Adsorptive separation of picoline isomers by adaptive calix[3]acridan crystals
Zhou, He-Ye; Chen, Chuan-Feng; Chemical Communications  (2022) –; doi:10.1039/D2CC00943A

data_7129784
_publ_section_title
;
 Adsorptive separation of picoline isomers by adaptive calix[3]acridan
 crystals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00943A
_journal_year                    2022
_chemical_formula_moiety         'C51 H51 N3, 2(C6 H7 N)'
_chemical_formula_sum            'C63 H65 N5'
_chemical_formula_weight         892.20
_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
_audit_creation_date             2021-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-04 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                73.661(2)
_cell_angle_beta                 82.2150(10)
_cell_angle_gamma                84.642(2)
_cell_formula_units_Z            2
_cell_length_a                   9.27290(10)
_cell_length_b                   13.6876(3)
_cell_length_c                   20.4931(4)
_cell_measurement_reflns_used    26680
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      75.0750
_cell_measurement_theta_min      3.3480
_cell_volume                     2468.83(8)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.952
_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    -63.00  23.00   0.50    0.05    --  -47.57  84.00 164.00  172
  2  \w    -23.00  11.00   0.50    0.05    --   47.57 -84.00  44.00   68
  3  \w     14.00  51.00   0.50    0.05    --   47.57 -84.00  44.00   74
  4  \w    -76.00 -50.00   0.50    0.05    --  -99.00  84.00 164.00   52
  5  \w   -168.00 -91.00   0.50    0.05    --  -99.00 -84.00  44.00  154
  6  \w     86.00 163.00   0.50    0.05    --  103.25  84.00 164.00  154
  7  \w   -117.00 -86.00   0.50    0.05    --  -47.57-125.00 -60.00   62
  8  \w    -39.00  20.00   0.50    0.05    --  -47.57  38.00 -30.00  118
  9  \w    -22.00  11.00   0.50    0.05    --  -47.57  19.00 120.00   66
 10  \w    -19.00   6.00   0.50    0.05    --  -47.57  19.00-120.00   50
 11  \w   -115.00 -79.00   0.50    0.05    --  -47.57-125.00 120.00   72
 12  \w   -104.00 -77.00   0.50    0.05    --  -47.57-125.00 150.00   54
 13  \w    -22.00  10.00   0.50    0.05    --  -47.57  19.00  90.00   64
 14  \w    -26.00  16.00   0.50    0.05    --   47.57 -19.00 120.00   84
 15  \w    -68.00 -43.00   0.50    0.05    --  -99.00  61.00   0.00   50
 16  \w    -66.00 -40.00   0.50    0.05    --  -99.00  61.00-180.00   52
 17  \w    -68.00 -30.00   0.50    0.05    --  -99.00  61.00 -90.00   76
 18  \w   -109.00 -26.00   0.50    0.05    --  -99.00 118.00 -44.74  166
 19  \w   -159.00 -82.00   0.50    0.05    --  -99.00 -62.00 -98.93  154
 20  \w   -112.00 -60.00   0.50    0.05    --  -99.00 125.00 120.00  104
 21  \w    -78.00 -43.00   0.50    0.05    --  -99.00  77.00  90.00   70
 22  \w   -167.00 -86.00   0.50    0.05    --  -99.00 -45.00 -90.00  162
 23  \w   -102.00 -28.00   0.50    0.05    --  -99.00 125.00 -90.00  148
 24  \w    -62.00 -27.00   0.50    0.05    --  -99.00 125.00-180.00   70
 25  \w   -142.00 -90.00   0.50    0.05    --  -99.00 -94.00 150.00  104
 26  \w   -112.00 -67.00   0.50    0.05    --  -99.00 125.00-180.00   90
 27  \w   -112.00 -86.00   0.50    0.05    --  -99.00 125.00-150.00   52
 28  \w    -95.00 -27.00   0.50    0.05    --  -99.00 125.00  90.00  136
 29  \w   -122.00 -32.00   0.50    0.05    --  -99.00 140.00  45.09  180
 30  \w     32.00 106.00   0.50    0.05    --  103.25 -94.00-150.00  148
 31  \w     64.00  90.00   0.50    0.05    --  103.25 -94.00   0.00   52
 32  \w     32.00 104.00   0.50    0.05    --  103.25-125.00  60.00  144
 33  \w    138.00 164.00   0.50    0.05    --  103.25  15.00 120.00   52
 34  \w     90.00 135.00   0.50    0.05    --  103.25  15.00 120.00   90
 35  \w     88.00 168.00   0.50    0.05    --  103.25  61.00 -60.00  160
 36  \w     37.00  76.00   0.50    0.05    --  103.25 -94.00-180.00   78
 37  \w     47.00 106.00   0.50    0.05    --  103.25 -94.00 -90.00  118
 38  \w     94.00 120.00   0.50    0.05    --  103.25  15.00  90.00   52
 39  \w     41.00  81.00   0.50    0.05    --  103.25 -84.00  44.00   80
;
_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      -0.1585621000
_diffrn_orient_matrix_UB_12      0.0171118000
_diffrn_orient_matrix_UB_13      -0.0173355000
_diffrn_orient_matrix_UB_21      -0.0484672000
_diffrn_orient_matrix_UB_22      0.0299286000
_diffrn_orient_matrix_UB_23      0.0670581000
_diffrn_orient_matrix_UB_31      0.0268581000
_diffrn_orient_matrix_UB_32      0.1123144000
_diffrn_orient_matrix_UB_33      -0.0376930000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32982
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.299
_diffrn_reflns_theta_min         2.261
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92583
_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            'translucent light colourless'
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       cube
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         9747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0678P)^2^+1.1012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9300
_reflns_number_total             9747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00943a2.cif
_cod_data_source_block           tx6081a
_cod_database_code               7129784
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHN
_reflns_odcompleteness_completeness 99.49
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C23(H23A,H23B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C37(H37), C38(H38), C21(H21), C7(H7), C2(H2), C42(H42),
 C25(H25), C47(H47), C41(H41), C46(H46), C39(H39), C33(H33), C30(H30), C3(H3),
 C29(H29), C40(H40), C57(H57), C60(H60), C64(H64), C58(H58), C59(H59), C65(H65),
  C67(H67), C66(H66)
2.c Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C36(H36A,H36B,H36C), C54(H54A,H54B,H54C), C53(H53A,H53B,
 H53C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C49(H49A,H49B,H49C), C34(H34A,
 H34B,H34C), C35(H35A,H35B,H35C), C61(H61A,H61B,H61C), C68(H68A,H68B,H68C)
;
_shelx_res_checksum              20505
_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 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.776