#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:21:07 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179891 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/87/7018764.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_7018764
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 H9 B Br4 F2 N2 O'
_chemical_formula_weight         613.70
_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                73.442(4)
_cell_angle_beta                 74.044(4)
_cell_angle_gamma                84.062(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8922(4)
_cell_length_b                   11.1893(6)
_cell_length_c                   11.3508(5)
_cell_measurement_reflns_used    4668
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.7252
_cell_measurement_theta_min      3.6873
_cell_volume                     923.44(8)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10011
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         32.80
_diffrn_reflns_theta_min         3.69
_exptl_absorpt_coefficient_mu    8.744
_exptl_absorpt_correction_T_max  0.2611
_exptl_absorpt_correction_T_min  0.1605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    2.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.497
_refine_diff_density_min         -1.225
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0391
_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)+(0.0348P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                4622
_reflns_number_total             6014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt00019a.txt
_cod_data_source_block           mr043a
_cod_database_code               7018764
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
B1 B 0.7511(4) 0.0046(3) 0.6953(4) 0.0209(7) Uani 1 1 d .
Br1 Br 0.83020(5) 0.11311(3) 0.91808(3) 0.03386(10) Uani 1 1 d .
Br2 Br 0.90625(5) 0.43872(3) 0.77205(4) 0.03204(10) Uani 1 1 d .
Br3 Br 0.69920(4) -0.20837(3) 0.32831(4) 0.02844(9) Uani 1 1 d .
Br4 Br 0.75454(4) -0.27080(3) 0.64063(4) 0.02917(9) Uani 1 1 d .
F1 F 0.5941(2) -0.03271(16) 0.78029(18) 0.0267(4) Uani 1 1 d .
F2 F 0.8904(2) -0.06378(16) 0.7347(2) 0.0279(4) Uani 1 1 d .
N1 N 0.7786(3) 0.1461(2) 0.6732(2) 0.0195(5) Uani 1 1 d .
N2 N 0.7521(3) -0.0083(2) 0.5611(3) 0.0187(5) Uani 1 1 d .
O1 O 0.7166(3) 0.5938(2) 0.0149(2) 0.0327(6) Uani 1 1 d .
C1 C 0.8167(4) 0.2002(3) 0.7553(3) 0.0213(6) Uani 1 1 d .
C2 C 0.8414(4) 0.3280(3) 0.6981(3) 0.0212(6) Uani 1 1 d .
C3 C 0.8160(4) 0.3535(3) 0.5781(3) 0.0191(6) Uani 1 1 d .
H3 H 0.8246 0.4324 0.5171 0.023 Uiso 1 1 calc R
C4 C 0.7750(4) 0.2407(3) 0.5629(3) 0.0178(6) Uani 1 1 d .
C5 C 0.7476(4) 0.2137(3) 0.4563(3) 0.0178(6) Uani 1 1 d .
C6 C 0.7328(4) 0.0897(3) 0.4574(3) 0.0183(6) Uani 1 1 d .
C7 C 0.7066(4) 0.0400(3) 0.3626(3) 0.0207(6) Uani 1 1 d .
H7 H 0.6883 0.0856 0.2824 0.025 Uiso 1 1 calc R
C8 C 0.7130(4) -0.0881(3) 0.4100(3) 0.0226(6) Uani 1 1 d .
C9 C 0.7395(4) -0.1139(3) 0.5314(3) 0.0208(6) Uani 1 1 d .
C10 C 0.7382(4) 0.3157(3) 0.3430(3) 0.0169(6) Uani 1 1 d .
C11 C 0.8405(4) 0.3101(3) 0.2229(3) 0.0200(6) Uani 1 1 d .
H11 H 0.9185 0.2407 0.2145 0.024 Uiso 1 1 calc R
C12 C 0.8291(4) 0.4042(3) 0.1165(3) 0.0234(6) Uani 1 1 d .
H12 H 0.9002 0.3997 0.0354 0.028 Uiso 1 1 calc R
C13 C 0.7140(4) 0.5063(3) 0.1266(3) 0.0225(6) Uani 1 1 d .
C14 C 0.6121(4) 0.5132(3) 0.2443(3) 0.0206(6) Uani 1 1 d .
H14 H 0.5332 0.5824 0.2516 0.025 Uiso 1 1 calc R
C15 C 0.6242(4) 0.4191(3) 0.3526(3) 0.0193(6) Uani 1 1 d .
H15 H 0.5546 0.4249 0.4337 0.023 Uiso 1 1 calc R
C16 C 0.5955(6) 0.6983(4) 0.0193(4) 0.0491(11) Uani 1 1 d .
H16A H 0.4744 0.6687 0.0513 0.074 Uiso 1 1 calc R
H16B H 0.6109 0.7548 -0.0664 0.074 Uiso 1 1 calc R
H16C H 0.6185 0.7428 0.0760 0.074 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'
O O 0.0106 0.0060 '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'
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'
B B 0.0013 0.0007 '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
_geom_angle_site_symmetry_3
F1 B1 F2 111.4(3) .
F1 B1 N1 111.4(3) .
F2 B1 N1 109.4(2) .
F1 B1 N2 110.2(2) .
F2 B1 N2 109.6(3) .
N1 B1 N2 104.6(2) .
C2 Br2 Br4 107.85(9) 1_565
C1 N1 C4 106.9(2) .
C1 N1 B1 126.8(3) .
C4 N1 B1 126.3(3) .
C9 N2 C6 106.8(3) .
C9 N2 B1 126.6(3) .
C6 N2 B1 125.6(2) .
C13 O1 C16 117.2(3) .
N1 C1 C2 109.7(3) .
N1 C1 Br1 123.3(2) .
C2 C1 Br1 127.0(2) .
C3 C2 C1 107.6(3) .
C3 C2 Br2 127.4(2) .
C1 C2 Br2 124.9(2) .
C2 C3 C4 107.0(3) .
C2 C3 H3 126.5 .
C4 C3 H3 126.5 .
N1 C4 C3 108.8(3) .
N1 C4 C5 120.9(3) .
C3 C4 C5 130.0(3) .
C6 C5 C4 119.9(3) .
C6 C5 C10 120.3(3) .
C4 C5 C10 119.8(3) .
N2 C6 C5 120.9(3) .
N2 C6 C7 108.8(3) .
C5 C6 C7 130.2(3) .
C8 C7 C6 106.2(3) .
C8 C7 H7 126.9 .
C6 C7 H7 126.9 .
C7 C8 C9 107.4(3) .
C7 C8 Br3 127.8(3) .
C9 C8 Br3 124.8(2) .
N2 C9 C8 110.7(3) .
N2 C9 Br4 123.1(2) .
C8 C9 Br4 126.1(2) .
C11 C10 C15 118.6(3) .
C11 C10 C5 120.5(3) .
C15 C10 C5 120.9(3) .
C12 C11 C10 120.5(3) .
C12 C11 H11 119.7 .
C10 C11 H11 119.7 .
C11 C12 C13 120.6(3) .
C11 C12 H12 119.7 .
C13 C12 H12 119.7 .
O1 C13 C14 125.4(3) .
O1 C13 C12 115.0(3) .
C14 C13 C12 119.6(3) .
C13 C14 C15 120.1(3) .
C13 C14 H14 119.9 .
C15 C14 H14 119.9 .
C14 C15 C10 120.5(3) .
C14 C15 H15 119.7 .
C10 C15 H15 119.7 .
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
_geom_bond_site_symmetry_2
B1 F1 1.364(4) .
B1 F2 1.377(4) .
B1 N1 1.559(4) .
B1 N2 1.568(5) .
Br1 C1 1.853(3) .
Br2 C2 1.861(3) .
Br2 Br4 3.4112(5) 1_565
Br3 C8 1.865(3) .
Br4 C9 1.852(3) .
N1 C1 1.356(4) .
N1 C4 1.395(4) .
N2 C9 1.338(4) .
N2 C6 1.393(4) .
O1 C13 1.359(4) .
O1 C16 1.435(4) .
C1 C2 1.401(4) .
C2 C3 1.376(4) .
C3 C4 1.402(4) .
C3 H3 0.9500 .
C4 C5 1.402(4) .
C5 C6 1.401(4) .
C5 C10 1.470(4) .
C6 C7 1.413(4) .
C7 C8 1.381(4) .
C7 H7 0.9500 .
C8 C9 1.395(5) .
C10 C11 1.395(4) .
C10 C15 1.401(4) .
C11 C12 1.375(4) .
C11 H11 0.9500 .
C12 C13 1.395(4) .
C12 H12 0.9500 .
C13 C14 1.376(5) .
C14 C15 1.392(4) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 F2 0.95 2.40 3.307(3) 160.8 2_756
C12 H12 Br2 0.95 2.88 3.699(3) 144.8 1_554
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
_geom_torsion_site_symmetry_1
F1 B1 N1 C1 72.9(4) .
F2 B1 N1 C1 -50.7(4) .
N2 B1 N1 C1 -168.0(3) .
F1 B1 N1 C4 -109.6(3) .
F2 B1 N1 C4 126.8(3) .
N2 B1 N1 C4 9.4(4) .
F1 B1 N2 C9 -62.9(4) .
F2 B1 N2 C9 60.0(4) .
N1 B1 N2 C9 177.3(3) .
F1 B1 N2 C6 104.2(3) .
F2 B1 N2 C6 -132.9(3) .
N1 B1 N2 C6 -15.6(4) .
C4 N1 C1 C2 -1.3(3) .
B1 N1 C1 C2 176.6(3) .
C4 N1 C1 Br1 178.2(2) .
B1 N1 C1 Br1 -3.9(4) .
N1 C1 C2 C3 0.6(4) .
Br1 C1 C2 C3 -178.8(2) .
N1 C1 C2 Br2 -177.0(2) .
Br1 C1 C2 Br2 3.5(4) .
Br4 Br2 C2 C3 28.6(3) 1_565
Br4 Br2 C2 C1 -154.2(3) 1_565
C1 C2 C3 C4 0.3(3) .
Br2 C2 C3 C4 177.8(2) .
C1 N1 C4 C3 1.4(3) .
B1 N1 C4 C3 -176.5(3) .
C1 N1 C4 C5 176.7(3) .
B1 N1 C4 C5 -1.2(4) .
C2 C3 C4 N1 -1.1(3) .
C2 C3 C4 C5 -175.7(3) .
N1 C4 C5 C6 -3.3(4) .
C3 C4 C5 C6 170.8(3) .
N1 C4 C5 C10 177.9(3) .
C3 C4 C5 C10 -8.0(5) .
C9 N2 C6 C5 -177.1(3) .
B1 N2 C6 C5 13.7(4) .
C9 N2 C6 C7 0.4(3) .
B1 N2 C6 C7 -168.8(3) .
C4 C5 C6 N2 -2.7(4) .
C10 C5 C6 N2 176.1(3) .
C4 C5 C6 C7 -179.5(3) .
C10 C5 C6 C7 -0.8(5) .
N2 C6 C7 C8 -0.8(3) .
C5 C6 C7 C8 176.3(3) .
C6 C7 C8 C9 1.0(3) .
C6 C7 C8 Br3 -176.6(2) .
C6 N2 C9 C8 0.2(3) .
B1 N2 C9 C8 169.3(3) .
C6 N2 C9 Br4 -179.4(2) .
B1 N2 C9 Br4 -10.3(4) .
C7 C8 C9 N2 -0.8(4) .
Br3 C8 C9 N2 176.9(2) .
C7 C8 C9 Br4 178.8(2) .
Br3 C8 C9 Br4 -3.5(4) .
C6 C5 C10 C11 -49.4(4) .
C4 C5 C10 C11 129.4(3) .
C6 C5 C10 C15 129.3(3) .
C4 C5 C10 C15 -51.9(4) .
C15 C10 C11 C12 0.0(4) .
C5 C10 C11 C12 178.7(3) .
C10 C11 C12 C13 -0.6(5) .
C16 O1 C13 C14 -3.8(5) .
C16 O1 C13 C12 177.5(3) .
C11 C12 C13 O1 179.2(3) .
C11 C12 C13 C14 0.5(5) .
O1 C13 C14 C15 -178.3(3) .
C12 C13 C14 C15 0.3(5) .
C13 C14 C15 C10 -0.9(4) .
C11 C10 C15 C14 0.7(4) .
C5 C10 C15 C14 -177.9(3) .
