# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s_15
_database_code_depnum_ccdc_archive 'CCDC 703635'
_audit_update_record             
;
2008-09-25 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
#TrackingRef '- compound 15.cif.txt'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration 2R,4R
_chemical_formula_sum            'C16 H21 N O5 S'
_chemical_formula_weight         339.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.4240(13)
_cell_length_b                   10.255(2)
_cell_length_c                   27.064(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1782.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       Block
_exptl_crystal_colour            Corlorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1887
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.16
_reflns_number_total             1887
_reflns_number_gt                1317
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'CAD4 software'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PROG (ref, date)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_number_reflns         1887
_refine_ls_number_parameters     207
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.2238
_refine_ls_wR_factor_gt          0.1937
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.8040(5) 0.9732(2) 0.92778(9) 0.0776(8) Uani 1 1 d . . .
N N 0.7426(8) 0.7358(5) 0.89837(19) 0.0377(12) Uani 1 1 d . . .
O1 O 1.0856(12) 1.0277(7) 0.8339(3) 0.107(3) Uani 1 1 d . . .
C1 C 1.2160(19) 1.1279(11) 0.8175(4) 0.107 Uani 1 1 d . . .
H1A H 1.3259 1.1412 0.8410 0.161 Uiso 1 1 calc R . .
H1B H 1.1369 1.2069 0.8141 0.161 Uiso 1 1 calc R . .
H1C H 1.2746 1.1045 0.7861 0.161 Uiso 1 1 calc R . .
O2 O 0.2286(8) 0.6904(7) 0.95256(17) 0.0753(19) Uani 1 1 d . . .
C2 C 0.9198(18) 0.9861(9) 0.8067(4) 0.080(3) Uani 1 1 d U . .
O3 O 0.3510(7) 0.6523(5) 0.87847(16) 0.0552(15) Uani 1 1 d . . .
H3B H 0.2286 0.6350 0.8728 0.083 Uiso 1 1 calc R . .
C3 C 0.868(2) 1.0331(11) 0.7600(4) 0.099(3) Uani 1 1 d U . .
H3A H 0.9505 1.0960 0.7449 0.119 Uiso 1 1 calc R . .
O4 O 0.7318(7) 0.5286(4) 0.91987(16) 0.0446(11) Uani 1 1 d . . .
C4 C 0.700(2) 0.9882(11) 0.7370(4) 0.105(4) Uani 1 1 d U . .
H4A H 0.6648 1.0216 0.7061 0.126 Uiso 1 1 calc R . .
O5 O 0.9603(7) 0.5944(5) 0.86041(16) 0.0431(12) Uani 1 1 d . . .
C5 C 0.5722(18) 0.8899(10) 0.7586(3) 0.086(3) Uani 1 1 d U . .
H5A H 0.4563 0.8577 0.7420 0.104 Uiso 1 1 calc R . .
C6 C 0.6254(13) 0.8438(8) 0.8049(3) 0.0570(19) Uani 1 1 d U . .
H6A H 0.5451 0.7792 0.8196 0.068 Uiso 1 1 calc R . .
C7 C 0.7979(13) 0.8931(7) 0.8296(3) 0.0543(18) Uani 1 1 d U . .
C8 C 0.8534(12) 0.8504(6) 0.8801(2) 0.0462(17) Uani 1 1 d . . .
H8A H 1.0026 0.8305 0.8805 0.055 Uiso 1 1 calc R . .
C9 C 0.5503(14) 0.9067(7) 0.9376(3) 0.059(2) Uani 1 1 d . . .
H9A H 0.4961 0.9336 0.9695 0.070 Uiso 1 1 calc R . .
H9B H 0.4552 0.9357 0.9120 0.070 Uiso 1 1 calc R . .
C10 C 0.5762(10) 0.7603(6) 0.9358(2) 0.0382(15) Uani 1 1 d . . .
H10A H 0.6238 0.7293 0.9681 0.046 Uiso 1 1 calc R . .
C11 C 0.3690(11) 0.6968(7) 0.9236(2) 0.0449(17) Uani 1 1 d . . .
C12 C 0.8227(9) 0.6163(6) 0.8908(2) 0.0342(14) Uani 1 1 d . . .
C13 C 0.7723(12) 0.3876(6) 0.9152(3) 0.0485(18) Uani 1 1 d . . .
C14 C 0.6323(17) 0.3328(8) 0.9547(3) 0.082(3) Uani 1 1 d . . .
H14A H 0.4896 0.3480 0.9459 0.122 Uiso 1 1 calc R . .
H14B H 0.6620 0.3748 0.9857 0.122 Uiso 1 1 calc R . .
H14C H 0.6561 0.2407 0.9578 0.122 Uiso 1 1 calc R . .
C15 C 1.0026(13) 0.3620(8) 0.9268(3) 0.072(2) Uani 1 1 d . . .
H15A H 1.0873 0.3962 0.9006 0.107 Uiso 1 1 calc R . .
H15B H 1.0255 0.2698 0.9297 0.107 Uiso 1 1 calc R . .
H15C H 1.0389 0.4040 0.9573 0.107 Uiso 1 1 calc R . .
C16 C 0.7096(15) 0.3423(8) 0.8653(3) 0.071(2) Uani 1 1 d . . .
H16A H 0.5635 0.3577 0.8606 0.107 Uiso 1 1 calc R . .
H16B H 0.7376 0.2507 0.8622 0.107 Uiso 1 1 calc R . .
H16C H 0.7870 0.3892 0.8407 0.107 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C9 1.786(9) . ?
S C8 1.830(7) . ?
N C12 1.345(8) . ?
N C8 1.460(8) . ?
N C10 1.493(8) . ?
O1 C2 1.364(12) . ?
O1 C1 1.399(12) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O2 C11 1.196(8) . ?
C2 C7 1.382(11) . ?
C2 C3 1.394(14) . ?
O3 C11 1.310(7) . ?
O3 H3B 0.8200 . ?
C3 C4 1.328(15) . ?
C3 H3A 0.9300 . ?
O4 C12 1.331(8) . ?
O4 C13 1.475(8) . ?
C4 C5 1.425(14) . ?
C4 H4A 0.9300 . ?
O5 C12 1.228(7) . ?
C5 C6 1.383(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.390(11) . ?
C6 H6A 0.9300 . ?
C7 C8 1.479(9) . ?
C8 H8A 0.9800 . ?
C9 C10 1.511(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.518(9) . ?
C10 H10A 0.9800 . ?
C13 C16 1.485(10) . ?
C13 C14 1.507(11) . ?
C13 C15 1.535(11) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C9 S C8 90.0(3) . . ?
C12 N C8 119.7(5) . . ?
C12 N C10 122.0(5) . . ?
C8 N C10 116.3(5) . . ?
C2 O1 C1 121.7(9) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 114.5(9) . . ?
O1 C2 C3 124.7(10) . . ?
C7 C2 C3 120.7(11) . . ?
C11 O3 H3B 109.5 . . ?
C4 C3 C2 120.1(11) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C12 O4 C13 122.3(5) . . ?
C3 C4 C5 121.3(10) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C6 C5 C4 118.2(10) . . ?
C6 C5 H5A 120.9 . . ?
C4 C5 H5A 120.9 . . ?
C5 C6 C7 120.7(8) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C2 C7 C6 119.1(8) . . ?
C2 C7 C8 118.9(8) . . ?
C6 C7 C8 122.0(7) . . ?
N C8 C7 115.6(6) . . ?
N C8 S 103.4(4) . . ?
C7 C8 S 113.9(5) . . ?
N C8 H8A 107.8 . . ?
C7 C8 H8A 107.8 . . ?
S C8 H8A 107.8 . . ?
C10 C9 S 105.9(6) . . ?
C10 C9 H9A 110.6 . . ?
S C9 H9A 110.6 . . ?
C10 C9 H9B 110.6 . . ?
S C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
N C10 C9 105.6(6) . . ?
N C10 C11 114.1(5) . . ?
C9 C10 C11 109.7(6) . . ?
N C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
O2 C11 O3 121.6(7) . . ?
O2 C11 C10 122.9(6) . . ?
O3 C11 C10 115.4(6) . . ?
O5 C12 O4 126.0(6) . . ?
O5 C12 N 123.0(6) . . ?
O4 C12 N 111.0(5) . . ?
O4 C13 C16 109.7(6) . . ?
O4 C13 C14 101.5(6) . . ?
C16 C13 C14 111.6(7) . . ?
O4 C13 C15 108.7(6) . . ?
C16 C13 C15 113.2(7) . . ?
C14 C13 C15 111.5(7) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C1 O1 C2 C7 -175.6(8) . . . . ?
C1 O1 C2 C3 2.7(15) . . . . ?
O1 C2 C3 C4 -178.4(10) . . . . ?
C7 C2 C3 C4 -0.2(16) . . . . ?
C2 C3 C4 C5 -1.4(17) . . . . ?
C3 C4 C5 C6 1.2(16) . . . . ?
C4 C5 C6 C7 0.5(13) . . . . ?
O1 C2 C7 C6 -179.7(7) . . . . ?
C3 C2 C7 C6 1.9(13) . . . . ?
O1 C2 C7 C8 1.2(11) . . . . ?
C3 C2 C7 C8 -177.2(8) . . . . ?
C5 C6 C7 C2 -2.0(12) . . . . ?
C5 C6 C7 C8 177.1(8) . . . . ?
C12 N C8 C7 90.5(7) . . . . ?
C10 N C8 C7 -105.3(6) . . . . ?
C12 N C8 S -144.3(5) . . . . ?
C10 N C8 S 20.0(6) . . . . ?
C2 C7 C8 N -169.1(7) . . . . ?
C6 C7 C8 N 11.8(10) . . . . ?
C2 C7 C8 S 71.3(9) . . . . ?
C6 C7 C8 S -107.7(7) . . . . ?
C9 S C8 N -34.4(5) . . . . ?
C9 S C8 C7 91.9(6) . . . . ?
C8 S C9 C10 41.0(5) . . . . ?
C12 N C10 C9 172.7(6) . . . . ?
C8 N C10 C9 8.9(8) . . . . ?
C12 N C10 C11 -66.7(8) . . . . ?
C8 N C10 C11 129.4(6) . . . . ?
S C9 C10 N -34.6(6) . . . . ?
S C9 C10 C11 -158.0(4) . . . . ?
N C10 C11 O2 168.9(7) . . . . ?
C9 C10 C11 O2 -72.9(9) . . . . ?
N C10 C11 O3 -13.0(9) . . . . ?
C9 C10 C11 O3 105.2(7) . . . . ?
C13 O4 C12 O5 -6.7(9) . . . . ?
C13 O4 C12 N 172.8(6) . . . . ?
C8 N C12 O5 -16.2(9) . . . . ?
C10 N C12 O5 -179.6(5) . . . . ?
C8 N C12 O4 164.3(5) . . . . ?
C10 N C12 O4 1.0(8) . . . . ?
C12 O4 C13 C16 -60.8(8) . . . . ?
C12 O4 C13 C14 -178.9(6) . . . . ?
C12 O4 C13 C15 63.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.16
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.069
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s_21
_database_code_depnum_ccdc_archive 'CCDC 703637'
_audit_update_record             
;
2008-09-25 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
#TrackingRef '- compound 21.cif.txt'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration 2R,4R
_chemical_formula_sum            'C15 H18 Cl N O4 S'
_chemical_formula_weight         343.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   6.4600(13)
_cell_length_b                   10.641(2)
_cell_length_c                   12.411(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.52(3)
_cell_angle_gamma                90.00
_cell_volume                     850.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1638
_cell_measurement_theta_min      1.65
_cell_measurement_theta_max      25.26

_exptl_crystal_description       Block
_exptl_crystal_colour            Corlorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.8989
_exptl_absorpt_correction_T_max  0.9646
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1638
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.26
_reflns_number_total             1638
_reflns_number_gt                1363
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'CAD4 software'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PROG (ref, date)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0613P)²+1.3728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(19)
_refine_ls_number_reflns         1638
_refine_ls_number_parameters     185
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.3231(12) 0.3336(8) 0.7816(6) 0.0519(17) Uani 1 1 d U . .
H2 H 0.4185 0.2863 0.7465 0.062 Uiso 1 1 calc R . .
C3 C 0.1505(12) 0.2766(8) 0.8162(7) 0.0555(18) Uani 1 1 d U . .
C4 C 0.0020(13) 0.3440(8) 0.8654(6) 0.0585(18) Uani 1 1 d U . .
H4 H -0.1164 0.3055 0.8879 0.070 Uiso 1 1 calc R . .
C5 C 0.0369(11) 0.4720(7) 0.8800(6) 0.0492(16) Uani 1 1 d U . .
H5 H -0.0603 0.5195 0.9136 0.059 Uiso 1 1 calc R . .
C6 C 0.2109(9) 0.5308(6) 0.8464(5) 0.0350(13) Uani 1 1 d U . .
C1 C 0.3575(11) 0.4607(7) 0.7980(6) 0.0457(16) Uani 1 1 d U . .
H1 H 0.4776 0.4983 0.7767 0.055 Uiso 1 1 calc R . .
C7 C 0.2361(9) 0.6676(6) 0.8692(4) 0.0357(14) Uani 1 1 d U . .
H7 H 0.1036 0.7023 0.8887 0.043 Uiso 1 1 calc R . .
C8 C 0.4826(11) 0.8470(7) 0.9375(5) 0.0497(17) Uani 1 1 d U . .
H8A H 0.3758 0.9042 0.9583 0.060 Uiso 1 1 calc R . .
H8B H 0.6169 0.8773 0.9671 0.060 Uiso 1 1 calc R . .
C9 C 0.4769(9) 0.8350(7) 0.8161(5) 0.0408(14) Uani 1 1 d U . .
H9 H 0.4364 0.9165 0.7843 0.049 Uiso 1 1 calc R . .
O1 O 0.8408(8) 0.8639(5) 0.8108(4) 0.060 Uani 1 1 d . . .
C10 C 0.6910(9) 0.8031(8) 0.7835(5) 0.0459(17) Uani 1 1 d . . .
C11 C 0.2163(9) 0.7473(7) 0.6838(5) 0.0373(14) Uani 1 1 d . . .
C12 C 0.2096(11) 0.8500(8) 0.5098(5) 0.0521(18) Uani 1 1 d . . .
C13 C 0.2564(14) 0.7386(9) 0.4443(8) 0.070 Uani 1 1 d . . .
H13A H 0.3998 0.7161 0.4587 0.106 Uiso 1 1 calc R . .
H13B H 0.2294 0.7580 0.3689 0.106 Uiso 1 1 calc R . .
H13C H 0.1703 0.6696 0.4628 0.106 Uiso 1 1 calc R . .
C14 C -0.0195(13) 0.8804(9) 0.4998(8) 0.069 Uani 1 1 d . . .
H14A H -0.0976 0.8057 0.5120 0.104 Uiso 1 1 calc R . .
H14B H -0.0582 0.9121 0.4287 0.104 Uiso 1 1 calc R . .
H14C H -0.0483 0.9428 0.5525 0.104 Uiso 1 1 calc R . .
C15 C 0.3316(15) 0.9649(9) 0.4750(7) 0.078(3) Uani 1 1 d . . .
H15A H 0.2946 1.0370 0.5158 0.116 Uiso 1 1 calc R . .
H15B H 0.2989 0.9804 0.3994 0.116 Uiso 1 1 calc R . .
H15C H 0.4778 0.9491 0.4881 0.116 Uiso 1 1 calc R . .
Cl1 Cl 0.1155(5) 0.1156(2) 0.7961(2) 0.0909(9) Uani 1 1 d . . .
N1 N 0.3167(7) 0.7456(5) 0.7847(4) 0.0336(11) Uani 1 1 d U . .
O2 O 0.6980(6) 0.7002(6) 0.7256(4) 0.0534(12) Uani 1 1 d . . .
H2A H 0.8184 0.6859 0.7129 0.080 Uiso 1 1 calc R . .
O3 O 0.0721(6) 0.6749(5) 0.6573(3) 0.0398(10) Uani 1 1 d . . .
O4 O 0.2916(7) 0.8324(5) 0.6216(3) 0.0448(11) Uani 1 1 d . . .
S1 S 0.4357(3) 0.68989(18) 0.98363(12) 0.0482(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.368(11) . ?
C2 C1 1.383(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(12) . ?
C3 Cl1 1.743(8) . ?
C4 C5 1.389(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(9) . ?
C5 H5 0.9300 . ?
C6 C1 1.380(9) . ?
C6 C7 1.489(9) . ?
C1 H1 0.9300 . ?
C7 N1 1.464(8) . ?
C7 S1 1.856(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.510(9) . ?
C8 S1 1.801(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.437(8) . ?
C9 C10 1.510(9) . ?
C9 H9 0.9800 . ?
O1 C10 1.191(8) . ?
C10 O2 1.312(9) . ?
C11 O3 1.233(8) . ?
C11 O4 1.308(8) . ?
C11 N1 1.365(8) . ?
C12 O4 1.458(8) . ?
C12 C13 1.483(12) . ?
C12 C14 1.510(11) . ?
C12 C15 1.535(11) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O2 H2A 0.8200 . ?

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
C3 C2 C1 120.9(7) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.4(8) . . ?
C2 C3 Cl1 119.4(7) . . ?
C4 C3 Cl1 119.2(7) . . ?
C3 C4 C5 117.2(8) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 122.2(8) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C1 C6 C5 119.3(6) . . ?
C1 C6 C7 122.9(6) . . ?
C5 C6 C7 117.8(6) . . ?
C6 C1 C2 119.0(7) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
N1 C7 C6 117.2(5) . . ?
N1 C7 S1 102.2(4) . . ?
C6 C7 S1 109.2(4) . . ?
N1 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
S1 C7 H7 109.3 . . ?
C9 C8 S1 104.3(5) . . ?
C9 C8 H8A 110.9 . . ?
S1 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
S1 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
N1 C9 C10 115.7(6) . . ?
N1 C9 C8 106.7(5) . . ?
C10 C9 C8 109.6(5) . . ?
N1 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
O1 C10 O2 123.2(6) . . ?
O1 C10 C9 122.8(7) . . ?
O2 C10 C9 114.0(5) . . ?
O3 C11 O4 125.6(5) . . ?
O3 C11 N1 122.1(6) . . ?
O4 C11 N1 112.3(5) . . ?
O4 C12 C13 110.1(7) . . ?
O4 C12 C14 112.7(6) . . ?
C13 C12 C14 111.5(7) . . ?
O4 C12 C15 102.4(6) . . ?
C13 C12 C15 110.5(6) . . ?
C14 C12 C15 109.2(7) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 N1 C9 121.3(5) . . ?
C11 N1 C7 119.6(5) . . ?
C9 N1 C7 118.1(5) . . ?
C10 O2 H2A 109.5 . . ?
C11 O4 C12 121.8(5) . . ?
C8 S1 C7 90.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 2.0(11) . . . . ?
C1 C2 C3 Cl1 -178.8(6) . . . . ?
C2 C3 C4 C5 -1.1(11) . . . . ?
Cl1 C3 C4 C5 179.8(6) . . . . ?
C3 C4 C5 C6 0.5(11) . . . . ?
C4 C5 C6 C1 -1.0(10) . . . . ?
C4 C5 C6 C7 -178.1(6) . . . . ?
C5 C6 C1 C2 1.9(10) . . . . ?
C7 C6 C1 C2 178.9(6) . . . . ?
C3 C2 C1 C6 -2.4(11) . . . . ?
C1 C6 C7 N1 42.7(8) . . . . ?
C5 C6 C7 N1 -140.2(6) . . . . ?
C1 C6 C7 S1 -72.7(7) . . . . ?
C5 C6 C7 S1 104.3(6) . . . . ?
S1 C8 C9 N1 37.6(6) . . . . ?
S1 C8 C9 C10 -88.4(6) . . . . ?
N1 C9 C10 O1 -174.4(6) . . . . ?
C8 C9 C10 O1 -53.8(9) . . . . ?
N1 C9 C10 O2 3.4(8) . . . . ?
C8 C9 C10 O2 124.0(6) . . . . ?
O3 C11 N1 C9 -176.7(6) . . . . ?
O4 C11 N1 C9 3.6(8) . . . . ?
O3 C11 N1 C7 -8.1(9) . . . . ?
O4 C11 N1 C7 172.2(5) . . . . ?
C10 C9 N1 C11 -83.3(7) . . . . ?
C8 C9 N1 C11 154.5(5) . . . . ?
C10 C9 N1 C7 108.0(6) . . . . ?
C8 C9 N1 C7 -14.3(7) . . . . ?
C6 C7 N1 C11 56.7(7) . . . . ?
S1 C7 N1 C11 176.0(4) . . . . ?
C6 C7 N1 C9 -134.4(6) . . . . ?
S1 C7 N1 C9 -15.1(6) . . . . ?
O3 C11 O4 C12 -0.4(10) . . . . ?
N1 C11 O4 C12 179.3(6) . . . . ?
C13 C12 O4 C11 -67.2(8) . . . . ?
C14 C12 O4 C11 58.1(10) . . . . ?
C15 C12 O4 C11 175.3(6) . . . . ?
C9 C8 S1 C7 -40.7(5) . . . . ?
N1 C7 S1 C8 31.7(4) . . . . ?
C6 C7 S1 C8 156.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.26
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.068
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s_22
_database_code_depnum_ccdc_archive 'CCDC 703638'
_audit_update_record             
;
2008-09-25 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
#TrackingRef '- compound 22.cif.txt'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration 2R,4R
_chemical_formula_sum            'C15 H18 Br N O4 S'
_chemical_formula_weight         388.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   10.485(2)
_cell_length_b                   6.6020(13)
_cell_length_c                   12.803(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.81(3)
_cell_angle_gamma                90.00
_cell_volume                     860.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       Block
_exptl_crystal_colour            Corlorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    2.525
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_T_max  0.7863
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1687
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         25.16
_reflns_number_total             1687
_reflns_number_gt                1281
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'CAD4 software'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PROG (ref, date)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_number_reflns         1687
_refine_ls_number_parameters     203
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1535
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.91931(8) 0.89163(14) 0.76918(8) 0.0595(3) Uani 1 1 d . . .
S S 1.0351(2) 0.3542(6) 0.91245(18) 0.0639(10) Uani 1 1 d . . .
N N 1.2286(5) 0.4003(17) 0.8194(4) 0.0407(15) Uani 1 1 d . . .
O1 O 1.4228(4) 0.393(2) 0.7744(4) 0.0516(13) Uani 1 1 d . . .
C1 C 1.5557(9) 0.6832(18) 0.7473(10) 0.068(3) Uani 1 1 d . . .
H1A H 1.4824 0.7687 0.7161 0.101 Uiso 1 1 calc R . .
H1B H 1.6297 0.7203 0.7195 0.101 Uiso 1 1 calc R . .
H1C H 1.5777 0.6993 0.8240 0.101 Uiso 1 1 calc R . .
O2 O 1.2706(5) 0.6350(10) 0.6998(5) 0.0467(14) Uani 1 1 d . . .
C2 C 1.4756(10) 0.448(3) 0.6021(8) 0.093(6) Uani 1 1 d . . .
H2A H 1.4539 0.3089 0.5836 0.140 Uiso 1 1 calc R . .
H2B H 1.5445 0.4906 0.5693 0.140 Uiso 1 1 calc R . .
H2C H 1.3995 0.5309 0.5766 0.140 Uiso 1 1 calc R . .
C3 C 1.6357(9) 0.3326(17) 0.7705(9) 0.064(3) Uani 1 1 d . . .
H3A H 1.6144 0.1940 0.7511 0.095 Uiso 1 1 calc R . .
H3B H 1.6546 0.3464 0.8473 0.095 Uiso 1 1 calc R . .
H3C H 1.7111 0.3723 0.7452 0.095 Uiso 1 1 calc R . .
O3 O 1.2511(6) 0.0146(12) 0.7647(5) 0.0563(17) Uani 1 1 d U . .
H3D H 1.2571 -0.1074 0.7546 0.084 Uiso 1 1 calc R . .
C4 C 1.5202(9) 0.4668(16) 0.7196(7) 0.055(3) Uani 1 1 d . . .
O4 O 1.3117(8) -0.085(2) 0.9307(6) 0.089(2) Uani 1 1 d U . .
C5 C 1.3072(8) 0.4990(16) 0.7607(7) 0.046(2) Uani 1 1 d . . .
C6 C 1.2819(8) 0.0516(15) 0.8679(7) 0.044(2) Uani 1 1 d U . .
C7 C 1.2758(8) 0.2601(15) 0.9049(7) 0.045(2) Uani 1 1 d . . .
H7A H 1.3666 0.2999 0.9375 0.054 Uiso 1 1 calc R . .
C8 C 1.1991(9) 0.3015(19) 0.9889(7) 0.066(3) Uani 1 1 d . . .
H8A H 1.2352 0.4168 1.0331 0.079 Uiso 1 1 calc R . .
H8B H 1.2002 0.1845 1.0349 0.079 Uiso 1 1 calc R . .
C9 C 1.1017(7) 0.5086(14) 0.8184(6) 0.0392(19) Uani 1 1 d . . .
H9A H 1.1173 0.6486 0.8437 0.047 Uiso 1 1 calc R . .
C10 C 1.0052(8) 0.4988(16) 0.7111(7) 0.046(2) Uani 1 1 d U . .
C11 C 0.9976(8) 0.3382(14) 0.6428(7) 0.051(2) Uani 1 1 d U . .
H11A H 1.0543 0.2297 0.6645 0.062 Uiso 1 1 calc R . .
C12 C 0.9075(10) 0.3270(18) 0.5397(8) 0.063(3) Uani 1 1 d U . .
H12A H 0.9046 0.2154 0.4949 0.075 Uiso 1 1 calc R . .
C13 C 0.8222(10) 0.497(2) 0.5093(8) 0.066(3) Uani 1 1 d U . .
H13A H 0.7633 0.4985 0.4423 0.080 Uiso 1 1 calc R . .
C14 C 0.8259(9) 0.6644(19) 0.5801(8) 0.059(2) Uani 1 1 d U . .
H14A H 0.7696 0.7740 0.5606 0.071 Uiso 1 1 calc R . .
C15 C 0.9166(8) 0.6597(16) 0.6799(7) 0.046(2) Uani 1 1 d 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
Br C15 1.907(10) . ?
S C8 1.797(9) . ?
S C9 1.837(9) . ?
N C5 1.401(12) . ?
N C7 1.429(12) . ?
N C9 1.508(9) . ?
O1 C5 1.374(11) . ?
O1 C4 1.454(11) . ?
C1 C4 1.497(16) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O2 C5 1.191(11) . ?
C2 C4 1.471(13) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.517(14) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
O3 C6 1.306(10) . ?
O3 H3D 0.8200 . ?
O4 C6 1.198(14) . ?
C6 C7 1.462(14) . ?
C7 C8 1.513(12) . ?
C7 H7A 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.501(11) . ?
C9 H9A 0.9800 . ?
C10 C11 1.365(12) . ?
C10 C15 1.404(13) . ?
C11 C12 1.429(12) . ?
C11 H11A 0.9300 . ?
C12 C13 1.431(16) . ?
C12 H12A 0.9300 . ?
C13 C14 1.423(16) . ?
C13 H13A 0.9300 . ?
C14 C15 1.399(13) . ?
C14 H14A 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
C8 S C9 90.0(4) . . ?
C5 N C7 124.9(6) . . ?
C5 N C9 114.0(9) . . ?
C7 N C9 117.2(6) . . ?
C5 O1 C4 117.8(10) . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 O3 H3D 109.5 . . ?
O1 C4 C2 112.1(8) . . ?
O1 C4 C1 111.7(10) . . ?
C2 C4 C1 108.9(11) . . ?
O1 C4 C3 100.2(8) . . ?
C2 C4 C3 114.5(10) . . ?
C1 C4 C3 109.1(8) . . ?
O2 C5 O1 127.2(9) . . ?
O2 C5 N 124.2(8) . . ?
O1 C5 N 108.0(9) . . ?
O4 C6 O3 120.0(10) . . ?
O4 C6 C7 121.0(9) . . ?
O3 C6 C7 119.0(8) . . ?
N C7 C6 113.3(8) . . ?
N C7 C8 106.4(7) . . ?
C6 C7 C8 118.2(8) . . ?
N C7 H7A 106.0 . . ?
C6 C7 H7A 106.0 . . ?
C8 C7 H7A 106.0 . . ?
C7 C8 S 104.4(6) . . ?
C7 C8 H8A 110.9 . . ?
S C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
S C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 N 112.8(6) . . ?
C10 C9 S 107.3(6) . . ?
N C9 S 101.8(6) . . ?
C10 C9 H9A 111.5 . . ?
N C9 H9A 111.5 . . ?
S C9 H9A 111.5 . . ?
C11 C10 C15 118.2(8) . . ?
C11 C10 C9 122.9(9) . . ?
C15 C10 C9 118.9(8) . . ?
C10 C11 C12 123.8(9) . . ?
C10 C11 H11A 118.1 . . ?
C12 C11 H11A 118.1 . . ?
C11 C12 C13 116.3(9) . . ?
C11 C12 H12A 121.9 . . ?
C13 C12 H12A 121.9 . . ?
C14 C13 C12 121.0(9) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C15 C14 C13 118.3(10) . . ?
C15 C14 H14A 120.9 . . ?
C13 C14 H14A 120.9 . . ?
C14 C15 C10 122.4(10) . . ?
C14 C15 Br 116.0(8) . . ?
C10 C15 Br 121.6(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.16
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.087



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_13
_database_code_depnum_ccdc_archive 'CCDC 760948'
_audit_update_record             
;
2010-01-08 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
#TrackingRef '- compound 13.cif.txt'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration 2R,4R
_chemical_formula_sum            'C15 H19 N O4 S'
_chemical_formula_weight         309.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   10.308(2)
_cell_length_b                   6.3790(13)
_cell_length_c                   12.174(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.71(3)
_cell_angle_gamma                90.00
_cell_volume                     786.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       Block
_exptl_crystal_colour            Corlorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1660
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.26
_reflns_number_total             1571
_reflns_number_gt                1348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'CAD4 software'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PROG (ref, date)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+1.4300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         1571
_refine_ls_number_parameters     190
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.47767(13) 0.6336(3) 0.57677(12) 0.0452(4) Uani 1 1 d . . .
N N 0.2771(4) 0.7314(8) 0.6670(4) 0.0313(10) Uani 1 1 d . . .
O1 O 0.1704(7) 0.2140(9) 0.5647(4) 0.0789(19) Uani 1 1 d . . .
C1 C 0.6511(6) 1.0500(16) 0.9019(6) 0.0630(19) Uani 1 1 d U . .
H1A H 0.6954 1.1763 0.9183 0.076 Uiso 1 1 calc R . .
O2 O 0.2738(4) 0.3343(7) 0.7299(3) 0.0493(11) Uani 1 1 d . . .
H2B H 0.2607 0.2148 0.7502 0.074 Uiso 1 1 calc R . .
C2 C 0.6718(6) 0.8942(15) 0.9763(6) 0.0587(18) Uani 1 1 d U . .
H2A H 0.7293 0.9141 1.0440 0.070 Uiso 1 1 calc R . .
O3 O 0.2353(4) 0.9583(7) 0.8009(3) 0.0386(10) Uani 1 1 d . . .
C3 C 0.6070(6) 0.6987(14) 0.9531(5) 0.0537(17) Uani 1 1 d U . .
H3A H 0.6213 0.5899 1.0048 0.064 Uiso 1 1 calc R . .
O4 O 0.0872(3) 0.7097(7) 0.7253(3) 0.0406(10) Uani 1 1 d . . .
C4 C 0.5206(6) 0.6732(12) 0.8502(5) 0.0465(15) Uani 1 1 d U . .
H4A H 0.4782 0.5458 0.8320 0.056 Uiso 1 1 calc R . .
C5 C 0.4988(5) 0.8427(10) 0.7749(4) 0.0347(12) Uani 1 1 d U . .
C6 C 0.5657(6) 1.0276(12) 0.8016(6) 0.0462(15) Uani 1 1 d U . .
H6A H 0.5530 1.1387 0.7513 0.055 Uiso 1 1 calc R . .
C7 C 0.4089(5) 0.8174(10) 0.6646(4) 0.0343(12) Uani 1 1 d . . .
H7A H 0.3985 0.9539 0.6271 0.041 Uiso 1 1 calc R . .
C8 C 0.3157(5) 0.5975(14) 0.4942(4) 0.0489(18) Uani 1 1 d . . .
H8A H 0.2910 0.7156 0.4446 0.059 Uiso 1 1 calc R . .
H8B H 0.3116 0.4703 0.4500 0.059 Uiso 1 1 calc R . .
C9 C 0.2257(5) 0.5817(10) 0.5813(4) 0.0350(13) Uani 1 1 d . . .
H9A H 0.1364 0.6248 0.5461 0.042 Uiso 1 1 calc R . .
C10 C 0.2200(6) 0.3565(11) 0.6238(5) 0.0420(15) Uani 1 1 d . . .
C11 C 0.2009(5) 0.8077(10) 0.7369(5) 0.0345(12) Uani 1 1 d . . .
C12 C -0.0194(5) 0.7779(11) 0.7829(5) 0.0414(15) Uani 1 1 d . . .
C13 C -0.0545(7) 1.0070(13) 0.7534(7) 0.0564(19) Uani 1 1 d . . .
H13A H -0.0845 1.0195 0.6742 0.085 Uiso 1 1 calc R . .
H13B H 0.0221 1.0932 0.7759 0.085 Uiso 1 1 calc R . .
H13C H -0.1232 1.0517 0.7916 0.085 Uiso 1 1 calc R . .
C14 C 0.0242(7) 0.7529(16) 0.9080(5) 0.061(2) Uani 1 1 d . . .
H14A H 0.0455 0.6086 0.9252 0.091 Uiso 1 1 calc R . .
H14B H -0.0459 0.7959 0.9451 0.091 Uiso 1 1 calc R . .
H14C H 0.1006 0.8383 0.9332 0.091 Uiso 1 1 calc R . .
C15 C -0.1309(6) 0.6359(16) 0.7354(6) 0.062(2) Uani 1 1 d . . .
H15A H -0.1068 0.4935 0.7550 0.093 Uiso 1 1 calc R . .
H15B H -0.1497 0.6498 0.6555 0.093 Uiso 1 1 calc R . .
H15C H -0.2077 0.6731 0.7651 0.093 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C8 1.796(6) . ?
S C7 1.818(6) . ?
N C11 1.351(7) . ?
N C9 1.441(7) . ?
N C7 1.470(7) . ?
O1 C10 1.212(8) . ?
C1 C2 1.335(12) . ?
C1 C6 1.373(9) . ?
C1 H1A 0.9300 . ?
O2 C10 1.315(7) . ?
O2 H2B 0.8200 . ?
C2 C3 1.418(12) . ?
C2 H2A 0.9300 . ?
O3 C11 1.246(7) . ?
C3 C4 1.405(8) . ?
C3 H3A 0.9300 . ?
O4 C11 1.312(6) . ?
O4 C12 1.476(6) . ?
C4 C5 1.408(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.375(10) . ?
C5 C7 1.492(7) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9800 . ?
C8 C9 1.537(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.532(9) . ?
C9 H9A 0.9800 . ?
C12 C15 1.492(10) . ?
C12 C14 1.514(8) . ?
C12 C13 1.532(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C8 S C7 89.4(3) . . ?
C11 N C9 121.1(4) . . ?
C11 N C7 121.6(5) . . ?
C9 N C7 116.7(4) . . ?
C2 C1 C6 121.5(8) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
C10 O2 H2B 109.5 . . ?
C1 C2 C3 120.6(6) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 118.5(7) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
C11 O4 C12 122.5(5) . . ?
C3 C4 C5 119.3(7) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 119.5(5) . . ?
C6 C5 C7 120.4(6) . . ?
C4 C5 C7 120.0(6) . . ?
C1 C6 C5 120.6(8) . . ?
C1 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
N C7 C5 116.4(4) . . ?
N C7 S 103.5(4) . . ?
C5 C7 S 110.7(4) . . ?
N C7 H7A 108.6 . . ?
C5 C7 H7A 108.6 . . ?
S C7 H7A 108.6 . . ?
C9 C8 S 103.9(3) . . ?
C9 C8 H8A 111.0 . . ?
S C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
S C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
N C9 C10 114.1(4) . . ?
N C9 C8 105.6(5) . . ?
C10 C9 C8 111.1(5) . . ?
N C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
O1 C10 O2 123.8(6) . . ?
O1 C10 C9 122.7(5) . . ?
O2 C10 C9 113.4(5) . . ?
O3 C11 O4 125.4(5) . . ?
O3 C11 N 122.7(5) . . ?
O4 C11 N 111.8(5) . . ?
O4 C12 C15 103.0(5) . . ?
O4 C12 C14 109.8(5) . . ?
C15 C12 C14 112.9(6) . . ?
O4 C12 C13 109.5(5) . . ?
C15 C12 C13 110.9(6) . . ?
C14 C12 C13 110.5(6) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C6 C1 C2 C3 0.9(11) . . . . ?
C1 C2 C3 C4 -0.1(10) . . . . ?
C2 C3 C4 C5 -1.4(9) . . . . ?
C3 C4 C5 C6 2.2(9) . . . . ?
C3 C4 C5 C7 179.1(5) . . . . ?
C2 C1 C6 C5 -0.1(11) . . . . ?
C4 C5 C6 C1 -1.5(9) . . . . ?
C7 C5 C6 C1 -178.4(6) . . . . ?
C11 N C7 C5 48.7(8) . . . . ?
C9 N C7 C5 -139.3(5) . . . . ?
C11 N C7 S 170.5(4) . . . . ?
C9 N C7 S -17.6(6) . . . . ?
C6 C5 C7 N -131.8(6) . . . . ?
C4 C5 C7 N 51.2(8) . . . . ?
C6 C5 C7 S 110.3(6) . . . . ?
C4 C5 C7 S -66.6(6) . . . . ?
C8 S C7 N 34.6(4) . . . . ?
C8 S C7 C5 160.1(5) . . . . ?
C7 S C8 C9 -42.8(5) . . . . ?
C11 N C9 C10 -79.0(7) . . . . ?
C7 N C9 C10 109.0(6) . . . . ?
C11 N C9 C8 158.7(5) . . . . ?
C7 N C9 C8 -13.3(7) . . . . ?
S C8 C9 N 38.4(6) . . . . ?
S C8 C9 C10 -85.9(6) . . . . ?
N C9 C10 O1 174.3(6) . . . . ?
C8 C9 C10 O1 -66.5(8) . . . . ?
N C9 C10 O2 -5.6(7) . . . . ?
C8 C9 C10 O2 113.7(5) . . . . ?
C12 O4 C11 O3 4.3(9) . . . . ?
C12 O4 C11 N -173.2(5) . . . . ?
C9 N C11 O3 -169.4(5) . . . . ?
C7 N C11 O3 2.2(9) . . . . ?
C9 N C11 O4 8.2(8) . . . . ?
C7 N C11 O4 179.7(5) . . . . ?
C11 O4 C12 C15 174.3(6) . . . . ?
C11 O4 C12 C14 -65.1(8) . . . . ?
C11 O4 C12 C13 56.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.26
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.071
