# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_twin5
_database_code_depnum_ccdc_archive 'CCDC 1405235'
_audit_update_record             
;
2015-06-06 deposited with the CCDC.
2015-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        PyDTI-C8
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H36 N2 S4'
_chemical_formula_weight         504.81

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.5302(2)
_cell_length_b                   10.3934(5)
_cell_length_c                   14.1186(6)
_cell_angle_alpha                81.405(2)
_cell_angle_beta                 86.591(2)
_cell_angle_gamma                82.721(2)
_cell_volume                     651.44(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4100
_cell_measurement_theta_min      2.6368
_cell_measurement_theta_max      26.0013

_exptl_crystal_description       Columnar
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             270
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.382
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7810
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            2650
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.996
_diffrn_reflns_theta_max         26.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2650
_reflns_number_gt                2279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+0.1606P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2650
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1880(4) -0.01309(16) 0.42214(11) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.9841(4) 0.09855(15) 0.41614(11) 0.0164(4) Uani 1 1 d . . . . .
H2 H 0.9732 0.1633 0.3609 0.020 Uiso 1 1 calc R U . . .
C3 C 0.7973(4) 0.10890(15) 0.49650(11) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.5594(4) 0.21301(16) 0.51482(11) 0.0174(4) Uani 1 1 d . . . . .
C5 C 0.2116(4) 0.25647(17) 0.65484(12) 0.0204(4) Uani 1 1 d . . . . .
H5A H 0.0901 0.2001 0.6999 0.025 Uiso 1 1 calc R U . . .
H5B H 0.0780 0.3099 0.6071 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3538(4) 0.34601(16) 0.70942(12) 0.0194(4) Uani 1 1 d . . . . .
H6A H 0.4889 0.3962 0.6648 0.023 Uiso 1 1 calc R U . . .
H6B H 0.4758 0.2917 0.7599 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1285(4) 0.44156(17) 0.75561(12) 0.0198(4) Uani 1 1 d . . . . .
H7A H 0.0166 0.5006 0.7048 0.024 Uiso 1 1 calc R U . . .
H7B H -0.0156 0.3920 0.7968 0.024 Uiso 1 1 calc R U . . .
C8 C 0.2745(4) 0.52336(17) 0.81570(12) 0.0195(4) Uani 1 1 d . . . . .
H8A H 0.4093 0.5766 0.7734 0.023 Uiso 1 1 calc R U . . .
H8B H 0.3980 0.4637 0.8632 0.023 Uiso 1 1 calc R U . . .
C9 C 0.0568(4) 0.61429(17) 0.86855(12) 0.0199(4) Uani 1 1 d . . . . .
H9A H -0.0602 0.6772 0.8211 0.024 Uiso 1 1 calc R U . . .
H9B H -0.0838 0.5619 0.9090 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2096(4) 0.68995(16) 0.93129(12) 0.0197(4) Uani 1 1 d . . . . .
H10A H 0.3416 0.7459 0.8901 0.024 Uiso 1 1 calc R U . . .
H10B H 0.3364 0.6269 0.9759 0.024 Uiso 1 1 calc R U . . .
C11 C -0.0036(4) 0.77583(17) 0.98940(12) 0.0232(4) Uani 1 1 d . . . . .
H11A H -0.1402 0.7207 1.0292 0.028 Uiso 1 1 calc R U . . .
H11B H -0.1253 0.8414 0.9450 0.028 Uiso 1 1 calc R U . . .
C12 C 0.1550(4) 0.84679(18) 1.05415(13) 0.0275(4) Uani 1 1 d . . . . .
H12A H 0.2828 0.7827 1.0965 0.041 Uiso 1 1 calc R U . . .
H12B H 0.0073 0.8958 1.0929 0.041 Uiso 1 1 calc R U . . .
H12C H 0.2771 0.9076 1.0148 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5841(4) 0.05562(16) 0.64915(12) 0.0177(4) Uani 1 1 d . . . . .
S1 S 0.45376(11) 0.34823(4) 0.44448(3) 0.02562(13) Uani 1 1 d . . . . .
S2 S 0.51271(11) -0.01858(4) 0.75643(3) 0.02571(14) Uani 1 1 d . . . . .
N1 N 0.4396(3) 0.17416(13) 0.60585(9) 0.0173(3) Uani 1 1 d . . . . .


_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
C1 C2 1.384(2) . ?
C1 C3 1.402(2) 2_756 ?
C1 C13 1.472(2) 2_756 ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C1 1.402(2) 2_756 ?
C3 C4 1.468(2) . ?
C4 N1 1.388(2) . ?
C4 S1 1.6307(16) . ?
C5 N1 1.465(2) . ?
C5 C6 1.517(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.520(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.518(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.517(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.519(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.392(2) . ?
C13 C1 1.472(2) 2_756 ?
C13 S2 1.6277(17) . ?

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
C2 C1 C3 122.40(15) . 2_756 ?
C2 C1 C13 129.52(14) . 2_756 ?
C3 C1 C13 108.08(14) 2_756 2_756 ?
C3 C2 C1 115.05(14) . . ?
C3 C2 H2 122.5 . . ?
C1 C2 H2 122.5 . . ?
C2 C3 C1 122.55(15) . 2_756 ?
C2 C3 C4 129.56(15) . . ?
C1 C3 C4 107.90(14) 2_756 . ?
N1 C4 C3 106.04(13) . . ?
N1 C4 S1 126.01(12) . . ?
C3 C4 S1 127.95(13) . . ?
N1 C5 C6 110.71(13) . . ?
N1 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 113.34(13) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 112.38(14) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 114.34(14) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 112.90(14) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 114.06(14) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 112.96(15) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C1 105.58(13) . 2_756 ?
N1 C13 S2 126.52(13) . . ?
C1 C13 S2 127.90(12) 2_756 . ?
C4 N1 C13 112.38(13) . . ?
C4 N1 C5 123.41(13) . . ?
C13 N1 C5 123.82(13) . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6



_exptl_crystal_recrystallization_method 'solvent diffusion'
