Stereoselective rearrangement of guaianolides to tricyclic δ-valerolactones.
Schanderl, Martin; Jeong, Won Boo; Schwarz, Michael; Reiser, Oliver; Organic & biomolecular chemistry 9 (2011) 2543–2547; doi:10.1039/c0ob00919a

data_7151776
_publ_section_title
;
 Stereoselective rearrangement of guaianolides to tricyclic
 \d-valerolactones.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2543
_journal_page_last               2547
_journal_paper_doi               10.1039/c0ob00919a
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C16 H22 O4'
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.34
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.1609(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9518(3)
_cell_length_b                   8.62335(15)
_cell_length_c                   9.25071(15)
_cell_measurement_reflns_used    4295
_cell_measurement_temperature    123
_cell_measurement_theta_max      76.0817
_cell_measurement_theta_min      4.8042
_cell_volume                     1423.78(4)
_computing_cell_refinement
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
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_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
;
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.3546
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
1 omega -117.00 -45.00 1.2000 2.0000
omega____ theta____ kappa____ phi______ frames
- -41.0814 -169.0000 -44.0000 60

2 omega -117.00 -21.00 1.2000 2.0000
omega____ theta____ kappa____ phi______ frames
- -41.0814 -38.0000 0.0000 80

3 omega -46.00 -6.40 1.2000 2.0000
omega____ theta____ kappa____ phi______ frames
- -41.0814 125.0000 -180.0000 33

4 omega -123.00 -47.40 1.2000 2.0000
omega____ theta____ kappa____ phi______ frames
- -41.0814 -169.0000 27.0000 63

5 omega 13.00 109.00 1.2000 2.0000
omega____ theta____ kappa____ phi______ frames
- 41.0814 77.0000 90.0000 80

6 omega -78.00 -51.60 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 90.0000 22

7 omega -76.00 -49.60 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 60.0000 22

8 omega -76.00 -49.60 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -77.0000 30.0000 22

9 omega -103.80 -51.00 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- -83.0000 -71.0000 -5.0000 44

10 omega 37.00 109.00 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -115.0000 99.0000 60

11 omega 46.00 76.00 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -120.0000 25

12 omega 38.00 72.80 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -60.0000 29

13 omega 79.00 154.60 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 60.0000 63

14 omega 41.00 69.80 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -90.0000 24

15 omega 86.00 156.80 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 45.0000 0.0000 59

16 omega 81.00 129.00 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 30.0000 40

17 omega 54.00 157.20 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 15.0000 -150.0000 86

18 omega 79.00 141.40 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 90.0000 52

19 omega 89.00 155.00 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 77.0000 -150.0000 55

20 omega 40.00 60.40 1.2000 8.0000
omega____ theta____ kappa____ phi______ frames
- 113.0000 -45.0000 -30.0000 17

;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0104
_diffrn_reflns_av_sigmaI/netI    0.0107
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4531
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        76.27
_diffrn_reflns_theta_max         76.27
_diffrn_reflns_theta_min         4.81
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       'flat parallelepiped'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.3052
_exptl_crystal_size_mid          0.1169
_exptl_crystal_size_min          0.0594
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2765
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0293
_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/[\s^2^(Fo^2^)+(0.0519P)^2^+0.4185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                2723
_reflns_number_total             2765
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c0ob00919a.txt
_cod_data_source_block           j025
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7151776