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_1569351
_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         'C110 H102, 4(C7 H8)'
_chemical_formula_sum            'C138 H134'
_chemical_formula_weight         1792.44
_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             2022-08-05
_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                86.013(3)
_cell_angle_beta                 86.561(3)
_cell_angle_gamma                73.993(3)
_cell_formula_units_Z            2
_cell_length_a                   15.4947(8)
_cell_length_b                   17.9161(9)
_cell_length_c                   19.1436(10)
_cell_measurement_reflns_used    9602
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.72
_cell_measurement_theta_min      3.84
_cell_volume                     5091.3(5)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0531
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            83077
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.857
_diffrn_reflns_theta_max         66.857
_diffrn_reflns_theta_min         2.570
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1212 before and 0.0799 after correction.
The Ratio of minimum to maximum transmission is 0.7990.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic dark violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             1924
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.00050(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1300
_refine_ls_number_reflns         17695
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0585
_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/[\s^2^(Fo^2^)+(0.0701P)^2^+3.8495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15600
_reflns_number_total             17695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02285d10.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1569350--1569353.cif.'
_cod_database_code               1569351
_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
 C03O-C03R \\sim C2-C3
 with sigma of 0.02
 C03O-C03S \\sim C2-C4
 with sigma of 0.02
 C03R-C03U \\sim C3-C03V
 with sigma of 0.04
 C03P-C03R \\sim C5-C3
 with sigma of 0.02
 C03P-C03U \\sim C5-C03V
 with sigma of 0.02
 C03P-C03T \\sim C5-C6
 with sigma of 0.04
 C03Q-C03R \\sim C1-C3
 with sigma of 0.02
 C03P-C03Q \\sim C5-C1
 with sigma of 0.04
 C03S-C03T \\sim C4-C6
 with sigma of 0.02
 C03R-C03S \\sim C3-C4
 with sigma of 0.04
 C03T-C03U \\sim C6-C03V
 with sigma of 0.02
 C03S-C03U \\sim C4-C03V
 with sigma of 0.04
 C03O-C03P \\sim C2-C5
 with sigma of 0.04
 C03O-C03Q \\sim C2-C1
 with sigma of 0.04
 C03O-C03T \\sim C2-C6
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C03V) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6) \\sim Ueq: with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C03T) \\sim Ueq, Uanis(C03Q) \\sim Ueq, Uanis(C03R) \\sim Ueq,
Uanis(C03O) \\sim Ueq, Uanis(C03P) \\sim Ueq, Uanis(C03S) \\sim Ueq,
Uanis(C03U) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C03Q(0.5) H14(0.5) HS(0.5) HT(0.5) C03R(0.5) C03O(0.5) H15(0.5)
 C03S(0.5) H16(0.5) C03T(0.5) H17(0.5) C03U(0.5) H18(0.5) C03P(0.5) H19(0.5)
 C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C5(0.5) H5A(0.5) C03V(0.5) H20(0.5) C6(0.5)
 H6A(0.5) C4(0.5) H4A(0.5) C2(0.5) H2A(0.5) C3(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C01G(H01A,H01C), C01N(H01D,H01E), C01Q(H01F,H01G), C01Z(H01H,
 H01J), C021(H02A,H02B), C023(H02C,H02D), C024(H02E,H02F), C028(H02G,H02H),
 C02D(H02J,H02K), C02F(H02O,H02P), C02H(H02R,H02S), C02M(H02Y,H), C02O(H02,HC),
 C02P(H1,HD), C02R(H3,HE), C02Y(H8,HN), C031(H03A,H03B)
5.b Aromatic/amide H refined with riding coordinates:
 C003(H003), C00D(H00D), C00E(H00E), C00H(H00H), C00N(H00N), C00R(H00R),
 C00T(H00T), C014(H014), C017(H017), C01B(H01B), C01I(H01I), C01K(H01K),
 C01L(H01L), C01M(H01M), C01P(H01P), C01R(H01R), C01V(H01V), C01X(H01X),
 C01Y(H01Y), C020(H020), C022(H022), C025(H025), C026(H026), C027(H027),
 C029(H029), C02A(H02I), C02G(H02Q), C02I(H02T), C02L(H02X), C02Q(H2), C02X(H9),
  C030(H030), C032(H032), C033(H033), C038(H038), C039(H039), C03A(H03Y),
 C03C(H03R), C03D(H03Z), C03F(H03), C03H(H11), C03I(H03S), C03J(H12),
 C03K(H03T), C03M(H03U), C03O(H15), C03S(H16), C03T(H17), C03U(H18), C03P(H19),
 C5(H5A), C03V(H20), C6(H6A), C4(H4A), C2(H2A)
5.c Fitted hexagon refined as free rotating group:
 C03R(C03O,C03S,C03T,C03U,C03P), C5(C03V,C6,C4,C2,C3)
5.d Idealised Me refined as rotating group:
 C02E(H02L,H02M,H02N), C02J(H02U,H02V,H02W), C02N(H02Z,HA,HB), C02S(H4,HF,HG),
 C02T(H5,HH,HI), C02U(H6,HJ,HK), C02W(H7,HL,HM), C02Z(H10,HO,HP), C034(H03C,
 H03D,H03E), C035(H03F,H03G,H03H), C037(H03I,H03J,H03K), C03E(H03L,H03M,H03N),
 C03G(H03O,H03P,H03Q), C03L(H13,HQ,HR), C03N(H03V,H03W,H03X), C03Q(H14,HS,HT),
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              41820
_shelx_hkl_checksum              12885
_olex2_submission_special_instructions 'No special instructions were received'