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_7251637
_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                 94.249(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7404(11)
_cell_length_b                   7.4307(6)
_cell_length_c                   10.7770(9)
_cell_measurement_reflns_used    1511
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      76.1150
_cell_measurement_theta_min      5.6510
_cell_volume                     1257.04(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 0.996
_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    -46.00 -19.00   0.50    0.99    --  -91.75  57.00 150.00   54
  2  \w    -61.00 -26.00   0.50    0.99    --  -91.75  57.00 120.00   70
  3  \w    -65.00 -29.00   0.50    0.99    --  -91.75  57.00  90.00   72
  4  \w    -54.00 -25.00   0.50    0.99    --  -91.75  57.00  60.00   58
  5  \w    -26.00  22.00   0.50    0.25    --  -47.79  19.00  30.00   96
  6  \w    -23.00  17.00   0.50    0.25    --  -47.79  19.00-120.00   80
  7  \w    -54.00 -16.00   0.50    0.25    --  -47.79 124.00 -68.00   76
  8  \w    -78.00 -22.00   0.50    0.99    --  -91.75 125.00  60.00  112
  9  \w    -69.00 -31.00   0.50    0.99    --  -91.75 149.00  95.00   76
 10  \w     99.00 124.00   0.50    0.99    --  106.90 149.00  95.00   50
 11  \w    112.00 137.00   0.50    0.99    --  106.90 124.00 -68.00   50
 12  \w    144.00 177.00   0.50    0.99    --  106.90  57.00  90.00   66
 13  \w     93.00 138.00   0.50    0.99    --  106.90  57.00  90.00   90
 14  \w     63.00 104.00   0.50    0.99    --  106.90 -99.00-120.00   82
 15  \w     75.00 105.00   0.50    0.99    --  106.90 -99.00 -90.00   60
 16  \w     87.00 112.00   0.50    0.99    --  106.90-149.00  48.00   50
 17  \w     47.00  76.00   0.50    0.25    --   47.79-124.00-147.00   58
 18  \w     57.00  92.00   0.50    0.99    --  106.90-124.00-147.00   70
 19  \w     55.00 104.00   0.50    0.99    --  106.90 -99.00-150.00   98
 20  \w     37.00  64.00   0.50    0.99    --  106.90 -57.00 -90.00   54
 21  \w    -27.00  23.00   0.50    0.25    --   47.79 -19.00-180.00  100
 22  \w    -24.00  10.00   0.50    0.25    --   47.79 -19.00-120.00   68
 23  \w   -140.00-115.00   0.50    0.99    --  -91.75 -99.00-180.00   50
 24  \w   -159.00 -75.00   0.50    0.99    --  -91.75-124.00-147.00  168
 25  \w    -88.00 -63.00   0.50    0.25    --  -47.79-149.00  48.00   50
 26  \w   -127.00-102.00   0.50    0.99    --  -91.75-149.00  48.00   50
;
_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      -0.0878938000
_diffrn_orient_matrix_UB_12      0.0630498000
_diffrn_orient_matrix_UB_13      0.0371863000
_diffrn_orient_matrix_UB_21      0.0308626000
_diffrn_orient_matrix_UB_22      0.1966437000
_diffrn_orient_matrix_UB_23      0.0003881000
_diffrn_orient_matrix_UB_31      -0.0310675000
_diffrn_orient_matrix_UB_32      0.0179708000
_diffrn_orient_matrix_UB_33      -0.1383867000
_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  0.0390
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4069
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.071
_diffrn_reflns_theta_min         5.637
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69380
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0275P)^2^+0.9918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1311
_reflns_Friedel_coverage         0.000
_reflns_number_gt                942
_reflns_number_total             1228
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp04402b2.cif
_cod_data_source_block           250529_3_1p4cl_b_orange_3rd_autored
_cod_database_code               7251637
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C15 H9 B1 N1 O1 Cl1 F2'
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.406
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: Cl11(0.5) N2(0.5) O10(0.5) C6(0.5) H6(0.5) C5(0.5) H5(0.5) C4(0.5)
 C9(0.5) C8(0.5) H8(0.5) C7(0.5) C12(0.5) H12(0.5) C15(0.5) C16(0.5) H16(0.5)
 C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5) C14(0.5) C13(0.5)
 H13(0.5) F20(0.5) F21(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C8(H8), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19),
 C13(H13)
;
_shelx_res_checksum              11680
_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 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.505