# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_FO6808
_database_code_depnum_ccdc_archive 'CCDC 1904792'
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O7 S'
_chemical_formula_sum            'C15 H17 N O7 S'
_chemical_formula_weight         355.36

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'


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                   7.2163(2)
_cell_length_b                   12.4415(2)
_cell_length_c                   17.8306(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.925(1)
_cell_angle_gamma                90
_cell_volume                     1589.18(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    9494
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.082
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6978
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9494
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3633
_reflns_number_gt                3350
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0248P)²+3.1470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3633
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.204
_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 0.50009(8) 0.22966(5) 0.35148(3) 0.01678(15) Uani 1 1 d . . .
O1 O 0.6853(2) 0.37090(13) 0.53276(9) 0.0162(3) Uani 1 1 d . . .
O2 O 0.6381(3) 0.68751(13) 0.41305(10) 0.0188(4) Uani 1 1 d . . .
H1O2 H 0.533(5) 0.678(3) 0.433(2) 0.040(10) Uiso 1 1 d . . .
O3 O 1.0310(2) 0.42710(14) 0.37956(10) 0.0200(4) Uani 1 1 d . . .
O4 O 0.9336(3) 0.48366(15) 0.26197(10) 0.0230(4) Uani 1 1 d . . .
O5 O 0.4308(2) 0.33614(13) 0.39210(9) 0.0159(3) Uani 1 1 d . . .
O6 O 0.5820(3) 0.26317(15) 0.28624(10) 0.0233(4) Uani 1 1 d . . .
O7 O 0.3382(3) 0.16324(15) 0.34473(11) 0.0259(4) Uani 1 1 d . . .
N1 N 0.7579(3) 0.52901(16) 0.47566(11) 0.0147(4) Uani 1 1 d . . .
H1N1 H 0.836(4) 0.553(2) 0.5141(16) 0.017(7) Uiso 1 1 d . . .
C1 C 0.6726(3) 0.43361(18) 0.47905(13) 0.0136(4) Uani 1 1 d . . .
C2 C 0.5542(3) 0.42204(18) 0.40464(13) 0.0142(4) Uani 1 1 d . . .
C3 C 0.5677(3) 0.50778(19) 0.36156(13) 0.0150(4) Uani 1 1 d . . .
C4 C 0.7109(3) 0.58428(18) 0.40356(13) 0.0155(5) Uani 1 1 d . . .
C5 C 0.8834(3) 0.6006(2) 0.36169(14) 0.0180(5) Uani 1 1 d . . .
H5B H 0.984(4) 0.636(2) 0.3971(17) 0.023(8) Uiso 1 1 d . . .
H5A H 0.848(4) 0.645(2) 0.3184(17) 0.023(8) Uiso 1 1 d . . .
C6 C 0.9586(3) 0.4951(2) 0.33727(13) 0.0162(5) Uani 1 1 d . . .
C7 C 0.9944(4) 0.3820(3) 0.23370(16) 0.0279(6) Uani 1 1 d . . .
H7C H 0.894(5) 0.328(3) 0.239(2) 0.043(10) Uiso 1 1 d . . .
H7B H 1.007(4) 0.392(2) 0.1812(18) 0.025(8) Uiso 1 1 d . . .
H7A H 1.113(6) 0.360(3) 0.260(2) 0.051(11) Uiso 1 1 d . . .
C8 C 0.4654(4) 0.5373(2) 0.28734(15) 0.0223(5) Uani 1 1 d . . .
H8C H 0.385(4) 0.481(2) 0.2657(17) 0.022(7) Uiso 1 1 d . . .
H8B H 0.556(5) 0.556(3) 0.2504(19) 0.034(9) Uiso 1 1 d . . .
H8A H 0.388(5) 0.597(3) 0.2928(19) 0.036(9) Uiso 1 1 d . . .
C9 C 0.6720(3) 0.17935(18) 0.41961(13) 0.0167(5) Uani 1 1 d . . .
C10 C 0.6188(4) 0.1230(2) 0.48090(15) 0.0204(5) Uani 1 1 d . . .
H10 H 0.488(4) 0.108(2) 0.4823(16) 0.022(7) Uiso 1 1 d . . .
C11 C 0.7537(4) 0.0937(2) 0.53909(15) 0.0222(5) Uani 1 1 d . . .
H11 H 0.720(5) 0.058(3) 0.581(2) 0.038(9) Uiso 1 1 d . . .
C12 C 0.9413(4) 0.12156(19) 0.53749(14) 0.0204(5) Uani 1 1 d . . .
C13 C 0.9909(3) 0.1759(2) 0.47494(14) 0.0196(5) Uani 1 1 d . . .
H13 H 1.120(4) 0.196(2) 0.4703(16) 0.021(7) Uiso 1 1 d . . .
C14 C 0.8584(3) 0.20432(19) 0.41504(14) 0.0173(5) Uani 1 1 d . . .
H14 H 0.893(4) 0.240(2) 0.3686(15) 0.010(6) Uiso 1 1 d . . .
C15 C 1.0848(4) 0.0944(2) 0.60295(17) 0.0283(6) Uani 1 1 d . . .
H15C H 1.067(6) 0.130(3) 0.650(2) 0.063(13) Uiso 1 1 d . . .
H15B H 1.087(6) 0.021(4) 0.613(2) 0.067(13) Uiso 1 1 d . . .
H15A H 1.210(7) 0.119(4) 0.594(2) 0.068(13) Uiso 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 O7 1.4242(18) . ?
S1 O6 1.4289(19) . ?
S1 O5 1.6177(17) . ?
S1 C9 1.744(2) . ?
O1 C1 1.230(3) . ?
O2 C4 1.405(3) . ?
O2 H1O2 0.89(4) . ?
O3 C6 1.209(3) . ?
O4 C6 1.341(3) . ?
O4 C7 1.449(3) . ?
O5 C2 1.392(3) . ?
N1 C1 1.342(3) . ?
N1 C4 1.461(3) . ?
N1 H1N1 0.89(3) . ?
C1 C2 1.496(3) . ?
C2 C3 1.325(3) . ?
C3 C8 1.482(3) . ?
C3 C4 1.532(3) . ?
C4 C5 1.540(3) . ?
C5 C6 1.505(3) . ?
C5 H5B 1.01(3) . ?
C5 H5A 0.96(3) . ?
C7 H7C 1.00(4) . ?
C7 H7B 0.96(3) . ?
C7 H7A 0.96(4) . ?
C8 H8C 0.96(3) . ?
C8 H8B 1.01(3) . ?
C8 H8A 0.95(4) . ?
C9 C10 1.391(3) . ?
C9 C14 1.393(3) . ?
C10 C11 1.383(4) . ?
C10 H10 0.97(3) . ?
C11 C12 1.401(4) . ?
C11 H11 0.93(4) . ?
C12 C13 1.387(4) . ?
C12 C15 1.502(4) . ?
C13 C14 1.391(3) . ?
C13 H13 0.98(3) . ?
C14 H14 1.00(3) . ?
C15 H15C 0.98(4) . ?
C15 H15B 0.93(5) . ?
C15 H15A 0.98(5) . ?

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
O7 S1 O6 121.06(12) . . ?
O7 S1 O5 102.61(10) . . ?
O6 S1 O5 107.82(10) . . ?
O7 S1 C9 110.97(12) . . ?
O6 S1 C9 110.04(11) . . ?
O5 S1 C9 102.37(10) . . ?
C4 O2 H1O2 106(2) . . ?
C6 O4 C7 115.5(2) . . ?
C2 O5 S1 118.33(14) . . ?
C1 N1 C4 113.38(19) . . ?
C1 N1 H1N1 121.2(19) . . ?
C4 N1 H1N1 125.4(19) . . ?
O1 C1 N1 127.2(2) . . ?
O1 C1 C2 127.6(2) . . ?
N1 C1 C2 105.15(19) . . ?
C3 C2 O5 128.0(2) . . ?
C3 C2 C1 111.3(2) . . ?
O5 C2 C1 120.16(19) . . ?
C2 C3 C8 130.8(2) . . ?
C2 C3 C4 108.0(2) . . ?
C8 C3 C4 121.1(2) . . ?
O2 C4 N1 112.00(19) . . ?
O2 C4 C3 112.76(19) . . ?
N1 C4 C3 102.07(18) . . ?
O2 C4 C5 105.89(18) . . ?
N1 C4 C5 111.88(19) . . ?
C3 C4 C5 112.43(19) . . ?
C6 C5 C4 111.51(19) . . ?
C6 C5 H5B 107.9(17) . . ?
C4 C5 H5B 108.6(17) . . ?
C6 C5 H5A 110.1(18) . . ?
C4 C5 H5A 108.3(18) . . ?
H5B C5 H5A 111(2) . . ?
O3 C6 O4 123.1(2) . . ?
O3 C6 C5 125.0(2) . . ?
O4 C6 C5 111.9(2) . . ?
O4 C7 H7C 108(2) . . ?
O4 C7 H7B 106.9(19) . . ?
H7C C7 H7B 110(3) . . ?
O4 C7 H7A 111(2) . . ?
H7C C7 H7A 112(3) . . ?
H7B C7 H7A 109(3) . . ?
C3 C8 H8C 112.8(18) . . ?
C3 C8 H8B 110.3(19) . . ?
H8C C8 H8B 108(3) . . ?
C3 C8 H8A 110(2) . . ?
H8C C8 H8A 106(3) . . ?
H8B C8 H8A 109(3) . . ?
C10 C9 C14 121.2(2) . . ?
C10 C9 S1 119.18(19) . . ?
C14 C9 S1 119.34(19) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 122.0(18) . . ?
C9 C10 H10 118.9(18) . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 120(2) . . ?
C12 C11 H11 119(2) . . ?
C13 C12 C11 118.7(2) . . ?
C13 C12 C15 120.9(2) . . ?
C11 C12 C15 120.4(2) . . ?
C12 C13 C14 121.4(2) . . ?
C12 C13 H13 122.1(17) . . ?
C14 C13 H13 116.5(17) . . ?
C13 C14 C9 118.5(2) . . ?
C13 C14 H14 122.2(15) . . ?
C9 C14 H14 119.2(15) . . ?
C12 C15 H15C 115(3) . . ?
C12 C15 H15B 111(3) . . ?
H15C C15 H15B 107(4) . . ?
C12 C15 H15A 112(3) . . ?
H15C C15 H15A 102(3) . . ?
H15B C15 H15A 109(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_FO6412
_database_code_depnum_ccdc_archive 'CCDC 1904795'
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N2 O4'
_chemical_formula_sum            'C10 H12 N2 O4'
_chemical_formula_weight         224.22

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   7.8544(3)
_cell_length_b                   14.0260(6)
_cell_length_c                   9.9668(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.854(2)
_cell_angle_gamma                90
_cell_volume                     1026.07(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    13375
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.47

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.102
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6291
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13375
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2339
_reflns_number_gt                2074
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0276P)²+0.6449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2339
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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
O1 O 1.04002(13) 0.40626(8) 0.60783(12) 0.0268(3) Uani 1 1 d . . .
O2 O 0.60700(15) 0.12448(8) 0.47642(12) 0.0267(3) Uani 1 1 d . . .
H1O2 H 0.693(3) 0.080(2) 0.528(3) 0.068(8) Uiso 1 1 d . . .
O3 O 0.49326(15) 0.09171(8) 0.64732(12) 0.0274(3) Uani 1 1 d . . .
O4 O 0.64793(13) 0.49926(8) 0.87320(11) 0.0240(2) Uani 1 1 d . . .
N1 N 0.78112(15) 0.43179(9) 0.66393(13) 0.0185(3) Uani 1 1 d . . .
H1N1 H 0.826(3) 0.4704(15) 0.735(2) 0.036(5) Uiso 1 1 d . . .
N2 N 0.34126(18) 0.49993(10) 0.81408(14) 0.0226(3) Uani 1 1 d . . .
H1N2 H 0.349(3) 0.5260(14) 0.894(2) 0.032(5) Uiso 1 1 d . . .
N2N2 H 0.236(3) 0.4780(14) 0.756(2) 0.032(5) Uiso 1 1 d . . .
C1 C 0.87769(19) 0.39421(10) 0.58495(15) 0.0191(3) Uani 1 1 d . . .
C2 C 0.74772(19) 0.33535(10) 0.46940(14) 0.0187(3) Uani 1 1 d . . .
C3 C 0.58301(18) 0.34152(9) 0.48201(14) 0.0166(3) Uani 1 1 d . . .
C4 C 0.60001(18) 0.40312(9) 0.60691(14) 0.0164(3) Uani 1 1 d . . .
C5 C 0.8118(2) 0.28132(12) 0.36731(17) 0.0253(3) Uani 1 1 d . . .
H5C H 0.876(3) 0.3233(15) 0.323(2) 0.036(5) Uiso 1 1 d . . .
H5B H 0.710(3) 0.2504(15) 0.292(2) 0.043(6) Uiso 1 1 d . . .
H5A H 0.897(3) 0.2294(16) 0.418(2) 0.045(6) Uiso 1 1 d . . .
C6 C 0.40896(19) 0.29267(10) 0.39391(15) 0.0192(3) Uani 1 1 d . . .
H6B H 0.309(2) 0.3387(12) 0.3608(18) 0.021(4) Uiso 1 1 d . . .
H6A H 0.426(2) 0.2658(13) 0.3076(19) 0.024(4) Uiso 1 1 d . . .
C7 C 0.34976(19) 0.21386(10) 0.47591(16) 0.0212(3) Uani 1 1 d . . .
H7B H 0.310(2) 0.2393(13) 0.553(2) 0.027(4) Uiso 1 1 d . . .
H7A H 0.243(2) 0.1796(13) 0.4090(19) 0.029(5) Uiso 1 1 d . . .
C8 C 0.49003(19) 0.13774(10) 0.54334(15) 0.0198(3) Uani 1 1 d . . .
C9 C 0.46521(18) 0.42507(10) 0.65553(15) 0.0172(3) Uani 1 1 d . . .
H9 H 0.345(2) 0.4031(13) 0.6012(19) 0.025(4) Uiso 1 1 d . . .
C10 C 0.49149(18) 0.47864(10) 0.78803(15) 0.0180(3) 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
O1 C1 1.2244(17) . ?
O2 C8 1.3266(18) . ?
O2 H1O2 0.93(3) . ?
O3 C8 1.2136(17) . ?
O4 C10 1.2536(17) . ?
N1 C1 1.3776(18) . ?
N1 C4 1.3902(17) . ?
N1 H1N1 0.86(2) . ?
N2 C10 1.3293(18) . ?
N2 H1N2 0.86(2) . ?
N2 N2N2 0.88(2) . ?
C1 C2 1.4876(19) . ?
C2 C3 1.346(2) . ?
C2 C5 1.492(2) . ?
C3 C4 1.4818(19) . ?
C3 C6 1.5016(19) . ?
C4 C9 1.3475(19) . ?
C5 H5C 0.98(2) . ?
C5 H5B 0.99(2) . ?
C5 H5A 1.00(2) . ?
C6 C7 1.542(2) . ?
C6 H6B 0.976(17) . ?
C6 H6A 0.992(18) . ?
C7 C8 1.509(2) . ?
C7 H7B 0.992(19) . ?
C7 H7A 0.991(19) . ?
C9 C10 1.4686(19) . ?
C9 H9 0.956(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H1O2 108.6(16) . . ?
C1 N1 C4 110.31(12) . . ?
C1 N1 H1N1 123.9(13) . . ?
C4 N1 H1N1 125.6(13) . . ?
C10 N2 H1N2 120.3(13) . . ?
C10 N2 N2N2 119.1(13) . . ?
H1N2 N2 N2N2 119.7(18) . . ?
O1 C1 N1 126.12(13) . . ?
O1 C1 C2 127.07(13) . . ?
N1 C1 C2 106.80(12) . . ?
C3 C2 C1 108.02(12) . . ?
C3 C2 C5 131.65(13) . . ?
C1 C2 C5 120.32(13) . . ?
C2 C3 C4 108.29(12) . . ?
C2 C3 C6 128.40(13) . . ?
C4 C3 C6 123.25(12) . . ?
C9 C4 N1 127.41(13) . . ?
C9 C4 C3 126.02(12) . . ?
N1 C4 C3 106.57(11) . . ?
C2 C5 H5C 110.8(12) . . ?
C2 C5 H5B 111.4(12) . . ?
H5C C5 H5B 109.3(16) . . ?
C2 C5 H5A 110.8(12) . . ?
H5C C5 H5A 107.8(16) . . ?
H5B C5 H5A 106.5(17) . . ?
C3 C6 C7 113.63(11) . . ?
C3 C6 H6B 110.5(10) . . ?
C7 C6 H6B 107.2(10) . . ?
C3 C6 H6A 107.6(10) . . ?
C7 C6 H6A 110.4(10) . . ?
H6B C6 H6A 107.4(14) . . ?
C8 C7 C6 115.66(12) . . ?
C8 C7 H7B 107.0(10) . . ?
C6 C7 H7B 112.9(10) . . ?
C8 C7 H7A 105.5(11) . . ?
C6 C7 H7A 109.5(10) . . ?
H7B C7 H7A 105.6(14) . . ?
O3 C8 O2 123.17(13) . . ?
O3 C8 C7 123.13(13) . . ?
O2 C8 C7 113.69(12) . . ?
C4 C9 C10 124.29(13) . . ?
C4 C9 H9 117.7(11) . . ?
C10 C9 H9 118.0(11) . . ?
O4 C10 N2 122.69(13) . . ?
O4 C10 C9 121.13(12) . . ?
N2 C10 C9 116.11(12) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.191
_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_FO6701
_database_code_depnum_ccdc_archive 'CCDC 1904794'
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N2 O4'
_chemical_formula_sum            'C10 H12 N2 O4'
_chemical_formula_weight         224.22

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.6784(5)
_cell_length_b                   7.8448(5)
_cell_length_c                   9.1114(6)
_cell_angle_alpha                91.933(4)
_cell_angle_beta                 101.720(2)
_cell_angle_gamma                105.491(4)
_cell_volume                     515.61(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6485
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.042
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6270
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6485
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2328
_reflns_number_gt                1882
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       DENZO
_computing_cell_refinement       DENZO
_computing_data_reduction        COLLECT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0494P)²+0.5302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2328
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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
O1 O 0.7535(2) -0.1040(2) 0.46354(18) 0.0228(4) Uani 1 1 d . . .
O2 O 0.7953(2) 0.1705(2) 1.03155(18) 0.0243(4) Uani 1 1 d . . .
H1O2 H 0.732(5) 0.234(4) 1.068(4) 0.047(9) Uiso 1 1 d . . .
O3 O 0.5332(2) 0.0659(2) 0.85624(17) 0.0201(4) Uani 1 1 d . . .
O4 O 0.5879(2) 0.3475(2) 0.14086(17) 0.0204(4) Uani 1 1 d . . .
N1 N 0.7061(3) 0.1626(2) 0.3899(2) 0.0183(4) Uani 1 1 d . . .
H1N1 H 0.638(4) 0.116(4) 0.300(3) 0.030(7) Uiso 1 1 d . . .
N2 N 0.5986(3) 0.6329(3) 0.1965(2) 0.0214(4) Uani 1 1 d . . .
H2N2 H 0.628(4) 0.734(4) 0.267(3) 0.030(7) Uiso 1 1 d . . .
H1N2 H 0.556(4) 0.644(4) 0.096(4) 0.031(8) Uiso 1 1 d . . .
C1 C 0.7685(3) 0.0540(3) 0.4905(2) 0.0176(5) Uani 1 1 d . . .
C2 C 0.8546(3) 0.1649(3) 0.6355(2) 0.0177(5) Uani 1 1 d . . .
C3 C 0.8318(3) 0.3276(3) 0.6191(2) 0.0173(4) Uani 1 1 d . . .
C4 C 0.7390(3) 0.3313(3) 0.4603(2) 0.0172(4) Uani 1 1 d . . .
C5 C 0.9432(3) 0.0870(3) 0.7679(2) 0.0191(5) Uani 1 1 d . . .
H5B H 1.026(3) 0.187(3) 0.839(3) 0.016(6) Uiso 1 1 d . . .
H5A H 1.018(4) 0.013(4) 0.734(3) 0.035(8) Uiso 1 1 d . . .
C6 C 0.7972(3) -0.0373(3) 0.8391(3) 0.0186(5) Uani 1 1 d . . .
H6B H 0.717(4) -0.124(3) 0.764(3) 0.016(6) Uiso 1 1 d . . .
H6A H 0.852(4) -0.102(4) 0.919(3) 0.030(7) Uiso 1 1 d . . .
C7 C 0.6923(3) 0.0677(3) 0.9088(2) 0.0177(4) Uani 1 1 d . . .
C8 C 0.8859(3) 0.4849(3) 0.7327(3) 0.0220(5) Uani 1 1 d . . .
H8C H 0.955(4) 0.593(4) 0.700(3) 0.030(7) Uiso 1 1 d . . .
H8B H 0.955(4) 0.460(4) 0.829(3) 0.034(8) Uiso 1 1 d . . .
H8A H 0.777(5) 0.511(4) 0.757(3) 0.039(8) Uiso 1 1 d . . .
C9 C 0.7018(3) 0.4741(3) 0.3971(2) 0.0182(5) Uani 1 1 d . . .
H9 H 0.737(4) 0.588(3) 0.461(3) 0.019(6) Uiso 1 1 d . . .
C10 C 0.6255(3) 0.4785(3) 0.2353(2) 0.0170(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
O1 C1 1.225(3) . ?
O2 C7 1.329(3) . ?
O2 H1O2 0.88(4) . ?
O3 C7 1.214(3) . ?
O4 C10 1.249(3) . ?
N1 C1 1.375(3) . ?
N1 C4 1.387(3) . ?
N1 H1N1 0.89(3) . ?
N2 C10 1.330(3) . ?
N2 H2N2 0.95(3) . ?
N2 H1N2 0.92(3) . ?
C1 C2 1.483(3) . ?
C2 C3 1.343(3) . ?
C2 C5 1.493(3) . ?
C3 C4 1.482(3) . ?
C3 C8 1.494(3) . ?
C4 C9 1.348(3) . ?
C5 C6 1.544(3) . ?
C5 H5B 0.98(3) . ?
C5 H5A 1.00(3) . ?
C6 C7 1.503(3) . ?
C6 H6B 0.94(3) . ?
C6 H6A 0.99(3) . ?
C8 H8C 0.97(3) . ?
C8 H8B 0.98(3) . ?
C8 H8A 0.98(3) . ?
C9 C10 1.477(3) . ?
C9 H9 0.99(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H1O2 111(2) . . ?
C1 N1 C4 110.30(18) . . ?
C1 N1 H1N1 119.7(18) . . ?
C4 N1 H1N1 129.1(18) . . ?
C10 N2 H2N2 122.8(17) . . ?
C10 N2 H1N2 118.6(18) . . ?
H2N2 N2 H1N2 118(2) . . ?
O1 C1 N1 125.8(2) . . ?
O1 C1 C2 127.6(2) . . ?
N1 C1 C2 106.68(18) . . ?
C3 C2 C1 108.37(19) . . ?
C3 C2 C5 131.6(2) . . ?
C1 C2 C5 120.0(2) . . ?
C2 C3 C4 107.87(19) . . ?
C2 C3 C8 129.4(2) . . ?
C4 C3 C8 122.7(2) . . ?
C9 C4 N1 127.4(2) . . ?
C9 C4 C3 125.9(2) . . ?
N1 C4 C3 106.67(18) . . ?
C2 C5 C6 111.58(18) . . ?
C2 C5 H5B 107.3(14) . . ?
C6 C5 H5B 112.7(14) . . ?
C2 C5 H5A 109.1(18) . . ?
C6 C5 H5A 106.9(17) . . ?
H5B C5 H5A 109(2) . . ?
C7 C6 C5 110.26(18) . . ?
C7 C6 H6B 111.5(15) . . ?
C5 C6 H6B 108.4(15) . . ?
C7 C6 H6A 107.3(16) . . ?
C5 C6 H6A 113.0(17) . . ?
H6B C6 H6A 106(2) . . ?
O3 C7 O2 123.0(2) . . ?
O3 C7 C6 124.2(2) . . ?
O2 C7 C6 112.68(19) . . ?
C3 C8 H8C 113.8(17) . . ?
C3 C8 H8B 110.8(17) . . ?
H8C C8 H8B 110(2) . . ?
C3 C8 H8A 111.2(18) . . ?
H8C C8 H8A 106(2) . . ?
H8B C8 H8A 104(2) . . ?
C4 C9 C10 124.8(2) . . ?
C4 C9 H9 118.3(15) . . ?
C10 C9 H9 116.8(15) . . ?
O4 C10 N2 121.9(2) . . ?
O4 C10 C9 123.01(19) . . ?
N2 C10 C9 115.08(19) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_FO6807
_database_code_depnum_ccdc_archive 'CCDC 1904793'
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O6 S'
_chemical_formula_sum            'C15 H15 N O6 S'
_chemical_formula_weight         337.34

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.7698(4)
_cell_length_b                   9.8328(6)
_cell_length_c                   11.4487(7)
_cell_angle_alpha                68.144(3)
_cell_angle_beta                 73.035(3)
_cell_angle_gamma                76.069(3)
_cell_volume                     767.82(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6957
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.088
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6957
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3396
_reflns_number_gt                3006
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_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)+(0.0215P)²+0.6131P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3396
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 0.71091(6) 0.65080(5) 0.24756(4) 0.02263(13) Uani 1 1 d . . .
O1 O 0.59972(17) 0.93656(14) 0.37221(12) 0.0257(3) Uani 1 1 d . . .
O2 O 0.52734(17) 0.77053(14) 0.22878(11) 0.0229(3) Uani 1 1 d . . .
O3 O -0.1801(2) 0.7963(2) 0.78926(15) 0.0471(4) Uani 1 1 d . . .
O4 O 0.05081(17) 0.92658(15) 0.71683(12) 0.0261(3) Uani 1 1 d . . .
O5 O 0.70435(18) 0.59063(15) 0.38281(12) 0.0278(3) Uani 1 1 d . . .
O6 O 0.85748(18) 0.72543(16) 0.16054(14) 0.0327(3) Uani 1 1 d . . .
N1 N 0.3099(2) 0.89683(17) 0.49881(15) 0.0214(3) Uani 1 1 d . . .
H1N1 H 0.304(3) 0.938(3) 0.552(2) 0.037(6) Uiso 1 1 d . . .
C1 C 0.4583(2) 0.88553(19) 0.40098(16) 0.0202(4) Uani 1 1 d . . .
C2 C 0.4115(2) 0.79735(19) 0.33747(17) 0.0210(4) Uani 1 1 d . . .
C3 C 0.2476(2) 0.75741(19) 0.39595(17) 0.0218(4) Uani 1 1 d . . .
C4 C 0.1795(2) 0.81741(19) 0.50469(17) 0.0215(4) Uani 1 1 d . . .
C5 C 0.0232(3) 0.7919(2) 0.59303(18) 0.0246(4) Uani 1 1 d . . .
H5 H -0.047(3) 0.733(2) 0.584(2) 0.032(6) Uiso 1 1 d . . .
C6 C -0.0464(3) 0.8367(2) 0.70851(18) 0.0273(4) Uani 1 1 d . . .
C7 C -0.0112(3) 0.9683(2) 0.83298(19) 0.0288(4) Uani 1 1 d . . .
H7C H -0.142(3) 1.016(2) 0.842(2) 0.030(6) Uiso 1 1 d . . .
H7B H -0.004(3) 0.881(2) 0.909(2) 0.028(5) Uiso 1 1 d . . .
H7A H 0.072(3) 1.035(3) 0.825(2) 0.046(7) Uiso 1 1 d . . .
C8 C 0.1468(3) 0.6671(2) 0.3666(2) 0.0278(4) Uani 1 1 d . . .
H8C H 0.205(3) 0.653(3) 0.284(2) 0.037(6) Uiso 1 1 d . . .
H8B H 0.022(3) 0.714(3) 0.362(2) 0.040(6) Uiso 1 1 d . . .
H8A H 0.138(3) 0.572(3) 0.435(2) 0.043(7) Uiso 1 1 d . . .
C9 C 0.6776(2) 0.51883(19) 0.19110(17) 0.0210(4) Uani 1 1 d . . .
C10 C 0.5656(2) 0.4138(2) 0.27249(17) 0.0233(4) Uani 1 1 d . . .
H10 H 0.511(3) 0.413(2) 0.357(2) 0.030(6) Uiso 1 1 d . . .
C11 C 0.5405(3) 0.3103(2) 0.22621(18) 0.0239(4) Uani 1 1 d . . .
H11 H 0.467(3) 0.237(2) 0.282(2) 0.027(5) Uiso 1 1 d . . .
C12 C 0.6271(2) 0.3087(2) 0.10076(18) 0.0238(4) Uani 1 1 d . . .
C13 C 0.7371(3) 0.4160(2) 0.02200(18) 0.0263(4) Uani 1 1 d . . .
H13 H 0.798(3) 0.419(3) -0.068(2) 0.039(6) Uiso 1 1 d . . .
C14 C 0.7624(2) 0.5226(2) 0.06559(18) 0.0245(4) Uani 1 1 d . . .
H14 H 0.838(3) 0.595(2) 0.010(2) 0.030(6) Uiso 1 1 d . . .
C15 C 0.6016(3) 0.1933(2) 0.0533(2) 0.0296(4) Uani 1 1 d . . .
H15C H 0.621(4) 0.095(3) 0.111(3) 0.059(8) Uiso 1 1 d . . .
H15B H 0.681(4) 0.196(3) -0.027(3) 0.052(7) Uiso 1 1 d . . .
H15A H 0.475(4) 0.207(3) 0.043(3) 0.069(9) Uiso 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 O6 1.4226(14) . ?
S1 O5 1.4271(13) . ?
S1 O2 1.6274(13) . ?
S1 C9 1.7469(17) . ?
O1 C1 1.224(2) . ?
O2 C2 1.380(2) . ?
O3 C6 1.207(2) . ?
O4 C6 1.336(2) . ?
O4 C7 1.451(2) . ?
N1 C1 1.369(2) . ?
N1 C4 1.394(2) . ?
N1 H1N1 0.83(2) . ?
C1 C2 1.479(2) . ?
C2 C3 1.331(3) . ?
C3 C4 1.480(2) . ?
C3 C8 1.492(2) . ?
C4 C5 1.342(3) . ?
C5 C6 1.462(3) . ?
C5 H5 0.93(2) . ?
C7 H7C 1.01(2) . ?
C7 H7B 0.97(2) . ?
C7 H7A 0.98(3) . ?
C8 H8C 0.97(2) . ?
C8 H8B 0.98(2) . ?
C8 H8A 0.97(3) . ?
C9 C14 1.386(2) . ?
C9 C10 1.391(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.93(2) . ?
C11 C12 1.401(2) . ?
C11 H11 0.95(2) . ?
C12 C13 1.390(3) . ?
C12 C15 1.501(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.99(2) . ?
C14 H14 0.95(2) . ?
C15 H15C 0.95(3) . ?
C15 H15B 0.94(3) . ?
C15 H15A 0.99(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 S1 O5 120.63(9) . . ?
O6 S1 O2 105.72(8) . . ?
O5 S1 O2 107.11(7) . . ?
O6 S1 C9 109.73(8) . . ?
O5 S1 C9 110.67(8) . . ?
O2 S1 C9 100.99(7) . . ?
C2 O2 S1 117.70(11) . . ?
C6 O4 C7 115.32(15) . . ?
C1 N1 C4 110.57(15) . . ?
C1 N1 H1N1 124.2(16) . . ?
C4 N1 H1N1 125.0(16) . . ?
O1 C1 N1 127.71(16) . . ?
O1 C1 C2 127.25(16) . . ?
N1 C1 C2 105.04(14) . . ?
C3 C2 O2 127.79(16) . . ?
C3 C2 C1 111.02(15) . . ?
O2 C2 C1 121.13(15) . . ?
C2 C3 C4 106.04(15) . . ?
C2 C3 C8 129.63(17) . . ?
C4 C3 C8 124.31(17) . . ?
C5 C4 N1 128.35(17) . . ?
C5 C4 C3 124.38(16) . . ?
N1 C4 C3 107.22(15) . . ?
C4 C5 C6 127.76(17) . . ?
C4 C5 H5 117.0(13) . . ?
C6 C5 H5 115.1(13) . . ?
O3 C6 O4 122.93(18) . . ?
O3 C6 C5 122.93(18) . . ?
O4 C6 C5 114.14(16) . . ?
O4 C7 H7C 110.4(12) . . ?
O4 C7 H7B 110.3(13) . . ?
H7C C7 H7B 107.1(17) . . ?
O4 C7 H7A 105.8(14) . . ?
H7C C7 H7A 113.1(19) . . ?
H7B C7 H7A 110.0(19) . . ?
C3 C8 H8C 110.9(14) . . ?
C3 C8 H8B 112.1(14) . . ?
H8C C8 H8B 106.9(19) . . ?
C3 C8 H8A 110.1(14) . . ?
H8C C8 H8A 110.8(19) . . ?
H8B C8 H8A 105.8(19) . . ?
C14 C9 C10 121.68(16) . . ?
C14 C9 S1 118.96(14) . . ?
C10 C9 S1 119.35(13) . . ?
C11 C10 C9 118.61(17) . . ?
C11 C10 H10 121.2(13) . . ?
C9 C10 H10 120.2(13) . . ?
C10 C11 C12 121.29(18) . . ?
C10 C11 H11 118.6(13) . . ?
C12 C11 H11 120.1(13) . . ?
C13 C12 C11 118.46(17) . . ?
C13 C12 C15 121.04(17) . . ?
C11 C12 C15 120.50(18) . . ?
C12 C13 C14 121.37(17) . . ?
C12 C13 H13 120.5(13) . . ?
C14 C13 H13 118.1(14) . . ?
C9 C14 C13 118.58(18) . . ?
C9 C14 H14 121.6(13) . . ?
C13 C14 H14 119.8(13) . . ?
C12 C15 H15C 113.3(17) . . ?
C12 C15 H15B 111.4(16) . . ?
H15C C15 H15B 107(2) . . ?
C12 C15 H15A 111.9(17) . . ?
H15C C15 H15A 105(2) . . ?
H15B C15 H15A 108(2) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.053
