#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/24/2202496.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_2202496 loop_ _publ_author_name 'Vembu, Nagarajan' 'Nallu, Maruthai' 'Spencer, Elinor C.' 'Howard, Judith A. K.' _publ_section_title ; 2,4-Dinitrophenyl 3-nitrobenzenesulfonate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1387 _journal_page_last o1389 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C12 H7 N3 O9 S' _chemical_formula_moiety 'C12 H7 N3 O9 S' _chemical_formula_sum 'C12 H7 N3 O9 S' _chemical_formula_weight 369.27 _chemical_melting_point 378.0(10) _chemical_name_common '2,4-dinitrophenyl m-nitrobenzenesulfonate' _chemical_name_systematic ; 2,4-Dinitrophenyl 3-nitrobenzenesulfonate ; _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 27.730(2) _cell_length_b 4.7374(3) _cell_length_c 10.7800(8) _cell_measurement_reflns_used 3073 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.07 _cell_measurement_theta_min 2.39 _cell_volume 1416.15(17) _computing_cell_refinement SMART-NT _computing_data_collection 'SMART-NT (Bruker, 1998)' _computing_data_reduction 'SAINT-NT (Bruker, 1998)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.033 _diffrn_reflns_av_sigmaI/netI 0.043 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8989 _diffrn_reflns_theta_full 27.11 _diffrn_reflns_theta_max 27.11 _diffrn_reflns_theta_min 2.94 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.290 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.732 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.34 _refine_diff_density_min -0.33 _refine_ls_abs_structure_details '(Flack, 1983); 1310 Friedel pairs' _refine_ls_abs_structure_Flack -0.05(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 247 _refine_ls_number_reflns 2952 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.967 _refine_ls_R_factor_all 0.036 _refine_ls_R_factor_gt 0.030 _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^)+(0.0274P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.058 _refine_ls_wR_factor_ref 0.059 _reflns_number_gt 2619 _reflns_number_total 2952 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6264.cif _[local]_cod_data_source_block I _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 '377-379' was changed to '378.0(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 '377-379' was changed to '378.0(10)' - 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 1416.16(17) _cod_database_code 2202496 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.63940(7) 0.8435(4) 0.11796(18) 0.0177(4) Uani d . 1 . . C C2 0.67868(8) 1.0065(4) 0.0840(2) 0.0219(5) Uani d . 1 . . C H2 0.6760(7) 1.124(5) 0.013(2) 0.026 Uiso d . 1 . . H C3 0.71927(8) 1.0039(5) 0.1583(2) 0.0242(5) Uani d . 1 . . C H3 0.7474(9) 1.113(4) 0.134(2) 0.029 Uiso d . 1 . . H C4 0.72028(7) 0.8437(4) 0.2661(2) 0.0194(4) Uani d . 1 . . C H4 0.7483(9) 0.842(4) 0.315(2) 0.023 Uiso d . 1 . . H C5 0.67987(7) 0.6855(4) 0.29759(19) 0.0146(4) Uani d . 1 . . C C6 0.63895(8) 0.6804(4) 0.22407(19) 0.0175(4) Uani d . 1 . . C H6 0.6131(8) 0.564(4) 0.250(2) 0.021 Uiso d . 1 . . H C7 0.61813(7) 0.6853(4) 0.58859(19) 0.0154(4) Uani d . 1 . . C C8 0.58006(8) 0.8235(4) 0.5321(2) 0.0179(4) Uani d . 1 . . C H8 0.5841(7) 0.913(4) 0.469(2) 0.021 Uiso d . 1 . . H C9 0.53528(8) 0.8283(4) 0.5895(2) 0.0188(5) Uani d . 1 . . C H9 0.5118(8) 0.909(4) 0.551(2) 0.023 Uiso d . 1 . . H C10 0.52982(7) 0.6906(4) 0.70080(19) 0.0166(4) Uani d . 1 . . C C11 0.56676(7) 0.5508(4) 0.7602(2) 0.0181(4) Uani d . 1 . . C H11 0.5631(8) 0.453(4) 0.831(2) 0.022 Uiso d . 1 . . H C12 0.61079(7) 0.5526(4) 0.70134(18) 0.0155(4) Uani d . 1 . . C S1 0.680852(17) 0.47848(9) 0.43241(5) 0.01655(11) Uani d . 1 . . S N1 0.59615(6) 0.8425(4) 0.03865(17) 0.0234(4) Uani d . 1 . . N N2 0.65165(6) 0.4156(4) 0.76543(17) 0.0200(4) Uani d . 1 . . N N3 0.48240(6) 0.6976(4) 0.76390(18) 0.0238(4) Uani d . 1 . . N O1 0.59276(5) 1.0242(3) -0.04173(15) 0.0303(4) Uani d . 1 . . O O2 0.56581(5) 0.6588(4) 0.05693(15) 0.0279(4) Uani d . 1 . . O O3 0.72932(5) 0.4132(3) 0.46165(14) 0.0247(4) Uani d . 1 . . O O4 0.64466(5) 0.2683(3) 0.42225(15) 0.0211(3) Uani d . 1 . . O O5 0.66457(5) 0.6961(3) 0.54078(13) 0.0179(3) Uani d . 1 . . O O6 0.67106(6) 0.2177(3) 0.71487(15) 0.0339(4) Uani d . 1 . . O O7 0.66216(6) 0.5114(3) 0.86734(14) 0.0299(4) Uani d . 1 . . O O8 0.45300(5) 0.8714(3) 0.72981(15) 0.0321(4) Uani d . 1 . . O O9 0.47545(6) 0.5267(4) 0.84620(17) 0.0437(5) Uani d . 1 . . O 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 0.0152(11) 0.0196(11) 0.0182(11) 0.0031(9) -0.0017(8) -0.0035(8) C2 0.0258(12) 0.0228(11) 0.0170(11) 0.0027(10) 0.0024(9) 0.0049(9) C3 0.0216(12) 0.0256(12) 0.0255(12) -0.0049(10) 0.0046(9) 0.0056(10) C4 0.0159(11) 0.0235(11) 0.0189(11) -0.0006(9) 0.0020(9) 0.0021(10) C5 0.0151(10) 0.0144(10) 0.0142(10) 0.0048(9) 0.0024(8) 0.0031(8) C6 0.0178(10) 0.0152(10) 0.0194(12) 0.0017(9) 0.0024(9) -0.0006(8) C7 0.0152(10) 0.0149(10) 0.0160(11) -0.0028(8) 0.0035(8) -0.0025(8) C8 0.0221(11) 0.0182(11) 0.0133(11) -0.0030(9) -0.0007(9) 0.0055(8) C9 0.0163(11) 0.0203(11) 0.0197(11) 0.0007(9) -0.0049(8) 0.0009(9) C10 0.0125(10) 0.0209(11) 0.0164(11) -0.0009(8) -0.0004(8) -0.0015(8) C11 0.0194(11) 0.0215(11) 0.0134(11) -0.0022(9) 0.0007(9) 0.0019(9) C12 0.0146(10) 0.0169(10) 0.0150(11) 0.0014(8) -0.0021(8) -0.0007(8) S1 0.0162(2) 0.0174(2) 0.0160(2) 0.0025(2) 0.0025(2) 0.0041(2) N1 0.0247(10) 0.0262(10) 0.0194(10) 0.0058(9) -0.0012(8) -0.0043(8) N2 0.0179(9) 0.0263(9) 0.0159(9) -0.0004(8) 0.0014(8) 0.0062(8) N3 0.0162(9) 0.0344(11) 0.0207(10) -0.0018(8) 0.0008(8) 0.0011(9) O1 0.0361(9) 0.0296(8) 0.0253(10) 0.0083(7) -0.0088(7) 0.0082(7) O2 0.0244(8) 0.0335(9) 0.0259(9) -0.0030(8) -0.0049(7) -0.0019(7) O3 0.0200(8) 0.0312(8) 0.0230(9) 0.0079(6) 0.0020(6) 0.0093(6) O4 0.0256(8) 0.0152(6) 0.0227(8) -0.0018(6) 0.0045(7) 0.0025(6) O5 0.0136(7) 0.0221(8) 0.0181(8) -0.0027(6) 0.0023(6) 0.0015(6) O6 0.0330(9) 0.0402(10) 0.0286(10) 0.0214(8) -0.0008(8) -0.0027(8) O7 0.0291(8) 0.0388(9) 0.0218(9) 0.0056(7) -0.0101(7) 0.0005(7) O8 0.0187(8) 0.0411(9) 0.0364(11) 0.0112(7) 0.0041(7) 0.0068(8) O9 0.0219(9) 0.0711(13) 0.0382(12) 0.0029(9) 0.0073(8) 0.0315(10) 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 C1 C6 . 1.380(3) ? C1 C2 . 1.385(3) ? C1 N1 . 1.473(3) y C2 C3 . 1.382(3) ? C2 H2 . 0.95(2) ? C3 C4 . 1.388(3) ? C3 H3 . 0.97(2) ? C4 C5 . 1.390(3) ? C4 H4 . 0.94(2) ? C5 C6 . 1.384(3) ? C5 S1 . 1.753(2) y C6 H6 . 0.95(2) ? C7 C8 . 1.383(3) ? C7 C12 . 1.384(3) ? C7 O5 . 1.388(2) ? C8 C9 . 1.387(3) ? C8 H8 . 0.81(2) ? C9 C10 . 1.374(3) ? C9 H9 . 0.86(2) ? C10 C11 . 1.378(3) ? C10 N3 . 1.481(2) y C11 C12 . 1.376(3) ? C11 H11 . 0.90(2) ? C12 N2 . 1.477(2) y S1 O3 . 1.4147(15) y S1 O4 . 1.4182(13) y S1 O5 . 1.6222(15) y N1 O1 . 1.225(2) y N1 O2 . 1.227(2) y N2 O6 . 1.211(2) y N2 O7 . 1.224(2) y N3 O8 . 1.216(2) y N3 O9 . 1.216(2) y 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 C6 C1 C2 122.58(19) ? C6 C1 N1 118.16(18) ? C2 C1 N1 119.27(18) ? C3 C2 C1 118.8(2) ? C3 C2 H2 122.4(13) ? C1 C2 H2 118.6(13) ? C2 C3 C4 120.5(2) ? C2 C3 H3 119.5(14) ? C4 C3 H3 120.0(14) ? C3 C4 C5 118.9(2) ? C3 C4 H4 119.5(14) ? C5 C4 H4 121.6(14) ? C6 C5 C4 122.03(19) ? C6 C5 S1 118.52(16) ? C4 C5 S1 119.43(16) ? C1 C6 C5 117.21(19) ? C1 C6 H6 125.3(14) ? C5 C6 H6 117.5(14) ? C8 C7 C12 119.30(18) ? C8 C7 O5 121.82(18) ? C12 C7 O5 118.65(18) ? C7 C8 C9 119.66(19) ? C7 C8 H8 120.9(15) ? C9 C8 H8 119.2(15) ? C10 C9 C8 118.7(2) ? C10 C9 H9 123.4(16) ? C8 C9 H9 117.8(16) ? C9 C10 C11 123.52(18) ? C9 C10 N3 119.23(17) ? C11 C10 N3 117.22(18) ? C12 C11 C10 116.26(19) ? C12 C11 H11 119.6(15) ? C10 C11 H11 124.0(15) ? C11 C12 C7 122.58(18) ? C11 C12 N2 117.53(17) ? C7 C12 N2 119.85(17) ? O3 S1 O4 122.42(8) y O3 S1 O5 104.06(8) y O4 S1 O5 107.75(8) y O3 S1 C5 108.77(9) y O4 S1 C5 108.53(10) y O5 S1 C5 103.71(8) y O1 N1 O2 124.03(18) y O1 N1 C1 118.10(18) y O2 N1 C1 117.88(17) y O6 N2 O7 125.83(17) y O6 N2 C12 118.07(17) y O7 N2 C12 116.08(17) y O8 N3 O9 124.40(18) y O8 N3 C10 118.16(17) y O9 N3 C10 117.44(17) y C7 O5 S1 120.15(12) y 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 . 0.95(2) 2.43(2) 2.742(3) 99.0(15) y C4 H4 O3 . 0.94(2) 2.63(2) 2.944(3) 100.4(15) y C6 H6 O2 . 0.95(2) 2.50(2) 2.715(3) 92.7(15) y C6 H6 O4 . 0.95(2) 2.49(2) 2.898(2) 106.4(16) y C9 H9 O8 . 0.86(2) 2.53(2) 2.745(3) 94.9(18) y C11 H11 O9 . 0.90(2) 2.46(2) 2.699(3) 95.3(16) y C2 H2 O7 1_564 0.95(2) 2.45(2) 3.374(3) 166.2(19) y C3 H3 O3 4_664 0.97(2) 2.43(2) 3.208(3) 137.0(18) y C3 H3 O6 4_664 0.97(2) 2.47(2) 3.263(3) 138.2(18) y C4 H4 O7 4_654 0.94(2) 2.99(2) 3.781(3) 142.9(17) y C6 H6 N3 2_664 0.95(2) 2.93(2) 3.836(3) 161.2(18) y C6 H6 O8 2_664 0.95(2) 2.77(2) 3.652(3) 155.7(19) y C6 H6 O9 2_664 0.95(2) 2.70(2) 3.572(3) 153.6(17) y C8 H8 O4 1_565 0.81(2) 2.43(2) 3.008(2) 129.2(19) y C8 H8 O8 2_674 0.81(2) 2.96(2) 3.681(3) 150.0(18) y C9 H9 O2 2_675 0.86(2) 2.97(2) 3.726(3) 147(2) y C11 H11 O1 1_546 0.90(2) 2.58(2) 3.362(3) 145.1(18) y C11 H11 O2 1_556 0.90(2) 2.62(2) 3.240(3) 126.4(17) 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 C6 C1 C2 C3 0.7(3) ? N1 C1 C2 C3 -179.36(19) ? C1 C2 C3 C4 -1.0(3) ? C2 C3 C4 C5 0.3(3) ? C3 C4 C5 C6 0.7(3) ? C3 C4 C5 S1 179.18(16) ? C2 C1 C6 C5 0.2(3) ? N1 C1 C6 C5 -179.69(17) ? C4 C5 C6 C1 -1.0(3) ? S1 C5 C6 C1 -179.42(15) ? C12 C7 C8 C9 0.3(3) ? O5 C7 C8 C9 -174.04(19) ? C7 C8 C9 C10 -1.0(3) ? C8 C9 C10 C11 1.1(3) ? C8 C9 C10 N3 179.11(18) ? C9 C10 C11 C12 -0.5(3) ? N3 C10 C11 C12 -178.51(17) ? C10 C11 C12 C7 -0.3(3) ? C10 C11 C12 N2 177.28(17) ? C8 C7 C12 C11 0.3(3) ? O5 C7 C12 C11 174.87(18) ? C8 C7 C12 N2 -177.16(17) ? O5 C7 C12 N2 -2.6(3) ? C6 C5 S1 O3 154.18(15) ? C4 C5 S1 O3 -24.31(19) ? C6 C5 S1 O4 18.87(18) ? C4 C5 S1 O4 -159.63(15) ? C6 C5 S1 O5 -95.51(16) ? C4 C5 S1 O5 86.00(17) ? C6 C1 N1 O1 166.58(18) ? C2 C1 N1 O1 -13.3(3) ? C6 C1 N1 O2 -13.7(3) ? C2 C1 N1 O2 166.39(18) ? C11 C12 N2 O6 119.0(2) ? C7 C12 N2 O6 -63.4(2) ? C11 C12 N2 O7 -59.6(2) ? C7 C12 N2 O7 118.1(2) ? C9 C10 N3 O8 -15.3(3) ? C11 C10 N3 O8 162.79(19) ? C9 C10 N3 O9 164.2(2) ? C11 C10 N3 O9 -17.7(3) ? C8 C7 O5 S1 -84.7(2) ? C12 C7 O5 S1 100.94(19) ? O3 S1 O5 C7 -142.85(14) ? O4 S1 O5 C7 -11.52(16) ? C5 S1 O5 C7 103.41(15) y _cod_database_fobs_code 2202496