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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/4/12/87/4128733.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_4128733
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         'C12 H28 N, C6 F4 O2, I'
_chemical_formula_sum            'C18 H28 F4 I N O2'
_chemical_formula_weight         493.31
_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-2018/1
_cell_angle_alpha                105.366(5)
_cell_angle_beta                 97.509(6)
_cell_angle_gamma                110.255(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4008(14)
_cell_length_b                   10.9112(16)
_cell_length_c                   11.8382(18)
_cell_measurement_reflns_used    8855
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.1526
_cell_measurement_theta_min      3.1548
_cell_volume                     1064.8(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_refinement
;  
SHELXL-2018/1 (Sheldrick, 2015, 2018), 
SHELXLE Rev882 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.722
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.722
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18865
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.722
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.979
_diffrn_reflns_theta_min         3.155
_diffrn_source                   'sealed tube X-ray source'
_exptl_absorpt_coefficient_mu    1.549
_exptl_absorpt_correction_T_max  0.2692
_exptl_absorpt_correction_T_min  0.2177
_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            blue
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+0.4521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4598
_reflns_number_total             5800
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b03277_si_004.cif
_cod_data_source_block           RS53_0m
_cod_database_code               4128733
_shelx_shelxl_version_number     2018/1
_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   0.717
_shelx_estimated_absorpt_t_max   0.955
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
C7 C 0.0275(3) 0.8856(3) 0.2474(2) 0.0262(5) Uani 1 1 d . .
H7A H 0.090365 0.986125 0.287726 0.031 Uiso 1 1 calc R U
H7AB H -0.063663 0.859898 0.282908 0.031 Uiso 1 1 calc R U
C6 C 0.5333(4) 0.3998(3) 0.0402(3) 0.0336(6) Uani 1 1 d . .
C13 C 0.2596(3) 0.8312(3) 0.2110(2) 0.0257(5) Uani 1 1 d . .
H13A H 0.321738 0.779978 0.232530 0.031 Uiso 1 1 calc R U
H13B H 0.213940 0.790406 0.122631 0.031 Uiso 1 1 calc R U
C12 C 0.1541(4) 0.8432(3) 0.6100(3) 0.0411(7) Uani 1 1 d . .
H12A H 0.196563 0.771968 0.603277 0.062 Uiso 1 1 calc R U
H12B H 0.077257 0.830175 0.659004 0.062 Uiso 1 1 calc R U
H12C H 0.239178 0.935113 0.648544 0.062 Uiso 1 1 calc R U
C11 C 0.0757(3) 0.8314(3) 0.4851(3) 0.0332(6) Uani 1 1 d . .
H11A H 0.027211 0.899598 0.492055 0.040 Uiso 1 1 calc R U
H11B H -0.008051 0.737564 0.445018 0.040 Uiso 1 1 calc R U
C10 C 0.1951(3) 0.8580(3) 0.4091(2) 0.0275(5) Uani 1 1 d . .
H10A H 0.258614 0.958940 0.435793 0.033 Uiso 1 1 calc R U
H10B H 0.266479 0.812578 0.425290 0.033 Uiso 1 1 calc R U
C9 C -0.1359(4) 0.9364(3) 0.0964(3) 0.0386(7) Uani 1 1 d . .
H9A H -0.176257 0.915523 0.009898 0.058 Uiso 1 1 calc R U
H9B H -0.074805 1.036276 0.134810 0.058 Uiso 1 1 calc R U
H9C H -0.223545 0.907070 0.133521 0.058 Uiso 1 1 calc R U
C8 C -0.0314(3) 0.8586(3) 0.1138(3) 0.0329(6) Uani 1 1 d . .
H8A H -0.091390 0.758015 0.071599 0.040 Uiso 1 1 calc R U
H8AB H 0.058658 0.889718 0.078073 0.040 Uiso 1 1 calc R U
C14 C 0.3696(3) 0.9805(3) 0.2396(3) 0.0323(6) Uani 1 1 d . .
H14A H 0.438135 1.016119 0.322066 0.039 Uiso 1 1 calc R U
H14B H 0.308905 1.038231 0.236240 0.039 Uiso 1 1 calc R U
C15 C 0.4685(3) 0.9880(3) 0.1473(3) 0.0360(7) Uani 1 1 d . .
H15A H 0.400490 0.958535 0.066542 0.054 Uiso 1 1 calc R U
H15B H 0.523960 0.926889 0.148151 0.054 Uiso 1 1 calc R U
H15C H 0.544540 1.083521 0.167786 0.054 Uiso 1 1 calc R U
C16 C 0.0241(3) 0.6521(3) 0.2272(2) 0.0268(5) Uani 1 1 d . .
H16A H -0.077668 0.638280 0.248022 0.032 Uiso 1 1 calc R U
H16B H 0.003282 0.619430 0.137907 0.032 Uiso 1 1 calc R U
C18 C -0.0156(4) 0.4101(3) 0.2074(3) 0.0411(7) Uani 1 1 d . .
H18A H -0.023291 0.389506 0.120481 0.062 Uiso 1 1 calc R U
H18B H -0.119970 0.391821 0.222154 0.062 Uiso 1 1 calc R U
H18C H 0.027947 0.351329 0.236498 0.062 Uiso 1 1 calc R U
C17 C 0.0908(3) 0.5620(3) 0.2742(3) 0.0315(6) Uani 1 1 d . .
H17A H 0.098323 0.583670 0.361961 0.038 Uiso 1 1 calc R U
H17B H 0.197134 0.580605 0.261259 0.038 Uiso 1 1 calc R U
F1 F 0.2034(2) 0.47070(19) 0.51412(19) 0.0475(5) Uani 1 1 d . .
O1 O 0.2558(2) 0.2748(2) 0.3480(2) 0.0410(5) Uani 1 1 d . .
C1 C 0.3694(3) 0.3772(3) 0.4200(3) 0.0337(6) Uani 1 1 d . .
I1 I 0.60644(2) 0.73293(2) 0.32303(2) 0.03082(6) Uani 1 1 d . .
N1 N 0.1261(2) 0.8074(2) 0.27427(19) 0.0224(4) Uani 1 1 d . .
C2 C 0.3468(3) 0.4871(3) 0.5098(3) 0.0327(6) Uani 1 1 d . .
O2 O 0.2420(2) 0.5375(2) 0.03490(19) 0.0402(5) Uani 1 1 d . .
F2 F 0.4491(2) 0.7000(2) 0.6648(2) 0.0604(6) Uani 1 1 d . .
C3 C 0.4715(4) 0.6019(3) 0.5834(3) 0.0368(7) Uani 1 1 d . .
F3 F 0.3239(2) 0.36512(18) 0.13116(17) 0.0450(4) Uani 1 1 d . .
C5 C 0.4122(3) 0.4275(3) 0.0676(3) 0.0330(6) Uani 1 1 d . .
C4 C 0.3637(3) 0.5254(3) 0.0244(2) 0.0323(6) Uani 1 1 d . .
F4 F 0.5757(2) 0.30999(19) 0.07789(19) 0.0499(5) 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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
N1 C7 C8 114.4(2) . .
N1 C7 H7A 108.7 . .
C8 C7 H7A 108.7 . .
N1 C7 H7AB 108.7 . .
C8 C7 H7AB 108.7 . .
H7A C7 H7AB 107.6 . .
F4 C6 C5 121.8(3) . .
F4 C6 C4 115.7(2) . 2_665
C5 C6 C4 122.3(3) . 2_665
C14 C13 N1 116.00(19) . .
C14 C13 H13A 108.3 . .
N1 C13 H13A 108.3 . .
C14 C13 H13B 108.3 . .
N1 C13 H13B 108.3 . .
H13A C13 H13B 107.4 . .
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 . .
C12 C11 C10 110.3(2) . .
C12 C11 H11A 109.6 . .
C10 C11 H11A 109.6 . .
C12 C11 H11B 109.6 . .
C10 C11 H11B 109.6 . .
H11A C11 H11B 108.1 . .
N1 C10 C11 115.0(2) . .
N1 C10 H10A 108.5 . .
C11 C10 H10A 108.5 . .
N1 C10 H10B 108.5 . .
C11 C10 H10B 108.5 . .
H10A C10 H10B 107.5 . .
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 . .
C7 C8 C9 110.2(2) . .
C7 C8 H8A 109.6 . .
C9 C8 H8A 109.6 . .
C7 C8 H8AB 109.6 . .
C9 C8 H8AB 109.6 . .
H8A C8 H8AB 108.1 . .
C13 C14 C15 108.8(2) . .
C13 C14 H14A 109.9 . .
C15 C14 H14A 109.9 . .
C13 C14 H14B 109.9 . .
C15 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 . .
C17 C16 N1 116.0(2) . .
C17 C16 H16A 108.3 . .
N1 C16 H16A 108.3 . .
C17 C16 H16B 108.3 . .
N1 C16 H16B 108.3 . .
H16A C16 H16B 107.4 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C16 C17 C18 109.2(2) . .
C16 C17 H17A 109.8 . .
C18 C17 H17A 109.8 . .
C16 C17 H17B 109.8 . .
C18 C17 H17B 109.8 . .
H17A C17 H17B 108.3 . .
O1 C1 C3 122.2(3) . 2_666
O1 C1 C2 121.1(3) . .
C3 C1 C2 116.6(3) 2_666 .
C10 N1 C7 108.95(18) . .
C10 N1 C13 108.57(19) . .
C7 N1 C13 111.22(19) . .
C10 N1 C16 111.29(19) . .
C7 N1 C16 109.23(19) . .
C13 N1 C16 107.58(17) . .
F1 C2 C3 121.7(3) . .
F1 C2 C1 117.7(3) . .
C3 C2 C1 120.6(3) . .
F2 C3 C2 119.8(3) . .
F2 C3 C1 117.3(3) . 2_666
C2 C3 C1 122.8(2) . 2_666
F3 C5 C6 122.4(3) . .
F3 C5 C4 115.7(2) . .
C6 C5 C4 121.9(3) . .
O2 C4 C6 121.9(3) . 2_665
O2 C4 C5 122.4(3) . .
C6 C4 C5 115.6(2) 2_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 N1 1.518(3) .
C7 C8 1.519(4) .
C7 H7A 0.9900 .
C7 H7AB 0.9900 .
C6 F4 1.332(3) .
C6 C5 1.332(4) .
C6 C4 1.472(4) 2_665
C13 C14 1.513(4) .
C13 N1 1.526(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C12 C11 1.514(4) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C11 C10 1.527(4) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C10 N1 1.513(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C9 C8 1.531(4) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C8 H8A 0.9900 .
C8 H8AB 0.9900 .
C14 C15 1.525(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.515(4) .
C16 N1 1.528(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C18 C17 1.525(4) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
F1 C2 1.307(3) .
O1 C1 1.243(3) .
C1 C3 1.440(4) 2_666
C1 C2 1.475(4) .
C2 C3 1.357(4) .
O2 C4 1.214(3) .
F2 C3 1.335(3) .
F3 C5 1.328(3) .
C5 C4 1.475(4) .
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
C12 C11 C10 N1 162.1(2) . .
N1 C7 C8 C9 177.1(2) . .
N1 C13 C14 C15 -166.0(2) . .
N1 C16 C17 C18 -173.3(2) . .
C11 C10 N1 C7 63.1(3) . .
C11 C10 N1 C13 -175.6(2) . .
C11 C10 N1 C16 -57.4(3) . .
C8 C7 N1 C10 172.3(2) . .
C8 C7 N1 C13 52.6(3) . .
C8 C7 N1 C16 -66.0(3) . .
C14 C13 N1 C10 -63.0(3) . .
C14 C13 N1 C7 56.9(3) . .
C14 C13 N1 C16 176.4(2) . .
C17 C16 N1 C10 -44.3(3) . .
C17 C16 N1 C7 -164.6(2) . .
C17 C16 N1 C13 74.5(3) . .
O1 C1 C2 F1 2.5(4) . .
C3 C1 C2 F1 179.7(3) 2_666 .
O1 C1 C2 C3 -176.3(3) . .
C3 C1 C2 C3 0.9(5) 2_666 .
F1 C2 C3 F2 1.8(5) . .
C1 C2 C3 F2 -179.5(3) . .
F1 C2 C3 C1 -179.7(3) . 2_666
C1 C2 C3 C1 -1.0(5) . 2_666
F4 C6 C5 F3 -1.8(4) . .
C4 C6 C5 F3 -176.5(2) 2_665 .
F4 C6 C5 C4 -179.1(2) . .
C4 C6 C5 C4 6.2(5) 2_665 .
F3 C5 C4 O2 -7.6(4) . .
C6 C5 C4 O2 169.9(3) . .
F3 C5 C4 C6 176.7(2) . 2_665
C6 C5 C4 C6 -5.8(4) . 2_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168334014
