# 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 2019

####################################################################### 
# 
# 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_sg-1_a
_database_code_depnum_ccdc_archive 'CCDC 1921903'
_audit_update_record             
;
2019-06-08 deposited with the CCDC.	2019-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 N4 O5'
_chemical_formula_weight         352.31

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   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7345(8)
_cell_length_b                   7.2239(6)
_cell_length_c                   13.9285(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.600(7)
_cell_angle_gamma                90.00
_cell_volume                     778.19(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5567
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            derk-red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8604
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2704
_reflns_number_gt                2272
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0050P)²+12.2189P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(7)
_refine_ls_number_reflns         2704
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1623
_refine_ls_R_factor_gt           0.1504
_refine_ls_wR_factor_ref         0.3589
_refine_ls_wR_factor_gt          0.3544
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.2162(15) 0.6915(15) 0.0881(6) 0.059(3) Uani 1 1 d . . .
H1 H 0.1358 0.6183 0.0816 0.089 Uiso 1 1 calc R . .
N4 N 0.6919(18) -0.2188(16) 0.1357(13) 0.071(5) Uani 1 1 d . . .
N3 N 0.6151(15) 0.1726(17) 0.4268(7) 0.046(3) Uani 1 1 d . . .
N1 N 0.3508(15) 0.5657(14) 0.2416(8) 0.046(3) Uani 1 1 d . . .
O3 O 0.6966(15) 0.0524(15) 0.4723(7) 0.065(3) Uani 1 1 d . . .
C4 C 0.1366(17) 1.0054(17) 0.2840(9) 0.040(3) Uani 1 1 d . . .
O4 O 0.7600(19) -0.3303(16) 0.1937(10) 0.093(4) Uani 1 1 d . . .
C3 C 0.1932(18) 0.8440(15) 0.2346(8) 0.036(3) Uani 1 1 d . . .
C11 C 0.2810(17) 0.6940(19) 0.2902(8) 0.042(3) Uani 1 1 d . . .
H11 H 0.2845 0.6943 0.3570 0.051 Uiso 1 1 calc R . .
N2 N 0.4289(15) 0.4327(15) 0.3019(8) 0.047(3) Uani 1 1 d . . .
H2 H 0.4283 0.4519 0.3629 0.057 Uiso 1 1 calc R . .
C15 C 0.6312(17) -0.0430(15) 0.1857(9) 0.040(3) Uani 1 1 d . . .
C5 C 0.1603(18) 1.0430(18) 0.3863(8) 0.044(3) Uani 1 1 d . . .
H5 H 0.2123 0.9542 0.4254 0.053 Uiso 1 1 calc R . .
O5 O 0.661(2) -0.2356(18) 0.0583(9) 0.099(5) Uani 1 1 d . . .
C14 C 0.5495(17) 0.0871(18) 0.1262(9) 0.045(3) Uani 1 1 d . . .
H14 H 0.5358 0.0658 0.0607 0.053 Uiso 1 1 calc R . .
C10 C 0.023(2) 1.135(2) 0.1389(10) 0.058(4) Uani 1 1 d . . .
H10 H -0.0335 1.2306 0.1063 0.069 Uiso 1 1 calc R . .
C1 C 0.078(2) 0.978(2) 0.0895(10) 0.057(4) Uani 1 1 d . . .
H1A H 0.0569 0.9669 0.0239 0.068 Uiso 1 1 calc R . .
O2 O 0.5566(19) 0.2985(17) 0.4661(7) 0.089(5) Uani 1 1 d . . .
C9 C 0.0511(17) 1.1474(19) 0.2321(11) 0.051(4) Uani 1 1 d . . .
C17 C 0.5868(17) 0.1452(18) 0.3209(9) 0.042(3) Uani 1 1 d . . .
C8 C -0.006(2) 1.3113(18) 0.2770(12) 0.059(4) Uani 1 1 d . . .
H8 H -0.0622 1.4019 0.2408 0.071 Uiso 1 1 calc R . .
C2 C 0.164(2) 0.837(2) 0.1393(9) 0.058(4) Uani 1 1 d . . .
C16 C 0.6521(16) -0.0134(18) 0.2828(9) 0.042(3) Uani 1 1 d . . .
H16 H 0.7094 -0.0994 0.3214 0.050 Uiso 1 1 calc R . .
C6 C 0.110(2) 1.198(2) 0.4234(10) 0.058(4) Uani 1 1 d . . .
H6 H 0.1376 1.2155 0.4880 0.070 Uiso 1 1 calc R . .
C13 C 0.488(2) 0.252(2) 0.1688(9) 0.052(4) Uani 1 1 d . . .
H13 H 0.4378 0.3445 0.1312 0.062 Uiso 1 1 calc R . .
C12 C 0.5054(17) 0.275(2) 0.2692(10) 0.045(3) Uani 1 1 d . . .
C7 C 0.022(2) 1.340(2) 0.3799(14) 0.076(6) Uani 1 1 d . . .
H7 H -0.0166 1.4440 0.4126 0.091 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 C2 1.338(16) . ?
O1 H1 0.8200 . ?
N4 O5 1.109(17) . ?
N4 O4 1.254(19) . ?
N4 C15 1.525(15) . ?
N3 O2 1.156(15) . ?
N3 O3 1.243(14) . ?
N3 C17 1.503(14) . ?
N1 C11 1.272(16) . ?
N1 N2 1.409(13) . ?
C4 C9 1.415(17) . ?
C4 C3 1.425(16) . ?
C4 C5 1.460(16) . ?
C3 C2 1.344(17) . ?
C3 C11 1.492(16) . ?
C11 H11 0.9300 . ?
N2 C12 1.362(18) . ?
N2 H2 0.8600 . ?
C15 C16 1.377(18) . ?
C15 C14 1.400(18) . ?
C5 C6 1.296(18) . ?
C5 H5 0.9300 . ?
C14 C13 1.416(18) . ?
C14 H14 0.9300 . ?
C10 C9 1.318(19) . ?
C10 C1 1.40(2) . ?
C10 H10 0.9300 . ?
C1 C2 1.396(19) . ?
C1 H1A 0.9300 . ?
C9 C8 1.41(2) . ?
C17 C12 1.337(18) . ?
C17 C16 1.361(17) . ?
C8 C7 1.46(2) . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C6 C7 1.37(2) . ?
C6 H6 0.9300 . ?
C13 C12 1.414(18) . ?
C13 H13 0.9300 . ?
C7 H7 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
C2 O1 H1 109.5 . . ?
O5 N4 O4 130.0(14) . . ?
O5 N4 C15 118.1(15) . . ?
O4 N4 C15 111.7(14) . . ?
O2 N3 O3 120.5(10) . . ?
O2 N3 C17 121.0(11) . . ?
O3 N3 C17 118.5(11) . . ?
C11 N1 N2 111.2(10) . . ?
C9 C4 C3 119.4(11) . . ?
C9 C4 C5 114.6(12) . . ?
C3 C4 C5 126.0(11) . . ?
C2 C3 C4 117.2(11) . . ?
C2 C3 C11 123.9(12) . . ?
C4 C3 C11 118.9(10) . . ?
N1 C11 C3 116.5(10) . . ?
N1 C11 H11 121.8 . . ?
C3 C11 H11 121.8 . . ?
C12 N2 N1 123.7(11) . . ?
C12 N2 H2 118.2 . . ?
N1 N2 H2 118.2 . . ?
C16 C15 C14 121.7(11) . . ?
C16 C15 N4 123.0(13) . . ?
C14 C15 N4 115.3(12) . . ?
C6 C5 C4 121.0(13) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C15 C14 C13 117.9(11) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C9 C10 C1 119.4(13) . . ?
C9 C10 H10 120.3 . . ?
C1 C10 H10 120.3 . . ?
C2 C1 C10 119.6(12) . . ?
C2 C1 H1A 120.2 . . ?
C10 C1 H1A 120.2 . . ?
C10 C9 C8 116.2(13) . . ?
C10 C9 C4 121.8(14) . . ?
C8 C9 C4 121.9(13) . . ?
C12 C17 C16 123.9(12) . . ?
C12 C17 N3 119.9(11) . . ?
C16 C17 N3 116.3(12) . . ?
C9 C8 C7 120.5(14) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
O1 C2 C3 120.4(13) . . ?
O1 C2 C1 117.0(12) . . ?
C3 C2 C1 122.7(13) . . ?
C17 C16 C15 118.2(12) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C5 C6 C7 128.3(14) . . ?
C5 C6 H6 115.8 . . ?
C7 C6 H6 115.8 . . ?
C12 C13 C14 119.0(13) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C17 C12 N2 127.6(12) . . ?
C17 C12 C13 119.2(13) . . ?
N2 C12 C13 113.1(12) . . ?
C6 C7 C8 113.4(12) . . ?
C6 C7 H7 123.3 . . ?
C8 C7 H7 123.3 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.154
