# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'J Snaith'
_publ_contact_author_email       J.S.SNAITH@BHAM.AC.UK

_publ_section_title              
;
Stereoselective Synthesis of 2,4,5-Trisubstituted
Piperidines by Carbonyl Ene and Prins Cyclisations

;
loop_
_publ_author_name
'J Snaith'
'Claire A. M. Cariou'
'Benson Kariuki'

# Attachment 'Compound9.cif'

data_clc539i
_database_code_depnum_ccdc_archive 'CCDC 689102'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 N O3 S'
_chemical_formula_sum            'C21 H25 N O3 S'
_chemical_formula_weight         371.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.5309(4)
_cell_length_b                   11.6667(6)
_cell_length_c                   20.2195(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.900(4)
_cell_angle_gamma                90.00
_cell_volume                     1976.09(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5722
_cell_measurement_theta_min      4.40
_cell_measurement_theta_max      70.77

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    1.611
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_T_max  0.7388
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12643
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.40
_diffrn_reflns_theta_max         70.77
_reflns_number_total             6257
_reflns_number_gt                5722
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0424P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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   0.029(10)
_refine_ls_number_reflns         6257
_refine_ls_number_parameters     475
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3727(2) -0.03024(18) 0.40037(11) 0.0527(5) Uani 1 1 d . . .
C2 C 0.4663(3) -0.12812(19) 0.41191(12) 0.0607(6) Uani 1 1 d . . .
H2 H 0.5421 -0.1356 0.4513 0.073 Uiso 1 1 calc R . .
C3 C 0.4456(3) -0.2139(2) 0.36438(15) 0.0734(7) Uani 1 1 d . . .
H3 H 0.5082 -0.2796 0.3722 0.088 Uiso 1 1 calc R . .
C4 C 0.3331(3) -0.2052(2) 0.30478(14) 0.0742(7) Uani 1 1 d . . .
C5 C 0.2434(4) -0.1075(2) 0.29433(15) 0.0808(8) Uani 1 1 d . . .
H5 H 0.1693 -0.0995 0.2545 0.097 Uiso 1 1 calc R . .
C6 C 0.2598(3) -0.0205(2) 0.34129(13) 0.0664(6) Uani 1 1 d . . .
H6 H 0.1955 0.0443 0.3335 0.080 Uiso 1 1 calc R . .
C7 C 0.3118(5) -0.3001(3) 0.25259(19) 0.1127(12) Uani 1 1 d . . .
H7A H 0.2024 -0.3247 0.2437 0.169 Uiso 1 1 calc R . .
H7B H 0.3794 -0.3636 0.2693 0.169 Uiso 1 1 calc R . .
H7C H 0.3400 -0.2721 0.2118 0.169 Uiso 1 1 calc R . .
C8 C 0.5822(2) 0.19038(15) 0.38904(9) 0.0399(4) Uani 1 1 d . . .
H8 H 0.6114 0.1224 0.3656 0.048 Uiso 1 1 calc R . .
C9 C 0.7219(2) 0.27444(18) 0.39831(11) 0.0533(5) Uani 1 1 d . . .
H9A H 0.7462 0.2921 0.3545 0.064 Uiso 1 1 calc R . .
H9B H 0.6895 0.3452 0.4171 0.064 Uiso 1 1 calc R . .
C10 C 0.8726(2) 0.23068(19) 0.44368(11) 0.0512(5) Uani 1 1 d . . .
H10 H 0.9541 0.2909 0.4499 0.061 Uiso 1 1 calc R . .
C11 C 0.8321(2) 0.19871(17) 0.51167(10) 0.0455(4) Uani 1 1 d . . .
H11 H 0.7870 0.2668 0.5294 0.055 Uiso 1 1 calc R . .
C12 C 0.7033(2) 0.10745(17) 0.50013(10) 0.0482(4) Uani 1 1 d . . .
H12A H 0.7404 0.0417 0.4781 0.058 Uiso 1 1 calc R . .
H12B H 0.6802 0.0825 0.5430 0.058 Uiso 1 1 calc R . .
C13 C 0.4407(2) 0.24803(15) 0.34422(10) 0.0423(4) Uani 1 1 d . . .
C14 C 0.3637(3) 0.34183(19) 0.36562(11) 0.0549(5) Uani 1 1 d . . .
H14 H 0.3938 0.3681 0.4096 0.066 Uiso 1 1 calc R . .
C15 C 0.2428(3) 0.3964(2) 0.32192(13) 0.0669(6) Uani 1 1 d . . .
H15 H 0.1904 0.4582 0.3370 0.080 Uiso 1 1 calc R . .
C16 C 0.1994(3) 0.3601(2) 0.25656(13) 0.0734(7) Uani 1 1 d . . .
H16 H 0.1175 0.3967 0.2273 0.088 Uiso 1 1 calc R . .
C17 C 0.2772(3) 0.2701(2) 0.23500(13) 0.0767(8) Uani 1 1 d . . .
H17 H 0.2489 0.2461 0.1905 0.092 Uiso 1 1 calc R . .
C18 C 0.3981(3) 0.21330(18) 0.27817(11) 0.0561(5) Uani 1 1 d . . .
H18 H 0.4503 0.1519 0.2625 0.067 Uiso 1 1 calc R . .
C19 C 0.9806(2) 0.1641(2) 0.56215(11) 0.0588(5) Uani 1 1 d . . .
C20 C 1.0239(3) 0.0559(3) 0.57374(16) 0.0900(9) Uani 1 1 d . . .
H20A H 1.1190 0.0386 0.6028 0.108 Uiso 1 1 calc R . .
H20B H 0.9592 -0.0028 0.5528 0.108 Uiso 1 1 calc R . .
C21 C 1.0781(4) 0.2595(4) 0.59382(19) 0.1168(13) Uani 1 1 d . . .
H21A H 1.1624 0.2305 0.6280 0.175 Uiso 1 1 calc R . .
H21B H 1.0127 0.3110 0.6138 0.175 Uiso 1 1 calc R . .
H21C H 1.1231 0.2996 0.5604 0.175 Uiso 1 1 calc R . .
C22 C 0.6452(2) 0.71784(16) 0.09821(10) 0.0449(4) Uani 1 1 d . . .
C23 C 0.7607(3) 0.72143(19) 0.15657(11) 0.0563(5) Uani 1 1 d . . .
H23 H 0.8296 0.7836 0.1654 0.068 Uiso 1 1 calc R . .
C24 C 0.7715(3) 0.6305(2) 0.20146(13) 0.0699(6) Uani 1 1 d . . .
H24 H 0.8483 0.6328 0.2408 0.084 Uiso 1 1 calc R . .
C25 C 0.6718(3) 0.5373(2) 0.18941(13) 0.0675(6) Uani 1 1 d . . .
C26 C 0.5586(3) 0.53503(19) 0.13011(14) 0.0646(6) Uani 1 1 d . . .
H26 H 0.4909 0.4722 0.1210 0.077 Uiso 1 1 calc R . .
C27 C 0.5446(3) 0.62394(17) 0.08454(11) 0.0534(5) Uani 1 1 d . . .
H27 H 0.4685 0.6210 0.0450 0.064 Uiso 1 1 calc R . .
C28 C 0.6817(5) 0.4412(3) 0.24042(18) 0.1065(11) Uani 1 1 d . . .
H28A H 0.7898 0.4336 0.2642 0.160 Uiso 1 1 calc R . .
H28B H 0.6481 0.3707 0.2176 0.160 Uiso 1 1 calc R . .
H28C H 0.6135 0.4583 0.2718 0.160 Uiso 1 1 calc R . .
C29 C 0.45390(19) 0.94357(15) 0.12054(9) 0.0387(4) Uani 1 1 d . . .
H29 H 0.4298 0.8747 0.1445 0.046 Uiso 1 1 calc R . .
C30 C 0.3146(2) 1.02770(17) 0.11666(10) 0.0468(4) Uani 1 1 d . . .
H30A H 0.2985 1.0434 0.1620 0.056 Uiso 1 1 calc R . .
H30B H 0.3434 1.0993 0.0977 0.056 Uiso 1 1 calc R . .
C31 C 0.1577(2) 0.98581(17) 0.07487(10) 0.0460(4) Uani 1 1 d . . .
H31 H 0.0778 1.0470 0.0710 0.055 Uiso 1 1 calc R . .
C32 C 0.1863(2) 0.95360(16) 0.00447(9) 0.0430(4) Uani 1 1 d . . .
H32 H 0.2266 1.0220 -0.0149 0.052 Uiso 1 1 calc R . .
C33 C 0.3156(2) 0.86321(16) 0.01180(9) 0.0437(4) Uani 1 1 d . . .
H33A H 0.2836 0.7971 0.0351 0.052 Uiso 1 1 calc R . .
H33B H 0.3304 0.8387 -0.0324 0.052 Uiso 1 1 calc R . .
C34 C 0.6016(2) 1.00017(16) 0.16141(9) 0.0423(4) Uani 1 1 d . . .
C35 C 0.6621(2) 0.96236(18) 0.22591(10) 0.0486(4) Uani 1 1 d . . .
H35 H 0.6176 0.8985 0.2428 0.058 Uiso 1 1 calc R . .
C36 C 0.7888(3) 1.0190(2) 0.26575(11) 0.0618(6) Uani 1 1 d . . .
H36 H 0.8284 0.9928 0.3091 0.074 Uiso 1 1 calc R . .
C37 C 0.8555(3) 1.1122(2) 0.24205(13) 0.0659(6) Uani 1 1 d . . .
H37 H 0.9405 1.1496 0.2691 0.079 Uiso 1 1 calc R . .
C38 C 0.7972(3) 1.1513(2) 0.17790(12) 0.0638(6) Uani 1 1 d . . .
H38 H 0.8443 1.2142 0.1612 0.077 Uiso 1 1 calc R . .
C39 C 0.6680(2) 1.09698(18) 0.13815(11) 0.0542(5) Uani 1 1 d . . .
H39 H 0.6258 1.1258 0.0956 0.065 Uiso 1 1 calc R . .
C40 C 0.0334(2) 0.9184(2) -0.04171(10) 0.0533(5) Uani 1 1 d . . .
C41 C -0.0074(3) 0.8100(2) -0.05468(13) 0.0722(7) Uani 1 1 d . . .
H41A H -0.1054 0.7925 -0.0816 0.087 Uiso 1 1 calc R . .
H41B H 0.0618 0.7515 -0.0368 0.087 Uiso 1 1 calc R . .
C42 C -0.0749(3) 1.0139(3) -0.06952(16) 0.0867(9) Uani 1 1 d . . .
H42A H -0.1698 0.9831 -0.0969 0.130 Uiso 1 1 calc R . .
H42B H -0.0217 1.0628 -0.0965 0.130 Uiso 1 1 calc R . .
H42C H -0.1029 1.0574 -0.0332 0.130 Uiso 1 1 calc R . .
N1 N 0.55547(16) 0.15463(13) 0.45724(8) 0.0416(3) Uani 1 1 d . . .
N2 N 0.46911(17) 0.90983(13) 0.05038(7) 0.0385(3) Uani 1 1 d . . .
O1 O 0.41671(17) 0.02881(15) 0.52633(8) 0.0640(4) Uani 1 1 d . . .
O2 O 0.25944(15) 0.15519(14) 0.44216(9) 0.0637(4) Uani 1 1 d . . .
O3 O 0.92860(16) 0.13452(17) 0.41257(8) 0.0668(5) Uani 1 1 d . . .
H3A H 1.0241 0.1255 0.4275 0.100 Uiso 1 1 calc R . .
O4 O 0.59496(16) 0.78851(13) -0.02575(7) 0.0542(3) Uani 1 1 d . . .
O5 O 0.76494(15) 0.90447(13) 0.06140(7) 0.0531(3) Uani 1 1 d . . .
O6 O 0.10555(15) 0.89024(15) 0.10820(7) 0.0584(4) Uani 1 1 d . . .
H6A H 0.0127 0.8753 0.0912 0.088 Uiso 1 1 calc R . .
S1 S 0.39251(5) 0.08002(4) 0.46103(3) 0.04873(13) Uani 1 1 d . . .
S2 S 0.62741(5) 0.83372(4) 0.04124(2) 0.04172(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0354(9) 0.0530(11) 0.0676(13) 0.0118(10) 0.0044(9) -0.0084(9)
C2 0.0461(11) 0.0614(12) 0.0747(14) 0.0166(11) 0.0118(11) 0.0014(10)
C3 0.0690(15) 0.0589(13) 0.098(2) 0.0096(14) 0.0304(15) -0.0018(12)
C4 0.0803(17) 0.0643(14) 0.0797(17) 0.0027(13) 0.0192(15) -0.0261(14)
C5 0.0798(17) 0.0721(16) 0.0804(17) 0.0088(14) -0.0104(14) -0.0265(15)
C6 0.0521(12) 0.0582(12) 0.0806(16) 0.0111(12) -0.0085(12) -0.0111(11)
C7 0.156(3) 0.0777(19) 0.108(3) -0.0157(18) 0.035(2) -0.034(2)
C8 0.0297(8) 0.0450(9) 0.0437(9) 0.0022(7) 0.0037(7) 0.0027(7)
C9 0.0370(9) 0.0588(11) 0.0611(12) 0.0147(10) 0.0015(9) -0.0059(9)
C10 0.0319(9) 0.0632(12) 0.0557(11) 0.0042(10) 0.0007(8) -0.0089(9)
C11 0.0303(8) 0.0549(10) 0.0497(10) -0.0045(9) 0.0037(8) 0.0045(8)
C12 0.0304(8) 0.0599(11) 0.0526(11) 0.0132(9) 0.0038(8) 0.0048(8)
C13 0.0339(8) 0.0436(9) 0.0473(10) 0.0029(8) 0.0027(8) -0.0009(8)
C14 0.0552(11) 0.0540(11) 0.0519(11) -0.0028(10) 0.0011(9) 0.0088(10)
C15 0.0661(14) 0.0602(12) 0.0711(15) 0.0029(12) 0.0043(12) 0.0224(12)
C16 0.0658(14) 0.0710(15) 0.0717(15) 0.0083(13) -0.0171(12) 0.0183(13)
C17 0.0859(18) 0.0746(16) 0.0558(13) -0.0096(13) -0.0220(13) 0.0165(15)
C18 0.0575(12) 0.0536(11) 0.0513(11) -0.0072(10) -0.0050(10) 0.0099(10)
C19 0.0329(9) 0.0921(16) 0.0495(11) 0.0018(12) 0.0025(9) 0.0056(11)
C20 0.0563(14) 0.104(2) 0.098(2) 0.0222(18) -0.0148(14) 0.0222(15)
C21 0.0701(19) 0.145(3) 0.112(3) -0.017(3) -0.0413(19) -0.008(2)
C22 0.0358(9) 0.0464(9) 0.0523(11) -0.0051(8) 0.0082(8) 0.0068(8)
C23 0.0471(10) 0.0550(11) 0.0618(13) -0.0023(10) -0.0026(10) 0.0035(9)
C24 0.0710(15) 0.0695(14) 0.0615(14) 0.0073(12) -0.0069(12) 0.0127(13)
C25 0.0755(15) 0.0559(12) 0.0714(15) 0.0086(11) 0.0149(13) 0.0125(12)
C26 0.0616(13) 0.0485(11) 0.0865(17) -0.0029(11) 0.0210(13) -0.0025(11)
C27 0.0484(10) 0.0496(10) 0.0614(12) -0.0076(10) 0.0084(10) 0.0026(9)
C28 0.134(3) 0.0787(18) 0.105(2) 0.0349(18) 0.019(2) 0.013(2)
C29 0.0322(8) 0.0417(8) 0.0408(9) -0.0002(7) 0.0038(7) -0.0037(8)
C30 0.0375(9) 0.0493(9) 0.0523(10) -0.0114(9) 0.0049(8) 0.0015(9)
C31 0.0294(8) 0.0536(10) 0.0528(11) -0.0033(9) 0.0023(8) 0.0049(8)
C32 0.0311(8) 0.0484(9) 0.0481(10) 0.0031(8) 0.0040(8) -0.0016(8)
C33 0.0300(8) 0.0537(10) 0.0452(9) -0.0076(8) 0.0013(8) -0.0029(8)
C34 0.0319(8) 0.0485(10) 0.0448(10) -0.0051(8) 0.0029(8) -0.0012(8)
C35 0.0440(10) 0.0540(10) 0.0457(10) -0.0007(9) 0.0032(9) 0.0028(9)
C36 0.0535(12) 0.0758(14) 0.0479(11) -0.0038(11) -0.0110(10) 0.0080(12)
C37 0.0448(11) 0.0758(15) 0.0703(14) -0.0197(13) -0.0060(11) -0.0083(11)
C38 0.0553(12) 0.0661(13) 0.0680(14) -0.0066(12) 0.0064(11) -0.0201(12)
C39 0.0533(11) 0.0569(11) 0.0489(11) 0.0005(10) 0.0007(9) -0.0113(10)
C40 0.0333(9) 0.0808(13) 0.0440(10) -0.0031(10) 0.0025(8) 0.0004(10)
C41 0.0449(11) 0.0914(18) 0.0731(15) -0.0233(14) -0.0067(11) -0.0098(12)
C42 0.0528(13) 0.112(2) 0.0842(18) 0.0121(18) -0.0165(13) 0.0123(15)
N1 0.0264(7) 0.0495(8) 0.0477(8) 0.0068(7) 0.0035(6) 0.0035(7)
N2 0.0280(7) 0.0454(7) 0.0400(7) -0.0024(6) 0.0013(6) -0.0017(6)
O1 0.0449(7) 0.0840(10) 0.0654(9) 0.0192(8) 0.0160(7) -0.0044(8)
O2 0.0284(6) 0.0724(9) 0.0902(11) 0.0135(9) 0.0112(7) 0.0067(7)
O3 0.0304(6) 0.1114(13) 0.0569(9) -0.0171(9) 0.0044(6) 0.0068(8)
O4 0.0436(7) 0.0722(9) 0.0481(7) -0.0067(7) 0.0120(6) 0.0069(7)
O5 0.0298(6) 0.0627(8) 0.0672(9) -0.0035(7) 0.0101(6) -0.0057(6)
O6 0.0346(6) 0.0855(10) 0.0543(8) 0.0074(8) 0.0066(6) -0.0108(7)
S1 0.02719(19) 0.0583(3) 0.0608(3) 0.0120(2) 0.00867(19) 0.0006(2)
S2 0.02881(19) 0.0505(2) 0.0458(2) -0.0024(2) 0.00697(17) 0.00038(19)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(3) . ?
C1 C6 1.390(3) . ?
C1 S1 1.763(2) . ?
C2 C3 1.376(4) . ?
C3 C4 1.395(4) . ?
C4 C5 1.366(4) . ?
C4 C7 1.517(4) . ?
C5 C6 1.379(4) . ?
C8 N1 1.499(2) . ?
C8 C13 1.522(2) . ?
C8 C9 1.527(3) . ?
C9 C10 1.519(3) . ?
C10 O3 1.413(3) . ?
C10 C11 1.526(3) . ?
C11 C12 1.516(3) . ?
C11 C19 1.524(3) . ?
C12 N1 1.494(2) . ?
C13 C18 1.377(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.370(4) . ?
C16 C17 1.357(4) . ?
C17 C18 1.387(3) . ?
C19 C20 1.324(4) . ?
C19 C21 1.463(4) . ?
C22 C27 1.387(3) . ?
C22 C23 1.387(3) . ?
C22 S2 1.764(2) . ?
C23 C24 1.387(3) . ?
C24 C25 1.374(4) . ?
C25 C26 1.390(4) . ?
C25 C28 1.515(4) . ?
C26 C27 1.378(3) . ?
C29 N2 1.501(2) . ?
C29 C34 1.521(2) . ?
C29 C30 1.532(2) . ?
C30 C31 1.522(2) . ?
C31 O6 1.417(2) . ?
C31 C32 1.536(3) . ?
C32 C40 1.511(3) . ?
C32 C33 1.513(2) . ?
C33 N2 1.494(2) . ?
C34 C35 1.381(3) . ?
C34 C39 1.385(3) . ?
C35 C36 1.387(3) . ?
C36 C37 1.355(4) . ?
C37 C38 1.376(3) . ?
C38 C39 1.388(3) . ?
C40 C41 1.324(4) . ?
C40 C42 1.488(4) . ?
N1 S1 1.6543(15) . ?
N2 S2 1.6555(15) . ?
O1 S1 1.4281(16) . ?
O2 S1 1.4282(15) . ?
O4 S2 1.4310(14) . ?
O5 S2 1.4293(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.7(2) . . ?
C2 C1 S1 120.46(17) . . ?
C6 C1 S1 119.86(17) . . ?
C3 C2 C1 119.2(2) . . ?
C2 C3 C4 121.8(2) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C7 120.8(3) . . ?
C3 C4 C7 121.3(3) . . ?
C4 C5 C6 121.8(3) . . ?
C5 C6 C1 119.7(2) . . ?
N1 C8 C13 115.42(14) . . ?
N1 C8 C9 108.46(15) . . ?
C13 C8 C9 107.57(15) . . ?
C10 C9 C8 114.19(16) . . ?
O3 C10 C9 108.47(18) . . ?
O3 C10 C11 111.12(18) . . ?
C9 C10 C11 108.43(16) . . ?
C12 C11 C19 113.78(18) . . ?
C12 C11 C10 108.31(16) . . ?
C19 C11 C10 111.54(15) . . ?
N1 C12 C11 109.76(15) . . ?
C18 C13 C14 118.75(17) . . ?
C18 C13 C8 118.78(17) . . ?
C14 C13 C8 122.14(18) . . ?
C15 C14 C13 120.3(2) . . ?
C16 C15 C14 120.5(2) . . ?
C17 C16 C15 119.3(2) . . ?
C16 C17 C18 121.2(2) . . ?
C13 C18 C17 119.9(2) . . ?
C20 C19 C21 122.1(2) . . ?
C20 C19 C11 122.7(2) . . ?
C21 C19 C11 115.0(2) . . ?
C27 C22 C23 120.43(19) . . ?
C27 C22 S2 120.10(15) . . ?
C23 C22 S2 119.47(15) . . ?
C22 C23 C24 118.8(2) . . ?
C25 C24 C23 121.8(2) . . ?
C24 C25 C26 118.3(2) . . ?
C24 C25 C28 120.8(3) . . ?
C26 C25 C28 120.9(3) . . ?
C27 C26 C25 121.4(2) . . ?
C26 C27 C22 119.3(2) . . ?
N2 C29 C34 114.61(14) . . ?
N2 C29 C30 108.93(14) . . ?
C34 C29 C30 107.75(14) . . ?
C31 C30 C29 114.52(15) . . ?
O6 C31 C30 108.10(16) . . ?
O6 C31 C32 111.55(16) . . ?
C30 C31 C32 108.42(15) . . ?
C40 C32 C33 113.53(16) . . ?
C40 C32 C31 111.70(15) . . ?
C33 C32 C31 108.69(15) . . ?
N2 C33 C32 110.38(14) . . ?
C35 C34 C39 118.50(18) . . ?
C35 C34 C29 119.85(17) . . ?
C39 C34 C29 121.31(17) . . ?
C34 C35 C36 120.5(2) . . ?
C37 C36 C35 120.7(2) . . ?
C36 C37 C38 119.9(2) . . ?
C37 C38 C39 120.0(2) . . ?
C34 C39 C38 120.4(2) . . ?
C41 C40 C42 121.3(2) . . ?
C41 C40 C32 123.1(2) . . ?
C42 C40 C32 115.6(2) . . ?
C12 N1 C8 112.21(13) . . ?
C12 N1 S1 113.82(12) . . ?
C8 N1 S1 117.67(12) . . ?
C33 N2 C29 111.41(13) . . ?
C33 N2 S2 113.53(11) . . ?
C29 N2 S2 117.66(11) . . ?
O1 S1 O2 118.20(10) . . ?
O1 S1 N1 106.69(8) . . ?
O2 S1 N1 107.28(8) . . ?
O1 S1 C1 108.42(11) . . ?
O2 S1 C1 107.18(10) . . ?
N1 S1 C1 108.81(9) . . ?
O5 S2 O4 118.96(9) . . ?
O5 S2 N2 107.54(8) . . ?
O4 S2 N2 106.71(7) . . ?
O5 S2 C22 106.96(9) . . ?
O4 S2 C22 108.24(9) . . ?
N2 S2 C22 108.04(8) . . ?

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        70.77
_diffrn_measured_fraction_theta_full 0.930
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.039

# Attachment 'Compound11g.cif'

data_clc439c
_database_code_depnum_ccdc_archive 'CCDC 689103'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 Cl N O5 S'
_chemical_formula_sum            'C16 H21 Cl N O5 S'
_chemical_formula_weight         374.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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/n

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

_cell_length_a                   9.7846(5)
_cell_length_b                   20.8046(11)
_cell_length_c                   9.7963(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.656(4)
_cell_angle_gamma                90.00
_cell_volume                     1877.98(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2976
_cell_measurement_theta_min      4.25
_cell_measurement_theta_max      70.78

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    3.058
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5273
_exptl_absorpt_correction_T_max  0.6091
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12036
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.25
_diffrn_reflns_theta_max         70.78
_reflns_number_total             3314
_reflns_number_gt                2976
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1437P)^2^+0.8334P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3314
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1955
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8247(3) 0.19258(11) 0.5576(3) 0.0391(5) Uani 1 1 d . . .
H1 H 0.8635 0.1571 0.6254 0.047 Uiso 1 1 calc R . .
C2 C 0.9508(3) 0.23782(13) 0.5674(3) 0.0427(6) Uani 1 1 d . . .
H2A H 1.0168 0.2169 0.5264 0.051 Uiso 1 1 calc R . .
H2B H 1.0039 0.2473 0.6683 0.051 Uiso 1 1 calc R . .
C3 C 0.8961(3) 0.30048(12) 0.4860(3) 0.0415(6) Uani 1 1 d . . .
H3 H 0.9785 0.3292 0.4975 0.050 Uiso 1 1 calc R . .
C4 C 0.7884(2) 0.33323(11) 0.5464(3) 0.0372(5) Uani 1 1 d . . .
H4 H 0.8390 0.3390 0.6506 0.045 Uiso 1 1 calc R . .
C5 C 0.6619(3) 0.28743(12) 0.5314(3) 0.0385(5) Uani 1 1 d . . .
H5A H 0.5949 0.3067 0.5733 0.046 Uiso 1 1 calc R . .
H5B H 0.6099 0.2789 0.4298 0.046 Uiso 1 1 calc R . .
C6 C 0.7530(3) 0.16341(11) 0.4078(3) 0.0404(6) Uani 1 1 d . . .
C7 C 0.8020(4) 0.1157(2) 0.2111(4) 0.0815(12) Uani 1 1 d . . .
H7A H 0.7308 0.0829 0.2041 0.122 Uiso 1 1 calc R . .
H7B H 0.8815 0.0976 0.1874 0.122 Uiso 1 1 calc R . .
H7C H 0.7588 0.1498 0.1446 0.122 Uiso 1 1 calc R . .
C8 C 0.7377(3) 0.40056(13) 0.4840(3) 0.0447(6) Uani 1 1 d . . .
C9 C 0.6314(4) 0.40236(16) 0.3279(4) 0.0659(9) Uani 1 1 d . . .
H9A H 0.6744 0.3814 0.2649 0.099 Uiso 1 1 calc R . .
H9B H 0.6099 0.4462 0.2980 0.099 Uiso 1 1 calc R . .
H9C H 0.5435 0.3805 0.3231 0.099 Uiso 1 1 calc R . .
C11 C 0.5241(3) 0.14060(12) 0.6441(3) 0.0405(6) Uani 1 1 d . . .
C12 C 0.5411(3) 0.07650(13) 0.6827(3) 0.0506(6) Uani 1 1 d . . .
H12 H 0.6272 0.0620 0.7504 0.061 Uiso 1 1 calc R . .
C13 C 0.4283(4) 0.03406(14) 0.6190(4) 0.0588(8) Uani 1 1 d . . .
H13 H 0.4398 -0.0092 0.6442 0.071 Uiso 1 1 calc R . .
C14 C 0.2998(3) 0.05462(14) 0.5195(3) 0.0527(7) Uani 1 1 d . . .
C15 C 0.2854(3) 0.11904(14) 0.4809(3) 0.0502(6) Uani 1 1 d . . .
H15 H 0.1996 0.1335 0.4126 0.060 Uiso 1 1 calc R . .
C16 C 0.3967(3) 0.16220(13) 0.5425(3) 0.0473(6) Uani 1 1 d . . .
H16 H 0.3860 0.2053 0.5157 0.057 Uiso 1 1 calc R . .
C17 C 0.1757(4) 0.00811(19) 0.4522(5) 0.0778(10) Uani 1 1 d . . .
H17A H 0.1931 -0.0149 0.3747 0.117 Uiso 1 1 calc R . .
H17B H 0.0864 0.0316 0.4149 0.117 Uiso 1 1 calc R . .
H17C H 0.1693 -0.0217 0.5245 0.117 Uiso 1 1 calc R . .
N1 N 0.7201(2) 0.22717(10) 0.6071(2) 0.0416(5) Uani 1 1 d . . .
O1 O 0.8250(2) 0.28779(10) 0.3362(2) 0.0514(5) Uani 1 1 d . . .
H1W H 0.8843 0.2746 0.3004 0.077 Uiso 1 1 calc R . .
O2 O 0.6251(2) 0.15881(10) 0.3460(2) 0.0556(5) Uani 1 1 d . . .
O3 O 0.8539(2) 0.14044(10) 0.3556(2) 0.0544(5) Uani 1 1 d . . .
O4 O 0.7785(2) 0.16151(13) 0.8289(2) 0.0675(7) Uani 1 1 d . . .
O5 O 0.5949(2) 0.24769(11) 0.7808(2) 0.0610(6) Uani 1 1 d . . .
S1 S 0.66203(7) 0.19624(3) 0.72884(6) 0.0441(3) Uani 1 1 d . . .
Cl1 Cl 0.65505(14) 0.43803(5) 0.60283(13) 0.0609(4) Uani 0.643(3) 1 d P . .
Cl1A Cl 0.8801(2) 0.44893(10) 0.5004(3) 0.0638(8) Uani 0.357(3) 1 d P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0398(13) 0.0420(13) 0.0374(13) 0.0053(9) 0.0156(10) 0.0043(10)
C2 0.0312(12) 0.0525(14) 0.0428(13) -0.0037(10) 0.0102(10) 0.0001(10)
C3 0.0356(12) 0.0486(14) 0.0436(14) -0.0017(10) 0.0176(10) -0.0085(9)
C4 0.0372(12) 0.0403(13) 0.0350(12) -0.0007(9) 0.0134(9) -0.0034(9)
C5 0.0366(12) 0.0403(12) 0.0438(13) 0.0017(10) 0.0202(10) -0.0003(9)
C6 0.0390(13) 0.0376(12) 0.0454(13) 0.0025(9) 0.0151(10) 0.0010(9)
C7 0.078(2) 0.102(3) 0.063(2) -0.033(2) 0.0215(18) 0.011(2)
C8 0.0490(14) 0.0403(13) 0.0445(14) 0.0004(10) 0.0153(11) -0.0063(11)
C9 0.066(2) 0.0511(16) 0.0601(19) 0.0079(13) -0.0059(15) -0.0006(14)
C11 0.0442(13) 0.0446(13) 0.0381(12) 0.0030(9) 0.0209(10) -0.0038(10)
C12 0.0536(16) 0.0454(14) 0.0542(16) 0.0111(11) 0.0198(13) 0.0012(12)
C13 0.0710(19) 0.0435(15) 0.0656(18) 0.0097(12) 0.0279(15) -0.0045(13)
C14 0.0587(16) 0.0531(16) 0.0535(16) -0.0024(12) 0.0284(13) -0.0129(13)
C15 0.0465(15) 0.0550(16) 0.0482(14) -0.0002(11) 0.0148(12) -0.0031(12)
C16 0.0546(15) 0.0406(13) 0.0477(15) 0.0031(10) 0.0185(12) -0.0006(11)
C17 0.079(2) 0.071(2) 0.087(2) -0.0025(19) 0.032(2) -0.0334(19)
N1 0.0444(11) 0.0427(11) 0.0456(12) 0.0048(8) 0.0254(9) 0.0004(9)
O1 0.0594(12) 0.0620(12) 0.0406(10) 0.0030(8) 0.0270(9) 0.0040(9)
O2 0.0428(11) 0.0644(13) 0.0555(12) -0.0082(9) 0.0112(9) -0.0045(9)
O3 0.0510(11) 0.0612(12) 0.0524(11) -0.0131(9) 0.0192(9) 0.0070(9)
O4 0.0566(12) 0.0951(17) 0.0444(11) 0.0209(10) 0.0085(9) -0.0128(11)
O5 0.0754(14) 0.0659(13) 0.0590(12) -0.0209(10) 0.0453(11) -0.0239(11)
S1 0.0478(4) 0.0536(4) 0.0349(4) 0.0005(2) 0.0192(3) -0.0111(2)
Cl1 0.0774(8) 0.0433(6) 0.0724(8) -0.0028(5) 0.0388(6) 0.0137(5)
Cl1A 0.0554(12) 0.0481(11) 0.0831(15) 0.0106(9) 0.0171(10) -0.0105(8)

_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 N1 1.462(3) . ?
C1 C6 1.524(4) . ?
C1 C2 1.529(3) . ?
C2 C3 1.528(4) . ?
C3 O1 1.421(3) . ?
C3 C4 1.531(3) . ?
C4 C5 1.529(3) . ?
C4 C8 1.542(3) . ?
C5 N1 1.470(3) . ?
C6 O2 1.197(3) . ?
C6 O3 1.343(3) . ?
C7 O3 1.430(4) . ?
C8 C9 1.533(4) . ?
C8 Cl1A 1.681(3) . ?
C8 Cl1 1.803(3) . ?
C11 C12 1.381(4) . ?
C11 C16 1.382(4) . ?
C11 S1 1.760(3) . ?
C12 C13 1.387(4) . ?
C13 C14 1.375(5) . ?
C14 C15 1.387(4) . ?
C14 C17 1.519(4) . ?
C15 C16 1.384(4) . ?
N1 S1 1.617(2) . ?
O4 S1 1.425(2) . ?
O5 S1 1.436(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 111.7(2) . . ?
N1 C1 C2 108.5(2) . . ?
C6 C1 C2 114.0(2) . . ?
C1 C2 C3 111.02(19) . . ?
O1 C3 C2 110.1(2) . . ?
O1 C3 C4 108.7(2) . . ?
C2 C3 C4 110.1(2) . . ?
C5 C4 C3 108.98(19) . . ?
C5 C4 C8 112.7(2) . . ?
C3 C4 C8 115.0(2) . . ?
N1 C5 C4 108.63(19) . . ?
O2 C6 O3 123.9(2) . . ?
O2 C6 C1 125.6(2) . . ?
O3 C6 C1 110.4(2) . . ?
C9 C8 C4 116.0(2) . . ?
C9 C8 Cl1A 110.1(2) . . ?
C4 C8 Cl1A 111.11(19) . . ?
C9 C8 Cl1 109.4(2) . . ?
C4 C8 Cl1 106.90(17) . . ?
Cl1A C8 Cl1 102.49(16) . . ?
C12 C11 C16 120.5(2) . . ?
C12 C11 S1 120.2(2) . . ?
C16 C11 S1 119.2(2) . . ?
C11 C12 C13 119.1(3) . . ?
C14 C13 C12 121.4(3) . . ?
C13 C14 C15 118.6(3) . . ?
C13 C14 C17 121.1(3) . . ?
C15 C14 C17 120.3(3) . . ?
C16 C15 C14 121.0(3) . . ?
C11 C16 C15 119.3(3) . . ?
C1 N1 C5 116.60(19) . . ?
C1 N1 S1 120.54(17) . . ?
C5 N1 S1 122.62(16) . . ?
C6 O3 C7 116.3(2) . . ?
O4 S1 O5 119.34(15) . . ?
O4 S1 N1 108.11(12) . . ?
O5 S1 N1 106.31(12) . . ?
O4 S1 C11 107.47(14) . . ?
O5 S1 C11 106.71(12) . . ?
N1 S1 C11 108.54(12) . . ?

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        70.78
_diffrn_measured_fraction_theta_full 0.923
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.095

# Attachment 'Compound_15.cif'

data_clc445b
_database_code_depnum_ccdc_archive 'CCDC 689104'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N O4 S'
_chemical_formula_sum            'C16 H19 N O4 S'
_chemical_formula_weight         321.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6519(2)
_cell_length_b                   11.7291(2)
_cell_length_c                   14.7538(3)
_cell_angle_alpha                74.5980(10)
_cell_angle_beta                 82.5680(10)
_cell_angle_gamma                64.3790(10)
_cell_volume                     1602.14(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3916
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      70.66

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    1.950
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5923
_exptl_absorpt_correction_T_max  0.8596
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10385
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         70.66
_reflns_number_total             5338
_reflns_number_gt                3916
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

The asymmetric unit consists of two independent molecules with a segment of
one of the molecules being disordered. The geometry of the two disorder
components has been restrained to be similar to that in the other
molecule during refinement.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+0.5910P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5338
_refine_ls_number_parameters     419
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1589
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8843(3) 0.7567(2) 0.4692(2) 0.0436(6) Uani 1 1 d . A 1
C2 C 0.9329(4) 0.7368(3) 0.3815(3) 0.0722(10) Uani 1 1 d . A 1
H2 H 0.8747 0.7801 0.3299 0.087 Uiso 1 1 calc R A 1
C3 C 1.0708(4) 0.6509(4) 0.3707(3) 0.0773(11) Uani 1 1 d . A 1
H3 H 1.1055 0.6396 0.3110 0.093 Uiso 1 1 calc R A 1
C4 C 1.1564(3) 0.5824(3) 0.4471(3) 0.0566(8) Uani 1 1 d . A 1
C5 C 1.1057(3) 0.6056(3) 0.5334(3) 0.0654(9) Uani 1 1 d . A 1
H5 H 1.1634 0.5615 0.5851 0.079 Uiso 1 1 calc R A 1
C6 C 0.9702(3) 0.6933(3) 0.5456(2) 0.0597(8) Uani 1 1 d . A 1
H6 H 0.9379 0.7092 0.6046 0.072 Uiso 1 1 calc R A 1
C7 C 1.3045(4) 0.4864(3) 0.4343(3) 0.0834(12) Uani 1 1 d . A 1
H7A H 1.3636 0.5318 0.4160 0.125 Uiso 1 1 calc R A 1
H7B H 1.3077 0.4436 0.3863 0.125 Uiso 1 1 calc R A 1
H7C H 1.3362 0.4230 0.4924 0.125 Uiso 1 1 calc R A 1
C8 C 0.6513(3) 1.0704(3) 0.3344(2) 0.0489(7) Uani 1 1 d . A 1
H8A H 0.5838 1.0424 0.3207 0.059 Uiso 1 1 calc R A 1
H8B H 0.7317 1.0416 0.2932 0.059 Uiso 1 1 calc R A 1
C9 C 0.5872(3) 1.2190(3) 0.3163(2) 0.0519(7) Uani 1 1 d . A 1
H9 H 0.4962 1.2444 0.3486 0.062 Uiso 1 1 calc R A 1
C10 C 0.6743(3) 1.2623(3) 0.3626(2) 0.0561(8) Uani 1 1 d . A 1
H10 H 0.6402 1.3572 0.3471 0.067 Uiso 1 1 calc R A 1
C11 C 0.6789(3) 1.2073(3) 0.4682(2) 0.0528(7) Uani 1 1 d . A 1
H11A H 0.7201 1.2447 0.5003 0.063 Uiso 1 1 calc R A 1
H11B H 0.5875 1.2183 0.4952 0.063 Uiso 1 1 calc R A 1
C12 C 0.7725(3) 1.0664(3) 0.4689(2) 0.0454(6) Uani 1 1 d . A 1
H12 H 0.8131 1.0153 0.5305 0.055 Uiso 1 1 calc R A 1
C13 C 0.5593(4) 1.2822(3) 0.2125(3) 0.0775(11) Uani 0.547(9) 1 d PD A 1
C14 C 0.4473(13) 1.2777(14) 0.1785(7) 0.180(8) Uani 0.547(9) 1 d PD A 1
H14A H 0.4068 1.3343 0.1224 0.216 Uiso 0.547(9) 1 calc PR A 1
H14B H 0.4122 1.2181 0.2117 0.216 Uiso 0.547(9) 1 calc PR A 1
C15 C 0.6168(16) 1.3700(14) 0.1656(7) 0.152(7) Uani 0.547(9) 1 d PD A 1
H15A H 0.6930 1.3578 0.2011 0.228 Uiso 0.547(9) 1 calc PR A 1
H15B H 0.5469 1.4575 0.1594 0.228 Uiso 0.547(9) 1 calc PR A 1
H15C H 0.6499 1.3549 0.1044 0.228 Uiso 0.547(9) 1 calc PR A 1
C13A C 0.5593(4) 1.2822(3) 0.2125(3) 0.0775(11) Uani 0.453(9) 1 d PD A 2
C14A C 0.4734(17) 1.4131(8) 0.1839(8) 0.142(7) Uani 0.453(9) 1 d PD A 2
H14C H 0.4726 1.4561 0.1210 0.171 Uiso 0.453(9) 1 calc PR A 2
H14D H 0.4165 1.4582 0.2276 0.171 Uiso 0.453(9) 1 calc PR A 2
C15A C 0.6442(14) 1.2194(10) 0.1406(6) 0.127(6) Uani 0.453(9) 1 d PD A 2
H15D H 0.6615 1.1290 0.1576 0.190 Uiso 0.453(9) 1 calc PR A 2
H15E H 0.7311 1.2272 0.1344 0.190 Uiso 0.453(9) 1 calc PR A 2
H15F H 0.5966 1.2600 0.0818 0.190 Uiso 0.453(9) 1 calc PR A 2
C16 C 0.8810(3) 1.0830(4) 0.3943(2) 0.0584(8) Uani 1 1 d . A 1
C17 C 0.7950(3) 0.6536(3) 0.1052(2) 0.0593(8) Uani 1 1 d . B 1
C18 C 0.8920(4) 0.6074(4) 0.1733(3) 0.0882(13) Uani 1 1 d . B 1
H18 H 0.8967 0.6638 0.2054 0.106 Uiso 1 1 calc R B 1
C19 C 0.9819(5) 0.4790(5) 0.1947(4) 0.1123(18) Uani 1 1 d . B 1
H19 H 1.0480 0.4496 0.2407 0.135 Uiso 1 1 calc R B 1
C20 C 0.9773(6) 0.3932(4) 0.1505(4) 0.1064(19) Uani 1 1 d . B 1
C21 C 0.8827(7) 0.4397(5) 0.0807(5) 0.126(2) Uani 1 1 d . B 1
H21 H 0.8795 0.3825 0.0488 0.151 Uiso 1 1 calc R B 1
C22 C 0.7892(6) 0.5731(4) 0.0558(3) 0.1001(15) Uani 1 1 d . B 1
H22 H 0.7263 0.6044 0.0074 0.120 Uiso 1 1 calc R B 1
C23 C 1.0759(6) 0.2500(4) 0.1737(5) 0.173(3) Uani 1 1 d . B 1
H23A H 1.0510 0.2049 0.1386 0.260 Uiso 1 1 calc R B 1
H23B H 1.0696 0.2139 0.2398 0.260 Uiso 1 1 calc R B 1
H23C H 1.1696 0.2405 0.1575 0.260 Uiso 1 1 calc R B 1
C24 C 0.4320(3) 0.8099(3) 0.1041(2) 0.0577(8) Uani 1 1 d . B 1
H24A H 0.4581 0.7169 0.1225 0.069 Uiso 1 1 calc R B 1
H24B H 0.4294 0.8363 0.0360 0.069 Uiso 1 1 calc R B 1
C25 C 0.2883(3) 0.8806(3) 0.1447(2) 0.0571(8) Uani 1 1 d . B 1
H25 H 0.2579 0.9729 0.1131 0.068 Uiso 1 1 calc R B 1
C26 C 0.2998(3) 0.8710(3) 0.2491(2) 0.0566(8) Uani 1 1 d . B 1
H26 H 0.2079 0.9100 0.2782 0.068 Uiso 1 1 calc R B 1
C27 C 0.3942(3) 0.9327(3) 0.2618(2) 0.0577(8) Uani 1 1 d . B 1
H27A H 0.3734 1.0163 0.2180 0.069 Uiso 1 1 calc R B 1
H27B H 0.3907 0.9418 0.3257 0.069 Uiso 1 1 calc R B 1
C28 C 0.5313(3) 0.8291(3) 0.2388(2) 0.0520(7) Uani 1 1 d . B 1
H28 H 0.6116 0.8341 0.2602 0.062 Uiso 1 1 calc R B 1
C29 C 0.1775(4) 0.8417(5) 0.1274(3) 0.0871(13) Uani 1 1 d D B 1
C30 C 0.2083(7) 0.7254(7) 0.1099(4) 0.152(3) Uani 1 1 d D B 1
H30A H 0.1371 0.7023 0.1037 0.182 Uiso 1 1 calc R B 1
H30B H 0.3007 0.6682 0.1039 0.182 Uiso 1 1 calc R B 1
C31 C 0.0340(5) 0.9337(7) 0.1372(5) 0.152(3) Uani 1 1 d D B 1
H31A H 0.0328 1.0106 0.1494 0.227 Uiso 1 1 calc R B 1
H31B H -0.0108 0.8947 0.1885 0.227 Uiso 1 1 calc R B 1
H31C H -0.0146 0.9564 0.0802 0.227 Uiso 1 1 calc R B 1
C32 C 0.5130(4) 0.7063(3) 0.2912(2) 0.0607(8) Uani 1 1 d . B 1
N1 N 0.6937(2) 1.0117(2) 0.43300(16) 0.0448(5) Uani 1 1 d . A 1
N2 N 0.5362(2) 0.8390(2) 0.13769(17) 0.0503(6) Uani 1 1 d . B 1
O1 O 0.6882(2) 0.8590(2) 0.58274(15) 0.0601(6) Uani 1 1 d . A 1
O2 O 0.6222(2) 0.83932(19) 0.43472(16) 0.0580(6) Uani 1 1 d . A 1
O3 O 0.9991(2) 1.0083(3) 0.38431(19) 0.0806(8) Uani 1 1 d . A 1
O4 O 0.8207(2) 1.1999(2) 0.33414(16) 0.0651(6) Uani 1 1 d . A 1
O5 O 0.7413(3) 0.8869(3) 0.1127(3) 0.0980(10) Uani 1 1 d . B 1
O6 O 0.6473(3) 0.8561(3) -0.01909(18) 0.0904(9) Uani 1 1 d . B 1
O7 O 0.5998(3) 0.5989(2) 0.32067(19) 0.0910(9) Uani 1 1 d . B 1
O8 O 0.3753(3) 0.7348(2) 0.29694(15) 0.0637(6) Uani 1 1 d . B 1
S1 S 0.71007(7) 0.86522(6) 0.48429(5) 0.0459(2) Uani 1 1 d . A 1
S2 S 0.68103(8) 0.81979(7) 0.07855(7) 0.0633(3) Uani 1 1 d . B 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0399(14) 0.0369(13) 0.0487(17) -0.0070(11) -0.0002(12) -0.0128(11)
C2 0.061(2) 0.065(2) 0.064(2) -0.0193(17) -0.0111(17) 0.0035(17)
C3 0.071(2) 0.067(2) 0.067(2) -0.0232(18) 0.0128(19) -0.0032(18)
C4 0.0448(16) 0.0326(14) 0.080(2) -0.0031(14) 0.0049(16) -0.0120(12)
C5 0.0467(17) 0.0563(19) 0.072(2) -0.0008(16) -0.0104(17) -0.0078(15)
C6 0.0512(17) 0.0573(18) 0.055(2) -0.0063(14) -0.0047(15) -0.0107(15)
C7 0.0510(19) 0.0468(19) 0.123(4) -0.0089(19) 0.016(2) -0.0046(15)
C8 0.0447(15) 0.0478(16) 0.0521(18) -0.0110(13) -0.0057(13) -0.0163(13)
C9 0.0464(16) 0.0440(16) 0.0582(19) -0.0027(13) -0.0040(14) -0.0170(13)
C10 0.0539(17) 0.0475(16) 0.066(2) -0.0115(14) 0.0058(15) -0.0227(14)
C11 0.0521(17) 0.0518(17) 0.063(2) -0.0254(14) 0.0064(15) -0.0246(14)
C12 0.0356(13) 0.0531(16) 0.0496(17) -0.0157(12) -0.0039(12) -0.0175(12)
C13 0.095(3) 0.064(2) 0.066(2) 0.0059(18) -0.023(2) -0.032(2)
C14 0.210(14) 0.267(17) 0.100(8) 0.092(9) -0.112(9) -0.182(14)
C15 0.187(14) 0.193(15) 0.086(7) 0.051(8) -0.043(9) -0.126(13)
C13A 0.095(3) 0.064(2) 0.066(2) 0.0059(18) -0.023(2) -0.032(2)
C14A 0.184(16) 0.083(8) 0.078(8) 0.024(6) -0.021(9) 0.000(9)
C15A 0.202(15) 0.102(8) 0.040(5) -0.002(5) -0.012(7) -0.036(8)
C16 0.0438(17) 0.078(2) 0.065(2) -0.0308(18) 0.0061(15) -0.0302(17)
C17 0.0547(18) 0.0524(18) 0.059(2) -0.0105(15) 0.0087(16) -0.0155(15)
C18 0.071(2) 0.077(3) 0.087(3) -0.022(2) -0.012(2) 0.001(2)
C19 0.089(3) 0.087(3) 0.092(4) -0.001(3) 0.006(3) 0.013(3)
C20 0.103(4) 0.058(3) 0.097(4) 0.003(2) 0.043(3) -0.002(2)
C21 0.156(5) 0.077(3) 0.142(5) -0.059(3) 0.034(4) -0.035(4)
C22 0.121(4) 0.081(3) 0.091(3) -0.030(2) -0.009(3) -0.028(3)
C23 0.159(5) 0.060(3) 0.177(6) 0.012(3) 0.097(5) 0.018(3)
C24 0.0636(19) 0.070(2) 0.0465(18) -0.0125(14) 0.0016(15) -0.0355(17)
C25 0.0507(17) 0.071(2) 0.0522(19) -0.0031(15) -0.0014(14) -0.0339(16)
C26 0.0497(17) 0.0623(19) 0.0514(19) -0.0109(14) 0.0031(14) -0.0198(15)
C27 0.0509(17) 0.0530(17) 0.067(2) -0.0206(15) -0.0052(15) -0.0144(14)
C28 0.0468(16) 0.0475(16) 0.060(2) -0.0143(14) -0.0093(14) -0.0154(13)
C29 0.080(3) 0.147(4) 0.059(2) -0.008(2) -0.005(2) -0.077(3)
C30 0.163(6) 0.255(8) 0.153(6) -0.118(6) 0.050(4) -0.167(6)
C31 0.073(3) 0.221(7) 0.176(6) -0.020(5) -0.022(4) -0.085(4)
C32 0.072(2) 0.0522(19) 0.0498(19) -0.0077(14) -0.0075(17) -0.0194(17)
N1 0.0391(12) 0.0384(12) 0.0516(14) -0.0066(10) -0.0097(11) -0.0110(10)
N2 0.0437(13) 0.0513(14) 0.0525(15) -0.0076(11) -0.0017(11) -0.0189(11)
O1 0.0529(12) 0.0609(13) 0.0553(14) -0.0109(10) 0.0095(10) -0.0177(10)
O2 0.0470(11) 0.0482(11) 0.0808(16) -0.0114(10) -0.0108(11) -0.0213(9)
O3 0.0373(12) 0.121(2) 0.0854(19) -0.0473(16) 0.0080(11) -0.0233(13)
O4 0.0584(13) 0.0816(16) 0.0647(15) -0.0131(12) 0.0096(11) -0.0428(13)
O5 0.0602(15) 0.0723(17) 0.176(3) -0.0421(18) 0.0172(17) -0.0388(14)
O6 0.0720(16) 0.0886(18) 0.0598(16) 0.0220(13) 0.0144(13) -0.0140(14)
O7 0.103(2) 0.0514(14) 0.0841(19) 0.0069(12) -0.0200(16) -0.0084(14)
O8 0.0739(15) 0.0615(13) 0.0524(13) 0.0019(10) 0.0008(11) -0.0345(12)
S1 0.0365(4) 0.0406(4) 0.0546(5) -0.0088(3) 0.0006(3) -0.0124(3)
S2 0.0472(4) 0.0481(4) 0.0818(6) -0.0034(4) 0.0093(4) -0.0179(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(4) . ?
C1 C6 1.376(4) . ?
C1 S1 1.765(3) . ?
C2 C3 1.394(5) . ?
C3 C4 1.377(5) . ?
C4 C5 1.366(5) . ?
C4 C7 1.514(4) . ?
C5 C6 1.386(4) . ?
C8 N1 1.471(4) . ?
C8 C9 1.533(4) . ?
C9 C13 1.518(5) . ?
C9 C10 1.531(4) . ?
C10 O4 1.466(4) . ?
C10 C11 1.518(5) . ?
C11 C12 1.515(4) . ?
C12 N1 1.469(3) . ?
C12 C16 1.529(4) . ?
C13 C14 1.379(7) . ?
C13 C15 1.405(7) . ?
C16 O3 1.200(4) . ?
C16 O4 1.349(4) . ?
C17 C22 1.362(5) . ?
C17 C18 1.366(5) . ?
C17 S2 1.760(3) . ?
C18 C19 1.365(6) . ?
C19 C20 1.357(8) . ?
C20 C21 1.367(8) . ?
C20 C23 1.518(6) . ?
C21 C22 1.420(7) . ?
C24 N2 1.467(4) . ?
C24 C25 1.523(4) . ?
C25 C29 1.507(5) . ?
C25 C26 1.531(4) . ?
C26 O8 1.460(4) . ?
C26 C27 1.524(4) . ?
C27 C28 1.510(4) . ?
C28 N2 1.461(4) . ?
C28 C32 1.524(4) . ?
C29 C30 1.347(6) . ?
C29 C31 1.456(6) . ?
C32 O7 1.199(4) . ?
C32 O8 1.353(4) . ?
N1 S1 1.625(2) . ?
N2 S2 1.627(3) . ?
O1 S1 1.428(2) . ?
O2 S1 1.430(2) . ?
O5 S2 1.420(3) . ?
O6 S2 1.436(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.7(3) . . ?
C2 C1 S1 119.7(2) . . ?
C6 C1 S1 119.6(2) . . ?
C1 C2 C3 119.0(3) . . ?
C4 C3 C2 121.0(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C7 121.2(3) . . ?
C3 C4 C7 120.2(3) . . ?
C4 C5 C6 121.5(3) . . ?
C1 C6 C5 119.1(3) . . ?
N1 C8 C9 110.1(2) . . ?
C13 C9 C10 115.4(3) . . ?
C13 C9 C8 111.3(3) . . ?
C10 C9 C8 110.1(2) . . ?
O4 C10 C11 102.4(2) . . ?
O4 C10 C9 109.1(2) . . ?
C11 C10 C9 110.6(2) . . ?
C12 C11 C10 98.3(2) . . ?
N1 C12 C11 108.4(2) . . ?
N1 C12 C16 108.2(2) . . ?
C11 C12 C16 100.5(3) . . ?
C14 C13 C15 122.6(6) . . ?
C14 C13 C9 115.1(5) . . ?
C15 C13 C9 119.6(5) . . ?
O3 C16 O4 122.5(3) . . ?
O3 C16 C12 129.2(3) . . ?
O4 C16 C12 108.2(2) . . ?
C22 C17 C18 120.5(4) . . ?
C22 C17 S2 120.0(3) . . ?
C18 C17 S2 119.5(3) . . ?
C19 C18 C17 120.5(5) . . ?
C20 C19 C18 121.6(5) . . ?
C19 C20 C21 118.1(4) . . ?
C19 C20 C23 122.4(6) . . ?
C21 C20 C23 119.5(6) . . ?
C20 C21 C22 121.7(5) . . ?
C17 C22 C21 117.6(5) . . ?
N2 C24 C25 110.8(3) . . ?
C29 C25 C24 115.4(3) . . ?
C29 C25 C26 112.1(3) . . ?
C24 C25 C26 109.7(3) . . ?
O8 C26 C27 102.8(2) . . ?
O8 C26 C25 109.3(3) . . ?
C27 C26 C25 110.4(3) . . ?
C28 C27 C26 97.9(2) . . ?
N2 C28 C27 107.8(2) . . ?
N2 C28 C32 109.3(2) . . ?
C27 C28 C32 100.8(3) . . ?
C30 C29 C31 121.5(5) . . ?
C30 C29 C25 122.3(4) . . ?
C31 C29 C25 116.1(4) . . ?
O7 C32 O8 122.5(3) . . ?
O7 C32 C28 129.3(4) . . ?
O8 C32 C28 108.2(3) . . ?
C12 N1 C8 115.3(2) . . ?
C12 N1 S1 118.79(18) . . ?
C8 N1 S1 121.51(19) . . ?
C28 N2 C24 115.1(2) . . ?
C28 N2 S2 119.9(2) . . ?
C24 N2 S2 119.8(2) . . ?
C16 O4 C10 108.5(2) . . ?
C32 O8 C26 108.4(2) . . ?
O1 S1 O2 119.93(14) . . ?
O1 S1 N1 107.16(13) . . ?
O2 S1 N1 106.06(12) . . ?
O1 S1 C1 106.68(13) . . ?
O2 S1 C1 108.48(13) . . ?
N1 S1 C1 108.05(13) . . ?
O5 S2 O6 119.80(19) . . ?
O5 S2 N2 106.37(16) . . ?
O6 S2 N2 106.58(14) . . ?
O5 S2 C17 107.50(17) . . ?
O6 S2 C17 107.49(17) . . ?
N2 S2 C17 108.74(14) . . ?

_diffrn_measured_fraction_theta_max 0.868
_diffrn_reflns_theta_full        70.66
_diffrn_measured_fraction_theta_full 0.868
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.051

# Attachment 'Compound26b.cif'

data_clc512g
_database_code_depnum_ccdc_archive 'CCDC 689105'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 N O3 S'
_chemical_formula_sum            'C21 H25 N O3 S'
_chemical_formula_weight         371.48

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   9.6771(12)
_cell_length_b                   8.3153(12)
_cell_length_c                   12.6634(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.075(7)
_cell_angle_gamma                90.00
_cell_volume                     992.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3237
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      25.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9305
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6142
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.16
_reflns_number_total             3400
_reflns_number_gt                3237
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0320P)^2^+0.2130P] where P=(Fo^2^+2Fc^2^)/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(8)
_refine_ls_number_reflns         3400
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.76759(7) 0.13508(8) 0.85658(5) 0.04856(17) Uani 1 1 d . . .
O1 O 0.6529(2) 0.7391(2) 1.04804(16) 0.0555(5) Uani 1 1 d . . .
H1A H 0.6705 0.8213 1.0178 0.083 Uiso 1 1 calc R . .
O2 O 0.90254(18) 0.1364(3) 0.82724(15) 0.0644(5) Uani 1 1 d . . .
O3 O 0.7410(3) 0.0063(2) 0.92553(17) 0.0682(7) Uani 1 1 d . . .
N1 N 0.7385(2) 0.3027(2) 0.91395(16) 0.0401(5) Uani 1 1 d . . .
C1 C 0.7487(2) 0.3016(3) 1.03279(18) 0.0388(5) Uani 1 1 d . . .
H1 H 0.6929 0.2102 1.0488 0.047 Uiso 1 1 calc R . .
C2 C 0.6782(3) 0.4546(3) 1.0614(2) 0.0422(6) Uani 1 1 d . . .
H2A H 0.5764 0.4452 1.0344 0.051 Uiso 1 1 calc R . .
H2B H 0.6966 0.4641 1.1397 0.051 Uiso 1 1 calc R . .
C3 C 0.7288(2) 0.6066(3) 1.01563(19) 0.0401(5) Uani 1 1 d . . .
H3 H 0.8302 0.6206 1.0477 0.048 Uiso 1 1 calc R . .
C4 C 0.7077(2) 0.5957(3) 0.8925(2) 0.0413(5) Uani 1 1 d . . .
H4 H 0.7512 0.6910 0.8680 0.050 Uiso 1 1 calc R . .
C5 C 0.7899(3) 0.4482(3) 0.8689(2) 0.0431(6) Uani 1 1 d . . .
H5A H 0.7780 0.4360 0.7912 0.052 Uiso 1 1 calc R . .
H5B H 0.8901 0.4626 0.9007 0.052 Uiso 1 1 calc R . .
C6 C 0.9027(2) 0.2788(3) 1.09902(19) 0.0461(6) Uani 1 1 d . . .
H6A H 0.9509 0.2012 1.0629 0.055 Uiso 1 1 calc R . .
H6B H 0.9532 0.3801 1.1026 0.055 Uiso 1 1 calc R . .
C7 C 0.9050(3) 0.2214(3) 1.2119(2) 0.0471(6) Uani 1 1 d . . .
C8 C 0.8849(3) 0.0604(4) 1.2306(3) 0.0641(8) Uani 1 1 d . . .
H8 H 0.8739 -0.0128 1.1737 0.077 Uiso 1 1 calc R . .
C9 C 0.8810(4) 0.0072(5) 1.3335(3) 0.0882(12) Uani 1 1 d . . .
H9 H 0.8682 -0.1015 1.3458 0.106 Uiso 1 1 calc R . .
C10 C 0.8959(4) 0.1146(8) 1.4168(3) 0.0990(15) Uani 1 1 d . . .
H10 H 0.8910 0.0790 1.4855 0.119 Uiso 1 1 calc R . .
C11 C 0.9179(4) 0.2744(7) 1.4002(3) 0.0941(13) Uani 1 1 d . . .
H11 H 0.9290 0.3469 1.4574 0.113 Uiso 1 1 calc R . .
C12 C 0.9235(3) 0.3268(5) 1.2981(2) 0.0699(9) Uani 1 1 d . . .
H12 H 0.9401 0.4350 1.2871 0.084 Uiso 1 1 calc R . .
C13 C 0.5543(3) 0.5912(3) 0.8333(2) 0.0472(6) Uani 1 1 d . . .
H13 H 0.5004 0.5034 0.8452 0.057 Uiso 1 1 calc R . .
C14 C 0.4916(3) 0.7022(4) 0.7661(2) 0.0635(8) Uani 1 1 d . . .
H14A H 0.5424 0.7917 0.7522 0.076 Uiso 1 1 calc R . .
H14B H 0.3962 0.6917 0.7322 0.076 Uiso 1 1 calc R . .
C15 C 0.6351(2) 0.1307(4) 0.73605(18) 0.0460(5) Uani 1 1 d . . .
C16 C 0.4949(3) 0.1562(3) 0.7376(2) 0.0531(7) Uani 1 1 d . . .
H16 H 0.4700 0.1853 0.8018 0.064 Uiso 1 1 calc R . .
C17 C 0.3917(3) 0.1383(5) 0.6435(2) 0.0621(7) Uani 1 1 d . . .
H17 H 0.2973 0.1566 0.6450 0.074 Uiso 1 1 calc R . .
C18 C 0.4248(3) 0.0942(4) 0.5475(2) 0.0724(10) Uani 1 1 d . . .
C19 C 0.5656(4) 0.0703(6) 0.5474(3) 0.0915(14) Uani 1 1 d . . .
H19 H 0.5902 0.0417 0.4831 0.110 Uiso 1 1 calc R . .
C20 C 0.6715(3) 0.0879(5) 0.6407(2) 0.0730(10) Uani 1 1 d . . .
H20 H 0.7660 0.0710 0.6391 0.088 Uiso 1 1 calc R . .
C21 C 0.3103(4) 0.0729(7) 0.4451(3) 0.1159(18) Uani 1 1 d . . .
H21A H 0.2230 0.0432 0.4638 0.174 Uiso 1 1 calc R . .
H21B H 0.3380 -0.0101 0.4013 0.174 Uiso 1 1 calc R . .
H21C H 0.2974 0.1720 0.4052 0.174 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0587(4) 0.0342(3) 0.0513(3) -0.0010(3) 0.0094(3) 0.0064(3)
O1 0.0728(13) 0.0366(10) 0.0625(13) -0.0042(9) 0.0263(10) 0.0077(9)
O2 0.0509(10) 0.0654(11) 0.0770(12) -0.0099(13) 0.0142(9) 0.0188(11)
O3 0.1129(19) 0.0295(10) 0.0587(13) 0.0093(9) 0.0119(12) -0.0003(10)
N1 0.0521(12) 0.0281(10) 0.0413(11) 0.0015(9) 0.0127(9) -0.0001(9)
C1 0.0422(13) 0.0374(12) 0.0380(12) 0.0057(10) 0.0115(10) -0.0006(10)
C2 0.0422(14) 0.0410(13) 0.0441(13) 0.0023(11) 0.0112(11) -0.0010(11)
C3 0.0425(12) 0.0303(13) 0.0481(13) -0.0015(10) 0.0118(10) 0.0010(10)
C4 0.0451(12) 0.0334(13) 0.0476(13) 0.0039(10) 0.0151(10) -0.0010(9)
C5 0.0482(15) 0.0365(12) 0.0481(14) 0.0075(11) 0.0179(12) 0.0023(11)
C6 0.0433(13) 0.0474(15) 0.0477(14) 0.0041(12) 0.0104(11) -0.0005(11)
C7 0.0400(13) 0.0535(16) 0.0445(15) 0.0037(12) 0.0026(11) 0.0006(12)
C8 0.067(2) 0.0565(18) 0.067(2) 0.0140(15) 0.0124(16) 0.0026(15)
C9 0.081(3) 0.093(3) 0.089(3) 0.048(2) 0.018(2) 0.001(2)
C10 0.073(2) 0.169(5) 0.055(2) 0.031(3) 0.0152(16) 0.020(3)
C11 0.077(2) 0.142(4) 0.057(2) -0.018(3) 0.0032(18) 0.015(3)
C12 0.065(2) 0.081(2) 0.0570(19) -0.0106(17) -0.0002(15) -0.0022(17)
C13 0.0477(13) 0.0417(15) 0.0518(14) 0.0008(11) 0.0103(11) -0.0014(11)
C14 0.0617(18) 0.0570(17) 0.065(2) 0.0066(14) 0.0012(14) 0.0088(14)
C15 0.0534(13) 0.0397(12) 0.0467(12) -0.0031(13) 0.0150(10) -0.0020(14)
C16 0.0598(15) 0.0517(16) 0.0515(14) -0.0070(14) 0.0203(12) -0.0017(14)
C17 0.0512(14) 0.0717(17) 0.0641(17) -0.0061(19) 0.0147(12) -0.0039(17)
C18 0.0663(18) 0.097(3) 0.0533(17) -0.0083(17) 0.0114(14) -0.0136(19)
C19 0.073(2) 0.154(4) 0.0501(18) -0.030(2) 0.0205(16) -0.016(2)
C20 0.0568(16) 0.108(3) 0.0588(18) -0.0189(18) 0.0221(14) -0.0009(17)
C21 0.094(3) 0.187(6) 0.058(2) -0.016(3) -0.0002(19) -0.031(3)

_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 O2 1.4364(18) . ?
S1 O3 1.441(2) . ?
S1 N1 1.625(2) . ?
S1 C15 1.758(2) . ?
O1 C3 1.435(3) . ?
N1 C5 1.471(3) . ?
N1 C1 1.486(3) . ?
C1 C2 1.525(3) . ?
C1 C6 1.547(3) . ?
C2 C3 1.517(3) . ?
C3 C4 1.528(3) . ?
C4 C13 1.505(3) . ?
C4 C5 1.528(3) . ?
C6 C7 1.503(3) . ?
C7 C12 1.379(4) . ?
C7 C8 1.381(4) . ?
C8 C9 1.385(5) . ?
C9 C10 1.365(6) . ?
C10 C11 1.369(7) . ?
C11 C12 1.377(5) . ?
C13 C14 1.308(4) . ?
C15 C16 1.378(3) . ?
C15 C20 1.378(3) . ?
C16 C17 1.379(4) . ?
C17 C18 1.375(4) . ?
C18 C19 1.377(4) . ?
C18 C21 1.513(5) . ?
C19 C20 1.386(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 117.38(14) . . ?
O2 S1 N1 111.61(12) . . ?
O3 S1 N1 107.08(11) . . ?
O2 S1 C15 107.62(11) . . ?
O3 S1 C15 108.39(14) . . ?
N1 S1 C15 103.90(12) . . ?
C5 N1 C1 116.5(2) . . ?
C5 N1 S1 115.10(16) . . ?
C1 N1 S1 117.98(16) . . ?
N1 C1 C2 107.7(2) . . ?
N1 C1 C6 112.64(19) . . ?
C2 C1 C6 113.6(2) . . ?
C3 C2 C1 113.83(19) . . ?
O1 C3 C2 107.48(18) . . ?
O1 C3 C4 112.23(19) . . ?
C2 C3 C4 111.11(19) . . ?
C13 C4 C5 112.4(2) . . ?
C13 C4 C3 113.53(19) . . ?
C5 C4 C3 106.97(19) . . ?
N1 C5 C4 110.39(19) . . ?
C7 C6 C1 111.1(2) . . ?
C12 C7 C8 118.6(3) . . ?
C12 C7 C6 121.5(3) . . ?
C8 C7 C6 119.9(3) . . ?
C7 C8 C9 120.3(4) . . ?
C10 C9 C8 119.9(4) . . ?
C9 C10 C11 120.6(4) . . ?
C10 C11 C12 119.5(4) . . ?
C11 C12 C7 121.1(4) . . ?
C14 C13 C4 124.6(3) . . ?
C16 C15 C20 120.0(2) . . ?
C16 C15 S1 120.75(18) . . ?
C20 C15 S1 119.0(2) . . ?
C15 C16 C17 119.6(2) . . ?
C18 C17 C16 121.6(3) . . ?
C17 C18 C19 117.9(3) . . ?
C17 C18 C21 121.1(3) . . ?
C19 C18 C21 121.0(3) . . ?
C18 C19 C20 121.7(3) . . ?
C15 C20 C19 119.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.16
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.034