data_2013906
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o293
_journal_page_last  o294
_publ_section_title
;
1-Phenyl-5-(piperidinomethyl)-1H-tetrazole
;
loop_
_publ_author_name
  'Lyakhov, Alexander S.'
  'Voitekhovich, Sergei V.'
  'Gaponik, Pavel N.'
  'Ivashkevich, Ludmila S.'
_chemical_formula_moiety  'C13 H17 N5'
_chemical_formula_sum  'C13 H17 N5'
_chemical_formula_iupac  'C13 H17 N5'
_chemical_formula_weight  243.32
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  7.7537(13)
_cell_length_b  10.436(3)
_cell_length_c  15.937(3)
_cell_angle_alpha  90.00
_cell_angle_beta  96.142(13)
_cell_angle_gamma  90.00
_cell_volume  1282.2(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.260
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  N1 0.33395(12) 0.14877(8) 0.53722(5) 0.0455(2) Uani d . 1 . . N
  N2 0.23195(15) 0.13018(10) 0.46377(6) 0.0598(3) Uani d . 1 . . N
  N3 0.33297(18) 0.13906(11) 0.40455(6) 0.0697(3) Uani d . 1 . . N
  N4 0.49897(16) 0.16229(10) 0.43672(6) 0.0632(3) Uani d . 1 . . N
  C5 0.49825(15) 0.16835(9) 0.51921(7) 0.0482(3) Uani d . 1 . . C
  C6 0.26254(13) 0.13607(9) 0.61587(6) 0.0433(2) Uani d . 1 . . C
  C7 0.14675(15) 0.03748(11) 0.62453(8) 0.0513(3) Uani d . 1 . . C
  H7 0.1197(17) -0.0218(14) 0.5794(8) 0.063(4) Uiso d . 1 . . H
  C8 0.07734(16) 0.02440(12) 0.70039(8) 0.0589(3) Uani d . 1 . . C
  H8 -0.006(2) -0.0446(16) 0.7068(9) 0.077(4) Uiso d . 1 . . H
  C9 0.12399(16) 0.10749(14) 0.76591(8) 0.0610(3) Uani d . 1 . . C
  H9 0.0770(19) 0.0923(15) 0.8186(9) 0.078(4) Uiso d . 1 . . H
  C10 0.23807(16) 0.20551(14) 0.75615(7) 0.0588(3) Uani d . 1 . . C
  H10 0.267(2) 0.2671(17) 0.8010(10) 0.086(5) Uiso d . 1 . . H
  C11 0.30840(14) 0.22187(11) 0.68054(7) 0.0502(3) Uani d . 1 . . C
  H11 0.3870(18) 0.2920(13) 0.6702(8) 0.060(3) Uiso d . 1 . . H
  C12 0.65236(15) 0.19014(11) 0.58159(7) 0.0508(3) Uani d . 1 . . C
  H12A 0.6346(16) 0.1446(12) 0.6349(8) 0.053(3) Uiso d . 1 . . H
  H12B 0.7549(18) 0.1512(13) 0.5579(8) 0.063(4) Uiso d . 1 . . H
  N13 0.68014(11) 0.32565(8) 0.60180(5) 0.0441(2) Uani d . 1 . . N
  C14 0.73631(16) 0.39423(11) 0.52936(7) 0.0519(3) Uani d . 1 . . C
  H14A 0.6458(19) 0.3857(13) 0.4823(8) 0.064(4) Uiso d . 1 . . H
  H14B 0.849(2) 0.3515(14) 0.5120(9) 0.070(4) Uiso d . 1 . . H
  C15 0.76814(18) 0.53468(12) 0.54975(9) 0.0615(3) Uani d . 1 . . C
  H15A 0.8020(19) 0.5799(15) 0.4980(10) 0.076(4) Uiso d . 1 . . H
  H15B 0.657(2) 0.5723(15) 0.5626(9) 0.071(4) Uiso d . 1 . . H
  C16 0.90389(17) 0.55095(14) 0.62460(9) 0.0633(3) Uani d . 1 . . C
  H16A 1.017(2) 0.5169(15) 0.6112(9) 0.075(4) Uiso d . 1 . . H
  H16B 0.916(2) 0.6458(16) 0.6392(11) 0.087(5) Uiso d . 1 . . H
  C17 0.85428(18) 0.47332(14) 0.69841(8) 0.0622(3) Uani d . 1 . . C
  H17A 0.952(2) 0.4698(15) 0.7459(9) 0.076(4) Uiso d . 1 . . H
  H17B 0.749(2) 0.5138(15) 0.7203(9) 0.074(4) Uiso d . 1 . . H
  C18 0.81532(16) 0.33599(13) 0.67374(8) 0.0558(3) Uani d . 1 . . C
  H18A 0.927(2) 0.2922(14) 0.6587(9) 0.073(4) Uiso d . 1 . . H
  H18B 0.7723(17) 0.2852(14) 0.7186(9) 0.067(4) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  N1 0.0559(5) 0.0387(4) 0.0416(4) -0.0051(4) 0.0036(4) -0.0012(3)
  N2 0.0790(7) 0.0532(5) 0.0451(5) -0.0160(5) -0.0034(5) -0.0049(4)
  N3 0.1051(9) 0.0591(6) 0.0450(5) -0.0183(6) 0.0086(5) -0.0077(4)
  N4 0.0893(8) 0.0526(6) 0.0506(5) -0.0091(5) 0.0208(5) -0.0066(4)
  C5 0.0622(6) 0.0353(5) 0.0492(5) -0.0007(4) 0.0150(5) 0.0003(4)
  C6 0.0446(5) 0.0417(5) 0.0434(5) 0.0028(4) 0.0036(4) 0.0014(4)
  C7 0.0528(6) 0.0427(5) 0.0589(6) -0.0021(4) 0.0085(5) -0.0009(5)
  C8 0.0524(6) 0.0566(7) 0.0698(7) 0.0006(5) 0.0163(5) 0.0103(6)
  C9 0.0528(6) 0.0796(9) 0.0519(6) 0.0087(6) 0.0115(5) 0.0098(6)
  C10 0.0528(6) 0.0760(8) 0.0468(6) 0.0031(6) 0.0019(5) -0.0080(5)
  C11 0.0477(5) 0.0533(6) 0.0491(6) -0.0027(5) 0.0023(4) -0.0052(4)
  C12 0.0505(6) 0.0444(5) 0.0588(6) 0.0049(4) 0.0115(5) 0.0085(5)
  N13 0.0395(4) 0.0463(5) 0.0469(4) 0.0018(3) 0.0073(3) 0.0066(3)
  C14 0.0538(6) 0.0542(6) 0.0475(6) -0.0066(5) 0.0043(5) 0.0086(4)
  C15 0.0617(7) 0.0532(6) 0.0679(7) -0.0081(5) -0.0010(6) 0.0115(6)
  C16 0.0524(7) 0.0644(8) 0.0723(8) -0.0101(6) 0.0033(6) -0.0018(6)
  C17 0.0549(7) 0.0765(9) 0.0549(7) -0.0032(6) 0.0045(5) -0.0068(6)
  C18 0.0522(6) 0.0669(7) 0.0477(6) 0.0028(5) 0.0023(5) 0.0097(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  N1 C5 . 1.3510(15) yes
  N1 N2 . 1.3546(12) yes
  N1 C6 . 1.4296(13) yes
  N2 N3 . 1.2928(15) yes
  N3 N4 . 1.3553(17) yes
  N4 C5 . 1.3169(14) yes
  C5 C12 . 1.4878(16) yes
  C6 C7 . 1.3821(15) ?
  C6 C11 . 1.3828(15) ?
  C7 C8 . 1.3816(17) ?
  C7 H7 . 0.955(14) ?
  C8 C9 . 1.3757(19) ?
  C8 H8 . 0.981(16) ?
  C9 C10 . 1.372(2) ?
  C9 H9 . 0.963(15) ?
  C10 C11 . 1.3853(16) ?
  C10 H10 . 0.970(17) ?
  C11 H11 . 0.978(14) ?
  C12 N13 . 1.4613(15) yes
  C12 H12A . 0.996(13) ?
  C12 H12B . 1.002(14) ?
  N13 C14 . 1.4637(13) yes
  N13 C18 . 1.4724(14) yes
  C14 C15 . 1.5158(18) yes
  C14 H14A . 0.975(14) ?
  C14 H14B . 1.045(15) ?
  C15 C16 . 1.5136(19) yes
  C15 H15A . 1.010(15) ?
  C15 H15B . 0.987(15) ?
  C16 C17 . 1.5116(19) yes
  C16 H16A . 0.989(16) ?
  C16 H16B . 1.019(17) ?
  C17 C18 . 1.508(2) yes
  C17 H17A . 1.012(16) ?
  C17 H17B . 1.013(15) ?
  C18 H18A . 1.028(16) ?
  C18 H18B . 0.976(14) ?