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_1575909
_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         '0.5(C H2 Cl2), C50 H42 B2 N2 O4'
_chemical_formula_sum            'C50.5 H43 B2 Cl N2 O4'
_chemical_formula_weight         798.94
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-09
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6496)
;
_audit_update_record
;
2025-07-15 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                97.5230(10)
_cell_angle_beta                 100.3440(10)
_cell_angle_gamma                113.7920(10)
_cell_formula_units_Z            4
_cell_length_a                   14.1640(3)
_cell_length_b                   17.1362(4)
_cell_length_c                   18.8082(4)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.37
_cell_measurement_theta_min      3.34
_cell_volume                     4002.98(16)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            105182
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.531
_diffrn_reflns_theta_min         2.893
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0980 before and 0.0582 after correction.
The Ratio of minimum to maximum transmission is 0.8798.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1676
_refine_diff_density_max         1.335
_refine_diff_density_min         -1.003
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1177
_refine_ls_number_reflns         16113
_refine_ls_number_restraints     225
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0847P)^2^+2.5015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13543
_reflns_number_total             16113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05407a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1575908--1575909.cif.'
_cod_original_formula_sum        'C50.50 H43 B2 Cl N2 O4'
_cod_database_code               1575909
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
C7 \\sim C10 \\sim C8 \\sim C9 \\sim C10A \\sim C8A \\sim C9A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C27 \\sim C28 \\sim C24 \\sim C25 \\sim C28A \\sim C25A \\sim C24A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C17 \\sim C19 \\sim C18 \\sim C20 \\sim C20A \\sim C18A \\sim C19A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
2. Same fragment restrains
{C7, C10A, C8A, C9A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C7, C10, C8, C9}
{C27, C28A, C25A, C24A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C27, C28, C24, C25}
{C17, C20A, C18A} sigma for 1-2: 0.01, 1-3: 0.01
as in
{C17, C19, C18}
3. Others
 Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=
 Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=1-FVAR(1)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(1)
 Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=
 Sof(H25F)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(2)
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(2)
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=
 Sof(H18F)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(3)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C032(H03A,H03B)
4.b Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00W(H00W), C011(H011), C016(H016), C018(H018), C01B(H01B),
 C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01J(H01J),
 C01L(H01L), C12(H12), C01N(H01N), C6(H6), C01Q(H01Q), C01R(H01R), C01S(H01S),
 C01U(H01U), C01W(H01W), C22(H22), C5(H5), C020(H020), C021(H021), C023(H023),
 C024(H024), C025(H025), C026(H026), C027(H027), C028(H028), C23(H23),
 C02A(H02A), C13(H13), C02D(H02D), C02E(H02E), C02G(H02G), C02H(H02H), C16(H16),
  C02K(H02K), C02L(H02L), C02M(H02M), C02N(H02N), C02P(H02P), C15(H15),
 C02T(H02T), C02U(H02U), C02W(H02W)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C28(H28A,H28B,H28C),
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C19(H19A,H19B,H19C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C), C10A(H10D,H10E,H10F), C8A(H8AA,H8AB,H8AC),
 C9A(H9AA,H9AB,H9AC), C28A(H28D,H28E,H28F), C25A(H25D,H25E,H25F), C24A(H24D,
 H24E,H24F), C20A(H20D,H20E,H20F), C18A(H18D,H18E,H18F), C19A(H19D,H19E,H19F),
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              89827
_olex2_submission_special_instructions 'No special instructions were received'