#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:44:48 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179762 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/58/7005870.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_7005870
loop_
_publ_author_name
'Wang, Fujun'
'Wang, Mei'
'Liu, Xiaoyang'
'Jin, Kun'
'Dong, Weibing'
'Sun, Licheng'
_publ_section_title
;
 Protonation, electrochemical properties and molecular structures of
 halogen-functionalized diiron azadithiolate complexes related to the
 active site of iron-only hydrogenases.
;
_journal_issue                   34
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3812
_journal_page_last               3819
_journal_paper_doi               10.1039/b706178a
_journal_year                    2007
_chemical_formula_moiety         'C15 H11 Br Cl Fe2 N O10 S2'
_chemical_formula_sum            'C15 H11 Br Cl Fe2 N O10 S2'
_chemical_formula_weight         656.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             'Aug 15 14:01:24 2004'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.63(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.953(10)
_cell_length_b                   6.611(3)
_cell_length_c                   15.033(6)
_cell_measurement_temperature    273(2)
_cell_volume                     2207.2(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_detector       'Imaging Plate'
_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  0.2544
_diffrn_reflns_av_sigmaI/netI    0.2231
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14151
_diffrn_reflns_theta_full        28.82
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.488
_exptl_absorpt_correction_T_max  0.572
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'black red'
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.2075
_refine_ls_R_factor_gt           0.0865
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0699P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1947
_reflns_number_gt                2403
_reflns_number_total             5515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b706178a.txt
_cod_data_source_block           1NH
_cod_original_cell_volume        2207.2(16)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7005870
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2035(2) 0.0113(11) 0.3208(4) 0.0267(16) Uani 1 1 d . . .
H1 H 0.2093 0.0631 0.3785 0.080 Uiso 1 1 calc . . .
Cl1 Cl 0.16705(9) -0.3377(4) 0.06221(15) 0.0388(6) Uani 1 1 d . . .
Fe1 Fe 0.36801(5) -0.0032(2) 0.30550(9) 0.0344(4) Uani 1 1 d . . .
Fe2 Fe 0.34667(5) 0.12214(19) 0.45080(9) 0.0303(3) Uani 1 1 d . . .
Br1 Br 0.12671(5) 0.35784(19) 0.40548(8) 0.0577(4) Uani 1 1 d . . .
S1 S 0.31625(8) -0.1801(3) 0.38682(15) 0.0297(5) Uani 1 1 d . . .
S2 S 0.30221(8) 0.2453(3) 0.31000(16) 0.0298(5) Uani 1 1 d . . .
O1 O 0.4448(4) 0.3079(16) 0.2569(8) 0.100(4) Uani 1 1 d . . .
O2 O 0.4729(3) -0.2608(14) 0.3712(7) 0.092(3) Uani 1 1 d . . .
O3 O 0.3265(3) -0.1967(17) 0.1243(6) 0.094(3) Uani 1 1 d . . .
O4 O 0.4389(3) -0.0983(12) 0.5854(6) 0.075(3) Uani 1 1 d . . .
O5 O 0.2742(3) 0.2562(15) 0.5736(6) 0.080(3) Uani 1 1 d . . .
O6 O 0.4246(3) 0.4750(12) 0.4880(6) 0.072(3) Uani 1 1 d . . .
O7 O 0.1052(3) -0.3471(14) 0.0164(6) 0.081(3) Uani 1 1 d . . .
O8 O 0.2012(3) -0.3919(13) 0.0003(5) 0.065(2) Uani 1 1 d . . .
O9 O 0.1812(4) -0.4649(14) 0.1395(5) 0.082(3) Uani 1 1 d . . .
O10 O 0.1825(3) -0.1337(11) 0.0940(6) 0.066(2) Uani 1 1 d . . .
C1 C 0.4166(4) 0.193(2) 0.2765(8) 0.059(3) Uani 1 1 d . . .
C2 C 0.4312(4) -0.1616(18) 0.3458(8) 0.053(3) Uani 1 1 d . . .
C3 C 0.3420(4) -0.1157(16) 0.1949(7) 0.044(3) Uani 1 1 d . . .
C4 C 0.4021(4) -0.0141(18) 0.5336(8) 0.054(3) Uani 1 1 d . . .
C5 C 0.3002(4) 0.1989(17) 0.5258(7) 0.045(3) Uani 1 1 d . . .
C6 C 0.3936(4) 0.3416(18) 0.4712(7) 0.048(3) Uani 1 1 d . . .
C7 C 0.0867(4) 0.3059(16) 0.2809(7) 0.044(3) Uani 1 1 d . . .
C8 C 0.0971(3) 0.1317(14) 0.2396(6) 0.032(2) Uani 1 1 d . . .
C9 C 0.0662(3) 0.1067(15) 0.1413(8) 0.047(3) Uani 1 1 d . . .
H9 H 0.0726 -0.0080 0.1092 0.080 Uiso 1 1 calc . . .
C10 C 0.0282(4) 0.255(2) 0.0987(7) 0.056(3) Uani 1 1 d . . .
H8 H 0.0089 0.2427 0.0367 0.080 Uiso 1 1 calc . . .
C11 C 0.0180(4) 0.4219(17) 0.1457(8) 0.051(3) Uani 1 1 d . . .
H7 H -0.0093 0.5188 0.1156 0.080 Uiso 1 1 calc . . .
C12 C 0.0469(4) 0.4500(15) 0.2359(8) 0.049(3) Uani 1 1 d . . .
H6 H 0.0397 0.5657 0.2667 0.080 Uiso 1 1 calc . . .
C13 C 0.1361(3) -0.0394(13) 0.2847(6) 0.031(2) Uani 1 1 d . . .
H3A H 0.1321 -0.1493 0.2408 0.080 Uiso 1 1 calc . . .
H3B H 0.1212 -0.0876 0.3357 0.080 Uiso 1 1 calc . . .
C14 C 0.2366(3) -0.1905(12) 0.3284(6) 0.0245(18) Uani 1 1 d . . .
H1A H 0.2325 -0.2435 0.2670 0.080 Uiso 1 1 calc . . .
H1B H 0.2171 -0.2851 0.3609 0.080 Uiso 1 1 calc . . .
C15 C 0.2254(3) 0.1588(15) 0.2650(6) 0.034(2) Uani 1 1 d . . .
H2A H 0.1991 0.2757 0.2567 0.080 Uiso 1 1 calc . . .
H2B H 0.2222 0.1003 0.2048 0.080 Uiso 1 1 calc . . .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C15 N1 C14 113.1(6) . . ?
C15 N1 C13 113.8(6) . . ?
C14 N1 C13 105.8(6) . . ?
C15 N1 H1 108.0 . . ?
C14 N1 H1 108.0 . . ?
C13 N1 H1 108.0 . . ?
O9 Cl1 O8 110.1(5) . . ?
O9 Cl1 O7 111.8(5) . . ?
O8 Cl1 O7 109.0(5) . . ?
O9 Cl1 O10 107.4(5) . . ?
O8 Cl1 O10 109.0(5) . . ?
O7 Cl1 O10 109.5(5) . . ?
C2 Fe1 C3 97.2(5) . . ?
C2 Fe1 C1 90.3(5) . . ?
C3 Fe1 C1 98.8(5) . . ?
C2 Fe1 S1 90.3(3) . . ?
C3 Fe1 S1 101.1(3) . . ?
C1 Fe1 S1 159.8(4) . . ?
C2 Fe1 S2 157.5(4) . . ?
C3 Fe1 S2 105.3(3) . . ?
C1 Fe1 S2 86.8(4) . . ?
S1 Fe1 S2 84.95(9) . . ?
C2 Fe1 Fe2 102.8(4) . . ?
C3 Fe1 Fe2 149.4(3) . . ?
C1 Fe1 Fe2 103.8(4) . . ?
S1 Fe1 Fe2 56.44(7) . . ?
S2 Fe1 Fe2 56.54(7) . . ?
C4 Fe2 C6 89.8(4) . . ?
C4 Fe2 C5 97.8(5) . . ?
C6 Fe2 C5 95.2(5) . . ?
C4 Fe2 S1 86.5(3) . . ?
C6 Fe2 S1 154.5(4) . . ?
C5 Fe2 S1 110.3(3) . . ?
C4 Fe2 S2 155.6(4) . . ?
C6 Fe2 S2 88.8(3) . . ?
C5 Fe2 S2 106.6(3) . . ?
S1 Fe2 S2 84.35(9) . . ?
C4 Fe2 Fe1 100.4(4) . . ?
C6 Fe2 Fe1 100.2(4) . . ?
C5 Fe2 Fe1 156.2(3) . . ?
S1 Fe2 Fe1 55.93(7) . . ?
S2 Fe2 Fe1 56.06(7) . . ?
C14 S1 Fe1 111.3(3) . . ?
C14 S1 Fe2 113.9(3) . . ?
Fe1 S1 Fe2 67.63(8) . . ?
C15 S2 Fe1 110.9(3) . . ?
C15 S2 Fe2 113.7(3) . . ?
Fe1 S2 Fe2 67.41(8) . . ?
O1 C1 Fe1 178.2(12) . . ?
O2 C2 Fe1 178.4(10) . . ?
O3 C3 Fe1 176.9(10) . . ?
O4 C4 Fe2 177.8(10) . . ?
O5 C5 Fe2 175.4(10) . . ?
O6 C6 Fe2 176.5(9) . . ?
C8 C7 C12 122.3(9) . . ?
C8 C7 Br1 120.5(7) . . ?
C12 C7 Br1 117.2(8) . . ?
C7 C8 C9 117.2(8) . . ?
C7 C8 C13 126.1(8) . . ?
C9 C8 C13 116.7(8) . . ?
C10 C9 C8 118.5(10) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 121.0(10) . . ?
C11 C10 H8 119.5 . . ?
C9 C10 H8 119.5 . . ?
C10 C11 C12 121.5(9) . . ?
C10 C11 H7 119.3 . . ?
C12 C11 H7 119.3 . . ?
C11 C12 C7 119.5(10) . . ?
C11 C12 H6 120.3 . . ?
C7 C12 H6 120.3 . . ?
C8 C13 N1 115.4(7) . . ?
C8 C13 H3A 108.4 . . ?
N1 C13 H3A 108.4 . . ?
C8 C13 H3B 108.4 . . ?
N1 C13 H3B 108.4 . . ?
H3A C13 H3B 107.5 . . ?
N1 C14 S1 115.1(5) . . ?
N1 C14 H1A 108.5 . . ?
S1 C14 H1A 108.5 . . ?
N1 C14 H1B 108.5 . . ?
S1 C14 H1B 108.5 . . ?
H1A C14 H1B 107.5 . . ?
N1 C15 S2 116.2(5) . . ?
N1 C15 H2A 108.2 . . ?
S2 C15 H2A 108.2 . . ?
N1 C15 H2B 108.2 . . ?
S2 C15 H2B 108.2 . . ?
H2A C15 H2B 107.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C15 1.456(11) . ?
N1 C14 1.525(10) . ?
N1 C13 1.542(9) . ?
N1 H1 0.9100 . ?
Cl1 O9 1.404(8) . ?
Cl1 O8 1.405(7) . ?
Cl1 O7 1.414(6) . ?
Cl1 O10 1.445(7) . ?
Fe1 C2 1.767(11) . ?
Fe1 C3 1.781(10) . ?
Fe1 C1 1.831(13) . ?
Fe1 S1 2.237(3) . ?
Fe1 S2 2.244(3) . ?
Fe1 Fe2 2.498(2) . ?
Fe2 C4 1.782(11) . ?
Fe2 C6 1.787(11) . ?
Fe2 C5 1.810(11) . ?
Fe2 S1 2.251(3) . ?
Fe2 S2 2.257(3) . ?
Br1 C7 1.897(10) . ?
S1 C14 1.819(7) . ?
S2 C15 1.813(8) . ?
O1 C1 1.089(13) . ?
O2 C2 1.144(11) . ?
O3 C3 1.162(11) . ?
O4 C4 1.140(11) . ?
O5 C5 1.110(12) . ?
O6 C6 1.120(11) . ?
C7 C8 1.358(13) . ?
C7 C12 1.375(13) . ?
C8 C9 1.478(13) . ?
C8 C13 1.495(11) . ?
C9 C10 1.362(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.360(16) . ?
C10 H8 0.9300 . ?
C11 C12 1.363(14) . ?
C11 H7 0.9300 . ?
C12 H6 0.9300 . ?
C13 H3A 0.9700 . ?
C13 H3B 0.9700 . ?
C14 H1A 0.9700 . ?
C14 H1B 0.9700 . ?
C15 H2A 0.9700 . ?
C15 H2B 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O8 0.91 2.20 2.826(9) 125.2 4_556
N1 H1 Br1 0.91 2.82 3.334(7) 117.2 .
