Cu(I)-catalyzed reductive aldol cyclizations: diastereo- and enantioselective synthesis of beta-hydroxylactones.
Lam, Hon Wai; Joensuu, Pekka M.; Organic letters 7 (2005) 4225–4228; doi:10.1021/ol051649h

data_1506700
_publ_section_title
;
 Cu(I)-catalyzed reductive aldol cyclizations: diastereo- and
 enantioselective synthesis of beta-hydroxylactones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4225
_journal_page_last               4228
_journal_paper_doi               10.1021/ol051649h
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_compound_source        'Hon Lam, reaction PJC16A '
_chemical_formula_moiety         'C13 H15 Cl O3'
_chemical_formula_sum            'C13 H15 Cl O3'
_chemical_formula_weight         254.70
_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   mixed
_atom_sites_solution_primary     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_date             05-07-06
_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                   7.4180(2)
_cell_length_b                   9.0469(3)
_cell_length_c                   18.6730(6)
_cell_measurement_reflns_used    8623
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.5
_cell_volume                     1253.14(7)
_computing_cell_refinement       Saint
_computing_data_collection       Smart
_computing_data_reduction        Saint
_computing_molecular_graphics    XP
_computing_publication_material  'XCIF, PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Dirdif
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'Omega and phi'
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19493
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs v2.10'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
;
Solvent layering: petrol on top, Et2O on bottom.
;
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    'riding/rotating group (OH and Me)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0580P)^2^+0.0695P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                3151
_reflns_number_total             3595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051649hsi20050713_013201.cif
_cod_data_source_block           hl0508
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multiscan'
changed to 'multi-scan' 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 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom/difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1506700