#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:37:24 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179589 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/54/4505475.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_4505475
loop_
_publ_author_name
'Chen, Zhi'
'Gao, Dong-Liang'
'Diao, Chun-Hua'
'Liu, Yue'
'Ren, Jia'
'Chen, Ji'
'Zhao, Bin'
'Shi, Wei'
'Cheng, Peng'
_publ_section_title
;
 Syntheses, Structures Tuned by 4,4′-Bipyridine and Magnetic
 Properties of a Series of Transition Metal Compounds
 Containingo-Carboxylphenoxyacetate Acid
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1201
_journal_paper_doi               10.1021/cg201197k
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C28 H28 Co2 N2 O14'
_chemical_formula_weight         734.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 107.709(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7351(10)
_cell_length_b                   23.513(3)
_cell_length_c                   6.5060(8)
_cell_measurement_reflns_used    11564
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      3.28
_cell_volume                     1418.7(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  SCX-MINI
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11123
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    1.248
_exptl_absorpt_correction_T_max  0.8853
_exptl_absorpt_correction_T_min  0.7058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0348P)²+0.1765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                1978
_reflns_number_total             2493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201197k_si_002.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4505475
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Co1 Co 0.51808(5) 0.10826(2) -0.06693(7) 0.02621(16) Uani 1 1 d .
O1 O 0.5926(3) 0.18520(10) 0.1064(4) 0.0373(6) Uani 1 1 d D
H1A H 0.569(4) 0.2156(9) 0.034(4) 0.045 Uiso 1 1 d D
H1B H 0.568(4) 0.1868(13) 0.221(3) 0.045 Uiso 1 1 d D
O2 O 0.4696(3) 0.03747(10) -0.2713(4) 0.0426(7) Uani 1 1 d D
H2A H 0.500(4) 0.0037(7) -0.246(5) 0.051 Uiso 1 1 d D
H2B H 0.415(4) 0.0415(13) -0.400(3) 0.051 Uiso 1 1 d D
O3 O 0.4176(2) 0.07811(10) 0.1356(4) 0.0325(6) Uani 1 1 d .
O4 O 0.2770(3) 0.06835(11) 0.3402(4) 0.0393(7) Uani 1 1 d .
O5 O 0.3139(2) 0.15164(10) -0.2173(4) 0.0310(6) Uani 1 1 d .
O6 O 0.5609(3) 0.14873(10) -0.3164(4) 0.0355(6) Uani 1 1 d .
O7 O 0.4810(3) 0.21115(10) -0.5816(4) 0.0417(7) Uani 1 1 d .
N1 N 0.7075(3) 0.07133(11) 0.1310(4) 0.0272(7) Uani 1 1 d .
C1 C 0.1928(4) 0.15661(14) -0.1491(6) 0.0286(8) Uani 1 1 d .
C2 C 0.1893(4) 0.12791(14) 0.0386(5) 0.0253(8) Uani 1 1 d .
C3 C 0.0628(4) 0.13450(15) 0.0982(6) 0.0331(9) Uani 1 1 d .
H3 H 0.0571 0.1162 0.2220 0.040 Uiso 1 1 calc R
C4 C -0.0526(4) 0.16676(16) -0.0177(7) 0.0422(10) Uani 1 1 d .
H4 H -0.1345 0.1699 0.0269 0.051 Uiso 1 1 calc R
C5 C -0.0452(4) 0.19437(17) -0.2004(7) 0.0449(11) Uani 1 1 d .
H5 H -0.1223 0.2164 -0.2802 0.054 Uiso 1 1 calc R
C6 C 0.0764(4) 0.18929(16) -0.2649(6) 0.0396(10) Uani 1 1 d .
H6 H 0.0805 0.2081 -0.3885 0.048 Uiso 1 1 calc R
C7 C 0.3025(4) 0.08933(14) 0.1812(5) 0.0265(8) Uani 1 1 d .
C8 C 0.3220(4) 0.18758(15) -0.3926(5) 0.0309(8) Uani 1 1 d .
H8A H 0.3082 0.2269 -0.3588 0.037 Uiso 1 1 calc R
H8B H 0.2459 0.1774 -0.5227 0.037 Uiso 1 1 calc R
C9 C 0.4673(4) 0.18096(15) -0.4305(6) 0.0302(9) Uani 1 1 d .
C10 C 0.7856(3) 0.03275(14) 0.0661(5) 0.0274(8) Uani 1 1 d .
H10 H 0.7617 0.0247 -0.0806 0.033 Uiso 1 1 calc R
C11 C 0.8992(4) 0.00427(14) 0.2042(5) 0.0262(8) Uani 1 1 d .
H11 H 0.9495 -0.0225 0.1500 0.031 Uiso 1 1 calc R
C12 C 0.9399(3) 0.01492(13) 0.4233(5) 0.0230(8) Uani 1 1 d .
C13 C 0.8596(4) 0.05613(15) 0.4900(6) 0.0330(9) Uani 1 1 d .
H13 H 0.8829 0.0657 0.6353 0.040 Uiso 1 1 calc R
C14 C 0.7472(4) 0.08253(15) 0.3434(6) 0.0354(9) Uani 1 1 d .
H14 H 0.6954 0.1097 0.3930 0.042 Uiso 1 1 calc R
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_3
O3 Co1 O6 162.82(10) .
O3 Co1 N1 87.89(10) .
O6 Co1 N1 109.27(10) .
O3 Co1 O2 94.34(11) .
O6 Co1 O2 85.79(10) .
N1 Co1 O2 92.71(10) .
O3 Co1 O1 96.21(10) .
O6 Co1 O1 84.60(10) .
N1 Co1 O1 86.14(10) .
O2 Co1 O1 169.34(11) .
O3 Co1 O5 84.24(9) .
O6 Co1 O5 78.64(9) .
N1 Co1 O5 169.33(10) .
O2 Co1 O5 95.06(10) .
O1 Co1 O5 87.56(10) .
Co1 O1 H1A 115(2) .
Co1 O1 H1B 111(2) .
H1A O1 H1B 110.4(16) .
Co1 O2 H2A 129(2) .
Co1 O2 H2B 119(2) .
H2A O2 H2B 111.8(17) .
C7 O3 Co1 136.5(2) .
C1 O5 C8 117.5(3) .
C1 O5 Co1 130.1(2) .
C8 O5 Co1 111.55(19) .
C9 O6 Co1 118.2(2) .
C10 N1 C14 116.5(3) .
C10 N1 Co1 124.7(2) .
C14 N1 Co1 118.5(2) .
O5 C1 C6 120.5(3) .
O5 C1 C2 119.1(3) .
C6 C1 C2 120.4(3) .
C1 C2 C3 116.2(3) .
C1 C2 C7 128.1(3) .
C3 C2 C7 115.7(3) .
C4 C3 C2 123.2(4) .
C4 C3 H3 118.4 .
C2 C3 H3 118.4 .
C3 C4 C5 119.0(4) .
C3 C4 H4 120.5 .
C5 C4 H4 120.5 .
C4 C5 C6 119.9(4) .
C4 C5 H5 120.0 .
C6 C5 H5 120.0 .
C5 C6 C1 121.3(4) .
C5 C6 H6 119.4 .
C1 C6 H6 119.4 .
O4 C7 O3 121.9(3) .
O4 C7 C2 117.3(3) .
O3 C7 C2 120.8(3) .
O5 C8 C9 110.3(3) .
O5 C8 H8A 109.6 .
C9 C8 H8A 109.6 .
O5 C8 H8B 109.6 .
C9 C8 H8B 109.6 .
H8A C8 H8B 108.1 .
O6 C9 O7 125.5(3) .
O6 C9 C8 121.1(3) .
O7 C9 C8 113.4(3) .
N1 C10 C11 123.4(3) .
N1 C10 H10 118.3 .
C11 C10 H10 118.3 .
C10 C11 C12 120.6(3) .
C10 C11 H11 119.7 .
C12 C11 H11 119.7 .
C11 C12 C13 115.8(3) .
C11 C12 C12 122.3(4) 3_756
C13 C12 C12 121.9(4) 3_756
C14 C13 C12 120.4(3) .
C14 C13 H13 119.8 .
C12 C13 H13 119.8 .
N1 C14 C13 123.3(3) .
N1 C14 H14 118.3 .
C13 C14 H14 118.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 O3 1.994(2) .
Co1 O6 2.031(2) .
Co1 N1 2.090(3) .
Co1 O2 2.093(2) .
Co1 O1 2.138(3) .
Co1 O5 2.183(2) .
O1 H1A 0.850(10) .
O1 H1B 0.853(10) .
O2 H2A 0.846(10) .
O2 H2B 0.848(10) .
O3 C7 1.272(4) .
O4 C7 1.237(4) .
O5 C1 1.385(4) .
O5 C8 1.441(4) .
O6 C9 1.243(4) .
O7 C9 1.252(4) .
N1 C10 1.332(4) .
N1 C14 1.343(4) .
C1 C6 1.387(5) .
C1 C2 1.404(5) .
C2 C3 1.407(5) .
C2 C7 1.509(5) .
C3 C4 1.375(5) .
C3 H3 0.9300 .
C4 C5 1.375(5) .
C4 H4 0.9300 .
C5 C6 1.376(5) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C8 C9 1.516(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C10 C11 1.369(5) .
C10 H10 0.9300 .
C11 C12 1.382(4) .
C11 H11 0.9300 .
C12 C13 1.394(4) .
C12 C12 1.465(6) 3_756
C13 C14 1.363(5) .
C13 H13 0.9300 .
C14 H14 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1B O7 0.853(10) 1.829(15) 2.648(3) 161(3) 1_556
O1 H1A O7 0.850(10) 1.966(14) 2.794(3) 164(3) 4_566
O2 H2B O4 0.848(10) 1.919(12) 2.747(3) 165(3) 1_554
O2 H2A O3 0.846(10) 2.124(10) 2.963(3) 172(3) 3_655
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
_geom_torsion_site_symmetry_4
O6 Co1 O3 C7 -18.4(6) . .
N1 Co1 O3 C7 159.3(3) . .
O2 Co1 O3 C7 -108.1(3) . .
O1 Co1 O3 C7 73.4(3) . .
O5 Co1 O3 C7 -13.5(3) . .
O3 Co1 O5 C1 8.6(3) . .
O6 Co1 O5 C1 -172.9(3) . .
N1 Co1 O5 C1 -34.1(7) . .
O2 Co1 O5 C1 102.4(3) . .
O1 Co1 O5 C1 -87.9(3) . .
O3 Co1 O5 C8 176.9(2) . .
O6 Co1 O5 C8 -4.5(2) . .
N1 Co1 O5 C8 134.2(5) . .
O2 Co1 O5 C8 -89.2(2) . .
O1 Co1 O5 C8 80.4(2) . .
O3 Co1 O6 C9 9.2(5) . .
N1 Co1 O6 C9 -168.3(2) . .
O2 Co1 O6 C9 100.3(3) . .
O1 Co1 O6 C9 -84.3(2) . .
O5 Co1 O6 C9 4.3(2) . .
O3 Co1 N1 C10 121.6(3) . .
O6 Co1 N1 C10 -59.2(3) . .
O2 Co1 N1 C10 27.3(3) . .
O1 Co1 N1 C10 -142.1(3) . .
O5 Co1 N1 C10 164.0(4) . .
O3 Co1 N1 C14 -51.5(3) . .
O6 Co1 N1 C14 127.8(3) . .
O2 Co1 N1 C14 -145.8(3) . .
O1 Co1 N1 C14 44.9(3) . .
O5 Co1 N1 C14 -9.0(7) . .
C8 O5 C1 C6 8.5(5) . .
Co1 O5 C1 C6 176.3(2) . .
C8 O5 C1 C2 -171.8(3) . .
Co1 O5 C1 C2 -4.0(5) . .
O5 C1 C2 C3 -179.7(3) . .
C6 C1 C2 C3 0.1(5) . .
O5 C1 C2 C7 -1.7(5) . .
C6 C1 C2 C7 178.1(3) . .
C1 C2 C3 C4 0.2(5) . .
C7 C2 C3 C4 -178.0(3) . .
C2 C3 C4 C5 -0.4(6) . .
C3 C4 C5 C6 0.2(6) . .
C4 C5 C6 C1 0.1(6) . .
O5 C1 C6 C5 179.5(3) . .
C2 C1 C6 C5 -0.2(6) . .
Co1 O3 C7 O4 -169.1(2) . .
Co1 O3 C7 C2 12.5(5) . .
C1 C2 C7 O4 179.9(3) . .
C3 C2 C7 O4 -2.1(5) . .
C1 C2 C7 O3 -1.6(5) . .
C3 C2 C7 O3 176.4(3) . .
C1 O5 C8 C9 174.2(3) . .
Co1 O5 C8 C9 4.2(3) . .
Co1 O6 C9 O7 175.7(3) . .
Co1 O6 C9 C8 -3.2(4) . .
O5 C8 C9 O6 -1.0(5) . .
O5 C8 C9 O7 179.9(3) . .
C14 N1 C10 C11 1.3(5) . .
Co1 N1 C10 C11 -171.9(2) . .
N1 C10 C11 C12 -0.5(5) . .
C10 C11 C12 C13 -0.7(5) . .
C10 C11 C12 C12 179.5(4) . 3_756
C11 C12 C13 C14 1.1(5) . .
C12 C12 C13 C14 -179.1(4) 3_756 .
C10 N1 C14 C13 -0.9(5) . .
Co1 N1 C14 C13 172.8(3) . .
C12 C13 C14 N1 -0.4(6) . .
