# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2006348'
loop_
_audit_author_name
_audit_author_address
'Subhas Samanta'
;Department of Chemistry, University of Calcutta
India
;
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N4 S2'
_chemical_formula_sum            'C14 H18 N4 S2'
_chemical_formula_weight         306.44

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.8868(8)
_cell_length_b                   14.8106(17)
_cell_length_c                   15.0914(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1539.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    24711
_cell_measurement_theta_min      3.030
_cell_measurement_theta_max      30.203

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.342
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker-AXS SMART APEXII diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24711
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_max         30.203
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4357
_reflns_number_gt                4065
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²] 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_abs_structure_details 
;
 Flack x determined using 1668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4357
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
S1 S 0.51762(7) 0.34554(3) 0.24961(3) 0.04553(15) Uani 1 1 d . . . . .
S2 S 0.81256(9) 0.45212(3) 0.56932(4) 0.05035(16) Uani 1 1 d . . . . .
N1 N 0.5465(2) 0.45438(10) 0.43210(10) 0.0394(3) Uani 1 1 d . . . . .
N2 N 0.4019(2) 0.45795(11) 0.38168(11) 0.0406(3) Uani 1 1 d . . . . .
N3 N 0.0077(2) 0.60782(12) 0.38435(14) 0.0475(4) Uani 1 1 d . . . . .
N4 N 0.0950(3) 0.64057(12) 0.45888(13) 0.0489(4) Uani 1 1 d . . . . .
C2 C 0.6865(3) 0.33089(11) 0.33614(12) 0.0387(3) Uani 1 1 d . . . . .
C1 C 0.6816(3) 0.38593(11) 0.41327(12) 0.0366(3) Uani 1 1 d . . . . .
C10 C 0.1056(3) 0.53905(13) 0.34752(14) 0.0416(4) Uani 1 1 d . . . . .
C3 C 0.8351(3) 0.26680(14) 0.32947(15) 0.0491(5) Uani 1 1 d . . . . .
H3 H 0.841429 0.229873 0.279711 0.059 Uiso 1 1 calc R U . . .
C9 C 0.2682(3) 0.52648(12) 0.40004(12) 0.0378(3) Uani 1 1 d . . . . .
C6 C 0.8271(3) 0.37707(13) 0.47885(13) 0.0414(4) Uani 1 1 d . . . . .
C11 C 0.2569(3) 0.59224(13) 0.46934(13) 0.0424(4) Uani 1 1 d . . . . .
C5 C 0.9713(4) 0.31231(16) 0.46988(17) 0.0545(5) Uani 1 1 d . . . . .
H5 H 1.066120 0.305788 0.513285 0.065 Uiso 1 1 calc R U . . .
C13 C 0.0440(3) 0.49142(18) 0.26584(16) 0.0560(5) Uani 1 1 d . . . . .
H13A H -0.078125 0.461968 0.276071 0.084 Uiso 1 1 calc R U . . .
H13B H 0.139978 0.447240 0.250074 0.084 Uiso 1 1 calc R U . . .
H13C H 0.030259 0.534211 0.218470 0.084 Uiso 1 1 calc R U . . .
C4 C 0.9724(4) 0.25741(16) 0.39543(17) 0.0598(6) Uani 1 1 d . . . . .
H4 H 1.067805 0.213312 0.389843 0.072 Uiso 1 1 calc R U . . .
C7 C 0.6270(4) 0.2822(2) 0.16086(15) 0.0623(6) Uani 1 1 d . . . . .
H7A H 0.757140 0.303314 0.151277 0.093 Uiso 1 1 calc R U . . .
H7B H 0.552418 0.290257 0.107703 0.093 Uiso 1 1 calc R U . . .
H7C H 0.629799 0.219357 0.176276 0.093 Uiso 1 1 calc R U . . .
C14 C -0.1790(3) 0.64452(18) 0.3562(2) 0.0671(7) Uani 1 1 d . . . . .
H14A H -0.168489 0.666686 0.296619 0.101 Uiso 1 1 calc R U . . .
H14B H -0.215639 0.693073 0.394890 0.101 Uiso 1 1 calc R U . . .
H14C H -0.275825 0.597933 0.358577 0.101 Uiso 1 1 calc R U . . .
C12 C 0.3888(5) 0.61086(18) 0.54346(16) 0.0615(6) Uani 1 1 d . . . . .
H12A H 0.502014 0.641647 0.521873 0.092 Uiso 1 1 calc R U . . .
H12B H 0.426815 0.555017 0.570709 0.092 Uiso 1 1 calc R U . . .
H12C H 0.323984 0.648104 0.586296 0.092 Uiso 1 1 calc R U . . .
C8 C 1.0147(5) 0.4191(2) 0.6361(2) 0.0739(8) Uani 1 1 d . . . . .
H8A H 0.996686 0.358129 0.656030 0.111 Uiso 1 1 calc R U . . .
H8B H 1.024119 0.458520 0.686481 0.111 Uiso 1 1 calc R U . . .
H8C H 1.131736 0.423019 0.601834 0.111 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
S1 C2 1.762(2) . ?
S1 C7 1.800(2) . ?
S2 C6 1.763(2) . ?
S2 C8 1.787(3) . ?
N1 N2 1.254(2) . ?
N1 C1 1.405(2) . ?
N2 C9 1.398(2) . ?
N3 C10 1.342(2) . ?
N3 N4 1.365(3) . ?
N3 C14 1.459(3) . ?
N4 C11 1.334(3) . ?
C2 C3 1.399(3) . ?
C2 C1 1.421(2) . ?
C1 C6 1.414(3) . ?
C10 C9 1.384(3) . ?
C10 C13 1.482(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C9 C11 1.431(3) . ?
C6 C5 1.387(3) . ?
C11 C12 1.467(3) . ?
C5 C4 1.387(3) . ?
C5 H5 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 H4 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C2 S1 C7 102.18(10) . . ?
C6 S2 C8 102.73(12) . . ?
N2 N1 C1 115.69(15) . . ?
N1 N2 C9 115.67(16) . . ?
C10 N3 N4 112.93(17) . . ?
C10 N3 C14 127.2(2) . . ?
N4 N3 C14 119.73(19) . . ?
C11 N4 N3 105.97(16) . . ?
C3 C2 C1 117.72(18) . . ?
C3 C2 S1 120.86(15) . . ?
C1 C2 S1 121.37(13) . . ?
N1 C1 C6 113.25(16) . . ?
N1 C1 C2 126.51(16) . . ?
C6 C1 C2 120.19(16) . . ?
N3 C10 C9 105.75(18) . . ?
N3 C10 C13 124.17(19) . . ?
C9 C10 C13 130.07(18) . . ?
C4 C3 C2 121.17(19) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C10 C9 N2 121.11(17) . . ?
C10 C9 C11 106.44(16) . . ?
N2 C9 C11 132.42(17) . . ?
C5 C6 C1 120.20(18) . . ?
C5 C6 S2 123.52(16) . . ?
C1 C6 S2 116.28(13) . . ?
N4 C11 C9 108.90(18) . . ?
N4 C11 C12 120.45(18) . . ?
C9 C11 C12 130.65(18) . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C4 C5 121.42(19) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S2 C8 H8A 109.5 . . ?
S2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol-Diethyl ether'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2006349'
loop_
_audit_author_name
_audit_author_address
'Subhas Samanta'
;Department of Chemistry, University of Calcutta
India
;
_audit_update_record             
;
2020-07-10 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_audit_creation_date             2020-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 N4 S'
_chemical_formula_sum            'C13 H16 N4 S'
_chemical_formula_weight         260.36
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9549(12)
_cell_length_b                   8.8714(13)
_cell_length_c                   11.149(2)
_cell_angle_alpha                80.680(3)
_cell_angle_beta                 89.072(3)
_cell_angle_gamma                84.658(16)
_cell_volume                     675.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10604
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.611
_cell_measurement_theta_min      1.851
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10604
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.611
_diffrn_reflns_theta_min         1.851
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker-AXS SMART APEXII diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2561
_reflns_number_total             3091
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1672P)²+0.0736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2251
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C4(H4)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1 S 0.26172(10) -0.01427(6) 0.70888(5) 0.0626(3) Uani 1 1 d . . . . .
N1 N 0.2294(2) 0.30442(18) 0.63037(14) 0.0414(4) Uani 1 1 d . . . . .
N2 N 0.2421(2) 0.44230(18) 0.58476(14) 0.0402(4) Uani 1 1 d . . . . .
N3 N 0.2679(2) 0.6020(2) 0.27779(16) 0.0515(5) Uani 1 1 d . . . . .
N4 N 0.2569(3) 0.4551(2) 0.25971(17) 0.0561(5) Uani 1 1 d . . . . .
C7 C 0.2489(2) 0.4704(2) 0.45926(16) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.2255(3) 0.2747(2) 0.75936(17) 0.0395(4) Uani 1 1 d . . . . .
C8 C 0.2629(3) 0.6180(2) 0.39480(18) 0.0456(5) Uani 1 1 d . . . . .
C10 C 0.2451(3) 0.3734(2) 0.36981(18) 0.0470(5) Uani 1 1 d . . . . .
C2 C 0.2404(3) 0.1187(2) 0.81031(17) 0.0426(4) Uani 1 1 d . . . . .
C6 C 0.2065(3) 0.3863(3) 0.8336(2) 0.0519(5) Uani 1 1 d . . . . .
H6 H 0.193704 0.489518 0.799282 0.062 Uiso 1 1 calc R . . . .
C3 C 0.2408(4) 0.0793(3) 0.9364(2) 0.0572(6) Uani 1 1 d . . . . .
H3 H 0.252554 -0.023488 0.971894 0.069 Uiso 1 1 calc R . . . .
C11 C 0.2303(4) 0.2047(3) 0.3836(2) 0.0628(6) Uani 1 1 d . . . . .
H11A H 0.236274 0.173605 0.304934 0.094 Uiso 1 1 calc GR . . . .
H11B H 0.109977 0.180623 0.421989 0.094 Uiso 1 1 calc GR . . . .
H11C H 0.335285 0.151245 0.432705 0.094 Uiso 1 1 calc GR . . . .
C5 C 0.2064(4) 0.3445(3) 0.9590(2) 0.0644(6) Uani 1 1 d . . . . .
H5 H 0.194628 0.419444 1.008802 0.077 Uiso 1 1 calc R . . . .
C13 C 0.2702(4) 0.7659(3) 0.4392(3) 0.0617(6) Uani 1 1 d . . . . .
H13A H 0.377481 0.816723 0.402412 0.093 Uiso 1 1 calc GR . . . .
H13B H 0.285382 0.747272 0.525972 0.093 Uiso 1 1 calc GR . . . .
H13C H 0.152455 0.829501 0.418179 0.093 Uiso 1 1 calc GR . . . .
C4 C 0.2239(4) 0.1923(3) 1.0092(2) 0.0664(7) Uani 1 1 d . . . . .
H4 H 0.224380 0.164626 1.093273 0.080 Uiso 1 1 calc R . . . .
C14 C 0.2776(4) 0.7216(3) 0.1720(2) 0.0657(7) Uani 1 1 d . . . . .
H14A H 0.149519 0.765921 0.149393 0.099 Uiso 1 1 calc GR . . . .
H14B H 0.336647 0.677843 0.105506 0.099 Uiso 1 1 calc GR . . . .
H14C H 0.353059 0.799684 0.191297 0.099 Uiso 1 1 calc GR . . . .
C12 C 0.2887(5) -0.1958(3) 0.8077(3) 0.0834(9) Uani 1 1 d . . . . .
H12A H 0.398610 -0.199385 0.859395 0.125 Uiso 1 1 calc GR . . . .
H12B H 0.307319 -0.276799 0.759843 0.125 Uiso 1 1 calc GR . . . .
H12C H 0.174722 -0.208406 0.856590 0.125 Uiso 1 1 calc GR . . . .


_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 C2 1.757(2) . ?
S1 C12 1.794(3) . ?
N1 N2 1.257(2) . ?
N1 C1 1.420(2) . ?
N2 C7 1.382(2) . ?
N3 N4 1.360(3) . ?
N3 C8 1.334(3) . ?
N3 C14 1.458(3) . ?
N4 C10 1.326(3) . ?
C7 C8 1.399(3) . ?
C7 C10 1.420(3) . ?
C1 C2 1.403(3) . ?
C1 C6 1.386(3) . ?
C8 C13 1.481(3) . ?
C10 C11 1.493(3) . ?
C2 C3 1.393(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.387(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.370(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C4 H4 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C2 S1 C12 103.27(12) . . ?
N2 N1 C1 114.96(16) . . ?
N1 N2 C7 114.77(16) . . ?
N4 N3 C14 118.6(2) . . ?
C8 N3 N4 113.48(17) . . ?
C8 N3 C14 127.9(2) . . ?
C10 N4 N3 105.48(18) . . ?
N2 C7 C8 121.70(17) . . ?
N2 C7 C10 132.66(17) . . ?
C8 C7 C10 105.64(17) . . ?
C2 C1 N1 114.82(17) . . ?
C6 C1 N1 124.87(18) . . ?
C6 C1 C2 120.31(18) . . ?
N3 C8 C7 105.40(17) . . ?
N3 C8 C13 124.39(19) . . ?
C7 C8 C13 130.21(19) . . ?
N4 C10 C7 110.00(19) . . ?
N4 C10 C11 119.7(2) . . ?
C7 C10 C11 130.27(19) . . ?
C1 C2 S1 117.00(15) . . ?
C3 C2 S1 124.41(17) . . ?
C3 C2 C1 118.6(2) . . ?
C1 C6 H6 119.9 . . ?
C1 C6 C5 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
S1 C2 C3 C4 179.78(18) . . . . ?
N1 N2 C7 C8 179.95(15) . . . . ?
N1 N2 C7 C10 -0.3(3) . . . . ?
N1 C1 C2 S1 0.1(2) . . . . ?
N1 C1 C2 C3 179.02(17) . . . . ?
N1 C1 C6 C5 -179.3(2) . . . . ?
N2 N1 C1 C2 -170.93(16) . . . . ?
N2 N1 C1 C6 9.8(3) . . . . ?
N2 C7 C8 N3 179.41(16) . . . . ?
N2 C7 C8 C13 -1.0(3) . . . . ?
N2 C7 C10 N4 -179.49(18) . . . . ?
N2 C7 C10 C11 0.6(4) . . . . ?
N3 N4 C10 C7 -0.1(2) . . . . ?
N3 N4 C10 C11 179.8(2) . . . . ?
N4 N3 C8 C7 0.4(2) . . . . ?
N4 N3 C8 C13 -179.25(19) . . . . ?
C1 N1 N2 C7 179.01(14) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C6 C5 C4 -0.5(4) . . . . ?
C8 N3 N4 C10 -0.2(2) . . . . ?
C8 C7 C10 N4 0.3(2) . . . . ?
C8 C7 C10 C11 -179.6(2) . . . . ?
C10 C7 C8 N3 -0.4(2) . . . . ?
C10 C7 C8 C13 179.2(2) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C6 C1 C2 S1 179.40(15) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C14 N3 N4 C10 -178.47(17) . . . . ?
C14 N3 C8 C7 178.47(18) . . . . ?
C14 N3 C8 C13 -1.2(3) . . . . ?
C12 S1 C2 C1 177.26(17) . . . . ?
C12 S1 C2 C3 -1.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol-Diethyl ether'
_chemical_properties_physical    Photo-sensitive
