Synthesis of 4-Fluoromethylsydnones and their Participation in Alkyne Cycloaddition Reactions
Robert S. Foster; Harry Adams; Harald Jakobi; Joseph P. A. Harrity; Journal of Organic Chemistry 78 (2013) 4049–4064; doi:10.1021/jo400381a

data_4028174
_publ_section_title
;
 Synthesis of 4-Fluoromethylsydnones and their Participation in Alkyne
 Cycloaddition Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4049
_journal_page_last               4064
_journal_paper_doi               10.1021/jo400381a
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C9 H5 F3 N2 O2'
_chemical_formula_sum            'C9 H5 F3 N2 O2'
_chemical_formula_weight         230.15
_chemical_name_systematic
; 
 ? 
;
_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                 99.698(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3420(7)
_cell_length_b                   6.2293(6)
_cell_length_c                   19.9999(14)
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.82
_cell_volume                     901.63(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3927
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0914P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                1683
_reflns_number_total             2044
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400381a_si_001.cif
_cod_data_source_block           rf1_1_0m
_cod_database_code               4028174