#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/19/2201965.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_2201965
loop_
_publ_author_name
'Dakir, M.'
'Auhmani, A.'
'Akssira, M.'
'Benharref, A.'
'Pierrot, M.'
_publ_section_title
;
 6,6,8-Triméthyl-6,7-dihydro-5H-tétrazolo[1,5-a]azepine
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o643
_journal_page_last               o645
_journal_paper_doi               10.1107/S1600536803007785
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C9 H14 N4'
_chemical_formula_moiety         'C9 H14 N4'
_chemical_formula_sum            'C9 H14 N4'
_chemical_formula_weight         178.24
_chemical_name_systematic        ?
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000
_cell_angle_beta                 92.905(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            12
_cell_length_a                   12.0240(10)
_cell_length_b                   13.6240(10)
_cell_length_c                   18.080(2)
_cell_measurement_reflns_used    18845
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     2958.0(5)
_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       φ
_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  0.14
_diffrn_reflns_av_sigmaI/netI    0.0791
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18845
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0975
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0110P)²+1.9298P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                3440
_reflns_number_total             5516
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6063.cif
_cod_data_source_block           I
_cod_original_cell_volume        2958.0(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201965
_cod_database_fobs_code          2201965
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 0.1612(3) 0.5499(2) -0.01800(16) 0.0623(8) Uani d . 1 . . N
N2 0.2526(3) 0.5871(2) -0.04789(17) 0.0705(9) Uani d . 1 . . N
N3 0.3422(3) 0.5577(2) -0.01115(17) 0.0608(8) Uani d . 1 . . N
N4 0.3076(2) 0.49988(19) 0.04372(15) 0.0506(7) Uani d . 1 . . N
N21 0.4018(2) 0.5333(2) 0.30194(15) 0.0557(8) Uani d . 1 . . N
N22 0.3093(3) 0.5781(2) 0.27291(16) 0.0637(8) Uani d . 1 . . N
N23 0.2247(2) 0.5616(2) 0.31326(16) 0.0577(8) Uani d . 1 . . N
N24 0.2638(2) 0.50424(18) 0.37043(14) 0.0482(7) Uani d . 1 . . N
N41 0.9036(3) 0.4504(2) 0.35568(17) 0.0665(9) Uani d . 1 . . N
N42 0.8128(3) 0.4094(2) 0.38442(17) 0.0708(9) Uani d . 1 . . N
N43 0.7236(3) 0.4309(2) 0.34407(17) 0.0623(8) Uani d . 1 . . N
N44 0.7568(2) 0.48686(19) 0.28775(15) 0.0491(7) Uani d . 1 . . N
C5 0.3883(3) 0.4555(2) 0.09782(18) 0.0529(9) Uani d . 1 . . C
H5A 0.3919 0.4953 0.1423 0.064 Uiso calc R 1 . . H
H5B 0.4614 0.4566 0.0775 0.064 Uiso calc R 1 . . H
C6 0.3608(3) 0.3502(2) 0.11882(17) 0.0477(8) Uani d . 1 . . C
C7 0.2611(3) 0.3459(2) 0.16748(18) 0.0515(9) Uani d . 1 . . C
H7A 0.2542 0.2784 0.1836 0.062 Uiso calc R 1 . . H
H7B 0.2800 0.3845 0.2114 0.062 Uiso calc R 1 . . H
C8 0.1477(3) 0.3783(2) 0.13899(18) 0.0475(8) Uani d . 1 . . C
C9 0.1229(3) 0.4413(2) 0.08425(18) 0.0515(9) Uani d . 1 . . C
H9 0.0474 0.4520 0.0737 0.062 Uiso calc R 1 . . H
C10 0.1971(3) 0.4950(2) 0.03923(17) 0.0413(7) Uani d . 1 . . C
C11 0.0536(3) 0.3333(3) 0.1791(2) 0.0697(11) Uani d . 1 . . C
H11A -0.0162 0.3555 0.1570 0.105 Uiso calc R 1 . . H
H11B 0.0593 0.3526 0.2302 0.105 Uiso calc R 1 . . H
H11C 0.0576 0.2631 0.1757 0.105 Uiso calc R 1 . . H
C12 0.3418(3) 0.2864(3) 0.04976(19) 0.0671(11) Uani d . 1 . . C
H12A 0.3332 0.2191 0.0643 0.101 Uiso calc R 1 . . H
H12B 0.4045 0.2921 0.0192 0.101 Uiso calc R 1 . . H
H12C 0.2757 0.3078 0.0224 0.101 Uiso calc R 1 . . H
C13 0.4627(3) 0.3120(3) 0.1648(2) 0.0755(12) Uani d . 1 . . C
H13A 0.4505 0.2449 0.1784 0.113 Uiso calc R 1 . . H
H13B 0.4739 0.3512 0.2087 0.113 Uiso calc R 1 . . H
H13C 0.5275 0.3161 0.1359 0.113 Uiso calc R 1 . . H
C25 0.1892(3) 0.4740(3) 0.42799(19) 0.0578(9) Uani d . 1 . . C
H25A 0.1128 0.4802 0.4087 0.069 Uiso calc R 1 . . H
H25B 0.1992 0.5182 0.4699 0.069 Uiso calc R 1 . . H
C26 0.2086(3) 0.3689(2) 0.45484(18) 0.0523(9) Uani d . 1 . . C
C27 0.3169(3) 0.3594(3) 0.50148(18) 0.0596(10) Uani d . 1 . . C
H27A 0.3123 0.4045 0.5427 0.071 Uiso calc R 1 . . H
H27B 0.3185 0.2937 0.5222 0.071 Uiso calc R 1 . . H
C28 0.4270(3) 0.3762(2) 0.46899(18) 0.0525(9) Uani d . 1 . . C
C29 0.4482(3) 0.4302(2) 0.40976(18) 0.0514(9) Uani d . 1 . . C
H29 0.5221 0.4314 0.3970 0.062 Uiso calc R 1 . . H
C30 0.3719(2) 0.4870(2) 0.36283(17) 0.0404(7) Uani d . 1 . . C
C31 0.5236(3) 0.3261(3) 0.5100(2) 0.0818(13) Uani d . 1 . . C
H31A 0.5915 0.3429 0.4873 0.123 Uiso calc R 1 . . H
H31B 0.5131 0.2563 0.5080 0.123 Uiso calc R 1 . . H
H31C 0.5276 0.3473 0.5607 0.123 Uiso calc R 1 . . H
C32 0.1118(3) 0.3456(3) 0.5047(2) 0.0844(13) Uani d . 1 . . C
H32A 0.1215 0.2809 0.5250 0.127 Uiso calc R 1 . . H
H32B 0.0426 0.3487 0.4758 0.127 Uiso calc R 1 . . H
H32C 0.1110 0.3926 0.5441 0.127 Uiso calc R 1 . . H
C33 0.2044(3) 0.2965(3) 0.39031(19) 0.0686(11) Uani d . 1 . . C
H33A 0.2108 0.2308 0.4091 0.103 Uiso calc R 1 . . H
H33B 0.2648 0.3097 0.3590 0.103 Uiso calc R 1 . . H
H33C 0.1349 0.3036 0.3622 0.103 Uiso calc R 1 . . H
C45 0.6776(3) 0.5227(2) 0.23030(18) 0.0548(9) Uani d . 1 . . C
H45A 0.6028 0.5153 0.2472 0.066 Uiso calc R 1 . . H
H45B 0.6834 0.4826 0.1864 0.066 Uiso calc R 1 . . H
C46 0.6957(3) 0.6302(2) 0.20960(17) 0.0477(8) Uani d . 1 . . C
C47 0.7980(3) 0.6428(2) 0.16428(17) 0.0512(9) Uani d . 1 . . C
H47A 0.7844 0.6059 0.1189 0.061 Uiso calc R 1 . . H
H47B 0.8011 0.7115 0.1503 0.061 Uiso calc R 1 . . H
C48 0.9120(3) 0.6153(2) 0.19438(18) 0.0485(8) Uani d . 1 . . C
C49 0.9389(3) 0.5542(2) 0.24975(19) 0.0535(9) Uani d . 1 . . C
H49 1.0148 0.5460 0.2606 0.064 Uiso calc R 1 . . H
C50 0.8664(3) 0.4988(2) 0.29532(17) 0.0435(8) Uani d . 1 . . C
C51 1.0048(3) 0.6630(3) 0.1544(2) 0.0734(12) Uani d . 1 . . C
H51A 1.0752 0.6396 0.1746 0.110 Uiso calc R 1 . . H
H51B 1.0010 0.7329 0.1603 0.110 Uiso calc R 1 . . H
H51C 0.9973 0.6469 0.1027 0.110 Uiso calc R 1 . . H
C52 0.7045(3) 0.6950(3) 0.27866(19) 0.0643(10) Uani d . 1 . . C
H52A 0.7064 0.7628 0.2641 0.096 Uiso calc R 1 . . H
H52B 0.7715 0.6792 0.3073 0.096 Uiso calc R 1 . . H
H52C 0.6413 0.6838 0.3079 0.096 Uiso calc R 1 . . H
C53 0.5919(3) 0.6604(3) 0.1614(2) 0.0726(11) Uani d . 1 . . C
H53A 0.5997 0.7272 0.1455 0.109 Uiso calc R 1 . . H
H53B 0.5269 0.6546 0.1898 0.109 Uiso calc R 1 . . H
H53C 0.5845 0.6183 0.1189 0.109 Uiso calc R 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
_geom_angle_publ_flag
C10 N1 N2 106.5(3) y
N3 N2 N1 110.6(3) y
N2 N3 N4 106.1(3) y
C10 N4 N3 109.2(3) y
C10 N4 C5 130.0(3) y
N3 N4 C5 120.8(3) y
C30 N21 N22 106.4(3) y
N23 N22 N21 110.9(3) y
N22 N23 N24 106.0(3) y
C30 N24 N23 108.9(2) y
C30 N24 C25 131.1(3) y
N23 N24 C25 120.0(3) y
C50 N41 N42 106.0(3) y
N43 N42 N41 110.5(3) y
N42 N43 N44 106.5(3) y
C50 N44 N43 108.8(3) y
C50 N44 C45 129.9(3) y
N43 N44 C45 121.4(3) y
N4 C5 C6 114.1(3) ?
C5 C6 C7 111.6(3) ?
C5 C6 C12 110.9(3) ?
C7 C6 C12 111.1(3) ?
C5 C6 C13 106.0(3) ?
C7 C6 C13 107.7(3) ?
C12 C6 C13 109.3(3) ?
C8 C7 C6 121.2(3) ?
C9 C8 C7 127.6(3) ?
C9 C8 C11 118.4(3) ?
C7 C8 C11 114.0(3) ?
C8 C9 C10 128.8(3) ?
N4 C10 N1 107.7(3) ?
N4 C10 C9 129.7(3) ?
N1 C10 C9 122.7(3) ?
N24 C25 C26 113.6(3) ?
C27 C26 C25 111.6(3) ?
C27 C26 C33 111.3(3) ?
C25 C26 C33 111.4(3) ?
C27 C26 C32 108.0(3) ?
C25 C26 C32 105.8(3) ?
C33 C26 C32 108.5(3) ?
C28 C27 C26 121.4(3) ?
C29 C28 C27 127.6(3) ?
C29 C28 C31 118.0(3) ?
C27 C28 C31 114.4(3) ?
C28 C29 C30 128.7(3) ?
N24 C30 N21 107.8(3) ?
N24 C30 C29 128.9(3) ?
N21 C30 C29 123.3(3) ?
N44 C45 C46 113.6(3) ?
C47 C46 C52 110.5(3) ?
C47 C46 C45 111.6(3) ?
C52 C46 C45 111.0(3) ?
C47 C46 C53 108.6(3) ?
C52 C46 C53 109.2(3) ?
C45 C46 C53 105.8(3) ?
C48 C47 C46 121.8(3) ?
C49 C48 C47 127.9(3) ?
C49 C48 C51 118.2(3) ?
C47 C48 C51 113.8(3) ?
C48 C49 C50 128.8(3) ?
N44 C50 N41 108.2(3) ?
N44 C50 C49 129.1(3) ?
N41 C50 C49 122.7(3) ?
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 C10 . 1.331(4) y
N1 N2 . 1.348(4) y
N2 N3 . 1.300(4) y
N3 N4 . 1.349(3) y
N4 C10 . 1.329(4) y
N4 C5 . 1.472(4) y
N21 C30 . 1.334(4) y
N21 N22 . 1.350(4) y
N22 N23 . 1.301(4) y
N23 N24 . 1.360(3) y
N24 C30 . 1.334(4) y
N24 C25 . 1.467(4) y
N41 C50 . 1.333(4) y
N41 N42 . 1.353(4) y
N42 N43 . 1.299(4) y
N43 N44 . 1.348(3) y
N44 C50 . 1.329(4) y
N44 C45 . 1.457(4) y
C5 C6 . 1.524(4) ?
C6 C7 . 1.524(4) ?
C6 C12 . 1.530(4) ?
C6 C13 . 1.536(4) ?
C7 C8 . 1.499(4) ?
C8 C9 . 1.332(4) ?
C8 C11 . 1.505(4) ?
C9 C10 . 1.437(4) ?
C25 C26 . 1.526(4) ?
C26 C27 . 1.521(5) ?
C26 C33 . 1.526(5) ?
C26 C32 . 1.540(4) ?
C27 C28 . 1.493(5) ?
C28 C29 . 1.334(4) ?
C28 C31 . 1.509(4) ?
C29 C30 . 1.443(4) ?
C45 C46 . 1.530(4) ?
C46 C47 . 1.522(4) ?
C46 C52 . 1.528(4) ?
C46 C53 . 1.541(4) ?
C47 C48 . 1.496(4) ?
C48 C49 . 1.329(4) ?
C48 C51 . 1.508(4) ?
C49 C50 . 1.442(4) ?
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
C5 H5A N22 0.97 2.84 3.744(5) 155
C7 H7B N22 0.97 2.88 3.723(4) 146
C29 H29 N43 0.93 2.65 3.574(4) 173
C45 H45A N21 0.97 2.67 3.624(4) 168
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
C10 N1 N2 N3 -0.4(4)
N1 N2 N3 N4 0.2(4)
N2 N3 N4 C10 0.1(3)
N2 N3 N4 C5 -178.5(3)
C30 N21 N22 N23 0.3(4)
N21 N22 N23 N24 0.1(4)
N22 N23 N24 C30 -0.4(3)
N22 N23 N24 C25 178.4(3)
C50 N41 N42 N43 0.1(4)
N41 N42 N43 N44 0.2(4)
N42 N43 N44 C50 -0.4(4)
N42 N43 N44 C45 178.6(3)
C10 N4 C5 C6 41.5(5)
N3 N4 C5 C6 -140.2(3)
N4 C5 C6 C7 -72.0(4)
N4 C5 C6 C12 52.4(4)
N4 C5 C6 C13 171.0(3)
C5 C6 C7 C8 64.0(4)
C12 C6 C7 C8 -60.3(4)
C13 C6 C7 C8 180.0(3)
C6 C7 C8 C9 -24.2(5)
C6 C7 C8 C11 156.4(3)
C7 C8 C9 C10 -0.8(6)
C11 C8 C9 C10 178.5(3)
N3 N4 C10 N1 -0.4(3)
C5 N4 C10 N1 178.0(3)
N3 N4 C10 C9 178.7(3)
C5 N4 C10 C9 -2.9(5)
N2 N1 C10 N4 0.5(4)
N2 N1 C10 C9 -178.7(3)
C8 C9 C10 N4 -4.6(6)
C8 C9 C10 N1 174.4(3)
C30 N24 C25 C26 -40.0(5)
N23 N24 C25 C26 141.6(3)
N24 C25 C26 C27 71.7(4)
N24 C25 C26 C33 -53.4(4)
N24 C25 C26 C32 -171.1(3)
C25 C26 C27 C28 -64.9(4)
C33 C26 C27 C28 60.2(4)
C32 C26 C27 C28 179.2(3)
C26 C27 C28 C29 24.5(5)
C26 C27 C28 C31 -156.3(3)
C27 C28 C29 C30 1.0(6)
C31 C28 C29 C30 -178.1(3)
N23 N24 C30 N21 0.5(3)
C25 N24 C30 N21 -178.1(3)
N23 N24 C30 C29 180.0(3)
C25 N24 C30 C29 1.4(5)
N22 N21 C30 N24 -0.5(3)
N22 N21 C30 C29 -180.0(3)
C28 C29 C30 N24 5.0(6)
C28 C29 C30 N21 -175.6(3)
C50 N44 C45 C46 -44.6(5)
N43 N44 C45 C46 136.6(3)
N44 C45 C46 C47 73.5(4)
N44 C45 C46 C52 -50.2(4)
N44 C45 C46 C53 -168.6(3)
C52 C46 C47 C48 63.0(4)
C45 C46 C47 C48 -60.9(4)
C53 C46 C47 C48 -177.2(3)
C46 C47 C48 C49 20.9(5)
C46 C47 C48 C51 -160.3(3)
C47 C48 C49 C50 -0.2(6)
C51 C48 C49 C50 -178.9(3)
N43 N44 C50 N41 0.4(4)
C45 N44 C50 N41 -178.5(3)
N43 N44 C50 C49 -178.7(3)
C45 N44 C50 C49 2.4(5)
N42 N41 C50 N44 -0.3(4)
N42 N41 C50 C49 178.9(3)
C48 C49 C50 N44 8.5(6)
C48 C49 C50 N41 -170.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24732091
