#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:56:51 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179432 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/29/4332912.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4332912
loop_
_publ_author_name
'Min, Kil Sik'
'Rheingold, Arnold L.'
'DiPasquale, Antonio'
'Miller, Joel S.'
_publ_section_title
;
 Characterization of the Chloranilate(•3−)\pRadical as a
 Strong Spin-Coupling Bridging Ligand
;
_journal_issue                   16
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6135
_journal_page_last               6137
_journal_paper_doi               10.1021/ic061076k
_journal_volume                  45
_journal_year                    2006
_chemical_formula_sum            'C50 H56 B Cl2 Co2 F4 N8 O6'
_chemical_formula_weight         1140.60
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/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                 90.687(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.846(7)
_cell_length_b                   11.493(6)
_cell_length_c                   15.958(8)
_cell_measurement_reflns_used    5523
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.55
_cell_volume                     2539(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.913
_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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10900
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.9215
_exptl_absorpt_correction_T_min  0.9215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1178
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0469
_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)+(0.0804P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                4456
_reflns_number_total             5750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic061076ksup1.cif
_cod_data_source_block           jsm120
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               4332912
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
C1 C 0.0674(2) 0.1313(2) 0.40845(18) 0.0447(6) Uani 1 1 d .
H1 H 0.0428 0.2045 0.3929 0.054 Uiso 1 1 calc R
C2 C 0.0186(2) 0.0332(2) 0.3829(2) 0.0587(8) Uani 1 1 d .
H2 H -0.0379 0.0396 0.3500 0.070 Uiso 1 1 calc R
C3 C 0.0530(3) -0.0743(2) 0.4058(2) 0.0629(9) Uani 1 1 d .
H3 H 0.0207 -0.1426 0.3892 0.075 Uiso 1 1 calc R
C4 C 0.1360(3) -0.0789(2) 0.4537(2) 0.0600(9) Uani 1 1 d .
H4 H 0.1611 -0.1514 0.4704 0.072 Uiso 1 1 calc R
C5 C 0.1828(2) 0.0223(2) 0.47734(17) 0.0473(7) Uani 1 1 d .
C6 C 0.2750(3) 0.0209(2) 0.5280(2) 0.0770(12) Uani 1 1 d .
H6A H 0.2636 -0.0213 0.5804 0.092 Uiso 1 1 calc R
H6B H 0.3239 -0.0224 0.4968 0.092 Uiso 1 1 calc R
C7 C 0.33420(19) 0.3256(2) 0.33511(17) 0.0415(6) Uani 1 1 d .
H7 H 0.2817 0.3743 0.3216 0.050 Uiso 1 1 calc R
C8 C 0.4069(2) 0.3161(2) 0.2785(2) 0.0504(7) Uani 1 1 d .
H8 H 0.4040 0.3563 0.2272 0.060 Uiso 1 1 calc R
C9 C 0.4848(2) 0.2460(3) 0.2984(2) 0.0522(7) Uani 1 1 d .
H9 H 0.5363 0.2378 0.2610 0.063 Uiso 1 1 calc R
C10 C 0.4858(2) 0.1884(3) 0.3741(2) 0.0547(7) Uani 1 1 d .
H10 H 0.5377 0.1396 0.3889 0.066 Uiso 1 1 calc R
C11 C 0.4099(2) 0.2030(2) 0.42774(18) 0.0466(6) Uani 1 1 d .
C12 C 0.4123(2) 0.1542(3) 0.5150(2) 0.0674(10) Uani 1 1 d .
H12A H 0.4471 0.0799 0.5148 0.081 Uiso 1 1 calc R
H12B H 0.4477 0.2078 0.5519 0.081 Uiso 1 1 calc R
C13 C 0.29234(19) 0.4724(2) 0.60802(18) 0.0427(6) Uani 1 1 d .
H13 H 0.2644 0.5214 0.5673 0.051 Uiso 1 1 calc R
C14 C 0.3365(2) 0.5220(2) 0.6769(2) 0.0546(7) Uani 1 1 d .
H14 H 0.3380 0.6033 0.6836 0.065 Uiso 1 1 calc R
C15 C 0.3781(2) 0.4507(3) 0.7351(2) 0.0578(8) Uani 1 1 d .
H15 H 0.4092 0.4826 0.7825 0.069 Uiso 1 1 calc R
C16 C 0.3745(2) 0.3321(3) 0.72471(18) 0.0520(7) Uani 1 1 d .
H16 H 0.4030 0.2821 0.7646 0.062 Uiso 1 1 calc R
C17 C 0.3282(2) 0.2876(2) 0.65442(17) 0.0417(6) Uani 1 1 d .
C18 C 0.3148(2) 0.1601(2) 0.63899(18) 0.0486(7) Uani 1 1 d .
H18A H 0.3675 0.1168 0.6660 0.058 Uiso 1 1 calc R
H18B H 0.2539 0.1344 0.6636 0.058 Uiso 1 1 calc R
C19 C 0.08560(16) 0.45672(17) 0.46321(14) 0.0288(4) Uani 1 1 d .
C20 C 0.04359(16) 0.39698(16) 0.53589(14) 0.0291(4) Uani 1 1 d .
C21 C -0.04113(16) 0.44436(17) 0.56854(14) 0.0294(4) Uani 1 1 d .
B1 B 0.2500 0.8585(4) 0.7500 0.0580(13) Uani 1 2 d S
N1 N 0.14830(16) 0.12666(16) 0.45441(13) 0.0391(5) Uani 1 1 d .
N2 N 0.31346(17) 0.13546(18) 0.54843(14) 0.0460(5) Uani 1 1 d .
N3 N 0.28748(14) 0.35696(16) 0.59657(13) 0.0365(4) Uani 1 1 d .
N4 N 0.33318(16) 0.26979(16) 0.40862(14) 0.0384(5) Uani 1 1 d .
O1 O 0.16382(11) 0.41167(12) 0.43215(10) 0.0333(4) Uani 1 1 d .
O2 O 0.08790(11) 0.30724(12) 0.56453(10) 0.0334(4) Uani 1 1 d .
F1 F 0.2437(4) 0.7903(3) 0.6836(2) 0.186(2) Uani 1 1 d .
F2 F 0.32751(15) 0.9294(2) 0.7494(2) 0.1302(12) Uani 1 1 d .
Cl1 Cl -0.09512(4) 0.37487(5) 0.65298(4) 0.03842(16) Uani 1 1 d .
Co1 Co 0.21854(2) 0.27760(2) 0.49430(2) 0.03224(12) 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
N1 C1 C2 122.5(3) . .
N1 C1 H1 118.7 . .
C2 C1 H1 118.7 . .
C3 C2 C1 119.5(3) . .
C3 C2 H2 120.2 . .
C1 C2 H2 120.2 . .
C2 C3 C4 117.9(3) . .
C2 C3 H3 121.0 . .
C4 C3 H3 121.0 . .
C3 C4 C5 120.4(3) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
N1 C5 C4 120.9(3) . .
N1 C5 C6 117.1(2) . .
C4 C5 C6 122.0(2) . .
N2 C6 C5 114.6(2) . .
N2 C6 H6A 108.6 . .
C5 C6 H6A 108.6 . .
N2 C6 H6B 108.6 . .
C5 C6 H6B 108.6 . .
H6A C6 H6B 107.6 . .
N4 C7 C8 123.9(2) . .
N4 C7 H7 118.1 . .
C8 C7 H7 118.1 . .
C7 C8 C9 118.3(3) . .
C7 C8 H8 120.8 . .
C9 C8 H8 120.8 . .
C10 C9 C8 118.8(3) . .
C10 C9 H9 120.6 . .
C8 C9 H9 120.6 . .
C11 C10 C9 119.2(3) . .
C11 C10 H10 120.4 . .
C9 C10 H10 120.4 . .
N4 C11 C10 122.5(3) . .
N4 C11 C12 115.7(2) . .
C10 C11 C12 121.5(3) . .
N2 C12 C11 112.0(2) . .
N2 C12 H12A 109.2 . .
C11 C12 H12A 109.2 . .
N2 C12 H12B 109.2 . .
C11 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
N3 C13 C14 122.7(3) . .
N3 C13 H13 118.6 . .
C14 C13 H13 118.6 . .
C15 C14 C13 118.4(3) . .
C15 C14 H14 120.8 . .
C13 C14 H14 120.8 . .
C14 C15 C16 120.1(3) . .
C14 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
C15 C16 C17 118.7(3) . .
C15 C16 H16 120.7 . .
C17 C16 H16 120.7 . .
N3 C17 C16 121.8(2) . .
N3 C17 C18 114.8(2) . .
C16 C17 C18 123.4(2) . .
N2 C18 C17 110.5(2) . .
N2 C18 H18A 109.6 . .
C17 C18 H18A 109.6 . .
N2 C18 H18B 109.6 . .
C17 C18 H18B 109.6 . .
H18A C18 H18B 108.1 . .
O1 C19 C21 123.7(2) . 3_566
O1 C19 C20 116.86(18) . .
C21 C19 C20 119.5(2) 3_566 .
O2 C20 C21 125.5(2) . .
O2 C20 C19 117.64(19) . .
C21 C20 C19 116.89(18) . .
C19 C21 C20 123.6(2) 3_566 .
C19 C21 Cl1 117.76(17) 3_566 .
C20 C21 Cl1 118.61(16) . .
F1 B1 F1 107.1(4) 2_556 .
F1 B1 F2 108.6(2) 2_556 .
F1 B1 F2 113.5(3) . .
F1 B1 F2 113.5(3) 2_556 2_556
F1 B1 F2 108.6(2) . 2_556
F2 B1 F2 105.7(3) . 2_556
C1 N1 C5 118.7(2) . .
C1 N1 Co1 121.40(16) . .
C5 N1 Co1 119.84(19) . .
C6 N2 C18 113.2(3) . .
C6 N2 C12 112.6(3) . .
C18 N2 C12 108.9(2) . .
C6 N2 Co1 111.03(18) . .
C18 N2 Co1 103.65(15) . .
C12 N2 Co1 106.91(16) . .
C17 N3 C13 118.4(2) . .
C17 N3 Co1 117.59(16) . .
C13 N3 Co1 124.05(18) . .
C7 N4 C11 117.2(2) . .
C7 N4 Co1 124.34(17) . .
C11 N4 Co1 118.44(18) . .
C19 O1 Co1 115.70(14) . .
C20 O2 Co1 109.95(14) . .
O1 Co1 N1 108.70(8) . .
O1 Co1 N3 102.71(7) . .
N1 Co1 N3 143.95(8) . .
O1 Co1 N4 89.70(7) . .
N1 Co1 N4 96.81(8) . .
N3 Co1 N4 100.63(9) . .
O1 Co1 O2 79.62(7) . .
N1 Co1 O2 84.23(7) . .
N3 Co1 O2 84.48(8) . .
N4 Co1 O2 168.99(7) . .
O1 Co1 N2 166.25(8) . .
N1 Co1 N2 77.43(9) . .
N3 Co1 N2 76.06(8) . .
N4 Co1 N2 77.20(9) . .
O2 Co1 N2 113.64(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.332(3) .
C1 C2 1.374(4) .
C1 H1 0.9400 .
C2 C3 1.371(4) .
C2 H2 0.9400 .
C3 C4 1.374(5) .
C3 H3 0.9400 .
C4 C5 1.382(4) .
C4 H4 0.9400 .
C5 N1 1.340(3) .
C5 C6 1.503(5) .
C6 N2 1.456(4) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C7 N4 1.337(3) .
C7 C8 1.365(4) .
C7 H7 0.9400 .
C8 C9 1.380(4) .
C8 H8 0.9400 .
C9 C10 1.378(4) .
C9 H9 0.9400 .
C10 C11 1.374(4) .
C10 H10 0.9400 .
C11 N4 1.343(3) .
C11 C12 1.501(4) .
C12 N2 1.491(4) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C13 N3 1.341(3) .
C13 C14 1.375(4) .
C13 H13 0.9400 .
C14 C15 1.362(4) .
C14 H14 0.9400 .
C15 C16 1.374(4) .
C15 H15 0.9400 .
C16 C17 1.383(4) .
C16 H16 0.9400 .
C17 N3 1.339(3) .
C17 C18 1.497(4) .
C18 N2 1.473(4) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C19 O1 1.304(3) .
C19 C21 1.386(3) 3_566
C19 C20 1.473(3) .
C20 O2 1.282(2) .
C20 C21 1.400(3) .
C21 C19 1.386(3) 3_566
C21 Cl1 1.743(2) .
B1 F1 1.320(4) 2_556
B1 F1 1.320(4) .
B1 F2 1.347(3) .
B1 F2 1.347(3) 2_556
N1 Co1 2.085(2) .
N2 Co1 2.262(2) .
N3 Co1 2.090(2) .
N4 Co1 2.109(2) .
O1 Co1 1.9783(16) .
O2 Co1 2.1662(18) .
