# 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_a-fl5
_database_code_depnum_ccdc_archive 'CCDC 1572656'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 N5 O7'
_chemical_formula_sum            'C25 H21 N5 O7'
_chemical_formula_weight         503.47

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                   9.337(3)
_cell_length_b                   10.612(4)
_cell_length_c                   13.512(5)
_cell_angle_alpha                71.627(4)
_cell_angle_beta                 81.230(5)
_cell_angle_gamma                72.359(5)
_cell_volume                     1208.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4081
_cell_measurement_theta_min      0.963
_cell_measurement_theta_max      0.975

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5009
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS(Sheldrick, 2008)'

_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 Smart Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8261
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         24.84
_reflns_number_total             4081
_reflns_number_gt                2512
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1595P)²+0.8533P] 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         4081
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   0.718
_refine_ls_restrained_S_all      0.718
_refine_ls_shift/su_max          0.001
_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
O7 O 0.2621(2) 0.2927(2) 0.82776(16) 0.0612(6) Uani 1 1 d . . .
N1 N -0.0986(3) 0.5613(2) 0.5884(2) 0.0513(6) Uani 1 1 d . . .
O6 O 0.0277(3) 0.3219(3) 0.8989(2) 0.0880(8) Uani 1 1 d . . .
O1 O 0.2997(2) 0.4776(2) 0.53331(17) 0.0607(6) Uani 1 1 d . . .
O4 O -0.2565(3) 0.3724(3) 0.6951(2) 0.0878(8) Uani 1 1 d . . .
O5 O -0.0390(2) 0.2212(2) 0.7429(2) 0.0723(7) Uani 1 1 d . . .
O3 O -0.6454(4) 1.0724(4) 0.2250(3) 0.1458(15) Uani 1 1 d . . .
C1 C -0.0599(3) 0.6822(3) 0.5663(2) 0.0480(7) Uani 1 1 d . . .
O2 O -0.4125(5) 1.0516(3) 0.1769(3) 0.1105(11) Uani 1 1 d . . .
C3 C 0.1582(3) 0.5592(3) 0.6817(2) 0.0462(7) Uani 1 1 d . . .
N5 N 0.4202(3) 0.5155(2) 0.65200(19) 0.0537(6) Uani 1 1 d . . .
H3 H 0.5109 0.4937 0.6255 0.064 Uiso 1 1 calc R . .
C2 C 0.0513(3) 0.6888(3) 0.6180(2) 0.0472(7) Uani 1 1 d . . .
C25 C 0.4868(5) 0.1958(4) 0.9172(3) 0.0907(12) Uani 1 1 d . . .
H20 H 0.5320 0.1413 0.8700 0.136 Uiso 1 1 calc R . .
H18 H 0.5285 0.1498 0.9841 0.136 Uiso 1 1 calc R . .
H19 H 0.5066 0.2844 0.8900 0.136 Uiso 1 1 calc R . .
C24 C 0.3209(4) 0.2141(4) 0.9288(3) 0.0815(11) Uani 1 1 d . . .
H17 H 0.2995 0.1250 0.9515 0.098 Uiso 1 1 calc R . .
H16 H 0.2749 0.2630 0.9804 0.098 Uiso 1 1 calc R . .
C23 C 0.1141(4) 0.3466(3) 0.8262(2) 0.0557(7) Uani 1 1 d . . .
C4 C 0.0725(3) 0.4495(3) 0.7235(2) 0.0481(7) Uani 1 1 d . . .
C5 C -0.0419(3) 0.4523(3) 0.6729(2) 0.0487(7) Uani 1 1 d . . .
N2 N -0.1341(3) 0.7916(2) 0.49189(19) 0.0541(6) Uani 1 1 d . . .
H2 H -0.0839 0.8482 0.4551 0.065 Uiso 1 1 calc R . .
C6 C -0.2852(3) 0.8227(3) 0.4681(2) 0.0476(7) Uani 1 1 d . . .
C7 C -0.3231(3) 0.8979(3) 0.3680(2) 0.0541(7) Uani 1 1 d . . .
H4 H -0.2501 0.9207 0.3159 0.065 Uiso 1 1 calc R . .
C8 C -0.4725(4) 0.9383(3) 0.3475(3) 0.0627(8) Uani 1 1 d . . .
N3 N -0.5133(5) 1.0277(4) 0.2426(3) 0.0900(10) Uani 1 1 d . . .
C13 C 0.2998(3) 0.5098(3) 0.6121(2) 0.0483(7) Uani 1 1 d . . .
C14 C 0.3813(3) 0.5610(3) 0.7415(2) 0.0516(7) Uani 1 1 d . . .
C15 C 0.4756(4) 0.5788(3) 0.8020(3) 0.0646(9) Uani 1 1 d . . .
H7 H 0.5789 0.5618 0.7860 0.077 Uiso 1 1 calc R . .
C16 C 0.4075(5) 0.6237(4) 0.8883(3) 0.0753(10) Uani 1 1 d . . .
H8 H 0.4669 0.6378 0.9310 0.090 Uiso 1 1 calc R . .
C17 C 0.2557(5) 0.6477(4) 0.9124(3) 0.0788(10) Uani 1 1 d . . .
H9 H 0.2140 0.6769 0.9712 0.095 Uiso 1 1 calc R . .
C18 C 0.1636(4) 0.6291(3) 0.8503(3) 0.0648(9) Uani 1 1 d . . .
H10 H 0.0604 0.6451 0.8666 0.078 Uiso 1 1 calc R . .
C19 C 0.2282(3) 0.5862(3) 0.7638(2) 0.0500(7) Uani 1 1 d . . .
C12 C 0.0696(3) 0.8179(3) 0.6093(2) 0.0502(7) Uani 1 1 d . . .
N4 N 0.0831(3) 0.9247(3) 0.6028(2) 0.0685(7) Uani 1 1 d . . .
C20 C -0.1255(3) 0.3453(3) 0.7047(2) 0.0539(7) Uani 1 1 d . . .
C21 C -0.1127(5) 0.1111(4) 0.7913(5) 0.1071(17) Uani 1 1 d . . .
H12 H -0.2021 0.1442 0.8330 0.128 Uiso 1 1 calc R . .
H11 H -0.1433 0.0837 0.7376 0.128 Uiso 1 1 calc R . .
C22 C -0.0116(7) -0.0046(5) 0.8561(5) 0.1315(19) Uani 1 1 d . . .
H15 H 0.0758 -0.0381 0.8144 0.197 Uiso 1 1 calc R . .
H13 H -0.0608 -0.0763 0.8882 0.197 Uiso 1 1 calc R . .
H14 H 0.0182 0.0229 0.9093 0.197 Uiso 1 1 calc R . .
C9 C -0.5838(4) 0.9047(4) 0.4200(3) 0.0733(10) Uani 1 1 d . . .
H5 H -0.6836 0.9330 0.4029 0.088 Uiso 1 1 calc R . .
C10 C -0.5430(4) 0.8278(3) 0.5187(3) 0.0678(9) Uani 1 1 d . . .
H6 H -0.6160 0.8020 0.5696 0.081 Uiso 1 1 calc R . .
C11 C -0.3957(3) 0.7882(3) 0.5435(3) 0.0572(8) Uani 1 1 d . . .
H25 H -0.3701 0.7378 0.6114 0.069 Uiso 1 1 calc R . .
H1 H -0.158(4) 0.549(4) 0.546(3) 0.078(11) Uiso 1 1 d . . .


_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
O7 C23 1.326(4) . ?
O7 C24 1.448(4) . ?
N1 C1 1.368(4) . ?
N1 C5 1.380(4) . ?
N1 H1 0.91(4) . ?
O6 C23 1.187(4) . ?
O1 C13 1.217(3) . ?
O4 C20 1.187(3) . ?
O5 C20 1.306(3) . ?
O5 C21 1.461(4) . ?
O3 N3 1.211(5) . ?
C1 N2 1.352(4) . ?
C1 C2 1.367(4) . ?
O2 N3 1.220(5) . ?
C3 C19 1.509(4) . ?
C3 C2 1.521(4) . ?
C3 C4 1.525(4) . ?
C3 C13 1.555(4) . ?
N5 C13 1.343(4) . ?
N5 C14 1.398(4) . ?
N5 H3 0.8600 . ?
C2 C12 1.398(4) . ?
C25 C24 1.491(5) . ?
C25 H20 0.9600 . ?
C25 H18 0.9600 . ?
C25 H19 0.9600 . ?
C24 H17 0.9700 . ?
C24 H16 0.9700 . ?
C23 C4 1.491(4) . ?
C4 C5 1.342(4) . ?
C5 C20 1.486(4) . ?
N2 C6 1.411(3) . ?
N2 H2 0.8600 . ?
C6 C7 1.374(4) . ?
C6 C11 1.382(4) . ?
C7 C8 1.373(4) . ?
C7 H4 0.9300 . ?
C8 C9 1.364(5) . ?
C8 N3 1.467(5) . ?
C14 C19 1.375(4) . ?
C14 C15 1.377(4) . ?
C15 C16 1.391(5) . ?
C15 H7 0.9300 . ?
C16 C17 1.368(5) . ?
C16 H8 0.9300 . ?
C17 C18 1.382(5) . ?
C17 H9 0.9300 . ?
C18 C19 1.375(4) . ?
C18 H10 0.9300 . ?
C12 N4 1.152(4) . ?
C21 C22 1.427(7) . ?
C21 H12 0.9700 . ?
C21 H11 0.9700 . ?
C22 H15 0.9600 . ?
C22 H13 0.9600 . ?
C22 H14 0.9600 . ?
C9 C10 1.367(5) . ?
C9 H5 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H6 0.9300 . ?
C11 H25 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
C23 O7 C24 116.5(3) . . ?
C1 N1 C5 120.0(3) . . ?
C1 N1 H1 121(2) . . ?
C5 N1 H1 119(2) . . ?
C20 O5 C21 117.3(3) . . ?
N2 C1 C2 122.4(3) . . ?
N2 C1 N1 117.6(2) . . ?
C2 C1 N1 120.0(3) . . ?
C19 C3 C2 112.5(2) . . ?
C19 C3 C4 114.8(2) . . ?
C2 C3 C4 107.3(2) . . ?
C19 C3 C13 101.2(2) . . ?
C2 C3 C13 110.2(2) . . ?
C4 C3 C13 110.7(2) . . ?
C13 N5 C14 112.3(2) . . ?
C13 N5 H3 123.9 . . ?
C14 N5 H3 123.9 . . ?
C1 C2 C12 118.9(2) . . ?
C1 C2 C3 121.6(2) . . ?
C12 C2 C3 119.5(2) . . ?
C24 C25 H20 109.5 . . ?
C24 C25 H18 109.5 . . ?
H20 C25 H18 109.5 . . ?
C24 C25 H19 109.5 . . ?
H20 C25 H19 109.5 . . ?
H18 C25 H19 109.5 . . ?
O7 C24 C25 107.3(3) . . ?
O7 C24 H17 110.3 . . ?
C25 C24 H17 110.3 . . ?
O7 C24 H16 110.3 . . ?
C25 C24 H16 110.3 . . ?
H17 C24 H16 108.5 . . ?
O6 C23 O7 124.4(3) . . ?
O6 C23 C4 124.7(3) . . ?
O7 C23 C4 110.8(2) . . ?
C5 C4 C23 121.9(3) . . ?
C5 C4 C3 120.9(2) . . ?
C23 C4 C3 117.0(2) . . ?
C4 C5 N1 122.0(3) . . ?
C4 C5 C20 124.4(3) . . ?
N1 C5 C20 113.5(2) . . ?
C1 N2 C6 127.0(2) . . ?
C1 N2 H2 116.5 . . ?
C6 N2 H2 116.5 . . ?
C7 C6 C11 119.9(3) . . ?
C7 C6 N2 117.9(3) . . ?
C11 C6 N2 122.1(3) . . ?
C8 C7 C6 117.7(3) . . ?
C8 C7 H4 121.2 . . ?
C6 C7 H4 121.2 . . ?
C9 C8 C7 123.7(3) . . ?
C9 C8 N3 118.9(3) . . ?
C7 C8 N3 117.3(3) . . ?
O3 N3 O2 123.2(4) . . ?
O3 N3 C8 118.4(4) . . ?
O2 N3 C8 118.4(4) . . ?
O1 C13 N5 126.5(3) . . ?
O1 C13 C3 125.7(2) . . ?
N5 C13 C3 107.7(2) . . ?
C19 C14 C15 122.7(3) . . ?
C19 C14 N5 109.5(2) . . ?
C15 C14 N5 127.8(3) . . ?
C14 C15 C16 116.1(3) . . ?
C14 C15 H7 121.9 . . ?
C16 C15 H7 121.9 . . ?
C17 C16 C15 122.0(3) . . ?
C17 C16 H8 119.0 . . ?
C15 C16 H8 119.0 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H9 119.7 . . ?
C18 C17 H9 119.7 . . ?
C19 C18 C17 118.4(3) . . ?
C19 C18 H10 120.8 . . ?
C17 C18 H10 120.8 . . ?
C18 C19 C14 120.2(3) . . ?
C18 C19 C3 130.6(3) . . ?
C14 C19 C3 109.3(2) . . ?
N4 C12 C2 179.2(3) . . ?
O4 C20 O5 124.9(3) . . ?
O4 C20 C5 122.4(3) . . ?
O5 C20 C5 112.7(3) . . ?
C22 C21 O5 109.8(4) . . ?
C22 C21 H12 109.7 . . ?
O5 C21 H12 109.7 . . ?
C22 C21 H11 109.7 . . ?
O5 C21 H11 109.7 . . ?
H12 C21 H11 108.2 . . ?
C21 C22 H15 109.5 . . ?
C21 C22 H13 109.5 . . ?
H15 C22 H13 109.5 . . ?
C21 C22 H14 109.5 . . ?
H15 C22 H14 109.5 . . ?
H13 C22 H14 109.5 . . ?
C8 C9 C10 117.5(3) . . ?
C8 C9 H5 121.2 . . ?
C10 C9 H5 121.2 . . ?
C9 C10 C11 120.8(3) . . ?
C9 C10 H6 119.6 . . ?
C11 C10 H6 119.6 . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H25 119.8 . . ?
C6 C11 H25 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        24.84
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.039
