# 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 2019

####################################################################### 
# 
# 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_gk16
_database_code_depnum_ccdc_archive 'CCDC 1844826'
loop_
_audit_author_name
_audit_author_address
'Krishnaraj Padmavathy'
;Kalasalingam university
India
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-07-23 downloaded from the CCDC.
;
_audit_creation_date             2019-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         'C27 H26 N2 O2 S'
_chemical_formula_sum            'C27 H26 N2 O2 S'
_chemical_formula_weight         442.59
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.5621(5)
_cell_length_b                   19.4912(15)
_cell_length_c                   16.1178(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.666(3)
_cell_angle_gamma                90
_cell_volume                     2348.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    39121
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.09
_exptl_absorpt_coefficient_mu    0.164
_exptl_crystal_colour            'dull whiteish white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.2516
_exptl_crystal_description       plate
_exptl_crystal_F_000             936.8765
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39128
_diffrn_reflns_theta_full        24.9984
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2066
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.4886
_refine_diff_density_min         -0.4516
_refine_diff_density_rms         0.0950
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             9.7456
_refine_ls_goodness_of_fit_ref   1.1596
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.1596
_refine_ls_shift/su_max          0.0113
_refine_ls_shift/su_mean         0.0011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0856P)²+0.3208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.2044
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22a,H22b), C24(H24a,H24b), C23(H23a,H23b), C25(H25a,H25b), C26(H26a,H26b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C8(H8), C13(H13), C17(H17), C5(H5), C1(H1), C2(H2), C18(H18),
 C7(H7), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c)
;
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_refinement_flags_posn
S1 S 0.07811(13) -0.29166(6) 0.38995(7) 0.0640(4) Uani 1.000000 .
N1 N 0.3770(4) 0.08555(17) 0.59608(19) 0.0556(8) Uani 1.000000 .
O2 O -0.0036(4) -0.34483(15) 0.43252(19) 0.0806(9) Uani 1.000000 .
C15 C 0.2359(6) -0.2555(2) 0.5428(3) 0.0659(12) Uani 1.000000 .
O1 O -0.0208(3) -0.25771(15) 0.31915(17) 0.0773(9) Uani 1.000000 .
C12 C 0.2278(5) 0.0946(2) 0.4631(2) 0.0510(10) Uani 1.000000 .
C6 C 0.1746(6) 0.2005(3) 0.3891(3) 0.0725(12) Uani 1.000000 .
H6 H 0.1293(6) 0.2245(3) 0.3407(3) 0.0870(15) Uiso 1.000000 R
N2 N 0.2957(6) -0.2812(2) 0.6043(3) 0.0914(13) Uani 1.000000 .
C3 C 0.2106(5) -0.1002(2) 0.4872(2) 0.0501(10) Uani 1.000000 .
C4 C 0.1784(4) -0.0372(2) 0.4469(2) 0.0532(10) Uani 1.000000 .
H4 H 0.1166(4) -0.0358(2) 0.3925(2) 0.0638(12) Uiso 1.000000 R
C8 C 0.3318(5) 0.2027(2) 0.5300(3) 0.0628(11) Uani 1.000000 .
H8 H 0.3897(5) 0.2267(2) 0.5761(3) 0.0753(13) Uiso 1.000000 R
C13 C 0.1481(5) -0.1613(2) 0.4422(2) 0.0553(10) Uani 1.000000 .
H13 H 0.0891(5) -0.1531(2) 0.3882(2) 0.0664(12) Uiso 1.000000 R
C17 C 0.3377(6) -0.2985(2) 0.2909(3) 0.0693(12) Uani 1.000000 .
H17 H 0.2721(6) -0.2655(2) 0.2577(3) 0.0832(14) Uiso 1.000000 R
C5 C 0.1556(5) 0.1300(2) 0.3911(2) 0.0623(11) Uani 1.000000 .
H5 H 0.0954(5) 0.1066(2) 0.3449(2) 0.0748(13) Uiso 1.000000 R
C1 C 0.3652(5) -0.0420(2) 0.6098(3) 0.0610(11) Uani 1.000000 .
H1 H 0.4280(5) -0.0435(2) 0.6640(3) 0.0732(13) Uiso 1.000000 R
C2 C 0.3054(5) -0.1009(2) 0.5695(3) 0.0612(11) Uani 1.000000 .
H2 H 0.3276(5) -0.1426(2) 0.5970(3) 0.0734(13) Uiso 1.000000 R
C11 C 0.3146(4) 0.1314(2) 0.5315(2) 0.0531(10) Uani 1.000000 .
C14 C 0.1590(5) -0.2280(2) 0.4634(2) 0.0544(10) Uani 1.000000 .
C9 C 0.3311(4) 0.0202(2) 0.5689(2) 0.0519(10) Uani 1.000000 .
C18 C 0.4977(7) -0.3217(3) 0.2708(3) 0.0850(15) Uani 1.000000 .
H18 H 0.5396(7) -0.3051(3) 0.2233(3) 0.1020(18) Uiso 1.000000 R
C10 C 0.2366(4) 0.0233(2) 0.4866(2) 0.0488(9) Uani 1.000000 .
C7 C 0.2600(6) 0.2357(2) 0.4580(3) 0.0737(12) Uani 1.000000 .
H7 H 0.2688(6) 0.2832(2) 0.4554(3) 0.0885(15) Uiso 1.000000 R
C16 C 0.2752(5) -0.3242(2) 0.3602(3) 0.0595(11) Uani 1.000000 .
C22 C 0.4770(5) 0.1049(2) 0.6764(3) 0.0671(12) Uani 1.000000 .
H22a H 0.5493(5) 0.0662(2) 0.6991(3) 0.0805(14) Uiso 1.000000 R
H22b H 0.5575(5) 0.1421(2) 0.6680(3) 0.0805(14) Uiso 1.000000 R
C24 C 0.2416(8) 0.0721(3) 0.7648(3) 0.1088(18) Uani 1.000000 .
H24a H 0.1665(8) 0.0556(3) 0.7147(3) 0.131(2) Uiso 1.000000 R
H24b H 0.3167(8) 0.0342(3) 0.7875(3) 0.131(2) Uiso 1.000000 R
C19 C 0.5947(7) -0.3689(3) 0.3205(4) 0.0960(18) Uani 1.000000 .
H19 H 0.7041(7) -0.3837(3) 0.3074(4) 0.115(2) Uiso 1.000000 R
C20 C 0.5323(7) -0.3953(3) 0.3903(4) 0.0985(16) Uani 1.000000 .
H20 H 0.5985(7) -0.4282(3) 0.4233(4) 0.118(2) Uiso 1.000000 R
C21 C 0.3708(6) -0.3724(2) 0.4109(3) 0.0805(13) Uani 1.000000 .
H21 H 0.3278(6) -0.3894(2) 0.4580(3) 0.0966(16) Uiso 1.000000 R
C23 C 0.3597(7) 0.1272(3) 0.7396(3) 0.0898(15) Uani 1.000000 .
H23a H 0.4356(7) 0.1439(3) 0.7894(3) 0.1078(18) Uiso 1.000000 R
H23b H 0.2854(7) 0.1651(3) 0.7161(3) 0.1078(18) Uiso 1.000000 R
C25 C 0.1271(11) 0.0905(4) 0.8256(5) 0.173(3) Uani 1.000000 .
H25a H 0.2009(11) 0.1022(4) 0.8782(5) 0.207(4) Uiso 1.000000 R
H25b H 0.0581(11) 0.1308(4) 0.8058(5) 0.207(4) Uiso 1.000000 R
C26 C -0.0011(18) 0.0330(6) 0.8411(8) 0.266(8) Uani 1.000000 .
H26a H -0.0596(18) 0.0169(6) 0.7869(8) 0.319(9) Uiso 1.000000 R
H26b H 0.0702(18) -0.0048(6) 0.8671(8) 0.319(9) Uiso 1.000000 R
C27 C -0.1164(19) 0.0449(5) 0.8836(9) 0.277(5) Uani 1.000000 .
H27a H -0.194(10) 0.080(5) 0.857(4) 0.416(8) Uiso 1.000000 GR
H27b H -0.184(11) 0.0039(17) 0.889(7) 0.416(8) Uiso 1.000000 GR
H27c H -0.062(2) 0.060(6) 0.938(3) 0.416(8) Uiso 1.000000 GR


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 O2 1.433(3) . ?
S1 O1 1.429(3) . ?
S1 C14 1.760(4) . ?
S1 C16 1.752(4) . ?
N1 C11 1.399(5) . ?
N1 C9 1.374(4) . ?
N1 C22 1.448(5) . ?
C15 N2 1.141(5) . ?
C15 C14 1.429(6) . ?
C12 C5 1.389(5) . ?
C12 C11 1.394(5) . ?
C12 C10 1.441(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(6) . ?
C6 C7 1.380(6) . ?
C3 C4 1.393(5) . ?
C3 C13 1.436(5) . ?
C3 C2 1.410(5) . ?
C4 H4 0.9300 . ?
C4 C10 1.381(5) . ?
C8 H8 0.9300 . ?
C8 C11 1.395(5) . ?
C8 C7 1.365(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.344(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(6) . ?
C17 C16 1.372(5) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.362(5) . ?
C1 C9 1.385(5) . ?
C2 H2 0.9300 . ?
C9 C10 1.411(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.360(7) . ?
C7 H7 0.9300 . ?
C16 C21 1.376(6) . ?
C22 H22a 0.9700 . ?
C22 H22b 0.9700 . ?
C22 C23 1.512(6) . ?
C24 H24a 0.9700 . ?
C24 H24b 0.9700 . ?
C24 C23 1.491(6) . ?
C24 C25 1.446(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(6) . ?
C21 H21 0.9300 . ?
C23 H23a 0.9700 . ?
C23 H23b 0.9700 . ?
C25 H25a 0.9700 . ?
C25 H25b 0.9700 . ?
C25 C26 1.527(11) . ?
C26 H26a 0.9700 . ?
C26 H26b 0.9700 . ?
C26 C27 1.210(14) . ?
C27 H27a 0.9600 . ?
C27 H27b 0.9600 . ?
C27 H27c 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
O1 S1 O2 120.39(18) . . ?
C14 S1 O2 108.59(18) . . ?
C14 S1 O1 107.31(19) . . ?
C16 S1 O2 108.3(2) . . ?
C16 S1 O1 108.29(19) . . ?
C16 S1 C14 102.46(17) . . ?
C9 N1 C11 108.4(3) . . ?
C22 N1 C11 124.8(3) . . ?
C22 N1 C9 126.8(3) . . ?
C14 C15 N2 176.1(5) . . ?
C11 C12 C5 119.0(4) . . ?
C10 C12 C5 134.0(4) . . ?
C10 C12 C11 107.0(3) . . ?
C5 C6 H6 119.6(3) . . ?
C7 C6 H6 119.6(3) . . ?
C7 C6 C5 120.9(4) . . ?
C13 C3 C4 118.3(3) . . ?
C2 C3 C4 118.3(4) . . ?
C2 C3 C13 123.4(4) . . ?
H4 C4 C3 119.5(2) . . ?
C10 C4 C3 121.1(4) . . ?
C10 C4 H4 119.5(2) . . ?
C11 C8 H8 121.4(2) . . ?
C7 C8 H8 121.4(3) . . ?
C7 C8 C11 117.3(4) . . ?
H13 C13 C3 114.0(2) . . ?
C14 C13 C3 132.1(4) . . ?
C14 C13 H13 114.0(2) . . ?
C18 C17 H17 120.2(3) . . ?
C16 C17 H17 120.2(3) . . ?
C16 C17 C18 119.6(5) . . ?
C6 C5 C12 118.9(4) . . ?
H5 C5 C12 120.6(2) . . ?
H5 C5 C6 120.6(3) . . ?
C2 C1 H1 120.5(2) . . ?
C9 C1 H1 120.5(2) . . ?
C9 C1 C2 119.1(4) . . ?
C1 C2 C3 121.8(4) . . ?
H2 C2 C3 119.1(2) . . ?
H2 C2 C1 119.1(2) . . ?
C12 C11 N1 109.0(3) . . ?
C8 C11 N1 128.9(4) . . ?
C8 C11 C12 122.1(4) . . ?
C15 C14 S1 113.0(3) . . ?
C13 C14 S1 120.6(3) . . ?
C13 C14 C15 126.4(4) . . ?
C1 C9 N1 129.8(4) . . ?
C10 C9 N1 109.2(3) . . ?
C10 C9 C1 121.0(4) . . ?
H18 C18 C17 120.0(3) . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 H18 120.0(3) . . ?
C4 C10 C12 134.8(4) . . ?
C9 C10 C12 106.5(3) . . ?
C9 C10 C4 118.7(4) . . ?
C8 C7 C6 121.8(4) . . ?
H7 C7 C6 119.1(3) . . ?
H7 C7 C8 119.1(3) . . ?
C17 C16 S1 120.1(4) . . ?
C21 C16 S1 118.5(3) . . ?
C21 C16 C17 121.2(4) . . ?
H22a C22 N1 108.9(2) . . ?
H22b C22 N1 108.9(2) . . ?
H22b C22 H22a 107.7 . . ?
C23 C22 N1 113.4(3) . . ?
C23 C22 H22a 108.9(2) . . ?
C23 C22 H22b 108.9(2) . . ?
H24b C24 H24a 107.3 . . ?
C23 C24 H24a 108.1(3) . . ?
C23 C24 H24b 108.1(3) . . ?
C25 C24 H24a 108.1(4) . . ?
C25 C24 H24b 108.1(4) . . ?
C25 C24 C23 116.8(5) . . ?
H19 C19 C18 119.6(3) . . ?
C20 C19 C18 120.7(5) . . ?
C20 C19 H19 119.6(3) . . ?
H20 C20 C19 120.1(3) . . ?
C21 C20 C19 119.7(5) . . ?
C21 C20 H20 120.1(3) . . ?
C20 C21 C16 118.7(5) . . ?
H21 C21 C16 120.6(3) . . ?
H21 C21 C20 120.6(3) . . ?
C24 C23 C22 114.4(4) . . ?
H23a C23 C22 108.7(2) . . ?
H23a C23 C24 108.7(3) . . ?
H23b C23 C22 108.7(2) . . ?
H23b C23 C24 108.7(3) . . ?
H23b C23 H23a 107.6 . . ?
H25a C25 C24 109.0(4) . . ?
H25b C25 C24 109.0(4) . . ?
H25b C25 H25a 107.8 . . ?
C26 C25 C24 112.9(6) . . ?
C26 C25 H25a 109.0(6) . . ?
C26 C25 H25b 109.0(6) . . ?
H26a C26 C25 107.6(6) . . ?
H26b C26 C25 107.6(7) . . ?
H26b C26 H26a 107.1 . . ?
C27 C26 C25 118.8(11) . . ?
C27 C26 H26a 107.6(11) . . ?
C27 C26 H26b 107.6(10) . . ?
H27a C27 C26 109.5 . . ?
H27b C27 C26 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 C26 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
