Chiral cyclic architectonics with tetraphenylethylenes: conformation immobilization, optical resolution and circularly polarized luminescence
Meng, Qi; Cui, Liwen; Liao, Qi; Xu, Jian; Wang, Yuxiang; Chemical Communications  (2022) –; doi:10.1039/D2CC04139A

data_7130560
_publ_section_title
;
 Chiral cyclic architectonics with tetraphenylethylenes: conformation
 immobilization, optical resolution and circularly polarized luminescence
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04139A
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C48 H34 O2'
_chemical_formula_sum            'C48 H34 O2'
_chemical_formula_weight         642.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-29 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.691(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.682(2)
_cell_length_b                   11.1603(9)
_cell_length_c                   27.232(3)
_cell_measurement_reflns_used    5284
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.407
_cell_measurement_theta_min      2.364
_cell_volume                     8042.3(12)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_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  0.0646
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34565
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         1.980
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0755 before and 0.0636 after correction. The Ratio of minimum to maximum transmission is 0.9011. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_description       block
_exptl_crystal_F_000             2704
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
TITL 1_0m_a.res in C2
CELL   28.6820   11.1603   27.2320     90.00    112.69     90.00
SPGR C2
C101 0.973 0.456 0.323 !      13.28 eA-3
C102 0.062 0.323 0.374 !       8.02 eA-3
C103 0.952 0.432 0.452 !       6.86 eA-3
C104 0.978 0.083 0.540 !       5.93 eA-3
C105 0.234 0.341 0.689 !       5.73 eA-3
C106 0.820 0.348 0.310 !       5.53 eA-3
C107 0.104 0.191 0.620 !       5.40 eA-3
C108 0.463 0.058 0.031 !       5.36 eA-3
C109 0.797 0.341 0.317 !       5.23 eA-3
C110 0.475 0.485 0.529 !       5.06 eA-3
C111 0.880 0.175 0.348 !       4.68 eA-3
C112 0.453 0.109-0.001 !       3.94 eA-3
C113 0.182 0.213 0.658 !       3.12 eA-3
C114 0.854 0.307 0.321 !       2.82 eA-3
C115 0.993 0.303 0.343 !       2.59 eA-3
C116 0.511 0.163 0.994 !       2.54 eA-3
C117 0.970 0.434 0.498 !       2.07 eA-3
C118 0.965 0.411 0.623 !       2.07 eA-3
C119 0.985 0.437 0.524 !       1.89 eA-3
C120 1.000 0.106 0.495 !       1.81 eA-3
C121 0.025 0.355 0.572 !       1.49 eA-3
C122 0.943 0.031 0.475 !       1.42 eA-3
C123 1.000 0.492 0.523 !       1.36 eA-3
C124 0.997 0.430 0.631 !       1.28 eA-3
C125 1.000 0.435 0.501 !       1.25 eA-3
Q126 0.026 0.155 0.350 !       1.19 eA-3
Q127 1.002 0.354 0.302 !       1.13 eA-3
C128 0.962 0.331 0.595 !       1.12 eA-3
C129 0.907 0.273 0.611 !       1.11 eA-3
C130 1.003 0.356 0.415 !       1.09 eA-3
C131 0.518 0.497 0.516 !       1.06 eA-3
Q132 0.069 0.399 0.337 !       1.05 eA-3
C133 0.043 0.318 0.492 !       1.05 eA-3
Q134 0.937 0.284 0.494 !       1.04 eA-3
Q135 0.572 0.205 0.053 !       1.04 eA-3
C136 0.961 0.401 0.537 !       1.04 eA-3
Q137 0.587 0.022 0.667 !       1.03 eA-3
C138 0.498 0.027 0.038 !       1.02 eA-3
Q139 0.977 0.326 0.712 !       1.02 eA-3
C140 0.044 0.175 0.481 !       1.01 eA-3
C141 0.971 0.143 0.452 !       1.00 eA-3
Q142 0.500 0.048 0.458 !       0.99 eA-3
C143 0.501 0.030 0.001 !       0.97 eA-3
C144 0.030 0.286 0.568 !       0.97 eA-3
Q145 0.546 0.017 0.500 !       0.95 eA-3
Q146 0.835 0.046 0.321 !       0.94 eA-3
C147 0.053 0.198 0.594 !       0.93 eA-3
Q148 0.169 0.182 0.603 !       0.93 eA-3
Q149 0.404 0.024 0.895 !       0.93 eA-3
Q150 0.515 0.147 0.055 !       0.92 eA-3
Q151 0.988 0.191 0.298 !       0.92 eA-3
Q152 0.069 0.474 0.975 !       0.91 eA-3
C153 0.226 0.431 0.719 !       0.91 eA-3
C154 0.958 0.082 0.460 !       0.90 eA-3
C155 0.977 0.248 0.524 !       0.89 eA-3
C156 0.032 0.422 0.411 !       0.89 eA-3
C157 0.027 0.151 0.521 !       0.89 eA-3
Q158 0.970 0.282 0.288 !       0.88 eA-3
Q159 0.571 0.131 0.570 !       0.88 eA-3
Q160 0.948 0.252 0.533 !       0.88 eA-3
Q161 0.048 0.077 0.623 !       0.87 eA-3
Q162 0.234 0.110 0.679 !       0.86 eA-3
Q163 0.127 0.314 0.819 !       0.85 eA-3
C164 0.035 0.266 0.437 !       0.85 eA-3
Q165 0.823 0.359 0.373 !       0.85 eA-3
C166 0.088 0.296 0.610 !       0.84 eA-3
Q167 0.360 0.343 0.375 !       0.83 eA-3
Q168 0.296 0.155 0.125 !       0.83 eA-3
Q169 0.016 0.052 0.408 !       0.82 eA-3
Q170 0.515 0.079 0.596 !       0.82 eA-3
C171 0.015 0.032 0.555 !       0.81 eA-3
Q172 0.155 0.454 0.608 !       0.81 eA-3
Q173 0.224 0.172 0.704 !       0.79 eA-3
C174 1.000 0.316 0.445 !       0.78 eA-3
Q175 0.221 0.441 0.233 !       0.78 eA-3
C176 0.124 0.362 0.627 !       0.78 eA-3
C177 0.967 0.011 0.462 !       0.77 eA-3
Q178 0.548 0.108 0.632 !       0.77 eA-3
Q179 0.854 0.360 0.263 !       0.77 eA-3
Q180 0.572 0.153 0.610 !       0.76 eA-3
Q181 0.478 0.183 0.499 !       0.75 eA-3
Q182 0.674 0.150 0.030 !       0.75 eA-3
C183 0.999 0.199 0.499 !       0.75 eA-3
Q184 0.452 0.231 0.431 !       0.74 eA-3
C185 0.063 0.090 0.493 !       0.74 eA-3
Q186 0.042 0.037 0.148 !       0.74 eA-3
Q187 0.430 0.010 0.305 !       0.74 eA-3
Q188 0.411 0.359 0.859 !       0.74 eA-3
C189 0.510 0.043 0.563 !       0.73 eA-3
Q190 0.573 0.056 0.553 !       0.73 eA-3
Q191 0.786 0.454 0.314 !       0.73 eA-3
Q192 0.937 0.391 0.248 !       0.73 eA-3
Q193 0.080 0.186 0.668 !       0.73 eA-3
C194 0.047 0.294 0.656 !       0.72 eA-3
Q195 0.406 0.473 0.399 !       0.71 eA-3
Q196 0.463 0.244 0.334 !       0.70 eA-3
Q197 0.443 0.212 0.462 !       0.70 eA-3
Q198 0.106 0.476 0.735 !       0.70 eA-3
Q199 0.129 0.299 0.421 !       0.70 eA-3
;
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   4.9(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     901
_refine_ls_number_reflns         14895
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+5.0864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1987
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.841
_reflns_Friedel_fraction_max     0.805
_reflns_number_gt                9331
_reflns_number_total             14895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04139a2.cif
_cod_data_source_block           1_0m_sq
_cod_original_cell_volume        8042.2(12)
_cod_database_code               7130560
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.992
_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:
 C21(H21A,H21B), C48(H48A,H48B), C69(H69A,H69B), C93(H93A,H93B)
2.b Aromatic/amide H refined with riding coordinates:
 C50(H50), C90(H90), C46(H46), C19(H19), C51(H51), C78(H78), C56(H56),
 C87(H87), C44(H44), C3(H3), C18(H18), C75(H75), C47(H47), C88(H88), C24(H24),
 C72(H72), C13(H13), C61(H61), C95(H95), C29(H29), C55(H55), C45(H45), C2(H2),
 C89(H89), C83(H83), C66(H66), C94(H94), C86(H86), C67(H67), C74(H74), C97(H97),
  C33(H33), C77(H77), C30(H30), C81(H81), C27(H27), C37(H37), C96(H96), C8(H8),
 C79(H79), C14(H14), C63(H63), C80(H80), C62(H62), C25(H25), C31(H31), C16(H16),
  C54(H54), C15(H15), C26(H26), C32(H32), C41(H41), C38(H38), C73(H73),
 C53(H53), C40(H40), C39(H39), C7(H7), C5(H5), C6(H6)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'