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_1569352
_publ_section_title
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 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         '2(C58 H54)'
_chemical_formula_sum            'C116 H108'
_chemical_formula_weight         1502.02
_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
_audit_creation_date             2022-08-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-14 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.328(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.1031(13)
_cell_length_b                   18.2874(6)
_cell_length_c                   30.6172(10)
_cell_measurement_reflns_used    9699
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.78
_cell_measurement_theta_min      2.81
_cell_volume                     17357.8(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1129
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            154547
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.970
_diffrn_reflns_theta_max         66.970
_diffrn_reflns_theta_min         2.805
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1580 before and 0.1081 after correction.
The Ratio of minimum to maximum transmission is 0.6168.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic dark red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       block
_exptl_crystal_F_000             6432
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.066
_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     1080
_refine_ls_number_reflns         15370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0746P)^2^+17.4962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12636
_reflns_number_total             15370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02285d10.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 1569350--1569353.cif.'
_cod_database_code               1569352
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.808
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H02L(0.65) H02M(0.65) H02N(0.35) H02O(0.35) C035(0.65) H03G(0.65)
 H03H(0.65) C038(0.65) H03L(0.65) H03M(0.65) H03N(0.65) C1(0.35) H1A(0.35)
 H1B(0.35) H1C(0.35) C2(0.35) H2A(0.35) H2B(0.35)
3.a Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C01E(H01H,H01J), C01N(H01A,H01C), C01S(H01K,H01M), C01X(H01E,
 H01F), C023(H02A,H02B), C02C(H02D,H02E), C02I(H1,HB), C02L(H02L,H02M),
 C02L(H02N,H02O), C02V(H7,HI), C02X(H9,HL), C035(H03G,H03H), C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00J(H00J), C00K(H00K), C00M(H00M), C00T(H00T), C00V(H00V),
 C00Z(H00Z), C011(H011), C012(H012), C013(H013), C015(H015), C019(H019),
 C01B(H01B), C01C(H01G), C01D(H01D), C01I(H01I), C01L(H01L), C01Q(H01Q),
 C01R(H01R), C01T(H01T), C01V(H01V), C01Z(H01Z), C020(H020), C021(H021),
 C022(H022), C024(H024), C026(H026), C029(H029), C02B(H02C), C02E(H02F),
 C02H(H02J), C02J(H02K), C02M(H02P), C02O(H3), C02T(H5), C02Z(H02Z)
3.c Idealised Me refined as rotating group:
 C02A(H02,H,HA), C02G(H02G,H02H,H02I), C02K(H2,HC,HD), C02N(H02Q,H02R,H02S),
 C02Q(H4,HE,HF), C02R(H02T,H02U,H02V), C02U(H6,HG,HH), C02W(H8,HJ,HK),
 C02Y(H02W,H02X,H02Y), C031(H03A,H03B,H03C), C032(H03D,H03E,H03F), C033(H03O,
 H03P,H03Q), C034(H03R,H03S,H03T), C036(H03I,H03J,H03K), C037(H03U,H03V,H03W),
 C038(H03L,H03M,H03N), C1(H1A,H1B,H1C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              88458
_shelx_hkl_checksum              28219
_shelx_fab_checksum              38298
_olex2_submission_special_instructions 'No special instructions were received'