#------------------------------------------------------------------------------ #$Date: 2016-02-20 16:35:30 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176787 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/43/2214336.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_2214336 loop_ _publ_author_name 'B. Thimme Gowda' 'Sabine Foro' 'Hartmut Fuess' _publ_section_title ; N-(2,3-Dichlorophenyl)methanesulfonamide ; _journal_coeditor_code LW2022 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3086 _journal_page_last o3086 _journal_paper_doi 10.1107/S160053680702555X _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C7 H7 Cl2 N O2 S' _chemical_formula_moiety 'C7 H7 Cl2 N O2 S' _chemical_formula_sum 'C7 H7 Cl2 N O2 S' _chemical_formula_weight 240.10 _chemical_name_common Methanesulfon-2,3-dichloroanilide _chemical_name_systematic ; N-(2,3-dichlorophenyl)methanesulfonamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.038(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.1299(9) _cell_length_b 5.1365(6) _cell_length_c 16.9080(10) _cell_measurement_reflns_used 2484 _cell_measurement_temperature 303(2) _cell_measurement_theta_max 26.49 _cell_measurement_theta_min 2.79 _cell_volume 966.61(15) _computing_cell_refinement 'CrysAlis CCD' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2003)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2003)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 303(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _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 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 5750 _diffrn_reflns_theta_full 26.35 _diffrn_reflns_theta_max 26.35 _diffrn_reflns_theta_min 4.15 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.851 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'long prism' _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.572 _refine_diff_density_min -0.706 _refine_ls_extinction_coef 0.016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 0.866 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 122 _refine_ls_number_reflns 1939 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.866 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0536 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1248P)^2^+0.7632P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1460 _refine_ls_wR_factor_ref 0.1517 _reflns_number_gt 1694 _reflns_number_total 1939 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lw2022.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2214336 _cod_database_fobs_code 2214336 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 C C1 0.1880(4) 0.2088(7) -0.08851(19) 0.0657(10) Uani d . 1 H H1A 0.1995 0.1405 -0.1408 0.099 Uiso calc R 1 H H1B 0.2505 0.3317 -0.0768 0.099 Uiso calc R 1 H H1C 0.1114 0.2940 -0.0855 0.099 Uiso calc R 1 C C6 0.2632(2) 0.2694(5) 0.10012(14) 0.0341(5) Uani d . 1 C C7 0.3847(3) 0.2686(6) 0.08165(17) 0.0439(6) Uani d . 1 H H7 0.4140 0.1514 0.0444 0.053 Uiso calc R 1 C C8 0.4626(3) 0.4409(6) 0.1182(2) 0.0520(8) Uani d . 1 H H8 0.5438 0.4368 0.1054 0.062 Uiso calc R 1 C C9 0.4221(3) 0.6189(6) 0.17337(18) 0.0485(7) Uani d . 1 H H9 0.4750 0.7356 0.1970 0.058 Uiso calc R 1 C C10 0.3017(3) 0.6200(5) 0.19266(15) 0.0382(6) Uani d . 1 C C11 0.2221(2) 0.4472(5) 0.15705(14) 0.0324(5) Uani d . 1 Cl Cl12 0.07252(6) 0.44392(16) 0.18443(4) 0.0490(3) Uani d . 1 Cl Cl13 0.24995(7) 0.84109(15) 0.26233(4) 0.0517(3) Uani d . 1 N N5 0.1792(2) 0.0930(5) 0.06667(14) 0.0425(6) Uani d . 1 H H5N 0.107(3) 0.137(6) 0.077(2) 0.051 Uiso d . 1 O O3 0.0884(2) -0.2047(4) -0.02830(14) 0.0581(6) Uani d . 1 O O4 0.3061(2) -0.1694(4) -0.02436(14) 0.0543(6) Uani d . 1 S S2 0.19291(6) -0.04550(12) -0.02004(4) 0.0371(3) 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 0.106(3) 0.0489(17) 0.0418(16) 0.0056(18) -0.0132(18) 0.0018(14) C6 0.0320(12) 0.0386(12) 0.0318(11) 0.0000(10) -0.0014(9) -0.0023(10) C7 0.0360(14) 0.0521(16) 0.0437(14) 0.0054(11) 0.0032(11) -0.0111(12) C8 0.0297(14) 0.067(2) 0.0591(19) 0.0001(12) 0.0020(13) -0.0091(15) C9 0.0394(15) 0.0577(17) 0.0485(17) -0.0056(13) -0.0093(12) -0.0050(13) C10 0.0453(14) 0.0405(13) 0.0288(12) 0.0036(11) -0.0034(10) -0.0032(10) C11 0.0302(12) 0.0393(13) 0.0276(11) 0.0039(9) -0.0001(9) 0.0024(9) Cl12 0.0334(4) 0.0687(5) 0.0449(5) 0.0027(3) 0.0076(3) -0.0140(3) Cl13 0.0633(5) 0.0521(5) 0.0395(4) 0.0029(3) -0.0015(3) -0.0138(3) N5 0.0334(12) 0.0530(13) 0.0412(12) -0.0036(10) 0.0063(10) -0.0162(10) O3 0.0481(12) 0.0551(12) 0.0711(15) -0.0108(10) 0.0010(10) -0.0263(11) O4 0.0479(12) 0.0562(12) 0.0588(13) 0.0178(10) -0.0010(10) -0.0168(10) S2 0.0386(4) 0.0353(4) 0.0373(4) 0.0039(2) -0.0014(3) -0.0079(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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle S2 C1 H1A 109.5 S2 C1 H1B 109.5 H1A C1 H1B 109.5 S2 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 C7 C6 C11 118.3(2) C7 C6 N5 123.4(2) C11 C6 N5 118.3(2) C6 C7 C8 120.5(3) C6 C7 H7 119.8 C8 C7 H7 119.8 C9 C8 C7 121.3(3) C9 C8 H8 119.3 C7 C8 H8 119.3 C8 C9 C10 118.6(3) C8 C9 H9 120.7 C10 C9 H9 120.7 C11 C10 C9 120.9(2) C11 C10 Cl13 120.0(2) C9 C10 Cl13 119.1(2) C10 C11 C6 120.3(2) C10 C11 Cl12 120.22(19) C6 C11 Cl12 119.45(19) C6 N5 S2 124.90(19) C6 N5 H5N 112(2) S2 N5 H5N 113(2) O4 S2 O3 117.55(14) O4 S2 N5 109.03(13) O3 S2 N5 105.07(12) O4 S2 C1 109.26(18) O3 S2 C1 109.79(18) N5 S2 C1 105.41(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 S2 1.746(3) C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600 C6 C7 1.388(4) C6 C11 1.404(3) C6 N5 1.420(3) C7 C8 1.384(4) C7 H7 0.9300 C8 C9 1.382(4) C8 H8 0.9300 C9 C10 1.380(4) C9 H9 0.9300 C10 C11 1.390(4) C10 Cl13 1.735(3) C11 Cl12 1.729(3) N5 S2 1.637(2) N5 H5N 0.86(4) O3 S2 1.428(2) O4 S2 1.413(2) 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 N5 H5N O3 3 0.86(4) 2.35(4) 3.101(3) 147(3) N5 H5N Cl12 . 0.86(4) 2.43(3) 2.937(2) 118(3) 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 C11 C6 C7 C8 -0.6(4) N5 C6 C7 C8 -178.0(3) C6 C7 C8 C9 -0.4(5) C7 C8 C9 C10 1.0(5) C8 C9 C10 C11 -0.5(4) C8 C9 C10 Cl13 179.6(2) C9 C10 C11 C6 -0.5(4) Cl13 C10 C11 C6 179.42(19) C9 C10 C11 Cl12 177.8(2) Cl13 C10 C11 Cl12 -2.3(3) C7 C6 C11 C10 1.0(4) N5 C6 C11 C10 178.6(2) C7 C6 C11 Cl12 -177.3(2) N5 C6 C11 Cl12 0.3(3) C7 C6 N5 S2 -27.1(4) C11 C6 N5 S2 155.4(2) C6 N5 S2 O4 53.1(3) C6 N5 S2 O3 179.9(2) C6 N5 S2 C1 -64.1(3)