# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1483507'
_audit_update_record             
;
2016-06-05 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N3 O S'
_chemical_formula_weight         271.33

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      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                   7.680(5)
_cell_length_b                   8.494(5)
_cell_length_c                   11.449(7)
_cell_angle_alpha                85.960(7)
_cell_angle_beta                 77.314(7)
_cell_angle_gamma                66.467(7)
_cell_volume                     667.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1593
_cell_measurement_theta_min      2.619
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.986
_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 Smart Aepex CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5029
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.823
_diffrn_reflns_theta_max         26.766
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2544
_reflns_number_gt                1906
_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-2013 (Sheldrick, 2013)'
_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)+(0.1184P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2544
_refine_ls_number_parameters     174
_refine_ls_number_restraints     280
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.172
_refine_ls_shift/su_mean         0.006

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 0.0964(3) 0.1559(3) 0.58933(18) 0.0419(5) Uani 1 1 d . U . . .
C2 C 0.0067(3) 0.2772(3) 0.5124(2) 0.0510(5) Uani 1 1 d . U . . .
H2 H -0.0908 0.3816 0.5423 0.061 Uiso 1 1 calc R U . . .
C3 C 0.0620(3) 0.2437(3) 0.3888(2) 0.0526(5) Uani 1 1 d . U . . .
H3 H 0.0008 0.3276 0.3378 0.063 Uiso 1 1 calc R U . . .
C4 C 0.2019(3) 0.0929(3) 0.34132(18) 0.0466(5) Uani 1 1 d . U . . .
C5 C 0.2999(3) -0.0380(3) 0.41714(18) 0.0423(5) Uani 1 1 d . U . . .
C6 C 0.2471(3) -0.0035(3) 0.54205(18) 0.0412(5) Uani 1 1 d . U . . .
C7 C 0.4483(3) -0.1980(3) 0.3774(2) 0.0527(6) Uani 1 1 d . U . . .
H7 H 0.4873 -0.2271 0.2963 0.063 Uiso 1 1 calc R U . . .
C8 C 0.5346(3) -0.3101(3) 0.4587(2) 0.0573(6) Uani 1 1 d . U . . .
H8 H 0.6331 -0.4163 0.4335 0.069 Uiso 1 1 calc R U . . .
C9 C 0.4741(3) -0.2643(3) 0.5797(2) 0.0559(6) Uani 1 1 d . U . . .
H9 H 0.5363 -0.3419 0.6336 0.067 Uiso 1 1 calc R U . . .
C10 C 0.4751(4) 0.0499(3) 0.14041(19) 0.0607(6) Uani 1 1 d . U . . .
C11 C -0.0863(4) 0.3103(3) 0.7827(2) 0.0586(6) Uani 1 1 d . U . . .
C12 C -0.0941(5) 0.2897(3) 0.9155(2) 0.0749(8) Uani 1 1 d . U . . .
H12A H -0.1319 0.1948 0.9422 0.090 Uiso 1 1 calc R U . . .
H12B H 0.0350 0.2604 0.9299 0.090 Uiso 1 1 calc R U . . .
C13 C -0.2297(5) 0.4439(5) 0.9872(3) 0.1011(11) Uani 1 1 d . U . . .
H13A H -0.3571 0.4763 0.9693 0.121 Uiso 1 1 calc R U . . .
H13B H -0.1879 0.5371 0.9627 0.121 Uiso 1 1 calc R U . . .
C14 C -0.2478(5) 0.4244(5) 1.1206(3) 0.0964(10) Uani 1 1 d . U . . .
H14A H -0.2640 0.3195 1.1440 0.145 Uiso 1 1 calc R U . . .
H14B H -0.3584 0.5198 1.1609 0.145 Uiso 1 1 calc R U . . .
H14C H -0.1325 0.4215 1.1420 0.145 Uiso 1 1 calc R U . . .
N1 N 0.6302(4) 0.0390(4) 0.1064(2) 0.0880(8) Uani 1 1 d . U . . .
N2 N 0.3341(3) -0.1178(2) 0.62230(16) 0.0480(5) Uani 1 1 d . U . . .
N3 N 0.0548(3) 0.1758(2) 0.71380(15) 0.0503(5) Uani 1 1 d . U . . .
H3A H 0.1412 0.0830 0.7475 0.060 Uiso 1 1 d R U . . .
O1 O -0.1975(3) 0.4356(2) 0.74022(17) 0.0914(7) Uani 1 1 d . U . . .
S1 S 0.24688(9) 0.05669(9) 0.18352(5) 0.0642(3) Uani 1 1 d . 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
C1 C2 1.372(3) . ?
C1 N3 1.397(3) . ?
C1 C6 1.429(3) . ?
C2 C3 1.400(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.428(3) . ?
C4 S1 1.788(2) . ?
C5 C7 1.406(3) . ?
C5 C6 1.416(3) . ?
C6 N2 1.363(3) . ?
C7 C8 1.361(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(4) . ?
C8 H8 0.9300 . ?
C9 N2 1.315(3) . ?
C9 H9 0.9300 . ?
C10 N1 1.137(3) . ?
C10 S1 1.692(3) . ?
C11 O1 1.218(3) . ?
C11 N3 1.365(3) . ?
C11 C12 1.509(4) . ?
C12 C13 1.470(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.506(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N3 H3A 0.9288 . ?

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 N3 125.00(19) . . ?
C2 C1 C6 119.43(18) . . ?
N3 C1 C6 115.56(17) . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 120.39(19) . . ?
C3 C4 S1 118.25(17) . . ?
C5 C4 S1 121.19(16) . . ?
C4 C5 C7 125.12(19) . . ?
C4 C5 C6 117.81(18) . . ?
C7 C5 C6 117.05(19) . . ?
N2 C6 C5 122.70(18) . . ?
N2 C6 C1 116.98(18) . . ?
C5 C6 C1 120.33(18) . . ?
C8 C7 C5 119.5(2) . . ?
C8 C7 H7 120.3 . . ?
C5 C7 H7 120.3 . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
N2 C9 C8 123.9(2) . . ?
N2 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
N1 C10 S1 176.1(2) . . ?
O1 C11 N3 122.6(2) . . ?
O1 C11 C12 122.9(2) . . ?
N3 C11 C12 114.5(2) . . ?
C13 C12 C11 113.8(3) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 115.0(3) . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 N2 C6 117.49(19) . . ?
C11 N3 C1 128.0(2) . . ?
C11 N3 H3A 121.4 . . ?
C1 N3 H3A 110.6 . . ?
C10 S1 C4 100.99(10) . . ?

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
N3 C1 C2 C3 179.26(19) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 C4 S1 174.83(17) . . . . ?
C3 C4 C5 C7 -179.3(2) . . . . ?
S1 C4 C5 C7 5.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
S1 C4 C5 C6 -175.88(14) . . . . ?
C4 C5 C6 N2 -178.59(18) . . . . ?
C7 C5 C6 N2 0.2(3) . . . . ?
C4 C5 C6 C1 1.7(3) . . . . ?
C7 C5 C6 C1 -179.50(18) . . . . ?
C2 C1 C6 N2 178.60(19) . . . . ?
N3 C1 C6 N2 -0.3(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
N3 C1 C6 C5 179.44(16) . . . . ?
C4 C5 C7 C8 178.0(2) . . . . ?
C6 C5 C7 C8 -0.7(3) . . . . ?
C5 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 N2 1.0(4) . . . . ?
O1 C11 C12 C13 -7.8(5) . . . . ?
N3 C11 C12 C13 172.8(3) . . . . ?
C11 C12 C13 C14 177.2(3) . . . . ?
C8 C9 N2 C6 -1.5(3) . . . . ?
C5 C6 N2 C9 0.9(3) . . . . ?
C1 C6 N2 C9 -179.45(19) . . . . ?
O1 C11 N3 C1 -0.4(4) . . . . ?
C12 C11 N3 C1 179.0(2) . . . . ?
C2 C1 N3 C11 4.3(4) . . . . ?
C6 C1 N3 C11 -176.9(2) . . . . ?
C3 C4 S1 C10 114.4(2) . . . . ?
C5 C4 S1 C10 -70.23(19) . . . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-2



