Selective recognition between aromatics and aliphatics by cage-shaped borates supported by a machine learning approach.
Tsutsui, Yuya; Yanaka, Issei; Takeda, Kazuhiro; Kondo, Masaru; Takizawa, Shinobu; Kojima, Ryosuke; Konishi, Akihito; Yasuda, Makoto; Organic & biomolecular chemistry 22 (2024) 4283–4291; doi:10.1039/d4ob00408f

data_7159882
_publ_section_title
;
 Selective recognition between aromatics and aliphatics by cage-shaped
 borates supported by a machine learning approach.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4283
_journal_page_last               4291
_journal_paper_doi               10.1039/d4ob00408f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C48 H28 B Br2 N O6, C H Cl3'
_chemical_formula_sum            'C49 H29 B Br2 Cl3 N O6'
_chemical_formula_weight         1004.71
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-27 deposited with the CCDC.	2024-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.39030(10)
_cell_length_b                   32.0048(2)
_cell_length_c                   10.89300(10)
_cell_measurement_reflns_used    29084
_cell_measurement_temperature    190
_cell_measurement_theta_max      74.3070
_cell_measurement_theta_min      3.6450
_cell_volume                     4203.25(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      190
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -60.00 -12.00   0.50    0.79    --  -42.93  71.00-105.00   96
  2  \w    -76.00 -34.00   0.50    3.67    -- -106.00  77.00-180.00   84
  3  \w    -61.00 -32.00   0.50    3.67    -- -106.00  77.00-120.00   58
  4  \w    -53.00 -28.00   0.50    3.67    -- -106.00  19.00-150.00   50
  5  \w    -88.00 -51.00   0.50    3.67    -- -106.00  37.00-120.00   74
  6  \w    -87.00 -37.00   0.50    3.67    -- -106.00   0.00 -90.00  100
  7  \w   -106.00 -81.00   0.50    3.67    -- -106.00  71.00-105.00   50
  8  \w   -110.00 -84.00   0.50    3.67    -- -106.00  80.00-115.13   52
  9  \w   -126.00-100.00   0.50    3.67    -- -106.00  77.00-180.00   52
 10  \w   -135.00 -79.00   0.50    3.67    -- -106.00  77.00-120.00  112
 11  \w   -116.00 -51.00   0.50    3.67    -- -106.00 125.00 -90.00  130
 12  \w    -68.00 -43.00   0.50    3.67    -- -106.00 125.00 -30.00   50
 13  \w    -94.00 -36.00   0.50    3.67    -- -106.00  77.00  60.00  116
 14  \w    -95.00 -69.00   0.50    3.67    -- -106.00  57.00  30.00   52
 15  \w   -121.00 -85.00   0.50    3.67    -- -106.00 -19.00  90.00   72
 16  \w   -106.00 -79.00   0.50    3.67    -- -106.00 -77.00 150.00   54
 17  \w   -103.00 -78.00   0.50    3.67    -- -106.00 -77.00 120.00   50
 18  \w   -102.00 -71.00   0.50    3.67    -- -106.00-125.00 120.00   62
 19  \w   -117.00 -86.00   0.50    3.67    -- -106.00 -96.00  28.76   62
 20  \w   -124.00 -94.00   0.50    3.67    -- -106.00 -57.00 -60.00   60
 21  \w   -119.00 -89.00   0.50    3.67    -- -106.00 -67.00 -85.80   60
 22  \w   -124.00 -91.00   0.50    3.67    -- -106.00 -77.00-150.00   66
 23  \w   -115.00 -71.00   0.50    0.79    --  -42.93-125.00-150.00   88
 24  \w   -149.00-123.00   0.50    3.67    -- -106.00 -19.00   0.00   52
 25  \w   -166.00-140.00   0.50    3.67    -- -106.00 -57.00 -60.00   52
 26  \w   -151.00-125.00   0.50    3.67    -- -106.00 -67.00 -85.80   52
 27  \w   -174.00 -68.00   0.50    3.67    -- -106.00  -9.00 -57.84  212
 28  \w   -135.00 -39.00   0.50    3.67    -- -106.00  77.00  30.00  192
 29  \w   -119.00 -42.00   0.50    3.67    -- -106.00  77.00 -30.00  154
 30  \w   -124.00 -45.00   0.50    3.67    -- -106.00  60.00 -59.10  158
 31  \w   -100.00 -16.00   0.50    0.79    --  -42.93 -71.00 124.00  168
 32  \w     59.00  96.00   0.50    0.79    --   42.93  71.00-105.00   74
 33  \w     76.00 101.00   0.50    3.67    --   76.50  71.00-105.00   50
 34  \w     22.00 117.00   0.50    0.79    --   42.93  57.00-150.00  190
 35  \w     15.00  43.00   0.50    0.79    --   42.93 -71.00 124.00   56
 36  \w     18.00  43.00   0.50    3.67    --   76.50 -71.00 124.00   50
 37  \w     73.00 111.00   0.50    0.79    --   42.93 125.00 120.00   76
 38  \w   -117.00 -91.00   0.50    3.67    -- -106.00 -19.00 150.00   52
 39  \w   -123.00 -92.00   0.50    3.67    -- -106.00 -71.00 124.00   62
 40  \w   -120.00 -95.00   0.50    3.67    -- -106.00 -57.00 120.00   50
 41  \w   -146.00-121.00   0.50    3.67    -- -106.00-125.00 120.00   50
 42  \w   -134.00-108.00   0.50    3.67    -- -106.00-125.00  90.00   52
 43  \w   -139.00-113.00   0.50    3.67    -- -106.00-125.00  30.00   52
 44  \w   -166.00-135.00   0.50    3.67    -- -106.00 -96.00  28.76   62
 45  \w   -158.00-122.00   0.50    3.67    -- -106.00 -77.00 150.00   72
 46  \w   -171.00-113.00   0.50    3.67    -- -106.00 -37.00 150.00  116
 47  \w   -175.00-150.00   0.50    3.67    -- -106.00 -19.00 150.00   50
 48  \w   -120.00 -80.00   0.50    3.67    -- -106.00  37.00 -60.00   80
 49  \w   -163.00-138.00   0.50    3.67    -- -106.00   0.00 -90.00   50
 50  \w   -176.00-122.00   0.50    3.67    -- -106.00 -99.00 -90.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0037212000
_diffrn_orient_matrix_UB_12      0.0379967000
_diffrn_orient_matrix_UB_13      -0.0858595000
_diffrn_orient_matrix_UB_21      -0.1256851000
_diffrn_orient_matrix_UB_22      0.0063680000
_diffrn_orient_matrix_UB_23      -0.0155909000
_diffrn_orient_matrix_UB_31      0.0227083000
_diffrn_orient_matrix_UB_32      0.0288751000
_diffrn_orient_matrix_UB_33      0.1161890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            54661
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.276
_diffrn_reflns_theta_min         3.666
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.099
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         8499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0525P)^2^+1.6670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7796
_reflns_number_total             8499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00408f2.cif
_cod_data_source_block           1121
_cod_depositor_comments
'Adding full bibliography for 7159882--7159883.cif.'
_cod_database_code               7159882
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 O B Br Cl'
_chemical_oxdiff_usercomment     CHCl3/hexane
_reflns_odcompleteness_completeness 98.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(Br1)=Sof(Br2)=1-FVAR(1)
 Sof(Br01)=Sof(Br02)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C49(H49)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C21(H21), C44(H44), C5(H5), C48(H48), C19(H19), C6(H6), C13(H13),
 C46(H46), C17(H17), C29(H29), C18(H18), C11(H11), C37(H37), C12(H12), C26(H26),
  C23(H23), C24(H24), C42(H42), C25(H25), C34(H34), C41(H41), C31(H31),
 C40(H40), C39(H39), C33(H33), C32(H32)
;
_shelx_res_checksum              10449
_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 2.571
_oxdiff_exptl_absorpt_empirical_full_min 0.605