#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:36:53 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178907 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/36/4113684.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_4113684
loop_
_publ_author_name
'Amy B. Koren'
'M. David Curtis'
'Anthony H. Francis'
'Jeff W. Kampf'
_publ_section_title
;
 Intermolecular Interactions in π-Stacked Conjugated Molecules.
 Synthesis, Structure, and Spectral Characterization of Alkyl Bithiazole
 Oligomers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5040
_journal_page_last               5050
_journal_paper_doi               10.1021/ja029216m
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C28 H30 N4 O4 S4'
_chemical_formula_weight         614.80
_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                71.1000(10)
_cell_angle_beta                 88.3450(10)
_cell_angle_gamma                89.7350(10)
_cell_formula_units_Z            2
_cell_length_a                   4.71770(10)
_cell_length_b                   16.96430(10)
_cell_length_c                   19.44940(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      1.11
_cell_volume                     1472.03(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 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19477
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.11
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       plate
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.0003(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         5810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0662P)²+0.0580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                4522
_reflns_number_total             5810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja029216msi20021107_024730_1.cif
_cod_data_source_block           akb(3P2)
_cod_database_code               4113684
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
S1 S -0.18972(13) 0.09786(3) 0.49861(3) 0.02236(17) Uani 1 1 d .
S2 S 0.13198(14) 0.12143(3) 0.69987(3) 0.02296(17) Uani 1 1 d .
O1 O -0.5460(4) -0.15738(9) 0.64829(9) 0.0261(4) Uani 1 1 d .
O2 O 0.7188(4) 0.33645(10) 0.60825(9) 0.0362(5) Uani 1 1 d .
N1 N -0.2899(4) 0.02951(11) 0.63576(10) 0.0221(4) Uani 1 1 d .
N2 N 0.2147(4) 0.19968(11) 0.56293(10) 0.0222(4) Uani 1 1 d .
C1 C -0.4311(5) 0.01554(13) 0.52622(12) 0.0205(5) Uani 1 1 d .
C2 C -0.4580(5) -0.01129(13) 0.60134(13) 0.0204(5) Uani 1 1 d .
C3 C -0.6505(6) -0.07857(15) 0.64841(14) 0.0246(5) Uani 1 1 d .
H3A H -0.646(6) -0.0763(14) 0.6977(15) 0.028(7) Uiso 1 1 d .
H3B H -0.843(6) -0.0718(15) 0.6300(15) 0.034(7) Uiso 1 1 d .
C4 C -0.7392(7) -0.22264(16) 0.68553(16) 0.0328(6) Uani 1 1 d .
H4A H -0.935(7) -0.2079(16) 0.6668(15) 0.033(8) Uiso 1 1 d .
H4B H -0.751(6) -0.2273(16) 0.7366(16) 0.038(8) Uiso 1 1 d .
C5 C -0.6480(8) -0.30213(17) 0.67373(17) 0.0455(8) Uani 1 1 d .
H5 H -0.759(7) -0.3488(19) 0.7023(17) 0.055(9) Uiso 1 1 d .
C6 C -0.4501(9) -0.3094(2) 0.6279(2) 0.0520(9) Uani 1 1 d .
H6A H -0.336(7) -0.2616(19) 0.6010(17) 0.050(9) Uiso 1 1 d .
H6B H -0.422(7) -0.366(2) 0.6204(17) 0.055(9) Uiso 1 1 d .
C7 C -0.1368(5) 0.08732(13) 0.58830(12) 0.0208(5) Uani 1 1 d .
C8 C 0.0678(5) 0.13867(13) 0.60928(12) 0.0204(5) Uani 1 1 d .
C9 C 0.3729(6) 0.20115(14) 0.67416(13) 0.0235(5) Uani 1 1 d .
H9 H 0.486(6) 0.2158(16) 0.7087(16) 0.037(8) Uiso 1 1 d .
C10 C 0.3892(5) 0.23520(14) 0.60052(13) 0.0228(5) Uani 1 1 d .
C11 C 0.5757(6) 0.30641(15) 0.55828(14) 0.0264(6) Uani 1 1 d .
H11A H 0.711(6) 0.2854(16) 0.5289(15) 0.035(8) Uiso 1 1 d .
H11B H 0.460(5) 0.3523(14) 0.5253(13) 0.021(6) Uiso 1 1 d .
C12 C 0.8719(7) 0.41125(17) 0.57310(16) 0.0360(7) Uani 1 1 d .
H12A H 0.728(7) 0.4578(18) 0.5539(16) 0.043(8) Uiso 1 1 d .
H12B H 0.981(7) 0.4060(18) 0.5331(18) 0.050(9) Uiso 1 1 d .
C13 C 1.0677(9) 0.4277(2) 0.62600(19) 0.0550(9) Uani 1 1 d .
H13 H 1.247(9) 0.386(2) 0.651(2) 0.086(13) Uiso 1 1 d .
C14 C 1.0786(10) 0.4917(2) 0.6446(2) 0.0767(13) Uani 1 1 d .
H14A H 0.9528 0.5366 0.6243 0.134(9) Uiso 1 1 calc R
H14B H 1.2127 0.4954 0.6789 0.134(9) Uiso 1 1 calc R
S3 S -0.11110(14) 0.27158(4) -0.20780(3) 0.02555(17) Uani 1 1 d .
S4 S 0.18844(13) 0.09895(3) -0.00303(3) 0.02187(16) Uani 1 1 d .
O3 O -0.7293(4) 0.41578(11) -0.11868(11) 0.0370(5) Uani 1 1 d .
O4 O 0.5563(4) -0.05888(9) -0.14029(9) 0.0234(4) Uani 1 1 d .
N3 N -0.2165(4) 0.24606(11) -0.07134(11) 0.0232(5) Uani 1 1 d .
N4 N 0.2937(4) 0.12586(11) -0.13934(10) 0.0212(4) Uani 1 1 d .
C15 C -0.3590(6) 0.33248(15) -0.18346(14) 0.0264(6) Uani 1 1 d .
H15 H -0.457(6) 0.3753(16) -0.2181(15) 0.031(7) Uiso 1 1 d .
C16 C -0.3873(5) 0.31073(14) -0.10993(14) 0.0248(5) Uani 1 1 d .
C17 C -0.5788(6) 0.35073(16) -0.06854(15) 0.0296(6) Uani 1 1 d .
H17A H -0.711(6) 0.3086(14) -0.0390(13) 0.020(6) Uiso 1 1 d .
H17B H -0.462(6) 0.3762(14) -0.0381(14) 0.026(7) Uiso 1 1 d .
C18 C -0.8843(7) 0.46462(19) -0.08399(19) 0.0447(8) Uani 1 1 d .
H18A H -0.738(6) 0.4956(16) -0.0608(15) 0.035(7) Uiso 1 1 d .
H18B H -0.990(7) 0.4258(18) -0.0430(17) 0.050(9) Uiso 1 1 d .
C19 C -1.0788(7) 0.52117(18) -0.1388(2) 0.0550(9) Uani 1 1 d .
H19 H -1.1842 0.4965 -0.1675 0.134(9) Uiso 1 1 calc R
C20 C -1.1141(10) 0.5981(2) -0.1500(2) 0.0744(12) Uani 1 1 d .
H20A H -1.0131 0.6254 -0.1226 0.134(9) Uiso 1 1 calc R
H20B H -1.2415 0.6286 -0.1858 0.134(9) Uiso 1 1 calc R
C21 C -0.0622(5) 0.21969(13) -0.11662(12) 0.0214(5) Uani 1 1 d .
C22 C 0.1399(5) 0.15196(13) -0.09361(12) 0.0207(5) Uani 1 1 d .
C23 C 0.4307(5) 0.03431(13) -0.02728(12) 0.0195(5) Uani 1 1 d .
C24 C 0.4586(5) 0.05941(13) -0.10242(12) 0.0204(5) Uani 1 1 d .
C25 C 0.6501(6) 0.02296(14) -0.14692(13) 0.0234(5) Uani 1 1 d .
H25A H 0.654(6) 0.0596(15) -0.1988(15) 0.031(7) Uiso 1 1 d .
H25B H 0.847(6) 0.0201(14) -0.1314(13) 0.021(6) Uiso 1 1 d .
C26 C 0.7547(6) -0.09831(16) -0.17504(15) 0.0295(6) Uani 1 1 d .
H26A H 0.948(7) -0.0966(15) -0.1556(15) 0.036(8) Uiso 1 1 d .
H26B H 0.763(6) -0.0676(16) -0.2266(16) 0.036(8) Uiso 1 1 d .
C27 C 0.6671(7) -0.18678(17) -0.16112(16) 0.0381(7) Uani 1 1 d .
H27 H 0.766(7) -0.2130(19) -0.1880(18) 0.057(10) Uiso 1 1 d .
C28 C 0.4664(7) -0.22709(18) -0.11614(17) 0.0398(7) Uani 1 1 d .
H28A H 0.362(6) -0.2010(16) -0.0882(16) 0.033(8) Uiso 1 1 d .
H28B H 0.420(6) -0.2846(16) -0.1106(14) 0.032(7) 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'
O O 0.0106 0.0060 '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
C7 S1 C1 89.47(11) . .
C9 S2 C8 88.84(11) . .
C3 O1 C4 111.1(2) . .
C12 O2 C11 112.4(2) . .
C7 N1 C2 110.7(2) . .
C8 N2 C10 109.4(2) . .
C2 C1 C1 129.6(3) . 2_456
C2 C1 S1 108.83(16) . .
C1 C1 S1 121.6(2) 2_456 .
N1 C2 C1 115.5(2) . .
N1 C2 C3 117.2(2) . .
C1 C2 C3 127.3(2) . .
O1 C3 C2 109.0(2) . .
O1 C4 C5 109.7(2) . .
C6 C5 C4 125.9(3) . .
N1 C7 C8 122.8(2) . .
N1 C7 S1 115.41(18) . .
C8 C7 S1 121.74(18) . .
N2 C8 C7 124.2(2) . .
N2 C8 S2 115.50(17) . .
C7 C8 S2 120.30(17) . .
C10 C9 S2 110.67(19) . .
C9 C10 N2 115.5(2) . .
C9 C10 C11 125.9(2) . .
N2 C10 C11 118.5(2) . .
O2 C11 C10 108.4(2) . .
O2 C12 C13 108.9(2) . .
C14 C13 C12 127.3(4) . .
C15 S3 C21 88.69(12) . .
C22 S4 C23 89.57(11) . .
C18 O3 C17 112.1(2) . .
C25 O4 C26 110.50(18) . .
C21 N3 C16 109.7(2) . .
C22 N4 C24 110.61(19) . .
C16 C15 S3 110.77(19) . .
C15 C16 N3 115.3(2) . .
C15 C16 C17 126.3(2) . .
N3 C16 C17 118.4(2) . .
O3 C17 C16 108.8(2) . .
O3 C18 C19 108.2(3) . .
C20 C19 C18 126.0(4) . .
N3 C21 C22 123.6(2) . .
N3 C21 S3 115.57(18) . .
C22 C21 S3 120.77(18) . .
N4 C22 C21 123.3(2) . .
N4 C22 S4 115.35(17) . .
C21 C22 S4 121.34(18) . .
C24 C23 C23 129.4(3) . 2_655
C24 C23 S4 108.84(16) . .
C23 C23 S4 121.8(2) 2_655 .
N4 C24 C23 115.6(2) . .
N4 C24 C25 117.2(2) . .
C23 C24 C25 127.1(2) . .
O4 C25 C24 109.73(19) . .
O4 C26 C27 109.6(2) . .
C28 C27 C26 126.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.720(2) .
S1 C1 1.740(2) .
S2 C9 1.707(2) .
S2 C8 1.726(2) .
O1 C3 1.423(3) .
O1 C4 1.426(3) .
O2 C12 1.420(3) .
O2 C11 1.422(3) .
N1 C7 1.310(3) .
N1 C2 1.375(3) .
N2 C8 1.315(3) .
N2 C10 1.378(3) .
C1 C2 1.385(3) .
C1 C1 1.460(4) 2_456
C2 C3 1.500(3) .
C4 C5 1.498(4) .
C5 C6 1.305(5) .
C7 C8 1.455(3) .
C9 C10 1.360(3) .
C10 C11 1.494(3) .
C12 C13 1.494(5) .
C13 C14 1.252(5) .
S3 C15 1.713(3) .
S3 C21 1.727(2) .
S4 C22 1.721(2) .
S4 C23 1.739(2) .
O3 C18 1.416(3) .
O3 C17 1.417(3) .
O4 C25 1.424(3) .
O4 C26 1.425(3) .
N3 C21 1.312(3) .
N3 C16 1.382(3) .
N4 C22 1.315(3) .
N4 C24 1.375(3) .
C15 C16 1.359(4) .
C16 C17 1.494(4) .
C18 C19 1.511(5) .
C19 C20 1.262(4) .
C21 C22 1.453(3) .
C23 C24 1.386(3) .
C23 C23 1.463(4) 2_655
C24 C25 1.498(3) .
C26 C27 1.494(4) .
C27 C28 1.304(4) .
