# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_gb16
_database_code_depnum_ccdc_archive 'CCDC 869820'
_audit_update_record             
;
2012-03-01 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;
#TrackingRef 'gb16final.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-(4-Fluorophenyl)-2-(4-fluorophenylamino)acetonitrile
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 F2 N2'
_chemical_formula_sum            'C14 H10 F2 N2'
_chemical_formula_weight         244.24

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   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'


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

_cell_length_a                   7.3859(3)
_cell_length_b                   13.2470(6)
_cell_length_c                   24.4599(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2393.18(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4853
_cell_measurement_theta_min      3.4910
_cell_measurement_theta_max      29.0192

_exptl_crystal_description       block-shaped
_exptl_crystal_colour            white
_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    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis RED'

_exptl_special_details           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12123
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2100
_reflns_number_gt                1430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro,Diff.Ltd,Ver 1.171.34.40'
_computing_cell_refinement       'CrysAlisPro, Diff.Ltd,Ver 1.171.34.40'
_computing_data_reduction        'CrysAlisPro, Diff.Ltd,Ver 1.171.34.40'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'PLATON(Spek,1999)& PARST(1995)'


_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)+(0.0623P)²+0.8614P] 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     SHELXL
_refine_ls_extinction_coef       0.0031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2100
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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 0.5506(3) 0.86786(15) -0.00811(8) 0.0432(6) Uani 1 1 d . . .
C2 C 0.3765(3) 0.82792(16) -0.03044(8) 0.0427(5) Uani 1 1 d . . .
H2 H 0.3732 0.7550 -0.0237 0.051 Uiso 1 1 calc R . .
C3 C 0.3642(3) 0.84476(17) -0.09158(8) 0.0435(5) Uani 1 1 d . . .
C4 C 0.4366(4) 0.92973(19) -0.11621(9) 0.0578(7) Uani 1 1 d . . .
H4 H 0.4966 0.9775 -0.0950 0.069 Uiso 1 1 calc R . .
C5 C 0.4208(4) 0.9444(2) -0.17195(10) 0.0682(8) Uani 1 1 d . . .
H5 H 0.4692 1.0014 -0.1886 0.082 Uiso 1 1 calc R . .
C6 C 0.3324(4) 0.8731(2) -0.20181(9) 0.0658(8) Uani 1 1 d . . .
C7 C 0.2589(4) 0.7894(2) -0.17913(10) 0.0740(8) Uani 1 1 d . . .
H7 H 0.1983 0.7423 -0.2006 0.089 Uiso 1 1 calc R . .
C8 C 0.2757(4) 0.7753(2) -0.12337(9) 0.0605(7) Uani 1 1 d . . .
H8 H 0.2265 0.7180 -0.1072 0.073 Uiso 1 1 calc R . .
F9 F 0.3189(3) 0.88674(14) -0.25674(6) 0.1026(7) Uani 1 1 d . . .
N10 N 0.6801(3) 0.89992(15) 0.01030(8) 0.0532(5) Uani 1 1 d . . .
N11 N 0.2228(2) 0.87324(14) -0.00283(7) 0.0461(5) Uani 1 1 d . . .
H11 H 0.1389 0.9019 -0.0216 0.055 Uiso 1 1 calc R . .
C12 C 0.2101(3) 0.87058(16) 0.05491(8) 0.0426(5) Uani 1 1 d . . .
C13 C 0.1076(3) 0.94471(19) 0.08056(9) 0.0533(6) Uani 1 1 d . . .
H13 H 0.0541 0.9953 0.0597 0.064 Uiso 1 1 calc R . .
C14 C 0.0842(3) 0.9443(2) 0.13658(10) 0.0631(7) Uani 1 1 d . . .
H14 H 0.0159 0.9941 0.1537 0.076 Uiso 1 1 calc R . .
C15 C 0.1633(4) 0.8694(2) 0.16628(10) 0.0669(8) Uani 1 1 d . . .
C16 C 0.2661(4) 0.7961(2) 0.14280(9) 0.0651(7) Uani 1 1 d . . .
H16 H 0.3199 0.7464 0.1642 0.078 Uiso 1 1 calc R . .
C17 C 0.2898(3) 0.79663(17) 0.08642(9) 0.0517(6) Uani 1 1 d . . .
H17 H 0.3597 0.7468 0.0699 0.062 Uiso 1 1 calc R . .
F18 F 0.1383(3) 0.86864(15) 0.22149(6) 0.1095(7) 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
C1 0.0523(14) 0.0402(12) 0.0370(11) 0.0025(9) -0.0019(10) 0.0049(11)
C2 0.0477(13) 0.0408(12) 0.0397(11) -0.0008(10) -0.0036(9) -0.0025(10)
C3 0.0450(12) 0.0484(13) 0.0371(11) -0.0050(10) -0.0005(9) 0.0000(10)
C4 0.0761(18) 0.0546(15) 0.0428(12) -0.0012(11) -0.0058(11) -0.0136(13)
C5 0.089(2) 0.0702(17) 0.0452(14) 0.0082(13) -0.0013(13) -0.0130(15)
C6 0.0806(19) 0.084(2) 0.0329(12) -0.0040(13) -0.0025(12) 0.0018(16)
C7 0.091(2) 0.084(2) 0.0467(14) -0.0171(14) -0.0063(14) -0.0233(17)
C8 0.0725(17) 0.0623(16) 0.0468(13) -0.0076(12) 0.0004(12) -0.0194(14)
F9 0.1471(18) 0.1249(15) 0.0359(8) 0.0000(8) -0.0084(9) -0.0165(13)
N10 0.0533(12) 0.0515(12) 0.0547(12) 0.0008(10) -0.0107(10) 0.0044(10)
N11 0.0428(10) 0.0621(13) 0.0333(9) 0.0000(8) -0.0062(7) 0.0075(9)
C12 0.0416(12) 0.0486(13) 0.0377(11) 0.0002(10) -0.0035(9) -0.0060(10)
C13 0.0498(14) 0.0642(15) 0.0458(13) 0.0004(12) -0.0049(10) 0.0090(12)
C14 0.0655(17) 0.0754(18) 0.0484(13) -0.0081(13) 0.0052(12) 0.0084(14)
C15 0.085(2) 0.081(2) 0.0346(13) 0.0037(12) 0.0004(12) -0.0035(16)
C16 0.0819(19) 0.0685(17) 0.0450(13) 0.0134(13) -0.0091(13) 0.0025(15)
C17 0.0602(15) 0.0495(13) 0.0455(12) 0.0016(11) -0.0024(11) 0.0010(12)
F18 0.1623(19) 0.1294(16) 0.0368(8) 0.0053(9) 0.0078(9) 0.0174(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
C1 N10 1.140(3) . ?
C1 C2 1.494(3) . ?
C2 N11 1.451(3) . ?
C2 C3 1.515(3) . ?
C2 H2 0.9800 . ?
C3 C8 1.370(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.354(4) . ?
C6 F9 1.359(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
N11 C12 1.416(2) . ?
N11 H11 0.8600 . ?
C12 C17 1.378(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(4) . ?
C15 F18 1.363(3) . ?
C16 C17 1.390(3) . ?
C16 H16 0.9300 . ?
C17 H17 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
N10 C1 C2 177.7(2) . . ?
N11 C2 C1 110.90(16) . . ?
N11 C2 C3 110.57(17) . . ?
C1 C2 C3 111.15(17) . . ?
N11 C2 H2 108.0 . . ?
C1 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C8 C3 C4 118.9(2) . . ?
C8 C3 C2 119.3(2) . . ?
C4 C3 C2 121.74(19) . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C7 C6 F9 119.0(2) . . ?
C7 C6 C5 122.7(2) . . ?
F9 C6 C5 118.3(2) . . ?
C6 C7 C8 118.6(2) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C3 C8 C7 120.8(2) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C12 N11 C2 120.36(17) . . ?
C12 N11 H11 119.8 . . ?
C2 N11 H11 119.8 . . ?
C17 C12 C13 118.8(2) . . ?
C17 C12 N11 123.18(19) . . ?
C13 C12 N11 117.95(19) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C16 C15 C14 122.3(2) . . ?
C16 C15 F18 119.3(2) . . ?
C14 C15 F18 118.4(2) . . ?
C15 C16 C17 119.1(2) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C12 C17 C16 120.3(2) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?

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
N10 C1 C2 N11 8(6) . . . . ?
N10 C1 C2 C3 132(6) . . . . ?
N11 C2 C3 C8 -89.8(3) . . . . ?
C1 C2 C3 C8 146.6(2) . . . . ?
N11 C2 C3 C4 88.8(2) . . . . ?
C1 C2 C3 C4 -34.8(3) . . . . ?
C8 C3 C4 C5 -0.2(4) . . . . ?
C2 C3 C4 C5 -178.8(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C4 C5 C6 F9 -179.1(2) . . . . ?
F9 C6 C7 C8 179.0(3) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C4 C3 C8 C7 0.1(4) . . . . ?
C2 C3 C8 C7 178.7(2) . . . . ?
C6 C7 C8 C3 0.3(4) . . . . ?
C1 C2 N11 C12 -53.5(2) . . . . ?
C3 C2 N11 C12 -177.25(18) . . . . ?
C2 N11 C12 C17 -26.8(3) . . . . ?
C2 N11 C12 C13 155.2(2) . . . . ?
C17 C12 C13 C14 -0.5(3) . . . . ?
N11 C12 C13 C14 177.6(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C13 C14 C15 F18 -179.3(2) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
F18 C15 C16 C17 179.4(2) . . . . ?
C13 C12 C17 C16 0.6(3) . . . . ?
N11 C12 C17 C16 -177.4(2) . . . . ?
C15 C16 C17 C12 0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.035
