# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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#
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#                                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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_PB_9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H18 N3 O), S O4, 3(H2 O)'
_chemical_formula_sum            'C42 H42 N6 O9 S'
_chemical_formula_weight         806.88

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   'C 2/c'

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

_cell_length_a                   16.3414(8)
_cell_length_b                   17.0145(9)
_cell_length_c                   16.3578(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.819(3)
_cell_angle_gamma                90.00
_cell_volume                     3984.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2266
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      19.56

_exptl_crystal_description       block
_exptl_crystal_colour            'deep yellow'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21422
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         21.51
_reflns_number_total             2290
_reflns_number_gt                1674
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-2 (Bruker, 2004)'
_computing_cell_refinement       'Bruker APEX-2 (Bruker, 2004)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 1.80.05 (Farrugia, 1999)'

_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. 

 Hydrogen atoms at O2w at half occupancy not located
;

_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)+(0.0974P)²+3.5800P] 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         2290
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1513
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.7599(2) 0.11000(19) 0.6386(2) 0.0580(9) Uani 1 1 d . . .
H1N H 0.813(3) 0.084(2) 0.649(3) 0.070 Uiso 1 1 d . . .
N2 N 0.6359(2) 0.18370(17) 0.5674(2) 0.0537(9) Uani 1 1 d . . .
N3 N 0.5796(2) 0.2394(2) 0.4183(3) 0.0639(10) Uani 1 1 d . . .
H3N H 0.547(3) 0.271(3) 0.377(3) 0.077 Uiso 1 1 d . . .
O1 O 0.52661(19) 0.07188(15) 0.4188(2) 0.0705(9) Uani 1 1 d . . .
C5 C 0.3092(3) 0.1736(3) 0.4423(3) 0.0768(13) Uani 1 1 d . . .
H5 H 0.2609 0.1975 0.4477 0.092 Uiso 1 1 calc R . .
C6 C 0.3926(3) 0.2130(3) 0.4691(3) 0.0685(12) Uani 1 1 d . . .
H6 H 0.3998 0.2638 0.4926 0.082 Uiso 1 1 calc R . .
C4 C 0.2991(3) 0.0989(3) 0.4077(3) 0.0782(14) Uani 1 1 d . . .
H4 H 0.2436 0.0719 0.3901 0.094 Uiso 1 1 calc R . .
C8 C 0.5564(3) 0.2242(2) 0.4915(3) 0.0595(11) Uani 1 1 d . . .
H8 H 0.5499 0.2752 0.5157 0.071 Uiso 1 1 calc R . .
C7 C 0.4653(3) 0.1784(2) 0.4617(3) 0.0557(10) Uani 1 1 d . . .
C20 C 0.6024(3) 0.1987(3) 0.7031(3) 0.0733(13) Uani 1 1 d . . .
H20 H 0.5502 0.2310 0.6736 0.088 Uiso 1 1 calc R . .
C19 C 0.6374(4) 0.1744(3) 0.7948(4) 0.0860(15) Uani 1 1 d . . .
H19 H 0.6075 0.1909 0.8279 0.103 Uiso 1 1 calc R . .
C3 C 0.3697(3) 0.0632(3) 0.3985(3) 0.0688(12) Uani 1 1 d . . .
H3 H 0.3616 0.0125 0.3745 0.083 Uiso 1 1 calc R . .
C21 C 0.6505(3) 0.1716(2) 0.6582(3) 0.0578(11) Uani 1 1 d . . .
C2 C 0.4526(3) 0.1025(2) 0.4249(3) 0.0583(11) Uani 1 1 d . . .
C9 C 0.6431(3) 0.1984(2) 0.4039(3) 0.0582(11) Uani 1 1 d . . .
C10 C 0.6488(3) 0.2086(3) 0.3224(3) 0.0709(12) Uani 1 1 d . . .
H10 H 0.6078 0.2425 0.2762 0.085 Uiso 1 1 calc R . .
C18 C 0.7151(4) 0.1266(3) 0.8388(3) 0.0854(14) Uani 1 1 d . . .
H18 H 0.7350 0.1110 0.9000 0.102 Uiso 1 1 calc R . .
C15 C 0.7031(3) 0.1454(2) 0.5582(3) 0.0530(10) Uani 1 1 d . . .
C16 C 0.7293(3) 0.1253(2) 0.7033(3) 0.0568(10) Uani 1 1 d . . .
C14 C 0.7083(3) 0.1482(2) 0.4733(3) 0.0539(10) Uani 1 1 d . . .
C17 C 0.7634(3) 0.1015(3) 0.7949(3) 0.0729(12) Uani 1 1 d . . .
H17 H 0.8164 0.0701 0.8249 0.087 Uiso 1 1 calc R . .
C11 C 0.7148(4) 0.1688(3) 0.3100(3) 0.0779(14) Uani 1 1 d . . .
H11 H 0.7175 0.1760 0.2550 0.094 Uiso 1 1 calc R . .
C1 C 0.5138(4) 0.0025(3) 0.3665(3) 0.0901(15) Uani 1 1 d . . .
H1A H 0.5061 -0.0414 0.3991 0.135 Uiso 1 1 calc R . .
H1B H 0.5675 -0.0061 0.3583 0.135 Uiso 1 1 calc R . .
H1C H 0.4593 0.0077 0.3066 0.135 Uiso 1 1 calc R . .
C13 C 0.7753(3) 0.1075(2) 0.4592(3) 0.0636(11) Uani 1 1 d . . .
H13 H 0.8174 0.0739 0.5050 0.076 Uiso 1 1 calc R . .
C12 C 0.7781(3) 0.1177(3) 0.3775(4) 0.0771(13) Uani 1 1 d . . .
H12 H 0.8217 0.0907 0.3671 0.093 Uiso 1 1 calc R . .
S1 S 0.5000 0.42343(9) 0.2500 0.0734(6) Uani 1 2 d S . .
O4 O 0.4792(2) 0.3735(2) 0.3106(3) 0.1005(12) Uani 1 1 d . . .
O3 O 0.58144(18) 0.47318(17) 0.3064(2) 0.0813(10) Uani 1 1 d . . .
O1W O 0.5512(6) 0.6211(4) 0.3719(7) 0.283(5) Uani 1 1 d . . .
H1W H 0.5647 0.5719 0.3496 0.424 Uiso 1 1 d R . .
H2W H 0.5404 0.6038 0.4224 0.424 Uiso 1 1 d R . .
O2W O 0.5183(6) 0.5690(7) 0.5251(6) 0.155(4) Uani 0.50 1 d P . .


_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 C15 1.333(5) . ?
N1 C16 1.397(5) . ?
N1 H1N 0.91(4) . ?
N2 C15 1.347(5) . ?
N2 C21 1.402(5) . ?
N2 C8 1.465(5) . ?
N3 C9 1.363(5) . ?
N3 C8 1.443(5) . ?
N3 H3N 0.82(4) . ?
O1 C2 1.365(5) . ?
O1 C1 1.414(5) . ?
C5 C4 1.368(6) . ?
C5 C6 1.388(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(5) . ?
C6 H6 0.9300 . ?
C4 C3 1.375(6) . ?
C4 H4 0.9300 . ?
C8 C7 1.537(5) . ?
C8 H8 0.9800 . ?
C7 C2 1.397(5) . ?
C20 C19 1.386(7) . ?
C20 C21 1.387(6) . ?
C20 H20 0.9300 . ?
C19 C18 1.383(7) . ?
C19 H19 0.9300 . ?
C3 C2 1.381(5) . ?
C3 H3 0.9300 . ?
C21 C16 1.381(5) . ?
C9 C10 1.391(6) . ?
C9 C14 1.410(5) . ?
C10 C11 1.368(6) . ?
C10 H10 0.9300 . ?
C18 C17 1.367(6) . ?
C18 H18 0.9300 . ?
C15 C14 1.432(5) . ?
C16 C17 1.384(6) . ?
C14 C13 1.405(5) . ?
C17 H17 0.9300 . ?
C11 C12 1.394(7) . ?
C11 H11 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C13 C12 1.370(6) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
S1 O4 1.465(3) 2_655 ?
S1 O4 1.465(3) . ?
S1 O3 1.468(3) 2_655 ?
S1 O3 1.468(3) . ?
O1W H1W 0.9790 . ?
O1W H2W 0.9711 . ?

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
C15 N1 C16 109.2(3) . . ?
C15 N1 H1N 123(3) . . ?
C16 N1 H1N 127(3) . . ?
C15 N2 C21 108.4(3) . . ?
C15 N2 C8 124.8(3) . . ?
C21 N2 C8 126.5(3) . . ?
C9 N3 C8 125.4(3) . . ?
C9 N3 H3N 116(3) . . ?
C8 N3 H3N 118(3) . . ?
C2 O1 C1 119.1(3) . . ?
C4 C5 C6 118.9(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 121.5(4) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N3 C8 N2 107.9(3) . . ?
N3 C8 C7 115.4(3) . . ?
N2 C8 C7 110.9(3) . . ?
N3 C8 H8 107.4 . . ?
N2 C8 H8 107.4 . . ?
C7 C8 H8 107.4 . . ?
C6 C7 C2 118.4(4) . . ?
C6 C7 C8 119.9(4) . . ?
C2 C7 C8 121.7(4) . . ?
C19 C20 C21 115.5(4) . . ?
C19 C20 H20 122.3 . . ?
C21 C20 H20 122.3 . . ?
C18 C19 C20 122.4(4) . . ?
C18 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C16 C21 C20 121.8(4) . . ?
C16 C21 N2 106.7(3) . . ?
C20 C21 N2 131.4(4) . . ?
O1 C2 C3 124.2(4) . . ?
O1 C2 C7 115.6(3) . . ?
C3 C2 C7 120.2(4) . . ?
N3 C9 C10 120.8(4) . . ?
N3 C9 C14 120.8(4) . . ?
C10 C9 C14 118.3(4) . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C17 C18 C19 121.9(5) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
N1 C15 N2 109.0(4) . . ?
N1 C15 C14 129.3(4) . . ?
N2 C15 C14 121.7(4) . . ?
C21 C16 C17 122.0(4) . . ?
C21 C16 N1 106.6(4) . . ?
C17 C16 N1 131.4(4) . . ?
C13 C14 C9 120.8(4) . . ?
C13 C14 C15 123.9(4) . . ?
C9 C14 C15 115.3(4) . . ?
C18 C17 C16 116.4(5) . . ?
C18 C17 H17 121.8 . . ?
C16 C17 H17 121.8 . . ?
C10 C11 C12 121.9(4) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
O4 S1 O4 109.1(3) 2_655 . ?
O4 S1 O3 110.2(2) 2_655 2_655 ?
O4 S1 O3 108.90(17) . 2_655 ?
O4 S1 O3 108.91(17) 2_655 . ?
O4 S1 O3 110.2(2) . . ?
O3 S1 O3 109.6(2) 2_655 . ?
H1W O1W H2W 103.0 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        21.51
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 1007155'
