#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/86/2228657.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_2228657
loop_
_publ_author_name
'Hu, Jingchun'
'Zhang, Jinfang'
'Zhang, Weiming'
'Zhang, Chi'
_publ_section_title
;
 {2-[6-(1H-Benzimidazol-2-yl-κN³)-2-pyridyl-κN]benzimidazolato-κN}(dicyanamido-κN)(methanol-κO)copper(II)
;
_journal_coeditor_code           BT5405
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m61
_journal_paper_doi               10.1107/S1600536810050178
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C19 H12 N5) (C2 N3) (C H4 O)]'
_chemical_formula_moiety         'C22 H16 Cu N8 O'
_chemical_formula_sum            'C22 H16 Cu N8 O'
_chemical_formula_weight         471.98
_chemical_name_systematic
;
{2-[6-(1H-Benzimidazol-2-yl-κN³)-2-pyridyl-
κN]benzimidazolato-κN}(dicyanamido-κN)(methanol-
κO)copper(II)
;
_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           'SHELXTL (Sheldrick, 2008)'
_cell_angle_alpha                101.74(3)
_cell_angle_beta                 99.03(3)
_cell_angle_gamma                97.12(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8262(14)
_cell_length_b                   12.189(2)
_cell_length_c                   12.609(3)
_cell_measurement_reflns_used    4368
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0485
_cell_measurement_theta_min      3.4597
_cell_volume                     1001.2(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2007)'
_computing_data_collection       'CrystalClear (Rigaku, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7787
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2007)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             482
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0326P)²+0.7506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                3294
_reflns_number_total             3591
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5405.cif
_cod_data_source_block           I
_cod_database_code               2228657
_cod_database_fobs_code          2228657
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.40402(4) 0.04545(2) 0.20901(2) 0.01736(10) Uani d . 1 . .
O O1 0.1127(2) 0.03746(13) 0.27080(12) 0.0254(4) Uani d . 1 . .
H H1 0.0241 0.0546 0.2282 0.030 Uiso d R 1 . .
N N1 0.3511(3) 0.14654(14) 0.10718(14) 0.0168(4) Uani d . 1 . .
N N2 0.5225(3) 0.19964(14) 0.31068(14) 0.0196(4) Uani d . 1 . .
N N3 0.5742(3) 0.38708(14) 0.32891(15) 0.0225(4) Uani d . 1 . .
H H3A 0.5719 0.4521 0.3125 0.027 Uiso d R 1 . .
N N4 0.2876(3) -0.06889(14) 0.06878(14) 0.0178(4) Uani d . 1 . .
N N5 0.1565(3) -0.09661(14) -0.11513(14) 0.0188(4) Uani d . 1 . .
N N6 0.5284(3) -0.05076(15) 0.29717(15) 0.0246(4) Uani d . 1 . .
N N7 0.7320(3) -0.19234(16) 0.34181(17) 0.0307(5) Uani d . 1 . .
N N8 0.6356(4) -0.39938(18) 0.2773(2) 0.0430(6) Uani d . 1 . .
C C1 0.2400(3) -0.18446(17) 0.02561(17) 0.0171(4) Uani d . 1 . .
C C2 0.2565(3) -0.27628(17) 0.07551(19) 0.0203(5) Uani d . 1 . .
H H2A 0.3067 -0.2652 0.1505 0.024 Uiso calc R 1 . .
C C3 0.1956(3) -0.38377(18) 0.0091(2) 0.0247(5) Uani d . 1 . .
H H3B 0.2048 -0.4464 0.0401 0.030 Uiso calc R 1 . .
C C4 0.1200(3) -0.40094(19) -0.1044(2) 0.0260(5) Uani d . 1 . .
H H4A 0.0827 -0.4747 -0.1469 0.031 Uiso calc R 1 . .
C C5 0.0996(3) -0.31132(19) -0.15430(19) 0.0238(5) Uani d . 1 . .
H H5B 0.0478 -0.3233 -0.2292 0.029 Uiso calc R 1 . .
C C6 0.1599(3) -0.20125(17) -0.08783(17) 0.0181(4) Uani d . 1 . .
C C7 0.2323(3) -0.02371(17) -0.01919(17) 0.0166(4) Uani d . 1 . .
C C8 0.2646(3) 0.10090(17) 0.00213(17) 0.0172(4) Uani d . 1 . .
C C9 0.2181(3) 0.17004(18) -0.07045(18) 0.0203(5) Uani d . 1 . .
H H9A 0.1545 0.1389 -0.1431 0.024 Uiso calc R 1 . .
C C10 0.2695(3) 0.28666(18) -0.03130(19) 0.0225(5) Uani d . 1 . .
H H10A 0.2409 0.3345 -0.0785 0.027 Uiso calc R 1 . .
C C11 0.3629(3) 0.33284(18) 0.07713(19) 0.0211(5) Uani d . 1 . .
H H11A 0.3985 0.4110 0.1033 0.025 Uiso calc R 1 . .
C C12 0.4016(3) 0.25952(17) 0.14528(18) 0.0185(5) Uani d . 1 . .
C C13 0.4982(3) 0.28491(17) 0.26130(18) 0.0186(5) Uani d . 1 . .
C C14 0.6564(3) 0.36794(18) 0.42919(19) 0.0240(5) Uani d . 1 . .
C C15 0.7569(4) 0.4417(2) 0.5265(2) 0.0351(6) Uani d . 1 . .
H H15A 0.7786 0.5200 0.5337 0.042 Uiso calc R 1 . .
C C16 0.8230(4) 0.3930(2) 0.6122(2) 0.0400(7) Uani d . 1 . .
H H16A 0.8917 0.4398 0.6788 0.048 Uiso calc R 1 . .
C C17 0.7900(4) 0.2751(2) 0.6023(2) 0.0343(6) Uani d . 1 . .
H H17A 0.8374 0.2457 0.6621 0.041 Uiso calc R 1 . .
C C18 0.6886(4) 0.2019(2) 0.50539(19) 0.0272(5) Uani d . 1 . .
H H18A 0.6655 0.1238 0.4991 0.033 Uiso calc R 1 . .
C C19 0.6224(3) 0.24939(18) 0.41759(18) 0.0209(5) Uani d . 1 . .
C C20 0.6166(3) -0.12164(18) 0.31518(17) 0.0205(5) Uani d . 1 . .
C C21 0.6717(4) -0.3023(2) 0.3061(2) 0.0273(5) Uani d . 1 . .
C C22 0.1031(4) 0.0833(2) 0.3824(2) 0.0383(6) Uani d . 1 . .
H H22A 0.1013 0.1634 0.3931 0.057 Uiso calc R 1 . .
H H22B 0.2185 0.0705 0.4297 0.057 Uiso calc R 1 . .
H H22C -0.0169 0.0470 0.3999 0.057 Uiso calc R 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'
Cu Cu 0.3201 1.2651 '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'
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
_geom_angle_publ_flag
N6 Cu1 N1 . . 164.13(8) ?
N6 Cu1 N4 . . 100.45(8) ?
N1 Cu1 N4 . . 79.51(7) ?
N6 Cu1 N2 . . 98.73(8) ?
N1 Cu1 N2 . . 79.36(7) ?
N4 Cu1 N2 . . 158.46(7) ?
N6 Cu1 O1 . . 97.03(7) ?
N1 Cu1 O1 . . 98.82(7) ?
N4 Cu1 O1 . . 93.63(7) ?
N2 Cu1 O1 . . 93.64(7) ?
C22 O1 Cu1 . . 122.14(14) ?
C22 O1 H1 . . 111.5 ?
Cu1 O1 H1 . . 111.4 ?
C8 N1 C12 . . 121.54(18) ?
C8 N1 Cu1 . . 119.15(14) ?
C12 N1 Cu1 . . 119.31(14) ?
C13 N2 C19 . . 105.85(17) ?
C13 N2 Cu1 . . 112.46(14) ?
C19 N2 Cu1 . . 141.69(15) ?
C13 N3 C14 . . 107.20(18) ?
C13 N3 H3A . . 126.4 ?
C14 N3 H3A . . 126.4 ?
C7 N4 C1 . . 103.53(17) ?
C7 N4 Cu1 . . 114.48(13) ?
C1 N4 Cu1 . . 141.98(15) ?
C7 N5 C6 . . 102.69(17) ?
C20 N6 Cu1 . . 156.97(18) ?
C20 N7 C21 . . 120.2(2) ?
N4 C1 C2 . . 131.1(2) ?
N4 C1 C6 . . 107.57(18) ?
C2 C1 C6 . . 121.29(19) ?
C3 C2 C1 . . 117.4(2) ?
C3 C2 H2A . . 121.3 ?
C1 C2 H2A . . 121.3 ?
C2 C3 C4 . . 121.5(2) ?
C2 C3 H3B . . 119.2 ?
C4 C3 H3B . . 119.2 ?
C5 C4 C3 . . 121.7(2) ?
C5 C4 H4A . . 119.1 ?
C3 C4 H4A . . 119.1 ?
C4 C5 C6 . . 117.5(2) ?
C4 C5 H5B . . 121.2 ?
C6 C5 H5B . . 121.2 ?
N5 C6 C5 . . 130.0(2) ?
N5 C6 C1 . . 109.42(18) ?
C5 C6 C1 . . 120.6(2) ?
N5 C7 N4 . . 116.78(18) ?
N5 C7 C8 . . 127.12(19) ?
N4 C7 C8 . . 116.10(18) ?
N1 C8 C9 . . 120.47(19) ?
N1 C8 C7 . . 110.70(18) ?
C9 C8 C7 . . 128.83(19) ?
C10 C9 C8 . . 118.1(2) ?
C10 C9 H9A . . 121.0 ?
C8 C9 H9A . . 121.0 ?
C11 C10 C9 . . 120.9(2) ?
C11 C10 H10A . . 119.6 ?
C9 C10 H10A . . 119.6 ?
C12 C11 C10 . . 118.1(2) ?
C12 C11 H11A . . 121.0 ?
C10 C11 H11A . . 121.0 ?
N1 C12 C11 . . 120.9(2) ?
N1 C12 C13 . . 109.69(18) ?
C11 C12 C13 . . 129.39(19) ?
N2 C13 N3 . . 112.53(19) ?
N2 C13 C12 . . 119.10(18) ?
N3 C13 C12 . . 128.36(19) ?
N3 C14 C15 . . 131.6(2) ?
N3 C14 C19 . . 106.14(19) ?
C15 C14 C19 . . 122.3(2) ?
C16 C15 C14 . . 116.4(2) ?
C16 C15 H15A . . 121.8 ?
C14 C15 H15A . . 121.8 ?
C15 C16 C17 . . 122.1(2) ?
C15 C16 H16A . . 118.9 ?
C17 C16 H16A . . 118.9 ?
C18 C17 C16 . . 121.3(2) ?
C18 C17 H17A . . 119.4 ?
C16 C17 H17A . . 119.4 ?
C17 C18 C19 . . 117.5(2) ?
C17 C18 H18A . . 121.3 ?
C19 C18 H18A . . 121.3 ?
N2 C19 C18 . . 131.3(2) ?
N2 C19 C14 . . 108.28(19) ?
C18 C19 C14 . . 120.5(2) ?
N6 C20 N7 . . 173.5(2) ?
N8 C21 N7 . . 174.3(3) ?
O1 C22 H22A . . 109.5 ?
O1 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O1 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 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
Cu1 N6 . 1.9528(19) ?
Cu1 N1 . 1.9763(18) ?
Cu1 N4 . 1.9955(19) ?
Cu1 N2 . 2.0364(19) ?
Cu1 O1 . 2.2452(16) ?
O1 C22 . 1.420(3) ?
O1 H1 . 0.8200 ?
N1 C8 . 1.336(3) ?
N1 C12 . 1.344(3) ?
N2 C13 . 1.330(3) ?
N2 C19 . 1.388(3) ?
N3 C13 . 1.348(3) ?
N3 C14 . 1.378(3) ?
N3 H3A . 0.8601 ?
N4 C7 . 1.358(3) ?
N4 C1 . 1.380(3) ?
N5 C7 . 1.331(3) ?
N5 C6 . 1.389(3) ?
N6 C20 . 1.151(3) ?
N7 C20 . 1.296(3) ?
N7 C21 . 1.315(3) ?
N8 C21 . 1.148(3) ?
C1 C2 . 1.399(3) ?
C1 C6 . 1.412(3) ?
C2 C3 . 1.378(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.406(3) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.378(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.403(3) ?
C5 H5B . 0.9300 ?
C7 C8 . 1.470(3) ?
C8 C9 . 1.392(3) ?
C9 C10 . 1.387(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.384(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.381(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.461(3) ?
C14 C15 . 1.386(3) ?
C14 C19 . 1.408(3) ?
C15 C16 . 1.377(4) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.404(4) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.380(3) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.390(3) ?
C18 H18A . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
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
O1 H1 N5 2 0.82 1.93 2.743(3) 172.0
N3 H3A N8 1_565 0.86 1.96 2.807(3) 166.3
