##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-[(6-Fluoro-1,3-benzothiazol-2-ylamino)methylene]-2,2-dimethyl-1,3-dioxane-
4,6-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 F N2 O4 S'
_chemical_formula_sum     'C14 H11 F N2 O4 S'
_chemical_formula_iupac     'C14 H11 F N2 O4 S'
_chemical_formula_weight     322.31
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_HALL     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     6.4330(10)
_cell_length_b     19.532(2)
_cell_length_c     11.218(2)
_cell_angle_alpha     90
_cell_angle_beta     102.520(10)
_cell_angle_gamma     90
_cell_volume     1376.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     4.6
_cell_measurement_theta_max     18.6
_cell_measurement_temperature     299(2)
_exptl_crystal_description     'rod'
_exptl_crystal_colour     'light brown'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.556
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     2.412
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     299(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2707
_diffrn_reflns_av_R_equivalents     0.024
_diffrn_reflns_av_sigmaI/netI     0.033
_diffrn_reflns_theta_min     4.5
_diffrn_reflns_theta_max     67.0
_diffrn_reflns_theta_full     67.0
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     1
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     2.0
_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     2454
_reflns_number_gt     1949
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.053
_refine_ls_R_factor_gt     0.035
_refine_ls_wR_factor_gt     0.086
_refine_ls_wR_factor_ref     0.094
_refine_ls_goodness_of_fit_ref     1.01
_refine_ls_restrained_S_all     1.01
_refine_ls_number_reflns     2454
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refxyz
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.047P)²+0.3778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.26
_refine_diff_density_min     -0.21
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0043(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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'
    'F' 'F' 0.0727 0.0534
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.3331 0.5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4-PC (Enraf--Nonius, 1993)'
_computing_cell_refinement     CAD-4-PC
_computing_data_reduction     'REDU4 (Stoe & Cie, 1987)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97'
loop_
    _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
    _atom_site_type_symbol
    S1 1.07160(8) -0.04044(3) 0.17716(5) 0.04063(18) Uani d . 1 . . S
    F1 1.8327(2) -0.07862(8) 0.42808(16) 0.0694(5) Uani d . 1 . . F
    O1 0.2004(2) 0.16178(7) -0.03010(14) 0.0392(4) Uani d . 1 . . O
    O2 0.3669(2) 0.26855(7) 0.02415(13) 0.0383(4) Uani d . 1 . . O
    O3 0.3780(2) 0.06384(7) 0.00090(14) 0.0436(4) Uani d . 1 . . O
    O4 0.6901(2) 0.27516(8) 0.13867(16) 0.0506(4) Uani d . 1 . . O
    N1 1.1530(3) 0.08694(8) 0.23835(16) 0.0380(4) Uani d . 1 . . N
    N2 0.8093(3) 0.06921(9) 0.11746(16) 0.0351(4) Uani d . 1 . . N
    H2N 0.713(4) 0.0399(12) 0.077(2) 0.042 Uiso d . 1 . . H
    C1 1.0102(3) 0.04631(10) 0.17900(17) 0.0328(4) Uani d . 1 . . C
    C2 1.3199(3) -0.02079(10) 0.26628(18) 0.0346(5) Uani d . 1 . . C
    C3 1.4860(4) -0.06573(12) 0.3119(2) 0.0431(5) Uani d . 1 . . C
    H3 1.472(4) -0.1130(13) 0.299(2) 0.052 Uiso d . 1 . . H
    C4 1.6666(3) -0.03659(12) 0.3804(2) 0.0462(6) Uani d . 1 . . C
    C5 1.6894(4) 0.03252(13) 0.4055(2) 0.0496(6) Uani d . 1 . . C
    H5 1.813(4) 0.0473(14) 0.453(2) 0.060 Uiso d . 1 . . H
    C6 1.5216(4) 0.07608(12) 0.3606(2) 0.0458(6) Uani d . 1 . . C
    H6 1.539(4) 0.1247(13) 0.380(2) 0.055 Uiso d . 1 . . H
    C7 1.3344(3) 0.04932(10) 0.28938(18) 0.0347(4) Uani d . 1 . . C
    C8 0.7609(3) 0.13532(11) 0.11482(19) 0.0348(5) Uani d . 1 . . C
    H8 0.874(4) 0.1655(12) 0.153(2) 0.042 Uiso d . 1 . . H
    C9 0.5699(3) 0.16531(10) 0.06328(18) 0.0336(5) Uani d . 1 . . C
    C10 0.3831(3) 0.12567(10) 0.00861(18) 0.0331(4) Uani d . 1 . . C
    C11 0.2185(3) 0.23168(10) -0.06809(19) 0.0344(5) Uani d . 1 . . C
    C12 0.5542(3) 0.23906(10) 0.07853(18) 0.0351(5) Uani d . 1 . . C
    C13 0.0058(4) 0.26480(13) -0.0743(3) 0.0463(6) Uani d . 1 . . C
    H13A -0.028(4) 0.2620(13) 0.006(3) 0.056 Uiso d . 1 . . H
    H13B -0.099(4) 0.2411(13) -0.135(2) 0.056 Uiso d . 1 . . H
    H13C 0.013(4) 0.3128(14) -0.097(2) 0.056 Uiso d . 1 . . H
    C14 0.2891(5) 0.23293(13) -0.1872(2) 0.0482(6) Uani d . 1 . . C
    H14A 0.281(4) 0.2825(14) -0.219(2) 0.058 Uiso d . 1 . . H
    H14B 0.434(4) 0.2158(14) -0.176(2) 0.058 Uiso d . 1 . . H
    H14C 0.192(4) 0.2091(14) -0.244(2) 0.058 Uiso d . 1 . . H
_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
    S1 C2 . 1.734(2) ?
    S1 C1 . 1.741(2) ?
    F1 C4 . 1.362(2) ?
    O1 C10 . 1.358(2) ?
    O1 C11 . 1.442(2) ?
    O2 C12 . 1.356(2) ?
    O2 C11 . 1.439(2) ?
    O3 C10 . 1.211(2) ?
    O4 C12 . 1.209(2) ?
    N1 C1 . 1.285(3) ?
    N1 C7 . 1.393(3) ?
    N2 C8 . 1.327(3) ?
    N2 C1 . 1.400(2) ?
    N2 H2N . 0.89(2) ?
    C2 C3 . 1.391(3) ?
    C2 C7 . 1.393(3) ?
    C3 C4 . 1.370(3) ?
    C3 H3 . 0.94(3) ?
    C4 C5 . 1.380(3) ?
    C5 C6 . 1.381(3) ?
    C5 H5 . 0.90(3) ?
    C6 C7 . 1.394(3) ?
    C6 H6 . 0.98(3) ?
    C8 C9 . 1.371(3) ?
    C8 H8 . 0.96(2) ?
    C9 C10 . 1.449(3) ?
    C9 C12 . 1.457(3) ?
    C11 C13 . 1.501(3) ?
    C11 C14 . 1.502(3) ?
    C13 H13A . 0.97(3) ?
    C13 H13B . 0.97(3) ?
    C13 H13C . 0.98(3) ?
    C14 H14A . 1.03(3) ?
    C14 H14B . 0.97(3) ?
    C14 H14C . 0.91(3) ?
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
    C2 S1 C1 . . 87.75(9) ?
    C10 O1 C11 . . 117.79(15) ?
    C12 O2 C11 . . 119.81(15) ?
    C1 N1 C7 . . 109.16(17) ?
    C8 N2 C1 . . 120.59(18) ?
    C8 N2 H2N . . 118.5(15) ?
    C1 N2 H2N . . 120.9(15) ?
    N1 C1 N2 . . 122.53(18) ?
    N1 C1 S1 . . 117.96(15) ?
    N2 C1 S1 . . 119.51(14) ?
    C3 C2 C7 . . 122.46(19) ?
    C3 C2 S1 . . 127.61(17) ?
    C7 C2 S1 . . 109.93(15) ?
    C4 C3 C2 . . 115.7(2) ?
    C4 C3 H3 . . 122.5(15) ?
    C2 C3 H3 . . 121.7(15) ?
    F1 C4 C3 . . 117.9(2) ?
    F1 C4 C5 . . 118.0(2) ?
    C3 C4 C5 . . 124.1(2) ?
    C4 C5 C6 . . 119.2(2) ?
    C4 C5 H5 . . 118.2(18) ?
    C6 C5 H5 . . 122.5(18) ?
    C5 C6 C7 . . 119.2(2) ?
    C5 C6 H6 . . 118.4(15) ?
    C7 C6 H6 . . 122.4(15) ?
    N1 C7 C2 . . 115.20(18) ?
    N1 C7 C6 . . 125.48(19) ?
    C2 C7 C6 . . 119.31(19) ?
    N2 C8 C9 . . 127.56(19) ?
    N2 C8 H8 . . 115.9(13) ?
    C9 C8 H8 . . 116.6(13) ?
    C8 C9 C10 . . 122.38(18) ?
    C8 C9 C12 . . 116.84(18) ?
    C10 C9 C12 . . 120.38(18) ?
    O3 C10 O1 . . 119.12(18) ?
    O3 C10 C9 . . 124.78(18) ?
    O1 C10 C9 . . 116.01(17) ?
    O2 C11 O1 . . 110.15(15) ?
    O2 C11 C13 . . 105.87(17) ?
    O1 C11 C13 . . 106.89(18) ?
    O2 C11 C14 . . 110.49(18) ?
    O1 C11 C14 . . 109.72(18) ?
    C13 C11 C14 . . 113.6(2) ?
    O4 C12 O2 . . 117.93(18) ?
    O4 C12 C9 . . 125.61(19) ?
    O2 C12 C9 . . 116.40(17) ?
    C11 C13 H13A . . 108.6(15) ?
    C11 C13 H13B . . 108.5(15) ?
    H13A C13 H13B . . 111(2) ?
    C11 C13 H13C . . 109.2(16) ?
    H13A C13 H13C . . 109(2) ?
    H13B C13 H13C . . 110(2) ?
    C11 C14 H14A . . 108.9(14) ?
    C11 C14 H14B . . 110.4(15) ?
    H14A C14 H14B . . 110(2) ?
    C11 C14 H14C . . 108.5(17) ?
    H14A C14 H14C . . 105(2) ?
    H14B C14 H14C . . 114(2) ?
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
    C7 N1 C1 N2 . . . . 179.95(18) ?
    C7 N1 C1 S1 . . . . 0.4(2) ?
    C8 N2 C1 N1 . . . . 2.3(3) ?
    C8 N2 C1 S1 . . . . -178.18(17) ?
    C2 S1 C1 N1 . . . . -0.25(18) ?
    C2 S1 C1 N2 . . . . -179.78(17) ?
    C1 S1 C2 C3 . . . . 179.4(2) ?
    C1 S1 C2 C7 . . . . -0.03(16) ?
    C7 C2 C3 C4 . . . . -0.6(3) ?
    S1 C2 C3 C4 . . . . -179.92(18) ?
    C2 C3 C4 F1 . . . . 179.3(2) ?
    C2 C3 C4 C5 . . . . 0.3(4) ?
    F1 C4 C5 C6 . . . . -178.5(2) ?
    C3 C4 C5 C6 . . . . 0.6(4) ?
    C4 C5 C6 C7 . . . . -1.1(4) ?
    C1 N1 C7 C2 . . . . -0.5(3) ?
    C1 N1 C7 C6 . . . . -179.6(2) ?
    C3 C2 C7 N1 . . . . -179.2(2) ?
    S1 C2 C7 N1 . . . . 0.3(2) ?
    C3 C2 C7 C6 . . . . 0.1(3) ?
    S1 C2 C7 C6 . . . . 179.51(18) ?
    C5 C6 C7 N1 . . . . 179.9(2) ?
    C5 C6 C7 C2 . . . . 0.8(4) ?
    C1 N2 C8 C9 . . . . -177.1(2) ?
    N2 C8 C9 C10 . . . . 4.0(4) ?
    N2 C8 C9 C12 . . . . 176.8(2) ?
    C11 O1 C10 O3 . . . . -154.73(19) ?
    C11 O1 C10 C9 . . . . 28.7(3) ?
    C8 C9 C10 O3 . . . . -1.5(3) ?
    C12 C9 C10 O3 . . . . -174.1(2) ?
    C8 C9 C10 O1 . . . . 174.85(19) ?
    C12 C9 C10 O1 . . . . 2.3(3) ?
    C12 O2 C11 O1 . . . . 44.0(2) ?
    C12 O2 C11 C13 . . . . 159.25(18) ?
    C12 O2 C11 C14 . . . . -77.4(2) ?
    C10 O1 C11 O2 . . . . -50.9(2) ?
    C10 O1 C11 C13 . . . . -165.50(18) ?
    C10 O1 C11 C14 . . . . 70.9(2) ?
    C11 O2 C12 O4 . . . . 166.97(19) ?
    C11 O2 C12 C9 . . . . -15.7(3) ?
    C8 C9 C12 O4 . . . . -4.8(3) ?
    C10 C9 C12 O4 . . . . 168.2(2) ?
    C8 C9 C12 O2 . . . . 178.11(18) ?
    C10 C9 C12 O2 . . . . -9.0(3) ?
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
    N2 H2N O3 . 0.89(2) 2.19(2) 2.801(2) 125.5(19)
    N2 H2N O3 3_655 0.89(2) 2.23(2) 3.045(2) 151(2)
    C3 H3 O4 2_745 0.94(3) 2.58(3) 3.394(3) 145(2)
    C5 H5 F1 3_956 0.90(3) 2.46(3) 3.356(3) 174(2)
data_global
_journal_date_recd_electronic     2006-01-12
_journal_date_accepted     2006-01-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      2
_journal_page_first     o742
_journal_page_last     o743
_journal_paper_category     EO
_journal_coeditor_code     TK6307
_publ_contact_author
;
Sabine Foro
;
_publ_contact_author_email     foro@tu-darmstadt.de
_publ_contact_author_fax     '06151/ 166023'
_publ_contact_author_phone     '06151/ 164363'
_publ_section_title
;
5-[(6-Fluoro-1,3-benzothiazol-2-ylamino)methylene]-2,2-dimethyl-1,3-dioxane-
4,6-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'da Silva, Luiz Everson'
;
Departamento de Química--UFSC
88040-900 Florianópolis
SC
Brazil
and
Clemens Schöpf-Institut für Organische Chemie und Biochemie
Technische Universität Darmstadt
Petersenstraße 22
D-64287 Darmstadt
Germany
;
    'Joussef, Antonio Carlos'
;
Departamento de Química--UFSC
88040-900 Florianópolis
SC
Brazil
;
    'Foro, Sabine'
;
Clemens Schöpf-Institut für Organische Chemie und Biochemie
Technische Universität Darmstadt
Petersenstraße 22
D-64287 Darmstadt
Germany
;
    'Schmidt, Boris'
;
Clemens Schöpf-Institut für Organische Chemie und Biochemie
Technische Universität Darmstadt
Petersenstraße 22
D-64287 Darmstadt
Germany
;
