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_4023406
_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         'C20 H39 N O Si'
_chemical_formula_sum            'C20 H39 N O Si'
_chemical_formula_weight         337.61
_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                 95.899(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.5294(8)
_cell_length_b                   11.6563(4)
_cell_length_c                   10.6108(4)
_cell_measurement_reflns_used    4709
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.13
_cell_measurement_theta_min      2.40
_cell_volume                     2279.63(15)
_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_measured_fraction_theta_full 0.780
_diffrn_measured_fraction_theta_max 0.780
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.09032
_diffrn_orient_matrix_UB_12      -0.00951
_diffrn_orient_matrix_UB_13      -0.02706
_diffrn_orient_matrix_UB_21      -0.00306
_diffrn_orient_matrix_UB_22      -0.07718
_diffrn_orient_matrix_UB_23      0.03734
_diffrn_orient_matrix_UB_31      -0.02154
_diffrn_orient_matrix_UB_32      0.02238
_diffrn_orient_matrix_UB_33      0.04450
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.1044
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4579
_diffrn_reflns_theta_full        61.11
_diffrn_reflns_theta_max         61.11
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    0.984
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                1387
_reflns_number_total             2721
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800103t-File001.cif
_cod_data_source_block           4g
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023406