# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_SJ_AA_121
_database_code_depnum_ccdc_archive 'CCDC 1063690'
_audit_update_record             
;
2015-05-26 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2015-03-08T16:22:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17  H13  N1  O1  F4'
_chemical_formula_sum            'C17 H13 F4 N O'
_chemical_formula_weight         323.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3417(10)
_cell_length_b                   10.0649(14)
_cell_length_c                   10.3982(14)
_cell_angle_alpha                75.006(4)
_cell_angle_beta                 89.015(4)
_cell_angle_gamma                78.726(4)
_cell_volume                     727.42(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       needle
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_number            21469
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.029
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_number_total             2970
_reflns_number_gt                1980
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+0.2254P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2970
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8355(2) 0.35695(13) 0.40087(12) 0.0529(4) Uani 1 d . .
F1 F 0.8564(2) -0.13739(13) 0.90752(13) 0.0828(5) Uani 1 d . .
F4 F 0.7044(2) 0.33927(17) 0.05514(15) 0.0985(6) Uani 1 d . .
F2 F 0.6803(3) 0.21170(14) 0.24941(17) 0.1080(6) Uani 1 d . .
N1 N 0.7343(2) 0.48847(16) 0.55243(15) 0.0461(4) Uani 1 d . .
F3 F 0.4390(2) 0.32634(18) 0.13176(19) 0.1037(6) Uani 1 d . .
C1 C 0.7232(2) 0.61344(18) 0.45058(18) 0.0403(4) Uani 1 d . .
C11 C 0.7867(2) 0.37246(18) 0.52249(16) 0.0381(4) Uani 1 d . .
C12 C 0.8065(2) 0.23672(18) 0.62345(17) 0.0388(4) Uani 1 d . .
C7 C 0.7867(3) 0.47312(18) 0.28195(17) 0.0432(5) Uani 1 d . .
C17 C 0.8362(3) 0.11095(19) 0.58772(19) 0.0480(5) Uani 1 d . .
H17 H 0.8452 0.1117 0.4963 0.058 Uiso 1 calc . .
C6 C 0.7491(3) 0.61229(18) 0.31841(18) 0.0431(4) Uani 1 d . .
C8 C 0.6065(3) 0.4573(2) 0.2206(2) 0.0495(5) Uani 1 d . .
H8A H 0.5112 0.4563 0.2892 0.059 Uiso 1 calc . .
H8B H 0.5642 0.5425 0.1471 0.059 Uiso 1 calc . .
C13 C 0.7932(3) 0.2338(2) 0.75760(18) 0.0489(5) Uani 1 d . .
H13 H 0.7727 0.3192 0.7835 0.059 Uiso 1 calc . .
C2 C 0.6838(3) 0.7405(2) 0.4846(2) 0.0512(5) Uani 1 d . .
H2 H 0.6683 0.7411 0.5754 0.061 Uiso 1 calc . .
C3 C 0.6671(3) 0.8657(2) 0.3882(2) 0.0549(5) Uani 1 d . .
H3 H 0.6396 0.9521 0.4123 0.066 Uiso 1 calc . .
C14 C 0.8096(3) 0.1082(2) 0.8532(2) 0.0572(6) Uani 1 d . .
H14 H 0.8005 0.106 0.945 0.069 Uiso 1 calc . .
C4 C 0.6905(3) 0.8648(2) 0.2570(2) 0.0598(6) Uani 1 d . .
H4 H 0.6781 0.9509 0.19 0.072 Uiso 1 calc . .
C10 C 0.9547(3) 0.4585(2) 0.1963(2) 0.0583(6) Uani 1 d . .
H10A H 1.0627 0.4723 0.2417 0.087 Uiso 1 calc . .
H10B H 0.9299 0.5291 0.1106 0.087 Uiso 1 calc . .
H10C H 0.9803 0.3645 0.1812 0.087 Uiso 1 calc . .
C16 C 0.8531(3) -0.0152(2) 0.6828(2) 0.0542(5) Uani 1 d . .
H16 H 0.8738 -0.1013 0.6581 0.065 Uiso 1 calc . .
C5 C 0.7319(3) 0.7390(2) 0.2224(2) 0.0585(6) Uani 1 d . .
H5 H 0.7489 0.7393 0.1315 0.07 Uiso 1 calc . .
C15 C 0.8391(3) -0.0133(2) 0.8134(2) 0.0530(5) Uani 1 d . .
C9 C 0.6095(3) 0.3323(2) 0.1670(2) 0.0641(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C11 1.348(2) . ?
O1 C7 1.459(2) . ?
F1 C15 1.358(2) . ?
F4 C9 1.338(3) . ?
F2 C9 1.307(3) . ?
N1 C11 1.271(2) . ?
N1 C1 1.409(2) . ?
F3 C9 1.327(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.390(3) . ?
C11 C12 1.475(2) . ?
C12 C17 1.386(2) . ?
C12 C13 1.390(3) . ?
C7 C10 1.515(3) . ?
C7 C6 1.517(2) . ?
C7 C8 1.532(3) . ?
C17 C16 1.378(3) . ?
C17 H17 0.95 . ?
C6 C5 1.387(3) . ?
C8 C9 1.499(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C13 C14 1.376(3) . ?
C13 H13 0.95 . ?
C2 C3 1.377(3) . ?
C2 H2 0.95 . ?
C3 C4 1.375(3) . ?
C3 H3 0.95 . ?
C14 C15 1.367(3) . ?
C14 H14 0.95 . ?
C4 C5 1.380(3) . ?
C4 H4 0.95 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C16 C15 1.365(3) . ?
C16 H16 0.95 . ?
C5 H5 0.95 . ?

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
C11 O1 C7 121.02(13) . . ?
C11 N1 C1 118.15(15) . . ?
C6 C1 C2 119.74(17) . . ?
C6 C1 N1 121.71(16) . . ?
C2 C1 N1 118.55(16) . . ?
N1 C11 O1 125.89(16) . . ?
N1 C11 C12 121.77(16) . . ?
O1 C11 C12 112.30(14) . . ?
C17 C12 C13 118.78(17) . . ?
C17 C12 C11 121.48(16) . . ?
C13 C12 C11 119.73(16) . . ?
O1 C7 C10 104.03(14) . . ?
O1 C7 C6 110.55(14) . . ?
C10 C7 C6 112.08(16) . . ?
O1 C7 C8 107.60(15) . . ?
C10 C7 C8 114.80(16) . . ?
C6 C7 C8 107.66(15) . . ?
C16 C17 C12 121.01(18) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C5 C6 C1 118.94(17) . . ?
C5 C6 C7 121.75(17) . . ?
C1 C6 C7 119.26(16) . . ?
C9 C8 C7 118.47(17) . . ?
C9 C8 H8A 107.7 . . ?
C7 C8 H8A 107.7 . . ?
C9 C8 H8B 107.7 . . ?
C7 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
C14 C13 C12 120.59(18) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C3 C2 C1 120.71(19) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.64(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C15 C14 C13 118.62(18) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C3 C4 C5 120.07(19) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C16 C17 118.26(18) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
F1 C15 C16 118.47(18) . . ?
F1 C15 C14 118.80(18) . . ?
C16 C15 C14 122.73(18) . . ?
F2 C9 F3 107.5(2) . . ?
F2 C9 F4 106.5(2) . . ?
F3 C9 F4 104.46(19) . . ?
F2 C9 C8 114.70(18) . . ?
F3 C9 C8 110.58(19) . . ?
F4 C9 C8 112.4(2) . . ?



# END of CIF
####################################################################### 
# 
# 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_SJ_231
_database_code_depnum_ccdc_archive 'CCDC 1402832'
_audit_update_record             
;
2015-05-26 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2015-05-25T20:26:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22  H16  N1  O1  F3'
_chemical_formula_sum            'C22 H16 F3 N O'
_chemical_formula_weight         367.36

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   12.8017(8)
_cell_length_b                   9.6398(6)
_cell_length_c                   15.4464(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.362(4)
_cell_angle_gamma                90
_cell_volume                     1838.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.177
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_number            46069
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.406
_diffrn_reflns_theta_max         25.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3384
_reflns_number_gt                1881
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+0.9354P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3384
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.3
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21202(19) 0.6369(2) 0.72608(13) 0.0643(7) Uani 1 1 d . . . . .
N1 N 0.25265(17) 0.4147(2) 0.70356(14) 0.0400(6) Uani 1 1 d . . . . .
H1 H 0.2787 0.3349 0.7276 0.048 Uiso 1 1 calc R U . . .
F2 F 0.60795(16) 0.6873(2) 0.66494(16) 0.0976(7) Uani 1 1 d . . . . .
F1 F 0.5383(2) 0.7688(3) 0.76218(17) 0.1313(11) Uani 1 1 d . . . . .
F3 F 0.5270(2) 0.8772(2) 0.6403(2) 0.1262(10) Uani 1 1 d . . . . .
C6 C 0.2873(2) 0.5031(3) 0.56599(17) 0.0393(7) Uani 1 1 d . . . . .
C17 C 0.2678(2) 0.4936(3) 0.85517(18) 0.0414(7) Uani 1 1 d . . . . .
C1 C 0.2215(2) 0.4299(3) 0.60786(17) 0.0390(7) Uani 1 1 d . . . . .
C10 C 0.4779(2) 0.4359(3) 0.64657(19) 0.0422(7) Uani 1 1 d . . . . .
C16 C 0.2424(2) 0.5218(3) 0.75741(19) 0.0431(7) Uani 1 1 d . . . . .
C7 C 0.3975(2) 0.5501(3) 0.61736(17) 0.0413(7) Uani 1 1 d . . . . .
C8 C 0.4166(2) 0.6847(3) 0.63132(19) 0.0504(8) Uani 1 1 d . . . . .
H6 H 0.356 0.7444 0.6109 0.061 Uiso 1 1 calc R U . . .
C11 C 0.4901(2) 0.3378(3) 0.5839(2) 0.0524(8) Uani 1 1 d . . . . .
H7 H 0.448 0.345 0.5233 0.063 Uiso 1 1 calc R U . . .
C22 C 0.2087(3) 0.5654(3) 0.9041(2) 0.0553(8) Uani 1 1 d . . . . .
H16 H 0.1561 0.6316 0.875 0.066 Uiso 1 1 calc R U . . .
C2 C 0.1249(2) 0.3751(3) 0.5585(2) 0.0542(8) Uani 1 1 d . . . . .
H2 H 0.0809 0.3238 0.5879 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3453(2) 0.3998(3) 0.8993(2) 0.0542(8) Uani 1 1 d . . . . .
H12 H 0.3869 0.3506 0.8668 0.065 Uiso 1 1 calc R U . . .
C5 C 0.2513(2) 0.5235(3) 0.47380(19) 0.0527(8) Uani 1 1 d . . . . .
H5 H 0.2944 0.5756 0.4441 0.063 Uiso 1 1 calc R U . . .
C4 C 0.1544(3) 0.4696(3) 0.4250(2) 0.0610(9) Uani 1 1 d . . . . .
H4 H 0.1309 0.4848 0.3621 0.073 Uiso 1 1 calc R U . . .
C3 C 0.0913(3) 0.3939(3) 0.4669(2) 0.0629(9) Uani 1 1 d . . . . .
H3 H 0.025 0.3547 0.433 0.075 Uiso 1 1 calc R U . . .
C12 C 0.5629(3) 0.2297(3) 0.6092(3) 0.0660(9) Uani 1 1 d . . . . .
H8 H 0.5708 0.1635 0.5658 0.079 Uiso 1 1 calc R U . . .
C9 C 0.5203(3) 0.7529(4) 0.6747(3) 0.0675(10) Uani 1 1 d . . . . .
C21 C 0.2261(3) 0.5407(4) 0.9951(2) 0.0690(10) Uani 1 1 d . . . . .
H15 H 0.185 0.5896 1.0281 0.083 Uiso 1 1 calc R U . . .
C15 C 0.5388(3) 0.4207(3) 0.7344(2) 0.0638(9) Uani 1 1 d . . . . .
H11 H 0.5311 0.4856 0.7785 0.077 Uiso 1 1 calc R U . . .
C20 C 0.3018(3) 0.4471(4) 1.0373(2) 0.0700(10) Uani 1 1 d . . . . .
H14 H 0.3128 0.4298 1.0997 0.084 Uiso 1 1 calc R U . . .
C19 C 0.3625(3) 0.3770(4) 0.9900(2) 0.0708(10) Uani 1 1 d . . . . .
H13 H 0.4164 0.3129 1.02 0.085 Uiso 1 1 calc R U . . .
C13 C 0.6235(3) 0.2175(4) 0.6958(3) 0.0742(11) Uani 1 1 d . . . . .
H9 H 0.6742 0.1439 0.7126 0.089 Uiso 1 1 calc R U . . .
C14 C 0.6109(3) 0.3121(4) 0.7585(3) 0.0808(11) Uani 1 1 d . . . . .
H10 H 0.6521 0.3027 0.8191 0.097 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C16 1.232(3) . ?
N1 C16 1.354(3) . ?
N1 C1 1.433(3) . ?
N1 H1 0.88 . ?
F2 C9 1.331(4) . ?
F1 C9 1.318(4) . ?
F3 C9 1.323(4) . ?
C6 C1 1.384(3) . ?
C6 C5 1.390(4) . ?
C6 C7 1.494(4) . ?
C17 C18 1.381(4) . ?
C17 C22 1.388(4) . ?
C17 C16 1.483(4) . ?
C1 C2 1.375(4) . ?
C10 C15 1.381(4) . ?
C10 C11 1.392(4) . ?
C10 C7 1.493(4) . ?
C7 C8 1.327(4) . ?
C8 C9 1.473(4) . ?
C8 H6 0.95 . ?
C11 C12 1.384(4) . ?
C11 H7 0.95 . ?
C22 C21 1.384(4) . ?
C22 H16 0.95 . ?
C2 C3 1.377(4) . ?
C2 H2 0.95 . ?
C18 C19 1.378(4) . ?
C18 H12 0.95 . ?
C5 C4 1.371(4) . ?
C5 H5 0.95 . ?
C4 C3 1.371(4) . ?
C4 H4 0.95 . ?
C3 H3 0.95 . ?
C12 C13 1.362(5) . ?
C12 H8 0.95 . ?
C21 C20 1.358(5) . ?
C21 H15 0.95 . ?
C15 C14 1.380(5) . ?
C15 H11 0.95 . ?
C20 C19 1.377(5) . ?
C20 H14 0.95 . ?
C19 H13 0.95 . ?
C13 C14 1.371(5) . ?
C13 H9 0.95 . ?
C14 H10 0.95 . ?

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
C16 N1 C1 120.6(2) . . ?
C16 N1 H1 119.7 . . ?
C1 N1 H1 119.7 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 120.9(2) . . ?
C5 C6 C7 120.8(2) . . ?
C18 C17 C22 118.8(3) . . ?
C18 C17 C16 123.9(3) . . ?
C22 C17 C16 117.3(3) . . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 N1 119.8(2) . . ?
C6 C1 N1 119.8(2) . . ?
C15 C10 C11 118.2(3) . . ?
C15 C10 C7 122.7(3) . . ?
C11 C10 C7 119.1(3) . . ?
O1 C16 N1 121.2(3) . . ?
O1 C16 C17 121.8(2) . . ?
N1 C16 C17 117.1(2) . . ?
C8 C7 C10 126.1(3) . . ?
C8 C7 C6 119.4(3) . . ?
C10 C7 C6 114.5(2) . . ?
C7 C8 C9 127.9(3) . . ?
C7 C8 H6 116 . . ?
C9 C8 H6 116 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H7 119.8 . . ?
C10 C11 H7 119.8 . . ?
C21 C22 C17 120.2(3) . . ?
C21 C22 H16 119.9 . . ?
C17 C22 H16 119.9 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H12 119.8 . . ?
C17 C18 H12 119.8 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H8 119.7 . . ?
C11 C12 H8 119.7 . . ?
F1 C9 F3 107.0(3) . . ?
F1 C9 F2 104.3(3) . . ?
F3 C9 F2 103.8(3) . . ?
F1 C9 C8 114.2(3) . . ?
F3 C9 C8 111.6(3) . . ?
F2 C9 C8 115.0(3) . . ?
C20 C21 C22 120.3(3) . . ?
C20 C21 H15 119.8 . . ?
C22 C21 H15 119.8 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 H11 119.7 . . ?
C10 C15 H11 119.7 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H14 119.9 . . ?
C19 C20 H14 119.9 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H13 120 . . ?
C18 C19 H13 120 . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H9 120.2 . . ?
C14 C13 H9 120.2 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H10 119.7 . . ?
C15 C14 H10 119.7 . . ?

####################################################################### 
# 
# 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_SJ_AA_146
_database_code_depnum_ccdc_archive 'CCDC 1402833'
_audit_update_record             
;
2015-05-26 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_date             2015-05-20T23:57:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ?
_chemical_formula_moiety         'C22  H16  N1  O1  F3'
_chemical_formula_sum            'C22 H16 F3 N O'
_chemical_formula_weight         367.36

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   16.972(3)
_cell_length_b                   11.3201(16)
_cell_length_c                   18.722(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.676(5)
_cell_angle_gamma                90
_cell_volume                     3555.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_special_details           ?

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1793
_diffrn_reflns_number            72735
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         24.432
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.909
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             5859
_reflns_number_gt                3947
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0870P)²+6.8830P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5859
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0842
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.2066
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.191

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.63015(17) 0.5272(2) 0.33091(15) 0.0276(7) Uani 1 d . .
O1 O 0.20937(18) 0.4763(3) 0.33057(16) 0.0324(8) Uani 1 d . .
F1 F 0.44947(17) 0.5658(3) 0.34492(19) 0.0584(9) Uani 1 d . .
F4 F 0.6467(2) 0.8720(3) 0.39776(18) 0.0672(10) Uani 1 d . .
F5 F 0.7104(2) 0.7199(4) 0.44014(17) 0.0840(13) Uani 1 d . .
F3 F 0.37153(19) 0.4325(3) 0.3735(2) 0.0851(13) Uani 1 d . .
F6 F 0.5860(2) 0.7120(3) 0.4065(2) 0.0879(14) Uani 1 d . .
N1 N 0.1176(2) 0.4171(3) 0.23120(19) 0.0289(9) Uani 1 d . .
F2 F 0.3749(2) 0.4717(3) 0.2624(2) 0.0809(12) Uani 1 d . .
N2 N 0.6262(2) 0.3786(3) 0.2437(2) 0.0301(9) Uani 1 d . .
C1 C 0.1585(2) 0.4859(4) 0.1863(2) 0.0250(10) Uani 1 d . .
C16 C 0.1425(3) 0.4155(3) 0.2984(2) 0.0262(10) Uani 1 d . .
C2 C 0.1430(3) 0.4682(4) 0.1124(2) 0.0322(11) Uani 1 d . .
H1 H 0.1055 0.4098 0.0934 0.039 Uiso 1 calc . .
C28 C 0.6819(2) 0.5721(4) 0.2206(2) 0.0273(10) Uani 1 d . .
C32 C 0.7730(3) 0.5630(4) 0.3388(2) 0.0282(10) Uani 1 d . .
C23 C 0.6533(3) 0.4620(4) 0.1960(2) 0.0295(10) Uani 1 d . .
C31 C 0.6526(3) 0.7550(4) 0.3897(3) 0.0385(12) Uani 1 d . .
C38 C 0.6144(2) 0.4155(4) 0.3054(2) 0.0271(10) Uani 1 d . .
C29 C 0.6887(3) 0.5961(4) 0.3009(2) 0.0267(10) Uani 1 d . .
C17 C 0.1083(3) 0.3383(4) 0.3487(2) 0.0277(10) Uani 1 d . .
C39 C 0.5796(3) 0.3406(4) 0.3565(2) 0.0320(11) Uani 1 d . .
C7 C 0.2280(3) 0.5867(4) 0.2966(2) 0.0310(11) Uani 1 d . .
C30 C 0.6668(3) 0.7251(4) 0.3155(2) 0.0341(11) Uani 1 d . .
H22 H 0.7102 0.7764 0.3036 0.041 Uiso 1 calc . .
H21 H 0.6181 0.7455 0.2816 0.041 Uiso 1 calc . .
C3 C 0.1808(3) 0.5332(4) 0.0659(2) 0.0380(12) Uani 1 d . .
H2 H 0.1688 0.521 0.0152 0.046 Uiso 1 calc . .
C6 C 0.2154(3) 0.5709(4) 0.2148(2) 0.0302(11) Uani 1 d . .
C24 C 0.6475(3) 0.4327(4) 0.1232(2) 0.0362(11) Uani 1 d . .
H17 H 0.6269 0.3579 0.1066 0.043 Uiso 1 calc . .
C8 C 0.3146(3) 0.6143(4) 0.3296(3) 0.0342(11) Uani 1 d . .
H5 H 0.3316 0.685 0.3047 0.041 Uiso 1 calc . .
H6 H 0.3148 0.6362 0.3808 0.041 Uiso 1 calc . .
C25 C 0.6715(3) 0.5124(5) 0.0751(3) 0.0424(13) Uani 1 d . .
H18 H 0.6678 0.4923 0.0255 0.051 Uiso 1 calc . .
C27 C 0.7054(3) 0.6510(4) 0.1712(2) 0.0379(12) Uani 1 d . .
H20 H 0.7248 0.7266 0.1872 0.046 Uiso 1 calc . .
C10 C 0.1748(3) 0.6861(4) 0.3196(2) 0.0301(11) Uani 1 d . .
C20 C 0.0401(3) 0.1912(4) 0.4411(3) 0.0430(13) Uani 1 d . .
H14 H 0.0169 0.1405 0.4726 0.052 Uiso 1 calc . .
C44 C 0.5483(3) 0.2301(4) 0.3338(3) 0.0410(12) Uani 1 d . .
H32 H 0.5484 0.2048 0.2854 0.049 Uiso 1 calc . .
C33 C 0.7869(3) 0.4704(4) 0.3866(3) 0.0402(12) Uani 1 d . .
H23 H 0.743 0.4274 0.3994 0.048 Uiso 1 calc . .
C22 C 0.0457(3) 0.2641(4) 0.3215(3) 0.0377(12) Uani 1 d . .
H16 H 0.0265 0.2633 0.2711 0.045 Uiso 1 calc . .
C18 C 0.1373(3) 0.3372(4) 0.4224(3) 0.0400(12) Uani 1 d . .
H12 H 0.181 0.3863 0.4412 0.048 Uiso 1 calc . .
C26 C 0.7011(3) 0.6217(5) 0.0990(3) 0.0432(13) Uani 1 d . .
H19 H 0.7183 0.6762 0.066 0.052 Uiso 1 calc . .
C40 C 0.5777(3) 0.3759(5) 0.4273(3) 0.0424(13) Uani 1 d . .
H28 H 0.599 0.4507 0.4431 0.051 Uiso 1 calc . .
C5 C 0.2542(3) 0.6337(4) 0.1679(3) 0.0385(12) Uani 1 d . .
H4 H 0.2938 0.6896 0.1866 0.046 Uiso 1 calc . .
C4 C 0.2368(3) 0.6171(5) 0.0938(3) 0.0445(13) Uani 1 d . .
H3 H 0.2632 0.6631 0.0621 0.053 Uiso 1 calc . .
C19 C 0.1024(3) 0.2643(4) 0.4683(3) 0.0437(13) Uani 1 d . .
H13 H 0.1214 0.2647 0.5187 0.052 Uiso 1 calc . .
C21 C 0.0112(3) 0.1915(5) 0.3674(3) 0.0459(13) Uani 1 d . .
H15 H -0.0322 0.1418 0.3488 0.055 Uiso 1 calc . .
C34 C 0.8639(3) 0.4387(5) 0.4166(3) 0.0491(14) Uani 1 d . .
H24 H 0.872 0.3742 0.4493 0.059 Uiso 1 calc . .
C9 C 0.3763(3) 0.5209(4) 0.3274(3) 0.0433(13) Uani 1 d . .
C37 C 0.8387(3) 0.6251(5) 0.3229(3) 0.0426(13) Uani 1 d . .
H27 H 0.8307 0.6895 0.2901 0.051 Uiso 1 calc . .
C15 C 0.1435(4) 0.6758(5) 0.3831(3) 0.0526(15) Uani 1 d . .
H11 H 0.1521 0.6052 0.4106 0.063 Uiso 1 calc . .
C35 C 0.9282(3) 0.4995(5) 0.3994(3) 0.0510(15) Uani 1 d . .
H25 H 0.9808 0.476 0.4188 0.061 Uiso 1 calc . .
C13 C 0.0910(3) 0.8695(5) 0.3693(3) 0.0481(14) Uani 1 d . .
H9 H 0.0636 0.9337 0.3872 0.058 Uiso 1 calc . .
C42 C 0.5160(3) 0.1944(6) 0.4531(3) 0.0555(16) Uani 1 d . .
H30 H 0.4951 0.1439 0.4862 0.067 Uiso 1 calc . .
C41 C 0.5451(3) 0.3036(5) 0.4754(3) 0.0540(15) Uani 1 d . .
H29 H 0.5431 0.3296 0.5233 0.065 Uiso 1 calc . .
C43 C 0.5170(3) 0.1575(5) 0.3828(3) 0.0547(15) Uani 1 d . .
H31 H 0.4961 0.0821 0.3678 0.066 Uiso 1 calc . .
C11 C 0.1626(3) 0.7880(4) 0.2818(3) 0.0433(13) Uani 1 d . .
H7 H 0.183 0.7963 0.2376 0.052 Uiso 1 calc . .
C36 C 0.9155(3) 0.5958(6) 0.3534(3) 0.0552(16) Uani 1 d . .
H26 H 0.9593 0.6415 0.343 0.066 Uiso 1 calc . .
C14 C 0.1008(4) 0.7643(5) 0.4072(3) 0.0587(16) Uani 1 d . .
H10 H 0.0776 0.7543 0.45 0.07 Uiso 1 calc . .
C12 C 0.1207(3) 0.8802(5) 0.3067(3) 0.0498(14) Uani 1 d . .
H8 H 0.1128 0.9513 0.2797 0.06 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O2 C38 1.364(5) . ?
O2 C29 1.442(5) . ?
O1 C16 1.385(5) . ?
O1 C7 1.458(5) . ?
F1 C9 1.336(6) . ?
F4 C31 1.338(5) . ?
F5 C31 1.316(6) . ?
F3 C9 1.333(6) . ?
F6 C31 1.314(6) . ?
N1 C16 1.265(5) . ?
N1 C1 1.404(5) . ?
F2 C9 1.334(6) . ?
N2 C38 1.272(5) . ?
N2 C23 1.423(6) . ?
C1 C2 1.383(6) . ?
C1 C6 1.410(6) . ?
C16 C17 1.467(6) . ?
C2 C3 1.370(7) . ?
C2 H1 0.95 . ?
C28 C27 1.387(6) . ?
C28 C23 1.391(6) . ?
C28 C29 1.514(6) . ?
C32 C33 1.376(6) . ?
C32 C37 1.388(6) . ?
C32 C29 1.544(6) . ?
C23 C24 1.392(6) . ?
C31 C30 1.484(7) . ?
C38 C39 1.468(6) . ?
C29 C30 1.541(6) . ?
C17 C22 1.390(6) . ?
C17 C18 1.393(6) . ?
C39 C40 1.388(7) . ?
C39 C44 1.401(7) . ?
C7 C6 1.524(6) . ?
C7 C8 1.537(6) . ?
C7 C10 1.545(6) . ?
C30 H22 0.99 . ?
C30 H21 0.99 . ?
C3 C4 1.389(7) . ?
C3 H2 0.95 . ?
C6 C5 1.372(6) . ?
C24 C25 1.379(7) . ?
C24 H17 0.95 . ?
C8 C9 1.493(7) . ?
C8 H5 0.99 . ?
C8 H6 0.99 . ?
C25 C26 1.383(7) . ?
C25 H18 0.95 . ?
C27 C26 1.383(7) . ?
C27 H20 0.95 . ?
C10 C11 1.354(7) . ?
C10 C15 1.378(7) . ?
C20 C19 1.377(7) . ?
C20 C21 1.392(7) . ?
C20 H14 0.95 . ?
C44 C43 1.396(7) . ?
C44 H32 0.95 . ?
C33 C34 1.389(7) . ?
C33 H23 0.95 . ?
C22 C21 1.382(7) . ?
C22 H16 0.95 . ?
C18 C19 1.388(7) . ?
C18 H12 0.95 . ?
C26 H19 0.95 . ?
C40 C41 1.392(7) . ?
C40 H28 0.95 . ?
C5 C4 1.387(7) . ?
C5 H4 0.95 . ?
C4 H3 0.95 . ?
C19 H13 0.95 . ?
C21 H15 0.95 . ?
C34 C35 1.369(8) . ?
C34 H24 0.95 . ?
C37 C36 1.381(7) . ?
C37 H27 0.95 . ?
C15 C14 1.354(7) . ?
C15 H11 0.95 . ?
C35 C36 1.386(8) . ?
C35 H25 0.95 . ?
C13 C12 1.349(7) . ?
C13 C14 1.383(8) . ?
C13 H9 0.95 . ?
C42 C41 1.372(8) . ?
C42 C43 1.384(8) . ?
C42 H30 0.95 . ?
C41 H29 0.95 . ?
C43 H31 0.95 . ?
C11 C12 1.383(7) . ?
C11 H7 0.95 . ?
C36 H26 0.95 . ?
C14 H10 0.95 . ?
C12 H8 0.95 . ?

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
C38 O2 C29 118.3(3) . . ?
C16 O1 C7 117.0(3) . . ?
C16 N1 C1 118.8(4) . . ?
C38 N2 C23 117.5(4) . . ?
C2 C1 N1 118.9(4) . . ?
C2 C1 C6 119.5(4) . . ?
N1 C1 C6 121.6(4) . . ?
N1 C16 O1 123.7(4) . . ?
N1 C16 C17 122.8(4) . . ?
O1 C16 C17 113.2(4) . . ?
C3 C2 C1 121.4(4) . . ?
C3 C2 H1 119.3 . . ?
C1 C2 H1 119.3 . . ?
C27 C28 C23 118.5(4) . . ?
C27 C28 C29 124.1(4) . . ?
C23 C28 C29 117.4(4) . . ?
C33 C32 C37 117.4(4) . . ?
C33 C32 C29 122.7(4) . . ?
C37 C32 C29 119.9(4) . . ?
C28 C23 C24 120.5(4) . . ?
C28 C23 N2 121.1(4) . . ?
C24 C23 N2 118.3(4) . . ?
F6 C31 F5 106.9(5) . . ?
F6 C31 F4 104.9(4) . . ?
F5 C31 F4 106.1(4) . . ?
F6 C31 C30 114.0(4) . . ?
F5 C31 C30 113.3(4) . . ?
F4 C31 C30 111.0(4) . . ?
N2 C38 O2 125.0(4) . . ?
N2 C38 C39 122.4(4) . . ?
O2 C38 C39 112.6(4) . . ?
O2 C29 C28 109.7(3) . . ?
O2 C29 C30 104.1(3) . . ?
C28 C29 C30 111.2(3) . . ?
O2 C29 C32 109.6(3) . . ?
C28 C29 C32 109.8(3) . . ?
C30 C29 C32 112.3(4) . . ?
C22 C17 C18 119.6(4) . . ?
C22 C17 C16 118.6(4) . . ?
C18 C17 C16 121.8(4) . . ?
C40 C39 C44 119.0(4) . . ?
C40 C39 C38 121.7(4) . . ?
C44 C39 C38 119.3(4) . . ?
O1 C7 C6 109.3(3) . . ?
O1 C7 C8 104.8(3) . . ?
C6 C7 C8 114.1(4) . . ?
O1 C7 C10 109.1(3) . . ?
C6 C7 C10 111.5(4) . . ?
C8 C7 C10 107.7(3) . . ?
C31 C30 C29 117.4(4) . . ?
C31 C30 H22 107.9 . . ?
C29 C30 H22 107.9 . . ?
C31 C30 H21 107.9 . . ?
C29 C30 H21 107.9 . . ?
H22 C30 H21 107.2 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H2 120.4 . . ?
C4 C3 H2 120.4 . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 125.0(4) . . ?
C1 C6 C7 116.4(4) . . ?
C25 C24 C23 119.9(5) . . ?
C25 C24 H17 120.1 . . ?
C23 C24 H17 120.1 . . ?
C9 C8 C7 118.5(4) . . ?
C9 C8 H5 107.7 . . ?
C7 C8 H5 107.7 . . ?
C9 C8 H6 107.7 . . ?
C7 C8 H6 107.7 . . ?
H5 C8 H6 107.1 . . ?
C24 C25 C26 120.2(4) . . ?
C24 C25 H18 119.9 . . ?
C26 C25 H18 119.9 . . ?
C26 C27 C28 121.3(5) . . ?
C26 C27 H20 119.3 . . ?
C28 C27 H20 119.3 . . ?
C11 C10 C15 118.3(5) . . ?
C11 C10 C7 121.6(4) . . ?
C15 C10 C7 119.9(4) . . ?
C19 C20 C21 120.1(5) . . ?
C19 C20 H14 120 . . ?
C21 C20 H14 120 . . ?
C43 C44 C39 119.4(5) . . ?
C43 C44 H32 120.3 . . ?
C39 C44 H32 120.3 . . ?
C32 C33 C34 121.2(5) . . ?
C32 C33 H23 119.4 . . ?
C34 C33 H23 119.4 . . ?
C21 C22 C17 120.3(4) . . ?
C21 C22 H16 119.9 . . ?
C17 C22 H16 119.9 . . ?
C19 C18 C17 119.9(5) . . ?
C19 C18 H12 120.1 . . ?
C17 C18 H12 120.1 . . ?
C27 C26 C25 119.6(5) . . ?
C27 C26 H19 120.2 . . ?
C25 C26 H19 120.2 . . ?
C39 C40 C41 121.1(5) . . ?
C39 C40 H28 119.4 . . ?
C41 C40 H28 119.4 . . ?
C6 C5 C4 121.3(5) . . ?
C6 C5 H4 119.3 . . ?
C4 C5 H4 119.3 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H3 120.1 . . ?
C3 C4 H3 120.1 . . ?
C20 C19 C18 120.3(5) . . ?
C20 C19 H13 119.9 . . ?
C18 C19 H13 119.9 . . ?
C22 C21 C20 119.9(5) . . ?
C22 C21 H15 120.1 . . ?
C20 C21 H15 120.1 . . ?
C35 C34 C33 120.6(5) . . ?
C35 C34 H24 119.7 . . ?
C33 C34 H24 119.7 . . ?
F3 C9 F2 106.4(4) . . ?
F3 C9 F1 105.8(4) . . ?
F2 C9 F1 105.7(4) . . ?
F3 C9 C8 113.7(5) . . ?
F2 C9 C8 113.8(4) . . ?
F1 C9 C8 110.7(4) . . ?
C36 C37 C32 121.9(5) . . ?
C36 C37 H27 119 . . ?
C32 C37 H27 119 . . ?
C14 C15 C10 121.4(5) . . ?
C14 C15 H11 119.3 . . ?
C10 C15 H11 119.3 . . ?
C34 C35 C36 119.1(5) . . ?
C34 C35 H25 120.4 . . ?
C36 C35 H25 120.4 . . ?
C12 C13 C14 119.4(5) . . ?
C12 C13 H9 120.3 . . ?
C14 C13 H9 120.3 . . ?
C41 C42 C43 120.4(5) . . ?
C41 C42 H30 119.8 . . ?
C43 C42 H30 119.8 . . ?
C42 C41 C40 119.5(5) . . ?
C42 C41 H29 120.2 . . ?
C40 C41 H29 120.2 . . ?
C42 C43 C44 120.5(5) . . ?
C42 C43 H31 119.7 . . ?
C44 C43 H31 119.7 . . ?
C10 C11 C12 120.9(5) . . ?
C10 C11 H7 119.6 . . ?
C12 C11 H7 119.6 . . ?
C37 C36 C35 119.6(5) . . ?
C37 C36 H26 120.2 . . ?
C35 C36 H26 120.2 . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H10 120.2 . . ?
C13 C14 H10 120.2 . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 H8 119.9 . . ?
C11 C12 H8 119.9 . . ?



# END of CIF

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and Hexane'
