#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/55/2235546.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_2235546
loop_
_publ_author_name
'Tabatabaee, Masoumeh'
'Sharif, Mahboubeh A.'
'Dušek, Michal'
'Pojarová, Michaela'
_publ_section_title
;
 2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium chloride
;
_journal_coeditor_code           LH5487
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2183
_journal_page_last               o2184
_journal_paper_doi               10.1107/S1600536812027080
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C4 H8 N3 O +, Cl -'
_chemical_formula_moiety         'C4 H8 N3 O +, Cl -'
_chemical_formula_sum            'C4 H8 Cl N3 O'
_chemical_formula_weight         149.58
_chemical_name_systematic
;
2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium chloride
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.369(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4617(2)
_cell_length_b                   7.7073(2)
_cell_length_c                   10.2215(3)
_cell_measurement_reflns_used    5086
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      66.9352
_cell_measurement_theta_min      4.3685
_cell_volume                     659.52(3)
_computing_cell_refinement       'Crysalis CCD (Oxford Diffraction, 2007)'
_computing_data_collection       'Crysalis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'Crysalis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur Atlas Gemini ultra'
_diffrn_measurement_method
'Rotation method data acquisition using ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5373
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         6.35
_exptl_absorpt_coefficient_mu    4.505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.5648
_exptl_crystal_size_mid          0.3516
_exptl_crystal_size_min          0.1505
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0261
_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)+(0.0471P)²+0.1996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                1158
_reflns_number_total             1167
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5487.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2235546
_cod_database_fobs_code          2235546
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_symmetry_multiplicity
Cl Cl1 0.86814(3) 0.71590(4) 0.45236(3) 0.02046(16) Uani d . 1 1
O O1 0.43618(13) 0.57647(13) 0.32081(12) 0.0358(3) Uani d . 1 1
N N1 0.79940(13) 0.13245(15) 0.41934(11) 0.0238(3) Uani d . 1 1
H H1 0.8035 0.0210 0.4217 0.029 Uiso calc R 1 1
H H2 0.8847 0.1923 0.4421 0.029 Uiso calc R 1 1
N N2 0.64629(13) 0.38708(14) 0.37714(11) 0.0217(3) Uani d . 1 1
H H3 0.7227 0.4646 0.4031 0.026 Uiso d R 1 1
C C1 0.48933(16) 0.43236(18) 0.33205(13) 0.0234(3) Uani d . 1 1
C C2 0.40103(16) 0.26312(17) 0.30246(14) 0.0211(3) Uani d . 1 1
H H4 0.3128 0.2525 0.3529 0.025 Uiso calc R 1 1
H H5 0.3606 0.2526 0.2090 0.025 Uiso calc R 1 1
N N3 0.52395(13) 0.13463(14) 0.34360(11) 0.0189(3) Uani d . 1 1
C C3 0.66330(16) 0.21100(17) 0.38107(13) 0.0184(3) Uani d . 1 1
C C4 0.49578(15) -0.04876(17) 0.31667(13) 0.0222(3) Uani d . 1 1
H H6 0.4772 -0.0674 0.2228 0.027 Uiso calc R 1 1
H H7 0.4040 -0.0858 0.3545 0.027 Uiso calc R 1 1
H H8 0.5876 -0.1142 0.3549 0.027 Uiso calc R 1 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
Cl1 0.0170(2) 0.0197(2) 0.0238(2) -0.00117(10) 0.00001(14) -0.00029(10)
O1 0.0308(6) 0.0202(6) 0.0562(7) 0.0037(4) 0.0058(5) 0.0023(5)
N1 0.0176(6) 0.0207(6) 0.0312(6) -0.0022(4) -0.0029(5) -0.0001(5)
N2 0.0203(6) 0.0182(6) 0.0262(6) -0.0030(4) 0.0019(5) -0.0020(4)
C1 0.0225(7) 0.0205(7) 0.0279(7) 0.0009(5) 0.0055(5) 0.0006(5)
C2 0.0162(7) 0.0191(6) 0.0276(7) 0.0028(5) 0.0021(5) 0.0011(6)
N3 0.0166(5) 0.0163(6) 0.0233(6) -0.0002(4) 0.0007(4) 0.0001(4)
C3 0.0203(7) 0.0188(7) 0.0163(6) -0.0019(5) 0.0032(5) -0.0007(4)
C4 0.0195(7) 0.0175(6) 0.0285(7) -0.0017(5) 0.0002(5) -0.0008(5)
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'
Cl Cl 0.3639 0.7018 '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 H1 120.0
C3 N1 H2 120.0
H1 N1 H2 120.0
C3 N2 C1 110.62(11)
C3 N2 H3 126.1
C1 N2 H3 123.3
O1 C1 N2 126.44(13)
O1 C1 C2 127.82(12)
N2 C1 C2 105.73(11)
N3 C2 C1 102.59(11)
N3 C2 H4 111.2
C1 C2 H4 111.2
N3 C2 H5 111.2
C1 C2 H5 111.2
H4 C2 H5 109.2
C3 N3 C4 127.01(11)
C3 N3 C2 110.53(11)
C4 N3 C2 121.15(10)
N1 C3 N3 126.05(12)
N1 C3 N2 123.57(12)
N3 C3 N2 110.36(11)
N3 C4 H6 109.5
N3 C4 H7 109.5
H6 C4 H7 109.5
N3 C4 H8 109.5
H6 C4 H8 109.5
H7 C4 H8 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.1976(18)
N1 C3 1.3094(18)
N1 H1 0.8600
N1 H2 0.8600
N2 C3 1.3647(17)
N2 C1 1.3856(17)
N2 H3 0.8921
C1 C2 1.5118(19)
C2 N3 1.4533(16)
C2 H4 0.9700
C2 H5 0.9700
N3 C3 1.3237(18)
N3 C4 1.4530(17)
C4 H6 0.9600
C4 H7 0.9600
C4 H8 0.9600
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 Cl1 1_545 0.86 2.42 3.2714(12) 169
N1 H2 Cl1 3_766 0.86 2.32 3.1506(12) 163
N2 H3 Cl1 . 0.89 2.31 3.1808(11) 165
C2 H4 Cl1 3_666 0.97 2.69 3.6271(14) 162
C4 H8 Cl1 1_545 0.96 2.77 3.7241(13) 175
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 79367
