data_global
_audit_creation_method                  'APEX2 v2010.13-1'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_I
_chemical_name_systematic               ?
_chemical_name_common                   JDA011
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C8 H3 Cl F5 N O'
_chemical_formula_iupac                 ?
_chemical_formula_weight                259.56

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 1 21/c 1'
_space_group_name_Hall                  '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'

_cell_length_a                          4.6880(11)
_cell_length_b                          15.110(4)
_cell_length_c                          12.828(3)
_cell_angle_alpha                       90
_cell_angle_beta                        97.727(3)
_cell_angle_gamma                       90
_cell_volume                            900.4(4)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           5121
_cell_measurement_theta_min             2.6959
_cell_measurement_theta_max             27.2653
_cell_measurement_temperature           100.(2)

_exptl_crystal_description              needle
_exptl_crystal_colour                   'clear colourless'
_exptl_crystal_size_max                 0.980
_exptl_crystal_size_mid                 0.040
_exptl_crystal_size_min                 0.020
_exptl_crystal_density_diffrn           1.915
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    512

_exptl_absorpt_coefficient_mu           0.480
_exptl_absorpt_correction_type          numerical
_exptl_absorpt_process_details          'Sadabs Version 2008/1'
_exptl_absorpt_correction_T_min         0.73
_exptl_absorpt_correction_T_max         0.99

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             100.(2)

_diffrn_source                          'fine-focus tube'
_diffrn_source_type                     ?

_diffrn_radiation_type                  Mo
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         graphite

_diffrn_measurement_device_type         'Bruker APEX II CCD'
_diffrn_measurement_method              'omega scans'

_diffrn_detector_area_resol_mean        8.3333

_diffrn_reflns_number                   9795
_diffrn_reflns_av_R_equivalents         0.0381
_diffrn_reflns_av_sigmaI/netI           0.0249
_diffrn_reflns_theta_min                2.09
_diffrn_reflns_theta_max                25.35
_diffrn_reflns_theta_full               25.35
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full    1.000
_diffrn_reflns_limit_h_min              -5
_diffrn_reflns_limit_h_max              5
_diffrn_reflns_limit_k_min              -18
_diffrn_reflns_limit_k_max              18
_diffrn_reflns_limit_l_min              -15
_diffrn_reflns_limit_l_max              15

_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                    1653
_reflns_number_gt                       1408
_reflns_threshold_expression            >2sigma(I)

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0358
_refine_ls_R_factor_gt                  0.0273
_refine_ls_wR_factor_gt                 0.0614
_refine_ls_wR_factor_ref                0.0654
_refine_ls_goodness_of_fit_ref          1.023
_refine_ls_restrained_S_all             1.023
_refine_ls_number_reflns                1653
_refine_ls_number_parameters            149
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           refU
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
    'calc w=1/[σ²(Fo²)+(0.0242P)²+0.5952P] 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                 0.012
_refine_ls_shift/su_mean                0.002
_refine_diff_density_max                0.270
_refine_diff_density_min                -0.248
_refine_ls_extinction_method            SHELXL
_refine_ls_extinction_coef              0.0029(11)

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'
    Cl Cl 0.1484 0.1585
     'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              
    'Bruker Instrument Service v2010.13.0.0'
_computing_cell_refinement              'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction               'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_solution           'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement         'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics           'Bruker APEX2'
_computing_publication_material         'Bruker APEX2'

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 1.0795(4) 0.77114(12) 0.59491(14) 0.0214(4) Uani d . 1 . .
    F F1 1.2338(2) 0.74515(7) 0.68532(8) 0.0287(3) Uani d . 1 . .
    C C2 1.1552(4) 0.84939(12) 0.54987(15) 0.0234(4) Uani d . 1 . .
    F F2 1.3787(2) 0.89715(7) 0.59617(9) 0.0322(3) Uani d . 1 . .
    C C3 0.9999(4) 0.87870(12) 0.45748(15) 0.0245(4) Uani d . 1 . .
    F F3 1.0749(3) 0.95345(7) 0.41190(9) 0.0329(3) Uani d . 1 . .
    C C4 0.7663(4) 0.83054(13) 0.41176(14) 0.0236(4) Uani d . 1 . .
    F F4 0.6083(3) 0.86030(8) 0.32346(9) 0.0332(3) Uani d . 1 . .
    C C5 0.6940(4) 0.75245(12) 0.45679(14) 0.0206(4) Uani d . 1 . .
    F F5 0.4656(2) 0.70662(7) 0.41077(8) 0.0260(3) Uani d . 1 . .
    C C6 0.8502(4) 0.72033(12) 0.54867(14) 0.0199(4) Uani d . 1 . .
    N N1 0.7738(3) 0.63955(10) 0.59269(12) 0.0203(3) Uani d . 1 . .
    H H1 0.5979 0.6332 0.6084 0.031(6) Uiso calc R 1 . .
    C C7 0.9619(4) 0.57128(12) 0.61166(14) 0.0197(4) Uani d . 1 . .
    O O1 1.2119(3) 0.57515(8) 0.59417(10) 0.0241(3) Uani d . 1 . .
    C C8 0.8302(4) 0.48969(12) 0.65452(15) 0.0219(4) Uani d . 1 . .
    H H3 0.6947 0.4619 0.5981 0.032(6) Uiso calc R 1 . .
    H H2 0.7202 0.5071 0.7119 0.034(6) Uiso calc R 1 . .
    Cl Cl1 1.09884(10) 0.41217(3) 0.70292(4) 0.02792(15) 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 0.0204(9) 0.0230(10) 0.0208(10) 0.0052(8) 0.0021(8) -0.0019(8)
    F1 0.0272(6) 0.0291(6) 0.0268(6) 0.0030(5) -0.0071(5) -0.0005(5)
    C2 0.0185(9) 0.0224(10) 0.0292(10) -0.0023(8) 0.0029(8) -0.0072(8)
    F2 0.0245(6) 0.0286(6) 0.0420(7) -0.0077(5) -0.0006(5) -0.0068(5)
    C3 0.0279(10) 0.0182(9) 0.0291(10) -0.0024(8) 0.0102(8) -0.0002(8)
    F3 0.0411(7) 0.0236(6) 0.0356(7) -0.0065(5) 0.0104(5) 0.0037(5)
    C4 0.0265(10) 0.0256(10) 0.0184(9) 0.0021(8) 0.0024(8) 0.0008(8)
    F4 0.0407(7) 0.0325(7) 0.0242(6) -0.0021(5) -0.0040(5) 0.0061(5)
    C5 0.0173(9) 0.0232(10) 0.0212(9) -0.0004(8) 0.0021(7) -0.0045(8)
    F5 0.0211(6) 0.0273(6) 0.0280(6) -0.0038(5) -0.0020(4) -0.0019(5)
    C6 0.0186(9) 0.0194(9) 0.0226(10) 0.0020(7) 0.0060(7) -0.0005(7)
    N1 0.0159(8) 0.0213(8) 0.0249(8) 0.0003(6) 0.0068(6) 0.0029(6)
    C7 0.0190(9) 0.0225(10) 0.0173(9) 0.0004(7) 0.0012(7) -0.0026(7)
    O1 0.0149(7) 0.0254(7) 0.0327(8) 0.0003(5) 0.0059(5) 0.0019(6)
    C8 0.0178(9) 0.0220(10) 0.0261(10) 0.0021(8) 0.0034(7) 0.0012(8)
    Cl1 0.0227(3) 0.0250(3) 0.0364(3) 0.00404(19) 0.00498(19) 0.0066(2)

_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
    C1 F1 . 1.340(2) ?
    C1 C2 . 1.383(3) ?
    C1 C6 . 1.388(3) ?
    C2 F2 . 1.343(2) ?
    C2 C3 . 1.378(3) ?
    C3 F3 . 1.340(2) ?
    C3 C4 . 1.378(3) ?
    C4 F4 . 1.345(2) ?
    C4 C5 . 1.376(3) ?
    C5 F5 . 1.343(2) ?
    C5 C6 . 1.389(2) ?
    C6 N1 . 1.411(2) ?
    N1 C7 . 1.358(2) ?
    N1 H1 . 0.88 ?
    C7 O1 . 1.224(2) ?
    C7 C8 . 1.515(3) ?
    C8 Cl1 . 1.7700(18) ?
    C8 H3 . 0.99 ?
    C8 H2 . 0.99 ?

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
    F1 C1 C2 . . 118.23(16) ?
    F1 C1 C6 . . 120.30(16) ?
    C2 C1 C6 . . 121.47(17) ?
    F2 C2 C3 . . 119.88(17) ?
    F2 C2 C1 . . 120.22(17) ?
    C3 C2 C1 . . 119.90(17) ?
    F3 C3 C2 . . 120.44(17) ?
    F3 C3 C4 . . 119.96(17) ?
    C2 C3 C4 . . 119.60(17) ?
    F4 C4 C5 . . 120.08(17) ?
    F4 C4 C3 . . 119.87(17) ?
    C5 C4 C3 . . 120.05(17) ?
    F5 C5 C4 . . 118.98(16) ?
    F5 C5 C6 . . 119.41(16) ?
    C4 C5 C6 . . 121.60(17) ?
    C1 C6 C5 . . 117.34(17) ?
    C1 C6 N1 . . 122.10(16) ?
    C5 C6 N1 . . 120.56(16) ?
    C7 N1 C6 . . 122.36(15) ?
    C7 N1 H1 . . 118.8 ?
    C6 N1 H1 . . 118.8 ?
    O1 C7 N1 . . 123.07(17) ?
    O1 C7 C8 . . 123.54(16) ?
    N1 C7 C8 . . 113.39(15) ?
    C7 C8 Cl1 . . 111.13(13) ?
    C7 C8 H3 . . 109.4 ?
    Cl1 C8 H3 . . 109.4 ?
    C7 C8 H2 . . 109.4 ?
    Cl1 C8 H2 . . 109.4 ?
    H3 C8 H2 . . 108.0 ?

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
    F1 C1 C2 F2 . . . . 0.3(3) ?
    C6 C1 C2 F2 . . . . -179.81(16) ?
    F1 C1 C2 C3 . . . . -179.37(16) ?
    C6 C1 C2 C3 . . . . 0.5(3) ?
    F2 C2 C3 F3 . . . . 1.8(3) ?
    C1 C2 C3 F3 . . . . -178.58(16) ?
    F2 C2 C3 C4 . . . . -178.36(17) ?
    C1 C2 C3 C4 . . . . 1.3(3) ?
    F3 C3 C4 F4 . . . . -2.3(3) ?
    C2 C3 C4 F4 . . . . 177.83(17) ?
    F3 C3 C4 C5 . . . . 178.13(16) ?
    C2 C3 C4 C5 . . . . -1.8(3) ?
    F4 C4 C5 F5 . . . . 0.5(3) ?
    C3 C4 C5 F5 . . . . -179.95(16) ?
    F4 C4 C5 C6 . . . . -179.19(16) ?
    C3 C4 C5 C6 . . . . 0.4(3) ?
    F1 C1 C6 C5 . . . . 178.06(15) ?
    C2 C1 C6 C5 . . . . -1.8(3) ?
    F1 C1 C6 N1 . . . . -1.3(3) ?
    C2 C1 C6 N1 . . . . 178.81(16) ?
    F5 C5 C6 C1 . . . . -178.28(16) ?
    C4 C5 C6 C1 . . . . 1.4(3) ?
    F5 C5 C6 N1 . . . . 1.1(3) ?
    C4 C5 C6 N1 . . . . -179.26(17) ?
    C1 C6 N1 C7 . . . . -57.2(2) ?
    C5 C6 N1 C7 . . . . 123.47(19) ?
    C6 N1 C7 O1 . . . . 1.5(3) ?
    C6 N1 C7 C8 . . . . -177.41(15) ?
    O1 C7 C8 Cl1 . . . . 13.2(2) ?
    N1 C7 C8 Cl1 . . . . -167.83(13) ?

