#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/43/2214386.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_2214386 loop_ _publ_author_name 'Qing-An Wu' 'Wei-Ming Fang' 'Da-Wei Luo' 'Zhen-Yuan Xu' _publ_section_title ; 1-Methyl-4-methylsulfonyl-2-nitrobenzene ; _journal_coeditor_code SG2167 _journal_issue 7 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3320 _journal_page_last o3320 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C8 H9 N O4 S' _chemical_formula_moiety 'C8 H9 N O4 S' _chemical_formula_sum 'C8 H9 N O4 S' _chemical_formula_weight 215.22 _chemical_name_systematic ; 1-Methyl-4-methylsulfonyl-2-nitrobenzene ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_formula_units_Z 4 _cell_length_a 14.957(11) _cell_length_b 8.268(5) _cell_length_c 7.795(5) _cell_measurement_reflns_used 7747 _cell_measurement_temperature 298.0(10) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.6 _cell_volume 964.1(11) _computing_cell_refinement PROCESS-AUTO _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1993)' _diffrn_detector_area_resol_mean 10.00 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 8883 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_T_max 0.893 _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_description chunk _exptl_crystal_F_000 448.00 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.23 _refine_diff_density_min -0.31 _refine_ls_abs_structure_details 'Flack (1983), 927 Friedel pairs' _refine_ls_abs_structure_Flack 0.002(8) _refine_ls_extinction_coef 78(10) _refine_ls_extinction_method 'Larson (1970), equation 22' _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 129 _refine_ls_number_reflns 2109 _refine_ls_R_factor_gt 0.0325 _refine_ls_shift/su_max 0.0000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[0.0001Fo^2^ + \s(Fo^2^)]/(4Fo^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0770 _reflns_number_gt 1430 _reflns_number_total 2109 _reflns_threshold_expression F^2^>2\s(F^2^) _[local]_cod_data_source_file sg2167.cif loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,+Y,1/2+Z 3 1/2+X,-Y,+Z 4 -X,-Y,1/2+Z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, 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 S S1 0.14758(4) 0.09312(6) 0.41547(12) 0.04659(16) Uani d . 1.00 O O1 0.48784(12) 0.2707(2) 0.4356(3) 0.0711(6) Uani d . 1.00 O O2 0.48852(12) 0.4559(2) 0.6321(2) 0.0735(7) Uani d . 1.00 O O3 0.07388(12) 0.1408(2) 0.3105(2) 0.0659(6) Uani d . 1.00 O O4 0.20666(12) -0.02992(19) 0.3535(2) 0.0663(6) Uani d . 1.00 N N1 0.45069(14) 0.3727(2) 0.5241(3) 0.0530(7) Uani d . 1.00 C C1 0.21356(14) 0.2679(2) 0.4542(3) 0.0403(6) Uani d . 1.00 C C2 0.30390(16) 0.2549(2) 0.4770(2) 0.0419(7) Uani d . 1.00 C C3 0.35365(14) 0.3938(2) 0.5021(2) 0.0424(6) Uani d . 1.00 C C4 0.31618(18) 0.5478(2) 0.5019(3) 0.0504(8) Uani d . 1.00 C C5 0.2253(2) 0.5549(3) 0.4783(4) 0.0609(9) Uani d . 1.00 C C6 0.17398(16) 0.4192(3) 0.4536(3) 0.0581(9) Uani d . 1.00 C C7 0.3700(2) 0.7023(3) 0.5207(4) 0.0733(10) Uani d . 1.00 C C8 0.1062(2) 0.0349(3) 0.6141(3) 0.0690(10) Uani d . 1.00 H H2 0.3315 0.1541 0.4756 0.050 Uiso c R 1.00 H H5 0.1974 0.6554 0.4792 0.073 Uiso c R 1.00 H H6 0.1127 0.4290 0.4365 0.070 Uiso c R 1.00 H H71 0.3851 0.7181 0.6392 0.088 Uiso c R 1.00 H H72 0.4238 0.6941 0.4541 0.088 Uiso c R 1.00 H H73 0.3352 0.7922 0.4808 0.088 Uiso c R 1.00 H H81 0.0782 0.1258 0.6686 0.083 Uiso c R 1.00 H H82 0.0631 -0.0500 0.5990 0.083 Uiso c R 1.00 H H83 0.1545 -0.0034 0.6844 0.083 Uiso c R 1.00 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 S1 0.0413(3) 0.0524(3) 0.0461(3) -0.0051(2) -0.0017(3) -0.0033(4) O1 0.0432(10) 0.0778(12) 0.0924(17) 0.0151(9) 0.0107(13) -0.0011(14) O2 0.0488(12) 0.0821(16) 0.0896(17) -0.0209(11) -0.0162(12) -0.0064(13) O3 0.0552(12) 0.0772(12) 0.0652(13) -0.0104(10) -0.0213(10) 0.0067(11) O4 0.0604(13) 0.0469(9) 0.0916(17) -0.0024(9) 0.0119(10) -0.0192(10) N1 0.0408(12) 0.0589(15) 0.0592(15) -0.0022(11) 0.0029(11) 0.0176(12) C1 0.0359(12) 0.0442(13) 0.0408(16) 0.0015(10) 0.0013(11) 0.0024(11) C2 0.0424(15) 0.0401(13) 0.0431(15) 0.0035(10) 0.0045(11) 0.0012(11) C3 0.0328(12) 0.0478(14) 0.0464(13) 0.0007(11) 0.0009(11) 0.0023(12) C4 0.0518(16) 0.0462(15) 0.0532(16) -0.0002(12) -0.0001(13) 0.0039(12) C5 0.0508(16) 0.0472(15) 0.085(2) 0.0113(13) -0.0065(14) -0.0078(14) C6 0.0395(14) 0.0574(15) 0.077(2) 0.0077(12) -0.0054(13) -0.0051(15) C7 0.070(2) 0.0471(16) 0.103(2) -0.0069(15) -0.0101(19) -0.0022(17) C8 0.0611(19) 0.094(2) 0.0516(17) -0.0259(17) 0.0001(15) 0.0019(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O3 1.428(2) S1 O4 1.4316(18) S1 C1 1.776(2) S1 C8 1.735(2) O1 N1 1.223(3) O2 N1 1.226(3) N1 C3 1.472(3) C1 C2 1.367(3) C1 C6 1.384(3) C2 C3 1.383(3) C3 C4 1.391(3) C4 C5 1.373(4) C4 C7 1.517(3) C5 C6 1.373(3) C2 H2 0.930 C5 H5 0.930 C6 H6 0.930 C7 H71 0.960 C7 H72 0.960 C7 H73 0.960 C8 H81 0.960 C8 H82 0.960 C8 H83 0.960 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O3 S1 O4 118.64(13) O3 S1 C1 107.56(11) O3 S1 C8 108.20(13) O4 S1 C1 107.02(10) O4 S1 C8 108.91(13) C1 S1 C8 105.78(13) O1 N1 O2 124.4(2) O1 N1 C3 117.7(2) O2 N1 C3 117.9(2) S1 C1 C2 120.50(17) S1 C1 C6 119.82(17) C2 C1 C6 119.6(2) C1 C2 C3 119.0(2) N1 C3 C2 116.7(2) N1 C3 C4 120.4(2) C2 C3 C4 122.9(2) C3 C4 C5 116.0(2) C3 C4 C7 123.8(2) C5 C4 C7 120.2(2) C4 C5 C6 122.5(2) C1 C6 C5 119.9(2) C1 C2 H2 120.5 C3 C2 H2 120.5 C4 C5 H5 118.8 C6 C5 H5 118.8 C1 C6 H6 120.0 C5 C6 H6 120.0 C4 C7 H71 109.5 C4 C7 H72 109.5 C4 C7 H73 109.5 H71 C7 H72 109.5 H71 C7 H73 109.5 H72 C7 H73 109.5 S1 C8 H81 109.5 S1 C8 H82 109.5 S1 C8 H83 109.5 H81 C8 H82 109.5 H81 C8 H83 109.5 H82 C8 H83 109.5 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 C1 C2 -149.2(2) O3 S1 C1 C6 27.8(2) O4 S1 C1 C2 -20.7(2) O4 S1 C1 C6 156.3(2) C8 S1 C1 C2 95.3(2) C8 S1 C1 C6 -87.7(2) O1 N1 C3 C2 38.9(3) O1 N1 C3 C4 -139.2(2) O2 N1 C3 C2 -139.7(2) O2 N1 C3 C4 42.2(3) S1 C1 C2 C3 178.19(18) S1 C1 C6 C5 -178.0(2) C2 C1 C6 C5 -1.0(4) C6 C1 C2 C3 1.2(3) C1 C2 C3 N1 -179.4(2) C1 C2 C3 C4 -1.4(3) N1 C3 C4 C5 179.2(2) N1 C3 C4 C7 1.0(3) C2 C3 C4 C5 1.3(3) C2 C3 C4 C7 -177.0(2) C3 C4 C5 C6 -1.0(4) C7 C4 C5 C6 177.3(2) C4 C5 C6 C1 0.9(4) _cod_database_code 2214386