#------------------------------------------------------------------------------
#$Date: 2016-06-23 04:16:30 +0300 (Thu, 23 Jun 2016) $
#$Revision: 183846 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/17/2241734.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_2241734
loop_
_publ_author_name
'Korkmaz, Ufuk'
'Bulut, Iclal'
'Bulut, Ahmet'
_publ_section_title
;
 Crystal structure of
 2-ethyl-4-methyl-1-(2-oxido-3,4-dioxocyclobut-1-en-1-yl)-1H-imidazol-3-ium
;
_journal_coeditor_code           XU5888
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              998
_journal_page_last               1001
_journal_paper_doi               10.1107/S2056989016009725
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C10 H10 N2 O3'
_chemical_formula_moiety         'C10 H10 N2 O3'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20
_chemical_melting_point          544
_chemical_name_systematic
2-Ethyl-4-methyl-1-(2-oxido-3,4-dioxocyclobut-1-en-1-yl)-1H-imidazol-3-ium
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.848(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7940(4)
_cell_length_b                   14.4120(9)
_cell_length_c                   14.5360(9)
_cell_measurement_reflns_used    943
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4374
_cell_measurement_theta_min      3.9785
_cell_volume                     1002.04(12)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2005)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0454
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Agilent SuperNova (single source at offset) Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5496
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_min         3.987
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1642
_refine_ls_R_factor_gt           0.0801
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0793P)²+0.4930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1840
_refine_ls_wR_factor_ref         0.2469
_reflns_number_gt                1363
_reflns_number_total             3048
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xu5888sup1.cif
_cod_data_source_block           I
_cod_database_code               2241734
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_occupancy
H H5 0.783(8) 0.546(3) 0.562(2) 0.060(11) Uiso d 1
H H1 0.312(8) 0.693(3) 0.724(2) 0.069(12) Uiso d 1
O O1 0.2719(5) 0.30379(16) 0.74162(16) 0.0548(7) Uani d 1
N N1 0.3883(6) 0.63979(19) 0.69274(18) 0.0419(6) Uani d 1
N N2 0.5210(5) 0.50284(17) 0.65685(16) 0.0382(6) Uani d 1
O O3 0.9453(5) 0.38166(18) 0.54799(18) 0.0614(7) Uani d 1
C C4 0.5674(6) 0.4072(2) 0.6522(2) 0.0375(7) Uani d 1
C C3 0.7687(7) 0.3595(2) 0.6001(2) 0.0432(8) Uani d 1
O O2 0.7096(6) 0.18740(16) 0.63047(19) 0.0675(8) Uani d 1
C C2 0.6603(7) 0.2691(2) 0.6374(2) 0.0454(8) Uani d 1
C C8 0.3574(6) 0.5506(2) 0.7126(2) 0.0393(7) Uani d 1
C C1 0.4553(7) 0.3249(2) 0.6897(2) 0.0409(7) Uani d 1
C C5 0.6580(7) 0.5660(2) 0.6024(2) 0.0415(7) Uani d 1
C C6 0.6446(9) 0.7446(2) 0.5893(2) 0.0590(10) Uani d 1
H H6A 0.5446 0.7912 0.6210 0.089 Uiso calc 1
H H6B 0.8420 0.7551 0.5998 0.089 Uiso calc 1
H H6C 0.5932 0.7479 0.5244 0.089 Uiso calc 1
C C9 0.1873(8) 0.5129(2) 0.7852(2) 0.0512(9) Uani d 1
H H9A 0.1038 0.4547 0.7641 0.061 Uiso calc 1
H H9B 0.0369 0.5559 0.7955 0.061 Uiso calc 1
C C7 0.5737(7) 0.6514(2) 0.6245(2) 0.0430(8) Uani d 1
C C10 0.3587(12) 0.4966(3) 0.8760(3) 0.0884(16) Uani d 1
H H10A 0.2398 0.4723 0.9208 0.133 Uiso calc 1
H H10B 0.5056 0.4531 0.8665 0.133 Uiso calc 1
H H10C 0.4387 0.5543 0.8979 0.133 Uiso calc 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
C8 N1 C7 111.0(3)
C8 N1 H1 127(2)
C7 N1 H1 121(2)
C8 N2 C5 108.7(3)
C8 N2 C4 129.1(3)
C5 N2 C4 122.1(3)
N2 C4 C1 137.4(3)
N2 C4 C3 127.6(3)
C1 C4 C3 95.0(3)
O3 C3 C4 136.1(3)
O3 C3 C2 135.9(3)
C2 C3 C4 88.0(2)
O2 C2 C1 134.2(3)
O2 C2 C3 137.3(3)
C1 C2 C3 88.5(2)
N1 C8 N2 106.5(3)
N1 C8 C9 125.8(3)
N2 C8 C9 127.6(3)
O1 C1 C4 137.8(3)
O1 C1 C2 133.6(3)
C2 C1 C4 88.6(2)
C7 C5 N2 107.6(3)
C7 C5 H5 132(2)
N2 C5 H5 121(2)
C7 C6 H6A 109.5
C7 C6 H6B 109.5
H6A C6 H6B 109.5
C7 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C9 C10 112.5(3)
C8 C9 H9A 109.1
C10 C9 H9A 109.1
C8 C9 H9B 109.1
C10 C9 H9B 109.1
H9A C9 H9B 107.8
C5 C7 N1 106.2(3)
C5 C7 C6 131.9(3)
N1 C7 C6 121.9(3)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.234(4) y
N1 C8 1.328(4) ?
N1 C7 1.386(4) ?
N1 H1 0.97(4) ?
C8 N2 1.353(4) y
N2 C5 1.399(4) ?
C4 N2 1.399(4) y
C3 O3 1.216(4) y
C1 C4 1.426(4) y
C3 C4 1.440(4) y
C2 C3 1.516(5) y
C2 O2 1.206(4) y
C1 C2 1.514(5) y
C8 C9 1.479(4) ?
C5 C7 1.341(4) y
C5 H5 0.91(4) ?
C6 C7 1.485(5) ?
C6 H6A 0.9600 ?
C6 H6B 0.9600 ?
C6 H6C 0.9600 ?
C9 C10 1.526(5) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 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 O1 2_556 0.97(4) 1.73(4) 2.680(3) 164(3)
C6 H6A O1 2_556 0.96 2.59 3.378(4) 139.1
C9 H9A O1 . 0.97 2.35 3.112(4) 134.9
C9 H9B O2 2_556 0.97 2.51 3.429(5) 157.5
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
C8 N2 C4 C1 8.9(6)
C5 N2 C4 C1 -173.9(3)
C8 N2 C4 C3 -171.7(3)
C5 N2 C4 C3 5.6(5)
N2 C4 C3 O3 -0.7(6)
C1 C4 C3 O3 178.9(4)
N2 C4 C3 C2 -179.7(3)
C1 C4 C3 C2 0.0(3)
O3 C3 C2 O2 1.2(7)
C4 C3 C2 O2 -179.8(4)
O3 C3 C2 C1 -179.0(4)
C4 C3 C2 C1 0.0(2)
C7 N1 C8 N2 -0.5(3)
C7 N1 C8 C9 176.7(3)
C5 N2 C8 N1 0.8(3)
C4 N2 C8 N1 178.3(3)
C5 N2 C8 C9 -176.3(3)
C4 N2 C8 C9 1.3(5)
N2 C4 C1 O1 0.0(7)
C3 C4 C1 O1 -179.5(4)
N2 C4 C1 C2 179.6(4)
C3 C4 C1 C2 0.0(3)
O2 C2 C1 O1 -0.6(7)
C3 C2 C1 O1 179.6(4)
O2 C2 C1 C4 179.8(4)
C3 C2 C1 C4 0.0(2)
C8 N2 C5 C7 -0.9(4)
C4 N2 C5 C7 -178.6(3)
N1 C8 C9 C10 -93.9(4)
N2 C8 C9 C10 82.6(4)
N2 C5 C7 N1 0.5(4)
N2 C5 C7 C6 -179.3(3)
C8 N1 C7 C5 -0.1(4)
C8 N1 C7 C6 179.8(3)

_cod_database_fobs_code 2241734
