# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_dzt_a75
_database_code_depnum_ccdc_archive 'CCDC 2126314'
loop_
_audit_author_name
_audit_author_address
'Li Xiaonian'
;Chinese acadmey sciences
China
;
_audit_update_record             
;
2021-12-05 deposited with the CCDC.	2022-03-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H16 N2 O3'
_chemical_formula_sum            'C13 H16 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         248.28
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.0646(2)
_cell_length_b                   13.3250(3)
_cell_length_c                   20.6396(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2492.97(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      3.9488
_cell_measurement_theta_max      72.1233
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.530
_exptl_crystal_size_min          0.470
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056

_exptl_absorpt_coefficient_mu    0.782
_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  0.58
_exptl_absorpt_correction_T_max  0.71

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            27321
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_theta_min         3.95
_diffrn_reflns_theta_max         72.12
_diffrn_reflns_theta_full        72.12
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             4905
_reflns_number_gt                4889
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0681
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         4905
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0330P)²+0.6514P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0153(6)
_refine_ls_abs_structure_details 
;

Flack x determined using 2084 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

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 O1 -0.02825(13) 0.22183(8) 0.54811(5) 0.0153(3) Uani d . . . 1 . .
O O2 -0.01597(14) 0.50516(9) 0.73617(6) 0.0190(3) Uani d . . . 1 . .
O O3 0.24992(12) 0.29251(10) 0.60644(6) 0.0171(3) Uani d . . . 1 . .
H H29 0.30737 0.282184 0.637672 0.026 Uiso calc U . R 1 . .
O O4 0.79887(13) 0.24753(9) 0.90639(6) 0.0169(3) Uani d . . . 1 . .
O O5 0.35806(14) 0.28989(10) 0.73089(6) 0.0207(3) Uani d . . . 1 . .
O O6 0.65685(12) 0.07435(9) 0.84197(6) 0.0158(2) Uani d . . . 1 . .
H H31 0.5728 0.055179 0.853827 0.024 Uiso calc U . R 1 . .
N N1 0.10240(16) 0.38829(11) 0.67587(7) 0.0152(3) Uani d . . . 1 . .
H H30 0.185737 0.402318 0.695781 0.018 Uiso calc U . R 1 . .
N N2 -0.40056(17) 0.47157(11) 0.62840(8) 0.0207(3) Uani d . . . 1 . .
N N3 0.52013(16) 0.54416(11) 0.82133(7) 0.0188(3) Uani d . . . 1 . .
N N4 0.52596(15) 0.19220(10) 0.78133(6) 0.0138(3) Uani d . . . 1 . .
H H32 0.493838 0.140004 0.759344 0.017 Uiso calc U . R 1 . .
C C1 -0.1245(2) 0.07687(15) 0.60601(11) 0.0306(5) Uani d . . . 1 . .
H H4 -0.212432 0.115623 0.61776 0.046 Uiso calc U . R 1 . .
H H3 -0.102383 0.028532 0.640446 0.046 Uiso calc U . R 1 . .
H H1 -0.142653 0.040878 0.565375 0.046 Uiso calc U . R 1 . .
C C2 0.00503(19) 0.14727(12) 0.59743(8) 0.0168(3) Uani d . . . 1 . .
H H5 0.092962 0.107521 0.583375 0.02 Uiso calc U . R 1 . .
C C3 0.00192(18) 0.32138(12) 0.57137(7) 0.0130(3) Uani d . . . 1 . .
C C4 -0.14135(18) 0.37042(12) 0.59308(8) 0.0135(3) Uani d . . . 1 . .
C C5 -0.14627(18) 0.43162(12) 0.64805(8) 0.0142(3) Uani d . . . 1 . .
C C6 -0.27735(19) 0.48046(13) 0.66324(9) 0.0175(3) Uani d . . . 1 . .
H H2 -0.279234 0.522419 0.700445 0.021 Uiso calc U . R 1 . .
C C7 0.04496(18) 0.20677(13) 0.65777(8) 0.0159(3) Uani d . . . 1 . .
H H13 0.120787 0.171535 0.683734 0.019 Uiso calc U . R 1 . .
H H14 -0.042925 0.218953 0.68514 0.019 Uiso calc U . R 1 . .
C C8 0.10516(18) 0.30494(12) 0.62988(7) 0.0133(3) Uani d . . . 1 . .
C C9 -0.01485(18) 0.44571(12) 0.69082(8) 0.0142(3) Uani d . . . 1 . .
C C10 0.06965(19) 0.38036(13) 0.51487(8) 0.0167(3) Uani d . . . 1 . .
H H7 0.166217 0.350005 0.50401 0.02 Uiso calc U . R 1 . .
H H6 0.004936 0.372612 0.476554 0.02 Uiso calc U . R 1 . .
C C11 0.0926(2) 0.49237(13) 0.52728(9) 0.0206(4) Uani d . . . 1 . .
H H8 -0.002109 0.523578 0.53814 0.031 Uiso calc U . R 1 . .
H H9 0.1331 0.524008 0.488283 0.031 Uiso calc U . R 1 . .
H H10 0.161579 0.501329 0.563391 0.031 Uiso calc U . R 1 . .
C C12 -0.2701(2) 0.35993(13) 0.55711(9) 0.0182(4) Uani d . . . 1 . .
H H11 -0.27146 0.318717 0.51956 0.022 Uiso calc U . R 1 . .
C C13 -0.3960(2) 0.41009(13) 0.57654(9) 0.0204(4) Uani d . . . 1 . .
H H12 -0.483788 0.400776 0.552128 0.024 Uiso calc U . R 1 . .
C C14 1.0216(2) 0.29017(16) 0.84745(10) 0.0272(4) Uani d . . . 1 . .
H H17 0.981076 0.353981 0.831937 0.041 Uiso calc U . R 1 . .
H H15 1.093849 0.264885 0.816116 0.041 Uiso calc U . R 1 . .
H H16 1.069891 0.300577 0.889398 0.041 Uiso calc U . R 1 . .
C C15 0.89830(18) 0.21473(13) 0.85499(8) 0.0165(3) Uani d . . . 1 . .
H H28 0.941441 0.148238 0.867056 0.02 Uiso calc U . R 1 . .
C C16 0.64930(17) 0.24715(12) 0.88478(8) 0.0131(3) Uani d . . . 1 . .
C C17 0.60575(18) 0.35219(12) 0.86310(8) 0.0134(3) Uani d . . . 1 . .
C C18 0.50715(18) 0.36534(12) 0.81212(8) 0.0145(3) Uani d . . . 1 . .
C C19 0.46652(19) 0.46167(13) 0.79372(8) 0.0175(3) Uani d . . . 1 . .
H H20 0.396849 0.469048 0.759672 0.021 Uiso calc U . R 1 . .
C C20 0.66039(18) 0.43800(13) 0.89285(8) 0.0168(3) Uani d . . . 1 . .
H H18 0.726834 0.432802 0.928288 0.02 Uiso calc U . R 1 . .
C C21 0.61678(19) 0.53120(13) 0.87021(8) 0.0171(3) Uani d . . . 1 . .
H H19 0.657221 0.589199 0.890235 0.021 Uiso calc U . R 1 . .
C C22 0.45649(18) 0.27944(13) 0.77201(8) 0.0148(3) Uani d . . . 1 . .
C C23 0.65114(18) 0.17602(12) 0.82507(8) 0.0131(3) Uani d . . . 1 . .
C C24 0.80074(17) 0.20156(13) 0.79554(8) 0.0141(3) Uani d . . . 1 . .
H H22 0.836979 0.146412 0.767619 0.017 Uiso calc U . R 1 . .
H H21 0.795771 0.264152 0.769793 0.017 Uiso calc U . R 1 . .
C C25 0.55450(19) 0.21335(14) 0.94224(8) 0.0182(4) Uani d . . . 1 . .
H H26 0.581324 0.143296 0.953041 0.022 Uiso calc U . R 1 . .
H H27 0.580049 0.25545 0.980133 0.022 Uiso calc U . R 1 . .
C C26 0.3876(2) 0.21824(14) 0.93228(9) 0.0213(4) Uani d . . . 1 . .
H H25 0.358154 0.287882 0.924217 0.032 Uiso calc U . R 1 . .
H H24 0.337633 0.193362 0.971195 0.032 Uiso calc U . R 1 . .
H H23 0.360125 0.176609 0.895054 0.032 Uiso calc U . R 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
O1 C3 . 1.4370(18) ?
O1 C2 . 1.4540(19) ?
O2 C9 . 1.226(2) ?
O3 C8 . 1.4083(19) ?
O3 H29 . 0.84 ?
O4 C16 . 1.4273(19) ?
O4 C15 . 1.459(2) ?
O5 C22 . 1.239(2) ?
O6 C23 . 1.3999(19) ?
O6 H31 . 0.84 ?
N1 C9 . 1.345(2) ?
N1 C8 . 1.461(2) ?
N1 H30 . 0.88 ?
N2 C6 . 1.334(2) ?
N2 C13 . 1.348(2) ?
N3 C19 . 1.330(2) ?
N3 C21 . 1.347(2) ?
N4 C22 . 1.336(2) ?
N4 C23 . 1.466(2) ?
N4 H32 . 0.88 ?
C1 C2 . 1.513(3) ?
C1 H4 . 0.98 ?
C1 H3 . 0.98 ?
C1 H1 . 0.98 ?
C2 C7 . 1.520(2) ?
C2 H5 . 1.0 ?
C3 C4 . 1.521(2) ?
C3 C10 . 1.534(2) ?
C3 C8 . 1.543(2) ?
C4 C12 . 1.390(2) ?
C4 C5 . 1.398(2) ?
C5 C6 . 1.391(2) ?
C5 C9 . 1.495(2) ?
C6 H2 . 0.95 ?
C7 C8 . 1.530(2) ?
C7 H13 . 0.99 ?
C7 H14 . 0.99 ?
C10 C11 . 1.529(2) ?
C10 H7 . 0.99 ?
C10 H6 . 0.99 ?
C11 H8 . 0.98 ?
C11 H9 . 0.98 ?
C11 H10 . 0.98 ?
C12 C13 . 1.382(2) ?
C12 H11 . 0.95 ?
C13 H12 . 0.95 ?
C14 C15 . 1.511(2) ?
C14 H17 . 0.98 ?
C14 H15 . 0.98 ?
C14 H16 . 0.98 ?
C15 C24 . 1.522(2) ?
C15 H28 . 1.0 ?
C16 C17 . 1.522(2) ?
C16 C25 . 1.532(2) ?
C16 C23 . 1.555(2) ?
C17 C20 . 1.389(2) ?
C17 C18 . 1.392(2) ?
C18 C19 . 1.388(2) ?
C18 C22 . 1.485(2) ?
C19 H20 . 0.95 ?
C20 C21 . 1.385(2) ?
C20 H18 . 0.95 ?
C21 H19 . 0.95 ?
C23 C24 . 1.525(2) ?
C24 H22 . 0.99 ?
C24 H21 . 0.99 ?
C25 C26 . 1.528(2) ?
C25 H26 . 0.99 ?
C25 H27 . 0.99 ?
C26 H25 . 0.98 ?
C26 H24 . 0.98 ?
C26 H23 . 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
C3 O1 C2 . . 110.94(11) ?
C8 O3 H29 . . 109.5 ?
C16 O4 C15 . . 111.00(12) ?
C23 O6 H31 . . 109.5 ?
C9 N1 C8 . . 126.49(14) ?
C9 N1 H30 . . 116.8 ?
C8 N1 H30 . . 116.8 ?
C6 N2 C13 . . 117.15(15) ?
C19 N3 C21 . . 116.90(15) ?
C22 N4 C23 . . 125.55(14) ?
C22 N4 H32 . . 117.2 ?
C23 N4 H32 . . 117.2 ?
C2 C1 H4 . . 109.5 ?
C2 C1 H3 . . 109.5 ?
H4 C1 H3 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H4 C1 H1 . . 109.5 ?
H3 C1 H1 . . 109.5 ?
O1 C2 C1 . . 110.15(14) ?
O1 C2 C7 . . 105.46(13) ?
C1 C2 C7 . . 114.34(15) ?
O1 C2 H5 . . 108.9 ?
C1 C2 H5 . . 108.9 ?
C7 C2 H5 . . 108.9 ?
O1 C3 C4 . . 109.42(13) ?
O1 C3 C10 . . 107.17(12) ?
C4 C3 C10 . . 110.21(13) ?
O1 C3 C8 . . 104.22(12) ?
C4 C3 C8 . . 110.37(13) ?
C10 C3 C8 . . 115.13(13) ?
C12 C4 C5 . . 117.73(15) ?
C12 C4 C3 . . 121.07(14) ?
C5 C4 C3 . . 121.12(14) ?
C6 C5 C4 . . 118.90(15) ?
C6 C5 C9 . . 119.29(15) ?
C4 C5 C9 . . 121.81(15) ?
N2 C6 C5 . . 123.53(16) ?
N2 C6 H2 . . 118.2 ?
C5 C6 H2 . . 118.2 ?
C2 C7 C8 . . 102.86(13) ?
C2 C7 H13 . . 111.2 ?
C8 C7 H13 . . 111.2 ?
C2 C7 H14 . . 111.2 ?
C8 C7 H14 . . 111.2 ?
H13 C7 H14 . . 109.1 ?
O3 C8 N1 . . 109.18(13) ?
O3 C8 C7 . . 111.16(13) ?
N1 C8 C7 . . 113.54(13) ?
O3 C8 C3 . . 108.23(12) ?
N1 C8 C3 . . 112.96(13) ?
C7 C8 C3 . . 101.51(13) ?
O2 C9 N1 . . 123.29(16) ?
O2 C9 C5 . . 121.69(15) ?
N1 C9 C5 . . 115.01(14) ?
C11 C10 C3 . . 115.29(14) ?
C11 C10 H7 . . 108.5 ?
C3 C10 H7 . . 108.5 ?
C11 C10 H6 . . 108.5 ?
C3 C10 H6 . . 108.5 ?
H7 C10 H6 . . 107.5 ?
C10 C11 H8 . . 109.5 ?
C10 C11 H9 . . 109.5 ?
H8 C11 H9 . . 109.5 ?
C10 C11 H10 . . 109.5 ?
H8 C11 H10 . . 109.5 ?
H9 C11 H10 . . 109.5 ?
C13 C12 C4 . . 119.32(15) ?
C13 C12 H11 . . 120.3 ?
C4 C12 H11 . . 120.3 ?
N2 C13 C12 . . 123.32(16) ?
N2 C13 H12 . . 118.3 ?
C12 C13 H12 . . 118.3 ?
C15 C14 H17 . . 109.5 ?
C15 C14 H15 . . 109.5 ?
H17 C14 H15 . . 109.5 ?
C15 C14 H16 . . 109.5 ?
H17 C14 H16 . . 109.5 ?
H15 C14 H16 . . 109.5 ?
O4 C15 C14 . . 109.42(15) ?
O4 C15 C24 . . 105.17(13) ?
C14 C15 C24 . . 115.04(14) ?
O4 C15 H28 . . 109.0 ?
C14 C15 H28 . . 109.0 ?
C24 C15 H28 . . 109.0 ?
O4 C16 C17 . . 109.58(13) ?
O4 C16 C25 . . 106.97(12) ?
C17 C16 C25 . . 110.64(13) ?
O4 C16 C23 . . 103.87(12) ?
C17 C16 C23 . . 109.30(12) ?
C25 C16 C23 . . 116.12(14) ?
C20 C17 C18 . . 117.36(15) ?
C20 C17 C16 . . 122.32(14) ?
C18 C17 C16 . . 120.31(14) ?
C19 C18 C17 . . 119.57(15) ?
C19 C18 C22 . . 118.56(15) ?
C17 C18 C22 . . 121.53(14) ?
N3 C19 C18 . . 123.37(16) ?
N3 C19 H20 . . 118.3 ?
C18 C19 H20 . . 118.3 ?
C21 C20 C17 . . 119.16(15) ?
C21 C20 H18 . . 120.4 ?
C17 C20 H18 . . 120.4 ?
N3 C21 C20 . . 123.60(15) ?
N3 C21 H19 . . 118.2 ?
C20 C21 H19 . . 118.2 ?
O5 C22 N4 . . 122.40(15) ?
O5 C22 C18 . . 121.17(15) ?
N4 C22 C18 . . 116.39(14) ?
O6 C23 N4 . . 108.93(13) ?
O6 C23 C24 . . 106.42(13) ?
N4 C23 C24 . . 114.17(13) ?
O6 C23 C16 . . 113.13(13) ?
N4 C23 C16 . . 112.97(13) ?
C24 C23 C16 . . 100.96(13) ?
C15 C24 C23 . . 102.72(13) ?
C15 C24 H22 . . 111.2 ?
C23 C24 H22 . . 111.2 ?
C15 C24 H21 . . 111.2 ?
C23 C24 H21 . . 111.2 ?
H22 C24 H21 . . 109.1 ?
C26 C25 C16 . . 116.01(14) ?
C26 C25 H26 . . 108.3 ?
C16 C25 H26 . . 108.3 ?
C26 C25 H27 . . 108.3 ?
C16 C25 H27 . . 108.3 ?
H26 C25 H27 . . 107.4 ?
C25 C26 H25 . . 109.5 ?
C25 C26 H24 . . 109.5 ?
H25 C26 H24 . . 109.5 ?
C25 C26 H23 . . 109.5 ?
H25 C26 H23 . . 109.5 ?
H24 C26 H23 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 O1 C2 C1 . . . . 129.50(16) ?
C3 O1 C2 C7 . . . . 5.64(17) ?
C2 O1 C3 C4 . . . . -99.51(14) ?
C2 O1 C3 C10 . . . . 141.01(13) ?
C2 O1 C3 C8 . . . . 18.53(16) ?
O1 C3 C4 C12 . . . . -41.8(2) ?
C10 C3 C4 C12 . . . . 75.83(19) ?
C8 C3 C4 C12 . . . . -155.90(15) ?
O1 C3 C4 C5 . . . . 141.48(14) ?
C10 C3 C4 C5 . . . . -100.92(17) ?
C8 C3 C4 C5 . . . . 27.4(2) ?
C12 C4 C5 C6 . . . . -1.4(2) ?
C3 C4 C5 C6 . . . . 175.43(15) ?
C12 C4 C5 C9 . . . . 178.48(15) ?
C3 C4 C5 C9 . . . . -4.7(2) ?
C13 N2 C6 C5 . . . . 1.3(3) ?
C4 C5 C6 N2 . . . . 0.6(3) ?
C9 C5 C6 N2 . . . . -179.26(15) ?
O1 C2 C7 C8 . . . . -27.55(16) ?
C1 C2 C7 C8 . . . . -148.71(15) ?
C9 N1 C8 O3 . . . . 154.67(15) ?
C9 N1 C8 C7 . . . . -80.69(19) ?
C9 N1 C8 C3 . . . . 34.2(2) ?
C2 C7 C8 O3 . . . . -77.21(15) ?
C2 C7 C8 N1 . . . . 159.23(13) ?
C2 C7 C8 C3 . . . . 37.70(15) ?
O1 C3 C8 O3 . . . . 82.33(15) ?
C4 C3 C8 O3 . . . . -160.29(13) ?
C10 C3 C8 O3 . . . . -34.75(18) ?
O1 C3 C8 N1 . . . . -156.66(13) ?
C4 C3 C8 N1 . . . . -39.28(18) ?
C10 C3 C8 N1 . . . . 86.26(17) ?
O1 C3 C8 C7 . . . . -34.74(15) ?
C4 C3 C8 C7 . . . . 82.65(15) ?
C10 C3 C8 C7 . . . . -151.82(13) ?
C8 N1 C9 O2 . . . . 169.41(15) ?
C8 N1 C9 C5 . . . . -10.2(2) ?
C6 C5 C9 O2 . . . . -5.7(2) ?
C4 C5 C9 O2 . . . . 174.44(15) ?
C6 C5 C9 N1 . . . . 173.96(15) ?
C4 C5 C9 N1 . . . . -5.9(2) ?
O1 C3 C10 C11 . . . . 172.87(14) ?
C4 C3 C10 C11 . . . . 53.89(19) ?
C8 C3 C10 C11 . . . . -71.73(19) ?
C5 C4 C12 C13 . . . . 0.3(2) ?
C3 C4 C12 C13 . . . . -176.50(15) ?
C6 N2 C13 C12 . . . . -2.4(3) ?
C4 C12 C13 N2 . . . . 1.6(3) ?
C16 O4 C15 C14 . . . . 128.96(15) ?
C16 O4 C15 C24 . . . . 4.86(17) ?
C15 O4 C16 C17 . . . . -96.65(15) ?
C15 O4 C16 C25 . . . . 143.37(14) ?
C15 O4 C16 C23 . . . . 20.03(16) ?
O4 C16 C17 C20 . . . . -34.1(2) ?
C25 C16 C17 C20 . . . . 83.56(19) ?
C23 C16 C17 C20 . . . . -147.36(15) ?
O4 C16 C17 C18 . . . . 146.32(14) ?
C25 C16 C17 C18 . . . . -95.97(17) ?
C23 C16 C17 C18 . . . . 33.1(2) ?
C20 C17 C18 C19 . . . . -0.7(2) ?
C16 C17 C18 C19 . . . . 178.83(15) ?
C20 C17 C18 C22 . . . . 172.48(15) ?
C16 C17 C18 C22 . . . . -8.0(2) ?
C21 N3 C19 C18 . . . . -1.1(3) ?
C17 C18 C19 N3 . . . . 1.8(3) ?
C22 C18 C19 N3 . . . . -171.56(16) ?
C18 C17 C20 C21 . . . . -1.0(2) ?
C16 C17 C20 C21 . . . . 179.50(15) ?
C19 N3 C21 C20 . . . . -0.7(3) ?
C17 C20 C21 N3 . . . . 1.8(3) ?
C23 N4 C22 O5 . . . . 174.71(15) ?
C23 N4 C22 C18 . . . . -3.1(2) ?
C19 C18 C22 O5 . . . . -13.9(2) ?
C17 C18 C22 O5 . . . . 172.87(16) ?
C19 C18 C22 N4 . . . . 164.03(16) ?
C17 C18 C22 N4 . . . . -9.2(2) ?
C22 N4 C23 O6 . . . . 156.69(15) ?
C22 N4 C23 C24 . . . . -84.5(2) ?
C22 N4 C23 C16 . . . . 30.1(2) ?
O4 C16 C23 O6 . . . . 76.81(16) ?
C17 C16 C23 O6 . . . . -166.31(13) ?
C25 C16 C23 O6 . . . . -40.32(19) ?
O4 C16 C23 N4 . . . . -158.85(12) ?
C17 C16 C23 N4 . . . . -41.97(17) ?
C25 C16 C23 N4 . . . . 84.02(17) ?
O4 C16 C23 C24 . . . . -36.51(15) ?
C17 C16 C23 C24 . . . . 80.38(14) ?
C25 C16 C23 C24 . . . . -153.63(13) ?
O4 C15 C24 C23 . . . . -28.09(16) ?
C14 C15 C24 C23 . . . . -148.55(16) ?
O6 C23 C24 C15 . . . . -79.34(15) ?
N4 C23 C24 C15 . . . . 160.47(13) ?
C16 C23 C24 C15 . . . . 38.96(15) ?
O4 C16 C25 C26 . . . . 173.64(15) ?
C17 C16 C25 C26 . . . . 54.3(2) ?
C23 C16 C25 C26 . . . . -71.0(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H29 O5 . 0.84 1.98 2.7495(17) 151.7 ?
O6 H31 N2 3_546 0.84 1.95 2.7653(19) 162.4 ?
N1 H30 O5 . 0.88 2.28 2.8946(18) 126.6 ?
N4 H32 N3 3_646 0.88 2.10 2.925(2) 155.3 ?
C19 H20 O6 3_656 0.95 2.57 3.369(2) 141.8 ?
C24 H22 O2 3_646 0.99 2.49 3.329(2) 142.8 ?

