#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:08:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178618 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/29/4072970.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_4072970
loop_
_publ_author_name
'Morvan, Didier'
'Capon, Jean-François'
'Gloaguen, Frédéric'
'Le Goff, Alan'
'Marchivie, Mathieu'
'Michaud, François'
'Schollhammer, Philippe'
'Talarmin, Jean'
'Yaouanc, Jean-Jacques'
'Pichon, Roger'
'Kervarec, Nelly'
_publ_section_title
;
 N-Heterocyclic Carbene Ligands in Nonsymmetric Diiron Models of
 Hydrogenase Active Sites
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              2042
_journal_paper_doi               10.1021/om061173l
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C17 H23 Fe2 N3 O5.25 S2'
_chemical_formula_weight         529.2
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-12-21T16:52:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                114.724(7)
_cell_angle_beta                 92.134(5)
_cell_angle_gamma                96.054(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4095(5)
_cell_length_b                   11.8025(8)
_cell_length_c                   12.8638(10)
_cell_measurement_temperature    150(2)
_cell_volume                     1148.58(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14497
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    1.477
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.53
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0878P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.111
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2750
_reflns_number_total             3190
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om061173lsi20061222_014118.cif
_cod_data_source_block           nch32
_cod_original_cell_volume        1148.58(14)
_cod_database_code               4072970
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9332(4) 0.3506(4) 0.3591(3) 0.0354(9) Uani 1 1 d . B .
C2 C 0.9308(4) 0.2616(4) 0.5020(4) 0.0341(9) Uani 1 1 d . B .
C3 C 0.6777(5) 0.1217(4) 0.1713(4) 0.0429(10) Uani 1 1 d . . .
C4 C 0.7558(5) -0.1157(4) 0.1118(4) 0.0415(10) Uani 1 1 d . . .
C5 C 0.6588(5) 0.0353(3) 0.3249(4) 0.0360(9) Uani 1 1 d . . .
C6 C 1.1703(5) 0.0270(4) 0.1294(4) 0.0480(11) Uani 1 1 d . . .
H6A H 1.1237 -0.0516 0.063 0.058 Uiso 1 1 calc R A 1
H6B H 1.2557 0.0687 0.1015 0.058 Uiso 1 1 calc R A 1
C7A C 1.2466(10) -0.0079(8) 0.2130(7) 0.039(3) Uani 0.583(14) 1 d P B 1
H7A1 H 1.3091 0.0691 0.273 0.047 Uiso 0.583(14) 1 calc PR B 1
H7A2 H 1.3243 -0.0659 0.1737 0.047 Uiso 0.583(14) 1 calc PR B 1
C7B C 1.1586(14) -0.0848(11) 0.1493(11) 0.045(4) Uani 0.417(14) 1 d P B 2
H7B1 H 1.2554 -0.1259 0.123 0.053 Uiso 0.417(14) 1 calc PR B 2
H7B2 H 1.0649 -0.1432 0.1001 0.053 Uiso 0.417(14) 1 calc PR B 2
C8 C 1.1421(5) -0.0686(4) 0.2718(4) 0.0420(10) Uani 1 1 d . . .
H8A H 1.2114 -0.0831 0.3278 0.05 Uiso 1 1 calc R B 1
H8B H 1.0921 -0.1521 0.2136 0.05 Uiso 1 1 calc R B 1
C9 C 1.2337(4) 0.2829(3) 0.4114(3) 0.0297(8) Uani 1 1 d . B .
C10 C 1.4902(4) 0.3596(4) 0.4070(3) 0.0369(9) Uani 1 1 d . . .
H10 H 1.5807 0.3975 0.3857 0.044 Uiso 1 1 calc R . .
C11 C 1.4920(4) 0.3117(4) 0.4831(3) 0.0364(9) Uani 1 1 d . . .
H11 H 1.5837 0.3095 0.5273 0.044 Uiso 1 1 calc R . .
C12 C 1.2855(5) 0.3921(4) 0.2821(4) 0.0475(11) Uani 1 1 d . . .
H12A H 1.3811 0.4317 0.2627 0.071 Uiso 1 1 calc R . .
H12B H 1.2119 0.4544 0.3158 0.071 Uiso 1 1 calc R . .
H12C H 1.2316 0.3225 0.2123 0.071 Uiso 1 1 calc R . .
C13 C 1.2917(5) 0.2081(3) 0.5641(3) 0.0351(9) Uani 1 1 d . . .
H13A H 1.3721 0.1529 0.5648 0.042 Uiso 1 1 calc R . .
H13B H 1.1865 0.1548 0.5345 0.042 Uiso 1 1 calc R . .
C14 C 1.2812(5) 0.3031(4) 0.6850(3) 0.0405(10) Uani 1 1 d . . .
H14A H 1.2031 0.3597 0.6836 0.049 Uiso 1 1 calc R . .
H14B H 1.2392 0.2583 0.7304 0.049 Uiso 1 1 calc R . .
C15 C 1.5469(6) 0.3064(6) 0.7681(5) 0.0674(15) Uani 1 1 d . . .
H15A H 1.5637 0.2349 0.6968 0.101 Uiso 1 1 calc R . .
H15B H 1.5036 0.2755 0.8225 0.101 Uiso 1 1 calc R . .
H15C H 1.6495 0.3601 0.8018 0.101 Uiso 1 1 calc R . .
C16 C 1.4072(7) 0.4855(5) 0.8481(4) 0.0729(16) Uani 1 1 d . . .
H16A H 1.3315 0.5342 0.8306 0.109 Uiso 1 1 calc R . .
H16B H 1.5094 0.5393 0.8826 0.109 Uiso 1 1 calc R . .
H16C H 1.3628 0.4544 0.9022 0.109 Uiso 1 1 calc R . .
N1 N 1.3326(4) 0.3444(3) 0.3641(3) 0.0337(7) Uani 1 1 d . . .
N2 N 1.3361(3) 0.2656(3) 0.4864(3) 0.0295(7) Uani 1 1 d . . .
N3 N 1.4334(4) 0.3795(3) 0.7429(3) 0.0480(9) Uani 1 1 d . . .
O1 O 0.8782(3) 0.4348(3) 0.3554(3) 0.0532(8) Uani 1 1 d . . .
O2 O 0.8784(3) 0.2891(3) 0.5901(2) 0.0499(7) Uani 1 1 d . . .
O3 O 0.5990(4) 0.1718(3) 0.1356(3) 0.0661(9) Uani 1 1 d . . .
O4 O 0.7232(4) -0.2142(3) 0.0390(3) 0.0586(9) Uani 1 1 d . . .
O5 O 0.5704(3) 0.0310(3) 0.3888(3) 0.0489(7) Uani 1 1 d . . .
S1 S 1.01335(11) 0.12908(9) 0.17284(8) 0.0334(3) Uani 1 1 d . B .
S2 S 0.98318(11) 0.01751(8) 0.34711(8) 0.0311(3) Uani 1 1 d . B .
Fe1 Fe 1.00291(6) 0.21845(4) 0.36570(4) 0.0279(2) Uani 1 1 d . . .
Fe2 Fe 0.79965(6) 0.03999(5) 0.22627(4) 0.0309(2) Uani 1 1 d . B .
C17 C 1.9608(11) 0.5143(11) 0.9117(9) 0.061(3) Uani 0.5 1 d P . 3
H10A H 1.8493 0.5346 0.9186 0.073 Uiso 0.5 1 calc PR . 3
H10B H 1.9874 0.498 0.8328 0.073 Uiso 0.5 1 calc PR . 3
C18 C 1.9685(13) 0.4074(13) 0.9277(14) 0.087(4) Uani 0.5 1 d P . 3
H10C H 1.9039 0.3401 0.8599 0.104 Uiso 0.5 1 calc PR . 3
H10D H 2.0813 0.3914 0.9168 0.104 Uiso 0.5 1 calc PR . 3
O6 O 1.935(3) 0.3807(19) 1.009(2) 0.142(9) Uani 0.25 1 d P . 3
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
O1 C1 Fe1 176.0(3) . .
O2 C2 Fe1 177.8(3) . .
O3 C3 Fe2 178.9(4) . .
O4 C4 Fe2 178.0(4) . .
O5 C5 Fe2 178.7(3) . .
C7B C6 C7A 45.1(5) . .
C7B C6 S1 119.5(5) . .
C7A C6 S1 119.0(4) . .
C7B C6 H6A 64.7 . .
C7A C6 H6A 107.6 . .
S1 C6 H6A 107.6 . .
C7B C6 H6B 132.7 . .
C7A C6 H6B 107.6 . .
S1 C6 H6B 107.6 . .
H6A C6 H6B 107 . .
C6 C7A C8 118.2(6) . .
C6 C7A H7A1 107.8 . .
C8 C7A H7A1 107.8 . .
C6 C7A H7A2 107.8 . .
C8 C7A H7A2 107.8 . .
H7A1 C7A H7A2 107.1 . .
C6 C7B C8 117.3(9) . .
C6 C7B H7B1 108 . .
C8 C7B H7B1 108 . .
C6 C7B H7B2 108 . .
C8 C7B H7B2 108 . .
H7B1 C7B H7B2 107.2 . .
C7A C8 C7B 43.2(5) . .
C7A C8 S2 116.4(3) . .
C7B C8 S2 117.6(4) . .
C7A C8 H8A 108.2 . .
C7B C8 H8A 133.3 . .
S2 C8 H8A 108.2 . .
C7A C8 H8B 108.2 . .
C7B C8 H8B 67.1 . .
S2 C8 H8B 108.2 . .
H8A C8 H8B 107.3 . .
N2 C9 N1 103.1(3) . .
N2 C9 Fe1 129.4(2) . .
N1 C9 Fe1 127.1(3) . .
C11 C10 N1 107.5(3) . .
C11 C10 H10 126.3 . .
N1 C10 H10 126.3 . .
C10 C11 N2 107.0(3) . .
C10 C11 H11 126.5 . .
N2 C11 H11 126.5 . .
N1 C12 H12A 109.5 . .
N1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N2 C13 C14 113.1(3) . .
N2 C13 H13A 109 . .
C14 C13 H13A 109 . .
N2 C13 H13B 109 . .
C14 C13 H13B 109 . .
H13A C13 H13B 107.8 . .
N3 C14 C13 114.4(3) . .
N3 C14 H14A 108.7 . .
C13 C14 H14A 108.7 . .
N3 C14 H14B 108.7 . .
C13 C14 H14B 108.7 . .
H14A C14 H14B 107.6 . .
N3 C15 H15A 109.5 . .
N3 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
N3 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
N3 C16 H16A 109.5 . .
N3 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
N3 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C9 N1 C10 110.8(3) . .
C9 N1 C12 126.9(3) . .
C10 N1 C12 122.3(3) . .
C9 N2 C11 111.6(3) . .
C9 N2 C13 126.2(3) . .
C11 N2 C13 122.3(3) . .
C16 N3 C14 110.6(4) . .
C16 N3 C15 109.9(4) . .
C14 N3 C15 112.5(4) . .
C6 S1 Fe2 111.95(14) . .
C6 S1 Fe1 112.16(14) . .
Fe2 S1 Fe1 68.19(3) . .
C8 S2 Fe2 112.26(13) . .
C8 S2 Fe1 114.00(13) . .
Fe2 S2 Fe1 68.02(3) . .
C1 Fe1 C2 89.18(17) . .
C1 Fe1 C9 100.14(16) . .
C2 Fe1 C9 100.09(16) . .
C1 Fe1 S1 90.57(13) . .
C2 Fe1 S1 161.24(13) . .
C9 Fe1 S1 98.42(10) . .
C1 Fe1 S2 155.81(13) . .
C2 Fe1 S2 88.20(12) . .
C9 Fe1 S2 104.00(10) . .
S1 Fe1 S2 84.38(4) . .
C1 Fe1 Fe2 102.05(13) . .
C2 Fe1 Fe2 105.95(12) . .
C9 Fe1 Fe2 145.76(10) . .
S1 Fe1 Fe2 55.84(3) . .
S2 Fe1 Fe2 55.88(3) . .
C5 Fe2 C3 92.39(17) . .
C5 Fe2 C4 102.02(17) . .
C3 Fe2 C4 99.47(18) . .
C5 Fe2 S1 153.65(13) . .
C3 Fe2 S1 87.20(13) . .
C4 Fe2 S1 104.04(12) . .
C5 Fe2 S2 85.64(12) . .
C3 Fe2 S2 156.95(14) . .
C4 Fe2 S2 103.42(13) . .
S1 Fe2 S2 84.60(4) . .
C5 Fe2 Fe1 98.55(13) . .
C3 Fe2 Fe1 101.73(14) . .
C4 Fe2 Fe1 149.66(13) . .
S1 Fe2 Fe1 55.98(3) . .
S2 Fe2 Fe1 56.10(3) . .
C18 C17 O6 113.4(14) . 2_967
C18 C17 C18 81.9(10) . 2_967
O6 C17 C18 40.6(12) 2_967 2_967
C18 C17 H10A 108.9 . .
O6 C17 H10A 108.9 2_967 .
C18 C17 H10A 97.5 2_967 .
C18 C17 H10B 108.9 . .
O6 C17 H10B 108.9 2_967 .
C18 C17 H10B 146.8 2_967 .
H10A C17 H10B 107.7 . .
O6 C18 C17 131.8(17) . .
O6 C18 C17 47.5(13) . 2_967
C17 C18 C17 98.1(10) . 2_967
O6 C18 H10C 104.3 . .
C17 C18 H10C 104.3 . .
C17 C18 H10C 151.8 2_967 .
O6 C18 H10D 104.3 . .
C17 C18 H10D 104.3 . .
C17 C18 H10D 84.9 2_967 .
H10C C18 H10D 105.6 . .
C18 O6 C17 91.9(19) . 2_967
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.157(4) .
C1 Fe1 1.756(4) .
C2 O2 1.159(4) .
C2 Fe1 1.760(4) .
C3 O3 1.134(5) .
C3 Fe2 1.791(4) .
C4 O4 1.143(5) .
C4 Fe2 1.799(5) .
C5 O5 1.142(4) .
C5 Fe2 1.781(4) .
C6 C7B 1.439(11) .
C6 C7A 1.454(8) .
C6 S1 1.825(4) .
C6 H6A 0.99 .
C6 H6B 0.99 .
C7A C8 1.493(8) .
C7A H7A1 0.99 .
C7A H7A2 0.99 .
C7B C8 1.520(11) .
C7B H7B1 0.99 .
C7B H7B2 0.99 .
C8 S2 1.821(4) .
C8 H8A 0.99 .
C8 H8B 0.99 .
C9 N2 1.361(5) .
C9 N1 1.367(4) .
C9 Fe1 1.980(4) .
C10 C11 1.320(5) .
C10 N1 1.380(5) .
C10 H10 0.95 .
C11 N2 1.375(5) .
C11 H11 0.95 .
C12 N1 1.449(5) .
C12 H12A 0.98 .
C12 H12B 0.98 .
C12 H12C 0.98 .
C13 N2 1.464(4) .
C13 C14 1.501(6) .
C13 H13A 0.99 .
C13 H13B 0.99 .
C14 N3 1.460(5) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C15 N3 1.464(6) .
C15 H15A 0.98 .
C15 H15B 0.98 .
C15 H15C 0.98 .
C16 N3 1.453(6) .
C16 H16A 0.98 .
C16 H16B 0.98 .
C16 H16C 0.98 .
S1 Fe2 2.2595(10) .
S1 Fe1 2.2632(11) .
S2 Fe2 2.2631(10) .
S2 Fe1 2.2691(10) .
Fe1 Fe2 2.5352(7) .
C17 C18 1.368(15) .
C17 O6 1.41(3) 2_967
C17 C18 1.916(18) 2_967
C17 H10A 0.99 .
C17 H10B 0.99 .
C18 O6 1.25(3) .
C18 C17 1.916(18) 2_967
C18 H10C 0.99 .
C18 H10D 0.99 .
O6 C17 1.41(3) 2_967
