# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc26fjmt
_database_code_depnum_ccdc_archive 'CCDC 2038796'
loop_
_audit_author_name
_audit_author_address
'Arijit Saha'
;Department of Chemistry, Pondicherry University
India
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2022-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-10-15
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C11 H11 N3 O S)'
_chemical_formula_sum            'C22 H22 N6 O2 S2'
_chemical_formula_weight         466.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H16 O2 N2'
_chemical_oxdiff_usercomment     ?
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                   8.6009(5)
_cell_length_b                   10.6365(7)
_cell_length_c                   13.6233(9)
_cell_angle_alpha                95.201(5)
_cell_angle_beta                 95.934(5)
_cell_angle_gamma                107.575(5)
_cell_volume                     1171.95(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4261
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.3789
_cell_measurement_theta_min      3.1174
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12789
_diffrn_reflns_theta_full        29.44
_diffrn_reflns_theta_max         29.44
_diffrn_reflns_theta_min         3.12
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9975
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -99.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00    9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -99.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   37.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00   45.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -37.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00  -32.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  178.0000  120.0000 61

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   23.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   32.00   96.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835 -178.0000   60.0000 64
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0659723000
_diffrn_orient_matrix_UB_12      0.0251355000
_diffrn_orient_matrix_UB_13      -0.0274043000
_diffrn_orient_matrix_UB_21      0.0514223000
_diffrn_orient_matrix_UB_22      0.0332202000
_diffrn_orient_matrix_UB_23      0.0447613000
_diffrn_orient_matrix_UB_31      0.0251285000
_diffrn_orient_matrix_UB_32      -0.0569201000
_diffrn_orient_matrix_UB_33      0.0056156000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3591
_reflns_number_total             5520
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1023
_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, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N6(H6), C9(H9), C13(H13), C19(H19), C20(H20), C24(H24), C26(H26),
 C27(H27), C28(H28), C30(H30), C31(H31)
2.c X=CH2 refined with riding coordinates:
 N11(H11A,H11B), N14(H14A,H14B)
2.d :
 C25(H25), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.47214(5) 0.82581(4) -0.02329(4) 0.04222(14) Uani 1 d . . .
S2 S -0.04954(6) -0.26846(5) 1.01660(4) 0.04921(15) Uani 1 d . . .
N3 N 0.52509(17) 0.55091(13) 0.13471(11) 0.0377(3) Uani 1 d . . .
N4 N 0.11550(16) -0.11195(13) 0.89897(11) 0.0380(3) Uani 1 d . . .
H4 H 0.1987 -0.1354 0.9206 0.046 Uiso 1 calc . . R
N5 N 0.12907(16) -0.02562(13) 0.82887(10) 0.0367(3) Uani 1 d . . .
N6 N 0.55593(16) 0.65345(13) 0.07797(10) 0.0386(3) Uani 1 d . . .
H6 H 0.6554 0.6941 0.0692 0.046 Uiso 1 calc . . R
O7 O 0.90873(16) 0.43986(14) 0.23054(11) 0.0595(4) Uani 1 d . . .
O8 O 0.57597(15) 0.12636(13) 0.75310(10) 0.0530(3) Uani 1 d . . .
C9 C 0.2707(2) 0.01888(15) 0.80272(13) 0.0357(4) Uani 1 d . . .
H9 H 0.3573 -0.0072 0.8311 0.043 Uiso 1 calc . . R
C10 C 0.2986(2) 0.11072(16) 0.72843(13) 0.0359(4) Uani 1 d . . .
N11 N -0.14899(17) -0.11743(15) 0.89806(12) 0.0529(4) Uani 1 d . . .
H11A H -0.1336 -0.0622 0.8549 0.064 Uiso 1 calc . . R
H11B H -0.2436 -0.1453 0.9181 0.064 Uiso 1 calc . . R
C12 C -0.0281(2) -0.15912(15) 0.93324(13) 0.0358(4) Uani 1 d . . .
C13 C 0.6512(2) 0.52572(16) 0.17401(13) 0.0391(4) Uani 1 d . . .
H13 H 0.7554 0.5743 0.1618 0.047 Uiso 1 calc . . R
N14 N 0.28149(17) 0.61637(14) 0.04474(12) 0.0494(4) Uani 1 d . . .
H14A H 0.2673 0.5480 0.0761 0.059 Uiso 1 calc . . R
H14B H 0.1977 0.6363 0.0190 0.059 Uiso 1 calc . . R
C15 C 0.6336(2) 0.42126(15) 0.23801(13) 0.0363(4) Uani 1 d . . .
C16 C 0.7659(2) 0.37765(16) 0.26683(13) 0.0399(4) Uani 1 d . . .
C17 C 0.4561(2) 0.16479(16) 0.70311(13) 0.0391(4) Uani 1 d . . .
C18 C 1.1202(2) 0.45878(19) 0.36488(17) 0.0505(5) Uani 1 d . . .
C19 C 0.1723(2) 0.14887(18) 0.68239(15) 0.0499(5) Uani 1 d . . .
H19 H 0.0664 0.1141 0.6983 0.060 Uiso 1 calc . . R
C20 C 0.4828(2) 0.25187(17) 0.63279(15) 0.0502(5) Uani 1 d . . .
H20 H 0.5875 0.2859 0.6150 0.060 Uiso 1 calc . . R
C21 C 0.7467(2) 0.1024(2) 0.63025(18) 0.0532(5) Uani 1 d . . .
C22 C 1.0531(2) 0.4075(2) 0.26168(16) 0.0588(6) Uani 1 d . . .
H22A H 1.1358 0.4435 0.2196 0.071 Uiso 1 calc . . R
H22B H 1.0276 0.3116 0.2530 0.071 Uiso 1 calc . . R
C23 C 0.4314(2) 0.69056(15) 0.03603(13) 0.0353(4) Uani 1 d . . .
C24 C 0.5984(3) 0.21842(18) 0.35542(15) 0.0568(5) Uani 1 d . . .
H24 H 0.5864 0.1496 0.3944 0.068 Uiso 1 calc . . R
C25 C 0.7550(3) 0.0469(2) 0.5553(2) 0.0709(7) Uani 1 d . . .
H25 H 0.7616 0.0021 0.4948 0.085 Uiso 1 calc . . R
C26 C 0.3546(3) 0.28795(19) 0.58931(16) 0.0574(5) Uani 1 d . . .
H26 H 0.3732 0.3477 0.5428 0.069 Uiso 1 calc . . R
C27 C 0.2000(3) 0.2371(2) 0.61356(16) 0.0609(6) Uani 1 d . . .
H27 H 0.1136 0.2621 0.5836 0.073 Uiso 1 calc . . R
C28 C 0.4851(2) 0.36048(19) 0.27012(15) 0.0522(5) Uani 1 d . . .
H28 H 0.3951 0.3887 0.2517 0.063 Uiso 1 calc . . R
C29 C 0.7373(2) 0.1699(2) 0.72638(15) 0.0550(5) Uani 1 d . . .
H29A H 0.8139 0.1531 0.7770 0.066 Uiso 1 calc . . R
H29B H 0.7696 0.2650 0.7238 0.066 Uiso 1 calc . . R
C30 C 0.7483(2) 0.27715(18) 0.32591(15) 0.0503(5) Uani 1 d . . .
H30 H 0.8379 0.2492 0.3458 0.060 Uiso 1 calc . . R
C31 C 0.4667(3) 0.2599(2) 0.32826(16) 0.0603(6) Uani 1 d . . .
H31 H 0.3655 0.2204 0.3490 0.072 Uiso 1 calc . . R
C32 C 1.1729(3) 0.5000(2) 0.44638(19) 0.0679(6) Uani 1 d . . .
H32 H 1.2155 0.5334 0.5124 0.082 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 C23 1.6764(17) . ?
S2 C12 1.6821(18) . ?
N3 N6 1.3703(18) . ?
N3 C13 1.271(2) . ?
N4 N5 1.3733(18) . ?
N4 C12 1.335(2) . ?
N5 C9 1.268(2) . ?
N6 C23 1.341(2) . ?
O7 C16 1.373(2) . ?
O7 C22 1.420(2) . ?
O8 C17 1.361(2) . ?
O8 C29 1.421(2) . ?
C9 C10 1.457(2) . ?
C10 C17 1.396(2) . ?
C10 C19 1.382(2) . ?
N11 C12 1.312(2) . ?
C13 C15 1.456(2) . ?
N14 C23 1.317(2) . ?
C15 C16 1.387(2) . ?
C15 C28 1.381(2) . ?
C16 C30 1.377(2) . ?
C17 C20 1.381(2) . ?
C18 C22 1.453(3) . ?
C18 C32 1.148(3) . ?
C19 C27 1.374(3) . ?
C20 C26 1.370(3) . ?
C21 C25 1.152(3) . ?
C21 C29 1.457(3) . ?
C24 C30 1.371(3) . ?
C24 C31 1.364(3) . ?
C26 C27 1.363(3) . ?
C28 C31 1.369(3) . ?

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 N3 N6 115.64(14) . . ?
C12 N4 N5 119.41(14) . . ?
C9 N5 N4 115.80(14) . . ?
C23 N6 N3 120.17(14) . . ?
C16 O7 C22 118.70(15) . . ?
C17 O8 C29 118.37(14) . . ?
N5 C9 C10 120.29(15) . . ?
C17 C10 C9 120.34(15) . . ?
C19 C10 C9 121.66(15) . . ?
C19 C10 C17 117.99(16) . . ?
N4 C12 S2 120.33(13) . . ?
N11 C12 S2 122.71(13) . . ?
N11 C12 N4 116.96(16) . . ?
N3 C13 C15 120.42(16) . . ?
C16 C15 C13 120.51(16) . . ?
C28 C15 C13 121.56(16) . . ?
C28 C15 C16 117.91(16) . . ?
O7 C16 C15 115.03(15) . . ?
O7 C16 C30 124.48(16) . . ?
C30 C16 C15 120.48(17) . . ?
O8 C17 C10 115.18(15) . . ?
O8 C17 C20 124.37(16) . . ?
C20 C17 C10 120.45(17) . . ?
C32 C18 C22 179.5(2) . . ?
C27 C19 C10 121.31(18) . . ?
C26 C20 C17 119.79(18) . . ?
C25 C21 C29 178.5(2) . . ?
O7 C22 C18 112.78(16) . . ?
N6 C23 S1 119.67(12) . . ?
N14 C23 S1 123.69(13) . . ?
N14 C23 N6 116.64(15) . . ?
C31 C24 C30 120.72(18) . . ?
C27 C26 C20 120.69(18) . . ?
C26 C27 C19 119.76(19) . . ?
C31 C28 C15 121.84(18) . . ?
O8 C29 C21 111.78(16) . . ?
C24 C30 C16 119.83(18) . . ?
C24 C31 C28 119.2(2) . . ?

_olex2_date_sample_data_collection 1566597833.08
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_7
_audit_block_doi                 10.5517/ccdc.csd.cc26fjnv
_database_code_depnum_ccdc_archive 'CCDC 2038797'
loop_
_audit_author_name
_audit_author_address
'Arijit Saha'
;Department of Chemistry, Pondicherry University
India
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2022-03-10 downloaded from the CCDC.
;
_audit_creation_date             2020-10-15
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H14 N4 O S'
_chemical_formula_sum            'C18 H14 N4 O S'
_chemical_formula_weight         334.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H15 N3 O S'
_chemical_oxdiff_usercomment     'YELLOW COLOUR PLATE, 298K, 0.84 0.82 0.16'
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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y, z-1/2'

_cell_length_a                   10.6038(7)
_cell_length_b                   9.9316(7)
_cell_length_c                   16.1177(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.716(7)
_cell_angle_gamma                90.00
_cell_volume                     1693.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3562
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.2989
_cell_measurement_theta_min      3.2530
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9712
_diffrn_reflns_theta_full        29.36
_diffrn_reflns_theta_max         29.36
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9967
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -80.00  -53.00   1.0000   10.2000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -37.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -27.00    2.00   1.0000   10.2000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -57.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   86.00   1.0000   10.2000
omega____ theta____ kappa____ phi______ frames
    -       19.9960   77.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00   45.00   1.0000   10.2000
omega____ theta____ kappa____ phi______ frames
    -       19.9960  -77.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00   79.00   1.0000   10.2000
omega____ theta____ kappa____ phi______ frames
    -       19.9960 -178.0000   60.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0368484000
_diffrn_orient_matrix_UB_12      -0.0543001000
_diffrn_orient_matrix_UB_13      -0.0137143000
_diffrn_orient_matrix_UB_21      0.0438710000
_diffrn_orient_matrix_UB_22      0.0464450000
_diffrn_orient_matrix_UB_23      -0.0150848000
_diffrn_orient_matrix_UB_31      0.0348253000
_diffrn_orient_matrix_UB_32      -0.0010293000
_diffrn_orient_matrix_UB_33      0.0390662000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3176
_reflns_number_total             3990
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.5064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1287
_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.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), N6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.58164(4) 0.78028(6) 0.18303(3) 0.05117(16) Uani 1 d . . .
N1 N 0.34972(12) 0.70149(13) 0.16343(8) 0.0352(3) Uani 1 d . . .
N2 N 0.51193(12) 0.82261(14) 0.34770(8) 0.0402(3) Uani 1 d . . .
C3 C 0.40347(14) 0.68285(16) 0.08790(9) 0.0356(3) Uani 1 d . . .
O4 O 0.49346(14) 0.79949(15) 0.59173(8) 0.0600(4) Uani 1 d . . .
C5 C 0.49763(15) 0.83198(16) 0.42514(10) 0.0375(3) Uani 1 d . . .
H5 H 0.4207 0.8098 0.4462 0.045 Uiso 1 calc . . R
N6 N 0.41042(13) 0.77952(15) 0.29781(9) 0.0438(3) Uani 1 d . . .
H6 H 0.3364 0.7713 0.3160 0.053 Uiso 1 calc . . R
C7 C 0.60366(14) 0.87822(15) 0.48118(10) 0.0377(3) Uani 1 d . . .
C8 C 0.32862(15) 0.62037(16) 0.01813(10) 0.0375(3) Uani 1 d . . .
C9 C 0.43356(14) 0.75060(16) 0.21802(10) 0.0356(3) Uani 1 d . . .
C10 C 0.60010(16) 0.85997(17) 0.56677(11) 0.0434(4) Uani 1 d . . .
C11 C 0.52555(16) 0.7203(2) 0.08722(11) 0.0475(4) Uani 1 d . . .
H11 H 0.5734 0.7146 0.0410 0.057 Uiso 1 calc . . R
C12 C 0.22341(16) 0.54160(17) 0.03170(11) 0.0450(4) Uani 1 d . . .
H12 H 0.1971 0.5323 0.0853 0.054 Uiso 1 calc . . R
C13 C 0.70755(16) 0.94203(19) 0.45105(12) 0.0472(4) Uani 1 d . . .
H13 H 0.7106 0.9559 0.3941 0.057 Uiso 1 calc . . R
C14 C 0.70128(19) 0.9007(2) 0.62010(12) 0.0541(5) Uani 1 d . . .
H14 H 0.7000 0.8858 0.6770 0.065 Uiso 1 calc . . R
C15 C 0.15753(18) 0.47708(19) -0.03344(13) 0.0536(5) Uani 1 d . . .
H15 H 0.0876 0.4245 -0.0232 0.064 Uiso 1 calc . . R
C16 C 0.36373(18) 0.6333(2) -0.06301(11) 0.0505(4) Uani 1 d . . .
H16 H 0.4329 0.6865 -0.0738 0.061 Uiso 1 calc . . R
C17 C 0.80690(17) 0.9854(2) 0.50433(14) 0.0574(5) Uani 1 d . . .
H17 H 0.8756 1.0293 0.4835 0.069 Uiso 1 calc . . R
C18 C 0.80325(19) 0.9633(2) 0.58808(14) 0.0590(5) Uani 1 d . . .
H18 H 0.8707 0.9909 0.6238 0.071 Uiso 1 calc . . R
C19 C 0.1945(2) 0.4900(2) -0.11334(13) 0.0601(5) Uani 1 d . . .
H19 H 0.1501 0.4461 -0.1571 0.072 Uiso 1 calc . . R
C20 C 0.4690(2) 0.8044(2) 0.67717(13) 0.0630(5) Uani 1 d . . .
H20A H 0.3792 0.7917 0.6825 0.076 Uiso 1 calc . . R
H20B H 0.4914 0.8929 0.6988 0.076 Uiso 1 calc . . R
C21 C 0.2974(2) 0.5683(2) -0.12793(12) 0.0612(5) Uani 1 d . . .
H21 H 0.3227 0.5776 -0.1818 0.073 Uiso 1 calc . . R
C22 C 0.5375(2) 0.7042(2) 0.72641(14) 0.0665(6) Uani 1 d . . .
N3 N 0.5915(3) 0.6215(3) 0.76804(19) 0.1258(11) Uani 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 C9 1.7278(16) . ?
S1 C11 1.7243(18) . ?
N1 C3 1.3896(19) . ?
N1 C9 1.3042(19) . ?
N2 C5 1.270(2) . ?
N2 N6 1.3698(18) . ?
C3 C8 1.471(2) . ?
C3 C11 1.348(2) . ?
O4 C10 1.364(2) . ?
O4 C20 1.419(2) . ?
C5 H5 0.9300 . ?
C5 C7 1.469(2) . ?
N6 H6 0.8600 . ?
N6 C9 1.355(2) . ?
C7 C10 1.394(2) . ?
C7 C13 1.386(2) . ?
C8 C12 1.391(2) . ?
C8 C16 1.389(2) . ?
C10 C14 1.391(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C15 1.381(2) . ?
C13 H13 0.9300 . ?
C13 C17 1.384(2) . ?
C14 H14 0.9300 . ?
C14 C18 1.376(3) . ?
C15 H15 0.9300 . ?
C15 C19 1.376(3) . ?
C16 H16 0.9300 . ?
C16 C21 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C21 1.373(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C22 1.439(3) . ?
C21 H21 0.9300 . ?
C22 N3 1.185(3) . ?

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
C11 S1 C9 88.02(8) . . ?
C9 N1 C3 109.91(13) . . ?
C5 N2 N6 117.41(14) . . ?
N1 C3 C8 119.63(13) . . ?
C11 C3 N1 114.77(14) . . ?
C11 C3 C8 125.54(15) . . ?
C10 O4 C20 118.60(15) . . ?
N2 C5 H5 120.3 . . ?
N2 C5 C7 119.44(15) . . ?
C7 C5 H5 120.3 . . ?
N2 N6 H6 122.0 . . ?
C9 N6 N2 116.07(13) . . ?
C9 N6 H6 122.0 . . ?
C10 C7 C5 119.92(15) . . ?
C13 C7 C5 121.43(15) . . ?
C13 C7 C10 118.64(15) . . ?
C12 C8 C3 121.02(14) . . ?
C16 C8 C3 121.11(15) . . ?
C16 C8 C12 117.82(15) . . ?
N1 C9 S1 115.96(12) . . ?
N1 C9 N6 124.19(14) . . ?
N6 C9 S1 119.85(12) . . ?
O4 C10 C7 115.16(14) . . ?
O4 C10 C14 124.54(17) . . ?
C14 C10 C7 120.29(17) . . ?
S1 C11 H11 124.3 . . ?
C3 C11 S1 111.34(13) . . ?
C3 C11 H11 124.3 . . ?
C8 C12 H12 119.6 . . ?
C15 C12 C8 120.84(17) . . ?
C15 C12 H12 119.6 . . ?
C7 C13 H13 119.5 . . ?
C17 C13 C7 121.02(18) . . ?
C17 C13 H13 119.5 . . ?
C10 C14 H14 120.2 . . ?
C18 C14 C10 119.54(18) . . ?
C18 C14 H14 120.2 . . ?
C12 C15 H15 119.7 . . ?
C19 C15 C12 120.52(18) . . ?
C19 C15 H15 119.7 . . ?
C8 C16 H16 119.5 . . ?
C21 C16 C8 121.02(18) . . ?
C21 C16 H16 119.5 . . ?
C13 C17 H17 120.3 . . ?
C18 C17 C13 119.48(19) . . ?
C18 C17 H17 120.3 . . ?
C14 C18 H18 119.5 . . ?
C17 C18 C14 120.99(17) . . ?
C17 C18 H18 119.5 . . ?
C15 C19 H19 120.3 . . ?
C21 C19 C15 119.39(17) . . ?
C21 C19 H19 120.3 . . ?
O4 C20 H20A 108.9 . . ?
O4 C20 H20B 108.9 . . ?
O4 C20 C22 113.2(2) . . ?
H20A C20 H20B 107.8 . . ?
C22 C20 H20A 108.9 . . ?
C22 C20 H20B 108.9 . . ?
C16 C21 H21 119.8 . . ?
C19 C21 C16 120.41(19) . . ?
C19 C21 H21 119.8 . . ?
N3 C22 C20 178.5(3) . . ?

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
N1 C3 C8 C12 -20.9(2) . . . . ?
N1 C3 C8 C16 161.92(16) . . . . ?
N1 C3 C11 S1 0.7(2) . . . . ?
N2 C5 C7 C10 -165.26(15) . . . . ?
N2 C5 C7 C13 15.7(2) . . . . ?
N2 N6 C9 S1 -4.5(2) . . . . ?
N2 N6 C9 N1 176.08(15) . . . . ?
C3 N1 C9 S1 0.86(17) . . . . ?
C3 N1 C9 N6 -179.75(15) . . . . ?
C3 C8 C12 C15 -176.41(15) . . . . ?
C3 C8 C16 C21 176.32(18) . . . . ?
O4 C10 C14 C18 -178.75(18) . . . . ?
O4 C20 C22 N3 -144(12) . . . . ?
C5 N2 N6 C9 -170.18(15) . . . . ?
C5 C7 C10 O4 -0.6(2) . . . . ?
C5 C7 C10 C14 178.57(16) . . . . ?
C5 C7 C13 C17 179.89(16) . . . . ?
N6 N2 C5 C7 -179.78(14) . . . . ?
C7 C10 C14 C18 2.1(3) . . . . ?
C7 C13 C17 C18 0.9(3) . . . . ?
C8 C3 C11 S1 -176.34(13) . . . . ?
C8 C12 C15 C19 -0.3(3) . . . . ?
C8 C16 C21 C19 0.5(3) . . . . ?
C9 S1 C11 C3 -0.18(14) . . . . ?
C9 N1 C3 C8 176.24(14) . . . . ?
C9 N1 C3 C11 -1.0(2) . . . . ?
C10 O4 C20 C22 -81.4(2) . . . . ?
C10 C7 C13 C17 0.9(3) . . . . ?
C10 C14 C18 C17 -0.3(3) . . . . ?
C11 S1 C9 N1 -0.41(14) . . . . ?
C11 S1 C9 N6 -179.83(15) . . . . ?
C11 C3 C8 C12 156.07(18) . . . . ?
C11 C3 C8 C16 -21.2(3) . . . . ?
C12 C8 C16 C21 -1.0(3) . . . . ?
C12 C15 C19 C21 -0.3(3) . . . . ?
C13 C7 C10 O4 178.42(16) . . . . ?
C13 C7 C10 C14 -2.4(2) . . . . ?
C13 C17 C18 C14 -1.2(3) . . . . ?
C15 C19 C21 C16 0.2(3) . . . . ?
C16 C8 C12 C15 0.9(3) . . . . ?
C20 O4 C10 C7 -165.94(16) . . . . ?
C20 O4 C10 C14 14.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

