# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_YFC_069
_database_code_depnum_ccdc_archive 'CCDC 2253791'
loop_
_audit_author_name
_audit_author_address
'Yasufumi Fuchi'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N5 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         413.39
_chemical_absolute_configuration syn

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.660(2)
_cell_length_b                   6.1601(6)
_cell_length_c                   14.0178(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.573(2)
_cell_angle_gamma                90
_cell_volume                     1886.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4466
_cell_measurement_theta_min      2.8647
_cell_measurement_theta_max      25.3587
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864

_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Tourbo X-ray Source'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4765
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3282
_reflns_number_gt                3250
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0974
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         3282
_refine_ls_number_parameters     278
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+1.1167P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)

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'

_computing_data_collection       'Bruker Instrument Service v2017.5.0.0'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL V6.3.1'
_computing_publication_material  'Generate Report'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.62762(7) 0.2459(3) 0.56994(12) 0.0142(4) Uani d . . . 1 . .
O O4 0.64759(8) -0.0668(3) 0.67421(13) 0.0165(4) Uani d . . . 1 . .
O O2 0.71516(8) -0.2320(3) 0.56279(13) 0.0168(4) Uani d . . . 1 . .
H H2 0.7026 -0.3055 0.6012 0.025 Uiso calc U . R 1 . .
O O5 0.58495(7) -0.2118(3) 0.51258(13) 0.0172(4) Uani d . . . 1 . .
O O6 0.60847(8) 0.9777(3) 0.22174(13) 0.0171(4) Uani d . . . 1 . .
O O1 0.75442(8) 0.3351(3) 0.65546(14) 0.0182(4) Uani d . . . 1 . .
H H1 0.7899 0.2923 0.6652 0.027 Uiso calc U . R 1 . .
N N1 0.59955(9) 0.3124(4) 0.39267(15) 0.0125(4) Uani d . . . 1 . .
N N3 0.49859(9) 0.2900(4) 0.25527(15) 0.0137(4) Uani d . . . 1 . .
N N2 0.64450(9) 0.5463(3) 0.31972(15) 0.0136(4) Uani d . . . 1 . .
N N5 0.57015(9) 0.7200(4) 0.09745(16) 0.0141(4) Uani d . . . 1 . .
N N4 0.48992(9) 0.5166(4) 0.10992(15) 0.0154(4) Uani d . . . 1 . .
C C10 0.58387(10) 0.5143(4) 0.25472(18) 0.0112(5) Uani d . . . 1 . .
C C11 0.54786(11) 0.5871(4) 0.15550(17) 0.0129(5) Uani d . . . 1 . .
C C8 0.65144(11) 0.4243(4) 0.40013(18) 0.0138(5) Uani d . . . 1 . .
H H8 0.689 0.414 0.4584 0.017 Uiso calc U . R 1 . .
C C15 0.63493(11) 0.9214(4) -0.01717(19) 0.0154(5) Uani d . . . 1 . .
H H15 0.6155 0.7859 -0.0414 0.018 Uiso calc U . R 1 . .
C C9 0.55548(11) 0.3672(4) 0.29796(18) 0.0120(5) Uani d . . . 1 . .
C C2 0.67179(10) 0.0822(4) 0.62172(18) 0.0134(5) Uani d . . . 1 . .
C C19 0.66190(11) 1.2123(5) 0.10803(19) 0.0178(5) Uani d . . . 1 . .
H H19 0.6611 1.275 0.1694 0.021 Uiso calc U . R 1 . .
C C13 0.60339(11) 0.9057(4) 0.13802(18) 0.0129(5) Uani d . . . 1 . .
C C3 0.68066(10) -0.0397(4) 0.53329(18) 0.0134(5) Uani d . . . 1 . .
H H3 0.7005 0.0592 0.4988 0.016 Uiso calc U . R 1 . .
C C12 0.46904(11) 0.3736(5) 0.16105(19) 0.0160(5) Uani d . . . 1 . .
H H12 0.4281 0.3257 0.1258 0.019 Uiso calc U . R 1 . .
C C16 0.66514(11) 1.0287(5) -0.07148(18) 0.0176(5) Uani d . . . 1 . .
H H16 0.6662 0.9667 -0.1328 0.021 Uiso calc U . R 1 . .
C C14 0.63317(10) 1.0130(4) 0.07295(18) 0.0139(5) Uani d . . . 1 . .
C C4 0.61242(11) -0.0643(4) 0.46407(18) 0.0141(5) Uani d . . . 1 . .
H H4 0.606 -0.1099 0.3922 0.017 Uiso calc U . R 1 . .
C C1 0.72720(11) 0.1897(4) 0.70237(18) 0.0159(5) Uani d . . . 1 . .
H H1A 0.7146 0.2689 0.7524 0.019 Uiso calc U . R 1 . .
H H1B 0.7573 0.0774 0.7406 0.019 Uiso calc U . R 1 . .
C C6 0.58725(11) -0.1373(4) 0.61044(19) 0.0169(5) Uani d . . . 1 . .
H H6 0.5579 -0.014 0.5997 0.02 Uiso calc U . R 1 . .
C C5 0.59084(10) 0.1692(4) 0.46845(18) 0.0130(5) Uani d . . . 1 . .
H H5 0.5467 0.1687 0.459 0.016 Uiso calc U . R 1 . .
C C18 0.69144(11) 1.3183(5) 0.0533(2) 0.0214(6) Uani d . . . 1 . .
H H18 0.7103 1.4549 0.0767 0.026 Uiso calc U . R 1 . .
C C17 0.69361(11) 1.2263(5) -0.0358(2) 0.0190(6) Uani d . . . 1 . .
H H17 0.7146 1.2987 -0.0722 0.023 Uiso calc U . R 1 . .
C C7 0.56901(13) -0.3205(5) 0.6631(2) 0.0241(6) Uani d . . . 1 . .
H H7A 0.5974 -0.4421 0.6729 0.036 Uiso calc U . R 1 . .
H H7B 0.5274 -0.3675 0.6204 0.036 Uiso calc U . R 1 . .
H H7C 0.5704 -0.2714 0.7305 0.036 Uiso calc U . R 1 . .
H H20 0.5600(13) 0.687(6) 0.033(3) 0.018(8) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 C2 . 1.433(3) ?
O3 C5 . 1.433(3) ?
O4 C2 . 1.426(3) ?
O4 C6 . 1.430(3) ?
O2 C3 . 1.408(3) ?
O2 H2 . 0.84 ?
O5 C6 . 1.428(3) ?
O5 C4 . 1.432(3) ?
O6 C13 . 1.217(3) ?
O1 C1 . 1.405(3) ?
O1 H1 . 0.84 ?
N1 C8 . 1.377(3) ?
N1 C9 . 1.379(3) ?
N1 C5 . 1.455(3) ?
N3 C9 . 1.333(3) ?
N3 C12 . 1.338(3) ?
N2 C8 . 1.312(3) ?
N2 C10 . 1.387(3) ?
N5 C13 . 1.381(3) ?
N5 C11 . 1.393(3) ?
N5 H20 . 0.86(3) ?
N4 C11 . 1.343(3) ?
N4 C12 . 1.344(3) ?
C10 C11 . 1.397(3) ?
C10 C9 . 1.397(3) ?
C8 H8 . 0.95 ?
C15 C16 . 1.395(4) ?
C15 C14 . 1.399(3) ?
C15 H15 . 0.95 ?
C2 C1 . 1.516(3) ?
C2 C3 . 1.531(3) ?
C19 C18 . 1.384(4) ?
C19 C14 . 1.398(4) ?
C19 H19 . 0.95 ?
C13 C14 . 1.503(3) ?
C3 C4 . 1.539(3) ?
C3 H3 . 1.0 ?
C12 H12 . 0.95 ?
C16 C17 . 1.388(4) ?
C16 H16 . 0.95 ?
C4 C5 . 1.535(4) ?
C4 H4 . 1.0 ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C6 C7 . 1.500(4) ?
C6 H6 . 1.0 ?
C5 H5 . 1.0 ?
C18 C17 . 1.389(4) ?
C18 H18 . 0.95 ?
C17 H17 . 0.95 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O3 C5 . . 108.52(18) ?
C2 O4 C6 . . 112.02(17) ?
C3 O2 H2 . . 109.5 ?
C6 O5 C4 . . 113.30(19) ?
C1 O1 H1 . . 109.5 ?
C8 N1 C9 . . 105.9(2) ?
C8 N1 C5 . . 128.3(2) ?
C9 N1 C5 . . 125.78(19) ?
C9 N3 C12 . . 111.2(2) ?
C8 N2 C10 . . 103.9(2) ?
C13 N5 C11 . . 122.0(2) ?
C13 N5 H20 . . 121.(2) ?
C11 N5 H20 . . 117.(2) ?
C11 N4 C12 . . 118.4(2) ?
N2 C10 C11 . . 133.6(2) ?
N2 C10 C9 . . 110.8(2) ?
C11 C10 C9 . . 115.4(2) ?
N4 C11 N5 . . 117.3(2) ?
N4 C11 C10 . . 119.4(2) ?
N5 C11 C10 . . 123.2(2) ?
N2 C8 N1 . . 114.1(2) ?
N2 C8 H8 . . 123.0 ?
N1 C8 H8 . . 123.0 ?
C16 C15 C14 . . 120.1(2) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
N3 C9 N1 . . 127.2(2) ?
N3 C9 C10 . . 127.4(2) ?
N1 C9 C10 . . 105.3(2) ?
O4 C2 O3 . . 110.78(18) ?
O4 C2 C1 . . 107.46(18) ?
O3 C2 C1 . . 108.9(2) ?
O4 C2 C3 . . 108.0(2) ?
O3 C2 C3 . . 103.59(17) ?
C1 C2 C3 . . 118.04(19) ?
C18 C19 C14 . . 120.0(2) ?
C18 C19 H19 . . 120.0 ?
C14 C19 H19 . . 120.0 ?
O6 C13 N5 . . 121.9(2) ?
O6 C13 C14 . . 122.0(2) ?
N5 C13 C14 . . 116.1(2) ?
O2 C3 C2 . . 114.78(19) ?
O2 C3 C4 . . 116.9(2) ?
C2 C3 C4 . . 97.00(18) ?
O2 C3 H3 . . 109.2 ?
C2 C3 H3 . . 109.2 ?
C4 C3 H3 . . 109.2 ?
N3 C12 N4 . . 128.3(2) ?
N3 C12 H12 . . 115.9 ?
N4 C12 H12 . . 115.9 ?
C17 C16 C15 . . 119.9(2) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C19 C14 C15 . . 119.5(2) ?
C19 C14 C13 . . 116.8(2) ?
C15 C14 C13 . . 123.7(2) ?
O5 C4 C5 . . 110.92(18) ?
O5 C4 C3 . . 108.70(19) ?
C5 C4 C3 . . 99.6(2) ?
O5 C4 H4 . . 112.3 ?
C5 C4 H4 . . 112.3 ?
C3 C4 H4 . . 112.3 ?
O1 C1 C2 . . 110.50(19) ?
O1 C1 H1A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.1 ?
O5 C6 O4 . . 111.02(19) ?
O5 C6 C7 . . 108.6(2) ?
O4 C6 C7 . . 109.1(2) ?
O5 C6 H6 . . 109.4 ?
O4 C6 H6 . . 109.4 ?
C7 C6 H6 . . 109.4 ?
O3 C5 N1 . . 108.82(19) ?
O3 C5 C4 . . 105.31(18) ?
N1 C5 C4 . . 113.35(19) ?
O3 C5 H5 . . 109.7 ?
N1 C5 H5 . . 109.7 ?
C4 C5 H5 . . 109.7 ?
C19 C18 C17 . . 120.4(3) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C16 C17 C18 . . 120.1(2) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?

