#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:25:43 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299154 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/33/1573397.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1573397
loop_
_publ_author_name
'Maessen, Stefan J. D.'
'Lekanne Deprez, Siebe'
'Vermeeren, Pascal'
'van den Bersselaar, Bart W. L.'
'Lutz, Martin'
'Heuts, Johan P. A.'
'Fonseca Guerra, Célia'
'Palmans, Anja R. A.'
_publ_section_title
;
 Structure-property relationships to direct the dynamic properties of
 acylsemicarbazide-based materials.
;
_journal_issue                   3
_journal_name_full               'Polymer chemistry'
_journal_page_first              290
_journal_page_last               300
_journal_paper_doi               10.1039/d4py01296h
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C15 H13 N3 O3'
_chemical_formula_sum            'C15 H13 N3 O3'
_chemical_formula_weight         283.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-08-13 deposited with the CCDC.	2024-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.644(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7633(3)
_cell_length_b                   27.5437(7)
_cell_length_c                   10.4855(3)
_cell_measurement_reflns_used    33241
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      1.47
_cell_volume                     2787.70(14)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex3
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            53558
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.479
_diffrn_source                   'sdealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_type   multi-scan
_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_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0506P)²+0.8158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5233
_reflns_number_total             6410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4py01296h2.cif
_cod_data_source_block           l1349a
_cod_depositor_comments
'Adding full bibliography for 1573396--1573397.cif.'
_cod_original_cell_volume        2787.70(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1573397
_shelx_shelxl_version_number     2019/3
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O11 O 0.82849(9) 0.48572(3) 0.50741(9) 0.0333(2) Uani 1 1 d . . . . .
O21 O 0.73213(9) 0.57096(3) 0.18892(8) 0.0275(2) Uani 1 1 d . . . . .
O31 O 0.88087(11) 0.65896(4) 0.40232(11) 0.0436(3) Uani 1 1 d . . . . .
N11 N 0.68303(11) 0.51445(4) 0.33393(10) 0.0240(2) Uani 1 1 d . . . . .
H11N H 0.6036(17) 0.5115(5) 0.2782(15) 0.034(4) Uiso 1 1 d . . . . .
N21 N 0.88553(11) 0.56060(4) 0.37096(11) 0.0258(2) Uani 1 1 d . . . . .
H21N H 0.9112(18) 0.5437(6) 0.4391(17) 0.043(5) Uiso 1 1 d . . . . .
N31 N 0.97874(11) 0.59242(4) 0.32786(11) 0.0266(2) Uani 1 1 d . . . . .
H31N H 1.0373(17) 0.5789(6) 0.2822(16) 0.036(4) Uiso 1 1 d . . . . .
C11 C 0.60929(13) 0.44704(4) 0.46134(12) 0.0247(3) Uani 1 1 d . . . . .
C21 C 0.48537(15) 0.43946(5) 0.38028(13) 0.0354(3) Uani 1 1 d . . . . .
H21 H 0.463453 0.458266 0.303991 0.042 Uiso 1 1 calc R U . . .
C31 C 0.39318(15) 0.40438(6) 0.41050(15) 0.0408(4) Uani 1 1 d . . . . .
H31 H 0.308100 0.399529 0.354853 0.049 Uiso 1 1 calc R U . . .
C41 C 0.42367(15) 0.37660(5) 0.52003(15) 0.0363(3) Uani 1 1 d . . . . .
H41 H 0.361453 0.351981 0.538630 0.044 Uiso 1 1 calc R U . . .
C51 C 0.54541(17) 0.38476(6) 0.60278(17) 0.0481(4) Uani 1 1 d . . . . .
H51 H 0.566184 0.366141 0.679527 0.058 Uiso 1 1 calc R U . . .
C61 C 0.63738(15) 0.42002(6) 0.57420(15) 0.0423(4) Uani 1 1 d . . . . .
H61 H 0.720288 0.425783 0.632226 0.051 Uiso 1 1 calc R U . . .
C71 C 0.71604(12) 0.48358(4) 0.43784(11) 0.0241(2) Uani 1 1 d . . . . .
C81 C 0.76747(12) 0.55023(4) 0.29324(11) 0.0223(2) Uani 1 1 d . . . . .
C91 C 0.96563(13) 0.64103(5) 0.34262(13) 0.0272(3) Uani 1 1 d . . . . .
C101 C 1.06639(13) 0.67102(4) 0.28145(12) 0.0262(3) Uani 1 1 d . . . . .
C111 C 1.11607(14) 0.65690(5) 0.16964(13) 0.0305(3) Uani 1 1 d . . . . .
H111 H 1.089433 0.626499 0.130869 0.037 Uiso 1 1 calc R U . . .
C121 C 1.20449(16) 0.68719(5) 0.11466(14) 0.0367(3) Uani 1 1 d . . . . .
H121 H 1.236719 0.677747 0.037233 0.044 Uiso 1 1 calc R U . . .
C131 C 1.24603(16) 0.73111(5) 0.17205(15) 0.0392(3) Uani 1 1 d . . . . .
H131 H 1.307786 0.751506 0.134810 0.047 Uiso 1 1 calc R U . . .
C141 C 1.19750(16) 0.74524(5) 0.28372(16) 0.0413(4) Uani 1 1 d . . . . .
H141 H 1.226469 0.775285 0.323404 0.050 Uiso 1 1 calc R U . . .
C151 C 1.10661(15) 0.71566(5) 0.33791(15) 0.0352(3) Uani 1 1 d . . . . .
H151 H 1.071766 0.725812 0.413468 0.042 Uiso 1 1 calc R U . . .
O12 O 0.32968(11) 0.61910(4) -0.13126(11) 0.0452(3) Uani 1 1 d . . . . .
O22 O 0.44236(9) 0.51169(3) 0.13470(9) 0.0306(2) Uani 1 1 d . . . . .
O32 O 0.12457(10) 0.53283(3) 0.17307(9) 0.0322(2) Uani 1 1 d . . . . .
N12 N 0.46980(12) 0.58337(4) 0.03561(11) 0.0290(2) Uani 1 1 d . . . . .
H12N H 0.5534(18) 0.5838(6) 0.0870(16) 0.038(4) Uiso 1 1 d . . . . .
N22 N 0.27152(12) 0.53583(4) -0.02319(11) 0.0291(2) Uani 1 1 d . . . . .
H22N H 0.2342(18) 0.5584(6) -0.0805(17) 0.043(4) Uiso 1 1 d . . . . .
N32 N 0.19231(11) 0.49603(4) 0.00120(10) 0.0271(2) Uani 1 1 d . . . . .
H32N H 0.2099(18) 0.4689(6) -0.0414(17) 0.046(5) Uiso 1 1 d . . . . .
C12 C 0.53538(15) 0.66128(5) -0.04559(16) 0.0384(3) Uani 1 1 d . . . . .
C22 C 0.63090(16) 0.67199(5) 0.06321(17) 0.0414(4) Uani 1 1 d . . . . .
H22 H 0.636387 0.652042 0.137713 0.050 Uiso 1 1 calc R U . . .
C32 C 0.71870(19) 0.71204(6) 0.0630(2) 0.0560(5) Uani 1 1 d . . . . .
H32 H 0.784811 0.719100 0.136749 0.067 Uiso 1 1 calc R U . . .
C42 C 0.7089(2) 0.74128(6) -0.0449(3) 0.0735(7) Uani 1 1 d . . . . .
H42 H 0.768110 0.768659 -0.044984 0.088 Uiso 1 1 calc R U . . .
C52 C 0.6143(2) 0.73105(8) -0.1519(3) 0.0798(8) Uani 1 1 d . . . . .
H52 H 0.607943 0.751586 -0.225377 0.096 Uiso 1 1 calc R U . . .
C62 C 0.52736(19) 0.69088(7) -0.1541(2) 0.0593(5) Uani 1 1 d . . . . .
H62 H 0.463040 0.683725 -0.229004 0.071 Uiso 1 1 calc R U . . .
C72 C 0.43563(14) 0.61979(5) -0.05292(13) 0.0328(3) Uani 1 1 d . . . . .
C82 C 0.39504(13) 0.54145(5) 0.05312(12) 0.0260(3) Uani 1 1 d . . . . .
C92 C 0.13582(12) 0.49541(4) 0.11245(12) 0.0249(3) Uani 1 1 d . . . . .
C102 C 0.08818(12) 0.44715(4) 0.15455(12) 0.0251(3) Uani 1 1 d . . . . .
C112 C 0.01512(14) 0.44674(5) 0.25907(12) 0.0302(3) Uani 1 1 d . . . . .
H112 H -0.007404 0.476559 0.296448 0.036 Uiso 1 1 calc R U . . .
C122 C -0.02494(16) 0.40335(5) 0.30895(14) 0.0360(3) Uani 1 1 d . . . . .
H122 H -0.075124 0.403429 0.379860 0.043 Uiso 1 1 calc R U . . .
C132 C 0.00848(17) 0.35974(5) 0.25499(15) 0.0393(3) Uani 1 1 d . . . . .
H132 H -0.016877 0.329879 0.290327 0.047 Uiso 1 1 calc R U . . .
C142 C 0.07850(17) 0.35968(5) 0.15008(16) 0.0416(4) Uani 1 1 d . . . . .
H142 H 0.099401 0.329771 0.112181 0.050 Uiso 1 1 calc R U . . .
C152 C 0.11858(15) 0.40317(5) 0.09960(14) 0.0344(3) Uani 1 1 d . . . . .
H152 H 0.166845 0.402899 0.027404 0.041 Uiso 1 1 calc R U . . .
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'
loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' -0.1026452 -0.0043155 -0.0085982 0.0136921 -0.0339744 0.0329923
0.0018495 0.0120140 0.0902101
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
C71 N11 C81 126.77(11) . . ?
C71 N11 H11N 122.2(10) . . ?
C81 N11 H11N 110.8(10) . . ?
C81 N21 N31 118.92(11) . . ?
C81 N21 H21N 120.6(12) . . ?
N31 N21 H21N 119.3(12) . . ?
C91 N31 N21 120.59(11) . . ?
C91 N31 H31N 123.9(10) . . ?
N21 N31 H31N 114.9(10) . . ?
C21 C11 C61 118.94(12) . . ?
C21 C11 C71 124.47(11) . . ?
C61 C11 C71 116.57(11) . . ?
C11 C21 C31 120.05(12) . . ?
C11 C21 H21 120.0 . . ?
C31 C21 H21 120.0 . . ?
C41 C31 C21 120.74(13) . . ?
C41 C31 H31 119.6 . . ?
C21 C31 H31 119.6 . . ?
C31 C41 C51 119.50(13) . . ?
C31 C41 H41 120.3 . . ?
C51 C41 H41 120.3 . . ?
C41 C51 C61 120.18(14) . . ?
C41 C51 H51 119.9 . . ?
C61 C51 H51 119.9 . . ?
C51 C61 C11 120.53(13) . . ?
C51 C61 H61 119.7 . . ?
C11 C61 H61 119.7 . . ?
O11 C71 N11 121.48(11) . . ?
O11 C71 C11 121.24(11) . . ?
N11 C71 C11 117.28(10) . . ?
O21 C81 N21 122.71(11) . . ?
O21 C81 N11 119.91(11) . . ?
N21 C81 N11 117.38(10) . . ?
O31 C91 N31 122.92(12) . . ?
O31 C91 C101 122.51(12) . . ?
N31 C91 C101 114.56(11) . . ?
C111 C101 C151 119.52(12) . . ?
C111 C101 C91 122.74(11) . . ?
C151 C101 C91 117.69(12) . . ?
C121 C111 C101 120.03(12) . . ?
C121 C111 H111 120.0 . . ?
C101 C111 H111 120.0 . . ?
C131 C121 C111 120.32(14) . . ?
C131 C121 H121 119.8 . . ?
C111 C121 H121 119.8 . . ?
C141 C131 C121 119.91(13) . . ?
C141 C131 H131 120.0 . . ?
C121 C131 H131 120.0 . . ?
C131 C141 C151 120.18(13) . . ?
C131 C141 H141 119.9 . . ?
C151 C141 H141 119.9 . . ?
C141 C151 C101 120.01(13) . . ?
C141 C151 H151 120.0 . . ?
C101 C151 H151 120.0 . . ?
C72 N12 C82 128.00(12) . . ?
C72 N12 H12N 119.8(10) . . ?
C82 N12 H12N 112.0(10) . . ?
C82 N22 N32 116.98(10) . . ?
C82 N22 H22N 123.4(11) . . ?
N32 N22 H22N 119.1(11) . . ?
C92 N32 N22 118.43(11) . . ?
C92 N32 H32N 123.0(11) . . ?
N22 N32 H32N 114.3(11) . . ?
C62 C12 C22 119.60(16) . . ?
C62 C12 C72 116.69(16) . . ?
C22 C12 C72 123.69(13) . . ?
C12 C22 C32 120.10(16) . . ?
C12 C22 H22 119.9 . . ?
C32 C22 H22 119.9 . . ?
C42 C32 C22 119.7(2) . . ?
C42 C32 H32 120.2 . . ?
C22 C32 H32 120.2 . . ?
C52 C42 C32 120.38(18) . . ?
C52 C42 H42 119.8 . . ?
C32 C42 H42 119.8 . . ?
C42 C52 C62 120.68(19) . . ?
C42 C52 H52 119.7 . . ?
C62 C52 H52 119.7 . . ?
C12 C62 C52 119.5(2) . . ?
C12 C62 H62 120.2 . . ?
C52 C62 H62 120.2 . . ?
O12 C72 N12 122.60(13) . . ?
O12 C72 C12 121.73(12) . . ?
N12 C72 C12 115.66(12) . . ?
O22 C82 N22 123.11(12) . . ?
O22 C82 N12 119.81(11) . . ?
N22 C82 N12 117.08(11) . . ?
O32 C92 N32 120.86(12) . . ?
O32 C92 C102 122.57(12) . . ?
N32 C92 C102 116.56(11) . . ?
C152 C102 C112 118.95(12) . . ?
C152 C102 C92 123.76(12) . . ?
C112 C102 C92 117.22(11) . . ?
C122 C112 C102 120.72(12) . . ?
C122 C112 H112 119.6 . . ?
C102 C112 H112 119.6 . . ?
C112 C122 C132 119.76(14) . . ?
C112 C122 H122 120.1 . . ?
C132 C122 H122 120.1 . . ?
C142 C132 C122 120.08(14) . . ?
C142 C132 H132 120.0 . . ?
C122 C132 H132 120.0 . . ?
C132 C142 C152 120.29(14) . . ?
C132 C142 H142 119.9 . . ?
C152 C142 H142 119.9 . . ?
C142 C152 C102 120.18(14) . . ?
C142 C152 H152 119.9 . . ?
C102 C152 H152 119.9 . . ?
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
O11 C71 1.2248(15) . ?
O21 C81 1.2361(14) . ?
O31 C91 1.2150(16) . ?
N11 C71 1.3814(16) . ?
N11 C81 1.3924(15) . ?
N11 H11N 0.902(17) . ?
N21 C81 1.3386(16) . ?
N21 N31 1.3872(14) . ?
N21 H21N 0.858(18) . ?
N31 C91 1.3559(16) . ?
N31 H31N 0.881(17) . ?
C11 C21 1.3859(18) . ?
C11 C61 1.3899(18) . ?
C11 C71 1.4958(17) . ?
C21 C31 1.3892(19) . ?
C21 H21 0.9500 . ?
C31 C41 1.375(2) . ?
C31 H31 0.9500 . ?
C41 C51 1.381(2) . ?
C41 H41 0.9500 . ?
C51 C61 1.386(2) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
C91 C101 1.5004(18) . ?
C101 C111 1.3899(19) . ?
C101 C151 1.3953(18) . ?
C111 C121 1.3867(19) . ?
C111 H111 0.9500 . ?
C121 C131 1.384(2) . ?
C121 H121 0.9500 . ?
C131 C141 1.383(2) . ?
C131 H131 0.9500 . ?
C141 C151 1.388(2) . ?
C141 H141 0.9500 . ?
C151 H151 0.9500 . ?
O12 C72 1.2205(18) . ?
O22 C82 1.2241(15) . ?
O32 C92 1.2245(15) . ?
N12 C72 1.3734(17) . ?
N12 C82 1.3929(17) . ?
N12 H12N 0.908(18) . ?
N22 C82 1.3522(16) . ?
N22 N32 1.3873(16) . ?
N22 H22N 0.903(18) . ?
N32 C92 1.3633(17) . ?
N32 H32N 0.901(18) . ?
C12 C62 1.392(2) . ?
C12 C22 1.392(2) . ?
C12 C72 1.496(2) . ?
C22 C32 1.397(2) . ?
C22 H22 0.9500 . ?
C32 C42 1.380(3) . ?
C32 H32 0.9500 . ?
C42 C52 1.372(4) . ?
C42 H42 0.9500 . ?
C52 C62 1.393(3) . ?
C52 H52 0.9500 . ?
C62 H62 0.9500 . ?
C92 C102 1.4966(17) . ?
C102 C152 1.3925(18) . ?
C102 C112 1.3946(19) . ?
C112 C122 1.384(2) . ?
C112 H112 0.9500 . ?
C122 C132 1.387(2) . ?
C122 H122 0.9500 . ?
C132 C142 1.380(2) . ?
C132 H132 0.9500 . ?
C142 C152 1.389(2) . ?
C142 H142 0.9500 . ?
C152 H152 0.9500 . ?
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
N11 H11N O22 0.902(17) 2.008(17) 2.9010(14) 170.6(14) . yes
N21 H21N O11 0.858(18) 1.973(17) 2.6174(14) 131.1(15) . yes
N31 H31N O32 0.881(17) 1.985(17) 2.8373(15) 162.3(15) 1_655 yes
N12 H12N O21 0.908(18) 1.937(18) 2.8325(14) 168.6(15) . yes
N22 H22N O12 0.903(18) 2.023(17) 2.6570(15) 126.1(14) . yes
N32 H32N O21 0.901(18) 2.044(18) 2.8922(15) 156.3(15) 3_665 yes
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
C81 N21 N31 C91 85.95(15) . . . . ?
C61 C11 C21 C31 -1.8(2) . . . . ?
C71 C11 C21 C31 179.71(13) . . . . ?
C11 C21 C31 C41 -0.5(2) . . . . ?
C21 C31 C41 C51 2.0(3) . . . . ?
C31 C41 C51 C61 -1.3(3) . . . . ?
C41 C51 C61 C11 -1.0(3) . . . . ?
C21 C11 C61 C51 2.5(2) . . . . ?
C71 C11 C61 C51 -178.89(15) . . . . ?
C81 N11 C71 O11 0.8(2) . . . . ?
C81 N11 C71 C11 -178.61(11) . . . . ?
C21 C11 C71 O11 -173.78(13) . . . . ?
C61 C11 C71 O11 7.67(19) . . . . ?
C21 C11 C71 N11 5.65(19) . . . . ?
C61 C11 C71 N11 -172.90(12) . . . . ?
N31 N21 C81 O21 -6.41(18) . . . . ?
N31 N21 C81 N11 173.53(10) . . . . ?
C71 N11 C81 O21 170.43(11) . . . . ?
C71 N11 C81 N21 -9.51(18) . . . . ?
N21 N31 C91 O31 6.1(2) . . . . ?
N21 N31 C91 C101 -175.04(11) . . . . ?
O31 C91 C101 C111 -149.10(14) . . . . ?
N31 C91 C101 C111 32.08(18) . . . . ?
O31 C91 C101 C151 28.45(19) . . . . ?
N31 C91 C101 C151 -150.37(13) . . . . ?
C151 C101 C111 C121 -0.3(2) . . . . ?
C91 C101 C111 C121 177.24(13) . . . . ?
C101 C111 C121 C131 1.3(2) . . . . ?
C111 C121 C131 C141 -1.0(2) . . . . ?
C121 C131 C141 C151 -0.4(2) . . . . ?
C131 C141 C151 C101 1.5(2) . . . . ?
C111 C101 C151 C141 -1.1(2) . . . . ?
C91 C101 C151 C141 -178.76(13) . . . . ?
C82 N22 N32 C92 68.96(15) . . . . ?
C62 C12 C22 C32 -0.4(2) . . . . ?
C72 C12 C22 C32 -178.74(14) . . . . ?
C12 C22 C32 C42 0.9(2) . . . . ?
C22 C32 C42 C52 -0.4(3) . . . . ?
C32 C42 C52 C62 -0.5(3) . . . . ?
C22 C12 C62 C52 -0.5(2) . . . . ?
C72 C12 C62 C52 177.93(16) . . . . ?
C42 C52 C62 C12 1.0(3) . . . . ?
C82 N12 C72 O12 -0.5(2) . . . . ?
C82 N12 C72 C12 178.17(12) . . . . ?
C62 C12 C72 O12 -19.8(2) . . . . ?
C22 C12 C72 O12 158.53(14) . . . . ?
C62 C12 C72 N12 161.50(13) . . . . ?
C22 C12 C72 N12 -20.1(2) . . . . ?
N32 N22 C82 O22 5.14(19) . . . . ?
N32 N22 C82 N12 -175.06(11) . . . . ?
C72 N12 C82 O22 177.87(13) . . . . ?
C72 N12 C82 N22 -1.9(2) . . . . ?
N22 N32 C92 O32 18.07(17) . . . . ?
N22 N32 C92 C102 -162.43(10) . . . . ?
O32 C92 C102 C152 -169.65(12) . . . . ?
N32 C92 C102 C152 10.85(18) . . . . ?
O32 C92 C102 C112 7.09(18) . . . . ?
N32 C92 C102 C112 -172.40(11) . . . . ?
C152 C102 C112 C122 0.97(19) . . . . ?
C92 C102 C112 C122 -175.94(12) . . . . ?
C102 C112 C122 C132 0.3(2) . . . . ?
C112 C122 C132 C142 -1.5(2) . . . . ?
C122 C132 C142 C152 1.4(2) . . . . ?
C132 C142 C152 C102 -0.1(2) . . . . ?
C112 C102 C152 C142 -1.1(2) . . . . ?
C92 C102 C152 C142 175.58(13) . . . . ?
