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_7251634
_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 Cl F2 N O'
_chemical_formula_sum            'C15 H9 B Cl F2 N O'
_chemical_formula_weight         303.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2026-01-19
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2026-01-21 deposited with the CCDC.	2026-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.246(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7169(13)
_cell_length_b                   7.4273(4)
_cell_length_c                   10.7772(10)
_cell_measurement_reflns_used    2226
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      73.1380
_cell_measurement_theta_min      5.6080
_cell_volume                     1254.61(17)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.937
_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   -112.00 -66.00   0.50    0.45    --  -47.54-137.00 146.00   92
  2  \w    -81.00 -56.00   0.50    0.45    --  -47.54 137.00-150.00   50
  3  \w   -113.00 -69.00   0.50    0.45    --  -47.54-133.00 -36.00   88
  4  \w    -78.00 -53.00   0.50    0.45    --  -47.54 133.00  32.00   50
  5  \w     43.00  68.00   0.50    0.45    --   47.54-133.00 -36.00   50
  6  \w     51.00  98.00   0.50    0.45    --   47.54-137.00 146.00   94
  7  \w    -84.00 -34.00   0.50    1.79    --  -91.75 133.00  32.00  100
  8  \w    -94.00 -68.00   0.50    1.79    --  -91.75-137.00 146.00   52
  9  \w     90.00 158.00   0.50    1.79    --  106.90 133.00  32.00  136
 10  \w     89.00 115.00   0.50    1.79    --  106.90-133.00 -36.00   52
 11  \w     88.00 131.00   0.50    1.79    --  106.90 137.00-150.00   86
 12  \w     79.00 115.00   0.50    1.79    --  106.90-137.00 146.00   72
 13  \w    -19.00  27.00   0.50    0.45    --  -47.54  19.00-120.00   92
 14  \w    -24.00  27.00   0.50    0.45    --  -47.54  19.00  30.00  102
 15  \w    -15.00  28.00   0.50    0.45    --  -47.54  19.00 -30.00   86
 16  \w    -17.00  25.00   0.50    0.45    --   47.54 -19.00  30.00   84
 17  \w    -26.00   9.00   0.50    0.45    --   47.54 -19.00-180.00   70
 18  \w   -160.00-108.00   0.50    1.79    --  -91.75 -57.00 150.00  104
 19  \w   -162.00-124.00   0.50    1.79    --  -91.75 -57.00  30.00   76
 20  \w    -80.00 -55.00   0.50    1.79    --  -91.75 125.00-180.00   50
 21  \w   -119.00 -86.00   0.50    1.79    --  -91.75 -57.00  30.00   66
 22  \w   -137.00 -99.00   0.50    1.79    --  -91.75 -99.00-180.00   76
 23  \w    -64.00 -19.00   0.50    1.79    --  -91.75  57.00-180.00   90
 24  \w    -55.00 -29.00   0.50    1.79    --  -91.75  57.00  30.00   52
 25  \w    -50.00 -20.00   0.50    1.79    --  -91.75  57.00   0.00   60
 26  \w     41.00  66.00   0.50    1.79    --  106.90 -77.00 120.00   50
 27  \w     71.00 105.00   0.50    1.79    --  106.90 -99.00-180.00   68
 28  \w     39.00  64.00   0.50    1.79    --  106.90 -57.00 -30.00   50
 29  \w     36.00  62.00   0.50    1.79    --  106.90 -99.00-180.00   52
 30  \w     74.00 104.00   0.50    1.79    --  106.90 -99.00 -30.00   60
 31  \w     37.00  69.00   0.50    1.79    --  106.90 -99.00 -30.00   64
 32  \w     78.00 103.00   0.50    1.79    --  106.90 -77.00 -30.00   50
 33  \w     70.00 109.00   0.50    1.79    --  106.90-125.00  90.00   78
 34  \w    153.00 178.00   0.50    1.79    --  106.90  38.00-150.00   50
 35  \w     40.00  66.00   0.50    1.79    --  106.90-125.00  90.00   52
 36  \w     95.00 142.00   0.50    1.79    --  106.90  38.00-150.00   94
 37  \w     96.00 122.00   0.50    1.79    --  106.90  19.00  30.00   52
 38  \w    140.00 177.00   0.50    1.79    --  106.90  19.00  30.00   74
 39  \w     35.00  61.00   0.50    1.79    --  106.90 -57.00-180.00   52
 40  \w     36.00  62.00   0.50    1.79    --  106.90 -57.00-150.00   52
 41  \w     48.00  98.00   0.50    1.79    --  106.90 -99.00 -60.00  100
 42  \w     35.00  60.00   0.50    1.79    --  106.90 -57.00  90.00   50
 43  \w     69.00 105.00   0.50    1.79    --  106.90 -99.00 150.00   72
;
_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      -0.0047891000
_diffrn_orient_matrix_UB_12      -0.0083732000
_diffrn_orient_matrix_UB_13      -0.1431746000
_diffrn_orient_matrix_UB_21      0.0780064000
_diffrn_orient_matrix_UB_22      -0.1264037000
_diffrn_orient_matrix_UB_23      0.0060208000
_diffrn_orient_matrix_UB_31      -0.0595577000
_diffrn_orient_matrix_UB_32      -0.1643330000
_diffrn_orient_matrix_UB_33      0.0022212000
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5289
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.875
_diffrn_reflns_theta_min         5.645
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79843
_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    1.607
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0353P)^2^+1.2087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                946
_reflns_number_total             1239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp04402b2.cif
_cod_data_source_block           250520_1_1p4clb_1st_blue_autored
_cod_database_code               7251634
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C15 H9 B1 N1 O1 Cl1 F2'
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.567
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C7(0.5) H7(0.5) C10(0.5) H10(0.5) C9(0.5) H9(0.5) C8(0.5) H8(0.5)
 C4(0.5) H4(0.5) C3(0.5) N2(0.5) C11(0.5) C6(0.5) C5(0.5) H5(0.5) O18(0.5)
 Cl19(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) C16(0.5) H16(0.5)
 C17(0.5) C12(0.5) F20(0.5) F21(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C9(H9), C8(H8), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16)
;
_shelx_res_checksum              90309
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.650