Diastereoselectivity Control of the Radical Carboazidation of Substituted Methylenecyclohexanes
Sylvaine Cren; Pascal Schär; Philippe Renaud; Kurt Schenk; Journal of Organic Chemistry 74 (2009) 2942–2946; doi:10.1021/jo900088x

data_4024471
_publ_section_title
;
Diastereoselectivity Control of the Radical Carboazidation of Substituted
Methylenecyclohexanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2942
_journal_page_last               2946
_journal_paper_doi               10.1021/jo900088x
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H41 N O4 Si'
_chemical_formula_sum            'C22 H41 N O4 Si'
_chemical_formula_weight         411.65
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Kurt J. Schenk'
_audit_contact_author_address
;
   Kurt J. Schenk
   LCr1 - IPMC - FSB - EPFL
   Le Cubtron, Bureau 521
   Dorigny
   CH-1015 Lausanne
;
_audit_contact_author_email      Kurt.Schenk@EPFL.CH
_audit_contact_author_fax        '+41 (0)21 693 0504'
_audit_contact_author_phone      '+41 (0)21 693 0635'
_audit_creation_date             '2nd February 2008'
_audit_creation_method           'SHELXL-97 & Stoe X-Red'
_cell_angle_alpha                90.00
_cell_angle_beta                 108.470(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.787(3)
_cell_length_b                   6.7761(4)
_cell_length_c                   29.664(3)
_cell_measurement_reflns_used    18682
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      1.60
_cell_volume                     5107.0(9)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'SHELXtl (Bruker, 1996)'
_computing_publication_material  'SHELXtl (Bruker, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      ' 180 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            22452
_diffrn_reflns_theta_full        29.19
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         1.60
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.20
_diffrn_source_voltage           55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Stoe, X_Red32, Version 1.31 (2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.201
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         6821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0806P)^2^+2.0694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1753
_reflns_number_gt                4943
_reflns_number_total             6821
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900088x_si_003.cif
_cod_data_source_block           SC5n
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4024471