Highly Selective Catalyst-Dependent Competitive 1,2-C\ρightarrowC, -O\ρightarrowC, and -N\ρightarrowC Migrations from β-Methylene-β-silyloxy-β-amido-α-diazoacetates
Xichen Xu; Yu Qian; Peter Y. Zavalij; Michael P. Doyle; Journal of the American Chemical Society 135 (2013) 1244–1247; doi:10.1021/ja311392m

data_4119230
_publ_section_title
;
 Highly Selective Catalyst-Dependent Competitive 1,2-C\\rightarrowC,
 -O\\rightarrowC, and -N\\rightarrowC Migrations from
 \b-Methylene-\b-silyloxy-\b-amido-\a-diazoacetates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1244
_journal_page_last               1247
_journal_paper_doi               10.1021/ja311392m
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C21 H30 N4 O4 Si'
_chemical_formula_sum            'C21 H30 N4 O4 Si'
_chemical_formula_weight         430.58
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 & ZCIF'
_cell_angle_alpha                80.425(5)
_cell_angle_beta                 80.943(5)
_cell_angle_gamma                86.925(5)
_cell_formula_units_Z            2
_cell_length_a                   7.566(3)
_cell_length_b                   11.733(4)
_cell_length_c                   13.317(4)
_cell_measurement_reflns_used    8532
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     1150.7(7)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'Bruker Smart Apex II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0185209
_diffrn_orient_matrix_UB_12      -0.0012497
_diffrn_orient_matrix_UB_13      -0.0758398
_diffrn_orient_matrix_UB_21      0.0220335
_diffrn_orient_matrix_UB_22      -0.0856062
_diffrn_orient_matrix_UB_23      0.0130908
_diffrn_orient_matrix_UB_31      -0.1307619
_diffrn_orient_matrix_UB_32      -0.0121057
_diffrn_orient_matrix_UB_33      0.0033591
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16495
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       prism
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0044(9)
_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   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.01P)^2^+0.484P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                4493
_reflns_number_total             5276
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311392m_si_002.cif
_cod_data_source_block           2311
_cod_original_cell_volume        1150.7(6)
_cod_database_code               4119230