#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204420.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_2204420 loop_ _publ_author_name 'Ishida, Hiroyuki' _publ_section_title ; Bis(3-picolinium) chloranilate dihydrate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1900 _journal_page_last o1901 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac '2C6 H8 N 1+, C6 Cl2 O4 2-, 2H2 O' _chemical_formula_moiety '2C6 H8 N 1+, C6 Cl2 O4 2-, 2H2 O' _chemical_formula_sum 'C18 H20 Cl2 N2 O6' _chemical_formula_weight 431.27 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 98.52(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.212(6) _cell_length_b 7.349(2) _cell_length_c 15.045(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 301 _cell_measurement_theta_max 12.0 _cell_measurement_theta_min 11.6 _cell_volume 1007.3(8) _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_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 301 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'Rigaku AFC-5R' _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 0.71073 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 3034 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.74 _diffrn_standards_decay_% 0.90 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 448.00 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.182 _refine_diff_density_min -0.208 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 2320 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.00 _refine_ls_R_factor_all 0.081 _refine_ls_R_factor_gt 0.038 _refine_ls_shift/su_max 0.01 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.191P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.090 _refine_ls_wR_factor_ref 0.104 _reflns_number_gt 1521 _reflns_number_total 2320 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ww6295.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _[local]_cod_chemical_formula_sum_orig 'C18 H20 Cl2 N2 O6 ' _cod_original_cell_volume 1007.4(8) _cod_database_code 2204420 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_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cl 0.51250(6) 0.47787(9) 0.29090(3) 0.0571(2) Uani d . 1 Cl O1 0.25959(15) 0.3953(2) 0.38805(9) 0.0546(4) Uani d . 1 O O2 0.74710(15) 0.6000(2) 0.43714(9) 0.0527(4) Uani d . 1 O O3 0.8470(2) 0.7181(3) 0.27802(13) 0.0737(6) Uani d . 1 O N 0.0011(2) 0.2695(3) 0.46111(14) 0.0521(5) Uani d . 1 N C1 0.3751(2) 0.4425(3) 0.43616(12) 0.0377(4) Uani d . 1 C C2 0.5061(2) 0.4892(3) 0.40537(12) 0.0384(4) Uani d . 1 C C3 0.62987(19) 0.5501(2) 0.46204(12) 0.0371(4) Uani d . 1 C C4 -0.0661(2) 0.2227(3) 0.53024(15) 0.0513(5) Uani d . 1 C C5 -0.2008(2) 0.1392(3) 0.51637(16) 0.0517(5) Uani d . 1 C C6 -0.2613(2) 0.1055(3) 0.42840(17) 0.0598(6) Uani d . 1 C C7 -0.1900(3) 0.1568(4) 0.35898(17) 0.0656(7) Uani d . 1 C C8 -0.0573(2) 0.2402(3) 0.37649(16) 0.0598(6) Uani d . 1 C C9 -0.2769(3) 0.0863(4) 0.5940(2) 0.0837(9) Uani d . 1 C H1 0.082(3) 0.317(4) 0.470(2) 0.091(10) Uiso d . 1 H H2 -0.0212 0.2470 0.5886 0.062 Uiso calc R 1 H H3 -0.3516 0.0472 0.4162 0.072 Uiso calc R 1 H H4 -0.2322 0.1347 0.2999 0.079 Uiso calc R 1 H H5 -0.0081 0.2763 0.3297 0.072 Uiso calc R 1 H H6 -0.2935 -0.0427 0.5928 0.126 Uiso calc R 1 H H7 -0.3692 0.1487 0.5895 0.126 Uiso calc R 1 H H8 -0.2167 0.1190 0.6493 0.126 Uiso calc R 1 H H9 0.798(4) 0.688(4) 0.313(2) 0.097(12) Uiso d . 1 H H10 0.791(4) 0.760(5) 0.229(2) 0.118(12) Uiso d . 1 H 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 0.0461(3) 0.0881(4) 0.0362(2) -0.0046(3) 0.00284(19) -0.0016(3) O1 0.0370(8) 0.0807(11) 0.0441(8) -0.0147(7) -0.0003(6) -0.0105(7) O2 0.0365(7) 0.0772(10) 0.0445(8) -0.0148(7) 0.0061(6) 0.0006(7) O3 0.0506(10) 0.1230(17) 0.0471(9) -0.0085(11) 0.0061(8) 0.0177(10) N 0.0299(9) 0.0521(11) 0.0722(12) -0.0031(8) 0.0004(8) -0.0028(9) C1 0.0318(9) 0.0388(10) 0.0409(9) -0.0001(8) -0.0002(7) -0.0032(8) C2 0.0334(9) 0.0461(11) 0.0347(8) 0.0009(8) 0.0016(7) -0.0009(8) C3 0.0311(9) 0.0386(10) 0.0411(9) 0.0007(8) 0.0038(7) 0.0013(8) C4 0.0481(12) 0.0491(12) 0.0528(12) 0.0078(10) -0.0052(10) -0.0030(10) C5 0.0444(12) 0.0426(12) 0.0688(14) 0.0075(9) 0.0110(10) 0.0086(10) C6 0.0355(11) 0.0599(14) 0.0810(17) -0.0095(10) -0.0009(11) -0.0009(12) C7 0.0504(13) 0.0836(18) 0.0581(14) -0.0012(13) -0.0072(11) -0.0083(13) C8 0.0470(12) 0.0737(16) 0.0605(14) 0.0011(12) 0.0139(10) 0.0036(12) C9 0.091(2) 0.0755(18) 0.093(2) 0.0147(16) 0.0416(17) 0.0241(16) 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 0 -4 2 2 2 2 2 -2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle H9 O3 H10 . 110(3) C8 N C4 . 122.6(2) C8 N H1 . 117(2) C4 N H1 . 120(2) O1 C1 C2 . 125.56(18) O1 C1 C3 3_666 116.07(16) C2 C1 C3 3_666 118.37(16) C3 C2 C1 . 123.00(17) C3 C2 Cl . 118.59(15) C1 C2 Cl . 118.38(14) O2 C3 C2 . 125.19(18) O2 C3 C1 3_666 116.25(16) C2 C3 C1 3_666 118.56(16) N C4 C5 . 120.7(2) N C4 H2 . 119.6 C5 C4 H2 . 119.6 C4 C5 C6 . 117.0(2) C4 C5 C9 . 120.9(2) C6 C5 C9 . 122.1(2) C7 C6 C5 . 120.8(2) C7 C6 H3 . 119.6 C5 C6 H3 . 119.6 C8 C7 C6 . 119.8(2) C8 C7 H4 . 120.1 C6 C7 H4 . 120.1 N C8 C7 . 119.1(2) N C8 H5 . 120.5 C7 C8 H5 . 120.5 C5 C9 H6 . 109.5 C5 C9 H7 . 109.5 H6 C9 H7 . 109.5 C5 C9 H8 . 109.5 H6 C9 H8 . 109.5 H7 C9 H8 . 109.5 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 Cl C2 . 1.7339(19) yes O1 C1 . 1.244(2) yes O2 C3 . 1.249(2) yes O3 H9 . 0.77(3) ? O3 H10 . 0.88(4) ? N C8 . 1.324(3) yes N C4 . 1.332(3) yes N H1 . 0.81(3) ? C1 C2 . 1.398(3) yes C1 C3 3_666 1.540(3) yes C2 C3 . 1.392(3) yes C3 C1 3_666 1.540(3) ? C4 C5 . 1.372(3) ? C4 H2 . 0.93 ? C5 C6 . 1.380(3) ? C5 C9 . 1.499(3) yes C6 C7 . 1.367(3) ? C6 H3 . 0.93 ? C7 C8 . 1.358(3) ? C7 H4 . 0.93 ? C8 H5 . 0.93 ? C9 H6 . 0.96 ? C9 H7 . 0.96 ? C9 H8 . 0.96 ? 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 O3 2.859(3) 2_645 no O1 N 2.917(3) . no O1 C8 3.115(3) . no O2 N 2.755(3) 3_666 no O2 O3 2.826(3) . no O2 C4 3.185(3) 3_666 no O2 C8 3.400(3) 1_655 no O3 C8 3.243(4) 2_655 no O3 C4 3.295(4) 3_666 no C3 C5 3.441(3) 1_655 no C3 C6 3.477(3) 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 N H1 O1 . 0.82(3) 2.26(3) 2.917(3) 137(3) yes N H1 O2 3_666 0.82(3) 2.04(3) 2.755(3) 147(3) yes O3 H9 O2 . 0.78(3) 2.09(3) 2.826(3) 158(3) yes O3 H10 O1 2_655 0.89(3) 2.02(3) 2.859(3) 158(3) yes C4 H2 O3 3_666 0.93 2.39 3.295(4) 164 yes C8 H5 O3 2_645 0.93 2.39 3.243(4) 152 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion O1 C1 C2 C3 . . 176.56(19) C3 C1 C2 C3 3_666 . -3.1(3) O1 C1 C2 Cl . . -1.2(3) C3 C1 C2 Cl 3_666 . 179.16(13) C1 C2 C3 O2 . . -177.06(19) Cl C2 C3 O2 . . 0.7(3) C1 C2 C3 C1 . 3_666 3.1(3) Cl C2 C3 C1 . 3_666 -179.16(13) C8 N C4 C5 . . 0.6(3) N C4 C5 C6 . . 0.5(3) N C4 C5 C9 . . -180.0(2) C4 C5 C6 C7 . . -1.1(3) C9 C5 C6 C7 . . 179.4(2) C5 C6 C7 C8 . . 0.7(4) C4 N C8 C7 . . -1.0(4) C6 C7 C8 N . . 0.4(4)