Adsorptive Separation of Cyclohexanol and Cyclohexanone by Nonporous Adaptive Crystals of RhombicArene
Zhao, Yong-Ye; xiao, hongyan; Tung, Chen-Ho; Wu, Li-Zhu; Cong, Huan; Chemical Science  (2021) –; doi:10.1039/D1SC04728K

data_1565345
_publ_section_title
;
 Adsorptive Separation of Cyclohexanol and Cyclohexanone by Nonporous
 Adaptive Crystals of RhombicArene
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04728K
_journal_year                    2021
_chemical_formula_moiety         'C74 H76 O12, C6 H10 O, C4 H10 O'
_chemical_formula_sum            'C84 H96 O14'
_chemical_formula_weight         1329.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-03-02 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.7110(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.71520(10)
_cell_length_b                   15.94590(10)
_cell_length_c                   18.62990(10)
_cell_measurement_reflns_used    42503
_cell_measurement_temperature    170.00(12)
_cell_measurement_theta_max      74.9940
_cell_measurement_theta_min      2.4160
_cell_volume                     3958.28(5)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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    -82.00  -5.00   0.50    0.20    --  -47.20 103.00  92.00  154
  2  \w      5.00  70.00   0.50    0.20    --   47.20-103.00  -9.00  130
  3  \w   -153.00-126.00   0.50    0.80    --  -99.00-103.00  -9.00   54
  4  \w    -90.00 -65.00   0.50    0.80    --  -99.00 103.00  92.00   50
  5  \w    105.00 132.00   0.50    0.80    --  103.25 103.00  92.00   54
  6  \w     67.00 102.00   0.50    0.80    --  103.25-103.00  -9.00   70
  7  \w   -103.00 -72.00   0.50    0.20    --  -47.20 -77.00 -60.00   62
  8  \w    -40.00  26.00   0.50    0.20    --  -47.20  38.00 -30.00  132
  9  \w   -120.00 -82.00   0.50    0.20    --  -47.20-125.00 120.00   76
 10  \w   -107.00 -74.00   0.50    0.20    --  -47.20-125.00 150.00   66
 11  \w     13.00  46.00   0.50    0.20    --   47.20 -38.00 -30.00   66
 12  \w    -19.00  29.00   0.50    0.20    --   47.20 -19.00  60.00   96
 13  \w    -24.00  47.00   0.50    0.20    --   47.20 -38.00  30.00  142
 14  \w    -51.00 -26.00   0.50    0.80    --  -99.00 125.00-120.00   50
 15  \w   -118.00 -89.00   0.50    0.80    --  -99.00 -49.00 -97.80   58
 16  \w   -108.00 -68.00   0.50    0.80    --  -99.00 112.00 -47.28   80
 17  \w   -112.00 -74.00   0.50    0.80    --  -99.00 125.00-120.00   76
 18  \w    -65.00 -39.00   0.50    0.80    --  -99.00  61.00-120.00   52
 19  \w   -167.00-122.00   0.50    0.80    --  -99.00 -49.00 -97.80   90
 20  \w   -112.00 -42.00   0.50    0.80    --  -99.00 125.00  60.00  140
 21  \w   -167.00 -86.00   0.50    0.80    --  -99.00 -54.00-108.91  162
 22  \w   -111.00 -58.00   0.50    0.80    --  -99.00 125.00  90.00  106
 23  \w   -167.00 -91.00   0.50    0.80    --  -99.00 -94.00 -30.00  152
 24  \w   -126.00 -76.00   0.50    0.80    --  -99.00 144.00  -1.02  100
 25  \w   -112.00 -80.00   0.50    0.80    --  -99.00 -77.00  60.00   64
 26  \w    -59.00 -32.00   0.50    0.80    --  -99.00 112.00 -47.28   54
 27  \w   -104.00 -38.00   0.50    0.80    --  -99.00 125.00 120.00  132
 28  \w    -58.00 -26.00   0.50    0.80    --  -99.00  61.00  90.00   64
 29  \w   -156.00 -80.00   0.50    0.80    --  -99.00 -67.00  31.14  152
 30  \w    -68.00 -27.00   0.50    0.80    --  -99.00  61.00 -90.00   82
 31  \w     37.00  85.00   0.50    0.80    --  103.25-125.00  60.00   96
 32  \w     98.00 165.00   0.50    0.80    --  103.25  15.00 150.00  134
 33  \w     31.00 102.00   0.50    0.80    --  103.25-125.00-180.00  142
 34  \w     55.00 111.00   0.50    0.80    --  103.25-125.00   0.00  112
 35  \w    127.00 168.00   0.50    0.80    --  103.25  45.00  30.00   82
 36  \w    143.00 169.00   0.50    0.80    --  103.25  45.00-180.00   52
 37  \w     47.00  74.00   0.50    0.80    --  103.25 -61.00  30.00   54
 38  \w     57.00  83.00   0.50    0.80    --  103.25 -94.00 -90.00   52
 39  \w     31.00  70.00   0.50    0.80    --  103.25 -61.00 -30.00   78
 40  \w     90.00 164.00   0.50    0.80    --  103.25  15.00   0.00  148
 41  \w    132.00 157.00   0.50    0.80    --  103.25  45.00-150.00   50
 42  \w     31.00  74.00   0.50    0.80    --  103.25 -61.00 -90.00   86
 43  \w     41.00  75.00   0.50    0.80    --  103.25 -61.00   0.00   68
 44  \w     92.00 169.00   0.50    0.80    --  103.25  45.00  60.00  154
 45  \w     92.00 124.00   0.50    0.80    --  103.25  45.00-180.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0630981000
_diffrn_orient_matrix_UB_12      0.0696083000
_diffrn_orient_matrix_UB_13      -0.0464203000
_diffrn_orient_matrix_UB_21      0.0890205000
_diffrn_orient_matrix_UB_22      0.0611108000
_diffrn_orient_matrix_UB_23      0.0223663000
_diffrn_orient_matrix_UB_31      0.0381004000
_diffrn_orient_matrix_UB_32      -0.0274616000
_diffrn_orient_matrix_UB_33      -0.0678017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            57056
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.374
_diffrn_reflns_theta_min         2.441
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84128
_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    1.116
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 6737 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     916
_refine_ls_number_reflns         15673
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.5225P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                15007
_reflns_number_total             15673
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04728k2.cif
_cod_data_source_block           tx5125_sq
_cod_database_code               1565345
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 100.00
_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. Restrained distances
 C51A-C50A = C51-C50 = C52-C51 = C52-C51A
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C50 \\sim C51 \\sim C51A \\sim C50A: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 1.7A
Uanis(C51) \\sim Ueq, Uanis(C51A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(H49C)=Sof(H49D)=Sof(H52C)=Sof(H52D)=Sof(C51A)=Sof(H51C)=Sof(H51D)=
 Sof(C50A)=Sof(H50C)=Sof(H50D)=1-FVAR(1)
 Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C51)=Sof(H51A)=Sof(H51B)=
 Sof(H52A)=Sof(H52B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B), C16(H16A,H16B), C28(H28A,H28B), C40(H40A,H40B),
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C49(H49A,H49B), C49(H49C,H49D),
  C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C52(H52C,H52D), C65(H65A,
 H65B), C75(H75A,H75B), C76(H76A,H76B), C77(H77A,H77B), C78(H78A,H78B),
 C79(H79A,H79B), C81(H81A,H81B), C82(H82A,H82B), C51A(H51C,H51D), C50A(H50C,
 H50D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C22(H22), C25(H25), C31(H31), C34(H34), C38(H38), C54(H54),
 C58(H58), C61(H61), C67(H67), C70(H70)
5.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C72(H72A,H72B,H72C), C73(H73A,
 H73B,H73C), C80(H80A,H80B,H80C), C83(H83A,H83B,H83C)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O7(H7), O8(H8)
;
_shelx_res_checksum              21794
_shelx_hkl_checksum              41872
_shelx_fab_checksum              79036
_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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.535