# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_141025e
_database_code_depnum_ccdc_archive 'CCDC 1426678'
_audit_update_record             
;
2015-09-23 deposited with the CCDC.	2019-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Ocean University of China'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O4'
_chemical_formula_weight         288.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   14.1112(10)
_cell_length_b                   4.6513(3)
_cell_length_c                   21.1240(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.827(2)
_cell_angle_gamma                90.00
_cell_volume                     1366.14(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1185
_cell_measurement_theta_min      3.3000
_cell_measurement_theta_max      70.7420

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7715
_exptl_absorpt_correction_T_max  0.8896
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            3970
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         66.17
_reflns_number_total             2408
_reflns_number_gt                1732
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0556P)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     SHELXL
_refine_ls_extinction_coef       0.0049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2408
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.63813(15) 0.6491(5) 0.14135(9) 0.0405(6) Uani 1 1 d . . .
N8 N 0.72006(13) 0.4851(4) 0.30896(9) 0.0334(5) Uani 1 1 d . . .
O15 O 0.70537(11) 0.5046(4) 0.44529(8) 0.0385(5) Uani 1 1 d . . .
O19 O 0.87196(12) 0.4642(4) 0.46254(8) 0.0410(5) Uani 1 1 d . . .
O11A O 0.92032(12) 1.1032(4) 0.28159(8) 0.0434(5) Uani 1 1 d . . .
O17A O 0.79733(14) 0.6667(4) 0.57689(9) 0.0488(5) Uani 1 1 d . . .
H17A H 0.7520 0.7033 0.5952 0.073 Uiso 1 1 calc R . .
C2 C 0.5647(2) 0.5800(7) 0.09505(13) 0.0484(7) Uani 1 1 d . . .
H2 H 0.5620 0.6655 0.0550 0.058 Uiso 1 1 calc R . .
C3 C 0.49288(19) 0.3900(6) 0.10303(13) 0.0463(7) Uani 1 1 d . . .
H3 H 0.4423 0.3525 0.0697 0.056 Uiso 1 1 calc R . .
C4 C 0.49793(18) 0.2577(6) 0.16139(12) 0.0447(7) Uani 1 1 d . . .
H4 H 0.4517 0.1239 0.1681 0.054 Uiso 1 1 calc R . .
C5 C 0.57295(18) 0.3264(6) 0.21016(12) 0.0420(7) Uani 1 1 d . . .
H5 H 0.5777 0.2387 0.2501 0.050 Uiso 1 1 calc R . .
C6 C 0.64092(16) 0.5265(5) 0.19919(11) 0.0324(6) Uani 1 1 d . . .
C7 C 0.71955(16) 0.6175(5) 0.25210(11) 0.0327(6) Uani 1 1 d . . .
C9 C 0.78880(16) 0.5628(5) 0.35710(11) 0.0334(6) Uani 1 1 d . . .
C10 C 0.85967(17) 0.7640(5) 0.35229(11) 0.0346(6) Uani 1 1 d . . .
H10 H 0.9074 0.8059 0.3872 0.041 Uiso 1 1 calc R . .
C11 C 0.85699(16) 0.8998(5) 0.29402(11) 0.0333(6) Uani 1 1 d . . .
C12 C 0.78495(17) 0.8269(5) 0.24295(11) 0.0357(6) Uani 1 1 d . . .
H12 H 0.7810 0.9178 0.2034 0.043 Uiso 1 1 calc R . .
C13 C 1.00238(18) 1.1571(7) 0.33048(13) 0.0486(7) Uani 1 1 d . . .
H13A H 0.9812 1.2095 0.3697 0.073 Uiso 1 1 calc R . .
H13B H 1.0397 1.3111 0.3171 0.073 Uiso 1 1 calc R . .
H13C H 1.0412 0.9867 0.3373 0.073 Uiso 1 1 calc R . .
C14 C 0.78646(17) 0.4101(6) 0.41990(11) 0.0349(6) Uani 1 1 d . . .
H14 H 0.7808 0.2028 0.4119 0.042 Uiso 1 1 calc R . .
C16 C 0.69888(18) 0.3435(6) 0.50208(12) 0.0415(7) Uani 1 1 d . . .
H16A H 0.6907 0.1414 0.4912 0.050 Uiso 1 1 calc R . .
H16B H 0.6429 0.4062 0.5194 0.050 Uiso 1 1 calc R . .
C17 C 0.78789(18) 0.3816(6) 0.55245(11) 0.0383(6) Uani 1 1 d . . .
H17 H 0.7852 0.2478 0.5879 0.046 Uiso 1 1 calc R . .
C18 C 0.87497(19) 0.3127(6) 0.52232(12) 0.0438(7) Uani 1 1 d . . .
H18A H 0.9328 0.3661 0.5517 0.053 Uiso 1 1 calc R . .
H18B H 0.8773 0.1074 0.5147 0.053 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
N1 C2 1.337(3) . ?
N1 C6 1.343(3) . ?
N8 C9 1.330(3) . ?
N8 C7 1.349(3) . ?
O15 C14 1.414(3) . ?
O15 C16 1.430(3) . ?
O19 C14 1.400(3) . ?
O19 C18 1.440(3) . ?
O11A C11 1.357(3) . ?
O11A C13 1.436(3) . ?
O17A C17 1.421(3) . ?
O17A H17A 0.8200 . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(3) . ?
C7 C12 1.378(3) . ?
C9 C10 1.386(3) . ?
C9 C14 1.510(3) . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9800 . ?
C16 C17 1.512(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.511(3) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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 N1 C6 117.5(2) . . ?
C9 N8 C7 116.7(2) . . ?
C14 O15 C16 109.09(18) . . ?
C14 O19 C18 111.69(19) . . ?
C11 O11A C13 117.4(2) . . ?
C17 O17A H17A 109.5 . . ?
N1 C2 C3 124.0(3) . . ?
N1 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C4 C3 C2 118.2(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C5 121.6(2) . . ?
N1 C6 C7 117.6(2) . . ?
C5 C6 C7 120.8(2) . . ?
N8 C7 C12 123.1(2) . . ?
N8 C7 C6 115.3(2) . . ?
C12 C7 C6 121.6(2) . . ?
N8 C9 C10 124.6(2) . . ?
N8 C9 C14 114.9(2) . . ?
C10 C9 C14 120.4(2) . . ?
C11 C10 C9 117.7(2) . . ?
C11 C10 H10 121.2 . . ?
C9 C10 H10 121.2 . . ?
O11A C11 C10 125.0(2) . . ?
O11A C11 C12 116.0(2) . . ?
C10 C11 C12 119.0(2) . . ?
C7 C12 C11 118.8(2) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
O11A C13 H13A 109.5 . . ?
O11A C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O11A C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O19 C14 O15 111.38(18) . . ?
O19 C14 C9 109.6(2) . . ?
O15 C14 C9 109.11(19) . . ?
O19 C14 H14 108.9 . . ?
O15 C14 H14 108.9 . . ?
C9 C14 H14 108.9 . . ?
O15 C16 C17 111.4(2) . . ?
O15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
O15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O17A C17 C18 108.5(2) . . ?
O17A C17 C16 112.3(2) . . ?
C18 C17 C16 108.4(2) . . ?
O17A C17 H17 109.2 . . ?
C18 C17 H17 109.2 . . ?
C16 C17 H17 109.2 . . ?
O19 C18 C17 111.2(2) . . ?
O19 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
O19 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?

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
C6 N1 C2 C3 -0.6(4) . . . . ?
N1 C2 C3 C4 -1.7(5) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C2 N1 C6 C5 2.7(4) . . . . ?
C2 N1 C6 C7 -176.3(2) . . . . ?
C4 C5 C6 N1 -2.5(4) . . . . ?
C4 C5 C6 C7 176.4(2) . . . . ?
C9 N8 C7 C12 -1.0(3) . . . . ?
C9 N8 C7 C6 -179.6(2) . . . . ?
N1 C6 C7 N8 -179.1(2) . . . . ?
C5 C6 C7 N8 1.9(3) . . . . ?
N1 C6 C7 C12 2.3(3) . . . . ?
C5 C6 C7 C12 -176.7(2) . . . . ?
C7 N8 C9 C10 -1.2(3) . . . . ?
C7 N8 C9 C14 179.8(2) . . . . ?
N8 C9 C10 C11 2.1(4) . . . . ?
C14 C9 C10 C11 -178.9(2) . . . . ?
C13 O11A C11 C10 7.5(4) . . . . ?
C13 O11A C11 C12 -172.3(2) . . . . ?
C9 C10 C11 O11A 179.4(2) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
N8 C7 C12 C11 2.1(4) . . . . ?
C6 C7 C12 C11 -179.4(2) . . . . ?
O11A C11 C12 C7 178.7(2) . . . . ?
C10 C11 C12 C7 -1.1(4) . . . . ?
C18 O19 C14 O15 61.7(3) . . . . ?
C18 O19 C14 C9 -177.51(19) . . . . ?
C16 O15 C14 O19 -63.5(3) . . . . ?
C16 O15 C14 C9 175.44(19) . . . . ?
N8 C9 C14 O19 167.97(19) . . . . ?
C10 C9 C14 O19 -11.1(3) . . . . ?
N8 C9 C14 O15 -69.8(3) . . . . ?
C10 C9 C14 O15 111.1(2) . . . . ?
C14 O15 C16 C17 59.6(3) . . . . ?
O15 C16 C17 O17A 66.9(3) . . . . ?
O15 C16 C17 C18 -53.1(3) . . . . ?
C14 O19 C18 C17 -54.9(3) . . . . ?
O17A C17 C18 O19 -72.5(3) . . . . ?
C16 C17 C18 O19 49.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.17
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
