#------------------------------------------------------------------------------
#$Date: 2023-07-05 14:06:11 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/86/1568698.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_1568698
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 H5 F N4'
_chemical_formula_sum            'C7 H5 F N4'
_chemical_formula_weight         164.14
_chemical_name_common            FPHTZ
_chemical_name_systematic        5-(4-fluorophenyl)-1H-tetrazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/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                 92.037(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.0914(18)
_cell_length_b                   5.9622(13)
_cell_length_c                   14.789(4)
_cell_measurement_reflns_used    2263
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.70
_cell_volume                     713.0(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_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_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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       -19
_diffrn_reflns_number            7857
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         3.685
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             336.00
_exptl_crystal_preparation       ferroelectric-like
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.14
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0569P)²+0.0964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1455
_reflns_number_total             1620
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d2mh01530g2.cif
_cod_data_source_block           FPHTZ
_cod_depositor_comments
'Adding full bibliography for 1568697--1568703.cif.'
_cod_database_code               1568698
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -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
F1 F 1.04408(10) -0.36104(17) 0.70772(6) 0.0703(3) Uani 1 1 d . . . . .
N1 N 0.63656(12) 0.15744(18) 1.00947(7) 0.0446(3) Uani 1 1 d . . . . .
N2 N 0.61658(13) 0.32549(19) 1.06936(8) 0.0511(3) Uani 1 1 d . . . . .
N3 N 0.74509(12) 0.45353(19) 1.06860(7) 0.0487(3) Uani 1 1 d . . . . .
N4 N 0.84984(12) 0.37002(17) 1.00776(7) 0.0402(3) Uani 1 1 d . . . . .
C1 C 0.78165(13) 0.18684(19) 0.97142(7) 0.0353(3) Uani 1 1 d . . . . .
C2 C 0.85216(12) 0.04269(18) 0.90262(7) 0.0348(3) Uani 1 1 d . . . . .
C3 C 0.77608(13) -0.15941(19) 0.87924(8) 0.0394(3) Uani 1 1 d . . . . .
H3 H 0.680796 -0.202871 0.907934 0.047 Uiso 1 1 calc R U . . .
C4 C 0.84061(14) -0.2964(2) 0.81378(8) 0.0438(3) Uani 1 1 d . . . . .
H4 H 0.790210 -0.431862 0.798281 0.053 Uiso 1 1 calc R U . . .
C5 C 0.98110(14) -0.2273(2) 0.77220(8) 0.0460(3) Uani 1 1 d . . . . .
C6 C 1.06014(14) -0.0298(2) 0.79329(8) 0.0494(3) Uani 1 1 d . . . . .
H5 H 1.155135 0.012007 0.763951 0.059 Uiso 1 1 calc R U . . .
C7 C 0.99550(14) 0.1064(2) 0.85928(8) 0.0435(3) Uani 1 1 d . . . . .
H6 H 1.047715 0.240628 0.874781 0.052 Uiso 1 1 calc R U . . .
H1 H 0.564(3) 0.064(4) 1.0025(18) 0.041(7) Uiso 0.5 1 d . . P . .
H2 H 0.940(3) 0.435(4) 1.0007(17) 0.037(6) Uiso 0.5 1 d . . P . .
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)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 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 107.90(9) . . ?
C1 N1 H1 133.0(19) . . ?
N2 N1 H1 119.1(19) . . ?
N3 N2 N1 108.53(10) . . ?
N2 N3 N4 108.19(10) . . ?
C1 N4 N3 108.09(9) . . ?
C1 N4 H2 133.0(17) . . ?
N3 N4 H2 118.8(18) . . ?
N4 C1 N1 107.28(10) . . ?
N4 C1 C2 126.70(10) . . ?
N1 C1 C2 126.02(10) . . ?
C3 C2 C7 119.24(11) . . ?
C3 C2 C1 120.11(10) . . ?
C7 C2 C1 120.65(10) . . ?
C4 C3 C2 120.71(10) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.36(11) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
F1 C5 C6 118.77(11) . . ?
F1 C5 C4 118.40(12) . . ?
C6 C5 C4 122.83(11) . . ?
C5 C6 C7 118.60(11) . . ?
C5 C6 H5 120.7 . . ?
C7 C6 H5 120.7 . . ?
C6 C7 C2 120.26(11) . . ?
C6 C7 H6 119.9 . . ?
C2 C7 H6 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
F1 C5 1.3563(14) . ?
N1 C1 1.3313(14) . ?
N1 N2 1.3508(15) . ?
N1 H1 0.81(3) . ?
N2 N3 1.2903(14) . ?
N3 N4 1.3528(14) . ?
N4 C1 1.3285(14) . ?
N4 H2 0.84(2) . ?
C1 C2 1.4631(15) . ?
C2 C3 1.3911(15) . ?
C2 C7 1.3974(15) . ?
C3 C4 1.3829(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.3747(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3707(19) . ?
C6 C7 1.3861(17) . ?
C6 H5 0.9300 . ?
C7 H6 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 N1 . . 3_657 2.9056(15) 0.81(3) 2.09(3) 175(3) no
N4 H2 N4 . . 3_767 2.8982(15) 0.84(2) 2.06(2) 173(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 -0.27(15) . . . . ?
N1 N2 N3 N4 0.22(15) . . . . ?
N2 N3 N4 C1 -0.09(14) . . . . ?
N3 N4 C1 N1 -0.08(13) . . . . ?
N3 N4 C1 C2 -179.86(11) . . . . ?
N2 N1 C1 N4 0.21(13) . . . . ?
N2 N1 C1 C2 180.00(11) . . . . ?
N4 C1 C2 C3 171.83(10) . . . . ?
N1 C1 C2 C3 -7.92(17) . . . . ?
N4 C1 C2 C7 -8.59(18) . . . . ?
N1 C1 C2 C7 171.67(11) . . . . ?
C7 C2 C3 C4 -0.14(17) . . . . ?
C1 C2 C3 C4 179.45(10) . . . . ?
C2 C3 C4 C5 -0.32(17) . . . . ?
C3 C4 C5 F1 -179.73(10) . . . . ?
C3 C4 C5 C6 0.46(19) . . . . ?
F1 C5 C6 C7 -179.93(11) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C2 -0.36(19) . . . . ?
C3 C2 C7 C6 0.49(17) . . . . ?
C1 C2 C7 C6 -179.10(10) . . . . ?
