#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/24/2212499.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_2212499
loop_
_publ_author_name
'Švorc, Ľubomír'
'Vrábel, Viktor'
'Kožíšek, Jozef'
'Marchalín, Štefan'
'Žúžiová, Jozefína'
_publ_section_title
(3aR,4R,4aS,9aR)-4-Hydroxyperhydrofuro[2,3-f]indolizin-7(2H)-one
_journal_coeditor_code           BV2048
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1452
_journal_page_last               o1454
_journal_paper_doi               10.1107/S1600536807008537
_journal_volume                  63
_journal_year                    2007
_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
;
(3aR,4R,4aS,9aR)-4-Hydroxyperhydrofuro[2,3-f]indolizin-7(2H)-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3423(2)
_cell_length_b                   8.6807(2)
_cell_length_c                   13.7985(3)
_cell_measurement_reflns_used    8947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9109
_cell_measurement_theta_min      3.3711
_cell_volume                     999.25(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2002)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2002)
;
_computing_data_reduction
;
CrysAlis RED
;
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4340
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method
'Rotation method data acquisition using ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23008
_diffrn_reflns_theta_full        29.04
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         3.39
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.177
_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     132
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0392
_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)+(0.0546P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                935
_reflns_number_total             1491
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2048.cif
_cod_data_source_block           I
_cod_database_code               2212499
_cod_database_fobs_code          2212499
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
N N8 -0.07367(18) -0.06371(17) -0.77831(9) 0.0436(4) Uani d . 1
C C10 0.2044(2) -0.0465(2) -0.83184(14) 0.0501(5) Uani d . 1
H H10 0.3080 -0.0965 -0.8204 0.060 Uiso calc R 1
C C4 -0.0277(2) -0.0551(2) -0.95070(12) 0.0440(4) Uani d . 1
H H4 -0.0449 0.0565 -0.9539 0.053 Uiso calc R 1
C C7 -0.1879(2) -0.0192(2) -0.71723(13) 0.0467(5) Uani d . 1
C C11 0.1484(2) -0.0853(2) -0.93397(13) 0.0459(5) Uani d . 1
H H11 0.1737 -0.1929 -0.9491 0.055 Uiso calc R 1
C C12 -0.1320(2) -0.1208(2) -0.87143(12) 0.0466(5) Uani d . 1
H H12 -0.1264 -0.2335 -0.8726 0.056 Uiso calc R 1
C C9 0.0916(2) -0.0901(2) -0.75169(12) 0.0504(5) Uani d . 1
H H9A 0.1062 -0.1981 -0.7360 0.060 Uiso calc R 1
H H9B 0.1169 -0.0303 -0.6943 0.060 Uiso calc R 1
C C6 -0.3465(3) -0.0331(3) -0.76714(14) 0.0634(6) Uani d . 1
H H6A -0.4061 0.0625 -0.7623 0.076 Uiso calc R 1
H H6B -0.4097 -0.1152 -0.7386 0.076 Uiso calc R 1
C C5 -0.3072(2) -0.0691(3) -0.87200(14) 0.0660(6) Uani d . 1
H H5A -0.3209 0.0215 -0.9123 0.079 Uiso calc R 1
H H5B -0.3759 -0.1505 -0.8964 0.079 Uiso calc R 1
C C3 0.2539(3) 0.0215(3) -0.99330(15) 0.0676(6) Uani d . 1
H H3A 0.3567 -0.0258 -1.0073 0.081 Uiso calc R 1
H H3B 0.2024 0.0496 -1.0538 0.081 Uiso calc R 1
C C2 0.2731(3) 0.1598(3) -0.92791(17) 0.0839(8) Uani d . 1
H H2A 0.3837 0.1943 -0.9282 0.101 Uiso calc R 1
H H2B 0.2060 0.2437 -0.9506 0.101 Uiso calc R 1
O O3 -0.16378(18) 0.02292(17) -0.63290(9) 0.0625(4) Uani d . 1
O O2 -0.06689(19) -0.12052(18) -1.04207(9) 0.0644(4) Uani d . 1
H H2 -0.167(3) -0.079(3) -1.0655(19) 0.101(9) Uiso d . 1
O O1 0.22707(18) 0.11594(17) -0.83249(11) 0.0709(5) Uani d . 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 0.0000 '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
C7 N8 C9 124.7(2) yes
C7 N8 C12 114.7(2) yes
C9 N8 C12 119.2(2) yes
O1 C10 C9 109.8(2) yes
O1 C10 C11 104.73(17) ?
C9 C10 C11 115.73(16) ?
O1 C10 H10 108.8 ?
C9 C10 H10 108.8 ?
C11 C10 H10 108.8 ?
O2 C4 C12 111.1(2) yes
O2 C4 C11 106.86(16) ?
C12 C4 C11 112.60(15) ?
O2 C4 H4 108.7 ?
C12 C4 H4 108.7 ?
C11 C4 H4 108.7 ?
O3 C7 N8 124.5(3) yes
O3 C7 C6 126.94(18) ?
N8 C7 C6 108.57(15) ?
C4 C11 C3 112.03(16) ?
C4 C11 C10 113.7(2) yes
C3 C11 C10 100.74(16) ?
C4 C11 H11 110.0 ?
C3 C11 H11 110.0 ?
C10 C11 H11 110.0 ?
N8 C12 C4 108.5(2) yes
N8 C12 C5 102.91(15) ?
C4 C12 C5 115.9(2) ?
N8 C12 H12 109.8 ?
C4 C12 H12 109.8 ?
C5 C12 H12 109.8 ?
N8 C9 C10 111.76(14) ?
N8 C9 H9A 109.3 ?
C10 C9 H9A 109.3 ?
N8 C9 H9B 109.3 ?
C10 C9 H9B 109.3 ?
H9A C9 H9B 107.9 ?
C7 C6 C5 105.35(17) ?
C7 C6 H6A 110.7 ?
C5 C6 H6A 110.7 ?
C7 C6 H6B 110.7 ?
C5 C6 H6B 110.7 ?
H6A C6 H6B 108.8 ?
C6 C5 C12 105.21(16) ?
C6 C5 H5A 110.7 ?
C12 C5 H5A 110.7 ?
C6 C5 H5B 110.7 ?
C12 C5 H5B 110.7 ?
H5A C5 H5B 108.8 ?
C2 C3 C11 103.00(16) ?
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 ?
O1 C2 C3 108.13(18) ?
O1 C2 H2A 110.1 ?
C3 C2 H2A 110.1 ?
O1 C2 H2B 110.1 ?
C3 C2 H2B 110.1 ?
H2A C2 H2B 108.4 ?
C4 O2 H2 110.4(16) ?
C10 O1 C2 107.9(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N8 C7 1.330(2) yes
N8 C9 1.445(2) yes
N8 C12 1.460(2) yes
C10 O1 1.423(3) yes
C10 C9 1.500(3) ?
C10 C11 1.522(3) ?
C10 H10 0.9800 ?
C4 O2 1.421(2) ?
C4 C12 1.510(3) yes
C4 C11 1.510(3) ?
C4 H4 0.9800 ?
C7 O3 1.236(2) yes
C7 C6 1.496(3) ?
C11 C3 1.518(3) yes
C11 H11 0.9800 ?
C12 C5 1.529(3) ?
C12 H12 0.9800 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C6 C5 1.516(3) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C3 C2 1.511(3) yes
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C2 O1 1.423(3) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
O2 H2 0.97(3) ?
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
O2 H2 O3 2_454 0.97(3) 1.76(3) 2.709(2) 167(2)
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
C9 N8 C7 O3 9.1(3) ?
C12 N8 C7 O3 175.07(17) ?
C9 N8 C7 C6 -169.49(18) ?
C12 N8 C7 C6 -3.5(2) ?
O2 C4 C11 C3 76.3(2) yes
C12 C4 C11 C3 -161.49(15) ?
O2 C4 C11 C10 -170.30(15) ?
C12 C4 C11 C10 -48.1(2) ?
O1 C10 C11 C4 -80.50(19) ?
C9 C10 C11 C4 40.5(2) ?
O1 C10 C11 C3 39.50(18) ?
C9 C10 C11 C3 160.47(17) ?
C7 N8 C12 C4 136.99(17) ?
C9 N8 C12 C4 -56.2(2) ?
C7 N8 C12 C5 13.7(2) ?
C9 N8 C12 C5 -179.50(17) ?
O2 C4 C12 N8 173.23(15) ?
C11 C4 C12 N8 53.4(2) ?
O2 C4 C12 C5 -71.7(2) yes
C11 C4 C12 C5 168.55(17) ?
C7 N8 C9 C10 -145.88(18) ?
C12 N8 C9 C10 48.7(2) ?
O1 C10 C9 N8 79.6(2) ?
C11 C10 C9 N8 -38.6(2) yes
O3 C7 C6 C5 173.0(2) ?
N8 C7 C6 C5 -8.5(2) yes
C7 C6 C5 C12 16.2(3) ?
N8 C12 C5 C6 -17.7(2) ?
C4 C12 C5 C6 -135.9(2) ?
C4 C11 C3 C2 88.2(2) ?
C10 C11 C3 C2 -32.9(2) ?
C11 C3 C2 O1 16.3(3) yes
C9 C10 O1 C2 -155.4(2) yes
C11 C10 O1 C2 -30.6(2) ?
C3 C2 O1 C10 8.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21185515
