#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:37:10 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195038 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/76/7227696.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_7227696
loop_
_publ_author_name
'Mochida, Tomoyuki'
'Funasako, Yusuke'
'Akasaka, Takahiro'
'Uruichi, Mikio'
'Mori, Hatsumi'
_publ_section_title
;
 Valence engineering of ionic molecular crystals: monovalent--divalent
 phase diagram for biferrocene--tetracyanoquinodimethane salts
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1449
_journal_paper_doi               10.1039/C7CE00134G
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H26 Fe2, 2(C12 H2 F2 N4)'
_chemical_formula_sum            'C48 H30 F4 Fe2 N8'
_chemical_formula_weight         906.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                92.358(12)
_cell_angle_beta                 104.633(12)
_cell_angle_gamma                109.317(11)
_cell_formula_units_Z            1
_cell_length_a                   8.7951(13)
_cell_length_b                   9.1673(13)
_cell_length_c                   13.4002(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.8
_cell_volume                     977.3(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4780
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  0.8548
_exptl_absorpt_correction_T_min  0.8548
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4487
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0314
_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)+(0.0278P)²+0.6341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                3842
_reflns_number_total             4487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00134g2.cif
_cod_data_source_block           4c
_cod_depositor_comments
'Adding full bibliography for 7227693--7227700.cif.'
_cod_original_cell_volume        977.3(2)
_cod_database_code               7227696
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 1.0537(8) 0.6297(6) 0.1319(5) 0.0616(6) Uani 0.454(4) 1 d PU A 1
H12A H 1.0783 0.6016 0.2009 0.092 Uiso 0.454(4) 1 calc PR A 1
H12B H 1.1285 0.7331 0.1316 0.092 Uiso 0.454(4) 1 calc PR A 1
H12C H 1.0681 0.5573 0.0845 0.092 Uiso 0.454(4) 1 calc PR A 1
C13 C 0.7958(7) 0.5403(6) 0.0089(4) 0.0634(13) Uani 0.546(4) 1 d PU A 2
H13A H 0.6845 0.4876 0.0142 0.095 Uiso 0.546(4) 1 calc PR A 2
H13B H 0.8412 0.4649 -0.0100 0.095 Uiso 0.546(4) 1 calc PR A 2
H13C H 0.7917 0.6088 -0.0432 0.095 Uiso 0.546(4) 1 calc PR A 2
C11 C 0.8956(4) 0.6254(3) 0.1026(2) 0.0616(6) Uani 1 1 d U . .
H11A H 0.8240 0.5180 0.0997 0.074 Uiso 0.454(4) 1 calc PR A 1
H11B H 0.8743 0.6499 0.0319 0.074 Uiso 0.454(4) 1 calc PR A 1
H11C H 0.9986 0.6931 0.0906 0.074 Uiso 0.546(4) 1 d PR A 2
H11D H 0.9256 0.5530 0.1476 0.074 Uiso 0.546(4) 1 d PR A 2
C1 C 0.9695(2) 1.0449(2) 0.03157(14) 0.0299(4) Uani 1 1 d . . .
C2 C 1.0629(3) 1.1377(2) 0.12993(15) 0.0370(4) Uani 1 1 d . . .
H2 H 1.1804 1.1553 0.1661 0.044 Uiso 1 1 calc R . .
C3 C 0.9576(3) 1.2023(2) 0.16516(17) 0.0436(5) Uani 1 1 d . . .
H3 H 0.9897 1.2736 0.2296 0.052 Uiso 1 1 calc R . .
C4 C 0.7987(3) 1.1490(3) 0.09000(17) 0.0444(5) Uani 1 1 d . . .
H4 H 0.7018 1.1773 0.0934 0.053 Uiso 1 1 calc R . .
C5 C 0.8048(3) 1.0508(2) 0.00755(15) 0.0381(4) Uani 1 1 d . . .
H5 H 0.7131 0.9988 -0.0555 0.046 Uiso 1 1 calc R . .
C6 C 0.8350(3) 0.7255(2) 0.16304(17) 0.0418(5) Uani 1 1 d . A .
C7 C 0.9298(3) 0.8240(3) 0.25852(17) 0.0485(5) Uani 1 1 d . . .
H7 H 1.0464 0.8392 0.2956 0.058 Uiso 1 1 calc R A .
C8 C 0.8286(4) 0.8952(3) 0.29154(18) 0.0562(6) Uani 1 1 d . A .
H8 H 0.8610 0.9660 0.3562 0.067 Uiso 1 1 calc R . .
C9 C 0.6703(3) 0.8426(3) 0.2166(2) 0.0579(7) Uani 1 1 d . . .
H9 H 0.5731 0.8700 0.2203 0.070 Uiso 1 1 calc R A .
C10 C 0.6747(3) 0.7385(3) 0.13665(19) 0.0494(5) Uani 1 1 d . A .
H10 H 0.5815 0.6830 0.0750 0.059 Uiso 1 1 calc R . .
C14 C 0.4877(2) 0.2555(2) 0.49803(14) 0.0295(4) Uani 1 1 d . . .
C15 C 0.3251(2) 0.2643(2) 0.47238(14) 0.0341(4) Uani 1 1 d . . .
C16 C 0.2741(2) 0.3528(2) 0.53066(14) 0.0342(4) Uani 1 1 d . . .
H16 H 0.1646 0.3520 0.5090 0.041 Uiso 1 1 calc R . .
C17 C 0.3859(2) 0.4467(2) 0.62431(13) 0.0287(4) Uani 1 1 d . . .
C18 C 0.5475(2) 0.4358(2) 0.65082(15) 0.0354(4) Uani 1 1 d . . .
C19 C 0.5980(2) 0.3469(2) 0.59278(15) 0.0358(4) Uani 1 1 d . . .
H19 H 0.7066 0.3456 0.6154 0.043 Uiso 1 1 calc R . .
C20 C 0.5407(2) 0.1650(2) 0.43544(15) 0.0338(4) Uani 1 1 d . . .
C21 C 0.4383(3) 0.0671(2) 0.34125(16) 0.0401(4) Uani 1 1 d . . .
C22 C 0.7043(3) 0.1566(2) 0.46936(16) 0.0384(4) Uani 1 1 d . . .
C23 C 0.3353(2) 0.5418(2) 0.68537(14) 0.0312(4) Uani 1 1 d . . .
C24 C 0.1674(3) 0.5400(2) 0.65657(15) 0.0366(4) Uani 1 1 d . . .
C25 C 0.4347(3) 0.6318(2) 0.78289(16) 0.0382(4) Uani 1 1 d . . .
F1 F 0.21390(17) 0.17974(18) 0.38265(10) 0.0588(4) Uani 1 1 d . . .
F2 F 0.65929(16) 0.52266(19) 0.73967(11) 0.0660(4) Uani 1 1 d . . .
Fe1 Fe 0.85261(4) 0.95991(3) 0.14828(2) 0.03111(8) Uani 1 1 d . A .
N1 N 0.3638(3) -0.0147(3) 0.26459(16) 0.0577(5) Uani 1 1 d . . .
N2 N 0.8338(3) 0.1464(3) 0.49533(16) 0.0560(5) Uani 1 1 d . . .
N3 N 0.0329(2) 0.5397(3) 0.63721(16) 0.0542(5) Uani 1 1 d . . .
N4 N 0.5049(3) 0.7055(3) 0.86271(16) 0.0559(5) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C12 H11C 46.6 . .
H12A C12 H11C 141.4 . .
H12B C12 H11C 66.5 . .
H12C C12 H11C 107.7 . .
C11 C12 H11D 44.8 . .
H12A C12 H11D 71.4 . .
H12B C12 H11D 146.0 . .
H12C C12 H11D 101.5 . .
H11C C12 H11D 91.4 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C11 C13 117.2(4) . .
C12 C11 C6 121.6(3) . .
C13 C11 C6 120.8(3) . .
C12 C11 H11A 106.9 . .
C13 C11 H11A 60.1 . .
C6 C11 H11A 106.9 . .
C12 C11 H11B 106.9 . .
C13 C11 H11B 46.7 . .
C6 C11 H11B 106.9 . .
H11A C11 H11B 106.7 . .
C12 C11 H11C 47.1 . .
C13 C11 H11C 106.9 . .
C6 C11 H11C 107.1 . .
H11A C11 H11C 145.2 . .
H11B C11 H11C 69.6 . .
C12 C11 H11D 59.8 . .
C13 C11 H11D 107.3 . .
C6 C11 H11D 107.2 . .
H11A C11 H11D 55.5 . .
H11B C11 H11D 145.0 . .
H11C C11 H11D 106.8 . .
C2 C1 C5 107.70(16) . .
C2 C1 C1 126.1(2) . 2_775
C5 C1 C1 126.1(2) . 2_775
C2 C1 Fe1 69.47(10) . .
C5 C1 Fe1 69.34(11) . .
C1 C1 Fe1 125.03(17) 2_775 .
C3 C2 C1 108.16(18) . .
C3 C2 Fe1 69.64(12) . .
C1 C2 Fe1 71.01(11) . .
C3 C2 H2 125.9 . .
C1 C2 H2 125.9 . .
Fe1 C2 H2 125.9 . .
C4 C3 C2 108.05(18) . .
C4 C3 Fe1 69.85(12) . .
C2 C3 Fe1 70.92(11) . .
C4 C3 H3 126.0 . .
C2 C3 H3 126.0 . .
Fe1 C3 H3 126.0 . .
C3 C4 C5 108.39(18) . .
C3 C4 Fe1 70.36(12) . .
C5 C4 Fe1 70.82(11) . .
C3 C4 H4 125.8 . .
C5 C4 H4 125.8 . .
Fe1 C4 H4 125.8 . .
C4 C5 C1 107.69(18) . .
C4 C5 Fe1 69.38(12) . .
C1 C5 Fe1 71.23(11) . .
C4 C5 H5 126.1 . .
C1 C5 H5 126.1 . .
Fe1 C5 H5 126.1 . .
C10 C6 C7 107.3(2) . .
C10 C6 C11 126.9(2) . .
C7 C6 C11 125.8(2) . .
C10 C6 Fe1 68.90(12) . .
C7 C6 Fe1 69.36(12) . .
C11 C6 Fe1 127.37(15) . .
C8 C7 C6 108.8(2) . .
C8 C7 Fe1 69.38(13) . .
C6 C7 Fe1 71.35(12) . .
C8 C7 H7 125.6 . .
C6 C7 H7 125.6 . .
Fe1 C7 H7 125.6 . .
C9 C8 C7 107.7(2) . .
C9 C8 Fe1 69.59(13) . .
C7 C8 Fe1 71.26(12) . .
C9 C8 H8 126.1 . .
C7 C8 H8 126.1 . .
Fe1 C8 H8 126.1 . .
C8 C9 C10 108.1(2) . .
C8 C9 Fe1 70.53(13) . .
C10 C9 Fe1 70.82(13) . .
C8 C9 H9 125.9 . .
C10 C9 H9 125.9 . .
Fe1 C9 H9 125.9 . .
C6 C10 C9 108.1(2) . .
C6 C10 Fe1 71.95(12) . .
C9 C10 Fe1 69.08(13) . .
C6 C10 H10 126.0 . .
C9 C10 H10 126.0 . .
Fe1 C10 H10 126.0 . .
C15 C14 C20 124.06(17) . .
C15 C14 C19 114.62(16) . .
C20 C14 C19 121.32(17) . .
C16 C15 F1 118.03(17) . .
C16 C15 C14 124.55(17) . .
F1 C15 C14 117.42(16) . .
C15 C16 C17 120.66(17) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C18 C17 C23 123.86(17) . .
C18 C17 C16 114.78(16) . .
C23 C17 C16 121.36(17) . .
C19 C18 F2 118.21(17) . .
C19 C18 C17 124.49(18) . .
F2 C18 C17 117.30(16) . .
C18 C19 C14 120.88(18) . .
C18 C19 H19 119.6 . .
C14 C19 H19 119.6 . .
C14 C20 C21 125.31(18) . .
C14 C20 C22 120.51(17) . .
C21 C20 C22 113.99(17) . .
N1 C21 C20 175.7(2) . .
N2 C22 C20 178.4(2) . .
C17 C23 C25 125.28(17) . .
C17 C23 C24 120.59(17) . .
C25 C23 C24 113.79(16) . .
N3 C24 C23 177.5(2) . .
N4 C25 C23 175.2(2) . .
C9 Fe1 C8 39.88(11) . .
C9 Fe1 C4 108.76(10) . .
C8 Fe1 C4 123.38(9) . .
C9 Fe1 C3 123.23(9) . .
C8 Fe1 C3 108.20(9) . .
C4 Fe1 C3 39.80(9) . .
C9 Fe1 C10 40.11(10) . .
C8 Fe1 C10 66.91(10) . .
C4 Fe1 C10 124.63(10) . .
C3 Fe1 C10 159.37(9) . .
C9 Fe1 C7 66.27(11) . .
C8 Fe1 C7 39.36(10) . .
C4 Fe1 C7 158.64(9) . .
C3 Fe1 C7 123.85(9) . .
C10 Fe1 C7 66.05(10) . .
C9 Fe1 C5 124.40(10) . .
C8 Fe1 C5 159.18(9) . .
C4 Fe1 C5 39.80(8) . .
C3 Fe1 C5 66.79(9) . .
C10 Fe1 C5 110.17(9) . .
C7 Fe1 C5 160.30(8) . .
C9 Fe1 C2 158.34(9) . .
C8 Fe1 C2 123.44(10) . .
C4 Fe1 C2 66.44(9) . .
C3 Fe1 C2 39.44(8) . .
C10 Fe1 C2 160.12(8) . .
C7 Fe1 C2 109.96(9) . .
C5 Fe1 C2 66.52(8) . .
C9 Fe1 C6 66.40(9) . .
C8 Fe1 C6 66.34(9) . .
C4 Fe1 C6 160.07(9) . .
C3 Fe1 C6 159.33(9) . .
C10 Fe1 C6 39.15(9) . .
C7 Fe1 C6 39.29(9) . .
C5 Fe1 C6 125.45(8) . .
C2 Fe1 C6 125.32(8) . .
C9 Fe1 C1 160.16(10) . .
C8 Fe1 C1 159.18(10) . .
C4 Fe1 C1 66.30(8) . .
C3 Fe1 C1 66.30(7) . .
C10 Fe1 C1 125.36(8) . .
C7 Fe1 C1 125.43(9) . .
C5 Fe1 C1 39.43(7) . .
C2 Fe1 C1 39.52(7) . .
C6 Fe1 C1 111.21(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C12 C11 1.332(7) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C12 H11C 0.9783 .
C12 H11D 1.1895 .
C13 C11 1.365(5) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C11 C6 1.504(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 H11C 0.9700 .
C11 H11D 0.9700 .
C1 C2 1.426(3) .
C1 C5 1.422(3) .
C1 C1 1.464(3) 2_775
C1 Fe1 2.1194(17) .
C2 C3 1.411(3) .
C2 Fe1 2.099(2) .
C2 H2 0.9800 .
C3 C4 1.415(3) .
C3 Fe1 2.082(2) .
C3 H3 0.9800 .
C4 C5 1.419(3) .
C4 Fe1 2.075(2) .
C4 H4 0.9800 .
C5 Fe1 2.094(2) .
C5 H5 0.9800 .
C6 C10 1.410(3) .
C6 C7 1.419(3) .
C6 Fe1 2.124(2) .
C7 C8 1.405(3) .
C7 Fe1 2.098(2) .
C7 H7 0.9800 .
C8 C9 1.410(4) .
C8 Fe1 2.073(2) .
C8 H8 0.9800 .
C9 C10 1.421(3) .
C9 Fe1 2.061(2) .
C9 H9 0.9800 .
C10 Fe1 2.084(2) .
C10 H10 0.9800 .
C14 C15 1.415(3) .
C14 C20 1.416(2) .
C14 C19 1.417(3) .
C15 C16 1.354(3) .
C15 F1 1.353(2) .
C16 C17 1.418(3) .
C16 H16 0.9300 .
C17 C18 1.413(3) .
C17 C23 1.418(2) .
C18 C19 1.352(3) .
C18 F2 1.353(2) .
C19 H19 0.9300 .
C20 C21 1.417(3) .
C20 C22 1.424(3) .
C21 N1 1.148(3) .
C22 N2 1.141(3) .
C23 C25 1.418(3) .
C23 C24 1.423(3) .
C24 N3 1.144(3) .
C25 N4 1.146(3) .
