#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/39/2223942.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_2223942
loop_
_publ_author_name
'Wang, Hao'
'Song, Wen-Dong'
'Li, Shi-Jie'
'Miao, Dong-Liang'
'Liu, Jin'
_publ_section_title
;Tetraaquabis(1H-benzimidazole-5,6-dicarboxylato-κN³)cobalt(II)
 dimethylformamide disolvate dihydrate
;
_journal_coeditor_code           NG2669
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1423
_journal_paper_doi               10.1107/S1600536809043177
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'[Co (C9 H5 N2 O4)2 (H2 O)4], 2C3 H7 N O, 2H2 O'
_chemical_formula_moiety         'C18 H18 Co N4 O12, 2(C3 H7 N O), 2(H2 O)'
_chemical_formula_sum            'C24 H36 Co N6 O16'
_chemical_formula_weight         723.52
_chemical_name_systematic
;
Tetraaquabis(1H-benzimidazole-5,6-dicarboxylato-
κN³)cobalt(II) dimethylformamide 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                100.82(3)
_cell_angle_beta                 102.98(3)
_cell_angle_gamma                114.11(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5612(17)
_cell_length_b                   9.1475(18)
_cell_length_c                   11.642(2)
_cell_measurement_reflns_used    3420
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.27
_cell_volume                     769.9(4)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6161
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         3.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_correction_T_min  0.8306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             377
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.437
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0376
_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)+(0.0795P)²+1.1940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                2594
_reflns_number_total             2751
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2669.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_cell_volume        769.9(3)
_cod_database_code               2223942
_cod_database_fobs_code          2223942
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
C C1 0.1417(4) 0.8422(3) 0.1200(2) 0.0279(6) Uani d . 1 . .
C C2 0.2484(3) 0.8904(3) 0.2467(2) 0.0247(5) Uani d . 1 . .
C C3 0.1906(3) 0.7887(3) 0.3191(2) 0.0269(5) Uani d . 1 . .
H H3 0.2595 0.8201 0.4020 0.032 Uiso calc R 1 . .
C C4 0.0277(3) 0.6389(3) 0.2654(2) 0.0248(5) Uani d . 1 . .
C C5 -0.0742(3) 0.5940(3) 0.1405(2) 0.0272(6) Uani d . 1 . .
C C6 -0.0194(4) 0.6932(4) 0.0667(2) 0.0309(6) Uani d . 1 . .
H H6 -0.0888 0.6606 -0.0163 0.037 Uiso calc R 1 . .
C C7 0.1921(4) 0.9449(4) 0.0363(3) 0.0324(6) Uani d . 1 . .
C C8 0.4297(3) 1.0478(3) 0.3103(2) 0.0263(5) Uani d . 1 . .
C C9 -0.2117(4) 0.4034(3) 0.2225(3) 0.0310(6) Uani d . 1 . .
H H9 -0.2984 0.3064 0.2299 0.037 Uiso calc R 1 . .
C C10 0.6732(4) 0.7964(4) 0.1713(3) 0.0344(6) Uani d . 1 . .
H H10 0.7801 0.8972 0.1955 0.041 Uiso calc R 1 . .
N N3 0.6382(3) 0.7242(3) 0.2550(2) 0.0340(5) Uani d . 1 . .
Co Co1 0.0000 0.5000 0.5000 0.02238(18) Uani d S 1 . .
N N1 -0.2262(3) 0.4426(3) 0.1168(2) 0.0315(5) Uani d . 1 . .
H H1 -0.3137 0.3846 0.0473 0.038 Uiso calc R 1 . .
N N2 -0.0630(3) 0.5150(3) 0.3148(2) 0.0282(5) Uani d . 1 . .
C C12 0.4674(5) 0.5710(5) 0.2251(4) 0.0552(9) Uani d . 1 . .
H H3A 0.3742 0.6008 0.2330 0.083 Uiso calc R 1 . .
H H3B 0.4829 0.5094 0.2812 0.083 Uiso calc R 1 . .
H H3C 0.4330 0.5021 0.1414 0.083 Uiso calc R 1 . .
C C11 0.7568(6) 0.8059(5) 0.3848(3) 0.0547(9) Uani d . 1 . .
H H4A 0.8640 0.9036 0.3911 0.082 Uiso calc R 1 . .
H H4B 0.7907 0.7283 0.4145 0.082 Uiso calc R 1 . .
H H4C 0.6937 0.8393 0.4340 0.082 Uiso calc R 1 . .
O O1 0.1079(3) 0.8972(3) -0.0726(2) 0.0582(7) Uani d . 1 . .
O O2 0.3337(4) 1.0933(3) 0.0904(2) 0.0635(8) Uani d D 1 . .
O O3 0.4308(3) 1.1767(3) 0.3708(2) 0.0458(6) Uani d . 1 . .
O O4 0.5660(3) 1.0359(3) 0.3035(3) 0.0524(6) Uani d . 1 . .
O O5 0.5725(3) 0.7391(3) 0.06005(19) 0.0457(6) Uani d . 1 . .
O O1W 0.0884(2) 0.7574(2) 0.57397(17) 0.0300(4) Uani d D 1 . .
H H2W 0.0296 0.7784 0.6176 0.045 Uiso d RD 1 . .
H H1W 0.2007 0.8133 0.6126 0.045 Uiso d RD 1 . .
O O2W 0.2619(3) 0.5455(2) 0.50191(19) 0.0360(5) Uani d D 1 . .
H H4W 0.2576 0.4881 0.4347 0.054 Uiso d RD 1 . .
H H3W 0.3630 0.6321 0.5381 0.054 Uiso d RD 1 . .
O O3W 0.1590(3) 0.2539(3) 0.3083(2) 0.0498(6) Uani d D 1 . .
H H5W 0.2452 0.2312 0.3275 0.075 Uiso d RD 1 . .
H H6W 0.0905 0.2004 0.2343 0.075 Uiso d RD 1 . .
H H2 0.367(6) 1.146(5) 0.041(3) 0.075 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'
Co Co 0.3494 0.9721 '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
C6 C1 C2 . . 120.8(2) ?
C6 C1 C7 . . 115.4(2) ?
C2 C1 C7 . . 123.8(2) ?
C3 C2 C1 . . 120.3(2) ?
C3 C2 C8 . . 115.8(2) ?
C1 C2 C8 . . 123.9(2) ?
C2 C3 C4 . . 118.9(2) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C3 C4 N2 . . 131.3(2) ?
C3 C4 C5 . . 119.7(2) ?
N2 C4 C5 . . 108.9(2) ?
C6 C5 N1 . . 132.1(2) ?
C6 C5 C4 . . 122.4(2) ?
N1 C5 C4 . . 105.5(2) ?
C1 C6 C5 . . 117.9(2) ?
C1 C6 H6 . . 121.0 ?
C5 C6 H6 . . 121.0 ?
O1 C7 O2 . . 121.9(3) ?
O1 C7 C1 . . 123.1(3) ?
O2 C7 C1 . . 115.0(2) ?
O4 C8 O3 . . 125.2(3) ?
O4 C8 C2 . . 117.0(2) ?
O3 C8 C2 . . 117.7(2) ?
N2 C9 N1 . . 113.6(2) ?
N2 C9 H9 . . 123.2 ?
N1 C9 H9 . . 123.2 ?
O5 C10 N3 . . 124.3(3) ?
O5 C10 H10 . . 117.8 ?
N3 C10 H10 . . 117.8 ?
C10 N3 C12 . . 120.6(3) ?
C10 N3 C11 . . 120.7(3) ?
C12 N3 C11 . . 118.2(3) ?
O1W Co1 O1W . 2_566 180.0 ?
O1W Co1 O2W . 2_566 88.64(8) ?
O1W Co1 O2W 2_566 2_566 91.36(8) ?
O1W Co1 O2W . . 91.36(8) ?
O1W Co1 O2W 2_566 . 88.64(8) ?
O2W Co1 O2W 2_566 . 180.0 ?
O1W Co1 N2 . . 90.82(9) ?
O1W Co1 N2 2_566 . 89.18(9) ?
O2W Co1 N2 2_566 . 90.29(9) ?
O2W Co1 N2 . . 89.71(9) ?
O1W Co1 N2 . 2_566 89.18(9) ?
O1W Co1 N2 2_566 2_566 90.82(9) ?
O2W Co1 N2 2_566 2_566 89.71(9) ?
O2W Co1 N2 . 2_566 90.29(9) ?
N2 Co1 N2 . 2_566 179.9990(10) ?
C9 N1 C5 . . 107.1(2) ?
C9 N1 H1 . . 126.5 ?
C5 N1 H1 . . 126.5 ?
C9 N2 C4 . . 104.9(2) ?
C9 N2 Co1 . . 124.00(18) ?
C4 N2 Co1 . . 130.98(18) ?
N3 C12 H3A . . 109.5 ?
N3 C12 H3B . . 109.5 ?
H3A C12 H3B . . 109.5 ?
N3 C12 H3C . . 109.5 ?
H3A C12 H3C . . 109.5 ?
H3B C12 H3C . . 109.5 ?
N3 C11 H4A . . 109.5 ?
N3 C11 H4B . . 109.5 ?
H4A C11 H4B . . 109.5 ?
N3 C11 H4C . . 109.5 ?
H4A C11 H4C . . 109.5 ?
H4B C11 H4C . . 109.5 ?
C7 O2 H2 . . 114(3) ?
Co1 O1W H2W . . 113.1 ?
Co1 O1W H1W . . 113.3 ?
H2W O1W H1W . . 110.9 ?
Co1 O2W H4W . . 110.8 ?
Co1 O2W H3W . . 130.9 ?
H4W O2W H3W . . 112.2 ?
H5W O3W H6W . . 112.2 ?
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
C1 C6 . 1.381(4) ?
C1 C2 . 1.424(4) ?
C1 C7 . 1.489(4) ?
C2 C3 . 1.387(4) ?
C2 C8 . 1.513(4) ?
C3 C4 . 1.393(4) ?
C3 H3 . 0.9300 ?
C4 N2 . 1.395(3) ?
C4 C5 . 1.398(4) ?
C5 C6 . 1.382(4) ?
C5 N1 . 1.382(3) ?
C6 H6 . 0.9300 ?
C7 O1 . 1.201(4) ?
C7 O2 . 1.304(4) ?
C8 O4 . 1.234(3) ?
C8 O3 . 1.250(3) ?
C9 N2 . 1.315(4) ?
C9 N1 . 1.338(4) ?
C9 H9 . 0.9300 ?
C10 O5 . 1.253(3) ?
C10 N3 . 1.299(4) ?
C10 H10 . 0.9300 ?
N3 C12 . 1.462(4) ?
N3 C11 . 1.463(4) ?
Co1 O1W . 2.086(2) ?
Co1 O1W 2_566 2.086(2) ?
Co1 O2W 2_566 2.1007(19) ?
Co1 O2W . 2.1007(19) ?
Co1 N2 . 2.146(2) ?
Co1 N2 2_566 2.146(2) ?
N1 H1 . 0.8600 ?
C12 H3A . 0.9600 ?
C12 H3B . 0.9600 ?
C12 H3C . 0.9600 ?
C11 H4A . 0.9600 ?
C11 H4B . 0.9600 ?
C11 H4C . 0.9600 ?
O2 H2 . 0.839(10) ?
O1W H2W . 0.8400 ?
O1W H1W . 0.8400 ?
O2W H4W . 0.8399 ?
O2W H3W . 0.8399 ?
O3W H5W . 0.8400 ?
O3W H6W . 0.8399 ?
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 H2 O5 2_675 0.839(10) 1.750(11) 2.588(3) 177(5)
O3W H6W O1 2_565 0.84 1.98 2.800(3) 165.1
O3W H5W O3 1_545 0.84 1.85 2.686(3) 178.5
O2W H3W O3 2_676 0.84 1.80 2.636(3) 173.5
O2W H4W O3W . 0.84 2.06 2.811(3) 148.3
O1W H1W O4 2_676 0.84 1.79 2.624(3) 170.0
O1W H2W O3W 2_566 0.84 1.94 2.749(3) 160.7
N1 H1 O5 2_565 0.86 1.98 2.782(3) 154.3
N1 H1 O5 2_565 0.86 1.98 2.782(3) 154.3
