# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1425307'
_audit_update_record             
;
2015-09-17 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N3 O2'
_chemical_formula_weight         379.41

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   P21/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                   15.462(3)
_cell_length_b                   9.2890(19)
_cell_length_c                   13.431(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.57(3)
_cell_angle_gamma                90.00
_cell_volume                     1828.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10
_cell_measurement_theta_max      13

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   ?

_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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3393
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         25.40
_reflns_number_total             3365
_reflns_number_gt                1948
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0660P)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         3365
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.44368(16) 0.0451(2) 0.09355(18) 0.0469(6) Uani 1 1 d . . .
C1 C 0.3576(2) 0.0807(3) 0.0534(2) 0.0480(7) Uani 1 1 d . . .
H1B H 0.3110 0.0135 0.0295 0.058 Uiso 1 1 calc R . .
O2 O 0.23351(15) 0.4110(3) 0.0495(2) 0.0821(8) Uani 1 1 d . . .
N2 N 0.48682(14) 0.1756(2) 0.11480(17) 0.0399(6) Uani 1 1 d . . .
O1 O 0.62837(13) 0.0722(2) 0.16139(16) 0.0542(6) Uani 1 1 d . . .
C2 C 0.58281(18) 0.1813(3) 0.1470(2) 0.0399(7) Uani 1 1 d . . .
N3 N 0.61717(14) 0.3181(2) 0.15831(17) 0.0400(6) Uani 1 1 d . . .
C3 C 0.56403(18) 0.4443(3) 0.1468(2) 0.0379(7) Uani 1 1 d . . .
C4 C 0.60326(19) 0.5807(3) 0.1671(2) 0.0459(7) Uani 1 1 d . . .
H4A H 0.6665 0.5889 0.1910 0.055 Uiso 1 1 calc R . .
C5 C 0.5510(2) 0.7033(3) 0.1524(2) 0.0485(7) Uani 1 1 d . . .
H5A H 0.5788 0.7932 0.1655 0.058 Uiso 1 1 calc R . .
C6 C 0.4570(2) 0.6926(3) 0.1183(2) 0.0485(8) Uani 1 1 d . . .
H6A H 0.4213 0.7752 0.1081 0.058 Uiso 1 1 calc R . .
C7 C 0.41655(19) 0.5594(3) 0.0993(2) 0.0437(7) Uani 1 1 d . . .
H7A H 0.3532 0.5532 0.0766 0.052 Uiso 1 1 calc R . .
C8 C 0.46779(18) 0.4331(3) 0.1130(2) 0.0371(6) Uani 1 1 d . . .
C9 C 0.42862(18) 0.2914(3) 0.0926(2) 0.0374(6) Uani 1 1 d . . .
C10 C 0.34190(18) 0.2317(3) 0.0499(2) 0.0422(7) Uani 1 1 d . . .
C11 C 0.25233(19) 0.3027(3) 0.0083(2) 0.0497(8) Uani 1 1 d . . .
C12 C 0.18277(18) 0.2432(3) -0.0863(2) 0.0457(7) Uani 1 1 d . . .
C13 C 0.2050(2) 0.1556(3) -0.1584(2) 0.0539(8) Uani 1 1 d . . .
H13A H 0.2652 0.1273 -0.1462 0.065 Uiso 1 1 calc R . .
C14 C 0.1378(2) 0.1101(4) -0.2484(3) 0.0704(10) Uani 1 1 d . . .
H14A H 0.1530 0.0524 -0.2969 0.084 Uiso 1 1 calc R . .
C15 C 0.0489(3) 0.1502(4) -0.2659(3) 0.0842(12) Uani 1 1 d . . .
H15A H 0.0038 0.1184 -0.3258 0.101 Uiso 1 1 calc R . .
C16 C 0.0260(2) 0.2373(4) -0.1952(3) 0.0785(11) Uani 1 1 d . . .
H16A H -0.0344 0.2643 -0.2075 0.094 Uiso 1 1 calc R . .
C17 C 0.0925(2) 0.2839(4) -0.1068(3) 0.0628(9) Uani 1 1 d . . .
H17A H 0.0768 0.3439 -0.0598 0.075 Uiso 1 1 calc R . .
C18 C 0.71638(17) 0.3307(3) 0.1742(2) 0.0487(8) Uani 1 1 d . . .
H18A H 0.7261 0.4112 0.1330 0.058 Uiso 1 1 calc R . .
H18B H 0.7365 0.2442 0.1476 0.058 Uiso 1 1 calc R . .
C19 C 0.77457(18) 0.3520(3) 0.2866(2) 0.0450(7) Uani 1 1 d . . .
C20 C 0.82692(19) 0.4754(3) 0.3177(3) 0.0562(8) Uani 1 1 d . . .
H20A H 0.8263 0.5461 0.2685 0.067 Uiso 1 1 calc R . .
C21 C 0.8799(2) 0.4938(4) 0.4213(3) 0.0640(9) Uani 1 1 d . . .
H21A H 0.9142 0.5772 0.4418 0.077 Uiso 1 1 calc R . .
C22 C 0.8819(2) 0.3891(4) 0.4936(3) 0.0691(10) Uani 1 1 d . . .
H22A H 0.9171 0.4021 0.5634 0.083 Uiso 1 1 calc R . .
C23 C 0.8322(2) 0.2648(4) 0.4635(3) 0.0648(10) Uani 1 1 d . . .
H23A H 0.8350 0.1932 0.5128 0.078 Uiso 1 1 calc R . .
C24 C 0.77857(19) 0.2459(3) 0.3611(2) 0.0521(8) Uani 1 1 d . . .
H24A H 0.7448 0.1618 0.3413 0.063 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 1.309(3) . ?
N1 N2 1.369(3) . ?
C1 C10 1.421(4) . ?
C1 H1B 0.9300 . ?
O2 C11 1.227(3) . ?
N2 C9 1.373(3) . ?
N2 C2 1.409(3) . ?
O1 C2 1.214(3) . ?
C2 N3 1.367(3) . ?
N3 C3 1.412(3) . ?
N3 C18 1.484(3) . ?
C3 C4 1.393(4) . ?
C3 C8 1.415(4) . ?
C4 C5 1.375(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.374(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.394(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.439(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.474(4) . ?
C11 C12 1.485(4) . ?
C12 C17 1.387(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.386(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.370(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.376(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.370(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.504(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.388(4) . ?
C19 C24 1.392(4) . ?
C20 C21 1.382(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.368(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.374(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.373(4) . ?
C23 H23A 0.9300 . ?
C24 H24A 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
C1 N1 N2 103.0(2) . . ?
N1 C1 C10 113.8(3) . . ?
N1 C1 H1B 123.1 . . ?
C10 C1 H1B 123.1 . . ?
N1 N2 C9 114.0(2) . . ?
N1 N2 C2 119.5(2) . . ?
C9 N2 C2 126.2(2) . . ?
O1 C2 N3 125.0(2) . . ?
O1 C2 N2 121.2(2) . . ?
N3 C2 N2 113.8(2) . . ?
C2 N3 C3 124.6(2) . . ?
C2 N3 C18 115.9(2) . . ?
C3 N3 C18 119.3(2) . . ?
C4 C3 N3 122.1(2) . . ?
C4 C3 C8 118.5(2) . . ?
N3 C3 C8 119.4(2) . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4A 119.1 . . ?
C3 C4 H4A 119.1 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C6 C7 C8 121.8(3) . . ?
C6 C7 H7A 119.1 . . ?
C8 C7 H7A 119.1 . . ?
C7 C8 C3 118.4(2) . . ?
C7 C8 C9 123.9(2) . . ?
C3 C8 C9 117.7(2) . . ?
N2 C9 C10 104.8(2) . . ?
N2 C9 C8 117.9(2) . . ?
C10 C9 C8 137.2(3) . . ?
C9 C10 C1 104.3(2) . . ?
C9 C10 C11 130.0(3) . . ?
C1 C10 C11 125.7(3) . . ?
O2 C11 C10 121.6(3) . . ?
O2 C11 C12 118.7(3) . . ?
C10 C11 C12 119.7(3) . . ?
C17 C12 C13 118.6(3) . . ?
C17 C12 C11 118.5(3) . . ?
C13 C12 C11 122.8(3) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16A 120.1 . . ?
C15 C16 H16A 120.1 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17A 119.5 . . ?
C12 C17 H17A 119.5 . . ?
N3 C18 C19 114.5(2) . . ?
N3 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
N3 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C24 118.7(3) . . ?
C20 C19 C18 121.1(3) . . ?
C24 C19 C18 120.2(3) . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21A 120.0 . . ?
C20 C21 H21A 120.0 . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C23 C24 C19 120.2(3) . . ?
C23 C24 H24A 119.9 . . ?
C19 C24 H24A 119.9 . . ?

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
N2 N1 C1 C10 -1.6(3) . . . . ?
C1 N1 N2 C9 2.6(3) . . . . ?
C1 N1 N2 C2 -171.9(2) . . . . ?
N1 N2 C2 O1 -3.8(4) . . . . ?
C9 N2 C2 O1 -177.5(2) . . . . ?
N1 N2 C2 N3 175.5(2) . . . . ?
C9 N2 C2 N3 1.8(4) . . . . ?
O1 C2 N3 C3 -176.4(3) . . . . ?
N2 C2 N3 C3 4.3(4) . . . . ?
O1 C2 N3 C18 9.3(4) . . . . ?
N2 C2 N3 C18 -170.0(2) . . . . ?
C2 N3 C3 C4 175.1(3) . . . . ?
C18 N3 C3 C4 -10.8(4) . . . . ?
C2 N3 C3 C8 -5.4(4) . . . . ?
C18 N3 C3 C8 168.7(2) . . . . ?
N3 C3 C4 C5 177.9(2) . . . . ?
C8 C3 C4 C5 -1.6(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C3 -0.4(4) . . . . ?
C6 C7 C8 C9 -179.0(3) . . . . ?
C4 C3 C8 C7 1.3(4) . . . . ?
N3 C3 C8 C7 -178.2(2) . . . . ?
C4 C3 C8 C9 -180.0(2) . . . . ?
N3 C3 C8 C9 0.5(4) . . . . ?
N1 N2 C9 C10 -2.5(3) . . . . ?
C2 N2 C9 C10 171.5(2) . . . . ?
N1 N2 C9 C8 179.6(2) . . . . ?
C2 N2 C9 C8 -6.3(4) . . . . ?
C7 C8 C9 N2 -176.5(2) . . . . ?
C3 C8 C9 N2 4.9(3) . . . . ?
C7 C8 C9 C10 6.5(5) . . . . ?
C3 C8 C9 C10 -172.0(3) . . . . ?
N2 C9 C10 C1 1.4(3) . . . . ?
C8 C9 C10 C1 178.6(3) . . . . ?
N2 C9 C10 C11 -178.0(3) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
N1 C1 C10 C9 0.1(3) . . . . ?
N1 C1 C10 C11 179.5(3) . . . . ?
C9 C10 C11 O2 -38.1(5) . . . . ?
C1 C10 C11 O2 142.7(3) . . . . ?
C9 C10 C11 C12 141.5(3) . . . . ?
C1 C10 C11 C12 -37.7(4) . . . . ?
O2 C11 C12 C17 -18.4(4) . . . . ?
C10 C11 C12 C17 162.0(3) . . . . ?
O2 C11 C12 C13 157.6(3) . . . . ?
C10 C11 C12 C13 -22.0(4) . . . . ?
C17 C12 C13 C14 -0.2(4) . . . . ?
C11 C12 C13 C14 -176.2(3) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C16 0.9(6) . . . . ?
C14 C15 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 C12 -0.9(6) . . . . ?
C13 C12 C17 C16 1.0(5) . . . . ?
C11 C12 C17 C16 177.2(3) . . . . ?
C2 N3 C18 C19 -99.8(3) . . . . ?
C3 N3 C18 C19 85.5(3) . . . . ?
N3 C18 C19 C20 -118.4(3) . . . . ?
N3 C18 C19 C24 63.2(3) . . . . ?
C24 C19 C20 C21 -1.8(4) . . . . ?
C18 C19 C20 C21 179.8(3) . . . . ?
C19 C20 C21 C22 0.9(5) . . . . ?
C20 C21 C22 C23 0.7(5) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C22 C23 C24 C19 0.5(5) . . . . ?
C20 C19 C24 C23 1.1(4) . . . . ?
C18 C19 C24 C23 179.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.045
