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_1565854
_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'
_chemical_formula_sum            'C66 H84 O6'
_chemical_formula_weight         973.33
_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
_cell_angle_alpha                114.31(4)
_cell_angle_beta                 91.36(2)
_cell_angle_gamma                91.70(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5900(6)
_cell_length_b                   18.199(7)
_cell_length_c                   18.547(8)
_cell_measurement_reflns_used    799
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      65.9910
_cell_measurement_theta_min      4.5740
_cell_volume                     2946(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.679
_diffrn_measured_fraction_theta_max 0.655
_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    -54.00  42.00   1.00   50.00    --   34.37 -57.00-120.00   96
  2  \w    -32.00  77.00   1.00   50.00    --   34.37 -37.00  90.00  109
  3  \w     23.00  95.00   1.00   50.00    --   34.37-125.00-120.00   72
  4  \w     44.00  74.00   1.00   50.00    --   34.37 -57.00-120.00   30
  5  \w    111.00 146.00   1.00  200.00    --  103.13 -37.00-180.00   35
  6  \w     15.00 121.00   1.00  200.00    --  103.13 -37.00  30.00  106
  7  \w     13.00  72.00   1.00  200.00    --  103.13 -25.00 120.00   59
  8  \w     16.00  49.00   1.00  200.00    --  103.13 -37.00-180.00   33
  9  \w     87.00 164.00   1.00  200.00    --  103.13 -25.00 120.00   77
 10  \w     17.00 145.00   1.00  200.00    --  103.13 -91.00  30.00  128
;
_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      -0.0041506000
_diffrn_orient_matrix_UB_12      0.0887663000
_diffrn_orient_matrix_UB_13      0.0129756000
_diffrn_orient_matrix_UB_21      -0.0242574000
_diffrn_orient_matrix_UB_22      -0.0263926000
_diffrn_orient_matrix_UB_23      -0.0894317000
_diffrn_orient_matrix_UB_31      -0.1589064000
_diffrn_orient_matrix_UB_32      -0.0024107000
_diffrn_orient_matrix_UB_33      0.0096613000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.1499
_diffrn_reflns_Laue_measured_fraction_full 0.679
_diffrn_reflns_Laue_measured_fraction_max 0.655
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8864
_diffrn_reflns_point_group_measured_fraction_full 0.679
_diffrn_reflns_point_group_measured_fraction_max 0.655
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.684
_diffrn_reflns_theta_min         4.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83054
_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    1.097
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.667
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     694
_refine_ls_number_reflns         7289
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.2318
_refine_ls_R_factor_gt           0.1556
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3923
_refine_ls_wR_factor_ref         0.4401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3031
_reflns_number_total             7289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5024.cif
_cod_data_source_block           11_x6_ethyl_acetate
_cod_original_cell_volume        2946.5(19)
_cod_database_code               1565854
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.719
_reflns_odcompleteness_completeness 69.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.70
_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-C9 = C7-C8 = C7-C10 = C7-C4
 1.54 with sigma of 0.005
 C7-C9A = C7-C8A = C7-C10A
 1.54 with sigma of 0.005
 C29-C32
 1.54 with sigma of 0.01
 C40-C41 = C40-C43 = C40-C42 = C40-C36
 1.54 with sigma of 0.01
 C18-C19
 1.54 with sigma of 0.01
 C51-C54 = C51-C47 = C51-C53 = C51-C52
 1.54 with sigma of 0.01
 C18-C20
 1.54 with sigma of 0.01
 C62-C65 = C62-C64 = C62-C63 = C62-C58
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C30 \\sim C32: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C32) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C45)
\\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.02
Uanis(C7) \\sim Ueq, Uanis(C8A) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C50) = Uanis(C49)
Uanis(C8) = Uanis(C8A)
4. Rigid body (RIGU) restrains
 C45, C44
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C57, C56
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C18, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C25, C26
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C44, C45
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C51, C53
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C59, C60
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C29, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C29, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C10A)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B), C33(H33A,H33B), C44(H44A,H44B), C22(H22A,H22B), C66(H66A,
 H66B), C11(H11A,H11B)
6.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C48(H48), C35(H35), C24(H24), C37(H37), C46(H46), C59(H59),
 C57(H57), C5(H5A), C13(H13), C3(H3A), C15(H15)
6.c Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C53(H53A,H53B,H53C), C30(H30A,H30B,H30C), C63(H63A,H63B,
 H63C), C52(H52A,H52B,H52C), C21(H21A,H21B,H21C), C41(H41A,H41B,H41C), C65(H65A,
 H65B,H65C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C64(H64A,H64B,H64C),
 C43(H43A,H43B,H43C), C42(H42A,H42B,H42C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C9A(H9AA,H9AB,
 H9AC), C10A(H10D,H10E,H10F), C8A(H8AA,H8AB,H8AC)
6.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O4(H4), O1(H1), O2(H2), O6(H6)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.614
_oxdiff_exptl_absorpt_empirical_full_min 0.532