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_7130561
_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_formula_moiety         'C48 H34 O2'
_chemical_formula_sum            'C48 H34 O2'
_chemical_formula_weight         642.75
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2022-06-07
_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                69.825(2)
_cell_angle_beta                 80.955(2)
_cell_angle_gamma                81.076(2)
_cell_formula_units_Z            3
_cell_length_a                   10.2979(5)
_cell_length_b                   17.4037(10)
_cell_length_c                   17.5627(9)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.389
_cell_volume                     2900.4(3)
_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 0.983
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33052
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_min         2.014
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_description       block
_exptl_crystal_F_000             1014
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
TITL 06072_0m_a.res in P1
CELL   10.2979   17.4037   17.5627     69.82     80.96     81.08
SPGR P1
C101 0.707 0.279 0.409 !       4.34 eA-3
C102 0.523 0.424 0.424 !       4.14 eA-3
C103 0.695 0.197 0.474 !       3.95 eA-3
C104 0.869 0.250 0.272 !       3.88 eA-3
C105 0.790 0.161 0.466 !       3.54 eA-3
C106 0.593 0.220 0.527 !       3.40 eA-3
C107 0.803 0.139 0.493 !       3.39 eA-3
C108 0.931 0.328 0.201 !       3.37 eA-3
C109 0.473 0.376 0.338 !       3.11 eA-3
C110 0.937 0.327 0.328 !       2.85 eA-3
C111 0.456 0.472 0.379 !       2.69 eA-3
C112 0.850 0.408 0.187 !       2.63 eA-3
C113 0.066 0.330 0.238 !       2.12 eA-3
C114 0.309 0.475 0.326 !       1.99 eA-3
C115 0.404 0.438 0.339 !       1.88 eA-3
C116 0.971 0.314 0.269 !       1.87 eA-3
Q117 0.339 0.510 0.403 !       1.41 eA-3
C118 0.322 0.454 0.390 !       1.32 eA-3
Q119 0.487 0.517 0.406 !       1.24 eA-3
Q120 0.920 0.686 0.513 !       1.23 eA-3
C121 0.471 0.503 0.291 !       1.21 eA-3
C122 0.621 0.350 0.374 !       1.12 eA-3
C123 0.782 0.162 0.405 !       1.12 eA-3
C124 0.551 0.206 0.483 !       1.07 eA-3
Q125 0.774 0.391 0.453 !       1.06 eA-3
Q126 0.541 0.513 0.278 !       1.05 eA-3
C127 0.880 0.475 0.170 !       1.04 eA-3
Q128 0.263 0.264 0.198 !       1.03 eA-3
Q129 0.810 0.499 0.474 !       1.02 eA-3
Q130 1.007 0.627 0.495 !       1.01 eA-3
Q131 0.260 0.560 0.700 !       1.01 eA-3
C132 0.453 0.314 0.408 !       0.97 eA-3
C133 0.160 0.410 0.253 !       0.94 eA-3
Q134 0.837 0.404 0.506 !       0.92 eA-3
Q135 0.746 0.067 0.750 !       0.90 eA-3
Q136 0.693 0.346 0.208 !       0.89 eA-3
C137 0.616 0.186 0.612 !       0.89 eA-3
Q138 0.780 0.160 0.330 !       0.88 eA-3
Q139 1.012 0.895 0.909 !       0.88 eA-3
Q140 0.668 0.672 0.249 !       0.88 eA-3
C141 0.466 0.371 0.514 !       0.88 eA-3
C142 0.641 0.296 0.542 !       0.87 eA-3
Q143 0.843 0.215 0.516 !       0.84 eA-3
Q144 0.293 0.432 0.471 !       0.84 eA-3
Q145 0.235 0.376 0.264 !       0.83 eA-3
Q146 0.531 0.583 0.250 !       0.83 eA-3
C147 0.865 0.368 0.141 !       0.83 eA-3
Q148 0.243 0.781 0.777 !       0.83 eA-3
Q149 0.473 0.472 0.238 !       0.82 eA-3
Q150 0.742 0.535 0.161 !       0.80 eA-3
Q151 0.246 0.563 0.375 !       0.79 eA-3
Q152 0.034 0.406 0.296 !       0.78 eA-3
Q153 0.759 0.666 0.441 !       0.78 eA-3
Q154 0.821 0.138 0.699 !       0.78 eA-3
C155 0.724 0.269 0.531 !       0.77 eA-3
Q156 0.945 0.683 0.311 !       0.77 eA-3
Q157 0.092 0.548 0.655 !       0.77 eA-3
Q158 0.749 0.198 0.314 !       0.76 eA-3
Q159 0.129 0.313 0.343 !       0.76 eA-3
Q160 0.044 0.559 0.280 !       0.76 eA-3
Q161 0.295 0.609 0.608 !       0.76 eA-3
Q162 0.848 0.096 0.343 !       0.75 eA-3
Q163 0.406 0.635 0.689 !       0.75 eA-3
Q164 0.983 0.895 0.825 !       0.74 eA-3
Q165 0.273 0.294 0.372 !       0.74 eA-3
Q166 0.820 0.334 0.424 !       0.74 eA-3
Q167 0.072 0.155 0.199 !       0.74 eA-3
Q168 0.162 0.518 0.310 !       0.73 eA-3
C169 0.802 0.248 0.469 !       0.73 eA-3
Q170 0.303 0.299 0.324 !       0.73 eA-3
Q171 0.013 0.287 0.408 !       0.73 eA-3
Q172 0.061 0.420 0.312 !       0.73 eA-3
Q173 0.148 0.723 0.830 !       0.73 eA-3
Q174 0.097 0.594 0.577 !       0.72 eA-3
Q175 0.944 0.919 0.124 !       0.72 eA-3
Q176 0.876 0.438 0.041 !       0.72 eA-3
Q177 0.872 0.296 0.470 !       0.71 eA-3
Q178 0.101 0.364 0.333 !       0.71 eA-3
Q179 0.104 0.844 0.956 !       0.70 eA-3
Q180 0.835 0.568 0.065 !       0.69 eA-3
Q181 0.969 0.129 0.683 !       0.69 eA-3
C182 0.292 0.536 0.282 !       0.69 eA-3
Q183 0.654 0.464 0.137 !       0.69 eA-3
Q184 0.275 0.783 0.703 !       0.69 eA-3
Q185 0.903 0.332 0.408 !       0.69 eA-3
Q186 0.735 0.404 0.137 !       0.68 eA-3
Q187 0.418 0.576 0.374 !       0.67 eA-3
C188 0.496 0.303 0.426 !       0.67 eA-3
C189 0.704 0.137 0.532 !       0.67 eA-3
Q190 0.546 0.748 0.452 !       0.67 eA-3
Q191 0.903 0.613 0.111 !       0.66 eA-3
Q192 0.520 0.846 0.920 !       0.66 eA-3
Q193 0.589 0.768 0.955 !       0.65 eA-3
C194 0.046 0.389 0.141 !       0.65 eA-3
C195 0.213 0.432 0.279 !       0.65 eA-3
Q196 0.228 0.361 0.231 !       0.65 eA-3
Q197 0.466 0.644 0.692 !       0.64 eA-3
Q198 0.997 0.644 0.842 !       0.64 eA-3
Q199 1.009 0.497 0.114 !       0.64 eA-3
;
_refine_diff_density_max         1.204
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 4401 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.270
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1340
_refine_ls_number_reflns         19422
_refine_ls_number_restraints     2331
_refine_ls_restrained_S_all      1.268
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.1096
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3006
_refine_ls_wR_factor_ref         0.3364
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.681
_reflns_Friedel_fraction_max     0.634
_reflns_number_gt                13875
_reflns_number_total             19422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04139a2.cif
_cod_data_source_block           06072_0m_sq_sq
_cod_database_code               7130561
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.830(4)
 0.170(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
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
 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
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C28) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C009) \\sim Ueq, Uanis(C29) \\sim Ueq,
Uanis(C00C) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C00F)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C00H) \\sim Ueq, Uanis(C26) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C00L) \\sim Ueq, Uanis(C00M)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C41) \\sim Ueq,
Uanis(C00Q) \\sim Ueq, Uanis(C00R) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C00U) \\sim Ueq, Uanis(C00V) \\sim Ueq, Uanis(C00W) \\sim Ueq,
Uanis(C00X) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C012) \\sim Ueq, Uanis(C013) \\sim Ueq,
Uanis(C44) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C37) \\sim Ueq,
Uanis(C01B) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C01E)
\\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C01G) \\sim Ueq, Uanis(C33) \\sim Ueq,
Uanis(C01J) \\sim Ueq, Uanis(C01K) \\sim Ueq, Uanis(C01L) \\sim Ueq,
Uanis(C01M) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C01O) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C01R) \\sim Ueq, Uanis(C01S) \\sim Ueq,
Uanis(C46) \\sim Ueq, Uanis(C01U) \\sim Ueq, Uanis(C01V) \\sim Ueq, Uanis(C01W)
\\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C01Y) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C020) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C022) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C024) \\sim Ueq, Uanis(C025) \\sim Ueq, Uanis(C026) \\sim Ueq,
Uanis(C027) \\sim Ueq, Uanis(C028) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C39)
\\sim Ueq, Uanis(C02C) \\sim Ueq, Uanis(C02D) \\sim Ueq, Uanis(C02E) \\sim Ueq,
Uanis(C17) \\sim Ueq, Uanis(C02G) \\sim Ueq, Uanis(C02H) \\sim Ueq, Uanis(C02I)
\\sim Ueq, Uanis(C02J) \\sim Ueq, Uanis(C02K) \\sim Ueq, Uanis(C02L) \\sim Ueq,
Uanis(C30) \\sim Ueq, Uanis(C02N) \\sim Ueq, Uanis(C02O) \\sim Ueq, Uanis(C02P)
\\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C02S) \\sim Ueq, Uanis(C02T) \\sim Ueq,
Uanis(C02U) \\sim Ueq, Uanis(C02V) \\sim Ueq, Uanis(C02W) \\sim Ueq,
Uanis(C02X) \\sim Ueq, Uanis(C02Y) \\sim Ueq, Uanis(C02Z) \\sim Ueq,
Uanis(C030) \\sim Ueq, Uanis(C031) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C033)
\\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C035) \\sim Ueq, Uanis(C036) \\sim Ueq,
Uanis(C037) \\sim Ueq, Uanis(C038) \\sim Ueq, Uanis(C039) \\sim Ueq,
Uanis(C03A) \\sim Ueq, Uanis(C03B) \\sim Ueq, Uanis(C03C) \\sim Ueq,
Uanis(C03D) \\sim Ueq, Uanis(C03F) \\sim Ueq, Uanis(C03G) \\sim Ueq,
Uanis(C03H) \\sim Ueq, Uanis(C03I) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C03K)
\\sim Ueq, Uanis(C03L) \\sim Ueq, Uanis(C03M) \\sim Ueq, Uanis(C03N) \\sim Ueq,
Uanis(C03O) \\sim Ueq, Uanis(C03P) \\sim Ueq, Uanis(C03Q) \\sim Ueq,
Uanis(C03R) \\sim Ueq, Uanis(C03S) \\sim Ueq, Uanis(C03T) \\sim Ueq,
Uanis(C03U) \\sim Ueq, Uanis(C03V) \\sim Ueq, Uanis(C03W) \\sim Ueq,
Uanis(C03X) \\sim Ueq, Uanis(C03Y) \\sim Ueq, Uanis(C03Z) \\sim Ueq,
Uanis(C040) \\sim Ueq, Uanis(C041) \\sim Ueq, Uanis(C043) \\sim Ueq,
Uanis(C048) \\sim Ueq, Uanis(C049) \\sim Ueq, Uanis(C04B) \\sim Ueq,
Uanis(C04D) \\sim Ueq, Uanis(C04E) \\sim Ueq, Uanis(C04H) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
5.a Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C21(H21A,H21B), C02Z(H02A,H02B), C03A(H03A,H03B), C03W(H03F,
 H03H), C041(H04A,H04B)
5.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C34(H34), C23(H23), C00H(H00H), C26(H26), C8(H8), C24(H24),
 C25(H25), C00Q(H00Q), C00R(H00R), C00U(H00U), C00W(H00W), C00X(H00X), C2(H2),
 C012(H012), C013(H013), C44(H44), C3(H3), C13(H13), C40(H40), C37(H37),
 C48(H48), C5(H5), C33(H33), C01K(H01K), C01M(H01M), C38(H38), C01O(H01O),
 C14(H14), C19(H19), C01S(H01S), C46(H46), C01U(H01U), C45(H45), C01Y(H01Y),
 C15(H15), C16(H16), C022(H022), C7(H7), C024(H024), C026(H026), C028(H028),
 C18(H18), C39(H39), C02C(H02C), C02E(H02E), C02G(H02G), C02H(H02H), C02I(H02I),
  C02K(H02K), C02L(H02L), C30(H30), C02O(H02O), C47(H47), C02S(H02S),
 C02T(H02T), C02V(H02V), C02X(H02X), C02Y(H02Y), C031(H031), C31(H31),
 C033(H033), C32(H32), C036(H036), C038(H038), C039(H039), C03B(H03C),
 C03C(H03E), C03D(H03D), C03G(H03G), C03I(H03I), C6(H6), C03K(H03K), C03L(H03L),
  C03N(H03N), C03P(H03P), C03Q(H03Q), C03T(H03T), C03V(H03V), C03X(H03X),
 C03U(H03U), C03S(H03S), C03Z(H03Z), C040(H040), C043(H043), C049(H049),
 C04B(H04C), C04D(H04D), C04E(H04E), C04H(H04H)
5.c Fitted hexagon refined as free rotating group:
 C03Y(C035,C037,C03O,C03U,C03S)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'