# 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.
#
#  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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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9.75 H9.75 N9.75 O9.75'
_chemical_formula_weight         425.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   7.917(5)
_cell_length_b                   12.258(5)
_cell_length_c                   20.049(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.658(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1932.6(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1880
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      21.98

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             858
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_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 scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9806
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3417
_reflns_number_gt                2137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0651P)²+3.8299P] 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         3417
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0802
_refine_ls_wR_factor_ref         0.2164
_refine_ls_wR_factor_gt          0.1862
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.231
_refine_ls_shift/su_max          0.000
_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
O7 O 1.0506(4) 0.0638(3) 0.14802(16) 0.0602(10) Uani 1 1 d . . .
C3 C 1.0799(6) 0.1732(4) 0.0512(2) 0.0457(11) Uani 1 1 d . . .
C6 C 0.9960(5) 0.0957(4) 0.0908(2) 0.0438(11) Uani 1 1 d . . .
C5 C 0.8382(6) 0.0573(4) 0.0537(2) 0.0452(11) Uani 1 1 d . . .
C4 C 0.7820(6) 0.0841(4) -0.0108(2) 0.0467(11) Uani 1 1 d . . .
H4 H 0.6829 0.0533 -0.0323 0.056 Uiso 1 1 calc R . .
O2 O 0.6900(5) 0.1434(3) -0.14077(18) 0.0721(11) Uani 1 1 d . . .
N1 N 0.8188(6) 0.1861(4) -0.1130(2) 0.0573(11) Uani 1 1 d . . .
C1 C 0.8748(6) 0.1581(4) -0.0441(2) 0.0456(11) Uani 1 1 d . . .
C2 C 1.0216(6) 0.2042(4) -0.0124(2) 0.0478(11) Uani 1 1 d . . .
H2 H 1.0803 0.2561 -0.0345 0.057 Uiso 1 1 calc R . .
N3 N 0.7318(5) -0.0176(4) 0.0868(2) 0.0648(13) Uani 1 1 d . . .
O1 O 0.9046(6) 0.2520(4) -0.14111(19) 0.0802(12) Uani 1 1 d . . .
N4 N 0.3223(7) 0.0783(5) 0.2474(2) 0.0738(15) Uani 1 1 d . . .
H4A H 0.2643 0.0697 0.2088 0.089 Uiso 1 1 calc R . .
N2 N 1.2379(6) 0.2230(4) 0.0795(2) 0.0721(14) Uani 1 1 d . . .
C16 C 0.9533(7) 0.0274(5) 0.6334(3) 0.0686(15) Uani 1 1 d . . .
H16 H 1.0325 -0.0260 0.6479 0.082 Uiso 1 1 calc R . .
C19 C 0.9217(7) 0.1110(5) 0.6767(2) 0.0603(14) Uani 1 1 d . . .
O3 O 0.6452(5) -0.0841(4) 0.0514(2) 0.0880(13) Uani 1 1 d . . .
C11 C 0.4988(7) 0.1026(5) 0.3715(2) 0.0635(15) Uani 1 1 d . . .
O6 O 1.2836(6) 0.3069(4) 0.0562(3) 0.1001(16) Uani 1 1 d . . .
O4 O 0.7320(7) -0.0149(6) 0.1457(2) 0.135(3) Uani 1 1 d . . .
C14 C 0.7513(8) 0.0968(6) 0.5461(3) 0.0721(18) Uani 1 1 d . . .
N5 N 1.0068(8) 0.1171(5) 0.7403(2) 0.0938(18) Uani 1 1 d . . .
H5A H 0.9852 0.1694 0.7666 0.113 Uiso 1 1 calc R . .
H5B H 1.0816 0.0687 0.7538 0.113 Uiso 1 1 calc R . .
C8 C 0.5244(8) 0.0146(5) 0.3312(3) 0.0727(17) Uani 1 1 d . . .
H8 H 0.6034 -0.0385 0.3465 0.087 Uiso 1 1 calc R . .
C18 C 0.8010(8) 0.1871(5) 0.6534(3) 0.0701(16) Uani 1 1 d . . .
H18 H 0.7762 0.2442 0.6813 0.084 Uiso 1 1 calc R . .
O5 O 1.3263(8) 0.1766(7) 0.1220(3) 0.193(4) Uani 1 1 d . . .
C15 C 0.8706(8) 0.0219(5) 0.5701(3) 0.0743(17) Uani 1 1 d . . .
H15 H 0.8963 -0.0350 0.5422 0.089 Uiso 1 1 calc R . .
C7 C 0.4359(8) 0.0044(5) 0.2696(3) 0.0758(17) Uani 1 1 d . . .
H7 H 0.4554 -0.0551 0.2427 0.091 Uiso 1 1 calc R . .
C17 C 0.7163(7) 0.1801(6) 0.5894(3) 0.0777(19) Uani 1 1 d . . .
H17 H 0.6343 0.2320 0.5750 0.093 Uiso 1 1 calc R . .
C10 C 0.3821(9) 0.1793(5) 0.3448(3) 0.0821(18) Uani 1 1 d . . .
H10 H 0.3625 0.2414 0.3694 0.098 Uiso 1 1 calc R . .
C12 C 0.5759(11) 0.1224(8) 0.4383(3) 0.128(4) Uani 1 1 d D . .
H12 H 0.5374 0.1883 0.4539 0.153 Uiso 1 1 calc R . .
C9 C 0.2964(8) 0.1647(6) 0.2834(4) 0.087(2) Uani 1 1 d . . .
H9 H 0.2176 0.2168 0.2662 0.104 Uiso 1 1 calc R . .
C13 C 0.6696(10) 0.0831(9) 0.4787(4) 0.138(4) Uani 1 1 d D . .
H13 H 0.7073 0.0179 0.4618 0.166 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
O7 C6 1.242(5) . ?
C3 C2 1.360(6) . ?
C3 N2 1.448(6) . ?
C3 C6 1.447(6) . ?
C6 C5 1.456(6) . ?
C5 C4 1.358(6) . ?
C5 N3 1.457(6) . ?
C4 C1 1.386(6) . ?
C4 H4 0.9300 . ?
O2 N1 1.222(5) . ?
N1 O1 1.233(6) . ?
N1 C1 1.443(6) . ?
C1 C2 1.378(6) . ?
C2 H2 0.9300 . ?
N3 O4 1.181(6) . ?
N3 O3 1.235(6) . ?
N4 C9 1.311(8) . ?
N4 C7 1.316(8) . ?
N4 H4A 0.8600 . ?
N2 O5 1.184(7) . ?
N2 O6 1.202(6) . ?
C16 C15 1.361(8) . ?
C16 C19 1.384(8) . ?
C16 H16 0.9300 . ?
C19 N5 1.374(6) . ?
C19 C18 1.378(8) . ?
C11 C10 1.382(9) . ?
C11 C8 1.376(8) . ?
C11 C12 1.427(8) . ?
C14 C15 1.365(9) . ?
C14 C17 1.389(9) . ?
C14 C13 1.439(9) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
C8 C7 1.354(8) . ?
C8 H8 0.9300 . ?
C18 C17 1.380(8) . ?
C18 H18 0.9300 . ?
C15 H15 0.9300 . ?
C7 H7 0.9300 . ?
C17 H17 0.9300 . ?
C10 C9 1.347(9) . ?
C10 H10 0.9300 . ?
C12 C13 1.139(9) . ?
C12 H12 0.9300 . ?
C9 H9 0.9300 . ?
C13 H13 0.9300 . ?

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 C3 N2 115.7(4) . . ?
C2 C3 C6 124.7(4) . . ?
N2 C3 C6 119.5(4) . . ?
O7 C6 C3 125.4(4) . . ?
O7 C6 C5 123.8(4) . . ?
C3 C6 C5 110.7(4) . . ?
C4 C5 C6 125.1(4) . . ?
C4 C5 N3 116.4(4) . . ?
C6 C5 N3 118.5(4) . . ?
C5 C4 C1 118.9(4) . . ?
C5 C4 H4 120.5 . . ?
C1 C4 H4 120.5 . . ?
O2 N1 O1 123.1(4) . . ?
O2 N1 C1 118.8(4) . . ?
O1 N1 C1 118.0(4) . . ?
C2 C1 C4 120.8(4) . . ?
C2 C1 N1 119.5(4) . . ?
C4 C1 N1 119.7(4) . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
O4 N3 O3 122.0(5) . . ?
O4 N3 C5 120.3(5) . . ?
O3 N3 C5 117.7(5) . . ?
C9 N4 C7 121.0(5) . . ?
C9 N4 H4A 119.5 . . ?
C7 N4 H4A 119.5 . . ?
O5 N2 O6 120.7(5) . . ?
O5 N2 C3 119.4(5) . . ?
O6 N2 C3 119.6(5) . . ?
C15 C16 C19 121.3(6) . . ?
C15 C16 H16 119.4 . . ?
C19 C16 H16 119.4 . . ?
N5 C19 C18 121.6(6) . . ?
N5 C19 C16 121.2(6) . . ?
C18 C19 C16 117.3(5) . . ?
C10 C11 C8 116.3(5) . . ?
C10 C11 C12 116.2(7) . . ?
C8 C11 C12 127.5(7) . . ?
C15 C14 C17 117.0(5) . . ?
C15 C14 C13 118.0(8) . . ?
C17 C14 C13 125.0(8) . . ?
C19 N5 H5A 120.0 . . ?
C19 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C7 C8 C11 120.8(6) . . ?
C7 C8 H8 119.6 . . ?
C11 C8 H8 119.6 . . ?
C17 C18 C19 121.0(6) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C16 C15 C14 122.3(6) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
N4 C7 C8 120.3(6) . . ?
N4 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C18 C17 C14 121.1(6) . . ?
C18 C17 H17 119.4 . . ?
C14 C17 H17 119.4 . . ?
C9 C10 C11 120.5(6) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C13 C12 C11 140.1(12) . . ?
C13 C12 H12 110.0 . . ?
C11 C12 H12 110.0 . . ?
N4 C9 C10 121.0(6) . . ?
N4 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C12 C13 C14 143.3(12) . . ?
C12 C13 H13 108.3 . . ?
C14 C13 H13 108.3 . . ?

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
C2 C3 C6 O7 177.3(5) . . . . ?
N2 C3 C6 O7 -2.4(7) . . . . ?
C2 C3 C6 C5 -1.4(7) . . . . ?
N2 C3 C6 C5 178.9(4) . . . . ?
O7 C6 C5 C4 -174.6(5) . . . . ?
C3 C6 C5 C4 4.2(7) . . . . ?
O7 C6 C5 N3 4.1(7) . . . . ?
C3 C6 C5 N3 -177.1(4) . . . . ?
C6 C5 C4 C1 -3.6(7) . . . . ?
N3 C5 C4 C1 177.7(4) . . . . ?
C5 C4 C1 C2 -0.2(7) . . . . ?
C5 C4 C1 N1 178.9(4) . . . . ?
O2 N1 C1 C2 178.9(4) . . . . ?
O1 N1 C1 C2 -0.7(7) . . . . ?
O2 N1 C1 C4 -0.2(7) . . . . ?
O1 N1 C1 C4 -179.8(4) . . . . ?
N2 C3 C2 C1 177.9(4) . . . . ?
C6 C3 C2 C1 -1.9(7) . . . . ?
C4 C1 C2 C3 2.8(7) . . . . ?
N1 C1 C2 C3 -176.3(4) . . . . ?
C4 C5 N3 O4 -152.0(6) . . . . ?
C6 C5 N3 O4 29.2(8) . . . . ?
C4 C5 N3 O3 29.1(7) . . . . ?
C6 C5 N3 O3 -149.7(5) . . . . ?
C2 C3 N2 O5 -153.9(7) . . . . ?
C6 C3 N2 O5 25.9(9) . . . . ?
C2 C3 N2 O6 20.7(8) . . . . ?
C6 C3 N2 O6 -159.5(5) . . . . ?
C15 C16 C19 N5 -179.2(5) . . . . ?
C15 C16 C19 C18 1.2(8) . . . . ?
C10 C11 C8 C7 -1.3(9) . . . . ?
C12 C11 C8 C7 177.0(6) . . . . ?
N5 C19 C18 C17 -180.0(5) . . . . ?
C16 C19 C18 C17 -0.3(8) . . . . ?
C19 C16 C15 C14 -0.9(9) . . . . ?
C17 C14 C15 C16 -0.3(9) . . . . ?
C13 C14 C15 C16 -179.3(6) . . . . ?
C9 N4 C7 C8 2.3(9) . . . . ?
C11 C8 C7 N4 -0.7(9) . . . . ?
C19 C18 C17 C14 -0.8(9) . . . . ?
C15 C14 C17 C18 1.1(8) . . . . ?
C13 C14 C17 C18 -180.0(5) . . . . ?
C8 C11 C10 C9 1.9(9) . . . . ?
C12 C11 C10 C9 -176.6(6) . . . . ?
C10 C11 C12 C13 177.6(10) . . . . ?
C8 C11 C12 C13 -0.7(14) . . . . ?
C7 N4 C9 C10 -1.7(10) . . . . ?
C11 C10 C9 N4 -0.5(10) . . . . ?
C11 C12 C13 C14 -179.2(7) . . . . ?
C15 C14 C13 C12 -175.5(10) . . . . ?
C17 C14 C13 C12 5.5(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 987872'
