#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/49/2214919.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_2214919
loop_
_publ_author_name
'Sarıkavaklı, Nursabah'
'Şahin, Ertan'
'Hökelek, Tuncer'
_publ_section_title
;(1Z,2E)-1-(3,5-Dimethyl-1H-pyrazol-1-yl)ethane-1,2-dione
 dioxime
;
_journal_coeditor_code           XU2297
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3601
_journal_page_last               o3601
_journal_paper_doi               10.1107/S1600536807035490
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H10 N4 O2'
_chemical_formula_moiety         'C7 H10 N4 O2'
_chemical_formula_sum            'C7 H10 N4 O2'
_chemical_formula_weight         182.19
_chemical_name_systematic
;
(1Z,2E)-1-(3,5-Dimethyl-1H-pyrazol-1-yl)-1,2-ethanedione dioxime
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 104.254(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7598(5)
_cell_length_b                   9.8572(6)
_cell_length_c                   9.8140(7)
_cell_measurement_reflns_used    3673
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.0
_cell_volume                     915.08(10)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       'ω scans'
_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  0.065
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26614
_diffrn_reflns_theta_full        30.6
_diffrn_reflns_theta_max         30.6
_diffrn_reflns_theta_min         2.9
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.089
_refine_ls_R_factor_gt           0.060
_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)+(0.072P)²+0.1814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.146
_refine_ls_wR_factor_ref         0.164
_reflns_number_gt                1879
_reflns_number_total             2785
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2297.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214919
_cod_database_fobs_code          2214919
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_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_refinement_flags
_atom_site_occupancy
O O1 -0.12971(15) 0.10253(16) 0.03495(17) 0.0774(5) Uani d . 1
H H1 -0.124(4) 0.034(4) -0.034(4) 0.169(15) Uiso d . 1
O O2 0.29576(13) 0.24903(13) 0.53291(13) 0.0596(4) Uani d . 1
H H2 0.293(3) 0.317(3) 0.601(3) 0.097(8) Uiso d . 1
N N1 0.31551(15) 0.05600(13) 0.23301(13) 0.0479(3) Uani d . 1
N N2 0.24604(14) 0.06268(13) 0.33862(13) 0.0449(3) Uani d . 1
N N3 -0.00111(16) 0.08524(15) 0.13275(16) 0.0586(4) Uani d . 1
N N4 0.16951(15) 0.26301(15) 0.43425(14) 0.0534(4) Uani d . 1
C C1 0.2119(3) -0.0631(2) 0.5483(2) 0.0714(6) Uani d . 1
H H1A 0.2215 0.0189 0.6026 0.107 Uiso calc R 1
H H1B 0.2587 -0.1360 0.6064 0.107 Uiso calc R 1
H H1C 0.1134 -0.0845 0.5139 0.107 Uiso calc R 1
C C2 0.27711(19) -0.04401(17) 0.42716(17) 0.0513(4) Uani d . 1
C C3 0.3714(2) -0.12097(18) 0.37819(19) 0.0598(5) Uani d . 1
H H3 0.4135 -0.2013 0.4172 0.072 Uiso calc R 1
C C4 0.39228(18) -0.05630(17) 0.25889(17) 0.0508(4) Uani d . 1
C C5 0.4841(2) -0.0981(2) 0.1644(2) 0.0705(6) Uani d . 1
H H5A 0.4299 -0.0965 0.0684 0.106 Uiso calc R 1
H H5B 0.5191 -0.1883 0.1884 0.106 Uiso calc R 1
H H5C 0.5623 -0.0365 0.1757 0.106 Uiso calc R 1
C C6 0.14943(18) 0.17055(16) 0.33936(16) 0.0473(4) Uani d . 1
C C7 0.01985(19) 0.17524(18) 0.22847(18) 0.0544(4) Uani d . 1
H H7 -0.048(2) 0.251(2) 0.233(2) 0.073(6) Uiso 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
O1 0.0613(8) 0.0801(10) 0.0744(10) 0.0127(7) -0.0144(7) -0.0193(8)
O2 0.0622(8) 0.0612(8) 0.0500(7) 0.0063(6) 0.0033(6) -0.0149(6)
N1 0.0562(8) 0.0498(7) 0.0380(6) 0.0046(6) 0.0122(6) 0.0029(5)
N2 0.0538(8) 0.0430(7) 0.0376(6) 0.0048(5) 0.0108(5) 0.0000(5)
N3 0.0535(8) 0.0575(8) 0.0561(8) 0.0039(6) -0.0033(6) -0.0062(7)
N4 0.0575(8) 0.0543(8) 0.0463(7) 0.0060(6) 0.0088(6) -0.0067(6)
C1 0.0967(16) 0.0668(12) 0.0581(11) 0.0024(10) 0.0331(11) 0.0104(9)
C2 0.0627(10) 0.0477(9) 0.0435(8) 0.0029(7) 0.0131(7) 0.0044(6)
C3 0.0736(12) 0.0511(10) 0.0548(10) 0.0162(8) 0.0159(8) 0.0101(8)
C4 0.0540(9) 0.0531(9) 0.0435(8) 0.0082(7) 0.0086(7) 0.0001(7)
C5 0.0738(13) 0.0821(14) 0.0588(11) 0.0203(10) 0.0223(9) -0.0025(10)
C6 0.0546(9) 0.0445(8) 0.0422(8) 0.0052(7) 0.0108(6) -0.0017(6)
C7 0.0563(10) 0.0535(9) 0.0500(9) 0.0082(8) 0.0067(7) -0.0036(7)
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
N3 O1 H1 102(2)
N4 O2 H2 104.5(15)
C4 N1 N2 104.85(13)
C2 N2 N1 111.97(13)
C2 N2 C6 128.54(14)
N1 N2 C6 119.41(12)
C7 N3 O1 112.23(15)
C6 N4 O2 112.99(13)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N2 C2 C3 105.65(15)
N2 C2 C1 122.60(16)
C3 C2 C1 131.74(16)
C2 C3 C4 107.00(15)
C2 C3 H3 126.5
C4 C3 H3 126.5
N1 C4 C3 110.52(15)
N1 C4 C5 120.50(16)
C3 C4 C5 128.99(16)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N4 C6 N2 123.49(15)
N4 C6 C7 118.07(15)
N2 C6 C7 118.43(14)
N3 C7 C6 118.92(16)
N3 C7 H7 124.3(12)
C6 C7 H7 116.8(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.3901(19)
O1 H1 0.97(4)
O2 N4 1.3738(18)
O2 H2 0.95(3)
N1 C4 1.326(2)
N2 C2 1.350(2)
N2 N1 1.3727(18)
N2 C6 1.422(2)
N3 C7 1.271(2)
N4 C6 1.283(2)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.368(2)
C2 C1 1.492(3)
C3 H3 0.9300
C4 C3 1.392(2)
C4 C5 1.498(2)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 C7 1.452(2)
C7 H7 1.00(2)
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 H1 N1 3_555 0.97(4) 2.51(4) 3.209(3) 129(3) yes
O1 H1 N3 3_555 0.97(4) 2.10(4) 2.966(3) 149(3) yes
O2 H2 N1 . 0.95(3) 1.78(3) 2.720(2) 172(3) 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
N2 N1 C4 C3 0.52(19)
N2 N1 C4 C5 -179.96(16)
C2 N2 N1 C4 -0.89(18)
C6 N2 N1 C4 -177.87(14)
N1 N2 C2 C3 0.90(19)
C6 N2 C2 C3 177.53(16)
N1 N2 C2 C1 -178.03(16)
C6 N2 C2 C1 -1.4(3)
C2 N2 C6 N4 69.6(2)
N1 N2 C6 N4 -114.00(18)
C2 N2 C6 C7 -109.24(19)
N1 N2 C6 C7 67.2(2)
O1 N3 C7 C6 179.58(15)
O2 N4 C6 N2 1.6(2)
O2 N4 C6 C7 -179.53(14)
N2 C2 C3 C4 -0.5(2)
C1 C2 C3 C4 178.3(2)
N1 C4 C3 C2 0.0(2)
C5 C4 C3 C2 -179.47(19)
N4 C6 C7 N3 179.27(17)
N2 C6 C7 N3 -1.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21184484
2 PubChem 139072834
