# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_ndi2a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 N4 O4 S2'
_chemical_formula_sum            'C20 H12 N4 O4 S2'
_chemical_formula_weight         436.48

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   P2(1)/c
_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                   8.987(2)
_cell_length_b                   13.788(3)
_cell_length_c                   15.365(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.787(5)
_cell_angle_gamma                90.00
_cell_volume                     1849.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    2049
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      24.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   'SADBS; BRUKER, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14883
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.17
_reflns_number_total             3310
_reflns_number_gt                2472
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0464P)^2^+1.1540P] where P=(Fo^2^+2Fc^2^)/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         3310
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.7160(2) 0.81578(15) 0.42960(13) 0.0160(5) Uani 1 1 d . . .
N2 N 0.8982(3) 0.64634(18) 0.52863(18) 0.0337(6) Uani 1 1 d . . .
N3 N 0.2712(2) 0.56137(15) 0.28719(13) 0.0167(5) Uani 1 1 d . . .
N4 N 0.3786(3) 0.67173(16) 0.14896(15) 0.0230(5) Uani 1 1 d . . .
O1 O 0.4970(2) 0.73998(13) 0.35793(12) 0.0222(4) Uani 1 1 d . . .
O2 O 0.93548(19) 0.88612(13) 0.50862(12) 0.0216(4) Uani 1 1 d . . .
O3 O 0.4128(2) 0.46041(13) 0.22236(12) 0.0249(5) Uani 1 1 d . . .
O4 O 0.1294(2) 0.66195(13) 0.35250(12) 0.0223(4) Uani 1 1 d . . .
S1 S 1.03008(9) 0.59066(6) 0.70142(5) 0.0404(2) Uani 1 1 d . . .
S2 S 0.67607(8) 0.72218(6) 0.14987(5) 0.0312(2) Uani 1 1 d . . .
C1 C 0.5563(3) 0.80785(19) 0.40386(16) 0.0167(6) Uani 1 1 d . . .
C2 C 0.4666(3) 0.88499(18) 0.43462(16) 0.0147(5) Uani 1 1 d . . .
C3 C 0.3093(3) 0.88096(18) 0.41288(16) 0.0174(6) Uani 1 1 d . . .
H3 H 0.2595 0.8288 0.3801 0.021 Uiso 1 1 calc R . .
C4 C 0.5434(3) 0.96298(18) 0.48617(15) 0.0144(5) Uani 1 1 d . . .
C5 C 0.7043(3) 0.96775(18) 0.51087(16) 0.0153(5) Uani 1 1 d . . .
C6 C 0.7765(3) 1.04477(18) 0.56002(16) 0.0175(6) Uani 1 1 d . . .
H6 H 0.8829 1.0477 0.5755 0.021 Uiso 1 1 calc R . .
C7 C 0.7960(3) 0.88872(18) 0.48476(16) 0.0167(6) Uani 1 1 d . . .
C8 C 0.8050(3) 0.74389(19) 0.39311(18) 0.0214(6) Uani 1 1 d . . .
H8A H 0.9083 0.7683 0.3996 0.026 Uiso 1 1 calc R . .
H8B H 0.7597 0.7362 0.3296 0.026 Uiso 1 1 calc R . .
C9 C 0.8132(3) 0.6456(2) 0.43774(19) 0.0273(7) Uani 1 1 d . . .
H9A H 0.7099 0.6233 0.4354 0.033 Uiso 1 1 calc R . .
H9B H 0.8599 0.5998 0.4044 0.033 Uiso 1 1 calc R . .
C10 C 0.9514(3) 0.6204(2) 0.6018(2) 0.0304(7) Uani 1 1 d . . .
C11 C 0.3913(3) 0.49590(18) 0.29038(17) 0.0184(6) Uani 1 1 d . . .
C12 C 0.4892(3) 0.47274(18) 0.38023(16) 0.0160(5) Uani 1 1 d . . .
C13 C 0.6125(3) 0.41188(19) 0.38793(17) 0.0200(6) Uani 1 1 d . . .
H13 H 0.6361 0.3869 0.3366 0.024 Uiso 1 1 calc R . .
C14 C 0.7029(3) 0.38715(18) 0.47253(17) 0.0192(6) Uani 1 1 d . . .
H14 H 0.7858 0.3456 0.4768 0.023 Uiso 1 1 calc R . .
C15 C 0.4542(3) 0.51221(18) 0.45756(16) 0.0159(5) Uani 1 1 d . . .
C16 C 0.3293(3) 0.57652(18) 0.45075(17) 0.0167(6) Uani 1 1 d . . .
C17 C 0.2351(3) 0.60466(18) 0.36174(17) 0.0179(6) Uani 1 1 d . . .
C18 C 0.1745(3) 0.58592(19) 0.19884(17) 0.0194(6) Uani 1 1 d . . .
H18A H 0.0693 0.5933 0.2033 0.023 Uiso 1 1 calc R . .
H18B H 0.1779 0.5333 0.1574 0.023 Uiso 1 1 calc R . .
C19 C 0.2267(3) 0.67859(19) 0.16278(18) 0.0226(6) Uani 1 1 d . . .
H19A H 0.1561 0.6946 0.1064 0.027 Uiso 1 1 calc R . .
H19B H 0.2235 0.7309 0.2045 0.027 Uiso 1 1 calc R . .
C20 C 0.5043(3) 0.69413(19) 0.15138(17) 0.0220(6) Uani 1 1 d . . .

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
N1 0.0153(11) 0.0178(12) 0.0156(11) -0.0024(9) 0.0052(9) -0.0002(9)
N2 0.0313(14) 0.0299(15) 0.0402(17) 0.0088(12) 0.0091(13) 0.0048(12)
N3 0.0199(11) 0.0140(11) 0.0162(11) -0.0008(9) 0.0041(9) 0.0001(9)
N4 0.0249(13) 0.0231(13) 0.0210(12) 0.0009(10) 0.0057(10) -0.0043(10)
O1 0.0205(10) 0.0227(11) 0.0233(10) -0.0071(8) 0.0051(8) -0.0009(8)
O2 0.0131(9) 0.0246(11) 0.0270(11) -0.0014(8) 0.0046(8) 0.0010(8)
O3 0.0359(11) 0.0238(11) 0.0163(10) -0.0019(8) 0.0085(8) 0.0057(9)
O4 0.0196(10) 0.0216(10) 0.0252(10) -0.0006(8) 0.0046(8) 0.0028(8)
S1 0.0369(5) 0.0453(5) 0.0364(5) 0.0117(4) 0.0037(4) -0.0139(4)
S2 0.0258(4) 0.0446(5) 0.0254(4) -0.0115(3) 0.0103(3) -0.0064(3)
C1 0.0181(13) 0.0202(14) 0.0125(13) 0.0026(11) 0.0051(11) -0.0006(11)
C2 0.0151(13) 0.0192(14) 0.0100(13) 0.0036(10) 0.0035(10) -0.0008(10)
C3 0.0192(13) 0.0176(14) 0.0150(13) -0.0006(10) 0.0032(11) -0.0041(11)
C4 0.0157(13) 0.0186(14) 0.0097(12) 0.0033(10) 0.0044(10) -0.0015(10)
C5 0.0147(12) 0.0189(14) 0.0123(13) 0.0024(10) 0.0035(10) 0.0005(11)
C6 0.0139(13) 0.0209(14) 0.0176(14) 0.0011(11) 0.0033(11) -0.0017(11)
C7 0.0177(14) 0.0182(14) 0.0146(13) 0.0045(10) 0.0049(11) -0.0005(11)
C8 0.0182(13) 0.0264(16) 0.0211(15) -0.0071(11) 0.0073(11) 0.0017(12)
C9 0.0216(15) 0.0228(16) 0.0370(18) -0.0031(13) 0.0060(13) 0.0017(12)
C10 0.0275(16) 0.0210(16) 0.044(2) 0.0017(14) 0.0116(15) -0.0027(13)
C11 0.0226(14) 0.0158(14) 0.0183(14) -0.0009(11) 0.0081(11) -0.0031(11)
C12 0.0185(13) 0.0133(13) 0.0167(13) -0.0012(10) 0.0053(11) -0.0026(11)
C13 0.0262(15) 0.0189(15) 0.0171(14) -0.0042(11) 0.0095(12) 0.0007(12)
C14 0.0181(13) 0.0172(14) 0.0237(15) -0.0024(11) 0.0076(11) 0.0027(11)
C15 0.0181(13) 0.0136(13) 0.0176(13) -0.0027(10) 0.0073(11) -0.0040(10)
C16 0.0172(13) 0.0137(14) 0.0201(14) -0.0017(10) 0.0062(11) -0.0021(10)
C17 0.0168(13) 0.0164(14) 0.0212(14) -0.0020(11) 0.0058(11) -0.0035(11)
C18 0.0186(13) 0.0222(15) 0.0166(14) 0.0006(11) 0.0030(11) -0.0011(11)
C19 0.0220(14) 0.0240(15) 0.0211(15) 0.0030(11) 0.0035(12) 0.0015(12)
C20 0.0304(16) 0.0213(15) 0.0139(14) -0.0016(11) 0.0046(12) 0.0018(13)

_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
N1 C1 1.399(3) . ?
N1 C7 1.399(3) . ?
N1 C8 1.467(3) . ?
N2 C10 1.168(4) . ?
N2 C9 1.423(4) . ?
N3 C17 1.396(3) . ?
N3 C11 1.399(3) . ?
N3 C18 1.466(3) . ?
N4 C20 1.163(3) . ?
N4 C19 1.434(3) . ?
O1 C1 1.216(3) . ?
O2 C7 1.219(3) . ?
O3 C11 1.210(3) . ?
O4 C17 1.218(3) . ?
S1 C10 1.580(3) . ?
S2 C20 1.597(3) . ?
C1 C2 1.479(3) . ?
C2 C3 1.374(3) . ?
C2 C4 1.414(3) . ?
C3 C6 1.403(4) 3_676 ?
C3 H3 0.9300 . ?
C4 C5 1.406(3) . ?
C4 C4 1.411(5) 3_676 ?
C5 C6 1.373(3) . ?
C5 C7 1.479(3) . ?
C6 C3 1.403(4) 3_676 ?
C6 H6 0.9300 . ?
C8 C9 1.513(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.484(4) . ?
C12 C13 1.372(4) . ?
C12 C15 1.409(3) . ?
C13 C14 1.401(4) . ?
C13 H13 0.9300 . ?
C14 C16 1.374(3) 3_666 ?
C14 H14 0.9300 . ?
C15 C15 1.407(5) 3_666 ?
C15 C16 1.415(3) . ?
C16 C14 1.374(3) 3_666 ?
C16 C17 1.478(4) . ?
C18 C19 1.511(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 124.9(2) . . ?
C1 N1 C8 117.1(2) . . ?
C7 N1 C8 118.0(2) . . ?
C10 N2 C9 160.6(3) . . ?
C17 N3 C11 125.1(2) . . ?
C17 N3 C18 117.3(2) . . ?
C11 N3 C18 117.6(2) . . ?
C20 N4 C19 158.4(3) . . ?
O1 C1 N1 120.2(2) . . ?
O1 C1 C2 122.8(2) . . ?
N1 C1 C2 117.0(2) . . ?
C3 C2 C4 120.2(2) . . ?
C3 C2 C1 120.1(2) . . ?
C4 C2 C1 119.7(2) . . ?
C2 C3 C6 120.3(2) . 3_676 ?
C2 C3 H3 119.8 . . ?
C6 C3 H3 119.8 3_676 . ?
C5 C4 C4 119.5(3) . 3_676 ?
C5 C4 C2 121.3(2) . . ?
C4 C4 C2 119.2(3) 3_676 . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 C7 119.9(2) . . ?
C4 C5 C7 119.8(2) . . ?
C5 C6 C3 120.4(2) . 3_676 ?
C5 C6 H6 119.8 . . ?
C3 C6 H6 119.8 3_676 . ?
O2 C7 N1 120.3(2) . . ?
O2 C7 C5 122.7(2) . . ?
N1 C7 C5 117.0(2) . . ?
N1 C8 C9 113.8(2) . . ?
N1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
N2 C9 C8 113.3(2) . . ?
N2 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N2 C10 S1 176.6(3) . . ?
O3 C11 N3 120.7(2) . . ?
O3 C11 C12 122.3(2) . . ?
N3 C11 C12 116.9(2) . . ?
C13 C12 C15 120.1(2) . . ?
C13 C12 C11 119.9(2) . . ?
C15 C12 C11 120.0(2) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C16 C14 C13 120.9(2) 3_666 . ?
C16 C14 H14 119.6 3_666 . ?
C13 C14 H14 119.6 . . ?
C15 C15 C12 119.3(3) 3_666 . ?
C15 C15 C16 119.8(3) 3_666 . ?
C12 C15 C16 120.8(2) . . ?
C14 C16 C15 119.4(2) 3_666 . ?
C14 C16 C17 120.5(2) 3_666 . ?
C15 C16 C17 120.1(2) . . ?
O4 C17 N3 120.6(2) . . ?
O4 C17 C16 122.5(2) . . ?
N3 C17 C16 117.0(2) . . ?
N3 C18 C19 111.6(2) . . ?
N3 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
N3 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
N4 C19 C18 112.8(2) . . ?
N4 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
N4 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
N4 C20 S2 177.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.17
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 958704'