Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates.
Xu, Xinfang; Shabashov, Dmitry; Zavalij, Peter Y.; Doyle, Michael P.; Organic letters 14 (2012) 800–803; doi:10.1021/ol203331r

data_1503594
_publ_section_title
;
 Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with
 Nitrile Oxides That Form 5-Arylaminofuran-2(3H)-one-4-carboxylates.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              800
_journal_page_last               803
_journal_paper_doi               10.1021/ol203331r
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C21 H33 N O5 Si'
_chemical_formula_sum            'C21 H33 N O5 Si'
_chemical_formula_weight         407.57
_chemical_name_common            Organic
_chemical_name_systematic
;
Organic
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 & ZCIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 94.5460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1773(9)
_cell_length_b                   9.1480(6)
_cell_length_c                   16.9630(10)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.7
_cell_measurement_theta_min      2.4
_cell_volume                     2347.8(2)
_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      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 11.198
_diffrn_detector_type            'Bruker Smart Apex II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      366,366,366,720
_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      0.0359491
_diffrn_orient_matrix_UB_12      -0.0674605
_diffrn_orient_matrix_UB_13      -0.0309652
_diffrn_orient_matrix_UB_21      -0.0501517
_diffrn_orient_matrix_UB_22      -0.0079357
_diffrn_orient_matrix_UB_23      -0.0417165
_diffrn_orient_matrix_UB_31      0.0236860
_diffrn_orient_matrix_UB_32      0.0856483
_diffrn_orient_matrix_UB_33      -0.0282524
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31875
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.41
_diffrn_source_current           30.00
_diffrn_source_voltage           50.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_id                'Doyle-Xu XXU-OX-3 150K'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.002
_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^+1.449P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0762
_reflns_number_gt                4427
_reflns_number_total             5376
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203331r_si_002.cif
_cod_data_source_block           2213
_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      P21/n
_cod_database_code               1503594
_diffrn_measurement_frame_width-ccd -0.5
_diffrn_measurement_total_frames-ccd 1818
_diffrn_measurement_frame_time-ccd 30
_diffrn_measurement_total_time-ccd 18.2
_diffrn_detector_distance-ccd    5.000
_diffrn_measurement_frame_size-ccd 512