#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/57/2015760.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_2015760
loop_
_publ_author_name
'Costa, Marilia S.'
'Boechat, Nubia'
'Wardell, Solange M. S. V.'
'Ferreira, Vitor F.'
'Low, John N.'
'Glidewell, Christopher'
_publ_section_title
;
 Three ethyl 5-amino-1-aryl-1H-imidazole-4-carboxylates:
 hydrogen-bonded supramolecular structures in one, two and three
 dimensions
;
_journal_coeditor_code           SK3077
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o33
_journal_page_last               o37
_journal_paper_doi               10.1107/S0108270106048402
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H12 N4 O2'
_chemical_formula_moiety         'C13 H12 N4 O2'
_chemical_formula_sum            'C13 H12 N4 O2'
_chemical_formula_weight         256.27
_chemical_name_systematic
;
ethyl 5-amino-1-(4-cyanophenyl)-1H-imidazole-4-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.311(5)
_cell_angle_beta                 94.183(7)
_cell_angle_gamma                92.946(7)
_cell_formula_units_Z            2
_cell_length_a                   6.3212(5)
_cell_length_b                   9.4121(11)
_cell_length_c                   10.2496(12)
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      3.24
_cell_volume                     607.35(11)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11051
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0602
_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)+(0.0736P)²+0.0026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                1720
_reflns_number_total             2688
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3077.cif
_cod_data_source_block           I
_cod_database_code               2015760
_cod_database_fobs_code          2015760
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
O O41 0.2434(2) 0.01631(16) 0.69543(15) 0.0333(4) Uani d . 1
O O42 -0.0923(2) 0.08389(15) 0.70768(14) 0.0278(4) Uani d . 1
N N1 0.2612(2) 0.32789(18) 0.40492(17) 0.0239(4) Uani d . 1
N N3 -0.0421(3) 0.27643(18) 0.49852(18) 0.0268(4) Uani d . 1
N N5 0.4953(3) 0.16377(18) 0.51255(18) 0.0294(5) Uani d . 1
N N14 0.8987(3) 0.6796(2) -0.0046(2) 0.0411(5) Uani d . 1
C C2 0.0487(3) 0.3558(2) 0.4137(2) 0.0265(5) Uani d . 1
C C4 0.1169(3) 0.1903(2) 0.5512(2) 0.0242(5) Uani d . 1
C C5 0.3047(3) 0.2205(2) 0.4931(2) 0.0238(5) Uani d . 1
C C11 0.3986(3) 0.3979(2) 0.3183(2) 0.0237(5) Uani d . 1
C C12 0.3832(3) 0.5438(2) 0.3006(2) 0.0270(5) Uani d . 1
C C13 0.5118(3) 0.6140(2) 0.2157(2) 0.0296(5) Uani d . 1
C C14 0.6547(3) 0.5396(2) 0.1489(2) 0.0260(5) Uani d . 1
C C15 0.6686(3) 0.3932(2) 0.1663(2) 0.0276(5) Uani d . 1
C C16 0.5404(3) 0.3222(2) 0.2512(2) 0.0248(5) Uani d . 1
C C41 0.0973(3) 0.0889(2) 0.6555(2) 0.0257(5) Uani d . 1
C C42 -0.1120(3) -0.0169(2) 0.8145(2) 0.0298(5) Uani d . 1
C C43 -0.2963(3) 0.0227(2) 0.8891(2) 0.0330(6) Uani d . 1
C C141 0.7914(3) 0.6162(2) 0.0626(2) 0.0304(5) Uani d . 1
H H2 -0.0223 0.4255 0.3630 0.032 Uiso calc R 1
H H5A 0.4992 0.0963 0.5744 0.035 Uiso d R 1
H H5B 0.6148 0.2110 0.4906 0.035 Uiso d R 1
H H12 0.2852 0.5945 0.3464 0.032 Uiso calc R 1
H H13 0.5025 0.7135 0.2031 0.036 Uiso calc R 1
H H15 0.7660 0.3424 0.1200 0.033 Uiso calc R 1
H H16 0.5492 0.2227 0.2636 0.030 Uiso calc R 1
H H42A 0.0200 -0.0127 0.8730 0.036 Uiso calc R 1
H H42B -0.1364 -0.1150 0.7792 0.036 Uiso calc R 1
H H43A -0.2672 0.1178 0.9276 0.040 Uiso calc R 1
H H43B -0.3173 -0.0464 0.9587 0.040 Uiso calc R 1
H H43C -0.4249 0.0226 0.8295 0.040 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 0.0016 '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
_geom_angle_publ_flag
C5 N1 C2 106.30(16) no
C5 N1 C11 128.92(17) no
C2 N1 C11 124.77(17) no
C16 C11 C12 120.91(19) no
C16 C11 N1 121.00(18) no
C12 C11 N1 118.07(19) no
C13 C12 C11 119.4(2) no
C13 C12 H12 120.3 no
C11 C12 H12 120.3 no
C12 C13 C14 120.14(19) no
C12 C13 H13 119.9 no
C14 C13 H13 119.9 no
C13 C14 C15 120.30(18) no
C13 C14 C141 119.11(19) no
C15 C14 C141 120.59(19) no
N14 C141 C14 178.5(2) no
C16 C15 C14 119.9(2) no
C16 C15 H15 120.1 no
C14 C15 H15 120.1 no
C15 C16 C11 119.4(2) no
C15 C16 H16 120.3 no
C11 C16 H16 120.3 no
N5 C5 C4 130.44(19) no
N5 C5 N1 124.03(18) no
C4 C5 N1 105.53(17) no
N3 C2 N1 112.76(18) no
N3 C2 H2 123.6 no
N1 C2 H2 123.6 no
C2 N3 C4 105.25(16) no
C5 C4 N3 110.16(17) no
C5 C4 C41 123.32(18) no
N3 C4 C41 126.45(18) no
O41 C41 O42 122.79(19) no
O41 C41 C4 122.63(19) no
O42 C41 C4 114.55(17) no
C41 O42 C42 114.81(15) no
O42 C42 C43 107.95(17) no
O42 C42 H42A 110.1 no
C43 C42 H42A 110.1 no
O42 C42 H42B 110.1 no
C43 C42 H42B 110.1 no
H42A C42 H42B 108.4 no
C42 C43 H43A 109.5 no
C42 C43 H43B 109.5 no
H43A C43 H43B 109.5 no
C42 C43 H43C 109.5 no
H43A C43 H43C 109.5 no
H43B C43 H43C 109.5 no
C5 N5 H5A 113.5 no
C5 N5 H5B 121.3 no
H5A N5 H5B 121.2 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.384(3) no
N1 C2 1.391(2) no
N1 C11 1.427(3) no
C11 C16 1.391(3) no
C11 C12 1.394(3) no
C12 C13 1.381(3) no
C12 H12 0.95 no
C13 C14 1.388(3) no
C13 H13 0.95 no
C14 C15 1.397(3) no
C14 C141 1.450(3) no
C141 N14 1.150(3) no
C15 C16 1.383(3) no
C15 H15 0.95 no
C16 H16 0.95 no
C5 N5 1.345(3) no
C5 C4 1.384(3) no
C2 N3 1.295(3) no
C2 H2 0.95 no
N3 C4 1.403(2) no
C4 C41 1.445(3) no
C41 O41 1.225(2) no
C41 O42 1.346(2) no
O42 C42 1.461(2) no
C42 C43 1.500(3) no
C42 H42A 0.99 no
C42 H42B 0.99 no
C43 H43A 0.98 no
C43 H43B 0.98 no
C43 H43C 0.98 no
N5 H5A 0.90 no
N5 H5B 0.90 no
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
_geom_hbond_publ_flag
N5 H5A O41 . 0.90 2.21 2.866(2) 129 y
N5 H5B N3 1_655 0.90 2.22 3.073(2) 158 y
C15 H15 N14 2_765 0.95 2.52 3.397(3) 154 y
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
_geom_torsion_publ_flag
C5 N1 C11 C16 40.3(3) no
C2 N1 C11 C16 -138.4(2) no
C5 N1 C11 C12 -141.1(2) no
C2 N1 C11 C12 40.2(3) no
C16 C11 C12 C13 -0.4(3) no
N1 C11 C12 C13 -178.98(18) no
C11 C12 C13 C14 0.1(3) no
C12 C13 C14 C15 0.3(3) no
C12 C13 C14 C141 -178.6(2) no
C13 C14 C15 C16 -0.4(3) no
C141 C14 C15 C16 178.53(19) no
C14 C15 C16 C11 0.1(3) no
C12 C11 C16 C15 0.4(3) no
N1 C11 C16 C15 178.88(18) no
C2 N1 C5 N5 179.7(2) no
C11 N1 C5 N5 0.9(3) no
C2 N1 C5 C4 -0.5(2) no
C11 N1 C5 C4 -179.43(19) no
C5 N1 C2 N3 0.1(2) no
C11 N1 C2 N3 179.05(18) no
N1 C2 N3 C4 0.4(2) no
N5 C5 C4 N3 -179.5(2) no
N1 C5 C4 N3 0.8(2) no
N5 C5 C4 C41 3.4(4) no
N1 C5 C4 C41 -176.31(19) no
C2 N3 C4 C5 -0.7(2) no
C2 N3 C4 C41 176.3(2) no
C5 C4 C41 O41 -4.1(3) no
N3 C4 C41 O41 179.3(2) no
C5 C4 C41 O42 174.03(19) no
N3 C4 C41 O42 -2.6(3) no
O41 C41 O42 C42 -1.0(3) no
C4 C41 O42 C42 -179.12(18) no
C41 O42 C42 C43 161.84(18) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133311
