# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_mo_fs419_0m
_database_code_depnum_ccdc_archive 'CCDC 1479814'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 N3 O2 S'
_chemical_formula_sum            'C14 H7 N3 O2 S'
_chemical_formula_weight         281.29

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                   7.5691(9)
_cell_length_b                   8.3593(10)
_cell_length_c                   10.1479(12)
_cell_angle_alpha                83.336(2)
_cell_angle_beta                 88.008(2)
_cell_angle_gamma                67.0850(10)
_cell_volume                     587.38(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5298
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      27.74
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'

_exptl_special_details           
; 
The crystal was placed in the cold stream of an Oxford Cryosystems 
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating 
at 100 K.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker SMART APEX II DUO CCD area-detector diffractometer 
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8048
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.021
_diffrn_reflns_theta_max         27.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2728
_reflns_number_gt                2434
_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       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.0384P)²+0.3240P] 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         2728
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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
_geom_hbond_publ_flag

C4 H4A N3 0.9500 2.5900 3.349(2) 137.00 1_546 yes
C5 H5A O1 0.9500 2.5600 3.357(2) 141.00 1_545 yes
C12 H12A O2 0.9500 2.5500 3.359(2) 143.00 2_675 yes
C14 H14A O1 0.9500 2.4300 3.335(2) 159.00 2_676 yes


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 0.96966(5) 0.73241(5) -0.07820(4) 0.01836(12) Uani 1 1 d . . . . .
O1 O 0.75676(15) 0.81680(14) 0.50741(11) 0.0184(2) Uani 1 1 d . . . . .
O2 O 0.62109(15) 0.52671(14) 0.19250(11) 0.0179(2) Uani 1 1 d . . . . .
N1 N 0.69341(17) 0.70594(16) 0.32235(12) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.89445(18) 0.67982(16) 0.06545(12) 0.0156(3) Uani 1 1 d . . . . .
N3 N 0.85374(19) 0.94190(17) -0.09551(13) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.7413(2) 0.69882(19) 0.45681(15) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.7666(2) 0.52137(19) 0.51805(15) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.8172(2) 0.4453(2) 0.64713(15) 0.0166(3) Uani 1 1 d . . . . .
H3A H 0.8411 0.5073 0.7124 0.020 Uiso 1 1 calc R U . . .
C4 C 0.8315(2) 0.2734(2) 0.67701(15) 0.0185(3) Uani 1 1 d . . . . .
H4A H 0.8644 0.2175 0.7648 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7985(2) 0.1820(2) 0.58074(16) 0.0193(3) Uani 1 1 d . . . . .
H5A H 0.8111 0.0646 0.6038 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7472(2) 0.25999(19) 0.45077(16) 0.0174(3) Uani 1 1 d . . . . .
H6A H 0.7242 0.1981 0.3849 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7313(2) 0.43124(19) 0.42198(15) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.6753(2) 0.55008(19) 0.29610(15) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.6662(2) 0.85216(19) 0.22738(15) 0.0143(3) Uani 1 1 d . . . . .
C10 C 0.7701(2) 0.83061(19) 0.10593(15) 0.0142(3) Uani 1 1 d . . . . .
C11 C 0.7467(2) 0.98154(19) 0.01401(15) 0.0156(3) Uani 1 1 d . . . . .
C12 C 0.6241(2) 1.15172(19) 0.04229(16) 0.0177(3) Uani 1 1 d . . . . .
H12A H 0.6089 1.2518 -0.0183 0.021 Uiso 1 1 calc R U . . .
C13 C 0.5292(2) 1.16600(19) 0.15951(16) 0.0182(3) Uani 1 1 d . . . . .
H13A H 0.4475 1.2788 0.1808 0.022 Uiso 1 1 calc R U . . .
C14 C 0.5480(2) 1.01748(19) 0.25163(15) 0.0169(3) Uani 1 1 d . . . . .
H14A H 0.4769 1.0338 0.3315 0.020 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 N3 1.6156(14) . ?
S1 N2 1.6220(13) . ?
O1 C1 1.2091(18) . ?
O2 C8 1.2049(18) . ?
N1 C1 1.4125(19) . ?
N1 C8 1.4175(18) . ?
N1 C9 1.4177(19) . ?
N2 C10 1.3465(19) . ?
N3 C11 1.347(2) . ?
C1 C2 1.482(2) . ?
C2 C3 1.385(2) . ?
C2 C7 1.391(2) . ?
C3 C4 1.396(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.398(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.488(2) . ?
C9 C14 1.368(2) . ?
C9 C10 1.429(2) . ?
C10 C11 1.434(2) . ?
C11 C12 1.420(2) . ?
C12 C13 1.361(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.427(2) . ?
C13 H13A 0.9500 . ?
C14 H14A 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
N3 S1 N2 101.00(7) . . ?
C1 N1 C8 111.39(12) . . ?
C1 N1 C9 123.55(12) . . ?
C8 N1 C9 125.05(12) . . ?
C10 N2 S1 105.91(10) . . ?
C11 N3 S1 106.56(10) . . ?
O1 C1 N1 125.24(14) . . ?
O1 C1 C2 128.97(14) . . ?
N1 C1 C2 105.80(12) . . ?
C3 C2 C7 121.75(14) . . ?
C3 C2 C1 129.58(13) . . ?
C7 C2 C1 108.67(13) . . ?
C2 C3 C4 117.06(14) . . ?
C2 C3 H3A 121.5 . . ?
C4 C3 H3A 121.5 . . ?
C5 C4 C3 121.36(14) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 121.16(14) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C7 C6 C5 117.25(14) . . ?
C7 C6 H6A 121.4 . . ?
C5 C6 H6A 121.4 . . ?
C6 C7 C2 121.42(14) . . ?
C6 C7 C8 130.08(14) . . ?
C2 C7 C8 108.50(12) . . ?
O2 C8 N1 125.15(14) . . ?
O2 C8 C7 129.39(13) . . ?
N1 C8 C7 105.44(12) . . ?
C14 C9 N1 121.31(13) . . ?
C14 C9 C10 118.32(13) . . ?
N1 C9 C10 120.30(13) . . ?
N2 C10 C9 127.02(13) . . ?
N2 C10 C11 113.69(13) . . ?
C9 C10 C11 119.28(13) . . ?
N3 C11 C12 125.99(14) . . ?
N3 C11 C10 112.82(13) . . ?
C12 C11 C10 121.17(14) . . ?
C13 C12 C11 117.47(14) . . ?
C13 C12 H12A 121.3 . . ?
C11 C12 H12A 121.3 . . ?
C12 C13 C14 122.35(14) . . ?
C12 C13 H13A 118.8 . . ?
C14 C13 H13A 118.8 . . ?
C9 C14 C13 121.39(14) . . ?
C9 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-3

