data_2205937
_publ_section_title
;
 1H-Imidazole-4-carbonitrile
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1704
_journal_page_last               o1706
_journal_paper_doi               10.1107/S1600536805014509
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C4 H3 N3'
_chemical_formula_moiety         'C4 H3 N3'
_chemical_formula_structural     'C4 H3 N3'
_chemical_formula_sum            'C4 H3 N3'
_chemical_formula_weight         93.09
_chemical_name_systematic
;
1H-Imidazole-4-carbonitrile
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.689(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7230(13)
_cell_length_b                   3.6965(9)
_cell_length_c                   10.244(2)
_cell_measurement_reflns_used    5074
_cell_measurement_temperature    158
_cell_measurement_theta_max      36.30
_cell_measurement_theta_min      4.01
_cell_volume                     214.76(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus '
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      158
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9453
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        36.31
_diffrn_reflns_theta_max         36.31
_diffrn_reflns_theta_min         4.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             96
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.185
_refine_ls_abs_structure_details
'merged for light atom structure, Mo radiation'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1011
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0315
_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)+(0.0589P)²+0.0007P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                977
_reflns_number_total             1011
_reflns_threshold_expression     I>2σ(I)
_[local]_cod_data_source_file    gh6011.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P c'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2205937
_cod_database_fobs_code          2205937
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,-y,1/2+z
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.34806(16) 0.4084(3) 0.80576(10) 0.02359(18) Uani d . 1 N
N2 0.90835(15) 0.0054(2) 1.15348(8) 0.01802(15) Uani d . 1 N
H2 0.970(7) -0.033(8) 1.230(2) 0.067(8) Uiso d D 1 H
N3 0.88969(13) 0.0210(2) 0.93560(8) 0.01742(15) Uani d . 1 N
C1 0.49911(15) 0.2985(2) 0.88149(9) 0.01763(16) Uani d . 1 C
C2 0.68577(14) 0.1638(2) 0.97403(8) 0.01497(14) Uani d . 1 C
C3 0.69551(16) 0.1552(2) 1.10900(9) 0.01745(16) Uani d . 1 C
H3 0.596(4) 0.222(5) 1.161(2) 0.030(5) Uiso d . 1 H
C4 1.01795(15) -0.0715(3) 1.04734(9) 0.01856(16) Uani d . 1 C
H4 1.172(4) -0.185(5) 1.049(2) 0.030(5) Uiso d . 1 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 0.0211(4) 0.0285(4) 0.0202(4) -0.0012(3) -0.0006(3) 0.0042(3)
N2 0.0211(3) 0.0229(3) 0.0095(3) -0.0019(2) -0.0002(2) 0.0009(2)
N3 0.0170(3) 0.0244(3) 0.0111(3) 0.0002(2) 0.0026(2) 0.0003(3)
C1 0.0189(3) 0.0203(3) 0.0138(3) -0.0017(3) 0.0024(2) 0.0011(3)
C2 0.0163(3) 0.0182(3) 0.0103(3) -0.0012(2) 0.0016(2) 0.0004(3)
C3 0.0212(4) 0.0210(3) 0.0106(3) -0.0011(3) 0.0036(2) -0.0005(3)
C4 0.0170(3) 0.0250(4) 0.0133(3) -0.0004(3) 0.0010(2) 0.0010(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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
C4 N2 C3 107.84(8)
C4 N2 H2 123(3)
C3 N2 H2 129(3)
C4 N3 C2 104.14(8)
N1 C1 C2 179.65(10)
C3 C2 N3 110.74(8)
C3 C2 C1 127.18(8)
N3 C2 C1 122.08(8)
N2 C3 C2 105.07(8)
N2 C3 H3 123.1(15)
C2 C3 H3 131.9(15)
N3 C4 N2 112.21(9)
N3 C4 H4 121.9(14)
N2 C4 H4 125.9(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.1553(13)
N2 C4 1.3561(13)
N2 C3 1.3600(14)
N2 H2 0.828(19)
N3 C4 1.3196(12)
N3 C2 1.3852(12)
C1 C2 1.4201(12)
C2 C3 1.3768(12)
C3 H3 0.86(2)
C4 H4 0.97(3)
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
N2 H2 N3 2 0.828(19) 2.21(3) 2.9080(12) 142(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
C4 N3 C2 C3 0.12(10)
C4 N3 C2 C1 179.76(8)
N1 C1 C2 C3 156(19)
N1 C1 C2 N3 -23(19)
C4 N2 C3 C2 -0.22(10)
N3 C2 C3 N2 0.06(10)
C1 C2 C3 N2 -179.56(9)
C2 N3 C4 N2 -0.27(11)
C3 N2 C4 N3 0.31(11)
