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Acta Cryst. (1991). A47, 655-685
This is an extract from a CIF, generated by the program CIFIO (Hall, 1990), and submitted to Acta Crystallographica Section C for publication (Willis, Beckwith & Tozer, 1991). This CIF contains more data than required for publication purposes. Items requested for inclusion in this CIF but not present in the Xtal binary file are flagged with a `?'.
data_TOZ
_audit_creation_date 91-03-20
_audit_creation_method
from_xtal_archive_file_using_CIFIO
_audit_update_record
; 91-04-09 text and data added by Tony Willis.
91-04-15 rec'd by co-editor with diagram as ms. HL7.
91-04-17 adjustments based on first referees report.
91-04-18 adjustments based on second referees report.
;
_chemical_name_systematic
;
trans-3-Benzoyl-2-(tert-butyl)-4-(isobutyl)-
1,3-oxazolidin-5-one
;
_chemical_formula_moiety 'C18 H25 N O3'
_chemical_formula_sum 'C18 H25 N O3'
_chemical_formula_weight 303.40
_chemical_melting_point ?
_computing_data_collection
'Philips PW1100/20 software 1976'
_computing_cell_refinement
'LATCON (Xtal: Schwarzenbach & King)'
_computing_data_reduction
'pwredu (McLaughlin) ADDREF SORTRF (Xtal)'
_computing_structure_solution
'SHELXS86 (Sheldrick)'
_computing_structure_refinement
'SHELX76 (Sheldrick) CRYLSQ (Xtal: Olthof)'
_computing_publication_material
'BONDLA CIFIO (Xtal: Hall)
_cell_length_a 5.959(1)
_cell_length_b 14.956(1)
_cell_length_c 19.737(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1759.0(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 293
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 25
_cell_measurement_theta_max 31
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall P_2ac_2ab
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z 1/2-x,-y,1/2+z
1/2+x,1/2-y,-z -x,1/2+y,1/2-z
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.146
_exptl_crystal_density_meas ?
_exptl_crystal_F_000 656
_exptl_absorpt_coefficient_mu 5.9
_exptl_absorpt_correction_type 'shelx76 gaussian'
_exptl_absorpt_correction_T_min .933
_exptl_absorpt_correction_T_max .824
_diffrn_special_details
;
\q scan width (1.0 + 0.14tan\q)\%, \q scan rate
1.2\% per min.Background counts for 5 s on each
side every scan.
;
_diffrn_ambient_temperature 293
_diffrn_radiation_wavelength 1.5418
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'X-ray tube'
_diffrn_radiation_monochromator 'graphite'
_diffrn_radiation_detector ?
_diffrn_measurement_device
'Philips PW1100/20 diffractometer'
_diffrn_measurement_method \q/2\q
_diffrn_standards_number 3
_diffrn_standards_interval_time 120
_diffrn_standards_decay_% 0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 2 4 1 9 1 3 0 10
loop_
_diffrn_attenuator_code
_diffrn_attenuator_scale
1 16.976
_diffrn_reflns_number 1592
_diffrn_reflns_av_R_equivalents 0
_diffrn_reflns_av_sigmaI/netI .027
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 0
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_theta_min 3.71
_diffrn_reflns_theta_max 61.97
_diffrn_reflns_reduction_process ?
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 72 .017 .009
International_Tables_Vol_IV_Table_2.2B
H 0 100 0 0
International_Tables_Vol_IV_Table_2.2B
O 0 12 .047 .032
International_Tables_Vol_IV_Table_2.2B
N 0 4 .029 .018
International_Tables_Vol_IV_Table_2.2B
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
O1 .4154(4) .5699(1) .3026(1) .060(1) Uani ? ?
C2 .5630(5) .5087(2) .3246(1) .060(2) Uani ? ?
C3 .5350(5) .4920(2) .3997(1) .048(1) Uani ? ?
N4 .3570(3) .5558(1) .4167(1) .039(1) Uani ? ?
C5 .3000(5) .6122(2) .3581(1) .045(1) Uani ? ?
O21 .6958(5) .4738(2) .2874(1) .090(2) Uani ? ?
C31 .4869(6) .3929(2) .4143(2) .059(2) Uani ? ?
C32 .2552(7) .3558(2) .3953(2) .073(2) Uani ? ?
C321 .209(1) .3542(4) .3211(3) .111(4) Uani ? ?
C322 .230(1) .2626(3) .4264(3) .149(5) Uani ? ?
C41 .2034(4) .5476(2) .4682(1) .041(1) Uani ? ?
# . . . . . . . . . . . . . . . . . . . . . . . data omitted for brevity
H321C .04(1) .318(3) .320(2) .14000 Uiso ? ?
H322A .25(1) .272(4) .475(3) .19000 Uiso ? ?
H322B .34976 .22118 .40954 .19000 Uiso calc C322
H322C .08(1) .234(4) .397(3) .19000 Uiso ? ?
H412 -.007(6) .447(2) .552(2) .08000 Uiso ? ?
H513B .115(7) .757(3) .426(2) .09000 Uiso ? ?
H513C .329(6) .817(2) .430(2) .09000 Uiso ? ?
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 .071(1) .076(1) .0342(9) .008(1) .0051(9) -.0030(9)
C2 .060(2) .072(2) .047(1) .002(2) .013(1) -.009(1)
C3 .038(1) .060(2) .044(1) .007(1) .001(1) -.005(1)
N4 .037(1) .048(1) .0325(9) .0025(9) .0011(9) -.0011(9)
C5 .043(1) .060(1) .032(1) .001(1) -.001(1) .001(1)
# . . . . . . . . . . . . . . . . . . . . . . . data omitted for brevity
O21 .094(2) .109(2) .068(1) .023(2) .038(1) -.010(1)
C51 .048(2) .059(2) .049(1) .002(1) -.000(1) .007(1)
C511 .048(2) .071(2) .097(3) -.008(2) -.003(2) .010(2)
C512 .078(2) .083(2) .075(2) .009(2) -.005(2) .033(2)
C513 .074(2) .055(2) .075(2) .004(2) .001(2) -.010(2)
_refine_special_details
sfls:_F_calc_weight_full_matrix
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_weighting_scheme
'calc w=1/(\s^2^(F)+0.0004F^2^)'
_refine_ls_hydrogen_treatment
'refxyz except H332B noref'
_refine_ls_extinction_method Zachariasen
_refine_ls_extinction_coef 3514(42)
_refine_ls_extinction_expression
'equ(22) p292 "Crystallographic Computing" (1970)'
_refine_ls_abs_structure_details
;
The absolute configuration was assigned to agree
with the known chirality at C3 arising from its
precursor l-leucine.
;
_refine_ls_abs_structure_Flack 0
_refine_ls_number_reflns 1408
_refine_ls_number_parameters 272
_refine_ls_number_restraints 0
_refine_ls_number_constraints 0
_refine_ls_R_factor_all .038
_refine_ls_R_factor_obs .034
_refine_ls_wR_factor_all .044
_refine_ls_wR_factor_obs .042
_refine_ls_goodness_of_fit_all 1.462
_refine_ls_goodness_of_fit_obs 1.515
_refine_ls_shift/esd_max .164
_refine_ls_shift/esd_mean .044
_refine_diff_density_min -.108
_refine_diff_density_max .131
_geom_special_details ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.342(4) . . yes
O1 C5 1.439(3) . . yes
C2 C3 1.512(4) . . yes
C2 O21 1.199(4) . . yes
C3 N4 1.465(3) . . yes
C3 C31 1.537(4) . . yes
C3 H3 1.00(3) . . ?
N4 C5 1.472(3) . . yes
N4 C41 1.374(3) . . yes
C5 C51 1.528(4) . . yes
C5 H5 1.00(3) . . ?
C31 C32 1.535(5) . . yes
C31 H31A .95(3) . . ?
C31 H31B .96(3) . . ?
C32 C321 1.490(7) . . yes
C32 C322 1.531(6) . . yes
C32 H32 1.10(4) . . ?
# . . . . . . . . . . . . . . . . . . . . . . . data omitted for brevity
C513 H513C 1.02(4) . . ?
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C5 111.6(2) . . . yes
O1 C2 C3 110.9(2) . . . yes
O1 C2 O21 122.2(3) . . . yes
C3 C2 O21 127.0(3) . . . yes
C2 C3 N4 101.3(2) . . . yes
C2 C3 C31 111.3(2) . . . yes
C2 C3 H3 107(1) . . . ?
N4 C3 C31 116.7(2) . . . yes
N4 C3 H3 110(1) . . . ?
C31 C3 H3 110(1) . . . ?
C3 N4 C5 111.2(2) . . . yes
C3 N4 C41 126.4(2) . . . yes
C5 N4 C41 118.6(2) . . . yes
# . . . . . . . . . . . . . . . . . . . . . . . data omitted for brevity
H513B C513 H513C 104(1) . . . ?
_reflns_limit_h_min 0
_reflns_limit_h_max 6
_reflns_limit_k_min 0
_reflns_limit_k_max 17
_reflns_limit_l_min 0
_reflns_limit_l_max 22
_reflns_number_total 1592
_reflns_number_observed 1408
_reflns_observed_criterion
refl_observed_if_F_>_6.0_sigma(F)
_reflns_d_resolution_high 0.8733
_reflns_d_resolution_low 11.9202
loop_
_reflns_scale_group_code
_reflns_scale_meas_F 1 .960926
loop_
_refln_index_h
_refln_index_k
_refln_index_l
_refln_F_meas
_refln_F_calc
_refln_F_sigma
_refln_observed_status
_refln_scale_group_code
? ? ? ? ? ? ? ?
#------------------------
_publ_requested_journal
'Acta Crystallographica C'
_publ_contact_author
;
Dr Anthony C. Willis
Research School of Chemistry
Australian National University
GPO Box 4
Canberra, A.C.T.
Australia 2601
;
_publ_contact_letter
;
Please consider this CIF submission for
publication as a Short Format Paper in Acta
Crystallographica C. The figure and structure
factor listings will be sent by normal mail.
;
_publ_requested_coeditor_name 'Prof. S.R.Hall'
_publ_contact_author_phone '616 249 4109'
_publ_contact_author_fax '616 249 0750'
_publ_contact_author_email willis@RSC3.anu.oz.au
loop_
_publ_author_name
_publ_author_address
'Willis, Anthony C.'
; Research School of Chemistry
Australian National University
GPO Box 4
Canberra, A.C.T.
Australia 2601
;
'Beckwith, Athelstan L.J.'
; Research School of Chemistry
Australian National University
GPO Box 4
Canberra, A.C.T.
Australia 2601
;
'Tozer, Matthew J.'
; Research School of Chemistry
Australian National University
GPO Box 4
Canberra, A.C.T.
Australia 2601
;
_publ_section_title
;
trans-3-Benzoyl-2-(tert-butyl)-4-(isobutyl)-
1,3-oxazolidin-5-one
;
_publ_section_abstract
;
The oxazolidinone ring is a shallow envelope
conformation with the tert-butyl and isobutyl groups
occupying trans-positions with respect to the ring.
The angles at the N atom sum to 356.2\%, indicating a
very small degree of pyramidalization at this atom.
This is consistent with electron delocalization between
the N atom and the carbonyl centre [N-C=O = 1.374(3)\%A].
;
_publ_section_experimental
;
The \q scan width was (1.0+0.14tan\q)\% with a \q scan
rate of 1.2\% per min. and background counts for 5s on
each side of every scan. The absolute configuration has
been assigned to agree with the known chirality at C3
arising from its precursor l-leucine. Refinement was by
full-matrix least-squares methods.
;
_publ_section_comment
;
The structure of the title compound was undertaken
to establish whether an isobutyl group would be formed
cis or trans to the tert-butyl group as part of a
study of diastereoselectivities of free radical
reactions. Details of the synthetic work will be
published elsewhere (Beckwith, Chai & Tozer, 1991).
The X-ray analysis shows that the tert-butyl and
isobutyl groups are trans, as expected from nmr
evidence. The oxazolidinone ring is in an envelope
conformation with C5 the out-of-plane atom. The angle
between the least-squares plane through atoms O1, C2,
C3 and N4 and the plane of N4, C5 and O1 is 10.9(2)\%.
Intra-annular torsion angles (starting with C5-O1-C2-C3
and proceeding around the ring) are 9.5, -2.3, -5.4,
10.7 and -12.3(3)\%. A search of the January 1990
Version of the Cambridge Structure Database (Allen,
Kennard & Taylor, 1983) revealed three structure
determinations with 1,3-oxazolidin-5-one fragments
(Seebach, Boes, Naef & Schweizer 1983, Karady, Amato
& Weinstock 1984, Weber, Aeschimann, Maetzke & Seebach,
1986). Bond lengths and angles in these compounds are
comparable with those in the present study; the
magnitudes of their respective maximum intra-annular
torsion angle are 10.2, 1.9 and 10.2\%. Diagrams and
most calculations were performed with the Xtal3.0
package (Hall & Stewart, 1990), as was the generation
of the Crystallographic Information File used for the
submission of this paper.
;
_publ_section_references
;
Allen, F.H., Kennard, O. and Taylor, R. (1983).
Accounts Chem. Res., 16, 146-153.
Beckwith, A.L.J., Chai, C.L.L. & Tozer, M.J. (1991).
Manuscript in preparation.
Hall, S.R. and Stewart, J.M. (1990). Eds. Xtal3.0
Reference Manual. University of Western Australia
and University of Maryland.
Karady, S., Amato, J.S. & Weinstock, L.M. (1984).
Tetrahedron Lett., 25, 4337-4340.
McLaughlin, G.M. (1983). PWREDU. Program for data
reduction for Philips PW1100/20 diffractometer.
Australian National Univ., Canberra.
Seebach, D., Boes,M., Naef, W.B. & Schweizer, W.B.
(1983). J Am. Chem. Soc., 105,5390-5398.
Sheldrick, G.M. (1976). SHELX76. Program for crystal
structure determination. Univ. of Cambridge, England.
Sheldrick, G.M. (1985). SHELXS86. Program for the
solution of crystal structures. Univ. of Gottingen,
Federal Republic of Germany.
Weber, T., Aeschimann, R., Maetzke, T. & Seebach, D.
(1986). Helv. Chim. Acta, 69,1365-1377.
;
_publ_section_figure_captions
;
View of C~18~H~25~NO~3~ showing the labelling of the
non-H atoms. Thermal ellipsoids are shown at 50%
probability levels; H atoms are drawn as small circles
of arbitrary radius.
;
Copyright © 1991 International Union of Crystallography
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