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_7129782
_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            'C65 H65 N3'
_chemical_formula_weight         888.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 98.4260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.18180(10)
_cell_length_b                   39.3842(4)
_cell_length_c                   9.47760(10)
_cell_measurement_reflns_used    25605
_cell_measurement_temperature    169.97(12)
_cell_measurement_theta_max      74.9150
_cell_measurement_theta_min      3.3830
_cell_volume                     4867.23(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      169.97(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_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   -119.00 -85.00   0.50    0.05    --  -47.70-129.00  92.00   68
  2  \w   -111.00 -64.00   0.50    0.05    --  -47.70-141.00 -79.00   94
  3  \w    -80.00 -54.00   0.50    0.05    --  -47.70 129.00 166.00   52
  4  \w     52.00  97.00   0.50    0.05    --   47.70-129.00  92.00   90
  5  \w     66.00  91.00   0.50    0.05    --   47.70-141.00 -79.00   50
  6  \w   -144.00-119.00   0.50    0.20    --  -99.00-129.00  92.00   50
  7  \w   -115.00 -27.00   0.50    0.20    --  -99.00 129.00 166.00  176
  8  \w    -99.00 -74.00   0.50    0.20    --  -99.00 141.00 -21.00   50
  9  \w     78.00 169.00   0.50    0.20    --  103.25 129.00 166.00  182
 10  \w     72.00 112.00   0.50    0.20    --  103.25-129.00  92.00   80
 11  \w     31.00  93.00   0.50    0.20    --  103.25-141.00 -79.00  124
 12  \w    119.00 166.00   0.50    0.20    --  103.25 141.00 -21.00   94
 13  \w    -19.00  28.00   0.50    0.05    --  -47.70  19.00 120.00   94
 14  \w    -22.00  28.00   0.50    0.05    --  -47.70  19.00-180.00  100
 15  \w   -117.00 -86.00   0.50    0.05    --  -47.70-125.00-150.00   62
 16  \w    -27.00  29.00   0.50    0.05    --   47.70 -19.00   0.00  112
 17  \w   -112.00 -49.00   0.50    0.20    --  -99.00 125.00  90.00  126
 18  \w    -68.00 -27.00   0.50    0.20    --  -99.00  61.00 150.00   82
 19  \w   -161.00-126.00   0.50    0.20    --  -99.00 -30.00 150.00   70
 20  \w    -68.00 -42.00   0.50    0.20    --  -99.00  61.00 -60.00   52
 21  \w   -168.00-102.00   0.50    0.20    --  -99.00 -30.00 -90.00  132
 22  \w   -118.00 -86.00   0.50    0.20    --  -99.00 -30.00 150.00   64
 23  \w    120.00 169.00   0.50    0.20    --  103.25 125.00 120.00   98
 24  \w     82.00 110.00   0.50    0.20    --  103.25 125.00 120.00   56
 25  \w     31.00 101.00   0.50    0.20    --  103.25 -94.00  90.00  140
 26  \w     78.00 106.00   0.50    0.20    --  103.25 -94.00 150.00   56
 27  \w     33.00  73.00   0.50    0.20    --  103.25 -94.00 150.00   80
 28  \w     82.00 107.00   0.50    0.20    --  103.25  77.00-120.00   50
 29  \w     32.00  74.00   0.50    0.20    --  103.25 -61.00 120.00   84
 30  \w     91.00 168.00   0.50    0.20    --  103.25  45.00  90.00  154
;
_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      -0.0105300000
_diffrn_orient_matrix_UB_12      0.0247542000
_diffrn_orient_matrix_UB_13      0.1229010000
_diffrn_orient_matrix_UB_21      -0.0022555000
_diffrn_orient_matrix_UB_22      -0.0302350000
_diffrn_orient_matrix_UB_23      0.1026479000
_diffrn_orient_matrix_UB_31      0.1176253000
_diffrn_orient_matrix_UB_32      0.0016231000
_diffrn_orient_matrix_UB_33      0.0372484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            45750
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.253
_diffrn_reflns_theta_min         2.244
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71251
_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    1.212
_exptl_crystal_description       needle
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         9670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0545P)^2^+1.4574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8846
_reflns_number_total             9670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00943a2.cif
_cod_data_source_block           tx6067
_cod_database_code               7129782
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHN
_reflns_odcompleteness_completeness 99.67
_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:
 C23(H23A,H23B), C13(H13A,H13B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C38(H38), C15(H15), C39(H39), C25(H25), C40(H40), C29(H29), C7(H7),
 C41(H41), C11(H11), C30(H30), C37(H37), C42(H42), C2(H2), C3(H3), C33(H33),
 C46(H46), C59(H59), C47(H47), C56(H56), C58(H58), C60(H60), C63(H63), C65(H65),
  C67(H67), C66(H66)
2.c Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C54(H54A,H54B,H54C), C53(H53A,H53B,H53C), C36(H36A,H36B,
 H36C), C34(H34A,H34B,H34C), C50(H50A,H50B,H50C), C49(H49A,H49B,H49C), C35(H35A,
 H35B,H35C), C48(H48A,H48B,H48C), C61(H61A,H61B,H61C), C68(H68A,H68B,H68C)
;
_shelx_res_checksum              16138
_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 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.528