#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202497.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_2202497 loop_ _publ_author_name 'Nagarajan Vembu' 'Maruthai Nallu' 'Elinor C. Spencer' 'Judith A. K. Howard' _publ_section_title ; 2-Nitrophenyl 3-nitrobenzenesulfonate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1390 _journal_page_last o1392 _journal_paper_doi 10.1107/S1600536803018191 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C12 H8 N2 O7 S' _chemical_formula_moiety 'C12 H8 N2 O7 S' _chemical_formula_sum 'C12 H8 N2 O7 S' _chemical_formula_weight 324.26 _chemical_melting_point 359.0(10) _chemical_name_common 'o-Nitrophenyl m-nitrobenzenesulfonate' _chemical_name_systematic ; 2-Nitrophenyl 3-nitrobenzenesulfonate ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 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 19.9671(8) _cell_length_b 12.7083(5) _cell_length_c 5.1306(2) _cell_measurement_reflns_used 2719 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 26.681 _cell_measurement_theta_min 2.594 _cell_volume 1301.88(9) _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 120(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 9331 _diffrn_reflns_theta_full 27.11 _diffrn_reflns_theta_max 27.11 _diffrn_reflns_theta_min 1.90 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.183 _refine_diff_density_min -0.331 _refine_ls_abs_structure_details '(Flack, 1983), 1230 Friedel pairs' _refine_ls_abs_structure_Flack -0.10(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 223 _refine_ls_number_reflns 2832 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.962 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0338 _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^)+(0.0332P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.0699 _reflns_number_gt 2355 _reflns_number_total 2832 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6265.cif _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 '358-360' was changed to '359.0(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 '358-360' was changed to '359.0(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_database_code 2202497 _cod_database_fobs_code 2202497 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, 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 0.10099(11) 0.59508(17) 0.7938(5) 0.0226(5) Uani d . 1 . . C C2 0.09759(12) 0.68560(18) 0.6474(5) 0.0263(5) Uani d . 1 . . C H2 0.0626(12) 0.7325(19) 0.674(5) 0.032 Uiso d . 1 . . H C3 0.14536(12) 0.70336(18) 0.4570(5) 0.0290(6) Uani d . 1 . . C H3 0.1449(12) 0.7663(19) 0.347(5) 0.035 Uiso d . 1 . . H C4 0.19539(12) 0.62919(18) 0.4122(5) 0.0270(5) Uani d . 1 . . C H4 0.2278(12) 0.6363(19) 0.279(5) 0.032 Uiso d . 1 . . H C5 0.19640(10) 0.53812(16) 0.5619(4) 0.0219(5) Uani d . 1 . . C C6 0.14998(10) 0.51890(17) 0.7576(4) 0.0210(5) Uani d . 1 . . C H6 0.1521(11) 0.4514(17) 0.869(5) 0.025 Uiso d . 1 . . H C7 0.35510(10) 0.57182(16) 0.6233(4) 0.0206(5) Uani d . 1 . . C C8 0.34033(11) 0.66443(18) 0.7508(5) 0.0253(5) Uani d . 1 . . C H8 0.3064(12) 0.6656(17) 0.885(5) 0.030 Uiso d . 1 . . H C9 0.37541(11) 0.75507(18) 0.6868(5) 0.0275(5) Uani d . 1 . . C H9 0.3655(12) 0.818(2) 0.779(5) 0.033 Uiso d . 1 . . H C10 0.42276(10) 0.75352(17) 0.4901(6) 0.0258(5) Uani d . 1 . . C H10 0.4449(11) 0.8149(19) 0.441(5) 0.031 Uiso d . 1 . . H C11 0.43749(11) 0.66092(18) 0.3604(5) 0.0239(5) Uani d . 1 . . C H11 0.4698(12) 0.6597(17) 0.235(5) 0.029 Uiso d . 1 . . H C12 0.40411(10) 0.57001(16) 0.4328(4) 0.0204(5) Uani d . 1 . . C S1 0.25954(2) 0.44364(4) 0.50573(12) 0.02233(12) Uani d . 1 . . S O1 0.00775(8) 0.64556(11) 1.0301(4) 0.0348(4) Uani d . 1 . . O O2 0.05613(8) 0.49898(12) 1.1363(3) 0.0321(4) Uani d . 1 . . O O3 0.28079(8) 0.45294(12) 0.2416(3) 0.0293(4) Uani d . 1 . . O O4 0.24002(7) 0.34518(12) 0.6120(3) 0.0277(4) Uani d . 1 . . O O5 0.31924(7) 0.48061(11) 0.6923(3) 0.0225(3) Uani d . 1 . . O O6 0.42793(8) 0.39240(12) 0.4488(3) 0.0332(4) Uani d . 1 . . O O7 0.44083(8) 0.47339(13) 0.0786(3) 0.0340(4) Uani d . 1 . . O N1 0.05125(8) 0.57834(14) 1.0011(4) 0.0261(4) Uani d . 1 . . N N2 0.42532(8) 0.47095(15) 0.3104(4) 0.0247(4) Uani d . 1 . . N 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 0.0213(11) 0.0237(12) 0.0229(12) -0.0054(9) 0.0008(10) -0.0047(9) C2 0.0271(11) 0.0213(12) 0.0305(14) 0.0014(9) -0.0046(11) -0.0024(10) C3 0.0331(12) 0.0222(12) 0.0318(16) -0.0029(9) -0.0016(12) 0.0047(10) C4 0.0262(12) 0.0313(13) 0.0234(12) -0.0065(10) 0.0001(10) 0.0051(10) C5 0.0212(10) 0.0217(11) 0.0228(13) -0.0018(8) -0.0046(9) -0.0016(8) C6 0.0213(10) 0.0197(11) 0.0220(12) -0.0034(8) -0.0028(10) -0.0009(10) C7 0.0185(10) 0.0243(12) 0.0189(11) -0.0011(8) -0.0050(9) 0.0040(9) C8 0.0224(11) 0.0319(14) 0.0216(12) 0.0006(9) 0.0045(10) -0.0012(10) C9 0.0282(11) 0.0240(12) 0.0303(13) 0.0016(9) 0.0005(11) -0.0061(11) C10 0.0212(10) 0.0236(11) 0.0326(12) -0.0023(8) -0.0002(12) 0.0022(12) C11 0.0201(11) 0.0285(13) 0.0231(12) 0.0020(9) 0.0036(10) 0.0022(10) C12 0.0187(10) 0.0217(11) 0.0207(13) 0.0042(8) -0.0020(9) -0.0016(8) S1 0.0208(2) 0.0247(3) 0.0215(2) -0.0013(2) 0.0002(3) -0.0018(3) O1 0.0314(8) 0.0342(9) 0.0389(10) 0.0074(7) 0.0056(9) -0.0076(9) O2 0.0351(9) 0.0296(9) 0.0318(9) -0.0017(7) 0.0097(8) 0.0048(8) O3 0.0267(8) 0.0404(10) 0.0209(9) -0.0005(7) 0.0009(7) -0.0045(7) O4 0.0265(8) 0.0225(8) 0.0340(9) -0.0003(6) 0.0003(8) -0.0024(6) O5 0.0226(7) 0.0242(8) 0.0205(8) -0.0044(6) -0.0010(7) 0.0030(6) O6 0.0344(9) 0.0207(8) 0.0444(13) 0.0043(6) -0.0065(8) -0.0020(8) O7 0.0285(9) 0.0438(10) 0.0299(11) 0.0031(7) 0.0064(8) -0.0103(8) N1 0.0269(9) 0.0273(10) 0.0241(9) -0.0020(7) 0.0010(11) -0.0083(10) N2 0.0165(9) 0.0264(11) 0.0313(12) 0.0000(7) 0.0003(9) -0.0070(9) 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 C2 C1 C6 123.0(2) ? C2 C1 N1 118.9(2) ? C6 C1 N1 118.13(19) ? C1 C2 C3 119.2(2) ? C1 C2 H2 119.6(16) ? C3 C2 H2 121.2(16) ? C2 C3 C4 120.0(2) ? C2 C3 H3 122.3(15) ? C4 C3 H3 117.7(15) ? C5 C4 C3 118.9(2) ? C5 C4 H4 117.9(15) ? C3 C4 H4 123.1(15) ? C6 C5 C4 122.5(2) ? C6 C5 S1 118.39(16) ? C4 C5 S1 119.14(17) ? C5 C6 C1 116.4(2) ? C5 C6 H6 121.3(13) ? C1 C6 H6 122.3(13) ? C8 C7 C12 120.06(19) ? C8 C7 O5 118.36(19) ? C12 C7 O5 121.58(18) ? C7 C8 C9 119.2(2) ? C7 C8 H8 120.1(14) ? C9 C8 H8 120.7(14) ? C10 C9 C8 120.4(2) ? C10 C9 H9 121.2(15) ? C8 C9 H9 118.4(15) ? C9 C10 C11 120.5(2) ? C9 C10 H10 120.6(15) ? C11 C10 H10 118.9(15) ? C10 C11 C12 118.6(2) ? C10 C11 H11 120.3(15) ? C12 C11 H11 121.0(14) ? C7 C12 C11 121.07(19) ? C7 C12 N2 121.34(18) ? C11 C12 N2 117.49(19) ? O4 S1 O3 121.34(10) y O4 S1 O5 103.53(9) y O3 S1 O5 108.83(9) y O4 S1 C5 109.93(9) y O3 S1 C5 108.15(10) y O5 S1 C5 103.59(9) y C7 O5 S1 118.08(13) y O1 N1 O2 124.0(2) y O1 N1 C1 117.7(2) y O2 N1 C1 118.28(16) y O6 N2 O7 124.76(19) y O6 N2 C12 117.54(18) y O7 N2 C12 117.67(19) y 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 C2 . 1.376(3) ? C1 C6 . 1.389(3) ? C1 N1 . 1.471(3) y C2 C3 . 1.384(3) ? C2 H2 . 0.93(2) ? C3 C4 . 1.393(3) ? C3 H3 . 0.98(3) ? C4 C5 . 1.389(3) ? C4 H4 . 0.94(3) ? C5 C6 . 1.388(3) ? C5 S1 . 1.765(2) y C6 H6 . 1.03(2) ? C7 C8 . 1.378(3) ? C7 C12 . 1.383(3) ? C7 O5 . 1.408(2) y C8 C9 . 1.388(3) ? C8 H8 . 0.97(2) ? C9 C10 . 1.383(3) ? C9 H9 . 0.95(3) ? C10 C11 . 1.383(3) ? C10 H10 . 0.93(2) ? C11 C12 . 1.384(3) ? C11 H11 . 0.91(2) ? C12 N2 . 1.469(3) y S1 O4 . 1.4195(16) y S1 O3 . 1.4250(16) y S1 O5 . 1.5992(16) y O1 N1 . 1.227(2) y O2 N1 . 1.228(2) y O6 N2 . 1.226(2) y O7 N2 . 1.229(3) 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 . 0.93(2) 2.40(3) 2.708(3) 99.2(18) y C4 H4 O3 . 0.94(3) 2.57(2) 2.948(3) 104.5(17) y C6 H6 O2 . 1.03(2) 2.43(2) 2.711(3) 94.2(14) y C6 H6 O4 . 1.03(2) 2.58(2) 2.944(3) 100.4(16) y C11 H11 O7 . 0.91(2) 2.57(2) 2.788(3) 94.4(16) y C8 H8 O4 4 0.97(2) 2.72(2) 3.359(3) 123.8(17) y C9 H9 O4 4 0.95(3) 2.73(3) 3.374(3) 125.3(18) y C2 H2 O6 4 0.93(2) 2.48(2) 3.092(3) 123.5(18) y C3 H3 O6 4_554 0.98(3) 2.98(3) 3.836(3) 147.1(19) y C3 H3 O4 4_554 0.98(3) 2.78(3) 3.409(3) 122.5(18) y C9 H9 O2 4_554 0.95(3) 2.88(2) 3.398(3) 115.6(18) y C4 H4 O4 4_554 0.94(3) 2.86(2) 3.401(3) 117.3(18) y C10 H10 O2 4_554 0.93(2) 2.54(2) 3.236(3) 131.4(18) y C3 H3 O5 4_554 0.98(3) 2.93(2) 3.842(3) 156(2) y C10 H10 O1 3_564 0.93(2) 2.51(2) 3.177(3) 129.2(19) y C11 H11 O1 3_564 0.91(2) 2.79(2) 3.300(3) 116.2(17) y C11 H11 O6 2_664 0.91(2) 2.60(2) 3.484(3) 163.5(19) 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 -0.9(3) ? N1 C1 C2 C3 178.1(2) ? C1 C2 C3 C4 1.2(3) ? C2 C3 C4 C5 -0.2(3) ? C3 C4 C5 C6 -1.1(3) ? C3 C4 C5 S1 179.86(18) ? C4 C5 C6 C1 1.3(3) ? S1 C5 C6 C1 -179.63(16) ? C2 C1 C6 C5 -0.3(3) ? N1 C1 C6 C5 -179.35(18) ? C12 C7 C8 C9 -0.4(3) ? O5 C7 C8 C9 179.6(2) ? C7 C8 C9 C10 2.6(3) ? C8 C9 C10 C11 -2.2(4) ? C9 C10 C11 C12 -0.3(4) ? C8 C7 C12 C11 -2.2(3) ? O5 C7 C12 C11 177.80(19) ? C8 C7 C12 N2 174.3(2) ? O5 C7 C12 N2 -5.7(3) ? C10 C11 C12 C7 2.5(3) ? C10 C11 C12 N2 -174.1(2) ? C6 C5 S1 O4 19.79(19) ? C4 C5 S1 O4 -161.09(17) ? C6 C5 S1 O3 154.30(16) ? C4 C5 S1 O3 -26.6(2) ? C6 C5 S1 O5 -90.30(17) ? C4 C5 S1 O5 88.81(18) ? C8 C7 O5 S1 101.3(2) ? C12 C7 O5 S1 -78.7(2) ? O4 S1 O5 C7 173.34(15) ? O3 S1 O5 C7 43.00(16) ? C5 S1 O5 C7 -71.90(16) y C2 C1 N1 O1 1.6(3) ? C6 C1 N1 O1 -179.3(2) ? C2 C1 N1 O2 -177.6(2) ? C6 C1 N1 O2 1.5(3) ? C7 C12 N2 O6 -36.8(3) ? C11 C12 N2 O6 139.80(19) ? C7 C12 N2 O7 145.0(2) ? C11 C12 N2 O7 -38.3(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131531 2 PubChem 53531260