#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/72/4107287.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_4107287
loop_
_publ_author_name
'Nicolas Blouin'
'Alexandre Michaud'
'David Gendron'
'Salem Wakim'
'Emily Blair'
'Rodica Neagu-Plesu'
'Michel Belletête'
'Gilles Durocher'
'Ye Tao'
'Mario Leclerc'
_publ_contact_author_address
;
      
      Département de Chimie
      Pavillon Alexandre-Vachon, Local 2240-D
      Université Laval
      Québec, Canada
      G1K 7P4
;
_publ_contact_author_email       mario.leclerc@chm.ulaval.ca
_publ_contact_author_fax         418-656-7916
_publ_contact_author_name        'Mario Leclerc'
_publ_contact_author_phone       '418 656-5140'
_publ_section_title
;
 Toward a Rational Design of Poly(2,7-Carbazole) Derivatives for Solar
 Cells
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              732
_journal_page_last               742
_journal_paper_doi               10.1021/ja0771989
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C5 H Br Cl N3 S'
_chemical_formula_sum            'C5 H Br Cl N3 S'
_chemical_formula_weight         250.51
_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                 90.057(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.970(3)
_cell_length_b                   17.147(13)
_cell_length_c                   10.871(8)
_cell_measurement_reflns_used    3204
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      2.22
_cell_volume                     740.0(10)
_computing_cell_refinement       'APEX 2 (Bruker, 2005b)'
_computing_data_collection       'APEX 2 (Bruker, 2005b)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Smart APEX II CCD'
_diffrn_measurement_method       ω
_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  0.0547
_diffrn_reflns_av_sigmaI/netI    0.1226
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6688
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    6.122
_exptl_absorpt_correction_T_max  0.9413
_exptl_absorpt_correction_T_min  0.8376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.248
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.646
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1287
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0559
_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)+(0.0320P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                980
_reflns_number_total             1287
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0771989-file002.cif
_cod_data_source_block           mle011b
_cod_database_code               4107287
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
Br1 Br 0.5284(4) 0.46827(6) 0.81646(12) 0.0458(4) Uani 1 1 d U
Cl1 Cl 0.0848(8) 0.13989(15) 0.5993(3) 0.0458(8) Uani 1 1 d U
S1 S -0.0960(8) 0.39306(15) 0.4521(3) 0.0381(8) Uani 1 1 d U
N1 N 0.101(2) 0.4302(5) 0.5676(8) 0.039(2) Uani 1 1 d U
N2 N -0.069(3) 0.3017(4) 0.4837(8) 0.036(2) Uani 1 1 d U
C1 C 0.198(3) 0.3707(6) 0.6389(10) 0.029(2) Uani 1 1 d U
C2 C 0.387(3) 0.3730(5) 0.7470(10) 0.028(2) Uani 1 1 d U
C3 C 0.473(3) 0.3044(6) 0.8009(9) 0.036(3) Uani 1 1 d U
H3 H 0.6040 0.3060 0.8741 0.043 Uiso 1 1 calc R
N4 N 0.383(2) 0.2335(5) 0.7561(8) 0.034(2) Uani 1 1 d U
C5 C 0.204(3) 0.2294(6) 0.6550(11) 0.034(3) Uani 1 1 d U
C6 C 0.104(3) 0.2969(6) 0.5892(9) 0.030(3) Uani 1 1 d U
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0537(8) 0.0327(5) 0.0512(7) -0.0120(5) -0.0127(9) -0.0034(6)
Cl1 0.0580(19) 0.0207(12) 0.0586(17) -0.0003(12) -0.0096(16) -0.0023(13)
S1 0.0492(19) 0.0293(13) 0.0357(14) 0.0025(11) -0.0085(15) 0.0042(13)
N1 0.042(4) 0.031(4) 0.044(4) 0.007(3) -0.005(4) 0.001(3)
N2 0.041(4) 0.032(3) 0.037(4) -0.003(3) -0.009(4) 0.002(4)
C1 0.029(4) 0.022(4) 0.036(4) 0.001(3) -0.003(4) -0.002(3)
C2 0.030(4) 0.024(4) 0.030(4) -0.006(3) 0.001(4) 0.000(3)
C3 0.038(5) 0.035(4) 0.035(4) -0.001(3) -0.003(4) 0.000(4)
N4 0.043(4) 0.026(4) 0.034(4) 0.007(3) -0.002(3) 0.001(3)
C5 0.036(4) 0.024(4) 0.040(5) -0.006(4) 0.002(4) 0.001(4)
C6 0.032(4) 0.033(4) 0.027(4) 0.005(3) -0.003(4) 0.001(4)
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'
Cl Cl 0.1484 0.1585 '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
N2 S1 N1 100.8(4)
C1 N1 S1 106.8(7)
C6 N2 S1 106.1(7)
N1 C1 C2 128.4(9)
N1 C1 C6 112.6(9)
C2 C1 C6 119.0(9)
C3 C2 C1 118.3(9)
C3 C2 Br1 120.3(8)
C1 C2 Br1 121.5(7)
N4 C3 C2 123.7(9)
N4 C3 H3 118.2
C2 C3 H3 118.1
C5 N4 C3 119.5(9)
N4 C5 C6 122.1(9)
N4 C5 Cl1 119.6(8)
C6 C5 Cl1 118.4(8)
N2 C6 C5 128.7(10)
N2 C6 C1 113.7(9)
C5 C6 C1 117.5(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.884(9)
Cl1 C5 1.716(10)
S1 N2 1.607(8)
S1 N1 1.609(9)
N1 C1 1.338(13)
N2 C6 1.340(12)
C1 C2 1.395(14)
C1 C6 1.425(14)
C2 C3 1.359(13)
C3 N4 1.358(12)
C3 H3 0.9500
N4 C5 1.309(13)
C5 C6 1.417(14)
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
N2 S1 N1 C1 -0.4(9)
N1 S1 N2 C6 -0.6(9)
S1 N1 C1 C2 177.4(10)
S1 N1 C1 C6 1.3(12)
N1 C1 C2 C3 -176.2(11)
C6 C1 C2 C3 -0.4(16)
N1 C1 C2 Br1 2.8(17)
C6 C1 C2 Br1 178.7(9)
C1 C2 C3 N4 -0.6(18)
Br1 C2 C3 N4 -179.6(9)
C2 C3 N4 C5 0.4(17)
C3 N4 C5 C6 0.8(16)
C3 N4 C5 Cl1 -179.1(9)
S1 N2 C6 C5 -178.3(10)
S1 N2 C6 C1 1.4(12)
N4 C5 C6 N2 178.0(11)
Cl1 C5 C6 N2 -2.1(18)
N4 C5 C6 C1 -1.6(17)
Cl1 C5 C6 C1 178.3(9)
N1 C1 C6 N2 -1.8(15)
C2 C1 C6 N2 -178.3(11)
N1 C1 C6 C5 177.9(9)
C2 C1 C6 C5 1.4(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660295
