# Electronic Supplementary Material (ESI) for RSC Advances.
# 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).
# 
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# 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 
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data_13RN078_0m
_database_code_depnum_ccdc_archive 'CCDC 1415145'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
11,12-Dimethyl-5-(4-methylbenzenesulfonyl)-2,8,10,13-tetrathia-5-azatricyclo[7.4.0.03,7]trideca-1(9),3,6,11-tetraen
_chemical_name_common            ?
_chemical_melting_point          513
_chemical_formula_moiety         'C17 H15 N O2 S5'
_chemical_formula_sum            'C17 H15 N O2 S5'
_chemical_formula_weight         425.60

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'

_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                   8.9673(14)
_cell_length_b                   9.3214(15)
_cell_length_c                   11.9354(19)
_cell_angle_alpha                107.566(2)
_cell_angle_beta                 103.414(2)
_cell_angle_gamma                92.688(2)
_cell_volume                     917.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8553
_cell_measurement_theta_min      2.3099
_cell_measurement_theta_max      31.3245

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.390
_exptl_absorpt_coefficient_mu    0.643
_shelx_estimated_absorpt_T_min   0.719
_shelx_estimated_absorpt_T_max   0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS V 2.10 (Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker AXS Smart Apex CCD Diffractometer'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10464
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.354
_diffrn_reflns_theta_max         31.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5416
_reflns_number_gt                5133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2012 (Sheldrick, 2012), 
SHELXLE Rev609 (Hübschle et al., 2011)
;
_computing_molecular_graphics    'Mercury (Macrea, 2008)'
_computing_publication_material  
;
        SHELXL97 (Sheldrick, 2008)
;
_refine_special_details          
;
Reflection 0 0 1 was affected by the beam stop and was omitted from the refinement.  
H atoms were positioned geometrically and refined using a riding 
model, with C-H = 0.95 Angstrom with Uiso (H) = 1.2 Ueq (C) for H 
atoms on C(sp2) and 0.98 Angstrom with Uiso (H) = 1.5 Ueq (C) for 
H atoms on C(sp3). In addition, the H atoms of the methyl group 
on TS exibit disorder by a 60 degree rotation with occupancy 
rates refined to 0.67(2) and 0.33(2).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.4251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patt
_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_number_reflns         5416
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
S1 S -0.41568(3) 0.29916(3) 0.15848(2) 0.01286(7) Uani 1 1 d . . . . .
O1 O -0.46048(10) 0.39971(11) 0.25816(8) 0.01871(17) Uani 1 1 d . . . . .
S2 S 0.15909(3) 0.27877(3) 0.43810(2) 0.01354(7) Uani 1 1 d . . . . .
O2 O -0.51634(10) 0.16760(10) 0.07594(9) 0.01989(18) Uani 1 1 d . . . . .
S3 S 0.23837(3) 0.09608(3) 0.60558(2) 0.01361(7) Uani 1 1 d . . . . .
S4 S 0.13780(3) -0.20992(3) 0.38519(2) 0.01299(7) Uani 1 1 d . . . . .
S5 S 0.06568(3) -0.04026(3) 0.20833(2) 0.01376(7) Uani 1 1 d . . . . .
N1 N -0.25808(11) 0.23134(11) 0.22118(9) 0.01315(17) Uani 1 1 d . . . . .
C1 C -0.21374(14) 0.56603(15) -0.04283(11) 0.0193(2) Uani 1 1 d . . . . .
C2 C -0.24854(15) 0.63989(14) 0.06632(12) 0.0202(2) Uani 1 1 d . . . . .
H2 H -0.2280 0.7473 0.0992 0.024 Uiso 1 1 calc R U . . .
C3 C -0.31294(14) 0.55905(13) 0.12824(10) 0.0161(2) Uani 1 1 d . . . . .
H3 H -0.3355 0.6102 0.2031 0.019 Uiso 1 1 calc R U . . .
C4 C -0.34347(12) 0.40266(12) 0.07853(10) 0.01212(19) Uani 1 1 d . . . . .
C5 C -0.31119(16) 0.32524(14) -0.03121(11) 0.0205(2) Uani 1 1 d . . . . .
H5 H -0.3332 0.2179 -0.0645 0.025 Uiso 1 1 calc R U . . .
C6 C -0.24629(17) 0.40823(16) -0.09055(12) 0.0235(3) Uani 1 1 d . . . . .
H6 H -0.2234 0.3568 -0.1652 0.028 Uiso 1 1 calc R U . . .
C7 C -0.14322(17) 0.6532(2) -0.10961(15) 0.0312(3) Uani 1 1 d . . . . .
H7A H -0.1351 0.7623 -0.0670 0.047 Uiso 0.67(2) 1 calc R U P . .
H7B H -0.2087 0.6294 -0.1926 0.047 Uiso 0.67(2) 1 calc R U P . .
H7C H -0.0400 0.6248 -0.1126 0.047 Uiso 0.67(2) 1 calc R U P . .
H7D H -0.1208 0.5820 -0.1812 0.047 Uiso 0.33(2) 1 calc R U P . .
H7E H -0.0472 0.7149 -0.0556 0.047 Uiso 0.33(2) 1 calc R U P . .
H7F H -0.2159 0.7195 -0.1355 0.047 Uiso 0.33(2) 1 calc R U P . .
C8 C -0.14284(13) 0.31769(13) 0.32271(10) 0.01322(19) Uani 1 1 d . . . . .
H8 H -0.1488 0.4141 0.3773 0.016 Uiso 1 1 calc R U . . .
C9 C -0.01909(12) 0.23701(12) 0.32884(10) 0.01207(19) Uani 1 1 d . . . . .
C10 C 0.17129(12) 0.09729(12) 0.45575(10) 0.01181(19) Uani 1 1 d . . . . .
C11 C 0.36046(12) -0.05043(13) 0.58854(10) 0.01341(19) Uani 1 1 d . . . . .
C12 C 0.31812(12) -0.18040(13) 0.49554(10) 0.01342(19) Uani 1 1 d . . . . .
C13 C 0.13062(12) -0.03288(12) 0.36187(10) 0.01193(19) Uani 1 1 d . . . . .
C14 C -0.05923(13) 0.09884(12) 0.22853(10) 0.01227(19) Uani 1 1 d . . . . .
C15 C -0.20700(13) 0.09720(12) 0.16261(10) 0.01324(19) Uani 1 1 d . . . . .
H15 H -0.2635 0.0196 0.0909 0.016 Uiso 1 1 calc R U . . .
C16 C 0.50792(13) -0.01032(15) 0.68857(11) 0.0173(2) Uani 1 1 d . . . . .
H16A H 0.4835 0.0216 0.7677 0.026 Uiso 1 1 calc R U . . .
H16B H 0.5724 0.0727 0.6815 0.026 Uiso 1 1 calc R U . . .
H16C H 0.5639 -0.0991 0.6817 0.026 Uiso 1 1 calc R U . . .
C17 C 0.40921(14) -0.31340(14) 0.47046(12) 0.0189(2) Uani 1 1 d . . . . .
H17A H 0.4905 -0.3048 0.5438 0.028 Uiso 1 1 calc R U . . .
H17B H 0.4562 -0.3138 0.4040 0.028 Uiso 1 1 calc R U . . .
H17C H 0.3400 -0.4080 0.4473 0.028 Uiso 1 1 calc R U . . .


_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 O1 1.4280(9) . ?
S1 O2 1.4295(9) . ?
S1 N1 1.6840(10) . ?
S1 C4 1.7447(11) . ?
S2 C9 1.7532(11) . ?
S2 C10 1.7719(12) . ?
S3 C10 1.7532(11) . ?
S3 C11 1.7836(12) . ?
S4 C13 1.7561(12) . ?
S4 C12 1.7822(12) . ?
S5 C14 1.7512(11) . ?
S5 C13 1.7684(11) . ?
N1 C8 1.3916(14) . ?
N1 C15 1.3916(14) . ?
C1 C2 1.3914(18) . ?
C1 C6 1.396(2) . ?
C1 C7 1.5076(18) . ?
C2 C3 1.3931(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3847(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3947(15) . ?
C5 C6 1.3851(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7D 0.9800 . ?
C7 H7E 0.9800 . ?
C7 H7F 0.9800 . ?
C8 C9 1.3697(15) . ?
C8 H8 0.9500 . ?
C9 C14 1.4309(15) . ?
C10 C13 1.3450(15) . ?
C11 C12 1.3393(16) . ?
C11 C16 1.5052(15) . ?
C12 C17 1.5094(16) . ?
C14 C15 1.3720(15) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
O1 S1 O2 121.47(6) . . ?
O1 S1 N1 105.66(5) . . ?
O2 S1 N1 104.79(5) . . ?
O1 S1 C4 109.84(6) . . ?
O2 S1 C4 110.36(6) . . ?
N1 S1 C4 102.85(5) . . ?
C9 S2 C10 98.25(5) . . ?
C10 S3 C11 102.18(5) . . ?
C13 S4 C12 101.98(5) . . ?
C14 S5 C13 98.01(5) . . ?
C8 N1 C15 110.27(9) . . ?
C8 N1 S1 123.94(8) . . ?
C15 N1 S1 123.98(8) . . ?
C2 C1 C6 118.66(11) . . ?
C2 C1 C7 121.22(13) . . ?
C6 C1 C7 120.11(12) . . ?
C1 C2 C3 121.14(11) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 118.71(11) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.59(11) . . ?
C3 C4 S1 119.22(8) . . ?
C5 C4 S1 119.12(9) . . ?
C6 C5 C4 118.54(11) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 121.35(11) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C7 H7D 109.5 . . ?
H7A C7 H7D 141.1 . . ?
H7B C7 H7D 56.3 . . ?
H7C C7 H7D 56.3 . . ?
C1 C7 H7E 109.5 . . ?
H7A C7 H7E 56.3 . . ?
H7B C7 H7E 141.1 . . ?
H7C C7 H7E 56.3 . . ?
H7D C7 H7E 109.5 . . ?
C1 C7 H7F 109.5 . . ?
H7A C7 H7F 56.3 . . ?
H7B C7 H7F 56.3 . . ?
H7C C7 H7F 141.1 . . ?
H7D C7 H7F 109.5 . . ?
H7E C7 H7F 109.5 . . ?
C9 C8 N1 106.84(10) . . ?
C9 C8 H8 126.6 . . ?
N1 C8 H8 126.6 . . ?
C8 C9 C14 108.04(10) . . ?
C8 C9 S2 129.77(9) . . ?
C14 C9 S2 122.14(8) . . ?
C13 C10 S3 121.06(9) . . ?
C13 C10 S2 123.21(9) . . ?
S3 C10 S2 115.72(6) . . ?
C12 C11 C16 126.22(11) . . ?
C12 C11 S3 121.12(9) . . ?
C16 C11 S3 112.65(8) . . ?
C11 C12 C17 126.68(11) . . ?
C11 C12 S4 120.36(9) . . ?
C17 C12 S4 112.96(9) . . ?
C10 C13 S4 121.29(9) . . ?
C10 C13 S5 123.54(9) . . ?
S4 C13 S5 115.17(6) . . ?
C15 C14 C9 108.20(10) . . ?
C15 C14 S5 129.65(9) . . ?
C9 C14 S5 122.06(8) . . ?
C14 C15 N1 106.64(10) . . ?
C14 C15 H15 126.7 . . ?
N1 C15 H15 126.7 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 S1 N1 C8 -38.29(10) . . . . ?
O2 S1 N1 C8 -167.69(9) . . . . ?
C4 S1 N1 C8 76.89(10) . . . . ?
O1 S1 N1 C15 158.52(9) . . . . ?
O2 S1 N1 C15 29.11(11) . . . . ?
C4 S1 N1 C15 -86.31(10) . . . . ?
C6 C1 C2 C3 0.73(19) . . . . ?
C7 C1 C2 C3 -179.66(12) . . . . ?
C1 C2 C3 C4 -0.60(19) . . . . ?
C2 C3 C4 C5 0.05(18) . . . . ?
C2 C3 C4 S1 177.03(9) . . . . ?
O1 S1 C4 C3 10.95(11) . . . . ?
O2 S1 C4 C3 147.49(9) . . . . ?
N1 S1 C4 C3 -101.17(10) . . . . ?
O1 S1 C4 C5 -172.00(9) . . . . ?
O2 S1 C4 C5 -35.45(11) . . . . ?
N1 S1 C4 C5 75.88(10) . . . . ?
C3 C4 C5 C6 0.35(19) . . . . ?
S1 C4 C5 C6 -176.63(10) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C7 C1 C6 C5 -179.93(13) . . . . ?
C15 N1 C8 C9 -0.57(12) . . . . ?
S1 N1 C8 C9 -165.76(8) . . . . ?
N1 C8 C9 C14 0.35(12) . . . . ?
N1 C8 C9 S2 -177.12(8) . . . . ?
C10 S2 C9 C8 135.09(11) . . . . ?
C10 S2 C9 C14 -42.07(10) . . . . ?
C11 S3 C10 C13 40.96(10) . . . . ?
C11 S3 C10 S2 -139.82(6) . . . . ?
C9 S2 C10 C13 41.20(11) . . . . ?
C9 S2 C10 S3 -138.01(6) . . . . ?
C10 S3 C11 C12 -42.03(10) . . . . ?
C10 S3 C11 C16 138.72(8) . . . . ?
C16 C11 C12 C17 -0.58(18) . . . . ?
S3 C11 C12 C17 -179.72(9) . . . . ?
C16 C11 C12 S4 179.50(9) . . . . ?
S3 C11 C12 S4 0.36(13) . . . . ?
C13 S4 C12 C11 41.93(10) . . . . ?
C13 S4 C12 C17 -138.01(8) . . . . ?
S3 C10 C13 S4 1.73(14) . . . . ?
S2 C10 C13 S4 -177.43(6) . . . . ?
S3 C10 C13 S5 -178.72(6) . . . . ?
S2 C10 C13 S5 2.12(15) . . . . ?
C12 S4 C13 C10 -43.49(10) . . . . ?
C12 S4 C13 S5 136.93(6) . . . . ?
C14 S5 C13 C10 -43.85(11) . . . . ?
C14 S5 C13 S4 135.72(6) . . . . ?
C8 C9 C14 C15 -0.01(13) . . . . ?
S2 C9 C14 C15 177.69(8) . . . . ?
C8 C9 C14 S5 -176.86(8) . . . . ?
S2 C9 C14 S5 0.85(14) . . . . ?
C13 S5 C14 C15 -134.64(11) . . . . ?
C13 S5 C14 C9 41.47(10) . . . . ?
C9 C14 C15 N1 -0.33(12) . . . . ?
S5 C14 C15 N1 176.20(9) . . . . ?
C8 N1 C15 C14 0.56(12) . . . . ?
S1 N1 C15 C14 165.74(8) . . . . ?

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.075



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/cyclohexane'
####################################################################### 
# 
# 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_Apexc15mz070_0m
_database_code_depnum_ccdc_archive 'CCDC 1415146'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2-[4,5-Dimethyl-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole
_chemical_name_common            ?
_chemical_melting_point          487
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N O S4'
_chemical_formula_weight         377.54

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'

_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                   7.8445(19)
_cell_length_b                   8.762(2)
_cell_length_c                   12.265(3)
_cell_angle_alpha                86.427(3)
_cell_angle_beta                 81.337(3)
_cell_angle_gamma                81.142(3)
_cell_volume                     822.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6463
_cell_measurement_theta_min      2.3545
_cell_measurement_theta_max      31.8350

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.34
_exptl_absorpt_coefficient_mu    0.580
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'Apex2 v2013.4-1 (Bruker, 2013)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS APEXII CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20343
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.655
_diffrn_reflns_theta_max         32.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5245
_reflns_number_gt                4731
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 v2013.4-1 (Bruker, 2013)'
_computing_cell_refinement       'SAINT V8.30C (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2014/7 (Sheldrick, 2014), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.2693P] 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_number_reflns         5245
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 -0.35025(13) 0.75735(11) 0.33270(8) 0.01558(17) Uani 1 1 d . . . . .
C2 C -0.20045(13) 0.81652(11) 0.30147(8) 0.01581(17) Uani 1 1 d . . . . .
C3 C -0.76069(14) 0.63359(13) 0.54031(9) 0.0210(2) Uani 1 1 d . . . . .
H3A H -0.8269 0.7328 0.5646 0.032 Uiso 1 1 calc R U . . .
H3B H -0.7017 0.5821 0.6005 0.032 Uiso 1 1 calc R U . . .
H3C H -0.8404 0.5680 0.5197 0.032 Uiso 1 1 calc R U . . .
C4 C -0.62782(13) 0.66097(11) 0.44253(8) 0.01645(18) Uani 1 1 d . . . . .
C5 C -0.62311(13) 0.61866(11) 0.33909(8) 0.01636(18) Uani 1 1 d . . . . .
C6 C -0.74742(15) 0.53173(13) 0.29590(10) 0.0215(2) Uani 1 1 d . . . . .
H6A H -0.8107 0.5988 0.2437 0.032 Uiso 1 1 calc R U . . .
H6B H -0.8305 0.4989 0.3575 0.032 Uiso 1 1 calc R U . . .
H6C H -0.6823 0.4406 0.2583 0.032 Uiso 1 1 calc R U . . .
C7 C 0.19315(13) 1.04781(12) 0.29954(8) 0.01679(18) Uani 1 1 d . . . . .
H7 H 0.2239 1.0887 0.3626 0.020 Uiso 1 1 calc R U . . .
C8 C 0.05919(13) 0.96434(11) 0.29791(8) 0.01561(17) Uani 1 1 d . . . . .
C9 C 0.05947(13) 0.92558(11) 0.18749(8) 0.01494(17) Uani 1 1 d . . . . .
C10 C 0.19364(13) 0.98693(11) 0.12294(8) 0.01569(17) Uani 1 1 d . . . . .
H10 H 0.2247 0.9797 0.0453 0.019 Uiso 1 1 calc R U . . .
C11 C 0.41977(12) 1.14124(11) 0.15978(8) 0.01481(17) Uani 1 1 d . . . . .
C12 C 0.54490(13) 1.13693(11) 0.22922(8) 0.01647(18) Uani 1 1 d . . . . .
H12 H 0.5344 1.0783 0.2971 0.020 Uiso 1 1 calc R U . . .
C13 C 0.68547(13) 1.21762(11) 0.20036(8) 0.01663(18) Uani 1 1 d . . . . .
H13 H 0.7705 1.2144 0.2484 0.020 Uiso 1 1 calc R U . . .
C14 C 0.70113(13) 1.30308(11) 0.10081(8) 0.01570(17) Uani 1 1 d . . . . .
C15 C 0.57606(13) 1.30605(12) 0.03074(8) 0.01820(18) Uani 1 1 d . . . . .
H15 H 0.5873 1.3634 -0.0376 0.022 Uiso 1 1 calc R U . . .
C16 C 0.43561(13) 1.22623(12) 0.05981(8) 0.01767(18) Uani 1 1 d . . . . .
H16 H 0.3505 1.2294 0.0119 0.021 Uiso 1 1 calc R U . . .
C17 C 0.96191(14) 1.38741(13) 0.13557(10) 0.0212(2) Uani 1 1 d . . . . .
H17A H 1.0155 1.2813 0.1514 0.032 Uiso 1 1 calc R U . . .
H17B H 0.9060 1.4349 0.2047 0.032 Uiso 1 1 calc R U . . .
H17C H 1.0519 1.4474 0.0996 0.032 Uiso 1 1 calc R U . . .
N1 N 0.27471(11) 1.06104(10) 0.19225(7) 0.01489(15) Uani 1 1 d . . . . .
O1 O 0.83423(10) 1.38549(9) 0.06424(6) 0.02066(15) Uani 1 1 d . . . . .
S1 S -0.46206(3) 0.76359(3) 0.46765(2) 0.01810(7) Uani 1 1 d . . . . .
S2 S -0.45207(3) 0.67022(3) 0.24071(2) 0.01838(7) Uani 1 1 d . . . . .
S3 S -0.10035(4) 0.90161(3) 0.39741(2) 0.02011(7) Uani 1 1 d . . . . .
S4 S -0.09602(3) 0.81405(3) 0.16340(2) 0.01699(7) 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 1.3504(15) . ?
C1 S2 1.7494(10) . ?
C1 S1 1.7525(11) . ?
C2 S4 1.7666(11) . ?
C2 S3 1.7677(10) . ?
C3 C4 1.4989(14) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.3375(14) . ?
C4 S1 1.7634(11) . ?
C5 C6 1.4988(14) . ?
C5 S2 1.7582(11) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3727(14) . ?
C7 N1 1.3801(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.4163(14) . ?
C8 S3 1.7395(11) . ?
C9 C10 1.3761(14) . ?
C9 S4 1.7441(10) . ?
C10 N1 1.3811(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.3881(14) . ?
C11 C16 1.3936(14) . ?
C11 N1 1.4220(13) . ?
C12 C13 1.3902(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.3913(14) . ?
C13 H13 0.9500 . ?
C14 O1 1.3651(12) . ?
C14 C15 1.3947(14) . ?
C15 C16 1.3849(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O1 1.4282(13) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 S2 122.69(8) . . ?
C2 C1 S1 123.34(8) . . ?
S2 C1 S1 113.96(6) . . ?
C1 C2 S4 121.89(8) . . ?
C1 C2 S3 121.28(8) . . ?
S4 C2 S3 116.83(6) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C3 127.34(9) . . ?
C5 C4 S1 116.99(8) . . ?
C3 C4 S1 115.67(8) . . ?
C4 C5 C6 127.69(10) . . ?
C4 C5 S2 117.01(8) . . ?
C6 C5 S2 115.30(8) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 107.04(9) . . ?
C8 C7 H7 126.5 . . ?
N1 C7 H7 126.5 . . ?
C7 C8 C9 108.11(9) . . ?
C7 C8 S3 134.65(8) . . ?
C9 C8 S3 117.23(7) . . ?
C10 C9 C8 107.73(9) . . ?
C10 C9 S4 135.02(8) . . ?
C8 C9 S4 117.23(7) . . ?
C9 C10 N1 107.09(9) . . ?
C9 C10 H10 126.5 . . ?
N1 C10 H10 126.5 . . ?
C12 C11 C16 119.80(9) . . ?
C12 C11 N1 119.64(9) . . ?
C16 C11 N1 120.54(9) . . ?
C11 C12 C13 120.60(9) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.69(9) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
O1 C14 C13 124.45(9) . . ?
O1 C14 C15 115.95(9) . . ?
C13 C14 C15 119.59(9) . . ?
C16 C15 C14 120.68(9) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.64(9) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 N1 C10 110.02(8) . . ?
C7 N1 C11 124.04(8) . . ?
C10 N1 C11 125.94(8) . . ?
C14 O1 C17 117.10(8) . . ?
C1 S1 C4 95.84(5) . . ?
C1 S2 C5 96.08(5) . . ?
C8 S3 C2 94.25(5) . . ?
C9 S4 C2 94.07(5) . . ?

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
S2 C1 C2 S4 1.19(13) . . . . ?
S1 C1 C2 S4 -177.66(5) . . . . ?
S2 C1 C2 S3 -179.24(5) . . . . ?
S1 C1 C2 S3 1.90(13) . . . . ?
C3 C4 C5 C6 -1.00(18) . . . . ?
S1 C4 C5 C6 -179.80(8) . . . . ?
C3 C4 C5 S2 178.89(8) . . . . ?
S1 C4 C5 S2 0.08(11) . . . . ?
N1 C7 C8 C9 0.17(11) . . . . ?
N1 C7 C8 S3 -179.55(9) . . . . ?
C7 C8 C9 C10 -0.31(11) . . . . ?
S3 C8 C9 C10 179.46(7) . . . . ?
C7 C8 C9 S4 178.34(7) . . . . ?
S3 C8 C9 S4 -1.88(11) . . . . ?
C8 C9 C10 N1 0.33(11) . . . . ?
S4 C9 C10 N1 -177.98(8) . . . . ?
C16 C11 C12 C13 0.47(15) . . . . ?
N1 C11 C12 C13 -178.40(9) . . . . ?
C11 C12 C13 C14 -0.19(15) . . . . ?
C12 C13 C14 O1 -179.55(9) . . . . ?
C12 C13 C14 C15 -0.40(15) . . . . ?
O1 C14 C15 C16 179.94(9) . . . . ?
C13 C14 C15 C16 0.72(15) . . . . ?
C14 C15 C16 C11 -0.44(16) . . . . ?
C12 C11 C16 C15 -0.15(15) . . . . ?
N1 C11 C16 C15 178.70(9) . . . . ?
C8 C7 N1 C10 0.03(11) . . . . ?
C8 C7 N1 C11 179.46(9) . . . . ?
C9 C10 N1 C7 -0.23(11) . . . . ?
C9 C10 N1 C11 -179.64(9) . . . . ?
C12 C11 N1 C7 35.94(14) . . . . ?
C16 C11 N1 C7 -142.92(10) . . . . ?
C12 C11 N1 C10 -144.73(10) . . . . ?
C16 C11 N1 C10 36.41(14) . . . . ?
C13 C14 O1 C17 -2.26(14) . . . . ?
C15 C14 O1 C17 178.56(9) . . . . ?
C2 C1 S1 C4 -177.68(9) . . . . ?
S2 C1 S1 C4 3.37(6) . . . . ?
C5 C4 S1 C1 -2.11(9) . . . . ?
C3 C4 S1 C1 178.94(8) . . . . ?
C2 C1 S2 C5 177.70(9) . . . . ?
S1 C1 S2 C5 -3.34(6) . . . . ?
C4 C5 S2 C1 1.99(9) . . . . ?
C6 C5 S2 C1 -178.10(8) . . . . ?
C7 C8 S3 C2 177.53(11) . . . . ?
C9 C8 S3 C2 -2.17(9) . . . . ?
C1 C2 S3 C8 -174.04(9) . . . . ?
S4 C2 S3 C8 5.55(7) . . . . ?
C10 C9 S4 C2 -177.00(11) . . . . ?
C8 C9 S4 C2 4.81(8) . . . . ?
C1 C2 S4 C9 173.26(9) . . . . ?
S3 C2 S4 C9 -6.32(6) . . . . ?

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.065



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
