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

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

data_lcq137
_database_code_depnum_ccdc_archive 'CCDC 1919695'
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2019-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O4 S3'
_chemical_formula_weight         354.41

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                   11.5057(16)
_cell_length_b                   9.9709(14)
_cell_length_c                   13.652(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.100(4)
_cell_angle_gamma                90
_cell_volume                     1512.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      24.75

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.508
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_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            13844
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.561
_diffrn_reflns_theta_max         24.767
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             2588
_reflns_number_gt                2446
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0340P)²+0.9855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2588
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
S1 S 0.59302(3) 0.80202(4) 0.15705(3) 0.01669(11) Uani 1 1 d . . . . .
S2 S 0.63289(3) 0.70097(4) -0.03512(3) 0.02066(12) Uani 1 1 d . . . . .
S3 S 0.65725(3) 0.51407(4) 0.13202(3) 0.01834(11) Uani 1 1 d . . . . .
O2 O 0.66378(10) 0.78198(12) 0.25850(8) 0.0234(3) Uani 1 1 d . . . . .
O1 O 0.60928(11) 0.92001(11) 0.10312(9) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.61012(11) 0.51015(12) 0.21811(10) 0.0302(3) Uani 1 1 d . . . . .
O3 O 0.61256(11) 0.42646(12) 0.04850(10) 0.0325(3) Uani 1 1 d . . . . .
C7 C 0.40629(15) 0.70077(16) 0.22100(13) 0.0227(3) Uani 1 1 d . . . . .
H7 H 0.4639 0.6555 0.2704 0.027 Uiso 1 1 calc R U . . .
C4 C 0.23592(16) 0.83727(19) 0.07303(14) 0.0340(4) Uani 1 1 d . . . . .
H4 H 0.1781 0.8828 0.0239 0.041 Uiso 1 1 calc R U . . .
C8 C 0.81416(14) 0.50046(15) 0.16849(12) 0.0198(3) Uani 1 1 d . . . . .
C3 C 0.35661(15) 0.85006(17) 0.07526(12) 0.0256(4) Uani 1 1 d . . . . .
H3 H 0.3809 0.9034 0.0283 0.031 Uiso 1 1 calc R U . . .
N1 N 0.62997(11) 0.67375(13) 0.08626(9) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.28562(16) 0.68980(18) 0.21697(15) 0.0309(4) Uani 1 1 d . . . . .
H6 H 0.2612 0.6368 0.2640 0.037 Uiso 1 1 calc R U . . .
C1 C 0.77358(15) 0.76969(17) -0.01429(12) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.43999(14) 0.78068(15) 0.14991(11) 0.0183(3) Uani 1 1 d . . . . .
C9 C 0.87671(17) 0.5492(2) 0.26183(14) 0.0349(4) Uani 1 1 d . . . . .
H9 H 0.8376 0.5963 0.3026 0.042 Uiso 1 1 calc R U . . .
N2 N 0.86720(15) 0.81582(18) -0.00229(12) 0.0364(4) Uani 1 1 d . . . . .
C5 C 0.20072(16) 0.7577(2) 0.14295(16) 0.0356(4) Uani 1 1 d . . . . .
H5 H 0.1194 0.7495 0.1403 0.043 Uiso 1 1 calc R U . . .
C13 C 0.86988(18) 0.4331(2) 0.10513(17) 0.0399(5) Uani 1 1 d . . . . .
H13 H 0.8266 0.4034 0.0415 0.048 Uiso 1 1 calc R U . . .
C10 C 0.9989(2) 0.5261(2) 0.2930(2) 0.0577(7) Uani 1 1 d . . . . .
H10 H 1.0430 0.5584 0.3555 0.069 Uiso 1 1 calc R U . . .
C11 C 1.05547(18) 0.4566(2) 0.2334(3) 0.0645(8) Uani 1 1 d . . . . .
H11 H 1.1376 0.4396 0.2564 0.077 Uiso 1 1 calc R U . . .
C12 C 0.9929(2) 0.4111(2) 0.1397(3) 0.0640(8) Uani 1 1 d . . . . .
H12 H 1.0332 0.3653 0.0991 0.077 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 O1 1.4259(12) . ?
S1 O2 1.4261(12) . ?
S1 N1 1.7218(13) . ?
S1 C2 1.7508(16) . ?
S2 N1 1.6881(12) . ?
S2 C1 1.7120(18) . ?
S3 O4 1.4173(13) . ?
S3 O3 1.4220(12) . ?
S3 N1 1.7093(13) . ?
S3 C8 1.7485(16) . ?
C7 C6 1.379(2) . ?
C7 C2 1.387(2) . ?
C4 C5 1.381(3) . ?
C4 C3 1.387(3) . ?
C8 C9 1.378(2) . ?
C8 C13 1.378(3) . ?
C3 C2 1.389(2) . ?
C6 C5 1.385(3) . ?
C1 N2 1.143(2) . ?
C9 C10 1.378(3) . ?
C13 C12 1.388(3) . ?
C10 C11 1.357(4) . ?
C11 C12 1.371(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
O1 S1 O2 119.91(7) . . ?
O1 S1 N1 103.78(7) . . ?
O2 S1 N1 106.21(7) . . ?
O1 S1 C2 109.69(7) . . ?
O2 S1 C2 110.39(7) . . ?
N1 S1 C2 105.68(7) . . ?
N1 S2 C1 99.27(7) . . ?
O4 S3 O3 120.76(8) . . ?
O4 S3 N1 104.79(6) . . ?
O3 S3 N1 106.59(7) . . ?
O4 S3 C8 110.57(8) . . ?
O3 S3 C8 108.15(8) . . ?
N1 S3 C8 104.72(7) . . ?
C6 C7 C2 118.67(16) . . ?
C5 C4 C3 120.66(16) . . ?
C9 C8 C13 122.40(17) . . ?
C9 C8 S3 119.19(13) . . ?
C13 C8 S3 118.27(14) . . ?
C4 C3 C2 117.82(16) . . ?
S2 N1 S3 117.37(7) . . ?
S2 N1 S1 120.17(8) . . ?
S3 N1 S1 122.37(7) . . ?
C7 C6 C5 120.10(17) . . ?
N2 C1 S2 178.73(15) . . ?
C7 C2 C3 122.28(15) . . ?
C7 C2 S1 119.43(12) . . ?
C3 C2 S1 118.22(13) . . ?
C10 C9 C8 118.1(2) . . ?
C4 C5 C6 120.47(16) . . ?
C8 C13 C12 117.6(2) . . ?
C11 C10 C9 120.7(2) . . ?
C10 C11 C12 120.7(2) . . ?
C11 C12 C13 120.4(2) . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3



