# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_TSTF_dmd15pt5_x
_database_code_depnum_ccdc_archive 'CCDC 1501343'
_audit_update_record             
;
2016-08-29 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H4 S Se3'
_chemical_formula_weight         345.03

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'
Se Se -0.0929 2.2259 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

_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                   8.1836(2)
_cell_length_b                   8.4919(2)
_cell_length_c                   13.1439(3)
_cell_angle_alpha                101.046(2)
_cell_angle_beta                 99.302(2)
_cell_angle_gamma                96.025(2)
_cell_volume                     875.96(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    13612
_cell_measurement_theta_min      3.2110
_cell_measurement_theta_max      33.3760

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.616
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    12.756
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  CrysAlisPro, Agilent Technologies,
  Version 1.171.37.35
  Empirical absorption correction using spherical 
  harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_crystal_treatment        
;
attached with Exxon Paratone N to a nylon loop and quenched 
in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. 
;


_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number            41916
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_max         35.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7408
_reflns_number_gt                5350
_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       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_cell_refinement       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_data_reduction        
;
  CrysAlisPro, Agilent Technologies,
;

_computing_structure_solution    'ShelxT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPIII  (Burnett, N.M., Johnson,C.K., 1996). 
  WinGX (Farrugia, 1999)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_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)+(0.04P)²+0.5P] 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         7408
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Se1_1 Se 0.26559(4) 0.11335(4) 0.44605(2) 0.03392(8) Uani 0.84 1 d . . P . .
S1_1 S 0.26559(4) 0.11335(4) 0.44605(2) 0.03392(8) Uani 0.16 1 d . . P . .
Se2_1 Se 0.44002(5) 0.06303(4) 0.66724(3) 0.03331(8) Uani 0.66 1 d . . P . .
S2_1 S 0.44002(5) 0.06303(4) 0.66724(3) 0.03331(8) Uani 0.34 1 d . . P . .
C1_1 C 0.4410(3) 0.0337(3) 0.52254(18) 0.0227(4) Uani 1 1 d . . . . .
C2_1 C 0.1629(4) 0.1576(4) 0.5617(2) 0.0362(6) Uani 1 1 d . . . . .
H2_1 H 0.0577 0.1961 0.5551 0.043 Uiso 1 1 calc R U . . .
C3_1 C 0.2376(4) 0.1351(4) 0.6539(2) 0.0372(6) Uani 1 1 d . . . . .
H3_1 H 0.1850 0.1567 0.7135 0.045 Uiso 1 1 calc R U . . .
Se1_2 Se 0.26718(4) 0.62597(5) 0.50623(3) 0.04183(9) Uani 0.8 1 d . . P . .
S1_2 S 0.26718(4) 0.62597(5) 0.50623(3) 0.04183(9) Uani 0.2 1 d . . P . .
Se2_2 Se 0.00710(4) 0.37948(5) 0.32981(3) 0.03722(9) Uani 0.7 1 d . . P . .
S2_2 S 0.00710(4) 0.37948(5) 0.32981(3) 0.03722(9) Uani 0.3 1 d . . P . .
C1_2 C 0.0552(3) 0.5000(3) 0.46749(19) 0.0235(5) Uani 1 1 d . . . . .
C2_2 C 0.3257(4) 0.5465(3) 0.3789(2) 0.0350(6) Uani 1 1 d . . . . .
H2_2 H 0.4341 0.5796 0.3667 0.042 Uiso 1 1 calc R U . . .
C3_2 C 0.2170(4) 0.4437(3) 0.3045(2) 0.0330(6) Uani 1 1 d . . . . .
H3_2 H 0.2464 0.4028 0.2384 0.040 Uiso 1 1 calc R U . . .
Se1_3 Se 0.37347(5) 0.23654(4) -0.02323(3) 0.04085(9) Uani 0.8 1 d . . P . .
S1_3 S 0.37347(5) 0.23654(4) -0.02323(3) 0.04085(9) Uani 0.2 1 d . . P . .
Se2_3 Se 0.61494(5) 0.47860(4) 0.16699(3) 0.03741(9) Uani 0.7 1 d . . P . .
S2_3 S 0.61494(5) 0.47860(4) 0.16699(3) 0.03741(9) Uani 0.3 1 d . . P . .
C1_3 C 0.4975(3) 0.4430(3) 0.0289(2) 0.0245(5) Uani 1 1 d . . . . .
C2_3 C 0.4451(4) 0.1688(4) 0.1003(3) 0.0371(6) Uani 1 1 d . . . . .
H2_3 H 0.4096 0.0614 0.1065 0.044 Uiso 1 1 calc R U . . .
C3_3 C 0.5452(4) 0.2701(4) 0.1791(2) 0.0363(6) Uani 1 1 d . . . . .
H3_3 H 0.5820 0.2360 0.2427 0.044 Uiso 1 1 calc R U . . .
Se1_4 Se 0.10381(4) 0.75953(4) -0.04426(3) 0.03625(8) Uani 0.8 1 d . . P . .
S1_4 S 0.10381(4) 0.75953(4) -0.04426(3) 0.03625(8) Uani 0.2 1 d . . P . .
Se2_4 Se 0.05992(5) 0.97086(4) 0.17140(3) 0.03369(8) Uani 0.7 1 d . . P . .
S2_4 S 0.05992(5) 0.97086(4) 0.17140(3) 0.03369(8) Uani 0.3 1 d . . P . .
C1_4 C 0.0311(3) 0.9457(3) 0.02533(19) 0.0238(4) Uani 1 1 d . . . . .
C2_4 C 0.1477(4) 0.6825(4) 0.0774(3) 0.0403(7) Uani 1 1 d . . . . .
H2_4 H 0.1831 0.5791 0.0752 0.048 Uiso 1 1 calc R U . . .
C3_4 C 0.1297(4) 0.7717(4) 0.1680(2) 0.0391(7) Uani 1 1 d . . . . .
H3_4 H 0.1528 0.7328 0.2312 0.047 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
Se1_1 C2_1 1.849(3) . ?
Se1_1 C1_1 1.878(2) . ?
Se2_1 C1_1 1.872(2) . ?
C1_1 C1_1 1.335(5) 2_656 ?
C2_1 C3_1 1.323(4) . ?
C2_1 H2_1 0.9500 . ?
C3_1 H3_1 0.9500 . ?
Se1_2 C2_2 1.838(3) . ?
Se1_2 C1_2 1.878(2) . ?
Se2_2 C1_2 1.858(2) . ?
C1_2 C1_2 1.341(5) 2_566 ?
C2_2 C3_2 1.318(4) . ?
C2_2 H2_2 0.9500 . ?
C3_2 H3_2 0.9500 . ?
Se1_3 C2_3 1.852(3) . ?
Se1_3 C1_3 1.875(2) . ?
Se2_3 C1_3 1.864(3) . ?
C1_3 C1_3 1.342(5) 2_665 ?
C2_3 C3_3 1.312(4) . ?
C2_3 H2_3 0.9500 . ?
C3_3 H3_3 0.9500 . ?
Se1_4 C2_4 1.838(3) . ?
Se1_4 C1_4 1.874(2) . ?
Se2_4 C1_4 1.864(2) . ?
C1_4 C1_4 1.333(5) 2_575 ?
C2_4 C3_4 1.322(4) . ?
C2_4 H2_4 0.9500 . ?
C3_4 H3_4 0.9500 . ?

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_1 Se1_1 C1_1 92.29(12) . . ?
C1_1 C1_1 Se2_1 123.1(2) 2_656 . ?
C1_1 C1_1 Se1_1 122.5(2) 2_656 . ?
Se2_1 C1_1 Se1_1 114.42(12) . . ?
C3_1 C2_1 Se1_1 119.4(2) . . ?
C3_1 C2_1 H2_1 120.3 . . ?
Se1_1 C2_1 H2_1 120.3 . . ?
C2_1 C3_1 H3_1 119.8 . . ?
C2_2 Se1_2 C1_2 92.74(12) . . ?
C1_2 C1_2 Se2_2 122.3(2) 2_566 . ?
C1_2 C1_2 Se1_2 123.0(2) 2_566 . ?
Se2_2 C1_2 Se1_2 114.70(13) . . ?
C3_2 C2_2 Se1_2 119.9(2) . . ?
C3_2 C2_2 H2_2 120.0 . . ?
Se1_2 C2_2 H2_2 120.0 . . ?
C2_2 C3_2 H3_2 120.2 . . ?
C2_3 Se1_3 C1_3 92.44(12) . . ?
C1_3 C1_3 Se2_3 122.2(3) 2_665 . ?
C1_3 C1_3 Se1_3 122.6(3) 2_665 . ?
Se2_3 C1_3 Se1_3 115.20(13) . . ?
C3_3 C2_3 Se1_3 119.6(2) . . ?
C3_3 C2_3 H2_3 120.2 . . ?
Se1_3 C2_3 H2_3 120.2 . . ?
C2_3 C3_3 H3_3 119.9 . . ?
C2_4 Se1_4 C1_4 92.57(12) . . ?
C1_4 C1_4 Se2_4 122.7(2) 2_575 . ?
C1_4 C1_4 Se1_4 122.6(2) 2_575 . ?
Se2_4 C1_4 Se1_4 114.68(13) . . ?
C3_4 C2_4 Se1_4 119.7(2) . . ?
C3_4 C2_4 H2_4 120.1 . . ?
Se1_4 C2_4 H2_4 120.1 . . ?
C2_4 C3_4 H3_4 120.1 . . ?

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
C2_1 Se1_1 C1_1 C1_1 174.5(3) . . . 2_656 ?
C2_1 Se1_1 C1_1 Se2_1 -7.43(15) . . . . ?
C1_1 Se1_1 C2_1 C3_1 4.3(3) . . . . ?
C2_2 Se1_2 C1_2 C1_2 178.1(3) . . . 2_566 ?
C2_2 Se1_2 C1_2 Se2_2 -3.70(14) . . . . ?
C1_2 Se1_2 C2_2 C3_2 2.5(2) . . . . ?
C2_3 Se1_3 C1_3 C1_3 177.9(3) . . . 2_665 ?
C2_3 Se1_3 C1_3 Se2_3 -1.78(15) . . . . ?
C1_3 Se1_3 C2_3 C3_3 1.2(3) . . . . ?
C2_4 Se1_4 C1_4 C1_4 -175.8(3) . . . 2_575 ?
C2_4 Se1_4 C1_4 Se2_4 6.31(16) . . . . ?
C1_4 Se1_4 C2_4 C3_4 -4.1(3) . . . . ?

_refine_diff_density_max         0.844
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.133


####################################################################### 
# 
# 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_TSTF-TCNQ_dmd15pt9
_database_code_depnum_ccdc_archive 'CCDC 1501345'
_audit_update_record             
;
2016-08-29 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H8 N4 S Se3'
_chemical_formula_weight         549.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14


_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4011(8)
_cell_length_b                   3.8012(3)
_cell_length_c                   18.4421(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.179(7)
_cell_angle_gamma                90
_cell_volume                     842.86(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    4554
_cell_measurement_theta_min      4.9340
_cell_measurement_theta_max      75.3980

_exptl_crystal_description       'needle like priamtic'
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.164
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    9.203
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  CrysAlisPro, Agilent Technologies,
  Version 1.171.37.35
  Empirical absorption correction using spherical 
  harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_crystal_treatment        
;
attached with Exxon Paratone N to a nylon loop and quenched 
in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. 
;


_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number            9226
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.676
_diffrn_reflns_theta_max         75.539
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1749
_reflns_number_gt                1598
_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       
;
  CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)
;
_computing_cell_refinement       
;
  CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)
;
_computing_data_reduction        
;
  CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)
;

_computing_structure_solution    'ShelxT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPIII  (Burnett, N.M., Johnson,C.K., 1996). 
  WinGX (Farrugia, 1999)
  shelXle (Hübschle,C.B., et al., 2011) 
;
_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)+(0.05P)²+11.0P] 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         1749
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1732
_refine_ls_goodness_of_fit_ref   1.403
_refine_ls_restrained_S_all      1.403
_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_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
Se1 Se -0.10123(7) 0.3098(3) 0.08146(5) 0.0208(3) Uani 0.7 1 d . . P . .
S1 S -0.10123(7) 0.3098(3) 0.08146(5) 0.0208(3) Uani 0.3 1 d . . P . .
Se2 Se 0.15531(7) 0.3127(3) 0.08851(5) 0.0222(3) Uani 0.8 1 d . . P . .
S2 S 0.15531(7) 0.3127(3) 0.08851(5) 0.0222(3) Uani 0.2 1 d . . P . .
C1 C 0.0115(5) 0.424(2) 0.0346(4) 0.0187(14) Uani 1 1 d . . . . .
C2 C -0.0019(7) 0.148(2) 0.1654(4) 0.0232(16) Uani 1 1 d . . . . .
H2 H -0.0283 0.0612 0.2063 0.028 Uiso 1 1 calc R U . . .
C3 C 0.1071(6) 0.150(2) 0.1697(4) 0.0235(16) Uani 1 1 d . . . . .
H3 H 0.1588 0.0697 0.2135 0.028 Uiso 1 1 calc R U . . .
N1 N 0.3854(5) 1.094(2) 0.1899(4) 0.0272(15) Uani 1 1 d . . . . .
N2 N 0.7456(5) 1.122(2) 0.1880(4) 0.0287(16) Uani 1 1 d . . . . .
C4 C 0.5236(6) 0.706(2) 0.0668(4) 0.0196(15) Uani 1 1 d . . . . .
C5 C 0.6088(6) 0.604(2) 0.0313(4) 0.0198(15) Uani 1 1 d . . . . .
H5 H 0.6830 0.6791 0.0523 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4124(6) 0.596(2) 0.0316(4) 0.0189(15) Uani 1 1 d . . . . .
H6 H 0.3528 0.6642 0.0525 0.023 Uiso 1 1 calc R U . . .
C7 C 0.5454(6) 0.913(2) 0.1313(4) 0.0189(15) Uani 1 1 d . . . . .
C8 C 0.4587(6) 1.015(2) 0.1659(4) 0.0197(15) Uani 1 1 d . . . . .
C9 C 0.6563(6) 1.029(2) 0.1657(4) 0.0206(15) 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
Se1 C2 1.834(8) . ?
Se1 C1 1.866(7) . ?
Se2 C3 1.850(7) . ?
Se2 C1 1.866(7) . ?
C1 C1 1.365(15) 3_565 ?
C2 C3 1.334(11) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
N1 C8 1.146(10) . ?
N2 C9 1.139(10) . ?
C4 C7 1.395(11) . ?
C4 C5 1.427(10) . ?
C4 C6 1.435(10) . ?
C5 C6 1.357(11) 3_665 ?
C5 H5 0.9500 . ?
C6 C5 1.357(11) 3_665 ?
C6 H6 0.9500 . ?
C7 C8 1.432(10) . ?
C7 C9 1.435(10) . ?

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 Se1 C1 92.6(3) . . ?
C3 Se2 C1 92.9(3) . . ?
C1 C1 Se1 121.6(7) 3_565 . ?
C1 C1 Se2 123.2(7) 3_565 . ?
Se1 C1 Se2 115.3(4) . . ?
C3 C2 Se1 120.6(6) . . ?
C3 C2 H2 119.7 . . ?
Se1 C2 H2 119.7 . . ?
C2 C3 Se2 118.5(6) . . ?
C2 C3 H3 120.7 . . ?
Se2 C3 H3 120.7 . . ?
C7 C4 C5 122.2(7) . . ?
C7 C4 C6 121.0(7) . . ?
C5 C4 C6 116.7(7) . . ?
C6 C5 C4 122.3(7) 3_665 . ?
C6 C5 H5 118.9 3_665 . ?
C4 C5 H5 118.9 . . ?
C5 C6 C4 121.0(7) 3_665 . ?
C5 C6 H6 119.5 3_665 . ?
C4 C6 H6 119.5 . . ?
C4 C7 C8 121.4(6) . . ?
C4 C7 C9 121.0(7) . . ?
C8 C7 C9 117.6(7) . . ?
N1 C8 C7 176.4(8) . . ?
N2 C9 C7 175.1(8) . . ?

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
C2 Se1 C1 C1 -178.2(10) . . . 3_565 ?
C2 Se1 C1 Se2 2.2(5) . . . . ?
C3 Se2 C1 C1 177.8(10) . . . 3_565 ?
C3 Se2 C1 Se1 -2.6(5) . . . . ?
C1 Se1 C2 C3 -0.7(8) . . . . ?
Se1 C2 C3 Se2 -1.1(10) . . . . ?
C1 Se2 C3 C2 2.2(8) . . . . ?
C7 C4 C5 C6 -179.8(8) . . . 3_665 ?
C6 C4 C5 C6 -1.9(13) . . . 3_665 ?
C7 C4 C6 C5 179.8(8) . . . 3_665 ?
C5 C4 C6 C5 1.9(13) . . . 3_665 ?
C5 C4 C7 C8 179.6(7) . . . . ?
C6 C4 C7 C8 1.8(12) . . . . ?
C5 C4 C7 C9 -1.0(12) . . . . ?
C6 C4 C7 C9 -178.8(7) . . . . ?

_refine_diff_density_max         1.018
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.197



####################################################################### 
# 
# 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_TCMTSTF_dmd15pt2_s1448
_database_code_depnum_ccdc_archive 'CCDC 1501344'
_audit_update_record             
;
2016-08-29 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 O8 S Se3'
_chemical_formula_weight         577.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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'


_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2


_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                   7.7902(2)
_cell_length_b                   8.6288(3)
_cell_length_c                   14.5566(4)
_cell_angle_alpha                100.073(3)
_cell_angle_beta                 105.219(3)
_cell_angle_gamma                96.116(3)
_cell_volume                     917.58(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    8109
_cell_measurement_theta_min      5.2400
_cell_measurement_theta_max      75.2220


_exptl_crystal_description       plate
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    8.755
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  CrysAlisPro, Agilent Technologies,
  Version 1.171.37.35
  Empirical absorption correction using spherical 
  harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_crystal_treatment        
;
attached with Exxon Paratone N to a nylon loop and quenched 
in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. 
;



_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number            14923
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_max         75.850
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3795
_reflns_number_gt                3524
_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       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_cell_refinement       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_data_reduction        
;
  CrysAlisPro, Agilent Technologies,
;

_computing_structure_solution    'ShelxT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPIII  (Burnett, N.M., Johnson,C.K., 1996). 
  WinGX (Farrugia, 1999)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_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)+(0.03P)²+3.0P] 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         3795
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.321
_refine_ls_restrained_S_all      1.321
_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
Se1 Se 0.22280(6) 0.38552(5) 0.52090(3) 0.02153(13) Uani 0.82 1 d . . P . .
S1 S 0.22280(6) 0.38552(5) 0.52090(3) 0.02153(13) Uani 0.18 1 d . . P . .
Se2 Se 0.26960(7) 0.67086(6) 0.41174(3) 0.02494(13) Uani 0.81 1 d . . P . .
S2 S 0.26960(7) 0.67086(6) 0.41174(3) 0.02494(13) Uani 0.19 1 d . . P . .
Se3 Se 0.54800(7) 0.89541(6) 0.61761(4) 0.02597(14) Uani 0.74 1 d . . P . .
S3 S 0.54800(7) 0.89541(6) 0.61761(4) 0.02597(14) Uani 0.26 1 d . . P . .
Se4 Se 0.49253(8) 0.61641(7) 0.72813(4) 0.02461(14) Uani 0.63 1 d . . P . .
S4 S 0.49253(8) 0.61641(7) 0.72813(4) 0.02461(14) Uani 0.37 1 d . . P . .
O1 O -0.1371(4) 0.1833(4) 0.2629(2) 0.0281(7) Uani 1 1 d . . . . .
O2 O -0.0082(4) 0.1071(3) 0.4014(2) 0.0251(6) Uani 1 1 d . . . . .
O3 O 0.0426(4) 0.4063(4) 0.1705(2) 0.0296(7) Uani 1 1 d . . . . .
O4 O -0.1069(4) 0.5805(3) 0.23848(19) 0.0228(6) Uani 1 1 d . . . . .
O5 O 0.8224(4) 1.1742(4) 0.7851(2) 0.0339(7) Uani 1 1 d . . . . .
O6 O 0.5933(4) 1.1812(3) 0.8510(2) 0.0248(6) Uani 1 1 d . . . . .
O7 O 0.6027(5) 0.7239(4) 0.9429(2) 0.0308(7) Uani 1 1 d . . . . .
O8 O 0.7539(4) 0.9665(4) 0.9541(2) 0.0293(7) Uani 1 1 d . . . . .
C1 C 0.3256(5) 0.5963(5) 0.5287(3) 0.0182(7) Uani 1 1 d . . . . .
C2 C 0.0900(5) 0.3632(5) 0.3898(3) 0.0184(7) Uani 1 1 d . . . . .
C3 C 0.1100(5) 0.4833(4) 0.3442(3) 0.0177(7) Uani 1 1 d . . . . .
C4 C -0.0325(5) 0.2103(5) 0.3424(3) 0.0188(7) Uani 1 1 d . . . . .
C5 C -0.1054(7) -0.0543(5) 0.3590(3) 0.0317(10) Uani 1 1 d . . . . .
H5A H -0.2351 -0.0515 0.3385 0.048 Uiso 1 1 calc R U . . .
H5B H -0.0794 -0.1206 0.4076 0.048 Uiso 1 1 calc R U . . .
H5C H -0.0669 -0.0991 0.3024 0.048 Uiso 1 1 calc R U . . .
C6 C 0.0118(5) 0.4813(5) 0.2395(3) 0.0201(8) Uani 1 1 d . . . . .
C7 C -0.2100(6) 0.5942(6) 0.1429(3) 0.0304(9) Uani 1 1 d . . . . .
H7A H -0.1287 0.6085 0.1027 0.046 Uiso 1 1 calc R U . . .
H7B H -0.2729 0.6863 0.1488 0.046 Uiso 1 1 calc R U . . .
H7C H -0.2983 0.4970 0.1122 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4352(5) 0.6881(4) 0.6117(3) 0.0179(7) Uani 1 1 d . . . . .
C9 C 0.6088(5) 0.9406(5) 0.7534(3) 0.0179(7) Uani 1 1 d . . . . .
C10 C 0.5895(5) 0.8215(5) 0.7995(3) 0.0192(7) Uani 1 1 d . . . . .
C11 C 0.6892(5) 1.1110(5) 0.7986(3) 0.0196(7) Uani 1 1 d . . . . .
C12 C 0.6775(7) 1.3396(5) 0.9083(3) 0.0322(10) Uani 1 1 d . . . . .
H12A H 0.7943 1.3333 0.9526 0.048 Uiso 1 1 calc R U . . .
H12B H 0.5994 1.3817 0.9463 0.048 Uiso 1 1 calc R U . . .
H12C H 0.6954 1.4103 0.8647 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6471(5) 0.8296(5) 0.9064(3) 0.0213(8) Uani 1 1 d . . . . .
C14 C 0.8032(7) 0.9950(6) 1.0599(3) 0.0335(10) Uani 1 1 d . . . . .
H14A H 0.6946 0.9750 1.0808 0.050 Uiso 1 1 calc R U . . .
H14B H 0.8616 1.1059 1.0873 0.050 Uiso 1 1 calc R U . . .
H14C H 0.8866 0.9232 1.0828 0.050 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
Se1 C1 1.880(4) . ?
Se1 C2 1.882(4) . ?
Se2 C3 1.872(4) . ?
Se2 C1 1.885(4) . ?
Se3 C9 1.867(4) . ?
Se3 C8 1.884(4) . ?
Se4 C10 1.855(4) . ?
Se4 C8 1.867(4) . ?
O1 C4 1.195(5) . ?
O2 C4 1.335(5) . ?
O2 C5 1.456(5) . ?
O3 C6 1.190(5) . ?
O4 C6 1.325(5) . ?
O4 C7 1.445(5) . ?
O5 C11 1.199(5) . ?
O6 C11 1.319(5) . ?
O6 C12 1.455(5) . ?
O7 C13 1.197(5) . ?
O8 C13 1.330(5) . ?
O8 C14 1.454(5) . ?
C1 C8 1.340(5) . ?
C2 C3 1.341(6) . ?
C2 C4 1.482(5) . ?
C3 C6 1.512(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.338(6) . ?
C9 C11 1.496(5) . ?
C10 C13 1.488(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C1 Se1 C2 92.18(17) . . ?
C3 Se2 C1 92.36(17) . . ?
C9 Se3 C8 91.07(16) . . ?
C10 Se4 C8 91.65(17) . . ?
C4 O2 C5 115.5(3) . . ?
C6 O4 C7 115.3(3) . . ?
C11 O6 C12 114.7(3) . . ?
C13 O8 C14 116.2(3) . . ?
C8 C1 Se1 122.4(3) . . ?
C8 C1 Se2 121.6(3) . . ?
Se1 C1 Se2 116.05(19) . . ?
C3 C2 C4 123.5(3) . . ?
C3 C2 Se1 119.6(3) . . ?
C4 C2 Se1 116.9(3) . . ?
C2 C3 C6 125.0(3) . . ?
C2 C3 Se2 119.6(3) . . ?
C6 C3 Se2 115.4(3) . . ?
O1 C4 O2 125.1(4) . . ?
O1 C4 C2 124.9(4) . . ?
O2 C4 C2 110.1(3) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 126.6(4) . . ?
O3 C6 C3 124.8(4) . . ?
O4 C6 C3 108.6(3) . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C8 Se4 122.2(3) . . ?
C1 C8 Se3 122.2(3) . . ?
Se4 C8 Se3 115.55(19) . . ?
C10 C9 C11 127.2(3) . . ?
C10 C9 Se3 119.2(3) . . ?
C11 C9 Se3 113.4(3) . . ?
C9 C10 C13 127.4(4) . . ?
C9 C10 Se4 119.9(3) . . ?
C13 C10 Se4 112.7(3) . . ?
O5 C11 O6 125.4(4) . . ?
O5 C11 C9 122.5(4) . . ?
O6 C11 C9 112.0(3) . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O7 C13 O8 125.4(4) . . ?
O7 C13 C10 123.1(4) . . ?
O8 C13 C10 111.4(3) . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C2 Se1 C1 C8 176.5(3) . . . . ?
C2 Se1 C1 Se2 -4.7(2) . . . . ?
C3 Se2 C1 C8 -176.4(3) . . . . ?
C3 Se2 C1 Se1 4.8(2) . . . . ?
C1 Se1 C2 C3 2.9(3) . . . . ?
C1 Se1 C2 C4 -177.2(3) . . . . ?
C4 C2 C3 C6 0.2(6) . . . . ?
Se1 C2 C3 C6 -179.9(3) . . . . ?
C4 C2 C3 Se2 -179.8(3) . . . . ?
Se1 C2 C3 Se2 0.1(4) . . . . ?
C1 Se2 C3 C2 -2.9(3) . . . . ?
C1 Se2 C3 C6 177.1(3) . . . . ?
C5 O2 C4 O1 6.6(6) . . . . ?
C5 O2 C4 C2 -173.1(3) . . . . ?
C3 C2 C4 O1 -7.1(6) . . . . ?
Se1 C2 C4 O1 173.0(3) . . . . ?
C3 C2 C4 O2 172.5(4) . . . . ?
Se1 C2 C4 O2 -7.3(4) . . . . ?
C7 O4 C6 O3 1.3(6) . . . . ?
C7 O4 C6 C3 178.9(3) . . . . ?
C2 C3 C6 O3 -72.9(6) . . . . ?
Se2 C3 C6 O3 107.1(4) . . . . ?
C2 C3 C6 O4 109.4(4) . . . . ?
Se2 C3 C6 O4 -70.6(4) . . . . ?
Se1 C1 C8 Se4 -1.2(5) . . . . ?
Se2 C1 C8 Se4 -179.90(19) . . . . ?
Se1 C1 C8 Se3 176.57(19) . . . . ?
Se2 C1 C8 Se3 -2.1(5) . . . . ?
C10 Se4 C8 C1 -167.0(4) . . . . ?
C10 Se4 C8 Se3 15.1(2) . . . . ?
C9 Se3 C8 C1 165.9(4) . . . . ?
C9 Se3 C8 Se4 -16.2(2) . . . . ?
C8 Se3 C9 C10 11.6(3) . . . . ?
C8 Se3 C9 C11 -172.9(3) . . . . ?
C11 C9 C10 C13 -1.5(7) . . . . ?
Se3 C9 C10 C13 173.3(3) . . . . ?
C11 C9 C10 Se4 -177.9(3) . . . . ?
Se3 C9 C10 Se4 -3.1(5) . . . . ?
C8 Se4 C10 C9 -7.4(3) . . . . ?
C8 Se4 C10 C13 175.7(3) . . . . ?
C12 O6 C11 O5 -10.5(6) . . . . ?
C12 O6 C11 C9 171.5(3) . . . . ?
C10 C9 C11 O5 117.3(5) . . . . ?
Se3 C9 C11 O5 -57.8(5) . . . . ?
C10 C9 C11 O6 -64.6(5) . . . . ?
Se3 C9 C11 O6 120.3(3) . . . . ?
C14 O8 C13 O7 -7.1(7) . . . . ?
C14 O8 C13 C10 173.8(4) . . . . ?
C9 C10 C13 O7 169.1(4) . . . . ?
Se4 C10 C13 O7 -14.3(5) . . . . ?
C9 C10 C13 O8 -11.7(6) . . . . ?
Se4 C10 C13 O8 164.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5A Se3 0.98 3.06 3.917(5) 146.5 2_566
C5 H5B Se1 0.98 2.91 3.754(5) 145.2 2_556
C5 H5C O5 0.98 2.63 3.534(6) 153.3 2_666
C12 H12C Se4 0.98 3.13 3.950(5) 142.2 1_565
C14 H14B O1 0.98 2.52 3.005(5) 110.1 1_666

_refine_diff_density_max         0.617
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.099


