#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013906.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2013906
loop_
_publ_author_name
'Lyakhov, Alexander S.'
'Voitekhovich, Sergei V.'
'Gaponik, Pavel N.'
'Ivashkevich, Ludmila S.'
_publ_section_title
;
 1-Phenyl-5-(piperidinomethyl)-1H-tetrazole
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o293
_journal_page_last               o294
_journal_paper_doi               10.1107/S0108270104005554
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H17 N5'
_chemical_formula_moiety         'C13 H17 N5'
_chemical_formula_sum            'C13 H17 N5'
_chemical_formula_weight         243.32
_chemical_name_systematic
;
1-Phenyl-5-(piperidinomethyl)-1H-tetrazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.142(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7537(13)
_cell_length_b                   10.436(3)
_cell_length_c                   15.937(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.3
_cell_measurement_theta_min      12.4
_cell_volume                     1282.2(5)
_computing_cell_refinement       'R3m software'
_computing_data_collection       'R3m software (Nicolet, 1980)'
_computing_data_reduction        'R3m software'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 1997) and
PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nicolet R3m four-circle diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4125
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.251
_refine_ls_extinction_coef       0.480(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0421
_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)+(0.0582P)²+0.0879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                2759
_reflns_number_total             3746
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av1171.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2013906
_cod_database_fobs_code          2013906
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'
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_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
C5 N1 N2 108.35(9)
C5 N1 C6 131.51(9)
N2 N1 C6 119.95(9)
N3 N2 N1 106.10(10)
N2 N3 N4 111.21(9)
C5 N4 N3 106.32(10)
N4 C5 N1 108.03(11)
N4 C5 C12 125.84(11)
N1 C5 C12 126.11(10)
C7 C6 C11 121.71(11)
C7 C6 N1 118.24(10)
C11 C6 N1 120.05(9)
C8 C7 C6 118.62(11)
C8 C7 H7 121.4(8)
C6 C7 H7 120.0(8)
C9 C8 C7 120.43(12)
C9 C8 H8 120.4(9)
C7 C8 H8 119.1(9)
C10 C9 C8 120.28(11)
C10 C9 H9 122.0(9)
C8 C9 H9 117.6(10)
C9 C10 C11 120.60(12)
C9 C10 H10 120.9(10)
C11 C10 H10 118.5(10)
C6 C11 C10 118.35(11)
C6 C11 H11 118.4(7)
C10 C11 H11 123.3(7)
N13 C12 C5 112.59(9)
N13 C12 H12A 107.7(7)
C5 C12 H12A 108.8(7)
N13 C12 H12B 111.8(8)
C5 C12 H12B 107.4(8)
H12A C12 H12B 108.4(11)
C12 N13 C14 110.40(9)
C12 N13 C18 108.57(9)
C14 N13 C18 109.35(9)
N13 C14 C15 111.04(10)
N13 C14 H14A 108.2(8)
C15 C14 H14A 109.9(8)
N13 C14 H14B 109.2(8)
C15 C14 H14B 110.3(8)
H14A C14 H14B 108.1(11)
C16 C15 C14 111.17(11)
C16 C15 H15A 111.8(9)
C14 C15 H15A 109.1(9)
C16 C15 H15B 109.9(9)
C14 C15 H15B 107.6(9)
H15A C15 H15B 107.0(12)
C17 C16 C15 109.86(11)
C17 C16 H16A 106.3(9)
C15 C16 H16A 110.3(9)
C17 C16 H16B 111.6(9)
C15 C16 H16B 109.3(10)
H16A C16 H16B 109.4(13)
C18 C17 C16 111.53(11)
C18 C17 H17A 105.9(9)
C16 C17 H17A 111.7(8)
C18 C17 H17B 109.9(9)
C16 C17 H17B 109.1(9)
H17A C17 H17B 108.7(11)
N13 C18 C17 112.25(10)
N13 C18 H18A 109.4(8)
C17 C18 H18A 109.4(8)
N13 C18 H18B 105.0(8)
C17 C18 H18B 113.6(8)
H18A C18 H18B 106.9(12)
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) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C11 H11 N13 0.978(14) 2.648(13) 3.4395(15) 138.3(10)
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
C5 N1 N2 N3 -0.24(12)
C6 N1 N2 N3 -175.69(9)
N1 N2 N3 N4 0.33(13)
N2 N3 N4 C5 -0.30(13)
N3 N4 C5 N1 0.14(12)
N3 N4 C5 C12 178.92(10)
N2 N1 C5 N4 0.06(11)
C6 N1 C5 N4 174.80(10)
N2 N1 C5 C12 -178.73(9)
C6 N1 C5 C12 -3.99(17)
C5 N1 C6 C7 -133.92(11)
N2 N1 C6 C7 40.32(13)
C5 N1 C6 C11 46.70(15)
N2 N1 C6 C11 -139.06(10)
C11 C6 C7 C8 -0.73(17)
N1 C6 C7 C8 179.90(10)
C6 C7 C8 C9 -0.48(18)
C7 C8 C9 C10 0.99(19)
C8 C9 C10 C11 -0.31(19)
C7 C6 C11 C10 1.39(17)
N1 C6 C11 C10 -179.25(10)
C9 C10 C11 C6 -0.86(18)
N4 C5 C12 N13 91.94(13)
N1 C5 C12 N13 -89.49(12)
C5 C12 N13 C14 -69.67(11)
C5 C12 N13 C18 170.48(9)
C12 N13 C14 C15 -179.20(9)
C18 N13 C14 C15 -59.81(12)
N13 C14 C15 C16 58.41(14)
C14 C15 C16 C17 -53.38(16)
C15 C16 C17 C18 51.90(15)
C12 N13 C18 C17 179.29(10)
C14 N13 C18 C17 58.77(13)
C16 C17 C18 N13 -55.59(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107572
