#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/32/2003294.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_2003294 loop_ _publ_author_name 'Dupont, L.' 'Pirotte, B.' 'Masereel, B.' 'Delarge, J.' 'Geczy, J.' _publ_contact_author ; Dr L. Dupont Unit\'e de Cristallographie Institut de Physique B5 Universit\'e de Liege au Sart Tilman B-4000 Liege Belgium ; _publ_section_title ; Nimesulide ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 507 _journal_page_last 509 _journal_paper_doi 10.1107/S0108270194010334 _journal_volume 51 _journal_year 1995 _chemical_compound_source 'Therabel Research, Bruxelles' _chemical_formula_analytical 'C13 H12 N2 O5 S' _chemical_formula_sum 'C13 H12 N2 O5 S' _chemical_formula_weight 308.31 _chemical_name_common Nimesulide _chemical_name_systematic ; 4-nitro-2-phenoxymethanesulfonanilide ; _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 SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 92.368(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 33.657(3) _cell_length_b 5.1305(3) _cell_length_c 16.0816(10) _cell_measurement_reflns_used 36 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 32.35 _cell_measurement_theta_min 28.31 _cell_volume 2774.6(3) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1988a)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1988b)' _computing_molecular_graphics 'PLUTO (Motherwell & Clegg, 1976)' _computing_publication_material SHELXL-93 _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Stoe-Siemens AED 4-circle diffractometer' _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 1999 _diffrn_reflns_theta_max 57.52 _diffrn_reflns_theta_min 2.63 _diffrn_standards_decay_% 3.0 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 2.310 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6396 _exptl_absorpt_correction_type semi-empiric _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.476 _exptl_crystal_description prism _exptl_crystal_F_000 1280 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.221 _refine_diff_density_min -0.211 _refine_ls_extinction_coef 0.0016(2) _refine_ls_extinction_method 'F~c~^*^ = kF~c~[1 + 0.001(F~c~)^2^\l^3^/sin(2\q)' _refine_ls_goodness_of_fit_all 1.088 _refine_ls_goodness_of_fit_obs 1.248 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 1908 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.189 _refine_ls_restrained_S_obs 1.248 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_obs 0.0401 _refine_ls_shift/esd_max 0.008 _refine_ls_shift/esd_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ;calc w = 1/[\s^2^(F~o~^2^) + (0.0776P)^2^ + 0.0512P] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1325 _refine_ls_wR_factor_obs 0.1146 _reflns_number_observed 1355 _reflns_number_total 1910 _reflns_observed_criterion >2sigma(I) _cod_data_source_file pa1137.cif _cod_data_source_block sm0150 _cod_original_cell_volume 2774.5(3) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2003294 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 C1 0.069(2) 0.002(2) -0.001(2) 0.059(2) 0.001(2) 0.057(2) C2 0.0465(15) 0.0025(14) 0.0049(12) 0.049(2) -0.0016(14) 0.044(2) C3 0.059(2) 0.010(2) 0.0118(14) 0.064(2) -0.002(2) 0.047(2) C4 0.061(2) 0.001(2) 0.0105(13) 0.074(2) 0.004(2) 0.040(2) C5 0.054(2) -0.006(2) -0.0008(13) 0.060(2) 0.007(2) 0.042(2) C6 0.051(2) 0.006(2) 0.0049(14) 0.065(2) 0.007(2) 0.057(2) C7 0.051(2) 0.004(2) 0.0105(13) 0.068(2) 0.005(2) 0.041(2) C8 0.054(2) 0.016(2) 0.0198(15) 0.070(2) 0.012(2) 0.052(2) C9 0.075(2) 0.012(2) -0.002(2) 0.078(2) -0.015(2) 0.060(2) C10 0.055(2) 0.009(2) 0.000(2) 0.093(3) -0.001(2) 0.082(2) C11 0.068(2) 0.017(2) 0.027(2) 0.075(3) 0.007(2) 0.085(2) C12 0.081(3) 0.002(2) 0.017(2) 0.074(3) -0.021(2) 0.086(3) C13 0.058(2) -0.008(2) 0.009(2) 0.077(2) -0.003(2) 0.072(2) N1 0.0538(14) 0.0120(13) 0.0133(11) 0.064(2) 0.0088(13) 0.0481(14) N2 0.060(2) -0.006(2) -0.0037(13) 0.079(2) 0.017(2) 0.053(2) O1 0.0736(14) 0.0121(11) 0.0166(11) 0.0514(13) -0.0078(11) 0.0620(13) O2 0.0809(14) 0.0150(12) 0.0189(11) 0.072(2) 0.0250(12) 0.0550(13) O3 0.101(2) -0.001(2) 0.0157(13) 0.101(2) 0.0238(14) 0.0549(14) O4 0.075(2) 0.024(2) 0.0057(15) 0.134(3) 0.059(2) 0.102(2) O5 0.0745(14) 0.0422(15) 0.0244(11) 0.111(2) 0.0238(14) 0.0546(13) S1 0.0578(5) 0.0094(4) 0.0102(3) 0.0480(5) 0.0052(4) 0.0483(5) loop_ _atom_site_label _atom_site_occupancy _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_refinement_flags _atom_site_type_symbol C1 1 0.48964(10) 0.6862(7) 0.1404(2) 0.0619(9) Uani d . C H1A 1 0.4786(3) 0.8099(18) 0.1779(9) 0.074(6) Uiso calc R H H1B 1 0.4935(4) 0.7685(23) 0.0878(3) 0.074(6) Uiso calc R H H1C 1 0.5147(2) 0.6246(8) 0.1633(11) 0.074(6) Uiso calc R H C2 1 0.40549(8) 0.7137(6) 0.0321(2) 0.0464(7) Uani d . C C3 1 0.42703(9) 0.7117(6) -0.0388(2) 0.0563(8) Uani d . C H3 1 0.44798(9) 0.5950(6) -0.0433(2) 0.088(4) Uiso calc R H C4 1 0.41775(9) 0.8823(7) -0.1037(2) 0.0582(8) Uani d . C H4 1 0.43224(9) 0.8813(7) -0.1517(2) 0.088(4) Uiso calc R H C5 1 0.38691(9) 1.0515(6) -0.0955(2) 0.0519(8) Uani d . C C6 1 0.36387(9) 1.0571(7) -0.0264(2) 0.0576(8) Uani d . C H6 1 0.34273(9) 1.1728(7) -0.0228(2) 0.088(4) Uiso calc R H C7 1 0.37342(8) 0.8849(6) 0.0370(2) 0.0531(8) Uani d . C C8 1 0.32013(9) 1.0199(7) 0.1220(2) 0.0580(9) Uani d . C C9 1 0.28473(11) 0.9546(8) 0.0824(2) 0.0711(10) Uani d . C H9 1 0.28325(11) 0.8162(8) 0.0450(2) 0.088(4) Uiso calc R H C10 1 0.25139(10) 1.0975(8) 0.0990(2) 0.0769(11) Uani d . C H10 1 0.22710(10) 1.0566(8) 0.0725(2) 0.088(4) Uiso calc R H C11 1 0.25387(11) 1.2985(8) 0.1542(2) 0.0752(10) Uani d . C H11 1 0.23135(11) 1.3956(8) 0.1650(2) 0.088(4) Uiso calc R H C12 1 0.28944(12) 1.3575(8) 0.1935(2) 0.0802(11) Uani d . C H12 1 0.29090(12) 1.4949(8) 0.2312(2) 0.088(4) Uiso calc R H C13 1 0.32284(10) 1.2184(7) 0.1784(2) 0.0686(10) Uani d . C H13 1 0.34694(10) 1.2578(7) 0.2058(2) 0.088(4) Uiso calc R H N1 1 0.41351(7) 0.5527(5) 0.10176(14) 0.0549(7) Uani d . N H1 1 0.4000 0.5946 0.1519 0.088(4) Uiso d . H N2 1 0.37749(9) 1.2385(6) -0.1622(2) 0.0642(7) Uani d . N O1 1 0.46955(6) 0.2742(4) 0.05712(13) 0.0620(6) Uani d . O O2 1 0.45181(7) 0.2970(5) 0.20453(13) 0.0689(7) Uani d . O O3 1 0.40020(8) 1.2561(6) -0.21917(14) 0.0851(8) Uani d . O O4 1 0.34810(8) 1.3751(7) -0.1574(2) 0.1036(11) Uani d . O O5 1 0.35423(7) 0.8698(5) 0.11083(13) 0.0793(8) Uani d . O S1 1 0.45701(2) 0.42371(14) 0.12648(4) 0.0511(3) Uani d . S loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0181 0.009 H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0311 0.018 O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0492 0.032 S S 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.3331 0.556 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 S1 C1 H1A 109.47(11) ? S1 C1 H1B 109.47(10) ? H1A C1 H1B 109.5 ? S1 C1 H1C 109.47(11) ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? C3 C2 C7 119.1(3) yes C3 C2 N1 124.3(3) yes C7 C2 N1 116.6(2) yes C2 C3 C4 120.6(3) yes C2 C3 H3 119.7(2) ? C4 C3 H3 119.7(2) ? C5 C4 C3 118.6(3) yes C5 C4 H4 120.7(2) ? C3 C4 H4 120.7(2) ? C4 C5 C6 123.1(3) yes C4 C5 N2 119.3(3) yes C6 C5 N2 117.6(3) yes C7 C6 C5 117.4(3) yes C7 C6 H6 121.3(2) ? C5 C6 H6 121.3(2) ? C6 C7 O5 124.8(3) yes C6 C7 C2 121.3(3) yes O5 C7 C2 113.8(3) yes C13 C8 C9 121.6(3) yes C13 C8 O5 117.6(3) yes C9 C8 O5 120.5(3) yes C8 C9 C10 118.7(3) yes C8 C9 H9 120.6(2) ? C10 C9 H9 120.6(2) ? C11 C10 C9 120.1(3) yes C11 C10 H10 119.9(2) ? C9 C10 H10 119.9(2) ? C10 C11 C12 120.0(3) yes C10 C11 H11 120.0(2) ? C12 C11 H11 120.0(2) ? C13 C12 C11 121.1(4) yes C13 C12 H12 119.5(2) ? C11 C12 H12 119.5(2) ? C12 C13 C8 118.5(3) yes C12 C13 H13 120.8(2) ? C8 C13 H13 120.8(2) ? C2 N1 S1 124.7(2) yes C2 N1 H1 116.9(2) ? S1 N1 H1 109.5(2) ? O4 N2 O3 122.7(3) yes O4 N2 C5 118.9(3) yes O3 N2 C5 118.4(3) yes C7 O5 C8 119.7(2) yes O2 S1 O1 119.40(14) yes O2 S1 N1 104.82(12) yes O1 S1 N1 108.43(13) yes O2 S1 C1 109.7(2) yes O1 S1 C1 108.01(14) yes N1 S1 C1 105.7(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 S1 1.747(3) yes C1 H1A 0.96 ? C1 H1B 0.96 ? C1 H1C 0.96 ? C2 C3 1.377(4) yes C2 C7 1.396(4) yes C2 N1 1.409(4) yes C3 C4 1.387(4) yes C3 H3 0.93 ? C4 C5 1.364(4) yes C4 H4 0.93 ? C5 C6 1.382(4) yes C5 N2 1.464(4) yes C6 C7 1.377(4) yes C6 H6 0.93 ? C7 O5 1.377(3) yes C8 C13 1.364(5) yes C8 C9 1.369(5) yes C8 O5 1.400(4) yes C9 C10 1.376(5) yes C9 H9 0.93 ? C10 C11 1.360(5) yes C10 H10 0.93 ? C11 C12 1.364(5) yes C11 H11 0.93 ? C12 C13 1.362(5) yes C12 H12 0.93 ? C13 H13 0.93 ? N1 S1 1.640(2) yes N1 H1 0.966(2) ? N2 O4 1.217(4) yes N2 O3 1.221(3) yes O1 S1 1.431(2) yes O2 S1 1.431(2) yes 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 C7 C2 C3 C4 1.8(5) ? N1 C2 C3 C4 -178.2(3) ? C2 C3 C4 C5 0.0(5) ? C3 C4 C5 C6 -1.5(5) ? C3 C4 C5 N2 178.1(3) ? C4 C5 C6 C7 1.0(5) ? N2 C5 C6 C7 -178.5(3) ? C5 C6 C7 O5 178.2(3) ? C5 C6 C7 C2 0.9(5) ? C3 C2 C7 C6 -2.3(5) ? N1 C2 C7 C6 177.7(3) ? C3 C2 C7 O5 -179.8(3) ? N1 C2 C7 O5 0.1(4) ? C13 C8 C9 C10 1.4(5) ? O5 C8 C9 C10 176.0(3) ? C8 C9 C10 C11 -0.4(6) ? C9 C10 C11 C12 -0.4(6) ? C10 C11 C12 C13 0.1(6) ? C11 C12 C13 C8 0.9(6) ? C9 C8 C13 C12 -1.7(5) ? O5 C8 C13 C12 -176.4(3) ? C3 C2 N1 S1 24.4(4) ? C7 C2 N1 S1 -155.6(2) yes C4 C5 N2 O4 174.4(3) ? C6 C5 N2 O4 -6.0(4) yes C4 C5 N2 O3 -7.7(5) ? C6 C5 N2 O3 171.9(3) yes C6 C7 O5 C8 6.2(5) yes C2 C7 O5 C8 -176.3(3) ? C13 C8 O5 C7 -111.4(4) yes C9 C8 O5 C7 73.8(4) ? C2 N1 S1 O2 175.1(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4339