#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224388.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_2224388
loop_
_publ_author_name
'Wang, Shuai-Jun'
'Gu, Qiang'
'Su, Qing'
'Chen, Xiao-Dong'
'Zhang, Yu-Min'
_publ_section_title
;
 2,4,5-Tri-2-furyl-1H-imidazole
;
_journal_coeditor_code           OM2298
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3194
_journal_paper_doi               10.1107/S1600536809049514
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H10 N2 O3'
_chemical_formula_moiety         'C15 H10 N2 O3'
_chemical_formula_sum            'C15 H10 N2 O3'
_chemical_formula_weight         266.25
_chemical_name_systematic
;
2,4,5-Tri-2-furyl-1H-imidazole
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 116.29(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3940(19)
_cell_length_b                   17.146(3)
_cell_length_c                   9.1484(18)
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.44
_cell_volume                     1321.1(6)
_computing_cell_refinement       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω 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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6430
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1514
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0422
_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)+(0.0752P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                1089
_reflns_number_total             1514
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            om2298.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1321.1(5)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2224388
_cod_database_fobs_code          2224388
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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 0.2149(4) 0.03841(17) 0.1765(4) 0.0969(10) Uani d . 1 . .
O O2 0.2353(3) 0.22150(13) -0.1681(3) 0.0785(7) Uani d . 1 . .
O O3 0.7630(4) -0.05039(19) -0.0235(3) 0.0887(8) Uani d . 1 . .
N N1 0.4736(3) 0.01826(14) 0.1105(3) 0.0514(6) Uani d . 1 . .
H H1A 0.484(5) -0.016(2) 0.199(5) 0.071(10) Uiso d . 1 . .
N N2 0.5145(3) 0.06255(15) -0.0952(3) 0.0523(6) Uani d . 1 . .
C C1 0.1128(7) 0.0677(3) 0.2310(8) 0.1106(17) Uani d . 1 . .
H H1 0.0680 0.0389 0.2862 0.133 Uiso calc R 1 . .
C C2 0.0868(6) 0.1396(3) 0.1967(6) 0.0962(14) Uani d . 1 . .
H H2 0.0198 0.1716 0.2203 0.115 Uiso calc R 1 . .
C C3 0.1802(6) 0.1624(3) 0.1147(5) 0.0918(13) Uani d . 1 . .
H H3 0.1872 0.2118 0.0767 0.110 Uiso calc R 1 . .
C C4 0.2547(4) 0.09777(18) 0.1044(4) 0.0558(7) Uani d . 1 . .
C C5 0.3664(3) 0.07872(16) 0.0416(3) 0.0488(6) Uani d . 1 . .
C C6 0.3936(3) 0.10452(16) -0.0868(3) 0.0499(7) Uani d . 1 . .
C C7 0.3183(3) 0.16580(17) -0.2043(4) 0.0564(7) Uani d . 1 . .
C C8 0.3121(5) 0.1808(2) -0.3509(4) 0.0832(11) Uani d . 1 . .
H H8 0.3586 0.1518 -0.4043 0.100 Uiso calc R 1 . .
C C9 0.2190(5) 0.2505(3) -0.4089(6) 0.0884(13) Uani d . 1 . .
H H9 0.1935 0.2754 -0.5077 0.106 Uiso calc R 1 . .
C C10 0.1770(5) 0.2724(2) -0.2969(6) 0.0882(14) Uani d . 1 . .
H H10 0.1162 0.3162 -0.3035 0.106 Uiso calc R 1 . .
C C11 0.5600(3) 0.01121(16) 0.0265(3) 0.0492(6) Uani d . 1 . .
C C12 0.6862(4) -0.04443(19) 0.0694(4) 0.0588(8) Uani d . 1 . .
C C13 0.7492(5) -0.0938(2) 0.1934(5) 0.0807(12) Uani d . 1 . .
H H13 0.7166 -0.1013 0.2747 0.097 Uiso calc R 1 . .
C C14 0.8742(5) -0.1329(3) 0.1795(7) 0.0974(14) Uani d . 1 . .
H H14 0.9409 -0.1704 0.2501 0.117 Uiso calc R 1 . .
C C15 0.8781(6) -0.1061(3) 0.0482(7) 0.1003(15) Uani d . 1 . .
H H15 0.9489 -0.1224 0.0086 0.120 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C1 . . 107.1(3) ?
C7 O2 C10 . . 106.9(3) ?
C12 O3 C15 . . 106.3(4) ?
C11 N1 C5 . . 107.9(2) ?
C11 N1 H1A . . 124(2) ?
C5 N1 H1A . . 128(2) ?
C11 N2 C6 . . 105.5(2) ?
C2 C1 O1 . . 111.0(4) ?
C2 C1 H1 . . 124.5 ?
O1 C1 H1 . . 124.5 ?
C1 C2 C3 . . 107.4(4) ?
C1 C2 H2 . . 126.3 ?
C3 C2 H2 . . 126.3 ?
C4 C3 C2 . . 105.7(4) ?
C4 C3 H3 . . 127.1 ?
C2 C3 H3 . . 127.1 ?
C3 C4 O1 . . 108.9(3) ?
C3 C4 C5 . . 135.5(3) ?
O1 C4 C5 . . 115.6(3) ?
C6 C5 N1 . . 104.8(3) ?
C6 C5 C4 . . 135.2(3) ?
N1 C5 C4 . . 119.9(3) ?
N2 C6 C5 . . 110.4(2) ?
N2 C6 C7 . . 118.9(3) ?
C5 C6 C7 . . 130.7(3) ?
C8 C7 O2 . . 109.4(3) ?
C8 C7 C6 . . 132.3(3) ?
O2 C7 C6 . . 118.2(3) ?
C7 C8 C9 . . 106.2(4) ?
C7 C8 H8 . . 126.9 ?
C9 C8 H8 . . 126.9 ?
C10 C9 C8 . . 107.2(3) ?
C10 C9 H9 . . 126.4 ?
C8 C9 H9 . . 126.4 ?
C9 C10 O2 . . 110.3(4) ?
C9 C10 H10 . . 124.8 ?
O2 C10 H10 . . 124.8 ?
N2 C11 N1 . . 111.4(2) ?
N2 C11 C12 . . 126.1(3) ?
N1 C11 C12 . . 122.5(2) ?
C13 C12 O3 . . 109.4(3) ?
C13 C12 C11 . . 131.3(3) ?
O3 C12 C11 . . 119.3(3) ?
C12 C13 C14 . . 107.5(4) ?
C12 C13 H13 . . 126.2 ?
C14 C13 H13 . . 126.2 ?
C15 C14 C13 . . 106.3(4) ?
C15 C14 H14 . . 126.8 ?
C13 C14 H14 . . 126.8 ?
C14 C15 O3 . . 110.4(4) ?
C14 C15 H15 . . 124.8 ?
O3 C15 H15 . . 124.8 ?
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 C4 . 1.352(4) ?
O1 C1 . 1.358(5) ?
O2 C7 . 1.363(4) ?
O2 C10 . 1.370(4) ?
O3 C12 . 1.340(4) ?
O3 C15 . 1.373(6) ?
N1 C11 . 1.349(4) ?
N1 C5 . 1.387(4) ?
N1 H1A . 0.96(4) ?
N2 C11 . 1.332(4) ?
N2 C6 . 1.375(4) ?
C1 C2 . 1.269(7) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.438(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.336(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.440(4) ?
C5 C6 . 1.381(4) ?
C6 C7 . 1.444(4) ?
C7 C8 . 1.341(5) ?
C8 C9 . 1.437(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.306(7) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.434(4) ?
C12 C13 . 1.326(5) ?
C13 C14 . 1.406(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.302(7) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
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
N1 H1A N2 2 0.97(3) 1.94(3) 2.899(3) 167(2) y
C10 H10 Cg 4_454 0.93 2.8106(6) 3.603(3) 143.807(19) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743936
