# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_LOH-868
_database_code_depnum_ccdc_archive 'CCDC 1823711'
_audit_update_record             
;
2018-02-13 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N O5 S'
_chemical_formula_sum            'C19 H15 N O5 S'
_chemical_formula_weight         369.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.0651(2)
_cell_length_b                   7.1483(3)
_cell_length_c                   17.7906(5)
_cell_angle_alpha                83.865(3)
_cell_angle_beta                 81.293(2)
_cell_angle_gamma                75.066(3)
_cell_volume                     855.96(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7079
_cell_measurement_theta_min      4.2950
_cell_measurement_theta_max      29.9410

_exptl_crystal_description       'parallelepipedic stick'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.11929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo)mm003 X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Rigaku double bounce layer mirror'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'HPAD Dectris PILATUS3R  200K'
_diffrn_reflns_number            16370
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.629
_diffrn_reflns_theta_max         29.645
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4388
_reflns_number_gt                3571
_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_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)+(0.0632P)²+0.1153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4383
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 1.0377(2) 0.2214(2) 0.07707(8) 0.0387(3) Uani 1 1 d . . . . .
C2 C 0.8484(2) 0.24406(19) 0.06400(7) 0.0353(3) Uani 1 1 d . . . . .
C3 C 1.1011(2) 0.1906(2) 0.15090(9) 0.0455(3) Uani 1 1 d . . . . .
O4 O 0.94571(14) 0.18982(16) 0.20921(5) 0.0434(2) Uani 1 1 d . . . . .
C5 C 0.75292(19) 0.21765(19) 0.19649(7) 0.0353(3) Uani 1 1 d . . . . .
C6 C 0.69678(19) 0.2436(2) 0.12709(8) 0.0372(3) Uani 1 1 d . . . . .
H6 H 0.565475 0.260504 0.120061 0.045 Uiso 1 1 calc R U . . .
O7 O 1.26376(18) 0.1664(3) 0.16811(8) 0.0736(4) Uani 1 1 d . . . . .
N8 N 0.62487(19) 0.20599(18) 0.26415(7) 0.0436(3) Uani 1 1 d . . . . .
C9 C 0.5709(3) 0.0238(3) 0.29017(10) 0.0524(4) Uani 1 1 d . . . . .
H9A H 0.482904 0.040100 0.337027 0.079 Uiso 0.58(2) 1 calc R U P . .
H9B H 0.506571 -0.012664 0.252252 0.079 Uiso 0.58(2) 1 calc R U P . .
H9C H 0.687823 -0.075797 0.298365 0.079 Uiso 0.58(2) 1 calc R U P . .
H9D H 0.635295 -0.072341 0.254735 0.079 Uiso 0.42(2) 1 calc R U P . .
H9E H 0.611628 -0.019577 0.339510 0.079 Uiso 0.42(2) 1 calc R U P . .
H9F H 0.430376 0.043556 0.293397 0.079 Uiso 0.42(2) 1 calc R U P . .
S10 S 0.54638(5) 0.39054(5) 0.31743(2) 0.04028(13) Uani 1 1 d . . . . .
C11 C 0.8527(2) 0.2696(2) -0.01748(8) 0.0421(3) Uani 1 1 d . . . . .
C12 C 1.0494(3) 0.2617(2) -0.04626(9) 0.0468(4) Uani 1 1 d . . . . .
O13 O 1.16599(16) 0.23044(17) 0.01158(6) 0.0491(3) Uani 1 1 d . . . . .
C14 C 0.7120(3) 0.2992(3) -0.06799(10) 0.0596(4) Uani 1 1 d . . . . .
H14 H 0.579998 0.304380 -0.050370 0.072 Uiso 1 1 calc R U . . .
C15 C 0.7767(4) 0.3203(3) -0.14507(11) 0.0756(6) Uani 1 1 d . . . . .
H15 H 0.686678 0.339059 -0.179947 0.091 Uiso 1 1 calc R U . . .
C16 C 0.9742(4) 0.3141(3) -0.17146(10) 0.0737(6) Uani 1 1 d . . . . .
H16 H 1.011854 0.330756 -0.223649 0.088 Uiso 1 1 calc R U . . .
C17 C 1.1152(3) 0.2844(3) -0.12313(10) 0.0635(5) Uani 1 1 d . . . . .
H17 H 1.246883 0.279720 -0.141041 0.076 Uiso 1 1 calc R U . . .
O18 O 0.6072(2) 0.54997(16) 0.27416(6) 0.0545(3) Uani 1 1 d . . . . .
O19 O 0.34212(16) 0.4049(2) 0.34315(7) 0.0600(3) Uani 1 1 d . . . . .
C20 C 0.6727(2) 0.3287(2) 0.39820(8) 0.0374(3) Uani 1 1 d . . . . .
C21 C 0.8656(2) 0.3437(2) 0.39287(9) 0.0459(3) Uani 1 1 d . . . . .
H21 H 0.929775 0.383608 0.346719 0.055 Uiso 1 1 calc R U . . .
C22 C 0.9617(2) 0.2988(3) 0.45683(10) 0.0533(4) Uani 1 1 d . . . . .
H22 H 1.091243 0.309442 0.453219 0.064 Uiso 1 1 calc R U . . .
C23 C 0.8704(3) 0.2383(2) 0.52630(9) 0.0495(4) Uani 1 1 d . . . . .
C24 C 0.6778(3) 0.2238(3) 0.53028(10) 0.0592(4) Uani 1 1 d . . . . .
H24 H 0.614065 0.183252 0.576409 0.071 Uiso 1 1 calc R U . . .
C25 C 0.5778(2) 0.2685(3) 0.46684(9) 0.0541(4) Uani 1 1 d . . . . .
H25 H 0.448124 0.258043 0.470400 0.065 Uiso 1 1 calc R U . . .
C26 C 0.9770(3) 0.1907(3) 0.59575(12) 0.0693(6) Uani 1 1 d . . . . .
H26A H 1.108332 0.208706 0.582597 0.104 Uiso 0.49(3) 1 calc R U P . .
H26B H 0.906958 0.274901 0.634804 0.104 Uiso 0.49(3) 1 calc R U P . .
H26C H 0.983656 0.058202 0.614104 0.104 Uiso 0.49(3) 1 calc R U P . .
H26D H 0.890965 0.152500 0.638406 0.104 Uiso 0.51(3) 1 calc R U P . .
H26E H 1.092339 0.086305 0.586199 0.104 Uiso 0.51(3) 1 calc R U P . .
H26F H 1.015641 0.303004 0.606899 0.104 Uiso 0.51(3) 1 calc R U P . .


_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 1.3577(19) . ?
C1 O13 1.3702(16) . ?
C1 C3 1.428(2) . ?
C2 C6 1.4299(18) . ?
C2 C11 1.4382(19) . ?
C3 O7 1.1990(18) . ?
C3 O4 1.3922(17) . ?
O4 C5 1.3748(16) . ?
C5 C6 1.3332(19) . ?
C5 N8 1.4008(16) . ?
N8 C9 1.4589(19) . ?
N8 S10 1.6363(12) . ?
S10 O19 1.4270(11) . ?
S10 O18 1.4286(12) . ?
S10 C20 1.7625(14) . ?
C11 C12 1.396(2) . ?
C11 C14 1.401(2) . ?
C12 O13 1.378(2) . ?
C12 C17 1.383(2) . ?
C14 C15 1.383(3) . ?
C15 C16 1.394(3) . ?
C16 C17 1.374(3) . ?
C20 C21 1.383(2) . ?
C20 C25 1.384(2) . ?
C21 C22 1.379(2) . ?
C22 C23 1.385(2) . ?
C23 C24 1.381(2) . ?
C23 C26 1.507(2) . ?
C24 C25 1.387(2) . ?

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 O13 113.21(13) . . ?
C2 C1 C3 124.51(12) . . ?
O13 C1 C3 122.28(13) . . ?
C1 C2 C6 119.56(12) . . ?
C1 C2 C11 105.68(12) . . ?
C6 C2 C11 134.74(13) . . ?
O7 C3 O4 118.08(15) . . ?
O7 C3 C1 129.42(15) . . ?
O4 C3 C1 112.50(12) . . ?
C5 O4 C3 123.30(11) . . ?
C6 C5 O4 123.39(12) . . ?
C6 C5 N8 124.06(12) . . ?
O4 C5 N8 112.48(12) . . ?
C5 C6 C2 116.71(12) . . ?
C5 N8 C9 119.87(12) . . ?
C5 N8 S10 120.62(9) . . ?
C9 N8 S10 119.38(10) . . ?
O19 S10 O18 120.12(8) . . ?
O19 S10 N8 107.27(7) . . ?
O18 S10 N8 106.19(6) . . ?
O19 S10 C20 107.26(7) . . ?
O18 S10 C20 108.83(7) . . ?
N8 S10 C20 106.43(7) . . ?
C12 C11 C14 119.46(15) . . ?
C12 C11 C2 105.31(13) . . ?
C14 C11 C2 135.22(15) . . ?
O13 C12 C17 125.29(16) . . ?
O13 C12 C11 111.25(12) . . ?
C17 C12 C11 123.47(18) . . ?
C1 O13 C12 104.55(11) . . ?
C15 C14 C11 117.5(2) . . ?
C14 C15 C16 121.3(2) . . ?
C17 C16 C15 122.36(17) . . ?
C16 C17 C12 115.94(19) . . ?
C21 C20 C25 120.33(14) . . ?
C21 C20 S10 119.69(11) . . ?
C25 C20 S10 119.97(11) . . ?
C22 C21 C20 119.19(14) . . ?
C21 C22 C23 121.77(15) . . ?
C24 C23 C22 118.07(14) . . ?
C24 C23 C26 120.79(17) . . ?
C22 C23 C26 121.14(17) . . ?
C23 C24 C25 121.30(15) . . ?
C20 C25 C24 119.33(15) . . ?

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
O13 C1 C2 C6 -178.21(12) . . . . ?
C3 C1 C2 C6 1.9(2) . . . . ?
O13 C1 C2 C11 0.26(16) . . . . ?
C3 C1 C2 C11 -179.62(14) . . . . ?
C2 C1 C3 O7 178.85(17) . . . . ?
O13 C1 C3 O7 -1.0(3) . . . . ?
C2 C1 C3 O4 -1.2(2) . . . . ?
O13 C1 C3 O4 178.98(12) . . . . ?
O7 C3 O4 C5 179.41(14) . . . . ?
C1 C3 O4 C5 -0.6(2) . . . . ?
C3 O4 C5 C6 1.6(2) . . . . ?
C3 O4 C5 N8 178.62(12) . . . . ?
O4 C5 C6 C2 -0.8(2) . . . . ?
N8 C5 C6 C2 -177.48(12) . . . . ?
C1 C2 C6 C5 -0.9(2) . . . . ?
C11 C2 C6 C5 -178.79(15) . . . . ?
C6 C5 N8 C9 80.93(19) . . . . ?
O4 C5 N8 C9 -96.06(15) . . . . ?
C6 C5 N8 S10 -103.14(15) . . . . ?
O4 C5 N8 S10 79.87(14) . . . . ?
C5 N8 S10 O19 138.81(12) . . . . ?
C9 N8 S10 O19 -45.25(14) . . . . ?
C5 N8 S10 O18 9.21(14) . . . . ?
C9 N8 S10 O18 -174.84(12) . . . . ?
C5 N8 S10 C20 -106.63(12) . . . . ?
C9 N8 S10 C20 69.31(13) . . . . ?
C1 C2 C11 C12 -0.68(15) . . . . ?
C6 C2 C11 C12 177.44(15) . . . . ?
C1 C2 C11 C14 179.90(17) . . . . ?
C6 C2 C11 C14 -2.0(3) . . . . ?
C14 C11 C12 O13 -179.57(14) . . . . ?
C2 C11 C12 O13 0.90(16) . . . . ?
C14 C11 C12 C17 0.9(2) . . . . ?
C2 C11 C12 C17 -178.63(14) . . . . ?
C2 C1 O13 C12 0.28(16) . . . . ?
C3 C1 O13 C12 -179.84(13) . . . . ?
C17 C12 O13 C1 178.78(15) . . . . ?
C11 C12 O13 C1 -0.74(15) . . . . ?
C12 C11 C14 C15 -0.3(2) . . . . ?
C2 C11 C14 C15 179.05(17) . . . . ?
C11 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
O13 C12 C17 C16 179.97(15) . . . . ?
C11 C12 C17 C16 -0.6(2) . . . . ?
O19 S10 C20 C21 -166.81(12) . . . . ?
O18 S10 C20 C21 -35.43(14) . . . . ?
N8 S10 C20 C21 78.63(13) . . . . ?
O19 S10 C20 C25 12.14(16) . . . . ?
O18 S10 C20 C25 143.52(14) . . . . ?
N8 S10 C20 C25 -102.43(14) . . . . ?
C25 C20 C21 C22 -0.3(2) . . . . ?
S10 C20 C21 C22 178.65(12) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C21 C22 C23 C26 -179.69(15) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C26 C23 C24 C25 179.56(17) . . . . ?
C21 C20 C25 C24 0.2(3) . . . . ?
S10 C20 C25 C24 -178.78(14) . . . . ?
C23 C24 C25 C20 0.0(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
_geom_hbond_publ_flag
C6 H6 O7 0.93 2.41 3.2099(18) 144.6 1_455 yes
C9 H9B O7 0.96 2.46 3.206(2) 134.3 1_455 yes

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.045

