#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/67/2226725.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_2226725
loop_
_publ_author_name
'Ali, Yousaf'
'Yu, Peng'
'Hua, Erbing'
'Rui, Guo'
'Qi, Sun'
_publ_section_title
;
 (E)-2-(2-Furylmethylidene)-2,3-dihydro-1H-pyrrolizin-1-one
;
_journal_coeditor_code           XU2760
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1578
_journal_paper_doi               10.1107/S1600536810017939
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H9 N O2'
_chemical_formula_moiety         'C12 H9 N O2'
_chemical_formula_sum            'C12 H9 N O2'
_chemical_formula_weight         199.20
_chemical_name_systematic
;
(E)-2-(2-Furylmethylidene)-2,3-dihydro-1H-pyrrolizin-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.157(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8170(16)
_cell_length_b                   6.1242(6)
_cell_length_c                   14.432(2)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.50
_cell_volume                     960.3(2)
_computing_cell_refinement       'CrystalClear (Rigaku, 2009)'
_computing_data_collection       'CrystalClear (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear (Rigaku, 2009)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD camera'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9348
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                1796
_reflns_number_total             2271
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu2760.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226725
_cod_database_fobs_code          2226725
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.81898(7) 0.03138(13) 0.87581(6) 0.0268(2) Uani d . 1 . .
O O2 1.15722(7) 0.60788(13) 0.91369(6) 0.0239(2) Uani d . 1 . .
N N1 0.76145(8) 0.52826(15) 0.74753(7) 0.0190(2) Uani d . 1 . .
C C1 0.82061(10) 0.21177(18) 0.83928(8) 0.0190(2) Uani d . 1 . .
C C2 0.71886(10) 0.33225(17) 0.76750(8) 0.0187(2) Uani d . 1 . .
C C3 0.59277(10) 0.32408(19) 0.71216(8) 0.0219(3) Uani d . 1 . .
H H3 0.5387 0.2083 0.7110 0.026 Uiso calc R 1 . .
C C4 0.56100(11) 0.52063(19) 0.65837(9) 0.0254(3) Uani d . 1 . .
H H4 0.4806 0.5618 0.6133 0.030 Uiso calc R 1 . .
C C5 0.66732(10) 0.64550(18) 0.68219(8) 0.0229(3) Uani d . 1 . .
H H5 0.6725 0.7869 0.6571 0.027 Uiso calc R 1 . .
C C6 0.89436(10) 0.56200(19) 0.80194(8) 0.0209(2) Uani d . 1 . .
H H6A 0.9119 0.6913 0.8466 0.025 Uiso calc R 1 . .
H H6B 0.9363 0.5784 0.7550 0.025 Uiso calc R 1 . .
C C7 0.93162(10) 0.35275(17) 0.86190(8) 0.0182(2) Uani d . 1 . .
C C8 1.04282(10) 0.29109(18) 0.92790(8) 0.0194(2) Uani d . 1 . .
H H8 1.0468 0.1525 0.9586 0.023 Uiso calc R 1 . .
C C9 1.15627(10) 0.40818(18) 0.95782(8) 0.0197(2) Uani d . 1 . .
C C10 1.27159(10) 0.35966(18) 1.02555(8) 0.0221(3) Uani d . 1 . .
H H10 1.2959 0.2323 1.0662 0.026 Uiso calc R 1 . .
C C11 1.34842(10) 0.5362(2) 1.02364(8) 0.0238(3) Uani d . 1 . .
H H11 1.4342 0.5499 1.0626 0.029 Uiso calc R 1 . .
C C12 1.27594(10) 0.6803(2) 0.95590(8) 0.0247(3) Uani d . 1 . .
H H12 1.3037 0.8148 0.9396 0.030 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
C12 O2 C9 . . 105.97(9) ?
C5 N1 C2 . . 110.01(9) ?
C5 N1 C6 . . 135.57(10) ?
C2 N1 C6 . . 114.42(9) ?
O1 C1 C2 . . 128.24(10) ?
O1 C1 C7 . . 125.91(10) ?
C2 C1 C7 . . 105.85(9) ?
N1 C2 C3 . . 108.03(9) ?
N1 C2 C1 . . 109.05(9) ?
C3 C2 C1 . . 142.91(10) ?
C2 C3 C4 . . 106.33(10) ?
C2 C3 H3 . . 126.8 ?
C4 C3 H3 . . 126.8 ?
C5 C4 C3 . . 108.40(10) ?
C5 C4 H4 . . 125.8 ?
C3 C4 H4 . . 125.8 ?
N1 C5 C4 . . 107.23(10) ?
N1 C5 H5 . . 126.4 ?
C4 C5 H5 . . 126.4 ?
N1 C6 C7 . . 101.32(8) ?
N1 C6 H6A . . 111.5 ?
C7 C6 H6A . . 111.5 ?
N1 C6 H6B . . 111.5 ?
C7 C6 H6B . . 111.5 ?
H6A C6 H6B . . 109.3 ?
C8 C7 C1 . . 121.59(10) ?
C8 C7 C6 . . 129.04(10) ?
C1 C7 C6 . . 109.36(9) ?
C7 C8 C9 . . 127.96(11) ?
C7 C8 H8 . . 116.0 ?
C9 C8 H8 . . 116.0 ?
C10 C9 O2 . . 109.70(10) ?
C10 C9 C8 . . 131.50(11) ?
O2 C9 C8 . . 118.80(9) ?
C9 C10 C11 . . 106.69(10) ?
C9 C10 H10 . . 126.7 ?
C11 C10 H10 . . 126.7 ?
C12 C11 C10 . . 106.53(10) ?
C12 C11 H11 . . 126.7 ?
C10 C11 H11 . . 126.7 ?
C11 C12 O2 . . 111.11(10) ?
C11 C12 H12 . . 124.4 ?
O2 C12 H12 . . 124.4 ?
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 C1 . 1.2274(13) ?
O2 C12 . 1.3652(14) ?
O2 C9 . 1.3810(13) ?
N1 C5 . 1.3480(14) ?
N1 C2 . 1.3754(14) ?
N1 C6 . 1.4683(14) ?
C1 C2 . 1.4435(14) ?
C1 C7 . 1.4953(15) ?
C2 C3 . 1.3873(15) ?
C3 C4 . 1.4011(15) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3935(17) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 C7 . 1.5117(14) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.3388(14) ?
C8 C9 . 1.4292(15) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.3613(15) ?
C10 C11 . 1.4191(16) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3451(17) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
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
C6 H6A O1 1_565 0.99 2.47 3.3076(15) 142
C8 H8 O1 3_757 0.95 2.55 3.3096(14) 137
C10 H10 O1 3_757 0.95 2.46 3.1789(15) 133
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 C3 . . . . 0.38(12) ?
C6 N1 C2 C3 . . . . 179.39(9) ?
C5 N1 C2 C1 . . . . -178.70(9) ?
C6 N1 C2 C1 . . . . 0.31(12) ?
O1 C1 C2 N1 . . . . 179.49(11) ?
C7 C1 C2 N1 . . . . -0.21(12) ?
O1 C1 C2 C3 . . . . 0.9(2) ?
C7 C1 C2 C3 . . . . -178.76(14) ?
N1 C2 C3 C4 . . . . 0.06(12) ?
C1 C2 C3 C4 . . . . 178.62(14) ?
C2 C3 C4 C5 . . . . -0.46(12) ?
C2 N1 C5 C4 . . . . -0.67(13) ?
C6 N1 C5 C4 . . . . -179.37(11) ?
C3 C4 C5 N1 . . . . 0.69(13) ?
C5 N1 C6 C7 . . . . 178.40(12) ?
C2 N1 C6 C7 . . . . -0.26(11) ?
O1 C1 C7 C8 . . . . -0.91(17) ?
C2 C1 C7 C8 . . . . 178.79(10) ?
O1 C1 C7 C6 . . . . -179.66(11) ?
C2 C1 C7 C6 . . . . 0.05(12) ?
N1 C6 C7 C8 . . . . -178.51(11) ?
N1 C6 C7 C1 . . . . 0.11(11) ?
C1 C7 C8 C9 . . . . -179.33(10) ?
C6 C7 C8 C9 . . . . -0.85(19) ?
C12 O2 C9 C10 . . . . 0.11(12) ?
C12 O2 C9 C8 . . . . -179.84(10) ?
C7 C8 C9 C10 . . . . 178.22(11) ?
C7 C8 C9 O2 . . . . -1.85(17) ?
O2 C9 C10 C11 . . . . -0.21(12) ?
C8 C9 C10 C11 . . . . 179.73(11) ?
C9 C10 C11 C12 . . . . 0.23(13) ?
C10 C11 C12 O2 . . . . -0.17(13) ?
C9 O2 C12 C11 . . . . 0.04(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745103
