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_1565859
_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, C6 H12'
_chemical_formula_sum            'C72 H96 O6'
_chemical_formula_weight         1057.48
_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     direct
_cell_angle_alpha                90
_cell_angle_beta                 94.521(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2109(4)
_cell_length_b                   18.2986(4)
_cell_length_c                   19.6172(4)
_cell_measurement_reflns_used    12304
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.0130
_cell_measurement_theta_min      3.3360
_cell_volume                     6158.9(2)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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    -99.00 -34.00   1.00    3.60    --    0.00 178.00 -90.00   65
  2  \w    -42.00  92.00   1.00    3.60    --    0.00  55.00  77.00  134
  3  \w      1.00  51.00   1.00    3.60    --    0.00 -99.00 150.00   50
  4  \w   -151.00 -80.00   1.00   15.00    --  -55.02 -94.00   0.00   71
  5  \w     94.00 146.00   1.00   15.00    --   55.02 125.00-180.00   52
  6  \w     12.00 148.00   1.00   15.00    --   55.02  61.00-150.00  136
  7  \w     -2.00 147.00   1.00   15.00    --   55.02  30.00   0.00  149
  8  \w     94.00 146.00   1.00   15.00    --   55.02 125.00-120.00   52
  9  \w     57.00 150.00   1.00   15.00    --  110.04 178.00 120.00   93
 10  \w     64.00 178.00   1.00   15.00    --  110.04  38.00   0.00  114
 11  \w    100.00 178.00   1.00   15.00    --  110.04 111.00 -60.00   78
 12  \w     16.00 154.00   1.00   15.00    --  110.04 -63.00  60.00  138
 13  \w    100.00 178.00   1.00   15.00    --  110.04 111.00  90.00   78
 14  \w     68.00 178.00   1.00   15.00    --  110.04  50.00-120.00  110
 15  \w     18.00 115.00   1.00   15.00    --  110.04-111.00  90.00   97
 16  \w      1.00  51.00   1.00    3.60    --    0.00 -99.00 -60.00   50
 17  \w    -42.00  92.00   1.00    3.60    --    0.00  57.00-150.00  134
 18  \w   -151.00 -80.00   1.00   15.00    --  -55.02 -94.00-150.00   71
 19  \w     12.00 148.00   1.00   15.00    --   55.02  61.00  90.00  136
 20  \w     94.00 146.00   1.00   15.00    --   55.02 125.00 -30.00   52
 21  \w     12.00 148.00   1.00   15.00    --   55.02  61.00  30.00  136
 22  \w     94.00 146.00   1.00   15.00    --   55.02 125.00  30.00   52
 23  \w     12.00 148.00   1.00   15.00    --   55.02  61.00 150.00  136
 24  \w    100.00 110.00   1.00   15.00    --  110.04 111.00   0.00   10
;
_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      0.0219708000
_diffrn_orient_matrix_UB_12      0.0614623000
_diffrn_orient_matrix_UB_13      0.0516909000
_diffrn_orient_matrix_UB_21      0.0854656000
_diffrn_orient_matrix_UB_22      -0.0258292000
_diffrn_orient_matrix_UB_23      0.0048233000
_diffrn_orient_matrix_UB_31      0.0166046000
_diffrn_orient_matrix_UB_32      0.0514839000
_diffrn_orient_matrix_UB_33      -0.0592006000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19018
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.723
_diffrn_reflns_theta_min         3.290
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66942
_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    1.140
_exptl_crystal_description       prism
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     803
_refine_ls_number_reflns         19018
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0652
_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^)+(0.1038P)^2^+1.0348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.1971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11945
_reflns_number_total             19018
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9959\% 
 around [-0.00 -0.00 1.00] (reciprocal) or [0.09 0.00 1.00] (direct)
;
_cod_data_source_file            ed5024.cif
_cod_data_source_block           4_x6_cyclohexane
_cod_database_code               1565859
_chemical_oxdiff_formula         'C66 H66 O12 N2'
_chemical_oxdiff_usercomment     'colourless plate, 100 K'
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.919
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6934(10)
 0.3066(10)
2. 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
3. Restrained distances
 C7-C4 = C7-C8 = C7-C9 = C7-C10
 1.54 with sigma of 0.02
 C29-C25 = C29-C30 = C29-C31 = C29-C32
 1.54 with sigma of 0.02
 C51-C47 = C51-C52 = C51-C53 = C51-C54
 1.54 with sigma of 0.02
 C62-C58 = C62-C63 = C62-C64 = C62-C65
 1.54 with sigma of 0.001
 C62-C58 = C62-C63A = C62-C64A = C62-C65A
 1.54 with sigma of 0.001
 C51-C54
 1.54 with sigma of 0.02
 C69-C70
 1.54 with sigma of 0.005
 C70-C71
 1.54 with sigma of 0.005
 C71-C72
 1.54 with sigma of 0.005
 C67-C72
 1.54 with sigma of 0.005
 C67-C68
 1.54 with sigma of 0.005
 C68-C69
 1.54 with sigma of 0.005
 C40-C36 = C40-C42A = C40-C43A = C40-C44A
 1.54 with sigma of 0.001
 C40-C41 = C40-C42 = C40-C43
 1.54 with sigma of 0.001
 C18-C14 = C18-C19 = C18-C20 = C18-C21
 1.54 with sigma of 0.001
 C18-C19A = C18-C20A = C18-C21A
 1.54 with sigma of 0.001
 C63-C64
 2.51 with sigma of 0.04
 C58-C64
 2.51 with sigma of 0.04
 C63-C58
 2.51 with sigma of 0.04
 C63A-C58
 2.51 with sigma of 0.04
 C4-C10
 2.51 with sigma of 0.04
 C4-C9
 2.51 with sigma of 0.04
 C10-C9
 2.51 with sigma of 0.04
 C8-C9
 2.51 with sigma of 0.04
 C8-C10
 2.51 with sigma of 0.04
 C63-C65
 2.51 with sigma of 0.04
 C65-C64
 2.51 with sigma of 0.04
 C65-C58
 2.51 with sigma of 0.04
 C44A-C43A
 2.51 with sigma of 0.04
 C36-C43A
 2.51 with sigma of 0.04
 C36-C44A
 2.51 with sigma of 0.04
 C42A-C44A
 2.51 with sigma of 0.04
 C42A-C36
 2.51 with sigma of 0.04
 C36-C42A
 2.51 with sigma of 0.04
 C21-C19
 2.51 with sigma of 0.04
 C19-C14
 2.51 with sigma of 0.04
 C14-C21
 2.51 with sigma of 0.04
 C19A-C20A
 2.51 with sigma of 0.04
 C21A-C20A
 2.51 with sigma of 0.04
 C21A-C19A
 2.51 with sigma of 0.04
 C14-C19A
 2.51 with sigma of 0.04
 C14-C20A
 2.51 with sigma of 0.04
 C14-C21A
 2.51 with sigma of 0.04
 C20-C19
 2.51 with sigma of 0.04
 C20-C21
 2.51 with sigma of 0.04
 C14-C20
 2.51 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Uanis(C64A) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C63A) = Uanis(C63)
Uanis(C65A) = Uanis(C65)
Uanis(C64) = Uanis(C64A)
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(C42A)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(C43A)=Sof(H43D)=Sof(H43E)=
 Sof(H43F)=Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(H44E)=FVAR(1)
 Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=
 Sof(H20F)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(2)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(2)
 Sof(C63A)=Sof(H63D)=Sof(H63E)=Sof(H63F)=Sof(C64A)=Sof(H64D)=Sof(H64E)=
 Sof(H64F)=Sof(C65A)=Sof(H65D)=Sof(H65E)=Sof(H65F)=1-FVAR(3)
 Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(H63C)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=
 Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=FVAR(3)
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), C67(H67A,H67B), C68(H68A,H68B), C69(H69A,H69B),
 C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5A), C13(H13), C15(H15), C24(H24), C26(H26), C35(H35), C37(H37),
 C46(H46), C48(H48), C57(H57), C59(H59)
6.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), 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),
 C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C19A(H19D,H19E,
 H19F), C20A(H20D,H20E,H20F), C21A(H21D,H21E,H21F), C42A(H42D,H42E,H42F),
 C43A(H43D,H43E,H43F), C44A(H44C,H44D,H44E), C63A(H63D,H63E,H63F), C64A(H64D,
 H64E,H64F), C65A(H65D,H65E,H65F)
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 1.733
_oxdiff_exptl_absorpt_empirical_full_min 0.608
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2