#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005105.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2005105 loop_ _publ_author_name 'Ercan, F.' '\"Ulk\"u, D.' 'G\"uner, V.' _publ_section_title ; 3,3-Dichloro-4-(p-methoxyphenyl)-1-phenyl-2-azetidinone ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1779 _journal_page_last 1780 _journal_paper_doi 10.1107/S0108270196002119 _journal_volume 52 _journal_year 1996 _chemical_formula_iupac 'C16 H13 Cl2 N O2' _chemical_formula_moiety 'C16 H13 Cl2 N O2' _chemical_formula_sum 'C16 H13 Cl2 N O2' _chemical_formula_weight 322.19 _chemical_name_systematic ; 3,3-dichlor-4-(p-metoxyphenyl)-1-phenyl-2-azetidinone ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 93.650(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.739(3) _cell_length_b 14.237(2) _cell_length_c 18.644(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 16 _cell_measurement_theta_min 10 _cell_volume 1520.2(8) _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1993)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics 'ORTEP (Johnson, 1965) in MolEN' _computing_publication_material MolEN _computing_structure_refinement 'MolEN LSFM' _computing_structure_solution 'MolEN SIMPEL' _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 3089 _diffrn_reflns_theta_max 25.0 _diffrn_standards_decay_% 1.1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.43 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_type 'empirical via \y scans (North, Phillips & Mathews, 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.41 _exptl_crystal_density_method none _exptl_crystal_description needle _exptl_crystal_F_000 660 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _refine_diff_density_max .20 _refine_diff_density_min -.24 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 0.64 _refine_ls_hydrogen_treatment 'H atoms refined with U(H) = 1.3U~eq~(C)' _refine_ls_number_parameters 229 _refine_ls_number_reflns 1950 _refine_ls_R_factor_obs .042 _refine_ls_shift/esd_max .00 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = (84.32/F)^2^ if F>=84.32, otherwise w = 1.0' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .040 _reflns_number_observed 1950 _reflns_number_total 2666 _reflns_observed_criterion I>2\s(I) _[local]_cod_data_source_file cf1057.cif _[local]_cod_data_source_block azetidin _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = (84.32/F)^2^ if F>=84.32, otherwise w = 1.0' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = (84.32/F)^2^ if F>=84.32, otherwise w = 1.0'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2005105 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z 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 _atom_site_aniso_type_symbol Cl1 0.0566(4) 0.0586(5) 0.0779(5) 0.0012(4) 0.0150(4) 0.0031(5) Cl Cl2 0.0643(5) 0.0606(5) 0.1089(7) 0.0101(4) 0.0175(5) -0.0289(5) Cl O1 0.0490(10) 0.082(2) 0.084(2) -0.0140(10) -0.0180(10) -0.005(2) O O2 0.0740(10) 0.0670(10) 0.0520(10) 0.0060(10) -0.0020(10) -0.0080(10) O C2 0.046(2) 0.055(2) 0.060(2) -0.003(2) 0.004(2) -0.009(2) C C3 0.041(2) 0.045(2) 0.064(2) 0.0040(10) 0.0040(10) -0.008(2) C C4 0.0310(10) 0.053(2) 0.055(2) 0.0050(10) 0.0020(10) -0.004(2) C N1 0.0420(10) 0.0540(10) 0.0520(10) -0.0040(10) -0.0050(10) -0.0050(10) N C5 0.0320(10) 0.044(2) 0.054(2) 0.0030(10) 0.0010(10) 0.0010(10) C C6 0.0340(10) 0.052(2) 0.062(2) 0.0100(10) 0.0010(10) 0.002(2) C C7 0.0380(10) 0.063(2) 0.055(2) 0.003(2) -0.0100(10) 0.003(2) C C8 0.050(2) 0.043(2) 0.044(2) -0.0050(10) 0.0030(10) 0.0040(10) C C9 0.041(2) 0.043(2) 0.060(2) 0.0070(10) 0.0030(10) 0.0000(10) C C10 0.0320(10) 0.052(2) 0.058(2) 0.0050(10) -0.0050(10) -0.002(2) C C11 0.043(2) 0.057(2) 0.050(2) 0.0000(10) 0.0010(10) -0.007(2) C C12 0.058(2) 0.061(2) 0.073(2) -0.001(2) -0.014(2) -0.005(2) C C13 0.078(2) 0.069(2) 0.076(2) 0.008(2) -0.012(2) 0.007(2) C C14 0.083(3) 0.070(2) 0.079(2) -0.004(2) 0.000(2) 0.018(2) C C15 0.069(2) 0.080(2) 0.086(3) -0.023(2) -0.004(2) 0.011(2) C C16 0.055(2) 0.077(2) 0.065(2) -0.013(2) -0.008(2) 0.013(2) C C17 0.105(3) 0.056(2) 0.061(2) 0.003(2) 0.015(2) -0.009(2) C loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv _atom_site_thermal_displace_type _atom_site_type_symbol Cl1 .8047(2) .26871(6) .28527(5) 5.04(2) Beq Cl Cl2 1.0826(2) .20606(7) .17131(6) 6.11(2) Beq Cl O1 .6125(4) .3435(2) .11840(10) 5.73(6) Beq O O2 1.2007(4) .5869(2) .47830(10) 5.09(5) Beq O C2 .7945(5) .3590(2) .1530(2) 4.22(7) Beq C C3 .9478(5) .3037(2) .2088(2) 3.95(7) Beq C C4 1.1051(5) .3929(2) .2147(2) 3.67(6) Beq C N1 .9443(5) .4328(2) .15720(10) 3.92(6) Beq N C5 1.1239(5) .4469(2) .2832(2) 3.40(6) Beq C C6 1.3194(5) .4356(2) .3310(2) 3.91(7) Beq C C7 1.3401(5) .4825(2) .3948(2) 4.15(7) Beq C C8 1.1660(5) .5431(2) .4140(2) 3.62(6) Beq C C9 .9693(5) .5562(2) .3675(2) 3.80(7) Beq C C10 .9509(5) .5081(2) .3030(2) 3.79(6) Beq C C11 .9597(5) .5165(2) .1182(2) 3.96(7) Beq C C12 .7902(6) .5397(3) .0646(2) 5.09(8) Beq C C13 .8094(7) .6211(3) .0255(2) 5.93(9) Beq C C14 .9951(7) .6804(3) .0395(2) 6.10(10) Beq C C15 1.1605(7) .6574(3) .0928(2) 6.20(10) Beq C C16 1.1456(6) .5770(3) .1318(2) 5.22(8) Beq C C17 1.0263(8) .6514(3) .4980(2) 5.81(9) Beq C H171 1.079(6) .673(2) .543(2) 7.2 Biso H H172 1.031(6) .711(2) .460(2) 7.2 Biso H H173 .862(6) .614(2) .501(2) 7.2 Biso H H6 1.429(5) .395(2) .317(2) 5.2 Biso H H7 1.469(5) .474(2) .424(2) 5.1 Biso H H9 .857(5) .597(2) .378(2) 5.2 Biso H H10 .808(5) .520(2) .270(2) 5.1 Biso H H12 .668(5) .496(2) .0560(10) 4.0 Biso H H13 .705(9) .642(4) -.010(3) 7.0 Biso H H14 .996(6) .738(3) .015(2) 8.1 Biso H H15 1.257(6) .700(2) .105(2) 6.9 Biso H H16 1.238(5) .560(2) .167(2) 5.2 Biso H H4 1.249(4) .385(2) .1980(10) 4.0(6) Biso H loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C8 O2 C17 117.4(3) yes O1 C2 C3 134.8(3) yes O1 C2 N1 133.9(3) yes C3 C2 N1 91.3(2) yes Cl1 C3 Cl2 109.7(2) yes Cl1 C3 C2 114.6(2) yes Cl1 C3 C4 118.1(2) yes Cl2 C3 C2 112.6(2) yes Cl2 C3 C4 113.9(2) yes C2 C3 C4 86.3(2) yes C3 C4 N1 85.9(2) yes C3 C4 C5 119.5(3) yes N1 C4 C5 115.5(3) yes C2 N1 C4 96.3(3) yes C2 N1 C11 133.5(3) yes C4 N1 C11 130.1(3) yes C4 C5 C6 120.0(3) no C4 C5 C10 122.6(3) no C6 C5 C10 117.4(3) no C5 C6 C7 121.5(3) no C6 C7 C8 120.5(3) no O2 C8 C7 116.6(3) no O2 C8 C9 123.8(3) no C7 C8 C9 119.5(3) no C8 C9 C10 119.3(3) no C5 C10 C9 121.8(3) no N1 C11 C12 120.7(3) no N1 C11 C16 120.5(3) no C12 C11 C16 118.8(3) no C11 C12 C13 120.3(4) no C12 C13 C14 120.3(4) no C13 C14 C15 119.1(4) no C14 C15 C16 121.6(4) no C11 C16 C15 120.0(4) no C5 C6 H6 116.(2) no C7 C6 H6 123.(2) no C6 C7 H7 119.(2) no C8 C7 H7 121.(2) no C8 C9 H9 121.(2) no C10 C9 H9 120.(2) no C5 C10 H10 121.(2) no C9 C10 H10 118.(2) no C11 C12 H12 117.(2) no C13 C12 H12 123.(2) no C12 C13 H13 126.(4) no C14 C13 H13 114.(4) no C13 C14 H14 118.(3) no C15 C14 H14 122.(3) no C14 C15 H15 116.(3) no C16 C15 H15 122.(3) no C11 C16 H16 114.(2) no C15 C16 H16 126.(2) no O2 C17 H171 105.(3) no O2 C17 H172 106.(2) no O2 C17 H173 109.(2) no H171 C17 H172 108.(3) no H171 C17 H173 110.(3) no H172 C17 H173 117.(3) no C3 C4 H4 114.(2) no N1 C4 H4 110.(2) no C5 C4 H4 110.(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C3 1.762(3) yes Cl2 C3 1.757(3) yes O1 C2 1.213(4) yes O2 C8 1.355(4) yes O2 C17 1.423(5) yes C2 C3 1.536(5) yes C2 N1 1.357(4) yes C3 C4 1.558(4) yes C4 N1 1.482(4) yes C4 C5 1.487(4) yes N1 C11 1.403(4) yes C5 C6 1.398(4) no C5 C10 1.390(4) no C6 C7 1.362(5) no C6 H6 0.90(3) no C7 C8 1.383(4) no C7 H7 0.90(3) no C8 C9 1.392(4) no C9 C10 1.381(5) no C9 H9 0.90(3) no C10 H10 1.01(3) no C11 C12 1.389(5) no C11 C16 1.382(5) no C12 C13 1.377(6) no C12 H12 0.94(3) no C13 C14 1.372(6) no C13 H13 0.91(6) no C14 C15 1.369(6) no C14 H14 0.94(4) no C15 C16 1.363(6) no C15 H15 0.84(4) no C16 H16 0.85(3) no C17 H171 0.93(4) no C17 H172 1.11(4) no C17 H173 1.09(4) no C4 H4 0.91(3) no 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_publ_flag C17 O2 C8 C7 178.3(3) yes C17 O2 C8 C9 -1.3(4) no O1 C2 C3 Cl1 -57.8(5) no O1 C2 C3 Cl2 68.5(5) no O1 C2 C3 C4 -177.1(4) no N1 C2 C3 Cl1 122.5(2) no N1 C2 C3 Cl2 -111.2(2) no N1 C2 C3 C4 3.2(2) no O1 C2 N1 C4 176.9(4) no O1 C2 N1 C11 -7.3(6) no C3 C2 N1 C4 -3.4(2) yes C3 C2 N1 C11 172.4(3) yes Cl1 C3 C4 N1 -119.0(2) no Cl1 C3 C4 C5 -1.9(4) no Cl2 C3 C4 N1 110.1(2) no Cl2 C3 C4 C5 -132.8(3) no C2 C3 C4 N1 -3.0(2) no C2 C3 C4 C5 114.2(3) yes C3 C4 N1 C2 3.4(2) no C3 C4 N1 C11 -172.6(3) no C5 C4 N1 C2 -117.5(3) no C5 C4 N1 C11 66.6(4) no C3 C4 C5 C6 101.0(3) yes C3 C4 C5 C10 -77.8(4) no N1 C4 C5 C6 -158.7(3) no N1 C4 C5 C10 21.6(4) no C2 N1 C11 C12 3.9(5) yes C2 N1 C11 C16 -175.3(3) no C4 N1 C11 C12 178.4(3) no C4 N1 C11 C16 -0.8(5) no C4 C5 C6 C7 -178.7(3) no C10 C5 C6 C7 -0.1(5) no C4 C5 C10 C9 178.7(3) no C6 C5 C10 C9 0.1(4) no C5 C6 C7 C8 0.1(5) no C6 C7 C8 O2 180.0(3) no C6 C7 C8 C9 -0.5(5) no O2 C8 C9 C10 179.9(3) no C7 C8 C9 C10 0.4(5) no C8 C9 C10 C5 -0.1(5) no N1 C11 C12 C13 -178.6(3) no C16 C11 C12 C13 0.6(5) no N1 C11 C16 C15 179.0(3) no C12 C11 C16 C15 -0.2(5) no C11 C12 C13 C14 -0.6(6) no C12 C13 C14 C15 0.1(6) no C13 C14 C15 C16 0.3(6) no