Facile separation of cyclic aliphatic and aromatic vapors using crystalline thiacalixarene assemblies with preorganized channels.
Yamada, Manabu; Yoshizaki, Ruka; Uemura, Fumiya; Katagiri, Hiroshi; Kato, Sumio; Akimoto, Kazuhiko; Hamada, Fumio; Chemical communications (Cambridge, England) 59 (2023) 2604–2607; doi:10.1039/d2cc05647j

data_7131342
_publ_section_title
;
 Facile separation of cyclic aliphatic and aromatic vapors using
 crystalline thiacalixarene assemblies with preorganized channels.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2604
_journal_page_last               2607
_journal_paper_doi               10.1039/d2cc05647j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C36 H36 Br4 O4 S4, C6 H6'
_chemical_formula_sum            'C42 H42 Br4 O4 S4'
_chemical_formula_weight         1058.63
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-10-11 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   31.1234(3)
_cell_length_b                   31.1234(3)
_cell_length_c                   24.1605(2)
_cell_measurement_reflns_used    11899
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      76.7030
_cell_measurement_theta_min      2.4640
_cell_volume                     20268.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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      223.00(10)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_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    -55.00  15.00   0.50    0.47    --  -42.80  79.00 145.00  140
  2  \w     -4.00  36.00   0.50    0.47    --  -42.80  19.00  30.00   80
  3  \w    -37.00   0.00   0.50    0.47    --   42.80 -19.00  30.00   74
  4  \w     46.00  72.00   0.50    1.88    --  111.75 -61.00 150.00   52
  5  \w     41.00 103.00   0.50    1.88    --  111.75-125.00 150.00  124
  6  \w     45.00  72.00   0.50    1.88    --  111.75 -61.00  30.00   54
  7  \w     38.00  63.00   0.50    1.88    --  111.75 -61.00 -30.00   50
  8  \w     44.00  70.00   0.50    1.88    --  111.75 -61.00 -60.00   52
  9  \w     49.00  75.00   0.50    1.88    --  111.75 -61.00 -90.00   52
 10  \w     48.00 107.00   0.50    1.88    --  111.75-131.00 -78.00  118
 11  \w    118.00 169.00   0.50    1.88    --  111.75  77.00  60.00  102
 12  \w    140.00 172.00   0.50    1.88    --  111.75  93.00 159.00   64
 13  \w    108.00 137.00   0.50    1.88    --  111.75  93.00 159.00   58
 14  \w    -60.00 -35.00   0.50    1.88    --  -90.25  93.00 159.00   50
 15  \w    -49.00 -15.00   0.50    1.88    --  -90.25  45.00-120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-DW'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0469138000
_diffrn_orient_matrix_UB_12      -0.0417585000
_diffrn_orient_matrix_UB_13      -0.0277780000
_diffrn_orient_matrix_UB_21      -0.0095129000
_diffrn_orient_matrix_UB_22      0.0389909000
_diffrn_orient_matrix_UB_23      -0.0278127000
_diffrn_orient_matrix_UB_31      0.0312514000
_diffrn_orient_matrix_UB_32      0.0014855000
_diffrn_orient_matrix_UB_33      -0.0502131000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22078
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.258
_diffrn_reflns_theta_min         2.840
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    6.403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.561
_exptl_crystal_description       block
_exptl_crystal_F_000             9540
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: benzene'
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.389
_exptl_crystal_size_min          0.356
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     245
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0817P)^2^+77.7230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4158
_reflns_number_total             4687
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05647j2.cif
_cod_data_source_block           sx19083
_cod_original_cell_volume        20268.0(4)
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               7131342
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O Br S'
_shelx_estimated_absorpt_t_max   0.209
_shelx_estimated_absorpt_t_min   0.190
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 C(H,H,H,H,H,H) groups
2. Restrained distances
 C16-C17 \\sim C16-C7A
 with sigma of 0.02
 C18-C17 \\sim C18-C7A
 with sigma of 0.02
 C30-C25 \\sim C25-C26 \\sim C27-C26 \\sim C27-C28 \\sim C28-C29 \\sim C29-C30
 with sigma of 0.02
 C28-C30 \\sim C29-C25 \\sim C30-C26 \\sim C25-C27 \\sim C29-C27
 with sigma of 0.02
 C19-C20 \\sim C20-C21 \\sim C21-C22 \\sim C23-C22 \\sim C23-C24 \\sim C24-C19
 with sigma of 0.02
 C19-C21 \\sim C20-C22 \\sim C21-C23 \\sim C22-C24 \\sim C24-C20 \\sim C19-C21
 with sigma of 0.02
3. Restrained planarity
 C26, C30, C28, C25, C27, C29
 with sigma of 0.1
 C22, C24, C20, C23
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C25 \\sim C26 \\sim C27 \\sim C30 \\sim C28 \\sim C29: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C21 \\sim C20 \\sim C19 \\sim C24 \\sim C23 \\sim C22: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C16 \\sim C17 \\sim C7A \\sim C18: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C30, C26, C25, C27, C28, C29
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C23, C24, C19, C20, C21, C22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C17, C7A, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H16C)=Sof(H16D)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C7A)=Sof(H7AA)=
 Sof(H7AB)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C17)=Sof(H17A)=
 Sof(H17B)=FVAR(1)
 Fixed Sof: C26(0.16667) H26(0.16667) C25(0.16667) H25(0.16667) C30(0.16667)
 H30(0.16667) C29(0.16667) H29(0.16667) C28(0.16667) H28(0.16667) C27(0.16667)
 H27(0.16667) C22(0.33333) H22(0.33333) C21(0.33333) H21(0.33333) C20(0.33333)
 H20(0.33333) C19(0.33333) H19(0.33333) C24(0.33333) H24(0.33333) C23(0.33333)
 H23(0.33333)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B), C16(H16C,H16D), C8(H8A,H8B), C17(H17A,H17B),
 C7A(H7AA,H7AB)
7.b Me refined with riding coordinates:
 C18(H18A,H18B,H18C), C18(H18D,H18E,H18F)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C6(H6), C15(H15), C26(H26), C25(H25), C30(H30), C29(H29),
 C28(H28), C27(H27), C22(H22), C21(H21), C20(H20), C19(H19), C24(H24), C23(H23)
7.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              60884
_shelx_hkl_checksum              58025
_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 1.703
_oxdiff_exptl_absorpt_empirical_full_min 0.565