#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:36:53 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178907 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/36/4113685.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_4113685
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 H38 N4 O8 S4'
_chemical_formula_weight         686.86
_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                105.9970(10)
_cell_angle_beta                 91.4790(10)
_cell_angle_gamma                99.2800(10)
_cell_formula_units_Z            1
_cell_length_a                   4.99020(10)
_cell_length_b                   9.4924(2)
_cell_length_c                   16.9038(3)
_cell_measurement_reflns_used    5606
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.51
_cell_volume                     757.55(3)
_computing_cell_refinement       'Siemens SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      158(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_method       'ω 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  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10353
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            needle
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       yellow
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       0.017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.213
_refine_ls_R_factor_all          0.1519
_refine_ls_R_factor_gt           0.1354
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0273P)²+29.4356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3732
_refine_ls_wR_factor_ref         0.3790
_reflns_number_gt                2537
_reflns_number_total             3097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja029216msi20021107_024730_2.cif
_cod_data_source_block           akc(3H2)
_cod_database_code               4113685
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 0.7748(5) 0.4015(3) 0.40864(16) 0.0139(7) Uani 1 1 d .
S2 S 1.2217(6) 0.6548(3) 0.25890(18) 0.0203(7) Uani 1 1 d .
N1 N 0.8262(19) 0.6669(10) 0.3936(6) 0.0176(19) Uani 1 1 d .
N2 N 1.2037(19) 0.3928(10) 0.2762(6) 0.0168(19) Uani 1 1 d .
O1 O 1.6813(17) 0.3162(9) 0.1172(5) 0.0228(18) Uani 1 1 d .
O2 O 1.7045(18) 0.1584(12) -0.1150(5) 0.033(2) Uani 1 1 d .
H2 H 1.8153 0.1273 -0.1493 0.018(7) Uiso 1 1 calc R
O3 O 0.5695(14) 0.8616(8) 0.5719(4) 0.0151(16) Uani 1 1 d .
O4 O 1.1664(17) 1.0719(11) 0.8135(5) 0.029(2) Uani 1 1 d .
H4 H 1.3200 1.1187 0.8352 0.018(7) Uiso 1 1 calc R
C1 C 0.590(2) 0.5233(12) 0.4710(6) 0.015(2) Uani 1 1 d .
C2 C 0.641(2) 0.6592(12) 0.4517(7) 0.015(2) Uani 1 1 d .
C3 C 0.910(2) 0.5392(12) 0.3661(6) 0.015(2) Uani 1 1 d .
C4 C 1.103(2) 0.5157(12) 0.3029(6) 0.016(2) Uani 1 1 d .
C5 C 1.421(2) 0.5401(13) 0.2009(7) 0.020(2) Uani 1 1 d .
H5 H 1.5410 0.5664 0.1624 0.018(7) Uiso 1 1 calc R
C6 C 1.384(2) 0.4083(13) 0.2174(7) 0.017(2) Uani 1 1 d .
C7 C 1.519(2) 0.2790(13) 0.1791(7) 0.021(2) Uani 1 1 d .
H7A H 1.6348 0.2580 0.2214 0.018(7) Uiso 1 1 calc R
H7B H 1.3803 0.1893 0.1541 0.018(7) Uiso 1 1 calc R
C8 C 1.808(2) 0.1965(13) 0.0731(7) 0.022(2) Uani 1 1 d .
H8A H 1.6688 0.1117 0.0416 0.018(7) Uiso 1 1 calc R
H8B H 1.9157 0.1622 0.1119 0.018(7) Uiso 1 1 calc R
C9 C 1.992(2) 0.2539(14) 0.0151(7) 0.024(3) Uani 1 1 d .
H9A H 2.1045 0.1785 -0.0096 0.018(7) Uiso 1 1 calc R
H9B H 2.1165 0.3451 0.0472 0.018(7) Uiso 1 1 calc R
C10 C 1.838(3) 0.2894(15) -0.0538(7) 0.030(3) Uani 1 1 d .
H10A H 1.7004 0.3501 -0.0299 0.018(7) Uiso 1 1 calc R
H10B H 1.9669 0.3493 -0.0805 0.018(7) Uiso 1 1 calc R
C11 C 0.514(2) 0.7958(12) 0.4868(7) 0.018(2) Uani 1 1 d .
H11A H 0.5797 0.8709 0.4579 0.018(7) Uiso 1 1 calc R
H11B H 0.3144 0.7678 0.4749 0.018(7) Uiso 1 1 calc R
C12 C 0.845(2) 0.9268(12) 0.5963(7) 0.019(2) Uani 1 1 d .
H12A H 0.8922 1.0190 0.5793 0.018(7) Uiso 1 1 calc R
H12B H 0.9662 0.8570 0.5702 0.018(7) Uiso 1 1 calc R
C13 C 0.880(2) 0.9619(12) 0.6897(7) 0.017(2) Uani 1 1 d .
H13A H 0.8280 0.8687 0.7055 0.018(7) Uiso 1 1 calc R
H13B H 0.7546 1.0301 0.7146 0.018(7) Uiso 1 1 calc R
C14 C 1.170(2) 1.0333(14) 0.7250(7) 0.023(3) Uani 1 1 d .
H14A H 1.2967 0.9626 0.7058 0.018(7) Uiso 1 1 calc R
H14B H 1.2310 1.1234 0.7070 0.018(7) Uiso 1 1 calc R
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
C3 S1 C1 89.7(5) . .
C5 S2 C4 88.8(5) . .
C3 N1 C2 110.5(9) . .
C4 N2 C6 109.6(9) . .
C7 O1 C8 112.6(9) . .
C11 O3 C12 114.6(8) . .
C2 C1 C1 130.1(12) . 2_666
C2 C1 S1 108.5(7) . .
C1 C1 S1 121.4(11) 2_666 .
N1 C2 C1 115.3(9) . .
N1 C2 C11 117.1(9) . .
C1 C2 C11 127.5(9) . .
N1 C3 C4 121.9(9) . .
N1 C3 S1 115.9(8) . .
C4 C3 S1 122.1(8) . .
N2 C4 C3 124.4(9) . .
N2 C4 S2 115.2(8) . .
C3 C4 S2 120.4(8) . .
C6 C5 S2 110.5(8) . .
C5 C6 N2 115.8(10) . .
C5 C6 C7 126.6(10) . .
N2 C6 C7 117.6(10) . .
O1 C7 C6 107.9(9) . .
O1 C8 C9 107.4(10) . .
C8 C9 C10 113.4(10) . .
O2 C10 C9 112.6(11) . .
O3 C11 C2 115.0(9) . .
O3 C12 C13 107.3(8) . .
C12 C13 C14 113.0(9) . .
O4 C14 C13 106.7(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.714(11) .
S1 C1 1.737(11) .
S2 C5 1.718(11) .
S2 C4 1.720(11) .
N1 C3 1.312(14) .
N1 C2 1.374(14) .
N2 C4 1.314(14) .
N2 C6 1.380(13) .
O1 C7 1.423(13) .
O1 C8 1.428(14) .
O2 C10 1.430(15) .
O3 C11 1.400(13) .
O3 C12 1.415(13) .
O4 C14 1.440(14) .
C1 C2 1.402(15) .
C1 C1 1.46(2) 2_666
C2 C11 1.515(14) .
C3 C4 1.455(14) .
C5 C6 1.341(16) .
C6 C7 1.493(15) .
C8 C9 1.508(16) .
C9 C10 1.522(17) .
C12 C13 1.521(15) .
C13 C14 1.528(16) .
