# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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

data_1_1099rd24_RAD212
_database_code_depnum_ccdc_archive 'CCDC 998930'
_audit_update_record             
;
2014-04-23 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            'Thiaplakortone A hydrochoride dihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N3 O4 S, Cl, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H16 Cl N3 O6 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         365.80
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
Cl Cl 0.1484 0.1585 ' 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'

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z

_cell_length_a                   14.5655(5)
_cell_length_b                   8.3351(3)
_cell_length_c                   26.0998(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3168.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    223.1(3)
_cell_measurement_reflns_used    2695
_cell_measurement_theta_min      3.6560
_cell_measurement_theta_max      31.9850

_exptl_crystal_description       plate
_exptl_crystal_colour            red

_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.407
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent, 2012),
;
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.960

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

# 7. EXPERIMENTAL DATA

_diffrn_ambient_temperature      223.1(3)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measurement_method       'ω scans'

# number of measured reflections (redundant set)
_diffrn_reflns_number            8729
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3640
# number of observed reflections (> n sig(I))
_reflns_number_gt                2950
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlis Pro(Oxford Diffraction, 2012)'
_computing_cell_refinement       'CrysAlis Pro'
_computing_data_reduction        'CrysAlis Pro'
_computing_structure_refinement  
'TeXSan (Molecular Structure Corporation, 2001), SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009), Westrip, 2010)'


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

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0474P)²+2.2268P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none

_refine_ls_number_reflns         3640
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.062

#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S Uani 0.12253(4) 0.29025(7) 0.36244(2) 1.000 0.0229(2) d . . .
O5 O Uani 0.46421(11) 0.2804(2) 0.32157(7) 1.000 0.0287(5) d . . .
O9 O Uani 0.11974(11) 0.1252(2) 0.26285(7) 1.000 0.0305(5) d . . .
O11 O Uani 0.07246(12) 0.1507(2) 0.37779(8) 1.000 0.0380(6) d . . .
O12 O Uani 0.06830(12) 0.4090(2) 0.33612(7) 1.000 0.0351(6) d . . .
N4 N Uani 0.32683(13) 0.3471(3) 0.38450(8) 1.000 0.0272(6) d . . .
N6 N Uani 0.42399(12) 0.1298(2) 0.22058(8) 1.000 0.0246(6) d . . .
N83 N Uani 0.07399(13) 0.0679(2) 0.10848(7) 1.000 0.0257(6) d . . .
C2 C Uani 0.17385(19) 0.3774(4) 0.41442(10) 1.000 0.0351(8) d . . .
C3 C Uani 0.26397(19) 0.3954(3) 0.41970(9) 1.000 0.0331(8) d . . .
C4A C Uani 0.30508(15) 0.2787(3) 0.33981(8) 1.000 0.0203(6) d . . .
C5 C Uani 0.38793(14) 0.2454(3) 0.30620(9) 1.000 0.0205(6) d . . .
C5A C Uani 0.36551(15) 0.1743(3) 0.25798(9) 1.000 0.0201(6) d . . .
C7 C Uani 0.37622(16) 0.0614(3) 0.18207(9) 1.000 0.0239(7) d . . .
C8 C Uani 0.28385(15) 0.0594(3) 0.19423(9) 1.000 0.0211(6) d . . .
C8A C Uani 0.27707(14) 0.1319(3) 0.24294(8) 1.000 0.0194(6) d . . .
C9 C Uani 0.19802(15) 0.1630(3) 0.27529(9) 1.000 0.0204(6) d . . .
C9A C Uani 0.21708(14) 0.2420(3) 0.32479(9) 1.000 0.0202(6) d . . .
C81 C Uani 0.20668(15) -0.0033(3) 0.16217(9) 1.000 0.0228(6) d . . .
C82 C Uani 0.15488(16) 0.1314(3) 0.13623(9) 1.000 0.0244(7) d . . .
Cl Cl Uani 0.15353(6) -0.15334(10) 0.02332(3) 1.000 0.0504(3) d . . .
O1 O Uani 0.01112(13) -0.3128(3) -0.05378(7) 1.000 0.0401(6) d . . .
O2 O Uani 0.35257(16) -0.0221(3) 0.04824(11) 1.000 0.0642(9) d . . .
H2 H Uiso 0.13540 0.41520 0.44130 1.000 0.0420 d . . .
H3 H Uiso 0.28590 0.44540 0.45000 1.000 0.0400 d . . .
H4 H Uiso 0.38400 0.36110 0.39140 1.000 0.0330 d . . .
H6 H Uiso 0.48260 0.14320 0.22120 1.000 0.0290 d . . .
H7 H Uiso 0.40210 0.02060 0.15130 1.000 0.0290 d . . .
H81A H Uiso 0.23100 -0.07290 0.13670 1.000 0.0270 d . . .
H81B H Uiso 0.16560 -0.06150 0.18350 1.000 0.0270 d . . .
H82A H Uiso 0.19440 0.18380 0.11260 1.000 0.0290 d . . .
H82B H Uiso 0.13490 0.20600 0.16140 1.000 0.0290 d . . .
H83A H Uiso 0.09160 -0.00120 0.08600 1.000 0.0300 d . . .
H83B H Uiso 0.03730 0.02240 0.12980 1.000 0.0300 d . . .
H83C H Uiso 0.04580 0.14540 0.09340 1.000 0.0300 d . . .
H1A H Uiso 0.03810 -0.27880 -0.02470 1.000 0.0480 d . . .
H1B H Uiso -0.03750 -0.37480 -0.04600 1.000 0.0480 d . . .
H2A H Uiso 0.29620 -0.05680 0.03960 1.000 0.0770 d . . .
H2B H Uiso 0.35100 0.08370 0.04910 1.000 0.0770 d . . .


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

# 10. MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O11 1.4302(18) . . yes
S1 O12 1.4407(18) . . yes
S1 C2 1.711(3) . . yes
S1 C9A 1.739(2) . . yes
O5 C5 1.217(3) . . yes
O9 C9 1.227(3) . . yes
O1 H1B 0.9000 . . no
O1 H1A 0.9000 . . no
O2 H2A 0.9000 . . no
O2 H2B 0.8800 . . no
N4 C3 1.358(3) . . yes
N4 C4A 1.336(3) . . yes
N6 C7 1.349(3) . . yes
N6 C5A 1.348(3) . . yes
N83 C82 1.481(3) . . yes
N4 H4 0.8600 . . no
N6 H6 0.8600 . . no
N83 H83C 0.8600 . . no
N83 H83B 0.8600 . . no
N83 H83A 0.8600 . . no
C2 C3 1.328(4) . . no
C4A C9A 1.375(3) . . no
C4A C5 1.518(3) . . no
C5 C5A 1.429(3) . . no
C5A C8A 1.392(3) . . no
C7 C8 1.382(3) . . no
C8 C81 1.496(3) . . no
C8 C8A 1.411(3) . . no
C8A C9 1.451(3) . . no
C9 C9A 1.476(3) . . no
C81 C82 1.513(3) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C7 H7 0.9500 . . no
C81 H81B 0.9500 . . no
C81 H81A 0.9500 . . no
C82 H82A 0.9500 . . no
C82 H82B 0.9500 . . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S1 O12 114.38(11) . . . yes
O11 S1 C2 110.24(13) . . . yes
O11 S1 C9A 111.97(11) . . . yes
O12 S1 C2 109.02(13) . . . yes
O12 S1 C9A 108.88(11) . . . yes
C2 S1 C9A 101.55(12) . . . yes
H1A O1 H1B 110.00 . . . no
H2A O2 H2B 108.00 . . . no
C3 N4 C4A 123.9(2) . . . yes
C5A N6 C7 109.27(18) . . . yes
C3 N4 H4 118.00 . . . no
C4A N4 H4 118.00 . . . no
C7 N6 H6 125.00 . . . no
C5A N6 H6 125.00 . . . no
H83A N83 H83B 109.00 . . . no
H83A N83 H83C 109.00 . . . no
C82 N83 H83A 110.00 . . . no
C82 N83 H83C 110.00 . . . no
H83B N83 H83C 109.00 . . . no
C82 N83 H83B 110.00 . . . no
S1 C2 C3 124.2(2) . . . yes
N4 C3 C2 124.2(2) . . . yes
C5 C4A C9A 122.4(2) . . . no
N4 C4A C5 113.21(19) . . . yes
N4 C4A C9A 124.4(2) . . . yes
O5 C5 C4A 119.5(2) . . . yes
C4A C5 C5A 113.78(18) . . . no
O5 C5 C5A 126.8(2) . . . yes
N6 C5A C8A 108.1(2) . . . yes
C5 C5A C8A 124.4(2) . . . no
N6 C5A C5 127.4(2) . . . yes
N6 C7 C8 109.6(2) . . . yes
C7 C8 C8A 105.7(2) . . . no
C7 C8 C81 127.4(2) . . . no
C8A C8 C81 127.0(2) . . . no
C5A C8A C9 121.7(2) . . . no
C8 C8A C9 131.0(2) . . . no
C5A C8A C8 107.34(19) . . . no
O9 C9 C8A 122.5(2) . . . yes
O9 C9 C9A 121.4(2) . . . yes
C8A C9 C9A 116.08(19) . . . no
C4A C9A C9 121.6(2) . . . no
S1 C9A C9 116.66(15) . . . yes
S1 C9A C4A 121.72(18) . . . yes
C8 C81 C82 111.5(2) . . . no
N83 C82 C81 110.52(19) . . . yes
S1 C2 H2 118.00 . . . no
C3 C2 H2 118.00 . . . no
N4 C3 H3 118.00 . . . no
C2 C3 H3 118.00 . . . no
C8 C7 H7 125.00 . . . no
N6 C7 H7 125.00 . . . no
C82 C81 H81A 109.00 . . . no
C8 C81 H81A 109.00 . . . no
C8 C81 H81B 109.00 . . . no
H81A C81 H81B 109.00 . . . no
C82 C81 H81B 109.00 . . . no
N83 C82 H82B 109.00 . . . no
N83 C82 H82A 109.00 . . . no
H82A C82 H82B 109.00 . . . no
C81 C82 H82A 109.00 . . . no
C81 C82 H82B 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S1 C2 C3 118.7(3) . . . . no
O12 S1 C2 C3 -115.0(3) . . . . no
C9A S1 C2 C3 -0.2(3) . . . . no
O11 S1 C9A C4A -118.8(2) . . . . no
O11 S1 C9A C9 62.6(2) . . . . no
O12 S1 C9A C4A 113.8(2) . . . . no
O12 S1 C9A C9 -64.9(2) . . . . no
C2 S1 C9A C4A -1.2(2) . . . . no
C2 S1 C9A C9 -179.8(2) . . . . no
C4A N4 C3 C2 1.5(4) . . . . no
C3 N4 C4A C5 176.5(2) . . . . no
C3 N4 C4A C9A -3.1(4) . . . . no
C7 N6 C5A C5 177.5(2) . . . . no
C7 N6 C5A C8A 0.4(3) . . . . no
C5A N6 C7 C8 -0.4(3) . . . . no
S1 C2 C3 N4 0.1(4) . . . . no
N4 C4A C5 O5 0.5(3) . . . . no
N4 C4A C5 C5A -179.2(2) . . . . no
C9A C4A C5 O5 -179.9(2) . . . . no
C9A C4A C5 C5A 0.4(3) . . . . no
N4 C4A C9A S1 2.9(4) . . . . no
N4 C4A C9A C9 -178.6(2) . . . . no
C5 C4A C9A S1 -176.70(18) . . . . no
C5 C4A C9A C9 1.8(4) . . . . no
O5 C5 C5A N6 1.2(4) . . . . no
O5 C5 C5A C8A 177.9(2) . . . . no
C4A C5 C5A N6 -179.2(2) . . . . no
C4A C5 C5A C8A -2.6(4) . . . . no
N6 C5A C8A C8 -0.2(3) . . . . no
N6 C5A C8A C9 179.6(2) . . . . no
C5 C5A C8A C8 -177.4(2) . . . . no
C5 C5A C8A C9 2.4(4) . . . . no
N6 C7 C8 C8A 0.2(3) . . . . no
N6 C7 C8 C81 179.1(2) . . . . no
C7 C8 C8A C5A 0.0(3) . . . . no
C7 C8 C8A C9 -179.8(3) . . . . no
C81 C8 C8A C5A -178.9(2) . . . . no
C81 C8 C8A C9 1.3(4) . . . . no
C7 C8 C81 C82 -101.8(3) . . . . no
C8A C8 C81 C82 76.8(3) . . . . no
C5A C8A C9 O9 -179.3(2) . . . . no
C5A C8A C9 C9A 0.1(3) . . . . no
C8 C8A C9 O9 0.4(4) . . . . no
C8 C8A C9 C9A 179.8(2) . . . . no
O9 C9 C9A S1 -4.1(3) . . . . no
O9 C9 C9A C4A 177.3(2) . . . . no
C8A C9 C9A S1 176.53(18) . . . . no
C8A C9 C9A C4A -2.1(4) . . . . no
C8 C81 C82 N83 -174.98(18) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1A Cl 0.9000 2.3400 3.181(2) 155.00 . yes
O1 H1B O2 0.9000 1.8200 2.692(3) 163.00 3_445 yes
O2 H2A Cl 0.9000 2.2700 3.166(3) 176.00 . yes
O2 H2B Cl 0.8800 2.2900 3.143(3) 161.00 7_555 yes
N4 H4 O5 0.8600 2.2700 2.648(3) 107.00 . yes
N4 H4 O1 0.8600 2.1300 2.872(3) 144.00 2_555 yes
N4 H4 O11 0.8600 2.5200 2.930(3) 110.00 7_555 yes
N6 H6 O9 0.8600 2.0500 2.884(2) 164.00 6_555 yes
N83 H83A Cl 0.8600 2.2600 3.112(2) 171.00 . yes
N83 H83B O12 0.8600 2.0100 2.853(3) 166.00 4_545 yes
N83 H83C O1 0.8600 1.9200 2.782(3) 175.00 5_555 yes
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9_1100rd25_RAD321
_database_code_depnum_ccdc_archive 'CCDC 998931'
_audit_update_record             
;
2014-04-23 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            'Thiaplakortone A Propylamide  DMSO'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N3 O5 S, C2 H6 O S'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H21 N3 O6 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         427.51
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   10.0722(6)
_cell_length_b                   24.9481(18)
_cell_length_c                   7.5588(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.053(6)
_cell_angle_gamma                90
_cell_volume                     1875.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    199.9(3)
_cell_measurement_reflns_used    1623
_cell_measurement_theta_min      3.6540
_cell_measurement_theta_max      29.1290

_exptl_crystal_description       plate
_exptl_crystal_colour            orange

_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.040
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.326
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent, 2012),
;
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  0.987

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      199.9(3)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measurement_method       'ω scans'

# number of measured reflections (redundant set)
_diffrn_reflns_number            7560
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             4251
# number of observed reflections (> n sig(I))
_reflns_number_gt                3062
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlis Pro(Oxford Diffraction, 2012)'
_computing_cell_refinement       'CrysAlis Pro'
_computing_data_reduction        'CrysAlis Pro'
_computing_structure_refinement  
'TeXSan (Molecular Structure Corporation, 2001), SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009), Westrip, 2010)'
#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+1.2305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none

_refine_ls_number_reflns         4251
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.070

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S Uani 0.07104(7) 0.07943(3) 0.46170(9) 1.000 0.0244(2) d . . .
O3 O Uani 0.41226(19) 0.21948(9) 0.7295(3) 1.000 0.0346(7) d . . .
O9 O Uani -0.07420(18) 0.17657(8) 0.3439(3) 1.000 0.0269(6) d . . .
O11 O Uani 0.0345(2) 0.06972(8) 0.2722(3) 1.000 0.0356(7) d . . .
O12 O Uani -0.0323(2) 0.06909(9) 0.5679(3) 1.000 0.0404(8) d . . .
O84 O Uani -0.3725(2) 0.41101(9) 0.2923(3) 1.000 0.0354(7) d . . .
N4 N Uani 0.3442(2) 0.11754(10) 0.6653(3) 1.000 0.0248(7) d . . .
N6 N Uani 0.2248(2) 0.30671(10) 0.5797(3) 1.000 0.0252(7) d . . .
N83 N Uani -0.1943(2) 0.37953(10) 0.4822(3) 1.000 0.0239(7) d . . .
C2 C Uani 0.2128(3) 0.04252(12) 0.5425(4) 1.000 0.0295(9) d . . .
C3 C Uani 0.3252(3) 0.06394(12) 0.6305(4) 1.000 0.0266(9) d . . .
C4A C Uani 0.2544(3) 0.15515(11) 0.5979(3) 1.000 0.0205(8) d . . .
C5 C Uani 0.3031(3) 0.21226(12) 0.6392(3) 1.000 0.0221(8) d . . .
C5A C Uani 0.2079(3) 0.25253(11) 0.5657(4) 1.000 0.0218(8) d . . .
C7 C Uani 0.1149(3) 0.33074(12) 0.4910(4) 1.000 0.0258(8) d . . .
C8 C Uani 0.0209(3) 0.29264(11) 0.4175(3) 1.000 0.0221(8) d . . .
C8A C Uani 0.0832(3) 0.24270(11) 0.4658(3) 1.000 0.0191(8) d . . .
C9 C Uani 0.0357(3) 0.18775(11) 0.4287(3) 1.000 0.0202(8) d . . .
C9A C Uani 0.1310(3) 0.14479(11) 0.5004(3) 1.000 0.0192(8) d . . .
C81 C Uani -0.1157(3) 0.30340(11) 0.3155(4) 1.000 0.0249(8) d . . .
C82 C Uani -0.2167(3) 0.32348(11) 0.4339(4) 1.000 0.0237(8) d . . .
C84 C Uani -0.2684(3) 0.41926(12) 0.4001(4) 1.000 0.0244(8) d . . .
C85 C Uani -0.2161(3) 0.47521(12) 0.4430(4) 1.000 0.0323(9) d . . .
C86 C Uani -0.3214(3) 0.51853(13) 0.4042(5) 1.000 0.0401(11) d . . .
S2 S Uani -0.43807(7) 0.14992(3) 0.26435(10) 1.000 0.0281(2) d . . .
O2 O Uani -0.5829(2) 0.13919(9) 0.2843(3) 1.000 0.0345(7) d . . .
C21 C Uani -0.3743(3) 0.19210(13) 0.4453(4) 1.000 0.0366(10) d . . .
C22 C Uani -0.3511(3) 0.09055(14) 0.3417(4) 1.000 0.0373(10) d . . .
H2 H Uiso 0.20970 0.00490 0.52320 1.000 0.0350 d . . .
H3 H Uiso 0.39730 0.04010 0.67150 1.000 0.0310 d . . .
H4 H Uiso 0.41720 0.12770 0.73320 1.000 0.0290 d . . .
H6 H Uiso 0.29540 0.32310 0.63700 1.000 0.0290 d . . .
H7 H Uiso 0.10170 0.36850 0.47970 1.000 0.0300 d . . .
H81A H Uiso -0.10840 0.33000 0.22780 1.000 0.0280 d . . .
H81B H Uiso -0.15030 0.27130 0.25900 1.000 0.0280 d . . .
H82A H Uiso -0.30500 0.31980 0.37000 1.000 0.0280 d . . .
H82B H Uiso -0.20720 0.30260 0.54000 1.000 0.0280 d . . .
H83 H Uiso -0.13010 0.38750 0.56890 1.000 0.0280 d . . .
H85A H Uiso -0.18070 0.47680 0.56740 1.000 0.0380 d . . .
H85B H Uiso -0.14680 0.48240 0.37500 1.000 0.0380 d . . .
H86A H Uiso -0.28410 0.55270 0.43790 1.000 0.0490 d . . .
H86B H Uiso -0.39450 0.51180 0.46770 1.000 0.0490 d . . .
H86C H Uiso -0.35610 0.51910 0.27830 1.000 0.0490 d . . .
H21A H Uiso -0.42190 0.22530 0.43790 1.000 0.0430 d . . .
H21B H Uiso -0.28110 0.19950 0.44510 1.000 0.0430 d . . .
H21C H Uiso -0.38300 0.17530 0.55700 1.000 0.0430 d . . .
H22A H Uiso -0.25630 0.09600 0.35080 1.000 0.0450 d . . .
H22B H Uiso -0.37190 0.08050 0.45440 1.000 0.0450 d . . .
H22C H Uiso -0.37630 0.06200 0.25750 1.000 0.0450 d . . .


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

# 10. MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O11 1.442(2) . . yes
S1 O12 1.434(2) . . yes
S1 C2 1.728(3) . . yes
S1 C9A 1.748(3) . . yes
S2 C21 1.765(3) . . yes
S2 C22 1.773(3) . . yes
S2 O2 1.514(2) . . yes
O3 C5 1.213(3) . . yes
O9 C9 1.221(3) . . yes
O84 C84 1.240(4) . . yes
N4 C3 1.370(4) . . yes
N4 C4A 1.347(4) . . yes
N6 C5A 1.364(4) . . yes
N6 C7 1.342(4) . . yes
N83 C82 1.454(4) . . yes
N83 C84 1.334(4) . . yes
N4 H4 0.8700 . . no
N6 H6 0.8700 . . no
N83 H83 0.8700 . . no
C2 C3 1.331(4) . . no
C4A C9A 1.366(4) . . no
C4A C5 1.523(4) . . no
C5 C5A 1.439(4) . . no
C5A C8A 1.382(4) . . no
C7 C8 1.394(4) . . no
C8 C8A 1.417(4) . . no
C8 C81 1.492(4) . . no
C8A C9 1.465(4) . . no
C9 C9A 1.483(4) . . no
C81 C82 1.541(4) . . no
C84 C85 1.509(4) . . no
C85 C86 1.510(4) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C7 H7 0.9500 . . no
C81 H81A 0.9500 . . no
C81 H81B 0.9500 . . no
C82 H82A 0.9500 . . no
C82 H82B 0.9500 . . no
C85 H85B 0.9500 . . no
C85 H85A 0.9500 . . no
C86 H86A 0.9500 . . no
C86 H86B 0.9500 . . no
C86 H86C 0.9600 . . no
C21 H21A 0.9500 . . no
C21 H21B 0.9600 . . no
C21 H21C 0.9600 . . no
C22 H22A 0.9600 . . no
C22 H22B 0.9400 . . no
C22 H22C 0.9600 . . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 S1 O12 115.56(13) . . . yes
O11 S1 C2 109.22(13) . . . yes
O11 S1 C9A 110.52(12) . . . yes
O12 S1 C2 109.78(14) . . . yes
O12 S1 C9A 109.65(13) . . . yes
C2 S1 C9A 101.16(14) . . . yes
O2 S2 C21 105.50(14) . . . yes
O2 S2 C22 104.68(14) . . . yes
C21 S2 C22 98.16(15) . . . yes
C3 N4 C4A 122.8(2) . . . yes
C5A N6 C7 108.7(2) . . . yes
C82 N83 C84 123.0(2) . . . yes
C4A N4 H4 119.00 . . . no
C3 N4 H4 119.00 . . . no
C5A N6 H6 126.00 . . . no
C7 N6 H6 126.00 . . . no
C84 N83 H83 118.00 . . . no
C82 N83 H83 119.00 . . . no
S1 C2 C3 123.6(2) . . . yes
N4 C3 C2 124.7(3) . . . yes
N4 C4A C9A 124.9(3) . . . yes
N4 C4A C5 113.5(2) . . . yes
C5 C4A C9A 121.6(2) . . . no
O3 C5 C4A 119.2(3) . . . yes
C4A C5 C5A 113.6(2) . . . no
O3 C5 C5A 127.1(3) . . . yes
N6 C5A C5 126.5(3) . . . yes
N6 C5A C8A 108.1(2) . . . yes
C5 C5A C8A 125.5(3) . . . no
N6 C7 C8 110.5(3) . . . yes
C8A C8 C81 128.8(3) . . . no
C7 C8 C8A 104.6(2) . . . no
C7 C8 C81 126.6(3) . . . no
C8 C8A C9 131.0(3) . . . no
C5A C8A C8 108.2(2) . . . no
C5A C8A C9 120.8(3) . . . no
C8A C9 C9A 115.7(2) . . . no
O9 C9 C9A 120.5(2) . . . yes
O9 C9 C8A 123.8(3) . . . yes
S1 C9A C9 115.2(2) . . . yes
C4A C9A C9 122.8(3) . . . no
S1 C9A C4A 121.9(2) . . . yes
C8 C81 C82 113.5(2) . . . no
N83 C82 C81 111.6(2) . . . yes
O84 C84 N83 122.4(3) . . . yes
N83 C84 C85 115.9(3) . . . yes
O84 C84 C85 121.7(3) . . . yes
C84 C85 C86 114.2(3) . . . no
C3 C2 H2 119.00 . . . no
S1 C2 H2 118.00 . . . no
N4 C3 H3 118.00 . . . no
C2 C3 H3 117.00 . . . no
N6 C7 H7 125.00 . . . no
C8 C7 H7 124.00 . . . no
C82 C81 H81A 108.00 . . . no
H81A C81 H81B 110.00 . . . no
C8 C81 H81B 109.00 . . . no
C82 C81 H81B 108.00 . . . no
C8 C81 H81A 109.00 . . . no
N83 C82 H82A 109.00 . . . no
H82A C82 H82B 110.00 . . . no
C81 C82 H82B 109.00 . . . no
N83 C82 H82B 109.00 . . . no
C81 C82 H82A 109.00 . . . no
C84 C85 H85A 108.00 . . . no
C84 C85 H85B 109.00 . . . no
C86 C85 H85A 108.00 . . . no
C86 C85 H85B 108.00 . . . no
H85A C85 H85B 110.00 . . . no
C85 C86 H86C 110.00 . . . no
H86A C86 H86C 109.00 . . . no
H86B C86 H86C 108.00 . . . no
H86A C86 H86B 109.00 . . . no
C85 C86 H86A 111.00 . . . no
C85 C86 H86B 110.00 . . . no
S2 C21 H21A 111.00 . . . no
S2 C21 H21B 111.00 . . . no
S2 C21 H21C 110.00 . . . no
H21A C21 H21B 108.00 . . . no
H21A C21 H21C 108.00 . . . no
H21B C21 H21C 108.00 . . . no
S2 C22 H22A 110.00 . . . no
S2 C22 H22B 111.00 . . . no
S2 C22 H22C 110.00 . . . no
H22A C22 H22B 110.00 . . . no
H22A C22 H22C 108.00 . . . no
H22B C22 H22C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S1 C2 C3 124.5(3) . . . . no
O12 S1 C2 C3 -107.9(3) . . . . no
C9A S1 C2 C3 8.0(3) . . . . no
O11 S1 C9A C4A -124.5(2) . . . . no
O11 S1 C9A C9 58.7(2) . . . . no
O12 S1 C9A C4A 107.0(2) . . . . no
O12 S1 C9A C9 -69.8(2) . . . . no
C2 S1 C9A C4A -8.9(3) . . . . no
C2 S1 C9A C9 174.3(2) . . . . no
C4A N4 C3 C2 -6.7(4) . . . . no
C3 N4 C4A C5 -174.2(2) . . . . no
C3 N4 C4A C9A 5.4(4) . . . . no
C7 N6 C5A C5 178.9(3) . . . . no
C7 N6 C5A C8A -0.3(3) . . . . no
C5A N6 C7 C8 0.8(3) . . . . no
C84 N83 C82 C81 100.6(3) . . . . no
C82 N83 C84 O84 9.5(4) . . . . no
C82 N83 C84 C85 -169.1(2) . . . . no
S1 C2 C3 N4 -1.3(5) . . . . no
N4 C4A C5 O3 -1.9(3) . . . . no
N4 C4A C5 C5A 179.4(2) . . . . no
C9A C4A C5 O3 178.4(2) . . . . no
C9A C4A C5 C5A -0.3(4) . . . . no
N4 C4A C9A S1 3.6(4) . . . . no
N4 C4A C9A C9 -179.9(2) . . . . no
C5 C4A C9A S1 -176.82(19) . . . . no
C5 C4A C9A C9 -0.3(4) . . . . no
O3 C5 C5A N6 2.1(5) . . . . no
O3 C5 C5A C8A -178.8(3) . . . . no
C4A C5 C5A N6 -179.3(3) . . . . no
C4A C5 C5A C8A -0.2(4) . . . . no
N6 C5A C8A C8 -0.3(3) . . . . no
N6 C5A C8A C9 -179.6(2) . . . . no
C5 C5A C8A C8 -179.5(3) . . . . no
C5 C5A C8A C9 1.2(4) . . . . no
N6 C7 C8 C8A -1.0(3) . . . . no
N6 C7 C8 C81 177.5(3) . . . . no
C7 C8 C8A C5A 0.8(3) . . . . no
C7 C8 C8A C9 179.9(3) . . . . no
C81 C8 C8A C5A -177.7(3) . . . . no
C81 C8 C8A C9 1.4(5) . . . . no
C7 C8 C81 C82 -72.5(4) . . . . no
C8A C8 C81 C82 105.7(3) . . . . no
C5A C8A C9 O9 178.8(3) . . . . no
C5A C8A C9 C9A -1.7(4) . . . . no
C8 C8A C9 O9 -0.3(4) . . . . no
C8 C8A C9 C9A 179.3(3) . . . . no
O9 C9 C9A S1 -2.4(3) . . . . no
O9 C9 C9A C4A -179.2(3) . . . . no
C8A C9 C9A S1 177.96(18) . . . . no
C8A C9 C9A C4A 1.2(4) . . . . no
C8 C81 C82 N83 76.6(3) . . . . no
O84 C84 C85 C86 22.1(4) . . . . no
N83 C84 C85 C86 -159.3(3) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N4 H4 O3 0.8700 2.2900 2.659(3) 106.00 . yes
N4 H4 O84 0.8700 2.3100 2.951(3) 131.00 4_655 yes
N6 H6 S2 0.8700 2.7900 3.627(2) 162.00 4_655 yes
N6 H6 O2 0.8700 1.7900 2.650(3) 168.00 4_655 yes
N83 H83 O11 0.8700 2.3300 3.183(3) 166.00 4_555 yes
C2 H2 O12 0.9500 2.5900 3.358(4) 139.00 3_556 yes
C21 H21A O3 0.9500 2.5200 3.323(4) 142.00 4_454 yes
C21 H21B O9 0.9600 2.4000 3.256(4) 149.00 . yes
C22 H22B O84 0.9400 2.5600 3.447(4) 156.00 4_555 yes
C81 H81B O9 0.9500 2.5400 3.195(3) 127.00 . yes
C82 H82A O84 0.9500 2.4200 2.802(4) 104.00 . yes
C82 H82B O9 0.9500 2.5200 3.204(4) 129.00 4_555 yes

#===END
