data_des127
_audit_creation_date               2019-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/1'
_publ_contact_author
;
  Dyakonenko V.V.
  SSI "Institute for Single Crystals"
  National Academy of Sciences of Ukraine
  60 Nauki ave.
  Kharkiv, 61001
  Ukraine
;
_publ_contact_author_phone   '380 57 341 02 58'
_publ_contact_author_fax     '380 57 341 02 73'
_publ_contact_author_email   vika@xray.isc.kharkov.com
_publ_contact_author_id_orcid       0000-0003-4613-172X

_publ_requested_journal      'test'

_publ_contact_letter
;
 Paper containing this structure has been
 submitted to Beilstein Journal of Organic Chemistry
;

_iucr_compatibility_tag       ACTA95

_publ_section_title
;
Multicomponent synthesis in water of low molecular
mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
;
loop_
_publ_author_name
'Tkachenko I.G.'
'Komykhov S.A.'
'Musatov V.I.'
'Dyakonenko V.V.'
'Shishkina S.V.'
'Diachkov M.V.'
'Chebanov V.A.'
'Desenko S.M.'

_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C8 H11 N5 O2'
_chemical_formula_sum              'C8 H11 N5 O2'
_chemical_formula_weight           209.22
_chemical_melting_point            ?
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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     4.2983(5)
_cell_length_b                     9.4739(8)
_cell_length_c                     13.1398(14)
_cell_angle_alpha                  73.252(8)
_cell_angle_beta                   88.290(9)
_cell_angle_gamma                  79.628(8)
_cell_volume                       503.87(9)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      480
_cell_measurement_temperature      293
_cell_measurement_theta_max        24.0890
_cell_measurement_theta_min        4.3880
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.104
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.44568
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.379
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               220
_exptl_crystal_size_max            0.5
_exptl_crystal_size_mid            0.4
_exptl_crystal_size_min            0.2
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0311
_diffrn_reflns_av_unetI/netI       0.0682
_diffrn_reflns_Laue_measured_fraction_full  0.995
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         5
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         14
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              3905
_diffrn_reflns_point_group_measured_fraction_full  0.995
_diffrn_reflns_point_group_measured_fraction_max  0.996
_diffrn_reflns_theta_full          26.000
_diffrn_reflns_theta_max           27.496
_diffrn_reflns_theta_min           3.156
_diffrn_ambient_temperature        293
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   16.1827
_diffrn_detector_type              Sapphire3
_diffrn_measured_fraction_theta_full  0.995
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -74.00   -3.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3583  -77.0000 -150.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00   41.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -57.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   65.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -99.0000  150.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega   59.00   96.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   57.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   66.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645  -99.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega   59.00   88.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       26.7645   57.0000 -180.0000 29
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'Xcalibur, Sapphire3'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_UB_11        -0.0745608000
_diffrn_orient_matrix_UB_12        -0.0005517000
_diffrn_orient_matrix_UB_13        -0.0472836000
_diffrn_orient_matrix_UB_21        -0.0040109000
_diffrn_orient_matrix_UB_22        0.0782115000
_diffrn_orient_matrix_UB_23        -0.0208713000
_diffrn_orient_matrix_UB_31        0.1502772000
_diffrn_orient_matrix_UB_32        -0.0140813000
_diffrn_orient_matrix_UB_33        -0.0225434000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1158
_reflns_number_total               2320
_reflns_odcompleteness_completeness  87.26
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       32.33
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.167
_refine_diff_density_min           -0.199
_refine_diff_density_rms           0.038
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.978
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       138
_refine_ls_number_reflns           2320
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1347
_refine_ls_R_factor_gt             0.0620
_refine_ls_restrained_S_all        0.978
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0582P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1355
_refine_ls_wR_factor_ref           0.1710
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 0.7369(5) 0.3414(2) 0.11539(14) 0.0801(6) Uani 1 1 d . . . . .
 O2 O 0.6884(4) 0.5283(2) 0.18983(14) 0.0670(5) Uani 1 1 d . . . . .
 N1 N 0.0583(5) 0.1397(2) 0.55735(17) 0.0655(6) Uani 1 1 d . . . . .
 N2 N 0.0850(6) 0.2445(3) 0.60861(18) 0.0760(7) Uani 1 1 d . . . . .
 N3 N 0.2195(6) 0.3497(3) 0.55021(17) 0.0703(7) Uani 1 1 d . . . . .
 N4 N 0.2870(5) 0.3145(2) 0.45747(16) 0.0561(6) Uani 1 1 d . . . . .
 N5 N 0.2298(5) 0.1242(2) 0.38391(16) 0.0614(6) Uani 1 1 d . . . . .
 H5 H 0.159900 0.042979 0.388923 0.074 Uiso 1 1 calc R . . . .
 C1 C 0.1870(5) 0.1882(3) 0.4635(2) 0.0525(6) Uani 1 1 d . . . . .
 C2 C 0.4196(6) 0.4072(3) 0.36460(19) 0.0586(7) Uani 1 1 d . . . . .
 H2A H 0.614866 0.431735 0.384053 0.070 Uiso 1 1 calc R . . . .
 H2B H 0.272166 0.499857 0.334973 0.070 Uiso 1 1 calc R . . . .
 C3 C 0.4831(5) 0.3198(3) 0.28343(19) 0.0529(6) Uani 1 1 d . . . . .
 C4 C 0.3869(5) 0.1896(3) 0.29370(19) 0.0537(6) Uani 1 1 d . . . . .
 C5 C 0.4272(7) 0.0978(3) 0.2173(2) 0.0707(8) Uani 1 1 d . . . . .
 H5A H 0.319223 0.014422 0.242773 0.106 Uiso 1 1 calc GR . . . .
 H5B H 0.648207 0.061498 0.210964 0.106 Uiso 1 1 calc GR . . . .
 H5C H 0.340001 0.158457 0.148952 0.106 Uiso 1 1 calc GR . . . .
 C6 C 0.6482(6) 0.3916(3) 0.1877(2) 0.0578(7) Uani 1 1 d . . . . .
 C7 C 0.8319(7) 0.6164(3) 0.0962(2) 0.0732(8) Uani 1 1 d . . . . .
 H7A H 0.715863 0.623057 0.032331 0.088 Uiso 1 1 calc R . . . .
 H7B H 1.049135 0.569206 0.090697 0.088 Uiso 1 1 calc R . . . .
 C8 C 0.8217(9) 0.7678(4) 0.1082(3) 0.1069(12) Uani 1 1 d . . . . .
 H8A H 0.925453 0.826281 0.049606 0.160 Uiso 1 1 calc GR . . . .
 H8B H 0.927667 0.759578 0.173555 0.160 Uiso 1 1 calc GR . . . .
 H8C H 0.605512 0.815801 0.109374 0.160 Uiso 1 1 calc GR . . . .

loop_
  _atom_site_aniso_label
  _atom_site_aniso_U_11
  _atom_site_aniso_U_22
  _atom_site_aniso_U_33
  _atom_site_aniso_U_23
  _atom_site_aniso_U_13
  _atom_site_aniso_U_12
 O1 0.1049(15) 0.0827(14) 0.0622(13) -0.0351(10) 0.0243(11) -0.0211(11)
 O2 0.0763(12) 0.0681(13) 0.0621(11) -0.0243(9) 0.0145(9) -0.0202(9)
 N1 0.0844(15) 0.0638(14) 0.0523(14) -0.0211(11) 0.0056(11) -0.0168(11)
 N2 0.1118(19) 0.0693(16) 0.0564(14) -0.0284(12) 0.0109(13) -0.0248(14)
 N3 0.1003(18) 0.0673(15) 0.0542(14) -0.0296(11) 0.0088(13) -0.0239(13)
 N4 0.0688(13) 0.0558(13) 0.0491(12) -0.0223(10) 0.0012(10) -0.0134(10)
 N5 0.0761(15) 0.0573(13) 0.0601(14) -0.0276(11) 0.0093(11) -0.0201(11)
 C1 0.0549(14) 0.0508(15) 0.0530(16) -0.0172(11) -0.0002(12) -0.0086(11)
 C2 0.0737(17) 0.0574(16) 0.0530(15) -0.0236(12) 0.0056(13) -0.0205(13)
 C3 0.0543(14) 0.0576(15) 0.0488(15) -0.0200(11) 0.0014(11) -0.0079(11)
 C4 0.0541(14) 0.0536(15) 0.0524(15) -0.0177(11) -0.0006(12) -0.0031(12)
 C5 0.0892(19) 0.0635(18) 0.0672(18) -0.0319(14) 0.0068(15) -0.0132(14)
 C6 0.0570(15) 0.0620(18) 0.0573(18) -0.0222(13) -0.0015(12) -0.0095(12)
 C7 0.0793(18) 0.086(2) 0.0596(18) -0.0217(15) 0.0149(14) -0.0294(16)
 C8 0.159(3) 0.082(2) 0.093(2) -0.0289(19) 0.025(2) -0.055(2)

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C6 1.203(3) . ?
 O2 C6 1.345(3) . ?
 O2 C7 1.462(3) . ?
 N1 N2 1.373(3) . ?
 N1 C1 1.328(3) . ?
 N2 N3 1.287(3) . ?
 N3 N4 1.363(3) . ?
 N4 C1 1.323(3) . ?
 N4 C2 1.451(3) . ?
 N5 H5 0.8600 . ?
 N5 C1 1.345(3) . ?
 N5 C4 1.387(3) . ?
 C2 H2A 0.9700 . ?
 C2 H2B 0.9700 . ?
 C2 C3 1.519(3) . ?
 C3 C4 1.340(3) . ?
 C3 C6 1.475(3) . ?
 C4 C5 1.495(3) . ?
 C5 H5A 0.9600 . ?
 C5 H5B 0.9600 . ?
 C5 H5C 0.9600 . ?
 C7 H7A 0.9700 . ?
 C7 H7B 0.9700 . ?
 C7 C8 1.481(4) . ?
 C8 H8A 0.9600 . ?
 C8 H8B 0.9600 . ?
 C8 H8C 0.9600 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C6 O2 C7 116.1(2) . . ?
 C1 N1 N2 104.6(2) . . ?
 N3 N2 N1 111.4(2) . . ?
 N2 N3 N4 106.0(2) . . ?
 N3 N4 C2 125.5(2) . . ?
 C1 N4 N3 108.4(2) . . ?
 C1 N4 C2 125.9(2) . . ?
 C1 N5 H5 120.1 . . ?
 C1 N5 C4 119.8(2) . . ?
 C4 N5 H5 120.1 . . ?
 N1 C1 N5 128.9(2) . . ?
 N4 C1 N1 109.5(2) . . ?
 N4 C1 N5 121.6(2) . . ?
 N4 C2 H2A 110.1 . . ?
 N4 C2 H2B 110.1 . . ?
 N4 C2 C3 108.0(2) . . ?
 H2A C2 H2B 108.4 . . ?
 C3 C2 H2A 110.1 . . ?
 C3 C2 H2B 110.1 . . ?
 C4 C3 C2 123.6(2) . . ?
 C4 C3 C6 121.0(2) . . ?
 C6 C3 C2 115.3(2) . . ?
 N5 C4 C5 111.9(2) . . ?
 C3 C4 N5 120.3(2) . . ?
 C3 C4 C5 127.8(2) . . ?
 C4 C5 H5A 109.5 . . ?
 C4 C5 H5B 109.5 . . ?
 C4 C5 H5C 109.5 . . ?
 H5A C5 H5B 109.5 . . ?
 H5A C5 H5C 109.5 . . ?
 H5B C5 H5C 109.5 . . ?
 O1 C6 O2 122.4(2) . . ?
 O1 C6 C3 127.5(3) . . ?
 O2 C6 C3 110.2(2) . . ?
 O2 C7 H7A 110.1 . . ?
 O2 C7 H7B 110.1 . . ?
 O2 C7 C8 107.8(2) . . ?
 H7A C7 H7B 108.5 . . ?
 C8 C7 H7A 110.1 . . ?
 C8 C7 H7B 110.1 . . ?
 C7 C8 H8A 109.5 . . ?
 C7 C8 H8B 109.5 . . ?
 C7 C8 H8C 109.5 . . ?
 H8A C8 H8B 109.5 . . ?
 H8A C8 H8C 109.5 . . ?
 H8B C8 H8C 109.5 . . ?

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
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 N1 N2 N3 N4 -0.3(3) . . . . ?
 N2 N1 C1 N4 0.1(3) . . . . ?
 N2 N1 C1 N5 177.8(2) . . . . ?
 N2 N3 N4 C1 0.4(3) . . . . ?
 N2 N3 N4 C2 175.3(2) . . . . ?
 N3 N4 C1 N1 -0.3(3) . . . . ?
 N3 N4 C1 N5 -178.2(2) . . . . ?
 N3 N4 C2 C3 175.1(2) . . . . ?
 N4 C2 C3 C4 8.6(3) . . . . ?
 N4 C2 C3 C6 -174.21(18) . . . . ?
 C1 N1 N2 N3 0.1(3) . . . . ?
 C1 N4 C2 C3 -10.9(3) . . . . ?
 C1 N5 C4 C3 -3.1(3) . . . . ?
 C1 N5 C4 C5 176.7(2) . . . . ?
 C2 N4 C1 N1 -175.2(2) . . . . ?
 C2 N4 C1 N5 6.9(4) . . . . ?
 C2 C3 C4 N5 -2.4(4) . . . . ?
 C2 C3 C4 C5 177.8(2) . . . . ?
 C2 C3 C6 O1 176.2(3) . . . . ?
 C2 C3 C6 O2 -4.4(3) . . . . ?
 C4 N5 C1 N1 -176.3(2) . . . . ?
 C4 N5 C1 N4 1.1(4) . . . . ?
 C4 C3 C6 O1 -6.5(4) . . . . ?
 C4 C3 C6 O2 172.9(2) . . . . ?
 C6 O2 C7 C8 173.5(2) . . . . ?
 C6 C3 C4 N5 -179.5(2) . . . . ?
 C6 C3 C4 C5 0.7(4) . . . . ?
 C7 O2 C6 O1 3.2(4) . . . . ?
 C7 O2 C6 C3 -176.3(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
