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. ;
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