data_global

loop_
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 section . 
;
?
;
 section 
;
Introduction
; 
;\
The dibenzo[b,e]azepine ring is an important pharmacophore in 
drug discovery and many of its derivatives exhibit a broad spectrum of 
biological activities (Van der Burg et al., 1970; Brogden 
et al., 1978; Nickolson & Wieringa, 1981; Berger et al., 1989; 
De Boer et al., 1996; Roeder et al., 1998; 
Andrés et al., 2002; Wikström et al., 2002). Consequently, 
a significant number of synthetic methods have been developed for the 
synthesis of new derivatives of this heterocyclic system (Moriconi & 
Maniscalco, 1972; Sasakura & Sugasawa, 1981; Stappers et al., 2002). 
In this context, we have recently developed a simple and practical synthetic 
route to obtain novel series of 6,11-dihydrodibenzo[b,e]azepines 
from readily available 2-allyl-N-benzyl-substituted anilines (Palma 
et al., 2004, 2010). To broaden the scope of this route, and in 
continuation of our research programme on the preparation of new potentially 
bioactive molecules containing the dihydrodibenzo[b,e]azepine 
nucleus, we have achieved a simple synthesis of three previously unknown
5-acetyl-11-ethyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-\
carboxylic acids. Here we report the molecular structures and supramolecular
assembly of three closely related compounds, namely
(6R*,11R*)-5-acetyl-11-ethyl-6,11-dihydro-5H-\
dibenzo[b,e]azepine-6-carboxylic acid, (I) (Fig. 1),
(6RS,11SR)-5-acetyl-11-ethyl-2-methyl-6,11-dihydro-5H-
dibenzo[b,e]azepine-6-carboxylic acid, (II) (Fig. 2), and
(6RS,11SR)-5-acetyl-11-ethyl-1,3-dimethyl-6,11-dihydro-
5H-dibenzo[b,e]azepine-6-carboxylic acid, (III) (Fig. 3),
the constitutions of which differ only in the presence of one methyl
substituent in (II) and two in (III), while there are none in (I). The
synthesis of compounds (I)--(III) was achieved by intramolecular
Friedel--Crafts alkylation of the corresponding methyl
2-[N-(2-allylaryl)acetamido]-2-phenylacetates using concentrated
sulfuric acid at 373 K (see scheme).
;
 section Experimental 
;
?
;
 subsection 'Synthesis and crystallization'
;
For the synthesis of each of (I)--(III), a suspension of the appropriately
substituted racemic methyl 2-[N-(2-allylaryl)acetamido]-2-phenylacetate
(see scheme) (1.0 g) in concentrated sulfuric acid (3 ml) was stirred at 373 K
for 7 min. The reaction mixture was cooled to ambient temperature by the
addition of ice and then extracted with ethyl acetate (3 × 50 ml). The
combined organic extracts were dried over anhydrous sodium sulfate and the
solvent was removed under reduced pressure. The resulting crude products were
subjected to column chromatographic purification over silica gel using
heptane--ethyl acetate--acetic acid (1:2:0.04 v/v/v).
Crystallization from ethyl acetate--ethanol (30:1 v/v) at
ambient temperature and in the presence of air gave colourless crystals of
(I)--(III), suitable for single-crystal X-ray diffraction. Compound (I): yield
35%, m.p. 449--450 K, HRMS m/z [M]⁺ found 309.1366,
C₁₉H₁₉NO₃ requires 309.1365. Compound (II): yield 20%, m.p. 460--462 K,
HRMS m/z [M]⁺ found 323.1525, C₂₀H₂₁NO₃ requires
323.1521. Compound (III): yield 41%, m.p. 497--499 K, HRMS m/z
[M]⁺ found 337.1653, C₂₁H₂₁NO₃ requires 337.1678.
;

 subsection Refinement
;
Crystal data, data collection and structure refinement details are summarized
in Table 1. All H atoms were located in difference maps and subsequently
treated as riding atoms. C-bound H atoms were permitted to ride in
geometrically idealized positions, with C---H = 0.95 (aromatic), 0.98 (CH₃),
0.99 (CH₂) or 1.00 Å (aliphatic C---H), and with Uiso(H) =
kUeq(C), where k = 1.5 for the methyl groups, which were
permitted to rotate but not to tilt, and 1.2 for all other C-bound H atoms.
O-bound H atoms were permitted to ride at the positions located in difference
maps with Uiso(H) = 1.5Ueq(O), giving the O---H distances
shown in Table 3. Several low-angle reflections, which had been wholly or
partially attenuated by the beam stop, were omitted from the final
refinements. The value of the Flack x parameter (Flack, 1983)
for (I)
was indeterminate (Flack & Bernardinelli, 2000); accordingly,
Friedel-equivalent reflections were merged prior to the final refinements.
Examination of the refined structures using PLATON (Spek, 2009)
showed
the presence of two small cavities in the structure of (II), centred at (1/2,
0, 1/2) and (1/2, 1/2, 0) and each of volume 24 Å³; these cavities are far
too small to contain any plausible solvent molecule but, nonetheless, the
largest peak in the difference map, 0.68 e Å⁻³ at (0.523, 0.482, 0.064),
was very close to one of the cavities. However, application of the SQUEEZE
procedure in PLATON revealed only one excess electron per cavity.
Accordingly, we regard both the difference peak and the excess electron count
as minor artefacts of the data.
;

 section 'Results and discussion'
;
The molecules of (I)--(III) all contain two stereogenic centres at atoms C6 and
C11 (Figs. 1--3). In (I), the exocyclcic substituents at atoms C6 and C11 have
a cis arrangement relative to the azepine ring, while those in (II) and
(III) have a trans arrangement. For each compound, the reference
molecule was selected as one having the R configuration at atom C6. On
this basis, the reference molecule of (I) has the R configuration at
atom C11, while those of (II) and (III) have the S configuration at
atom C11. Compounds (II) and (III) crystallize as racemic mixtures, as shown
by the centrosymmetric space group, but (I) crystallizes in the Sohnke space
group P2₁. Hence in the absence of twinning, for which no evidence
was found, each crystal of (I) contains only one enantiomorph. It was not
possible to determine the absolute configuration of the molecules in the
crystal of (I) which was selected for data collection, and hence the
configuration of the reference molecule was set to have the R
configuration at atom C6, just as for (II) and (III).

Since the methyl 2-[N-(2-allylaryl)acetamido]-2-phenylacetates used as
the precursors to (I)--(III) (see scheme) are all racemic, the crystallization
of (II) and (III) as racemic mixtures is unsurprising, and the method of
synthesis makes it probable that (I) is formed in solution as a racemic
mixture, which then crystallizes as a conglomerate rather than as a racemate.
More problematic is the difference in relative configurations at atoms C6 and
C11 between (I), (6R*,11R*), on the one hand and (II) and (III),
(6RS,11SR), on the other. Since the yields of the purified
crystallized products are all significantly less than 50% (see
Experimental), it is at least possible that the compounds may be formed
as diastereoisomeric mixtures, and that the stereoisomers reported here are
simply those which crystallized preferentially. However, it must be emphasized
that there is no direct evidence on this point, and so this suggestion must be
regarded as speculative.
;

#=============================================================

_audit_creation_date        'June 17, 2013'
_audit_creation_method      'from SHELXL-97'
_audit_update_record
;
;

#===================================================================
# 1. SUBMISSION DETAILS

_publ_contact_author_name       'Professor Christopher Glidewell'
_publ_contact_author_address
;
University of St Andrews
Fife KY16 9ST
Scotland
;

_publ_contact_author_phone      '+1334-463839'
_publ_contact_author_fax        '+1334-463808'
_publ_contact_author_email      cg@st-andrews.ac.uk

_publ_requested_journal         'Acta Crystallographica C'
_publ_requested_category        FO
_publ_requested_coeditor_name   ?

_publ_contact_letter
;
January 30, 2014

Please consider this CIF submission for publication in Acta Crystallographica
Section C.  All authors have seen and approved this submission.

The CIF has passed the Chester CHECKCIF routines and gives a 
satisfactory PRINTCIF file.  

Christopher Glidewell
;

#=====================================================================
# 2. PROCESSING SUMMARY  (IUCr Office Use Only)

_journal_date_recd_electronic     ?
_journal_date_to_coeditor         ?
_journal_date_from_coeditor       ?
_journal_date_accepted            ?
_journal_date_printers_first      ?
_journal_date_printers_final      ?
_journal_date_proofs_out          ?
_journal_date_proofs_in           ?
_journal_coeditor_name            ?
_journal_coeditor_code            ?
_journal_paper_doi                ?
_journal_paper_category           FO
_journal_coeditor_notes           ?
_journal_techeditor_code          ?
_iucr_compatibility_tag           ACTA95
_journal_techeditor_notes         ?
_journal_coden_ASTM               ACSCGG
_journal_name_full                'Acta Crystallographica, Section C'
_journal_year                     ?
_journal_volume                   ?
_journal_issue                    ?
_journal_page_first               ?
_journal_page_last                ?
_journal_suppl_publ_number        ?
_journal_suppl_publ_pages         ?

#=====================================================================
# 3. TITLE AND AUTHOR LIST

_publ_section_title
;
Three closely related dibenzazepine carboxylic acids: hydrogen-bonded
aggregation in one, two and three dimensions
;

loop_
_publ_author_name
_publ_author_address
_publ_author_email
_publ_author_footnote
'Sanabría, Carlos M.'
;  
Laboratorio de Síntesis Orgánica
Escuela de Química
Universidad Industrial de Santander
AA 678 Bucaramanga
Colombia
;
carmasasa@gmail.com
?
'Palma, Alirio'
;
Laboratorio de Síntesis Orgánica
Escuela de Química
Universidad Industrial de Santander
AA 678 Bucaramanga
Colombia
;
apalma@uis.edu.co
?
'Cobo, Justo'
;
Departamento de Química Inorgánica y Orgánica
Universidad de Jaén
23071 Jaén
Spain
;
jcobo@ujaen.es
?
'Glidewell, Christopher'
;
School of Chemistry
University of St Andrews
Fife KY16 9ST
Scotland
;
cg@st-andrews.ac.uk
?

#======================================================================
# 4. TEXT

_publ_section_synopsis
;\
In three
5-acetyl-11-ethyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-\
carboxylic acids, which differ only in the presence of zero, one or two
methyl substituents in one of the aryl rings, the hydrogen-bonded
supramolecular aggregation is respectively, two-, one- and three-dimensional.
;

_publ_section_keywords
;
crystal structure, dibenzo[b,e]azepine-6-carboxylic acid,
hydrogen bonding, hydrogen-bonded supramolecular aggregation
;

# Related literature generated by publCIF
_publ_section_related_literature
;
For related literature, see: Allen et al. (1987);
Andrés et al. (2002);
Batten & Robson (1998);
Berger et al. (1989);
Bernstein et al. (1995);
Bondi (1964);
Brogden et al. (1978);
Cremer & Pople (1975);
Davison, Kikolski, Lalancette & Thompson (2004);
Davison, Thompson & Lalancette (2004);
De Boer, Nefkens, van Helvoirt & van Delft (1996);
Entrena et al. (1997);
Evans & Boeyens (1989);
Ferguson et al. (1998a, 1998b);
Flack (1983);
Flack & Bernardinelli (2000);
Gregson et al. (2000);
Kikolski et al. (2006);
Malak et al. (2006);
Moriconi & Maniscalco (1972);
Nickolson & Wieringa (1981);
Palma et al. (2004, 2010);
Roeder et al. (1998);
Rowland & Taylor (1996);
Sasakura & Sugasawa (1981);
Spek (2009);
Stappers et al. (2002);
Thompson et al. (2004);
Van der Burg, Bonta, Delobelle, Ramon & Vargaftig (1970);
Wikström et al. (2002);
Wood et al. (2009).
;

_publ_section_abstract
;\
In the structure of
(6R*,11R*)-5-acetyl-11-ethyl-6,11-dihydro-5H-\
dibenzo[b,e]azepine-6-carboxylic acid, C₁₉H₁₉NO₃, (I),
the molecules are linked into sheets by a combination of O---H...O and
C---H...O hydrogen bonds; in the structure of the monomethyl analogue
(6RS,11SR)-5-acetyl-11-ethyl-2-methyl-6,11-dihydro-5H-\
dibenzo[b,e]azepine-6-carboxylic acid, C₂₀H₂₁NO₃, (II),
the molecules are linked into simple C(7) chains by O---H...O hydrogen
bonds; and in the structure of the dimethyl analogue
(6RS,11SR)-5-acetyl-11-ethyl-1,3-dimethyl-6,11-dihydro-\
5H-dibenzo[b,e]azepine-6-carboxylic acid,
C₂₁H₂₃NO₃, (III), a combination of O---H...O, C---H...O and
C---H...π(arene) hydrogen bonds links the molecules into a three-dimensional
framework structure. None of these structures exhibits the R₂²(8)
dimer motif characteristic of simple carboxylic acids.
;

_publ_section_references
;
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & 
Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1--S19.

Andrés, J. I., Alcázar, J., Alonso, J. M., Díaz, A., Fernández, J.,
Gil, P., Iturrino, L., Matesanz, E., Meert, T. F., Megens, A. & Sipido, 
V. K. (2002). Bioorg. Med. Chem. Lett. 12, 243--248.

Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37,
1460--1494.

Berger, J. G., Chang, W. K., Clader, J. W., Hou, D., Chipkin, R. E. & McPhail,
A. T. (1989). J. Med. Chem. 32, 1913--1921.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. 
Chem. Int. Ed. Engl. 34, 1555--1573.

Bondi, A. (1964). J. Phys. Chem. 68, 441--451.

Brogden, R. N., Heel, R. C., Speight, T. M. & Avery, G. S. (1978).
Drugs, 16, 273--301.

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., 
De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl.
Cryst. 38, 381--388.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97,
1354--1358.

Davison, M., Kikolski, E. M., Lalancette, R. A. & Thompson, H. W. (2004).
Acta Cryst. C60, o449--o451.

Davison, M., Thompson, H. W. & Lalancette, R. A. (2004). Acta Cryst.
C60, o242--o244.

De Boer, T. H., Nefkens, F., van Helvoirt, A. & van Delft, A. M. L. (1996).
J. Pharmacol. Exp. Ther. 277, 852--860.

Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000).
J. Appl. Cryst. 33, 893--898.

Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst. 36, 220--229.

Entrena, A., Campos, J., Gómez, J. A., Gallo, M. A. & Espinosa, A. (1997).
J. Org. Chem. 62, 337--349.

Evans, D. G. & Boeyens, J. C. A. (1989). Acta Cryst. B45,
581--590.

Ferguson, G., Glidewell, C., Gregson, R. M. & Meehan, P. R. (1998a).
Acta Cryst. B54, 129--138.

Ferguson, G., Glidewell, C., Gregson, R. M. & Meehan, P. R. (1998b).
Acta Cryst. B54, 139--150.

Flack, H. D. (1983). Acta Cryst. A39, 876--881.

Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33,
1143--1148.

Gregson, R. M., Glidewell, C., Ferguson, G. & Lough, A. J. (2000). Acta
Cryst. B56, 39--57.

Kikolski, E. M., Thompson, H. W. & Lalancette, R. A. (2006). 
Acta Cryst. C62, o397--o398.

Malak, M. H., Baker, D., Brunskill, A. P. J., Thompson, H. W. & Lalancette, R.
A. (2006). Acta Cryst. C62, o669--o670.

Moriconi, E. J. & Maniscalco, I. A. (1972). J. Org. Chem. 37,
208--215.

Nickolson, V. J. & Wieringa, J. H. (1981). J. Pharm. Pharmacol.
33, 760--766.

Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.

Palma, A., Galeano, N. & Bahsas, A. (2010). Synthesis, pp. 1291--1302.

Palma, A., Jaimes-Barajas, J., Kouznetsov, V. V., Stashenko, E., Bahsas, A. &
Amaro-Luis, J. (2004). Synlett, pp. 2721--2724.

Roeder, T., Degen, J. & Gewecke, M. (1998). Eur. J. Pharmacol.
349, 171--177.

Rowland, R. S. & Taylor, R. (1996). J. Phys. Chem. 100,
7384--7391.

Sasakura, K. & Sugasawa, T. (1981). Heterocycles, 15, 421--425.

Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.

Spek, A. L. (2009). Acta Cryst. D65, 148--155.

Stappers, F., Broeckx, R., Leurs, S., Van Den Bergh, L., Agten, J., 
Lambrechts, A., Van den Heurel, D. & De Smaele, D. (2002). Org. 
Process Res. Dev. 6, 911--914.

Thompson, H. W., Coté, M. L. & Lalancette, R. A. (2004). Acta Cryst.
C60, o727--o729.

Van der Burg, W. J., Bonta, I. L., Delobelle, J., Ramon, C. & Vargaftig, B.
(1970). J. Med. Chem. 13, 35--39.

Wikström, H. V., Mensonides-Harsema, M. M., Cremers, T. I. F. H., Moltzen, 
E. K. & Arnt, J. (2002). J. Med. Chem. 45, 3280--3285.

Wood, P. A., Allen, F. H. & Pidcock, E. (2009). CrystEngComm, 
11, 1563--1571.
;


_publ_section_figure_captions  
;
Fig. 1. The molecular structure of the (6R,11R) enantiomer of
(I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at
the 30% probability level.

Fig. 2. The molecular structure of the (6R,11S) enantiomer of
(II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at
the 30% probability level.

Fig. 3. The molecular structure of the (6R,11S) enantiomer of
(III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at
the 30% probability level.

Fig. 4. Part of the crystal structure of (II), showing the formation of a
hydrogen-bonded (dashed lines) chain parallel to [010]. For the sake of
clarity, H atoms not involved in the motifs shown have been omitted. Atoms
marked with an asterisk (*), a hash (#), a dollar sign ($) or an ampersand (&)
are at the symmetry positions (-x+1, y+1/2, -z+1/2), 
(-x+1, y-1/2, -z+1/2), (x, y+1, z) 
and (x, y-1, z), respectively.

Fig. 5. A stereoview of part of the crystal structure of (I), showing the
formation of a hydrogen-bonded (dashed lines) sheet parallel to (10\=1). 
For the sake of clarity, H atoms not involved in the motifs shown have been
omitted.

Fig. 6. A stereoview of part of the crystal structure of (III), showing the
formation of a hydrogen-bonded (dashed lines) sheet of R₄⁴(30)
rings parallel to (10\=1) and built from a combination of O---H...O and
C---H...O hydrogen bonds. For the sake of clarity, H atoms not involved in the
motifs shown have been omitted.

Fig. 7. A stereoview of part of the crystal structure of (III), showing the
formation of a chain parallel to [100] built from C---H...π(arene) hydrogen
bonds (dashed lines). For the sake of clarity, H atoms not involved in the
motif shown have been omitted.
;

_publ_section_table_legends
;
Table 1.  Experimental details

Table 2. Selected geometric parameters (Å, °) for (I)--(III)

Table 3. Hydrogen bonds and short intermolecular contacts (Å, °) for 
(I)--(III)
;
_publ_section_acknowledgements
;
The authors thank the Centro de Instrumentación Científico-Técnica of the
Universidad de Jaén and the staff for the data collection. AP and CMS thank
Colciencias for financial support (grant No. 1102-521-28229). JC thanks the
Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain)
and the Universidad de Jaén for financial support.
;

#=====================================================================


#=====================================================================

loop_
_publ_manuscript_incl_extra_item
'_geom_extra_tableA_col_1'
'_geom_extra_tableA_col_2'
'_geom_extra_tableA_col_3'
'_geom_extra_tableA_col_4'
'_geom_extra_table_head_A'    
'_geom_table_footnote_A'      
'_geom_extra_tableB_col_1'
'_geom_extra_tableB_col_2'
'_geom_extra_tableB_col_3'
'_geom_extra_tableB_col_4'
'_geom_extra_tableB_col_5'
'_geom_extra_tableB_col_6'
'_geom_extra_table_head_B'    
'_geom_table_footnote_B'      

_geom_extra_table_head_A                        
;
Selected geometric parameters (\%A, \%) for (I)--(III)
;

loop_
_geom_extra_tableA_col_1
_geom_extra_tableA_col_2
_geom_extra_tableA_col_3
_geom_extra_tableA_col_4
"Bond lengths and angles" ? ? ?
Parameter    (I)    (II)        (III)
N5---C51   1.354(3)   1.356(3)   1.358(3)
C51---O51  1.249(3)   1.241(3)   1.246(3)
C61---O61  1.328(3)   1.325(3)   1.319(3)
C61---O62  1.207((3)  1.204(3)   1.207(3)
? ? ? ?
N5---C6---C61---O61    -155.01(18) -49.6(2)  159.0(2)
N5---C6---C61---O62      24.4(3)   131.7(2)  -24.6(3)
C6---N5---C51---O51       0.7(3)     6.0(3)    3.1(4)
C6---N5---C51---C52     179.1(2)  -175.6(2) -179.2(2)
C10---C10a---C11---C111    -18.3(3)  -96.7(2) -89.4(3)
C10a---C11---C111---C112  -168.0(2)   71.1(2) 169.2(2)
? ? ? ?
"Puckering parameters for seven-membered rings" ? ? ?
'<i>Q</i>' 1.079(3)  0.842(2)  0.800(3)
'\f~2~'    44.93(14) 23.01(13) 17.2(2) 
'\f~3~'    274.6(8)  311.3(4)  313.2(5)

_geom_table_footnote_A
;
Ring-puckering parameters are calculated for the
atom sequence N5--C4a--C11a--C11--C10a---C6a---C6
;

_geom_extra_table_head_B                        
;
Hydrogen bonds and short intermolecular contacts (\%A, \%) for (I)--(III)
;

loop_
_geom_extra_tableB_col_1
_geom_extra_tableB_col_2
_geom_extra_tableB_col_3
_geom_extra_tableB_col_4
_geom_extra_tableB_col_5
_geom_extra_tableB_col_6
Compound  '<i>D</i>---H...<i>A</i>'  '<i>D</i>---H' 'H...<i>A</i>'
'<i>D</i>...<i>A</i>' '<i>D</i>---H...<i>A</i>'
(I)    'O61---H61...O51^i^'        0.86  1.83  2.672(2)  167
?      'C2---H2...O51^ii^'         0.95  2.49  3.309(3)  144
?      'C112---H12A...O62^iii^'    0.98  2.46  3.418(4)  165
(II)   'O61---H61...O51^iv^'       0.92  1.67  2.572(2)  167 
?      'C4---H4...O62^v^'          0.95  2.58  3.220(3)  125
?      'C8---H8...O62^vi^'         0.95  2.58  3.405(3)  145
(III)  'O61---H61...O51^vii^'      0.86  1.76  2.575(3)  156
?      'C9---H9...O62^viii^'       0.95  2.50  3.329(3)  145
?      'C8---H8...<i>Cg</i>1^ix^'  0.95  2.75  3.569(3)  144

_geom_table_footnote_B
;
<i>Cg</i>1 represents the centroid of the ring C1--C4/C4a/C11a.
Symmetry codes: (i) -x, y - 1/2, -z; (ii) x + 1, y, z + 1;
(iii) -x + 1, y + 1/2, -z + 1; (iv) -x + 1, y + 1/2, -z + 1/2;
(v) x, -y + 3/2, z - 1/2; (vi) x, -y + 3/2, z + 1/2; (vii) x + 1/2, -y + 3/2,
z + 1/2; (viii) -x + 3/2, y - 1/2, -z + 1/2; (ix) x + 1, y, z.
;

#=====================================================================

data_I

#=====================================================================
# 5. Chemical Data

_chemical_name_systematic
;\
(6R*,11R*)-5-Acetyl-11-ethyl-6,11-dihydro-5H-\
dibenzo[b,e]azepine-6-carboxylic acid
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C19 H19 N O3' 
_chemical_formula_sum             'C19 H19 N O3' 
_chemical_formula_weight          309.35 
_chemical_compound_source         'synthesised by authors, see text'
_chemical_formula_iupac           'C19 H19 N O3' 

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P 21'
_symmetry_space_group_name_Hall   'P 2yb'

loop_
 _symmetry_equiv_pos_as_xyz
'x, y, z' 
 '-x, y+1/2, -z' 

_cell_length_a                    8.8053(3) 
_cell_length_b                    10.9821(4) 
_cell_length_c                    9.0080(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  118.510(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      765.45(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1853
_cell_measurement_theta_min       3.20
_cell_measurement_theta_max       27.50

_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.26
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.342
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              328
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details    '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min   0.977
_exptl_absorpt_correction_T_max   0.991

_exptl_special_details
?

_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_source          'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method        'φ and ω'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_number          0
_diffrn_standards_decay_%         0

_diffrn_reflns_number             13276 
_diffrn_reflns_av_R_equivalents   0.0486 
_diffrn_reflns_av_sigmaI/netI     0.0321 
_diffrn_reflns_limit_h_min       -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min       -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min       -11 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          3.71
_diffrn_reflns_theta_max          27.50
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_max    0.997
_diffrn_measured_fraction_theta_full   0.997
_reflns_number_total              1851
_reflns_number_gt                 1638
_reflns_threshold_expression      I>2σ(I)

_computing_data_collection        'COLLECT (Nonius, 1998)' 
_computing_cell_refinement        
'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_reduction         
'EVALCCD (Duisenberg et al., 2003)'
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'  
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material 
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;

#=========================================================================
# 8. Refinement Data

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0351P)²+0.1657P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_chemical_absolute_configuration  unk
_refine_ls_number_reflns          1851 
_refine_ls_number_parameters      210 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0455 
_refine_ls_R_factor_gt            0.0360 
_refine_ls_wR_factor_ref          0.0807 
_refine_ls_wR_factor_gt           0.0772 
_refine_ls_goodness_of_fit_ref    1.146 
_refine_ls_restrained_S_all       1.146 
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_diff_density_max          0.209
_refine_diff_density_min         -0.240

#=========================================================================
# 9. Atomic Coordinates and Displacement Parameters

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.6424(3) 0.5942(2) 0.7939(3) 0.0186(5) Uani 1 1 d . . . 
H1 H 0.6599 0.6154 0.9031 0.022 Uiso 1 1 calc R . . 
C2 C 0.7828(3) 0.5595(2) 0.7731(3) 0.0211(5) Uani 1 1 d . . . 
H2 H 0.8953 0.5589 0.8678 0.025 Uiso 1 1 calc R . . 
C3 C 0.7604(3) 0.5255(2) 0.6149(3) 0.0202(5) Uani 1 1 d . . . 
H3 H 0.8563 0.4993 0.6019 0.024 Uiso 1 1 calc R . . 
C4 C 0.5955(3) 0.5306(2) 0.4757(3) 0.0166(5) Uani 1 1 d . . . 
H4 H 0.5780 0.5079 0.3669 0.020 Uiso 1 1 calc R . . 
C4a C 0.4576(3) 0.5687(2) 0.4973(3) 0.0142(5) Uani 1 1 d . . . 
N5 N 0.2883(2) 0.58197(17) 0.3533(2) 0.0132(4) Uani 1 1 d . . . 
C6 C 0.1469(3) 0.4966(2) 0.3244(3) 0.0128(4) Uani 1 1 d . . . 
H6 H 0.0389 0.5461 0.2831 0.015 Uiso 1 1 calc R . . 
C6a C 0.1714(3) 0.4295(2) 0.4842(3) 0.0145(5) Uani 1 1 d . . . 
C7 C 0.1243(3) 0.3077(2) 0.4737(3) 0.0174(5) Uani 1 1 d . . . 
H7 H 0.0884 0.2652 0.3704 0.021 Uiso 1 1 calc R . . 
C8 C 0.1286(3) 0.2465(2) 0.6107(3) 0.0189(5) Uani 1 1 d . . . 
H8 H 0.0977 0.1628 0.6008 0.023 Uiso 1 1 calc R . . 
C9 C 0.1780(3) 0.3073(2) 0.7616(3) 0.0188(5) Uani 1 1 d . . . 
H9 H 0.1759 0.2670 0.8540 0.023 Uiso 1 1 calc R . . 
C10 C 0.2305(3) 0.4277(2) 0.7762(3) 0.0185(5) Uani 1 1 d . . . 
H10 H 0.2674 0.4685 0.8808 0.022 Uiso 1 1 calc R . . 
C10a C 0.2307(3) 0.4909(2) 0.6412(3) 0.0151(5) Uani 1 1 d . . . 
C11 C 0.3097(3) 0.6185(2) 0.6677(3) 0.0150(5) Uani 1 1 d . . . 
H11 H 0.2307 0.6694 0.5686 0.018 Uiso 1 1 calc R . . 
C11a C 0.4763(3) 0.5982(2) 0.6566(3) 0.0145(5) Uani 1 1 d . . . 
C51 C 0.2534(3) 0.6720(2) 0.2388(3) 0.0142(5) Uani 1 1 d . . . 
O51 O 0.10670(19) 0.68043(16) 0.11339(19) 0.0180(4) Uani 1 1 d . . . 
C52 C 0.3950(3) 0.7609(2) 0.2675(3) 0.0189(5) Uani 1 1 d . . . 
H52A H 0.4784 0.7219 0.2397 0.028 Uiso 1 1 calc R . . 
H52B H 0.4537 0.7862 0.3862 0.028 Uiso 1 1 calc R . . 
H52C H 0.3452 0.8324 0.1952 0.028 Uiso 1 1 calc R . . 
C61 C 0.1208(3) 0.4093(2) 0.1806(3) 0.0145(5) Uani 1 1 d . . . 
O61 O -0.0387(2) 0.36474(17) 0.10291(19) 0.0186(4) Uani 1 1 d . . . 
H61 H -0.0487 0.3107 0.0297 0.028 Uiso 1 1 d R . . 
O62 O 0.2327(2) 0.38608(17) 0.1438(2) 0.0224(4) Uani 1 1 d . . . 
C111 C 0.3325(3) 0.6837(2) 0.8280(3) 0.0202(5) Uani 1 1 d . . . 
H11A H 0.2247 0.6761 0.8362 0.024 Uiso 1 1 calc R . . 
H11B H 0.4266 0.6440 0.9284 0.024 Uiso 1 1 calc R . . 
C112 C 0.3752(3) 0.8181(2) 0.8272(3) 0.0229(5) Uani 1 1 d . . . 
H12A H 0.4821 0.8260 0.8195 0.034 Uiso 1 1 calc R . . 
H12B H 0.3905 0.8565 0.9317 0.034 Uiso 1 1 calc R . . 
H12C H 0.2804 0.8583 0.7300 0.034 Uiso 1 1 calc R . . 

loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.0214(12) 0.0168(12) 0.0133(11) -0.0003(10) 0.0048(10) -0.0021(10) 
C2 0.0163(12) 0.0170(13) 0.0222(13) 0.0035(10) 0.0027(10) -0.0025(9) 
C3 0.0158(11) 0.0198(13) 0.0252(13) 0.0052(10) 0.0101(11) 0.0018(10) 
C4 0.0191(11) 0.0145(12) 0.0168(11) 0.0012(9) 0.0091(10) -0.0002(9) 
C4a 0.0138(11) 0.0128(12) 0.0136(11) 0.0021(9) 0.0045(10) -0.0010(8) 
N5 0.0120(9) 0.0137(10) 0.0117(9) 0.0010(8) 0.0038(8) -0.0010(7) 
C6 0.0117(10) 0.0148(11) 0.0113(10) -0.0002(9) 0.0049(9) -0.0006(8) 
C6a 0.0133(11) 0.0176(12) 0.0136(11) 0.0004(9) 0.0071(9) 0.0010(9) 
C7 0.0156(11) 0.0201(12) 0.0151(11) -0.0019(9) 0.0061(9) -0.0004(9) 
C8 0.0177(12) 0.0162(12) 0.0217(12) 0.0009(10) 0.0085(10) -0.0028(10) 
C9 0.0173(12) 0.0222(13) 0.0183(12) 0.0054(10) 0.0097(10) 0.0008(10) 
C10 0.0172(12) 0.0242(13) 0.0135(11) -0.0006(10) 0.0069(10) 0.0020(10) 
C10a 0.0125(10) 0.0167(11) 0.0162(11) 0.0002(9) 0.0068(9) 0.0006(9) 
C11 0.0152(11) 0.0167(12) 0.0135(11) -0.0015(9) 0.0073(9) -0.0009(9) 
C11a 0.0184(12) 0.0098(10) 0.0156(11) 0.0006(9) 0.0083(10) -0.0010(9) 
C51 0.0168(11) 0.0142(11) 0.0121(11) -0.0020(9) 0.0074(9) 0.0004(9) 
O51 0.0161(8) 0.0186(9) 0.0150(8) 0.0025(7) 0.0040(7) 0.0005(7) 
C52 0.0207(12) 0.0162(12) 0.0194(12) 0.0029(10) 0.0092(10) -0.0010(10) 
C61 0.0176(11) 0.0127(11) 0.0117(10) 0.0022(9) 0.0058(9) 0.0001(9) 
O61 0.0176(8) 0.0213(9) 0.0150(8) -0.0065(7) 0.0062(7) -0.0045(7) 
O62 0.0221(9) 0.0252(10) 0.0241(9) -0.0062(8) 0.0144(8) -0.0024(7) 
C111 0.0243(12) 0.0195(13) 0.0176(12) -0.0036(11) 0.0106(10) -0.0018(11) 
C112 0.0265(13) 0.0208(13) 0.0248(13) -0.0065(10) 0.0151(11) -0.0031(10) 

#=========================================================================
# 10. Molecular Geometry

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.388(4) . ? 
C1 C11a 1.395(3) . ? 
C1 H1 0.9500 . ? 
C2 C3 1.393(4) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.395(3) . ? 
C3 H3 0.9500 . ? 
C4 C4a 1.383(3) . ? 
C4 H4 0.9500 . ? 
C4a C11a 1.402(3) . ? 
C4a N5 1.442(3) . ? 
N5 C51 1.354(3) . ? 
N5 C6 1.479(3) . ? 
C6 C6a 1.538(3) . ? 
C6 C61 1.538(3) . ? 
C6 H6 1.0000 . ? 
C6a C7 1.390(3) . ? 
C6a C10a 1.423(3) . ? 
C7 C8 1.390(3) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.386(3) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.386(3) . ? 
C9 H9 0.9500 . ? 
C10 C10a 1.401(3) . ? 
C10 H10 0.9500 . ? 
C10a C11 1.532(3) . ? 
C11 C11a 1.533(3) . ? 
C11 C111 1.536(3) . ? 
C11 H11 1.0000 . ? 
C51 O51 1.249(3) . ? 
C51 C52 1.506(3) . ? 
C52 H52A 0.9800 . ? 
C52 H52B 0.9800 . ? 
C52 H52C 0.9800 . ? 
C61 O62 1.207(3) . ? 
C61 O61 1.328(3) . ? 
O61 H61 0.8602 . ? 
C111 C112 1.523(4) . ? 
C111 H11A 0.9900 . ? 
C111 H11B 0.9900 . ? 
C112 H12A 0.9800 . ? 
C112 H12B 0.9800 . ? 
C112 H12C 0.9800 . ? 

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C11a 120.9(2) . . ? 
C2 C1 H1 119.5 . . ? 
C11a C1 H1 119.5 . . ? 
C1 C2 C3 120.7(2) . . ? 
C1 C2 H2 119.6 . . ? 
C3 C2 H2 119.6 . . ? 
C2 C3 C4 119.1(2) . . ? 
C2 C3 H3 120.4 . . ? 
C4 C3 H3 120.4 . . ? 
C4a C4 C3 119.6(2) . . ? 
C4a C4 H4 120.2 . . ? 
C3 C4 H4 120.2 . . ? 
C4 C4a C11a 122.1(2) . . ? 
C4 C4a N5 120.27(19) . . ? 
C11a C4a N5 117.61(19) . . ? 
C51 N5 C4a 121.36(18) . . ? 
C51 N5 C6 117.57(18) . . ? 
C4a N5 C6 121.06(17) . . ? 
N5 C6 C6a 114.16(18) . . ? 
N5 C6 C61 108.54(17) . . ? 
C6a C6 C61 112.80(19) . . ? 
N5 C6 H6 107.0 . . ? 
C6a C6 H6 107.0 . . ? 
C61 C6 H6 107.0 . . ? 
C7 C6a C10a 118.7(2) . . ? 
C7 C6a C6 119.6(2) . . ? 
C10a C6a C6 121.6(2) . . ? 
C8 C7 C6a 121.6(2) . . ? 
C8 C7 H7 119.2 . . ? 
C6a C7 H7 119.2 . . ? 
C9 C8 C7 120.0(2) . . ? 
C9 C8 H8 120.0 . . ? 
C7 C8 H8 120.0 . . ? 
C8 C9 C10 119.2(2) . . ? 
C8 C9 H9 120.4 . . ? 
C10 C9 H9 120.4 . . ? 
C9 C10 C10a 122.0(2) . . ? 
C9 C10 H10 119.0 . . ? 
C10a C10 H10 119.0 . . ? 
C10 C10a C6a 118.4(2) . . ? 
C10 C10a C11 120.5(2) . . ? 
C6a C10a C11 120.8(2) . . ? 
C10a C11 C11a 103.51(18) . . ? 
C10a C11 C111 114.78(19) . . ? 
C11a C11 C111 115.41(19) . . ? 
C10a C11 H11 107.6 . . ? 
C11a C11 H11 107.6 . . ? 
C111 C11 H11 107.6 . . ? 
C1 C11a C4a 117.4(2) . . ? 
C1 C11a C11 125.3(2) . . ? 
C4a C11a C11 116.87(19) . . ? 
O51 C51 N5 120.3(2) . . ? 
O51 C51 C52 121.4(2) . . ? 
N5 C51 C52 118.30(19) . . ? 
C51 C52 H52A 109.5 . . ? 
C51 C52 H52B 109.5 . . ? 
H52A C52 H52B 109.5 . . ? 
C51 C52 H52C 109.5 . . ? 
H52A C52 H52C 109.5 . . ? 
H52B C52 H52C 109.5 . . ? 
O62 C61 O61 125.0(2) . . ? 
O62 C61 C6 123.3(2) . . ? 
O61 C61 C6 111.64(18) . . ? 
C61 O61 H61 110.7 . . ? 
C112 C111 C11 111.7(2) . . ? 
C112 C111 H11A 109.3 . . ? 
C11 C111 H11A 109.3 . . ? 
C112 C111 H11B 109.3 . . ? 
C11 C111 H11B 109.3 . . ? 
H11A C111 H11B 108.0 . . ? 
C111 C112 H12A 109.5 . . ? 
C111 C112 H12B 109.5 . . ? 
H12A C112 H12B 109.5 . . ? 
C111 C112 H12C 109.5 . . ? 
H12A C112 H12C 109.5 . . ? 
H12B C112 H12C 109.5 . . ? 

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C11a C1 C2 C3 -1.3(4) . . . . ? 
C1 C2 C3 C4 2.1(4) . . . . ? 
C2 C3 C4 C4a -0.1(4) . . . . ? 
C3 C4 C4a C11a -2.7(4) . . . . ? 
C3 C4 C4a N5 176.0(2) . . . . ? 
C4 C4a N5 C51 -70.0(3) . . . . ? 
C11a C4a N5 C51 108.7(2) . . . . ? 
C4 C4a N5 C6 109.3(2) . . . . ? 
C11a C4a N5 C6 -72.0(3) . . . . ? 
C51 N5 C6 C6a -158.55(19) . . . . ? 
C4a N5 C6 C6a 22.1(3) . . . . ? 
C51 N5 C6 C61 74.7(2) . . . . ? 
C4a N5 C6 C61 -104.7(2) . . . . ? 
N5 C6 C6a C7 -141.2(2) . . . . ? 
C61 C6 C6a C7 -16.7(3) . . . . ? 
N5 C6 C6a C10a 42.9(3) . . . . ? 
C61 C6 C6a C10a 167.43(19) . . . . ? 
C10a C6a C7 C8 2.2(3) . . . . ? 
C6 C6a C7 C8 -173.8(2) . . . . ? 
C6a C7 C8 C9 1.0(4) . . . . ? 
C7 C8 C9 C10 -3.0(3) . . . . ? 
C8 C9 C10 C10a 1.8(3) . . . . ? 
C9 C10 C10a C6a 1.4(3) . . . . ? 
C9 C10 C10a C11 -172.7(2) . . . . ? 
C7 C6a C10a C10 -3.4(3) . . . . ? 
C6 C6a C10a C10 172.6(2) . . . . ? 
C7 C6a C10a C11 170.7(2) . . . . ? 
C6 C6a C10a C11 -13.4(3) . . . . ? 
C10 C10a C11 C11a 108.4(2) . . . . ? 
C6a C10a C11 C11a -65.6(3) . . . . ? 
C10 C10a C11 C111 -18.3(3) . . . . ? 
C6a C10a C11 C111 167.7(2) . . . . ? 
C2 C1 C11a C4a -1.4(3) . . . . ? 
C2 C1 C11a C11 171.5(2) . . . . ? 
C4 C4a C11a C1 3.4(3) . . . . ? 
N5 C4a C11a C1 -175.3(2) . . . . ? 
C4 C4a C11a C11 -170.1(2) . . . . ? 
N5 C4a C11a C11 11.2(3) . . . . ? 
C10a C11 C11a C1 -103.1(3) . . . . ? 
C111 C11 C11a C1 23.1(4) . . . . ? 
C10a C11 C11a C4a 69.8(2) . . . . ? 
C111 C11 C11a C4a -163.9(2) . . . . ? 
C4a N5 C51 O51 178.7(2) . . . . ? 
C6 N5 C51 O51 -0.7(3) . . . . ? 
C4a N5 C51 C52 -1.5(3) . . . . ? 
C6 N5 C51 C52 179.1(2) . . . . ? 
N5 C6 C61 O62 24.4(3) . . . . ? 
C6a C6 C61 O62 -103.1(3) . . . . ? 
N5 C6 C61 O61 -155.01(18) . . . . ? 
C6a C6 C61 O61 77.5(2) . . . . ? 
C10a C11 C111 C112 -168.0(2) . . . . ? 
C11a C11 C111 C112 71.7(3) . . . . ? 

loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
 _geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
# D   H    A   D-H   H...A  D...A    D-H...A  symm  publ
# -   -    -   ---   -----  -----    -------  ----  ----
 O61  H61  O51 0.86  1.83   2.672(2) 167      2_545 no
 C2   H2   O51 0.95  2.49   3.309(3) 144      1_656 no
 C112 H12A O62 0.98  2.46   3.418(4) 165      2_656 no

#======================================================================


_iucr_refine_instructions_details
;
TITL CM45F8
CELL  0.71073   8.8053  10.9821   9.0080   90.000  118.510   90.000
ZERR     2.00   0.0003   0.0004   0.0006    0.000    0.003    0.000
LATT  -1
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    N    O
UNIT  38   38   2    6
MERG   4
OMIT    -2.00 55.00
FMAP   2
PLAN   20
SIZE     0.10   0.14   0.26
ACTA
BOND   $H
CONF
HTAB
OMIT 1 1 0
OMIT -1 1 1
LIST   4
L.S.   8
TEMP  -153.00
WGHT    0.035100    0.165700
FVAR       1.39751
C1    1    0.642443    0.594154    0.793875    11.00000    0.02140    0.01683 =
         0.01327   -0.00034    0.00478   -0.00213
AFIX  43
H1    2    0.659873    0.615425    0.903129    11.00000   -1.20000
AFIX   0
C2    1    0.782781    0.559463    0.773119    11.00000    0.01629    0.01699 =
         0.02217    0.00353    0.00273   -0.00253
AFIX  43
H2    2    0.895282    0.558863    0.867841    11.00000   -1.20000
AFIX   0
C3    1    0.760432    0.525515    0.614880    11.00000    0.01584    0.01980 =
         0.02524    0.00519    0.01015    0.00176
AFIX  43
H3    2    0.856262    0.499287    0.601936    11.00000   -1.20000
AFIX   0
C4    1    0.595473    0.530554    0.475729    11.00000    0.01912    0.01446 =
         0.01678    0.00125    0.00906   -0.00022
AFIX  43
H4    2    0.577979    0.507917    0.366895    11.00000   -1.20000
AFIX   0
C4a   1    0.457563    0.568724    0.497261    11.00000    0.01382    0.01282 =
         0.01356    0.00214    0.00450   -0.00103
N5    3    0.288314    0.581975    0.353266    11.00000    0.01198    0.01373 =
         0.01166    0.00100    0.00383   -0.00105
C6    1    0.146917    0.496600    0.324411    11.00000    0.01169    0.01480 =
         0.01126   -0.00015    0.00490   -0.00064
AFIX  13
H6    2    0.038938    0.546079    0.283111    11.00000   -1.20000
AFIX   0
C6a   1    0.171355    0.429513    0.484153    11.00000    0.01329    0.01757 =
         0.01355    0.00044    0.00709    0.00104
C7    1    0.124326    0.307677    0.473724    11.00000    0.01560    0.02008 =
         0.01506   -0.00192    0.00609   -0.00038
AFIX  43
H7    2    0.088369    0.265234    0.370398    11.00000   -1.20000
AFIX   0
C8    1    0.128614    0.246451    0.610695    11.00000    0.01770    0.01619 =
         0.02174    0.00087    0.00851   -0.00276
AFIX  43
H8    2    0.097654    0.162826    0.600826    11.00000   -1.20000
AFIX   0
C9    1    0.178015    0.307296    0.761647    11.00000    0.01733    0.02220 =
         0.01834    0.00538    0.00971    0.00082
AFIX  43
H9    2    0.175933    0.267006    0.853983    11.00000   -1.20000
AFIX   0
C10   1    0.230502    0.427676    0.776204    11.00000    0.01718    0.02418 =
         0.01352   -0.00059    0.00685    0.00203
AFIX  43
H10   2    0.267411    0.468531    0.880811    11.00000   -1.20000
AFIX   0
C10a  1    0.230749    0.490913    0.641243    11.00000    0.01246    0.01667 =
         0.01623    0.00016    0.00684    0.00056
C11   1    0.309683    0.618540    0.667747    11.00000    0.01523    0.01672 =
         0.01353   -0.00154    0.00732   -0.00093
AFIX  13
H11   2    0.230748    0.669420    0.568637    11.00000   -1.20000
AFIX   0
C11a  1    0.476255    0.598216    0.656614    11.00000    0.01843    0.00976 =
         0.01565    0.00055    0.00829   -0.00105
 
C51   1    0.253368    0.672019    0.238787    11.00000    0.01680    0.01421 =
         0.01210   -0.00198    0.00743    0.00042
O51   4    0.106700    0.680430    0.113386    11.00000    0.01608    0.01859 =
         0.01499    0.00249    0.00402    0.00048
C52   1    0.395047    0.760869    0.267480    11.00000    0.02070    0.01620 =
         0.01940    0.00286    0.00916   -0.00096
AFIX 137
H52A  2    0.478434    0.721879    0.239710    11.00000   -1.50000
H52B  2    0.453745    0.786182    0.386198    11.00000   -1.50000
H52C  2    0.345169    0.832372    0.195207    11.00000   -1.50000
AFIX   0
 
C61   1    0.120819    0.409307    0.180594    11.00000    0.01761    0.01275 =
         0.01168    0.00224    0.00579    0.00012
O61   4   -0.038667    0.364738    0.102914    11.00000    0.01765    0.02128 =
         0.01495   -0.00650    0.00617   -0.00452
AFIX   3
H61   2   -0.048669    0.310674    0.029683    11.00000   -1.50000
AFIX   0
O62   4    0.232707    0.386081    0.143759    11.00000    0.02212    0.02519 =
         0.02409   -0.00624    0.01436   -0.00241
 
C111  1    0.332488    0.683745    0.827992    11.00000    0.02428    0.01948 =
         0.01756   -0.00357    0.01064   -0.00184
AFIX  23
H11A  2    0.224713    0.676059    0.836195    11.00000   -1.20000
H11B  2    0.426599    0.644010    0.928445    11.00000   -1.20000
AFIX   0
C112  1    0.375182    0.818096    0.827218    11.00000    0.02653    0.02084 =
         0.02483   -0.00653    0.01506   -0.00313
AFIX 137
H12A  2    0.482058    0.825982    0.819501    11.00000   -1.50000
H12B  2    0.390518    0.856476    0.931702    11.00000   -1.50000
H12C  2    0.280435    0.858256    0.729953    11.00000   -1.50000
HKLF 4
 
REM  CM45F8
REM R1 =  0.0360 for   1638 Fo > 4sig(Fo)  and  0.0455 for all   1851 data
REM    210 parameters refined using      1 restraints
 
END  
     
WGHT      0.0351      0.1657 
REM Highest difference peak  0.209,  deepest hole -0.240,  1-sigma level  0.047
Q1    1   0.1374  0.4513  0.2451  11.00000  0.05    0.21
Q2    1   0.5006  0.7306  0.7023  11.00000  0.05    0.18
Q3    1   0.2063  0.4551  0.5588  11.00000  0.05    0.18
Q4    1   0.2180  0.5354  0.3391  11.00000  0.05    0.17
Q5    1   0.6831  0.6851  0.9667  11.00000  0.05    0.17
Q6    1   0.0732  0.0693  0.6018  11.00000  0.05    0.17
Q7    1   0.6020  0.8659  0.3678  11.00000  0.05    0.17
Q8    1   0.5105  0.9084  0.2589  11.00000  0.05    0.16
Q9    1   0.5204  0.7451  0.5750  11.00000  0.05    0.16
Q10   1   0.4683  0.5985  0.5722  11.00000  0.05    0.16
Q11   1   0.6412  0.7835  0.4017  11.00000  0.05    0.15
Q12   1   0.1569  0.5382  0.0448  11.00000  0.05    0.15
Q13   1   0.4688  0.7959  0.5012  11.00000  0.05    0.15
Q14   1   0.7544  0.4002  0.4802  11.00000  0.05    0.15
Q15   1   0.5796  0.8187  0.5697  11.00000  0.05    0.15
Q16   1   0.3044  0.2205  0.6197  11.00000  0.05    0.15
Q17   1   0.1886  0.2243  1.0318  11.00000  0.05    0.15
Q18   1   0.2287  0.7530  0.4991  11.00000  0.05    0.14
Q19   1   0.8512  0.4325  0.9053  11.00000  0.05    0.14
Q20   1   0.5138  0.7749  0.3766  11.00000  0.05    0.14
;
#======================================================================
#                         END of CIF
#======================================================================

