# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_mx59_13

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N4 O6 S2'
_chemical_formula_sum            'C22 H18 N4 O6 S2'
_chemical_formula_weight         498.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_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                   14.1494(7)
_cell_length_b                   5.0861(2)
_cell_length_c                   15.1825(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.108(5)
_cell_angle_gamma                90.00
_cell_volume                     1038.50(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4858
_cell_measurement_theta_min      3.0598
_cell_measurement_theta_max      66.8407

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    2.782
_exptl_absorpt_correction_T_min  0.76971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9925
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         66.95
_reflns_number_total             1841
_reflns_number_gt                1691
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0437P)²+0.5966P] 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         1841
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.52973(3) 0.19949(7) 0.60728(2) 0.01744(14) Uani 1 1 d . . .
O1 O 0.31493(8) -0.3220(2) 0.80685(8) 0.0212(3) Uani 1 1 d . . .
O2 O 0.58966(9) -0.8250(2) 0.92657(8) 0.0255(3) Uani 1 1 d . . .
O3 O 0.61020(8) -0.1646(2) 0.73271(8) 0.0250(3) Uani 1 1 d . . .
N1 N 0.45126(10) -0.5740(3) 0.86633(9) 0.0180(3) Uani 1 1 d . . .
N2 N 0.59980(10) -0.4942(3) 0.82976(9) 0.0191(3) Uani 1 1 d . . .
C1 C 0.47236(12) 0.4337(3) 0.52649(10) 0.0169(3) Uani 1 1 d . . .
C2 C 0.37387(12) 0.4687(3) 0.52081(11) 0.0203(3) Uani 1 1 d . . .
H2 H 0.3306 0.5898 0.4800 0.024 Uiso 1 1 calc R . .
C3 C 0.34510(12) 0.3058(3) 0.58195(11) 0.0194(3) Uani 1 1 d . . .
H3 H 0.2799 0.3058 0.5870 0.023 Uiso 1 1 calc R . .
C4 C 0.42072(12) 0.1433(3) 0.63478(11) 0.0173(3) Uani 1 1 d . . .
C5 C 0.40181(11) -0.0369(3) 0.69919(10) 0.0164(3) Uani 1 1 d . . .
H5 H 0.3357 -0.0233 0.7017 0.020 Uiso 1 1 calc R . .
C6 C 0.45533(11) -0.2241(3) 0.75808(10) 0.0163(3) Uani 1 1 d . . .
C7 C 0.40047(11) -0.3708(3) 0.81061(10) 0.0164(3) Uani 1 1 d . . .
C8 C 0.54918(12) -0.6438(3) 0.87713(11) 0.0185(3) Uani 1 1 d . . .
C9 C 0.55915(11) -0.2855(3) 0.77092(10) 0.0173(3) Uani 1 1 d . . .
C10 C 0.39545(13) -0.7276(3) 0.91595(12) 0.0234(4) Uani 1 1 d . . .
H10A H 0.4406 -0.8501 0.9587 0.035 Uiso 1 1 calc R . .
H10B H 0.3425 -0.8267 0.8712 0.035 Uiso 1 1 calc R . .
H10C H 0.3661 -0.6083 0.9510 0.035 Uiso 1 1 calc R . .
C11 C 0.70329(12) -0.5707(4) 0.84156(12) 0.0265(4) Uani 1 1 d . . .
H11A H 0.7292 -0.4651 0.8002 0.040 Uiso 1 1 calc R . .
H11B H 0.7057 -0.7574 0.8264 0.040 Uiso 1 1 calc R . .
H11C H 0.7439 -0.5404 0.9059 0.040 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0176(2) 0.0186(2) 0.0176(2) 0.00494(14) 0.00755(16) 0.00018(14)
O1 0.0186(6) 0.0223(6) 0.0255(6) 0.0046(4) 0.0112(5) 0.0005(4)
O2 0.0270(6) 0.0241(7) 0.0251(6) 0.0100(5) 0.0077(5) 0.0042(5)
O3 0.0198(6) 0.0272(7) 0.0307(7) 0.0117(5) 0.0119(5) 0.0015(5)
N1 0.0200(7) 0.0176(7) 0.0178(6) 0.0033(5) 0.0080(5) -0.0013(5)
N2 0.0177(7) 0.0202(7) 0.0202(7) 0.0040(5) 0.0069(5) 0.0011(5)
C1 0.0226(8) 0.0145(8) 0.0143(7) 0.0006(6) 0.0069(6) -0.0013(6)
C2 0.0225(8) 0.0190(8) 0.0196(8) 0.0050(6) 0.0070(6) 0.0018(6)
C3 0.0184(8) 0.0210(9) 0.0198(8) 0.0023(6) 0.0076(6) 0.0010(6)
C4 0.0190(8) 0.0171(8) 0.0167(7) -0.0014(6) 0.0071(6) -0.0015(6)
C5 0.0175(8) 0.0163(8) 0.0167(7) -0.0024(6) 0.0074(6) -0.0018(6)
C6 0.0191(8) 0.0153(8) 0.0158(8) -0.0007(6) 0.0073(6) -0.0025(6)
C7 0.0195(8) 0.0149(8) 0.0154(7) -0.0013(6) 0.0064(6) -0.0024(6)
C8 0.0219(8) 0.0181(8) 0.0156(7) 0.0001(6) 0.0060(6) -0.0016(6)
C9 0.0194(8) 0.0169(8) 0.0161(8) 0.0005(6) 0.0062(6) -0.0009(6)
C10 0.0273(9) 0.0237(9) 0.0232(8) 0.0069(7) 0.0136(7) -0.0022(7)
C11 0.0187(9) 0.0289(10) 0.0327(9) 0.0095(7) 0.0091(7) 0.0055(7)

_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 C1 1.7215(15) . ?
S1 C4 1.7422(15) . ?
O1 C7 1.2193(19) . ?
O2 C8 1.214(2) . ?
O3 C9 1.2236(19) . ?
N1 C7 1.386(2) . ?
N1 C8 1.390(2) . ?
N1 C10 1.4738(19) . ?
N2 C8 1.389(2) . ?
N2 C9 1.391(2) . ?
N2 C11 1.471(2) . ?
C1 C2 1.381(2) . ?
C1 C1 1.451(3) 3_666 ?
C2 C3 1.396(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.425(2) . ?
C5 C6 1.363(2) . ?
C6 C9 1.455(2) . ?
C6 C7 1.477(2) . ?

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 S1 C4 91.58(7) . . ?
C7 N1 C8 124.84(13) . . ?
C7 N1 C10 116.66(13) . . ?
C8 N1 C10 118.50(13) . . ?
C8 N2 C9 125.00(13) . . ?
C8 N2 C11 116.47(13) . . ?
C9 N2 C11 118.50(13) . . ?
C2 C1 C1 127.80(18) . 3_666 ?
C2 C1 S1 112.15(11) . . ?
C1 C1 S1 120.05(16) 3_666 . ?
C1 C2 C3 112.28(14) . . ?
C4 C3 C2 113.87(14) . . ?
C3 C4 C5 120.18(14) . . ?
C3 C4 S1 110.11(11) . . ?
C5 C4 S1 129.71(12) . . ?
C6 C5 C4 135.63(14) . . ?
C5 C6 C9 124.75(14) . . ?
C5 C6 C7 115.41(14) . . ?
C9 C6 C7 119.84(14) . . ?
O1 C7 N1 119.95(14) . . ?
O1 C7 C6 123.54(14) . . ?
N1 C7 C6 116.51(14) . . ?
O2 C8 N2 121.07(15) . . ?
O2 C8 N1 121.91(14) . . ?
N2 C8 N1 117.02(14) . . ?
O3 C9 N2 120.04(14) . . ?
O3 C9 C6 123.29(14) . . ?
N2 C9 C6 116.67(13) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.95
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 964324'
#######################################################################
#
#                 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_mx118_12

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 N4 O6 S2'
_chemical_formula_sum            'C26 H26 N4 O6 S2'
_chemical_formula_weight         554.63

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 21/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                   5.0394(3)
_cell_length_b                   27.5017(17)
_cell_length_c                   8.9894(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.938(3)
_cell_angle_gamma                90.00
_cell_volume                     1236.74(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4819
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.10

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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 X8 APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11858
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         30.23
_reflns_number_total             3643
_reflns_number_gt                3133
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2012.2 (Bruker AXS, 2012)'
_computing_cell_refinement       'Bruker APEX2 v2012.2 (Bruker AXS, 2012)'
_computing_data_reduction        'Bruker APEX2 v2012.2 (Bruker AXS, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed/POVRay
_computing_publication_material  CIFTAB

_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.
 
 The barbituric group was modeled as disordered with one NEt2 group (N2, 
 C12, C13), two carbonyl groups (C8 O2, and C9, O3) occupying two positions 
 corresponding to a tilting of the six-membered ring by approximately 20 deg 
 with the two Et groups in opposing conformations. The occupances of the 
 two components was refined to 0.65:0.35. Two ISOR restraints were applied 
 to C12' and C13' in the Et group of the minor component to prevent unusual 
 shaped thermal ellipsoids. The highest residual electrondensity peak 
 (0.47 eÅ⁻³) was located within the thiophene ring at the midpoint of 
 the C3-C4 bond.
;

_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)+(0.0455P)²+0.6027P] 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         3643
_refine_ls_number_parameters     236
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.32298(6) 0.551150(11) 0.06339(4) 0.01514(9) Uani 1 1 d . . .
O1 O 1.1400(2) 0.57010(4) 0.53784(11) 0.0230(2) Uani 1 1 d . . .
O2 O 1.4024(6) 0.70488(11) 0.2994(3) 0.0256(6) Uani 0.647(5) 1 d P A 1
O2' O 1.3307(11) 0.71280(19) 0.3377(6) 0.0242(10) Uani 0.353(5) 1 d P A 2
O3 O 0.6877(7) 0.62200(13) 0.0727(4) 0.0213(6) Uani 0.647(5) 1 d P A 1
O3' O 0.6222(13) 0.6297(2) 0.1082(7) 0.0249(11) Uani 0.353(5) 1 d P A 2
N1 N 1.2618(2) 0.63840(4) 0.42517(13) 0.0197(2) Uani 1 1 d . . .
N2 N 1.0537(5) 0.66187(8) 0.1819(3) 0.0159(5) Uani 0.647(5) 1 d P A 1
N2' N 0.9650(9) 0.67232(15) 0.2292(5) 0.0185(10) Uani 0.353(5) 1 d P A 2
C1 C 0.1057(2) 0.50283(5) 0.06088(14) 0.0136(2) Uani 1 1 d . . .
C2 C 0.1631(3) 0.47293(5) 0.18415(15) 0.0168(3) Uani 1 1 d . . .
H2 H 0.0624 0.4448 0.2025 0.020 Uiso 1 1 calc R . .
C3 C 0.3857(3) 0.48882(5) 0.27810(15) 0.0166(2) Uani 1 1 d . . .
H3 H 0.4543 0.4722 0.3671 0.020 Uiso 1 1 calc R . .
C4 C 0.4990(2) 0.53131(5) 0.23011(14) 0.0143(2) Uani 1 1 d . . .
C5 C 0.7280(2) 0.55139(5) 0.31695(14) 0.0148(2) Uani 1 1 d . A .
H5 H 0.7885 0.5317 0.4011 0.018 Uiso 1 1 calc R . .
C6 C 0.8817(3) 0.59181(5) 0.30918(15) 0.0162(2) Uani 1 1 d . . .
C7 C 1.0999(3) 0.59803(5) 0.43220(15) 0.0162(3) Uani 1 1 d . A .
C8 C 1.2515(7) 0.67050(14) 0.3002(4) 0.0167(6) Uani 0.647(5) 1 d P A 1
C8' C 1.1903(14) 0.6773(3) 0.3327(8) 0.0178(12) Uani 0.353(5) 1 d P A 2
C9 C 0.8640(8) 0.62562(16) 0.1785(5) 0.0144(7) Uani 0.647(5) 1 d P A 1
C9' C 0.8051(16) 0.6305(3) 0.2101(9) 0.0175(13) Uani 0.353(5) 1 d P A 2
C10 C 1.4811(3) 0.64549(5) 0.54778(16) 0.0210(3) Uani 1 1 d . A .
H10A H 1.6196 0.6665 0.5118 0.025 Uiso 1 1 calc R . .
H10B H 1.5639 0.6136 0.5757 0.025 Uiso 1 1 calc R . .
C11 C 1.3867(4) 0.66839(8) 0.6850(2) 0.0400(4) Uani 1 1 d . . .
H11A H 1.5389 0.6725 0.7628 0.060 Uiso 1 1 calc R A .
H11B H 1.2527 0.6473 0.7226 0.060 Uiso 1 1 calc R . .
H11C H 1.3072 0.7002 0.6585 0.060 Uiso 1 1 calc R . .
C12 C 1.0453(5) 0.69380(9) 0.0498(3) 0.0221(6) Uani 0.647(5) 1 d P A 1
H12A H 0.9905 0.6744 -0.0415 0.026 Uiso 0.647(5) 1 calc PR A 1
H12B H 1.2272 0.7065 0.0429 0.026 Uiso 0.647(5) 1 calc PR A 1
C12' C 0.8963(9) 0.71354(17) 0.1262(6) 0.0288(13) Uani 0.353(5) 1 d PU A 2
H12C H 0.9586 0.7442 0.1766 0.035 Uiso 0.353(5) 1 calc PR A 2
H12D H 0.6996 0.7155 0.1023 0.035 Uiso 0.353(5) 1 calc PR A 2
C13 C 0.8558(5) 0.73591(10) 0.0550(3) 0.0312(7) Uani 0.647(5) 1 d P A 1
H13A H 0.8577 0.7558 -0.0354 0.047 Uiso 0.647(5) 1 calc PR A 1
H13B H 0.9117 0.7558 0.1438 0.047 Uiso 0.647(5) 1 calc PR A 1
H13C H 0.6746 0.7236 0.0600 0.047 Uiso 0.647(5) 1 calc PR A 1
C13' C 1.0197(12) 0.7085(3) -0.0158(8) 0.0433(16) Uani 0.353(5) 1 d PU A 2
H13D H 0.9691 0.7363 -0.0810 0.065 Uiso 0.353(5) 1 calc PR A 2
H13E H 0.9563 0.6784 -0.0668 0.065 Uiso 0.353(5) 1 calc PR A 2
H13F H 1.2147 0.7073 0.0072 0.065 Uiso 0.353(5) 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.01553(15) 0.01509(16) 0.01385(16) 0.00309(11) -0.00212(11) -0.00234(11)
O1 0.0209(5) 0.0289(5) 0.0178(5) 0.0059(4) -0.0036(4) -0.0032(4)
O2 0.0257(14) 0.0224(11) 0.0273(14) 0.0028(9) -0.0027(9) -0.0088(9)
O2' 0.025(2) 0.022(2) 0.025(2) 0.0018(16) 0.0002(16) -0.0075(16)
O3 0.0222(14) 0.0207(12) 0.0190(14) 0.0044(9) -0.0057(9) -0.0049(9)
O3' 0.025(3) 0.024(2) 0.022(3) 0.0075(19) -0.0100(18) -0.0062(19)
N1 0.0192(5) 0.0179(6) 0.0198(6) 0.0003(4) -0.0063(4) -0.0017(4)
N2 0.0148(10) 0.0162(9) 0.0159(10) 0.0024(7) -0.0007(8) -0.0013(7)
N2' 0.0193(19) 0.0186(18) 0.0167(19) 0.0059(14) -0.0012(15) -0.0053(15)
C1 0.0125(5) 0.0155(6) 0.0128(6) -0.0010(4) 0.0024(4) -0.0009(4)
C2 0.0171(6) 0.0190(6) 0.0143(6) 0.0032(5) 0.0014(5) -0.0026(5)
C3 0.0173(6) 0.0190(6) 0.0132(6) 0.0041(5) 0.0006(5) -0.0009(5)
C4 0.0139(5) 0.0163(6) 0.0125(6) 0.0002(4) 0.0003(4) 0.0006(4)
C5 0.0148(6) 0.0176(6) 0.0120(6) 0.0006(5) 0.0013(4) 0.0017(4)
C6 0.0162(6) 0.0163(6) 0.0150(6) -0.0005(5) -0.0025(5) 0.0006(5)
C7 0.0143(6) 0.0185(6) 0.0155(6) -0.0017(5) -0.0001(5) 0.0016(4)
C8 0.0154(16) 0.0160(13) 0.0180(17) -0.0012(11) -0.0005(10) 0.0019(10)
C8' 0.015(3) 0.020(3) 0.019(3) -0.005(2) 0.0028(19) -0.001(2)
C9 0.0139(18) 0.0165(12) 0.0127(17) 0.0024(11) 0.0011(10) 0.0000(11)
C9' 0.014(3) 0.020(3) 0.020(3) 0.000(2) 0.005(2) -0.008(2)
C10 0.0178(6) 0.0214(7) 0.0217(7) -0.0038(5) -0.0057(5) 0.0001(5)
C11 0.0356(9) 0.0495(11) 0.0331(9) -0.0220(8) -0.0036(7) 0.0049(8)
C12 0.0211(11) 0.0231(12) 0.0209(13) 0.0097(10) -0.0022(9) -0.0043(8)
C12' 0.027(2) 0.022(2) 0.035(3) 0.0138(19) -0.0081(18) -0.0096(16)
C13 0.0237(12) 0.0266(14) 0.0418(17) 0.0151(12) -0.0023(11) -0.0005(9)
C13' 0.041(3) 0.057(4) 0.031(3) 0.012(3) -0.003(2) -0.022(3)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7204(13) . ?
S1 C4 1.7348(13) . ?
O1 C7 1.2191(16) . ?
O2 C8 1.214(5) . ?
O2' C8' 1.204(9) . ?
O3 C9 1.224(6) . ?
O3' C9' 1.219(11) . ?
N1 C8' 1.376(8) . ?
N1 C7 1.3840(17) . ?
N1 C8 1.425(4) . ?
N1 C10 1.4761(17) . ?
N2 C9 1.379(5) . ?
N2 C8 1.387(4) . ?
N2 C12 1.473(4) . ?
N2' C8' 1.384(8) . ?
N2' C9' 1.404(9) . ?
N2' C12' 1.478(6) . ?
C1 C2 1.3821(18) . ?
C1 C1 1.440(2) 3_565 ?
C2 C3 1.3905(18) . ?
C3 C4 1.3917(18) . ?
C4 C5 1.4243(18) . ?
C5 C6 1.3615(18) . ?
C6 C9' 1.410(9) . ?
C6 C7 1.4722(18) . ?
C6 C9 1.493(5) . ?
C10 C11 1.512(2) . ?
C12 C13 1.505(4) . ?
C12' C13' 1.492(8) . ?

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 S1 C4 91.52(6) . . ?
C8' N1 C7 122.6(3) . . ?
C7 N1 C8 124.56(19) . . ?
C8' N1 C10 117.8(3) . . ?
C7 N1 C10 117.64(11) . . ?
C8 N1 C10 117.39(19) . . ?
C9 N2 C8 124.9(3) . . ?
C9 N2 C12 117.4(2) . . ?
C8 N2 C12 117.6(2) . . ?
C8' N2' C9' 125.1(6) . . ?
C8' N2' C12' 117.1(4) . . ?
C9' N2' C12' 117.7(5) . . ?
C2 C1 C1 127.52(15) . 3_565 ?
C2 C1 S1 112.19(9) . . ?
C1 C1 S1 120.29(13) 3_565 . ?
C1 C2 C3 112.05(12) . . ?
C2 C3 C4 114.00(12) . . ?
C3 C4 C5 119.43(12) . . ?
C3 C4 S1 110.23(9) . . ?
C5 C4 S1 130.35(10) . . ?
C6 C5 C4 135.79(12) . . ?
C5 C6 C9' 122.3(4) . . ?
C5 C6 C7 115.74(12) . . ?
C9' C6 C7 120.6(4) . . ?
C5 C6 C9 124.7(2) . . ?
C7 C6 C9 119.2(2) . . ?
O1 C7 N1 119.86(12) . . ?
O1 C7 C6 123.40(12) . . ?
N1 C7 C6 116.74(12) . . ?
O2 C8 N2 121.4(3) . . ?
O2 C8 N1 121.6(3) . . ?
N2 C8 N1 116.9(3) . . ?
O2' C8' N1 119.9(6) . . ?
O2' C8' N2' 122.4(7) . . ?
O3 C9 N2 120.8(4) . . ?
O3 C9 C6 122.0(4) . . ?
N2 C9 C6 117.2(3) . . ?
O3' C9' N2' 118.5(8) . . ?
O3' C9' C6 125.8(7) . . ?
N1 C10 C11 112.54(13) . . ?
N2 C12 C13 113.0(3) . . ?
N2' C12' C13' 111.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 964325'
