# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_DTQ_open_0ma
_database_code_depnum_ccdc_archive 'CCDC 1508336'
_audit_update_record             
;
2016-10-05 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2,3-Bis(2,5-dimethylthiophen-3-yl)-5,6-dimethylbenzoquinone 
;
_chemical_name_common            DTQopen
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 O2 S2'
_chemical_formula_weight         356.48

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'
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'

_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                   8.8493(14)
_cell_length_b                   11.2288(18)
_cell_length_c                   18.574(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.450(2)
_cell_angle_gamma                90.00
_cell_volume                     1845.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4704
_cell_measurement_theta_min      2.847
_cell_measurement_theta_max      27.548

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   'program SADABS ver. 2.03(Sheldrick)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10339
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4245
_reflns_number_gt                3205
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEXII (Bruker AXS, 2006)'
_computing_cell_refinement       'APEXII (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL ver. 6.31'
_computing_publication_material  'Bruker XSHELL ver. 6.31'

_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)+(0.1000P)²+0.4875P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4245
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1500
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_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
C1 C -0.1449(4) 0.2015(4) 0.05658(16) 0.0964(9) Uani 1 1 d . . .
C2 C -0.0348(2) 0.1616(2) 0.11365(11) 0.0699(6) Uani 1 1 d . . .
C3 C 0.2428(4) -0.0536(3) 0.2198(2) 0.0886(8) Uani 1 1 d . . .
C4 C 0.1426(2) 0.04307(18) 0.19139(12) 0.0643(5) Uani 1 1 d . . .
C5 C 0.1231(2) 0.15735(16) 0.21516(10) 0.0542(4) Uani 1 1 d . . .
C6 C 0.0233(2) 0.2249(2) 0.16991(10) 0.0593(5) Uani 1 1 d . . .
C7 C 0.18773(18) 0.20556(16) 0.28308(10) 0.0505(4) Uani 1 1 d . . .
C8 C 0.27192(18) 0.30607(15) 0.28716(9) 0.0480(4) Uani 1 1 d . . .
C9 C 0.32747(19) 0.37169(15) 0.22311(9) 0.0497(4) Uani 1 1 d . . .
C10 C 0.2787(2) 0.48876(16) 0.20325(11) 0.0566(4) Uani 1 1 d . . .
C11 C 0.3525(2) 0.53336(17) 0.14554(11) 0.0615(5) Uani 1 1 d . . .
C12 C 0.3277(4) 0.6503(2) 0.10807(18) 0.0853(8) Uani 1 1 d . . .
C13 C 0.4396(2) 0.32959(17) 0.18047(10) 0.0570(4) Uani 1 1 d . . .
C14 C 0.5224(3) 0.2135(2) 0.18529(16) 0.0781(7) Uani 1 1 d . . .
C15 C 0.3197(2) 0.35406(15) 0.35826(10) 0.0526(4) Uani 1 1 d . . .
C16 C 0.2831(2) 0.28860(17) 0.42551(10) 0.0559(4) Uani 1 1 d . . .
C17 C 0.2041(2) 0.18697(17) 0.42171(10) 0.0574(4) Uani 1 1 d . . .
C18 C 0.1485(2) 0.14240(17) 0.35145(11) 0.0579(4) Uani 1 1 d . . .
C19 C 0.1645(4) 0.1114(3) 0.48545(16) 0.0834(7) Uani 1 1 d . . .
C20 C 0.3436(4) 0.3428(3) 0.49384(14) 0.0822(7) Uani 1 1 d . . .
H1 H 0.303(4) 0.307(3) 0.5328(19) 0.120(11) Uiso 1 1 d . . .
H2 H 0.440(5) 0.357(4) 0.496(2) 0.149(16) Uiso 1 1 d . . .
H3 H 0.310(5) 0.427(4) 0.500(2) 0.151(15) Uiso 1 1 d . . .
H4 H 0.171(4) 0.142(3) 0.531(2) 0.131(13) Uiso 1 1 d . . .
H5 H 0.210(5) 0.033(4) 0.479(2) 0.143(15) Uiso 1 1 d . . .
H6 H 0.064(5) 0.091(4) 0.488(2) 0.138(13) Uiso 1 1 d . . .
H7 H 0.230(5) 0.678(3) 0.118(2) 0.133(14) Uiso 1 1 d . . .
H8 H 0.402(4) 0.710(4) 0.118(2) 0.140(13) Uiso 1 1 d . . .
H9 H 0.325(4) 0.641(3) 0.061(2) 0.125(13) Uiso 1 1 d . . .
H10 H 0.637(4) 0.225(3) 0.1825(19) 0.128(11) Uiso 1 1 d . . .
H11 H 0.501(4) 0.173(3) 0.2312(18) 0.109(9) Uiso 1 1 d . . .
H12 H 0.475(4) 0.153(3) 0.156(2) 0.136(13) Uiso 1 1 d . . .
H13 H 0.192(2) 0.5432(17) 0.2318(10) 0.052(5) Uiso 1 1 d . . .
H14 H -0.101(4) 0.206(3) 0.007(2) 0.131(12) Uiso 1 1 d . . .
H15 H -0.166(4) 0.283(4) 0.064(2) 0.135(14) Uiso 1 1 d . . .
H16 H -0.241(5) 0.158(4) 0.056(2) 0.167(17) Uiso 1 1 d . . .
H17 H 0.329(5) -0.068(4) 0.185(2) 0.151(15) Uiso 1 1 d . . .
H18 H 0.298(5) -0.029(4) 0.264(2) 0.141(14) Uiso 1 1 d . . .
H19 H 0.187(4) -0.124(4) 0.224(2) 0.142(13) Uiso 1 1 d . . .
H20 H -0.001(2) 0.3103(19) 0.1805(10) 0.051(5) Uiso 1 1 d . . .
O1 O 0.0684(2) 0.05297(16) 0.34933(10) 0.0899(6) Uani 1 1 d . . .
O2 O 0.3925(2) 0.44562(14) 0.36169(9) 0.0788(5) Uani 1 1 d . . .
S1 S 0.48563(7) 0.43370(5) 0.11577(3) 0.0699(2) Uani 1 1 d . . .
S2 S 0.03519(7) 0.01904(6) 0.11460(3) 0.0767(2) 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 1.502(4) . ?
C2 C6 1.361(3) . ?
C2 S2 1.717(3) . ?
C3 C4 1.495(4) . ?
C4 C5 1.368(3) . ?
C4 S2 1.729(2) . ?
C5 C6 1.432(3) . ?
C5 C7 1.483(3) . ?
C7 C8 1.354(2) . ?
C7 C18 1.498(3) . ?
C8 C15 1.485(3) . ?
C8 C9 1.486(2) . ?
C9 C13 1.359(3) . ?
C9 C10 1.431(3) . ?
C10 C11 1.355(3) . ?
C11 C12 1.502(3) . ?
C11 S1 1.719(2) . ?
C13 C14 1.498(3) . ?
C13 S1 1.7275(19) . ?
C15 O2 1.214(2) . ?
C15 C16 1.488(3) . ?
C16 C17 1.340(3) . ?
C16 C20 1.503(3) . ?
C17 C18 1.478(3) . ?
C17 C19 1.501(3) . ?
C18 O1 1.229(2) . ?

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
C6 C2 C1 128.7(3) . . ?
C6 C2 S2 110.18(17) . . ?
C1 C2 S2 121.1(2) . . ?
C5 C4 C3 130.0(2) . . ?
C5 C4 S2 110.04(16) . . ?
C3 C4 S2 119.89(19) . . ?
C4 C5 C6 112.71(18) . . ?
C4 C5 C7 124.61(18) . . ?
C6 C5 C7 122.54(17) . . ?
C2 C6 C5 113.7(2) . . ?
C8 C7 C5 124.06(16) . . ?
C8 C7 C18 118.57(16) . . ?
C5 C7 C18 117.25(15) . . ?
C7 C8 C15 120.34(16) . . ?
C7 C8 C9 123.61(16) . . ?
C15 C8 C9 116.00(14) . . ?
C13 C9 C10 112.90(16) . . ?
C13 C9 C8 122.79(16) . . ?
C10 C9 C8 124.11(16) . . ?
C11 C10 C9 113.40(18) . . ?
C10 C11 C12 128.3(2) . . ?
C10 C11 S1 110.45(14) . . ?
C12 C11 S1 121.2(2) . . ?
C9 C13 C14 128.83(18) . . ?
C9 C13 S1 110.32(14) . . ?
C14 C13 S1 120.82(16) . . ?
O2 C15 C8 120.08(17) . . ?
O2 C15 C16 119.56(17) . . ?
C8 C15 C16 120.34(15) . . ?
C17 C16 C15 119.59(17) . . ?
C17 C16 C20 124.9(2) . . ?
C15 C16 C20 115.48(19) . . ?
C16 C17 C18 120.32(17) . . ?
C16 C17 C19 124.4(2) . . ?
C18 C17 C19 115.26(19) . . ?
O1 C18 C17 119.50(18) . . ?
O1 C18 C7 119.80(18) . . ?
C17 C18 C7 120.69(15) . . ?
C11 S1 C13 92.91(9) . . ?
C2 S2 C4 93.38(10) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.040
