Guest-triggered crystallization of π-conjugated pillar[5]arene: from amorphous aggregates to an ordered architecture <i>via</i> solid-state host-guest synergy.
Chen, Jin-Fa; Gao, Qing-Xiu; Wang, Yuxuan; Shi, Bingbing; Yao, Hong; Wei, Tai-Bao; Lin, Qi; Chemical communications (Cambridge, England) 61 (2025) 15882–15885; doi:10.1039/d5cc03945b

data_7134972
_publ_section_title
;
 Guest-triggered crystallization of &#x3c0;-conjugated pillar[5]arene:
 from amorphous aggregates to an ordered architecture <i>via</i>
 solid-state host-guest synergy.
;
_journal_issue                   81
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15882
_journal_page_last               15885
_journal_paper_doi               10.1039/d5cc03945b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C87 H88 N2 O8, 3.844[C3H6O]'
_chemical_formula_sum            'C98.53 H111.06 N2 O11.84'
_chemical_formula_weight         1512.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-08-06
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-08-29 deposited with the CCDC.	2025-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                64.6808(7)
_cell_angle_beta                 70.8779(7)
_cell_angle_gamma                74.2696(6)
_cell_formula_units_Z            4
_cell_length_a                   16.74959(13)
_cell_length_b                   24.61558(16)
_cell_length_c                   24.87337(16)
_cell_measurement_reflns_used    57047
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.2920
_cell_measurement_theta_min      1.9980
_cell_volume                     8655.00(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -119.00 -25.00   0.50    1.50    --  -45.27 -42.00-146.00  188
  2  \w    -42.00  12.00   0.50    1.50    --  -45.27  42.00   6.00  108
  3  \w     73.00  99.00   0.50    1.50    --   45.27  42.00   6.00   52
  4  \w    -26.00  43.00   0.50    1.50    --   45.27 -42.00-146.00  138
  5  \w   -175.00 -79.00   0.50    4.00    -- -100.00 -42.00-146.00  192
  6  \w     89.00 172.00   0.50    4.00    --  109.64  42.00   6.00  166
  7  \w    -71.00 -29.00   0.50    1.50    --  -45.27 125.00 120.00   84
  8  \w     17.00  83.00   0.50    1.50    --   45.27-125.00-180.00  132
  9  \w    -24.00  71.00   0.50    1.50    --   45.27 -77.00 -30.00  190
 10  \w    -29.00  -3.00   0.50    1.50    --   45.27 -19.00-180.00   52
 11  \w    -33.00  20.00   0.50    1.50    --   45.27 -19.00 -90.00  106
 12  \w   -177.00-115.00   0.50    4.00    -- -100.00 -30.00  90.00  124
 13  \w   -155.00 -88.00   0.50    4.00    -- -100.00 -94.00 -60.00  134
 14  \w   -111.00 -83.00   0.50    4.00    -- -100.00 125.00 -60.00   56
 15  \w   -158.00 -82.00   0.50    4.00    -- -100.00-125.00-180.00  152
 16  \w    -64.00 -35.00   0.50    4.00    -- -100.00  77.00 -90.00   58
 17  \w   -109.00 -38.00   0.50    4.00    -- -100.00  77.00-180.00  142
 18  \w    -73.00 -42.00   0.50    4.00    -- -100.00  61.00  90.00   62
 19  \w   -121.00 -93.00   0.50    4.00    -- -100.00 138.00 124.31   56
 20  \w    -96.00 -50.00   0.50    4.00    -- -100.00 125.00 -30.00   92
 21  \w   -112.00 -67.00   0.50    4.00    -- -100.00 125.00-180.00   90
 22  \w    -67.00 -31.00   0.50    4.00    -- -100.00 125.00   0.00   72
 23  \w    -70.00 -31.00   0.50    4.00    -- -100.00 138.00 124.31   78
 24  \w   -111.00 -74.00   0.50    4.00    -- -100.00 125.00 120.00   74
 25  \w    -54.00 -26.00   0.50    4.00    -- -100.00  45.00 120.00   56
 26  \w   -106.00 -80.00   0.50    4.00    -- -100.00 -30.00  90.00   52
 27  \w    -54.00 -26.00   0.50    4.00    -- -100.00  45.00  90.00   56
 28  \w    -53.00 -25.00   0.50    4.00    -- -100.00  45.00 -90.00   56
 29  \w    -90.00 -29.00   0.50    4.00    -- -100.00 125.00-120.00  122
 30  \w    -52.00 -25.00   0.50    4.00    -- -100.00  45.00-180.00   54
 31  \w    -93.00 -35.00   0.50    4.00    -- -100.00 125.00 150.00  116
 32  \w   -111.00 -65.00   0.50    4.00    -- -100.00 125.00 -90.00   92
 33  \w   -126.00 -78.00   0.50    4.00    -- -100.00 144.00  11.67   96
 34  \w    -54.00 -25.00   0.50    4.00    -- -100.00  45.00 150.00   58
 35  \w    112.00 145.00   0.50    4.00    --  109.64  61.00-120.00   66
 36  \w     36.00  68.00   0.50    4.00    --  109.64 -61.00 120.00   64
 37  \w     56.00 103.00   0.50    4.00    --  109.64 -94.00  60.00   94
 38  \w    131.00 157.00   0.50    4.00    --  109.64  77.00 -60.00   52
 39  \w     94.00 120.00   0.50    4.00    --  109.64  77.00 -60.00   52
 40  \w     82.00 163.00   0.50    4.00    --  109.64 125.00  90.00  162
 41  \w     49.00  91.00   0.50    4.00    --  109.64-125.00  60.00   84
 42  \w     92.00 142.00   0.50    4.00    --  109.64  45.00 120.00  100
 43  \w     47.00 103.00   0.50    4.00    --  109.64 -94.00-150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0922377000
_diffrn_orient_matrix_UB_12      -0.0125251000
_diffrn_orient_matrix_UB_13      0.0175941000
_diffrn_orient_matrix_UB_21      -0.0272656000
_diffrn_orient_matrix_UB_22      0.0346478000
_diffrn_orient_matrix_UB_23      0.0436903000
_diffrn_orient_matrix_UB_31      -0.0213006000
_diffrn_orient_matrix_UB_32      0.0595966000
_diffrn_orient_matrix_UB_33      -0.0526457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            113849
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.625
_diffrn_reflns_theta_min         2.009
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             3244
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2013
_refine_ls_number_reflns         34167
_refine_ls_number_restraints     883
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+1.8615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                29447
_reflns_number_total             34167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03945b2.cif
_cod_data_source_block           gaoqxiu_0921_2_auto
_cod_depositor_comments
'Adding full bibliography for 7134972--7134974.cif.'
_cod_original_cell_volume        8655.01(12)
_cod_database_code               7134972
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C162-C161 = C195-C194
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C141 \\sim C163 \\sim O11 \\sim O12 \\sim O13 \\sim O14 \\sim C142 \\sim C143
\\sim C144 \\sim C145 \\sim C146 \\sim C147 \\sim C148 \\sim C149 \\sim C150
\\sim C151 \\sim C152 \\sim C153 \\sim C154 \\sim C155 \\sim C156 \\sim C157
\\sim C158 \\sim C159 \\sim C160 \\sim C161 \\sim C162 \\sim O11A \\sim O12A
\\sim O13A \\sim O14A \\sim C175 \\sim C176 \\sim C177 \\sim C178 \\sim C179
\\sim C180 \\sim C181 \\sim C182 \\sim C183 \\sim C184 \\sim C185 \\sim C186
\\sim C187 \\sim C188 \\sim C189 \\sim C190 \\sim C191 \\sim C192 \\sim C193
\\sim C194 \\sim C195: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Same fragment restrains
{C141, C163, O11A, O12A, O13A, O14A, C175, C176, C177, C178, C179, C180, C181,
C182, C183, C184, C185, C186, C187, C188, C189, C190, C191, C192, C193, C194,
C195} sigma for 1-2: 0.01, 1-3: 0.04
as in
{C141, C163, O11, O12, O13, O14, C142, C143, C144, C145, C146, C147, C148,
C149, C150, C151, C152, C153, C154, C155, C156, C157, C158, C159, C160, C161,
C162}
5. Others
 Sof(H14F)=Sof(H14G)=Sof(H16C)=Sof(H16D)=Sof(O11A)=Sof(O12A)=Sof(O13A)=
 Sof(O14A)=Sof(C175)=Sof(C176)=Sof(C177)=Sof(H177)=Sof(C178)=Sof(C179)=
 Sof(C180)=Sof(H180)=Sof(C181)=Sof(H18A)=Sof(H18B)=Sof(C182)=Sof(H18C)=
 Sof(H18D)=Sof(H18E)=Sof(C183)=Sof(H18F)=Sof(H18G)=Sof(C184)=Sof(H18H)=
 Sof(H18I)=Sof(H18J)=Sof(C185)=Sof(H18K)=Sof(H18L)=Sof(C186)=Sof(C187)=
 Sof(C188)=Sof(H188)=Sof(C189)=Sof(C190)=Sof(C191)=Sof(H191)=Sof(C192)=
 Sof(H19A)=Sof(H19B)=Sof(C193)=Sof(H19C)=Sof(H19D)=Sof(H19E)=Sof(C194)=
 Sof(H19F)=Sof(H19G)=Sof(C195)=Sof(H19H)=Sof(H19I)=Sof(H19J)=1-FVAR(1)
 Sof(H14D)=Sof(H14E)=Sof(H16A)=Sof(H16B)=Sof(O11)=Sof(O12)=Sof(O13)=Sof(O14)=
 Sof(C142)=Sof(C143)=Sof(C144)=Sof(H144)=Sof(C145)=Sof(C146)=Sof(C147)=
 Sof(H147)=Sof(C148)=Sof(H14H)=Sof(H14I)=Sof(C149)=Sof(H14J)=Sof(H14K)=
 Sof(H14L)=Sof(C150)=Sof(H15A)=Sof(H15B)=Sof(C151)=Sof(H15C)=Sof(H15D)=
 Sof(H15E)=Sof(C152)=Sof(H15F)=Sof(H15G)=Sof(C153)=Sof(C154)=Sof(C155)=
 Sof(H155)=Sof(C156)=Sof(C157)=Sof(C158)=Sof(H158)=Sof(C159)=Sof(H15H)=
 Sof(H15I)=Sof(C160)=Sof(H16E)=Sof(H16F)=Sof(H16G)=Sof(C161)=Sof(H16H)=
 Sof(H16I)=Sof(C162)=Sof(H16J)=Sof(H16K)=Sof(H16L)=FVAR(1)
 Fixed Sof: C61(0.5) H61A(0.5) H61B(0.5) C62(0.5) H62A(0.5) H62B(0.5)
 H62C(0.5) C61A(0.5) H61C(0.5) H61D(0.5) C62A(0.5) H62D(0.5) H62E(0.5) H62F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C50(H50A,H50B), C52(H52A,H52B), C54(H54A,H54B), C63(H63A,
 H63B), C65(H65A,H65B), C72(H72A,H72B), C74(H74A,H74B), C76(H76A,H76B),
 C83(H83A,H83B), C85(H85A,H85B), C87(H87A,H87B), C61(H61A,H61B), C61A(H61C,
 H61D), C130(H13A,H13B), C137(H13C,H13D), C139(H13H,H13I), C141(H14D,H14E),
 C141(H14F,H14G), C163(H16A,H16B), C163(H16C,H16D), C148(H14H,H14I), C150(H15A,
 H15B), C152(H15F,H15G), C159(H15H,H15I), C161(H16H,H16I), C170(H17A,H17B),
 C172(H17F,H17G), C174(H17K,H17L), C181(H18A,H18B), C183(H18F,H18G), C185(H18K,
 H18L), C192(H19A,H19B), C194(H19F,H19G)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C26(H26), C27(H27), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34),
 C35(H35), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C46(H46),
  C49(H49), C57(H57), C60(H60), C68(H68), C71(H71), C79(H79), C82(H82),
 C90(H90), C93(H93), C95(H95), C96(H96), C98(H98), C99(H99), C101(H101),
 C102(H102), C103(H103), C104(H104), C105(H105), C107(H107), C108(H108),
 C109(H109), C110(H110), C111(H111), C113(H113), C114(H114), C116(H116),
 C117(H117), C119(H119), C120(H120), C121(H121), C122(H122), C123(H123),
 C125(H125), C126(H126), C127(H127), C128(H128), C129(H129), C133(H133),
 C136(H136), C144(H144), C147(H147), C155(H155), C158(H158), C166(H166),
 C169(H169), C177(H177), C180(H180), C188(H188), C191(H191)
6.c Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C53(H53A,H53B,H53C), C64(H64A,H64B,H64C), C73(H73A,H73B,
 H73C), C75(H75A,H75B,H75C), C84(H84A,H84B,H84C), C86(H86A,H86B,H86C), C62(H62A,
 H62B,H62C), C62A(H62D,H62E,H62F), C138(H13E,H13F,H13G), C140(H14A,H14B,H14C),
 C149(H14J,H14K,H14L), C151(H15C,H15D,H15E), C160(H16E,H16F,H16G), C162(H16J,
 H16K,H16L), C171(H17C,H17D,H17E), C173(H17H,H17I,H17J), C182(H18C,H18D,H18E),
 C184(H18H,H18I,H18J), C193(H19C,H19D,H19E), C195(H19H,H19I,H19J)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 492 electrons were 
found in a volume of 2122\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
3.844[C3H6O] per Asymmetric Unit 
which account for 492 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              6945
_shelx_hkl_checksum              56843
_shelx_fab_checksum              39139
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.821
_oxdiff_exptl_absorpt_empirical_full_min 0.466