# 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_640m_a
_database_code_depnum_ccdc_archive 'CCDC 1570355'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-03-07 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            'C15 H22 N6 O S2'
_chemical_formula_weight         366.51

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.6287(9)
_cell_length_b                   4.8391(3)
_cell_length_c                   26.5329(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.637(4)
_cell_angle_gamma                90
_cell_volume                     1865.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    3025
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      24.95

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.755
_exptl_transmission_factor_max   0.865
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.321
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15121
_diffrn_reflns_av_unetI/netI     0.0990
_diffrn_reflns_av_R_equivalents  0.1549
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.567
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3281
_reflns_number_gt                1786
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1003P)²+4.9693P] 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         3281
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1811
_refine_ls_R_factor_gt           0.1022
_refine_ls_wR_factor_ref         0.2895
_refine_ls_wR_factor_gt          0.2472
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

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
S2 S 0.69462(14) -0.4474(4) 0.17684(8) 0.0587(6) Uani 1 1 d . . . . .
S1 S 0.64849(19) 1.5871(6) 0.51651(9) 0.0872(9) Uani 1 1 d . . . . .
O1 O 0.6087(3) 0.6830(10) 0.34624(18) 0.0559(14) Uani 1 1 d . . . . .
H1 H 0.6155 0.8025 0.3683 0.084 Uiso 1 1 calc R U . . .
N4 N 0.6190(4) -0.0744(12) 0.2302(2) 0.0493(15) Uani 1 1 d . . . . .
H4 H 0.6740 -0.0353 0.2432 0.059 Uiso 1 1 calc R U . . .
N3 N 0.5451(4) 0.0647(12) 0.2462(2) 0.0462(14) Uani 1 1 d . . . . .
N1 N 0.5542(5) 1.0501(12) 0.4128(2) 0.0535(16) Uani 1 1 d . . . . .
N2 N 0.5638(5) 1.2418(13) 0.4514(2) 0.0620(18) Uani 1 1 d . . . . .
H2 H 0.5165 1.2803 0.4666 0.074 Uiso 1 1 calc R U . . .
C1 C 0.5184(5) 0.6122(14) 0.3377(2) 0.0419(16) Uani 1 1 d . . . . .
N5 N 0.5188(5) -0.3112(14) 0.1757(2) 0.0668(19) Uani 1 1 d . . . . .
H7 H 0.4787 -0.2014 0.1860 0.080 Uiso 1 1 calc R U . . .
C11 C 0.6053(5) -0.2698(14) 0.1943(3) 0.0430(17) Uani 1 1 d . . . . .
C6 C 0.4520(5) 0.7400(14) 0.3641(2) 0.0451(17) Uani 1 1 d . . . . .
C2 C 0.4945(5) 0.4004(13) 0.3024(2) 0.0430(17) Uani 1 1 d . . . . .
C8 C 0.5657(5) 0.2564(14) 0.2789(2) 0.0444(17) Uani 1 1 d . . . . .
H8 H 0.6271 0.3040 0.2876 0.053 Uiso 1 1 calc R U . . .
C3 C 0.4034(5) 0.3258(14) 0.2942(3) 0.0491(18) Uani 1 1 d . . . . .
H3 H 0.3862 0.1875 0.2707 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4733(6) 0.9470(15) 0.4018(3) 0.0557(19) Uani 1 1 d . . . . .
H9 H 0.4261 1.0109 0.4195 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3620(5) 0.6500(15) 0.3543(3) 0.0536(19) Uani 1 1 d . . . . .
H5 H 0.3176 0.7299 0.3720 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3357(5) 0.4480(16) 0.3195(3) 0.0542(19) Uani 1 1 d . . . . .
N6 N 0.7123(6) 1.3216(18) 0.4402(3) 0.093(3) Uani 1 1 d . . . . .
H6 H 0.7102 1.1750 0.4218 0.111 Uiso 1 1 calc R U . . .
C10 C 0.6435(6) 1.3720(17) 0.4665(3) 0.061(2) Uani 1 1 d . . . . .
C7 C 0.2377(6) 0.344(2) 0.3111(4) 0.081(3) Uani 1 1 d . . . . .
H7A H 0.2347 0.1618 0.3252 0.121 Uiso 1 1 calc R U . . .
H7B H 0.2177 0.3370 0.2753 0.121 Uiso 1 1 calc R U . . .
H7C H 0.1985 0.4660 0.3273 0.121 Uiso 1 1 calc R U . . .
C12 C 0.4839(8) -0.526(2) 0.1391(4) 0.107(4) Uani 1 1 d . . . . .
H12A H 0.5360 -0.6290 0.1294 0.128 Uiso 1 1 calc R U . . .
H12B H 0.4464 -0.6531 0.1560 0.128 Uiso 1 1 calc R U . . .
C13 C 0.4323(11) -0.432(4) 0.0952(5) 0.186(8) Uani 1 1 d . . . . .
H13A H 0.3953 -0.2779 0.1033 0.279 Uiso 1 1 calc R U . . .
H13B H 0.3931 -0.5779 0.0809 0.279 Uiso 1 1 calc R U . . .
H13C H 0.4728 -0.3754 0.0712 0.279 Uiso 1 1 calc R U . . .
C16 C 0.8104(14) 1.544(3) 0.4408(5) 0.174(8) Uani 1 1 d . . . . .
H16A H 0.8391 1.5439 0.4097 0.209 Uiso 1 1 calc R U . . .
H16B H 0.8012 1.7295 0.4530 0.209 Uiso 1 1 calc R U . . .
C17 C 0.8457(14) 1.377(4) 0.4744(7) 0.189(8) Uani 1 1 d . . . . .
H17A H 0.8073 1.3657 0.5013 0.284 Uiso 1 1 calc R U . . .
H17B H 0.9057 1.4418 0.4877 0.284 Uiso 1 1 calc R U . . .
H17C H 0.8510 1.1976 0.4596 0.284 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
S2 C11 1.673(7) . ?
S1 C10 1.682(8) . ?
O1 C1 1.358(8) . ?
O1 H1 0.8200 . ?
N4 C11 1.339(8) . ?
N4 N3 1.383(8) . ?
N4 H4 0.8600 . ?
N3 C8 1.281(8) . ?
N1 C9 1.287(9) . ?
N1 N2 1.376(8) . ?
N2 C10 1.345(10) . ?
N2 H2 0.8600 . ?
C1 C2 1.404(9) . ?
C1 C6 1.405(9) . ?
N5 C11 1.320(9) . ?
N5 C12 1.473(11) . ?
N5 H7 0.8600 . ?
C6 C5 1.382(10) . ?
C6 C9 1.426(10) . ?
C2 C3 1.374(9) . ?
C2 C8 1.453(9) . ?
C8 H8 0.9300 . ?
C3 C4 1.392(10) . ?
C3 H3 0.9300 . ?
C9 H9 0.9300 . ?
C5 C4 1.368(10) . ?
C5 H5 0.9300 . ?
C4 C7 1.512(11) . ?
N6 C10 1.312(10) . ?
N6 C16 1.79(2) . ?
N6 H6 0.8600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C12 C13 1.387(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C16 C17 1.266(18) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 O1 H1 109.5 . . ?
C11 N4 N3 120.3(6) . . ?
C11 N4 H4 119.8 . . ?
N3 N4 H4 119.8 . . ?
C8 N3 N4 115.4(6) . . ?
C9 N1 N2 116.2(6) . . ?
C10 N2 N1 123.2(7) . . ?
C10 N2 H2 118.4 . . ?
N1 N2 H2 118.4 . . ?
O1 C1 C2 117.3(6) . . ?
O1 C1 C6 121.3(6) . . ?
C2 C1 C6 121.4(6) . . ?
C11 N5 C12 126.8(7) . . ?
C11 N5 H7 116.6 . . ?
C12 N5 H7 116.6 . . ?
N5 C11 N4 115.5(6) . . ?
N5 C11 S2 124.3(6) . . ?
N4 C11 S2 120.1(5) . . ?
C5 C6 C1 117.8(6) . . ?
C5 C6 C9 118.6(7) . . ?
C1 C6 C9 123.5(7) . . ?
C3 C2 C1 117.3(6) . . ?
C3 C2 C8 122.5(6) . . ?
C1 C2 C8 120.1(6) . . ?
N3 C8 C2 120.8(7) . . ?
N3 C8 H8 119.6 . . ?
C2 C8 H8 119.6 . . ?
C2 C3 C4 122.9(7) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
N1 C9 C6 123.5(7) . . ?
N1 C9 H9 118.2 . . ?
C6 C9 H9 118.2 . . ?
C4 C5 C6 122.6(7) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C4 C3 117.9(7) . . ?
C5 C4 C7 121.8(7) . . ?
C3 C4 C7 120.1(7) . . ?
C10 N6 C16 123.1(8) . . ?
C10 N6 H6 118.4 . . ?
C16 N6 H6 118.4 . . ?
N6 C10 N2 116.5(7) . . ?
N6 C10 S1 124.7(7) . . ?
N2 C10 S1 118.8(6) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C12 N5 115.9(11) . . ?
C13 C12 H12A 108.3 . . ?
N5 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
N5 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C16 N6 83.5(15) . . ?
C17 C16 H16A 114.7 . . ?
N6 C16 H16A 114.7 . . ?
C17 C16 H16B 114.7 . . ?
N6 C16 H16B 114.7 . . ?
H16A C16 H16B 111.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.079

