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_1565857
_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, 3(C6 H6)'
_chemical_formula_sum            'C84 H102 O6'
_chemical_formula_weight         1207.65
_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
_atom_sites_solution_primary     dual
_cell_angle_alpha                80.680(4)
_cell_angle_beta                 72.393(5)
_cell_angle_gamma                78.191(4)
_cell_formula_units_Z            2
_cell_length_a                   13.5391(8)
_cell_length_b                   14.7702(6)
_cell_length_c                   19.0450(10)
_cell_measurement_reflns_used    11593
_cell_measurement_temperature    100.00(12)
_cell_measurement_theta_max      76.9370
_cell_measurement_theta_min      3.0640
_cell_volume                     3532.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      0.0018976000
_diffrn_orient_matrix_UB_12      0.0027633000
_diffrn_orient_matrix_UB_13      0.0800920000
_diffrn_orient_matrix_UB_21      0.1194270000
_diffrn_orient_matrix_UB_22      -0.0347009000
_diffrn_orient_matrix_UB_23      -0.0221961000
_diffrn_orient_matrix_UB_31      0.0196510000
_diffrn_orient_matrix_UB_32      0.1013644000
_diffrn_orient_matrix_UB_33      -0.0194600000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23648
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.076
_diffrn_reflns_theta_min         2.448
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_description       plate
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     919
_refine_ls_number_reflns         23648
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0887P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17758
_reflns_number_total             23648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5024.cif
_cod_data_source_block           1_x6_benzene
_cod_database_code               1565857
_chemical_oxdiff_formula         'c84 h102 o6'
_chemical_oxdiff_usercomment     '100 K'
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5005(6)
 0.4995(6)
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
 C18-C19 = C18-C20 = C18-C14
 1.53 with sigma of 0.005
 C19-C21
 2.51 with sigma of 0.04
 C20-C19
 2.51 with sigma of 0.04
 C19-C14
 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
 C14-C21
 2.51 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
C18 \\sim C21: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C18 \\sim C19: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C18 \\sim C20: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C21) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02
Uanis(C18) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C20, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C83A)=Sof(H83A)=Sof(C79A)=Sof(H79A)=Sof(C80A)=Sof(H80A)=Sof(C81A)=
 Sof(H81A)=Sof(C82A)=Sof(H82A)=Sof(C84A)=Sof(H84A)=1-FVAR(1)
 Sof(C81)=Sof(H81)=Sof(C82)=Sof(H82)=Sof(C83)=Sof(H83)=Sof(C84)=Sof(H84)=
 Sof(C79)=Sof(H79)=Sof(C80)=Sof(H80)=FVAR(1)
 Sof(C18A)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C21A)=Sof(H21D)=
 Sof(H21E)=Sof(H21F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(2)
 Sof(C18)=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)
7.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)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5A), C13(H13), C15(H15), C24(H24), C26(H26), C35(H35), C37(H37),
 C47(H47), C49(H49), C59(H59), C61(H61), C67(H67), C68(H68), C69(H69), C70(H70),
  C71(H71), C72(H72), C73(H73), C74(H74), C75(H75), C76(H76), C77(H77),
 C78(H78), C83A(H83A), C79A(H79A), C80A(H80A), C81A(H81A), C82A(H82A),
 C84A(H84A), C81(H81), C82(H82), C83(H83), C84(H84), C79(H79), C80(H80)
7.c Fitted hexagon refined as free rotating group:
 C81(C82,C83,C84,C79,C80)
7.d 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), C21A(H21D,H21E,H21F), C20A(H20D,H20E,H20F)
7.e 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_full_max 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.676
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2