#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:28:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180395 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/64/7206460.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_7206460
loop_
_publ_author_name
'Welch, Gregory C.'
'Perez, Louis A.'
'Hoven, Corey V.'
'Zhang, Yuan'
'Dang, Xuan-Dung'
'Sharenko, Alexander'
'Toney, Michael F.'
'Kramer, Edward J.'
'Nguyen, Thuc-Quyen'
'Bazan, Guillermo C.'
_publ_section_title
;
 A modular molecular framework for utility in small-molecule
 solution-processed organic photovoltaic devices
;
_journal_issue                   34
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              12700
_journal_paper_doi               10.1039/c1jm11963j
_journal_volume                  21
_journal_year                    2011
_chemical_formula_sum            'C9 H4 Br N3 S2'
_chemical_formula_weight         298.18
_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                 92.743(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6471(8)
_cell_length_b                   20.920(3)
_cell_length_c                   10.6360(18)
_cell_measurement_temperature    293(2)
_cell_volume                     1032.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'CCD Area detector'
_diffrn_measurement_method       'Omega scan'
_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  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5469
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    4.349
_exptl_absorpt_correction_T_max  0.389
_exptl_absorpt_correction_T_min  0.207
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi scan'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.918
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0412
_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)+(0.0498P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                1324
_reflns_number_total             1998
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1jm11963j.txt
_cod_data_source_block           greg
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7206460
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
Br Br 0.33541(11) 0.39750(2) 0.78754(5) 0.0582(2) Uani 1 1 d .
C1 C 0.5072(9) 0.4786(2) 0.7864(4) 0.0387(10) Uani 1 1 d .
C2 C 0.7139(10) 0.4968(2) 0.8748(4) 0.0448(12) Uani 1 1 d .
H2 H 0.7679 0.4677 0.9376 0.054 Uiso 1 1 calc R
C3 C 0.7786(9) 0.5994(2) 0.7904(4) 0.0379(10) Uani 1 1 d .
C4 C 0.5663(9) 0.5842(2) 0.6923(4) 0.0355(10) Uani 1 1 d .
C5 C 0.4273(9) 0.5239(2) 0.6919(3) 0.0367(10) Uani 1 1 d .
C6 C 0.9303(9) 0.6603(2) 0.7992(4) 0.0421(11) Uani 1 1 d .
C7 C 1.2518(13) 0.7451(3) 0.8772(5) 0.0699(17) Uani 1 1 d .
H7 H 1.3827 0.7717 0.9204 0.084 Uiso 1 1 calc R
C8 C 1.1167(12) 0.7611(3) 0.7660(5) 0.0664(15) Uani 1 1 d .
H8 H 1.1502 0.7997 0.7257 0.080 Uiso 1 1 calc R
C9 C 0.9185(9) 0.7144(2) 0.7150(4) 0.0440(11) Uani 1 1 d .
H9 H 0.8036 0.7183 0.6414 0.053 Uiso 1 1 calc R
N1 N 0.8459(8) 0.55484(17) 0.8768(3) 0.0424(9) Uani 1 1 d .
N2 N 0.4730(8) 0.62220(18) 0.5954(3) 0.0435(10) Uani 1 1 d .
N3 N 0.2258(8) 0.51594(18) 0.5970(3) 0.0435(10) Uani 1 1 d .
S1 S 0.2289(3) 0.58159(6) 0.51711(10) 0.0482(3) Uani 1 1 d .
S2 S 1.1591(3) 0.67182(7) 0.92983(13) 0.0711(5) 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C5 116.9(4)
C2 C1 Br 122.3(3)
C5 C1 Br 120.8(3)
N1 C2 C1 124.2(4)
N1 C2 H2 117.9
C1 C2 H2 117.9
N1 C3 C4 118.3(4)
N1 C3 C6 118.0(3)
C4 C3 C6 123.6(4)
N2 C4 C5 113.0(3)
N2 C4 C3 127.2(4)
C5 C4 C3 119.8(4)
N3 C5 C4 114.3(4)
N3 C5 C1 126.4(4)
C4 C5 C1 119.3(3)
C9 C6 C3 130.0(4)
C9 C6 S2 113.2(3)
C3 C6 S2 116.8(3)
C8 C7 S2 113.4(4)
C8 C7 H7 123.3
S2 C7 H7 123.3
C7 C8 C9 115.2(5)
C7 C8 H8 122.4
C9 C8 H8 122.4
C8 C9 C6 107.2(4)
C8 C9 H9 126.4
C6 C9 H9 126.4
C3 N1 C2 121.4(3)
C4 N2 S1 105.9(3)
C5 N3 S1 105.3(3)
N3 S1 N2 101.51(17)
C7 S2 C6 91.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C1 1.875(4)
C1 C2 1.366(5)
C1 C5 1.418(6)
C2 N1 1.359(6)
C2 H2 0.9300
C3 N1 1.336(5)
C3 C4 1.437(5)
C3 C6 1.457(6)
C4 N2 1.356(5)
C4 C5 1.416(6)
C5 N3 1.354(5)
C6 C9 1.443(6)
C6 S2 1.726(4)
C7 C8 1.354(7)
C7 S2 1.695(6)
C7 H7 0.9300
C8 C9 1.431(7)
C8 H8 0.9300
C9 H9 0.9300
N2 S1 1.616(4)
N3 S1 1.616(4)
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
C5 C1 C2 N1 -0.3(7)
Br C1 C2 N1 179.4(4)
N1 C3 C4 N2 -178.8(4)
C6 C3 C4 N2 -0.3(8)
N1 C3 C4 C5 2.2(7)
C6 C3 C4 C5 -179.4(4)
N2 C4 C5 N3 -1.0(6)
C3 C4 C5 N3 178.1(4)
N2 C4 C5 C1 178.8(4)
C3 C4 C5 C1 -2.1(7)
C2 C1 C5 N3 -179.1(4)
Br C1 C5 N3 1.2(6)
C2 C1 C5 C4 1.1(6)
Br C1 C5 C4 -178.6(3)
N1 C3 C6 C9 174.7(4)
C4 C3 C6 C9 -3.7(8)
N1 C3 C6 S2 -6.0(6)
C4 C3 C6 S2 175.6(4)
S2 C7 C8 C9 1.2(7)
C7 C8 C9 C6 -2.2(7)
C3 C6 C9 C8 -178.3(5)
S2 C6 C9 C8 2.4(5)
C4 C3 N1 C2 -1.4(7)
C6 C3 N1 C2 -179.9(4)
C1 C2 N1 C3 0.5(7)
C5 C4 N2 S1 0.6(5)
C3 C4 N2 S1 -178.4(4)
C4 C5 N3 S1 0.9(5)
C1 C5 N3 S1 -178.9(4)
C5 N3 S1 N2 -0.4(3)
C4 N2 S1 N3 -0.1(3)
C8 C7 S2 C6 0.3(5)
C9 C6 S2 C7 -1.6(4)
C3 C6 S2 C7 179.0(4)
