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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 Cl N3 O2 S'
_chemical_formula_weight         359.82

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'
Cl Cl 0.1484 0.1585 '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                   9.774(2)
_cell_length_b                   9.830(2)
_cell_length_c                   9.908(2)
_cell_angle_alpha                91.70(3)
_cell_angle_beta                 110.52(3)
_cell_angle_gamma                106.41(3)
_cell_volume                     846.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.8988
_exptl_absorpt_correction_T_max  0.9646
_exptl_absorpt_process_details   '(North, Phillips & Mathews,1968)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3311
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.37
_reflns_number_total             3113
_reflns_number_gt                2102
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0600P)²+1.1000P] 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         3113
_refine_ls_number_parameters     217
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1710
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.016
_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
Cl Cl 1.09950(10) 0.33123(8) 0.27740(9) 0.0433(3) Uani 1 1 d U . .
S S 0.5891(3) 0.0933(3) 0.8850(2) 0.1427(8) Uani 1 1 d . . .
O1 O 0.7834(4) 0.0937(4) 0.5975(4) 0.0926(10) Uani 1 1 d . . .
N1 N 0.6410(6) -0.1292(5) 0.5099(6) 0.1012(14) Uani 1 1 d . . .
C1 C 0.6521(10) 0.2399(10) 0.9905(7) 0.139(3) Uani 1 1 d U . .
H1B H 0.6205 0.2577 1.0656 0.167 Uiso 1 1 calc R . .
O2 O 0.8732(5) -0.3690(5) 0.2837(5) 0.1222(15) Uani 1 1 d . . .
N2 N 0.6143(6) -0.0794(5) 0.6333(6) 0.1066(15) Uani 1 1 d . . .
C2 C 0.7714(10) 0.3461(9) 0.9503(8) 0.136(3) Uani 1 1 d U . .
H2B H 0.8188 0.4398 0.9979 0.163 Uiso 1 1 calc R . .
C3 C 0.8049(6) 0.2983(6) 0.8433(6) 0.0879(15) Uani 1 1 d . . .
H3A H 0.8760 0.3499 0.8062 0.106 Uiso 1 1 calc R . .
N3 N 0.6997(5) -0.2585(5) 0.2947(5) 0.0991(14) Uani 1 1 d . . .
H3C H 0.6106 -0.2714 0.2989 0.119 Uiso 1 1 calc R . .
C4 C 0.7053(7) 0.1438(7) 0.7929(6) 0.0964(16) Uani 1 1 d . . .
C5 C 0.6953(6) 0.0467(6) 0.6767(6) 0.0861(15) Uani 1 1 d . . .
C6 C 0.7434(6) -0.0214(6) 0.4983(6) 0.0872(15) Uani 1 1 d . . .
C7 C 0.8132(6) -0.0037(6) 0.3874(6) 0.0836(14) Uani 1 1 d . . .
C8 C 0.9065(7) 0.1278(6) 0.3875(6) 0.0926(16) Uani 1 1 d . . .
H8A H 0.9314 0.2030 0.4599 0.111 Uiso 1 1 calc R . .
C9 C 0.9649(6) 0.1482(5) 0.2764(7) 0.0899(16) Uani 1 1 d U . .
C10 C 0.9269(6) 0.0404(6) 0.1686(6) 0.0935(16) Uani 1 1 d . . .
H10A H 0.9635 0.0578 0.0938 0.112 Uiso 1 1 calc R . .
C11 C 0.8344(7) -0.0953(7) 0.1685(6) 0.0970(17) Uani 1 1 d . . .
C12 C 0.7821(7) -0.1205(6) 0.2822(6) 0.0933(16) Uani 1 1 d . . .
C13 C 0.7803(9) -0.2099(7) 0.0368(7) 0.128(2) Uani 1 1 d . . .
H13A H 0.7173 -0.2976 0.0524 0.192 Uiso 1 1 calc R . .
H13B H 0.8680 -0.2255 0.0243 0.192 Uiso 1 1 calc R . .
H13C H 0.7216 -0.1783 -0.0489 0.192 Uiso 1 1 calc R . .
C14 C 0.7534(8) -0.3753(7) 0.3008(7) 0.0991(17) Uani 1 1 d . . .
C15 C 0.6582(8) -0.5094(7) 0.3277(7) 0.1029(18) Uani 1 1 d . . .
C16 C 0.4932(9) -0.5305(8) 0.2911(10) 0.159(3) Uani 1 1 d . . .
H16A H 0.4468 -0.6204 0.3169 0.238 Uiso 1 1 calc R . .
H16B H 0.4441 -0.5305 0.1885 0.238 Uiso 1 1 calc R . .
H16C H 0.4812 -0.4542 0.3441 0.238 Uiso 1 1 calc R . .
C17 C 0.7208(10) -0.6152(8) 0.3676(11) 0.162(3) Uani 1 1 d . . .
H17C H 0.6593 -0.7049 0.3726 0.194 Uiso 1 1 calc R . .
H17A H 0.8254 -0.5984 0.3900 0.194 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
Cl C9 1.902(4) . ?
S C1 1.583(8) . ?
S C4 1.674(6) . ?
O1 C6 1.346(6) . ?
O1 C5 1.357(6) . ?
N1 C6 1.275(6) . ?
N1 N2 1.437(6) . ?
C1 C2 1.507(11) . ?
C1 H1B 0.9300 . ?
O2 C14 1.225(7) . ?
N2 C5 1.235(6) . ?
C2 C3 1.324(8) . ?
C2 H2B 0.9300 . ?
C3 C4 1.511(8) . ?
C3 H3A 0.9300 . ?
N3 C14 1.386(7) . ?
N3 C12 1.402(6) . ?
N3 H3C 0.8600 . ?
C4 C5 1.431(8) . ?
C6 C7 1.475(7) . ?
C7 C8 1.354(7) . ?
C7 C12 1.417(7) . ?
C8 C9 1.403(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.354(7) . ?
C10 C11 1.384(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.394(7) . ?
C11 C13 1.531(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.476(8) . ?
C15 C17 1.352(9) . ?
C15 C16 1.474(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17C 0.9300 . ?
C17 H17A 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
C1 S C4 96.1(4) . . ?
C6 O1 C5 103.1(4) . . ?
C6 N1 N2 103.2(5) . . ?
C2 C1 S 109.4(5) . . ?
C2 C1 H1B 125.3 . . ?
S C1 H1B 125.3 . . ?
C5 N2 N1 108.3(5) . . ?
C3 C2 C1 116.1(7) . . ?
C3 C2 H2B 121.9 . . ?
C1 C2 H2B 121.9 . . ?
C2 C3 C4 106.7(6) . . ?
C2 C3 H3A 126.6 . . ?
C4 C3 H3A 126.6 . . ?
C14 N3 C12 123.9(5) . . ?
C14 N3 H3C 118.1 . . ?
C12 N3 H3C 118.1 . . ?
C5 C4 C3 128.2(5) . . ?
C5 C4 S 120.1(5) . . ?
C3 C4 S 111.5(4) . . ?
N2 C5 O1 111.8(5) . . ?
N2 C5 C4 129.3(6) . . ?
O1 C5 C4 118.9(5) . . ?
N1 C6 O1 113.5(5) . . ?
N1 C6 C7 129.2(5) . . ?
O1 C6 C7 117.1(5) . . ?
C8 C7 C12 120.8(5) . . ?
C8 C7 C6 118.3(5) . . ?
C12 C7 C6 120.9(5) . . ?
C7 C8 C9 118.7(5) . . ?
C7 C8 H8A 120.6 . . ?
C9 C8 H8A 120.6 . . ?
C10 C9 C8 121.2(5) . . ?
C10 C9 Cl 119.6(4) . . ?
C8 C9 Cl 119.2(4) . . ?
C9 C10 C11 120.8(5) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C10 C11 C12 119.1(5) . . ?
C10 C11 C13 119.1(6) . . ?
C12 C11 C13 121.6(6) . . ?
C11 C12 N3 121.6(5) . . ?
C11 C12 C7 119.0(5) . . ?
N3 C12 C7 119.5(5) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 N3 122.2(6) . . ?
O2 C14 C15 121.2(6) . . ?
N3 C14 C15 116.6(6) . . ?
C17 C15 C16 122.2(7) . . ?
C17 C15 C14 118.7(7) . . ?
C16 C15 C14 118.6(6) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17C 120.0 . . ?
C15 C17 H17A 120.0 . . ?
H17C C17 H17A 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
C4 S C1 C2 3.0(6) . . . . ?
C6 N1 N2 C5 1.9(7) . . . . ?
S C1 C2 C3 -2.5(8) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C5 177.8(6) . . . . ?
C2 C3 C4 S 1.7(6) . . . . ?
C1 S C4 C5 -179.3(5) . . . . ?
C1 S C4 C3 -2.9(5) . . . . ?
N1 N2 C5 O1 -1.5(7) . . . . ?
N1 N2 C5 C4 177.7(5) . . . . ?
C6 O1 C5 N2 0.6(6) . . . . ?
C6 O1 C5 C4 -178.8(5) . . . . ?
C3 C4 C5 N2 -179.5(6) . . . . ?
S C4 C5 N2 -3.7(9) . . . . ?
C3 C4 C5 O1 -0.3(9) . . . . ?
S C4 C5 O1 175.5(4) . . . . ?
N2 N1 C6 O1 -1.6(6) . . . . ?
N2 N1 C6 C7 -176.8(5) . . . . ?
C5 O1 C6 N1 0.7(6) . . . . ?
C5 O1 C6 C7 176.6(5) . . . . ?
N1 C6 C7 C8 171.9(6) . . . . ?
O1 C6 C7 C8 -3.2(7) . . . . ?
N1 C6 C7 C12 -7.3(9) . . . . ?
O1 C6 C7 C12 177.6(5) . . . . ?
C12 C7 C8 C9 3.6(8) . . . . ?
C6 C7 C8 C9 -175.6(5) . . . . ?
C7 C8 C9 C10 1.4(9) . . . . ?
C7 C8 C9 Cl -178.7(4) . . . . ?
C8 C9 C10 C11 -2.8(9) . . . . ?
Cl C9 C10 C11 177.3(4) . . . . ?
C9 C10 C11 C12 -0.9(9) . . . . ?
C9 C10 C11 C13 173.6(6) . . . . ?
C10 C11 C12 N3 -174.2(5) . . . . ?
C13 C11 C12 N3 11.4(9) . . . . ?
C10 C11 C12 C7 5.8(9) . . . . ?
C13 C11 C12 C7 -168.6(6) . . . . ?
C14 N3 C12 C11 55.9(8) . . . . ?
C14 N3 C12 C7 -124.1(6) . . . . ?
C8 C7 C12 C11 -7.3(8) . . . . ?
C6 C7 C12 C11 171.9(5) . . . . ?
C8 C7 C12 N3 172.7(5) . . . . ?
C6 C7 C12 N3 -8.1(8) . . . . ?
C12 N3 C14 O2 -6.1(10) . . . . ?
C12 N3 C14 C15 174.5(5) . . . . ?
O2 C14 C15 C17 15.5(10) . . . . ?
N3 C14 C15 C17 -165.0(7) . . . . ?
O2 C14 C15 C16 -156.3(7) . . . . ?
N3 C14 C15 C16 23.1(9) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 990869'
