# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1827732'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H N O S'
_chemical_formula_weight         75.09

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.563(9)
_cell_length_b                   10.201(10)
_cell_length_c                   16.616(16)
_cell_angle_alpha                89.822(15)
_cell_angle_beta                 89.865(16)
_cell_angle_gamma                76.378(15)
_cell_volume                     1575(3)
_cell_formula_units_Z            20
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9305
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0991
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         29.82
_reflns_number_total             7253
_reflns_number_gt                3184
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.023(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7253
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2602
_refine_ls_R_factor_gt           0.1623
_refine_ls_wR_factor_ref         0.4820
_refine_ls_wR_factor_gt          0.4267
_refine_ls_goodness_of_fit_ref   1.474
_refine_ls_restrained_S_all      1.474
_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
S1 S 0.3298(4) 1.2635(2) 0.24886(19) 0.1171(11) Uani 1 1 d . . .
S2 S 0.8301(4) 1.2625(2) 0.25114(19) 0.1179(11) Uani 1 1 d . . .
O2 O 0.4295(5) 0.9779(4) 0.2973(3) 0.0633(13) Uani 1 1 d . . .
O4 O 0.9307(5) 0.9780(4) 0.2028(3) 0.0627(13) Uani 1 1 d . . .
N5 N 0.7562(6) 0.8078(5) 0.1996(3) 0.0553(13) Uani 1 1 d . . .
C28 C 0.8164(6) 1.0059(5) 0.2396(4) 0.0498(14) Uani 1 1 d . . .
N1 N 0.2559(6) 0.8079(5) 0.3003(3) 0.0562(14) Uani 1 1 d . . .
O3 O 0.8908(5) 0.6350(4) 0.0939(3) 0.0696(14) Uani 1 1 d . . .
C14 C 0.1759(5) 1.1514(5) 0.1348(3) 0.0454(14) Uani 1 1 d . . .
N2 N 0.2245(6) 0.9257(4) 0.2566(3) 0.0531(13) Uani 1 1 d . . .
C17 C 0.6583(7) 0.7392(5) 0.2014(4) 0.0541(15) Uani 1 1 d . . .
C1 C 0.1583(7) 0.7395(5) 0.2998(4) 0.0542(16) Uani 1 1 d . . .
C2 C 0.1683(7) 0.6235(5) 0.3467(4) 0.0513(15) Uani 1 1 d . . .
N4 N 0.7251(6) 0.9263(4) 0.2438(3) 0.0531(13) Uani 1 1 d . . .
C5 C 0.1736(7) 0.3987(6) 0.4449(4) 0.0602(17) Uani 1 1 d . . .
C30 C 0.6757(6) 1.1514(5) 0.3655(3) 0.0448(14) Uani 1 1 d . . .
C12 C 0.3151(7) 1.0053(5) 0.2604(4) 0.0510(15) Uani 1 1 d . . .
O1 O 0.3919(5) 0.6358(4) 0.4072(3) 0.0693(14) Uani 1 1 d . . .
C21 C 0.6735(8) 0.3975(6) 0.0546(4) 0.0606(17) Uani 1 1 d . . .
C23 C 0.7841(7) 0.5736(6) 0.0993(4) 0.0565(16) Uani 1 1 d . . .
C18 C 0.6693(7) 0.6230(5) 0.1536(4) 0.0518(15) Uani 1 1 d . . .
C22 C 0.7842(7) 0.4670(6) 0.0523(4) 0.0621(18) Uani 1 1 d . . .
C19 C 0.5605(7) 0.5518(6) 0.1561(4) 0.0602(17) Uani 1 1 d . . .
C13 C 0.2707(7) 1.1349(6) 0.2185(4) 0.0589(18) Uani 1 1 d . . .
C7 C 0.2857(7) 0.5759(5) 0.4006(4) 0.0541(16) Uani 1 1 d . . .
C20 C 0.5619(8) 0.4431(6) 0.1101(5) 0.0668(19) Uani 1 1 d . . .
C4 C 0.0622(8) 0.4428(6) 0.3899(5) 0.0654(19) Uani 1 1 d . . .
C6 C 0.2851(7) 0.4643(6) 0.4467(4) 0.0624(18) Uani 1 1 d . . .
N3 N 0.1744(7) 0.2911(6) 0.4953(5) 0.082(2) Uani 1 1 d . . .
N6 N 0.6729(8) 0.2925(6) 0.0054(5) 0.084(2) Uani 1 1 d . . .
C3 C 0.0611(7) 0.5534(6) 0.3444(5) 0.0634(18) Uani 1 1 d . . .
C29 C 0.7745(7) 1.1366(6) 0.2806(4) 0.0612(17) Uani 1 1 d . . .
C8 C 0.0597(9) 0.2206(7) 0.4935(5) 0.080(2) Uani 1 1 d . . .
C24 C 0.5584(10) 0.2210(7) 0.0056(5) 0.079(2) Uani 1 1 d . . .
C32 C 0.7396(11) 1.3635(7) 0.3165(6) 0.093(3) Uani 1 1 d . . .
C16 C 0.2441(11) 1.3660(8) 0.1844(7) 0.092(3) Uani 1 1 d . . .
C10 C 0.2899(14) 0.2529(9) 0.5615(8) 0.126(4) Uani 1 1 d . . .
C26 C 0.7894(14) 0.2528(10) -0.0613(7) 0.115(4) Uani 1 1 d . . .
C31 C 0.6627(10) 1.3093(9) 0.3687(8) 0.111(3) Uani 1 1 d . . .
C15 C 0.1695(12) 1.3118(10) 0.1309(8) 0.114(4) Uani 1 1 d . . .
C25 C 0.5767(11) 0.1142(8) 0.0739(6) 0.096(3) Uani 1 1 d . . .
C9 C 0.0817(12) 0.1175(8) 0.4252(6) 0.095(3) Uani 1 1 d . . .
C27 C 0.9156(18) 0.1534(12) -0.0207(10) 0.153(5) Uani 1 1 d . . .
C11 C 0.4144(16) 0.1559(11) 0.5213(10) 0.145(5) 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
S1 C16 1.583(10) . ?
S1 C13 1.628(8) . ?
S2 C29 1.578(7) . ?
S2 C32 1.604(10) . ?
O2 C12 1.229(8) . ?
O4 C28 1.225(7) . ?
N5 C17 1.294(8) . ?
N5 N4 1.388(7) . ?
C28 N4 1.326(7) . ?
C28 C29 1.468(8) . ?
N1 C1 1.290(8) . ?
N1 N2 1.374(6) . ?
O3 C23 1.320(7) . ?
C14 C15 1.624(11) . ?
C14 C13 1.648(10) . ?
N2 C12 1.321(8) . ?
C17 C18 1.412(8) . ?
C1 C2 1.400(7) . ?
C2 C3 1.382(9) . ?
C2 C7 1.429(10) . ?
C5 N3 1.377(7) . ?
C5 C6 1.387(9) . ?
C5 C4 1.395(11) . ?
C30 C31 1.586(10) . ?
C30 C29 1.684(8) . ?
C12 C13 1.464(8) . ?
O1 C7 1.309(7) . ?
C21 N6 1.350(9) . ?
C21 C20 1.404(9) . ?
C21 C22 1.407(9) . ?
C23 C22 1.340(9) . ?
C23 C18 1.418(8) . ?
C18 C19 1.403(8) . ?
C19 C20 1.346(10) . ?
C7 C6 1.371(8) . ?
C4 C3 1.354(8) . ?
N3 C8 1.447(10) . ?
N3 C10 1.543(16) . ?
N6 C24 1.452(10) . ?
N6 C26 1.555(13) . ?
C8 C9 1.530(12) . ?
C24 C25 1.553(10) . ?
C32 C31 1.335(14) . ?
C16 C15 1.339(17) . ?
C10 C11 1.513(17) . ?
C26 C27 1.54(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
C16 S1 C13 95.5(5) . . ?
C29 S2 C32 94.6(4) . . ?
C17 N5 N4 115.2(5) . . ?
O4 C28 N4 124.2(5) . . ?
O4 C28 C29 118.7(6) . . ?
N4 C28 C29 117.1(5) . . ?
C1 N1 N2 115.5(5) . . ?
C15 C14 C13 91.3(7) . . ?
C12 N2 N1 118.1(5) . . ?
N5 C17 C18 121.5(6) . . ?
N1 C1 C2 122.5(6) . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 C7 117.6(5) . . ?
C1 C2 C7 121.8(6) . . ?
C28 N4 N5 118.0(5) . . ?
N3 C5 C6 120.6(6) . . ?
N3 C5 C4 121.0(6) . . ?
C6 C5 C4 118.4(5) . . ?
C31 C30 C29 91.7(5) . . ?
O2 C12 N2 124.3(5) . . ?
O2 C12 C13 119.7(6) . . ?
N2 C12 C13 116.0(6) . . ?
N6 C21 C20 121.2(6) . . ?
N6 C21 C22 122.0(6) . . ?
C20 C21 C22 116.9(6) . . ?
O3 C23 C22 119.6(6) . . ?
O3 C23 C18 119.5(6) . . ?
C22 C23 C18 120.8(6) . . ?
C19 C18 C17 120.2(5) . . ?
C19 C18 C23 116.0(6) . . ?
C17 C18 C23 123.8(6) . . ?
C23 C22 C21 122.6(6) . . ?
C20 C19 C18 123.2(6) . . ?
C12 C13 S1 119.9(6) . . ?
C12 C13 C14 121.8(6) . . ?
S1 C13 C14 118.0(4) . . ?
O1 C7 C6 119.7(6) . . ?
O1 C7 C2 122.0(5) . . ?
C6 C7 C2 118.3(6) . . ?
C19 C20 C21 120.4(6) . . ?
C3 C4 C5 119.2(7) . . ?
C7 C6 C5 122.7(6) . . ?
C5 N3 C8 121.3(6) . . ?
C5 N3 C10 120.2(7) . . ?
C8 N3 C10 118.2(6) . . ?
C21 N6 C24 122.9(6) . . ?
C21 N6 C26 120.2(7) . . ?
C24 N6 C26 116.6(7) . . ?
C4 C3 C2 123.6(7) . . ?
C28 C29 S2 121.6(5) . . ?
C28 C29 C30 119.9(5) . . ?
S2 C29 C30 118.2(4) . . ?
N3 C8 C9 111.2(7) . . ?
N6 C24 C25 112.2(7) . . ?
C31 C32 S2 116.0(6) . . ?
C15 C16 S1 114.9(6) . . ?
C11 C10 N3 104.9(11) . . ?
C27 C26 N6 105.1(10) . . ?
C32 C31 C30 118.6(7) . . ?
C16 C15 C14 119.6(8) . . ?

_diffrn_measured_fraction_theta_max 0.800
_diffrn_reflns_theta_full        29.82
_diffrn_measured_fraction_theta_full 0.800
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.148
