#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:19:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178894 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/23/4112393.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_4112393
loop_
_publ_author_name
'M. David Curtis'
'Jie Cao'
'Jeff W. Kampf'
_publ_section_title
;
 Solid-State Packing of Conjugated Oligomers: From π-Stacks to the
 Herringbone Structure
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4318
_journal_page_last               4328
_journal_paper_doi               10.1021/ja0397916
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C20 H22 N4 S4'
_chemical_formula_weight         446.66
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.0390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.497(2)
_cell_length_b                   5.3135(5)
_cell_length_c                   18.5971(17)
_cell_measurement_reflns_used    5434
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.35
_cell_volume                     2074.9(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      158(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19595
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0339
_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)+(0.0400P)²+3.2448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                1916
_reflns_number_total             2130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0397916si20031125_105647.cif
_cod_data_source_block           ebt2
_cod_database_code               4112393
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'
'-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
S1 S 0.17350(2) 0.51474(9) 0.01288(3) 0.02079(14) Uani 1 1 d
S2 S 0.21445(2) -0.07550(9) 0.18803(3) 0.02483(15) Uani 1 1 d
N1 N 0.27199(7) 0.3326(3) 0.11835(9) 0.0222(3) Uani 1 1 d
N2 N 0.11351(8) 0.0835(3) 0.08031(10) 0.0253(4) Uani 1 1 d
C1 C 0.24731(8) 0.6465(3) 0.02437(10) 0.0185(4) Uani 1 1 d
C2 C 0.29398(9) 0.5204(4) 0.08332(11) 0.0223(4) Uani 1 1 d
C3 C 0.36498(9) 0.5637(4) 0.11540(12) 0.0270(4) Uani 1 1 d
H3A H 0.3801(10) 0.608(4) 0.0750(13) 0.029(6) Uiso 1 1 d
H3B H 0.3858(10) 0.401(4) 0.1359(12) 0.019(5) Uiso 1 1 d
C4 C 0.38432(11) 0.7525(5) 0.18087(13) 0.0355(5) Uani 1 1 d
H4A H 0.3636(13) 0.921(6) 0.1584(16) 0.049(8) Uiso 1 1 d
H4B H 0.4305(13) 0.770(6) 0.2011(15) 0.052(8) Uiso 1 1 d
H4C H 0.3695(13) 0.689(5) 0.2219(16) 0.051(8) Uiso 1 1 d
C5 C 0.21018(9) 0.3096(3) 0.08702(10) 0.0195(4) Uani 1 1 d
C6 C 0.17480(9) 0.1213(3) 0.11197(10) 0.0201(4) Uani 1 1 d
C7 C 0.14325(9) -0.2161(4) 0.17671(11) 0.0242(4) Uani 1 1 d
H7 H 0.1425(11) -0.342(5) 0.2105(15) 0.041(7) Uiso 1 1 d
C8 C 0.09519(9) -0.1121(4) 0.11727(12) 0.0255(4) Uani 1 1 d
C9 C 0.02632(11) -0.1898(5) 0.08836(16) 0.0418(6) Uani 1 1 d
H9A H 0.0139(13) -0.249(6) 0.0332(18) 0.060(9) Uiso 1 1 d
H9B H 0.0016(16) -0.041(7) 0.0872(19) 0.075(11) Uiso 1 1 d
C10 C 0.01152(12) -0.4052(5) 0.13229(18) 0.0443(6) Uani 1 1 d
H10A H 0.0332(15) -0.548(6) 0.1257(18) 0.059(9) Uiso 1 1 d
H10B H -0.0323(15) -0.454(6) 0.1110(16) 0.057(8) Uiso 1 1 d
H10C H 0.0228(14) -0.354(6) 0.1871(18) 0.060(9) Uiso 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'
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
C5 S1 C1 89.68(9) . .
C7 S2 C6 88.74(9) . .
C5 N1 C2 111.25(16) . .
C6 N2 C8 110.20(16) . .
C2 C1 C1 130.3(2) . 7_565
C2 C1 S1 108.66(13) . .
C1 C1 S1 120.99(18) 7_565 .
N1 C2 C1 115.17(16) . .
N1 C2 C3 115.63(17) . .
C1 C2 C3 129.19(17) . .
C2 C3 C4 112.11(18) . .
N1 C5 C6 122.61(17) . .
N1 C5 S1 115.23(14) . .
C6 C5 S1 122.15(14) . .
N2 C6 C5 124.91(17) . .
N2 C6 S2 115.29(14) . .
C5 C6 S2 119.78(14) . .
C8 C7 S2 111.09(15) . .
C7 C8 N2 114.67(17) . .
C7 C8 C9 126.67(19) . .
N2 C8 C9 118.66(18) . .
C8 C9 C10 114.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C5 1.7184(19) .
S1 C1 1.7431(18) .
S2 C7 1.711(2) .
S2 C6 1.7275(19) .
N1 C5 1.306(2) .
N1 C2 1.377(2) .
N2 C6 1.306(2) .
N2 C8 1.387(2) .
C1 C2 1.388(3) .
C1 C1 1.458(4) 7_565
C2 C3 1.509(3) .
C3 C4 1.516(3) .
C5 C6 1.455(3) .
C7 C8 1.356(3) .
C8 C9 1.504(3) .
C9 C10 1.511(3) .
