# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1431202'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O4'
_chemical_formula_weight         310.30

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   12.9877(3)
_cell_length_b                   7.4549(2)
_cell_length_c                   31.4842(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3048.36(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9912
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'bruker Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17171
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2679
_reflns_number_gt                2003
_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)+(0.1281P)²+5.9330P] 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         2679
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2703
_refine_ls_wR_factor_gt          0.2516
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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 0.6641(6) 0.2835(9) 0.49096(18) 0.0879(18) Uani 1 1 d . . .
H1 H 0.6990 0.3376 0.4686 0.106 Uiso 1 1 calc R . .
C2 C 0.5589(6) 0.2812(9) 0.4914(2) 0.096(2) Uani 1 1 d . . .
H2 H 0.5220 0.3313 0.4690 0.115 Uiso 1 1 calc R . .
C3 C 0.5086(5) 0.2055(9) 0.5245(2) 0.0891(19) Uani 1 1 d . . .
H3 H 0.4370 0.2032 0.5246 0.107 Uiso 1 1 calc R . .
C4 C 0.5619(4) 0.1319(7) 0.55808(16) 0.0627(13) Uani 1 1 d . . .
H4 H 0.5265 0.0833 0.5810 0.075 Uiso 1 1 calc R . .
C5 C 0.6684(3) 0.1307(5) 0.55754(13) 0.0446(10) Uani 1 1 d . . .
C6 C 0.7185(4) 0.2059(8) 0.52363(15) 0.0715(15) Uani 1 1 d . . .
H6 H 0.7901 0.2045 0.5227 0.086 Uiso 1 1 calc R . .
C7 C 0.7244(3) 0.0511(5) 0.59297(12) 0.0374(9) Uani 1 1 d . . .
C8 C 0.8603(3) -0.0144(5) 0.63025(12) 0.0416(9) Uani 1 1 d . . .
C9 C 0.7756(3) -0.0783(6) 0.64921(13) 0.0472(10) Uani 1 1 d . . .
H9 H 0.7745 -0.1422 0.6746 0.057 Uiso 1 1 calc R . .
C10 C 0.9713(3) -0.0167(6) 0.64023(14) 0.0481(10) Uani 1 1 d . . .
H10A H 1.0091 -0.0470 0.6147 0.058 Uiso 1 1 calc R . .
H10B H 0.9842 -0.1101 0.6610 0.058 Uiso 1 1 calc R . .
C11 C 1.0123(3) 0.1614(5) 0.65758(12) 0.0394(9) Uani 1 1 d . . .
H11 H 0.9722 0.1954 0.6827 0.047 Uiso 1 1 calc R . .
C12 C 1.1247(3) 0.1401(5) 0.67016(14) 0.0449(10) Uani 1 1 d . . .
C13 C 1.1999(3) 0.1699(7) 0.63825(17) 0.0622(13) Uani 1 1 d . . .
H13 H 1.1786 0.2023 0.6111 0.075 Uiso 1 1 calc R . .
C14 C 1.3024(4) 0.1524(8) 0.6463(2) 0.0770(16) Uani 1 1 d . . .
H14 H 1.3502 0.1730 0.6248 0.092 Uiso 1 1 calc R . .
C15 C 1.3352(4) 0.1045(7) 0.6861(2) 0.0719(16) Uani 1 1 d . . .
H15 H 1.4053 0.0901 0.6911 0.086 Uiso 1 1 calc R . .
C16 C 1.2686(4) 0.0780(7) 0.7181(2) 0.0678(14) Uani 1 1 d . . .
H16 H 1.2918 0.0503 0.7453 0.081 Uiso 1 1 calc R . .
C17 C 1.1629(3) 0.0931(6) 0.70948(15) 0.0559(12) Uani 1 1 d . . .
N1 N 0.6892(2) -0.0344(5) 0.62501(11) 0.0442(8) Uani 1 1 d . . .
N2 N 1.0933(4) 0.0585(7) 0.74395(13) 0.0744(13) Uani 1 1 d . . .
O1 O 0.82867(18) 0.0692(4) 0.59351(8) 0.0405(7) Uani 1 1 d . . .
O2 O 1.0125(4) -0.0185(7) 0.73737(12) 0.1013(15) Uani 1 1 d . . .
O3 O 1.1185(4) 0.1041(10) 0.77999(14) 0.137(2) Uani 1 1 d . . .
O4 O 1.0063(2) 0.3004(5) 0.62725(12) 0.0691(10) Uani 1 1 d . . .
H4A H 0.9474 0.3400 0.6266 0.104 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
C1 0.109(5) 0.093(5) 0.061(3) 0.018(3) -0.016(3) 0.001(4)
C2 0.127(6) 0.080(4) 0.080(4) 0.005(3) -0.051(4) 0.023(4)
C3 0.065(3) 0.097(5) 0.105(5) 0.007(4) -0.039(3) 0.015(3)
C4 0.048(3) 0.066(3) 0.074(3) 0.003(3) -0.016(2) 0.002(2)
C5 0.043(2) 0.038(2) 0.053(2) -0.0091(19) -0.0135(18) -0.0002(17)
C6 0.069(3) 0.090(4) 0.056(3) 0.010(3) -0.008(2) -0.003(3)
C7 0.0319(19) 0.0349(19) 0.045(2) -0.0105(17) -0.0017(15) -0.0049(15)
C8 0.040(2) 0.037(2) 0.048(2) -0.0082(18) -0.0071(17) 0.0000(17)
C9 0.050(2) 0.045(2) 0.046(2) 0.0003(19) -0.0054(18) -0.0029(19)
C10 0.035(2) 0.048(2) 0.062(3) -0.010(2) -0.0073(18) 0.0053(18)
C11 0.0327(19) 0.039(2) 0.047(2) 0.0009(17) -0.0025(16) 0.0017(16)
C12 0.035(2) 0.039(2) 0.061(3) -0.0062(19) -0.0096(18) 0.0011(17)
C13 0.041(2) 0.068(3) 0.078(3) 0.009(3) -0.003(2) -0.006(2)
C14 0.044(3) 0.073(4) 0.114(5) 0.002(3) 0.010(3) -0.003(3)
C15 0.048(3) 0.058(3) 0.111(4) 0.001(3) -0.023(3) 0.006(2)
C16 0.046(3) 0.055(3) 0.102(4) -0.002(3) -0.024(3) 0.000(2)
C17 0.052(3) 0.053(3) 0.062(3) -0.003(2) -0.011(2) -0.001(2)
N1 0.0359(17) 0.0441(19) 0.0525(19) -0.0041(16) -0.0012(15) -0.0075(15)
N2 0.060(3) 0.105(4) 0.058(3) -0.005(2) -0.011(2) 0.002(3)
O1 0.0318(13) 0.0446(15) 0.0450(15) -0.0041(12) -0.0022(11) -0.0052(11)
O2 0.088(3) 0.141(4) 0.075(3) 0.008(3) 0.011(2) -0.032(3)
O3 0.115(4) 0.230(7) 0.066(3) -0.014(4) -0.026(3) 0.006(4)
O4 0.0430(17) 0.069(2) 0.096(3) 0.018(2) -0.0075(17) 0.0036(16)

_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 1.367(10) . ?
C1 C6 1.375(7) . ?
C2 C3 1.354(9) . ?
C3 C4 1.377(7) . ?
C4 C5 1.383(6) . ?
C5 C6 1.371(6) . ?
C5 C7 1.458(5) . ?
C7 N1 1.278(5) . ?
C7 O1 1.361(4) . ?
C8 C9 1.339(6) . ?
C8 O1 1.376(5) . ?
C8 C10 1.475(5) . ?
C9 N1 1.394(5) . ?
C10 C11 1.531(6) . ?
C11 O4 1.411(5) . ?
C11 C12 1.521(5) . ?
C12 C17 1.379(6) . ?
C12 C13 1.419(6) . ?
C13 C14 1.362(6) . ?
C14 C15 1.371(8) . ?
C15 C16 1.342(8) . ?
C16 C17 1.404(6) . ?
C17 N2 1.435(6) . ?
N2 O2 1.214(6) . ?
N2 O3 1.229(6) . ?

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 120.1(6) . . ?
C3 C2 C1 119.6(5) . . ?
C2 C3 C4 121.0(6) . . ?
C3 C4 C5 119.7(5) . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 C7 121.7(4) . . ?
C4 C5 C7 119.5(4) . . ?
C5 C6 C1 120.7(5) . . ?
N1 C7 O1 113.3(3) . . ?
N1 C7 C5 129.0(3) . . ?
O1 C7 C5 117.8(3) . . ?
C9 C8 O1 106.9(3) . . ?
C9 C8 C10 134.7(4) . . ?
O1 C8 C10 118.4(4) . . ?
C8 C9 N1 109.5(4) . . ?
C8 C10 C11 113.9(3) . . ?
O4 C11 C12 107.8(3) . . ?
O4 C11 C10 112.1(3) . . ?
C12 C11 C10 109.6(3) . . ?
C17 C12 C13 115.3(4) . . ?
C17 C12 C11 127.3(4) . . ?
C13 C12 C11 117.4(4) . . ?
C14 C13 C12 121.7(5) . . ?
C13 C14 C15 119.9(5) . . ?
C16 C15 C14 121.6(5) . . ?
C15 C16 C17 118.3(5) . . ?
C12 C17 C16 123.1(5) . . ?
C12 C17 N2 119.9(4) . . ?
C16 C17 N2 117.0(4) . . ?
C7 N1 C9 105.1(3) . . ?
O2 N2 O3 121.2(5) . . ?
O2 N2 C17 120.0(4) . . ?
O3 N2 C17 118.8(5) . . ?
C7 O1 C8 105.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.067
