#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012066.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_2012066 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 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 105.17(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.293(4) _cell_length_b 7.276(2) _cell_length_c 13.818(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 10.0 _cell_volume 998.8(7) _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 'SAPI90 (Fan, 1990)' _diffrn_ambient_temperature 293 _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 .039 _diffrn_reflns_av_sigmaI/netI .106 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2887 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 1.52 _diffrn_standards_decay_% 1.57 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .382 _exptl_absorpt_correction_T_max .926 _exptl_absorpt_correction_T_min .810 _exptl_absorpt_correction_type '\y scans' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.606 _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 .20 _refine_diff_density_max .44 _refine_diff_density_min -.61 _refine_ls_extinction_coef 2.48(9)\\times10^-6^ _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_all 1.33 _refine_ls_goodness_of_fit_ref 1.33 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 170 _refine_ls_number_reflns 2292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .072 _refine_ls_R_factor_gt .051 _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) + 0.00001|Fo|^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all .070 _refine_ls_wR_factor_ref .061 _reflns_number_gt 1268 _reflns_number_total 2293 _reflns_threshold_expression I>2.0\s(I) _cod_data_source_file bk1601.cif _cod_data_source_block II _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_cell_volume 998.9(6) _cod_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum 'C18 H12 Cl2 N4 O8 ' _cod_database_code 2012066 _cod_database_fobs_code 2012066 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +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 .02826(7) .10612(10) .27895(5) .0535(2) Uani d ? . 1.000 O1 .12332(17) .3384(3) .00595(13) .0590(7) Uani d ? . 1.000 O2 .20442(16) .2408(3) .16189(13) .0633(6) Uani d ? . 1.000 O3 -.45413(17) .0651(3) -.14017(13) .0761(7) Uani d ? . 1.000 O4 -.30575(18) .2081(3) -.19589(13) .0734(7) Uani d ? . 1.000 N1 -.3433(2) .1338(3) -.12914(15) .0523(8) Uani d ? . 1.000 N2 .37543(19) .4335(3) .00226(16) .0503(7) Uani d ? . 1.000 C1 -.0288(2) .1914(3) .07882(16) .0318(7) Uani d ? . 1.000 C2 -.0734(2) .1155(3) .15764(16) .0344(7) Uani d ? . 1.000 C3 -.2028(3) .0470(4) .14345(19) .0438(9) Uani d ? . 1.000 C4 -.2909(2) .0510(4) .04937(18) .0429(8) Uani d ? . 1.000 C5 -.2489(2) .1275(3) -.02785(16) .0368(7) Uani d ? . 1.000 C6 -.1211(2) .1962(3) -.01528(17) .0359(8) Uani d ? . 1.000 C7 .1126(2) .2608(4) .08890(18) .0388(8) Uani d ? . 1.000 C8 .4022(3) .4841(4) -.0834(2) .0559(10) Uani d ? . 1.000 C9 .4738(3) .4488(4) .0859(2) .0522(9) Uani d ? . 1.000 H1 .218(3) .372(4) .010(2) .113(11) Uiso d ? . 1.000 H2 -.228(2) -.001(3) .2005(14) .046(7) Uiso d ? . 1.000 H3 -.3819(18) .004(3) .0371(14) .039(7) Uiso d ? . 1.000 H4 -.0982(17) .250(3) -.0713(13) .018(5) Uiso d ? . 1.000 H5 .335(2) .469(3) -.1431(15) .046(7) Uiso d ? . 1.000 H6 .4542(19) .414(3) .1505(14) .040(6) 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 .0531(4) .0694(5) .0341(3) -.0077(4) .0045(3) .0039(4) O1 .0318(11) .0914(17) .0534(12) -.0155(11) .0104(9) .0172(11) O2 .0355(10) .1071(18) .0424(10) -.0106(11) .0018(8) -.0016(12) O3 .0356(11) .125(2) .0604(13) -.0259(13) -.0003(9) .0014(14) O4 .0600(14) .1105(19) .0428(11) -.0215(13) .0013(10) .0148(12) N1 .0419(14) .0687(19) .0431(13) -.0010(13) .0053(11) -.0028(13) N2 .0343(12) .0613(18) .0567(14) -.0073(12) .0146(11) .0052(14) C1 .0324(13) .0323(15) .0328(13) .0006(12) .0122(10) -.0059(12) C2 .0373(14) .0333(16) .0311(12) .0012(13) .0062(10) -.0058(13) C3 .0437(16) .048(2) .0432(15) -.0046(14) .0187(13) .0034(14) C4 .0320(15) .052(2) .0453(15) -.0062(14) .0118(12) .0026(14) C5 .0321(13) .0408(17) .0359(13) .0017(13) .0062(10) -.0001(13) C6 .0383(15) .0368(17) .0346(14) -.0016(13) .0130(12) -.0008(13) C7 .0376(15) .0395(17) .0420(15) -.0059(13) .0151(12) -.0094(14) C8 .0411(18) .077(3) .0458(17) -.0088(16) .0041(14) .0007(17) C9 .0420(16) .069(2) .0469(17) -.0024(16) .0139(13) .0089(17) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl .132 .159 ;International Tables for Crystallography (1992, Vol. C) ; O .008 .006 ;International Tables for Crystallography (1992, Vol. C) ; N .004 .003 ;International Tables for Crystallography (1992, Vol. C) ; C .002 .002 ;International Tables for Crystallography (1992, Vol. C) ; H .000 .000 ;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 2 -1 2 1 1 2 0 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 . . 111.3(18) no O3 N1 O4 . . 124.1(3) ? O3 N1 C5 . . 117.8(3) ? O4 N1 C5 . . 118.1(2) ? C8 N2 C9 . . 117.5(3) ? C2 C1 C6 . . 116.9(3) ? C2 C1 C7 . . 124.3(2) ? C6 C1 C7 . . 118.8(2) ? Cl C2 C1 . . 122.0(2) ? Cl C2 C3 . . 116.0(2) ? C1 C2 C3 . . 122.0(3) ? C2 C3 C4 . . 119.8(3) ? C2 C3 H2 . . 118.3(15) no C4 C3 H2 . . 121.9(15) no C3 C4 C5 . . 118.6(3) ? C3 C4 H3 . . 121.6(13) no C5 C4 H3 . . 119.7(13) no N1 C5 C4 . . 119.1(3) ? N1 C5 C6 . . 118.5(3) ? C4 C5 C6 . . 122.4(3) ? C1 C6 C5 . . 120.3(3) ? C1 C6 H4 . . 121.1(12) no C5 C6 H4 . . 118.6(12) no O1 C7 O2 . . 124.2(3) ? O1 C7 C1 . . 111.3(2) ? O2 C7 C1 . . 124.5(3) ? N2 C8 C9 . 3_665 121.9(3) ? N2 C8 H5 . . 118.5(16) no C9 C8 H5 3_665 3_665 119.5(16) no N2 C9 C8 . 3_665 120.6(3) ? N2 C9 H6 . . 118.1(13) no C8 C9 H6 3_665 3_665 121.3(13) 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 . . 1.730(3) yes O1 C7 . . 1.308(3) yes O1 H1 . . 1.00(3) no O2 C7 . . 1.197(3) yes O3 N1 . . 1.218(3) yes O4 N1 . . 1.216(3) yes N1 C5 . . 1.481(3) yes N2 C8 . . 1.335(3) yes N2 C9 . . 1.327(4) yes C1 C2 . . 1.401(3) yes C1 C6 . . 1.396(3) yes C1 C7 . . 1.512(3) yes C2 C3 . . 1.387(4) yes C3 C4 . . 1.377(4) yes C3 H2 . . .96(2) no C4 C5 . . 1.370(4) yes C4 H3 . . .97(2) no C5 C6 . . 1.375(3) yes C6 H4 . . .951(19) no C8 C9 . 3_665 1.376(4) yes C8 H5 . . .93(2) no C9 H6 . . 1.00(2) 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 2.699(3) . no O1 C6 3.389(4) 3_565 no O2 N1 3.165(4) 3 no O2 C5 3.357(4) 3 no O3 C4 3.301(4) 3_455 no O4 C3 3.234(4) 4_554 no O4 C8 3.371(4) 2_544 no C5 C7 3.359(4) 3 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 . 1.00(3) 1.71(3) 2.699(3) 173(3) yes C3 H2 O2 2_545 .96(2) 2.64(2) 3.496(4) 149.3(19) yes C4 H3 O3 3_455 .97(2) 2.53(2) 3.301(4) 136.8(17) 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 -178.2(2) no Cl C2 C1 C7 4.1(4) no Cl C2 C3 C4 179.3(3) no O1 C7 C1 C2 -174.6(3) no O1 C7 C1 C6 7.7(4) no O2 C7 C1 C2 8.1(5) no O2 C7 C1 C6 -169.5(3) no O3 N1 C5 C4 -2.1(4) no O3 N1 C5 C6 176.8(3) no O4 N1 C5 C4 177.4(3) no O4 N1 C5 C6 -3.7(4) no N1 C5 C4 C3 -179.5(3) no N1 C5 C6 C1 -179.5(3) no C1 C2 C3 C4 .7(5) no C1 C6 C5 C4 -.6(5) no C2 C1 C6 C5 -.4(4) no C2 C3 C4 C5 -1.6(5) no C3 C2 C1 C6 .4(4) no C3 C2 C1 C7 -177.3(3) no C3 C4 C5 C6 1.6(5) no C5 C6 C1 C7 177.4(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139058250