# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 1487704'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         323.34

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1250(16)
_cell_length_b                   9.3280(19)
_cell_length_c                   11.408(2)
_cell_angle_alpha                90.91(3)
_cell_angle_beta                 96.19(3)
_cell_angle_gamma                107.69(3)
_cell_volume                     817.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3234
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0973
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.37
_reflns_number_total             3007
_reflns_number_gt                1337
_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)+(0.0430P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3007
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
N N 0.7101(4) 0.5661(3) 0.6651(3) 0.0508(8) Uani 1 1 d . . .
O1 O 1.0037(4) 0.6857(3) 0.7012(3) 0.0900(11) Uani 1 1 d . . .
C1 C 0.8836(5) 0.5725(5) 0.6703(4) 0.0592(11) Uani 1 1 d . . .
O2 O 0.4444(3) 0.3880(3) 0.6031(2) 0.0697(8) Uani 1 1 d . . .
C2 C 0.8852(5) 0.4215(4) 0.6342(3) 0.0539(10) Uani 1 1 d . . .
O3 O 0.4539(4) 0.5570(3) 0.8629(2) 0.0732(9) Uani 1 1 d . . .
C3 C 1.0256(6) 0.3680(6) 0.6272(4) 0.0761(13) Uani 1 1 d . . .
H3A H 1.1397 0.4278 0.6493 0.091 Uiso 1 1 calc R . .
O4 O 0.6927(3) 0.6395(3) 0.9914(3) 0.0733(9) Uani 1 1 d . . .
H4B H 0.6354 0.5736 1.0305 0.110 Uiso 1 1 calc R . .
C4 C 0.9848(8) 0.2188(7) 0.5849(4) 0.0918(17) Uani 1 1 d . . .
H4A H 1.0745 0.1783 0.5760 0.110 Uiso 1 1 calc R . .
C5 C 0.8175(8) 0.1311(5) 0.5564(4) 0.0925(17) Uani 1 1 d . . .
H5A H 0.7956 0.0311 0.5309 0.111 Uiso 1 1 calc R . .
C6 C 0.6766(6) 0.1868(5) 0.5643(4) 0.0757(13) Uani 1 1 d . . .
H6A H 0.5620 0.1274 0.5434 0.091 Uiso 1 1 calc R . .
C7 C 0.7177(5) 0.3323(4) 0.6043(3) 0.0540(10) Uani 1 1 d . . .
C8 C 0.6007(5) 0.4236(4) 0.6218(3) 0.0524(10) Uani 1 1 d . . .
C9 C 0.6502(5) 0.6957(4) 0.6834(3) 0.0621(11) Uani 1 1 d . . .
H9A H 0.5253 0.6665 0.6619 0.075 Uiso 1 1 calc R . .
H9B H 0.7039 0.7737 0.6320 0.075 Uiso 1 1 calc R . .
C10 C 0.6929(5) 0.7588(4) 0.8103(3) 0.0527(10) Uani 1 1 d . . .
H10A H 0.8189 0.7840 0.8312 0.063 Uiso 1 1 calc R . .
C11 C 0.6055(5) 0.6416(4) 0.8927(4) 0.0517(10) Uani 1 1 d . . .
C12 C 0.6430(5) 0.9010(4) 0.8288(3) 0.0495(10) Uani 1 1 d . . .
C13 C 0.4744(5) 0.9050(4) 0.7992(3) 0.0538(10) Uani 1 1 d . . .
H13A H 0.3895 0.8188 0.7657 0.065 Uiso 1 1 calc R . .
C14 C 0.4302(5) 1.0341(4) 0.8185(3) 0.0523(10) Uani 1 1 d . . .
C15 C 0.5605(5) 1.1602(4) 0.8698(3) 0.0546(11) Uani 1 1 d . . .
H15A H 0.5317 1.2474 0.8847 0.065 Uiso 1 1 calc R . .
C16 C 0.7301(5) 1.1622(4) 0.8995(3) 0.0556(10) Uani 1 1 d . . .
C17 C 0.7682(5) 1.0308(4) 0.8781(3) 0.0561(10) Uani 1 1 d . . .
H17A H 0.8817 1.0290 0.8974 0.067 Uiso 1 1 calc R . .
C18 C 0.2468(5) 1.0396(4) 0.7905(4) 0.0809(14) Uani 1 1 d . . .
H18A H 0.1737 0.9439 0.7558 0.121 Uiso 1 1 calc R . .
H18B H 0.2454 1.1167 0.7360 0.121 Uiso 1 1 calc R . .
H18C H 0.2044 1.0617 0.8618 0.121 Uiso 1 1 calc R . .
C19 C 0.8669(6) 1.3015(4) 0.9563(4) 0.0898(16) Uani 1 1 d . . .
H19A H 0.8163 1.3814 0.9633 0.135 Uiso 1 1 calc R . .
H19B H 0.9605 1.3319 0.9083 0.135 Uiso 1 1 calc R . .
H19C H 0.9108 1.2798 1.0332 0.135 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
N C1 1.387(4) . ?
N C8 1.402(4) . ?
N C9 1.454(4) . ?
O1 C1 1.216(4) . ?
C1 C2 1.465(5) . ?
O2 C8 1.205(4) . ?
C2 C7 1.365(5) . ?
C2 C3 1.386(5) . ?
O3 C11 1.251(4) . ?
C3 C4 1.394(6) . ?
C3 H3A 0.9300 . ?
O4 C11 1.268(4) . ?
O4 H4B 0.8200 . ?
C4 C5 1.358(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.404(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.354(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.482(5) . ?
C9 C10 1.517(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.513(5) . ?
C10 C12 1.518(4) . ?
C10 H10A 0.9800 . ?
C12 C17 1.387(5) . ?
C12 C13 1.387(5) . ?
C13 C14 1.378(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.391(5) . ?
C14 C18 1.506(5) . ?
C15 C16 1.378(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.376(5) . ?
C16 C19 1.512(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 N C8 110.9(3) . . ?
C1 N C9 124.4(3) . . ?
C8 N C9 124.0(3) . . ?
O1 C1 N 123.4(4) . . ?
O1 C1 C2 130.2(4) . . ?
N C1 C2 106.5(3) . . ?
C7 C2 C3 121.9(4) . . ?
C7 C2 C1 108.8(3) . . ?
C3 C2 C1 129.3(4) . . ?
C2 C3 C4 115.7(4) . . ?
C2 C3 H3A 122.1 . . ?
C4 C3 H3A 122.1 . . ?
C11 O4 H4B 109.5 . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
C4 C5 C6 122.0(4) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
C7 C6 C5 115.9(4) . . ?
C7 C6 H6A 122.0 . . ?
C5 C6 H6A 122.0 . . ?
C6 C7 C2 122.8(4) . . ?
C6 C7 C8 129.1(4) . . ?
C2 C7 C8 108.1(3) . . ?
O2 C8 N 125.4(3) . . ?
O2 C8 C7 129.0(4) . . ?
N C8 C7 105.6(3) . . ?
N C9 C10 112.5(3) . . ?
N C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 110.5(3) . . ?
C11 C10 C12 109.6(3) . . ?
C9 C10 C12 113.1(3) . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10A 107.8 . . ?
C12 C10 H10A 107.8 . . ?
O3 C11 O4 124.1(4) . . ?
O3 C11 C10 119.8(4) . . ?
O4 C11 C10 116.1(4) . . ?
C17 C12 C13 118.5(3) . . ?
C17 C12 C10 119.5(3) . . ?
C13 C12 C10 121.9(3) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 C18 122.2(4) . . ?
C15 C14 C18 120.1(3) . . ?
C16 C15 C14 123.2(3) . . ?
C16 C15 H15A 118.4 . . ?
C14 C15 H15A 118.4 . . ?
C17 C16 C15 117.1(4) . . ?
C17 C16 C19 121.6(4) . . ?
C15 C16 C19 121.3(3) . . ?
C16 C17 C12 122.2(4) . . ?
C16 C17 H17A 118.9 . . ?
C12 C17 H17A 118.9 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C8 N C1 O1 177.5(4) . . . . ?
C9 N C1 O1 6.8(6) . . . . ?
C8 N C1 C2 -3.3(4) . . . . ?
C9 N C1 C2 -174.0(3) . . . . ?
O1 C1 C2 C7 -178.4(5) . . . . ?
N C1 C2 C7 2.4(4) . . . . ?
O1 C1 C2 C3 0.8(8) . . . . ?
N C1 C2 C3 -178.3(4) . . . . ?
C7 C2 C3 C4 1.6(6) . . . . ?
C1 C2 C3 C4 -177.6(4) . . . . ?
C2 C3 C4 C5 -2.1(7) . . . . ?
C3 C4 C5 C6 2.0(8) . . . . ?
C4 C5 C6 C7 -1.3(7) . . . . ?
C5 C6 C7 C2 0.8(6) . . . . ?
C5 C6 C7 C8 179.5(4) . . . . ?
C3 C2 C7 C6 -1.0(7) . . . . ?
C1 C2 C7 C6 178.3(4) . . . . ?
C3 C2 C7 C8 180.0(4) . . . . ?
C1 C2 C7 C8 -0.7(4) . . . . ?
C1 N C8 O2 -176.6(4) . . . . ?
C9 N C8 O2 -5.9(6) . . . . ?
C1 N C8 C7 2.9(4) . . . . ?
C9 N C8 C7 173.6(3) . . . . ?
C6 C7 C8 O2 -0.8(7) . . . . ?
C2 C7 C8 O2 178.2(4) . . . . ?
C6 C7 C8 N 179.8(4) . . . . ?
C2 C7 C8 N -1.3(4) . . . . ?
C1 N C9 C10 -68.7(5) . . . . ?
C8 N C9 C10 121.8(4) . . . . ?
N C9 C10 C11 -60.9(4) . . . . ?
N C9 C10 C12 175.8(3) . . . . ?
C9 C10 C11 O3 -39.7(5) . . . . ?
C12 C10 C11 O3 85.6(4) . . . . ?
C9 C10 C11 O4 142.2(3) . . . . ?
C12 C10 C11 O4 -92.5(4) . . . . ?
C11 C10 C12 C17 111.8(4) . . . . ?
C9 C10 C12 C17 -124.4(4) . . . . ?
C11 C10 C12 C13 -67.3(4) . . . . ?
C9 C10 C12 C13 56.5(5) . . . . ?
C17 C12 C13 C14 -0.3(6) . . . . ?
C10 C12 C13 C14 178.8(3) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C12 C13 C14 C18 -178.1(4) . . . . ?
C13 C14 C15 C16 1.3(6) . . . . ?
C18 C14 C15 C16 178.9(4) . . . . ?
C14 C15 C16 C17 -1.0(6) . . . . ?
C14 C15 C16 C19 -179.3(4) . . . . ?
C15 C16 C17 C12 0.0(6) . . . . ?
C19 C16 C17 C12 178.3(4) . . . . ?
C13 C12 C17 C16 0.6(6) . . . . ?
C10 C12 C17 C16 -178.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.042
