#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202468.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_2202468 loop_ _publ_author_name 'Vembu, Nagarajan' 'Nallu, Maruthai' 'Spencer, Elinor C.' 'Howard, Judith A. K.' _publ_section_title ; 3-Nitrobenzenesulfonyl chloride: molecular aggregation through C---H···O interactions ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1036 _journal_page_last o1038 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C6 H4 Cl N O4 S' _chemical_formula_moiety 'C6 H4 Cl N O4 S' _chemical_formula_sum 'C6 H4 Cl N O4 S' _chemical_formula_weight 221.61 _chemical_melting_point 334.0(10) _chemical_name_common 'm-nitrobenzenesulfonyl chloride' _chemical_name_systematic ; 3-Nitrobenzenesulfonyl chloride ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 107.318(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.8868(4) _cell_length_b 9.4298(4) _cell_length_c 11.8789(5) _cell_measurement_reflns_used 823 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.4705 _cell_measurement_theta_min 2.7655 _cell_volume 843.40(7) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1998)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD 6K area-detector' _diffrn_measurement_method \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 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9420 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.77 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.679 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_correction_T_min 0.822 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _refine_diff_density_max 1.263 _refine_diff_density_min -0.689 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 134 _refine_ls_number_reflns 1928 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0392 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.053P)^2^+0.872P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1015 _refine_ls_wR_factor_ref 0.1057 _reflns_number_gt 1667 _reflns_number_total 1928 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6235.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '333-335 K' was changed to '334.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202468 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _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_occupancy _atom_site_type_symbol Cl1 0.32306(8) 0.43025(6) 0.53772(6) 0.03728(19) Uani d 1 Cl S1 0.10523(7) 0.30523(5) 0.49511(4) 0.02122(16) Uani d 1 S O1 0.3023(3) -0.28186(18) 0.32733(16) 0.0359(4) Uani d 1 O O2 0.1028(3) -0.13592(19) 0.22689(15) 0.0386(4) Uani d 1 O O3 0.0254(2) 0.32696(18) 0.58608(16) 0.0316(4) Uani d 1 O O4 0.0094(3) 0.3315(2) 0.37543(16) 0.0410(5) Uani d 1 O N1 0.2148(3) -0.17316(19) 0.31766(16) 0.0248(4) Uani d 1 N C1 0.2439(3) -0.0821(2) 0.42233(18) 0.0203(4) Uani d 1 C C2 0.3410(3) -0.1353(2) 0.5311(2) 0.0244(4) Uani d 1 C C3 0.3635(3) -0.0513(2) 0.6308(2) 0.0271(5) Uani d 1 C C4 0.2911(3) 0.0838(2) 0.61985(19) 0.0247(5) Uani d 1 C C5 0.1983(3) 0.1340(2) 0.50833(18) 0.0190(4) Uani d 1 C C6 0.1716(3) 0.0529(2) 0.40713(18) 0.0194(4) Uani d 1 C H2 0.386(4) -0.224(3) 0.540(2) 0.026(6) Uiso d 1 H H3 0.429(4) -0.082(3) 0.706(3) 0.040(8) Uiso d 1 H H4 0.303(3) 0.139(3) 0.685(2) 0.025(6) Uiso d 1 H H6 0.108(4) 0.086(3) 0.330(2) 0.026(6) Uiso d 1 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 Cl1 0.0286(3) 0.0218(3) 0.0638(4) -0.0036(2) 0.0174(3) -0.0001(3) S1 0.0207(3) 0.0197(3) 0.0215(3) 0.00173(19) 0.0036(2) -0.00229(18) O1 0.0443(10) 0.0287(9) 0.0386(10) 0.0089(8) 0.0183(8) -0.0060(7) O2 0.0581(12) 0.0280(9) 0.0229(8) 0.0007(8) 0.0015(8) -0.0050(7) O3 0.0325(9) 0.0284(9) 0.0398(10) -0.0031(7) 0.0194(8) -0.0083(7) O4 0.0527(12) 0.0318(9) 0.0266(9) 0.0173(8) -0.0064(8) -0.0034(7) N1 0.0318(10) 0.0220(9) 0.0230(9) -0.0032(7) 0.0117(8) -0.0015(7) C1 0.0210(10) 0.0192(10) 0.0216(10) -0.0028(8) 0.0077(8) -0.0022(8) C2 0.0245(10) 0.0192(11) 0.0286(11) 0.0008(8) 0.0067(9) 0.0028(8) C3 0.0310(12) 0.0247(11) 0.0210(10) 0.0008(9) 0.0010(9) 0.0034(8) C4 0.0279(11) 0.0249(11) 0.0186(10) -0.0009(8) 0.0027(8) -0.0015(8) C5 0.0189(9) 0.0172(10) 0.0200(9) 0.0004(7) 0.0043(7) 0.0008(7) C6 0.0189(10) 0.0211(10) 0.0174(9) -0.0015(8) 0.0044(8) 0.0016(7) 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' 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' Cl Cl 0.1484 0.1585 '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' 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 O3 S1 O4 120.87(12) y O3 S1 C5 109.41(10) y O4 S1 C5 109.45(10) y O3 S1 Cl1 105.20(8) y O4 S1 Cl1 107.98(10) y C5 S1 Cl1 102.24(7) y O1 N1 O2 124.23(19) y O1 N1 C1 117.94(18) y O2 N1 C1 117.83(18) y C6 C5 C4 122.58(19) ? C6 C5 S1 118.46(15) ? C4 C5 S1 118.93(16) ? C6 C1 C2 123.1(2) ? C6 C1 N1 118.14(18) ? C2 C1 N1 118.73(19) ? C1 C6 C5 116.33(19) ? C1 C6 H6 120.5(16) ? C5 C6 H6 123.2(16) ? C4 C3 C2 119.9(2) ? C4 C3 H3 118.2(19) ? C2 C3 H3 121.9(19) ? C3 C4 C5 119.2(2) ? C3 C4 H4 120.6(16) ? C5 C4 H4 120.2(16) ? C1 C2 C3 118.9(2) ? C1 C2 H2 122.4(18) ? C3 C2 H2 118.6(17) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O3 1.4182(17) y S1 O4 1.4193(18) y S1 C5 1.761(2) y S1 Cl1 2.0198(8) y O1 N1 1.222(3) y N1 O2 1.224(3) y N1 C1 1.472(3) y C5 C6 1.387(3) y C5 C4 1.392(3) y C1 C6 1.384(3) y C1 C2 1.385(3) y C6 H6 0.95(3) ? C3 C4 1.386(3) y C3 C2 1.391(3) y C3 H3 0.93(3) ? C4 H4 0.91(3) ? C2 H2 0.90(3) ? 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 _geom_hbond_publ_flag C6 H6 O4 . 0.95(3) 2.55(3) 2.897(3) 101.9(18) y C6 H6 O2 . 0.95(3) 2.42(3) 2.712(3) 97.1(18) y C4 H4 O3 . 0.91(3) 2.79(3) 3.051(3) 97.8(18) y C2 H2 O1 . 0.90(3) 2.48(3) 2.725(3) 96.0(19) y C4 H4 O4 4_666 0.91(3) 2.38(3) 3.116(3) 138(2) y C6 H6 O1 2 0.95(3) 2.52(3) 3.251(3) 134(2) y C3 H3 O2 4_656 0.93(3) 2.97(3) 3.504(3) 118(2) y C2 H2 O2 4_656 0.90(3) 2.71(3) 3.387(3) 133(2) y C3 H3 O3 2_546 0.93(3) 2.54(3) 3.412(3) 156(3) y 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 O3 S1 C5 C6 135.78(17) O4 S1 C5 C6 1.2(2) Cl1 S1 C5 C6 -113.06(16) O3 S1 C5 C4 -42.4(2) O4 S1 C5 C4 -176.90(18) Cl1 S1 C5 C4 68.79(18) O1 N1 C1 C6 167.96(19) O2 N1 C1 C6 -12.9(3) O1 N1 C1 C2 -12.5(3) O2 N1 C1 C2 166.6(2) C2 C1 C6 C5 -1.1(3) N1 C1 C6 C5 178.45(18) C4 C5 C6 C1 -0.6(3) S1 C5 C6 C1 -178.63(15) C2 C3 C4 C5 -0.7(3) C6 C5 C4 C3 1.5(3) S1 C5 C4 C3 179.53(17) C6 C1 C2 C3 1.8(3) N1 C1 C2 C3 -177.8(2) C4 C3 C2 C1 -0.8(3)