#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/86/2228682.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_2228682
loop_
_publ_author_name
'Rieth, Thorsten'
'Schollmeyer, Dieter'
'Detert, Heiner'
_publ_section_title
;
 5-Pentyl-1H-tetrazole
;
_journal_coeditor_code           BX2337
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o156
_journal_paper_doi               10.1107/S1600536810052244
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H12 N4'
_chemical_formula_moiety         'C6 H12 N4'
_chemical_formula_sum            'C6 H12 N4'
_chemical_formula_weight         140.20
_chemical_melting_point          315
_chemical_name_systematic
;
5-pentyl-1H-tetrazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.136(10)
_cell_angle_beta                 112.059(9)
_cell_angle_gamma                116.389(7)
_cell_formula_units_Z            4
_cell_length_a                   8.7812(14)
_cell_length_b                   9.6770(12)
_cell_length_c                   11.614(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      69
_cell_measurement_theta_min      65
_cell_volume                     789.6(2)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CORINC (Dräger & Gattow, 1971)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3182
_diffrn_reflns_theta_full        69.95
_diffrn_reflns_theta_max         69.95
_diffrn_reflns_theta_min         4.26
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.200
_refine_ls_extinction_coef       0.0088(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0395
_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)+(0.0611P)²+0.1618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1071
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                2764
_reflns_number_total             2991
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2337.cif
_cod_data_source_block           I
_cod_database_code               2228682
_cod_database_fobs_code          2228682
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
N N1A 0.76292(14) 0.44445(11) 0.33040(10) 0.0321(2) Uani d . 1 . .
H H1A 0.7628 0.5432 0.3397 0.038 Uiso d R 1 . .
N N2A 0.77322(17) 0.38035(13) 0.22933(10) 0.0392(3) Uani d . 1 . .
N N3A 0.77338(17) 0.25012(13) 0.24908(11) 0.0413(3) Uani d . 1 . .
N N4A 0.76329(16) 0.22891(12) 0.36157(10) 0.0358(3) Uani d . 1 . .
C C5A 0.75588(16) 0.35102(13) 0.41070(11) 0.0286(3) Uani d . 1 . .
C C6A 0.74035(18) 0.38071(13) 0.53191(11) 0.0321(3) Uani d . 1 . .
H H6A 0.6195 0.3797 0.5105 0.039 Uiso calc R 1 . .
H H6B 0.8458 0.4884 0.5875 0.039 Uiso calc R 1 . .
C C7A 0.74667(18) 0.25697(14) 0.60683(12) 0.0336(3) Uani d . 1 . .
H H7A 0.6359 0.1501 0.5540 0.040 Uiso calc R 1 . .
H H7B 0.8633 0.2525 0.6233 0.040 Uiso calc R 1 . .
C C8A 0.74449(18) 0.29643(15) 0.73469(12) 0.0360(3) Uani d . 1 . .
H H8A 0.6351 0.3123 0.7186 0.043 Uiso calc R 1 . .
H H8B 0.8619 0.3983 0.7905 0.043 Uiso calc R 1 . .
C C9A 0.7308(2) 0.16675(18) 0.80548(14) 0.0441(3) Uani d . 1 . .
H H9A 0.6116 0.0655 0.7507 0.053 Uiso calc R 1 . .
H H9B 0.8383 0.1489 0.8197 0.053 Uiso calc R 1 . .
C C10A 0.7338(3) 0.2091(2) 0.93461(16) 0.0607(4) Uani d . 1 . .
H H10A 0.7183 0.1198 0.9740 0.091 Uiso calc R 1 . .
H H10B 0.6298 0.2299 0.9215 0.091 Uiso calc R 1 . .
H H10C 0.8555 0.3050 0.9916 0.091 Uiso calc R 1 . .
N N1B 0.77122(14) 0.95284(11) 0.40731(9) 0.0305(2) Uani d . 1 . .
H H1B 0.7639 1.0469 0.3995 0.037 Uiso d R 1 . .
N N2B 0.74619(15) 0.88499(12) 0.50153(10) 0.0350(3) Uani d . 1 . .
N N3B 0.74529(16) 0.75189(12) 0.47932(10) 0.0364(3) Uani d . 1 . .
N N4B 0.76875(15) 0.73261(12) 0.37130(10) 0.0336(2) Uani d . 1 . .
C C5B 0.78464(16) 0.85919(13) 0.32751(11) 0.0288(3) Uani d . 1 . .
C C6B 0.81748(19) 0.89627(13) 0.21354(12) 0.0359(3) Uani d . 1 . .
H H6C 0.9558 0.9640 0.2423 0.043 Uiso calc R 1 . .
H H6D 0.7569 0.9590 0.1766 0.043 Uiso calc R 1 . .
C C7B 0.74053(18) 0.74860(13) 0.10847(11) 0.0326(3) Uani d . 1 . .
H H7C 0.8051 0.6880 0.1436 0.039 Uiso calc R 1 . .
H H7D 0.6030 0.6784 0.0813 0.039 Uiso calc R 1 . .
C C8B 0.77032(18) 0.79245(14) -0.00809(11) 0.0341(3) Uani d . 1 . .
H H8C 0.7002 0.8484 -0.0453 0.041 Uiso calc R 1 . .
H H8D 0.9071 0.8678 0.0205 0.041 Uiso calc R 1 . .
C C9B 0.70495(19) 0.64908(15) -0.11205(12) 0.0380(3) Uani d . 1 . .
H H9C 0.5680 0.5737 -0.1411 0.046 Uiso calc R 1 . .
H H9D 0.7749 0.5930 -0.0751 0.046 Uiso calc R 1 . .
C C10B 0.7361(2) 0.69521(18) -0.22777(13) 0.0501(4) Uani d . 1 . .
H H10D 0.6736 0.5983 -0.2974 0.075 Uiso calc R 1 . .
H H10E 0.8727 0.7536 -0.2030 0.075 Uiso calc R 1 . .
H H10F 0.6822 0.7635 -0.2575 0.075 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5A N1A N2A . . 109.67(9) ?
C5A N1A H1A . . 127.6 ?
N2A N1A H1A . . 122.7 ?
N3A N2A N1A . . 106.07(10) ?
N2A N3A N4A . . 110.18(10) ?
C5A N4A N3A . . 106.84(9) ?
N4A C5A N1A . . 107.23(10) ?
N4A C5A C6A . . 127.37(10) ?
N1A C5A C6A . . 125.40(10) ?
C5A C6A C7A . . 112.98(9) ?
C5A C6A H6A . . 109.0 ?
C7A C6A H6A . . 109.0 ?
C5A C6A H6B . . 109.0 ?
C7A C6A H6B . . 109.0 ?
H6A C6A H6B . . 107.8 ?
C8A C7A C6A . . 111.95(10) ?
C8A C7A H7A . . 109.2 ?
C6A C7A H7A . . 109.2 ?
C8A C7A H7B . . 109.2 ?
C6A C7A H7B . . 109.2 ?
H7A C7A H7B . . 107.9 ?
C7A C8A C9A . . 113.17(11) ?
C7A C8A H8A . . 108.9 ?
C9A C8A H8A . . 108.9 ?
C7A C8A H8B . . 108.9 ?
C9A C8A H8B . . 108.9 ?
H8A C8A H8B . . 107.8 ?
C10A C9A C8A . . 112.79(12) ?
C10A C9A H9A . . 109.0 ?
C8A C9A H9A . . 109.0 ?
C10A C9A H9B . . 109.0 ?
C8A C9A H9B . . 109.0 ?
H9A C9A H9B . . 107.8 ?
C9A C10A H10A . . 109.5 ?
C9A C10A H10B . . 109.5 ?
H10A C10A H10B . . 109.5 ?
C9A C10A H10C . . 109.5 ?
H10A C10A H10C . . 109.5 ?
H10B C10A H10C . . 109.5 ?
C5B N1B N2B . . 109.65(9) ?
C5B N1B H1B . . 129.2 ?
N2B N1B H1B . . 120.8 ?
N3B N2B N1B . . 106.22(9) ?
N2B N3B N4B . . 110.06(9) ?
C5B N4B N3B . . 106.84(9) ?
N4B C5B N1B . . 107.23(10) ?
N4B C5B C6B . . 127.50(10) ?
N1B C5B C6B . . 125.25(10) ?
C5B C6B C7B . . 113.84(9) ?
C5B C6B H6C . . 108.8 ?
C7B C6B H6C . . 108.8 ?
C5B C6B H6D . . 108.8 ?
C7B C6B H6D . . 108.8 ?
H6C C6B H6D . . 107.7 ?
C8B C7B C6B . . 111.84(10) ?
C8B C7B H7C . . 109.2 ?
C6B C7B H7C . . 109.2 ?
C8B C7B H7D . . 109.2 ?
C6B C7B H7D . . 109.2 ?
H7C C7B H7D . . 107.9 ?
C9B C8B C7B . . 113.44(10) ?
C9B C8B H8C . . 108.9 ?
C7B C8B H8C . . 108.9 ?
C9B C8B H8D . . 108.9 ?
C7B C8B H8D . . 108.9 ?
H8C C8B H8D . . 107.7 ?
C8B C9B C10B . . 112.71(11) ?
C8B C9B H9C . . 109.0 ?
C10B C9B H9C . . 109.0 ?
C8B C9B H9D . . 109.0 ?
C10B C9B H9D . . 109.0 ?
H9C C9B H9D . . 107.8 ?
C9B C10B H10D . . 109.5 ?
C9B C10B H10E . . 109.5 ?
H10D C10B H10E . . 109.5 ?
C9B C10B H10F . . 109.5 ?
H10D C10B H10F . . 109.5 ?
H10E C10B H10F . . 109.5 ?
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
N1A C5A . 1.3330(15) ?
N1A N2A . 1.3494(14) ?
N1A H1A . 0.9564 ?
N2A N3A . 1.2937(14) ?
N3A N4A . 1.3628(15) ?
N4A C5A . 1.3223(14) ?
C5A C6A . 1.4892(16) ?
C6A C7A . 1.5267(16) ?
C6A H6A . 0.9900 ?
C6A H6B . 0.9900 ?
C7A C8A . 1.5222(16) ?
C7A H7A . 0.9900 ?
C7A H7B . 0.9900 ?
C8A C9A . 1.5226(18) ?
C8A H8A . 0.9900 ?
C8A H8B . 0.9900 ?
C9A C10A . 1.520(2) ?
C9A H9A . 0.9900 ?
C9A H9B . 0.9900 ?
C10A H10A . 0.9800 ?
C10A H10B . 0.9800 ?
C10A H10C . 0.9800 ?
N1B C5B . 1.3339(15) ?
N1B N2B . 1.3446(14) ?
N1B H1B . 0.9474 ?
N2B N3B . 1.2956(14) ?
N3B N4B . 1.3616(14) ?
N4B C5B . 1.3222(14) ?
C5B C6B . 1.4868(16) ?
C6B C7B . 1.5228(16) ?
C6B H6C . 0.9900 ?
C6B H6D . 0.9900 ?
C7B C8B . 1.5203(16) ?
C7B H7C . 0.9900 ?
C7B H7D . 0.9900 ?
C8B C9B . 1.5167(17) ?
C8B H8C . 0.9900 ?
C8B H8D . 0.9900 ?
C9B C10B . 1.5212(17) ?
C9B H9C . 0.9900 ?
C9B H9D . 0.9900 ?
C10B H10D . 0.9800 ?
C10B H10E . 0.9800 ?
C10B H10F . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1A H1A N4B . 0.96 1.82 2.7773(14) 175
N1B H1B N4A 1_565 0.95 1.84 2.7779(14) 170
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5A N1A N2A N3A . . . . -0.33(14) ?
N1A N2A N3A N4A . . . . 0.02(14) ?
N2A N3A N4A C5A . . . . 0.30(15) ?
N3A N4A C5A N1A . . . . -0.49(13) ?
N3A N4A C5A C6A . . . . 178.87(11) ?
N2A N1A C5A N4A . . . . 0.52(14) ?
N2A N1A C5A C6A . . . . -178.86(11) ?
N4A C5A C6A C7A . . . . 3.98(18) ?
N1A C5A C6A C7A . . . . -176.77(11) ?
C5A C6A C7A C8A . . . . 176.01(10) ?
C6A C7A C8A C9A . . . . 174.26(11) ?
C7A C8A C9A C10A . . . . 178.51(12) ?
C5B N1B N2B N3B . . . . 0.27(13) ?
N1B N2B N3B N4B . . . . -0.24(13) ?
N2B N3B N4B C5B . . . . 0.13(14) ?
N3B N4B C5B N1B . . . . 0.04(13) ?
N3B N4B C5B C6B . . . . 178.27(11) ?
N2B N1B C5B N4B . . . . -0.19(13) ?
N2B N1B C5B C6B . . . . -178.47(11) ?
N4B C5B C6B C7B . . . . 28.32(18) ?
N1B C5B C6B C7B . . . . -153.76(12) ?
C5B C6B C7B C8B . . . . 177.66(10) ?
C6B C7B C8B C9B . . . . 176.94(11) ?
C7B C8B C9B C10B . . . . -179.91(11) ?
