#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/13/2001326.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_2001326
loop_
_publ_author_name
'Pohl, E.'
'Herbst-Irmer, R.'
'Noltemeyer, M.'
'Schneider, C.'
'Tietze, L. F.'
_publ_section_title
;Structures of endo- and
 exo-3-acetoxy-2,4-diethoxy-6-(2-oxo-1,3-oxazolidin-3-ylcarbonyl)-3,4-dihydro-2H-pyran
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1850
_journal_page_last               1852
_journal_paper_doi               10.1107/S0108270193004202
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C15 H21 N O8'
_chemical_formula_weight         343.33
_chemical_melting_point          116
_chemical_name_systematic
;
 exo 3-Acetoxy-2,4-diethoxy-6-(carbonyloxazolidin-2'-on)-3,4-dihydropyrane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                104.60(2)
_cell_angle_beta                 91.60(2)
_cell_angle_gamma                91.48(2)
_cell_formula_units_Z            2
_cell_length_a                   9.016(2)
_cell_length_b                   9.038(2)
_cell_length_c                   10.850(2)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     854.8(3)
_computing_cell_refinement       Stoe-DIF4
_computing_data_collection       Stoe-DIF4
_computing_data_reduction        Stoe-REDU4
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1990b)'
_computing_publication_material  'SHELXL-92 (Sheldrick, 1992)'
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1992)'
_computing_structure_solution    'SHELXS-90 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Stoe-Siemens AED2 four-circle'
_diffrn_measurement_method       'Profile data from 2θ/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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3293
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         3.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       Plates
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         .177
_refine_diff_density_min         -.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.058
_refine_ls_goodness_of_fit_obs   1.039
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_restrained_S_obs      1.039
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_obs          0.0401
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
; calc w = 1/[s^2^(F~o~^2^)+(0.0496P)^2^+0.3690P]
where P = (F~o~^2^+2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1124
_refine_ls_wR_factor_obs         0.1010
_reflns_number_observed          1931
_reflns_number_total             2220
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            na1040.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2001326
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.2055(2) 0.7505(2) 0.68972(14) 0.0501(4) Uani d . 1 . O
C2 0.2617(2) 0.8493(2) 0.6136(2) 0.0474(5) Uani d . 1 . C
H2 0.2103(2) 0.9461(2) 0.6353(2) 0.057 Uiso calc R 1 . H
C3 0.4263(2) 0.8814(2) 0.6367(2) 0.0483(5) Uani d . 1 . C
H3 0.4609(2) 0.9484(2) 0.5844(2) 0.058 Uiso calc R 1 . H
C4 0.4617(2) 0.9575(3) 0.7771(2) 0.0536(6) Uani d . 1 . C
H4 0.5673(2) 0.9473(3) 0.7961(2) 0.064 Uiso calc R 1 . H
C5 0.3705(2) 0.8831(3) 0.8588(2) 0.0542(6) Uani d . 1 . C
H5 0.3973(2) 0.9010(3) 0.9449(2) 0.065 Uiso calc R 1 . H
C6 0.2538(2) 0.7932(2) 0.8140(2) 0.0475(5) Uani d . 1 . C
C7 0.1587(3) 0.7241(2) 0.8965(2) 0.0513(6) Uani d . 1 . C
O7 0.2061(2) 0.6433(2) 0.9611(2) 0.0793(6) Uani d . 1 . O
O11 -0.1992(2) 0.8743(2) 0.8846(2) 0.0762(5) Uani d . 1 . O
C12 -0.0545(3) 0.8757(3) 0.8605(2) 0.0518(6) Uani d . 1 . C
O12 0.0040(2) 0.9716(2) 0.8188(2) 0.0698(5) Uani d . 1 . O
N13 0.0086(2) 0.7527(2) 0.8953(2) 0.0473(5) Uani d . 1 . N
C14 -0.0947(3) 0.6830(3) 0.9665(2) 0.0602(6) Uani d . 1 . C
H14A -0.0720(3) 0.7154(3) 1.0574(2) 0.072 Uiso calc R 1 . H
H14B -0.0952(3) 0.5723(3) 0.9388(2) 0.072 Uiso calc R 1 . H
C15 -0.2389(3) 0.7444(3) 0.9325(3) 0.0811(8) Uani d . 1 . C
H15A -0.2945(3) 0.6676(3) 0.8680(3) 0.097 Uiso calc R 1 . H
H15B -0.2988(3) 0.7751(3) 1.0070(3) 0.097 Uiso calc R 1 . H
O21 0.2290(2) 0.7756(2) 0.48796(14) 0.0536(4) Uani d . 1 . O
C22 0.0808(3) 0.7943(4) 0.4467(3) 0.0892(9) Uani d . 1 . C
H22A 0.0688(3) 0.9002(4) 0.4451(3) 0.107 Uiso calc R 1 . H
H22B 0.0125(3) 0.7711(4) 0.5073(3) 0.107 Uiso calc R 1 . H
C23 0.0438(4) 0.6970(5) 0.3220(3) 0.1018(11) Uani d . 1 . C
H23A -0.0540(12) 0.719(2) 0.2954(11) 0.153 Uiso calc R 1 . H
H23B 0.047(3) 0.5918(5) 0.3249(6) 0.153 Uiso calc R 1 . H
H23C 0.1143(18) 0.716(2) 0.2625(6) 0.153 Uiso calc R 1 . H
O31 0.5021(2) 0.7388(2) 0.6029(2) 0.0577(4) Uani d . 1 . O
C32 0.6369(3) 0.7428(3) 0.5531(2) 0.0607(6) Uani d . 1 . C
O33 0.6898(2) 0.8546(2) 0.5300(2) 0.0875(7) Uani d . 1 . O
C34 0.7080(3) 0.5925(3) 0.5339(3) 0.0880(10) Uani d . 1 . C
H34A 0.690(2) 0.5345(11) 0.4473(7) 0.132 Uiso calc R 1 . H
H34B 0.6667(18) 0.5375(11) 0.5905(15) 0.132 Uiso calc R 1 . H
H34C 0.8130(5) 0.6086(3) 0.551(2) 0.132 Uiso calc R 1 . H
O41 0.4281(2) 1.1152(2) 0.8063(2) 0.0636(5) Uani d . 1 . O
C42 0.5407(3) 1.2102(3) 0.7716(3) 0.0836(9) Uani d . 1 . C
H42A 0.5587(3) 1.1751(3) 0.6814(3) 0.100 Uiso calc R 1 . H
H42B 0.6326(3) 1.2059(3) 0.8190(3) 0.100 Uiso calc R 1 . H
C43 0.4884(5) 1.3693(4) 0.8016(4) 0.133(2) Uani d . 1 . C
H43A 0.5602(19) 1.4343(8) 0.775(3) 0.200 Uiso calc R 1 . H
H43B 0.476(4) 1.4050(14) 0.8917(5) 0.200 Uiso calc R 1 . H
H43C 0.3951(19) 1.3716(7) 0.757(3) 0.200 Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol. C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol. C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol. C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C6 O1 C2 . . 113.7(2) y
O21 C2 O1 . . 106.8(2) ?
O21 C2 C3 . . 111.0(2) ?
O1 C2 C3 . . 111.5(2) y
O31 C3 C2 . . 109.1(2) ?
O31 C3 C4 . . 108.4(2) ?
C2 C3 C4 . . 110.5(2) y
O41 C4 C5 . . 107.9(2) ?
O41 C4 C3 . . 110.7(2) ?
C5 C4 C3 . . 110.0(2) y
C6 C5 C4 . . 122.6(2) y
C5 C6 O1 . . 125.5(2) y
C5 C6 C7 . . 122.7(2) y
O1 C6 C7 . . 111.8(2) y
O7 C7 N13 . . 119.6(2) y
O7 C7 C6 . . 123.2(2) y
N13 C7 C6 . . 117.2(2) y
C12 O11 C15 . . 110.6(2) y
O12 C12 O11 . . 122.9(2) y
O12 C12 N13 . . 128.8(2) y
O11 C12 N13 . . 108.2(2) y
C7 N13 C12 . . 125.5(2) y
C7 N13 C14 . . 121.4(2) y
C12 N13 C14 . . 110.8(2) y
N13 C14 C15 . . 101.1(2) y
O11 C15 C14 . . 105.5(2) y
C2 O21 C22 . . 114.0(2) ?
O21 C22 C23 . . 112.3(3) ?
C32 O31 C3 . . 116.7(2) ?
O33 C32 O31 . . 123.0(2) ?
O33 C32 C34 . . 126.0(2) ?
O31 C32 C34 . . 111.0(2) ?
C4 O41 C42 . . 113.7(2) ?
O41 C42 C43 . . 108.0(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 C6 . 1.361(3) y
O1 C2 . 1.452(2) y
C2 O21 . 1.378(2) ?
C2 C3 . 1.506(3) y
C3 O31 . 1.443(3) ?
C3 C4 . 1.525(3) y
C4 O41 . 1.423(3) ?
C4 C5 . 1.492(3) y
C5 C6 . 1.316(3) y
C6 C7 . 1.492(3) y
C7 O7 . 1.210(3) y
C7 N13 . 1.384(3) y
O11 C12 . 1.338(3) y
O11 C15 . 1.440(3) y
C12 O12 . 1.192(3) y
C12 N13 . 1.391(3) y
N13 C14 . 1.455(3) y
C14 C15 . 1.499(4) y
O21 C22 . 1.425(3) ?
C22 C23 . 1.441(4) ?
O31 C32 . 1.348(3) ?
C32 O33 . 1.192(3) ?
C32 C34 . 1.486(4) ?
O41 C42 . 1.431(3) ?
C42 C43 . 1.485(5) ?
