#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:01:05 +0100 (mar 22 de mar de 2016) $
#$Revision: 178969 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/98/4119870.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_4119870
loop_
_publ_author_name
'Randara Pulukkody'
'Samuel J. Kyran'
'Ryan D. Bethel'
'Chung-Hung Hsieh'
'Michael B. Hall'
'Donald J. Darensbourg'
'Marcetta Y. Darensbourg'
_publ_section_title
;
 Carbon Monoxide Induced Reductive Elimination of Disulfide in an
 N-Heterocyclic Carbene (NHC)/ Thiolate Dinitrosyl Iron Complex (DNIC)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8423
_journal_page_last               8430
_journal_paper_doi               10.1021/ja403916v
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C22 H26 Fe N4 O3'
_chemical_formula_weight         450.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 106.007(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.767(5)
_cell_length_b                   7.5444(19)
_cell_length_c                   16.488(4)
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.25
_cell_volume                     2244.0(10)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25673
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.8724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.560
_refine_diff_density_min         -1.003
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0389
_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)+(0.0470P)²+1.2603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                4512
_reflns_number_total             5561
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja403916v_si_002_1.cif
_cod_data_source_block           datax
_cod_original_cell_volume        2243.9(10)
_cod_database_code               4119870
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.750768(14) 1.09273(3) 0.059547(18) 0.03221(10) Uani 1 1 d .
N1 N 0.68095(9) 1.2301(2) 0.05580(11) 0.0343(4) Uani 1 1 d .
N2 N 0.76035(10) 1.0201(2) -0.03492(11) 0.0378(4) Uani 1 1 d .
O1 O 0.63593(9) 1.3417(2) 0.04773(13) 0.0602(5) Uani 1 1 d .
O2 O 0.76792(11) 0.9865(2) -0.10091(9) 0.0552(4) Uani 1 1 d .
C1 C 0.83634(9) 1.1886(2) 0.11551(11) 0.0258(3) Uani 1 1 d .
O3 O 0.89023(8) 1.2632(2) 0.14639(10) 0.0475(4) Uani 1 1 d .
C2 C 0.74602(9) 0.8801(2) 0.13015(10) 0.0237(3) Uani 1 1 d .
C3 C 0.77870(11) 0.6052(2) 0.19878(13) 0.0350(4) Uani 1 1 d .
H3A H 0.8174 0.5840 0.2506 0.042 Uiso 1 1 calc R
H3B H 0.7695 0.4970 0.1657 0.042 Uiso 1 1 calc R
C4 C 0.70810(11) 0.6735(3) 0.21670(13) 0.0358(4) Uani 1 1 d .
H4A H 0.6682 0.5878 0.1998 0.043 Uiso 1 1 calc R
H4B H 0.7163 0.7009 0.2761 0.043 Uiso 1 1 calc R
C5 C 0.86629(9) 0.7552(2) 0.12717(11) 0.0253(3) Uani 1 1 d .
C6 C 0.86836(11) 0.6855(2) 0.04940(12) 0.0300(4) Uani 1 1 d .
C7 C 0.93492(12) 0.6982(3) 0.02768(13) 0.0376(4) Uani 1 1 d .
H7 H 0.9375 0.6524 -0.0238 0.045 Uiso 1 1 calc R
C8 C 0.99728(11) 0.7766(3) 0.08029(15) 0.0401(5) Uani 1 1 d .
C9 C 0.99346(10) 0.8397(3) 0.15770(14) 0.0370(4) Uani 1 1 d .
H9 H 1.0354 0.8910 0.1938 0.044 Uiso 1 1 calc R
C10 C 0.92910(10) 0.8288(2) 0.18314(12) 0.0297(4) Uani 1 1 d .
C11 C 0.92737(12) 0.8945(3) 0.26893(13) 0.0411(5) Uani 1 1 d .
H11A H 0.9284 0.7952 0.3056 0.062 Uiso 1 1 calc R
H11B H 0.8829 0.9616 0.2638 0.062 Uiso 1 1 calc R
H11C H 0.9697 0.9685 0.2920 0.062 Uiso 1 1 calc R
C12 C 0.80201(13) 0.5979(3) -0.00920(13) 0.0388(5) Uani 1 1 d .
H12A H 0.8060 0.6036 -0.0659 0.058 Uiso 1 1 calc R
H12B H 0.7578 0.6581 -0.0061 0.058 Uiso 1 1 calc R
H12C H 0.7998 0.4762 0.0069 0.058 Uiso 1 1 calc R
C13 C 1.06779(14) 0.7939(4) 0.0535(2) 0.0624(7) Uani 1 1 d .
H13A H 1.0636 0.7247 0.0035 0.094 Uiso 1 1 calc R
H13B H 1.1090 0.7519 0.0979 0.094 Uiso 1 1 calc R
H13C H 1.0756 0.9160 0.0419 0.094 Uiso 1 1 calc R
C14 C 0.62731(10) 0.9386(2) 0.16340(11) 0.0265(3) Uani 1 1 d .
C15 C 0.55881(10) 0.8831(2) 0.11203(12) 0.0299(4) Uani 1 1 d .
C16 C 0.49636(11) 0.9825(3) 0.11269(13) 0.0356(4) Uani 1 1 d .
H16 H 0.4503 0.9473 0.0787 0.043 Uiso 1 1 calc R
C17 C 0.50093(11) 1.1328(3) 0.16280(13) 0.0368(4) Uani 1 1 d .
C18 C 0.56996(12) 1.1806(3) 0.21463(13) 0.0371(4) Uani 1 1 d .
H18 H 0.5736 1.2794 0.2493 0.045 Uiso 1 1 calc R
C19 C 0.63378(11) 1.0855(2) 0.21634(12) 0.0317(4) Uani 1 1 d .
C20 C 0.70731(12) 1.1407(3) 0.27476(14) 0.0450(5) Uani 1 1 d .
H20A H 0.7335 1.0378 0.3016 0.067 Uiso 1 1 calc R
H20B H 0.6991 1.2199 0.3169 0.067 Uiso 1 1 calc R
H20C H 0.7361 1.1997 0.2429 0.067 Uiso 1 1 calc R
C21 C 0.55110(12) 0.7182(3) 0.05892(14) 0.0408(5) Uani 1 1 d .
H21A H 0.5499 0.6161 0.0933 0.061 Uiso 1 1 calc R
H21B H 0.5925 0.7091 0.0356 0.061 Uiso 1 1 calc R
H21C H 0.5060 0.7241 0.0140 0.061 Uiso 1 1 calc R
C22 C 0.43310(13) 1.2412(4) 0.16097(17) 0.0558(6) Uani 1 1 d .
H22A H 0.4341 1.2750 0.2174 0.084 Uiso 1 1 calc R
H22B H 0.3894 1.1722 0.1368 0.084 Uiso 1 1 calc R
H22C H 0.4325 1.3457 0.1275 0.084 Uiso 1 1 calc R
N3 N 0.79820(8) 0.75279(19) 0.15045(9) 0.0266(3) Uani 1 1 d .
N4 N 0.69169(8) 0.8351(2) 0.16446(9) 0.0276(3) 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 Fe1 N2 116.58(8)
N1 Fe1 C1 110.95(8)
N2 Fe1 C1 107.34(8)
N1 Fe1 C2 111.21(8)
N2 Fe1 C2 107.87(7)
C1 Fe1 C2 101.78(7)
O1 N1 Fe1 171.48(17)
O2 N2 Fe1 173.85(16)
O3 C1 Fe1 173.66(16)
N4 C2 N3 107.48(14)
N4 C2 Fe1 127.67(12)
N3 C2 Fe1 124.84(12)
N3 C3 C4 102.04(14)
N4 C4 C3 102.63(14)
C10 C5 C6 121.64(16)
C10 C5 N3 118.75(15)
C6 C5 N3 119.61(16)
C7 C6 C5 117.62(18)
C7 C6 C12 120.49(18)
C5 C6 C12 121.89(17)
C8 C7 C6 122.10(19)
C9 C8 C7 118.42(18)
C9 C8 C13 120.9(2)
C7 C8 C13 120.7(2)
C8 C9 C10 122.04(19)
C9 C10 C5 118.09(17)
C9 C10 C11 120.70(18)
C5 C10 C11 121.21(17)
C19 C14 C15 121.69(16)
C19 C14 N4 119.82(16)
C15 C14 N4 118.40(16)
C16 C15 C14 118.02(17)
C16 C15 C21 120.20(18)
C14 C15 C21 121.76(17)
C17 C16 C15 121.92(18)
C18 C17 C16 118.11(18)
C18 C17 C22 120.7(2)
C16 C17 C22 121.1(2)
C17 C18 C19 122.06(18)
C18 C19 C14 118.15(18)
C18 C19 C20 120.12(18)
C14 C19 C20 121.73(17)
C2 N3 C5 124.46(14)
C2 N3 C3 113.67(14)
C5 N3 C3 121.86(14)
C2 N4 C14 126.39(15)
C2 N4 C4 113.30(14)
C14 N4 C4 119.77(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Fe1 N1 1.6584(16)
Fe1 N2 1.7066(19)
Fe1 C1 1.7711(18)
Fe1 C2 1.9984(17)
N1 O1 1.174(2)
N2 O2 1.164(2)
C1 O3 1.147(2)
C2 N4 1.339(2)
C2 N3 1.346(2)
C3 N3 1.473(2)
C3 C4 1.524(3)
C4 N4 1.475(2)
C5 C10 1.396(3)
C5 C6 1.396(3)
C5 N3 1.432(2)
C6 C7 1.394(3)
C6 C12 1.502(3)
C7 C8 1.383(3)
C8 C9 1.382(3)
C8 C13 1.512(3)
C9 C10 1.386(3)
C10 C11 1.507(3)
C14 C19 1.395(3)
C14 C15 1.395(3)
C14 N4 1.435(2)
C15 C16 1.394(3)
C15 C21 1.505(3)
C16 C17 1.392(3)
C17 C18 1.389(3)
C17 C22 1.506(3)
C18 C19 1.390(3)
C19 C20 1.508(3)
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
N2 Fe1 N1 O1 -62.0(12)
C1 Fe1 N1 O1 61.3(12)
C2 Fe1 N1 O1 173.8(12)
N1 Fe1 N2 O2 62.4(16)
C1 Fe1 N2 O2 -62.7(16)
C2 Fe1 N2 O2 -171.7(16)
N1 Fe1 C1 O3 -58.1(15)
N2 Fe1 C1 O3 70.3(15)
C2 Fe1 C1 O3 -176.5(15)
N1 Fe1 C2 N4 6.88(18)
N2 Fe1 C2 N4 -122.14(16)
C1 Fe1 C2 N4 125.09(16)
N1 Fe1 C2 N3 -174.36(14)
N2 Fe1 C2 N3 56.63(16)
C1 Fe1 C2 N3 -56.14(16)
N3 C3 C4 N4 8.8(2)
C10 C5 C6 C7 -2.5(3)
N3 C5 C6 C7 177.05(15)
C10 C5 C6 C12 176.89(16)
N3 C5 C6 C12 -3.5(2)
C5 C6 C7 C8 -0.1(3)
C12 C6 C7 C8 -179.52(18)
C6 C7 C8 C9 1.8(3)
C6 C7 C8 C13 -177.85(19)
C7 C8 C9 C10 -1.0(3)
C13 C8 C9 C10 178.67(19)
C8 C9 C10 C5 -1.5(3)
C8 C9 C10 C11 178.35(18)
C6 C5 C10 C9 3.3(3)
N3 C5 C10 C9 -176.28(16)
C6 C5 C10 C11 -176.55(17)
N3 C5 C10 C11 3.9(2)
C19 C14 C15 C16 2.1(3)
N4 C14 C15 C16 178.72(16)
C19 C14 C15 C21 -176.14(18)
N4 C14 C15 C21 0.5(3)
C14 C15 C16 C17 -0.2(3)
C21 C15 C16 C17 178.13(19)
C15 C16 C17 C18 -1.5(3)
C15 C16 C17 C22 178.4(2)
C16 C17 C18 C19 1.3(3)
C22 C17 C18 C19 -178.6(2)
C17 C18 C19 C14 0.6(3)
C17 C18 C19 C20 -179.0(2)
C15 C14 C19 C18 -2.3(3)
N4 C14 C19 C18 -178.86(16)
C15 C14 C19 C20 177.20(18)
N4 C14 C19 C20 0.7(3)
N4 C2 N3 C5 -178.33(15)
Fe1 C2 N3 C5 2.7(2)
N4 C2 N3 C3 2.6(2)
Fe1 C2 N3 C3 -176.39(13)
C10 C5 N3 C2 92.5(2)
C6 C5 N3 C2 -87.1(2)
C10 C5 N3 C3 -88.4(2)
C6 C5 N3 C3 92.0(2)
C4 C3 N3 C2 -7.6(2)
C4 C3 N3 C5 173.32(16)
N3 C2 N4 C14 175.61(16)
Fe1 C2 N4 C14 -5.4(3)
N3 C2 N4 C4 4.0(2)
Fe1 C2 N4 C4 -177.02(13)
C19 C14 N4 C2 -75.3(2)
C15 C14 N4 C2 108.0(2)
C19 C14 N4 C4 95.8(2)
C15 C14 N4 C4 -80.9(2)
C3 C4 N4 C2 -8.5(2)
C3 C4 N4 C14 179.33(16)
