#------------------------------------------------------------------------------
#$Date: 2019-11-02 08:15:42 +0200 (Sat, 02 Nov 2019) $
#$Revision: 221066 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/79/4127908.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_4127908
loop_
_publ_author_name
'Horibe, Takahiro'
'Ohmura, Shuhei'
'Ishihara, Kazuaki'
_publ_section_title
;
 Structure and Reactivity of Aromatic Radical Cations Generated by
 FeCl₃.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1877
_journal_page_last               1881
_journal_paper_doi               10.1021/jacs.8b12827
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C18 H22 Cl4 Fe O2'
_chemical_formula_sum            'C18 H22 Cl4 Fe O2'
_chemical_formula_weight         468.03
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                78.7715(10)
_cell_angle_beta                 84.154(11)
_cell_angle_gamma                77.5726(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5142(12)
_cell_length_b                   8.8368(13)
_cell_length_c                   14.135(2)
_cell_measurement_reflns_used    3711
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     1016.7(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8514
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         3.029
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.275
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0213
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0320P)²+0.3445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3937
_reflns_number_total             4323
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja8b12827_si_001.cif
_cod_data_source_block           20161109-1
_cod_database_code               4127908
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
FE1 Fe 0.72555(2) 0.27670(2) 0.23838(2) 0.01970(6) Uani 1 1 d . .
CL1 Cl 0.71303(5) 0.31408(4) 0.38872(2) 0.03035(9) Uani 1 1 d . .
CL2 Cl 0.97943(4) 0.24550(5) 0.18580(3) 0.03147(9) Uani 1 1 d . .
CL3 Cl 0.57979(5) 0.48158(4) 0.15113(3) 0.03362(9) Uani 1 1 d . .
CL4 Cl 0.63281(5) 0.06889(4) 0.22503(3) 0.03528(10) Uani 1 1 d . .
O1 O 0.61428(11) 0.14173(11) 0.62706(7) 0.02172(19) Uani 1 1 d . .
O2 O 0.71363(11) 0.95450(11) 0.94937(7) 0.0226(2) Uani 1 1 d . .
C1 C 0.54727(15) 0.07982(14) 0.56716(9) 0.0166(2) Uani 1 1 d . .
C2 C 0.39037(16) 0.12797(14) 0.53366(9) 0.0178(2) Uani 1 1 d . .
C3 C 0.85467(16) 0.96421(15) 0.97711(9) 0.0179(2) Uani 1 1 d . .
C4 C 0.24529(17) 0.25926(15) 0.54766(10) 0.0229(3) Uani 1 1 d . .
H4 H 0.237894 0.301744 0.608921 0.027 Uiso 1 1 calc R U
C5 C 0.65168(15) -0.05055(14) 0.53303(9) 0.0180(2) Uani 1 1 d . .
C6 C 0.81049(17) 1.25091(15) 0.87384(10) 0.0211(3) Uani 1 1 d . .
H6 H 0.693201 1.254929 0.869200 0.025 Uiso 1 1 calc R U
C7 C 0.89812(16) 1.11343(14) 0.94236(9) 0.0176(2) Uani 1 1 d . .
C8 C 1.03690(16) 1.15241(14) 0.96449(9) 0.0176(2) Uani 1 1 d . .
C9 C 1.06992(18) 1.30505(16) 0.80171(10) 0.0250(3) Uani 1 1 d . .
H9A H 1.084287 1.406703 0.761411 0.030 Uiso 1 1 calc R U
H9B H 1.167313 1.223740 0.792264 0.030 Uiso 1 1 calc R U
C10 C 0.91655(18) 1.25630(17) 0.77691(10) 0.0264(3) Uani 1 1 d . .
H10A H 0.943272 1.151906 0.756966 0.032 Uiso 1 1 calc R U
H10B H 0.861266 1.334814 0.724609 0.032 Uiso 1 1 calc R U
C11 C 0.81898(17) -0.13055(16) 0.56247(10) 0.0237(3) Uani 1 1 d . .
H11 H 0.878940 -0.067608 0.591988 0.028 Uiso 1 1 calc R U
C12 C 1.03599(17) 1.31977(15) 0.91005(9) 0.0209(3) Uani 1 1 d . .
H12 H 1.103634 1.380553 0.935485 0.025 Uiso 1 1 calc R U
C13 C 0.85299(17) 1.38706(15) 0.91271(10) 0.0238(3) Uani 1 1 d . .
H13A H 0.805407 1.394884 0.978899 0.029 Uiso 1 1 calc R U
H13B H 0.824485 1.489746 0.869107 0.029 Uiso 1 1 calc R U
C14 C 0.80070(19) -0.29410(17) 0.62275(11) 0.0289(3) Uani 1 1 d . .
H14A H 0.902598 -0.350368 0.652175 0.035 Uiso 1 1 calc R U
H14B H 0.713769 -0.282616 0.674533 0.035 Uiso 1 1 calc R U
C15 C 0.89241(17) -0.17819(18) 0.46532(11) 0.0273(3) Uani 1 1 d . .
H15A H 0.901072 -0.086329 0.413749 0.033 Uiso 1 1 calc R U
H15B H 0.997859 -0.251913 0.471490 0.033 Uiso 1 1 calc R U
C16 C 0.52756(18) 0.27929(17) 0.66380(11) 0.0290(3) Uani 1 1 d . .
H16A H 0.487186 0.361778 0.609833 0.035 Uiso 1 1 calc R U
H16B H 0.599816 0.317463 0.699199 0.035 Uiso 1 1 calc R U
H16C H 0.436669 0.252240 0.707360 0.035 Uiso 1 1 calc R U
C17 C 0.24237(19) 0.38202(16) 0.45263(11) 0.0288(3) Uani 1 1 d . .
H17A H 0.159883 0.478196 0.458292 0.035 Uiso 1 1 calc R U
H17B H 0.348836 0.411401 0.435389 0.035 Uiso 1 1 calc R U
C18 C 0.64870(18) 0.81323(17) 0.98072(12) 0.0305(3) Uani 1 1 d . .
H18A H 0.717961 0.726173 0.953568 0.037 Uiso 1 1 calc R U
H18B H 0.539874 0.831025 0.958383 0.037 Uiso 1 1 calc R U
H18C H 0.644263 0.786766 1.051434 0.037 Uiso 1 1 calc R U
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Fe Fe 0.3463 0.8444
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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
CL2 FE1 CL3 111.010(18) . .
CL2 FE1 CL4 109.101(18) . .
CL3 FE1 CL4 107.29(2) . .
CL2 FE1 CL1 107.207(19) . .
CL3 FE1 CL1 109.411(19) . .
CL4 FE1 CL1 112.858(17) . .
C1 O1 C16 120.49(10) . .
C3 O2 C18 120.95(10) . .
O1 C1 C2 128.24(12) . .
O1 C1 C5 113.73(11) . .
C2 C1 C5 118.03(11) . .
C5 C2 C1 118.37(11) 2_656 .
C5 C2 C4 105.76(11) 2_656 .
C1 C2 C4 135.74(11) . .
O2 C3 C8 128.42(12) . 2_777
O2 C3 C7 113.68(11) . .
C8 C3 C7 117.91(12) 2_777 .
C2 C4 C15 100.00(10) . 2_656
C2 C4 C17 105.55(11) . .
C15 C4 C17 101.13(11) 2_656 .
C2 C4 H4 116.0 . .
C15 C4 H4 116.0 2_656 .
C17 C4 H4 116.0 . .
C2 C5 C1 123.55(12) 2_656 .
C2 C5 C11 108.21(11) 2_656 .
C1 C5 C11 128.22(11) . .
C7 C6 C13 99.60(10) . .
C7 C6 C10 105.33(11) . .
C13 C6 C10 100.73(11) . .
C7 C6 H6 116.3 . .
C13 C6 H6 116.3 . .
C10 C6 H6 116.3 . .
C8 C7 C3 123.96(11) . .
C8 C7 C6 108.03(11) . .
C3 C7 C6 127.95(12) . .
C7 C8 C3 118.10(11) . 2_777
C7 C8 C12 105.99(11) . .
C3 C8 C12 135.77(12) 2_777 .
C10 C9 C12 103.33(11) . .
C10 C9 H9A 111.1 . .
C12 C9 H9A 111.1 . .
C10 C9 H9B 111.1 . .
C12 C9 H9B 111.1 . .
H9A C9 H9B 109.1 . .
C9 C10 C6 103.25(11) . .
C9 C10 H10A 111.1 . .
C6 C10 H10A 111.1 . .
C9 C10 H10B 111.1 . .
C6 C10 H10B 111.1 . .
H10A C10 H10B 109.1 . .
C5 C11 C15 99.25(11) . .
C5 C11 C14 105.24(11) . .
C15 C11 C14 100.68(11) . .
C5 C11 H11 116.4 . .
C15 C11 H11 116.4 . .
C14 C11 H11 116.4 . .
C8 C12 C13 100.01(11) . .
C8 C12 C9 105.46(10) . .
C13 C12 C9 100.54(11) . .
C8 C12 H12 116.2 . .
C13 C12 H12 116.2 . .
C9 C12 H12 116.2 . .
C6 C13 C12 94.79(10) . .
C6 C13 H13A 112.8 . .
C12 C13 H13A 112.8 . .
C6 C13 H13B 112.8 . .
C12 C13 H13B 112.8 . .
H13A C13 H13B 110.2 . .
C17 C14 C11 103.61(11) 2_656 .
C17 C14 H14A 111.0 2_656 .
C11 C14 H14A 111.0 . .
C17 C14 H14B 111.0 2_656 .
C11 C14 H14B 111.0 . .
H14A C14 H14B 109.0 . .
C4 C15 C11 94.55(11) 2_656 .
C4 C15 H15A 112.8 2_656 .
C11 C15 H15A 112.8 . .
C4 C15 H15B 112.8 2_656 .
C11 C15 H15B 112.8 . .
H15A C15 H15B 110.3 . .
O1 C16 H16A 109.5 . .
O1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
O1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C14 C17 C4 103.16(11) 2_656 .
C14 C17 H17A 111.1 2_656 .
C4 C17 H17A 111.1 . .
C14 C17 H17B 111.1 2_656 .
C4 C17 H17B 111.1 . .
H17A C17 H17B 109.1 . .
O2 C18 H18A 109.5 . .
O2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
FE1 CL2 2.1901(5) .
FE1 CL3 2.1941(4) .
FE1 CL4 2.1956(5) .
FE1 CL1 2.2019(5) .
O1 C1 1.3248(15) .
O1 C16 1.4401(16) .
O2 C3 1.3253(16) .
O2 C18 1.4464(16) .
C1 C2 1.4127(18) .
C1 C5 1.4277(17) .
C2 C5 1.3822(17) 2_656
C2 C4 1.5276(18) .
C3 C8 1.4178(17) 2_777
C3 C7 1.4274(17) .
C4 C15 1.542(2) 2_656
C4 C17 1.552(2) .
C4 H4 1.0000 .
C5 C2 1.3822(17) 2_656
C5 C11 1.5082(18) .
C6 C7 1.5065(17) .
C6 C13 1.5381(19) .
C6 C10 1.5608(19) .
C6 H6 1.0000 .
C7 C8 1.3802(18) .
C8 C3 1.4179(17) 2_777
C8 C12 1.5273(17) .
C9 C10 1.552(2) .
C9 C12 1.5546(19) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C15 1.546(2) .
C11 C14 1.559(2) .
C11 H11 1.0000 .
C12 C13 1.5429(19) .
C12 H12 1.0000 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C17 1.549(2) 2_656
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C4 1.542(2) 2_656
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C14 1.549(2) 2_656
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
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_1
_geom_torsion_site_symmetry_4
C16 O1 C1 C2 -2.53(19) . .
C16 O1 C1 C5 176.68(12) . .
O1 C1 C2 C5 176.72(12) . 2_656
C5 C1 C2 C5 -2.45(19) . 2_656
O1 C1 C2 C4 1.5(2) . .
C5 C1 C2 C4 -177.72(13) . .
C18 O2 C3 C8 1.8(2) . 2_777
C18 O2 C3 C7 -177.98(12) . .
C5 C2 C4 C15 33.41(13) 2_656 2_656
C1 C2 C4 C15 -150.91(15) . 2_656
C5 C2 C4 C17 -71.21(13) 2_656 .
C1 C2 C4 C17 104.46(16) . .
O1 C1 C5 C2 -176.70(12) . 2_656
C2 C1 C5 C2 2.6(2) . 2_656
O1 C1 C5 C11 5.05(19) . .
C2 C1 C5 C11 -175.66(12) . .
O2 C3 C7 C8 177.85(12) . .
C8 C3 C7 C8 -2.0(2) 2_777 .
O2 C3 C7 C6 -5.14(19) . .
C8 C3 C7 C6 175.04(12) 2_777 .
C13 C6 C7 C8 -34.31(13) . .
C10 C6 C7 C8 69.71(13) . .
C13 C6 C7 C3 148.31(13) . .
C10 C6 C7 C3 -107.68(14) . .
C3 C7 C8 C3 2.0(2) . 2_777
C6 C7 C8 C3 -175.55(11) . 2_777
C3 C7 C8 C12 178.47(12) . .
C6 C7 C8 C12 0.95(13) . .
C12 C9 C10 C6 0.79(13) . .
C7 C6 C10 C9 -68.24(13) . .
C13 C6 C10 C9 34.94(12) . .
C2 C5 C11 C15 34.22(13) 2_656 .
C1 C5 C11 C15 -147.31(13) . .
C2 C5 C11 C14 -69.60(14) 2_656 .
C1 C5 C11 C14 108.86(14) . .
C7 C8 C12 C13 32.68(13) . .
C3 C8 C12 C13 -151.75(14) 2_777 .
C7 C8 C12 C9 -71.30(13) . .
C3 C8 C12 C9 104.28(16) 2_777 .
C10 C9 C12 C8 67.47(13) . .
C10 C9 C12 C13 -36.11(12) . .
C7 C6 C13 C12 51.38(11) . .
C10 C6 C13 C12 -56.38(11) . .
C8 C12 C13 C6 -51.02(11) . .
C9 C12 C13 C6 56.93(11) . .
C5 C11 C14 C17 67.73(14) . 2_656
C15 C11 C14 C17 -35.03(14) . 2_656
C5 C11 C15 C4 -51.64(12) . 2_656
C14 C11 C15 C4 55.92(12) . 2_656
C2 C4 C17 C14 67.97(14) . 2_656
C15 C4 C17 C14 -35.83(14) 2_656 2_656
