#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013865.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_2013865 loop_ _publ_author_name 'Howie, R. Alan' 'Low, John N.' 'Wardell, James L.' 'Glidewell, Christopher' _publ_section_title ; Hydrogen bonding in C-substituted nitroanilines: a chain of Rf̱{_3^3}(12) rings in 2-methanesulfonyl-4-nitroaniline ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o84 _journal_page_last o86 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C7 H8 N2 O4 S' _chemical_formula_moiety 'C7 H8 N2 O4 S' _chemical_formula_sum 'C7 H8 N2 O4 S' _chemical_formula_weight 216.21 _chemical_name_systematic ; 2-Methanesulfonyl-4-nitroaniline ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-I 2yc' _symmetry_space_group_name_H-M 'I 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 110.3040(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.8657(5) _cell_length_b 7.23660(10) _cell_length_c 16.4224(5) _cell_measurement_reflns_used 2026 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 3.08 _cell_volume 1768.36(8) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.005 _diffrn_reflns_av_sigmaI/netI 0.029 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 11417 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.08 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.356 _exptl_absorpt_correction_T_max 0.901 _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.30 _refine_diff_density_min -0.54 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 2026 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.100 _refine_ls_R_factor_all 0.040 _refine_ls_R_factor_gt 0.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0425P)^2^+1.6784P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.083 _refine_ls_wR_factor_ref 0.086 _reflns_number_gt 1781 _reflns_number_total 2026 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1687.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'I 2/c' _cod_database_code 2013865 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1' '-x, -y, -z' '-x, y, -z-1/2' '-x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z' 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_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 0.16472(9) -0.01648(19) 0.15027(9) 0.0129(3) Uani d . 1 C C2 0.14987(9) 0.17737(19) 0.14878(9) 0.0125(3) Uani d . 1 C C3 0.12714(9) 0.2637(2) 0.21322(9) 0.0145(3) Uani d . 1 C C4 0.11699(10) 0.1605(2) 0.27969(9) 0.0158(3) Uani d . 1 C C5 0.12723(10) -0.0314(2) 0.28184(10) 0.0179(3) Uani d . 1 C C6 0.15004(10) -0.1176(2) 0.21828(10) 0.0167(3) Uani d . 1 C N1 0.19060(9) -0.10458(17) 0.09107(8) 0.0176(3) Uani d . 1 N S2 0.15031(2) 0.31417(5) 0.06037(2) 0.01342(12) Uani d . 1 S O21 0.14908(8) 0.50435(14) 0.08577(7) 0.0217(3) Uani d . 1 O O22 0.22226(7) 0.25417(16) 0.03171(7) 0.0195(3) Uani d . 1 O C21 0.04740(10) 0.2650(2) -0.02187(10) 0.0175(3) Uani d . 1 C N4 0.09164(9) 0.2524(2) 0.34578(8) 0.0201(3) Uani d . 1 N O41 0.08705(9) 0.42239(17) 0.34441(8) 0.0302(3) Uani d . 1 O O42 0.07460(8) 0.15751(19) 0.40023(7) 0.0268(3) Uani d . 1 O H3 0.1185 0.3938 0.2117 0.017 Uiso calc R 1 H H5 0.1184 -0.1016 0.3271 0.021 Uiso calc R 1 H H6 0.1562 -0.2482 0.2197 0.020 Uiso calc R 1 H H1A 0.1985 -0.2251 0.0943 0.021 Uiso calc R 1 H H1B 0.1997 -0.0419 0.0489 0.021 Uiso calc R 1 H H21A 0.0452 0.1337 -0.0371 0.026 Uiso calc R 1 H H21B 0.0416 0.3401 -0.0732 0.026 Uiso calc R 1 H H21C -0.0021 0.2938 -0.0012 0.026 Uiso calc R 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 C1 0.0103(6) 0.0142(7) 0.0141(6) -0.0001(5) 0.0043(5) -0.0015(5) C2 0.0117(6) 0.0128(7) 0.0135(7) -0.0010(5) 0.0050(5) 0.0001(5) C3 0.0120(7) 0.0146(7) 0.0158(7) -0.0001(5) 0.0034(5) -0.0026(5) C4 0.0125(7) 0.0233(8) 0.0126(7) 0.0021(5) 0.0056(5) -0.0027(5) C5 0.0174(7) 0.0225(8) 0.0151(7) 0.0008(6) 0.0073(6) 0.0051(6) C6 0.0191(7) 0.0138(7) 0.0183(7) 0.0013(5) 0.0079(6) 0.0036(6) N1 0.0264(7) 0.0120(6) 0.0184(6) 0.0013(5) 0.0129(5) -0.0006(5) S2 0.0148(2) 0.0117(2) 0.0158(2) -0.00057(12) 0.00792(14) 0.00188(12) O21 0.0296(6) 0.0104(5) 0.0268(6) -0.0020(4) 0.0118(5) 0.0009(4) O22 0.0170(5) 0.0233(6) 0.0234(6) 0.0013(4) 0.0135(4) 0.0047(4) C21 0.0174(7) 0.0205(7) 0.0155(7) 0.0006(6) 0.0066(6) 0.0039(6) N4 0.0154(6) 0.0315(8) 0.0135(6) 0.0045(5) 0.0052(5) -0.0026(5) O41 0.0377(7) 0.0305(7) 0.0250(6) 0.0094(5) 0.0143(5) -0.0073(5) O42 0.0217(6) 0.0464(8) 0.0156(6) 0.0017(5) 0.0108(5) 0.0007(5) 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' 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 _geom_angle_publ_flag N1 C1 C6 120.02(13) no N1 C1 C2 123.20(13) no C6 C1 C2 116.77(13) no C3 C2 C1 121.30(13) no C3 C2 S2 117.06(11) no C1 C2 S2 121.43(11) no C4 C3 C2 119.71(13) no C4 C3 H3 120.1 no C2 C3 H3 120.1 no C3 C4 C5 120.95(14) no C3 C4 N4 119.06(14) no C5 C4 N4 119.93(14) no C6 C5 C4 119.54(14) no C6 C5 H5 120.2 no C4 C5 H5 120.2 no C5 C6 C1 121.62(14) no C5 C6 H6 119.2 no C1 C6 H6 119.2 no C1 N1 H1A 120.0 no C1 N1 H1B 120.0 no H1A N1 H1B 120.0 no O21 S2 O22 118.25(7) no O21 S2 C21 108.28(7) no O22 S2 C21 108.51(7) no O21 S2 C2 107.12(7) no O22 S2 C2 109.25(7) no C21 S2 C2 104.58(7) no S2 C21 H21A 109.5 no S2 C21 H21B 109.5 no H21A C21 H21B 109.5 no S2 C21 H21C 109.5 no H21A C21 H21C 109.5 no H21B C21 H21C 109.5 no O42 N4 O41 122.97(14) no O42 N4 C4 118.58(14) no O41 N4 C4 118.44(13) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.421(2) y C2 C3 1.380(2) y C3 C4 1.377(2) y C4 C5 1.397(2) y C5 C6 1.368(2) y C6 C1 1.420(2) y C1 N1 1.341(2) y C4 N4 1.444(2) y N4 O41 1.232(2) y N4 O42 1.230(2) y C2 S2 1.7592(14) y S2 O21 1.4402(11) y S2 O22 1.4443(11) y S2 C21 1.7568(15) y C3 H3 0.95 no C5 H5 0.95 no C6 H6 0.95 no N1 H1A 0.88 no N1 H1B 0.88 no C21 H21A 0.98 no C21 H21B 0.98 no C21 H21C 0.98 no 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 N1 H1A O21 1_545 0.88 2.10 2.900(2) 152 y N1 H1B O22 . 0.88 2.21 2.878(2) 133 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 _geom_torsion_publ_flag C1 C2 S2 C21 75.0(2) y C1 C2 S2 O21 -170.2(2) y C1 C2 S2 O22 -40.9(2) y C3 C4 N4 O41 -5.7(2) y C3 C4 N4 O42 173.3(2) no C5 C4 N4 O41 176.9(2) no C5 C4 N4 O42 -4.1(2) y