# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_z

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H5 F3 N2 O4'
_chemical_formula_weight         286.17

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   11.2169(9)
_cell_length_b                   15.8678(13)
_cell_length_c                   6.8648(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.601(3)
_cell_angle_gamma                90.00
_cell_volume                     1164.65(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9533
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13493
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2054
_reflns_number_gt                1273
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0502P)²+0.8402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2054
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
F1 F 0.6519(2) 0.1304(2) 0.5404(6) 0.1789(18) Uani 1 1 d . . .
F2 F 0.5204(3) 0.13147(18) 0.7080(4) 0.1221(10) Uani 1 1 d . . .
F3 F 0.5428(2) 0.23807(15) 0.5422(4) 0.0986(8) Uani 1 1 d . . .
O1 O 0.1904(3) 0.02018(17) 0.4746(5) 0.0885(9) Uani 1 1 d . . .
O2 O 0.0333(3) -0.05139(18) 0.2923(6) 0.1257(13) Uani 1 1 d . . .
O3 O 0.2761(2) 0.21913(17) 0.5270(4) 0.0792(8) Uani 1 1 d . . .
O4 O 0.26993(19) 0.08618(13) 0.1181(3) 0.0605(6) Uani 1 1 d . . .
N1 N 0.0879(3) 0.01441(19) 0.3456(6) 0.0753(9) Uani 1 1 d . . .
N2 N 0.3672(3) 0.0493(2) 0.0583(5) 0.0772(9) Uani 1 1 d . . .
C1 C 0.0264(3) 0.0931(2) 0.2550(5) 0.0558(8) Uani 1 1 d . . .
C2 C -0.1011(4) 0.0923(3) 0.1574(6) 0.0781(12) Uani 1 1 d . . .
H2A H -0.1461 0.0422 0.1390 0.094 Uiso 1 1 calc R . .
C3 C -0.1597(4) 0.1676(4) 0.0879(6) 0.0870(13) Uani 1 1 d . . .
H3A H -0.2453 0.1684 0.0211 0.104 Uiso 1 1 calc R . .
C4 C -0.0939(4) 0.2407(3) 0.1162(6) 0.0792(12) Uani 1 1 d . . .
H4A H -0.1351 0.2911 0.0699 0.095 Uiso 1 1 calc R . .
C5 C 0.0325(3) 0.2413(2) 0.2118(5) 0.0589(9) Uani 1 1 d . . .
H5A H 0.0762 0.2919 0.2296 0.071 Uiso 1 1 calc R . .
C6 C 0.0958(3) 0.16670(18) 0.2826(4) 0.0463(7) Uani 1 1 d . . .
C7 C 0.2333(3) 0.17336(19) 0.3830(5) 0.0509(8) Uani 1 1 d . . .
C8 C 0.3198(3) 0.12817(17) 0.2941(5) 0.0465(7) Uani 1 1 d . . .
C9 C 0.4455(3) 0.12134(18) 0.3510(5) 0.0526(8) Uani 1 1 d . . .
C10 C 0.4682(3) 0.0713(2) 0.1972(6) 0.0735(11) Uani 1 1 d . . .
H10A H 0.5478 0.0557 0.1957 0.088 Uiso 1 1 calc R . .
C11 C 0.5401(3) 0.1550(3) 0.5334(7) 0.0772(11) Uani 1 1 d . . .

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
F1 0.0452(14) 0.203(3) 0.260(4) -0.121(3) 0.0030(18) 0.0174(17)
F2 0.129(2) 0.120(2) 0.0862(18) 0.0118(16) -0.0141(16) -0.0158(17)
F3 0.0965(17) 0.0766(16) 0.1172(19) -0.0277(13) 0.0240(14) -0.0265(13)
O1 0.089(2) 0.0727(17) 0.114(2) 0.0325(16) 0.0459(18) 0.0171(16)
O2 0.157(3) 0.0579(18) 0.189(4) -0.027(2) 0.092(3) -0.0345(19)
O3 0.0558(14) 0.0958(19) 0.0848(17) -0.0430(16) 0.0196(13) -0.0003(13)
O4 0.0565(13) 0.0642(14) 0.0650(14) -0.0184(11) 0.0250(11) -0.0038(11)
N1 0.089(2) 0.058(2) 0.099(3) -0.0057(18) 0.059(2) -0.0076(19)
N2 0.075(2) 0.081(2) 0.090(2) -0.0299(18) 0.0470(19) -0.0042(17)
C1 0.056(2) 0.059(2) 0.059(2) -0.0087(16) 0.0268(16) -0.0065(16)
C2 0.064(2) 0.105(3) 0.073(3) -0.027(2) 0.032(2) -0.030(2)
C3 0.047(2) 0.145(4) 0.063(3) -0.005(3) 0.0080(19) 0.003(3)
C4 0.061(2) 0.114(3) 0.068(2) 0.024(2) 0.026(2) 0.027(2)
C5 0.055(2) 0.066(2) 0.062(2) 0.0085(16) 0.0267(16) 0.0106(16)
C6 0.0440(16) 0.0542(18) 0.0445(16) -0.0028(14) 0.0193(13) 0.0025(14)
C7 0.0496(18) 0.0494(17) 0.0548(19) -0.0038(15) 0.0172(15) 0.0022(14)
C8 0.0474(17) 0.0419(15) 0.0523(17) -0.0045(14) 0.0181(14) -0.0023(13)
C9 0.0452(18) 0.0447(16) 0.071(2) -0.0053(15) 0.0217(16) -0.0008(14)
C10 0.059(2) 0.066(2) 0.110(3) -0.017(2) 0.047(2) -0.0051(18)
C11 0.051(2) 0.075(3) 0.103(3) -0.016(2) 0.019(2) 0.0016(18)

_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
F1 C11 1.300(4) . ?
F2 C11 1.336(5) . ?
F3 C11 1.320(4) . ?
O1 N1 1.224(4) . ?
O2 N1 1.210(4) . ?
O3 C7 1.204(3) . ?
O4 C8 1.345(3) . ?
O4 N2 1.405(3) . ?
N1 C1 1.470(4) . ?
N2 C10 1.289(4) . ?
C1 C2 1.384(5) . ?
C1 C6 1.385(4) . ?
C2 C3 1.378(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.358(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.491(4) . ?
C7 C8 1.479(4) . ?
C8 C9 1.348(4) . ?
C9 C10 1.405(4) . ?
C9 C11 1.475(5) . ?
C10 H10A 0.9300 . ?

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
C8 O4 N2 108.7(2) . . ?
O2 N1 O1 124.2(4) . . ?
O2 N1 C1 118.4(4) . . ?
O1 N1 C1 117.4(3) . . ?
C10 N2 O4 104.9(3) . . ?
C2 C1 C6 122.0(3) . . ?
C2 C1 N1 118.8(3) . . ?
C6 C1 N1 119.1(3) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 C7 125.7(3) . . ?
C5 C6 C7 116.7(3) . . ?
O3 C7 C8 118.9(3) . . ?
O3 C7 C6 121.5(3) . . ?
C8 C7 C6 119.4(3) . . ?
O4 C8 C9 109.6(3) . . ?
O4 C8 C7 117.7(2) . . ?
C9 C8 C7 132.7(3) . . ?
C8 C9 C10 103.8(3) . . ?
C8 C9 C11 129.7(3) . . ?
C10 C9 C11 126.5(3) . . ?
N2 C10 C9 113.0(3) . . ?
N2 C10 H10A 123.5 . . ?
C9 C10 H10A 123.5 . . ?
F1 C11 F3 106.8(3) . . ?
F1 C11 F2 107.6(4) . . ?
F3 C11 F2 104.2(3) . . ?
F1 C11 C9 111.2(3) . . ?
F3 C11 C9 113.6(3) . . ?
F2 C11 C9 112.9(3) . . ?

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
C8 O4 N2 C10 -0.6(4) . . . . ?
O2 N1 C1 C2 17.0(5) . . . . ?
O1 N1 C1 C2 -161.1(3) . . . . ?
O2 N1 C1 C6 -167.5(3) . . . . ?
O1 N1 C1 C6 14.3(4) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
N1 C1 C2 C3 174.7(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C2 C1 C6 C5 1.2(4) . . . . ?
N1 C1 C6 C5 -174.1(3) . . . . ?
C2 C1 C6 C7 -179.1(3) . . . . ?
N1 C1 C6 C7 5.6(5) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C1 C6 C7 O3 -123.7(4) . . . . ?
C5 C6 C7 O3 55.9(4) . . . . ?
C1 C6 C7 C8 61.3(4) . . . . ?
C5 C6 C7 C8 -119.0(3) . . . . ?
N2 O4 C8 C9 0.7(3) . . . . ?
N2 O4 C8 C7 178.9(3) . . . . ?
O3 C7 C8 O4 -171.6(3) . . . . ?
C6 C7 C8 O4 3.5(4) . . . . ?
O3 C7 C8 C9 6.1(5) . . . . ?
C6 C7 C8 C9 -178.8(3) . . . . ?
O4 C8 C9 C10 -0.5(4) . . . . ?
C7 C8 C9 C10 -178.4(3) . . . . ?
O4 C8 C9 C11 -178.8(3) . . . . ?
C7 C8 C9 C11 3.4(6) . . . . ?
O4 N2 C10 C9 0.3(4) . . . . ?
C8 C9 C10 N2 0.1(4) . . . . ?
C11 C9 C10 N2 178.4(4) . . . . ?
C8 C9 C11 F1 176.0(4) . . . . ?
C10 C9 C11 F1 -1.9(6) . . . . ?
C8 C9 C11 F3 -63.4(5) . . . . ?
C10 C9 C11 F3 118.7(4) . . . . ?
C8 C9 C11 F2 55.0(5) . . . . ?
C10 C9 C11 F2 -122.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1005152'
