# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2223882'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universite Rennes
France
;
_audit_update_record             
;
2022-12-02 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;

_audit_creation_date             2021-12-01T11:16:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H16 N O2 S8'
_chemical_formula_moiety         'C16 H16 N O2 S8'
_chemical_formula_weight         510.78

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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
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                   6.9491(6)
_cell_length_b                   12.3251(10)
_cell_length_c                   12.0663(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.318(3)
_cell_angle_gamma                90
_cell_volume                     1005.67(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             526

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.991

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6875  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.9221                          #
#------------------------------------------------------------------------------#
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_orient_matrix_ub_11      0.043886
_diffrn_orient_matrix_ub_12      0.066822
_diffrn_orient_matrix_ub_13      -0.034236
_diffrn_orient_matrix_ub_21      0.080547
_diffrn_orient_matrix_ub_22      0.021887
_diffrn_orient_matrix_ub_23      0.076495
_diffrn_orient_matrix_ub_31      0.115994
_diffrn_orient_matrix_ub_32      -0.040481
_diffrn_orient_matrix_ub_33      -0.015155
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thicn slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_number            15795
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.396
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             2295
_reflns_number_gt                1939
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+0.5704P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2295
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.158

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.2470(2) 0.50178(14) 0.49391(14) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.1734(2) 0.68111(14) 0.38020(15) 0.0157(4) Uani 1 1 d . . . . .
C3 C 0.1444(2) 0.60277(15) 0.30092(15) 0.0161(4) Uani 1 1 d . . . . .
C4 C 0.1558(3) 0.80126(15) 0.36237(17) 0.0219(4) Uani 1 1 d . . . . .
H4A H 0.1237 0.8171 0.2806 0.033 Uiso 1 1 calc R U . . .
H4B H 0.2815 0.836 0.3984 0.033 Uiso 1 1 calc R U . . .
H4C H 0.0508 0.8294 0.3964 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0848(3) 0.61444(16) 0.17399(15) 0.0225(4) Uani 1 1 d . . . . .
H5A H 0.073 0.6916 0.1539 0.034 Uiso 1 1 calc R U . . .
H5B H -0.0427 0.5785 0.1452 0.034 Uiso 1 1 calc R U . . .
H5C H 0.1852 0.5809 0.1398 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2960(2) 0.42458(14) 0.57684(14) 0.0135(3) Uani 1 1 d . . . . .
C7 C 0.3718(3) 0.24652(15) 0.68543(16) 0.0194(4) Uani 1 1 d . . . . .
H7 H 0.3907 0.1721 0.7053 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3991(3) 0.32356(15) 0.76501(15) 0.0202(4) Uani 1 1 d . . . . .
H8 H 0.4375 0.3057 0.8436 0.024 Uiso 1 1 calc R U . . .
N1 N 0.4962(7) 0.0147(3) 0.4763(3) 0.0174(8) Uani 0.5 1 d . . P . .
O1 O 0.3908(3) 0.04847(16) 0.5223(2) 0.0631(6) Uani 1 1 d . . . . .
S1 S 0.24466(6) 0.63936(3) 0.52267(3) 0.01517(12) Uani 1 1 d . . . . .
S2 S 0.18164(6) 0.46914(3) 0.35056(3) 0.01544(12) Uani 1 1 d . . . . .
S3 S 0.30066(6) 0.28700(3) 0.54489(4) 0.01585(12) Uani 1 1 d . . . . .
S4 S 0.36259(6) 0.45704(4) 0.72093(3) 0.01581(12) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.366(2) . ?
C1 S2 1.7315(17) . ?
C1 S1 1.7316(18) . ?
C2 C3 1.341(3) . ?
C2 C4 1.497(2) . ?
C2 S1 1.7529(17) . ?
C3 C5 1.499(2) . ?
C3 S2 1.7512(18) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 S4 1.7396(17) . ?
C6 S3 1.7408(18) . ?
C7 C8 1.333(3) . ?
C7 S3 1.7271(18) . ?
C7 H7 0.95 . ?
C8 S4 1.7297(19) . ?
C8 H8 0.95 . ?
N1 N1 0.669(5) 3_656 ?
N1 O1 1.098(5) . ?
N1 O1 1.103(5) 3_656 ?
O1 N1 1.103(5) 3_656 ?

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 C1 S2 122.26(14) . . ?
C6 C1 S1 123.20(13) . . ?
S2 C1 S1 114.54(10) . . ?
C3 C2 C4 127.99(17) . . ?
C3 C2 S1 116.76(13) . . ?
C4 C2 S1 115.25(14) . . ?
C2 C3 C5 128.35(17) . . ?
C2 C3 S2 116.55(13) . . ?
C5 C3 S2 115.09(14) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 S4 122.41(14) . . ?
C1 C6 S3 122.04(13) . . ?
S4 C6 S3 115.54(10) . . ?
C8 C7 S3 117.57(14) . . ?
C8 C7 H7 121.2 . . ?
S3 C7 H7 121.2 . . ?
C7 C8 S4 118.01(14) . . ?
C7 C8 H8 121 . . ?
S4 C8 H8 121 . . ?
N1 N1 O1 72.7(8) 3_656 . ?
N1 N1 O1 71.9(8) 3_656 3_656 ?
O1 N1 O1 144.6(3) . 3_656 ?
N1 O1 N1 35.4(3) . 3_656 ?
C1 S1 C2 96.00(8) . . ?
C1 S2 C3 96.15(8) . . ?
C7 S3 C6 94.57(9) . . ?
C8 S4 C6 94.30(9) . . ?

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
C4 C2 C3 C5 -0.7(3) . . . . ?
S1 C2 C3 C5 -179.61(15) . . . . ?
C4 C2 C3 S2 178.89(14) . . . . ?
S1 C2 C3 S2 0.03(19) . . . . ?
S2 C1 C6 S4 179.78(9) . . . . ?
S1 C1 C6 S4 -0.3(2) . . . . ?
S2 C1 C6 S3 1.1(2) . . . . ?
S1 C1 C6 S3 -178.97(9) . . . . ?
S3 C7 C8 S4 -0.4(2) . . . . ?
O1 N1 O1 N1 -0.0040(10) 3_656 . . 3_656 ?
C6 C1 S1 C2 179.48(15) . . . . ?
S2 C1 S1 C2 -0.56(11) . . . . ?
C3 C2 S1 C1 0.33(15) . . . . ?
C4 C2 S1 C1 -178.68(13) . . . . ?
C6 C1 S2 C3 -179.46(14) . . . . ?
S1 C1 S2 C3 0.58(11) . . . . ?
C2 C3 S2 C1 -0.36(15) . . . . ?
C5 C3 S2 C1 179.32(13) . . . . ?
C8 C7 S3 C6 -0.40(16) . . . . ?
C1 C6 S3 C7 179.83(15) . . . . ?
S4 C6 S3 C7 1.04(11) . . . . ?
C7 C8 S4 C6 0.94(16) . . . . ?
C1 C6 S4 C8 -179.97(15) . . . . ?
S3 C6 S4 C8 -1.18(11) . . . . ?



# END of CIF
_chemical_name_systematic        (o-DMTTF)2NO2
_exptl_crystal_recrystallization_method Electrocrystallization
_exptl_crystal_preparation       'Magnetic properties'
