#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020876.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_4020876
loop_
_publ_author_name
'Chia-Hui Chien'
'Man-kit Leung'
'Jen-Kuan Su'
'Gene-Hsiang Li'
'Yi-Hung Liu'
'Yu Wang'
_publ_section_title
;
 Substituent Effects on Pyrid-2-yl Ureas toward Intramolecular
 Hydrogen Bonding and Cytosine Complexation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1866
_journal_page_last               1871
_journal_paper_doi               10.1021/jo0355808
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C12 H13 I N4 O'
_chemical_formula_weight         356.16
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.056(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8157(11)
_cell_length_b                   8.0795(8)
_cell_length_c                   14.0426(13)
_cell_measurement_temperature    150(2)
_cell_volume                     1305.9(2)
_diffrn_ambient_temperature      150(2)
_exptl_crystal_density_diffrn    1.812
_refine_ls_R_factor_obs          0.0131
_refine_ls_wR_factor_obs         0.0332
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4020876
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
I1 I 0.596384(10) 0.28111(2) 0.234412(8) 0.02544(6) Uani 1 d . .
O1 O 1.05150(11) 0.2157(2) 0.10981(9) 0.0287(3) Uani 1 d . .
N1 N 0.96261(13) 0.2723(2) -0.04986(11) 0.0220(3) Uani 1 d . .
H1A H 0.96899(13) 0.2535(2) -0.11014(11) 0.026 Uiso 1 calc R .
N2 N 1.12913(12) 0.1201(2) -0.01604(10) 0.0213(3) Uani 1 d . .
H2A H 1.11595(12) 0.1153(2) -0.08021(10) 0.026 Uiso 1 calc R .
N3 N 0.79763(13) 0.4074(2) -0.12569(11) 0.0254(3) Uani 1 d . .
N4 N 1.42789(12) -0.1264(2) 0.12408(10) 0.0217(3) Uani 1 d . .
C1 C 1.04745(15) 0.2055(2) 0.02277(13) 0.0202(4) Uani 1 d . .
C2 C 0.86647(15) 0.3674(2) -0.03948(13) 0.0199(4) Uani 1 d . .
C3 C 0.8449(2) 0.4156(2) 0.04984(13) 0.0239(4) Uani 1 d . .
H3B H 0.8968(2) 0.3868(2) 0.10963(13) 0.029 Uiso 1 calc R .
C4 C 0.7456(2) 0.5066(2) 0.04899(14) 0.0263(4) Uani 1 d . .
H4A H 0.7277(2) 0.5405(2) 0.10870(14) 0.032 Uiso 1 calc R .
C5 C 0.6723(2) 0.5481(2) -0.03942(14) 0.0275(4) Uani 1 d . .
H5A H 0.6032(2) 0.6096(2) -0.04170(14) 0.033 Uiso 1 calc R .
C6 C 0.7026(2) 0.4976(2) -0.12393(14) 0.0288(4) Uani 1 d . .
H6A H 0.6534(2) 0.5283(2) -0.18463(14) 0.035 Uiso 1 calc R .
C7 C 1.22785(14) 0.0427(2) 0.03470(12) 0.0194(4) Uani 1 d . .
C8 C 1.2949(2) -0.0432(2) -0.02039(13) 0.0218(4) Uani 1 d . .
H8A H 1.2719(2) -0.0438(2) -0.08974(13) 0.026 Uiso 1 calc R .
C9 C 1.3927(2) -0.1255(2) 0.02572(13) 0.0230(4) Uani 1 d . .
H9A H 1.4371(2) -0.1833(2) -0.01218(13) 0.028 Uiso 1 calc R .
C10 C 1.3659(2) -0.0428(2) 0.17803(13) 0.0235(4) Uani 1 d . .
H10A H 1.3919(2) -0.0429(2) 0.24718(13) 0.028 Uiso 1 calc R .
C11 C 1.2670(2) 0.0420(2) 0.13660(12) 0.0222(4) Uani 1 d . .
H11A H 1.2252(2) 0.1000(2) 0.17652(12) 0.027 Uiso 1 calc R .
C12 C 1.5349(2) -0.2153(3) 0.17294(15) 0.0309(4) Uani 1 d . .
H12A H 1.5691(2) -0.2692(3) 0.12358(15) 0.046 Uiso 1 calc R .
H12B H 1.5156(2) -0.2991(3) 0.21719(15) 0.046 Uiso 1 calc R .
H12C H 1.5906(2) -0.1364(3) 0.21038(15) 0.046 Uiso 1 calc R .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.215(2) . ?
N1 C1 1.369(2) . ?
N1 C2 1.406(2) . ?
N2 C7 1.373(2) . ?
N2 C1 1.394(2) . ?
N3 C2 1.337(2) . ?
N3 C6 1.343(2) . ?
N4 C10 1.348(2) . ?
N4 C9 1.349(2) . ?
N4 C12 1.480(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.382(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.377(3) . ?
C7 C11 1.401(2) . ?
C7 C8 1.409(2) . ?
C8 C9 1.364(3) . ?
C10 C11 1.366(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21155377
2 PubChem 12099955
