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_1565853
_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 H16'
_chemical_formula_sum            'C73 H100 O6'
_chemical_formula_weight         1073.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 101.773(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2520(5)
_cell_length_b                   23.5373(7)
_cell_length_c                   17.2102(4)
_cell_measurement_reflns_used    7499
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8870
_cell_measurement_theta_min      3.1890
_cell_volume                     6444.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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 -13.00   1.00   15.00    --  -41.41 -57.00 -30.00  101
  2  \w    -66.00  33.00   1.00   15.00    --  -41.41  37.00 120.00   99
  3  \w    -66.00  33.00   1.00   15.00    --  -41.41  37.00-120.00   99
  4  \w     30.00 139.00   1.00   50.00    --  106.16 -77.00 -30.00  109
  5  \w    101.00 178.00   1.00   50.00    --  106.16  96.00  75.00   77
  6  \w     30.00 134.00   1.00   50.00    --  106.16 -30.00 -30.00  104
  7  \w     94.00 178.00   1.00   50.00    --  106.16 125.00   0.00   84
  8  \w     94.00 178.00   1.00   50.00    --  106.16 125.00 -90.00   84
  9  \w     74.00 178.00   1.00   50.00    --  106.16  77.00 120.00  104
 10  \w     77.00 155.00   1.00   50.00    --  106.16  61.00-180.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0271416000
_diffrn_orient_matrix_UB_12      0.0570434000
_diffrn_orient_matrix_UB_13      0.0411386000
_diffrn_orient_matrix_UB_21      -0.0910450000
_diffrn_orient_matrix_UB_22      0.0219521000
_diffrn_orient_matrix_UB_23      -0.0238030000
_diffrn_orient_matrix_UB_31      -0.0188603000
_diffrn_orient_matrix_UB_32      -0.0234119000
_diffrn_orient_matrix_UB_33      0.0780932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37071
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.114
_diffrn_reflns_theta_min         3.226
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.106
_exptl_crystal_description       plate
_exptl_crystal_F_000             2344
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     804
_refine_ls_number_reflns         12820
_refine_ls_number_restraints     82
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0655
_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^)+(0.1019P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.2070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6910
_reflns_number_total             12820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5024.cif
_cod_data_source_block           x6_heptane_10
_cod_database_code               1565853
_chemical_oxdiff_usercomment     '100 K, colourless plate'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.886
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C7-C10 = C7-C8 = C7-C9 = C7-C4
 1.54 with sigma of 0.02
 C51-C54 = C51-C52A = C51-C53A = C51-C47 = C51-C53 = C51-C52 = C51-C54A
 1.54 with sigma of 0.005
 C69-C70 = C69-C68
 1.54 with sigma of 0.005
 C71-C70 = C71-C72
 1.54 with sigma of 0.005
 C18-C14
 1.54 with sigma of 0.02
 C70-C69 = C70-C71
 1.54 with sigma of 0.005
 C72-C71 = C72-C73
 1.54 with sigma of 0.005
 C68-C69 = C68-C67
 1.54 with sigma of 0.005
 C7-C8A = C7-C8 = C7-C9 = C7-C10 = C7-C4 = C7-C9A = C7-C10A
 1.54 with sigma of 0.02
 C18A-C14 = C18A-C21A = C18A-C20A = C18A-C19A
 1.54 with sigma of 0.02
 C18-C14 = C18-C20B = C18-C21B = C18-C19B
 1.54 with sigma of 0.02
 C20B-C14
 2.51 with sigma of 0.04
 C8-C10
 2.51 with sigma of 0.01
 C9-C10
 2.51 with sigma of 0.04
 C20A-C19A
 2.51 with sigma of 0.04
 C19A-C21A
 2.51 with sigma of 0.04
 C9-C8
 2.51 with sigma of 0.04
 C10-C4
 2.51 with sigma of 0.04
 C8-C4
 2.51 with sigma of 0.04
 C14-C19A
 2.51 with sigma of 0.04
 C14-C21B
 2.51 with sigma of 0.04
 C20B-C21B
 2.51 with sigma of 0.04
 C20A-C21A
 2.51 with sigma of 0.04
 C20B-C19B
 2.51 with sigma of 0.04
 C14-C20A
 2.51 with sigma of 0.04
 C19B-C21B
 2.51 with sigma of 0.04
 C14-C21A
 2.51 with sigma of 0.04
 C14-C19B
 2.51 with sigma of 0.04
 C10A-C4
 2.51 with sigma of 0.04
 C9A-C10A
 2.51 with sigma of 0.04
 C9A-C4
 2.51 with sigma of 0.04
 C9-C4
 2.51 with sigma of 0.04
 C8A-C9A
 2.51 with sigma of 0.04
 C10A-C8A
 2.51 with sigma of 0.04
 C8A-C4
 2.51 with sigma of 0.04
 C51-C52 \\sim C51-C52A
 with sigma of 0.02
 C51-C53 \\sim C51-C53A
 with sigma of 0.02
3. Rigid bond restraints
 C52, C51
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C52 \\sim C51: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C54) \\sim Ueq, Uanis(C52A) \\sim Ueq: with sigma of 0.0001 and sigma for
terminal atoms of 0.002
Uanis(C54) = Uanis(C54A)
Uanis(C52A) = Uanis(C52)
Uanis(C10A) = Uanis(C10)
Uanis(C8A) = Uanis(C8)
Uanis(C9) = Uanis(C9A)
Uanis(C53) = Uanis(C53A)
5. Others
 Sof(C18)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21B)=Sof(H21D)=
 Sof(H21E)=Sof(H21F)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(1)
 Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C20A)=Sof(H20A)=Sof(H20B)=
 Sof(H20C)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C18A)=FVAR(1)
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=
 Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(2)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(2)
 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(3)
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=
 Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C55(H55A,H55B), C22(H22A,H22B), C66(H66A,H66B), C11(H11A,
 H11B), C44(H44A,H44B), C69(H69A,H69B), C71(H71A,H71B), C70(H70A,H70B),
 C72(H72A,H72B), C68(H68A,H68B)
6.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C26(H26), C13(H13), C3(H3A), C5(H5), C37(H37), C48(H48), C15(H15),
 C35(H35), C57(H57), C59(H59), C46(H46)
6.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C42(H42A,H42B,H42C), C32(H32A,H32B,H32C), C43(H43A,H43B,
 H43C), C41(H41A,H41B,H41C), C65(H65A,H65B,H65C), C54(H54A,H54B,H54C), C64(H64A,
 H64B,H64C), C31(H31A,H31B,H31C), C63(H63A,H63B,H63C), C53(H53A,H53B,H53C),
 C52(H52A,H52B,H52C), C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C73(H73A,H73B,H73C),
  C67(H67A,H67B,H67C), C9(H9A,H9B,H9C), C21A(H21A,H21B,H21C), C20A(H20A,H20B,
 H20C), C19A(H19A,H19B,H19C), C20B(H20D,H20E,H20F), C21B(H21D,H21E,H21F),
 C19B(H19D,H19E,H19F), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C10A(H10D,H10E,
 H10F), C52A(H52D,H52E,H52F), C54A(H54D,H54E,H54F), C53A(H53D,H53E,H53F)
6.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O6(H6), O4(H4), O1(H1), O5(H5A)
;
_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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.535