CrCl~2~-Promoted Stereospecific and Stereoselective Alkyl- and Silylcyclopropanation of α,β-Unsaturated Amides
José M. Concellón; Humberto Rodríguez-Solla; Carmen Méjica; Elena G. Blanco; Santiago García-Granda; M. Rosario Díaz; Journal of Organic Chemistry 73 (2008) 3828–3836; doi:10.1021/jo800103t

data_4023407
_publ_contact_author
;     Santiago Garc\'ia-Granda
      Departamento de Qu\'imica F\'isica y Anal\'itica
      Facultad de Qu\'imica
      Universidad de Oviedo
      Avda. Juli\'an Claver\'ia, 8
      33071 Oviedo
      Spain
;
_publ_contact_author_email       sgg@uniovi.es
_publ_contact_author_fax         '0034 98 5103125'
_publ_contact_author_phone       '0034 98 5103477'
_publ_section_title
;
 CrCl~2~-Promoted Stereospecific and Stereoselective Alkyl- and
 Silylcyclopropanation of \a,\b-Unsaturated Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3828
_journal_page_last               3836
_journal_paper_doi               10.1021/jo800103t
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C22 H28 O Si'
_chemical_formula_sum            'C22 H28 O Si'
_chemical_formula_weight         336.55
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.000(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5059(3)
_cell_length_b                   6.17440(10)
_cell_length_c                   22.7859(4)
_cell_measurement_reflns_used    3374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69
_cell_measurement_theta_min      3
_cell_volume                     2039.58(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3374
_diffrn_reflns_theta_full        66.40
_diffrn_reflns_theta_max         66.40
_diffrn_reflns_theta_min         3.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.034
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
Cubic fit to sin(theta)/lambda - 24 parameters
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Absolute Configuration of C2 = S
 Absolute Configuration of C3 = R
 Absolute Configuration of C4 = S
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                1717
_reflns_number_total             3374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800103t-File002.cif
_cod_data_source_block           7d
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023407