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_1565855
_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         '4(C H2 Cl2), C66 H84 O6'
_chemical_formula_sum            'C70 H92 Cl8 O6'
_chemical_formula_weight         1313.03
_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     direct
_cell_angle_alpha                77.127(3)
_cell_angle_beta                 66.915(4)
_cell_angle_gamma                76.404(3)
_cell_formula_units_Z            2
_cell_length_a                   13.8727(6)
_cell_length_b                   16.0717(6)
_cell_length_c                   17.6177(6)
_cell_measurement_reflns_used    15478
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      71.4740
_cell_measurement_theta_min      2.7740
_cell_volume                     3474.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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    'ShelXS (Sheldrick, 2008)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.979
_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    -42.00  92.00   1.00    1.00    --    0.00  57.00-120.00  134
  2  \w    -99.00 -34.00   1.00    1.00    --    0.00 178.00 -30.00   65
  3  \w      1.00  51.00   1.00    1.00    --    0.00 -99.00 -90.00   50
  4  \w   -151.00 -80.00   1.00    1.00    --  -55.02 -94.00-150.00   71
  5  \w   -146.00 -13.00   1.00    1.00    --  -55.02 -45.00-150.00  133
  6  \w   -101.00  -8.00   1.00    1.00    --  -55.02 135.00 140.00   93
  7  \w     -2.00 147.00   1.00    1.00    --   55.02  30.00 120.00  149
  8  \w     94.00 146.00   1.00    1.00    --   55.02 125.00  90.00   52
  9  \w     94.00 146.00   1.00    1.00    --   55.02 125.00 120.00   52
 10  \w     94.00 146.00   1.00    1.00    --   55.02 125.00-120.00   52
 11  \w     23.00 121.00   1.00    1.00    --   55.02-125.00 -90.00   98
 12  \w     94.00 146.00   1.00    1.00    --   55.02 125.00 -90.00   52
 13  \w     94.00 146.00   1.00    1.00    --   55.02 125.00-180.00   52
 14  \w     18.00 115.00   1.00   10.00    --  110.04-111.00-150.00   97
 15  \w     57.00 150.00   1.00   10.00    --  110.04 178.00  90.00   93
 16  \w    100.00 178.00   1.00   10.00    --  110.04 111.00 -30.00   78
 17  \w     18.00 115.00   1.00   10.00    --  110.04-111.00 150.00   97
 18  \w    100.00 178.00   1.00   10.00    --  110.04 111.00-180.00   78
 19  \w     13.00 158.00   1.00   10.00    --  110.04 -91.00-120.00  145
 20  \w    100.00 178.00   1.00   10.00    --  110.04 111.00 -90.00   78
 21  \w     18.00 115.00   1.00   10.00    --  110.04-111.00  60.00   97
 22  \w    100.00 178.00   1.00   10.00    --  110.04 111.00-150.00   78
 23  \w     19.00 157.00   1.00   10.00    --  110.04 -38.00-150.00  138
 24  \w     10.00 178.00   1.00   10.00    --  110.04   0.00 -30.00  168
 25  \w     19.00 152.00   1.00   10.00    --  110.04 -50.00-120.00  133
 26  \w      1.00  51.00   1.00    1.00    --    0.00 -99.00 -60.00   50
 27  \w    -44.00 100.00   1.00    1.00    --    0.00  77.00   0.00  144
 28  \w   -148.00 -12.00   1.00    1.00    --  -55.02 -61.00 -30.00  136
 29  \w   -155.00 -11.00   1.00    1.00    --  -55.02 -77.00  60.00  144
 30  \w   -155.00 -11.00   1.00    1.00    --  -55.02 -77.00 -90.00  144
 31  \w   -155.00 -11.00   1.00    1.00    --  -55.02 -77.00-150.00  144
;
_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      0.1057383000
_diffrn_orient_matrix_UB_12      0.0340527000
_diffrn_orient_matrix_UB_13      -0.0296414000
_diffrn_orient_matrix_UB_21      -0.0123069000
_diffrn_orient_matrix_UB_22      -0.0035415000
_diffrn_orient_matrix_UB_23      0.0913978000
_diffrn_orient_matrix_UB_31      0.0603891000
_diffrn_orient_matrix_UB_32      -0.0936251000
_diffrn_orient_matrix_UB_33      0.0007067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40412
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.736
_diffrn_reflns_theta_min         2.756
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.937
_refine_diff_density_min         -1.196
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     808
_refine_ls_number_reflns         13310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0724
_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^)+(0.1384P)^2^+4.0386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10893
_reflns_number_total             13310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ed5024.cif
_cod_data_source_block           12_x6_DCM_1_4
_cod_database_code               1565855
_chemical_oxdiff_formula         'C48 H60 O6 N1'
_shelx_estimated_absorpt_t_max   0.731
_shelx_estimated_absorpt_t_min   0.634
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl2) = Uanis(Cl2A)
Uanis(C54A) = Uanis(C54)
Uanis(C53) = Uanis(C53A)
Uanis(C52) = Uanis(C52A)
3. Others
 Sof(Cl2)=Sof(H67C)=Sof(H67D)=1-FVAR(1)
 Sof(Cl2A)=Sof(H67A)=Sof(H67B)=FVAR(1)
 Sof(Cl4)=Sof(H68C)=Sof(H68D)=1-FVAR(2)
 Sof(Cl4A)=Sof(H68A)=Sof(H68B)=FVAR(2)
 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(3)
 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(3)
4.a Secondary CH2 refined with riding coordinates:
 C67(H67A,H67B), C67(H67C,H67D), C68(H68A,H68B), C68(H68C,H68D), C69(H69A,
 H69B), C70(H70A,H70B), C11(H11A,H11B), C22(H22A,H22B), C33(H33A,H33B),
 C44(H44A,H44B), C55(H55A,H55B), C66(H66A,H66B)
4.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)
4.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), C52A(H52D,H52E,H52F), C53(H53A,H53B,H53C),
 C53A(H53D,H53E,H53F), C54(H54A,H54B,H54C), C54A(H54D,H54E,H54F), C63(H63A,H63B,
 H63C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6)
;
_olex2_date_sample_data_collection 2017-11-04
_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 2.380
_oxdiff_exptl_absorpt_empirical_full_min 0.567