# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

 
data_shelxl 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C18 H16 N2 O3, C H4 O'  
_chemical_formula_sum 
 'C19 H20 N2 O4' 
_chemical_formula_weight          340.37 
 
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    'P 21/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                    7.5360(15) 
_cell_length_b                    15.774(3) 
_cell_length_c                    14.325(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  101.14(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1670.7(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     4254 
_cell_measurement_theta_min       3.0 
_cell_measurement_theta_max       29.0
 
_exptl_crystal_description        needle 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.23 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.14 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.353 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              720 
_exptl_absorpt_coefficient_mu     0.096 
_exptl_absorpt_correction_type    numerical 
_exptl_absorpt_correction_T_min   0.9783 
_exptl_absorpt_correction_T_max   0.9867 
_exptl_absorpt_process_details    'NUMABS (Rigaku, 1999)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'MicroMax003_Mo'  
_diffrn_radiation_monochromator   Confocal  
_diffrn_measurement_device_type  'Rigaku Saturn724' 
_diffrn_measurement_method        'ω scans'  
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             22291 
_diffrn_reflns_av_R_equivalents   0.1091 
_diffrn_reflns_av_sigmaI/netI     0.0891 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -21 
_diffrn_reflns_limit_k_max        21 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          3.04 
_diffrn_reflns_theta_max          29.04 
_reflns_number_total              4454 
_reflns_number_gt                 2982 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)'
_computing_cell_refinement        'CrystalClear-SM Expert 2.1 b24' 
_computing_data_reduction         'CrystalClear-SM Expert 2.1 b24'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_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)+(0.0835P)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     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4454 
_refine_ls_number_parameters      242 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1140 
_refine_ls_R_factor_gt            0.0727 
_refine_ls_wR_factor_ref          0.2026 
_refine_ls_wR_factor_gt           0.1632 
_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 
O1 O 0.0668(2) 0.58728(10) 0.07942(11) 0.0277(4) Uani 1 1 d . . . 
N1 N 0.4915(3) 0.80888(11) 0.48905(12) 0.0193(4) Uani 1 1 d . . . 
H1A H 0.5167 0.8411 0.5401 0.023 Uiso 1 1 calc R . . 
C1 C 0.5389(3) 0.72640(14) 0.48356(15) 0.0188(5) Uani 1 1 d . . . 
O2 O 0.0056(2) 0.70027(10) -0.02452(11) 0.0274(4) Uani 1 1 d . . . 
N2 N 0.4803(3) 0.69704(11) 0.39608(12) 0.0203(4) Uani 1 1 d . . . 
C2 C 0.3920(3) 0.76420(14) 0.34344(15) 0.0193(5) Uani 1 1 d . . . 
O3 O 0.4117(2) 1.06928(9) 0.36887(11) 0.0248(4) Uani 1 1 d . . . 
H3A H 0.3782 1.0826 0.3114 0.037 Uiso 1 1 calc R . . 
C3 C 0.3971(3) 0.83373(14) 0.40119(15) 0.0187(5) Uani 1 1 d . . . 
O4 O 0.6762(3) 0.58374(12) 0.31565(12) 0.0294(4) Uani 1 1 d . . . 
H4A H 0.605(6) 0.621(2) 0.342(3) 0.098(14) Uiso 1 1 d . . . 
C4 C 0.6378(3) 0.67641(14) 0.56317(15) 0.0200(5) Uani 1 1 d . . . 
C5 C 0.7191(3) 0.71395(15) 0.64886(15) 0.0227(5) Uani 1 1 d . . . 
H5A H 0.7136 0.7737 0.6563 0.027 Uiso 1 1 calc R . . 
C6 C 0.8084(3) 0.66408(16) 0.72380(16) 0.0266(5) Uani 1 1 d . . . 
H6A H 0.8640 0.6899 0.7821 0.032 Uiso 1 1 calc R . . 
C7 C 0.8162(3) 0.57716(15) 0.71334(16) 0.0254(5) Uani 1 1 d . . . 
H7A H 0.8772 0.5432 0.7644 0.030 Uiso 1 1 calc R . . 
C8 C 0.7352(4) 0.53945(15) 0.62847(16) 0.0263(5) Uani 1 1 d . . . 
H8A H 0.7398 0.4796 0.6215 0.032 Uiso 1 1 calc R . . 
C9 C 0.6473(3) 0.58884(15) 0.55376(16) 0.0238(5) Uani 1 1 d . . . 
H9A H 0.5930 0.5627 0.4955 0.029 Uiso 1 1 calc R . . 
C10 C 0.2992(3) 0.75197(15) 0.24417(16) 0.0208(5) Uani 1 1 d . . . 
C11 C 0.2352(3) 0.67007(14) 0.21496(15) 0.0217(5) Uani 1 1 d . . . 
H11A H 0.2584 0.6229 0.2568 0.026 Uiso 1 1 calc R . . 
C12 C 0.1388(3) 0.66118(14) 0.12425(16) 0.0214(5) Uani 1 1 d . . . 
C13 C 0.1041(3) 0.72831(15) 0.06204(16) 0.0229(5) Uani 1 1 d . . . 
C14 C 0.1704(3) 0.80814(15) 0.08597(16) 0.0247(5) Uani 1 1 d . . . 
H14A H 0.1505 0.8539 0.0420 0.030 Uiso 1 1 calc R . . 
C15 C 0.2693(3) 0.81842(15) 0.17892(16) 0.0227(5) Uani 1 1 d . . . 
H15A H 0.3176 0.8727 0.1981 0.027 Uiso 1 1 calc R . . 
C16 C 0.3266(3) 0.92207(14) 0.38621(15) 0.0204(5) Uani 1 1 d . . . 
H16A H 0.2725 0.9392 0.4410 0.025 Uiso 1 1 calc R . . 
H16B H 0.2305 0.9240 0.3284 0.025 Uiso 1 1 calc R . . 
C17 C 0.4765(3) 0.98429(14) 0.37531(16) 0.0223(5) Uani 1 1 d . . . 
H17A H 0.5774 0.9790 0.4306 0.027 Uiso 1 1 calc R . . 
H17B H 0.5235 0.9701 0.3173 0.027 Uiso 1 1 calc R . . 
C18 C -0.0567(3) 0.61761(15) -0.00320(16) 0.0269(6) Uani 1 1 d . . . 
H18B H -0.0579 0.5788 -0.0576 0.032 Uiso 1 1 calc R . . 
H18A H -0.1808 0.6212 0.0099 0.032 Uiso 1 1 calc R . . 
C20 C 0.8621(4) 0.6006(2) 0.3555(2) 0.0394(7) Uani 1 1 d . . . 
H20A H 0.883(5) 0.662(2) 0.388(2) 0.071(11) Uiso 1 1 d . . . 
H20C H 0.897(5) 0.562(2) 0.406(3) 0.071(11) Uiso 1 1 d . . . 
H20B H 0.926(7) 0.587(3) 0.306(3) 0.127(17) Uiso 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 
O1 C12 1.390(3) . ? 
O1 C18 1.439(3) . ? 
N1 C1 1.355(3) . ? 
N1 C3 1.378(3) . ? 
N1 H1A 0.8800 . ? 
C1 N2 1.329(3) . ? 
C1 C4 1.466(3) . ? 
O2 C13 1.389(3) . ? 
O2 C18 1.438(3) . ? 
N2 C2 1.393(3) . ? 
C2 C3 1.370(3) . ? 
C2 C10 1.471(3) . ? 
O3 C17 1.424(3) . ? 
O3 H3A 0.8400 . ? 
C3 C16 1.492(3) . ? 
O4 C20 1.432(3) . ? 
O4 H4A 0.93(4) . ? 
C4 C9 1.391(3) . ? 
C4 C5 1.394(3) . ? 
C5 C6 1.395(3) . ? 
C5 H5A 0.9500 . ? 
C6 C7 1.382(3) . ? 
C6 H6A 0.9500 . ? 
C7 C8 1.385(3) . ? 
C7 H7A 0.9500 . ? 
C8 C9 1.384(3) . ? 
C8 H8A 0.9500 . ? 
C9 H9A 0.9500 . ? 
C10 C15 1.394(3) . ? 
C10 C11 1.414(3) . ? 
C11 C12 1.368(3) . ? 
C11 H11A 0.9500 . ? 
C12 C13 1.376(3) . ? 
C13 C14 1.374(3) . ? 
C14 C15 1.404(3) . ? 
C14 H14A 0.9500 . ? 
C15 H15A 0.9500 . ? 
C16 C17 1.527(3) . ? 
C16 H16A 0.9900 . ? 
C16 H16B 0.9900 . ? 
C17 H17A 0.9900 . ? 
C17 H17B 0.9900 . ? 
C18 H18B 0.9900 . ? 
C18 H18A 0.9900 . ? 
C20 H20A 1.07(4) . ? 
C20 H20C 0.94(4) . ? 
C20 H20B 0.96(5) . ? 
 
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 
C12 O1 C18 103.53(17) . . ? 
C1 N1 C3 108.39(18) . . ? 
C1 N1 H1A 125.8 . . ? 
C3 N1 H1A 125.8 . . ? 
N2 C1 N1 110.25(19) . . ? 
N2 C1 C4 124.9(2) . . ? 
N1 C1 C4 124.84(19) . . ? 
C13 O2 C18 103.83(17) . . ? 
C1 N2 C2 106.39(18) . . ? 
C3 C2 N2 109.11(19) . . ? 
C3 C2 C10 129.9(2) . . ? 
N2 C2 C10 120.77(19) . . ? 
C17 O3 H3A 109.5 . . ? 
C2 C3 N1 105.86(19) . . ? 
C2 C3 C16 133.9(2) . . ? 
N1 C3 C16 120.25(19) . . ? 
C20 O4 H4A 108(3) . . ? 
C9 C4 C5 119.0(2) . . ? 
C9 C4 C1 119.1(2) . . ? 
C5 C4 C1 121.8(2) . . ? 
C4 C5 C6 120.2(2) . . ? 
C4 C5 H5A 119.9 . . ? 
C6 C5 H5A 119.9 . . ? 
C7 C6 C5 120.0(2) . . ? 
C7 C6 H6A 120.0 . . ? 
C5 C6 H6A 120.0 . . ? 
C6 C7 C8 120.0(2) . . ? 
C6 C7 H7A 120.0 . . ? 
C8 C7 H7A 120.0 . . ? 
C9 C8 C7 120.0(2) . . ? 
C9 C8 H8A 120.0 . . ? 
C7 C8 H8A 120.0 . . ? 
C8 C9 C4 120.7(2) . . ? 
C8 C9 H9A 119.7 . . ? 
C4 C9 H9A 119.7 . . ? 
C15 C10 C11 119.2(2) . . ? 
C15 C10 C2 122.3(2) . . ? 
C11 C10 C2 118.5(2) . . ? 
C12 C11 C10 117.6(2) . . ? 
C12 C11 H11A 121.2 . . ? 
C10 C11 H11A 121.2 . . ? 
C11 C12 C13 122.4(2) . . ? 
C11 C12 O1 127.8(2) . . ? 
C13 C12 O1 109.7(2) . . ? 
C14 C13 C12 122.0(2) . . ? 
C14 C13 O2 128.4(2) . . ? 
C12 C13 O2 109.6(2) . . ? 
C13 C14 C15 116.3(2) . . ? 
C13 C14 H14A 121.8 . . ? 
C15 C14 H14A 121.8 . . ? 
C10 C15 C14 122.5(2) . . ? 
C10 C15 H15A 118.8 . . ? 
C14 C15 H15A 118.8 . . ? 
C3 C16 C17 111.41(19) . . ? 
C3 C16 H16A 109.3 . . ? 
C17 C16 H16A 109.3 . . ? 
C3 C16 H16B 109.3 . . ? 
C17 C16 H16B 109.3 . . ? 
H16A C16 H16B 108.0 . . ? 
O3 C17 C16 111.13(19) . . ? 
O3 C17 H17A 109.4 . . ? 
C16 C17 H17A 109.4 . . ? 
O3 C17 H17B 109.4 . . ? 
C16 C17 H17B 109.4 . . ? 
H17A C17 H17B 108.0 . . ? 
O2 C18 O1 106.89(18) . . ? 
O2 C18 H18B 110.3 . . ? 
O1 C18 H18B 110.3 . . ? 
O2 C18 H18A 110.3 . . ? 
O1 C18 H18A 110.3 . . ? 
H18B C18 H18A 108.6 . . ? 
O4 C20 H20A 113.1(19) . . ? 
O4 C20 H20C 107(2) . . ? 
H20A C20 H20C 105(3) . . ? 
O4 C20 H20B 105(3) . . ? 
H20A C20 H20B 118(3) . . ? 
H20C C20 H20B 109(3) . . ? 
 
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 
C3 N1 C1 N2 0.4(3) . . . . ? 
C3 N1 C1 C4 -178.7(2) . . . . ? 
N1 C1 N2 C2 0.2(2) . . . . ? 
C4 C1 N2 C2 179.2(2) . . . . ? 
C1 N2 C2 C3 -0.7(2) . . . . ? 
C1 N2 C2 C10 -175.8(2) . . . . ? 
N2 C2 C3 N1 0.9(3) . . . . ? 
C10 C2 C3 N1 175.5(2) . . . . ? 
N2 C2 C3 C16 -179.6(2) . . . . ? 
C10 C2 C3 C16 -5.0(4) . . . . ? 
C1 N1 C3 C2 -0.8(2) . . . . ? 
C1 N1 C3 C16 179.67(19) . . . . ? 
N2 C1 C4 C9 -11.4(3) . . . . ? 
N1 C1 C4 C9 167.4(2) . . . . ? 
N2 C1 C4 C5 170.1(2) . . . . ? 
N1 C1 C4 C5 -11.1(3) . . . . ? 
C9 C4 C5 C6 0.0(3) . . . . ? 
C1 C4 C5 C6 178.5(2) . . . . ? 
C4 C5 C6 C7 -0.2(4) . . . . ? 
C5 C6 C7 C8 0.0(4) . . . . ? 
C6 C7 C8 C9 0.4(4) . . . . ? 
C7 C8 C9 C4 -0.6(4) . . . . ? 
C5 C4 C9 C8 0.4(3) . . . . ? 
C1 C4 C9 C8 -178.1(2) . . . . ? 
C3 C2 C10 C15 30.5(4) . . . . ? 
N2 C2 C10 C15 -155.4(2) . . . . ? 
C3 C2 C10 C11 -148.1(2) . . . . ? 
N2 C2 C10 C11 25.9(3) . . . . ? 
C15 C10 C11 C12 -3.0(3) . . . . ? 
C2 C10 C11 C12 175.7(2) . . . . ? 
C10 C11 C12 C13 0.3(3) . . . . ? 
C10 C11 C12 O1 178.3(2) . . . . ? 
C18 O1 C12 C11 165.8(2) . . . . ? 
C18 O1 C12 C13 -16.1(2) . . . . ? 
C11 C12 C13 C14 2.6(4) . . . . ? 
O1 C12 C13 C14 -175.7(2) . . . . ? 
C11 C12 C13 O2 179.41(19) . . . . ? 
O1 C12 C13 O2 1.1(3) . . . . ? 
C18 O2 C13 C14 -169.1(2) . . . . ? 
C18 O2 C13 C12 14.4(2) . . . . ? 
C12 C13 C14 C15 -2.6(3) . . . . ? 
O2 C13 C14 C15 -178.8(2) . . . . ? 
C11 C10 C15 C14 3.0(3) . . . . ? 
C2 C10 C15 C14 -175.7(2) . . . . ? 
C13 C14 C15 C10 -0.1(3) . . . . ? 
C2 C3 C16 C17 -101.6(3) . . . . ? 
N1 C3 C16 C17 77.9(3) . . . . ? 
C3 C16 C17 O3 -175.22(17) . . . . ? 
C13 O2 C18 O1 -24.2(2) . . . . ? 
C12 O1 C18 O2 24.8(2) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              25.50 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.319 
_refine_diff_density_min   -0.351 
_refine_diff_density_rms    0.081 
