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_1504718
_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        ' MRA177A '
_chemical_formula_moiety         'C23 H29 N1 O2'
_chemical_formula_sum            'C23 H29 N O2'
_chemical_formula_weight         351.49
_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
_atom_sites_solution_primary     direct
_audit_creation_date             07-06-25
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 93.330(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.039(2)
_cell_length_b                   22.635(4)
_cell_length_c                   14.321(3)
_cell_measurement_reflns_used    1924
_cell_measurement_temperature    150
_cell_measurement_theta_max      18
_cell_measurement_theta_min      2
_cell_volume                     3895.9(12)
_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 0.992
_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  0.162
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            63706
_diffrn_reflns_theta_full        25.959
_diffrn_reflns_theta_max         26.489
_diffrn_reflns_theta_min         0.900
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_recrystallization_method
; 
Crystals dissolved in DCM in a small vial containing petroleum ether,
sealed and left for a week. 
;
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0522
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000155
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.03P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1138
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0671
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4006
_reflns_number_total             14735
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.87
_oxford_diffrn_Wilson_scale      186.98
_oxford_refine_ls_scale          0.3712(9)
_oxford_structure_analysis_title 'hl7007 in P2(1)/c'
_cod_data_source_file            ol800883b-file005.cif
_cod_data_source_block           HL7007_cif
_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/c 1 '
_cod_original_formula_sum        'C23 H29 N1 O2'
_cod_database_code               1504718