#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:49:17 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178446 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/67/4026781.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_4026781
loop_
_publ_author_name
'Lijuan Jiao'
'Weidong Pang'
'Jinyuan Zhou'
'Yun Wei'
'Xiaolong Mu'
'Guifeng Bai'
'Erhong Hao'
_publ_section_title
;
 Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9988
_journal_page_last               9996
_journal_paper_doi               10.1021/jo201754m
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C16 H11 B Br2 F2 N2 O'
_chemical_formula_weight         455.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 90.743(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.346(4)
_cell_length_b                   10.948(6)
_cell_length_c                   20.674(12)
_cell_measurement_reflns_used    2468
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.77
_cell_measurement_theta_min      2.71
_cell_volume                     1662.5(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1463
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13649
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    4.901
_exptl_absorpt_correction_T_max  0.5470
_exptl_absorpt_correction_T_min  0.4259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Semi-empirical from equivalents'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.104
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         13649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0801
_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)+(0.1032P)²+2.7578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2510
_reflns_number_gt                6540
_reflns_number_total             13649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201754m_si_005.cif
_cod_data_source_block           BODIPY3b
_cod_original_cell_volume        1662.6(16)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4026781
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C -0.0449(10) 0.3496(6) 0.1002(4) 0.0507(18) Uani 1 1 d .
H1 H -0.0777 0.3386 0.0570 0.061 Uiso 1 1 calc R
C2 C -0.1474(9) 0.3128(5) 0.1539(3) 0.0478(17) Uani 1 1 d .
C3 C -0.0535(9) 0.3496(5) 0.2096(3) 0.0446(17) Uani 1 1 d .
H3 H -0.0911 0.3384 0.2520 0.054 Uiso 1 1 calc R
C4 C 0.1104(9) 0.4074(5) 0.1899(3) 0.0405(15) Uani 1 1 d .
C5 C 0.2530(8) 0.4601(5) 0.2246(3) 0.0354(14) Uani 1 1 d .
C6 C 0.3949(9) 0.5165(5) 0.1933(3) 0.0373(14) Uani 1 1 d .
C7 C 0.5593(9) 0.5702(5) 0.2162(3) 0.0422(16) Uani 1 1 d .
H7 H 0.5975 0.5773 0.2591 0.051 Uiso 1 1 calc R
C8 C 0.6502(9) 0.6092(5) 0.1631(3) 0.0454(16) Uani 1 1 d .
C9 C 0.5508(10) 0.5764(6) 0.1087(3) 0.0506(19) Uani 1 1 d .
H9 H 0.5861 0.5912 0.0664 0.061 Uiso 1 1 calc R
C10 C 0.2515(8) 0.4602(5) 0.2971(3) 0.0377(15) Uani 1 1 d .
C11 C 0.2209(8) 0.3538(5) 0.3322(3) 0.0396(15) Uani 1 1 d .
H11 H 0.1990 0.2807 0.3105 0.048 Uiso 1 1 calc R
C12 C 0.2228(9) 0.3562(6) 0.3986(3) 0.0482(17) Uani 1 1 d .
H12 H 0.2106 0.2838 0.4216 0.058 Uiso 1 1 calc R
C13 C 0.2427(9) 0.4655(6) 0.4315(3) 0.0439(16) Uani 1 1 d .
C14 C 0.2674(9) 0.5720(5) 0.3977(3) 0.0471(17) Uani 1 1 d .
H14 H 0.2805 0.6458 0.4196 0.056 Uiso 1 1 calc R
C15 C 0.2729(8) 0.5692(5) 0.3308(3) 0.0420(16) Uani 1 1 d .
H15 H 0.2913 0.6413 0.3081 0.050 Uiso 1 1 calc R
C16 C 0.2521(12) 0.5694(7) 0.5344(4) 0.081(3) Uani 1 1 d .
H16A H 0.3724 0.6029 0.5312 0.121 Uiso 1 1 calc R
H16B H 0.2254 0.5536 0.5789 0.121 Uiso 1 1 calc R
H16C H 0.1653 0.6267 0.5170 0.121 Uiso 1 1 calc R
B1 B 0.2536(13) 0.4660(8) 0.0787(4) 0.055(2) Uani 1 1 d .
O1 O 0.2416(7) 0.4563(4) 0.4980(2) 0.0649(14) Uani 1 1 d .
F1 F 0.1766(7) 0.5575(4) 0.04146(19) 0.0787(13) Uani 1 1 d .
F2 F 0.3308(7) 0.3773(4) 0.03964(18) 0.0785(13) Uani 1 1 d .
Br1 Br -0.36608(11) 0.22660(7) 0.14791(4) 0.0665(3) Uani 1 1 d .
Br2 Br 0.87234(10) 0.69492(7) 0.16085(4) 0.0646(3) Uani 1 1 d .
N1 N 0.1102(8) 0.4043(4) 0.1223(2) 0.0427(13) Uani 1 1 d .
N2 N 0.3944(8) 0.5193(4) 0.1256(3) 0.0436(13) Uani 1 1 d .
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'
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'
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
N1 C1 C2 108.4(6)
N1 C1 H1 125.8
C2 C1 H1 125.8
C3 C2 C1 107.7(6)
C3 C2 Br1 128.1(6)
C1 C2 Br1 124.2(5)
C2 C3 C4 107.7(6)
C2 C3 H3 126.2
C4 C3 H3 126.2
C5 C4 N1 121.2(6)
C5 C4 C3 132.3(6)
N1 C4 C3 106.6(6)
C6 C5 C4 120.9(6)
C6 C5 C10 118.9(6)
C4 C5 C10 120.1(5)
C5 C6 N2 119.1(6)
C5 C6 C7 132.3(6)
N2 C6 C7 108.5(5)
C8 C7 C6 106.5(6)
C8 C7 H7 126.8
C6 C7 H7 126.8
C7 C8 C9 108.4(6)
C7 C8 Br2 127.6(5)
C9 C8 Br2 124.0(5)
N2 C9 C8 110.5(6)
N2 C9 H9 124.7
C8 C9 H9 124.7
C15 C10 C11 118.3(6)
C15 C10 C5 120.0(5)
C11 C10 C5 121.6(5)
C12 C11 C10 120.4(6)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 120.6(6)
C11 C12 H12 119.7
C13 C12 H12 119.7
C14 C13 O1 124.9(6)
C14 C13 C12 119.8(6)
O1 C13 C12 115.2(6)
C13 C14 C15 119.7(6)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C10 121.1(6)
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
F1 B1 F2 110.5(6)
F1 B1 N2 110.3(6)
F2 B1 N2 111.0(7)
F1 B1 N1 111.4(7)
F2 B1 N1 108.6(6)
N2 B1 N1 104.9(6)
C13 O1 C16 116.9(5)
C1 N1 C4 109.7(6)
C1 N1 B1 124.6(6)
C4 N1 B1 125.4(6)
C9 N2 C6 106.0(5)
C9 N2 B1 125.5(6)
C6 N2 B1 128.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.361(8)
C1 C2 1.408(9)
C1 H1 0.9300
C2 C3 1.395(8)
C2 Br1 1.866(7)
C3 C4 1.424(9)
C3 H3 0.9300
C4 C5 1.387(8)
C4 N1 1.398(7)
C5 C6 1.381(8)
C5 C10 1.499(8)
C6 N2 1.398(8)
C6 C7 1.419(8)
C7 C8 1.362(8)
C7 H7 0.9300
C8 C9 1.379(9)
C8 Br2 1.883(7)
C9 N2 1.358(8)
C9 H9 0.9300
C10 C15 1.390(8)
C10 C11 1.392(8)
C11 C12 1.372(8)
C11 H11 0.9300
C12 C13 1.384(9)
C12 H12 0.9300
C13 C14 1.373(9)
C13 O1 1.379(7)
C14 C15 1.384(8)
C14 H14 0.9300
C15 H15 0.9300
C16 O1 1.450(8)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
B1 F1 1.381(9)
B1 F2 1.389(9)
B1 N2 1.525(10)
B1 N1 1.550(10)
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
N1 C1 C2 C3 1.8(7)
N1 C1 C2 Br1 -176.8(4)
C1 C2 C3 C4 -1.2(7)
Br1 C2 C3 C4 177.3(4)
C2 C3 C4 C5 -179.7(6)
C2 C3 C4 N1 0.3(6)
N1 C4 C5 C6 3.3(9)
C3 C4 C5 C6 -176.7(6)
N1 C4 C5 C10 -178.9(5)
C3 C4 C5 C10 1.2(10)
C4 C5 C6 N2 -0.5(8)
C10 C5 C6 N2 -178.4(5)
C4 C5 C6 C7 -175.8(6)
C10 C5 C6 C7 6.3(10)
C5 C6 C7 C8 178.5(6)
N2 C6 C7 C8 2.8(6)
C6 C7 C8 C9 -2.7(7)
C6 C7 C8 Br2 176.9(4)
C7 C8 C9 N2 1.6(7)
Br2 C8 C9 N2 -178.0(4)
C6 C5 C10 C15 51.4(8)
C4 C5 C10 C15 -126.5(6)
C6 C5 C10 C11 -131.5(6)
C4 C5 C10 C11 50.6(8)
C15 C10 C11 C12 -3.8(9)
C5 C10 C11 C12 179.1(6)
C10 C11 C12 C13 4.4(10)
C11 C12 C13 C14 -2.4(10)
C11 C12 C13 O1 179.7(6)
O1 C13 C14 C15 177.5(6)
C12 C13 C14 C15 -0.2(10)
C13 C14 C15 C10 0.8(10)
C11 C10 C15 C14 1.2(9)
C5 C10 C15 C14 178.4(6)
C14 C13 O1 C16 5.5(10)
C12 C13 O1 C16 -176.7(7)
C2 C1 N1 C4 -1.6(7)
C2 C1 N1 B1 -175.4(6)
C5 C4 N1 C1 -179.1(5)
C3 C4 N1 C1 0.8(6)
C5 C4 N1 B1 -5.4(9)
C3 C4 N1 B1 174.6(6)
F1 B1 N1 C1 57.6(9)
F2 B1 N1 C1 -64.4(9)
N2 B1 N1 C1 176.9(5)
F1 B1 N1 C4 -115.3(7)
F2 B1 N1 C4 122.8(6)
N2 B1 N1 C4 4.1(9)
C8 C9 N2 C6 0.2(7)
C8 C9 N2 B1 -177.7(6)
C5 C6 N2 C9 -178.2(5)
C7 C6 N2 C9 -1.9(6)
C5 C6 N2 B1 -0.3(9)
C7 C6 N2 B1 176.0(6)
F1 B1 N2 C9 -63.7(9)
F2 B1 N2 C9 59.1(8)
N1 B1 N2 C9 176.2(5)
F1 B1 N2 C6 118.8(7)
F2 B1 N2 C6 -118.4(7)
N1 B1 N2 C6 -1.3(9)
