Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids.
Macabeo, Allan Patrick G.; Kreuzer, Andreas; Reiser, Oliver; Organic & biomolecular chemistry 9 (2011) 3146–3150; doi:10.1039/c1ob05113j

data_7151861
_publ_section_title
;
 Stereoselective routes to aryl substituted \g-butyrolactones and their
 application towards the synthesis of highly oxidised
 furanocembranoids.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3146
_journal_page_last               3150
_journal_paper_doi               10.1039/c1ob05113j
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C13 H20 O7'
_chemical_formula_sum            'C13 H20 O7'
_chemical_formula_weight         288.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.925(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8226(2)
_cell_length_b                   10.0497(2)
_cell_length_c                   9.1628(2)
_cell_measurement_reflns_used    5811
_cell_measurement_temperature    123
_cell_measurement_theta_max      66.6778
_cell_measurement_theta_min      4.3962
_cell_volume                     702.08(3)
_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)
;
_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 10.5431
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
1 omega -98.00 -18.00 1.6000 3.0000
omega____ theta____ kappa____ phi______ frames
- -40.3806 125.0000 -90.0000 50

2 omega 25.00 116.20 1.6000 3.0000
omega____ theta____ kappa____ phi______ frames
- 40.3806 37.0000 -180.0000 57

3 omega 21.00 115.40 1.6000 3.0000
omega____ theta____ kappa____ phi______ frames
- 40.3806 37.0000 90.0000 59

4 omega -77.00 -16.20 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- -90.0000 45.0000 120.0000 38

5 omega -119.00 -40.60 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- -90.0000 125.0000 -150.0000 49

6 omega -144.00 -12.80 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- -90.0000 15.0000 90.0000 82

7 omega 94.00 148.40 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- 93.7786 45.0000 -90.0000 34

8 omega 104.80 170.40 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- 93.7786 77.0000 0.0000 41

9 omega 65.00 105.00 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- 93.7786 77.0000 0.0000 25

10 omega 73.00 161.00 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- 93.7786 45.0000 60.0000 55

11 omega 77.80 167.40 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- 93.7786 125.0000 -60.0000 56

12 omega -98.00 -18.00 1.6000 3.0000
omega____ theta____ kappa____ phi______ frames
- -40.3806 125.0000 90.0000 50

13 omega -115.00 -11.00 1.6000 3.0000
omega____ theta____ kappa____ phi______ frames
- -40.3806 -66.0000 -16.0000 65

14 omega 7.00 119.00 1.6000 3.0000
omega____ theta____ kappa____ phi______ frames
- 40.3806 77.0000 -90.0000 70

15 omega -165.00 -61.00 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- -90.0000 -66.0000 -16.0000 65

16 omega -169.00 -57.00 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- -90.0000 -77.0000 -120.0000 70

17 omega 15.00 127.00 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- 93.7786 -77.0000 0.0000 70

18 omega 60.00 172.00 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- 93.7786 77.0000 90.0000 70

19 omega 60.00 69.60 1.6000 30.0000
omega____ theta____ kappa____ phi______ frames
- 93.7786 77.0000 150.0000 6

;
_diffrn_measurement_device_type
'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6700
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        66.79
_diffrn_reflns_theta_max         66.79
_diffrn_reflns_theta_min         4.95
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.864
_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    1.364
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.2359
_exptl_crystal_size_mid          0.1897
_exptl_crystal_size_min          0.1102
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2377
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0459P)^2^+0.1048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                2308
_reflns_number_total             2377
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c1ob05113j.txt
_cod_data_source_block           j031
_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      'P 21'
_cod_database_code               7151861