#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/27/8102711.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102711
loop_
_publ_author_name
Wei-Qiu
_publ_section_title
;
 Crystal structure of
 aqua(2-(2pyridyl)benzimidazole)-(methanedisulfonato)copper(II),
 Cu(H2O)(C12H8N3)[CH2(SO3)2]
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              353
_journal_volume                  225
_journal_year                    2010
_chemical_formula_moiety         'C13 H12 Cu N3 O7 S2'
_chemical_formula_sum            'C13 H12 Cu N3 O7 S2'
_chemical_formula_weight         449.92
_chemical_melting_point          ?
_chemical_name_systematic
;
Crystal structure of
aqua-(2-(2-pyridyl)benzimidazole)copper(II)methanedisulfonate,Cu(H₂O)\
(C₁₂H₈N₃)[CH₂(SO₃)₂]

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.022(5)
_cell_angle_beta                 99.214(5)
_cell_angle_gamma                101.017(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9522(4)
_cell_length_b                   11.2534(6)
_cell_length_c                   11.4833(7)
_cell_measurement_reflns_used    2976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2181
_cell_measurement_theta_min      3.0665
_cell_volume                     809.40(9)
_computing_cell_refinement       CrysAlis
_computing_data_collection       'CrysAlis [1]'
_computing_data_reduction        CrysAlis
_computing_structure_refinement  'SHELXL-97 [3](Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5630
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.28
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    1.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94398
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0278(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0303
_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/[σ²(Fo²)+(0.0313P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0675
_reflns_number_gt                2708
_reflns_number_total             3639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2989.cff
_cod_data_source_block           kan
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        809.39(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102711
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.26586(4) -0.19871(3) 0.15540(3) 0.02641(11) Uani 1 1 d . . .
S2 S -0.22990(8) -0.24862(6) 0.20413(6) 0.02807(16) Uani 1 1 d . . .
S1 S 0.15090(9) -0.18638(6) 0.40846(6) 0.02922(16) Uani 1 1 d . . .
O1 O -0.3595(2) -0.16943(15) 0.17389(18) 0.0335(4) Uani 1 1 d . . .
O5 O 0.1146(2) -0.32609(15) 0.37021(18) 0.0357(4) Uani 1 1 d . . .
O2 O -0.3438(2) -0.36772(16) 0.2093(2) 0.0419(5) Uani 1 1 d . . .
O6 O 0.2861(2) -0.13469(15) 0.33943(16) 0.0317(4) Uani 1 1 d . . .
O3 O -0.0906(2) -0.26838(18) 0.12274(18) 0.0399(5) Uani 1 1 d . . .
OW O 0.2594(2) -0.37795(17) 0.15155(18) 0.0323(4) Uani 1 1 d D . .
O4 O 0.2150(3) -0.11352(17) 0.54201(18) 0.0416(5) Uani 1 1 d . . .
C10 C 0.2000(4) -0.2866(2) -0.2863(3) 0.0348(6) Uani 1 1 d . . .
H10 H 0.1875 -0.3003 -0.3719 0.042 Uiso 1 1 calc R . .
N2 N 0.2570(3) 0.09081(18) 0.0229(2) 0.0285(5) Uani 1 1 d . . .
C13 C -0.0830(4) -0.1525(2) 0.3606(3) 0.0349(6) Uani 1 1 d . . .
H13A H -0.1646 -0.1625 0.4195 0.042 Uiso 1 1 calc R . .
H13B H -0.0550 -0.0619 0.3690 0.042 Uiso 1 1 calc R . .
C5 C 0.2868(4) 0.3078(2) 0.1947(3) 0.0377(7) Uani 1 1 d . . .
H5 H 0.2758 0.3556 0.1426 0.045 Uiso 1 1 calc R . .
C6 C 0.2778(3) 0.1755(2) 0.1456(3) 0.0284(6) Uani 1 1 d . . .
N3 N 0.2356(3) -0.24860(17) -0.03232(19) 0.0251(4) Uani 1 1 d . . .
C7 C 0.2597(3) -0.0261(2) 0.0313(2) 0.0251(5) Uani 1 1 d . . .
C11 C 0.1973(4) -0.3885(2) -0.2442(3) 0.0344(6) Uani 1 1 d . . .
H11 H 0.1833 -0.4719 -0.3015 0.041 Uiso 1 1 calc R . .
N1 N 0.2799(3) -0.02396(17) 0.1476(2) 0.0257(4) Uani 1 1 d . . .
C9 C 0.2215(3) -0.1636(2) -0.1989(3) 0.0301(6) Uani 1 1 d . . .
H9 H 0.2245 -0.0928 -0.2242 0.036 Uiso 1 1 calc R . .
C4 C 0.3125(4) 0.3639(3) 0.3228(3) 0.0445(7) Uani 1 1 d . . .
H4 H 0.3168 0.4517 0.3583 0.053 Uiso 1 1 calc R . .
C1 C 0.2937(3) 0.1029(2) 0.2244(2) 0.0265(5) Uani 1 1 d . . .
C8 C 0.2383(3) -0.1486(2) -0.0744(2) 0.0251(5) Uani 1 1 d . . .
C12 C 0.2151(3) -0.3669(2) -0.1186(3) 0.0307(6) Uani 1 1 d . . .
H12 H 0.2129 -0.4366 -0.0918 0.037 Uiso 1 1 calc R . .
C3 C 0.3326(4) 0.2930(3) 0.4026(3) 0.0434(7) Uani 1 1 d . . .
H3 H 0.3514 0.3350 0.4895 0.052 Uiso 1 1 calc R . .
C2 C 0.3250(4) 0.1623(2) 0.3544(3) 0.0370(6) Uani 1 1 d . . .
H2 H 0.3403 0.1157 0.4075 0.044 Uiso 1 1 calc R . .
H1B H 0.378(2) -0.386(3) 0.160(3) 0.056 Uiso 1 1 d D . .
H1A H 0.204(3) -0.384(3) 0.211(2) 0.056 Uiso 1 1 d D . .
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'
Cu Cu 0.3201 1.2651 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cu N1 92.79(8) . . ?
O6 Cu OW 91.12(7) . . ?
N1 Cu OW 175.72(8) . . ?
O6 Cu N3 174.36(7) . . ?
N1 Cu N3 81.99(8) . . ?
OW Cu N3 94.17(7) . . ?
O6 Cu O3 88.39(6) . . ?
N1 Cu O3 97.51(7) . . ?
OW Cu O3 84.33(7) . . ?
N3 Cu O3 90.18(7) . . ?
O2 S2 O3 113.69(11) . . ?
O2 S2 O1 112.32(9) . . ?
O3 S2 O1 111.75(11) . . ?
O2 S2 C13 106.86(12) . . ?
O3 S2 C13 107.02(11) . . ?
O1 S2 C13 104.50(11) . . ?
O4 S1 O5 115.96(10) . . ?
O4 S1 O6 111.38(10) . . ?
O5 S1 O6 111.48(10) . . ?
O4 S1 C13 104.50(12) . . ?
O5 S1 C13 107.66(11) . . ?
O6 S1 C13 104.94(11) . . ?
S1 O6 Cu 127.84(10) . . ?
S2 O3 Cu 134.45(11) . . ?
Cu OW H1B 108.3(19) . . ?
Cu OW H1A 104.7(19) . . ?
H1B OW H1A 115.2(17) . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C7 N2 C6 105.92(19) . . ?
S2 C13 S1 117.11(15) . . ?
S2 C13 H13A 108.0 . . ?
S1 C13 H13A 108.0 . . ?
S2 C13 H13B 108.0 . . ?
S1 C13 H13B 108.0 . . ?
H13A C13 H13B 107.3 . . ?
C4 C5 C6 116.9(2) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
N2 C6 C5 131.7(2) . . ?
N2 C6 C1 106.8(2) . . ?
C5 C6 C1 121.6(3) . . ?
C12 N3 C8 117.5(2) . . ?
C12 N3 Cu 127.71(16) . . ?
C8 N3 Cu 114.82(16) . . ?
N1 C7 N2 113.3(2) . . ?
N1 C7 C8 120.09(19) . . ?
N2 C7 C8 126.6(2) . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C7 N1 C1 106.55(18) . . ?
C7 N1 Cu 112.28(15) . . ?
C1 N1 Cu 141.04(17) . . ?
C8 C9 C10 118.4(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C2 C1 N1 131.8(2) . . ?
C2 C1 C6 120.6(2) . . ?
N1 C1 C6 107.5(2) . . ?
N3 C8 C9 123.2(2) . . ?
N3 C8 C7 110.8(2) . . ?
C9 C8 C7 126.0(2) . . ?
N3 C12 C11 122.3(2) . . ?
N3 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C2 C1 117.6(2) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu O6 1.9694(18) . ?
Cu N1 1.9821(17) . ?
Cu OW 1.9948(16) . ?
Cu N3 2.007(2) . ?
Cu O3 2.3803(16) . ?
S2 O2 1.4447(16) . ?
S2 O3 1.4482(18) . ?
S2 O1 1.4614(16) . ?
S2 C13 1.779(3) . ?
S1 O4 1.4299(19) . ?
S1 O5 1.4461(16) . ?
S1 O6 1.4765(17) . ?
S1 C13 1.783(2) . ?
OW H1B 0.843(9) . ?
OW H1A 0.848(9) . ?
C10 C11 1.381(3) . ?
C10 C9 1.383(4) . ?
C10 H10 0.9300 . ?
N2 C7 1.354(3) . ?
N2 C6 1.386(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C5 C4 1.364(4) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.409(3) . ?
N3 C12 1.340(3) . ?
N3 C8 1.360(3) . ?
C7 N1 1.312(3) . ?
C7 C8 1.473(3) . ?
C11 C12 1.363(4) . ?
C11 H11 0.9300 . ?
N1 C1 1.388(3) . ?
C9 C8 1.367(3) . ?
C9 H9 0.9300 . ?
C4 C3 1.405(4) . ?
C4 H4 0.9300 . ?
C1 C2 1.383(4) . ?
C12 H12 0.9300 . ?
C3 C2 1.380(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 S1 O6 Cu -179.94(11) . . . . ?
O5 S1 O6 Cu 48.82(15) . . . . ?
C13 S1 O6 Cu -67.44(15) . . . . ?
N1 Cu O6 S1 127.55(13) . . . . ?
OW Cu O6 S1 -54.20(13) . . . . ?
N3 Cu O6 S1 105.4(7) . . . . ?
O3 Cu O6 S1 30.10(13) . . . . ?
O2 S2 O3 Cu -119.20(15) . . . . ?
O1 S2 O3 Cu 112.37(15) . . . . ?
C13 S2 O3 Cu -1.45(19) . . . . ?
O6 Cu O3 S2 9.96(15) . . . . ?
N1 Cu O3 S2 -82.64(16) . . . . ?
OW Cu O3 S2 101.24(16) . . . . ?
N3 Cu O3 S2 -164.59(16) . . . . ?
O2 S2 C13 S1 83.26(16) . . . . ?
O3 S2 C13 S1 -38.87(18) . . . . ?
O1 S2 C13 S1 -157.51(13) . . . . ?
O4 S1 C13 S2 -169.51(14) . . . . ?
O5 S1 C13 S2 -45.68(18) . . . . ?
O6 S1 C13 S2 73.19(17) . . . . ?
C7 N2 C6 C5 179.4(2) . . . . ?
C7 N2 C6 C1 0.4(2) . . . . ?
C4 C5 C6 N2 -178.7(2) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
O6 Cu N3 C12 -158.3(6) . . . . ?
N1 Cu N3 C12 179.4(2) . . . . ?
OW Cu N3 C12 1.3(2) . . . . ?
O3 Cu N3 C12 -83.05(19) . . . . ?
O6 Cu N3 C8 22.3(8) . . . . ?
N1 Cu N3 C8 -0.04(15) . . . . ?
OW Cu N3 C8 -178.15(15) . . . . ?
O3 Cu N3 C8 97.52(15) . . . . ?
C6 N2 C7 N1 0.1(3) . . . . ?
C6 N2 C7 C8 178.7(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
N2 C7 N1 C1 -0.5(3) . . . . ?
C8 C7 N1 C1 -179.22(18) . . . . ?
N2 C7 N1 Cu 176.37(14) . . . . ?
C8 C7 N1 Cu -2.4(3) . . . . ?
O6 Cu N1 C7 -176.57(15) . . . . ?
OW Cu N1 C7 27.5(11) . . . . ?
N3 Cu N1 C7 1.29(15) . . . . ?
O3 Cu N1 C7 -87.83(16) . . . . ?
O6 Cu N1 C1 -1.4(2) . . . . ?
OW Cu N1 C1 -157.3(9) . . . . ?
N3 Cu N1 C1 176.5(2) . . . . ?
O3 Cu N1 C1 87.4(2) . . . . ?
C11 C10 C9 C8 -0.3(4) . . . . ?
C6 C5 C4 C3 1.1(4) . . . . ?
C7 N1 C1 C2 -176.8(2) . . . . ?
Cu N1 C1 C2 7.8(4) . . . . ?
C7 N1 C1 C6 0.7(2) . . . . ?
Cu N1 C1 C6 -174.67(17) . . . . ?
N2 C6 C1 C2 177.2(2) . . . . ?
C5 C6 C1 C2 -1.9(3) . . . . ?
N2 C6 C1 N1 -0.7(2) . . . . ?
C5 C6 C1 N1 -179.8(2) . . . . ?
C12 N3 C8 C9 -0.1(3) . . . . ?
Cu N3 C8 C9 179.41(17) . . . . ?
C12 N3 C8 C7 179.44(19) . . . . ?
Cu N3 C8 C7 -1.1(2) . . . . ?
C10 C9 C8 N3 0.2(3) . . . . ?
C10 C9 C8 C7 -179.2(2) . . . . ?
N1 C7 C8 N3 2.3(3) . . . . ?
N2 C7 C8 N3 -176.2(2) . . . . ?
N1 C7 C8 C9 -178.2(2) . . . . ?
N2 C7 C8 C9 3.3(4) . . . . ?
C8 N3 C12 C11 0.0(3) . . . . ?
Cu N3 C12 C11 -179.45(17) . . . . ?
C10 C11 C12 N3 0.0(4) . . . . ?
C5 C4 C3 C2 -0.7(4) . . . . ?
C4 C3 C2 C1 -1.0(4) . . . . ?
N1 C1 C2 C3 179.5(2) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
