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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1004146'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 N O6 S'
_chemical_formula_weight         263.26

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.5868(4)
_cell_length_b                   6.1938(4)
_cell_length_c                   31.330(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1084.14(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3759
_cell_measurement_theta_min      3.3528
_cell_measurement_theta_max      27.8339

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.317
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            6562
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         27.839
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2575
_reflns_number_gt                2406
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'Bruker APEX II'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  ?

_refine_special_details          
; 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0267P)²+0.2757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2575
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0610
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1584(4) 0.1667(3) 0.15155(7) 0.0167(5) Uani 1 1 d . . . . .
H1A H 0.0439 0.0786 0.1348 0.020 Uiso 1 1 calc R U . . .
H1B H 0.1987 0.0888 0.1782 0.020 Uiso 1 1 calc R U . . .
C2 C 0.0545(4) 0.3882(3) 0.16131(6) 0.0127(4) Uani 1 1 d . . . . .
H2 H -0.1192 0.3728 0.1684 0.015 Uiso 1 1 calc R U . . .
C3 C -0.0637(4) 0.6734(3) 0.11127(6) 0.0111(4) Uani 1 1 d . . . . .
C4 C -0.0025(3) 0.7711(3) 0.06809(6) 0.0111(4) Uani 1 1 d . . . . .
H4 H 0.1583 0.8414 0.0699 0.013 Uiso 1 1 calc R U . . .
C5 C 0.0094(3) 0.5864(3) 0.03614(6) 0.0111(4) Uani 1 1 d . . . . .
H5 H 0.0301 0.6444 0.0066 0.013 Uiso 1 1 calc R U . . .
C6 C 0.2220(4) 0.4360(3) 0.04773(6) 0.0112(4) Uani 1 1 d . . . . .
H6 H 0.3629 0.4848 0.0306 0.013 Uiso 1 1 calc R U . . .
C7 C 0.2910(3) 0.4595(3) 0.09546(6) 0.0116(4) Uani 1 1 d . . . . .
H7 H 0.4053 0.5830 0.0981 0.014 Uiso 1 1 calc R U . . .
C8 C 0.1808(4) 0.5075(3) 0.19763(6) 0.0132(4) Uani 1 1 d . . . . .
C9 C 0.3001(4) 0.4833(4) 0.26944(6) 0.0229(5) Uani 1 1 d . . . . .
H9A H 0.4713 0.5034 0.2639 0.034 Uiso 1 1 calc R U . . .
H9B H 0.2790 0.3899 0.2944 0.034 Uiso 1 1 calc R U . . .
H9C H 0.2254 0.6237 0.2749 0.034 Uiso 1 1 calc R U . . .
N1 N 0.0789(3) 0.5079(3) 0.12176(5) 0.0108(3) Uani 1 1 d . . . . .
O3 O -0.2119(2) 0.4736(2) 0.03943(5) 0.0144(3) Uani 1 1 d . . . . .
O1 O -0.2365(2) 0.7369(2) 0.13211(4) 0.0135(3) Uani 1 1 d . . . . .
O2 O -0.1754(3) 0.9293(2) 0.05699(5) 0.0147(3) Uani 1 1 d . . . . .
O4 O 0.1705(3) 0.2217(2) 0.03529(4) 0.0135(3) Uani 1 1 d . . . . .
O5 O 0.2571(3) 0.6874(2) 0.19505(5) 0.0204(3) Uani 1 1 d . . . . .
O6 O 0.1882(3) 0.3835(2) 0.23249(4) 0.0188(3) Uani 1 1 d . . . . .
S1 S 0.42686(10) 0.22378(9) 0.12053(2) 0.01650(13) Uani 1 1 d . . . . .
H03 H -0.236(4) 0.411(4) 0.0162(8) 0.019(7) Uiso 1 1 d . . . . .
H04 H 0.038(5) 0.186(4) 0.0438(8) 0.034(8) Uiso 1 1 d . . . . .
H02 H -0.268(5) 0.937(5) 0.0768(9) 0.030(8) 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
C1 C2 1.520(3) . ?
C1 S1 1.822(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.451(2) . ?
C2 C8 1.529(3) . ?
C2 H2 1.0000 . ?
C3 O1 1.230(2) . ?
C3 N1 1.339(2) . ?
C3 C4 1.521(3) . ?
C4 O2 1.419(2) . ?
C4 C5 1.522(3) . ?
C4 H4 1.0000 . ?
C5 O3 1.424(2) . ?
C5 C6 1.552(3) . ?
C5 H5 1.0000 . ?
C6 O4 1.413(3) . ?
C6 C7 1.551(3) . ?
C6 H6 1.0000 . ?
C7 N1 1.474(2) . ?
C7 S1 1.823(2) . ?
C7 H7 1.0000 . ?
C8 O5 1.196(3) . ?
C8 O6 1.336(2) . ?
C9 O6 1.454(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O3 H03 0.84(3) . ?
O2 H02 0.81(3) . ?
O4 H04 0.82(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 104.27(14) . . ?
C2 C1 H1A 110.9 . . ?
S1 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
S1 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
N1 C2 C1 104.69(15) . . ?
N1 C2 C8 110.18(16) . . ?
C1 C2 C8 114.18(17) . . ?
N1 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C8 C2 H2 109.2 . . ?
O1 C3 N1 125.55(17) . . ?
O1 C3 C4 121.41(17) . . ?
N1 C3 C4 112.91(16) . . ?
O2 C4 C3 109.87(15) . . ?
O2 C4 C5 112.81(15) . . ?
C3 C4 C5 107.20(16) . . ?
O2 C4 H4 109.0 . . ?
C3 C4 H4 109.0 . . ?
C5 C4 H4 109.0 . . ?
O3 C5 C4 106.46(15) . . ?
O3 C5 C6 110.68(16) . . ?
C4 C5 C6 109.31(15) . . ?
O3 C5 H5 110.1 . . ?
C4 C5 H5 110.1 . . ?
C6 C5 H5 110.1 . . ?
O4 C6 C7 113.87(16) . . ?
O4 C6 C5 110.07(15) . . ?
C7 C6 C5 111.06(15) . . ?
O4 C6 H6 107.2 . . ?
C7 C6 H6 107.2 . . ?
C5 C6 H6 107.2 . . ?
N1 C7 C6 111.00(15) . . ?
N1 C7 S1 104.89(13) . . ?
C6 C7 S1 116.33(14) . . ?
N1 C7 H7 108.1 . . ?
C6 C7 H7 108.1 . . ?
S1 C7 H7 108.1 . . ?
O5 C8 O6 125.45(19) . . ?
O5 C8 C2 124.36(18) . . ?
O6 C8 C2 110.18(17) . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 N1 C2 123.03(16) . . ?
C3 N1 C7 119.79(16) . . ?
C2 N1 C7 116.68(16) . . ?
C5 O3 H03 107.8(17) . . ?
C4 O2 H02 107(2) . . ?
C6 O4 H04 111(2) . . ?
C8 O6 C9 114.86(17) . . ?
C1 S1 C7 92.43(9) . . ?

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
S1 C1 C2 N1 42.16(17) . . . . ?
S1 C1 C2 C8 -78.41(17) . . . . ?
O1 C3 C4 O2 -2.3(2) . . . . ?
N1 C3 C4 O2 173.80(15) . . . . ?
O1 C3 C4 C5 -125.18(19) . . . . ?
N1 C3 C4 C5 50.9(2) . . . . ?
O2 C4 C5 O3 -67.1(2) . . . . ?
C3 C4 C5 O3 54.00(19) . . . . ?
O2 C4 C5 C6 173.34(15) . . . . ?
C3 C4 C5 C6 -65.59(19) . . . . ?
O3 C5 C6 O4 32.8(2) . . . . ?
C4 C5 C6 O4 149.71(16) . . . . ?
O3 C5 C6 C7 -94.26(19) . . . . ?
C4 C5 C6 C7 22.7(2) . . . . ?
O4 C6 C7 N1 -92.5(2) . . . . ?
C5 C6 C7 N1 32.5(2) . . . . ?
O4 C6 C7 S1 27.3(2) . . . . ?
C5 C6 C7 S1 152.26(14) . . . . ?
N1 C2 C8 O5 10.2(3) . . . . ?
C1 C2 C8 O5 127.6(2) . . . . ?
N1 C2 C8 O6 -171.14(16) . . . . ?
C1 C2 C8 O6 -53.7(2) . . . . ?
O1 C3 N1 C2 -3.8(3) . . . . ?
C4 C3 N1 C2 -179.66(16) . . . . ?
O1 C3 N1 C7 -175.40(18) . . . . ?
C4 C3 N1 C7 8.7(2) . . . . ?
C1 C2 N1 C3 154.16(17) . . . . ?
C8 C2 N1 C3 -82.6(2) . . . . ?
C1 C2 N1 C7 -34.0(2) . . . . ?
C8 C2 N1 C7 89.2(2) . . . . ?
C6 C7 N1 C3 -52.7(2) . . . . ?
S1 C7 N1 C3 -179.14(14) . . . . ?
C6 C7 N1 C2 135.14(17) . . . . ?
S1 C7 N1 C2 8.73(19) . . . . ?
O5 C8 O6 C9 0.0(3) . . . . ?
C2 C8 O6 C9 -178.67(17) . . . . ?
C2 C1 S1 C7 -33.75(14) . . . . ?
N1 C7 S1 C1 15.30(13) . . . . ?
C6 C7 S1 C1 -107.74(15) . . . . ?

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
O3 H03 O4 0.84(3) 1.88(3) 2.716(2) 173(2) 2_455
O4 H04 O2 0.82(3) 2.03(3) 2.735(2) 144(3) 1_545
O2 H02 O1 0.81(3) 2.14(3) 2.660(2) 122(3) .
O4 H04 O3 0.82(3) 2.27(3) 2.649(2) 109(2) .
O2 H02 S1 0.81(3) 2.82(3) 3.4965(16) 143(3) 1_465

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1004472'
_audit_update_record             
;
2014-05-21 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 N4 O7 S'
_chemical_formula_weight         320.29

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'

_space_group_crystal_system      monoclin
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   23.8066(9)
_cell_length_b                   5.4476(2)
_cell_length_c                   10.6667(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.7660(10)
_cell_angle_gamma                90
_cell_volume                     1301.85(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.292
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11047
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.150
_diffrn_reflns_theta_max         27.917
_diffrn_reflns_theta_full        25.125
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3096
_reflns_number_gt                3014
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.5843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1318 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.008(19)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3096
_refine_ls_number_parameters     197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.40500(8) -0.0732(4) 0.13755(17) 0.0130(3) Uani 1 1 d . . . . .
H11 H 0.3947 -0.2480 0.1429 0.016 Uiso 1 1 calc R U . . .
H12 H 0.4322 -0.0594 0.0852 0.016 Uiso 1 1 calc R U . . .
C2 C 0.43315(8) 0.0389(3) 0.27713(17) 0.0116(3) Uani 1 1 d . . . . .
H2 H 0.4618 -0.0806 0.3367 0.014 Uiso 1 1 calc R U . . .
C3 C 0.38644(8) 0.0175(4) 0.45080(17) 0.0128(3) Uani 1 1 d . . . . .
C4 C 0.32767(8) 0.0104(4) 0.48006(17) 0.0123(3) Uani 1 1 d . . . . .
H4 H 0.3170 -0.1659 0.4855 0.015 Uiso 1 1 calc R U . . .
C5 C 0.27435(7) 0.1356(4) 0.37733(16) 0.0122(3) Uani 1 1 d . . . . .
H5 H 0.2806 0.3172 0.3860 0.015 Uiso 1 1 calc R U . . .
C6 C 0.27314(8) 0.0594(3) 0.23918(17) 0.0123(4) Uani 1 1 d . . . . .
H6 H 0.2364 0.1225 0.1690 0.015 Uiso 1 1 calc R U . . .
C7 C 0.32911(8) 0.1740(3) 0.22480(17) 0.0114(4) Uani 1 1 d . . . . .
H7 H 0.3278 0.3559 0.2364 0.014 Uiso 1 1 calc R U . . .
C8 C 0.46491(8) 0.2819(4) 0.27586(18) 0.0148(4) Uani 1 1 d . . . . .
C9 C 0.53827(10) 0.4735(5) 0.2078(3) 0.0285(5) Uani 1 1 d . . . . .
H91 H 0.5115 0.6016 0.1560 0.043 Uiso 1 1 calc R U . . .
H92 H 0.5680 0.4339 0.1661 0.043 Uiso 1 1 calc R U . . .
H93 H 0.5585 0.5324 0.2988 0.043 Uiso 1 1 calc R U . . .
N1 N 0.38275(6) 0.0765(3) 0.32399(14) 0.0115(3) Uani 1 1 d . . . . .
N2 N 0.33560(7) 0.1245(4) 0.61047(14) 0.0157(3) Uani 1 1 d . . . . .
N3 N 0.36262(7) 0.0001(3) 0.71071(15) 0.0147(3) Uani 1 1 d . . . . .
N4 N 0.38550(8) -0.0878(4) 0.81032(16) 0.0223(4) Uani 1 1 d . . . . .
O1 O 0.28960(6) -0.0265(3) -0.02008(13) 0.0165(3) Uani 1 1 d . . . . .
O2 O 0.35572(6) 0.3342(3) 0.01678(13) 0.0176(3) Uani 1 1 d . . . . .
O3 O 0.43288(6) -0.0404(3) 0.53628(13) 0.0193(3) Uani 1 1 d . . . . .
O4 O 0.22042(6) 0.0799(3) 0.39912(13) 0.0148(3) Uani 1 1 d . . . . .
O5 O 0.27513(6) -0.2016(3) 0.23690(14) 0.0144(3) Uani 1 1 d . . . . .
O6 O 0.45541(6) 0.4677(3) 0.32455(15) 0.0212(3) Uani 1 1 d . . . . .
O7 O 0.50399(6) 0.2558(3) 0.21158(15) 0.0200(3) Uani 1 1 d . . . . .
S1 S 0.33991(2) 0.10857(8) 0.06716(4) 0.01166(10) Uani 1 1 d . . . . .
H04 H 0.2124(11) -0.075(5) 0.384(2) 0.017 Uiso 1 1 d . U . . .
H05 H 0.2598(11) -0.246(5) 0.167(3) 0.017 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.538(2) . ?
C1 S1 1.7773(18) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 N1 1.462(2) . ?
C2 C8 1.527(3) . ?
C2 H2 1.0000 . ?
C3 O3 1.213(2) . ?
C3 N1 1.364(2) . ?
C3 C4 1.534(2) . ?
C4 N2 1.476(2) . ?
C4 C5 1.529(2) . ?
C4 H4 1.0000 . ?
C5 O4 1.4129(19) . ?
C5 C6 1.522(2) . ?
C5 H5 1.0000 . ?
C6 O5 1.423(2) . ?
C6 C7 1.526(2) . ?
C6 H6 1.0000 . ?
C7 N1 1.455(2) . ?
C7 S1 1.8201(17) . ?
C7 H7 1.0000 . ?
C8 O6 1.194(2) . ?
C8 O7 1.337(2) . ?
C9 O7 1.448(2) . ?
C9 H91 0.9800 . ?
C9 H92 0.9800 . ?
C9 H93 0.9800 . ?
N2 N3 1.245(2) . ?
N3 N4 1.124(2) . ?
O1 S1 1.4450(14) . ?
O2 S1 1.4417(14) . ?
O4 H04 0.87(3) . ?
O5 H05 0.75(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 102.70(12) . . ?
C2 C1 H11 111.2 . . ?
S1 C1 H11 111.2 . . ?
C2 C1 H12 111.2 . . ?
S1 C1 H12 111.2 . . ?
H11 C1 H12 109.1 . . ?
N1 C2 C8 110.36(15) . . ?
N1 C2 C1 104.33(14) . . ?
C8 C2 C1 113.01(15) . . ?
N1 C2 H2 109.7 . . ?
C8 C2 H2 109.7 . . ?
C1 C2 H2 109.7 . . ?
O3 C3 N1 122.92(16) . . ?
O3 C3 C4 120.18(16) . . ?
N1 C3 C4 116.79(15) . . ?
N2 C4 C5 107.35(15) . . ?
N2 C4 C3 110.26(15) . . ?
C5 C4 C3 115.87(14) . . ?
N2 C4 H4 107.7 . . ?
C5 C4 H4 107.7 . . ?
C3 C4 H4 107.7 . . ?
O4 C5 C6 112.33(14) . . ?
O4 C5 C4 111.52(14) . . ?
C6 C5 C4 108.16(15) . . ?
O4 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
O5 C6 C5 107.41(15) . . ?
O5 C6 C7 111.83(15) . . ?
C5 C6 C7 104.75(14) . . ?
O5 C6 H6 110.9 . . ?
C5 C6 H6 110.9 . . ?
C7 C6 H6 110.9 . . ?
N1 C7 C6 111.04(14) . . ?
N1 C7 S1 103.70(11) . . ?
C6 C7 S1 114.44(12) . . ?
N1 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
S1 C7 H7 109.2 . . ?
O6 C8 O7 125.49(18) . . ?
O6 C8 C2 124.32(16) . . ?
O7 C8 C2 110.19(16) . . ?
O7 C9 H91 109.5 . . ?
O7 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
O7 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
C3 N1 C7 123.59(14) . . ?
C3 N1 C2 121.41(14) . . ?
C7 N1 C2 114.98(13) . . ?
N3 N2 C4 116.38(17) . . ?
N4 N3 N2 171.1(2) . . ?
C5 O4 H04 109.3(16) . . ?
C6 O5 H05 109(2) . . ?
C8 O7 C9 115.07(17) . . ?
O2 S1 O1 117.27(8) . . ?
O2 S1 C1 109.41(9) . . ?
O1 S1 C1 113.75(9) . . ?
O2 S1 C7 108.27(8) . . ?
O1 S1 C7 110.46(8) . . ?
C1 S1 C7 95.41(8) . . ?

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
S1 C1 C2 N1 43.36(15) . . . . ?
S1 C1 C2 C8 -76.54(15) . . . . ?
O3 C3 C4 N2 45.7(2) . . . . ?
N1 C3 C4 N2 -138.17(17) . . . . ?
O3 C3 C4 C5 167.86(18) . . . . ?
N1 C3 C4 C5 -16.0(2) . . . . ?
N2 C4 C5 O4 -67.5(2) . . . . ?
C3 C4 C5 O4 168.83(16) . . . . ?
N2 C4 C5 C6 168.52(15) . . . . ?
C3 C4 C5 C6 44.8(2) . . . . ?
O4 C5 C6 O5 -70.95(19) . . . . ?
C4 C5 C6 O5 52.55(18) . . . . ?
O4 C5 C6 C7 170.00(15) . . . . ?
C4 C5 C6 C7 -66.49(18) . . . . ?
O5 C6 C7 N1 -53.79(19) . . . . ?
C5 C6 C7 N1 62.24(18) . . . . ?
O5 C6 C7 S1 63.18(18) . . . . ?
C5 C6 C7 S1 179.21(12) . . . . ?
N1 C2 C8 O6 10.2(2) . . . . ?
C1 C2 C8 O6 126.60(19) . . . . ?
N1 C2 C8 O7 -169.14(14) . . . . ?
C1 C2 C8 O7 -52.76(19) . . . . ?
O3 C3 N1 C7 -172.49(19) . . . . ?
C4 C3 N1 C7 11.5(3) . . . . ?
O3 C3 N1 C2 9.1(3) . . . . ?
C4 C3 N1 C2 -166.87(16) . . . . ?
C6 C7 N1 C3 -36.0(2) . . . . ?
S1 C7 N1 C3 -159.32(15) . . . . ?
C6 C7 N1 C2 142.51(16) . . . . ?
S1 C7 N1 C2 19.14(18) . . . . ?
C8 C2 N1 C3 -101.96(19) . . . . ?
C1 C2 N1 C3 136.37(17) . . . . ?
C8 C2 N1 C7 79.54(18) . . . . ?
C1 C2 N1 C7 -42.13(19) . . . . ?
C5 C4 N2 N3 157.21(15) . . . . ?
C3 C4 N2 N3 -75.7(2) . . . . ?
O6 C8 O7 C9 2.5(3) . . . . ?
C2 C8 O7 C9 -178.11(16) . . . . ?
C2 C1 S1 O2 81.61(13) . . . . ?
C2 C1 S1 O1 -145.09(11) . . . . ?
C2 C1 S1 C7 -29.93(13) . . . . ?
N1 C7 S1 O2 -104.59(12) . . . . ?
C6 C7 S1 O2 134.30(13) . . . . ?
N1 C7 S1 O1 125.75(12) . . . . ?
C6 C7 S1 O1 4.64(16) . . . . ?
N1 C7 S1 C1 7.91(13) . . . . ?
C6 C7 S1 C1 -113.20(14) . . . . ?

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
O4 H04 N2 0.87(3) 2.01(3) 2.802(2) 151(2) 4_546
O5 H05 O1 0.75(3) 2.62(3) 3.0300(19) 116(2) .
O4 H04 O5 0.87(3) 2.60(2) 2.9270(19) 103.8(19) .
O5 H05 O1 0.75(3) 2.22(3) 2.906(2) 152(3) 4_545

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1004498'
_audit_update_record             
;
2014-05-21 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H16 N2 O6 S'
_chemical_formula_weight         304.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.813(9)
_cell_length_b                   9.696(14)
_cell_length_c                   11.51(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.53(5)
_cell_angle_gamma                90
_cell_volume                     642.9(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    468
_cell_measurement_theta_min      1.6845
_cell_measurement_theta_max      21.9853

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.053
_exptl_absorpt_coefficient_mu    0.281
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5882
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            13989
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.757
_diffrn_reflns_theta_max         27.203
_diffrn_reflns_theta_full        25.125
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2826
_reflns_number_gt                2430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.993

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'Bruker APEX II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0764P)²+0.9782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2826
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.029
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.3651(2) 0.34215(15) 0.82648(13) 0.0229(4) Uani 1 1 d . . . . .
O2 O -0.2102(8) 0.5827(4) 0.5044(4) 0.0190(9) Uani 1 1 d . . . . .
O3 O 0.2217(7) 0.4528(4) 0.5833(4) 0.0180(9) Uani 1 1 d . . . . .
O1 O -0.2866(7) 0.1079(4) 0.6088(3) 0.0162(8) Uani 1 1 d . . . . .
O6 O -0.2642(7) 0.3091(4) 0.2938(3) 0.0214(10) Uani 1 1 d . . . . .
N2 N -0.4386(8) 0.3196(4) 0.4577(4) 0.0139(10) Uani 1 1 d . . . . .
H02 H -0.5691 0.3203 0.4918 0.021 Uiso 1 1 d R U . . .
O5 O -0.1657(7) 0.2110(4) 0.9326(3) 0.0215(10) Uani 1 1 d . . . . .
N1 N -0.0301(7) 0.2440(5) 0.7211(4) 0.0130(9) Uani 1 1 d . . . . .
C6 C 0.0524(10) 0.4834(5) 0.6591(5) 0.0156(11) Uani 1 1 d . . . . .
H6 H 0.0813 0.5779 0.6926 0.019 Uiso 1 1 calc R U . . .
C3 C -0.1894(10) 0.2208(6) 0.6251(5) 0.0156(12) Uani 1 1 d . . . . .
C4 C -0.2254(8) 0.3357(6) 0.5355(4) 0.0144(10) Uani 1 1 d . . . . .
H4 H -0.0981 0.3256 0.4855 0.017 Uiso 1 1 calc R U . . .
C5 C -0.1911(10) 0.4769(6) 0.5926(5) 0.0145(12) Uani 1 1 d . . . . .
H5 H -0.3086 0.4922 0.6475 0.017 Uiso 1 1 calc R U . . .
O4 O 0.0900(9) 0.0458(6) 0.9916(4) 0.0398(13) Uani 1 1 d . . . . .
C2 C 0.0731(10) 0.1308(6) 0.7927(5) 0.0163(12) Uani 1 1 d . . . . .
H2 H 0.0367 0.0414 0.7511 0.020 Uiso 1 1 calc R U . . .
C7 C 0.0692(9) 0.3789(5) 0.7581(5) 0.0152(12) Uani 1 1 d . . . . .
H7 H -0.0196 0.4159 0.8201 0.018 Uiso 1 1 calc R U . . .
C8 C -0.0019(11) 0.1241(6) 0.9166(5) 0.0215(13) Uani 1 1 d . . . . .
C10 C -0.4411(10) 0.3100(5) 0.3400(5) 0.0167(12) Uani 1 1 d . . . . .
C11 C -0.6770(10) 0.3002(6) 0.2678(5) 0.0206(13) Uani 1 1 d . . . . .
H11A H -0.6898 0.2124 0.2253 0.031 Uiso 1 1 calc R U . . .
H11B H -0.6965 0.3767 0.2117 0.031 Uiso 1 1 calc R U . . .
H11C H -0.7978 0.3052 0.3196 0.031 Uiso 1 1 calc R U . . .
C1 C 0.3330(10) 0.1574(6) 0.8052(6) 0.0201(13) Uani 1 1 d . . . . .
H1A H 0.3977 0.1280 0.7337 0.024 Uiso 1 1 calc R U . . .
H1B H 0.4139 0.1067 0.8733 0.024 Uiso 1 1 calc R U . . .
C9 C -0.2278(12) 0.2188(7) 1.0516(5) 0.0278(15) Uani 1 1 d . . . . .
H9A H -0.0880 0.2360 1.1071 0.042 Uiso 1 1 calc R U . . .
H9B H -0.2984 0.1314 1.0713 0.042 Uiso 1 1 calc R U . . .
H9C H -0.3387 0.2941 1.0562 0.042 Uiso 1 1 calc R U . . .
H03 H 0.193(10) 0.512(7) 0.515(5) 0.009(14) Uiso 1 1 d . . . . .
H06 H -0.340(13) 0.591(8) 0.480(6) 0.022(19) 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 C1 1.814(7) . ?
S1 C7 1.830(6) . ?
O2 C5 1.437(7) . ?
O2 H06 0.77(8) . ?
O3 C6 1.429(7) . ?
O3 H03 0.97(6) . ?
O1 C3 1.235(7) . ?
O6 C10 1.218(7) . ?
N2 C10 1.356(8) . ?
N2 C4 1.439(7) . ?
N2 H02 0.8982 . ?
O5 C8 1.303(8) . ?
O5 C9 1.463(8) . ?
N1 C3 1.363(8) . ?
N1 C2 1.453(7) . ?
N1 C7 1.470(7) . ?
C6 C5 1.519(8) . ?
C6 C7 1.519(8) . ?
C6 H6 1.0000 . ?
C3 C4 1.514(8) . ?
C4 C5 1.520(8) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
O4 C8 1.218(7) . ?
C2 C1 1.521(8) . ?
C2 C8 1.546(9) . ?
C2 H2 1.0000 . ?
C7 H7 1.0000 . ?
C10 C11 1.510(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C7 93.4(3) . . ?
C5 O2 H06 108(5) . . ?
C6 O3 H03 108(4) . . ?
C10 N2 C4 121.6(5) . . ?
C10 N2 H02 122.5 . . ?
C4 N2 H02 115.8 . . ?
C8 O5 C9 116.1(5) . . ?
C3 N1 C2 121.4(5) . . ?
C3 N1 C7 125.5(4) . . ?
C2 N1 C7 112.9(4) . . ?
O3 C6 C5 110.8(5) . . ?
O3 C6 C7 109.8(4) . . ?
C5 C6 C7 108.3(4) . . ?
O3 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
C7 C6 H6 109.3 . . ?
O1 C3 N1 121.2(5) . . ?
O1 C3 C4 122.0(5) . . ?
N1 C3 C4 116.7(5) . . ?
N2 C4 C3 112.0(5) . . ?
N2 C4 C5 114.9(5) . . ?
C3 C4 C5 111.7(5) . . ?
N2 C4 H4 105.8 . . ?
C3 C4 H4 105.8 . . ?
C5 C4 H4 105.8 . . ?
O2 C5 C6 107.8(4) . . ?
O2 C5 C4 110.1(5) . . ?
C6 C5 C4 108.4(4) . . ?
O2 C5 H5 110.2 . . ?
C6 C5 H5 110.2 . . ?
C4 C5 H5 110.2 . . ?
N1 C2 C1 104.9(5) . . ?
N1 C2 C8 114.2(5) . . ?
C1 C2 C8 108.5(5) . . ?
N1 C2 H2 109.7 . . ?
C1 C2 H2 109.7 . . ?
C8 C2 H2 109.7 . . ?
N1 C7 C6 113.1(4) . . ?
N1 C7 S1 105.2(4) . . ?
C6 C7 S1 114.6(4) . . ?
N1 C7 H7 107.9 . . ?
C6 C7 H7 107.9 . . ?
S1 C7 H7 107.9 . . ?
O4 C8 O5 124.3(6) . . ?
O4 C8 C2 121.9(5) . . ?
O5 C8 C2 113.7(5) . . ?
O6 C10 N2 122.5(5) . . ?
O6 C10 C11 121.2(5) . . ?
N2 C10 C11 116.4(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C1 S1 105.3(4) . . ?
C2 C1 H1A 110.7 . . ?
S1 C1 H1A 110.7 . . ?
C2 C1 H1B 110.7 . . ?
S1 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C3 O1 14.9(8) . . . . ?
C7 N1 C3 O1 -170.3(5) . . . . ?
C2 N1 C3 C4 -160.2(5) . . . . ?
C7 N1 C3 C4 14.6(8) . . . . ?
C10 N2 C4 C3 -121.8(5) . . . . ?
C10 N2 C4 C5 109.4(5) . . . . ?
O1 C3 C4 N2 22.1(7) . . . . ?
N1 C3 C4 N2 -162.8(5) . . . . ?
O1 C3 C4 C5 152.6(5) . . . . ?
N1 C3 C4 C5 -32.4(6) . . . . ?
O3 C6 C5 O2 -63.5(5) . . . . ?
C7 C6 C5 O2 176.0(4) . . . . ?
O3 C6 C5 C4 55.6(6) . . . . ?
C7 C6 C5 C4 -64.8(6) . . . . ?
N2 C4 C5 O2 -55.2(6) . . . . ?
C3 C4 C5 O2 175.9(4) . . . . ?
N2 C4 C5 C6 -172.9(4) . . . . ?
C3 C4 C5 C6 58.2(6) . . . . ?
C3 N1 C2 C1 130.1(5) . . . . ?
C7 N1 C2 C1 -45.3(6) . . . . ?
C3 N1 C2 C8 -111.3(6) . . . . ?
C7 N1 C2 C8 73.3(6) . . . . ?
C3 N1 C7 C6 -21.8(7) . . . . ?
C2 N1 C7 C6 153.4(5) . . . . ?
C3 N1 C7 S1 -147.6(4) . . . . ?
C2 N1 C7 S1 27.6(5) . . . . ?
O3 C6 C7 N1 -75.4(6) . . . . ?
C5 C6 C7 N1 45.7(6) . . . . ?
O3 C6 C7 S1 45.2(6) . . . . ?
C5 C6 C7 S1 166.3(4) . . . . ?
C1 S1 C7 N1 -1.4(4) . . . . ?
C1 S1 C7 C6 -126.3(4) . . . . ?
C9 O5 C8 O4 4.3(9) . . . . ?
C9 O5 C8 C2 -174.2(5) . . . . ?
N1 C2 C8 O4 -171.1(6) . . . . ?
C1 C2 C8 O4 -54.6(8) . . . . ?
N1 C2 C8 O5 7.4(7) . . . . ?
C1 C2 C8 O5 124.0(6) . . . . ?
C4 N2 C10 O6 2.9(8) . . . . ?
C4 N2 C10 C11 -177.1(5) . . . . ?
N1 C2 C1 S1 40.5(5) . . . . ?
C8 C2 C1 S1 -81.9(5) . . . . ?
C7 S1 C1 C2 -22.5(4) . . . . ?

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
N2 H02 O2 0.90 2.64 3.141(7) 116.1 2_446
N2 H02 O3 0.90 2.14 2.899(7) 141.9 1_455
O3 H03 O1 0.97(6) 1.84(6) 2.739(7) 153(5) 2_556
O2 H06 O1 0.77(8) 2.28(8) 3.052(7) 175(7) 2_456

_refine_diff_density_max         1.145
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1004616'
_audit_update_record             
;
2014-05-22 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H12 N4 O5 S'
_chemical_formula_sum            'C9 H12 N4 O5 S'
_chemical_formula_weight         288.29

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   6.2462(4)
_cell_length_b                   9.5487(7)
_cell_length_c                   20.1585(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1202.32(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3780
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.96

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      1.587
_exptl_crystal_density_method    calculated
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.107
_exptl_absorpt_coefficient_mu    0.294
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5959
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            8429
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.939
_diffrn_reflns_theta_max         27.042
_diffrn_reflns_theta_full        25.125
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2613
_reflns_number_gt                2328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'BRUKER APEX II'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'Bruker APEX II'
_computing_structure_solution    'BRUKER APEX II'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.2382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 901 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.07(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2613
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3916(5) 0.6328(3) 0.04981(14) 0.0178(6) Uani 1 1 d . . . . .
H1A H 0.2827 0.5757 0.0265 0.021 Uiso 1 1 calc R U . . .
H1B H 0.4636 0.6941 0.0171 0.021 Uiso 1 1 calc R U . . .
C2 C 0.5547(4) 0.5387(3) 0.08493(13) 0.0149(6) Uani 1 1 d . . . . .
H2 H 0.4855 0.4491 0.0991 0.018 Uiso 1 1 calc R U . . .
C3 C 0.5318(4) 0.7547(3) 0.15195(12) 0.0152(6) Uani 1 1 d . . . . .
H3 H 0.6153 0.8252 0.1260 0.018 Uiso 1 1 calc R U . . .
C4 C 0.5328(4) 0.7974(3) 0.22443(13) 0.0158(6) Uani 1 1 d . . . . .
H4 H 0.4800 0.8958 0.2286 0.019 Uiso 1 1 calc R U . . .
C5 C 0.7630(5) 0.7896(3) 0.24871(12) 0.0161(6) Uani 1 1 d . . . . .
H5 H 0.8508 0.8555 0.2214 0.019 Uiso 1 1 calc R U . . .
C6 C 0.8589(4) 0.6405(3) 0.24093(13) 0.0165(6) Uani 1 1 d . . . . .
H6 H 1.0156 0.6519 0.2324 0.020 Uiso 1 1 calc R U . . .
C7 C 0.7677(4) 0.5553(3) 0.18394(13) 0.0139(5) Uani 1 1 d . . . . .
C8 C 0.7441(5) 0.5087(3) 0.03948(12) 0.0144(5) Uani 1 1 d . . . . .
C9 C 0.8761(6) 0.3650(4) -0.04570(16) 0.0284(8) Uani 1 1 d . . . . .
H9A H 0.9017 0.4470 -0.0738 0.043 Uiso 1 1 calc R U . . .
H9B H 0.8316 0.2859 -0.0734 0.043 Uiso 1 1 calc R U . . .
H9C H 1.0080 0.3407 -0.0220 0.043 Uiso 1 1 calc R U . . .
N1 N 0.6300(4) 0.6167(3) 0.14276(11) 0.0133(5) Uani 1 1 d . . . . .
N2 N 0.8365(4) 0.5536(3) 0.30092(12) 0.0198(6) Uani 1 1 d . . . . .
N3 N 0.9836(4) 0.5710(3) 0.34179(12) 0.0211(6) Uani 1 1 d . . . . .
N4 N 1.1056(4) 0.5734(3) 0.38316(14) 0.0317(7) Uani 1 1 d . . . . .
O1 O 0.7075(3) 0.3970(2) 0.00227(10) 0.0211(5) Uani 1 1 d . . . . .
O2 O 0.9014(3) 0.5809(2) 0.03634(10) 0.0201(5) Uani 1 1 d . . . . .
O3 O 0.8262(3) 0.4331(2) 0.17459(10) 0.0174(5) Uani 1 1 d . . . . .
O4 O 0.7694(4) 0.8358(2) 0.31538(10) 0.0208(5) Uani 1 1 d . . . . .
O5 O 0.3977(3) 0.7071(2) 0.26140(10) 0.0200(5) Uani 1 1 d . . . . .
S1 S 0.26896(10) 0.73611(8) 0.11482(3) 0.01814(18) Uani 1 1 d . . . . .
H04 H 0.890(6) 0.881(4) 0.3186(19) 0.033(10) Uiso 1 1 d . . . . .
H05 H 0.350(6) 0.757(5) 0.287(2) 0.041(12) 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
C1 C2 1.532(4) . ?
C1 S1 1.810(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.461(3) . ?
C2 C8 1.524(4) . ?
C2 H2 1.0000 . ?
C3 N1 1.465(4) . ?
C3 C4 1.517(4) . ?
C3 S1 1.813(3) . ?
C3 H3 1.0000 . ?
C4 O5 1.418(3) . ?
C4 C5 1.521(4) . ?
C4 H4 1.0000 . ?
C5 O4 1.415(3) . ?
C5 C6 1.552(4) . ?
C5 H5 1.0000 . ?
C6 N2 1.473(4) . ?
C6 C7 1.519(4) . ?
C6 H6 1.0000 . ?
C7 O3 1.237(3) . ?
C7 N1 1.331(3) . ?
C8 O2 1.202(4) . ?
C8 O1 1.324(3) . ?
C9 O1 1.462(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N2 N3 1.245(3) . ?
N3 N4 1.130(3) . ?
O4 H04 0.87(4) . ?
O5 H05 0.77(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 105.45(18) . . ?
C2 C1 H1A 110.7 . . ?
S1 C1 H1A 110.7 . . ?
C2 C1 H1B 110.7 . . ?
S1 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
N1 C2 C8 109.0(2) . . ?
N1 C2 C1 106.5(2) . . ?
C8 C2 C1 110.4(2) . . ?
N1 C2 H2 110.3 . . ?
C8 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
N1 C3 C4 111.2(2) . . ?
N1 C3 S1 103.82(17) . . ?
C4 C3 S1 115.31(18) . . ?
N1 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
S1 C3 H3 108.8 . . ?
O5 C4 C3 109.9(2) . . ?
O5 C4 C5 111.3(2) . . ?
C3 C4 C5 107.5(2) . . ?
O5 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
O4 C5 C4 108.5(2) . . ?
O4 C5 C6 111.8(2) . . ?
C4 C5 C6 112.2(2) . . ?
O4 C5 H5 108.1 . . ?
C4 C5 H5 108.1 . . ?
C6 C5 H5 108.1 . . ?
N2 C6 C7 106.5(2) . . ?
N2 C6 C5 113.4(2) . . ?
C7 C6 C5 115.0(2) . . ?
N2 C6 H6 107.2 . . ?
C7 C6 H6 107.2 . . ?
C5 C6 H6 107.2 . . ?
O3 C7 N1 120.7(3) . . ?
O3 C7 C6 120.7(2) . . ?
N1 C7 C6 118.6(2) . . ?
O2 C8 O1 125.0(3) . . ?
O2 C8 C2 124.0(2) . . ?
O1 C8 C2 111.0(3) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 N1 C2 118.8(2) . . ?
C7 N1 C3 126.0(2) . . ?
C2 N1 C3 115.1(2) . . ?
N3 N2 C6 113.5(2) . . ?
N4 N3 N2 171.4(3) . . ?
C8 O1 C9 114.7(2) . . ?
C5 O4 H04 104(3) . . ?
C4 O5 H05 102(3) . . ?
C1 S1 C3 88.21(12) . . ?

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
S1 C1 C2 N1 -30.7(3) . . . . ?
S1 C1 C2 C8 -148.9(2) . . . . ?
N1 C3 C4 O5 -66.1(3) . . . . ?
S1 C3 C4 O5 51.7(3) . . . . ?
N1 C3 C4 C5 55.2(3) . . . . ?
S1 C3 C4 C5 173.01(18) . . . . ?
O5 C4 C5 O4 -62.5(3) . . . . ?
C3 C4 C5 O4 177.1(2) . . . . ?
O5 C4 C5 C6 61.5(3) . . . . ?
C3 C4 C5 C6 -58.9(3) . . . . ?
O4 C5 C6 N2 28.6(3) . . . . ?
C4 C5 C6 N2 -93.5(3) . . . . ?
O4 C5 C6 C7 151.5(2) . . . . ?
C4 C5 C6 C7 29.3(3) . . . . ?
N2 C6 C7 O3 -50.7(3) . . . . ?
C5 C6 C7 O3 -177.2(2) . . . . ?
N2 C6 C7 N1 131.9(2) . . . . ?
C5 C6 C7 N1 5.4(4) . . . . ?
N1 C2 C8 O2 -27.5(4) . . . . ?
C1 C2 C8 O2 89.1(3) . . . . ?
N1 C2 C8 O1 155.3(2) . . . . ?
C1 C2 C8 O1 -88.1(3) . . . . ?
O3 C7 N1 C2 -2.1(4) . . . . ?
C6 C7 N1 C2 175.3(2) . . . . ?
O3 C7 N1 C3 173.3(2) . . . . ?
C6 C7 N1 C3 -9.3(4) . . . . ?
C8 C2 N1 C7 -63.8(3) . . . . ?
C1 C2 N1 C7 177.1(2) . . . . ?
C8 C2 N1 C3 120.3(2) . . . . ?
C1 C2 N1 C3 1.2(3) . . . . ?
C4 C3 N1 C7 -22.4(4) . . . . ?
S1 C3 N1 C7 -147.0(2) . . . . ?
C4 C3 N1 C2 153.2(2) . . . . ?
S1 C3 N1 C2 28.6(3) . . . . ?
C7 C6 N2 N3 146.8(2) . . . . ?
C5 C6 N2 N3 -85.8(3) . . . . ?
O2 C8 O1 C9 -0.5(4) . . . . ?
C2 C8 O1 C9 176.7(2) . . . . ?
C2 C1 S1 C3 41.0(2) . . . . ?
N1 C3 S1 C1 -39.29(18) . . . . ?
C4 C3 S1 C1 -161.2(2) . . . . ?

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
O4 H04 O3 0.87(4) 1.85(4) 2.699(3) 166(4) 3_755
O5 H05 O3 0.77(4) 2.15(5) 2.878(3) 158(4) 3_655

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_an23_0m
_database_code_depnum_ccdc_archive 'CCDC 1004644'
_audit_update_record             
;
2014-05-22 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 B N2 O7 S'
_chemical_formula_weight         406.21

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'
B B 0.0013 0.0007 '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   'P 21 21 21'

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

_cell_length_a                   6.4782(3)
_cell_length_b                   9.8389(4)
_cell_length_c                   28.4710(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1814.69(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    133
_cell_measurement_theta_min      3.8189
_cell_measurement_theta_max      21.5532

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.033
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8948
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17673
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         27.20
_reflns_number_total             4032
_reflns_number_gt                3578
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Instrument Service v3.0.28'
_computing_cell_refinement       'APEX2 v2013.4-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  ?

_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 > 2σ(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
_chemical_absolute_configuration syn
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0259P)²+0.8243P] 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   0.00(7)
_refine_ls_number_reflns         4032
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 -0.03951(8) 0.94911(5) 0.030819(18) 0.01377(11) Uani 1 1 d . . .
O1 O 0.3322(3) 0.84908(15) -0.05773(5) 0.0190(3) Uani 1 1 d . . .
O2 O 0.1226(2) 1.00532(14) 0.12845(5) 0.0138(3) Uani 1 1 d . . .
O3 O 0.9999(2) 0.64609(15) 0.27143(5) 0.0190(3) Uani 1 1 d . . .
O4 O 0.4120(2) 1.07123(15) -0.05761(5) 0.0160(3) Uani 1 1 d . . .
O5 O 0.6329(2) 1.16986(15) 0.04211(5) 0.0148(3) Uani 1 1 d . . .
O6 O 0.5116(2) 1.38142(16) 0.09583(5) 0.0172(4) Uani 1 1 d . . .
O7 O 0.3769(2) 1.15576(15) 0.14896(5) 0.0149(3) Uani 1 1 d . . .
N1 N 0.3069(3) 1.08416(17) 0.03781(6) 0.0108(4) Uani 1 1 d . . .
N2 N 0.8896(3) 0.85583(17) 0.24808(6) 0.0144(4) Uani 1 1 d . . .
H4 H 0.9230 0.9425 0.2488 0.017 Uiso 1 1 calc R . .
C1 C 0.3338(4) 0.8486(2) -0.10865(7) 0.0250(5) Uani 1 1 d . . .
H8 H 0.2164 0.9015 -0.1204 0.038 Uiso 1 1 calc R . .
H1 H 0.3233 0.7549 -0.1200 0.038 Uiso 1 1 calc R . .
H9 H 0.4627 0.8891 -0.1200 0.038 Uiso 1 1 calc R . .
C2 C 0.3697(3) 0.9678(2) -0.03722(7) 0.0127(4) Uani 1 1 d . . .
C3 C 0.3622(3) 0.9545(2) 0.01639(7) 0.0118(4) Uani 1 1 d . . .
H10 H 0.5010 0.9258 0.0281 0.014 Uiso 1 1 calc R . .
C4 C 0.0885(3) 1.1029(2) 0.05068(7) 0.0102(4) Uani 1 1 d . . .
H16 H 0.0311 1.1830 0.0334 0.012 Uiso 1 1 calc R . .
C5 C 0.0720(3) 1.1276(2) 0.10355(7) 0.0123(4) Uani 1 1 d . . .
H17 H -0.0702 1.1589 0.1120 0.015 Uiso 1 1 calc R . .
C6 C 0.4183(3) 0.9077(2) 0.17718(7) 0.0140(4) Uani 1 1 d . . .
C7 C 0.6054(3) 0.9289(2) 0.20031(7) 0.0136(4) Uani 1 1 d . . .
H18 H 0.6655 1.0170 0.2001 0.016 Uiso 1 1 calc R . .
C8 C 0.7058(3) 0.8238(2) 0.22368(7) 0.0127(4) Uani 1 1 d . . .
C9 C 1.0214(3) 0.7704(2) 0.27066(7) 0.0140(4) Uani 1 1 d . . .
C10 C 1.1973(3) 0.8398(2) 0.29546(8) 0.0176(5) Uani 1 1 d . . .
H3 H 1.2493 0.7808 0.3205 0.026 Uiso 1 1 calc R . .
H19 H 1.1488 0.9256 0.3090 0.026 Uiso 1 1 calc R . .
H2 H 1.3083 0.8583 0.2730 0.026 Uiso 1 1 calc R . .
C11 C 0.3358(4) 0.7766(2) 0.17675(7) 0.0162(5) Uani 1 1 d . . .
H7 H 0.2097 0.7598 0.1607 0.019 Uiso 1 1 calc R . .
C12 C 0.4353(3) 0.6712(2) 0.19934(7) 0.0169(5) Uani 1 1 d . . .
H6 H 0.3779 0.5824 0.1984 0.020 Uiso 1 1 calc R . .
C13 C 0.6186(3) 0.6939(2) 0.22340(7) 0.0150(4) Uani 1 1 d . . .
H5 H 0.6845 0.6214 0.2396 0.018 Uiso 1 1 calc R . .
C14 C 0.2004(3) 0.8543(2) 0.03383(8) 0.0150(4) Uani 1 1 d . . .
H12 H 0.2300 0.8255 0.0665 0.018 Uiso 1 1 calc R . .
H11 H 0.1949 0.7728 0.0135 0.018 Uiso 1 1 calc R . .
C15 C 0.4479(3) 1.1778(2) 0.05072(6) 0.0113(4) Uani 1 1 d . . .
C16 C 0.3571(3) 1.2943(2) 0.07905(7) 0.0117(4) Uani 1 1 d . . .
H14 H 0.2606 1.3472 0.0586 0.014 Uiso 1 1 calc R . .
C17 C 0.2358(3) 1.2332(2) 0.12004(7) 0.0126(4) Uani 1 1 d . . .
H15 H 0.1688 1.3067 0.1389 0.015 Uiso 1 1 calc R . .
B1 B 0.3041(4) 1.0258(2) 0.15197(8) 0.0135(5) Uani 1 1 d . . .
H13 H 0.608(4) 1.365(3) 0.0851(9) 0.020 Uiso 1 1 d . . .


_geom_special_details            
; 
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell s.u.'s are taken 
 into account individually in the estimation of s.u.'s in distances, angles 
 and torsion angles; correlations between s.u.'s in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C14 1.814(2) . ?
S1 C4 1.816(2) . ?
O1 C2 1.329(2) . ?
O1 C1 1.450(3) . ?
O2 B1 1.368(3) . ?
O2 C5 1.434(2) . ?
O3 C9 1.231(3) . ?
O4 C2 1.203(2) . ?
O5 C15 1.225(2) . ?
O6 C16 1.402(2) . ?
O6 H13 0.71(3) . ?
O7 B1 1.365(3) . ?
O7 C17 1.447(2) . ?
N1 C15 1.349(3) . ?
N1 C3 1.459(3) . ?
N1 C4 1.473(2) . ?
N2 C9 1.360(3) . ?
N2 C8 1.414(3) . ?
N2 H4 0.8800 . ?
C1 H8 0.9800 . ?
C1 H1 0.9800 . ?
C1 H9 0.9800 . ?
C2 C3 1.533(3) . ?
C3 C14 1.522(3) . ?
C3 H10 1.0000 . ?
C4 C5 1.528(3) . ?
C4 H16 1.0000 . ?
C5 C17 1.558(3) . ?
C5 H17 1.0000 . ?
C6 C7 1.395(3) . ?
C6 C11 1.396(3) . ?
C6 B1 1.554(3) . ?
C7 C8 1.391(3) . ?
C7 H18 0.9500 . ?
C8 C13 1.398(3) . ?
C9 C10 1.504(3) . ?
C10 H3 0.9800 . ?
C10 H19 0.9800 . ?
C10 H2 0.9800 . ?
C11 C12 1.381(3) . ?
C11 H7 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H6 0.9500 . ?
C13 H5 0.9500 . ?
C14 H12 0.9900 . ?
C14 H11 0.9900 . ?
C15 C16 1.520(3) . ?
C16 C17 1.530(3) . ?
C16 H14 1.0000 . ?
C17 H15 1.0000 . ?

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
C14 S1 C4 91.30(9) . . ?
C2 O1 C1 116.16(17) . . ?
B1 O2 C5 108.34(16) . . ?
C16 O6 H13 110(2) . . ?
B1 O7 C17 108.09(16) . . ?
C15 N1 C3 123.02(17) . . ?
C15 N1 C4 119.82(16) . . ?
C3 N1 C4 116.72(16) . . ?
C9 N2 C8 128.55(18) . . ?
C9 N2 H4 115.7 . . ?
C8 N2 H4 115.7 . . ?
O1 C1 H8 109.5 . . ?
O1 C1 H1 109.5 . . ?
H8 C1 H1 109.5 . . ?
O1 C1 H9 109.5 . . ?
H8 C1 H9 109.5 . . ?
H1 C1 H9 109.5 . . ?
O4 C2 O1 124.99(19) . . ?
O4 C2 C3 124.08(18) . . ?
O1 C2 C3 110.88(16) . . ?
N1 C3 C14 105.12(16) . . ?
N1 C3 C2 110.43(16) . . ?
C14 C3 C2 113.72(17) . . ?
N1 C3 H10 109.1 . . ?
C14 C3 H10 109.1 . . ?
C2 C3 H10 109.1 . . ?
N1 C4 C5 109.41(16) . . ?
N1 C4 S1 104.86(13) . . ?
C5 C4 S1 114.01(14) . . ?
N1 C4 H16 109.5 . . ?
C5 C4 H16 109.5 . . ?
S1 C4 H16 109.5 . . ?
O2 C5 C4 109.72(16) . . ?
O2 C5 C17 104.77(15) . . ?
C4 C5 C17 110.78(16) . . ?
O2 C5 H17 110.5 . . ?
C4 C5 H17 110.5 . . ?
C17 C5 H17 110.5 . . ?
C7 C6 C11 118.37(19) . . ?
C7 C6 B1 121.34(19) . . ?
C11 C6 B1 120.29(19) . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H18 119.3 . . ?
C6 C7 H18 119.3 . . ?
C7 C8 C13 119.22(19) . . ?
C7 C8 N2 117.58(19) . . ?
C13 C8 N2 123.16(19) . . ?
O3 C9 N2 123.5(2) . . ?
O3 C9 C10 121.91(19) . . ?
N2 C9 C10 114.63(18) . . ?
C9 C10 H3 109.5 . . ?
C9 C10 H19 109.5 . . ?
H3 C10 H19 109.5 . . ?
C9 C10 H2 109.5 . . ?
H3 C10 H2 109.5 . . ?
H19 C10 H2 109.5 . . ?
C12 C11 C6 120.7(2) . . ?
C12 C11 H7 119.6 . . ?
C6 C11 H7 119.6 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H6 119.7 . . ?
C13 C12 H6 119.7 . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 H5 120.2 . . ?
C8 C13 H5 120.2 . . ?
C3 C14 S1 103.97(14) . . ?
C3 C14 H12 111.0 . . ?
S1 C14 H12 111.0 . . ?
C3 C14 H11 111.0 . . ?
S1 C14 H11 111.0 . . ?
H12 C14 H11 109.0 . . ?
O5 C15 N1 124.37(19) . . ?
O5 C15 C16 122.18(19) . . ?
N1 C15 C16 113.42(17) . . ?
O6 C16 C15 111.45(17) . . ?
O6 C16 C17 110.31(16) . . ?
C15 C16 C17 107.90(16) . . ?
O6 C16 H14 109.0 . . ?
C15 C16 H14 109.0 . . ?
C17 C16 H14 109.0 . . ?
O7 C17 C16 108.44(16) . . ?
O7 C17 C5 104.51(15) . . ?
C16 C17 C5 112.48(16) . . ?
O7 C17 H15 110.4 . . ?
C16 C17 H15 110.4 . . ?
C5 C17 H15 110.4 . . ?
O7 B1 O2 113.84(19) . . ?
O7 B1 C6 124.4(2) . . ?
O2 B1 C6 121.69(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 O4 -3.1(3) . . . . ?
C1 O1 C2 C3 179.66(18) . . . . ?
C15 N1 C3 C14 146.88(18) . . . . ?
C4 N1 C3 C14 -25.5(2) . . . . ?
C15 N1 C3 C2 -90.1(2) . . . . ?
C4 N1 C3 C2 97.58(19) . . . . ?
O4 C2 C3 N1 29.2(3) . . . . ?
O1 C2 C3 N1 -153.50(17) . . . . ?
O4 C2 C3 C14 147.1(2) . . . . ?
O1 C2 C3 C14 -35.6(2) . . . . ?
C15 N1 C4 C5 -52.8(2) . . . . ?
C3 N1 C4 C5 119.78(17) . . . . ?
C15 N1 C4 S1 -175.50(14) . . . . ?
C3 N1 C4 S1 -2.9(2) . . . . ?
C14 S1 C4 N1 24.24(14) . . . . ?
C14 S1 C4 C5 -95.40(15) . . . . ?
B1 O2 C5 C4 112.30(18) . . . . ?
B1 O2 C5 C17 -6.7(2) . . . . ?
N1 C4 C5 O2 -69.3(2) . . . . ?
S1 C4 C5 O2 47.75(19) . . . . ?
N1 C4 C5 C17 45.9(2) . . . . ?
S1 C4 C5 C17 162.95(14) . . . . ?
C11 C6 C7 C8 -1.9(3) . . . . ?
B1 C6 C7 C8 178.70(19) . . . . ?
C6 C7 C8 C13 0.9(3) . . . . ?
C6 C7 C8 N2 -177.00(18) . . . . ?
C9 N2 C8 C7 -175.2(2) . . . . ?
C9 N2 C8 C13 7.0(3) . . . . ?
C8 N2 C9 O3 2.7(3) . . . . ?
C8 N2 C9 C10 -176.72(19) . . . . ?
C7 C6 C11 C12 1.1(3) . . . . ?
B1 C6 C11 C12 -179.5(2) . . . . ?
C6 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C8 -1.7(3) . . . . ?
C7 C8 C13 C12 0.9(3) . . . . ?
N2 C8 C13 C12 178.67(18) . . . . ?
N1 C3 C14 S1 41.36(17) . . . . ?
C2 C3 C14 S1 -79.55(18) . . . . ?
C4 S1 C14 C3 -38.62(14) . . . . ?
C3 N1 C15 O5 6.9(3) . . . . ?
C4 N1 C15 O5 179.05(19) . . . . ?
C3 N1 C15 C16 -170.94(17) . . . . ?
C4 N1 C15 C16 1.2(2) . . . . ?
O5 C15 C16 O6 -4.1(3) . . . . ?
N1 C15 C16 O6 173.81(16) . . . . ?
O5 C15 C16 C17 -125.4(2) . . . . ?
N1 C15 C16 C17 52.6(2) . . . . ?
B1 O7 C17 C16 -123.29(18) . . . . ?
B1 O7 C17 C5 -3.1(2) . . . . ?
O6 C16 C17 O7 -60.9(2) . . . . ?
C15 C16 C17 O7 61.1(2) . . . . ?
O6 C16 C17 C5 -175.97(16) . . . . ?
C15 C16 C17 C5 -54.0(2) . . . . ?
O2 C5 C17 O7 5.94(19) . . . . ?
C4 C5 C17 O7 -112.31(17) . . . . ?
O2 C5 C17 C16 123.37(17) . . . . ?
C4 C5 C17 C16 5.1(2) . . . . ?
C17 O7 B1 O2 -1.1(2) . . . . ?
C17 O7 B1 C6 175.78(19) . . . . ?
C5 O2 B1 O7 5.2(2) . . . . ?
C5 O2 B1 C6 -171.75(18) . . . . ?
C7 C6 B1 O7 2.1(3) . . . . ?
C11 C6 B1 O7 -177.3(2) . . . . ?
C7 C6 B1 O2 178.72(19) . . . . ?
C11 C6 B1 O2 -0.7(3) . . . . ?

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
O6 H13 O4 0.71(3) 2.21(3) 2.851(2) 150(3) 2_575
O6 H13 O5 0.71(3) 2.28(3) 2.700(2) 119(3) .
N2 H4 O3 0.88 2.14 2.996(2) 163.2 3_755
C1 H8 O6 0.98 2.61 3.398(3) 137.6 2_475
C3 H10 S1 1.00 2.99 3.898(2) 152.1 1_655
C4 H16 O4 1.00 2.63 3.409(2) 134.8 2_475
C7 H18 O3 0.95 2.64 3.428(3) 140.7 3_755
C13 H5 O3 0.95 2.25 2.862(3) 121.5 .
C14 H12 O2 0.99 2.59 3.117(3) 113.0 .
C16 H14 O4 1.00 2.40 3.231(2) 140.4 2_475

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.13
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052
