#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/29/2222994.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_2222994 loop_ _publ_author_name 'Gowda, B. Thimme' 'Foro, Sabine' 'Shakuntala, K.' 'Fuess, Hartmut' _publ_section_title ; 2-Chlorobenzenesulfonamide ; _journal_coeditor_code BT5028 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2144 _journal_volume 65 _journal_year 2009 _chemical_formula_iupac 'C6 H6 Cl N O2 S' _chemical_formula_moiety 'C6 H6 Cl N O2 S' _chemical_formula_sum 'C6 H6 Cl N O2 S' _chemical_formula_weight 191.63 _chemical_name_systematic ; 2-Chlorobenzenesulfonamide ; _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.510(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.9550(10) _cell_length_b 14.848(3) _cell_length_c 7.7510(10) _cell_measurement_reflns_used 1188 _cell_measurement_temperature 299(2) _cell_measurement_theta_max 27.79 _cell_measurement_theta_min 2.63 _cell_volume 800.2(2) _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2009) ; _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2009) ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2009) ; _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 299(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector ; _diffrn_measurement_method ; Rotation method data acquisition using omega and phi scans. ; _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0081 _diffrn_reflns_av_sigmaI/netI 0.0109 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 1598 _diffrn_reflns_theta_full 26.35 _diffrn_reflns_theta_max 26.35 _diffrn_reflns_theta_min 2.74 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.684 _exptl_absorpt_correction_T_max 0.8423 _exptl_absorpt_correction_T_min 0.7350 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.141 _refine_diff_density_min -0.209 _refine_ls_abs_structure_details 'Flack (1983), 215 Friedel pairs' _refine_ls_abs_structure_Flack 0.04(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 106 _refine_ls_number_reflns 1031 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0224 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.004 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.2306P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.0599 _reflns_number_gt 1004 _reflns_number_total 1031 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt5028.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C c' _cod_database_code 2222994 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' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl1 0.56409(10) 0.10747(7) 0.84733(11) 0.0700(3) Uani d . 1 . . S S1 0.18379(8) 0.20974(3) 0.98884(8) 0.03276(14) Uani d . 1 . . O O1 -0.0067(3) 0.22742(12) 1.0448(3) 0.0486(5) Uani d . 1 . . O O2 0.3434(3) 0.23916(13) 1.0939(2) 0.0535(5) Uani d . 1 . . N N1 0.2010(4) 0.25747(15) 0.8048(3) 0.0396(5) Uani d D 1 . . H H11 0.309(3) 0.251(2) 0.755(4) 0.048 Uiso d D 1 . . H H12 0.105(4) 0.249(2) 0.740(3) 0.048 Uiso d D 1 . . C C1 0.1995(4) 0.09052(15) 0.9649(3) 0.0335(5) Uani d . 1 . . C C2 0.3626(4) 0.04740(18) 0.9082(4) 0.0443(6) Uani d . 1 . . C C3 0.3663(6) -0.0459(2) 0.8966(4) 0.0588(8) Uani d . 1 . . H H3 0.4755 -0.0751 0.8582 0.071 Uiso calc R 1 . . C C4 0.2078(7) -0.0951(2) 0.9421(4) 0.0674(10) Uani d . 1 . . H H4 0.2106 -0.1576 0.9341 0.081 Uiso calc R 1 . . C C5 0.0464(6) -0.05329(19) 0.9990(4) 0.0590(8) Uani d . 1 . . H H5 -0.0600 -0.0872 1.0292 0.071 Uiso calc R 1 . . C C6 0.0415(4) 0.04025(18) 1.0117(4) 0.0432(6) Uani d . 1 . . H H6 -0.0677 0.0689 1.0515 0.052 Uiso calc R 1 . . 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 0.0380(4) 0.0856(6) 0.0871(6) 0.0153(4) 0.0158(4) 0.0148(5) S1 0.0338(3) 0.0335(2) 0.0310(2) -0.0015(3) 0.00213(18) -0.0023(2) O1 0.0468(11) 0.0480(9) 0.0520(11) 0.0068(9) 0.0205(9) -0.0043(9) O2 0.0590(14) 0.0501(11) 0.0506(11) -0.0152(10) -0.0172(10) -0.0031(9) N1 0.0364(11) 0.0449(11) 0.0375(11) 0.0035(10) 0.0025(8) 0.0055(9) C1 0.0381(12) 0.0343(10) 0.0280(11) 0.0023(11) -0.0025(9) 0.0013(8) C2 0.0478(16) 0.0476(13) 0.0374(13) 0.0118(13) -0.0008(12) 0.0047(11) C3 0.078(2) 0.0498(15) 0.0485(15) 0.0276(17) -0.0026(15) 0.0016(13) C4 0.116(3) 0.0360(14) 0.0497(18) 0.0069(19) -0.0055(19) 0.0025(12) C5 0.079(2) 0.0399(14) 0.0574(18) -0.0158(15) -0.0058(17) 0.0052(13) C6 0.0445(16) 0.0412(12) 0.0436(14) -0.0049(12) -0.0026(12) 0.0022(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C2 . 1.737(3) ? S1 O1 . 1.429(2) ? S1 O2 . 1.4275(19) ? S1 N1 . 1.600(2) ? S1 C1 . 1.784(2) ? N1 H11 . 0.857(19) ? N1 H12 . 0.835(18) ? C1 C6 . 1.385(4) ? C1 C2 . 1.384(4) ? C2 C3 . 1.389(4) ? C3 C4 . 1.376(5) ? C3 H3 . 0.9300 ? C4 C5 . 1.366(5) ? C4 H4 . 0.9300 ? C5 C6 . 1.393(4) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 S1 O2 . . 118.92(13) ? O1 S1 N1 . . 106.32(13) ? O2 S1 N1 . . 107.32(12) ? O1 S1 C1 . . 105.88(12) ? O2 S1 C1 . . 108.31(12) ? N1 S1 C1 . . 109.91(11) ? S1 N1 H11 . . 116(2) ? S1 N1 H12 . . 113(2) ? H11 N1 H12 . . 114(3) ? C6 C1 C2 . . 119.8(2) ? C6 C1 S1 . . 117.2(2) ? C2 C1 S1 . . 123.0(2) ? C1 C2 C3 . . 119.9(3) ? C1 C2 Cl1 . . 121.5(2) ? C3 C2 Cl1 . . 118.6(2) ? C4 C3 C2 . . 119.8(3) ? C4 C3 H3 . . 120.1 ? C2 C3 H3 . . 120.1 ? C5 C4 C3 . . 120.8(3) ? C5 C4 H4 . . 119.6 ? C3 C4 H4 . . 119.6 ? C4 C5 C6 . . 119.8(3) ? C4 C5 H5 . . 120.1 ? C6 C5 H5 . . 120.1 ? C1 C6 C5 . . 119.9(3) ? C1 C6 H6 . . 120.1 ? C5 C6 H6 . . 120.1 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 S1 C1 C6 . . . . -3.7(2) ? O2 S1 C1 C6 . . . . 124.8(2) ? N1 S1 C1 C6 . . . . -118.19(19) ? O1 S1 C1 C2 . . . . 178.5(2) ? O2 S1 C1 C2 . . . . -52.9(2) ? N1 S1 C1 C2 . . . . 64.0(2) ? C6 C1 C2 C3 . . . . 0.7(4) ? S1 C1 C2 C3 . . . . 178.4(2) ? C6 C1 C2 Cl1 . . . . 179.77(19) ? S1 C1 C2 Cl1 . . . . -2.5(3) ? C1 C2 C3 C4 . . . . -0.2(4) ? Cl1 C2 C3 C4 . . . . -179.3(2) ? C2 C3 C4 C5 . . . . -0.1(4) ? C3 C4 C5 C6 . . . . -0.1(5) ? C2 C1 C6 C5 . . . . -1.0(4) ? S1 C1 C6 C5 . . . . -178.8(2) ? C4 C5 C6 C1 . . . . 0.7(4) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H11 O1 4_554 0.857(19) 2.12(2) 2.908(3) 152(3) N1 H12 O2 4_454 0.835(18) 2.12(2) 2.941(3) 166(3)