#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/54/2225426.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_2225426
loop_
_publ_author_name
'Zhou, XiaoFeng'
_publ_section_title
;
 4,4-Difluoro-1,3,5,7-tetramethyl-8-pentafluorophenyl-4-bora-3a,4a-diaza-s-indacene
;
_journal_coeditor_code           BH2269
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o757
_journal_paper_doi               10.1107/S1600536810003703
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H14 B F7 N2'
_chemical_formula_moiety         'C19 H14 B F7 N2'
_chemical_formula_sum            'C19 H14 B F7 N2'
_chemical_formula_weight         414.13
_chemical_name_systematic
;
4,4-Difluoro-1,3,5,7-tetramethyl-8-pentafluorophenyl-4-bora-3a,4a-diaza-
s-indacene
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_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(4)
_cell_angle_beta                 97.12(2)
_cell_angle_gamma                90.00(15)
_cell_formula_units_Z            4
_cell_length_a                   12.4060(5)
_cell_length_b                   7.5490(9)
_cell_length_c                   19.720(3)
_cell_measurement_reflns_used    2191
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4642
_cell_measurement_theta_min      3.1225
_cell_volume                     1832.6(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8232
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     170
_refine_ls_number_reflns         1936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0564
_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)+(0.0910P)²+0.8854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1619
_reflns_number_gt                1585
_reflns_number_total             1936
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2269.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2225426
_cod_database_fobs_code          2225426
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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_disorder_assembly
_atom_site_disorder_group
F F1 0.12945(15) 0.3502(3) 0.07469(8) 0.1040(7) Uani d . 1 . .
F F3 0.28302(13) 0.18847(16) 0.34101(7) 0.0721(5) Uani d . 1 . .
F F4 0.35839(14) 0.1888(2) 0.47541(8) 0.0928(6) Uani d . 1 . .
F F5 0.39356(18) 0.5000 0.54333(9) 0.0988(9) Uani d S 1 . .
N N1 0.08602(19) 0.5000 0.17499(11) 0.0486(6) Uani d S 1 . .
N N2 0.2747(2) 0.5000 0.14360(11) 0.0523(6) Uani d S 1 . .
C C1 -0.0234(2) 0.5000 0.17144(15) 0.0564(7) Uani d S 1 . .
C C2 -0.0523(2) 0.5000 0.23784(16) 0.0597(8) Uani d S 1 . .
H H2A -0.1229 0.5000 0.2490 0.104(14) Uiso d SR 1 . .
C C3 0.0406(2) 0.5000 0.28399(14) 0.0489(7) Uani d S 1 . .
C C4 0.1291(2) 0.5000 0.24405(12) 0.0446(6) Uani d S 1 . .
C C5 0.2418(2) 0.5000 0.26194(12) 0.0422(6) Uani d S 1 . .
C C6 0.3151(2) 0.5000 0.21363(13) 0.0475(6) Uani d S 1 . .
C C7 0.4316(2) 0.5000 0.21939(16) 0.0563(7) Uani d S 1 . .
C C8 0.4565(3) 0.5000 0.15330(17) 0.0682(9) Uani d S 1 . .
H H8A 0.5263 0.5000 0.1408 0.080(11) Uiso d SR 1 . .
C C9 0.3606(3) 0.5000 0.10769(15) 0.0627(8) Uani d S 1 . .
C C10 -0.0981(3) 0.5000 0.10532(18) 0.0783(11) Uani d S 1 . .
H H10A -0.0559 0.5000 0.0677 0.16(2) Uiso d SR 1 . .
H H10B -0.1430 0.6038 0.1031 0.23(3) Uiso d R 1 . .
C C11 0.0428(3) 0.5000 0.36050(15) 0.0629(9) Uani d S 1 . .
H H11A -0.0302 0.5000 0.3719 0.079(11) Uiso d SR 1 . .
H H11B 0.0801 0.6038 0.3792 0.093(9) Uiso d R 1 . .
C C12 0.3492(4) 0.5000 0.03121(18) 0.0875(13) Uani d S 1 . .
H H12A 0.2735 0.5000 0.0135 0.25(4) Uiso d SR 1 . .
H H12B 0.3833 0.3962 0.0156 0.172(19) Uiso d R 1 . .
C C13 0.5127(3) 0.5000 0.28225(19) 0.0693(9) Uani d S 1 . .
H H13A 0.5847 0.5000 0.2693 0.126(17) Uiso d SR 1 . .
H H13B 0.5027 0.3962 0.3089 0.129(13) Uiso d R 1 . .
C C14 0.2846(2) 0.5000 0.33641(13) 0.0425(6) Uani d S 1 . .
C C15 0.30342(16) 0.3443(3) 0.37278(10) 0.0490(5) Uani d . 1 . .
C C16 0.34105(17) 0.3429(3) 0.44160(11) 0.0602(6) Uani d . 1 . .
C C17 0.3592(2) 0.5000 0.47584(15) 0.0638(9) Uani d S 1 . .
B B1 0.1532(3) 0.5000 0.11399(17) 0.0612(9) Uani d S 1 . .
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'
F F 0.0171 0.0103 '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'
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
C1 N1 C4 . . 108.1(2) ?
C1 N1 B1 . . 126.5(2) ?
C4 N1 B1 . . 125.4(2) ?
C9 N2 C6 . . 107.8(3) ?
C9 N2 B1 . . 126.6(3) ?
C6 N2 B1 . . 125.5(2) ?
N1 C1 C2 . . 108.9(3) ?
N1 C1 C10 . . 123.6(3) ?
C2 C1 C10 . . 127.6(3) ?
C3 C2 C1 . . 109.2(3) ?
C3 C2 H2A . . 125.5 ?
C1 C2 H2A . . 125.4 ?
C2 C3 C4 . . 105.8(2) ?
C2 C3 C11 . . 124.9(3) ?
C4 C3 C11 . . 129.2(3) ?
N1 C4 C5 . . 119.6(2) ?
N1 C4 C3 . . 108.0(2) ?
C5 C4 C3 . . 132.3(2) ?
C6 C5 C4 . . 122.9(2) ?
C6 C5 C14 . . 119.1(2) ?
C4 C5 C14 . . 118.0(2) ?
C5 C6 N2 . . 119.1(2) ?
C5 C6 C7 . . 132.9(3) ?
N2 C6 C7 . . 108.0(2) ?
C8 C7 C6 . . 105.5(3) ?
C8 C7 C13 . . 125.3(3) ?
C6 C7 C13 . . 129.2(3) ?
C7 C8 C9 . . 109.6(3) ?
C7 C8 H8A . . 125.2 ?
C9 C8 H8A . . 125.1 ?
N2 C9 C8 . . 109.0(3) ?
N2 C9 C12 . . 123.1(3) ?
C8 C9 C12 . . 127.9(3) ?
C1 C10 H10A . . 109.6 ?
C1 C10 H10B . . 109.4 ?
H10A C10 H10B . . 109.5 ?
C3 C11 H11A . . 109.5 ?
C3 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C7 C13 H13A . . 109.4 ?
C7 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C15 C14 C15 . 6_565 116.6(2) ?
C15 C14 C5 . . 121.69(13) ?
C15 C14 C5 6_565 . 121.69(13) ?
F3 C15 C14 . . 119.56(18) ?
F3 C15 C16 . . 118.27(19) ?
C14 C15 C16 . . 122.2(2) ?
F4 C16 C17 . . 119.9(2) ?
F4 C16 C15 . . 120.6(2) ?
C17 C16 C15 . . 119.5(2) ?
F5 C17 C16 . . 119.99(14) ?
F5 C17 C16 . 6_565 119.99(14) ?
C16 C17 C16 . 6_565 120.0(3) ?
F1 B1 F1 . 6_565 109.8(3) yes
N1 B1 N2 . . 107.5(2) yes
F1 B1 N1 . . 109.8(2) yes
F1 B1 N1 6_565 . 109.8(2) yes
F1 B1 N2 . . 110.0(2) yes
F1 B1 N2 6_565 . 110.0(2) yes
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
B1 F1 . 1.382(3) yes
B1 N1 . 1.546(4) yes
B1 N2 . 1.548(5) yes
F3 C15 . 1.342(3) ?
F4 C16 . 1.345(3) ?
F5 C17 . 1.346(3) ?
N1 C1 . 1.350(4) ?
N1 C4 . 1.400(3) ?
N2 C9 . 1.350(4) ?
N2 C6 . 1.409(4) ?
C1 C2 . 1.400(4) ?
C1 C10 . 1.503(4) ?
C2 C3 . 1.377(4) ?
C2 H2A . 0.9298 ?
C3 C4 . 1.428(4) ?
C3 C11 . 1.506(4) ?
C4 C5 . 1.398(4) ?
C5 C6 . 1.397(4) ?
C5 C14 . 1.498(3) ?
C6 C7 . 1.435(4) ?
C7 C8 . 1.376(4) ?
C7 C13 . 1.497(5) ?
C8 C9 . 1.400(5) ?
C8 H8A . 0.9301 ?
C9 C12 . 1.497(4) ?
C10 H10A . 0.9598 ?
C10 H10B . 0.9600 ?
C11 H11A . 0.9601 ?
C11 H11B . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9601 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C14 C15 . 1.382(2) ?
C14 C15 6_565 1.382(2) ?
C15 C16 . 1.379(3) ?
C16 C17 . 1.370(3) ?
C17 C16 6_565 1.370(3) ?
B1 F1 6_565 1.382(3) ?
