#------------------------------------------------------------------------------ #$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/18/2011867.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_2011867 loop_ _publ_author_name ' Ishida, Hiroyuki ' ' Kashino, Setsuo ' _publ_section_title ; 1:2 Complexes of chloranilic acid with pyrazole and imidazole, and the acetonitrile solvate of a 1:1 complex with imidazole ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 476 _journal_page_last 479 _journal_paper_doi 10.1107/S0108270101000944 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C3 H5 N2 1+, C6 H Cl2 O4 1-, C2 H3 N' _chemical_formula_sum 'C11 H9 Cl2 N3 O4' _chemical_formula_weight 318.12 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 95.86(2) _cell_angle_beta 99.82(2) _cell_angle_gamma 111.156(16) _cell_formula_units_Z 2 _cell_length_a 9.3895(19) _cell_length_b 9.628(2) _cell_length_c 8.214(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 297 _cell_measurement_theta_max 12.3 _cell_measurement_theta_min 10.7 _cell_volume 671.5(3) _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., 1994)' _diffrn_ambient_temperature 297 _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 .02310 _diffrn_reflns_av_sigmaI/netI .059 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3283 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.31 _diffrn_standards_decay_% none _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .499 _exptl_absorpt_correction_T_max .88 _exptl_absorpt_correction_T_min .84 _exptl_absorpt_correction_type '\y scans' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour 'dark brown' _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_meas ? _exptl_crystal_description prismatic _exptl_crystal_F_000 324 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .25 _refine_diff_density_max .41 _refine_diff_density_min -.45 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.37 _refine_ls_goodness_of_fit_ref 1.37 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 217 _refine_ls_number_reflns 3093 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .062 _refine_ls_R_factor_gt .052 _refine_ls_shift/su_max .01 _refine_ls_shift/su_mean .0003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00006|Fo|^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all .069 _refine_ls_wR_factor_ref .063 _reflns_number_gt 2048 _reflns_number_total 3093 _reflns_threshold_expression I>2.00\s(I) _cod_data_source_file de1164.cif _cod_data_source_block III _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 671.4(3) _cod_original_sg_symbol_H-M 'P -1 ' _cod_original_formula_sum 'C11 H9 Cl2 N3 O4 ' _cod_database_code 2011867 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -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 Cl1 .09437(6) -.23493(5) -.21826(6) .04240(15) Uani d ? . 1.000 Cl2 .02691(6) .39836(5) -.16726(7) .04850(16) Uani d ? . 1.000 O1 .27177(14) .04715(14) .03616(16) .0416(4) Uani d ? . 1.000 O2 -.14564(14) -.15415(13) -.44194(16) .0417(4) Uani d ? . 1.000 O3 -.18037(15) .11123(14) -.40303(16) .0419(4) Uani d ? . 1.000 O4 .25179(16) .31178(15) .05331(17) .0436(4) Uani d ? . 1.000 N1 .4168(2) -.1310(2) .1539(2) .0443(5) Uani d ? . 1.000 N2 .6001(2) -.1492(2) .3339(2) .0471(6) Uani d ? . 1.000 N3 .5128(3) .3372(3) .3019(3) .0835(8) Uani d ? . 1.000 C1 .1657(2) .05204(19) -.0759(2) .0294(5) Uani d ? . 1.000 C2 .0658(2) -.06625(18) -.2055(2) .0297(5) Uani d ? . 1.000 C3 -.0532(2) -.05324(19) -.3239(2) .0300(5) Uani d ? . 1.000 C4 -.0720(2) .10064(19) -.3072(2) .0295(5) Uani d ? . 1.000 C5 .0403(2) .22383(18) -.1788(2) .0318(5) Uani d ? . 1.000 C6 .1497(2) .20174(19) -.0685(2) .0309(5) Uani d ? . 1.000 C7 .5365(3) -.0563(3) .2829(3) .0477(7) Uani d ? . 1.000 C8 .4059(3) -.2758(3) .1236(3) .0524(7) Uani d ? . 1.000 C9 .5196(3) -.2880(3) .2345(3) .0532(7) Uani d ? . 1.000 C10 .6242(3) .3943(2) .3986(3) .0513(7) Uani d ? . 1.000 C11 .7691(4) .4704(4) .5226(4) .0678(9) Uani d ? . 1.000 H1 .316(3) .278(3) .109(3) .086(8) Uiso d ? . 1.000 H2 .361(3) -.077(3) .104(3) .089(8) Uiso d ? . 1.000 H3 .571(2) .052(2) .332(3) .070(7) Uiso d ? . 1.000 H4 .691(3) -.121(3) .421(3) .087(8) Uiso d ? . 1.000 H5 .546(3) -.377(3) .252(3) .081(8) Uiso d ? . 1.000 H6 .334(3) -.347(3) .045(3) .083(8) Uiso d ? . 1.000 H7 .804(4) .403(4) .559(5) .178(13) Uiso d ? . 1.000 H8 .749(3) .500(3) .609(4) .105(11) Uiso d ? . 1.000 H9 .826(5) .551(4) .480(5) .194(14) 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 Cl1 .0469(3) .0315(3) .0473(3) .0216(2) -.0044(2) .0018(2) Cl2 .0606(4) .0344(3) .0501(3) .0284(3) -.0075(3) .0013(2) O1 .0375(8) .0413(8) .0409(8) .0205(7) -.0127(6) .0021(6) O2 .0428(8) .0351(7) .0382(8) .0167(7) -.0115(6) -.0043(6) O3 .0414(8) .0448(8) .0389(8) .0248(7) -.0087(6) .0034(6) O4 .0416(8) .0358(8) .0422(9) .0157(7) -.0133(7) -.0062(6) N1 .0370(10) .0551(11) .0469(11) .0263(9) .0020(8) .0157(9) N2 .0333(10) .0632(12) .0411(11) .0175(10) -.0021(8) .0150(10) N3 .0683(15) .0765(15) .0774(16) .0204(13) -.0291(12) -.0050(13) C1 .0264(9) .0330(10) .0302(10) .0145(8) .0027(8) .0067(8) C2 .0327(10) .0258(9) .0321(11) .0165(8) .0005(8) .0034(8) C3 .0306(10) .0316(10) .0284(10) .0146(9) .0030(8) .0041(8) C4 .0312(10) .0340(10) .0258(10) .0168(8) .0031(8) .0063(8) C5 .0391(11) .0262(9) .0313(11) .0178(9) .0001(9) .0032(8) C6 .0303(10) .0296(10) .0288(10) .0112(8) .0002(8) -.0001(8) C7 .0488(13) .0400(12) .0511(14) .0138(11) .0131(11) .0029(11) C8 .0438(14) .0483(14) .0534(15) .0136(11) -.0045(11) -.0009(12) C9 .0527(14) .0469(14) .0649(16) .0268(12) .0051(12) .0163(12) C10 .0503(14) .0433(13) .0519(14) .0187(11) -.0096(11) .0051(11) C11 .0563(17) .072(2) .0525(18) .0142(15) -.0165(14) .0012(15) 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 1 -2 1 -3 -1 -1 -2 -1 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 O4 H1 109.3(19) no C7 N1 C8 108.0(2) ? C7 N1 H2 117.7(17) no C8 N1 H2 134.3(17) no C7 N2 C9 108.5(2) ? C7 N2 H4 124.4(17) no C9 N2 H4 127.0(17) no O1 C1 C2 126.34(19) ? O1 C1 C6 115.36(18) ? C2 C1 C6 118.29(17) ? Cl1 C2 C1 117.32(15) ? Cl1 C2 C3 119.69(15) ? C1 C2 C3 122.99(18) ? O2 C3 C2 125.99(18) ? O2 C3 C4 116.69(17) ? C2 C3 C4 117.33(18) ? O3 C4 C3 118.16(18) ? O3 C4 C5 123.64(18) ? C3 C4 C5 118.19(17) ? Cl2 C5 C4 118.45(15) ? Cl2 C5 C6 120.77(16) ? C4 C5 C6 120.76(18) ? O4 C6 C1 115.73(17) ? O4 C6 C5 122.08(19) ? C1 C6 C5 122.19(19) ? N1 C7 N2 108.7(2) ? N1 C7 H3 124.9(15) no N2 C7 H3 126.3(15) no N1 C8 C9 107.8(2) ? N1 C8 H6 124.3(19) no C9 C8 H6 127.9(19) no N2 C9 C8 107.0(2) ? N2 C9 H5 122.6(15) no C8 C9 H5 130.3(15) no N3 C10 C11 179.1(3) ? C10 C11 H7 110(3) no C10 C11 H8 108(3) no C10 C11 H9 106(3) no H7 C11 H8 99(3) no H7 C11 H9 125(4) no H8 C11 H9 110(4) 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 Cl1 C2 . . 1.7350(19) yes Cl2 C5 . . 1.724(2) yes O1 C1 . . 1.253(2) yes O2 C3 . . 1.245(2) yes O3 C4 . . 1.218(2) yes O4 C6 . . 1.329(2) yes O4 H1 . . .86(3) no N1 C7 . . 1.326(3) yes N1 C8 . . 1.354(3) yes N1 H2 . . .94(3) no N2 C7 . . 1.307(3) yes N2 C9 . . 1.365(3) yes N2 H4 . . .95(3) no N3 C10 . . 1.114(3) yes C1 C2 . . 1.397(3) yes C1 C6 . . 1.498(3) yes C2 C3 . . 1.402(3) yes C3 C4 . . 1.549(3) yes C4 C5 . . 1.446(3) yes C5 C6 . . 1.342(3) yes C7 H3 . . .99(2) no C8 C9 . . 1.328(3) yes C8 H6 . . .88(3) no C9 H5 . . .99(3) no C10 C11 . . 1.443(4) yes C11 H7 . . .88(4) no C11 H8 . . .81(3) no C11 H9 . . .91(4) 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 N1 2.703(2) . no O1 N3 3.193(3) . no O1 C4 3.263(3) 2 no O2 N2 2.773(2) 1_454 no O2 C4 3.095(3) 2_554 no O2 C3 3.239(3) 2_554 no O3 N2 2.974(3) 1_454 no O3 C7 3.168(3) 1_454 no O4 N3 2.827(3) . no N2 C1 3.273(3) 2_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 O4 H1 N3 . .86(3) 2.08(3) 2.827(3) 145(3) yes O4 H1 O1 . .86(3) 2.11(3) 2.613(2) 116(2) yes N1 H2 O1 . .94(3) 1.78(3) 2.703(2) 171(3) yes N2 H4 O2 1_656 .95(3) 1.89(3) 2.773(2) 154(2) yes N2 H4 O3 1_656 .95(3) 2.31(3) 2.974(3) 127(2) yes C11 H7 Cl2 1_656 .88(4) 2.81(5) 3.507(4) 136(4) 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 Cl1 C2 C1 O1 -2.3(3) no Cl1 C2 C1 C6 176.31(17) no Cl1 C2 C3 O2 .5(3) no Cl1 C2 C3 C4 -179.34(15) no Cl2 C5 C4 O3 -3.5(3) no Cl2 C5 C4 C3 176.38(16) no Cl2 C5 C6 O4 -.1(3) no Cl2 C5 C6 C1 -179.41(17) no O1 C1 C2 C3 178.2(2) no O1 C1 C6 O4 1.4(3) no O1 C1 C6 C5 -179.2(2) no O2 C3 C2 C1 179.9(2) no O2 C3 C4 O3 4.3(3) no O2 C3 C4 C5 -175.7(2) no O3 C4 C3 C2 -175.9(2) no O3 C4 C5 C6 174.7(2) no O4 C6 C1 C2 -177.4(2) no O4 C6 C5 C4 -178.3(2) no N1 C7 N2 C9 .3(3) no N1 C8 C9 N2 .3(3) no N2 C7 N1 C8 -.1(3) no C1 C2 C3 C4 .1(3) no C1 C6 C5 C4 2.4(4) no C2 C1 C6 C5 2.0(3) no C2 C3 C4 C5 4.2(3) no C3 C2 C1 C6 -3.1(3) no C3 C4 C5 C6 -5.4(3) no C7 N1 C8 C9 -.1(3) no C7 N2 C9 C8 -.3(3) no