#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/74/4117428.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_4117428
loop_
_publ_author_name
'Adriana Iordache'
'Mircea Oltean'
'Anne Milet'
'Fabrice Thomas'
'Benoît Baptiste'
'Eric Saint-Aman'
'Christophe Bucher'
_publ_section_title
;
 Redox Control of Rotary Motions in Ferrocene-Based Elemental Ball
 Bearings
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2653
_journal_page_last               2671
_journal_paper_doi               10.1021/ja209766e
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         '(C34 H32 Fe N4), 2(C2 N), 2(I), 0.5(O)'
_chemical_formula_sum            'C38 H32 Fe I2 N6 O0.5'
_chemical_formula_weight         890.37
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             2011-09-23
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                90
_cell_angle_beta                 95.22(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.21(2)
_cell_length_b                   13.120(1)
_cell_length_c                   11.85(1)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     3903(5)
_computing_cell_refinement       'Bruker Enraf Nonius kappa CCD'
_computing_data_collection       'Bruker Enraf Nonius kappa CCD'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker Enraf Nonius kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      0.00000
_diffrn_orient_matrix_UB_12      0.00000
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.00000
_diffrn_orient_matrix_UB_31      0.00000
_diffrn_orient_matrix_UB_32      0.00000
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.12247
_diffrn_reflns_av_sigmaI/netI    0.070
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14585
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.003
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       needle
_exptl_crystal_F_000             1752.00
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.11
_refine_diff_density_min         -0.85
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.904
_refine_ls_goodness_of_fit_ref   1.904
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0702
_refine_ls_shift/su_max          0.0240
_refine_ls_shift/su_mean         0.0095
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00040|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0771
_refine_ls_wR_factor_ref         0.0771
_reflns_number_gt                2325
_reflns_number_total             4430
_reflns_threshold_expression     I>2.00σ(I)
_cod_data_source_file            ja209766e_si_004.cif
_cod_data_source_block           Adriana
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_original_formula_sum        'C38 H32 Fe I2 N6 O0.50 '
_cod_database_code               4117428
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   +y,1/2-z'
'   -x,   -y,   -z'
'   +x,   -y,1/2+z'
'1/2+x,1/2+y,   +z'
1/2-x,1/2+y,1/2-z
'1/2-x,1/2-y,   -z'
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_refinement_flags
_atom_site_adp_type
_atom_site_calc_flag
I(1) 0.15380(3) 0.20337(4) 0.45124(5) 0.0575(2) 1.000 . Uani d
Fe(1) 0.0000 0.1311(1) 0.7500 0.0160(3) 1.000 ST Uani d
O(1) 0.0000 -0.280(4) 0.7500 0.22(2) 0.500 S Uiso d
N(8) 0.1618(2) -0.1119(4) 0.5959(5) 0.021(2) 1.000 . Uani d
N(17) 0.2164(3) -0.5019(5) 0.2104(5) 0.036(2) 1.000 . Uani d
N(20a) 0.0667(8) -0.589(1) 0.602(2) 0.098(6) 0.600 . Uiso d
N(20b) 0.070(1) -0.434(3) 0.478(3) 0.11(1) 0.400 . Uiso d
C(1) 0.0733(3) 0.0633(5) 0.7480(6) 0.020(2) 1.000 . Uani d
C(2) 0.0776(3) 0.1706(5) 0.7330(6) 0.025(2) 1.000 . Uani d
C(3) 0.0596(3) 0.2217(5) 0.8269(6) 0.029(2) 1.000 . Uani d
C(4) 0.0429(3) 0.1460(6) 0.9025(6) 0.029(2) 1.000 . Uani d
C(5) 0.0516(3) 0.0491(5) 0.8568(5) 0.022(2) 1.000 . Uani d
C(6) 0.0879(3) -0.0173(5) 0.6690(6) 0.025(2) 1.000 . Uani d
C(7) 0.1472(3) -0.0324(5) 0.6758(6) 0.026(2) 1.000 . Uani d
C(9) 0.1583(3) -0.2097(6) 0.6262(6) 0.031(2) 1.000 . Uani d
C(10) 0.1691(3) -0.2878(5) 0.5543(6) 0.033(2) 1.000 . Uani d
C(11) 0.1846(3) -0.2646(5) 0.4450(5) 0.018(2) 1.000 . Uani d
C(12) 0.1886(3) -0.1617(5) 0.4188(6) 0.024(2) 1.000 . Uani d
C(13) 0.1766(3) -0.0875(5) 0.4941(6) 0.023(2) 1.000 . Uani d
C(14) 0.1958(3) -0.3459(5) 0.3639(6) 0.021(2) 1.000 . Uani d
C(15) 0.1960(4) -0.4502(6) 0.3945(6) 0.037(2) 1.000 . Uani d
C(16) 0.2062(4) -0.5223(6) 0.3170(8) 0.044(3) 1.000 . Uani d
C(18) 0.2171(4) -0.4042(7) 0.1817(6) 0.040(2) 1.000 . Uani d
C(19) 0.2073(4) -0.3257(6) 0.2550(6) 0.034(2) 1.000 . Uani d
C(21a) 0.066(1) -0.523(2) 0.503(2) 0.104(8) 0.600 . Uiso d
C(21b) 0.062(2) -0.469(3) 0.573(4) 0.12(1) 0.400 . Uiso d
C(22a) 0.065(1) -0.483(2) 0.400(3) 0.13(1) 0.600 . Uiso d
C(22b) 0.062(5) -0.520(8) 0.69(1) 0.38(2) 0.400 . Uiso d
H(1) 0.0906 0.2028 0.6692 0.030 1.000 . Uiso c
H(2) 0.0588 0.2934 0.8379 0.035 1.000 . Uiso c
H(3) 0.0283 0.1589 0.9723 0.035 1.000 . Uiso c
H(4) 0.0446 -0.0144 0.8908 0.026 1.000 . Uiso c
H(5) 0.0715 -0.0795 0.6878 0.030 1.000 . Uiso c
H(6) 0.0756 0.0017 0.5938 0.030 1.000 . Uiso c
H(7) 0.1595 -0.0523 0.7507 0.032 1.000 . Uiso c
H(8) 0.1636 0.0300 0.6579 0.032 1.000 . Uiso c
H(9) 0.1481 -0.2256 0.6994 0.037 1.000 . Uiso c
H(10) 0.1663 -0.3568 0.5777 0.040 1.000 . Uiso c
H(11) 0.1998 -0.1424 0.3475 0.028 1.000 . Uiso c
H(12) 0.1790 -0.0178 0.4734 0.027 1.000 . Uiso c
H(13) 0.1891 -0.4698 0.4689 0.044 1.000 . Uiso c
H(14) 0.2062 -0.5917 0.3400 0.053 1.000 . Uiso c
H(15) 0.2248 -0.3872 0.1069 0.048 1.000 . Uiso c
H(16) 0.2084 -0.2571 0.2298 0.041 1.000 . Uiso c
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 152 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 156 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Fe 0 4 0.301 0.845
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
I 0 8 -0.726 1.812
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N 0 24 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0 2 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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
C1 FE1 C1 128.6(4) . 2_556 yes
C1 FE1 C2 40.6(3) . . yes
C1 FE1 C2 168.0(3) . 2_556 yes
C1 FE1 C3 68.5(3) . . yes
C1 FE1 C3 149.9(3) . 2_556 yes
C1 FE1 C4 69.2(3) . . yes
C1 FE1 C4 116.0(3) . 2_556 yes
C1 FE1 C5 41.7(3) . . yes
C1 FE1 C5 106.8(3) . 2_556 yes
C1 FE1 C2 168.0(3) 2_556 . yes
C1 FE1 C2 40.6(3) 2_556 2_556 yes
C1 FE1 C3 149.9(3) 2_556 . yes
C1 FE1 C3 68.5(3) 2_556 2_556 yes
C1 FE1 C4 116.0(3) 2_556 . yes
C1 FE1 C4 69.2(3) 2_556 2_556 yes
C1 FE1 C5 106.8(3) 2_556 . yes
C1 FE1 C5 41.7(3) 2_556 2_556 yes
C2 FE1 C2 150.8(4) . 2_556 yes
C2 FE1 C3 40.1(3) . . yes
C2 FE1 C3 118.3(3) . 2_556 yes
C2 FE1 C4 68.1(3) . . yes
C2 FE1 C4 108.9(3) . 2_556 yes
C2 FE1 C5 68.5(3) . . yes
C2 FE1 C5 129.3(3) . 2_556 yes
C2 FE1 C3 118.3(3) 2_556 . yes
C2 FE1 C3 40.1(3) 2_556 2_556 yes
C2 FE1 C4 108.9(3) 2_556 . yes
C2 FE1 C4 68.1(3) 2_556 2_556 yes
C2 FE1 C5 129.3(3) 2_556 . yes
C2 FE1 C5 68.5(3) 2_556 2_556 yes
C3 FE1 C3 109.6(4) . 2_556 yes
C3 FE1 C4 40.8(3) . . yes
C3 FE1 C4 130.3(3) . 2_556 yes
C3 FE1 C5 68.4(3) . . yes
C3 FE1 C5 167.8(3) . 2_556 yes
C3 FE1 C4 130.3(3) 2_556 . yes
C3 FE1 C4 40.8(3) 2_556 2_556 yes
C3 FE1 C5 167.8(3) 2_556 . yes
C3 FE1 C5 68.4(3) 2_556 2_556 yes
C4 FE1 C4 169.0(4) . 2_556 yes
C4 FE1 C5 40.5(3) . . yes
C4 FE1 C5 149.6(3) . 2_556 yes
C4 FE1 C5 149.6(3) 2_556 . yes
C4 FE1 C5 40.5(3) 2_556 2_556 yes
C5 FE1 C5 116.3(4) . 2_556 yes
C7 N8 C9 118.6(6) . . yes
C7 N8 C13 121.1(6) . . yes
C9 N8 C13 120.2(6) . . yes
C16 N17 C18 116.3(6) . . yes
FE1 C1 C2 69.6(4) . . yes
FE1 C1 C5 68.6(4) . . yes
FE1 C1 C6 126.4(5) . . yes
FE1 C1 H5 114.8 . . no
FE1 C1 H6 106.6 . . no
C2 C1 C5 106.0(6) . . yes
C2 C1 C6 126.9(7) . . yes
C2 C1 H5 151.5 . . no
C2 C1 H6 106.0 . . no
C5 C1 C6 127.1(6) . . yes
C5 C1 H5 101.4 . . no
C5 C1 H6 143.1 . . no
FE1 C2 C1 69.8(4) . . yes
FE1 C2 C3 70.4(4) . . yes
FE1 C2 H1 126.3 . . no
C1 C2 C3 109.8(7) . . yes
C1 C2 H1 125.1 . . no
C3 C2 H1 125.1 . . no
FE1 C3 C2 69.5(4) . . yes
FE1 C3 C4 68.4(4) . . yes
FE1 C3 H2 127.4 . . no
C2 C3 C4 107.4(6) . . yes
C2 C3 H2 126.3 . . no
C4 C3 H2 126.3 . . no
FE1 C4 C3 70.8(4) . . yes
FE1 C4 C5 70.1(4) . . yes
FE1 C4 H3 125.1 . . no
C3 C4 C5 108.8(6) . . yes
C3 C4 H3 125.6 . . no
C5 C4 H3 125.6 . . no
FE1 C5 C1 69.7(4) . . yes
FE1 C5 C4 69.5(4) . . yes
FE1 C5 H4 126.4 . . no
C1 C5 C4 108.0(6) . . yes
C1 C5 H4 126.0 . . no
C4 C5 H4 126.0 . . no
C1 C6 C7 111.4(6) . . yes
C1 C6 H5 109.0 . . no
C1 C6 H6 109.0 . . no
C7 C6 H5 109.0 . . no
C7 C6 H6 109.0 . . no
H5 C6 H6 109.5 . . no
N8 C7 C6 111.3(6) . . yes
N8 C7 H7 109.0 . . no
N8 C7 H8 109.0 . . no
C6 C7 H7 109.0 . . no
C6 C7 H8 109.0 . . no
H7 C7 H8 109.4 . . no
N8 C9 C10 121.8(6) . . yes
N8 C9 H9 119.1 . . no
C10 C9 H9 119.1 . . no
C9 C10 C11 119.4(6) . . yes
C9 C10 H10 120.3 . . no
C11 C10 H10 120.3 . . no
C10 C11 C12 116.3(6) . . yes
C10 C11 C14 121.5(6) . . yes
C12 C11 C14 122.1(6) . . yes
C11 C12 C13 121.3(7) . . yes
C11 C12 H11 119.4 . . no
C13 C12 H11 119.4 . . no
N8 C13 C12 120.9(6) . . yes
N8 C13 H12 119.5 . . no
C12 C13 H12 119.5 . . no
C11 C14 C15 121.7(6) . . yes
C11 C14 C19 122.7(6) . . yes
C15 C14 C19 115.5(7) . . yes
C14 C15 C16 119.7(7) . . yes
C14 C15 H13 120.2 . . no
C16 C15 H13 120.1 . . no
N17 C16 C15 124.3(7) . . yes
N17 C16 H14 117.9 . . no
C15 C16 H14 117.9 . . no
N17 C18 C19 123.4(7) . . yes
N17 C18 H15 118.3 . . no
C19 C18 H15 118.3 . . no
C14 C19 C18 120.8(7) . . yes
C14 C19 H16 119.6 . . no
C18 C19 H16 119.6 . . no
N20a C21a C22a 167(3) . . yes
N20b C21b C22b 171(6) . . yes
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
FE1 C1 2.052(8) . yes
FE1 C1 2.052(8) 2_556 yes
FE1 C2 2.050(9) . yes
FE1 C2 2.050(9) 2_556 yes
FE1 C3 2.062(8) . yes
FE1 C3 2.062(8) 2_556 yes
FE1 C4 2.029(7) . yes
FE1 C4 2.029(7) 2_556 yes
FE1 C5 2.037(7) . yes
FE1 C5 2.037(7) 2_556 yes
N8 C7 1.477(9) . yes
N8 C9 1.337(9) . yes
N8 C13 1.335(9) . yes
N17 C16 1.34(1) . yes
N17 C18 1.33(1) . yes
N20a C21a 1.46(3) . yes
N20b C21b 1.25(5) . yes
C1 C2 1.423(9) . yes
C1 C5 1.457(9) . yes
C1 C6 1.482(9) . yes
C2 C3 1.41(1) . yes
C2 H1 0.95 . no
C3 C4 1.43(1) . yes
C3 H2 0.95 . no
C4 C5 1.41(1) . yes
C4 H3 0.95 . no
C5 H4 0.95 . no
C6 C7 1.50(1) . yes
C6 H5 0.95 . no
C6 H6 0.95 . no
C7 H7 0.95 . no
C7 H8 0.95 . no
C9 C10 1.38(1) . yes
C9 H9 0.95 . no
C10 C11 1.42(1) . yes
C10 H10 0.95 . no
C11 C12 1.391(9) . yes
C11 C14 1.480(9) . yes
C12 C13 1.37(1) . yes
C12 H11 0.95 . no
C13 H12 0.95 . no
C14 C15 1.42(1) . yes
C14 C19 1.37(1) . yes
C15 C16 1.36(1) . yes
C15 H13 0.95 . no
C16 H14 0.95 . no
C18 C19 1.38(1) . yes
C18 H15 0.95 . no
C19 H16 0.95 . no
C21a C22a 1.33(4) . yes
C21b C22b 1.5(1) . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N17 C10 3.470(9) 4_544 no
N20a C22a 3.44(4) 3_546 no
N20a N20b 3.50(4) 3_546 no
N20a C2 3.51(2) 1_545 no
N20b C10 3.22(3) . no
N20b C3 3.31(3) 4_554 no
N20b C15 3.43(3) . no
N20b C22b 3.5(1) 4_544 no
N20b C21a 3.49(4) 3_546 no
N20b C21b 3.56(5) 3_546 no
C2 C12 3.40(1) 4 no
C3 C11 3.38(1) 4 no
C3 C12 3.42(1) 4 no
C3 C22a 3.54(3) 4 no
C4 C13 3.53(1) 4 no
C5 C13 3.45(1) 4 no
C9 C19 3.58(1) 7_546 no
C11 C11 3.45(2) 7_546 no
C11 C12 3.58(1) 7_546 no
C13 C15 3.39(1) 7_546 no
C13 C14 3.60(1) 7_546 no
C15 C22a 3.35(3) . no
C21a C21b 3.28(5) 3_546 no
C21a C21a 3.38(5) 3_546 no
C21a C22a 3.58(4) 3_546 no
C21b C22a 3.31(6) 3_546 no
C21b C21b 3.54(9) 3_546 no
C22a C22b 2.5(1) 4_544 no
C22a C22b 3.3(1) 3_546 no
C22b C22b 3.6(3) 2_556 no
