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_1565862
_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, C4 H8 O'
_chemical_formula_sum            'C70 H92 O7'
_chemical_formula_weight         1045.43
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 93.914(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1261(4)
_cell_length_b                   17.8832(4)
_cell_length_c                   19.8489(5)
_cell_measurement_reflns_used    13375
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      76.1640
_cell_measurement_theta_min      3.3130
_cell_volume                     6064.9(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -91.00  42.00   1.00    2.92    --    0.00 -50.00 -99.00  133
  2  \w   -101.00 -35.00   1.00    2.92    --    0.00-178.00-120.00   66
  3  \w      1.00  51.00   1.00    2.92    --    0.00 -99.00  30.00   50
  4  \w      1.00  51.00   1.00    2.92    --    0.00 -99.00-120.00   50
  5  \w   -156.00 -80.00   1.00   11.70    --  -60.50 -94.00  60.00   76
  6  \w    -96.00  -2.00   1.00   11.70    --  -60.50 125.00   0.00   94
  7  \w   -156.00 -80.00   1.00   11.70    --  -60.50 -94.00-180.00   76
  8  \w   -152.00 -19.00   1.00   11.70    --  -60.50 -45.00  90.00  133
  9  \w     94.00 152.00   1.00   11.70    --   60.50 125.00 120.00   58
 10  \w     94.00 152.00   1.00   11.70    --   60.50 125.00  30.00   58
 11  \w     57.00 150.00   1.00   11.70    --  121.00 178.00 -30.00   93
 12  \w    100.00 178.00   1.00   11.70    --  121.00 111.00 -90.00   78
 13  \w     25.00 178.00   1.00   11.70    --  121.00 -12.00   0.00  153
 14  \w     29.00 115.00   1.00   11.70    --  121.00-111.00-150.00   86
 15  \w    100.00 178.00   1.00   11.70    --  121.00 111.00 -30.00   78
 16  \w     30.00 168.00   1.00   11.70    --  121.00 -38.00-120.00  138
 17  \w     57.00 150.00   1.00   11.70    --  121.00 178.00-120.00   93
 18  \w     57.00 150.00   1.00   11.70    --  121.00 178.00 120.00   93
 19  \w     29.00 115.00   1.00   11.70    --  121.00-111.00 120.00   86
 20  \w     28.00 178.00   1.00   11.70    --  121.00 -25.00 150.00  150
 21  \w      1.00  51.00   1.00    2.92    --    0.00 -99.00 120.00   50
 22  \w    -92.00  42.00   1.00    2.92    --    0.00 -57.00-180.00  134
 23  \w     19.00 152.00   1.00   11.70    --   60.50  45.00 -90.00  133
 24  \w   -161.00 -50.00   1.00   11.70    --  -60.50 -77.00   0.00  111
;
_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      -0.0372731000
_diffrn_orient_matrix_UB_12      -0.0478674000
_diffrn_orient_matrix_UB_13      -0.0581759000
_diffrn_orient_matrix_UB_21      -0.0820667000
_diffrn_orient_matrix_UB_22      0.0233497000
_diffrn_orient_matrix_UB_23      0.0194608000
_diffrn_orient_matrix_UB_31      0.0019177000
_diffrn_orient_matrix_UB_32      0.0676961000
_diffrn_orient_matrix_UB_33      -0.0478735000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_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            21493
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.085
_diffrn_reflns_theta_min         3.299
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70543
_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    1.145
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     874
_refine_ls_number_reflns         21493
_refine_ls_number_restraints     169
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0792
_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^)+(0.1618P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2215
_refine_ls_wR_factor_ref         0.2420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14854
_reflns_number_total             21493
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9891\% 
 around [0.00 -0.00 1.00] (reciprocal) or [0.08 -0.00 1.00] (direct)
;
_cod_data_source_file            ed5024.cif
_cod_data_source_block           7_x6_THF
_cod_database_code               1565862
_chemical_oxdiff_formula         'C60 H60 O6 N1'
_chemical_oxdiff_usercomment     '100 K, colourless block'
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.880
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4794(13)
 0.5206(13)
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
 C70A-C67A
 1.54 with sigma of 0.02
 C29-C25 = C29-C30 = C29-C31 = C29-C32 = C29-C30A = C29-C31A = C29-C32A
 1.54 with sigma of 0.001
 C6-C4 = C6-C7A = C6-C8A = C6-C9A = C6-C7 = C6-C8 = C6-C9
 1.54 with sigma of 0.001
 C62-C58 = C62-C63 = C62-C64 = C62-C65 = C62-C63A = C62-C65A = C62-C64A
 1.54 with sigma of 0.001
 C70-C69
 1.54 with sigma of 0.02
 C69A-C70A
 1.54 with sigma of 0.02
 O7-C67 = O7-C70
 1.44 with sigma of 0.02
 C68-C67
 1.54 with sigma of 0.02
 O7A-C68A = O7A-C67A
 1.44 with sigma of 0.02
 C69-C68
 1.54 with sigma of 0.02
 C68A-C69A
 1.54 with sigma of 0.02
 C51A-C47 = C51A-C54A = C51A-C53A = C51A-C52A
 1.54 with sigma of 0.02
 C51-C52 = C51-C53 = C51-C54 = C51-C47
 1.54 with sigma of 0.02
 C67-C69
 2.38 with sigma of 0.04
 C67A-C69A
 2.35 with sigma of 0.04
 C67A-C68A
 2.38 with sigma of 0.04
 O7-C69
 2.38 with sigma of 0.04
 O7-C68
 2.38 with sigma of 0.04
 C4-C7
 2.51 with sigma of 0.04
 C4-C8A
 2.51 with sigma of 0.04
 C9A-C4
 2.51 with sigma of 0.04
 C4-C8
 2.51 with sigma of 0.04
 C9-C4
 2.51 with sigma of 0.04
 C4-C7A
 2.51 with sigma of 0.04
 C65A-C64A
 2.51 with sigma of 0.04
 C65A-C63A
 2.51 with sigma of 0.04
 O7A-C70A
 2.38 with sigma of 0.04
 O7A-C69A
 2.38 with sigma of 0.04
 C64A-C63A
 2.51 with sigma of 0.04
 C9A-C7A
 2.51 with sigma of 0.04
 C9A-C8A
 2.51 with sigma of 0.04
 C63-C64
 2.51 with sigma of 0.04
 C7A-C8A
 2.51 with sigma of 0.04
 C65-C64
 2.51 with sigma of 0.04
 C54A-C53A
 2.51 with sigma of 0.04
 C53A-C47
 2.51 with sigma of 0.04
 C52-C53
 2.51 with sigma of 0.04
 C52A-C47
 2.51 with sigma of 0.04
 C54-C47
 2.51 with sigma of 0.04
 C53-C54
 2.51 with sigma of 0.04
 C52-C47
 2.51 with sigma of 0.04
 C53-C47
 2.51 with sigma of 0.04
 C53A-C52A
 2.51 with sigma of 0.04
 C52-C54
 2.51 with sigma of 0.04
 C52A-C54A
 2.51 with sigma of 0.04
 C54A-C47
 2.51 with sigma of 0.04
4. Rigid bond restraints
 C6, C8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C63, C62
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C68, C67, O7, C70, C69
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C70A, C69A, C68A, O7A, C67A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C68 \\sim C67 \\sim C69 \\sim C70: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
O7A \\sim C68A \\sim H69D \\sim C70A \\sim C67A: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 1.7A
C6 \\sim C8A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C68 \\sim C67 \\sim C69 \\sim O7 \\sim C70: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 1.7A
C70A \\sim C69A \\sim C68A \\sim O7A \\sim C67A: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 1.7A
Uanis(C9A) = Uanis(C9)
Uanis(C65A) = Uanis(C65)
Uanis(C64A) = Uanis(C64)
Uanis(C63A) = Uanis(C63)
6. Rigid body (RIGU) restrains
 C62, C63A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C6, C8A
 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 0.002 and sigma for 1-3 distances of 0.002
7. Others
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=1-FVAR(1)
 Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(C31A)=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=Sof(C32A)=Sof(H32D)=Sof(H32E)=Sof(H32F)=FVAR(1)
 Sof(C70A)=Sof(H70C)=Sof(H70D)=Sof(C69A)=Sof(H69C)=Sof(H69D)=Sof(C68A)=
 Sof(H68C)=Sof(H68D)=Sof(O7A)=Sof(C67A)=Sof(H67C)=Sof(H67D)=1-FVAR(2)
 Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(O7)=Sof(C70)=
 Sof(H70A)=Sof(H70B)=Sof(C69)=Sof(H69A)=Sof(H69B)=FVAR(2)
 Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(H63C)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=
 Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=1-FVAR(3)
 Sof(C63A)=Sof(H63D)=Sof(H63E)=Sof(H63F)=Sof(C65A)=Sof(H65D)=Sof(H65E)=
 Sof(H65F)=Sof(C64A)=Sof(H64D)=Sof(H64E)=Sof(H64F)=FVAR(3)
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=1-FVAR(4)
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=
 Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(4)
 Sof(C54A)=Sof(H54D)=Sof(H54E)=Sof(H54F)=Sof(C53A)=Sof(H53D)=Sof(H53E)=
 Sof(H53F)=Sof(C51A)=Sof(C52A)=Sof(H52D)=Sof(H52E)=Sof(H52F)=1-FVAR(5)
 Sof(C51)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C53)=Sof(H53A)=Sof(H53B)=
 Sof(H53C)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(5)
8.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), C68(H68A,H68B), C67(H67A,H67B), C70(H70A,H70B),
 C69(H69A,H69B), C70A(H70C,H70D), C69A(H69C,H69D), C68A(H68C,H68D), C67A(H67C,
 H67D)
8.b Me refined with riding coordinates:
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C8(H8A,H8B,H8C)
8.c 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), C57(H57), C59(H59)
8.d Idealised Me refined as rotating group:
 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), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C),
 C65(H65A,H65B,H65C), C7A(H7AA,H7AB,H7AC), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C),
 C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F), C32A(H32D,H32E,H32F), C63A(H63D,
 H63E,H63F), C65A(H65D,H65E,H65F), C64A(H64D,H64E,H64F), C52(H52A,H52B,H52C),
 C53(H53A,H53B,H53C), C54(H54A,H54B,H54C), C54A(H54D,H54E,H54F), C53A(H53D,H53E,
 H53F), C52A(H52D,H52E,H52F)
8.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_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.830
_oxdiff_exptl_absorpt_empirical_full_min 0.578
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2