Metal-free alkyne annulation enabling π-extension of boron-doped polycyclic aromatic hydrocarbons.
Anitha, Mandala; Chin, To-Jen; Liu, Guan-Cheng; Hsieh, Chi-Tien; Wang, Kuan-Hua; Li, Shu-Li; Cheng, Mu-Jeng; Farrell, Jeffrey M.; Chemical science 15 (2024) 16210–16215; doi:10.1039/d4sc03781b

data_1573013
_publ_section_title
;
 Metal-free alkyne annulation enabling &#x3c0;-extension of boron-doped
 polycyclic aromatic hydrocarbons.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16210
_journal_page_last               16215
_journal_paper_doi               10.1039/d4sc03781b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C48 H38 B2'
_chemical_formula_weight         636.40
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-03-20 deposited with the CCDC.	2024-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.113(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.8935(12)
_cell_length_b                   7.5081(4)
_cell_length_c                   11.7916(7)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.94
_cell_measurement_theta_min      4.45
_cell_volume                     1760.02(18)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27436
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.178
_diffrn_reflns_theta_min         2.222
_diffrn_source                   'I-mu-S microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0658P)^2^+0.6866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3139
_reflns_number_total             3433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03781b2.cif
_cod_data_source_block           ic22339
_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/current/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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1573013
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              29289
_shelx_hkl_checksum              16599