# 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_ATK-RK-4g
_database_code_depnum_ccdc_archive 'CCDC 1434638'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 F N O2'
_chemical_formula_sum            'C25 H22 F N O2'
_chemical_formula_weight         387.44

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.746(3)
_cell_length_b                   10.5892(9)
_cell_length_c                   16.2384(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.742(6)
_cell_angle_gamma                90.00
_cell_volume                     4110.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      15.87

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_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  '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            12686
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.1744
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         24.24
_reflns_number_total             2666
_reflns_number_gt                1013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0327P)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_number_reflns         2666
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2100
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_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 0.44576(9) 0.2733(2) 0.16099(17) 0.1076(10) Uani 1 1 d . . .
O1 O 0.12898(12) 0.1223(3) 0.1726(2) 0.0747(11) Uani 1 1 d . . .
O2 O 0.08313(15) 0.2941(2) 0.1760(2) 0.0608(9) Uani 1 1 d . . .
N1 N 0.33161(13) 0.0839(4) 0.3787(3) 0.0544(11) Uani 1 1 d . . .
C11 C 0.23429(19) 0.2265(4) 0.3151(3) 0.0464(12) Uani 1 1 d . . .
C10 C 0.22092(18) 0.0916(5) 0.4340(3) 0.0475(12) Uani 1 1 d . . .
C1 C 0.24941(19) 0.1291(5) 0.3860(3) 0.0457(12) Uani 1 1 d . . .
C20 C 0.18145(19) 0.3039(4) 0.2676(3) 0.0534(12) Uani 1 1 d . . .
H20A H 0.1834 0.3706 0.2285 0.064 Uiso 1 1 calc R . .
H20B H 0.1792 0.3435 0.3191 0.064 Uiso 1 1 calc R . .
C5 C 0.2401(2) -0.0145(5) 0.4978(3) 0.0560(13) Uani 1 1 d . . .
C16 C 0.41977(18) 0.1369(5) 0.2432(3) 0.0717(16) Uani 1 1 d . . .
H16 H 0.4423 0.0739 0.2433 0.086 Uiso 1 1 calc R . .
C14 C 0.35433(18) 0.2084(5) 0.2823(3) 0.0466(13) Uani 1 1 d . . .
C2 C 0.2978(2) 0.0583(5) 0.4117(3) 0.0485(12) Uani 1 1 d . . .
C4 C 0.2866(2) -0.0863(4) 0.5153(3) 0.0684(14) Uani 1 1 d . . .
H4 H 0.2974 -0.1588 0.5541 0.082 Uiso 1 1 calc R . .
C13 C 0.3178(2) 0.1804(5) 0.3175(3) 0.0461(12) Uani 1 1 d . . .
C12 C 0.2692(2) 0.2511(4) 0.2841(3) 0.0516(13) Uani 1 1 d . . .
H12 H 0.2603 0.3167 0.2396 0.062 Uiso 1 1 calc R . .
C15 C 0.38839(19) 0.1153(4) 0.2832(3) 0.0573(13) Uani 1 1 d . . .
H15 H 0.3904 0.0370 0.3110 0.069 Uiso 1 1 calc R . .
C7 C 0.1690(2) 0.0153(6) 0.5323(3) 0.0781(17) Uani 1 1 d . . .
H7 H 0.1515 -0.0098 0.5637 0.094 Uiso 1 1 calc R . .
C9 C 0.17572(19) 0.1579(4) 0.4250(3) 0.0623(14) Uani 1 1 d . . .
H9 H 0.1625 0.2297 0.3853 0.075 Uiso 1 1 calc R . .
C8 C 0.15032(18) 0.1216(5) 0.4721(4) 0.0730(15) Uani 1 1 d . . .
H8 H 0.1206 0.1683 0.4637 0.088 Uiso 1 1 calc R . .
C21 C 0.1289(2) 0.2273(5) 0.2016(3) 0.0553(15) Uani 1 1 d . . .
C17 C 0.4165(2) 0.2527(7) 0.2039(3) 0.0714(17) Uani 1 1 d . . .
C3 C 0.31507(16) -0.0492(4) 0.4757(3) 0.0635(14) Uani 1 1 d . . .
H3 H 0.3465 -0.0944 0.4903 0.076 Uiso 1 1 calc R . .
C6 C 0.2129(2) -0.0522(5) 0.5452(3) 0.0750(16) Uani 1 1 d . . .
H6 H 0.2253 -0.1236 0.5853 0.090 Uiso 1 1 calc R . .
C22 C 0.0267(2) 0.2448(5) 0.0993(4) 0.0692(14) Uani 1 1 d . . .
C18 C 0.3860(2) 0.3496(5) 0.2059(3) 0.0692(15) Uani 1 1 d . . .
H18 H 0.3864 0.4293 0.1822 0.083 Uiso 1 1 calc R . .
C19 C 0.35419(16) 0.3253(5) 0.2445(3) 0.0599(13) Uani 1 1 d . . .
H19 H 0.3322 0.3895 0.2449 0.072 Uiso 1 1 calc R . .
C23 C 0.01523(16) 0.1242(4) 0.1345(4) 0.1151(19) Uani 1 1 d . . .
H23A H 0.0213 0.1379 0.1983 0.173 Uiso 1 1 calc R . .
H23C H 0.0399 0.0591 0.1396 0.173 Uiso 1 1 calc R . .
H23B H -0.0229 0.0988 0.0882 0.173 Uiso 1 1 calc R . .
C24 C 0.02147(16) 0.2326(4) 0.0015(3) 0.122(2) Uani 1 1 d . . .
H24A H 0.0437 0.1628 0.0048 0.184 Uiso 1 1 calc R . .
H24B H 0.0343 0.3089 -0.0115 0.184 Uiso 1 1 calc R . .
H24C H -0.0170 0.2183 -0.0506 0.184 Uiso 1 1 calc R . .
C25 C -0.01063(15) 0.3512(4) 0.0935(3) 0.0995(16) Uani 1 1 d . . .
H25A H 0.0007 0.4293 0.0796 0.149 Uiso 1 1 calc R . .
H25C H -0.0073 0.3579 0.1556 0.149 Uiso 1 1 calc R . .
H25B H -0.0488 0.3336 0.0417 0.149 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 C17 1.376(5) . ?
O1 C21 1.208(5) . ?
O2 C21 1.341(5) . ?
O2 C22 1.487(4) . ?
N1 C13 1.323(4) . ?
N1 C2 1.371(4) . ?
C11 C12 1.376(4) . ?
C11 C1 1.421(5) . ?
C11 C20 1.508(5) . ?
C10 C9 1.412(4) . ?
C10 C5 1.416(5) . ?
C10 C1 1.465(5) . ?
C1 C2 1.425(5) . ?
C20 C21 1.512(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C5 C4 1.422(5) . ?
C5 C6 1.425(5) . ?
C16 C17 1.361(5) . ?
C16 C15 1.393(5) . ?
C16 H16 0.9300 . ?
C14 C19 1.381(5) . ?
C14 C15 1.384(4) . ?
C14 C13 1.479(5) . ?
C2 C3 1.432(5) . ?
C4 C3 1.351(4) . ?
C4 H4 0.9300 . ?
C13 C12 1.400(5) . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C7 C6 1.363(5) . ?
C7 C8 1.388(5) . ?
C7 H7 0.9300 . ?
C9 C8 1.374(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C17 C18 1.363(5) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C22 C23 1.509(5) . ?
C22 C24 1.515(5) . ?
C22 C25 1.522(5) . ?
C18 C19 1.389(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23B 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25C 0.9600 . ?
C25 H25B 0.9600 . ?

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
C21 O2 C22 120.1(4) . . ?
C13 N1 C2 117.6(4) . . ?
C12 C11 C1 118.5(4) . . ?
C12 C11 C20 116.2(4) . . ?
C1 C11 C20 125.3(5) . . ?
C9 C10 C5 115.6(5) . . ?
C9 C10 C1 124.4(5) . . ?
C5 C10 C1 119.9(5) . . ?
C11 C1 C2 115.4(4) . . ?
C11 C1 C10 128.2(5) . . ?
C2 C1 C10 116.5(5) . . ?
C11 C20 C21 113.3(4) . . ?
C11 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C11 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C10 C5 C4 120.8(5) . . ?
C10 C5 C6 120.6(5) . . ?
C4 C5 C6 118.6(6) . . ?
C17 C16 C15 118.2(5) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C19 C14 C15 118.1(5) . . ?
C19 C14 C13 121.6(5) . . ?
C15 C14 C13 120.2(5) . . ?
N1 C2 C1 124.8(5) . . ?
N1 C2 C3 114.0(5) . . ?
C1 C2 C3 121.3(5) . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C13 C12 121.6(4) . . ?
N1 C13 C14 117.6(5) . . ?
C12 C13 C14 120.8(5) . . ?
C11 C12 C13 122.0(4) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C6 C7 C8 119.7(5) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C8 C9 C10 123.1(5) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C9 C8 C7 120.2(5) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
O1 C21 O2 125.3(5) . . ?
O1 C21 C20 123.6(5) . . ?
O2 C21 C20 111.0(5) . . ?
C16 C17 C18 123.0(5) . . ?
C16 C17 F1 118.6(6) . . ?
C18 C17 F1 118.4(6) . . ?
C4 C3 C2 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O2 C22 C23 110.2(4) . . ?
O2 C22 C24 109.6(4) . . ?
C23 C22 C24 114.2(4) . . ?
O2 C22 C25 101.3(4) . . ?
C23 C22 C25 110.8(4) . . ?
C24 C22 C25 110.0(4) . . ?
C17 C18 C19 117.7(5) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C14 C19 C18 121.8(5) . . ?
C14 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25C C25 H25B 109.5 . . ?

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
C12 C11 C1 C2 -5.3(5) . . . . ?
C20 C11 C1 C2 172.6(3) . . . . ?
C12 C11 C1 C10 175.9(3) . . . . ?
C20 C11 C1 C10 -6.1(6) . . . . ?
C9 C10 C1 C11 -7.6(6) . . . . ?
C5 C10 C1 C11 175.4(4) . . . . ?
C9 C10 C1 C2 173.7(3) . . . . ?
C5 C10 C1 C2 -3.3(5) . . . . ?
C12 C11 C20 C21 112.2(4) . . . . ?
C1 C11 C20 C21 -65.7(4) . . . . ?
C9 C10 C5 C4 -177.9(3) . . . . ?
C1 C10 C5 C4 -0.6(5) . . . . ?
C9 C10 C5 C6 2.7(5) . . . . ?
C1 C10 C5 C6 179.9(3) . . . . ?
C13 N1 C2 C1 -1.0(5) . . . . ?
C13 N1 C2 C3 178.6(3) . . . . ?
C11 C1 C2 N1 4.9(5) . . . . ?
C10 C1 C2 N1 -176.2(3) . . . . ?
C11 C1 C2 C3 -174.7(3) . . . . ?
C10 C1 C2 C3 4.2(5) . . . . ?
C10 C5 C4 C3 4.0(6) . . . . ?
C6 C5 C4 C3 -176.5(3) . . . . ?
C2 N1 C13 C12 -2.5(5) . . . . ?
C2 N1 C13 C14 179.7(3) . . . . ?
C19 C14 C13 N1 -159.9(4) . . . . ?
C15 C14 C13 N1 22.5(5) . . . . ?
C19 C14 C13 C12 22.3(5) . . . . ?
C15 C14 C13 C12 -155.3(4) . . . . ?
C1 C11 C12 C13 2.3(5) . . . . ?
C20 C11 C12 C13 -175.8(3) . . . . ?
N1 C13 C12 C11 1.8(6) . . . . ?
C14 C13 C12 C11 179.6(3) . . . . ?
C19 C14 C15 C16 -2.8(6) . . . . ?
C13 C14 C15 C16 174.9(3) . . . . ?
C17 C16 C15 C14 0.7(6) . . . . ?
C5 C10 C9 C8 -1.8(5) . . . . ?
C1 C10 C9 C8 -179.0(3) . . . . ?
C10 C9 C8 C7 0.2(6) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C22 O2 C21 O1 -5.9(6) . . . . ?
C22 O2 C21 C20 170.6(3) . . . . ?
C11 C20 C21 O1 -14.9(6) . . . . ?
C11 C20 C21 O2 168.5(3) . . . . ?
C15 C16 C17 C18 2.9(7) . . . . ?
C15 C16 C17 F1 -177.7(3) . . . . ?
C5 C4 C3 C2 -3.2(6) . . . . ?
N1 C2 C3 C4 179.3(3) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C8 C7 C6 C5 0.2(6) . . . . ?
C10 C5 C6 C7 -2.0(6) . . . . ?
C4 C5 C6 C7 178.6(4) . . . . ?
C21 O2 C22 C23 64.2(5) . . . . ?
C21 O2 C22 C24 -62.2(5) . . . . ?
C21 O2 C22 C25 -178.4(3) . . . . ?
C16 C17 C18 C19 -4.1(7) . . . . ?
F1 C17 C18 C19 176.5(3) . . . . ?
C15 C14 C19 C18 1.6(6) . . . . ?
C13 C14 C19 C18 -176.1(3) . . . . ?
C17 C18 C19 C14 1.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        24.24
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046
