##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;\
10-{4-[(2-Hydroxybenzylidene)amino]phenyl}-5,5-difluoro-1,3,7,9-tetramethyl-\
5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-\
uide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H24 B F2 N3 O'
_chemical_formula_sum     'C26 H24 B F2 N3 O'
_chemical_formula_iupac     'C26 H24 B F2 N3 O'
_chemical_formula_weight     443.29
_chemical_melting_point     ?
_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     8.8920(15)
_cell_length_b     10.7480(17)
_cell_length_c     12.9230(18)
_cell_angle_alpha     110.258(9)
_cell_angle_beta     90.952(6)
_cell_angle_gamma     108.408(7)
_cell_volume     1088.3(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3734
_cell_measurement_theta_min     1.70
_cell_measurement_theta_max     27.90
_cell_measurement_temperature     113(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.353
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     464
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.9776
_exptl_absorpt_correction_T_max     0.9832
_exptl_special_details     ?
_diffrn_ambient_temperature     113(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     multilayer
_diffrn_measurement_device_type     'Rigaku Saturn724 CCD-detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     14.222
_diffrn_reflns_number     12167
_diffrn_reflns_av_R_equivalents     0.0535
_diffrn_reflns_av_sigmaI/netI     0.1060
_diffrn_reflns_theta_min     1.70
_diffrn_reflns_theta_max     28.01
_diffrn_reflns_theta_full     28.01
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_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 >
σ(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     5171
_reflns_number_gt     2822
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1000
_refine_ls_R_factor_gt     0.0709
_refine_ls_wR_factor_gt     0.2093
_refine_ls_wR_factor_ref     0.2173
_refine_ls_goodness_of_fit_ref     1.092
_refine_ls_restrained_S_all     1.092
_refine_ls_number_reflns     5171
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1035P)²+0.5082P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.767
_refine_diff_density_min     -0.435
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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' 0.0000 0.0000
                         '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 0.0060
                         '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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrystalClear-SM Expert (Rigaku, 2009)'
_computing_cell_refinement     'CrystalClear-SM Expert (Rigaku, 2009)'
_computing_data_reduction     'CrystalClear-SM Expert (Rigaku, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'CrystalStructure (Rigaku, 2009)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    F F1 0.8363(2) 0.60168(18) 0.29484(15) 0.0237(4) Uani d . 1 1 . .
    F F2 0.7383(2) 0.73948(19) 0.23512(15) 0.0258(5) Uani d . 1 1 . .
    O O1 -0.5899(3) 0.0147(3) 0.1083(2) 0.0422(7) Uani d . 1 1 . .
    H H1 -0.4899 0.0534 0.1182 0.063 Uiso calc R 1 1 . .
    N N1 0.5942(3) 0.6362(3) 0.3580(2) 0.0185(6) Uani d . 1 1 . .
    N N2 0.5944(3) 0.4878(3) 0.1630(2) 0.0172(5) Uani d . 1 1 . .
    N N3 -0.2990(3) 0.1062(3) 0.2134(2) 0.0273(7) Uani d . 1 1 . .
    C C1 0.6416(4) 0.7349(3) 0.4619(3) 0.0216(7) Uani d . 1 1 . .
    C C2 0.5163(4) 0.7140(3) 0.5250(3) 0.0248(7) Uani d . 1 1 . .
    H H2 0.5190 0.7695 0.6008 0.030 Uiso calc R 1 1 . .
    C C3 0.3881(4) 0.5993(3) 0.4586(3) 0.0214(7) Uani d . 1 1 . .
    C C4 0.4365(4) 0.5496(3) 0.3526(2) 0.0177(6) Uani d . 1 1 . .
    C C5 0.3579(4) 0.4373(3) 0.2536(2) 0.0176(6) Uani d . 1 1 . .
    C C6 0.4352(4) 0.4064(3) 0.1602(2) 0.0178(6) Uani d . 1 1 . .
    C C7 0.3803(4) 0.3018(3) 0.0502(2) 0.0191(7) Uani d . 1 1 . .
    C C8 0.5079(4) 0.3232(3) -0.0097(3) 0.0224(7) Uani d . 1 1 . .
    H H8 0.5078 0.2698 -0.0856 0.027 Uiso calc R 1 1 . .
    C C9 0.6371(4) 0.4374(3) 0.0616(3) 0.0204(7) Uani d . 1 1 . .
    C C10 0.8032(4) 0.8467(3) 0.4960(3) 0.0290(8) Uani d . 1 1 . .
    H H10A 0.8851 0.8034 0.4958 0.043 Uiso calc R 1 1 . .
    H H10B 0.8089 0.9145 0.5710 0.043 Uiso calc R 1 1 . .
    H H10C 0.8218 0.8956 0.4434 0.043 Uiso calc R 1 1 . .
    C C11 0.2300(4) 0.5436(4) 0.4972(3) 0.0275(8) Uani d . 1 1 . .
    H H11A 0.2004 0.4414 0.4771 0.041 Uiso calc R 1 1 . .
    H H11B 0.1473 0.5634 0.4612 0.041 Uiso calc R 1 1 . .
    H H11C 0.2399 0.5897 0.5782 0.041 Uiso calc R 1 1 . .
    C C12 0.2217(4) 0.1875(3) 0.0032(3) 0.0261(8) Uani d . 1 1 . .
    H H12A 0.2071 0.1566 -0.0782 0.039 Uiso calc R 1 1 . .
    H H12B 0.1364 0.2234 0.0325 0.039 Uiso calc R 1 1 . .
    H H12C 0.2174 0.1075 0.0245 0.039 Uiso calc R 1 1 . .
    C C13 0.8007(4) 0.4954(4) 0.0331(3) 0.0260(7) Uani d . 1 1 . .
    H H13A 0.8350 0.5986 0.0611 0.039 Uiso calc R 1 1 . .
    H H13B 0.7977 0.4587 -0.0480 0.039 Uiso calc R 1 1 . .
    H H13C 0.8763 0.4667 0.0674 0.039 Uiso calc R 1 1 . .
    C C14 0.1879(4) 0.3498(3) 0.2468(2) 0.0186(7) Uani d . 1 1 . .
    C C15 0.0661(4) 0.3993(3) 0.2304(3) 0.0214(7) Uani d . 1 1 . .
    H H15 0.0923 0.4909 0.2278 0.026 Uiso calc R 1 1 . .
    C C16 -0.0932(4) 0.3161(3) 0.2177(3) 0.0230(7) Uani d . 1 1 . .
    H H16 -0.1758 0.3485 0.2025 0.028 Uiso calc R 1 1 . .
    C C17 -0.1317(4) 0.1848(3) 0.2273(3) 0.0211(7) Uani d . 1 1 . .
    C C18 -0.0107(4) 0.1359(3) 0.2457(3) 0.0240(7) Uani d . 1 1 . .
    H H18 -0.0368 0.0467 0.2527 0.029 Uiso calc R 1 1 . .
    C C19 0.1484(4) 0.2175(3) 0.2539(3) 0.0218(7) Uani d . 1 1 . .
    H H19 0.2308 0.1826 0.2645 0.026 Uiso calc R 1 1 . .
    C C20 -0.3510(4) 0.0379(3) 0.2744(3) 0.0273(8) Uani d . 1 1 . .
    H H20 -0.2780 0.0384 0.3292 0.033 Uiso calc R 1 1 . .
    C C21 -0.5211(4) -0.0427(3) 0.2635(3) 0.0269(8) Uani d . 1 1 . .
    C C22 -0.6322(4) -0.0491(3) 0.1813(3) 0.0294(8) Uani d . 1 1 . .
    C C23 -0.7950(4) -0.1246(4) 0.1738(3) 0.0355(9) Uani d . 1 1 . .
    H H23 -0.8707 -0.1302 0.1181 0.043 Uiso calc R 1 1 . .
    C C24 -0.8441(4) -0.1901(4) 0.2471(3) 0.0360(9) Uani d . 1 1 . .
    H H24 -0.9546 -0.2405 0.2426 0.043 Uiso calc R 1 1 . .
    C C25 -0.7343(5) -0.1839(4) 0.3286(3) 0.0375(9) Uani d . 1 1 . .
    H H25 -0.7702 -0.2302 0.3789 0.045 Uiso calc R 1 1 . .
    C C26 -0.5743(5) -0.1111(4) 0.3362(3) 0.0329(9) Uani d . 1 1 . .
    H H26 -0.4998 -0.1076 0.3916 0.039 Uiso calc R 1 1 . .
    B B1 0.6956(4) 0.6192(4) 0.2632(3) 0.0195(7) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    F1 B1 . 1.397(4) ?
    F2 B1 . 1.402(4) ?
    O1 C22 . 1.341(4) ?
    O1 H1 . 0.8400 ?
    N1 C1 . 1.348(4) ?
    N1 C4 . 1.402(4) ?
    N1 B1 . 1.528(4) ?
    N2 C9 . 1.345(4) ?
    N2 C6 . 1.401(4) ?
    N2 B1 . 1.541(4) ?
    N3 C20 . 1.254(4) ?
    N3 C17 . 1.432(4) ?
    C1 C2 . 1.398(4) ?
    C1 C10 . 1.492(4) ?
    C2 C3 . 1.379(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.416(4) ?
    C3 C11 . 1.510(4) ?
    C4 C5 . 1.397(4) ?
    C5 C6 . 1.390(4) ?
    C5 C14 . 1.489(4) ?
    C6 C7 . 1.431(4) ?
    C7 C8 . 1.388(4) ?
    C7 C12 . 1.493(4) ?
    C8 C9 . 1.402(4) ?
    C8 H8 . 0.9500 ?
    C9 C13 . 1.498(4) ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 C19 . 1.389(4) ?
    C14 C15 . 1.392(4) ?
    C15 C16 . 1.387(4) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.393(4) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.388(5) ?
    C18 C19 . 1.389(4) ?
    C18 H18 . 0.9500 ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.462(5) ?
    C20 H20 . 0.9500 ?
    C21 C26 . 1.386(5) ?
    C21 C22 . 1.407(5) ?
    C22 C23 . 1.401(5) ?
    C23 C24 . 1.366(5) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.394(6) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.373(5) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
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
    C22 O1 H1 . . 109.5 ?
    C1 N1 C4 . . 108.1(2) ?
    C1 N1 B1 . . 126.1(3) ?
    C4 N1 B1 . . 125.7(3) ?
    C9 N2 C6 . . 108.2(2) ?
    C9 N2 B1 . . 126.7(3) ?
    C6 N2 B1 . . 124.9(2) ?
    C20 N3 C17 . . 120.2(3) ?
    N1 C1 C2 . . 109.0(3) ?
    N1 C1 C10 . . 122.3(3) ?
    C2 C1 C10 . . 128.7(3) ?
    C3 C2 C1 . . 108.6(3) ?
    C3 C2 H2 . . 125.7 ?
    C1 C2 H2 . . 125.7 ?
    C2 C3 C4 . . 106.5(3) ?
    C2 C3 C11 . . 124.4(3) ?
    C4 C3 C11 . . 129.2(3) ?
    C5 C4 N1 . . 120.1(3) ?
    C5 C4 C3 . . 132.1(3) ?
    N1 C4 C3 . . 107.8(3) ?
    C6 C5 C4 . . 121.0(3) ?
    C6 C5 C14 . . 119.2(3) ?
    C4 C5 C14 . . 119.8(3) ?
    C5 C6 N2 . . 120.8(3) ?
    C5 C6 C7 . . 131.5(3) ?
    N2 C6 C7 . . 107.7(2) ?
    C8 C7 C6 . . 106.3(3) ?
    C8 C7 C12 . . 124.0(3) ?
    C6 C7 C12 . . 129.7(3) ?
    C7 C8 C9 . . 108.0(3) ?
    C7 C8 H8 . . 126.0 ?
    C9 C8 H8 . . 126.0 ?
    N2 C9 C8 . . 109.7(3) ?
    N2 C9 C13 . . 123.8(3) ?
    C8 C9 C13 . . 126.5(3) ?
    C1 C10 H10A . . 109.5 ?
    C1 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C1 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C3 C11 H11A . . 109.5 ?
    C3 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C3 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C7 C12 H12A . . 109.5 ?
    C7 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C7 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C9 C13 H13A . . 109.5 ?
    C9 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C9 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C19 C14 C15 . . 119.2(3) ?
    C19 C14 C5 . . 121.0(3) ?
    C15 C14 C5 . . 119.7(3) ?
    C16 C15 C14 . . 120.6(3) ?
    C16 C15 H15 . . 119.7 ?
    C14 C15 H15 . . 119.7 ?
    C15 C16 C17 . . 119.7(3) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    C18 C17 C16 . . 119.9(3) ?
    C18 C17 N3 . . 124.0(3) ?
    C16 C17 N3 . . 116.1(3) ?
    C17 C18 C19 . . 120.0(3) ?
    C17 C18 H18 . . 120.0 ?
    C19 C18 H18 . . 120.0 ?
    C14 C19 C18 . . 120.5(3) ?
    C14 C19 H19 . . 119.8 ?
    C18 C19 H19 . . 119.8 ?
    N3 C20 C21 . . 121.8(3) ?
    N3 C20 H20 . . 119.1 ?
    C21 C20 H20 . . 119.1 ?
    C26 C21 C22 . . 119.5(3) ?
    C26 C21 C20 . . 119.8(3) ?
    C22 C21 C20 . . 120.7(3) ?
    O1 C22 C23 . . 117.4(3) ?
    O1 C22 C21 . . 122.9(3) ?
    C23 C22 C21 . . 119.7(3) ?
    C24 C23 C22 . . 119.5(4) ?
    C24 C23 H23 . . 120.3 ?
    C22 C23 H23 . . 120.3 ?
    C23 C24 C25 . . 120.9(3) ?
    C23 C24 H24 . . 119.5 ?
    C25 C24 H24 . . 119.5 ?
    C26 C25 C24 . . 120.1(4) ?
    C26 C25 H25 . . 120.0 ?
    C24 C25 H25 . . 120.0 ?
    C25 C26 C21 . . 120.3(4) ?
    C25 C26 H26 . . 119.9 ?
    C21 C26 H26 . . 119.9 ?
    F1 B1 F2 . . 108.0(3) ?
    F1 B1 N1 . . 110.6(3) ?
    F2 B1 N1 . . 110.3(3) ?
    F1 B1 N2 . . 110.0(3) ?
    F2 B1 N2 . . 110.5(3) ?
    N1 B1 N2 . . 107.4(2) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C4 N1 C1 C2 . . . . -0.1(4) ?
    B1 N1 C1 C2 . . . . -178.8(3) ?
    C4 N1 C1 C10 . . . . -178.7(3) ?
    B1 N1 C1 C10 . . . . 2.6(5) ?
    N1 C1 C2 C3 . . . . 0.2(4) ?
    C10 C1 C2 C3 . . . . 178.7(3) ?
    C1 C2 C3 C4 . . . . -0.2(4) ?
    C1 C2 C3 C11 . . . . 180.0(3) ?
    C1 N1 C4 C5 . . . . -179.7(3) ?
    B1 N1 C4 C5 . . . . -1.0(5) ?
    C1 N1 C4 C3 . . . . -0.1(3) ?
    B1 N1 C4 C3 . . . . 178.6(3) ?
    C2 C3 C4 C5 . . . . 179.7(3) ?
    C11 C3 C4 C5 . . . . -0.4(6) ?
    C2 C3 C4 N1 . . . . 0.2(3) ?
    C11 C3 C4 N1 . . . . 180.0(3) ?
    N1 C4 C5 C6 . . . . 2.1(5) ?
    C3 C4 C5 C6 . . . . -177.4(3) ?
    N1 C4 C5 C14 . . . . -177.2(3) ?
    C3 C4 C5 C14 . . . . 3.3(5) ?
    C4 C5 C6 N2 . . . . -0.2(5) ?
    C14 C5 C6 N2 . . . . 179.0(3) ?
    C4 C5 C6 C7 . . . . -177.9(3) ?
    C14 C5 C6 C7 . . . . 1.4(5) ?
    C9 N2 C6 C5 . . . . -178.4(3) ?
    B1 N2 C6 C5 . . . . -2.9(4) ?
    C9 N2 C6 C7 . . . . -0.3(3) ?
    B1 N2 C6 C7 . . . . 175.3(3) ?
    C5 C6 C7 C8 . . . . 178.0(3) ?
    N2 C6 C7 C8 . . . . 0.1(3) ?
    C5 C6 C7 C12 . . . . -3.2(6) ?
    N2 C6 C7 C12 . . . . 179.0(3) ?
    C6 C7 C8 C9 . . . . 0.1(4) ?
    C12 C7 C8 C9 . . . . -178.9(3) ?
    C6 N2 C9 C8 . . . . 0.3(3) ?
    B1 N2 C9 C8 . . . . -175.1(3) ?
    C6 N2 C9 C13 . . . . -178.5(3) ?
    B1 N2 C9 C13 . . . . 6.1(5) ?
    C7 C8 C9 N2 . . . . -0.2(4) ?
    C7 C8 C9 C13 . . . . 178.5(3) ?
    C6 C5 C14 C19 . . . . 78.7(4) ?
    C4 C5 C14 C19 . . . . -102.0(4) ?
    C6 C5 C14 C15 . . . . -99.7(4) ?
    C4 C5 C14 C15 . . . . 79.6(4) ?
    C19 C14 C15 C16 . . . . -2.0(5) ?
    C5 C14 C15 C16 . . . . 176.4(3) ?
    C14 C15 C16 C17 . . . . 3.4(5) ?
    C15 C16 C17 C18 . . . . -2.1(5) ?
    C15 C16 C17 N3 . . . . 179.7(3) ?
    C20 N3 C17 C18 . . . . 41.8(4) ?
    C20 N3 C17 C16 . . . . -140.2(3) ?
    C16 C17 C18 C19 . . . . -0.4(5) ?
    N3 C17 C18 C19 . . . . 177.6(3) ?
    C15 C14 C19 C18 . . . . -0.6(5) ?
    C5 C14 C19 C18 . . . . -179.0(3) ?
    C17 C18 C19 C14 . . . . 1.8(5) ?
    C17 N3 C20 C21 . . . . 179.5(3) ?
    N3 C20 C21 C26 . . . . -176.9(3) ?
    N3 C20 C21 C22 . . . . 1.7(5) ?
    C26 C21 C22 O1 . . . . 179.8(3) ?
    C20 C21 C22 O1 . . . . 1.1(5) ?
    C26 C21 C22 C23 . . . . -0.1(5) ?
    C20 C21 C22 C23 . . . . -178.7(3) ?
    O1 C22 C23 C24 . . . . -179.3(3) ?
    C21 C22 C23 C24 . . . . 0.6(5) ?
    C22 C23 C24 C25 . . . . -0.6(5) ?
    C23 C24 C25 C26 . . . . 0.2(5) ?
    C24 C25 C26 C21 . . . . 0.4(5) ?
    C22 C21 C26 C25 . . . . -0.4(5) ?
    C20 C21 C26 C25 . . . . 178.3(3) ?
    C1 N1 B1 F1 . . . . 56.8(4) ?
    C4 N1 B1 F1 . . . . -121.7(3) ?
    C1 N1 B1 F2 . . . . -62.7(4) ?
    C4 N1 B1 F2 . . . . 118.8(3) ?
    C1 N1 B1 N2 . . . . 176.9(3) ?
    C4 N1 B1 N2 . . . . -1.6(4) ?
    C9 N2 B1 F1 . . . . -61.3(4) ?
    C6 N2 B1 F1 . . . . 124.0(3) ?
    C9 N2 B1 F2 . . . . 57.9(4) ?
    C6 N2 B1 F2 . . . . -116.8(3) ?
    C9 N2 B1 N1 . . . . 178.2(3) ?
    C6 N2 B1 N1 . . . . 3.5(4) ?
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
    _geom_hbond_publ_flag
    O1 H1 N3 1_555 0.84 1.89 2.618(4) 145 yes
    C16 H16 F1 1_455 0.95 2.53 3.150(5) 123 no
    C24 H24 F1 1_345 0.95 2.37 3.235(5) 151 no
data_global
_journal_date_recd_electronic     2013-05-22
_journal_date_accepted     2013-06-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      7
_journal_page_first     o1072
_journal_page_last     o1072
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813015523
_journal_coeditor_code     ZS2263
_publ_contact_author_name     'Zhensheng Li'
_publ_contact_author_address
;
      Key Laboraory of Photochemical Conversion and Optoelectronic Materials,
      Technical Institute of Physics and Chemistry
      Chinese Academy of Sciences
      Zhongguancun Donglu 29.
      100190 Beijing
      Peoples Republic of China
;
_publ_contact_author_email     'lizhensheng0723@hotmail.com'
_publ_contact_author_fax     '0086-010-62554670'
_publ_contact_author_phone     '0086-010-82543520'
_publ_section_title
;\
10-{4-[(2-Hydroxybenzylidene)amino]phenyl}-5,5-difluoro-1,3,7,9-tetramethyl-\
5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-\
uide
;
loop_
    _publ_author_name
    _publ_author_address
    'Li, Zhensheng'
;     Key Laboraory of Photochemical Conversion and Optoelectronic Materials,
      Technical Institute of Physics and Chemistry
      Chinese Academy of Sciences
      Zhongguancun Donglu 29
      100190 Beijing
      Peoples Republic of China
;
