# 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 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_csr-45
_database_code_depnum_ccdc_archive 'CCDC 1974743'
loop_
_audit_author_name
_audit_author_address
'Ramendra Pratap' 'University of Delhi'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_audit_creation_date             2019-09-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H19 N3 O S'
_chemical_formula_sum            'C18 H19 N3 O S'
_chemical_formula_weight         325.42
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.5585(6)
_cell_length_b                   8.9403(6)
_cell_length_c                   11.5304(7)
_cell_angle_alpha                83.453(6)
_cell_angle_beta                 70.241(6)
_cell_angle_gamma                78.827(6)
_cell_volume                     813.45(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      3.64
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10130
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.64
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2524
_reflns_number_total             2865
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.2862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1179
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C00L-C00M
 1.54 with sigma of 0.02
 C00L-C00G = C00G-C00M
 1.54 with sigma of 0.02
 N004-H004
 0.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00G(H00D,H00F), C00J(H00G,H00J), C00K(H00K,H00L), C00L(H00M,
 H00N), C00M(H00O,H00P), C00N(H00Q,H00R)
3.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C00C(H00C), C00E(H00E), C00H(H00H), C00I(H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.10668(8) 0.51504(8) 0.70931(6) 0.0436(2) Uani 1 d . . .
O1 O 0.3349(3) 0.7151(3) 0.02219(18) 0.0562(6) Uani 1 d . . .
N3 N 0.3918(2) 0.7713(2) 0.23986(18) 0.0345(5) Uani 1 d . . .
N2 N 0.4970(3) 0.7527(3) 0.69781(19) 0.0428(6) Uani 1 d . . D
H8 H 0.4248 0.7209 0.7636 0.051 Uiso 1 calc . . DR
N1 N 0.7740(3) 0.8968(3) 0.1672(2) 0.0502(6) Uani 1 d . . .
C10 C 0.1836(3) 0.6827(3) 0.6949(2) 0.0328(5) Uani 1 d . . .
C2 C 0.5883(3) 0.8012(3) 0.4773(2) 0.0309(5) Uani 1 d . . .
C3 C 0.4673(3) 0.7593(3) 0.5872(2) 0.0310(5) Uani 1 d . . .
C6 C 0.4107(3) 0.7634(3) 0.3580(2) 0.0319(5) Uani 1 d . . .
C4 C 0.3172(3) 0.7223(3) 0.5815(2) 0.0318(5) Uani 1 d . . .
C1 C 0.5564(3) 0.8048(3) 0.3662(2) 0.0305(5) Uani 1 d . . .
C5 C 0.2932(3) 0.7226(3) 0.4674(2) 0.0342(6) Uani 1 d . . .
H1 H 0.1953 0.6945 0.4650 0.041 Uiso 1 calc . . R
C18 C 0.6772(3) 0.8564(3) 0.2549(2) 0.0342(6) Uani 1 d . . .
C11 C 0.1002(3) 0.7657(3) 0.7991(2) 0.0428(6) Uani 1 d . . .
H9 H 0.1223 0.8600 0.8101 0.051 Uiso 1 calc . . R
C17 C 0.4989(3) 0.6493(3) 0.1602(2) 0.0403(6) Uani 1 d . . .
H19 H 0.4561 0.5542 0.1879 0.048 Uiso 1 calc . . R
H18 H 0.6127 0.6352 0.1634 0.048 Uiso 1 calc . . R
C7 C 0.7484(3) 0.8426(3) 0.4818(2) 0.0383(6) Uani 1 d . . D
H2 H 0.8398 0.8107 0.4077 0.046 Uiso 1 calc . . R
H3 H 0.7355 0.9526 0.4838 0.046 Uiso 1 calc . . R
C13 C -0.0337(3) 0.5550(4) 0.8512(3) 0.0471(7) Uani 1 d . . .
H11 H -0.1087 0.4915 0.8984 0.057 Uiso 1 calc . . R
C12 C -0.0230(3) 0.6888(4) 0.8867(2) 0.0508(7) Uani 1 d . . .
H10 H -0.0904 0.7280 0.9622 0.061 Uiso 1 calc . . R
C14 C 0.2218(3) 0.7926(4) 0.2340(2) 0.0474(7) Uani 1 d . . .
H12 H 0.1510 0.8747 0.2854 0.057 Uiso 1 calc . . R
H13 H 0.1743 0.6999 0.2640 0.057 Uiso 1 calc . . R
C16 C 0.4992(4) 0.6934(4) 0.0305(2) 0.0474(7) Uani 1 d . . .
H17 H 0.5455 0.7869 0.0027 0.057 Uiso 1 calc . . R
H16 H 0.5708 0.6140 -0.0235 0.057 Uiso 1 calc . . R
C8 C 0.7915(3) 0.7685(4) 0.5927(3) 0.0536(8) Uani 1 d . . D
H4 H 0.8252 0.6594 0.5833 0.064 Uiso 1 calc . . R
H5 H 0.8855 0.8085 0.5994 0.064 Uiso 1 calc . . R
C9 C 0.6449(4) 0.7973(4) 0.7072(3) 0.0511(7) Uani 1 d . . D
H6 H 0.6727 0.7407 0.7765 0.061 Uiso 1 calc . . R
H7 H 0.6216 0.9051 0.7227 0.061 Uiso 1 calc . . R
C15 C 0.2290(4) 0.8312(4) 0.1010(3) 0.0581(8) Uani 1 d . . .
H15 H 0.1163 0.8444 0.0958 0.070 Uiso 1 calc . . R
H14 H 0.2707 0.9269 0.0734 0.070 Uiso 1 calc . . R


_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 C10 1.720(2) . ?
S1 C13 1.699(3) . ?
O1 C16 1.416(3) . ?
O1 C15 1.420(4) . ?
N3 C6 1.417(3) . ?
N3 C17 1.465(3) . ?
N3 C14 1.454(3) . ?
N2 H8 0.8600 . ?
N2 C3 1.375(3) . ?
N2 C9 1.439(3) . ?
N1 C18 1.142(3) . ?
C10 C4 1.478(3) . ?
C10 C11 1.387(4) . ?
C2 C3 1.405(3) . ?
C2 C1 1.394(3) . ?
C2 C7 1.505(3) . ?
C3 C4 1.411(3) . ?
C6 C1 1.402(3) . ?
C6 C5 1.384(3) . ?
C4 C5 1.397(3) . ?
C1 C18 1.443(3) . ?
C5 H1 0.9300 . ?
C11 H9 0.9300 . ?
C11 C12 1.417(4) . ?
C17 H19 0.9700 . ?
C17 H18 0.9700 . ?
C17 C16 1.502(4) . ?
C7 H2 0.9700 . ?
C7 H3 0.9700 . ?
C7 C8 1.498(4) . ?
C13 H11 0.9300 . ?
C13 C12 1.337(4) . ?
C12 H10 0.9300 . ?
C14 H12 0.9700 . ?
C14 H13 0.9700 . ?
C14 C15 1.516(4) . ?
C16 H17 0.9700 . ?
C16 H16 0.9700 . ?
C8 H4 0.9700 . ?
C8 H5 0.9700 . ?
C8 C9 1.488(4) . ?
C9 H6 0.9700 . ?
C9 H7 0.9700 . ?
C15 H15 0.9700 . ?
C15 H14 0.9700 . ?

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
C13 S1 C10 92.50(13) . . ?
C16 O1 C15 109.7(2) . . ?
C6 N3 C17 114.57(19) . . ?
C6 N3 C14 117.70(19) . . ?
C14 N3 C17 109.72(19) . . ?
C3 N2 H8 118.9 . . ?
C3 N2 C9 122.2(2) . . ?
C9 N2 H8 118.9 . . ?
C4 C10 S1 120.59(18) . . ?
C11 C10 S1 110.35(18) . . ?
C11 C10 C4 129.0(2) . . ?
C3 C2 C7 119.7(2) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 C7 121.4(2) . . ?
N2 C3 C2 120.1(2) . . ?
N2 C3 C4 121.0(2) . . ?
C2 C3 C4 118.9(2) . . ?
C1 C6 N3 118.0(2) . . ?
C5 C6 N3 125.0(2) . . ?
C5 C6 C1 117.0(2) . . ?
C3 C4 C10 120.9(2) . . ?
C5 C4 C10 119.0(2) . . ?
C5 C4 C3 120.1(2) . . ?
C2 C1 C6 123.0(2) . . ?
C2 C1 C18 118.4(2) . . ?
C6 C1 C18 118.6(2) . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H1 119.0 . . ?
C4 C5 H1 119.0 . . ?
N1 C18 C1 179.4(3) . . ?
C10 C11 H9 124.3 . . ?
C10 C11 C12 111.5(2) . . ?
C12 C11 H9 124.3 . . ?
N3 C17 H19 110.0 . . ?
N3 C17 H18 110.0 . . ?
N3 C17 C16 108.5(2) . . ?
H19 C17 H18 108.4 . . ?
C16 C17 H19 110.0 . . ?
C16 C17 H18 110.0 . . ?
C2 C7 H2 109.3 . . ?
C2 C7 H3 109.3 . . ?
H2 C7 H3 108.0 . . ?
C8 C7 C2 111.5(2) . . ?
C8 C7 H2 109.3 . . ?
C8 C7 H3 109.3 . . ?
S1 C13 H11 124.2 . . ?
C12 C13 S1 111.7(2) . . ?
C12 C13 H11 124.2 . . ?
C11 C12 H10 123.0 . . ?
C13 C12 C11 114.0(2) . . ?
C13 C12 H10 123.0 . . ?
N3 C14 H12 110.0 . . ?
N3 C14 H13 110.0 . . ?
N3 C14 C15 108.6(2) . . ?
H12 C14 H13 108.4 . . ?
C15 C14 H12 110.0 . . ?
C15 C14 H13 110.0 . . ?
O1 C16 C17 111.6(2) . . ?
O1 C16 H17 109.3 . . ?
O1 C16 H16 109.3 . . ?
C17 C16 H17 109.3 . . ?
C17 C16 H16 109.3 . . ?
H17 C16 H16 108.0 . . ?
C7 C8 H4 109.5 . . ?
C7 C8 H5 109.5 . . ?
H4 C8 H5 108.1 . . ?
C9 C8 C7 110.9(2) . . ?
C9 C8 H4 109.5 . . ?
C9 C8 H5 109.5 . . ?
N2 C9 C8 111.8(2) . . ?
N2 C9 H6 109.3 . . ?
N2 C9 H7 109.3 . . ?
C8 C9 H6 109.3 . . ?
C8 C9 H7 109.3 . . ?
H6 C9 H7 107.9 . . ?
O1 C15 C14 111.7(3) . . ?
O1 C15 H15 109.3 . . ?
O1 C15 H14 109.3 . . ?
C14 C15 H15 109.3 . . ?
C14 C15 H14 109.3 . . ?
H15 C15 H14 107.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM and Hexane'
