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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/87/4128732.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_4128732
loop_
_publ_author_name
'Kepler, Slade'
'Zeller, Matthias'
'Rosokha, Sergiy V.'
_publ_section_title
;
 Anion-π Complexes of Halides with p-Benzoquinones: Structures,
 Thermodynamics, and Criteria of Charge Transfer to Electron Transfer
 Transition.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9338
_journal_page_last               9348
_journal_paper_doi               10.1021/jacs.9b03277
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         '2(C12 H28 N), C6 F4 O2, 2(C H2 Cl2), 2Br'
_chemical_formula_sum            'C32 H60 Br2 Cl4 F4 N2 O2'
_chemical_formula_weight         882.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                92.465(3)
_cell_angle_beta                 104.135(3)
_cell_angle_gamma                112.842(3)
_cell_formula_units_Z            1
_cell_length_a                   8.6884(8)
_cell_length_b                   9.4552(8)
_cell_length_c                   14.6981(12)
_cell_measurement_reflns_used    5236
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6019
_cell_measurement_theta_min      2.3672
_cell_volume                     1066.17(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12876
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         2.576
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  0.5633
_exptl_absorpt_correction_T_min  0.4064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0740P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2907
_reflns_number_total             4883
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b03277_si_006.cif
_cod_data_source_block           RS89_0m
_cod_database_code               4128732
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.668
_shelx_estimated_absorpt_t_max   0.898
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
C1 C 0.6418(5) 0.1313(5) 0.5640(3) 0.0420(10) Uani 1 1 d . .
C2 C 0.6703(5) 0.0160(5) 0.5066(3) 0.0396(9) Uani 1 1 d . .
C3 C 0.5413(5) -0.1015(5) 0.4478(3) 0.0422(10) Uani 1 1 d . .
C4 C 0.0451(5) 0.1451(4) 0.2567(3) 0.0359(9) Uani 1 1 d . .
H4A H 0.155238 0.144403 0.295525 0.043 Uiso 1 1 calc R U
H4B H 0.035232 0.116241 0.189347 0.043 Uiso 1 1 calc R U
C5 C -0.1053(5) 0.0215(5) 0.2824(3) 0.0438(10) Uani 1 1 d . .
H5A H -0.215987 0.027782 0.249743 0.053 Uiso 1 1 calc R U
H5B H -0.088257 0.038915 0.351757 0.053 Uiso 1 1 calc R U
C6 C -0.1141(6) -0.1388(5) 0.2525(3) 0.0518(11) Uani 1 1 d . .
H6A H -0.141306 -0.159274 0.183242 0.078 Uiso 1 1 calc R U
H6B H -0.205006 -0.218029 0.273567 0.078 Uiso 1 1 calc R U
H6C H -0.001490 -0.142075 0.281609 0.078 Uiso 1 1 calc R U
C7 C 0.0503(5) 0.3550(4) 0.3704(3) 0.0338(8) Uani 1 1 d . .
H7A H 0.060356 0.463123 0.376649 0.041 Uiso 1 1 calc R U
H7B H -0.065012 0.287296 0.377177 0.041 Uiso 1 1 calc R U
C8 C 0.1904(6) 0.3438(5) 0.4514(3) 0.0444(10) Uani 1 1 d . .
H8A H 0.175216 0.234314 0.450060 0.053 Uiso 1 1 calc R U
H8B H 0.306735 0.405861 0.443678 0.053 Uiso 1 1 calc R U
C9 C 0.1783(6) 0.4031(5) 0.5447(3) 0.0505(11) Uani 1 1 d . .
H9A H 0.192962 0.511322 0.545625 0.076 Uiso 1 1 calc R U
H9B H 0.269998 0.397033 0.596478 0.076 Uiso 1 1 calc R U
H9C H 0.064145 0.339627 0.552809 0.076 Uiso 1 1 calc R U
C10 C -0.0973(5) 0.3165(4) 0.1983(3) 0.0349(9) Uani 1 1 d . .
H10A H -0.098428 0.277780 0.134339 0.042 Uiso 1 1 calc R U
H10B H -0.205411 0.244492 0.210966 0.042 Uiso 1 1 calc R U
C11 C -0.1017(5) 0.4751(5) 0.1964(3) 0.0414(10) Uani 1 1 d . .
H11A H 0.016128 0.555237 0.202111 0.050 Uiso 1 1 calc R U
H11B H -0.140586 0.501033 0.250282 0.050 Uiso 1 1 calc R U
C12 C -0.2274(6) 0.4712(5) 0.1029(3) 0.0490(11) Uani 1 1 d . .
H12A H -0.182782 0.454280 0.050241 0.073 Uiso 1 1 calc R U
H12B H -0.239015 0.570199 0.102680 0.073 Uiso 1 1 calc R U
H12C H -0.341568 0.386450 0.095695 0.073 Uiso 1 1 calc R U
C13 C 0.2279(5) 0.4199(5) 0.2575(3) 0.0383(9) Uani 1 1 d . .
H13A H 0.322107 0.396772 0.297729 0.046 Uiso 1 1 calc R U
H13B H 0.248177 0.526793 0.281812 0.046 Uiso 1 1 calc R U
C14 C 0.2445(5) 0.4171(5) 0.1572(3) 0.0464(10) Uani 1 1 d . .
H14A H 0.232278 0.313094 0.132464 0.056 Uiso 1 1 calc R U
H14B H 0.151297 0.439360 0.115156 0.056 Uiso 1 1 calc R U
C15 C 0.4214(6) 0.5388(6) 0.1582(4) 0.0609(13) Uani 1 1 d . .
H15A H 0.437394 0.531534 0.094714 0.091 Uiso 1 1 calc R U
H15B H 0.512716 0.521081 0.203821 0.091 Uiso 1 1 calc R U
H15C H 0.428286 0.642361 0.176765 0.091 Uiso 1 1 calc R U
C16 C 0.3270(7) -0.0437(7) 0.0820(4) 0.0781(17) Uani 1 1 d . .
H16A H 0.409594 -0.086766 0.071642 0.094 Uiso 1 1 calc R U
H16B H 0.376557 0.018705 0.146234 0.094 Uiso 1 1 calc R U
Br1 Br 0.52288(5) 0.19312(5) 0.31096(3) 0.04789(18) Uani 1 1 d . .
Cl1 Cl 0.1302(2) -0.1955(2) 0.07683(13) 0.1011(6) Uani 1 1 d . .
Cl2 Cl 0.3048(2) 0.07762(19) -0.00267(12) 0.0908(5) Uani 1 1 d . .
F1 F 0.8360(3) 0.0420(3) 0.51654(19) 0.0573(7) Uani 1 1 d . .
F2 F 0.5678(3) -0.2021(3) 0.39399(19) 0.0600(7) Uani 1 1 d . .
N1 N 0.0570(4) 0.3096(3) 0.2705(2) 0.0314(7) Uani 1 1 d . .
O1 O 0.7629(4) 0.2416(4) 0.6168(3) 0.0723(11) Uani 1 1 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'
Br Br -0.2901 2.4595 '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'
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'
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 C1 C3 123.3(4) . 2_656
O1 C1 C2 121.6(4) . .
C3 C1 C2 115.1(3) 2_656 .
C3 C2 F1 122.1(4) . .
C3 C2 C1 122.3(4) . .
F1 C2 C1 115.6(3) . .
C2 C3 F2 122.0(4) . .
C2 C3 C1 122.6(4) . 2_656
F2 C3 C1 115.4(4) . 2_656
N1 C4 C5 115.7(3) . .
N1 C4 H4A 108.4 . .
C5 C4 H4A 108.4 . .
N1 C4 H4B 108.4 . .
C5 C4 H4B 108.4 . .
H4A C4 H4B 107.4 . .
C4 C5 C6 109.4(3) . .
C4 C5 H5A 109.8 . .
C6 C5 H5A 109.8 . .
C4 C5 H5B 109.8 . .
C6 C5 H5B 109.8 . .
H5A C5 H5B 108.2 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 N1 115.2(3) . .
C8 C7 H7A 108.5 . .
N1 C7 H7A 108.5 . .
C8 C7 H7B 108.5 . .
N1 C7 H7B 108.5 . .
H7A C7 H7B 107.5 . .
C9 C8 C7 109.9(3) . .
C9 C8 H8A 109.7 . .
C7 C8 H8A 109.7 . .
C9 C8 H8B 109.7 . .
C7 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 N1 116.0(3) . .
C11 C10 H10A 108.3 . .
N1 C10 H10A 108.3 . .
C11 C10 H10B 108.3 . .
N1 C10 H10B 108.3 . .
H10A C10 H10B 107.4 . .
C10 C11 C12 108.4(3) . .
C10 C11 H11A 110.0 . .
C12 C11 H11A 110.0 . .
C10 C11 H11B 110.0 . .
C12 C11 H11B 110.0 . .
H11A C11 H11B 108.4 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N1 C13 C14 116.8(3) . .
N1 C13 H13A 108.1 . .
C14 C13 H13A 108.1 . .
N1 C13 H13B 108.1 . .
C14 C13 H13B 108.1 . .
H13A C13 H13B 107.3 . .
C15 C14 C13 108.9(4) . .
C15 C14 H14A 109.9 . .
C13 C14 H14A 109.9 . .
C15 C14 H14B 109.9 . .
C13 C14 H14B 109.9 . .
H14A C14 H14B 108.3 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
Cl1 C16 Cl2 112.5(3) . .
Cl1 C16 H16A 109.1 . .
Cl2 C16 H16A 109.1 . .
Cl1 C16 H16B 109.1 . .
Cl2 C16 H16B 109.1 . .
H16A C16 H16B 107.8 . .
C13 N1 C4 108.7(3) . .
C13 N1 C10 111.6(3) . .
C4 N1 C10 108.1(3) . .
C13 N1 C7 108.6(3) . .
C4 N1 C7 111.2(3) . .
C10 N1 C7 108.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.215(5) .
C1 C3 1.467(6) 2_656
C1 C2 1.481(6) .
C2 C3 1.309(6) .
C2 F1 1.332(4) .
C3 F2 1.334(4) .
C4 N1 1.519(5) .
C4 C5 1.520(5) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.528(6) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.520(5) .
C7 N1 1.533(5) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.502(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.516(5) .
C10 N1 1.519(5) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.521(6) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 N1 1.511(5) .
C13 C14 1.517(6) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.516(6) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 Cl1 1.735(6) .
C16 Cl2 1.755(6) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
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
O1 C1 C2 C3 -178.4(5) . .
C3 C1 C2 C3 1.8(7) 2_656 .
O1 C1 C2 F1 -0.4(6) . .
C3 C1 C2 F1 179.9(4) 2_656 .
F1 C2 C3 F2 -0.2(7) . .
C1 C2 C3 F2 177.7(4) . .
F1 C2 C3 C1 -179.9(4) . 2_656
C1 C2 C3 C1 -2.0(8) . 2_656
N1 C4 C5 C6 172.5(3) . .
N1 C7 C8 C9 175.5(3) . .
N1 C10 C11 C12 162.4(3) . .
N1 C13 C14 C15 178.1(4) . .
C14 C13 N1 C4 71.7(4) . .
C14 C13 N1 C10 -47.5(4) . .
C14 C13 N1 C7 -167.3(3) . .
C5 C4 N1 C13 170.7(3) . .
C5 C4 N1 C10 -68.0(4) . .
C5 C4 N1 C7 51.3(4) . .
C11 C10 N1 C13 -56.5(4) . .
C11 C10 N1 C4 -176.0(3) . .
C11 C10 N1 C7 63.2(4) . .
C8 C7 N1 C13 -62.1(4) . .
C8 C7 N1 C4 57.3(4) . .
C8 C7 N1 C10 176.3(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168334013
