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_7251638
_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             2025-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-10-27 deposited with the CCDC.	2026-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.954(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0315(4)
_cell_length_b                   10.9383(4)
_cell_length_c                   18.9864(6)
_cell_measurement_reflns_used    4008
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5010
_cell_measurement_theta_min      4.6230
_cell_volume                     2498.34(15)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.939
_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    -59.00 -19.00   0.50    1.37    --  -91.75  57.00 150.00   80
  2  \w    -61.00 -35.00   0.50    1.37    --  -91.75  57.00  90.00   52
  3  \w   -164.00 -80.00   0.50    1.37    --  -91.75 -32.00 -11.00  168
  4  \w   -117.00 -35.00   0.50    0.34    --  -47.79 -32.00 -11.00  164
  5  \w    -63.00 -23.00   0.50    1.37    --  -91.75  57.00   0.00   80
  6  \w    -57.00 -24.00   0.50    1.37    --  -91.75  57.00 -30.00   66
  7  \w    -64.00 -20.00   0.50    1.37    --  -91.75  57.00 -60.00   88
  8  \w    -59.00 -20.00   0.50    1.37    --  -91.75  57.00-120.00   78
  9  \w    -24.00  27.00   0.50    0.34    --  -47.79  19.00 -60.00  102
 10  \w    -29.00  27.00   0.50    0.34    --  -47.79  32.00 147.00  112
 11  \w     47.00  72.00   0.50    0.34    --   47.79-125.00  90.00   50
 12  \w     73.00  98.00   0.50    1.37    --  106.90 -99.00-180.00   50
 13  \w     74.00 104.00   0.50    1.37    --  106.90 -77.00-180.00   60
 14  \w     35.00  60.00   0.50    1.37    --  106.90 -57.00-180.00   50
 15  \w     40.00  67.00   0.50    1.37    --  106.90 -77.00-180.00   54
 16  \w     35.00  61.00   0.50    1.37    --  106.90 -57.00-120.00   52
 17  \w    -17.00  25.00   0.50    0.34    --   47.79 -32.00 -11.00   84
 18  \w     37.00  64.00   0.50    1.37    --  106.90 -57.00   0.00   54
 19  \w     35.00  66.00   0.50    1.37    --  106.90 -57.00  60.00   62
 20  \w     36.00  62.00   0.50    1.37    --  106.90 -57.00  90.00   52
 21  \w    112.00 149.00   0.50    1.37    --  106.90  32.00 147.00   74
 22  \w     59.00 123.00   0.50    0.34    --   47.79  32.00 147.00  128
 23  \w    102.00 162.00   0.50    1.37    --  106.90  38.00-120.00  120
 24  \w     98.00 159.00   0.50    1.37    --  106.90 125.00-180.00  122
;
_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      0.0459103000
_diffrn_orient_matrix_UB_12      -0.0218508000
_diffrn_orient_matrix_UB_13      0.0752743000
_diffrn_orient_matrix_UB_21      0.1073954000
_diffrn_orient_matrix_UB_22      -0.0539627000
_diffrn_orient_matrix_UB_23      -0.0304463000
_diffrn_orient_matrix_UB_31      0.0527761000
_diffrn_orient_matrix_UB_32      0.1280383000
_diffrn_orient_matrix_UB_33      -0.0001550000
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8213
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.600
_diffrn_reflns_theta_min         4.659
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49070
_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    1.614
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0921P)^2^+3.2091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2179
_reflns_number_total             2470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp04402b2.cif
_cod_data_source_block           250520_3_1p3cl_2nd_autored
_cod_database_code               7251638
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H9 B1 N1 O1 Cl1 F2'
_shelx_estimated_absorpt_t_max   0.822
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C17(H17), C11(H11), C8(H8), C16(H16), C15(H15), C6(H6),
 C7(H7)
;
_shelx_res_checksum              97982
_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 1.611
_oxdiff_exptl_absorpt_empirical_full_min 0.521