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_7133317
_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_absolute_configuration rm
_chemical_formula_moiety         'C H2 Cl2, C52 H26 N2 O4'
_chemical_formula_sum            'C53 H28 Cl2 N2 O4'
_chemical_formula_weight         827.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 92.329(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1505(5)
_cell_length_b                   11.3913(8)
_cell_length_c                   20.8223(13)
_cell_measurement_reflns_used    3822
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      2.65
_cell_volume                     1931.6(2)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_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  0.0753
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14940
_diffrn_reflns_point_group_measured_fraction_full 0.869
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.415
_diffrn_reflns_theta_min         1.958
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0820 after correction.
The Ratio of minimum to maximum transmission is 0.7318.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         6770
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+0.6930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.737
_reflns_Friedel_fraction_max     0.706
_reflns_number_gt                4986
_reflns_number_total             6770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02747g2.cif
_cod_data_source_block           tm1_0m
_cod_depositor_comments
'Adding full bibliography for 7133317--7133318.cif.'
_cod_database_code               7133317
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C26(H26), C19(H19), C52(H52), C43(H43), C49(H49), C2(H2),
 C13(H13), C16(H16), C14(H14), C39(H39), C46(H46), C7(H7), C18(H18), C27(H27),
 C15(H15), C38(H38), C50(H50), C37(H37), C44(H44), C28(H28), C3(H3), C51(H51),
 C45(H45), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'