Separation of cyclohexanol from cyclohexanol/cyclohexene mixtures by crystals of pillar[6]arene containing three benzoquinone units.
Liu, Rui; Li, Ming; Liu, Zhongwen; Hua, Bin; Chemical communications (Cambridge, England) 60 (2024) 7626–7629; doi:10.1039/d4cc02407a

data_7133252
_publ_section_title
;
 Separation of cyclohexanol from cyclohexanol/cyclohexene mixtures by
 crystals of pillar[6]arene containing three benzoquinone units.
;
_journal_issue                   59
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7626
_journal_page_last               7629
_journal_paper_doi               10.1039/d4cc02407a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C54 H54 O12, C6 H12 O, C H2 Cl2'
_chemical_formula_sum            'C61 H68 Cl2 O13'
_chemical_formula_weight         1080.05
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-13 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   13.5991(2)
_cell_length_b                   13.5991(2)
_cell_length_c                   52.4778(8)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      4.39
_cell_volume                     8404.8(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      213.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            24838
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.935
_diffrn_reflns_theta_min         4.389
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1324 before and 0.0705 after correction.
The Ratio of minimum to maximum transmission is 0.7701.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             3432
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1358 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.242(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0529
_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^)+(0.1058P)^2^+2.9136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1593
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3060
_reflns_number_total             3530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02407a2.cif
_cod_data_source_block           230505lr
_cod_depositor_comments          'Adding full bibliography for 7133252.cif.'
_cod_original_cell_volume        8404.8(3)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               7133252
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.932
_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
 C19-C20 = C19-C24 = C20-C21 = C21-C22 = C22-C23 = C23-C24
 1.54 with sigma of 0.02
 O5-C19
 1.48 with sigma of 0.01
 Cl2-C25
 1.78 with sigma of 0.02
 Cl3-C25
 1.77 with sigma of 0.02
 Cl2-C25 = Cl3-C25
 1.771 with sigma of 0.01
 Cl2-Cl3
 2.916 with sigma of 0.03
 H5-H20B
 2.1 with sigma of 0.01
 C19-C21 = C19-C23 = C20-C22 = C21-C23 = C22-C24
 2.54 with sigma of 0.04
 Cl2-Cl3
 2.92 with sigma of 0.04
 C20-O5 \\sim O5-C24
 with sigma of 0.02
 C19-C20 \\sim C20-C21 \\sim C21-C22 \\sim C22-C23 \\sim C23-C24 \\sim C24-C19
 with sigma of 0.02
 C19-C23 \\sim C21-C23 \\sim C20-C24 \\sim C20-C22 \\sim C22-C24 \\sim C19-C21
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O5 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Cl2 \\sim Cl3 \\sim C25: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Uanis(C22) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C23) \\sim Ueq, :
with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 C19, C20, C21, C22, C23, C24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2, Cl3, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O5(0.333333) H5(0.333333) C19(0.333333) H19(0.333333)
 C20(0.333333) H20A(0.333333) H20B(0.333333) C21(0.333333) H21A(0.333333)
 H21B(0.333333) C22(0.333333) H22A(0.333333) H22B(0.333333) C23(0.333333)
 H23A(0.333333) H23B(0.333333) C24(0.333333) H24A(0.333333) H24B(0.333333)
 Cl2(0.333333) Cl3(0.333333) C25(0.333333) H25A(0.333333) H25B(0.333333)
6.a Riding coordinates:
 O5(H5)
6.b Ternary CH refined with riding coordinates:
 C19(H19)
6.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B)
6.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C10(H10), C13(H13)
6.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              37643
_olex2_submission_special_instructions 'No special instructions were received'