#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012065.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_2012065 loop_ _publ_author_name 'Ishida, Hiroyuki' 'Rahman, Bilkish' 'Kashino, Setsuo' _publ_section_title ; 2:1 Complexes of 2-chloro-4-nitrobenzoic acid and 2-chloro-5-nitrobenzoic acid with pyrazine ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 876 _journal_page_last 879 _journal_paper_doi 10.1107/S0108270101007016 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C4 H4 N2, 2C7 H4 Cl N O4' _chemical_formula_sum 'C18 H12 Cl2 N4 O8' _chemical_formula_weight 483.22 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 91.118(14) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 3.8280(5) _cell_length_b 12.7738(16) _cell_length_c 21.203(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 12.4 _cell_measurement_theta_min 11.1 _cell_volume 1036.6(2) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990) ; _computing_data_reduction 'TEXSAN for Windows (Molecular Structure Corporation, 1997-1999)' _computing_publication_material 'TEXSAN for Windows' _computing_structure_refinement 'TEXSAN for Windows' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 296 _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .031 _diffrn_reflns_av_sigmaI/netI .075 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 3559 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 1.60 _diffrn_standards_decay_% 1.57 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .368 _exptl_absorpt_correction_T_max .895 _exptl_absorpt_correction_T_min .862 _exptl_absorpt_correction_type '\y scans' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_meas ? _exptl_crystal_description prismatic _exptl_crystal_F_000 492 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .30 _refine_diff_density_max .39 _refine_diff_density_min -.49 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.38 _refine_ls_goodness_of_fit_ref 1.38 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 169 _refine_ls_number_reflns 2360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .077 _refine_ls_R_factor_gt .057 _refine_ls_shift/su_max .01 _refine_ls_shift/su_mean .0002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00003|Fo|^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all .074 _refine_ls_wR_factor_ref .063 _reflns_number_gt 1275 _reflns_number_total 2477 _reflns_threshold_expression I>2.0\s(I) _cod_data_source_file bk1601.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C18 H12 Cl2 N4 O8 ' _cod_database_code 2012065 _cod_database_fobs_code 2012065 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2+y,1/2-z ' -x, -y, -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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy Cl .38589(16) .65568(5) .18102(3) .0650(2) Uani d ? . 1.000 O1 .2745(5) .41390(14) .32294(8) .0704(6) Uani d ? . 1.000 O2 .4581(5) .57765(14) .31430(8) .0900(7) Uani d ? . 1.000 O3 .7819(6) .40493(17) .00424(9) .1141(9) Uani d ? . 1.000 O4 1.0445(5) .27749(14) .04790(8) .0950(8) Uani d ? . 1.000 N1 .8701(6) .35573(17) .05023(9) .0637(8) Uani d ? . 1.000 N2 .0822(5) .46729(16) .43978(9) .0572(7) Uani d ? . 1.000 C1 .5269(5) .45966(17) .22771(10) .0444(7) Uani d ? . 1.000 C2 .5288(5) .52768(15) .17643(10) .0450(7) Uani d ? . 1.000 C3 .6393(6) .49367(18) .11818(11) .0499(8) Uani d ? . 1.000 C4 .7520(5) .39189(17) .11241(10) .0475(7) Uani d ? . 1.000 C5 .7579(6) .32239(18) .16191(11) .0519(8) Uani d ? . 1.000 C6 .6388(6) .35739(18) .21922(11) .0505(8) Uani d ? . 1.000 C7 .4168(6) .49255(19) .29238(11) .0549(8) Uani d ? . 1.000 C8 .0792(8) .5669(2) .45539(13) .0721(10) Uani d ? . 1.000 C9 .0007(8) .5995(2) .51499(13) .0738(10) Uani d ? . 1.000 H1 .216(7) .434(2) .3588(13) .135(11) Uiso d ? . 1.000 H2 .629(5) .5377(13) .0853(8) .044(6) Uiso d ? . 1.000 H3 .833(5) .2524(16) .1561(9) .069(7) Uiso d ? . 1.000 H4 .633(4) .3070(14) .2545(8) .048(6) Uiso d ? . 1.000 H5 .134(6) .6151(18) .4241(10) .093(9) Uiso d ? . 1.000 H6 -.019(6) .6703(18) .5264(11) .094(9) Uiso d ? . 1.000 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 .0778(5) .0432(3) .0743(4) .0124(4) .0084(3) -.0066(3) O1 .0996(14) .0639(11) .0485(11) -.0191(10) .0234(10) -.0047(10) O2 .1423(18) .0617(12) .0675(13) -.0312(12) .0375(12) -.0219(10) O3 .171(2) .1232(17) .0492(12) .0631(15) .0201(13) .0047(12) O4 .1302(18) .0785(14) .0772(14) .0403(13) .0230(12) -.0206(11) N1 .0760(16) .0631(15) .0523(14) .0077(13) .0100(12) -.0124(12) N2 .0648(14) .0614(14) .0460(12) -.0082(11) .0142(10) .0028(11) C1 .0454(15) .0454(13) .0426(14) -.0058(11) .0073(11) -.0026(11) C2 .0450(14) .0378(12) .0522(15) -.0003(10) .0064(11) -.0075(11) C3 .0569(16) .0459(14) .0469(16) .0050(12) .0047(12) .0073(12) C4 .0505(15) .0505(14) .0417(13) .0034(12) .0078(11) -.0070(12) C5 .0613(17) .0402(14) .0544(16) .0047(12) .0024(13) -.0031(12) C6 .0597(16) .0456(15) .0462(15) -.0035(12) .0041(12) .0041(12) C7 .0598(17) .0575(16) .0478(16) -.0075(14) .0098(13) -.0046(13) C8 .107(2) .0611(19) .0490(18) -.0130(16) .0204(16) .0107(14) C9 .109(2) .0562(18) .0573(19) -.0067(18) .0215(17) .0013(16) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 ;International Tables for Crystallography (1992, Vol. C) ; H .000 .000 ;International Tables for Crystallography (1992, Vol. C) ; N .004 .003 ;International Tables for Crystallography (1992, Vol. C) ; O .008 .006 ;International Tables for Crystallography (1992, Vol. C) ; Cl .132 .159 ;International Tables for Crystallography (1992, Vol. C) ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 2 0 -1 2 -1 0 2 5 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 O1 H1 . . 109(2) no O3 N1 O4 . . 123.2(3) ? O3 N1 C4 . . 118.3(3) ? O4 N1 C4 . . 118.5(3) ? C8 N2 C9 . 3_566 115.9(3) ? C2 C1 C6 . . 118.7(2) ? C2 C1 C7 . . 123.0(2) ? C6 C1 C7 . . 118.3(2) ? Cl C2 C1 . . 122.71(19) ? Cl C2 C3 . . 116.8(2) ? C1 C2 C3 . . 120.5(2) ? C2 C3 C4 . . 118.6(3) ? C2 C3 H2 . . 119.2(14) no C4 C3 H2 . . 122.2(14) no N1 C4 C3 . . 118.5(2) ? N1 C4 C5 . . 118.6(2) ? C3 C4 C5 . . 122.9(3) ? C4 C5 C6 . . 117.5(3) ? C4 C5 H3 . . 120.7(15) no C6 C5 H3 . . 121.7(15) no C1 C6 C5 . . 121.8(3) ? C1 C6 H4 . . 120.3(12) no C5 C6 H4 . . 117.9(12) no O1 C7 O2 . . 123.8(3) ? O1 C7 C1 . . 111.2(2) ? O2 C7 C1 . . 125.0(3) ? N2 C8 C9 . . 122.0(3) ? N2 C8 H5 . . 117.2(17) no C9 C8 H5 . . 120.8(17) no N2 C9 C8 3_566 3_566 122.1(3) ? N2 C9 H6 3_566 3_566 114.4(18) no C8 C9 H6 . . 123.3(18) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl C2 . . 1.727(2) yes O1 C7 . . 1.319(3) yes O1 H1 . . .84(3) no O2 C7 . . 1.191(3) yes O3 N1 . . 1.203(3) yes O4 N1 . . 1.204(3) yes N1 C4 . . 1.476(3) yes N2 C8 . . 1.315(3) yes N2 C9 . 3_566 1.327(3) yes C1 C2 . . 1.392(3) yes C1 C6 . . 1.388(3) yes C1 C7 . . 1.502(3) yes C2 C3 . . 1.383(3) yes C3 C4 . . 1.376(3) yes C3 H2 . . .896(19) no C4 C5 . . 1.375(3) yes C5 C6 . . 1.380(3) yes C5 H3 . . .95(2) no C6 H4 . . .99(2) no C8 C9 . . 1.370(4) yes C8 H5 . . .93(3) no C9 H6 . . .94(3) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N2 2.686(3) . no O1 C6 3.327(3) 1_455 no O2 C5 3.345(3) 2_655 no O2 C8 3.352(4) . no O3 O3 2.955(6) 3_765 no O3 O3 3.252(5) 3_665 no O3 C3 3.294(4) 3_665 no O4 C8 3.053(4) 2_645 no O4 C9 3.173(4) 2_645 no O4 N1 3.314(4) 1_655 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 O1 H1 N2 . .84(3) 1.85(3) 2.686(3) 175(3) yes C3 H2 O3 3_665 .896(19) 2.55(2) 3.294(4) 140.9(18) yes C5 H3 O2 2_645 .95(2) 2.45(2) 3.345(3) 158(2) yes C8 H5 O4 2_655 .93(3) 2.48(3) 3.053(4) 120(2) yes 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 Cl C2 C1 C6 178.5(2) no Cl C2 C1 C7 -3.0(4) no Cl C2 C3 C4 -179.4(2) no O1 C7 C1 C2 149.1(3) no O1 C7 C1 C6 -32.4(4) no O2 C7 C1 C2 -32.5(4) no O2 C7 C1 C6 146.1(3) no O3 N1 C4 C3 -19.0(4) no O3 N1 C4 C5 160.7(3) no O4 N1 C4 C3 162.3(3) no O4 N1 C4 C5 -18.0(4) no N1 C4 C3 C2 -180.0(2) no N1 C4 C5 C6 -178.6(2) no C1 C2 C3 C4 -1.0(4) no C1 C6 C5 C4 -2.0(4) no C2 C1 C6 C5 1.4(4) no C2 C3 C4 C5 .3(4) no C3 C2 C1 C6 .2(4) no C3 C2 C1 C7 178.7(3) no C3 C4 C5 C6 1.2(4) no C5 C6 C1 C7 -177.2(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139058249