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#$Date: 2019-11-24 10:09:53 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237585 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/84/4088453.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_4088453
loop_
_publ_author_name
'Tondreau, Aaron M.'
'Scott, Brian L.'
'Boncella, James M.'
_publ_section_title
;
 A Tertiary Carbon--Iron Bond as an FeICl Synthon and the Reductive
 Alkylation of Diphosphine-Supported Iron(II) Chloride Complexes to
 Low-Valent Iron
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              1643
_journal_paper_doi               10.1021/acs.organomet.6b00108
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C29 H31 Cl F0.5 Fe N2 Si'
_chemical_formula_weight         536.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                83.672(3)
_cell_angle_beta                 74.459(3)
_cell_angle_gamma                85.048(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7299(12)
_cell_length_b                   11.4681(14)
_cell_length_c                   12.7531(15)
_cell_measurement_reflns_used    9192
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.33
_cell_volume                     1360.3(3)
_computing_cell_refinement       'APEX2 V.2014.7-1 (Bruker AXS, 2014)'
_computing_data_collection       'APEX2 V.2014.7-1 (Bruker AXS, 2014)'
_computing_data_reduction        'SAINT, v. 8.34A (Bruker AXS, 2013)'
_computing_molecular_graphics    'SHELXTL, v. 2014/7, (Bruker AXS, 2014)'
_computing_publication_material  'SHELXTL, v. 2014/7, (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Quest with CMOS detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Bruker Triumph curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_min         2.176
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 2014/3 (Bruker AXS, 2013)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       plate
_exptl_crystal_F_000             561
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.279
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0445
_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)+(0.0930P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4663
_reflns_number_total             5464
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00108_si_002.cif
_cod_data_source_block           dq0037
_cod_original_formula_sum        'C29 H31 Cl F0.50 Fe N2 Si'
_cod_database_code               4088453
_shelx_shelxl_version_number     2014/7
_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_min   0.869
_shelx_estimated_absorpt_t_max   0.972
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
Fe1 Fe 0.91152(3) 0.67541(3) 0.27642(2) 0.01404(13) Uani 1 1 d . . .
Cl1 Cl 1.11786(6) 0.58479(5) 0.31080(4) 0.02049(15) Uani 1 1 d . . .
Si1 Si 0.97497(6) 0.93938(5) 0.29667(5) 0.01829(17) Uani 1 1 d . . .
F1 F 0.5470(4) 0.7259(3) 0.9674(3) 0.0362(7) Uani 0.5 1 d . . P
N1 N 0.9514(2) 0.66744(16) 0.10483(15) 0.0171(4) Uani 1 1 d . . .
N2 N 0.7692(2) 0.53766(16) 0.33572(15) 0.0173(4) Uani 1 1 d . . .
C1 C 0.8233(2) 0.83804(18) 0.33069(17) 0.0134(4) Uani 1 1 d . . .
C2 C 0.7099(2) 0.86720(19) 0.27099(18) 0.0161(4) Uani 1 1 d . . .
C3 C 0.5824(2) 0.8083(2) 0.30277(18) 0.0194(5) Uani 1 1 d . . .
H3 H 0.5667 0.7538 0.3659 0.023 Uiso 1 1 calc R U .
C4 C 0.4790(3) 0.8268(2) 0.2457(2) 0.0276(6) Uani 1 1 d . . .
H4 H 0.3952 0.7839 0.2690 0.033 Uiso 1 1 calc R U .
C5 C 0.4970(3) 0.9080(3) 0.1541(2) 0.0334(7) Uani 1 1 d . . .
H5 H 0.4258 0.9215 0.1150 0.040 Uiso 1 1 calc R U .
C6 C 0.6200(3) 0.9684(2) 0.1214(2) 0.0318(6) Uani 1 1 d . . .
H6 H 0.6335 1.0242 0.0592 0.038 Uiso 1 1 calc R U .
C7 C 0.7242(3) 0.9488(2) 0.17809(19) 0.0230(5) Uani 1 1 d . . .
H7 H 0.8079 0.9917 0.1536 0.028 Uiso 1 1 calc R U .
C8 C 0.7659(2) 0.82428(18) 0.45351(17) 0.0136(4) Uani 1 1 d . . .
C9 C 0.8242(2) 0.74076(19) 0.52004(18) 0.0165(5) Uani 1 1 d . . .
H9 H 0.8996 0.6875 0.4870 0.020 Uiso 1 1 calc R U .
C10 C 0.7751(2) 0.7331(2) 0.63341(19) 0.0191(5) Uani 1 1 d . . .
H10 H 0.8171 0.6750 0.6763 0.023 Uiso 1 1 calc R U .
C11 C 0.6655(2) 0.8095(2) 0.68407(18) 0.0192(5) Uani 1 1 d . . .
H11 H 0.6319 0.8044 0.7615 0.023 Uiso 1 1 calc R U .
C12 C 0.6060(2) 0.8934(2) 0.62004(18) 0.0179(5) Uani 1 1 d . . .
H12 H 0.5308 0.9464 0.6537 0.021 Uiso 1 1 calc R U .
C13 C 0.6551(2) 0.90070(19) 0.50693(18) 0.0154(4) Uani 1 1 d . . .
H13 H 0.6125 0.9590 0.4646 0.018 Uiso 1 1 calc R U .
C14 C 1.0931(3) 0.9306(3) 0.1540(2) 0.0310(6) Uani 1 1 d . . .
H14A H 1.1594 0.9938 0.1366 0.046 Uiso 1 1 calc R U .
H14B H 1.0340 0.9390 0.1020 0.046 Uiso 1 1 calc R U .
H14C H 1.1473 0.8544 0.1492 0.046 Uiso 1 1 calc R U .
C15 C 0.9050(3) 1.0957(2) 0.3154(2) 0.0286(6) Uani 1 1 d . . .
H15A H 0.8381 1.0996 0.3878 0.043 Uiso 1 1 calc R U .
H15B H 0.8556 1.1241 0.2590 0.043 Uiso 1 1 calc R U .
H15C H 0.9848 1.1449 0.3090 0.043 Uiso 1 1 calc R U .
C16 C 1.0930(2) 0.8978(2) 0.3898(2) 0.0247(5) Uani 1 1 d . . .
H16A H 1.1706 0.9516 0.3727 0.037 Uiso 1 1 calc R U .
H16B H 1.1335 0.8172 0.3800 0.037 Uiso 1 1 calc R U .
H16C H 1.0372 0.9026 0.4657 0.037 Uiso 1 1 calc R U .
C17 C 0.8595(3) 0.7065(2) 0.04544(19) 0.0214(5) Uani 1 1 d . . .
H17 H 0.7672 0.7372 0.0817 0.026 Uiso 1 1 calc R U .
C18 C 0.8940(3) 0.7037(2) -0.0671(2) 0.0258(5) Uani 1 1 d . . .
H18 H 0.8265 0.7326 -0.1068 0.031 Uiso 1 1 calc R U .
C19 C 1.0274(3) 0.6586(2) -0.1207(2) 0.0280(6) Uani 1 1 d . . .
H19 H 1.0525 0.6546 -0.1976 0.034 Uiso 1 1 calc R U .
C20 C 1.1229(3) 0.6195(2) -0.0606(2) 0.0282(6) Uani 1 1 d . . .
H20 H 1.2158 0.5888 -0.0954 0.034 Uiso 1 1 calc R U .
C21 C 1.0819(3) 0.6255(2) 0.0511(2) 0.0225(5) Uani 1 1 d . . .
H21 H 1.1488 0.5987 0.0920 0.027 Uiso 1 1 calc R U .
C22 C 0.6615(3) 0.5228(2) 0.29260(19) 0.0222(5) Uani 1 1 d . . .
H22 H 0.6487 0.5756 0.2327 0.027 Uiso 1 1 calc R U .
C23 C 0.5685(3) 0.4346(3) 0.3308(2) 0.0344(7) Uani 1 1 d . . .
H23 H 0.4926 0.4277 0.2984 0.041 Uiso 1 1 calc R U .
C24 C 0.5870(4) 0.3565(3) 0.4169(2) 0.0397(7) Uani 1 1 d . . .
H24 H 0.5252 0.2941 0.4441 0.048 Uiso 1 1 calc R U .
C25 C 0.6968(3) 0.3709(2) 0.4623(2) 0.0341(6) Uani 1 1 d . . .
H25 H 0.7117 0.3187 0.5220 0.041 Uiso 1 1 calc R U .
C26 C 0.7851(3) 0.4620(2) 0.42019(19) 0.0230(5) Uani 1 1 d . . .
H26 H 0.8604 0.4715 0.4524 0.028 Uiso 1 1 calc R U .
C28 C 0.5250(3) 0.6166(2) 0.9843(2) 0.0287(6) Uani 1 1 d . . .
C29 C 0.5908(3) 0.5445(2) 0.9033(2) 0.0291(6) Uani 1 1 d . . .
H29 H 0.6534 0.5757 0.8375 0.035 Uiso 1 1 calc R U .
C30 C 0.5652(3) 0.4271(2) 0.9187(2) 0.0278(6) Uani 1 1 d . . .
H30 H 0.6089 0.3765 0.8633 0.033 Uiso 1 1 calc R U .
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'
Cl Cl 0.1484 0.1585 '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'
Si Si 0.0817 0.0704 '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'
F F 0.0171 0.0103 '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_3
C1 Fe1 N1 114.25(8) .
C1 Fe1 N2 112.90(8) .
N1 Fe1 N2 100.50(7) .
C1 Fe1 Cl1 123.66(6) .
N1 Fe1 Cl1 102.02(5) .
N2 Fe1 Cl1 100.27(5) .
C16 Si1 C15 107.80(12) .
C16 Si1 C14 105.92(12) .
C15 Si1 C14 109.32(12) .
C16 Si1 C1 109.81(10) .
C15 Si1 C1 110.71(11) .
C14 Si1 C1 113.05(11) .
C17 N1 C21 117.5(2) .
C17 N1 Fe1 125.05(16) .
C21 N1 Fe1 117.35(16) .
C22 N2 C26 117.3(2) .
C22 N2 Fe1 122.74(16) .
C26 N2 Fe1 119.96(16) .
C2 C1 C8 113.71(17) .
C2 C1 Si1 116.59(15) .
C8 C1 Si1 107.79(14) .
C2 C1 Fe1 102.54(14) .
C8 C1 Fe1 109.14(14) .
Si1 C1 Fe1 106.55(10) .
C3 C2 C7 115.5(2) .
C3 C2 C1 120.53(19) .
C7 C2 C1 123.9(2) .
C4 C3 C2 122.5(2) .
C3 C4 C5 120.3(3) .
C6 C5 C4 118.8(2) .
C5 C6 C7 120.8(2) .
C6 C7 C2 122.1(2) .
C9 C8 C13 116.47(19) .
C9 C8 C1 122.56(19) .
C13 C8 C1 120.88(19) .
C10 C9 C8 122.0(2) .
C11 C10 C9 120.4(2) .
C12 C11 C10 118.9(2) .
C11 C12 C13 120.6(2) .
C12 C13 C8 121.8(2) .
N1 C17 C18 122.4(2) .
C19 C18 C17 119.4(2) .
C20 C19 C18 118.6(2) .
C19 C20 C21 119.0(2) .
N1 C21 C20 123.1(2) .
N2 C22 C23 123.2(2) .
C22 C23 C24 119.0(3) .
C25 C24 C23 118.6(2) .
C24 C25 C26 119.1(2) .
N2 C26 C25 122.8(2) .
F1 C28 C29 118.6(3) .
F1 C28 C30 120.1(3) 2_667
C29 C28 C30 121.3(3) 2_667
C30 C29 C28 119.5(2) .
C29 C30 C28 119.2(2) 2_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C1 2.094(2) .
Fe1 N1 2.1285(19) .
Fe1 N2 2.1302(19) .
Fe1 Cl1 2.3053(6) .
Si1 C16 1.863(3) .
Si1 C15 1.879(3) .
Si1 C14 1.881(3) .
Si1 C1 1.886(2) .
F1 C28 1.275(4) .
N1 C17 1.339(3) .
N1 C21 1.347(3) .
N2 C22 1.338(3) .
N2 C26 1.341(3) .
C1 C2 1.496(3) .
C1 C8 1.511(3) .
C2 C3 1.405(3) .
C2 C7 1.410(3) .
C3 C4 1.381(3) .
C4 C5 1.393(4) .
C5 C6 1.378(4) .
C6 C7 1.385(4) .
C8 C9 1.394(3) .
C8 C13 1.404(3) .
C9 C10 1.391(3) .
C10 C11 1.385(3) .
C11 C12 1.383(3) .
C12 C13 1.388(3) .
C17 C18 1.386(3) .
C18 C19 1.381(4) .
C19 C20 1.374(4) .
C20 C21 1.380(3) .
C22 C23 1.375(4) .
C23 C24 1.378(4) .
C24 C25 1.374(4) .
C25 C26 1.379(4) .
C28 C29 1.380(4) .
C28 C30 1.381(4) 2_667
C29 C30 1.374(4) .
C30 C28 1.381(4) 2_667
