# Electronic Supplementary Material (ESI) for ChemComm.
# 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_u_tetragonal
_database_code_depnum_ccdc_archive 'CCDC 1030735'
_audit_update_record             
;
2014-11-01 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O2 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C22 H24 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         380.50
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_symmetry_Int_Tables_number      76

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -y,x,1/4+z
3 -x,-y,1/2+z
4 y,-x,3/4+z

_cell_length_a                   12.4405(5)
_cell_length_b                   12.4405(5)
_cell_length_c                   13.4141(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2076.05(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5371
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      30.4
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.141
_exptl_crystal_size_rad          0.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.174
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA, DIFABS, DELABS
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   ' multi-scan'
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_absorpt_correction_T_min  0.81454
_exptl_absorpt_correction_T_max  1.00000

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.0419

_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

# number of measured reflections (redundant set)
_diffrn_reflns_number            10114
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.7690
_diffrn_reflns_theta_max         30.4172
_diffrn_reflns_theta_full        25.0
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             5371
# number of observed reflections (> n sig(I))
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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     
'w=1/[σ²(Fo²)+(0.0367P)²+0.1440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 882 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5371
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031


#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
C22 C 0.6314(6) 0.4005(6) 0.2806(5) 0.136(3) Uani 1 1 d . . . . .
H22A H 0.6772 0.4104 0.3374 0.204 Uiso 1 1 calc R U . . .
H22B H 0.5837 0.3413 0.2925 0.204 Uiso 1 1 calc R U . . .
H22C H 0.5902 0.4647 0.2695 0.204 Uiso 1 1 calc R U . . .
H1N H 0.702(3) 0.554(3) 0.038(4) 0.065(13) Uiso 1 1 d . . . . .
S1 S 0.81000(17) 0.95162(14) 0.09197(15) 0.1212(7) Uani 1 1 d . . . . .
O1 O 0.5438(2) 0.6513(2) 0.0265(2) 0.0591(8) Uani 1 1 d . . . . .
C11 C 0.3451(3) 0.8807(4) 0.0187(3) 0.0597(11) Uani 1 1 d . . . . .
O2 O 0.5777(2) 0.6984(2) 0.18685(19) 0.0623(8) Uani 1 1 d . . . . .
N1 N 0.6943(3) 0.5956(3) 0.0962(2) 0.0547(9) Uani 1 1 d . . . . .
C15 C 0.6039(3) 0.6521(3) 0.1107(3) 0.0516(10) Uani 1 1 d . . . . .
C6 C 0.3232(4) 0.9274(3) -0.0733(4) 0.0612(11) Uani 1 1 d . . . . .
C5 C 0.4185(4) 0.9161(3) -0.1366(3) 0.0612(11) Uani 1 1 d . . . . .
C13 C 0.4969(4) 0.8590(3) -0.0842(3) 0.0570(11) Uani 1 1 d . . . . .
C1 C 0.5963(4) 0.8386(4) -0.1274(4) 0.0683(13) Uani 1 1 d . . . . .
H1 H 0.6489 0.8020 -0.0916 0.082 Uiso 1 1 calc R U . . .
C14 C 0.4421(3) 0.7080(3) 0.0331(3) 0.0597(11) Uani 1 1 d . . . . .
H14A H 0.4102 0.6947 0.0979 0.072 Uiso 1 1 calc R U . . .
H14B H 0.3935 0.6803 -0.0172 0.072 Uiso 1 1 calc R U . . .
C12 C 0.4556(3) 0.8293(3) 0.0183(3) 0.0540(10) Uani 1 1 d . . . . .
H12 H 0.5012 0.8602 0.0706 0.065 Uiso 1 1 calc R U . . .
C19 C 0.7942(3) 0.4529(3) 0.1813(4) 0.0656(12) Uani 1 1 d . . . . .
H19A H 0.8333 0.4340 0.1212 0.079 Uiso 1 1 calc R U . . .
H19B H 0.8419 0.4403 0.2374 0.079 Uiso 1 1 calc R U . . .
C16 C 0.7685(3) 0.5734(3) 0.1774(3) 0.0582(11) Uani 1 1 d . . . . .
H16 H 0.7347 0.5947 0.2404 0.070 Uiso 1 1 calc R U . . .
C4 C 0.4400(5) 0.9501(4) -0.2327(4) 0.0754(14) Uani 1 1 d . . . . .
H4 H 0.3879 0.9874 -0.2684 0.090 Uiso 1 1 calc R U . . .
N2 N 0.8538(4) 0.7492(4) 0.1547(4) 0.0959(16) Uani 1 1 d . . . . .
C18 C 0.8340(4) 0.8335(5) 0.1270(4) 0.0739(14) Uani 1 1 d . . . . .
C10 C 0.2693(4) 0.8825(4) 0.0936(4) 0.0749(14) Uani 1 1 d . . . . .
H10 H 0.2845 0.8527 0.1556 0.090 Uiso 1 1 calc R U . . .
C3 C 0.5390(5) 0.9287(4) -0.2761(4) 0.0815(15) Uani 1 1 d . . . . .
H3 H 0.5530 0.9521 -0.3407 0.098 Uiso 1 1 calc R U . . .
C20 C 0.6984(4) 0.3776(4) 0.1910(4) 0.0853(16) Uani 1 1 d . . . . .
H20 H 0.6527 0.3899 0.1326 0.102 Uiso 1 1 calc R U . . .
C17 C 0.8720(4) 0.6358(4) 0.1647(4) 0.0826(16) Uani 1 1 d . . . . .
H17A H 0.9178 0.6231 0.2220 0.099 Uiso 1 1 calc R U . . .
H17B H 0.9093 0.6098 0.1060 0.099 Uiso 1 1 calc R U . . .
C7 C 0.2243(5) 0.9735(4) -0.0914(5) 0.0857(16) Uani 1 1 d . . . . .
H7 H 0.2086 1.0034 -0.1532 0.103 Uiso 1 1 calc R U . . .
C8 C 0.1480(5) 0.9741(5) -0.0146(6) 0.0996(19) Uani 1 1 d . . . . .
H8 H 0.0812 1.0056 -0.0252 0.120 Uiso 1 1 calc R U . . .
C2 C 0.6171(5) 0.8728(4) -0.2242(4) 0.0827(15) Uani 1 1 d . . . . .
H2 H 0.6831 0.8582 -0.2538 0.099 Uiso 1 1 calc R U . . .
C9 C 0.1708(5) 0.9290(5) 0.0755(5) 0.0948(18) Uani 1 1 d . . . . .
H9 H 0.1191 0.9296 0.1255 0.114 Uiso 1 1 calc R U . . .
C21 C 0.7365(6) 0.2603(5) 0.1857(7) 0.146(3) Uani 1 1 d . . . . .
H21A H 0.7843 0.2517 0.1301 0.219 Uiso 1 1 calc R U . . .
H21B H 0.6755 0.2139 0.1774 0.219 Uiso 1 1 calc R U . . .
H21C H 0.7733 0.2420 0.2462 0.219 Uiso 1 1 calc R U . . .


_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
C22 C20 1.491(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
S1 C18 1.572(6) . ?
O1 C15 1.355(4) . ?
O1 C14 1.450(5) . ?
C11 C10 1.379(6) . ?
C11 C6 1.391(6) . ?
C11 C12 1.516(6) . ?
O2 C15 1.217(4) . ?
N1 C15 1.341(5) . ?
N1 C16 1.454(5) . ?
N1 H1N 0.94(5) . ?
C6 C7 1.379(6) . ?
C6 C5 1.464(6) . ?
C5 C4 1.382(6) . ?
C5 C13 1.397(6) . ?
C13 C1 1.389(6) . ?
C13 C12 1.514(6) . ?
C1 C2 1.391(7) . ?
C1 H1 0.9300 . ?
C14 C12 1.532(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 H12 0.9800 . ?
C19 C20 1.522(6) . ?
C19 C16 1.534(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 C17 1.513(6) . ?
C16 H16 0.9800 . ?
C4 C3 1.389(7) . ?
C4 H4 0.9300 . ?
N2 C18 1.139(6) . ?
N2 C17 1.435(7) . ?
C10 C9 1.377(7) . ?
C10 H10 0.9300 . ?
C3 C2 1.383(7) . ?
C3 H3 0.9300 . ?
C20 C21 1.535(8) . ?
C20 H20 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C7 C8 1.400(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(8) . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 O1 C14 115.3(3) . . ?
C10 C11 C6 120.4(4) . . ?
C10 C11 C12 129.0(5) . . ?
C6 C11 C12 110.6(4) . . ?
C15 N1 C16 121.5(3) . . ?
C15 N1 H1N 120(3) . . ?
C16 N1 H1N 116(3) . . ?
O2 C15 N1 126.5(4) . . ?
O2 C15 O1 123.7(4) . . ?
N1 C15 O1 109.7(4) . . ?
C7 C6 C11 120.2(5) . . ?
C7 C6 C5 131.4(5) . . ?
C11 C6 C5 108.4(4) . . ?
C4 C5 C13 119.3(5) . . ?
C4 C5 C6 131.9(5) . . ?
C13 C5 C6 108.8(4) . . ?
C1 C13 C5 120.4(4) . . ?
C1 C13 C12 129.5(4) . . ?
C5 C13 C12 110.1(4) . . ?
C13 C1 C2 119.9(5) . . ?
C13 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
O1 C14 C12 112.1(3) . . ?
O1 C14 H14A 109.2 . . ?
C12 C14 H14A 109.2 . . ?
O1 C14 H14B 109.2 . . ?
C12 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C13 C12 C11 102.0(4) . . ?
C13 C12 C14 113.3(3) . . ?
C11 C12 C14 108.4(3) . . ?
C13 C12 H12 110.9 . . ?
C11 C12 H12 110.9 . . ?
C14 C12 H12 110.9 . . ?
C20 C19 C16 116.2(4) . . ?
C20 C19 H19A 108.2 . . ?
C16 C19 H19A 108.2 . . ?
C20 C19 H19B 108.2 . . ?
C16 C19 H19B 108.2 . . ?
H19A C19 H19B 107.4 . . ?
N1 C16 C17 111.0(4) . . ?
N1 C16 C19 110.1(4) . . ?
C17 C16 C19 109.1(4) . . ?
N1 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
C19 C16 H16 108.8 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C18 N2 C17 165.8(6) . . ?
N2 C18 S1 177.7(5) . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C22 C20 C19 112.9(5) . . ?
C22 C20 C21 113.1(6) . . ?
C19 C20 C21 109.9(5) . . ?
C22 C20 H20 106.9 . . ?
C19 C20 H20 106.9 . . ?
C21 C20 H20 106.9 . . ?
N2 C17 C16 112.4(4) . . ?
N2 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
N2 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C6 C7 C8 118.6(5) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 120.6(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C8 C9 C10 121.0(6) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
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 . . ?

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
C16 N1 C15 O2 6.9(6) . . . . ?
C16 N1 C15 O1 -173.4(4) . . . . ?
C14 O1 C15 O2 -1.6(6) . . . . ?
C14 O1 C15 N1 178.7(3) . . . . ?
C10 C11 C6 C7 -1.8(7) . . . . ?
C12 C11 C6 C7 176.3(4) . . . . ?
C10 C11 C6 C5 178.5(4) . . . . ?
C12 C11 C6 C5 -3.5(5) . . . . ?
C7 C6 C5 C4 1.9(8) . . . . ?
C11 C6 C5 C4 -178.4(4) . . . . ?
C7 C6 C5 C13 -177.7(5) . . . . ?
C11 C6 C5 C13 2.1(5) . . . . ?
C4 C5 C13 C1 1.3(6) . . . . ?
C6 C5 C13 C1 -179.1(4) . . . . ?
C4 C5 C13 C12 -179.4(4) . . . . ?
C6 C5 C13 C12 0.2(5) . . . . ?
C5 C13 C1 C2 -1.5(7) . . . . ?
C12 C13 C1 C2 179.4(4) . . . . ?
C15 O1 C14 C12 81.7(4) . . . . ?
C1 C13 C12 C11 177.0(4) . . . . ?
C5 C13 C12 C11 -2.1(4) . . . . ?
C1 C13 C12 C14 -66.6(6) . . . . ?
C5 C13 C12 C14 114.2(4) . . . . ?
C10 C11 C12 C13 -178.7(5) . . . . ?
C6 C11 C12 C13 3.4(4) . . . . ?
C10 C11 C12 C14 61.5(6) . . . . ?
C6 C11 C12 C14 -116.3(4) . . . . ?
O1 C14 C12 C13 63.4(4) . . . . ?
O1 C14 C12 C11 175.8(3) . . . . ?
C15 N1 C16 C17 -110.1(4) . . . . ?
C15 N1 C16 C19 128.9(4) . . . . ?
C20 C19 C16 N1 -56.2(5) . . . . ?
C20 C19 C16 C17 -178.3(4) . . . . ?
C13 C5 C4 C3 -0.7(7) . . . . ?
C6 C5 C4 C3 179.8(5) . . . . ?
C6 C11 C10 C9 1.4(7) . . . . ?
C12 C11 C10 C9 -176.2(5) . . . . ?
C5 C4 C3 C2 0.3(8) . . . . ?
C16 C19 C20 C22 -57.2(6) . . . . ?
C16 C19 C20 C21 175.6(5) . . . . ?
C18 N2 C17 C16 -79(2) . . . . ?
N1 C16 C17 N2 55.2(6) . . . . ?
C19 C16 C17 N2 176.7(4) . . . . ?
C11 C6 C7 C8 1.4(7) . . . . ?
C5 C6 C7 C8 -178.9(5) . . . . ?
C6 C7 C8 C9 -0.8(9) . . . . ?
C4 C3 C2 C1 -0.5(8) . . . . ?
C13 C1 C2 C3 1.1(7) . . . . ?
C7 C8 C9 C10 0.5(10) . . . . ?
C11 C10 C9 C8 -0.8(9) . . . . ?


#===END
####################################################################### 
# 
# 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_redo
_database_code_depnum_ccdc_archive 'CCDC 1030363'
_audit_update_record             
;
2014-11-01 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O2 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C22 H24 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         380.50
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_symmetry_Int_Tables_number      76

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -y,x,1/4+z
3 -x,-y,1/2+z
4 y,-x,3/4+z

_cell_length_a                   17.4665(1)
_cell_length_b                   17.4665(1)
_cell_length_c                   13.1291(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4005.41(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    42280
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      50.1
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.5992
_exptl_crystal_size_mid          0.3100
_exptl_crystal_size_min          0.2556
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.181
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   gaussian
# Example: '(North et al., 1968)'
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  1.843

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'fω scans'
_diffrn_detector_area_resol_mean 18.4


# number of measured reflections (redundant set)
_diffrn_reflns_number            530944
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.6076
_diffrn_reflns_theta_max         50.5794
_diffrn_measured_fraction_theta_max 0.9998
_diffrn_reflns_theta_full        26.3154
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             42280
# number of observed reflections (> n sig(I))
_reflns_number_gt                32688
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     
'W=1/[Σ²(FO²)+(0.0262P)²] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed


# Permitted for _refine_ls_hydrogen_treatment :
# refall  - refined all H parameters
# refxyz  - refined H coordinates only
# refU    - refined H U only
# noref   - no refinement of H parameters
# constr  - H parameters constrained
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    ' mixed'

_refine_ls_extinction_method     ' none'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(12)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration unk

_refine_ls_number_reflns         42280
_refine_ls_number_parameters     499
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.046

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
C1 C 0.28023(4) -0.11164(4) 0.49709(7) 0.02066(11) Uani 1 1 d . . . . .
H1 H 0.2704 -0.0674 0.5343 0.025 Uiso 1 1 calc R U . . .
C1A C 0.63174(4) -0.21708(4) 0.73417(6) 0.02008(11) Uani 1 1 d . . . . .
H1A H 0.5854 -0.2212 0.7685 0.024 Uiso 1 1 calc R U . . .
C2 C 0.25184(5) -0.11986(5) 0.39786(7) 0.02461(13) Uani 1 1 d . . . . .
H2 H 0.2236 -0.0805 0.3685 0.030 Uiso 1 1 calc R U . . .
C2A C 0.63962(5) -0.24548(5) 0.63509(7) 0.02271(12) Uani 1 1 d . . . . .
H2A H 0.5980 -0.2683 0.6031 0.027 Uiso 1 1 calc R U . . .
C3 C 0.26569(5) -0.18689(6) 0.34272(7) 0.02469(13) Uani 1 1 d . . . . .
H3 H 0.2466 -0.1915 0.2769 0.030 Uiso 1 1 calc R U . . .
C3A C 0.70962(5) -0.23983(5) 0.58375(6) 0.02246(12) Uani 1 1 d . . . . .
H3A H 0.7139 -0.2590 0.5179 0.027 Uiso 1 1 calc R U . . .
C4 C 0.30785(5) -0.24723(5) 0.38500(6) 0.02169(12) Uani 1 1 d . . . . .
H4 H 0.3163 -0.2920 0.3484 0.026 Uiso 1 1 calc R U . . .
C4A C 0.77319(5) -0.20582(4) 0.63013(6) 0.02026(11) Uani 1 1 d . . . . .
H4A H 0.8198 -0.2025 0.5961 0.024 Uiso 1 1 calc R U . . .
C5 C 0.33701(4) -0.23851(4) 0.48347(6) 0.01737(9) Uani 1 1 d . . . . .
C5A C 0.76514(4) -0.17685(4) 0.72887(5) 0.01658(9) Uani 1 1 d . . . . .
C6 C 0.38286(4) -0.29070(4) 0.54664(6) 0.01759(9) Uani 1 1 d . . . . .
C6A C 0.82028(4) -0.13776(4) 0.79544(6) 0.01731(9) Uani 1 1 d . . . . .
C7 C 0.41222(5) -0.36364(4) 0.52658(7) 0.02291(12) Uani 1 1 d . . . . .
H7 H 0.4048 -0.3866 0.4635 0.027 Uiso 1 1 calc R U . . .
C7A C 0.89672(4) -0.11735(5) 0.77973(7) 0.02316(13) Uani 1 1 d . . . . .
H7A H 0.9210 -0.1282 0.7184 0.028 Uiso 1 1 calc R U . . .
C8 C 0.45290(5) -0.40122(5) 0.60323(9) 0.02659(15) Uani 1 1 d . . . . .
H8 H 0.4725 -0.4498 0.5910 0.032 Uiso 1 1 calc R U . . .
C8A C 0.93592(5) -0.08024(6) 0.85826(9) 0.02712(15) Uani 1 1 d . . . . .
H8A H 0.9869 -0.0664 0.8489 0.033 Uiso 1 1 calc R U . . .
C9 C 0.46458(5) -0.36680(5) 0.69823(8) 0.02569(14) Uani 1 1 d . . . . .
H9 H 0.4916 -0.3928 0.7485 0.031 Uiso 1 1 calc R U . . .
C9A C 0.89982(5) -0.06357(5) 0.95064(8) 0.02612(14) Uani 1 1 d . . . . .
H9A H 0.9268 -0.0387 1.0019 0.031 Uiso 1 1 calc R U . . .
C10 C 0.43578(5) -0.29338(4) 0.71811(7) 0.02141(11) Uani 1 1 d . . . . .
H10 H 0.4436 -0.2703 0.7811 0.026 Uiso 1 1 calc R U . . .
C10A C 0.82319(4) -0.08411(5) 0.96657(6) 0.02101(11) Uani 1 1 d . . . . .
H10A H 0.7990 -0.0731 1.0280 0.025 Uiso 1 1 calc R U . . .
C11 C 0.39522(4) -0.25560(4) 0.64194(6) 0.01722(9) Uani 1 1 d . . . . .
C11A C 0.78395(4) -0.12128(4) 0.88853(5) 0.01653(9) Uani 1 1 d . . . . .
C12 C 0.36160(4) -0.17546(4) 0.64258(6) 0.01648(9) Uani 1 1 d . . . . .
H12 H 0.3238 -0.1700 0.6973 0.020 Uiso 1 1 calc R U . . .
C12A C 0.70092(4) -0.14708(4) 0.88583(5) 0.01559(8) Uani 1 1 d . . . . .
H12A H 0.6914 -0.1857 0.9385 0.019 Uiso 1 1 calc R U . . .
C13 C 0.32340(4) -0.17090(4) 0.53904(6) 0.01682(9) Uani 1 1 d . . . . .
C13A C 0.69459(4) -0.18249(4) 0.78051(5) 0.01603(9) Uani 1 1 d . . . . .
C14 C 0.42657(4) -0.11700(4) 0.65500(6) 0.01706(9) Uani 1 1 d . . . . .
H14A H 0.4515 -0.1250 0.7201 0.020 Uiso 1 1 calc R U . . .
H14B H 0.4643 -0.1250 0.6018 0.020 Uiso 1 1 calc R U . . .
C14A C 0.64910(4) -0.07721(4) 0.90184(5) 0.01669(9) Uani 1 1 d . . . . .
H14C H 0.6588 -0.0559 0.9688 0.020 Uiso 1 1 calc R U . . .
H14D H 0.6619 -0.0384 0.8518 0.020 Uiso 1 1 calc R U . . .
C15 C 0.37116(4) -0.01039(4) 0.73800(5) 0.01428(8) Uani 1 1 d . . . . .
C15A C 0.53748(3) -0.12927(4) 0.97638(5) 0.01414(8) Uani 1 1 d . . . . .
C16 C 0.32811(4) 0.11154(4) 0.81018(5) 0.01575(9) Uani 1 1 d . . . . .
H16 H 0.3413 0.0849 0.8735 0.019 Uiso 1 1 calc R U . . .
C16A C 0.41324(4) -0.16900(4) 1.04430(5) 0.01497(8) Uani 1 1 d . . . . .
H16A H 0.4428 -0.1675 1.1077 0.018 Uiso 1 1 calc R U . . .
C17 C 0.24213(4) 0.13001(4) 0.81069(8) 0.02227(12) Uani 1 1 d . . . . .
H17A H 0.2297 0.1583 0.8721 0.027 Uiso 1 1 calc R U . . .
H17B H 0.2301 0.1623 0.7527 0.027 Uiso 1 1 calc R U . . .
C17A C 0.38654(4) -0.25160(4) 1.02555(7) 0.02047(11) Uani 1 1 d . . . . .
H17C H 0.3559 -0.2685 1.0829 0.025 Uiso 1 1 calc R U . . .
H17D H 0.3545 -0.2530 0.9652 0.025 Uiso 1 1 calc R U . . .
C18 C 0.16885(4) 0.01052(5) 0.76048(6) 0.02069(11) Uani 1 1 d . . . . .
C18A C 0.50351(5) -0.33860(5) 0.99195(6) 0.02096(11) Uani 1 1 d . . . . .
C19 C 0.37305(4) 0.18674(4) 0.80494(6) 0.01694(9) Uani 1 1 d . . . . .
H19A H 0.3580 0.2140 0.7438 0.020 Uiso 1 1 calc R U . . .
H19B H 0.3589 0.2182 0.8629 0.020 Uiso 1 1 calc R U . . .
C19A C 0.34331(4) -0.11685(4) 1.05585(6) 0.01696(9) Uani 1 1 d . . . . .
H19C H 0.3123 -0.1355 1.1119 0.020 Uiso 1 1 calc R U . . .
H19D H 0.3127 -0.1203 0.9944 0.020 Uiso 1 1 calc R U . . .
C20 C 0.46018(4) 0.17712(4) 0.80431(6) 0.01736(9) Uani 1 1 d . . . . .
H20 H 0.4736 0.1438 0.7470 0.021 Uiso 1 1 calc R U . . .
C20A C 0.36278(4) -0.03249(4) 1.07517(6) 0.01883(10) Uani 1 1 d . . . . .
H20A H 0.3915 -0.0136 1.0162 0.023 Uiso 1 1 calc R U . . .
C21 C 0.48961(5) 0.13955(6) 0.90169(7) 0.02745(15) Uani 1 1 d . . . . .
H21A H 0.5445 0.1374 0.9000 0.041 Uiso 1 1 calc R U . . .
H21B H 0.4694 0.0886 0.9068 0.041 Uiso 1 1 calc R U . . .
H21C H 0.4734 0.1690 0.9596 0.041 Uiso 1 1 calc R U . . .
C21A C 0.41301(6) -0.02222(5) 1.16975(7) 0.02564(14) Uani 1 1 d . . . . .
H21D H 0.4183 0.0313 1.1846 0.038 Uiso 1 1 calc R U . . .
H21E H 0.4626 -0.0440 1.1573 0.038 Uiso 1 1 calc R U . . .
H21F H 0.3896 -0.0476 1.2267 0.038 Uiso 1 1 calc R U . . .
C22 C 0.49840(5) 0.25481(5) 0.78668(8) 0.02584(14) Uani 1 1 d . . . . .
H22A H 0.4792 0.2770 0.7249 0.039 Uiso 1 1 calc R U . . .
H22B H 0.5528 0.2480 0.7813 0.039 Uiso 1 1 calc R U . . .
H22C H 0.4872 0.2882 0.8428 0.039 Uiso 1 1 calc R U . . .
C22A C 0.28928(6) 0.01443(5) 1.08358(10) 0.02989(17) Uani 1 1 d . . . . .
H22D H 0.2591 0.0075 1.0231 0.045 Uiso 1 1 calc R U . . .
H22E H 0.3019 0.0676 1.0911 0.045 Uiso 1 1 calc R U . . .
H22F H 0.2606 -0.0023 1.1418 0.045 Uiso 1 1 calc R U . . .
N1 N 0.34806(3) 0.06284(3) 0.72397(5) 0.01555(8) Uani 1 1 d . . . . .
N1A N 0.46187(3) -0.14240(4) 0.96125(4) 0.01563(8) Uani 1 1 d . . . . .
N2 N 0.19622(4) 0.06175(5) 0.80629(7) 0.02521(12) Uani 1 1 d . . . . .
N2A N 0.44948(5) -0.30255(4) 1.01241(8) 0.02627(13) Uani 1 1 d . . . . .
O1 O 0.39878(3) -0.03944(3) 0.64971(4) 0.01694(7) Uani 1 1 d . . . . .
O1A O 0.56875(3) -0.09548(3) 0.89326(4) 0.01687(7) Uani 1 1 d . . . . .
O2 O 0.36755(4) -0.04647(3) 0.81786(4) 0.01862(8) Uani 1 1 d . . . . .
O2A O 0.57380(3) -0.14593(3) 1.05305(4) 0.01768(8) Uani 1 1 d . . . . .
S1 S 0.12832(2) -0.05973(2) 0.70528(2) 0.02931(5) Uani 1 1 d . . . . .
S1A S 0.57631(2) -0.39066(2) 0.96681(3) 0.03741(6) Uani 1 1 d . . . . .
H1N H 0.3623(10) 0.0850(10) 0.6682(14) 0.023(3) Uiso 1 1 d . . . . .
H1NA H 0.4412(8) -0.1194(8) 0.9130(11) 0.012(3) Uiso 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 C13 1.3940(10) . ?
C1 C2 1.4013(13) . ?
C1A C13A 1.3929(10) . ?
C1A C2A 1.3990(12) . ?
C2 C3 1.3977(14) . ?
C2A C3A 1.3996(13) . ?
C3 C4 1.4003(13) . ?
C3A C4A 1.3989(13) . ?
C4 C5 1.3977(11) . ?
C4A C5A 1.3986(10) . ?
C5 C13 1.4084(10) . ?
C5 C6 1.4698(11) . ?
C5A C13A 1.4099(9) . ?
C5A C6A 1.4688(10) . ?
C6 C7 1.3984(10) . ?
C6 C11 1.4099(10) . ?
C6A C7A 1.3972(10) . ?
C6A C11A 1.4069(10) . ?
C7 C8 1.3958(14) . ?
C7A C8A 1.3972(14) . ?
C8 C9 1.3995(15) . ?
C8A C9A 1.3977(15) . ?
C9 C10 1.4019(12) . ?
C9A C10A 1.4014(11) . ?
C10 C11 1.3920(11) . ?
C10A C11A 1.3932(10) . ?
C11 C12 1.5180(9) . ?
C11A C12A 1.5190(9) . ?
C12 C13 1.5164(10) . ?
C12 C14 1.5353(9) . ?
C12A C13A 1.5188(10) . ?
C12A C14A 1.5339(9) . ?
C14 O1 1.4407(9) . ?
C14A O1A 1.4436(8) . ?
C15 O2 1.2248(8) . ?
C15 N1 1.3539(8) . ?
C15 O1 1.3542(8) . ?
C15A O2A 1.2249(8) . ?
C15A N1A 1.3550(8) . ?
C15A O1A 1.3557(8) . ?
C16 N1 1.4581(9) . ?
C16 C19 1.5317(9) . ?
C16 C17 1.5359(10) . ?
C16A N1A 1.4582(9) . ?
C16A C19A 1.5312(9) . ?
C16A C17A 1.5361(10) . ?
C17 N2 1.4380(11) . ?
C17A N2A 1.4249(10) . ?
C18 N2 1.1794(11) . ?
C18 S1 1.5912(9) . ?
C18A N2A 1.1657(11) . ?
C18A S1A 1.5978(8) . ?
C19 C20 1.5311(10) . ?
C19A C20A 1.5333(10) . ?
C20 C21 1.5262(11) . ?
C20 C22 1.5299(11) . ?
C20A C22A 1.5270(11) . ?
C20A C21A 1.5309(12) . ?

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
C13 C1 C2 118.87(7) . . ?
C13A C1A C2A 118.84(7) . . ?
C3 C2 C1 120.40(8) . . ?
C1A C2A C3A 120.58(7) . . ?
C2 C3 C4 121.07(8) . . ?
C4A C3A C2A 120.91(7) . . ?
C5 C4 C3 118.44(8) . . ?
C5A C4A C3A 118.51(7) . . ?
C4 C5 C13 120.59(7) . . ?
C4 C5 C6 130.76(7) . . ?
C13 C5 C6 108.64(6) . . ?
C4A C5A C13A 120.55(7) . . ?
C4A C5A C6A 130.82(7) . . ?
C13A C5A C6A 108.63(6) . . ?
C7 C6 C11 120.48(7) . . ?
C7 C6 C5 131.19(7) . . ?
C11 C6 C5 108.33(6) . . ?
C7A C6A C11A 120.46(7) . . ?
C7A C6A C5A 131.10(7) . . ?
C11A C6A C5A 108.44(6) . . ?
C8 C7 C6 118.63(8) . . ?
C8A C7A C6A 118.54(8) . . ?
C7 C8 C9 120.98(8) . . ?
C7A C8A C9A 121.06(7) . . ?
C8 C9 C10 120.43(8) . . ?
C8A C9A C10A 120.47(8) . . ?
C11 C10 C9 118.85(8) . . ?
C11A C10A C9A 118.64(8) . . ?
C10 C11 C6 120.62(7) . . ?
C10 C11 C12 129.05(7) . . ?
C6 C11 C12 110.29(6) . . ?
C10A C11A C6A 120.82(6) . . ?
C10A C11A C12A 128.69(7) . . ?
C6A C11A C12A 110.46(6) . . ?
C13 C12 C11 102.33(6) . . ?
C13 C12 C14 112.67(6) . . ?
C11 C12 C14 109.15(6) . . ?
C13A C12A C11A 102.22(5) . . ?
C13A C12A C14A 113.94(5) . . ?
C11A C12A C14A 108.91(5) . . ?
C1 C13 C5 120.61(7) . . ?
C1 C13 C12 129.14(7) . . ?
C5 C13 C12 110.25(6) . . ?
C1A C13A C5A 120.60(7) . . ?
C1A C13A C12A 129.17(6) . . ?
C5A C13A C12A 110.22(6) . . ?
O1 C14 C12 111.79(6) . . ?
O1A C14A C12A 112.77(5) . . ?
O2 C15 N1 125.96(6) . . ?
O2 C15 O1 123.94(6) . . ?
N1 C15 O1 110.10(6) . . ?
O2A C15A N1A 125.81(6) . . ?
O2A C15A O1A 123.80(6) . . ?
N1A C15A O1A 110.39(6) . . ?
N1 C16 C19 110.05(6) . . ?
N1 C16 C17 111.08(6) . . ?
C19 C16 C17 108.74(6) . . ?
N1A C16A C19A 110.43(5) . . ?
N1A C16A C17A 110.87(6) . . ?
C19A C16A C17A 109.41(5) . . ?
N2 C17 C16 111.77(6) . . ?
N2A C17A C16A 111.82(6) . . ?
N2 C18 S1 176.07(8) . . ?
N2A C18A S1A 177.71(9) . . ?
C20 C19 C16 114.56(5) . . ?
C16A C19A C20A 114.27(6) . . ?
C21 C20 C22 111.17(7) . . ?
C21 C20 C19 112.18(7) . . ?
C22 C20 C19 109.71(6) . . ?
C22A C20A C21A 111.12(7) . . ?
C22A C20A C19A 109.95(7) . . ?
C21A C20A C19A 111.95(7) . . ?
C15 N1 C16 121.12(6) . . ?
C15A N1A C16A 120.79(6) . . ?
C18 N2 C17 151.11(10) . . ?
C18A N2A C17A 171.78(10) . . ?
C15 O1 C14 115.54(5) . . ?
C15A O1A C14A 115.16(5) . . ?


#===END
####################################################################### 
# 
# 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 1030364'
_audit_update_record             
;
2014-11-01 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O2 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C22 H24 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         380.50
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   4.9386(3)
_cell_length_b                   15.0974(9)
_cell_length_c                   13.3932(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.286(7)
_cell_angle_gamma                90
_cell_volume                     990.53(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3881
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      26.0
_cell_special_details            
;
 
;

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.072
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.183
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.38997
_exptl_absorpt_correction_T_max  1.00000

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'fω scans'
_diffrn_detector_area_resol_mean 18.4

# number of measured reflections (redundant set)
_diffrn_reflns_number            7233
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3881
# number of observed reflections (> n sig(I))
_reflns_number_gt                2762
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     
'W=1/[Σ²(FO²)+(0.0262P)²] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed


# Permitted for _refine_ls_hydrogen_treatment :
# refall  - refined all H parameters
# refxyz  - refined H coordinates only
# refU    - refined H U only
# noref   - no refinement of H parameters
# constr  - H parameters constrained
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(10)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration syn

_refine_ls_number_reflns         3881
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.044

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S Uani 0.7087(4) 0.66048(11) 0.25233(14) 1.000 0.0639(7) . .
O1 O Uani 0.2593(6) 0.8688(2) 0.1281(2) 1.000 0.0242(11) . .
O2 O Uani 0.6307(6) 0.8988(2) 0.2413(2) 1.000 0.0268(11) . .
N1 N Uani 0.2116(8) 0.8706(3) 0.2900(3) 1.000 0.0245(12) . .
N2 N Uani 0.4571(9) 0.7270(3) 0.4071(4) 1.000 0.0443(19) . .
C1 C Uani 0.0348(10) 0.7013(3) 0.0093(4) 1.000 0.0301(17) . .
C2 C Uani -0.0104(10) 0.6114(3) -0.0095(4) 1.000 0.0326(17) . .
C3 C Uani 0.1049(11) 0.5689(4) -0.0856(4) 1.000 0.0355(19) . .
C4 C Uani 0.2738(9) 0.6135(3) -0.1439(4) 1.000 0.0295(17) . .
C5 C Uani 0.3178(10) 0.7039(3) -0.1261(4) 1.000 0.0278(17) . .
C6 C Uani 0.4774(10) 0.7689(4) -0.1760(4) 1.000 0.0285(17) . .
C7 C Uani 0.6392(10) 0.7580(4) -0.2527(4) 1.000 0.0354(19) . .
C8 C Uani 0.7717(11) 0.8317(4) -0.2855(4) 1.000 0.0377(19) . .
C9 C Uani 0.7443(10) 0.9144(4) -0.2430(4) 1.000 0.0356(17) . .
C10 C Uani 0.5797(10) 0.9252(4) -0.1660(4) 1.000 0.0332(17) . .
C11 C Uani 0.4495(9) 0.8522(3) -0.1333(4) 1.000 0.0249(17) . .
C12 C Uani 0.2738(9) 0.8454(3) -0.0484(4) 1.000 0.0250(17) . .
C13 C Uani 0.1989(9) 0.7467(3) -0.0503(4) 1.000 0.0250(17) . .
C14 C Uani 0.4339(9) 0.8759(3) 0.0487(4) 1.000 0.0271(17) . .
C15 C Uani 0.3888(10) 0.8813(3) 0.2221(4) 1.000 0.0245(16) . .
C16 C Uani 0.2979(10) 0.8816(3) 0.3975(4) 1.000 0.0269(16) . .
C17 C Uani 0.2843(11) 0.7911(4) 0.4484(4) 1.000 0.0374(17) . .
C18 C Uani 0.5570(12) 0.7007(4) 0.3384(5) 1.000 0.040(2) . .
C19 C Uani 0.1292(10) 0.9520(3) 0.4453(4) 1.000 0.0276(17) . .
C20 C Uani 0.2493(11) 0.9688(4) 0.5543(4) 1.000 0.042(2) . .
C21 C Uani 0.1172(11) 1.0371(3) 0.3823(4) 1.000 0.0361(19) . .
C22 C Uani -0.0491(10) 1.1110(4) 0.4228(4) 1.000 0.0431(19) . .
H1 H Uiso -0.04410 0.73060 0.06130 1.000 0.0360 calc .
H1N H Uiso 0.015(11) 0.864(4) 0.264(4) 1.000 0.062(18) . .
H2 H Uiso -0.12170 0.57880 0.03030 1.000 0.0390 calc .
H3 H Uiso 0.06750 0.50790 -0.09800 1.000 0.0430 calc .
H4 H Uiso 0.35690 0.58360 -0.19450 1.000 0.0350 calc .
H7 H Uiso 0.65890 0.70140 -0.28210 1.000 0.0420 calc .
H8 H Uiso 0.88290 0.82530 -0.33800 1.000 0.0450 calc .
H9 H Uiso 0.83730 0.96390 -0.26610 1.000 0.0430 calc .
H10 H Uiso 0.55850 0.98180 -0.13690 1.000 0.0400 calc .
H12 H Uiso 0.10540 0.88220 -0.06410 1.000 0.0300 calc .
H14A H Uiso 0.59850 0.83860 0.06500 1.000 0.0330 calc .
H14B H Uiso 0.49300 0.93810 0.04230 1.000 0.0330 calc .
H16 H Uiso 0.49280 0.90140 0.40640 1.000 0.0320 calc .
H17A H Uiso 0.34270 0.79740 0.52160 1.000 0.0450 calc .
H17B H Uiso 0.09340 0.76970 0.43920 1.000 0.0450 calc .
H19 H Uiso -0.06090 0.92900 0.44480 1.000 0.0330 calc .
H20A H Uiso 0.43370 0.99320 0.55620 1.000 0.0620 calc .
H20B H Uiso 0.25750 0.91290 0.59190 1.000 0.0620 calc .
H20C H Uiso 0.13370 1.01100 0.58500 1.000 0.0620 calc .
H21A H Uiso 0.30550 1.05860 0.37970 1.000 0.0440 calc .
H21B H Uiso 0.03680 1.02310 0.31260 1.000 0.0440 calc .
H22A H Uiso -0.23140 1.08880 0.43110 1.000 0.0650 calc .
H22B H Uiso -0.06570 1.16070 0.37530 1.000 0.0650 calc .
H22C H Uiso 0.04290 1.13110 0.48800 1.000 0.0650 calc .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C18 1.574(7) . . yes
O1 C14 1.456(6) . . yes
O1 C15 1.351(6) . . yes
O2 C15 1.219(6) . . yes
N1 C15 1.349(7) . . yes
N1 C16 1.458(7) . . yes
N2 C17 1.446(7) . . yes
N2 C18 1.167(8) . . yes
N1 H1N 0.99(5) . . no
C1 C13 1.389(7) . . no
C1 C2 1.393(6) . . no
C2 C3 1.386(7) . . no
C3 C4 1.387(7) . . no
C4 C5 1.398(6) . . no
C5 C6 1.471(7) . . no
C5 C13 1.394(7) . . no
C6 C11 1.396(8) . . no
C6 C7 1.389(7) . . no
C7 C8 1.390(8) . . no
C8 C9 1.386(8) . . no
C9 C10 1.401(7) . . no
C10 C11 1.375(7) . . no
C11 C12 1.519(7) . . no
C12 C14 1.506(7) . . no
C12 C13 1.535(6) . . no
C16 C17 1.532(8) . . no
C16 C19 1.539(7) . . no
C19 C21 1.534(7) . . no
C19 C20 1.526(8) . . no
C21 C22 1.525(7) . . no
C1 H1 0.9500 . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C12 H12 1.0000 . . no
C14 H14A 0.9900 . . no
C14 H14B 0.9900 . . no
C16 H16 1.0000 . . no
C17 H17A 0.9900 . . no
C17 H17B 0.9900 . . no
C19 H19 1.0000 . . no
C20 H20A 0.9800 . . no
C20 H20B 0.9800 . . no
C20 H20C 0.9800 . . no
C21 H21A 0.9900 . . no
C21 H21B 0.9900 . . no
C22 H22A 0.9800 . . no
C22 H22B 0.9800 . . no
C22 H22C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 C15 114.6(4) . . . yes
C15 N1 C16 121.2(4) . . . yes
C17 N2 C18 149.1(6) . . . yes
C16 N1 H1N 121(3) . . . no
C15 N1 H1N 118(3) . . . no
C2 C1 C13 118.0(5) . . . no
C1 C2 C3 120.8(5) . . . no
C2 C3 C4 121.4(5) . . . no
C3 C4 C5 118.0(5) . . . no
C4 C5 C6 130.9(5) . . . no
C6 C5 C13 108.7(4) . . . no
C4 C5 C13 120.4(4) . . . no
C7 C6 C11 120.4(5) . . . no
C5 C6 C11 109.2(4) . . . no
C5 C6 C7 130.4(5) . . . no
C6 C7 C8 118.5(5) . . . no
C7 C8 C9 121.1(5) . . . no
C8 C9 C10 120.2(5) . . . no
C9 C10 C11 118.7(5) . . . no
C10 C11 C12 128.8(4) . . . no
C6 C11 C10 121.2(5) . . . no
C6 C11 C12 110.0(4) . . . no
C11 C12 C13 102.3(4) . . . no
C11 C12 C14 109.8(4) . . . no
C13 C12 C14 114.2(4) . . . no
C1 C13 C5 121.4(4) . . . no
C5 C13 C12 109.8(4) . . . no
C1 C13 C12 128.8(4) . . . no
O1 C14 C12 108.3(4) . . . yes
O1 C15 N1 109.9(4) . . . yes
O1 C15 O2 124.2(4) . . . yes
O2 C15 N1 125.9(5) . . . yes
N1 C16 C19 112.6(4) . . . yes
N1 C16 C17 108.3(4) . . . yes
C17 C16 C19 112.0(4) . . . no
N2 C17 C16 111.4(4) . . . yes
S1 C18 N2 175.1(6) . . . yes
C16 C19 C20 110.3(4) . . . no
C16 C19 C21 109.6(4) . . . no
C20 C19 C21 111.7(4) . . . no
C19 C21 C22 113.7(4) . . . no
C2 C1 H1 121.00 . . . no
C13 C1 H1 121.00 . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C3 C4 H4 121.00 . . . no
C5 C4 H4 121.00 . . . no
C6 C7 H7 121.00 . . . no
C8 C7 H7 121.00 . . . no
C7 C8 H8 119.00 . . . no
C9 C8 H8 119.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C9 C10 H10 121.00 . . . no
C11 C10 H10 121.00 . . . no
C11 C12 H12 110.00 . . . no
C13 C12 H12 110.00 . . . no
C14 C12 H12 110.00 . . . no
O1 C14 H14A 110.00 . . . no
O1 C14 H14B 110.00 . . . no
C12 C14 H14A 110.00 . . . no
C12 C14 H14B 110.00 . . . no
H14A C14 H14B 108.00 . . . no
N1 C16 H16 108.00 . . . no
C17 C16 H16 108.00 . . . no
C19 C16 H16 108.00 . . . no
N2 C17 H17A 109.00 . . . no
N2 C17 H17B 109.00 . . . no
C16 C17 H17A 109.00 . . . no
C16 C17 H17B 109.00 . . . no
H17A C17 H17B 108.00 . . . no
C16 C19 H19 108.00 . . . no
C20 C19 H19 108.00 . . . no
C21 C19 H19 108.00 . . . no
C19 C20 H20A 110.00 . . . no
C19 C20 H20B 110.00 . . . no
C19 C20 H20C 109.00 . . . no
H20A C20 H20B 109.00 . . . no
H20A C20 H20C 109.00 . . . no
H20B C20 H20C 109.00 . . . no
C19 C21 H21A 109.00 . . . no
C19 C21 H21B 109.00 . . . no
C22 C21 H21A 109.00 . . . no
C22 C21 H21B 109.00 . . . no
H21A C21 H21B 108.00 . . . no
C21 C22 H22A 110.00 . . . no
C21 C22 H22B 109.00 . . . no
C21 C22 H22C 109.00 . . . no
H22A C22 H22B 109.00 . . . no
H22A C22 H22C 109.00 . . . no
H22B C22 H22C 109.00 . . . no

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
C14 O1 C15 N1 -178.1(4) . . . . no
C15 O1 C14 C12 170.5(4) . . . . no
C14 O1 C15 O2 1.3(6) . . . . no
C16 N1 C15 O1 -179.2(4) . . . . no
C15 N1 C16 C19 123.0(5) . . . . no
C16 N1 C15 O2 1.5(7) . . . . no
C15 N1 C16 C17 -112.7(5) . . . . no
C18 N2 C17 C16 -31.5(12) . . . . no
C2 C1 C13 C5 -0.7(7) . . . . no
C2 C1 C13 C12 177.8(5) . . . . no
C13 C1 C2 C3 -0.1(8) . . . . no
C1 C2 C3 C4 1.6(8) . . . . no
C2 C3 C4 C5 -2.2(8) . . . . no
C3 C4 C5 C6 -178.3(5) . . . . no
C3 C4 C5 C13 1.4(7) . . . . no
C6 C5 C13 C1 179.7(5) . . . . no
C4 C5 C6 C7 -2.9(10) . . . . no
C4 C5 C6 C11 177.7(5) . . . . no
C4 C5 C13 C12 -178.7(4) . . . . no
C13 C5 C6 C11 -2.0(6) . . . . no
C4 C5 C13 C1 0.0(8) . . . . no
C6 C5 C13 C12 1.1(6) . . . . no
C13 C5 C6 C7 177.4(5) . . . . no
C11 C6 C7 C8 0.0(8) . . . . no
C5 C6 C11 C10 179.7(5) . . . . no
C5 C6 C7 C8 -179.3(5) . . . . no
C7 C6 C11 C10 0.2(8) . . . . no
C7 C6 C11 C12 -177.4(5) . . . . no
C5 C6 C11 C12 2.1(6) . . . . no
C6 C7 C8 C9 0.1(8) . . . . no
C7 C8 C9 C10 -0.4(8) . . . . no
C8 C9 C10 C11 0.6(8) . . . . no
C9 C10 C11 C6 -0.6(8) . . . . no
C9 C10 C11 C12 176.6(5) . . . . no
C10 C11 C12 C13 -178.8(5) . . . . no
C6 C11 C12 C14 120.3(4) . . . . no
C10 C11 C12 C14 -57.1(7) . . . . no
C6 C11 C12 C13 -1.4(5) . . . . no
C11 C12 C13 C1 -178.4(5) . . . . no
C14 C12 C13 C1 63.1(6) . . . . no
C14 C12 C13 C5 -118.4(5) . . . . no
C11 C12 C13 C5 0.2(5) . . . . no
C13 C12 C14 O1 -66.0(5) . . . . no
C11 C12 C14 O1 179.8(3) . . . . no
C19 C16 C17 N2 -176.4(4) . . . . no
N1 C16 C19 C20 -173.2(4) . . . . no
N1 C16 C17 N2 59.0(5) . . . . no
C17 C16 C19 C20 64.5(5) . . . . no
C17 C16 C19 C21 -172.1(4) . . . . no
N1 C16 C19 C21 -49.8(5) . . . . no
C16 C19 C21 C22 179.3(4) . . . . no
C20 C19 C21 C22 -58.1(6) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 C15 3.689(5) . . no
S1 H1 3.1500 . 1_655 no
S1 H20C 3.1600 . 2_646 no
O1 C1 3.116(6) . . no
O2 C18 3.300(7) . . no
O2 N1 2.892(5) . 1_655 no
O1 H3 2.6500 . 2_555 no
O1 H1 2.6600 . . no
O2 H1N 1.96(6) . 1_655 no
O2 H14A 2.5200 . . no
O2 H14B 2.7300 . . no
O2 H16 2.4000 . . no
O2 H21B 2.8200 . 1_655 no
O2 H4 2.8600 . 2_655 no
N1 O2 2.892(5) . 1_455 no
N1 N2 2.854(6) . . no
N1 C18 3.103(7) . . no
N2 N1 2.854(6) . . no
N2 C15 3.386(7) . . no
N1 H21B 2.4900 . . no
C1 O1 3.116(6) . . no
C9 C20 3.513(8) . 1_554 no
C15 C18 3.197(8) . . no
C15 S1 3.689(5) . . no
C15 N2 3.386(7) . . no
C15 C21 3.559(7) . . no
C17 C22 3.497(8) . 2_546 no
C18 C15 3.197(8) . . no
C18 O2 3.300(7) . . no
C18 N1 3.103(7) . . no
C20 C9 3.513(8) . 1_556 no
C21 C15 3.559(7) . . no
C22 C17 3.497(8) . 2_556 no
C3 H14B 2.8100 . 2_645 no
C4 H21B 2.9100 . 2_545 no
C8 H20B 3.1000 . 1_554 no
C9 H12 2.8400 . 1_655 no
C9 H20B 3.0500 . 1_554 no
C10 H14B 2.8800 . . no
C10 H12 2.8500 . 1_655 no
C14 H10 3.0800 . . no
C15 H21B 3.1000 . . no
C15 H1N 3.08(6) . 1_655 no
C17 H20B 2.6800 . . no
C17 H22C 3.0900 . 2_546 no
C18 H22C 3.0400 . 2_646 no
C18 H17B 3.0000 . 1_655 no
C20 H22C 2.7600 . . no
C20 H17A 2.6700 . . no
C21 H7 3.0900 . 2_655 no
C21 H1N 3.07(6) . . no
C22 H20C 2.7000 . . no
C22 H17B 3.0500 . 2_556 no
H1 S1 3.1500 . 1_455 no
H1 O1 2.6600 . . no
H1 H14A 2.4100 . 1_455 no
H1N O2 1.96(6) . 1_455 no
H1N C15 3.08(6) . 1_455 no
H1N C21 3.07(6) . . no
H1N H21B 2.4900 . . no
H3 O1 2.6500 . 2_545 no
H3 H14B 2.4400 . 2_645 no
H4 O2 2.8600 . 2_645 no
H4 H21B 2.5200 . 2_545 no
H7 C21 3.0900 . 2_645 no
H7 H21A 2.5400 . 2_645 no
H7 H22B 2.5700 . 2_645 no
H8 H20B 2.5500 . 1_654 no
H10 C14 3.0800 . . no
H10 H14B 2.5500 . . no
H12 C9 2.8400 . 1_455 no
H12 C10 2.8500 . 1_455 no
H14A O2 2.5200 . . no
H14A H1 2.4100 . 1_655 no
H14B O2 2.7300 . . no
H14B C10 2.8800 . . no
H14B H10 2.5500 . . no
H14B C3 2.8100 . 2_655 no
H14B H3 2.4400 . 2_655 no
H16 O2 2.4000 . . no
H16 H19 2.2400 . 1_655 no
H16 H20A 2.4900 . . no
H16 H21A 2.5600 . . no
H17A C20 2.6700 . . no
H17A H20B 2.0500 . . no
H17B C18 3.0000 . 1_455 no
H17B H19 2.5300 . . no
H17B C22 3.0500 . 2_546 no
H17B H22C 2.4400 . 2_546 no
H19 H16 2.2400 . 1_455 no
H19 H17B 2.5300 . . no
H19 H22A 2.5500 . . no
H20A H16 2.4900 . . no
H20A H21A 2.5700 . . no
H20B C8 3.1000 . 1_556 no
H20B C9 3.0500 . 1_556 no
H20B C17 2.6800 . . no
H20B H8 2.5500 . 1_456 no
H20B H17A 2.0500 . . no
H20C C22 2.7000 . . no
H20C H22C 2.2400 . . no
H20C S1 3.1600 . 2_656 no
H21A H16 2.5600 . . no
H21A H20A 2.5700 . . no
H21A H22A 2.3500 . 1_655 no
H21A H7 2.5400 . 2_655 no
H21B O2 2.8200 . 1_455 no
H21B N1 2.4900 . . no
H21B C15 3.1000 . . no
H21B H1N 2.4900 . . no
H21B C4 2.9100 . 2_555 no
H21B H4 2.5200 . 2_555 no
H22A H19 2.5500 . . no
H22A H21A 2.3500 . 1_455 no
H22B H7 2.5700 . 2_655 no
H22C C20 2.7600 . . no
H22C H20C 2.2400 . . no
H22C C17 3.0900 . 2_556 no
H22C C18 3.0400 . 2_656 no
H22C H17B 2.4400 . 2_556 no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1N O2 0.99(5) 1.96(6) 2.892(5) 156(5) 1_455 yes
C16 H16 O2 1.0000 2.4000 2.832(6) 105.00 . yes
C21 H21B N1 0.9900 2.4900 2.865(6) 102.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# 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 1030365'
_audit_update_record             
;
2014-11-01 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N2 O2 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C21 H22 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         366.48
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   4.9807(2)
_cell_length_b                   15.9306(6)
_cell_length_c                   12.0456(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.174(4)
_cell_angle_gamma                90
_cell_volume                     943.54(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3702
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      26.0
_cell_special_details            
;
 
;

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.048
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.189
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 18.4

# number of measured reflections (redundant set)
_diffrn_reflns_number            6646
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3702
# number of observed reflections (> n sig(I))
_reflns_number_gt                3223
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     
'W=1/[Σ²(FO²)+(0.0315P)²] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall  - refined all H parameters
# refxyz  - refined H coordinates only
# refU    - refined H U only
# noref   - no refinement of H parameters
# constr  - H parameters constrained
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(6)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration unk

_refine_ls_number_reflns         3702
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S Uani 1.0123(2) 0.19692(6) 0.32734(11) 1.000 0.0541(4) . .
O1 O Uani 0.5883(4) 0.37267(13) 0.13640(17) 1.000 0.0219(7) . .
O2 O Uani 0.9417(4) 0.42094(14) 0.26216(18) 1.000 0.0273(8) . .
N1 N Uani 0.5160(5) 0.40990(17) 0.3066(2) 1.000 0.0236(8) . .
N2 N Uani 0.6957(8) 0.2790(2) 0.4615(3) 1.000 0.0464(14) . .
C1 C Uani 0.4741(7) 0.1799(2) 0.0769(3) 1.000 0.0285(11) . .
C2 C Uani 0.4889(8) 0.0931(2) 0.0953(3) 1.000 0.0356(12) . .
C3 C Uani 0.6387(8) 0.0431(2) 0.0329(3) 1.000 0.0362(11) . .
C4 C Uani 0.7750(8) 0.0767(2) -0.0485(3) 1.000 0.0319(11) . .
C5 C Uani 0.7635(7) 0.16302(19) -0.0652(3) 1.000 0.0235(10) . .
C6 C Uani 0.8858(7) 0.21563(19) -0.1432(3) 1.000 0.0229(10) . .
C7 C Uani 1.0544(7) 0.1959(2) -0.2212(3) 1.000 0.0298(11) . .
C8 C Uani 1.1426(7) 0.2591(3) -0.2851(3) 1.000 0.0320(11) . .
C9 C Uani 1.0649(8) 0.3421(2) -0.2712(3) 1.000 0.0338(11) . .
C10 C Uani 0.8989(7) 0.3626(2) -0.1931(3) 1.000 0.0264(10) . .
C11 C Uani 0.8102(7) 0.2993(2) -0.1292(3) 1.000 0.0228(10) . .
C12 C Uani 0.6359(7) 0.30582(19) -0.0370(3) 1.000 0.0210(10) . .
C13 C Uani 0.6135(7) 0.21403(19) -0.0027(3) 1.000 0.0218(10) . .
C14 C Uani 0.7741(7) 0.3613(2) 0.0572(3) 1.000 0.0227(10) . .
C15 C Uani 0.7011(6) 0.40275(19) 0.2384(3) 1.000 0.0211(10) . .
C16 C Uani 0.5869(7) 0.4266(2) 0.4260(3) 1.000 0.0240(10) . .
C17 C Uani 0.5366(8) 0.3472(2) 0.4910(3) 1.000 0.0365(11) . .
C18 C Uani 0.8274(9) 0.2461(2) 0.4015(4) 1.000 0.0410(14) . .
C19 C Uani 0.4363(7) 0.5036(2) 0.4626(3) 1.000 0.0294(11) . .
C20 C Uani 0.5151(8) 0.5207(2) 0.5884(3) 1.000 0.0375(11) . .
C21 C Uani 0.4990(9) 0.5802(3) 0.3963(3) 1.000 0.0411(14) . .
H1 H Uiso 0.37029 0.21463 0.11822 1.000 0.0339 . .
H1N H Uiso 0.34315 0.40420 0.27784 1.000 0.0283 . .
H2 H Uiso 0.39676 0.06838 0.15038 1.000 0.0426 . .
H3 H Uiso 0.64776 -0.01566 0.04636 1.000 0.0434 . .
H4 H Uiso 0.87361 0.04165 -0.09153 1.000 0.0381 . .
H7 H Uiso 1.10828 0.13947 -0.23031 1.000 0.0357 . .
H8 H Uiso 1.25669 0.24596 -0.33883 1.000 0.0384 . .
H9 H Uiso 1.12640 0.38509 -0.31571 1.000 0.0403 . .
H10 H Uiso 0.84689 0.41921 -0.18358 1.000 0.0317 . .
H12 H Uiso 0.45225 0.32864 -0.06808 1.000 0.0251 . .
H14A H Uiso 0.94414 0.33465 0.09468 1.000 0.0272 . .
H14B H Uiso 0.82018 0.41632 0.02686 1.000 0.0272 . .
H16 H Uiso 0.78620 0.43898 0.44184 1.000 0.0288 . .
H17A H Uiso 0.58288 0.35810 0.57270 1.000 0.0439 . .
H17B H Uiso 0.34152 0.33211 0.47433 1.000 0.0439 . .
H19 H Uiso 0.23621 0.49256 0.44604 1.000 0.0353 . .
H20A H Uiso 0.71308 0.52635 0.60702 1.000 0.0562 . .
H20B H Uiso 0.45438 0.47393 0.63112 1.000 0.0562 . .
H20C H Uiso 0.42835 0.57272 0.60777 1.000 0.0562 . .
H21A H Uiso 0.39968 0.62879 0.41888 1.000 0.0620 . .
H21B H Uiso 0.44312 0.56972 0.31576 1.000 0.0620 . .
H21C H Uiso 0.69480 0.59163 0.41145 1.000 0.0620 . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C18 1.588(4) . . yes
O1 C14 1.443(4) . . yes
O1 C15 1.355(4) . . yes
O2 C15 1.222(4) . . yes
N1 C15 1.334(4) . . yes
N1 C16 1.450(4) . . yes
N2 C17 1.423(5) . . yes
N2 C18 1.174(6) . . yes
N1 H1N 0.8800 . . no
C1 C2 1.401(5) . . no
C1 C13 1.382(5) . . no
C2 C3 1.391(5) . . no
C3 C4 1.386(5) . . no
C4 C5 1.390(4) . . no
C5 C13 1.402(5) . . no
C5 C6 1.462(5) . . no
C6 C11 1.403(4) . . no
C6 C7 1.392(5) . . no
C7 C8 1.381(5) . . no
C8 C9 1.395(6) . . no
C9 C10 1.387(5) . . no
C10 C11 1.383(5) . . no
C11 C12 1.518(5) . . no
C12 C14 1.514(5) . . no
C12 C13 1.528(4) . . no
C16 C17 1.529(5) . . no
C16 C19 1.539(5) . . no
C19 C20 1.528(5) . . no
C19 C21 1.518(6) . . no
C1 H1 0.9500 . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C7 H7 0.9500 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C12 H12 1.0000 . . no
C14 H14A 0.9900 . . no
C14 H14B 0.9900 . . no
C16 H16 1.0000 . . no
C17 H17A 0.9900 . . no
C17 H17B 0.9900 . . no
C19 H19 1.0000 . . no
C20 H20A 0.9800 . . no
C20 H20B 0.9800 . . no
C20 H20C 0.9800 . . no
C21 H21A 0.9800 . . no
C21 H21B 0.9800 . . no
C21 H21C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 C15 115.3(2) . . . yes
C15 N1 C16 122.9(3) . . . yes
C17 N2 C18 152.0(4) . . . yes
C15 N1 H1N 119.00 . . . no
C16 N1 H1N 119.00 . . . no
C2 C1 C13 118.6(3) . . . no
C1 C2 C3 119.9(3) . . . no
C2 C3 C4 121.8(3) . . . no
C3 C4 C5 118.1(3) . . . no
C6 C5 C13 109.0(3) . . . no
C4 C5 C13 120.6(3) . . . no
C4 C5 C6 130.4(3) . . . no
C5 C6 C11 108.7(3) . . . no
C7 C6 C11 119.9(3) . . . no
C5 C6 C7 131.5(3) . . . no
C6 C7 C8 119.4(3) . . . no
C7 C8 C9 120.3(3) . . . no
C8 C9 C10 120.8(3) . . . no
C9 C10 C11 118.9(3) . . . no
C6 C11 C12 110.4(3) . . . no
C10 C11 C12 128.9(3) . . . no
C6 C11 C10 120.7(3) . . . no
C13 C12 C14 113.6(3) . . . no
C11 C12 C13 102.0(3) . . . no
C11 C12 C14 110.1(3) . . . no
C5 C13 C12 110.0(3) . . . no
C1 C13 C12 129.1(3) . . . no
C1 C13 C5 121.0(3) . . . no
O1 C14 C12 107.8(3) . . . yes
O1 C15 O2 123.1(3) . . . yes
O1 C15 N1 111.2(3) . . . yes
O2 C15 N1 125.7(3) . . . yes
N1 C16 C17 108.8(3) . . . yes
C17 C16 C19 112.7(3) . . . no
N1 C16 C19 112.2(3) . . . yes
N2 C17 C16 111.1(3) . . . yes
S1 C18 N2 175.9(4) . . . yes
C20 C19 C21 109.7(3) . . . no
C16 C19 C20 111.5(3) . . . no
C16 C19 C21 109.9(3) . . . no
C2 C1 H1 121.00 . . . no
C13 C1 H1 121.00 . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C3 C4 H4 121.00 . . . no
C5 C4 H4 121.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C7 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C9 C10 H10 121.00 . . . no
C11 C10 H10 120.00 . . . no
C11 C12 H12 110.00 . . . no
C13 C12 H12 110.00 . . . no
C14 C12 H12 110.00 . . . no
O1 C14 H14A 110.00 . . . no
O1 C14 H14B 110.00 . . . no
C12 C14 H14A 110.00 . . . no
C12 C14 H14B 110.00 . . . no
H14A C14 H14B 108.00 . . . no
N1 C16 H16 108.00 . . . no
C17 C16 H16 108.00 . . . no
C19 C16 H16 108.00 . . . no
N2 C17 H17A 109.00 . . . no
N2 C17 H17B 109.00 . . . no
C16 C17 H17A 109.00 . . . no
C16 C17 H17B 109.00 . . . no
H17A C17 H17B 108.00 . . . no
C16 C19 H19 109.00 . . . no
C20 C19 H19 109.00 . . . no
C21 C19 H19 109.00 . . . no
C19 C20 H20A 109.00 . . . no
C19 C20 H20B 109.00 . . . no
C19 C20 H20C 109.00 . . . no
H20A C20 H20B 109.00 . . . no
H20A C20 H20C 109.00 . . . no
H20B C20 H20C 109.00 . . . no
C19 C21 H21A 109.00 . . . no
C19 C21 H21B 110.00 . . . no
C19 C21 H21C 109.00 . . . no
H21A C21 H21B 109.00 . . . no
H21A C21 H21C 109.00 . . . no
H21B C21 H21C 109.00 . . . no

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
C14 O1 C15 N1 -178.9(2) . . . . no
C15 O1 C14 C12 164.3(3) . . . . no
C14 O1 C15 O2 1.5(4) . . . . no
C16 N1 C15 O1 169.1(3) . . . . no
C15 N1 C16 C19 125.9(3) . . . . no
C16 N1 C15 O2 -11.4(5) . . . . no
C15 N1 C16 C17 -108.7(3) . . . . no
C18 N2 C17 C16 -17.8(10) . . . . no
C2 C1 C13 C5 1.0(5) . . . . no
C2 C1 C13 C12 -178.6(3) . . . . no
C13 C1 C2 C3 -0.9(5) . . . . no
C1 C2 C3 C4 -0.3(6) . . . . no
C2 C3 C4 C5 1.3(6) . . . . no
C3 C4 C5 C6 179.7(4) . . . . no
C3 C4 C5 C13 -1.2(5) . . . . no
C6 C5 C13 C1 179.4(3) . . . . no
C4 C5 C6 C7 -2.0(7) . . . . no
C4 C5 C6 C11 178.9(4) . . . . no
C4 C5 C13 C12 179.7(3) . . . . no
C13 C5 C6 C11 -0.3(4) . . . . no
C4 C5 C13 C1 0.1(5) . . . . no
C6 C5 C13 C12 -1.0(4) . . . . no
C13 C5 C6 C7 178.9(4) . . . . no
C11 C6 C7 C8 -0.8(5) . . . . no
C5 C6 C11 C10 180.0(3) . . . . no
C5 C6 C7 C8 -179.9(4) . . . . no
C7 C6 C11 C10 0.8(5) . . . . no
C7 C6 C11 C12 -177.8(3) . . . . no
C5 C6 C11 C12 1.4(4) . . . . no
C6 C7 C8 C9 0.4(5) . . . . no
C7 C8 C9 C10 0.2(6) . . . . no
C8 C9 C10 C11 -0.3(5) . . . . no
C9 C10 C11 C6 -0.2(5) . . . . no
C9 C10 C11 C12 178.1(3) . . . . no
C10 C11 C12 C13 179.7(4) . . . . no
C6 C11 C12 C14 119.0(3) . . . . no
C10 C11 C12 C14 -59.5(5) . . . . no
C6 C11 C12 C13 -1.9(4) . . . . no
C11 C12 C13 C1 -178.7(4) . . . . no
C14 C12 C13 C1 62.9(5) . . . . no
C14 C12 C13 C5 -116.7(3) . . . . no
C11 C12 C13 C5 1.7(4) . . . . no
C13 C12 C14 O1 -72.5(3) . . . . no
C11 C12 C14 O1 174.0(2) . . . . no
C19 C16 C17 N2 -175.3(3) . . . . no
N1 C16 C19 C20 -179.5(3) . . . . no
N1 C16 C17 N2 59.6(4) . . . . no
C17 C16 C19 C20 57.3(4) . . . . no
C17 C16 C19 C21 179.0(3) . . . . no
N1 C16 C19 C21 -57.8(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 C20 3.700(4) . 2_746 no
S1 H17B 3.0900 . 1_655 no
S1 H20A 3.0900 . 2_746 no
S1 H20C 3.1400 . 2_646 no
O1 C1 3.184(4) . . no
O2 N1 2.830(3) . 1_655 no
O2 C18 3.347(4) . . no
O1 H1 2.7400 . . no
O2 H1N 2.0000 . 1_655 no
O2 H14A 2.4400 . . no
O2 H14B 2.8000 . . no
O2 H16 2.4300 . . no
O2 H19 2.7100 . 1_655 no
N1 O2 2.830(3) . 1_455 no
N1 N2 2.846(4) . . no
N1 C18 3.155(5) . . no
N2 N1 2.846(4) . . no
N2 C15 3.337(5) . . no
N1 H21B 2.5800 . . no
N2 H21A 2.8700 . 2_646 no
C1 O1 3.184(4) . . no
C7 C13 3.525(5) . 1_655 no
C9 C17 3.568(5) . 1_554 no
C13 C7 3.525(5) . 1_455 no
C15 N2 3.337(5) . . no
C15 C18 3.176(5) . . no
C17 C9 3.568(5) . 1_556 no
C18 O2 3.347(4) . . no
C18 N1 3.155(5) . . no
C18 C15 3.176(5) . . no
C20 S1 3.700(4) . 2_756 no
C3 H14B 3.0500 . 2_645 no
C8 H12 3.0300 . 1_655 no
C9 H12 2.8700 . 1_655 no
C9 H17A 2.8200 . 1_554 no
C10 H12 2.9700 . 1_655 no
C10 H17A 3.0000 . 1_554 no
C10 H14B 2.8700 . . no
C14 H3 3.0000 . 2_655 no
C17 H20B 2.7000 . . no
C18 H20C 3.0400 . 2_646 no
C18 H17B 2.9100 . 1_655 no
C20 H17A 2.6200 . . no
C21 H8 3.0300 . 2_755 no
H1 O1 2.7400 . . no
H1N O2 2.0000 . 1_455 no
H1N H19 2.5900 . . no
H3 C14 3.0000 . 2_645 no
H3 H12 2.5500 . 2_645 no
H3 H14B 2.5900 . 2_645 no
H4 H14B 2.5600 . 2_745 no
H8 C21 3.0300 . 2_745 no
H9 H20B 2.3300 . 1_654 no
H10 H14B 2.5600 . . no
H12 C8 3.0300 . 1_455 no
H12 C9 2.8700 . 1_455 no
H12 C10 2.9700 . 1_455 no
H12 H3 2.5500 . 2_655 no
H14A O2 2.4400 . . no
H14B O2 2.8000 . . no
H14B C10 2.8700 . . no
H14B H10 2.5600 . . no
H14B C3 3.0500 . 2_655 no
H14B H3 2.5900 . 2_655 no
H14B H4 2.5600 . 2_755 no
H16 O2 2.4300 . . no
H16 H19 2.3900 . 1_655 no
H16 H20A 2.5000 . . no
H16 H21C 2.4900 . . no
H17A C9 2.8200 . 1_556 no
H17A C10 3.0000 . 1_556 no
H17A C20 2.6200 . . no
H17A H20B 2.1100 . . no
H17B S1 3.0900 . 1_455 no
H17B C18 2.9100 . 1_455 no
H19 O2 2.7100 . 1_455 no
H19 H1N 2.5900 . . no
H19 H16 2.3900 . 1_455 no
H20A H16 2.5000 . . no
H20A H21C 2.5600 . . no
H20A S1 3.0900 . 2_756 no
H20B C17 2.7000 . . no
H20B H9 2.3300 . 1_456 no
H20B H17A 2.1100 . . no
H20C H21A 2.4300 . . no
H20C S1 3.1400 . 2_656 no
H20C C18 3.0400 . 2_656 no
H21A H20C 2.4300 . . no
H21A N2 2.8700 . 2_656 no
H21B N1 2.5800 . . no
H21C H16 2.4900 . . no
H21C H20A 2.5600 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1N O2 0.8800 2.0000 2.830(3) 158.00 1_455 yes
C16 H16 O2 1.0000 2.4300 2.853(4) 105.00 . yes
C21 H21B N1 0.9800 2.5800 2.926(5) 101.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# 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_u_mono
_database_code_depnum_ccdc_archive 'CCDC 1030366'
_audit_update_record             
;
2014-11-01 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N2 O2 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C19 H18 N2 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         338.42
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   4.9690(2)
_cell_length_b                   11.3897(4)
_cell_length_c                   15.0388(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.707(3)
_cell_angle_gamma                90
_cell_volume                     850.75(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3343
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      26.0
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.066
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.204
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_T_min  0.85311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'fω scans'
_diffrn_detector_area_resol_mean 8.0419

# number of measured reflections (redundant set)
_diffrn_reflns_number            6544
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.710
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3343
# number of observed reflections (> n sig(I))
_reflns_number_gt                3180
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

#===============================================================================

# 8. REFINEMENT DATA

_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     
'w=1/[σ²(Fo²)+(0.0308P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(4)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3343
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


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
H1N H 0.450(5) 0.590(2) 0.7828(16) 0.018(7) Uiso 1 1 d . . . . .
S1 S 1.02213(15) 0.37620(6) 0.95385(5) 0.0363(2) Uani 1 1 d . . . . .
O1 O 0.7436(3) 0.48625(15) 0.70395(11) 0.0170(4) Uani 1 1 d . . . . .
O2 O 1.0441(3) 0.60697(16) 0.77307(12) 0.0235(4) Uani 1 1 d . . . . .
C6 C 1.1817(5) 0.1780(2) 0.57285(16) 0.0180(5) Uani 1 1 d . . . . .
C16 C 0.6164(5) 0.7040(2) 0.87017(16) 0.0172(5) Uani 1 1 d . . . . .
H16 H 0.8058 0.7263 0.8789 0.021 Uiso 1 1 calc R U . . .
N1 N 0.5997(4) 0.61431(19) 0.80247(14) 0.0176(5) Uani 1 1 d . . . . .
C5 C 1.0543(5) 0.1442(2) 0.65546(16) 0.0181(6) Uani 1 1 d . . . . .
C14 C 0.9565(5) 0.4436(2) 0.64924(17) 0.0180(5) Uani 1 1 d . . . . .
H14A H 1.1204 0.4328 0.6849 0.022 Uiso 1 1 calc R U . . .
H14B H 0.9920 0.4996 0.6024 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8654(5) 0.3276(2) 0.60937(16) 0.0176(5) Uani 1 1 d . . . . .
H12 H 0.6877 0.3359 0.5800 0.021 Uiso 1 1 calc R U . . .
C10 C 1.1519(5) 0.3373(2) 0.46664(17) 0.0234(6) Uani 1 1 d . . . . .
H10 H 1.0766 0.4079 0.4473 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8635(5) 0.2294(2) 0.67652(16) 0.0170(5) Uani 1 1 d . . . . .
C15 C 0.8140(5) 0.5726(2) 0.76128(16) 0.0154(5) Uani 1 1 d . . . . .
C19 C 0.4580(5) 0.8129(2) 0.84326(17) 0.0209(6) Uani 1 1 d . . . . .
H19A H 0.5265 0.8440 0.7891 0.031 Uiso 1 1 calc R U . . .
H19B H 0.4757 0.8708 0.8894 0.031 Uiso 1 1 calc R U . . .
H19C H 0.2715 0.7928 0.8342 0.031 Uiso 1 1 calc R U . . .
N2 N 0.6842(5) 0.5602(2) 0.98891(15) 0.0299(6) Uani 1 1 d . . . . .
C11 C 1.0701(5) 0.2854(2) 0.54380(16) 0.0174(5) Uani 1 1 d . . . . .
C18 C 0.8263(6) 0.4836(3) 0.97069(18) 0.0257(6) Uani 1 1 d . . . . .
C2 C 0.7514(6) 0.1189(2) 0.80504(17) 0.0260(6) Uani 1 1 d . . . . .
H2 H 0.6478 0.1092 0.8550 0.031 Uiso 1 1 calc R U . . .
C8 C 1.4608(5) 0.1771(3) 0.44625(18) 0.0275(6) Uani 1 1 d . . . . .
H8 H 1.5919 0.1414 0.4126 0.033 Uiso 1 1 calc R U . . .
C7 C 1.3795(5) 0.1244(2) 0.52400(17) 0.0243(6) Uani 1 1 d . . . . .
H7 H 1.4565 0.0540 0.5431 0.029 Uiso 1 1 calc R U . . .
C17 C 0.5174(5) 0.6562(2) 0.95743(17) 0.0227(6) Uani 1 1 d . . . . .
H17A H 0.5198 0.7183 1.0016 0.027 Uiso 1 1 calc R U . . .
H17B H 0.3331 0.6293 0.9492 0.027 Uiso 1 1 calc R U . . .
C4 C 1.0975(5) 0.0471(2) 0.71011(18) 0.0238(6) Uani 1 1 d . . . . .
H4 H 1.2263 -0.0088 0.6965 0.029 Uiso 1 1 calc R U . . .
C9 C 1.3484(5) 0.2824(3) 0.41832(17) 0.0272(6) Uani 1 1 d . . . . .
H9 H 1.4059 0.3170 0.3662 0.033 Uiso 1 1 calc R U . . .
C1 C 0.7112(5) 0.2164(2) 0.75143(17) 0.0219(6) Uani 1 1 d . . . . .
H1 H 0.5833 0.2725 0.7655 0.026 Uiso 1 1 calc R U . . .
C3 C 0.9447(5) 0.0354(3) 0.78526(18) 0.0269(6) Uani 1 1 d . . . . .
H3 H 0.9717 -0.0288 0.8227 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C18 1.588(3) . ?
O1 C15 1.348(3) . ?
O1 C14 1.443(3) . ?
O2 C15 1.216(3) . ?
C6 C7 1.387(3) . ?
C6 C11 1.407(3) . ?
C6 C5 1.463(3) . ?
C16 N1 1.443(3) . ?
C16 C17 1.516(3) . ?
C16 C19 1.518(4) . ?
C16 H16 0.9800 . ?
N1 C15 1.335(3) . ?
N1 H1N 0.84(3) . ?
C5 C4 1.391(4) . ?
C5 C13 1.399(3) . ?
C14 C12 1.514(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 C13 1.508(3) . ?
C12 C11 1.516(3) . ?
C12 H12 0.9800 . ?
C10 C11 1.374(3) . ?
C10 C9 1.383(4) . ?
C10 H10 0.9300 . ?
C13 C1 1.384(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 C18 1.160(4) . ?
N2 C17 1.443(3) . ?
C2 C1 1.383(4) . ?
C2 C3 1.391(4) . ?
C2 H2 0.9300 . ?
C8 C9 1.383(4) . ?
C8 C7 1.385(4) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C4 C3 1.387(4) . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C1 H1 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C14 115.45(18) . . ?
C7 C6 C11 119.8(2) . . ?
C7 C6 C5 131.7(2) . . ?
C11 C6 C5 108.4(2) . . ?
N1 C16 C17 110.1(2) . . ?
N1 C16 C19 111.9(2) . . ?
C17 C16 C19 110.2(2) . . ?
N1 C16 H16 108.2 . . ?
C17 C16 H16 108.2 . . ?
C19 C16 H16 108.2 . . ?
C15 N1 C16 123.3(2) . . ?
C15 N1 H1N 115.5(17) . . ?
C16 N1 H1N 120.9(17) . . ?
C4 C5 C13 120.8(2) . . ?
C4 C5 C6 130.4(2) . . ?
C13 C5 C6 108.8(2) . . ?
O1 C14 C12 107.69(19) . . ?
O1 C14 H14A 110.2 . . ?
C12 C14 H14A 110.2 . . ?
O1 C14 H14B 110.2 . . ?
C12 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C13 C12 C14 112.95(19) . . ?
C13 C12 C11 102.6(2) . . ?
C14 C12 C11 109.6(2) . . ?
C13 C12 H12 110.5 . . ?
C14 C12 H12 110.5 . . ?
C11 C12 H12 110.5 . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C1 C13 C5 120.1(2) . . ?
C1 C13 C12 129.7(2) . . ?
C5 C13 C12 110.2(2) . . ?
O2 C15 N1 125.3(2) . . ?
O2 C15 O1 123.6(2) . . ?
N1 C15 O1 111.2(2) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 N2 C17 147.1(3) . . ?
C10 C11 C6 120.8(2) . . ?
C10 C11 C12 129.4(2) . . ?
C6 C11 C12 109.8(2) . . ?
N2 C18 S1 175.5(3) . . ?
C1 C2 C3 120.9(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N2 C17 C16 111.0(2) . . ?
N2 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N2 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C2 C1 C13 119.2(3) . . ?
C2 C1 H1 120.4 . . ?
C13 C1 H1 120.4 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?

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
C17 C16 N1 C15 -118.1(3) . . . . ?
C19 C16 N1 C15 119.1(2) . . . . ?
C7 C6 C5 C4 0.6(4) . . . . ?
C11 C6 C5 C4 -179.1(2) . . . . ?
C7 C6 C5 C13 -179.7(2) . . . . ?
C11 C6 C5 C13 0.7(3) . . . . ?
C15 O1 C14 C12 164.40(19) . . . . ?
O1 C14 C12 C13 -72.1(2) . . . . ?
O1 C14 C12 C11 174.19(19) . . . . ?
C4 C5 C13 C1 -1.4(3) . . . . ?
C6 C5 C13 C1 178.9(2) . . . . ?
C4 C5 C13 C12 177.3(2) . . . . ?
C6 C5 C13 C12 -2.5(3) . . . . ?
C14 C12 C13 C1 63.7(3) . . . . ?
C11 C12 C13 C1 -178.4(2) . . . . ?
C14 C12 C13 C5 -114.9(2) . . . . ?
C11 C12 C13 C5 3.1(2) . . . . ?
C16 N1 C15 O2 -2.6(4) . . . . ?
C16 N1 C15 O1 177.4(2) . . . . ?
C14 O1 C15 O2 -6.2(3) . . . . ?
C14 O1 C15 N1 173.81(19) . . . . ?
C9 C10 C11 C6 -0.6(3) . . . . ?
C9 C10 C11 C12 178.6(2) . . . . ?
C7 C6 C11 C10 1.0(3) . . . . ?
C5 C6 C11 C10 -179.3(2) . . . . ?
C7 C6 C11 C12 -178.4(2) . . . . ?
C5 C6 C11 C12 1.3(3) . . . . ?
C13 C12 C11 C10 178.1(2) . . . . ?
C14 C12 C11 C10 -61.7(3) . . . . ?
C13 C12 C11 C6 -2.6(2) . . . . ?
C14 C12 C11 C6 117.6(2) . . . . ?
C9 C8 C7 C6 0.7(4) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
C5 C6 C7 C8 179.4(2) . . . . ?
C18 N2 C17 C16 -27.3(6) . . . . ?
N1 C16 C17 N2 62.3(3) . . . . ?
C19 C16 C17 N2 -173.9(2) . . . . ?
C13 C5 C4 C3 1.0(3) . . . . ?
C6 C5 C4 C3 -179.3(2) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C11 C10 C9 C8 0.3(4) . . . . ?
C3 C2 C1 C13 0.9(4) . . . . ?
C5 C13 C1 C2 0.4(4) . . . . ?
C12 C13 C1 C2 -178.0(2) . . . . ?
C5 C4 C3 C2 0.3(4) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?


#===END
