#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:14:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178841 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/95/4109591.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_4109591
loop_
_publ_author_name
'Azwana R. Sadique'
'Elizabeth A. Gregory'
'William W. Brennessel'
'Patrick L. Holland'
_publ_section_title
;
 Mechanistic Insight into NN Cleavage by a Low-Coordinate Iron(II) Hydride
 Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8112
_journal_page_last               8121
_journal_paper_doi               10.1021/ja069199r
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C47 H63 Fe N4'
_chemical_formula_sum            'C47 H63 Fe N4'
_chemical_formula_weight         739.86
_chemical_name_common            holas19
_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                 115.543(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.938(4)
_cell_length_b                   10.2673(17)
_cell_length_c                   19.629(3)
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      33.08
_cell_measurement_theta_min      2.68
_cell_volume                     4171.0(12)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'APEX2, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97, CNR-IC'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, ω scans per φ'
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27124
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.9538
_exptl_absorpt_correction_T_min  0.8833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            red-black
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       block
_exptl_crystal_F_000             1596
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.008
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         7230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+1.5728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                5927
_reflns_number_total             7230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja069199rsi20061221_093140.cif
_cod_data_source_block           holas19
_cod_original_cell_volume        4170.9(12)
_cod_database_code               4109591
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
Fe Fe 0.0000 0.47523(2) 0.2500 0.01286(6) Uani 1 2 d S
N1 N 0.03167(4) 0.29764(9) 0.27830(5) 0.01564(17) Uani 1 1 d .
C1 C 0.03579(5) 0.25583(10) 0.34921(6) 0.0166(2) Uani 1 1 d .
C2 C 0.09521(6) 0.27040(12) 0.41236(7) 0.0212(2) Uani 1 1 d .
H2A H 0.1304 0.3104 0.4072 0.025 Uiso 1 1 calc R
C3 C 0.10263(7) 0.22638(13) 0.48258(7) 0.0265(3) Uani 1 1 d .
H3A H 0.1426 0.2394 0.5256 0.032 Uiso 1 1 calc R
C4 C 0.05237(7) 0.16356(14) 0.49056(7) 0.0297(3) Uani 1 1 d .
H4A H 0.0577 0.1337 0.5387 0.036 Uiso 1 1 calc R
C5 C -0.00563(7) 0.14481(13) 0.42762(8) 0.0278(3) Uani 1 1 d .
H5A H -0.0398 0.0998 0.4326 0.033 Uiso 1 1 calc R
C6 C -0.01449(6) 0.19108(12) 0.35720(7) 0.0211(2) Uani 1 1 d .
H6A H -0.0547 0.1787 0.3145 0.025 Uiso 1 1 calc R
N11 N 0.07202(4) 0.60282(9) 0.29174(5) 0.01297(16) Uani 1 1 d .
C11 C 0.11607(5) 0.83644(11) 0.29436(6) 0.01523(19) Uani 1 1 d .
C21 C 0.06223(5) 0.73178(10) 0.28058(6) 0.01372(18) Uani 1 1 d .
C31 C 0.0000 0.78634(15) 0.2500 0.0158(3) Uani 1 2 d S
H31A H 0.0000 0.8789 0.2500 0.019 Uiso 1 2 calc SR
C41 C 0.18722(5) 0.79425(12) 0.33653(6) 0.0187(2) Uani 1 1 d .
H41A H 0.1945 0.7160 0.3127 0.028 Uiso 1 1 calc R
H41B H 0.1971 0.7753 0.3893 0.028 Uiso 1 1 calc R
H41C H 0.2153 0.8646 0.3345 0.028 Uiso 1 1 calc R
C51 C 0.10559(6) 0.88092(12) 0.21459(7) 0.0219(2) Uani 1 1 d .
H51A H 0.1105 0.8061 0.1865 0.033 Uiso 1 1 calc R
H51B H 0.1376 0.9476 0.2190 0.033 Uiso 1 1 calc R
H51C H 0.0620 0.9172 0.1878 0.033 Uiso 1 1 calc R
C61 C 0.10839(6) 0.95624(12) 0.33756(7) 0.0227(2) Uani 1 1 d .
H61A H 0.1079 0.9277 0.3850 0.034 Uiso 1 1 calc R
H61B H 0.0677 1.0008 0.3065 0.034 Uiso 1 1 calc R
H61C H 0.1446 1.0161 0.3486 0.034 Uiso 1 1 calc R
C12 C 0.13185(5) 0.55243(10) 0.34809(6) 0.01332(18) Uani 1 1 d .
C22 C 0.17128(5) 0.47044(11) 0.32793(6) 0.01599(19) Uani 1 1 d .
C32 C 0.22845(5) 0.42392(12) 0.38562(7) 0.0214(2) Uani 1 1 d .
H32A H 0.2565 0.3715 0.3730 0.026 Uiso 1 1 calc R
C42 C 0.24529(6) 0.45230(13) 0.46084(7) 0.0231(2) Uani 1 1 d .
H42A H 0.2847 0.4204 0.4991 0.028 Uiso 1 1 calc R
C52 C 0.20431(6) 0.52751(12) 0.47984(6) 0.0198(2) Uani 1 1 d .
H52A H 0.2153 0.5441 0.5315 0.024 Uiso 1 1 calc R
C62 C 0.14726(5) 0.57941(11) 0.42450(6) 0.01521(19) Uani 1 1 d .
C72 C 0.15333(5) 0.43104(12) 0.24640(6) 0.0182(2) Uani 1 1 d .
H72A H 0.1051 0.4315 0.2187 0.022 Uiso 1 1 calc R
C82 C 0.17661(6) 0.29330(12) 0.24081(7) 0.0234(2) Uani 1 1 d .
H82A H 0.1643 0.2335 0.2713 0.035 Uiso 1 1 calc R
H82B H 0.2237 0.2935 0.2596 0.035 Uiso 1 1 calc R
H82C H 0.1567 0.2648 0.1880 0.035 Uiso 1 1 calc R
C92 C 0.17949(8) 0.52676(14) 0.20624(8) 0.0319(3) Uani 1 1 d .
H92A H 0.1600 0.6127 0.2036 0.048 Uiso 1 1 calc R
H92B H 0.1686 0.4954 0.1550 0.048 Uiso 1 1 calc R
H92C H 0.2265 0.5333 0.2344 0.048 Uiso 1 1 calc R
C102 C 0.10357(5) 0.66102(11) 0.44820(6) 0.0176(2) Uani 1 1 d .
H10A H 0.0779 0.7201 0.4051 0.021 Uiso 1 1 calc R
C112 C 0.14154(6) 0.74673(13) 0.51689(7) 0.0259(3) Uani 1 1 d .
H11A H 0.1753 0.7939 0.5090 0.039 Uiso 1 1 calc R
H11B H 0.1615 0.6920 0.5620 0.039 Uiso 1 1 calc R
H11C H 0.1122 0.8092 0.5237 0.039 Uiso 1 1 calc R
C122 C 0.05560(7) 0.57481(14) 0.46277(9) 0.0307(3) Uani 1 1 d .
H12A H 0.0288 0.5269 0.4166 0.046 Uiso 1 1 calc R
H12B H 0.0280 0.6294 0.4776 0.046 Uiso 1 1 calc R
H12C H 0.0794 0.5130 0.5034 0.046 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
N1 Fe N1 41.94(5) 2 .
N1 Fe N11 150.93(4) 2 .
N1 Fe N11 110.92(4) . .
N1 Fe N11 110.92(4) 2 2
N1 Fe N11 150.93(4) . 2
N11 Fe N11 97.52(5) . 2
N1 N1 C1 112.70(10) 2 .
N1 N1 Fe 69.03(3) 2 .
C1 N1 Fe 114.85(7) . .
C6 C1 C2 119.15(10) . .
C6 C1 N1 122.98(10) . .
C2 C1 N1 117.61(10) . .
C3 C2 C1 119.99(12) . .
C3 C2 H2A 120.0 . .
C1 C2 H2A 120.0 . .
C4 C3 C2 120.71(12) . .
C4 C3 H3A 119.6 . .
C2 C3 H3A 119.6 . .
C5 C4 C3 119.31(12) . .
C5 C4 H4A 120.3 . .
C3 C4 H4A 120.3 . .
C4 C5 C6 120.78(12) . .
C4 C5 H5A 119.6 . .
C6 C5 H5A 119.6 . .
C5 C6 C1 119.99(12) . .
C5 C6 H6A 120.0 . .
C1 C6 H6A 120.0 . .
C21 N11 C12 121.11(9) . .
C21 N11 Fe 122.08(7) . .
C12 N11 Fe 115.35(7) . .
C41 C11 C61 105.89(9) . .
C41 C11 C51 107.05(9) . .
C61 C11 C51 108.38(10) . .
C41 C11 C21 118.21(9) . .
C61 C11 C21 111.82(9) . .
C51 C11 C21 105.09(8) . .
N11 C21 C31 121.99(10) . .
N11 C21 C11 125.59(9) . .
C31 C21 C11 112.31(10) . .
C21 C31 C21 132.99(14) 2 .
C21 C31 H31A 113.5 2 .
C21 C31 H31A 113.5 . .
C11 C41 H41A 109.5 . .
C11 C41 H41B 109.5 . .
H41A C41 H41B 109.5 . .
C11 C41 H41C 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C11 C51 H51A 109.5 . .
C11 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C11 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C11 C61 H61A 109.5 . .
C11 C61 H61B 109.5 . .
H61A C61 H61B 109.5 . .
C11 C61 H61C 109.5 . .
H61A C61 H61C 109.5 . .
H61B C61 H61C 109.5 . .
C22 C12 C62 121.17(10) . .
C22 C12 N11 120.91(9) . .
C62 C12 N11 117.74(9) . .
C32 C22 C12 117.90(10) . .
C32 C22 C72 119.64(10) . .
C12 C22 C72 122.46(10) . .
C42 C32 C22 121.65(10) . .
C42 C32 H32A 119.2 . .
C22 C32 H32A 119.2 . .
C52 C42 C32 119.59(11) . .
C52 C42 H42A 120.2 . .
C32 C42 H42A 120.2 . .
C42 C52 C62 121.33(10) . .
C42 C52 H52A 119.3 . .
C62 C52 H52A 119.3 . .
C52 C62 C12 118.21(10) . .
C52 C62 C102 119.41(9) . .
C12 C62 C102 122.37(9) . .
C22 C72 C82 112.04(10) . .
C22 C72 C92 112.37(10) . .
C82 C72 C92 109.20(10) . .
C22 C72 H72A 107.7 . .
C82 C72 H72A 107.7 . .
C92 C72 H72A 107.7 . .
C72 C82 H82A 109.5 . .
C72 C82 H82B 109.5 . .
H82A C82 H82B 109.5 . .
C72 C82 H82C 109.5 . .
H82A C82 H82C 109.5 . .
H82B C82 H82C 109.5 . .
C72 C92 H92A 109.5 . .
C72 C92 H92B 109.5 . .
H92A C92 H92B 109.5 . .
C72 C92 H92C 109.5 . .
H92A C92 H92C 109.5 . .
H92B C92 H92C 109.5 . .
C62 C102 C112 112.70(9) . .
C62 C102 C122 111.03(10) . .
C112 C102 C122 110.47(10) . .
C62 C102 H10A 107.5 . .
C112 C102 H10A 107.5 . .
C122 C102 H10A 107.5 . .
C102 C112 H11A 109.5 . .
C102 C112 H11B 109.5 . .
H11A C112 H11B 109.5 . .
C102 C112 H11C 109.5 . .
H11A C112 H11C 109.5 . .
H11B C112 H11C 109.5 . .
C102 C122 H12A 109.5 . .
C102 C122 H12B 109.5 . .
H12A C122 H12B 109.5 . .
C102 C122 H12C 109.5 . .
H12A C122 H12C 109.5 . .
H12B C122 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe N1 1.9527(10) 2
Fe N1 1.9527(10) .
Fe N11 1.9871(9) .
Fe N11 1.9871(9) 2
N1 N1 1.3976(18) 2
N1 C1 1.4203(14) .
C1 C6 1.3974(16) .
C1 C2 1.3998(16) .
C2 C3 1.3894(17) .
C2 H2A 0.9500 .
C3 C4 1.388(2) .
C3 H3A 0.9500 .
C4 C5 1.384(2) .
C4 H4A 0.9500 .
C5 C6 1.3912(17) .
C5 H5A 0.9500 .
C6 H6A 0.9500 .
N11 C21 1.3451(14) .
N11 C12 1.4372(13) .
C11 C41 1.5398(15) .
C11 C61 1.5466(16) .
C11 C51 1.5471(15) .
C11 C21 1.5701(15) .
C21 C31 1.4045(12) .
C31 C21 1.4045(12) 2
C31 H31A 0.9500 .
C41 H41A 0.9800 .
C41 H41B 0.9800 .
C41 H41C 0.9800 .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
C61 H61A 0.9800 .
C61 H61B 0.9800 .
C61 H61C 0.9800 .
C12 C22 1.4115(14) .
C12 C62 1.4121(14) .
C22 C32 1.3962(15) .
C22 C72 1.5250(15) .
C32 C42 1.3866(17) .
C32 H32A 0.9500 .
C42 C52 1.3860(17) .
C42 H42A 0.9500 .
C52 C62 1.3966(15) .
C52 H52A 0.9500 .
C62 C102 1.5247(15) .
C72 C82 1.5322(17) .
C72 C92 1.5345(18) .
C72 H72A 1.0000 .
C82 H82A 0.9800 .
C82 H82B 0.9800 .
C82 H82C 0.9800 .
C92 H92A 0.9800 .
C92 H92B 0.9800 .
C92 H92C 0.9800 .
C102 C112 1.5291(16) .
C102 C122 1.5323(17) .
C102 H10A 1.0000 .
C112 H11A 0.9800 .
C112 H11B 0.9800 .
C112 H11C 0.9800 .
C122 H12A 0.9800 .
C122 H12B 0.9800 .
C122 H12C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N11 Fe N1 N1 -167.05(7) . 2
N11 Fe N1 N1 25.52(12) 2 2
N1 Fe N1 C1 -106.14(11) 2 .
N11 Fe N1 C1 86.81(8) . .
N11 Fe N1 C1 -80.62(10) 2 .
N1 N1 C1 C6 15.29(12) 2 .
Fe N1 C1 C6 91.77(11) . .
N1 N1 C1 C2 -170.63(8) 2 .
Fe N1 C1 C2 -94.14(10) . .
C6 C1 C2 C3 -3.12(17) . .
N1 C1 C2 C3 -177.44(10) . .
C1 C2 C3 C4 2.35(18) . .
C2 C3 C4 C5 0.0(2) . .
C3 C4 C5 C6 -1.7(2) . .
C4 C5 C6 C1 0.85(19) . .
C2 C1 C6 C5 1.54(17) . .
N1 C1 C6 C5 175.54(11) . .
N1 Fe N11 C21 162.76(8) 2 .
N1 Fe N11 C21 -179.28(8) . .
N11 Fe N11 C21 -5.41(6) 2 .
N1 Fe N11 C12 -30.90(11) 2 .
N1 Fe N11 C12 -12.95(8) . .
N11 Fe N11 C12 160.93(8) 2 .
C12 N11 C21 C31 -154.61(8) . .
Fe N11 C21 C31 10.95(13) . .
C12 N11 C21 C11 29.48(15) . .
Fe N11 C21 C11 -164.96(7) . .
C41 C11 C21 N11 -11.02(15) . .
C61 C11 C21 N11 -134.36(11) . .
C51 C11 C21 N11 108.27(11) . .
C41 C11 C21 C31 172.73(8) . .
C61 C11 C21 C31 49.39(11) . .
C51 C11 C21 C31 -67.98(10) . .
N11 C21 C31 C21 -6.27(15) . 2
C11 C21 C31 C21 170.14(8) . 2
C21 N11 C12 C22 -119.18(11) . .
Fe N11 C12 C22 74.33(11) . .
C21 N11 C12 C62 65.62(13) . .
Fe N11 C12 C62 -100.87(10) . .
C62 C12 C22 C32 -4.33(16) . .
N11 C12 C22 C32 -179.36(10) . .
C62 C12 C22 C72 175.21(10) . .
N11 C12 C22 C72 0.18(16) . .
C12 C22 C32 C42 2.53(18) . .
C72 C22 C32 C42 -177.02(11) . .
C22 C32 C42 C52 0.7(2) . .
C32 C42 C52 C62 -2.28(19) . .
C42 C52 C62 C12 0.51(18) . .
C42 C52 C62 C102 179.71(11) . .
C22 C12 C62 C52 2.85(16) . .
N11 C12 C62 C52 178.04(10) . .
C22 C12 C62 C102 -176.32(10) . .
N11 C12 C62 C102 -1.14(15) . .
C32 C22 C72 C82 32.74(15) . .
C12 C22 C72 C82 -146.79(11) . .
C32 C22 C72 C92 -90.65(14) . .
C12 C22 C72 C92 89.82(13) . .
C52 C62 C102 C112 36.96(15) . .
C12 C62 C102 C112 -143.88(11) . .
C52 C62 C102 C122 -87.58(13) . .
C12 C62 C102 C122 91.58(13) . .
