# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_170617b
_database_code_depnum_ccdc_archive 'CCDC 1559727'
_audit_update_record             
;
2017-07-02 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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'

_cell_length_a                   7.9730(3)
_cell_length_b                   12.9128(5)
_cell_length_c                   14.3781(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1480.28(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1647
_cell_measurement_theta_min      4.5700
_cell_measurement_theta_max      70.7850

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7752
_exptl_absorpt_correction_T_max  0.9069
_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            3269
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.60
_diffrn_reflns_theta_max         66.05
_reflns_number_total             2197
_reflns_number_gt                2023
_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)+(0.0578P)²+0.1128P] 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       0.056(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration R
_refine_ls_number_reflns         2197
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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 1.0970(4) -0.08275(17) 0.74136(19) 0.0735(7) Uani 1 1 d . . .
O1 O 0.9700(2) 0.20614(15) 0.62117(11) 0.0558(5) Uani 1 1 d . . .
O2 O 1.2435(2) 0.2068(2) 0.61096(14) 0.0800(6) Uani 1 1 d . . .
O3 O 0.5374(2) 0.12542(17) 0.78649(15) 0.0701(6) Uani 1 1 d . . .
O4 O 0.7038(2) -0.00186(13) 0.83760(15) 0.0652(6) Uani 1 1 d . . .
C1 C 1.1256(3) 0.19693(18) 0.66061(18) 0.0512(6) Uani 1 1 d . . .
C2 C 1.1290(3) 0.17984(17) 0.76240(16) 0.0448(5) Uani 1 1 d . . .
H2A H 1.1095 0.2454 0.7936 0.054 Uiso 1 1 calc R . .
H2B H 1.2397 0.1558 0.7801 0.054 Uiso 1 1 calc R . .
C3 C 0.9972(3) 0.10054(16) 0.79629(15) 0.0401(5) Uani 1 1 d . . .
C4 C 0.8301(3) 0.12579(15) 0.74942(15) 0.0406(5) Uani 1 1 d . . .
C5 C 0.8258(3) 0.17817(17) 0.66960(17) 0.0472(5) Uani 1 1 d . . .
C6 C 0.6771(4) 0.2131(2) 0.6150(2) 0.0704(8) Uani 1 1 d . . .
H6A H 0.5763 0.1933 0.6469 0.106 Uiso 1 1 calc R . .
H6B H 0.6792 0.1813 0.5546 0.106 Uiso 1 1 calc R . .
H6C H 0.6801 0.2870 0.6083 0.106 Uiso 1 1 calc R . .
C7 C 0.9882(3) 0.10840(17) 0.90334(16) 0.0453(5) Uani 1 1 d . . .
C8 C 0.9126(4) 0.19456(19) 0.94200(18) 0.0575(6) Uani 1 1 d . . .
H8 H 0.8639 0.2443 0.9038 0.069 Uiso 1 1 calc R . .
C9 C 0.9095(5) 0.2068(3) 1.0373(2) 0.0787(9) Uani 1 1 d . . .
H9 H 0.8577 0.2646 1.0630 0.094 Uiso 1 1 calc R . .
C10 C 0.9815(5) 0.1349(3) 1.0946(2) 0.0892(11) Uani 1 1 d . . .
H10 H 0.9800 0.1442 1.1588 0.107 Uiso 1 1 calc R . .
C11 C 1.0564(5) 0.0488(3) 1.0566(2) 0.0847(10) Uani 1 1 d . . .
H11 H 1.1045 -0.0006 1.0955 0.102 Uiso 1 1 calc R . .
C12 C 1.0610(3) 0.0347(2) 0.96092(19) 0.0634(7) Uani 1 1 d . . .
H12 H 1.1123 -0.0236 0.9356 0.076 Uiso 1 1 calc R . .
C13 C 1.0517(3) -0.00428(19) 0.76677(16) 0.0481(6) Uani 1 1 d . . .
C14 C 0.6732(3) 0.08614(18) 0.79175(18) 0.0494(6) Uani 1 1 d . . .
C15 C 0.5665(4) -0.0446(2) 0.8935(3) 0.0908(12) Uani 1 1 d . . .
H15A H 0.5850 -0.1181 0.9026 0.109 Uiso 1 1 calc R . .
H15B H 0.4617 -0.0361 0.8601 0.109 Uiso 1 1 calc R . .
C16 C 0.5536(5) 0.0068(3) 0.9848(3) 0.1069(14) Uani 1 1 d . . .
H16A H 0.5348 0.0795 0.9760 0.160 Uiso 1 1 calc R . .
H16B H 0.6558 -0.0034 1.0189 0.160 Uiso 1 1 calc R . .
H16C H 0.4616 -0.0224 1.0190 0.160 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 C13 1.136(3) . ?
O1 C1 1.369(3) . ?
O1 C5 1.391(3) . ?
O2 C1 1.187(3) . ?
O3 C14 1.199(3) . ?
O4 C14 1.336(3) . ?
O4 C15 1.465(3) . ?
C1 C2 1.480(3) . ?
C2 C3 1.546(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C13 1.483(3) . ?
C3 C4 1.528(3) . ?
C3 C7 1.544(3) . ?
C4 C5 1.332(3) . ?
C4 C14 1.482(3) . ?
C5 C6 1.492(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.382(3) . ?
C7 C12 1.389(3) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C15 C16 1.475(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C1 O1 C5 121.23(17) . . ?
C14 O4 C15 117.0(2) . . ?
O2 C1 O1 117.3(2) . . ?
O2 C1 C2 126.6(2) . . ?
O1 C1 C2 116.0(2) . . ?
C1 C2 C3 113.46(19) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C13 C3 C4 108.87(18) . . ?
C13 C3 C7 111.04(19) . . ?
C4 C3 C7 112.62(18) . . ?
C13 C3 C2 108.40(17) . . ?
C4 C3 C2 108.18(17) . . ?
C7 C3 C2 107.61(17) . . ?
C5 C4 C14 120.5(2) . . ?
C5 C4 C3 120.7(2) . . ?
C14 C4 C3 118.75(18) . . ?
C4 C5 O1 122.8(2) . . ?
C4 C5 C6 128.8(2) . . ?
O1 C5 C6 108.3(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 119.6(2) . . ?
C8 C7 C3 118.3(2) . . ?
C12 C7 C3 122.0(2) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 119.3(3) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N1 C13 C3 177.2(3) . . ?
O3 C14 O4 123.8(2) . . ?
O3 C14 C4 126.2(2) . . ?
O4 C14 C4 110.0(2) . . ?
O4 C15 C16 111.8(3) . . ?
O4 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
O4 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C5 O1 C1 O2 168.6(2) . . . . ?
C5 O1 C1 C2 -13.8(3) . . . . ?
O2 C1 C2 C3 -139.7(3) . . . . ?
O1 C1 C2 C3 43.1(3) . . . . ?
C1 C2 C3 C13 72.1(2) . . . . ?
C1 C2 C3 C4 -45.8(2) . . . . ?
C1 C2 C3 C7 -167.71(19) . . . . ?
C13 C3 C4 C5 -94.2(2) . . . . ?
C7 C3 C4 C5 142.2(2) . . . . ?
C2 C3 C4 C5 23.4(3) . . . . ?
C13 C3 C4 C14 82.6(2) . . . . ?
C7 C3 C4 C14 -41.0(3) . . . . ?
C2 C3 C4 C14 -159.77(18) . . . . ?
C14 C4 C5 O1 -172.0(2) . . . . ?
C3 C4 C5 O1 4.8(3) . . . . ?
C14 C4 C5 C6 5.4(4) . . . . ?
C3 C4 C5 C6 -177.9(2) . . . . ?
C1 O1 C5 C4 -11.3(4) . . . . ?
C1 O1 C5 C6 170.8(2) . . . . ?
C13 C3 C7 C8 -169.1(2) . . . . ?
C4 C3 C7 C8 -46.7(3) . . . . ?
C2 C3 C7 C8 72.4(3) . . . . ?
C13 C3 C7 C12 14.3(3) . . . . ?
C4 C3 C7 C12 136.7(2) . . . . ?
C2 C3 C7 C12 -104.2(3) . . . . ?
C12 C7 C8 C9 -0.2(4) . . . . ?
C3 C7 C8 C9 -176.8(3) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C11 -0.7(6) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C8 C7 C12 C11 0.1(4) . . . . ?
C3 C7 C12 C11 176.6(3) . . . . ?
C10 C11 C12 C7 -0.3(5) . . . . ?
C4 C3 C13 N1 94(6) . . . . ?
C7 C3 C13 N1 -142(6) . . . . ?
C2 C3 C13 N1 -24(6) . . . . ?
C15 O4 C14 O3 -7.7(4) . . . . ?
C15 O4 C14 C4 172.5(2) . . . . ?
C5 C4 C14 O3 -31.6(4) . . . . ?
C3 C4 C14 O3 151.5(3) . . . . ?
C5 C4 C14 O4 148.1(2) . . . . ?
C3 C4 C14 O4 -28.7(3) . . . . ?
C14 O4 C15 C16 -81.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.032
_chemical_properties_physical    ', Moisture-sensitive'
