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#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/14/2001414.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_2001414
loop_
_publ_author_name
'Booth, B. L.'
'Pritchard, R. G.'
'Freitas, A. P.'
'Proença, M. F. J. R. P.'
_publ_section_title
;
 Ethyl 3-(5-amino-4-cyano-1-imidazolyl-amino)-2-butenoate: an example
 of a combined inter- and intramolecular bifurcated hydrogen bond
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1695
_journal_page_last               1696
_journal_paper_doi               10.1107/S0108270193002938
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C10 H13 N5 O2'
_chemical_formula_sum            'C10 H13 N5 O2'
_chemical_formula_weight         235.24
_chemical_name_systematic
;
 Ethyl 3-(5-amino-4-cyano-1-imidazolylamino)but-2-enoate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 108.66(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.619(5)
_cell_length_b                   14.587(8)
_cell_length_c                   12.024(4)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.93
_cell_measurement_theta_min      14.49
_cell_volume                     2429.3(18)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'TEXSAN PROCESS (MSC, 1985)'
_computing_molecular_graphics    'PLUTO (Motherwell & Clegg, 1978)'
_computing_publication_material
'TEXSAN FINISH (MSC, 1985). Literature survey: CSSR (1984).'
_computing_structure_refinement  'TEXSAN LS (MSC, 1985)'
_computing_structure_solution    'TEXSAN MITHRIL (Gilmore, 1984)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       AFC-6S
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2305
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.0
_diffrn_standards_decay_%        -1.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.0881
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       rods
_exptl_crystal_F_000             992.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         -0.22802
_refine_diff_density_min         0.10781
_refine_ls_extinction_method     'not applied'
_refine_ls_goodness_of_fit_obs   1.448
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         1041
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0376
_refine_ls_shift/esd_max         0.0119
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0410
_reflns_number_observed          1041
_reflns_number_total             2210
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            al1047.cif
_cod_data_source_block           al1047_structure_1_of_1
_cod_original_cell_volume        2429.0(10)
_cod_original_sg_symbol_H-M      'C 2/c                  '
_cod_database_code               2001414
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y,1/2-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2-y,-z
1/2-x,1/2+y,1/2-z
1/2+x,1/2-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
N1 0.3332(2) 0.0345(2) 0.1326(2) 0.0451
C2 0.3523(3) 0.0062(3) 0.2462(3) 0.0550
N3 0.2755(2) -0.0239(2) 0.2654(2) 0.0560
C4 0.2023(2) -0.0136(2) 0.1587(3) 0.0446
C5 0.2366(2) 0.0229(2) 0.0749(3) 0.0406
N6 0.3978(2) 0.0794(2) 0.0880(2) 0.0472
C7 0.1046(3) -0.0365(3) 0.1438(3) 0.0523
N8 0.0256(2) -0.0534(3) 0.1297(3) 0.0756
N9 0.1951(2) 0.0493(2) -0.0370(2) 0.0523
C11 0.5176(2) 0.1769(3) -0.0213(3) 0.0544
C12 0.4595(3) 0.2186(3) 0.0404(3) 0.0608
C13 0.4037(2) 0.1724(2) 0.0908(3) 0.0468
C14 0.3464(3) 0.2219(3) 0.1560(4) 0.0665
O15 0.5637(2) 0.2409(2) -0.0645(2) 0.0821
O16 0.5260(2) 0.0955(2) -0.0354(2) 0.0572
C17 0.6245(4) 0.2079(3) -0.1305(5) 0.0937
C18 0.6557(7) 0.2923(6) -0.1811(9) 0.1384
H2 0.418(2) 0.008(2) 0.305(3) 0.064(9)
H6 0.421(2) 0.044(2) 0.047(3) 0.053(10)
H9A 0.229(2) 0.048(2) -0.086(3) 0.062(10)
H9B 0.130(3) 0.037(2) -0.071(3) 0.070(10)
H12 0.463(2) 0.283(2) 0.052(3) 0.058(10)
H14A 0.285(3) 0.208(3) 0.122(3) 0.090(10)
H14B 0.363(2) 0.194(3) 0.239(3) 0.090(10)
H14C 0.358(2) 0.286(3) 0.159(3) 0.080(10)
H17A 0.586(3) 0.168(3) -0.191(3) 0.090(10)
H17B 0.681(3) 0.171(4) -0.067(4) 0.15(2)
H18A 0.695(4) 0.330(4) -0.119(5) 0.15(2)
H18B 0.699(4) 0.273(4) -0.215(4) 0.13(2)
H18C 0.606(4) 0.324(5) -0.229(6) 0.18(3)
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 -2
-2 2 4
-4 2 -2
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . . 108.4(2) yes
C2 N1 N6 . . . 125.5(3) yes
C5 N1 N6 . . . 125.5(2) yes
N3 C4 C7 . . . 122.5(3) yes
N1 C5 C4 . . . 103.7(2) yes
N1 N6 C13 . . . 120.4(3) yes
C12 C11 O15 . . . 111.0(3) yes
C11 C12 C13 . . . 124.6(3) yes
N6 C13 C12 . . . 122.1(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . . 1.368(4) yes
N1 C5 . . 1.370(3) yes
N1 N6 . . 1.390(3) yes
C2 N3 . . 1.294(4) yes
N3 C4 . . 1.391(4) yes
C4 C5 . . 1.369(4) yes
C5 N9 . . 1.343(4) yes
N6 C13 . . 1.360(4) yes
C11 C12 . . 1.430(5) yes
C11 O15 . . 1.349(4) yes
C11 O16 . . 1.211(4) yes
C12 C13 . . 1.343(4) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139053776
