Diastereoselective intermolecular cobalt-catalyzed reductive aldol reactions of alpha,beta-unsaturated amides with ketones.
Lumby, Ralph J. R.; Joensuu, Pekka M.; Lam, Hon Wai; Organic letters 9 (2007) 4367–4370; doi:10.1021/ol701980e

data_1505570
_publ_section_title
;
 Diastereoselective intermolecular cobalt-catalyzed reductive aldol
 reactions of alpha,beta-unsaturated amides with ketones.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4367
_journal_page_last               4370
_journal_paper_doi               10.1021/ol701980e
_journal_volume                  9
_journal_year                    2007
_chemical_compound_source        'Ralph Lamby, RJL2/56MAD'
_chemical_formula_moiety         'C12 H23 N1 O3'
_chemical_formula_sum            'C12 H23 N O3'
_chemical_formula_weight         229.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-07-26
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 91.1620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   11.7337(2)
_cell_length_b                   17.5364(4)
_cell_length_c                   26.0481(5)
_cell_measurement_reflns_used    5013
_cell_measurement_temperature    150
_cell_measurement_theta_max      21
_cell_measurement_theta_min      2
_cell_volume                     5358.73(18)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47854
_diffrn_reflns_theta_full        23.255
_diffrn_reflns_theta_max         23.255
_diffrn_reflns_theta_min         1.889
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_recrystallization_method 'slow evaporation of hexane'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9462
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.000514
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 5.12 7.80 3.64 0.864 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1123
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.1123
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                3641
_reflns_number_total             7683
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.82
_oxford_diffrn_Wilson_scale      200.31
_oxford_refine_ls_scale          0.076842(16)
_oxford_structure_analysis_title 'hl7011 in P2(1)/n'
_cod_data_source_file            ol701980e-file004.cif
_cod_data_source_block           HL7011
_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      'P 1 21/n 1 '
_cod_original_formula_sum        'C12 H23 N1 O3'
_cod_database_code               1505570