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

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1037602'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;

_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
