#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:36:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178474 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/95/4029597.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4029597
loop_
_publ_author_name
'Harsanyi, Antal'
'Sandford, Graham'
'Yufit, Dmitri S.'
'Howard, Judith Ak'
_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         'C13 H14 F N O6'
_chemical_formula_sum            'C13 H14 F N O6'
_chemical_formula_weight         299.25
_chemical_name_systematic
;
Diethyl 2-fluoro-2-(2-nitrophenyl)-malonate
;
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-08-22
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.08.15 svn.r2450, GUI svn.r4314)
;
_cell_angle_alpha                88.846(19)
_cell_angle_beta                 76.201(17)
_cell_angle_gamma                66.218(17)
_cell_formula_units_Z            2
_cell_length_a                   7.6353(11)
_cell_length_b                   8.0212(17)
_cell_length_c                   12.559(3)
_cell_measurement_reflns_used    718
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.4547
_cell_measurement_theta_min      2.7796
_cell_volume                     681.0(3)
_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
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9952
_diffrn_measurement_details
;
  1 omega  -83.00  -34.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429 -179.0000   90.0000 49

  2 omega  -36.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429   38.0000   30.0000 80

  3 omega  -91.00   31.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3429    0.0000    0.0000 122

  4 omega   27.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -130.0000 -148.0000 60

  5 omega   61.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  179.0000    0.0000 36

  6 omega   62.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  179.0000 -180.0000 39

  7 omega   28.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -130.0000   31.0000 57
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ω-scan
_diffrn_orient_matrix_UB_11      -0.0282942000
_diffrn_orient_matrix_UB_12      -0.0700124000
_diffrn_orient_matrix_UB_13      0.0222959000
_diffrn_orient_matrix_UB_21      0.0119822000
_diffrn_orient_matrix_UB_22      -0.0351533000
_diffrn_orient_matrix_UB_23      -0.0538796000
_diffrn_orient_matrix_UB_31      0.1002970000
_diffrn_orient_matrix_UB_32      -0.0571800000
_diffrn_orient_matrix_UB_33      -0.0026464000
_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  0.0675
_diffrn_reflns_av_unetI/netI     0.1136
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5758
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.969
_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    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.2277
_exptl_crystal_size_min          0.0459
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0733
_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/[σ²(Fo²)+(0.0660P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1932
_reflns_number_gt                1811
_reflns_number_total             3284
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-119-S3.cif
_cod_data_source_block           3_12srv156
_cod_depositor_comments
'Adding full bibliography for 4029597--4029599.cif.'
_cod_original_cell_volume        681.0(2)
_cod_database_code               4029597
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C13 H14 F1 N1 O6'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
F1 F 0.3019(2) 0.2055(2) 0.25418(16) 0.0340(5) Uani 1 1 d
O1 O 0.0971(3) 0.4935(3) 0.1558(2) 0.0407(6) Uani 1 1 d
O2 O 0.3075(5) 0.4789(4) 0.0043(3) 0.0736(10) Uani 1 1 d
O3 O 0.3403(3) -0.1246(3) 0.3130(2) 0.0397(6) Uani 1 1 d
O4 O 0.0143(3) -0.0382(3) 0.32825(18) 0.0302(5) Uani 1 1 d
O5 O -0.0689(3) 0.3865(3) 0.37737(19) 0.0330(6) Uani 1 1 d
O6 O -0.1800(3) 0.3146(3) 0.24137(17) 0.0264(5) Uani 1 1 d
N1 N 0.2077(4) 0.4148(4) 0.0685(3) 0.0382(7) Uani 1 1 d
C1 C 0.1949(4) 0.1126(4) 0.1130(2) 0.0220(6) Uani 1 1 d
C2 C 0.2228(4) 0.2327(4) 0.0351(3) 0.0287(7) Uani 1 1 d
C3 C 0.2625(4) 0.1921(5) -0.0766(3) 0.0354(8) Uani 1 1 d
C4 C 0.2742(4) 0.0255(5) -0.1150(3) 0.0322(8) Uani 1 1 d
C5 C 0.2513(4) -0.0972(5) -0.0407(3) 0.0301(8) Uani 1 1 d
C6 C 0.2145(4) -0.0564(4) 0.0711(3) 0.0253(7) Uani 1 1 d
C7 C 0.1583(4) 0.1516(4) 0.2347(3) 0.0253(7) Uani 1 1 d
C8 C 0.1860(5) -0.0221(4) 0.2970(3) 0.0279(7) Uani 1 1 d
C9 C 0.0160(6) -0.1981(5) 0.3873(3) 0.0358(8) Uani 1 1 d
C10 C -0.1941(6) -0.1731(6) 0.4309(4) 0.0427(9) Uani 1 1 d
C11 C -0.0429(4) 0.3024(4) 0.2936(3) 0.0256(7) Uani 1 1 d
C12 C -0.3832(5) 0.4406(5) 0.2971(3) 0.0329(8) Uani 1 1 d
C13 C -0.4752(5) 0.3526(5) 0.3870(3) 0.0330(8) Uani 1 1 d
H3 H 0.282(5) 0.283(6) -0.131(3) 0.052(11) Uiso 1 1 d
H4 H 0.297(4) 0.006(4) -0.194(3) 0.023(8) Uiso 1 1 d
H5 H 0.273(5) -0.220(5) -0.064(3) 0.036(10) Uiso 1 1 d
H6 H 0.201(5) -0.148(5) 0.122(3) 0.035(9) Uiso 1 1 d
H9A H 0.094(5) -0.221(5) 0.445(3) 0.036(9) Uiso 1 1 d
H9B H 0.103(5) -0.310(5) 0.327(3) 0.040(10) Uiso 1 1 d
H10A H -0.266(5) -0.162(5) 0.371(3) 0.052(12) Uiso 1 1 d
H10B H -0.287(6) -0.062(6) 0.483(3) 0.067(13) Uiso 1 1 d
H10C H -0.183(6) -0.289(7) 0.472(4) 0.076(14) Uiso 1 1 d
H12A H -0.440(4) 0.463(4) 0.240(3) 0.027(9) Uiso 1 1 d
H12B H -0.378(4) 0.553(5) 0.322(3) 0.032(9) Uiso 1 1 d
H13A H -0.624(6) 0.432(5) 0.420(3) 0.055(11) Uiso 1 1 d
H13B H -0.404(6) 0.308(6) 0.443(3) 0.066(13) Uiso 1 1 d
H13C H -0.469(6) 0.232(6) 0.361(3) 0.066(13) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0229 0.0005 -0.0022 1.0002 0.0224 -0.0538 -0.0025
0 0 -1 0.0229 -0.0005 0.0022 -1.0002 -0.0224 0.0538 0.0025
1 0 0 0.1042 0.9984 0.0036 -0.0132 -0.0288 0.0125 0.1000
-1 0 0 0.1042 -0.9984 -0.0036 0.0132 0.0288 -0.0125 -0.1000
5 11 2 0.1604 4.9954 10.9877 2.0593 -0.8647 -0.4374 -0.1327
-5 -11 -2 0.1504 -4.9954 -10.9877 -2.0593 0.8647 0.4374 0.1327
6 -6 2 0.1214 5.9899 -5.9684 1.8534 0.2897 0.1817 0.9371
-8 -10 -4 0.1558 -7.9913 -9.9966 -4.0089 0.8366 0.4717 -0.2193
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O4 C9 116.6(2)
C11 O6 C12 115.1(2)
O1 N1 O2 123.6(3)
O1 N1 C2 119.2(3)
O2 N1 C2 117.2(3)
C2 C1 C6 116.1(3)
C2 C1 C7 123.8(3)
C6 C1 C7 120.0(3)
C1 C2 N1 121.5(3)
C3 C2 N1 115.6(3)
C3 C2 C1 123.0(3)
C2 C3 C4 119.3(3)
C2 C3 H3 121(2)
C4 C3 H3 120(2)
C3 C4 H4 116(2)
C5 C4 C3 119.2(3)
C5 C4 H4 125(2)
C4 C5 C6 121.1(3)
C4 C5 H5 122(2)
C6 C5 H5 117(2)
C1 C6 H6 120(2)
C5 C6 C1 121.3(3)
C5 C6 H6 119(2)
F1 C7 C1 109.1(2)
F1 C7 C8 104.5(2)
F1 C7 C11 106.1(2)
C1 C7 C8 112.0(2)
C1 C7 C11 116.7(2)
C11 C7 C8 107.5(2)
O3 C8 O4 126.4(3)
O3 C8 C7 123.9(3)
O4 C8 C7 109.8(2)
O4 C9 C10 107.7(3)
O4 C9 H9A 112(2)
O4 C9 H9B 103(2)
C10 C9 H9A 114(2)
C10 C9 H9B 114.8(19)
H9A C9 H9B 104(3)
C9 C10 H10A 113(2)
C9 C10 H10B 118(3)
C9 C10 H10C 104(2)
H10A C10 H10B 102(3)
H10A C10 H10C 111(3)
H10B C10 H10C 109(3)
O5 C11 O6 126.6(3)
O5 C11 C7 123.0(3)
O6 C11 C7 110.3(2)
O6 C12 C13 111.2(3)
O6 C12 H12A 101(2)
O6 C12 H12B 107.4(18)
C13 C12 H12A 113(2)
C13 C12 H12B 114(2)
H12A C12 H12B 109(3)
C12 C13 H13A 112(2)
C12 C13 H13B 115(3)
C12 C13 H13C 113(2)
H13A C13 H13B 112(3)
H13A C13 H13C 105(3)
H13B C13 H13C 97(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C7 1.401(3)
O1 N1 1.212(4)
O2 N1 1.225(4)
O3 C8 1.196(4)
O4 C8 1.334(4)
O4 C9 1.465(4)
O5 C11 1.193(3)
O6 C11 1.334(3)
O6 C12 1.471(4)
N1 C2 1.479(4)
C1 C2 1.400(4)
C1 C6 1.402(4)
C1 C7 1.503(4)
C2 C3 1.379(5)
C3 C4 1.391(5)
C3 H3 1.02(4)
C4 C5 1.376(5)
C4 H4 0.96(3)
C5 C6 1.383(5)
C5 H5 0.97(4)
C6 H6 0.98(4)
C7 C8 1.547(4)
C7 C11 1.538(4)
C9 C10 1.496(5)
C9 H9A 1.01(3)
C9 H9B 1.06(3)
C10 H10A 1.01(4)
C10 H10B 1.00(4)
C10 H10C 1.04(5)
C12 C13 1.502(5)
C12 H12A 0.90(3)
C12 H12B 0.98(3)
C13 H13A 1.03(4)
C13 H13B 0.97(4)
C13 H13C 1.00(5)
