Aggregation-Induced Emission and Light-Harvesting Function of Tetraphenylethene-Based Tetracationic Dicyclophane.
Li, Yawen; Dong, Yunhong; Cheng, Lin; Qin, Chunyan; Nian, Hao; Zhang, Haiyang; Yu, Yang; Cao, Liping; Journal of the American Chemical Society 141 (2019) 8412–8415; doi:10.1021/jacs.9b02617

data_4128755
_publ_section_title
;
 Aggregation-Induced Emission and Light-Harvesting Function of
 Tetraphenylethene-Based Tetracationic Dicyclophane.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8412
_journal_page_last               8415
_journal_paper_doi               10.1021/jacs.9b02617
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C102 H76 N4, 4(F6 P), C4 H10 O'
_chemical_formula_sum            'C106 H86 F24 N4 O P4'
_chemical_formula_weight         2011.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-04-16
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.619(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.025(2)
_cell_length_b                   14.4111(13)
_cell_length_c                   35.128(3)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.86
_cell_measurement_theta_min      2.35
_cell_volume                     11109.2(17)
_computing_cell_refinement       'SAINT V.8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V.8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Xshell v.6.3.1 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1182
_diffrn_reflns_av_unetI/netI     0.1380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            107155
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.475
_diffrn_reflns_theta_min         2.241
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. Krause, L., 
Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             4136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1474
_refine_ls_number_reflns         20423
_refine_ls_number_restraints     2115
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.1750
_refine_ls_R_factor_gt           0.0853
_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^)+(0.1267P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2166
_refine_ls_wR_factor_ref         0.2536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8019
_reflns_number_total             20423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02617_si_002.cif
_cod_data_source_block           1_a_pl
_cod_database_code               4128755
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.955
_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
2. Restrained distances
 P2-F8 \\sim P2-F8A
 with sigma of 0.02
 P2-F10 \\sim P2-F10A
 with sigma of 0.02
 P2-F12 \\sim P2-F12A
 with sigma of 0.02
 P2-F7 \\sim P2-F7A
 with sigma of 0.02
 P2-F11 \\sim P2-F11A
 with sigma of 0.02
 F19A-F21A \\sim F19A-F22A \\sim F19A-F23A \\sim F19A-F24A \\sim F20A-F21A
\\sim F20A-F22A \\sim F20A-
 F23A \\sim F20A-F24A \\sim F21A-F22A \\sim F22A-F24A \\sim F24A-F23A \\sim
F23A-F21A
 with sigma of 0.02
 P2-F9 \\sim P2-F9A
 with sigma of 0.02
 P1-F1 \\sim P1-F1A
 with sigma of 0.02
 P1-F2 \\sim P1-F2A
 with sigma of 0.02
 P1-F3 \\sim P1-F3A
 with sigma of 0.02
 P1-F4 \\sim P1-F4A
 with sigma of 0.02
 P1-F5 \\sim P1-F5A
 with sigma of 0.02
 P1-F6 \\sim P1-F6A
 with sigma of 0.02
 P3-F13 \\sim P3-F13A
 with sigma of 0.02
 P3-F14 \\sim P3-F14A
 with sigma of 0.02
 P3-F15 \\sim P3-F15A
 with sigma of 0.02
 P3-F16 \\sim P3-F16A
 with sigma of 0.02
 P3-F17 \\sim P3-F17A
 with sigma of 0.02
 P3-F18 \\sim P3-F18A
 with sigma of 0.02
 P4-F19 \\sim P4-F19A
 with sigma of 0.02
 P4-F21 \\sim P4-F21A
 with sigma of 0.02
 P4-F23 \\sim P4-F23A
 with sigma of 0.02
 P4-F22 \\sim P4-F22A
 with sigma of 0.02
 P4-F20 \\sim P4-F20A
 with sigma of 0.02
 P4-F24 \\sim P4-F24A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
P3 \\sim F13 \\sim F14 \\sim F15 \\sim F16 \\sim F17 \\sim F18 \\sim F13A \\sim
F14A \\sim F15A \\sim F16A \\sim F17A \\sim F18A \\sim P4 \\sim F19 \\sim F21
\\sim F23 \\sim F22 \\sim F20 \\sim F24 \\sim F19A \\sim F21A \\sim F23A \\sim
F22A \\sim F20A \\sim F24A \\sim P1 \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim
F5 \\sim F6 \\sim F1A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim F6A \\sim
P2 \\sim F8 \\sim F10 \\sim F12 \\sim F7 \\sim F11 \\sim F9 \\sim F8A \\sim
F10A \\sim F12A \\sim F7A \\sim F11A \\sim F9A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N1, N2, C1, H1, C2, H2, C3, H3, C4, H4, C5, C6, H6, C7, C8, C9, H9, C10, H10,
 C11, H11, C12, H12, C13, H13, C14, C15, C16, H16, C17, H17, C18, H18, C19, C20,
  H20, C21, C22, H22, C23, H23, C24, C25, H25, C26, H26, C27, H27A, H27B, C28,
 H28A, H28B, C29, H29, C30, H30, C31, H31, C32, C33, H33, C95, H95, C96, H96,
 C97, C98, C99, H99, C100, H100, C101, H101, C102, H102, N3, N4, C34, C35, H35,
 C36, H36, C37, C38, H38, C39, H39, C40, C41, H41, C42, C43, H43, C44, H44, C45,
  H45, C46, C47, H47, C48, H48, C49, H49, C50, H50, C51, C52, H52A, H52B, C53,
 C54, H54, C55, H55, C56, H56, C57, H57, C58, C59, C60, C61, C62, H62, C63, H63,
  C64, H64, C65, H65, C66, H66, C67, C69, H69, C70, H70, C71, H71, C72, H72,
 C73, C74, H74, C75, H75, C76, H76, C77, H77, C78, C79, H79A, H79B, C80, H80,
 C81, H81, C82, C83, H83, C84, H84, C85, C86, H86, C87, H87, C88, H88, C89, H89,
  C90, C91, C92, C93, H93, C94, H94, C228, H228
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P3, F13, F14, F15, F16, F17, F18, F13A, F14A, F15A, F16A, F17A, F18A, P4, F19,
  F21, F23, F22, F20, F24, F19A, F21A, F23A, F22A, F20A, F24A, P1, F1, F2, F3,
 F4, F5, F6, F1A, F2A, F3A, F4A, F5A, F6A, P2, F8, F10, F12, F7, F11, F9, F8A,
 F10A, F12A, F7A, F11A, F9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F8A)=Sof(F10A)=Sof(F12A)=Sof(F7A)=Sof(F11A)=Sof(F9A)=1-FVAR(1)
 Sof(F8)=Sof(F10)=Sof(F12)=Sof(F7)=Sof(F11)=Sof(F9)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(F16A)=Sof(F17A)=Sof(F18A)=1-FVAR(3)
 Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=Sof(F17)=Sof(F18)=FVAR(3)
 Sof(F19A)=Sof(F21A)=Sof(F23A)=Sof(F22A)=Sof(F20A)=Sof(F24A)=1-FVAR(4)
 Sof(F19)=Sof(F21)=Sof(F23)=Sof(F22)=Sof(F20)=Sof(F24)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C52(H52A,H52B), C79(H79A,H79B), C218(H21D,
 H21E), C220(H22A,H22B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C20(H20), C22(H22), C23(H23), C25(H25),
  C26(H26), C29(H29), C30(H30), C31(H31), C33(H33), C35(H35), C36(H36),
 C38(H38), C39(H39), C41(H41), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48),
  C49(H49), C50(H50), C54(H54), C55(H55), C56(H56), C57(H57), C62(H62),
 C63(H63), C64(H64), C65(H65), C66(H66), C69(H69), C70(H70), C71(H71), C72(H72),
  C74(H74), C75(H75), C76(H76), C77(H77), C80(H80), C81(H81), C83(H83),
 C84(H84), C86(H86), C87(H87), C88(H88), C89(H89), C93(H93), C94(H94), C95(H95),
  C96(H96), C99(H99), C100(H100), C101(H101), C102(H102), C228(H228)
6.c Idealised Me refined as rotating group:
 C217(H21A,H21B,H21C), C219(H21F,H21G,H21H)
;
_shelx_res_checksum              69799
_shelx_hkl_checksum              75236
_shelx_fab_checksum              76754
_olex2_submission_special_instructions 'No special instructions were received'