Insights into molecular recognition from the crystal structures of <i>p-tert</i>-butylcalix[6]arene complexed with different solvents
Malinska, Maura; IUCrJ 9 (2022) 55–64; doi:10.1107/S2052252521010678

data_1565863
_publ_section_title
;
 Insights into molecular recognition from the crystal structures of
 <i>p-tert</i>-butylcalix[6]arene complexed with different solvents
;
_journal_coeditor_code           ED5024
_journal_issue                   1
_journal_name_full               IUCrJ
_journal_page_first              55
_journal_page_last               64
_journal_paper_doi               10.1107/S2052252521010678
_journal_volume                  9
_journal_year                    2022
_chemical_formula_moiety         'C66 H84 O6, C7 H8 O'
_chemical_formula_sum            'C73 H92 O7'
_chemical_formula_weight         1081.46
_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
_cell_angle_alpha                83.979(5)
_cell_angle_beta                 72.392(5)
_cell_angle_gamma                73.292(5)
_cell_formula_units_Z            2
_cell_length_a                   14.1349(8)
_cell_length_b                   16.1763(11)
_cell_length_c                   17.0355(10)
_cell_measurement_reflns_used    8585
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.0680
_cell_measurement_theta_min      1.8390
_cell_volume                     3555.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.4441
_diffrn_detector_type            Opal
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -90.00 -32.00   1.00   22.50    --   -0.70 179.00 150.00   58
  2  \w     34.00 117.00   1.00   30.00    --   26.29 179.00 -90.00   83
  3  \w    -21.00 105.00   1.00   30.00    --   26.29  38.00   0.00  126
  4  \w     34.00 117.00   1.00   30.00    --   26.29 179.00-180.00   83
  5  \w    -24.00  25.00   1.00   30.00    --  -27.70-100.00 -60.00   49
  6  \w   -107.00  20.00   1.00   30.00    --  -27.70 -38.00  60.00  127
  7  \w   -102.00   5.00   1.00   30.00    --  -27.70 -57.00 -30.00  107
  8  \w   -108.00  13.00   1.00   30.00    --  -27.70 -78.00-120.00  121
  9  \w     32.00  89.00   1.00   22.50    --   -0.70-179.00   0.00   57
 10  \w    -48.00  59.00   1.00   30.00    --   26.29 -57.00-150.00  107
 11  \w     34.00 117.00   1.00   30.00    --   26.29 179.00  60.00   83
 12  \w    -48.00  50.00   1.00   30.00    --   26.29 -57.00 -30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Opal'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454896000
_diffrn_orient_matrix_UB_12      -0.0050276000
_diffrn_orient_matrix_UB_13      0.0299357000
_diffrn_orient_matrix_UB_21      -0.0182664000
_diffrn_orient_matrix_UB_22      0.0454081000
_diffrn_orient_matrix_UB_23      0.0045911000
_diffrn_orient_matrix_UB_31      -0.0242158000
_diffrn_orient_matrix_UB_32      0.0030885000
_diffrn_orient_matrix_UB_33      -0.0314918000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_unetI/netI     0.1178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49801
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.755
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.010
_exptl_crystal_description       block
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.134
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     762
_refine_ls_number_reflns         13019
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.360
_refine_ls_R_factor_all          0.2133
_refine_ls_R_factor_gt           0.1429
_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          0.3812
_refine_ls_wR_factor_ref         0.4373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6833
_reflns_number_total             13019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5024.cif
_cod_data_source_block           9_x6_anisole
_cod_database_code               1565863
_chemical_oxdiff_formula         'C60 H48 O6 N1'
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 C30-C29
 1.529 with sigma of 0.02
 C30A-C29
 1.529 with sigma of 0.02
 C40-C38 = C40-C41A = C40-C42A = C40-C43A = C40-C41 = C40-C42 = C40-C43
 1.53 with sigma of 0.01
 C18-C19A = C18-C20A = C18-C21A = C18-C19 = C18-C20 = C18-C21 = C18-C16
 1.53 with sigma of 0.01
 C7-C4 = C7-C8A = C7-C9A = C7-C10A
 1.53 with sigma of 0.02
 C29-C27 = C29-C30 = C29-C31 = C29-C32 = C29-C30A = C29-C31A = C29-C32A
 1.53 with sigma of 0.02
 C62-C60 = C62-C63 = C62-C64 = C62-C65
 1.53 with sigma of 0.02
 C51-C49 = C51-C52 = C51-C53 = C51-C54
 1.53 with sigma of 0.02
 C51-C49 = C51-C52 = C51-C53 = C51-C54 = C51-C52A = C51-C54A = C51-C53A
 1.53 with sigma of 0.02
 O7A-C67A
 1.42 with sigma of 0.02
 C71-O7A
 1.37 with sigma of 0.02
 C31A-C30A
 2.5 with sigma of 0.04
 C27-C31
 2.51 with sigma of 0.04
 C30-C32
 2.51 with sigma of 0.04
 C30-C31
 2.51 with sigma of 0.04
 C27-C30
 2.51 with sigma of 0.04
 C27-C32
 2.51 with sigma of 0.04
 C32-C31
 2.51 with sigma of 0.04
 C27-C30A
 2.51 with sigma of 0.04
 C31A-C32A
 2.51 with sigma of 0.04
 C27-C31A
 2.51 with sigma of 0.04
 C27-C32A
 2.51 with sigma of 0.04
 C32A-C30A
 2.51 with sigma of 0.04
 C30A-C31A
 2.51 with sigma of 0.04
 C21-C20
 2.51 with sigma of 0.04
 C19-C21
 2.51 with sigma of 0.04
 C16-C20
 2.51 with sigma of 0.04
 C16-C20A
 2.51 with sigma of 0.04
 C16-C21A
 2.51 with sigma of 0.04
 C20A-C21A
 2.51 with sigma of 0.04
 C16-C21
 2.51 with sigma of 0.04
 C16-C19A
 2.51 with sigma of 0.04
 C16-C19
 2.51 with sigma of 0.04
 C20-C19
 2.51 with sigma of 0.04
 C21A-C19A
 2.51 with sigma of 0.04
 C19A-C20A
 2.51 with sigma of 0.04
 C52A-C53A
 2.51 with sigma of 0.04
 C53-C54
 2.51 with sigma of 0.04
 C54-C52
 2.51 with sigma of 0.04
 C49-C52
 2.51 with sigma of 0.04
 C49-C53A
 2.51 with sigma of 0.04
 C53-C49
 2.51 with sigma of 0.04
 C52-C53
 2.51 with sigma of 0.04
 C52A-C49
 2.51 with sigma of 0.04
 C49-C54A
 2.51 with sigma of 0.04
 C49-C54
 2.51 with sigma of 0.04
 C53A-C54A
 2.51 with sigma of 0.04
 C54A-C52A
 2.51 with sigma of 0.04
 C32-C29 \\sim C32A-C29
 with sigma of 0.02
 C30-C29 \\sim C30A-C29
 with sigma of 0.02
 C31-C29 \\sim C31A-C29
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C54) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C54A)
\\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.00001 and sigma for terminal
atoms of 0.0002
Uanis(C42) = Uanis(C42A)
Uanis(C43) = Uanis(C43A)
Uanis(C72) = Uanis(C68) = Uanis(C67) = Uanis(C73) = Uanis(C69) = Uanis(C70) =
Uanis(C71)
Uanis(O7) = Uanis(C67)
Uanis(C67) = Uanis(C67A)
Uanis(C30A) = Uanis(C32)
Uanis(C31) = Uanis(C32A)
Uanis(C31A) = Uanis(C30)
Uanis(C41A) = Uanis(C41)
Uanis(C52) = Uanis(C52A)
Uanis(C53) = Uanis(C53A)
Uanis(C54) = Uanis(C54A)
4. Rigid body (RIGU) restrains
 C7, C9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C10A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C29, C32A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C29, C31A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O7A, C67A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C51, C53A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C41)=Sof(H41D)=Sof(H41E)=Sof(H41F)=Sof(C42)=Sof(H42D)=Sof(H42E)=Sof(H42F)=
 Sof(C43)=Sof(H43D)=Sof(H43E)=Sof(H43F)=1-FVAR(1)
 Sof(C41A)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C42A)=Sof(H42A)=Sof(H42B)=
 Sof(H42C)=Sof(C43A)=Sof(H43A)=Sof(H43B)=Sof(H43C)=FVAR(1)
 Sof(C19)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C20)=Sof(H20D)=Sof(H20E)=Sof(H20F)=
 Sof(C21)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(2)
 Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20A)=Sof(H20A)=Sof(H20B)=
 Sof(H20C)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(2)
 Sof(H68)=Sof(O7A)=Sof(C67A)=Sof(H67D)=Sof(H67E)=Sof(H67F)=1-FVAR(3)
 Sof(O7)=Sof(H71)=Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(H67C)=FVAR(3)
 Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(C31A)=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=Sof(C32A)=Sof(H32D)=Sof(H32E)=Sof(H32F)=1-FVAR(4)
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=FVAR(4)
 Sof(C52A)=Sof(H52D)=Sof(H52E)=Sof(H52F)=Sof(C54A)=Sof(H54D)=Sof(H54E)=
 Sof(H54F)=Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=1-FVAR(5)
 Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(5)
6.a Free rotating group:
 O7(C68,C69,C70,C71,C72,C73,C67)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C22(H22A,H22B), C33(H33A,H33B), C44(H44A,H44B), C55(H55A,
 H55B), C66(H66A,H66B)
6.c Me refined with riding coordinates:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C30A(H30D,H30E,
 H30F), C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F), C43(H43D,H43E,H43F),
 C67(H67A,H67B,H67C)
6.d Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5A), C15(H15), C17(H17), C26(H26), C28(H28), C37(H37), C39(H39),
 C48(H48), C50(H50), C59(H59), C61(H61), C68(H68), C69(H69), C70(H70), C71(H71),
  C72(H72), C73(H73)
6.e Idealised Me refined as rotating group:
 C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C8A(H8AA,H8AB,
 H8AC), C9A(H9AA,H9AB,H9AC), C10A(H10A,H10B,H10C), C19A(H19A,H19B,H19C),
 C20A(H20A,H20B,H20C), C21A(H21A,H21B,H21C), C41A(H41A,H41B,H41C), C42A(H42A,
 H42B,H42C), C43A(H43A,H43B,H43C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C),
 C54(H54A,H54B,H54C), C19(H19D,H19E,H19F), C20(H20D,H20E,H20F), C21(H21D,H21E,
 H21F), C41(H41D,H41E,H41F), C42(H42D,H42E,H42F), C67A(H67D,H67E,H67F),
 C52A(H52D,H52E,H52F), C54A(H54D,H54E,H54F), C53A(H53D,H53E,H53F)
6.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2017-12-04
_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.908