#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/24/2212489.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_2212489
loop_
_publ_author_name
'Christian Peifer'
'Melanie Tschertsche'
'Schollmeyer, Dieter'
'Stefan Laufer'
_publ_section_title
(1aR,2aS,5aS,5bS)-Perhydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one
_journal_coeditor_code           BT2270
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1359
_journal_page_last               o1360
_journal_paper_doi               10.1107/S160053680700743X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H8 O3'
_chemical_formula_moiety         'C7 H8 O3'
_chemical_formula_sum            'C7 H8 O3'
_chemical_formula_weight         140.137
_chemical_melting_point          75.3
_chemical_name_common
;
(1aR,2aS,5aS,5bS)-Perhydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8759(5)
_cell_length_b                   9.5110(8)
_cell_length_c                   14.1724(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      36
_cell_measurement_theta_min      26
_cell_volume                     657.24(10)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CORINC (Dräger & Gattow, 1971)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1508
_diffrn_reflns_theta_full        70.06
_diffrn_reflns_theta_max         70.06
_diffrn_reflns_theta_min         5.60
_diffrn_standards_decay_%        10
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0418
_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)+(0.0652P)²+0.0616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1086
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                593
_reflns_number_total             754
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2270.cif
_cod_data_source_block           VI
_cod_database_code               2212489
_cod_database_fobs_code          2212489
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
O O1 0.3693(4) -0.0810(3) 0.55389(16) 0.0664(7) Uani d . 1
C C1A 0.1292(7) -0.0761(4) 0.4944(2) 0.0681(9) Uani d . 1
H H1A 0.1201 -0.1337 0.4371 0.077(11) Uiso calc R 1
C C2 -0.0097(8) 0.0628(4) 0.4977(3) 0.0759(10) Uani d . 1
H H21 -0.1815 0.0600 0.4632 0.091(9) Uiso calc R 1
H H22 0.1061 0.1352 0.4705 0.091(9) Uiso calc R 1
C C2A -0.0597(7) 0.0907(4) 0.6012(2) 0.0643(9) Uani d . 1
H H2A -0.2414 0.1322 0.6111 0.074(11) Uiso calc R 1
O O3 0.1541(6) 0.1796(2) 0.64129(18) 0.0733(7) Uani d . 1
C C4 0.2665(8) 0.1218(4) 0.7182(3) 0.0649(9) Uani d . 1
C C5 0.1274(7) -0.0133(4) 0.7415(2) 0.0632(9) Uani d . 1
H H51 0.0060 -0.0020 0.7952 0.108(11) Uiso calc R 1
H H52 0.2608 -0.0859 0.7559 0.108(11) Uiso calc R 1
C C5A -0.0333(6) -0.0502(3) 0.65367(19) 0.0521(7) Uani d . 1
H H5A -0.2136 -0.0893 0.6694 0.078(11) Uiso calc R 1
C C5B 0.1166(7) -0.1416(3) 0.5859(2) 0.0604(9) Uani d . 1
H H5B 0.0993 -0.2440 0.5906 0.083(11) Uiso calc R 1
O O6 0.4511(7) 0.1785(3) 0.7596(2) 0.0966(10) Uani d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0437(11) 0.0740(15) 0.0814(15) 0.0033(12) -0.0006(12) -0.0160(13)
C1A 0.0580(18) 0.085(2) 0.0615(19) -0.007(2) -0.0077(18) -0.0113(19)
C2 0.067(2) 0.088(2) 0.073(2) 0.000(2) -0.007(2) 0.025(2)
C2A 0.0460(16) 0.0570(17) 0.090(2) 0.0086(16) 0.0085(17) 0.0097(17)
O3 0.0845(16) 0.0443(10) 0.0913(17) -0.0052(13) 0.0232(17) 0.0011(12)
C4 0.066(2) 0.0584(18) 0.071(2) -0.0114(18) 0.0243(19) -0.0215(17)
C5 0.063(2) 0.068(2) 0.0579(17) -0.0123(18) 0.0102(19) -0.0003(15)
C5A 0.0420(15) 0.0505(16) 0.0639(18) -0.0065(14) 0.0015(15) 0.0069(14)
C5B 0.057(2) 0.0475(16) 0.077(2) -0.0065(15) -0.0075(18) -0.0068(15)
O6 0.092(2) 0.103(2) 0.0948(19) -0.0387(19) 0.0165(17) -0.0450(15)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
C5B O1 C1A 60.1(2)
C5B C1A O1 59.6(2)
C5B C1A C2 109.7(3)
O1 C1A C2 112.3(3)
C5B C1A H1A 120.2
O1 C1A H1A 120.2
C2 C1A H1A 120.2
C1A C2 C2A 105.1(3)
C1A C2 H21 110.7
C2A C2 H21 110.7
C1A C2 H22 110.7
C2A C2 H22 110.7
H21 C2 H22 108.8
O3 C2A C2 111.4(3)
O3 C2A C5A 104.9(3)
C2 C2A C5A 107.6(3)
O3 C2A H2A 110.9
C2 C2A H2A 110.9
C5A C2A H2A 110.9
C4 O3 C2A 111.9(3)
O6 C4 O3 121.3(4)
O6 C4 C5 128.2(4)
O3 C4 C5 110.4(3)
C4 C5 C5A 104.6(3)
C4 C5 H51 110.8
C5A C5 H51 110.8
C4 C5 H52 110.8
C5A C5 H52 110.8
H51 C5 H52 108.9
C5B C5A C5 114.4(3)
C5B C5A C2A 103.7(3)
C5 C5A C2A 103.9(2)
C5B C5A H5A 111.5
C5 C5A H5A 111.5
C2A C5A H5A 111.5
O1 C5B C1A 60.3(2)
O1 C5B C5A 113.1(2)
C1A C5B C5A 110.5(3)
O1 C5B H5B 119.6
C1A C5B H5B 119.6
C5A C5B H5B 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5B 1.434(4)
O1 C1A 1.444(4)
C1A C5B 1.440(5)
C1A C2 1.485(5)
C1A H1A 0.9800
C2 C2A 1.511(5)
C2 H21 0.9700
C2 H22 0.9700
C2A O3 1.458(4)
C2A C5A 1.538(4)
C2A H2A 0.9800
O3 C4 1.338(4)
C4 O6 1.202(4)
C4 C5 1.490(5)
C5 C5A 1.513(4)
C5 H51 0.9700
C5 H52 0.9700
C5A C5B 1.487(4)
C5A H5A 0.9800
C5B H5B 0.9800
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
C5B O1 C1A C2 100.4(3)
C5B C1A C2 C2A 10.7(4)
O1 C1A C2 C2A -53.6(4)
C1A C2 C2A O3 96.8(3)
C1A C2 C2A C5A -17.6(4)
C2 C2A O3 C4 -126.7(3)
C5A C2A O3 C4 -10.6(3)
C2A O3 C4 O6 178.2(3)
C2A O3 C4 C5 -2.7(4)
O6 C4 C5 C5A -166.0(3)
O3 C4 C5 C5A 15.0(3)
C4 C5 C5A C5B 92.1(3)
C4 C5 C5A C2A -20.2(3)
O3 C2A C5A C5B -100.9(3)
C2 C2A C5A C5B 17.8(4)
O3 C2A C5A C5 18.9(3)
C2 C2A C5A C5 137.7(3)
C1A O1 C5B C5A -101.3(3)
C2 C1A C5B O1 -104.9(3)
O1 C1A C5B C5A 105.6(3)
C2 C1A C5B C5A 0.6(4)
C5 C5A C5B O1 -58.4(3)
C2A C5A C5B O1 54.1(3)
C5 C5A C5B C1A -123.8(3)
C2A C5A C5B C1A -11.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21185518
