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_7129783
_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            'C66 H65 N2'
_chemical_formula_weight         886.20
_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             2021-07-24
_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                102.6520(10)
_cell_angle_beta                 103.668(2)
_cell_angle_gamma                104.100(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6062(2)
_cell_length_b                   14.1110(3)
_cell_length_c                   20.1126(3)
_cell_measurement_reflns_used    15818
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      74.8720
_cell_measurement_theta_min      3.3570
_cell_volume                     2456.15(9)
_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(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.950
_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    -54.00  21.00   0.50    0.08    --  -47.57 100.00  25.00  150
  2  \w     -4.00  82.00   0.50    0.08    --   47.57-100.00 -79.00  172
  3  \w   -146.00-120.00   0.50    0.33    --  -99.00-100.00 -79.00   52
  4  \w   -106.00 -54.00   0.50    0.33    --  -99.00 100.00  25.00  104
  5  \w     59.00  88.00   0.50    0.33    --  103.25-100.00 -79.00   58
  6  \w     93.00 158.00   0.50    0.33    --  103.25 100.00  25.00  130
  7  \w   -118.00 -78.00   0.50    0.08    --  -47.57-125.00  60.00   80
  8  \w    -13.00  13.00   0.50    0.08    --  -47.57  19.00 -60.00   52
  9  \w    -27.00  27.00   0.50    0.08    --   47.57 -19.00  30.00  108
 10  \w    -11.00  45.00   0.50    0.08    --   47.57 -38.00 -90.00  112
 11  \w    -13.00  30.00   0.50    0.08    --   47.57 -19.00  90.00   86
 12  \w    -22.00  47.00   0.50    0.08    --   47.57 -38.00 -30.00  138
 13  \w    -92.00 -30.00   0.50    0.33    --  -99.00  77.00 -60.00  124
 14  \w   -168.00-130.00   0.50    0.33    --  -99.00 -62.00 126.44   76
 15  \w   -167.00 -90.00   0.50    0.33    --  -99.00 -59.00 -29.58  154
 16  \w   -116.00 -82.00   0.50    0.33    --  -99.00 -62.00 126.44   68
 17  \w   -112.00 -77.00   0.50    0.33    --  -99.00 -77.00-120.00   70
 18  \w   -125.00 -73.00   0.50    0.33    --  -99.00 143.00-136.19  104
 19  \w    -55.00 -27.00   0.50    0.33    --  -99.00  61.00 -30.00   56
 20  \w   -166.00 -83.00   0.50    0.33    --  -99.00 -76.00-109.75  166
 21  \w    -67.00 -32.00   0.50    0.33    --  -99.00 143.00-136.19   70
 22  \w   -167.00 -81.00   0.50    0.33    --  -99.00 -66.00   1.74  172
 23  \w   -112.00 -28.00   0.50    0.33    --  -99.00 125.00 -60.00  168
 24  \w     51.00  77.00   0.50    0.33    --  103.25 -94.00-180.00   52
 25  \w     31.00  74.00   0.50    0.33    --  103.25 -61.00   0.00   86
 26  \w     40.00 110.00   0.50    0.33    --  103.25-125.00 150.00  140
 27  \w     83.00 159.00   0.50    0.33    --  103.25  77.00 150.00  152
 28  \w     42.00  89.00   0.50    0.33    --  103.25 -94.00 150.00   94
 29  \w     38.00  65.00   0.50    0.33    --  103.25 -61.00  60.00   54
 30  \w     78.00 111.00   0.50    0.33    --  103.25-125.00-150.00   66
 31  \w     34.00  59.00   0.50    0.33    --  103.25-125.00-150.00   50
 32  \w     31.00 111.00   0.50    0.33    --  103.25-125.00-120.00  160
 33  \w     36.00  64.00   0.50    0.33    --  103.25 -61.00  30.00   56
 34  \w     32.00 111.00   0.50    0.33    --  103.25-125.00 120.00  158
 35  \w     71.00 106.00   0.50    0.33    --  103.25 -94.00 -30.00   70
 36  \w     80.00 105.00   0.50    0.33    --  103.25 -94.00  30.00   50
 37  \w     40.00  66.00   0.50    0.33    --  103.25 -61.00 150.00   52
;
_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      -0.1016877000
_diffrn_orient_matrix_UB_12      -0.0829874000
_diffrn_orient_matrix_UB_13      -0.0698699000
_diffrn_orient_matrix_UB_21      0.0220294000
_diffrn_orient_matrix_UB_22      -0.0835228000
_diffrn_orient_matrix_UB_23      0.0357940000
_diffrn_orient_matrix_UB_31      -0.1390783000
_diffrn_orient_matrix_UB_32      0.0016313000
_diffrn_orient_matrix_UB_33      0.0252342000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1296
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30441
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.249
_diffrn_reflns_theta_min         2.365
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40694
_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            'clear intense colourless'
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       needle
_exptl_crystal_F_000             950
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         9645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0883
_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^)+(0.0815P)^2^+1.4326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1666
_refine_ls_wR_factor_ref         0.1757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8121
_reflns_number_total             9645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00943a2.cif
_cod_data_source_block           tx6066
_cod_database_code               7129783
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHN
_reflns_odcompleteness_completeness 99.93
_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:
 C6(H6A,H6B), C22(H22A,H22B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C24(H24), C35(H35), C51(H51), C20(H20), C29(H29), C12(H12), C46(H46),
 C52(H52), C41(H41), C27(H27), C16(H16), C40(H40), C8(H8), C28(H28), C36(H36),
 C26(H26), C45(H45), C57(H57), C64(H64), C59(H59), C66(H66), C56(H56), C60(H60),
  C63(H63), C67(H67)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C32(H32A,H32B,H32C), C54(H54A,H54B,H54C), C34(H34A,H34B,
 H34C), C49(H49A,H49B,H49C), C42(H42A,H42B,H42C), C44(H44A,H44B,H44C), C53(H53A,
 H53B,H53C), C43(H43A,H43B,H43C), C61(H61A,H61B,H61C), C68(H68A,H68B,H68C)
;
_shelx_res_checksum              52465
_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 2.204
_oxdiff_exptl_absorpt_empirical_full_min 0.264