#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/72/2207220.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_2207220
loop_
_publ_author_name
'Lyakhov, Alexander S.'
'Sergei V. Voitekhovich'
'Ivashkevich, Ludmila S.'
'Gaponik, Pavel N.'
_publ_section_title
;
 5-Amino-1-methyl-4H-tetrazolium picrate
;
_journal_coeditor_code           FL6192
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3645
_journal_page_last               o3647
_journal_paper_doi               10.1107/S1600536805031880
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C2 H6 N5 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C2 H6 N5 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C8 H8 N8 O7'
_chemical_formula_weight         328.22
_chemical_name_systematic
;
5-Amino-1-methyl-4H-tetrazolium picrate
;
_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                107.311(14)
_cell_angle_beta                 100.662(14)
_cell_angle_gamma                98.548(15)
_cell_formula_units_Z            2
_cell_length_a                   5.9278(11)
_cell_length_b                   10.234(2)
_cell_length_c                   11.6013(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      22.0
_cell_measurement_theta_min      16.4
_cell_volume                     644.6(2)
_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) and PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      292(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  0.0092
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4267
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0439
_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)+(0.075P)²+0.1158P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1335
_reflns_number_gt                3152
_reflns_number_total             3796
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6192.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).

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).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2207220
_cod_database_fobs_code          2207220
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_type_symbol
N1 0.34719(17) 0.85997(10) 0.78897(9) 0.0355(2) Uani d . 1 N
N2 0.5109(2) 0.98214(12) 0.82422(11) 0.0475(3) Uani d . 1 N
N3 0.6512(2) 0.96517(13) 0.75340(12) 0.0520(3) Uani d . 1 N
N4 0.58207(19) 0.83245(12) 0.67184(10) 0.0425(2) Uani d . 1 N
H4 0.655(4) 0.795(2) 0.6101(19) 0.071(6) Uiso d . 1 H
C5 0.39139(19) 0.76622(12) 0.69277(10) 0.0338(2) Uani d . 1 C
C6 0.1617(2) 0.84457(15) 0.85306(13) 0.0469(3) Uani d . 1 C
H6A 0.0275 0.8723 0.8149 0.070 Uiso calc R 1 H
H6B 0.2169 0.9028 0.9389 0.070 Uiso calc R 1 H
H6C 0.1182 0.7484 0.8478 0.070 Uiso calc R 1 H
N7 0.2718(2) 0.63716(12) 0.63062(11) 0.0472(3) Uani d D 1 N
H7A 0.329(3) 0.5867(17) 0.5759(13) 0.057 Uiso d D 1 H
H7B 0.154(2) 0.6037(19) 0.6542(16) 0.057 Uiso d D 1 H
C8 0.3783(2) 0.32486(11) 0.63456(10) 0.0335(2) Uani d . 1 C
C9 0.5613(2) 0.38219(11) 0.74857(10) 0.0355(2) Uani d . 1 C
C10 0.5415(2) 0.36023(12) 0.85830(10) 0.0364(2) Uani d . 1 C
H10 0.668(3) 0.3957(17) 0.9299(15) 0.046(4) Uiso d . 1 H
C11 0.3360(2) 0.27969(11) 0.86185(10) 0.0357(2) Uani d . 1 C
C12 0.1508(2) 0.21726(12) 0.75710(11) 0.0361(2) Uani d . 1 C
H12 0.007(3) 0.1659(18) 0.7606(15) 0.049(4) Uiso d . 1 H
C13 0.1760(2) 0.23760(11) 0.64826(10) 0.0336(2) Uani d . 1 C
N14 0.7830(2) 0.46843(11) 0.75269(11) 0.0444(2) Uani d . 1 N
N15 -0.02163(19) 0.16891(11) 0.54043(10) 0.0399(2) Uani d . 1 N
N16 0.3134(2) 0.25927(11) 0.97752(10) 0.0441(3) Uani d . 1 N
O1 0.38597(18) 0.34910(9) 0.53556(8) 0.0439(2) Uani d . 1 O
O2 0.8017(3) 0.50964(16) 0.66558(12) 0.0821(5) Uani d . 1 O
O3 0.9449(2) 0.49832(15) 0.84373(13) 0.0697(4) Uani d . 1 O
O4 0.01818(19) 0.12325(11) 0.43718(8) 0.0506(2) Uani d . 1 O
O5 -0.21971(18) 0.15707(14) 0.55753(11) 0.0618(3) Uani d . 1 O
O6 0.4698(2) 0.32263(12) 1.07161(9) 0.0582(3) Uani d . 1 O
O7 0.1383(3) 0.17898(14) 0.97687(11) 0.0709(4) Uani d . 1 O
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 109.22(10)
C5 N1 C6 129.06(11)
N2 N1 C6 121.71(10)
N3 N2 N1 108.05(11)
N2 N3 N4 108.06(11)
C5 N4 N3 109.88(11)
C5 N4 H4 125.4(14)
N3 N4 H4 124.7(14)
N7 C5 N4 127.25(11)
N7 C5 N1 127.96(11)
N4 C5 N1 104.78(10)
N1 C6 H6A 109.5
N1 C6 H6B 109.5
H6A C6 H6B 109.5
N1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C5 N7 H7A 117.2(13)
C5 N7 H7B 119.4(13)
H7A N7 H7B 122.6(19)
O1 C8 C9 125.30(11)
O1 C8 C13 122.76(11)
C9 C8 C13 111.91(9)
C10 C9 C8 123.85(10)
C10 C9 N14 115.77(11)
C8 C9 N14 120.38(10)
C9 C10 C11 119.17(11)
C9 C10 H10 121.3(10)
C11 C10 H10 119.4(10)
C10 C11 C12 121.75(10)
C10 C11 N16 119.13(11)
C12 C11 N16 119.11(11)
C13 C12 C11 118.19(11)
C13 C12 H12 120.1(10)
C11 C12 H12 121.7(10)
C12 C13 C8 125.01(10)
C12 C13 N15 116.32(10)
C8 C13 N15 118.63(9)
O3 N14 O2 121.71(12)
O3 N14 C9 118.72(11)
O2 N14 C9 119.57(12)
O5 N15 O4 123.08(12)
O5 N15 C13 118.05(11)
O4 N15 C13 118.85(10)
O7 N16 O6 122.86(12)
O7 N16 C11 118.30(12)
O6 N16 C11 118.85(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.3344(14) y
N1 N2 1.3641(15) y
N1 C6 1.4516(16) y
N2 N3 1.2678(18) y
N3 N4 1.3543(17) y
N4 C5 1.3295(15) y
N4 H4 0.92(2) ?
C5 N7 1.3163(16) y
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
N7 H7A 0.851(8) ?
N7 H7B 0.859(8) ?
C8 O1 1.2523(13) ?
C8 C9 1.4453(16) ?
C8 C13 1.4483(16) ?
C9 C10 1.3793(16) ?
C9 N14 1.4541(15) ?
C10 C11 1.3807(17) ?
C10 H10 0.946(17) ?
C11 C12 1.3877(17) ?
C11 N16 1.4448(14) ?
C12 C13 1.3700(15) ?
C12 H12 0.949(19) ?
C13 N15 1.4562(15) ?
N14 O3 1.2146(16) ?
N14 O2 1.2218(16) ?
N15 O5 1.2210(15) ?
N15 O4 1.2301(14) ?
N16 O7 1.2219(17) ?
N16 O6 1.2235(16) ?
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
N4 H4 O1 2_666 0.92(2) 1.83(2) 2.6249(15) 143(2)
N4 H4 O4 2_666 0.92(2) 2.22(2) 2.9242(16) 132.5(18)
N7 H7A O1 . 0.851(8) 2.422(15) 3.0496(16) 131.1(16)
N7 H7A O1 2_666 0.851(8) 2.436(15) 3.0621(16) 130.9(16)
N7 H7A O2 2_666 0.851(8) 2.598(14) 3.2303(19) 132.1(15)
N7 H7B O2 1_455 0.859(8) 2.209(9) 3.0472(18) 165.3(17)
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 -0.16(15)
C6 N1 N2 N3 179.33(12)
N1 N2 N3 N4 -0.26(15)
N2 N3 N4 C5 0.59(16)
N3 N4 C5 N7 178.49(13)
N3 N4 C5 N1 -0.67(13)
N2 N1 C5 N7 -178.64(12)
C6 N1 C5 N7 1.9(2)
N2 N1 C5 N4 0.51(13)
C6 N1 C5 N4 -178.93(12)
O1 C8 C9 C10 175.89(11)
C13 C8 C9 C10 -2.16(16)
O1 C8 C9 N14 -4.31(18)
C13 C8 C9 N14 177.64(10)
C8 C9 C10 C11 -0.36(18)
N14 C9 C10 C11 179.83(10)
C9 C10 C11 C12 1.67(18)
C9 C10 C11 N16 -178.66(10)
C10 C11 C12 C13 -0.14(18)
N16 C11 C12 C13 -179.81(10)
C11 C12 C13 C8 -2.84(18)
C11 C12 C13 N15 179.35(10)
O1 C8 C13 C12 -174.27(11)
C9 C8 C13 C12 3.83(16)
O1 C8 C13 N15 3.49(16)
C9 C8 C13 N15 -178.41(10)
C10 C9 N14 O3 10.21(18)
C8 C9 N14 O3 -169.61(12)
C10 C9 N14 O2 -169.33(14)
C8 C9 N14 O2 10.86(19)
C12 C13 N15 O5 33.91(16)
C8 C13 N15 O5 -144.05(12)
C12 C13 N15 O4 -144.71(12)
C8 C13 N15 O4 37.33(15)
C10 C11 N16 O7 -174.36(12)
C12 C11 N16 O7 5.32(18)
C10 C11 N16 O6 5.56(18)
C12 C11 N16 O6 -174.76(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28568749
