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_1502980
_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         'C14 H15 F N2'
_chemical_formula_sum            'C14 H15 F N2'
_chemical_formula_weight         230.28
_chemical_name_systematic
; 
3-(2-trans-Cyanoethenyl)-5'-fluoro-spiro[2-H-azirine-2,2'-
tricyclo[3.3.1.1^3',7'^]decane
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.081(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4202(3)
_cell_length_b                   27.8217(11)
_cell_length_c                   6.4690(2)
_cell_measurement_reflns_used    5959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.81
_cell_measurement_theta_min      3.33
_cell_volume                     1146.69(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            36316
_diffrn_reflns_theta_full        30.14
_diffrn_reflns_theta_max         30.14
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.9645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0373P)^2^+0.6626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                2876
_reflns_number_total             3358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100703r_si_002.cif
_cod_data_source_block           wokn001
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1502980