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_1565861
_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, C3 H6 O2'
_chemical_formula_sum            'C69 H90 O8'
_chemical_formula_weight         1047.40
_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             2020-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.288(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0366(3)
_cell_length_b                   18.4996(3)
_cell_length_c                   19.7620(3)
_cell_measurement_reflns_used    8969
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      68.9140
_cell_measurement_theta_min      3.2490
_cell_volume                     6210.96(18)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_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   -124.00 -73.00   1.00   13.72    --  -35.25-125.00 -30.00   51
  2  \w   -124.00 -73.00   1.00   13.72    --  -35.25-125.00-120.00   51
  3  \w    -96.00  -2.00   1.00   13.72    --  -35.25 125.00 150.00   94
  4  \w     23.00 100.00   1.00   13.72    --   35.25-125.00-150.00   77
  5  \w      1.00  85.00   1.00   13.72    --   35.25 -99.00  60.00   84
  6  \w     -5.00 125.00   1.00   13.72    --   35.25  57.00 -60.00  130
  7  \w    -54.00  81.00   1.00   13.72    --   35.25 -37.00-180.00  135
  8  \w    100.00 178.00   1.00   35.00    --  103.90 111.00 120.00   78
  9  \w    100.00 178.00   1.00   35.00    --  103.90 111.00   0.00   78
 10  \w     63.00 178.00   1.00   35.00    --  103.90  50.00-120.00  115
 11  \w     63.00 178.00   1.00   35.00    --  103.90  50.00-180.00  115
 12  \w     12.00 146.00   1.00   35.00    --  103.90 -63.00  90.00  134
 13  \w    100.00 178.00   1.00   35.00    --  103.90 111.00  90.00   78
 14  \w     59.00 178.00   1.00   35.00    --  103.90  37.00 -60.00  119
 15  \w    100.00 150.00   1.00   35.00    --  103.90 111.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0110489000
_diffrn_orient_matrix_UB_12      0.0669828000
_diffrn_orient_matrix_UB_13      -0.0446482000
_diffrn_orient_matrix_UB_21      -0.0809756000
_diffrn_orient_matrix_UB_22      -0.0139765000
_diffrn_orient_matrix_UB_23      -0.0378271000
_diffrn_orient_matrix_UB_31      -0.0392809000
_diffrn_orient_matrix_UB_32      0.0475378000
_diffrn_orient_matrix_UB_33      0.0517883000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35347
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.047
_diffrn_reflns_theta_min         3.277
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88047
_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    1.120
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     825
_refine_ls_number_reflns         11386
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0827
_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^)+(0.1311P)^2^+5.3256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2231
_refine_ls_wR_factor_ref         0.2383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8785
_reflns_number_total             11386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5024.cif
_cod_data_source_block           x6_methyl_acetate
_cod_database_code               1565861
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C60 H60 O20'
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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
 C62-C63A \\sim C62-C63B
 with sigma of 0.02
 C62-C64A \\sim C62-C64B
 with sigma of 0.02
 C62-C65A \\sim C62-C65B
 with sigma of 0.02
 O7-O8 \\sim O7A-O8A
 with sigma of 0.04
 O7-C70 \\sim O7A-C70A
 with sigma of 0.04
 O7-C73 \\sim O7A-C73A
 with sigma of 0.04
 O8-C70 \\sim O8A-C70A
 with sigma of 0.04
 O8-C72 \\sim O8A-C72A
 with sigma of 0.04
 O8-C73 \\sim O8A-C73A
 with sigma of 0.04
 C70-C72 \\sim C70A-C72A
 with sigma of 0.04
 C70-C73 \\sim C70A-C73A
 with sigma of 0.04
 C18-C21 \\sim C18-C20A
 with sigma of 0.02
 C18-C20 \\sim C18-C19A
 with sigma of 0.02
 C18-C19 \\sim C18-C21A
 with sigma of 0.02
3. Restrained planarity
 C73A, C70A, O7A, O8A
 with sigma of 0.1
 O8, C70, O7, C73
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C65A) = Uanis(C63B)
Uanis(C63A) = Uanis(C64B)
Uanis(C64A) = Uanis(C65B)
Uanis(O7A) = Uanis(C70A) = Uanis(O8A)
Uanis(C21A) = Uanis(C21)
5. Others
 Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=
 Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(H43C)=1-FVAR(1)
 Sof(C41A)=Sof(H41D)=Sof(H41E)=Sof(H41F)=Sof(C42A)=Sof(H42D)=Sof(H42E)=
 Sof(H42F)=Sof(C43A)=Sof(H43D)=Sof(H43E)=Sof(H43F)=FVAR(1)
 Sof(C63B)=Sof(H63D)=Sof(H63E)=Sof(H63F)=Sof(C64B)=Sof(H64D)=Sof(H64E)=
 Sof(H64F)=Sof(C65B)=Sof(H65D)=Sof(H65E)=Sof(H65F)=1-FVAR(2)
 Sof(C63A)=Sof(H63A)=Sof(H63B)=Sof(H63C)=Sof(C64A)=Sof(H64A)=Sof(H64B)=
 Sof(H64C)=Sof(C65A)=Sof(H65A)=Sof(H65B)=Sof(H65C)=FVAR(2)
 Sof(O8A)=Sof(O7A)=Sof(C70A)=Sof(C73A)=Sof(H73D)=Sof(H73E)=Sof(H73F)=Sof(C72A)=
 Sof(H72D)=Sof(H72E)=Sof(H72F)=1-FVAR(3)
 Sof(O7)=Sof(O8)=Sof(C70)=Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(H72C)=Sof(C73)=
 Sof(H73A)=Sof(H73B)=Sof(H73C)=FVAR(3)
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(4)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(4)
6.a 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.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5A), C13(H13), C15(H15), C26(H26), C28(H28), C35(H35), C37(H37),
 C48(H48), C50(H50), C57(H57), C59(H59)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C30(H30A,H30B,H30C),
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C41(H41A,H41B,H41C), C42(H42A,H42B,
 H42C), C43(H43A,H43B,H43C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,
 H54B,H54C), C41A(H41D,H41E,H41F), C42A(H42D,H42E,H42F), C43A(H43D,H43E,H43F),
 C63A(H63A,H63B,H63C), C64A(H64A,H64B,H64C), C65A(H65A,H65B,H65C), C63B(H63D,
 H63E,H63F), C64B(H64D,H64E,H64F), C65B(H65D,H65E,H65F), C72(H72A,H72B,H72C),
 C73(H73A,H73B,H73C), C73A(H73D,H73E,H73F), C72A(H72D,H72E,H72F), C21(H21A,H21B,
 H21C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C21A(H21D,H21E,H21F),
 C19A(H19D,H19E,H19F), C20A(H20D,H20E,H20F)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6)
;
_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 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.612