# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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
_database_code_depnum_ccdc_archive 'CCDC 1007965'

_audit_update_record             
;
2014-06-12 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N2 O S'
_chemical_formula_sum            'C24 H26 N2 O S'
_chemical_formula_weight         390.53

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   16.4908(5)
_cell_length_b                   6.9106(3)
_cell_length_c                   18.7394(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2135.57(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    2038
_cell_measurement_theta_min      3.4860
_cell_measurement_theta_max      25.1430

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_T_min  0.96493
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Multi-scan absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            13243
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2021
_reflns_number_gt                1570
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    
;
 Superflip
                    Version: 04/17/13 12:45
Palatinus, L. & Chapuis, G.(2007): J. Appl. Cryst. 40, 786-790
              http://superspace.epfl.ch/superflip
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamong 3.2i'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0332P)²+0.5976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2021
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
O1 O 0.85945(10) 0.2500 0.28719(10) 0.0221(5) Uani 1 2 d S T P . .
C1 C 0.78714(16) 0.2500 0.25073(15) 0.0210(7) Uani 1 2 d S T P . .
C2 C 0.71653(17) 0.2500 0.28611(15) 0.0227(7) Uani 1 2 d S T P . .
H2 H 0.6674 0.2500 0.2596 0.027 Uiso 1 2 calc R U P . .
C3 C 0.71233(16) 0.2500 0.36267(14) 0.0194(6) Uani 1 2 d S T P . .
C4 C 0.78959(16) 0.2500 0.39768(15) 0.0207(7) Uani 1 2 d S T P . .
H4 H 0.7915 0.2500 0.4483 0.025 Uiso 1 2 calc R U P . .
C5 C 0.85931(16) 0.2500 0.36077(14) 0.0197(7) Uani 1 2 d S T P . .
C6 C 0.79776(16) 0.2500 0.17048(15) 0.0263(7) Uani 1 2 d S T P . .
C7 C 0.75732(13) 0.4308(3) 0.13901(11) 0.0354(6) Uani 1 1 d . . . . .
H7A H 0.7642 0.4311 0.0871 0.053 Uiso 1 1 calc R U . . .
H7B H 0.7826 0.5469 0.1592 0.053 Uiso 1 1 calc R U . . .
H7C H 0.6994 0.4300 0.1506 0.053 Uiso 1 1 calc R U . . .
C8 C 0.88764(19) 0.2500 0.15007(17) 0.0497(10) Uani 1 2 d S T P . .
H8A H 0.8928 0.2500 0.0980 0.075 Uiso 1 2 calc R U P . .
H8B H 0.9138 0.1342 0.1696 0.075 Uiso 0.5 1 calc R U P . .
H8C H 0.9138 0.3658 0.1696 0.075 Uiso 0.5 1 calc R U P . .
C9 C 0.94509(16) 0.2500 0.38929(15) 0.0243(7) Uani 1 2 d S T P . .
C10 C 0.94451(18) 0.2500 0.47092(15) 0.0320(8) Uani 1 2 d S T P . .
H10A H 1.0004 0.2500 0.4887 0.048 Uiso 1 2 calc R U P . .
H10B H 0.9164 0.1342 0.4882 0.048 Uiso 0.5 1 calc R U P . .
H10C H 0.9164 0.3658 0.4882 0.048 Uiso 0.5 1 calc R U P . .
C11 C 0.98974(12) 0.4310(3) 0.36214(12) 0.0345(6) Uani 1 1 d . . . . .
H11A H 1.0453 0.4315 0.3807 0.052 Uiso 1 1 calc R U . . .
H11B H 0.9613 0.5472 0.3786 0.052 Uiso 1 1 calc R U . . .
H11C H 0.9911 0.4295 0.3099 0.052 Uiso 1 1 calc R U . . .
C12 C 0.63856(16) 0.2500 0.39755(14) 0.0205(7) Uani 1 2 d S T P . .
H12 H 0.5915 0.2500 0.3683 0.025 Uiso 1 2 calc R U P . .
C13 C 0.62575(16) 0.2500 0.47151(15) 0.0207(6) Uani 1 2 d S T P . .
H13 H 0.6721 0.2500 0.5016 0.025 Uiso 1 2 calc R U P . .
C14 C 0.55095(17) 0.2500 0.50327(14) 0.0225(7) Uani 1 2 d S T P . .
H14 H 0.5048 0.2500 0.4729 0.027 Uiso 1 2 calc R U P . .
C15 C 0.53711(16) 0.2500 0.57701(14) 0.0213(7) Uani 1 2 d S T P . .
H15 H 0.5834 0.2500 0.6072 0.026 Uiso 1 2 calc R U P . .
C16 C 0.46276(16) 0.2500 0.60945(15) 0.0213(7) Uani 1 2 d S T P . .
C17 C 0.44461(17) 0.2500 0.68309(15) 0.0249(7) Uani 1 2 d S T P . .
H17 H 0.4856 0.2500 0.7187 0.030 Uiso 1 2 calc R U P . .
C18 C 0.36418(16) 0.2500 0.69924(15) 0.0228(7) Uani 1 2 d S T P . .
H18 H 0.3439 0.2500 0.7467 0.027 Uiso 1 2 calc R U P . .
C19 C 0.31381(16) 0.2500 0.63800(14) 0.0192(6) Uani 1 2 d S T P . .
S1 S 0.37152(4) 0.2500 0.56091(4) 0.0203(2) Uani 1 2 d S T P . .
C20 C 0.22959(16) 0.2500 0.63460(14) 0.0202(7) Uani 1 2 d S T P . .
C21 C 0.18067(17) 0.2500 0.69711(16) 0.0223(7) Uani 1 2 d S T P . .
N1 N 0.14000(15) 0.2500 0.74686(14) 0.0333(6) Uani 1 2 d S T P . .
C22 C 0.18883(17) 0.2500 0.56780(17) 0.0264(7) Uani 1 2 d S T P . .
N2 N 0.15681(15) 0.2500 0.51302(14) 0.0389(7) Uani 1 2 d S T P . .


_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
O1 C1 1.374(3) . ?
O1 C5 1.379(3) . ?
C1 C2 1.340(4) . ?
C1 C6 1.514(4) . ?
C2 C3 1.436(4) . ?
C2 H2 0.9500 . ?
C3 C12 1.381(4) . ?
C3 C4 1.433(4) . ?
C4 C5 1.342(4) . ?
C4 H4 0.9500 . ?
C5 C9 1.512(4) . ?
C6 C8 1.531(4) . ?
C6 C7 1.534(3) . ?
C6 C7 1.534(3) 7_565 ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.530(4) . ?
C9 C11 1.538(3) 7_565 ?
C9 C11 1.538(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.402(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.401(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.412(4) . ?
C16 S1 1.758(3) . ?
C17 C18 1.360(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.417(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(4) . ?
C19 S1 1.730(3) . ?
C20 C22 1.421(4) . ?
C20 C21 1.422(4) . ?
C21 N1 1.148(3) . ?
C22 N2 1.154(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
C1 O1 C5 119.7(2) . . ?
C2 C1 O1 120.5(2) . . ?
C2 C1 C6 126.3(2) . . ?
O1 C1 C6 113.2(2) . . ?
C1 C2 C3 122.4(3) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C12 C3 C4 124.5(3) . . ?
C12 C3 C2 121.0(3) . . ?
C4 C3 C2 114.5(2) . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 O1 121.1(2) . . ?
C4 C5 C9 128.3(2) . . ?
O1 C5 C9 110.6(2) . . ?
C1 C6 C8 111.1(2) . . ?
C1 C6 C7 109.36(16) . . ?
C8 C6 C7 108.95(16) . . ?
C1 C6 C7 109.36(16) . 7_565 ?
C8 C6 C7 108.95(16) . 7_565 ?
C7 C6 C7 109.1(2) . 7_565 ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 C10 110.3(2) . . ?
C5 C9 C11 109.33(15) . 7_565 ?
C10 C9 C11 109.50(16) . 7_565 ?
C5 C9 C11 109.33(15) . . ?
C10 C9 C11 109.50(16) . . ?
C11 C9 C11 108.8(2) 7_565 . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 C13 126.9(3) . . ?
C3 C12 H12 116.5 . . ?
C13 C12 H12 116.5 . . ?
C14 C13 C12 124.4(3) . . ?
C14 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C13 C14 C15 125.1(3) . . ?
C13 C14 H14 117.4 . . ?
C15 C14 H14 117.4 . . ?
C16 C15 C14 125.8(3) . . ?
C16 C15 H15 117.1 . . ?
C14 C15 H15 117.1 . . ?
C15 C16 C17 128.6(3) . . ?
C15 C16 S1 122.5(2) . . ?
C17 C16 S1 108.9(2) . . ?
C18 C17 C16 115.1(3) . . ?
C18 C17 H17 122.5 . . ?
C16 C17 H17 122.5 . . ?
C17 C18 C19 113.0(3) . . ?
C17 C18 H18 123.5 . . ?
C19 C18 H18 123.5 . . ?
C20 C19 C18 128.5(3) . . ?
C20 C19 S1 120.7(2) . . ?
C18 C19 S1 110.7(2) . . ?
C19 S1 C16 92.22(13) . . ?
C19 C20 C22 120.9(3) . . ?
C19 C20 C21 121.9(3) . . ?
C22 C20 C21 117.2(2) . . ?
N1 C21 C20 178.8(3) . . ?
N2 C22 C20 179.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 0.000(0) . . . . ?
C5 O1 C1 C6 180.000(0) . . . . ?
O1 C1 C2 C3 0.000(0) . . . . ?
C6 C1 C2 C3 180.000(0) . . . . ?
C1 C2 C3 C12 180.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C12 C3 C4 C5 180.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C3 C4 C5 O1 0.000(0) . . . . ?
C3 C4 C5 C9 180.000(0) . . . . ?
C1 O1 C5 C4 0.000(0) . . . . ?
C1 O1 C5 C9 180.000(0) . . . . ?
C2 C1 C6 C8 180.000(0) . . . . ?
O1 C1 C6 C8 0.000(0) . . . . ?
C2 C1 C6 C7 59.69(15) . . . . ?
O1 C1 C6 C7 -120.31(16) . . . . ?
C2 C1 C6 C7 -59.69(16) . . . 7_565 ?
O1 C1 C6 C7 120.31(15) . . . 7_565 ?
C4 C5 C9 C10 0.000(0) . . . . ?
O1 C5 C9 C10 180.000(0) . . . . ?
C4 C5 C9 C11 120.49(16) . . . 7_565 ?
O1 C5 C9 C11 -59.51(16) . . . 7_565 ?
C4 C5 C9 C11 -120.49(16) . . . . ?
O1 C5 C9 C11 59.51(16) . . . . ?
C4 C3 C12 C13 0.000(1) . . . . ?
C2 C3 C12 C13 180.000(0) . . . . ?
C3 C12 C13 C14 180.000(0) . . . . ?
C12 C13 C14 C15 180.000(0) . . . . ?
C13 C14 C15 C16 180.000(1) . . . . ?
C14 C15 C16 C17 180.000(1) . . . . ?
C14 C15 C16 S1 0.000(1) . . . . ?
C15 C16 C17 C18 180.000(1) . . . . ?
S1 C16 C17 C18 0.000(1) . . . . ?
C16 C17 C18 C19 0.000(1) . . . . ?
C17 C18 C19 C20 180.000(1) . . . . ?
C17 C18 C19 S1 0.000(1) . . . . ?
C20 C19 S1 C16 180.000(1) . . . . ?
C18 C19 S1 C16 0.000(0) . . . . ?
C15 C16 S1 C19 180.000(0) . . . . ?
C17 C16 S1 C19 0.000(1) . . . . ?
C18 C19 C20 C22 180.000(1) . . . . ?
S1 C19 C20 C22 0.000(1) . . . . ?
C18 C19 C20 C21 0.000(1) . . . . ?
S1 C19 C20 C21 180.000(1) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7B N1 0.98 2.59 3.508(3) 156.4 3_656
C10 H10A N2 0.98 2.62 3.589(4) 170.2 1_655
C14 H14 S1 0.95 2.75 3.150(3) 106.3 .
C17 H17 N1 0.95 2.63 3.479(4) 149.5 6_657

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_compound
_database_code_depnum_ccdc_archive 'CCDC 1007966'

_audit_update_record             
;
2014-06-12 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O S'
_chemical_formula_sum            'C22 H24 N2 O S'
_chemical_formula_weight         364.49

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   P21/m

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

_cell_length_a                   9.1986(13)
_cell_length_b                   6.8265(10)
_cell_length_c                   17.101(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.222(16)
_cell_angle_gamma                90.00
_cell_volume                     1036.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    660
_cell_measurement_theta_min      3.7560
_cell_measurement_theta_max      18.7210

_exptl_crystal_description       needle
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_correction_T_min  0.48650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Multi-scan absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_coefficient_mu    0.168



_exptl_special_details           ?

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measurement_method       ω-scans

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11105
_diffrn_reflns_av_R_equivalents  0.1603
_diffrn_reflns_av_sigmaI/netI    0.1485
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1945
_reflns_number_gt                1088
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    
;
Superflip
                    Version: 03/16/09 15:32
Palatinus, L. & Chapuis, G.(2007): J. Appl. Cryst. 40, 786-790
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond 3.2h'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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 > 2σ(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)+(0.0985P)²+0.4679P] 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         1945
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.1046
_refine_ls_wR_factor_ref         0.2475
_refine_ls_wR_factor_gt          0.2063
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
S1 S 0.9466(2) 0.2500 0.49163(12) 0.0338(6) Uani 1 2 d S . .
C1 C 1.1379(9) 0.2500 0.5391(5) 0.0349(19) Uani 1 2 d S . .
C2 C 1.2200(9) 0.2500 0.4816(5) 0.039(2) Uani 1 2 d S . .
H2 H 1.3270 0.2500 0.4953 0.046 Uiso 1 2 calc SR . .
C3 C 1.1312(10) 0.2500 0.4022(5) 0.043(2) Uani 1 2 d S . .
H3 H 1.1714 0.2500 0.3564 0.052 Uiso 1 2 calc SR . .
C4 C 0.9761(10) 0.2500 0.3964(5) 0.040(2) Uani 1 2 d S . .
C5 C 0.8649(11) 0.2500 0.3216(5) 0.048(2) Uani 1 2 d S . .
H5 H 0.9035 0.2500 0.2753 0.058 Uiso 1 2 calc SR . .
C6 C 0.7144(11) 0.2500 0.3050(5) 0.049(2) Uani 1 2 d S . .
C7 C 0.6251(10) 0.2500 0.2210(6) 0.046(2) Uani 1 2 d S . .
N1 N 0.5477(8) 0.2500 0.1580(4) 0.054(2) Uani 1 2 d S . .
C8 C 0.6343(10) 0.2500 0.3655(5) 0.053(2) Uani 1 2 d S . .
N2 N 0.5627(10) 0.2500 0.4137(5) 0.088(3) Uani 1 2 d S . .
C9 C 1.2015(8) 0.2500 0.6246(4) 0.0301(18) Uani 1 2 d S . .
H9 H 1.3085 0.2500 0.6407 0.036 Uiso 1 2 calc SR . .
C10 C 1.1362(8) 0.2500 0.6872(4) 0.0317(18) Uani 1 2 d S . .
C11 C 0.9794(9) 0.2500 0.6812(5) 0.0343(19) Uani 1 2 d S . .
H11 H 0.9103 0.2500 0.6290 0.041 Uiso 1 2 calc SR . .
C12 C 0.9262(9) 0.2500 0.7462(5) 0.040(2) Uani 1 2 d S . .
O1 O 1.0205(6) 0.2500 0.8235(3) 0.0428(14) Uani 1 2 d S . .
C13 C 1.1741(9) 0.2500 0.8336(4) 0.0339(18) Uani 1 2 d S . .
C14 C 1.2296(8) 0.2500 0.7704(4) 0.0329(19) Uani 1 2 d S . .
H14 H 1.3360 0.2500 0.7793 0.040 Uiso 1 2 calc SR . .
C15 C 0.7633(10) 0.2500 0.7490(5) 0.053(2) Uani 1 2 d S . .
C16 C 0.6595(10) 0.2500 0.6631(7) 0.095(4) Uani 1 2 d S . .
H16A H 0.5543 0.2500 0.6656 0.142 Uiso 1 2 calc SR . .
H16B H 0.6789 0.1328 0.6343 0.142 Uiso 0.50 1 calc PR . .
H16C H 0.6789 0.3672 0.6343 0.142 Uiso 0.50 1 calc PR . .
C17 C 0.7317(8) 0.4328(10) 0.7933(5) 0.083(2) Uani 1 1 d . . .
H17A H 0.6257 0.4336 0.7943 0.125 Uiso 1 1 calc R . .
H17B H 0.7530 0.5499 0.7650 0.125 Uiso 1 1 calc R . .
H17C H 0.7962 0.4324 0.8489 0.125 Uiso 1 1 calc R . .
C18 C 1.2544(9) 0.2500 0.9228(5) 0.047(2) Uani 1 2 d S . .
C19 C 1.2083(8) 0.4339(10) 0.9621(4) 0.072(2) Uani 1 1 d . . .
H19A H 1.2606 0.4358 1.0199 0.108 Uiso 1 1 calc R . .
H19B H 1.0992 0.4324 0.9555 0.108 Uiso 1 1 calc R . .
H19C H 1.2356 0.5509 0.9359 0.108 Uiso 1 1 calc R . .
C20 C 1.4227(9) 0.2500 0.9334(5) 0.048(2) Uani 1 2 d S . .
H20A H 1.4746 0.2500 0.9914 0.072 Uiso 1 2 calc SR . .
H20B H 1.4513 0.3672 0.9079 0.072 Uiso 0.50 1 calc PR . .
H20C H 1.4513 0.1328 0.9079 0.072 Uiso 0.50 1 calc PR . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C4 1.719(8) . ?
S1 C1 1.733(8) . ?
C1 C2 1.389(10) . ?
C1 C9 1.426(10) . ?
C2 C3 1.388(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(11) . ?
C5 C6 1.337(11) . ?
C5 H5 0.9500 . ?
C6 C8 1.420(12) . ?
C6 C7 1.455(12) . ?
C7 N1 1.125(9) . ?
C8 N2 1.182(11) . ?
C9 C10 1.357(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.419(10) . ?
C10 C14 1.457(10) . ?
C11 C12 1.327(10) . ?
C11 H11 0.9500 . ?
C12 O1 1.379(9) . ?
C12 C15 1.511(11) . ?
O1 C13 1.378(9) . ?
C13 C14 1.312(9) . ?
C13 C18 1.510(10) . ?
C14 H14 0.9500 . ?
C15 C17 1.527(7) . ?
C15 C17 1.527(7) 4_565 ?
C15 C16 1.528(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.511(10) . ?
C18 C19 1.535(7) . ?
C18 C19 1.535(7) 4_565 ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C4 S1 C1 92.9(4) . . ?
C2 C1 C9 125.0(7) . . ?
C2 C1 S1 110.0(6) . . ?
C9 C1 S1 125.0(6) . . ?
C3 C2 C1 113.7(8) . . ?
C3 C2 H2 123.1 . . ?
C1 C2 H2 123.1 . . ?
C2 C3 C4 113.3(7) . . ?
C2 C3 H3 123.4 . . ?
C4 C3 H3 123.4 . . ?
C3 C4 C5 123.0(8) . . ?
C3 C4 S1 110.1(6) . . ?
C5 C4 S1 126.9(7) . . ?
C6 C5 C4 131.0(9) . . ?
C6 C5 H5 114.5 . . ?
C4 C5 H5 114.5 . . ?
C5 C6 C8 123.4(9) . . ?
C5 C6 C7 119.7(8) . . ?
C8 C6 C7 116.9(8) . . ?
N1 C7 C6 175.3(10) . . ?
N2 C8 C6 177.6(10) . . ?
C10 C9 C1 131.4(7) . . ?
C10 C9 H9 114.3 . . ?
C1 C9 H9 114.3 . . ?
C9 C10 C11 126.5(7) . . ?
C9 C10 C14 120.0(7) . . ?
C11 C10 C14 113.4(6) . . ?
C12 C11 C10 122.1(8) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 O1 121.8(7) . . ?
C11 C12 C15 127.8(8) . . ?
O1 C12 C15 110.4(7) . . ?
C13 O1 C12 119.1(6) . . ?
C14 C13 O1 120.3(7) . . ?
C14 C13 C18 129.8(7) . . ?
O1 C13 C18 109.9(6) . . ?
C13 C14 C10 123.3(7) . . ?
C13 C14 H14 118.4 . . ?
C10 C14 H14 118.4 . . ?
C12 C15 C17 109.6(5) . . ?
C12 C15 C17 109.6(5) . 4_565 ?
C17 C15 C17 109.7(8) . 4_565 ?
C12 C15 C16 110.1(7) . . ?
C17 C15 C16 108.9(5) . . ?
C17 C15 C16 108.9(5) 4_565 . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 C20 109.6(6) . . ?
C13 C18 C19 108.9(5) . . ?
C20 C18 C19 109.9(5) . . ?
C13 C18 C19 108.9(5) . 4_565 ?
C20 C18 C19 109.9(5) . 4_565 ?
C19 C18 C19 109.7(7) . 4_565 ?
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 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C1 C2 0.000(2) . . . . ?
C4 S1 C1 C9 180.000(2) . . . . ?
C9 C1 C2 C3 180.000(3) . . . . ?
S1 C1 C2 C3 0.000(3) . . . . ?
C1 C2 C3 C4 0.000(2) . . . . ?
C2 C3 C4 C5 180.000(3) . . . . ?
C2 C3 C4 S1 0.000(2) . . . . ?
C1 S1 C4 C3 0.000(2) . . . . ?
C1 S1 C4 C5 180.000(2) . . . . ?
C3 C4 C5 C6 180.000(2) . . . . ?
S1 C4 C5 C6 0.000(3) . . . . ?
C4 C5 C6 C8 0.000(3) . . . . ?
C4 C5 C6 C7 180.000(2) . . . . ?
C2 C1 C9 C10 180.000(4) . . . . ?
S1 C1 C9 C10 0.000(4) . . . . ?
C1 C9 C10 C11 0.000(4) . . . . ?
C1 C9 C10 C14 180.000(4) . . . . ?
C9 C10 C11 C12 180.000(4) . . . . ?
C14 C10 C11 C12 0.000(4) . . . . ?
C10 C11 C12 O1 0.000(4) . . . . ?
C10 C11 C12 C15 180.000(4) . . . . ?
C11 C12 O1 C13 0.000(4) . . . . ?
C15 C12 O1 C13 180.000(4) . . . . ?
C12 O1 C13 C14 0.000(5) . . . . ?
C12 O1 C13 C18 180.000(4) . . . . ?
O1 C13 C14 C10 0.000(5) . . . . ?
C18 C13 C14 C10 180.000(4) . . . . ?
C9 C10 C14 C13 180.000(4) . . . . ?
C11 C10 C14 C13 0.000(4) . . . . ?
C11 C12 C15 C17 -119.8(5) . . . . ?
O1 C12 C15 C17 60.2(5) . . . . ?
C11 C12 C15 C17 119.8(5) . . . 4_565 ?
O1 C12 C15 C17 -60.2(5) . . . 4_565 ?
C11 C12 C15 C16 0.000(5) . . . . ?
O1 C12 C15 C16 180.000(4) . . . . ?
C14 C13 C18 C20 0.000(5) . . . . ?
O1 C13 C18 C20 180.000(4) . . . . ?
C14 C13 C18 C19 120.2(5) . . . . ?
O1 C13 C18 C19 -59.8(5) . . . . ?
C14 C13 C18 C19 -120.2(5) . . . 4_565 ?
O1 C13 C18 C19 59.8(5) . . . 4_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 S1 0.95 2.46 3.176(8) 132.3 .

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.073

