Amino-acid derived benzazaboroles: structure and function of a new chemotype.
O'Brien, Cyril J; Ospanow, Elisa; Reznikov, Karin; Soleimani, Ebrahim; Lanteigne, Martin; Tanner, Carol A.; Haltli, Bradley A.; Dmitrienko, Gary I.; Robertson, Katherine N.; Jakeman, David L.; Organic & biomolecular chemistry 23 (2025) 7786–7792; doi:10.1039/d5ob00948k

data_7160683
_publ_section_title
;
 Amino-acid derived benzazaboroles: structure and function of a new
 chemotype.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7786
_journal_page_last               7792
_journal_paper_doi               10.1039/d5ob00948k
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety
;          
C15 H19 B N2 O5 S, H2 O, 0.167(O)
;
_chemical_formula_sum            'C15 H21 B N2 O6.17 S'
_chemical_formula_weight         370.87
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-05-18 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   21.0230(12)
_cell_length_b                   21.0230(12)
_cell_length_c                   6.7207(6)
_cell_measurement_reflns_used    9296
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.2417
_cell_measurement_theta_min      4.8580
_cell_volume                     2572.4(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            62210
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.446
_diffrn_reflns_theta_min         4.206
_diffrn_source_current           1.1
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.005
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, 
G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       needle
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.087(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3500
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0231
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.4622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0643
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3489
_reflns_number_total             3500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00948k2.cif
_cod_data_source_block           compound7_DJ002
_cod_depositor_comments          'Adding full bibliography for 7160683.cif.'
_cod_original_cell_volume        2572.4(4)
_cod_database_code               7160683
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.493
_shelx_estimated_absorpt_t_max   0.834
_diffrn_source_source            'microfocus sealed tube'
_shelx_res_checksum              67917