Intermolecular Reactions of Foiled Carbenes with N-H Bonds: Evidence for an Ylidic Pathway
Jean-Luc Mieusset; Alexander Bespokoev; Mirjana Pacar; Michael Abraham; Vladimir B. Arion; Udo H. Brinker; Journal of Organic Chemistry 73 (2008) 6551–6558; doi:10.1021/jo800802m

data_4023630
_publ_section_title
;
 Intermolecular Reactions of Foiled Carbenes with N-H Bonds:
 Evidence for an Ylidic Pathway
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6551
_journal_page_last               6558
_journal_paper_doi               10.1021/jo800802m
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H20 N2 O2'
_chemical_formula_weight         248.32
_chemical_name_systematic
; 
rac-5-Methoxy-5-methylspiro[5H-[1,3,4]oxadiazole-2,11'-endo-tricyclo-
[6.2.1.0^2,7^]undec-9-ene]
;
_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                 108.656(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2956(3)
_cell_length_b                   23.4591(11)
_cell_length_c                   9.0064(4)
_cell_measurement_reflns_used    1468
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.37
_cell_measurement_theta_min      1.80
_cell_volume                     1260.26(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            32091
_diffrn_reflns_theta_full        25.82
_diffrn_reflns_theta_max         25.82
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.5332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                2203
_reflns_number_total             2412
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800802m-file004.cif
_cod_data_source_block           AW01
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023630