# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1400834'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37

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)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.197(3)
_cell_length_b                   14.855(9)
_cell_length_c                   22.937(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.436(11)
_cell_angle_gamma                90.00
_cell_volume                     1762.9(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2330
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      26.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            5510
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3019
_reflns_number_gt                2352
_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)+(0.0732P)²+0.9583P] 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     SHELXL
_refine_ls_extinction_coef       0.040(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3019
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
C1 C 1.5341(5) 0.35934(18) 0.38443(11) 0.0590(7) Uani 1 1 d . . .
H1 H 1.5997 0.4147 0.3977 0.071 Uiso 1 1 calc R . .
C2 C 1.6489(6) 0.2804(2) 0.40485(13) 0.0666(8) Uani 1 1 d . . .
H2 H 1.7940 0.2828 0.4318 0.080 Uiso 1 1 calc R . .
C3 C 1.5517(6) 0.19724(19) 0.38587(12) 0.0653(7) Uani 1 1 d . . .
H3 H 1.6345 0.1451 0.4001 0.078 Uiso 1 1 calc R . .
C4 C 1.3354(5) 0.18998(17) 0.34643(11) 0.0549(7) Uani 1 1 d . . .
H4 H 1.2693 0.1343 0.3341 0.066 Uiso 1 1 calc R . .
C5 C 1.2212(4) 0.26976(15) 0.32610(9) 0.0428(5) Uani 1 1 d . . .
C6 C 1.3181(4) 0.35490(15) 0.34362(10) 0.0457(6) Uani 1 1 d . . .
C7 C 1.1622(5) 0.42272(15) 0.31220(10) 0.0451(6) Uani 1 1 d . . .
C8 C 0.9738(4) 0.37913(14) 0.27748(9) 0.0401(5) Uani 1 1 d . . .
C9 C 1.2141(6) 0.52227(16) 0.31321(11) 0.0572(7) Uani 1 1 d . . .
H9A H 1.3635 0.5341 0.2921 0.069 Uiso 1 1 calc R . .
H9B H 1.0673 0.5528 0.2927 0.069 Uiso 1 1 calc R . .
C10 C 1.0369(9) 0.5592(3) 0.40026(17) 0.1045(13) Uani 1 1 d . . .
H10A H 0.9763 0.4980 0.4045 0.125 Uiso 1 1 calc R . .
H10B H 0.9012 0.5930 0.3781 0.125 Uiso 1 1 calc R . .
C11 C 1.0924(13) 0.5997(3) 0.45804(19) 0.162(3) Uani 1 1 d . . .
H11A H 1.2242 0.5655 0.4803 0.244 Uiso 1 1 calc R . .
H11B H 0.9383 0.6000 0.4780 0.244 Uiso 1 1 calc R . .
H11C H 1.1513 0.6604 0.4538 0.244 Uiso 1 1 calc R . .
C12 C 0.8471(4) 0.22110(14) 0.25794(9) 0.0433(5) Uani 1 1 d . . .
C13 C 0.6134(4) 0.34526(14) 0.20822(9) 0.0416(5) Uani 1 1 d . . .
C14 C 0.7671(4) 0.40669(14) 0.23628(9) 0.0430(5) Uani 1 1 d . . .
H14 H 0.7388 0.4676 0.2288 0.052 Uiso 1 1 calc R . .
C15 C 0.3977(4) 0.36004(14) 0.16341(9) 0.0422(5) Uani 1 1 d . . .
C16 C 0.2269(5) 0.29175(15) 0.14432(10) 0.0469(6) Uani 1 1 d . . .
H16 H 0.2479 0.2348 0.1610 0.056 Uiso 1 1 calc R . .
C17 C 0.0264(5) 0.30644(17) 0.10113(11) 0.0520(6) Uani 1 1 d . . .
H17 H -0.0864 0.2599 0.0893 0.062 Uiso 1 1 calc R . .
C18 C -0.0053(5) 0.39026(18) 0.07568(10) 0.0529(6) Uani 1 1 d . . .
C19 C 0.1649(5) 0.45907(18) 0.09387(12) 0.0621(7) Uani 1 1 d . . .
H19 H 0.1447 0.5157 0.0767 0.075 Uiso 1 1 calc R . .
C20 C 0.3625(5) 0.44432(16) 0.13691(11) 0.0561(7) Uani 1 1 d . . .
H20 H 0.4744 0.4911 0.1486 0.067 Uiso 1 1 calc R . .
C21 C -0.3685(6) 0.3453(2) 0.01010(13) 0.0801(9) Uani 1 1 d . . .
H21A H -0.2750 0.2976 -0.0066 0.120 Uiso 1 1 calc R . .
H21B H -0.4903 0.3708 -0.0194 0.120 Uiso 1 1 calc R . .
H21C H -0.4591 0.3219 0.0414 0.120 Uiso 1 1 calc R . .
N1 N 1.0061(4) 0.28496(11) 0.28537(8) 0.0423(5) Uani 1 1 d . . .
O1 O 1.2591(4) 0.55871(12) 0.36993(8) 0.0673(6) Uani 1 1 d . . .
O2 O 0.8689(3) 0.14133(10) 0.26488(8) 0.0583(5) Uani 1 1 d . . .
O3 O 0.6516(3) 0.25338(9) 0.21991(7) 0.0481(4) Uani 1 1 d . . .
O4 O -0.1920(4) 0.41325(14) 0.03240(8) 0.0741(6) 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
C1 C2 1.378(4) . ?
C1 C6 1.393(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.405(3) . ?
C5 C6 1.406(3) . ?
C6 C7 1.442(3) . ?
C7 C8 1.365(3) . ?
C7 C9 1.503(3) . ?
C8 N1 1.419(3) . ?
C8 C14 1.422(3) . ?
C9 O1 1.408(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O1 1.404(4) . ?
C10 C11 1.459(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O2 1.200(3) . ?
C12 O3 1.362(3) . ?
C12 N1 1.371(3) . ?
C13 C14 1.337(3) . ?
C13 O3 1.401(3) . ?
C13 C15 1.464(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 C20 1.396(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C18 O4 1.364(3) . ?
C18 C19 1.390(4) . ?
C19 C20 1.373(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O4 1.426(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C2 C1 C6 118.9(2) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C1 C2 C3 121.2(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 116.8(2) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
C4 C5 N1 130.5(2) . . ?
C4 C5 C6 122.8(2) . . ?
N1 C5 C6 106.65(19) . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 C7 132.9(2) . . ?
C5 C6 C7 108.4(2) . . ?
C8 C7 C6 107.3(2) . . ?
C8 C7 C9 126.4(2) . . ?
C6 C7 C9 126.0(2) . . ?
C7 C8 N1 108.88(19) . . ?
C7 C8 C14 134.9(2) . . ?
N1 C8 C14 116.19(19) . . ?
O1 C9 C7 114.0(2) . . ?
O1 C9 H9A 108.8 . . ?
C7 C9 H9A 108.8 . . ?
O1 C9 H9B 108.8 . . ?
C7 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C11 110.6(4) . . ?
O1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 119.2(2) . . ?
O2 C12 N1 125.2(2) . . ?
O3 C12 N1 115.53(18) . . ?
C14 C13 O3 120.3(2) . . ?
C14 C13 C15 128.2(2) . . ?
O3 C13 C15 111.44(18) . . ?
C13 C14 C8 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C8 C14 H14 119.9 . . ?
C16 C15 C20 117.6(2) . . ?
C16 C15 C13 122.3(2) . . ?
C20 C15 C13 120.0(2) . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O4 C18 C17 125.6(2) . . ?
O4 C18 C19 115.0(2) . . ?
C17 C18 C19 119.3(2) . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C15 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 N1 C5 126.92(18) . . ?
C12 N1 C8 124.39(19) . . ?
C5 N1 C8 108.68(17) . . ?
C10 O1 C9 112.8(2) . . ?
C12 O3 C13 123.29(17) . . ?
C18 O4 C21 118.2(2) . . ?

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
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 N1 178.3(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C2 C1 C6 C5 1.8(4) . . . . ?
C2 C1 C6 C7 -176.9(3) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
N1 C5 C6 C1 179.9(2) . . . . ?
C4 C5 C6 C7 177.2(2) . . . . ?
N1 C5 C6 C7 -1.1(2) . . . . ?
C1 C6 C7 C8 179.8(3) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
C1 C6 C7 C9 5.2(4) . . . . ?
C5 C6 C7 C9 -173.6(2) . . . . ?
C6 C7 C8 N1 -0.6(2) . . . . ?
C9 C7 C8 N1 174.0(2) . . . . ?
C6 C7 C8 C14 -178.8(2) . . . . ?
C9 C7 C8 C14 -4.2(4) . . . . ?
C8 C7 C9 O1 135.8(2) . . . . ?
C6 C7 C9 O1 -50.6(3) . . . . ?
O3 C13 C14 C8 1.1(3) . . . . ?
C15 C13 C14 C8 -177.9(2) . . . . ?
C7 C8 C14 C13 179.3(2) . . . . ?
N1 C8 C14 C13 1.1(3) . . . . ?
C14 C13 C15 C16 -169.5(2) . . . . ?
O3 C13 C15 C16 11.4(3) . . . . ?
C14 C13 C15 C20 12.5(4) . . . . ?
O3 C13 C15 C20 -166.6(2) . . . . ?
C20 C15 C16 C17 -0.8(3) . . . . ?
C13 C15 C16 C17 -178.9(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C17 C18 O4 179.1(2) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
O4 C18 C19 C20 -179.6(2) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C16 C15 C20 C19 0.5(4) . . . . ?
C13 C15 C20 C19 178.5(2) . . . . ?
O2 C12 N1 C5 0.0(4) . . . . ?
O3 C12 N1 C5 -179.71(19) . . . . ?
O2 C12 N1 C8 -178.6(2) . . . . ?
O3 C12 N1 C8 1.7(3) . . . . ?
C4 C5 N1 C12 3.9(4) . . . . ?
C6 C5 N1 C12 -178.1(2) . . . . ?
C4 C5 N1 C8 -177.3(2) . . . . ?
C6 C5 N1 C8 0.7(2) . . . . ?
C7 C8 N1 C12 178.7(2) . . . . ?
C14 C8 N1 C12 -2.7(3) . . . . ?
C7 C8 N1 C5 -0.1(2) . . . . ?
C14 C8 N1 C5 178.51(18) . . . . ?
C11 C10 O1 C9 -178.5(3) . . . . ?
C7 C9 O1 C10 -69.2(3) . . . . ?
O2 C12 O3 C13 -178.9(2) . . . . ?
N1 C12 O3 C13 0.8(3) . . . . ?
C14 C13 O3 C12 -2.3(3) . . . . ?
C15 C13 O3 C12 176.98(18) . . . . ?
C17 C18 O4 C21 -1.3(4) . . . . ?
C19 C18 O4 C21 177.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.245

