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_1571790
_publ_section_title
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 Helical polycyclic hydrocarbons with open-shell singlet ground states and
 ambipolar redox behaviors.
;
_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         '4(C10 H20 K0.5 O4), C64 H44 Cl4 O2'
_chemical_formula_sum            'C104 H124 Cl4 K2 O18'
_chemical_formula_weight         1882.02
_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             2023-09-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-03-21 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                92.321(3)
_cell_angle_beta                 107.956(3)
_cell_angle_gamma                112.455(2)
_cell_formula_units_Z            2
_cell_length_a                   15.9841(7)
_cell_length_b                   17.7180(8)
_cell_length_c                   23.9712(10)
_cell_measurement_reflns_used    9033
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.76
_cell_measurement_theta_min      2.74
_cell_volume                     5871.0(5)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            85059
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         2.743
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.998
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1396 before and 0.0969 after correction.
The Ratio of minimum to maximum transmission is 0.7463.
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    1.065
_exptl_crystal_description       block
_exptl_crystal_F_000             1996
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.105
_refine_diff_density_max         1.049
_refine_diff_density_min         -1.238
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1158
_refine_ls_number_reflns         20004
_refine_ls_number_restraints     143
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0961
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1202P)^2^+22.3703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2608
_refine_ls_wR_factor_ref         0.2762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15646
_reflns_number_total             20004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02116a2.cif
_cod_data_source_block           jq1
_cod_depositor_comments
'Adding full bibliography for 1571789--1571792.cif.'
_cod_database_code               1571790
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C03N-C03L
 1.54 with sigma of 0.01
 K02-C03L \\sim K02-C03T
 with sigma of 0.01
 K02-C02V \\sim K02-C030
 with sigma of 0.01
3. Rigid bond restraints
 O017, C03W, C03F, C03Z, C03R
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O017, C03R, C03Z, C03F, C03W
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C043, C03Q, C03J, C03C, O009
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C03W \\sim C03F \\sim C03Z \\sim C03R: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
Uanis(C043) \\sim Ueq, Uanis(C03J) \\sim Ueq, Uanis(C03Z) \\sim Ueq,
Uanis(C03R) \\sim Ueq, Uanis(O017) \\sim Ueq, Uanis(C03F) \\sim Ueq,
Uanis(C033) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C043) \\sim Ueq, Uanis(C03W) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(O017) \\sim Ueq, Uanis(C03R) \\sim Ueq, Uanis(C03Z) \\sim Ueq,
Uanis(C03F) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C03Q, C043, C03J, C03C, O009, C012
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C03W, C03F, C03Z, C03R, O017
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C01K(H01A,H01C), C01Q(H01E,H01G), C01V(H01H,H01I), C027(H2,H), C02B(H3,HA),
 C02H(H4,HB), C02I(H9,HC), C02K(H02D,H02H), C02L(H02I,H02K), C02M(H02L,H02M),
 C02N(H02N,H02O), C02O(H02P,H02Q), C02P(H02R,H02S), C02Q(H02T,H02U), C02R(H5,
 HD), C02S(H02V,H02W), C02T(H02X,H02Y), C02U(H02Z,HE), C02V(H02,HF), C02W(H02A,
 H02B), C02X(H10,HG), C02Y(H1,HH), C02Z(H11,HI), C030(H03L,H03M), C032(H12,HJ),
 C033(H13,HK), C034(H14,HL), C035(H03N,H03O), C036(H15,HM), C037(H16,HN),
 C038(H03P,H03Q), C03A(H17,HO), C03B(H03A,H03B), C03C(H03C,H03D), C03D(H18,HP),
 C03E(H03R,H03S), C03F(H03,HQ), C03G(H03T,H03U), C03J(H03E,H03F), C03L(H03V,
 H03W), C03N(H03X,H03Y), C03Q(H03J,H03K), C03R(H6,HR), C03T(H03Z,HS), C03W(H7,
 HT), C03Z(H8,HU)
6.b Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00S(H00S), C01B(H01B), C01D(H01D), C01F(H01F), C01J(H01J),
 C01N(H01N), C01P(H01P), C01S(H01S), C01U(H01U), C01W(H01W), C01Y(H01Y),
 C01Z(H01Z), C020(H020), C021(H021), C022(H022), C023(H023), C024(H024),
 C025(H025), C026(H026), C028(H028), C02C(H02C), C02E(H02E), C02F(H02F),
 C02G(H02G), C02J(H02J)
6.c Idealised Me refined as rotating group:
 C03P(H03G,H03H,H03I), C043(H04A,H04B,H04C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 392 electrons were 
found in a volume of 1524\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
5[C4OH8] per Asymmetric Unit 
which account for 400 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              88103
_shelx_hkl_checksum              317
_shelx_fab_checksum              92859
_olex2_submission_special_instructions 'No special instructions were received'