# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Yunqi Liu'
_publ_contact_author_email       LIUYQ@MAIL.ICCAS.AC.CN

_publ_section_title              
;
Unusual tubular organization with crystal stacks
from new cyclic thiophene compound
;
loop_
_publ_author_name
'Yunqi Liu'
'Chong-an Di'
'Chunyan Du'
'Hongtao Liu'
'Kun Lu'
'Ti Wu'
'Xudong Xu'
'Shanghui Ye'
'Gui Yu'

# Attachment 'cif.cif'

data_60915b
_database_code_depnum_ccdc_archive 'CCDC 623892'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 S6'
_chemical_formula_weight         392.58

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   8.5563(11)
_cell_length_b                   11.8407(15)
_cell_length_c                   16.475(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.639(2)
_cell_angle_gamma                90.00
_cell_volume                     1650.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4399
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.30

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.777604
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            9110
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.38
_reflns_number_total             3373
_reflns_number_gt                2679
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0390P)²+0.3486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0325(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3373
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.91057(7) 1.00831(5) 0.11454(4) 0.05245(18) Uani 1 1 d . . .
S2 S 0.67069(7) 1.01537(4) 0.26818(3) 0.04262(16) Uani 1 1 d . . .
S3 S 0.87278(6) 0.67513(5) 0.20792(3) 0.04222(15) Uani 1 1 d . . .
S4 S 0.48593(6) 0.73677(4) 0.11439(3) 0.03863(15) Uani 1 1 d . . .
S5 S 0.76216(7) 0.46567(5) -0.00597(4) 0.04905(17) Uani 1 1 d . . .
S6 S 0.75035(7) 0.73540(5) -0.08601(3) 0.04578(16) Uani 1 1 d . . .
C1 C 1.0631(3) 0.9242(3) 0.09367(14) 0.0600(7) Uani 1 1 d . . .
H1 H 1.1462 0.9499 0.0682 0.072 Uiso 1 1 calc R . .
C2 C 1.0490(2) 0.8171(2) 0.11819(13) 0.0497(6) Uani 1 1 d . . .
H2 H 1.1203 0.7601 0.1108 0.060 Uiso 1 1 calc R . .
C3 C 0.9117(2) 0.80034(17) 0.15701(11) 0.0351(4) Uani 1 1 d . . .
C4 C 0.8234(2) 0.89651(16) 0.15864(11) 0.0338(4) Uani 1 1 d . . .
C5 C 0.6780(2) 0.91225(15) 0.19392(11) 0.0325(4) Uani 1 1 d . . .
C6 C 0.5403(2) 0.85021(16) 0.18254(11) 0.0332(4) Uani 1 1 d . . .
C7 C 0.4341(2) 0.88397(18) 0.23669(13) 0.0420(5) Uani 1 1 d . . .
H7 H 0.3369 0.8495 0.2381 0.050 Uiso 1 1 calc R . .
C8 C 0.4890(3) 0.97131(19) 0.28587(13) 0.0474(5) Uani 1 1 d . . .
H8 H 0.4342 1.0035 0.3247 0.057 Uiso 1 1 calc R . .
C9 C 0.8518(3) 0.39311(19) 0.07816(14) 0.0513(6) Uani 1 1 d . . .
H9 H 0.8730 0.3161 0.0784 0.062 Uiso 1 1 calc R . .
C10 C 0.8880(2) 0.46080(17) 0.14396(14) 0.0428(5) Uani 1 1 d . . .
H10 H 0.9381 0.4355 0.1947 0.051 Uiso 1 1 calc R . .
C11 C 0.8415(2) 0.57515(16) 0.12783(11) 0.0333(4) Uani 1 1 d . . .
C12 C 0.7687(2) 0.59149(15) 0.04805(11) 0.0322(4) Uani 1 1 d . . .
C13 C 0.6973(2) 0.69250(15) 0.00689(11) 0.0309(4) Uani 1 1 d . . .
C14 C 0.5828(2) 0.76305(15) 0.02905(12) 0.0329(4) Uani 1 1 d . . .
C15 C 0.5389(3) 0.85018(16) -0.02953(14) 0.0449(5) Uani 1 1 d . . .
H15 H 0.4628 0.9046 -0.0239 0.054 Uiso 1 1 calc R . .
C16 C 0.6195(3) 0.84547(19) -0.09433(14) 0.0527(6) Uani 1 1 d . . .
H16 H 0.6053 0.8960 -0.1380 0.063 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.717(3) . ?
S1 C4 1.732(2) . ?
S2 C8 1.706(2) . ?
S2 C5 1.7362(19) . ?
S3 C3 1.760(2) . ?
S3 C11 1.763(2) . ?
S4 C14 1.764(2) . ?
S4 C6 1.7676(19) . ?
S5 C9 1.711(2) . ?
S5 C12 1.7320(19) . ?
S6 C16 1.710(2) . ?
S6 C13 1.7367(19) . ?
C1 C2 1.341(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.433(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C4 C5 1.462(3) . ?
C5 C6 1.377(3) . ?
C6 C7 1.423(3) . ?
C7 C8 1.354(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.346(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.425(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C12 C13 1.463(2) . ?
C13 C14 1.377(3) . ?
C14 C15 1.424(3) . ?
C15 C16 1.357(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
_geom_angle_publ_flag
C1 S1 C4 91.63(12) . . ?
C8 S2 C5 92.04(10) . . ?
C3 S3 C11 103.14(9) . . ?
C14 S4 C6 105.18(9) . . ?
C9 S5 C12 92.27(10) . . ?
C16 S6 C13 92.22(10) . . ?
C2 C1 S1 112.51(17) . . ?
C2 C1 H1 123.7 . . ?
S1 C1 H1 123.7 . . ?
C1 C2 C3 112.5(2) . . ?
C1 C2 H2 123.8 . . ?
C3 C2 H2 123.8 . . ?
C4 C3 C2 112.65(19) . . ?
C4 C3 S3 123.16(15) . . ?
C2 C3 S3 123.78(17) . . ?
C3 C4 C5 128.23(18) . . ?
C3 C4 S1 110.74(14) . . ?
C5 C4 S1 121.00(14) . . ?
C6 C5 C4 129.76(17) . . ?
C6 C5 S2 110.50(14) . . ?
C4 C5 S2 119.53(13) . . ?
C5 C6 C7 112.26(17) . . ?
C5 C6 S4 129.04(14) . . ?
C7 C6 S4 118.67(15) . . ?
C8 C7 C6 113.13(19) . . ?
C8 C7 H7 123.4 . . ?
C6 C7 H7 123.4 . . ?
C7 C8 S2 112.01(16) . . ?
C7 C8 H8 124.0 . . ?
S2 C8 H8 124.0 . . ?
C10 C9 S5 111.98(16) . . ?
C10 C9 H9 124.0 . . ?
S5 C9 H9 124.0 . . ?
C9 C10 C11 113.05(18) . . ?
C9 C10 H10 123.5 . . ?
C11 C10 H10 123.5 . . ?
C12 C11 C10 112.57(17) . . ?
C12 C11 S3 127.90(15) . . ?
C10 C11 S3 119.46(15) . . ?
C11 C12 C13 130.78(17) . . ?
C11 C12 S5 110.11(14) . . ?
C13 C12 S5 119.09(13) . . ?
C14 C13 C12 129.60(18) . . ?
C14 C13 S6 110.29(14) . . ?
C12 C13 S6 120.08(14) . . ?
C13 C14 C15 112.69(18) . . ?
C13 C14 S4 122.84(15) . . ?
C15 C14 S4 124.05(16) . . ?
C16 C15 C14 112.94(19) . . ?
C16 C15 H15 123.5 . . ?
C14 C15 H15 123.5 . . ?
C15 C16 S6 111.87(16) . . ?
C15 C16 H16 124.1 . . ?
S6 C16 H16 124.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C1 C2 0.32(18) . . . . ?
S1 C1 C2 C3 -1.1(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 S3 -171.33(16) . . . . ?
C11 S3 C3 C4 121.56(16) . . . . ?
C11 S3 C3 C2 -66.32(18) . . . . ?
C2 C3 C4 C5 -179.02(18) . . . . ?
S3 C3 C4 C5 -6.1(3) . . . . ?
C2 C3 C4 S1 -1.2(2) . . . . ?
S3 C3 C4 S1 171.66(10) . . . . ?
C1 S1 C4 C3 0.55(15) . . . . ?
C1 S1 C4 C5 178.51(16) . . . . ?
C3 C4 C5 C6 -51.2(3) . . . . ?
S1 C4 C5 C6 131.27(19) . . . . ?
C3 C4 C5 S2 122.99(18) . . . . ?
S1 C4 C5 S2 -54.6(2) . . . . ?
C8 S2 C5 C6 2.23(15) . . . . ?
C8 S2 C5 C4 -172.98(16) . . . . ?
C4 C5 C6 C7 171.97(19) . . . . ?
S2 C5 C6 C7 -2.6(2) . . . . ?
C4 C5 C6 S4 -5.9(3) . . . . ?
S2 C5 C6 S4 179.51(12) . . . . ?
C14 S4 C6 C5 -30.5(2) . . . . ?
C14 S4 C6 C7 151.68(16) . . . . ?
C5 C6 C7 C8 1.7(3) . . . . ?
S4 C6 C7 C8 179.84(15) . . . . ?
C6 C7 C8 S2 0.0(2) . . . . ?
C5 S2 C8 C7 -1.28(18) . . . . ?
C12 S5 C9 C10 -1.08(19) . . . . ?
S5 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 S3 177.66(16) . . . . ?
C3 S3 C11 C12 -36.1(2) . . . . ?
C3 S3 C11 C10 146.90(15) . . . . ?
C10 C11 C12 C13 176.89(19) . . . . ?
S3 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 S5 -1.0(2) . . . . ?
S3 C11 C12 S5 -178.18(12) . . . . ?
C9 S5 C12 C11 1.19(16) . . . . ?
C9 S5 C12 C13 -177.00(16) . . . . ?
C11 C12 C13 C14 -53.6(3) . . . . ?
S5 C12 C13 C14 124.21(19) . . . . ?
C11 C12 C13 S6 128.98(19) . . . . ?
S5 C12 C13 S6 -53.3(2) . . . . ?
C16 S6 C13 C14 -0.33(15) . . . . ?
C16 S6 C13 C12 177.59(16) . . . . ?
C12 C13 C14 C15 -177.24(18) . . . . ?
S6 C13 C14 C15 0.4(2) . . . . ?
C12 C13 C14 S4 -4.4(3) . . . . ?
S6 C13 C14 S4 173.24(10) . . . . ?
C6 S4 C14 C13 116.16(16) . . . . ?
C6 S4 C14 C15 -71.84(17) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
S4 C14 C15 C16 -173.04(16) . . . . ?
C14 C15 C16 S6 0.1(2) . . . . ?
C13 S6 C16 C15 0.15(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.054



