#------------------------------------------------------------------------------
#$Date: 2018-08-16 02:29:15 +0100 (Thu, 16 Aug 2018) $
#$Revision: 209773 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/88/7108891.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_7108891
loop_
_publ_author_name
'Prodius, Denis'
'Macaev, Fliur'
'Stingaci, Eugenia'
'Pogrebnoi, Vsevolod'
'Mereacre, Valeriu'
'Novitchi, Ghenadie'
'Kostakis, George E.'
'Anson, Christopher E.'
'Powell, Annie K.'
_publ_section_title
;
 Catalytic "triangles": binding of iron in task-specific ionic liquids
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   19
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1915
_journal_page_last               1917
_journal_paper_doi               10.1039/c2cc36741f
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety
'(C36 H54 Fe3 N12 O16), 3(Cl4 Fe), 4(Cl), 7(H2 O)'
_chemical_formula_sum            'C36 H68 Cl16 Fe6 N12 O23'
_chemical_formula_weight         1939.32
_space_group_IT_number           190
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P -6c -2c'
_symmetry_space_group_name_H-M   'P -6 2 c'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            2
_cell_length_a                   13.3201(6)
_cell_length_b                   13.3201(6)
_cell_length_c                   24.7380(13)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.56
_cell_measurement_theta_min      1.95
_cell_volume                     3801.1(3)
_computing_cell_refinement       'IPDS 2.92 (Stoe & Cie GmbH, 1999)'
_computing_data_collection       'IPDS 2.92 (Stoe & Cie GmbH, 1999)'
_computing_data_reduction        'IPDS 2.92 (Stoe & Cie GmbH, 1999)'
_computing_molecular_graphics    'Diamond 2.1 (Crystal Impact, 1998)'
_computing_publication_material  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_structure_refinement  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_structure_solution    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 6.667
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'area detector'
_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  0.0869
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            29754
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    1.748
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.289
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0457
_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/[\s^2^(Fo^2^)+(0.0783P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                2153
_reflns_number_total             2588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36741f.txt
_cod_data_source_block           13acpyw
_cod_database_code               7108891
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z+1/2'
'-y, x-y, -z+1/2'
'-x+y, -x, -z+1/2'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, 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 0.09987(7) 0.16432(7) 0.2500 0.0258(2) Uani 1 2 d S . .
O1 O 0.0000 0.0000 0.2500 0.0272(15) Uani 1 6 d S . .
O2 O 0.2048(3) 0.1634(3) 0.30759(16) 0.0352(8) Uani 1 1 d . . .
O3 O 0.1857(3) -0.0132(3) 0.30776(15) 0.0341(8) Uani 1 1 d . . .
C1 C 0.2282(4) 0.0883(4) 0.3237(2) 0.0297(10) Uani 1 1 d . . .
C2 C 0.3191(5) 0.1305(5) 0.3670(2) 0.0431(13) Uani 1 1 d . . .
H2A H 0.3881 0.1984 0.3537 0.052 Uiso 1 1 calc R . .
H2B H 0.2913 0.1545 0.3979 0.052 Uiso 1 1 calc R . .
N1 N 0.3507(4) 0.0465(4) 0.38492(19) 0.0427(11) Uani 1 1 d . . .
C3 C 0.4416(5) 0.0431(5) 0.3677(3) 0.0452(14) Uani 1 1 d . . .
H3A H 0.4944 0.0930 0.3422 0.054 Uiso 1 1 calc R . .
N2 N 0.4464(4) -0.0435(4) 0.3924(2) 0.0483(13) Uani 1 1 d . . .
C4 C 0.3534(7) -0.0980(7) 0.4256(3) 0.0658(19) Uani 1 1 d . . .
H4A H 0.3347 -0.1618 0.4474 0.079 Uiso 1 1 calc R . .
C5 C 0.2930(7) -0.0413(7) 0.4208(3) 0.0665(19) Uani 1 1 d . . .
H5A H 0.2247 -0.0591 0.4388 0.080 Uiso 1 1 calc R . .
C6 C 0.5391(7) -0.0717(7) 0.3858(4) 0.072(2) Uani 1 1 d . . .
H6A H 0.5944 -0.0201 0.3598 0.108 Uiso 1 1 calc R . .
H6B H 0.5064 -0.1502 0.3734 0.108 Uiso 1 1 calc R . .
H6C H 0.5770 -0.0633 0.4199 0.108 Uiso 1 1 calc R . .
O4 O 0.2112(4) 0.3397(4) 0.2500 0.0463(14) Uani 1 2 d SD . .
H41 H 0.288(5) 0.367(9) 0.256(10) 0.069 Uiso 0.50 1 d PD . .
H42 H 0.187(9) 0.392(7) 0.2500 0.069 Uiso 1 2 d SD . .
O5 O 0.1667(7) 0.5086(7) 0.2500 0.098(4) Uani 1 2 d SD . .
H51 H 0.097(8) 0.510(15) 0.2500 0.147 Uiso 1 2 d SD . .
H52 H 0.208(13) 0.554(18) 0.280(6) 0.147 Uiso 0.50 1 d PD A -1
O6 O 0.4299(8) 0.1645(7) 0.2500 0.074(2) Uani 1 2 d SD . .
H61 H 0.477(7) 0.230(5) 0.2787(10) 0.112 Uiso 1 1 d D . .
Fe2 Fe 0.6667 0.3333 0.44040(5) 0.0421(3) Uani 1 3 d S . .
Cl1 Cl 0.6667 0.3333 0.35269(10) 0.0528(6) Uani 1 3 d S . .
Cl2 Cl 0.50470(13) 0.31716(14) 0.47034(6) 0.0543(4) Uani 1 1 d . . .
Fe3 Fe 0.0000 0.0000 0.5000 0.0484(5) Uani 1 6 d S . .
Cl3 Cl 0.0000 0.0000 0.40595(19) 0.0585(13) Uani 0.50 3 d SP . .
Cl4 Cl 0.1624(7) 0.1594(6) 0.5134(3) 0.102(3) Uani 0.50 1 d P . .
Cl11 Cl 0.4696(2) 0.4145(2) 0.2500 0.0659(7) Uani 1 2 d S . .
Cl12 Cl 0.3333 0.6667 0.3425(6) 0.088(4) Uani 0.50 3 d SPU B 1
O12 O 0.3333 0.6667 0.324(2) 0.095(6) Uani 0.50 3 d SPU C 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Fe1 0.0218(4) 0.0219(4) 0.0332(5) 0.000 0.000 0.0107(4)
O1 0.026(2) 0.026(2) 0.029(4) 0.000 0.000 0.0131(11)
O2 0.0329(18) 0.0260(16) 0.046(2) -0.0038(15) -0.0057(14) 0.0143(15)
O3 0.0336(17) 0.0289(17) 0.040(2) -0.0015(15) -0.0058(15) 0.0158(14)
C1 0.030(2) 0.030(2) 0.032(3) 0.0018(19) -0.0001(19) 0.0163(19)
C2 0.056(3) 0.041(3) 0.043(3) -0.012(2) -0.018(3) 0.032(3)
N1 0.050(3) 0.044(2) 0.035(3) -0.005(2) -0.017(2) 0.024(2)
C3 0.049(3) 0.039(3) 0.053(4) 0.007(3) -0.008(3) 0.026(3)
N2 0.055(3) 0.044(3) 0.052(3) -0.002(2) -0.014(2) 0.028(2)
C4 0.069(4) 0.067(4) 0.064(5) 0.021(4) -0.007(4) 0.036(4)
C5 0.066(4) 0.087(5) 0.051(4) 0.019(4) -0.001(3) 0.042(4)
C6 0.079(5) 0.078(5) 0.081(6) 0.007(4) -0.010(4) 0.056(4)
O4 0.028(2) 0.027(2) 0.075(4) 0.000 0.000 0.007(2)
O5 0.067(5) 0.054(5) 0.181(12) 0.000 0.000 0.036(4)
O6 0.092(6) 0.073(5) 0.069(5) 0.000 0.000 0.050(5)
Fe2 0.0468(5) 0.0468(5) 0.0329(7) 0.000 0.000 0.0234(2)
Cl1 0.0610(9) 0.0610(9) 0.0365(12) 0.000 0.000 0.0305(5)
Cl2 0.0488(8) 0.0719(10) 0.0446(8) -0.0095(7) -0.0033(6) 0.0320(8)
Fe3 0.0457(7) 0.0457(7) 0.0536(12) 0.000 0.000 0.0229(3)
Cl3 0.075(2) 0.075(2) 0.026(2) 0.000 0.000 0.0373(11)
Cl4 0.071(4) 0.071(4) 0.152(10) -0.049(5) -0.043(5) 0.0276(17)
Cl11 0.0429(11) 0.0493(12) 0.100(2) 0.000 0.000 0.0187(9)
Cl12 0.075(2) 0.075(2) 0.115(11) 0.000 0.000 0.0373(12)
O12 0.082(5) 0.082(5) 0.120(15) 0.000 0.000 0.041(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
O1 Fe1 O2 94.68(10) . .
O1 Fe1 O2 94.68(10) . 4
O2 Fe1 O2 90.9(2) . 4
O1 Fe1 O3 96.36(10) . 5
O2 Fe1 O3 168.94(14) . 5
O2 Fe1 O3 88.75(14) 4 5
O1 Fe1 O3 96.36(10) . 2
O2 Fe1 O3 88.75(14) . 2
O2 Fe1 O3 168.94(14) 4 2
O3 Fe1 O3 89.5(2) 5 2
O1 Fe1 O4 178.25(16) . .
O2 Fe1 O4 84.10(15) . .
O2 Fe1 O4 84.10(15) 4 .
O3 Fe1 O4 84.87(15) 5 .
O3 Fe1 O4 84.87(15) 2 .
Fe1 O1 Fe1 120.0 2 3
Fe1 O1 Fe1 120.0 2 .
Fe1 O1 Fe1 120.0 3 .
C1 O2 Fe1 133.2(3) . .
C1 O3 Fe1 130.1(3) . 3
O3 C1 O2 127.5(5) . .
O3 C1 C2 118.6(4) . .
O2 C1 C2 113.9(4) . .
N1 C2 C1 114.9(4) . .
N1 C2 H2A 108.5 . .
C1 C2 H2A 108.5 . .
N1 C2 H2B 108.5 . .
C1 C2 H2B 108.5 . .
H2A C2 H2B 107.5 . .
C3 N1 C5 108.6(5) . .
C3 N1 C2 124.0(5) . .
C5 N1 C2 127.4(6) . .
N1 C3 N2 109.0(6) . .
N1 C3 H3A 125.5 . .
N2 C3 H3A 125.5 . .
C3 N2 C4 108.3(5) . .
C3 N2 C6 125.4(6) . .
C4 N2 C6 126.2(6) . .
N2 C4 C5 106.6(6) . .
N2 C4 H4A 126.7 . .
C5 C4 H4A 126.7 . .
C4 C5 N1 107.4(7) . .
C4 C5 H5A 126.3 . .
N1 C5 H5A 126.3 . .
N2 C6 H6A 109.5 . .
N2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
Fe1 O4 H41 119(7) . .
Fe1 O4 H42 123(7) . .
H41 O4 H42 117(10) . .
H51 O5 H52 105(6) . .
H61 O6 H61 85(5) 4 .
Cl1 Fe2 Cl2 109.79(5) . 3_665
Cl1 Fe2 Cl2 109.79(5) . 2_655
Cl2 Fe2 Cl2 109.15(5) 3_665 2_655
Cl1 Fe2 Cl2 109.79(5) . .
Cl2 Fe2 Cl2 109.15(5) 3_665 .
Cl2 Fe2 Cl2 109.15(5) 2_655 .
Cl4 Fe3 Cl4 117.71(11) . 2
Cl4 Fe3 Cl4 117.71(11) . 3
Cl4 Fe3 Cl4 117.71(11) 2 3
Cl4 Fe3 Cl3 98.8(2) . .
Cl4 Fe3 Cl3 98.8(2) 2 .
Cl4 Fe3 Cl3 98.8(2) 3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 O1 1.9101(8) .
Fe1 O2 2.000(4) .
Fe1 O2 2.000(4) 4
Fe1 O3 2.029(3) 5
Fe1 O3 2.029(3) 2
Fe1 O4 2.048(5) .
O1 Fe1 1.9101(8) 2
O1 Fe1 1.9101(8) 3
O2 C1 1.253(6) .
O3 C1 1.241(6) .
O3 Fe1 2.029(3) 3
C1 C2 1.499(7) .
C2 N1 1.449(7) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
N1 C3 1.305(8) .
N1 C5 1.359(9) .
C3 N2 1.336(7) .
C3 H3A 0.9300 .
N2 C4 1.355(10) .
N2 C6 1.469(9) .
C4 C5 1.356(10) .
C4 H4A 0.9300 .
C5 H5A 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
O4 H41 0.90(4) .
O4 H42 0.90(4) .
O5 H51 0.94(4) .
O5 H52 0.95(4) .
O6 H61 1.06(4) 4
O6 H61 1.06(4) .
Fe2 Cl1 2.170(3) .
Fe2 Cl2 2.1874(16) 3_665
Fe2 Cl2 2.1874(15) 2_655
Fe2 Cl2 2.1874(16) .
Fe3 Cl4 2.169(4) .
Fe3 Cl4 2.169(4) 2
Fe3 Cl4 2.169(4) 3
Fe3 Cl3 2.327(5) .
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 H41 Cl11 0.90(4) 2.18(6) 3.067(6) 166(20) .
O4 H42 O5 0.90(4) 1.71(4) 2.596(9) 170(11) .
O5 H51 Cl11 0.94(4) 2.18(4) 3.111(9) 175(15) 3_565
O5 H52 Cl12 0.95(4) 2.21(5) 3.150(12) 170(15) .
O6 H61 Cl1 1.06(4) 2.85(6) 3.790(7) 148(7) .