# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Concepcio Rovira'
'Ivano Bilotti'
'Fabio Biscarini'
'Francesco Borgatti'
'Aldo Brillante'
'Nuria Crivillers'
'Chiara Dionigi'
'Adina Lazar'
'Michael Leufgen'
'M. Mas-Torrent'
'Silvia Milita'
'Laurens W. Molenkamp'
'Neil Oxtoby'
'Georg Schmidt'
'Raffaele Guido Della Valle'
'Jaume Veciana'
'Elisabetta Venuti'

_publ_contact_author_name        'Dr Concepcio Rovira'
_publ_contact_author_email       CUN@ICMAB.ES

_publ_section_title              
;
THE FOUR POLYMORPHIC MODIFICATIONS OF THE
SEMICONDUCTOR DIBENZO-TETRATHIAFULVALENE
;

# Attachment 'dbttf1g.cif'

data_dbttf1g
_database_code_depnum_ccdc_archive 'CCDC 696271'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 S4'
_chemical_formula_sum            'C14 H8 S4'
_chemical_formula_weight         304.44

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   Cc

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'

_cell_length_a                   15.154(9)
_cell_length_b                   11.571(7)
_cell_length_c                   8.027(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.637(10)
_cell_angle_gamma                90.00
_cell_volume                     1308.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      300(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
_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            9802
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         28.34
_reflns_number_total             3175
_reflns_number_gt                2227
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER shelxtl'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
Check-cif dettects possible addition pseudo symm. In our hands trials to
solve the molecule in higher symmetric group i.e.C2/m were unsuccesfull.
The TOOL ADDSYM implemented in the PLATON facility neither found a higher
symmetry.
An B-alert about the unusual ratio of the maximum and minimum residual
density excursions appears. No myssing atoms were found and the structure
was checked and no disorder was found.
;

_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)+(0.0857P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(16)
_refine_ls_number_reflns         3175
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_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 0.58810(8) 0.48944(8) 0.63434(14) 0.0468(3) Uani 1 1 d . . .
C1 C 0.6656(3) 0.3716(3) 0.7112(5) 0.0393(9) Uani 1 1 d . . .
S2 S 0.62456(8) 0.26073(9) 0.81491(15) 0.0501(4) Uani 1 1 d . . .
C2 C 0.5096(3) 0.3157(3) 0.7592(6) 0.0413(10) Uani 1 1 d . . .
S3 S 0.79439(8) 0.48183(10) 0.60166(15) 0.0549(4) Uani 1 1 d . . .
C3 C 0.4373(4) 0.2599(4) 0.7952(8) 0.0493(16) Uani 1 1 d . . .
H3A H 0.4483 0.1888 0.8533 0.059 Uiso 1 1 calc R . .
S4 S 0.82923(8) 0.25006(9) 0.77341(15) 0.0543(4) Uani 1 1 d . . .
C4 C 0.3489(4) 0.3114(5) 0.7434(8) 0.0687(15) Uani 1 1 d . . .
H4A H 0.3001 0.2736 0.7653 0.082 Uiso 1 1 calc R . .
C5 C 0.3313(4) 0.4190(5) 0.6592(7) 0.0632(14) Uani 1 1 d . . .
H5A H 0.2715 0.4523 0.6260 0.076 Uiso 1 1 calc R . .
C6 C 0.4026(4) 0.4756(5) 0.6254(8) 0.0512(17) Uani 1 1 d . . .
H6A H 0.3909 0.5479 0.5711 0.061 Uiso 1 1 calc R . .
C7 C 0.4924(3) 0.4255(3) 0.6719(6) 0.0398(9) Uani 1 1 d . . .
C8 C 0.7510(3) 0.3689(3) 0.6961(5) 0.0394(9) Uani 1 1 d . . .
C9 C 0.9095(3) 0.4264(4) 0.6640(6) 0.0398(9) Uani 1 1 d . . .
C10 C 0.9821(4) 0.4852(5) 0.6360(8) 0.059(2) Uani 1 1 d . . .
H10A H 0.9703 0.5572 0.5808 0.071 Uiso 1 1 calc R . .
C11 C 1.0711(4) 0.4388(5) 0.6882(9) 0.0738(16) Uani 1 1 d . . .
H11A H 1.1202 0.4790 0.6709 0.089 Uiso 1 1 calc R . .
C12 C 1.0873(4) 0.3258(5) 0.7710(8) 0.0732(17) Uani 1 1 d . . .
H12A H 1.1473 0.2925 0.8081 0.088 Uiso 1 1 calc R . .
C13 C 1.0137(5) 0.2679(5) 0.7947(9) 0.0579(18) Uani 1 1 d . . .
H13A H 1.0240 0.1950 0.8471 0.070 Uiso 1 1 calc R . .
C14 C 0.9255(3) 0.3165(4) 0.7421(6) 0.0438(10) Uani 1 1 d . . .

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 0.0447(7) 0.0368(5) 0.0604(8) 0.0090(5) 0.0213(6) 0.0069(4)
C1 0.040(2) 0.0314(19) 0.044(3) 0.0010(17) 0.0133(18) 0.0017(15)
S2 0.0424(8) 0.0417(6) 0.0681(9) 0.0164(5) 0.0226(6) 0.0029(4)
C2 0.038(2) 0.041(2) 0.045(3) -0.0051(18) 0.016(2) 0.0008(18)
S3 0.0502(9) 0.0458(6) 0.0749(10) 0.0232(6) 0.0303(7) 0.0092(5)
C3 0.047(4) 0.051(3) 0.056(3) -0.002(2) 0.026(3) -0.0056(19)
S4 0.0527(9) 0.0402(6) 0.0789(10) 0.0208(5) 0.0346(7) 0.0115(5)
C4 0.047(3) 0.099(4) 0.070(4) -0.026(3) 0.034(3) -0.007(3)
C5 0.047(3) 0.081(4) 0.070(4) -0.012(3) 0.031(3) 0.007(3)
C6 0.041(4) 0.054(3) 0.057(4) -0.013(2) 0.016(3) 0.006(2)
C7 0.039(2) 0.042(2) 0.040(2) -0.0046(18) 0.0165(18) 0.0004(17)
C8 0.042(2) 0.0316(19) 0.047(3) 0.0066(16) 0.0195(19) 0.0049(15)
C9 0.046(3) 0.041(2) 0.037(2) -0.0002(17) 0.0199(19) 0.0028(18)
C10 0.068(5) 0.056(3) 0.068(4) -0.003(2) 0.042(4) -0.006(2)
C11 0.059(4) 0.072(3) 0.106(5) -0.010(3) 0.049(3) -0.008(3)
C12 0.044(3) 0.087(4) 0.091(5) 0.000(3) 0.027(3) 0.013(3)
C13 0.054(5) 0.062(3) 0.061(4) 0.008(2) 0.025(3) 0.017(2)
C14 0.043(3) 0.046(2) 0.045(3) 0.0008(19) 0.019(2) 0.0032(19)

_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 C7 1.750(5) . ?
S1 C1 1.756(4) . ?
C1 C8 1.344(4) . ?
C1 S2 1.763(4) . ?
S2 C2 1.751(5) . ?
C2 C3 1.391(7) . ?
C2 C7 1.428(6) . ?
S3 C9 1.749(5) . ?
S3 C8 1.756(4) . ?
C3 C4 1.384(8) . ?
S4 C14 1.747(5) . ?
S4 C8 1.772(4) . ?
C4 C5 1.394(9) . ?
C5 C6 1.372(8) . ?
C6 C7 1.398(7) . ?
C9 C10 1.381(7) . ?
C9 C14 1.400(6) . ?
C10 C11 1.365(8) . ?
C11 C12 1.446(9) . ?
C12 C13 1.374(8) . ?
C13 C14 1.365(7) . ?

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
C7 S1 C1 95.8(2) . . ?
C8 C1 S1 121.9(3) . . ?
C8 C1 S2 123.0(3) . . ?
S1 C1 S2 115.1(2) . . ?
C2 S2 C1 96.1(2) . . ?
C3 C2 C7 120.0(4) . . ?
C3 C2 S2 124.3(4) . . ?
C7 C2 S2 115.6(3) . . ?
C9 S3 C8 95.6(2) . . ?
C4 C3 C2 119.1(5) . . ?
C14 S4 C8 95.4(2) . . ?
C3 C4 C5 121.4(5) . . ?
C6 C5 C4 119.9(5) . . ?
C5 C6 C7 120.6(6) . . ?
C6 C7 C2 118.9(4) . . ?
C6 C7 S1 124.5(4) . . ?
C2 C7 S1 116.6(3) . . ?
C1 C8 S3 123.2(3) . . ?
C1 C8 S4 121.9(3) . . ?
S3 C8 S4 114.8(2) . . ?
C10 C9 C14 120.2(4) . . ?
C10 C9 S3 123.0(4) . . ?
C14 C9 S3 116.8(3) . . ?
C11 C10 C9 120.9(5) . . ?
C10 C11 C12 118.5(5) . . ?
C13 C12 C11 119.7(5) . . ?
C14 C13 C12 120.6(5) . . ?
C13 C14 C9 120.1(4) . . ?
C13 C14 S4 123.2(4) . . ?
C9 C14 S4 116.6(3) . . ?

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
C7 S1 C1 C8 173.2(3) . . . . ?
C7 S1 C1 S2 -8.7(3) . . . . ?
C8 C1 S2 C2 -173.4(3) . . . . ?
S1 C1 S2 C2 8.6(3) . . . . ?
C1 S2 C2 C3 175.3(4) . . . . ?
C1 S2 C2 C7 -4.9(3) . . . . ?
C7 C2 C3 C4 0.8(7) . . . . ?
S2 C2 C3 C4 -179.5(4) . . . . ?
C2 C3 C4 C5 -1.2(8) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C4 C5 C6 C7 1.1(8) . . . . ?
C5 C6 C7 C2 -1.6(7) . . . . ?
C5 C6 C7 S1 179.7(4) . . . . ?
C3 C2 C7 C6 0.6(7) . . . . ?
S2 C2 C7 C6 -179.2(3) . . . . ?
C3 C2 C7 S1 179.4(3) . . . . ?
S2 C2 C7 S1 -0.3(4) . . . . ?
C1 S1 C7 C6 -175.8(4) . . . . ?
C1 S1 C7 C2 5.4(4) . . . . ?
S1 C1 C8 S3 0.7(4) . . . . ?
S2 C1 C8 S3 -177.1(3) . . . . ?
S1 C1 C8 S4 -180.0(3) . . . . ?
S2 C1 C8 S4 2.2(4) . . . . ?
C9 S3 C8 C1 170.7(3) . . . . ?
C9 S3 C8 S4 -8.6(3) . . . . ?
C14 S4 C8 C1 -171.5(3) . . . . ?
C14 S4 C8 S3 7.9(3) . . . . ?
C8 S3 C9 C10 -175.0(4) . . . . ?
C8 S3 C9 C14 6.3(4) . . . . ?
C14 C9 C10 C11 -1.8(8) . . . . ?
S3 C9 C10 C11 179.5(4) . . . . ?
C9 C10 C11 C12 1.0(8) . . . . ?
C10 C11 C12 C13 0.2(9) . . . . ?
C11 C12 C13 C14 -0.5(9) . . . . ?
C12 C13 C14 C9 -0.3(8) . . . . ?
C12 C13 C14 S4 -178.1(5) . . . . ?
C10 C9 C14 C13 1.5(7) . . . . ?
S3 C9 C14 C13 -179.7(4) . . . . ?
C10 C9 C14 S4 179.5(3) . . . . ?
S3 C9 C14 S4 -1.8(5) . . . . ?
C8 S4 C14 C13 174.2(4) . . . . ?
C8 S4 C14 C9 -3.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.315
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.093


