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_1569353
_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         'C92 H62, 1.998(C7 H8)'
_chemical_formula_sum            'C105.99 H77.99'
_chemical_formula_weight         1351.48
_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
_audit_creation_date             2023-02-05
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2023-03-14 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                72.5110(10)
_cell_angle_beta                 77.9020(10)
_cell_angle_gamma                82.932(2)
_cell_formula_units_Z            2
_cell_length_a                   12.6773(3)
_cell_length_b                   17.7433(4)
_cell_length_c                   18.0024(4)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.14
_cell_measurement_theta_min      2.62
_cell_volume                     3768.61(15)
_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  'SHELXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0783
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            80370
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         2.617
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1120 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.8731.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             1428
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1392
_refine_ls_number_reflns         13163
_refine_ls_number_restraints     1850
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0766
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+5.9008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9672
_reflns_number_total             13163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02285d10.cif
_cod_data_source_block           szt20230105
_cod_depositor_comments
'Adding full bibliography for 1569350--1569353.cif.'
_cod_database_code               1569353
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.914
_olex2_refinement_description
;
1. Shared sites
{C5, C5A}
{C89, C89A}
2. Restrained distances
 C93-C94 = C94-C95 = C95-C96 = C96-C97 = C97-C98 = C98-C93
 1.395 with sigma of 0.01
 C93B-C94B = C94B-C95B = C95B-C96B = C96B-C97B = C97B-C98B = C98B-C93B
 1.395 with sigma of 0.01
 C93-C95 \\sim C94-C96 \\sim C95-C97 \\sim C96-C98 \\sim C97-C93
 with sigma of 0.01
3. Restrained planarity
 C93B, C94B, C95B, C96B, C97B, C98B, C99B
 with sigma of 0.001
 C00B, C01B, C02B, C03B, C04B, C05B, C06B
 with sigma of 0.001
4. Rigid bond restraints
 C1, C2, C3, C5, C6, C7, C8, C9, C1A, C2A, C3A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C56, C57, C58, C59, C60, C56A, C57A, C58A, C59A, C60A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C85, C86, C87, C88, C89, C90, C91, C92, C85A, C86A, C87A, C88A, C89A, C90A,
 C91A, C92A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C93, C94, C95, C96, C97, C98, C99, C93A, C94A, C95A, C96A, C97A, C98A, C99A,
 C93B, C94B, C95B, C96B, C97B, C98B, C99B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C100, C101, C102, C103, C104, C105, C106, C00A, C01A, C02A, C03A, C04A, C05A,
 C06A, C00B, C01B, C02B, C03B, C04B, C05B, C06B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C1A
\\sim C2A \\sim C3A \\sim C5A \\sim C6A \\sim C7A \\sim C8A \\sim C9A: within
2A with sigma of 0.002 and sigma for terminal atoms of 0.003 within 2A
C56 \\sim C57 \\sim C58 \\sim C59 \\sim C60 \\sim C56A \\sim C57A \\sim C58A
\\sim C59A \\sim C60A: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.003 within 2A
C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89 \\sim C90 \\sim C91 \\sim C92 \\sim
C85A \\sim C86A \\sim C87A \\sim C88A \\sim C89A \\sim C90A \\sim C91A \\sim
C92A: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.003
within 2A
C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97 \\sim C98 \\sim C99 \\sim C93A
\\sim C94A \\sim C95A \\sim C96A \\sim C97A \\sim C98A \\sim C99A \\sim C93B
\\sim C94B \\sim C95B \\sim C96B \\sim C97B \\sim C98B \\sim C99B: within 2A
with sigma of 0.002 and sigma for terminal atoms of 0.003 within 2A
C100 \\sim C101 \\sim C102 \\sim C103 \\sim C104 \\sim C105 \\sim C106 \\sim
C00A \\sim C01A \\sim C02A \\sim C03A \\sim C04A \\sim C05A \\sim C06A \\sim
C00B \\sim C01B \\sim C02B \\sim C03B \\sim C04B \\sim C05B \\sim C06B: within
2A with sigma of 0.002 and sigma for terminal atoms of 0.003 within 2A
Uanis(C5) = Uanis(C5A)
Uanis(C89) = Uanis(C89A)
6. Same fragment restrains
{C1A, C2A, C3A, C5A, C6A, C7A, C8A, C9A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C1, C2, C3, C5, C6, C7, C8, C9}
{C56A, C57A, C58A, C59A, C60A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C56, C57, C58, C59, C60}
{C85A, C86A, C87A, C88A, C89A, C90A, C91A, C92A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C85, C86, C87, C88, C89, C90, C91, C92}
{C93A, C94A, C95A, C96A, C97A, C98A, C99A} sigma for 1-2: 0.02, 1-3: 0.04
{C93B, C94B, C95B, C96B, C97B, C98B, C99B} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C93, C94, C95, C96, C97, C98, C99}
{C00A, C01A, C02A, C03A, C04A, C05A, C06A} sigma for 1-2: 0.02, 1-3: 0.04
{C00B, C01B, C02B, C03B, C04B, C05B, C06B} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C100, C101, C102, C103, C104, C105, C106}
7. Others
 1*[Sof(C93)+Sof(C94)+Sof(H63)+Sof(C95)+Sof(H64)+Sof(C96)+Sof(H65)+Sof(C97)+
 Sof(H66)+Sof(C98)+Sof(H67)+Sof(C99)+Sof(H68)+Sof(H69)+Sof(H70)]+1*[Sof(C93A)+
 Sof(C94A)+Sof(H71)+Sof(C95A)+Sof(H72)+Sof(C96A)+Sof(H73)+Sof(C97A)+Sof(H74)+
 Sof(C98A)+Sof(H75)+Sof(C99A)+Sof(H76)+Sof(H77)+Sof(H78)]+1*[Sof(C93B)+
 Sof(C94B)+Sof(H94B)+Sof(C95B)+Sof(H95B)+Sof(C96B)+Sof(H96B)+Sof(C97B)+
 Sof(H97B)+Sof(C98B)+Sof(H98B)+Sof(C99B)+Sof(H99A)+Sof(H99B)+Sof(H99C)]=1 with
 esd of 0.001
 1*[Sof(C100)+Sof(C101)+Sof(H79)+Sof(C102)+Sof(H80)+Sof(C103)+Sof(H81)+
 Sof(C104)+Sof(H82)+Sof(C105)+Sof(H83)+Sof(C106)+Sof(H84)+Sof(H85)+Sof(H86)]+1*
 [Sof(C00A)+Sof(C01A)+Sof(H87)+Sof(C02A)+Sof(H88)+Sof(C03A)+Sof(H89)+Sof(C04A)+
 Sof(H90)+Sof(C05A)+Sof(H91)+Sof(C06A)+Sof(H92)+Sof(H93)+Sof(H94)]+1*[Sof(C00B)+
 Sof(C01B)+Sof(H95)+Sof(C02B)+Sof(H96)+Sof(C03B)+Sof(H97)+Sof(C04B)+Sof(H98)+
 Sof(C05B)+Sof(H99)+Sof(C06B)+Sof(H100)+Sof(H101)+Sof(H102)]=1 with esd of 0.001
 Sof(C1A)=Sof(C2A)=Sof(HK)=Sof(C3A)=Sof(C5A)=Sof(C6A)=Sof(HL)=Sof(C7A)=Sof(HM)=
 Sof(HN)=Sof(HO)=Sof(C8A)=Sof(HP)=Sof(HQ)=Sof(HR)=Sof(C9A)=Sof(HS)=Sof(HT)=
 Sof(HU)=1-FVAR(1)
 Sof(C1)=Sof(C2)=Sof(H)=Sof(C3)=Sof(C5)=Sof(C6)=Sof(HA)=Sof(C7)=Sof(HB)=
 Sof(HC)=Sof(HD)=Sof(C8)=Sof(HE)=Sof(HF)=Sof(HG)=Sof(C9)=Sof(HH)=Sof(HI)=
 Sof(HJ)=FVAR(1)
 Sof(C85A)=Sof(C86A)=Sof(H52)=Sof(C87A)=Sof(C88A)=Sof(H53)=Sof(C89A)=Sof(C90A)=
 Sof(H54)=Sof(H55)=Sof(H56)=Sof(C91A)=Sof(H57)=Sof(H58)=Sof(H59)=Sof(C92A)=
 Sof(H60)=Sof(H61)=Sof(H62)=1-FVAR(2)
 Sof(C85)=Sof(C86)=Sof(H41)=Sof(C87)=Sof(C88)=Sof(H42)=Sof(C89)=Sof(C90)=
 Sof(H43)=Sof(H44)=Sof(H45)=Sof(C91)=Sof(H46)=Sof(H47)=Sof(H48)=Sof(C92)=
 Sof(H49)=Sof(H50)=Sof(H51)=FVAR(2)
 Sof(C56A)=Sof(H24)=Sof(C57A)=Sof(H25)=Sof(C58A)=Sof(H26)=Sof(C59A)=Sof(H27)=
 Sof(C60A)=Sof(H28)=1-FVAR(3)
 Sof(C56)=Sof(H19)=Sof(C57)=Sof(H20)=Sof(C58)=Sof(H21)=Sof(C59)=Sof(H22)=
 Sof(C60)=Sof(H23)=FVAR(3)
 Sof(C93)=Sof(C94)=Sof(H63)=Sof(C95)=Sof(H64)=Sof(C96)=Sof(H65)=Sof(C97)=
 Sof(H66)=Sof(C98)=Sof(H67)=Sof(C99)=Sof(H68)=Sof(H69)=Sof(H70)=FVAR(4)
 Sof(C93A)=Sof(C94A)=Sof(H71)=Sof(C95A)=Sof(H72)=Sof(C96A)=Sof(H73)=Sof(C97A)=
 Sof(H74)=Sof(C98A)=Sof(H75)=Sof(C99A)=Sof(H76)=Sof(H77)=Sof(H78)=FVAR(5)
 Sof(C93B)=Sof(C94B)=Sof(H94B)=Sof(C95B)=Sof(H95B)=Sof(C96B)=Sof(H96B)=
 Sof(C97B)=Sof(H97B)=Sof(C98B)=Sof(H98B)=Sof(C99B)=Sof(H99A)=Sof(H99B)=
 Sof(H99C)=FVAR(6)
 Sof(C100)=Sof(C101)=Sof(H79)=Sof(C102)=Sof(H80)=Sof(C103)=Sof(H81)=Sof(C104)=
 Sof(H82)=Sof(C105)=Sof(H83)=Sof(C106)=Sof(H84)=Sof(H85)=Sof(H86)=FVAR(7)
 Sof(C00A)=Sof(C01A)=Sof(H87)=Sof(C02A)=Sof(H88)=Sof(C03A)=Sof(H89)=Sof(C04A)=
 Sof(H90)=Sof(C05A)=Sof(H91)=Sof(C06A)=Sof(H92)=Sof(H93)=Sof(H94)=FVAR(8)
 Sof(C00B)=Sof(C01B)=Sof(H95)=Sof(C02B)=Sof(H96)=Sof(C03B)=Sof(H97)=Sof(C04B)=
 Sof(H98)=Sof(C05B)=Sof(H99)=Sof(C06B)=Sof(H100)=Sof(H101)=Sof(H102)=FVAR(9)
8.a Me refined with riding coordinates:
 C06B(H100,H101,H102)
8.b Aromatic/amide H refined with riding coordinates:
 C2(H), C6(HA), C2A(HK), C6A(HL), C12(HV), C13(HW), C14(HX), C15(HY), C20(HZ),
 C21(H1), C22(H2), C26(H3), C27(H4), C28(H5), C29(H6), C30(H7), C35(H8),
 C36(H9), C37(H10), C38(H11), C39(H12), C41(H13), C42(H14), C43(H15), C48(H16),
 C49(H17), C50(H18), C56(H19), C57(H20), C58(H21), C59(H22), C60(H23),
 C56A(H24), C57A(H25), C58A(H26), C59A(H27), C60A(H28), C65(H29), C66(H30),
 C67(H31), C68(H32), C69(H33), C71(H34), C72(H35), C73(H36), C77(H37), C78(H38),
  C79(H39), C80(H40), C86(H41), C88(H42), C86A(H52), C88A(H53), C94(H63),
 C95(H64), C96(H65), C97(H66), C98(H67), C94A(H71), C95A(H72), C96A(H73),
 C97A(H74), C98A(H75), C94B(H94B), C95B(H95B), C96B(H96B), C97B(H97B),
 C98B(H98B), C101(H79), C102(H80), C103(H81), C104(H82), C105(H83), C01A(H87),
 C02A(H88), C03A(H89), C04A(H90), C05A(H91), C01B(H95), C02B(H96), C03B(H97),
 C04B(H98), C05B(H99)
8.c Fitted hexagon refined as free rotating group:
 C55(C56,C57,C58,C59,C60)
8.d Idealised Me refined as rotating group:
 C7(HB,HC,HD), C8(HE,HF,HG), C9(HH,HI,HJ), C7A(HM,HN,HO), C8A(HP,HQ,HR),
 C9A(HS,HT,HU), C90(H43,H44,H45), C91(H46,H47,H48), C92(H49,H50,H51), C90A(H54,
 H55,H56), C91A(H57,H58,H59), C92A(H60,H61,H62), C99(H68,H69,H70), C99A(H76,H77,
 H78), C99B(H99A,H99B,H99C), C106(H84,H85,H86), C06A(H92,H93,H94)
;
_olex2_submission_special_instructions 'No special instructions were received'