#------------------------------------------------------------------------------
#$Date: 2019-11-24 06:48:51 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/77/4087789.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_4087789
loop_
_publ_author_name
'Allouch, Fatima'
'Dwadnia, Nejib'
'Vologdin, Nikolay V.'
'Svyaschenko, Yurii V.'
'Cattey, Hélène'
'Penouilh, Marie-José'
'Roger, Julien'
'Naoufal, Daoud'
'Ben Salem, Ridha'
'Pirio, Nadine'
'Hierso, Jean-Cyrille'
_publ_section_title
;
 Converging and Diverging Synthetic Strategies to Tetradentate
 (N,N′)-Diaminomethyl,(P,P′)-Ferrocenyl Ligands: Influence
 of tert-Butyl Groups on Ferrocene Backbone Conformation
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5015
_journal_paper_doi               10.1021/acs.organomet.5b00601
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C40 H42 Fe N2 P2'
_chemical_formula_sum            'C40 H42 Fe N2 P2'
_chemical_formula_weight         668.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 103.958(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1230(7)
_cell_length_b                   7.6042(3)
_cell_length_c                   24.7744(9)
_cell_measurement_reflns_used    11147
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     3313.4(2)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius,1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa APEX II'
_diffrn_measurement_method       'φ and ω scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5466
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.316
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0114P)²+10.2248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3358
_reflns_number_total             3730
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00601_si_002.cif
_cod_data_source_block           rac-3
_cod_database_code               4087789
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with grease'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.89815(10) 0.0738(3) 0.19125(8) 0.0156(4) Uani 1 1 d . . .
C2 C 0.90430(10) 0.2210(3) 0.22916(8) 0.0164(4) Uani 1 1 d . . .
C3 C 0.91355(11) 0.1515(3) 0.28381(8) 0.0189(4) Uani 1 1 d . . .
C4 C 0.91331(11) -0.0355(3) 0.28067(8) 0.0189(4) Uani 1 1 d . . .
H4 H 0.9183 -0.1143 0.3111 0.023 Uiso 1 1 calc R . .
C5 C 0.90426(10) -0.0835(3) 0.22409(8) 0.0170(4) Uani 1 1 d . . .
H5 H 0.9025 -0.2003 0.2102 0.020 Uiso 1 1 calc R . .
C6 C 0.89987(11) 0.4135(3) 0.21430(9) 0.0201(4) Uani 1 1 d . . .
H6A H 0.9359 0.4783 0.2441 0.024 Uiso 1 1 calc R . .
H6B H 0.9173 0.4285 0.1796 0.024 Uiso 1 1 calc R . .
C7 C 0.79868(13) 0.4983(3) 0.25764(10) 0.0304(5) Uani 1 1 d . . .
H7A H 0.8376 0.5536 0.2871 0.046 Uiso 1 1 calc R . .
H7B H 0.7513 0.5656 0.2518 0.046 Uiso 1 1 calc R . .
H7C H 0.7898 0.3777 0.2685 0.046 Uiso 1 1 calc R . .
C8 C 0.76767(12) 0.4139(3) 0.16169(9) 0.0272(5) Uani 1 1 d . . .
H8A H 0.7860 0.4132 0.1276 0.041 Uiso 1 1 calc R . .
H8B H 0.7587 0.2928 0.1720 0.041 Uiso 1 1 calc R . .
H8C H 0.7201 0.4807 0.1554 0.041 Uiso 1 1 calc R . .
C9 C 0.95237(11) -0.0641(3) 0.09990(8) 0.0202(4) Uani 1 1 d . . .
C10 C 0.94706(12) -0.2448(3) 0.10813(9) 0.0249(4) Uani 1 1 d . . .
H10 H 0.9060 -0.2901 0.1216 0.030 Uiso 1 1 calc R . .
C11 C 1.00123(14) -0.3590(3) 0.09680(10) 0.0328(5) Uani 1 1 d . . .
H11 H 0.9978 -0.4816 0.1032 0.039 Uiso 1 1 calc R . .
C12 C 1.06066(15) -0.2930(4) 0.07592(10) 0.0371(6) Uani 1 1 d . . .
H12 H 1.0983 -0.3705 0.0687 0.045 Uiso 1 1 calc R . .
C13 C 1.06482(13) -0.1160(4) 0.06574(9) 0.0333(5) Uani 1 1 d . . .
H13 H 1.1045 -0.0720 0.0505 0.040 Uiso 1 1 calc R . .
C14 C 1.01131(12) -0.0013(3) 0.07769(8) 0.0254(5) Uani 1 1 d . . .
H14 H 1.0148 0.1209 0.0707 0.031 Uiso 1 1 calc R . .
C15 C 0.79523(11) -0.0047(3) 0.08609(8) 0.0193(4) Uani 1 1 d . . .
C16 C 0.75563(12) -0.1154(3) 0.11395(9) 0.0243(4) Uani 1 1 d . . .
H16 H 0.7754 -0.1391 0.1524 0.029 Uiso 1 1 calc R . .
C17 C 0.68730(12) -0.1916(3) 0.08583(9) 0.0268(5) Uani 1 1 d . . .
H17 H 0.6608 -0.2670 0.1053 0.032 Uiso 1 1 calc R . .
C18 C 0.65755(12) -0.1587(3) 0.02993(9) 0.0256(5) Uani 1 1 d . . .
H18 H 0.6112 -0.2122 0.0109 0.031 Uiso 1 1 calc R . .
C19 C 0.69597(12) -0.0472(3) 0.00198(9) 0.0280(5) Uani 1 1 d . . .
H19 H 0.6757 -0.0233 -0.0364 0.034 Uiso 1 1 calc R . .
C20 C 0.76411(12) 0.0297(3) 0.02981(8) 0.0231(4) Uani 1 1 d . . .
H20 H 0.7898 0.1067 0.0103 0.028 Uiso 1 1 calc R . .
Fe Fe 1.0000 0.06727(5) 0.2500 0.01429(10) Uani 1 2 d S T P
N N 0.82435(10) 0.4953(2) 0.20628(8) 0.0232(4) Uani 1 1 d . . .
P P 0.88731(3) 0.10099(7) 0.11666(2) 0.01810(12) Uani 1 1 d . . .
H3 H 0.9216(13) 0.221(3) 0.3188(10) 0.020(6) Uiso 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'
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'
P P 0.1023 0.0942 '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
C2 C1 Fe 69.16(10) . .
C2 C1 P 122.86(14) . .
C5 C1 C2 107.04(16) . .
C5 C1 Fe 69.24(11) . .
C5 C1 P 130.08(15) . .
P C1 Fe 125.39(10) . .
C1 C2 C6 126.96(18) . .
C1 C2 Fe 69.57(10) . .
C3 C2 C1 107.61(17) . .
C3 C2 C6 125.41(18) . .
C3 C2 Fe 69.58(11) . .
C6 C2 Fe 127.38(13) . .
C2 C3 Fe 69.75(11) . .
C2 C3 H3 126.2(14) . .
C4 C3 C2 108.68(18) . .
C4 C3 Fe 70.01(11) . .
C4 C3 H3 125.1(14) . .
Fe C3 H3 123.8(13) . .
C3 C4 H4 126.0 . .
C3 C4 Fe 69.41(11) . .
C5 C4 C3 108.00(18) . .
C5 C4 H4 126.0 . .
C5 C4 Fe 69.48(11) . .
Fe C4 H4 126.7 . .
C1 C5 H5 125.7 . .
C1 C5 Fe 69.83(11) . .
C4 C5 C1 108.67(17) . .
C4 C5 H5 125.7 . .
C4 C5 Fe 70.08(11) . .
Fe C5 H5 126.0 . .
C2 C6 H6A 108.3 . .
C2 C6 H6B 108.3 . .
H6A C6 H6B 107.4 . .
N C6 C2 115.87(17) . .
N C6 H6A 108.3 . .
N C6 H6B 108.3 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N C7 H7A 109.5 . .
N C7 H7B 109.5 . .
N C7 H7C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N C8 H8A 109.5 . .
N C8 H8B 109.5 . .
N C8 H8C 109.5 . .
C10 C9 C14 118.7(2) . .
C10 C9 P 124.68(16) . .
C14 C9 P 116.66(17) . .
C9 C10 H10 119.7 . .
C11 C10 C9 120.6(2) . .
C11 C10 H10 119.7 . .
C10 C11 H11 120.1 . .
C10 C11 C12 119.8(2) . .
C12 C11 H11 120.1 . .
C11 C12 H12 120.0 . .
C13 C12 C11 120.1(2) . .
C13 C12 H12 120.0 . .
C12 C13 H13 119.9 . .
C12 C13 C14 120.2(2) . .
C14 C13 H13 119.9 . .
C9 C14 H14 119.7 . .
C13 C14 C9 120.6(2) . .
C13 C14 H14 119.7 . .
C16 C15 C20 118.41(19) . .
C16 C15 P 125.72(15) . .
C20 C15 P 115.86(16) . .
C15 C16 H16 119.8 . .
C17 C16 C15 120.40(19) . .
C17 C16 H16 119.8 . .
C16 C17 H17 119.6 . .
C18 C17 C16 120.7(2) . .
C18 C17 H17 119.6 . .
C17 C18 H18 120.3 . .
C17 C18 C19 119.4(2) . .
C19 C18 H18 120.3 . .
C18 C19 H19 119.9 . .
C18 C19 C20 120.24(19) . .
C20 C19 H19 119.9 . .
C15 C20 H20 119.6 . .
C19 C20 C15 120.8(2) . .
C19 C20 H20 119.6 . .
C1 Fe C1 177.24(11) 2_755 .
C1 Fe C4 68.64(7) . .
C1 Fe C4 68.63(7) 2_755 2_755
C1 Fe C4 112.50(7) 2_755 .
C1 Fe C4 112.49(7) . 2_755
C2 Fe C1 41.28(7) . .
C2 Fe C1 136.39(8) . 2_755
C2 Fe C1 41.28(7) 2_755 2_755
C2 Fe C1 136.39(8) 2_755 .
C2 Fe C2 110.52(11) . 2_755
C2 Fe C4 142.94(8) 2_755 .
C2 Fe C4 68.59(8) 2_755 2_755
C2 Fe C4 68.59(8) . .
C2 Fe C4 142.94(8) . 2_755
C3 Fe C1 68.76(8) . .
C3 Fe C1 68.76(8) 2_755 2_755
C3 Fe C1 110.32(8) . 2_755
C3 Fe C1 110.31(8) 2_755 .
C3 Fe C2 113.72(8) 2_755 .
C3 Fe C2 40.68(8) 2_755 2_755
C3 Fe C2 40.67(8) . .
C3 Fe C2 113.72(8) . 2_755
C3 Fe C3 143.57(12) . 2_755
C3 Fe C4 40.58(8) . .
C3 Fe C4 175.52(9) 2_755 .
C3 Fe C4 175.52(9) . 2_755
C3 Fe C4 40.58(8) 2_755 2_755
C3 Fe C5 136.04(8) . 2_755
C3 Fe C5 68.28(8) 2_755 2_755
C3 Fe C5 136.04(8) 2_755 .
C3 Fe C5 68.28(8) . .
C4 Fe C4 135.35(12) . 2_755
C5 Fe C1 40.93(7) . .
C5 Fe C1 40.93(7) 2_755 2_755
C5 Fe C1 141.48(8) 2_755 .
C5 Fe C1 141.49(8) . 2_755
C5 Fe C2 68.87(8) . .
C5 Fe C2 176.44(8) 2_755 .
C5 Fe C2 176.44(8) . 2_755
C5 Fe C2 68.87(8) 2_755 2_755
C5 Fe C4 40.44(8) . .
C5 Fe C4 40.44(8) 2_755 2_755
C5 Fe C4 109.63(8) 2_755 .
C5 Fe C4 109.63(8) . 2_755
C5 Fe C5 111.96(11) . 2_755
C7 N C6 111.77(17) . .
C8 N C6 112.72(17) . .
C8 N C7 110.77(17) . .
C1 P C9 103.51(9) . .
C1 P C15 103.46(9) . .
C9 P C15 100.14(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.448(3) .
C1 C5 1.436(3) .
C1 Fe 2.0572(18) .
C1 P 1.8222(19) .
C2 C3 1.425(3) .
C2 C6 1.507(3) .
C2 Fe 2.0516(19) .
C3 C4 1.424(3) .
C3 Fe 2.0494(19) .
C3 H3 0.99(2) .
C4 H4 0.9500 .
C4 C5 1.419(3) .
C4 Fe 2.0573(19) .
C5 H5 0.9500 .
C5 Fe 2.0494(19) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 N 1.473(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C7 N 1.457(3) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C8 N 1.453(3) .
C9 C10 1.396(3) .
C9 C14 1.398(3) .
C9 P 1.837(2) .
C10 H10 0.9500 .
C10 C11 1.389(3) .
C11 H11 0.9500 .
C11 C12 1.396(4) .
C12 H12 0.9500 .
C12 C13 1.375(4) .
C13 H13 0.9500 .
C13 C14 1.388(3) .
C14 H14 0.9500 .
C15 C16 1.392(3) .
C15 C20 1.397(3) .
C15 P 1.842(2) .
C16 H16 0.9500 .
C16 C17 1.392(3) .
C17 H17 0.9500 .
C17 C18 1.382(3) .
C18 H18 0.9500 .
C18 C19 1.384(3) .
C19 H19 0.9500 .
C19 C20 1.390(3) .
C20 H20 0.9500 .
Fe C1 2.0572(18) 2_755
Fe C2 2.0517(19) 2_755
Fe C3 2.0495(19) 2_755
Fe C4 2.0573(19) 2_755
Fe C5 2.0494(19) 2_755
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 C2 C3 C4 0.0(2)
C1 C2 C3 Fe 59.40(13)
C1 C2 C6 N 94.2(2)
C2 C1 C5 C4 0.5(2)
C2 C1 C5 Fe -59.05(12)
C2 C1 P C9 136.75(16)
C2 C1 P C15 -119.14(16)
C2 C3 C4 C5 0.3(2)
C2 C3 C4 Fe 59.21(13)
C2 C6 N C7 65.2(2)
C2 C6 N C8 -60.4(2)
C3 C2 C6 N -84.1(2)
C3 C4 C5 C1 -0.4(2)
C3 C4 C5 Fe 58.91(13)
C5 C1 C2 C3 -0.3(2)
C5 C1 C2 C6 -178.86(18)
C5 C1 C2 Fe 59.11(13)
C5 C1 P C9 -41.5(2)
C5 C1 P C15 62.65(19)
C6 C2 C3 C4 178.62(18)
C6 C2 C3 Fe -122.01(19)
C9 C10 C11 C12 -1.3(3)
C10 C9 C14 C13 -2.0(3)
C10 C9 P C1 60.11(19)
C10 C9 P C15 -46.52(19)
C10 C11 C12 C13 -1.1(4)
C11 C12 C13 C14 1.9(4)
C12 C13 C14 C9 -0.3(3)
C14 C9 C10 C11 2.8(3)
C14 C9 P C1 -119.44(16)
C14 C9 P C15 133.92(16)
C15 C16 C17 C18 -0.1(3)
C16 C15 C20 C19 -1.2(3)
C16 C15 P C1 -14.4(2)
C16 C15 P C9 92.3(2)
C16 C17 C18 C19 -0.7(3)
C17 C18 C19 C20 0.5(3)
C18 C19 C20 C15 0.5(3)
C20 C15 C16 C17 1.0(3)
C20 C15 P C1 166.43(16)
C20 C15 P C9 -86.90(17)
Fe C1 C2 C3 -59.41(13)
Fe C1 C2 C6 122.03(19)
Fe C1 C5 C4 59.52(13)
Fe C1 P C9 50.23(14)
Fe C1 P C15 154.34(12)
Fe C2 C3 C4 -59.37(14)
Fe C2 C6 N -174.34(14)
Fe C3 C4 C5 -58.95(13)
Fe C4 C5 C1 -59.36(13)
P C1 C2 C3 -178.87(13)
P C1 C2 C6 2.6(3)
P C1 C2 Fe -119.46(14)
P C1 C5 C4 178.89(14)
P C1 C5 Fe 119.37(16)
P C9 C10 C11 -176.72(16)
P C9 C14 C13 177.58(17)
P C15 C16 C17 -178.16(17)
P C15 C20 C19 178.04(17)
