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#$Revision: 301836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/65/4306531.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_4306531
loop_
_publ_author_name
'Shin Hei Choi'
'Kibong Kim'
'June Jeon'
'Bhupal Meka'
'Daniela Bucella'
'Keliang Pang'
'Snehadrinarayan Khatua'
'Junseong Lee'
'David G. Churchill'
_publ_section_title
;
Optical Effects of S-Oxidation and Mn+ Binding in meso-Thienyl Dipyrrin
Systems and of Stepwise Bromination of
4,4-Difluoro-8-(2,5-dibromo-3-thienyl)-4-bora-3a,4a-diaza-s-indacene
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11071
_journal_page_last               11083
_journal_paper_doi               10.1021/ic801354y
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C13 H9 B F2 N2 S'
_chemical_formula_weight         274.09
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 111.6450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7431(10)
_cell_length_b                   10.1739(7)
_cell_length_c                   7.7513(5)
_cell_measurement_temperature    243(2)
_cell_volume                     1227.27(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      243(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4255
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9603
_exptl_absorpt_correction_T_min  0.9227
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(15)
_refine_ls_extinction_coef       0.0013(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1888
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0379
_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)+(0.0717P)²+0.5783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                1681
_reflns_number_total             1888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801354y_si_002.cif
_cod_data_source_block           shbfs10
_cod_database_code               4306531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.38760(17) 1.2928(2) 0.7443(4) 0.0406(6) Uani 1 1 d . . .
N2 N 0.28980(16) 1.1275(2) 0.5430(3) 0.0384(6) Uani 1 1 d . . .
B B 0.3009(2) 1.2766(4) 0.5796(6) 0.0480(9) Uani 1 1 d . . .
F1 F 0.23550(16) 1.3259(2) 0.6272(4) 0.0758(7) Uani 1 1 d . . .
F2 F 0.30459(18) 1.3391(2) 0.4237(3) 0.0756(8) Uani 1 1 d . . .
C1 C 0.4180(3) 1.4029(3) 0.8408(6) 0.0582(9) Uani 1 1 d . . .
H1A H 0.3900 1.4847 0.8172 0.070 Uiso 1 1 calc R . .
C2 C 0.4965(3) 1.3789(3) 0.9797(6) 0.0605(10) Uani 1 1 d . . .
H2A H 0.5303 1.4409 1.0656 0.073 Uiso 1 1 calc R . .
C3 C 0.5166(2) 1.2481(3) 0.9708(5) 0.0432(7) Uani 1 1 d . . .
H3A H 0.5661 1.2041 1.0490 0.052 Uiso 1 1 calc R . .
C4 C 0.44825(19) 1.1939(3) 0.8212(4) 0.0333(6) Uani 1 1 d . . .
C5 C 0.43065(18) 1.0626(3) 0.7589(4) 0.0302(5) Uani 1 1 d . . .
C6 C 0.35152(19) 1.0305(3) 0.6211(4) 0.0338(6) Uani 1 1 d . . .
C7 C 0.3169(2) 0.9097(3) 0.5342(4) 0.0388(7) Uani 1 1 d . . .
H7A H 0.3447 0.8277 0.5584 0.047 Uiso 1 1 calc R . .
C8 C 0.2353(2) 0.9340(4) 0.4081(4) 0.0468(8) Uani 1 1 d . . .
H8A H 0.1967 0.8723 0.3312 0.056 Uiso 1 1 calc R . .
C9 C 0.2215(2) 1.0691(4) 0.4173(4) 0.0471(8) Uani 1 1 d . . .
H9A H 0.1708 1.1130 0.3447 0.057 Uiso 1 1 calc R . .
S S 0.56773(9) 0.74728(9) 0.99109(14) 0.0603(3) Uani 1 1 d . . .
C11 C 0.49606(18) 0.9614(3) 0.8416(4) 0.0329(6) Uani 1 1 d . . .
C12 C 0.5854(2) 0.9786(3) 0.8817(4) 0.0428(7) Uani 1 1 d . . .
H12A H 0.6088 1.0563 0.8543 0.051 Uiso 1 1 calc R . .
C13 C 0.6363(2) 0.8673(3) 0.9671(4) 0.0438(7) Uani 1 1 d . . .
H13A H 0.6963 0.8603 1.0039 0.053 Uiso 1 1 calc R . .
C14 C 0.4785(2) 0.8386(3) 0.8932(4) 0.0399(7) Uani 1 1 d . . .
H14A H 0.4229 0.8090 0.8756 0.048 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'
S S 0.1246 0.1234 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 107.3(3) . . ?
C1 N1 B 126.7(3) . . ?
C4 N1 B 126.0(3) . . ?
C9 N2 C6 107.4(3) . . ?
C9 N2 B 125.7(3) . . ?
C6 N2 B 126.6(3) . . ?
F1 B F2 111.3(3) . . ?
F1 B N2 110.8(3) . . ?
F2 B N2 109.4(3) . . ?
F1 B N1 109.7(3) . . ?
F2 B N1 109.9(3) . . ?
N2 B N1 105.6(2) . . ?
N1 C1 C2 110.2(3) . . ?
C1 C2 C3 108.2(3) . . ?
C2 C3 C4 106.2(3) . . ?
N1 C4 C3 108.2(3) . . ?
N1 C4 C5 120.5(3) . . ?
C3 C4 C5 131.0(3) . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 C11 120.9(2) . . ?
C4 C5 C11 119.1(3) . . ?
N2 C6 C5 120.5(3) . . ?
N2 C6 C7 107.4(3) . . ?
C5 C6 C7 132.1(3) . . ?
C8 C7 C6 107.8(3) . . ?
C7 C8 C9 106.2(3) . . ?
N2 C9 C8 111.1(3) . . ?
C14 S C13 94.33(16) . . ?
C14 C11 C12 111.6(3) . . ?
C14 C11 C5 124.0(3) . . ?
C12 C11 C5 124.4(3) . . ?
C11 C12 C13 113.8(3) . . ?
C12 C13 S 107.7(3) . . ?
C11 C14 S 112.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.339(5) . ?
N1 C4 1.397(4) . ?
N1 B 1.548(5) . ?
N2 C9 1.337(4) . ?
N2 C6 1.395(4) . ?
N2 B 1.542(5) . ?
B F1 1.373(5) . ?
B F2 1.387(5) . ?
C1 C2 1.379(6) . ?
C2 C3 1.381(5) . ?
C3 C4 1.407(4) . ?
C4 C5 1.414(4) . ?
C5 C6 1.400(4) . ?
C5 C11 1.467(4) . ?
C6 C7 1.419(4) . ?
C7 C8 1.377(4) . ?
C8 C9 1.400(5) . ?
S C14 1.684(3) . ?
S C13 1.732(4) . ?
C11 C14 1.376(4) . ?
C11 C12 1.422(4) . ?
C12 C13 1.425(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139128558
