#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/51/2225111.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_2225111
loop_
_publ_author_name
'Zhou, Yan-Ling'
'Liang, Hong'
'Zeng, Ming-Hua'
_publ_section_title
;Bis[(1-methyl-1H-benzimidazol-2-yl)methanol-κ²N³,O]bis(thiocyanato-κN)cobalt(II)
 methanol solvate
;
_journal_coeditor_code           SI2239
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m189
_journal_paper_doi               10.1107/S1600536810002114
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Co (N C S)2 (C9 H10 N2 O)2], C H4 O'
_chemical_formula_moiety         'C20 H20 Co N6 O2 S2, C H4 O'
_chemical_formula_sum            'C21 H24 Co N6 O3 S2'
_chemical_formula_weight         531.53
_chemical_name_systematic
;Bis[(1-methyl-1H-benzimidazol-2-yl)methanol-
κ²N³,O]bis(thiocyanato-κN)cobalt(II)
methanol solvate
;
_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                95.579(3)
_cell_angle_beta                 103.388(3)
_cell_angle_gamma                95.179(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5008(13)
_cell_length_b                   10.3470(18)
_cell_length_c                   16.042(3)
_cell_measurement_reflns_used    4367
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.81
_cell_volume                     1197.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'publCIF (Westrip, 2010) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8542
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  0.9213
_exptl_absorpt_correction_T_min  0.7082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             550
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0643P)²+1.1088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                3288
_reflns_number_total             4146
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            si2239.cif
_cod_data_source_block           I
_cod_database_code               2225111
_cod_database_fobs_code          2225111
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
Co Co1 0.49422(6) 0.79547(4) 0.71477(3) 0.03196(15) Uani d . 1 . .
O O1 0.3407(3) 0.9076(2) 0.61010(13) 0.0388(5) Uani d . 1 . .
H H1 0.2553 0.9321 0.6326 0.058 Uiso d R 1 . .
O O2 0.2200(3) 0.7225(2) 0.74875(14) 0.0420(6) Uani d . 1 . .
H H2A 0.2062 0.6429 0.7575 0.063 Uiso d R 1 . .
O O3 0.0999(4) 0.4972(2) 0.79928(16) 0.0552(7) Uani d . 1 . .
H H3A 0.0496 0.5315 0.8370 0.083 Uiso d R 1 . .
N N1 0.3872(3) 0.6541(3) 0.61074(16) 0.0321(6) Uani d . 1 . .
N N2 0.2271(4) 0.5910(3) 0.47582(16) 0.0360(6) Uani d . 1 . .
N N3 0.4426(3) 0.9434(3) 0.80037(16) 0.0335(6) Uani d . 1 . .
N N4 0.3048(4) 1.0150(3) 0.90172(17) 0.0377(6) Uani d . 1 . .
N N5 0.7251(4) 0.8800(3) 0.68486(17) 0.0402(7) Uani d . 1 . .
N N6 0.6311(4) 0.6910(3) 0.80523(19) 0.0451(7) Uani d . 1 . .
C C1 0.2850(5) 0.8331(3) 0.5273(2) 0.0435(8) Uani d . 1 . .
H H1A 0.3651 0.8629 0.4901 0.052 Uiso calc R 1 . .
H H1B 0.1561 0.8449 0.4996 0.052 Uiso calc R 1 . .
C C2 0.2998(4) 0.6920(3) 0.53789(19) 0.0335(7) Uani d . 1 . .
C C3 0.3678(4) 0.5184(3) 0.59742(19) 0.0321(7) Uani d . 1 . .
C C4 0.4280(4) 0.4266(3) 0.6519(2) 0.0365(7) Uani d . 1 . .
H H4A 0.4974 0.4526 0.7096 0.044 Uiso calc R 1 . .
C C5 0.3834(5) 0.2958(3) 0.6193(2) 0.0447(8) Uani d . 1 . .
H H5A 0.4227 0.2310 0.6554 0.054 Uiso calc R 1 . .
C C6 0.2822(5) 0.2573(4) 0.5348(2) 0.0479(9) Uani d . 1 . .
H H6B 0.2539 0.1666 0.5148 0.057 Uiso calc R 1 . .
C C7 0.2218(5) 0.3459(4) 0.4795(2) 0.0430(8) Uani d . 1 . .
H H7A 0.1532 0.3190 0.4218 0.052 Uiso calc R 1 . .
C C8 0.2661(4) 0.4773(3) 0.51224(19) 0.0335(7) Uani d . 1 . .
C C9 0.1212(5) 0.5970(4) 0.3872(2) 0.0444(8) Uani d . 1 . .
H H9A 0.1124 0.6885 0.3776 0.067 Uiso calc R 1 . .
H H9B -0.0029 0.5510 0.3786 0.067 Uiso calc R 1 . .
H H9C 0.1837 0.5554 0.3462 0.067 Uiso calc R 1 . .
C C10 0.1814(5) 0.7973(3) 0.8195(2) 0.0412(8) Uani d . 1 . .
H H10A 0.1972 0.7475 0.8698 0.049 Uiso calc R 1 . .
H H10B 0.0525 0.8184 0.8045 0.049 Uiso calc R 1 . .
C C11 0.3106(4) 0.9185(3) 0.8402(2) 0.0348(7) Uani d . 1 . .
C C12 0.5277(4) 1.0679(3) 0.83793(19) 0.0332(7) Uani d . 1 . .
C C13 0.6722(4) 1.1464(4) 0.8213(2) 0.0427(8) Uani d . 1 . .
H H13A 0.7323 1.1183 0.7779 0.051 Uiso calc R 1 . .
C C14 0.7252(5) 1.2669(4) 0.8701(2) 0.0508(9) Uani d . 1 . .
H H14A 0.8219 1.3231 0.8589 0.061 Uiso calc R 1 . .
C C15 0.6418(5) 1.3092(4) 0.9354(2) 0.0506(9) Uani d . 1 . .
H H15A 0.6843 1.3923 0.9681 0.061 Uiso calc R 1 . .
C C16 0.4986(5) 1.2322(4) 0.9530(2) 0.0471(9) Uani d . 1 . .
H H16A 0.4411 1.2597 0.9975 0.056 Uiso calc R 1 . .
C C17 0.4430(4) 1.1128(3) 0.9026(2) 0.0373(7) Uani d . 1 . .
C C18 0.1719(5) 1.0184(4) 0.9551(2) 0.0528(10) Uani d . 1 . .
H H18A 0.0893 0.9362 0.9418 0.079 Uiso calc R 1 . .
H H18B 0.0995 1.0916 0.9433 0.079 Uiso calc R 1 . .
H H18C 0.2377 1.0295 1.0162 0.079 Uiso calc R 1 . .
C C19 0.8474(4) 0.9482(3) 0.6751(2) 0.0354(7) Uani d . 1 . .
C C20 0.7421(4) 0.6650(3) 0.8619(2) 0.0317(7) Uani d . 1 . .
C C21 0.2200(7) 0.4131(5) 0.8363(3) 0.0730(14) Uani d . 1 . .
H H21B 0.3474 0.4535 0.8455 0.109 Uiso calc R 1 . .
H H21A 0.2018 0.3309 0.7978 0.109 Uiso calc R 1 . .
H H21C 0.1958 0.3952 0.8918 0.109 Uiso calc R 1 . .
S S2 0.89902(12) 0.63097(9) 0.94306(5) 0.0424(2) Uani d . 1 . .
S S1 1.01807(12) 1.04930(9) 0.66347(6) 0.0445(2) Uani 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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 Co1 N5 . . 95.76(12) ?
N6 Co1 N1 . . 102.52(11) ?
N5 Co1 N1 . . 102.62(10) ?
N6 Co1 N3 . . 96.87(11) ?
N5 Co1 N3 . . 101.37(10) ?
N1 Co1 N3 . . 147.26(10) ?
N6 Co1 O1 . . 178.26(10) ?
N5 Co1 O1 . . 84.12(10) ?
N1 Co1 O1 . . 75.83(9) ?
N3 Co1 O1 . . 84.85(9) ?
N6 Co1 O2 . . 88.91(11) ?
N5 Co1 O2 . . 173.52(10) ?
N1 Co1 O2 . . 80.65(9) ?
N3 Co1 O2 . . 73.54(9) ?
O1 Co1 O2 . . 91.34(8) ?
C1 O1 Co1 . . 113.38(19) ?
C1 O1 H1 . . 116.7 ?
Co1 O1 H1 . . 100.9 ?
C10 O2 Co1 . . 114.71(19) ?
C10 O2 H2A . . 106.8 ?
Co1 O2 H2A . . 116.5 ?
C21 O3 H3A . . 109.5 ?
C2 N1 C3 . . 106.1(3) ?
C2 N1 Co1 . . 117.9(2) ?
C3 N1 Co1 . . 135.7(2) ?
C2 N2 C8 . . 106.9(3) ?
C2 N2 C9 . . 127.6(3) ?
C8 N2 C9 . . 125.5(3) ?
C11 N3 C12 . . 104.8(3) ?
C11 N3 Co1 . . 118.5(2) ?
C12 N3 Co1 . . 136.2(2) ?
C11 N4 C17 . . 107.4(3) ?
C11 N4 C18 . . 126.4(3) ?
C17 N4 C18 . . 126.2(3) ?
C19 N5 Co1 . . 167.6(3) ?
C20 N6 Co1 . . 160.2(3) ?
O1 C1 C2 . . 108.7(3) ?
O1 C1 H1A . . 110.0 ?
C2 C1 H1A . . 110.0 ?
O1 C1 H1B . . 110.0 ?
C2 C1 H1B . . 110.0 ?
H1A C1 H1B . . 108.3 ?
N1 C2 N2 . . 112.9(3) ?
N1 C2 C1 . . 122.2(3) ?
N2 C2 C1 . . 124.9(3) ?
C4 C3 N1 . . 131.5(3) ?
C4 C3 C8 . . 120.0(3) ?
N1 C3 C8 . . 108.5(3) ?
C5 C4 C3 . . 117.7(3) ?
C5 C4 H4A . . 121.2 ?
C3 C4 H4A . . 121.2 ?
C4 C5 C6 . . 121.3(3) ?
C4 C5 H5A . . 119.3 ?
C6 C5 H5A . . 119.3 ?
C7 C6 C5 . . 122.2(3) ?
C7 C6 H6B . . 118.9 ?
C5 C6 H6B . . 118.9 ?
C6 C7 C8 . . 116.5(3) ?
C6 C7 H7A . . 121.7 ?
C8 C7 H7A . . 121.7 ?
N2 C8 C7 . . 132.0(3) ?
N2 C8 C3 . . 105.7(3) ?
C7 C8 C3 . . 122.2(3) ?
N2 C9 H9A . . 109.5 ?
N2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
N2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O2 C10 C11 . . 107.8(3) ?
O2 C10 H10A . . 110.1 ?
C11 C10 H10A . . 110.1 ?
O2 C10 H10B . . 110.1 ?
C11 C10 H10B . . 110.1 ?
H10A C10 H10B . . 108.5 ?
N3 C11 N4 . . 113.3(3) ?
N3 C11 C10 . . 123.5(3) ?
N4 C11 C10 . . 123.2(3) ?
C13 C12 N3 . . 131.3(3) ?
C13 C12 C17 . . 119.5(3) ?
N3 C12 C17 . . 109.2(3) ?
C14 C13 C12 . . 117.4(3) ?
C14 C13 H13A . . 121.3 ?
C12 C13 H13A . . 121.3 ?
C13 C14 C15 . . 122.4(4) ?
C13 C14 H14A . . 118.8 ?
C15 C14 H14A . . 118.8 ?
C16 C15 C14 . . 121.0(3) ?
C16 C15 H15A . . 119.5 ?
C14 C15 H15A . . 119.5 ?
C15 C16 C17 . . 116.6(3) ?
C15 C16 H16A . . 121.7 ?
C17 C16 H16A . . 121.7 ?
N4 C17 C16 . . 131.6(3) ?
N4 C17 C12 . . 105.3(3) ?
C16 C17 C12 . . 123.2(3) ?
N4 C18 H18A . . 109.5 ?
N4 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N4 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N5 C19 S1 . . 177.8(3) ?
N6 C20 S2 . . 178.9(3) ?
O3 C21 H21B . . 109.5 ?
O3 C21 H21A . . 109.5 ?
H21B C21 H21A . . 109.5 ?
O3 C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
H21A C21 H21C . . 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
Co1 N6 . 2.035(3) y
Co1 N5 . 2.047(3) y
Co1 N1 . 2.065(3) y
Co1 N3 . 2.079(3) y
Co1 O1 . 2.284(2) y
Co1 O2 . 2.327(2) y
O1 C1 . 1.421(4) ?
O1 H1 . 0.8500 ?
O2 C10 . 1.411(4) ?
O2 H2A . 0.8500 ?
O3 C21 . 1.384(5) ?
O3 H3A . 0.8501 ?
N1 C2 . 1.315(4) ?
N1 C3 . 1.389(4) ?
N2 C2 . 1.351(4) ?
N2 C8 . 1.388(4) ?
N2 C9 . 1.470(4) ?
N3 C11 . 1.317(4) ?
N3 C12 . 1.397(4) ?
N4 C11 . 1.345(4) ?
N4 C17 . 1.378(4) ?
N4 C18 . 1.457(4) ?
N5 C19 . 1.155(4) ?
N6 C20 . 1.154(4) ?
C1 C2 . 1.498(5) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C3 C4 . 1.388(5) ?
C3 C8 . 1.405(4) ?
C4 C5 . 1.384(5) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.392(5) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.371(5) ?
C6 H6B . 0.9500 ?
C7 C8 . 1.390(5) ?
C7 H7A . 0.9500 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.474(5) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C12 C13 . 1.387(5) ?
C12 C17 . 1.401(4) ?
C13 C14 . 1.380(5) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.392(5) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.378(5) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.382(5) ?
C16 H16A . 0.9500 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 S1 . 1.636(4) ?
C20 S2 . 1.630(3) ?
C21 H21B . 0.9800 ?
C21 H21A . 0.9800 ?
C21 H21C . 0.9800 ?
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
O2 H2A O3 . 0.85 1.89 2.689(3) 155.2
O3 H3A S2 1_455 0.85 2.45 3.297(3) 178.8
O1 H1 S1 1_455 0.85 2.36 3.177(2) 161.7
