# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ajt1m
_database_code_depnum_ccdc_archive 'CCDC 1412289'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 F3 N2 O2'
_chemical_formula_weight         244.18

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   P21

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

_cell_length_a                   8.085(5)
_cell_length_b                   6.710(4)
_cell_length_c                   10.341(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.418(9)
_cell_angle_gamma                90.00
_cell_volume                     560.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1142
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.30

_exptl_crystal_description       PLATES
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'BRUKER SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3502
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0783
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         24.00
_reflns_number_total             1733
_reflns_number_gt                1304
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_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)+(0.0792P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         1733
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0902
_refine_ls_wR_factor_ref         0.1827
_refine_ls_wR_factor_gt          0.1719
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_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 0.0360(5) 0.8500(7) 0.8206(5) 0.0854(14) Uani 1 1 d . . .
F2 F 0.0645(5) 0.6436(8) 0.9742(4) 0.0975(16) Uani 1 1 d . . .
F3 F -0.0352(5) 0.5488(8) 0.7884(5) 0.1105(19) Uani 1 1 d . . .
O1 O 0.6224(7) 0.8864(9) 0.8515(5) 0.0866(17) Uani 1 1 d . . .
O2 O 0.5946(6) 0.5716(9) 0.8222(6) 0.102(2) Uani 1 1 d . . .
N1 N 0.2978(9) 0.2400(8) 0.8600(5) 0.082(2) Uani 1 1 d . . .
N2 N 0.5440(7) 0.7308(9) 0.8503(4) 0.0515(13) Uani 1 1 d . . .
C1 C 0.2232(9) 0.4999(11) 0.5724(6) 0.0656(19) Uani 1 1 d . . .
H1A H 0.1985 0.3726 0.6011 0.079 Uiso 1 1 calc R . .
C2 C 0.2252(10) 0.5396(14) 0.4430(7) 0.086(3) Uani 1 1 d . . .
H2 H 0.1956 0.4380 0.3850 0.103 Uiso 1 1 calc R . .
C3 C 0.2678(11) 0.7183(15) 0.3943(6) 0.092(3) Uani 1 1 d . . .
H3 H 0.2729 0.7386 0.3057 0.110 Uiso 1 1 calc R . .
C4 C 0.3036(11) 0.8698(13) 0.4828(7) 0.085(3) Uani 1 1 d . . .
H4 H 0.3309 0.9959 0.4534 0.102 Uiso 1 1 calc R . .
C5 C 0.2991(9) 0.8358(10) 0.6122(6) 0.0614(19) Uani 1 1 d . . .
H5 H 0.3241 0.9392 0.6700 0.074 Uiso 1 1 calc R . .
C6 C 0.2583(7) 0.6510(8) 0.6597(5) 0.0390(13) Uani 1 1 d . . .
C7 C 0.2504(6) 0.6155(7) 0.8073(5) 0.0371(14) Uani 1 1 d . . .
C8 C 0.0741(8) 0.6666(11) 0.8467(7) 0.0594(18) Uani 1 1 d . . .
C9 C 0.2792(8) 0.4012(9) 0.8371(6) 0.0486(17) Uani 1 1 d . . .
C10 C 0.3719(7) 0.7443(8) 0.8913(6) 0.0420(14) Uani 1 1 d . . .
H10A H 0.3359 0.8822 0.8863 0.050 Uiso 1 1 calc R . .
H10B H 0.3695 0.7020 0.9809 0.050 Uiso 1 1 calc 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
F1 0.067(3) 0.086(3) 0.105(3) 0.001(3) 0.013(2) 0.044(2)
F2 0.082(3) 0.128(4) 0.086(3) 0.005(3) 0.040(2) 0.008(3)
F3 0.046(2) 0.137(5) 0.150(5) -0.028(3) 0.013(3) -0.030(3)
O1 0.065(4) 0.117(4) 0.077(4) 0.017(3) -0.008(3) -0.035(3)
O2 0.052(3) 0.113(5) 0.139(5) -0.073(4) 0.002(3) 0.017(3)
N1 0.135(6) 0.040(3) 0.069(4) 0.004(3) -0.007(4) -0.010(3)
N2 0.041(4) 0.076(4) 0.036(3) -0.013(3) -0.009(2) -0.011(3)
C1 0.082(5) 0.060(4) 0.054(5) -0.008(4) 0.000(4) 0.005(4)
C2 0.111(7) 0.123(7) 0.021(4) 0.000(5) -0.016(4) 0.007(6)
C3 0.121(7) 0.141(8) 0.012(4) 0.038(5) 0.003(4) 0.031(6)
C4 0.122(7) 0.099(6) 0.034(5) 0.027(4) -0.006(5) -0.001(5)
C5 0.089(5) 0.057(4) 0.038(4) -0.008(3) 0.003(4) -0.005(4)
C6 0.044(3) 0.046(3) 0.027(3) -0.003(3) -0.001(2) 0.017(3)
C7 0.028(3) 0.033(3) 0.049(4) -0.005(3) 0.002(3) 0.002(2)
C8 0.050(5) 0.063(4) 0.066(5) 0.000(4) 0.008(4) -0.003(4)
C9 0.068(5) 0.023(3) 0.056(4) -0.012(3) 0.004(3) -0.007(3)
C10 0.039(4) 0.038(3) 0.049(3) -0.013(3) 0.001(3) 0.013(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
F1 C8 1.293(8) . ?
F2 C8 1.334(7) . ?
F3 C8 1.306(7) . ?
O1 N2 1.221(7) . ?
O2 N2 1.186(6) . ?
N1 C9 1.116(7) . ?
N2 C10 1.482(7) . ?
C1 C2 1.366(9) . ?
C1 C6 1.376(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.353(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.550(8) . ?
C7 C9 1.486(8) . ?
C7 C10 1.538(7) . ?
C7 C8 1.544(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
O2 N2 O1 125.9(6) . . ?
O2 N2 C10 118.0(5) . . ?
O1 N2 C10 116.2(6) . . ?
C2 C1 C6 119.0(7) . . ?
C2 C1 H1A 120.5 . . ?
C6 C1 H1A 120.5 . . ?
C3 C2 C1 123.7(8) . . ?
C3 C2 H2 118.1 . . ?
C1 C2 H2 118.1 . . ?
C2 C3 C4 116.9(6) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 120.6(7) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.4(7) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.2(5) . . ?
C1 C6 C7 120.9(5) . . ?
C5 C6 C7 120.9(5) . . ?
C9 C7 C10 109.9(5) . . ?
C9 C7 C8 107.2(5) . . ?
C10 C7 C8 107.1(4) . . ?
C9 C7 C6 109.8(4) . . ?
C10 C7 C6 114.0(5) . . ?
C8 C7 C6 108.6(4) . . ?
F1 C8 F3 109.5(6) . . ?
F1 C8 F2 106.8(6) . . ?
F3 C8 F2 108.0(6) . . ?
F1 C8 C7 111.6(5) . . ?
F3 C8 C7 110.7(5) . . ?
F2 C8 C7 110.1(5) . . ?
N1 C9 C7 178.7(7) . . ?
N2 C10 C7 112.6(4) . . ?
N2 C10 H10A 109.1 . . ?
C7 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C7 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.054
