# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_20150112_0m
_database_code_depnum_ccdc_archive 'CCDC 1400877'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        20150112
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N O7 S'
_chemical_formula_weight         395.42

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.6015(2)
_cell_length_b                   16.8605(4)
_cell_length_c                   17.1484(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1908.70(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    2735
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      18.54

_exptl_crystal_description       Block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9515
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53487
_diffrn_reflns_av_R_equivalents  0.1093
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.32
_reflns_number_total             4748
_reflns_number_gt                2185
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1111P)²+0.0190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_number_reflns         4748
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1579
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.2193
_refine_ls_wR_factor_gt          0.1734
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.1965(2) 0.57620(8) 0.01619(7) 0.0829(5) Uani 1 1 d . . .
N1 N 0.3043(6) 0.54440(18) -0.06443(18) 0.0602(9) Uani 1 1 d . . .
O1 O -0.0063(6) 0.5983(3) 0.0042(3) 0.1316(17) Uani 1 1 d . . .
O2 O 0.2360(13) 0.5275(4) 0.0768(3) 0.197(4) Uani 1 1 d . . .
O3 O 0.3164(10) 0.6525(4) 0.0248(3) 0.180(3) Uani 1 1 d . . .
O4 O 1.1369(5) 0.75680(19) -0.1286(2) 0.0752(9) Uani 1 1 d . . .
O5 O 1.1395(6) 0.8385(2) -0.2296(3) 0.1098(14) Uani 1 1 d . . .
O6 O 0.1698(9) 0.3232(3) -0.0853(3) 0.1271(15) Uani 1 1 d . . .
O7 O -0.0769(7) 0.4106(2) -0.0710(2) 0.1053(12) Uani 1 1 d . . .
C1 C 0.4752(8) 0.6668(3) -0.0257(3) 0.0736(13) Uani 1 1 d . . .
H1B H 0.6018 0.6706 0.0028 0.088 Uiso 1 1 calc R . .
H1C H 0.4536 0.7160 -0.0538 0.088 Uiso 1 1 calc R . .
C2 C 0.4805(6) 0.5958(2) -0.0828(2) 0.0577(10) Uani 1 1 d . . .
H2B H 0.6069 0.5660 -0.0765 0.069 Uiso 1 1 calc R . .
C3 C 0.4484(6) 0.6166(2) -0.1675(2) 0.0532(10) Uani 1 1 d . . .
C4 C 0.5695(7) 0.6646(2) -0.2148(2) 0.0577(10) Uani 1 1 d . . .
C5 C 0.4990(7) 0.6774(3) -0.2915(3) 0.0677(12) Uani 1 1 d . . .
H5A H 0.5727 0.7102 -0.3246 0.081 Uiso 1 1 calc R . .
C6 C 0.3258(8) 0.6429(3) -0.3182(3) 0.0740(13) Uani 1 1 d . . .
H6A H 0.2849 0.6520 -0.3693 0.089 Uiso 1 1 calc R . .
C7 C 0.2098(7) 0.5946(3) -0.2710(3) 0.0695(12) Uani 1 1 d . . .
H7A H 0.0918 0.5711 -0.2895 0.083 Uiso 1 1 calc R . .
C8 C 0.2744(7) 0.5823(2) -0.1951(2) 0.0607(11) Uani 1 1 d . . .
C9 C 0.1767(7) 0.5300(2) -0.1338(2) 0.0640(11) Uani 1 1 d . . .
H9A H 0.0371 0.5471 -0.1240 0.077 Uiso 1 1 calc R . .
C10 C 0.7566(6) 0.6991(2) -0.1861(2) 0.0594(11) Uani 1 1 d . . .
H10A H 0.7987 0.6832 -0.1367 0.071 Uiso 1 1 calc R . .
C11 C 0.8712(6) 0.7497(3) -0.2221(3) 0.0681(12) Uani 1 1 d . . .
H11A H 0.8326 0.7673 -0.2713 0.082 Uiso 1 1 calc R . .
C12 C 1.0626(8) 0.7805(3) -0.1875(3) 0.0667(12) Uani 1 1 d . . .
C13 C 1.3245(10) 0.8748(4) -0.1998(5) 0.132(3) Uani 1 1 d . . .
H13A H 1.3358 0.8653 -0.1442 0.158 Uiso 1 1 calc R . .
H13B H 1.4416 0.8516 -0.2253 0.158 Uiso 1 1 calc R . .
C14 C 1.3177(11) 0.9573(4) -0.2147(4) 0.121(2) Uani 1 1 d . . .
H14A H 1.4396 0.9817 -0.1958 0.181 Uiso 1 1 calc R . .
H14B H 1.2030 0.9801 -0.1886 0.181 Uiso 1 1 calc R . .
H14C H 1.3059 0.9662 -0.2698 0.181 Uiso 1 1 calc R . .
C15 C 0.1815(9) 0.4428(3) -0.1569(3) 0.0784(13) Uani 1 1 d . . .
H15A H 0.1093 0.4368 -0.2058 0.094 Uiso 1 1 calc R . .
H15B H 0.3213 0.4278 -0.1661 0.094 Uiso 1 1 calc R . .
C16 C 0.0933(10) 0.3867(4) -0.0993(4) 0.0877(16) Uani 1 1 d . . .
C17 C -0.1778(16) 0.3556(5) -0.0162(5) 0.151(3) Uani 1 1 d . . .
H17A H -0.2275 0.3098 -0.0446 0.181 Uiso 1 1 calc R . .
H17B H -0.0809 0.3373 0.0223 0.181 Uiso 1 1 calc R . .
C18 C -0.3356(15) 0.3925(6) 0.0204(6) 0.188(4) Uani 1 1 d . . .
H18A H -0.3980 0.3563 0.0564 0.282 Uiso 1 1 calc R . .
H18B H -0.4335 0.4091 -0.0177 0.282 Uiso 1 1 calc R . .
H18C H -0.2863 0.4379 0.0482 0.282 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
S1 O2 1.351(5) . ?
S1 O1 1.405(4) . ?
S1 O3 1.518(5) . ?
S1 N1 1.645(3) . ?
N1 C9 1.478(5) . ?
N1 C2 1.484(5) . ?
O3 C1 1.381(6) . ?
O4 C12 1.191(5) . ?
O5 C12 1.318(6) . ?
O5 C13 1.458(7) . ?
O6 C16 1.208(7) . ?
O7 C16 1.289(7) . ?
O7 C17 1.478(7) . ?
C1 C2 1.548(6) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.509(6) . ?
C2 H2B 0.9800 . ?
C3 C8 1.369(6) . ?
C3 C4 1.397(6) . ?
C4 C5 1.413(6) . ?
C4 C10 1.451(6) . ?
C5 C6 1.362(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.380(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.385(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.515(6) . ?
C9 C15 1.523(6) . ?
C9 H9A 0.9800 . ?
C10 C11 1.297(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.490(7) . ?
C11 H11A 0.9300 . ?
C13 C14 1.416(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.486(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.367(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O2 S1 O1 117.2(4) . . ?
O2 S1 O3 109.9(5) . . ?
O1 S1 O3 106.7(4) . . ?
O2 S1 N1 111.4(3) . . ?
O1 S1 N1 112.1(2) . . ?
O3 S1 N1 97.6(2) . . ?
C9 N1 C2 111.8(3) . . ?
C9 N1 S1 118.9(3) . . ?
C2 N1 S1 109.1(3) . . ?
C1 O3 S1 118.9(3) . . ?
C12 O5 C13 116.2(4) . . ?
C16 O7 C17 115.9(6) . . ?
O3 C1 C2 106.2(4) . . ?
O3 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
O3 C1 H1C 110.5 . . ?
C2 C1 H1C 110.5 . . ?
H1B C1 H1C 108.7 . . ?
N1 C2 C3 103.3(3) . . ?
N1 C2 C1 107.4(3) . . ?
C3 C2 C1 115.2(3) . . ?
N1 C2 H2B 110.2 . . ?
C3 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
C8 C3 C4 121.6(4) . . ?
C8 C3 C2 110.6(4) . . ?
C4 C3 C2 127.8(4) . . ?
C3 C4 C5 116.1(4) . . ?
C3 C4 C10 121.5(4) . . ?
C5 C4 C10 122.4(4) . . ?
C6 C5 C4 121.7(4) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C7 121.3(4) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C6 C7 C8 118.0(4) . . ?
C6 C7 H7A 121.0 . . ?
C8 C7 H7A 121.0 . . ?
C3 C8 C7 121.3(4) . . ?
C3 C8 C9 111.3(4) . . ?
C7 C8 C9 127.4(4) . . ?
N1 C9 C8 102.7(3) . . ?
N1 C9 C15 110.8(4) . . ?
C8 C9 C15 111.9(4) . . ?
N1 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
C15 C9 H9A 110.4 . . ?
C11 C10 C4 126.8(4) . . ?
C11 C10 H10A 116.6 . . ?
C4 C10 H10A 116.6 . . ?
C10 C11 C12 122.3(4) . . ?
C10 C11 H11A 118.9 . . ?
C12 C11 H11A 118.9 . . ?
O4 C12 O5 123.7(5) . . ?
O4 C12 C11 124.8(4) . . ?
O5 C12 C11 111.5(4) . . ?
C14 C13 O5 108.8(6) . . ?
C14 C13 H13A 109.9 . . ?
O5 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
O5 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
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 . . ?
C16 C15 C9 115.7(4) . . ?
C16 C15 H15A 108.4 . . ?
C9 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
C9 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
O6 C16 O7 124.5(6) . . ?
O6 C16 C15 122.2(6) . . ?
O7 C16 C15 113.2(5) . . ?
C18 C17 O7 110.5(7) . . ?
C18 C17 H17A 109.6 . . ?
O7 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
O7 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
O2 S1 N1 C9 123.8(5) . . . . ?
O1 S1 N1 C9 -9.8(4) . . . . ?
O3 S1 N1 C9 -121.3(4) . . . . ?
O2 S1 N1 C2 -106.4(5) . . . . ?
O1 S1 N1 C2 120.0(4) . . . . ?
O3 S1 N1 C2 8.5(4) . . . . ?
O2 S1 O3 C1 109.8(6) . . . . ?
O1 S1 O3 C1 -122.2(6) . . . . ?
N1 S1 O3 C1 -6.3(7) . . . . ?
S1 O3 C1 C2 1.8(8) . . . . ?
C9 N1 C2 C3 3.1(4) . . . . ?
S1 N1 C2 C3 -130.5(3) . . . . ?
C9 N1 C2 C1 125.3(4) . . . . ?
S1 N1 C2 C1 -8.3(4) . . . . ?
O3 C1 C2 N1 4.4(6) . . . . ?
O3 C1 C2 C3 118.8(5) . . . . ?
N1 C2 C3 C8 0.5(4) . . . . ?
C1 C2 C3 C8 -116.3(4) . . . . ?
N1 C2 C3 C4 179.4(4) . . . . ?
C1 C2 C3 C4 62.5(6) . . . . ?
C8 C3 C4 C5 1.7(6) . . . . ?
C2 C3 C4 C5 -177.1(4) . . . . ?
C8 C3 C4 C10 -178.3(4) . . . . ?
C2 C3 C4 C10 3.0(6) . . . . ?
C3 C4 C5 C6 -1.8(6) . . . . ?
C10 C4 C5 C6 178.2(4) . . . . ?
C4 C5 C6 C7 0.9(7) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C4 C3 C8 C7 -0.7(6) . . . . ?
C2 C3 C8 C7 178.2(4) . . . . ?
C4 C3 C8 C9 177.2(3) . . . . ?
C2 C3 C8 C9 -3.9(5) . . . . ?
C6 C7 C8 C3 -0.2(6) . . . . ?
C6 C7 C8 C9 -177.8(4) . . . . ?
C2 N1 C9 C8 -5.1(4) . . . . ?
S1 N1 C9 C8 123.4(3) . . . . ?
C2 N1 C9 C15 114.5(4) . . . . ?
S1 N1 C9 C15 -116.9(4) . . . . ?
C3 C8 C9 N1 5.5(4) . . . . ?
C7 C8 C9 N1 -176.8(4) . . . . ?
C3 C8 C9 C15 -113.4(4) . . . . ?
C7 C8 C9 C15 64.4(6) . . . . ?
C3 C4 C10 C11 -173.6(4) . . . . ?
C5 C4 C10 C11 6.4(7) . . . . ?
C4 C10 C11 C12 -179.1(4) . . . . ?
C13 O5 C12 O4 -0.9(8) . . . . ?
C13 O5 C12 C11 178.3(5) . . . . ?
C10 C11 C12 O4 7.4(7) . . . . ?
C10 C11 C12 O5 -171.7(4) . . . . ?
C12 O5 C13 C14 -142.5(6) . . . . ?
N1 C9 C15 C16 64.6(6) . . . . ?
C8 C9 C15 C16 178.6(5) . . . . ?
C17 O7 C16 O6 1.6(9) . . . . ?
C17 O7 C16 C15 177.1(6) . . . . ?
C9 C15 C16 O6 -139.7(6) . . . . ?
C9 C15 C16 O7 44.7(7) . . . . ?
C16 O7 C17 C18 169.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_20150429_0m
_database_code_depnum_ccdc_archive 'CCDC 1400887'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        20150429
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 N O7 S'
_chemical_formula_weight         381.39

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

_cell_length_a                   6.20840(10)
_cell_length_b                   13.7420(2)
_cell_length_c                   21.5303(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1836.88(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    4874
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      19.81

_exptl_crystal_description       Block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9423
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49437
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4571
_reflns_number_gt                2656
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0695P)²+0.6267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_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   -0.01(13)
_refine_ls_number_reflns         4571
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
S1 S 0.31005(15) 0.43742(7) 0.84624(4) 0.0544(3) Uani 1 1 d . . .
O1 O 0.3059(8) 0.4479(3) 0.90949(14) 0.151(2) Uani 1 1 d . . .
O2 O 0.5067(5) 0.4506(2) 0.81651(17) 0.0887(10) Uani 1 1 d . . .
O3 O 0.1429(7) 0.5082(3) 0.8214(2) 0.150(2) Uani 1 1 d . . .
O4 O -0.6631(4) 0.4845(2) 0.65905(13) 0.0740(8) Uani 1 1 d . . .
O5 O -0.6940(4) 0.4390(2) 0.56015(11) 0.0715(8) Uani 1 1 d . . .
O6 O 0.5794(7) 0.2278(3) 0.90014(18) 0.1194(15) Uani 1 1 d . . .
O7 O 0.3152(5) 0.1374(2) 0.93948(14) 0.0823(9) Uani 1 1 d . . .
N1 N 0.1870(5) 0.3383(2) 0.82355(12) 0.0492(7) Uani 1 1 d . . .
C1 C 0.0068(7) 0.4736(3) 0.77571(18) 0.0569(10) Uani 1 1 d . . .
H1B H 0.0627 0.4893 0.7348 0.068 Uiso 1 1 calc R . .
H1C H -0.1354 0.5021 0.7799 0.068 Uiso 1 1 calc R . .
C2 C -0.0028(6) 0.3641(3) 0.78491(14) 0.0456(8) Uani 1 1 d . . .
H2B H -0.1366 0.3456 0.8060 0.055 Uiso 1 1 calc R . .
C3 C 0.0275(6) 0.3047(2) 0.72643(16) 0.0434(8) Uani 1 1 d . . .
C4 C -0.0976(6) 0.3038(3) 0.67201(15) 0.0473(8) Uani 1 1 d . . .
C5 C -0.0232(7) 0.2448(3) 0.62350(17) 0.0594(10) Uani 1 1 d . . .
H5A H -0.1039 0.2421 0.5872 0.071 Uiso 1 1 calc R . .
C6 C 0.1634(7) 0.1903(3) 0.62664(17) 0.0605(10) Uani 1 1 d . . .
C7 C 0.2818(7) 0.1920(2) 0.68168(17) 0.0571(10) Uani 1 1 d . . .
H7A H 0.4066 0.1550 0.6853 0.069 Uiso 1 1 calc R . .
C8 C 0.2136(6) 0.2486(2) 0.73074(15) 0.0457(8) Uani 1 1 d . . .
C9 C 0.3152(6) 0.2598(3) 0.79317(16) 0.0520(8) Uani 1 1 d . . .
H9A H 0.4651 0.2810 0.7884 0.062 Uiso 1 1 calc R . .
C10 C -0.2895(6) 0.3630(2) 0.66672(15) 0.0493(8) Uani 1 1 d . . .
H10A H -0.3345 0.3946 0.7027 0.059 Uiso 1 1 calc R . .
C11 C -0.4093(6) 0.3774(3) 0.61597(18) 0.0573(10) Uani 1 1 d . . .
H11A H -0.3692 0.3469 0.5792 0.069 Uiso 1 1 calc R . .
C12 C -0.5983(6) 0.4384(3) 0.61602(17) 0.0555(9) Uani 1 1 d . . .
C13 C -0.8856(7) 0.4988(4) 0.5555(2) 0.0827(14) Uani 1 1 d . . .
H13A H -0.9416 0.4955 0.5140 0.124 Uiso 1 1 calc R . .
H13B H -0.8500 0.5651 0.5653 0.124 Uiso 1 1 calc R . .
H13C H -0.9923 0.4756 0.5842 0.124 Uiso 1 1 calc R . .
C14 C 0.2394(10) 0.1310(3) 0.5723(2) 0.0942(16) Uani 1 1 d . . .
H14A H 0.3702 0.0979 0.5832 0.141 Uiso 1 1 calc R . .
H14B H 0.2653 0.1731 0.5375 0.141 Uiso 1 1 calc R . .
H14C H 0.1311 0.0840 0.5615 0.141 Uiso 1 1 calc R . .
C15 C 0.3066(8) 0.1672(3) 0.83237(18) 0.0742(12) Uani 1 1 d . . .
H15A H 0.1576 0.1490 0.8394 0.089 Uiso 1 1 calc R . .
H15B H 0.3763 0.1145 0.8102 0.089 Uiso 1 1 calc R . .
C16 C 0.4172(9) 0.1826(3) 0.8936(2) 0.0790(14) Uani 1 1 d . . .
C17 C 0.4023(10) 0.1492(4) 1.0016(2) 0.109(2) Uani 1 1 d . . .
H17A H 0.3154 0.1137 1.0306 0.163 Uiso 1 1 calc R . .
H17B H 0.4020 0.2170 1.0125 0.163 Uiso 1 1 calc R . .
H17C H 0.5472 0.1249 1.0027 0.163 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
S1 O1 1.370(3) . ?
S1 O2 1.390(3) . ?
S1 O3 1.519(4) . ?
S1 N1 1.636(3) . ?
O3 C1 1.381(5) . ?
O4 C12 1.192(4) . ?
O5 C12 1.341(4) . ?
O5 C13 1.450(5) . ?
O6 C16 1.191(6) . ?
O7 C16 1.327(6) . ?
O7 C17 1.452(5) . ?
N1 C2 1.486(4) . ?
N1 C9 1.492(5) . ?
C1 C2 1.519(5) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.512(5) . ?
C2 H2B 0.9800 . ?
C3 C8 1.392(5) . ?
C3 C4 1.406(5) . ?
C4 C5 1.401(5) . ?
C4 C10 1.447(5) . ?
C5 C6 1.381(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.395(5) . ?
C6 C14 1.501(5) . ?
C7 C8 1.379(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.493(5) . ?
C9 C15 1.528(5) . ?
C9 H9A 0.9800 . ?
C10 C11 1.337(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.442(5) . ?
C11 H11A 0.9300 . ?
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 C16 1.502(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O1 S1 O2 117.4(3) . . ?
O1 S1 O3 105.6(3) . . ?
O2 S1 O3 110.8(3) . . ?
O1 S1 N1 112.1(2) . . ?
O2 S1 N1 112.39(17) . . ?
O3 S1 N1 96.26(17) . . ?
C1 O3 S1 116.6(3) . . ?
C12 O5 C13 115.4(3) . . ?
C16 O7 C17 117.0(4) . . ?
C2 N1 C9 110.5(2) . . ?
C2 N1 S1 109.8(2) . . ?
C9 N1 S1 118.9(2) . . ?
O3 C1 C2 105.8(3) . . ?
O3 C1 H1B 110.6 . . ?
C2 C1 H1B 110.6 . . ?
O3 C1 H1C 110.6 . . ?
C2 C1 H1C 110.6 . . ?
H1B C1 H1C 108.7 . . ?
N1 C2 C3 103.8(3) . . ?
N1 C2 C1 106.1(3) . . ?
C3 C2 C1 114.9(3) . . ?
N1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C8 C3 C4 120.6(3) . . ?
C8 C3 C2 110.3(3) . . ?
C4 C3 C2 129.0(3) . . ?
C5 C4 C3 116.4(3) . . ?
C5 C4 C10 122.6(3) . . ?
C3 C4 C10 121.0(3) . . ?
C6 C5 C4 123.7(4) . . ?
C6 C5 H5A 118.2 . . ?
C4 C5 H5A 118.2 . . ?
C5 C6 C7 118.3(3) . . ?
C5 C6 C14 121.3(4) . . ?
C7 C6 C14 120.4(4) . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C7 C8 C3 121.1(3) . . ?
C7 C8 C9 128.2(3) . . ?
C3 C8 C9 110.7(3) . . ?
N1 C9 C8 104.1(3) . . ?
N1 C9 C15 110.0(3) . . ?
C8 C9 C15 113.4(3) . . ?
N1 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C15 C9 H9A 109.7 . . ?
C11 C10 C4 127.3(3) . . ?
C11 C10 H10A 116.4 . . ?
C4 C10 H10A 116.4 . . ?
C10 C11 C12 122.6(4) . . ?
C10 C11 H11A 118.7 . . ?
C12 C11 H11A 118.7 . . ?
O4 C12 O5 123.0(4) . . ?
O4 C12 C11 125.7(3) . . ?
O5 C12 C11 111.3(4) . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C9 110.6(3) . . ?
C16 C15 H15A 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O6 C16 O7 124.1(4) . . ?
O6 C16 C15 124.3(5) . . ?
O7 C16 C15 111.6(4) . . ?
O7 C17 H17A 109.5 . . ?
O7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 S1 O3 C1 -135.3(4) . . . . ?
O2 S1 O3 C1 96.5(4) . . . . ?
N1 S1 O3 C1 -20.3(4) . . . . ?
O1 S1 N1 C2 116.5(3) . . . . ?
O2 S1 N1 C2 -108.7(3) . . . . ?
O3 S1 N1 C2 6.8(3) . . . . ?
O1 S1 N1 C9 -114.8(3) . . . . ?
O2 S1 N1 C9 20.0(3) . . . . ?
O3 S1 N1 C9 135.5(3) . . . . ?
S1 O3 C1 C2 25.7(5) . . . . ?
C9 N1 C2 C3 -5.4(3) . . . . ?
S1 N1 C2 C3 127.7(2) . . . . ?
C9 N1 C2 C1 -127.0(3) . . . . ?
S1 N1 C2 C1 6.2(3) . . . . ?
O3 C1 C2 N1 -18.2(4) . . . . ?
O3 C1 C2 C3 -132.4(4) . . . . ?
N1 C2 C3 C8 1.0(4) . . . . ?
C1 C2 C3 C8 116.4(3) . . . . ?
N1 C2 C3 C4 -176.3(3) . . . . ?
C1 C2 C3 C4 -60.8(5) . . . . ?
C8 C3 C4 C5 -0.5(5) . . . . ?
C2 C3 C4 C5 176.5(3) . . . . ?
C8 C3 C4 C10 -179.0(3) . . . . ?
C2 C3 C4 C10 -2.1(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C10 C4 C5 C6 177.7(3) . . . . ?
C4 C5 C6 C7 1.7(6) . . . . ?
C4 C5 C6 C14 -177.9(4) . . . . ?
C5 C6 C7 C8 -1.2(5) . . . . ?
C14 C6 C7 C8 178.4(4) . . . . ?
C6 C7 C8 C3 -0.1(5) . . . . ?
C6 C7 C8 C9 179.4(3) . . . . ?
C4 C3 C8 C7 1.0(5) . . . . ?
C2 C3 C8 C7 -176.5(3) . . . . ?
C4 C3 C8 C9 -178.6(3) . . . . ?
C2 C3 C8 C9 3.9(4) . . . . ?
C2 N1 C9 C8 7.6(4) . . . . ?
S1 N1 C9 C8 -120.8(3) . . . . ?
C2 N1 C9 C15 -114.2(3) . . . . ?
S1 N1 C9 C15 117.5(3) . . . . ?
C7 C8 C9 N1 173.5(3) . . . . ?
C3 C8 C9 N1 -7.0(4) . . . . ?
C7 C8 C9 C15 -67.1(5) . . . . ?
C3 C8 C9 C15 112.5(4) . . . . ?
C5 C4 C10 C11 -6.3(6) . . . . ?
C3 C4 C10 C11 172.1(3) . . . . ?
C4 C10 C11 C12 -179.9(3) . . . . ?
C13 O5 C12 O4 -1.0(6) . . . . ?
C13 O5 C12 C11 -179.8(3) . . . . ?
C10 C11 C12 O4 3.0(6) . . . . ?
C10 C11 C12 O5 -178.3(3) . . . . ?
N1 C9 C15 C16 -65.6(5) . . . . ?
C8 C9 C15 C16 178.3(4) . . . . ?
C17 O7 C16 O6 3.6(7) . . . . ?
C17 O7 C16 C15 -178.1(4) . . . . ?
C9 C15 C16 O6 -39.5(7) . . . . ?
C9 C15 C16 O7 142.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_20150720_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1432488'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        sulfamidate+acrylronitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 N2 O3 S'
_chemical_formula_weight         250.27

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.1628(2)
_cell_length_b                   8.1111(1)
_cell_length_c                   17.0276(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.533(1)
_cell_angle_gamma                90.00
_cell_volume                     1127.34(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    9128
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8685
_exptl_absorpt_correction_T_max  0.9559
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20136
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         28.30
_reflns_number_total             2800
_reflns_number_gt                2443
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0536P)²+0.2825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2800
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.32433(5) 0.36850(4) 0.19213(2) 0.04405(13) Uani 1 1 d . . .
O1 O 0.46780(16) 0.31311(16) 0.23076(9) 0.0703(4) Uani 1 1 d . . .
O2 O 0.22700(17) 0.49120(15) 0.22849(7) 0.0630(3) Uani 1 1 d . . .
O3 O 0.37334(14) 0.43329(14) 0.10823(7) 0.0534(3) Uani 1 1 d . . .
N1 N 0.20590(14) 0.21482(13) 0.16397(6) 0.0365(2) Uani 1 1 d . . .
N2 N 0.1589(3) 0.0342(3) 0.36405(9) 0.0800(5) Uani 1 1 d . . .
C1 C 0.2287(2) 0.41547(19) 0.05839(10) 0.0563(4) Uani 1 1 d . . .
H1B H 0.2589 0.4150 0.0034 0.068 Uiso 1 1 calc R . .
H1C H 0.1528 0.5055 0.0672 0.068 Uiso 1 1 calc R . .
C2 C 0.15076(18) 0.25008(17) 0.08131(8) 0.0407(3) Uani 1 1 d . . .
H2B H 0.0310 0.2575 0.0784 0.049 Uiso 1 1 calc R . .
C3 C 0.20985(17) 0.10303(17) 0.03637(8) 0.0384(3) Uani 1 1 d . . .
C4 C 0.2011(2) 0.0755(2) -0.04427(9) 0.0519(4) Uani 1 1 d . . .
H4A H 0.1536 0.1530 -0.0777 0.062 Uiso 1 1 calc R . .
C5 C 0.2646(2) -0.0696(2) -0.07338(10) 0.0587(4) Uani 1 1 d . . .
H5A H 0.2599 -0.0900 -0.1271 0.070 Uiso 1 1 calc R . .
C6 C 0.3351(2) -0.1850(2) -0.02394(11) 0.0580(4) Uani 1 1 d . . .
H6A H 0.3766 -0.2823 -0.0447 0.070 Uiso 1 1 calc R . .
C7 C 0.3448(2) -0.15755(18) 0.05633(10) 0.0491(4) Uani 1 1 d . . .
H7A H 0.3928 -0.2348 0.0897 0.059 Uiso 1 1 calc R . .
C8 C 0.28087(16) -0.01145(16) 0.08546(8) 0.0371(3) Uani 1 1 d . . .
C9 C 0.27681(16) 0.04486(15) 0.16943(7) 0.0365(3) Uani 1 1 d . . .
H9A H 0.3879 0.0488 0.1917 0.044 Uiso 1 1 calc R . .
C10 C 0.1666(2) -0.06505(18) 0.21964(8) 0.0456(3) Uani 1 1 d . . .
H10A H 0.0564 -0.0643 0.1978 0.055 Uiso 1 1 calc R . .
H10B H 0.2069 -0.1775 0.2179 0.055 Uiso 1 1 calc R . .
C11 C 0.1619(2) -0.0099(2) 0.30116(9) 0.0547(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4113(12) . ?
S1 O2 1.4192(12) . ?
S1 O3 1.5773(12) . ?
S1 N1 1.6461(11) . ?
O3 C1 1.455(2) . ?
N1 C9 1.4977(16) . ?
N1 C2 1.5011(16) . ?
N2 C11 1.129(2) . ?
C1 C2 1.537(2) . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.4993(19) . ?
C2 H2B 0.9800 . ?
C3 C8 1.3742(19) . ?
C3 C4 1.3922(19) . ?
C4 C5 1.380(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.386(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.3884(19) . ?
C7 H7A 0.9300 . ?
C8 C9 1.5016(18) . ?
C9 C10 1.5325(19) . ?
C9 H9A 0.9800 . ?
C10 C11 1.459(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
O1 S1 O2 119.04(8) . . ?
O1 S1 O3 108.17(8) . . ?
O2 S1 O3 108.01(7) . . ?
O1 S1 N1 112.16(7) . . ?
O2 S1 N1 109.18(7) . . ?
O3 S1 N1 98.14(6) . . ?
C1 O3 S1 106.50(10) . . ?
C9 N1 C2 110.24(10) . . ?
C9 N1 S1 116.96(8) . . ?
C2 N1 S1 107.40(9) . . ?
O3 C1 C2 105.91(12) . . ?
O3 C1 H1B 110.6 . . ?
C2 C1 H1B 110.6 . . ?
O3 C1 H1C 110.6 . . ?
C2 C1 H1C 110.6 . . ?
H1B C1 H1C 108.7 . . ?
C3 C2 N1 103.41(10) . . ?
C3 C2 C1 115.40(13) . . ?
N1 C2 C1 106.46(11) . . ?
C3 C2 H2B 110.4 . . ?
N1 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
C8 C3 C4 120.59(14) . . ?
C8 C3 C2 111.28(11) . . ?
C4 C3 C2 128.12(13) . . ?
C5 C4 C3 118.37(16) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
C4 C5 C6 121.00(15) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C5 C6 C7 120.77(15) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C6 C7 C8 118.12(15) . . ?
C6 C7 H7A 120.9 . . ?
C8 C7 H7A 120.9 . . ?
C3 C8 C7 121.15(13) . . ?
C3 C8 C9 111.15(11) . . ?
C7 C8 C9 127.70(13) . . ?
N1 C9 C8 103.46(10) . . ?
N1 C9 C10 109.98(11) . . ?
C8 C9 C10 111.87(11) . . ?
N1 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
C10 C9 H9A 110.4 . . ?
C11 C10 C9 111.91(12) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C10 179.35(19) . . ?

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
O1 S1 O3 C1 153.76(10) . . . . ?
O2 S1 O3 C1 -76.15(11) . . . . ?
N1 S1 O3 C1 37.15(10) . . . . ?
O1 S1 N1 C9 -10.53(13) . . . . ?
O2 S1 N1 C9 -144.69(10) . . . . ?
O3 S1 N1 C9 102.94(10) . . . . ?
O1 S1 N1 C2 -135.01(11) . . . . ?
O2 S1 N1 C2 90.82(10) . . . . ?
O3 S1 N1 C2 -21.54(10) . . . . ?
S1 O3 C1 C2 -39.86(14) . . . . ?
C9 N1 C2 C3 -6.53(14) . . . . ?
S1 N1 C2 C3 121.93(10) . . . . ?
C9 N1 C2 C1 -128.55(12) . . . . ?
S1 N1 C2 C1 -0.09(14) . . . . ?
O3 C1 C2 C3 -89.74(15) . . . . ?
O3 C1 C2 N1 24.34(16) . . . . ?
N1 C2 C3 C8 3.76(15) . . . . ?
C1 C2 C3 C8 119.59(14) . . . . ?
N1 C2 C3 C4 -175.60(14) . . . . ?
C1 C2 C3 C4 -59.78(19) . . . . ?
C8 C3 C4 C5 0.3(2) . . . . ?
C2 C3 C4 C5 179.65(14) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C4 C3 C8 C7 -0.4(2) . . . . ?
C2 C3 C8 C7 -179.78(12) . . . . ?
C4 C3 C8 C9 179.80(12) . . . . ?
C2 C3 C8 C9 0.38(16) . . . . ?
C6 C7 C8 C3 0.0(2) . . . . ?
C6 C7 C8 C9 179.81(14) . . . . ?
C2 N1 C9 C8 6.73(13) . . . . ?
S1 N1 C9 C8 -116.31(10) . . . . ?
C2 N1 C9 C10 -112.91(12) . . . . ?
S1 N1 C9 C10 124.05(10) . . . . ?
C3 C8 C9 N1 -4.36(14) . . . . ?
C7 C8 C9 N1 175.82(13) . . . . ?
C3 C8 C9 C10 113.98(13) . . . . ?
C7 C8 C9 C10 -65.84(18) . . . . ?
N1 C9 C10 C11 -65.30(16) . . . . ?
C8 C9 C10 C11 -179.68(13) . . . . ?
C9 C10 C11 N2 13(21) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_20151103lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1435134'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3a-methylacrylate
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O7 S'
_chemical_formula_weight         367.37

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   P2(1)

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

_cell_length_a                   6.1638(3)
_cell_length_b                   14.6526(7)
_cell_length_c                   9.1812(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.564(3)
_cell_angle_gamma                90.00
_cell_volume                     809.35(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5213
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.06

_exptl_crystal_description       block
_exptl_crystal_colour            silver
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9270
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14993
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         28.46
_reflns_number_total             4033
_reflns_number_gt                3631
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0628P)²+0.2179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_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   0.06(7)
_refine_ls_number_reflns         4033
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
S1 S 1.38588(9) 0.03762(4) 1.19509(6) 0.02490(14) Uani 1 1 d . . .
O1 O 1.5748(3) 0.07692(15) 1.1548(2) 0.0380(5) Uani 1 1 d . . .
O2 O 1.4326(3) -0.02678(16) 1.3155(2) 0.0430(5) Uani 1 1 d . . .
O3 O 1.2217(3) 0.10883(14) 1.23690(19) 0.0337(4) Uani 1 1 d . . .
O4 O 1.3018(3) -0.22185(13) 0.6756(2) 0.0366(4) Uani 1 1 d . . .
O5 O 1.5796(3) -0.12416(12) 0.76535(18) 0.0278(4) Uani 1 1 d . . .
O6 O 0.2968(3) 0.26752(13) 0.88800(18) 0.0295(4) Uani 1 1 d . . .
O7 O 0.1710(3) 0.30325(12) 0.64620(18) 0.0281(4) Uani 1 1 d . . .
N1 N 1.2132(3) -0.00461(13) 1.0484(2) 0.0201(4) Uani 1 1 d . . .
C1 C 1.3029(4) -0.03009(15) 0.9158(2) 0.0204(4) Uani 1 1 d . . .
H1B H 1.4596 -0.0083 0.9282 0.024 Uiso 1 1 calc R . .
C2 C 1.1527(4) 0.02074(14) 0.7909(2) 0.0191(4) Uani 1 1 d . . .
C3 C 1.1665(4) 0.02407(16) 0.6415(2) 0.0236(5) Uani 1 1 d . . .
H3A H 1.2841 -0.0056 0.6084 0.028 Uiso 1 1 calc R . .
C4 C 1.0046(5) 0.07169(17) 0.5426(3) 0.0285(5) Uani 1 1 d . . .
H4A H 1.0104 0.0741 0.4402 0.034 Uiso 1 1 calc R . .
C5 C 0.8346(4) 0.11574(17) 0.5903(3) 0.0270(5) Uani 1 1 d . . .
H5A H 0.7255 0.1476 0.5195 0.032 Uiso 1 1 calc R . .
C6 C 0.8183(4) 0.11475(15) 0.7406(2) 0.0216(4) Uani 1 1 d . . .
C7 C 0.9834(3) 0.06592(15) 0.8407(2) 0.0189(4) Uani 1 1 d . . .
C8 C 1.0108(3) 0.05415(15) 1.0066(2) 0.0198(4) Uani 1 1 d . . .
H8A H 0.8786 0.0225 1.0298 0.024 Uiso 1 1 calc R . .
C9 C 1.0653(4) 0.14095(16) 1.1011(2) 0.0244(5) Uani 1 1 d . . .
H9A H 1.1355 0.1875 1.0482 0.029 Uiso 1 1 calc R . .
H9B H 0.9297 0.1672 1.1258 0.029 Uiso 1 1 calc R . .
C10 C 1.6814(4) -0.14624(19) 0.6413(2) 0.0300(5) Uani 1 1 d . . .
H10A H 1.8206 -0.1122 0.6511 0.045 Uiso 1 1 calc R . .
H10B H 1.5798 -0.1296 0.5473 0.045 Uiso 1 1 calc R . .
H10C H 1.7123 -0.2119 0.6416 0.045 Uiso 1 1 calc R . .
C11 C 1.3869(4) -0.16608(15) 0.7669(3) 0.0251(5) Uani 1 1 d . . .
C12 C 1.2918(4) -0.13377(16) 0.8957(2) 0.0244(5) Uani 1 1 d . . .
H12A H 1.3743 -0.1630 0.9885 0.029 Uiso 1 1 calc R . .
H12B H 1.1348 -0.1535 0.8795 0.029 Uiso 1 1 calc R . .
C13 C 0.6404(4) 0.16400(16) 0.7922(2) 0.0230(4) Uani 1 1 d . . .
H13A H 0.6370 0.1603 0.8950 0.028 Uiso 1 1 calc R . .
C14 C 0.4850(4) 0.21317(17) 0.7037(3) 0.0269(5) Uani 1 1 d . . .
H14A H 0.4855 0.2166 0.6005 0.032 Uiso 1 1 calc R . .
C15 C 0.3127(4) 0.26224(16) 0.7592(3) 0.0237(5) Uani 1 1 d . . .
C16 C -0.0018(4) 0.35753(19) 0.6853(3) 0.0302(5) Uani 1 1 d . . .
H16A H -0.0943 0.3840 0.5948 0.045 Uiso 1 1 calc R . .
H16B H 0.0648 0.4066 0.7530 0.045 Uiso 1 1 calc R . .
H16C H -0.0939 0.3190 0.7349 0.045 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
S1 O1 1.4185(17) . ?
S1 O2 1.435(2) . ?
S1 O3 1.5586(19) . ?
S1 N1 1.6452(19) . ?
O3 C9 1.477(3) . ?
O4 C11 1.206(3) . ?
O5 C11 1.340(3) . ?
O5 C10 1.452(3) . ?
O6 C15 1.210(3) . ?
O7 C15 1.344(3) . ?
O7 C16 1.436(3) . ?
N1 C1 1.490(3) . ?
N1 C8 1.495(3) . ?
C1 C2 1.505(3) . ?
C1 C12 1.530(3) . ?
C1 H1B 1.0000 . ?
C2 C7 1.394(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.383(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.409(3) . ?
C6 C13 1.474(3) . ?
C7 C8 1.505(3) . ?
C8 C9 1.535(3) . ?
C8 H8A 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.506(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.326(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.463(3) . ?
C14 H14A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 115.44(12) . . ?
O1 S1 O3 113.98(12) . . ?
O2 S1 O3 106.42(12) . . ?
O1 S1 N1 111.16(10) . . ?
O2 S1 N1 111.67(12) . . ?
O3 S1 N1 96.56(9) . . ?
C9 O3 S1 110.17(14) . . ?
C11 O5 C10 116.20(19) . . ?
C15 O7 C16 116.58(18) . . ?
C1 N1 C8 111.82(17) . . ?
C1 N1 S1 118.31(14) . . ?
C8 N1 S1 110.39(14) . . ?
N1 C1 C2 102.84(17) . . ?
N1 C1 C12 109.42(17) . . ?
C2 C1 C12 113.31(18) . . ?
N1 C1 H1B 110.3 . . ?
C2 C1 H1B 110.3 . . ?
C12 C1 H1B 110.3 . . ?
C7 C2 C3 121.1(2) . . ?
C7 C2 C1 111.44(18) . . ?
C3 C2 C1 127.4(2) . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4A 119.4 . . ?
C3 C4 H4A 119.4 . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C7 116.7(2) . . ?
C5 C6 C13 121.8(2) . . ?
C7 C6 C13 121.41(19) . . ?
C2 C7 C6 120.87(19) . . ?
C2 C7 C8 110.51(18) . . ?
C6 C7 C8 128.62(19) . . ?
N1 C8 C7 103.25(16) . . ?
N1 C8 C9 105.33(17) . . ?
C7 C8 C9 116.08(18) . . ?
N1 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O3 C9 C8 103.62(18) . . ?
O3 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
O3 C9 H9B 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O5 123.8(2) . . ?
O4 C11 C12 125.0(2) . . ?
O5 C11 C12 111.20(19) . . ?
C11 C12 C1 113.08(19) . . ?
C11 C12 H12A 109.0 . . ?
C1 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C1 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C6 123.9(2) . . ?
C14 C13 H13A 118.1 . . ?
C6 C13 H13A 118.1 . . ?
C13 C14 C15 122.4(2) . . ?
C13 C14 H14A 118.8 . . ?
C15 C14 H14A 118.8 . . ?
O6 C15 O7 123.3(2) . . ?
O6 C15 C14 126.2(2) . . ?
O7 C15 C14 110.5(2) . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 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
O1 S1 O3 C9 85.49(18) . . . . ?
O2 S1 O3 C9 -146.11(16) . . . . ?
N1 S1 O3 C9 -31.19(17) . . . . ?
O1 S1 N1 C1 23.3(2) . . . . ?
O2 S1 N1 C1 -107.21(18) . . . . ?
O3 S1 N1 C1 142.19(16) . . . . ?
O1 S1 N1 C8 -107.30(16) . . . . ?
O2 S1 N1 C8 122.20(15) . . . . ?
O3 S1 N1 C8 11.60(16) . . . . ?
C8 N1 C1 C2 3.2(2) . . . . ?
S1 N1 C1 C2 -126.74(16) . . . . ?
C8 N1 C1 C12 -117.50(19) . . . . ?
S1 N1 C1 C12 112.55(17) . . . . ?
N1 C1 C2 C7 -3.9(2) . . . . ?
C12 C1 C2 C7 114.1(2) . . . . ?
N1 C1 C2 C3 177.5(2) . . . . ?
C12 C1 C2 C3 -64.5(3) . . . . ?
C7 C2 C3 C4 -1.5(3) . . . . ?
C1 C2 C3 C4 177.0(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C4 C5 C6 C13 178.2(2) . . . . ?
C3 C2 C7 C6 1.4(3) . . . . ?
C1 C2 C7 C6 -177.36(19) . . . . ?
C3 C2 C7 C8 -178.1(2) . . . . ?
C1 C2 C7 C8 3.2(2) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C13 C6 C7 C2 -179.0(2) . . . . ?
C5 C6 C7 C8 179.0(2) . . . . ?
C13 C6 C7 C8 0.3(3) . . . . ?
C1 N1 C8 C7 -1.5(2) . . . . ?
S1 N1 C8 C7 132.43(15) . . . . ?
C1 N1 C8 C9 -123.70(18) . . . . ?
S1 N1 C8 C9 10.24(19) . . . . ?
C2 C7 C8 N1 -1.0(2) . . . . ?
C6 C7 C8 N1 179.6(2) . . . . ?
C2 C7 C8 C9 113.7(2) . . . . ?
C6 C7 C8 C9 -65.8(3) . . . . ?
S1 O3 C9 C8 39.8(2) . . . . ?
N1 C8 C9 O3 -29.4(2) . . . . ?
C7 C8 C9 O3 -142.86(17) . . . . ?
C10 O5 C11 O4 2.7(3) . . . . ?
C10 O5 C11 C12 -176.81(19) . . . . ?
O4 C11 C12 C1 -135.0(2) . . . . ?
O5 C11 C12 C1 44.5(2) . . . . ?
N1 C1 C12 C11 -177.96(18) . . . . ?
C2 C1 C12 C11 67.9(2) . . . . ?
C5 C6 C13 C14 -0.7(4) . . . . ?
C7 C6 C13 C14 177.9(2) . . . . ?
C6 C13 C14 C15 -179.1(2) . . . . ?
C16 O7 C15 O6 1.8(3) . . . . ?
C16 O7 C15 C14 -177.3(2) . . . . ?
C13 C14 C15 O6 3.5(4) . . . . ?
C13 C14 C15 O7 -177.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.056
