# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_APHTZ
_database_code_depnum_ccdc_archive 'CCDC 2226486'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C7 H7 N5'
_chemical_formula_moiety         'C7 H7 N5'
_chemical_formula_weight         161.17
_chemical_melting_point          ?
_chemical_absolute_configuration .
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)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
_space_group_IT_number           7
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.2666(3)
_cell_length_b                   5.6858(2)
_cell_length_c                   15.5021(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.087(4)
_cell_angle_gamma                90.0000
_cell_volume                     728.50(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5133
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      29.34
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.085
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336.00
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            10608
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.628
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3133
_reflns_number_gt                2586
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_max     0.873
_reflns_Friedel_fraction_full    0.910

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0807
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     242
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0502P)²+0.0410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(4)
_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)


#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

#==============================================================================
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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5-(4-aminophenyl)-1H-tetrazole
_chemical_name_common            APHTZ
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       ferroelectric
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FPHTZ
_database_code_depnum_ccdc_archive 'CCDC 2226488'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C7 H5 F N4'
_chemical_formula_moiety         'C7 H5 F N4'
_chemical_formula_weight         164.14
_chemical_melting_point          ?
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)
;
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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
#------------------------------------------------------------------------------
_cell_length_a                   8.0914(18)
_cell_length_b                   5.9622(13)
_cell_length_c                   14.789(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.037(5)
_cell_angle_gamma                90.0000
_cell_volume                     713.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2263
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336.00
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.988

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            7857
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         3.685
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1620
_reflns_number_gt                1455
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1043
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1620
_refine_ls_number_parameters     118
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0569P)²+0.0964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(4)



#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5-(4-fluorophenyl)-1H-tetrazole
_chemical_name_common            FPHTZ
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       ferroelectric-like
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_CPHTZ
_database_code_depnum_ccdc_archive 'CCDC 2226487'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C7 H5 Cl N4'
_chemical_formula_moiety         'C7 H5 Cl N4'
_chemical_formula_weight         180.60
_chemical_melting_point          ?
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)
;
Cl Cl 0.1484 0.1585
;
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)
;
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
_space_group_IT_number           13
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.457(3)
_cell_length_b                   11.427(3)
_cell_length_c                   7.298(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.987(6)
_cell_angle_gamma                90.0000
_cell_volume                     750.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2045
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368.00
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.914

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            6603
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_theta_max         27.629
_diffrn_reflns_theta_min         3.434
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1728
_reflns_number_gt                1504
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1119
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1728
_refine_ls_number_parameters     122
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0600P)²+0.1030P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.024(4)



#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.000000 0.42394(5) 0.250000 0.0508(2) Uani 1 2 d S T P . .
Cl2 Cl 0.500000 0.72523(5) 0.250000 0.0482(2) Uani 1 2 d S T P . .
N1 N 0.11056(16) -0.16708(11) 0.3489(2) 0.0366(3) Uani 1 1 d . . . . .
N2 N 0.06625(16) -0.27920(11) 0.3099(2) 0.0440(4) Uani 1 1 d . . . . .
N3 N 0.60590(15) 0.13437(11) 0.35918(19) 0.0365(3) Uani 1 1 d . . . . .
N4 N 0.56424(15) 0.02215(11) 0.3162(2) 0.0413(3) Uani 1 1 d . . . . .
C1 C 0.000000 -0.09841(18) 0.250000 0.0309(4) Uani 1 2 d S T P . .
C2 C 0.000000 0.03029(16) 0.250000 0.0279(4) Uani 1 2 d S T P . .
C3 C 0.12343(16) 0.09158(13) 0.3608(2) 0.0348(3) Uani 1 1 d . . . . .
H2 H 0.206627 0.050973 0.435140 0.042 Uiso 1 1 calc R U . . .
C4 C 0.12372(16) 0.21288(14) 0.3617(2) 0.0378(4) Uani 1 1 d . . . . .
H3 H 0.206414 0.253731 0.436720 0.045 Uiso 1 1 calc R U . . .
C5 C 0.000000 0.27253(17) 0.250000 0.0338(4) Uani 1 2 d S T P . .
C6 C 0.500000 0.20317(18) 0.250000 0.0302(4) Uani 1 2 d S T P . .
C7 C 0.500000 0.33179(16) 0.250000 0.0294(4) Uani 1 2 d S T P . .
C8 C 0.63082(16) 0.39297(14) 0.3311(2) 0.0379(4) Uani 1 1 d . . . . .
H5 H 0.718785 0.352332 0.387166 0.045 Uiso 1 1 calc R U . . .
C9 C 0.63178(18) 0.51396(14) 0.3296(2) 0.0411(4) Uani 1 1 d . . . . .
H6 H 0.720121 0.554907 0.381472 0.049 Uiso 1 1 calc R U . . .
C10 C 0.500000 0.57299(17) 0.250000 0.0329(4) Uani 1 2 d S T P . .
H1 H 0.181(4) -0.151(3) 0.422(5) 0.033(9) Uiso 0.5 1 d . . P . .
H4 H 0.676(4) 0.145(3) 0.445(5) 0.025(8) Uiso 0.5 1 d . . P . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cl1 C5 1.730(2) . ?
Cl2 C10 1.740(2) . ?
N1 C1 1.3281(18) . ?
N1 N2 1.3507(18) . ?
N1 H1 0.74(4) . ?
N2 N2 1.288(3) 2 ?
N3 C6 1.3278(18) . ?
N3 N4 1.3497(18) . ?
N3 H4 0.76(4) . ?
N4 N4 1.298(3) 2_655 ?
C1 C2 1.471(3) . ?
C2 C3 1.3871(17) . ?
C2 C3 1.3872(17) 2 ?
C3 C4 1.386(2) . ?
C3 H2 0.9300 . ?
C4 C5 1.3816(18) . ?
C4 H3 0.9300 . ?
C6 C7 1.470(3) . ?
C7 C8 1.3847(18) 2_655 ?
C7 C8 1.3847(18) . ?
C8 C9 1.383(2) . ?
C8 H5 0.9300 . ?
C9 C10 1.3779(19) . ?
C9 H6 0.9300 . ?

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 107.76(14) . . ?
C1 N1 H1 129(3) . . ?
N2 N1 H1 123(3) . . ?
N2 N2 N1 108.46(8) 2 . ?
C6 N3 N4 108.12(13) . . ?
C6 N3 H4 134(2) . . ?
N4 N3 H4 117(2) . . ?
N4 N4 N3 108.18(8) 2_655 . ?
N1 C1 N1 107.56(19) 2 . ?
N1 C1 C2 126.22(9) 2 . ?
N1 C1 C2 126.22(9) . . ?
C3 C2 C3 119.35(18) . 2 ?
C3 C2 C1 120.32(9) . . ?
C3 C2 C1 120.33(9) 2 . ?
C4 C3 C2 120.51(14) . . ?
C4 C3 H2 119.7 . . ?
C2 C3 H2 119.7 . . ?
C5 C4 C3 119.38(14) . . ?
C5 C4 H3 120.3 . . ?
C3 C4 H3 120.3 . . ?
C4 C5 C4 120.88(19) 2 . ?
C4 C5 Cl1 119.56(9) 2 . ?
C4 C5 Cl1 119.56(9) . . ?
N3 C6 N3 107.39(18) 2_655 . ?
N3 C6 C7 126.31(9) 2_655 . ?
N3 C6 C7 126.30(9) . . ?
C8 C7 C8 119.35(18) 2_655 . ?
C8 C7 C6 120.32(9) 2_655 . ?
C8 C7 C6 120.32(9) . . ?
C9 C8 C7 120.57(14) . . ?
C9 C8 H5 119.7 . . ?
C7 C8 H5 119.7 . . ?
C10 C9 C8 119.05(14) . . ?
C10 C9 H6 120.5 . . ?
C8 C9 H6 120.5 . . ?
C9 C10 C9 121.37(19) . 2_655 ?
C9 C10 Cl2 119.31(10) . . ?
C9 C10 Cl2 119.31(10) 2_655 . ?

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 N2 0.5(2) . . . 2 ?
C6 N3 N4 N4 0.0(2) . . . 2_655 ?
N2 N1 C1 N1 -0.19(8) . . . 2 ?
N2 N1 C1 C2 179.81(8) . . . . ?
N1 C1 C2 C3 179.86(11) 2 . . . ?
N1 C1 C2 C3 -0.15(11) . . . . ?
N1 C1 C2 C3 -0.15(10) 2 . . 2 ?
N1 C1 C2 C3 179.85(10) . . . 2 ?
C3 C2 C3 C4 0.19(10) 2 . . . ?
C1 C2 C3 C4 -179.81(10) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C4 0.19(10) . . . 2 ?
C3 C4 C5 Cl1 -179.81(10) . . . . ?
N4 N3 C6 N3 0.01(8) . . . 2_655 ?
N4 N3 C6 C7 -179.99(8) . . . . ?
N3 C6 C7 C8 16.98(11) 2_655 . . 2_655 ?
N3 C6 C7 C8 -163.02(11) . . . 2_655 ?
N3 C6 C7 C8 -163.02(11) 2_655 . . . ?
N3 C6 C7 C8 16.98(11) . . . . ?
C8 C7 C8 C9 -0.75(11) 2_655 . . . ?
C6 C7 C8 C9 179.25(11) . . . . ?
C7 C8 C9 C10 1.5(2) . . . . ?
C8 C9 C10 C9 -0.73(11) . . . 2_655 ?
C8 C9 C10 Cl2 179.27(11) . . . . ?

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 N3 . . 3_656 2.8881(19) 0.74(3) 2.16(3) 170(4) no
N3 H4 N1 . . 3_656 2.8881(19) 0.76(3) 2.13(3) 171(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5-(4-chlorophenyl)-1H-tetrazole
_chemical_name_common            CPHTZ
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       ferroelectric-like
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MPHTZ
_database_code_depnum_ccdc_archive 'CCDC 2226489'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C8 H8 N4'
_chemical_formula_moiety         'C8 H8 N4'
_chemical_formula_weight         160.18
_chemical_melting_point          ?
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)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
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
#------------------------------------------------------------------------------
_cell_length_a                   9.7712(5)
_cell_length_b                   9.0593(4)
_cell_length_c                   17.7198(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1568.56(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2714
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      29.86
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672.00
_exptl_absorpt_coefficient_mu    0.090
_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_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.989

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            5586
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.104
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1783
_reflns_number_gt                1326
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1334
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1783
_refine_ls_number_parameters     115
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0676P)²+0.3081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0079(17)


#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

#==============================================================================
# start Validation Reply Form
_vrf_PLAT110_MPHTZ               
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: ...
;
_vrf_PLAT112_MPHTZ               
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: ...
;
_vrf_PLAT113_MPHTZ               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Pbcm Check 
RESPONSE: The superlattice formed by antipolar ordering of NH 
          hydrogen is supported by the antiferroelectric P-E curve.
;
# end Validation Reply Form

# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5-p-tolyl-1H-tetrazole
_chemical_name_common            MPHTZ
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       antiferroelectric
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DM-BIM
_database_code_depnum_ccdc_archive 'CCDC 2226492'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C5 H7 Br N2'
_chemical_formula_moiety         'C5 H7 Br N2'
_chemical_formula_weight         175.03
_chemical_melting_point          ?
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)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'
_space_group_IT_number           57
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 +X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
5 -X,-Y,-Z
6 +X,+Y,-1/2-Z
7 -X,-1/2+Y,+Z
8 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   4.0674(3)
_cell_length_b                   16.0311(8)
_cell_length_c                   10.1239(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     660.13(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1750
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.81
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.214
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344.00
_exptl_absorpt_coefficient_mu    6.139
_exptl_absorpt_correction_T_min  0.119
_exptl_absorpt_correction_T_max  0.536
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.768
_oxdiff_exptl_absorpt_empirical_full_max 1.310
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            3547
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             804
_reflns_number_gt                642
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0753
_refine_ls_wR_factor_gt          0.0716
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         804
_refine_ls_number_parameters     45
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0434P)²+0.1046P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?


#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br1 Br -0.11848(11) 0.37575(2) 0.250000 0.05449(19) Uani 1 2 d S T P . .
N1 N 0.1451(5) 0.22874(12) 0.14090(18) 0.0387(5) Uani 1 1 d . . . . .
C1 C 0.0686(8) 0.26945(19) 0.250000 0.0373(7) Uani 1 2 d S T P . .
C2 C 0.2837(6) 0.15475(15) 0.1832(2) 0.0372(5) Uani 1 1 d . . . . .
C3 C 0.4044(8) 0.09078(19) 0.0877(3) 0.0541(7) Uani 1 1 d . . . . .
H1A H 0.533070 0.049890 0.133823 0.065 Uiso 1 1 calc R U . . .
H2B H 0.537529 0.117265 0.021606 0.065 Uiso 1 1 calc R U . . .
H3C H 0.220087 0.064037 0.046276 0.065 Uiso 1 1 calc R U . . .
H4 H 0.107(10) 0.244(3) 0.067(4) 0.029(12) Uiso 0.5 1 d . . P . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C1 1.866(3) . ?
N1 C1 1.320(2) . ?
N1 C2 1.382(3) . ?
N1 H4 0.81(4) . ?
C2 C2 1.352(4) 6_556 ?
C2 C3 1.493(4) . ?
C3 H1A 0.9600 . ?
C3 H2B 0.9600 . ?
C3 H3C 0.9600 . ?

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 C2 105.13(19) . . ?
C1 N1 H4 126(3) . . ?
C2 N1 H4 129(3) . . ?
N1 C1 N1 113.6(3) . 6_556 ?
N1 C1 Br1 123.20(14) . . ?
N1 C1 Br1 123.20(14) 6_556 . ?
C2 C2 N1 108.08(12) 6_556 . ?
C2 C2 C3 130.39(15) 6_556 . ?
N1 C2 C3 121.5(2) . . ?
C2 C3 H1A 109.5 . . ?
C2 C3 H2B 109.5 . . ?
H1A C3 H2B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H1A C3 H3C 109.5 . . ?
H2B C3 H3C 109.5 . . ?

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
C2 N1 C1 N1 0.1(4) . . . 6_556 ?
C2 N1 C1 Br1 178.4(2) . . . . ?
C1 N1 C2 C2 0.0(2) . . . 6_556 ?
C1 N1 C2 C3 -179.9(3) . . . . ?

#==============================================================================
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 H4 N1 . . 3_555 2.933(3) 0.81(4) 2.15(4) 164(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        2-Bromo-4,5-dimethyl-1H-imidazole
_chemical_name_common            DM-BIM
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TFPHTZ
_database_code_depnum_ccdc_archive 'CCDC 2226491'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C8 H5 F3 N4'
_chemical_formula_moiety         'C8 H5 F3 N4'
_chemical_formula_weight         214.15
_chemical_melting_point          ?

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)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.3316(19)
_cell_length_b                   9.7732(16)
_cell_length_c                   9.7411(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 116.898(3)
_cell_angle_gamma                90.0000
_cell_volume                     877.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2808
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432.00
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            7181
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.039
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1982
_reflns_number_gt                1770
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1277
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1982
_refine_ls_number_parameters     168
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0734P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.007
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.059(8)


#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.4560(5) 0.2056(5) 0.2611(17) 0.166(4) Uani 0.42 1 d . . P . .
F2 F 0.5859(7) 0.3595(8) 0.3887(6) 0.1201(18) Uani 0.42 1 d . . P . .
F3 F 0.5681(10) 0.3244(11) 0.1757(10) 0.141(3) Uani 0.42 1 d . . P . .
F4 F 0.4952(8) 0.2542(8) 0.3601(7) 0.143(2) Uani 0.58 1 d . . P . .
F5 F 0.6100(3) 0.3821(3) 0.2851(11) 0.1442(19) Uani 0.58 1 d . . P . .
F6 F 0.4761(6) 0.2306(5) 0.1430(4) 0.1203(12) Uani 0.58 1 d . . P . .
N1 N -0.02275(12) 0.77932(11) -0.12746(11) 0.0464(3) Uani 1 1 d . . . . .
N2 N -0.12184(13) 0.87377(12) -0.13275(12) 0.0528(3) Uani 1 1 d . . . . .
N3 N -0.12962(13) 0.87419(11) -0.00444(12) 0.0511(3) Uani 1 1 d . . . . .
N4 N -0.03466(11) 0.77933(10) 0.08595(11) 0.0432(3) Uani 1 1 d . . . . .
C1 C 0.03077(12) 0.72136(11) 0.01001(12) 0.0377(3) Uani 1 1 d . . . . .
C2 C 0.14313(12) 0.61565(11) 0.06954(12) 0.0395(3) Uani 1 1 d . . . . .
C3 C 0.19506(14) 0.56674(13) 0.21943(14) 0.0481(3) Uani 1 1 d . . . . .
H2 H 0.155496 0.598969 0.282114 0.058 Uiso 1 1 calc R U . . .
C4 C 0.30480(15) 0.47082(14) 0.27552(15) 0.0531(3) Uani 1 1 d . . . . .
H3 H 0.338891 0.438406 0.375651 0.064 Uiso 1 1 calc R U . . .
C5 C 0.36401(14) 0.42294(13) 0.18288(15) 0.0501(3) Uani 1 1 d . . . . .
C6 C 0.31037(15) 0.46778(15) 0.03168(16) 0.0549(4) Uani 1 1 d . . . . .
H4 H 0.348273 0.433200 -0.031527 0.066 Uiso 1 1 calc R U . . .
C7 C 0.20081(15) 0.56365(14) -0.02427(14) 0.0497(3) Uani 1 1 d . . . . .
H5 H 0.165096 0.593885 -0.125396 0.060 Uiso 1 1 calc R U . . .
C8 C 0.48852(18) 0.32476(17) 0.2464(2) 0.0676(4) Uani 1 1 d . . . . .
H1 H -0.0272(17) 0.7610(18) 0.1862(18) 0.068(5) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 F4 0.983(8) . ?
F1 C8 1.238(4) . ?
F1 F6 1.282(10) . ?
F2 F5 1.165(6) . ?
F2 F4 1.334(6) . ?
F2 C8 1.337(4) . ?
F3 F5 1.106(7) . ?
F3 F6 1.253(8) . ?
F3 C8 1.289(4) . ?
F4 C8 1.280(3) . ?
F5 C8 1.266(3) . ?
F6 C8 1.327(3) . ?
N1 C1 1.3228(14) . ?
N1 N2 1.3620(16) . ?
N2 N3 1.2883(15) . ?
N3 N4 1.3474(15) . ?
N4 C1 1.3333(14) . ?
N4 H1 0.961(15) . ?
C1 C2 1.4636(16) . ?
C2 C3 1.3926(16) . ?
C2 C7 1.3933(16) . ?
C3 C4 1.3793(18) . ?
C3 H2 0.9300 . ?
C4 C5 1.3809(18) . ?
C4 H3 0.9300 . ?
C5 C6 1.3892(19) . ?
C5 C8 1.496(2) . ?
C6 C7 1.3777(18) . ?
C6 H4 0.9300 . ?
C7 H5 0.9300 . ?

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
F4 F1 C8 69.3(4) . . ?
F4 F1 F6 128.8(6) . . ?
C8 F1 F6 63.5(4) . . ?
F5 F2 F4 111.8(4) . . ?
F5 F2 C8 60.3(2) . . ?
F4 F2 C8 57.3(2) . . ?
F5 F3 F6 122.7(5) . . ?
F5 F3 C8 63.3(3) . . ?
F6 F3 C8 62.9(3) . . ?
F1 F4 C8 64.8(4) . . ?
F1 F4 F2 121.1(6) . . ?
C8 F4 F2 61.5(3) . . ?
F3 F5 F2 126.4(6) . . ?
F3 F5 C8 65.4(3) . . ?
F2 F5 C8 66.6(3) . . ?
F3 F6 F1 108.9(4) . . ?
F3 F6 C8 59.9(2) . . ?
F1 F6 C8 56.6(3) . . ?
C1 N1 N2 106.94(9) . . ?
N3 N2 N1 109.95(10) . . ?
N2 N3 N4 106.57(10) . . ?
C1 N4 N3 109.38(9) . . ?
C1 N4 H1 131.0(10) . . ?
N3 N4 H1 119.5(10) . . ?
N1 C1 N4 107.16(10) . . ?
N1 C1 C2 126.64(10) . . ?
N4 C1 C2 126.19(10) . . ?
C3 C2 C7 119.10(12) . . ?
C3 C2 C1 121.20(10) . . ?
C7 C2 C1 119.70(10) . . ?
C4 C3 C2 120.42(11) . . ?
C4 C3 H2 119.8 . . ?
C2 C3 H2 119.8 . . ?
C3 C4 C5 119.95(12) . . ?
C3 C4 H3 120.0 . . ?
C5 C4 H3 120.0 . . ?
C4 C5 C6 120.25(12) . . ?
C4 C5 C8 119.96(13) . . ?
C6 C5 C8 119.77(13) . . ?
C7 C6 C5 119.75(12) . . ?
C7 C6 H4 120.1 . . ?
C5 C6 H4 120.1 . . ?
C6 C7 C2 120.48(11) . . ?
C6 C7 H5 119.8 . . ?
C2 C7 H5 119.8 . . ?
F1 C8 F5 131.8(3) . . ?
F1 C8 F4 45.9(4) . . ?
F5 C8 F4 108.8(4) . . ?
F1 C8 F3 109.3(5) . . ?
F5 C8 F3 51.3(4) . . ?
F4 C8 F3 131.5(3) . . ?
F1 C8 F6 59.8(5) . . ?
F5 C8 F6 106.0(3) . . ?
F4 C8 F6 103.4(3) . . ?
F3 C8 F6 57.2(4) . . ?
F1 C8 F2 103.6(4) . . ?
F5 C8 F2 53.1(3) . . ?
F4 C8 F2 61.2(3) . . ?
F3 C8 F2 101.0(4) . . ?
F6 C8 F2 137.0(2) . . ?
F1 C8 C5 115.0(3) . . ?
F5 C8 C5 112.97(19) . . ?
F4 C8 C5 113.8(2) . . ?
F3 C8 C5 114.7(2) . . ?
F6 C8 C5 111.19(18) . . ?
F2 C8 C5 111.6(2) . . ?

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
F6 F1 F4 C8 23.7(6) . . . . ?
C8 F1 F4 F2 -25.9(5) . . . . ?
F6 F1 F4 F2 -2.1(10) . . . . ?
F5 F2 F4 F1 -0.4(7) . . . . ?
C8 F2 F4 F1 26.7(5) . . . . ?
F5 F2 F4 C8 -27.1(3) . . . . ?
F6 F3 F5 F2 6.3(7) . . . . ?
C8 F3 F5 F2 28.2(4) . . . . ?
F6 F3 F5 C8 -21.9(4) . . . . ?
F4 F2 F5 F3 -1.8(6) . . . . ?
C8 F2 F5 F3 -28.0(4) . . . . ?
F4 F2 F5 C8 26.2(3) . . . . ?
F5 F3 F6 F1 -7.5(6) . . . . ?
C8 F3 F6 F1 -29.5(3) . . . . ?
F5 F3 F6 C8 22.0(4) . . . . ?
F4 F1 F6 F3 5.8(8) . . . . ?
C8 F1 F6 F3 30.7(3) . . . . ?
F4 F1 F6 C8 -24.9(6) . . . . ?
C1 N1 N2 N3 -0.12(14) . . . . ?
N1 N2 N3 N4 0.09(14) . . . . ?
N2 N3 N4 C1 -0.03(14) . . . . ?
N2 N1 C1 N4 0.09(13) . . . . ?
N2 N1 C1 C2 -178.62(10) . . . . ?
N3 N4 C1 N1 -0.04(13) . . . . ?
N3 N4 C1 C2 178.69(10) . . . . ?
N1 C1 C2 C3 177.18(11) . . . . ?
N4 C1 C2 C3 -1.31(18) . . . . ?
N1 C1 C2 C7 -2.09(18) . . . . ?
N4 C1 C2 C7 179.42(11) . . . . ?
C7 C2 C3 C4 1.71(19) . . . . ?
C1 C2 C3 C4 -177.56(11) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -2.0(2) . . . . ?
C3 C4 C5 C8 176.62(13) . . . . ?
C4 C5 C6 C7 2.1(2) . . . . ?
C8 C5 C6 C7 -176.59(13) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C3 C2 C7 C6 -1.68(19) . . . . ?
C1 C2 C7 C6 177.61(11) . . . . ?
F4 F1 C8 F5 74.8(8) . . . . ?
F6 F1 C8 F5 -84.7(6) . . . . ?
F6 F1 C8 F4 -159.5(6) . . . . ?
F4 F1 C8 F3 129.7(5) . . . . ?
F6 F1 C8 F3 -29.8(4) . . . . ?
F4 F1 C8 F6 159.5(6) . . . . ?
F4 F1 C8 F2 22.6(5) . . . . ?
F6 F1 C8 F2 -136.9(3) . . . . ?
F4 F1 C8 C5 -99.6(4) . . . . ?
F6 F1 C8 C5 100.9(3) . . . . ?
F3 F5 C8 F1 81.5(7) . . . . ?
F2 F5 C8 F1 -73.9(7) . . . . ?
F3 F5 C8 F4 128.7(4) . . . . ?
F2 F5 C8 F4 -26.8(3) . . . . ?
F2 F5 C8 F3 -155.5(4) . . . . ?
F3 F5 C8 F6 18.0(4) . . . . ?
F2 F5 C8 F6 -137.5(3) . . . . ?
F3 F5 C8 F2 155.5(4) . . . . ?
F3 F5 C8 C5 -104.0(3) . . . . ?
F2 F5 C8 C5 100.5(3) . . . . ?
F2 F4 C8 F1 154.8(6) . . . . ?
F1 F4 C8 F5 -130.5(5) . . . . ?
F2 F4 C8 F5 24.3(3) . . . . ?
F1 F4 C8 F3 -76.0(8) . . . . ?
F2 F4 C8 F3 78.8(7) . . . . ?
F1 F4 C8 F6 -18.2(5) . . . . ?
F2 F4 C8 F6 136.7(3) . . . . ?
F1 F4 C8 F2 -154.8(6) . . . . ?
F1 F4 C8 C5 102.6(5) . . . . ?
F2 F4 C8 C5 -102.6(3) . . . . ?
F5 F3 C8 F1 -128.6(4) . . . . ?
F6 F3 C8 F1 30.7(4) . . . . ?
F6 F3 C8 F5 159.3(4) . . . . ?
F5 F3 C8 F4 -80.9(7) . . . . ?
F6 F3 C8 F4 78.4(6) . . . . ?
F5 F3 C8 F6 -159.3(4) . . . . ?
F5 F3 C8 F2 -19.8(4) . . . . ?
F6 F3 C8 F2 139.6(3) . . . . ?
F5 F3 C8 C5 100.5(3) . . . . ?
F6 F3 C8 C5 -100.2(3) . . . . ?
F3 F6 C8 F1 -146.1(4) . . . . ?
F3 F6 C8 F5 -16.7(3) . . . . ?
F1 F6 C8 F5 129.4(4) . . . . ?
F3 F6 C8 F4 -131.1(4) . . . . ?
F1 F6 C8 F4 15.0(4) . . . . ?
F1 F6 C8 F3 146.1(4) . . . . ?
F3 F6 C8 F2 -69.1(6) . . . . ?
F1 F6 C8 F2 77.0(6) . . . . ?
F3 F6 C8 C5 106.5(3) . . . . ?
F1 F6 C8 C5 -107.5(3) . . . . ?
F5 F2 C8 F1 132.5(4) . . . . ?
F4 F2 C8 F1 -18.3(5) . . . . ?
F4 F2 C8 F5 -150.8(4) . . . . ?
F5 F2 C8 F4 150.8(4) . . . . ?
F5 F2 C8 F3 19.3(4) . . . . ?
F4 F2 C8 F3 -131.6(4) . . . . ?
F5 F2 C8 F6 72.4(6) . . . . ?
F4 F2 C8 F6 -78.4(6) . . . . ?
F5 F2 C8 C5 -103.1(3) . . . . ?
F4 F2 C8 C5 106.1(3) . . . . ?
C4 C5 C8 F1 75.8(8) . . . . ?
C6 C5 C8 F1 -105.5(8) . . . . ?
C4 C5 C8 F5 -99.6(5) . . . . ?
C6 C5 C8 F5 79.1(6) . . . . ?
C4 C5 C8 F4 25.1(5) . . . . ?
C6 C5 C8 F4 -156.2(5) . . . . ?
C4 C5 C8 F3 -156.0(7) . . . . ?
C6 C5 C8 F3 22.6(7) . . . . ?
C4 C5 C8 F6 141.4(4) . . . . ?
C6 C5 C8 F6 -39.9(4) . . . . ?
C4 C5 C8 F2 -41.9(6) . . . . ?
C6 C5 C8 F2 136.8(6) . . . . ?

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
N4 H1 N1 . . 4_576 2.7976(17) 0.961(19) 1.837(19) 176.8(14) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5-(4-trifluoromethylphenyl)-1H-tetrazole
_chemical_name_common            TFPHTZ
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PHTZ
_database_code_depnum_ccdc_archive 'CCDC 2226490'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C7 H6 N4'
_chemical_formula_moiety         'C7 H6 N4'
_chemical_formula_weight         146.15
_chemical_melting_point          ?
_chemical_absolute_configuration .

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)
;
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'A m a 2'
_space_group_name_Hall           'A 2 -2a'
_space_group_IT_number           40
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,+Z
3 1/2-X,+Y,+Z
4 1/2+X,-Y,+Z
5 +X,1/2+Y,1/2+Z
6 -X,1/2-Y,1/2+Z
7 1/2-X,1/2+Y,1/2+Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.8121(7)
_cell_length_b                   15.2562(14)
_cell_length_c                   4.5459(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     680.50(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1124
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      29.10
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.459
_exptl_crystal_size_min          0.122
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304.00
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            2102
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.670
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             756
_reflns_number_gt                668
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.622
_reflns_Friedel_fraction_max     0.801
_reflns_Friedel_fraction_full    0.829

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0709
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         756
_refine_ls_number_parameters     60
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0386P)²+0.0808P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(4)
_refine_ls_abs_structure_details 
;
 Flack x determined using 225 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.14135(14) -0.01804(10) -0.1314(4) 0.0433(4) Uani 1 1 d . . . . .
N2 N 0.18436(14) -0.07962(9) -0.3239(4) 0.0480(5) Uani 1 1 d . . . . .
C1 C 0.250000 0.02018(16) -0.0123(5) 0.0342(6) Uani 1 2 d S T P . .
C2 C 0.250000 0.09126(16) 0.2020(6) 0.0382(6) Uani 1 2 d S T P . .
C3 C 0.12813(18) 0.12596(13) 0.3057(4) 0.0484(5) Uani 1 1 d . . . . .
H2 H 0.045676 0.103350 0.239181 0.058 Uiso 1 1 calc R U . . .
C4 C 0.1288(2) 0.19328(13) 0.5052(5) 0.0603(6) Uani 1 1 d . . . . .
H3 H 0.046709 0.215966 0.573771 0.072 Uiso 1 1 calc R U . . .
C5 C 0.250000 0.22752(19) 0.6048(8) 0.0614(8) Uani 1 2 d S T P . .
H4 H 0.249999 0.273580 0.738818 0.074 Uiso 1 2 calc R U P . .
H1 H 0.055(4) -0.007(3) -0.105(10) 0.050(11) Uiso 0.5 1 d . . P . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.3302(19) . ?
N1 N2 1.352(2) . ?
N1 H1 0.87(3) . ?
N2 N2 1.288(3) 3 ?
C1 C2 1.458(3) . ?
C2 C3 1.390(2) . ?
C2 C3 1.390(2) 3 ?
C3 C4 1.370(3) . ?
C3 H2 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H3 0.9300 . ?
C5 H4 0.9300 . ?

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 108.54(14) . . ?
C1 N1 H1 130(3) . . ?
N2 N1 H1 121(3) . . ?
N2 N2 N1 108.20(8) 3 . ?
N1 C1 N1 106.5(2) . 3 ?
N1 C1 C2 126.73(10) . . ?
N1 C1 C2 126.73(10) 3 . ?
C3 C2 C3 118.7(2) . 3 ?
C3 C2 C1 120.66(12) . . ?
C3 C2 C1 120.66(12) 3 . ?
C4 C3 C2 120.40(19) . . ?
C4 C3 H2 119.8 . . ?
C2 C3 H2 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H3 119.8 . . ?
C5 C4 H3 119.8 . . ?
C4 C5 C4 119.7(3) 3 . ?
C4 C5 H4 120.2 3 . ?
C4 C5 H4 120.2 . . ?

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 N2 0.06(16) . . . 3 ?
N2 N1 C1 N1 -0.1(3) . . . 3 ?
N2 N1 C1 C2 178.7(2) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
N1 C1 C2 C3 179.1(2) 3 . . . ?
N1 C1 C2 C3 -179.1(2) . . . 3 ?
N1 C1 C2 C3 -0.5(3) 3 . . 3 ?
C3 C2 C3 C4 0.3(4) 3 . . . ?
C1 C2 C3 C4 -179.4(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C4 -0.6(5) . . . 3 ?

#==============================================================================
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 . . 2_555 2.828(2) 0.87(4) 1.97(4) 169(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5-phenyl-1H-tetrazole
_chemical_name_common            PHTZ
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       antiferroelectric-like
