#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008927.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_2008927 loop_ _publ_author_name 'Kabak, Mehmet' 'Elerman, Yal\;cin' 'G\"uner, Vildan' 'Yildirir, S\"uleyman' 'Durlu, Tahsin Nuri' _publ_section_title ; 3,3-Dichloro-1,4-diphenylazetidin-2-one ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1511 _journal_page_last 1512 _journal_paper_doi 10.1107/S0108270199006095 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C15 H11 Cl2 N O' _chemical_formula_sum 'C15 H11 Cl2 N O' _chemical_formula_weight 292.16 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _audit_creation_method 'by teXsan for Windows v1.0' _cell_angle_alpha 90 _cell_angle_beta 91.989(8) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 19.305(2) _cell_length_b 5.9580(10) _cell_length_c 23.847(2) _cell_measurement_reflns_used 22 _cell_measurement_temperature 293.2 _cell_measurement_theta_max 14.3 _cell_measurement_theta_min 10.1 _cell_volume 2741.2(6) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994) ; _computing_data_reduction 'TEXSAN for Windows (Molecular Structure Corporation, 1997)' _computing_publication_material 'TEXSAN for Windows' _computing_structure_refinement 'TEXSAN for Windows' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 293.2 _diffrn_measurement_device 'Rigaku AFC-7S' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.081 _diffrn_reflns_av_sigmaI/netI 0.132 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 4488 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 30.01 _diffrn_reflns_theta_min 0.86 _diffrn_standards_decay_% 0.11 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.463 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_type '\y scans (North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_meas ? _exptl_crystal_description hexagonal _exptl_crystal_F_000 1200.00 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.31 _refine_diff_density_min -0.55 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.949 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 172 _refine_ls_number_reflns 1764 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.057 _refine_ls_R_factor_gt 0.057 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef F _refine_ls_weighting_details unit _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all 0.057 _refine_ls_wR_factor_ref 0.057 _reflns_number_gt 1764 _reflns_number_total 4360 _reflns_threshold_expression I>3\s(I) _cod_data_source_file ka1319.cif _cod_data_source_block vd1 _cod_depositor_comments ; Moving '_atom_site_adp_type' tag from the 6th to the 8th loop position in '_atom_site' loop in accordance to data. Antanas Vaitkus, 2015-03-24 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 2741.0(5) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2008927 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, +y,1/2-z' ' -x, -y, -z' ' +x, -y,1/2+z' '1/2+x,1/2+y, +z' 1/2-x,1/2+y,1/2-z '1/2-x,1/2-y, -z' 1/2+x,1/2-y,1/2+z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_adp_type _atom_site_occupancy Cl1 0.49709(7) 0.4554(3) 0.17034(7) 0.0677(5) d ? Uani 1.000 Cl2 0.50662(7) 0.2192(3) 0.06547(7) 0.0773(5) d ? Uani 1.000 O1 0.3939(2) 0.6580(7) 0.0623(2) 0.0690(10) d ? Uani 1.000 N1 0.3441(2) 0.3268(7) 0.0965(2) 0.0390(10) d ? Uani 1.000 C1 0.2393(2) 0.4799(9) 0.0528(2) 0.0470(10) d ? Uani 1.000 C2 0.1688(3) 0.4540(10) 0.0382(2) 0.057(2) d ? Uani 1.000 C3 0.1341(2) 0.2670(10) 0.0538(2) 0.061(2) d ? Uani 1.000 C4 0.1675(2) 0.0970(10) 0.0818(2) 0.055(2) d ? Uani 1.000 C5 0.2380(2) 0.1178(9) 0.0966(2) 0.0470(10) d ? Uani 1.000 C6 0.2727(2) 0.3091(9) 0.0813(2) 0.0390(10) d ? Uani 1.000 C7 0.3938(2) 0.4809(9) 0.0850(2) 0.0460(10) d ? Uani 1.000 C8 0.4498(2) 0.3326(9) 0.1141(2) 0.0470(10) d ? Uani 1.000 C9 0.3887(2) 0.1715(8) 0.1291(2) 0.0410(10) d ? Uani 1.000 C10 0.3715(2) 0.1458(8) 0.1899(2) 0.0430(10) d ? Uani 1.000 C11 0.3935(3) -0.0430(10) 0.2193(3) 0.069(2) d ? Uani 1.000 C12 0.3786(4) -0.0660(10) 0.2752(3) 0.087(3) d ? Uani 1.000 C13 0.3412(3) 0.0950(10) 0.3016(3) 0.076(2) d ? Uani 1.000 C14 0.3184(3) 0.2790(10) 0.2728(2) 0.070(2) d ? Uani 1.000 C15 0.3335(3) 0.3060(10) 0.2169(2) 0.054(2) d ? Uani 1.000 H1 0.2645 0.6153 0.0429 0.058 c ? Uiso 1.000 H2 0.1442 0.5713 0.0169 0.069 c ? Uiso 1.000 H3 0.0852 0.2554 0.0450 0.073 c ? Uiso 1.000 H4 0.1422 -0.0388 0.0916 0.066 c ? Uiso 1.000 H5 0.2625 -0.0005 0.1176 0.058 c ? Uiso 1.000 H9 0.3950 0.0389 0.1097 0.053 c ? Uiso 1.000 H11 0.4198 -0.1593 0.1999 0.082 c ? Uiso 1.000 H12 0.3947 -0.1977 0.2965 0.102 c ? Uiso 1.000 H13 0.3305 0.0769 0.3408 0.091 c ? Uiso 1.000 H14 0.2917 0.3945 0.2920 0.085 c ? Uiso 1.000 H15 0.3169 0.4378 0.1962 0.067 c ? Uiso 1.000 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 Cl1 0.0435(6) 0.0810(10) 0.0790(10) -0.0093(7) -0.0038(6) -0.0218(9) Cl2 0.0437(7) 0.1010(10) 0.0890(10) 0.0003(8) 0.0270(7) -0.0300(10) O1 0.061(2) 0.063(3) 0.083(3) -0.014(2) 0.006(2) 0.012(2) N1 0.033(2) 0.040(2) 0.045(2) -0.003(2) 0.004(2) 0.005(2) C1 0.044(2) 0.054(3) 0.042(3) 0.006(2) 0.008(2) -0.001(2) C2 0.046(3) 0.080(4) 0.045(3) 0.019(3) 0.001(2) -0.002(3) C3 0.034(2) 0.092(5) 0.056(3) 0.003(3) 0.001(2) -0.008(3) C4 0.040(2) 0.068(4) 0.056(3) -0.012(3) 0.005(2) -0.004(3) C5 0.038(2) 0.052(3) 0.049(3) -0.004(2) 0.001(2) 0.002(3) C6 0.034(2) 0.051(3) 0.034(2) 0.000(2) 0.006(2) 0.001(2) C7 0.046(3) 0.041(3) 0.052(3) -0.006(2) 0.013(2) -0.003(3) C8 0.035(2) 0.049(3) 0.058(3) -0.001(2) 0.009(2) -0.014(3) C9 0.033(2) 0.036(3) 0.054(3) 0.003(2) 0.006(2) -0.004(2) C10 0.035(2) 0.042(3) 0.050(3) 0.000(2) 0.000(2) 0.000(2) C11 0.071(4) 0.057(4) 0.078(4) 0.017(3) 0.004(3) 0.012(3) C12 0.093(5) 0.091(6) 0.075(5) 0.003(4) -0.008(4) 0.037(4) C13 0.072(4) 0.108(6) 0.049(3) -0.023(4) 0.002(3) 0.015(4) C14 0.064(3) 0.094(5) 0.051(3) 0.004(4) 0.011(3) -0.003(4) C15 0.054(3) 0.058(4) 0.052(3) 0.013(3) 0.004(2) 0.002(3) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.002 0.002 'International Tables (1992, Vol. C, Table 6.1.1.2)' H 0.000 0.000 'International Tables (1992, Vol. C, Table 6.1.1.2)' N 0.004 0.003 'International Tables (1992, Vol. C, Table 6.1.1.2)' O 0.008 0.006 'International Tables (1992, Vol. C, Table 6.1.1.2)' Cl 0.132 0.159 'International Tables (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -1 -1 1 -1 -4 3 -1 3 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 C6 N1 C7 133.2(4) y C6 N1 C9 129.4(4) y C7 N1 C9 97.4(3) y C2 C1 C6 118.5(5) y C2 C1 H1 121.2 no C6 C1 H1 120.2 no C1 C2 C3 120.4(5) ? C1 C2 H2 120.1 no C3 C2 H2 119.5 no C2 C3 C4 121.0(4) ? C2 C3 H3 119.3 no C4 C3 H3 119.7 no C3 C4 C5 119.7(5) ? C3 C4 H4 120.0 no C5 C4 H4 120.4 no C4 C5 C6 119.1(5) ? C4 C5 H5 120.9 no C6 C5 H5 120.1 no N1 C6 C1 120.5(4) y N1 C6 C5 118.2(4) y C1 C6 C5 121.3(4) y O1 C7 N1 134.8(5) y O1 C7 C8 134.6(5) y N1 C7 C8 90.6(4) y Cl1 C8 Cl2 110.1(2) y Cl1 C8 C7 116.3(3) y Cl1 C8 C9 117.1(3) y Cl2 C8 C7 111.5(3) y Cl2 C8 C9 114.0(3) y C7 C8 C9 86.1(3) y N1 C9 C8 85.7(3) y N1 C9 C10 115.5(3) y N1 C9 H9 110.9 no C8 C9 C10 118.3(4) y C8 C9 H9 107.1 no C10 C9 H9 115.6 no C9 C10 C11 119.8(5) y C9 C10 C15 121.3(4) y C11 C10 C15 118.9(5) y C10 C11 C12 120.1(6) ? C10 C11 H11 119.3 no C12 C11 H11 120.6 no C11 C12 C13 120.4(6) ? C11 C12 H12 120.5 no C13 C12 H12 119.0 no C12 C13 C14 119.9(6) ? C12 C13 H13 120.1 no C14 C13 H13 120.0 no C13 C14 C15 120.3(6) ? C13 C14 H14 119.7 no C15 C14 H14 120.0 no C10 C15 C14 120.3(5) ? C10 C15 H15 119.5 no C14 C15 H15 120.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C8 . . 1.756(5) y Cl2 C8 . . 1.759(4) y O1 C7 . . 1.186(6) y N1 C6 . . 1.417(5) y N1 C7 . . 1.362(6) y N1 C9 . . 1.469(5) y C1 C2 . . 1.402(6) y C1 C6 . . 1.372(6) y C1 H1 . . 0.98 no C2 C3 . . 1.358(8) y C2 H2 . . 0.98 no C3 C4 . . 1.366(8) y C3 H3 . . 0.96 no C4 C5 . . 1.400(6) y C4 H4 . . 0.97 no C5 C6 . . 1.377(6) y C5 H5 . . 0.98 no C7 C8 . . 1.543(7) y C8 C9 . . 1.571(6) y C9 C10 . . 1.505(6) y C9 H9 . . 0.93 no C10 C11 . . 1.383(7) y C10 C15 . . 1.378(6) y C11 C12 . . 1.380(8) y C11 H11 . . 0.98 no C12 C13 . . 1.368(9) y C12 H12 . . 0.98 no C13 C14 . . 1.361(9) y C13 H13 . . 0.97 no C14 C15 . . 1.384(7) y C14 H14 . . 0.98 no C15 H15 . . 0.98 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl1 H11 2.8401 1_565 no Cl1 H12 3.0236 2_665 no Cl2 H4 3.0339 5 no Cl2 C2 3.586(5) 5_545 no O1 H9 2.5351 1_565 no O1 H2 2.5710 7_565 no O1 C9 3.453(6) 1_565 no O1 C2 3.513(7) 7_565 no C1 H13 2.9705 6 no C2 H13 2.9770 6 no C2 C6 3.476(6) 7 no C5 H14 3.0439 6_545 no H1 H1 2.6450 7_565 no H5 H14 2.5082 6_545 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 Cl1 C8 C7 O1 57.5(7) no Cl1 C8 C7 N1 -121.9(3) no Cl1 C8 C9 N1 120.9(3) no Cl1 C8 C9 C10 4.2(5) no Cl2 C8 C7 O1 -69.8(7) no Cl2 C8 C7 N1 110.7(3) no Cl2 C8 C9 N1 -108.6(3) no Cl2 C8 C9 C10 134.7(4) no O1 C7 N1 C6 6.0(10) no O1 C7 N1 C9 -175.6(6) no O1 C7 C8 C9 175.9(6) no N1 C6 C1 C2 179.3(4) no N1 C6 C5 C4 -179.7(4) no N1 C7 C8 C9 -3.5(3) no N1 C9 C8 C7 3.3(3) no N1 C9 C10 C11 158.9(4) no N1 C9 C10 C15 -20.4(6) no C1 C2 C3 C4 -2.9(8) no C1 C6 N1 C7 -6.1(7) no C1 C6 N1 C9 176.5(4) no C1 C6 C5 C4 1.0(7) no C2 C1 C6 C5 -1.4(7) no C2 C3 C4 C5 2.5(8) no C3 C2 C1 C6 2.3(7) no C3 C4 C5 C6 -1.5(8) no C5 C6 N1 C7 174.6(5) no C5 C6 N1 C9 -2.8(7) no C6 N1 C7 C8 -174.2(4) no C6 N1 C9 C8 174.4(4) no C6 N1 C9 C10 -66.3(6) no C7 N1 C9 C8 -3.7(4) no C7 N1 C9 C10 115.6(4) no C7 C8 C9 C10 -113.4(4) no C8 C7 N1 C9 3.8(4) no C8 C9 C10 C11 -101.9(5) no C8 C9 C10 C15 78.8(6) no C9 C10 C11 C12 179.3(5) no C9 C10 C15 C14 -179.8(5) no C10 C11 C12 C13 1.0(10) no C10 C15 C14 C13 0.1(9) no C11 C10 C15 C14 0.9(8) no C11 C12 C13 C14 .0(10) no C12 C11 C10 C15 -1.4(8) no C12 C13 C14 C15 -1.0(10) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2278128 2 PubChem 12246286