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_7134973
_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_absolute_configuration unk
_chemical_formula_moiety         'C87 H88 N2 O8, C5 H12 O'
_chemical_formula_sum            'C92 H100 N2 O9'
_chemical_formula_weight         1377.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 113.871(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5858(7)
_cell_length_b                   21.7012(7)
_cell_length_c                   20.0122(7)
_cell_measurement_reflns_used    7168
_cell_measurement_temperature    149.99(11)
_cell_measurement_theta_max      72.5860
_cell_measurement_theta_min      2.3880
_cell_volume                     7778.3(5)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.924
_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    -62.00 -25.00   0.50    5.00    --  -45.30 128.00 -84.00   74
  2  \w   -104.00 -52.00   0.50    5.00    --  -45.30 141.00  87.00  104
  3  \w   -108.00 -72.00   0.50    5.00    --  -45.30-141.00  29.00   72
  4  \w     67.00  92.00   0.50    5.00    --   45.30 141.00  87.00   50
  5  \w   -102.00 -73.00   0.50    1.30    -- -100.00 141.00  87.00   58
  6  \w   -146.00-121.00   0.50    1.30    -- -100.00-141.00  29.00   50
  7  \w   -171.00 -80.00   0.50    1.30    -- -100.00-128.00-158.00  182
  8  \w   -111.00 -79.00   0.50    1.30    -- -100.00 128.00 -84.00   64
  9  \w     56.00  81.00   0.50    1.30    --  109.64-141.00  29.00   50
 10  \w     52.00  77.00   0.50    1.30    --  109.64-128.00-158.00   50
 11  \w     86.00 129.00   0.50    1.30    --  109.64 128.00 -84.00   86
 12  \w    -30.00  34.00   0.50    5.00    --  -45.30  19.00  60.00  128
 13  \w    -10.00  19.00   0.50    5.00    --   45.30 -19.00-150.00   58
 14  \w    -29.00  22.00   0.50    5.00    --   45.30 -19.00-180.00  102
 15  \w     -3.00  23.00   0.50    5.00    --   45.30 -19.00  90.00   52
 16  \w   -152.00-122.00   0.50    1.30    -- -100.00-125.00 -30.00   60
 17  \w   -117.00 -88.00   0.50    1.30    -- -100.00-125.00 -30.00   58
 18  \w    -54.00 -27.00   0.50    1.30    -- -100.00  45.00  60.00   54
 19  \w    -61.00 -35.00   0.50    1.30    -- -100.00 125.00-150.00   52
 20  \w   -177.00-146.00   0.50    1.30    -- -100.00 -30.00  30.00   62
 21  \w   -124.00 -81.00   0.50    1.30    -- -100.00 -30.00  30.00   86
 22  \w    -88.00 -26.00   0.50    1.30    -- -100.00  77.00 -60.00  124
 23  \w   -126.00 -99.00   0.50    1.30    -- -100.00 -94.00  60.00   54
 24  \w    -74.00 -37.00   0.50    1.30    -- -100.00  61.00 150.00   74
 25  \w   -111.00 -29.00   0.50    1.30    -- -100.00 125.00-180.00  164
 26  \w   -167.00-137.00   0.50    1.30    -- -100.00 -94.00  60.00   60
 27  \w    -50.00 -25.00   0.50    1.30    -- -100.00  45.00  30.00   50
 28  \w    -51.00 -26.00   0.50    1.30    -- -100.00  45.00 150.00   50
 29  \w   -111.00 -79.00   0.50    1.30    -- -100.00 125.00-150.00   64
 30  \w    -53.00 -26.00   0.50    1.30    -- -100.00  45.00  90.00   54
 31  \w     47.00 101.00   0.50    1.30    --  109.64 -77.00   0.00  108
;
_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      0.0220656000
_diffrn_orient_matrix_UB_12      -0.0372383000
_diffrn_orient_matrix_UB_13      0.0712343000
_diffrn_orient_matrix_UB_21      -0.0181506000
_diffrn_orient_matrix_UB_22      -0.0603235000
_diffrn_orient_matrix_UB_23      -0.0443556000
_diffrn_orient_matrix_UB_31      0.0811311000
_diffrn_orient_matrix_UB_32      -0.0033827000
_diffrn_orient_matrix_UB_33      0.0067909000
_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  0.0730
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29706
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.769
_diffrn_reflns_theta_min         2.414
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71179
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       block
_exptl_crystal_F_000             2952
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(11)
_refine_ls_extinction_coef       0.00039(4)
_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   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1056
_refine_ls_number_reflns         13725
_refine_ls_number_restraints     305
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0698P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.832
_reflns_Friedel_fraction_max     0.743
_reflns_number_gt                8584
_reflns_number_total             13725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03945b2.cif
_cod_data_source_block           qxg-p5nn2_0513_auto
_cod_depositor_comments
'Adding full bibliography for 7134972--7134974.cif.'
_cod_database_code               7134973
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O6 \\sim C74 \\sim C75 \\sim C74A \\sim C75A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
O9 \\sim C88 \\sim C89 \\sim C90 \\sim C91 \\sim C92 \\sim O9A \\sim C88A \\sim
C89A \\sim C90A \\sim C91A \\sim C92A: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
O3 \\sim C61 \\sim C62 \\sim C61A \\sim C62A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
O8 \\sim C85 \\sim C86 \\sim C85A \\sim C86A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
3. Same fragment restrains
{O3, C61A, C62A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{O3, C61, C62}
{O6, C74A, C75A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{O6, C74, C75}
{O8, C85A, C86A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{O8, C85, C86}
{O9, C88A, C89A, C90A, C91A, C92A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{O9, C88, C89, C90, C91, C92}
4. Others
 Sof(C61A)=Sof(H61C)=Sof(H61D)=Sof(C62A)=Sof(H62D)=Sof(H62E)=Sof(H62F)=1-FVAR(1)
 Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=FVAR(1)
 Sof(C74A)=Sof(H74C)=Sof(H74D)=Sof(C75A)=Sof(H75D)=Sof(H75E)=Sof(H75F)=1-FVAR(2)
 Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(C75)=Sof(H75A)=Sof(H75B)=Sof(H75C)=FVAR(2)
 Sof(O9A)=Sof(H9AA)=Sof(C88A)=Sof(H88D)=Sof(H88E)=Sof(H88F)=Sof(C89A)=
 Sof(H89A)=Sof(C90A)=Sof(H90C)=Sof(H90D)=Sof(C91A)=Sof(H91C)=Sof(H91D)=
 Sof(C92A)=Sof(H92D)=Sof(H92E)=Sof(H92F)=1-FVAR(3)
 Sof(O9)=Sof(H9A)=Sof(C88)=Sof(H88A)=Sof(H88B)=Sof(H88C)=Sof(C89)=Sof(H89)=
 Sof(C90)=Sof(H90A)=Sof(H90B)=Sof(C91)=Sof(H91A)=Sof(H91B)=Sof(C92)=Sof(H92A)=
 Sof(H92B)=Sof(H92C)=FVAR(3)
 Sof(C85A)=Sof(H85C)=Sof(H85D)=Sof(C86A)=Sof(H86D)=Sof(H86E)=Sof(H86F)=1-FVAR(4)
 Sof(C85)=Sof(H85A)=Sof(H85B)=Sof(C86)=Sof(H86A)=Sof(H86B)=Sof(H86C)=FVAR(4)
5.a Riding coordinates:
 O9(H9A), O9A(H9AA)
5.b Ternary CH refined with riding coordinates:
 C89(H89), C89A(H89A)
5.c Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C74(H74A,H74B), C85(H85A,H85B), C43(H43A,H43B), C50(H50A,
 H50B), C52(H52A,H52B), C54(H54A,H54B), C63(H63A,H63B), C65(H65A,H65B),
 C72(H72A,H72B), C76(H76A,H76B), C83(H83A,H83B), C87(H87A,H87B), C85A(H85C,
 H85D), C90(H90A,H90B), C91(H91A,H91B), C61A(H61C,H61D), C74A(H74C,H74D),
 C90A(H90C,H90D), C91A(H91C,H91D)
5.d 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)
5.e Idealised Me refined as rotating group:
 C62(H62A,H62B,H62C), C75(H75A,H75B,H75C), C86(H86A,H86B,H86C), C51(H51A,H51B,
 H51C), C53(H53A,H53B,H53C), C64(H64A,H64B,H64C), C73(H73A,H73B,H73C), C84(H84A,
 H84B,H84C), C86A(H86D,H86E,H86F), C88(H88A,H88B,H88C), C92(H92A,H92B,H92C),
 C62A(H62D,H62E,H62F), C75A(H75D,H75E,H75F), C88A(H88D,H88E,H88F), C92A(H92D,
 H92E,H92F)
;
_shelx_res_checksum              35441
_shelx_hkl_checksum              11930
_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 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.400