#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/70/2217054.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_2217054
loop_
_publ_author_name
'Xia, Xian-you'
'Zhang, Yong'
'Qu, Yuan'
'Chen, Xue-mei'
'Liu, Ting'
_publ_section_title
;
 Bis[bis(1H-benzimidazol-2-ylmethyl)amine]copper(II) dichloride
 methanol disolvate dihydrate
;
_journal_coeditor_code           GG2050
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m190
_journal_page_last               m190
_journal_paper_doi               10.1107/S1600536807065816
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C16 H14 N5)2] Cl2, 2C H4 O, 2H2 O'
_chemical_formula_moiety         'C32 H30 Cu N10 2+, 2(Cl -), 2(H2 O)'
_chemical_formula_sum            'C32 H34 Cl2 Cu N10 O2'
_chemical_formula_weight         725.13
_chemical_name_systematic
;
Bis[bis(1H-benzimidazol-2-ylmethyl)amine]copper(II)
dichloride methanol disolvate dihydrate
;
_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                82.095(5)
_cell_angle_beta                 88.441(5)
_cell_angle_gamma                87.073(5)
_cell_formula_units_Z            1
_cell_length_a                   9.653(3)
_cell_length_b                   9.921(3)
_cell_length_c                   10.316(3)
_cell_measurement_reflns_used    3239
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      1.56
_cell_volume                     977.1(5)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0988
_diffrn_reflns_av_sigmaI/netI    0.0890
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9121
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             375
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.596
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0459P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                2937
_reflns_number_total             3799
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2050.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2217054
_cod_database_fobs_code          2217054
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
Cu Cu1 0.5000 0.5000 1.0000 0.02773(17) Uani d S 1
N N1 0.4996(3) 0.5259(2) 0.7434(2) 0.0378(6) Uani d D 1
H H1C 0.530(3) 0.597(2) 0.696(2) 0.045 Uiso d D 1
N N2 0.1441(3) 0.4115(3) 0.8191(3) 0.0434(7) Uani d D 1
H H2 0.106(3) 0.406(4) 0.746(2) 0.052 Uiso d D 1
N N3 0.3091(2) 0.4492(2) 0.9528(2) 0.0337(6) Uani d . 1
N N4 0.6536(3) 0.1732(3) 0.8228(3) 0.0384(6) Uani d D 1
H H4 0.678(3) 0.154(3) 0.7466(17) 0.046 Uiso d D 1
N N5 0.5738(2) 0.3203(2) 0.9531(2) 0.0308(5) Uani d . 1
C C1 0.0971(3) 0.3621(3) 0.9427(3) 0.0410(8) Uani d . 1
C C2 -0.0207(4) 0.2958(4) 0.9870(4) 0.0536(10) Uani d . 1
H H2A -0.0891 0.2804 0.9297 0.064 Uiso calc R 1
C C3 -0.0330(4) 0.2534(4) 1.1187(4) 0.0652(11) Uani d . 1
H H3 -0.1117 0.2092 1.1520 0.078 Uiso calc R 1
C C4 0.0712(4) 0.2759(4) 1.2042(4) 0.0604(10) Uani d . 1
H H4A 0.0607 0.2452 1.2930 0.072 Uiso calc R 1
C C5 0.1892(4) 0.3426(4) 1.1598(3) 0.0467(9) Uani d . 1
H H5 0.2577 0.3575 1.2172 0.056 Uiso calc R 1
C C6 0.2023(3) 0.3866(3) 1.0261(3) 0.0351(7) Uani d . 1
C C7 0.2717(3) 0.4620(3) 0.8288(3) 0.0362(7) Uani d . 1
C C8 0.3527(4) 0.5231(3) 0.7149(3) 0.0467(9) Uani d . 1
H H8A 0.3423 0.4713 0.6428 0.056 Uiso calc R 1
H H8B 0.3164 0.6154 0.6878 0.056 Uiso calc R 1
C C9 0.5817(4) 0.4056(3) 0.7148(3) 0.0472(9) Uani d . 1
H H9A 0.6722 0.4331 0.6808 0.057 Uiso calc R 1
H H9B 0.5365 0.3659 0.6472 0.057 Uiso calc R 1
C C10 0.6004(3) 0.3008(3) 0.8311(3) 0.0332(7) Uani d . 1
C C11 0.6591(3) 0.1038(3) 0.9456(3) 0.0358(7) Uani d . 1
C C12 0.7028(4) -0.0289(3) 0.9947(4) 0.0478(9) Uani d . 1
H H12 0.7384 -0.0894 0.9394 0.057 Uiso calc R 1
C C13 0.6915(4) -0.0673(3) 1.1271(4) 0.0512(9) Uani d . 1
H H13 0.7205 -0.1552 1.1623 0.061 Uiso calc R 1
C C14 0.6370(4) 0.0231(3) 1.2104(3) 0.0465(8) Uani d . 1
H H14 0.6298 -0.0062 1.2998 0.056 Uiso calc R 1
C C15 0.5939(3) 0.1543(3) 1.1627(3) 0.0392(7) Uani d . 1
H H15 0.5565 0.2135 1.2183 0.047 Uiso calc R 1
C C16 0.6075(3) 0.1957(3) 1.0300(3) 0.0307(6) Uani d . 1
Cl Cl1 0.37341(12) 0.23380(10) 0.47316(9) 0.0656(3) Uani d . 1
O O1 0.6586(3) 0.0805(3) 0.5743(3) 0.0720(9) Uani d D 1
H H1B 0.624(5) 0.138(3) 0.520(4) 0.108 Uiso d D 1
H H1A 0.628(5) 0.009(3) 0.588(5) 0.108 Uiso d D 1
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'
Cu Cu 0.3201 1.2651 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N5 Cu1 N5 2_667 . 180.00(13)
N5 Cu1 N3 2_667 2_667 88.03(9)
N5 Cu1 N3 . 2_667 91.97(9)
N5 Cu1 N3 2_667 . 91.97(9)
N5 Cu1 N3 . . 88.03(9)
N3 Cu1 N3 2_667 . 180.00(12)
N5 Cu1 N1 2_667 . 105.57(9)
N5 Cu1 N1 . . 74.43(9)
N3 Cu1 N1 2_667 . 105.76(9)
N3 Cu1 N1 . . 74.24(9)
C9 N1 C8 . . 114.0(2)
C9 N1 Cu1 . . 102.82(18)
C8 N1 Cu1 . . 102.97(19)
C9 N1 H1C . . 109(2)
C8 N1 H1C . . 106(2)
Cu1 N1 H1C . . 122(2)
C7 N2 C1 . . 108.6(2)
C7 N2 H2 . . 124(2)
C1 N2 H2 . . 128(2)
C7 N3 C6 . . 106.4(2)
C7 N3 Cu1 . . 120.7(2)
C6 N3 Cu1 . . 132.5(2)
C10 N4 C11 . . 108.2(2)
C10 N4 H4 . . 118(2)
C11 N4 H4 . . 134(2)
C10 N5 C16 . . 105.9(2)
C10 N5 Cu1 . . 122.1(2)
C16 N5 Cu1 . . 131.95(19)
N2 C1 C2 . . 132.2(3)
N2 C1 C6 . . 104.9(3)
C2 C1 C6 . . 122.8(3)
C3 C2 C1 . . 117.4(3)
C3 C2 H2A . . 121.3
C1 C2 H2A . . 121.3
C2 C3 C4 . . 120.9(4)
C2 C3 H3 . . 119.5
C4 C3 H3 . . 119.5
C5 C4 C3 . . 121.7(4)
C5 C4 H4A . . 119.1
C3 C4 H4A . . 119.1
C4 C5 C6 . . 117.8(3)
C4 C5 H5 . . 121.1
C6 C5 H5 . . 121.1
N3 C6 C5 . . 131.1(3)
N3 C6 C1 . . 109.4(3)
C5 C6 C1 . . 119.4(3)
N3 C7 N2 . . 110.7(3)
N3 C7 C8 . . 126.1(3)
N2 C7 C8 . . 123.2(3)
N1 C8 C7 . . 112.1(3)
N1 C8 H8A . . 109.2
C7 C8 H8A . . 109.2
N1 C8 H8B . . 109.2
C7 C8 H8B . . 109.2
H8A C8 H8B . . 107.9
N1 C9 C10 . . 113.0(3)
N1 C9 H9A . . 109.0
C10 C9 H9A . . 109.0
N1 C9 H9B . . 109.0
C10 C9 H9B . . 109.0
H9A C9 H9B . . 107.8
N5 C10 N4 . . 112.0(3)
N5 C10 C9 . . 125.3(3)
N4 C10 C9 . . 122.7(3)
N4 C11 C12 . . 133.0(3)
N4 C11 C16 . . 106.0(3)
C12 C11 C16 . . 120.9(3)
C13 C12 C11 . . 117.7(3)
C13 C12 H12 . . 121.2
C11 C12 H12 . . 121.2
C12 C13 C14 . . 121.3(3)
C12 C13 H13 . . 119.3
C14 C13 H13 . . 119.3
C15 C14 C13 . . 121.3(3)
C15 C14 H14 . . 119.4
C13 C14 H14 . . 119.4
C14 C15 C16 . . 118.2(3)
C14 C15 H15 . . 120.9
C16 C15 H15 . . 120.9
C15 C16 N5 . . 131.6(3)
C15 C16 C11 . . 120.6(3)
N5 C16 C11 . . 107.8(3)
H1B O1 H1A . . 120(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N1 . 2.624(3)
Cu1 N3 2_667 2.024(2)
Cu1 N3 . 2.024(2)
Cu1 N5 2_667 2.002(2)
Cu1 N5 . 2.002(2)
N1 C9 . 1.459(4)
N1 C8 . 1.459(4)
N1 H1C . 0.855(10)
N2 C7 . 1.365(4)
N2 C1 . 1.375(4)
N2 H2 . 0.858(10)
N3 C7 . 1.326(4)
N3 C6 . 1.384(4)
N4 C10 . 1.354(4)
N4 C11 . 1.357(4)
N4 H4 . 0.860(10)
N5 C10 . 1.316(4)
N5 C16 . 1.402(4)
C1 C2 . 1.378(5)
C1 C6 . 1.400(4)
C2 C3 . 1.370(6)
C2 H2A . 0.9300
C3 C4 . 1.401(5)
C3 H3 . 0.9300
C4 C5 . 1.382(5)
C4 H4A . 0.9300
C5 C6 . 1.392(5)
C5 H5 . 0.9300
C7 C8 . 1.470(5)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.484(5)
C9 H9A . 0.9700
C9 H9B . 0.9700
C11 C12 . 1.393(4)
C11 C16 . 1.408(4)
C12 C13 . 1.369(5)
C12 H12 . 0.9300
C13 C14 . 1.400(5)
C13 H13 . 0.9300
C14 C15 . 1.374(4)
C14 H14 . 0.9300
C15 C16 . 1.379(4)
C15 H15 . 0.9300
O1 H1A . 0.778(17)
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
N4 H4 O1 . 0.860(10) 2.027(15) 2.839(4) 157(3)
O1 H1B Cl1 . 0.81(4) 2.59(4) 3.206(4) 134(5)
N1 H1C Cl1 2_666 0.855(10) 2.455(12) 3.296(3) 168(3)
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
N5 Cu1 N1 C9 2_667 167.82(19)
N5 Cu1 N1 C9 . -12.18(19)
N3 Cu1 N1 C9 2_667 75.4(2)
N3 Cu1 N1 C9 . -104.6(2)
N5 Cu1 N1 C8 2_667 -73.47(19)
N5 Cu1 N1 C8 . 106.53(19)
N3 Cu1 N1 C8 2_667 -165.85(18)
N3 Cu1 N1 C8 . 14.15(18)
N5 Cu1 N3 C7 2_667 100.4(2)
N5 Cu1 N3 C7 . -79.6(2)
N1 Cu1 N3 C7 . -5.3(2)
N5 Cu1 N3 C6 2_667 -87.1(3)
N5 Cu1 N3 C6 . 92.9(3)
N1 Cu1 N3 C6 . 167.3(3)
N3 Cu1 N5 C10 2_667 -99.2(2)
N3 Cu1 N5 C10 . 80.8(2)
N1 Cu1 N5 C10 . 6.6(2)
N3 Cu1 N5 C16 2_667 80.8(2)
N3 Cu1 N5 C16 . -99.2(2)
N1 Cu1 N5 C16 . -173.3(3)
C7 N2 C1 C2 . -176.6(4)
C7 N2 C1 C6 . 0.5(3)
N2 C1 C2 C3 . 176.8(4)
C6 C1 C2 C3 . 0.2(5)
C1 C2 C3 C4 . -0.6(6)
C2 C3 C4 C5 . 0.7(7)
C3 C4 C5 C6 . -0.4(6)
C7 N3 C6 C5 . 176.4(3)
Cu1 N3 C6 C5 . 3.0(5)
C7 N3 C6 C1 . -0.3(3)
Cu1 N3 C6 C1 . -173.7(2)
C4 C5 C6 N3 . -176.5(3)
C4 C5 C6 C1 . -0.1(5)
N2 C1 C6 N3 . -0.1(3)
C2 C1 C6 N3 . 177.3(3)
N2 C1 C6 C5 . -177.2(3)
C2 C1 C6 C5 . 0.2(5)
C6 N3 C7 N2 . 0.6(3)
Cu1 N3 C7 N2 . 174.94(19)
C6 N3 C7 C8 . 179.9(3)
Cu1 N3 C7 C8 . -5.8(4)
C1 N2 C7 N3 . -0.7(4)
C1 N2 C7 C8 . 179.9(3)
C9 N1 C8 C7 . 90.9(3)
Cu1 N1 C8 C7 . -19.7(3)
N3 C7 C8 N1 . 20.5(5)
N2 C7 C8 N1 . -160.3(3)
C8 N1 C9 C10 . -95.4(3)
Cu1 N1 C9 C10 . 15.3(3)
C16 N5 C10 N4 . -2.0(3)
Cu1 N5 C10 N4 . 178.00(18)
C16 N5 C10 C9 . -179.4(3)
Cu1 N5 C10 C9 . 0.7(4)
C11 N4 C10 N5 . 1.6(3)
C11 N4 C10 C9 . 179.0(3)
N1 C9 C10 N5 . -13.7(4)
N1 C9 C10 N4 . 169.2(3)
C10 N4 C11 C12 . 179.4(3)
C10 N4 C11 C16 . -0.4(3)
N4 C11 C12 C13 . -178.7(3)
C16 C11 C12 C13 . 1.1(5)
C11 C12 C13 C14 . 0.5(5)
C12 C13 C14 C15 . -0.6(5)
C13 C14 C15 C16 . -0.9(5)
C14 C15 C16 N5 . 180.0(3)
C14 C15 C16 C11 . 2.5(4)
C10 N5 C16 C15 . -176.0(3)
Cu1 N5 C16 C15 . 3.9(5)
C10 N5 C16 C11 . 1.7(3)
Cu1 N5 C16 C11 . -178.31(18)
N4 C11 C16 C15 . 177.2(3)
C12 C11 C16 C15 . -2.6(4)
N4 C11 C16 N5 . -0.8(3)
C12 C11 C16 N5 . 179.3(3)
