# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p1bar
_database_code_depnum_ccdc_archive 'CCDC 1484156'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N3 O3'
_chemical_formula_weight         345.35

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'
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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   6.9694(14)
_cell_length_b                   8.0346(16)
_cell_length_c                   15.190(3)
_cell_angle_alpha                84.71(3)
_cell_angle_beta                 77.42(3)
_cell_angle_gamma                87.21(3)
_cell_volume                     826.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    18299
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      29.2

_exptl_crystal_description       irregular
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.096
_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      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  'Stoe IPDS-II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6123
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2900
_reflns_number_gt                1914
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (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 > 2σ(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)+(0.0458P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2900
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   0.837
_refine_ls_restrained_S_all      0.837
_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
O1 O 0.79145(16) 0.62427(14) 0.44470(7) 0.0654(3) Uani 1 1 d . . .
N1 N -0.07387(17) 0.98126(14) 0.22360(7) 0.0446(3) Uani 1 1 d . . .
C19 C 0.1627(2) 0.75141(19) 0.07995(9) 0.0507(4) Uani 1 1 d . . .
H19 H 0.1566 0.8600 0.0533 0.061 Uiso 1 1 calc R . .
C13 C 0.0748(2) 0.86266(17) 0.23271(9) 0.0438(3) Uani 1 1 d . . .
C17 C 0.2198(2) 0.46037(18) 0.06590(9) 0.0463(4) Uani 1 1 d . . .
C7 C 0.3134(2) 0.82890(17) 0.34254(9) 0.0446(3) Uani 1 1 d . . .
C12 C 0.4665(2) 0.73775(18) 0.29123(9) 0.0476(4) Uani 1 1 d . . .
H12 H 0.4639 0.7221 0.2316 0.057 Uiso 1 1 calc R . .
C10 C 0.6315(2) 0.69384(18) 0.41536(9) 0.0492(4) Uani 1 1 d . . .
N2 N 0.05182(18) 1.04636(15) 0.34029(8) 0.0516(3) Uani 1 1 d . . .
C5 C -0.0828(2) 1.08902(18) 0.29148(9) 0.0471(4) Uani 1 1 d . . .
C18 C 0.2095(2) 0.6198(2) 0.02568(9) 0.0514(4) Uani 1 1 d . . .
H18 H 0.2337 0.6390 -0.0370 0.062 Uiso 1 1 calc R . .
C11 C 0.6209(2) 0.67069(19) 0.32712(10) 0.0496(4) Uani 1 1 d . . .
H11 H 0.7198 0.6089 0.2917 0.059 Uiso 1 1 calc R . .
N3 N 0.26967(19) 0.32131(19) 0.00743(10) 0.0608(4) Uani 1 1 d . . .
C1 C -0.2068(2) 0.99541(19) 0.16835(10) 0.0528(4) Uani 1 1 d . . .
H1 H -0.2012 0.9201 0.1248 0.063 Uiso 1 1 calc R . .
C14 C 0.1245(2) 0.72349(17) 0.17402(9) 0.0427(3) Uani 1 1 d . . .
C15 C 0.1358(2) 0.55968(18) 0.21236(9) 0.0465(4) Uani 1 1 d . . .
H15 H 0.1103 0.5391 0.2750 0.056 Uiso 1 1 calc R . .
O3 O 0.3117(2) 0.35481(17) -0.07457(9) 0.0846(4) Uani 1 1 d . . .
O2 O 0.2641(2) 0.17861(17) 0.04340(10) 0.0941(5) Uani 1 1 d . . .
C16 C 0.1843(2) 0.42720(18) 0.15872(10) 0.0493(4) Uani 1 1 d . . .
H16 H 0.1927 0.3183 0.1846 0.059 Uiso 1 1 calc R . .
C6 C 0.1492(2) 0.90691(18) 0.30472(9) 0.0448(3) Uani 1 1 d . . .
C4 C -0.2260(2) 1.2208(2) 0.29885(10) 0.0569(4) Uani 1 1 d . . .
H4 H -0.2322 1.2970 0.3419 0.068 Uiso 1 1 calc R . .
C9 C 0.4814(2) 0.7856(2) 0.46699(10) 0.0572(4) Uani 1 1 d . . .
H9 H 0.4861 0.8036 0.5261 0.069 Uiso 1 1 calc R . .
C2 C -0.3457(2) 1.1196(2) 0.17769(10) 0.0590(4) Uani 1 1 d . . .
H2 H -0.4368 1.1289 0.1408 0.071 Uiso 1 1 calc R . .
C8 C 0.3251(2) 0.8502(2) 0.43095(9) 0.0547(4) Uani 1 1 d . . .
H8 H 0.2248 0.9097 0.4669 0.066 Uiso 1 1 calc R . .
C3 C -0.3540(2) 1.2355(2) 0.24311(11) 0.0629(4) Uani 1 1 d . . .
H3 H -0.4479 1.3224 0.2478 0.075 Uiso 1 1 calc R . .
C20 C 0.8075(3) 0.6513(3) 0.53450(13) 0.0905(7) Uani 1 1 d . . .
H20A H 0.8036 0.7693 0.5410 0.136 Uiso 1 1 calc R . .
H20B H 0.9295 0.6028 0.5456 0.136 Uiso 1 1 calc R . .
H20C H 0.7000 0.6001 0.5773 0.136 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C10 1.3654(17) . ?
O1 C20 1.4297(19) . ?
N1 C1 1.3735(18) . ?
N1 C13 1.3938(18) . ?
N1 C5 1.3958(17) . ?
C19 C18 1.383(2) . ?
C19 C14 1.3943(19) . ?
C19 H19 0.9300 . ?
C13 C6 1.3886(18) . ?
C13 C14 1.4754(19) . ?
C17 C18 1.373(2) . ?
C17 C16 1.380(2) . ?
C17 N3 1.4726(19) . ?
C7 C8 1.3896(18) . ?
C7 C12 1.396(2) . ?
C7 C6 1.477(2) . ?
C12 C11 1.375(2) . ?
C12 H12 0.9300 . ?
C10 C9 1.388(2) . ?
C10 C11 1.3882(19) . ?
N2 C5 1.3312(19) . ?
N2 C6 1.3732(18) . ?
C5 C4 1.414(2) . ?
C18 H18 0.9300 . ?
C11 H11 0.9300 . ?
N3 O2 1.2224(18) . ?
N3 O3 1.2234(18) . ?
C1 C2 1.351(2) . ?
C1 H1 0.9300 . ?
C14 C15 1.395(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C4 C3 1.351(2) . ?
C4 H4 0.9300 . ?
C9 C8 1.381(2) . ?
C9 H9 0.9300 . ?
C2 C3 1.414(2) . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C10 O1 C20 117.47(13) . . ?
C1 N1 C13 131.88(12) . . ?
C1 N1 C5 121.50(12) . . ?
C13 N1 C5 106.39(11) . . ?
C18 C19 C14 120.89(14) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C6 C13 N1 105.42(11) . . ?
C6 C13 C14 132.17(13) . . ?
N1 C13 C14 122.40(12) . . ?
C18 C17 C16 122.10(13) . . ?
C18 C17 N3 118.42(14) . . ?
C16 C17 N3 119.48(14) . . ?
C8 C7 C12 117.09(13) . . ?
C8 C7 C6 120.48(12) . . ?
C12 C7 C6 122.37(12) . . ?
C11 C12 C7 121.30(13) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
O1 C10 C9 124.79(13) . . ?
O1 C10 C11 116.81(13) . . ?
C9 C10 C11 118.40(13) . . ?
C5 N2 C6 105.78(11) . . ?
N2 C5 N1 111.38(12) . . ?
N2 C5 C4 130.43(13) . . ?
N1 C5 C4 118.19(13) . . ?
C17 C18 C19 118.92(14) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C12 C11 C10 121.01(14) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
O2 N3 O3 123.56(14) . . ?
O2 N3 C17 118.23(15) . . ?
O3 N3 C17 118.20(15) . . ?
C2 C1 N1 119.50(14) . . ?
C2 C1 H1 120.3 . . ?
N1 C1 H1 120.3 . . ?
C19 C14 C15 118.50(13) . . ?
C19 C14 C13 121.47(13) . . ?
C15 C14 C13 120.03(12) . . ?
C16 C15 C14 121.12(14) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 118.47(14) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
N2 C6 C13 111.03(12) . . ?
N2 C6 C7 119.77(12) . . ?
C13 C6 C7 129.17(12) . . ?
C3 C4 C5 119.81(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C8 C9 C10 120.24(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C1 C2 C3 120.56(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C9 C8 C7 121.94(14) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C4 C3 C2 120.34(15) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C1 N1 C13 C6 -175.13(14) . . . . ?
C5 N1 C13 C6 -0.84(15) . . . . ?
C1 N1 C13 C14 3.9(2) . . . . ?
C5 N1 C13 C14 178.20(13) . . . . ?
C8 C7 C12 C11 0.6(2) . . . . ?
C6 C7 C12 C11 177.95(14) . . . . ?
C20 O1 C10 C9 -1.5(2) . . . . ?
C20 O1 C10 C11 178.14(15) . . . . ?
C6 N2 C5 N1 -0.80(17) . . . . ?
C6 N2 C5 C4 178.92(16) . . . . ?
C1 N1 C5 N2 176.07(13) . . . . ?
C13 N1 C5 N2 1.05(16) . . . . ?
C1 N1 C5 C4 -3.7(2) . . . . ?
C13 N1 C5 C4 -178.70(14) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
N3 C17 C18 C19 179.98(13) . . . . ?
C14 C19 C18 C17 -0.6(2) . . . . ?
C7 C12 C11 C10 -1.1(2) . . . . ?
O1 C10 C11 C12 -179.23(14) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C18 C17 N3 O2 -174.55(14) . . . . ?
C16 C17 N3 O2 5.2(2) . . . . ?
C18 C17 N3 O3 4.4(2) . . . . ?
C16 C17 N3 O3 -175.78(14) . . . . ?
C13 N1 C1 C2 175.75(15) . . . . ?
C5 N1 C1 C2 2.2(2) . . . . ?
C18 C19 C14 C15 0.4(2) . . . . ?
C18 C19 C14 C13 179.88(14) . . . . ?
C6 C13 C14 C19 -129.51(17) . . . . ?
N1 C13 C14 C19 51.7(2) . . . . ?
C6 C13 C14 C15 50.0(2) . . . . ?
N1 C13 C14 C15 -128.79(15) . . . . ?
C19 C14 C15 C16 0.2(2) . . . . ?
C13 C14 C15 C16 -179.29(13) . . . . ?
C18 C17 C16 C15 0.4(2) . . . . ?
N3 C17 C16 C15 -179.39(13) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C5 N2 C6 C13 0.24(17) . . . . ?
C5 N2 C6 C7 178.54(13) . . . . ?
N1 C13 C6 N2 0.40(16) . . . . ?
C14 C13 C6 N2 -178.51(15) . . . . ?
N1 C13 C6 C7 -177.70(14) . . . . ?
C14 C13 C6 C7 3.4(3) . . . . ?
C8 C7 C6 N2 24.4(2) . . . . ?
C12 C7 C6 N2 -152.78(14) . . . . ?
C8 C7 C6 C13 -157.61(15) . . . . ?
C12 C7 C6 C13 25.2(2) . . . . ?
N2 C5 C4 C3 -177.27(17) . . . . ?
N1 C5 C4 C3 2.4(2) . . . . ?
O1 C10 C9 C8 -179.72(15) . . . . ?
C11 C10 C9 C8 0.6(2) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
C10 C9 C8 C7 -1.1(3) . . . . ?
C12 C7 C8 C9 0.5(2) . . . . ?
C6 C7 C8 C9 -176.91(15) . . . . ?
C5 C4 C3 C2 0.2(3) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031
