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

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#                                CCDC 
# 
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# 
#  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
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data_130117d

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N4 O2'
_chemical_formula_weight         336.39

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'
O O 0.0106 0.0060 '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'

_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                   7.7983(8)
_cell_length_b                   15.7822(14)
_cell_length_c                   14.3700(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.5090(10)
_cell_angle_gamma                90.00
_cell_volume                     1749.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    997
_cell_measurement_theta_min      2.5759
_cell_measurement_theta_max      28.3012

_exptl_crystal_description       colorless
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   sadabs

_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  '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            6043
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.1022
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3081
_reflns_number_gt                1942
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0265P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3081
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N1 N 0.1272(3) 0.53053(12) 0.61014(16) 0.0193(5) Uani 1 1 d . . .
N2 N 0.1853(3) 0.55860(12) 0.46224(16) 0.0232(6) Uani 1 1 d . . .
H2A H 0.0922 0.5325 0.4386 0.028 Uiso 1 1 calc R . .
H2B H 0.2511 0.5809 0.4258 0.028 Uiso 1 1 calc R . .
N3 N 0.5959(3) 0.63329(13) 0.46852(18) 0.0287(6) Uani 1 1 d . . .
N4 N 0.4472(4) 0.43967(15) 0.8778(2) 0.0402(7) Uani 1 1 d . . .
O1 O 0.0644(2) 0.52315(11) 0.75897(14) 0.0293(5) Uani 1 1 d . . .
O2 O 0.2376(3) 0.80707(12) 0.83280(15) 0.0403(6) Uani 1 1 d . . .
C1 C 0.2271(4) 0.56445(15) 0.55404(19) 0.0175(6) Uani 1 1 d . . .
C2 C 0.1712(4) 0.53613(15) 0.7060(2) 0.0206(7) Uani 1 1 d . . .
C3 C 0.3601(4) 0.55690(15) 0.75015(19) 0.0195(7) Uani 1 1 d . . .
C4 C 0.3664(4) 0.64684(15) 0.7958(2) 0.0223(7) Uani 1 1 d . . .
H4 H 0.2879 0.6482 0.8430 0.027 Uiso 1 1 calc R . .
C5 C 0.3053(3) 0.71022(16) 0.71923(19) 0.0186(6) Uani 1 1 d . . .
C6 C 0.3218(3) 0.69925(15) 0.6289(2) 0.0166(6) Uani 1 1 d . . .
C7 C 0.3899(3) 0.61456(15) 0.59553(18) 0.0166(6) Uani 1 1 d . . .
C8 C 0.4831(4) 0.55773(15) 0.67591(19) 0.0194(6) Uani 1 1 d . . .
H8 H 0.4882 0.5000 0.6512 0.023 Uiso 1 1 calc R . .
C9 C 0.6678(4) 0.58429(16) 0.7166(2) 0.0242(7) Uani 1 1 d . . .
H9A H 0.7203 0.5396 0.7576 0.029 Uiso 1 1 calc R . .
H9B H 0.7352 0.5901 0.6654 0.029 Uiso 1 1 calc R . .
C10 C 0.6785(4) 0.66699(17) 0.7719(2) 0.0289(7) Uani 1 1 d . . .
H10A H 0.6524 0.7140 0.7286 0.035 Uiso 1 1 calc R . .
H10B H 0.7957 0.6745 0.8044 0.035 Uiso 1 1 calc R . .
C11 C 0.5516(4) 0.66754(17) 0.8435(2) 0.0277(7) Uani 1 1 d . . .
H11A H 0.5528 0.7229 0.8730 0.033 Uiso 1 1 calc R . .
H11B H 0.5880 0.6261 0.8923 0.033 Uiso 1 1 calc R . .
C12 C 0.2327(4) 0.79189(17) 0.7486(2) 0.0254(7) Uani 1 1 d . . .
C13 C 0.1624(4) 0.85418(16) 0.6751(2) 0.0277(8) Uani 1 1 d . . .
H13A H 0.2497 0.8972 0.6709 0.033 Uiso 1 1 calc R . .
H13B H 0.0629 0.8820 0.6949 0.033 Uiso 1 1 calc R . .
C14 C 0.1074(4) 0.81669(15) 0.5772(2) 0.0244(7) Uani 1 1 d . . .
C15 C 0.2603(4) 0.76324(15) 0.55341(19) 0.0212(7) Uani 1 1 d . . .
H15A H 0.2251 0.7338 0.4944 0.025 Uiso 1 1 calc R . .
H15B H 0.3557 0.8006 0.5451 0.025 Uiso 1 1 calc R . .
C16 C 0.5056(4) 0.62715(15) 0.5240(2) 0.0183(6) Uani 1 1 d . . .
C17 C 0.4109(4) 0.49152(18) 0.8229(2) 0.0259(7) Uani 1 1 d . . .
C18 C 0.0686(4) 0.88794(16) 0.5051(2) 0.0362(9) Uani 1 1 d . . .
H18A H -0.0237 0.9225 0.5214 0.054 Uiso 1 1 calc R . .
H18B H 0.0347 0.8640 0.4437 0.054 Uiso 1 1 calc R . .
H18C H 0.1705 0.9220 0.5049 0.054 Uiso 1 1 calc R . .
C19 C -0.0554(4) 0.76173(17) 0.5750(2) 0.0351(8) Uani 1 1 d . . .
H19A H -0.1491 0.7959 0.5905 0.053 Uiso 1 1 calc R . .
H19B H -0.0324 0.7166 0.6199 0.053 Uiso 1 1 calc R . .
H19C H -0.0867 0.7383 0.5132 0.053 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
N1 C1 1.315(3) . ?
N1 C2 1.373(3) . ?
N2 C1 1.314(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C16 1.143(3) . ?
N4 C17 1.143(3) . ?
O1 C2 1.225(3) . ?
O2 C12 1.229(3) . ?
C1 C7 1.539(4) . ?
C2 C3 1.550(4) . ?
C3 C17 1.480(4) . ?
C3 C8 1.537(4) . ?
C3 C4 1.561(3) . ?
C4 C5 1.511(4) . ?
C4 C11 1.540(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.334(4) . ?
C5 C12 1.493(3) . ?
C6 C15 1.508(3) . ?
C6 C7 1.541(3) . ?
C7 C16 1.478(3) . ?
C7 C8 1.555(3) . ?
C8 C9 1.531(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.524(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.530(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.487(4) . ?
C13 C14 1.528(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C18 1.529(4) . ?
C14 C19 1.534(4) . ?
C14 C15 1.540(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C1 N1 C2 120.4(2) . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C1 N1 120.3(3) . . ?
N2 C1 C7 119.5(2) . . ?
N1 C1 C7 120.1(2) . . ?
O1 C2 N1 121.3(3) . . ?
O1 C2 C3 118.3(3) . . ?
N1 C2 C3 120.4(2) . . ?
C17 C3 C8 111.5(2) . . ?
C17 C3 C2 106.3(2) . . ?
C8 C3 C2 111.8(2) . . ?
C17 C3 C4 110.4(2) . . ?
C8 C3 C4 107.4(2) . . ?
C2 C3 C4 109.4(2) . . ?
C5 C4 C11 111.0(2) . . ?
C5 C4 C3 108.0(2) . . ?
C11 C4 C3 110.4(2) . . ?
C5 C4 H4 109.1 . . ?
C11 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C6 C5 C12 118.8(2) . . ?
C6 C5 C4 123.8(2) . . ?
C12 C5 C4 117.3(2) . . ?
C5 C6 C15 123.2(2) . . ?
C5 C6 C7 120.2(2) . . ?
C15 C6 C7 116.4(2) . . ?
C16 C7 C1 110.7(2) . . ?
C16 C7 C6 112.0(2) . . ?
C1 C7 C6 105.3(2) . . ?
C16 C7 C8 109.1(2) . . ?
C1 C7 C8 105.05(19) . . ?
C6 C7 C8 114.4(2) . . ?
C9 C8 C3 112.7(2) . . ?
C9 C8 C7 115.8(2) . . ?
C3 C8 C7 104.4(2) . . ?
C9 C8 H8 107.8 . . ?
C3 C8 H8 107.8 . . ?
C7 C8 H8 107.8 . . ?
C10 C9 C8 114.2(2) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 111.4(2) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C4 110.9(2) . . ?
C10 C11 H11A 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O2 C12 C13 121.7(2) . . ?
O2 C12 C5 119.2(3) . . ?
C13 C12 C5 119.1(3) . . ?
C12 C13 C14 114.9(2) . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 C18 109.9(2) . . ?
C13 C14 C19 110.9(2) . . ?
C18 C14 C19 108.8(3) . . ?
C13 C14 C15 107.2(2) . . ?
C18 C14 C15 109.5(2) . . ?
C19 C14 C15 110.6(2) . . ?
C6 C15 C14 112.4(2) . . ?
C6 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C6 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
N3 C16 C7 177.1(3) . . ?
N4 C17 C3 178.3(3) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C2 N1 C1 N2 179.6(2) . . . . ?
C2 N1 C1 C7 -3.0(4) . . . . ?
C1 N1 C2 O1 162.9(2) . . . . ?
C1 N1 C2 C3 -18.7(4) . . . . ?
O1 C2 C3 C17 49.2(3) . . . . ?
N1 C2 C3 C17 -129.2(2) . . . . ?
O1 C2 C3 C8 171.1(2) . . . . ?
N1 C2 C3 C8 -7.3(3) . . . . ?
O1 C2 C3 C4 -70.0(3) . . . . ?
N1 C2 C3 C4 111.6(3) . . . . ?
C17 C3 C4 C5 -177.3(2) . . . . ?
C8 C3 C4 C5 60.9(3) . . . . ?
C2 C3 C4 C5 -60.7(3) . . . . ?
C17 C3 C4 C11 61.1(3) . . . . ?
C8 C3 C4 C11 -60.7(3) . . . . ?
C2 C3 C4 C11 177.8(2) . . . . ?
C11 C4 C5 C6 93.1(3) . . . . ?
C3 C4 C5 C6 -28.1(4) . . . . ?
C11 C4 C5 C12 -82.8(3) . . . . ?
C3 C4 C5 C12 156.0(2) . . . . ?
C12 C5 C6 C15 -4.0(4) . . . . ?
C4 C5 C6 C15 -179.9(2) . . . . ?
C12 C5 C6 C7 -177.8(2) . . . . ?
C4 C5 C6 C7 6.3(4) . . . . ?
N2 C1 C7 C16 -17.6(3) . . . . ?
N1 C1 C7 C16 165.0(2) . . . . ?
N2 C1 C7 C6 103.6(3) . . . . ?
N1 C1 C7 C6 -73.8(3) . . . . ?
N2 C1 C7 C8 -135.2(2) . . . . ?
N1 C1 C7 C8 47.4(3) . . . . ?
C5 C6 C7 C16 -141.5(3) . . . . ?
C15 C6 C7 C16 44.3(3) . . . . ?
C5 C6 C7 C1 98.1(3) . . . . ?
C15 C6 C7 C1 -76.1(3) . . . . ?
C5 C6 C7 C8 -16.7(4) . . . . ?
C15 C6 C7 C8 169.1(2) . . . . ?
C17 C3 C8 C9 -65.3(3) . . . . ?
C2 C3 C8 C9 175.9(2) . . . . ?
C4 C3 C8 C9 55.8(3) . . . . ?
C17 C3 C8 C7 168.2(2) . . . . ?
C2 C3 C8 C7 49.3(3) . . . . ?
C4 C3 C8 C7 -70.7(3) . . . . ?
C16 C7 C8 C9 49.6(3) . . . . ?
C1 C7 C8 C9 168.3(2) . . . . ?
C6 C7 C8 C9 -76.7(3) . . . . ?
C16 C7 C8 C3 174.2(2) . . . . ?
C1 C7 C8 C3 -67.1(2) . . . . ?
C6 C7 C8 C3 47.9(3) . . . . ?
C3 C8 C9 C10 -51.7(3) . . . . ?
C7 C8 C9 C10 68.4(3) . . . . ?
C8 C9 C10 C11 49.1(3) . . . . ?
C9 C10 C11 C4 -53.3(3) . . . . ?
C5 C4 C11 C10 -59.1(3) . . . . ?
C3 C4 C11 C10 60.7(3) . . . . ?
C6 C5 C12 O2 -170.7(3) . . . . ?
C4 C5 C12 O2 5.5(4) . . . . ?
C6 C5 C12 C13 7.1(4) . . . . ?
C4 C5 C12 C13 -176.8(2) . . . . ?
O2 C12 C13 C14 -159.9(3) . . . . ?
C5 C12 C13 C14 22.5(4) . . . . ?
C12 C13 C14 C18 -169.9(2) . . . . ?
C12 C13 C14 C19 69.8(3) . . . . ?
C12 C13 C14 C15 -51.0(3) . . . . ?
C5 C6 C15 C14 -27.7(4) . . . . ?
C7 C6 C15 C14 146.3(2) . . . . ?
C13 C14 C15 C6 53.0(3) . . . . ?
C18 C14 C15 C6 172.1(2) . . . . ?
C19 C14 C15 C6 -68.0(3) . . . . ?
C1 C7 C16 N3 -63(6) . . . . ?
C6 C7 C16 N3 180(100) . . . . ?
C8 C7 C16 N3 52(6) . . . . ?
C8 C3 C17 N4 -95(10) . . . . ?
C2 C3 C17 N4 27(10) . . . . ?
C4 C3 C17 N4 145(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 1000128'
#######################################################################
#
#                 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_130420b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N4 O3'
_chemical_formula_weight         326.35

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.9219(8)
_cell_length_b                   10.2365(13)
_cell_length_c                   11.9557(14)
_cell_angle_alpha                108.694(2)
_cell_angle_beta                 105.2940(10)
_cell_angle_gamma                100.3700(10)
_cell_volume                     847.90(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    740
_cell_measurement_theta_min      2.785
_cell_measurement_theta_max      21.45

_exptl_crystal_description       colorless
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4301
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0913
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2940
_reflns_number_gt                1479
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0531P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.082(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2940
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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
N1 N 0.7731(3) 0.4941(2) 0.9098(2) 0.0408(6) Uani 1 1 d . . .
N2 N 0.9944(3) 0.7113(3) 1.0124(2) 0.0545(8) Uani 1 1 d . . .
H2A H 1.0393 0.8020 1.0323 0.065 Uiso 1 1 calc R . .
H2B H 1.0584 0.6652 1.0457 0.065 Uiso 1 1 calc R . .
N3 N 0.7877(3) 0.9729(3) 0.9225(3) 0.0639(9) Uani 1 1 d . . .
N4 N 0.6920(4) 0.4444(3) 0.5546(3) 0.0717(10) Uani 1 1 d . . .
O1 O 0.5935(2) 0.2707(2) 0.79748(19) 0.0477(6) Uani 1 1 d . . .
O2 O 0.1260(3) 0.1448(2) 0.4148(2) 0.0537(6) Uani 1 1 d . . .
O3 O 0.1727(3) -0.0457(2) 0.4577(2) 0.0590(7) Uani 1 1 d . . .
C1 C 0.4680(4) 0.1631(3) 0.6834(3) 0.0404(8) Uani 1 1 d . . .
C2 C 0.3431(4) 0.1950(3) 0.6064(3) 0.0391(8) Uani 1 1 d . . .
C3 C 0.3282(3) 0.3467(3) 0.6456(3) 0.0406(8) Uani 1 1 d . . .
H3 H 0.2729 0.3631 0.5695 0.049 Uiso 1 1 calc R . .
C4 C 0.5208(3) 0.4550(3) 0.7170(3) 0.0359(7) Uani 1 1 d . . .
C5 C 0.6352(4) 0.4120(3) 0.8144(3) 0.0371(7) Uani 1 1 d . . .
C6 C 0.8243(4) 0.6418(3) 0.9292(3) 0.0409(8) Uani 1 1 d . . .
C7 C 0.7093(4) 0.7015(3) 0.8700(3) 0.0424(8) Uani 1 1 d . . .
C8 C 0.5172(4) 0.6115(3) 0.7830(3) 0.0415(8) Uani 1 1 d . . .
H8 H 0.4790 0.6503 0.7185 0.050 Uiso 1 1 calc R . .
C9 C 0.3822(4) 0.6179(3) 0.8548(3) 0.0524(9) Uani 1 1 d . . .
H9A H 0.4279 0.5928 0.9263 0.063 Uiso 1 1 calc R . .
H9B H 0.3746 0.7158 0.8865 0.063 Uiso 1 1 calc R . .
C10 C 0.1921(4) 0.5167(3) 0.7727(3) 0.0597(10) Uani 1 1 d . . .
H10A H 0.1113 0.5237 0.8214 0.072 Uiso 1 1 calc R . .
H10B H 0.1429 0.5435 0.7027 0.072 Uiso 1 1 calc R . .
C11 C 0.2032(4) 0.3641(3) 0.7239(3) 0.0522(9) Uani 1 1 d . . .
H11A H 0.0816 0.2994 0.6727 0.063 Uiso 1 1 calc R . .
H11B H 0.2488 0.3372 0.7944 0.063 Uiso 1 1 calc R . .
C12 C 0.5040(4) 0.0231(3) 0.6759(3) 0.0573(10) Uani 1 1 d . . .
H12A H 0.4281 -0.0507 0.5955 0.086 Uiso 1 1 calc R . .
H12B H 0.4768 -0.0016 0.7414 0.086 Uiso 1 1 calc R . .
H12C H 0.6302 0.0315 0.6858 0.086 Uiso 1 1 calc R . .
C13 C 0.2073(4) 0.0823(4) 0.4874(3) 0.0418(8) Uani 1 1 d . . .
C14 C -0.0200(4) 0.0518(3) 0.2983(3) 0.0542(9) Uani 1 1 d . . .
H14A H -0.1063 -0.0155 0.3127 0.065 Uiso 1 1 calc R . .
H14B H 0.0285 -0.0022 0.2380 0.065 Uiso 1 1 calc R . .
C15 C -0.1111(5) 0.1496(4) 0.2507(3) 0.0727(11) Uani 1 1 d . . .
H15A H -0.1620 0.1997 0.3101 0.109 Uiso 1 1 calc R . .
H15B H -0.2068 0.0935 0.1712 0.109 Uiso 1 1 calc R . .
H15C H -0.0227 0.2181 0.2404 0.109 Uiso 1 1 calc R . .
C16 C 0.6197(4) 0.4509(3) 0.6261(3) 0.0441(8) Uani 1 1 d . . .
C17 C 0.7553(4) 0.8522(4) 0.9009(3) 0.0456(8) Uani 1 1 d . . .


_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 C5 1.264(3) . ?
N1 C6 1.417(3) . ?
N2 C6 1.344(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C17 1.143(3) . ?
N4 C16 1.139(4) . ?
O1 C5 1.359(3) . ?
O1 C1 1.410(3) . ?
O2 C13 1.336(3) . ?
O2 C14 1.445(3) . ?
O3 C13 1.200(3) . ?
C1 C2 1.327(4) . ?
C1 C12 1.490(4) . ?
C2 C13 1.486(4) . ?
C2 C3 1.508(4) . ?
C3 C11 1.528(4) . ?
C3 C4 1.544(4) . ?
C3 H3 0.9800 . ?
C4 C16 1.494(4) . ?
C4 C5 1.513(4) . ?
C4 C8 1.551(4) . ?
C6 C7 1.358(4) . ?
C7 C17 1.417(4) . ?
C7 C8 1.514(4) . ?
C8 C9 1.535(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.521(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.510(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.502(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C5 N1 C6 117.2(2) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C5 O1 C1 121.4(2) . . ?
C13 O2 C14 117.3(2) . . ?
C2 C1 O1 120.9(3) . . ?
C2 C1 C12 131.3(3) . . ?
O1 C1 C12 107.7(2) . . ?
C1 C2 C13 121.6(3) . . ?
C1 C2 C3 119.3(3) . . ?
C13 C2 C3 118.9(2) . . ?
C2 C3 C11 109.6(2) . . ?
C2 C3 C4 109.7(2) . . ?
C11 C3 C4 112.4(2) . . ?
C2 C3 H3 108.3 . . ?
C11 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C16 C4 C5 105.0(2) . . ?
C16 C4 C3 108.6(2) . . ?
C5 C4 C3 111.7(2) . . ?
C16 C4 C8 109.6(2) . . ?
C5 C4 C8 108.5(2) . . ?
C3 C4 C8 113.2(2) . . ?
N1 C5 O1 115.3(2) . . ?
N1 C5 C4 126.4(3) . . ?
O1 C5 C4 118.2(2) . . ?
N2 C6 C7 125.9(3) . . ?
N2 C6 N1 112.0(2) . . ?
C7 C6 N1 122.1(3) . . ?
C6 C7 C17 121.2(3) . . ?
C6 C7 C8 120.3(3) . . ?
C17 C7 C8 118.0(2) . . ?
C7 C8 C9 111.2(2) . . ?
C7 C8 C4 108.5(2) . . ?
C9 C8 C4 112.0(2) . . ?
C7 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C4 C8 H8 108.3 . . ?
C10 C9 C8 112.4(3) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 109.3(3) . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 C3 112.0(3) . . ?
C10 C11 H11A 109.2 . . ?
C3 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C3 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O2 123.7(3) . . ?
O3 C13 C2 126.8(3) . . ?
O2 C13 C2 109.5(3) . . ?
O2 C14 C15 105.9(3) . . ?
O2 C14 H14A 110.6 . . ?
C15 C14 H14A 110.6 . . ?
O2 C14 H14B 110.6 . . ?
C15 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C4 178.3(4) . . ?
N3 C17 C7 177.8(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
C5 O1 C1 C2 -22.8(4) . . . . ?
C5 O1 C1 C12 159.0(2) . . . . ?
O1 C1 C2 C13 -178.5(3) . . . . ?
C12 C1 C2 C13 -0.8(5) . . . . ?
O1 C1 C2 C3 -3.8(4) . . . . ?
C12 C1 C2 C3 174.0(3) . . . . ?
C1 C2 C3 C11 -86.3(3) . . . . ?
C13 C2 C3 C11 88.6(3) . . . . ?
C1 C2 C3 C4 37.6(4) . . . . ?
C13 C2 C3 C4 -147.5(3) . . . . ?
C2 C3 C4 C16 69.2(3) . . . . ?
C11 C3 C4 C16 -168.6(2) . . . . ?
C2 C3 C4 C5 -46.1(3) . . . . ?
C11 C3 C4 C5 76.1(3) . . . . ?
C2 C3 C4 C8 -168.9(2) . . . . ?
C11 C3 C4 C8 -46.7(3) . . . . ?
C6 N1 C5 O1 178.4(2) . . . . ?
C6 N1 C5 C4 1.2(4) . . . . ?
C1 O1 C5 N1 -167.1(2) . . . . ?
C1 O1 C5 C4 10.3(4) . . . . ?
C16 C4 C5 N1 84.3(3) . . . . ?
C3 C4 C5 N1 -158.2(3) . . . . ?
C8 C4 C5 N1 -32.8(4) . . . . ?
C16 C4 C5 O1 -92.9(3) . . . . ?
C3 C4 C5 O1 24.6(3) . . . . ?
C8 C4 C5 O1 150.0(2) . . . . ?
C5 N1 C6 N2 -164.4(3) . . . . ?
C5 N1 C6 C7 16.4(4) . . . . ?
N2 C6 C7 C17 -6.0(5) . . . . ?
N1 C6 C7 C17 173.0(3) . . . . ?
N2 C6 C7 C8 -177.0(3) . . . . ?
N1 C6 C7 C8 2.0(4) . . . . ?
C6 C7 C8 C9 90.3(3) . . . . ?
C17 C7 C8 C9 -81.0(3) . . . . ?
C6 C7 C8 C4 -33.3(4) . . . . ?
C17 C7 C8 C4 155.4(3) . . . . ?
C16 C4 C8 C7 -69.7(3) . . . . ?
C5 C4 C8 C7 44.4(3) . . . . ?
C3 C4 C8 C7 169.0(2) . . . . ?
C16 C4 C8 C9 167.1(2) . . . . ?
C5 C4 C8 C9 -78.7(3) . . . . ?
C3 C4 C8 C9 45.8(3) . . . . ?
C7 C8 C9 C10 -174.2(3) . . . . ?
C4 C8 C9 C10 -52.6(3) . . . . ?
C8 C9 C10 C11 59.3(4) . . . . ?
C9 C10 C11 C3 -59.8(4) . . . . ?
C2 C3 C11 C10 176.5(3) . . . . ?
C4 C3 C11 C10 54.2(3) . . . . ?
C14 O2 C13 O3 4.3(4) . . . . ?
C14 O2 C13 C2 -175.8(2) . . . . ?
C1 C2 C13 O3 13.7(5) . . . . ?
C3 C2 C13 O3 -161.1(3) . . . . ?
C1 C2 C13 O2 -166.1(3) . . . . ?
C3 C2 C13 O2 19.1(4) . . . . ?
C13 O2 C14 C15 168.3(3) . . . . ?
C5 C4 C16 N4 102(11) . . . . ?
C3 C4 C16 N4 -17(11) . . . . ?
C8 C4 C16 N4 -142(11) . . . . ?
C6 C7 C17 N3 169(10) . . . . ?
C8 C7 C17 N3 -20(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 1029241'
