#------------------------------------------------------------------------------
#$Date: 2016-04-05 18:26:19 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181606 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/41/7224172.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_7224172
loop_
_publ_author_name
'Chen, Li-Zhuang'
'Pan, Qi-Jian'
'Cao, Xing-Xing'
'Wang, Fang-Ming'
_publ_section_title
;
 Crystal structure, magnetism, and dielectric properties based on the
 axially chiral ligand
 2,2′-dinitro-4,4′-biphenyldicarboxylic acid
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1944
_journal_paper_doi               10.1039/C5CE02426A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C12 H7 Co0.5 N2 O4.18'
_chemical_formula_sum            'C12 H7 Co0.5 N2 O4.18'
_chemical_formula_weight         275.54
_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             2015-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-02 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.639(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.641(4)
_cell_length_b                   19.536(5)
_cell_length_c                   8.806(2)
_cell_measurement_reflns_used    3881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.82
_cell_volume                     2331.0(11)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9086
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.82
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9765
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.856
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.237
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0486
_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)+(0.0671P)²+8.7857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                1997
_reflns_number_total             2281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce02426a2.cif
_cod_data_source_block           2222
_cod_depositor_comments
'Adding full bibliography for 7224168--7224173.cif.'
_cod_original_formula_sum        'C12 H7 Co0.50 N2 O4.18'
_cod_database_code               7224172
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 O28, N15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N15, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
O28 \\sim N15: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N15) \\sim Ueq, Uanis(O5C) \\sim Ueq, Uanis(O5D) \\sim Ueq, Uanis(O28)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(O5D)=1-FVAR(1)
 Sof(O5C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C18(H18), C20(H20), C23(H23), C33(H33)
;
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Co1 Co 0.0000 -0.05667(3) 1.2500 0.0178(2) Uani 1 d . . 2 S T P
O1 O 0.07981(18) 0.02150(14) 1.1586(3) 0.0305(6) Uani 1 d . . 1 . . .
O2 O -0.10988(17) -0.06371(14) 1.0666(3) 0.0283(6) Uani 1 d . . 1 . . .
H8 H 0.272(5) 0.128(3) 0.981(7) 0.08(3) Uiso 1.00(14) d A 1 1 . U .
O28 O 0.4086(3) 0.2109(3) 0.9757(6) 0.0797(11) Uani 1 d . . 1 . U .
N3 N 0.0847(2) -0.13316(15) 1.1466(3) 0.0258(6) Uani 1 d . . 1 . . .
N15 N 0.4535(3) 0.1603(2) 1.0306(5) 0.0521(9) Uani 1 d B . 1 . U .
C1 C 0.1341(2) 0.04559(16) 1.0684(4) 0.0199(7) Uani 1 d . . 1 . . .
C2 C 0.2869(3) 0.0155(3) 1.2443(5) 0.0444(12) Uani 1 d B . 1 . . .
H2 H 0.2496 -0.0158 1.2929 0.053 Uiso 1 calc . . 1 R . .
C3 C 0.1679(4) -0.1741(2) 0.9412(5) 0.0486(13) Uani 1 d . . 1 . . .
H3 H 0.1790 -0.1696 0.8395 0.058 Uiso 1 calc . . 1 R . .
C5 C 0.2424(2) 0.05534(18) 1.1264(4) 0.0241(7) Uani 1 d . . 1 . . .
C8 C 0.2987(3) 0.1025(2) 1.0583(4) 0.0262(8) Uani 1 d B . 1 . . .
C9 C 0.4456(3) 0.0687(2) 1.2245(5) 0.0344(9) Uani 1 d . . 1 . . .
C10 C 0.2154(3) -0.22543(19) 1.0303(4) 0.0299(8) Uani 1 d . . 1 . . .
C14 C 0.3984(3) 0.1094(2) 1.1079(4) 0.0313(8) Uani 1 d . . 1 . U .
C18 C 0.1042(3) -0.1297(2) 1.0022(5) 0.0407(10) Uani 1 d . . 1 . . .
H18 H 0.0735 -0.0958 0.9395 0.049 Uiso 1 calc . . 1 R . .
C20 C 0.1945(3) -0.2287(2) 1.1806(5) 0.0358(9) Uani 1 d . . 1 . . .
H20 H 0.2245 -0.2618 1.2462 0.043 Uiso 1 calc . . 1 R . .
C23 C 0.1292(3) -0.1828(2) 1.2326(4) 0.0334(9) Uani 1 d . . 1 . . .
H23 H 0.1155 -0.1867 1.3333 0.040 Uiso 1 calc . . 1 R . .
C33 C 0.3872(3) 0.0222(3) 1.2905(6) 0.0520(13) Uani 1 d . . 1 . . .
H33 H 0.4162 -0.0057 1.3688 0.062 Uiso 1 calc B . 1 R . .
O5B O 0.431(2) 0.1674(14) 0.889(3) 0.082(12) Uiso 0.180(16) d B 3 1 . U .
O5C O 0.5407(4) 0.1470(4) 1.0106(8) 0.068(2) Uani 0.641(14) d B 4 1 . U .
O5D O 0.5279(9) 0.1842(6) 1.0931(15) 0.066(4) Uani 0.359(14) d B 5 1 . U .
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
O1 Co1 O1 86.10(15) . 2_557
O1 Co1 N3 90.89(11) . .
O1 Co1 N3 176.77(11) 2_557 .
O1 Co1 N3 176.77(11) . 2_557
O1 Co1 N3 90.89(11) 2_557 2_557
O2 Co1 O1 96.33(10) . .
O2 Co1 O1 89.23(10) 2_557 .
O2 Co1 O1 89.23(10) . 2_557
O2 Co1 O1 96.33(10) 2_557 2_557
O2 Co1 O2 172.41(15) 2_557 .
O2 Co1 N3 84.77(11) 2_557 .
O2 Co1 N3 89.96(11) . .
O2 Co1 N3 89.96(11) 2_557 2_557
O2 Co1 N3 84.77(11) . 2_557
N3 Co1 N3 92.15(17) 2_557 .
C1 O1 Co1 154.2(2) . .
C1 O2 Co1 144.1(2) 5_557 .
O5B O28 N15 62.0(13) . .
C18 N3 Co1 123.0(3) . .
C18 N3 C23 116.9(3) . .
C23 N3 Co1 119.7(2) . .
O28 N15 C14 118.0(4) . .
O28 N15 O5B 57.8(13) . .
O28 N15 O5C 123.3(5) . .
O5B N15 C14 117.1(13) . .
O5C N15 C14 118.3(5) . .
O5C N15 O5B 90.8(13) . .
O5D N15 O28 103.0(7) . .
O5D N15 C14 120.5(7) . .
O5D N15 O5B 120.9(14) . .
O5D N15 O5C 51.1(7) . .
O1 C1 O2 127.3(3) . 5_557
O1 C1 C5 117.5(3) . .
O2 C1 C5 115.2(3) 5_557 .
C5 C2 H2 120.0 . .
C5 C2 C33 120.0(4) . .
C33 C2 H2 120.0 . .
C10 C3 H3 119.7 . .
C18 C3 H3 119.7 . .
C18 C3 C10 120.6(4) . .
C2 C5 C1 120.6(3) . .
C8 C5 C1 120.4(3) . .
C8 C5 C2 119.0(3) . .
C5 C8 H8 121(4) . .
C5 C8 C14 120.2(4) . .
C14 C8 H8 119(4) . .
C14 C9 C9 125.2(4) . 2_657
C33 C9 C9 118.2(3) . 2_657
C33 C9 C14 116.5(3) . .
C3 C10 C10 122.6(4) . 7_547
C3 C10 C20 116.0(3) . .
C20 C10 C10 121.4(4) . 7_547
C8 C14 N15 117.2(4) . .
C8 C14 C9 121.9(4) . .
C9 C14 N15 120.8(3) . .
N3 C18 C3 123.0(4) . .
N3 C18 H18 118.5 . .
C3 C18 H18 118.5 . .
C10 C20 H20 120.1 . .
C23 C20 C10 119.9(4) . .
C23 C20 H20 120.1 . .
N3 C23 C20 123.6(4) . .
N3 C23 H23 118.2 . .
C20 C23 H23 118.2 . .
C2 C33 H33 118.8 . .
C9 C33 C2 122.4(4) . .
C9 C33 H33 118.8 . .
O28 O5B N15 60.2(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 O1 2.090(3) .
Co1 O1 2.090(3) 2_557
Co1 O2 2.077(2) 2_557
Co1 O2 2.077(2) .
Co1 N3 2.154(3) .
Co1 N3 2.154(3) 2_557
O1 C1 1.240(4) .
O2 C1 1.247(4) 5_557
O28 N15 1.232(6) .
O28 O5B 1.20(3) .
N3 C18 1.331(5) .
N3 C23 1.333(5) .
N15 C14 1.461(6) .
N15 O5B 1.25(3) .
N15 O5C 1.250(7) .
N15 O5D 1.192(12) .
C1 O2 1.247(4) 5_557
C1 C5 1.518(4) .
C2 H2 0.9300 .
C2 C5 1.381(5) .
C2 C33 1.388(6) .
C3 H3 0.9300 .
C3 C10 1.387(5) .
C3 C18 1.380(6) .
C5 C8 1.381(5) .
C8 H8 0.89(6) .
C8 C14 1.386(5) .
C9 C9 1.500(7) 2_657
C9 C14 1.396(6) .
C9 C33 1.380(6) .
C10 C10 1.487(7) 7_547
C10 C20 1.387(5) .
C18 H18 0.9300 .
C20 H20 0.9300 .
C20 C23 1.380(5) .
C23 H23 0.9300 .
C33 H33 0.9300 .
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
Co1 O1 C1 O2 79.3(7) . 5_557
Co1 O1 C1 C5 -101.4(5) . .
Co1 N3 C18 C3 172.1(4) . .
Co1 N3 C23 C20 -171.7(3) . .
O1 Co1 O1 C1 -159.7(6) 2_557 .
O1 Co1 O2 C1 11.6(4) . 5_557
O1 Co1 O2 C1 97.6(4) 2_557 5_557
O1 Co1 N3 C18 -45.8(3) . .
O1 Co1 N3 C18 -25(2) 2_557 .
O1 Co1 N3 C23 126.7(3) . .
O1 Co1 N3 C23 147.7(18) 2_557 .
O1 C1 C5 C2 25.8(5) . .
O1 C1 C5 C8 -156.5(3) . .
O2 Co1 O1 C1 -70.9(5) . .
O2 Co1 O1 C1 104.0(5) 2_557 .
O2 Co1 O2 C1 -125.2(4) 2_557 5_557
O2 Co1 N3 C18 -135.0(3) 2_557 .
O2 Co1 N3 C18 50.5(3) . .
O2 Co1 N3 C23 37.6(3) 2_557 .
O2 Co1 N3 C23 -136.9(3) . .
O2 C1 C5 C2 -154.8(4) 5_557 .
O2 C1 C5 C8 22.9(5) 5_557 .
O28 N15 C14 C8 29.0(6) . .
O28 N15 C14 C9 -152.3(5) . .
N3 Co1 O1 C1 19.2(5) . .
N3 Co1 O1 C1 179(100) 2_557 .
N3 Co1 O2 C1 -171.4(4) 2_557 5_557
N3 Co1 O2 C1 -79.3(4) . 5_557
N3 Co1 N3 C18 135.3(4) 2_557 .
N3 Co1 N3 C23 -52.2(3) 2_557 .
C1 C5 C8 C14 -177.5(3) . .
C2 C5 C8 C14 0.2(6) . .
C3 C10 C20 C23 0.5(7) . .
C5 C2 C33 C9 1.3(8) . .
C5 C8 C14 N15 179.9(4) . .
C5 C8 C14 C9 1.3(6) . .
C9 C9 C14 N15 -4.2(6) 2_657 .
C9 C9 C14 C8 174.5(4) 2_657 .
C9 C9 C33 C2 -176.0(5) 2_657 .
C10 C3 C18 N3 -0.1(8) . .
C10 C10 C20 C23 -179.3(5) 7_547 .
C10 C20 C23 N3 -1.3(7) . .
C14 N15 O5B O28 107.5(10) . .
C14 C9 C33 C2 0.1(8) . .
C18 N3 C23 C20 1.3(6) . .
C18 C3 C10 C10 179.9(5) . 7_547
C18 C3 C10 C20 0.2(7) . .
C23 N3 C18 C3 -0.7(7) . .
C33 C2 C5 C1 176.3(4) . .
C33 C2 C5 C8 -1.4(7) . .
C33 C9 C14 N15 180.0(4) . .
C33 C9 C14 C8 -1.4(6) . .
O5B O28 N15 C14 -106.0(15) . .
O5B O28 N15 O5C 66.8(16) . .
O5B O28 N15 O5D 118.6(17) . .
O5B N15 C14 C8 -37.0(16) . .
O5B N15 C14 C9 141.7(15) . .
O5C N15 C14 C8 -144.1(6) . .
O5C N15 C14 C9 34.6(7) . .
O5C N15 O5B O28 -129.8(9) . .
O5D N15 C14 C8 156.5(9) . .
O5D N15 C14 C9 -24.8(10) . .
O5D N15 O5B O28 -86.1(15) . .
