#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/84/2228468.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228468
loop_
_publ_author_name
'Morse, Graham E.'
'Maka, Jozef F.'
'Lough, Alan J.'
'Bender, Timothy P.'
_publ_section_title
;
 Bromido(dodecafluorosubphthalocyaninato)boron(III)
;
_journal_coeditor_code           NC2200
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3057
_journal_page_last               o3058
_journal_paper_doi               10.1107/S1600536810041863
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C24 B Br F12 N6'
_chemical_formula_moiety         'C24 B Br F12 N6'
_chemical_formula_sum            'C24 B Br F12 N6'
_chemical_formula_weight         691.02
_chemical_name_common
;
Bromido(dodecafluorosubphthalocyaninato)boron
Bromododecafluoroboronsubphthalocyanine
;
_chemical_name_systematic
;
Bromido(1,2,3,4,8,9,10,11,15,16,17,18-dodecafluoro-7,12:14,19-diimino-
21,5-nitrilo-5H-tribenzo[c,h,m][1,6,11]triazacyclopentadecinato)boron(III)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.2270(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1681(5)
_cell_length_b                   10.8858(2)
_cell_length_c                   19.0664(7)
_cell_measurement_reflns_used    15166
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     2308.33(14)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15166
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    1.909
_exptl_absorpt_correction_T_max  0.835
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SORTAV; Blessing, 1995)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.949
_refine_diff_density_min         -0.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                3728
_reflns_number_total             5263
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2200.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228468
_cod_database_fobs_code          2228468
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
Br Br1 0.54911(3) 0.40086(2) 0.211746(16) 0.02854(12) Uani d . 1 . .
F F1 0.52166(15) 0.13977(15) 0.52612(9) 0.0308(4) Uani d . 1 . .
F F2 0.31173(16) 0.13286(16) 0.58691(9) 0.0335(4) Uani d . 1 . .
F F3 0.09951(16) 0.16152(16) 0.51060(10) 0.0364(5) Uani d . 1 . .
F F4 0.08838(15) 0.18422(15) 0.36791(9) 0.0302(4) Uani d . 1 . .
F F5 0.05945(15) 0.06664(17) 0.12934(10) 0.0365(4) Uani d . 1 . .
F F6 0.04016(16) -0.11128(16) 0.02786(11) 0.0411(5) Uani d . 1 . .
F F7 0.23599(17) -0.19317(16) -0.02953(10) 0.0401(5) Uani d . 1 . .
F F8 0.45774(15) -0.11084(14) 0.01579(9) 0.0282(4) Uani d . 1 . .
F F9 0.85617(15) -0.07367(15) 0.13742(10) 0.0326(4) Uani d . 1 . .
F F10 1.04672(16) -0.14952(18) 0.22740(11) 0.0444(5) Uani d . 1 . .
F F11 1.06140(16) -0.08814(17) 0.36440(11) 0.0442(5) Uani d . 1 . .
F F12 0.88979(15) 0.05387(16) 0.41661(9) 0.0352(4) Uani d . 1 . .
N N1 0.4472(2) 0.2141(2) 0.30191(12) 0.0218(5) Uani d . 1 . .
N N2 0.2545(2) 0.1752(2) 0.24173(12) 0.0231(5) Uani d . 1 . .
N N3 0.4328(2) 0.1592(2) 0.18160(13) 0.0217(5) Uani d . 1 . .
N N4 0.5946(2) 0.0451(2) 0.13988(13) 0.0231(5) Uani d . 1 . .
N N5 0.6199(2) 0.1505(2) 0.24953(12) 0.0213(5) Uani d . 1 . .
N N6 0.6238(2) 0.1572(2) 0.37443(13) 0.0239(6) Uani d . 1 . .
C C1 0.5068(3) 0.1882(2) 0.36615(16) 0.0235(6) Uani d . 1 . .
C C2 0.4140(3) 0.1777(2) 0.41463(15) 0.0221(6) Uani d . 1 . .
C C3 0.4175(3) 0.1550(3) 0.48641(16) 0.0243(7) Uani d . 1 . .
C C4 0.3113(3) 0.1491(3) 0.51729(16) 0.0273(7) Uani d . 1 . .
C C5 0.2002(3) 0.1616(3) 0.47737(17) 0.0271(7) Uani d . 1 . .
C C6 0.1951(3) 0.1764(2) 0.40552(16) 0.0244(7) Uani d . 1 . .
C C7 0.3015(3) 0.1865(2) 0.37388(16) 0.0235(6) Uani d . 1 . .
C C8 0.3254(3) 0.1999(2) 0.30061(16) 0.0228(6) Uani d . 1 . .
C C9 0.3109(3) 0.1472(2) 0.18449(15) 0.0220(6) Uani d . 1 . .
C C10 0.2697(3) 0.0688(3) 0.12508(16) 0.0235(6) Uani d . 1 . .
C C11 0.1577(3) 0.0248(3) 0.10206(16) 0.0283(7) Uani d . 1 . .
C C12 0.1472(3) -0.0642(3) 0.05019(17) 0.0313(7) Uani d . 1 . .
C C13 0.2494(3) -0.1071(3) 0.02084(16) 0.0278(7) Uani d . 1 . .
C C14 0.3619(3) -0.0637(3) 0.04319(15) 0.0249(7) Uani d . 1 . .
C C15 0.3744(3) 0.0259(2) 0.09517(15) 0.0226(6) Uani d . 1 . .
C C16 0.4785(3) 0.0802(2) 0.13529(15) 0.0222(6) Uani d . 1 . .
C C17 0.6618(3) 0.0783(2) 0.19883(16) 0.0220(6) Uani d . 1 . .
C C18 0.7745(3) 0.0277(3) 0.23143(16) 0.0247(7) Uani d . 1 . .
C C19 0.8630(3) -0.0444(3) 0.20584(17) 0.0276(7) Uani d . 1 . .
C C20 0.9576(3) -0.0830(3) 0.25135(19) 0.0326(8) Uani d . 1 . .
C C21 0.9660(3) -0.0509(3) 0.32254(19) 0.0324(8) Uani d . 1 . .
C C22 0.8793(3) 0.0217(3) 0.34902(17) 0.0289(7) Uani d . 1 . .
C C23 0.7829(3) 0.0615(3) 0.30424(16) 0.0238(6) Uani d . 1 . .
C C24 0.6767(3) 0.1334(2) 0.31523(15) 0.0217(6) Uani d . 1 . .
B B1 0.5091(3) 0.2236(3) 0.23690(17) 0.0218(7) Uani d . 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'
B B 0.0013 0.0007 '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'
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
C8 N1 C1 . . 113.3(2) ?
C8 N1 B1 . . 122.3(3) ?
C1 N1 B1 . . 122.6(2) ?
C8 N2 C9 . . 116.1(2) ?
C16 N3 C9 . . 113.4(2) ?
C16 N3 B1 . . 122.5(2) ?
C9 N3 B1 . . 121.9(2) ?
C17 N4 C16 . . 116.0(2) ?
C17 N5 C24 . . 114.3(2) ?
C17 N5 B1 . . 122.3(2) ?
C24 N5 B1 . . 122.5(2) ?
C1 N6 C24 . . 116.5(2) ?
N6 C1 N1 . . 123.0(3) ?
N6 C1 C2 . . 130.3(3) ?
N1 C1 C2 . . 105.6(2) ?
C3 C2 C7 . . 119.7(3) ?
C3 C2 C1 . . 133.1(3) ?
C7 C2 C1 . . 107.1(3) ?
F1 C3 C4 . . 119.4(3) ?
F1 C3 C2 . . 121.6(3) ?
C4 C3 C2 . . 118.9(3) ?
F2 C4 C3 . . 120.4(3) ?
F2 C4 C5 . . 118.3(3) ?
C3 C4 C5 . . 121.3(3) ?
F3 C5 C6 . . 120.7(3) ?
F3 C5 C4 . . 118.9(3) ?
C6 C5 C4 . . 120.5(3) ?
F4 C6 C5 . . 119.8(3) ?
F4 C6 C7 . . 121.3(3) ?
C5 C6 C7 . . 118.9(3) ?
C6 C7 C2 . . 120.6(3) ?
C6 C7 C8 . . 131.8(3) ?
C2 C7 C8 . . 107.5(2) ?
N2 C8 N1 . . 123.3(3) ?
N2 C8 C7 . . 129.6(3) ?
N1 C8 C7 . . 105.3(3) ?
N2 C9 N3 . . 123.4(3) ?
N2 C9 C10 . . 128.6(3) ?
N3 C9 C10 . . 105.6(2) ?
C11 C10 C15 . . 120.9(3) ?
C11 C10 C9 . . 131.8(3) ?
C15 C10 C9 . . 106.9(2) ?
F5 C11 C10 . . 120.9(3) ?
F5 C11 C12 . . 119.9(3) ?
C10 C11 C12 . . 119.3(3) ?
F6 C12 C11 . . 120.9(3) ?
F6 C12 C13 . . 119.0(3) ?
C11 C12 C13 . . 120.1(3) ?
F7 C13 C14 . . 120.1(3) ?
F7 C13 C12 . . 118.6(3) ?
C14 C13 C12 . . 121.2(3) ?
F8 C14 C13 . . 119.3(3) ?
F8 C14 C15 . . 121.1(3) ?
C13 C14 C15 . . 119.5(3) ?
C14 C15 C10 . . 118.9(3) ?
C14 C15 C16 . . 133.1(3) ?
C10 C15 C16 . . 107.5(2) ?
N4 C16 N3 . . 123.5(3) ?
N4 C16 C15 . . 129.5(3) ?
N3 C16 C15 . . 105.5(2) ?
N4 C17 N5 . . 123.2(3) ?
N4 C17 C18 . . 130.5(3) ?
N5 C17 C18 . . 104.7(2) ?
C19 C18 C23 . . 120.1(3) ?
C19 C18 C17 . . 132.8(3) ?
C23 C18 C17 . . 107.1(2) ?
F9 C19 C20 . . 121.0(3) ?
F9 C19 C18 . . 120.0(3) ?
C20 C19 C18 . . 119.0(3) ?
F10 C20 C19 . . 120.2(3) ?
F10 C20 C21 . . 118.6(3) ?
C19 C20 C21 . . 121.2(3) ?
F11 C21 C22 . . 120.2(3) ?
F11 C21 C20 . . 119.0(3) ?
C22 C21 C20 . . 120.8(3) ?
F12 C22 C21 . . 120.1(3) ?
F12 C22 C23 . . 120.7(3) ?
C21 C22 C23 . . 119.1(3) ?
C22 C23 C18 . . 119.8(3) ?
C22 C23 C24 . . 132.9(3) ?
C18 C23 C24 . . 107.3(3) ?
N6 C24 N5 . . 122.7(3) ?
N6 C24 C23 . . 130.7(3) ?
N5 C24 C23 . . 105.0(2) ?
N3 B1 N5 . . 106.4(2) ?
N3 B1 N1 . . 106.4(2) ?
N5 B1 N1 . . 106.0(2) ?
N3 B1 Br1 . . 113.9(2) ?
N5 B1 Br1 . . 110.5(2) ?
N1 B1 Br1 . . 113.1(2) ?
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 B1 . 2.047(3) ?
F1 C3 . 1.339(3) ?
F2 C4 . 1.339(3) ?
F3 C5 . 1.340(3) ?
F4 C6 . 1.336(3) ?
F5 C11 . 1.337(3) ?
F6 C12 . 1.334(3) ?
F7 C13 . 1.340(3) ?
F8 C14 . 1.336(3) ?
F9 C19 . 1.338(4) ?
F10 C20 . 1.344(4) ?
F11 C21 . 1.335(4) ?
F12 C22 . 1.330(3) ?
N1 C8 . 1.366(4) ?
N1 C1 . 1.369(4) ?
N1 B1 . 1.477(4) ?
N2 C8 . 1.341(4) ?
N2 C9 . 1.344(4) ?
N3 C16 . 1.365(4) ?
N3 C9 . 1.373(4) ?
N3 B1 . 1.472(4) ?
N4 C17 . 1.343(4) ?
N4 C16 . 1.347(4) ?
N5 C17 . 1.361(4) ?
N5 C24 . 1.364(4) ?
N5 B1 . 1.472(4) ?
N6 C1 . 1.345(4) ?
N6 C24 . 1.346(4) ?
C1 C2 . 1.454(4) ?
C2 C3 . 1.388(4) ?
C2 C7 . 1.419(4) ?
C3 C4 . 1.373(4) ?
C4 C5 . 1.402(4) ?
C5 C6 . 1.376(4) ?
C6 C7 . 1.385(4) ?
C7 C8 . 1.454(4) ?
C9 C10 . 1.459(4) ?
C10 C11 . 1.373(4) ?
C10 C15 . 1.425(4) ?
C11 C12 . 1.381(4) ?
C12 C13 . 1.397(4) ?
C13 C14 . 1.373(4) ?
C14 C15 . 1.388(4) ?
C15 C16 . 1.458(4) ?
C17 C18 . 1.460(4) ?
C18 C19 . 1.385(4) ?
C18 C23 . 1.431(4) ?
C19 C20 . 1.371(4) ?
C20 C21 . 1.396(5) ?
C21 C22 . 1.381(4) ?
C22 C23 . 1.382(4) ?
C23 C24 . 1.451(4) ?
