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

#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_201309150_twin1_hklf4
_audit_creation_date             2013-09-18
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H6 N2 O S'
_chemical_formula_sum            'C10 H6 N2 O S'
_chemical_formula_weight         202.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20S1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3001(8)
_cell_length_b                   3.9310(2)
_cell_length_c                   20.1304(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.043(8)
_cell_angle_gamma                90.00
_cell_volume                     890.74(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    917
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      70.2700
_cell_measurement_theta_min      4.3570
_exptl_absorpt_coefficient_mu    2.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2612
_diffrn_reflns_theta_full        72.63
_diffrn_reflns_theta_max         72.63
_diffrn_reflns_theta_min         4.33
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   29.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   15.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  111.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -44.00   30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega -109.00  -25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -37.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -90.00  -65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  111.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega -110.00  -73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  8 omega   87.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  163.0000   14.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   76.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 10 omega   48.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   77.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   60.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 13 omega   82.00  133.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 14 omega   53.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   43.00   85.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   40.00  153.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 113

#__ type_ start__ end____ width___ exp.time_
 18 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 19 omega   26.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
 20 omega   18.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
 21 omega   26.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  120.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0084648000
_diffrn_orient_matrix_UB_12      -0.0620804000
_diffrn_orient_matrix_UB_13      -0.0758493000
_diffrn_orient_matrix_UB_21      -0.1364056000
_diffrn_orient_matrix_UB_22      -0.0153264000
_diffrn_orient_matrix_UB_23      -0.0013669000
_diffrn_orient_matrix_UB_31      -0.0067196000
_diffrn_orient_matrix_UB_32      0.3865975000
_diffrn_orient_matrix_UB_33      -0.0122504000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.5565 1507 2511
2 0.4435 1499 2511

_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2107
_reflns_number_total             2612
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1507P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.1945
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.09756(14) 0.2156(4) 0.24581(6) 0.0491(4) Uani 0.662(3) 1 d P A 1
S1A S -0.0818(4) -0.0768(12) 0.3074(2) 0.0491(4) Uani 0.338(3) 1 d P A 2
O1 O 0.2723(2) -0.3260(7) 0.58147(11) 0.0709(7) Uani 1 1 d . . .
N1 N 0.1631(2) -0.3592(8) 0.54479(12) 0.0610(7) Uani 1 1 d . . .
N2 N 0.3528(2) -0.1563(9) 0.54663(13) 0.0651(8) Uani 1 1 d . . .
C1 C 0.0946(2) -0.1670(7) 0.43156(13) 0.0427(6) Uani 1 1 d . . .
H1 H 0.0175 -0.2506 0.4311 0.051 Uiso 1 1 calc R . .
C2 C 0.1761(3) -0.2071(8) 0.48802(13) 0.0453(6) Uani 1 1 d . . .
C3 C 0.2957(3) -0.0811(8) 0.48950(14) 0.0497(7) Uani 1 1 d . . .
C4 C 0.3336(2) 0.0930(8) 0.43241(15) 0.0508(7) Uani 1 1 d . . .
H4 H 0.4104 0.1772 0.4319 0.061 Uiso 1 1 calc R . .
C5 C 0.2527(2) 0.1290(7) 0.37945(13) 0.0469(7) Uani 1 1 d . . .
H5 H 0.2755 0.2436 0.3422 0.056 Uiso 1 1 calc R . .
C6 C 0.1320(2) -0.0013(6) 0.37730(12) 0.0391(6) Uani 1 1 d . A .
C7 C 0.0538(2) 0.0416(7) 0.31646(12) 0.0418(6) Uani 1 1 d D . .
C8 C -0.0742(10) -0.072(4) 0.3073(6) 0.089(4) Uani 0.662(3) 1 d PD A 1
H8 H -0.1176 -0.1681 0.3397 0.107 Uiso 0.662(3) 1 calc PR A 1
C8A C 0.1013(16) 0.212(5) 0.2610(7) 0.089(4) Uani 0.338(3) 1 d PD A 2
H8A H 0.1767 0.3041 0.2592 0.107 Uiso 0.338(3) 1 calc PR A 2
C9 C -0.0344(5) 0.1480(15) 0.2016(3) 0.0471(14) Uani 0.662(3) 1 d P A 1
H9 H -0.0501 0.2074 0.1570 0.056 Uiso 0.662(3) 1 calc PR A 1
C9A C -0.0997(19) 0.058(4) 0.2281(7) 0.0471(14) Uani 0.338(3) 1 d P A 2
H9A H -0.1706 0.0351 0.2013 0.056 Uiso 0.338(3) 1 calc PR A 2
C10 C -0.1166(8) -0.0046(18) 0.2388(4) 0.0553(18) Uani 0.662(3) 1 d P A 1
H10 H -0.1930 -0.0595 0.2212 0.066 Uiso 0.662(3) 1 calc PR A 1
C10A C 0.0000(12) 0.204(4) 0.2068(9) 0.0553(18) Uani 0.338(3) 1 d PD A 2
H10A H 0.0049 0.2883 0.1639 0.066 Uiso 0.338(3) 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0549(8) 0.0531(7) 0.0390(5) 0.0034(5) 0.0020(5) -0.0014(6)
S1A 0.0549(8) 0.0531(7) 0.0390(5) 0.0034(5) 0.0020(5) -0.0014(6)
O1 0.0609(13) 0.1022(19) 0.0472(11) 0.0100(12) -0.0091(10) -0.0006(14)
N1 0.0541(15) 0.0830(19) 0.0448(12) 0.0087(12) -0.0026(11) 0.0011(14)
N2 0.0479(14) 0.092(2) 0.0532(14) -0.0031(14) -0.0083(12) -0.0045(15)
C1 0.0355(12) 0.0468(15) 0.0456(13) 0.0009(11) 0.0022(10) -0.0017(11)
C2 0.0431(14) 0.0515(15) 0.0412(12) -0.0043(11) 0.0034(11) 0.0010(12)
C3 0.0402(14) 0.0601(18) 0.0477(14) -0.0086(12) -0.0022(12) -0.0020(13)
C4 0.0314(12) 0.0642(19) 0.0567(16) -0.0062(13) 0.0039(12) -0.0071(13)
C5 0.0432(15) 0.0529(16) 0.0453(14) -0.0040(11) 0.0080(12) -0.0042(13)
C6 0.0360(13) 0.0364(12) 0.0446(12) -0.0048(10) 0.0014(10) 0.0026(11)
C7 0.0464(14) 0.0398(13) 0.0392(12) -0.0039(10) 0.0041(11) 0.0021(11)
C8 0.066(5) 0.108(7) 0.084(5) -0.036(4) -0.043(4) 0.018(4)
C8A 0.066(5) 0.108(7) 0.084(5) -0.036(4) -0.043(4) 0.018(4)
C9 0.054(4) 0.050(3) 0.036(2) -0.0017(18) -0.008(2) -0.009(3)
C9A 0.054(4) 0.050(3) 0.036(2) -0.0017(18) -0.008(2) -0.009(3)
C10 0.047(3) 0.051(3) 0.066(4) 0.002(2) 0.000(2) -0.003(3)
C10A 0.047(3) 0.051(3) 0.066(4) 0.002(2) 0.000(2) -0.003(3)

_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 C7 1.691(3) . ?
S1 C9 1.689(5) . ?
S1A C7 1.596(5) . ?
S1A C9A 1.677(14) . ?
O1 N1 1.388(4) . ?
O1 N2 1.370(4) . ?
N1 C2 1.309(4) . ?
N2 C3 1.302(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.408(4) . ?
C1 C6 1.370(4) . ?
C2 C3 1.437(4) . ?
C3 C4 1.435(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.349(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.455(3) . ?
C6 C7 1.456(4) . ?
C7 C8 1.510(11) . ?
C7 C8A 1.444(16) . ?
C8 H8 0.9300 . ?
C8 C10 1.444(14) . ?
C8A H8A 0.9300 . ?
C8A C10A 1.512(14) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(7) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.368(17) . ?
C10 H10 0.9300 . ?
C10A H10A 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
C9 S1 C7 94.0(3) . . ?
C7 S1A C9A 92.9(7) . . ?
N2 O1 N1 111.9(2) . . ?
C2 N1 O1 105.0(3) . . ?
C3 N2 O1 105.3(2) . . ?
C2 C1 H1 120.9 . . ?
C6 C1 H1 120.9 . . ?
C6 C1 C2 118.1(2) . . ?
N1 C2 C1 129.8(3) . . ?
N1 C2 C3 108.5(3) . . ?
C1 C2 C3 121.7(3) . . ?
N2 C3 C2 109.4(3) . . ?
N2 C3 C4 131.0(3) . . ?
C4 C3 C2 119.6(2) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 C3 117.0(2) . . ?
C5 C4 H4 121.5 . . ?
C4 C5 H5 118.2 . . ?
C4 C5 C6 123.7(3) . . ?
C6 C5 H5 118.2 . . ?
C1 C6 C5 119.9(2) . . ?
C1 C6 C7 121.3(2) . . ?
C5 C6 C7 118.8(2) . . ?
S1A C7 S1 111.8(2) . . ?
C6 C7 S1 123.6(2) . . ?
C6 C7 S1A 124.6(2) . . ?
C6 C7 C8 124.9(5) . . ?
C8 C7 S1 111.4(5) . . ?
C8 C7 S1A 0.6(7) . . ?
C8A C7 S1 6.6(7) . . ?
C8A C7 S1A 117.7(7) . . ?
C8A C7 C6 117.7(7) . . ?
C8A C7 C8 117.4(9) . . ?
C7 C8 H8 126.4 . . ?
C10 C8 C7 107.2(9) . . ?
C10 C8 H8 126.4 . . ?
C7 C8A H8A 128.1 . . ?
C7 C8A C10A 103.9(13) . . ?
C10A C8A H8A 128.1 . . ?
S1 C9 H9 123.6 . . ?
C10 C9 S1 112.8(5) . . ?
C10 C9 H9 123.6 . . ?
S1A C9A H9A 123.3 . . ?
C10A C9A S1A 113.4(14) . . ?
C10A C9A H9A 123.3 . . ?
C8 C10 H10 122.7 . . ?
C9 C10 C8 114.5(8) . . ?
C9 C10 H10 122.7 . . ?
C8A C10A H10A 124.0 . . ?
C9A C10A C8A 112.0(16) . . ?
C9A C10A H10A 124.0 . . ?

_database_code_depnum_ccdc_archive 'CCDC 965688'
