#------------------------------------------------------------------------------
#$Date: 2016-06-18 11:57:15 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183716 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/89/7118951.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_7118951
loop_
_publ_author_name
'Zhang, Hai-Rong'
'Huang, Ke-Bin'
'Chen, Zhen-Feng'
'Liu, Yan-Cheng'
'Liu, You-Nian'
'Meng, Ting'
'Qin, Qi-Pin'
'Zou, Bi-Qun'
'Liang, Hong'
_publ_section_title
;
 Cobalt(ii) 8-hydroxyquinoline complexes: structure, cytotoxicity and
 action mechanism
;
_journal_issue                   5
_journal_name_full               'Med. Chem. Commun.'
_journal_page_first              806
_journal_paper_doi               10.1039/C6MD00073H
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C28 H20 Co N6 O6, 2(C2 H2 O)'
_chemical_formula_sum            'C32 H32 Co N6 O8'
_chemical_formula_weight         687.57
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-24 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.880(4)
_cell_length_b                   13.110(3)
_cell_length_c                   14.440(3)
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.200
_cell_measurement_theta_min      2.483
_cell_volume                     3127.9(14)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16985
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.9140
_exptl_absorpt_correction_T_min  0.7749
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1428
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0943
_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)+(0.0893P)²+22.6178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2480
_refine_ls_wR_factor_ref         0.2596
_reflns_number_gt                2406
_reflns_number_total             3110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6md00073h2.cif
_cod_data_source_block           141017
_cod_depositor_comments
'Adding full bibliography for 7118950--7118952.cif.'
_cod_original_cell_volume        3127.9(11)
_cod_database_code               7118951
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O4-C15 = C15-C16
 1.45 with sigma of 0.02
 O4-C16
 2.5 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C3(H3), C11(H11), C7(H7), C5(H5), C1(H1), C2(H2), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 '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_calc_flag
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Co1 Co 0.2500 0.2500 0.5000 0.0473(4) Uani 1 d 2 S T P
C14 C 0.1117(3) 0.1328(4) 0.4304(4) 0.0434(12) Uani 1 d 1 . . .
N2 N 0.1337(3) 0.2332(3) 0.4414(4) 0.0480(12) Uani 1 d 1 . . .
C8 C -0.0303(4) 0.1776(6) 0.3612(5) 0.0646(18) Uani 1 d 1 . . .
H8 H -0.0850 0.1611 0.3350 0.078 Uiso 1 calc 1 R . .
C12 C 0.1637(4) -0.0437(5) 0.4586(5) 0.0605(17) Uani 1 d 1 . . .
H12 H 0.2053 -0.0915 0.4793 0.073 Uiso 1 calc 1 R . .
N3 N -0.0640(4) -0.0526(6) 0.3475(5) 0.079(2) Uani 1 d 1 . . .
C13 C 0.1794(3) 0.0639(5) 0.4654(5) 0.0486(14) Uani 1 d 1 . . .
O1 O 0.2530(2) 0.1038(3) 0.5029(3) 0.0579(11) Uani 1 d 1 . . .
N1 N 0.2547(3) 0.2490(4) 0.3651(4) 0.0537(13) Uani 1 d 1 . . .
C10 C 0.0169(4) -0.0072(6) 0.3849(5) 0.0643(19) Uani 1 d 1 . . .
C3 C 0.2613(6) 0.2471(8) 0.1749(7) 0.090(3) Uani 1 d 1 . . .
H3 H 0.2633 0.2470 0.1115 0.108 Uiso 1 calc 1 R . .
C11 C 0.0833(4) -0.0721(5) 0.4195(5) 0.0621(17) Uani 1 d 1 . . .
H11 H 0.0724 -0.1417 0.4161 0.075 Uiso 1 calc 1 R . .
C7 C -0.0053(4) 0.2789(6) 0.3735(6) 0.0667(19) Uani 1 d 1 . . .
H7 H -0.0440 0.3303 0.3548 0.080 Uiso 1 calc 1 R . .
C5 C 0.2218(4) 0.3254(6) 0.2990(5) 0.0620(17) Uani 1 d 1 . . .
H5 H 0.1965 0.3789 0.3178 0.074 Uiso 1 calc 1 R . .
C1 C 0.2908(4) 0.1719(6) 0.3360(6) 0.0668(19) Uani 1 d 1 . . .
H1 H 0.3139 0.1192 0.3810 0.080 Uiso 1 calc 1 R . .
C2 C 0.2951(6) 0.1676(7) 0.2405(8) 0.090(3) Uani 1 d 1 . . .
H2 H 0.3198 0.1130 0.2223 0.108 Uiso 1 calc 1 R . .
C4 C 0.2245(5) 0.3266(8) 0.2039(6) 0.081(2) Uani 1 d 1 . . .
O2 O -0.1235(4) -0.0004(5) 0.3049(6) 0.116(3) Uani 1 d 1 . . .
O3 O -0.0693(4) -0.1439(6) 0.3589(6) 0.125(3) Uani 1 d 1 . . .
C6 C 0.0783(4) 0.3055(4) 0.4140(5) 0.0593(17) Uani 1 d 1 . . .
H6 H 0.0938 0.3737 0.4211 0.071 Uiso 1 calc 1 R . .
C9 C 0.0293(4) 0.1003(5) 0.3895(5) 0.0551(16) Uani 1 d 1 . . .
O4 O 0.0803(8) 0.5395(8) 0.5111(10) 0.220(6) Uani 1 d 1 D . .
C15 C 0.0934(16) 0.6135(14) 0.4405(12) 0.32(2) Uani 1 d 1 D . .
H15A H 0.0647 0.6765 0.4401 0.379 Uiso 1 calc 1 R . .
H15B H 0.1506 0.6291 0.4622 0.379 Uiso 1 calc 1 R . .
C16 C 0.064(2) 0.570(3) 0.3402(15) 0.51(4) Uani 1 d 1 D . .
H4 H 0.204(4) 0.394(5) 0.162(4) 0.050(17) Uiso 1 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 Co1 N2 180.00(12) 7_556 .
N2 Co1 N1 89.3(2) . 7_556
N2 Co1 N1 90.7(2) . .
N2 Co1 N1 90.7(2) 7_556 7_556
N2 Co1 N1 89.3(2) 7_556 .
O1 Co1 N2 84.96(18) 7_556 7_556
O1 Co1 N2 95.04(18) 7_556 .
O1 Co1 N2 95.04(18) . 7_556
O1 Co1 N2 84.96(18) . .
O1 Co1 O1 180.0(3) . 7_556
O1 Co1 N1 90.2(2) 7_556 7_556
O1 Co1 N1 89.8(2) 7_556 .
O1 Co1 N1 89.8(2) . 7_556
O1 Co1 N1 90.2(2) . .
N1 Co1 N1 180.000(1) . 7_556
N2 C14 C13 113.5(5) . .
N2 C14 C9 122.8(5) . .
C9 C14 C13 123.7(6) . .
C14 N2 Co1 112.0(4) . .
C6 N2 Co1 127.5(4) . .
C6 N2 C14 120.6(5) . .
C7 C8 H8 120.7 . .
C7 C8 C9 118.6(5) . .
C9 C8 H8 120.7 . .
C13 C12 H12 122.0 . .
C11 C12 H12 122.0 . .
C11 C12 C13 116.1(6) . .
O2 N3 C10 120.5(7) . .
O3 N3 C10 117.9(8) . .
O3 N3 O2 121.6(7) . .
C12 C13 C14 118.5(5) . .
O1 C13 C14 117.8(5) . .
O1 C13 C12 123.6(6) . .
C13 O1 Co1 111.8(4) . .
C5 N1 Co1 121.2(5) . .
C1 N1 Co1 121.1(5) . .
C1 N1 C5 117.7(6) . .
C11 C10 N3 118.1(7) . .
C11 C10 C9 119.6(6) . .
C9 C10 N3 122.3(7) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C4 C3 C2 119.7(8) . .
C12 C11 C10 126.5(6) . .
C12 C11 H11 116.7 . .
C10 C11 H11 116.7 . .
C8 C7 H7 119.3 . .
C8 C7 C6 121.4(6) . .
C6 C7 H7 119.3 . .
N1 C5 H5 118.8 . .
N1 C5 C4 122.3(8) . .
C4 C5 H5 118.8 . .
N1 C1 H1 118.5 . .
N1 C1 C2 123.1(8) . .
C2 C1 H1 118.5 . .
C3 C2 C1 117.8(8) . .
C3 C2 H2 121.1 . .
C1 C2 H2 121.1 . .
C3 C4 C5 119.4(9) . .
C3 C4 H4 124(3) . .
C5 C4 H4 116(3) . .
N2 C6 C7 119.8(5) . .
N2 C6 H6 120.1 . .
C7 C6 H6 120.1 . .
C8 C9 C14 116.8(6) . .
C8 C9 C10 127.6(6) . .
C10 C9 C14 115.6(6) . .
O4 C15 H15A 109.8 . .
O4 C15 H15B 109.8 . .
H15A C15 H15B 108.2 . .
C16 C15 O4 109.5(17) . .
C16 C15 H15A 109.8 . .
C16 C15 H15B 109.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 N2 1.935(5) .
Co1 N2 1.935(5) 7_556
Co1 O1 1.917(4) .
Co1 O1 1.917(4) 7_556
Co1 N1 1.981(6) 7_556
Co1 N1 1.981(6) .
C14 N2 1.366(7) .
C14 C13 1.437(8) .
C14 C9 1.428(7) .
N2 C6 1.317(8) .
C8 H8 0.9300 .
C8 C7 1.391(10) .
C8 C9 1.412(10) .
C12 H12 0.9300 .
C12 C13 1.434(8) .
C12 C11 1.380(9) .
N3 C10 1.463(8) .
N3 O2 1.217(10) .
N3 O3 1.216(9) .
C13 O1 1.324(7) .
N1 C5 1.353(9) .
N1 C1 1.349(9) .
C10 C11 1.389(10) .
C10 C9 1.424(10) .
C3 H3 0.9300 .
C3 C2 1.383(13) .
C3 C4 1.380(13) .
C11 H11 0.9300 .
C7 H7 0.9300 .
C7 C6 1.425(9) .
C5 H5 0.9300 .
C5 C4 1.393(11) .
C1 H1 0.9300 .
C1 C2 1.411(11) .
C2 H2 0.9300 .
C4 H4 1.06(6) .
C6 H6 0.9300 .
O4 C15 1.489(16) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.456(19) .
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
_geom_torsion_site_symmetry_1
Co1 N2 C6 C7 -178.9(5) .
Co1 N1 C5 C4 179.8(5) .
Co1 N1 C1 C2 179.5(6) .
C14 N2 C6 C7 0.7(10) .
C14 C13 O1 Co1 -0.3(7) .
N2 Co1 N2 C14 -174(100) 7_556
N2 Co1 N2 C6 6(53) 7_556
N2 Co1 O1 C13 0.5(4) .
N2 Co1 O1 C13 -179.5(4) 7_556
N2 Co1 N1 C5 66.9(4) .
N2 Co1 N1 C5 -113.1(4) 7_556
N2 Co1 N1 C1 67.0(5) 7_556
N2 Co1 N1 C1 -113.0(5) .
N2 C14 C13 C12 179.4(6) .
N2 C14 C13 O1 -0.2(8) .
N2 C14 C9 C8 -0.7(9) .
N2 C14 C9 C10 -178.9(6) .
C8 C7 C6 N2 -0.5(12) .
C12 C13 O1 Co1 -179.8(5) .
N3 C10 C11 C12 -179.1(6) .
N3 C10 C9 C14 178.3(6) .
N3 C10 C9 C8 0.4(11) .
C13 C14 N2 Co1 0.6(6) .
C13 C14 N2 C6 -179.1(6) .
C13 C14 C9 C8 178.1(6) .
C13 C14 C9 C10 0.0(9) .
C13 C12 C11 C10 1.3(11) .
O1 Co1 N2 C14 -0.6(4) .
O1 Co1 N2 C14 179.4(4) 7_556
O1 Co1 N2 C6 179.0(6) .
O1 Co1 N2 C6 -1.0(6) 7_556
O1 Co1 O1 C13 26(3) 7_556
O1 Co1 N1 C5 151.9(4) .
O1 Co1 N1 C5 -28.1(4) 7_556
O1 Co1 N1 C1 -28.0(5) .
O1 Co1 N1 C1 152.0(5) 7_556
N1 Co1 N2 C14 -90.5(4) 7_556
N1 Co1 N2 C14 89.5(4) .
N1 Co1 N2 C6 -90.8(6) .
N1 Co1 N2 C6 89.2(6) 7_556
N1 Co1 O1 C13 -90.2(4) .
N1 Co1 O1 C13 89.8(4) 7_556
N1 Co1 N1 C5 5(100) 7_556
N1 Co1 N1 C1 -175(100) 7_556
N1 C5 C4 C3 0.5(11) .
N1 C1 C2 C3 0.8(12) .
C11 C12 C13 C14 -1.0(9) .
C11 C12 C13 O1 178.6(6) .
C11 C10 C9 C14 0.2(10) .
C11 C10 C9 C8 -177.7(7) .
C7 C8 C9 C14 0.9(10) .
C7 C8 C9 C10 178.8(7) .
C5 N1 C1 C2 -0.4(10) .
C1 N1 C5 C4 -0.3(9) .
C2 C3 C4 C5 -0.1(12) .
C4 C3 C2 C1 -0.5(13) .
O2 N3 C10 C11 -170.7(8) .
O2 N3 C10 C9 11.2(11) .
O3 N3 C10 C11 8.1(11) .
O3 N3 C10 C9 -170.0(8) .
C9 C14 N2 Co1 179.6(5) .
C9 C14 N2 C6 -0.1(9) .
C9 C14 C13 C12 0.4(9) .
C9 C14 C13 O1 -179.2(6) .
C9 C8 C7 C6 -0.3(11) .
C9 C10 C11 C12 -0.9(11) .
