#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/40/2004093.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_2004093 loop_ _publ_author_name 'Bolger, J.' 'Gourdon, A.' _publ_section_title ; 1-Amino-2-nitro-4,5-bis(p-toluenesulfonamido)benzene ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2395 _journal_page_last 2397 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C20 H20 N4 O6 S2' _chemical_formula_sum 'C20 H20 N4 O6 S2' _chemical_formula_weight 476.522 _chemical_melting_point 438.15 _chemical_name_systematic ; 1-Amino-2-nitro-4,5-bis(p-toluenesulfonamido)-benzene ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 69.69(5) _cell_angle_beta 80.57(6) _cell_angle_gamma 86.87(5) _cell_formula_units_Z 2 _cell_length_a 7.6430(10) _cell_length_b 11.578(2) _cell_length_c 13.117(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 297 _cell_measurement_theta_max 16 _cell_measurement_theta_min 13 _cell_volume 1073.9(5) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CRYSTALS RC85 (Watkin, Carruthers & Betteridge, 1985)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material CRYSTALS _computing_structure_refinement CRYSTALS _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 297 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source xray_tube _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.010 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3962 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 2 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.2807 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.474 _exptl_crystal_description prism _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _refine_diff_density_max .29 _refine_diff_density_min -.26 _refine_ls_extinction_coef 75(7) _refine_ls_extinction_method 'Zachariansen Gaussian coefficient = 75(7)' _refine_ls_goodness_of_fit_obs 2.13 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 350 _refine_ls_number_reflns 2994 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs .034 _refine_ls_shift/esd_max .001 _refine_ls_shift/esd_mean .0015 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme unit _refine_ls_wR_factor_obs .034 _reflns_number_observed 2994 _reflns_number_total 3762 _reflns_observed_criterion >3sigma(I) _[local]_cod_data_source_file bk1112.cif _[local]_cod_data_source_block Aminobenz _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '165_C' was changed to '438.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1074.0(10) _cod_database_code 2004093 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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_thermal_displace_type _atom_site_type_symbol C(1) .3099(3) .2478(2) .2889(2) .0315 Uij C C(2) .4883(3) .2869(2) .2747(2) .0299 Uij C C(3) .5781(4) .2485(2) .3627(2) .0368 Uij C C(4) .4983(4) .1729(2) .4657(2) .0411 Uij C C(5) .3198(4) .1365(3) .4833(2) .0428 Uij C C(6) .2301(4) .1769(3) .3917(2) .0409 Uij C N(7) .6057(4) .1333(2) .5524(2) .0563 Uij N O(71) .7660(4) .1553(3) .5291(2) .0713 Uij O O(72) .5338(4) .0765(3) .6468(2) .0765 Uij O N(8) .2306(5) .0668(3) .5809(2) .0620 Uij N N(10) .2227(3) .2882(2) .1966(2) .0345 Uij N S(1) .05747(8) .22257(6) .17130(6) .0346 Uij S O(11) -.0271(2) .3191(2) .0942(2) .0434 Uij O O(12) -.0440(2) .1546(2) .2746(2) .0477 Uij O C(11) .1460(3) .1182(2) .1071(2) .0338 Uij C C(12) .1639(4) .1512(3) -.0053(3) .0457 Uij C C(13) .2307(4) .0672(3) -.0549(3) .0521 Uij C C(14) .2794(4) -.0494(3) .0057(3) .0450 Uij C C(15) .2605(4) -.0799(3) .1181(3) .0547 Uij C C(16) .1949(4) .0016(3) .1696(3) .0509 Uij C C(17) .3501(5) -0.1394(4) -.0489(4) .0642 Uij C N(20) .5704(3) .3649(2) .1691(2) .0306 Uij N S(2) .56435(8) .51396(6) .14181(6) .0350 Uij S O(21) .6551(3) .5658(2) .0322(2) .0468 Uij O O(22) .3840(2) .5447(2) .1701(2) .0504 Uij O C(21) .6893(3) .5487(2) .2288(2) .0358 Uij C C(22) .8728(4) .5439(3) .2064(2) .0418 Uij C C(23) .9711(4) .5774(3) .2706(3) .0511 Uij C C(24) .8935(5) .6154(3) .3552(3) .0571 Uij C C(25) .7108(5) .6163(4) .3779(3) .0661 Uij C C(26) .6081(4) .5835(3) .3145(3) .0567 Uij C C(27) 1.0065(8) .6575(5) .4197(5) .0819 Uij C H(3) .697(4) .275(3) .352(3) .0700 Uiso H H(6) .116(4) .156(3) .402(3) .0700 Uiso H H(10) .276(4) .338(3) .136(3) .0700 Uiso H H(12) .129(4) .227(3) -.042(3) .0700 Uiso H H(13) .237(4) .088(3) -0.128(3) .0700 Uiso H H(15) .290(4) -0.158(3) .158(3) .0700 Uiso H H(16) .179(4) -.017(3) .246(3) .0700 Uiso H H(20) .660(4) .342(3) .142(3) .0700 Uiso H H(22) .926(4) .520(3) .148(3) .0700 Uiso H H(23) 1.084(5) .575(3) .258(3) .0700 Uiso H H(25) .652(4) .645(3) .433(3) .0700 Uiso H H(26) .486(5) .588(3) .325(3) .0700 Uiso H H(81) .129(5) .044(3) .580(3) .0700 Uiso H H(82) .282(5) .045(3) .635(3) .0700 Uiso H H(171) .282(5) -0.210(3) -.023(3) .0700 Uiso H H(172) .447(5) -0.167(3) -.033(3) .0700 Uiso H H(173) .330(5) -0.117(3) -0.118(3) .0700 Uiso H H(271) 1.100(5) .607(3) .434(3) .0700 Uiso H H(272) .942(5) .644(3) .495(3) .0700 Uiso H H(273) 1.010(5) .744(3) .392(3) .0700 Uiso H 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 C(1) 0.0330(10) 0.0310(10) 0.0330(10) -0.0130(10) 0.0010(10) -0.0050(10) C C(2) 0.0310(10) 0.0280(10) 0.0300(10) -0.0100(10) 0.0000(10) -0.0040(10) C C(3) 0.0400(10) 0.0360(10) 0.0350(10) -0.0130(10) -0.0060(10) -0.0020(10) C C(4) 0.060(2) 0.0380(10) 0.0310(10) -0.0090(10) -0.0100(10) -0.0020(10) C C(5) 0.067(2) 0.037(2) 0.0310(10) -0.0090(10) 0.0040(10) -0.0140(10) C C(6) 0.043(2) 0.048(2) 0.038(2) -0.0160(10) 0.0080(10) -0.0170(10) C N(7) 0.092(2) 0.051(2) 0.041(2) -0.0080(10) -0.025(2) -0.003(2) N O(71) 0.088(2) 0.092(2) 0.063(2) -0.0070(10) -0.0410(10) -0.021(2) O O(72) 0.121(2) 0.103(2) 0.0350(10) 0.0030(10) -0.0210(10) -0.002(2) O N(8) 0.095(3) 0.072(2) 0.036(2) -0.0050(10) 0.007(2) -0.034(2) N N(10) 0.0300(10) 0.0420(10) 0.0370(10) -0.0100(10) -0.0017(9) -0.0138(9) N S(1) 0.0224(3) 0.0408(4) 0.0503(4) -0.0188(3) -0.0011(3) -0.0066(3) S O(11) 0.0300(10) 0.0450(10) 0.0720(10) -0.0240(10) -0.0162(9) 0.0057(8) O O(12) 0.0350(10) 0.0650(10) 0.0600(10) -0.0230(10) 0.0108(9) -0.0220(10) O C(11) 0.0250(10) 0.0350(10) 0.050(2) -0.0150(10) -0.0080(10) -0.0050(10) C C(12) 0.046(2) 0.038(2) 0.053(2) -0.0130(10) -0.0100(10) 0.0000(10) C C(13) 0.051(2) 0.058(2) 0.055(2) -0.027(2) -0.008(2) -0.0020(10) C C(14) 0.0320(10) 0.050(2) 0.082(2) -0.036(2) -0.0140(10) 0.0000(10) C C(15) 0.056(2) 0.041(2) 0.080(3) -0.019(2) -0.022(2) 0.0120(10) C C(16) 0.052(2) 0.048(2) 0.053(2) -0.014(2) -0.016(2) 0.0040(10) C C(17) 0.049(2) 0.076(3) 0.125(4) -0.067(3) -0.023(2) 0.008(2) C N(20) 0.0260(10) 0.0360(10) 0.0300(10) -0.0097(9) -0.0002(8) -0.0053(9) N S(2) 0.0296(3) 0.0342(3) 0.0420(4) -0.0037(3) -0.0101(3) -0.0058(3) S O(21) 0.0560(10) 0.0580(10) 0.0380(10) 0.0054(9) -0.0148(9) -0.0240(10) O O(22) 0.0310(10) 0.0480(10) 0.089(2) -0.0200(10) -0.0160(10) 0.0057(9) O C(21) 0.0360(10) 0.0300(10) 0.042(2) -0.0100(10) -0.0080(10) -0.0040(10) C C(22) 0.0350(10) 0.045(2) 0.048(2) -0.0180(10) -0.0070(10) -0.0010(10) C C(23) 0.041(2) 0.058(2) 0.072(2) -0.027(2) -0.021(2) -0.0010(10) C C(24) 0.070(2) 0.054(2) 0.069(2) -0.030(2) -0.027(2) 0.000(2) C C(25) 0.077(3) 0.087(3) 0.073(3) -0.056(2) -0.009(2) 0.007(2) C C(26) 0.044(2) 0.071(2) 0.069(2) -0.037(2) -0.002(2) 0.002(2) C C(27) 0.120(4) 0.087(3) 0.115(4) -0.062(3) -0.062(3) 0.012(3) C loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 International_Tables_Vol_IV_Table_2.3.1 H .0 .0 International_Tables_Vol_IV_Table_2.3.1 O .008 .006 International_Tables_Vol_IV_Table_2.3.1 N .004 .003 International_Tables_Vol_IV_Table_2.3.1 S .132 .159 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -2 -7 19 -2 8 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 C(6) C(1) C(2) 119.0(2) yes N(10) C(1) C(2) 117.6(2) yes N(10) C(1) C(6) 123.4(2) yes C(3) C(2) C(1) 119.3(2) yes N(20) C(2) C(1) 119.5(2) yes N(20) C(2) C(3) 121.2(2) yes C(4) C(3) C(2) 121.3(3) yes H(3) C(3) C(2) 118.(2) ? H(3) C(3) C(4) 120.(2) ? C(5) C(4) C(3) 120.8(2) yes N(7) C(4) C(3) 117.3(3) yes N(7) C(4) C(5) 121.9(3) yes C(6) C(5) C(4) 116.9(2) yes N(8) C(5) C(4) 124.7(3) yes N(8) C(5) C(6) 118.4(3) yes C(5) C(6) C(1) 122.7(3) yes H(6) C(6) C(1) 119.(2) ? H(6) C(6) C(5) 118.(2) ? O(71) N(7) C(4) 118.9(3) yes O(72) N(7) C(4) 118.6(3) yes O(72) N(7) O(71) 122.5(3) yes H(81) N(8) C(5) 116.(3) ? H(82) N(8) C(5) 119.(3) ? H(82) N(8) H(81) 125.(4) ? S(1) N(10) C(1) 128.6(2) ? H(10) N(10) C(1) 119.(2) ? H(10) N(10) S(1) 109.(2) ? O(11) S(1) N(10) 105.70(10) yes O(12) S(1) N(10) 107.60(10) yes O(12) S(1) O(11) 118.80(10) ? C(11) S(1) N(10) 108.20(10) ? C(11) S(1) O(11) 108.10(10) ? C(11) S(1) O(12) 108.10(10) ? C(12) C(11) S(1) 120.0(2) ? C(16) C(11) S(1) 119.9(2) ? C(16) C(11) C(12) 120.0(3) ? C(13) C(12) C(11) 119.5(3) ? H(12) C(12) C(11) 117.(2) ? H(12) C(12) C(13) 124.(2) ? C(14) C(13) C(12) 121.5(3) ? H(13) C(13) C(12) 119.(2) ? H(13) C(13) C(14) 119.(2) ? C(15) C(14) C(13) 117.7(3) ? C(17) C(14) C(13) 120.9(4) ? C(17) C(14) C(15) 121.4(3) ? C(16) C(15) C(14) 122.1(3) ? H(15) C(15) C(14) 117.(2) ? H(15) C(15) C(16) 121.(2) ? C(15) C(16) C(11) 119.2(3) ? H(16) C(16) C(11) 117.(2) ? H(16) C(16) C(15) 124.(2) ? H(171) C(17) C(14) 111.(2) ? H(172) C(17) C(14) 113.(3) ? H(172) C(17) H(171) 101.(3) ? H(173) C(17) C(14) 113.(2) ? H(173) C(17) H(171) 96.(3) ? H(173) C(17) H(172) 120.(4) ? S(2) N(20) C(2) 118.5(2) ? H(20) N(20) C(2) 118.(3) ? H(20) N(20) S(2) 113.(3) ? O(21) S(2) N(20) 105.30(10) yes O(22) S(2) N(20) 106.70(10) yes O(22) S(2) O(21) 120.90(10) yes C(21) S(2) N(20) 108.20(10) ? C(21) S(2) O(21) 107.40(10) ? C(21) S(2) O(22) 107.80(10) ? C(22) C(21) S(2) 118.5(2) ? C(26) C(21) S(2) 120.9(2) ? C(26) C(21) C(22) 120.6(3) ? C(23) C(22) C(21) 118.6(3) ? H(22) C(22) C(21) 120.(2) ? H(22) C(22) C(23) 122.(2) ? C(24) C(23) C(22) 122.0(3) ? H(23) C(23) C(22) 120.(2) ? H(23) C(23) C(24) 118.(2) ? C(25) C(24) C(23) 118.3(3) ? C(27) C(24) C(23) 120.2(4) ? C(27) C(24) C(25) 121.4(4) ? C(26) C(25) C(24) 121.0(3) ? H(25) C(25) C(24) 121.(2) ? H(25) C(25) C(26) 118.(2) ? C(25) C(26) C(21) 119.4(3) ? H(26) C(26) C(21) 118.(2) ? H(26) C(26) C(25) 123.(2) ? H(271) C(27) C(24) 110.(2) ? H(272) C(27) C(24) 110.(2) ? H(272) C(27) H(271) 102.(3) ? H(273) C(27) C(24) 108.(2) ? H(273) C(27) H(271) 127.(3) ? H(273) C(27) H(272) 99.(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C(1) C(2) 1.422(3) yes C(1) C(6) 1.371(4) yes C(1) N(10) 1.401(3) yes C(2) C(3) 1.368(3) yes C(2) N(20) 1.427(3) yes C(3) C(4) 1.389(4) yes C(3) H(3) 0.95(3) ? C(4) C(5) 1.408(4) yes C(4) N(7) 1.443(4) yes C(5) C(6) 1.407(4) yes C(5) N(8) 1.346(4) yes C(6) H(6) 0.90(3) ? N(7) O(71) 1.231(4) yes N(7) O(72) 1.232(3) yes N(8) H(81) 0.84(3) ? N(8) H(82) 0.83(3) ? N(10) S(1) 1.643(2) yes N(10) H(10) 0.85(3) ? S(1) O(11) 1.429(2) yes S(1) O(12) 1.428(2) yes S(1) C(11) 1.749(3) ? C(11) C(12) 1.374(4) ? C(11) C(16) 1.382(4) ? C(12) C(13) 1.380(4) ? C(12) H(12) 0.89(3) ? C(13) C(14) 1.375(4) ? C(13) H(13) 0.90(3) ? C(14) C(15) 1.376(5) ? C(14) C(17) 1.490(5) ? C(15) C(16) 1.371(4) ? C(15) H(15) 0.91(3) ? C(16) H(16) 0.93(3) ? C(17) H(171) 0.92(3) ? C(17) H(172) 0.82(3) ? C(17) H(173) 0.89(3) ? N(20) S(2) 1.636(2) ? N(20) H(20) 0.80(3) ? S(2) O(21) 1.424(2) yes S(2) O(22) 1.426(2) yes S(2) C(21) 1.759(3) ? C(21) C(22) 1.387(4) ? C(21) C(26) 1.369(4) ? C(22) C(23) 1.376(4) ? C(22) H(22) 0.93(3) ? C(23) C(24) 1.368(5) ? C(23) H(23) 0.85(3) ? C(24) C(25) 1.380(5) ? C(24) C(27) 1.507(5) ? C(25) C(26) 1.384(5) ? C(25) H(25) 0.93(3) ? C(26) H(26) 0.92(3) ? C(27) H(271) 0.90(3) ? C(27) H(272) 0.99(3) ? C(27) H(273) 0.94(3) ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 O(72) H(82) 2.02(4) . O(72) N(8) 2.623(5) . N(10) O(21) 2.911(3) 2_665 H(10) O(21) 2.09(3) 2_665 N(20) O(11) 3.148(3) 1_655 H(20) O(11) 2.39(4) 1_655 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 C(11) S(1) N(10) C(1) -87.3(3) S(1) N(10) C(1) C(2) 153.9(2) C(2) N(20) S(2) C(21) 65.6(2) N(20) S(2) C(21) C(22) 74.4(3) _journal_paper_doi 10.1107/S0108270195006950