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#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/71/2227176.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_2227176
loop_
_publ_author_name
'Ali, Yousaf'
'Peng, Yu'
'Hua, Erbing'
'Anwar, Mohammad Aijaz'
'Kalhoro, Mehboob Ali'
_publ_section_title
;
 2,3-Dihydro-1H-pyrrolizin-1-one
;
_journal_coeditor_code           BQ2209
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2612
_journal_paper_doi               10.1107/S1600536810034902
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H7 N O'
_chemical_formula_moiety         'C7 H7 N O'
_chemical_formula_sum            'C7 H7 N O'
_chemical_formula_weight         121.14
_chemical_melting_point          327.0(10)
_chemical_name_systematic
;
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                 90.989(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3010(10)
_cell_length_b                   7.1730(7)
_cell_length_c                   14.3760(16)
_cell_measurement_reflns_used    3403
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      1.80
_cell_volume                     1165.2(2)
_computing_cell_refinement       'CrystalClear-SM Expert (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert (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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10183
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear-SM Expert; Rigaku, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0568
_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)+(0.0430P)²+0.3505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                2003
_reflns_number_total             2284
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2209.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227176
_cod_database_fobs_code          2227176
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 0.84120(12) 0.0832(2) 0.57308(9) 0.0293(4) Uani d . 1 . .
O O2 0.49964(11) 0.0828(2) 0.17318(10) 0.0329(4) Uani d . 1 . .
N N1 0.72173(13) 0.1521(2) 0.35032(11) 0.0181(4) Uani d . 1 . .
N N2 0.20229(13) 0.1557(2) 0.11650(11) 0.0190(4) Uani d . 1 . .
C C1 0.78107(17) 0.0987(3) 0.50200(13) 0.0214(4) Uani d . 1 . .
C C2 0.64640(16) 0.0776(3) 0.49734(13) 0.0229(5) Uani d . 1 . .
H H2A 0.6086 0.1646 0.5413 0.027 Uiso calc R 1 . .
H H2B 0.6233 -0.0513 0.5136 0.027 Uiso calc R 1 . .
C C3 0.60795(16) 0.1231(3) 0.39650(13) 0.0222(4) Uani d . 1 . .
H H3A 0.5634 0.0183 0.3680 0.027 Uiso calc R 1 . .
H H3B 0.5586 0.2371 0.3938 0.027 Uiso calc R 1 . .
C C4 0.81910(16) 0.1386(3) 0.40853(13) 0.0186(4) Uani d . 1 . .
C C5 0.91883(17) 0.1737(3) 0.35603(13) 0.0226(4) Uani d . 1 . .
H H5 0.9988 0.1728 0.3775 0.027 Uiso calc R 1 . .
C C6 0.87834(16) 0.2109(3) 0.26502(13) 0.0218(4) Uani d . 1 . .
H H6 0.9265 0.2405 0.2136 0.026 Uiso calc R 1 . .
C C7 0.75535(16) 0.1968(3) 0.26317(13) 0.0209(4) Uani d . 1 . .
H H7 0.7046 0.2152 0.2106 0.025 Uiso calc R 1 . .
C C8 0.39292(16) 0.1181(3) 0.16955(14) 0.0219(4) Uani d . 1 . .
C C9 0.32016(16) 0.1840(3) 0.25181(13) 0.0223(4) Uani d . 1 . .
H H9A 0.3490 0.3065 0.2743 0.027 Uiso calc R 1 . .
H H9B 0.3260 0.0934 0.3036 0.027 Uiso calc R 1 . .
C C10 0.19132(16) 0.1993(3) 0.21584(13) 0.0208(4) Uani d . 1 . .
H H10A 0.1395 0.1084 0.2472 0.025 Uiso calc R 1 . .
H H10B 0.1596 0.3265 0.2250 0.025 Uiso calc R 1 . .
C C11 0.31432(15) 0.1065(3) 0.09001(13) 0.0186(4) Uani d . 1 . .
C C12 0.30999(17) 0.0643(3) -0.00456(14) 0.0223(4) Uani d . 1 . .
H H12 0.3741 0.0258 -0.0419 0.027 Uiso calc R 1 . .
C C13 0.19207(17) 0.0901(3) -0.03344(14) 0.0239(5) Uani d . 1 . .
H H13 0.1615 0.0721 -0.0948 0.029 Uiso calc R 1 . .
C C14 0.12721(17) 0.1468(3) 0.04322(14) 0.0238(5) Uani d . 1 . .
H H14 0.0450 0.1741 0.0435 0.029 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
C7 N1 C4 . . 110.21(16) ?
C7 N1 C3 . . 135.39(16) ?
C4 N1 C3 . . 114.33(15) ?
C14 N2 C11 . . 110.07(16) ?
C14 N2 C10 . . 135.23(16) ?
C11 N2 C10 . . 114.68(15) ?
O1 C1 C4 . . 128.66(18) ?
O1 C1 C2 . . 124.46(18) ?
C4 C1 C2 . . 106.88(16) ?
C1 C2 C3 . . 106.52(15) ?
C1 C2 H2A . . 110.4 ?
C3 C2 H2A . . 110.4 ?
C1 C2 H2B . . 110.4 ?
C3 C2 H2B . . 110.4 ?
H2A C2 H2B . . 108.6 ?
N1 C3 C2 . . 102.70(14) ?
N1 C3 H3A . . 111.2 ?
C2 C3 H3A . . 111.2 ?
N1 C3 H3B . . 111.2 ?
C2 C3 H3B . . 111.2 ?
H3A C3 H3B . . 109.1 ?
N1 C4 C5 . . 107.75(16) ?
N1 C4 C1 . . 109.38(16) ?
C5 C4 C1 . . 142.83(17) ?
C4 C5 C6 . . 106.62(16) ?
C4 C5 H5 . . 126.7 ?
C6 C5 H5 . . 126.7 ?
C7 C6 C5 . . 108.24(17) ?
C7 C6 H6 . . 125.9 ?
C5 C6 H6 . . 125.9 ?
N1 C7 C6 . . 107.17(17) ?
N1 C7 H7 . . 126.4 ?
C6 C7 H7 . . 126.4 ?
O2 C8 C11 . . 127.76(18) ?
O2 C8 C9 . . 124.78(18) ?
C11 C8 C9 . . 107.47(15) ?
C8 C9 C10 . . 106.29(15) ?
C8 C9 H9A . . 110.5 ?
C10 C9 H9A . . 110.5 ?
C8 C9 H9B . . 110.5 ?
C10 C9 H9B . . 110.5 ?
H9A C9 H9B . . 108.7 ?
N2 C10 C9 . . 102.47(14) ?
N2 C10 H10A . . 111.3 ?
C9 C10 H10A . . 111.3 ?
N2 C10 H10B . . 111.3 ?
C9 C10 H10B . . 111.3 ?
H10A C10 H10B . . 109.2 ?
N2 C11 C12 . . 108.01(16) ?
N2 C11 C8 . . 108.92(16) ?
C12 C11 C8 . . 143.08(18) ?
C11 C12 C13 . . 106.13(17) ?
C11 C12 H12 . . 126.9 ?
C13 C12 H12 . . 126.9 ?
C14 C13 C12 . . 108.33(17) ?
C14 C13 H13 . . 125.8 ?
C12 C13 H13 . . 125.8 ?
N2 C14 C13 . . 107.47(17) ?
N2 C14 H14 . . 126.3 ?
C13 C14 H14 . . 126.3 ?
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 . 1.222(2) ?
O2 C8 . 1.232(2) ?
N1 C7 . 1.354(2) ?
N1 C4 . 1.374(2) ?
N1 C3 . 1.472(2) ?
N2 C14 . 1.343(2) ?
N2 C11 . 1.374(2) ?
N2 C10 . 1.469(2) ?
C1 C4 . 1.446(3) ?
C1 C2 . 1.530(3) ?
C2 C3 . 1.541(3) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.390(3) ?
C5 C6 . 1.404(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.393(2) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C11 . 1.438(3) ?
C8 C9 . 1.527(3) ?
C9 C10 . 1.541(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.393(3) ?
C12 C13 . 1.401(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.395(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 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 H6 O1 4_554 0.95 2.55 3.151(2) 121
C7 H7 O2 . 0.95 2.55 3.250(2) 130
C12 H12 O2 3_655 0.95 2.51 3.435(2) 165
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
O1 C1 C2 C3 . . . . 175.74(18) ?
C4 C1 C2 C3 . . . . -4.4(2) ?
C7 N1 C3 C2 . . . . -179.46(19) ?
C4 N1 C3 C2 . . . . -2.6(2) ?
C1 C2 C3 N1 . . . . 4.14(19) ?
C7 N1 C4 C5 . . . . -0.8(2) ?
C3 N1 C4 C5 . . . . -178.45(15) ?
C7 N1 C4 C1 . . . . 177.53(15) ?
C3 N1 C4 C1 . . . . -0.1(2) ?
O1 C1 C4 N1 . . . . -177.28(18) ?
C2 C1 C4 N1 . . . . 2.8(2) ?
O1 C1 C4 C5 . . . . 0.1(4) ?
C2 C1 C4 C5 . . . . -179.7(2) ?
N1 C4 C5 C6 . . . . 0.7(2) ?
C1 C4 C5 C6 . . . . -176.7(2) ?
C4 C5 C6 C7 . . . . -0.4(2) ?
C4 N1 C7 C6 . . . . 0.6(2) ?
C3 N1 C7 C6 . . . . 177.51(19) ?
C5 C6 C7 N1 . . . . -0.1(2) ?
O2 C8 C9 C10 . . . . -176.94(19) ?
C11 C8 C9 C10 . . . . 3.2(2) ?
C14 N2 C10 C9 . . . . -178.40(19) ?
C11 N2 C10 C9 . . . . 3.8(2) ?
C8 C9 C10 N2 . . . . -4.05(19) ?
C14 N2 C11 C12 . . . . 0.0(2) ?
C10 N2 C11 C12 . . . . 178.29(15) ?
C14 N2 C11 C8 . . . . 179.72(15) ?
C10 N2 C11 C8 . . . . -2.0(2) ?
O2 C8 C11 N2 . . . . 179.24(19) ?
C9 C8 C11 N2 . . . . -0.9(2) ?
O2 C8 C11 C12 . . . . -1.2(4) ?
C9 C8 C11 C12 . . . . 178.7(2) ?
N2 C11 C12 C13 . . . . 0.1(2) ?
C8 C11 C12 C13 . . . . -179.6(2) ?
C11 C12 C13 C14 . . . . -0.1(2) ?
C11 N2 C14 C13 . . . . 0.0(2) ?
C10 N2 C14 C13 . . . . -177.84(19) ?
C12 C13 C14 N2 . . . . 0.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079479
