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_1506125
_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        'P. Joensuu PJD784'
_chemical_formula_moiety         'C18 H21 N1 O3'
_chemical_formula_sum            'C18 H21 N O3'
_chemical_formula_weight         299.37
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             06-02-18
_audit_creation_method           CRYSTALS_ver_12.83
_cell_angle_alpha                90
_cell_angle_beta                 93.449(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0242(5)
_cell_length_b                   21.4235(19)
_cell_length_c                   11.8956(9)
_cell_measurement_reflns_used    3900
_cell_measurement_temperature    150
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1532.5(2)
_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  0.047
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13002
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.901
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
;
Diffusion of petrol into DCM soln
;
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8861
_refine_ls_hydrogen_treatment    'noref/refall (H21)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000287
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1018
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1018
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1899
_reflns_number_total             2709
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.5681(13)
_oxford_structure_analysis_title 'hl6001 in P2(1)/n'
_cod_data_source_file            ol061329dsi20060531_104544.cif
_cod_data_source_block           hl6001
_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 

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      P21/n
_cod_original_formula_sum        'C18 H21 N1 O3'
_cod_database_code               1506125