# 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_nk_ard_n_met_0m
_database_code_depnum_ccdc_archive 'CCDC 1025207'
_audit_update_record             
;
2015-05-02 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 N2 O4'
_chemical_formula_weight         410.41

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.9732(6)
_cell_length_b                   11.0621(8)
_cell_length_c                   11.7442(8)
_cell_angle_alpha                78.303(2)
_cell_angle_beta                 80.056(2)
_cell_angle_gamma                75.760(2)
_cell_volume                     974.90(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11951
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         26.47
_reflns_number_total             3872
_reflns_number_gt                3151
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0761P)²+0.1625P] 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         3872
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.86720(18) -0.15089(12) 1.04093(11) 0.0708(4) Uani 1 1 d . . .
O2 O 0.7153(2) -0.26346(13) 0.99095(14) 0.0961(5) Uani 1 1 d . . .
O3 O 0.64812(13) 0.50560(9) 0.60979(9) 0.0473(3) Uani 1 1 d . . .
O4 O 1.04883(16) 0.10954(10) 0.64933(10) 0.0639(3) Uani 1 1 d . . .
N1 N 1.04529(17) 0.23736(12) 0.47082(11) 0.0494(3) Uani 1 1 d . . .
N2 N 0.7611(2) -0.16388(12) 0.98287(12) 0.0570(4) Uani 1 1 d . . .
C1 C 0.9871(2) 0.49600(19) 0.21736(14) 0.0629(5) Uani 1 1 d . . .
H1 H 1.0321 0.5134 0.1388 0.075 Uiso 1 1 calc R . .
C2 C 1.0522(2) 0.38127(18) 0.28273(14) 0.0573(4) Uani 1 1 d . . .
H2 H 1.1413 0.3227 0.2487 0.069 Uiso 1 1 calc R . .
C3 C 0.98369(19) 0.35265(14) 0.40131(13) 0.0444(3) Uani 1 1 d . . .
C9 C 0.98334(19) 0.20872(13) 0.58873(13) 0.0455(3) Uani 1 1 d . . .
C8 C 0.83903(17) 0.30084(12) 0.63698(12) 0.0384(3) Uani 1 1 d . . .
C13 C 0.76924(18) 0.27020(12) 0.76463(12) 0.0388(3) Uani 1 1 d . . .
H9 H 0.8655 0.2557 0.8110 0.047 Uiso 1 1 calc R . .
C14 C 0.69369(17) 0.15191(12) 0.79232(11) 0.0384(3) Uani 1 1 d . . .
C15 C 0.75976(17) 0.04988(12) 0.87407(12) 0.0402(3) Uani 1 1 d . . .
H10 H 0.8515 0.0519 0.9124 0.048 Uiso 1 1 calc R . .
C16 C 0.68690(18) -0.05493(13) 0.89760(12) 0.0430(3) Uani 1 1 d . . .
C17 C 0.5492(2) -0.06244(14) 0.84529(14) 0.0503(4) Uani 1 1 d . . .
H11 H 0.5030 -0.1345 0.8631 0.060 Uiso 1 1 calc R . .
C18 C 0.4817(2) 0.04070(15) 0.76535(15) 0.0544(4) Uani 1 1 d . . .
H12 H 0.3871 0.0395 0.7294 0.065 Uiso 1 1 calc R . .
C19 C 0.55503(19) 0.14561(14) 0.73902(13) 0.0481(4) Uani 1 1 d . . .
H13 H 0.5100 0.2138 0.6840 0.058 Uiso 1 1 calc R . .
C12 C 0.63235(18) 0.38170(13) 0.79944(12) 0.0421(3) Uani 1 1 d . . .
H8 H 0.5821 0.3758 0.8774 0.051 Uiso 1 1 calc R . .
C11 C 0.57829(18) 0.48753(12) 0.72715(12) 0.0398(3) Uani 1 1 d . . .
C7 C 0.77920(17) 0.41208(13) 0.56980(12) 0.0386(3) Uani 1 1 d . . .
C10 C 1.1829(3) 0.14059(19) 0.42042(18) 0.0745(6) Uani 1 1 d . . .
H5 H 1.2107 0.0679 0.4799 0.112 Uiso 1 1 calc R . .
H6 H 1.2851 0.1742 0.3908 0.112 Uiso 1 1 calc R . .
H7 H 1.1428 0.1164 0.3576 0.112 Uiso 1 1 calc R . .
C6 C 0.8567(2) 0.58630(18) 0.26530(15) 0.0617(5) Uani 1 1 d . . .
H4 H 0.8156 0.6638 0.2198 0.074 Uiso 1 1 calc R . .
C5 C 0.7889(2) 0.56026(15) 0.38056(14) 0.0499(4) Uani 1 1 d . . .
H3 H 0.7014 0.6207 0.4134 0.060 Uiso 1 1 calc R . .
C4 C 0.84980(18) 0.44355(13) 0.44964(12) 0.0410(3) Uani 1 1 d . . .
C20 C 0.44429(18) 0.60043(13) 0.75481(14) 0.0434(3) Uani 1 1 d . . .
C21 C 0.4024(2) 0.70490(14) 0.66822(15) 0.0527(4) Uani 1 1 d . . .
H14 H 0.4589 0.7042 0.5921 0.063 Uiso 1 1 calc R . .
C22 C 0.2761(2) 0.81077(15) 0.69489(18) 0.0612(5) Uani 1 1 d . . .
H15 H 0.2484 0.8800 0.6363 0.073 Uiso 1 1 calc R . .
C23 C 0.1926(2) 0.81349(16) 0.80668(19) 0.0643(5) Uani 1 1 d . . .
H16 H 0.1098 0.8849 0.8243 0.077 Uiso 1 1 calc R . .
C24 C 0.2314(2) 0.71057(18) 0.89267(18) 0.0646(5) Uani 1 1 d . . .
H17 H 0.1739 0.7122 0.9685 0.078 Uiso 1 1 calc R . .
C25 C 0.3555(2) 0.60433(16) 0.86753(15) 0.0556(4) Uani 1 1 d . . .
H18 H 0.3799 0.5349 0.9265 0.067 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
O1 N2 1.2244(19) . ?
O2 N2 1.2246(19) . ?
O3 C7 1.3707(17) . ?
O3 C11 1.3883(17) . ?
O4 C9 1.2299(17) . ?
N1 C9 1.3874(19) . ?
N1 C3 1.3936(19) . ?
N1 C10 1.468(2) . ?
N2 C16 1.4731(19) . ?
C1 C2 1.374(3) . ?
C1 C6 1.382(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.408(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(2) . ?
C9 C8 1.4545(19) . ?
C8 C7 1.3461(18) . ?
C8 C13 1.5069(18) . ?
C13 C12 1.5060(18) . ?
C13 C14 1.5259(19) . ?
C13 H9 0.9800 . ?
C14 C19 1.383(2) . ?
C14 C15 1.3841(18) . ?
C15 C16 1.380(2) . ?
C15 H10 0.9300 . ?
C16 C17 1.374(2) . ?
C17 C18 1.382(2) . ?
C17 H11 0.9300 . ?
C18 C19 1.382(2) . ?
C18 H12 0.9300 . ?
C19 H13 0.9300 . ?
C12 C11 1.3237(19) . ?
C12 H8 0.9300 . ?
C11 C20 1.4815(19) . ?
C7 C4 1.433(2) . ?
C10 H5 0.9600 . ?
C10 H6 0.9600 . ?
C10 H7 0.9600 . ?
C6 C5 1.369(2) . ?
C6 H4 0.9300 . ?
C5 C4 1.401(2) . ?
C5 H3 0.9300 . ?
C20 C21 1.390(2) . ?
C20 C25 1.393(2) . ?
C21 C22 1.394(2) . ?
C21 H14 0.9300 . ?
C22 C23 1.368(3) . ?
C22 H15 0.9300 . ?
C23 C24 1.371(3) . ?
C23 H16 0.9300 . ?
C24 C25 1.384(2) . ?
C24 H17 0.9300 . ?
C25 H18 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
C7 O3 C11 118.51(10) . . ?
C9 N1 C3 122.75(12) . . ?
C9 N1 C10 117.09(13) . . ?
C3 N1 C10 120.16(13) . . ?
O1 N2 O2 123.29(15) . . ?
O1 N2 C16 118.44(13) . . ?
O2 N2 C16 118.26(16) . . ?
C2 C1 C6 121.76(15) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C1 C2 C3 119.84(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
N1 C3 C4 119.74(12) . . ?
N1 C3 C2 121.81(14) . . ?
C4 C3 C2 118.45(14) . . ?
O4 C9 N1 120.97(13) . . ?
O4 C9 C8 121.83(13) . . ?
N1 C9 C8 117.19(12) . . ?
C7 C8 C9 119.92(12) . . ?
C7 C8 C13 122.26(12) . . ?
C9 C8 C13 117.71(11) . . ?
C12 C13 C8 109.28(11) . . ?
C12 C13 C14 110.00(11) . . ?
C8 C13 C14 112.73(11) . . ?
C12 C13 H9 108.2 . . ?
C8 C13 H9 108.2 . . ?
C14 C13 H9 108.2 . . ?
C19 C14 C15 118.63(13) . . ?
C19 C14 C13 120.91(12) . . ?
C15 C14 C13 120.44(12) . . ?
C16 C15 C14 118.76(13) . . ?
C16 C15 H10 120.6 . . ?
C14 C15 H10 120.6 . . ?
C17 C16 C15 123.20(13) . . ?
C17 C16 N2 118.67(13) . . ?
C15 C16 N2 118.13(14) . . ?
C16 C17 C18 117.78(14) . . ?
C16 C17 H11 121.1 . . ?
C18 C17 H11 121.1 . . ?
C19 C18 C17 119.85(15) . . ?
C19 C18 H12 120.1 . . ?
C17 C18 H12 120.1 . . ?
C18 C19 C14 121.77(13) . . ?
C18 C19 H13 119.1 . . ?
C14 C19 H13 119.1 . . ?
C11 C12 C13 124.76(12) . . ?
C11 C12 H8 117.6 . . ?
C13 C12 H8 117.6 . . ?
C12 C11 O3 121.59(12) . . ?
C12 C11 C20 127.77(13) . . ?
O3 C11 C20 110.63(11) . . ?
C8 C7 O3 123.51(12) . . ?
C8 C7 C4 122.44(13) . . ?
O3 C7 C4 114.04(11) . . ?
N1 C10 H5 109.5 . . ?
N1 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
N1 C10 H7 109.5 . . ?
H5 C10 H7 109.5 . . ?
H6 C10 H7 109.5 . . ?
C5 C6 C1 119.20(16) . . ?
C5 C6 H4 120.4 . . ?
C1 C6 H4 120.4 . . ?
C6 C5 C4 120.75(16) . . ?
C6 C5 H3 119.6 . . ?
C4 C5 H3 119.6 . . ?
C5 C4 C3 119.98(13) . . ?
C5 C4 C7 122.24(13) . . ?
C3 C4 C7 117.78(13) . . ?
C21 C20 C25 118.22(14) . . ?
C21 C20 C11 120.69(14) . . ?
C25 C20 C11 121.09(13) . . ?
C20 C21 C22 120.37(16) . . ?
C20 C21 H14 119.8 . . ?
C22 C21 H14 119.8 . . ?
C23 C22 C21 120.46(16) . . ?
C23 C22 H15 119.8 . . ?
C21 C22 H15 119.8 . . ?
C22 C23 C24 119.76(15) . . ?
C22 C23 H16 120.1 . . ?
C24 C23 H16 120.1 . . ?
C23 C24 C25 120.53(17) . . ?
C23 C24 H17 119.7 . . ?
C25 C24 H17 119.7 . . ?
C24 C25 C20 120.65(16) . . ?
C24 C25 H18 119.7 . . ?
C20 C25 H18 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.036
