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_1565860
_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'
_chemical_formula_sum            'C73 H92 O6'
_chemical_formula_weight         1065.46
_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
_cell_angle_alpha                90
_cell_angle_beta                 95.843(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1817(6)
_cell_length_b                   18.7393(6)
_cell_length_c                   19.4157(6)
_cell_measurement_reflns_used    3809
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      46.9300
_cell_measurement_theta_min      4.0120
_cell_volume                     6218.9(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 (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      100.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_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      1.00  50.00   1.00   17.63    --    0.00 -99.00-180.00   49
  2  \w    -40.00  90.00   1.00   17.63    --    0.00  57.00-120.00  130
  3  \w    -96.00  -2.00   1.00   70.49    --  -59.50 125.00 -30.00   94
  4  \w     94.00 148.00   1.00   70.49    --   59.50 125.00 120.00   54
  5  \w     94.00 148.00   1.00   70.49    --   59.50 125.00-180.00   54
  6  \w     94.00 148.00   1.00   70.49    --   59.50 125.00  60.00   54
  7  \w    -34.00  66.00   1.00   70.49    --   59.50 -15.00 -90.00  100
;
_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      -0.0024636000
_diffrn_orient_matrix_UB_12      0.0803965000
_diffrn_orient_matrix_UB_13      -0.0165914000
_diffrn_orient_matrix_UB_21      0.0830197000
_diffrn_orient_matrix_UB_22      -0.0045166000
_diffrn_orient_matrix_UB_23      -0.0230144000
_diffrn_orient_matrix_UB_31      -0.0349204000
_diffrn_orient_matrix_UB_32      -0.0165637000
_diffrn_orient_matrix_UB_33      -0.0745790000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11419
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        46.850
_diffrn_reflns_theta_max         46.850
_diffrn_reflns_theta_min         3.274
_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  0.89613
_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    1.138
_exptl_crystal_description       block
_exptl_crystal_F_000             2312
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     799
_refine_ls_number_reflns         5095
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.225
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0651
_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^)+(0.0466P)^2^+17.3694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1671
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4242
_reflns_number_total             5095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5024.cif
_cod_data_source_block           5_x6_toluene
_cod_original_cell_volume        6218.9(3)
_cod_database_code               1565860
_chemical_oxdiff_formula         'C50 H30 O6 '
_chemical_oxdiff_usercomment     'colourless needle, 100 K'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.948
_reflns_odcompleteness_completeness 89.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     47.25
_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
 1.54 with sigma of 0.02
 C62-C58 = C62-C63 = C62-C64 = C62-C65
 1.54 with sigma of 0.02
 C40-C36 = C40-C41 = C40-C42 = C40-C43
 1.54 with sigma of 0.02
 C18-C14 = C18-C19 = C18-C20 = C18-C21
 1.54 with sigma of 0.02
 C51-C47 = C51-C52 = C51-C53 = C51-C54 = C51-C52A = C51-C53A = C51-C54A
 1.54 with sigma of 0.005
 C29-C25 = C29-C30 = C29-C31 = C29-C32
 1.54 with sigma of 0.005
 C7-C8A
 1.54 with sigma of 0.02
 C7-C4 = C7-C8 = C7-C9 = C7-C10 = C7-C8A = C7-C9A = C7-C10A
 1.54 with sigma of 0.01
 C54A-C52A
 2.51 with sigma of 0.04
 C8-C4
 2.51 with sigma of 0.04
 C47-C52A
 2.51 with sigma of 0.04
 C47-C54
 2.51 with sigma of 0.04
 C47-C52
 2.51 with sigma of 0.04
 C9-C10
 2.51 with sigma of 0.04
 C9-C4
 2.51 with sigma of 0.04
 C53A-C54A
 2.51 with sigma of 0.04
 C8-C10
 2.51 with sigma of 0.04
 C53A-C52A
 2.51 with sigma of 0.04
 C53-C52
 2.51 with sigma of 0.04
 C54-C53
 2.51 with sigma of 0.04
 C8-C9
 2.51 with sigma of 0.04
 C47-C54A
 2.51 with sigma of 0.04
 C52-C54
 2.51 with sigma of 0.04
 C47-C53
 2.51 with sigma of 0.04
 C4-C10
 2.51 with sigma of 0.04
 C47-C53A
 2.51 with sigma of 0.04
 C4-C10A
 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
 C9A-C10A
 2.51 with sigma of 0.04
 C4-C9A
 2.51 with sigma of 0.04
 C8A-C9A
 2.51 with sigma of 0.04
3. Rigid bond restraints
 C7, C8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C51 \\sim C52: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
C7 \\sim C8A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(O2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.1
Uanis(C58) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C8A) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=1-FVAR(1)
 Sof(C52A)=Sof(H52D)=Sof(H52E)=Sof(H52F)=Sof(C53A)=Sof(H53D)=Sof(H53E)=
 Sof(H53F)=Sof(C54A)=Sof(H54D)=Sof(H54E)=Sof(H54F)=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(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(2)
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), C24(H24), C26(H26), C35(H35), C37(H37),
 C46(H46), C48(H48), C57(H57), C59(H59), C68(H68), C69(H69), C70(H70), C71(H71),
  C72(H72)
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), C8A(H8AA,H8AB,
 H8AC), C9A(H9AA,H9AB,H9AC), C10A(H10D,H10E,H10F), C52A(H52D,H52E,H52F),
 C53A(H53D,H53E,H53F), C54A(H54D,H54E,H54F), C73(H73A,H73B,H73C)
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 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.695