#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:42:38 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179420 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/17/4331701.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_4331701
loop_
_publ_author_name
'Xiaojie Wang'
'Zhenbo Mo'
'Jie Xiao'
'Liang Deng'
_publ_section_title
;
 Monomeric Bis(anilido)iron(II) Complexes with N-Heterocyclic Carbene
 Ligation: Synthesis, Characterization, and Redox Reactivity toward Aryl
 Halides
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              59
_journal_page_last               65
_journal_paper_doi               10.1021/ic301894e
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C46 H76 Fe N6'
_chemical_formula_weight         768.98
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 126.6050(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.435(3)
_cell_length_b                   11.5817(13)
_cell_length_c                   18.907(4)
_cell_measurement_reflns_used    6203
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.13
_cell_measurement_theta_min      2.19
_cell_volume                     4471.1(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20930
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.9289
_exptl_absorpt_correction_T_min  0.8801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         6527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0712P)²+4.4826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                5379
_reflns_number_total             6527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301894e_si_002_5.cif
_cod_data_source_block           5
_cod_original_cell_volume        4471.1(11)
_cod_database_code               4331701
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Fe1 Fe 0.0000 0.98338(3) 0.2500 0.01974(9) Uani 1 2 d S
N1 N 0.10223(7) 1.13732(12) 0.42638(9) 0.0259(3) Uani 1 1 d .
N2 N 0.09528(7) 1.20114(12) 0.31448(9) 0.0254(3) Uani 1 1 d .
N3 N 0.05201(7) 0.90831(13) 0.21587(11) 0.0323(3) Uani 1 1 d .
H1N H 0.0825 0.9569 0.2413 0.039 Uiso 1 1 d R
C1 C 0.07356(7) 1.11398(13) 0.33982(10) 0.0233(3) Uani 1 1 d .
C2 C 0.13996(8) 1.23826(16) 0.45385(12) 0.0317(4) Uani 1 1 d .
C3 C 0.13597(8) 1.27769(15) 0.38352(12) 0.0306(3) Uani 1 1 d .
C4 C 0.17437(11) 1.2948(2) 0.54248(14) 0.0456(5) Uani 1 1 d .
H4A H 0.2016 1.3584 0.5468 0.068 Uiso 1 1 calc R
H4B H 0.2021 1.2379 0.5887 0.068 Uiso 1 1 calc R
H4C H 0.1419 1.3249 0.5498 0.068 Uiso 1 1 calc R
C5 C 0.16760(10) 1.38334(18) 0.37841(16) 0.0427(5) Uani 1 1 d .
H5A H 0.1976 1.4168 0.4374 0.064 Uiso 1 1 calc R
H5B H 0.1338 1.4400 0.3391 0.064 Uiso 1 1 calc R
H5C H 0.1921 1.3623 0.3554 0.064 Uiso 1 1 calc R
C6 C 0.09657(9) 1.05805(17) 0.48260(11) 0.0309(3) Uani 1 1 d .
H6 H 0.0691 0.9913 0.4448 0.037 Uiso 1 1 calc R
C7 C 0.16384(11) 1.0095(2) 0.55632(15) 0.0513(6) Uani 1 1 d .
H7A H 0.1845 0.9761 0.5308 0.077 Uiso 1 1 calc R
H7B H 0.1587 0.9496 0.5883 0.077 Uiso 1 1 calc R
H7C H 0.1915 1.0718 0.5970 0.077 Uiso 1 1 calc R
C8 C 0.06204(11) 1.1120(2) 0.51792(14) 0.0439(5) Uani 1 1 d .
H8A H 0.0881 1.1769 0.5566 0.066 Uiso 1 1 calc R
H8B H 0.0570 1.0541 0.5513 0.066 Uiso 1 1 calc R
H8C H 0.0188 1.1399 0.4686 0.066 Uiso 1 1 calc R
C9 C 0.07504(9) 1.21008(15) 0.22342(11) 0.0295(3) Uani 1 1 d .
H9 H 0.0470 1.1414 0.1906 0.035 Uiso 1 1 calc R
C10 C 0.13408(11) 1.2038(2) 0.22068(14) 0.0429(5) Uani 1 1 d .
H10A H 0.1561 1.2789 0.2371 0.064 Uiso 1 1 calc R
H10B H 0.1191 1.1836 0.1610 0.064 Uiso 1 1 calc R
H10C H 0.1647 1.1448 0.2622 0.064 Uiso 1 1 calc R
C11 C 0.03319(11) 1.31663(17) 0.17685(14) 0.0413(4) Uani 1 1 d .
H11A H -0.0055 1.3142 0.1766 0.062 Uiso 1 1 calc R
H11B H 0.0192 1.3182 0.1161 0.062 Uiso 1 1 calc R
H11C H 0.0588 1.3861 0.2079 0.062 Uiso 1 1 calc R
C12 C 0.07182(8) 0.80277(14) 0.20495(10) 0.0236(3) Uani 1 1 d .
C13 C 0.02618(9) 0.71486(15) 0.15360(11) 0.0296(3) Uani 1 1 d .
C14 C 0.04707(12) 0.61255(17) 0.13902(15) 0.0432(5) Uani 1 1 d .
H14 H 0.0156 0.5547 0.1030 0.052 Uiso 1 1 calc R
C15 C 0.11156(13) 0.59286(18) 0.17506(18) 0.0518(6) Uani 1 1 d .
H15 H 0.1246 0.5224 0.1639 0.062 Uiso 1 1 calc R
C16 C 0.15793(11) 0.67719(19) 0.22819(15) 0.0453(5) Uani 1 1 d .
H16 H 0.2028 0.6631 0.2541 0.054 Uiso 1 1 calc R
C17 C 0.13953(8) 0.78222(16) 0.24405(12) 0.0317(4) Uani 1 1 d .
C18 C 0.19072(9) 0.8717(2) 0.30203(14) 0.0446(5) Uani 1 1 d .
H18 H 0.1735 0.9395 0.2785 0.053 Uiso 1 1 d R
C19 C 0.20626(14) 0.8708(4) 0.39395(18) 0.0777(10) Uani 1 1 d .
H19A H 0.1655 0.8783 0.3882 0.117 Uiso 1 1 calc R
H19B H 0.2353 0.9356 0.4286 0.117 Uiso 1 1 calc R
H19C H 0.2278 0.7980 0.4237 0.117 Uiso 1 1 calc R
C20 C 0.25396(11) 0.8622(3) 0.30978(17) 0.0603(7) Uani 1 1 d .
H20A H 0.2766 0.7903 0.3402 0.090 Uiso 1 1 calc R
H20B H 0.2824 0.9281 0.3434 0.090 Uiso 1 1 calc R
H20C H 0.2434 0.8622 0.2508 0.090 Uiso 1 1 calc R
C21 C -0.04661(9) 0.73135(16) 0.10972(12) 0.0333(4) Uani 1 1 d .
H21 H -0.0520 0.8029 0.1345 0.040 Uiso 1 1 calc R
C22 C -0.08273(12) 0.7493(2) 0.01074(14) 0.0507(5) Uani 1 1 d .
H22A H -0.0634 0.8148 0.0009 0.076 Uiso 1 1 calc R
H22B H -0.1291 0.7650 -0.0170 0.076 Uiso 1 1 calc R
H22C H -0.0788 0.6795 -0.0151 0.076 Uiso 1 1 calc R
C23 C -0.07724(11) 0.63160(19) 0.12527(15) 0.0424(4) Uani 1 1 d .
H23A H -0.0731 0.5607 0.1007 0.064 Uiso 1 1 calc R
H23B H -0.1237 0.6480 0.0965 0.064 Uiso 1 1 calc R
H23C H -0.0547 0.6217 0.1887 0.064 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'
N N 0.0061 0.0033 '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
N3 Fe1 N3 128.04(9) 2 .
N3 Fe1 C1 97.28(6) 2 2
N3 Fe1 C1 118.22(6) . 2
N3 Fe1 C1 118.23(6) 2 .
N3 Fe1 C1 97.28(6) . .
C1 Fe1 C1 93.61(8) 2 .
C1 N1 C2 111.60(14) . .
C1 N1 C6 121.96(14) . .
C2 N1 C6 126.28(14) . .
C1 N2 C3 111.73(14) . .
C1 N2 C9 121.82(13) . .
C3 N2 C9 126.43(14) . .
C12 N3 Fe1 143.90(12) . .
C12 N3 H1N 112.5 . .
Fe1 N3 H1N 95.1 . .
N1 C1 N2 103.62(13) . .
N1 C1 Fe1 131.28(11) . .
N2 C1 Fe1 124.74(11) . .
C3 C2 N1 106.51(14) . .
C3 C2 C4 127.07(17) . .
N1 C2 C4 126.31(17) . .
C2 C3 N2 106.51(15) . .
C2 C3 C5 127.67(17) . .
N2 C3 C5 125.81(17) . .
C2 C4 H4A 109.5 . .
C2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N1 C6 C8 113.02(16) . .
N1 C6 C7 110.39(15) . .
C8 C6 C7 112.11(17) . .
N1 C6 H6 107.0 . .
C8 C6 H6 107.0 . .
C7 C6 H6 107.0 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N2 C9 C11 111.64(15) . .
N2 C9 C10 111.58(15) . .
C11 C9 C10 112.34(15) . .
N2 C9 H9 107.0 . .
C11 C9 H9 107.0 . .
C10 C9 H9 107.0 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N3 C12 C13 121.18(14) . .
N3 C12 C17 120.18(15) . .
C13 C12 C17 118.62(15) . .
C14 C13 C12 119.81(17) . .
C14 C13 C21 118.84(17) . .
C12 C13 C21 121.29(15) . .
C15 C14 C13 121.9(2) . .
C15 C14 H14 119.0 . .
C13 C14 H14 119.0 . .
C14 C15 C16 119.35(19) . .
C14 C15 H15 120.3 . .
C16 C15 H15 120.3 . .
C15 C16 C17 121.10(18) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C16 C17 C12 119.15(18) . .
C16 C17 C18 120.00(17) . .
C12 C17 C18 120.85(17) . .
C17 C18 C20 115.1(2) . .
C17 C18 C19 110.27(19) . .
C20 C18 C19 110.17(19) . .
C17 C18 H18 107.0 . .
C20 C18 H18 106.9 . .
C19 C18 H18 107.0 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C23 C21 C13 113.38(16) . .
C23 C21 C22 109.71(17) . .
C13 C21 C22 109.37(16) . .
C23 C21 H21 108.1 . .
C13 C21 H21 108.1 . .
C22 C21 H21 108.1 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 C23 H23A 109.5 . .
C21 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C21 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 N3 1.9848(14) 2
Fe1 N3 1.9849(14) .
Fe1 C1 2.2098(16) 2
Fe1 C1 2.2098(16) .
N1 C1 1.364(2) .
N1 C2 1.401(2) .
N1 C6 1.475(2) .
N2 C1 1.3673(19) .
N2 C3 1.396(2) .
N2 C9 1.478(2) .
N3 C12 1.384(2) .
N3 H1N 0.8401 .
C2 C3 1.351(3) .
C2 C4 1.501(2) .
C3 C5 1.499(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C8 1.519(3) .
C6 C7 1.530(3) .
C6 H6 1.0000 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C11 1.521(3) .
C9 C10 1.535(2) .
C9 H9 1.0000 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.408(2) .
C12 C17 1.432(2) .
C13 C14 1.392(3) .
C13 C21 1.523(2) .
C14 C15 1.369(3) .
C14 H14 0.9500 .
C15 C16 1.393(4) .
C15 H15 0.9500 .
C16 C17 1.399(3) .
C16 H16 0.9500 .
C17 C18 1.507(3) .
C18 C20 1.530(3) .
C18 C19 1.535(3) .
C18 H18 0.8801 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C23 1.517(3) .
C21 C22 1.529(3) .
C21 H21 1.0000 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
