#------------------------------------------------------------------------------
#$Date: 2016-10-26 04:06:26 +0300 (Wed, 26 Oct 2016) $
#$Revision: 187564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/18/2241899.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2241899
loop_
_publ_author_name
'Wang, Bang Zhong'
'Zhou, Jun Ping'
'Zhou, Yong'
'Luo, Jian Song'
'Chi, Shao Ming'
_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
;
_journal_coeditor_code           WM5325
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1642
_journal_page_last               1644
_journal_paper_doi               10.1107/S2056989016016704
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C12 H10 B Br2 F2 N3 O'
_chemical_formula_moiety         'C12 H10 B Br2 F2 N3 O'
_chemical_formula_sum            'C12 H10 B Br2 F2 N3 O'
_chemical_formula_weight         420.86
_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
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.161(3)
_cell_length_b                   7.2169(14)
_cell_length_c                   11.678(2)
_cell_measurement_reflns_used    1765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.09
_cell_volume                     1446.3(5)
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_reduction
;
CrystalStructure (Rigaku/MSC, 2006)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL-97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1392
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13517
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    5.627
_exptl_absorpt_correction_T_max  0.3018
_exptl_absorpt_correction_T_min  0.2661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.366
_refine_ls_extinction_coef       0.0042(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0519P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                937
_reflns_number_total             1765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            wm5325sup1.cif
_cod_data_source_block           I
_cod_database_code               2241899
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'
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
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
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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
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_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

_cod_database_fobs_code 2241899
