A novel reaction of gem-difluorocyclopropyl ketones with nitriles leading to 2-fluoropyrroles
Tang-Po Yang; Jin-Hong Lin; Qing-Yun Chen; Ji-Chang Xiao; Chem.Commun. 49 (2013) 9833–; doi:10.1039/c3cc45456h

data_7109896
_publ_section_title
;
 A novel reaction of gem-difluorocyclopropyl ketones with nitriles leading
 to 2-fluoropyrroles
;
_journal_name_full               Chem.Commun.
_journal_page_first              9833
_journal_paper_doi               10.1039/c3cc45456h
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C12 H10 F N O'
_chemical_formula_weight         203.21
_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
_cell_angle_alpha                107.042(3)
_cell_angle_beta                 92.711(4)
_cell_angle_gamma                99.386(3)
_cell_formula_units_Z            4
_cell_length_a                   9.8897(16)
_cell_length_b                   9.8944(17)
_cell_length_c                   11.4945(18)
_cell_measurement_reflns_used    1191
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.414
_cell_measurement_theta_min      4.382
_cell_volume                     1055.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5581
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42585
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0024(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   0.833
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1527
_reflns_number_gt                1887
_reflns_number_total             3856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45456h.txt
_cod_data_source_block           cd201298
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7109896