# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 980776'
_audit_update_record             
;
2014-01-09 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H7 F5 N2'
_chemical_formula_weight         310.23

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   9.1606(9)
_cell_length_b                   9.1763(10)
_cell_length_c                   15.3777(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1292.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4747
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.3

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7128
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2276
_reflns_number_gt                2053
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0575P)²+0.2083P] 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     SHELXL
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_number_reflns         2276
_refine_ls_number_parameters     204
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.082
_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
C1 C 0.4281(4) 0.4561(4) -0.24636(17) 0.0768(9) Uani 1 1 d U . .
H1 H 0.4256 0.5027 -0.3001 0.092 Uiso 1 1 calc R . .
C2 C 0.3480(3) 0.3347(4) -0.22438(19) 0.0713(8) Uani 1 1 d U . .
H2 H 0.2831 0.2842 -0.2598 0.086 Uiso 1 1 calc R . .
C3 C 0.3839(3) 0.3023(3) -0.13780(16) 0.0579(6) Uani 1 1 d . . .
H3 H 0.3461 0.2260 -0.1050 0.069 Uiso 1 1 calc R . .
C4 C 0.4849(3) 0.4035(3) -0.10993(14) 0.0490(5) Uani 1 1 d . . .
C5 C 0.5531(2) 0.4193(2) -0.02656(14) 0.0443(5) Uani 1 1 d . . .
C6 C 0.6501(2) 0.5281(2) -0.00466(15) 0.0472(5) Uani 1 1 d . . .
C7 C 0.7247(3) 0.5523(2) 0.07670(17) 0.0537(6) Uani 1 1 d . . .
H7 H 0.7162 0.4969 0.1271 0.064 Uiso 1 1 calc R . .
C8 C 0.8087(3) 0.6704(3) 0.0652(2) 0.0663(7) Uani 1 1 d . . .
H8 H 0.8696 0.7136 0.1061 0.080 Uiso 1 1 calc R . .
C9 C 0.7860(3) 0.7169(3) -0.0226(2) 0.0713(8) Uani 1 1 d . . .
H9 H 0.8328 0.7967 -0.0474 0.086 Uiso 1 1 calc R . .
C10 C 0.5152(2) 0.3063(2) 0.03947(14) 0.0407(5) Uani 1 1 d . . .
C11 C 0.5581(2) 0.1612(3) 0.03044(15) 0.0468(5) Uani 1 1 d . . .
C12 C 0.5245(3) 0.0561(2) 0.09039(15) 0.0492(5) Uani 1 1 d . . .
C13 C 0.4414(3) 0.0926(3) 0.16174(15) 0.0518(6) Uani 1 1 d . . .
C14 C 0.3957(3) 0.2327(3) 0.17313(14) 0.0494(5) Uani 1 1 d . . .
C15 C 0.4340(2) 0.3380(2) 0.11309(14) 0.0429(5) Uani 1 1 d . . .
N1 N 0.5099(3) 0.4968(3) -0.17856(14) 0.0611(6) Uani 1 1 d D . .
N2 N 0.6922(3) 0.6351(2) -0.06430(15) 0.0606(6) Uani 1 1 d . . .
F1 F 0.63957(17) 0.12270(15) -0.03841(10) 0.0651(4) Uani 1 1 d . . .
F2 F 0.5735(2) -0.07984(16) 0.08075(12) 0.0750(5) Uani 1 1 d . . .
F3 F 0.4061(2) -0.01042(18) 0.21994(10) 0.0759(5) Uani 1 1 d . . .
F4 F 0.3137(2) 0.26842(19) 0.24178(10) 0.0763(5) Uani 1 1 d . . .
F5 F 0.38767(16) 0.47434(14) 0.12694(9) 0.0563(4) Uani 1 1 d . . .
H1A H 0.562(3) 0.574(2) -0.1751(18) 0.050(7) Uiso 1 1 d D . .


_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
C1 N1 1.338(4) . ?
C1 C2 1.376(5) . ?
C2 C3 1.403(4) . ?
C3 C4 1.379(3) . ?
C4 N1 1.379(3) . ?
C4 C5 1.434(3) . ?
C5 C6 1.378(3) . ?
C5 C10 1.492(3) . ?
C6 N2 1.398(3) . ?
C6 C7 1.442(3) . ?
C7 C8 1.341(4) . ?
C8 C9 1.431(4) . ?
C9 N2 1.309(4) . ?
C10 C15 1.385(3) . ?
C10 C11 1.395(3) . ?
C11 F1 1.343(3) . ?
C11 C12 1.369(3) . ?
C12 F2 1.334(2) . ?
C12 C13 1.377(3) . ?
C13 F3 1.341(3) . ?
C13 C14 1.363(3) . ?
C14 F4 1.336(3) . ?
C14 C15 1.382(3) . ?
C15 F5 1.339(2) . ?

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
N1 C1 C2 109.5(3) . . ?
C1 C2 C3 106.3(3) . . ?
C4 C3 C2 108.0(2) . . ?
N1 C4 C3 107.0(2) . . ?
N1 C4 C5 123.3(2) . . ?
C3 C4 C5 129.7(2) . . ?
C6 C5 C4 124.9(2) . . ?
C6 C5 C10 119.2(2) . . ?
C4 C5 C10 115.89(19) . . ?
C5 C6 N2 121.8(2) . . ?
C5 C6 C7 128.9(2) . . ?
N2 C6 C7 109.3(2) . . ?
C8 C7 C6 106.3(2) . . ?
C7 C8 C9 106.4(2) . . ?
N2 C9 C8 112.7(2) . . ?
C15 C10 C11 115.7(2) . . ?
C15 C10 C5 122.37(18) . . ?
C11 C10 C5 122.0(2) . . ?
F1 C11 C12 118.1(2) . . ?
F1 C11 C10 119.1(2) . . ?
C12 C11 C10 122.8(2) . . ?
F2 C12 C11 120.5(2) . . ?
F2 C12 C13 120.1(2) . . ?
C11 C12 C13 119.3(2) . . ?
F3 C13 C14 120.3(2) . . ?
F3 C13 C12 119.6(2) . . ?
C14 C13 C12 120.1(2) . . ?
F4 C14 C13 120.4(2) . . ?
F4 C14 C15 119.9(2) . . ?
C13 C14 C15 119.7(2) . . ?
F5 C15 C14 117.82(19) . . ?
F5 C15 C10 119.77(18) . . ?
C14 C15 C10 122.4(2) . . ?
C1 N1 C4 109.3(2) . . ?
C9 N2 C6 105.2(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
N1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 N1 0.2(3) . . . . ?
C2 C3 C4 C5 178.6(2) . . . . ?
N1 C4 C5 C6 0.3(4) . . . . ?
C3 C4 C5 C6 -177.8(2) . . . . ?
N1 C4 C5 C10 -178.9(2) . . . . ?
C3 C4 C5 C10 3.0(3) . . . . ?
C4 C5 C6 N2 -0.5(3) . . . . ?
C10 C5 C6 N2 178.6(2) . . . . ?
C4 C5 C6 C7 -179.5(2) . . . . ?
C10 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 179.0(2) . . . . ?
N2 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 N2 0.8(3) . . . . ?
C6 C5 C10 C15 68.8(3) . . . . ?
C4 C5 C10 C15 -112.0(2) . . . . ?
C6 C5 C10 C11 -111.9(2) . . . . ?
C4 C5 C10 C11 67.4(3) . . . . ?
C15 C10 C11 F1 -178.68(19) . . . . ?
C5 C10 C11 F1 2.0(3) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
C5 C10 C11 C12 179.9(2) . . . . ?
F1 C11 C12 F2 0.9(3) . . . . ?
C10 C11 C12 F2 -177.0(2) . . . . ?
F1 C11 C12 C13 179.8(2) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
F2 C12 C13 F3 -2.2(3) . . . . ?
C11 C12 C13 F3 178.9(2) . . . . ?
F2 C12 C13 C14 177.7(2) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
F3 C13 C14 F4 -0.8(4) . . . . ?
C12 C13 C14 F4 179.3(2) . . . . ?
F3 C13 C14 C15 179.4(2) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
F4 C14 C15 F5 0.6(3) . . . . ?
C13 C14 C15 F5 -179.6(2) . . . . ?
F4 C14 C15 C10 -178.1(2) . . . . ?
C13 C14 C15 C10 1.7(4) . . . . ?
C11 C10 C15 F5 -179.8(2) . . . . ?
C5 C10 C15 F5 -0.4(3) . . . . ?
C11 C10 C15 C14 -1.0(3) . . . . ?
C5 C10 C15 C14 178.3(2) . . . . ?
C2 C1 N1 C4 -0.4(3) . . . . ?
C3 C4 N1 C1 0.1(3) . . . . ?
C5 C4 N1 C1 -178.4(2) . . . . ?
C8 C9 N2 C6 -0.8(3) . . . . ?
C5 C6 N2 C9 -178.6(2) . . . . ?
C7 C6 N2 C9 0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 F3 0.93 2.61 3.398(3) 143.4 4_655
C9 H9 F5 0.93 2.48 3.387(3) 164.0 3_565
N1 H1A N2 0.850(17) 2.16(2) 2.736(4) 125(2) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.047
