# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_x
_database_code_depnum_ccdc_archive 'CCDC 1577355'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N3 O4'
_chemical_formula_weight         403.43

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           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   12.911(3)
_cell_length_b                   18.214(4)
_cell_length_c                   8.5540(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.90(3)
_cell_angle_gamma                90.00
_cell_volume                     2010.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_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    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_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  ?
_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            3957
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.37
_reflns_number_total             3694
_reflns_number_gt                1857
_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)+(0.1000P)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         3694
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2222
_refine_ls_R_factor_gt           0.1264
_refine_ls_wR_factor_ref         0.3178
_refine_ls_wR_factor_gt          0.2715
_refine_ls_goodness_of_fit_ref   1.538
_refine_ls_restrained_S_all      1.538
_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 0.5897(3) -0.0620(2) 0.6372(5) 0.0519(12) Uani 1 1 d . . .
N1 N 0.6962(3) -0.0981(3) 0.8318(5) 0.0373(12) Uani 1 1 d . . .
C1 C 0.7262(4) -0.0727(3) 0.9839(6) 0.0335(13) Uani 1 1 d . . .
N2 N 0.5554(3) 0.0669(3) 0.8430(5) 0.0370(12) Uani 1 1 d . . .
O2 O 0.4405(4) 0.2208(3) 0.9621(6) 0.0667(14) Uani 1 1 d . . .
O4 O 0.8136(3) 0.1445(3) 0.8526(6) 0.0675(15) Uani 1 1 d . . .
C2 C 0.7977(5) -0.0993(4) 1.0921(7) 0.0465(16) Uani 1 1 d . . .
H2A H 0.8334 -0.1426 1.0733 0.056 Uiso 1 1 calc R . .
N3 N 0.5381(3) 0.1179(3) 0.9501(6) 0.0399(12) Uani 1 1 d U . .
O3 O 0.8076(4) 0.0599(3) 0.6642(6) 0.0719(15) Uani 1 1 d . . .
C3 C 0.8158(5) -0.0608(4) 1.2286(8) 0.0541(18) Uani 1 1 d . . .
H3B H 0.8665 -0.0775 1.2998 0.065 Uiso 1 1 calc R . .
C4 C 0.7610(4) 0.0017(4) 1.2629(6) 0.0470(17) Uani 1 1 d . . .
H4A H 0.7722 0.0250 1.3587 0.056 Uiso 1 1 calc R . .
C5 C 0.6918(5) 0.0289(4) 1.1589(8) 0.0540(18) Uani 1 1 d . . .
H5A H 0.6554 0.0712 1.1833 0.065 Uiso 1 1 calc R . .
C6 C 0.6729(4) -0.0046(3) 1.0153(6) 0.0350(14) Uani 1 1 d . . .
C7 C 0.6130(4) 0.0096(3) 0.8727(7) 0.0363(14) Uani 1 1 d . . .
C8 C 0.6300(4) -0.0540(3) 0.7636(7) 0.0324(13) Uani 1 1 d . . .
C9 C 0.7296(5) -0.1688(3) 0.7803(7) 0.0473(16) Uani 1 1 d . . .
H9A H 0.6846 -0.1847 0.6938 0.057 Uiso 1 1 calc R . .
H9B H 0.7227 -0.2038 0.8648 0.057 Uiso 1 1 calc R . .
C10 C 0.8408(5) -0.1694(4) 0.7285(8) 0.0474(17) Uani 1 1 d . . .
C11 C 0.9044(5) -0.2277(4) 0.7874(10) 0.074(2) Uani 1 1 d . . .
H11A H 0.8794 -0.2624 0.8565 0.089 Uiso 1 1 calc R . .
C12 C 1.0080(6) -0.2303(6) 0.7356(12) 0.087(3) Uani 1 1 d . . .
H12A H 1.0484 -0.2715 0.7575 0.105 Uiso 1 1 calc R . .
C13 C 1.0472(6) -0.1756(6) 0.6577(12) 0.091(3) Uani 1 1 d . . .
H13A H 1.1175 -0.1759 0.6372 0.109 Uiso 1 1 calc R . .
C14 C 0.9866(6) -0.1173(5) 0.6049(9) 0.076(2) Uani 1 1 d . . .
H14A H 1.0137 -0.0810 0.5417 0.091 Uiso 1 1 calc R . .
C15 C 0.8839(6) -0.1149(5) 0.6497(9) 0.066(2) Uani 1 1 d . . .
H15A H 0.8441 -0.0738 0.6238 0.079 Uiso 1 1 calc R . .
C16 C 0.5141(4) 0.0878(3) 0.6857(6) 0.0358(14) Uani 1 1 d . . .
H16A H 0.4750 0.0465 0.6402 0.043 Uiso 1 1 calc R . .
C17 C 0.4421(4) 0.1482(4) 0.7179(7) 0.0440(16) Uani 1 1 d . . .
H17A H 0.3705 0.1324 0.7075 0.053 Uiso 1 1 calc R . .
H17B H 0.4529 0.1898 0.6496 0.053 Uiso 1 1 calc R . .
C18 C 0.4728(4) 0.1662(3) 0.8878(7) 0.0420(15) Uani 1 1 d U . .
C19 C 0.6031(4) 0.1096(4) 0.5734(7) 0.0518(18) Uani 1 1 d . . .
H19A H 0.6359 0.0655 0.5352 0.062 Uiso 1 1 calc R . .
H19B H 0.5737 0.1360 0.4840 0.062 Uiso 1 1 calc R . .
C20 C 0.6835(5) 0.1571(4) 0.6566(8) 0.0506(17) Uani 1 1 d . . .
C21 C 0.6810(6) 0.2279(5) 0.6637(12) 0.099(3) Uani 1 1 d . . .
H21A H 0.7346 0.2533 0.7146 0.118 Uiso 1 1 calc R . .
H21B H 0.6254 0.2534 0.6180 0.118 Uiso 1 1 calc R . .
C22 C 0.7735(5) 0.1159(4) 0.7306(9) 0.0523(18) Uani 1 1 d . . .
C23 C 0.9027(6) 0.1057(5) 0.9234(10) 0.089(3) Uani 1 1 d . . .
H23A H 0.9271 0.1316 1.0153 0.134 Uiso 1 1 calc R . .
H23B H 0.9571 0.1032 0.8497 0.134 Uiso 1 1 calc R . .
H23C H 0.8824 0.0569 0.9515 0.134 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
O1 C8 1.194(6) . ?
N1 C8 1.297(7) . ?
N1 C1 1.422(7) . ?
N1 C9 1.432(7) . ?
C1 C2 1.374(8) . ?
C1 C6 1.448(8) . ?
N2 C7 1.302(7) . ?
N2 N3 1.328(6) . ?
N2 C16 1.480(7) . ?
O2 C18 1.259(7) . ?
O4 C22 1.262(8) . ?
O4 C23 1.465(8) . ?
C2 C3 1.375(9) . ?
C2 H2A 0.9300 . ?
N3 C18 1.319(7) . ?
O3 C22 1.254(8) . ?
C3 C4 1.377(9) . ?
C3 H3B 0.9300 . ?
C4 C5 1.336(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.385(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.446(8) . ?
C7 C8 1.508(8) . ?
C9 C10 1.517(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.333(9) . ?
C10 C11 1.424(9) . ?
C11 C12 1.424(11) . ?
C11 H11A 0.9300 . ?
C12 C13 1.310(12) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(11) . ?
C13 H13A 0.9300 . ?
C14 C15 1.393(9) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.472(8) . ?
C16 C19 1.573(8) . ?
C16 H16A 0.9800 . ?
C17 C18 1.529(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C20 1.511(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.292(10) . ?
C20 C22 1.504(9) . ?
C21 H21A 0.9300 . ?
C21 H21B 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C8 N1 C1 111.4(5) . . ?
C8 N1 C9 128.2(5) . . ?
C1 N1 C9 119.9(5) . . ?
C2 C1 N1 131.1(5) . . ?
C2 C1 C6 119.3(5) . . ?
N1 C1 C6 109.4(5) . . ?
C7 N2 N3 122.2(5) . . ?
C7 N2 C16 124.8(5) . . ?
N3 N2 C16 112.5(5) . . ?
C22 O4 C23 115.9(7) . . ?
C1 C2 C3 119.0(6) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C18 N3 N2 107.9(5) . . ?
C2 C3 C4 121.9(6) . . ?
C2 C3 H3B 119.1 . . ?
C4 C3 H3B 119.1 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 121.4(6) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C7 138.0(6) . . ?
C5 C6 C1 118.1(5) . . ?
C7 C6 C1 103.9(5) . . ?
N2 C7 C6 126.5(5) . . ?
N2 C7 C8 126.1(5) . . ?
C6 C7 C8 107.5(5) . . ?
O1 C8 N1 126.3(5) . . ?
O1 C8 C7 125.9(5) . . ?
N1 C8 C7 107.7(5) . . ?
N1 C9 C10 113.2(5) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 119.3(6) . . ?
C15 C10 C9 123.9(6) . . ?
C11 C10 C9 116.2(6) . . ?
C12 C11 C10 116.8(8) . . ?
C12 C11 H11A 121.6 . . ?
C10 C11 H11A 121.6 . . ?
C13 C12 C11 121.1(8) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C14 121.7(8) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C13 C14 C15 117.8(8) . . ?
C13 C14 H14A 121.1 . . ?
C15 C14 H14A 121.1 . . ?
C10 C15 C14 122.2(7) . . ?
C10 C15 H15A 118.9 . . ?
C14 C15 H15A 118.9 . . ?
C17 C16 N2 103.5(4) . . ?
C17 C16 C19 113.8(5) . . ?
N2 C16 C19 111.8(4) . . ?
C17 C16 H16A 109.2 . . ?
N2 C16 H16A 109.2 . . ?
C19 C16 H16A 109.2 . . ?
C16 C17 C18 101.1(5) . . ?
C16 C17 H17A 111.5 . . ?
C18 C17 H17A 111.5 . . ?
C16 C17 H17B 111.5 . . ?
C18 C17 H17B 111.5 . . ?
H17A C17 H17B 109.4 . . ?
O2 C18 N3 122.8(6) . . ?
O2 C18 C17 124.7(5) . . ?
N3 C18 C17 112.5(5) . . ?
C20 C19 C16 111.2(5) . . ?
C20 C19 H19A 109.4 . . ?
C16 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C16 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C22 119.9(7) . . ?
C21 C20 C19 125.1(7) . . ?
C22 C20 C19 115.0(6) . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
O3 C22 O4 124.7(7) . . ?
O3 C22 C20 119.5(6) . . ?
O4 C22 C20 115.6(7) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 N1 C1 C2 -175.8(6) . . . . ?
C9 N1 C1 C2 11.3(9) . . . . ?
C8 N1 C1 C6 -0.1(6) . . . . ?
C9 N1 C1 C6 -173.0(5) . . . . ?
N1 C1 C2 C3 176.1(6) . . . . ?
C6 C1 C2 C3 0.8(9) . . . . ?
C7 N2 N3 C18 -176.5(5) . . . . ?
C16 N2 N3 C18 11.0(6) . . . . ?
C1 C2 C3 C4 3.0(10) . . . . ?
C2 C3 C4 C5 -3.6(10) . . . . ?
C3 C4 C5 C6 0.2(10) . . . . ?
C4 C5 C6 C7 -174.4(6) . . . . ?
C4 C5 C6 C1 3.5(9) . . . . ?
C2 C1 C6 C5 -4.0(8) . . . . ?
N1 C1 C6 C5 179.8(5) . . . . ?
C2 C1 C6 C7 174.5(5) . . . . ?
N1 C1 C6 C7 -1.7(6) . . . . ?
N3 N2 C7 C6 -5.9(8) . . . . ?
C16 N2 C7 C6 165.7(5) . . . . ?
N3 N2 C7 C8 174.6(5) . . . . ?
C16 N2 C7 C8 -13.7(8) . . . . ?
C5 C6 C7 N2 1.2(11) . . . . ?
C1 C6 C7 N2 -176.9(5) . . . . ?
C5 C6 C7 C8 -179.3(7) . . . . ?
C1 C6 C7 C8 2.7(5) . . . . ?
C1 N1 C8 O1 -178.3(5) . . . . ?
C9 N1 C8 O1 -6.1(10) . . . . ?
C1 N1 C8 C7 1.8(6) . . . . ?
C9 N1 C8 C7 174.0(5) . . . . ?
N2 C7 C8 O1 -3.2(9) . . . . ?
C6 C7 C8 O1 177.2(5) . . . . ?
N2 C7 C8 N1 176.7(5) . . . . ?
C6 C7 C8 N1 -2.9(6) . . . . ?
C8 N1 C9 C10 109.9(7) . . . . ?
C1 N1 C9 C10 -78.5(6) . . . . ?
N1 C9 C10 C15 -38.2(9) . . . . ?
N1 C9 C10 C11 133.1(6) . . . . ?
C15 C10 C11 C12 -10.3(11) . . . . ?
C9 C10 C11 C12 178.0(7) . . . . ?
C10 C11 C12 C13 10.3(13) . . . . ?
C11 C12 C13 C14 -8.4(15) . . . . ?
C12 C13 C14 C15 5.9(14) . . . . ?
C11 C10 C15 C14 8.6(11) . . . . ?
C9 C10 C15 C14 179.6(7) . . . . ?
C13 C14 C15 C10 -6.1(12) . . . . ?
C7 N2 C16 C17 171.4(5) . . . . ?
N3 N2 C16 C17 -16.3(6) . . . . ?
C7 N2 C16 C19 -65.7(7) . . . . ?
N3 N2 C16 C19 106.6(5) . . . . ?
N2 C16 C17 C18 13.6(5) . . . . ?
C19 C16 C17 C18 -108.0(5) . . . . ?
N2 N3 C18 O2 179.1(5) . . . . ?
N2 N3 C18 C17 -1.1(6) . . . . ?
C16 C17 C18 O2 171.2(6) . . . . ?
C16 C17 C18 N3 -8.7(6) . . . . ?
C17 C16 C19 C20 74.1(7) . . . . ?
N2 C16 C19 C20 -42.7(7) . . . . ?
C16 C19 C20 C21 -89.6(9) . . . . ?
C16 C19 C20 C22 92.3(7) . . . . ?
C23 O4 C22 O3 -3.6(9) . . . . ?
C23 O4 C22 C20 -178.6(5) . . . . ?
C21 C20 C22 O3 -142.4(8) . . . . ?
C19 C20 C22 O3 35.8(9) . . . . ?
C21 C20 C22 O4 32.9(10) . . . . ?
C19 C20 C22 O4 -148.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.105
