# 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_2015572_0ma.CIF
_database_code_depnum_ccdc_archive 'CCDC 1439142'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            work
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16H12 N2 O S'
_chemical_formula_weight         280.34

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2154(2)
_cell_length_b                   9.4198(2)
_cell_length_c                   10.4296(3)
_cell_angle_alpha                76.342(2)
_cell_angle_beta                 79.372(2)
_cell_angle_gamma                84.6420(10)
_cell_volume                     676.09(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      25.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      1.377
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7990
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(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 APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10057
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2511
_reflns_number_gt                2152
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.4126P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0.0039(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2511
_refine_ls_number_parameters     181
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.11562(8) -0.02943(6) 0.71476(6) 0.03522(19) Uani 1 1 d . . .
O1 O -0.0269(2) 0.44492(16) 0.84358(16) 0.0409(4) Uani 1 1 d . . .
N2 N 0.0438(2) 0.21721(17) 0.80287(16) 0.0243(4) Uani 1 1 d . . .
C14 C 0.6270(3) -0.3472(3) 0.7455(3) 0.0447(6) Uani 1 1 d . . .
H14 H 0.7314 -0.4130 0.7488 0.054 Uiso 1 1 calc R . .
C13 C 0.4514(4) -0.3925(3) 0.8106(2) 0.0450(6) Uani 1 1 d . . .
H13 H 0.4383 -0.4887 0.8586 0.054 Uiso 1 1 calc R . .
C12 C 0.2934(3) -0.2959(2) 0.8053(2) 0.0347(5) Uani 1 1 d . . .
H12 H 0.1749 -0.3267 0.8494 0.042 Uiso 1 1 calc R . .
C11 C 0.3158(3) -0.1531(2) 0.7333(2) 0.0277(4) Uani 1 1 d . . .
C10 C 0.1415(3) 0.0829(2) 0.82360(19) 0.0256(4) Uani 1 1 d . . .
C5 C -0.0862(3) 0.2539(2) 0.70774(19) 0.0236(4) Uani 1 1 d U . .
C4 C -0.2679(3) 0.2306(2) 0.7572(2) 0.0264(4) Uani 1 1 d U . .
H4 H -0.3080 0.1896 0.8473 0.032 Uiso 1 1 calc R . .
C3 C -0.3914(3) 0.2699(2) 0.6694(2) 0.0359(5) Uani 1 1 d U . .
H3 H -0.5194 0.2572 0.7007 0.043 Uiso 1 1 calc R . .
C2 C -0.3325(3) 0.3277(2) 0.5362(2) 0.0352(5) Uani 1 1 d . . .
H2 H -0.4188 0.3528 0.4773 0.042 Uiso 1 1 calc R . .
C6 C 0.0573(3) 0.3252(2) 0.8738(2) 0.0295(5) Uani 1 1 d . . .
C7 C 0.1722(3) 0.2821(2) 0.9762(2) 0.0326(5) Uani 1 1 d . . .
H7 H 0.1860 0.3476 1.0277 0.039 Uiso 1 1 calc R . .
C8 C 0.2607(3) 0.1482(2) 0.9993(2) 0.0327(5) Uani 1 1 d . . .
H8 H 0.3314 0.1223 1.0682 0.039 Uiso 1 1 calc R . .
C9 C 0.2486(3) 0.0466(2) 0.9219(2) 0.0308(5) Uani 1 1 d . . .
H9 H 0.3133 -0.0443 0.9380 0.037 Uiso 1 1 calc R . .
C1 C -0.1437(3) 0.3478(3) 0.4912(2) 0.0381(5) Uani 1 1 d . . .
H1 H -0.1017 0.3870 0.4010 0.046 Uiso 1 1 calc R . .
N1 N -0.0158(3) 0.3108(2) 0.57800(19) 0.0408(5) Uani 1 1 d U . .
C16 C 0.4931(3) -0.1067(2) 0.6686(2) 0.0336(5) Uani 1 1 d . . .
H16 H 0.5073 -0.0105 0.6209 0.040 Uiso 1 1 calc R . .
C15 C 0.6484(3) -0.2044(3) 0.6755(3) 0.0433(6) Uani 1 1 d . . .
H15 H 0.7675 -0.1737 0.6329 0.052 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
S1 C10 1.768(2) . ?
S1 C11 1.778(2) . ?
O1 C6 1.231(2) . ?
N2 C10 1.381(2) . ?
N2 C6 1.412(3) . ?
N2 C5 1.450(2) . ?
C14 C13 1.377(4) . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.392(3) . ?
C13 H13 0.9300 . ?
C12 C11 1.385(3) . ?
C12 H12 0.9300 . ?
C11 C16 1.389(3) . ?
C10 C9 1.358(3) . ?
C5 C4 1.336(3) . ?
C5 N1 1.353(3) . ?
C4 C3 1.360(3) . ?
C4 H4 0.9300 . ?
C3 C2 1.370(3) . ?
C3 H3 0.9300 . ?
C2 C1 1.372(3) . ?
C2 H2 0.9300 . ?
C6 C7 1.432(3) . ?
C7 C8 1.350(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.407(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C1 N1 1.375(3) . ?
C1 H1 0.9300 . ?
C16 C15 1.383(3) . ?
C16 H16 0.9300 . ?
C15 H15 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 C11 100.54(9) . . ?
C10 N2 C6 123.36(16) . . ?
C10 N2 C5 121.02(16) . . ?
C6 N2 C5 115.59(15) . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C11 C12 C13 118.8(2) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C11 C16 120.60(19) . . ?
C12 C11 S1 120.25(16) . . ?
C16 C11 S1 119.06(16) . . ?
C9 C10 N2 119.61(18) . . ?
C9 C10 S1 125.07(16) . . ?
N2 C10 S1 115.32(14) . . ?
C4 C5 N1 125.40(18) . . ?
C4 C5 N2 116.43(17) . . ?
N1 C5 N2 118.16(17) . . ?
C5 C4 C3 116.71(19) . . ?
C5 C4 H4 121.6 . . ?
C3 C4 H4 121.6 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
O1 C6 N2 118.89(18) . . ?
O1 C6 C7 126.21(19) . . ?
N2 C6 C7 114.91(17) . . ?
C8 C7 C6 121.07(19) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.72(19) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C9 C8 119.19(19) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N1 C1 C2 120.8(2) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C5 N1 C1 116.59(19) . . ?
C15 C16 C11 119.7(2) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?

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
C15 C14 C13 C12 0.8(4) . . . . ?
C14 C13 C12 C11 0.0(3) . . . . ?
C13 C12 C11 C16 -0.6(3) . . . . ?
C13 C12 C11 S1 175.84(16) . . . . ?
C10 S1 C11 C12 106.64(17) . . . . ?
C10 S1 C11 C16 -76.83(17) . . . . ?
C6 N2 C10 C9 4.0(3) . . . . ?
C5 N2 C10 C9 -173.93(18) . . . . ?
C6 N2 C10 S1 -175.58(15) . . . . ?
C5 N2 C10 S1 6.5(2) . . . . ?
C11 S1 C10 C9 -18.8(2) . . . . ?
C11 S1 C10 N2 160.81(15) . . . . ?
C10 N2 C5 C4 95.0(2) . . . . ?
C6 N2 C5 C4 -83.1(2) . . . . ?
C10 N2 C5 N1 -86.2(2) . . . . ?
C6 N2 C5 N1 95.7(2) . . . . ?
N1 C5 C4 C3 -1.1(3) . . . . ?
N2 C5 C4 C3 177.61(18) . . . . ?
C5 C4 C3 C2 1.3(3) . . . . ?
C4 C3 C2 C1 -0.8(3) . . . . ?
C10 N2 C6 O1 176.05(19) . . . . ?
C5 N2 C6 O1 -5.9(3) . . . . ?
C10 N2 C6 C7 -3.7(3) . . . . ?
C5 N2 C6 C7 174.32(17) . . . . ?
O1 C6 C7 C8 -179.0(2) . . . . ?
N2 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 1.8(3) . . . . ?
N2 C10 C9 C8 -1.2(3) . . . . ?
S1 C10 C9 C8 178.36(15) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C3 C2 C1 N1 0.0(3) . . . . ?
C4 C5 N1 C1 0.3(3) . . . . ?
N2 C5 N1 C1 -178.33(18) . . . . ?
C2 C1 N1 C5 0.2(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
S1 C11 C16 C15 -176.09(16) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C11 C16 C15 C14 0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.050
