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# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
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# 
#  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.
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#  fide research purposes only. It may contain copyright material
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data_4b
_audit_creation_method           SHELXL-97

####################################################################
#         Crystal Data                                             #
####################################################################


_chemical_name_systematic        
;

;
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 F N2 O2'
_chemical_formula_sum            'C18 H16 F N2 O2'
_chemical_formula_weight         311.33

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/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.2658(4)
_cell_length_b                   15.6654(7)
_cell_length_c                   12.7267(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.505(2)
_cell_angle_gamma                90.00
_cell_volume                     1571.63(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5977
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.04

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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 ApexII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            16484
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.28
_reflns_number_total             3531
_reflns_number_gt                2398
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'APEXII (Bruker, 2012)'
_computing_cell_refinement       'APEXII (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 & PLATON (Spek, 2003)'

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1161P)^2^+0.3673P] where P=(Fo^2^+2Fc^2^)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3531
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.2014
_refine_ls_wR_factor_gt          0.1738
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
H2 H 0.039(4) 0.2747(19) 1.035(3) 0.082(9) Uiso 1 1 d . . .
N1 N 0.2110(2) 0.21742(11) 0.88632(13) 0.0431(4) Uani 1 1 d . . .
O2 O 0.3122(2) -0.07284(11) 1.24051(14) 0.0642(5) Uani 1 1 d . . .
C1 C 0.0686(2) 0.18927(13) 0.92472(16) 0.0423(5) Uani 1 1 d . . .
H1 H -0.0169 0.1638 0.8618 0.051 Uiso 1 1 calc R . .
N2 N -0.0096(2) 0.25841(12) 0.96383(15) 0.0480(5) Uani 1 1 d . . .
F1 F 0.3940(2) -0.06685(10) 1.05792(13) 0.0762(5) Uani 1 1 d . . .
C12 C 0.1281(2) 0.12060(13) 1.01156(15) 0.0408(5) Uani 1 1 d . . .
O1 O 0.1126(2) 0.17258(11) 0.70773(12) 0.0603(5) Uani 1 1 d . . .
C6 C -0.0979(2) 0.32223(13) 0.89407(16) 0.0442(5) Uani 1 1 d . . .
C17 C 0.0768(3) 0.11697(14) 1.10555(17) 0.0490(5) Uani 1 1 d . . .
H17 H 0.0017 0.1579 1.1161 0.059 Uiso 1 1 calc R . .
C2 C 0.2204(3) 0.20608(13) 0.78292(16) 0.0447(5) Uani 1 1 d . . .
C11 C -0.1768(3) 0.30997(16) 0.78207(18) 0.0532(6) Uani 1 1 d . . .
H11 H -0.1634 0.2586 0.7491 0.064 Uiso 1 1 calc R . .
C13 C 0.2356(3) 0.05697(14) 0.99673(17) 0.0489(5) Uani 1 1 d . . .
H13 H 0.2710 0.0568 0.9339 0.059 Uiso 1 1 calc R . .
C15 C 0.2441(3) -0.00808(13) 1.16986(17) 0.0474(5) Uani 1 1 d . . .
C16 C 0.1343(3) 0.05401(15) 1.18395(18) 0.0540(6) Uani 1 1 d . . .
H16 H 0.0988 0.0535 1.2467 0.065 Uiso 1 1 calc R . .
C14 C 0.2895(3) -0.00531(14) 1.07402(18) 0.0493(5) Uani 1 1 d . . .
C7 C -0.1158(3) 0.40094(15) 0.93848(19) 0.0552(6) Uani 1 1 d . . .
H7 H -0.0601 0.4115 1.0125 0.066 Uiso 1 1 calc R . .
C10 C -0.2746(3) 0.37368(19) 0.7202(2) 0.0640(7) Uani 1 1 d . . .
H10 H -0.3279 0.3644 0.6456 0.077 Uiso 1 1 calc R . .
C5 C 0.3557(3) 0.26102(18) 0.95928(19) 0.0621(7) Uani 1 1 d . . .
H5 H 0.3753 0.2734 1.0335 0.075 Uiso 1 1 calc R . .
C3 C 0.3883(3) 0.24102(17) 0.77928(19) 0.0599(6) Uani 1 1 d . . .
H3 H 0.4336 0.2378 0.7208 0.072 Uiso 1 1 calc R . .
C8 C -0.2150(4) 0.46417(17) 0.8749(2) 0.0699(7) Uani 1 1 d . . .
H8 H -0.2272 0.5163 0.9066 0.084 Uiso 1 1 calc R . .
C9 C -0.2955(3) 0.45017(19) 0.7653(2) 0.0706(8) Uani 1 1 d . . .
H9 H -0.3634 0.4923 0.7224 0.085 Uiso 1 1 calc R . .
C18 C 0.2849(5) -0.0713(2) 1.3455(2) 0.0863(9) Uani 1 1 d . . .
H18A H 0.3281 -0.0189 1.3824 0.130 Uiso 1 1 calc R . .
H18B H 0.3426 -0.1186 1.3887 0.130 Uiso 1 1 calc R . .
H18C H 0.1656 -0.0754 1.3364 0.130 Uiso 1 1 calc R . .
C4 C 0.4674(4) 0.2820(2) 0.8892(2) 0.0801(9) Uani 1 1 d . . .
H4 H 0.5665 0.3142 0.9099 0.096 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
N1 0.0435(9) 0.0573(10) 0.0300(8) -0.0015(7) 0.0135(7) -0.0050(7)
O2 0.0777(11) 0.0625(10) 0.0551(10) 0.0150(8) 0.0239(9) 0.0020(8)
C1 0.0396(10) 0.0552(12) 0.0338(10) -0.0027(8) 0.0136(8) -0.0049(9)
N2 0.0503(10) 0.0627(11) 0.0314(9) 0.0021(8) 0.0127(8) 0.0086(8)
F1 0.0975(11) 0.0703(9) 0.0707(10) 0.0076(7) 0.0403(9) 0.0306(8)
C12 0.0373(9) 0.0514(11) 0.0344(10) -0.0042(8) 0.0121(8) -0.0059(8)
O1 0.0724(11) 0.0747(11) 0.0349(8) -0.0105(7) 0.0176(8) -0.0079(9)
C6 0.0374(10) 0.0595(12) 0.0401(11) 0.0061(9) 0.0185(8) -0.0019(9)
C17 0.0497(12) 0.0581(12) 0.0465(12) 0.0030(9) 0.0257(10) 0.0018(9)
C2 0.0542(12) 0.0500(11) 0.0328(10) 0.0017(8) 0.0174(9) 0.0045(9)
C11 0.0505(12) 0.0696(15) 0.0391(11) 0.0037(10) 0.0129(10) -0.0021(10)
C13 0.0565(12) 0.0574(13) 0.0375(10) -0.0037(9) 0.0212(10) -0.0003(10)
C15 0.0484(11) 0.0512(12) 0.0426(11) 0.0023(9) 0.0135(9) -0.0098(9)
C16 0.0608(13) 0.0641(14) 0.0445(12) 0.0044(10) 0.0273(11) -0.0039(11)
C14 0.0514(12) 0.0521(12) 0.0467(12) -0.0043(9) 0.0184(10) 0.0020(9)
C7 0.0562(13) 0.0609(14) 0.0494(13) 0.0007(10) 0.0173(11) 0.0004(10)
C10 0.0501(13) 0.0920(19) 0.0467(13) 0.0190(13) 0.0099(11) -0.0033(12)
C5 0.0510(13) 0.0962(18) 0.0403(12) -0.0100(12) 0.0155(10) -0.0213(12)
C3 0.0584(14) 0.0821(16) 0.0482(13) 0.0057(11) 0.0297(11) 0.0000(12)
C8 0.0707(16) 0.0633(15) 0.0782(19) 0.0075(13) 0.0262(14) 0.0090(13)
C9 0.0570(14) 0.0817(19) 0.0749(18) 0.0328(15) 0.0226(13) 0.0105(13)
C18 0.116(2) 0.092(2) 0.0527(15) 0.0234(15) 0.0280(16) 0.0037(18)
C4 0.0699(17) 0.117(2) 0.0607(16) -0.0091(15) 0.0309(14) -0.0405(16)

_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
N1 C2 1.353(2) . ?
N1 C5 1.446(3) . ?
N1 C1 1.471(2) . ?
O2 C15 1.360(3) . ?
O2 C18 1.421(3) . ?
C1 N2 1.426(3) . ?
C1 C12 1.514(3) . ?
C1 H1 0.9800 . ?
N2 C6 1.389(3) . ?
N2 H2 0.91(3) . ?
F1 C14 1.350(2) . ?
C12 C17 1.385(3) . ?
C12 C13 1.386(3) . ?
O1 C2 1.214(3) . ?
C6 C7 1.383(3) . ?
C6 C11 1.391(3) . ?
C17 C16 1.382(3) . ?
C17 H17 0.9300 . ?
C2 C3 1.505(3) . ?
C11 C10 1.374(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.362(3) . ?
C13 H13 0.9300 . ?
C15 C16 1.378(3) . ?
C15 C14 1.381(3) . ?
C16 H16 0.9300 . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C10 C9 1.362(4) . ?
C10 H10 0.9300 . ?
C5 C4 1.501(3) . ?
C5 H5 0.9300 . ?
C3 C4 1.498(4) . ?
C3 H3 0.9300 . ?
C8 C9 1.371(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C4 H4 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
C2 N1 C5 114.06(17) . . ?
C2 N1 C1 124.74(17) . . ?
C5 N1 C1 121.20(15) . . ?
C15 O2 C18 117.2(2) . . ?
N2 C1 N1 112.36(16) . . ?
N2 C1 C12 111.50(15) . . ?
N1 C1 C12 109.82(16) . . ?
N2 C1 H1 107.6 . . ?
N1 C1 H1 107.6 . . ?
C12 C1 H1 107.6 . . ?
C6 N2 C1 121.99(17) . . ?
C6 N2 H2 115.1(19) . . ?
C1 N2 H2 116.7(19) . . ?
C17 C12 C13 117.62(19) . . ?
C17 C12 C1 122.88(17) . . ?
C13 C12 C1 119.48(16) . . ?
C7 C6 N2 118.73(19) . . ?
C7 C6 C11 117.8(2) . . ?
N2 C6 C11 123.4(2) . . ?
C16 C17 C12 121.63(19) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
O1 C2 N1 125.44(19) . . ?
O1 C2 C3 126.75(18) . . ?
N1 C2 C3 107.80(19) . . ?
C10 C11 C6 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C14 C13 C12 120.06(18) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
O2 C15 C16 126.74(19) . . ?
O2 C15 C14 116.03(19) . . ?
C16 C15 C14 117.2(2) . . ?
C15 C16 C17 120.47(19) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
F1 C14 C13 119.15(18) . . ?
F1 C14 C15 117.91(19) . . ?
C13 C14 C15 122.94(19) . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C10 C11 121.7(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
N1 C5 C4 105.04(18) . . ?
N1 C5 H5 127.5 . . ?
C4 C5 H5 127.5 . . ?
C4 C3 C2 105.93(18) . . ?
C4 C3 H3 127.0 . . ?
C2 C3 H3 127.0 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C4 C5 106.7(2) . . ?
C3 C4 H4 126.6 . . ?
C5 C4 H4 126.6 . . ?

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
C2 N1 C1 N2 -120.6(2) . . . . ?
C5 N1 C1 N2 59.2(3) . . . . ?
C2 N1 C1 C12 114.6(2) . . . . ?
C5 N1 C1 C12 -65.6(2) . . . . ?
N1 C1 N2 C6 66.7(2) . . . . ?
C12 C1 N2 C6 -169.54(17) . . . . ?
N2 C1 C12 C17 14.0(3) . . . . ?
N1 C1 C12 C17 139.24(19) . . . . ?
N2 C1 C12 C13 -167.43(18) . . . . ?
N1 C1 C12 C13 -42.2(2) . . . . ?
C1 N2 C6 C7 -156.31(19) . . . . ?
C1 N2 C6 C11 26.9(3) . . . . ?
C13 C12 C17 C16 2.1(3) . . . . ?
C1 C12 C17 C16 -179.4(2) . . . . ?
C5 N1 C2 O1 -178.6(2) . . . . ?
C1 N1 C2 O1 1.2(3) . . . . ?
C5 N1 C2 C3 2.2(3) . . . . ?
C1 N1 C2 C3 -177.95(19) . . . . ?
C7 C6 C11 C10 -2.7(3) . . . . ?
N2 C6 C11 C10 174.15(19) . . . . ?
C17 C12 C13 C14 -1.2(3) . . . . ?
C1 C12 C13 C14 -179.78(19) . . . . ?
C18 O2 C15 C16 -8.1(3) . . . . ?
C18 O2 C15 C14 172.4(2) . . . . ?
O2 C15 C16 C17 179.1(2) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C12 C17 C16 C15 -0.7(4) . . . . ?
C12 C13 C14 F1 179.86(19) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
O2 C15 C14 F1 1.0(3) . . . . ?
C16 C15 C14 F1 -178.6(2) . . . . ?
O2 C15 C14 C13 -178.1(2) . . . . ?
C16 C15 C14 C13 2.4(3) . . . . ?
N2 C6 C7 C8 -174.1(2) . . . . ?
C11 C6 C7 C8 2.8(3) . . . . ?
C6 C11 C10 C9 0.9(3) . . . . ?
C2 N1 C5 C4 2.1(3) . . . . ?
C1 N1 C5 C4 -177.7(2) . . . . ?
O1 C2 C3 C4 175.2(2) . . . . ?
N1 C2 C3 C4 -5.7(3) . . . . ?
C6 C7 C8 C9 -1.2(4) . . . . ?
C11 C10 C9 C8 0.9(4) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C2 C3 C4 C5 6.8(3) . . . . ?
N1 C5 C4 C3 -5.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.056



_database_code_depnum_ccdc_archive 'CCDC 936474'