#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:09:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179364 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/61/4326134.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_4326134
loop_
_publ_author_name
'Jennifer L. Hess'
'Chung-Hung Hsieh'
'Joseph H. Reibenspies'
'Marcetta Y. Darensbourg'
_publ_contact_author_address
;Department of Chemistry
Texas A&M University
College Station, TX 77843
;
_publ_contact_author_email       marcetta@mail.chem.tamu.edu
_publ_contact_author_name        'Marcetta Y. Darensbourg'
_publ_contact_author_phone       979-845-5417
_publ_section_title
;
 N-Heterocyclic Carbene Ligands as Mimics of Imidazoles/Histidine for the
 Stabilization of Di- and Trinitrosyl Iron Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8541
_journal_page_last               8552
_journal_paper_doi               10.1021/ic201138f
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C10 H16 Fe N4 O3'
_chemical_formula_weight         296.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 110.443(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.475(4)
_cell_length_b                   7.795(3)
_cell_length_c                   15.156(5)
_cell_measurement_reflns_used    3353
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.62
_cell_volume                     1381.0(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'bruker smart'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'ccd area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16106
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0643P)²+0.6961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2662
_reflns_number_total             3402
_reflns_threshold_expression     >2sigma(i)
_cod_data_source_file            ic201138f_si_002_2.cif
_cod_data_source_block           1
_cod_database_code               4326134
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.07817(16) 0.0266(2) 0.33610(13) 0.0174(4) Uani 1 1 d .
C2 C 0.22958(17) 0.2462(3) 0.34842(14) 0.0189(4) Uani 1 1 d .
H2 H 0.1644 0.3228 0.3196 0.023 Uiso 1 1 calc R
C3 C 0.28232(19) 0.2048(3) 0.27463(15) 0.0266(5) Uani 1 1 d .
H3A H 0.3450 0.1267 0.3006 0.040 Uiso 1 1 calc R
H3B H 0.3097 0.3085 0.2556 0.040 Uiso 1 1 calc R
H3C H 0.2257 0.1530 0.2210 0.040 Uiso 1 1 calc R
C4 C 0.3129(2) 0.3377(3) 0.43288(16) 0.0302(5) Uani 1 1 d .
H4A H 0.2797 0.3487 0.4810 0.045 Uiso 1 1 calc R
H4B H 0.3292 0.4496 0.4143 0.045 Uiso 1 1 calc R
H4C H 0.3825 0.2727 0.4568 0.045 Uiso 1 1 calc R
C5 C 0.25020(17) -0.0184(3) 0.44989(14) 0.0225(4) Uani 1 1 d .
H5 H 0.3264 -0.0034 0.4877 0.027 Uiso 1 1 calc R
C6 C 0.18126(18) -0.1477(3) 0.45465(14) 0.0221(4) Uani 1 1 d .
H6 H 0.2005 -0.2390 0.4968 0.027 Uiso 1 1 calc R
C7 C -0.02402(17) -0.2312(3) 0.36865(14) 0.0209(4) Uani 1 1 d .
H7 H -0.0865 -0.1858 0.3144 0.025 Uiso 1 1 calc R
C8 C 0.0019(2) -0.4104(3) 0.3445(2) 0.0372(6) Uani 1 1 d .
H8A H 0.0247 -0.4068 0.2903 0.056 Uiso 1 1 calc R
H8B H -0.0652 -0.4804 0.3311 0.056 Uiso 1 1 calc R
H8C H 0.0627 -0.4581 0.3968 0.056 Uiso 1 1 calc R
C9 C -0.0629(2) -0.2284(3) 0.45294(18) 0.0380(6) Uani 1 1 d .
H9A H -0.0027 -0.2713 0.5073 0.057 Uiso 1 1 calc R
H9B H -0.1295 -0.2992 0.4403 0.057 Uiso 1 1 calc R
H9C H -0.0810 -0.1128 0.4646 0.057 Uiso 1 1 calc R
N3 N -0.15368(18) 0.1577(3) 0.27013(14) 0.0357(5) Uani 1 1 d .
Fe1 Fe -0.04960(3) 0.11802(4) 0.22463(2) 0.02673(13) Uani 1 1 d .
N1 N 0.18585(14) 0.0880(2) 0.37784(11) 0.0185(4) Uani 1 1 d .
N2 N 0.07614(15) -0.1192(2) 0.38499(12) 0.0185(3) Uani 1 1 d .
C10 C -0.07660(17) -0.0679(3) 0.15142(14) 0.0222(4) Uani 1 1 d .
N4 N -0.00875(15) 0.2739(2) 0.16952(12) 0.0272(4) Uani 1 1 d .
O1 O -0.09502(15) -0.1827(2) 0.10067(12) 0.0381(4) Uani 1 1 d .
O2 O -0.22555(16) 0.1919(3) 0.30040(15) 0.0587(6) Uani 1 1 d .
O3 O 0.01138(16) 0.3857(2) 0.12429(12) 0.0405(5) Uani 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'
n n 0.0061 0.0033 'international tables vol c tables 4.2.6.8 and 6.1.1.4'
o o 0.0106 0.0060 '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
N1 C1 N2 104.13(16)
N1 C1 Fe1 129.34(14)
N2 C1 Fe1 126.48(14)
N1 C2 C4 110.74(16)
N1 C2 C3 110.22(16)
C4 C2 C3 112.12(18)
C6 C5 N1 106.64(18)
C5 C6 N2 107.01(18)
N2 C7 C8 110.41(17)
N2 C7 C9 110.60(17)
C8 C7 C9 112.12(19)
O2 N3 Fe1 177.3(2)
N4 Fe1 N3 119.07(10)
N4 Fe1 C10 107.91(10)
N3 Fe1 C10 113.29(10)
N4 Fe1 C1 113.10(8)
N3 Fe1 C1 102.60(9)
C10 Fe1 C1 99.04(9)
C1 N1 C5 111.34(17)
C1 N1 C2 124.26(16)
C5 N1 C2 124.38(17)
C1 N2 C6 110.87(17)
C1 N2 C7 125.40(17)
C6 N2 C7 123.72(17)
O1 C10 Fe1 176.78(19)
O3 N4 Fe1 174.36(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.356(3)
C1 N2 1.362(2)
C1 Fe1 2.005(2)
C2 N1 1.479(3)
C2 C4 1.516(3)
C2 C3 1.517(3)
C5 C6 1.343(3)
C5 N1 1.383(3)
C6 N2 1.384(3)
C7 N2 1.473(3)
C7 C8 1.507(3)
C7 C9 1.516(3)
N3 O2 1.172(3)
N3 Fe1 1.698(2)
Fe1 N4 1.6525(19)
Fe1 C10 1.784(2)
C10 O1 1.150(3)
N4 O3 1.189(2)
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
N1 C5 C6 N2 0.5(2)
O2 N3 Fe1 N4 -3(4)
O2 N3 Fe1 C10 -132(4)
O2 N3 Fe1 C1 122(4)
N1 C1 Fe1 N4 9.2(2)
N2 C1 Fe1 N4 -167.83(16)
N1 C1 Fe1 N3 -120.34(18)
N2 C1 Fe1 N3 62.62(18)
N1 C1 Fe1 C10 123.18(18)
N2 C1 Fe1 C10 -53.86(18)
N2 C1 N1 C5 1.1(2)
Fe1 C1 N1 C5 -176.45(14)
N2 C1 N1 C2 179.66(16)
Fe1 C1 N1 C2 2.1(3)
C6 C5 N1 C1 -1.0(2)
C6 C5 N1 C2 -179.58(18)
C4 C2 N1 C1 145.33(19)
C3 C2 N1 C1 -90.0(2)
C4 C2 N1 C5 -36.3(3)
C3 C2 N1 C5 88.4(2)
N1 C1 N2 C6 -0.8(2)
Fe1 C1 N2 C6 176.87(14)
N1 C1 N2 C7 177.91(17)
Fe1 C1 N2 C7 -4.5(3)
C5 C6 N2 C1 0.2(2)
C5 C6 N2 C7 -178.53(17)
C8 C7 N2 C1 121.0(2)
C9 C7 N2 C1 -114.3(2)
C8 C7 N2 C6 -60.5(3)
C9 C7 N2 C6 64.2(3)
N4 Fe1 C10 O1 -26(3)
N3 Fe1 C10 O1 108(3)
C1 Fe1 C10 O1 -144(3)
N3 Fe1 N4 O3 -64.2(19)
C10 Fe1 N4 O3 66.7(19)
C1 Fe1 N4 O3 175.2(19)
