A synergy between the push‒pull electronic effect and twisted conformation for high-contrast mechanochromic AIEgens
Wang, Xiaoxuan; Qi, Chunxuan; Fu, Zhiyuan; Zhang, Haoke; Wang, Jianguo; Feng, Hai-Tao; Wang, Kai; Zou, Bo; Lam, Jacky W. Y.; Tang, Ben Zhong; Materials Horizons 8 (2021) 630–638; doi:10.1039/D0MH01251C

data_1559739
_publ_section_title
;
 A synergy between the push--pull electronic effect and twisted
 conformation for high-contrast mechanochromic AIEgens
;
_journal_issue                   2
_journal_name_full               'Materials Horizons'
_journal_page_first              630
_journal_page_last               638
_journal_paper_doi               10.1039/D0MH01251C
_journal_volume                  8
_journal_year                    2021
_chemical_formula_moiety
'3(F6 P), C38 H32 F6 N2 P, C38 H32 N2, C4 H4 O, C3 H3 O0.5'
_chemical_formula_sum            'C96.25 H87.5 Cl0 F0.25 N8.75 O8.75 P0.25'
_chemical_formula_weight         1519.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-03 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0790(7)
_cell_length_b                   30.1771(10)
_cell_length_c                   14.9963(5)
_cell_measurement_temperature    293(2)
_cell_volume                     8181.6(5)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            45912
_diffrn_reflns_point_group_measured_fraction_full 0.788
_diffrn_reflns_point_group_measured_fraction_max 0.766
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.943
_diffrn_reflns_theta_min         3.816
_exptl_absorpt_coefficient_mu    0.683
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             3209
_refine_diff_density_max         2.190
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.205
_refine_ls_abs_structure_details
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1203
_refine_ls_number_reflns         12726
_refine_ls_number_restraints     830
_refine_ls_restrained_S_all      2.168
_refine_ls_R_factor_all          0.2408
_refine_ls_R_factor_gt           0.2223
_refine_ls_shift/su_max          0.073
_refine_ls_shift/su_mean         0.006
_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          0.5377
_refine_ls_wR_factor_ref         0.5699
_reflns_Friedel_coverage         0.481
_reflns_Friedel_fraction_full    0.557
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                9774
_reflns_number_total             12726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0mh01251c2.cif
_cod_data_source_block           htao25cult
_cod_depositor_comments
'Adding full bibliography for 1559739--1559741.cif.'
_cod_original_formula_sum        'C96.25 H87.50 Cl0 F0.25 N8.75 O8.75 P0.25'
_cod_database_code               1559739
_shelx_shelxl_version_number     2018/3
_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
 C51-C50 = C51-C52 = C52-C53 = C58-C53 = C54-C53 = C54-C55 = C55-C50 = C58-C59
 = C57-C50 = C57-C56 = C56-C53 = C46-C40 = C47-C46 = C47-C01L = C48-C01L = C48-
 C49 = C49-C40 = C45-C40 = C44-C45 = C43-C44 = C43-C42 = C41-C42 = C41-C40 =
 C70-C61 = C63-C64 = C69-C70 = C62-C63 = C68-C67 = C65-C66 = C66-C61 = C62-C61 =
  C67-C61 = C69-C64 = C65-C64 = C78-C77 = C78-C79 = C79-C80 = C81-C80 = C85-C80
 = C85-C86 = C86-C77 = C84-C80 = C81-C82 = C83-C84 = C82-C77 = C83-C77
 1.45 with sigma of 0.01
 C02R-C02H = C02W-C02H = C02W-C02G = O01X-C02G = O01X-C02R = C3AA-C03C = C03I-
 C03C = C3AA-C03M = O03N-C03M
 1.45 with sigma of 0.01
 C03I-O03N
 1.45 with sigma of 0.01
 O03N-C3AA
 2.5 with sigma of 0.02
 P2-F7 = P2-F11 = P2-F10 = P2-F9 = P2-F12 = P2-F8
 1.6 with sigma of 0.02
 F10-F11
 2.6 with sigma of 0.02
 C40-C47
 2.4 with sigma of 0.02
 C46-C01L
 2.4 with sigma of 0.02
 C47-C48
 2.4 with sigma of 0.02
 C01L-C49
 2.4 with sigma of 0.02
 C48-C40
 2.4 with sigma of 0.02
 F7-F11
 2.6 with sigma of 0.02
 F11-F8
 2.6 with sigma of 0.02
3. Restrained planarity
 C03I, C03C, C3AA, O03N, C03M
 with sigma of 0.01
 C64, C65, C63, C66, C62, C61
 with sigma of 0.01
 C67, C68, C64, C69, C70, C61
 with sigma of 0.01
 C77, C82, C81, C80, C79, C78
 with sigma of 0.01
 C77, C83, C84, C80, C85, C86
 with sigma of 0.01
 C40, C49, C48, C01L, C47, C46
 with sigma of 0.01
 C41, C40, C42, C43, C44, C45
 with sigma of 0.01
 C50, C51, C52, C53, C54, C55
 with sigma of 0.01
 C50, C57, C56, C53, C58, C59
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C03C \\sim C03I \\sim C03M \\sim O03N \\sim C3AA: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
O01X \\sim C02G \\sim C02H \\sim C02R \\sim C02W: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
Uanis(C30) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C32)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C5) \\sim Ueq,
Uanis(C2) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C74) \\sim Ueq, Uanis(C34) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C1)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C76) \\sim Ueq,
Uanis(C4) \\sim Ueq, Uanis(C75) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C01L) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C53)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C31) \\sim Ueq,
Uanis(C77) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C72)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C90) \\sim Ueq,
Uanis(C10) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C89)
\\sim Ueq, Uanis(C87) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C26) \\sim Ueq,
Uanis(C02G) \\sim Ueq, Uanis(C02H) \\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C92)
\\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(C02R) \\sim Ueq, Uanis(C24) \\sim Ueq,
Uanis(C02W) \\sim Ueq, Uanis(C82) \\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(C67)
\\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C63) \\sim Ueq,
Uanis(C56) \\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C03C) \\sim Ueq, Uanis(C78)
\\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C70) \\sim Ueq,
Uanis(C03I) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C03M) \\sim Ueq, Uanis(C58)
\\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C55) \\sim Ueq,
Uanis(C54) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C86)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C84) \\sim Ueq,
Uanis(C45) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C52)
\\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C3AA) \\sim Ueq, Uanis(C43) \\sim Ueq,
Uanis(C41) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C48) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C03C) \\sim Ueq, Uanis(C03I) \\sim Ueq, Uanis(C03M) \\sim Ueq,
Uanis(O03N) \\sim Ueq, Uanis(C3AA) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C3) = Uanis(C4) = Uanis(C5)
5. Rigid body (RIGU) restrains
 C03C, C03I, C03M, O03N, C3AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O01X, C02G, C02R, C02W, C02H
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Fixed Sof: C01L(0.5) H01L(0.5) H53A(0.5) H53(0.5) C82(0.5) H82(0.5) C79(0.5)
 H11(0.5) C67(0.5) H67(0.5) C59(0.5) H59(0.5) C46(0.5) H46(0.5) C63(0.5)
 H63(0.5) C56(0.5) H56(0.5) C81(0.5) H81(0.5) C78(0.5) H78(0.5) C57(0.5)
 H57(0.5) C68(0.5) H68(0.5) C70(0.5) H70(0.5) C03I(0.5) H03I(0.5) C47(0.5)
 H47(0.5) C03M(0.5) H03M(0.5) O03N(0.5) C58(0.5) H58(0.5) C49(0.5) H49(0.5)
 C62(0.5) H62(0.5) C55(0.5) H55(0.5) C54(0.5) H54(0.5) C83(0.5) H83(0.5)
 C85(0.5) H85(0.5) C86(0.5) H86(0.5) C42(0.5) H42(0.5) C51(0.5) H51(0.5)
 C84(0.5) H84(0.5) C45(0.5) H45(0.5) C65(0.5) H65(0.5) C66(0.5) H66(0.5)
 C52(0.5) H52(0.5) C69(0.5) H69(0.5) C43(0.5) H43(0.5) C41(0.5) H41(0.5)
 C44(0.5) H44(0.5) C48(0.5) H48(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C28(H28), C29(H29), C20(H20), C17(H17), C32(H32), C37(H37), C5(H5), C2(H2),
 C9(H9), C74(H74), C34(H34), C12(H12), C73(H73), C16(H16), C3(H3), C6(H6),
 C4(H4), C75(H75), C11(H11A), C8(H8), C01L(H01L), C19(H19), C36(H36), C53(H53A),
  C53(H53), C22(H22), C31(H31), C72(H72), C35(H35), C25(H25), C90(H90),
 C10(H10), C23(H23), C88(H88), C89(H89), C02G(H02G), C02H(H02H), C91(H91),
 C02R(H02R), C24(H24), C02W(H02W), C82(H82), C79(H11), C67(H67), C59(H59),
 C46(H46), C63(H63), C56(H56), C81(H81), C03C(H03C), C78(H78), C57(H57),
 C68(H68), C70(H70), C03I(H03I), C47(H47), C03M(H03M), C58(H58), C49(H49),
 C62(H62), C55(H55), C54(H54), C83(H83), C85(H85), C86(H86), C42(H42), C51(H51),
  C84(H84), C45(H45), C65(H65), C66(H66), C52(H52), C69(H69), C3AA(H3AA),
 C43(H43), C41(H41), C44(H44), C48(H48)
7.b Idealised Me refined as rotating group:
 C76(H76A,H76B,H76C), C38(H38A,H38B,H38C), C26(H26A,H26B,H26C), C92(H92A,H92B,
 H92C)
;
_shelx_res_checksum              34680
_olex2_submission_special_instructions 'No special instructions were received'