#------------------------------------------------------------------------------
#$Date: 2015-10-09 10:15:30 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161176 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/63/7036388.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_7036388
loop_
_publ_author_name
'Izsák, Dániel'
'Klapötke, Thomas M'
'Pflüger, Carolin'
_publ_section_title
;
 Energetic derivatives of 5-(5-amino-2H-1,2,3-triazol-4-yl)-1H-tetrazole.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17054
_journal_page_last               17063
_journal_paper_doi               10.1039/c5dt03044g
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C10 H11 N5 O'
_chemical_formula_sum            'C10 H11 N5 O'
_chemical_formula_weight         217.227
_chemical_name_systematic        4-Amino-1-benzyl-1,2,3-triazol-5-amide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Mon Jun 30 10:27:59 2014'
;
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-16 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.655(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.731(4)
_cell_length_b                   7.423(2)
_cell_length_c                   11.188(4)
_cell_measurement_reflns_used    3097
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.1980
_cell_measurement_theta_min      4.4190
_cell_volume                     972.3(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
'PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_collimation    0.5
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6884
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.14
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2669
_exptl_crystal_size_mid          0.1266
_exptl_crystal_size_min          0.1172
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0318
_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)+(0.0347P)²+0.2924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                1738
_reflns_number_total             1980
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5dt03044g2.cif
_cod_data_source_block           jx203
_cod_depositor_comments
'Adding full bibliography for 7036388--7036389.cif.'
_cod_database_code               7036388
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N4 N 0.46432(9) 1.33291(16) 0.62969(11) 0.0271(3) Uani 1 1 d
O1 O 0.42615(7) 1.30466(11) 0.42869(8) 0.0257(2) Uani 1 1 d
N1 N 0.29663(8) 0.80343(13) 0.52301(9) 0.0179(2) Uani 1 1 d
N2 N 0.32087(9) 0.82578(14) 0.64403(9) 0.0234(2) Uani 1 1 d
N3 N 0.36703(8) 0.98454(14) 0.65923(9) 0.0228(2) Uani 1 1 d
C3 C 0.42367(9) 1.24309(15) 0.53154(11) 0.0201(3) Uani 1 1 d
N5 N 0.31186(9) 0.96995(15) 0.34241(9) 0.0226(2) Uani 1 1 d
C1 C 0.37356(9) 1.06566(15) 0.55064(10) 0.0183(2) Uani 1 1 d
C2 C 0.32821(9) 0.94956(15) 0.46225(10) 0.0160(2) Uani 1 1 d
C4 C 0.24396(10) 0.63777(16) 0.47531(12) 0.0219(3) Uani 1 1 d
C5 C 0.12050(10) 0.66243(15) 0.43012(11) 0.0190(3) Uani 1 1 d
C10 C 0.04516(10) 0.75753(17) 0.49658(12) 0.0243(3) Uani 1 1 d
C9 C -0.06899(11) 0.77210(18) 0.45668(13) 0.0281(3) Uani 1 1 d
C8 C -0.10816(11) 0.69009(17) 0.35077(12) 0.0265(3) Uani 1 1 d
C7 C -0.03363(11) 0.59242(18) 0.28531(12) 0.0284(3) Uani 1 1 d
C6 C 0.08080(11) 0.58057(17) 0.32427(12) 0.0254(3) Uani 1 1 d
H3 H 0.3496(13) 1.062(2) 0.3139(14) 0.035(4) Uiso 1 1 d
H4 H 0.3041(13) 0.872(2) 0.2933(15) 0.037(4) Uiso 1 1 d
H4A H 0.2509(11) 0.552(2) 0.5430(13) 0.025(4) Uiso 1 1 d
H4B H 0.2893(12) 0.5946(19) 0.4102(13) 0.027(4) Uiso 1 1 d
H8A H -0.1894(12) 0.7033(19) 0.3220(13) 0.028(4) Uiso 1 1 d
H6A H 0.1355(13) 0.514(2) 0.2791(14) 0.035(4) Uiso 1 1 d
H7A H -0.0610(13) 0.531(2) 0.2116(15) 0.037(4) Uiso 1 1 d
H9A H -0.1228(13) 0.837(2) 0.5050(14) 0.033(4) Uiso 1 1 d
H10A H 0.0716(12) 0.815(2) 0.5709(14) 0.029(4) Uiso 1 1 d
H2 H 0.5005(14) 1.439(3) 0.6202(15) 0.045(5) Uiso 1 1 d
H1 H 0.4691(13) 1.277(2) 0.6987(15) 0.031(4) Uiso 1 1 d
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N4 H2 118.7(11)
C3 N4 H1 118.9(10)
H2 N4 H1 120.9(14)
C2 N1 N2 110.73(9)
C2 N1 C4 128.15(10)
N2 N1 C4 121.12(10)
N3 N2 N1 107.19(9)
N2 N3 C1 109.25(10)
O1 C3 N4 123.13(12)
O1 C3 C1 120.03(11)
N4 C3 C1 116.84(12)
C2 N5 H3 113.7(10)
C2 N5 H4 120.8(10)
H3 N5 H4 115.4(15)
N3 C1 C2 108.62(11)
N3 C1 C3 125.02(11)
C2 C1 C3 126.33(11)
N1 C2 N5 124.47(11)
N1 C2 C1 104.21(11)
N5 C2 C1 131.27(11)
N1 C4 C5 113.15(10)
N1 C4 H4A 104.4(8)
C5 C4 H4A 111.4(8)
N1 C4 H4B 108.0(8)
C5 C4 H4B 110.1(8)
H4A C4 H4B 109.7(12)
C10 C5 C6 119.45(11)
C10 C5 C4 120.80(11)
C6 C5 C4 119.65(11)
C5 C10 C9 120.18(12)
C5 C10 H10A 120.4(9)
C9 C10 H10A 119.5(8)
C8 C9 C10 120.11(12)
C8 C9 H9A 119.8(9)
C10 C9 H9A 120.1(9)
C7 C8 C9 119.86(12)
C7 C8 H8A 120.5(8)
C9 C8 H8A 119.6(8)
C8 C7 C6 119.94(12)
C8 C7 H7A 120.4(9)
C6 C7 H7A 119.6(9)
C5 C6 C7 120.44(12)
C5 C6 H6A 117.9(9)
C7 C6 H6A 121.7(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N4 C3 1.3458(16)
N4 H2 0.902(19)
N4 H1 0.876(17)
O1 C3 1.2402(16)
N1 C2 1.3447(16)
N1 N2 1.3757(15)
N1 C4 1.4617(16)
N2 N3 1.3036(16)
N3 C1 1.3625(16)
C3 C1 1.4635(18)
N5 C2 1.3508(16)
N5 H3 0.882(17)
N5 H4 0.911(17)
C1 C2 1.3916(16)
C4 C5 1.5144(17)
C4 H4A 0.988(15)
C4 H4B 0.983(15)
C5 C10 1.3843(17)
C5 C6 1.3851(18)
C10 C9 1.3885(19)
C10 H10A 0.967(15)
C9 C8 1.384(2)
C9 H9A 0.984(16)
C8 C7 1.381(2)
C8 H8A 0.991(14)
C7 C6 1.3875(19)
C7 H7A 0.979(16)
C6 H6A 0.975(16)
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
C2 N1 N2 N3 0.12(12)
C4 N1 N2 N3 179.88(10)
N1 N2 N3 C1 -0.15(12)
N2 N3 C1 C2 0.12(13)
N2 N3 C1 C3 -178.04(10)
O1 C3 C1 N3 179.50(10)
N4 C3 C1 N3 -1.21(16)
O1 C3 C1 C2 1.66(17)
N4 C3 C1 C2 -179.06(11)
N2 N1 C2 N5 -177.71(10)
C4 N1 C2 N5 2.55(18)
N2 N1 C2 C1 -0.04(12)
C4 N1 C2 C1 -179.78(10)
N3 C1 C2 N1 -0.05(12)
C3 C1 C2 N1 178.09(10)
N3 C1 C2 N5 177.39(11)
C3 C1 C2 N5 -4.47(19)
C2 N1 C4 C5 -72.22(15)
N2 N1 C4 C5 108.07(12)
N1 C4 C5 C10 -45.16(15)
N1 C4 C5 C6 138.45(12)
C6 C5 C10 C9 -0.65(18)
C4 C5 C10 C9 -177.05(11)
C5 C10 C9 C8 0.6(2)
C10 C9 C8 C7 0.5(2)
C9 C8 C7 C6 -1.62(19)
C10 C5 C6 C7 -0.44(18)
C4 C5 C6 C7 176.00(11)
C8 C7 C6 C5 1.59(19)
