#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/20/4032011.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_4032011
loop_
_publ_author_name
'Zhang, Xiaoping'
'Clennan, Edward L.'
'Arulsamy, Navamoney'
'Weber, Rachael'
'Weber, Jacob'
_publ_section_title
;
 Synthesis, Structure, and Photochemical Behavior of [5]Heli-viologen
 Isomers.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5474
_journal_page_last               5486
_journal_paper_doi               10.1021/acs.joc.6b00835
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C24 H18 N2, 2(B F4), C2 H3 N'
_chemical_formula_sum            'C24 H21 B2 F8 N3'
_chemical_formula_weight         525.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 115.335(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.7449(6)
_cell_length_b                   19.7482(6)
_cell_length_c                   11.4956(3)
_cell_measurement_reflns_used    8726
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.77
_cell_measurement_theta_min      2.75
_cell_volume                     4666.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39271
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.727
_diffrn_reflns_theta_min         2.055
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.7058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         9306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0745
_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)+(0.1517P)²+2.6571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2156
_refine_ls_wR_factor_ref         0.2443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6598
_reflns_number_total             9306
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00835_si_002.cif
_cod_data_source_block           xz03a
_cod_database_code               4032011
_shelx_shelxl_version_number     2014/7
_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   0.935
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66450(7) 0.13857(7) 0.82249(13) 0.0238(3) Uani 1 1 d . . . . .
H1A H 0.6770 0.1626 0.9011 0.029 Uiso 1 1 calc R U . . .
C2 C 0.68501(8) 0.07367(8) 0.82384(14) 0.0273(3) Uani 1 1 d . . . . .
H2A H 0.7129 0.0532 0.9032 0.033 Uiso 1 1 calc R U . . .
N1 N 0.66580(7) 0.03770(7) 0.71176(13) 0.0276(3) Uani 1 1 d . . . . .
C3 C 0.68646(11) -0.03367(9) 0.71754(19) 0.0397(4) Uani 1 1 d . . . . .
H3A H 0.7112 -0.0471 0.8076 0.060 Uiso 1 1 calc R U . . .
H3B H 0.6480 -0.0627 0.6773 0.060 Uiso 1 1 calc R U . . .
H3C H 0.7139 -0.0386 0.6715 0.060 Uiso 1 1 calc R U . . .
C4 C 0.63161(8) 0.06640(8) 0.59903(14) 0.0264(3) Uani 1 1 d . . . . .
H4A H 0.6195 0.0404 0.5227 0.032 Uiso 1 1 calc R U . . .
C5 C 0.61292(7) 0.13461(7) 0.59016(12) 0.0229(2) Uani 1 1 d . . . . .
C6 C 0.58797(8) 0.16702(8) 0.46750(13) 0.0263(3) Uani 1 1 d . . . . .
H6A H 0.5767 0.1413 0.3911 0.032 Uiso 1 1 calc R U . . .
C7 C 0.58072(7) 0.23507(8) 0.46212(12) 0.0254(3) Uani 1 1 d . . . . .
H7A H 0.5702 0.2584 0.3834 0.030 Uiso 1 1 calc R U . . .
C8 C 0.58891(7) 0.27183(7) 0.57516(12) 0.0224(2) Uani 1 1 d . . . . .
C9 C 0.58737(7) 0.34296(8) 0.56951(13) 0.0258(3) Uani 1 1 d . . . . .
H9A H 0.5792 0.3649 0.4905 0.031 Uiso 1 1 calc R U . . .
N2 N 0.59702(7) 0.37984(7) 0.67152(12) 0.0274(3) Uani 1 1 d . . . . .
C10 C 0.60330(13) 0.45436(9) 0.6626(2) 0.0446(5) Uani 1 1 d . . . . .
H10A H 0.6103 0.4754 0.7447 0.067 Uiso 1 1 calc R U . . .
H10B H 0.6404 0.4644 0.6432 0.067 Uiso 1 1 calc R U . . .
H10C H 0.5634 0.4724 0.5940 0.067 Uiso 1 1 calc R U . . .
C11 C 0.59990(7) 0.35073(7) 0.78417(13) 0.0252(3) Uani 1 1 d . . . . .
C12 C 0.60642(10) 0.39382(9) 0.88786(16) 0.0336(3) Uani 1 1 d . . . . .
H12A H 0.6104 0.4414 0.8813 0.040 Uiso 1 1 calc R U . . .
C13 C 0.60686(9) 0.36619(9) 0.99695(15) 0.0338(3) Uani 1 1 d . . . . .
H13A H 0.6152 0.3943 1.0694 0.041 Uiso 1 1 calc R U . . .
C14 C 0.59504(7) 0.29583(8) 1.00409(14) 0.0266(3) Uani 1 1 d . . . . .
C15 C 0.58786(8) 0.27008(9) 1.11214(14) 0.0308(3) Uani 1 1 d . . . . .
H15A H 0.5947 0.2989 1.1830 0.037 Uiso 1 1 calc R U . . .
C16 C 0.57107(8) 0.20376(9) 1.11488(15) 0.0322(3) Uani 1 1 d . . . . .
H16A H 0.5679 0.1862 1.1889 0.039 Uiso 1 1 calc R U . . .
C17 C 0.55856(7) 0.16143(9) 1.00843(14) 0.0280(3) Uani 1 1 d . . . . .
H17A H 0.5446 0.1161 1.0089 0.034 Uiso 1 1 calc R U . . .
C18 C 0.56645(7) 0.18535(8) 0.90353(13) 0.0241(3) Uani 1 1 d . . . . .
H18A H 0.5575 0.1564 0.8319 0.029 Uiso 1 1 calc R U . . .
C19 C 0.58770(6) 0.25227(8) 0.90073(12) 0.0226(2) Uani 1 1 d . . . . .
C20 C 0.59727(6) 0.27962(7) 0.79296(12) 0.0218(2) Uani 1 1 d . . . . .
C21 C 0.60218(6) 0.23972(7) 0.69313(12) 0.0205(2) Uani 1 1 d . . . . .
C22 C 0.62454(7) 0.17044(7) 0.70439(12) 0.0212(2) Uani 1 1 d . . . . .
B1 B 0.28317(10) 0.41301(10) 0.06811(19) 0.0342(4) Uani 1 1 d . . . . .
F1 F 0.21925(6) 0.39426(8) -0.00958(12) 0.0499(3) Uani 1 1 d . . . . .
F2 F 0.29112(8) 0.41718(9) 0.19493(13) 0.0591(4) Uani 1 1 d . . . . .
F3 F 0.32436(8) 0.36282(8) 0.06184(17) 0.0613(4) Uani 1 1 d . . . . .
F4 F 0.29730(8) 0.47394(8) 0.02907(16) 0.0688(5) Uani 1 1 d . . . . .
B2 B 0.0000 0.50976(15) 0.2500 0.0372(6) Uani 1 2 d S T P . .
F5 F 0.0286(6) 0.5612(4) 0.2171(9) 0.074(3) Uani 0.4 1 d . . P A 1
F6 F 0.0468(3) 0.4729(3) 0.3356(6) 0.0674(17) Uani 0.4 1 d . . P A 1
F5A F 0.0638(3) 0.5074(8) 0.3174(11) 0.122(5) Uani 0.3 1 d . . P A 2
F6A F -0.0212(5) 0.4517(3) 0.2959(11) 0.110(3) Uani 0.3 1 d . . P A 2
F5C F 0.0256(6) 0.5512(7) 0.1814(12) 0.080(4) Uani 0.3 1 d . . P A 3
F6C F 0.0206(7) 0.4964(7) 0.3734(7) 0.133(5) Uani 0.3 1 d . . P A 3
B3 B 0.5000 0.41754(15) 0.2500 0.0431(7) Uani 1 2 d S T P . .
F7 F 0.5000 0.35095(10) 0.2500 0.0785(8) Uani 1 2 d S T P B .
F8 F 0.4642(2) 0.4555(2) 0.1551(4) 0.0465(10) Uani 0.5 1 d . . P B -1
F8A F 0.4654(2) 0.41675(17) 0.3414(4) 0.0793(12) Uani 0.5 1 d . . P B -1
F9 F 0.5567(2) 0.4463(3) 0.3332(6) 0.082(2) Uani 0.5 1 d . . P B -1
N3 N 0.25435(9) 0.17099(11) 0.35254(18) 0.0468(4) Uani 1 1 d . . . . .
C23 C 0.25682(8) 0.20250(9) 0.27138(16) 0.0336(3) Uani 1 1 d . . . . .
C24 C 0.25980(9) 0.24255(11) 0.16848(18) 0.0405(4) Uani 1 1 d . . . . .
H24A H 0.2717 0.2892 0.1980 0.061 Uiso 1 1 calc R U . . .
H24B H 0.2172 0.2422 0.0942 0.061 Uiso 1 1 calc R U . . .
H24C H 0.2925 0.2234 0.1436 0.061 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 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'
B B 0.0013 0.0007 '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'
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
C2 C1 C22 120.33(13) . .
C2 C1 H1A 119.8 . .
C22 C1 H1A 119.8 . .
C1 C2 N1 120.53(13) . .
C1 C2 H2A 119.7 . .
N1 C2 H2A 119.7 . .
C4 N1 C2 121.19(13) . .
C4 N1 C3 119.72(14) . .
C2 N1 C3 119.03(13) . .
N1 C3 H3A 109.5 . .
N1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
N1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
N1 C4 C5 121.09(13) . .
N1 C4 H4A 119.5 . .
C5 C4 H4A 119.5 . .
C4 C5 C22 118.86(12) . .
C4 C5 C6 118.86(12) . .
C22 C5 C6 122.06(13) . .
C7 C6 C5 118.70(12) . .
C7 C6 H6A 120.6 . .
C5 C6 H6A 120.6 . .
C6 C7 C8 119.83(12) . .
C6 C7 H7A 120.1 . .
C8 C7 H7A 120.1 . .
C9 C8 C21 119.05(12) . .
C9 C8 C7 118.32(12) . .
C21 C8 C7 122.52(13) . .
N2 C9 C8 121.34(12) . .
N2 C9 H9A 119.3 . .
C8 C9 H9A 119.3 . .
C9 N2 C11 121.56(13) . .
C9 N2 C10 118.06(13) . .
C11 N2 C10 120.37(13) . .
N2 C10 H10A 109.5 . .
N2 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N2 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N2 C11 C20 119.40(12) . .
N2 C11 C12 118.66(13) . .
C20 C11 C12 121.93(13) . .
C13 C12 C11 119.28(15) . .
C13 C12 H12A 120.4 . .
C11 C12 H12A 120.4 . .
C12 C13 C14 121.07(14) . .
C12 C13 H13A 119.5 . .
C14 C13 H13A 119.5 . .
C15 C14 C19 120.08(14) . .
C15 C14 C13 119.79(14) . .
C19 C14 C13 120.07(13) . .
C16 C15 C14 120.16(14) . .
C16 C15 H15A 119.9 . .
C14 C15 H15A 119.9 . .
C15 C16 C17 120.21(14) . .
C15 C16 H16A 119.9 . .
C17 C16 H16A 119.9 . .
C18 C17 C16 120.30(15) . .
C18 C17 H17A 119.9 . .
C16 C17 H17A 119.9 . .
C17 C18 C19 121.02(13) . .
C17 C18 H18A 119.5 . .
C19 C18 H18A 119.5 . .
C18 C19 C14 117.86(12) . .
C18 C19 C20 123.08(12) . .
C14 C19 C20 118.87(13) . .
C11 C20 C21 117.97(12) . .
C11 C20 C19 117.27(12) . .
C21 C20 C19 124.73(13) . .
C8 C21 C20 117.70(12) . .
C8 C21 C22 115.77(11) . .
C20 C21 C22 126.34(11) . .
C5 C22 C1 117.12(12) . .
C5 C22 C21 118.14(11) . .
C1 C22 C21 124.24(12) . .
F4 B1 F3 110.64(17) . .
F4 B1 F1 110.53(17) . .
F3 B1 F1 108.65(16) . .
F4 B1 F2 110.34(18) . .
F3 B1 F2 107.97(17) . .
F1 B1 F2 108.63(16) . .
F6C B2 F6C 156.8(13) . 2
F6 B2 F6 112.9(6) 2 .
F5A B2 F5A 176.0(14) . 2
F6 B2 F5 107.1(6) 2 2
F6 B2 F5 122.7(5) . 2
F6 B2 F5 122.7(5) 2 .
F6 B2 F5 107.1(6) . .
F5 B2 F5 81.8(9) 2 .
F6C B2 F5C 63.9(9) . 2
F6C B2 F5C 132.2(7) 2 2
F6C B2 F5C 132.2(7) . .
F6C B2 F5C 63.9(9) 2 .
F5C B2 F5C 109.7(11) 2 .
F5A B2 F6A 74.3(6) . 2
F5A B2 F6A 102.4(9) 2 2
F5A B2 F6A 102.4(9) . .
F5A B2 F6A 74.3(6) 2 .
F6A B2 F6A 73.3(7) 2 .
B2 F5 F5 49.1(5) . 2
B2 F5A F6A 55.8(5) . 2
B2 F6A F5A 49.9(4) . 2
B2 F6A F6A 53.4(4) . 2
F5A F6A F6A 79.0(8) 2 2
B2 F5C F6C 54.5(6) . 2
B2 F6C F5C 61.6(6) . 2
F8 B3 F7 125.7(2) . .
F8 B3 F9 114.8(3) . .
F7 B3 F9 114.7(3) . .
F8 B3 F8A 105.0(3) . .
F7 B3 F8A 89.43(16) . .
F9 B3 F8A 97.5(3) . .
N3 C23 C24 179.8(2) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.362(2) .
C1 C22 1.4175(18) .
C1 H1A 0.9500 .
C2 N1 1.369(2) .
C2 H2A 0.9500 .
N1 C4 1.320(2) .
N1 C3 1.478(2) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 C5 1.403(2) .
C4 H4A 0.9500 .
C5 C22 1.4136(18) .
C5 C6 1.4266(19) .
C6 C7 1.352(2) .
C6 H6A 0.9500 .
C7 C8 1.4295(18) .
C7 H7A 0.9500 .
C8 C9 1.406(2) .
C8 C21 1.4079(18) .
C9 N2 1.3167(19) .
C9 H9A 0.9500 .
N2 C11 1.3926(18) .
N2 C10 1.486(2) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C20 1.411(2) .
C11 C12 1.420(2) .
C12 C13 1.364(2) .
C12 H12A 0.9500 .
C13 C14 1.424(2) .
C13 H13A 0.9500 .
C14 C15 1.415(2) .
C14 C19 1.4177(19) .
C15 C16 1.368(3) .
C15 H15A 0.9500 .
C16 C17 1.407(2) .
C16 H16A 0.9500 .
C17 C18 1.3765(19) .
C17 H17A 0.9500 .
C18 C19 1.412(2) .
C18 H18A 0.9500 .
C19 C20 1.4507(18) .
C20 C21 1.4353(18) .
C21 C22 1.4459(19) .
B1 F4 1.370(2) .
B1 F3 1.387(2) .
B1 F1 1.392(2) .
B1 F2 1.393(2) .
B2 F6C 1.316(7) .
B2 F6C 1.316(7) 2
B2 F6 1.316(4) 2
B2 F6 1.316(4) .
B2 F5A 1.321(7) .
B2 F5A 1.321(7) 2
B2 F5 1.345(8) 2
B2 F5 1.345(8) .
B2 F5C 1.422(11) 2
B2 F5C 1.422(11) .
B2 F6A 1.429(7) 2
B2 F6A 1.429(7) .
F5 F5 1.76(2) 2
F5A F6A 1.663(12) 2
F6A F5A 1.663(12) 2
F6A F6A 1.706(18) 2
F5C F6C 1.45(2) 2
F6C F5C 1.45(2) 2
B3 F8 1.286(4) .
B3 F7 1.315(3) .
B3 F9 1.358(5) .
B3 F8A 1.560(3) .
N3 C23 1.143(2) .
C23 C24 1.449(2) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 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
C19 C20 C21 C22 -26.8(2)
C11 C20 C21 C22 155.25(13)
C5 C22 C21 C20 166.46(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094722
