# 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_352
_database_code_depnum_ccdc_archive 'CCDC 1455899'
_audit_update_record             
;
2016-02-26 deposited with the CCDC.
2016-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (E)-N-(2-fluoro-2-(1H-imidazol-1-yl)vinyl)-1,1-diphenylmethanimine 
;
_chemical_name_common            ?
_chemical_melting_point          375-378
_chemical_formula_moiety         'C18 H14 F N3'
_chemical_formula_sum            'C18 H14 F N3'
_chemical_formula_weight         291.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   11.382(2)
_cell_length_b                   9.834(2)
_cell_length_c                   14.321(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.40(3)
_cell_angle_gamma                90.00
_cell_volume                     1512.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5838
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      66.94

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5965
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7025
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         65.96
_reflns_number_total             2566
_reflns_number_gt                2472
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0646P)²+0.2557P] 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       0.117(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2566
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
F1 F 0.48885(10) 0.30191(9) 0.21416(9) 0.0776(4) Uani 1 1 d . . .
N1 N 0.60604(10) -0.00998(12) 0.15123(9) 0.0507(3) Uani 1 1 d . . .
N2 N 0.42807(11) 0.09085(11) 0.23964(9) 0.0490(3) Uani 1 1 d . . .
N3 N 0.35752(12) -0.07814(13) 0.30770(10) 0.0610(4) Uani 1 1 d . . .
C1 C 0.50732(14) 0.16845(14) 0.20491(11) 0.0539(4) Uani 1 1 d . . .
C2 C 0.59145(14) 0.12727(14) 0.16606(11) 0.0558(4) Uani 1 1 d . . .
H2A H 0.6411 0.1907 0.1486 0.067 Uiso 1 1 calc R . .
C3 C 0.68222(11) -0.05118(14) 0.10783(9) 0.0467(3) Uani 1 1 d . . .
C4 C 0.75673(12) 0.04310(13) 0.06720(10) 0.0467(3) Uani 1 1 d . . .
C5 C 0.88254(14) 0.0637(2) 0.11463(14) 0.0727(5) Uani 1 1 d . . .
H5A H 0.9236 0.0177 0.1731 0.087 Uiso 1 1 calc R . .
C6 C 0.94768(16) 0.1529(2) 0.07507(17) 0.0855(6) Uani 1 1 d . . .
H6A H 1.0322 0.1672 0.1078 0.103 Uiso 1 1 calc R . .
C7 C 0.88927(17) 0.22011(18) -0.01136(14) 0.0728(5) Uani 1 1 d . . .
H7A H 0.9337 0.2794 -0.0377 0.087 Uiso 1 1 calc R . .
C8 C 0.76534(17) 0.19954(17) -0.05858(12) 0.0666(4) Uani 1 1 d . . .
H8A H 0.7252 0.2449 -0.1176 0.080 Uiso 1 1 calc R . .
C9 C 0.69892(14) 0.11215(15) -0.01977(11) 0.0574(4) Uani 1 1 d . . .
H9A H 0.6142 0.0996 -0.0526 0.069 Uiso 1 1 calc R . .
C10 C 0.69095(12) -0.19957(14) 0.09303(9) 0.0484(4) Uani 1 1 d . . .
C11 C 0.76389(15) -0.25215(16) 0.04081(11) 0.0609(4) Uani 1 1 d . . .
H11A H 0.8102 -0.1934 0.0158 0.073 Uiso 1 1 calc R . .
C12 C 0.76872(18) -0.38994(19) 0.02548(13) 0.0740(5) Uani 1 1 d . . .
H12A H 0.8183 -0.4233 -0.0095 0.089 Uiso 1 1 calc R . .
C13 C 0.70095(19) -0.47814(18) 0.06145(14) 0.0769(5) Uani 1 1 d . . .
H13A H 0.7045 -0.5712 0.0511 0.092 Uiso 1 1 calc R . .
C14 C 0.62762(19) -0.42800(17) 0.11302(15) 0.0756(5) Uani 1 1 d . . .
H14A H 0.5810 -0.4875 0.1371 0.091 Uiso 1 1 calc R . .
C15 C 0.62275(16) -0.29060(16) 0.12924(13) 0.0617(4) Uani 1 1 d . . .
H15A H 0.5734 -0.2581 0.1647 0.074 Uiso 1 1 calc R . .
C16 C 0.45305(14) -0.03093(15) 0.28790(11) 0.0557(4) Uani 1 1 d . . .
H16A H 0.5296 -0.0749 0.3046 0.067 Uiso 1 1 calc R . .
C17 C 0.26573(14) 0.01699(16) 0.27022(12) 0.0617(4) Uani 1 1 d . . .
H17A H 0.1857 0.0101 0.2735 0.074 Uiso 1 1 calc R . .
C18 C 0.30556(13) 0.12074(15) 0.22838(11) 0.0557(4) Uani 1 1 d . . .
H18A H 0.2604 0.1969 0.1981 0.067 Uiso 1 1 calc R . .


_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 C1 1.3427(17) . ?
N1 C3 1.2885(17) . ?
N1 C2 1.3849(19) . ?
N2 C16 1.3646(19) . ?
N2 C18 1.3811(18) . ?
N2 C1 1.3934(18) . ?
N3 C16 1.2973(19) . ?
N3 C17 1.372(2) . ?
C1 C2 1.321(2) . ?
C2 H2A 0.9300 . ?
C3 C10 1.483(2) . ?
C3 C4 1.4984(18) . ?
C4 C9 1.379(2) . ?
C4 C5 1.381(2) . ?
C5 C6 1.385(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.365(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.362(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.378(2) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C11 1.3888(19) . ?
C10 C15 1.393(2) . ?
C11 C12 1.377(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.370(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(2) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.336(2) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
C3 N1 C2 120.97(12) . . ?
C16 N2 C18 106.16(12) . . ?
C16 N2 C1 127.64(12) . . ?
C18 N2 C1 126.16(12) . . ?
C16 N3 C17 104.78(13) . . ?
C2 C1 F1 120.03(13) . . ?
C2 C1 N2 128.93(13) . . ?
F1 C1 N2 111.04(12) . . ?
C1 C2 N1 120.27(13) . . ?
C1 C2 H2A 119.9 . . ?
N1 C2 H2A 119.9 . . ?
N1 C3 C10 117.79(11) . . ?
N1 C3 C4 123.45(12) . . ?
C10 C3 C4 118.68(11) . . ?
C9 C4 C5 118.54(13) . . ?
C9 C4 C3 119.58(12) . . ?
C5 C4 C3 121.88(13) . . ?
C4 C5 C6 120.02(16) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C5 120.77(16) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C8 C7 C6 119.37(15) . . ?
C8 C7 H7A 120.3 . . ?
C6 C7 H7A 120.3 . . ?
C7 C8 C9 120.60(15) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
C8 C9 C4 120.69(14) . . ?
C8 C9 H9A 119.7 . . ?
C4 C9 H9A 119.7 . . ?
C11 C10 C15 117.90(14) . . ?
C11 C10 C3 121.60(12) . . ?
C15 C10 C3 120.47(12) . . ?
C12 C11 C10 121.00(15) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C13 C12 C11 120.39(16) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C14 119.50(16) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C15 C14 C13 120.55(17) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C14 C15 C10 120.65(15) . . ?
C14 C15 H15A 119.7 . . ?
C10 C15 H15A 119.7 . . ?
N3 C16 N2 112.09(13) . . ?
N3 C16 H16A 124.0 . . ?
N2 C16 H16A 124.0 . . ?
C18 C17 N3 111.61(13) . . ?
C18 C17 H17A 124.2 . . ?
N3 C17 H17A 124.2 . . ?
C17 C18 N2 105.36(13) . . ?
C17 C18 H18A 127.3 . . ?
N2 C18 H18A 127.3 . . ?

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
C16 N2 C1 C2 36.1(2) . . . . ?
C18 N2 C1 C2 -141.35(17) . . . . ?
C16 N2 C1 F1 -144.50(14) . . . . ?
C18 N2 C1 F1 38.04(19) . . . . ?
F1 C1 C2 N1 -176.38(14) . . . . ?
N2 C1 C2 N1 3.0(3) . . . . ?
C3 N1 C2 C1 175.66(14) . . . . ?
C2 N1 C3 C10 -178.90(12) . . . . ?
C2 N1 C3 C4 -2.2(2) . . . . ?
N1 C3 C4 C9 -75.07(18) . . . . ?
C10 C3 C4 C9 101.59(16) . . . . ?
N1 C3 C4 C5 104.68(18) . . . . ?
C10 C3 C4 C5 -78.66(18) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 -179.30(17) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C4 -0.5(3) . . . . ?
C5 C4 C9 C8 0.2(2) . . . . ?
C3 C4 C9 C8 179.91(14) . . . . ?
N1 C3 C10 C11 175.36(13) . . . . ?
C4 C3 C10 C11 -1.5(2) . . . . ?
N1 C3 C10 C15 -2.8(2) . . . . ?
C4 C3 C10 C15 -179.70(13) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
C3 C10 C11 C12 -178.35(15) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C10 0.6(3) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C3 C10 C15 C14 177.98(15) . . . . ?
C17 N3 C16 N2 0.26(17) . . . . ?
C18 N2 C16 N3 -0.30(17) . . . . ?
C1 N2 C16 N3 -178.16(13) . . . . ?
C16 N3 C17 C18 -0.11(18) . . . . ?
N3 C17 C18 N2 -0.07(17) . . . . ?
C16 N2 C18 C17 0.21(16) . . . . ?
C1 N2 C18 C17 178.11(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        65.96
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.068
