# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_fe118

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 N3 O S'
_chemical_formula_weight         255.29

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'

_symm_symmetry_cell_setting      monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'


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

_cell_length_a                   6.255(3)
_cell_length_b                   18.109(7)
_cell_length_c                   10.221(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.525(6)
_cell_angle_gamma                90.00
_cell_volume                     1152.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7736
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.56
_reflns_number_total             2638
_reflns_number_gt                1387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (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)+(0.0340P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2638
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_restrained_S_all      0.823
_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 0.82180(8) 0.02267(3) 0.63086(5) 0.05291(18) Uani 1 1 d . . .
O1 O 0.6532(2) 0.09519(7) 0.48704(13) 0.0628(4) Uani 1 1 d . . .
N1 N 0.9007(3) -0.03294(7) 0.76860(14) 0.0475(4) Uani 1 1 d . . .
N2 N 0.5737(2) 0.00827(8) 0.82170(14) 0.0478(4) Uani 1 1 d . . .
N3 N 0.4331(3) 0.08486(8) 0.65156(15) 0.0501(4) Uani 1 1 d . . .
C1 C 1.0869(3) -0.07149(11) 0.7881(2) 0.0602(6) Uani 1 1 d . . .
H1 H 1.1855 -0.0704 0.7256 0.072 Uiso 1 1 calc R . .
C2 C 1.1278(3) -0.11164(11) 0.8994(2) 0.0665(6) Uani 1 1 d . . .
H2 H 1.2544 -0.1386 0.9138 0.080 Uiso 1 1 calc R . .
C3 C 0.9783(3) -0.11222(11) 0.9924(2) 0.0630(6) Uani 1 1 d . . .
H3 H 1.0066 -0.1394 1.0693 0.076 Uiso 1 1 calc R . .
C4 C 0.7921(3) -0.07362(10) 0.97189(19) 0.0568(6) Uani 1 1 d . . .
H4 H 0.6932 -0.0743 1.0342 0.068 Uiso 1 1 calc R . .
C5 C 0.7507(3) -0.03283(10) 0.85611(18) 0.0470(5) Uani 1 1 d . . .
C6 C 0.5866(3) 0.04044(10) 0.70783(19) 0.0471(5) Uani 1 1 d . . .
C7 C 0.4821(3) 0.11207(10) 0.53647(19) 0.0496(5) Uani 1 1 d . . .
C8 C 0.3292(3) 0.16465(10) 0.46730(18) 0.0493(5) Uani 1 1 d . . .
C9 C 0.1392(3) 0.18316(10) 0.51729(19) 0.0572(6) Uani 1 1 d . . .
H9 H 0.1059 0.1619 0.5956 0.069 Uiso 1 1 calc R . .
C10 C -0.0018(3) 0.23240(8) 0.45360(16) 0.0675(6) Uani 1 1 d . . .
H10 H -0.1301 0.2436 0.4882 0.081 Uiso 1 1 calc R . .
C11 C 0.0463(3) 0.26506(8) 0.33924(16) 0.0701(6) Uani 1 1 d R . .
H11 H -0.0474 0.2992 0.2969 0.084 Uiso 1 1 calc R . .
C12 C 0.2335(4) 0.24700(12) 0.2877(2) 0.0741(7) Uani 1 1 d . . .
H12 H 0.2652 0.2686 0.2093 0.089 Uiso 1 1 calc R . .
C13 C 0.3758(4) 0.19726(11) 0.3501(2) 0.0642(6) Uani 1 1 d . . .
H13 H 0.5024 0.1856 0.3140 0.077 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 N1 1.7623(16) . ?
S1 C6 1.7638(19) . ?
S1 O1 2.1679(15) . ?
O1 C7 1.264(2) . ?
N1 C1 1.356(2) . ?
N1 C5 1.357(2) . ?
N2 C6 1.311(2) . ?
N2 C5 1.352(2) . ?
N3 C7 1.338(2) . ?
N3 C6 1.339(2) . ?
C1 C2 1.354(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.357(3) . ?
C4 C5 1.398(3) . ?
C7 C8 1.480(3) . ?
C8 C9 1.380(3) . ?
C8 C13 1.391(2) . ?
C9 C10 1.373(2) . ?
C10 C11 1.3689 . ?
C11 C12 1.369(3) . ?
C12 C13 1.379(3) . ?

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
N1 S1 C6 85.96(9) . . ?
N1 S1 O1 165.56(6) . . ?
C6 S1 O1 79.60(8) . . ?
C7 O1 S1 104.53(12) . . ?
C1 N1 C5 122.85(17) . . ?
C1 N1 S1 125.60(13) . . ?
C5 N1 S1 111.54(13) . . ?
C6 N2 C5 110.90(16) . . ?
C7 N3 C6 112.52(16) . . ?
C2 C1 N1 119.36(18) . . ?
C1 C2 C3 119.4(2) . . ?
C4 C3 C2 120.8(2) . . ?
C3 C4 C5 119.28(18) . . ?
N2 C5 N1 115.48(17) . . ?
N2 C5 C4 126.26(17) . . ?
N1 C5 C4 118.26(18) . . ?
N2 C6 N3 123.05(17) . . ?
N2 C6 S1 116.11(15) . . ?
N3 C6 S1 120.83(15) . . ?
O1 C7 N3 122.49(19) . . ?
O1 C7 C8 119.84(17) . . ?
N3 C7 C8 117.67(17) . . ?
C9 C8 C13 118.36(19) . . ?
C9 C8 C7 121.30(17) . . ?
C13 C8 C7 120.33(19) . . ?
C10 C9 C8 121.26(17) . . ?
C11 C10 C9 120.10(11) . . ?
C10 C11 C12 119.44(12) . . ?
C11 C12 C13 121.07(19) . . ?
C12 C13 C8 119.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 711636'
#######################################################################
#
#                 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_fe065

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N3 O S'
_chemical_formula_weight         269.32

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_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2ybn '


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

_cell_length_a                   11.678(6)
_cell_length_b                   3.995(2)
_cell_length_c                   26.939(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.965(9)
_cell_angle_gamma                90.00
_cell_volume                     1241.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .05


_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.1
_exptl_absorpt_correction_T_max  0.2
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2001)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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 CCD area-detector'
_diffrn_measurement_method       ω/2θ

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5715
_diffrn_reflns_av_R_equivalents  0.1544
_diffrn_reflns_av_unetI/net      0.1327
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         23.94
_reflns_number_total             1924
_reflns_number_gt                1286
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (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)+(0.0751P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1924
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1603
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.88240(6) 0.2335(2) 0.01924(4) 0.0453(4) Uani 1 1 d . . .
O1 O 0.98631(18) 0.0268(6) 0.08528(9) 0.0545(7) Uani 1 1 d . . .
N1 N 0.7682(2) 0.3634(6) -0.02773(11) 0.0414(7) Uani 1 1 d . . .
N2 N 0.6645(2) 0.1062(7) 0.02668(11) 0.0445(7) Uani 1 1 d . . .
N3 N 0.7994(2) -0.0829(7) 0.09504(11) 0.0452(8) Uani 1 1 d . . .
C1 C 0.7784(3) 0.5343(9) -0.07106(14) 0.0500(9) Uani 1 1 d . . .
H1 H 0.8513 0.5954 -0.0778 0.060 Uiso 1 1 calc R . .
C2 C 0.6830(3) 0.6140(9) -0.10389(15) 0.0515(10) Uani 1 1 d . . .
H2 H 0.6905 0.7302 -0.1331 0.062 Uiso 1 1 calc R . .
C3 C 0.5703(3) 0.5213(8) -0.09416(14) 0.0451(9) Uani 1 1 d . . .
C4 C 0.5625(3) 0.3498(8) -0.05124(14) 0.0438(9) Uani 1 1 d . . .
H4 H 0.4902 0.2844 -0.0444 0.053 Uiso 1 1 calc R . .
C5 C 0.6619(3) 0.2704(7) -0.01711(14) 0.0393(8) Uani 1 1 d . . .
C6 C 0.7723(3) 0.0673(8) 0.05095(14) 0.0414(9) Uani 1 1 d . . .
C7 C 0.9144(3) -0.0956(8) 0.11096(14) 0.0447(9) Uani 1 1 d . . .
C8 C 0.9558(3) -0.2566(8) 0.16002(14) 0.0462(9) Uani 1 1 d . . .
C9 C 1.0745(3) -0.2780(9) 0.17740(16) 0.0560(11) Uani 1 1 d . . .
H9 H 1.1271 -0.1902 0.1583 0.067 Uiso 1 1 calc R . .
C10 C 1.1140(3) -0.4285(10) 0.22272(18) 0.0686(13) Uani 1 1 d . . .
H10 H 1.1932 -0.4409 0.2341 0.082 Uiso 1 1 calc R . .
C11 C 1.0375(4) -0.5608(10) 0.25145(17) 0.0716(13) Uani 1 1 d . . .
H11 H 1.0649 -0.6630 0.2820 0.086 Uiso 1 1 calc R . .
C12 C 0.9194(4) -0.5407(11) 0.23451(17) 0.0710(12) Uani 1 1 d . . .
H12 H 0.8671 -0.6271 0.2539 0.085 Uiso 1 1 calc R . .
C13 C 0.8799(3) -0.3936(10) 0.18917(15) 0.0602(11) Uani 1 1 d . . .
H13 H 0.8006 -0.3856 0.1777 0.072 Uiso 1 1 calc R . .
C14 C 0.4636(3) 0.6132(9) -0.13051(15) 0.0582(10) Uani 1 1 d . . .
H14A H 0.3995 0.4784 -0.1240 0.087 Uiso 1 1 calc R . .
H14B H 0.4773 0.5745 -0.1643 0.087 Uiso 1 1 calc R . .
H14C H 0.4458 0.8453 -0.1265 0.087 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 N1 1.767(3) . ?
S1 C6 1.780(3) . ?
S1 O1 2.156(3) . ?
O1 C7 1.266(4) . ?
N1 C5 1.368(4) . ?
N1 C1 1.373(5) . ?
N2 C6 1.333(4) . ?
N2 C5 1.346(5) . ?
N3 C6 1.324(5) . ?
N3 C7 1.346(4) . ?
C1 C2 1.348(5) . ?
C2 C3 1.430(5) . ?
C3 C4 1.359(5) . ?
C3 C14 1.506(4) . ?
C4 C5 1.400(4) . ?
C7 C8 1.481(5) . ?
C8 C13 1.385(5) . ?
C8 C9 1.395(5) . ?
C9 C10 1.374(6) . ?
C10 C11 1.375(6) . ?
C11 C12 1.386(6) . ?
C12 C13 1.369(6) . ?

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
N1 S1 C6 86.10(15) . . ?
N1 S1 O1 165.54(11) . . ?
C6 S1 O1 79.44(14) . . ?
C7 O1 S1 105.24(19) . . ?
C5 N1 C1 120.9(3) . . ?
C5 N1 S1 112.3(3) . . ?
C1 N1 S1 126.8(2) . . ?
C6 N2 C5 112.2(3) . . ?
C6 N3 C7 113.0(3) . . ?
C2 C1 N1 120.2(3) . . ?
C1 C2 C3 120.6(4) . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 C14 121.2(3) . . ?
C2 C3 C14 120.7(3) . . ?
C3 C4 C5 121.0(3) . . ?
N2 C5 N1 114.7(3) . . ?
N2 C5 C4 126.1(3) . . ?
N1 C5 C4 119.2(3) . . ?
N3 C6 N2 124.6(3) . . ?
N3 C6 S1 120.7(2) . . ?
N2 C6 S1 114.7(3) . . ?
O1 C7 N3 121.7(3) . . ?
O1 C7 C8 120.2(3) . . ?
N3 C7 C8 118.1(3) . . ?
C13 C8 C9 118.4(4) . . ?
C13 C8 C7 121.9(3) . . ?
C9 C8 C7 119.7(4) . . ?
C10 C9 C8 120.2(4) . . ?
C9 C10 C11 120.7(4) . . ?
C10 C11 C12 119.5(4) . . ?
C13 C12 C11 119.9(4) . . ?
C12 C13 C8 121.3(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        23.94
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.260
_database_code_depnum_ccdc_archive 'CCDC 713327'
#######################################################################
#
#                 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_C2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Cl2 Cu N6 O2 S2'
_chemical_formula_sum            'C28 H22 Cl2 Cu N6 O2 S2'
_chemical_formula_weight         673.08

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
_symmetry_space_group_name_Hall  '-P 1 '

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

_cell_length_a                   8.158(5)
_cell_length_b                   8.426(5)
_cell_length_c                   11.183(6)
_cell_angle_alpha                78.716(8)
_cell_angle_beta                 76.857(8)
_cell_angle_gamma                71.514(8)
_cell_volume                     703.6(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    35
_cell_measurement_theta_min      4
_cell_measurement_theta_max      23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             343
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;


_diffrn_ambient_temperature      294(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 CCD area-detector'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5539
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         29.49
_reflns_number_total             3840
_reflns_number_gt                2770
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (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)+(0.0499P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3840
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_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
Cu1 Cu 0.5000 0.5000 0.0000 0.03483(12) Uani 1 2 d S . .
Cl1 Cl 0.76632(8) 0.54168(7) -0.08041(6) 0.05141(17) Uani 1 1 d . . .
S1 S 0.30605(7) 1.01025(6) 0.13118(6) 0.04097(15) Uani 1 1 d . . .
O1 O 0.4145(2) 0.9315(2) 0.29603(16) 0.0540(4) Uani 1 1 d . . .
N1 N 0.2380(2) 1.0203(2) -0.01259(17) 0.0370(4) Uani 1 1 d . . .
N2 N 0.3939(2) 0.7439(2) 0.01640(17) 0.0372(4) Uani 1 1 d . . .
N3 N 0.5007(3) 0.6952(2) 0.20132(18) 0.0417(4) Uani 1 1 d . . .
C1 C 0.1348(3) 1.1597(3) -0.0725(2) 0.0442(6) Uani 1 1 d . . .
H1 H 0.0946 1.2614 -0.0399 0.053 Uiso 1 1 calc R . .
C2 C 0.0915(3) 1.1488(3) -0.1795(2) 0.0474(6) Uani 1 1 d . . .
H2 H 0.0213 1.2440 -0.2204 0.057 Uiso 1 1 calc R . .
C3 C 0.1508(3) 0.9954(3) -0.2305(2) 0.0451(5) Uani 1 1 d . . .
C4 C 0.2525(3) 0.8557(3) -0.1673(2) 0.0433(5) Uani 1 1 d . . .
H4 H 0.2922 0.7527 -0.1981 0.052 Uiso 1 1 calc R . .
C5 C 0.2956(3) 0.8691(2) -0.0570(2) 0.0367(5) Uani 1 1 d . . .
C6 C 0.4104(3) 0.7963(2) 0.1169(2) 0.0372(5) Uani 1 1 d . . .
C7 C 0.4975(3) 0.7773(3) 0.2939(2) 0.0430(5) Uani 1 1 d . . .
C8 C 0.5953(3) 0.6841(3) 0.3949(2) 0.0439(5) Uani 1 1 d . . .
C9 C 0.7132(4) 0.5261(3) 0.3842(3) 0.0595(7) Uani 1 1 d . . .
H9 H 0.7323 0.4763 0.3132 0.071 Uiso 1 1 calc R . .
C10 C 0.8027(4) 0.4429(4) 0.4801(3) 0.0751(9) Uani 1 1 d . . .
H10 H 0.8828 0.3369 0.4733 0.090 Uiso 1 1 calc R . .
C11 C 0.7736(5) 0.5164(4) 0.5855(3) 0.0730(9) Uani 1 1 d . . .
H11 H 0.8327 0.4585 0.6502 0.088 Uiso 1 1 calc R . .
C12 C 0.6602(4) 0.6718(4) 0.5962(3) 0.0684(8) Uani 1 1 d . . .
H12 H 0.6427 0.7211 0.6672 0.082 Uiso 1 1 calc R . .
C13 C 0.5704(4) 0.7569(4) 0.5012(2) 0.0577(7) Uani 1 1 d . . .
H13 H 0.4926 0.8639 0.5084 0.069 Uiso 1 1 calc R . .
C14 C 0.1025(4) 0.9882(4) -0.3508(2) 0.0616(7) Uani 1 1 d . . .
H14A H 0.1562 0.8769 -0.3739 0.092 Uiso 1 1 calc R . .
H14B H 0.1433 1.0688 -0.4142 0.092 Uiso 1 1 calc R . .
H14C H -0.0228 1.0143 -0.3412 0.092 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
Cu1 N2 1.988(2) . ?
Cu1 N2 1.988(2) 2_665 ?
Cu1 Cl1 2.2637(14) . ?
Cu1 Cl1 2.2637(14) 2_665 ?
S1 C6 1.754(2) . ?
S1 N1 1.795(2) . ?
S1 O1 2.124(2) . ?
O1 C7 1.262(3) . ?
N1 C5 1.361(3) . ?
N1 C1 1.364(3) . ?
N2 C6 1.333(3) . ?
N2 C5 1.362(3) . ?
N3 C6 1.328(3) . ?
N3 C7 1.345(3) . ?
C1 C2 1.349(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.413(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 C14 1.502(4) . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C7 C8 1.481(3) . ?
C8 C9 1.382(3) . ?
C8 C13 1.389(4) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.352(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
N2 Cu1 N2 180.0 . 2_665 ?
N2 Cu1 Cl1 91.10(6) . . ?
N2 Cu1 Cl1 88.90(6) 2_665 . ?
N2 Cu1 Cl1 88.90(6) . 2_665 ?
N2 Cu1 Cl1 91.10(6) 2_665 2_665 ?
Cl1 Cu1 Cl1 180.0 . 2_665 ?
C6 S1 N1 85.53(10) . . ?
C6 S1 O1 79.71(9) . . ?
N1 S1 O1 165.22(7) . . ?
C7 O1 S1 105.68(15) . . ?
C5 N1 C1 121.4(2) . . ?
C5 N1 S1 112.92(14) . . ?
C1 N1 S1 125.63(15) . . ?
C6 N2 C5 112.73(18) . . ?
C6 N2 Cu1 117.29(14) . . ?
C5 N2 Cu1 129.87(15) . . ?
C6 N3 C7 111.69(19) . . ?
C2 C1 N1 119.4(2) . . ?
C2 C1 H1 120.3 . . ?
N1 C1 H1 120.3 . . ?
C1 C2 C3 121.2(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 C14 121.8(2) . . ?
C2 C3 C14 119.9(2) . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 N2 113.1(2) . . ?
N1 C5 C4 119.90(19) . . ?
N2 C5 C4 127.03(19) . . ?
N3 C6 N2 122.93(19) . . ?
N3 C6 S1 121.32(17) . . ?
N2 C6 S1 115.75(16) . . ?
O1 C7 N3 121.6(2) . . ?
O1 C7 C8 119.6(2) . . ?
N3 C7 C8 118.8(2) . . ?
C9 C8 C13 119.3(2) . . ?
C9 C8 C7 120.9(2) . . ?
C13 C8 C7 119.7(2) . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        29.49
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.084
_database_code_depnum_ccdc_archive 'CCDC 714500'
#######################################################################
#
#                 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_C3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Cl2 Cu N6 O2 S2'
_chemical_formula_sum            'C28 H22 Cl2 Cu N6 O2 S2'
_chemical_formula_weight         673.08

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'
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'
Cu Cu 0.3201 1.2651 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc '

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

_cell_length_a                   13.947(4)
_cell_length_b                   14.750(5)
_cell_length_c                   13.897(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.561(5)
_cell_angle_gamma                90.00
_cell_volume                     2827.1(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    34
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      23.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .12
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1372
_exptl_absorpt_coefficient_mu    1.149
_exptl_absorpt_correction_type   Psi-Scans
_exptl_absorpt_correction_T_min  0.8
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2001)'

_exptl_special_details           
;  
;

_diffrn_ambient_temperature      294(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 CCD area-detector'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19159
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0802
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.25
_reflns_number_total             6968
_reflns_number_gt                3969
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (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)+(0.0407P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6968
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_restrained_S_all      0.846
_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
Cu1 Cu 0.77000(2) 0.03157(2) 0.37696(2) 0.03623(11) Uani 1 1 d . . .
Cl2 Cl 0.80418(7) -0.01640(5) 0.53232(6) 0.0635(3) Uani 1 1 d . . .
Cl1 Cl 0.75833(7) 0.08341(5) 0.22449(5) 0.0643(3) Uani 1 1 d . . .
S1 S 0.72001(6) 0.31609(5) 0.48078(5) 0.0448(2) Uani 1 1 d . . .
N1 N 0.61198(17) 0.24704(15) 0.47325(15) 0.0404(6) Uani 1 1 d . . .
N2 N 0.71838(17) 0.14692(15) 0.42300(15) 0.0387(5) Uani 1 1 d . . .
N3 N 0.86703(17) 0.22060(14) 0.42581(15) 0.0399(6) Uani 1 1 d . . .
O1 O 0.85739(14) 0.36768(13) 0.47430(14) 0.0521(5) Uani 1 1 d . . .
C1 C 0.5245(2) 0.2756(2) 0.4953(2) 0.0456(7) Uani 1 1 d . . .
C2 C 0.4504(2) 0.2145(2) 0.4853(2) 0.0527(8) Uani 1 1 d . . .
H2 H 0.3901 0.2317 0.5001 0.063 Uiso 1 1 calc R . .
C3 C 0.4636(2) 0.1270(2) 0.4535(2) 0.0538(8) Uani 1 1 d . . .
H3 H 0.4120 0.0865 0.4467 0.065 Uiso 1 1 calc R . .
C4 C 0.5515(2) 0.0995(2) 0.4320(2) 0.0477(7) Uani 1 1 d . . .
H4 H 0.5607 0.0407 0.4110 0.057 Uiso 1 1 calc R . .
C5 C 0.6267(2) 0.16193(18) 0.44223(18) 0.0381(7) Uani 1 1 d . . .
C6 C 0.7746(2) 0.21983(18) 0.43957(18) 0.0380(7) Uani 1 1 d . . .
C7 C 0.9068(2) 0.30262(19) 0.44653(19) 0.0420(7) Uani 1 1 d . . .
C8 C 1.0095(2) 0.31685(18) 0.43814(19) 0.0403(7) Uani 1 1 d . . .
C9 C 1.0446(3) 0.4047(2) 0.4323(2) 0.0545(8) Uani 1 1 d . . .
H9 H 1.0024 0.4536 0.4316 0.065 Uiso 1 1 calc R . .
C10 C 1.1414(3) 0.4197(2) 0.4277(2) 0.0590(9) Uani 1 1 d . . .
H10 H 1.1641 0.4786 0.4232 0.071 Uiso 1 1 calc R . .
C11 C 1.2046(2) 0.3472(2) 0.4297(2) 0.0568(9) Uani 1 1 d . . .
H11 H 1.2698 0.3573 0.4262 0.068 Uiso 1 1 calc R . .
C12 C 1.1707(2) 0.2600(2) 0.4370(2) 0.0492(8) Uani 1 1 d . . .
H12 H 1.2135 0.2114 0.4399 0.059 Uiso 1 1 calc R . .
C13 C 1.0738(2) 0.24460(19) 0.43988(19) 0.0435(7) Uani 1 1 d . . .
H13 H 1.0512 0.1855 0.4430 0.052 Uiso 1 1 calc R . .
C14 C 0.5171(2) 0.3716(2) 0.5270(2) 0.0658(10) Uani 1 1 d . . .
H14A H 0.5786 0.4010 0.5280 0.099 Uiso 1 1 calc R . .
H14B H 0.4990 0.3729 0.5910 0.099 Uiso 1 1 calc R . .
H14C H 0.4688 0.4025 0.4824 0.099 Uiso 1 1 calc R . .
S1B S 0.73873(5) -0.25979(5) 0.29044(5) 0.04064(18) Uani 1 1 d . . .
N1B N 0.86431(16) -0.23085(14) 0.31165(15) 0.0363(5) Uani 1 1 d . . .
N2B N 0.79525(16) -0.09409(14) 0.33380(15) 0.0367(5) Uani 1 1 d . . .
N3B N 0.62789(17) -0.11136(15) 0.30464(16) 0.0412(6) Uani 1 1 d . . .
O1B O 0.58015(14) -0.25721(13) 0.27025(14) 0.0482(5) Uani 1 1 d . . .
C1B C 0.9392(2) -0.28973(19) 0.30663(19) 0.0397(7) Uani 1 1 d . . .
C2B C 1.0309(2) -0.2561(2) 0.3244(2) 0.0475(8) Uani 1 1 d . . .
H2B H 1.0832 -0.2943 0.3200 0.057 Uiso 1 1 calc R . .
C3B C 1.0477(2) -0.1656(2) 0.3492(2) 0.0463(7) Uani 1 1 d . . .
H3B H 1.1110 -0.1443 0.3625 0.056 Uiso 1 1 calc R . .
C4B C 0.9725(2) -0.10756(19) 0.35432(19) 0.0419(7) Uani 1 1 d . . .
H4B H 0.9836 -0.0470 0.3710 0.050 Uiso 1 1 calc R . .
C5B C 0.8787(2) -0.14160(17) 0.33385(18) 0.0346(6) Uani 1 1 d . . .
C6B C 0.7167(2) -0.14479(18) 0.31090(18) 0.0363(6) Uani 1 1 d . . .
C7B C 0.5588(2) -0.1752(2) 0.28049(19) 0.0412(7) Uani 1 1 d . . .
C8B C 0.4574(2) -0.14391(19) 0.26736(19) 0.0385(7) Uani 1 1 d . . .
C9B C 0.3826(2) -0.20438(19) 0.27550(19) 0.0426(7) Uani 1 1 d . . .
H9B H 0.3964 -0.2656 0.2858 0.051 Uiso 1 1 calc R . .
C10B C 0.2886(2) -0.1744(2) 0.2685(2) 0.0492(8) Uani 1 1 d . . .
H10B H 0.2389 -0.2151 0.2749 0.059 Uiso 1 1 calc R . .
C11B C 0.2682(2) -0.0843(2) 0.2520(2) 0.0562(9) Uani 1 1 d . . .
H11B H 0.2047 -0.0638 0.2480 0.067 Uiso 1 1 calc R . .
C12B C 0.3411(2) -0.0240(2) 0.2415(2) 0.0588(9) Uani 1 1 d . . .
H12B H 0.3264 0.0368 0.2288 0.071 Uiso 1 1 calc R . .
C13B C 0.4360(2) -0.0532(2) 0.2498(2) 0.0499(8) Uani 1 1 d . . .
H13A H 0.4853 -0.0122 0.2436 0.060 Uiso 1 1 calc R . .
C14B C 0.9141(2) -0.38658(19) 0.2834(2) 0.0557(9) Uani 1 1 d . . .
H14D H 0.8450 -0.3938 0.2742 0.084 Uiso 1 1 calc R . .
H14E H 0.9427 -0.4244 0.3362 0.084 Uiso 1 1 calc R . .
H14F H 0.9385 -0.4038 0.2250 0.084 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
Cu1 N2 1.990(2) . ?
Cu1 N2B 1.996(2) . ?
Cu1 Cl1 2.2356(10) . ?
Cu1 Cl2 2.2544(10) . ?
S1 C6 1.747(3) . ?
S1 N1 1.809(2) . ?
S1 O1 2.076(2) . ?
N1 C5 1.353(3) . ?
N1 C1 1.368(3) . ?
N2 C6 1.331(3) . ?
N2 C5 1.363(3) . ?
N3 C6 1.331(3) . ?
N3 C7 1.344(3) . ?
O1 C7 1.275(3) . ?
C1 C2 1.363(4) . ?
C1 C14 1.491(4) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C7 C8 1.469(4) . ?
C8 C13 1.391(4) . ?
C8 C9 1.391(4) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
S1B C6B 1.754(3) . ?
S1B N1B 1.784(2) . ?
S1B O1B 2.188(2) . ?
N1B C5B 1.360(3) . ?
N1B C1B 1.368(3) . ?
N2B C6B 1.325(3) . ?
N2B C5B 1.359(3) . ?
N3B C6B 1.324(3) . ?
N3B C7B 1.354(3) . ?
O1B C7B 1.259(3) . ?
C1B C2B 1.359(4) . ?
C1B C14B 1.495(4) . ?
C2B C3B 1.390(4) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.364(4) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.390(4) . ?
C4B H4B 0.9300 . ?
C7B C8B 1.473(4) . ?
C8B C13B 1.385(4) . ?
C8B C9B 1.389(4) . ?
C9B C10B 1.374(4) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.372(4) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.375(4) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.380(4) . ?
C12B H12B 0.9300 . ?
C13B H13A 0.9300 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?

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
N2 Cu1 N2B 168.33(9) . . ?
N2 Cu1 Cl1 91.92(7) . . ?
N2B Cu1 Cl1 91.37(7) . . ?
N2 Cu1 Cl2 89.74(7) . . ?
N2B Cu1 Cl2 88.55(7) . . ?
Cl1 Cu1 Cl2 171.94(4) . . ?
C6 S1 N1 85.60(13) . . ?
C6 S1 O1 80.43(12) . . ?
N1 S1 O1 165.97(10) . . ?
C5 N1 C1 122.6(3) . . ?
C5 N1 S1 112.13(19) . . ?
C1 N1 S1 125.2(2) . . ?
C6 N2 C5 112.4(2) . . ?
C6 N2 Cu1 120.98(19) . . ?
C5 N2 Cu1 126.64(19) . . ?
C6 N3 C7 110.8(2) . . ?
C7 O1 S1 106.36(18) . . ?
C2 C1 N1 117.5(3) . . ?
C2 C1 C14 125.0(3) . . ?
N1 C1 C14 117.5(3) . . ?
C1 C2 C3 120.9(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.0(3) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
N1 C5 N2 113.8(2) . . ?
N1 C5 C4 120.1(3) . . ?
N2 C5 C4 126.1(3) . . ?
N2 C6 N3 122.7(2) . . ?
N2 C6 S1 116.1(2) . . ?
N3 C6 S1 121.2(2) . . ?
O1 C7 N3 121.2(3) . . ?
O1 C7 C8 119.6(3) . . ?
N3 C7 C8 119.2(3) . . ?
C13 C8 C9 118.9(3) . . ?
C13 C8 C7 121.5(3) . . ?
C9 C8 C7 119.5(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6B S1B N1B 86.16(12) . . ?
C6B S1B O1B 78.82(11) . . ?
N1B S1B O1B 164.97(9) . . ?
C5B N1B C1B 122.5(2) . . ?
C5B N1B S1B 112.17(18) . . ?
C1B N1B S1B 125.30(19) . . ?
C6B N2B C5B 112.7(2) . . ?
C6B N2B Cu1 114.82(18) . . ?
C5B N2B Cu1 131.95(18) . . ?
C6B N3B C7B 112.4(2) . . ?
C7B O1B S1B 104.71(17) . . ?
C2B C1B N1B 117.6(3) . . ?
C2B C1B C14B 124.9(3) . . ?
N1B C1B C14B 117.5(3) . . ?
C1B C2B C3B 120.9(3) . . ?
C1B C2B H2B 119.5 . . ?
C3B C2B H2B 119.5 . . ?
C4B C3B C2B 120.9(3) . . ?
C4B C3B H3B 119.5 . . ?
C2B C3B H3B 119.5 . . ?
C3B C4B C5B 118.0(3) . . ?
C3B C4B H4B 121.0 . . ?
C5B C4B H4B 121.0 . . ?
N2B C5B N1B 113.7(2) . . ?
N2B C5B C4B 126.4(2) . . ?
N1B C5B C4B 119.9(2) . . ?
N3B C6B N2B 122.5(2) . . ?
N3B C6B S1B 122.3(2) . . ?
N2B C6B S1B 115.2(2) . . ?
O1B C7B N3B 121.7(3) . . ?
O1B C7B C8B 121.8(3) . . ?
N3B C7B C8B 116.6(2) . . ?
C13B C8B C9B 119.4(3) . . ?
C13B C8B C7B 120.2(3) . . ?
C9B C8B C7B 120.4(3) . . ?
C10B C9B C8B 120.5(3) . . ?
C10B C9B H9B 119.7 . . ?
C8B C9B H9B 119.7 . . ?
C11B C10B C9B 119.7(3) . . ?
C11B C10B H10B 120.2 . . ?
C9B C10B H10B 120.2 . . ?
C10B C11B C12B 120.5(3) . . ?
C10B C11B H11B 119.8 . . ?
C12B C11B H11B 119.8 . . ?
C11B C12B C13B 120.3(3) . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B H12B 119.9 . . ?
C12B C13B C8B 119.7(3) . . ?
C12B C13B H13A 120.2 . . ?
C8B C13B H13A 120.2 . . ?
C1B C14B H14D 109.5 . . ?
C1B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C1B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 714501'
#######################################################################
#
#                 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_compound2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N3 O S'
_chemical_formula_sum            'C14 H13 N3 O S'
_chemical_formula_weight         271.33

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc '


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

_cell_length_a                   12.018(4)
_cell_length_b                   5.2813(16)
_cell_length_c                   21.723(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.502(4)
_cell_angle_gamma                90.00
_cell_volume                     1367.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    26
_cell_measurement_theta_min      4
_cell_measurement_theta_max      23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   Psi-Scans
_exptl_absorpt_correction_T_min  0.8
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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 CCD area-detector'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10289
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         30.36
_reflns_number_total             3931
_reflns_number_gt                1681
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (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)+(0.0580P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3931
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_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 0.47177(4) 0.18304(13) 0.41388(2) 0.0776(2) Uani 1 1 d . . .
N1 N 0.13114(13) 0.4067(3) 0.30794(8) 0.0728(5) Uani 1 1 d . . .
N2 N 0.24939(12) 0.2066(3) 0.37980(7) 0.0576(4) Uani 1 1 d . . .
H2 H 0.1866 0.1433 0.3872 0.069 Uiso 1 1 calc R . .
N3 N 0.31220(11) -0.0713(3) 0.45712(6) 0.0544(4) Uani 1 1 d . . .
H3 H 0.3687 -0.1436 0.4785 0.065 Uiso 1 1 calc R . .
O1 O 0.12171(10) -0.0673(3) 0.44093(7) 0.0814(4) Uani 1 1 d . . .
C1 C 0.10792(19) 0.5773(5) 0.26293(11) 0.0884(7) Uani 1 1 d . . .
H1 H 0.0339 0.5917 0.2444 0.106 Uiso 1 1 calc R . .
C2 C 0.1862(2) 0.7324(4) 0.24239(10) 0.0788(7) Uani 1 1 d . . .
H2A H 0.1652 0.8492 0.2110 0.095 Uiso 1 1 calc R . .
C3 C 0.29594(18) 0.7145(4) 0.26850(9) 0.0619(5) Uani 1 1 d . . .
C4 C 0.32220(15) 0.5402(3) 0.31549(8) 0.0571(5) Uani 1 1 d . . .
H4 H 0.3955 0.5238 0.3349 0.069 Uiso 1 1 calc R . .
C5 C 0.23785(14) 0.3913(3) 0.33299(8) 0.0524(4) Uani 1 1 d . . .
C6 C 0.33845(13) 0.1093(3) 0.41520(8) 0.0517(5) Uani 1 1 d . . .
C7 C 0.20792(15) -0.1519(4) 0.46945(9) 0.0578(5) Uani 1 1 d . . .
C8 C 0.20536(14) -0.3432(3) 0.51874(8) 0.0526(4) Uani 1 1 d . . .
C9 C 0.10815(16) -0.3603(4) 0.54657(9) 0.0647(5) Uani 1 1 d . . .
H9 H 0.0494 -0.2479 0.5353 0.078 Uiso 1 1 calc R . .
C10 C 0.0981(2) -0.5424(5) 0.59066(9) 0.0764(6) Uani 1 1 d . . .
H10 H 0.0327 -0.5529 0.6091 0.092 Uiso 1 1 calc R . .
C11 C 0.1835(2) -0.7071(4) 0.60740(10) 0.0814(7) Uani 1 1 d . . .
H11 H 0.1761 -0.8305 0.6371 0.098 Uiso 1 1 calc R . .
C12 C 0.2812(2) -0.6923(4) 0.58062(10) 0.0788(6) Uani 1 1 d . . .
H12 H 0.3397 -0.8044 0.5925 0.095 Uiso 1 1 calc R . .
C13 C 0.29173(17) -0.5105(4) 0.53616(9) 0.0632(5) Uani 1 1 d . . .
H13 H 0.3574 -0.5009 0.5179 0.076 Uiso 1 1 calc R . .
C14 C 0.38571(19) 0.8794(4) 0.24725(11) 0.0878(7) Uani 1 1 d . . .
H14A H 0.3530 0.9871 0.2141 0.132 Uiso 1 1 calc R . .
H14B H 0.4422 0.7747 0.2328 0.132 Uiso 1 1 calc R . .
H14C H 0.4192 0.9814 0.2813 0.132 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 C6 1.6528(18) . ?
N1 C5 1.329(2) . ?
N1 C1 1.332(3) . ?
N2 C6 1.336(2) . ?
N2 C5 1.403(2) . ?
N2 H2 0.8600 . ?
N3 C7 1.382(2) . ?
N3 C6 1.383(2) . ?
N3 H3 0.8600 . ?
O1 C7 1.220(2) . ?
C1 C2 1.366(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.380(2) . ?
C3 C14 1.505(3) . ?
C4 C5 1.375(2) . ?
C4 H4 0.9300 . ?
C7 C8 1.476(3) . ?
C8 C13 1.378(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C5 N1 C1 116.13(18) . . ?
C6 N2 C5 132.88(15) . . ?
C6 N2 H2 113.6 . . ?
C5 N2 H2 113.6 . . ?
C7 N3 C6 129.06(15) . . ?
C7 N3 H3 115.5 . . ?
C6 N3 H3 115.5 . . ?
N1 C1 C2 123.9(2) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 119.38(19) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 C4 117.88(19) . . ?
C2 C3 C14 121.54(19) . . ?
C4 C3 C14 120.58(19) . . ?
C5 C4 C3 118.69(17) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 123.98(17) . . ?
N1 C5 N2 109.76(16) . . ?
C4 C5 N2 126.25(16) . . ?
N2 C6 N3 114.18(15) . . ?
N2 C6 S1 127.22(14) . . ?
N3 C6 S1 118.60(12) . . ?
O1 C7 N3 121.35(18) . . ?
O1 C7 C8 121.48(16) . . ?
N3 C7 C8 117.17(16) . . ?
C13 C8 C9 119.07(18) . . ?
C13 C8 C7 123.51(17) . . ?
C9 C8 C7 117.35(17) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 120.2(2) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        30.36
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 714502'
#######################################################################
#
#                 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_compound

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N3 O S'
_chemical_formula_weight         271.33

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn  '

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

_cell_length_a                   7.201(3)
_cell_length_b                   18.487(8)
_cell_length_c                   10.441(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.926(7)
_cell_angle_gamma                90.00
_cell_volume                     1314.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2001)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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 CCD area-detector'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8249
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         26.45
_reflns_number_total             2693
_reflns_number_gt                1670
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (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)+(0.0438P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2693
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_restrained_S_all      0.897
_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
S1 S 0.06564(9) 0.06550(3) 0.84822(6) 0.0606(2) Uani 1 1 d . . .
O1 O 0.0296(2) 0.20959(7) 0.71488(13) 0.0631(4) Uani 1 1 d . . .
N1 N 0.0392(2) 0.22081(7) 1.18679(14) 0.0391(4) Uani 1 1 d . . .
N2 N 0.0354(2) 0.10917(7) 1.07800(15) 0.0446(4) Uani 1 1 d . . .
H2 H 0.0130 0.0638 1.0841 0.054 Uiso 1 1 calc R . .
N3 N 0.0567(2) 0.20226(7) 0.93796(14) 0.0404(4) Uani 1 1 d . . .
H3 H 0.0638 0.2286 1.0072 0.049 Uiso 1 1 calc R . .
C1 C 0.0574(3) 0.25850(9) 1.30119(19) 0.0413(5) Uani 1 1 d . . .
C2 C 0.0871(3) 0.22446(10) 1.4227(2) 0.0484(5) Uani 1 1 d . . .
H2A H 0.1021 0.2514 1.5006 0.058 Uiso 1 1 calc R . .
C3 C 0.0944(3) 0.14995(10) 1.42894(19) 0.0496(5) Uani 1 1 d . . .
H3A H 0.1125 0.1264 1.5108 0.060 Uiso 1 1 calc R . .
C4 C 0.0750(3) 0.11107(10) 1.31420(18) 0.0454(5) Uani 1 1 d . . .
H4 H 0.0786 0.0608 1.3157 0.054 Uiso 1 1 calc R . .
C5 C 0.0498(3) 0.14906(9) 1.19558(18) 0.0380(4) Uani 1 1 d . . .
C6 C 0.0506(3) 0.12924(9) 0.95666(18) 0.0395(5) Uani 1 1 d . . .
C7 C 0.0529(3) 0.23942(9) 0.82116(18) 0.0391(5) Uani 1 1 d . . .
C8 C 0.0748(2) 0.31947(9) 0.83656(18) 0.0374(4) Uani 1 1 d . . .
C9 C 0.1487(3) 0.35389(9) 0.9598(2) 0.0461(5) Uani 1 1 d . . .
H9 H 0.1861 0.3269 1.0393 0.055 Uiso 1 1 calc R . .
C10 C 0.1675(3) 0.42820(10) 0.9657(2) 0.0619(6) Uani 1 1 d . . .
H10 H 0.2167 0.4512 1.0492 0.074 Uiso 1 1 calc R . .
C11 C 0.1139(3) 0.46815(11) 0.8490(3) 0.0696(7) Uani 1 1 d . . .
H11 H 0.1263 0.5182 0.8533 0.083 Uiso 1 1 calc R . .
C12 C 0.0424(3) 0.43472(11) 0.7265(2) 0.0646(6) Uani 1 1 d . . .
H12 H 0.0066 0.4620 0.6474 0.078 Uiso 1 1 calc R . .
C13 C 0.0232(3) 0.36073(10) 0.7198(2) 0.0489(5) Uani 1 1 d . . .
H13 H -0.0251 0.3382 0.6358 0.059 Uiso 1 1 calc R . .
C14 C 0.0380(3) 0.33914(10) 1.2869(2) 0.0566(6) Uani 1 1 d . . .
H14A H 0.0670 0.3607 1.3749 0.085 Uiso 1 1 calc R . .
H14B H -0.0936 0.3513 1.2327 0.085 Uiso 1 1 calc R . .
H15C H 0.1283 0.3570 1.2440 0.085 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 C6 1.6619(18) . ?
O1 C7 1.2012(19) . ?
N1 C5 1.330(2) . ?
N1 C1 1.352(2) . ?
N2 C6 1.358(2) . ?
N2 C5 1.407(2) . ?
N2 H2 0.8600 . ?
N3 C6 1.367(2) . ?
N3 C7 1.392(2) . ?
N3 H3 0.8600 . ?
C1 C2 1.370(3) . ?
C1 C14 1.500(2) . ?
C2 C3 1.379(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.365(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9300 . ?
C7 C8 1.491(2) . ?
C8 C9 1.379(2) . ?
C8 C13 1.383(2) . ?
C9 C10 1.380(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H15C 0.9600 . ?

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
C5 N1 C1 117.78(15) . . ?
C6 N2 C5 131.71(14) . . ?
C6 N2 H2 114.1 . . ?
C5 N2 H2 114.1 . . ?
C6 N3 C7 128.32(15) . . ?
C6 N3 H3 115.8 . . ?
C7 N3 H3 115.8 . . ?
N1 C1 C2 121.54(17) . . ?
N1 C1 C14 116.44(16) . . ?
C2 C1 C14 122.00(17) . . ?
C1 C2 C3 119.63(18) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 119.57(18) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 117.68(18) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
N1 C5 C4 123.78(16) . . ?
N1 C5 N2 118.44(15) . . ?
C4 C5 N2 117.78(16) . . ?
N2 C6 N3 114.79(14) . . ?
N2 C6 S1 118.99(13) . . ?
N3 C6 S1 126.21(13) . . ?
O1 C7 N3 122.68(16) . . ?
O1 C7 C8 122.23(16) . . ?
N3 C7 C8 115.07(15) . . ?
C9 C8 C13 118.73(17) . . ?
C9 C8 C7 123.64(16) . . ?
C13 C8 C7 117.60(16) . . ?
C8 C9 C10 120.25(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.66(19) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H15C 109.5 . . ?
H14A C14 H15C 109.5 . . ?
H14B C14 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.45
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 714503'
#######################################################################
#
#                 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_fe212

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N3 O S'
_chemical_formula_weight         269.32

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc '


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

_cell_length_a                   12.7107(7)
_cell_length_b                   18.0290(9)
_cell_length_c                   11.5181(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.980(3)
_cell_angle_gamma                90.00
_cell_volume                     2582.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    263
_cell_measurement_theta_min      4.2
_cell_measurement_theta_max      27.3

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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 CCD area-detector'
_diffrn_measurement_method       ω/2θ

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27749
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         24.76
_reflns_number_total             4378
_reflns_number_gt                3099
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'SHELXTL (Bruker, 2001), ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (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)+(0.0591P)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_number_reflns         4378
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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 -0.07216(4) 0.01837(3) 0.26146(5) 0.05326(18) Uani 1 1 d . . .
O1 O -0.08650(14) 0.09687(8) 0.40476(14) 0.0670(4) Uani 1 1 d . . .
N1 N -0.02435(14) -0.04131(8) 0.16141(14) 0.0467(4) Uani 1 1 d . . .
N2 N 0.13495(14) -0.00434(9) 0.27960(16) 0.0564(5) Uani 1 1 d . . .
N3 N 0.09325(15) 0.07573(9) 0.42364(15) 0.0554(5) Uani 1 1 d . . .
C1 C 0.08529(18) -0.04519(11) 0.18626(19) 0.0518(5) Uani 1 1 d . . .
C2 C 0.06439(17) 0.03162(11) 0.32786(18) 0.0502(5) Uani 1 1 d . . .
C3 C 0.0091(2) 0.10729(11) 0.4587(2) 0.0544(6) Uani 1 1 d . . .
C4 C 0.0339(2) 0.15571(11) 0.56547(19) 0.0561(6) Uani 1 1 d . . .
C5 C -0.0488(2) 0.18701(12) 0.6113(2) 0.0714(7) Uani 1 1 d . . .
H5 H -0.1201 0.1779 0.5751 0.086 Uiso 1 1 calc R . .
C6 C -0.0249(3) 0.23200(15) 0.7115(3) 0.0876(9) Uani 1 1 d . . .
H6 H -0.0803 0.2530 0.7421 0.105 Uiso 1 1 calc R . .
C7 C 0.0792(3) 0.24529(15) 0.7646(3) 0.0945(10) Uani 1 1 d . . .
H7 H 0.0948 0.2756 0.8313 0.113 Uiso 1 1 calc R . .
C8 C 0.1616(3) 0.21422(14) 0.7205(2) 0.0857(8) Uani 1 1 d . . .
H8 H 0.2327 0.2234 0.7575 0.103 Uiso 1 1 calc R . .
C9 C 0.1387(2) 0.16970(12) 0.6220(2) 0.0699(7) Uani 1 1 d . . .
H9 H 0.1947 0.1486 0.5928 0.084 Uiso 1 1 calc R . .
C10 C 0.13634(19) -0.08929(11) 0.1147(2) 0.0595(6) Uani 1 1 d . . .
H10 H 0.2109 -0.0933 0.1307 0.071 Uiso 1 1 calc R . .
C11 C 0.0758(2) -0.12609(12) 0.0219(2) 0.0660(7) Uani 1 1 d . . .
H11 H 0.1092 -0.1548 -0.0271 0.079 Uiso 1 1 calc R . .
C12 C -0.0366(2) -0.12139(12) -0.00107(19) 0.0609(6) Uani 1 1 d . . .
H12 H -0.0772 -0.1473 -0.0647 0.073 Uiso 1 1 calc R . .
C13 C -0.08684(18) -0.07929(11) 0.06896(19) 0.0534(6) Uani 1 1 d . . .
C14 C -0.20545(18) -0.07190(13) 0.0538(2) 0.0708(7) Uani 1 1 d . . .
H14A H -0.2403 -0.1017 -0.0121 0.106 Uiso 1 1 calc R . .
H14B H -0.2256 -0.0209 0.0390 0.106 Uiso 1 1 calc R . .
H14C H -0.2270 -0.0883 0.1247 0.106 Uiso 1 1 calc R . .
S2 S 0.56835(4) 0.49498(3) 0.31313(5) 0.05266(18) Uani 1 1 d . . .
O2 O 0.62879(12) 0.43418(8) 0.47265(13) 0.0618(4) Uani 1 1 d . . .
N4 N 0.49005(14) 0.53212(9) 0.18037(14) 0.0492(4) Uani 1 1 d . . .
N5 N 0.37086(15) 0.44849(10) 0.23207(16) 0.0596(5) Uani 1 1 d . . .
N6 N 0.45778(15) 0.39121(9) 0.40931(16) 0.0556(5) Uani 1 1 d . . .
C15 C 0.38995(18) 0.50054(12) 0.1541(2) 0.0540(6) Uani 1 1 d . . .
C16 C 0.45441(17) 0.43950(11) 0.3190(2) 0.0513(5) Uani 1 1 d . . .
C17 C 0.55169(19) 0.39253(11) 0.48677(19) 0.0530(6) Uani 1 1 d . . .
C18 C 0.56817(18) 0.34300(11) 0.59188(19) 0.0531(6) Uani 1 1 d . . .
C19 C 0.4884(2) 0.29424(12) 0.6103(2) 0.0663(7) Uani 1 1 d . . .
H19 H 0.4229 0.2924 0.5564 0.080 Uiso 1 1 calc R . .
C20 C 0.5065(2) 0.24849(13) 0.7090(3) 0.0780(8) Uani 1 1 d . . .
H20 H 0.4529 0.2160 0.7211 0.094 Uiso 1 1 calc R . .
C21 C 0.6024(3) 0.25073(14) 0.7889(2) 0.0836(8) Uani 1 1 d . . .
H21 H 0.6141 0.2196 0.8547 0.100 Uiso 1 1 calc R . .
C22 C 0.6824(2) 0.29943(15) 0.7719(2) 0.0811(8) Uani 1 1 d . . .
H22 H 0.7475 0.3015 0.8264 0.097 Uiso 1 1 calc R . .
C23 C 0.6645(2) 0.34490(13) 0.6731(2) 0.0675(7) Uani 1 1 d . . .
H23 H 0.7182 0.3773 0.6613 0.081 Uiso 1 1 calc R . .
C24 C 0.3180(2) 0.52307(13) 0.0516(2) 0.0650(6) Uani 1 1 d . . .
H24 H 0.2492 0.5031 0.0323 0.078 Uiso 1 1 calc R . .
C25 C 0.3505(2) 0.57498(13) -0.0199(2) 0.0701(7) Uani 1 1 d . . .
H25 H 0.3035 0.5900 -0.0890 0.084 Uiso 1 1 calc R . .
C26 C 0.4538(2) 0.60592(12) 0.0099(2) 0.0656(6) Uani 1 1 d . . .
H26 H 0.4747 0.6413 -0.0396 0.079 Uiso 1 1 calc R . .
C27 C 0.52380(19) 0.58470(11) 0.1106(2) 0.0559(6) Uani 1 1 d . . .
C28 C 0.63493(18) 0.61492(12) 0.1502(2) 0.0679(7) Uani 1 1 d . . .
H28A H 0.6495 0.6498 0.0925 0.102 Uiso 1 1 calc R . .
H28B H 0.6860 0.5750 0.1583 0.102 Uiso 1 1 calc R . .
H28C H 0.6407 0.6394 0.2253 0.102 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 C2 1.762(2) . ?
S1 N1 1.7736(17) . ?
O1 C3 1.259(3) . ?
N1 C1 1.365(3) . ?
N1 C13 1.372(3) . ?
N2 C2 1.319(3) . ?
N2 C1 1.347(3) . ?
N3 C3 1.345(3) . ?
N3 C2 1.348(3) . ?
C1 C10 1.398(3) . ?
C3 C4 1.488(3) . ?
C4 C9 1.378(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.359(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.354(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.400(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.487(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
S2 C16 1.773(2) . ?
S2 N4 1.7735(18) . ?
S2 O2 2.1406(15) . ?
O2 C17 1.272(2) . ?
N4 C27 1.368(3) . ?
N4 C15 1.369(3) . ?
N5 C16 1.309(3) . ?
N5 C15 1.356(3) . ?
N6 C17 1.334(3) . ?
N6 C16 1.351(3) . ?
C15 C24 1.395(3) . ?
C17 C18 1.484(3) . ?
C18 C23 1.378(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.366(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.403(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.362(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.494(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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 S1 N1 85.69(9) . . ?
C1 N1 C13 122.57(18) . . ?
C1 N1 S1 111.56(14) . . ?
C13 N1 S1 125.86(15) . . ?
C2 N2 C1 110.98(19) . . ?
C3 N3 C2 113.39(19) . . ?
N2 C1 N1 115.34(18) . . ?
N2 C1 C10 125.7(2) . . ?
N1 C1 C10 119.0(2) . . ?
N2 C2 N3 122.8(2) . . ?
N2 C2 S1 116.42(16) . . ?
N3 C2 S1 120.78(16) . . ?
O1 C3 N3 122.4(2) . . ?
O1 C3 C4 120.8(2) . . ?
N3 C3 C4 116.8(2) . . ?
C9 C4 C5 118.6(2) . . ?
C9 C4 C3 121.1(2) . . ?
C5 C4 C3 120.3(2) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 121.1(3) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C11 C10 C1 119.1(2) . . ?
C11 C10 H10 120.4 . . ?
C1 C10 H10 120.4 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 N1 118.1(2) . . ?
C12 C13 C14 124.7(2) . . ?
N1 C13 C14 117.11(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 S2 N4 85.93(10) . . ?
C16 S2 O2 80.16(9) . . ?
N4 S2 O2 166.08(8) . . ?
C17 O2 S2 105.27(14) . . ?
C27 N4 C15 123.2(2) . . ?
C27 N4 S2 125.45(16) . . ?
C15 N4 S2 111.30(15) . . ?
C16 N5 C15 111.34(18) . . ?
C17 N6 C16 112.63(18) . . ?
N5 C15 N4 115.3(2) . . ?
N5 C15 C24 125.9(2) . . ?
N4 C15 C24 118.8(2) . . ?
N5 C16 N6 124.03(19) . . ?
N5 C16 S2 116.15(17) . . ?
N6 C16 S2 119.82(17) . . ?
O2 C17 N6 122.1(2) . . ?
O2 C17 C18 118.5(2) . . ?
N6 C17 C18 119.4(2) . . ?
C23 C18 C19 119.0(2) . . ?
C23 C18 C17 119.6(2) . . ?
C19 C18 C17 121.4(2) . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C18 C23 C22 121.0(2) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C15 118.9(2) . . ?
C25 C24 H24 120.6 . . ?
C15 C24 H24 120.6 . . ?
C24 C25 C26 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 N4 117.8(2) . . ?
C26 C27 C28 124.5(2) . . ?
N4 C27 C28 117.7(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
C2 S1 N1 C1 -0.21(14) . . . . ?
C2 S1 N1 C13 -179.67(17) . . . . ?
C2 N2 C1 N1 -0.1(3) . . . . ?
C2 N2 C1 C10 179.3(2) . . . . ?
C13 N1 C1 N2 179.69(17) . . . . ?
S1 N1 C1 N2 0.2(2) . . . . ?
C13 N1 C1 C10 0.2(3) . . . . ?
S1 N1 C1 C10 -179.24(15) . . . . ?
C1 N2 C2 N3 179.14(18) . . . . ?
C1 N2 C2 S1 -0.1(2) . . . . ?
C3 N3 C2 N2 179.91(18) . . . . ?
C3 N3 C2 S1 -0.9(2) . . . . ?
N1 S1 C2 N2 0.18(16) . . . . ?
N1 S1 C2 N3 -179.08(17) . . . . ?
C2 N3 C3 O1 -1.1(3) . . . . ?
C2 N3 C3 C4 178.81(16) . . . . ?
O1 C3 C4 C9 -177.3(2) . . . . ?
N3 C3 C4 C9 2.7(3) . . . . ?
O1 C3 C4 C5 3.6(3) . . . . ?
N3 C3 C4 C5 -176.36(18) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
C3 C4 C5 C6 179.8(2) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
C5 C4 C9 C8 -0.8(3) . . . . ?
C3 C4 C9 C8 -179.9(2) . . . . ?
N2 C1 C10 C11 -178.5(2) . . . . ?
N1 C1 C10 C11 0.9(3) . . . . ?
C1 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 N1 0.6(3) . . . . ?
C11 C12 C13 C14 -178.6(2) . . . . ?
C1 N1 C13 C12 -1.0(3) . . . . ?
S1 N1 C13 C12 178.41(14) . . . . ?
C1 N1 C13 C14 178.28(18) . . . . ?
S1 N1 C13 C14 -2.3(3) . . . . ?
C16 S2 O2 C17 -0.92(13) . . . . ?
N4 S2 O2 C17 -2.0(3) . . . . ?
C16 S2 N4 C27 -179.13(16) . . . . ?
O2 S2 N4 C27 -178.1(2) . . . . ?
C16 S2 N4 C15 -0.07(14) . . . . ?
O2 S2 N4 C15 1.0(4) . . . . ?
C16 N5 C15 N4 0.4(2) . . . . ?
C16 N5 C15 C24 179.67(19) . . . . ?
C27 N4 C15 N5 178.93(17) . . . . ?
S2 N4 C15 N5 -0.2(2) . . . . ?
C27 N4 C15 C24 -0.4(3) . . . . ?
S2 N4 C15 C24 -179.50(15) . . . . ?
C15 N5 C16 N6 179.94(18) . . . . ?
C15 N5 C16 S2 -0.5(2) . . . . ?
C17 N6 C16 N5 -179.83(18) . . . . ?
C17 N6 C16 S2 0.6(2) . . . . ?
N4 S2 C16 N5 0.31(16) . . . . ?
O2 S2 C16 N5 -179.43(16) . . . . ?
N4 S2 C16 N6 179.93(16) . . . . ?
O2 S2 C16 N6 0.19(15) . . . . ?
S2 O2 C17 N6 1.6(2) . . . . ?
S2 O2 C17 C18 -179.54(13) . . . . ?
C16 N6 C17 O2 -1.6(3) . . . . ?
C16 N6 C17 C18 179.57(16) . . . . ?
O2 C17 C18 C23 2.1(3) . . . . ?
N6 C17 C18 C23 -179.05(19) . . . . ?
O2 C17 C18 C19 -177.76(18) . . . . ?
N6 C17 C18 C19 1.1(3) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?
C17 C18 C19 C20 179.69(19) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
C17 C18 C23 C22 -179.9(2) . . . . ?
C21 C22 C23 C18 0.5(4) . . . . ?
N5 C15 C24 C25 -178.27(19) . . . . ?
N4 C15 C24 C25 1.0(3) . . . . ?
C15 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 N4 0.5(3) . . . . ?
C25 C26 C27 C28 -179.4(2) . . . . ?
C15 N4 C27 C26 -0.3(3) . . . . ?
S2 N4 C27 C26 178.61(15) . . . . ?
C15 N4 C27 C28 179.58(18) . . . . ?
S2 N4 C27 C28 -1.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        24.76
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 962672'
