#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/47/2204784.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_2204784
loop_
_publ_author_name
'Vrábel, Viktor'
'Kožíšek, Jozef'
'Langer, Vratislav'
'Marchalín, Štefan'
'Szemes, Fridrich'
_publ_section_title
(3aS,8aS,9R,9aS)-9-Hydroxy-2,3,3a,7,8,8a,9,9a-octahydrofuro[3,2-f]indolizin-6(4H)-one
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2211
_journal_page_last               o2213
_journal_paper_doi               10.1107/S1600536804027515
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C10 H15 N O3'
_chemical_formula_moiety         'C10 H15 N O3'
_chemical_formula_sum            'C10 H15 N O3'
_chemical_formula_weight         197.23
_chemical_name_systematic
;
(3aS,8aS,9R,9aS)-9-Hydroxy-2,3,3a,7,8,8a,9,9a-octahydrofuro[3,2-f]indolizin-
6(4H)-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.1270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3003(3)
_cell_length_b                   10.3540(5)
_cell_length_c                   8.5137(4)
_cell_measurement_reflns_used    3686
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      33.00
_cell_measurement_theta_min      2.41
_cell_volume                     464.56(4)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT and SADABS (Sheldrick, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Bruker, 2001)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0851
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7003
_diffrn_reflns_theta_full        33.00
_diffrn_reflns_theta_max         33.00
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.9645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0674
_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)+(0.088P)²+0.2047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1664
_reflns_number_gt                1377
_reflns_number_total             1748
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            rz6013.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2204784
_cod_database_fobs_code          2204784
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_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_type_symbol
O1 0.2012(5) 0.0583(2) 0.4452(3) 0.0317(6) Uani d . 1 O
C2 0.4231(7) 0.1246(4) 0.5192(4) 0.0288(7) Uani d . 1 C
H2A 0.5793 0.0837 0.4883 0.035 Uiso calc R 1 H
H2B 0.4273 0.1206 0.6356 0.035 Uiso calc R 1 H
C3 0.4068(7) 0.2650(3) 0.4634(4) 0.0237(6) Uani d . 1 C
H3A 0.5193 0.2808 0.3798 0.028 Uiso calc R 1 H
H3B 0.4524 0.3253 0.5521 0.028 Uiso calc R 1 H
C4 0.0601(6) 0.3882(3) 0.2801(4) 0.0196(6) Uani d . 1 C
H4A -0.1219 0.4103 0.2783 0.024 Uiso calc R 1 H
H4B 0.1605 0.4660 0.3134 0.024 Uiso calc R 1 H
N5 0.1140(5) 0.3497(2) 0.1211(3) 0.0178(5) Uani d . 1 N
C6 0.2926(6) 0.4018(3) 0.0411(3) 0.0180(6) Uani d . 1 C
C7 0.3042(6) 0.3250(3) -0.1108(4) 0.0230(6) Uani d . 1 C
H7A 0.4697 0.2807 -0.1105 0.028 Uiso calc R 1 H
H7B 0.2788 0.3823 -0.2043 0.028 Uiso calc R 1 H
C8 0.0876(7) 0.2267(3) -0.1118(4) 0.0257(7) Uani d . 1 C
H8A 0.1448 0.1399 -0.1414 0.031 Uiso calc R 1 H
H8B -0.0585 0.2529 -0.1873 0.031 Uiso calc R 1 H
C9 0.1393(6) 0.1203(3) 0.1656(4) 0.0218(6) Uani d . 1 C
H9 0.0732 0.0345 0.1263 0.026 Uiso calc R 1 H
C10 0.0657(6) 0.1427(3) 0.3336(4) 0.0222(6) Uani d . 1 C
H10 -0.1202 0.1263 0.3337 0.027 Uiso calc R 1 H
C11 0.1259(6) 0.2791(3) 0.3987(4) 0.0206(6) Uani d . 1 C
H11 0.0261 0.2930 0.4905 0.025 Uiso calc R 1 H
C12 0.0152(6) 0.2271(3) 0.0592(4) 0.0197(6) Uani d . 1 C
H12 -0.1735 0.2244 0.0589 0.024 Uiso calc R 1 H
O13 0.4067(4) 0.1229(2) 0.1648(3) 0.0228(5) Uani d . 1 O
H13 0.432(8) 0.100(5) 0.072(5) 0.023(10) Uiso d . 1 H
O14 0.4247(5) 0.4971(2) 0.0825(3) 0.0267(5) Uani d . 1 O
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C10 O1 C2 109.1(2) y
O1 C2 C3 107.4(3) ?
O1 C2 H2A 110.2 ?
C3 C2 H2A 110.2 ?
O1 C2 H2B 110.2 ?
C3 C2 H2B 110.2 ?
H2A C2 H2B 108.5 ?
C2 C3 C11 102.8(3) ?
C2 C3 H3A 111.2 ?
C11 C3 H3A 111.2 ?
C2 C3 H3B 111.2 ?
C11 C3 H3B 111.2 ?
H3A C3 H3B 109.1 ?
N5 C4 C11 110.8(2) ?
N5 C4 H4A 109.5 ?
C11 C4 H4A 109.5 ?
N5 C4 H4B 109.5 ?
C11 C4 H4B 109.5 ?
H4A C4 H4B 108.1 ?
C6 N5 C12 114.5(3) ?
C6 N5 C4 125.3(3) y
C12 N5 C4 118.3(3) y
O14 C6 N5 125.8(3) y
O14 C6 C7 125.7(3) ?
N5 C6 C7 108.4(3) ?
C6 C7 C8 104.7(3) ?
C6 C7 H7A 110.8 ?
C8 C7 H7A 110.8 ?
C6 C7 H7B 110.8 ?
C8 C7 H7B 110.8 ?
H7A C7 H7B 108.9 ?
C7 C8 C12 104.7(3) ?
C7 C8 H8A 110.8 ?
C12 C8 H8A 110.8 ?
C7 C8 H8B 110.8 ?
C12 C8 H8B 110.8 ?
H8A C8 H8B 108.9 ?
O13 C9 C12 110.5(2) y
O13 C9 C10 110.7(3) ?
C12 C9 C10 107.8(2) ?
O13 C9 H9 109.3 ?
C12 C9 H9 109.3 ?
C10 C9 H9 109.3 ?
O1 C10 C11 104.6(3) ?
O1 C10 C9 111.5(3) ?
C11 C10 C9 114.2(3) y
O1 C10 H10 108.8 ?
C11 C10 H10 108.8 ?
C9 C10 H10 108.8 ?
C4 C11 C10 114.6(3) ?
C4 C11 C3 116.7(3) ?
C10 C11 C3 101.4(3) ?
C4 C11 H11 107.9 ?
C10 C11 H11 107.9 ?
C3 C11 H11 107.9 ?
N5 C12 C9 107.5(2) y
N5 C12 C8 103.2(2) ?
C9 C12 C8 114.9(3) y
N5 C12 H12 110.3 ?
C9 C12 H12 110.3 ?
C8 C12 H12 110.3 ?
C9 O13 H13 105(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.427(4) y
O1 C2 1.446(5) ?
C2 C3 1.529(5) ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C11 1.538(5) y
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 N5 1.468(4) ?
C4 C11 1.531(4) ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
N5 C6 1.338(4) y
N5 C12 1.451(4) y
C6 O14 1.239(4) y
C6 C7 1.524(4) ?
C7 C8 1.533(5) ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 C12 1.545(5) y
C8 H8A 0.9900 ?
C8 H8B 0.9900 ?
C9 O13 1.418(4) y
C9 C12 1.533(4) y
C9 C10 1.540(5) ?
C9 H9 1.0000 ?
C10 C11 1.538(4) ?
C10 H10 1.0000 ?
C11 H11 1.0000 ?
C12 H12 1.0000 ?
O13 H13 0.85(5) ?
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
O13 H13 O14 2_645 0.85(5) 1.92(5) 2.708(3) 155(4) y
C3 H3A O13 . 0.99 2.48 2.937(4) 108 y
C4 H4B O14 . 0.99 2.55 2.920(4) 102 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
C10 O1 C2 C3 7.0(4) ?
O1 C2 C3 C11 17.3(3) y
C11 C4 N5 C6 -113.5(3) ?
C11 C4 N5 C12 50.2(4) ?
C12 N5 C6 O14 -170.8(3) ?
C4 N5 C6 O14 -6.6(5) ?
C12 N5 C6 C7 9.9(3) ?
C4 N5 C6 C7 174.1(3) ?
O14 C6 C7 C8 -174.9(3) ?
N5 C6 C7 C8 4.5(3) y
C6 C7 C8 C12 -15.5(3) ?
C2 O1 C10 C11 -28.6(3) ?
C2 O1 C10 C9 95.2(3) y
O13 C9 C10 O1 -51.0(3) y
C12 C9 C10 O1 -172.0(3) ?
O13 C9 C10 C11 67.3(3) ?
C12 C9 C10 C11 -53.7(3) ?
N5 C4 C11 C10 -37.3(4) y
N5 C4 C11 C3 80.9(3) ?
O1 C10 C11 C4 164.9(3) ?
C9 C10 C11 C4 42.7(4) ?
O1 C10 C11 C3 38.2(3) ?
C9 C10 C11 C3 -83.9(3) ?
C2 C3 C11 C4 -158.1(3) ?
C2 C3 C11 C10 -32.9(3) ?
C6 N5 C12 C9 102.2(3) ?
C4 N5 C12 C9 -63.2(3) ?
C6 N5 C12 C8 -19.6(3) ?
C4 N5 C12 C8 175.0(3) ?
O13 C9 C12 N5 -60.3(3) ?
C10 C9 C12 N5 60.8(3) ?
O13 C9 C12 C8 53.9(3) y
C10 C9 C12 C8 175.0(3) ?
C7 C8 C12 N5 20.5(3) ?
C7 C8 C12 C9 -96.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173797
