# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_24-013-[PTD_100K=RUPMOH]
_database_code_depnum_ccdc_archive 'CCDC 2495076'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Ireland
;
_audit_update_record             
;
2025-10-13 deposited with the CCDC.	2026-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            PTD
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N7 O2'
_chemical_formula_sum            'C15 H19 N7 O2'
_chemical_formula_weight         329.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

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

_cell_length_a                   19.9149(3)
_cell_length_b                   7.53694(11)
_cell_length_c                   21.0270(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3156.10(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    104(2)
_cell_measurement_reflns_used    6657
_cell_measurement_theta_min      4.189
_cell_measurement_theta_max      72.490

_exptl_crystal_description       Lathe
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.806
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      104(3)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa dual'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12559
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.205
_diffrn_reflns_theta_max         72.745
_diffrn_reflns_theta_full        72.745
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3070
_reflns_number_gt                2746
_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       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury program'
_computing_publication_material  'Standard preparation'
_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)+(0.0496P)²+0.7392P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00077(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3070
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044

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
O1 O 0.39203(5) 0.30530(13) 0.51225(5) 0.0304(2) Uani 1 1 d . . . . .
H1 H 0.3684(11) 0.286(3) 0.5478(10) 0.059(6) Uiso 1 1 d . . . . .
O2 O 0.97780(5) 0.75998(15) 0.47965(5) 0.0370(3) Uani 1 1 d . . . . .
H2 H 1.0215(10) 0.776(3) 0.4926(9) 0.051(5) Uiso 1 1 d . . . . .
C1 C 0.34561(6) 0.60864(17) 0.43639(6) 0.0269(3) Uani 1 1 d . . . . .
H1A H 0.314950 0.710947 0.431047 0.032 Uiso 1 1 calc R U . . .
H1B H 0.374129 0.631753 0.474053 0.032 Uiso 1 1 calc R U . . .
C2 C 0.30439(6) 0.44171(18) 0.44778(7) 0.0287(3) Uani 1 1 d . . . . .
H2A H 0.274523 0.460930 0.484786 0.034 Uiso 1 1 calc R U . . .
H2B H 0.275708 0.419249 0.410176 0.034 Uiso 1 1 calc R U . . .
C3 C 0.34778(7) 0.28009(18) 0.46000(7) 0.0297(3) Uani 1 1 d . . . . .
H3A H 0.318528 0.176649 0.468631 0.036 Uiso 1 1 calc R U . . .
H3B H 0.374423 0.253639 0.421398 0.036 Uiso 1 1 calc R U . . .
C4 C 0.87616(6) 0.75757(17) 0.37812(6) 0.0244(3) Uani 1 1 d . . . . .
H4A H 0.883512 0.863207 0.405221 0.029 Uiso 1 1 calc R U . . .
H4B H 0.899592 0.777677 0.337223 0.029 Uiso 1 1 calc R U . . .
C5 C 0.90609(6) 0.59570(17) 0.41063(6) 0.0253(3) Uani 1 1 d . . . . .
H5A H 0.879433 0.565968 0.448913 0.030 Uiso 1 1 calc R U . . .
H5B H 0.904599 0.492867 0.381365 0.030 Uiso 1 1 calc R U . . .
C6 C 0.97812(6) 0.63323(19) 0.42948(7) 0.0289(3) Uani 1 1 d . . . . .
H6A H 1.000176 0.522505 0.443794 0.035 Uiso 1 1 calc R U . . .
H6B H 1.003339 0.680333 0.392587 0.035 Uiso 1 1 calc R U . . .
N11 N 0.58767(5) 0.63570(14) 0.31510(5) 0.0223(2) Uani 1 1 d . . . . .
C12 C 0.53518(6) 0.57776(16) 0.28068(6) 0.0225(3) Uani 1 1 d . . . . .
C13 C 0.54123(6) 0.51479(17) 0.21859(6) 0.0251(3) Uani 1 1 d . . . . .
H13 H 0.503041 0.473704 0.195869 0.030 Uiso 1 1 calc R U . . .
C14 C 0.60432(7) 0.51366(17) 0.19087(6) 0.0268(3) Uani 1 1 d . . . . .
H14 H 0.609956 0.473617 0.148366 0.032 Uiso 1 1 calc R U . . .
C15 C 0.65891(6) 0.57126(17) 0.22561(6) 0.0251(3) Uani 1 1 d . . . . .
H15 H 0.702647 0.570988 0.207571 0.030 Uiso 1 1 calc R U . . .
C16 C 0.64855(6) 0.63001(16) 0.28788(6) 0.0219(3) Uani 1 1 d . . . . .
C21 C 0.46976(6) 0.57915(16) 0.31269(6) 0.0234(3) Uani 1 1 d . . . . .
C22 C 0.45584(6) 0.59654(16) 0.37635(6) 0.0236(3) Uani 1 1 d . . . . .
H22 H 0.486956 0.608468 0.410333 0.028 Uiso 1 1 calc R U . . .
N23 N 0.38831(5) 0.59296(14) 0.37998(5) 0.0242(2) Uani 1 1 d . . . . .
N24 N 0.36081(5) 0.57331(15) 0.32176(5) 0.0280(3) Uani 1 1 d . . . . .
N25 N 0.41048(5) 0.56457(15) 0.28056(5) 0.0271(3) Uani 1 1 d . . . . .
C31 C 0.70601(6) 0.68174(16) 0.32749(6) 0.0220(3) Uani 1 1 d . . . . .
C32 C 0.77339(6) 0.68330(16) 0.31271(6) 0.0231(3) Uani 1 1 d . . . . .
H32 H 0.793698 0.652963 0.273305 0.028 Uiso 1 1 calc R U . . .
N33 N 0.80405(5) 0.73702(13) 0.36614(5) 0.0223(2) Uani 1 1 d . . . . .
N34 N 0.75972(5) 0.76705(15) 0.41282(5) 0.0257(2) Uani 1 1 d . . . . .
N35 N 0.69973(5) 0.73338(14) 0.38936(5) 0.0245(2) Uani 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
O1 C3 1.4211(17) . ?
O1 H1 0.90(2) . ?
O2 C6 1.4233(16) . ?
O2 H2 0.92(2) . ?
C1 N23 1.4642(16) . ?
C1 C2 1.5213(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5155(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N33 1.4663(14) . ?
C4 C5 1.5201(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5149(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N11 C16 1.3414(15) . ?
N11 C12 1.3444(16) . ?
C12 C13 1.3944(18) . ?
C12 C21 1.4664(17) . ?
C13 C14 1.3851(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3799(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3975(18) . ?
C15 H15 0.9500 . ?
C16 C31 1.4680(17) . ?
C21 N25 1.3646(15) . ?
C21 C22 1.3734(18) . ?
C22 N23 1.3473(15) . ?
C22 H22 0.9500 . ?
N23 N24 1.3491(15) . ?
N24 N25 1.3167(16) . ?
C31 N35 1.3636(16) . ?
C31 C32 1.3775(16) . ?
C32 N33 1.3412(16) . ?
C32 H32 0.9500 . ?
N33 N34 1.3393(15) . ?
N34 N35 1.3171(14) . ?

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
C3 O1 H1 107.3(13) . . ?
C6 O2 H2 107.5(13) . . ?
N23 C1 C2 111.98(11) . . ?
N23 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N23 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 112.56(10) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 C2 112.16(11) . . ?
O1 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
O1 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N33 C4 C5 112.11(10) . . ?
N33 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N33 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 109.82(10) . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
O2 C6 C5 108.37(10) . . ?
O2 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
O2 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C16 N11 C12 117.57(11) . . ?
N11 C12 C13 123.19(11) . . ?
N11 C12 C21 116.19(11) . . ?
C13 C12 C21 120.60(11) . . ?
C14 C13 C12 118.32(11) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C15 C14 C13 119.34(12) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 118.64(11) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N11 C16 C15 122.91(11) . . ?
N11 C16 C31 117.00(11) . . ?
C15 C16 C31 120.04(11) . . ?
N25 C21 C22 108.40(11) . . ?
N25 C21 C12 122.74(12) . . ?
C22 C21 C12 128.86(11) . . ?
N23 C22 C21 104.75(11) . . ?
N23 C22 H22 127.6 . . ?
C21 C22 H22 127.6 . . ?
C22 N23 N24 110.87(10) . . ?
C22 N23 C1 128.60(11) . . ?
N24 N23 C1 120.54(10) . . ?
N25 N24 N23 107.31(10) . . ?
N24 N25 C21 108.67(11) . . ?
N35 C31 C32 107.58(10) . . ?
N35 C31 C16 123.07(10) . . ?
C32 C31 C16 129.32(11) . . ?
N33 C32 C31 104.90(10) . . ?
N33 C32 H32 127.6 . . ?
C31 C32 H32 127.6 . . ?
N34 N33 C32 111.39(10) . . ?
N34 N33 C4 120.12(10) . . ?
C32 N33 C4 128.44(11) . . ?
N35 N34 N33 106.91(10) . . ?
N34 N35 C31 109.21(10) . . ?

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
N23 C1 C2 C3 61.98(15) . . . . ?
C1 C2 C3 O1 56.81(15) . . . . ?
N33 C4 C5 C6 -172.70(10) . . . . ?
C4 C5 C6 O2 69.41(14) . . . . ?
C16 N11 C12 C13 -0.70(18) . . . . ?
C16 N11 C12 C21 177.66(10) . . . . ?
N11 C12 C13 C14 -0.68(19) . . . . ?
C21 C12 C13 C14 -178.97(11) . . . . ?
C12 C13 C14 C15 1.17(18) . . . . ?
C13 C14 C15 C16 -0.32(19) . . . . ?
C12 N11 C16 C15 1.62(18) . . . . ?
C12 N11 C16 C31 -175.79(11) . . . . ?
C14 C15 C16 N11 -1.13(19) . . . . ?
C14 C15 C16 C31 176.21(11) . . . . ?
N11 C12 C21 N25 164.32(11) . . . . ?
C13 C12 C21 N25 -17.27(18) . . . . ?
N11 C12 C21 C22 -14.73(18) . . . . ?
C13 C12 C21 C22 163.68(13) . . . . ?
N25 C21 C22 N23 -0.42(13) . . . . ?
C12 C21 C22 N23 178.74(12) . . . . ?
C21 C22 N23 N24 0.33(13) . . . . ?
C21 C22 N23 C1 -179.12(11) . . . . ?
C2 C1 N23 C22 -117.15(13) . . . . ?
C2 C1 N23 N24 63.44(14) . . . . ?
C22 N23 N24 N25 -0.12(14) . . . . ?
C1 N23 N24 N25 179.38(10) . . . . ?
N23 N24 N25 C21 -0.15(13) . . . . ?
C22 C21 N25 N24 0.36(14) . . . . ?
C12 C21 N25 N24 -178.86(11) . . . . ?
N11 C16 C31 N35 0.21(18) . . . . ?
C15 C16 C31 N35 -177.29(12) . . . . ?
N11 C16 C31 C32 177.86(12) . . . . ?
C15 C16 C31 C32 0.4(2) . . . . ?
N35 C31 C32 N33 -0.48(13) . . . . ?
C16 C31 C32 N33 -178.42(12) . . . . ?
C31 C32 N33 N34 0.50(14) . . . . ?
C31 C32 N33 C4 177.99(11) . . . . ?
C5 C4 N33 N34 81.06(14) . . . . ?
C5 C4 N33 C32 -96.23(15) . . . . ?
C32 N33 N34 N35 -0.32(14) . . . . ?
C4 N33 N34 N35 -178.05(10) . . . . ?
N33 N34 N35 C31 0.00(14) . . . . ?
C32 C31 N35 N34 0.31(14) . . . . ?
C16 C31 N35 N34 178.40(11) . . . . ?

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
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A    D-H        H...A      D...A       D-H...A   symm   publ
#   -    -    -    ---        -----      -----       -------   ----   ----
O1 H1 N35 0.90(2) 1.90(2) 2.7757(14) 165.8(19) 5_666 yes
O2 H2 O1 0.92(2) 1.78(2) 2.7031(13) 176.2(19) 8_765 yes
C1 H1B O2 0.99 2.42 3.3208(16) 150 4_466 yes
C22 H22 O2 0.95 2.52 3.2446(16) 133 4_466 yes
C32 H32 N24 0.95 2.48 3.4225(16) 173 6_656 yes
#   C32  H32  N25  0.95       2.67       3.4786(16)  143       6_656  yes


####################################################################### 
# 
# 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_24-011-[DEG_BTrzPhen]
_database_code_depnum_ccdc_archive 'CCDC 2495074'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Ireland
;
_audit_update_record             
;
2025-10-13 deposited with the CCDC.	2026-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            DEG_BTrzPhen
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N8 O4, H2 O'
_chemical_formula_sum            'C24 H28 N8 O5'
_chemical_formula_weight         508.54

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

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

_cell_length_a                   31.037(3)
_cell_length_b                   17.2042(16)
_cell_length_c                   4.3924(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2345.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4026
_cell_measurement_theta_min      2.843
_cell_measurement_theta_max      72.538

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.866
_shelx_estimated_absorpt_T_min   0.647
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100.2(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa dual'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            11231
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.847
_diffrn_reflns_theta_max         73.604
_diffrn_reflns_theta_full        73.605
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.677
_diffrn_reflns_point_group_measured_fraction_full 0.677
_reflns_number_total             3209
_reflns_number_gt                2804
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.222
_reflns_Friedel_fraction_max     0.284
_reflns_Friedel_fraction_full    0.285

_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       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury program'
_computing_publication_material  'Standard preparation'
_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)+(0.0143P)²+6.3495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3209
_refine_ls_number_parameters     347
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.073


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
O1 O 0.18100(11) 0.2590(2) 0.0931(11) 0.0248(10) Uani 1 1 d . . . . .
O2 O 0.09011(13) 0.2487(3) 0.2805(14) 0.0405(13) Uani 1 1 d . . . . .
H2 H 0.071(3) 0.221(5) 0.35(2) 0.061 Uiso 1 1 d . U . . .
O3 O 0.38318(11) 0.4832(2) 0.2678(12) 0.0266(10) Uani 1 1 d . . . . .
O4 O 0.31994(13) 0.3554(2) 0.2223(14) 0.0349(12) Uani 1 1 d . . . . .
H4 H 0.334(2) 0.344(5) 0.04(2) 0.052 Uiso 1 1 d . U . . .
C1 C 0.23963(17) 0.2219(3) -0.2496(17) 0.0256(14) Uani 1 1 d . . . . .
H1A H 0.219259 0.199031 -0.398258 0.031 Uiso 1 1 calc R U . . .
H1B H 0.263940 0.244534 -0.365343 0.031 Uiso 1 1 calc R U . . .
C2 C 0.21692(17) 0.2862(3) -0.0764(17) 0.0255(14) Uani 1 1 d . . . . .
H2A H 0.237682 0.311114 0.064319 0.031 Uiso 1 1 calc R U . . .
H2B H 0.207048 0.326263 -0.222554 0.031 Uiso 1 1 calc R U . . .
C3 C 0.14461(18) 0.2439(4) -0.1002(18) 0.0316(16) Uani 1 1 d . . . . .
H3A H 0.153937 0.213757 -0.280537 0.038 Uiso 1 1 calc R U . . .
H3B H 0.132170 0.293630 -0.171827 0.038 Uiso 1 1 calc R U . . .
C4 C 0.11141(18) 0.1992(4) 0.072(2) 0.0342(17) Uani 1 1 d . . . . .
H4A H 0.090210 0.176705 -0.071504 0.041 Uiso 1 1 calc R U . . .
H4B H 0.125335 0.155918 0.183593 0.041 Uiso 1 1 calc R U . . .
C5 C 0.44277(17) 0.4494(3) -0.0665(16) 0.0240(14) Uani 1 1 d . . . . .
H5A H 0.421787 0.425912 -0.209167 0.029 Uiso 1 1 calc R U . . .
H5B H 0.466323 0.472715 -0.187963 0.029 Uiso 1 1 calc R U . . .
C6 C 0.42065(18) 0.5124(3) 0.1190(17) 0.0255(14) Uani 1 1 d . . . . .
H6A H 0.440978 0.532862 0.273170 0.031 Uiso 1 1 calc R U . . .
H6B H 0.412405 0.555864 -0.016863 0.031 Uiso 1 1 calc R U . . .
C7 C 0.34600(17) 0.4854(3) 0.0791(19) 0.0308(16) Uani 1 1 d . . . . .
H7A H 0.353461 0.465899 -0.126208 0.037 Uiso 1 1 calc R U . . .
H7B H 0.336073 0.539852 0.058241 0.037 Uiso 1 1 calc R U . . .
C8 C 0.31056(18) 0.4372(3) 0.2089(18) 0.0282(15) Uani 1 1 d . . . . .
H8A H 0.304168 0.455889 0.417273 0.034 Uiso 1 1 calc R U . . .
H8B H 0.284327 0.444936 0.084323 0.034 Uiso 1 1 calc R U . . .
C11 C 0.38712(16) 0.0734(3) 0.7183(15) 0.0173(12) Uani 1 1 d . . . . .
C12 C 0.38445(17) -0.0005(3) 0.8588(15) 0.0203(13) Uani 1 1 d . . . . .
C13 C 0.41758(18) -0.0269(3) 1.0578(18) 0.0280(15) Uani 1 1 d . . . . .
H13 H 0.415059 -0.076425 1.152091 0.034 Uiso 1 1 calc R U . . .
C14 C 0.45267(17) 0.0177(3) 1.1143(16) 0.0232(13) Uani 1 1 d . . . . .
H14 H 0.473837 0.000532 1.255170 0.028 Uiso 1 1 calc R U . . .
C15 C 0.45797(17) 0.0910(3) 0.9618(15) 0.0198(12) Uani 1 1 d . . . . .
C16 C 0.42574(16) 0.1194(3) 0.7747(16) 0.0206(13) Uani 1 1 d . . . . .
N21 N 0.35671(13) 0.1018(2) 0.5378(12) 0.0169(10) Uani 1 1 d . . . . .
C22 C 0.32288(17) 0.0576(3) 0.4701(16) 0.0222(14) Uani 1 1 d . . . . .
C23 C 0.31747(17) -0.0176(3) 0.5938(16) 0.0248(14) Uani 1 1 d . . . . .
H23 H 0.292849 -0.047791 0.543233 0.030 Uiso 1 1 calc R U . . .
C24 C 0.34823(17) -0.0467(3) 0.7881(17) 0.0248(14) Uani 1 1 d . . . . .
H24 H 0.345153 -0.097078 0.873513 0.030 Uiso 1 1 calc R U . . .
N25 N 0.42958(13) 0.1874(2) 0.6189(14) 0.0200(11) Uani 1 1 d . . . . .
C26 C 0.46692(16) 0.2260(3) 0.6388(16) 0.0215(13) Uani 1 1 d . . . . .
C27 C 0.50107(16) 0.2011(3) 0.8239(16) 0.0214(14) Uani 1 1 d . . . . .
H27 H 0.527091 0.230073 0.832252 0.026 Uiso 1 1 calc R U . . .
C28 C 0.49658(18) 0.1351(3) 0.9915(17) 0.0246(14) Uani 1 1 d . . . . .
H28 H 0.518795 0.118660 1.125680 0.030 Uiso 1 1 calc R U . . .
C31 C 0.29076(16) 0.0901(3) 0.2697(14) 0.0166(11) Uani 1 1 d . . . . .
C32 C 0.29268(16) 0.1582(3) 0.1036(15) 0.0203(13) Uani 1 1 d . . . . .
H32 H 0.315357 0.195253 0.102651 0.024 Uiso 1 1 calc R U . . .
N33 N 0.25579(13) 0.1611(3) -0.0566(12) 0.0189(10) Uani 1 1 d . . . . .
N34 N 0.23126(15) 0.0974(3) 0.0040(14) 0.0256(12) Uani 1 1 d . . . . .
N35 N 0.25242(14) 0.0540(3) 0.1977(13) 0.0230(11) Uani 1 1 d . . . . .
C41 C 0.47057(16) 0.2949(3) 0.4481(16) 0.0217(13) Uani 1 1 d . . . . .
C42 C 0.43997(16) 0.3298(3) 0.2625(16) 0.0212(13) Uani 1 1 d . . . . .
H42 H 0.410808 0.314551 0.234814 0.025 Uiso 1 1 calc R U . . .
N43 N 0.46034(13) 0.3891(2) 0.1316(13) 0.0215(11) Uani 1 1 d . . . . .
N44 N 0.50220(14) 0.3923(2) 0.2169(15) 0.0255(12) Uani 1 1 d . . . . .
N45 N 0.50839(14) 0.3350(3) 0.4108(14) 0.0247(12) Uani 1 1 d . . . . .
O1W O 0.35514(15) 0.2919(3) 0.7222(14) 0.0407(13) Uani 1 1 d D . . . .
H1W H 0.340(2) 0.299(4) 0.554(10) 0.061 Uiso 1 1 d D U . . .
H2W H 0.370(2) 0.250(3) 0.675(17) 0.061 Uiso 1 1 d D U . . .


_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 1.420(7) . ?
O1 C3 1.437(7) . ?
O2 C4 1.415(9) . ?
O2 H2 0.83(8) . ?
O3 C7 1.421(7) . ?
O3 C6 1.425(7) . ?
O4 C8 1.438(6) . ?
O4 H4 0.93(9) . ?
C1 N33 1.437(7) . ?
C1 C2 1.518(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.492(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N43 1.459(7) . ?
C5 C6 1.520(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.491(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C11 N21 1.326(7) . ?
C11 C12 1.416(8) . ?
C11 C16 1.457(7) . ?
C12 C24 1.411(8) . ?
C12 C13 1.424(9) . ?
C13 C14 1.356(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.437(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(8) . ?
C15 C28 1.424(8) . ?
C16 N25 1.360(7) . ?
N21 C22 1.330(7) . ?
C22 C23 1.414(8) . ?
C22 C31 1.443(8) . ?
C23 C24 1.374(9) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N25 C26 1.339(6) . ?
C26 C27 1.403(8) . ?
C26 C41 1.457(8) . ?
C27 C28 1.360(8) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C31 N35 1.379(6) . ?
C31 C32 1.381(8) . ?
C32 N33 1.345(7) . ?
C32 H32 0.9500 . ?
N33 N34 1.360(6) . ?
N34 N35 1.308(7) . ?
C41 N45 1.371(7) . ?
C41 C42 1.388(8) . ?
C42 N43 1.332(7) . ?
C42 H42 0.9500 . ?
N43 N44 1.353(6) . ?
N44 N45 1.317(7) . ?
O1W H1W 0.884(12) . ?
O1W H2W 0.882(12) . ?

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 C3 111.5(5) . . ?
C4 O2 H2 103(6) . . ?
C7 O3 C6 112.7(5) . . ?
C8 O4 H4 106(5) . . ?
N33 C1 C2 113.4(6) . . ?
N33 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N33 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
O1 C2 C1 112.7(4) . . ?
O1 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
O1 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 C4 109.7(6) . . ?
O1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
O1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O2 C4 C3 109.9(5) . . ?
O2 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
O2 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N43 C5 C6 110.9(6) . . ?
N43 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N43 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
O3 C6 C5 111.3(4) . . ?
O3 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
O3 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O3 C7 C8 111.2(6) . . ?
O3 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
O3 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O4 C8 C7 114.2(5) . . ?
O4 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
O4 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N21 C11 C12 123.4(5) . . ?
N21 C11 C16 119.2(5) . . ?
C12 C11 C16 117.5(5) . . ?
C24 C12 C11 117.1(5) . . ?
C24 C12 C13 122.0(5) . . ?
C11 C12 C13 120.8(5) . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.3(6) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C28 118.4(5) . . ?
C16 C15 C14 120.2(5) . . ?
C28 C15 C14 121.4(5) . . ?
N25 C16 C15 122.6(5) . . ?
N25 C16 C11 116.9(5) . . ?
C15 C16 C11 120.3(5) . . ?
C11 N21 C22 119.0(5) . . ?
N21 C22 C23 122.1(5) . . ?
N21 C22 C31 117.4(5) . . ?
C23 C22 C31 120.5(5) . . ?
C24 C23 C22 119.3(5) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C12 119.0(5) . . ?
C23 C24 H24 120.5 . . ?
C12 C24 H24 120.5 . . ?
C26 N25 C16 118.0(5) . . ?
N25 C26 C27 122.7(5) . . ?
N25 C26 C41 115.7(5) . . ?
C27 C26 C41 121.6(5) . . ?
C28 C27 C26 119.4(5) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C27 C28 C15 118.7(6) . . ?
C27 C28 H28 120.6 . . ?
C15 C28 H28 120.6 . . ?
N35 C31 C32 107.3(5) . . ?
N35 C31 C22 124.2(5) . . ?
C32 C31 C22 128.4(5) . . ?
N33 C32 C31 105.7(5) . . ?
N33 C32 H32 127.1 . . ?
C31 C32 H32 127.1 . . ?
C32 N33 N34 110.1(5) . . ?
C32 N33 C1 129.3(5) . . ?
N34 N33 C1 120.4(4) . . ?
N35 N34 N33 107.8(4) . . ?
N34 N35 C31 109.0(4) . . ?
N45 C41 C42 107.4(5) . . ?
N45 C41 C26 123.0(5) . . ?
C42 C41 C26 129.5(5) . . ?
N43 C42 C41 105.0(5) . . ?
N43 C42 H42 127.5 . . ?
C41 C42 H42 127.5 . . ?
C42 N43 N44 111.5(5) . . ?
C42 N43 C5 128.7(5) . . ?
N44 N43 C5 119.7(4) . . ?
N45 N44 N43 106.8(4) . . ?
N44 N45 C41 109.2(5) . . ?
H1W O1W H2W 101(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
C3 O1 C2 C1 -76.1(6) . . . . ?
N33 C1 C2 O1 -59.5(7) . . . . ?
C2 O1 C3 C4 167.3(5) . . . . ?
O1 C3 C4 O2 74.4(7) . . . . ?
C7 O3 C6 C5 -85.6(6) . . . . ?
N43 C5 C6 O3 -66.4(6) . . . . ?
C6 O3 C7 C8 165.8(5) . . . . ?
O3 C7 C8 O4 -64.7(8) . . . . ?
N21 C11 C12 C24 3.1(9) . . . . ?
C16 C11 C12 C24 -176.1(6) . . . . ?
N21 C11 C12 C13 -178.1(6) . . . . ?
C16 C11 C12 C13 2.7(8) . . . . ?
C24 C12 C13 C14 177.9(6) . . . . ?
C11 C12 C13 C14 -0.8(9) . . . . ?
C12 C13 C14 C15 -3.1(9) . . . . ?
C13 C14 C15 C16 5.1(9) . . . . ?
C13 C14 C15 C28 -173.1(6) . . . . ?
C28 C15 C16 N25 0.0(9) . . . . ?
C14 C15 C16 N25 -178.2(6) . . . . ?
C28 C15 C16 C11 175.1(6) . . . . ?
C14 C15 C16 C11 -3.1(9) . . . . ?
N21 C11 C16 N25 -4.5(9) . . . . ?
C12 C11 C16 N25 174.7(5) . . . . ?
N21 C11 C16 C15 -179.9(6) . . . . ?
C12 C11 C16 C15 -0.7(9) . . . . ?
C12 C11 N21 C22 -3.7(9) . . . . ?
C16 C11 N21 C22 175.4(5) . . . . ?
C11 N21 C22 C23 2.5(9) . . . . ?
C11 N21 C22 C31 -179.2(5) . . . . ?
N21 C22 C23 C24 -0.6(9) . . . . ?
C31 C22 C23 C24 -178.9(6) . . . . ?
C22 C23 C24 C12 0.0(9) . . . . ?
C11 C12 C24 C23 -1.1(9) . . . . ?
C13 C12 C24 C23 -179.9(6) . . . . ?
C15 C16 N25 C26 3.1(9) . . . . ?
C11 C16 N25 C26 -172.2(5) . . . . ?
C16 N25 C26 C27 -3.2(9) . . . . ?
C16 N25 C26 C41 175.1(5) . . . . ?
N25 C26 C27 C28 0.1(9) . . . . ?
C41 C26 C27 C28 -178.1(6) . . . . ?
C26 C27 C28 C15 3.1(9) . . . . ?
C16 C15 C28 C27 -3.1(9) . . . . ?
C14 C15 C28 C27 175.1(6) . . . . ?
N21 C22 C31 N35 -174.7(5) . . . . ?
C23 C22 C31 N35 3.6(9) . . . . ?
N21 C22 C31 C32 9.3(9) . . . . ?
C23 C22 C31 C32 -172.4(6) . . . . ?
N35 C31 C32 N33 0.8(6) . . . . ?
C22 C31 C32 N33 177.3(6) . . . . ?
C31 C32 N33 N34 -0.1(6) . . . . ?
C31 C32 N33 C1 175.0(6) . . . . ?
C2 C1 N33 C32 -82.6(7) . . . . ?
C2 C1 N33 N34 92.1(6) . . . . ?
C32 N33 N34 N35 -0.7(7) . . . . ?
C1 N33 N34 N35 -176.3(5) . . . . ?
N33 N34 N35 C31 1.2(7) . . . . ?
C32 C31 N35 N34 -1.3(7) . . . . ?
C22 C31 N35 N34 -178.0(5) . . . . ?
N25 C26 C41 N45 -171.1(6) . . . . ?
C27 C26 C41 N45 7.2(9) . . . . ?
N25 C26 C41 C42 4.7(10) . . . . ?
C27 C26 C41 C42 -177.0(6) . . . . ?
N45 C41 C42 N43 -1.5(7) . . . . ?
C26 C41 C42 N43 -177.9(6) . . . . ?
C41 C42 N43 N44 1.8(7) . . . . ?
C41 C42 N43 C5 -174.5(6) . . . . ?
C6 C5 N43 C42 80.4(7) . . . . ?
C6 C5 N43 N44 -95.7(6) . . . . ?
C42 N43 N44 N45 -1.4(7) . . . . ?
C5 N43 N44 N45 175.3(5) . . . . ?
N43 N44 N45 C41 0.4(7) . . . . ?
C42 C41 N45 N44 0.7(7) . . . . ?
C26 C41 N45 N44 177.4(6) . . . . ?

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
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A    D-H        H...A      D...A       D-H...A   symm   publ
#   -    -    -    ---        -----      -----       -------   ----   ----
#   C8   H8A  N34  0.99       2.70       3.311(7)    120.3     3      no
#   O1W  H2W  N21  0.882(12)  2.64(5)    3.368(6)    140(6)    .      no
O2 H2 N45 0.83(8) 2.18(8) 2.973(6) 161(9) 4_455 yes
O4 H4 O1W 0.93(9) 1.79(9) 2.686(8) 162(7) 1_554 yes
C5 H5B N44 0.99 2.55 3.353(7) 137.7 2_664 yes
O1W H1W O4 0.884(12) 1.86(4) 2.685(8) 155(7) . yes
O1W H2W N25 0.882(12) 2.16(3) 2.962(6) 151(6) . yes

####################################################################### 
# 
# 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_24-012_[HE-PTD_3]
_database_code_depnum_ccdc_archive 'CCDC 2495075'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Ireland
;
_audit_update_record             
;
2025-10-13 deposited with the CCDC.	2026-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            HE-PTD
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N7 O2'
_chemical_formula_sum            'C13 H15 N7 O2'
_chemical_formula_weight         301.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   8.42287(15)
_cell_length_b                   7.05057(12)
_cell_length_c                   23.7774(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.2579(15)
_cell_angle_gamma                90
_cell_volume                     1406.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5088
_cell_measurement_theta_min      3.728
_cell_measurement_theta_max      68.117

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.950
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.450
_exptl_absorpt_coefficient_mu    0.853
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100.2(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa dual'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            6592
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.734
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_full        68.228
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2551
_reflns_number_gt                2374
_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       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury program'
_computing_publication_material  'Standard preparation'
_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)+(0.0751P)²+0.5136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0135(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2551
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.067

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
O1 O 0.92852(13) 0.29139(16) 0.64667(5) 0.0222(3) Uani 1 1 d . . . . .
H1 H 0.859(3) 0.373(3) 0.6438(9) 0.038(6) Uiso 1 1 d . . . . .
O2 O 0.85589(13) 0.20584(16) 0.34895(5) 0.0254(3) Uani 1 1 d . . . . .
H2 H 0.781(3) 0.118(4) 0.3511(10) 0.057(7) Uiso 1 1 d . . . . .
C1 C 0.81548(17) -0.0047(2) 0.67675(6) 0.0180(3) Uani 1 1 d . . . . .
H1A H 0.876662 -0.077028 0.650316 0.022 Uiso 1 1 calc R U . . .
H1B H 0.806875 -0.084130 0.710672 0.022 Uiso 1 1 calc R U . . .
C2 C 0.90478(18) 0.1757(2) 0.69383(6) 0.0203(3) Uani 1 1 d . . . . .
H2A H 0.843935 0.247830 0.720422 0.024 Uiso 1 1 calc R U . . .
H2B H 1.009573 0.142645 0.713692 0.024 Uiso 1 1 calc R U . . .
C3 C 0.72715(17) 0.5081(2) 0.32805(6) 0.0195(3) Uani 1 1 d . . . . .
H3A H 0.805543 0.568832 0.355977 0.023 Uiso 1 1 calc R U . . .
H3B H 0.701984 0.599027 0.296787 0.023 Uiso 1 1 calc R U . . .
C4 C 0.80058(18) 0.3316(2) 0.30510(6) 0.0209(4) Uani 1 1 d . . . . .
H4A H 0.720204 0.266215 0.278959 0.025 Uiso 1 1 calc R U . . .
H4B H 0.890725 0.368351 0.283450 0.025 Uiso 1 1 calc R U . . .
N11 N 0.41356(14) 0.24554(15) 0.50148(5) 0.0135(3) Uani 1 1 d . . . . .
C12 C 0.34206(16) 0.17827(19) 0.54558(6) 0.0140(3) Uani 1 1 d . . . . .
C13 C 0.17636(17) 0.1751(2) 0.54711(6) 0.0183(3) Uani 1 1 d . . . . .
H13 H 0.129464 0.126042 0.578913 0.022 Uiso 1 1 calc R U . . .
C14 C 0.08294(17) 0.2456(2) 0.50096(6) 0.0207(3) Uani 1 1 d . . . . .
H14 H -0.029894 0.246009 0.500788 0.025 Uiso 1 1 calc R U . . .
C15 C 0.15423(17) 0.3156(2) 0.45496(6) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.091784 0.364039 0.422859 0.023 Uiso 1 1 calc R U . . .
C16 C 0.32017(16) 0.31279(18) 0.45712(6) 0.0142(3) Uani 1 1 d . . . . .
C21 C 0.45072(16) 0.11129(18) 0.59322(5) 0.0139(3) Uani 1 1 d . . . . .
C22 C 0.61457(16) 0.10321(19) 0.59780(5) 0.0145(3) Uani 1 1 d . . . . .
H22 H 0.683824 0.139003 0.570271 0.017 Uiso 1 1 calc R U . . .
N23 N 0.65524(14) 0.03366(16) 0.64971(5) 0.0145(3) Uani 1 1 d . . . . .
N24 N 0.52517(14) -0.00097(16) 0.67721(5) 0.0165(3) Uani 1 1 d . . . . .
N25 N 0.40028(14) 0.04671(17) 0.64262(5) 0.0162(3) Uani 1 1 d . . . . .
C31 C 0.40572(16) 0.38235(18) 0.41022(6) 0.0138(3) Uani 1 1 d . . . . .
C32 C 0.56726(17) 0.39169(19) 0.40613(5) 0.0149(3) Uani 1 1 d . . . . .
H32 H 0.650402 0.353742 0.433522 0.018 Uiso 1 1 calc R U . . .
N33 N 0.58160(14) 0.46621(16) 0.35493(5) 0.0151(3) Uani 1 1 d . . . . .
N34 N 0.43805(14) 0.50238(17) 0.32730(5) 0.0170(3) Uani 1 1 d . . . . .
N35 N 0.33040(14) 0.45126(17) 0.36117(5) 0.0160(3) Uani 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
O1 C2 1.4154(18) . ?
O1 H1 0.82(2) . ?
O2 C4 1.4148(18) . ?
O2 H2 0.89(3) . ?
C1 N23 1.4660(18) . ?
C1 C2 1.514(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N33 1.4637(17) . ?
C3 C4 1.513(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N11 C12 1.3428(18) . ?
N11 C16 1.3431(18) . ?
C12 C13 1.400(2) . ?
C12 C21 1.4675(19) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H15 0.9500 . ?
C16 C31 1.4665(19) . ?
C21 N25 1.3634(17) . ?
C21 C22 1.3755(19) . ?
C22 N23 1.3430(18) . ?
C22 H22 0.9500 . ?
N23 N24 1.3486(16) . ?
N24 N25 1.3181(17) . ?
C31 N35 1.3651(18) . ?
C31 C32 1.3745(19) . ?
C32 N33 1.3415(18) . ?
C32 H32 0.9500 . ?
N33 N34 1.3464(17) . ?
N34 N35 1.3169(16) . ?

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 108.6(15) . . ?
C4 O2 H2 106.9(15) . . ?
N23 C1 C2 112.17(12) . . ?
N23 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N23 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
O1 C2 C1 111.98(12) . . ?
O1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
O1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N33 C3 C4 112.22(12) . . ?
N33 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N33 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O2 C4 C3 111.55(12) . . ?
O2 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
O2 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C12 N11 C16 117.75(12) . . ?
N11 C12 C13 123.06(13) . . ?
N11 C12 C21 115.07(12) . . ?
C13 C12 C21 121.86(12) . . ?
C14 C13 C12 118.04(13) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C15 119.87(14) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 118.12(13) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
N11 C16 C15 123.16(13) . . ?
N11 C16 C31 114.96(12) . . ?
C15 C16 C31 121.88(13) . . ?
N25 C21 C22 107.90(12) . . ?
N25 C21 C12 123.42(12) . . ?
C22 C21 C12 128.67(12) . . ?
N23 C22 C21 104.93(12) . . ?
N23 C22 H22 127.5 . . ?
C21 C22 H22 127.5 . . ?
C22 N23 N24 111.19(11) . . ?
C22 N23 C1 128.13(12) . . ?
N24 N23 C1 120.68(11) . . ?
N25 N24 N23 106.78(11) . . ?
N24 N25 C21 109.20(11) . . ?
N35 C31 C32 107.94(12) . . ?
N35 C31 C16 123.13(12) . . ?
C32 C31 C16 128.93(13) . . ?
N33 C32 C31 104.77(12) . . ?
N33 C32 H32 127.6 . . ?
C31 C32 H32 127.6 . . ?
C32 N33 N34 111.44(11) . . ?
C32 N33 C3 128.60(12) . . ?
N34 N33 C3 119.96(11) . . ?
N35 N34 N33 106.72(10) . . ?
N34 N35 C31 109.13(11) . . ?

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
N23 C1 C2 O1 -61.96(16) . . . . ?
N33 C3 C4 O2 -65.67(16) . . . . ?
C16 N11 C12 C13 0.13(19) . . . . ?
C16 N11 C12 C21 -178.56(11) . . . . ?
N11 C12 C13 C14 -0.3(2) . . . . ?
C21 C12 C13 C14 178.33(13) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C12 N11 C16 C15 -0.04(19) . . . . ?
C12 N11 C16 C31 -179.45(11) . . . . ?
C14 C15 C16 N11 0.1(2) . . . . ?
C14 C15 C16 C31 179.46(13) . . . . ?
N11 C12 C21 N25 176.79(12) . . . . ?
C13 C12 C21 N25 -1.9(2) . . . . ?
N11 C12 C21 C22 -2.2(2) . . . . ?
C13 C12 C21 C22 179.12(13) . . . . ?
N25 C21 C22 N23 0.15(15) . . . . ?
C12 C21 C22 N23 179.25(13) . . . . ?
C21 C22 N23 N24 -0.11(15) . . . . ?
C21 C22 N23 C1 179.85(13) . . . . ?
C2 C1 N23 C22 72.86(18) . . . . ?
C2 C1 N23 N24 -107.18(14) . . . . ?
C22 N23 N24 N25 0.03(15) . . . . ?
C1 N23 N24 N25 -179.94(11) . . . . ?
N23 N24 N25 C21 0.07(14) . . . . ?
C22 C21 N25 N24 -0.14(15) . . . . ?
C12 C21 N25 N24 -179.30(12) . . . . ?
N11 C16 C31 N35 178.32(12) . . . . ?
C15 C16 C31 N35 -1.1(2) . . . . ?
N11 C16 C31 C32 -1.6(2) . . . . ?
C15 C16 C31 C32 179.01(13) . . . . ?
N35 C31 C32 N33 0.17(14) . . . . ?
C16 C31 C32 N33 -179.93(13) . . . . ?
C31 C32 N33 N34 -0.25(15) . . . . ?
C31 C32 N33 C3 -179.94(13) . . . . ?
C4 C3 N33 C32 77.48(18) . . . . ?
C4 C3 N33 N34 -102.19(15) . . . . ?
C32 N33 N34 N35 0.23(15) . . . . ?
C3 N33 N34 N35 179.95(11) . . . . ?
N33 N34 N35 C31 -0.11(14) . . . . ?
C32 C31 N35 N34 -0.04(15) . . . . ?
C16 C31 N35 N34 -179.95(11) . . . . ?

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
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A    D-H        H...A      D...A       D-H...A   symm   publ
#   -    -    -    ---        -----      -----       -------   ----   ----
O1 H1 N35 0.82(2) 2.02(2) 2.8300(16) 173(2) 3_666 yes
O2 H2 N25 0.89(3) 1.94(3) 2.8188(16) 173(2) 3_656 yes
C1 H1A O2 0.99 2.43 3.2182(18) 137 3_756 yes
C3 H3A O1 0.99 2.45 3.2330(18) 135 3_766 yes


