A calix[3]carbazole-based cavitand: synthesis, structure and its complexation with fullerenes.
Zhang, Fan; Du, Xu-Sheng; Song, Kui-Zhu; Han, Ying; Lu, Hai-Yan; Chen, Chuan-Feng; Chemical communications (Cambridge, England) 60 (2024) 4962–4965; doi:10.1039/d4cc00928b

data_7132947
_publ_section_title
;
 A calix[3]carbazole-based cavitand: synthesis, structure and its
 complexation with fullerenes.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4962
_journal_page_last               4965
_journal_paper_doi               10.1039/d4cc00928b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '2(C6 H4 Cl2), C81 H39 N9 O6, C60'
_chemical_formula_sum            'C153 H47 Cl4 N9 O6'
_chemical_formula_weight         2248.79
_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
_audit_creation_date             2023-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-04 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.916(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0791(4)
_cell_length_b                   32.0488(9)
_cell_length_c                   27.0224(9)
_cell_measurement_reflns_used    12160
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      70.7360
_cell_measurement_theta_min      2.1510
_cell_volume                     11285.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(10)
_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 0.953
_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    -24.00  19.00   0.50    5.00    --  -47.09  20.00-127.00   86
  2  \w   -115.00 -56.00   0.50    5.00    --  -47.09 -20.00  65.00  118
  3  \w    -22.00   3.00   0.50    5.00    --   47.09 -20.00  65.00   50
  4  \w     38.00 122.00   0.50    5.00    --   47.09  20.00-127.00  168
  5  \w    111.00 177.00   0.50    6.00    --  103.25  20.00-127.00  132
  6  \w   -133.00 -94.00   0.50    6.00    -- -104.50 -20.00  65.00   78
  7  \w    -38.00  24.00   0.50    5.00    --  -47.09  38.00   0.00  124
  8  \w     39.00  93.00   0.50    5.00    --   47.09-125.00-120.00  108
  9  \w     37.00  73.00   0.50    6.00    --  103.25 -61.00 120.00   72
 10  \w     39.00 106.00   0.50    6.00    --  103.25 -94.00 -90.00  134
 11  \w     45.00  75.00   0.50    6.00    --  103.25 -61.00 150.00   60
 12  \w     92.00 178.00   0.50    6.00    --  103.25  30.00 -90.00  172
 13  \w     32.00  71.00   0.50    6.00    --  103.25 -61.00 -30.00   78
 14  \w     38.00  74.00   0.50    6.00    --  103.25 -61.00-120.00   72
 15  \w     31.00  74.00   0.50    6.00    --  103.25 -61.00   0.00   86
 16  \w     64.00 105.00   0.50    6.00    --  103.25 -94.00-120.00   82
 17  \w     36.00  74.00   0.50    6.00    --  103.25 -61.00 -90.00   76
 18  \w     46.00 106.00   0.50    6.00    --  103.25 -94.00 -30.00  120
 19  \w     31.00  63.00   0.50    6.00    --  103.25 -61.00 -60.00   64
 20  \w    -66.00 -37.00   0.50    6.00    -- -104.50  61.00  30.00   58
 21  \w   -167.00 -93.00   0.50    6.00    -- -104.50 -30.00-150.00  148
 22  \w   -173.00-110.50   0.50    6.00    -- -104.50 -30.00 150.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1143955000
_diffrn_orient_matrix_UB_12      -0.0112382000
_diffrn_orient_matrix_UB_13      0.0102339000
_diffrn_orient_matrix_UB_21      -0.0078301000
_diffrn_orient_matrix_UB_22      0.0063170000
_diffrn_orient_matrix_UB_23      0.0560863000
_diffrn_orient_matrix_UB_31      -0.0287221000
_diffrn_orient_matrix_UB_32      -0.0463105000
_diffrn_orient_matrix_UB_33      0.0051986000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            80169
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.273
_diffrn_reflns_theta_min         2.143
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.493
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       plate
_exptl_crystal_F_000             4576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         2.068
_refine_diff_density_min         -1.084
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       0.00056(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.512
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1550
_refine_ls_number_reflns         22551
_refine_ls_number_restraints     633
_refine_ls_restrained_S_all      1.539
_refine_ls_R_factor_all          0.1961
_refine_ls_R_factor_gt           0.1425
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4056
_refine_ls_wR_factor_ref         0.4366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13163
_reflns_number_total             22551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00928b2.cif
_cod_data_source_block           tx12791_auto
_cod_depositor_comments
'Adding full bibliography for 7132945--7132948.cif.'
_cod_database_code               7132947
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl'
_chemical_oxdiff_usercomment     ' C H N O Cl'
_diffrn_oxdiff_digest_frames
;
010565cdc34a1b7510823d680a55c49e49000262ee7
;
_diffrn_oxdiff_digest_hkl
;
019e72493cc4758a3ccf5e933f9f435199406d
;
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C32-C27 = C27-C28 = C29-C28 = C29-C30 = C30-C31 = C32-C31 = C55-C34 = C34-C35
 = C35-C58 = C57-C56 = C57-C58 = C59-C58 = C57-C46 = C45-C46 = C45-C44 = C44-
 C59 = C43-C44 = C3-C43 = C3-C2 = C3-C4 = C4-C12 = C4-C5 = C13-C12 = C13-C42 =
 C42-C43 = C48-C49 = C50-C49 = C50-C51 = C50-C53 = C27-C26 = C32-C33 = C34-C33 =
  C39-C37 = C40-C41 = C40-C39 = C39-C24 = C40-C14 = C17-C18 = C17-C22 = C17-C16
 = C15-C16 = C23-C15 = C49-C7 = C8-C7 = C8-C52 = C9-C18 = C19-C18
 1.39 with sigma of 0.01
 C80-C3X = C80-C136 = C77-C3X = C77-C4H = C75-C4H = C75-C136
 1.39 with sigma of 0.01
3. Rigid bond restraints
 C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C18, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C35, C58
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C27, C28
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C31, C32
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C37, C39
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C46, C57
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C53, C54
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C50, C51
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C40, C41
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57
\\sim C58 \\sim C59 \\sim C60: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(C4H) \\sim Ueq, Uanis(C75) \\sim Ueq, Uanis(C136) \\sim Ueq, Uanis(C80)
\\sim Ueq, Uanis(C3X) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C1K(H1KA,H1KB), C1X(H1XA,H1XB), C89(H89A,H89B)
5.b Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1C(H1C), C1D(H1D), C1H(H1H), C1S(H1S), C2A(H2A), C2D(H2D),
 C2F(H2F), C2K(H2K), C2M(H2M), C2Q(H2Q), C2R(H2R), C2U(H2U), C2V(H2V),
 C3AA(H3AA), C3E(H3E), C3Z(H3Z), C4AA(H4AA), C4C(H4C), C4G(H4G), C4H(H4H),
 C4P(H4P), C4T(H4T), C4W(H4W), C63(H63), C64(H64), C65(H65), C67(H67), C69(H69),
  C71(H71), C73(H73), C75(H75), C76(H76), C79(H79), C80(H80), C81(H81),
 C82(H82), C84(H84), C87(H87), C90(H90), C136(H136)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              49373
_shelx_hkl_checksum              34625
_shelx_fab_checksum              4437
_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 2.192
_oxdiff_exptl_absorpt_empirical_full_min 0.552