# 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. 
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data_MDH_thiochrom
_database_code_depnum_ccdc_archive 'CCDC 1506303'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;
_audit_creation_date             2016-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 N O2 S'
_chemical_formula_sum            'C15 H11 N O2 S'
_chemical_formula_weight         269.31
_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 0.0033 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.9636(3)
_cell_length_b                   10.3969(4)
_cell_length_c                   13.4271(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.8620(10)
_cell_angle_gamma                90
_cell_volume                     1246.82(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9096
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.257
_cell_measurement_theta_min      3.007
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0541 before and 0.0452 after correction. The Ratio of minimum to maximum transmission is 0.9662. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31745
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         3.007
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2788
_reflns_number_total             3105
_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       'APEX2 (Bruker, 2013)'
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.7448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0747
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.60566(10) 0.41529(9) 0.21824(7) 0.02086(19) Uani 1 1 d . . . . .
N1 N 0.51401(11) 0.50186(10) 0.22672(7) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.30636(12) 0.60645(11) 0.30994(8) 0.0124(2) Uani 1 1 d . . . . .
H1 H 0.3566 0.6862 0.2879 0.015 Uiso 1 1 calc R . . . .
C2 C 0.41995(12) 0.50004(11) 0.31140(8) 0.0123(2) Uani 1 1 d . . . . .
O2 O 0.49419(11) 0.59096(9) 0.16658(7) 0.0264(2) Uani 1 1 d . . . . .
C3 C 0.43775(12) 0.40168(11) 0.37554(8) 0.0129(2) Uani 1 1 d . . . . .
H3 H 0.5112 0.3386 0.3643 0.015 Uiso 1 1 calc R . . . .
C4 C 0.35118(12) 0.38582(11) 0.46138(8) 0.0125(2) Uani 1 1 d . . . . .
C5 C 0.36398(13) 0.27127(11) 0.51678(9) 0.0152(2) Uani 1 1 d . . . . .
H5 H 0.4272 0.2044 0.4968 0.018 Uiso 1 1 calc R . . . .
C6 C 0.28515(13) 0.25476(12) 0.60042(9) 0.0178(2) Uani 1 1 d . . . . .
H6 H 0.2955 0.1773 0.6379 0.021 Uiso 1 1 calc R . . . .
C7 C 0.19087(13) 0.35182(12) 0.62937(9) 0.0175(2) Uani 1 1 d . . . . .
H7 H 0.1367 0.3402 0.6865 0.021 Uiso 1 1 calc R . . . .
C8 C 0.17560(13) 0.46564(12) 0.57505(9) 0.0156(2) Uani 1 1 d . . . . .
H8 H 0.1098 0.5309 0.5945 0.019 Uiso 1 1 calc R . . . .
C9 C 0.25701(12) 0.48422(11) 0.49183(8) 0.0129(2) Uani 1 1 d . . . . .
S10 S 0.25113(3) 0.63725(3) 0.43625(2) 0.01395(8) Uani 1 1 d . . . . .
C11 C 0.17086(12) 0.58347(11) 0.23601(8) 0.0124(2) Uani 1 1 d . . . . .
C12 C 0.08853(13) 0.46960(11) 0.23702(8) 0.0143(2) Uani 1 1 d . . . . .
H12 H 0.1194 0.4030 0.2827 0.017 Uiso 1 1 calc R . . . .
C13 C -0.03873(13) 0.45333(12) 0.17124(9) 0.0175(2) Uani 1 1 d . . . . .
H13 H -0.0944 0.3757 0.1722 0.021 Uiso 1 1 calc R . . . .
C14 C -0.08468(14) 0.55046(13) 0.10415(9) 0.0197(2) Uani 1 1 d . . . . .
H14 H -0.1723 0.5395 0.0600 0.024 Uiso 1 1 calc R . . . .
C15 C -0.00233(14) 0.66319(12) 0.10197(9) 0.0200(3) Uani 1 1 d . . . . .
H15 H -0.0330 0.7293 0.0559 0.024 Uiso 1 1 calc R . . . .
C16 C 0.12555(13) 0.67939(12) 0.16749(9) 0.0169(2) Uani 1 1 d . . . . .
H16 H 0.1822 0.7564 0.1654 0.020 Uiso 1 1 calc R . . . .


_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 N1 1.2304(13) . ?
N1 C2 1.4719(14) . ?
N1 O2 1.2318(13) . ?
C1 H1 1.0000 . ?
C1 C2 1.5025(15) . ?
C1 S10 1.8348(11) . ?
C1 C11 1.5210(15) . ?
C2 C3 1.3377(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.4525(15) . ?
C4 C5 1.4037(16) . ?
C4 C9 1.4089(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3872(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3926(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3907(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3988(16) . ?
C9 S10 1.7562(12) . ?
C11 C12 1.3958(16) . ?
C11 C16 1.3938(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3925(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3921(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3868(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3947(17) . ?
C16 H16 0.9500 . ?

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 N1 C2 119.52(9) . . ?
O1 N1 O2 123.36(10) . . ?
O2 N1 C2 117.12(9) . . ?
C2 C1 H1 107.0 . . ?
C2 C1 S10 110.62(8) . . ?
C2 C1 C11 113.30(9) . . ?
S10 C1 H1 107.0 . . ?
C11 C1 H1 107.0 . . ?
C11 C1 S10 111.57(7) . . ?
N1 C2 C1 114.35(9) . . ?
C3 C2 N1 117.53(10) . . ?
C3 C2 C1 127.95(10) . . ?
C2 C3 H3 118.1 . . ?
C2 C3 C4 123.72(10) . . ?
C4 C3 H3 118.1 . . ?
C5 C4 C3 119.45(10) . . ?
C5 C4 C9 119.11(10) . . ?
C9 C4 C3 121.42(10) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.63(11) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.94(11) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.35(11) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.11(11) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 S10 122.12(9) . . ?
C8 C9 C4 119.83(10) . . ?
C8 C9 S10 117.76(9) . . ?
C9 S10 C1 103.53(5) . . ?
C12 C11 C1 121.37(10) . . ?
C16 C11 C1 119.36(10) . . ?
C16 C11 C12 119.25(10) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.15(11) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.26(11) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.86(11) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.95(11) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.52(11) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?

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
O1 N1 C2 C1 -176.50(10) . . . . ?
O1 N1 C2 C3 -0.80(15) . . . . ?
N1 C2 C3 C4 -178.86(10) . . . . ?
C1 C2 C3 C4 -3.83(18) . . . . ?
C1 C11 C12 C13 177.29(10) . . . . ?
C1 C11 C16 C15 -177.03(10) . . . . ?
C2 C1 S10 C9 -34.40(9) . . . . ?
C2 C1 C11 C12 52.96(14) . . . . ?
C2 C1 C11 C16 -128.72(11) . . . . ?
C2 C3 C4 C5 171.70(11) . . . . ?
C2 C3 C4 C9 -9.81(17) . . . . ?
O2 N1 C2 C1 2.46(14) . . . . ?
O2 N1 C2 C3 178.16(11) . . . . ?
C3 C4 C5 C6 178.54(10) . . . . ?
C3 C4 C9 C8 -179.83(10) . . . . ?
C3 C4 C9 S10 -6.19(15) . . . . ?
C4 C5 C6 C7 0.77(18) . . . . ?
C4 C9 S10 C1 26.86(10) . . . . ?
C5 C4 C9 C8 -1.33(16) . . . . ?
C5 C4 C9 S10 172.31(8) . . . . ?
C5 C6 C7 C8 -0.23(18) . . . . ?
C6 C7 C8 C9 -1.10(17) . . . . ?
C7 C8 C9 C4 1.88(17) . . . . ?
C7 C8 C9 S10 -172.03(9) . . . . ?
C8 C9 S10 C1 -159.38(9) . . . . ?
C9 C4 C5 C6 0.01(17) . . . . ?
S10 C1 C2 N1 -156.79(8) . . . . ?
S10 C1 C2 C3 28.04(15) . . . . ?
S10 C1 C11 C12 -72.66(12) . . . . ?
S10 C1 C11 C16 105.65(10) . . . . ?
C11 C1 C2 N1 77.07(12) . . . . ?
C11 C1 C2 C3 -98.09(13) . . . . ?
C11 C1 S10 C9 92.70(8) . . . . ?
C11 C12 C13 C14 -0.03(17) . . . . ?
C12 C11 C16 C15 1.33(17) . . . . ?
C12 C13 C14 C15 0.81(18) . . . . ?
C13 C14 C15 C16 -0.51(19) . . . . ?
C14 C15 C16 C11 -0.57(18) . . . . ?
C16 C11 C12 C13 -1.03(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
