# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_TMP
_database_code_depnum_ccdc_archive 'CCDC 1916407'
_audit_update_record             
;
2019-05-16 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.05

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   16.1754(12)
_cell_length_b                   6.0607(4)
_cell_length_c                   12.2782(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1203.68(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      30.72

_exptl_crystal_description       rhombic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            17449
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         32.095
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3539
_reflns_number_gt                3188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_max     0.759
_reflns_Friedel_fraction_full    0.999

_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0464P)²+0.1652P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1154 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3539
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003

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 0.72295(3) 0.65185(8) 0.70301(4) 0.04283(14) Uani 1 1 d . . . . .
O1 O 0.63484(9) 0.3286(2) 0.38323(11) 0.0473(3) Uani 1 1 d . . . . .
H1 H 0.661774 0.441874 0.391985 0.071 Uiso 1 1 calc R U . . .
N1 N 0.71240(9) 0.6396(2) 0.49278(12) 0.0376(3) Uani 1 1 d . . . . .
C1 C 0.49209(15) -0.2109(4) 0.3723(2) 0.0605(6) Uani 1 1 d . . . . .
H5 H 0.519577 -0.333311 0.406228 0.091 Uiso 1 1 calc R U . . .
H6 H 0.481723 -0.244660 0.297140 0.091 Uiso 1 1 calc R U . . .
H11 H 0.440594 -0.183494 0.408740 0.091 Uiso 1 1 calc R U . . .
C2 C 0.56073(10) 0.0595(3) 0.48074(16) 0.0390(4) Uani 1 1 d . . . . .
C3 C 0.61070(9) 0.2499(3) 0.48094(15) 0.0354(3) Uani 1 1 d . . . . .
C4 C 0.63323(10) 0.3468(3) 0.58038(14) 0.0343(3) Uani 1 1 d . . . . .
C5 C 0.68676(10) 0.5404(3) 0.58095(14) 0.0337(3) Uani 1 1 d . . . . .
C6 C 0.76272(10) 0.8182(3) 0.51760(15) 0.0373(4) Uani 1 1 d . . . . .
C7 C 0.80031(13) 0.9581(4) 0.44256(18) 0.0499(5) Uani 1 1 d . . . . .
H10 H 0.792642 0.937480 0.368181 0.060 Uiso 1 1 calc R U . . .
C8 C 0.84922(13) 1.1282(4) 0.4808(2) 0.0553(5) Uani 1 1 d . . . . .
H2 H 0.874600 1.223022 0.431492 0.066 Uiso 1 1 calc R U . . .
C9 C 0.86104(12) 1.1596(4) 0.5919(2) 0.0522(5) Uani 1 1 d . . . . .
H3 H 0.894233 1.275442 0.615407 0.063 Uiso 1 1 calc R U . . .
C10 C 0.77538(10) 0.8518(3) 0.62921(15) 0.0375(3) Uani 1 1 d . . . . .
C11 C 0.60493(12) 0.2534(3) 0.67769(16) 0.0436(4) Uani 1 1 d . . . . .
H8 H 0.619396 0.317707 0.743764 0.052 Uiso 1 1 calc R U . . .
C12 C 0.55601(13) 0.0677(4) 0.67698(18) 0.0495(5) Uani 1 1 d . . . . .
H7 H 0.537547 0.007323 0.742234 0.059 Uiso 1 1 calc R U . . .
C13 C 0.53411(12) -0.0301(3) 0.57801(19) 0.0462(4) Uani 1 1 d . . . . .
H4 H 0.501403 -0.156295 0.577659 0.055 Uiso 1 1 calc R U . . .
C14 C 0.82491(12) 1.0238(3) 0.66768(19) 0.0464(4) Uani 1 1 d . . . . .
H9 H 0.833112 1.045494 0.741883 0.056 Uiso 1 1 calc R U . . .
O2 O 0.54317(9) -0.0196(3) 0.37942(13) 0.0530(4) 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 C10 1.7347(18) . ?
S1 C5 1.7449(18) . ?
O1 C3 1.349(2) . ?
O1 H1 0.8200 . ?
N1 C5 1.306(2) . ?
N1 C6 1.388(2) . ?
C1 O2 1.427(2) . ?
C1 H5 0.9600 . ?
C1 H6 0.9600 . ?
C1 H11 0.9600 . ?
C2 O2 1.363(2) . ?
C2 C13 1.381(3) . ?
C2 C3 1.409(2) . ?
C3 C4 1.403(2) . ?
C4 C11 1.399(3) . ?
C4 C5 1.458(2) . ?
C6 C7 1.392(3) . ?
C6 C10 1.400(3) . ?
C7 C8 1.382(3) . ?
C7 H10 0.9300 . ?
C8 C9 1.390(4) . ?
C8 H2 0.9300 . ?
C9 C14 1.373(3) . ?
C9 H3 0.9300 . ?
C10 C14 1.397(3) . ?
C11 C12 1.376(3) . ?
C11 H8 0.9300 . ?
C12 C13 1.398(3) . ?
C12 H7 0.9300 . ?
C13 H4 0.9300 . ?
C14 H9 0.9300 . ?

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
C10 S1 C5 89.18(8) . . ?
C3 O1 H1 109.5 . . ?
C5 N1 C6 111.29(14) . . ?
O2 C1 H5 109.5 . . ?
O2 C1 H6 109.5 . . ?
H5 C1 H6 109.5 . . ?
O2 C1 H11 109.5 . . ?
H5 C1 H11 109.5 . . ?
H6 C1 H11 109.5 . . ?
O2 C2 C13 125.90(17) . . ?
O2 C2 C3 114.14(17) . . ?
C13 C2 C3 119.96(18) . . ?
O1 C3 C4 123.41(15) . . ?
O1 C3 C2 117.02(16) . . ?
C4 C3 C2 119.57(16) . . ?
C11 C4 C3 119.25(16) . . ?
C11 C4 C5 121.05(16) . . ?
C3 C4 C5 119.69(15) . . ?
N1 C5 C4 123.71(15) . . ?
N1 C5 S1 115.30(13) . . ?
C4 C5 S1 120.98(13) . . ?
C7 C6 N1 125.86(18) . . ?
C7 C6 C10 119.67(17) . . ?
N1 C6 C10 114.46(15) . . ?
C8 C7 C6 118.7(2) . . ?
C8 C7 H10 120.7 . . ?
C6 C7 H10 120.7 . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H2 119.5 . . ?
C9 C8 H2 119.5 . . ?
C14 C9 C8 121.6(2) . . ?
C14 C9 H3 119.2 . . ?
C8 C9 H3 119.2 . . ?
C14 C10 C6 121.57(18) . . ?
C14 C10 S1 128.68(16) . . ?
C6 C10 S1 109.75(13) . . ?
C12 C11 C4 120.92(19) . . ?
C12 C11 H8 119.5 . . ?
C4 C11 H8 119.5 . . ?
C11 C12 C13 119.87(19) . . ?
C11 C12 H7 120.1 . . ?
C13 C12 H7 120.1 . . ?
C2 C13 C12 120.42(17) . . ?
C2 C13 H4 119.8 . . ?
C12 C13 H4 119.8 . . ?
C9 C14 C10 117.5(2) . . ?
C9 C14 H9 121.2 . . ?
C10 C14 H9 121.2 . . ?
C2 O2 C1 117.53(18) . . ?

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
O2 C2 C3 O1 -0.2(2) . . . . ?
C13 C2 C3 O1 179.79(17) . . . . ?
O2 C2 C3 C4 -179.87(16) . . . . ?
C13 C2 C3 C4 0.2(3) . . . . ?
O1 C3 C4 C11 179.83(16) . . . . ?
C2 C3 C4 C11 -0.6(2) . . . . ?
O1 C3 C4 C5 -1.2(2) . . . . ?
C2 C3 C4 C5 178.37(15) . . . . ?
C6 N1 C5 C4 -179.73(14) . . . . ?
C6 N1 C5 S1 -1.13(18) . . . . ?
C11 C4 C5 N1 -177.25(16) . . . . ?
C3 C4 C5 N1 3.8(2) . . . . ?
C11 C4 C5 S1 4.2(2) . . . . ?
C3 C4 C5 S1 -174.70(12) . . . . ?
C10 S1 C5 N1 1.17(14) . . . . ?
C10 S1 C5 C4 179.81(13) . . . . ?
C5 N1 C6 C7 179.82(17) . . . . ?
C5 N1 C6 C10 0.4(2) . . . . ?
N1 C6 C7 C8 -179.57(18) . . . . ?
C10 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C14 0.0(4) . . . . ?
C7 C6 C10 C14 0.2(3) . . . . ?
N1 C6 C10 C14 179.60(15) . . . . ?
C7 C6 C10 S1 -179.00(14) . . . . ?
N1 C6 C10 S1 0.41(18) . . . . ?
C5 S1 C10 C14 -179.94(17) . . . . ?
C5 S1 C10 C6 -0.83(13) . . . . ?
C3 C4 C11 C12 0.4(3) . . . . ?
C5 C4 C11 C12 -178.48(17) . . . . ?
C4 C11 C12 C13 0.1(3) . . . . ?
O2 C2 C13 C12 -179.59(18) . . . . ?
C3 C2 C13 C12 0.4(3) . . . . ?
C11 C12 C13 C2 -0.5(3) . . . . ?
C8 C9 C14 C10 -0.1(3) . . . . ?
C6 C10 C14 C9 0.0(3) . . . . ?
S1 C10 C14 C9 179.00(15) . . . . ?
C13 C2 O2 C1 0.6(3) . . . . ?
C3 C2 O2 C1 -179.35(16) . . . . ?

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
C14 H9 O2 0.93 2.62 3.363(3) 137.0 4_665
O1 H1 N1 0.82 1.91 2.6334(19) 147.0 .
C14 H9 O2 0.93 2.62 3.363(3) 137.0 4_665
O1 H1 N1 0.82 1.91 2.6334(19) 147.0 .
C1 H6 O2 0.96 2.76 3.657(3) 155.2 3_645
C14 H9 O2 0.93 2.62 3.363(3) 137.0 4_665
O1 H1 N1 0.82 1.91 2.6334(19) 147.0 .
C14 H9 O2 0.93 2.62 3.363(3) 137.0 4_665

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040

