#------------------------------------------------------------------------------
#$Date: 2023-04-04 12:55:37 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282285 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/86/1568622.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_1568622
loop_
_publ_author_name
'Dai, Yuyang'
'Xie, Zhuofeng'
'Bao, Manling'
'Liu, Chunmeng'
'Su, Yuanting'
_publ_section_title
;
 Multiple stable redox states and tunable ground states via the
 marriage of viologens and Chichibabin's hydrocarbon.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              3548
_journal_page_last               3553
_journal_paper_doi               10.1039/d3sc00102d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C62 H80 B2 N6, C6 H6'
_chemical_formula_sum            'C68 H86 B2 N6'
_chemical_formula_weight         1009.04
_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     dual
_audit_creation_date             2021-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-07 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                69.242(2)
_cell_angle_beta                 84.549(2)
_cell_angle_gamma                77.162(2)
_cell_formula_units_Z            1
_cell_length_a                   9.3498(8)
_cell_length_b                   11.4321(10)
_cell_length_c                   15.5813(14)
_cell_measurement_reflns_used    9333
_cell_measurement_temperature    131(2)
_cell_measurement_theta_max      53.86
_cell_measurement_theta_min      5.02
_cell_volume                     1518.2(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      131.0
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22537
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.964
_diffrn_reflns_theta_min         5.019
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6078
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1238 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.8098.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5342
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0550
_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)+(0.0659P)²+0.6760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5080
_reflns_number_total             5342
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc00102d2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1568622--1568625.cif.'
_cod_database_code               1568622
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C34_$1-C33 = C34_$1-C32_$1 = C33_$1-C32_$1 = C34-C33_$1 = C34-C32 = C33-C32
 1.395 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C29(H29), C26(H26), C20(H20), C23(H23)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C18(H18), C19(H19), C14(H14), C16(H16), C15(H15), C11(H11), C9(H9),
 C3(H3), C5(H5), C4(H4), C10(H10), C34(H34), C32(H32), C33(H33)
3.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C22(H22A,H22B,H22C), C31(H31A,H31B,H31C), C21(H21A,H21B,
 H21C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.15753(11) 0.47431(10) 0.21424(7) 0.0196(2) Uani 1 1 d . . . . .
N3 N 0.15545(12) 0.24447(10) 0.32750(7) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.36594(12) 0.32296(10) 0.21929(7) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.02514(14) 0.55095(12) 0.23561(9) 0.0211(3) Uani 1 1 d . . . . .
C17 C 0.03040(13) 0.04652(12) 0.46715(8) 0.0198(3) Uani 1 1 d . . . . .
C13 C 0.26390(14) 0.53103(13) 0.15346(9) 0.0227(3) Uani 1 1 d . . . . .
H13 H 0.251294 0.618674 0.116267 0.027 Uiso 1 1 calc R . . . .
C18 C 0.14237(14) 0.02186(12) 0.40084(9) 0.0226(3) Uani 1 1 d . . . . .
H18 H 0.176961 -0.063715 0.402817 0.027 Uiso 1 1 calc R . . . .
C7 C 0.49037(14) 0.22134(12) 0.25358(9) 0.0218(3) Uani 1 1 d . . . . .
C19 C 0.19906(14) 0.11502(12) 0.33683(9) 0.0233(3) Uani 1 1 d . . . . .
H19 H 0.272369 0.092023 0.295845 0.028 Uiso 1 1 calc R . . . .
C14 C 0.38579(14) 0.44221(13) 0.15617(9) 0.0226(3) Uani 1 1 d . . . . .
H14 H 0.472637 0.457358 0.120835 0.027 Uiso 1 1 calc R . . . .
C16 C -0.01033(14) 0.18172(12) 0.45607(9) 0.0223(3) Uani 1 1 d . . . . .
H16 H -0.081585 0.207257 0.497094 0.027 Uiso 1 1 calc R . . . .
C8 C 0.55263(15) 0.14367(13) 0.20188(9) 0.0251(3) Uani 1 1 d . . . . .
C12 C 0.54892(15) 0.20415(13) 0.33833(9) 0.0252(3) Uani 1 1 d . . . . .
C15 C 0.04817(14) 0.27156(12) 0.39066(9) 0.0228(3) Uani 1 1 d . . . . .
H15 H 0.015227 0.358013 0.386941 0.027 Uiso 1 1 calc R . . . .
C2 C 0.03255(16) 0.61454(13) 0.29698(9) 0.0255(3) Uani 1 1 d . . . . .
C6 C -0.10698(15) 0.55846(13) 0.19668(9) 0.0259(3) Uani 1 1 d . . . . .
C11 C 0.67412(16) 0.10965(15) 0.36798(10) 0.0320(3) Uani 1 1 d . . . . .
H11 H 0.715602 0.096461 0.424838 0.038 Uiso 1 1 calc R . . . .
C29 C 0.48620(16) 0.15742(15) 0.11243(10) 0.0312(3) Uani 1 1 d . . . . .
H29 H 0.392763 0.222753 0.103562 0.037 Uiso 1 1 calc R . . . .
C26 C 0.48149(16) 0.28427(15) 0.39744(10) 0.0304(3) Uani 1 1 d . . . . .
H26 H 0.389195 0.340883 0.367053 0.036 Uiso 1 1 calc R . . . .
C9 C 0.67820(16) 0.05081(14) 0.23457(10) 0.0307(3) Uani 1 1 d . . . . .
H9 H 0.722474 -0.002152 0.200138 0.037 Uiso 1 1 calc R . . . .
C3 C -0.09842(17) 0.68416(14) 0.32071(10) 0.0326(3) Uani 1 1 d . . . . .
H3 H -0.096565 0.727671 0.362316 0.039 Uiso 1 1 calc R . . . .
C5 C -0.23420(16) 0.62936(15) 0.22295(10) 0.0330(3) Uani 1 1 d . . . . .
H5 H -0.325486 0.635631 0.197886 0.040 Uiso 1 1 calc R . . . .
C4 C -0.22999(17) 0.69049(15) 0.28459(11) 0.0350(4) Uani 1 1 d . . . . .
H4 H -0.318105 0.737055 0.302142 0.042 Uiso 1 1 calc R . . . .
C20 C 0.17697(17) 0.60879(15) 0.33724(10) 0.0322(3) Uani 1 1 d . . . . .
H20 H 0.255514 0.552587 0.313265 0.039 Uiso 1 1 calc R . . . .
C23 C -0.11211(16) 0.49217(17) 0.12826(11) 0.0350(4) Uani 1 1 d . . . . .
H23 H -0.010701 0.475671 0.102291 0.042 Uiso 1 1 calc R . . . .
C10 C 0.73946(17) 0.03462(15) 0.31672(11) 0.0342(4) Uani 1 1 d . . . . .
H10 H 0.826168 -0.027952 0.337662 0.041 Uiso 1 1 calc R . . . .
B1 B 0.22077(16) 0.34169(14) 0.25763(10) 0.0202(3) Uani 1 1 d . . . . .
C30 C 0.5877(2) 0.20470(19) 0.03060(11) 0.0442(4) Uani 1 1 d . . . . .
H30A H 0.606774 0.287001 0.027524 0.066 Uiso 1 1 calc GR . . . .
H30B H 0.540968 0.215073 -0.026066 0.066 Uiso 1 1 calc GR . . . .
H30C H 0.680522 0.142398 0.037767 0.066 Uiso 1 1 calc GR . . . .
C22 C 0.1752(2) 0.54917(17) 0.44213(11) 0.0407(4) Uani 1 1 d . . . . .
H22A H 0.095876 0.599877 0.467620 0.061 Uiso 1 1 calc GR . . . .
H22B H 0.269374 0.547818 0.465643 0.061 Uiso 1 1 calc GR . . . .
H22C H 0.159340 0.461666 0.460237 0.061 Uiso 1 1 calc GR . . . .
C31 C 0.4486(2) 0.03133(19) 0.11677(13) 0.0478(4) Uani 1 1 d . . . . .
H31A H 0.539186 -0.033070 0.121639 0.072 Uiso 1 1 calc GR . . . .
H31B H 0.397434 0.044871 0.060937 0.072 Uiso 1 1 calc GR . . . .
H31C H 0.385246 0.001710 0.170487 0.072 Uiso 1 1 calc GR . . . .
C21 C 0.2156(2) 0.74090(18) 0.30545(14) 0.0492(5) Uani 1 1 d . . . . .
H21A H 0.225575 0.772815 0.238378 0.074 Uiso 1 1 calc GR . . . .
H21B H 0.308430 0.734955 0.332638 0.074 Uiso 1 1 calc GR . . . .
H21C H 0.137602 0.799659 0.324958 0.074 Uiso 1 1 calc GR . . . .
C24 C -0.1569(2) 0.36302(18) 0.17456(14) 0.0524(5) Uani 1 1 d . . . . .
H24A H -0.088892 0.309167 0.224027 0.079 Uiso 1 1 calc GR . . . .
H24B H -0.153875 0.321039 0.129229 0.079 Uiso 1 1 calc GR . . . .
H24C H -0.256679 0.376093 0.200087 0.079 Uiso 1 1 calc GR . . . .
C25 C -0.2132(2) 0.5748(2) 0.04821(12) 0.0502(5) Uani 1 1 d . . . . .
H25A H -0.314665 0.588376 0.071028 0.075 Uiso 1 1 calc GR . . . .
H25B H -0.205775 0.531667 0.003217 0.075 Uiso 1 1 calc GR . . . .
H25C H -0.183941 0.657446 0.019028 0.075 Uiso 1 1 calc GR . . . .
C27 C 0.4376(3) 0.1997(2) 0.49247(14) 0.0730(7) Uani 1 1 d . . . . .
H27A H 0.374968 0.145295 0.485719 0.109 Uiso 1 1 calc GR . . . .
H27B H 0.383812 0.253592 0.526635 0.109 Uiso 1 1 calc GR . . . .
H27C H 0.525960 0.145952 0.525901 0.109 Uiso 1 1 calc GR . . . .
C34 C 0.9731(3) -0.1023(2) 0.07317(17) 0.0858(10) Uani 1 1 d D . . . .
H34 H 0.953873 -0.174028 0.123551 0.103 Uiso 1 1 calc R . . . .
C28 C 0.5802(2) 0.3703(3) 0.4013(2) 0.0757(8) Uani 1 1 d . . . . .
H28A H 0.673221 0.318184 0.429297 0.114 Uiso 1 1 calc GR . . . .
H28B H 0.532283 0.422553 0.438041 0.114 Uiso 1 1 calc GR . . . .
H28C H 0.599066 0.426152 0.338897 0.114 Uiso 1 1 calc GR . . . .
C32 C 1.0106(3) -0.0020(3) 0.09097(16) 0.0881(9) Uani 1 1 d D . . . .
H32 H 1.017632 -0.004285 0.151991 0.106 Uiso 1 1 calc R . . . .
C33 C 1.0375(3) 0.1018(2) 0.01554(19) 0.0931(10) Uani 1 1 d D . . . .
H33 H 1.063061 0.172464 0.024634 0.112 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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'
B B 0.0073 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 '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
_geom_angle_publ_flag
C13 N1 C1 120.96(10) . . ?
C13 N1 B1 107.61(11) . . ?
B1 N1 C1 130.39(11) . . ?
C19 N3 B1 121.32(11) . . ?
C15 N3 C19 115.39(11) . . ?
C15 N3 B1 123.28(11) . . ?
C14 N2 C7 120.38(10) . . ?
C14 N2 B1 107.23(11) . . ?
B1 N2 C7 129.55(11) . . ?
C2 C1 N1 118.30(12) . . ?
C6 C1 N1 119.62(11) . . ?
C6 C1 C2 122.08(12) . . ?
C17 C17 C18 124.10(15) 2_556 . ?
C17 C17 C16 123.69(15) 2_556 . ?
C18 C17 C16 112.22(11) . . ?
C14 C13 N1 109.42(11) . . ?
C19 C18 C17 122.78(12) . . ?
C8 C7 N2 119.85(12) . . ?
C8 C7 C12 121.49(12) . . ?
C12 C7 N2 118.65(12) . . ?
C18 C19 N3 123.33(12) . . ?
C13 C14 N2 109.88(11) . . ?
C15 C16 C17 122.97(12) . . ?
C7 C8 C29 121.93(12) . . ?
C9 C8 C7 118.38(13) . . ?
C9 C8 C29 119.70(13) . . ?
C7 C12 C26 122.84(12) . . ?
C11 C12 C7 117.75(13) . . ?
C11 C12 C26 119.41(12) . . ?
C16 C15 N3 123.31(12) . . ?
C1 C2 C20 121.88(12) . . ?
C3 C2 C1 117.82(13) . . ?
C3 C2 C20 120.31(13) . . ?
C1 C6 C23 121.32(12) . . ?
C5 C6 C1 117.52(13) . . ?
C5 C6 C23 121.16(13) . . ?
C10 C11 C12 121.57(14) . . ?
C8 C29 C30 111.27(12) . . ?
C8 C29 C31 111.13(13) . . ?
C30 C29 C31 110.80(13) . . ?
C12 C26 C27 110.85(14) . . ?
C28 C26 C12 111.50(13) . . ?
C28 C26 C27 113.1(2) . . ?
C10 C9 C8 120.91(14) . . ?
C4 C3 C2 120.94(14) . . ?
C4 C5 C6 121.39(14) . . ?
C3 C4 C5 120.23(14) . . ?
C2 C20 C22 111.74(13) . . ?
C2 C20 C21 110.95(13) . . ?
C21 C20 C22 111.39(13) . . ?
C6 C23 C24 111.69(13) . . ?
C6 C23 C25 112.46(14) . . ?
C25 C23 C24 109.97(14) . . ?
C11 C10 C9 119.86(14) . . ?
N1 B1 N3 128.26(12) . . ?
N2 B1 N1 105.86(11) . . ?
N2 B1 N3 125.87(12) . . ?
C32 C34 C33 122.6(2) . 2_755 ?
C34 C32 C33 117.2(2) . . ?
C34 C33 C32 120.2(2) 2_755 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4343(17) . ?
N1 C13 1.4067(16) . ?
N1 B1 1.4340(18) . ?
N3 C19 1.4028(17) . ?
N3 C15 1.4004(17) . ?
N3 B1 1.4530(18) . ?
N2 C7 1.4374(17) . ?
N2 C14 1.4098(17) . ?
N2 B1 1.4326(18) . ?
C1 C2 1.4055(19) . ?
C1 C6 1.3998(19) . ?
C17 C17 1.374(2) 2_556 ?
C17 C18 1.4536(18) . ?
C17 C16 1.4579(18) . ?
C13 C14 1.3401(19) . ?
C18 C19 1.3444(19) . ?
C7 C8 1.4015(19) . ?
C7 C12 1.4099(19) . ?
C16 C15 1.3396(19) . ?
C8 C29 1.5228(19) . ?
C8 C9 1.393(2) . ?
C12 C11 1.392(2) . ?
C12 C26 1.522(2) . ?
C2 C3 1.400(2) . ?
C2 C20 1.521(2) . ?
C6 C5 1.398(2) . ?
C6 C23 1.520(2) . ?
C11 C10 1.381(2) . ?
C29 C30 1.526(2) . ?
C29 C31 1.535(2) . ?
C26 C27 1.530(3) . ?
C26 C28 1.509(2) . ?
C9 C10 1.387(2) . ?
C3 C4 1.378(2) . ?
C5 C4 1.381(2) . ?
C20 C22 1.532(2) . ?
C20 C21 1.528(2) . ?
C23 C24 1.529(3) . ?
C23 C25 1.527(2) . ?
C34 C32 1.3924(7) . ?
C34 C33 1.3930(7) 2_755 ?
C32 C33 1.3934(7) . ?
