#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/95/4109565.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_4109565
loop_
_publ_author_name
'Alicea A. Leitch'
'Robert W. Reed'
'Craig M. Robertson'
'James F. Britten'
'Xueyang Yu'
'Richard A. Secco'
'Richard T. Oakley'
_publ_contact_author             'Professor Richard Oakley'
_publ_contact_author_email       oakley@uwaterloo.ca
_publ_section_title
;
 An Alternating π-Stacked Bisdithiazolyl Radical Conductor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7903
_journal_page_last               7914
_journal_paper_doi               10.1021/ja071218p
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C5 H3 N4 S4'
_chemical_formula_sum            'C5 H3 N4 S4'
_chemical_formula_weight         247.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.6488(2)
_cell_length_b                   27.2177(5)
_cell_length_c                   9.2797(2)
_cell_measurement_reflns_used    2159
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      67.54
_cell_measurement_theta_min      3.25
_cell_volume                     1679.30(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'cross-coupled parallel focusing mirrors'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4138
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    10.015
_exptl_absorpt_correction_T_max  0.9065
_exptl_absorpt_correction_T_min  0.1729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.957
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0386
_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)+(0.0830P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                693
_reflns_number_total             829
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071218psi20070222_084209.cif
_cod_data_source_block           bpzme0m
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_database_code               4109565
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, 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
S1 S 0.5000 0.20016(3) -0.04769(10) 0.0603(4) Uani 1 2 d S
C2 C 0.5000 0.18415(13) 0.2448(4) 0.0442(9) Uani 1 2 d S
N1 N 0.5000 0.14328(12) 0.0164(4) 0.0539(9) Uani 1 2 d S
S2 S 0.5000 0.23833(4) 0.14527(9) 0.0532(4) Uani 1 2 d S
N2 N 0.5000 0.09594(10) 0.2259(3) 0.0422(7) Uani 1 2 d S
C1 C 0.5000 0.14140(13) 0.1553(4) 0.0417(9) Uani 1 2 d S
C4 C 0.5000 0.09443(13) 0.3745(4) 0.0403(8) Uani 1 2 d S
S4 S 0.5000 0.13435(4) 0.63643(10) 0.0586(4) Uani 1 2 d S
N3 N 0.5000 0.05264(11) 0.4423(3) 0.0474(8) Uani 1 2 d S
N4 N 0.5000 0.18465(11) 0.3877(3) 0.0462(8) Uani 1 2 d S
C3 C 0.5000 0.14078(13) 0.4513(4) 0.0423(8) Uani 1 2 d S
S3 S 0.5000 0.05766(4) 0.62133(11) 0.0602(4) Uani 1 2 d S
C5 C 0.5000 0.05023(14) 0.1407(4) 0.0493(9) Uani 1 2 d S
H1A H 0.5000 0.0581 0.0399 0.074 Uiso 0.50 2 calc SPR
H2A H 0.3821 0.0314 0.1634 0.074 Uiso 0.25 1 calc PR
H3A H 0.6179 0.0314 0.1634 0.074 Uiso 0.25 1 calc PR
H4A H 0.5000 0.0225 0.2045 0.074 Uiso 0.50 2 calc SPR
H5A H 0.6179 0.0492 0.0810 0.074 Uiso 0.25 1 calc PR
H6A H 0.3821 0.0492 0.0810 0.074 Uiso 0.25 1 calc PR
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
S1 0.1099(9) 0.0417(6) 0.0293(6) 0.0042(4) 0.000 0.000
C2 0.060(2) 0.0369(19) 0.036(2) 0.0050(15) 0.000 0.000
N1 0.085(2) 0.0399(17) 0.0366(19) -0.0003(13) 0.000 0.000
S2 0.0938(8) 0.0339(5) 0.0319(6) 0.0037(3) 0.000 0.000
N2 0.0582(18) 0.0317(15) 0.0366(18) -0.0007(11) 0.000 0.000
C1 0.051(2) 0.0347(19) 0.040(2) 0.0023(13) 0.000 0.000
C4 0.042(2) 0.040(2) 0.038(2) 0.0049(14) 0.000 0.000
S4 0.0995(9) 0.0460(6) 0.0302(6) 0.0040(4) 0.000 0.000
N3 0.065(2) 0.0379(16) 0.0390(18) 0.0080(13) 0.000 0.000
N4 0.069(2) 0.0345(16) 0.0349(18) 0.0004(13) 0.000 0.000
C3 0.055(2) 0.0389(19) 0.033(2) 0.0034(14) 0.000 0.000
S3 0.0963(9) 0.0456(6) 0.0387(6) 0.0120(4) 0.000 0.000
C5 0.068(2) 0.039(2) 0.041(2) -0.0036(15) 0.000 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 S1 S2 99.10(12)
N4 C2 C1 126.1(3)
N4 C2 S2 121.5(3)
C1 C2 S2 112.4(3)
C1 N1 S1 113.3(3)
C2 S2 S1 91.93(13)
C4 N2 C1 119.6(3)
C4 N2 C5 120.7(3)
C1 N2 C5 119.7(3)
N1 C1 N2 120.2(3)
N1 C1 C2 123.2(3)
N2 C1 C2 116.6(3)
N3 C4 N2 120.6(3)
N3 C4 C3 121.6(3)
N2 C4 C3 117.8(3)
C3 S4 S3 91.97(12)
C4 N3 S3 114.2(3)
C2 N4 C3 115.7(3)
N4 C3 C4 124.2(3)
N4 C3 S4 122.1(3)
C4 C3 S4 113.7(3)
N3 S3 S4 98.54(11)
N2 C5 H1A 109.5
N2 C5 H2A 109.5
H1A C5 H2A 109.5
N2 C5 H3A 109.5
H1A C5 H3A 109.5
H2A C5 H3A 109.5
N2 C5 H4A 109.5
H1A C5 H4A 141.1
H2A C5 H4A 56.3
H3A C5 H4A 56.3
N2 C5 H5A 109.5
H1A C5 H5A 56.3
H2A C5 H5A 141.1
H3A C5 H5A 56.3
H4A C5 H5A 109.5
N2 C5 H6A 109.5
H1A C5 H6A 56.3
H2A C5 H6A 56.3
H3A C5 H6A 141.1
H4A C5 H6A 109.5
H5A C5 H6A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.658(3)
S1 S2 2.0702(14)
C2 N4 1.326(4)
C2 C1 1.429(5)
C2 S2 1.740(4)
N1 C1 1.290(5)
N2 C4 1.380(4)
N2 C1 1.400(4)
N2 C5 1.474(4)
C4 N3 1.300(4)
C4 C3 1.449(5)
S4 C3 1.726(4)
S4 S3 2.0923(15)
N3 S3 1.667(3)
N4 C3 1.332(4)
C5 H1A 0.9600
C5 H2A 0.9600
C5 H3A 0.9600
C5 H4A 0.9600
C5 H5A 0.9600
C5 H6A 0.9600
