#------------------------------------------------------------------------------
#$Date: 2023-07-05 14:06:11 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/86/1568697.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_1568697
loop_
_publ_author_name
'Horiuchi, Sachio'
'Minemawari, Hiromi'
'Ishibashi, Shoji'
_publ_section_title
;
 Competition of polar and antipolar states hidden behind a variety of
 polarization switching modes in hydrogen-bonded molecular chains.
;
_journal_issue                   6
_journal_name_full               'Materials horizons'
_journal_page_first              2149
_journal_page_last               2159
_journal_paper_doi               10.1039/d2mh01530g
_journal_volume                  10
_journal_year                    2023
_chemical_formula_moiety         'C7 H7 N5'
_chemical_formula_sum            'C7 H7 N5'
_chemical_formula_weight         161.17
_chemical_name_common            APHTZ
_chemical_name_systematic        5-(4-aminophenyl)-1H-tetrazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-02-21 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.087(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.2666(3)
_cell_length_b                   5.6858(2)
_cell_length_c                   15.5021(7)
_cell_measurement_reflns_used    5133
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.34
_cell_measurement_theta_min      2.75
_cell_volume                     728.50(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10608
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.628
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336.00
_exptl_crystal_preparation       ferroelectric
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.14
_refine_ls_abs_structure_details
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0502P)²+0.0410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0851
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                2586
_reflns_number_total             3133
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d2mh01530g2.cif
_cod_data_source_block           APHTZ
_cod_depositor_comments
'Adding full bibliography for 1568697--1568703.cif.'
_cod_database_code               1568697
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,-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
N1 N 0.2722(4) 0.0850(4) 0.3767(2) 0.0378(8) Uani 1 1 d . . . . .
N2 N 0.2475(4) -0.0828(5) 0.3163(2) 0.0456(9) Uani 1 1 d . . . . .
N3 N 0.3751(4) -0.2092(5) 0.3156(2) 0.0421(9) Uani 1 1 d . . . . .
N4 N 0.4848(4) -0.1273(5) 0.3766(2) 0.0329(7) Uani 1 1 d . . . . .
N5 N 0.6711(5) 0.5969(6) 0.6891(3) 0.0514(11) Uani 1 1 d . . . . .
N6 N 0.7862(4) 0.6136(5) 0.4016(2) 0.0342(8) Uani 1 1 d . . . . .
N7 N 0.8877(4) 0.6939(5) 0.4624(2) 0.0395(8) Uani 1 1 d . . . . .
N8 N 1.0133(4) 0.5550(5) 0.4633(3) 0.0425(8) Uani 1 1 d . . . . .
N9 N 0.9943(4) 0.3855(4) 0.4028(2) 0.0376(8) Uani 1 1 d . . . . .
N10 N 0.5897(5) -0.0939(6) 0.0841(3) 0.0506(11) Uani 1 1 d . . . . .
C1 C 0.4177(4) 0.0554(5) 0.4121(2) 0.0298(8) Uani 1 1 d . . . . .
C2 C 0.4840(4) 0.1992(5) 0.4832(2) 0.0275(8) Uani 1 1 d . . . . .
C3 C 0.4158(4) 0.4154(5) 0.5046(2) 0.0319(9) Uani 1 1 d . . . . .
H4 H 0.328441 0.472274 0.472215 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4754(4) 0.5458(5) 0.5726(3) 0.0354(10) Uani 1 1 d . . . . .
H5 H 0.426537 0.688036 0.586115 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6086(5) 0.4682(6) 0.6219(2) 0.0359(10) Uani 1 1 d . . . . .
C6 C 0.6793(4) 0.2542(6) 0.5984(3) 0.0387(9) Uani 1 1 d . . . . .
H6 H 0.769832 0.201180 0.629104 0.046 Uiso 1 1 calc R U . . .
C7 C 0.6195(4) 0.1212(6) 0.5318(3) 0.0367(9) Uani 1 1 d . . . . .
H7 H 0.668310 -0.021288 0.518463 0.044 Uiso 1 1 calc R U . . .
C8 C 0.8507(4) 0.4235(5) 0.3624(2) 0.0283(8) Uani 1 1 d . . . . .
C9 C 0.7784(4) 0.2868(5) 0.2934(2) 0.0283(8) Uani 1 1 d . . . . .
C10 C 0.6453(4) 0.3685(5) 0.2465(2) 0.0328(9) Uani 1 1 d . . . . .
H11 H 0.597276 0.509643 0.262370 0.039 Uiso 1 1 calc R U . . .
C11 C 0.5824(5) 0.2446(6) 0.1768(2) 0.0356(9) Uani 1 1 d . . . . .
H12 H 0.494549 0.304133 0.145406 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6513(4) 0.0296(6) 0.1537(2) 0.0314(9) Uani 1 1 d . . . . .
C13 C 0.7846(5) -0.0535(5) 0.2008(2) 0.0341(9) Uani 1 1 d . . . . .
H13 H 0.831649 -0.196149 0.185960 0.041 Uiso 1 1 calc R U . . .
C14 C 0.8472(4) 0.0736(5) 0.2691(3) 0.0310(9) Uani 1 1 d . . . . .
H14 H 0.936895 0.016441 0.299555 0.037 Uiso 1 1 calc R U . . .
H1 H 0.192(3) 0.183(5) 0.386(2) 0.052(9) Uiso 1 1 d . . . . .
H2 H 0.639(4) 0.726(5) 0.6955(19) 0.021(7) Uiso 1 1 d . . . . .
H3 H 0.747(6) 0.504(9) 0.734(3) 0.102(16) Uiso 1 1 d . . . . .
H8 H 0.690(3) 0.692(5) 0.3938(17) 0.038(7) Uiso 1 1 d . . . . .
H9 H 0.514(4) -0.048(5) 0.060(2) 0.026(7) Uiso 1 1 d . . . . .
H10 H 0.656(6) -0.216(8) 0.068(3) 0.11(2) Uiso 1 1 d . . . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 108.8(3) . . ?
C1 N1 H1 134(2) . . ?
N2 N1 H1 117(2) . . ?
N3 N2 N1 106.9(3) . . ?
N2 N3 N4 109.7(3) . . ?
C1 N4 N3 106.2(3) . . ?
C5 N5 H2 118(2) . . ?
C5 N5 H3 116(3) . . ?
H2 N5 H3 125(4) . . ?
N7 N6 C8 110.0(3) . . ?
N7 N6 H8 117.3(17) . . ?
C8 N6 H8 132.6(18) . . ?
N8 N7 N6 106.9(3) . . ?
N7 N8 N9 110.0(3) . . ?
C8 N9 N8 107.3(3) . . ?
C12 N10 H9 120(2) . . ?
C12 N10 H10 113(3) . . ?
H9 N10 H10 127(4) . . ?
N4 C1 N1 108.5(3) . . ?
N4 C1 C2 127.2(3) . . ?
N1 C1 C2 124.2(3) . . ?
C3 C2 C7 118.1(3) . . ?
C3 C2 C1 121.5(3) . . ?
C7 C2 C1 120.4(3) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H4 119.4 . . ?
C2 C3 H4 119.4 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H5 119.4 . . ?
C5 C4 H5 119.4 . . ?
N5 C5 C4 122.0(4) . . ?
N5 C5 C6 120.7(4) . . ?
C4 C5 C6 117.3(3) . . ?
C7 C6 C5 122.1(3) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C2 120.1(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N9 C8 N6 105.7(3) . . ?
N9 C8 C9 127.3(3) . . ?
N6 C8 C9 127.0(3) . . ?
C10 C9 C14 118.3(3) . . ?
C10 C9 C8 121.4(3) . . ?
C14 C9 C8 120.2(3) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H11 119.3 . . ?
C9 C10 H11 119.3 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H12 120.1 . . ?
C12 C11 H12 120.1 . . ?
N10 C12 C13 121.0(3) . . ?
N10 C12 C11 120.0(3) . . ?
C13 C12 C11 119.0(3) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
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
N1 C1 1.323(5) . ?
N1 N2 1.350(4) . ?
N1 H1 0.88(3) . ?
N2 N3 1.276(4) . ?
N3 N4 1.379(4) . ?
N4 C1 1.304(5) . ?
N5 C5 1.366(5) . ?
N5 H2 0.79(3) . ?
N5 H3 1.07(5) . ?
N6 N7 1.331(4) . ?
N6 C8 1.354(4) . ?
N6 H8 0.92(2) . ?
N7 N8 1.304(4) . ?
N8 N9 1.353(4) . ?
N9 C8 1.349(5) . ?
N10 C12 1.376(5) . ?
N10 H9 0.77(3) . ?
N10 H10 0.92(5) . ?
C1 C2 1.470(5) . ?
C2 C3 1.395(4) . ?
C2 C7 1.410(5) . ?
C3 C4 1.372(5) . ?
C3 H4 0.9300 . ?
C4 C5 1.400(5) . ?
C4 H5 0.9300 . ?
C5 C6 1.401(5) . ?
C6 C7 1.364(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.443(5) . ?
C9 C10 1.387(5) . ?
C9 C14 1.394(4) . ?
C10 C11 1.384(5) . ?
C10 H11 0.9300 . ?
C11 C12 1.398(5) . ?
C11 H12 0.9300 . ?
C12 C13 1.394(5) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N9 . . 1_455 2.897(4) 0.88(3) 2.02(3) 175(3) no
N6 H8 N4 . . 1_565 2.914(4) 0.92(2) 2.00(2) 178(2) no
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
C1 N1 N2 N3 0.0(4) . . . . ?
N1 N2 N3 N4 0.8(5) . . . . ?
N2 N3 N4 C1 -1.2(5) . . . . ?
C8 N6 N7 N8 -1.2(4) . . . . ?
N6 N7 N8 N9 0.5(4) . . . . ?
N7 N8 N9 C8 0.5(4) . . . . ?
N3 N4 C1 N1 1.2(4) . . . . ?
N3 N4 C1 C2 177.5(3) . . . . ?
N2 N1 C1 N4 -0.8(4) . . . . ?
N2 N1 C1 C2 -177.2(3) . . . . ?
N4 C1 C2 C3 167.6(4) . . . . ?
N1 C1 C2 C3 -16.7(6) . . . . ?
N4 C1 C2 C7 -12.3(6) . . . . ?
N1 C1 C2 C7 163.5(4) . . . . ?
C7 C2 C3 C4 -2.0(5) . . . . ?
C1 C2 C3 C4 178.2(3) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 N5 179.1(4) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
N5 C5 C6 C7 179.8(4) . . . . ?
C4 C5 C6 C7 -1.9(6) . . . . ?
C5 C6 C7 C2 1.0(6) . . . . ?
C3 C2 C7 C6 0.9(5) . . . . ?
C1 C2 C7 C6 -179.2(4) . . . . ?
N8 N9 C8 N6 -1.2(4) . . . . ?
N8 N9 C8 C9 -179.7(4) . . . . ?
N7 N6 C8 N9 1.5(4) . . . . ?
N7 N6 C8 C9 -180.0(3) . . . . ?
N9 C8 C9 C10 -167.7(4) . . . . ?
N6 C8 C9 C10 14.1(6) . . . . ?
N9 C8 C9 C14 8.7(6) . . . . ?
N6 C8 C9 C14 -169.5(3) . . . . ?
C14 C9 C10 C11 -0.7(5) . . . . ?
C8 C9 C10 C11 175.8(4) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C10 C11 C12 N10 -179.7(4) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
N10 C12 C13 C14 178.7(4) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
C12 C13 C14 C9 0.6(6) . . . . ?
C10 C9 C14 C13 -0.3(5) . . . . ?
C8 C9 C14 C13 -176.9(3) . . . . ?
