Diastereoselective cobalt-catalyzed reductive aldol cyclizations using diethylzinc as the stoichiometric reductant.
Lam, Hon Wai; Joensuu, Pekka M.; Murray, Gordon J.; Fordyce, Euan A. F.; Prieto, Oscar; Luebbers, Thomas; Organic letters 8 (2006) 3729–3732; doi:10.1021/ol061329d

data_1506127
_publ_section_title
;
 Diastereoselective cobalt-catalyzed reductive aldol cyclizations using
 diethylzinc as the stoichiometric reductant.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3729
_journal_page_last               3732
_journal_paper_doi               10.1021/ol061329d
_journal_volume                  8
_journal_year                    2006
_chemical_compound_source        'Euan Fordyce EAFF21002A'
_chemical_formula_moiety         'C19 H25 N1 O5'
_chemical_formula_sum            'C19 H25 N O5'
_chemical_formula_weight         347.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   'geom/difmap (H12)'
_atom_sites_solution_primary     direct
_audit_creation_date             06-05-16
_audit_creation_method           CRYSTALS_ver_12.83
_cell_angle_alpha                90
_cell_angle_beta                 93.852(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8348(5)
_cell_length_b                   6.7889(3)
_cell_length_c                   21.2326(11)
_cell_measurement_reflns_used    4696
_cell_measurement_temperature    150
_cell_measurement_theta_max      31
_cell_measurement_theta_min      2
_cell_volume                     1702.09(14)
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4820
_diffrn_reflns_theta_full        28.133
_diffrn_reflns_theta_max         30.580
_diffrn_reflns_theta_min         1.923
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method
;
evaporation of soln in ethylacetate/pet ether
;
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000444
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1351
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1351
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                2795
_reflns_number_total             4820
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.54
_oxford_diffrn_Wilson_scale      3.75
_oxford_refine_ls_scale          0.5654(15)
_oxford_structure_analysis_title 'hl6003 in P2(1)/c'
_cod_data_source_file            ol061329dsi20060531_104624.cif
_cod_data_source_block           hl6003
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_sum        'C19 H25 N1 O5'
_cod_database_code               1506127