# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_mo_vyf961a_0m
_database_code_depnum_ccdc_archive 'CCDC 1820486'
_audit_update_record             
;
2018-01-30 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O2 S'
_chemical_formula_sum            'C14 H15 N O2 S'
_chemical_formula_weight         261.33

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.4454(12)
_cell_length_b                   7.2057(10)
_cell_length_c                   10.9962(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.797(2)
_cell_angle_gamma                90
_cell_volume                     664.47(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5846
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      30.76

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   0.6890
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          1.200
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7384
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.865
_diffrn_reflns_theta_max         30.885
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3779
_reflns_number_gt                3688
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_max     0.853
_reflns_Friedel_fraction_full    0.985

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0399P)²+0.1075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3779
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0714
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.076
_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 0.01136(4) 1.00254(5) 0.87287(3) 0.01310(9) Uani 1 1 d . . . . .
O1 O -0.01922(13) 1.0136(2) 0.99906(10) 0.0205(2) Uani 1 1 d . . . . .
O2 O -0.05093(15) 1.14255(18) 0.78765(12) 0.0209(3) Uani 1 1 d . . . . .
N1 N -0.06279(16) 0.8050(2) 0.82531(12) 0.0140(2) Uani 1 1 d . . . . .
H4 H -0.0958 0.7276 0.8788 0.017 Uiso 1 1 calc R U . . .
C1 C 0.5425(2) 0.9508(3) 0.8624(3) 0.0366(5) Uani 1 1 d . . . . .
H1 H 0.6536 0.9362 0.8587 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4751(2) 0.8856(3) 0.9639(2) 0.0313(5) Uani 1 1 d . . . . .
H15 H 0.5403 0.8279 1.0295 0.038 Uiso 1 1 calc R U . . .
C3 C 0.3126(2) 0.9052(3) 0.96896(17) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.2652 0.8600 1.0374 0.026 Uiso 1 1 calc R U . . .
C4 C 0.21980(16) 0.9922(3) 0.87198(13) 0.0153(3) Uani 1 1 d . . . . .
C5 C -0.07690(18) 0.7504(2) 0.69527(14) 0.0156(3) Uani 1 1 d . . . . .
H5 H -0.1153 0.8606 0.6449 0.019 Uiso 1 1 calc R U . . .
C6 C 0.07805(18) 0.6841(2) 0.65165(14) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.19077(19) 0.5814(2) 0.72682(14) 0.0173(3) Uani 1 1 d . . . . .
H9 H 0.1718 0.5518 0.8080 0.021 Uiso 1 1 calc R U . . .
C8 C 0.33047(19) 0.5220(3) 0.68381(15) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.4076 0.4550 0.7364 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3579(2) 0.5606(3) 0.56376(16) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.4530 0.5191 0.5342 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2452(2) 0.6599(3) 0.48780(15) 0.0197(3) Uani 1 1 d . . . . .
H6 H 0.2626 0.6852 0.4056 0.024 Uiso 1 1 calc R U . . .
C11 C 0.10683(19) 0.7226(2) 0.53186(14) 0.0174(3) Uani 1 1 d . . . . .
H7 H 0.0312 0.7924 0.4798 0.021 Uiso 1 1 calc R U . . .
C12 C -0.2055(2) 0.5999(3) 0.67660(19) 0.0259(4) Uani 1 1 d . . . . .
H12 H -0.1703 0.4903 0.7252 0.039 Uiso 1 1 calc R U . . .
H11 H -0.2236 0.5660 0.5898 0.039 Uiso 1 1 calc R U . . .
H10 H -0.3049 0.6470 0.7029 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2861(2) 1.0593(3) 0.77050(17) 0.0232(3) Uani 1 1 d . . . . .
H14 H 0.2215 1.1191 0.7055 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4487(2) 1.0368(3) 0.7666(2) 0.0344(5) Uani 1 1 d . . . . .
H13 H 0.4960 1.0807 0.6978 0.041 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 O2 1.4339(13) . ?
S1 O1 1.4435(12) . ?
S1 N1 1.6166(14) . ?
S1 C4 1.7632(14) . ?
N1 C5 1.474(2) . ?
N1 H4 0.8800 . ?
C1 C14 1.388(4) . ?
C1 C2 1.393(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(3) . ?
C2 H15 0.9500 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9500 . ?
C4 C13 1.393(2) . ?
C5 C6 1.523(2) . ?
C5 C12 1.531(2) . ?
C5 H5 1.0000 . ?
C6 C11 1.395(2) . ?
C6 C7 1.397(2) . ?
C7 C8 1.389(2) . ?
C7 H9 0.9500 . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H2 0.9500 . ?
C10 C11 1.392(2) . ?
C10 H6 0.9500 . ?
C11 H7 0.9500 . ?
C12 H12 0.9800 . ?
C12 H11 0.9800 . ?
C12 H10 0.9800 . ?
C13 C14 1.388(3) . ?
C13 H14 0.9500 . ?
C14 H13 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
O2 S1 O1 119.74(8) . . ?
O2 S1 N1 108.06(8) . . ?
O1 S1 N1 104.65(8) . . ?
O2 S1 C4 108.39(8) . . ?
O1 S1 C4 107.46(7) . . ?
N1 S1 C4 108.04(8) . . ?
C5 N1 S1 122.17(12) . . ?
C5 N1 H4 118.9 . . ?
S1 N1 H4 118.9 . . ?
C14 C1 C2 120.54(18) . . ?
C14 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.89(19) . . ?
C3 C2 H15 120.1 . . ?
C1 C2 H15 120.1 . . ?
C2 C3 C4 118.91(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C13 C4 C3 121.73(15) . . ?
C13 C4 S1 119.07(12) . . ?
C3 C4 S1 119.04(12) . . ?
N1 C5 C6 114.55(12) . . ?
N1 C5 C12 107.08(14) . . ?
C6 C5 C12 110.95(14) . . ?
N1 C5 H5 108.0 . . ?
C6 C5 H5 108.0 . . ?
C12 C5 H5 108.0 . . ?
C11 C6 C7 118.77(14) . . ?
C11 C6 C5 119.14(14) . . ?
C7 C6 C5 122.06(14) . . ?
C8 C7 C6 120.55(15) . . ?
C8 C7 H9 119.7 . . ?
C6 C7 H9 119.7 . . ?
C7 C8 C9 120.25(15) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.56(15) . . ?
C10 C9 H2 120.2 . . ?
C8 C9 H2 120.2 . . ?
C9 C10 C11 120.11(15) . . ?
C9 C10 H6 119.9 . . ?
C11 C10 H6 119.9 . . ?
C10 C11 C6 120.74(15) . . ?
C10 C11 H7 119.6 . . ?
C6 C11 H7 119.6 . . ?
C5 C12 H12 109.5 . . ?
C5 C12 H11 109.5 . . ?
H12 C12 H11 109.5 . . ?
C5 C12 H10 109.5 . . ?
H12 C12 H10 109.5 . . ?
H11 C12 H10 109.5 . . ?
C14 C13 C4 118.51(18) . . ?
C14 C13 H14 120.7 . . ?
C4 C13 H14 120.7 . . ?
C1 C14 C13 120.42(19) . . ?
C1 C14 H13 119.8 . . ?
C13 C14 H13 119.8 . . ?

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 S1 N1 C5 42.60(14) . . . . ?
O1 S1 N1 C5 171.24(12) . . . . ?
C4 S1 N1 C5 -74.47(13) . . . . ?
C14 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C13 0.1(3) . . . . ?
C2 C3 C4 S1 175.51(15) . . . . ?
O2 S1 C4 C13 -21.82(18) . . . . ?
O1 S1 C4 C13 -152.55(15) . . . . ?
N1 S1 C4 C13 95.04(16) . . . . ?
O2 S1 C4 C3 162.69(14) . . . . ?
O1 S1 C4 C3 31.96(17) . . . . ?
N1 S1 C4 C3 -80.46(15) . . . . ?
S1 N1 C5 C6 78.20(16) . . . . ?
S1 N1 C5 C12 -158.32(12) . . . . ?
N1 C5 C6 C11 -145.80(15) . . . . ?
C12 C5 C6 C11 92.83(18) . . . . ?
N1 C5 C6 C7 35.9(2) . . . . ?
C12 C5 C6 C7 -85.43(19) . . . . ?
C11 C6 C7 C8 1.3(3) . . . . ?
C5 C6 C7 C8 179.59(16) . . . . ?
C6 C7 C8 C9 -1.6(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C6 -1.1(3) . . . . ?
C7 C6 C11 C10 0.0(2) . . . . ?
C5 C6 C11 C10 -178.30(15) . . . . ?
C3 C4 C13 C14 0.5(3) . . . . ?
S1 C4 C13 C14 -174.89(15) . . . . ?
C2 C1 C14 C13 0.0(3) . . . . ?
C4 C13 C14 C1 -0.6(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
N1 H4 O1 0.88 2.19 2.882(2) 134.6 2_547
N1 H4 O1 0.88 2.19 2.882(2) 134.6 2_547
N1 H4 O1 0.88 2.19 2.882(2) 134.6 2_547
N1 H4 O1 0.88 2.19 2.882(2) 134.6 2_547
N1 H4 O1 0.88 2.19 2.882(2) 134.6 2_547
N1 H4 O1 0.88 2.19 2.882(2) 134.6 2_547
N1 H4 O1 0.88 2.19 2.882(2) 134.6 2_547
N1 H4 O1 0.88 2.19 2.882(2) 134.6 2_547

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.065

