Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents.
Rudkin, Mairi E.; Joensuu, Pekka M.; MacLachlan, William S.; Lam, Hon Wai; Organic letters 10 (2008) 2939–2942; doi:10.1021/ol800883b

data_1504717
_publ_section_title
;
 Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using
 trialkylaluminum reagents.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2939
_journal_page_last               2942
_journal_paper_doi               10.1021/ol800883b
_journal_volume                  10
_journal_year                    2008
_chemical_compound_source        'Mairi Rudkin MRA143A'
_chemical_formula_moiety         'C22 H27 N1 O2'
_chemical_formula_sum            'C22 H27 N O2'
_chemical_formula_weight         337.46
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   'geom/difmap (OH)'
_atom_sites_solution_primary     direct
_audit_creation_date             07-06-22
_audit_creation_method           CRYSTALS_ver_12.83
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.8324(4)
_cell_length_b                   22.8044(15)
_cell_length_c                   23.4492(14)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    150
_cell_measurement_theta_max      19
_cell_measurement_theta_min      3
_cell_volume                     3653.6(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.085
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            35765
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         1.737
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00
_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    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method
;
Crystals were dissolved in a small amount of EtOAc and then layered
with hexane. Crystals grew after 3 days.
;
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9843
_refine_ls_hydrogen_treatment    noref/refall(OH)
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000431
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.26P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1001
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1001
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2194
_reflns_number_total             3211
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.58
_oxford_diffrn_Wilson_scale      0.68
_oxford_refine_ls_scale          1.266(6)
_oxford_structure_analysis_title 'hl7009 in Pbca'
_cod_data_source_file            ol800883b-file004.cif
_cod_data_source_block           hl7009
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P b c a '
_cod_original_formula_sum        'C22 H27 N1 O2'
_cod_database_code               1504717