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_7159883
_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         'C H2 Cl2, C60 H36 B N O6'
_chemical_formula_sum            'C61 H38 B Cl2 N O6'
_chemical_formula_weight         962.63
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-02
_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                87.3930(10)
_cell_angle_beta                 77.1020(10)
_cell_angle_gamma                80.1780(10)
_cell_formula_units_Z            4
_cell_length_a                   14.3033(2)
_cell_length_b                   16.7148(2)
_cell_length_c                   20.3372(2)
_cell_measurement_reflns_used    47440
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.0140
_cell_measurement_theta_min      3.4770
_cell_volume                     4669.87(10)
_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      123
_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 0.990
_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     38.00  65.00   0.50    0.11    --   42.80 -78.00  48.00   54
  2  \w     42.00  68.00   0.50    0.45    --   76.50 -78.00  48.00   52
  3  \w     -3.00  22.00   0.50    0.11    --   42.80 -78.00  48.00   50
  4  \w    -11.00  35.00   0.50    0.11    --  -42.80  37.00  30.00   92
  5  \w    -26.00  -1.00   0.50    0.11    --  -42.80  78.00 173.00   50
  6  \w    -68.00 -42.00   0.50    0.45    -- -106.00 125.00  90.00   52
  7  \w    -95.00 -69.00   0.50    0.45    -- -106.00  78.00 173.00   52
  8  \w   -106.00 -59.00   0.50    0.45    -- -106.00 123.00 137.40   94
  9  \w    -87.00 -58.00   0.50    0.45    -- -106.00 138.00  93.14   58
 10  \w    -99.00 -73.00   0.50    0.45    -- -106.00  85.00  46.14   52
 11  \w    -76.00 -33.00   0.50    0.45    -- -106.00  57.00  60.00   86
 12  \w    -90.00 -64.00   0.50    0.45    -- -106.00  57.00  30.00   52
 13  \w    -67.00 -41.00   0.50    0.45    -- -106.00  37.00 -30.00   52
 14  \w    -52.00 -26.00   0.50    0.45    -- -106.00  19.00 -90.00   52
 15  \w    -59.00 -33.00   0.50    0.45    -- -106.00  89.00-167.03   52
 16  \w    -76.00 -51.00   0.50    0.45    -- -106.00 125.00-180.00   50
 17  \w    -94.00 -51.00   0.50    0.45    -- -106.00  77.00-150.00   86
 18  \w    -86.00 -60.00   0.50    0.45    -- -106.00  78.00 -99.45   52
 19  \w   -103.00 -77.00   0.50    0.45    -- -106.00 125.00-180.00   52
 20  \w   -107.00 -32.00   0.50    0.45    -- -106.00 125.00-150.00  150
 21  \w   -107.00 -81.00   0.50    0.45    -- -106.00  77.00   0.00   52
 22  \w   -111.00 -85.00   0.50    0.45    -- -106.00  77.00  30.00   52
 23  \w   -103.00 -64.00   0.50    0.45    -- -106.00  86.00  79.52   78
 24  \w    -97.00 -71.00   0.50    0.45    -- -106.00  68.00  84.95   52
 25  \w   -115.00 -64.00   0.50    0.45    -- -106.00 125.00 150.00  102
 26  \w   -118.00 -92.00   0.50    0.45    -- -106.00  61.00  69.52   52
 27  \w   -119.00 -93.00   0.50    0.45    -- -106.00  65.00  30.68   52
 28  \w   -112.00 -87.00   0.50    0.45    -- -106.00  57.00   0.00   50
 29  \w   -110.00 -52.00   0.50    0.45    -- -106.00 100.00 -42.93  116
 30  \w   -104.00 -78.00   0.50    0.45    -- -106.00 125.00 -90.00   52
 31  \w   -116.00 -60.00   0.50    0.45    -- -106.00 125.00 -60.00  112
 32  \w   -117.00 -53.00   0.50    0.45    -- -106.00 125.00 -30.00  128
 33  \w    -64.00 -15.00   0.50    0.11    --  -42.80  37.00  30.00   98
 34  \w    -98.00 -14.00   0.50    0.11    --  -42.80 -78.00  48.00  168
 35  \w     13.00 115.00   0.50    0.11    --   42.80  78.00 173.00  204
 36  \w     75.00 100.00   0.50    0.45    --   76.50  78.00 173.00   50
 37  \w     72.00 120.00   0.50    0.45    --   76.50 125.00  90.00   96
 38  \w     72.00 117.00   0.50    0.11    --   42.80 125.00  60.00   90
 39  \w     71.00 116.00   0.50    0.11    --   42.80 125.00-150.00   90
 40  \w    109.00 149.00   0.50    0.45    --   76.50 125.00-180.00   80
 41  \w    -91.00 -21.00   0.50    0.11    --  -42.80 125.00 150.00  140
 42  \w   -115.00 -89.00   0.50    0.45    -- -106.00 125.00   0.00   52
 43  \w   -114.00 -68.00   0.50    0.45    -- -106.00 125.00  30.00   92
 44  \w   -124.00 -99.00   0.50    0.45    -- -106.00  79.00 -50.07   50
 45  \w   -125.00 -99.00   0.50    0.45    -- -106.00  77.00 -90.00   52
 46  \w   -115.00 -53.00   0.50    0.45    -- -106.00  57.00-150.00  124
 47  \w   -105.00 -79.00   0.50    0.45    -- -106.00 -22.00-105.19   52
 48  \w   -115.00 -85.00   0.50    0.45    -- -106.00 -57.00 -60.00   60
 49  \w   -135.00 -97.00   0.50    0.45    -- -106.00 -37.00 -30.00   76
 50  \w   -128.00 -87.00   0.50    0.45    -- -106.00 -99.00  30.00   82
 51  \w    -99.00 -72.00   0.50    0.45    -- -106.00-125.00 -30.00   54
 52  \w   -132.00-106.00   0.50    0.45    -- -106.00 -99.00  60.00   52
 53  \w   -130.00-104.00   0.50    0.45    -- -106.00 -99.00 120.00   52
 54  \w   -108.00 -82.00   0.50    0.45    -- -106.00-125.00 144.09   52
 55  \w   -108.00 -70.00   0.50    0.45    -- -106.00-125.00 150.00   76
 56  \w   -119.00 -94.00   0.50    0.45    -- -106.00 -37.00 120.00   50
 57  \w   -132.00-103.00   0.50    0.45    -- -106.00 -19.00  90.00   58
 58  \w   -128.00 -31.00   0.50    0.45    -- -106.00  42.00 163.08  194
 59  \w   -125.00 -96.00   0.50    0.45    -- -106.00 138.00  93.14   58
 60  \w   -129.00 -82.00   0.50    0.45    -- -106.00 141.00 166.81   94
 61  \w   -125.00 -70.00   0.50    0.45    -- -106.00 136.00  53.34  110
 62  \w   -125.00 -73.00   0.50    0.45    -- -106.00 136.00  17.65  104
 63  \w   -129.00-101.00   0.50    0.45    -- -106.00 142.00 -87.92   56
 64  \w   -116.00 -74.00   0.50    0.45    -- -106.00 125.00-120.00   84
 65  \w   -106.00 -80.00   0.50    0.45    -- -106.00  89.00-167.03   52
 66  \w   -111.00 -86.00   0.50    0.45    -- -106.00  44.00-138.61   50
 67  \w   -111.00 -64.00   0.50    0.45    -- -106.00  19.00 -90.00   94
 68  \w   -127.00 -84.00   0.50    0.45    -- -106.00 -77.00-180.00   86
 69  \w   -150.00-124.00   0.50    0.45    -- -106.00 -99.00-180.00   52
 70  \w   -177.00-107.00   0.50    0.45    -- -106.00 -37.00 -90.00  140
 71  \w   -132.00 -83.00   0.50    0.45    -- -106.00 -36.00 -21.58   98
 72  \w   -126.00 -77.00   0.50    0.45    -- -106.00  37.00  60.00   98
 73  \w   -120.00 -88.00   0.50    0.45    -- -106.00  57.00  90.00   64
 74  \w   -128.00 -59.00   0.50    0.45    -- -106.00  57.00 120.00  138
 75  \w   -126.00-101.00   0.50    0.45    -- -106.00  85.00  46.14   50
 76  \w   -151.00-102.00   0.50    0.45    -- -106.00 -19.00   0.00   98
 77  \w   -145.00-120.00   0.50    0.45    -- -106.00 -37.00   0.00   50
 78  \w   -150.00 -94.00   0.50    0.45    -- -106.00 -78.00  48.00  112
 79  \w   -134.00-105.00   0.50    0.45    -- -106.00 -99.00 150.00   58
 80  \w   -162.00-137.00   0.50    0.45    -- -106.00-125.00 144.09   50
 81  \w   -161.00-135.00   0.50    0.45    -- -106.00 -99.00 120.00   52
 82  \w   -177.00 -84.00   0.50    0.45    -- -106.00 -74.00 127.09  186
 83  \w   -168.00-143.00   0.50    0.45    -- -106.00 -37.00 120.00   50
 84  \w   -175.00-105.00   0.50    0.45    -- -106.00 -57.00  60.00  140
 85  \w   -172.00-116.00   0.50    0.45    -- -106.00-125.00 120.00  112
 86  \w   -163.00-138.00   0.50    0.45    -- -106.00 -99.00  30.00   50
 87  \w   -165.00-140.00   0.50    0.45    -- -106.00 -37.00 -30.00   50
 88  \w   -165.00-129.00   0.50    0.45    -- -106.00 -57.00  90.00   72
 89  \w   -153.00 -83.00   0.50    0.45    -- -106.00 -37.00 150.00  140
 90  \w   -174.00-126.00   0.50    0.45    -- -106.00 -99.00  90.00   96
 91  \w   -173.00-121.00   0.50    0.45    -- -106.00-125.00 -60.00  104
 92  \w   -175.00 -84.00   0.50    0.45    -- -106.00 -37.00-180.00  182
 93  \w   -135.00-109.00   0.50    0.45    -- -106.00  77.00-150.00   52
 94  \w   -127.00-102.00   0.50    0.45    -- -106.00  86.00-176.63   50
 95  \w   -128.00 -84.00   0.50    0.45    -- -106.00 141.00-149.65   88
 96  \w   -123.00 -98.00   0.50    0.45    -- -106.00  78.00 -99.45   50
 97  \w   -160.00-135.00   0.50    0.45    -- -106.00 -19.00-150.00   50
;
_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      -0.0223095000
_diffrn_orient_matrix_UB_12      -0.0796545000
_diffrn_orient_matrix_UB_13      -0.0234805000
_diffrn_orient_matrix_UB_21      -0.0860531000
_diffrn_orient_matrix_UB_22      0.0018940000
_diffrn_orient_matrix_UB_23      0.0612462000
_diffrn_orient_matrix_UB_31      -0.0681674000
_diffrn_orient_matrix_UB_32      0.0490058000
_diffrn_orient_matrix_UB_33      -0.0416773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            115522
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.483
_diffrn_reflns_theta_min         3.476
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85750
_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 light colourless'
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.159
_refine_diff_density_max         0.322
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1307
_refine_ls_number_reflns         18886
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0882P)^2^+3.0901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16252
_reflns_number_total             18886
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00408f2.cif
_cod_data_source_block           naphtho
_cod_depositor_comments
'Adding full bibliography for 7159882--7159883.cif.'
_cod_database_code               7159883
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 B O N Cl'
_chemical_oxdiff_usercomment     CH2CL2/hexane
_reflns_odcompleteness_completeness 98.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Cl14 \\sim Cl4 \\sim Cl3: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Cl0A \\sim Cl1 \\sim Cl2 \\sim Cl1A: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(Cl4) \\sim Ueq, Uanis(Cl14) \\sim Ueq, Uanis(Cl3) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(Cl1) \\sim Ueq, Uanis(Cl0A) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl1A)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Others
 Sof(H12C)=Sof(H12D)=Sof(H12G)=Sof(H12H)=Sof(Cl1A)=Sof(Cl0A)=Sof(Cl14)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl4)=Sof(H12A)=Sof(H12B)=Sof(H12E)=Sof(H12F)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C61(H61), C1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C121(H12A,H12B), C121(H12C,H12D), C122(H12E,H12F), C122(H12G,H12H)
4.c Aromatic/amide H refined with riding coordinates:
 C33(H33), C56(H56), C120(H120), C105(H105), C65(H65), C93(H93), C81(H81),
 C11(H11), C77(H77), C79(H79), C45(H45), C66(H66), C13(H13), C21(H21), C17(H17),
  C19(H19), C42(H42), C7(H7), C57(H57), C18(H18), C36(H36), C78(H78), C67(H67),
 C90(H90), C12(H12), C73(H73), C41(H41), C6(H6), C5(H5), C89(H89), C119(H119),
 C37(H37), C60(H60), C108(H108), C116(H116), C96(H96), C24(H24), C118(H118),
 C39(H39), C84(H84), C38(H38), C72(H72), C87(H87), C101(H101), C97(H97),
 C71(H71), C99(H99), C114(H114), C30(H30), C48(H48), C113(H113), C27(H27),
 C117(H117), C58(H58), C86(H86), C29(H29), C85(H85), C111(H111), C110(H110),
 C109(H109), C54(H54), C25(H25), C102(H102), C98(H98), C59(H59), C49(H49),
 C26(H26), C50(H50), C51(H51), C53(H53)
;
_shelx_res_checksum              35168
_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 3.405
_oxdiff_exptl_absorpt_empirical_full_min 0.496