Superstructure-induced enhancement of solid-state triphenylacrylonitrile photochromism <i>via</i> a macrocycle-mediated blocking strategy.
Li, Meng-Hao; Hui, Hui; Wang, Yan; Yang, Ying-Wei; Chemical science 17 (2026) 5745–5757; doi:10.1039/d5sc08539j

data_1576897
_publ_section_title
;
 Superstructure-induced enhancement of solid-state triphenylacrylonitrile
 photochromism <i>via</i> a macrocycle-mediated blocking strategy.
;
_journal_issue                   11
_journal_name_full               'Chemical science'
_journal_page_first              5745
_journal_page_last               5757
_journal_paper_doi               10.1039/d5sc08539j
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety
'C H2 Cl2, C85 H72 N2 O8, 0.75(C2 H4 O2), 0.75(C2 H3 O2), 0.6[H2O]'
_chemical_formula_sum            'C90 H82 Cl2 N2 O12'
_chemical_formula_weight         1454.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-19
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-09-24 deposited with the CCDC.	2026-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 132.234(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   45.8868(17)
_cell_length_b                   13.1150(5)
_cell_length_c                   33.8049(13)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.38
_cell_measurement_theta_min      3.53
_cell_volume                     15062.8(11)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            89425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.703
_diffrn_reflns_theta_min         2.601
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.308
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6566
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1095 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.8719.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             6128
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1137
_refine_ls_number_reflns         13866
_refine_ls_number_restraints     628
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1384P)^2^+8.0119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9926
_reflns_number_total             13866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08539j2.cif
_cod_data_source_block           TPAN-P5-CH3COOH
_cod_original_cell_volume        15062.8(10)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1576897
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.808
_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, All O(H) groups
2. Restrained distances
 O9-C87 = O10-C87
 1.26 with sigma of 0.02
 C98-C97
 1.54 with sigma of 0.01
 O19-C98
 2.5 with sigma of 0.01
 O20-C98
 2.5 with sigma of 0.01
 C87-C88
 1.5 with sigma of 0.02
 C95-C96
 1.54 with sigma of 0.01
 O11-C89 = O12-C89
 1.26 with sigma of 0.02
 C89-C90
 1.5 with sigma of 0.02
 O17-C95 = O18-C95
 1.26 with sigma of 0.02
 C95-O18
 1.45 with sigma of 0.01
 O19-C97
 1.45 with sigma of 0.01
 O20-C97
 1.2 with sigma of 0.01
 O18-O17
 2.3 with sigma of 0.01
 O16-C94
 1.2 with sigma of 0.01
 O15-C94
 1.45 with sigma of 0.01
 O17-C96
 2.38 with sigma of 0.04
 O18-C96
 2.39 with sigma of 0.04
 O10-C88
 2.39 with sigma of 0.04
 O9-C88
 2.38 with sigma of 0.04
 O9-O10
 2.19 with sigma of 0.04
 O11-O12
 2.19 with sigma of 0.04
 O11-C90
 2.38 with sigma of 0.04
 O12-C90
 2.39 with sigma of 0.04
 O17-O18
 2.19 with sigma of 0.04
 C95-C96 \\sim C97-C98
 with sigma of 0.02
 O17-C96 \\sim O19-C98
 with sigma of 0.04
 O18-C96 \\sim O20-C98
 with sigma of 0.04
 O10-C88 \\sim O16-C93
 with sigma of 0.04
 O10-C87 \\sim O16-C94
 with sigma of 0.02
 O17-C96 \\sim C96-O18
 with sigma of 0.04
 O9-O10 \\sim O15-O16
 with sigma of 0.04
 O9-C88 \\sim C88-O10
 with sigma of 0.04
 C87-O9 \\sim C87-O10
 with sigma of 0.02
 C87-C88 \\sim C94-C93
 with sigma of 0.02
 O9-C88 \\sim O15-C93
 with sigma of 0.04
 C89-O11 \\sim C89-O12
 with sigma of 0.02
 O11-C90 \\sim C90-O12
 with sigma of 0.04
 O11-C89 \\sim O13-C91
 with sigma of 0.02
 O12-C89 \\sim O14-C91
 with sigma of 0.02
 C89-C90 \\sim C91-C92
 with sigma of 0.02
 O11-O12 \\sim O13-O14
 with sigma of 0.04
 O11-C90 \\sim O13-C92
 with sigma of 0.04
 O12-C90 \\sim O14-C92
 with sigma of 0.04
 O9-C87 \\sim O15-C94
 with sigma of 0.02
 C95-O17 \\sim C95-O18
 with sigma of 0.02
 O17-C95 \\sim O19-C97
 with sigma of 0.02
 O18-C95 \\sim O20-C97
 with sigma of 0.02
 O17-O18 \\sim O19-O20
 with sigma of 0.04
 Cl1-C86 \\sim Cl3-C99
 with sigma of 0.02
 Cl2-C86 \\sim Cl4-C99
 with sigma of 0.02
 Cl1-Cl2 \\sim Cl3-Cl4
 with sigma of 0.04
3. Restrained planarity
 O17, O18, C95, C96
 with sigma of 0.1
 O9, O10, C87, C88
 with sigma of 0.1
 O11, O12, C89, C90
 with sigma of 0.1
4. Rigid bond restraints
 C94, O16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
O19 \\sim C97 \\sim O20 \\sim C98 \\sim C96 \\sim O17 \\sim C95 \\sim O18:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O17 \\sim O18 \\sim C95 \\sim C96: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C88 \\sim O9 \\sim C87 \\sim O10 \\sim O15 \\sim C93 \\sim C94 \\sim O16:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O9 \\sim O10 \\sim C87 \\sim C88: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
O11 \\sim O12 \\sim C89 \\sim C90: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C92 \\sim C91 \\sim O13 \\sim O14 \\sim C90 \\sim O11 \\sim C89 \\sim O12:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O16 \\sim C93 \\sim C94 \\sim O15 \\sim O17 \\sim C95 \\sim O18 \\sim C96 \\sim
O10 \\sim O9 \\sim C87 \\sim C88 \\sim O19 \\sim C97 \\sim O20 \\sim C98:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O20) \\sim Ueq, Uanis(O19) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C98)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C95) \\sim Ueq, Uanis(O17) \\sim Ueq, Uanis(O18) \\sim Ueq, Uanis(C96)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C87) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(C88)
\\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(C94) \\sim Ueq, Uanis(O15) \\sim Ueq,
Uanis(O16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O12) \\sim Ueq, Uanis(O11) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(C90)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C94) \\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(O15) \\sim Ueq, Uanis(O16)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Rigid body (RIGU) restrains
 O17, O18, C95, C96
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O9, O10, C87, C88
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O11, O12, C89, C90
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) C86(0.5) H86A(0.5) H86B(0.5) O9(0.35) O10(0.35)
 H10(0.35) C87(0.35) C88(0.35) H88A(0.35) H88B(0.35) H88C(0.35) O11(0.25)
 H11A(0.25) O12(0.25) C89(0.25) C90(0.25) H90A(0.25) H90B(0.25) H90C(0.25)
 C91(0.25) O13(0.25) O14(0.25) H14(0.25) C92(0.25) H92A(0.25) H92B(0.25)
 H92C(0.25) C93(0.3) H93A(0.3) H93B(0.3) H93C(0.3) O15(0.3) H15(0.3) C94(0.3)
 O16(0.3) O17(0.5) O18(0.5) H18A(0.5) C95(0.5) C96(0.5) H96A(0.5) H96B(0.5)
 H96C(0.5) O19(0.35) H19(0.35) C97(0.35) O20(0.35) C98(0.35) H98A(0.35)
 H98B(0.35) H98C(0.35) C99(0.5) H99A(0.5) H99B(0.5) Cl3(0.5) Cl4(0.5)
8.a Riding coordinates:
 O10(H10), C88(H88A,H88B,H88C), C96(H96A,H96B,H96C), C98(H98A,H98B,H98C)
8.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C30(H30A,H30B), C36(H36A,H36B), C54(H54A,H54B), C65(H65A,
 H65B), C86(H86A,H86B), C99(H99A,H99B)
8.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C11(H11), C18(H18), C22(H22), C24(H24), C26(H26), C27(H27),
 C28(H28), C34(H34), C35(H35), C37(H37), C41(H41), C43(H43), C45(H45), C48(H48),
  C50(H50), C52(H52), C53(H53), C55(H55), C56(H56), C60(H60), C61(H61),
 C62(H62), C63(H63), C64(H64), C66(H66), C67(H67), C68(H68), C69(H69), C72(H72),
  C73(H73), C74(H74), C76(H76), C77(H77), C79(H79), C80(H80), C81(H81)
8.d Tetrahedral OH refined with riding coordinates:
 O11(H11A), O14(H14), O15(H15), O18(H18A), O19(H19)
8.e Idealised Me refined as rotating group:
 C70(H70A,H70B,H70C), C71(H71A,H71B,H71C), C75(H75A,H75B,H75C), C78(H78A,H78B,
 H78C), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C85(H85A,
 H85B,H85C), C90(H90A,H90B,H90C), C92(H92A,H92B,H92C), C93(H93A,H93B,H93C)
;
_shelx_res_checksum              682
_olex2_submission_special_instructions 'No special instructions were received'