##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-07-13
_journal_date_accepted     2007-07-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      8
_journal_page_first     o3574
_journal_page_last     o3574
_journal_paper_category     QO
_journal_coeditor_code     TK2181
_publ_contact_author_name     'Sarah A. Barnett'
_publ_contact_author_address
;
Department of Chemistry
University College London
20 Gordon Street
London WC1H 0AJ
England
;
_publ_contact_author_email     sarah.barnett@ucl.ac.uk
_publ_contact_author_fax     '020 7679 7463'
_publ_contact_author_phone     '020 7679 4665'
_publ_section_title
;
7-Fluoroisatin--1,4-dioxane (1/1)
;
loop_
    _publ_author_name
    _publ_author_address
    'Shankland, Kenneth'
;
ISIS Facility
Rutherford Appleton Laboratory
Chilton
Didcot
Oxon OX11 0QX
England
;
    'Leech, Charlotte K.'
;
ISIS Facility
Rutherford Appleton Laboratory
Chilton
Didcot
Oxon OX11 0QX
England
;
    'Mohamed, Sharmarke'
;
Department of Chemistry
University College London
20 Gordon Street
London WC1H 0AJ
England
;
    'Barnett, Sarah A.'
;
Department of Chemistry
University College London
20 Gordon Street
London WC1H 0AJ
England
;
    'Tocher, Derek A.'
;
Department of Chemistry
University College London
20 Gordon Street
London WC1H 0AJ
England
;
data_I
_chemical_name_systematic
;
7-fluoroindoline-2,3-dione--1,4-dioxane (1/1)
;
_chemical_name_common     '7-Fluoroisatin--1,4-dioxane (1/1)'
_chemical_formula_moiety     'C12 H12 F N O4'
_chemical_formula_sum     'C12 H12 F N O4'
_chemical_formula_iupac     'C12 H12 F N O4'
_chemical_formula_weight     253.23
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     11.5274(3)
_cell_length_b     8.6508(2)
_cell_length_c     12.1738(4)
_cell_angle_alpha     90
_cell_angle_beta     106.701(3)
_cell_angle_gamma     90
_cell_volume     1162.78(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5725
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     28.6
_cell_measurement_temperature     123(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.447
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     0.119
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_absorpt_correction_T_min     0.960
_exptl_absorpt_correction_T_max     0.993
_exptl_special_details
;
;
_diffrn_ambient_temperature     123(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     16.0
_diffrn_reflns_number     12479
_diffrn_reflns_av_R_equivalents     0.041
_diffrn_reflns_av_sigmaI/netI     0.032
_diffrn_reflns_theta_min     2.9
_diffrn_reflns_theta_max     28.7
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.908
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2740
_reflns_number_gt     2042
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.062
_refine_ls_R_factor_gt     0.039
_refine_ls_wR_factor_gt     0.092
_refine_ls_wR_factor_ref     0.103
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     1.04
_refine_ls_number_reflns     2740
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.0555P)²+0.117P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     direct
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.30
_refine_diff_density_min     -0.16
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction     'CrysAlis RED'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
SHELXTL (Bruker, 2000) and Mercury (Macrae et al.,  2006)
;
_computing_publication_material     'SHELXL97 and PLATON (Spek 2003)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.63568(11) 0.30973(16) 0.41226(12) 0.0227(3) Uani d . 1 . .
    C C2 0.67610(11) 0.36091(17) 0.54023(12) 0.0241(3) Uani d . 1 . .
    C C3 0.65915(11) 0.52886(17) 0.53806(12) 0.0232(3) Uani d . 1 . .
    C C4 0.67938(13) 0.63897(19) 0.62395(13) 0.0288(3) Uani d . 1 . .
    H H1 0.7103(14) 0.606(2) 0.7033(15) 0.037(5) Uiso d . 1 . .
    C C5 0.65384(13) 0.79131(19) 0.59349(15) 0.0329(4) Uani d . 1 . .
    H H2 0.6680(14) 0.867(2) 0.6539(15) 0.038(5) Uiso d . 1 . .
    C C6 0.60940(13) 0.83359(18) 0.47911(15) 0.0318(4) Uani d . 1 . .
    H H3 0.5924(15) 0.937(2) 0.4561(15) 0.041(5) Uiso d . 1 . .
    C C7 0.59034(13) 0.72222(17) 0.39484(13) 0.0274(3) Uani d . 1 . .
    C C8 0.61464(11) 0.56981(16) 0.42251(12) 0.0215(3) Uani d . 1 . .
    N N1 0.60153(10) 0.44135(13) 0.35030(10) 0.0230(3) Uani d . 1 . .
    H H4 0.5719(16) 0.444(2) 0.2720(17) 0.048(5) Uiso d . 1 . .
    O O1 0.63342(9) 0.17947(11) 0.37651(9) 0.0302(3) Uani d . 1 . .
    O O2 0.71073(9) 0.27269(13) 0.61973(9) 0.0335(3) Uani d . 1 . .
    F F1 0.54700(9) 0.76186(11) 0.28272(8) 0.0414(3) Uani d . 1 . .
    C C9 0.38445(13) 0.47942(19) -0.07452(13) 0.0272(3) Uani d . 1 . .
    H H9A 0.3873(14) 0.370(2) -0.0935(13) 0.032(4) Uiso d . 1 . .
    H H9B 0.3077(14) 0.5267(18) -0.1169(13) 0.029(4) Uiso d . 1 . .
    C C10 0.40659(12) 0.50121(19) 0.05195(12) 0.0277(3) Uani d . 1 . .
    H H10A 0.3476(14) 0.4418(17) 0.0791(13) 0.030(4) Uiso d . 1 . .
    H H10B 0.4031(13) 0.610(2) 0.0727(13) 0.030(4) Uiso d . 1 . .
    O O3 0.52419(8) 0.44245(11) 0.11257(8) 0.0262(2) Uani d . 1 . .
    C C11 0.46557(12) 0.05248(19) 0.09413(13) 0.0270(3) Uani d . 1 . .
    H H11A 0.4396(14) -0.0409(19) 0.1234(13) 0.026(4) Uiso d . 1 . .
    H H11B 0.4563(13) 0.1403(18) 0.1444(13) 0.024(4) Uiso d . 1 . .
    C C12 0.59628(12) 0.03656(18) 0.09507(13) 0.0272(3) Uani d . 1 . .
    H H12A 0.6456(14) 0.0060(19) 0.1745(14) 0.031(4) Uiso d . 1 . .
    H H12B 0.6237(14) 0.135(2) 0.0700(14) 0.031(4) Uiso d . 1 . .
    O O4 0.60965(8) -0.08326(11) 0.01931(8) 0.0256(2) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0195(6) 0.0247(7) 0.0234(7) -0.0004(5) 0.0056(5) 0.0013(6)
    C2 0.0198(6) 0.0307(8) 0.0220(7) -0.0005(6) 0.0060(5) 0.0043(6)
    C3 0.0188(6) 0.0294(8) 0.0217(7) -0.0007(5) 0.0065(5) 0.0007(6)
    C4 0.0257(7) 0.0387(9) 0.0233(8) -0.0037(6) 0.0091(6) -0.0043(7)
    C5 0.0296(8) 0.0351(9) 0.0361(9) -0.0053(6) 0.0126(7) -0.0122(7)
    C6 0.0286(7) 0.0231(8) 0.0465(10) -0.0007(6) 0.0153(7) -0.0011(7)
    C7 0.0258(7) 0.0293(8) 0.0266(8) 0.0013(6) 0.0066(6) 0.0053(6)
    C8 0.0181(6) 0.0249(7) 0.0216(7) -0.0014(5) 0.0057(5) 0.0011(5)
    N1 0.0248(6) 0.0253(6) 0.0172(6) 0.0002(5) 0.0030(5) 0.0005(5)
    O1 0.0302(5) 0.0247(6) 0.0345(6) 0.0004(4) 0.0072(5) -0.0011(5)
    O2 0.0347(6) 0.0387(6) 0.0261(6) 0.0048(5) 0.0072(5) 0.0127(5)
    F1 0.0563(6) 0.0334(5) 0.0314(5) 0.0093(4) 0.0080(5) 0.0128(4)
    C9 0.0226(7) 0.0316(8) 0.0242(7) -0.0019(6) 0.0017(6) 0.0027(6)
    C10 0.0232(7) 0.0348(8) 0.0244(8) 0.0010(6) 0.0057(6) 0.0020(7)
    O3 0.0246(5) 0.0316(6) 0.0196(5) -0.0005(4) 0.0020(4) 0.0041(4)
    C11 0.0236(7) 0.0329(8) 0.0223(7) 0.0022(6) 0.0033(6) 0.0001(6)
    C12 0.0232(7) 0.0306(8) 0.0248(8) 0.0019(6) 0.0022(6) -0.0013(6)
    O4 0.0211(5) 0.0277(5) 0.0250(5) 0.0045(4) 0.0018(4) 0.0015(4)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C1 . 1.3600(18) ?
    N1 C8 . 1.3979(17) ?
    N1 H4 . 0.92(2) ?
    C1 O1 . 1.2056(17) ?
    C1 C2 . 1.5566(19) ?
    C2 O2 . 1.2068(16) ?
    C2 C3 . 1.465(2) ?
    C3 C4 . 1.384(2) ?
    C3 C8 . 1.3975(18) ?
    C4 C5 . 1.378(2) ?
    C4 H1 . 0.972(17) ?
    C5 C6 . 1.388(2) ?
    C5 H2 . 0.960(18) ?
    C6 C7 . 1.378(2) ?
    C6 H3 . 0.944(18) ?
    C7 F1 . 1.3558(17) ?
    C7 C8 . 1.370(2) ?
    O3 C9 3_665 1.4356(17) ?
    O3 C10 . 1.4373(16) ?
    C9 O3 3_665 1.4356(17) ?
    C9 C10 . 1.498(2) ?
    C9 H9A . 0.979(18) ?
    C9 H9B . 0.976(16) ?
    C10 H10A . 0.983(16) ?
    C10 H10B . 0.979(17) ?
    O4 C12 . 1.4250(17) ?
    O4 C11 3_655 1.4288(17) ?
    C11 O4 3_655 1.4288(17) ?
    C11 C12 . 1.5097(19) ?
    C11 H11A . 0.965(16) ?
    C11 H11B . 1.001(16) ?
    C12 H12A . 1.006(16) ?
    C12 H12B . 0.990(17) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C8 . . 110.80(12) ?
    C1 N1 H4 . . 123.9(12) ?
    C8 N1 H4 . . 125.3(12) ?
    O1 C1 N1 . . 127.55(13) ?
    O1 C1 C2 . . 126.61(13) ?
    N1 C1 C2 . . 105.82(11) ?
    O2 C2 C3 . . 130.79(14) ?
    O2 C2 C1 . . 123.89(13) ?
    C3 C2 C1 . . 105.31(11) ?
    C4 C3 C8 . . 121.30(14) ?
    C4 C3 C2 . . 132.56(13) ?
    C8 C3 C2 . . 106.14(12) ?
    C5 C4 C3 . . 118.59(15) ?
    C5 C4 H1 . . 122.6(10) ?
    C3 C4 H1 . . 118.8(10) ?
    C4 C5 C6 . . 120.72(15) ?
    C4 C5 H2 . . 117.8(10) ?
    C6 C5 H2 . . 121.5(10) ?
    C7 C6 C5 . . 119.78(15) ?
    C7 C6 H3 . . 118.0(11) ?
    C5 C6 H3 . . 122.2(11) ?
    F1 C7 C8 . . 118.76(13) ?
    F1 C7 C6 . . 120.42(13) ?
    C8 C7 C6 . . 120.82(14) ?
    C7 C8 C3 . . 118.78(13) ?
    C7 C8 N1 . . 129.28(13) ?
    C3 C8 N1 . . 111.93(12) ?
    C9 O3 C10 3_665 . 109.81(11) ?
    O3 C9 C10 3_665 . 110.37(11) ?
    O3 C9 H9A 3_665 . 107.6(9) ?
    C10 C9 H9A . . 110.9(9) ?
    O3 C9 H9B 3_665 . 105.6(9) ?
    C10 C9 H9B . . 110.5(9) ?
    H9A C9 H9B . . 111.6(13) ?
    O3 C10 C9 . . 109.89(12) ?
    O3 C10 H10A . . 106.5(9) ?
    C9 C10 H10A . . 110.5(9) ?
    O3 C10 H10B . . 108.1(9) ?
    C9 C10 H10B . . 112.2(9) ?
    H10A C10 H10B . . 109.5(13) ?
    C12 O4 C11 . 3_655 109.97(11) ?
    O4 C11 C12 3_655 . 110.58(12) ?
    O4 C11 H11A 3_655 . 110.3(9) ?
    C12 C11 H11A . . 109.6(9) ?
    O4 C11 H11B 3_655 . 108.0(8) ?
    C12 C11 H11B . . 110.3(8) ?
    H11A C11 H11B . . 108.1(13) ?
    O4 C12 C11 . . 110.78(12) ?
    O4 C12 H12A . . 107.1(9) ?
    C11 C12 H12A . . 108.6(9) ?
    O4 C12 H12B . . 109.0(10) ?
    C11 C12 H12B . . 109.0(9) ?
    H12A C12 H12B . . 112.4(13) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C8 N1 C1 O1 . . . . 178.58(13) ?
    C8 N1 C1 C2 . . . . -0.21(14) ?
    O1 C1 C2 O2 . . . . 0.1(2) ?
    N1 C1 C2 O2 . . . . 178.91(13) ?
    O1 C1 C2 C3 . . . . -178.55(13) ?
    N1 C1 C2 C3 . . . . 0.25(13) ?
    O2 C2 C3 C4 . . . . 1.7(3) ?
    C1 C2 C3 C4 . . . . -179.74(14) ?
    O2 C2 C3 C8 . . . . -178.72(14) ?
    C1 C2 C3 C8 . . . . -0.19(13) ?
    C8 C3 C4 C5 . . . . 0.5(2) ?
    C2 C3 C4 C5 . . . . 179.97(14) ?
    C3 C4 C5 C6 . . . . -0.4(2) ?
    C4 C5 C6 C7 . . . . 0.1(2) ?
    C5 C6 C7 F1 . . . . -179.98(13) ?
    C5 C6 C7 C8 . . . . 0.1(2) ?
    F1 C7 C8 C3 . . . . -179.91(11) ?
    C6 C7 C8 C3 . . . . 0.1(2) ?
    F1 C7 C8 N1 . . . . 0.1(2) ?
    C6 C7 C8 N1 . . . . -179.96(13) ?
    C4 C3 C8 C7 . . . . -0.33(19) ?
    C2 C3 C8 C7 . . . . -179.94(12) ?
    C4 C3 C8 N1 . . . . 179.69(12) ?
    C2 C3 C8 N1 . . . . 0.07(14) ?
    C1 N1 C8 C7 . . . . -179.89(14) ?
    C1 N1 C8 C3 . . . . 0.09(15) ?
    C9 O3 C10 C9 3_665 . . . 58.41(17) ?
    O3 C9 C10 O3 3_665 . . . -58.75(17) ?
    C11 O4 C12 C11 3_655 . . . 57.46(17) ?
    O4 C11 C12 O4 3_655 . . . -57.81(17) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H4 O3 . 0.92(2) 1.86(2) 2.7727(15) 175.3(17)
    C4 H1 O2 2_656 0.972(17) 2.535(17) 3.2262(18) 128.1(13)
