Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester.
Harsanyi, Antal; Sandford, Graham; Yufit, Dmitri S.; Howard, Judith Ak; Beilstein journal of organic chemistry 10 (2014) 1213–1219; doi:10.3762/bjoc.10.119

data_4029599
_publ_section_title
;
 Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives
 from diethyl 2-fluoromalonate ester.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1213
_journal_page_last               1219
_journal_paper_doi               10.3762/bjoc.10.119
_journal_volume                  10
_journal_year                    2014
_chemical_formula_moiety         'C6 H5 F N2 O2'
_chemical_formula_sum            'C6 H5 F N2 O2'
_chemical_formula_weight         156.12
_chemical_name_systematic        2-fluoromethyl-3-nitropyridine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-08-23
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.08.15 svn.r2450, GUI svn.r4314)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.767(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6568(3)
_cell_length_b                   15.4823(9)
_cell_length_c                   7.1654(4)
_cell_measurement_reflns_used    3154
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.89
_cell_measurement_theta_min      2.63
_cell_volume                     623.18(6)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10239
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         2.63
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'sealed X-ray tube'
_diffrn_source_voltage           20.0
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0452 before and 0.0319 after correction.
The Ratio of minimum to maximum transmission is 0.2991.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0750P)^2^+0.2500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1374
_reflns_number_total             1735
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-119-S3.cif
_cod_data_source_block           7_12srv159
_cod_depositor_comments
'Adding full bibliography for 4029597--4029599.cif.'
_cod_database_code               4029599