# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_d19102
_database_code_depnum_ccdc_archive 'CCDC 1589549'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O3 S'
_chemical_formula_sum            'C18 H22 N2 O3 S'
_chemical_formula_weight         346.44

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   'P 21/c'

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

_cell_length_a                   17.4170(10)
_cell_length_b                   7.3299(4)
_cell_length_c                   13.5997(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.370(2)
_cell_angle_gamma                90.00
_cell_volume                     1728.58(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8815
_cell_measurement_theta_min      3.018
_cell_measurement_theta_max      25.04

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9185
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24394
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.06
_reflns_number_total             3043
_reflns_number_gt                2569
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0269P)²+10.2763P] 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     SHELXL
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1895
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.249
_refine_ls_shift/su_mean         0.004

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
C1 C 0.6108(2) 0.3097(6) 0.3229(3) 0.0294(10) Uani 1 1 d . . .
C2 C 0.5433(3) 0.3936(7) 0.2821(3) 0.0348(11) Uani 1 1 d . . .
H2 H 0.5417 0.4525 0.2198 0.042 Uiso 1 1 calc R . .
C3 C 0.4788(3) 0.3895(7) 0.3339(4) 0.0364(11) Uani 1 1 d . . .
H3 H 0.4326 0.4457 0.3064 0.044 Uiso 1 1 calc R . .
C4 C 0.4802(3) 0.3049(7) 0.4256(4) 0.0372(12) Uani 1 1 d . . .
C5 C 0.4101(3) 0.3019(9) 0.4826(4) 0.0549(16) Uani 1 1 d . . .
H5A H 0.3711 0.3858 0.4519 0.082 Uiso 1 1 calc R . .
H5B H 0.4247 0.3399 0.5509 0.082 Uiso 1 1 calc R . .
H5C H 0.3889 0.1780 0.4822 0.082 Uiso 1 1 calc R . .
C6 C 0.5479(3) 0.2236(8) 0.4632(4) 0.0429(13) Uani 1 1 d . . .
H6 H 0.5495 0.1638 0.5253 0.051 Uiso 1 1 calc R . .
C7 C 0.6135(3) 0.2261(7) 0.4136(4) 0.0376(12) Uani 1 1 d . . .
H7 H 0.6598 0.1708 0.4417 0.045 Uiso 1 1 calc R . .
C8 C 0.6962(3) 0.6784(7) 0.2599(4) 0.0425(12) Uani 1 1 d . . .
H8A H 0.7308 0.7838 0.2680 0.064 Uiso 1 1 calc R . .
H8B H 0.6527 0.6961 0.2998 0.064 Uiso 1 1 calc R . .
H8C H 0.6768 0.6662 0.1902 0.064 Uiso 1 1 calc R . .
C9 C 0.7852(2) 0.5245(6) 0.3859(3) 0.0276(10) Uani 1 1 d . . .
C10 C 0.8533(2) 0.4112(6) 0.3984(3) 0.0305(10) Uani 1 1 d . . .
H10 H 0.8776 0.3738 0.3421 0.037 Uiso 1 1 calc R . .
C11 C 0.8828(3) 0.3582(6) 0.4886(4) 0.0321(11) Uani 1 1 d . . .
C12 C 0.9595(3) 0.2631(7) 0.5064(4) 0.0449(13) Uani 1 1 d . . .
H12A H 0.9790 0.2341 0.4428 0.067 Uiso 1 1 calc R . .
H12B H 0.9532 0.1502 0.5434 0.067 Uiso 1 1 calc R . .
H12C H 0.9963 0.3432 0.5444 0.067 Uiso 1 1 calc R . .
C13 C 0.8392(3) 0.4002(7) 0.5758(3) 0.0352(11) Uani 1 1 d . . .
H13A H 0.8613 0.3318 0.6345 0.042 Uiso 1 1 calc R . .
H13B H 0.7844 0.3652 0.5619 0.042 Uiso 1 1 calc R . .
C14 C 0.8460(3) 0.6031(7) 0.5943(3) 0.0322(11) Uani 1 1 d . . .
C15 C 0.8911(3) 0.6728(8) 0.6852(4) 0.0403(12) Uani 1 1 d . . .
C16 C 0.9147(4) 0.5452(11) 0.7667(5) 0.078(2) Uani 1 1 d . . .
H16A H 0.8714 0.4647 0.7779 0.117 Uiso 1 1 calc R . .
H16B H 0.9299 0.6145 0.8270 0.117 Uiso 1 1 calc R . .
H16C H 0.9584 0.4717 0.7491 0.117 Uiso 1 1 calc R . .
C17 C 0.8107(2) 0.7179(6) 0.5260(3) 0.0304(10) Uani 1 1 d . . .
C18 C 0.8081(3) 0.9214(7) 0.5309(4) 0.0494(14) Uani 1 1 d . . .
H18A H 0.8237 0.9727 0.4693 0.074 Uiso 1 1 calc R . .
H18B H 0.8435 0.9640 0.5865 0.074 Uiso 1 1 calc R . .
H18C H 0.7556 0.9610 0.5403 0.074 Uiso 1 1 calc R . .
N1 N 0.7386(2) 0.5116(6) 0.2927(3) 0.0323(9) Uani 1 1 d . . .
N2 N 0.7660(2) 0.6540(5) 0.4420(3) 0.0298(9) Uani 1 1 d . . .
O1 O 0.6710(2) 0.3350(6) 0.1561(2) 0.0497(11) Uani 1 1 d . . .
O2 O 0.74395(19) 0.1723(5) 0.2941(3) 0.0422(9) Uani 1 1 d . . .
O3 O 0.9097(3) 0.8320(7) 0.6944(4) 0.0864(17) Uani 1 1 d . . .
S1 S 0.69476(6) 0.31771(18) 0.25948(8) 0.0335(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 C7 1.374(6) . ?
C1 C2 1.395(6) . ?
C1 S1 1.766(4) . ?
C2 C3 1.381(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(7) . ?
C3 H3 0.9500 . ?
C4 C6 1.376(7) . ?
C4 C5 1.506(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.381(7) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.475(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.282(6) . ?
C9 N1 1.443(6) . ?
C9 C10 1.445(6) . ?
C10 C11 1.341(7) . ?
C10 H10 0.9500 . ?
C11 C13 1.500(7) . ?
C11 C12 1.506(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.511(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C17 1.357(7) . ?
C14 C15 1.491(7) . ?
C15 O3 1.215(7) . ?
C15 C16 1.479(8) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N2 1.402(6) . ?
C17 C18 1.494(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 S1 1.656(4) . ?
O1 S1 1.433(3) . ?
O2 S1 1.420(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
C7 C1 C2 120.6(4) . . ?
C7 C1 S1 119.5(4) . . ?
C2 C1 S1 119.8(3) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.4(5) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C6 C4 C3 118.0(4) . . ?
C6 C4 C5 120.6(5) . . ?
C3 C4 C5 121.4(5) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 122.1(5) . . ?
C7 C6 H6 118.9 . . ?
C4 C6 H6 118.9 . . ?
C1 C7 C6 119.0(5) . . ?
C1 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 N1 114.5(4) . . ?
N2 C9 C10 127.7(4) . . ?
N1 C9 C10 117.0(4) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C13 119.0(4) . . ?
C10 C11 C12 122.6(4) . . ?
C13 C11 C12 118.4(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 107.2(4) . . ?
C11 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
C11 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C17 C14 C15 121.6(5) . . ?
C17 C14 C13 118.2(4) . . ?
C15 C14 C13 120.2(4) . . ?
O3 C15 C16 118.5(5) . . ?
O3 C15 C14 122.0(5) . . ?
C16 C15 C14 119.5(5) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 N2 122.2(4) . . ?
C14 C17 C18 127.0(5) . . ?
N2 C17 C18 110.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 N1 C8 115.8(4) . . ?
C9 N1 S1 120.2(3) . . ?
C8 N1 S1 115.1(3) . . ?
C9 N2 C17 125.2(4) . . ?
O2 S1 O1 120.1(2) . . ?
O2 S1 N1 107.80(19) . . ?
O1 S1 N1 106.0(2) . . ?
O2 S1 C1 108.3(2) . . ?
O1 S1 C1 107.8(2) . . ?
N1 S1 C1 106.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_d19363
_database_code_depnum_ccdc_archive 'CCDC 1589559'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 N2 O3 S'
_chemical_formula_sum            'C28 H26 N2 O3 S'
_chemical_formula_weight         470.57

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   'P 21/c'

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

_cell_length_a                   13.9904(6)
_cell_length_b                   8.4064(3)
_cell_length_c                   21.3600(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.4910(10)
_cell_angle_gamma                90.00
_cell_volume                     2432.21(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.615
_cell_measurement_theta_max      25.004

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39822
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4281
_reflns_number_gt                3231
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0494P)²+0.9247P] 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         4281
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.15884(13) 0.7592(2) 0.52800(9) 0.0431(5) Uani 1 1 d . . .
C2 C 0.06212(14) 0.8075(3) 0.50573(10) 0.0509(5) Uani 1 1 d . . .
H2 H 0.0453 0.8882 0.4737 0.061 Uiso 1 1 calc R . .
C3 C -0.01035(15) 0.7374(3) 0.53035(11) 0.0532(6) Uani 1 1 d . . .
H3 H -0.0768 0.7716 0.5150 0.064 Uiso 1 1 calc R . .
C4 C 0.01127(15) 0.6197(2) 0.57639(10) 0.0481(5) Uani 1 1 d . . .
C5 C -0.06878(17) 0.5477(3) 0.60350(13) 0.0667(7) Uani 1 1 d . . .
H5A H -0.0578 0.5771 0.6491 0.100 Uiso 1 1 calc R . .
H5B H -0.0672 0.4316 0.5997 0.100 Uiso 1 1 calc R . .
H5C H -0.1333 0.5876 0.5793 0.100 Uiso 1 1 calc R . .
C6 C 0.10879(16) 0.5713(3) 0.59784(12) 0.0584(6) Uani 1 1 d . . .
H6 H 0.1253 0.4895 0.6294 0.070 Uiso 1 1 calc R . .
C7 C 0.18225(15) 0.6401(3) 0.57414(11) 0.0562(6) Uani 1 1 d . . .
H7 H 0.2487 0.6059 0.5895 0.067 Uiso 1 1 calc R . .
C8 C 0.26610(16) 1.0843(3) 0.57741(11) 0.0567(6) Uani 1 1 d . . .
H8A H 0.2190 1.0367 0.5990 0.085 Uiso 1 1 calc R . .
H8B H 0.2306 1.1510 0.5415 0.085 Uiso 1 1 calc R . .
H8C H 0.3136 1.1496 0.6084 0.085 Uiso 1 1 calc R . .
C9 C 0.40575(13) 0.8924(2) 0.59583(8) 0.0371(4) Uani 1 1 d . . .
C10 C 0.48561(13) 0.8526(2) 0.57200(9) 0.0397(4) Uani 1 1 d . . .
H10 H 0.4842 0.8719 0.5280 0.048 Uiso 1 1 calc R . .
C11 C 0.56750(13) 0.7847(2) 0.61286(9) 0.0377(4) Uani 1 1 d . . .
C12 C 0.65334(15) 0.7332(3) 0.58680(11) 0.0526(5) Uani 1 1 d . . .
H12A H 0.6391 0.7574 0.5405 0.079 Uiso 1 1 calc R . .
H12B H 0.6637 0.6185 0.5933 0.079 Uiso 1 1 calc R . .
H12C H 0.7130 0.7902 0.6096 0.079 Uiso 1 1 calc R . .
C13 C 0.56708(12) 0.7639(2) 0.67795(8) 0.0331(4) Uani 1 1 d . . .
C14 C 0.64882(12) 0.6707(2) 0.72180(9) 0.0376(4) Uani 1 1 d . . .
H14A H 0.6600 0.5730 0.6988 0.045 Uiso 1 1 calc R . .
H14B H 0.6262 0.6372 0.7602 0.045 Uiso 1 1 calc R . .
C15 C 0.74627(13) 0.7557(2) 0.74491(9) 0.0394(4) Uani 1 1 d . . .
C16 C 0.83591(13) 0.6570(2) 0.77123(9) 0.0388(4) Uani 1 1 d . . .
C17 C 0.92716(14) 0.7306(3) 0.78922(10) 0.0500(5) Uani 1 1 d . . .
H17 H 0.9317 0.8425 0.7842 0.060 Uiso 1 1 calc R . .
C18 C 1.01201(15) 0.6430(3) 0.81447(11) 0.0613(6) Uani 1 1 d . . .
H18 H 1.0744 0.6946 0.8264 0.074 Uiso 1 1 calc R . .
C19 C 1.00580(17) 0.4820(3) 0.82220(11) 0.0664(7) Uani 1 1 d . . .
H19 H 1.0637 0.4223 0.8404 0.080 Uiso 1 1 calc R . .
C20 C 0.91645(18) 0.4070(3) 0.80383(12) 0.0681(7) Uani 1 1 d . . .
H20 H 0.9128 0.2948 0.8083 0.082 Uiso 1 1 calc R . .
C21 C 0.83117(15) 0.4935(3) 0.77865(11) 0.0540(6) Uani 1 1 d . . .
H21 H 0.7693 0.4406 0.7664 0.065 Uiso 1 1 calc R . .
C22 C 0.48580(12) 0.8189(2) 0.69843(8) 0.0317(4) Uani 1 1 d . . .
C23 C 0.48136(12) 0.8142(2) 0.76765(8) 0.0325(4) Uani 1 1 d . . .
C24 C 0.55200(13) 0.8920(2) 0.81492(8) 0.0378(4) Uani 1 1 d . . .
H24 H 0.6066 0.9415 0.8039 0.045 Uiso 1 1 calc R . .
C25 C 0.54339(15) 0.8982(2) 0.87810(9) 0.0454(5) Uani 1 1 d . . .
H25 H 0.5912 0.9539 0.9100 0.055 Uiso 1 1 calc R . .
C26 C 0.46544(16) 0.8235(3) 0.89490(10) 0.0496(5) Uani 1 1 d . . .
H26 H 0.4593 0.8284 0.9382 0.059 Uiso 1 1 calc R . .
C27 C 0.39644(15) 0.7417(2) 0.84850(10) 0.0474(5) Uani 1 1 d . . .
H27 H 0.3439 0.6877 0.8602 0.057 Uiso 1 1 calc R . .
C28 C 0.40341(14) 0.7380(2) 0.78519(9) 0.0393(4) Uani 1 1 d . . .
H28 H 0.3549 0.6834 0.7534 0.047 Uiso 1 1 calc R . .
N1 N 0.31885(11) 0.9574(2) 0.55245(7) 0.0449(4) Uani 1 1 d . . .
N2 N 0.40424(10) 0.87962(17) 0.65759(7) 0.0343(3) Uani 1 1 d . . .
O1 O 0.20276(12) 0.9475(3) 0.44480(7) 0.0820(6) Uani 1 1 d . . .
O2 O 0.31328(11) 0.7179(2) 0.48402(8) 0.0713(5) Uani 1 1 d . . .
O3 O 0.75219(10) 0.90008(17) 0.74344(8) 0.0581(4) Uani 1 1 d . . .
S1 S 0.25114(4) 0.84385(8) 0.49596(2) 0.05433(19) 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 C2 1.378(3) . ?
C1 C7 1.385(3) . ?
C1 S1 1.756(2) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C6 1.387(3) . ?
C4 C5 1.510(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.470(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.329(2) . ?
C9 C10 1.380(3) . ?
C9 N1 1.440(2) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C13 1.403(2) . ?
C11 C12 1.508(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C22 1.395(2) . ?
C13 C14 1.504(2) . ?
C14 C15 1.509(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O3 1.217(2) . ?
C15 C16 1.492(2) . ?
C16 C17 1.384(3) . ?
C16 C21 1.387(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.367(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N2 1.351(2) . ?
C22 C23 1.496(2) . ?
C23 C24 1.388(2) . ?
C23 C28 1.394(2) . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.381(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.380(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N1 S1 1.6410(17) . ?
O1 S1 1.4288(17) . ?
O2 S1 1.4330(18) . ?

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
C2 C1 C7 119.7(2) . . ?
C2 C1 S1 120.01(16) . . ?
C7 C1 S1 120.27(15) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.80(19) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C6 118.0(2) . . ?
C3 C4 C5 120.77(19) . . ?
C6 C4 C5 121.2(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C4 C6 H6 119.4 . . ?
C6 C7 C1 119.89(19) . . ?
C6 C7 H7 120.1 . . ?
C1 C7 H7 120.1 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 124.20(16) . . ?
N2 C9 N1 116.67(15) . . ?
C10 C9 N1 119.08(16) . . ?
C11 C10 C9 119.23(17) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C13 118.04(16) . . ?
C10 C11 C12 119.85(17) . . ?
C13 C11 C12 122.11(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C22 C13 C11 118.38(16) . . ?
C22 C13 C14 121.98(16) . . ?
C11 C13 C14 119.39(15) . . ?
C13 C14 C15 116.16(15) . . ?
C13 C14 H14A 108.2 . . ?
C15 C14 H14A 108.2 . . ?
C13 C14 H14B 108.2 . . ?
C15 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
O3 C15 C16 120.55(17) . . ?
O3 C15 C14 121.72(17) . . ?
C16 C15 C14 117.72(16) . . ?
C17 C16 C21 118.61(18) . . ?
C17 C16 C15 119.06(18) . . ?
C21 C16 C15 122.33(17) . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
N2 C22 C13 123.06(15) . . ?
N2 C22 C23 114.27(14) . . ?
C13 C22 C23 122.67(15) . . ?
C24 C23 C28 118.92(16) . . ?
C24 C23 C22 120.57(15) . . ?
C28 C23 C22 120.43(16) . . ?
C25 C24 C23 120.44(17) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.18(19) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.69(18) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 120.41(18) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C23 120.31(18) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C9 N1 C8 117.51(15) . . ?
C9 N1 S1 119.42(14) . . ?
C8 N1 S1 116.02(13) . . ?
C9 N2 C22 116.79(15) . . ?
O1 S1 O2 120.46(11) . . ?
O1 S1 N1 106.46(11) . . ?
O2 S1 N1 107.26(9) . . ?
O1 S1 C1 106.94(10) . . ?
O2 S1 C1 107.92(11) . . ?
N1 S1 C1 107.15(9) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_d19315
_database_code_depnum_ccdc_archive 'CCDC 1589558'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O3 S'
_chemical_formula_sum            'C18 H22 N2 O3 S'
_chemical_formula_weight         346.44

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   'P 21/c'

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

_cell_length_a                   12.3308(12)
_cell_length_b                   16.1714(13)
_cell_length_c                   8.8646(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.241(4)
_cell_angle_gamma                90.00
_cell_volume                     1762.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3678
_cell_measurement_theta_min      2.628
_cell_measurement_theta_max      24.61

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8885
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14290
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_sigmaI/netI    0.0842
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3096
_reflns_number_gt                1955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0527P)²+1.4791P] 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         3096
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1630
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.1885(3) 0.4274(2) 0.6765(4) 0.0380(8) Uani 1 1 d . . .
C2 C 0.0816(3) 0.4008(3) 0.6610(5) 0.0613(12) Uani 1 1 d . . .
H2 H 0.0464 0.3923 0.5633 0.074 Uiso 1 1 calc R . .
C3 C 0.0269(3) 0.3866(3) 0.7879(5) 0.0659(13) Uani 1 1 d . . .
H3 H -0.0463 0.3679 0.7759 0.079 Uiso 1 1 calc R . .
C4 C 0.0740(3) 0.3985(2) 0.9314(5) 0.0472(10) Uani 1 1 d . . .
C5 C 0.0146(4) 0.3819(3) 1.0706(5) 0.0646(12) Uani 1 1 d . . .
H5A H -0.0634 0.3912 1.0478 0.097 Uiso 1 1 calc R . .
H5B H 0.0418 0.4192 1.1520 0.097 Uiso 1 1 calc R . .
H5C H 0.0268 0.3244 1.1026 0.097 Uiso 1 1 calc R . .
C6 C 0.1813(3) 0.4262(2) 0.9454(5) 0.0481(10) Uani 1 1 d . . .
H6 H 0.2160 0.4354 1.0433 0.058 Uiso 1 1 calc R . .
C7 C 0.2378(3) 0.4406(2) 0.8197(4) 0.0445(9) Uani 1 1 d . . .
H7 H 0.3108 0.4595 0.8314 0.053 Uiso 1 1 calc R . .
C8 C 0.2453(3) 0.2912(2) 0.3996(5) 0.0527(11) Uani 1 1 d . . .
H8A H 0.2003 0.3186 0.3187 0.079 Uiso 1 1 calc R . .
H8B H 0.1984 0.2662 0.4716 0.079 Uiso 1 1 calc R . .
H8C H 0.2894 0.2481 0.3561 0.079 Uiso 1 1 calc R . .
C9 C 0.4053(3) 0.3202(2) 0.5781(4) 0.0341(8) Uani 1 1 d . . .
C10 C 0.4864(3) 0.3697(2) 0.6487(4) 0.0361(8) Uani 1 1 d . . .
H10 H 0.4864 0.4278 0.6327 0.043 Uiso 1 1 calc R . .
C11 C 0.5671(3) 0.3327(2) 0.7427(4) 0.0353(8) Uani 1 1 d . . .
C12 C 0.6562(3) 0.3858(2) 0.8180(4) 0.0483(10) Uani 1 1 d . . .
H12A H 0.7254 0.3725 0.7761 0.072 Uiso 1 1 calc R . .
H12B H 0.6620 0.3751 0.9271 0.072 Uiso 1 1 calc R . .
H12C H 0.6389 0.4442 0.7997 0.072 Uiso 1 1 calc R . .
C13 C 0.5663(3) 0.2466(2) 0.7599(4) 0.0338(8) Uani 1 1 d . . .
C14 C 0.4857(3) 0.2017(2) 0.6770(4) 0.0363(8) Uani 1 1 d . . .
C15 C 0.4817(3) 0.1088(2) 0.6783(5) 0.0488(10) Uani 1 1 d . . .
H15A H 0.4329 0.0894 0.5934 0.073 Uiso 1 1 calc R . .
H15B H 0.4548 0.0898 0.7736 0.073 Uiso 1 1 calc R . .
H15C H 0.5548 0.0867 0.6686 0.073 Uiso 1 1 calc R . .
C16 C 0.6521(3) 0.2042(2) 0.8640(4) 0.0380(8) Uani 1 1 d . A .
H16A H 0.6641 0.2378 0.9572 0.046 Uiso 1 1 calc R . .
H16B H 0.6233 0.1499 0.8937 0.046 Uiso 1 1 calc R . .
C17 C 0.7599(3) 0.1905(2) 0.7999(4) 0.0445(9) Uani 1 1 d . . .
C18 C 0.8508(3) 0.1630(3) 0.9069(4) 0.0532(11) Uani 1 1 d . A .
H18A H 0.9064 0.1358 0.8507 0.080 Uiso 1 1 calc R . .
H18B H 0.8235 0.1239 0.9797 0.080 Uiso 1 1 calc R . .
H18C H 0.8828 0.2109 0.9611 0.080 Uiso 1 1 calc R . .
N1 N 0.3178(2) 0.35282(16) 0.4790(3) 0.0387(7) Uani 1 1 d . . .
N2 N 0.4050(2) 0.23843(16) 0.5904(3) 0.0362(7) Uani 1 1 d . . .
O1 O 0.34383(19) 0.50184(14) 0.5500(3) 0.0474(7) Uani 1 1 d . . .
O2 O 0.1829(2) 0.45732(15) 0.3883(3) 0.0531(7) Uani 1 1 d . . .
O3 O 0.7826(4) 0.2193(4) 0.6752(6) 0.0458(14) Uiso 0.50 1 d P A 1
O3' O 0.7613(4) 0.1832(3) 0.6601(6) 0.0417(13) Uiso 0.50 1 d P A 2
S1 S 0.25969(7) 0.44219(5) 0.51379(11) 0.0413(3) 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 C7 1.383(5) . ?
C1 C2 1.384(5) . ?
C1 S1 1.759(4) . ?
C2 C3 1.373(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(5) . ?
C3 H3 0.9500 . ?
C4 C6 1.394(5) . ?
C4 C5 1.505(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.377(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.480(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.327(4) . ?
C9 C10 1.392(4) . ?
C9 N1 1.441(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C13 1.400(5) . ?
C11 C12 1.510(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.395(4) . ?
C13 C16 1.515(4) . ?
C14 N2 1.349(4) . ?
C14 C15 1.503(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.500(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O3' 1.246(6) . ?
C17 O3 1.250(6) . ?
C17 C18 1.483(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 S1 1.652(3) . ?
O1 S1 1.435(2) . ?
O2 S1 1.427(2) . ?

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
C7 C1 C2 119.3(4) . . ?
C7 C1 S1 121.3(3) . . ?
C2 C1 S1 119.4(3) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 122.4(4) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C6 117.5(4) . . ?
C3 C4 C5 122.5(4) . . ?
C6 C4 C5 120.0(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C4 C6 H6 119.5 . . ?
C6 C7 C1 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C1 C7 H7 119.9 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 122.8(3) . . ?
N2 C9 N1 114.1(3) . . ?
C10 C9 N1 123.0(3) . . ?
C11 C10 C9 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C13 119.0(3) . . ?
C10 C11 C12 119.1(3) . . ?
C13 C11 C12 121.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 118.0(3) . . ?
C14 C13 C16 121.6(3) . . ?
C11 C13 C16 120.4(3) . . ?
N2 C14 C13 122.5(3) . . ?
N2 C14 C15 114.9(3) . . ?
C13 C14 C15 122.6(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 115.7(3) . . ?
C17 C16 H16A 108.3 . . ?
C13 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
C13 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
O3' C17 O3 30.2(3) . . ?
O3' C17 C18 122.8(4) . . ?
O3 C17 C18 118.0(4) . . ?
O3' C17 C16 117.9(4) . . ?
O3 C17 C16 122.9(4) . . ?
C18 C17 C16 116.8(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 N1 C8 116.3(3) . . ?
C9 N1 S1 121.4(2) . . ?
C8 N1 S1 115.0(2) . . ?
C9 N2 C14 118.6(3) . . ?
O2 S1 O1 119.06(15) . . ?
O2 S1 N1 106.02(15) . . ?
O1 S1 N1 108.27(15) . . ?
O2 S1 C1 108.63(17) . . ?
O1 S1 C1 107.72(16) . . ?
N1 S1 C1 106.50(16) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_d19354
_database_code_depnum_ccdc_archive 'CCDC 1589560'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N2 O3 S'
_chemical_formula_sum            'C21 H26 N2 O3 S'
_chemical_formula_weight         386.50

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   'P 21/n'

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

_cell_length_a                   9.0836(3)
_cell_length_b                   21.4854(9)
_cell_length_c                   9.9912(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.1120(10)
_cell_angle_gamma                90.00
_cell_volume                     1948.61(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4617
_cell_measurement_theta_min      2.251
_cell_measurement_theta_max      24.955

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17674
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3430
_reflns_number_gt                2654
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0517P)²+2.1642P] 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         3430
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2597(3) 0.63487(12) 0.5365(3) 0.0286(6) Uani 1 1 d . . .
C2 C 0.2560(3) 0.68981(13) 0.4648(3) 0.0374(7) Uani 1 1 d . . .
H2 H 0.3340 0.7190 0.4756 0.045 Uiso 1 1 calc R . .
C3 C 0.1381(3) 0.70207(14) 0.3773(3) 0.0370(7) Uani 1 1 d . . .
H3 H 0.1357 0.7400 0.3284 0.044 Uiso 1 1 calc R . .
C4 C 0.0233(3) 0.65996(13) 0.3597(3) 0.0328(6) Uani 1 1 d . . .
C5 C -0.1002(3) 0.67271(16) 0.2591(3) 0.0437(8) Uani 1 1 d . . .
H5A H -0.0838 0.7130 0.2160 0.066 Uiso 1 1 calc R . .
H5B H -0.1939 0.6737 0.3046 0.066 Uiso 1 1 calc R . .
H5C H -0.1033 0.6398 0.1911 0.066 Uiso 1 1 calc R . .
C6 C 0.0278(3) 0.60586(14) 0.4349(3) 0.0357(7) Uani 1 1 d . . .
H6 H -0.0514 0.5771 0.4259 0.043 Uiso 1 1 calc R . .
C7 C 0.1449(3) 0.59254(13) 0.5229(3) 0.0329(6) Uani 1 1 d . . .
H7 H 0.1466 0.5550 0.5731 0.039 Uiso 1 1 calc R . .
C8 C 0.5672(3) 0.58071(14) 0.4469(3) 0.0402(7) Uani 1 1 d . . .
H8A H 0.4697 0.5642 0.4207 0.060 Uiso 1 1 calc R . .
H8B H 0.6318 0.5465 0.4765 0.060 Uiso 1 1 calc R . .
H8C H 0.6094 0.6016 0.3701 0.060 Uiso 1 1 calc R . .
C9 C 0.6817(3) 0.65471(11) 0.6101(2) 0.0244(6) Uani 1 1 d . . .
C10 C 0.7783(3) 0.63779(11) 0.7114(2) 0.0236(5) Uani 1 1 d . . .
C11 C 0.7644(3) 0.58136(12) 0.7962(3) 0.0261(6) Uani 1 1 d . . .
C12 C 0.7944(3) 0.52464(12) 0.7481(3) 0.0324(6) Uani 1 1 d . . .
H12 H 0.8280 0.5217 0.6594 0.039 Uiso 1 1 calc R . .
C13 C 0.7778(3) 0.46556(13) 0.8264(3) 0.0398(7) Uani 1 1 d . . .
H13A H 0.8763 0.4503 0.8567 0.048 Uiso 1 1 calc R . .
H13B H 0.7312 0.4333 0.7680 0.048 Uiso 1 1 calc R . .
C14 C 0.6844(3) 0.47617(14) 0.9470(3) 0.0408(7) Uani 1 1 d . . .
H14A H 0.5799 0.4811 0.9170 0.049 Uiso 1 1 calc R . .
H14B H 0.6918 0.4396 1.0070 0.049 Uiso 1 1 calc R . .
C15 C 0.7349(3) 0.53372(14) 1.0226(3) 0.0398(7) Uani 1 1 d . . .
H15A H 0.8403 0.5295 1.0501 0.048 Uiso 1 1 calc R . .
H15B H 0.6778 0.5383 1.1045 0.048 Uiso 1 1 calc R . .
C16 C 0.7137(3) 0.59090(13) 0.9352(3) 0.0350(7) Uani 1 1 d . . .
H16A H 0.6079 0.6022 0.9309 0.042 Uiso 1 1 calc R . .
H16B H 0.7688 0.6261 0.9767 0.042 Uiso 1 1 calc R . .
C17 C 0.8834(3) 0.68772(11) 0.7242(2) 0.0234(5) Uani 1 1 d . . .
C18 C 1.0106(3) 0.69362(12) 0.8155(3) 0.0267(6) Uani 1 1 d . . .
C19 C 1.0733(3) 0.63777(13) 0.8864(3) 0.0369(7) Uani 1 1 d . . .
H19A H 1.1580 0.6503 0.9437 0.055 Uiso 1 1 calc R . .
H19B H 1.1050 0.6073 0.8204 0.055 Uiso 1 1 calc R . .
H19C H 0.9980 0.6191 0.9415 0.055 Uiso 1 1 calc R . .
C20 C 0.8447(3) 0.73252(12) 0.6274(3) 0.0250(6) Uani 1 1 d . . .
C21 C 0.9161(3) 0.79227(13) 0.5917(3) 0.0341(6) Uani 1 1 d . . .
H21A H 0.8592 0.8122 0.5183 0.051 Uiso 1 1 calc R . .
H21B H 1.0165 0.7841 0.5635 0.051 Uiso 1 1 calc R . .
H21C H 0.9197 0.8199 0.6699 0.051 Uiso 1 1 calc R . .
N1 N 0.5531(2) 0.62520(10) 0.5563(2) 0.0281(5) Uani 1 1 d . . .
N2 N 0.7230(2) 0.71189(10) 0.5600(2) 0.0254(5) Uani 1 1 d . . .
O1 O 0.4223(2) 0.66708(10) 0.74771(19) 0.0412(5) Uani 1 1 d . . .
O2 O 0.3909(2) 0.55574(9) 0.6944(2) 0.0417(5) Uani 1 1 d . . .
O3 O 1.0708(2) 0.74456(9) 0.83470(19) 0.0362(5) Uani 1 1 d . . .
S1 S 0.40923(7) 0.61865(3) 0.64975(7) 0.0301(2) Uani 1 1 d . . .
H2' H 0.6792 0.7298 0.4840 0.036 Uiso 1 1 d 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
C1 C2 1.381(4) . ?
C1 C7 1.387(4) . ?
C1 S1 1.770(3) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C6 1.383(4) . ?
C4 C5 1.504(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.461(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.365(3) . ?
C9 N2 1.384(3) . ?
C9 N1 1.418(3) . ?
C10 C17 1.438(3) . ?
C10 C11 1.487(3) . ?
C11 C12 1.342(4) . ?
C11 C16 1.493(4) . ?
C12 C13 1.501(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.516(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.512(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.516(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.400(3) . ?
C17 C18 1.451(3) . ?
C18 O3 1.235(3) . ?
C18 C19 1.495(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N2 1.348(3) . ?
C20 C21 1.488(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 S1 1.640(2) . ?
N2 H2' 0.9278 . ?
O1 S1 1.430(2) . ?
O2 S1 1.435(2) . ?

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
C2 C1 C7 120.4(3) . . ?
C2 C1 S1 120.2(2) . . ?
C7 C1 S1 119.4(2) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C6 C4 C3 118.2(3) . . ?
C6 C4 C5 121.5(3) . . ?
C3 C4 C5 120.3(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 121.7(3) . . ?
C4 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C1 118.9(3) . . ?
C6 C7 H7 120.5 . . ?
C1 C7 H7 120.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N2 109.2(2) . . ?
C10 C9 N1 131.4(2) . . ?
N2 C9 N1 119.4(2) . . ?
C9 C10 C17 105.9(2) . . ?
C9 C10 C11 125.0(2) . . ?
C17 C10 C11 128.9(2) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 C16 122.1(2) . . ?
C10 C11 C16 117.0(2) . . ?
C11 C12 C13 123.8(3) . . ?
C11 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C12 C13 C14 110.9(2) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C13 110.6(2) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 110.2(2) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 C15 112.8(2) . . ?
C11 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C11 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C20 C17 C10 107.6(2) . . ?
C20 C17 C18 123.2(2) . . ?
C10 C17 C18 129.1(2) . . ?
O3 C18 C17 120.8(2) . . ?
O3 C18 C19 118.6(2) . . ?
C17 C18 C19 120.5(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C17 107.4(2) . . ?
N2 C20 C21 121.4(2) . . ?
C17 C20 C21 131.2(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 N1 C8 118.8(2) . . ?
C9 N1 S1 119.05(17) . . ?
C8 N1 S1 117.61(18) . . ?
C20 N2 C9 109.9(2) . . ?
C20 N2 H2' 126.3 . . ?
C9 N2 H2' 123.4 . . ?
O1 S1 O2 118.67(13) . . ?
O1 S1 N1 106.22(11) . . ?
O2 S1 N1 111.22(12) . . ?
O1 S1 C1 109.66(12) . . ?
O2 S1 C1 106.81(12) . . ?
N1 S1 C1 103.19(12) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_d19423
_database_code_depnum_ccdc_archive 'CCDC 1589562'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N2 O3 S'
_chemical_formula_sum            'C24 H26 N2 O3 S'
_chemical_formula_weight         422.53

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   'P 21/c'

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

_cell_length_a                   9.8261(4)
_cell_length_b                   13.6201(5)
_cell_length_c                   16.2063(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.8680(10)
_cell_angle_gamma                90.00
_cell_volume                     2153.37(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      2.568
_cell_measurement_theta_max      25.022

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9066
_exptl_absorpt_correction_T_max  0.9772
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31582
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3775
_reflns_number_gt                3246
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0369P)²+1.6109P] 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         3775
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.047
_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
C1 C 0.34159(17) 0.77050(12) 0.68211(10) 0.0292(4) Uani 1 1 d . . .
C2 C 0.43401(19) 0.70252(14) 0.71901(12) 0.0379(4) Uani 1 1 d . . .
H2 H 0.5250 0.7006 0.7047 0.045 Uiso 1 1 calc R . .
C3 C 0.3936(2) 0.63757(14) 0.77662(12) 0.0390(4) Uani 1 1 d . . .
H3 H 0.4577 0.5913 0.8021 0.047 Uiso 1 1 calc R . .
C4 C 0.26097(19) 0.63850(14) 0.79810(11) 0.0335(4) Uani 1 1 d . . .
C5 C 0.2162(2) 0.56543(16) 0.85899(13) 0.0468(5) Uani 1 1 d . . .
H5A H 0.1159 0.5612 0.8521 0.070 Uiso 1 1 calc R . .
H5B H 0.2487 0.5866 0.9157 0.070 Uiso 1 1 calc R . .
H5C H 0.2549 0.5009 0.8488 0.070 Uiso 1 1 calc R . .
C6 C 0.1706(2) 0.70735(16) 0.76042(12) 0.0442(5) Uani 1 1 d . . .
H6 H 0.0797 0.7095 0.7747 0.053 Uiso 1 1 calc R . .
C7 C 0.20911(19) 0.77306(15) 0.70251(12) 0.0407(5) Uani 1 1 d . . .
H7 H 0.1452 0.8195 0.6770 0.049 Uiso 1 1 calc R . .
C8 C 0.29776(18) 0.72070(15) 0.49723(12) 0.0383(4) Uani 1 1 d . . .
H8A H 0.2975 0.7081 0.4377 0.057 Uiso 1 1 calc R . .
H8B H 0.2128 0.7544 0.5066 0.057 Uiso 1 1 calc R . .
H8C H 0.3041 0.6583 0.5275 0.057 Uiso 1 1 calc R . .
C9 C 0.54745(17) 0.75361(13) 0.50721(10) 0.0275(4) Uani 1 1 d . . .
C10 C 0.65297(17) 0.82782(13) 0.50559(10) 0.0284(4) Uani 1 1 d . . .
H10 H 0.6262 0.8942 0.4956 0.034 Uiso 1 1 calc R . .
C11 C 0.78683(17) 0.80610(12) 0.51770(10) 0.0269(4) Uani 1 1 d . . .
C12 C 0.89607(18) 0.88029(14) 0.50733(12) 0.0351(4) Uani 1 1 d . . .
H12A H 0.9516 0.8576 0.4647 0.053 Uiso 1 1 calc R . .
H12B H 0.9547 0.8885 0.5602 0.053 Uiso 1 1 calc R . .
H12C H 0.8533 0.9433 0.4903 0.053 Uiso 1 1 calc R . .
C13 C 0.83511(17) 0.70325(12) 0.54180(10) 0.0274(4) Uani 1 1 d . . .
H13 H 0.9375 0.7055 0.5477 0.033 Uiso 1 1 calc R . .
C14 C 0.79682(16) 0.66742(13) 0.62531(10) 0.0277(4) Uani 1 1 d . . .
C15 C 0.80598(18) 0.73179(14) 0.69229(11) 0.0346(4) Uani 1 1 d . . .
H15 H 0.8246 0.7993 0.6839 0.042 Uiso 1 1 calc R . .
C16 C 0.7883(2) 0.69869(16) 0.77121(11) 0.0418(5) Uani 1 1 d . . .
H16 H 0.7956 0.7435 0.8165 0.050 Uiso 1 1 calc R . .
C17 C 0.76033(19) 0.60139(17) 0.78438(12) 0.0430(5) Uani 1 1 d . . .
H17 H 0.7494 0.5786 0.8386 0.052 Uiso 1 1 calc R . .
C18 C 0.7483(2) 0.53750(16) 0.71837(12) 0.0450(5) Uani 1 1 d . . .
H18 H 0.7271 0.4705 0.7269 0.054 Uiso 1 1 calc R . .
C19 C 0.7668(2) 0.57007(14) 0.63916(12) 0.0382(4) Uani 1 1 d . . .
H19 H 0.7588 0.5250 0.5941 0.046 Uiso 1 1 calc R . .
C20 C 0.79164(18) 0.63733(12) 0.46761(10) 0.0286(4) Uani 1 1 d . . .
C21 C 0.9071(2) 0.59602(14) 0.42700(12) 0.0379(4) Uani 1 1 d . . .
C22 C 0.8887(3) 0.5201(3) 0.3610(2) 0.1034(14) Uani 1 1 d . . .
H22A H 0.8493 0.5503 0.3087 0.155 Uiso 1 1 calc R . .
H22B H 0.8268 0.4688 0.3769 0.155 Uiso 1 1 calc R . .
H22C H 0.9778 0.4910 0.3539 0.155 Uiso 1 1 calc R . .
C23 C 0.65648(19) 0.62396(13) 0.44172(11) 0.0337(4) Uani 1 1 d . . .
C24 C 0.5931(2) 0.5623(2) 0.36964(17) 0.0741(9) Uani 1 1 d . . .
H24A H 0.6324 0.5812 0.3191 0.111 Uiso 1 1 calc R . .
H24B H 0.4938 0.5730 0.3615 0.111 Uiso 1 1 calc R . .
H24C H 0.6121 0.4928 0.3816 0.111 Uiso 1 1 calc R . .
N1 N 0.41659(14) 0.78308(11) 0.52723(9) 0.0307(3) Uani 1 1 d . . .
N2 N 0.55149(15) 0.66442(11) 0.48129(9) 0.0317(3) Uani 1 1 d . . .
O1 O 0.52246(14) 0.89519(10) 0.63858(8) 0.0415(3) Uani 1 1 d . . .
O2 O 0.27923(14) 0.91563(10) 0.58273(9) 0.0453(4) Uani 1 1 d . . .
O3 O 1.02204(17) 0.62313(16) 0.44849(14) 0.0899(7) Uani 1 1 d . . .
S1 S 0.39336(5) 0.85276(3) 0.60797(3) 0.03225(14) 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 C7 1.381(3) . ?
C1 C2 1.382(2) . ?
C1 S1 1.7617(18) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C6 1.382(3) . ?
C4 C5 1.504(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.478(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.288(2) . ?
C9 N1 1.421(2) . ?
C9 C10 1.451(2) . ?
C10 C11 1.340(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.498(2) . ?
C11 C13 1.515(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C20 1.520(2) . ?
C13 C14 1.527(2) . ?
C13 H13 1.0000 . ?
C14 C19 1.382(3) . ?
C14 C15 1.390(2) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C23 1.356(2) . ?
C20 C21 1.489(2) . ?
C21 O3 1.199(2) . ?
C21 C22 1.483(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N2 1.392(2) . ?
C23 C24 1.511(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 S1 1.6542(15) . ?
O1 S1 1.4278(14) . ?
O2 S1 1.4313(14) . ?

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
C7 C1 C2 120.18(17) . . ?
C7 C1 S1 120.29(14) . . ?
C2 C1 S1 119.52(13) . . ?
C3 C2 C1 119.70(17) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.25(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C6 C4 C3 117.91(17) . . ?
C6 C4 C5 121.07(17) . . ?
C3 C4 C5 121.01(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.72(18) . . ?
C7 C6 H6 119.1 . . ?
C4 C6 H6 119.1 . . ?
C1 C7 C6 119.24(17) . . ?
C1 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 N1 113.89(15) . . ?
N2 C9 C10 126.98(16) . . ?
N1 C9 C10 118.40(15) . . ?
C11 C10 C9 122.34(16) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 122.60(16) . . ?
C10 C11 C13 120.90(15) . . ?
C12 C11 C13 116.49(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C20 107.01(13) . . ?
C11 C13 C14 114.90(14) . . ?
C20 C13 C14 115.87(14) . . ?
C11 C13 H13 106.1 . . ?
C20 C13 H13 106.1 . . ?
C14 C13 H13 106.1 . . ?
C19 C14 C15 118.25(16) . . ?
C19 C14 C13 122.02(16) . . ?
C15 C14 C13 119.39(15) . . ?
C16 C15 C14 120.79(18) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 120.39(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.34(18) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.56(19) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 120.66(18) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C23 C20 C21 125.62(16) . . ?
C23 C20 C13 119.74(15) . . ?
C21 C20 C13 114.57(15) . . ?
O3 C21 C22 116.98(19) . . ?
O3 C21 C20 119.75(17) . . ?
C22 C21 C20 123.27(18) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 N2 123.82(16) . . ?
C20 C23 C24 127.69(17) . . ?
N2 C23 C24 108.46(16) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C8 117.59(14) . . ?
C9 N1 S1 123.84(11) . . ?
C8 N1 S1 114.31(12) . . ?
C9 N2 C23 125.26(15) . . ?
O1 S1 O2 119.36(9) . . ?
O1 S1 N1 107.83(8) . . ?
O2 S1 N1 107.13(8) . . ?
O1 S1 C1 109.72(8) . . ?
O2 S1 C1 107.17(8) . . ?
N1 S1 C1 104.65(8) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_ch19381
_database_code_depnum_ccdc_archive 'CCDC 1589561'
_audit_update_record             
;
2017-12-06 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O3 S'
_chemical_formula_sum            'C16 H18 N2 O3 S'
_chemical_formula_weight         318.38

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                   10.9900(11)
_cell_length_b                   9.6096(9)
_cell_length_c                   29.660(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.047(7)
_cell_angle_gamma                90.00
_cell_volume                     3124.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1255
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      21.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8336
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2790
_reflns_number_gt                1656
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0682P)²+3.3752P] 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         2790
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
C1 C 0.5071(3) 0.4504(4) 0.57284(12) 0.0311(9) Uani 1 1 d . . .
C2 C 0.5405(3) 0.5786(4) 0.55663(13) 0.0356(10) Uani 1 1 d . . .
H2 H 0.4880 0.6565 0.5586 0.043 Uiso 1 1 calc R . .
C3 C 0.6510(4) 0.5926(4) 0.53742(13) 0.0389(10) Uani 1 1 d . . .
H3 H 0.6743 0.6805 0.5261 0.047 Uiso 1 1 calc R . .
C4 C 0.7279(3) 0.4792(5) 0.53455(13) 0.0400(10) Uani 1 1 d . . .
C5 C 0.8525(3) 0.4973(5) 0.51582(15) 0.0545(12) Uani 1 1 d . . .
H5A H 0.8630 0.5946 0.5069 0.082 Uiso 1 1 calc R . .
H5B H 0.8582 0.4370 0.4894 0.082 Uiso 1 1 calc R . .
H5C H 0.9165 0.4721 0.5391 0.082 Uiso 1 1 calc R . .
C6 C 0.6922(3) 0.3509(4) 0.54967(13) 0.0406(10) Uani 1 1 d . . .
H6 H 0.7437 0.2724 0.5468 0.049 Uiso 1 1 calc R . .
C7 C 0.5821(3) 0.3352(4) 0.56900(13) 0.0370(10) Uani 1 1 d . . .
H7 H 0.5580 0.2466 0.5795 0.044 Uiso 1 1 calc R . .
C8 C 0.4779(4) 0.3409(4) 0.67860(15) 0.0551(13) Uani 1 1 d . . .
H8A H 0.4378 0.2555 0.6672 0.083 Uiso 1 1 calc R . .
H8B H 0.4704 0.3482 0.7112 0.083 Uiso 1 1 calc R . .
H8C H 0.5644 0.3382 0.6725 0.083 Uiso 1 1 calc R . .
C9 C 0.4660(3) 0.5961(4) 0.66864(13) 0.0307(9) Uani 1 1 d . . .
C10 C 0.3873(3) 0.7159(4) 0.65936(12) 0.0307(9) Uani 1 1 d . . .
H10 H 0.3016 0.7020 0.6582 0.037 Uiso 1 1 calc R . .
C11 C 0.4284(3) 0.8439(4) 0.65244(12) 0.0325(9) Uani 1 1 d . . .
C12 C 0.3467(4) 0.9692(4) 0.64971(14) 0.0460(11) Uani 1 1 d . . .
H12A H 0.3954 1.0527 0.6450 0.069 Uiso 1 1 calc R . .
H12B H 0.3061 0.9784 0.6779 0.069 Uiso 1 1 calc R . .
H12C H 0.2852 0.9582 0.6244 0.069 Uiso 1 1 calc R . .
C13 C 0.5630(3) 0.8682(4) 0.64904(13) 0.0367(10) Uani 1 1 d . . .
H13A H 0.5956 0.8044 0.6266 0.044 Uiso 1 1 calc R . .
H13B H 0.5784 0.9653 0.6398 0.044 Uiso 1 1 calc R . .
C14 C 0.6215(3) 0.8404(4) 0.69524(13) 0.0358(10) Uani 1 1 d . . .
C15 C 0.6735(3) 0.9536(5) 0.72320(15) 0.0455(11) Uani 1 1 d . . .
H15 H 0.7213 0.9176 0.7527 0.055 Uiso 1 1 d R . .
C16 C 0.6191(3) 0.7132(4) 0.71322(14) 0.0380(10) Uani 1 1 d . . .
H16 H 0.6573 0.7033 0.7428 0.046 Uiso 1 1 calc R . .
N1 N 0.4197(3) 0.4619(3) 0.65584(10) 0.0350(8) Uani 1 1 d . . .
N2 N 0.5677(3) 0.5941(3) 0.69391(11) 0.0366(8) Uani 1 1 d . . .
O1 O 0.2931(2) 0.5463(3) 0.58758(9) 0.0423(7) Uani 1 1 d . . .
O2 O 0.3316(2) 0.2949(3) 0.59868(10) 0.0465(8) Uani 1 1 d . . .
O3 O 0.6628(3) 1.0767(3) 0.71353(10) 0.0560(9) Uani 1 1 d . . .
S1 S 0.37357(8) 0.43567(10) 0.60175(3) 0.0349(3) 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 C2 1.381(5) . ?
C1 C7 1.390(5) . ?
C1 S1 1.757(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(6) . ?
C3 H3 0.9500 . ?
C4 C6 1.379(5) . ?
C4 C5 1.524(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.468(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N2 1.301(4) . ?
C9 N1 1.428(5) . ?
C9 C10 1.454(5) . ?
C10 C11 1.331(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.501(5) . ?
C11 C13 1.507(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.496(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.335(5) . ?
C14 C15 1.460(5) . ?
C15 O3 1.221(5) . ?
C15 H15 1.0482 . ?
C16 N2 1.383(5) . ?
C16 H16 0.9500 . ?
N1 S1 1.667(3) . ?
O1 S1 1.427(3) . ?
O2 S1 1.430(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
C2 C1 C7 120.6(4) . . ?
C2 C1 S1 119.6(3) . . ?
C7 C1 S1 119.7(3) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C6 C4 C3 119.7(4) . . ?
C6 C4 C5 120.3(4) . . ?
C3 C4 C5 120.0(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 120.6(4) . . ?
C4 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C1 119.2(4) . . ?
C6 C7 H7 120.4 . . ?
C1 C7 H7 120.4 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 N1 114.5(3) . . ?
N2 C9 C10 126.6(3) . . ?
N1 C9 C10 118.0(3) . . ?
C11 C10 C9 123.8(3) . . ?
C11 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C10 C11 C12 122.7(3) . . ?
C10 C11 C13 119.9(3) . . ?
C12 C11 C13 117.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 105.8(3) . . ?
C14 C13 H13A 110.6 . . ?
C11 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C11 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C16 C14 C15 118.3(4) . . ?
C16 C14 C13 120.7(4) . . ?
C15 C14 C13 120.8(4) . . ?
O3 C15 C14 124.1(4) . . ?
O3 C15 H15 123.4 . . ?
C14 C15 H15 112.5 . . ?
C14 C16 N2 127.7(4) . . ?
C14 C16 H16 116.2 . . ?
N2 C16 H16 116.2 . . ?
C9 N1 C8 117.2(3) . . ?
C9 N1 S1 118.1(2) . . ?
C8 N1 S1 114.6(3) . . ?
C9 N2 C16 122.4(3) . . ?
O1 S1 O2 119.70(16) . . ?
O1 S1 N1 108.12(16) . . ?
O2 S1 N1 106.19(17) . . ?
O1 S1 C1 108.52(18) . . ?
O2 S1 C1 108.80(17) . . ?
N1 S1 C1 104.47(16) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.059
