Design of Heavy-Atom Free Dipyridomethene Boron Complexes for Singlet Oxygen Emission with Induced Chirality
Figliola, Carlotta; Chériaux, Camille; Oppé, Nicolas; Estaque, Lilian; Retailleau, Pascal; Vanthuyne, Nicolas; Pieters, Gregory; Jacquemin, Denis; Ulrich, Gilles; Chemical Communications  (2026) –; doi:10.1039/D5CC06879G

data_7135323
_publ_section_title
;
 Design of Heavy-Atom Free Dipyridomethene Boron Complexes for Singlet
 Oxygen Emission with Induced Chirality
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC06879G
_journal_year                    2026
_chemical_formula_moiety         'C19 H14 B F2 N3 O'
_chemical_formula_sum            'C19 H14 B F2 N3 O'
_chemical_formula_weight         349.164
_chemical_name_common
6,6-difluoro-4-(2-methoxyphenyl)-6H-6\l4,7\l4-dipyrido[1,2-c:2',1'-f][1,3,2]diazaborinine-12-carbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     other
_audit_creation_date             2022-09-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-17 deposited with the CCDC.	2025-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.445(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1316(4)
_cell_length_b                   18.2559(6)
_cell_length_c                   8.0791(3)
_cell_measurement_reflns_used    13114
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.7470
_cell_measurement_theta_min      3.0850
_cell_volume                     1619.56(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9992
_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    -27.00  94.00   0.50    5.00    --    4.10  38.00-120.00  242
  2  \w    -27.00  94.00   0.50    5.00    --    4.10  38.00 150.00  242
  3  \w    -25.00  94.00   0.50    5.00    --    4.10  57.00 -60.00  238
  4  \w    -25.00  82.00   0.50    5.00    --    4.10  57.00-180.00  214
  5  \w    -25.00  91.00   0.50    5.00    --    4.10  57.00 -90.00  232
  6  \w    -34.00  72.00   0.50    5.00    --   -4.40  57.00-150.00  212
  7  \w     10.00  78.00   0.50    5.00    --   -4.40  57.00  60.00  136
  8  \w    -34.00  -1.00   0.50    5.00    --   -4.40  57.00  60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131409000
_diffrn_orient_matrix_UB_12      -0.0330911000
_diffrn_orient_matrix_UB_13      -0.0394259000
_diffrn_orient_matrix_UB_21      0.0084009000
_diffrn_orient_matrix_UB_22      -0.0180900000
_diffrn_orient_matrix_UB_23      0.0787935000
_diffrn_orient_matrix_UB_31      -0.0626648000
_diffrn_orient_matrix_UB_32      -0.0093339000
_diffrn_orient_matrix_UB_33      -0.0127368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.9992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            49352
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9992
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.1409
_refine_diff_density_min         -0.1339
_refine_diff_density_rms         0.0275
_refine_ls_d_res_high            0.7601
_refine_ls_d_res_low             7.3039
_refine_ls_goodness_of_fit_ref   1.0778
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     361
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0778
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0196
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0102P)^2^+0.0744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0382
_refine_ls_wR_factor_ref         0.0411
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                3147
_reflns_number_total             3868
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc06879g2.cif
_cod_data_source_block           cmpd_1a_CBF-68-QM
_cod_database_code               7135323
_chemical_oxdiff_formula         'C14 H12  B F2  N3 O1 '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
;
_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 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.762