# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_khc1002h
_database_code_depnum_ccdc_archive 'CCDC 1477633'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N3 S'
_chemical_formula_sum            'C24 H23 N3 S'
_chemical_formula_weight         385.51

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2893(19)
_cell_length_b                   9.6941(19)
_cell_length_c                   13.155(3)
_cell_angle_alpha                69.00(3)
_cell_angle_beta                 74.34(3)
_cell_angle_gamma                73.14(3)
_cell_volume                     1040.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3658
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7798
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_av_sigmaI/netI    0.0927
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3658
_reflns_number_gt                2448
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1155P)²+0.3923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3658
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2252
_refine_ls_wR_factor_gt          0.1912
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.008
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13045(11) 0.57774(12) 0.02492(9) 0.0554(4) Uani 1 1 d . . .
N1 N 0.2065(3) 0.8661(4) 0.1461(3) 0.0527(8) Uani 1 1 d . . .
N2 N -0.0423(4) 0.7038(5) 0.1846(4) 0.0807(13) Uani 1 1 d . . .
N3 N 0.3950(3) 0.5912(3) -0.1174(3) 0.0487(7) Uani 1 1 d . . .
C1 C -0.2833(6) 1.0698(7) 0.4646(5) 0.0906(16) Uani 1 1 d . . .
H1A H -0.3541 1.0040 0.4908 0.136 Uiso 1 1 calc R . .
H1B H -0.3346 1.1710 0.4302 0.136 Uiso 1 1 calc R . .
H1C H -0.2448 1.0682 0.5259 0.136 Uiso 1 1 calc R . .
C2 C -0.1518(5) 1.0164(5) 0.3811(4) 0.0596(10) Uani 1 1 d . . .
C3 C -0.0333(5) 0.8966(6) 0.4120(4) 0.0717(13) Uani 1 1 d . . .
H3 H -0.0324 0.8491 0.4871 0.086 Uiso 1 1 calc R . .
C4 C -0.1450(5) 1.0853(6) 0.2694(4) 0.0748(13) Uani 1 1 d . . .
H4 H -0.2210 1.1692 0.2450 0.090 Uiso 1 1 calc R . .
C5 C 0.0838(5) 0.8441(5) 0.3367(4) 0.0693(12) Uani 1 1 d . . .
H5 H 0.1628 0.7636 0.3609 0.083 Uiso 1 1 calc R . .
C6 C 0.0834(4) 0.9112(4) 0.2257(3) 0.0493(9) Uani 1 1 d . . .
C7 C -0.0308(5) 1.0348(6) 0.1933(4) 0.0749(13) Uani 1 1 d . . .
H7 H -0.0300 1.0846 0.1182 0.090 Uiso 1 1 calc R . .
C8 C 0.2033(4) 0.7759(4) 0.0964(3) 0.0450(8) Uani 1 1 d . . .
C9 C 0.0780(4) 0.6916(4) 0.1164(3) 0.0504(9) Uani 1 1 d . . .
C10 C -0.1619(7) 0.6239(10) 0.1938(6) 0.116(3) Uani 1 1 d . . .
H10 H -0.1271 0.5674 0.1398 0.139 Uiso 1 1 calc R . .
C11 C -0.3052(12) 0.7350(15) 0.1706(8) 0.183(6) Uani 1 1 d . . .
H11A H -0.2836 0.8136 0.1015 0.219 Uiso 1 1 calc R . .
H11B H -0.3762 0.6852 0.1623 0.219 Uiso 1 1 calc R . .
C12 C -0.3738(12) 0.8017(12) 0.258(2) 0.232(10) Uani 1 1 d . . .
H12A H -0.3066 0.8605 0.2598 0.278 Uiso 1 1 calc R . .
H12B H -0.4692 0.8711 0.2410 0.278 Uiso 1 1 calc R . .
C13 C -0.4037(13) 0.699(2) 0.3626(16) 0.216(8) Uani 1 1 d . . .
H13A H -0.4750 0.6428 0.3635 0.260 Uiso 1 1 calc R . .
H13B H -0.4497 0.7531 0.4170 0.260 Uiso 1 1 calc R . .
C14 C -0.2630(18) 0.5972(18) 0.3901(7) 0.191(6) Uani 1 1 d . . .
H14A H -0.2839 0.5245 0.4626 0.229 Uiso 1 1 calc R . .
H14B H -0.1944 0.6536 0.3932 0.229 Uiso 1 1 calc R . .
C15 C -0.1892(7) 0.5165(7) 0.3075(10) 0.137(4) Uani 1 1 d . . .
H15A H -0.2537 0.4524 0.3096 0.164 Uiso 1 1 calc R . .
H15B H -0.0923 0.4522 0.3258 0.164 Uiso 1 1 calc R . .
C16 C 0.3275(4) 0.7407(4) 0.0083(3) 0.0433(8) Uani 1 1 d . . .
C17 C 0.3046(4) 0.6384(4) -0.0372(3) 0.0456(8) Uani 1 1 d . . .
C18 C 0.5241(4) 0.6502(4) -0.1642(3) 0.0456(8) Uani 1 1 d . . .
C19 C 0.5583(4) 0.7549(4) -0.1252(3) 0.0458(8) Uani 1 1 d . . .
C20 C 0.4556(4) 0.7983(4) -0.0364(3) 0.0477(9) Uani 1 1 d . . .
H20 H 0.4749 0.8654 -0.0086 0.057 Uiso 1 1 calc R . .
C21 C 0.6242(5) 0.6075(5) -0.2538(4) 0.0629(11) Uani 1 1 d . . .
H21 H 0.6032 0.5394 -0.2800 0.076 Uiso 1 1 calc R . .
C22 C 0.7525(5) 0.6654(6) -0.3030(4) 0.0689(12) Uani 1 1 d . . .
H22 H 0.8179 0.6361 -0.3625 0.083 Uiso 1 1 calc R . .
C23 C 0.7875(5) 0.7678(5) -0.2658(4) 0.0661(12) Uani 1 1 d . . .
H23 H 0.8757 0.8056 -0.3001 0.079 Uiso 1 1 calc R . .
C24 C 0.6926(4) 0.8119(5) -0.1796(3) 0.0589(10) Uani 1 1 d . . .
H24 H 0.7160 0.8809 -0.1557 0.071 Uiso 1 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 C17 1.767(4) . ?
S1 C9 1.797(4) . ?
N1 C8 1.275(5) . ?
N1 C6 1.410(5) . ?
N2 C9 1.235(5) . ?
N2 C10 1.486(6) . ?
N3 C17 1.293(5) . ?
N3 C18 1.375(5) . ?
C1 C2 1.511(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.371(7) . ?
C2 C3 1.374(6) . ?
C3 C5 1.372(6) . ?
C3 H3 0.9300 . ?
C4 C7 1.358(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(6) . ?
C7 H7 0.9300 . ?
C8 C16 1.458(5) . ?
C8 C9 1.525(5) . ?
C10 C11 1.475(13) . ?
C10 C15 1.489(12) . ?
C10 H10 0.9800 . ?
C11 C12 1.430(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.390(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.437(17) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.468(14) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C20 1.358(5) . ?
C16 C17 1.416(5) . ?
C18 C21 1.401(5) . ?
C18 C19 1.429(5) . ?
C19 C20 1.403(5) . ?
C19 C24 1.417(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.397(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.354(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C17 S1 C9 92.25(17) . . ?
C8 N1 C6 123.2(3) . . ?
C9 N2 C10 120.1(4) . . ?
C17 N3 C18 116.0(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 C3 116.2(4) . . ?
C4 C2 C1 121.4(4) . . ?
C3 C2 C1 122.4(4) . . ?
C5 C3 C2 122.8(4) . . ?
C5 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C7 C4 C2 122.1(4) . . ?
C7 C4 H4 119.0 . . ?
C2 C4 H4 119.0 . . ?
C6 C5 C3 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C3 C5 H5 120.3 . . ?
C5 C6 C7 118.5(4) . . ?
C5 C6 N1 120.9(4) . . ?
C7 C6 N1 120.2(4) . . ?
C4 C7 C6 120.9(4) . . ?
C4 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C8 C16 121.9(3) . . ?
N1 C8 C9 127.8(3) . . ?
C16 C8 C9 110.4(3) . . ?
N2 C9 C8 124.0(4) . . ?
N2 C9 S1 126.0(3) . . ?
C8 C9 S1 110.0(3) . . ?
C11 C10 N2 109.7(6) . . ?
C11 C10 C15 109.8(5) . . ?
N2 C10 C15 109.6(6) . . ?
C11 C10 H10 109.2 . . ?
N2 C10 H10 109.2 . . ?
C15 C10 H10 109.2 . . ?
C12 C11 C10 111.0(8) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 114.9(10) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 C14 109.3(8) . . ?
C12 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 C15 110.9(8) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C10 111.4(6) . . ?
C14 C15 H15A 109.4 . . ?
C10 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C10 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C20 C16 C17 117.9(3) . . ?
C20 C16 C8 127.9(3) . . ?
C17 C16 C8 114.1(3) . . ?
N3 C17 C16 126.6(3) . . ?
N3 C17 S1 120.1(3) . . ?
C16 C17 S1 113.3(3) . . ?
N3 C18 C21 118.8(3) . . ?
N3 C18 C19 122.2(3) . . ?
C21 C18 C19 119.1(3) . . ?
C20 C19 C24 123.4(4) . . ?
C20 C19 C18 118.3(3) . . ?
C24 C19 C18 118.3(3) . . ?
C16 C20 C19 119.1(3) . . ?
C16 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C18 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C18 C21 H21 119.9 . . ?
C21 C22 C23 121.4(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 119.8(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C19 121.3(4) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?

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
C4 C2 C3 C5 -2.0(8) . . . . ?
C1 C2 C3 C5 177.7(5) . . . . ?
C3 C2 C4 C7 2.4(8) . . . . ?
C1 C2 C4 C7 -177.3(5) . . . . ?
C2 C3 C5 C6 -0.9(8) . . . . ?
C3 C5 C6 C7 3.4(7) . . . . ?
C3 C5 C6 N1 176.1(4) . . . . ?
C8 N1 C6 C5 99.4(5) . . . . ?
C8 N1 C6 C7 -87.9(5) . . . . ?
C2 C4 C7 C6 0.1(8) . . . . ?
C5 C6 C7 C4 -3.0(7) . . . . ?
N1 C6 C7 C4 -175.9(4) . . . . ?
C6 N1 C8 C16 175.1(3) . . . . ?
C6 N1 C8 C9 -4.6(6) . . . . ?
C10 N2 C9 C8 176.5(5) . . . . ?
C10 N2 C9 S1 -2.1(8) . . . . ?
N1 C8 C9 N2 1.6(7) . . . . ?
C16 C8 C9 N2 -178.1(4) . . . . ?
N1 C8 C9 S1 -179.6(3) . . . . ?
C16 C8 C9 S1 0.7(4) . . . . ?
C17 S1 C9 N2 178.1(5) . . . . ?
C17 S1 C9 C8 -0.7(3) . . . . ?
C9 N2 C10 C11 -119.9(7) . . . . ?
C9 N2 C10 C15 119.4(6) . . . . ?
N2 C10 C11 C12 -70.2(9) . . . . ?
C15 C10 C11 C12 50.4(11) . . . . ?
C10 C11 C12 C13 -56.3(14) . . . . ?
C11 C12 C13 C14 59.3(16) . . . . ?
C12 C13 C14 C15 -58.2(15) . . . . ?
C13 C14 C15 C10 56.3(11) . . . . ?
C11 C10 C15 C14 -51.8(9) . . . . ?
N2 C10 C15 C14 68.8(8) . . . . ?
N1 C8 C16 C20 -2.9(6) . . . . ?
C9 C8 C16 C20 176.9(4) . . . . ?
N1 C8 C16 C17 179.9(3) . . . . ?
C9 C8 C16 C17 -0.3(4) . . . . ?
C18 N3 C17 C16 -1.7(5) . . . . ?
C18 N3 C17 S1 176.9(3) . . . . ?
C20 C16 C17 N3 1.0(6) . . . . ?
C8 C16 C17 N3 178.4(3) . . . . ?
C20 C16 C17 S1 -177.7(3) . . . . ?
C8 C16 C17 S1 -0.3(4) . . . . ?
C9 S1 C17 N3 -178.2(3) . . . . ?
C9 S1 C17 C16 0.6(3) . . . . ?
C17 N3 C18 C21 -177.9(3) . . . . ?
C17 N3 C18 C19 1.3(5) . . . . ?
N3 C18 C19 C20 -0.2(5) . . . . ?
C21 C18 C19 C20 179.0(3) . . . . ?
N3 C18 C19 C24 -178.9(3) . . . . ?
C21 C18 C19 C24 0.3(5) . . . . ?
C17 C16 C20 C19 0.3(5) . . . . ?
C8 C16 C20 C19 -176.8(3) . . . . ?
C24 C19 C20 C16 178.1(4) . . . . ?
C18 C19 C20 C16 -0.6(5) . . . . ?
N3 C18 C21 C22 179.2(4) . . . . ?
C19 C18 C21 C22 0.0(6) . . . . ?
C18 C21 C22 C23 0.0(7) . . . . ?
C21 C22 C23 C24 -0.4(7) . . . . ?
C22 C23 C24 C19 0.7(7) . . . . ?
C20 C19 C24 C23 -179.3(4) . . . . ?
C18 C19 C24 C23 -0.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.067
