#------------------------------------------------------------------------------ #$Date: 2011-04-07 13:44:39 +0300 (Thu, 07 Apr 2011) $ #$Revision: 17406 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2229360.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_2229360 loop_ _publ_author_name 'Shakuntala, K.' 'Foro, Sabine' 'Gowda, B. Thimme' _publ_section_title ; N-(2-Chlorophenylsulfonyl)-2-methylpropanamide ; _journal_coeditor_code DS2091 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o595 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac 'C10 H12 Cl N O3 S' _chemical_formula_moiety 'C10 H12 Cl N O3 S' _chemical_formula_sum 'C10 H12 Cl N O3 S' _chemical_formula_weight 261.72 _chemical_name_systematic ; N-(2-Chlorophenylsulfonyl)-2-methylpropanamide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 92.740(10) _cell_angle_beta 104.220(10) _cell_angle_gamma 108.750(10) _cell_formula_units_Z 2 _cell_length_a 8.3650(10) _cell_length_b 8.7190(10) _cell_length_c 9.1430(10) _cell_measurement_reflns_used 2678 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.72 _cell_measurement_theta_min 2.95 _cell_volume 606.24(13) _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 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector ; _diffrn_measurement_method ; Rotation method data acquisition using \w ; _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 0.0109 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4031 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.96 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_T_max 0.8505 _exptl_absorpt_correction_T_min 0.8136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis RED; Oxford Diffraction, 2009) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.392 _refine_diff_density_min -0.274 _refine_ls_extinction_coef 0.074(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2481 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0356 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.1796P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0987 _refine_ls_wR_factor_ref 0.1023 _reflns_number_gt 2200 _reflns_number_total 2481 _reflns_threshold_expression I>2sigma(I) _[local]_cod_data_source_file ds2091.cif _[local]_cod_data_source_block I _cod_original_cell_volume 606.24(12) _cod_database_code 2229360 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 C C1 0.8887(2) 0.33504(18) 0.17180(18) 0.0374(3) Uani d . 1 . . C C2 0.9618(2) 0.2693(2) 0.07502(19) 0.0455(4) Uani d . 1 . . C C3 1.1391(3) 0.3366(3) 0.0881(2) 0.0571(5) Uani d . 1 . . H H3 1.1882 0.2924 0.0234 0.069 Uiso calc R 1 . . C C4 1.2436(3) 0.4688(3) 0.1967(3) 0.0581(5) Uani d . 1 . . H H4 1.3630 0.5137 0.2051 0.070 Uiso calc R 1 . . C C5 1.1725(3) 0.5347(2) 0.2926(2) 0.0546(5) Uani d . 1 . . H H5 1.2436 0.6243 0.3656 0.065 Uiso calc R 1 . . C C6 0.9956(2) 0.4682(2) 0.2808(2) 0.0441(4) Uani d . 1 . . H H6 0.9477 0.5128 0.3462 0.053 Uiso calc R 1 . . C C7 0.7107(2) 0.0482(2) 0.36475(18) 0.0397(4) Uani d . 1 . . C C8 0.6623(2) -0.1303(2) 0.3835(2) 0.0481(4) Uani d . 1 . . H H8 0.5375 -0.1848 0.3306 0.058 Uiso calc R 1 . . C C9 0.6889(5) -0.1514(4) 0.5501(3) 0.0922(9) Uani d . 1 . . H H9A 0.6168 -0.1053 0.5915 0.111 Uiso calc R 1 . . H H9B 0.8101 -0.0965 0.6046 0.111 Uiso calc R 1 . . H H9C 0.6566 -0.2657 0.5599 0.111 Uiso calc R 1 . . C C10 0.7668(3) -0.2058(3) 0.3089(3) 0.0720(6) Uani d . 1 . . H H10A 0.8900 -0.1503 0.3556 0.086 Uiso calc R 1 . . H H10B 0.7401 -0.1958 0.2023 0.086 Uiso calc R 1 . . H H10C 0.7368 -0.3194 0.3215 0.086 Uiso calc R 1 . . Cl Cl1 0.83725(8) 0.10188(7) -0.06290(7) 0.0749(2) Uani d . 1 . . N N1 0.63339(19) 0.07529(16) 0.22009(16) 0.0418(3) Uani d D 1 . . H H1N 0.578(3) -0.005(2) 0.150(2) 0.050 Uiso d D 1 . . O O1 0.55713(17) 0.22202(16) 0.00990(15) 0.0571(4) Uani d . 1 . . O O2 0.63345(17) 0.36011(15) 0.27093(17) 0.0567(4) Uani d . 1 . . O O3 0.8089(2) 0.16099(17) 0.46098(15) 0.0609(4) Uani d . 1 . . S S1 0.66390(5) 0.25610(5) 0.16468(5) 0.04147(16) Uani d . 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 C1 0.0413(8) 0.0280(7) 0.0386(8) 0.0104(6) 0.0055(6) 0.0046(6) C2 0.0544(10) 0.0359(8) 0.0409(8) 0.0119(7) 0.0098(7) -0.0009(7) C3 0.0622(12) 0.0528(11) 0.0604(11) 0.0176(9) 0.0277(10) 0.0037(9) C4 0.0452(10) 0.0501(11) 0.0717(13) 0.0050(8) 0.0189(9) 0.0054(9) C5 0.0481(10) 0.0384(9) 0.0610(11) 0.0013(8) 0.0072(8) -0.0068(8) C6 0.0469(9) 0.0341(8) 0.0452(9) 0.0108(7) 0.0077(7) -0.0024(7) C7 0.0393(8) 0.0378(8) 0.0400(8) 0.0126(7) 0.0090(7) 0.0020(6) C8 0.0424(9) 0.0400(9) 0.0549(10) 0.0088(7) 0.0070(8) 0.0130(8) C9 0.118(2) 0.0910(19) 0.0757(17) 0.0331(18) 0.0383(16) 0.0458(15) C10 0.0806(16) 0.0527(12) 0.0824(16) 0.0358(12) 0.0069(12) -0.0016(11) Cl1 0.0767(4) 0.0630(4) 0.0670(4) 0.0134(3) 0.0098(3) -0.0306(3) N1 0.0444(8) 0.0286(7) 0.0412(7) 0.0055(6) 0.0017(6) 0.0008(5) O1 0.0500(7) 0.0446(7) 0.0586(8) 0.0094(6) -0.0090(6) 0.0123(6) O2 0.0506(7) 0.0399(7) 0.0824(10) 0.0184(6) 0.0210(7) 0.0004(6) O3 0.0738(9) 0.0465(7) 0.0459(7) 0.0160(7) -0.0040(6) -0.0078(6) S1 0.0381(2) 0.0302(2) 0.0493(3) 0.01005(16) 0.00256(17) 0.00424(17) 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_ _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 C6 C1 C2 . . 119.32(16) ? C6 C1 S1 . . 117.57(13) ? C2 C1 S1 . . 123.11(13) ? C3 C2 C1 . . 119.91(16) ? C3 C2 Cl1 . . 118.08(14) ? C1 C2 Cl1 . . 122.01(14) ? C4 C3 C2 . . 120.17(18) ? C4 C3 H3 . . 119.9 ? C2 C3 H3 . . 119.9 ? C5 C4 C3 . . 120.34(18) ? C5 C4 H4 . . 119.8 ? C3 C4 H4 . . 119.8 ? C4 C5 C6 . . 119.98(17) ? C4 C5 H5 . . 120.0 ? C6 C5 H5 . . 120.0 ? C5 C6 C1 . . 120.28(17) ? C5 C6 H6 . . 119.9 ? C1 C6 H6 . . 119.9 ? O3 C7 N1 . . 120.87(16) ? O3 C7 C8 . . 125.77(16) ? N1 C7 C8 . . 113.34(14) ? C7 C8 C10 . . 109.40(16) ? C7 C8 C9 . . 110.55(18) ? C10 C8 C9 . . 112.5(2) ? C7 C8 H8 . . 108.1 ? C10 C8 H8 . . 108.1 ? C9 C8 H8 . . 108.1 ? C8 C9 H9A . . 109.5 ? C8 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? C8 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? C8 C10 H10A . . 109.5 ? C8 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C8 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? C7 N1 S1 . . 124.59(11) ? C7 N1 H1N . . 119.7(15) ? S1 N1 H1N . . 115.1(14) ? O2 S1 O1 . . 118.79(9) ? O2 S1 N1 . . 109.66(8) ? O1 S1 N1 . . 104.14(8) ? O2 S1 C1 . . 107.71(8) ? O1 S1 C1 . . 110.42(8) ? N1 S1 C1 . . 105.30(8) ? 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 C1 C6 . 1.387(2) ? C1 C2 . 1.389(2) ? C1 S1 . 1.7659(17) ? C2 C3 . 1.380(3) ? C2 Cl1 . 1.7344(18) ? C3 C4 . 1.377(3) ? C3 H3 . 0.9300 ? C4 C5 . 1.371(3) ? C4 H4 . 0.9300 ? C5 C6 . 1.379(3) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? C7 O3 . 1.208(2) ? C7 N1 . 1.390(2) ? C7 C8 . 1.507(2) ? C8 C10 . 1.511(3) ? C8 C9 . 1.514(3) ? C8 H8 . 0.9800 ? C9 H9A . 0.9600 ? C9 H9B . 0.9600 ? C9 H9C . 0.9600 ? C10 H10A . 0.9600 ? C10 H10B . 0.9600 ? C10 H10C . 0.9600 ? N1 S1 . 1.6396(14) ? N1 H1N . 0.843(15) ? O1 S1 . 1.4341(13) ? O2 S1 . 1.4202(14) ? 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 H1N O1 2_655 0.843(15) 2.136(16) 2.976(2) 174(2) 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 C6 C1 C2 C3 . . . . 0.1(3) ? S1 C1 C2 C3 . . . . -179.39(15) ? C6 C1 C2 Cl1 . . . . 179.41(13) ? S1 C1 C2 Cl1 . . . . 0.0(2) ? C1 C2 C3 C4 . . . . -0.1(3) ? Cl1 C2 C3 C4 . . . . -179.50(16) ? C2 C3 C4 C5 . . . . 0.0(3) ? C3 C4 C5 C6 . . . . 0.2(3) ? C4 C5 C6 C1 . . . . -0.3(3) ? C2 C1 C6 C5 . . . . 0.1(3) ? S1 C1 C6 C5 . . . . 179.61(14) ? O3 C7 C8 C10 . . . . -101.1(2) ? N1 C7 C8 C10 . . . . 77.45(19) ? O3 C7 C8 C9 . . . . 23.2(3) ? N1 C7 C8 C9 . . . . -158.19(19) ? O3 C7 N1 S1 . . . . -0.2(2) ? C8 C7 N1 S1 . . . . -178.89(12) ? C7 N1 S1 O2 . . . . -51.29(16) ? C7 N1 S1 O1 . . . . -179.42(14) ? C7 N1 S1 C1 . . . . 64.35(16) ? C6 C1 S1 O2 . . . . 4.95(16) ? C2 C1 S1 O2 . . . . -175.59(14) ? C6 C1 S1 O1 . . . . 136.13(13) ? C2 C1 S1 O1 . . . . -44.41(16) ? C6 C1 S1 N1 . . . . -112.02(14) ? C2 C1 S1 N1 . . . . 67.44(15) ?