#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:56:26 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179400 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/97/4329782.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_4329782
loop_
_publ_author_name
'Li-Cheng Song'
'Zhao-Jun Xie'
'Miao-Miao Wang'
'Gao-Yu Zhao'
'Hai-Bin Song'
_publ_section_title
;
 Biomimetic Models for the Active Site of [Fe]Hydrogenase Featuring an
 Acylmethyl(hydroxymethyl)pyridine Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7466
_journal_page_last               7468
_journal_paper_doi               10.1021/ic301146u
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C21 H18 Cl2 Fe2 I2 N2 O8'
_chemical_formula_weight         862.77
_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                 118.86(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.10(3)
_cell_length_b                   8.697(8)
_cell_length_c                   13.528(14)
_cell_measurement_reflns_used    5176
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.7
_cell_volume                     2792(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17005
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.487
_exptl_absorpt_correction_T_max  0.6797
_exptl_absorpt_correction_T_min  0.5423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.052
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.795
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0281
_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)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0575
_reflns_number_gt                2575
_reflns_number_total             3324
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301146u_si_003_2.cif
_cod_data_source_block           m110628b1-3
_cod_original_cell_volume        2793(5)
_cod_database_code               4329782
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
I1 I 0.209898(9) 0.43471(2) 0.263406(15) 0.02473(7) Uani 1 1 d .
Fe1 Fe 0.106403(18) 0.53388(4) 0.20099(3) 0.01758(10) Uani 1 1 d .
O1 O -0.01295(10) 0.5833(3) 0.12677(18) 0.0364(6) Uani 1 1 d .
O2 O 0.07309(10) 0.2274(2) 0.10173(17) 0.0382(6) Uani 1 1 d .
O3 O 0.09915(9) 0.3426(2) 0.36603(15) 0.0237(5) Uani 1 1 d .
O4 O 0.10463(10) 0.6833(2) 0.07243(16) 0.0267(5) Uani 1 1 d D
N1 N 0.13748(9) 0.7280(3) 0.28153(18) 0.0170(5) Uani 1 1 d .
C1 C 0.03429(14) 0.5724(3) 0.1570(2) 0.0237(7) Uani 1 1 d .
C2 C 0.08655(13) 0.3481(3) 0.1393(2) 0.0244(7) Uani 1 1 d .
C3 C 0.11498(13) 0.4623(3) 0.3427(2) 0.0196(6) Uani 1 1 d .
C4 C 0.14660(13) 0.5801(3) 0.4375(2) 0.0241(7) Uani 1 1 d .
H4A H 0.1252 0.5974 0.4786 0.029 Uiso 1 1 calc R
H4B H 0.1839 0.5376 0.4917 0.029 Uiso 1 1 calc R
C5 C 0.15471(12) 0.7300(3) 0.3940(2) 0.0196(6) Uani 1 1 d .
C6 C 0.17847(12) 0.8610(3) 0.4576(2) 0.0239(7) Uani 1 1 d .
H6 H 0.1905 0.8620 0.5362 0.029 Uiso 1 1 calc R
C7 C 0.18449(14) 0.9908(3) 0.4047(3) 0.0295(8) Uani 1 1 d .
H7 H 0.2003 1.0821 0.4468 0.035 Uiso 1 1 calc R
C8 C 0.16742(13) 0.9868(3) 0.2901(3) 0.0246(7) Uani 1 1 d .
H8 H 0.1716 1.0747 0.2531 0.030 Uiso 1 1 calc R
C9 C 0.14415(12) 0.8525(3) 0.2306(2) 0.0186(6) Uani 1 1 d .
C10 C 0.12739(14) 0.8324(3) 0.1084(2) 0.0289(8) Uani 1 1 d .
H10A H 0.0990 0.9108 0.0628 0.035 Uiso 1 1 calc R
H10B H 0.1607 0.8463 0.0974 0.035 Uiso 1 1 calc R
Cl1 Cl -0.01136(5) -0.03845(12) 0.13342(8) 0.0575(3) Uani 1 1 d .
C11 C 0.0000 0.0759(5) 0.2500 0.0413(14) Uani 1 2 d S
H11A H -0.0332 0.1428 0.2289 0.050 Uiso 0.50 1 calc PR
H11B H 0.0332 0.1428 0.2711 0.050 Uiso 0.50 1 calc PR
H4 H 0.1022(13) 0.657(3) 0.0100(14) 0.032(9) Uiso 1 1 d 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'
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'
I I -0.4742 1.8119 '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
C2 Fe1 C1 88.81(14) . .
C2 Fe1 C3 92.15(13) . .
C1 Fe1 C3 88.78(13) . .
C2 Fe1 N1 172.93(12) . .
C1 Fe1 N1 97.55(12) . .
C3 Fe1 N1 84.95(12) . .
C2 Fe1 O4 106.59(12) . .
C1 Fe1 O4 91.37(11) . .
C3 Fe1 O4 161.26(10) . .
N1 Fe1 O4 76.45(11) . .
C2 Fe1 I1 83.57(11) . .
C1 Fe1 I1 171.87(9) . .
C3 Fe1 I1 88.67(10) . .
N1 Fe1 I1 89.91(8) . .
O4 Fe1 I1 93.52(7) . .
C10 O4 Fe1 116.00(16) . .
C10 O4 H4 113(2) . .
Fe1 O4 H4 127(2) . .
C9 N1 C5 120.4(2) . .
C9 N1 Fe1 122.43(19) . .
C5 N1 Fe1 117.10(18) . .
O1 C1 Fe1 173.8(3) . .
O2 C2 Fe1 177.9(3) . .
O3 C3 C4 118.4(2) . .
O3 C3 Fe1 130.1(2) . .
C4 C3 Fe1 111.5(2) . .
C5 C4 C3 112.5(2) . .
C5 C4 H4A 109.1 . .
C3 C4 H4A 109.1 . .
C5 C4 H4B 109.1 . .
C3 C4 H4B 109.1 . .
H4A C4 H4B 107.8 . .
N1 C5 C6 120.8(3) . .
N1 C5 C4 113.2(2) . .
C6 C5 C4 126.0(3) . .
C5 C6 C7 118.9(3) . .
C5 C6 H6 120.5 . .
C7 C6 H6 120.5 . .
C8 C7 C6 119.8(3) . .
C8 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
C9 C8 C7 118.9(3) . .
C9 C8 H8 120.6 . .
C7 C8 H8 120.6 . .
N1 C9 C8 121.2(3) . .
N1 C9 C10 115.4(2) . .
C8 C9 C10 123.4(3) . .
O4 C10 C9 109.6(2) . .
O4 C10 H10A 109.7 . .
C9 C10 H10A 109.7 . .
O4 C10 H10B 109.7 . .
C9 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
Cl1 C11 Cl1 111.3(3) . 2
Cl1 C11 H11A 109.4 . .
Cl1 C11 H11A 109.4 2 .
Cl1 C11 H11B 109.4 . .
Cl1 C11 H11B 109.4 2 .
H11A C11 H11B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Fe1 2.653(3) .
Fe1 C2 1.779(3) .
Fe1 C1 1.779(4) .
Fe1 C3 1.921(3) .
Fe1 N1 1.965(3) .
Fe1 O4 2.153(3) .
O1 C1 1.145(4) .
O2 C2 1.146(3) .
O3 C3 1.224(3) .
O4 C10 1.417(3) .
O4 H4 0.845(10) .
N1 C9 1.342(3) .
N1 C5 1.359(3) .
C3 C4 1.539(4) .
C4 C5 1.490(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.385(4) .
C6 C7 1.388(4) .
C6 H6 0.9500 .
C7 C8 1.387(4) .
C7 H7 0.9500 .
C8 C9 1.386(4) .
C8 H8 0.9500 .
C9 C10 1.498(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
Cl1 C11 1.761(3) .
C11 Cl1 1.761(3) 2
C11 H11A 0.9900 .
C11 H11B 0.9900 .
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
O4 H4 O3 0.845(10) 1.909(13) 2.733(4) 165(3) 6_565
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
C2 Fe1 O4 C10 -170.7(2)
C1 Fe1 O4 C10 100.1(2)
C3 Fe1 O4 C10 9.9(5)
N1 Fe1 O4 C10 2.7(2)
I1 Fe1 O4 C10 -86.4(2)
C2 Fe1 N1 C9 115.5(9)
C1 Fe1 N1 C9 -90.3(2)
C3 Fe1 N1 C9 -178.4(2)
O4 Fe1 N1 C9 -0.7(2)
I1 Fe1 N1 C9 92.9(2)
C2 Fe1 N1 C5 -61.5(10)
C1 Fe1 N1 C5 92.6(2)
C3 Fe1 N1 C5 4.5(2)
O4 Fe1 N1 C5 -177.8(2)
I1 Fe1 N1 C5 -84.1(2)
C2 Fe1 C1 O1 12(2)
C3 Fe1 C1 O1 -80(2)
N1 Fe1 C1 O1 -164(2)
O4 Fe1 C1 O1 119(2)
I1 Fe1 C1 O1 -8(3)
C1 Fe1 C2 O2 -60(9)
C3 Fe1 C2 O2 28(9)
N1 Fe1 C2 O2 94(9)
O4 Fe1 C2 O2 -151(9)
I1 Fe1 C2 O2 117(9)
C2 Fe1 C3 O3 -14.4(3)
C1 Fe1 C3 O3 74.4(3)
N1 Fe1 C3 O3 172.1(3)
O4 Fe1 C3 O3 165.1(2)
I1 Fe1 C3 O3 -97.9(3)
C2 Fe1 C3 C4 166.2(2)
C1 Fe1 C3 C4 -105.0(2)
N1 Fe1 C3 C4 -7.3(2)
O4 Fe1 C3 C4 -14.4(5)
I1 Fe1 C3 C4 82.7(2)
O3 C3 C4 C5 -170.3(3)
Fe1 C3 C4 C5 9.2(3)
C9 N1 C5 C6 1.2(4)
Fe1 N1 C5 C6 178.3(2)
C9 N1 C5 C4 -177.2(3)
Fe1 N1 C5 C4 -0.1(3)
C3 C4 C5 N1 -5.9(4)
C3 C4 C5 C6 175.8(3)
N1 C5 C6 C7 0.0(5)
C4 C5 C6 C7 178.2(3)
C5 C6 C7 C8 -0.8(5)
C6 C7 C8 C9 0.5(5)
C5 N1 C9 C8 -1.5(4)
Fe1 N1 C9 C8 -178.5(2)
C5 N1 C9 C10 175.7(3)
Fe1 N1 C9 C10 -1.2(4)
C7 C8 C9 N1 0.7(5)
C7 C8 C9 C10 -176.4(3)
Fe1 O4 C10 C9 -3.9(3)
N1 C9 C10 O4 3.3(4)
C8 C9 C10 O4 -179.5(3)
