#------------------------------------------------------------------------------
#$Date: 2023-07-05 14:06:11 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/87/1568700.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_1568700
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         'C8 H8 N4'
_chemical_formula_sum            'C8 H8 N4'
_chemical_formula_weight         160.18
_chemical_name_common            MPHTZ
_chemical_name_systematic        5-p-tolyl-1H-tetrazole
_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   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                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   9.7712(5)
_cell_length_b                   9.0593(4)
_cell_length_c                   17.7198(10)
_cell_measurement_reflns_used    2714
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.86
_cell_measurement_theta_min      2.19
_cell_volume                     1568.56(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5586
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.104
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672.00
_exptl_crystal_preparation       antiferroelectric
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.17
_refine_ls_extinction_coef       0.0079(17)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0676P)²+0.3081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1326
_reflns_number_total             1783
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d2mh01530g2.cif
_cod_data_source_block           MPHTZ
_cod_depositor_comments
'Adding full bibliography for 1568697--1568703.cif.'
_cod_database_code               1568700
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -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 0.14657(10) 0.54608(11) 0.26608(6) 0.0358(3) Uani 1 1 d . . . . .
N2 N 0.19056(11) 0.64016(13) 0.31965(6) 0.0417(3) Uani 1 1 d . . . . .
N3 N 0.32235(11) 0.63358(13) 0.31899(6) 0.0433(3) Uani 1 1 d . . . . .
N4 N 0.36548(9) 0.53668(12) 0.26530(6) 0.0388(3) Uani 1 1 d . . . . .
C1 C 0.25418(10) 0.48306(14) 0.23254(7) 0.0317(3) Uani 1 1 d . . . . .
C2 C 0.24921(10) 0.37648(14) 0.17074(7) 0.0344(3) Uani 1 1 d . . . . .
C3 C 0.37010(12) 0.32038(15) 0.14042(8) 0.0433(4) Uani 1 1 d . . . . .
H2 H 0.453878 0.348590 0.160723 0.052 Uiso 1 1 calc R U . . .
C4 C 0.36630(14) 0.22330(15) 0.08051(8) 0.0488(4) Uani 1 1 d . . . . .
H3 H 0.447942 0.186546 0.061150 0.059 Uiso 1 1 calc R U . . .
C5 C 0.24335(14) 0.17930(16) 0.04850(8) 0.0475(4) Uani 1 1 d . . . . .
C6 C 0.12340(14) 0.23110(16) 0.08085(8) 0.0488(4) Uani 1 1 d . . . . .
H4 H 0.039729 0.199601 0.061705 0.059 Uiso 1 1 calc R U . . .
C7 C 0.12531(12) 0.32845(15) 0.14090(7) 0.0430(4) Uani 1 1 d . . . . .
H5 H 0.043417 0.361976 0.161434 0.052 Uiso 1 1 calc R U . . .
C8 C 0.24063(17) 0.0797(2) -0.01932(10) 0.0651(5) Uani 1 1 d . . . . .
H6A H 0.318980 0.015807 -0.018333 0.078 Uiso 1 1 calc R U . . .
H7B H 0.242552 0.138354 -0.064436 0.078 Uiso 1 1 calc R U . . .
H8C H 0.158626 0.021379 -0.018516 0.078 Uiso 1 1 calc R U . . .
H1 H 0.048(2) 0.5393(19) 0.2547(9) 0.069(5) 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 109.44(10) . . ?
C1 N1 H1 130.6(10) . . ?
N2 N1 H1 119.7(10) . . ?
N3 N2 N1 106.46(9) . . ?
N2 N3 N4 110.21(9) . . ?
C1 N4 N3 106.77(9) . . ?
N4 C1 N1 107.13(11) . . ?
N4 C1 C2 126.73(10) . . ?
N1 C1 C2 126.14(9) . . ?
C7 C2 C3 118.50(13) . . ?
C7 C2 C1 121.38(10) . . ?
C3 C2 C1 120.12(10) . . ?
C4 C3 C2 120.43(12) . . ?
C4 C3 H2 119.8 . . ?
C2 C3 H2 119.8 . . ?
C3 C4 C5 121.42(12) . . ?
C3 C4 H3 119.3 . . ?
C5 C4 H3 119.3 . . ?
C6 C5 C4 117.76(14) . . ?
C6 C5 C8 121.25(13) . . ?
C4 C5 C8 120.98(13) . . ?
C7 C6 C5 121.52(12) . . ?
C7 C6 H4 119.2 . . ?
C5 C6 H4 119.2 . . ?
C6 C7 C2 120.27(12) . . ?
C6 C7 H5 119.9 . . ?
C2 C7 H5 119.9 . . ?
C5 C8 H6A 109.5 . . ?
C5 C8 H7B 109.5 . . ?
H6A C8 H7B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H6A C8 H8C 109.5 . . ?
H7B C8 H8C 109.5 . . ?
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 1.3359(14) . ?
N1 N2 1.3462(15) . ?
N1 H1 0.98(2) . ?
N2 N3 1.2891(16) . ?
N3 N4 1.3613(15) . ?
N4 C1 1.3250(14) . ?
C1 C2 1.4608(18) . ?
C2 C7 1.3909(16) . ?
C2 C3 1.3937(16) . ?
C3 C4 1.3791(19) . ?
C3 H2 0.9300 . ?
C4 C5 1.387(2) . ?
C4 H3 0.9300 . ?
C5 C6 1.3866(19) . ?
C5 C8 1.503(2) . ?
C6 C7 1.3822(19) . ?
C6 H4 0.9300 . ?
C7 H5 0.9300 . ?
C8 H6A 0.9600 . ?
C8 H7B 0.9600 . ?
C8 H8C 0.9600 . ?
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 N4 . . 8_556 2.8036(13) 0.98(2) 1.82(2) 177.1(15) 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 -0.43(13) . . . . ?
N1 N2 N3 N4 0.28(13) . . . . ?
N2 N3 N4 C1 -0.04(13) . . . . ?
N3 N4 C1 N1 -0.23(13) . . . . ?
N3 N4 C1 C2 179.09(11) . . . . ?
N2 N1 C1 N4 0.41(14) . . . . ?
N2 N1 C1 C2 -178.91(11) . . . . ?
N4 C1 C2 C7 -179.93(12) . . . . ?
N1 C1 C2 C7 -0.74(19) . . . . ?
N4 C1 C2 C3 0.2(2) . . . . ?
N1 C1 C2 C3 179.37(11) . . . . ?
C7 C2 C3 C4 2.2(2) . . . . ?
C1 C2 C3 C4 -177.94(11) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -2.8(2) . . . . ?
C3 C4 C5 C8 176.78(13) . . . . ?
C4 C5 C6 C7 2.8(2) . . . . ?
C8 C5 C6 C7 -176.77(13) . . . . ?
C5 C6 C7 C2 -0.3(2) . . . . ?
C3 C2 C7 C6 -2.2(2) . . . . ?
C1 C2 C7 C6 177.95(12) . . . . ?
