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

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#
#                 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.
#
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#  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_d1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N4 O7 S1'
_chemical_formula_sum            'C60 H64 N16 O28 S4'
_chemical_formula_weight         1585.51

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   P21/C

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                   19.299
_cell_length_b                   6.620
_cell_length_c                   14.534
_cell_angle_alpha                90.00
_cell_angle_beta                 102.77
_cell_angle_gamma                90.00
_cell_volume                     1811.0
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.2417
_cell_measurement_theta_max      29.1619

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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            7741
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.1004
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         29.23
_reflns_number_total             4127
_reflns_number_gt                1809
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0535P)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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4127
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1691
_refine_ls_R_factor_gt           0.0694
_refine_ls_wR_factor_ref         0.1759
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
O1 O 0.38690(14) 0.4189(4) 0.37522(16) 0.0599(8) Uani 1 1 d . . .
H2 H 0.4222 0.4177 0.3524 0.090 Uiso 1 1 calc R . .
O2 O 0.13833(13) 0.4265(4) 0.28968(17) 0.0633(8) Uani 1 1 d . . .
H3 H 0.1052 0.4270 0.2433 0.095 Uiso 1 1 calc R . .
O3 O 0.57006(15) 0.4234(4) 0.04150(17) 0.0642(8) Uani 1 1 d . . .
O4 O 0.68313(15) 0.4339(4) 0.05690(17) 0.0697(9) Uani 1 1 d . . .
O5 O 0.84449(15) 0.4192(4) 0.3501(2) 0.0687(8) Uani 1 1 d . . .
O6 O 0.80823(16) 0.4253(5) 0.4798(2) 0.0837(10) Uani 1 1 d . . .
N1 N 0.45879(15) 0.4180(4) 0.23493(19) 0.0370(7) Uani 1 1 d . . .
N2 N 0.51464(14) 0.4199(4) 0.18922(19) 0.0390(7) Uani 1 1 d . . .
H1 H 0.5058 0.4204 0.1286 0.047 Uiso 1 1 d R . .
N3 N 0.63097(18) 0.4273(4) 0.0917(2) 0.0470(8) Uani 1 1 d . . .
N4 N 0.79735(18) 0.4203(4) 0.3931(3) 0.0521(9) Uani 1 1 d . . .
C7 C 0.39685(19) 0.4166(4) 0.1786(2) 0.0377(8) Uani 1 1 d . . .
H4 H 0.3946 0.4156 0.1140 0.045 Uiso 1 1 calc R . .
C1 C 0.33142(17) 0.4165(4) 0.2094(2) 0.0327(8) Uani 1 1 d . . .
C2 C 0.32747(19) 0.4188(5) 0.3048(2) 0.0374(8) Uani 1 1 d . . .
C3 C 0.2628(2) 0.4210(5) 0.3300(2) 0.0446(9) Uani 1 1 d . . .
H5 H 0.2611 0.4219 0.3934 0.054 Uiso 1 1 calc R . .
C4 C 0.2002(2) 0.4219(5) 0.2616(3) 0.0437(9) Uani 1 1 d . . .
C5 C 0.20264(18) 0.4180(5) 0.1663(2) 0.0410(9) Uani 1 1 d . . .
H6 H 0.1608 0.4168 0.1199 0.049 Uiso 1 1 calc R . .
C6 C 0.26698(19) 0.4159(4) 0.1418(2) 0.0387(8) Uani 1 1 d . . .
H7 H 0.2682 0.4140 0.0782 0.046 Uiso 1 1 calc R . .
C8 C 0.58249(18) 0.4191(4) 0.2376(2) 0.0338(8) Uani 1 1 d . . .
C9 C 0.64075(18) 0.4223(5) 0.1929(2) 0.0343(8) Uani 1 1 d . . .
C10 C 0.71029(18) 0.4214(4) 0.2439(2) 0.0364(8) Uani 1 1 d . . .
H10 H 0.7476 0.4224 0.2129 0.044 Uiso 1 1 calc R . .
C11 C 0.72360(19) 0.4190(5) 0.3402(2) 0.0372(8) Uani 1 1 d . . .
C12 C 0.6683(2) 0.4148(5) 0.3873(2) 0.0420(9) Uani 1 1 d . . .
H9 H 0.6783 0.4121 0.4529 0.050 Uiso 1 1 calc R . .
C13 C 0.59991(19) 0.4146(4) 0.3380(2) 0.0382(8) Uani 1 1 d . . .
H8 H 0.5635 0.4115 0.3706 0.046 Uiso 1 1 calc R . .
S1 S 0.02586(6) 0.09925(19) 0.34282(8) 0.0708(4) Uani 1 1 d . . .
O7 O -0.03340(15) -0.0387(4) 0.35666(19) 0.0777(9) Uani 1 1 d . . .
C14 C 0.1043(3) -0.0308(7) 0.3932(4) 0.1007(17) Uani 1 1 d . . .
H12 H 0.1089 -0.1468 0.3553 0.151 Uiso 1 1 calc R . .
H13 H 0.1026 -0.0738 0.4558 0.151 Uiso 1 1 calc R . .
H11 H 0.1443 0.0569 0.3961 0.151 Uiso 1 1 calc R . .
C15 C 0.0303(2) 0.2912(6) 0.4282(3) 0.0825(14) Uani 1 1 d . . .
H14 H 0.0349 0.2312 0.4894 0.124 Uiso 1 1 calc R . .
H15 H -0.0122 0.3711 0.4135 0.124 Uiso 1 1 calc R . .
H16 H 0.0707 0.3758 0.4282 0.124 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
O1 C2 1.358(4) . ?
O1 H2 0.8200 . ?
O2 C4 1.345(4) . ?
O2 H3 0.8200 . ?
O3 N3 1.239(4) . ?
O4 N3 1.223(4) . ?
O5 N4 1.212(4) . ?
O6 N4 1.230(4) . ?
N1 C7 1.291(4) . ?
N1 N2 1.386(4) . ?
N2 C8 1.342(4) . ?
N2 H1 0.8596 . ?
N3 C9 1.442(4) . ?
N4 C11 1.461(4) . ?
C7 C1 1.430(4) . ?
C7 H4 0.9300 . ?
C1 C6 1.404(4) . ?
C1 C2 1.405(4) . ?
C2 C3 1.377(5) . ?
C3 C4 1.384(5) . ?
C3 H5 0.9300 . ?
C4 C5 1.397(4) . ?
C5 C6 1.365(4) . ?
C5 H6 0.9300 . ?
C6 H7 0.9300 . ?
C8 C9 1.417(4) . ?
C8 C13 1.424(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.366(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(5) . ?
C12 C13 1.356(4) . ?
C12 H9 0.9300 . ?
C13 H8 0.9300 . ?
S1 O7 1.511(3) . ?
S1 C14 1.755(5) . ?
S1 C15 1.765(4) . ?
C14 H12 0.9600 . ?
C14 H13 0.9600 . ?
C14 H11 0.9600 . ?
C15 H14 0.9600 . ?
C15 H15 0.9600 . ?
C15 H16 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 O1 H2 109.5 . . ?
C4 O2 H3 109.5 . . ?
C7 N1 N2 113.9(3) . . ?
C8 N2 N1 121.4(3) . . ?
C8 N2 H1 119.1 . . ?
N1 N2 H1 119.5 . . ?
O4 N3 O3 121.1(3) . . ?
O4 N3 C9 119.3(3) . . ?
O3 N3 C9 119.6(3) . . ?
O5 N4 O6 123.4(3) . . ?
O5 N4 C11 118.9(3) . . ?
O6 N4 C11 117.7(3) . . ?
N1 C7 C1 124.0(3) . . ?
N1 C7 H4 118.0 . . ?
C1 C7 H4 118.0 . . ?
C6 C1 C2 117.2(3) . . ?
C6 C1 C7 119.2(3) . . ?
C2 C1 C7 123.6(3) . . ?
O1 C2 C3 117.7(3) . . ?
O1 C2 C1 121.5(3) . . ?
C3 C2 C1 120.8(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H5 119.7 . . ?
C4 C3 H5 119.7 . . ?
O2 C4 C3 118.3(3) . . ?
O2 C4 C5 121.9(3) . . ?
C3 C4 C5 119.7(3) . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H6 120.3 . . ?
C4 C5 H6 120.3 . . ?
C5 C6 C1 122.2(3) . . ?
C5 C6 H7 118.9 . . ?
C1 C6 H7 118.9 . . ?
N2 C8 C9 122.8(3) . . ?
N2 C8 C13 121.2(3) . . ?
C9 C8 C13 116.0(3) . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 N3 116.1(3) . . ?
C8 C9 N3 122.0(3) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 N4 118.7(3) . . ?
C12 C11 N4 120.3(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H9 119.9 . . ?
C11 C12 H9 119.9 . . ?
C12 C13 C8 121.5(3) . . ?
C12 C13 H8 119.2 . . ?
C8 C13 H8 119.2 . . ?
O7 S1 C14 104.8(2) . . ?
O7 S1 C15 105.2(2) . . ?
C14 S1 C15 99.0(2) . . ?
S1 C14 H12 109.5 . . ?
S1 C14 H13 109.5 . . ?
H12 C14 H13 109.5 . . ?
S1 C14 H11 109.5 . . ?
H12 C14 H11 109.5 . . ?
H13 C14 H11 109.5 . . ?
S1 C15 H14 109.5 . . ?
S1 C15 H15 109.5 . . ?
H14 C15 H15 109.5 . . ?
S1 C15 H16 109.5 . . ?
H14 C15 H16 109.5 . . ?
H15 C15 H16 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
C7 N1 N2 C8 -179.2(3) . . . . ?
N2 N1 C7 C1 -179.4(3) . . . . ?
N1 C7 C1 C6 179.7(3) . . . . ?
N1 C7 C1 C2 0.3(5) . . . . ?
C6 C1 C2 O1 179.8(3) . . . . ?
C7 C1 C2 O1 -0.8(5) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C7 C1 C2 C3 179.2(3) . . . . ?
O1 C2 C3 C4 179.7(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 O2 -179.3(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
O2 C4 C5 C6 179.2(3) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C7 C1 C6 C5 -179.3(3) . . . . ?
N1 N2 C8 C9 -179.6(3) . . . . ?
N1 N2 C8 C13 0.5(4) . . . . ?
N2 C8 C9 C10 -180.0(3) . . . . ?
C13 C8 C9 C10 -0.1(5) . . . . ?
N2 C8 C9 N3 0.2(5) . . . . ?
C13 C8 C9 N3 -179.9(3) . . . . ?
O4 N3 C9 C10 -1.3(5) . . . . ?
O3 N3 C9 C10 178.3(3) . . . . ?
O4 N3 C9 C8 178.6(3) . . . . ?
O3 N3 C9 C8 -1.9(5) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
N3 C9 C10 C11 179.3(3) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C9 C10 C11 N4 -179.3(3) . . . . ?
O5 N4 C11 C10 -1.5(5) . . . . ?
O6 N4 C11 C10 177.5(3) . . . . ?
O5 N4 C11 C12 178.3(3) . . . . ?
O6 N4 C11 C12 -2.7(5) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
N4 C11 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C8 -0.1(5) . . . . ?
N2 C8 C13 C12 -179.7(3) . . . . ?
C9 C8 C13 C12 0.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.841
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 978704'
