#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:13:21 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179472 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/69/4336983.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_4336983
loop_
_publ_author_name
'Laleh Tahsini'
'Sarah E. Specht'
'June S. Lum'
'Joshua J. M. Nelson'
'Alexandra F. Long'
'James A. Golen'
'Arnold L. Rheingold'
'Linda H. Doerrer'
_publ_section_title
;
 Structural and Electronic Properties of Old and New A2[M(pinF)2]
 Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              14050
_journal_page_last               14063
_journal_paper_doi               10.1021/ic401837y
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C20 H24 Co F24 N2 O4'
_chemical_formula_weight         871.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 115.402(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.2586(13)
_cell_length_b                   8.2481(6)
_cell_length_c                   18.8198(12)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.40
_cell_volume                     2980.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21076
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.14
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.9488
_exptl_absorpt_correction_T_min  0.8212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_description       blade
_exptl_crystal_F_000             1732
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+19.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                4835
_reflns_number_total             5868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401837y_si_002_2.cif
_cod_data_source_block           lhd328_Compound_2
_cod_database_code               4336983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -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
Co1 Co 0.5000 0.48894(10) 0.2500 0.01349(19) Uani 1 2 d S
Co2 Co 0.0000 -0.05105(10) -0.2500 0.01300(18) Uani 1 2 d S
F1 F 0.38408(14) 0.4512(3) 0.41206(15) 0.0235(6) Uani 1 1 d .
F2 F 0.46647(13) 0.6218(3) 0.43469(14) 0.0233(6) Uani 1 1 d .
F3 F 0.47515(13) 0.3833(3) 0.39534(15) 0.0228(6) Uani 1 1 d .
F4 F 0.28570(12) 0.6408(3) 0.29960(15) 0.0193(5) Uani 1 1 d .
F5 F 0.31877(14) 0.7806(3) 0.22558(15) 0.0231(6) Uani 1 1 d .
F6 F 0.36990(13) 0.8089(3) 0.35009(15) 0.0236(6) Uani 1 1 d .
F7 F 0.30566(14) 0.3567(3) 0.09827(15) 0.0254(6) Uani 1 1 d .
F8 F 0.34574(13) 0.5958(3) 0.12937(14) 0.0209(6) Uani 1 1 d .
F9 F 0.25479(12) 0.5212(3) 0.14467(15) 0.0221(6) Uani 1 1 d .
F10 F 0.29527(15) 0.1733(3) 0.19969(17) 0.0289(6) Uani 1 1 d .
F11 F 0.36842(14) 0.1916(3) 0.32046(17) 0.0263(6) Uani 1 1 d .
F12 F 0.27530(13) 0.3369(3) 0.27585(15) 0.0215(6) Uani 1 1 d .
F13 F 0.19891(13) 0.0747(3) -0.20325(15) 0.0248(6) Uani 1 1 d .
F14 F 0.24505(13) -0.0895(3) -0.10625(15) 0.0231(6) Uani 1 1 d .
F15 F 0.15650(13) -0.1621(3) -0.21310(14) 0.0214(6) Uani 1 1 d .
F16 F 0.20450(14) 0.2613(3) -0.09508(15) 0.0264(6) Uani 1 1 d .
F17 F 0.21889(13) 0.0994(3) -0.00018(14) 0.0200(6) Uani 1 1 d .
F18 F 0.12715(14) 0.2486(3) -0.05139(16) 0.0257(6) Uani 1 1 d .
F19 F 0.01857(13) 0.0582(3) -0.08482(15) 0.0223(6) Uani 1 1 d .
F20 F 0.02433(13) -0.1776(3) -0.03589(14) 0.0220(6) Uani 1 1 d .
F21 F 0.10708(14) -0.0074(3) 0.02368(14) 0.0236(6) Uani 1 1 d .
F22 F 0.17646(13) -0.3455(3) -0.09222(15) 0.0223(6) Uani 1 1 d .
F23 F 0.20836(13) -0.2032(3) 0.01321(14) 0.0215(6) Uani 1 1 d .
F24 F 0.12213(14) -0.3680(3) -0.02003(15) 0.0233(6) Uani 1 1 d .
O1 O 0.44790(15) 0.6388(4) 0.28584(17) 0.0157(6) Uani 1 1 d .
O2 O 0.42248(15) 0.3402(4) 0.23130(18) 0.0172(6) Uani 1 1 d .
O3 O 0.07779(15) 0.0967(4) -0.19212(16) 0.0162(6) Uani 1 1 d .
O4 O 0.04927(15) -0.2008(4) -0.16264(16) 0.0157(6) Uani 1 1 d .
N1 N 0.08330(19) -0.5505(4) -0.3280(2) 0.0169(8) Uani 1 1 d .
N2 N 0.42077(19) 0.9869(4) 0.0876(2) 0.0170(8) Uani 1 1 d .
C1 C 0.4294(2) 0.5025(6) 0.3853(2) 0.0181(9) Uani 1 1 d .
C2 C 0.3959(2) 0.5656(5) 0.2982(2) 0.0146(8) Uani 1 1 d .
C3 C 0.3418(2) 0.6975(5) 0.2927(2) 0.0165(9) Uani 1 1 d .
C4 C 0.3173(2) 0.4725(5) 0.1520(3) 0.0184(9) Uani 1 1 d .
C5 C 0.3664(2) 0.4121(5) 0.2362(2) 0.0153(9) Uani 1 1 d .
C6 C 0.3259(2) 0.2781(5) 0.2589(3) 0.0185(9) Uani 1 1 d .
C7 C 0.1834(2) -0.0397(6) -0.1627(2) 0.0180(9) Uani 1 1 d .
C8 C 0.1315(2) 0.0238(5) -0.1306(2) 0.0157(9) Uani 1 1 d .
C9 C 0.1706(2) 0.1584(5) -0.0686(3) 0.0192(9) Uani 1 1 d .
C10 C 0.0632(2) -0.0612(6) -0.0481(2) 0.0184(9) Uani 1 1 d .
C11 C 0.0997(2) -0.1266(5) -0.0985(2) 0.0146(8) Uani 1 1 d .
C12 C 0.1524(2) -0.2604(5) -0.0491(2) 0.0171(9) Uani 1 1 d .
C13 C 0.1159(2) -0.7000(6) -0.3421(3) 0.0217(10) Uani 1 1 d .
H13A H 0.0981 -0.7188 -0.3988 0.033 Uiso 1 1 calc R
H13B H 0.1043 -0.7930 -0.3175 0.033 Uiso 1 1 calc R
H13C H 0.1665 -0.6864 -0.3192 0.033 Uiso 1 1 calc R
C14 C 0.1089(2) -0.5247(6) -0.2410(2) 0.0196(9) Uani 1 1 d .
H14A H 0.0939 -0.6153 -0.2183 0.029 Uiso 1 1 calc R
H14B H 0.0897 -0.4233 -0.2316 0.029 Uiso 1 1 calc R
H14C H 0.1599 -0.5188 -0.2164 0.029 Uiso 1 1 calc R
C15 C 0.1004(2) -0.4050(6) -0.3635(3) 0.0211(10) Uani 1 1 d .
H15A H 0.1509 -0.3889 -0.3397 0.032 Uiso 1 1 calc R
H15B H 0.0779 -0.3092 -0.3539 0.032 Uiso 1 1 calc R
H15C H 0.0836 -0.4213 -0.4203 0.032 Uiso 1 1 calc R
C16 C 0.0058(2) -0.5720(6) -0.3631(3) 0.0209(10) Uani 1 1 d .
H16A H -0.0117 -0.5928 -0.4197 0.031 Uiso 1 1 calc R
H16B H -0.0158 -0.4733 -0.3548 0.031 Uiso 1 1 calc R
H16C H -0.0057 -0.6640 -0.3379 0.031 Uiso 1 1 calc R
C17 C 0.4044(3) 0.8398(6) 0.0366(3) 0.0245(10) Uani 1 1 d .
H17A H 0.4221 0.8541 -0.0032 0.037 Uiso 1 1 calc R
H17B H 0.3538 0.8240 0.0105 0.037 Uiso 1 1 calc R
H17C H 0.4264 0.7447 0.0689 0.037 Uiso 1 1 calc R
C18 C 0.3938(3) 1.1353(6) 0.0380(3) 0.0251(10) Uani 1 1 d .
H18A H 0.4154 1.1447 0.0014 0.038 Uiso 1 1 calc R
H18B H 0.4053 1.2313 0.0719 0.038 Uiso 1 1 calc R
H18C H 0.3432 1.1271 0.0082 0.038 Uiso 1 1 calc R
C19 C 0.3886(2) 0.9702(6) 0.1437(3) 0.0226(10) Uani 1 1 d .
H19A H 0.3381 0.9578 0.1143 0.034 Uiso 1 1 calc R
H19B H 0.3987 1.0672 0.1769 0.034 Uiso 1 1 calc R
H19C H 0.4079 0.8746 0.1769 0.034 Uiso 1 1 calc R
C20 C 0.4982(2) 1.0035(6) 0.1335(3) 0.0207(9) Uani 1 1 d .
H20A H 0.5167 0.9072 0.1664 0.031 Uiso 1 1 calc R
H20B H 0.5086 1.1001 0.1670 0.031 Uiso 1 1 calc R
H20C H 0.5199 1.0142 0.0971 0.031 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'
F F 0.0171 0.0103 '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'
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'
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 101.92(17) . 2_655
O1 Co1 O2 152.50(12) . 2_655
O1 Co1 O2 84.32(12) 2_655 2_655
O1 Co1 O2 84.32(12) . .
O1 Co1 O2 152.50(12) 2_655 .
O2 Co1 O2 102.55(17) 2_655 .
O4 Co2 O4 101.97(17) . 2_554
O4 Co2 O3 84.60(12) . .
O4 Co2 O3 151.03(12) 2_554 .
O4 Co2 O3 151.04(12) . 2_554
O4 Co2 O3 84.59(12) 2_554 2_554
O3 Co2 O3 103.35(17) . 2_554
C2 O1 Co1 113.5(3) . .
C5 O2 Co1 113.9(3) . .
C8 O3 Co2 113.3(3) . .
C11 O4 Co2 113.1(3) . .
C15 N1 C13 111.4(3) . .
C15 N1 C14 109.3(3) . .
C13 N1 C14 109.4(3) . .
C15 N1 C16 109.3(3) . .
C13 N1 C16 109.2(3) . .
C14 N1 C16 108.3(3) . .
C18 N2 C17 110.1(3) . .
C18 N2 C19 110.4(4) . .
C17 N2 C19 109.2(3) . .
C18 N2 C20 108.4(3) . .
C17 N2 C20 109.9(4) . .
C19 N2 C20 108.8(3) . .
F1 C1 F3 108.2(4) . .
F1 C1 F2 105.8(3) . .
F3 C1 F2 105.3(3) . .
F1 C1 C2 114.9(3) . .
F3 C1 C2 111.6(3) . .
F2 C1 C2 110.3(4) . .
O1 C2 C3 108.0(3) . .
O1 C2 C1 106.7(3) . .
C3 C2 C1 107.1(3) . .
O1 C2 C5 108.0(3) . .
C3 C2 C5 116.3(3) . .
C1 C2 C5 110.4(3) . .
F5 C3 F4 106.9(3) . .
F5 C3 F6 105.4(3) . .
F4 C3 F6 105.6(3) . .
F5 C3 C2 112.6(3) . .
F4 C3 C2 114.4(3) . .
F6 C3 C2 111.3(3) . .
F7 C4 F9 106.5(3) . .
F7 C4 F8 105.4(3) . .
F9 C4 F8 107.6(4) . .
F7 C4 C5 111.5(4) . .
F9 C4 C5 113.7(4) . .
F8 C4 C5 111.6(3) . .
O2 C5 C4 107.0(3) . .
O2 C5 C6 107.9(3) . .
C4 C5 C6 107.2(3) . .
O2 C5 C2 107.6(3) . .
C4 C5 C2 111.0(3) . .
C6 C5 C2 115.7(3) . .
F11 C6 F10 106.6(4) . .
F11 C6 F12 107.6(4) . .
F10 C6 F12 106.2(3) . .
F11 C6 C5 111.6(3) . .
F10 C6 C5 110.9(4) . .
F12 C6 C5 113.6(4) . .
F15 C7 F13 105.2(3) . .
F15 C7 F14 107.7(4) . .
F13 C7 F14 105.6(3) . .
F15 C7 C8 111.8(3) . .
F13 C7 C8 111.9(4) . .
F14 C7 C8 114.0(3) . .
O3 C8 C7 106.9(3) . .
O3 C8 C9 107.6(3) . .
C7 C8 C9 106.8(3) . .
O3 C8 C11 108.4(3) . .
C7 C8 C11 111.1(3) . .
C9 C8 C11 115.6(3) . .
F18 C9 F16 106.0(4) . .
F18 C9 F17 107.1(4) . .
F16 C9 F17 105.9(3) . .
F18 C9 C8 112.1(3) . .
F16 C9 C8 111.8(4) . .
F17 C9 C8 113.5(4) . .
F21 C10 F19 108.0(4) . .
F21 C10 F20 106.0(3) . .
F19 C10 F20 105.2(3) . .
F21 C10 C11 114.5(3) . .
F19 C10 C11 111.6(3) . .
F20 C10 C11 111.0(4) . .
O4 C11 C10 106.7(3) . .
O4 C11 C12 107.5(3) . .
C10 C11 C12 107.4(3) . .
O4 C11 C8 107.7(3) . .
C10 C11 C8 110.6(3) . .
C12 C11 C8 116.5(3) . .
F22 C12 F24 106.1(3) . .
F22 C12 F23 106.8(3) . .
F24 C12 F23 106.0(3) . .
F22 C12 C11 112.0(3) . .
F24 C12 C11 111.2(3) . .
F23 C12 C11 114.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 O1 1.962(3) .
Co1 O1 1.962(3) 2_655
Co1 O2 1.962(3) 2_655
Co1 O2 1.962(3) .
Co2 O4 1.961(3) .
Co2 O4 1.961(3) 2_554
Co2 O3 1.965(3) .
Co2 O3 1.965(3) 2_554
F1 C1 1.334(5) .
F2 C1 1.351(5) .
F3 C1 1.337(5) .
F4 C3 1.338(5) .
F5 C3 1.333(5) .
F6 C3 1.346(5) .
F7 C4 1.335(5) .
F8 C4 1.342(5) .
F9 C4 1.337(5) .
F10 C6 1.338(5) .
F11 C6 1.330(5) .
F12 C6 1.338(5) .
F13 C7 1.341(5) .
F14 C7 1.349(5) .
F15 C7 1.334(5) .
F16 C9 1.340(5) .
F17 C9 1.347(5) .
F18 C9 1.330(5) .
F19 C10 1.336(5) .
F20 C10 1.349(5) .
F21 C10 1.345(5) .
F22 C12 1.329(5) .
F23 C12 1.347(5) .
F24 C12 1.343(5) .
O1 C2 1.364(5) .
O2 C5 1.370(5) .
O3 C8 1.368(5) .
O4 C11 1.367(5) .
N1 C15 1.493(6) .
N1 C13 1.493(6) .
N1 C14 1.502(5) .
N1 C16 1.499(5) .
N2 C18 1.496(6) .
N2 C17 1.492(6) .
N2 C19 1.491(5) .
N2 C20 1.502(5) .
C1 C2 1.569(6) .
C2 C3 1.554(6) .
C2 C5 1.652(6) .
C4 C5 1.560(6) .
C5 C6 1.569(6) .
C7 C8 1.559(6) .
C8 C9 1.566(6) .
C8 C11 1.646(6) .
C10 C11 1.557(6) .
C11 C12 1.564(6) .
