# 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_xb7619
_database_code_depnum_ccdc_archive 'CCDC 1418014'
_audit_update_record             
;
2015-08-11 deposited with the CCDC.
2016-02-29 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 H12 N O'
_chemical_formula_weight         222.26

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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'

_cell_length_a                   5.764(3)
_cell_length_b                   13.551(7)
_cell_length_c                   15.030(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1173.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    933
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      19.74

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9761
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_process_details   
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5784
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_sigmaI/netI    0.0859
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2075
_reflns_number_gt                1223
_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)+(0.0736P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(5)
_refine_ls_number_reflns         2075
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1557
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
N1 N 1.0127(8) 0.3609(3) 0.7745(3) 0.0668(11) Uani 1 1 d . . .
O1 O 0.8741(6) 0.07586(19) 0.7182(2) 0.0881(11) Uani 1 1 d . . .
C1 C 0.8782(10) 0.3650(4) 0.9886(4) 0.0928(16) Uani 1 1 d . . .
H1 H 1.0168 0.3315 0.9980 0.111 Uiso 1 1 calc R . .
C2 C 0.7792(12) 0.4159(4) 1.0564(4) 0.0970(17) Uani 1 1 d . . .
H2 H 0.8512 0.4175 1.1118 0.116 Uiso 1 1 calc R . .
C3 C 0.5819(12) 0.4632(4) 1.0446(4) 0.0900(18) Uani 1 1 d . . .
H3 H 0.5167 0.4975 1.0920 0.108 Uiso 1 1 calc R . .
C4 C 0.4726(10) 0.4630(4) 0.9654(5) 0.0935(17) Uani 1 1 d . . .
H4 H 0.3331 0.4965 0.9575 0.112 Uiso 1 1 calc R . .
C5 C 0.5748(12) 0.4113(4) 0.8956(4) 0.0875(17) Uani 1 1 d . . .
H5 H 0.5028 0.4102 0.8403 0.105 Uiso 1 1 calc R . .
C6 C 0.7768(11) 0.3627(3) 0.9072(4) 0.0757(14) Uani 1 1 d . . .
C7 C 0.8878(17) 0.3057(5) 0.8321(5) 0.174(4) Uani 1 1 d . . .
H7 H 1.0191 0.2794 0.8661 0.209 Uiso 1 1 calc R . .
C8 C 0.7938(9) 0.2151(3) 0.8062(3) 0.0746(14) Uani 1 1 d . . .
H8A H 0.6365 0.2261 0.7855 0.089 Uiso 1 1 calc R . .
H8B H 0.7855 0.1726 0.8580 0.089 Uiso 1 1 calc R . .
C9 C 0.9259(8) 0.1622(3) 0.7345(3) 0.0660(13) Uani 1 1 d . . .
C10 C 1.1023(8) 0.2171(3) 0.6877(3) 0.0617(12) Uani 1 1 d . . .
C11 C 1.2368(10) 0.1725(3) 0.6225(3) 0.0742(14) Uani 1 1 d . . .
H11 H 1.2152 0.1060 0.6097 0.089 Uiso 1 1 calc R . .
C12 C 1.3973(11) 0.2239(4) 0.5779(3) 0.0834(15) Uani 1 1 d . . .
H12 H 1.4838 0.1930 0.5338 0.100 Uiso 1 1 calc R . .
C13 C 1.4366(10) 0.3235(4) 0.5967(3) 0.0801(15) Uani 1 1 d . . .
H13 H 1.5488 0.3589 0.5657 0.096 Uiso 1 1 calc R . .
C14 C 1.3076(8) 0.3678(3) 0.6613(3) 0.0656(12) Uani 1 1 d . . .
H14 H 1.3316 0.4344 0.6733 0.079 Uiso 1 1 calc R . .
C15 C 1.1433(8) 0.3175(3) 0.7093(3) 0.0538(10) Uani 1 1 d . . .
H16 H 1.050(7) 0.412(4) 0.785(3) 0.064(14) Uiso 1 1 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
N1 C7 1.352(6) . ?
N1 C15 1.368(6) . ?
N1 H16 0.75(5) . ?
O1 C9 1.232(5) . ?
C1 C6 1.356(7) . ?
C1 C2 1.357(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.317(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.347(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.349(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(7) . ?
C7 C8 1.398(7) . ?
C7 H7 0.9800 . ?
C8 C9 1.501(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.443(6) . ?
C10 C11 1.389(6) . ?
C10 C15 1.418(5) . ?
C11 C12 1.338(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(6) . ?
C14 H14 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
C7 N1 C15 120.9(4) . . ?
C7 N1 H16 123(3) . . ?
C15 N1 H16 113(3) . . ?
C6 C1 C2 120.5(6) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.5(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 117.9(5) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 118.5(5) . . ?
C1 C6 C7 120.3(7) . . ?
C5 C6 C7 121.2(7) . . ?
N1 C7 C8 120.9(5) . . ?
N1 C7 C6 115.0(4) . . ?
C8 C7 C6 119.6(5) . . ?
N1 C7 H7 97.1 . . ?
C8 C7 H7 97.1 . . ?
C6 C7 H7 97.1 . . ?
C7 C8 C9 115.0(5) . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
O1 C9 C10 124.3(4) . . ?
O1 C9 C8 118.2(4) . . ?
C10 C9 C8 117.4(3) . . ?
C11 C10 C15 119.1(4) . . ?
C11 C10 C9 120.8(4) . . ?
C15 C10 C9 120.0(4) . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 121.0(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.7(5) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 122.2(4) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
N1 C15 C14 122.8(4) . . ?
N1 C15 C10 119.0(4) . . ?
C14 C15 C10 118.1(4) . . ?

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
C6 C1 C2 C3 0.6(8) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C2 C3 C4 C5 -0.1(8) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C2 C1 C6 C5 -0.6(8) . . . . ?
C2 C1 C6 C7 -179.9(5) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C4 C5 C6 C7 179.6(5) . . . . ?
C15 N1 C7 C8 -31.4(12) . . . . ?
C15 N1 C7 C6 172.7(6) . . . . ?
C1 C6 C7 N1 -99.0(8) . . . . ?
C5 C6 C7 N1 81.7(9) . . . . ?
C1 C6 C7 C8 104.7(9) . . . . ?
C5 C6 C7 C8 -74.6(9) . . . . ?
N1 C7 C8 C9 28.5(12) . . . . ?
C6 C7 C8 C9 -176.7(6) . . . . ?
C7 C8 C9 O1 168.9(6) . . . . ?
C7 C8 C9 C10 -12.4(8) . . . . ?
O1 C9 C10 C11 -3.5(7) . . . . ?
C8 C9 C10 C11 177.9(4) . . . . ?
O1 C9 C10 C15 177.7(4) . . . . ?
C8 C9 C10 C15 -0.9(6) . . . . ?
C15 C10 C11 C12 -2.6(7) . . . . ?
C9 C10 C11 C12 178.6(4) . . . . ?
C10 C11 C12 C13 1.1(8) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
C12 C13 C14 C15 1.1(7) . . . . ?
C7 N1 C15 C14 -166.5(6) . . . . ?
C7 N1 C15 C10 15.9(8) . . . . ?
C13 C14 C15 N1 179.8(4) . . . . ?
C13 C14 C15 C10 -2.5(6) . . . . ?
C11 C10 C15 N1 -179.1(4) . . . . ?
C9 C10 C15 N1 -0.2(6) . . . . ?
C11 C10 C15 C14 3.2(6) . . . . ?
C9 C10 C15 C14 -178.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_xb8279_0m
_database_code_depnum_ccdc_archive 'CCDC 1418015'
_audit_update_record             
;
2015-08-11 deposited with the CCDC.
2016-02-29 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 H11 F2 N O'
_chemical_formula_weight         259.25

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.816(2)
_cell_length_b                   8.648(3)
_cell_length_c                   10.567(3)
_cell_angle_alpha                91.038(5)
_cell_angle_beta                 97.022(5)
_cell_angle_gamma                96.930(5)
_cell_volume                     613.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    842
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      23.92

_exptl_crystal_description       colorless
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2994
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2125
_reflns_number_gt                1306
_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)+(0.1200P)²+0.1543P] 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       0.031(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2125
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.2200
_refine_ls_wR_factor_gt          0.1949
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 -0.0686(4) 0.3264(3) -0.0260(2) 0.0910(8) Uani 1 1 d . . .
F2 F -0.3160(3) 0.0613(3) -0.0607(2) 0.0884(8) Uani 1 1 d . . .
N1 N 0.1555(4) 0.2980(3) 0.4676(3) 0.0524(7) Uani 1 1 d . . .
H1 H 0.0551 0.3453 0.4409 0.063 Uiso 1 1 calc R . .
O1 O 0.7319(3) 0.2129(3) 0.5139(2) 0.0730(8) Uani 1 1 d . . .
C1 C 0.2707(4) 0.3415(3) 0.5808(3) 0.0474(8) Uani 1 1 d . . .
C2 C 0.1940(5) 0.4194(4) 0.6772(3) 0.0587(9) Uani 1 1 d . . .
H2 H 0.0653 0.4462 0.6629 0.070 Uiso 1 1 calc R . .
C3 C 0.3067(5) 0.4563(4) 0.7922(3) 0.0644(10) Uani 1 1 d . . .
H3 H 0.2531 0.5083 0.8551 0.077 Uiso 1 1 calc R . .
C4 C 0.4997(5) 0.4180(4) 0.8174(3) 0.0650(10) Uani 1 1 d . . .
H4 H 0.5733 0.4403 0.8970 0.078 Uiso 1 1 calc R . .
C5 C 0.5787(5) 0.3468(4) 0.7226(3) 0.0574(9) Uani 1 1 d . . .
H5 H 0.7091 0.3237 0.7376 0.069 Uiso 1 1 calc R . .
C6 C 0.4690(4) 0.3078(3) 0.6038(3) 0.0477(8) Uani 1 1 d . . .
C7 C 0.5571(4) 0.2375(4) 0.5000(3) 0.0541(9) Uani 1 1 d . . .
C8 C 0.4270(5) 0.2007(4) 0.3764(3) 0.0593(9) Uani 1 1 d . . .
H8A H 0.4665 0.1099 0.3357 0.071 Uiso 1 1 calc R . .
H8B H 0.4459 0.2875 0.3204 0.071 Uiso 1 1 calc R . .
C9 C 0.2084(5) 0.1691(4) 0.3940(3) 0.0560(9) Uani 1 1 d . . .
H9 H 0.1909 0.0753 0.4441 0.067 Uiso 1 1 calc R . .
C10 C 0.0702(5) 0.1410(4) 0.2711(3) 0.0537(9) Uani 1 1 d . . .
C11 C -0.0588(5) 0.0047(4) 0.2503(4) 0.0678(10) Uani 1 1 d . . .
H11 H -0.0568 -0.0703 0.3122 0.081 Uiso 1 1 calc R . .
C12 C -0.1904(6) -0.0230(5) 0.1402(4) 0.0737(11) Uani 1 1 d . . .
H12 H -0.2775 -0.1150 0.1286 0.088 Uiso 1 1 calc R . .
C13 C -0.1919(5) 0.0848(4) 0.0491(3) 0.0612(9) Uani 1 1 d . . .
C14 C -0.0649(5) 0.2211(4) 0.0672(3) 0.0584(9) Uani 1 1 d . . .
C15 C 0.0659(5) 0.2508(4) 0.1765(3) 0.0588(9) Uani 1 1 d . . .
H15 H 0.1513 0.3437 0.1874 0.071 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 C14 1.354(4) . ?
F2 C13 1.347(4) . ?
N1 C1 1.368(4) . ?
N1 C9 1.453(4) . ?
N1 H1 0.8600 . ?
O1 C7 1.227(3) . ?
C1 C2 1.398(4) . ?
C1 C6 1.411(4) . ?
C2 C3 1.367(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.469(5) . ?
C7 C8 1.492(4) . ?
C8 C9 1.517(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.506(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.380(5) . ?
C10 C15 1.391(5) . ?
C11 C12 1.378(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.352(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C14 C15 1.370(4) . ?
C15 H15 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
C1 N1 C9 117.8(3) . . ?
C1 N1 H1 121.1 . . ?
C9 N1 H1 121.1 . . ?
N1 C1 C2 120.8(3) . . ?
N1 C1 C6 120.9(3) . . ?
C2 C1 C6 118.3(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C7 121.6(3) . . ?
C1 C6 C7 119.0(3) . . ?
O1 C7 C6 121.1(3) . . ?
O1 C7 C8 121.5(3) . . ?
C6 C7 C8 117.4(3) . . ?
C7 C8 C9 112.2(3) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 110.4(3) . . ?
N1 C9 C8 109.0(3) . . ?
C10 C9 C8 114.1(3) . . ?
N1 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C8 C9 H9 107.7 . . ?
C11 C10 C15 118.1(3) . . ?
C11 C10 C9 120.2(3) . . ?
C15 C10 C9 121.7(3) . . ?
C12 C11 C10 121.7(4) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
F2 C13 C12 121.3(3) . . ?
F2 C13 C14 118.6(3) . . ?
C12 C13 C14 120.1(3) . . ?
F1 C14 C15 120.0(3) . . ?
F1 C14 C13 118.8(3) . . ?
C15 C14 C13 121.2(3) . . ?
C14 C15 C10 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?

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
C9 N1 C1 C2 -156.0(3) . . . . ?
C9 N1 C1 C6 23.3(4) . . . . ?
N1 C1 C2 C3 177.0(3) . . . . ?
C6 C1 C2 C3 -2.4(5) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 2.3(6) . . . . ?
C3 C4 C5 C6 -2.0(5) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 177.2(3) . . . . ?
N1 C1 C6 C5 -176.7(3) . . . . ?
C2 C1 C6 C5 2.6(4) . . . . ?
N1 C1 C6 C7 5.5(4) . . . . ?
C2 C1 C6 C7 -175.1(3) . . . . ?
C5 C6 C7 O1 -1.1(5) . . . . ?
C1 C6 C7 O1 176.6(3) . . . . ?
C5 C6 C7 C8 -179.8(3) . . . . ?
C1 C6 C7 C8 -2.1(4) . . . . ?
O1 C7 C8 C9 153.9(3) . . . . ?
C6 C7 C8 C9 -27.4(4) . . . . ?
C1 N1 C9 C10 -178.2(3) . . . . ?
C1 N1 C9 C8 -52.1(4) . . . . ?
C7 C8 C9 N1 52.5(4) . . . . ?
C7 C8 C9 C10 176.4(3) . . . . ?
N1 C9 C10 C11 -113.7(3) . . . . ?
C8 C9 C10 C11 123.1(4) . . . . ?
N1 C9 C10 C15 65.4(4) . . . . ?
C8 C9 C10 C15 -57.8(4) . . . . ?
C15 C10 C11 C12 -0.7(5) . . . . ?
C9 C10 C11 C12 178.4(3) . . . . ?
C10 C11 C12 C13 1.0(6) . . . . ?
C11 C12 C13 F2 179.0(3) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
F2 C13 C14 F1 -0.3(5) . . . . ?
C12 C13 C14 F1 179.5(3) . . . . ?
F2 C13 C14 C15 -179.4(3) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
F1 C14 C15 C10 -179.3(3) . . . . ?
C13 C14 C15 C10 -0.1(5) . . . . ?
C11 C10 C15 C14 0.2(5) . . . . ?
C9 C10 C15 C14 -178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.061
