# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_XS_61_2021_JP585_ether
_database_code_depnum_ccdc_archive 'CCDC 2141407'
loop_
_audit_author_name
_audit_author_address
'Clara Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H20 N2 O6'
_chemical_formula_sum            'C19 H20 N2 O6'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         372.37

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

_cell_length_a                   6.4061(14)
_cell_length_b                   11.990(3)
_cell_length_c                   12.381(3)
_cell_angle_alpha                96.571(8)
_cell_angle_beta                 104.937(6)
_cell_angle_gamma                105.103(5)
_cell_volume                     870.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1371
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      24.82
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9545
_diffrn_reflns_av_unetI/netI     0.1355
_diffrn_reflns_av_R_equivalents  0.1270
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.728
_diffrn_reflns_theta_max         25.421
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3202
_reflns_number_gt                1713
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'WinGX and enCIFer'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+0.1031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     252
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1650
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5321(6) 0.1302(3) 0.6163(3) 0.0246(9) Uani 1 1 d . . . . .
C2 C 0.7341(7) 0.3271(3) 0.6651(3) 0.0257(9) Uani 1 1 d . . . . .
C3 C 0.5332(6) 0.3186(3) 0.5683(3) 0.0229(9) Uani 1 1 d . . . . .
H3 H 0.574574 0.355842 0.507218 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3505(6) 0.3624(3) 0.6081(3) 0.0225(9) Uani 1 1 d . . . . .
C5 C 0.1711(6) 0.3717(3) 0.5037(3) 0.0274(10) Uani 1 1 d . . . . .
H5A H 0.239409 0.416636 0.454554 0.033 Uiso 1 1 calc R U . . .
H5B H 0.064121 0.407075 0.525358 0.033 Uiso 1 1 calc R U . . .
C6 C 0.0573(6) 0.2404(3) 0.4462(3) 0.0246(9) Uani 1 1 d . . . . .
C7 C 0.1743(6) 0.1792(3) 0.5361(3) 0.0238(9) Uani 1 1 d . . . . .
H7 H 0.082102 0.099645 0.535329 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4104(6) 0.1861(3) 0.5286(3) 0.0207(9) Uani 1 1 d . . . . .
H8 H 0.409867 0.156210 0.451438 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8712(7) 0.1961(4) 0.7906(3) 0.0322(10) Uani 1 1 d . . . . .
H9A H 1.023676 0.246001 0.801176 0.039 Uiso 1 1 calc R U . . .
H9B H 0.870839 0.114736 0.777428 0.039 Uiso 1 1 calc R U . . .
C10 C 0.8036(7) 0.2218(3) 0.8966(3) 0.0294(10) Uani 1 1 d . . . . .
C11 C 0.9316(8) 0.3176(4) 0.9820(3) 0.0416(12) Uani 1 1 d . . . . .
H11 H 1.063383 0.367449 0.974962 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8669(10) 0.3403(4) 1.0773(4) 0.0564(14) Uani 1 1 d . . . . .
H12 H 0.956020 0.405076 1.134523 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6754(10) 0.2699(5) 1.0891(4) 0.0641(16) Uani 1 1 d . . . . .
H13 H 0.633109 0.285783 1.154286 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5432(10) 0.1746(5) 1.0043(4) 0.0709(18) Uani 1 1 d . . . . .
H14 H 0.409982 0.126144 1.011356 0.085 Uiso 1 1 calc R U . . .
C15 C 0.6089(8) 0.1511(4) 0.9087(4) 0.0531(14) Uani 1 1 d . . . . .
H15 H 0.519653 0.086211 0.851622 0.064 Uiso 1 1 calc R U . . .
C16 C 0.4488(6) 0.4694(3) 0.7041(3) 0.0267(10) Uani 1 1 d . . . . .
C17 C 0.4642(7) 0.4512(4) 0.8214(3) 0.0409(12) Uani 1 1 d . . . . .
H17A H 0.405550 0.368737 0.820564 0.061 Uiso 1 1 calc R U . . .
H17B H 0.619729 0.479983 0.867682 0.061 Uiso 1 1 calc R U . . .
H17C H 0.377207 0.493182 0.852311 0.061 Uiso 1 1 calc R U . . .
C18 C 0.0399(7) 0.1126(4) 0.2729(3) 0.0320(10) Uani 1 1 d . . . . .
C19 C 0.1019(10) 0.1077(4) 0.1643(4) 0.0595(15) Uani 1 1 d . . . . .
H19A H 0.173534 0.186122 0.156537 0.089 Uiso 1 1 calc R U . . .
H19B H 0.204503 0.061735 0.165653 0.089 Uiso 1 1 calc R U . . .
H19C H -0.032475 0.072228 0.100975 0.089 Uiso 1 1 calc R U . . .
N1 N 0.7165(5) 0.2169(3) 0.6923(2) 0.0254(8) Uani 1 1 d . . . . .
N2 N 0.1008(6) 0.2204(3) 0.3370(3) 0.0289(8) Uani 1 1 d D . . . .
O1 O 0.4858(5) 0.0281(2) 0.6253(2) 0.0333(7) Uani 1 1 d . . . . .
O2 O 0.8890(4) 0.4153(2) 0.7163(2) 0.0389(8) Uani 1 1 d . . . . .
O3 O 0.2283(4) 0.26080(19) 0.64152(19) 0.0252(7) Uani 1 1 d . . . . .
O4 O 0.5108(5) 0.5650(2) 0.6801(2) 0.0473(9) Uani 1 1 d . . . . .
O5 O -0.1756(4) 0.2126(2) 0.4327(2) 0.0351(8) Uani 1 1 d . . . . .
O6 O -0.0530(5) 0.0256(2) 0.3036(2) 0.0469(9) Uani 1 1 d . . . . .
H200 H 0.180(6) 0.278(3) 0.311(3) 0.047(13) Uiso 1 1 d D . . . .
H500 H -0.235(7) 0.138(3) 0.400(3) 0.035(12) 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
C1 O1 1.207(4) . ?
C1 N1 1.387(4) . ?
C1 C8 1.496(5) . ?
C2 O2 1.216(4) . ?
C2 N1 1.384(5) . ?
C2 C3 1.487(5) . ?
C3 C8 1.534(4) . ?
C3 C4 1.565(5) . ?
C3 H3 0.9800 . ?
C4 O3 1.433(4) . ?
C4 C16 1.516(5) . ?
C4 C5 1.530(5) . ?
C5 C6 1.547(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O5 1.402(4) . ?
C6 N2 1.456(5) . ?
C6 C7 1.544(5) . ?
C7 O3 1.441(4) . ?
C7 C8 1.521(5) . ?
C7 H7 0.9800 . ?
C8 H8 0.9800 . ?
C9 N1 1.449(5) . ?
C9 C10 1.508(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.368(5) . ?
C10 C11 1.377(5) . ?
C11 C12 1.369(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.349(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O4 1.210(4) . ?
C16 C17 1.475(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O6 1.213(4) . ?
C18 N2 1.340(5) . ?
C18 C19 1.496(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 H200 0.883(19) . ?
O5 H500 0.88(4) . ?

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
O1 C1 N1 122.7(4) . . ?
O1 C1 C8 128.6(3) . . ?
N1 C1 C8 108.7(3) . . ?
O2 C2 N1 123.8(4) . . ?
O2 C2 C3 127.2(4) . . ?
N1 C2 C3 109.0(3) . . ?
C2 C3 C8 104.7(3) . . ?
C2 C3 C4 112.4(3) . . ?
C8 C3 C4 101.1(3) . . ?
C2 C3 H3 112.6 . . ?
C8 C3 H3 112.6 . . ?
C4 C3 H3 112.6 . . ?
O3 C4 C16 112.3(3) . . ?
O3 C4 C5 101.5(3) . . ?
C16 C4 C5 116.0(3) . . ?
O3 C4 C3 102.5(3) . . ?
C16 C4 C3 113.9(3) . . ?
C5 C4 C3 109.1(3) . . ?
C4 C5 C6 101.1(3) . . ?
C4 C5 H5A 111.6 . . ?
C6 C5 H5A 111.6 . . ?
C4 C5 H5B 111.6 . . ?
C6 C5 H5B 111.6 . . ?
H5A C5 H5B 109.4 . . ?
O5 C6 N2 111.3(3) . . ?
O5 C6 C7 111.4(3) . . ?
N2 C6 C7 114.2(3) . . ?
O5 C6 C5 108.7(3) . . ?
N2 C6 C5 109.2(3) . . ?
C7 C6 C5 101.4(3) . . ?
O3 C7 C8 100.9(3) . . ?
O3 C7 C6 103.0(3) . . ?
C8 C7 C6 110.1(3) . . ?
O3 C7 H7 113.9 . . ?
C8 C7 H7 113.9 . . ?
C6 C7 H7 113.9 . . ?
C1 C8 C7 111.9(3) . . ?
C1 C8 C3 104.7(3) . . ?
C7 C8 C3 101.7(3) . . ?
C1 C8 H8 112.6 . . ?
C7 C8 H8 112.6 . . ?
C3 C8 H8 112.6 . . ?
N1 C9 C10 110.9(3) . . ?
N1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C15 C10 C11 118.3(4) . . ?
C15 C10 C9 120.3(3) . . ?
C11 C10 C9 121.4(4) . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 119.7(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.9(4) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
O4 C16 C17 123.7(3) . . ?
O4 C16 C4 118.0(3) . . ?
C17 C16 C4 118.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C18 N2 121.5(4) . . ?
O6 C18 C19 123.1(4) . . ?
N2 C18 C19 115.3(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 N1 C1 112.2(3) . . ?
C2 N1 C9 123.4(3) . . ?
C1 N1 C9 124.4(3) . . ?
C18 N2 C6 122.4(3) . . ?
C18 N2 H200 115(3) . . ?
C6 N2 H200 122(3) . . ?
C4 O3 C7 97.0(2) . . ?
C6 O5 H500 106(3) . . ?

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
O2 C2 C3 C8 173.4(3) . . . . ?
N1 C2 C3 C8 -8.4(4) . . . . ?
O2 C2 C3 C4 -77.7(4) . . . . ?
N1 C2 C3 C4 100.5(3) . . . . ?
C2 C3 C4 O3 -83.0(3) . . . . ?
C8 C3 C4 O3 28.2(3) . . . . ?
C2 C3 C4 C16 38.6(4) . . . . ?
C8 C3 C4 C16 149.7(3) . . . . ?
C2 C3 C4 C5 170.0(3) . . . . ?
C8 C3 C4 C5 -78.9(3) . . . . ?
O3 C4 C5 C6 -39.9(3) . . . . ?
C16 C4 C5 C6 -161.9(3) . . . . ?
C3 C4 C5 C6 67.8(3) . . . . ?
C4 C5 C6 O5 123.9(3) . . . . ?
C4 C5 C6 N2 -114.5(3) . . . . ?
C4 C5 C6 C7 6.4(3) . . . . ?
O5 C6 C7 O3 -86.8(3) . . . . ?
N2 C6 C7 O3 145.9(3) . . . . ?
C5 C6 C7 O3 28.6(3) . . . . ?
O5 C6 C7 C8 166.2(3) . . . . ?
N2 C6 C7 C8 39.0(4) . . . . ?
C5 C6 C7 C8 -78.3(3) . . . . ?
O1 C1 C8 C7 64.9(5) . . . . ?
N1 C1 C8 C7 -114.2(3) . . . . ?
O1 C1 C8 C3 174.2(3) . . . . ?
N1 C1 C8 C3 -4.9(4) . . . . ?
O3 C7 C8 C1 70.3(3) . . . . ?
C6 C7 C8 C1 178.7(3) . . . . ?
O3 C7 C8 C3 -40.9(3) . . . . ?
C6 C7 C8 C3 67.4(3) . . . . ?
C2 C3 C8 C1 7.9(3) . . . . ?
C4 C3 C8 C1 -109.0(3) . . . . ?
C2 C3 C8 C7 124.5(3) . . . . ?
C4 C3 C8 C7 7.5(3) . . . . ?
N1 C9 C10 C15 68.5(5) . . . . ?
N1 C9 C10 C11 -109.9(4) . . . . ?
C15 C10 C11 C12 0.9(7) . . . . ?
C9 C10 C11 C12 179.4(4) . . . . ?
C10 C11 C12 C13 -0.6(8) . . . . ?
C11 C12 C13 C14 -0.3(9) . . . . ?
C12 C13 C14 C15 0.8(9) . . . . ?
C11 C10 C15 C14 -0.5(8) . . . . ?
C9 C10 C15 C14 -178.9(5) . . . . ?
C13 C14 C15 C10 -0.4(9) . . . . ?
O3 C4 C16 O4 -163.9(3) . . . . ?
C5 C4 C16 O4 -47.8(5) . . . . ?
C3 C4 C16 O4 80.2(5) . . . . ?
O3 C4 C16 C17 16.2(5) . . . . ?
C5 C4 C16 C17 132.3(4) . . . . ?
C3 C4 C16 C17 -99.7(4) . . . . ?
O2 C2 N1 C1 -176.1(3) . . . . ?
C3 C2 N1 C1 5.6(4) . . . . ?
O2 C2 N1 C9 5.2(5) . . . . ?
C3 C2 N1 C9 -173.1(3) . . . . ?
O1 C1 N1 C2 -179.5(3) . . . . ?
C8 C1 N1 C2 -0.3(4) . . . . ?
O1 C1 N1 C9 -0.8(5) . . . . ?
C8 C1 N1 C9 178.4(3) . . . . ?
C10 C9 N1 C2 82.8(4) . . . . ?
C10 C9 N1 C1 -95.7(4) . . . . ?
O6 C18 N2 C6 -0.8(6) . . . . ?
C19 C18 N2 C6 -178.8(4) . . . . ?
O5 C6 N2 C18 -66.1(5) . . . . ?
C7 C6 N2 C18 61.2(5) . . . . ?
C5 C6 N2 C18 173.9(3) . . . . ?
C16 C4 O3 C7 -176.9(3) . . . . ?
C5 C4 O3 C7 58.6(3) . . . . ?
C3 C4 O3 C7 -54.2(3) . . . . ?
C8 C7 O3 C4 59.7(3) . . . . ?
C6 C7 O3 C4 -54.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O4 0.98 2.59 3.496(5) 154.2 2_666 yes
C5 H5A O4 0.97 2.58 3.447(5) 148.7 2_666 yes
C7 H7 O6 0.98 2.65 3.389(5) 132.9 2_556 yes
C8 H8 O1 0.98 2.62 3.331(4) 129.7 2_656 yes
C8 H8 O5 0.98 2.64 3.133(4) 111.2 1_655 yes
C9 H9A O3 0.97 2.64 3.289(4) 124.9 1_655 yes
C9 H9B O6 0.97 2.54 3.375(5) 144.5 2_656 yes
N2 H200 O4 0.883(19) 2.32(2) 3.148(4) 156(4) 2_666 yes
O5 H500 O1 0.88(4) 2.14(4) 2.932(4) 150(3) 2_556 yes
O5 H500 O6 0.88(4) 2.40(4) 2.990(4) 125(3) . yes
C3 H3 O4 0.98 2.59 3.496(5) 154.2 2_666 yes
C5 H5A O4 0.97 2.58 3.447(5) 148.7 2_666 yes
C7 H7 O6 0.98 2.65 3.389(5) 132.9 2_556 yes
C8 H8 O1 0.98 2.62 3.331(4) 129.7 2_656 yes
C8 H8 O5 0.98 2.64 3.133(4) 111.2 1_655 yes
C9 H9A O3 0.97 2.64 3.289(4) 124.9 1_655 yes
C9 H9B O6 0.97 2.54 3.375(5) 144.5 2_656 yes
N2 H200 O4 0.883(19) 2.32(2) 3.148(4) 156(4) 2_666 yes
O5 H500 O1 0.88(4) 2.14(4) 2.932(4) 150(3) 2_556 yes
O5 H500 O6 0.88(4) 2.40(4) 2.990(4) 125(3) . yes

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.066



