Dihydroxylation-Based Approach for the Asymmetric Syntheses of Hydroxy-γ-butyrolactones
Jennifer Peed; Iwan R. Davies; Lucy R. Peacock; James E. Taylor; Gabriele Kociok-Köhn; Steven D. Bull; Journal of Organic Chemistry 77 (2012) 543–555; doi:10.1021/jo2021289

data_4026867
_publ_section_title
;
 Dihydroxylation-Based Approach for the Asymmetric Syntheses of
 Hydroxy-\g-butyrolactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              543
_journal_page_last               555
_journal_paper_doi               10.1021/jo2021289
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_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                   5.8808(2)
_cell_length_b                   11.1665(2)
_cell_length_c                   21.9865(6)
_cell_measurement_reflns_used    33274
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1443.81(7)
_computing_cell_refinement       'HKL Scalepack (Otwinski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of x-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
 SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). 
 Sheldrick, G.M., Instit\"ut f\"ur Anorganische Chemie der Universit\"at, 
 Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998 
;
_computing_structure_solution
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '492 1.1 degree images with \f and \w scans'
_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  0.0834
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19206
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.71
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                2797
_reflns_number_total             3314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2021289_si_002.cif
_cod_data_source_block           h11sdb11
_cod_database_code               4026867