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#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/65/4306533.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_4306533
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            'C13.5 H B Br8 Cl F2 N2 S'
_chemical_formula_weight         946.76
_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                111.075(14)
_cell_angle_beta                 99.542(14)
_cell_angle_gamma                104.441(10)
_cell_formula_units_Z            2
_cell_length_a                   8.844(5)
_cell_length_b                   11.556(7)
_cell_length_c                   12.998(11)
_cell_measurement_temperature    296(2)
_cell_volume                     1151.4(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.886
_diffrn_measured_fraction_theta_max 0.886
_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  0.1208
_diffrn_reflns_av_sigmaI/netI    0.2502
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7674
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    14.160
_exptl_crystal_density_diffrn    2.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_refine_diff_density_max         1.211
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.237
_refine_ls_extinction_coef       0.0066(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.2620
_refine_ls_R_factor_gt           0.0921
_refine_ls_shift/su_max          0.241
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0720P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2389
_reflns_number_gt                1500
_reflns_number_total             4640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801354y_si_004.cif
_cod_data_source_block           dave18
_cod_original_cell_volume        1151.3(14)
_cod_original_formula_sum        'C13.50 H B Br8 Cl F2 N2 S'
_cod_database_code               4306533
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
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 1.656(2) 0.403(3) 0.4084(17) 0.054(7) Uani 1 1 d . . .
F1 F 1.7032(10) 0.4441(11) 0.5257(7) 0.062(3) Uani 1 1 d . . .
F2 F 1.7663(11) 0.3532(10) 0.3605(8) 0.056(3) Uani 1 1 d . . .
N1 N 1.6267(15) 0.5092(16) 0.3766(11) 0.038(4) Uani 1 1 d . . .
N2 N 1.4867(16) 0.2905(16) 0.3599(12) 0.044(4) Uani 1 1 d . . .
C1 C 1.739(2) 0.626(2) 0.4081(14) 0.047(5) Uani 1 1 d . . .
C2 C 1.683(2) 0.700(2) 0.3568(16) 0.055(6) Uani 1 1 d . . .
C3 C 1.520(2) 0.622(2) 0.2905(13) 0.041(5) Uani 1 1 d . . .
C4 C 1.4908(19) 0.503(2) 0.2987(13) 0.041(5) Uani 1 1 d . . .
C5 C 1.3507(17) 0.387(2) 0.2570(14) 0.039(5) Uani 1 1 d . . .
C6 C 1.351(2) 0.286(2) 0.2895(13) 0.045(5) Uani 1 1 d . . .
C7 C 1.221(2) 0.158(2) 0.2529(15) 0.049(5) Uani 1 1 d . . .
C8 C 1.289(2) 0.097(2) 0.3105(17) 0.059(6) Uani 1 1 d . . .
C9 C 1.451(2) 0.180(3) 0.3729(14) 0.056(6) Uani 1 1 d . . .
C10 C 1.2026(17) 0.3822(18) 0.1797(13) 0.041(5) Uani 1 1 d . . .
C11 C 1.1742(19) 0.3372(19) 0.0688(14) 0.047(5) Uani 1 1 d . . .
C12 C 0.9571(18) 0.410(2) 0.1269(13) 0.051(5) Uani 1 1 d . . .
C13 C 1.0792(19) 0.4278(19) 0.2164(14) 0.053(6) Uani 1 1 d . . .
H13 H 1.0807 0.4662 0.2931 0.064 Uiso 1 1 calc R . .
S1 S 0.9963(5) 0.3431(6) -0.0001(4) 0.0572(15) Uani 1 1 d . . .
Br1 Br 1.9464(3) 0.6798(3) 0.4973(2) 0.0941(10) Uani 1 1 d . . .
Br2 Br 1.7894(3) 0.8664(2) 0.3722(2) 0.0823(8) Uani 1 1 d . . .
Br3 Br 1.3895(3) 0.6754(3) 0.2056(2) 0.0850(9) Uani 1 1 d . . .
Br4 Br 1.0177(3) 0.1000(3) 0.1671(3) 0.1265(12) Uani 1 1 d . . .
Br5 Br 1.1843(3) -0.0648(3) 0.3033(2) 0.0888(9) Uani 1 1 d . . .
Br6 Br 1.5907(3) 0.1366(3) 0.4591(3) 0.1146(11) Uani 1 1 d . . .
Br7 Br 1.3127(2) 0.2793(3) -0.01908(17) 0.0785(9) Uani 1 1 d . . .
Br8 Br 0.7679(2) 0.4481(3) 0.13016(18) 0.0805(9) Uani 1 1 d . . .
C20 C 0.521(5) 0.045(4) -0.113(3) 0.060(11) Uiso 0.50 1 d P . .
Cl1 Cl 0.650(4) 0.062(3) -0.021(3) 0.232(11) Uiso 0.50 1 d P . .
Cl2 Cl 0.395(7) -0.074(6) -0.135(5) 0.41(3) Uiso 0.50 1 d P . .
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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
F1 B1 F2 109.9(17) . . ?
F1 B1 N1 111.9(18) . . ?
F2 B1 N1 113.2(17) . . ?
F1 B1 N2 107.4(15) . . ?
F2 B1 N2 108.5(17) . . ?
N1 B1 N2 105.5(16) . . ?
C1 N1 C4 106.4(15) . . ?
C1 N1 B1 124.2(14) . . ?
C4 N1 B1 128.9(16) . . ?
C9 N2 C6 107.1(15) . . ?
C9 N2 B1 127.4(16) . . ?
C6 N2 B1 125.4(18) . . ?
N1 C1 C2 111.9(15) . . ?
N1 C1 Br1 125.2(14) . . ?
C2 C1 Br1 122.6(17) . . ?
C1 C2 C3 105.4(18) . . ?
C1 C2 Br2 129.0(15) . . ?
C3 C2 Br2 125.5(17) . . ?
C4 C3 C2 106.7(16) . . ?
C4 C3 Br3 129.8(13) . . ?
C2 C3 Br3 123.3(17) . . ?
C3 C4 N1 109.3(16) . . ?
C3 C4 C5 134.4(16) . . ?
N1 C4 C5 115.8(18) . . ?
C6 C5 C4 121.8(16) . . ?
C6 C5 C10 121.6(16) . . ?
C4 C5 C10 116.5(17) . . ?
N2 C6 C5 121.3(17) . . ?
N2 C6 C7 109.8(18) . . ?
C5 C6 C7 128.8(16) . . ?
C8 C7 C6 103.6(17) . . ?
C8 C7 Br4 126.0(16) . . ?
C6 C7 Br4 130.1(15) . . ?
C7 C8 C9 107.5(18) . . ?
C7 C8 Br5 124.7(16) . . ?
C9 C8 Br5 127.8(18) . . ?
N2 C9 C8 112.0(17) . . ?
N2 C9 Br6 124.9(14) . . ?
C8 C9 Br6 123.1(19) . . ?
C11 C10 C13 111.7(14) . . ?
C11 C10 C5 123.2(14) . . ?
C13 C10 C5 125.1(14) . . ?
C10 C11 S1 114.1(12) . . ?
C10 C11 Br7 127.3(12) . . ?
S1 C11 Br7 118.5(9) . . ?
C13 C12 S1 111.5(11) . . ?
C13 C12 Br8 128.8(12) . . ?
S1 C12 Br8 119.7(8) . . ?
C12 C13 C10 112.4(14) . . ?
C12 S1 C11 90.3(8) . . ?
Cl2 C20 Cl1 105(4) . . ?
C20 Cl1 Cl2 119(3) . 2_655 ?
C20 Cl1 Cl2 37(2) . . ?
Cl2 Cl1 Cl2 96(2) 2_655 . ?
C20 Cl2 Cl1 108(4) . 2_655 ?
C20 Cl2 Cl1 37(2) . . ?
Cl1 Cl2 Cl1 84(2) 2_655 . ?
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
B1 F1 1.38(2) . ?
B1 F2 1.38(2) . ?
B1 N1 1.49(3) . ?
B1 N2 1.57(2) . ?
N1 C1 1.33(2) . ?
N1 C4 1.408(18) . ?
N2 C9 1.31(2) . ?
N2 C6 1.36(2) . ?
C1 C2 1.39(2) . ?
C1 Br1 1.818(17) . ?
C2 C3 1.42(2) . ?
C2 Br2 1.83(2) . ?
C3 C4 1.38(2) . ?
C3 Br3 1.828(18) . ?
C4 C5 1.44(2) . ?
C5 C6 1.38(2) . ?
C5 C10 1.49(2) . ?
C6 C7 1.48(2) . ?
C7 C8 1.37(2) . ?
C7 Br4 1.765(18) . ?
C8 C9 1.42(2) . ?
C8 Br5 1.83(2) . ?
C9 Br6 1.816(19) . ?
C10 C11 1.30(2) . ?
C10 C13 1.41(2) . ?
C11 S1 1.706(16) . ?
C11 Br7 1.890(16) . ?
C12 C13 1.36(2) . ?
C12 S1 1.687(16) . ?
C12 Br8 1.838(15) . ?
C20 Cl2 1.43(6) . ?
C20 Cl1 1.43(4) . ?
Cl1 Cl2 2.09(7) 2_655 ?
Cl1 Cl2 2.28(6) . ?
Cl2 Cl1 2.09(7) 2_655 ?
