#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:41:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179257 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/77/4317749.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_4317749
loop_
_publ_author_name
'Brian S. Hammes'
'Matthew T. Kieber-Emmons'
'Roger Sommer'
'Arnold L. Rheingold'
_publ_section_title
;
 Modulating the Reduction Potential of Mononuclear Cobalt(II) Complexes
 via Selective Deprotonation of Tris[(2-benzimidazolyl)methyl]amine
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1351
_journal_page_last               1353
_journal_paper_doi               10.1021/ic0155885
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C31 H34 Co N10 O2 S'
_chemical_formula_weight         669.67
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.6750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3530(9)
_cell_length_b                   11.0645(6)
_cell_length_c                   19.1319(10)
_cell_measurement_reflns_used    7580
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.225
_cell_measurement_theta_min      4.769
_cell_volume                     3129.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  '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  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15545
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  0.8789
_exptl_absorpt_correction_T_min  0.8261
_exptl_absorpt_correction_type   'Empirical from SADABS'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         7241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0464P)²+2.0199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                5660
_reflns_number_total             7241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0155885_1.cif
_cod_data_source_block           bsh04
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4317749
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Co1 Co 0.23326(2) 0.35436(3) 0.455934(16) 0.01812(9) Uani 1 1 d . . .
N1 N 0.17032(14) 0.41350(17) 0.33452(10) 0.0199(4) Uani 1 1 d . . .
N2 N 0.34218(14) 0.40598(17) 0.42214(10) 0.0202(4) Uani 1 1 d . . .
N3 N 0.40037(15) 0.49212(18) 0.33934(11) 0.0213(4) Uani 1 1 d . . .
N4 N 0.14376(14) 0.49012(18) 0.46223(10) 0.0211(4) Uani 1 1 d . . .
N5 N 0.02449(16) 0.60409(19) 0.41032(12) 0.0245(5) Uani 1 1 d . . .
N6 N 0.18614(14) 0.19929(17) 0.40559(10) 0.0199(4) Uani 1 1 d . . .
N7 N 0.14997(14) 0.08430(18) 0.30271(10) 0.0226(4) Uani 1 1 d . . .
N8 N 0.28892(16) 0.30979(19) 0.56087(11) 0.0264(5) Uani 1 1 d . . .
C1 C 0.23218(17) 0.5074(2) 0.32178(13) 0.0225(5) Uani 1 1 d . . .
H1A H 0.2179 0.5863 0.3405 0.027 Uiso 1 1 calc R . .
H1B H 0.2262 0.5156 0.2692 0.027 Uiso 1 1 calc R . .
C2 C 0.32555(17) 0.4691(2) 0.36071(12) 0.0207(5) Uani 1 1 d . . .
C3 C 0.43502(17) 0.3848(2) 0.44141(12) 0.0197(5) Uani 1 1 d . . .
C4 C 0.47209(17) 0.4383(2) 0.38945(12) 0.0215(5) Uani 1 1 d . . .
C5 C 0.56336(18) 0.4289(2) 0.39334(14) 0.0262(5) Uani 1 1 d . . .
H5A H 0.5881 0.4647 0.3578 0.031 Uiso 1 1 calc R . .
C6 C 0.61682(18) 0.3647(2) 0.45173(14) 0.0292(6) Uani 1 1 d . . .
H6A H 0.6797 0.3564 0.4562 0.035 Uiso 1 1 calc R . .
C7 C 0.58040(19) 0.3121(2) 0.50400(14) 0.0283(6) Uani 1 1 d . . .
H7A H 0.6191 0.2689 0.5432 0.034 Uiso 1 1 calc R . .
C8 C 0.48962(18) 0.3212(2) 0.49999(13) 0.0236(5) Uani 1 1 d . . .
H8A H 0.4652 0.2856 0.5357 0.028 Uiso 1 1 calc R . .
C9 C 0.07977(17) 0.4591(2) 0.33062(12) 0.0229(5) Uani 1 1 d . . .
H9A H 0.0359 0.3915 0.3218 0.027 Uiso 1 1 calc R . .
H9B H 0.0606 0.5175 0.2902 0.027 Uiso 1 1 calc R . .
C10 C 0.08238(17) 0.5193(2) 0.40087(13) 0.0212(5) Uani 1 1 d . . .
C11 C 0.12304(17) 0.5631(2) 0.51546(13) 0.0232(5) Uani 1 1 d . . .
C12 C 0.04844(18) 0.6349(2) 0.48315(14) 0.0255(5) Uani 1 1 d . . .
C13 C 0.0128(2) 0.7191(2) 0.52194(16) 0.0330(6) Uani 1 1 d . . .
H13A H -0.0383 0.7672 0.4992 0.040 Uiso 1 1 calc R . .
C14 C 0.0553(2) 0.7293(3) 0.59463(16) 0.0381(7) Uani 1 1 d . . .
H14A H 0.0337 0.7865 0.6230 0.046 Uiso 1 1 calc R . .
C15 C 0.1297(2) 0.6573(3) 0.62791(15) 0.0364(7) Uani 1 1 d . . .
H15A H 0.1570 0.6668 0.6784 0.044 Uiso 1 1 calc R . .
C16 C 0.16514(19) 0.5726(2) 0.58991(13) 0.0293(6) Uani 1 1 d . . .
H16A H 0.2154 0.5235 0.6131 0.035 Uiso 1 1 calc R . .
C17 C 0.16911(18) 0.3057(2) 0.28895(12) 0.0223(5) Uani 1 1 d . . .
H17A H 0.2245 0.3038 0.2718 0.027 Uiso 1 1 calc R . .
H17B H 0.1161 0.3090 0.2459 0.027 Uiso 1 1 calc R . .
C18 C 0.16444(16) 0.1937(2) 0.33215(12) 0.0188(5) Uani 1 1 d . . .
C19 C 0.18767(17) 0.0788(2) 0.42643(13) 0.0215(5) Uani 1 1 d . . .
C20 C 0.16647(17) 0.0082(2) 0.36282(13) 0.0217(5) Uani 1 1 d . . .
C21 C 0.16904(18) -0.1183(2) 0.36642(14) 0.0269(6) Uani 1 1 d . . .
H21A H 0.1565 -0.1664 0.3237 0.032 Uiso 1 1 calc R . .
C22 C 0.19045(18) -0.1696(2) 0.43419(15) 0.0280(6) Uani 1 1 d . . .
H22A H 0.1936 -0.2552 0.4382 0.034 Uiso 1 1 calc R . .
C23 C 0.2078(2) -0.1000(2) 0.49759(15) 0.0309(6) Uani 1 1 d . . .
H23A H 0.2203 -0.1394 0.5434 0.037 Uiso 1 1 calc R . .
C24 C 0.20722(19) 0.0251(2) 0.49490(13) 0.0274(6) Uani 1 1 d . . .
H24A H 0.2196 0.0724 0.5379 0.033 Uiso 1 1 calc R . .
C25 C 0.34051(18) 0.2925(2) 0.61637(13) 0.0239(5) Uani 1 1 d . . .
S2 S 0.41404(5) 0.26915(7) 0.69478(4) 0.03714(19) Uani 1 1 d . . .
C1S C 0.4525(3) 0.1754(3) 0.31154(19) 0.0533(9) Uani 1 1 d . . .
H1SA H 0.5006 0.2089 0.2954 0.064 Uiso 1 1 calc R . .
C2S C 0.4079(3) 0.0413(4) 0.3933(2) 0.0777(13) Uani 1 1 d . . .
H2SA H 0.3488 0.0753 0.3685 0.117 Uiso 1 1 calc R . .
H2SB H 0.4232 0.0627 0.4449 0.117 Uiso 1 1 calc R . .
H2SC H 0.4058 -0.0469 0.3883 0.117 Uiso 1 1 calc R . .
C3S C 0.5674(3) 0.0523(4) 0.3893(3) 0.0905(17) Uani 1 1 d . . .
H3SA H 0.6043 0.0933 0.3620 0.136 Uiso 1 1 calc R . .
H3SB H 0.5720 -0.0354 0.3838 0.136 Uiso 1 1 calc R . .
H3SC H 0.5891 0.0739 0.4407 0.136 Uiso 1 1 calc R . .
C4S C 0.8307(2) 0.7779(3) 0.29757(16) 0.0361(7) Uani 1 1 d . . .
H4SA H 0.7679 0.7596 0.2856 0.043 Uiso 1 1 calc R . .
C5S C 0.9480(3) 0.9288(4) 0.3264(3) 0.0715(13) Uani 1 1 d . . .
H5SA H 0.9860 0.8568 0.3293 0.107 Uiso 1 1 calc R . .
H5SB H 0.9642 0.9708 0.3732 0.107 Uiso 1 1 calc R . .
H5SC H 0.9576 0.9830 0.2886 0.107 Uiso 1 1 calc R . .
C6S C 0.7863(2) 0.9878(3) 0.30180(19) 0.0479(8) Uani 1 1 d . . .
H6SA H 0.7258 0.9517 0.2900 0.072 Uiso 1 1 calc R . .
H6SB H 0.7904 1.0437 0.2630 0.072 Uiso 1 1 calc R . .
H6SC H 0.7973 1.0321 0.3478 0.072 Uiso 1 1 calc R . .
H3A H 0.402(2) 0.526(3) 0.3026(18) 0.049(10) Uiso 1 1 d . . .
H5B H -0.016(2) 0.625(2) 0.3785(15) 0.024(8) Uiso 1 1 d . . .
N1S N 0.47491(18) 0.0888(2) 0.36187(14) 0.0401(6) Uani 1 1 d . . .
N2S N 0.85365(17) 0.8930(2) 0.30863(14) 0.0374(6) Uani 1 1 d . . .
O1S O 0.37877(18) 0.21535(19) 0.28459(12) 0.0517(6) Uani 1 1 d . . .
O2S O 0.88312(16) 0.69226(19) 0.30130(13) 0.0506(6) Uani 1 1 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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 Co1 N8 105.64(8) . . ?
N6 Co1 N2 108.00(8) . . ?
N8 Co1 N2 102.80(9) . . ?
N6 Co1 N4 119.48(8) . . ?
N8 Co1 N4 103.27(8) . . ?
N2 Co1 N4 115.65(8) . . ?
N6 Co1 N1 76.42(7) . . ?
N8 Co1 N1 177.93(8) . . ?
N2 Co1 N1 76.20(7) . . ?
N4 Co1 N1 75.69(7) . . ?
C9 N1 C1 113.29(19) . . ?
C9 N1 C17 112.89(19) . . ?
C1 N1 C17 112.26(19) . . ?
C9 N1 Co1 106.10(13) . . ?
C1 N1 Co1 104.38(13) . . ?
C17 N1 Co1 107.14(13) . . ?
C2 N2 C3 105.1(2) . . ?
C2 N2 Co1 116.78(17) . . ?
C3 N2 Co1 137.78(16) . . ?
C2 N3 C4 107.0(2) . . ?
C10 N4 C11 104.8(2) . . ?
C10 N4 Co1 116.71(16) . . ?
C11 N4 Co1 138.41(16) . . ?
C10 N5 C12 107.6(2) . . ?
C18 N6 C19 103.55(18) . . ?
C18 N6 Co1 119.52(16) . . ?
C19 N6 Co1 135.01(15) . . ?
C18 N7 C20 103.23(19) . . ?
C25 N8 Co1 162.6(2) . . ?
N1 C1 C2 107.10(18) . . ?
N2 C2 N3 113.1(2) . . ?
N2 C2 C1 121.4(2) . . ?
N3 C2 C1 125.6(2) . . ?
N2 C3 C8 130.4(2) . . ?
N2 C3 C4 108.9(2) . . ?
C8 C3 C4 120.7(2) . . ?
N3 C4 C5 132.2(2) . . ?
N3 C4 C3 105.9(2) . . ?
C5 C4 C3 121.9(2) . . ?
C4 C5 C6 116.7(2) . . ?
C5 C6 C7 121.6(3) . . ?
C8 C7 C6 121.5(2) . . ?
C7 C8 C3 117.4(2) . . ?
N1 C9 C10 108.34(19) . . ?
N4 C10 N5 112.9(2) . . ?
N4 C10 C9 121.8(2) . . ?
N5 C10 C9 125.3(2) . . ?
C12 C11 C16 120.4(2) . . ?
C12 C11 N4 109.1(2) . . ?
C16 C11 N4 130.5(2) . . ?
N5 C12 C13 131.7(3) . . ?
N5 C12 C11 105.6(2) . . ?
C13 C12 C11 122.6(2) . . ?
C14 C13 C12 116.6(3) . . ?
C13 C14 C15 121.5(3) . . ?
C16 C15 C14 122.4(3) . . ?
C15 C16 C11 116.5(3) . . ?
N1 C17 C18 109.68(18) . . ?
N7 C18 N6 116.6(2) . . ?
N7 C18 C17 123.1(2) . . ?
N6 C18 C17 119.9(2) . . ?
N6 C19 C24 131.3(2) . . ?
N6 C19 C20 107.6(2) . . ?
C24 C19 C20 121.1(2) . . ?
N7 C20 C21 129.9(2) . . ?
N7 C20 C19 109.0(2) . . ?
C21 C20 C19 121.0(2) . . ?
C22 C21 C20 117.2(2) . . ?
C21 C22 C23 122.1(2) . . ?
C24 C23 C22 121.3(2) . . ?
C23 C24 C19 117.3(2) . . ?
N8 C25 S2 179.5(3) . . ?
O1S C1S N1S 127.3(4) . . ?
O2S C4S N2S 126.1(3) . . ?
C1S N1S C2S 119.6(3) . . ?
C1S N1S C3S 120.2(4) . . ?
C2S N1S C3S 119.9(4) . . ?
C4S N2S C5S 120.4(3) . . ?
C4S N2S C6S 121.8(3) . . ?
C5S N2S C6S 117.7(3) . . ?
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
Co1 N6 2.0046(19) . ?
Co1 N8 2.019(2) . ?
Co1 N2 2.031(2) . ?
Co1 N4 2.061(2) . ?
Co1 N1 2.3547(19) . ?
N1 C9 1.462(3) . ?
N1 C1 1.472(3) . ?
N1 C17 1.475(3) . ?
N2 C2 1.331(3) . ?
N2 C3 1.392(3) . ?
N3 C2 1.344(3) . ?
N3 C4 1.384(3) . ?
N4 C10 1.331(3) . ?
N4 C11 1.402(3) . ?
N5 C10 1.338(3) . ?
N5 C12 1.384(3) . ?
N6 C18 1.355(3) . ?
N6 C19 1.390(3) . ?
N7 C18 1.328(3) . ?
N7 C20 1.392(3) . ?
N8 C25 1.156(3) . ?
C1 C2 1.487(3) . ?
C3 C8 1.395(3) . ?
C3 C4 1.403(3) . ?
C4 C5 1.387(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.398(4) . ?
C7 C8 1.379(4) . ?
C9 C10 1.491(3) . ?
C11 C12 1.393(4) . ?
C11 C16 1.400(3) . ?
C12 C13 1.392(4) . ?
C13 C14 1.372(4) . ?
C14 C15 1.397(4) . ?
C15 C16 1.384(4) . ?
C17 C18 1.502(3) . ?
C19 C24 1.395(3) . ?
C19 C20 1.408(3) . ?
C20 C21 1.401(3) . ?
C21 C22 1.372(4) . ?
C22 C23 1.400(4) . ?
C23 C24 1.385(3) . ?
C25 S2 1.636(3) . ?
C1S O1S 1.195(4) . ?
C1S N1S 1.336(4) . ?
C2S N1S 1.425(5) . ?
C3S N1S 1.432(5) . ?
C4S O2S 1.233(3) . ?
C4S N2S 1.323(4) . ?
C5S N2S 1.451(4) . ?
C6S N2S 1.454(4) . ?
