# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mdq012_0m
_database_code_depnum_ccdc_archive 'CCDC 2215968'
loop_
_audit_author_name
_audit_author_address
'Justin Newman'
;Merck and Co, Inc
United States of America
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2022-12-07 downloaded from the CCDC.
;
_audit_creation_date             2022-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H14 N O2, C7 H7 O3 S, 2(H2 O)'
_chemical_formula_sum            'C13 H25 N O7 S'
_chemical_formula_weight         339.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9459(9)
_cell_length_b                   13.5525(12)
_cell_length_c                   15.5352(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1672.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4421
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.428
_cell_measurement_theta_min      4.326
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    2.022
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0854 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.8951.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9594
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.514
_diffrn_reflns_theta_max         66.514
_diffrn_reflns_theta_min         4.329
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed-tube microsource X-ray generator'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2778
_reflns_number_total             2943
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1103 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+0.0294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O2W(H2WA), O1W(H1WA,H1WB)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.1604(3) 0.42089(16) -0.06582(15) 0.0383(5) Uani 1 1 d . . . . .
C2 C 1.2911(3) 0.49529(19) -0.03792(17) 0.0453(5) Uani 1 1 d . . . . .
C3 C 1.3565(4) 0.46930(18) 0.05102(18) 0.0438(6) Uani 1 1 d . . . . .
C4 C 1.4170(3) 0.36281(19) 0.05187(16) 0.0394(5) Uani 1 1 d . . . . .
C5 C 1.2811(4) 0.29359(18) 0.01918(16) 0.0411(5) Uani 1 1 d . . . . .
C6 C 1.0954(3) 0.4380(2) -0.15558(17) 0.0444(5) Uani 1 1 d . . . . .
C7 C 0.8537(5) 0.6987(2) -0.07729(19) 0.0577(7) Uani 1 1 d . . . . .
C8 C 0.7827(4) 0.6054(2) -0.08248(18) 0.0544(7) Uani 1 1 d . . . . .
C9 C 0.7795(4) 0.5432(2) -0.01202(17) 0.0451(6) Uani 1 1 d . . . . .
C10 C 0.8451(3) 0.57487(18) 0.06564(16) 0.0415(5) Uani 1 1 d . . . . .
C11 C 0.9131(5) 0.6687(2) 0.0727(2) 0.0576(7) Uani 1 1 d . . . . .
C12 C 0.9178(6) 0.7289(2) 0.0009(2) 0.0660(9) Uani 1 1 d . . . . .
C13 C 0.8624(9) 0.7654(4) -0.1549(3) 0.0881(14) Uani 1 1 d . . . . .
N1 N 1.4677(4) 0.33276(19) 0.14048(16) 0.0478(5) Uani 1 1 d . . . . .
O1 O 1.2297(2) 0.32263(11) -0.06498(10) 0.0390(4) Uani 1 1 d . . . . .
O2 O 0.9581(3) 0.37348(16) -0.17002(14) 0.0538(5) Uani 1 1 d . . . . .
O3 O 0.9814(3) 0.52020(15) 0.20946(14) 0.0565(5) Uani 1 1 d . . . . .
O4 O 0.6788(3) 0.5156(2) 0.19891(12) 0.0659(6) Uani 1 1 d . . . . .
O5 O 0.8404(4) 0.39591(15) 0.12339(14) 0.0640(6) Uani 1 1 d . . . . .
S1 S 0.83718(8) 0.49544(4) 0.15629(3) 0.04226(18) Uani 1 1 d . . . . .
O2W O 0.8067(3) 0.8541(2) 0.24996(16) 0.0680(6) Uani 1 1 d . . . . .
H2WA H 0.862570 0.805189 0.268793 0.102 Uiso 1 1 d G . . . .
O1W O 0.9745(4) 0.6917(2) 0.3142(2) 0.0837(9) Uani 1 1 d . . . . .
H1WA H 1.071561 0.710175 0.330602 0.126 Uiso 1 1 d G . . . .
H1WB H 0.985409 0.628790 0.282990 0.126 Uiso 1 1 d G . . . .
H2A H 1.385(4) 0.495(2) -0.0837(19) 0.050(8) Uiso 1 1 d . . . . .
H5A H 1.181(4) 0.296(2) 0.0582(18) 0.038(7) Uiso 1 1 d . . . . .
H3A H 1.271(4) 0.479(2) 0.0935(17) 0.039(7) Uiso 1 1 d . . . . .
H6A H 1.188(4) 0.428(2) -0.198(2) 0.048(8) Uiso 1 1 d . . . . .
H6B H 1.067(4) 0.505(2) -0.1586(18) 0.047(7) Uiso 1 1 d . . . . .
H2B H 1.241(5) 0.562(3) -0.037(2) 0.063(10) Uiso 1 1 d . . . . .
H4 H 1.506(4) 0.357(2) 0.017(2) 0.043(8) Uiso 1 1 d . . . . .
H8 H 0.727(6) 0.583(3) -0.137(3) 0.082(13) Uiso 1 1 d . . . . .
H5B H 1.316(5) 0.229(3) 0.017(2) 0.053(8) Uiso 1 1 d . . . . .
H9 H 0.727(4) 0.474(2) -0.022(2) 0.050(8) Uiso 1 1 d . . . . .
H1A H 1.377(6) 0.343(3) 0.176(3) 0.068(11) Uiso 1 1 d . . . . .
H1B H 1.477(5) 0.266(3) 0.143(2) 0.058(9) Uiso 1 1 d . . . . .
H3B H 1.434(5) 0.511(3) 0.069(2) 0.052(8) Uiso 1 1 d . . . . .
H1 H 1.066(4) 0.420(2) -0.0245(19) 0.042(7) Uiso 1 1 d . . . . .
H1C H 1.544(6) 0.365(3) 0.152(3) 0.066(12) Uiso 1 1 d . . . . .
H11 H 0.960(5) 0.688(3) 0.125(2) 0.058(9) Uiso 1 1 d . . . . .
H2 H 0.899(6) 0.394(3) -0.203(3) 0.063(11) Uiso 1 1 d . . . . .
H13A H 0.790(7) 0.737(4) -0.201(4) 0.108(17) Uiso 1 1 d . . . . .
H13B H 0.765(8) 0.821(5) -0.149(4) 0.12(2) Uiso 1 1 d . . . . .
H13C H 0.953(9) 0.783(5) -0.165(4) 0.12(2) Uiso 1 1 d . . . . .
H12 H 0.964(6) 0.793(3) 0.004(3) 0.084(14) Uiso 1 1 d . . . . .
H2WB H 0.880(8) 0.902(4) 0.265(4) 0.112(18) 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 1.511(3) . ?
C1 C6 1.505(3) . ?
C1 O1 1.441(3) . ?
C1 H1 0.99(3) . ?
C2 C3 1.518(4) . ?
C2 H2A 1.03(3) . ?
C2 H2B 0.98(4) . ?
C3 C4 1.521(3) . ?
C3 H3A 0.95(3) . ?
C3 H3B 0.89(4) . ?
C4 C5 1.518(4) . ?
C4 N1 1.491(3) . ?
C4 H4 0.89(3) . ?
C5 O1 1.425(3) . ?
C5 H5A 1.00(3) . ?
C5 H5B 0.92(4) . ?
C6 O2 1.415(3) . ?
C6 H6A 0.99(3) . ?
C6 H6B 0.94(3) . ?
C7 C8 1.387(5) . ?
C7 C12 1.380(5) . ?
C7 C13 1.509(5) . ?
C8 C9 1.382(4) . ?
C8 H8 1.00(5) . ?
C9 C10 1.383(4) . ?
C9 H9 1.03(3) . ?
C10 C11 1.386(4) . ?
C10 S1 1.774(3) . ?
C11 C12 1.382(5) . ?
C11 H11 0.93(4) . ?
C12 H12 0.94(4) . ?
C13 H13A 1.00(6) . ?
C13 H13B 1.08(6) . ?
C13 H13C 0.77(7) . ?
N1 H1A 0.92(5) . ?
N1 H1B 0.91(4) . ?
N1 H1C 0.77(5) . ?
O2 H2 0.75(4) . ?
O3 S1 1.452(2) . ?
O4 S1 1.448(2) . ?
O5 S1 1.443(2) . ?
O2W H2WA 0.8502 . ?
O2W H2WB 0.90(6) . ?
O1W H1WA 0.8498 . ?
O1W H1WB 0.9841 . ?

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 H1 110.0(17) . . ?
C6 C1 C2 113.5(2) . . ?
C6 C1 H1 110.2(18) . . ?
O1 C1 C2 110.5(2) . . ?
O1 C1 C6 106.36(18) . . ?
O1 C1 H1 105.9(17) . . ?
C1 C2 C3 110.0(2) . . ?
C1 C2 H2A 107.4(18) . . ?
C1 C2 H2B 110(2) . . ?
C3 C2 H2A 112.4(17) . . ?
C3 C2 H2B 109(2) . . ?
H2A C2 H2B 108(3) . . ?
C2 C3 C4 109.7(2) . . ?
C2 C3 H3A 110.9(17) . . ?
C2 C3 H3B 112(2) . . ?
C4 C3 H3A 110.0(18) . . ?
C4 C3 H3B 113(2) . . ?
H3A C3 H3B 101(3) . . ?
C3 C4 H4 109(2) . . ?
C5 C4 C3 111.0(2) . . ?
C5 C4 H4 108(2) . . ?
N1 C4 C3 110.6(2) . . ?
N1 C4 C5 109.4(2) . . ?
N1 C4 H4 109(2) . . ?
C4 C5 H5A 110.1(16) . . ?
C4 C5 H5B 113(2) . . ?
O1 C5 C4 109.9(2) . . ?
O1 C5 H5A 108.8(16) . . ?
O1 C5 H5B 109(2) . . ?
H5A C5 H5B 107(3) . . ?
C1 C6 H6A 109.8(19) . . ?
C1 C6 H6B 106.2(18) . . ?
O2 C6 C1 108.4(2) . . ?
O2 C6 H6A 112.3(19) . . ?
O2 C6 H6B 113.7(19) . . ?
H6A C6 H6B 106(3) . . ?
C8 C7 C13 121.2(3) . . ?
C12 C7 C8 118.2(3) . . ?
C12 C7 C13 120.6(4) . . ?
C7 C8 H8 121(2) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 118(3) . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 116.2(18) . . ?
C10 C9 H9 124.2(18) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 S1 119.4(2) . . ?
C11 C10 S1 120.5(2) . . ?
C10 C11 H11 119(2) . . ?
C12 C11 C10 119.3(3) . . ?
C12 C11 H11 122(2) . . ?
C7 C12 C11 121.7(3) . . ?
C7 C12 H12 117(3) . . ?
C11 C12 H12 121(3) . . ?
C7 C13 H13A 108(3) . . ?
C7 C13 H13B 108(3) . . ?
C7 C13 H13C 113(6) . . ?
H13A C13 H13B 86(4) . . ?
H13A C13 H13C 120(6) . . ?
H13B C13 H13C 118(6) . . ?
C4 N1 H1A 107(3) . . ?
C4 N1 H1B 109(2) . . ?
C4 N1 H1C 106(3) . . ?
H1A N1 H1B 101(3) . . ?
H1A N1 H1C 113(4) . . ?
H1B N1 H1C 120(4) . . ?
C5 O1 C1 111.90(17) . . ?
C6 O2 H2 111(3) . . ?
O3 S1 C10 106.46(13) . . ?
O4 S1 C10 106.23(13) . . ?
O4 S1 O3 112.48(13) . . ?
O5 S1 C10 106.59(11) . . ?
O5 S1 O3 113.81(15) . . ?
O5 S1 O4 110.69(17) . . ?
H2WA O2W H2WB 97.9 . . ?
H1WA O1W H1WB 108.9 . . ?

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
O2W H2WA O1W 0.85 1.91 2.761(4) 176.2 . yes
O1W H1WB O3 0.98 1.86 2.837(3) 169.8 . yes
N1 H1A O2W 0.92(5) 1.87(5) 2.781(4) 176(4) 3_745 yes
N1 H1B O2 0.91(4) 1.94(4) 2.834(3) 167(3) 4 yes
O2 H2 O4 0.75(4) 2.04(4) 2.755(3) 157(4) 2_664 yes
O2W H2WB O3 0.90(6) 1.98(6) 2.880(3) 172(5) 3_755 yes

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 C2 C3 C4 53.3(3) . . . . ?
C2 C1 C6 O2 -171.7(2) . . . . ?
C2 C1 O1 C5 62.1(3) . . . . ?
C2 C3 C4 C5 -53.3(3) . . . . ?
C2 C3 C4 N1 -175.0(2) . . . . ?
C3 C4 C5 O1 56.6(3) . . . . ?
C4 C5 O1 C1 -61.0(3) . . . . ?
C6 C1 C2 C3 -176.9(2) . . . . ?
C6 C1 O1 C5 -174.3(2) . . . . ?
C7 C8 C9 C10 1.3(5) . . . . ?
C8 C7 C12 C11 0.3(6) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C8 C9 C10 S1 178.9(2) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
C9 C10 S1 O3 150.4(2) . . . . ?
C9 C10 S1 O4 -89.5(2) . . . . ?
C9 C10 S1 O5 28.6(3) . . . . ?
C10 C11 C12 C7 1.2(6) . . . . ?
C11 C10 S1 O3 -30.9(3) . . . . ?
C11 C10 S1 O4 89.1(3) . . . . ?
C11 C10 S1 O5 -152.8(3) . . . . ?
C12 C7 C8 C9 -1.5(5) . . . . ?
C13 C7 C8 C9 178.0(4) . . . . ?
C13 C7 C12 C11 -179.2(4) . . . . ?
N1 C4 C5 O1 179.1(2) . . . . ?
O1 C1 C2 C3 -57.4(3) . . . . ?
O1 C1 C6 O2 66.5(3) . . . . ?
S1 C10 C11 C12 179.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mdp019_0m
_database_code_depnum_ccdc_archive 'CCDC 2215969'
loop_
_audit_author_name
_audit_author_address
'Justin Newman'
;Merck and Co, Inc
United States of America
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2022-12-07 downloaded from the CCDC.
;
_audit_creation_date             2022-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 O3 S, C6 H12 N O2'
_chemical_formula_sum            'C13 H19 N O5 S'
_chemical_formula_weight         301.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.1009(3)
_cell_length_b                   12.5179(6)
_cell_length_c                   19.3009(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1474.02(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3732
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.588
_cell_measurement_theta_min      4.210
_shelx_estimated_absorpt_T_max   0.832
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0921 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.8972. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9588
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.616
_diffrn_reflns_theta_max         66.616
_diffrn_reflns_theta_min         4.209
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed-tube microsource X-ray generator'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2361
_reflns_number_total             2602
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 878 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.064(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2602
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.4108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4A) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4)
\\sim Ueq, Uanis(O5A) \\sim Ueq: with sigma of 0.05 and sigma for terminal
atoms of 0.1
3. Others
 Sof(O3A)=Sof(O4A)=Sof(O5A)=1-FVAR(1)
 Sof(O3)=Sof(O5)=Sof(O4)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C12(H12), C9(H9)
4.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.41957(19) 0.59033(7) 0.40828(6) 0.0661(3) Uani 1 1 d . . . . .
O2 O 0.2883(5) 0.8783(3) 0.34833(18) 0.0768(9) Uani 1 1 d . . . . .
O1 O 0.0807(7) 1.0228(3) 0.32497(19) 0.0905(10) Uani 1 1 d . . . . .
N1 N -0.0712(7) 0.7703(2) 0.40979(19) 0.0711(9) Uani 1 1 d . . . . .
H1A H 0.046818 0.733198 0.397389 0.085 Uiso 1 1 calc GR . . . .
H1B H -0.189243 0.728744 0.407087 0.085 Uiso 1 1 calc GR . . . .
H1C H -0.055249 0.793375 0.453121 0.085 Uiso 1 1 calc GR . . . .
C7 C 0.4815(5) 0.4525(3) 0.41121(19) 0.0473(8) Uani 1 1 d . . . . .
C11 C 0.7281(6) 0.3099(3) 0.4333(2) 0.0608(10) Uani 1 1 d . . . . .
H11 H 0.864676 0.286625 0.448463 0.073 Uiso 1 1 calc R . . . .
C8 C 0.3257(6) 0.3797(3) 0.3908(2) 0.0563(9) Uani 1 1 d . . . . .
H8 H 0.187658 0.402987 0.377052 0.068 Uiso 1 1 calc R . . . .
C12 C 0.6843(6) 0.4178(3) 0.4328(2) 0.0573(9) Uani 1 1 d . . . . .
H12 H 0.790404 0.466640 0.446767 0.069 Uiso 1 1 calc R . . . .
C10 C 0.5756(7) 0.2352(3) 0.4121(2) 0.0571(8) Uani 1 1 d . . . . .
C9 C 0.3742(6) 0.2723(3) 0.3906(2) 0.0586(9) Uani 1 1 d . . . . .
H9 H 0.268824 0.223756 0.375762 0.070 Uiso 1 1 calc R . . . .
C1 C -0.0979(7) 0.8630(3) 0.3628(2) 0.0610(10) Uani 1 1 d . . . . .
H1 H -0.228060 0.903359 0.377003 0.073 Uiso 1 1 calc R . . . .
O3 O 0.583(2) 0.6401(13) 0.4471(11) 0.101(7) Uani 0.369(13) 1 d . U P A 1
C2 C 0.1029(8) 0.9347(3) 0.3702(2) 0.0703(11) Uani 1 1 d . . . . .
H2 H 0.120013 0.958812 0.418226 0.084 Uiso 1 1 calc R . . . .
C6 C -0.1269(7) 0.8276(4) 0.2880(2) 0.0729(12) Uani 1 1 d . . . . .
H6A H -0.223097 0.765944 0.286429 0.088 Uiso 1 1 calc R . . . .
H6B H -0.195288 0.884623 0.261712 0.088 Uiso 1 1 calc R . . . .
C4 C 0.2618(8) 0.8790(5) 0.2741(3) 0.0839(15) Uani 1 1 d . . . . .
H4 H 0.400492 0.862793 0.250742 0.101 Uiso 1 1 calc R . . . .
C13 C 0.6288(9) 0.1180(3) 0.4120(3) 0.0859(14) Uani 1 1 d . . . . .
H13A H 0.710429 0.100761 0.370930 0.129 Uiso 1 1 calc GR . . . .
H13B H 0.495332 0.077445 0.412712 0.129 Uiso 1 1 calc GR . . . .
H13C H 0.714703 0.101041 0.452141 0.129 Uiso 1 1 calc GR . . . .
C5 C 0.0899(8) 0.7994(4) 0.2554(2) 0.0818(13) Uani 1 1 d . . . . .
H5A H 0.135014 0.729089 0.271006 0.098 Uiso 1 1 calc R . . . .
H5B H 0.073667 0.797026 0.205457 0.098 Uiso 1 1 calc R . . . .
O5 O 0.247(3) 0.5967(11) 0.4708(9) 0.123(6) Uani 0.369(13) 1 d . . P A 1
C3 C 0.1960(10) 0.9938(5) 0.2623(3) 0.1011(18) Uani 1 1 d . . . . .
H3A H 0.323918 1.038651 0.255654 0.121 Uiso 1 1 calc R . . . .
H3B H 0.101301 1.000232 0.222188 0.121 Uiso 1 1 calc R . . . .
O4 O 0.326(4) 0.6131(10) 0.3516(6) 0.146(11) Uani 0.369(13) 1 d . U P A 1
O3A O 0.518(3) 0.6381(10) 0.4648(6) 0.174(8) Uani 0.631(13) 1 d . U P A 2
O4A O 0.5408(18) 0.6328(5) 0.3479(5) 0.128(4) Uani 0.631(13) 1 d . U P A 2
O5A O 0.1996(9) 0.6023(5) 0.4057(9) 0.148(7) Uani 0.631(13) 1 d . U P A 2


_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 C7 1.768(3) . ?
S1 O3 1.396(15) . ?
S1 O5 1.603(17) . ?
S1 O4 1.267(8) . ?
S1 O3A 1.382(10) . ?
S1 O4A 1.480(6) . ?
S1 O5A 1.351(6) . ?
O2 C2 1.399(6) . ?
O2 C4 1.443(6) . ?
O1 C2 1.413(5) . ?
O1 C3 1.445(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.482(5) . ?
C7 C8 1.374(5) . ?
C7 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(6) . ?
C11 C10 1.382(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(5) . ?
C12 H12 0.9300 . ?
C10 C9 1.376(5) . ?
C10 C13 1.502(5) . ?
C9 H9 0.9300 . ?
C1 H1 0.9800 . ?
C1 C2 1.526(6) . ?
C1 C6 1.521(6) . ?
C2 H2 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.506(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.491(7) . ?
C4 C3 1.509(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 C7 105.4(8) . . ?
O3 S1 O5 92.5(9) . . ?
O5 S1 C7 99.5(5) . . ?
O4 S1 C7 110.1(6) . . ?
O4 S1 O3 133.4(12) . . ?
O4 S1 O5 109.9(11) . . ?
O3A S1 C7 107.7(5) . . ?
O3A S1 O4A 104.4(8) . . ?
O4A S1 C7 105.6(3) . . ?
O5A S1 C7 108.7(3) . . ?
O5A S1 O3A 114.4(9) . . ?
O5A S1 O4A 115.3(7) . . ?
C2 O2 C4 101.9(3) . . ?
C2 O1 C3 105.9(4) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C8 C7 S1 119.3(3) . . ?
C8 C7 C12 120.0(3) . . ?
C12 C7 S1 120.6(3) . . ?
C12 C11 H11 119.0 . . ?
C12 C11 C10 122.1(4) . . ?
C10 C11 H11 119.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C12 C11 119.1(4) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C11 C10 C13 121.0(4) . . ?
C9 C10 C11 117.5(3) . . ?
C9 C10 C13 121.4(4) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
N1 C1 H1 108.7 . . ?
N1 C1 C2 108.4(4) . . ?
N1 C1 C6 111.4(3) . . ?
C2 C1 H1 108.7 . . ?
C6 C1 H1 108.7 . . ?
C6 C1 C2 110.7(4) . . ?
O2 C2 O1 106.6(4) . . ?
O2 C2 C1 108.9(3) . . ?
O2 C2 H2 110.8 . . ?
O1 C2 C1 108.9(4) . . ?
O1 C2 H2 110.8 . . ?
C1 C2 H2 110.8 . . ?
C1 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C5 C6 C1 111.2(4) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
O2 C4 H4 111.0 . . ?
O2 C4 C5 108.3(4) . . ?
O2 C4 C3 100.7(4) . . ?
C5 C4 H4 111.0 . . ?
C5 C4 C3 114.4(5) . . ?
C3 C4 H4 111.0 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 C6 111.1(4) . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O1 C3 C4 104.1(4) . . ?
O1 C3 H3A 110.9 . . ?
O1 C3 H3B 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 109.0 . . ?

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 H1A O5A 0.89 1.89 2.676(6) 145.9 . yes
N1 H1B O3 0.89 1.94 2.761(12) 153.0 1_455 yes
N1 H1C O3A 0.89 1.86 2.733(13) 167.9 4_466 yes

_olex2_submission_special_instructions 'No special instructions were received'
