# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_000000
_database_code_depnum_ccdc_archive 'CCDC 1440441'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2015-12-08 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 H19 N O4'
_chemical_formula_weight         385.40

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pcca '

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

_cell_length_a                   15.751(8)
_cell_length_b                   14.741(7)
_cell_length_c                   8.621(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2001.7(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2355
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      22.50

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_T_max  0.9844
_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  '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            13244
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1774
_reflns_number_gt                1336
_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)+(0.0539P)²+0.7284P] 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       0.0056(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1774
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 0.5000 0.88172(14) 0.2500 0.0397(6) Uani 1 2 d S . .
O1 O 0.04071(9) 0.59321(11) 0.0879(2) 0.0604(5) Uani 1 1 d . . .
O2 O 0.10419(10) 0.50079(12) -0.0823(2) 0.0686(6) Uani 1 1 d . . .
H2 H 0.0568 0.4779 -0.0840 0.103 Uiso 1 1 calc R . .
C12 C 0.27571(12) 0.73206(13) 0.1613(2) 0.0404(5) Uani 1 1 d . . .
C3 C 0.44607(12) 1.02623(13) 0.1522(2) 0.0389(5) Uani 1 1 d . . .
H3 H 0.4098 0.9952 0.0856 0.047 Uiso 1 1 calc R . .
C4 C 0.5000 0.97807(16) 0.2500 0.0336(6) Uani 1 2 d S . .
C13 C 0.19764(13) 0.68092(13) 0.1328(3) 0.0439(5) Uani 1 1 d . . .
H13 H 0.1506 0.6971 0.1919 0.053 Uiso 1 1 calc R . .
C7 C 0.42403(11) 0.83279(12) 0.2198(2) 0.0362(5) Uani 1 1 d . . .
C15 C 0.10479(14) 0.56781(13) 0.0143(3) 0.0464(5) Uani 1 1 d . . .
C2 C 0.44633(13) 1.11992(13) 0.1537(3) 0.0439(5) Uani 1 1 d . . .
H2A H 0.4097 1.1514 0.0885 0.053 Uiso 1 1 calc R . .
C8 C 0.34636(12) 0.86030(13) 0.2805(2) 0.0414(5) Uani 1 1 d . . .
H8 H 0.3433 0.9126 0.3404 0.050 Uiso 1 1 calc R . .
C9 C 0.27369(12) 0.81028(13) 0.2522(3) 0.0433(5) Uani 1 1 d . . .
H9 H 0.2224 0.8292 0.2947 0.052 Uiso 1 1 calc R . .
C10 C 0.42669(12) 0.75478(13) 0.1288(3) 0.0439(5) Uani 1 1 d . . .
H10 H 0.4780 0.7356 0.0868 0.053 Uiso 1 1 calc R . .
C11 C 0.35383(13) 0.70568(14) 0.1005(3) 0.0463(6) Uani 1 1 d . . .
H11 H 0.3569 0.6538 0.0395 0.056 Uiso 1 1 calc R . .
C1 C 0.5000 1.1674(2) 0.2500 0.0473(8) Uani 1 2 d S . .
H1 H 0.5000 1.2305 0.2500 0.057 Uiso 1 2 calc SR . .
C14 C 0.18654(14) 0.61396(14) 0.0321(3) 0.0493(6) Uani 1 1 d . . .
H14 H 0.2321 0.5958 -0.0292 0.059 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0250(12) 0.0306(11) 0.0636(16) 0.000 -0.0111(11) 0.000
O1 0.0373(9) 0.0550(10) 0.0890(13) -0.0088(9) -0.0018(8) -0.0079(7)
O2 0.0463(9) 0.0565(10) 0.1032(14) -0.0213(10) -0.0063(10) -0.0154(8)
C12 0.0309(11) 0.0382(11) 0.0521(13) 0.0034(9) -0.0077(9) -0.0051(8)
C3 0.0336(10) 0.0394(11) 0.0437(12) -0.0019(9) -0.0072(9) 0.0020(8)
C4 0.0260(13) 0.0320(14) 0.0427(16) 0.000 0.0007(11) 0.000
C13 0.0304(11) 0.0405(11) 0.0607(14) 0.0041(10) -0.0048(9) -0.0038(9)
C7 0.0278(10) 0.0315(9) 0.0493(12) 0.0024(9) -0.0086(8) 0.0000(8)
C15 0.0388(12) 0.0367(11) 0.0637(14) 0.0026(11) -0.0111(11) -0.0062(9)
C2 0.0427(12) 0.0387(11) 0.0503(13) 0.0052(10) -0.0030(10) 0.0090(9)
C8 0.0320(11) 0.0403(11) 0.0520(13) -0.0068(9) -0.0070(9) 0.0004(9)
C9 0.0277(10) 0.0466(11) 0.0555(13) -0.0018(10) -0.0033(9) 0.0007(9)
C10 0.0299(10) 0.0394(11) 0.0623(14) -0.0064(10) -0.0007(9) -0.0002(9)
C11 0.0387(12) 0.0378(11) 0.0624(14) -0.0090(10) -0.0050(10) -0.0039(9)
C1 0.0494(18) 0.0327(15) 0.0596(19) 0.000 0.0007(15) 0.000
C14 0.0361(12) 0.0441(12) 0.0676(15) 0.0003(11) -0.0024(10) -0.0092(9)

_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 C4 1.420(3) . ?
N1 C7 1.421(2) 3_655 ?
N1 C7 1.421(2) . ?
O1 C15 1.250(3) . ?
O2 C15 1.292(3) . ?
O2 H2 0.8200 . ?
C12 C11 1.393(3) . ?
C12 C9 1.394(3) . ?
C12 C13 1.463(3) . ?
C3 C2 1.381(3) . ?
C3 C4 1.392(2) . ?
C3 H3 0.9300 . ?
C4 C3 1.392(2) 3_655 ?
C13 C14 1.327(3) . ?
C13 H13 0.9300 . ?
C7 C8 1.391(3) . ?
C7 C10 1.393(3) . ?
C15 C14 1.464(3) . ?
C2 C1 1.376(3) . ?
C2 H2A 0.9300 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C1 C2 1.376(3) 3_655 ?
C1 H1 0.9300 . ?
C14 H14 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
C4 N1 C7 120.50(11) . 3_655 ?
C4 N1 C7 120.50(11) . . ?
C7 N1 C7 119.0(2) 3_655 . ?
C15 O2 H2 109.5 . . ?
C11 C12 C9 117.55(18) . . ?
C11 C12 C13 122.37(19) . . ?
C9 C12 C13 120.08(18) . . ?
C2 C3 C4 120.18(19) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C3 118.7(2) . 3_655 ?
C3 C4 N1 120.67(12) . . ?
C3 C4 N1 120.67(12) 3_655 . ?
C14 C13 C12 127.2(2) . . ?
C14 C13 H13 116.4 . . ?
C12 C13 H13 116.4 . . ?
C8 C7 C10 118.62(17) . . ?
C8 C7 N1 121.57(17) . . ?
C10 C7 N1 119.81(17) . . ?
O1 C15 O2 123.39(19) . . ?
O1 C15 C14 121.2(2) . . ?
O2 C15 C14 115.4(2) . . ?
C1 C2 C3 121.0(2) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C9 C8 C7 120.41(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C12 121.39(19) . . ?
C8 C9 H9 119.3 . . ?
C12 C9 H9 119.3 . . ?
C11 C10 C7 120.54(19) . . ?
C11 C10 H10 119.7 . . ?
C7 C10 H10 119.7 . . ?
C10 C11 C12 121.48(19) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C2 C1 C2 118.9(3) 3_655 . ?
C2 C1 H1 120.5 3_655 . ?
C2 C1 H1 120.5 . . ?
C13 C14 C15 122.0(2) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?

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 C3 C4 C3 -0.29(14) . . . 3_655 ?
C2 C3 C4 N1 179.71(14) . . . . ?
C7 N1 C4 C3 147.49(13) 3_655 . . . ?
C7 N1 C4 C3 -32.51(13) . . . . ?
C7 N1 C4 C3 -32.51(13) 3_655 . . 3_655 ?
C7 N1 C4 C3 147.50(13) . . . 3_655 ?
C11 C12 C13 C14 -10.7(3) . . . . ?
C9 C12 C13 C14 169.3(2) . . . . ?
C4 N1 C7 C8 -40.6(2) . . . . ?
C7 N1 C7 C8 139.4(2) 3_655 . . . ?
C4 N1 C7 C10 140.10(15) . . . . ?
C7 N1 C7 C10 -39.90(15) 3_655 . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C10 C7 C8 C9 0.8(3) . . . . ?
N1 C7 C8 C9 -178.51(18) . . . . ?
C7 C8 C9 C12 -0.8(3) . . . . ?
C11 C12 C9 C8 0.3(3) . . . . ?
C13 C12 C9 C8 -179.64(19) . . . . ?
C8 C7 C10 C11 -0.4(3) . . . . ?
N1 C7 C10 C11 178.91(19) . . . . ?
C7 C10 C11 C12 0.0(3) . . . . ?
C9 C12 C11 C10 0.0(3) . . . . ?
C13 C12 C11 C10 -180.0(2) . . . . ?
C3 C2 C1 C2 -0.30(15) . . . 3_655 ?
C12 C13 C14 C15 179.96(19) . . . . ?
O1 C15 C14 C13 4.0(3) . . . . ?
O2 C15 C14 C13 -176.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.039
