#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/83/2238338.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_2238338
loop_
_publ_author_name
'Kalkhambkar, Rajesh G.'
'Kumar, Mahesh'
'Gayathri, D.'
'Oh, Jeongsu'
'Jeong, Yeon Tae'
_publ_section_title
;
 (Z)-Ethyl 2-cyano-3-(1H-imidazol-2-yl)acrylate
;
_journal_coeditor_code           FJ2635
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1223
_journal_paper_doi               10.1107/S1600536813018278
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C9 H9 N3 O2'
_chemical_formula_moiety         'C9 H9 N3 O2'
_chemical_formula_sum            'C9 H9 N3 O2'
_chemical_formula_weight         191.19
_chemical_name_systematic
;
(Z)-Ethyl 2-cyano-3-(1H-imidazol-2-yl)acrylate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 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                   10.0768(7)
_cell_length_b                   12.0387(8)
_cell_length_c                   7.7047(6)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.636
_cell_volume                     934.67(12)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7118
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1436
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0486
_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)+(0.1215P)²+0.1600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                1189
_reflns_number_total             1436
_reflns_threshold_expression     (>2sigma(I)
_cod_data_source_file            fj2635.cif
_cod_data_source_block           I
_cod_database_code               2238338
_cod_database_fobs_code          2238338
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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
C C1 0.1765(3) -0.1284(2) -0.3293(4) 0.0457(6) Uani d . 1 1
H H1 0.1447 -0.1956 -0.3719 0.055 Uiso calc R 1 1
C C2 0.3054(2) -0.0942(2) -0.3241(4) 0.0447(6) Uani d . 1 1
H H2 0.3770 -0.1355 -0.3647 0.054 Uiso calc R 1 1
C C3 0.1905(2) 0.03689(18) -0.2134(3) 0.0364(5) Uani d . 1 1
C C4 0.1407(2) 0.13759(19) -0.1392(4) 0.0394(5) Uani d . 1 1
H H4 0.0487 0.1416 -0.1308 0.047 Uiso calc R 1 1
C C5 0.20598(19) 0.22724(19) -0.0798(4) 0.0366(4) Uani d . 1 1
C C6 0.1238(2) 0.32086(19) -0.0127(4) 0.0416(5) Uani d . 1 1
C C7 0.1271(3) 0.4938(2) 0.1330(5) 0.0623(9) Uani d . 1 1
H H7A 0.0624 0.5220 0.0509 0.075 Uiso calc R 1 1
H H7B 0.0806 0.4701 0.2368 0.075 Uiso calc R 1 1
C C8 0.2242(4) 0.5808(3) 0.1760(6) 0.0696(10) Uani d . 1 1
H H8A 0.2917 0.5503 0.2499 0.104 Uiso calc R 1 1
H H8B 0.1802 0.6406 0.2350 0.104 Uiso calc R 1 1
H H8C 0.2641 0.6082 0.0713 0.104 Uiso calc R 1 1
C C9 0.3471(2) 0.23680(19) -0.0740(4) 0.0421(5) Uani d . 1 1
N N1 0.10482(18) -0.04511(16) -0.2601(3) 0.0420(5) Uani d . 1 1
H H1A 0.0200 -0.0440 -0.2477 0.050 Uiso calc R 1 1
N N2 0.31525(19) 0.00888(17) -0.2512(3) 0.0396(5) Uani d . 1 1
N N3 0.4589(2) 0.2480(2) -0.0668(5) 0.0642(8) Uani d . 1 1
O O1 0.00530(18) 0.32337(16) -0.0221(4) 0.0626(7) Uani d . 1 1
O O2 0.19908(17) 0.40053(15) 0.0574(3) 0.0515(5) Uani d . 1 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
N1 C1 C2 105.9(2)
N1 C1 H1 127.0
C2 C1 H1 127.0
N2 C2 C1 110.8(2)
N2 C2 H2 124.6
C1 C2 H2 124.6
N2 C3 N1 110.9(2)
N2 C3 C4 129.2(2)
N1 C3 C4 119.9(2)
C5 C4 C3 130.1(2)
C5 C4 H4 114.9
C3 C4 H4 114.9
C4 C5 C9 124.3(2)
C4 C5 C6 116.95(19)
C9 C5 C6 118.8(2)
O1 C6 O2 124.9(2)
O1 C6 C5 123.5(2)
O2 C6 C5 111.56(19)
C8 C7 O2 107.9(3)
C8 C7 H7A 110.1
O2 C7 H7A 110.1
C8 C7 H7B 110.1
O2 C7 H7B 110.1
H7A C7 H7B 108.4
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
N3 C9 C5 177.6(3)
C1 N1 C3 107.74(18)
C1 N1 H1A 126.1
C3 N1 H1A 126.1
C3 N2 C2 104.54(19)
C6 O2 C7 115.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.346(3)
C1 C2 1.363(3)
C1 H1 0.9300
C2 N2 1.366(3)
C2 H2 0.9300
C3 N2 1.334(3)
C3 N1 1.360(3)
C3 C4 1.431(3)
C4 C5 1.344(3)
C4 H4 0.9300
C5 C9 1.428(3)
C5 C6 1.491(3)
C6 O1 1.197(3)
C6 O2 1.337(3)
C7 C8 1.472(5)
C7 O2 1.458(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 N3 1.135(3)
N1 H1A 0.8600
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
C4 H4 O1 . 0.93 2.38 2.771(3) 105
N1 H1A N2 4_455 0.86 2.11 2.951(3) 167
C1 H1 O1 2_554 0.93 2.45 3.328(4) 158
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
N1 C1 C2 N2 0.6(4)
N2 C3 C4 C5 -4.1(5)
N1 C3 C4 C5 177.9(3)
C3 C4 C5 C9 -2.6(5)
C3 C4 C5 C6 178.8(3)
C4 C5 C6 O1 -6.1(5)
C9 C5 C6 O1 175.1(3)
C4 C5 C6 O2 174.2(3)
C9 C5 C6 O2 -4.5(4)
C2 C1 N1 C3 -0.5(3)
N2 C3 N1 C1 0.2(3)
C4 C3 N1 C1 178.6(3)
N1 C3 N2 C2 0.1(3)
C4 C3 N2 C2 -178.1(3)
C1 C2 N2 C3 -0.4(3)
O1 C6 O2 C7 2.7(5)
C5 C6 O2 C7 -177.6(3)
C8 C7 O2 C6 -170.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139085829
