A zwitterion produced by a strong intramolecular N→ B interaction in 1-hydroxy-2-(pyridin-2-ylcarbonyl)benzo[<i>d</i>][1,2,3]diazaborinine
Sarina, Evan A.; Olmstead, Marilyn M.; Kanichar, Divya; Groziak, Michael P.; Acta Crystallographica Section C 71 (2015) –; doi:10.1107/S2053229615021841

data_2020300
_publ_section_title
;
 A zwitterion produced by a strong intramolecular N\\rightarrow B
 interaction in
 1-hydroxy-2-(pyridin-2-ylcarbonyl)benzo[<i>d</i>][1,2,3]diazaborinine
;
_journal_coeditor_code           YP3108
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615021841
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H10 B N3 O2'
_chemical_formula_moiety         'C13 H10 B N3 O2'
_chemical_formula_sum            'C13 H10 B N3 O2'
_chemical_formula_weight         251.05
_chemical_name_systematic
1-Hydroxy-11-oxo-9,10,17\l^5^-triaza-1\l^4^-boratetracyclo[8.7.0.0^2,7^.0^12,17^]heptadeca-3,5,7,12,14,16-hexaen-17-ylium-1-uide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 117.8900(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6613(9)
_cell_length_b                   8.0054(6)
_cell_length_c                   12.8345(9)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      33.34
_cell_measurement_theta_min      3.10
_cell_volume                     1149.79(14)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
Apex2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL, XP (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL-2014/7 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015)
;
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19673
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.571
_diffrn_reflns_theta_min         3.098
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.468
_exptl_crystal_size_min          0.406
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0626P)^2^+0.3289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                3852
_reflns_number_total             4160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yp3108sup1.cif
_cod_data_source_block           I
_cod_database_code               2020300
_cod_database_fobs_code          2020300
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.961
_shelx_hkl_checksum              50962
_shelx_res_checksum              71106