#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/53/2235339.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_2235339
loop_
_publ_author_name
'Yu, Chun-Hua'
'Zhu, Run-Qiang'
_publ_section_title
;
 1H-Pyrazol-2-ium hydrogen oxalate
;
_journal_coeditor_code           ZS2209
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1911
_journal_paper_doi               10.1107/S1600536812023136
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C3 H5 N2 +, C2 H O4 -'
_chemical_formula_moiety         'C3 H5 N2 +, C2 H O4 -'
_chemical_formula_sum            'C5 H6 N2 O4'
_chemical_formula_weight         158.12
_chemical_name_common            'pyrazolium hydrogen oxalate '
_chemical_name_systematic
;
1H-Pyrazol-2-ium hydrogen oxalate
;
_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                117.35(3)
_cell_angle_beta                 97.01(3)
_cell_angle_gamma                93.65(3)
_cell_formula_units_Z            2
_cell_length_a                   3.7286(7)
_cell_length_b                   9.836(2)
_cell_length_c                   10.487(2)
_cell_measurement_reflns_used    1527
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.488
_cell_measurement_theta_min      2.35
_cell_volume                     335.92(15)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku SCXmini CCD'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3484
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.293
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1908
_refine_ls_R_factor_gt           0.0952
_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)+(0.1349P)²+0.0952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2402
_refine_ls_wR_factor_ref         0.2852
_reflns_number_gt                702
_reflns_number_total             1527
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2209.cif
_cod_data_source_block           I
_cod_original_cell_volume        335.92(14)
_cod_database_code               2235339
_cod_database_fobs_code          2235339
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 1.0872(11) 0.0136(5) 0.3057(4) 0.0416(11) Uani d . 1 1
H H1A 1.1595 -0.0585 0.3230 0.050 Uiso d R 1 1
N N2 1.1523(11) 0.1643(5) 0.3992(4) 0.0412(11) Uani d . 1 1
H H2A 1.2729 0.2054 0.4865 0.049 Uiso d R 1 1
C C1 0.9992(15) 0.2395(6) 0.3352(6) 0.0493(15) Uani d . 1 1
H H1 1.0047 0.3461 0.3773 0.059 Uiso calc R 1 1
C C2 0.8307(15) 0.1355(7) 0.1967(6) 0.0505(15) Uani d . 1 1
H H2 0.7020 0.1567 0.1277 0.061 Uiso calc R 1 1
C C3 0.8931(15) -0.0076(7) 0.1818(6) 0.0477(14) Uani d . 1 1
H H3 0.8131 -0.1021 0.0993 0.057 Uiso calc R 1 1
O O1 0.3997(10) 0.8001(4) 0.3600(3) 0.0475(10) Uani d . 1 1
O O2 0.6353(11) 0.5351(4) 0.3418(4) 0.0577(12) Uani d . 1 1
O O3 0.0807(11) 0.6588(4) 0.1355(4) 0.0581(11) Uani d . 1 1
O O4 0.3270(11) 0.4012(4) 0.1179(4) 0.0554(11) Uani d . 1 1
H H4 0.1905 0.4187 0.0612 0.083 Uiso calc R 1 1
C C4 0.2907(14) 0.6762(6) 0.2446(5) 0.0402(13) Uani d . 1 1
C C5 0.4374(14) 0.5304(6) 0.2400(5) 0.0425(13) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
C3 N1 N2 109.3(4)
C3 N1 H1A 125.3
N2 N1 H1A 125.4
C1 N2 N1 108.4(4)
C1 N2 H2A 125.8
N1 N2 H2A 125.8
N2 C1 C2 109.1(5)
N2 C1 H1 125.4
C2 C1 H1 125.4
C1 C2 C3 105.2(5)
C1 C2 H2 127.4
C3 C2 H2 127.4
N1 C3 C2 108.0(5)
N1 C3 H3 126.0
C2 C3 H3 126.0
C5 O4 H4 109.5
O3 C4 O1 127.0(5)
O3 C4 C5 117.3(4)
O1 C4 C5 115.7(4)
O2 C5 O4 122.4(5)
O2 C5 C4 122.1(5)
O4 C5 C4 115.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.325(6)
N1 N2 1.333(5)
N1 H1A 0.8601
N2 C1 1.319(6)
N2 H2A 0.8600
C1 C2 1.372(7)
C1 H1 0.9300
C2 C3 1.380(8)
C2 H2 0.9300
C3 H3 0.9300
O1 C4 1.256(6)
O2 C5 1.202(6)
O3 C4 1.239(6)
O4 C5 1.317(6)
O4 H4 0.8200
C4 C5 1.549(7)
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
N1 H1A O1 1_645 0.86 1.86 2.709(5) 169.6
N2 H2A O1 2_766 0.86 1.92 2.715(5) 152.7
O4 H4 O3 2_565 0.82 1.95 2.679(5) 147.4
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
C3 N1 N2 C1 0.1(6)
N1 N2 C1 C2 0.0(6)
N2 C1 C2 C3 0.0(6)
N2 N1 C3 C2 -0.1(6)
C1 C2 C3 N1 0.1(6)
O3 C4 C5 O2 -178.2(5)
O1 C4 C5 O2 1.9(8)
O3 C4 C5 O4 1.0(7)
O1 C4 C5 O4 -178.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14071859
