Helical polycyclic hydrocarbons with open-shell singlet ground states and ambipolar redox behaviors.
Jiang, Qing; Tang, Hui; Peng, Yuchen; Hu, Zhenni; Zeng, Wangdong; Chemical science 15 (2024) 10519–10528; doi:10.1039/d4sc02116a

data_1571791
_publ_section_title
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 Helical polycyclic hydrocarbons with open-shell singlet ground states and
 ambipolar redox behaviors.
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_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              10519
_journal_page_last               10528
_journal_paper_doi               10.1039/d4sc02116a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         '2.047(Cl6 Sb), C64 H44 Cl4 O2, 1.7(Cl)'
_chemical_formula_sum            'C64 H44 Cl17.98 O2 Sb2'
_chemical_formula_weight         1725.88
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-03-01
_audit_creation_method
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Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
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_audit_update_record
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2024-03-21 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.576(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.6813(11)
_cell_length_b                   16.1611(11)
_cell_length_c                   19.3896(12)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    106.00
_cell_measurement_theta_max      66.65
_cell_measurement_theta_min      3.42
_cell_volume                     6737.1(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      106.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35329
_diffrn_reflns_theta_full        66.63
_diffrn_reflns_theta_max         66.63
_diffrn_reflns_theta_min         3.42
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.275
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1074 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.5511.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3407
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         5944
_refine_ls_number_restraints     177
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0194P)^2^+28.8725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                5275
_reflns_number_total             5944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4sc02116a2.cif
_cod_data_source_block           jq
_cod_depositor_comments
'Adding full bibliography for 1571789--1571792.cif.'
_cod_database_code               1571791
_olex2_refinement_description
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1. Restrained distances
 Sb1-Cl6 \\sim Sb1-Cl4 \\sim Sb1-Cl5 \\sim Sb1-Cl2 \\sim Sb1-Cl1 \\sim Sb1-Cl3
\\sim Sb2-Cl12 \\sim Sb2-
 Cl7 \\sim Sb2-Cl9 \\sim Sb2-Cl10 \\sim Sb2-Cl8 \\sim Sb2-Cl11
 with sigma of 0.02
 C01B-C016 \\sim C13-C01C \\sim C13-C018 \\sim C01A-C018 \\sim C20-C19 \\sim
C19-C016
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Cl2 \\sim Sb1 \\sim Cl4 \\sim Cl3 \\sim Cl1 \\sim Cl6 \\sim Cl5: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Cl10 \\sim Cl11 \\sim Sb2 \\sim Cl7 \\sim Cl9 \\sim Cl12 \\sim Cl8: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C016 \\sim C018 \\sim C01A \\sim C01B \\sim C01C \\sim C13 \\sim C19 \\sim C20:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Cl9 \\sim Cl11 \\sim Sb2 \\sim Cl7 \\sim Cl12 \\sim Cl10 \\sim Cl8: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Cl6 \\sim Sb1 \\sim Cl2 \\sim Cl4 \\sim Cl3 \\sim Cl1 \\sim Cl5: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Others
 Sof(C018)=Sof(H01C)=Sof(H01D)=Sof(C01A)=Sof(H01E)=Sof(H01F)=Sof(H01G)=
 Sof(C01C)=Sof(H01J)=Sof(H01K)=Sof(C13)=Sof(H13A)=Sof(H13B)=1-FVAR(1)
 Sof(C016)=Sof(H01A)=Sof(H01B)=Sof(C01B)=Sof(H01H)=Sof(H01I)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
 Fixed Sof: Sb1(0.25) Cl2(0.25) Cl4(0.25) Cl3(0.31) Cl1(0.25) Cl6(0.25)
 Cl5(0.25) Cl11(0.25) Sb2(0.25) Cl7(0.25) Cl9(0.33) Cl12(0.25) Cl10(0.25)
 Cl8(0.25) Cl13(0.25) Cl17(0.5) Cl14(0.1)
4.a Secondary CH2 refined with riding coordinates:
 C016(H01A,H01B), C018(H01C,H01D), C01B(H01H,H01I), C01C(H01J,H01K), C13(H13A,
 H13B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00K(H00K), C00M(H00M), C00O(H00O), C00R(H00R), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C012(H012), C014(H014), C015(H015),
 C017(H017)
4.c Idealised Me refined as rotating group:
 C01A(H01E,H01F,H01G), C20(H20A,H20B,H20C)
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_olex2_submission_special_instructions 'No special instructions were received'