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#$Date: 2024-04-05 04:56:28 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291080 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023079.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_2023079
loop_
_publ_author_name
'Domasevitch, Kostiantyn V.'
'Senchyk, Ganna A.'
'Ponomarova, Vira V.'
'Lysenko, Andrey B.'
'Krautscheid, Harald'
_publ_section_title
;
 2-Cyano-2-isonitrosoacetamide--3,4-dimethylpyrazole (1/1): a co-crystal
 of two molecules with agrochemical activities
;
_journal_coeditor_code           HB8093
_journal_issue                   5
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024002809
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C3 H3 N3 O2, C5 H8 N2'
_chemical_formula_moiety         'C3 H3 N3 O2, C5 H8 N2'
_chemical_formula_sum            'C8 H11 N5 O2'
_chemical_formula_weight         209.22
_chemical_name_common
;
2-Cyano-2-isonitrosoacetamide--3,4-dimethylpyrazole (1/1)
;
_chemical_name_systematic
;
2-Cyano-2-isonitrosoacetamide--3,4-dimethylpyrazole (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 91.679(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7082(8)
_cell_length_b                   7.0270(6)
_cell_length_c                   13.8820(10)
_cell_measurement_reflns_used    5398
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      70.625
_cell_measurement_theta_min      4.130
_cell_volume                     1044.12(14)
_computing_cell_refinement
;
X-Area 1.76 (Stoe & Cie, 2016)
;
_computing_data_collection
;
X-Area 1.76 (Stoe & Cie, 2016)
;
_computing_data_reduction
;
X-Area 1.76 (Stoe & Cie, 2016)
;
_computing_molecular_graphics
;
DIAMOND 3.0 (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX 1.70.01 (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      183(2)
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5398
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.625
_diffrn_reflns_theta_min         4.130
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.8816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Stoe LANA; Koziskova et al.,  2016)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0750P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                1392
_reflns_number_total             1998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8093.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023079
_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.
;
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.47628(12) 0.2592(2) 0.13800(12) 0.0444(4) Uani d 1 . .
O O2 0.06840(12) 0.2007(2) 0.22050(11) 0.0436(4) Uani d 1 . .
N N1 0.36927(14) 0.3468(2) 0.16054(13) 0.0362(4) Uani d 1 . .
N N2 0.30041(17) -0.1313(2) 0.15993(15) 0.0496(5) Uani d 1 . .
N N3 0.14496(16) 0.5006(3) 0.20669(15) 0.0429(5) Uani d 1 . .
C C1 0.27806(16) 0.2332(3) 0.17733(14) 0.0325(4) Uani d 1 . .
C C2 0.28894(18) 0.0290(3) 0.16873(16) 0.0385(5) Uani d 1 . .
C C3 0.15325(17) 0.3127(3) 0.20409(14) 0.0347(4) Uani d 1 . .
N N4 0.56206(15) 0.7290(3) 0.10506(14) 0.0452(5) Uani d 1 . .
N N5 0.61296(16) 0.5532(3) 0.10271(13) 0.0432(5) Uani d 1 . .
C C4 0.6459(2) 0.8632(3) 0.08572(17) 0.0446(5) Uani d 1 . .
C C5 0.75761(17) 0.7737(3) 0.06964(15) 0.0372(5) Uani d 1 . .
C C6 0.73161(17) 0.5800(3) 0.08100(15) 0.0370(5) Uani d 1 . .
C C7 0.8177(2) 0.4129(3) 0.07148(19) 0.0528(6) Uani d 1 . .
H H7A 0.901106 0.458051 0.055338 0.079 Uiso calc 0.44(3) . .
H H7B 0.822636 0.343092 0.132575 0.079 Uiso calc 0.44(3) . .
H H7C 0.785521 0.328565 0.020306 0.079 Uiso calc 0.44(3) . .
H H7D 0.771736 0.295088 0.083475 0.079 Uiso calc 0.56(3) . .
H H7E 0.850206 0.410046 0.006237 0.079 Uiso calc 0.56(3) . .
H H7F 0.887321 0.424574 0.118507 0.079 Uiso calc 0.56(3) . .
C C8 0.88103(19) 0.8605(3) 0.04654(17) 0.0459(5) Uani d 1 . .
H H8A 0.943120 0.759503 0.039086 0.069 Uiso calc 0.31(3) . .
H H8B 0.872516 0.933059 -0.013578 0.069 Uiso calc 0.31(3) . .
H H8C 0.908151 0.945634 0.099005 0.069 Uiso calc 0.31(3) . .
H H8D 0.872738 0.999294 0.043923 0.069 Uiso calc 0.69(3) . .
H H8E 0.943342 0.825738 0.096587 0.069 Uiso calc 0.69(3) . .
H H8F 0.907707 0.813163 -0.015996 0.069 Uiso calc 0.69(3) . .
H H1O 0.532(3) 0.368(5) 0.125(2) 0.087(10) Uiso d 1 . .
H H1N 0.075(2) 0.555(3) 0.2284(15) 0.040(6) Uiso d 1 . .
H H2N 0.212(2) 0.581(3) 0.1930(15) 0.043(6) Uiso d 1 . .
H H3N 0.481(2) 0.751(3) 0.1189(16) 0.056(7) Uiso d 1 . .
H H4 0.619(2) 0.984(4) 0.0875(17) 0.053(7) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 O1 H1O . . 102.0(18) ?
C1 N1 O1 . . 114.49(16) ?
C3 N3 H1N . . 119.3(14) ?
C3 N3 H2N . . 123.0(14) ?
H1N N3 H2N . . 117(2) ?
N1 C1 C2 . . 122.47(17) ?
N1 C1 C3 . . 119.90(17) ?
C2 C1 C3 . . 117.60(16) ?
N2 C2 C1 . . 177.9(2) ?
O2 C3 N3 . . 125.71(18) ?
O2 C3 C1 . . 118.34(18) ?
N3 C3 C1 . . 115.95(17) ?
C4 N4 N5 . . 111.53(17) ?
C4 N4 H3N . . 125.1(15) ?
N5 N4 H3N . . 123.3(15) ?
C6 N5 N4 . . 105.36(17) ?
N4 C4 C5 . . 107.7(2) ?
N4 C4 H4 . . 116.6(16) ?
C5 C4 H4 . . 135.7(16) ?
C4 C5 C6 . . 104.44(18) ?
C4 C5 C8 . . 128.7(2) ?
C6 C5 C8 . . 126.83(18) ?
N5 C6 C5 . . 111.01(18) ?
N5 C6 C7 . . 120.2(2) ?
C5 C6 C7 . . 128.78(19) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
H7D C7 H7E . . 109.5 ?
H7D C7 H7F . . 109.5 ?
H7E C7 H7F . . 109.5 ?
C5 C8 H8A . . 109.5 ?
C5 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C5 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
H8D C8 H8E . . 109.5 ?
H8D C8 H8F . . 109.5 ?
H8E C8 H8F . . 109.5 ?
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
O1 N1 . 1.345(2) ?
O1 H1O . 0.99(3) ?
O2 C3 . 1.229(2) ?
N1 C1 . 1.288(2) ?
N2 C2 . 1.140(3) ?
N3 C3 . 1.323(3) ?
N3 H1N . 0.90(2) ?
N3 H2N . 0.94(2) ?
C1 C2 . 1.445(3) ?
C1 C3 . 1.505(2) ?
N4 C4 . 1.334(3) ?
N4 N5 . 1.351(2) ?
N4 H3N . 0.91(3) ?
N5 C6 . 1.328(3) ?
C4 C5 . 1.376(3) ?
C4 H4 . 0.90(3) ?
C5 C6 . 1.399(3) ?
C5 C8 . 1.499(3) ?
C6 C7 . 1.501(3) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C7 H7D . 0.9800 ?
C7 H7E . 0.9800 ?
C7 H7F . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C8 H8D . 0.9800 ?
C8 H8E . 0.9800 ?
C8 H8F . 0.9800 ?
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
O1 H1O N5 . 0.99(3) 1.60(3) 2.587(2) 176(3) yes
N3 H1N O2 2_555 0.90(2) 1.99(2) 2.890(2) 174(2) yes
N3 H2N N2 1_565 0.94(2) 2.28(2) 3.154(3) 154.0(19) yes
N4 H3N N2 1_565 0.91(3) 2.20(3) 3.085(3) 167(2) yes
C4 H4 O1 1_565 0.90(3) 2.58(3) 3.413(3) 156(2) yes
C8 H8E O2 2_655 0.98 2.69 3.451(3) 134 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 C1 C2 . . . . -2.4(3) ?
O1 N1 C1 C3 . . . . 179.55(16) ?
N1 C1 C3 O2 . . . . -179.37(19) ?
C2 C1 C3 O2 . . . . 2.5(3) ?
N1 C1 C3 N3 . . . . 1.4(3) ?
C2 C1 C3 N3 . . . . -176.80(19) ?
C4 N4 N5 C6 . . . . -0.2(3) ?
N5 N4 C4 C5 . . . . 0.0(3) ?
N4 C4 C5 C6 . . . . 0.1(3) ?
N4 C4 C5 C8 . . . . -179.1(2) ?
N4 N5 C6 C5 . . . . 0.2(2) ?
N4 N5 C6 C7 . . . . -179.6(2) ?
C4 C5 C6 N5 . . . . -0.2(3) ?
C8 C5 C6 N5 . . . . 179.0(2) ?
C4 C5 C6 C7 . . . . 179.6(2) ?
C8 C5 C6 C7 . . . . -1.2(4) ?
