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

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

data_xb7926_0m
_database_code_depnum_ccdc_archive 'CCDC 1046800'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O4 S'
_chemical_formula_weight         358.40

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   8.8040(16)
_cell_length_b                   10.9952(19)
_cell_length_c                   18.299(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.334(3)
_cell_angle_gamma                90.00
_cell_volume                     1756.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2349
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9292
_exptl_absorpt_correction_T_max  0.9532
_exptl_absorpt_process_details   STABAS

_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            8577
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3133
_reflns_number_gt                2244
_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)+(0.0444P)²+0.2764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.59685(6) 0.90700(5) 0.22428(3) 0.06342(19) Uani 1 1 d . . .
N1 N 0.64645(19) 0.79485(15) 0.17178(9) 0.0632(5) Uani 1 1 d . . .
N2 N 0.3020(2) 0.93987(17) 0.18512(9) 0.0697(5) Uani 1 1 d . . .
O1 O 0.91289(16) 1.20992(13) -0.03018(8) 0.0723(4) Uani 1 1 d . . .
O2 O 0.9703(2) 1.14428(16) 0.08572(9) 0.0899(5) Uani 1 1 d . . .
O3 O 0.61115(17) 1.01788(12) 0.18547(7) 0.0704(4) Uani 1 1 d . . .
O4 O 0.68361(19) 0.88823(15) 0.29489(8) 0.0888(5) Uani 1 1 d . . .
C1 C 1.0237(4) 1.3766(3) -0.08515(18) 0.1251(12) Uani 1 1 d . . .
H1A H 1.0536 1.3227 -0.1221 0.188 Uiso 1 1 calc R . .
H1B H 1.0958 1.4423 -0.0773 0.188 Uiso 1 1 calc R . .
H1C H 0.9236 1.4086 -0.1013 0.188 Uiso 1 1 calc R . .
C2 C 1.0206(3) 1.3090(2) -0.01544(16) 0.0891(8) Uani 1 1 d . . .
H2A H 1.1217 1.2776 0.0020 0.107 Uiso 1 1 calc R . .
H2B H 0.9889 1.3622 0.0221 0.107 Uiso 1 1 calc R . .
C3 C 0.8974(2) 1.13427(19) 0.02591(13) 0.0612(5) Uani 1 1 d . . .
C4 C 0.7814(2) 1.04168(18) 0.00485(10) 0.0567(5) Uani 1 1 d . . .
H4 H 0.7325 1.0401 -0.0433 0.068 Uiso 1 1 calc R . .
C5 C 0.7445(2) 0.96062(18) 0.05203(10) 0.0544(5) Uani 1 1 d . . .
H5 H 0.7971 0.9645 0.0994 0.065 Uiso 1 1 calc R . .
C6 C 0.6292(2) 0.86440(17) 0.03811(11) 0.0528(5) Uani 1 1 d . . .
C7 C 0.5601(2) 0.83827(19) -0.03331(11) 0.0603(5) Uani 1 1 d . . .
H7 H 0.5807 0.8881 -0.0719 0.072 Uiso 1 1 calc R . .
C8 C 0.4623(2) 0.7405(2) -0.04808(13) 0.0710(6) Uani 1 1 d . . .
H8 H 0.4165 0.7266 -0.0960 0.085 Uiso 1 1 calc R . .
C9 C 0.4320(3) 0.6637(2) 0.00758(15) 0.0767(7) Uani 1 1 d . . .
H9 H 0.3692 0.5963 -0.0029 0.092 Uiso 1 1 calc R . .
C10 C 0.4954(3) 0.68730(19) 0.07882(13) 0.0678(6) Uani 1 1 d . . .
C11 C 0.5880(2) 0.78885(18) 0.09410(11) 0.0560(5) Uani 1 1 d . . .
C12 C 0.6222(3) 0.6681(2) 0.19993(14) 0.0862(8) Uani 1 1 d . . .
H12A H 0.5989 0.6708 0.2503 0.103 Uiso 1 1 calc R . .
H12B H 0.7130 0.6187 0.1982 0.103 Uiso 1 1 calc R . .
C13 C 0.4877(3) 0.6169(2) 0.14879(15) 0.0919(8) Uani 1 1 d . . .
H13A H 0.4997 0.5304 0.1410 0.110 Uiso 1 1 calc R . .
H13B H 0.3916 0.6312 0.1681 0.110 Uiso 1 1 calc R . .
C14 C 0.4000(2) 0.88557(18) 0.23511(10) 0.0569(5) Uani 1 1 d . . .
C15 C 0.1537(3) 0.9230(3) 0.19127(14) 0.0869(7) Uani 1 1 d . . .
H15 H 0.0820 0.9613 0.1572 0.104 Uiso 1 1 calc R . .
C16 C 0.1010(3) 0.8533(3) 0.24419(16) 0.0934(8) Uani 1 1 d . . .
H16 H -0.0035 0.8443 0.2460 0.112 Uiso 1 1 calc R . .
C17 C 0.2053(4) 0.7970(3) 0.29438(16) 0.1029(9) Uani 1 1 d . . .
H17 H 0.1729 0.7471 0.3304 0.123 Uiso 1 1 calc R . .
C18 C 0.3596(3) 0.8149(2) 0.29117(12) 0.0859(7) Uani 1 1 d . . .
H18 H 0.4335 0.7801 0.3258 0.103 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 O3 1.4245(14) . ?
S1 O4 1.4295(14) . ?
S1 N1 1.6557(18) . ?
S1 C14 1.785(2) . ?
N1 C11 1.450(2) . ?
N1 C12 1.510(3) . ?
N2 C14 1.318(2) . ?
N2 C15 1.338(3) . ?
O1 C3 1.342(2) . ?
O1 C2 1.447(3) . ?
O2 C3 1.201(2) . ?
C1 C2 1.480(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.458(3) . ?
C4 C5 1.310(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.466(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(3) . ?
C6 C11 1.402(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(3) . ?
C10 C13 1.505(3) . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C18 1.370(3) . ?
C15 C16 1.362(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.361(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 120.21(10) . . ?
O3 S1 N1 107.54(9) . . ?
O4 S1 N1 105.47(9) . . ?
O3 S1 C14 108.50(9) . . ?
O4 S1 C14 107.15(10) . . ?
N1 S1 C14 107.33(9) . . ?
C11 N1 C12 104.16(17) . . ?
C11 N1 S1 121.05(12) . . ?
C12 N1 S1 115.47(14) . . ?
C14 N2 C15 116.0(2) . . ?
C3 O1 C2 116.89(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 107.5(2) . . ?
O1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 123.1(2) . . ?
O2 C3 C4 125.4(2) . . ?
O1 C3 C4 111.52(18) . . ?
C5 C4 C3 121.66(19) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 126.94(18) . . ?
C4 C5 H5 116.5 . . ?
C6 C5 H5 116.5 . . ?
C7 C6 C11 116.03(18) . . ?
C7 C6 C5 121.29(18) . . ?
C11 C6 C5 122.58(18) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 C13 130.7(2) . . ?
C11 C10 C13 109.3(2) . . ?
C10 C11 C6 121.92(19) . . ?
C10 C11 N1 111.06(18) . . ?
C6 C11 N1 126.65(18) . . ?
N1 C12 C13 105.34(18) . . ?
N1 C12 H12A 110.7 . . ?
C13 C12 H12A 110.7 . . ?
N1 C12 H12B 110.7 . . ?
C13 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C10 C13 C12 102.5(2) . . ?
C10 C13 H13A 111.3 . . ?
C12 C13 H13A 111.3 . . ?
C10 C13 H13B 111.3 . . ?
C12 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
N2 C14 C18 124.6(2) . . ?
N2 C14 S1 114.97(15) . . ?
C18 C14 S1 120.43(17) . . ?
N2 C15 C16 124.2(2) . . ?
N2 C15 H15 117.9 . . ?
C16 C15 H15 117.9 . . ?
C17 C16 C15 118.3(3) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C16 C17 C18 119.3(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C14 C18 C17 117.6(2) . . ?
C14 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?

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
O3 S1 N1 C11 -46.49(17) . . . . ?
O4 S1 N1 C11 -175.91(15) . . . . ?
C14 S1 N1 C11 70.07(17) . . . . ?
O3 S1 N1 C12 -173.58(15) . . . . ?
O4 S1 N1 C12 57.00(18) . . . . ?
C14 S1 N1 C12 -57.01(17) . . . . ?
C3 O1 C2 C1 177.6(2) . . . . ?
C2 O1 C3 O2 -1.6(3) . . . . ?
C2 O1 C3 C4 177.70(17) . . . . ?
O2 C3 C4 C5 1.4(3) . . . . ?
O1 C3 C4 C5 -177.87(18) . . . . ?
C3 C4 C5 C6 179.15(18) . . . . ?
C4 C5 C6 C7 9.8(3) . . . . ?
C4 C5 C6 C11 -174.00(19) . . . . ?
C11 C6 C7 C8 -2.7(3) . . . . ?
C5 C6 C7 C8 173.75(18) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C10 2.4(3) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C8 C9 C10 C13 -177.0(2) . . . . ?
C9 C10 C11 C6 -4.9(3) . . . . ?
C13 C10 C11 C6 173.16(18) . . . . ?
C9 C10 C11 N1 -178.32(18) . . . . ?
C13 C10 C11 N1 -0.3(2) . . . . ?
C7 C6 C11 C10 5.8(3) . . . . ?
C5 C6 C11 C10 -170.59(18) . . . . ?
C7 C6 C11 N1 178.13(17) . . . . ?
C5 C6 C11 N1 1.8(3) . . . . ?
C12 N1 C11 C10 17.0(2) . . . . ?
S1 N1 C11 C10 -115.04(17) . . . . ?
C12 N1 C11 C6 -156.04(19) . . . . ?
S1 N1 C11 C6 71.9(2) . . . . ?
C11 N1 C12 C13 -26.7(2) . . . . ?
S1 N1 C12 C13 108.52(19) . . . . ?
C9 C10 C13 C12 161.4(2) . . . . ?
C11 C10 C13 C12 -16.4(2) . . . . ?
N1 C12 C13 C10 26.1(2) . . . . ?
C15 N2 C14 C18 0.1(3) . . . . ?
C15 N2 C14 S1 178.67(16) . . . . ?
O3 S1 C14 N2 25.49(18) . . . . ?
O4 S1 C14 N2 156.67(15) . . . . ?
N1 S1 C14 N2 -90.45(17) . . . . ?
O3 S1 C14 C18 -155.89(18) . . . . ?
O4 S1 C14 C18 -24.7(2) . . . . ?
N1 S1 C14 C18 88.18(19) . . . . ?
C14 N2 C15 C16 -1.0(4) . . . . ?
N2 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C18 1.7(4) . . . . ?
N2 C14 C18 C17 1.6(4) . . . . ?
S1 C14 C18 C17 -176.88(19) . . . . ?
C16 C17 C18 C14 -2.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_xb7209_0m
_database_code_depnum_ccdc_archive 'CCDC 1046801'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O4 S'
_chemical_formula_weight         358.40

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

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

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

_cell_length_a                   9.0332(18)
_cell_length_b                   10.971(2)
_cell_length_c                   17.316(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1716.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4814
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.41

_exptl_crystal_description       colourless
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9259
_exptl_absorpt_correction_T_max  0.9478
_exptl_absorpt_process_details   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            8397
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.09
_reflns_number_total             3057
_reflns_number_gt                2849
_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)+(0.0396P)²+0.1155P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.04(6)
_refine_ls_number_reflns         3057
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.86694(5) 0.41133(4) 0.88253(2) 0.03977(13) Uani 1 1 d . . .
N1 N 0.85827(16) 0.34320(13) 0.79794(8) 0.0379(3) Uani 1 1 d . . .
N2 N 1.1040(2) 0.54328(15) 0.85638(9) 0.0492(4) Uani 1 1 d . . .
O1 O 0.78165(15) 0.52015(13) 0.87809(8) 0.0519(4) Uani 1 1 d . . .
O2 O 0.83100(17) 0.32138(14) 0.93855(8) 0.0567(4) Uani 1 1 d . . .
O3 O 0.38041(17) 0.38117(13) 0.57624(8) 0.0571(4) Uani 1 1 d . . .
O4 O 0.50833(19) 0.28403(14) 0.66697(11) 0.0709(5) Uani 1 1 d . . .
C1 C 1.0571(2) 0.44868(17) 0.89678(10) 0.0393(4) Uani 1 1 d . . .
C2 C 1.1461(2) 0.37678(19) 0.94248(11) 0.0509(5) Uani 1 1 d . . .
H2 H 1.1077 0.3116 0.9704 0.061 Uiso 1 1 calc R . .
C3 C 1.2948(2) 0.4055(2) 0.94517(12) 0.0594(6) Uani 1 1 d . . .
H3 H 1.3593 0.3592 0.9751 0.071 Uiso 1 1 calc R . .
C4 C 1.3465(3) 0.5021(2) 0.90370(12) 0.0613(6) Uani 1 1 d . . .
H4 H 1.4465 0.5223 0.9045 0.074 Uiso 1 1 calc R . .
C5 C 1.2483(2) 0.5690(2) 0.86087(12) 0.0582(6) Uani 1 1 d . . .
H5 H 1.2839 0.6358 0.8335 0.070 Uiso 1 1 calc R . .
C6 C 0.9687(2) 0.24334(17) 0.78672(11) 0.0464(5) Uani 1 1 d . . .
H6A H 0.9209 0.1702 0.7676 0.056 Uiso 1 1 calc R . .
H6B H 1.0184 0.2244 0.8349 0.056 Uiso 1 1 calc R . .
C7 C 1.0789(2) 0.29282(19) 0.72735(12) 0.0510(5) Uani 1 1 d . . .
H7A H 1.1630 0.3311 0.7523 0.061 Uiso 1 1 calc R . .
H7B H 1.1138 0.2289 0.6932 0.061 Uiso 1 1 calc R . .
C8 C 0.98709(19) 0.38417(18) 0.68466(10) 0.0403(4) Uani 1 1 d . . .
C9 C 1.0069(2) 0.43424(19) 0.61197(11) 0.0482(5) Uani 1 1 d . . .
H9 H 1.0915 0.4172 0.5834 0.058 Uiso 1 1 calc R . .
C10 C 0.8984(2) 0.5099(2) 0.58292(11) 0.0489(5) Uani 1 1 d . . .
H10 H 0.9109 0.5451 0.5345 0.059 Uiso 1 1 calc R . .
C11 C 0.7724(2) 0.53386(18) 0.62425(11) 0.0450(4) Uani 1 1 d . . .
H11 H 0.7008 0.5844 0.6027 0.054 Uiso 1 1 calc R . .
C12 C 0.74788(19) 0.48503(17) 0.69757(10) 0.0375(4) Uani 1 1 d . . .
C13 C 0.86077(17) 0.41225(15) 0.72672(9) 0.0339(4) Uani 1 1 d . . .
C14 C 0.59995(19) 0.50250(19) 0.73690(11) 0.0446(4) Uani 1 1 d . . .
H14A H 0.5867 0.4397 0.7757 0.054 Uiso 1 1 calc R . .
H14B H 0.5987 0.5809 0.7628 0.054 Uiso 1 1 calc R . .
C15 C 0.4748(2) 0.49679(18) 0.68007(11) 0.0426(4) Uani 1 1 d . . .
C16 C 0.45706(19) 0.37648(18) 0.64207(12) 0.0441(5) Uani 1 1 d . . .
C17 C 0.3646(3) 0.2680(2) 0.53528(14) 0.0739(7) Uani 1 1 d . . .
H17A H 0.4601 0.2404 0.5184 0.111 Uiso 1 1 calc R . .
H17B H 0.3017 0.2800 0.4912 0.111 Uiso 1 1 calc R . .
H17C H 0.3214 0.2081 0.5688 0.111 Uiso 1 1 calc R . .
C18 C 0.3853(2) 0.5887(2) 0.66469(13) 0.0586(5) Uani 1 1 d . . .
H18A H 0.3088 0.5790 0.6293 0.070 Uiso 1 1 calc R . .
H18B H 0.3987 0.6633 0.6893 0.070 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 1.4214(14) . ?
S1 O1 1.4229(14) . ?
S1 N1 1.6464(15) . ?
S1 C1 1.7831(19) . ?
N1 C13 1.448(2) . ?
N1 C6 1.495(2) . ?
N2 C1 1.321(2) . ?
N2 C5 1.336(3) . ?
O3 C16 1.335(2) . ?
O3 C17 1.437(3) . ?
O4 C16 1.195(2) . ?
C1 C2 1.376(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.530(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.496(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.385(3) . ?
C8 C13 1.388(2) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.396(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(2) . ?
C12 C14 1.512(2) . ?
C14 C15 1.500(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C18 1.320(3) . ?
C15 C16 1.483(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.72(9) . . ?
O2 S1 N1 106.33(9) . . ?
O1 S1 N1 107.88(8) . . ?
O2 S1 C1 106.57(9) . . ?
O1 S1 C1 109.65(9) . . ?
N1 S1 C1 105.86(8) . . ?
C13 N1 C6 105.22(13) . . ?
C13 N1 S1 121.31(11) . . ?
C6 N1 S1 114.62(12) . . ?
C1 N2 C5 116.60(18) . . ?
C16 O3 C17 116.10(17) . . ?
N2 C1 C2 124.56(18) . . ?
N2 C1 S1 114.58(14) . . ?
C2 C1 S1 120.70(15) . . ?
C1 C2 C3 117.2(2) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N2 C5 C4 123.4(2) . . ?
N2 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
N1 C6 C7 105.15(15) . . ?
N1 C6 H6A 110.7 . . ?
C7 C6 H6A 110.7 . . ?
N1 C6 H6B 110.7 . . ?
C7 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C8 C7 C6 102.09(15) . . ?
C8 C7 H7A 111.4 . . ?
C6 C7 H7A 111.4 . . ?
C8 C7 H7B 111.4 . . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.2 . . ?
C9 C8 C13 119.67(17) . . ?
C9 C8 C7 130.03(17) . . ?
C13 C8 C7 110.18(16) . . ?
C10 C9 C8 118.57(17) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 121.02(18) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 122.25(18) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 115.73(16) . . ?
C13 C12 C14 123.89(15) . . ?
C11 C12 C14 120.10(16) . . ?
C8 C13 C12 122.68(16) . . ?
C8 C13 N1 110.10(15) . . ?
C12 C13 N1 126.76(15) . . ?
C15 C14 C12 111.43(15) . . ?
C15 C14 H14A 109.3 . . ?
C12 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C12 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C18 C15 C16 121.64(18) . . ?
C18 C15 C14 124.19(19) . . ?
C16 C15 C14 114.16(16) . . ?
O4 C16 O3 122.8(2) . . ?
O4 C16 C15 123.58(18) . . ?
O3 C16 C15 113.61(16) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 120.0 . . ?
C15 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?

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 C13 168.09(13) . . . . ?
O1 S1 N1 C13 38.50(15) . . . . ?
C1 S1 N1 C13 -78.82(14) . . . . ?
O2 S1 N1 C6 -63.82(14) . . . . ?
O1 S1 N1 C6 166.59(13) . . . . ?
C1 S1 N1 C6 49.27(14) . . . . ?
C5 N2 C1 C2 0.2(3) . . . . ?
C5 N2 C1 S1 -175.21(16) . . . . ?
O2 S1 C1 N2 -171.16(14) . . . . ?
O1 S1 C1 N2 -40.20(16) . . . . ?
N1 S1 C1 N2 75.92(15) . . . . ?
O2 S1 C1 C2 13.20(19) . . . . ?
O1 S1 C1 C2 144.15(16) . . . . ?
N1 S1 C1 C2 -99.72(16) . . . . ?
N2 C1 C2 C3 -0.8(3) . . . . ?
S1 C1 C2 C3 174.40(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C1 N2 C5 C4 0.8(3) . . . . ?
C3 C4 C5 N2 -1.2(4) . . . . ?
C13 N1 C6 C7 26.05(18) . . . . ?
S1 N1 C6 C7 -109.78(15) . . . . ?
N1 C6 C7 C8 -25.55(18) . . . . ?
C6 C7 C8 C9 -159.36(19) . . . . ?
C6 C7 C8 C13 16.43(19) . . . . ?
C13 C8 C9 C10 -0.9(3) . . . . ?
C7 C8 C9 C10 174.56(19) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C10 C11 C12 C14 -173.01(19) . . . . ?
C9 C8 C13 C12 3.1(3) . . . . ?
C7 C8 C13 C12 -173.22(16) . . . . ?
C9 C8 C13 N1 175.81(15) . . . . ?
C7 C8 C13 N1 -0.5(2) . . . . ?
C11 C12 C13 C8 -3.1(3) . . . . ?
C14 C12 C13 C8 170.81(17) . . . . ?
C11 C12 C13 N1 -174.61(16) . . . . ?
C14 C12 C13 N1 -0.7(3) . . . . ?
C6 N1 C13 C8 -16.29(18) . . . . ?
S1 N1 C13 C8 115.85(15) . . . . ?
C6 N1 C13 C12 156.07(17) . . . . ?
S1 N1 C13 C12 -71.8(2) . . . . ?
C13 C12 C14 C15 -136.81(19) . . . . ?
C11 C12 C14 C15 36.9(2) . . . . ?
C12 C14 C15 C18 -116.4(2) . . . . ?
C12 C14 C15 C16 64.4(2) . . . . ?
C17 O3 C16 O4 -1.2(3) . . . . ?
C17 O3 C16 C15 177.67(19) . . . . ?
C18 C15 C16 O4 -160.4(2) . . . . ?
C14 C15 C16 O4 18.8(3) . . . . ?
C18 C15 C16 O3 20.7(3) . . . . ?
C14 C15 C16 O3 -160.00(16) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.034
