#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/11/2101102.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_2101102 loop_ _publ_author_name 'Ciechanowicz-Rutkowska, M.' 'Kie\'c-Kononowicz, K.' 'Howard, S. T.' 'Lieberman, H.' 'Hursthouse, M. B.' _publ_section_title ; Molecular and electronic structures of two (anticonvulsant) diphenylhydantoin derivatives ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 86 _journal_page_last 96 _journal_paper_doi 10.1107/S0108768193007943 _journal_volume 50 _journal_year 1994 _chemical_formula_sum 'C24 H18 Cl2 N2 O4' _chemical_formula_weight 469.323 _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 94.281(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.0392(7) _cell_length_b 9.7237(6) _cell_length_c 26.9768(12) _cell_volume 2102.9(2) _diffrn_radiation_type Mo _diffrn_radiation_wavelength 0.71073 _exptl_absorpt_coefficient_mu 0.3417 _exptl_crystal_density_diffrn 1.48 _exptl_crystal_F_000 968 _cod_data_source_file mu0307.cif _cod_data_source_block mu0307b _cod_original_cell_volume 2102.9(7) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2101102 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x+1/2,y+1/2,-z+1/2 3 -x,-y,-z 4 x+1/2,-y+1/2,z+1/2 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv N(1) .2618(3) -.3237(2) .12510(10) .0310(8) N(3) .4972(3) -.2135(2) .11330(10) .0356(8) O(1) .6920(3) -.3545(2) .15330(10) .0480(8) O(2) .2471(3) -.1214(2) .08080(10) .0471(8) O(3) .1508(3) -.4150(2) .03110(10) .0454(8) O(4) -.0944(3) -.4735(4) .05770(10) .0723(12) C(2) .3254(4) -.2105(3) .10350(10) .0338(9) C(4) .5509(4) -.3286(3) .13930(10) .0340(10) C(5) .3946(4) -.4185(3) .14530(10) .0292(9) C(6) .0905(4) -.3620(3) .11450(10) .0369(11) C(7) .0523(4) -.4197(3) .06300(10) .0385(10) C(8) .6079(5) -.1196(3) .08940(10) .0419(12) C(11) .3799(4) -.4521(3) .19990(10) .0315(8) C(12) .2707(5) -.3833(3) .22810(10) .0416(12) C(13) .2618(5) -.4165(4) .27810(10) .0500(13) C(14) .3653(5) -.5146(4) .29970(10) .0524(14) C(15) .4756(5) -.5821(4) .27180(10) .0480(12) C(16) .4828(4) -.5522(3) .22220(10) .0387(11) C(21) .3992(4) -.5476(3) .11290(10) .0318(9) C(22) .4991(4) -.5546(3) .07300(10) .0407(11) C(23) .4908(5) -.6675(4) .04180(10) .0506(13) C(24) .3832(5) -.7736(4) .04940(10) .0521(13) C(25) .2848(5) -.7676(3) .08910(10) .0468(12) C(26) .2922(4) -.6560(3) .12040(10) .0385(10) C(31) .6768(4) -.0018(3) .12090(10) .0341(10) C(32) .6446(4) .0170(3) .17000(10) .0378(10) C(33) .7140(4) .1247(3) .19780(10) .0403(11) C(34) .8159(4) .2155(3) .17550(10) .0377(10) C(35) .8484(4) .2035(3) .12680(10) .0416(11) C(36) .7806(4) .0937(3) .09960(10) .0373(10) Cl(1) .91280(10) .34850(10) .21020(10) .0551(3) Cl(2) .82300(10) .07780(10) .03810(10) .0621(4) H(4) -.099(5) -.523(4) .0336(15) ? H(12) .204(5) -.308(4) .2169(15) ? H(13) .191(4) -.368(3) .2954(12) ? H(14) .369(5) -.533(4) .3301(14) ? H(15) .554(4) -.646(3) .2846(12) ? H(16) .562(5) -.598(3) .2028(12) ? H(22) .584(4) -.480(3) .0690(11) ? H(23) .558(5) -.670(4) .0174(14) ? H(24) .391(5) -.853(4) .0259(13) ? H(25) .211(5) -.841(4) .0942(13) ? H(26) .231(4) -.648(3) .1476(12) ? H(32) .571(5) -.047(3) .1840(12) ? H(33) .694(4) .134(3) .2321(12) ? H(35) .903(4) .263(3) .1111(12) ? H(601) .057(3) -.429(3) .1377(10) ? H(602) .018(4) -.285(3) .1174(11) ? H(801) .543(5) -.084(4) .0602(14) ? H(802) .704(5) -.173(4) .0765(14) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C(5) N(1) C(2) 112.1(4) C(6) N(1) C(5) 124.5(4) C(8) N(3) C(2) 122.4(5) N(3) C(2) N(1) 107.6(5) O(2) C(2) N(3) 125.7(5) C(5) C(4) N(3) 106.7(5) C(4) C(5) N(1) 100.2(4) C(11) C(5) C(4) 110.2(4) C(21) C(5) C(4) 110.3(4) C(7) C(6) N(1) 114.0(5) C(6) C(7) O(3) 122.7(5) C(31) C(8) N(3) 115.9(5) C(16) C(11) C(5) 118.9(5) C(13) C(12) C(11) 120.1(6) C(15) C(14) C(13) 119.9(6) C(15) C(16) C(11) 120.2(6) C(26) C(21) C(5) 119.8(5) C(23) C(22) C(21) 120.4(5) C(25) C(24) C(23) 119.3(6) C(25) C(26) C(21) 120.6(5) C(36) C(31) C(8) 118.5(5) C(33) C(32) C(31) 121.7(5) C(35) C(34) C(33) 122.1(5) Cl(1) C(34) C(35) 118.1(5) C(35) C(36) C(31) 121.1(5) Cl(2) C(36) C(35) 118.8(4) C(6) N(1) C(2) 120.6(5) C(4) N(3) C(2) 112.6(4) C(8) N(3) C(4) 123.8(5) O(2) C(2) N(1) 126.7(5) O(1) C(4) N(3) 126.0(5) C(5) C(4) O(1) 127.3(5) C(11) C(5) N(1) 112.6(4) C(21) C(5) N(1) 110.2(4) C(21) C(5) C(11) 112.6(4) O(4) C(7) O(3) 125.3(5) C(6) C(7) O(4) 112.0(5) C(12) C(11) C(5) 121.9(5) C(16) C(11) C(12) 119.2(5) C(14) C(13) C(12) 120.1(6) C(16) C(15) C(14) 120.5(6) C(22) C(21) C(5) 121.5(5) C(26) C(21) C(22) 118.5(5) C(24) C(23) C(22) 120.6(6) C(26) C(25) C(24) 120.7(6) C(32) C(31) C(8) 123.7(5) C(36) C(31) C(32) 117.8(5) C(34) C(33) C(32) 118.6(5) Cl(1) C(34) C(33) 119.8(5) C(36) C(35) C(34) 118.7(5) Cl(2) C(36) C(31) 120.1(4) H(4) O(4) C(7) 109.(4) H(601) C(6) C(7) 108.(2) H(602) C(6) C(7) 107.(3) H(801) C(8) N(3) 106.(3) H(802) C(8) N(3) 110.(3) H(802) C(8) H(801) 107.(4) H(12) C(12) C(13) 115.(4) H(13) C(13) C(14) 122.(3) H(14) C(14) C(15) 117.(4) H(15) C(15) C(16) 115.(3) H(16) C(16) C(15) 121.(3) H(22) C(22) C(23) 121.(3) H(23) C(23) C(24) 121.(4) H(24) C(24) C(25) 126.(3) H(25) C(25) C(26) 121.(3) H(26) C(26) C(25) 124.(3) H(32) C(32) C(33) 121.(3) H(33) C(33) C(34) 121.(3) H(35) C(35) C(36) 117.(3) H(601) C(6) N(1) 111.(3) H(602) C(6) N(1) 111.(3) H(602) C(6) H(601) 106.(4) H(801) C(8) C(31) 110.(3) H(802) C(8) C(31) 109.(3) H(12) C(12) C(11) 125.(4) H(13) C(13) C(12) 117.(3) H(14) C(14) C(13) 123.(4) H(15) C(15) C(14) 124.(3) H(16) C(16) C(11) 119.(3) H(22) C(22) C(21) 119.(3) H(23) C(23) C(22) 118.(4) H(24) C(24) C(23) 114.(3) H(25) C(25) C(24) 119.(3) H(26) C(26) C(21) 115.(3) H(32) C(32) C(31) 117.(3) H(33) C(33) C(32) 120.(3) H(35) C(35) C(34) 124.(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C(2) N(1) 1.362(6) C(6) N(1) 1.435(7) C(4) N(3) 1.373(6) C(4) O(1) 1.196(6) C(7) O(3) 1.213(6) C(5) C(4) 1.549(8) C(21) C(5) 1.533(7) C(31) C(8) 1.507(8) C(16) C(11) 1.384(7) C(14) C(13) 1.367(9) C(16) C(15) 1.376(8) C(26) C(21) 1.385(7) C(24) C(23) 1.372(9) C(26) C(25) 1.374(7) C(36) C(31) 1.401(7) C(34) C(33) 1.374(8) Cl(1) C(34) 1.745(6) Cl(2) C(36) 1.725(6) C(5) N(1) 1.483(6) C(2) N(3) 1.387(7) C(8) N(3) 1.458(6) C(2) O(2) 1.210(6) C(7) O(4) 1.288(7) C(11) C(5) 1.522(7) C(7) C(6) 1.508(8) C(12) C(11) 1.378(7) C(13) C(12) 1.392(8) C(15) C(14) 1.371(9) C(22) C(21) 1.392(7) C(23) C(22) 1.381(8) C(25) C(24) 1.378(8) C(32) C(31) 1.380(7) C(33) C(32) 1.382(7) C(35) C(34) 1.363(8) C(36) C(35) 1.384(7) H(4) O(4) 0.81(6) H(602) C(6) 0.96(5) H(802) C(8) 1.01(6) H(13) C(13) 0.90(5) H(15) C(15) 0.93(5) H(22) C(22) 1.01(5) H(24) C(24) 1.00(5) H(26) C(26) 0.92(5) H(33) C(33) 0.95(5) H(601) C(6) 0.96(4) H(801) C(8) 0.98(5) H(12) C(12) 0.95(6) H(14) C(14) 0.84(6) H(16) C(16) 0.96(5) H(23) C(23) 0.88(6) H(25) C(25) 0.95(6) H(32) C(32) 0.96(5) H(35) C(35) 0.86(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 101681445