Development of unsymmetrical boron complexes bearing (iso)quinolylphenol ligands and their halogenated derivatives; crystal polymorphism for white-light-emitting properties.
Nakano, Takeo; Ichikawa, Shota; Inaba, Ryoto; Sumida, Akifumi; Hamasaki, Atom; Imoto, Hiroaki; Naka, Kensuke; Physical chemistry chemical physics : PCCP 28 (2026) 4626–4635; doi:10.1039/d5cp04402b

data_7251636
_publ_section_title
;
 Development of unsymmetrical boron complexes bearing (iso)quinolylphenol
 ligands and their halogenated derivatives; crystal polymorphism for
 white-light-emitting properties.
;
_journal_issue                   7
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              4626
_journal_page_last               4635
_journal_paper_doi               10.1039/d5cp04402b
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C15 H9 B F3 N O, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C15.5 H9 B Cl F3 N O'
_chemical_formula_weight         328.50
_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     direct
_audit_creation_date             2025-04-23
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-10-27 deposited with the CCDC.	2026-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                71.272(3)
_cell_angle_beta                 81.388(3)
_cell_angle_gamma                84.912(3)
_cell_formula_units_Z            2
_cell_length_a                   6.7344(2)
_cell_length_b                   8.3673(3)
_cell_length_c                   12.9637(5)
_cell_measurement_reflns_used    4127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.3100
_cell_measurement_theta_min      3.6260
_cell_volume                     683.37(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.923
_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     71.00 101.00   0.50    0.71    --  106.90 -99.00-180.00   60
  2  \w     41.00  73.00   0.50    0.71    --  106.90-125.00 -60.00   64
  3  \w     87.00 112.00   0.50    0.71    --  106.90-125.00 -60.00   50
  4  \w     38.00  97.00   0.50    0.71    --  106.90 -99.00 -60.00  118
  5  \w     64.00 103.00   0.50    0.71    --  106.90 -99.00 -30.00   78
  6  \w     73.00 102.00   0.50    0.71    --  106.90 -99.00  30.00   58
  7  \w     43.00  69.00   0.50    0.71    --  106.90 -99.00  30.00   52
  8  \w     60.00 101.00   0.50    0.71    --  106.90 -99.00  90.00   82
  9  \w     77.00 105.00   0.50    0.71    --  106.90 -99.00 120.00   56
 10  \w     37.00  63.00   0.50    0.71    --  106.90 -99.00 120.00   52
 11  \w     38.00  64.00   0.50    0.71    --  106.90 -85.00-162.00   52
 12  \w    -21.00  25.00   0.50    0.18    --   47.79 -19.00-120.00   92
 13  \w    -26.00  23.00   0.50    0.18    --   47.79 -19.00-180.00   98
 14  \w    -24.00  24.00   0.50    0.18    --   47.79 -19.00 -60.00   96
 15  \w      1.00  37.00   0.50    0.18    --   47.79 -38.00  90.00   72
 16  \w     39.00  66.00   0.50    0.71    --  106.90 -57.00 120.00   54
 17  \w     36.00  73.00   0.50    0.18    --   47.79 -85.00-162.00   74
 18  \w    -14.00  27.00   0.50    0.18    --   47.79 -85.00-162.00   82
 19  \w     36.00  62.00   0.50    0.71    --  106.90 -57.00-150.00   52
 20  \w    126.00 169.00   0.50    0.71    --  106.90  19.00-120.00   86
 21  \w    146.00 177.00   0.50    0.71    --  106.90 125.00-180.00   62
 22  \w     98.00 143.00   0.50    0.71    --  106.90 125.00-180.00   90
 23  \w    102.00 175.00   0.50    0.71    --  106.90 125.00 -30.00  146
 24  \w    103.00 140.00   0.50    0.71    --  106.90  85.00 -43.00   74
 25  \w   -116.00 -36.00   0.50    0.18    --  -47.79 -57.00  60.00  160
 26  \w   -161.00 -78.00   0.50    0.71    --  -91.75 -57.00 150.00  166
 27  \w   -131.00 -89.00   0.50    0.71    --  -91.75 -99.00 -60.00   84
 28  \w   -161.00 -88.00   0.50    0.71    --  -91.75 -77.00-120.00  146
 29  \w   -135.00-110.00   0.50    0.71    --  -91.75 -99.00-180.00   50
 30  \w   -120.00 -82.00   0.50    0.71    --  -91.75 -85.00-162.00   76
 31  \w   -163.00-128.00   0.50    0.71    --  -91.75 -85.00-162.00   70
 32  \w    -64.00 -20.00   0.50    0.71    --  -91.75  57.00 -30.00   88
 33  \w    -63.00 -20.00   0.50    0.71    --  -91.75  57.00 150.00   86
 34  \w    -54.00 -20.00   0.50    0.71    --  -91.75  57.00 120.00   68
 35  \w    -55.00 -19.00   0.50    0.71    --  -91.75  57.00  60.00   72
 36  \w    -65.00 -37.00   0.50    0.71    --  -91.75  57.00  30.00   56
 37  \w    -72.00 -36.00   0.50    0.18    --  -47.79  85.00 -43.00   72
 38  \w    -19.00  21.00   0.50    0.18    --  -47.79  85.00 -43.00   80
 39  \w   -115.00 -57.00   0.50    0.71    --  -91.75  85.00 -43.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1369817000
_diffrn_orient_matrix_UB_12      0.1496098000
_diffrn_orient_matrix_UB_13      -0.0258285000
_diffrn_orient_matrix_UB_21      0.0905101000
_diffrn_orient_matrix_UB_22      -0.0301724000
_diffrn_orient_matrix_UB_23      -0.1089320000
_diffrn_orient_matrix_UB_31      -0.1633307000
_diffrn_orient_matrix_UB_32      0.1207185000
_diffrn_orient_matrix_UB_33      -0.0589633000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7640
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.872
_diffrn_reflns_theta_min         3.630
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0871P)^2^+0.3267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1469
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2273
_reflns_number_total             2678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp04402b2.cif
_cod_data_source_block           250422_4_1p4f_d_autored
_cod_original_cell_volume        683.36(4)
_cod_original_formula_sum        'C15.50 H9 B Cl F3 N O'
_cod_database_code               7251636
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H9 O1 B1 N1 F3'
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.588
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) C23(0.5) H23A(0.5) H23B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20),
 C21(H21)
;
_shelx_res_checksum              8869
_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 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.705