#------------------------------------------------------------------------------
#$Date: 2019-11-24 06:48:51 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/77/4087790.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_4087790
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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                97.8255(18)
_cell_angle_beta                 101.9827(18)
_cell_angle_gamma                105.6509(17)
_cell_formula_units_Z            1
_cell_length_a                   8.8529(4)
_cell_length_b                   10.0267(4)
_cell_length_c                   10.4383(4)
_cell_measurement_reflns_used    10184
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     854.41(6)
_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 0.994
_diffrn_measured_fraction_theta_max 0.992
_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  0.0554
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12733
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         2.734
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0273P)²+0.4614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3508
_reflns_number_total             3883
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00601_si_002.cif
_cod_data_source_block           meso-3
_cod_database_code               4087790
_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.
;
_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:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C10(H10), C14(H14), C17(H17), C11(H11), C4(H4), C18(H18), C12(H12),
 C19(H19), C13(H13), C5(H5), C3(H3), 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'
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
Fe Fe 0.5000 0.0000 0.5000 0.02099(9) Uani 1 2 d S T P
P P 0.36955(4) 0.28839(4) 0.52274(4) 0.01937(10) Uani 1 1 d . . .
N N 0.55314(19) 0.27911(18) 0.88351(15) 0.0376(4) Uani 1 1 d . . .
C16 C 0.15804(19) 0.26931(16) 0.69818(15) 0.0251(3) Uani 1 1 d . . .
H16 H 0.1740 0.1814 0.7101 0.030 Uiso 1 1 calc R . .
C10 C 0.06183(19) 0.16189(17) 0.33482(16) 0.0270(3) Uani 1 1 d . . .
H10 H 0.0207 0.1391 0.4089 0.032 Uiso 1 1 calc R . .
C1 C 0.36245(17) 0.11703(15) 0.56432(14) 0.0190(3) Uani 1 1 d . . .
C15 C 0.23817(17) 0.34664(15) 0.61826(14) 0.0206(3) Uani 1 1 d . . .
C14 C 0.2836(2) 0.26908(18) 0.24590(16) 0.0300(3) Uani 1 1 d . . .
H14 H 0.3947 0.3200 0.2584 0.036 Uiso 1 1 calc R . .
C9 C 0.22653(18) 0.23411(16) 0.35538(15) 0.0223(3) Uani 1 1 d . . .
C17 C 0.05426(19) 0.31977(18) 0.76110(16) 0.0297(3) Uani 1 1 d . . .
H17 H -0.0006 0.2659 0.8152 0.036 Uiso 1 1 calc R . .
C2 C 0.47779(18) 0.09959(17) 0.67602(15) 0.0241(3) Uani 1 1 d . . .
C11 C -0.0425(2) 0.12307(19) 0.20714(18) 0.0335(4) Uani 1 1 d . . .
H11 H -0.1539 0.0731 0.1942 0.040 Uiso 1 1 calc R . .
C4 C 0.3126(2) -0.12304(17) 0.56013(18) 0.0308(4) Uani 1 1 d . . .
H4 H 0.2666 -0.2229 0.5340 0.037 Uiso 1 1 calc R . .
C8 C 0.5287(3) 0.1847(3) 0.9759(2) 0.0536(6) Uani 1 1 d . . .
H8A H 0.4485 0.0941 0.9282 0.080 Uiso 1 1 calc R . .
H8B H 0.6317 0.1691 1.0147 0.080 Uiso 1 1 calc R . .
H8C H 0.4895 0.2271 1.0475 0.080 Uiso 1 1 calc R . .
C18 C 0.0309(2) 0.44846(19) 0.74484(17) 0.0341(4) Uani 1 1 d . . .
H18 H -0.0415 0.4819 0.7863 0.041 Uiso 1 1 calc R . .
C12 C 0.0163(2) 0.1572(2) 0.09909(18) 0.0376(4) Uani 1 1 d . . .
H12 H -0.0550 0.1309 0.0119 0.045 Uiso 1 1 calc R . .
C6 C 0.6089(2) 0.2175(2) 0.77409(16) 0.0329(4) Uani 1 1 d . . .
H6A H 0.6986 0.1814 0.8118 0.039 Uiso 1 1 calc R . .
H6B H 0.6522 0.2923 0.7267 0.039 Uiso 1 1 calc R . .
C19 C 0.1133(3) 0.5277(2) 0.6683(2) 0.0400(4) Uani 1 1 d . . .
H19 H 0.0986 0.6164 0.6579 0.048 Uiso 1 1 calc R . .
C13 C 0.1786(2) 0.2298(2) 0.11768(18) 0.0384(4) Uani 1 1 d . . .
H13 H 0.2187 0.2529 0.0433 0.046 Uiso 1 1 calc R . .
C5 C 0.26143(18) -0.02216(15) 0.49376(16) 0.0234(3) Uani 1 1 d . . .
H5 H 0.1748 -0.0432 0.4157 0.028 Uiso 1 1 calc R . .
C3 C 0.4445(2) -0.04860(19) 0.67231(18) 0.0313(4) Uani 1 1 d . . .
H3 H 0.5011 -0.0904 0.7346 0.038 Uiso 1 1 calc R . .
C20 C 0.2178(2) 0.47806(18) 0.60634(18) 0.0335(4) Uani 1 1 d . . .
H20 H 0.2759 0.5341 0.5554 0.040 Uiso 1 1 calc R . .
C7 C 0.6723(4) 0.4142(3) 0.9536(3) 0.0720(8) Uani 1 1 d . . .
H7A H 0.6882 0.4775 0.8906 0.108 Uiso 1 1 calc R . .
H7B H 0.6333 0.4570 1.0251 0.108 Uiso 1 1 calc R . .
H7C H 0.7755 0.3990 0.9923 0.108 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'
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
C1 Fe C1 180.0 2_656 .
C1 Fe C4 111.13(6) 2_656 .
C1 Fe C4 68.87(6) . .
C1 Fe C4 68.87(6) 2_656 2_656
C1 Fe C4 111.13(6) . 2_656
C2 Fe C1 138.63(6) 2_656 .
C2 Fe C1 41.37(6) 2_656 2_656
C2 Fe C1 138.63(6) . 2_656
C2 Fe C1 41.37(6) . .
C2 Fe C2 180.00(8) 2_656 .
C2 Fe C4 68.85(7) . .
C2 Fe C4 111.15(7) 2_656 .
C2 Fe C4 111.15(7) . 2_656
C2 Fe C4 68.85(7) 2_656 2_656
C2 Fe C5 69.01(6) . .
C2 Fe C5 110.99(6) 2_656 .
C2 Fe C5 69.02(6) 2_656 2_656
C2 Fe C5 110.98(6) . 2_656
C2 Fe C3 40.88(6) 2_656 2_656
C2 Fe C3 139.12(6) 2_656 .
C2 Fe C3 40.89(6) . .
C2 Fe C3 139.11(6) . 2_656
C4 Fe C4 180.0 . 2_656
C5 Fe C1 138.99(6) . 2_656
C5 Fe C1 138.99(6) 2_656 .
C5 Fe C1 41.01(6) . .
C5 Fe C1 41.01(6) 2_656 2_656
C5 Fe C4 139.48(6) 2_656 .
C5 Fe C4 40.52(6) 2_656 2_656
C5 Fe C4 139.48(6) . 2_656
C5 Fe C4 40.52(6) . .
C5 Fe C5 180.0 . 2_656
C3 Fe C1 111.09(6) . 2_656
C3 Fe C1 68.91(6) 2_656 2_656
C3 Fe C1 68.92(6) . .
C3 Fe C1 111.08(6) 2_656 .
C3 Fe C4 40.53(7) . .
C3 Fe C4 139.47(7) 2_656 .
C3 Fe C4 139.47(7) . 2_656
C3 Fe C4 40.53(7) 2_656 2_656
C3 Fe C5 68.25(7) . .
C3 Fe C5 111.75(7) . 2_656
C3 Fe C5 68.25(7) 2_656 2_656
C3 Fe C5 111.75(7) 2_656 .
C3 Fe C3 180.0 . 2_656
C1 P C15 102.28(7) . .
C1 P C9 100.74(7) . .
C15 P C9 98.57(7) . .
C8 N C6 110.74(16) . .
C8 N C7 109.89(18) . .
C7 N C6 109.46(18) . .
C15 C16 H16 119.8 . .
C15 C16 C17 120.44(15) . .
C17 C16 H16 119.8 . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C11 C10 C9 120.72(16) . .
P C1 Fe 122.22(7) . .
C2 C1 Fe 68.96(8) . .
C2 C1 P 122.70(11) . .
C5 C1 Fe 69.44(8) . .
C5 C1 P 130.00(11) . .
C5 C1 C2 107.05(13) . .
C16 C15 P 124.92(11) . .
C16 C15 C20 118.79(14) . .
C20 C15 P 116.29(12) . .
C9 C14 H14 119.8 . .
C9 C14 C13 120.43(17) . .
C13 C14 H14 119.8 . .
C10 C9 P 122.37(12) . .
C14 C9 P 118.90(12) . .
C14 C9 C10 118.71(15) . .
C16 C17 H17 119.9 . .
C18 C17 C16 120.15(16) . .
C18 C17 H17 119.9 . .
C1 C2 Fe 69.66(8) . .
C1 C2 C6 125.06(14) . .
C6 C2 Fe 124.97(11) . .
C3 C2 Fe 69.77(9) . .
C3 C2 C1 107.58(14) . .
C3 C2 C6 127.35(15) . .
C10 C11 H11 120.0 . .
C12 C11 C10 119.94(17) . .
C12 C11 H11 120.0 . .
Fe C4 H4 126.3 . .
C5 C4 Fe 69.68(9) . .
C5 C4 H4 126.0 . .
C3 C4 Fe 69.58(9) . .
C3 C4 H4 126.0 . .
C3 C4 C5 108.07(14) . .
N C8 H8A 109.5 . .
N C8 H8B 109.5 . .
N C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C17 C18 H18 120.1 . .
C19 C18 C17 119.77(15) . .
C19 C18 H18 120.1 . .
C11 C12 H12 119.9 . .
C11 C12 C13 120.15(16) . .
C13 C12 H12 119.9 . .
N C6 C2 112.93(14) . .
N C6 H6A 109.0 . .
N C6 H6B 109.0 . .
C2 C6 H6A 109.0 . .
C2 C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
C18 C19 H19 119.9 . .
C18 C19 C20 120.15(16) . .
C20 C19 H19 119.9 . .
C14 C13 H13 120.0 . .
C12 C13 C14 120.04(17) . .
C12 C13 H13 120.0 . .
Fe C5 H5 126.5 . .
C1 C5 Fe 69.55(8) . .
C1 C5 H5 125.7 . .
C4 C5 Fe 69.80(9) . .
C4 C5 C1 108.61(14) . .
C4 C5 H5 125.7 . .
Fe C3 H3 126.7 . .
C2 C3 Fe 69.35(9) . .
C2 C3 H3 125.7 . .
C4 C3 Fe 69.88(9) . .
C4 C3 C2 108.68(14) . .
C4 C3 H3 125.7 . .
C15 C20 H20 119.7 . .
C19 C20 C15 120.64(17) . .
C19 C20 H20 119.7 . .
N C7 H7A 109.5 . .
N C7 H7B 109.5 . .
N C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe C1 2.0510(13) .
Fe C1 2.0510(13) 2_656
Fe C2 2.0415(15) .
Fe C2 2.0415(15) 2_656
Fe C4 2.0511(16) 2_656
Fe C4 2.0511(16) .
Fe C5 2.0494(14) .
Fe C5 2.0494(14) 2_656
Fe C3 2.0471(16) .
Fe C3 2.0471(16) 2_656
P C1 1.8168(14) .
P C15 1.8377(15) .
P C9 1.8445(15) .
N C8 1.448(3) .
N C6 1.462(2) .
N C7 1.457(3) .
C16 H16 0.9500 .
C16 C15 1.388(2) .
C16 C17 1.394(2) .
C10 H10 0.9500 .
C10 C9 1.398(2) .
C10 C11 1.391(2) .
C1 C2 1.446(2) .
C1 C5 1.436(2) .
C15 C20 1.396(2) .
C14 H14 0.9500 .
C14 C9 1.392(2) .
C14 C13 1.397(2) .
C17 H17 0.9500 .
C17 C18 1.387(2) .
C2 C6 1.493(2) .
C2 C3 1.428(2) .
C11 H11 0.9500 .
C11 C12 1.383(3) .
C4 H4 0.9500 .
C4 C5 1.420(2) .
C4 C3 1.420(3) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C18 H18 0.9500 .
C18 C19 1.380(3) .
C12 H12 0.9500 .
C12 C13 1.384(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C19 H19 0.9500 .
C19 C20 1.389(2) .
C13 H13 0.9500 .
C5 H5 0.9500 .
C3 H3 0.9500 .
C20 H20 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
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
Fe C1 C2 C6 119.12(15)
Fe C1 C2 C3 -59.72(10)
Fe C1 C5 C4 59.05(10)
Fe C2 C6 N 173.37(11)
Fe C2 C3 C4 -58.97(11)
Fe C4 C5 C1 -58.89(10)
Fe C4 C3 C2 58.64(11)
P C1 C2 Fe -115.59(10)
P C1 C2 C6 3.5(2)
P C1 C2 C3 -175.31(11)
P C1 C5 Fe 115.38(12)
P C1 C5 C4 174.42(11)
P C15 C20 C19 176.20(15)
C16 C15 C20 C19 -3.0(3)
C16 C17 C18 C19 -1.3(3)
C10 C11 C12 C13 0.1(3)
C1 P C15 C16 -0.57(15)
C1 P C15 C20 -179.67(12)
C1 P C9 C10 63.84(13)
C1 P C9 C14 -117.68(12)
C1 C2 C6 N 84.93(19)
C1 C2 C3 Fe 59.65(10)
C1 C2 C3 C4 0.68(17)
C15 P C1 Fe -175.24(8)
C15 P C1 C2 -90.96(12)
C15 P C1 C5 95.51(14)
C15 P C9 C10 -40.49(13)
C15 P C9 C14 137.99(12)
C15 C16 C17 C18 -0.4(2)
C9 P C1 Fe 83.42(9)
C9 P C1 C2 167.71(12)
C9 P C1 C5 -5.82(15)
C9 P C15 C16 102.48(14)
C9 P C15 C20 -76.62(13)
C9 C10 C11 C12 -0.7(2)
C9 C14 C13 C12 0.9(3)
C17 C16 C15 P -176.63(12)
C17 C16 C15 C20 2.5(2)
C17 C18 C19 C20 0.8(3)
C2 C1 C5 Fe -58.93(10)
C2 C1 C5 C4 0.11(16)
C11 C10 C9 P 179.79(12)
C11 C10 C9 C14 1.3(2)
C11 C12 C13 C14 -0.2(3)
C8 N C6 C2 73.63(19)
C18 C19 C20 C15 1.4(3)
C6 C2 C3 Fe -119.15(16)
C6 C2 C3 C4 -178.12(15)
C13 C14 C9 P -179.93(12)
C13 C14 C9 C10 -1.4(2)
C5 C1 C2 Fe 59.23(10)
C5 C1 C2 C6 178.35(14)
C5 C1 C2 C3 -0.48(16)
C5 C4 C3 Fe -59.25(11)
C5 C4 C3 C2 -0.61(18)
C3 C2 C6 N -96.46(19)
C3 C4 C5 Fe 59.19(11)
C3 C4 C5 C1 0.30(17)
C7 N C6 C2 -165.05(18)
