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_4029598
_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_absolute_configuration unk
_chemical_formula_moiety         'C9 H8 F N O4'
_chemical_formula_sum            'C9 H8 F N O4'
_chemical_formula_weight         213.16
_chemical_name_systematic
;
Methyl 2-fluoro-2-(2-nitrophenyl)acetate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2946(7)
_cell_length_b                   16.473(2)
_cell_length_c                   7.7761(11)
_cell_measurement_reflns_used    757
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.3602
_cell_measurement_theta_min      2.6140
_cell_volume                     934.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9881
_diffrn_measurement_details
;
  1 omega  -99.00  -71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -38.0000  120.0000 28

  2 omega  -58.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429   19.0000  120.0000 103

  3 omega  -72.00  -25.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  124.0000  -73.0000 47

  4 omega  -99.00  -19.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429  -19.0000  -60.0000 80
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      -0.0191723000
_diffrn_orient_matrix_UB_12      -0.0169070000
_diffrn_orient_matrix_UB_13      0.0818825000
_diffrn_orient_matrix_UB_21      0.0017476000
_diffrn_orient_matrix_UB_22      0.0393599000
_diffrn_orient_matrix_UB_23      0.0370129000
_diffrn_orient_matrix_UB_31      -0.0953117000
_diffrn_orient_matrix_UB_32      0.0041977000
_diffrn_orient_matrix_UB_33      -0.0158623000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_xray_symbol    Mo
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4548
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_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    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.4553
_exptl_crystal_size_mid          0.1647
_exptl_crystal_size_min          0.0329
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1207
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0450P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                874
_reflns_number_total             1207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-119-S3.cif
_cod_data_source_block           6a_12srv157
_cod_depositor_comments
'Adding full bibliography for 4029597--4029599.cif.'
_cod_database_code               4029598
_chemical_oxdiff_formula         'C9 H8 F1 N1 O4'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44