# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1522097'
_audit_update_record             
;
2016-12-10 deposited with the CCDC.
2017-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O4'
_chemical_formula_weight         348.35

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1889(3)
_cell_length_b                   10.3419(5)
_cell_length_c                   10.9166(4)
_cell_angle_alpha                105.058(4)
_cell_angle_beta                 98.466(3)
_cell_angle_gamma                99.563(3)
_cell_volume                     862.59(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3075
_cell_measurement_theta_min      3.5320
_cell_measurement_theta_max      31.4070

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_T_min  0.77304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            10763
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.947
_diffrn_reflns_theta_max         32.231
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5548
_reflns_number_gt                3537
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²+0.2823P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5548
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0808(2) 0.13933(15) 0.54677(14) 0.0621(4) Uani 1 1 d . . . . .
O2 O -0.09407(17) 0.17437(13) 0.35230(12) 0.0489(3) Uani 1 1 d . . . . .
O3 O -0.4200(2) 0.3503(4) 0.8023(2) 0.1512(14) Uani 1 1 d . . . . .
O4 O -0.3824(2) 0.2876(2) 0.97225(17) 0.0853(6) Uani 1 1 d . . . . .
N1 N 0.27395(18) 0.51658(15) 0.47313(14) 0.0407(3) Uani 1 1 d . . . . .
N2 N -0.3306(2) 0.3210(2) 0.88384(18) 0.0667(6) Uani 1 1 d . . . . .
C1 C 0.3341(2) 0.57979(17) 0.59962(16) 0.0350(3) Uani 1 1 d . . . . .
C2 C 0.2695(2) 0.53046(18) 0.69452(16) 0.0381(4) Uani 1 1 d . . . . .
H2 H 0.3124 0.5771 0.7815 0.046 Uiso 1 1 calc R U . . .
C3 C 0.14224(19) 0.41283(17) 0.66104(16) 0.0348(3) Uani 1 1 d . . . . .
C4 C 0.0849(2) 0.34427(17) 0.52862(16) 0.0355(3) Uani 1 1 d . . . . .
C5 C 0.1551(2) 0.40186(18) 0.44075(17) 0.0399(4) Uani 1 1 d . . . . .
H5 H 0.1159 0.3568 0.3530 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4686(2) 0.70618(18) 0.63307(16) 0.0366(3) Uani 1 1 d . . . . .
C7 C 0.5108(2) 0.7633(2) 0.53658(19) 0.0483(4) Uani 1 1 d . . . . .
H7 H 0.4553 0.7209 0.4512 0.058 Uiso 1 1 calc R U . . .
C8 C 0.6338(3) 0.8820(2) 0.5655(2) 0.0552(5) Uani 1 1 d . . . . .
H8 H 0.6592 0.9190 0.4998 0.066 Uiso 1 1 calc R U . . .
C9 C 0.7189(3) 0.9454(2) 0.6911(2) 0.0577(5) Uani 1 1 d . . . . .
H9 H 0.8017 1.0251 0.7108 0.069 Uiso 1 1 calc R U . . .
C10 C 0.6799(3) 0.8896(3) 0.7870(2) 0.0664(7) Uani 1 1 d . . . . .
H10 H 0.7373 0.9318 0.8719 0.080 Uiso 1 1 calc R U . . .
C11 C 0.5563(3) 0.7713(2) 0.75899(19) 0.0543(5) Uani 1 1 d . . . . .
H11 H 0.5317 0.7351 0.8254 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0738(2) 0.37130(17) 0.76781(16) 0.0359(3) Uani 1 1 d . . . . .
C13 C 0.1815(2) 0.3502(2) 0.86757(19) 0.0474(4) Uani 1 1 d . . . . .
H13 H 0.2958 0.3579 0.8653 0.057 Uiso 1 1 calc R U . . .
C14 C 0.1221(3) 0.3177(2) 0.9709(2) 0.0541(5) Uani 1 1 d . . . . .
H14 H 0.1966 0.3031 1.0364 0.065 Uiso 1 1 calc R U . . .
C15 C -0.0465(3) 0.3068(2) 0.97717(18) 0.0488(5) Uani 1 1 d . . . . .
H15 H -0.0877 0.2848 1.0458 0.059 Uiso 1 1 calc R U . . .
C16 C -0.1511(2) 0.32969(19) 0.87796(17) 0.0426(4) Uani 1 1 d . . . . .
C17 C -0.0961(2) 0.36190(19) 0.77347(16) 0.0399(4) Uani 1 1 d . . . . .
H17 H -0.1711 0.3769 0.7085 0.048 Uiso 1 1 calc R U . . .
C18 C -0.0387(2) 0.21015(18) 0.48054(17) 0.0398(4) Uani 1 1 d . . . . .
C19 C -0.2064(3) 0.0407(2) 0.29442(19) 0.0506(5) Uani 1 1 d . . . . .
H19A H -0.3119 0.0387 0.3250 0.061 Uiso 1 1 calc R U . . .
H19B H -0.1544 -0.0300 0.3168 0.061 Uiso 1 1 calc R U . . .
C20 C -0.2376(3) 0.0178(3) 0.1508(2) 0.0668(6) Uani 1 1 d . . . . .
H20A H -0.2885 0.0887 0.1302 0.100 Uiso 1 1 calc R U . . .
H20B H -0.3120 -0.0697 0.1083 0.100 Uiso 1 1 calc R U . . .
H20C H -0.1322 0.0198 0.1220 0.100 Uiso 1 1 calc R U . . .


_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 C18 1.201(2) . ?
O2 C18 1.338(2) . ?
O2 C19 1.452(2) . ?
O3 N2 1.201(3) . ?
O4 N2 1.214(2) . ?
N1 C5 1.333(2) . ?
N1 C1 1.342(2) . ?
N2 C16 1.470(2) . ?
C1 C2 1.400(2) . ?
C1 C6 1.487(2) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(2) . ?
C3 C12 1.493(2) . ?
C4 C5 1.397(2) . ?
C4 C18 1.491(2) . ?
C5 H5 0.9300 . ?
C6 C11 1.388(3) . ?
C6 C7 1.393(2) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.385(2) . ?
C12 C17 1.390(2) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(2) . ?
C17 H17 0.9300 . ?
C19 C20 1.499(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C18 O2 C19 116.18(14) . . ?
C5 N1 C1 117.68(14) . . ?
O3 N2 O4 122.41(19) . . ?
O3 N2 C16 118.51(17) . . ?
O4 N2 C16 119.06(19) . . ?
N1 C1 C2 121.28(15) . . ?
N1 C1 C6 116.60(14) . . ?
C2 C1 C6 122.10(15) . . ?
C3 C2 C1 121.15(16) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 117.17(14) . . ?
C2 C3 C12 117.81(14) . . ?
C4 C3 C12 125.00(14) . . ?
C5 C4 C3 117.72(15) . . ?
C5 C4 C18 119.79(15) . . ?
C3 C4 C18 122.39(14) . . ?
N1 C5 C4 124.92(16) . . ?
N1 C5 H5 117.5 . . ?
C4 C5 H5 117.5 . . ?
C11 C6 C7 117.59(16) . . ?
C11 C6 C1 122.29(15) . . ?
C7 C6 C1 120.12(16) . . ?
C8 C7 C6 121.20(18) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.31(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.15(19) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 120.80(17) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C13 C12 C17 118.88(15) . . ?
C13 C12 C3 120.10(15) . . ?
C17 C12 C3 120.89(15) . . ?
C12 C13 C14 121.15(17) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.60(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 117.39(16) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C17 123.49(16) . . ?
C15 C16 N2 118.30(16) . . ?
C17 C16 N2 118.20(16) . . ?
C16 C17 C12 118.48(16) . . ?
C16 C17 H17 120.8 . . ?
C12 C17 H17 120.8 . . ?
O1 C18 O2 123.22(17) . . ?
O1 C18 C4 124.90(17) . . ?
O2 C18 C4 111.83(14) . . ?
O2 C19 C20 106.53(16) . . ?
O2 C19 H19A 110.4 . . ?
C20 C19 H19A 110.4 . . ?
O2 C19 H19B 110.4 . . ?
C20 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 N1 C1 C2 -2.6(2) . . . . ?
C5 N1 C1 C6 179.01(15) . . . . ?
N1 C1 C2 C3 1.0(3) . . . . ?
C6 C1 C2 C3 179.26(15) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C1 C2 C3 C12 -176.73(15) . . . . ?
C2 C3 C4 C5 -2.4(2) . . . . ?
C12 C3 C4 C5 175.83(16) . . . . ?
C2 C3 C4 C18 173.99(15) . . . . ?
C12 C3 C4 C18 -7.8(3) . . . . ?
C1 N1 C5 C4 1.8(3) . . . . ?
C3 C4 C5 N1 0.7(3) . . . . ?
C18 C4 C5 N1 -175.70(16) . . . . ?
N1 C1 C6 C11 -171.62(18) . . . . ?
C2 C1 C6 C11 10.0(3) . . . . ?
N1 C1 C6 C7 8.3(2) . . . . ?
C2 C1 C6 C7 -170.11(17) . . . . ?
C11 C6 C7 C8 -1.1(3) . . . . ?
C1 C6 C7 C8 179.06(18) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C6 0.0(4) . . . . ?
C7 C6 C11 C10 0.7(3) . . . . ?
C1 C6 C11 C10 -179.5(2) . . . . ?
C2 C3 C12 C13 -56.0(2) . . . . ?
C4 C3 C12 C13 125.81(19) . . . . ?
C2 C3 C12 C17 119.78(18) . . . . ?
C4 C3 C12 C17 -58.4(2) . . . . ?
C17 C12 C13 C14 1.1(3) . . . . ?
C3 C12 C13 C14 177.01(19) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C14 C15 C16 N2 -179.0(2) . . . . ?
O3 N2 C16 C15 174.8(3) . . . . ?
O4 N2 C16 C15 -3.5(3) . . . . ?
O3 N2 C16 C17 -4.6(4) . . . . ?
O4 N2 C16 C17 177.2(2) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
N2 C16 C17 C12 179.54(18) . . . . ?
C13 C12 C17 C16 -1.0(3) . . . . ?
C3 C12 C17 C16 -176.80(16) . . . . ?
C19 O2 C18 O1 -1.9(3) . . . . ?
C19 O2 C18 C4 175.94(15) . . . . ?
C5 C4 C18 O1 164.65(19) . . . . ?
C3 C4 C18 O1 -11.6(3) . . . . ?
C5 C4 C18 O2 -13.1(2) . . . . ?
C3 C4 C18 O2 170.61(15) . . . . ?
C18 O2 C19 C20 -174.62(17) . . . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044



