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#$Date: 2016-03-25 14:54:30 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179905 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/01/7020181.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_7020181
loop_
_publ_author_name
'Deng, Hai-ning'
'Xing, Ya-lin'
'Xia, Cong-liang'
'Sun, Hong-mei'
'Shen, Qi'
'Zhang, Yong'
_publ_section_title
;
 Ionic iron(III) complexes of bis(phenol)-functionalized imidazolium
 cations: synthesis, structures and catalysis for aryl Grignard
 cross-coupling of alkyl halides.
;
_journal_issue                   38
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11597
_journal_page_last               11607
_journal_paper_doi               10.1039/c2dt30931a
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C33 H49 Cl4 Fe N2 O2'
_chemical_formula_sum            'C33 H49 Cl4 Fe N2 O2'
_chemical_formula_weight         703.39
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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                 110.727(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.221(10)
_cell_length_b                   22.283(10)
_cell_length_c                   9.501(5)
_cell_measurement_reflns_used    7904
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     3608(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9524
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_correction_T_min  0.445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4087
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0762
_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)+(0.1080P)²+0.6384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.2218
_reflns_number_gt                2503
_reflns_number_total             4087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30931a.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7020181
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.5000 0.32541(4) 0.2500 0.0519(3) Uani 1 2 d S . .
Cl1 Cl 0.56564(8) 0.26935(6) 0.14688(17) 0.0688(4) Uani 1 1 d . . .
Cl2 Cl 0.41984(9) 0.38488(6) 0.07954(17) 0.0759(5) Uani 1 1 d . . .
O1 O 0.6873(2) 0.48400(14) -0.1713(4) 0.0529(9) Uani 1 1 d . . .
H1A H 0.711(3) 0.501(3) -0.201(6) 0.064 Uiso 1 1 d . . .
N1 N 0.54639(19) 0.42605(14) -0.1406(3) 0.0373(7) Uani 1 1 d . . .
C1 C 0.5000 0.4604(2) -0.2500 0.0388(12) Uani 1 2 d S . .
H1 H 0.5000 0.5026 -0.2500 0.047 Uiso 1 2 calc SR . .
C2 C 0.5287(3) 0.36745(19) -0.1821(5) 0.0527(11) Uani 1 1 d . . .
H2 H 0.5525 0.3334 -0.1258 0.063 Uiso 1 1 calc R . .
C3 C 0.6055(2) 0.44638(18) 0.0017(4) 0.0413(9) Uani 1 1 d . . .
H3A H 0.5896 0.4341 0.0857 0.050 Uiso 1 1 calc R . .
H3B H 0.6084 0.4903 0.0019 0.050 Uiso 1 1 calc R . .
C4 C 0.6856(2) 0.42058(16) 0.0236(4) 0.0348(8) Uani 1 1 d . . .
C5 C 0.7262(2) 0.44041(16) -0.0678(4) 0.0365(8) Uani 1 1 d . . .
C6 C 0.7990(2) 0.41665(16) -0.0549(4) 0.0385(9) Uani 1 1 d . . .
C7 C 0.8296(2) 0.37274(16) 0.0567(5) 0.0412(9) Uani 1 1 d . . .
H7 H 0.8789 0.3563 0.0680 0.049 Uiso 1 1 calc R . .
C8 C 0.7919(2) 0.35204(17) 0.1513(4) 0.0392(9) Uani 1 1 d . A .
C9 C 0.7187(2) 0.37639(17) 0.1321(4) 0.0394(9) Uani 1 1 d . . .
H9 H 0.6910 0.3629 0.1928 0.047 Uiso 1 1 calc R . .
C10 C 0.8428(3) 0.4356(2) -0.1599(5) 0.0519(11) Uani 1 1 d . . .
C11 C 0.8633(3) 0.5029(2) -0.1441(6) 0.0604(13) Uani 1 1 d . . .
H11A H 0.8155 0.5263 -0.1685 0.091 Uiso 1 1 calc R . .
H11B H 0.8902 0.5135 -0.2125 0.091 Uiso 1 1 calc R . .
H11C H 0.8972 0.5114 -0.0415 0.091 Uiso 1 1 calc R . .
C12 C 0.9217(4) 0.4033(3) -0.1226(8) 0.087(2) Uani 1 1 d . . .
H12A H 0.9524 0.4085 -0.0167 0.130 Uiso 1 1 calc R . .
H12B H 0.9500 0.4202 -0.1827 0.130 Uiso 1 1 calc R . .
H12C H 0.9127 0.3609 -0.1449 0.130 Uiso 1 1 calc R . .
C13 C 0.7916(4) 0.4210(3) -0.3248(6) 0.0812(18) Uani 1 1 d . . .
H13A H 0.7803 0.3784 -0.3345 0.122 Uiso 1 1 calc R . .
H13B H 0.8196 0.4322 -0.3907 0.122 Uiso 1 1 calc R . .
H13C H 0.7428 0.4433 -0.3524 0.122 Uiso 1 1 calc R . .
C14 C 0.8301(3) 0.30421(18) 0.2709(5) 0.0492(11) Uani 1 1 d D . .
C15 C 0.8495(10) 0.2496(4) 0.2062(15) 0.082(4) Uani 0.50 1 d PD A 1
H15A H 0.8803 0.2232 0.2866 0.123 Uiso 0.50 1 calc PR A 1
H15B H 0.8795 0.2599 0.1434 0.123 Uiso 0.50 1 calc PR A 1
H15C H 0.8015 0.2294 0.1458 0.123 Uiso 0.50 1 calc PR A 1
C16 C 0.9029(5) 0.3324(4) 0.3873(11) 0.061(3) Uani 0.50 1 d PD A 1
H16A H 0.9313 0.3021 0.4594 0.091 Uiso 0.50 1 calc PR A 1
H16B H 0.8871 0.3645 0.4394 0.091 Uiso 0.50 1 calc PR A 1
H16C H 0.9366 0.3484 0.3370 0.091 Uiso 0.50 1 calc PR A 1
C17 C 0.7789(6) 0.2901(5) 0.3658(12) 0.059(3) Uani 0.50 1 d PD A 1
H17A H 0.7337 0.2667 0.3064 0.089 Uiso 0.50 1 calc PR A 1
H17B H 0.7614 0.3273 0.3966 0.089 Uiso 0.50 1 calc PR A 1
H17C H 0.8095 0.2674 0.4543 0.089 Uiso 0.50 1 calc PR A 1
C15' C 0.7906(8) 0.2438(4) 0.2111(16) 0.085(4) Uani 0.50 1 d PD A 2
H15D H 0.7889 0.2380 0.1088 0.128 Uiso 0.50 1 calc PR A 2
H15E H 0.7376 0.2438 0.2124 0.128 Uiso 0.50 1 calc PR A 2
H15F H 0.8204 0.2116 0.2744 0.128 Uiso 0.50 1 calc PR A 2
C16' C 0.9150(5) 0.2913(6) 0.2810(14) 0.078(3) Uani 0.50 1 d PD A 2
H16D H 0.9387 0.2624 0.3606 0.117 Uiso 0.50 1 calc PR A 2
H16E H 0.9451 0.3282 0.3029 0.117 Uiso 0.50 1 calc PR A 2
H16F H 0.9145 0.2751 0.1860 0.117 Uiso 0.50 1 calc PR A 2
C17' C 0.8296(13) 0.3193(7) 0.4210(11) 0.112(7) Uani 0.50 1 d PD A 2
H17D H 0.7961 0.3539 0.4138 0.167 Uiso 0.50 1 calc PR A 2
H17E H 0.8825 0.3284 0.4874 0.167 Uiso 0.50 1 calc PR A 2
H17F H 0.8097 0.2854 0.4608 0.167 Uiso 0.50 1 calc PR A 2
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'
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
Cl1 Fe1 Cl1 110.31(9) . 2_655
Cl1 Fe1 Cl2 110.38(7) . 2_655
Cl1 Fe1 Cl2 109.89(7) 2_655 2_655
Cl1 Fe1 Cl2 109.89(7) . .
Cl1 Fe1 Cl2 110.38(7) 2_655 .
Cl2 Fe1 Cl2 105.91(9) 2_655 .
C5 O1 H1A 116(5) . .
C1 N1 C2 107.8(3) . .
C1 N1 C3 126.8(3) . .
C2 N1 C3 125.4(3) . .
N1 C1 N1 109.4(5) . 2_654
N1 C1 H1 125.3 . .
N1 C1 H1 125.3 2_654 .
C2 C2 N1 107.5(2) 2_654 .
C2 C2 H2 126.3 2_654 .
N1 C2 H2 126.3 . .
N1 C3 C4 111.5(3) . .
N1 C3 H3A 109.3 . .
C4 C3 H3A 109.3 . .
N1 C3 H3B 109.3 . .
C4 C3 H3B 109.3 . .
H3A C3 H3B 108.0 . .
C5 C4 C9 119.7(4) . .
C5 C4 C3 119.5(3) . .
C9 C4 C3 120.8(3) . .
O1 C5 C6 124.2(3) . .
O1 C5 C4 114.3(3) . .
C6 C5 C4 121.5(3) . .
C5 C6 C7 116.3(4) . .
C5 C6 C10 122.3(4) . .
C7 C6 C10 121.4(4) . .
C8 C7 C6 124.3(4) . .
C8 C7 H7 117.8 . .
C6 C7 H7 117.8 . .
C9 C8 C7 117.1(4) . .
C9 C8 C14 122.0(4) . .
C7 C8 C14 120.8(4) . .
C8 C9 C4 121.0(4) . .
C8 C9 H9 119.5 . .
C4 C9 H9 119.5 . .
C12 C10 C11 105.0(4) . .
C12 C10 C6 112.4(4) . .
C11 C10 C6 111.5(4) . .
C12 C10 C13 108.4(5) . .
C11 C10 C13 109.9(4) . .
C6 C10 C13 109.4(4) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 C17' 133.1(7) . .
C15 C14 C16 111.6(9) . .
C17' C14 C16 60.4(10) . .
C15 C14 C8 112.4(6) . .
C17' C14 C8 113.8(6) . .
C16 C14 C8 107.5(5) . .
C15 C14 C15' 42.8(7) . .
C17' C14 C15' 113.3(11) . .
C16 C14 C15' 143.1(7) . .
C8 C14 C15' 107.8(6) . .
C15 C14 C17 111.2(8) . .
C17' C14 C17 42.7(8) . .
C16 C14 C17 102.1(7) . .
C8 C14 C17 111.5(5) . .
C15' C14 C17 74.8(9) . .
C15 C14 C16' 59.0(8) . .
C17' C14 C16' 109.4(10) . .
C16 C14 C16' 55.7(7) . .
C8 C14 C16' 110.9(5) . .
C15' C14 C16' 100.8(8) . .
C17 C14 C16' 136.5(6) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
C14 C17 H17A 109.5 . .
C14 C17 H17B 109.5 . .
C14 C17 H17C 109.5 . .
C14 C15' H15D 109.5 . .
C14 C15' H15E 109.5 . .
H15D C15' H15E 109.5 . .
C14 C15' H15F 109.5 . .
H15D C15' H15F 109.5 . .
H15E C15' H15F 109.5 . .
C14 C16' H16D 109.5 . .
C14 C16' H16E 109.5 . .
H16D C16' H16E 109.5 . .
C14 C16' H16F 109.5 . .
H16D C16' H16F 109.5 . .
H16E C16' H16F 109.5 . .
C14 C17' H17D 109.5 . .
C14 C17' H17E 109.5 . .
H17D C17' H17E 109.5 . .
C14 C17' H17F 109.5 . .
H17D C17' H17F 109.5 . .
H17E C17' H17F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 Cl1 2.1864(15) .
Fe1 Cl1 2.1864(15) 2_655
Fe1 Cl2 2.1995(16) 2_655
Fe1 Cl2 2.1995(16) .
O1 C5 1.386(5) .
O1 H1A 0.70(5) .
N1 C1 1.327(4) .
N1 C2 1.369(5) .
N1 C3 1.471(5) .
C1 N1 1.327(4) 2_654
C1 H1 0.9400 .
C2 C2 1.344(9) 2_654
C2 H2 0.9400 .
C3 C4 1.512(5) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C4 C5 1.398(5) .
C4 C9 1.398(5) .
C5 C6 1.392(6) .
C6 C7 1.405(5) .
C6 C10 1.541(6) .
C7 C8 1.390(6) .
C7 H7 0.9400 .
C8 C9 1.392(6) .
C8 C14 1.533(5) .
C9 H9 0.9400 .
C10 C12 1.532(7) .
C10 C11 1.541(6) .
C10 C13 1.548(7) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 H11C 0.9700 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 H12C 0.9700 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 H13C 0.9700 .
C14 C15 1.462(8) .
C14 C17' 1.468(8) .
C14 C16 1.530(8) .
C14 C15' 1.536(8) .
C14 C17 1.541(8) .
C14 C16' 1.543(8) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 H15C 0.9700 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 H16C 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 H17C 0.9700 .
C15' H15D 0.9700 .
C15' H15E 0.9700 .
C15' H15F 0.9700 .
C16' H16D 0.9700 .
C16' H16E 0.9700 .
C16' H16F 0.9700 .
C17' H17D 0.9700 .
C17' H17E 0.9700 .
C17' H17F 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
O1 H1A C11 0.70(5) 2.64(6) 3.154(6) 132(6)
O1 H1A C13 0.70(5) 2.82(6) 3.110(7) 108(5)
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
_geom_torsion_site_symmetry_4
C2 N1 C1 N1 0.0(2) 2_654
C3 N1 C1 N1 -179.1(4) 2_654
C1 N1 C2 C2 0.1(6) 2_654
C3 N1 C2 C2 179.2(4) 2_654
C1 N1 C3 C4 -124.7(3) .
C2 N1 C3 C4 56.5(5) .
N1 C3 C4 C5 70.0(5) .
N1 C3 C4 C9 -108.8(4) .
C9 C4 C5 O1 179.7(3) .
C3 C4 C5 O1 0.9(5) .
C9 C4 C5 C6 0.8(6) .
C3 C4 C5 C6 -178.0(3) .
O1 C5 C6 C7 180.0(4) .
C4 C5 C6 C7 -1.3(6) .
O1 C5 C6 C10 -1.9(6) .
C4 C5 C6 C10 176.8(4) .
C5 C6 C7 C8 0.5(6) .
C10 C6 C7 C8 -177.6(4) .
C6 C7 C8 C9 0.7(6) .
C6 C7 C8 C14 -179.6(4) .
C7 C8 C9 C4 -1.2(6) .
C14 C8 C9 C4 179.1(4) .
C5 C4 C9 C8 0.5(6) .
C3 C4 C9 C8 179.2(3) .
C5 C6 C10 C12 179.7(4) .
C7 C6 C10 C12 -2.3(6) .
C5 C6 C10 C11 62.1(6) .
C7 C6 C10 C11 -119.9(4) .
C5 C6 C10 C13 -59.8(5) .
C7 C6 C10 C13 118.2(5) .
C9 C8 C14 C15 123.3(8) .
C7 C8 C14 C15 -56.4(9) .
C9 C8 C14 C17' -48.8(11) .
C7 C8 C14 C17' 131.5(11) .
C9 C8 C14 C16 -113.5(6) .
C7 C8 C14 C16 66.8(7) .
C9 C8 C14 C15' 77.8(8) .
C7 C8 C14 C15' -101.9(8) .
C9 C8 C14 C17 -2.4(7) .
C7 C8 C14 C17 177.9(6) .
C9 C8 C14 C16' -172.7(7) .
C7 C8 C14 C16' 7.6(7) .
