#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/17/2211707.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_2211707
loop_
_publ_author_name
'Aslantaş, Mehmet'
'Ceylan--Ünlüsoy, Meltem'
'Ertan, Rahmiye'
'Kendi, Engin'
'Büyükgüngör, Orhan'
_publ_section_title
;
 3-Ethyl-5-(4-oxochroman-3-ylmethylene)-1,3-imidazolidine-2,4-dione
;
_journal_coeditor_code           AT2183
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o184
_journal_page_last               o185
_journal_paper_doi               10.1107/S1600536806052378
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H12 N2 O4'
_chemical_formula_moiety         'C15 H12 N2 O4'
_chemical_formula_sum            'C15 H12 N2 O4'
_chemical_formula_weight         284.27
_chemical_name_systematic
;
3-Ethyl-5-(4-oxochroman-3-ylmethylene)-1,3-imidazolidine-2,4-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                106.953(6)
_cell_angle_beta                 101.066(6)
_cell_angle_gamma                92.143(6)
_cell_formula_units_Z            2
_cell_length_a                   5.3407(4)
_cell_length_b                   10.4070(8)
_cell_length_c                   12.0223(9)
_cell_measurement_reflns_used    9747
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      3.13
_cell_volume                     624.18(9)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9747
_diffrn_reflns_theta_full        28.5
_diffrn_reflns_theta_max         28.5
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32;  Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0598P)²+0.095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                2373
_reflns_number_total             3131
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2183.cif
_cod_data_source_block           I
_cod_database_code               2211707
_cod_database_fobs_code          2211707
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 O4 0.0983(2) 0.49490(11) -0.16132(9) 0.0264(2) Uani d . 1
H H1 0.497(4) 0.1214(18) 0.4248(17) 0.027(5) Uiso d . 1
H H10 0.179(4) 0.3843(18) 0.0156(16) 0.025(4) Uiso d . 1
H H11 0.668(4) 0.2149(19) -0.1303(17) 0.032(5) Uiso d . 1
O O1 0.3566(2) 0.23695(10) 0.27032(9) 0.0236(2) Uani d . 1
O O2 0.7307(2) 0.14083(11) -0.00515(9) 0.0259(2) Uani d . 1
O O3 0.6898(2) 0.25287(11) -0.33877(9) 0.0274(2) Uani d . 1
C C5 0.6738(3) 0.11573(13) 0.17631(12) 0.0204(3) Uani d . 1
N N2 0.3813(2) 0.39021(12) -0.27353(11) 0.0224(3) Uani d . 1
N N1 0.5705(2) 0.27450(12) -0.15918(11) 0.0223(3) Uani d . 1
C C13 0.5651(3) 0.29902(14) -0.26467(13) 0.0221(3) Uani d . 1
C C7 0.6140(3) 0.17199(13) 0.07652(12) 0.0199(3) Uani d . 1
C C12 0.2636(3) 0.41865(14) -0.17818(12) 0.0210(3) Uani d . 1
C C8 0.4109(3) 0.26248(13) 0.08340(12) 0.0198(3) Uani d . 1
C C9 0.2985(3) 0.28713(14) 0.17874(12) 0.0216(3) Uani d . 1
H H9 0.1686 0.3443 0.1807 0.026 Uiso calc R 1
C C14 0.3221(3) 0.44218(15) -0.37468(13) 0.0246(3) Uani d . 1
H H14A 0.4775 0.4531 -0.4029 0.03 Uiso calc R 1
H H14B 0.2606 0.5303 -0.3492 0.03 Uiso calc R 1
C C15 0.1211(3) 0.34943(15) -0.47615(13) 0.0272(3) Uani d . 1
H H15A 0.178 0.261 -0.4996 0.041 Uiso calc R 1
H H15B 0.0955 0.3846 -0.5425 0.041 Uiso calc R 1
H H15C -0.0375 0.3441 -0.4505 0.041 Uiso calc R 1
C C1 0.5904(3) 0.09625(15) 0.36340(13) 0.0253(3) Uani d . 1
C C11 0.3856(3) 0.33805(13) -0.10197(12) 0.0203(3) Uani d . 1
C C10 0.3145(3) 0.33350(14) -0.00244(12) 0.0206(3) Uani d . 1
C C6 0.5421(3) 0.14943(14) 0.26884(13) 0.0213(3) Uani d . 1
C C2 0.7731(3) 0.00679(15) 0.36424(13) 0.0263(3) Uani d . 1
H H2 0.8067 -0.0305 0.4264 0.032 Uiso calc R 1
C C4 0.8606(3) 0.02510(14) 0.18031(13) 0.0236(3) Uani d . 1
H H4 0.9519 0.0014 0.12 0.028 Uiso calc R 1
C C3 0.9093(3) -0.02900(15) 0.27333(14) 0.0264(3) Uani d . 1
H H3 1.0329 -0.0893 0.2755 0.032 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 0 '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 0.006 '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
C9 O1 C6 118.46(11) ?
C6 C5 C4 118.13(13) ?
C6 C5 C7 120.66(12) ?
C4 C5 C7 121.19(13) ?
C12 N2 C13 111.45(11) yes
C12 N2 C14 125.83(12) ?
C13 N2 C14 122.69(12) ?
C13 N1 C11 112.00(12) yes
C13 N1 H11 126.4(12) ?
C11 N1 H11 121.1(12) ?
O3 C13 N1 128.53(13) ?
O3 C13 N2 125.16(13) ?
N1 C13 N2 106.31(12) yes
O2 C7 C8 125.01(13) ?
O2 C7 C5 120.08(12) ?
C8 C7 C5 114.90(12) yes
O4 C12 N2 126.19(13) ?
O4 C12 C11 128.72(13) ?
N2 C12 C11 105.08(11) ?
C9 C8 C7 118.48(12) ?
C9 C8 C10 114.92(12) ?
C7 C8 C10 126.59(12) ?
O1 C9 C8 126.29(13) ?
O1 C9 H9 116.9 ?
C8 C9 H9 116.9 ?
N2 C14 C15 112.24(12) ?
N2 C14 H14A 109.2 ?
C15 C14 H14A 109.2 ?
N2 C14 H14B 109.2 ?
C15 C14 H14B 109.2 ?
H14A C14 H14B 107.9 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C2 C1 C6 118.26(14) ?
C2 C1 H1 121.9(11) ?
C6 C1 H1 119.9(11) ?
C10 C11 N1 131.50(13) ?
C10 C11 C12 123.50(13) ?
N1 C11 C12 104.99(12) ?
C11 C10 C8 131.40(13) yes
C11 C10 H10 114.4(11) ?
C8 C10 H10 114.2(11) ?
O1 C6 C1 116.61(13) ?
O1 C6 C5 121.19(12) yes
C1 C6 C5 122.20(13) ?
C1 C2 C3 121.13(14) ?
C1 C2 H2 119.4 ?
C3 C2 H2 119.4 ?
C3 C4 C5 120.24(14) ?
C3 C4 H4 119.9 ?
C5 C4 H4 119.9 ?
C4 C3 C2 120.02(14) ?
C4 C3 H3 120 ?
C2 C3 H3 120 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O4 C12 1.2151(17) yes
O1 C9 1.3407(17) yes
O1 C6 1.3698(16) yes
O2 C7 1.2336(17) yes
O3 C13 1.2121(18) yes
C5 C6 1.395(2) ?
C5 C4 1.4018(19) ?
C5 C7 1.4699(19) ?
N2 C12 1.3747(18) yes
N2 C13 1.4016(18) yes
N2 C14 1.4560(17) yes
N1 C13 1.3600(19) yes
N1 C11 1.3896(18) yes
N1 H11 0.92(2) ?
C7 C8 1.4614(19) yes
C12 C11 1.4925(19) ?
C8 C9 1.358(2) yes
C8 C10 1.4647(18) yes
C9 H9 0.93 ?
C14 C15 1.518(2) yes
C14 H14A 0.97 ?
C14 H14B 0.97 ?
C15 H15A 0.96 ?
C15 H15B 0.96 ?
C15 H15C 0.96 ?
C1 C2 1.374(2) ?
C1 C6 1.389(2) ?
C1 H1 0.949(19) ?
C11 C10 1.336(2) yes
C10 H10 0.936(19) ?
C2 C3 1.397(2) ?
C2 H2 0.93 ?
C4 C3 1.379(2) ?
C4 H4 0.93 ?
C3 H3 0.93 ?
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 H11 O2 1_555 0.93(2) 1.86(2) 2.6607(17) 142.9(18) yes
C10 H10 O4 1_555 0.93(2) 2.674(19) 2.995(2) 101.0(13) yes
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
C11 N1 C13 O3 -175.36(15) ?
C11 N1 C13 N2 4.25(16) ?
C12 N2 C13 O3 176.97(14) ?
C14 N2 C13 O3 -1.0(2) ?
C12 N2 C13 N1 -2.66(16) ?
C14 N2 C13 N1 179.33(13) yes
C6 C5 C7 O2 -179.56(13) ?
C4 C5 C7 O2 -0.8(2) ?
C6 C5 C7 C8 -0.20(19) ?
C4 C5 C7 C8 178.60(12) ?
C13 N2 C12 O4 179.37(14) ?
C14 N2 C12 O4 -2.7(2) ?
C13 N2 C12 C11 0.20(15) yes
C14 N2 C12 C11 178.14(13) ?
O2 C7 C8 C9 179.70(14) ?
C5 C7 C8 C9 0.38(18) ?
O2 C7 C8 C10 -1.4(2) ?
C5 C7 C8 C10 179.30(13) ?
C6 O1 C9 C8 -1.7(2) ?
C7 C8 C9 O1 0.6(2) ?
C10 C8 C9 O1 -178.44(13) ?
C12 N2 C14 C15 -91.48(17) ?
C13 N2 C14 C15 86.24(17) yes
C13 N1 C11 C10 174.91(15) ?
C13 N1 C11 C12 -4.09(16) ?
O4 C12 C11 C10 4.0(2) ?
N2 C12 C11 C10 -176.84(13) ?
O4 C12 C11 N1 -176.87(14) ?
N2 C12 C11 N1 2.26(14) ?
N1 C11 C10 C8 1.8(3) ?
C12 C11 C10 C8 -179.37(14) yes
C9 C8 C10 C11 176.85(15) ?
C7 C8 C10 C11 -2.1(2) yes
C9 O1 C6 C1 -177.89(13) ?
C9 O1 C6 C5 1.85(19) ?
C2 C1 C6 O1 179.24(12) ?
C2 C1 C6 C5 -0.5(2) ?
C4 C5 C6 O1 -179.76(12) yes
C7 C5 C6 O1 -0.9(2) ?
C4 C5 C6 C1 0.0(2) ?
C7 C5 C6 C1 178.80(13) ?
C6 C1 C2 C3 0.7(2) ?
C6 C5 C4 C3 0.4(2) ?
C7 C5 C4 C3 -178.43(13) ?
C5 C4 C3 C2 -0.2(2) ?
C1 C2 C3 C4 -0.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21178149
