##############################################################################
#                                                                            #
# 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
_database_code_depnum_ccdc_archive 'CCDC 1510400'
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2016-09-09
_journal_date_accepted     2016-10-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2016
_journal_volume     72
_journal_issue     11
_journal_page_first     1642
_journal_page_last     1644
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989016016704
_journal_coeditor_code     WM5325
_publ_contact_author_name     'Shao Ming Chi'
_publ_contact_author_address
;
College of Chemistry and Chemical Engineering,Yunnan Normal University, Kunming,
650500,
People's Republic of China
;
_publ_contact_author_email     'chishaoming@gmail.com'
_publ_contact_author_fax     '+0086-0871-65941088'
_publ_contact_author_phone     '+0086-15925122904'
_publ_section_title
;\
Crystal structure of
9-(dibromomethyl)-1,1-difluoro-3,7-dimethyl-1H-[1,3,5,2]\
oxadiazaborinino[3,4-a][1,8]naphthyridin-11-ium-1-uide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wang, Bang Zhong' .
;
College of Chemistry and Chemical Engineering, Yunnan Normal University,
Kunming,
650500,
People's Republic of China
;
    'Zhou, Jun Ping' .
;
College of Chemistry and Chemical Engineering, Yunnan Normal University,
Kunming,
650500,
People's Republic of China
;
    'Zhou, Yong' .
;
College of Chemistry and Chemical Engineering, Yunnan Normal University,
Kunming,
650500,
People's Republic of China
;
    'Luo, Jian Song' .
;
College of Chemistry and Chemical Engineering, Yunnan Normal University,
Kunming,
650500,
People's Republic of China
;
    'Chi, Shao Ming' .
;
College of Chemistry and Chemical Engineering, Yunnan Normal University,
Kunming,
650500,
People's Republic of China
;
_publ_section_synopsis
;
The molecule in the title compound, C₁₂H₁₀BBr₂F₂N₃O, exhibits point
group symmetry m.
;
_chemical_name_systematic
;\
9-(Dibromomethyl)-1,1-difluoro-3,7-dimethyl-1H-\
[1,3,5,2]oxadiazaborinino[3,4-a][1,8]naphthyridin-11-ium-1-uide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H10 B Br2 F2 N3 O'
_chemical_formula_sum     'C12 H10 B Br2 F2 N3 O'
_chemical_formula_iupac     'C12 H10 B Br2 F2 N3 O'
_chemical_formula_weight     420.86
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n m a'
_symmetry_space_group_name_Hall     '-P 2ac 2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z'
    '-x-1/2, y-1/2, z-1/2'
_cell_length_a     17.161(3)
_cell_length_b     7.2169(14)
_cell_length_c     11.678(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1446.3(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1765
_cell_measurement_theta_min     3.09
_cell_measurement_theta_max     26.00
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.933
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     816
_exptl_absorpt_coefficient_mu     5.627
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_absorpt_correction_T_min     0.2661
_exptl_absorpt_correction_T_max     0.3018
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13517
_diffrn_reflns_av_R_equivalents     0.1392
_diffrn_reflns_av_sigmaI/netI     0.0748
_diffrn_reflns_theta_min     3.32
_diffrn_reflns_theta_max     27.39
_diffrn_reflns_theta_full     27.39
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_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     1765
_reflns_number_gt     937
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1220
_refine_ls_R_factor_gt     0.0535
_refine_ls_wR_factor_gt     0.0985
_refine_ls_wR_factor_ref     0.1196
_refine_ls_goodness_of_fit_ref     0.954
_refine_ls_restrained_S_all     0.954
_refine_ls_number_reflns     1765
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0519P)²+0.0000P] 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     0.503
_refine_diff_density_min     -0.366
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0042(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'B' 'B' 0.0013 0.0007
                         '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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_reduction
;
CrystalStructure (Rigaku/MSC, 2006)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL-97 (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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.11449(3) 0.02946(8) 0.57510(5) 0.0624(3) Uani d . 1 1 . .
    B B1 0.1752(5) 0.2500 0.9765(7) 0.041(2) Uani d S 1 2 . .
    F F1 0.19639(16) 0.0919(4) 0.9205(3) 0.0585(8) Uani d . 1 1 . .
    N N1 0.1041(4) 0.2500 1.2022(6) 0.0524(16) Uani d S 1 2 . .
    N N2 0.0835(3) 0.2500 1.0005(5) 0.0349(13) Uani d S 1 2 . .
    N N3 0.0640(3) 0.2500 0.8049(5) 0.0385(14) Uani d S 1 2 . .
    O O1 0.2143(3) 0.2500 1.0882(5) 0.0558(14) Uani d S 1 2 . .
    C C1 0.2326(5) 0.2500 1.2869(8) 0.063(2) Uani d S 1 2 . .
    H H1A 0.2025 0.2500 1.3562 0.095 Uiso d SR 1 2 . .
    H H1B 0.2649 0.1414 1.2847 0.095 Uiso d R 1 1 . .
    C C2 0.1794(5) 0.2500 1.1872(7) 0.0450(19) Uani d S 1 2 . .
    C C3 0.0572(4) 0.2500 1.1095(7) 0.0408(18) Uani d S 1 2 . .
    C C4 -0.0249(5) 0.2500 1.1303(8) 0.055(2) Uani d S 1 2 . .
    H H4A -0.0433 0.2500 1.2079 0.065 Uiso d SR 1 2 . .
    C C5 -0.0760(4) 0.2500 1.0421(8) 0.049(2) Uani d S 1 2 . .
    H H5A -0.1309 0.2500 1.0579 0.059 Uiso d SR 1 2 . .
    C C6 -0.0513(4) 0.2500 0.9274(8) 0.0417(18) Uani d S 1 2 . .
    C C7 -0.1003(4) 0.2500 0.8304(7) 0.0435(19) Uani d S 1 2 . .
    C C8 -0.1880(4) 0.2500 0.8438(8) 0.060(2) Uani d S 1 2 . .
    H H8A -0.2125 0.2500 0.7698 0.089 Uiso d SR 1 2 . .
    H H8B -0.2036 0.1414 0.8854 0.089 Uiso d R 1 1 . .
    C C9 -0.0662(4) 0.2500 0.7256(7) 0.0463(19) Uani d S 1 2 . .
    H H9A -0.0981 0.2500 0.6580 0.056 Uiso d SR 1 2 . .
    C C10 0.0160(4) 0.2500 0.7152(7) 0.0424(18) Uani d S 1 2 . .
    C C11 0.0314(4) 0.2500 0.9079(6) 0.0349(17) Uani d S 1 2 . .
    C C12 0.0518(4) 0.2500 0.5979(7) 0.050(2) Uani d S 1 2 . .
    H H12A 0.0104 0.2500 0.5425 0.059 Uiso d SR 1 2 . .
_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
    Br1 C12 . 1.940(4) ?
    B1 F1 . 1.364(5) ?
    B1 F1 7_565 1.364(5) ?
    B1 O1 . 1.467(9) ?
    B1 N2 . 1.599(10) ?
    N1 C2 . 1.303(9) ?
    N1 C3 . 1.349(9) ?
    N2 C3 . 1.351(9) ?
    N2 C11 . 1.403(9) ?
    N3 C11 . 1.327(8) ?
    N3 C10 . 1.332(9) ?
    O1 C2 . 1.302(9) ?
    C1 C2 . 1.481(11) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C3 C4 . 1.431(10) ?
    C4 C5 . 1.353(11) ?
    C4 H4A . 0.9600 ?
    C5 C6 . 1.406(11) ?
    C5 H5A . 0.9600 ?
    C6 C7 . 1.410(11) ?
    C6 C11 . 1.437(9) ?
    C7 C9 . 1.357(10) ?
    C7 C8 . 1.514(9) ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C9 C10 . 1.416(9) ?
    C9 H9A . 0.9600 ?
    C10 C12 . 1.501(10) ?
    C12 Br1 7_565 1.940(4) ?
    C12 H12A . 0.9600 ?
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
    F1 B1 F1 . 7_565 113.6(7) ?
    F1 B1 O1 . . 107.7(4) ?
    F1 B1 O1 7_565 . 107.7(4) ?
    F1 B1 N2 . . 110.2(4) ?
    F1 B1 N2 7_565 . 110.2(4) ?
    O1 B1 N2 . . 107.1(6) ?
    C2 N1 C3 . . 118.9(7) ?
    C3 N2 C11 . . 120.9(6) ?
    C3 N2 B1 . . 119.6(6) ?
    C11 N2 B1 . . 119.5(6) ?
    C11 N3 C10 . . 116.9(6) ?
    C2 O1 B1 . . 125.4(6) ?
    C2 C1 H1A . . 109.3 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    N1 C2 O1 . . 125.2(7) ?
    N1 C2 C1 . . 120.4(8) ?
    O1 C2 C1 . . 114.4(7) ?
    N2 C3 N1 . . 123.9(7) ?
    N2 C3 C4 . . 119.2(7) ?
    N1 C3 C4 . . 116.9(7) ?
    C5 C4 C3 . . 120.7(8) ?
    C5 C4 H4A . . 120.4 ?
    C3 C4 H4A . . 119.0 ?
    C4 C5 C6 . . 122.0(7) ?
    C4 C5 H5A . . 119.3 ?
    C6 C5 H5A . . 118.7 ?
    C5 C6 C7 . . 125.8(6) ?
    C5 C6 C11 . . 116.7(7) ?
    C7 C6 C11 . . 117.5(7) ?
    C9 C7 C6 . . 117.8(7) ?
    C9 C7 C8 . . 121.5(7) ?
    C6 C7 C8 . . 120.7(7) ?
    C7 C8 H8A . . 110.0 ?
    C7 C8 H8B . . 109.2 ?
    H8A C8 H8B . . 109.5 ?
    C7 C9 C10 . . 120.5(7) ?
    C7 C9 H9A . . 119.7 ?
    C10 C9 H9A . . 119.8 ?
    N3 C10 C9 . . 123.2(7) ?
    N3 C10 C12 . . 117.7(6) ?
    C9 C10 C12 . . 119.1(7) ?
    N3 C11 N2 . . 115.5(6) ?
    N3 C11 C6 . . 124.0(7) ?
    N2 C11 C6 . . 120.5(7) ?
    C10 C12 Br1 . 7_565 110.6(3) ?
    C10 C12 Br1 . . 110.6(3) ?
    Br1 C12 Br1 7_565 . 110.3(3) ?
    C10 C12 H12A . . 108.2 ?
    Br1 C12 H12A 7_565 . 108.5 ?
    Br1 C12 H12A . . 108.5 ?
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
    C1 H1B F1 2 0.96 2.41 3.163(6) 135.4
