#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/87/7208789.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7208789
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Deadman, John J.'
'Palmer, Rex A.'
'Male, Louise'
'Coles, Simon J.'
'Uzoh, Ogaga G.'
'Price, Sarah L.'
_publ_section_title
;
 The unexpected but predictable tetrazole packing in flexible
 1-benzyl-1H-tetrazole
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              6441
_journal_paper_doi               10.1039/c2ce25940k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety
;
C8 H8 N4
;
_chemical_formula_sum            'C8 H8 N4'
_chemical_formula_weight         160.18
_chemical_melting_point          ?
_chemical_name_common            '1-H-Tetrazole, 1-(Phenylmethyl)'
_chemical_name_systematic
;
1-H-Tetrazole, 1-(Phenylmethyl)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.949(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.6843(5)
_cell_length_b                   5.5794(4)
_cell_length_c                   9.4459(7)
_cell_measurement_reflns_used    5624
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.14
_cell_volume                     397.61(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'MERCURY (Bruno et al 2002)'
_computing_publication_material  SHELX97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX-S (Sheldrick, 1986)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  BrukerNoniusRoperCCDcameraonκ-goniostat
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5629
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sheldrick, G. M. SADABS 2007/2'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Shard
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1718
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0149P)²+0.0804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0870
_reflns_number_gt                822
_reflns_number_total             977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25940k.txt
_cod_data_source_block
1-H-Tetrazole,1-(Phenylmethyl)_(2008src0576_CCDC804779)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not
given.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7208789
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C7 C 0.3268(2) 0.0713(4) 0.1234(2) 0.0233(4) Uani 1 1 d .
C8 C 0.3471(3) 0.2524(4) 0.0268(2) 0.0262(4) Uani 1 1 d .
H8 H 0.4191 0.3873 0.0591 0.031 Uiso 1 1 calc R
C9 C 0.2632(3) 0.2376(4) -0.1158(2) 0.0295(5) Uani 1 1 d .
H9 H 0.2779 0.3620 -0.1812 0.035 Uiso 1 1 calc R
C10 C 0.1576(3) 0.0415(4) -0.1637(2) 0.0314(5) Uani 1 1 d .
H10 H 0.1001 0.0316 -0.2619 0.038 Uiso 1 1 calc R
C11 C 0.1357(3) -0.1402(5) -0.0686(2) 0.0312(5) Uani 1 1 d .
H11 H 0.0633 -0.2747 -0.1012 0.037 Uiso 1 1 calc R
C12 C 0.2199(2) -0.1242(4) 0.0742(2) 0.0273(4) Uani 1 1 d .
H12 H 0.2045 -0.2484 0.1395 0.033 Uiso 1 1 calc R
C6 C 0.4204(3) 0.0846(4) 0.2787(2) 0.0278(5) Uani 1 1 d .
H6A H 0.4326 -0.0791 0.3198 0.033 Uiso 1 1 calc R
H6B H 0.5410 0.1503 0.2830 0.033 Uiso 1 1 calc R
C5 C 0.1996(3) 0.1792(4) 0.4413(2) 0.0305(5) Uani 1 1 d .
N1 N 0.3248(2) 0.2356(3) 0.36642(17) 0.0245(4) Uani 1 1 d .
N2 N 0.3505(2) 0.4736(3) 0.3762(2) 0.0300(4) Uani 1 1 d .
N3 N 0.2432(2) 0.5566(4) 0.45558(18) 0.0303(4) Uani 1 1 d .
N4 N 0.1461(2) 0.3741(4) 0.49835(18) 0.0315(4) Uani 1 1 d .
H5 H 0.162(3) 0.029(4) 0.453(2) 0.034(6) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C7 0.0224(9) 0.0248(10) 0.0234(10) -0.0002(9) 0.0064(8) 0.0036(9)
C8 0.0252(10) 0.0249(10) 0.0297(12) -0.0003(9) 0.0085(9) -0.0008(9)
C9 0.0332(11) 0.0283(11) 0.0291(12) 0.0049(9) 0.0115(9) 0.0010(10)
C10 0.0298(11) 0.0404(13) 0.0228(11) -0.0017(10) 0.0020(9) 0.0029(10)
C11 0.0272(10) 0.0280(10) 0.0368(12) -0.0026(11) 0.0019(9) -0.0011(10)
C12 0.0279(10) 0.0237(10) 0.0315(11) 0.0028(11) 0.0090(9) 0.0001(10)
C6 0.0276(11) 0.0272(11) 0.0290(12) -0.0005(9) 0.0059(9) 0.0028(9)
C5 0.0370(13) 0.0272(12) 0.0293(13) 0.0021(10) 0.0115(10) -0.0027(10)
N1 0.0296(9) 0.0239(9) 0.0192(9) -0.0009(8) 0.0025(7) -0.0004(8)
N2 0.0331(10) 0.0228(9) 0.0334(11) -0.0012(8) 0.0051(9) -0.0023(7)
N3 0.0351(10) 0.0282(9) 0.0261(9) 0.0006(8) 0.0025(8) 0.0032(8)
N4 0.0348(9) 0.0297(9) 0.0302(10) -0.0006(9) 0.0068(8) 0.0004(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 C7 C12 118.89(18)
C8 C7 C6 120.73(18)
C12 C7 C6 120.38(18)
C9 C8 C7 120.48(19)
C9 C8 H8 119.8
C7 C8 H8 119.8
C8 C9 C10 120.12(19)
C8 C9 H9 119.9
C10 C9 H9 119.9
C9 C10 C11 120.07(19)
C9 C10 H10 120.0
C11 C10 H10 120.0
C12 C11 C10 119.6(2)
C12 C11 H11 120.2
C10 C11 H11 120.2
C11 C12 C7 120.9(2)
C11 C12 H12 119.6
C7 C12 H12 119.6
N1 C6 C7 112.26(16)
N1 C6 H6A 109.2
C7 C6 H6A 109.2
N1 C6 H6B 109.2
C7 C6 H6B 109.2
H6A C6 H6B 107.9
N4 C5 N1 109.6(2)
N4 C5 H5 126.0(14)
N1 C5 H5 124.4(14)
C5 N1 N2 107.95(18)
C5 N1 C6 130.53(18)
N2 N1 C6 121.45(17)
N3 N2 N1 106.89(17)
N2 N3 N4 110.24(18)
C5 N4 N3 105.34(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C7 C8 1.390(3)
C7 C12 1.392(3)
C7 C6 1.508(3)
C8 C9 1.381(3)
C8 H8 0.9500
C9 C10 1.386(3)
C9 H9 0.9500
C10 C11 1.386(3)
C10 H10 0.9500
C11 C12 1.383(3)
C11 H11 0.9500
C12 H12 0.9500
C6 N1 1.472(2)
C6 H6A 0.9900
C6 H6B 0.9900
C5 N4 1.314(3)
C5 N1 1.336(3)
C5 H5 0.90(2)
N1 N2 1.343(2)
N2 N3 1.301(2)
N3 N4 1.368(3)
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
C12 C7 C8 C9 -0.4(3)
C6 C7 C8 C9 179.02(18)
C7 C8 C9 C10 0.1(3)
C8 C9 C10 C11 0.1(3)
C9 C10 C11 C12 0.0(3)
C10 C11 C12 C7 -0.2(3)
C8 C7 C12 C11 0.4(3)
C6 C7 C12 C11 -178.95(18)
C8 C7 C6 N1 82.1(2)
C12 C7 C6 N1 -98.6(2)
N4 C5 N1 N2 -0.3(2)
N4 C5 N1 C6 -177.20(18)
C7 C6 N1 C5 89.9(3)
C7 C6 N1 N2 -86.7(2)
C5 N1 N2 N3 0.2(2)
C6 N1 N2 N3 177.48(16)
N1 N2 N3 N4 -0.1(2)
N1 C5 N4 N3 0.2(2)
N2 N3 N4 C5 -0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 3822426
