# 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 2018

####################################################################### 
# 
# 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_shelx_174a_mo
_database_code_depnum_ccdc_archive 'CCDC 1552023'
_audit_update_record             
;
2017-05-24 deposited with the CCDC.
2018-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N3 O2 S'
_chemical_formula_sum            'C24 H23 N3 O2 S'
_chemical_formula_weight         417.51

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'
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'

_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, -y, -z'

_cell_length_a                   7.3601(17)
_cell_length_b                   9.2198(16)
_cell_length_c                   15.8574(17)
_cell_angle_alpha                82.112(12)
_cell_angle_beta                 84.799(15)
_cell_angle_gamma                82.514(17)
_cell_volume                     1053.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_reflns_used    1531
_cell_measurement_theta_min      2.5850
_cell_measurement_theta_max      23.9450

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            10798
_diffrn_reflns_av_unetI/netI     0.1621
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         31.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             5870
_reflns_number_gt                1715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1037P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5870
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2316
_refine_ls_R_factor_gt           0.0905
_refine_ls_wR_factor_ref         0.2920
_refine_ls_wR_factor_gt          0.1957
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.000
_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
H2N H 0.825(6) 0.449(5) 0.214(3) 0.089(15) Uiso 1 1 d . . . . .
H3N H 0.658(5) 0.429(4) 0.021(3) 0.067(12) Uiso 1 1 d . . . . .
C1 C 0.7933(6) 0.5627(5) 0.3315(3) 0.0600(11) Uani 1 1 d . . . . .
C2 C 0.6394(5) 0.5535(4) 0.2834(3) 0.0533(10) Uani 1 1 d . . . . .
C3 C 0.4668(6) 0.5931(4) 0.3137(3) 0.0588(11) Uani 1 1 d . . . . .
H3 H 0.3687 0.5825 0.2829 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4340(5) 0.6504(4) 0.3915(3) 0.0527(10) Uani 1 1 d . . . . .
C5 C 0.2591(6) 0.6905(5) 0.4309(3) 0.0701(12) Uani 1 1 d . . . . .
H5 H 0.1555 0.6819 0.4033 0.084 Uiso 1 1 calc R U . . .
C6 C 0.2368(6) 0.7416(5) 0.5082(3) 0.0685(12) Uani 1 1 d . . . . .
H6 H 0.1185 0.7682 0.5314 0.082 Uiso 1 1 calc R U . . .
C7 C 0.3866(6) 0.7552(5) 0.5536(3) 0.0648(11) Uani 1 1 d . . . . .
C8 C 0.5628(6) 0.7144(5) 0.5160(3) 0.0664(12) Uani 1 1 d . . . . .
H8 H 0.6668 0.7216 0.5437 0.080 Uiso 1 1 calc R U . . .
C9 C 0.5790(5) 0.6637(4) 0.4380(3) 0.0554(10) Uani 1 1 d . . . . .
C10 C 0.5218(8) 0.8059(6) 0.6820(4) 0.0966(17) Uani 1 1 d . . . . .
H10A H 0.4823 0.7976 0.7423 0.116 Uiso 1 1 calc R U . . .
H10B H 0.6124 0.7222 0.6728 0.116 Uiso 1 1 calc R U . . .
C11 C 0.6054(9) 0.9414(6) 0.6576(4) 0.132(2) Uani 1 1 d . . . . .
H11A H 0.6166 0.9626 0.5965 0.198 Uiso 1 1 calc R U . . .
H11B H 0.7250 0.9300 0.6791 0.198 Uiso 1 1 calc R U . . .
H11C H 0.5297 1.0211 0.6812 0.198 Uiso 1 1 calc R U . . .
C12 C 0.1831(7) 0.8608(5) 0.6681(3) 0.0827(15) Uani 1 1 d . . . . .
H12A H 0.1871 0.8560 0.7294 0.099 Uiso 1 1 calc R U . . .
H12B H 0.0928 0.7987 0.6578 0.099 Uiso 1 1 calc R U . . .
C13 C 0.1212(8) 1.0173(6) 0.6322(4) 0.117(2) Uani 1 1 d . . . . .
H13A H 0.2086 1.0801 0.6428 0.175 Uiso 1 1 calc R U . . .
H13B H 0.0032 1.0489 0.6591 0.175 Uiso 1 1 calc R U . . .
H13C H 0.1121 1.0227 0.5718 0.175 Uiso 1 1 calc R U . . .
C14 C 0.6197(5) 0.5009(4) 0.1353(3) 0.0497(9) Uani 1 1 d . . . . .
C15 C 0.8721(5) 0.3153(4) 0.0903(2) 0.0522(10) Uani 1 1 d . . . . .
C16 C 0.8584(5) 0.1615(4) 0.0963(2) 0.0492(9) Uani 1 1 d . . . . .
C17 C 0.6959(5) 0.1033(4) 0.0855(3) 0.0636(12) Uani 1 1 d . . . . .
H17 H 0.5904 0.1669 0.0728 0.076 Uiso 1 1 calc R U . . .
C18 C 0.6913(6) -0.0446(5) 0.0935(3) 0.0777(15) Uani 1 1 d . . . . .
H18 H 0.5831 -0.0814 0.0857 0.093 Uiso 1 1 calc R U . . .
C19 C 0.8485(7) -0.1425(5) 0.1135(3) 0.0835(16) Uani 1 1 d . . . . .
H19 H 0.8434 -0.2437 0.1204 0.100 Uiso 1 1 calc R U . . .
C20 C 1.0077(6) -0.0895(5) 0.1227(3) 0.0764(14) Uani 1 1 d . . . . .
H20 H 1.1117 -0.1551 0.1350 0.092 Uiso 1 1 calc R U . . .
C21 C 1.0185(5) 0.0635(5) 0.1139(3) 0.0593(11) Uani 1 1 d . . . . .
C22 C 1.1823(6) 0.1193(5) 0.1240(3) 0.0737(14) Uani 1 1 d . . . . .
H22 H 1.2868 0.0542 0.1363 0.088 Uiso 1 1 calc R U . . .
C23 C 1.1911(6) 0.2677(5) 0.1159(3) 0.0780(15) Uani 1 1 d . . . . .
H23 H 1.3014 0.3028 0.1220 0.094 Uiso 1 1 calc R U . . .
C24 C 1.0336(5) 0.3673(5) 0.0984(3) 0.0615(11) Uani 1 1 d . . . . .
H24 H 1.0398 0.4684 0.0924 0.074 Uiso 1 1 calc R U . . .
N1 N 0.3620(6) 0.8021(5) 0.6323(3) 0.0818(12) Uani 1 1 d . . . . .
N2 N 0.6988(5) 0.4886(4) 0.2087(2) 0.0546(9) Uani 1 1 d . . . . .
N3 N 0.7098(4) 0.4177(3) 0.0771(2) 0.0551(9) Uani 1 1 d . . . . .
O1 O 0.7584(4) 0.6221(3) 0.40675(18) 0.0642(8) Uani 1 1 d . . . . .
O2 O 0.9533(4) 0.5231(4) 0.3102(2) 0.0819(10) Uani 1 1 d . . . . .
S1 S 0.42798(13) 0.61227(11) 0.11177(7) 0.0636(4) Uani 1 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
C1 O2 1.218(4) . ?
C1 O1 1.370(5) . ?
C1 C2 1.440(5) . ?
C2 C3 1.340(5) . ?
C2 N2 1.408(5) . ?
C3 C4 1.397(5) . ?
C3 H3 0.9300 . ?
C4 C9 1.378(5) . ?
C4 C5 1.407(5) . ?
C5 C6 1.361(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(6) . ?
C6 H6 0.9300 . ?
C7 N1 1.365(6) . ?
C7 C8 1.404(6) . ?
C8 C9 1.372(5) . ?
C8 H8 0.9300 . ?
C9 O1 1.392(4) . ?
C10 C11 1.453(7) . ?
C10 N1 1.481(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N1 1.454(5) . ?
C12 C13 1.504(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.333(5) . ?
C14 N3 1.354(5) . ?
C14 S1 1.672(4) . ?
C15 C24 1.361(5) . ?
C15 C16 1.425(5) . ?
C15 N3 1.435(4) . ?
C16 C17 1.406(5) . ?
C16 C21 1.413(5) . ?
C17 C18 1.357(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.404(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.353(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.410(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.401(6) . ?
C22 C23 1.366(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.406(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N2 H2N 0.96(4) . ?
N3 H3N 0.99(4) . ?

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
O2 C1 O1 117.1(4) . . ?
O2 C1 C2 125.1(4) . . ?
O1 C1 C2 117.8(4) . . ?
C3 C2 N2 128.2(4) . . ?
C3 C2 C1 121.1(4) . . ?
N2 C2 C1 110.5(3) . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C9 C4 C3 120.1(4) . . ?
C9 C4 C5 114.9(4) . . ?
C3 C4 C5 125.0(4) . . ?
C6 C5 C4 122.0(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 121.9(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
N1 C7 C6 121.2(4) . . ?
N1 C7 C8 121.5(5) . . ?
C6 C7 C8 117.2(4) . . ?
C9 C8 C7 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C4 125.0(4) . . ?
C8 C9 O1 115.0(4) . . ?
C4 C9 O1 119.9(4) . . ?
C11 C10 N1 111.6(5) . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
N1 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 114.1(4) . . ?
N1 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N1 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 N3 114.8(3) . . ?
N2 C14 S1 124.8(3) . . ?
N3 C14 S1 120.3(3) . . ?
C24 C15 C16 121.9(3) . . ?
C24 C15 N3 119.3(4) . . ?
C16 C15 N3 118.8(3) . . ?
C17 C16 C21 119.0(4) . . ?
C17 C16 C15 123.7(3) . . ?
C21 C16 C15 117.3(4) . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 121.2(4) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 121.5(4) . . ?
C22 C21 C16 119.9(4) . . ?
C20 C21 C16 118.6(4) . . ?
C23 C22 C21 121.1(4) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C15 C24 C23 119.7(4) . . ?
C15 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C7 N1 C12 122.4(4) . . ?
C7 N1 C10 120.5(4) . . ?
C12 N1 C10 117.0(4) . . ?
C14 N2 C2 129.7(3) . . ?
C14 N2 H2N 122(3) . . ?
C2 N2 H2N 107(3) . . ?
C14 N3 C15 125.6(4) . . ?
C14 N3 H3N 116(2) . . ?
C15 N3 H3N 118(2) . . ?
C1 O1 C9 120.9(3) . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.072

