# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_PS148

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2013-06-13
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C15 H12 N4 O4'
_chemical_formula_weight         312.09

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.187(5)
_cell_length_b                   8.453(5)
_cell_length_c                   12.382(5)
_cell_angle_alpha                93.382(5)
_cell_angle_beta                 95.364(5)
_cell_angle_gamma                107.885(5)
_cell_volume                     709.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_number            12449
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_full        28.19
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_reflns_number_total             3426
_reflns_number_gt                2801
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0930P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3426
_refine_ls_number_parameters     214
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   0.92
_refine_ls_restrained_S_all      0.919
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.6770(2) 0.08682(16) 0.17433(11) 0.0364(3) Uani 1 1 d . . .
C2 C 0.55242(19) 0.18957(16) 0.13067(11) 0.0365(3) Uani 1 1 d . . .
H2A H 0.4895 0.1429 0.0581 0.044 Uiso 1 1 calc R . .
H2B H 0.4503 0.1868 0.1772 0.044 Uiso 1 1 calc R . .
C3 C 0.72034(19) 0.44853(17) 0.03555(10) 0.0343(3) Uani 1 1 d . . .
C4 C 0.6721(2) 0.3983(2) -0.07537(11) 0.0439(3) Uani 1 1 d . . .
H4 H 0.5974 0.2897 -0.1015 0.053 Uiso 1 1 calc R . .
C5 C 0.7425(3) 0.5204(2) -0.14400(13) 0.0526(4) Uani 1 1 d . . .
H5 H 0.7132 0.4933 -0.2189 0.063 Uiso 1 1 calc R . .
C6 C 0.8562(2) 0.6831(2) -0.10496(14) 0.0521(4) Uani 1 1 d . . .
H6 H 0.9014 0.7603 -0.1546 0.062 Uiso 1 1 calc R . .
C7 C 0.9034(2) 0.73275(19) 0.00482(13) 0.0450(3) Uani 1 1 d . . .
H7 H 0.9792 0.8412 0.0306 0.054 Uiso 1 1 calc R . .
C8 C 0.83110(19) 0.61120(17) 0.07494(11) 0.0363(3) Uani 1 1 d . . .
C9 C 0.75786(18) 0.46642(15) 0.21705(10) 0.0319(3) Uani 1 1 d . . .
C10 C 0.74588(18) 0.41755(16) 0.32751(10) 0.0330(3) Uani 1 1 d . . .
C11 C 0.74843(19) 0.25814(17) 0.35336(10) 0.0337(3) Uani 1 1 d . . .
C12 C 0.7471(2) 0.2224(2) 0.46197(12) 0.0460(4) Uani 1 1 d . . .
H12 H 0.749 0.1177 0.4802 0.055 Uiso 1 1 calc R . .
C13 C 0.7430(3) 0.3407(2) 0.54234(12) 0.0527(4) Uani 1 1 d . . .
H13 H 0.7419 0.3147 0.6143 0.063 Uiso 1 1 calc R . .
C14 C 0.7404(3) 0.4972(2) 0.51776(13) 0.0495(4) Uani 1 1 d . . .
H14 H 0.7378 0.5761 0.5727 0.059 Uiso 1 1 calc R . .
C15 C 0.7418(2) 0.53569(18) 0.41107(11) 0.0406(3) Uani 1 1 d . . .
H15 H 0.7399 0.6411 0.3943 0.049 Uiso 1 1 calc R . .
N1 N 0.76788(17) 0.13477(14) 0.27732(10) 0.0373(3) Uani 1 1 d D . .
H1 H 0.832(2) 0.070(2) 0.3046(14) 0.045 Uiso 1 1 d D . .
N2 N 0.67609(16) 0.36182(13) 0.12708(8) 0.0320(2) Uani 1 1 d . . .
N3 N 0.84979(17) 0.61772(14) 0.18790(9) 0.0362(3) Uani 1 1 d D . .
H3 H 0.915(2) 0.7099(19) 0.2331(13) 0.043 Uiso 1 1 d D . .
N4 N 1.16822(19) 0.98808(15) 0.30171(10) 0.0439(3) Uani 1 1 d . . .
O1 O 0.69595(19) -0.03093(14) 0.11964(9) 0.0537(3) Uani 1 1 d . . .
O2 O 1.2528(2) 0.91305(18) 0.24530(15) 0.0816(5) Uani 1 1 d . . .
O3 O 0.99916(16) 0.90805(14) 0.32529(10) 0.0511(3) Uani 1 1 d . . .
O4 O 1.2422(2) 1.13626(16) 0.33220(13) 0.0736(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.2203(17) . ?
C1 N1 1.3557(18) . ?
C1 C2 1.5134(19) . ?
C2 N2 1.4602(18) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.392(2) . ?
C3 C8 1.392(2) . ?
C3 N2 1.3947(17) . ?
C4 C5 1.381(2) . ?
C4 H4 0.93 . ?
C5 C6 1.396(3) . ?
C5 H5 0.93 . ?
C6 C7 1.378(2) . ?
C6 H6 0.93 . ?
C7 C8 1.393(2) . ?
C7 H7 0.93 . ?
C8 N3 1.3887(18) . ?
C9 N3 1.3351(18) . ?
C9 N2 1.3455(17) . ?
C9 C10 1.4546(19) . ?
C10 C15 1.4037(19) . ?
C10 C11 1.408(2) . ?
C11 C12 1.396(2) . ?
C11 N1 1.4114(17) . ?
C12 C13 1.377(2) . ?
C12 H12 0.93 . ?
C13 C14 1.380(3) . ?
C13 H13 0.93 . ?
C14 C15 1.379(2) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
N1 H1 0.881(14) . ?
N3 H3 0.902(14) . ?
N4 O4 1.2214(18) . ?
N4 O2 1.234(2) . ?
N4 O3 1.2665(18) . ?

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
O1 C1 N1 122.09(13) . . ?
O1 C1 C2 121.95(13) . . ?
N1 C1 C2 115.95(12) . . ?
N2 C2 C1 109.73(12) . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C8 122.38(13) . . ?
C4 C3 N2 131.61(14) . . ?
C8 C3 N2 106.01(11) . . ?
C5 C4 C3 115.54(16) . . ?
C5 C4 H4 122.2 . . ?
C3 C4 H4 122.2 . . ?
C4 C5 C6 122.32(15) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C7 C6 C5 122.08(14) . . ?
C7 C6 H6 119 . . ?
C5 C6 H6 119 . . ?
C6 C7 C8 116.14(15) . . ?
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
N3 C8 C3 107.12(11) . . ?
N3 C8 C7 131.34(14) . . ?
C3 C8 C7 121.53(14) . . ?
N3 C9 N2 109.26(12) . . ?
N3 C9 C10 126.70(12) . . ?
N2 C9 C10 124.04(12) . . ?
C15 C10 C11 119.40(12) . . ?
C15 C10 C9 118.83(12) . . ?
C11 C10 C9 121.70(11) . . ?
C12 C11 C10 118.76(12) . . ?
C12 C11 N1 117.02(12) . . ?
C10 C11 N1 124.03(12) . . ?
C13 C12 C11 120.64(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.00(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.50(14) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 120.70(14) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C1 N1 C11 128.78(12) . . ?
C1 N1 H1 115.9(12) . . ?
C11 N1 H1 114.5(12) . . ?
C9 N2 C3 108.84(11) . . ?
C9 N2 C2 123.09(11) . . ?
C3 N2 C2 127.96(11) . . ?
C9 N3 C8 108.74(11) . . ?
C9 N3 H3 126.6(11) . . ?
C8 N3 H3 124.7(11) . . ?
O4 N4 O2 121.45(15) . . ?
O4 N4 O3 120.43(14) . . ?
O2 N4 O3 118.11(14) . . ?

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
O1 C1 C2 N2 -117.47(15) . . . . ?
N1 C1 C2 N2 61.78(16) . . . . ?
C8 C3 C4 C5 0.4(2) . . . . ?
N2 C3 C4 C5 179.94(13) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C4 C3 C8 N3 179.52(12) . . . . ?
N2 C3 C8 N3 -0.12(13) . . . . ?
C4 C3 C8 C7 -1.2(2) . . . . ?
N2 C3 C8 C7 179.12(11) . . . . ?
C6 C7 C8 N3 -179.96(13) . . . . ?
C6 C7 C8 C3 1.0(2) . . . . ?
N3 C9 C10 C15 32.39(19) . . . . ?
N2 C9 C10 C15 -148.01(13) . . . . ?
N3 C9 C10 C11 -144.33(14) . . . . ?
N2 C9 C10 C11 35.27(18) . . . . ?
C15 C10 C11 C12 -0.10(19) . . . . ?
C9 C10 C11 C12 176.61(13) . . . . ?
C15 C10 C11 N1 -174.90(12) . . . . ?
C9 C10 C11 N1 1.81(19) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
N1 C11 C12 C13 175.28(14) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C10 -0.1(2) . . . . ?
C11 C10 C15 C14 0.1(2) . . . . ?
C9 C10 C15 C14 -176.73(13) . . . . ?
O1 C1 N1 C11 -174.36(14) . . . . ?
C2 C1 N1 C11 6.4(2) . . . . ?
C12 C11 N1 C1 140.84(15) . . . . ?
C10 C11 N1 C1 -44.3(2) . . . . ?
N3 C9 N2 C3 1.19(14) . . . . ?
C10 C9 N2 C3 -178.47(11) . . . . ?
N3 C9 N2 C2 -175.38(11) . . . . ?
C10 C9 N2 C2 4.95(18) . . . . ?
C4 C3 N2 C9 179.77(14) . . . . ?
C8 C3 N2 C9 -0.64(13) . . . . ?
C4 C3 N2 C2 -3.9(2) . . . . ?
C8 C3 N2 C2 175.72(12) . . . . ?
C1 C2 N2 C9 -69.77(15) . . . . ?
C1 C2 N2 C3 114.34(13) . . . . ?
N2 C9 N3 C8 -1.26(14) . . . . ?
C10 C9 N3 C8 178.39(12) . . . . ?
C3 C8 N3 C9 0.84(14) . . . . ?
C7 C8 N3 C9 -178.29(14) . . . . ?


# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 972698'
