#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:28:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180183 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/79/7107997.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_7107997
loop_
_publ_author_name
'Atul P. Singh'
'Kang Mun Lee'
'Dhiraj P. Murale'
'Taehong Jun'
'Hyunjeong Liew'
'Yoo-Hun Suh'
'David G. Churchill'
_publ_section_title
;
 Novel sulphur-rich BODIPY systems that enable stepwise fluorescent O-atom
 turn-on and H2O2 neuronal system probing
;
_journal_name_full               Chem.Commun.
_journal_page_first              7298
_journal_paper_doi               10.1039/c2cc33076h
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         C12H13B1F2N2
_chemical_formula_sum            'C12 H13 B F2 N2'
_chemical_formula_weight         234.05
_chemical_name_systematic
;
?
;
_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_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                 94.75(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.350(3)
_cell_length_b                   13.032(7)
_cell_length_c                   14.253(7)
_cell_measurement_reflns_used    4133
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.15
_cell_measurement_theta_min      2.12
_cell_volume                     1175.4(10)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0857
_diffrn_reflns_av_sigmaI/netI    0.1658
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16333
_diffrn_reflns_theta_full        32.15
_diffrn_reflns_theta_max         32.15
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Darkred
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.2216
_refine_ls_R_factor_gt           0.0992
_refine_ls_shift/su_max          0.075
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0692P)²+0.2425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2524
_reflns_number_gt                1720
_reflns_number_total             4133
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc33076h.txt
_cod_data_source_block           nchu82-1
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7107997
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_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
B B 0.2057(5) 0.2339(3) 0.4822(2) 0.0527(8) Uani 1 1 d .
F1 F 0.1192(3) 0.30817(15) 0.53913(12) 0.0802(6) Uani 1 1 d .
F2 F 0.3213(3) 0.16538(16) 0.53975(13) 0.0843(7) Uani 1 1 d .
N1 N 0.3474(4) 0.28589(16) 0.41335(15) 0.0474(6) Uani 1 1 d .
N2 N 0.0251(3) 0.17820(16) 0.42308(15) 0.0467(6) Uani 1 1 d .
C1 C 0.5228(5) 0.3437(2) 0.4337(2) 0.0565(8) Uani 1 1 d .
H1 H 0.5778 0.3594 0.4945 0.068 Uiso 1 1 calc R
C2 C 0.6105(4) 0.37696(19) 0.3528(2) 0.0513(7) Uani 1 1 d .
C3 C 0.4817(5) 0.3365(2) 0.2785(2) 0.0522(7) Uani 1 1 d .
H3 H 0.4998 0.3454 0.2150 0.063 Uiso 1 1 calc R
C4 C 0.3191(4) 0.27972(19) 0.31542(17) 0.0456(6) Uani 1 1 d .
C5 C 0.1482(4) 0.22561(19) 0.27307(17) 0.0459(7) Uani 1 1 d .
H5 H 0.1310 0.2226 0.2077 0.055 Uiso 1 1 calc R
C6 C 0.0036(4) 0.17632(18) 0.32398(17) 0.0438(6) Uani 1 1 d .
C7 C -0.1833(4) 0.1200(2) 0.2947(2) 0.0498(7) Uani 1 1 d .
C8 C -0.2681(5) 0.0882(2) 0.3757(2) 0.0568(8) Uani 1 1 d .
H8 H -0.3900 0.0492 0.3785 0.068 Uiso 1 1 calc R
C9 C -0.1392(4) 0.1248(2) 0.45317(19) 0.0520(7) Uani 1 1 d .
C10 C 0.8024(5) 0.4439(3) 0.3494(3) 0.0740(9) Uani 1 1 d .
H21A H 0.7629 0.5144 0.3564 0.111 Uiso 1 1 calc R
H21B H 0.8614 0.4348 0.2901 0.111 Uiso 1 1 calc R
H21C H 0.9054 0.4253 0.3996 0.111 Uiso 1 1 calc R
C11 C -0.2663(5) 0.1023(2) 0.1946(2) 0.0655(9) Uani 1 1 d .
H10A H -0.2838 0.0300 0.1836 0.098 Uiso 1 1 calc R
H10B H -0.1681 0.1293 0.1532 0.098 Uiso 1 1 calc R
H10C H -0.4001 0.1361 0.1827 0.098 Uiso 1 1 calc R
C12 C -0.1683(5) 0.1092(3) 0.5549(2) 0.0674(9) Uani 1 1 d .
H13A H -0.0329 0.1002 0.5892 0.101 Uiso 1 1 calc R
H13B H -0.2532 0.0492 0.5623 0.101 Uiso 1 1 calc R
H13C H -0.2375 0.1680 0.5788 0.101 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'
F F 0.0171 0.0103 '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
F2 B F1 108.5(2)
F2 B N1 110.6(3)
F1 B N1 110.0(2)
F2 B N2 110.7(3)
F1 B N2 109.3(2)
N1 B N2 107.8(2)
C1 N1 C4 106.4(2)
C1 N1 B 128.3(2)
C4 N1 B 125.3(2)
C9 N2 C6 107.2(2)
C9 N2 B 128.7(2)
C6 N2 B 124.1(2)
N1 C1 C2 112.0(2)
C3 C2 C1 105.2(2)
C3 C2 C10 128.7(3)
C1 C2 C10 126.1(3)
C2 C3 C4 108.6(2)
C5 C4 N1 119.7(2)
C5 C4 C3 132.5(2)
N1 C4 C3 107.8(2)
C6 C5 C4 122.6(2)
C5 C6 N2 120.5(2)
C5 C6 C7 131.3(2)
N2 C6 C7 108.1(2)
C8 C7 C6 106.4(2)
C8 C7 C11 128.4(3)
C6 C7 C11 125.2(3)
C7 C8 C9 108.3(3)
N2 C9 C8 109.9(2)
N2 C9 C12 122.7(3)
C8 C9 C12 127.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B F2 1.382(4)
B F1 1.404(4)
B N1 1.542(4)
B N2 1.547(4)
N1 C1 1.356(4)
N1 C4 1.395(3)
N2 C9 1.353(3)
N2 C6 1.408(3)
C1 C2 1.390(4)
C2 C3 1.388(4)
C2 C10 1.502(4)
C3 C4 1.407(4)
C4 C5 1.389(4)
C5 C6 1.376(4)
C6 C7 1.428(4)
C7 C8 1.377(4)
C7 C11 1.497(4)
C8 C9 1.403(4)
C9 C12 1.491(4)
