# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_mx1661
_database_code_depnum_ccdc_archive 'CCDC 882020'
_audit_update_record             
;
2012-05-14 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;
#TrackingRef 'mx1661.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Cl N3 S'
_chemical_formula_sum            'C14 H8 Cl N3 S'
_chemical_formula_weight         285.74

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           orthorhombic
_symmetry_space_group_name_H-M   Pccn

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

_cell_length_a                   7.4354(15)
_cell_length_b                   15.648(3)
_cell_length_c                   21.424(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2492.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8788
_cell_measurement_theta_min      1.30
_cell_measurement_theta_max      27.48

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8858
_exptl_absorpt_correction_T_max  0.9468
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19056
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2854
_reflns_number_gt                2817
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 Ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'

_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)+(0.0295P)²+1.6457P] 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_number_reflns         2854
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.220
_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
Cl1 Cl 0.62680(7) 1.15349(4) -0.19452(3) 0.04296(16) Uani 1 1 d . . .
S1 S 0.02542(7) 0.79725(3) 0.04768(2) 0.03643(15) Uani 1 1 d . . .
N1 N 0.12853(19) 0.89618(9) -0.04290(7) 0.0232(3) Uani 1 1 d . . .
N2 N 0.2551(2) 1.00945(10) -0.00152(7) 0.0289(3) Uani 1 1 d . . .
N3 N 0.2015(2) 0.95673(11) 0.04755(7) 0.0321(4) Uani 1 1 d . . .
C1 C 0.0029(2) 0.76281(12) -0.03031(10) 0.0319(4) Uani 1 1 d . . .
C2 C 0.0634(2) 0.82299(11) -0.07400(9) 0.0251(4) Uani 1 1 d . . .
C3 C 0.0596(2) 0.80613(11) -0.13720(9) 0.0284(4) Uani 1 1 d . . .
H3 H 0.1014 0.8470 -0.1666 0.034 Uiso 1 1 calc R . .
C4 C -0.0075(2) 0.72738(12) -0.15647(11) 0.0359(5) Uani 1 1 d . . .
H4 H -0.0114 0.7141 -0.1997 0.043 Uiso 1 1 calc R . .
C5 C -0.0688(3) 0.66783(12) -0.11323(13) 0.0418(5) Uani 1 1 d . . .
H5 H -0.1148 0.6147 -0.1275 0.050 Uiso 1 1 calc R . .
C6 C -0.0641(3) 0.68447(12) -0.05007(12) 0.0394(5) Uani 1 1 d . . .
H6 H -0.1057 0.6434 -0.0208 0.047 Uiso 1 1 calc R . .
C7 C 0.1266(2) 0.89049(12) 0.02082(9) 0.0277(4) Uani 1 1 d . . .
C8 C 0.2109(2) 0.97352(11) -0.05475(8) 0.0238(4) Uani 1 1 d . . .
C9 C 0.2382(2) 1.01444(10) -0.11564(8) 0.0240(3) Uani 1 1 d . . .
C10 C 0.4013(2) 1.05618(11) -0.12657(9) 0.0264(4) Uani 1 1 d . . .
H10 H 0.4955 1.0537 -0.0967 0.032 Uiso 1 1 calc R . .
C11 C 0.4232(2) 1.10113(12) -0.18155(9) 0.0287(4) Uani 1 1 d . . .
C12 C 0.2892(3) 1.10546(12) -0.22624(9) 0.0318(4) Uani 1 1 d . . .
H12 H 0.3073 1.1364 -0.2639 0.038 Uiso 1 1 calc R . .
C13 C 0.1275(3) 1.06353(12) -0.21492(9) 0.0313(4) Uani 1 1 d . . .
H13 H 0.0343 1.0657 -0.2452 0.038 Uiso 1 1 calc R . .
C14 C 0.1011(2) 1.01873(11) -0.15992(9) 0.0268(4) Uani 1 1 d . . .
H14 H -0.0104 0.9909 -0.1524 0.032 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
Cl1 C11 1.7435(18) . ?
S1 C7 1.7396(19) . ?
S1 C1 1.764(2) . ?
N1 C7 1.368(2) . ?
N1 C8 1.380(2) . ?
N1 C2 1.411(2) . ?
N2 C8 1.313(2) . ?
N2 N3 1.395(2) . ?
N3 C7 1.308(2) . ?
C1 C6 1.389(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.467(2) . ?
C9 C14 1.394(2) . ?
C9 C10 1.397(2) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 H14 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
C7 S1 C1 89.08(9) . . ?
C7 N1 C8 104.19(15) . . ?
C7 N1 C2 114.52(15) . . ?
C8 N1 C2 141.03(16) . . ?
C8 N2 N3 109.25(14) . . ?
C7 N3 N2 105.09(15) . . ?
C6 C1 C2 120.3(2) . . ?
C6 C1 S1 126.33(16) . . ?
C2 C1 S1 113.38(15) . . ?
C3 C2 C1 121.34(17) . . ?
C3 C2 N1 128.74(16) . . ?
C1 C2 N1 109.89(17) . . ?
C2 C3 C4 117.88(18) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 121.25(19) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 118.36(19) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
N3 C7 N1 112.39(16) . . ?
N3 C7 S1 134.72(15) . . ?
N1 C7 S1 112.90(14) . . ?
N2 C8 N1 109.08(15) . . ?
N2 C8 C9 123.40(15) . . ?
N1 C8 C9 127.42(15) . . ?
C14 C9 C10 119.87(16) . . ?
C14 C9 C8 121.66(16) . . ?
C10 C9 C8 118.23(16) . . ?
C11 C10 C9 118.91(17) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 122.00(17) . . ?
C10 C11 Cl1 118.53(14) . . ?
C12 C11 Cl1 119.46(14) . . ?
C11 C12 C13 118.60(17) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 120.63(17) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 119.98(17) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?

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
C8 N2 N3 C7 0.1(2) . . . . ?
C7 S1 C1 C6 176.31(17) . . . . ?
C7 S1 C1 C2 -2.76(14) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
S1 C1 C2 C3 178.59(14) . . . . ?
C6 C1 C2 N1 -178.70(16) . . . . ?
S1 C1 C2 N1 0.43(18) . . . . ?
C7 N1 C2 C3 -174.92(17) . . . . ?
C8 N1 C2 C3 -2.1(3) . . . . ?
C7 N1 C2 C1 3.1(2) . . . . ?
C8 N1 C2 C1 175.9(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
N1 C2 C3 C4 178.19(16) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
S1 C1 C6 C5 -178.83(15) . . . . ?
N2 N3 C7 N1 0.3(2) . . . . ?
N2 N3 C7 S1 -179.60(15) . . . . ?
C8 N1 C7 N3 -0.6(2) . . . . ?
C2 N1 C7 N3 174.79(15) . . . . ?
C8 N1 C7 S1 179.35(11) . . . . ?
C2 N1 C7 S1 -5.28(19) . . . . ?
C1 S1 C7 N3 -175.6(2) . . . . ?
C1 S1 C7 N1 4.49(14) . . . . ?
N3 N2 C8 N1 -0.47(19) . . . . ?
N3 N2 C8 C9 176.20(16) . . . . ?
C7 N1 C8 N2 0.63(19) . . . . ?
C2 N1 C8 N2 -172.67(19) . . . . ?
C7 N1 C8 C9 -175.87(17) . . . . ?
C2 N1 C8 C9 10.8(3) . . . . ?
N2 C8 C9 C14 -130.81(19) . . . . ?
N1 C8 C9 C14 45.2(3) . . . . ?
N2 C8 C9 C10 43.6(2) . . . . ?
N1 C8 C9 C10 -140.33(17) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
C8 C9 C10 C11 -174.59(16) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 Cl1 179.64(13) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
Cl1 C11 C12 C13 -179.75(15) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C8 C9 C14 C13 175.06(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.047


