#------------------------------------------------------------------------------
#$Date: 2020-09-02 19:55:10 +0300 (Wed, 02 Sep 2020) $
#$Revision: 255805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/75/4317562.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_4317562
loop_
_publ_author_name
'Sam Bradley'
'Kenneth D. Camm'
'Xiaoming Liu'
'Patrick C. McGowan'
'Raheela Mumtaz'
'Karrie A. Oughton'
'Thomas J. Podesta'
'Mark Thornton-Pett'
_publ_contact_author
;
     Patrick McGowan
     School of Chemistry
     University of Leeds
     Leeds LS2 9JT
     UK
;
_publ_contact_author_email       patrickm@chem.leeds.ac.uk
_publ_contact_author_fax         '+44 (0)113 2336565'
_publ_contact_author_phone       '+44 (0)113 2336404'
_publ_section_title
;
 Synthesis and Structural Studies of 1,1'-Bis-Amino-Functionalized
 Ferrocenes, Ferrocene Salts, and Ferrocenium Salts
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              715
_journal_page_last               726
_journal_paper_doi               10.1021/ic010821k
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C28 H38 F6 Fe N2 O4'
_chemical_formula_weight         636.45
_chemical_name_systematic
;
   ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 102.7110(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.39400(10)
_cell_length_b                   12.2973(2)
_cell_length_c                   16.4000(3)
_cell_measurement_temperature    150(2)
_cell_volume                     1454.64(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26747
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.9597
_exptl_absorpt_correction_T_min  0.8856
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.457(16)
_refine_ls_extinction_coef       0.010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5668
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                5241
_reflns_number_total             5668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010821k_5.cif
_cod_data_source_block           kc1
_cod_depositor_comments
;

2020-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C9.33 H12.67 F2 Fe0.33 N0.67 O1.33'
_cod_original_formula_weight         212.15
_cod_original_formula_units_Z            6
_cod_database_code               4317562
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C1 C 0.2963(4) 0.3372(3) 0.22433(19) 0.0286(6) Uani 1 1 d . . .
C2 C 0.2425(4) 0.2364(3) 0.25516(17) 0.0277(5) Uani 1 1 d . . .
H2 H 0.1439 0.1912 0.2274 0.033 Uiso 1 1 calc R . .
C3 C 0.3627(4) 0.2149(3) 0.33528(18) 0.0319(7) Uani 1 1 d . . .
H3 H 0.3585 0.1532 0.3697 0.038 Uiso 1 1 calc R . .
C4 C 0.4890(5) 0.3036(3) 0.3532(2) 0.0343(7) Uani 1 1 d . . .
H4 H 0.5846 0.3115 0.4021 0.041 Uiso 1 1 calc R . .
C5 C 0.4482(4) 0.3777(3) 0.28606(19) 0.0307(7) Uani 1 1 d . . .
H5 H 0.5118 0.4440 0.2825 0.037 Uiso 1 1 calc R . .
C6 C 0.2084(4) 0.3969(3) 0.1458(2) 0.0326(7) Uani 1 1 d . . .
H6 H 0.3056 0.4369 0.1251 0.039 Uiso 1 1 calc R . .
H6 H 0.1195 0.4509 0.1588 0.039 Uiso 1 1 calc R . .
C7 C 0.1076(4) 0.3217(3) 0.0775(2) 0.0330(7) Uani 1 1 d . . .
H7 H 0.1986 0.2728 0.0602 0.040 Uiso 1 1 calc R . .
H7 H 0.0195 0.2761 0.1000 0.040 Uiso 1 1 calc R . .
C9 C -0.1223(5) 0.3065(3) -0.0554(2) 0.0368(7) Uani 1 1 d . . .
H9 H -0.2067 0.2703 -0.0246 0.044 Uiso 1 1 calc R . .
H9 H -0.0468 0.2495 -0.0747 0.044 Uiso 1 1 calc R . .
C10 C -0.2362(5) 0.3658(3) -0.1306(2) 0.0404(8) Uani 1 1 d . . .
H10 H -0.3222 0.4168 -0.1118 0.048 Uiso 1 1 calc R . .
H10 H -0.3113 0.3124 -0.1689 0.048 Uiso 1 1 calc R . .
C11 C -0.1129(5) 0.4287(3) -0.1774(2) 0.0410(8) Uani 1 1 d . . .
H11 H -0.0386 0.3772 -0.2030 0.049 Uiso 1 1 calc R . .
H11 H -0.1909 0.4721 -0.2227 0.049 Uiso 1 1 calc R . .
C12 C 0.0154(5) 0.5037(3) -0.1175(2) 0.0392(8) Uani 1 1 d . . .
H12 H -0.0592 0.5601 -0.0970 0.047 Uiso 1 1 calc R . .
H12 H 0.1002 0.5407 -0.1476 0.047 Uiso 1 1 calc R . .
C14 C 0.1290(4) 0.4421(3) -0.0434(2) 0.0376(8) Uani 1 1 d . . .
H14 H 0.2107 0.3892 -0.0632 0.045 Uiso 1 1 calc R . .
H14 H 0.2082 0.4937 -0.0050 0.045 Uiso 1 1 calc R . .
C15 C 0.7564(4) 0.1430(3) 0.26395(19) 0.0287(6) Uani 1 1 d . . .
C16 C 0.7639(4) 0.2371(3) 0.21362(17) 0.0297(6) Uani 1 1 d . . .
H16 H 0.8494 0.2956 0.2268 0.036 Uiso 1 1 calc R . .
C17 C 0.6198(4) 0.2276(4) 0.13979(17) 0.0325(6) Uani 1 1 d . . .
H17 H 0.5939 0.2782 0.0950 0.039 Uiso 1 1 calc R . .
C18 C 0.5221(4) 0.1294(3) 0.14501(19) 0.0316(7) Uani 1 1 d . . .
H18 H 0.4189 0.1032 0.1046 0.038 Uiso 1 1 calc R . .
C19 C 0.6061(5) 0.0771(3) 0.2215(2) 0.0321(7) Uani 1 1 d . . .
H19 H 0.5684 0.0098 0.2410 0.038 Uiso 1 1 calc R . .
C20 C 0.8947(4) 0.1163(3) 0.34420(19) 0.0319(7) Uani 1 1 d . . .
H20 H 0.9624 0.1832 0.3664 0.038 Uiso 1 1 calc R . .
H20 H 0.9863 0.0634 0.3321 0.038 Uiso 1 1 calc R . .
C21 C 0.8017(4) 0.0691(3) 0.4098(2) 0.0352(7) Uani 1 1 d . . .
H21 H 0.7223 0.1256 0.4271 0.042 Uiso 1 1 calc R . .
H21 H 0.7204 0.0082 0.3849 0.042 Uiso 1 1 calc R . .
C23 C 0.8334(5) -0.0287(3) 0.5421(2) 0.0382(8) Uani 1 1 d . . .
H23 H 0.7625 -0.0901 0.5115 0.046 Uiso 1 1 calc R . .
H23 H 0.7441 0.0222 0.5585 0.046 Uiso 1 1 calc R . .
C24 C 0.9652(5) -0.0712(3) 0.6197(2) 0.0394(8) Uani 1 1 d . . .
H24 H 0.8931 -0.1071 0.6563 0.047 Uiso 1 1 calc R . .
H24 H 1.0483 -0.1262 0.6033 0.047 Uiso 1 1 calc R . .
C25 C 1.0801(5) 0.0191(3) 0.6674(2) 0.0400(8) Uani 1 1 d . . .
H25 H 1.1682 -0.0113 0.7164 0.048 Uiso 1 1 calc R . .
H25 H 0.9984 0.0714 0.6878 0.048 Uiso 1 1 calc R . .
C26 C 1.1874(5) 0.0777(3) 0.6102(2) 0.0397(8) Uani 1 1 d . . .
H26 H 1.2560 0.1400 0.6405 0.048 Uiso 1 1 calc R . .
H26 H 1.2789 0.0272 0.5950 0.048 Uiso 1 1 calc R . .
C27 C 1.0561(5) 0.1188(3) 0.5304(2) 0.0332(7) Uani 1 1 d . . .
H27A H 0.9757 0.1767 0.5449 0.040 Uiso 1 1 calc R . .
H27B H 1.1297 0.1505 0.4926 0.040 Uiso 1 1 calc R . .
C100 C 0.6298(5) 0.6444(3) 0.1190(3) 0.0441(8) Uani 1 1 d . . .
C101 C 0.7102(6) 0.5504(3) 0.0775(3) 0.0483(9) Uani 1 1 d . . .
C200 C 1.3819(5) -0.2058(3) 0.3864(2) 0.0374(8) Uani 1 1 d . . .
C201 C 1.2830(5) -0.1120(3) 0.4191(2) 0.0345(7) Uani 1 1 d . . .
N8 N 0.0034(4) 0.3829(2) 0.00254(16) 0.0277(5) Uani 1 1 d . . .
H8 H -0.0705 0.4344 0.0211 0.033 Uiso 1 1 calc R . .
N22 N 0.9373(4) 0.0285(2) 0.48594(17) 0.0288(6) Uani 1 1 d . . .
H22 H 1.0146 -0.0219 0.4685 0.035 Uiso 1 1 calc R . .
O100 O 0.6186(10) 0.4682(3) 0.0675(4) 0.142(3) Uani 1 1 d . . .
O101 O 0.8481(5) 0.5712(3) 0.0521(2) 0.0663(9) Uani 1 1 d . . .
O200 O 1.1353(4) -0.1375(2) 0.4389(2) 0.0505(7) Uani 1 1 d . . .
O201 O 1.3614(4) -0.0233(2) 0.4260(2) 0.0598(8) Uani 1 1 d . . .
F100 F 0.5126(6) 0.6178(3) 0.1631(3) 0.1105(14) Uani 1 1 d . . .
F101 F 0.5658(4) 0.7241(3) 0.06533(17) 0.0682(7) Uani 1 1 d . . .
F102 F 0.7619(5) 0.6976(3) 0.1753(2) 0.0826(10) Uani 1 1 d . . .
F200 F 1.2666(4) -0.2690(3) 0.33088(16) 0.0660(6) Uani 1 1 d . . .
F201 F 1.4629(4) -0.2727(3) 0.44747(15) 0.0741(8) Uani 1 1 d . . .
F202 F 1.5112(4) -0.1740(2) 0.3463(2) 0.0671(8) Uani 1 1 d . . .
Fe1 Fe 0.51177(5) 0.22801(4) 0.24458(2) 0.02536(15) 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'
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'
Fe Fe 0.3463 0.8444 '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
_geom_angle_publ_flag
C2 C1 C5 106.8(3) . . ?
C2 C1 C6 128.8(3) . . ?
C5 C1 C6 124.3(3) . . ?
C2 C1 Fe1 69.02(17) . . ?
C5 C1 Fe1 69.62(18) . . ?
C6 C1 Fe1 129.2(2) . . ?
C1 C2 C3 108.6(3) . . ?
C1 C2 Fe1 70.16(16) . . ?
C3 C2 Fe1 69.53(15) . . ?
C4 C3 C2 107.0(3) . . ?
C4 C3 Fe1 69.83(18) . . ?
C2 C3 Fe1 69.17(15) . . ?
C5 C4 C3 108.4(3) . . ?
C5 C4 Fe1 70.04(19) . . ?
C3 C4 Fe1 69.45(18) . . ?
C4 C5 C1 109.2(3) . . ?
C4 C5 Fe1 69.75(19) . . ?
C1 C5 Fe1 69.73(18) . . ?
C1 C6 C7 112.7(3) . . ?
N8 C7 C6 112.3(3) . . ?
N8 C9 C10 111.6(3) . . ?
C9 C10 C11 111.5(3) . . ?
C12 C11 C10 109.8(3) . . ?
C11 C12 C14 111.9(3) . . ?
N8 C14 C12 110.4(3) . . ?
C19 C15 C16 107.7(3) . . ?
C19 C15 C20 127.2(3) . . ?
C16 C15 C20 124.9(3) . . ?
C19 C15 Fe1 69.42(18) . . ?
C16 C15 Fe1 69.09(17) . . ?
C20 C15 Fe1 130.4(2) . . ?
C17 C16 C15 107.8(3) . . ?
C17 C16 Fe1 69.81(15) . . ?
C15 C16 Fe1 70.01(16) . . ?
C18 C17 C16 108.2(3) . . ?
C18 C17 Fe1 69.76(17) . . ?
C16 C17 Fe1 69.22(15) . . ?
C19 C18 C17 108.0(3) . . ?
C19 C18 Fe1 69.57(18) . . ?
C17 C18 Fe1 69.71(18) . . ?
C18 C19 C15 108.3(3) . . ?
C18 C19 Fe1 69.70(19) . . ?
C15 C19 Fe1 69.84(18) . . ?
C15 C20 C21 112.0(3) . . ?
N22 C21 C20 113.1(3) . . ?
N22 C23 C24 110.9(3) . . ?
C25 C24 C23 111.5(3) . . ?
C24 C25 C26 109.6(3) . . ?
C27 C26 C25 111.2(3) . . ?
N22 C27 C26 111.3(3) . . ?
F100 C100 F101 111.9(4) . . ?
F100 C100 F102 102.4(4) . . ?
F101 C100 F102 101.1(4) . . ?
F100 C100 C101 115.7(4) . . ?
F101 C100 C101 112.3(3) . . ?
F102 C100 C101 112.1(3) . . ?
O101 C101 O100 128.3(5) . . ?
O101 C101 C100 115.7(4) . . ?
O100 C101 C100 115.7(4) . . ?
F201 C200 F202 107.4(3) . . ?
F201 C200 F200 105.3(3) . . ?
F202 C200 F200 104.6(3) . . ?
F201 C200 C201 112.0(3) . . ?
F202 C200 C201 113.8(3) . . ?
F200 C200 C201 113.1(3) . . ?
O201 C201 O200 128.4(4) . . ?
O201 C201 C200 116.8(3) . . ?
O200 C201 C200 114.7(3) . . ?
C7 N8 C9 109.8(2) . . ?
C7 N8 C14 113.0(2) . . ?
C9 N8 C14 110.5(3) . . ?
C27 N22 C23 111.9(3) . . ?
C27 N22 C21 111.7(2) . . ?
C23 N22 C21 109.1(2) . . ?
C2 Fe1 C16 168.90(12) . . ?
C2 Fe1 C3 41.30(11) . . ?
C16 Fe1 C3 148.69(12) . . ?
C2 Fe1 C18 107.84(13) . . ?
C16 Fe1 C18 68.76(13) . . ?
C3 Fe1 C18 130.85(14) . . ?
C2 Fe1 C19 116.13(14) . . ?
C16 Fe1 C19 68.71(14) . . ?
C3 Fe1 C19 108.84(14) . . ?
C18 Fe1 C19 40.73(13) . . ?
C2 Fe1 C4 68.54(13) . . ?
C16 Fe1 C4 116.49(13) . . ?
C3 Fe1 C4 40.72(14) . . ?
C18 Fe1 C4 170.43(15) . . ?
C19 Fe1 C4 131.93(14) . . ?
C2 Fe1 C17 129.78(11) . . ?
C16 Fe1 C17 40.98(11) . . ?
C3 Fe1 C17 169.41(13) . . ?
C18 Fe1 C17 40.53(16) . . ?
C19 Fe1 C17 68.36(16) . . ?
C4 Fe1 C17 148.50(16) . . ?
C2 Fe1 C5 68.10(14) . . ?
C16 Fe1 C5 108.77(14) . . ?
C3 Fe1 C5 68.28(14) . . ?
C18 Fe1 C5 147.82(13) . . ?
C19 Fe1 C5 170.59(13) . . ?
C4 Fe1 C5 40.21(14) . . ?
C17 Fe1 C5 116.14(16) . . ?
C2 Fe1 C15 148.93(13) . . ?
C16 Fe1 C15 40.90(13) . . ?
C3 Fe1 C15 116.44(13) . . ?
C18 Fe1 C15 68.64(13) . . ?
C19 Fe1 C15 40.74(13) . . ?
C4 Fe1 C15 109.56(13) . . ?
C17 Fe1 C15 68.63(13) . . ?
C5 Fe1 C15 131.59(13) . . ?
C2 Fe1 C1 40.82(14) . . ?
C16 Fe1 C1 129.99(14) . . ?
C3 Fe1 C1 69.25(13) . . ?
C18 Fe1 C1 114.94(12) . . ?
C19 Fe1 C1 147.83(13) . . ?
C4 Fe1 C1 68.58(13) . . ?
C17 Fe1 C1 107.33(14) . . ?
C5 Fe1 C1 40.65(12) . . ?
C15 Fe1 C1 169.69(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.427(5) . ?
C1 C5 1.426(4) . ?
C1 C6 1.501(4) . ?
C1 Fe1 2.054(3) . ?
C2 C3 1.439(4) . ?
C2 Fe1 2.039(3) . ?
C3 C4 1.424(5) . ?
C3 Fe1 2.043(3) . ?
C4 C5 1.410(5) . ?
C4 Fe1 2.049(3) . ?
C5 Fe1 2.052(3) . ?
C6 C7 1.515(5) . ?
C7 N8 1.502(4) . ?
C9 N8 1.504(4) . ?
C9 C10 1.518(5) . ?
C10 C11 1.526(5) . ?
C11 C12 1.519(5) . ?
C12 C14 1.518(5) . ?
C14 N8 1.505(4) . ?
C15 C19 1.427(5) . ?
C15 C16 1.430(5) . ?
C15 C20 1.515(4) . ?
C15 Fe1 2.053(3) . ?
C16 C17 1.431(4) . ?
C16 Fe1 2.040(3) . ?
C17 C18 1.419(6) . ?
C17 Fe1 2.048(3) . ?
C18 C19 1.425(5) . ?
C18 Fe1 2.049(3) . ?
C19 Fe1 2.047(3) . ?
C20 C21 1.515(4) . ?
C21 N22 1.504(4) . ?
C23 N22 1.498(4) . ?
C23 C24 1.516(5) . ?
C24 C25 1.509(5) . ?
C25 C26 1.535(5) . ?
C26 C27 1.534(5) . ?
C27 N22 1.501(4) . ?
C100 F100 1.287(5) . ?
C100 F101 1.333(5) . ?
C100 F102 1.355(5) . ?
C100 C101 1.527(5) . ?
C101 O101 1.211(5) . ?
C101 O100 1.207(6) . ?
C200 F201 1.332(4) . ?
C200 F202 1.333(4) . ?
C200 F200 1.349(4) . ?
C200 C201 1.524(5) . ?
C201 O201 1.229(5) . ?
C201 O200 1.246(4) . ?
