##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4.3
_journal_data_validation_number     ?
_journal_date_recd_electronic     2017-10-28
_journal_date_accepted     2017-11-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue     12
_journal_page_first     1917
_journal_page_last     1920
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017016553
_journal_coeditor_code     RZ5224
_publ_contact_author_name
;
Ledesma, Gabriela
;
_publ_contact_author_address
;
IQUIR (Instituto de Química Rosario), Consejo Nacional de Investigaciones
 Cientificas y Tecnicas (CONICET), Facultad de Ciencias Bioquimicas y
 Farmaceuticas, Universidad Nacional de Rosario, Suipacha 531, (S2002LRK),
 Rosario, Argentina
;
_publ_contact_author_email     'ledesma@iquir-conicet.gov.ar'
_publ_contact_author_fax
;
54 341 437 0477
;
_publ_contact_author_phone
;
54 341 435 0214
;
_publ_section_title
;\
Crystal structure of
cis-1-phenyl-8-(pyridin-2-ylmethyl)dibenzo[1,2-c:2,1-\
h]-2,14-dioxa-8-aza-1-borabicyclo[4.4.0]deca-3,8-diene
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ledesma, Gabriela' .
;
IQUIR (Instituto de Química Rosario)
Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET),
Facultad de Ciencias Bioquímicas y Farmacéuticas,
Universidad Nacional de Rosario,
Suipacha 531, (S2002LRK),
Rosario,
Argentina
;
    'Signorella, Sandra' .
;
IQUIR (Instituto de Química Rosario)
Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET),
Facultad de Ciencias Bioquímicas y Farmacéuticas,
Universidad Nacional de Rosario,
Suipacha 531, (S2002LRK),
Rosario,
Argentina
;
    'Back, Davi' .
;
Laboratório de Materiais Inorgânicos
Department of Chemistry
Federal University of Santa Maria, UFSM
97115-900 Santa Maria, RS,
Brazil
;
    'Schulz Lang, Ernesto' .
;
Laboratório de Materiais Inorganicos
Department of Chemistry
Federal University of Santa Maria, UFSM
97115-900 Santa Maria, RS,
Brazil
;
_publ_section_synopsis
;
The present work describes the synthesis and crystal structure of the new
B-phenyloxazaborocine, C₂₆H₂₃BN₂O₂. The title compound adopts a
zwitterionic form with a significant intramolecular N\\rightarrowB dative bond
and intermolecular C---H...O interactions connecting molecules parallel to the
b axis.
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;\
cis-1-Phenyl-8-(pyridin-2-ylmethyl)dibenzo[1,2-c:\
2,1-h]-2,14-dioxa-8-aza-1-borabicyclo[4.4.0]deca-3,8-diene
;
_chemical_formula_moiety     'C26 H23 B N2 O2'
_chemical_formula_sum     'C26 H23 B N2 O2'
_chemical_formula_weight     406.27
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.8803(7)
_cell_length_b     10.0871(8)
_cell_length_c     11.7586(10)
_cell_angle_alpha     97.298(2)
_cell_angle_beta     98.464(2)
_cell_angle_gamma     98.234(2)
_cell_volume     1019.21(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5951
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     28.18
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.324
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     428
_exptl_absorpt_coefficient_mu     0.083
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(XPREP and SADABS; Bruker, 2008)
;
_exptl_absorpt_correction_T_min     0.7804
_exptl_absorpt_correction_T_max     0.8748
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     8344
_diffrn_reflns_av_R_equivalents     0.0876
_diffrn_reflns_theta_min     2.351
_diffrn_reflns_theta_max     25.991
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4004
_reflns_number_gt     2161
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1478
_refine_ls_R_factor_gt     0.0591
_refine_ls_wR_factor_ref     0.1153
_refine_ls_goodness_of_fit_ref     0.924
_refine_ls_restrained_S_all     0.924
_refine_ls_number_reflns     4004
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0336P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.254
_refine_diff_density_min     -0.308
_refine_ls_extinction_method     none
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O2 0.33571(19) 0.80339(16) 0.66654(14) 0.0162(4) Uani d 1 . .
    C C7 0.2240(3) 0.5768(2) 0.7698(2) 0.0154(6) Uani d 1 . .
    H H7A 0.186984 0.481569 0.777707 0.018 Uiso calc 1 . .
    H H7B 0.15142 0.602455 0.707238 0.018 Uiso calc 1 . .
    O O1 0.45343(19) 0.81457(16) 0.86313(14) 0.0155(4) Uani d 1 . .
    N N1 0.3811(2) 0.58730(19) 0.73635(17) 0.0142(5) Uani d 1 . .
    N N2 0.3294(3) 0.3306(2) 0.87553(18) 0.0228(6) Uani d 1 . .
    C C1 0.3311(3) 0.7832(2) 0.9193(2) 0.0141(6) Uani d 1 . .
    C C15 0.6210(3) 0.7798(2) 0.7133(2) 0.0145(6) Uani d 1 . .
    C C6 0.2247(3) 0.6666(2) 0.8822(2) 0.0143(6) Uani d 1 . .
    C C8 0.2760(3) 0.7354(2) 0.5582(2) 0.0149(6) Uani d 1 . .
    C C22 0.4325(3) 0.3686(2) 0.8075(2) 0.0164(6) Uani d 1 . .
    C C20 0.6479(3) 0.8046(2) 0.6034(2) 0.0168(6) Uani d 1 . .
    H H20 0.562356 0.799166 0.543102 0.02 Uiso calc 1 . .
    C C14 0.3653(3) 0.5215(2) 0.6124(2) 0.0159(6) Uani d 1 . .
    H H14A 0.469245 0.515167 0.593371 0.019 Uiso calc 1 . .
    H H14B 0.307445 0.428216 0.603349 0.019 Uiso calc 1 . .
    C C13 0.2833(3) 0.5988(2) 0.5288(2) 0.0154(6) Uani d 1 . .
    C C2 0.3191(3) 0.8716(3) 1.0178(2) 0.0184(6) Uani d 1 . .
    H H2 0.391788 0.952737 1.042134 0.022 Uiso calc 1 . .
    C C19 0.7968(3) 0.8371(3) 0.5794(2) 0.0218(7) Uani d 1 . .
    H H19 0.811445 0.851654 0.503233 0.026 Uiso calc 1 . .
    C C3 0.2016(3) 0.8410(3) 1.0797(2) 0.0209(7) Uani d 1 . .
    H H3 0.192493 0.901899 1.145982 0.025 Uiso calc 1 . .
    C C26 0.4860(3) 0.2759(2) 0.7329(2) 0.0183(6) Uani d 1 . .
    H H26 0.56079 0.305733 0.687579 0.022 Uiso calc 1 . .
    C C5 0.1087(3) 0.6353(3) 0.9472(2) 0.0195(6) Uani d 1 . .
    H H5 0.036794 0.553633 0.923746 0.023 Uiso calc 1 . .
    C C9 0.2030(3) 0.8050(3) 0.4773(2) 0.0190(7) Uani d 1 . .
    H H9 0.198548 0.898346 0.497886 0.023 Uiso calc 1 . .
    C C16 0.7521(3) 0.7913(2) 0.7980(2) 0.0197(7) Uani d 1 . .
    H H16 0.738836 0.77471 0.873908 0.024 Uiso calc 1 . .
    C C12 0.2147(3) 0.5337(3) 0.4180(2) 0.0183(6) Uani d 1 . .
    H H12 0.216587 0.439785 0.397566 0.022 Uiso calc 1 . .
    C C4 0.0970(3) 0.7221(3) 1.0458(2) 0.0226(7) Uani d 1 . .
    H H4 0.017669 0.699995 1.089651 0.027 Uiso calc 1 . .
    C C25 0.4296(3) 0.1387(3) 0.7247(2) 0.0222(7) Uani d 1 . .
    H H25 0.464256 0.073442 0.673508 0.027 Uiso calc 1 . .
    C C17 0.9002(3) 0.8257(3) 0.7761(2) 0.0217(7) Uani d 1 . .
    H H17 0.986288 0.834068 0.836496 0.026 Uiso calc 1 . .
    C C10 0.1376(3) 0.7395(3) 0.3682(2) 0.0223(7) Uani d 1 . .
    H H10 0.087663 0.787534 0.313513 0.027 Uiso calc 1 . .
    C C21 0.4862(3) 0.5193(2) 0.8156(2) 0.0168(6) Uani d 1 . .
    H H21A 0.591196 0.534146 0.795601 0.02 Uiso calc 1 . .
    H H21B 0.492924 0.562668 0.896988 0.02 Uiso calc 1 . .
    C C24 0.3225(3) 0.0994(3) 0.7923(2) 0.0204(7) Uani d 1 . .
    H H24 0.2805 0.006461 0.788101 0.024 Uiso calc 1 . .
    C C11 0.1438(3) 0.6029(3) 0.3371(2) 0.0224(7) Uani d 1 . .
    H H11 0.099895 0.557761 0.260997 0.027 Uiso calc 1 . .
    C C18 0.9221(3) 0.8480(2) 0.6656(2) 0.0226(7) Uani d 1 . .
    H H18 1.023545 0.870859 0.649451 0.027 Uiso calc 1 . .
    C C23 0.2776(3) 0.1973(3) 0.8658(2) 0.0239(7) Uani d 1 . .
    H H23 0.204908 0.168795 0.913098 0.029 Uiso calc 1 . .
    B B1 0.4511(3) 0.7520(3) 0.7450(3) 0.0153(7) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O2 C8 . 1.360(3) ?
    O2 B1 . 1.471(3) ?
    C7 N1 . 1.497(3) ?
    C7 C6 . 1.504(3) ?
    C7 H7A . 0.99 ?
    C7 H7B . 0.99 ?
    O1 C1 . 1.372(3) ?
    O1 B1 . 1.446(3) ?
    N1 C14 . 1.501(3) ?
    N1 C21 . 1.517(3) ?
    N1 B1 . 1.674(4) ?
    N2 C23 . 1.343(3) ?
    N2 C22 . 1.348(3) ?
    C1 C6 . 1.378(3) ?
    C1 C2 . 1.396(3) ?
    C15 C20 . 1.396(3) ?
    C15 C16 . 1.396(3) ?
    C15 B1 . 1.602(4) ?
    C6 C5 . 1.395(3) ?
    C8 C13 . 1.391(3) ?
    C8 C9 . 1.391(3) ?
    C22 C26 . 1.383(3) ?
    C22 C21 . 1.513(3) ?
    C20 C19 . 1.394(4) ?
    C20 H20 . 0.95 ?
    C14 C13 . 1.501(3) ?
    C14 H14A . 0.99 ?
    C14 H14B . 0.99 ?
    C13 C12 . 1.391(3) ?
    C2 C3 . 1.380(3) ?
    C2 H2 . 0.95 ?
    C19 C18 . 1.372(4) ?
    C19 H19 . 0.95 ?
    C3 C4 . 1.382(4) ?
    C3 H3 . 0.95 ?
    C26 C25 . 1.389(4) ?
    C26 H26 . 0.95 ?
    C5 C4 . 1.387(3) ?
    C5 H5 . 0.95 ?
    C9 C10 . 1.370(4) ?
    C9 H9 . 0.95 ?
    C16 C17 . 1.381(4) ?
    C16 H16 . 0.95 ?
    C12 C11 . 1.381(3) ?
    C12 H12 . 0.95 ?
    C4 H4 . 0.95 ?
    C25 C24 . 1.374(3) ?
    C25 H25 . 0.95 ?
    C17 C18 . 1.383(3) ?
    C17 H17 . 0.95 ?
    C10 C11 . 1.391(4) ?
    C10 H10 . 0.95 ?
    C21 H21A . 0.99 ?
    C21 H21B . 0.99 ?
    C24 C23 . 1.371(3) ?
    C24 H24 . 0.95 ?
    C11 H11 . 0.95 ?
    C18 H18 . 0.95 ?
    C23 H23 . 0.95 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C8 O2 B1 . . 121.39(18) ?
    N1 C7 C6 . . 111.9(2) ?
    N1 C7 H7A . . 109.2 ?
    C6 C7 H7A . . 109.2 ?
    N1 C7 H7B . . 109.2 ?
    C6 C7 H7B . . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    C1 O1 B1 . . 120.8(2) ?
    C7 N1 C14 . . 108.67(19) ?
    C7 N1 C21 . . 110.68(18) ?
    C14 N1 C21 . . 110.23(16) ?
    C7 N1 B1 . . 107.64(16) ?
    C14 N1 B1 . . 108.46(18) ?
    C21 N1 B1 . . 111.07(19) ?
    C23 N2 C22 . . 116.7(2) ?
    O1 C1 C6 . . 121.5(2) ?
    O1 C1 C2 . . 118.0(2) ?
    C6 C1 C2 . . 120.5(2) ?
    C20 C15 C16 . . 115.9(2) ?
    C20 C15 B1 . . 122.7(2) ?
    C16 C15 B1 . . 121.2(2) ?
    C1 C6 C5 . . 119.0(2) ?
    C1 C6 C7 . . 121.8(2) ?
    C5 C6 C7 . . 119.1(2) ?
    O2 C8 C13 . . 121.4(2) ?
    O2 C8 C9 . . 118.4(2) ?
    C13 C8 C9 . . 120.3(2) ?
    N2 C22 C26 . . 122.3(2) ?
    N2 C22 C21 . . 116.5(2) ?
    C26 C22 C21 . . 121.2(2) ?
    C19 C20 C15 . . 121.9(3) ?
    C19 C20 H20 . . 119 ?
    C15 C20 H20 . . 119 ?
    C13 C14 N1 . . 112.13(17) ?
    C13 C14 H14A . . 109.2 ?
    N1 C14 H14A . . 109.2 ?
    C13 C14 H14B . . 109.2 ?
    N1 C14 H14B . . 109.2 ?
    H14A C14 H14B . . 107.9 ?
    C8 C13 C12 . . 118.6(2) ?
    C8 C13 C14 . . 121.8(2) ?
    C12 C13 C14 . . 119.6(2) ?
    C3 C2 C1 . . 119.9(3) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C18 C19 C20 . . 120.1(3) ?
    C18 C19 H19 . . 120 ?
    C20 C19 H19 . . 120 ?
    C2 C3 C4 . . 120.3(2) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C22 C26 C25 . . 119.4(2) ?
    C22 C26 H26 . . 120.3 ?
    C25 C26 H26 . . 120.3 ?
    C4 C5 C6 . . 120.8(3) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C10 C9 C8 . . 120.3(2) ?
    C10 C9 H9 . . 119.9 ?
    C8 C9 H9 . . 119.9 ?
    C17 C16 C15 . . 122.9(2) ?
    C17 C16 H16 . . 118.6 ?
    C15 C16 H16 . . 118.6 ?
    C11 C12 C13 . . 121.2(2) ?
    C11 C12 H12 . . 119.4 ?
    C13 C12 H12 . . 119.4 ?
    C3 C4 C5 . . 119.5(3) ?
    C3 C4 H4 . . 120.3 ?
    C5 C4 H4 . . 120.3 ?
    C24 C25 C26 . . 118.6(2) ?
    C24 C25 H25 . . 120.7 ?
    C26 C25 H25 . . 120.7 ?
    C16 C17 C18 . . 119.5(3) ?
    C16 C17 H17 . . 120.3 ?
    C18 C17 H17 . . 120.3 ?
    C9 C10 C11 . . 120.4(2) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C22 C21 N1 . . 113.5(2) ?
    C22 C21 H21A . . 108.9 ?
    N1 C21 H21A . . 108.9 ?
    C22 C21 H21B . . 108.9 ?
    N1 C21 H21B . . 108.9 ?
    H21A C21 H21B . . 107.7 ?
    C23 C24 C25 . . 118.5(3) ?
    C23 C24 H24 . . 120.8 ?
    C25 C24 H24 . . 120.8 ?
    C12 C11 C10 . . 119.2(3) ?
    C12 C11 H11 . . 120.4 ?
    C10 C11 H11 . . 120.4 ?
    C19 C18 C17 . . 119.7(3) ?
    C19 C18 H18 . . 120.1 ?
    C17 C18 H18 . . 120.1 ?
    N2 C23 C24 . . 124.5(3) ?
    N2 C23 H23 . . 117.8 ?
    C24 C23 H23 . . 117.8 ?
    O1 B1 O2 . . 108.95(17) ?
    O1 B1 C15 . . 109.5(2) ?
    O2 B1 C15 . . 113.0(2) ?
    O1 B1 N1 . . 107.1(2) ?
    O2 B1 N1 . . 104.5(2) ?
    C15 B1 N1 . . 113.46(17) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C2 H2 O1 2_677 0.95 2.57 3.503(3) 167.5
    C24 H24 O2 1_545 0.95 2.50 3.185(3) 129.4
