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_7132948
_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, C70'
_chemical_formula_sum            'C163 H47 Cl4 N9 O6'
_chemical_formula_weight         2368.89
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-04 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.007(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.5926(7)
_cell_length_b                   32.9430(7)
_cell_length_c                   30.1206(12)
_cell_measurement_reflns_used    18392
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.0360
_cell_measurement_theta_min      2.2300
_cell_volume                     24288.0(15)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.959
_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   -114.00 -36.00   0.50    7.00    --  -47.09 -33.00 114.00  156
  2  \w    -17.00  17.00   0.50    7.00    --  -47.09  33.00 -86.00   68
  3  \w     38.00 120.00   0.50    7.00    --   47.09  33.00 -86.00  164
  4  \w     -5.00  27.00   0.50    7.00    --   47.09 -33.00 114.00   64
  5  \w     90.00 177.00   0.50   15.00    --  103.25  33.00 -86.00  174
  6  \w   -156.00-131.00   0.50   15.00    -- -104.50 -33.00 114.00   50
  7  \w     -5.00  20.00   0.50    7.00    --  -47.09  19.00  60.00   50
  8  \w    -39.00  25.00   0.50    7.00    --  -47.09  38.00  60.00  128
  9  \w     54.00  81.00   0.50    7.00    --   47.09-125.00-120.00   54
 10  \w    127.00 161.00   0.50   15.00    --  103.25  30.00-150.00   68
 11  \w     33.00  75.00   0.50   15.00    --  103.25 -61.00 150.00   84
 12  \w     79.00 108.00   0.50   15.00    --  103.25 -77.00-150.00   58
 13  \w     36.00  68.00   0.50   15.00    --  103.25 -61.00 -60.00   64
 14  \w     42.00  69.00   0.50   15.00    --  103.25 -61.00 -90.00   54
 15  \w     35.00  73.00   0.50   15.00    --  103.25 -61.00  90.00   76
 16  \w     45.00  72.00   0.50   15.00    --  103.25 -61.00  60.00   54
 17  \w     43.00  70.00   0.50   15.00    --  103.25 -61.00   0.00   54
 18  \w     31.00  66.00   0.50   15.00    --  103.25 -61.00 120.00   70
 19  \w     41.00 106.00   0.50   15.00    --  103.25-125.00  30.00  130
 20  \w     31.00  96.00   0.50   15.00    --  103.25 -94.00 -60.00  130
 21  \w     41.00 103.00   0.50   15.00    --  103.25 -77.00   0.00  124
 22  \w     98.00 125.00   0.50   15.00    --  103.25  30.00-150.00   54
 23  \w    -63.00 -33.00   0.50   15.00    -- -104.50  61.00-120.00   60
 24  \w   -170.00 -91.00   0.50   15.00    -- -104.50 -15.00   0.00  158
 25  \w    -66.00 -36.00   0.50   15.00    -- -104.50  61.00 -90.00   60
 26  \w    -67.00 -33.00   0.50   15.00    -- -104.50  61.00 -60.00   68
;
_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      -0.0562790000
_diffrn_orient_matrix_UB_12      0.0192965000
_diffrn_orient_matrix_UB_13      -0.0103974000
_diffrn_orient_matrix_UB_21      0.0149241000
_diffrn_orient_matrix_UB_22      0.0048410000
_diffrn_orient_matrix_UB_23      0.0545443000
_diffrn_orient_matrix_UB_31      0.0239239000
_diffrn_orient_matrix_UB_32      0.0423148000
_diffrn_orient_matrix_UB_33      -0.0014731000
_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  0.1184
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            175708
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.046
_diffrn_reflns_theta_min         2.249
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27555
_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    1.296
_exptl_crystal_description       plate
_exptl_crystal_F_000             9632
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.395
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3277
_refine_ls_number_reflns         48649
_refine_ls_number_restraints     1187
_refine_ls_restrained_S_all      1.443
_refine_ls_R_factor_all          0.2002
_refine_ls_R_factor_gt           0.1108
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2615
_refine_ls_wR_factor_ref         0.2962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22574
_reflns_number_total             48649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00928b2.cif
_cod_data_source_block           tx12953_auto_sq
_cod_depositor_comments
'Adding full bibliography for 7132945--7132948.cif.'
_cod_original_cell_volume        24288.0(14)
_cod_database_code               7132948
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOCl
_chemical_oxdiff_usercomment     CHNOCl
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C166-C165 = C165-C164 = C169-C164 = C169-C168 = C168-C167 = C167-C166
 1.39 with sigma of 0.01
 C96A-C83A = C97A-C1E = C97A-C96A = C84A-C83A = C84A-C1E = C98A-C97A = C99A-
 C98A = C91A-C90A = C1L-C1C = C1T-C1C = C1T-C1F = C1Y-C1F = C2C-C1Y = C2C-C1L =
 C2L-C1N = C2X-C2L = C2D-C1O = C2D-C1Z = C2X-C1O = C1Z-C1N
 1.39 with sigma of 0.01
 C87A-C82A = C87A-C86A = C86A-C85A = C1X-C1Q = C1R-C1Q = C89A-C2W
 1.39 with sigma of 0.01
3. Rigid bond restraints
 C172, C173
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3C, C2G
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C130, C129
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C166 \\sim C165 \\sim C164 \\sim C169 \\sim C168 \\sim C167 \\sim Cl5 \\sim
Cl6: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
1.7A
C2Y \\sim C1B \\sim C2R \\sim C3C \\sim C98A \\sim C1G \\sim C1J \\sim C2G
\\sim C95A \\sim C97A \\sim C99A \\sim C2U \\sim C2I \\sim C3B \\sim C1H \\sim
C94A \\sim C96A \\sim C1E \\sim C2K \\sim C1D \\sim C1I \\sim C2S \\sim C1O
\\sim C2X \\sim C93A \\sim C91A \\sim C83A \\sim C84A \\sim C2V \\sim C2P \\sim
C2H \\sim C2D \\sim C2Q \\sim C2L \\sim C92A \\sim C82A \\sim C90A \\sim C1U
\\sim C85A \\sim C1S \\sim C2Z \\sim C1M \\sim C2B \\sim C1Z \\sim C1P \\sim
C1N \\sim C2J \\sim C87A \\sim C89A \\sim C2E \\sim C86A \\sim C2T \\sim C1C
\\sim C1L \\sim C1K \\sim C2O \\sim C2F \\sim C88A \\sim C2W \\sim C2M \\sim
C2N \\sim C1Y \\sim C2C \\sim C1T \\sim C1V \\sim C1Q \\sim C1X \\sim C1R \\sim
C1F \\sim C1W: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 1.7A
C172 \\sim C173 \\sim C171 \\sim C170 \\sim C175 \\sim C174: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
Uanis(C167) \\sim Ueq, Uanis(C166) \\sim Ueq, Uanis(C165) \\sim Ueq,
Uanis(C164) \\sim Ueq, Uanis(C168) \\sim Ueq, Uanis(C169) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C2K) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C2R) \\sim Ueq, Uanis(C3C)
\\sim Ueq, Uanis(C98A) \\sim Ueq, Uanis(C1G) \\sim Ueq, Uanis(C1J) \\sim Ueq,
Uanis(C2G) \\sim Ueq, Uanis(C95A) \\sim Ueq, Uanis(C97A) \\sim Ueq, Uanis(C99A)
\\sim Ueq, Uanis(C2U) \\sim Ueq, Uanis(C2I) \\sim Ueq, Uanis(C3B) \\sim Ueq,
Uanis(C1H) \\sim Ueq, Uanis(C94A) \\sim Ueq, Uanis(C96A) \\sim Ueq, Uanis(C1E)
\\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(C1I) \\sim Ueq, Uanis(C2S) \\sim Ueq,
Uanis(C1O) \\sim Ueq, Uanis(C2X) \\sim Ueq, Uanis(C93A) \\sim Ueq, Uanis(C91A)
\\sim Ueq, Uanis(C83A) \\sim Ueq, Uanis(C2Y) \\sim Ueq, Uanis(C84A) \\sim Ueq,
Uanis(C2V) \\sim Ueq, Uanis(C2P) \\sim Ueq, Uanis(C2H) \\sim Ueq, Uanis(C2D)
\\sim Ueq, Uanis(C2Q) \\sim Ueq, Uanis(C2L) \\sim Ueq, Uanis(C92A) \\sim Ueq,
Uanis(C82A) \\sim Ueq, Uanis(C90A) \\sim Ueq, Uanis(C1U) \\sim Ueq, Uanis(C85A)
\\sim Ueq, Uanis(C1S) \\sim Ueq, Uanis(C2Z) \\sim Ueq, Uanis(C1M) \\sim Ueq,
Uanis(C2B) \\sim Ueq, Uanis(C1Z) \\sim Ueq, Uanis(C1P) \\sim Ueq, Uanis(C1N)
\\sim Ueq, Uanis(C2J) \\sim Ueq, Uanis(C87A) \\sim Ueq, Uanis(C89A) \\sim Ueq,
Uanis(C2E) \\sim Ueq, Uanis(C86A) \\sim Ueq, Uanis(C2T) \\sim Ueq, Uanis(C1C)
\\sim Ueq, Uanis(C1L) \\sim Ueq, Uanis(C1K) \\sim Ueq, Uanis(C2O) \\sim Ueq,
Uanis(C2F) \\sim Ueq, Uanis(C88A) \\sim Ueq, Uanis(C2W) \\sim Ueq, Uanis(C2M)
\\sim Ueq, Uanis(C2N) \\sim Ueq, Uanis(C1Y) \\sim Ueq, Uanis(C2C) \\sim Ueq,
Uanis(C1T) \\sim Ueq, Uanis(C1V) \\sim Ueq, Uanis(C1Q) \\sim Ueq, Uanis(C1X)
\\sim Ueq, Uanis(C1R) \\sim Ueq, Uanis(C1F) \\sim Ueq, Uanis(C1W) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C28(H28A,H28B), C55(H55A,H55B), C1A(H1AA,H1AB), C28A(H28C,H28D),
 C55A(H55C,H55D)
5.b Aromatic/amide H refined with riding coordinates:
 C153(H153), C154(H154), C155(H155), C156(H156), C159(H159), C160(H160),
 C161(H161), C162(H162), C165(H165), C166(H166), C167(H167), C168(H168),
 C171(H171), C172(H172), C173(H173), C174(H174), C3(H3), C6(H6), C12(H12),
 C15(H15), C18(H18), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C31(H31), C34(H34), C39(H39), C42(H42), C45(H45), C48(H48), C50(H50),
 C51(H51), C52(H52), C53(H53), C54(H54), C58(H58), C61(H61), C66(H66), C69(H69),
  C72(H72), C75(H75), C77(H77), C78(H78), C79(H79), C80(H80), C81(H81),
 C3A(H3A), C6A(H6A), C12A(H12A), C15A(H15A), C18A(H18A), C21A(H21A), C23A(H23A),
  C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A), C31A(H31A), C34A(H34A),
 C39A(H39A), C42A(H42A), C45A(H45A), C48A(H48A), C50A(H50A), C51A(H51A),
 C52A(H52A), C53A(H53A), C54A(H54A), C58A(H58A), C61A(H61A), C66A(H66A),
 C69A(H69A), C72A(H72A), C75A(H75A), C77A(H77A), C78A(H78A), C79A(H79A),
 C80A(H80A), C81A(H81A)
;
_shelx_res_checksum              79123
_shelx_hkl_checksum              34180
_shelx_fab_checksum              59826
_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 1.872
_oxdiff_exptl_absorpt_empirical_full_min 0.598