# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# 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_test
_audit_creation_date             2014-05-05
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 N2 O4 S'
_chemical_formula_sum            'C20 H0 N6 O0.13 S'
_chemical_formula_weight         358.32
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.0878(14)
_cell_length_b                   12.7641(16)
_cell_length_c                   28.139(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3623.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19935
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.45
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2721
_reflns_number_total             4112
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.7138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1197
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.08092(5) 0.54348(4) 0.566710(18) 0.03774(16) Uani 1 1 d . . .
O2 O -0.11964(14) 0.43742(12) 0.57378(5) 0.0477(4) Uani 1 1 d . . .
O1 O -0.12654(14) 0.59720(13) 0.52544(5) 0.0486(4) Uani 1 1 d . . .
O3 O 0.14420(15) 0.37828(12) 0.59357(6) 0.0508(4) Uani 1 1 d . . .
O4 O 0.10942(15) 0.71658(12) 0.53744(6) 0.0533(4) Uani 1 1 d . . .
N2 N 0.08540(15) 0.54452(13) 0.56465(6) 0.0343(4) Uani 1 1 d . . .
N1 N -0.1276(2) 0.69447(15) 0.78736(6) 0.0494(5) Uani 1 1 d . . .
C12 C -0.11668(19) 0.62080(16) 0.61708(7) 0.0359(5) Uani 1 1 d . . .
C14 C 0.1748(2) 0.46124(16) 0.57738(7) 0.0349(5) Uani 1 1 d . . .
C16 C 0.29921(19) 0.60352(15) 0.54990(7) 0.0333(4) Uani 1 1 d . . .
C13 C 0.1583(2) 0.63472(16) 0.54834(7) 0.0358(5) Uani 1 1 d . . .
C15 C 0.30860(19) 0.50272(15) 0.56734(7) 0.0336(4) Uani 1 1 d . . .
C7 C -0.09532(19) 0.58320(16) 0.66441(7) 0.0351(5) Uani 1 1 d . . .
C8 C -0.12282(19) 0.65447(16) 0.70233(7) 0.0357(5) Uani 1 1 d . . .
C17 C 0.4101(2) 0.66112(17) 0.53795(7) 0.0415(5) Uani 1 1 d . . .
H17 H 0.4036 0.7291 0.5262 0.050 Uiso 1 1 calc R . .
C20 C 0.4292(2) 0.45482(17) 0.57401(8) 0.0436(5) Uani 1 1 d . . .
H20 H 0.4354 0.3871 0.5860 0.052 Uiso 1 1 calc R . .
C9 C -0.1651(2) 0.75696(18) 0.69140(8) 0.0454(5) Uani 1 1 d . . .
H9 H -0.1801 0.8039 0.7161 0.054 Uiso 1 1 calc R . .
C6 C -0.0458(2) 0.48268(17) 0.67540(8) 0.0467(6) Uani 1 1 d . . .
H6 H -0.0279 0.4353 0.6511 0.056 Uiso 1 1 calc R . .
C11 C -0.1604(2) 0.72094(17) 0.60839(8) 0.0438(5) Uani 1 1 d . . .
H11 H -0.1738 0.7431 0.5773 0.053 Uiso 1 1 calc R . .
C10 C -0.1848(2) 0.78949(18) 0.64595(8) 0.0492(6) Uani 1 1 d . . .
H10 H -0.2143 0.8572 0.6399 0.059 Uiso 1 1 calc R . .
C3 C -0.1014(2) 0.62165(17) 0.75051(7) 0.0431(5) Uani 1 1 d . . .
C19 C 0.5414(2) 0.51212(19) 0.56212(8) 0.0489(6) Uani 1 1 d . . .
H19 H 0.6246 0.4822 0.5663 0.059 Uiso 1 1 calc R . .
C18 C 0.5321(2) 0.61225(19) 0.54433(8) 0.0469(6) Uani 1 1 d . . .
H18 H 0.6092 0.6481 0.5364 0.056 Uiso 1 1 calc R . .
C5 C -0.0243(3) 0.45490(19) 0.72125(9) 0.0603(7) Uani 1 1 d . . .
H5 H 0.0088 0.3885 0.7279 0.072 Uiso 1 1 calc R . .
C4 C -0.0506(3) 0.52363(19) 0.75887(8) 0.0591(7) Uani 1 1 d . . .
H4 H -0.0334 0.5026 0.7899 0.071 Uiso 1 1 calc R . .
C1 C -0.2678(3) 0.7091(3) 0.79788(11) 0.0865(10) Uani 1 1 d . . .
H1A H -0.3160 0.7178 0.7687 0.130 Uiso 1 1 calc R . .
H1B H -0.2789 0.7702 0.8174 0.130 Uiso 1 1 calc R . .
H1C H -0.3008 0.6488 0.8145 0.130 Uiso 1 1 calc R . .
C2 C -0.0506(3) 0.6789(2) 0.83084(8) 0.0686(8) Uani 1 1 d . . .
H2A H -0.0834 0.6186 0.8475 0.103 Uiso 1 1 calc R . .
H2B H -0.0587 0.7396 0.8508 0.103 Uiso 1 1 calc R . .
H2C H 0.0410 0.6682 0.8228 0.103 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 O2 1.4229(16) . ?
S1 O1 1.4249(15) . ?
S1 N2 1.6789(16) . ?
S1 C12 1.764(2) . ?
O3 C14 1.193(2) . ?
O4 C13 1.195(2) . ?
N2 C14 1.440(3) . ?
N2 C13 1.441(2) . ?
N1 C3 1.417(3) . ?
N1 C1 1.457(3) . ?
N1 C2 1.463(3) . ?
C12 C7 1.432(3) . ?
C12 C11 1.374(3) . ?
C14 C15 1.477(3) . ?
C16 C13 1.477(3) . ?
C16 C15 1.380(3) . ?
C16 C17 1.380(3) . ?
C15 C20 1.375(3) . ?
C7 C8 1.429(3) . ?
C7 C6 1.411(3) . ?
C8 C9 1.410(3) . ?
C8 C3 1.435(3) . ?
C17 C18 1.391(3) . ?
C20 C19 1.388(3) . ?
C9 C10 1.359(3) . ?
C6 C5 1.356(3) . ?
C11 C10 1.394(3) . ?
C3 C4 1.372(3) . ?
C19 C18 1.376(3) . ?
C5 C4 1.400(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
O2 S1 O1 118.89(9) . . ?
O2 S1 N2 106.66(9) . . ?
O2 S1 C12 111.33(9) . . ?
O1 S1 N2 106.90(9) . . ?
O1 S1 C12 108.63(10) . . ?
N2 S1 C12 103.16(9) . . ?
C14 N2 S1 127.72(14) . . ?
C14 N2 C13 110.46(15) . . ?
C13 N2 S1 121.82(13) . . ?
C3 N1 C1 114.4(2) . . ?
C3 N1 C2 115.06(19) . . ?
C1 N1 C2 111.3(2) . . ?
C7 C12 S1 121.93(15) . . ?
C11 C12 S1 116.30(16) . . ?
C11 C12 C7 121.71(19) . . ?
O3 C14 N2 126.01(19) . . ?
O3 C14 C15 128.9(2) . . ?
N2 C14 C15 105.08(16) . . ?
C15 C16 C13 109.14(17) . . ?
C15 C16 C17 121.83(19) . . ?
C17 C16 C13 129.00(19) . . ?
O4 C13 N2 124.73(18) . . ?
O4 C13 C16 129.81(19) . . ?
N2 C13 C16 105.44(16) . . ?
C16 C15 C14 109.85(17) . . ?
C20 C15 C14 128.55(19) . . ?
C20 C15 C16 121.59(19) . . ?
C8 C7 C12 116.85(18) . . ?
C6 C7 C12 124.18(19) . . ?
C6 C7 C8 118.94(18) . . ?
C7 C8 C3 119.34(18) . . ?
C9 C8 C7 119.11(19) . . ?
C9 C8 C3 121.50(19) . . ?
C16 C17 C18 116.5(2) . . ?
C15 C20 C19 117.0(2) . . ?
C10 C9 C8 122.2(2) . . ?
C5 C6 C7 120.2(2) . . ?
C12 C11 C10 120.4(2) . . ?
C9 C10 C11 119.7(2) . . ?
N1 C3 C8 118.12(19) . . ?
C4 C3 N1 122.8(2) . . ?
C4 C3 C8 119.0(2) . . ?
C18 C19 C20 121.4(2) . . ?
C19 C18 C17 121.6(2) . . ?
C6 C5 C4 121.7(2) . . ?
C3 C4 C5 120.8(2) . . ?

_database_code_depnum_ccdc_archive 'CCDC 1014564'
