Synthesis and resolution of multi-chiral carbonyl-N embedded hetero[7]helicenes for efficient circularly polarized luminescence.
Wang, Yuxiang; Liao, Qi; Feng, Yabin; Wang, Yiran; Li, Yunzhi; Meng, Qi; Chemical communications (Cambridge, England) 60 (2024) 8292–8295; doi:10.1039/d4cc02747g

data_7133318
_publ_section_title
;
 Synthesis and resolution of multi-chiral carbonyl-N embedded
 hetero[7]helicenes for efficient circularly polarized luminescence.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8292
_journal_page_last               8295
_journal_paper_doi               10.1039/d4cc02747g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C52 H26 N2 O4, 2(C6 H14)'
_chemical_formula_sum            'C64 H54 N2 O4'
_chemical_formula_weight         915.09
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-03
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-12-14 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   13.1642(13)
_cell_length_b                   13.1642(13)
_cell_length_c                   48.250(6)
_cell_measurement_reflns_used    7144
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.090
_cell_measurement_theta_min      2.311
_cell_volume                     7241.3(14)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1303
_diffrn_reflns_av_unetI/netI     0.1497
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            33338
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.190
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.8994.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             2904
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     681
_refine_ls_number_reflns         9239
_refine_ls_number_restraints     888
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.1582
_refine_ls_R_factor_gt           0.0754
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.2032
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                5185
_reflns_number_total             9239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02747g2.cif
_cod_data_source_block           tm2_0m
_cod_depositor_comments
'Adding full bibliography for 7133317--7133318.cif.'
_cod_original_cell_volume        7241.3(17)
_cod_database_code               7133318
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.991
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C67-C65 \\sim C65-C64 \\sim C64-C61 \\sim C61-C60 \\sim C57-C56 \\sim C58-C57
\\sim C55-C56 \\sim C54-C53
 \\sim C55-C54
 with sigma of 0.02
 C65-C69 \\sim C56-C58
 with sigma of 0.02
 C67-C64 \\sim C58-C56
 with sigma of 0.02
 C58-C56 \\sim C60-C64
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C64) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C53)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C64) \\sim Ueq, Uanis(C61) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C67) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C66)
\\sim Ueq, Uanis(C65) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(C54) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Fixed Sof: H60D(0.5) H60E(0.5) H60F(0.5) H60A(0.5) H60B(0.5) H60C(0.5)
 C61(0.5) H61A(0.5) H61B(0.5) C64(0.5) H64A(0.5) H64B(0.5) C65(0.5) H65A(0.5)
 H65B(0.5) C69(0.5) H69A(0.5) H69B(0.5) H69C(0.5) C67(0.5) H67A(0.5) H67B(0.5)
 C62(0.5) H62A(0.5) H62B(0.5) C63(0.5) H63A(0.5) H63B(0.5) C68(0.5) H68A(0.5)
 H68B(0.5) C66(0.5) H66A(0.5) H66B(0.5) C72(0.5) H72A(0.5) H72B(0.5) H72C(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B), C57(H57A,H57B), C54(H54A,H54B), C55(H55A,H55B), C61(H61A,
 H61B), C64(H64A,H64B), C65(H65A,H65B), C67(H67A,H67B), C62(H62A,H62B),
 C63(H63A,H63B), C68(H68A,H68B), C66(H66A,H66B)
6.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C5(H5), C3(H3), C4(H4), C32(H32), C13(H13), C29(H29), C45(H45),
 C51(H51), C42(H42), C31(H31), C50(H50), C23(H23), C39(H39), C11(H11), C46(H46),
  C24(H24), C48(H48), C36(H36), C47(H47), C22(H22), C37(H37), C12(H12),
 C41(H41), C30(H30), C38(H38)
6.c Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C58(H58A,H58B,H58C), C60(H60D,H60E,H60F), C60(H60A,H60B,
 H60C), C69(H69A,H69B,H69C), C72(H72A,H72B,H72C)
;
_olex2_submission_special_instructions 'No special instructions were received'