Synthesis of phenanthrylboroles and formal nitrene insertion to access azaborapyrenes.
Zacharias, Harie; Begum, Ayesha; Han, Jianhua; Bartholome, Tyler A.; Marder, Todd B.; Martin, Caleb D.; Chemical communications (Cambridge, England) 60 (2024) 8740–8743; doi:10.1039/d4cc02863e

data_7133356
_publ_section_title
;
 Synthesis of phenanthrylboroles and formal nitrene insertion to access
 azaborapyrenes.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8740
_journal_page_last               8743
_journal_paper_doi               10.1039/d4cc02863e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         C21H15BClN
_chemical_formula_sum            'C21 H15 B Cl N'
_chemical_formula_weight         327.60
_chemical_name_systematic        3Ph
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-24 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4556(3)
_cell_length_b                   16.6414(13)
_cell_length_c                   17.5759(13)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.45
_cell_volume                     1595.70(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43931
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.728
_diffrn_reflns_theta_min         2.621
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method
'Vapor diffusion of Chloroform into Toluene'
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0409P)^2^+0.5194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3222
_reflns_number_total             3377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02863e2.cif
_cod_data_source_block           3Ph
_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.

data item '_atom_sites_solution_primary' value 'DIRECT METHODS' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133355--7133356.cif.
;
_cod_database_code               7133356
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.911
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              33422
_shelx_hkl_checksum              56843