#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013832.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_2013832 loop_ _publ_author_name 'Nagarajan Vembu' 'Maruthai Nallu' 'Semih Durmus' 'Mathew Pazner' 'Jered Garrison' 'Wiley J. Youngs' _publ_section_title ; 2-Chlorophenyl 3-nitrobenzenesulfonate and 2,4-dichlorophenyl 3-nitrobenzenesulfonate: supramolecular aggregation through C--H···O, \p--\p and van der Waals interactions ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o65 _journal_page_last o68 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C12 H8 Cl N O5 S' _chemical_formula_moiety 'C12 H8 Cl N O5 S' _chemical_formula_sum 'C12 H8 Cl N O5 S' _chemical_formula_weight 313.70 _chemical_melting_point 368.0(10) _chemical_name_common '2-chlorophenyl m-nitrobenzenesulfonate' _chemical_name_systematic ; 2-chlorophenyl 3-nitrobenzenesulfonate ; _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 67.889(4) _cell_angle_beta 85.220(4) _cell_angle_gamma 81.617(4) _cell_formula_units_Z 2 _cell_length_a 7.4315(18) _cell_length_b 8.474(2) _cell_length_c 10.991(3) _cell_measurement_reflns_used 3667 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.30 _cell_measurement_theta_min 2.61 _cell_volume 634.1(3) _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 (Sheldrick, 1998)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.971 _diffrn_measurement_device_type 'Bruker CCD area-detector' _diffrn_measurement_method '\f and \w scans' _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 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5585 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_min 2.00 _exptl_absorpt_coefficient_mu 0.484 _exptl_absorpt_correction_T_max 0.9532 _exptl_absorpt_correction_T_min 0.8299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.464 _refine_diff_density_min -0.293 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 213 _refine_ls_number_reflns 2918 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0312 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.045P)^2^+0.2748P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0817 _refine_ls_wR_factor_ref 0.0833 _reflns_number_gt 2723 _reflns_number_total 2918 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob1154.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '367-369' was changed to '368.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '367-369' was changed to '368.0(10)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2013832 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl 0.29719(5) 0.66746(5) 0.98950(3) 0.02174(11) Uani d . 1 . . Cl S 0.27292(5) 1.07006(4) 0.65534(3) 0.01723(10) Uani d . 1 . . S O1 0.84645(17) 0.45138(14) 0.66643(12) 0.0295(3) Uani d . 1 . . O O2 0.87646(15) 0.65177(14) 0.73869(11) 0.0239(2) Uani d . 1 . . O O3 0.42172(15) 1.16492(13) 0.64187(10) 0.0225(2) Uani d . 1 . . O O4 0.11846(15) 1.14406(14) 0.57491(10) 0.0237(2) Uani d . 1 . . O O5 0.21211(14) 1.02345(13) 0.80643(10) 0.0186(2) Uani d . 1 . . O N 0.78593(18) 0.57706(16) 0.69393(12) 0.0207(3) Uani d . 1 . . N C1 0.5925(2) 0.64352(18) 0.67160(14) 0.0183(3) Uani d . 1 . . C C2 0.4783(2) 0.5454(2) 0.64478(15) 0.0221(3) Uani d . 1 . . C C3 0.2981(2) 0.6138(2) 0.61748(16) 0.0241(3) Uani d . 1 . . C C4 0.2351(2) 0.7772(2) 0.61631(15) 0.0213(3) Uani d . 1 . . C C5 0.3538(2) 0.86894(18) 0.64705(13) 0.0169(3) Uani d . 1 . . C C6 0.5345(2) 0.80422(18) 0.67521(13) 0.0170(3) Uani d . 1 . . C C7 0.0559(2) 0.94153(18) 0.85969(14) 0.0173(3) Uani d . 1 . . C C8 -0.1164(2) 1.03057(19) 0.82988(14) 0.0205(3) Uani d . 1 . . C C9 -0.2665(2) 0.9519(2) 0.89670(15) 0.0228(3) Uani d . 1 . . C C10 -0.2429(2) 0.7882(2) 0.99190(15) 0.0222(3) Uani d . 1 . . C C11 -0.0701(2) 0.6991(2) 1.02059(14) 0.0199(3) Uani d . 1 . . C C12 0.08009(19) 0.77585(19) 0.95335(14) 0.0173(3) Uani d . 1 . . C H2 0.521(3) 0.436(2) 0.6453(18) 0.021(4) Uiso d . 1 . . H H3 0.221(3) 0.553(3) 0.600(2) 0.030(5) Uiso d . 1 . . H H4 0.115(3) 0.825(2) 0.5971(19) 0.026(5) Uiso d . 1 . . H H6 0.612(2) 0.863(2) 0.6956(18) 0.020(4) Uiso d . 1 . . H H8 -0.127(3) 1.144(3) 0.767(2) 0.030(5) Uiso d . 1 . . H H9 -0.379(3) 1.011(3) 0.8785(19) 0.027(5) Uiso d . 1 . . H H10 -0.345(3) 0.739(2) 1.0401(19) 0.027(5) Uiso d . 1 . . H H11 -0.054(2) 0.593(2) 1.0845(18) 0.021(4) 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 Cl 0.01686(18) 0.02233(19) 0.02012(18) 0.00041(13) -0.00189(13) -0.00192(14) S 0.02130(19) 0.01569(17) 0.01299(17) -0.00208(13) -0.00070(13) -0.00342(13) O1 0.0313(6) 0.0213(6) 0.0329(6) 0.0034(5) 0.0014(5) -0.0096(5) O2 0.0217(5) 0.0254(6) 0.0216(5) -0.0035(4) -0.0025(4) -0.0047(4) O3 0.0287(6) 0.0181(5) 0.0196(5) -0.0069(4) 0.0016(4) -0.0045(4) O4 0.0258(6) 0.0236(5) 0.0171(5) 0.0023(4) -0.0037(4) -0.0035(4) O5 0.0222(5) 0.0198(5) 0.0141(5) -0.0044(4) 0.0004(4) -0.0059(4) N 0.0234(6) 0.0175(6) 0.0159(6) -0.0013(5) 0.0013(5) -0.0011(5) C1 0.0205(7) 0.0185(7) 0.0136(6) -0.0027(5) 0.0011(5) -0.0036(5) C2 0.0286(8) 0.0188(7) 0.0196(7) -0.0058(6) 0.0040(6) -0.0079(6) C3 0.0253(8) 0.0259(8) 0.0264(8) -0.0106(6) 0.0021(6) -0.0136(6) C4 0.0197(7) 0.0259(8) 0.0190(7) -0.0053(6) 0.0006(6) -0.0086(6) C5 0.0207(7) 0.0169(6) 0.0124(6) -0.0037(5) 0.0020(5) -0.0048(5) C6 0.0204(7) 0.0183(7) 0.0124(6) -0.0060(5) 0.0004(5) -0.0044(5) C7 0.0204(7) 0.0190(7) 0.0141(6) -0.0027(5) 0.0006(5) -0.0081(5) C8 0.0252(8) 0.0190(7) 0.0169(7) 0.0029(6) -0.0027(6) -0.0077(6) C9 0.0190(7) 0.0297(8) 0.0222(7) 0.0032(6) -0.0043(6) -0.0140(6) C10 0.0191(7) 0.0303(8) 0.0209(7) -0.0056(6) 0.0016(6) -0.0133(6) C11 0.0219(7) 0.0211(7) 0.0162(7) -0.0036(6) -0.0007(6) -0.0061(6) C12 0.0171(7) 0.0195(7) 0.0154(6) 0.0007(5) -0.0027(5) -0.0072(5) 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 Cl C12 . 1.7334(15) y S O3 . 1.4259(12) y S O4 . 1.4263(11) y S O5 . 1.5972(11) y S C5 . 1.7560(15) y O1 N . 1.2279(17) y O2 N . 1.2285(17) y O5 C7 . 1.4099(17) y N C1 . 1.471(2) y C1 C6 . 1.381(2) ? C1 C2 . 1.389(2) ? C2 C3 . 1.389(2) ? C2 H2 . 0.931(19) ? C3 C4 . 1.392(2) ? C3 H3 . 0.90(2) ? C4 C5 . 1.394(2) ? C4 H4 . 0.93(2) ? C5 C6 . 1.388(2) ? C6 H6 . 0.909(19) ? C7 C8 . 1.385(2) ? C7 C12 . 1.390(2) ? C8 C9 . 1.393(2) ? C8 H8 . 0.95(2) ? C9 C10 . 1.385(2) ? C9 H9 . 0.90(2) ? C10 C11 . 1.387(2) ? C10 H10 . 0.94(2) ? C11 C12 . 1.388(2) ? C11 H11 . 0.910(19) ? 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' Cl Cl 0.1484 0.1585 '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 S O4 120.68(7) y O3 S O5 102.60(6) y O4 S O5 109.87(6) y O3 S C5 109.71(7) y O4 S C5 109.31(7) y O5 S C5 103.13(6) y C7 O5 S 121.60(9) y O1 N O2 124.34(14) y O1 N C1 118.10(13) y O2 N C1 117.55(13) y C6 C1 C2 123.19(14) ? C6 C1 N 117.62(13) ? C2 C1 N 119.16(13) ? C3 C2 C1 118.40(14) ? C3 C2 H2 120.8(12) ? C1 C2 H2 120.8(12) ? C2 C3 C4 120.36(14) ? C2 C3 H3 120.3(13) ? C4 C3 H3 119.4(13) ? C3 C4 C5 119.08(15) ? C3 C4 H4 121.2(12) ? C5 C4 H4 119.7(12) ? C6 C5 C4 122.01(14) ? C6 C5 S 118.36(11) ? C4 C5 S 119.61(12) ? C1 C6 C5 116.92(14) ? C1 C6 H6 120.7(11) ? C5 C6 H6 122.4(11) ? C8 C7 C12 121.09(14) ? C8 C7 O5 120.59(13) ? C12 C7 O5 117.96(13) ? C7 C8 C9 118.80(14) ? C7 C8 H8 118.6(12) ? C9 C8 H8 122.6(12) ? C10 C9 C8 120.30(14) ? C10 C9 H9 121.1(12) ? C8 C9 H9 118.6(12) ? C9 C10 C11 120.64(15) ? C9 C10 H10 119.3(12) ? C11 C10 H10 120.0(12) ? C10 C11 C12 119.40(14) ? C10 C11 H11 120.6(12) ? C12 C11 H11 120.0(12) ? C11 C12 C7 119.76(13) ? C11 C12 Cl 120.00(11) ? C7 C12 Cl 120.21(12) ? 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 C2 H2 O1 . 0.931(19) 2.472(18) 2.740(2) 96.6(13) y C4 H4 O4 . 0.93(2) 2.626(19) 2.973(2) 102.8(13) y C6 H6 O2 . 0.909(19) 2.404(18) 2.6968(19) 98.8(13) y C6 H6 O3 . 0.909(19) 2.615(18) 2.9396(19) 101.9(13) y C8 H8 O4 . 0.95(2) 2.67(2) 3.0772(19) 106.4(14) y C2 H2 O3 1_545 0.931(19) 2.531(19) 3.324(2) 143.2(15) y C4 H4 O2 1_455 0.93(2) 2.511(19) 3.033(2) 115.7(14) y C3 H3 O1 1_455 0.90(2) 2.99(2) 3.733(2) 141.9(16) y C9 H9 O3 1_455 0.90(2) 2.86(2) 3.539(2) 132.8(15) y C4 H4 O4 2_576 0.93(2) 2.59(2) 3.335(2) 137.6(15) y C8 H8 O1 1_465 0.95(2) 2.40(2) 3.316(2) 162.5(16) y C11 H11 O2 2_667 0.910(19) 2.532(19) 3.3726(19) 153.8(15) 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 O3 S O5 C7 174.16(10) ? O4 S O5 C7 44.62(12) ? C5 S O5 C7 -71.82(11) y O1 N C1 C6 -166.26(13) ? O2 N C1 C6 13.55(19) ? O1 N C1 C2 12.1(2) ? O2 N C1 C2 -168.09(13) ? C6 C1 C2 C3 1.4(2) ? N C1 C2 C3 -176.83(13) ? C1 C2 C3 C4 0.5(2) ? C2 C3 C4 C5 -2.1(2) ? C3 C4 C5 C6 1.9(2) ? C3 C4 C5 S -176.31(12) ? O3 S C5 C6 21.99(13) ? O4 S C5 C6 156.39(11) ? O5 S C5 C6 -86.76(12) ? O3 S C5 C4 -159.78(11) ? O4 S C5 C4 -25.38(14) ? O5 S C5 C4 91.47(12) ? C2 C1 C6 C5 -1.6(2) ? N C1 C6 C5 176.66(12) ? C4 C5 C6 C1 -0.1(2) ? S C5 C6 C1 178.13(10) ? S O5 C7 C8 -73.02(15) ? S O5 C7 C12 113.84(13) ? C12 C7 C8 C9 0.7(2) ? O5 C7 C8 C9 -172.21(13) ? C7 C8 C9 C10 0.6(2) ? C8 C9 C10 C11 -1.1(2) ? C9 C10 C11 C12 0.3(2) ? C10 C11 C12 C7 0.9(2) ? C10 C11 C12 Cl 179.15(11) ? C8 C7 C12 C11 -1.5(2) ? O5 C7 C12 C11 171.64(12) ? C8 C7 C12 Cl -179.69(11) ? O5 C7 C12 Cl -6.57(18) ?