Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201° end-to-end twist: "one-pot" synthesis and chiral resolution.
Sun, Zhitao; Fan, Wei; Han, Yi; Yuan, Wei; Ni, Yong; Wang, Jinyi; Wei, Haipeng; Zhao, Yanli; Sun, Zhe; Wu, Jishan; Chemical science 14 (2023) 7922–7927; doi:10.1039/d3sc02285d

data_1569350
_publ_section_title
;
 Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201&#xb0;
 end-to-end twist: "one-pot" synthesis and chiral resolution.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              7922
_journal_page_last               7927
_journal_paper_doi               10.1039/d3sc02285d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         '0.5(C H2 Cl2), C62 H46'
_chemical_formula_sum            'C62.5 H47 Cl'
_chemical_formula_weight         833.45
_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             2023-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-14 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                92.959(2)
_cell_angle_beta                 105.254(2)
_cell_angle_gamma                90.553(2)
_cell_formula_units_Z            4
_cell_length_a                   14.1114(8)
_cell_length_b                   17.2949(10)
_cell_length_c                   19.1195(11)
_cell_measurement_reflns_used    9434
_cell_measurement_temperature    104(2)
_cell_measurement_theta_max      72.925
_cell_measurement_theta_min      4.521
_cell_volume                     4494.5(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      104.0
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.951
_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  0.0700
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            93144
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.204
_diffrn_reflns_theta_min         2.399
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1382 before and 0.0994 after correction. The Ratio of minimum to maximum transmission is 0.8211. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic dark green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             1756
_exptl_crystal_size_max          0.499
_exptl_crystal_size_mid          0.496
_exptl_crystal_size_min          0.374
_refine_diff_density_max         1.412
_refine_diff_density_min         -1.082
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1156
_refine_ls_number_reflns         17143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.1218
_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/[\s^2^(Fo^2^)+(0.1216P)^2^+16.6797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3018
_refine_ls_wR_factor_ref         0.3038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16269
_reflns_number_total             17143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02285d10.cif
_cod_data_source_block           szt20221228_0m
_cod_depositor_comments
'Adding full bibliography for 1569350--1569353.cif.'
_cod_original_formula_sum        'C62.50 H47 Cl'
_cod_database_code               1569350
_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.a Secondary CH2 refined with riding coordinates:
 C03G(H0AA,HA)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00E(H00E), C00J(H00J), C00T(H00T), C00Z(H00Z), C013(H013),
 C016(H016), C018(H018), C01A(H01A), C01B(H01B), C01C(H01C), C01D(H01D),
 C01F(H01F), C01G(H01G), C01H(H01H), C01K(H01K), C01L(H01L), C01M(H01M),
 C01N(H01N), C01O(H01O), C01R(H01R), C01S(H01S), C01T(H01T), C01U(H01U),
 C01V(H01V), C01W(H01W), C01Y(H01Y), C01Z(H01Z), C020(H020), C022(H022),
 C025(H025), C026(H026), C027(H027), C028(H028), C029(H029), C02A(H02F),
 C02C(H02D), C02D(H02E), C02E(H02H), C02G(H02G), C02H(H02J), C02I(H02I),
 C02J(H02L), C02K(H02K), C02L(H02M), C02M(H02P), C02N(H02N), C02O(H02O),
 C02R(H02R), C02W(H02W), C02Y(H02Y), C034(H034), C035(H035), C03A(H03J),
 C03B(H03K), C03E(H03Z)
2.c Idealised Me refined as rotating group:
 C01X(H01E,H01I,H01J), C024(H02A,H02B,H02C), C02V(H02Q,H02S,H02T), C030(H03A,
 H03B,H03C), C032(H03R,H03S,H03T), C033(H03U,H03V,H03W), C036(H03X,H03Y,H),
 C037(H03D,H03E,H03F), C038(H03G,H03H,H03I), C03H(H03L,H03M,H03N), C03I(H03O,
 H03P,H03Q), C03J(H03,HB,HC)
;
_olex2_submission_special_instructions 'No special instructions were received'