#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/67/2016734.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_2016734
loop_
_publ_author_name
'Lyakhov, Alexander S.'
'Vorobiov, Andrey N.'
'Ivashkevich, Ludmila S.'
'Gaponik, Pavel N.'
_publ_section_title
;Two derivatives of 1,5-disubstituted tetrazoles:
 1-(4-nitrophenyl)-1H-tetrazol-5-amine and
 {(E)-[1-(4-ethoxyphenyl)-1H-tetrazol-5-yl]iminomethyl}dimethylamine
;
_journal_coeditor_code           SK3250
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o414
_journal_page_last               o416
_journal_paper_doi               10.1107/S0108270108019707
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H6 N6 O2'
_chemical_formula_moiety         'C7 H6 N6 O2'
_chemical_formula_sum            'C7 H6 N6 O2'
_chemical_formula_weight         206.18
_chemical_name_systematic
;
1-(4-nitrophenyl)-1H-tetrazol-5-amine
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                68.135(17)
_cell_angle_beta                 74.049(17)
_cell_angle_gamma                63.135(18)
_cell_formula_units_Z            2
_cell_length_a                   7.8891(17)
_cell_length_b                   7.9921(18)
_cell_length_c                   8.5877(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.7
_cell_measurement_theta_min      16.2
_cell_volume                     444.55(19)
_computing_cell_refinement       'R3m software (Nicolet, 1980)'
_computing_data_collection       'R3m software (Nicolet, 1980)'
_computing_data_reduction        'R3m software (Nicolet, 1980)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material
;
PLATON (Spek, 2003) and SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nicolet R3m four-circle'
_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  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5556
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0417
_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)+(0.0697P)²+0.0595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2338
_reflns_number_total             2605
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3250.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (7
times).

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2
times).

'_geom_hbond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (7
times).

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2
times).

'_geom_hbond_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2016734
_cod_database_fobs_code          2016734
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_occupancy
N N1 0.71575(11) 0.30355(12) 0.22691(10) 0.03411(19) Uani d 1
N N2 0.68183(14) 0.30624(14) 0.07743(11) 0.0432(2) Uani d 1
N N3 0.59130(14) 0.19458(15) 0.11762(12) 0.0447(2) Uani d 1
N N4 0.56081(12) 0.11715(13) 0.28830(11) 0.0394(2) Uani d 1
N N6 0.64696(17) 0.14419(17) 0.51962(12) 0.0509(3) Uani d 1
H H6A 0.585(2) 0.074(2) 0.590(2) 0.061(4) Uiso d 1
H H6B 0.671(2) 0.222(2) 0.552(2) 0.065(4) Uiso d 1
C C5 0.63976(13) 0.18612(13) 0.35495(12) 0.0348(2) Uani d 1
C C7 0.82206(13) 0.40546(13) 0.23101(11) 0.03255(19) Uani d 1
C C8 0.76465(15) 0.60463(15) 0.14954(14) 0.0397(2) Uani d 1
H H8 0.653(2) 0.678(2) 0.0916(19) 0.055(4) Uiso d 1
C C9 0.86768(16) 0.70270(15) 0.15807(14) 0.0418(2) Uani d 1
H H9 0.829(2) 0.846(3) 0.098(2) 0.067(5) Uiso d 1
C C10 1.02302(14) 0.59757(14) 0.24793(12) 0.0357(2) Uani d 1
C C11 1.08440(14) 0.39851(15) 0.32524(13) 0.0387(2) Uani d 1
H H11 1.198(2) 0.328(2) 0.3815(18) 0.053(4) Uiso d 1
C C12 0.98186(14) 0.30067(14) 0.31603(14) 0.0387(2) Uani d 1
H H12 1.023(2) 0.159(2) 0.3678(19) 0.054(4) Uiso d 1
N N13 1.12551(14) 0.70192(14) 0.26615(12) 0.0436(2) Uani d 1
O O1 1.05418(16) 0.88076(14) 0.22333(15) 0.0651(3) Uani d 1
O O2 1.27657(13) 0.60462(15) 0.32748(12) 0.0561(2) Uani d 1
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 0.0359(4) 0.0384(4) 0.0364(4) -0.0224(3) -0.0058(3) -0.0088(3)
N2 0.0513(5) 0.0533(5) 0.0382(4) -0.0322(4) -0.0080(4) -0.0108(4)
N3 0.0510(5) 0.0543(5) 0.0440(5) -0.0326(4) -0.0089(4) -0.0130(4)
N4 0.0418(4) 0.0452(4) 0.0437(4) -0.0274(4) -0.0060(3) -0.0125(3)
N6 0.0727(7) 0.0668(6) 0.0381(5) -0.0541(6) -0.0054(4) -0.0089(4)
C5 0.0347(4) 0.0368(4) 0.0397(5) -0.0212(3) -0.0042(3) -0.0097(3)
C7 0.0331(4) 0.0371(4) 0.0349(4) -0.0211(3) -0.0019(3) -0.0109(3)
C8 0.0406(5) 0.0373(5) 0.0468(5) -0.0188(4) -0.0128(4) -0.0082(4)
C9 0.0471(5) 0.0351(4) 0.0499(5) -0.0218(4) -0.0095(4) -0.0097(4)
C10 0.0372(4) 0.0433(5) 0.0384(4) -0.0250(4) 0.0007(3) -0.0167(4)
C11 0.0343(4) 0.0441(5) 0.0438(5) -0.0209(4) -0.0074(4) -0.0107(4)
C12 0.0365(5) 0.0357(4) 0.0469(5) -0.0191(4) -0.0092(4) -0.0062(4)
N13 0.0473(5) 0.0549(5) 0.0465(5) -0.0328(4) 0.0026(4) -0.0236(4)
O1 0.0708(6) 0.0529(5) 0.0941(8) -0.0357(5) -0.0096(5) -0.0314(5)
O2 0.0524(5) 0.0737(6) 0.0652(5) -0.0371(4) -0.0107(4) -0.0266(5)
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'
O O 0.0106 0.0060 '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 108.08(8)
C5 N1 C7 130.01(8)
N2 N1 C7 121.85(8)
N3 N2 N1 106.07(8)
N2 N3 N4 111.89(8)
C5 N4 N3 105.93(8)
C5 N6 H6A 116.6(11)
C5 N6 H6B 118.3(10)
H6A N6 H6B 120.5(16)
N4 C5 N6 126.25(9)
N4 C5 N1 108.04(9)
N6 C5 N1 125.69(9)
C12 C7 C8 122.04(9)
C12 C7 N1 118.43(8)
C8 C7 N1 119.53(8)
C7 C8 C9 118.74(9)
C7 C8 H8 122.3(9)
C9 C8 H8 118.9(9)
C10 C9 C8 118.59(9)
C10 C9 H9 122.0(10)
C8 C9 H9 119.4(10)
C11 C10 C9 123.05(9)
C11 C10 N13 117.99(9)
C9 C10 N13 118.95(9)
C10 C11 C12 118.27(9)
C10 C11 H11 120.8(9)
C12 C11 H11 120.9(9)
C7 C12 C11 119.26(9)
C7 C12 H12 120.4(9)
C11 C12 H12 120.4(9)
O1 N13 O2 123.36(10)
O1 N13 C10 118.45(10)
O2 N13 C10 118.17(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.3516(12) y
N1 N2 1.3722(12) y
N1 C7 1.4223(11) y
N2 N3 1.2794(12) y
N3 N4 1.3617(13) y
N4 C5 1.3269(12) y
N6 C5 1.3376(13) y
N6 H6A 0.866(16) ?
N6 H6B 0.873(18) ?
C7 C12 1.3857(14) ?
C7 C8 1.3862(14) ?
C8 C9 1.3897(13) ?
C8 H8 0.960(15) ?
C9 C10 1.3819(15) ?
C9 H9 0.999(17) ?
C10 C11 1.3784(15) ?
C10 N13 1.4662(12) ?
C11 C12 1.3874(13) ?
C11 H11 0.966(15) ?
C12 H12 0.977(15) ?
N13 O1 1.2207(14) ?
N13 O2 1.2266(14) ?
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
_geom_hbond_publ_flag
N6 H6A N4 2_656 0.866(16) 2.119(17) 2.9684(14) 166.8(15) y
N6 H6B O2 2_766 0.873(18) 2.234(18) 3.1003(14) 171.9(14) y
C8 H8 N3 2_665 0.960(15) 2.599(16) 3.5286(16) 163.1(13) n
C9 H9 N3 1_565 0.999(17) 2.601(17) 3.4614(18) 144.2(13) n
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 -0.32(11)
C7 N1 N2 N3 177.14(9)
N1 N2 N3 N4 0.48(12)
N2 N3 N4 C5 -0.46(12)
N3 N4 C5 N6 -178.48(11)
N3 N4 C5 N1 0.24(11)
N2 N1 C5 N4 0.04(11)
C7 N1 C5 N4 -177.15(9)
N2 N1 C5 N6 178.77(10)
C7 N1 C5 N6 1.58(17)
C5 N1 C7 C12 52.88(14)
N2 N1 C7 C12 -123.97(11)
C5 N1 C7 C8 -127.63(11)
N2 N1 C7 C8 55.52(13)
C12 C7 C8 C9 -1.96(16)
N1 C7 C8 C9 178.57(9)
C7 C8 C9 C10 -0.18(16)
C8 C9 C10 C11 2.10(17)
C8 C9 C10 N13 -176.38(9)
C9 C10 C11 C12 -1.83(16)
N13 C10 C11 C12 176.65(9)
C8 C7 C12 C11 2.23(16)
N1 C7 C12 C11 -178.30(9)
C10 C11 C12 C7 -0.34(15)
C11 C10 N13 O1 -167.90(10)
C9 C10 N13 O1 10.65(15)
C11 C10 N13 O2 10.41(14)
C9 C10 N13 O2 -171.04(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10438490
