#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:21:07 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179891 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/87/7018766.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_7018766
loop_
_publ_author_name
'Lakshmi, V.'
'Ravikanth, M.'
_publ_section_title
;
 Brominated boron dipyrrins: synthesis, structure, spectral and
 electrochemical properties
;
_journal_issue                   19
_journal_name_full               'Dalton Transactions'
_journal_page_first              5903
_journal_paper_doi               10.1039/c2dt00019a
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C16 H10 B Br3 F2 N2 O'
_chemical_formula_weight         534.80
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.580(7)
_cell_angle_beta                 92.262(7)
_cell_angle_gamma                106.758(9)
_cell_formula_units_Z            2
_cell_length_a                   8.2231(10)
_cell_length_b                   10.6391(10)
_cell_length_c                   10.7273(6)
_cell_measurement_reflns_used    3768
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.3188
_cell_measurement_theta_min      3.4685
_cell_volume                     858.64(15)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'OXFORD DIFFRACTION XCALIBUR-S'
_diffrn_measurement_method       ω/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6019
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    7.074
_exptl_absorpt_correction_T_max  0.3181
_exptl_absorpt_correction_T_min  0.2036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.069
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0298
_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)+(0.0485P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0777
_reflns_number_gt                2253
_reflns_number_total             3015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt00019a.txt
_cod_data_source_block           mr048
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        858.63(14)
_cod_database_code               7018766
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.00903(7) 0.18946(4) -0.44284(4) 0.06122(16) Uani 1 1 d .
Br2 Br 0.34174(6) -0.15593(4) 0.13177(4) 0.04999(15) Uani 1 1 d .
Br3 Br 0.21448(6) -0.21091(4) -0.20472(4) 0.05090(15) Uani 1 1 d .
F1 F 0.2593(3) 0.0589(2) -0.3090(2) 0.0434(5) Uani 1 1 d .
F2 F -0.0164(3) -0.02025(19) -0.2720(2) 0.0435(5) Uani 1 1 d .
O1 O 0.4180(4) 0.7026(2) 0.5255(2) 0.0492(7) Uani 1 1 d .
N1 N 0.1320(4) 0.2232(3) -0.1882(3) 0.0338(7) Uani 1 1 d .
N2 N 0.2048(4) 0.0584(3) -0.0906(3) 0.0324(7) Uani 1 1 d .
B1 B 0.1420(5) 0.0739(4) -0.2217(4) 0.0351(10) Uani 1 1 d .
C1 C 0.0717(5) 0.2813(4) -0.2689(4) 0.0410(9) Uani 1 1 d .
C2 C 0.0799(5) 0.4152(4) -0.2041(4) 0.0477(10) Uani 1 1 d .
H2 H 0.0455 0.4756 -0.2395 0.057 Uiso 1 1 calc R
C3 C 0.1482(5) 0.4410(4) -0.0783(4) 0.0409(9) Uani 1 1 d .
H3 H 0.1695 0.5230 -0.0122 0.049 Uiso 1 1 calc R
C4 C 0.1810(4) 0.3214(3) -0.0663(3) 0.0331(8) Uani 1 1 d .
C5 C 0.2415(4) 0.2926(3) 0.0424(3) 0.0310(8) Uani 1 1 d .
C6 C 0.2515(4) 0.1596(3) 0.0299(3) 0.0319(8) Uani 1 1 d .
C7 C 0.3095(5) 0.1067(4) 0.1225(4) 0.0360(8) Uani 1 1 d .
H7 H 0.3492 0.1525 0.2101 0.043 Uiso 1 1 calc R
C8 C 0.2960(4) -0.0276(3) 0.0576(4) 0.0358(9) Uani 1 1 d .
C9 C 0.2350(4) -0.0539(3) -0.0712(4) 0.0356(9) Uani 1 1 d .
C10 C 0.2949(4) 0.3989(3) 0.1701(3) 0.0331(8) Uani 1 1 d .
C11 C 0.4030(5) 0.5299(4) 0.1786(4) 0.0364(9) Uani 1 1 d .
H11 H 0.4441 0.5487 0.1038 0.044 Uiso 1 1 calc R
C12 C 0.4499(5) 0.6322(3) 0.2965(3) 0.0359(9) Uani 1 1 d .
H12 H 0.5247 0.7180 0.3010 0.043 Uiso 1 1 calc R
C13 C 0.3861(5) 0.6074(3) 0.4071(4) 0.0368(9) Uani 1 1 d .
C14 C 0.2833(5) 0.4757(4) 0.4003(4) 0.0427(10) Uani 1 1 d .
H14 H 0.2441 0.4569 0.4755 0.051 Uiso 1 1 calc R
C15 C 0.2394(5) 0.3739(4) 0.2844(4) 0.0387(9) Uani 1 1 d .
H15 H 0.1712 0.2864 0.2819 0.046 Uiso 1 1 calc R
C16 C 0.5047(6) 0.8416(4) 0.5298(4) 0.0581(12) Uani 1 1 d .
H16A H 0.6223 0.8516 0.5176 0.087 Uiso 1 1 calc R
H16B H 0.4991 0.9019 0.6129 0.087 Uiso 1 1 calc R
H16C H 0.4507 0.8646 0.4618 0.087 Uiso 1 1 calc R
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
C13 O1 C16 116.7(3)
C1 N1 C4 106.8(3)
C1 N1 B1 127.2(3)
C4 N1 B1 126.0(3)
C9 N2 C6 106.3(3)
C9 N2 B1 126.7(3)
C6 N2 B1 126.9(3)
F2 B1 F1 110.8(3)
F2 B1 N2 110.4(3)
F1 B1 N2 110.3(3)
F2 B1 N1 110.8(3)
F1 B1 N1 109.4(3)
N2 B1 N1 105.1(3)
N1 C1 C2 111.0(4)
N1 C1 Br1 122.6(3)
C2 C1 Br1 126.3(3)
C3 C2 C1 106.6(3)
C3 C2 H2 126.7
C1 C2 H2 126.7
C2 C3 C4 108.0(3)
C2 C3 H3 126.0
C4 C3 H3 126.0
C5 C4 N1 121.9(3)
C5 C4 C3 130.6(3)
N1 C4 C3 107.4(3)
C4 C5 C6 119.2(3)
C4 C5 C10 120.9(3)
C6 C5 C10 119.8(3)
C7 C6 N2 109.2(3)
C7 C6 C5 130.0(3)
N2 C6 C5 120.7(3)
C8 C7 C6 106.0(3)
C8 C7 H7 127.0
C6 C7 H7 127.0
C9 C8 C7 108.4(3)
C9 C8 Br2 125.2(3)
C7 C8 Br2 126.4(3)
N2 C9 C8 110.1(3)
N2 C9 Br3 123.2(3)
C8 C9 Br3 126.5(3)
C15 C10 C11 117.9(3)
C15 C10 C5 122.1(3)
C11 C10 C5 120.1(3)
C12 C11 C10 121.0(3)
C12 C11 H11 119.5
C10 C11 H11 119.5
C13 C12 C11 120.2(3)
C13 C12 H12 119.9
C11 C12 H12 119.9
O1 C13 C12 124.5(3)
O1 C13 C14 116.4(3)
C12 C13 C14 119.0(3)
C15 C14 C13 120.8(3)
C15 C14 H14 119.6
C13 C14 H14 119.6
C14 C15 C10 121.0(3)
C14 C15 H15 119.5
C10 C15 H15 119.5
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.851(4)
Br2 C8 1.869(3)
Br3 C9 1.844(4)
F1 B1 1.383(5)
F2 B1 1.376(5)
O1 C13 1.355(4)
O1 C16 1.432(4)
N1 C1 1.345(5)
N1 C4 1.395(4)
N1 B1 1.559(5)
N2 C9 1.354(4)
N2 C6 1.397(4)
N2 B1 1.545(5)
C1 C2 1.387(5)
C2 C3 1.366(6)
C2 H2 0.9300
C3 C4 1.411(5)
C3 H3 0.9300
C4 C5 1.391(5)
C5 C6 1.411(5)
C5 C10 1.477(5)
C6 C7 1.397(5)
C7 C8 1.380(5)
C7 H7 0.9300
C8 C9 1.377(5)
C10 C15 1.389(5)
C10 C11 1.398(5)
C11 C12 1.383(5)
C11 H11 0.9300
C12 C13 1.374(5)
C12 H12 0.9300
C13 C14 1.393(5)
C14 C15 1.366(5)
C14 H14 0.9300
C15 H15 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
C9 N2 B1 F2 61.4(5)
C6 N2 B1 F2 -122.8(3)
C9 N2 B1 F1 -61.3(4)
C6 N2 B1 F1 114.5(4)
C9 N2 B1 N1 -179.1(3)
C6 N2 B1 N1 -3.3(5)
C1 N1 B1 F2 -55.5(5)
C4 N1 B1 F2 122.9(3)
C1 N1 B1 F1 66.9(5)
C4 N1 B1 F1 -114.7(4)
C1 N1 B1 N2 -174.7(3)
C4 N1 B1 N2 3.7(5)
C4 N1 C1 C2 0.2(4)
B1 N1 C1 C2 178.8(3)
C4 N1 C1 Br1 180.0(3)
B1 N1 C1 Br1 -1.4(5)
N1 C1 C2 C3 0.1(5)
Br1 C1 C2 C3 -179.7(3)
C1 C2 C3 C4 -0.3(5)
C1 N1 C4 C5 176.7(3)
B1 N1 C4 C5 -2.0(5)
C1 N1 C4 C3 -0.4(4)
B1 N1 C4 C3 -179.1(3)
C2 C3 C4 C5 -176.3(4)
C2 C3 C4 N1 0.5(4)
N1 C4 C5 C6 -0.9(5)
C3 C4 C5 C6 175.4(4)
N1 C4 C5 C10 179.2(3)
C3 C4 C5 C10 -4.5(6)
C9 N2 C6 C7 -0.3(4)
B1 N2 C6 C7 -176.8(3)
C9 N2 C6 C5 177.7(3)
B1 N2 C6 C5 1.2(5)
C4 C5 C6 C7 178.8(4)
C10 C5 C6 C7 -1.3(6)
C4 C5 C6 N2 1.3(5)
C10 C5 C6 N2 -178.8(3)
N2 C6 C7 C8 -0.6(4)
C5 C6 C7 C8 -178.3(4)
C6 C7 C8 C9 1.2(4)
C6 C7 C8 Br2 -176.0(3)
C6 N2 C9 C8 1.1(4)
B1 N2 C9 C8 177.6(3)
C6 N2 C9 Br3 -173.6(2)
B1 N2 C9 Br3 2.9(5)
C7 C8 C9 N2 -1.5(4)
Br2 C8 C9 N2 175.8(2)
C7 C8 C9 Br3 173.0(3)
Br2 C8 C9 Br3 -9.7(5)
C4 C5 C10 C15 131.7(4)
C6 C5 C10 C15 -48.2(5)
C4 C5 C10 C11 -47.6(5)
C6 C5 C10 C11 132.5(4)
C15 C10 C11 C12 -1.5(5)
C5 C10 C11 C12 177.8(3)
C10 C11 C12 C13 -2.0(6)
C16 O1 C13 C12 8.8(6)
C16 O1 C13 C14 -172.2(4)
C11 C12 C13 O1 -176.8(3)
C11 C12 C13 C14 4.2(6)
O1 C13 C14 C15 177.9(3)
C12 C13 C14 C15 -3.1(6)
C13 C14 C15 C10 -0.4(6)
C11 C10 C15 C14 2.7(5)
C5 C10 C15 C14 -176.6(3)
