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_7135324
_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         'C22 H13 B F N3 O'
_chemical_formula_sum            'C22 H13 B F N3 O'
_chemical_formula_weight         365.191
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2025-07-18
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-07-18 deposited with the CCDC.	2025-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                95.850(7)
_cell_angle_beta                 95.816(7)
_cell_angle_gamma                103.652(7)
_cell_formula_units_Z            2
_cell_length_a                   7.5432(4)
_cell_length_b                   8.0975(5)
_cell_length_c                   14.2914(10)
_cell_measurement_reflns_used    4139
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.7
_cell_measurement_theta_min      3.1
_cell_volume                     836.72(10)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac6-016 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Rapid 2 large curved IP'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.9681
_diffrn_measured_fraction_theta_max 0.9668
_diffrn_measurement_device
;
Crystal Goniometer chi-partial 
;
_diffrn_measurement_device_type
;
Rigaku Rapid2
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  'Confocal CMF optics'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.9681
_diffrn_reflns_Laue_measured_fraction_max 0.9668
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10478
_diffrn_reflns_point_group_measured_fraction_full 0.9681
_diffrn_reflns_point_group_measured_fraction_max 0.9668
_diffrn_reflns_theta_full        67.6868
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         5.67
_diffrn_source                   'Rotating Anode mm007HF'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Abscor (Higashi-Rigaku, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: octane/dichloromethane'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.2875
_refine_diff_density_min         -0.2887
_refine_diff_density_rms         0.0741
_refine_ls_d_res_high            0.8303
_refine_ls_d_res_low             7.8018
_refine_ls_goodness_of_fit_ref   0.9641
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    1
_refine_ls_number_parameters     364
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9641
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.0203P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1896
_reflns_number_total             2981
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc06879g2.cif
_cod_data_source_block           cmpd_1d_CFB-85
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7135324
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_olex2_refine_details
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing
 cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         B3LYP
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   SOLVATION:      CH2CL2
   DATE:           2025-07-18_09-46-07
;
_olex2_submission_special_instructions 'No special instructions were received'