# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1813383'
_audit_update_record             
;
2017-12-25 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N4 O4'
_chemical_formula_weight         476.48

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           ?
_symmetry_space_group_name_H-M   ?

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                   14.660(3)
_cell_length_b                   5.7506(12)
_cell_length_c                   14.623(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.41(3)
_cell_angle_gamma                90.00
_cell_volume                     1162.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9834
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      289(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20614
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2674
_reflns_number_gt                2177
_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)+(0.0534P)²+0.2017P] 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         2674
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.81262(7) 0.6921(2) 0.38449(8) 0.0646(3) Uani 1 1 d . . .
O2 O 0.68333(7) 0.48002(18) 0.37214(7) 0.0559(3) Uani 1 1 d . . .
N1 N 0.86523(9) 0.8806(3) 0.44227(10) 0.0637(4) Uani 1 1 d . . .
N2 N 0.73414(7) 0.79127(18) 0.48396(7) 0.0424(3) Uani 1 1 d . . .
C1 C 0.80863(10) 1.1130(2) 0.64871(10) 0.0515(3) Uani 1 1 d . . .
H1 H 0.7652 0.9987 0.6527 0.062 Uiso 1 1 calc R . .
C2 C 0.83785(11) 1.2824(3) 0.71956(11) 0.0609(4) Uani 1 1 d . . .
H2 H 0.8143 1.2812 0.7713 0.073 Uiso 1 1 calc R . .
C3 C 0.90165(11) 1.4528(3) 0.71372(12) 0.0643(4) Uani 1 1 d . . .
H3 H 0.9210 1.5668 0.7614 0.077 Uiso 1 1 calc R . .
C4 C 0.93671(11) 1.4542(3) 0.63740(13) 0.0660(4) Uani 1 1 d . . .
H4 H 0.9796 1.5698 0.6335 0.079 Uiso 1 1 calc R . .
C5 C 0.90868(10) 1.2851(3) 0.56650(11) 0.0554(4) Uani 1 1 d . . .
H5 H 0.9330 1.2864 0.5153 0.066 Uiso 1 1 calc R . .
C6 C 0.84391(8) 1.1129(2) 0.57166(9) 0.0429(3) Uani 1 1 d . . .
C7 C 0.56049(10) 0.2754(2) 0.41322(9) 0.0481(3) Uani 1 1 d . . .
H7 H 0.6047 0.1574 0.4400 0.058 Uiso 1 1 calc R . .
C8 C 0.46570(10) 0.2571(2) 0.40964(9) 0.0509(3) Uani 1 1 d . . .
H8 H 0.4455 0.1253 0.4344 0.061 Uiso 1 1 calc R . .
C9 C 0.40056(10) 0.4320(2) 0.36984(9) 0.0471(3) Uani 1 1 d . . .
H9 H 0.3367 0.4182 0.3678 0.056 Uiso 1 1 calc R . .
C10 C 0.43019(9) 0.6282(2) 0.33286(9) 0.0444(3) Uani 1 1 d . . .
H10 H 0.3861 0.7462 0.3059 0.053 Uiso 1 1 calc R . .
C11 C 0.52472(9) 0.6501(2) 0.33561(8) 0.0411(3) Uani 1 1 d . . .
H11 H 0.5451 0.7815 0.3108 0.049 Uiso 1 1 calc R . .
C12 C 0.58796(9) 0.4725(2) 0.37610(8) 0.0395(3) Uani 1 1 d . . .
C13 C 0.81483(8) 0.9292(2) 0.49799(9) 0.0431(3) Uani 1 1 d . . .
C14 C 0.73890(9) 0.6561(2) 0.41595(9) 0.0450(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0579(6) 0.0800(7) 0.0668(6) -0.0224(6) 0.0353(5) -0.0079(5)
O2 0.0472(5) 0.0583(6) 0.0631(6) -0.0243(5) 0.0195(4) -0.0001(4)
N1 0.0532(7) 0.0757(9) 0.0711(8) -0.0175(7) 0.0325(6) -0.0128(6)
N2 0.0359(5) 0.0454(6) 0.0464(6) -0.0060(5) 0.0144(4) 0.0004(4)
C1 0.0451(7) 0.0515(8) 0.0576(8) -0.0076(6) 0.0165(6) -0.0060(6)
C2 0.0563(8) 0.0636(9) 0.0590(9) -0.0126(7) 0.0142(7) 0.0018(7)
C3 0.0536(8) 0.0537(9) 0.0697(10) -0.0142(7) -0.0010(7) 0.0014(7)
C4 0.0483(8) 0.0523(9) 0.0841(12) -0.0006(8) 0.0041(8) -0.0118(6)
C5 0.0411(7) 0.0578(8) 0.0632(9) 0.0050(7) 0.0120(6) -0.0039(6)
C6 0.0296(5) 0.0439(7) 0.0498(7) 0.0010(5) 0.0060(5) 0.0028(5)
C7 0.0614(8) 0.0363(6) 0.0392(6) 0.0018(5) 0.0069(6) 0.0093(6)
C8 0.0678(9) 0.0395(7) 0.0450(7) 0.0060(5) 0.0181(6) -0.0057(6)
C9 0.0495(7) 0.0493(7) 0.0440(7) -0.0011(6) 0.0176(6) -0.0045(6)
C10 0.0490(7) 0.0394(6) 0.0428(6) 0.0030(5) 0.0126(5) 0.0063(5)
C11 0.0515(7) 0.0347(6) 0.0364(6) 0.0017(5) 0.0139(5) -0.0023(5)
C12 0.0431(6) 0.0405(6) 0.0331(6) -0.0096(5) 0.0100(5) 0.0009(5)
C13 0.0340(6) 0.0489(7) 0.0461(7) 0.0017(5) 0.0130(5) 0.0033(5)
C14 0.0383(6) 0.0507(7) 0.0465(7) -0.0056(6) 0.0147(5) 0.0051(5)

_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 C14 1.3241(16) . ?
O1 N1 1.4318(16) . ?
O2 C14 1.3237(16) . ?
O2 C12 1.4190(15) . ?
N1 C13 1.2991(17) . ?
N2 C14 1.2824(16) . ?
N2 C13 1.3816(16) . ?
C1 C2 1.382(2) . ?
C1 C6 1.3872(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3914(19) . ?
C5 H5 0.9300 . ?
C6 C13 1.4674(18) . ?
C7 C12 1.3736(18) . ?
C7 C8 1.377(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.3754(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.3822(18) . ?
C9 H9 0.9300 . ?
C10 C11 1.3788(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.3744(17) . ?
C11 H11 0.9300 . ?

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
C14 O1 N1 104.79(10) . . ?
C14 O2 C12 117.38(9) . . ?
C13 N1 O1 103.05(10) . . ?
C14 N2 C13 101.45(11) . . ?
C2 C1 C6 120.18(13) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.19(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.96(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.47(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.92(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.28(13) . . ?
C1 C6 C13 120.06(12) . . ?
C5 C6 C13 120.64(13) . . ?
C12 C7 C8 118.19(12) . . ?
C12 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C9 C8 C7 120.69(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.86(12) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.45(12) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 118.17(11) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C7 C12 C11 122.63(12) . . ?
C7 C12 O2 117.61(11) . . ?
C11 C12 O2 119.50(11) . . ?
N1 C13 N2 114.88(12) . . ?
N1 C13 C6 121.89(12) . . ?
N2 C13 C6 123.21(11) . . ?
N2 C14 O2 130.98(12) . . ?
N2 C14 O1 115.82(12) . . ?
O2 C14 O1 113.18(11) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
