# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_100k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Betainium Chlorodifluoroacetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C7H12C1F2NO4
_chemical_formula_sum            'C7 H12 Cl F2 N O4'
_chemical_formula_weight         247.63

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'
Cl Cl 0.1484 0.1585 '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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   5.8555(5)
_cell_length_b                   7.4803(6)
_cell_length_c                   24.756(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.081(8)
_cell_angle_gamma                90.00
_cell_volume                     1076.06(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2679
_cell_measurement_theta_min      3.5040
_cell_measurement_theta_max      25.1680

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11375
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1885
_reflns_number_gt                1461
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0360P)²+0.8754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1885
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.3114(3) 0.2025(3) 0.23026(8) 0.0245(5) Uani 1 1 d . . .
O1 O -0.0647(3) 0.1984(3) 0.23889(8) 0.0275(6) Uani 1 1 d . . .
N1 N 0.4235(4) 0.1960(3) 0.34738(10) 0.0203(6) Uani 1 1 d . . .
C1 C 0.1556(5) 0.1966(4) 0.25785(13) 0.0200(7) Uani 1 1 d . . .
C2 C 0.1809(5) 0.1869(4) 0.31959(12) 0.0206(7) Uani 1 1 d . . .
H2A H 0.0923 0.2865 0.3332 0.025 Uiso 1 1 calc R . .
H2B H 0.1108 0.0738 0.3302 0.025 Uiso 1 1 calc R . .
C5 C 0.5648(5) 0.0409(4) 0.33120(13) 0.0253(7) Uani 1 1 d . . .
H5A H 0.4844 -0.0713 0.3367 0.038 Uiso 1 1 calc R . .
H5C H 0.7149 0.0409 0.3536 0.038 Uiso 1 1 calc R . .
H5B H 0.5869 0.0524 0.2928 0.038 Uiso 1 1 calc R . .
C4 C 0.4115(5) 0.1849(4) 0.40769(12) 0.0263(8) Uani 1 1 d . . .
H4A H 0.3177 0.2837 0.4188 0.039 Uiso 1 1 calc R . .
H4B H 0.5672 0.1931 0.4273 0.039 Uiso 1 1 calc R . .
H4C H 0.3419 0.0709 0.4162 0.039 Uiso 1 1 calc R . .
C3 C 0.5356(5) 0.3690(4) 0.33498(13) 0.0267(8) Uani 1 1 d . . .
H3A H 0.5592 0.3715 0.2965 0.040 Uiso 1 1 calc R . .
H3B H 0.6845 0.3795 0.3576 0.040 Uiso 1 1 calc R . .
H3C H 0.4364 0.4689 0.3427 0.040 Uiso 1 1 calc R . .
Cl1 Cl 0.33058(14) 0.19738(12) 0.04735(4) 0.0371(3) Uani 1 1 d . . .
F2 F -0.0912(3) 0.2048(3) 0.00861(7) 0.0370(5) Uani 1 1 d . . .
F1 F 0.0337(3) 0.4385(2) 0.05450(7) 0.0373(5) Uani 1 1 d . . .
O4 O -0.0385(3) 0.0093(3) 0.10665(8) 0.0279(5) Uani 1 1 d . . .
O3 O -0.1035(4) 0.2848(3) 0.13856(9) 0.0294(6) Uani 1 1 d . . .
C6 C -0.0411(5) 0.1742(4) 0.10518(12) 0.0212(7) Uani 1 1 d . . .
C7 C 0.0420(6) 0.2582(4) 0.05404(13) 0.0285(8) Uani 1 1 d . . .
H1 H -0.1107 0.2045 0.2022 0.034 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0241(11) 0.0230(13) 0.0271(12) -0.0010(9) 0.0056(10) -0.0025(9)
O1 0.0215(11) 0.0352(14) 0.0248(12) 0.0013(10) -0.0006(9) 0.0012(10)
N1 0.0199(13) 0.0154(14) 0.0254(14) -0.0014(11) 0.0022(11) -0.0019(11)
C1 0.0206(16) 0.0111(17) 0.0287(17) -0.0009(13) 0.0049(14) -0.0013(13)
C2 0.0179(15) 0.0159(17) 0.0282(17) -0.0018(13) 0.0042(13) 0.0003(13)
C5 0.0214(16) 0.0199(18) 0.0350(19) 0.0000(14) 0.0052(14) 0.0035(13)
C4 0.0282(17) 0.026(2) 0.0238(17) 0.0001(14) 0.0006(14) 0.0048(14)
C3 0.0260(17) 0.0172(18) 0.0369(19) 0.0001(15) 0.0035(15) -0.0060(14)
Cl1 0.0356(5) 0.0388(6) 0.0389(5) 0.0034(4) 0.0127(4) -0.0042(4)
F2 0.0460(12) 0.0358(12) 0.0265(11) 0.0011(9) -0.0067(9) -0.0050(9)
F1 0.0569(13) 0.0175(11) 0.0383(11) 0.0067(8) 0.0092(10) -0.0025(9)
O4 0.0319(13) 0.0156(13) 0.0366(13) 0.0024(10) 0.0055(10) -0.0020(10)
O3 0.0396(13) 0.0225(13) 0.0261(12) -0.0008(10) 0.0039(10) 0.0085(10)
C6 0.0166(15) 0.021(2) 0.0237(17) 0.0029(14) -0.0052(13) -0.0016(13)
C7 0.040(2) 0.020(2) 0.0237(17) -0.0023(14) -0.0010(15) -0.0023(14)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.206(3) . ?
O1 C1 1.317(3) . ?
O1 H1 0.9157 . ?
N1 C3 1.500(4) . ?
N1 C2 1.502(4) . ?
N1 C4 1.506(4) . ?
N1 C5 1.507(4) . ?
C1 C2 1.519(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5C 0.9800 . ?
C5 H5B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
Cl1 C7 1.777(4) . ?
F2 C7 1.348(4) . ?
F1 C7 1.350(4) . ?
O4 C6 1.234(4) . ?
O3 C6 1.255(4) . ?
C6 C7 1.545(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 120.6 . . ?
C3 N1 C2 111.0(2) . . ?
C3 N1 C4 109.0(2) . . ?
C2 N1 C4 107.1(2) . . ?
C3 N1 C5 109.9(2) . . ?
C2 N1 C5 111.3(2) . . ?
C4 N1 C5 108.4(2) . . ?
O2 C1 O1 125.0(3) . . ?
O2 C1 C2 125.8(3) . . ?
O1 C1 C2 109.2(2) . . ?
N1 C2 C1 115.3(2) . . ?
N1 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
N1 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5C C5 H5B 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O4 C6 O3 130.0(3) . . ?
O4 C6 C7 115.3(3) . . ?
O3 C6 C7 114.7(3) . . ?
F2 C7 F1 106.6(2) . . ?
F2 C7 C6 110.8(3) . . ?
F1 C7 C6 112.6(3) . . ?
F2 C7 Cl1 107.8(2) . . ?
F1 C7 Cl1 107.0(2) . . ?
C6 C7 Cl1 111.8(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 C1 61.0(3) . . . . ?
C4 N1 C2 C1 179.8(2) . . . . ?
C5 N1 C2 C1 -61.8(3) . . . . ?
O2 C1 C2 N1 3.5(4) . . . . ?
O1 C1 C2 N1 -176.2(2) . . . . ?
O4 C6 C7 F2 60.3(3) . . . . ?
O3 C6 C7 F2 -118.9(3) . . . . ?
O4 C6 C7 F1 179.5(2) . . . . ?
O3 C6 C7 F1 0.3(4) . . . . ?
O4 C6 C7 Cl1 -60.0(3) . . . . ?
O3 C6 C7 Cl1 120.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.068
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water/ethanol'
_database_code_depnum_ccdc_archive 'CCDC 1016861'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_150k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H12 Cl F2 N O4'
_chemical_formula_weight         247.63

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/m

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.8521(3)
_cell_length_b                   7.5170(4)
_cell_length_c                   12.7370(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.458(5)
_cell_angle_gamma                90.00
_cell_volume                     558.61(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1960
_cell_measurement_theta_min      3.4780
_cell_measurement_theta_max      28.4980

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.12197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3501
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1060
_reflns_number_gt                892
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+2.3925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1060
_refine_ls_number_parameters     90
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0874
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5061(3) 0.2500 0.09835(16) 0.0642(7) Uani 1 2 d S . .
C5 C 0.9147(9) 0.2500 0.2176(4) 0.0306(13) Uani 1 2 d S . .
F1 F 0.8982(9) 0.2500 0.0320(3) 0.118(3) Uani 1 2 d S . .
C6 C 0.8004(13) 0.2500 0.1097(6) 0.091(4) Uani 1 2 d S . .
O12 O 0.9534(8) 0.1080(7) 0.2549(4) 0.126(3) Uani 1 1 d . . .
O1 O 0.6589(6) 0.2500 0.4608(3) 0.0324(10) Uani 1 2 d S . .
N1 N 0.6588(7) 0.2500 0.6877(3) 0.0249(10) Uani 1 2 d S . .
C2 C 0.8752(9) 0.2500 0.6312(4) 0.0235(11) Uani 1 2 d S . .
H2A H 0.9664 0.1438 0.6536 0.028 Uiso 0.50 1 calc PR . .
H2B H 0.9664 0.3562 0.6536 0.028 Uiso 0.50 1 calc PR . .
O2 O 1.0413(7) 0.2500 0.4730(3) 0.0542(15) Uani 1 2 d S . .
C3 C 0.5190(7) 0.0864(6) 0.6621(3) 0.0359(10) Uani 1 1 d . . .
H3A H 0.3929 0.0800 0.7083 0.054 Uiso 1 1 calc R . .
H3B H 0.6163 -0.0192 0.6728 0.054 Uiso 1 1 calc R . .
H3C H 0.4566 0.0914 0.5885 0.054 Uiso 1 1 calc R . .
C4 C 0.7314(10) 0.2500 0.8044(4) 0.0346(14) Uani 1 2 d S . .
H4A H 0.8072 0.3629 0.8237 0.052 Uiso 0.50 1 calc PR . .
H4B H 0.8380 0.1515 0.8207 0.052 Uiso 0.50 1 calc PR . .
H4C H 0.5961 0.2357 0.8444 0.052 Uiso 0.50 1 calc PR . .
C1 C 0.8393(9) 0.2500 0.5120(4) 0.0275(12) Uani 1 2 d S . .
F2 F 0.8238(12) 0.0333(10) 0.0924(6) 0.092(3) Uani 0.50 1 d P . .
H4 H 1.0103 0.2500 0.4010 0.110 Uiso 1 2 d SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0416(10) 0.0869(16) 0.0606(12) 0.000 -0.0178(8) 0.000
C5 0.025(3) 0.044(4) 0.024(3) 0.000 0.008(2) 0.000
F1 0.078(4) 0.251(9) 0.025(2) 0.000 0.010(2) 0.000
C6 0.039(4) 0.207(14) 0.027(4) 0.000 0.002(3) 0.000
O12 0.087(3) 0.135(4) 0.166(5) 0.124(4) 0.079(3) 0.075(3)
O1 0.030(2) 0.040(2) 0.0250(19) 0.000 -0.0065(17) 0.000
N1 0.026(2) 0.027(3) 0.022(2) 0.000 0.0024(18) 0.000
C2 0.021(3) 0.029(3) 0.020(3) 0.000 -0.002(2) 0.000
O2 0.029(2) 0.110(5) 0.024(2) 0.000 0.0036(17) 0.000
C3 0.034(2) 0.036(3) 0.038(2) -0.002(2) 0.0037(17) -0.0123(19)
C4 0.038(3) 0.049(4) 0.016(3) 0.000 0.001(2) 0.000
C1 0.027(3) 0.030(3) 0.026(3) 0.000 0.000(2) 0.000
F2 0.097(5) 0.077(5) 0.096(5) -0.066(5) -0.038(4) 0.036(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.717(8) . ?
C5 O12 1.183(5) 4_565 ?
C5 O12 1.183(5) . ?
C5 C6 1.481(9) . ?
F1 C6 1.181(8) . ?
C6 F2 1.651(7) 4_565 ?
C6 F2 1.651(7) . ?
O1 C1 1.198(6) . ?
N1 C3 1.499(5) . ?
N1 C3 1.499(5) 4_565 ?
N1 C2 1.504(6) . ?
N1 C4 1.514(6) . ?
C2 C1 1.516(7) . ?
O2 C1 1.317(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 C5 O12 128.9(9) 4_565 . ?
O12 C5 C6 115.6(4) 4_565 . ?
O12 C5 C6 115.6(4) . . ?
F1 C6 C5 124.4(7) . . ?
F1 C6 F2 80.6(4) . 4_565 ?
C5 C6 F2 95.0(4) . 4_565 ?
F1 C6 F2 80.6(4) . . ?
C5 C6 F2 95.0(4) . . ?
F2 C6 F2 161.3(9) 4_565 . ?
F1 C6 Cl1 118.5(6) . . ?
C5 C6 Cl1 117.1(5) . . ?
F2 C6 Cl1 94.7(4) 4_565 . ?
F2 C6 Cl1 94.7(4) . . ?
C3 N1 C3 110.3(4) . 4_565 ?
C3 N1 C2 111.2(3) . . ?
C3 N1 C2 111.2(3) 4_565 . ?
C3 N1 C4 108.7(3) . . ?
C3 N1 C4 108.7(3) 4_565 . ?
C2 N1 C4 106.7(4) . . ?
N1 C2 C1 115.0(4) . . ?
O1 C1 O2 125.0(5) . . ?
O1 C1 C2 126.4(5) . . ?
O2 C1 C2 108.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 1016862'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_200k

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H12 Cl F2 N O4'
_chemical_formula_weight         247.63

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/m

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.8745(3)
_cell_length_b                   7.5347(3)
_cell_length_c                   12.7728(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.896(4)
_cell_angle_gamma                90.00
_cell_volume                     563.29(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1259
_cell_measurement_theta_min      3.7060
_cell_measurement_theta_max      26.8710

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2557
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1070
_reflns_number_gt                862
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0405P)²+1.8535P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1070
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.1864
_refine_ls_wR_factor_gt          0.1755
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5053(4) 0.2500 0.59763(18) 0.0846(8) Uani 1 2 d S . .
C5 C 0.9110(10) 0.2500 0.7183(4) 0.0386(14) Uani 1 2 d S . .
F2 F 0.8968(11) 0.2500 0.5342(4) 0.154(4) Uani 1 2 d S . .
C6 C 0.7976(14) 0.2500 0.6095(6) 0.092(4) Uani 1 2 d S . .
F1 F 0.8213(14) 0.0386(11) 0.5910(7) 0.119(4) Uani 0.50 1 d P . .
O2 O 0.6575(7) 0.2500 0.9615(3) 0.0411(10) Uani 1 2 d S . .
N1 N 0.6622(7) 0.2500 1.1875(3) 0.0312(10) Uani 1 2 d S . .
C2 C 0.8752(9) 0.2500 1.1312(4) 0.0295(12) Uani 1 2 d S . .
H2A H 0.9665 0.1441 1.1535 0.035 Uiso 0.50 1 calc PR . .
H2B H 0.9665 0.3559 1.1535 0.035 Uiso 0.50 1 calc PR . .
O1 O 1.0382(7) 0.2500 0.9732(3) 0.0659(16) Uani 1 2 d S . .
C4 C 0.7370(11) 0.2500 1.3039(4) 0.0446(15) Uani 1 2 d S . .
C1 C 0.8382(10) 0.2500 1.0121(4) 0.0349(13) Uani 1 2 d S . .
C3 C 0.5222(7) 0.0869(6) 1.1624(3) 0.0465(11) Uani 1 1 d . . .
H3A H 0.4583 0.0916 1.0890 0.070 Uiso 1 1 calc R . .
H3B H 0.3977 0.0809 1.2086 0.070 Uiso 1 1 calc R . .
H3C H 0.6192 -0.0185 1.1731 0.070 Uiso 1 1 calc R . .
O3 O 0.9483(8) 0.1080(7) 0.7559(4) 0.132(2) Uani 1 1 d . . .
H1 H 1.0204 0.2500 0.9003 0.158 Uiso 1 2 d SR . .
H4A H 0.6007 0.2500 1.3383 0.042(16) Uiso 1 2 d SR . .
H4B H 0.8253 0.1370 1.3132 0.065(15) Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0579(12) 0.1127(19) 0.0781(14) 0.000 -0.0247(10) 0.000
C5 0.034(3) 0.051(4) 0.031(3) 0.000 0.008(2) 0.000
F2 0.107(5) 0.323(13) 0.033(3) 0.000 0.016(3) 0.000
C6 0.053(5) 0.188(12) 0.034(4) 0.000 0.001(3) 0.000
F1 0.131(7) 0.101(6) 0.115(6) -0.087(5) -0.047(5) 0.046(5)
O2 0.039(2) 0.054(3) 0.0286(19) 0.000 -0.0078(17) 0.000
N1 0.033(2) 0.033(2) 0.027(2) 0.000 0.0016(18) 0.000
C2 0.030(3) 0.033(3) 0.025(3) 0.000 -0.003(2) 0.000
O1 0.039(2) 0.129(5) 0.030(2) 0.000 0.0053(18) 0.000
C4 0.049(4) 0.060(4) 0.024(3) 0.000 0.004(2) 0.000
C1 0.038(3) 0.036(3) 0.030(3) 0.000 0.001(2) 0.000
C3 0.044(2) 0.046(3) 0.050(2) 0.001(2) 0.0035(19) -0.014(2)
O3 0.103(3) 0.141(4) 0.162(5) 0.120(4) 0.074(3) 0.077(3)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.711(8) . ?
C5 O3 1.185(5) 4_565 ?
C5 O3 1.185(5) . ?
C5 C6 1.489(9) . ?
F2 C6 1.166(9) . ?
C6 F1 1.618(8) . ?
C6 F1 1.618(8) 4_565 ?
O2 C1 1.195(6) . ?
N1 C2 1.496(6) . ?
N1 C3 1.498(5) . ?
N1 C3 1.498(5) 4_565 ?
N1 C4 1.513(7) . ?
C2 C1 1.518(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O1 C1 1.314(7) . ?
O1 H1 0.9283 . ?
C4 H4A 0.9458 . ?
C4 H4B 0.9992 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C5 O3 129.0(8) 4_565 . ?
O3 C5 C6 115.5(4) 4_565 . ?
O3 C5 C6 115.5(4) . . ?
F2 C6 C5 123.7(7) . . ?
F2 C6 F1 79.9(5) . . ?
C5 C6 F1 95.7(4) . . ?
F2 C6 F1 79.9(5) . 4_565 ?
C5 C6 F1 95.7(4) . 4_565 ?
F1 C6 F1 159.8(10) . 4_565 ?
F2 C6 Cl1 119.7(6) . . ?
C5 C6 Cl1 116.6(5) . . ?
F1 C6 Cl1 94.9(4) . . ?
F1 C6 Cl1 94.9(4) 4_565 . ?
C2 N1 C3 111.3(3) . . ?
C2 N1 C3 111.3(3) . 4_565 ?
C3 N1 C3 110.2(4) . 4_565 ?
C2 N1 C4 106.7(4) . . ?
C3 N1 C4 108.6(3) . . ?
C3 N1 C4 108.6(3) 4_565 . ?
N1 C2 C1 115.3(4) . . ?
N1 C2 H2A 108.4 . . ?
C1 C2 H2A 108.4 . . ?
N1 C2 H2B 108.4 . . ?
C1 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C1 O1 H1 110.6 . . ?
N1 C4 H4A 105.7 . . ?
N1 C4 H4B 102.8 . . ?
H4A C4 H4B 113.3 . . ?
O2 C1 O1 125.3(5) . . ?
O2 C1 C2 125.9(5) . . ?
O1 C1 C2 108.8(5) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C5 C6 F2 90.5(5) 4_565 . . . ?
O3 C5 C6 F2 -90.5(5) . . . . ?
O3 C5 C6 F1 172.2(6) 4_565 . . . ?
O3 C5 C6 F1 -8.9(8) . . . . ?
O3 C5 C6 F1 8.9(8) 4_565 . . 4_565 ?
O3 C5 C6 F1 -172.2(6) . . . 4_565 ?
O3 C5 C6 Cl1 -89.5(5) 4_565 . . . ?
O3 C5 C6 Cl1 89.5(5) . . . . ?
C3 N1 C2 C1 61.7(3) . . . . ?
C3 N1 C2 C1 -61.7(3) 4_565 . . . ?
C4 N1 C2 C1 180.000(3) . . . . ?
N1 C2 C1 O2 0.000(4) . . . . ?
N1 C2 C1 O1 180.000(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 1016863'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_230K

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H12 Cl F2 N O4'
_chemical_formula_weight         247.63

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/m

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.8905(3)
_cell_length_b                   7.5414(5)
_cell_length_c                   12.7949(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.151(5)
_cell_angle_gamma                90.00
_cell_volume                     566.09(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    1597
_cell_measurement_theta_min      3.9360
_cell_measurement_theta_max      27.7150

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3402
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1076
_reflns_number_gt                851
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0366P)²+1.7926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1076
_refine_ls_number_parameters     90
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0862
_refine_ls_wR_factor_ref         0.1799
_refine_ls_wR_factor_gt          0.1699
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.4941(4) 0.2500 0.90253(18) 0.0955(9) Uani 1 2 d S . .
C5 C 0.0903(9) 0.2500 0.7810(4) 0.0429(14) Uani 1 2 d S . .
O3 O 0.0540(8) 0.1083(7) 0.7436(4) 0.136(2) Uani 1 1 d . . .
C6 C 0.2027(14) 0.2500 0.8902(6) 0.095(3) Uani 1 2 d S . .
F1 F 0.1039(11) 0.2500 0.9648(4) 0.171(4) Uani 1 2 d S . .
O2 O 0.3431(6) 0.2500 0.5382(3) 0.0446(10) Uani 1 2 d S . .
N1 N 0.3361(7) 0.2500 0.3127(3) 0.0338(10) Uani 1 2 d S . .
C2 C 0.1248(8) 0.2500 0.3693(4) 0.0318(11) Uani 1 2 d S . .
H2A H 0.0335 0.1442 0.3471 0.038 Uiso 0.50 1 calc PR . .
H2B H 0.0335 0.3558 0.3471 0.038 Uiso 0.50 1 calc PR . .
C1 C 0.1620(9) 0.2500 0.4877(4) 0.0369(12) Uani 1 2 d S . .
O1 O -0.0369(7) 0.2500 0.5267(3) 0.0696(16) Uani 1 2 d S . .
C4 C 0.2609(10) 0.2500 0.1968(4) 0.0484(15) Uani 1 2 d S . .
H4A H 0.1685 0.3557 0.1793 0.073 Uiso 0.50 1 calc PR . .
H4B H 0.1701 0.1435 0.1791 0.073 Uiso 0.50 1 calc PR . .
H4C H 0.3952 0.2507 0.1568 0.073 Uiso 1 2 calc SR . .
C3 C 0.4751(7) 0.0869(6) 0.3377(3) 0.0503(11) Uani 1 1 d . . .
H3A H 0.6011 0.0820 0.2928 0.076 Uiso 1 1 calc R . .
H3B H 0.3787 -0.0183 0.3254 0.076 Uiso 1 1 calc R . .
H3C H 0.5364 0.0901 0.4115 0.076 Uiso 1 1 calc R . .
F2 F 0.1796(14) 0.0412(11) 0.9095(7) 0.130(4) Uani 0.50 1 d P . .
H1 H -0.0364 0.2500 0.5982 0.156 Uiso 1 2 d SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0651(13) 0.126(2) 0.0894(16) 0.000 -0.0261(11) 0.000
C5 0.035(3) 0.057(4) 0.038(3) 0.000 0.007(2) 0.000
O3 0.107(3) 0.150(4) 0.161(4) -0.119(4) 0.073(3) -0.078(3)
C6 0.063(5) 0.184(11) 0.037(4) 0.000 0.003(3) 0.000
F1 0.124(5) 0.356(14) 0.036(3) 0.000 0.021(3) 0.000
O2 0.042(2) 0.058(3) 0.0316(19) 0.000 -0.0076(16) 0.000
N1 0.033(2) 0.038(2) 0.030(2) 0.000 0.0019(17) 0.000
C2 0.031(3) 0.035(3) 0.029(3) 0.000 -0.002(2) 0.000
C1 0.039(3) 0.038(3) 0.033(3) 0.000 0.000(2) 0.000
O1 0.040(2) 0.134(5) 0.035(2) 0.000 0.0069(18) 0.000
C4 0.050(3) 0.068(4) 0.027(3) 0.000 0.003(2) 0.000
C3 0.048(2) 0.049(3) 0.054(2) -0.001(2) 0.0040(19) 0.016(2)
F2 0.144(7) 0.115(6) 0.121(6) 0.093(6) -0.045(5) -0.048(5)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.709(8) . ?
C5 O3 1.183(5) . ?
C5 O3 1.183(5) 4_565 ?
C5 C6 1.491(9) . ?
C6 F1 1.162(9) . ?
C6 F2 1.602(8) . ?
C6 F2 1.602(8) 4_565 ?
O2 C1 1.197(6) . ?
N1 C2 1.496(6) . ?
N1 C3 1.496(4) 4_565 ?
N1 C3 1.496(4) . ?
N1 C4 1.508(6) . ?
C2 C1 1.511(7) . ?
C1 O1 1.314(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C5 O3 129.3(8) . 4_565 ?
O3 C5 C6 115.4(4) . . ?
O3 C5 C6 115.4(4) 4_565 . ?
F1 C6 C5 123.8(7) . . ?
F1 C6 F2 79.5(5) . . ?
C5 C6 F2 96.2(4) . . ?
F1 C6 F2 79.5(5) . 4_565 ?
C5 C6 F2 96.2(4) . 4_565 ?
F2 C6 F2 158.9(10) . 4_565 ?
F1 C6 Cl1 119.8(6) . . ?
C5 C6 Cl1 116.4(5) . . ?
F2 C6 Cl1 94.8(4) . . ?
F2 C6 Cl1 94.8(4) 4_565 . ?
C2 N1 C3 111.0(3) . 4_565 ?
C2 N1 C3 111.0(3) . . ?
C3 N1 C3 110.6(4) 4_565 . ?
C2 N1 C4 107.0(4) . . ?
C3 N1 C4 108.5(3) 4_565 . ?
C3 N1 C4 108.5(3) . . ?
N1 C2 C1 115.7(4) . . ?
O2 C1 O1 125.2(5) . . ?
O2 C1 C2 125.7(5) . . ?
O1 C1 C2 109.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 1016864'
