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#$Date: 2025-04-05 07:25:43 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299154 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/33/1573396.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_1573396
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         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-08-13 deposited with the CCDC.	2024-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9581(3)
_cell_length_b                   9.1704(3)
_cell_length_c                   27.6575(7)
_cell_measurement_reflns_used    17973
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      1.46
_cell_volume                     2525.68(13)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex3
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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  0.0623
_diffrn_reflns_av_unetI/netI     0.0365
_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       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            41429
_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         27.496
_diffrn_reflns_theta_min         1.473
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6502
_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    1.343
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0426P)²+0.9982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2119
_reflns_number_total             2887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4py01296h2.cif
_cod_data_source_block           l1330a
_cod_depositor_comments
'Adding full bibliography for 1573396--1573397.cif.'
_cod_original_cell_volume        2525.70(12)
_cod_database_code               1573396
_shelx_shelxl_version_number     2018/3
_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+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'
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 0.23621(12) 0.16138(11) 0.15441(4) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.40474(10) 0.26706(13) 0.24016(4) 0.0330(3) Uani 1 1 d . . . . .
N1 N 0.26847(14) 0.37966(15) 0.11617(5) 0.0278(3) Uani 1 1 d . . . . .
H1N H 0.2593(17) 0.473(2) 0.1204(6) 0.032(5) Uiso 1 1 d . . . . .
N2 N 0.19117(13) 0.37376(15) 0.19420(5) 0.0256(3) Uani 1 1 d . . . . .
H2N H 0.2216(17) 0.463(2) 0.1960(6) 0.029(5) Uiso 1 1 d . . . . .
N3 N 0.18126(13) 0.29706(14) 0.23740(5) 0.0256(3) Uani 1 1 d . . . . .
H3N H 0.0987(19) 0.2767(18) 0.2473(6) 0.032(5) Uiso 1 1 d . . . . .
C1 C 0.33319(15) 0.32942(17) 0.07360(6) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.30965(18) 0.4015(2) 0.03074(7) 0.0428(5) Uani 1 1 d . . . . .
H2 H 0.247348 0.479925 0.029749 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3768(2) 0.3598(3) -0.01096(7) 0.0585(6) Uani 1 1 d . . . . .
H3 H 0.359716 0.409568 -0.040462 0.070 Uiso 1 1 calc R U . . .
C4 C 0.4678(2) 0.2472(2) -0.00999(7) 0.0533(5) Uani 1 1 d . . . . .
H4 H 0.513072 0.218543 -0.038685 0.064 Uiso 1 1 calc R U . . .
C5 C 0.49247(19) 0.1768(2) 0.03274(7) 0.0443(5) Uani 1 1 d . . . . .
H5 H 0.555912 0.099435 0.033568 0.053 Uiso 1 1 calc R U . . .
C6 C 0.42655(17) 0.21646(18) 0.07463(7) 0.0352(4) Uani 1 1 d . . . . .
H6 H 0.444826 0.166857 0.104063 0.042 Uiso 1 1 calc R U . . .
C7 C 0.23549(14) 0.29554(16) 0.15449(5) 0.0241(3) Uani 1 1 d . . . . .
C8 C 0.29355(14) 0.23803(16) 0.25683(6) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.27498(15) 0.13479(16) 0.29809(6) 0.0260(3) Uani 1 1 d . . . . .
C10 C 0.15116(16) 0.07703(18) 0.31153(6) 0.0304(4) Uani 1 1 d . . . . .
H10 H 0.072112 0.105768 0.294826 0.036 Uiso 1 1 calc R U . . .
C11 C 0.14288(17) -0.02220(18) 0.34918(6) 0.0348(4) Uani 1 1 d . . . . .
H11 H 0.058050 -0.061174 0.358127 0.042 Uiso 1 1 calc R U . . .
C12 C 0.25700(18) -0.0650(2) 0.37384(6) 0.0371(4) Uani 1 1 d . . . . .
H12 H 0.250887 -0.132939 0.399672 0.044 Uiso 1 1 calc R U . . .
C13 C 0.38019(18) -0.0079(2) 0.36056(7) 0.0418(5) Uani 1 1 d . . . . .
H13 H 0.458941 -0.036778 0.377417 0.050 Uiso 1 1 calc R U . . .
C14 C 0.38950(17) 0.09063(19) 0.32297(6) 0.0354(4) Uani 1 1 d . . . . .
H14 H 0.474711 0.128597 0.314011 0.042 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' -0.0074831 -0.1087390 -0.0002171 0.0060870 -0.0011492 0.0360896
-0.0999593 0.0080704 0.0022139
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
C7 N1 C1 125.14(13) . . ?
C7 N1 H1N 115.5(12) . . ?
C1 N1 H1N 118.7(12) . . ?
C7 N2 N3 116.26(12) . . ?
C7 N2 H2N 114.9(11) . . ?
N3 N2 H2N 116.7(11) . . ?
C8 N3 N2 119.01(13) . . ?
C8 N3 H3N 124.1(11) . . ?
N2 N3 H3N 115.9(11) . . ?
C2 C1 C6 119.24(16) . . ?
C2 C1 N1 118.74(14) . . ?
C6 C1 N1 121.86(15) . . ?
C1 C2 C3 120.09(18) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.58(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.35(18) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.97(18) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.77(17) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 N1 124.62(14) . . ?
O1 C7 N2 121.44(14) . . ?
N1 C7 N2 113.82(13) . . ?
O2 C8 N3 120.60(15) . . ?
O2 C8 C9 122.37(14) . . ?
N3 C8 C9 117.02(13) . . ?
C14 C9 C10 118.87(15) . . ?
C14 C9 C8 117.41(14) . . ?
C10 C9 C8 123.67(14) . . ?
C11 C10 C9 120.21(15) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.56(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.39(17) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.47(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.50(16) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
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 C7 1.2303(18) . ?
O2 C8 1.2285(18) . ?
N1 C7 1.351(2) . ?
N1 C1 1.419(2) . ?
N1 H1N 0.87(2) . ?
N2 C7 1.3839(19) . ?
N2 N3 1.3900(18) . ?
N2 H2N 0.878(19) . ?
N3 C8 1.3536(19) . ?
N3 H3N 0.886(18) . ?
C1 C2 1.378(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.494(2) . ?
C9 C14 1.392(2) . ?
C9 C10 1.393(2) . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9500 . ?
C14 H14 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
N1 H1N O1 0.87(2) 1.97(2) 2.7919(17) 158.1(16) 8_665 yes
N2 H2N O1 0.878(19) 2.190(18) 2.9480(18) 144.4(14) 8_665 yes
N3 H3N O2 0.886(18) 1.965(19) 2.8361(17) 167.5(16) 6_556 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
C7 N2 N3 C8 61.83(18) . . . . ?
C7 N1 C1 C2 151.63(16) . . . . ?
C7 N1 C1 C6 -33.0(2) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
N1 C1 C2 C3 176.63(18) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
N1 C1 C6 C5 -176.38(16) . . . . ?
C1 N1 C7 O1 -13.0(2) . . . . ?
C1 N1 C7 N2 171.06(13) . . . . ?
N3 N2 C7 O1 16.2(2) . . . . ?
N3 N2 C7 N1 -167.70(13) . . . . ?
N2 N3 C8 O2 9.3(2) . . . . ?
N2 N3 C8 C9 -169.31(13) . . . . ?
O2 C8 C9 C14 10.9(2) . . . . ?
N3 C8 C9 C14 -170.58(14) . . . . ?
O2 C8 C9 C10 -166.60(15) . . . . ?
N3 C8 C9 C10 11.9(2) . . . . ?
C14 C9 C10 C11 0.3(2) . . . . ?
C8 C9 C10 C11 177.69(14) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C9 0.4(3) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
C8 C9 C14 C13 -178.08(15) . . . . ?
