# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1884429'
loop_
_audit_author_name
_audit_author_address
'M. Minas da Piedade'
;CQE ISTand DQB FCUL
Portugal
;
_audit_update_record             
;
2019-02-15 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 N O4'
_chemical_formula_weight         157.13

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.4942(6)
_cell_length_b                   16.396(2)
_cell_length_c                   9.0283(12)
_cell_angle_alpha                90
_cell_angle_beta                 89.977(7)
_cell_angle_gamma                90
_cell_volume                     665.26(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1412
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      ?23.51

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6235
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3430
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.359
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.800
_diffrn_measured_fraction_theta_full 0.779
_diffrn_reflns_Laue_measured_fraction_max 0.800
_diffrn_reflns_Laue_measured_fraction_full 0.779
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_point_group_measured_fraction_full 0.779
_reflns_number_total             1098
_reflns_number_gt                610
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    Mercury
_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)+(0.0218P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1098
_refine_ls_number_parameters     128
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   0.761
_refine_ls_restrained_S_all      0.764
_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
O1W O 0.7835(5) 0.41945(10) 0.91467(19) 0.0414(5) Uani 1 1 d D . . . .
O1 O 0.1219(4) 0.59288(9) 0.46547(16) 0.0426(5) Uani 1 1 d D . . . .
O2 O 0.7070(4) 0.83580(9) 0.67577(17) 0.0434(5) Uani 1 1 d . . . . .
O3 O 0.9827(4) 0.77386(9) 0.84519(17) 0.0492(5) Uani 1 1 d . . . . .
N1 N 0.6060(5) 0.55411(11) 0.76674(18) 0.0330(5) Uani 1 1 d D . . . .
C2 C 0.6443(5) 0.69314(13) 0.7144(2) 0.0287(5) Uani 1 1 d . . . . .
C4 C 0.3176(6) 0.60756(12) 0.5728(2) 0.0296(5) Uani 1 1 d . . . . .
C5 C 0.4052(5) 0.54278(14) 0.6597(2) 0.0326(6) Uani 1 1 d D . . . .
C1 C 0.7266(6) 0.62628(14) 0.7964(2) 0.0315(6) Uani 1 1 d . . . . .
C6 C 0.7861(5) 0.77475(13) 0.7469(2) 0.0338(6) Uani 1 1 d . . . . .
C3 C 0.4403(5) 0.68350(13) 0.6020(2) 0.0299(5) Uani 1 1 d D . . . .
H1W H 0.662(7) 0.3840(16) 0.895(3) 0.058(10) Uiso 1 1 d . . . . .
H2W H 0.947(6) 0.3981(19) 0.869(4) 0.107(15) Uiso 1 1 d D . . . .
H1N H 0.655(5) 0.5070(11) 0.818(2) 0.045(7) Uiso 1 1 d D . . . .
H3 H 0.373(5) 0.7283(10) 0.5449(19) 0.041(7) Uiso 1 1 d D . . . .
H1 H 0.872(6) 0.6290(13) 0.877(2) 0.043(7) Uiso 1 1 d . . . . .
H5 H 0.323(5) 0.4897(10) 0.651(2) 0.031(6) Uiso 1 1 d D . . . .
H1O H 0.066(8) 0.6360(14) 0.412(3) 0.101(12) Uiso 1 1 d 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
O1W H1W 0.82(3) . ?
O1W H2W 0.914(19) . ?
O1 C4 1.331(3) . ?
O1 H1O 0.892(18) . ?
O2 C6 1.241(2) . ?
O3 C6 1.253(3) . ?
N1 C1 1.329(3) . ?
N1 C5 1.336(3) . ?
N1 H1N 0.927(16) . ?
C2 C1 1.374(3) . ?
C2 C3 1.377(3) . ?
C2 C6 1.511(3) . ?
C4 C5 1.378(3) . ?
C4 C3 1.387(3) . ?
C5 H5 0.949(15) . ?
C1 H1 0.98(2) . ?
C3 H3 0.947(15) . ?

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
H1W O1W H2W 100(3) . . ?
C4 O1 H1O 116(2) . . ?
C1 N1 C5 123.06(19) . . ?
C1 N1 H1N 123.0(14) . . ?
C5 N1 H1N 113.9(14) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 C6 119.23(19) . . ?
C3 C2 C6 121.72(18) . . ?
O1 C4 C5 117.65(19) . . ?
O1 C4 C3 124.29(19) . . ?
C5 C4 C3 118.1(2) . . ?
N1 C5 C4 119.9(2) . . ?
N1 C5 H5 116.6(12) . . ?
C4 C5 H5 123.5(13) . . ?
N1 C1 C2 119.5(2) . . ?
N1 C1 H1 117.5(13) . . ?
C2 C1 H1 123.0(13) . . ?
O2 C6 O3 125.3(2) . . ?
O2 C6 C2 119.53(19) . . ?
O3 C6 C2 115.15(19) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 121.7(13) . . ?
C4 C3 H3 117.7(13) . . ?

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 N1 C5 C4 0.9(4) . . . . ?
O1 C4 C5 N1 178.6(2) . . . . ?
C3 C4 C5 N1 -1.0(3) . . . . ?
C5 N1 C1 C2 -0.1(3) . . . . ?
C3 C2 C1 N1 -0.6(3) . . . . ?
C6 C2 C1 N1 -179.0(2) . . . . ?
C1 C2 C6 O2 -178.1(2) . . . . ?
C3 C2 C6 O2 3.6(3) . . . . ?
C1 C2 C6 O3 3.0(3) . . . . ?
C3 C2 C6 O3 -175.3(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C6 C2 C3 C4 178.8(2) . . . . ?
O1 C4 C3 C2 -179.3(2) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1884431'
loop_
_audit_author_name
_audit_author_address
'M. Minas da Piedade'
;CQE ISTand DQB FCUL
Portugal
;
_audit_update_record             
;
2019-02-15 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 N O4 S'
_chemical_formula_weight         217.24

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.2351(3)
_cell_length_b                   22.4779(13)
_cell_length_c                   8.4174(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.301(4)
_cell_angle_gamma                90
_cell_volume                     987.72(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    167(2)
_cell_measurement_reflns_used    4554
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      30.47

_exptl_crystal_description       paralelipedic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      167(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14192
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.590
_diffrn_reflns_theta_max         30.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3008
_reflns_number_gt                2342
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    Mercury
_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)+(0.0574P)²+0.1897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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
H1 H 0.095(4) 0.7901(9) 0.401(2) 0.021(5) Uiso 1 1 d . . . . .
H5 H -0.249(3) 0.6466(8) 0.525(2) 0.015(4) Uiso 1 1 d . . . . .
H3 H 0.334(3) 0.6344(8) 0.232(2) 0.012(4) Uiso 1 1 d . . . . .
H3O H 0.698(5) 0.7419(12) 0.076(3) 0.060(8) Uiso 1 1 d . . . . .
H1O H 0.077(5) 0.5553(10) 0.314(3) 0.034(6) Uiso 1 1 d . . . . .
H7A H 0.740(4) 0.4637(10) 0.152(3) 0.035(6) Uiso 1 1 d . . . . .
H8B H 0.338(4) 0.3731(11) 0.052(3) 0.045(7) Uiso 1 1 d . . . . .
H8A H 0.382(4) 0.4301(10) -0.047(3) 0.036(6) Uiso 1 1 d . . . . .
H7C H 0.719(5) 0.4692(12) 0.338(3) 0.055(8) Uiso 1 1 d . . . . .
H7B H 0.708(5) 0.4061(12) 0.264(3) 0.048(7) Uiso 1 1 d . . . . .
H8C H 0.098(5) 0.4149(12) 0.004(3) 0.053(8) Uiso 1 1 d . . . . .
S1 S 0.32846(8) 0.45022(2) 0.21874(5) 0.01808(12) Uani 1 1 d . . . . .
O3 O 0.5805(2) 0.71663(5) 0.13228(14) 0.0157(2) Uani 1 1 d . . . . .
O2 O 0.4596(2) 0.80517(5) 0.22302(15) 0.0204(3) Uani 1 1 d . . . . .
O1 O -0.0102(3) 0.57033(6) 0.37822(17) 0.0248(3) Uani 1 1 d . . . . .
O4 O 0.2682(2) 0.51486(5) 0.17973(16) 0.0237(3) Uani 1 1 d . . . . .
N1 N -0.0978(2) 0.72396(6) 0.47389(16) 0.0143(3) Uani 1 1 d . . . . .
C5 C -0.1208(3) 0.66488(7) 0.46730(19) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.2426(3) 0.71841(7) 0.30137(18) 0.0124(3) Uani 1 1 d . . . . .
C6 C 0.4387(3) 0.75133(7) 0.21462(18) 0.0128(3) Uani 1 1 d . . . . .
C3 C 0.2195(3) 0.65691(7) 0.29391(19) 0.0143(3) Uani 1 1 d . . . . .
C4 C 0.0326(3) 0.62930(7) 0.3780(2) 0.0158(3) Uani 1 1 d . . . . .
C8 C 0.2856(4) 0.41168(9) 0.0342(2) 0.0269(4) Uani 1 1 d . . . . .
C1 C 0.0794(3) 0.75050(7) 0.39159(19) 0.0134(3) Uani 1 1 d . . . . .
C7 C 0.6689(4) 0.44601(9) 0.2454(3) 0.0311(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.5176(12) . ?
S1 C8 1.778(2) . ?
S1 C7 1.782(2) . ?
O3 C6 1.3103(18) . ?
O3 H3O 0.98(3) . ?
O2 C6 1.2167(19) . ?
O1 C4 1.3443(19) . ?
O1 H1O 0.81(2) . ?
N1 C5 1.334(2) . ?
N1 C1 1.3392(19) . ?
C5 C4 1.393(2) . ?
C5 H5 0.950(19) . ?
C2 C1 1.387(2) . ?
C2 C3 1.389(2) . ?
C2 C6 1.499(2) . ?
C3 C4 1.395(2) . ?
C3 H3 0.963(18) . ?
C8 H8B 0.92(2) . ?
C8 H8A 0.97(2) . ?
C8 H8C 1.00(3) . ?
C1 H1 0.90(2) . ?
C7 H7A 0.98(2) . ?
C7 H7C 0.95(3) . ?
C7 H7B 0.93(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
O4 S1 C8 105.48(9) . . ?
O4 S1 C7 105.53(9) . . ?
C8 S1 C7 98.26(11) . . ?
C6 O3 H3O 108.0(15) . . ?
C4 O1 H1O 108.1(16) . . ?
C5 N1 C1 119.06(13) . . ?
N1 C5 C4 122.69(14) . . ?
N1 C5 H5 118.3(11) . . ?
C4 C5 H5 119.0(11) . . ?
C1 C2 C3 119.17(14) . . ?
C1 C2 C6 118.84(14) . . ?
C3 C2 C6 121.99(13) . . ?
O2 C6 O3 124.80(13) . . ?
O2 C6 C2 121.64(13) . . ?
O3 C6 C2 113.55(13) . . ?
C2 C3 C4 118.80(14) . . ?
C2 C3 H3 119.4(11) . . ?
C4 C3 H3 121.7(11) . . ?
O1 C4 C5 117.54(14) . . ?
O1 C4 C3 124.23(14) . . ?
C5 C4 C3 118.23(14) . . ?
S1 C8 H8B 107.7(16) . . ?
S1 C8 H8A 111.6(14) . . ?
H8B C8 H8A 111(2) . . ?
S1 C8 H8C 104.1(15) . . ?
H8B C8 H8C 113(2) . . ?
H8A C8 H8C 110(2) . . ?
N1 C1 C2 122.04(14) . . ?
N1 C1 H1 117.3(13) . . ?
C2 C1 H1 120.6(13) . . ?
S1 C7 H7A 108.4(14) . . ?
S1 C7 H7C 106.5(16) . . ?
H7A C7 H7C 109(2) . . ?
S1 C7 H7B 106.2(16) . . ?
H7A C7 H7B 116(2) . . ?
H7C C7 H7B 110(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C5 C4 0.0(2) . . . . ?
C1 C2 C6 O2 0.8(2) . . . . ?
C3 C2 C6 O2 -179.23(15) . . . . ?
C1 C2 C6 O3 -179.43(13) . . . . ?
C3 C2 C6 O3 0.5(2) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C6 C2 C3 C4 179.91(14) . . . . ?
N1 C5 C4 O1 -178.99(15) . . . . ?
N1 C5 C4 C3 0.8(2) . . . . ?
C2 C3 C4 O1 179.06(15) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C5 N1 C1 C2 -0.9(2) . . . . ?
C3 C2 C1 N1 1.0(2) . . . . ?
C6 C2 C1 N1 -179.07(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
_geom_hbond_publ_flag
C5 H5 O2 0.950(19) 2.582(19) 3.2589(19) 128.4(14) 4_476 yes
O1 H1O S1 0.81(2) 2.85(2) 3.5485(14) 147(2) . yes
O1 H1O O4 0.81(2) 1.81(3) 2.6146(18) 175(2) . yes
C8 H8B O3 0.92(2) 2.60(3) 3.305(2) 134(2) 3_665 yes
C8 H8B O2 0.92(2) 2.60(3) 3.358(2) 141(2) 2_645 yes
C8 H8A O4 0.97(2) 2.54(2) 3.472(3) 161.2(19) 3_665 yes
C7 H7B O2 0.93(3) 2.44(3) 3.251(2) 146(2) 2_645 yes

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1884430'
loop_
_audit_author_name
_audit_author_address
'M. Minas da Piedade'
;CQE ISTand DQB FCUL
Portugal
;
_audit_update_record             
;
2019-02-15 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 N O4'
_chemical_formula_weight         157.13

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.50390(10)
_cell_length_b                   16.3890(6)
_cell_length_c                   8.8561(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.271(2)
_cell_angle_gamma                90
_cell_volume                     653.55(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    167(2)
_cell_measurement_reflns_used    1880
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.20

_exptl_crystal_description       paralelipedic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   psi-scans
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      167(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5329
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.485
_diffrn_reflns_theta_max         26.418
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1340
_reflns_number_gt                1127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    Mercury
_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)+(0.0549P)²+0.0750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1340
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
H3 H 0.378(3) 0.2717(9) 0.4538(16) 0.014(3) Uiso 1 1 d . . . . .
H1N H 0.659(3) 0.4979(10) 0.1768(17) 0.025(4) Uiso 1 1 d . . . . .
H5 H 0.332(3) 0.5138(10) 0.3512(17) 0.021(4) Uiso 1 1 d . . . . .
H1 H 0.869(4) 0.3730(10) 0.122(2) 0.028(4) Uiso 1 1 d . . . . .
H1O H 0.068(5) 0.3573(14) 0.577(2) 0.054(6) Uiso 1 1 d . . . . .
H1W H 0.649700 0.620203 0.101501 0.051(6) Uiso 1 1 d . . . . .
H2W H 0.959700 0.606900 0.121403 0.055(6) Uiso 1 1 d . . . . .
O1 O 0.1162(2) 0.40725(6) 0.53149(12) 0.0246(3) Uani 1 1 d . . . . .
O2 O 0.9789(2) 0.22693(6) 0.15017(12) 0.0272(3) Uani 1 1 d . . . . .
N1 N 0.6083(2) 0.44781(7) 0.23153(13) 0.0195(3) Uani 1 1 d . . . . .
O1W O 0.7898(2) 0.58274(6) 0.08691(11) 0.0234(3) Uani 1 1 d . . . . .
O3 O 0.6967(2) 0.16395(6) 0.31786(12) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.4350(3) 0.31603(8) 0.39434(15) 0.0179(3) Uani 1 1 d . . . . .
C5 C 0.4058(3) 0.45873(8) 0.33812(16) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.7275(3) 0.37492(8) 0.20105(16) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.3129(3) 0.39302(8) 0.42447(15) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.7810(3) 0.22567(8) 0.24761(16) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.6405(3) 0.30725(8) 0.28212(15) 0.0177(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 C4 1.3324(17) . ?
O1 H1O 0.94(2) . ?
O2 C6 1.2544(16) . ?
N1 C5 1.3391(17) . ?
N1 C1 1.3396(18) . ?
N1 H1N 0.984(17) . ?
O1W H1W 0.8919(9) . ?
O1W H2W 0.9084(10) . ?
O3 C6 1.2509(16) . ?
C3 C2 1.3806(19) . ?
C3 C4 1.4043(19) . ?
C3 H3 0.936(15) . ?
C5 C4 1.3904(19) . ?
C5 H5 0.970(16) . ?
C1 C2 1.3826(18) . ?
C1 H1 0.957(18) . ?
C6 C2 1.5133(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
C4 O1 H1O 108.5(13) . . ?
C5 N1 C1 122.93(12) . . ?
C5 N1 H1N 114.0(9) . . ?
C1 N1 H1N 123.1(9) . . ?
H1W O1W H2W 104.16(9) . . ?
C2 C3 C4 120.13(12) . . ?
C2 C3 H3 121.3(9) . . ?
C4 C3 H3 118.5(9) . . ?
N1 C5 C4 120.13(12) . . ?
N1 C5 H5 116.7(9) . . ?
C4 C5 H5 123.2(9) . . ?
N1 C1 C2 119.42(13) . . ?
N1 C1 H1 117.0(10) . . ?
C2 C1 H1 123.6(10) . . ?
O1 C4 C5 117.93(12) . . ?
O1 C4 C3 124.18(12) . . ?
C5 C4 C3 117.88(12) . . ?
O3 C6 O2 125.70(12) . . ?
O3 C6 C2 118.76(12) . . ?
O2 C6 C2 115.53(11) . . ?
C3 C2 C1 119.50(12) . . ?
C3 C2 C6 121.84(12) . . ?
C1 C2 C6 118.64(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
C1 N1 C5 C4 0.9(2) . . . . ?
C5 N1 C1 C2 0.0(2) . . . . ?
N1 C5 C4 O1 178.48(11) . . . . ?
N1 C5 C4 C3 -0.9(2) . . . . ?
C2 C3 C4 O1 -179.24(12) . . . . ?
C2 C3 C4 C5 0.05(19) . . . . ?
C4 C3 C2 C1 0.8(2) . . . . ?
C4 C3 C2 C6 179.05(12) . . . . ?
N1 C1 C2 C3 -0.8(2) . . . . ?
N1 C1 C2 C6 -179.12(12) . . . . ?
O3 C6 C2 C3 3.7(2) . . . . ?
O2 C6 C2 C3 -175.35(12) . . . . ?
O3 C6 C2 C1 -178.04(13) . . . . ?
O2 C6 C2 C1 2.96(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1W 0.984(17) 1.712(17) 2.6918(14) 173.5(14) . yes
C5 H5 O1 0.970(16) 2.631(15) 3.4357(16) 140.6(11) 3_566 yes
C1 H1 O1W 0.957(18) 2.538(18) 3.4579(17) 161.3(14) 3_765 yes
O1W H1W O3 0.8919(9) 1.8730(9) 2.7142(13) 156.47(7) 2_655 yes
O1W H2W O3 0.9084(10) 1.8764(10) 2.7827(14) 175.34(7) 2_755 yes
O1 H1O O2 0.94(2) 1.58(2) 2.5203(13) 178(2) 4_466 yes

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1884432'
loop_
_audit_author_name
_audit_author_address
'M. Minas da Piedade'
;CQE ISTand DQB FCUL
Portugal
;
_audit_update_record             
;
2019-02-15 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 N O4 S'
_chemical_formula_weight         217.24

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.2638(7)
_cell_length_b                   22.580(3)
_cell_length_c                   8.5353(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.269(7)
_cell_angle_gamma                90
_cell_volume                     1012.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6285
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      28.17

_exptl_crystal_description       paralelipipedic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.308
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23477
_diffrn_reflns_av_unetI/netI     0.2139
_diffrn_reflns_av_R_equivalents  0.1359
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         30.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3069
_reflns_number_gt                1446
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    Mercury
_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)+(0.1335P)²] 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_number_reflns         3069
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1740
_refine_ls_R_factor_gt           0.0742
_refine_ls_wR_factor_ref         0.2378
_refine_ls_wR_factor_gt          0.2101
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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
H1O H 0.038(7) 0.5564(17) 0.310(4) 0.039(10) Uiso 1 1 d . . . . .
H3 H 0.642(7) 0.7339(18) 0.086(4) 0.043(12) Uiso 1 1 d . . . . .
S1 S 0.31521(18) 0.45010(5) 0.22579(11) 0.0522(3) Uani 1 1 d . . . . .
O3 O 0.5573(4) 0.71544(11) 0.1168(2) 0.0341(5) Uani 1 1 d . . . . .
O2 O 0.4410(4) 0.80342(11) 0.2050(3) 0.0456(6) Uani 1 1 d . . . . .
N1 N -0.1154(4) 0.72499(12) 0.4571(2) 0.0316(6) Uani 1 1 d . . . . .
C5 C -0.1357(5) 0.66697(15) 0.4536(3) 0.0351(7) Uani 1 1 d . . . . .
H5 H -0.257691 0.649342 0.512943 0.042 Uiso 1 1 calc R U . . .
C2 C 0.2252(5) 0.71787(13) 0.2858(3) 0.0256(6) Uani 1 1 d . . . . .
C6 C 0.4197(5) 0.75059(14) 0.1992(3) 0.0285(6) Uani 1 1 d . . . . .
O1 O -0.0274(6) 0.57218(12) 0.3698(4) 0.0566(7) Uani 1 1 d . . . . .
C3 C 0.2013(5) 0.65734(14) 0.2824(3) 0.0315(6) Uani 1 1 d . . . . .
H3A H 0.309002 0.634433 0.224538 0.038 Uiso 1 1 calc R U . . .
O4 O 0.2609(5) 0.51443(12) 0.1852(3) 0.0618(8) Uani 1 1 d . . . . .
C4 C 0.0138(5) 0.63077(15) 0.3668(3) 0.0349(7) Uani 1 1 d . . . . .
C1 C 0.0608(5) 0.75115(14) 0.3746(3) 0.0284(6) Uani 1 1 d . . . . .
H1 H 0.074794 0.792209 0.376140 0.034 Uiso 1 1 calc R U . . .
C7 C 0.6473(11) 0.4469(3) 0.2648(10) 0.126(3) Uani 1 1 d . . . . .
H7A H 0.696127 0.407011 0.291678 0.189 Uiso 1 1 calc R U . . .
H7B H 0.731498 0.459060 0.173343 0.189 Uiso 1 1 calc R U . . .
H7C H 0.695139 0.472746 0.350733 0.189 Uiso 1 1 calc R U . . .
C8 C 0.2910(11) 0.4120(2) 0.0494(6) 0.0840(15) Uani 1 1 d . . . . .
H8A H 0.323808 0.370680 0.068267 0.126 Uiso 1 1 calc R U . . .
H8B H 0.122654 0.416746 0.001666 0.126 Uiso 1 1 calc R U . . .
H8C H 0.413053 0.427336 -0.019423 0.126 Uiso 1 1 calc R 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
S1 O4 1.517(3) . ?
S1 C8 1.733(5) . ?
S1 C7 1.762(5) . ?
O3 C6 1.307(3) . ?
O3 H3 0.67(4) . ?
O2 C6 1.199(4) . ?
N1 C5 1.315(4) . ?
N1 C1 1.334(3) . ?
C5 C4 1.379(4) . ?
C5 H5 0.9300 . ?
C2 C3 1.373(4) . ?
C2 C1 1.401(4) . ?
C2 C6 1.492(4) . ?
O1 C4 1.341(4) . ?
O1 H1O 0.72(4) . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9300 . ?
C1 H1 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 C8 105.9(2) . . ?
O4 S1 C7 104.8(2) . . ?
C8 S1 C7 99.6(3) . . ?
C6 O3 H3 104(3) . . ?
C5 N1 C1 119.2(2) . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 C6 123.2(2) . . ?
C1 C2 C6 117.7(3) . . ?
O2 C6 O3 125.0(3) . . ?
O2 C6 C2 122.5(2) . . ?
O3 C6 C2 112.5(3) . . ?
C4 O1 H1O 113(3) . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
O1 C4 C5 118.5(3) . . ?
O1 C4 C3 123.8(3) . . ?
C5 C4 C3 117.8(3) . . ?
N1 C1 C2 121.2(3) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         1.494
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.085

