# 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 2017

####################################################################### 
# 
# 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_za2
_database_code_depnum_ccdc_archive 'CCDC 1555176'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2017-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Cl N S'
_chemical_formula_weight         259.74

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.4123(5)
_cell_length_b                   5.7309(2)
_cell_length_c                   16.0699(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.8380(10)
_cell_angle_gamma                90.00
_cell_volume                     1214.07(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      26.41

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9342
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8076
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.60
_reflns_number_total             4530
_reflns_number_gt                4401
_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)+(0.0638P)²+0.0000P] 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       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_number_reflns         4530
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65023(13) 0.2763(4) 0.43925(11) 0.0242(4) Uani 1 1 d . . .
H1A H 0.6571 0.3274 0.3871 0.029 Uiso 1 1 calc R . .
C2 C 0.68986(11) 0.0752(3) 0.48446(11) 0.0202(3) Uani 1 1 d . . .
C3 C 0.66212(11) 0.0643(3) 0.56110(10) 0.0175(3) Uani 1 1 d . . .
C4 C 0.68218(11) -0.0929(3) 0.63278(11) 0.0189(3) Uani 1 1 d . . .
H4A H 0.7188 -0.2288 0.6362 0.023 Uiso 1 1 calc R . .
C5 C 0.64638(11) -0.0417(3) 0.69852(11) 0.0224(4) Uani 1 1 d . . .
H5A H 0.6589 -0.1449 0.7465 0.027 Uiso 1 1 calc R . .
C6 C 0.59138(12) 0.1639(4) 0.69392(12) 0.0250(4) Uani 1 1 d . . .
H6A H 0.5689 0.1945 0.7395 0.030 Uiso 1 1 calc R . .
C7 C 0.56990(12) 0.3211(3) 0.62394(12) 0.0230(4) Uani 1 1 d . . .
H7A H 0.5328 0.4560 0.6209 0.028 Uiso 1 1 calc R . .
C8 C 0.60628(12) 0.2688(3) 0.55767(11) 0.0190(3) Uani 1 1 d . . .
C9 C 0.88237(12) -0.1074(3) 0.53964(10) 0.0177(3) Uani 1 1 d . . .
C10 C 0.95073(13) -0.2886(3) 0.54760(11) 0.0209(4) Uani 1 1 d . . .
H10A H 0.9294 -0.4183 0.5098 0.025 Uiso 1 1 calc R . .
C11 C 1.04994(13) -0.2750(3) 0.61157(11) 0.0213(4) Uani 1 1 d . . .
H11A H 1.0955 -0.3949 0.6170 0.026 Uiso 1 1 calc R . .
C12 C 1.08047(12) -0.0800(3) 0.66745(11) 0.0190(3) Uani 1 1 d . . .
C13 C 1.01402(12) 0.0985(3) 0.66182(11) 0.0194(3) Uani 1 1 d . . .
H13A H 1.0353 0.2264 0.7006 0.023 Uiso 1 1 calc R . .
C14 C 0.91432(12) 0.0840(3) 0.59697(11) 0.0187(3) Uani 1 1 d . . .
H14A H 0.8689 0.2038 0.5922 0.022 Uiso 1 1 calc R . .
C15 C 0.14384(14) 0.1762(3) 1.02188(12) 0.0256(4) Uani 1 1 d . . .
H15A H 0.1918 0.1093 1.0744 0.031 Uiso 1 1 calc R . .
C16 C 0.15388(12) 0.3864(3) 0.98648(11) 0.0198(3) Uani 1 1 d . . .
C17 C 0.06376(11) 0.4217(3) 0.90499(10) 0.0166(3) Uani 1 1 d . . .
C18 C 0.02884(12) 0.6015(3) 0.84064(11) 0.0186(3) Uani 1 1 d . . .
H18A H 0.0693 0.7304 0.8438 0.022 Uiso 1 1 calc R . .
C19 C -0.06734(12) 0.5821(3) 0.77242(11) 0.0217(3) Uani 1 1 d . . .
H19A H -0.0917 0.7004 0.7294 0.026 Uiso 1 1 calc R . .
C20 C -0.12942(13) 0.3877(3) 0.76636(12) 0.0251(4) Uani 1 1 d . . .
H20A H -0.1944 0.3818 0.7204 0.030 Uiso 1 1 calc R . .
C21 C -0.09570(13) 0.2069(3) 0.82717(12) 0.0250(4) Uani 1 1 d . . .
H21A H -0.1363 0.0773 0.8226 0.030 Uiso 1 1 calc R . .
C22 C 0.00111(13) 0.2238(3) 0.89579(11) 0.0204(4) Uani 1 1 d . . .
C23 C 0.31536(11) 0.6043(3) 0.96648(11) 0.0186(3) Uani 1 1 d . . .
C24 C 0.30873(12) 0.4309(3) 0.90327(11) 0.0202(3) Uani 1 1 d . . .
H24A H 0.2667 0.3026 0.8963 0.024 Uiso 1 1 calc R . .
C25 C 0.36475(12) 0.4498(3) 0.85088(11) 0.0219(3) Uani 1 1 d . . .
H25A H 0.3604 0.3356 0.8083 0.026 Uiso 1 1 calc R . .
C26 C 0.42718(12) 0.6412(3) 0.86286(11) 0.0234(4) Uani 1 1 d . . .
C27 C 0.43382(13) 0.8148(3) 0.92410(12) 0.0240(4) Uani 1 1 d . . .
H27A H 0.4760 0.9427 0.9309 0.029 Uiso 1 1 calc R . .
C28 C 0.37648(12) 0.7964(3) 0.97568(11) 0.0228(4) Uani 1 1 d . . .
H28A H 0.3793 0.9141 1.0165 0.027 Uiso 1 1 calc R . .
N1 N 0.59896(10) 0.3918(3) 0.48150(10) 0.0255(3) Uani 1 1 d . . .
H1 H 0.5670 0.5214 0.4635 0.031 Uiso 1 1 calc R . .
N2 N 0.05267(11) 0.0791(3) 0.96856(10) 0.0269(3) Uani 1 1 d . . .
H2 H 0.0306 -0.0526 0.9788 0.032 Uiso 1 1 calc R . .
S1 S 0.75786(3) -0.13482(8) 0.45303(3) 0.02323(11) Uani 1 1 d . . .
Cl1 Cl 1.20554(3) -0.06405(9) 0.74700(3) 0.02960(12) Uani 1 1 d . . .
S3 S 0.25133(3) 0.58641(8) 1.04004(3) 0.02264(11) Uani 1 1 d . . .
Cl2 Cl 0.49971(3) 0.66400(10) 0.79869(3) 0.03549(13) 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
C1 C2 1.359(3) . ?
C1 N1 1.360(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.442(2) . ?
C2 S1 1.7504(18) . ?
C3 C4 1.398(2) . ?
C3 C8 1.410(2) . ?
C4 C5 1.382(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.405(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.375(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.396(2) . ?
C7 H7A 0.9300 . ?
C8 N1 1.379(2) . ?
C9 C14 1.386(2) . ?
C9 C10 1.401(2) . ?
C9 S1 1.7785(16) . ?
C10 C11 1.385(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.379(2) . ?
C12 Cl1 1.7404(16) . ?
C13 C14 1.395(2) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 N2 1.364(2) . ?
C15 C16 1.365(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.438(2) . ?
C16 S3 1.7465(18) . ?
C17 C18 1.401(2) . ?
C17 C22 1.420(2) . ?
C18 C19 1.381(2) . ?
C18 H18A 0.9300 . ?
C19 C20 1.407(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.371(3) . ?
C20 H20A 0.9300 . ?
C21 C22 1.389(3) . ?
C21 H21A 0.9300 . ?
C22 N2 1.380(2) . ?
C23 C28 1.380(3) . ?
C23 C24 1.397(2) . ?
C23 S3 1.7724(16) . ?
C24 C25 1.386(2) . ?
C24 H24A 0.9300 . ?
C25 C26 1.382(3) . ?
C25 H25A 0.9300 . ?
C26 C27 1.375(3) . ?
C26 Cl2 1.7449(17) . ?
C27 C28 1.391(3) . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?

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 N1 109.98(15) . . ?
C2 C1 H1A 125.0 . . ?
N1 C1 H1A 125.0 . . ?
C1 C2 C3 106.94(15) . . ?
C1 C2 S1 126.32(13) . . ?
C3 C2 S1 126.71(13) . . ?
C4 C3 C8 119.51(15) . . ?
C4 C3 C2 134.07(16) . . ?
C8 C3 C2 106.36(15) . . ?
C5 C4 C3 118.47(16) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
C4 C5 C6 120.98(16) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C7 C6 C5 121.88(15) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C6 C7 C8 116.97(16) . . ?
C6 C7 H7A 121.5 . . ?
C8 C7 H7A 121.5 . . ?
N1 C8 C7 130.52(16) . . ?
N1 C8 C3 107.29(15) . . ?
C7 C8 C3 122.18(16) . . ?
C14 C9 C10 119.55(15) . . ?
C14 C9 S1 123.31(13) . . ?
C10 C9 S1 117.13(13) . . ?
C11 C10 C9 120.20(16) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 119.16(15) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C13 C12 C11 121.61(14) . . ?
C13 C12 Cl1 119.65(13) . . ?
C11 C12 Cl1 118.73(13) . . ?
C12 C13 C14 118.87(16) . . ?
C12 C13 H13A 120.6 . . ?
C14 C13 H13A 120.6 . . ?
C9 C14 C13 120.59(16) . . ?
C9 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
N2 C15 C16 109.62(16) . . ?
N2 C15 H15A 125.2 . . ?
C16 C15 H15A 125.2 . . ?
C15 C16 C17 107.15(16) . . ?
C15 C16 S3 125.00(13) . . ?
C17 C16 S3 127.36(13) . . ?
C18 C17 C22 119.13(15) . . ?
C18 C17 C16 134.29(15) . . ?
C22 C17 C16 106.55(15) . . ?
C19 C18 C17 118.19(15) . . ?
C19 C18 H18A 120.9 . . ?
C17 C18 H18A 120.9 . . ?
C18 C19 C20 121.65(16) . . ?
C18 C19 H19A 119.2 . . ?
C20 C19 H19A 119.2 . . ?
C21 C20 C19 121.09(16) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C20 C21 C22 117.78(16) . . ?
C20 C21 H21A 121.1 . . ?
C22 C21 H21A 121.1 . . ?
N2 C22 C21 130.91(16) . . ?
N2 C22 C17 106.85(15) . . ?
C21 C22 C17 122.09(16) . . ?
C28 C23 C24 119.92(15) . . ?
C28 C23 S3 117.17(13) . . ?
C24 C23 S3 122.88(13) . . ?
C25 C24 C23 120.03(16) . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C26 C25 C24 118.94(16) . . ?
C26 C25 H25A 120.5 . . ?
C24 C25 H25A 120.5 . . ?
C27 C26 C25 121.81(16) . . ?
C27 C26 Cl2 118.92(14) . . ?
C25 C26 Cl2 119.27(14) . . ?
C26 C27 C28 119.03(16) . . ?
C26 C27 H27A 120.5 . . ?
C28 C27 H27A 120.5 . . ?
C23 C28 C27 120.25(16) . . ?
C23 C28 H28A 119.9 . . ?
C27 C28 H28A 119.9 . . ?
C1 N1 C8 109.39(15) . . ?
C1 N1 H1 125.3 . . ?
C8 N1 H1 125.3 . . ?
C15 N2 C22 109.83(15) . . ?
C15 N2 H2 125.1 . . ?
C22 N2 H2 125.1 . . ?
C2 S1 C9 102.65(8) . . ?
C16 S3 C23 103.95(8) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.60
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.039
