#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013833.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_2013833 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_paper_doi 10.1107/S0108270103027380 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C12 H7 Cl2 N O5 S' _chemical_formula_moiety 'C12 H7 Cl2 N O5 S' _chemical_formula_sum 'C12 H7 Cl2 N O5 S' _chemical_formula_weight 348.15 _chemical_melting_point 366.5(5) _chemical_name_systematic ; 2,4-Dichlorophenyl 3-nitrobenzenesulfonate ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.878(5) _cell_length_b 13.330(10) _cell_length_c 14.990(11) _cell_measurement_reflns_used 7544 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.30 _cell_measurement_theta_min 2.72 _cell_volume 1374.3(18) _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 0.971 _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 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 11316 _diffrn_reflns_theta_full 28.38 _diffrn_reflns_theta_max 28.38 _diffrn_reflns_theta_min 2.04 _exptl_absorpt_coefficient_mu 0.644 _exptl_absorpt_correction_T_max 0.8303 _exptl_absorpt_correction_T_min 0.7390 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.380 _refine_diff_density_min -0.283 _refine_ls_abs_structure_details 'Flack (1983), 1283 Friedel pairs' _refine_ls_abs_structure_Flack 0.02(6) _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 218 _refine_ls_number_reflns 3268 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0321 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.0813 _reflns_number_gt 3158 _reflns_number_total 3268 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob1154.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 '366-367' was changed to '366.5(5)' - 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 '366-367' was changed to '366.5(5)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_original_cell_volume 1374.3(17) _cod_database_code 2013833 _cod_database_fobs_code 2013833 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 0.37528(8) 0.72585(4) 1.16297(4) 0.03515(14) Uani d . 1 . . Cl Cl2 0.70015(8) 0.36113(4) 1.12658(4) 0.03054(13) Uani d . 1 . . Cl S1 1.11206(7) 0.46106(4) 0.96706(3) 0.02198(12) Uani d . 1 . . S N1 0.4809(3) 0.53990(16) 0.79536(12) 0.0313(4) Uani d . 1 . . N O1 0.3376(3) 0.51043(15) 0.75540(11) 0.0438(5) Uani d . 1 . . O O2 0.5212(3) 0.62900(13) 0.80680(12) 0.0405(4) Uani d . 1 . . O O3 1.1685(2) 0.55771(11) 0.93622(10) 0.0288(3) Uani d . 1 . . O O4 1.2483(2) 0.38069(11) 0.97053(11) 0.0312(3) Uani d . 1 . . O O5 1.0425(2) 0.47127(10) 1.06854(9) 0.0226(3) Uani d . 1 . . O C1 0.8539(3) 0.32184(16) 0.90651(14) 0.0268(4) Uani d . 1 . . C C2 0.9000(3) 0.42355(14) 0.91084(12) 0.0215(4) Uani d . 1 . . C C3 0.7817(3) 0.49665(14) 0.87385(13) 0.0224(4) Uani d . 1 . . C C4 0.6136(3) 0.46416(16) 0.83191(13) 0.0247(4) Uani d . 1 . . C C5 0.5673(4) 0.36347(18) 0.82348(14) 0.0299(5) Uani d . 1 . . C C6 0.6883(4) 0.29243(16) 0.86107(15) 0.0313(5) Uani d . 1 . . C C7 0.8835(3) 0.53413(14) 1.08739(12) 0.0197(4) Uani d . 1 . . C C8 0.8992(3) 0.63802(15) 1.08168(14) 0.0241(4) Uani d . 1 . . C C9 0.7417(3) 0.69705(15) 1.10415(15) 0.0258(4) Uani d . 1 . . C C10 0.5719(3) 0.65118(15) 1.13297(14) 0.0245(4) Uani d . 1 . . C C11 0.5549(3) 0.54799(15) 1.13981(13) 0.0236(4) Uani d . 1 . . C C12 0.7131(3) 0.48969(13) 1.11678(13) 0.0205(4) Uani d . 1 . . C H1 0.935(4) 0.2748(18) 0.9338(16) 0.025(6) Uiso d . 1 . . H H3 0.813(4) 0.5681(18) 0.8779(15) 0.029(6) Uiso d . 1 . . H H5 0.470(4) 0.3520(19) 0.7947(16) 0.028(7) Uiso d . 1 . . H H6 0.656(4) 0.225(2) 0.8561(17) 0.042(8) Uiso d . 1 . . H H8 0.999(4) 0.6661(17) 1.0625(15) 0.022(6) Uiso d . 1 . . H H9 0.755(4) 0.7601(19) 1.1020(15) 0.026(6) Uiso d . 1 . . H H11 0.447(4) 0.526(2) 1.1590(16) 0.031(7) 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 0.0228(2) 0.0310(2) 0.0517(3) 0.0073(2) 0.0069(2) -0.0040(2) Cl2 0.0280(3) 0.0203(2) 0.0434(3) -0.00461(19) 0.0014(2) 0.0053(2) S1 0.0146(2) 0.0221(2) 0.0292(2) 0.00210(18) 0.00254(19) 0.00104(18) N1 0.0225(9) 0.0479(11) 0.0235(8) 0.0066(9) 0.0022(7) 0.0036(8) O1 0.0269(9) 0.0703(12) 0.0342(9) 0.0097(8) -0.0102(7) -0.0110(8) O2 0.0254(8) 0.0397(9) 0.0563(11) 0.0052(7) 0.0003(8) 0.0170(8) O3 0.0212(7) 0.0282(7) 0.0370(8) -0.0039(6) 0.0043(6) 0.0035(6) O4 0.0205(7) 0.0319(7) 0.0411(9) 0.0096(6) 0.0034(6) 0.0020(7) O5 0.0174(7) 0.0238(6) 0.0265(7) 0.0040(6) -0.0013(5) 0.0013(5) C1 0.0290(11) 0.0219(9) 0.0294(10) 0.0013(9) 0.0031(9) -0.0013(8) C2 0.0187(9) 0.0227(8) 0.0229(9) 0.0005(8) 0.0042(8) -0.0023(7) C3 0.0209(10) 0.0232(8) 0.0230(9) 0.0006(8) 0.0045(8) 0.0013(7) C4 0.0197(9) 0.0331(10) 0.0214(9) 0.0035(9) 0.0039(8) 0.0010(8) C5 0.0252(11) 0.0410(12) 0.0234(10) -0.0080(10) 0.0025(9) -0.0083(9) C6 0.0348(12) 0.0252(9) 0.0338(11) -0.0040(9) 0.0039(10) -0.0063(9) C7 0.0157(8) 0.0221(8) 0.0213(9) 0.0019(8) -0.0003(7) -0.0023(7) C8 0.0165(9) 0.0236(9) 0.0323(11) -0.0053(8) 0.0009(8) 0.0002(8) C9 0.0233(10) 0.0182(8) 0.0359(11) -0.0022(8) -0.0004(8) -0.0039(8) C10 0.0169(9) 0.0263(9) 0.0303(10) 0.0047(7) 0.0004(8) -0.0042(8) C11 0.0167(9) 0.0265(9) 0.0276(10) -0.0035(8) 0.0024(8) -0.0006(8) C12 0.0198(9) 0.0188(8) 0.0230(9) -0.0022(7) -0.0024(8) 0.0008(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' 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 S1 O4 120.90(10) y O3 S1 O5 108.26(9) y O4 S1 O5 103.06(9) y O3 S1 C2 109.18(10) y O4 S1 C2 110.45(10) y O5 S1 C2 103.41(9) y O1 N1 O2 124.1(2) y O1 N1 C4 117.7(2) y O2 N1 C4 118.16(19) y C7 O5 S1 118.30(12) y C6 C1 C2 119.1(2) ? C6 C1 H1 121.2(16) ? C2 C1 H1 119.7(16) ? C3 C2 C1 122.1(2) ? C3 C2 S1 118.65(16) ? C1 C2 S1 119.22(16) ? C4 C3 C2 116.87(18) ? C4 C3 H3 121.1(15) ? C2 C3 H3 122.0(15) ? C3 C4 C5 122.4(2) ? C3 C4 N1 118.3(2) ? C5 C4 N1 119.3(2) ? C6 C5 C4 119.2(2) ? C6 C5 H5 125.8(18) ? C4 C5 H5 114.9(18) ? C5 C6 C1 120.2(2) ? C5 C6 H6 119.2(18) ? C1 C6 H6 120.6(18) ? C12 C7 C8 120.72(18) ? C12 C7 O5 117.84(17) ? C8 C7 O5 121.34(18) ? C9 C8 C7 119.4(2) ? C9 C8 H8 118.4(16) ? C7 C8 H8 122.1(16) ? C8 C9 C10 119.03(19) ? C8 C9 H9 118.3(18) ? C10 C9 H9 122.6(18) ? C11 C10 C9 122.17(19) ? C11 C10 Cl1 118.93(17) ? C9 C10 Cl1 118.89(16) ? C12 C11 C10 118.28(19) ? C12 C11 H11 125.5(18) ? C10 C11 H11 116.2(18) ? C11 C12 C7 120.37(18) ? C11 C12 Cl2 119.85(16) ? C7 C12 Cl2 119.77(15) ? 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 Cl1 C10 . 1.739(2) y Cl2 C12 . 1.722(2) y S1 O3 . 1.4229(17) y S1 O4 . 1.4240(16) y S1 O5 . 1.6006(18) y S1 C2 . 1.757(2) y N1 O1 . 1.219(3) y N1 O2 . 1.232(3) y N1 C4 . 1.467(3) y O5 C7 . 1.406(2) y C1 C6 . 1.384(3) ? C1 C2 . 1.394(3) ? C1 H1 . 0.94(3) ? C2 C3 . 1.386(3) ? C3 C4 . 1.385(3) ? C3 H3 . 0.98(2) ? C4 C5 . 1.385(3) ? C5 C6 . 1.381(4) ? C5 H5 . 0.81(3) ? C6 H6 . 0.93(3) ? C7 C12 . 1.385(3) ? C7 C8 . 1.392(3) ? C8 C9 . 1.381(3) ? C8 H8 . 0.84(3) ? C9 C10 . 1.387(3) ? C9 H9 . 0.85(2) ? C10 C11 . 1.384(3) ? C11 C12 . 1.381(3) ? C11 H11 . 0.85(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 C1 H1 O4 . 0.94(3) 2.63(3) 2.982(3) 102.8(17) y C3 H3 O2 . 0.98(2) 2.41(2) 2.708(3) 96.7(17) y C3 H3 O3 . 0.98(2) 2.60(3) 2.935(3) 100.2(17) y C5 H5 O1 . 0.81(3) 2.37(3) 2.716(3) 106(2) y C8 H8 O3 . 0.84(3) 2.65(2) 3.055(3) 111.3(18) y C6 H6 O5 4_457 0.93(3) 2.95(3) 3.805(3) 153(2) y C1 H1 O4 4_457 0.94(3) 2.83(2) 3.349(3) 116.1(19) y C9 H9 O2 4_567 0.85(2) 2.72(2) 3.294(3) 126(2) y C9 H9 O3 4_467 0.85(2) 2.56(3) 3.362(3) 158(2) y C11 H11 O1 2_565 0.85(3) 2.48(3) 3.301(3) 163(2) 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 S1 O5 C7 60.59(16) ? O4 S1 O5 C7 -170.24(14) ? C2 S1 O5 C7 -55.15(16) y C6 C1 C2 C3 2.4(3) ? C6 C1 C2 S1 -179.05(16) ? O3 S1 C2 C3 -22.82(18) ? O4 S1 C2 C3 -158.06(15) ? O5 S1 C2 C3 92.26(16) ? O3 S1 C2 C1 158.59(16) ? O4 S1 C2 C1 23.35(19) ? O5 S1 C2 C1 -86.33(17) ? C1 C2 C3 C4 0.0(3) ? S1 C2 C3 C4 -178.54(14) ? C2 C3 C4 C5 -2.5(3) ? C2 C3 C4 N1 177.46(17) ? O1 N1 C4 C3 177.05(19) ? O2 N1 C4 C3 -2.9(3) ? O1 N1 C4 C5 -3.0(3) ? O2 N1 C4 C5 177.12(19) ? C3 C4 C5 C6 2.6(3) ? N1 C4 C5 C6 -177.40(19) ? C4 C5 C6 C1 -0.1(3) ? C2 C1 C6 C5 -2.4(3) ? S1 O5 C7 C12 112.47(17) ? S1 O5 C7 C8 -71.1(2) ? C12 C7 C8 C9 -1.1(3) ? O5 C7 C8 C9 -177.47(18) ? C7 C8 C9 C10 0.8(3) ? C8 C9 C10 C11 -0.1(3) ? C8 C9 C10 Cl1 178.94(16) ? C9 C10 C11 C12 -0.1(3) ? Cl1 C10 C11 C12 -179.22(15) ? C10 C11 C12 C7 -0.2(3) ? C10 C11 C12 Cl2 178.58(16) ? C8 C7 C12 C11 0.9(3) ? O5 C7 C12 C11 177.33(17) ? C8 C7 C12 Cl2 -177.94(15) ? O5 C7 C12 Cl2 -1.5(2) ?