#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/56/2105611.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_2105611
loop_
_publ_author_name
'Bianchi, R.'
'Gervasio, G.'
'Viscardi, G.'
_publ_section_title
;
 Experimental Electron-Density Study of 4-Cyanoimidazolium-5-olate at 120
 K
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              66
_journal_page_last               72
_journal_paper_doi               10.1107/S0108768197009269
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C4 H3 N3 O'
_chemical_formula_weight         109.09
_chemical_name_systematic
;
 4-cyano-imidazolium-5-olate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_formula_units_Z            4.00
_cell_length_a                   12.584(3)
_cell_length_b                   9.699(2)
_cell_length_c                   3.674(2)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    120
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     448.4(3)
_diffrn_ambient_temperature      120
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2943
_diffrn_reflns_reduction_process ' ......'
_diffrn_reflns_theta_max         40
_diffrn_reflns_theta_min         1
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.1241
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.6158
_exptl_crystal_description
;
;
_exptl_crystal_F_000             224.0
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.45
_refine_ls_abs_structure_details
;
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   3.432
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_constraints    1
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1528
_refine_ls_R_factor_obs          0.0663
_refine_ls_shift/su_max          0.02
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0733
_reflns_number_observed          2943
_cod_data_source_file            na0081.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C4 H3 N3 O1 '
_cod_database_code               2105611
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z+1/2
x+1/2,-y+1/2,z
-x+1/2,y+1/2,z+1/2
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_type_symbol
N1 0.06690(7) 0.14650(10) -0.2245(6) 0.0127(2) Uani N
C2 0.10536(9) 0.26990(10) -0.3264(6) 0.0128(3) Uani C
N3 0.20649(7) 0.27780(10) -0.2344(5) 0.0126(2) Uani N
C4 0.23606(8) 0.15400(10) -0.0688(6) 0.0115(3) Uani C
C5 0.14657(8) 0.06830(10) -0.0578(6) 0.0112(3) Uani C
C6 0.33803(8) 0.12950(10) 0.0708(7) 0.0130(3) Uani C
N7 0.42156(8) 0.10810(10) 0.1881(6) 0.0193(3) Uani C
O8 0.13303(6) -0.05228(9) 0.07030000 0.0154(2) Uani O
H1 0.0020(10) 0.1190(10) -0.283(7) 0.029(4) Uiso H
H2 0.0640(10) 0.344(2) -0.438(7) 0.024(4) Uiso H
H3 0.2580(10) 0.349(2) -0.293(8) 0.040(5) Uiso H
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
N1 0.0072(3) 0.0102(4) 0.0206(5) -0.0002(3) -0.0022(4) 0.0002(4)
C2 0.0095(4) 0.0109(4) 0.0181(6) 0.0000(4) -0.0015(4) 0.0018(4)
N3 0.0097(3) 0.0093(4) 0.0187(5) -0.0010(3) -0.0018(4) 0.0027(4)
C4 0.0079(4) 0.0093(4) 0.0174(6) -0.0003(3) -0.0014(5) 0.0022(5)
C5 0.0078(4) 0.0097(4) 0.0163(6) 0.0004(3) -0.0008(5) 0.0004(5)
C6 0.0108(4) 0.0102(4) 0.0181(5) -0.0019(3) -0.0016(5) 0.0006(5)
N7 0.0128(4) 0.0177(5) 0.0273(7) -0.0006(4) -0.0049(5) 0.0015(5)
O8 0.0093(3) 0.0096(3) 0.0273(6) -0.0007(3) 0.0005(4) 0.0044(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'N ' 'Nitrogen    ' 0.0061 0.0033 'Int. Tab. C, 4.2.6.8, 6.1.1.4'
'C ' 'Carbon      ' 0.0033 0.0016 'Int. Tab. C, 4.2.6.8, 6.1.1.4'
'O ' 'Oxygen      ' 0.0106 0.0060 'Int. Tab. C, 4.2.6.8, 6.1.1.4'
'H ' 'Hydrogen    ' 0.0000 0.0000 'Int. Tab. C, 4.2.6.8, 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
_geom_angle_publ_flag
C2 N1 C5 110.30(10) yes
C2 N1 H1 122.2(7) yes
C5 N1 H1 127.2(9) yes
N1 C2 N3 109.10(10) yes
N1 C2 H2 125.0(10) yes
N3 C2 H2 125.3(8) yes
C2 N3 C4 108.60(10) yes
C2 N3 H3 128.9(8) yes
C4 N3 H3 122.0(10) yes
N3 C4 C5 108.00(10) yes
N3 C4 C6 123.30(10) yes
C5 C4 C6 128.70(10) yes
N1 C5 C4 104.00(10) yes
N1 C5 O8 124.40(10) yes
C4 C5 O8 131.60(10) yes
C4 C6 N7 179.20(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.344(2) yes
N1 C5 1.398(2) yes
N1 H1 0.890(10) yes
C2 N3 1.319(2) yes
C2 H2 0.980(10) yes
N3 C4 1.397(2) yes
N3 H3 0.970(10) yes
C4 C5 1.4000(10) yes
C4 C6 1.402(2) yes
C5 O8 1.272(2) yes
C6 N7 1.155(2) yes
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 H1 O8 2_554 0.890(10) 1.900(10) 2.7810(10) 176.0(10)
C2 H2 N7 3_454 0.98(2) 2.31(2) 3.151(2) 144.0(10)
N3 H3 O8 4_554 0.97(2) 1.75(2) 2.7040(10) 168.0(10)
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_publ_flag
C5 N1 C2 N3 -0.3(2) no
C5 N1 C2 H2 -176.0(10) no
H1 N1 C2 N3 -173.0(10) no
H1 N1 C2 H2 10(2) no
C2 N1 C5 C4 -0.3(2) no
C2 N1 C5 O8 179.10(10) no
H1 N1 C5 C4 173.0(10) no
H1 N1 C5 O8 -7.0(10) no
N1 C2 N3 C4 0.7(2) no
N1 C2 N3 H3 173(2) no
H2 C2 N3 C4 177.0(10) no
H2 C2 N3 H3 -9(2) no
C2 N3 C4 C5 -0.8(2) no
C2 N3 C4 C6 -178.2(2) no
H3 N3 C4 C5 -173(2) no
H3 N3 C4 C6 9(2) no
N3 C4 C5 N1 0.6(2) no
N3 C4 C5 O8 -178.7(2) no
C6 C4 C5 N1 177.9(2) no
C6 C4 C5 O8 -1.5(3) no
