#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227921.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227921
loop_
_publ_author_name
'Wang, Hong-Yong'
'Zou, Pei'
'Xie, Min-Hao'
'He, Yong-Jun'
'Wu, Jun'
_publ_section_title
;
 Ethyl 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetate
;
_journal_coeditor_code           PV2327
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2606
_journal_paper_doi               10.1107/S1600536810037098
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H11 N3 O4'
_chemical_formula_moiety         'C8 H11 N3 O4'
_chemical_formula_sum            'C8 H11 N3 O4'
_chemical_formula_weight         213.20
_chemical_name_systematic
;
Ethyl 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.416(3)
_cell_length_b                   10.290(6)
_cell_length_c                   20.769(12)
_cell_measurement_reflns_used    2529
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.55
_cell_volume                     943.8(10)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku SPIDER'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7883
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         3.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0331
_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)+(0.0463P)²+0.16P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0815
_reflns_number_gt                1161
_reflns_number_total             1306
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2327.cif
_cod_data_source_block           I
_cod_original_cell_volume        943.7(10)
_cod_database_code               2227921
_cod_database_fobs_code          2227921
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
O O1 0.3643(3) 0.58804(13) 0.42377(6) 0.0166(3) Uani d . 1 . .
O O2 0.7058(4) 0.74979(13) 0.42394(6) 0.0192(3) Uani d . 1 . .
O O3 1.0605(4) 0.80751(14) 0.14662(6) 0.0249(4) Uani d . 1 . .
O O4 1.1820(4) 1.00386(14) 0.17463(7) 0.0232(4) Uani d . 1 . .
N N1 0.5079(4) 0.82884(15) 0.30422(7) 0.0138(3) Uani d . 1 . .
N N2 0.7748(4) 1.00021(15) 0.27284(7) 0.0153(4) Uani d . 1 . .
N N3 1.0373(4) 0.90341(16) 0.18170(7) 0.0177(4) Uani d . 1 . .
C C1 0.6719(5) 0.78850(18) 0.25230(8) 0.0158(4) Uani d . 1 . .
H H1 0.6754 0.7046 0.2332 0.019 Uiso calc R 1 . .
C C2 0.8285(5) 0.89536(18) 0.23422(8) 0.0146(4) Uani d . 1 . .
C C3 0.5780(5) 0.95693(18) 0.31538(9) 0.0154(4) Uani d . 1 . .
C C4 0.4430(5) 1.03335(19) 0.36860(9) 0.0188(4) Uani d . 1 . .
H H4A 0.5425 1.1183 0.3711 0.023 Uiso calc R 1 . .
H H4B 0.4712 0.9868 0.4093 0.023 Uiso calc R 1 . .
H H4C 0.2262 1.0455 0.3606 0.023 Uiso calc R 1 . .
C C5 0.3162(5) 0.74537(19) 0.34314(8) 0.0163(4) Uani d . 1 . .
H H5A 0.2462 0.6708 0.3170 0.020 Uiso calc R 1 . .
H H5B 0.1357 0.7945 0.3576 0.020 Uiso calc R 1 . .
C C6 0.4893(5) 0.69604(18) 0.40139(8) 0.0155(4) Uani d . 1 . .
C C7 0.5214(5) 0.52893(19) 0.47784(9) 0.0200(4) Uani d . 1 . .
H H7A 0.4783 0.5775 0.5180 0.024 Uiso calc R 1 . .
H H7B 0.7428 0.5295 0.4704 0.024 Uiso calc R 1 . .
C C8 0.4071(6) 0.39131(19) 0.48318(10) 0.0237(5) Uani d . 1 . .
H H8A 0.1868 0.3921 0.4889 0.028 Uiso calc R 1 . .
H H8B 0.5021 0.3489 0.5203 0.028 Uiso calc R 1 . .
H H8C 0.4582 0.3435 0.4438 0.028 Uiso calc R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 C7 . . 115.04(16) ?
C1 N1 C3 . . 107.79(17) ?
C1 N1 C5 . . 124.75(16) ?
C3 N1 C5 . . 127.24(17) ?
C3 N2 C2 . . 103.97(16) ?
O4 N3 O3 . . 124.24(17) ?
O4 N3 C2 . . 118.48(16) ?
O3 N3 C2 . . 117.28(17) ?
C2 C1 N1 . . 104.11(16) ?
C2 C1 H1 . . 127.9 ?
N1 C1 H1 . . 127.9 ?
C1 C2 N2 . . 112.99(17) ?
C1 C2 N3 . . 126.05(17) ?
N2 C2 N3 . . 120.94(17) ?
N2 C3 N1 . . 111.11(17) ?
N2 C3 C4 . . 125.90(17) ?
N1 C3 C4 . . 122.98(18) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N1 C5 C6 . . 110.35(17) ?
N1 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
N1 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
O2 C6 O1 . . 125.57(18) ?
O2 C6 C5 . . 123.93(18) ?
O1 C6 C5 . . 110.49(17) ?
O1 C7 C8 . . 106.88(17) ?
O1 C7 H7A . . 110.3 ?
C8 C7 H7A . . 110.3 ?
O1 C7 H7B . . 110.3 ?
C8 C7 H7B . . 110.3 ?
H7A C7 H7B . . 108.6 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.325(2) ?
O1 C7 . 1.453(2) ?
O2 C6 . 1.199(2) ?
O3 N3 . 1.231(2) ?
O4 N3 . 1.224(2) ?
N1 C1 . 1.364(2) ?
N1 C3 . 1.374(2) ?
N1 C5 . 1.452(2) ?
N2 C3 . 1.317(3) ?
N2 C2 . 1.365(2) ?
N3 C2 . 1.431(2) ?
C1 C2 . 1.352(3) ?
C1 H1 . 0.9500 ?
C3 C4 . 1.482(3) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 C6 . 1.518(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C7 C8 . 1.507(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
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
C5 H5A O4 4_645 0.99 2.56 3.338(3) 135.4
C5 H5A N2 4_645 0.99 2.56 3.509(3) 160.4
C5 H5B O2 1_455 0.99 2.39 3.175(3) 135.6
C7 H7A O2 3_466 0.99 2.46 3.362(3) 150.5
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C1 C2 . . . . -1.0(2) ?
C5 N1 C1 C2 . . . . -176.05(18) ?
N1 C1 C2 N2 . . . . 1.0(2) ?
N1 C1 C2 N3 . . . . 179.56(18) ?
C3 N2 C2 C1 . . . . -0.6(2) ?
C3 N2 C2 N3 . . . . -179.20(17) ?
O4 N3 C2 C1 . . . . -173.7(2) ?
O3 N3 C2 C1 . . . . 5.9(3) ?
O4 N3 C2 N2 . . . . 4.7(3) ?
O3 N3 C2 N2 . . . . -175.69(18) ?
C2 N2 C3 N1 . . . . -0.1(2) ?
C2 N2 C3 C4 . . . . -179.70(19) ?
C1 N1 C3 N2 . . . . 0.8(2) ?
C5 N1 C3 N2 . . . . 175.61(18) ?
C1 N1 C3 C4 . . . . -179.65(18) ?
C5 N1 C3 C4 . . . . -4.8(3) ?
C1 N1 C5 C6 . . . . 94.6(2) ?
C3 N1 C5 C6 . . . . -79.4(2) ?
C7 O1 C6 O2 . . . . -3.9(3) ?
C7 O1 C6 C5 . . . . 177.17(16) ?
N1 C5 C6 O2 . . . . 23.4(3) ?
N1 C5 C6 O1 . . . . -157.72(16) ?
C6 O1 C7 C8 . . . . -163.26(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24028
