O-B ← N perturbed polycyclic aromatic hydrocarbons: a straightforward synthesis strategy, and their photophysical and optical waveguide properties.
Zhao, Jinying; Yang, Qihang; Chen, Weibin; Xu, Nuo; Zhang, Qing; Zhao, Wenhao; Luo, Geng-Geng; Cui, Qiuhong; Huang, Jianhua; Chemical science 16 (2025) 20445–20456; doi:10.1039/d5sc05407a

data_1575908
_publ_section_title
;
 O-B &#x2190; N perturbed polycyclic aromatic hydrocarbons: a
 straightforward synthesis strategy, and their photophysical and optical
 waveguide properties.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              20445
_journal_page_last               20456
_journal_paper_doi               10.1039/d5sc05407a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C19 H23 B N O2'
_chemical_formula_sum            'C19 H23 B N O2'
_chemical_formula_weight         308.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2025-07-15 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.121(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.654(3)
_cell_length_b                   5.8046(9)
_cell_length_c                   31.238(6)
_cell_measurement_reflns_used    920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6310
_cell_measurement_theta_min      3.5450
_cell_volume                     3368.9(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.891
_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     44.00  70.00   1.00    6.00    --   16.96 178.00-150.00   26
  2  \w     -2.00  82.00   1.00    6.00    --   16.96  57.00  90.00   84
  3  \w    -21.00  84.00   1.00    6.00    --   16.96  19.00  30.00  105
  4  \w    -41.00  35.00   1.00    6.00    --   16.96 -57.00-150.00   76
  5  \w    -37.00   6.00   1.00    6.00    --  -17.43 -77.00 -90.00   43
  6  \w    -37.00  11.00   1.00    6.00    --  -17.43 -77.00 120.00   48
  7  \w     22.00  47.00   1.00    6.00    --  -17.43  57.00-180.00   25
  8  \w    -33.00  -8.00   1.00    6.00    --  -17.43 -77.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0372002000
_diffrn_orient_matrix_UB_12      0.0162523000
_diffrn_orient_matrix_UB_13      -0.0020190000
_diffrn_orient_matrix_UB_21      -0.0069440000
_diffrn_orient_matrix_UB_22      0.0037633000
_diffrn_orient_matrix_UB_23      -0.0226894000
_diffrn_orient_matrix_UB_31      -0.0047693000
_diffrn_orient_matrix_UB_32      0.1211533000
_diffrn_orient_matrix_UB_33      0.0009777000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.1118
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            14529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.108
_diffrn_reflns_theta_min         2.192
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             1320
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.2477
_refine_ls_R_factor_gt           0.1212
_refine_ls_shift/su_max          2.627
_refine_ls_shift/su_mean         0.100
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0856P)^2^+7.4673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2403
_refine_ls_wR_factor_ref         0.3022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1728
_reflns_number_total             4024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05407a2.cif
_cod_data_source_block           exp_14671_auto
_cod_depositor_comments
'Adding full bibliography for 1575908--1575909.cif.'
_cod_original_cell_volume        3369.0(10)
_cod_database_code               1575908
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00I(H00I,H00J), C00J(H00K,H00L), C00L(H00M,H00N), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00C(H00D), C00D(H00E), C00E(H00F), C00F(H00G)
2.d Idealised Me refined as rotating group:
 C00M(H00O,H00P,H00Q), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              66364
_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 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.724