#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/23/4022308.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_4022308
loop_
_publ_author_name
'Ramon Alibés'
'Pedro de March'
'Marta Figueredo'
'Josep Font'
'Xiaolin Fu'
'Marta Racamonde'
'Ángel Álvarez-Larena'
'Juan F. Piniella'
_publ_section_title
;
 Photochemical [2 + 2] Cycloaddition of Acetylene
 to Chiral 2(5H)-Furanones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1283
_journal_page_last               1289
_journal_paper_doi               10.1021/jo0264731
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C13 H18 O4'
_chemical_formula_weight         238.27
_chemical_name_systematic
;
(1R,4S,5S)-5-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]
hept-6-en-2-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                   9.999(3)
_cell_length_b                   10.016(8)
_cell_length_c                   13.119(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.89
_cell_measurement_theta_min      11.64
_cell_volume                     1313.9(12)
_computing_cell_refinement       'CAD4 (Enraf-Nonius)'
_computing_data_collection       'CAD4 (Enraf-Nonius)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'omega/2theta scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1340
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5.3(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0697P)²+0.0136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                1126
_reflns_number_total             1340
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0264731si20021209_062153_2.cif
_cod_data_source_block           compound3e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.0136P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.0136P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4022308
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.04429(17) -0.59405(18) -0.50812(11) 0.0712(5) Uani 1 d .
C2 C -0.1607(3) -0.6181(3) -0.46136(17) 0.0690(7) Uani 1 d .
C3 C -0.2390(2) -0.7193(2) -0.51875(18) 0.0640(6) Uani 1 d .
H3 H -0.3352 -0.7032 -0.5260 0.077 Uiso 1 calc R
C4 C -0.1959(3) -0.8602(3) -0.4892(2) 0.0830(8) Uani 1 d .
H4 H -0.2157 -0.9152 -0.4341 0.100 Uiso 1 calc R
C5 C -0.1198(3) -0.8751(2) -0.5711(2) 0.0742(7) Uani 1 d .
H5 H -0.0628 -0.9431 -0.5922 0.089 Uiso 1 calc R
C6 C -0.1582(2) -0.7428(2) -0.61836(16) 0.0564(5) Uani 1 d .
C7 C -0.0487(2) -0.6371(2) -0.61238(16) 0.0603(6) Uani 1 d .
H7 H 0.0371 -0.6784 -0.6299 0.072 Uiso 1 calc R
O8 O -0.1880(3) -0.5653(2) -0.38184(14) 0.1141(8) Uani 1 d .
C9 C -0.2335(3) -0.7523(3) -0.7178(2) 0.0886(9) Uani 1 d .
H9A H -0.2542 -0.6642 -0.7418 0.133 Uiso 1 calc R
H9B H -0.3149 -0.8013 -0.7075 0.133 Uiso 1 calc R
H9C H -0.1792 -0.7975 -0.7674 0.133 Uiso 1 calc R
C10 C -0.0678(2) -0.5149(3) -0.67702(19) 0.0699(7) Uani 1 d .
H10A H 0.0040 -0.4516 -0.6651 0.084 Uiso 1 calc R
H10B H -0.0682 -0.5387 -0.7487 0.084 Uiso 1 calc R
O11 O -0.19400(14) -0.45788(15) -0.64839(12) 0.0611(4) Uani 1 d .
C12 C -0.2127(2) -0.3281(2) -0.66468(16) 0.0598(6) Uani 1 d .
O13 O -0.1292(2) -0.2599(2) -0.7034(2) 0.1039(7) Uani 1 d .
C14 C -0.3460(2) -0.2796(2) -0.62550(17) 0.0610(6) Uani 1 d .
C15 C -0.4526(3) -0.3872(3) -0.6345(2) 0.0811(7) Uani 1 d .
H15A H -0.5363 -0.3531 -0.6099 0.122 Uiso 1 calc R
H15B H -0.4268 -0.4634 -0.5946 0.122 Uiso 1 calc R
H15C H -0.4619 -0.4130 -0.7046 0.122 Uiso 1 calc R
C16 C -0.3877(4) -0.1564(3) -0.6857(3) 0.0978(10) Uani 1 d .
H16A H -0.4726 -0.1252 -0.6613 0.147 Uiso 1 calc R
H16B H -0.3948 -0.1789 -0.7566 0.147 Uiso 1 calc R
H16C H -0.3218 -0.0876 -0.6770 0.147 Uiso 1 calc R
C17 C -0.3248(4) -0.2429(4) -0.5137(2) 0.1081(11) Uani 1 d .
H17A H -0.4072 -0.2104 -0.4855 0.162 Uiso 1 calc R
H17B H -0.2576 -0.1747 -0.5088 0.162 Uiso 1 calc R
H17C H -0.2963 -0.3204 -0.4766 0.162 Uiso 1 calc R
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'
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
C2 O1 C7 110.87(19)
O8 C2 O1 121.2(3)
O8 C2 C3 128.3(3)
O1 C2 C3 110.43(19)
C2 C3 C4 110.7(2)
C2 C3 C6 104.80(19)
C4 C3 C6 85.80(19)
C5 C4 C3 93.4(2)
C4 C5 C6 95.0(2)
C9 C6 C5 115.2(2)
C9 C6 C7 116.5(2)
C5 C6 C7 113.89(19)
C9 C6 C3 118.50(19)
C5 C6 C3 85.44(18)
C7 C6 C3 102.98(18)
O1 C7 C10 107.3(2)
O1 C7 C6 106.26(17)
C10 C7 C6 116.5(2)
O11 C10 C7 106.78(17)
C12 O11 C10 118.08(18)
O13 C12 O11 121.9(2)
O13 C12 C14 125.4(2)
O11 C12 C14 112.58(19)
C12 C14 C15 111.39(19)
C12 C14 C16 109.0(2)
C15 C14 C16 110.0(2)
C12 C14 C17 106.4(2)
C15 C14 C17 110.0(2)
C16 C14 C17 109.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.337(3)
O1 C7 1.435(3)
C2 O8 1.201(3)
C2 C3 1.486(4)
C3 C4 1.526(4)
C3 C6 1.554(3)
C4 C5 1.326(4)
C5 C6 1.512(3)
C6 C9 1.509(3)
C6 C7 1.525(3)
C7 C10 1.501(3)
C10 O11 1.435(3)
O11 C12 1.331(3)
C12 O13 1.192(3)
C12 C14 1.509(3)
C14 C15 1.520(4)
C14 C16 1.523(4)
C14 C17 1.527(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9196125
