Exploiting a "Beast" in Carbenoid Chemistry: Development of a Straightforward Direct Nucleophilic Fluoromethylation Strategy.
Parisi, Giovanna; Colella, Marco; Monticelli, Serena; Romanazzi, Giuseppe; Holzer, Wolfgang; Langer, Thierry; Degennaro, Leonardo; Pace, Vittorio; Luisi, Renzo; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b07891

data_4126411
_publ_section_title
;
 Exploiting a &quot;Beast&quot; in Carbenoid Chemistry: Development of a
 Straightforward Direct Nucleophilic Fluoromethylation Strategy.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b07891
_journal_year                    2017
_chemical_formula_moiety         'C13 H18 F N O2'
_chemical_formula_sum            'C13 H18 F N O2'
_chemical_formula_weight         239.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_date             2017-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                74.8164(8)
_cell_angle_beta                 85.3302(9)
_cell_angle_gamma                75.4550(8)
_cell_formula_units_Z            2
_cell_length_a                   5.3296(2)
_cell_length_b                   10.3296(3)
_cell_length_c                   12.0234(4)
_cell_measurement_reflns_used    8271
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.499
_cell_measurement_theta_min      3.810
_cell_volume                     618.25(4)
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_collection       'APEX 3'
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9859
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.492
_diffrn_reflns_theta_min         3.810
_diffrn_source                   'sealed xray tube'
_diffrn_source_type              'Incoatec IuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.7043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.0479 before and 0.0268 after correction. 
The Ratio of minimum to maximum transmission is 0.9346.
 The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0306P)^2^+0.3178P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             2445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07891_si_002.cif
_cod_data_source_block           cu_vipa_vdm39_p-1
_cod_database_code               4126411
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.892