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_4028175
_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_sum            'C9 H6 F2 N2 O2'
_chemical_formula_weight         212.16
_chemical_name_systematic
; 
 ? 
;
_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                 98.920(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0878(7)
_cell_length_b                   6.1470(6)
_cell_length_c                   19.9237(19)
_cell_measurement_reflns_used    6067
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.91
_cell_volume                     857.55(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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12618
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.9656
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.041(5)
_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   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0611P)^2^+0.1776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                1666
_reflns_number_total             1944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400381a_si_002.cif
_cod_data_source_block           ohj240_0m
_cod_database_code               4028175