# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_mo_nj_tdj_118_0m
_database_code_depnum_ccdc_archive 'CCDC 1412186'
_audit_update_record             
;
2015-07-12 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N3 O3 S'
_chemical_formula_weight         397.48

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   ' C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.120(3)
_cell_length_b                   11.7114(16)
_cell_length_c                   16.324(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.222(4)
_cell_angle_gamma                90.00
_cell_volume                     3993.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19981
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4563
_reflns_number_gt                3420
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0523P)²+3.0870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4563
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_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 0.47687(2) 0.26385(4) 1.04529(3) 0.04255(14) Uani 1 1 d . . .
N2 N 0.58482(7) 0.22416(12) 0.86062(10) 0.0438(4) Uani 1 1 d . . .
O1 O 0.43971(6) 0.16254(12) 1.03923(8) 0.0554(4) Uani 1 1 d . . .
N3 N 0.51294(7) 0.25014(11) 0.97256(9) 0.0400(3) Uani 1 1 d . . .
O2 O 0.44614(6) 0.37306(12) 1.02991(9) 0.0566(4) Uani 1 1 d . . .
C16 C 0.53589(8) 0.26697(14) 1.14781(11) 0.0393(4) Uani 1 1 d . . .
C14 C 0.56263(9) 0.33690(14) 0.87672(12) 0.0459(4) Uani 1 1 d . . .
H14A H 0.5217 0.3532 0.8330 0.055 Uiso 1 1 calc R . .
H14B H 0.5929 0.3944 0.8722 0.055 Uiso 1 1 calc R . .
C3 C 0.70530(8) 0.36777(14) 0.84546(11) 0.0403(4) Uani 1 1 d . . .
C17 C 0.55921(9) 0.37042(15) 1.18603(13) 0.0491(4) Uani 1 1 d . . .
H17 H 0.5432 0.4386 1.1580 0.059 Uiso 1 1 calc R . .
C12 C 0.53985(10) 0.13802(14) 0.96391(13) 0.0482(4) Uani 1 1 d . . .
H12A H 0.5118 0.0781 0.9711 0.058 Uiso 1 1 calc R . .
H12B H 0.5813 0.1289 1.0085 0.058 Uiso 1 1 calc R . .
C8 C 0.73099(9) 0.37577(16) 0.93548(12) 0.0489(4) Uani 1 1 d . . .
H8 H 0.7140 0.3330 0.9707 0.059 Uiso 1 1 calc R . .
C13 C 0.55574(9) 0.34261(14) 0.96521(12) 0.0445(4) Uani 1 1 d . . .
H13A H 0.5973 0.3342 1.0096 0.053 Uiso 1 1 calc R . .
H13B H 0.5380 0.4159 0.9732 0.053 Uiso 1 1 calc R . .
N1 N 0.69901(8) 0.41248(15) 0.70899(10) 0.0559(4) Uani 1 1 d . . .
C2 C 0.65550(8) 0.30194(16) 0.78638(12) 0.0440(4) Uani 1 1 d . . .
C11 C 0.54694(10) 0.12919(15) 0.87595(13) 0.0495(5) Uani 1 1 d . . .
H11A H 0.5677 0.0576 0.8715 0.059 Uiso 1 1 calc R . .
H11B H 0.5049 0.1296 0.8319 0.059 Uiso 1 1 calc R . .
O3 O 0.61634(8) 0.11369(12) 0.76977(12) 0.0780(5) Uani 1 1 d . . .
C10 C 0.61746(9) 0.20684(16) 0.80408(13) 0.0467(4) Uani 1 1 d . . .
C18 C 0.60633(9) 0.37144(17) 1.26602(13) 0.0532(5) Uani 1 1 d . . .
H18 H 0.6217 0.4411 1.2919 0.064 Uiso 1 1 calc R . .
C15 C 0.56045(10) 0.16616(15) 1.18932(13) 0.0532(5) Uani 1 1 d . . .
H15 H 0.5451 0.0965 1.1635 0.064 Uiso 1 1 calc R . .
C5 C 0.78359(9) 0.50836(18) 0.83134(15) 0.0582(5) Uani 1 1 d . . .
H5 H 0.8008 0.5522 0.7970 0.070 Uiso 1 1 calc R . .
C4 C 0.73226(8) 0.43551(16) 0.79481(12) 0.0458(4) Uani 1 1 d . . .
C6 C 0.80784(10) 0.51311(19) 0.92003(16) 0.0638(6) Uani 1 1 d . . .
H6 H 0.8424 0.5608 0.9465 0.077 Uiso 1 1 calc R . .
C19 C 0.63112(9) 0.27198(17) 1.30841(12) 0.0493(5) Uani 1 1 d . . .
C1 C 0.65405(10) 0.33190(18) 0.70478(13) 0.0538(5) Uani 1 1 d . . .
H1 H 0.6262 0.3014 0.6537 0.065 Uiso 1 1 calc R . .
C7 C 0.78170(10) 0.44768(19) 0.97141(14) 0.0600(5) Uani 1 1 d . . .
H7 H 0.7991 0.4530 1.0315 0.072 Uiso 1 1 calc R . .
C21 C 0.68257(11) 0.2741(2) 1.39640(14) 0.0724(7) Uani 1 1 d . . .
H21A H 0.7239 0.2695 1.3893 0.109 Uiso 1 1 calc R . .
H21B H 0.6770 0.2104 1.4301 0.109 Uiso 1 1 calc R . .
H21C H 0.6796 0.3439 1.4257 0.109 Uiso 1 1 calc R . .
C20 C 0.60778(10) 0.16931(17) 1.26915(13) 0.0577(5) Uani 1 1 d . . .
H20 H 0.6242 0.1013 1.2970 0.069 Uiso 1 1 calc R . .
C9 C 0.70690(14) 0.4737(3) 0.63555(16) 0.0844(8) Uani 1 1 d . . .
H9A H 0.6795 0.4407 0.5825 0.127 Uiso 1 1 calc R . .
H9B H 0.7506 0.4682 0.6375 0.127 Uiso 1 1 calc R . .
H9C H 0.6958 0.5525 0.6383 0.127 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 O1 1.4283(13) . ?
S1 O2 1.4313(14) . ?
S1 N3 1.6419(15) . ?
S1 C16 1.7514(18) . ?
N2 C10 1.361(2) . ?
N2 C14 1.462(2) . ?
N2 C11 1.463(2) . ?
N3 C12 1.468(2) . ?
N3 C13 1.469(2) . ?
C16 C15 1.380(3) . ?
C16 C17 1.383(2) . ?
C14 C13 1.503(2) . ?
C3 C8 1.393(3) . ?
C3 C4 1.412(2) . ?
C3 C2 1.428(3) . ?
C17 C18 1.377(3) . ?
C12 C11 1.499(2) . ?
C8 C7 1.370(3) . ?
N1 C1 1.356(2) . ?
N1 C4 1.378(2) . ?
N1 C9 1.456(3) . ?
C2 C1 1.367(3) . ?
C2 C10 1.481(2) . ?
O3 C10 1.223(2) . ?
C18 C19 1.373(3) . ?
C15 C20 1.377(3) . ?
C5 C6 1.369(3) . ?
C5 C4 1.388(3) . ?
C6 C7 1.394(3) . ?
C19 C20 1.380(3) . ?
C19 C21 1.511(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
O1 S1 O2 120.07(8) . . ?
O1 S1 N3 105.92(7) . . ?
O2 S1 N3 106.04(8) . . ?
O1 S1 C16 108.33(8) . . ?
O2 S1 C16 108.09(8) . . ?
N3 S1 C16 107.83(8) . . ?
C10 N2 C14 122.73(14) . . ?
C10 N2 C11 117.65(14) . . ?
C14 N2 C11 114.26(14) . . ?
C12 N3 C13 111.04(13) . . ?
C12 N3 S1 117.78(11) . . ?
C13 N3 S1 117.82(11) . . ?
C15 C16 C17 119.99(17) . . ?
C15 C16 S1 120.02(13) . . ?
C17 C16 S1 119.97(14) . . ?
N2 C14 C13 111.04(14) . . ?
C8 C3 C4 118.39(17) . . ?
C8 C3 C2 134.82(17) . . ?
C4 C3 C2 106.77(15) . . ?
C18 C17 C16 119.28(17) . . ?
N3 C12 C11 109.13(14) . . ?
C7 C8 C3 119.01(18) . . ?
N3 C13 C14 108.52(14) . . ?
C1 N1 C4 108.95(15) . . ?
C1 N1 C9 125.84(19) . . ?
C4 N1 C9 124.93(19) . . ?
C1 C2 C3 106.55(16) . . ?
C1 C2 C10 123.41(17) . . ?
C3 C2 C10 129.49(16) . . ?
N2 C11 C12 110.98(15) . . ?
O3 C10 N2 120.55(16) . . ?
O3 C10 C2 120.58(17) . . ?
N2 C10 C2 118.86(15) . . ?
C19 C18 C17 121.50(17) . . ?
C20 C15 C16 119.68(17) . . ?
C6 C5 C4 117.35(19) . . ?
N1 C4 C5 130.13(18) . . ?
N1 C4 C3 107.37(16) . . ?
C5 C4 C3 122.50(18) . . ?
C5 C6 C7 121.2(2) . . ?
C18 C19 C20 118.59(18) . . ?
C18 C19 C21 121.05(19) . . ?
C20 C19 C21 120.36(19) . . ?
N1 C1 C2 110.34(17) . . ?
C8 C7 C6 121.6(2) . . ?
C15 C20 C19 120.94(18) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.041
