2H-Azirines from a concerted addition of alkylcarbenes to nitrile groups.
Knoll, Wolfgang; Mieusset, Jean-Luc; Arion, Vladimir B.; Brecker, Lothar; Brinker, Udo H.; Organic letters 12 (2010) 2366–2369; doi:10.1021/ol100703r

data_1502979
_publ_section_title
;
 2H-Azirines from a concerted addition of alkylcarbenes to nitrile groups.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2366
_journal_page_last               2369
_journal_paper_doi               10.1021/ol100703r
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C10 H13 F N2'
_chemical_formula_sum            'C10 H13 F N2'
_chemical_formula_weight         180.22
_chemical_name_systematic
; 
4-Azi-1-fluoroadamantane 
;
_space_group_IT_number           106
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4c -2ab'
_symmetry_space_group_name_H-M   'P 42 b c'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.0215(4)
_cell_length_b                   14.0215(4)
_cell_length_c                   8.8612(3)
_cell_measurement_reflns_used    7503
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.30
_cell_measurement_theta_min      3.60
_cell_volume                     1742.13(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0116
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            68494
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1068
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.3802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                970
_reflns_number_total             1068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100703r_si_002.cif
_cod_data_source_block           wokn002
_cod_original_sg_symbol_H-M      P42bc
_cod_database_code               1502979