#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/65/2226526.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226526
loop_
_publ_author_name
'Ge, Jia-Zhen'
'Zhao, Min-Min'
_publ_section_title
;
 4-Fluoroanilinium tetrachloridoferrate(III) 18-crown-6 clathrate
;
_journal_coeditor_code           IM2203
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m739
_journal_paper_doi               10.1107/S160053681002009X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '(C6 H7 F N) [Fe Cl4], C12 H24 O6'
_chemical_formula_moiety         'C6 H7 F N +, Cl4 Fe -, C12 H24 O6'
_chemical_formula_sum            'C18 H31 Cl4 F Fe N O6'
_chemical_formula_weight         574.09
_chemical_name_common
'4-Fluoroanilinium tetrachloridoferrate(III) 18-crown-6 clathrate'
_chemical_name_systematic
;
4-Fluoroanilinium
tetrachloridoferrate(III)--1,4,7,10,13,16-hexaoxacyclooctadecane (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.82(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.450(10)
_cell_length_b                   24.14(2)
_cell_length_c                   9.719(9)
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4603
_cell_measurement_theta_min      2.2718
_cell_volume                     2667(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0684
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26978
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_T_max  0.818
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.351
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         6039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0780
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1312P)²+0.8151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2345
_refine_ls_wR_factor_ref         0.2706
_reflns_number_gt                3173
_reflns_number_total             6039
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2203.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226526
_cod_database_fobs_code          2226526
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5434(4) 0.09467(19) 0.7021(5) 0.0842(13) Uani d . 1 . .
O O2 0.7834(4) 0.06611(18) 0.6808(4) 0.0816(12) Uani d . 1 . .
O O3 0.9463(3) 0.14900(18) 0.7297(5) 0.0741(11) Uani d . 1 . .
O O4 0.8972(4) 0.23864(18) 0.8904(5) 0.0849(13) Uani d . 1 . .
O O5 0.6635(4) 0.25943(19) 0.9254(5) 0.0903(14) Uani d . 1 . .
O O6 0.4892(4) 0.1787(2) 0.8722(5) 0.0895(14) Uani d . 1 . .
C C1 0.5820(8) 0.0397(3) 0.6788(9) 0.102(2) Uani d . 1 . .
H H1A 0.5188 0.0190 0.6268 0.122 Uiso calc R 1 . .
H H1B 0.6025 0.0212 0.7670 0.122 Uiso calc R 1 . .
C C2 0.6847(7) 0.0408(3) 0.6013(8) 0.093(2) Uani d . 1 . .
H H2A 0.7049 0.0033 0.5776 0.112 Uiso calc R 1 . .
H H2B 0.6653 0.0613 0.5158 0.112 Uiso calc R 1 . .
C C3 0.8831(6) 0.0647(3) 0.6178(7) 0.0800(18) Uani d . 1 . .
H H3A 0.8688 0.0824 0.5278 0.096 Uiso calc R 1 . .
H H3B 0.9053 0.0265 0.6039 0.096 Uiso calc R 1 . .
C C4 0.9802(6) 0.0937(3) 0.7041(7) 0.0798(18) Uani d . 1 . .
H H4A 0.9987 0.0743 0.7913 0.096 Uiso calc R 1 . .
H H4B 1.0500 0.0939 0.6565 0.096 Uiso calc R 1 . .
C C5 1.0380(5) 0.1806(3) 0.7950(8) 0.086(2) Uani d . 1 . .
H H5A 1.1034 0.1806 0.7400 0.104 Uiso calc R 1 . .
H H5B 1.0650 0.1648 0.8850 0.104 Uiso calc R 1 . .
C C6 0.9964(6) 0.2383(3) 0.8120(9) 0.091(2) Uani d . 1 . .
H H6A 1.0596 0.2603 0.8595 0.109 Uiso calc R 1 . .
H H6B 0.9739 0.2546 0.7216 0.109 Uiso calc R 1 . .
C C7 0.8554(8) 0.2921(3) 0.9050(10) 0.104(3) Uani d . 1 . .
H H7A 0.8286 0.3074 0.8145 0.124 Uiso calc R 1 . .
H H7B 0.9180 0.3154 0.9488 0.124 Uiso calc R 1 . .
C C8 0.7560(8) 0.2905(3) 0.9917(11) 0.113(3) Uani d . 1 . .
H H8A 0.7825 0.2743 1.0812 0.136 Uiso calc R 1 . .
H H8B 0.7293 0.3280 1.0067 0.136 Uiso calc R 1 . .
C C9 0.5658(7) 0.2584(4) 0.9976(9) 0.100(2) Uani d . 1 . .
H H9A 0.5470 0.2955 1.0261 0.120 Uiso calc R 1 . .
H H9B 0.5813 0.2355 1.0798 0.120 Uiso calc R 1 . .
C C10 0.4667(6) 0.2353(3) 0.9035(9) 0.091(2) Uani d . 1 . .
H H10A 0.3948 0.2377 0.9469 0.109 Uiso calc R 1 . .
H H10B 0.4561 0.2567 0.8184 0.109 Uiso calc R 1 . .
C C11 0.4035(6) 0.1551(4) 0.7758(10) 0.101(2) Uani d . 1 . .
H H11A 0.3981 0.1759 0.6899 0.122 Uiso calc R 1 . .
H H11B 0.3276 0.1569 0.8108 0.122 Uiso calc R 1 . .
C C12 0.4324(6) 0.0968(3) 0.7491(10) 0.100(2) Uani d . 1 . .
H H12A 0.4329 0.0753 0.8334 0.119 Uiso calc R 1 . .
H H12B 0.3736 0.0813 0.6797 0.119 Uiso calc R 1 . .
F F1 0.8204(4) 0.00256(15) 0.3199(4) 0.0906(12) Uani d . 1 . .
N N1 0.7364(3) 0.14716(16) -0.1213(4) 0.0498(9) Uani d . 1 . .
H H1C 0.7853 0.1760 -0.1140 0.075 Uiso calc R 1 . .
H H1D 0.6625 0.1592 -0.1276 0.075 Uiso calc R 1 . .
H H1E 0.7467 0.1277 -0.1967 0.075 Uiso calc R 1 . .
C C13 0.8711(5) 0.0971(3) 0.0489(7) 0.0748(17) Uani d . 1 . .
H H13A 0.9340 0.1117 0.0085 0.090 Uiso calc R 1 . .
C C14 0.7606(4) 0.11179(19) 0.0016(5) 0.0493(11) Uani d . 1 . .
C C15 0.6684(5) 0.0924(3) 0.0657(7) 0.0699(16) Uani d . 1 . .
H H15A 0.5920 0.1037 0.0355 0.084 Uiso calc R 1 . .
C C16 0.6894(6) 0.0558(3) 0.1752(7) 0.0758(17) Uani d . 1 . .
H H16A 0.6279 0.0427 0.2206 0.091 Uiso calc R 1 . .
C C17 0.8011(6) 0.0396(2) 0.2148(6) 0.0658(15) Uani d . 1 . .
C C18 0.8913(6) 0.0598(3) 0.1588(7) 0.0804(18) Uani d . 1 . .
H H18A 0.9676 0.0493 0.1922 0.096 Uiso calc R 1 . .
Fe Fe2 0.25883(7) 0.12580(3) 0.22601(9) 0.0635(3) Uani d . 1 . .
Cl Cl1 0.44359(16) 0.11643(9) 0.3030(3) 0.1179(8) Uani d . 1 . .
Cl Cl2 0.2109(2) 0.06493(9) 0.0642(2) 0.1121(7) Uani d . 1 . .
Cl Cl3 0.22522(16) 0.20828(7) 0.13775(19) 0.0840(5) Uani d . 1 . .
Cl Cl4 0.1561(2) 0.11388(10) 0.3981(2) 0.1144(8) Uani d . 1 . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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'
H H 0.0000 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O1 C1 . . 113.4(6) ?
C3 O2 C2 . . 113.5(5) ?
C5 O3 C4 . . 112.9(5) ?
C7 O4 C6 . . 111.2(5) ?
C9 O5 C8 . . 113.0(7) ?
C11 O6 C10 . . 113.7(6) ?
O1 C1 C2 . . 110.2(6) ?
O1 C1 H1A . . 109.6 ?
C2 C1 H1A . . 109.6 ?
O1 C1 H1B . . 109.6 ?
C2 C1 H1B . . 109.6 ?
H1A C1 H1B . . 108.1 ?
O2 C2 C1 . . 111.2(6) ?
O2 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
O2 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
O2 C3 C4 . . 110.3(6) ?
O2 C3 H3A . . 109.6 ?
C4 C3 H3A . . 109.6 ?
O2 C3 H3B . . 109.6 ?
C4 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
O3 C4 C3 . . 109.9(5) ?
O3 C4 H4A . . 109.7 ?
C3 C4 H4A . . 109.7 ?
O3 C4 H4B . . 109.7 ?
C3 C4 H4B . . 109.7 ?
H4A C4 H4B . . 108.2 ?
O3 C5 C6 . . 109.3(5) ?
O3 C5 H5A . . 109.8 ?
C6 C5 H5A . . 109.8 ?
O3 C5 H5B . . 109.8 ?
C6 C5 H5B . . 109.8 ?
H5A C5 H5B . . 108.3 ?
O4 C6 C5 . . 110.3(5) ?
O4 C6 H6A . . 109.6 ?
C5 C6 H6A . . 109.6 ?
O4 C6 H6B . . 109.6 ?
C5 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
O4 C7 C8 . . 109.2(7) ?
O4 C7 H7A . . 109.8 ?
C8 C7 H7A . . 109.8 ?
O4 C7 H7B . . 109.8 ?
C8 C7 H7B . . 109.8 ?
H7A C7 H7B . . 108.3 ?
O5 C8 C7 . . 109.9(7) ?
O5 C8 H8A . . 109.7 ?
C7 C8 H8A . . 109.7 ?
O5 C8 H8B . . 109.7 ?
C7 C8 H8B . . 109.7 ?
H8A C8 H8B . . 108.2 ?
O5 C9 C10 . . 107.4(7) ?
O5 C9 H9A . . 110.2 ?
C10 C9 H9A . . 110.2 ?
O5 C9 H9B . . 110.2 ?
C10 C9 H9B . . 110.2 ?
H9A C9 H9B . . 108.5 ?
O6 C10 C9 . . 110.3(6) ?
O6 C10 H10A . . 109.6 ?
C9 C10 H10A . . 109.6 ?
O6 C10 H10B . . 109.6 ?
C9 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.1 ?
O6 C11 C12 . . 110.7(6) ?
O6 C11 H11A . . 109.5 ?
C12 C11 H11A . . 109.5 ?
O6 C11 H11B . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
O1 C12 C11 . . 108.9(6) ?
O1 C12 H12A . . 109.9 ?
C11 C12 H12A . . 109.9 ?
O1 C12 H12B . . 109.9 ?
C11 C12 H12B . . 109.9 ?
H12A C12 H12B . . 108.3 ?
C14 N1 H1C . . 109.5 ?
C14 N1 H1D . . 109.5 ?
H1C N1 H1D . . 109.5 ?
C14 N1 H1E . . 109.5 ?
H1C N1 H1E . . 109.5 ?
H1D N1 H1E . . 109.5 ?
C14 C13 C18 . . 119.8(5) ?
C14 C13 H13A . . 120.1 ?
C18 C13 H13A . . 120.1 ?
C13 C14 C15 . . 120.0(5) ?
C13 C14 N1 . . 120.8(5) ?
C15 C14 N1 . . 119.2(5) ?
C14 C15 C16 . . 119.7(5) ?
C14 C15 H15A . . 120.1 ?
C16 C15 H15A . . 120.1 ?
C17 C16 C15 . . 118.5(5) ?
C17 C16 H16A . . 120.7 ?
C15 C16 H16A . . 120.7 ?
C18 C17 C16 . . 122.6(6) ?
C18 C17 F1 . . 119.3(6) ?
C16 C17 F1 . . 118.1(6) ?
C17 C18 C13 . . 119.2(6) ?
C17 C18 H18A . . 120.4 ?
C13 C18 H18A . . 120.4 ?
Cl1 Fe2 Cl2 . . 109.35(9) ?
Cl1 Fe2 Cl4 . . 108.36(13) ?
Cl2 Fe2 Cl4 . . 110.70(12) ?
Cl1 Fe2 Cl3 . . 110.46(9) ?
Cl2 Fe2 Cl3 . . 108.32(11) ?
Cl4 Fe2 Cl3 . . 109.66(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . 1.401(8) ?
O1 C1 . 1.425(9) ?
O2 C3 . 1.357(8) ?
O2 C2 . 1.428(8) ?
O3 C5 . 1.388(7) ?
O3 C4 . 1.420(7) ?
O4 C7 . 1.388(8) ?
O4 C6 . 1.441(8) ?
O5 C9 . 1.390(8) ?
O5 C8 . 1.391(9) ?
O6 C11 . 1.396(9) ?
O6 C10 . 1.428(8) ?
C1 C2 . 1.471(11) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.486(10) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.487(10) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.495(12) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.480(12) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.476(11) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
F1 C17 . 1.356(6) ?
N1 C14 . 1.467(6) ?
N1 H1C . 0.8900 ?
N1 H1D . 0.8900 ?
N1 H1E . 0.8900 ?
C13 C14 . 1.341(8) ?
C13 C18 . 1.396(8) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.371(7) ?
C15 C16 . 1.381(8) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.349(9) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.317(8) ?
C18 H18A . 0.9300 ?
Fe2 Cl1 . 2.170(3) ?
Fe2 Cl2 . 2.175(2) ?
Fe2 Cl4 . 2.175(3) ?
Fe2 Cl3 . 2.184(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1C O4 1_554 0.89 1.98 2.868(6) 176.3
N1 H1D O6 1_554 0.89 2.04 2.924(6) 173.0
N1 H1E O2 1_554 0.89 1.98 2.840(6) 161.6
