# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1575114'
_audit_update_record             
;
2017-09-17 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'methyl 4-(1-hydroxy-4-(trifluoromethyl)-1H-pyrrol-2-yl)benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 F3 N O3'
_chemical_formula_weight         285.22

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   11.243(2)
_cell_length_b                   30.552(7)
_cell_length_c                   7.3019(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2508.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9450
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   sadabs

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27221
_diffrn_reflns_av_R_equivalents  0.1196
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2208
_reflns_number_gt                1136
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0637P)²+2.0850P] 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         2208
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
O1 O 0.4863(2) 0.34034(9) 0.8222(4) 0.0682(8) Uani 1 1 d . . .
O2 O 0.3030(2) 0.34758(8) 0.9378(4) 0.0645(8) Uani 1 1 d . . .
O3 O 0.5298(2) 0.11827(9) 0.9944(4) 0.0757(9) Uani 1 1 d . . .
H3A H 0.5350 0.1314 1.0920 0.114 Uiso 1 1 calc R . .
N1 N 0.4117(3) 0.10823(10) 0.9602(4) 0.0595(9) Uani 1 1 d . . .
F1 F 0.0935(4) 0.03330(13) 0.8028(7) 0.190(2) Uani 1 1 d . . .
F2 F 0.2096(3) -0.00363(10) 0.9547(7) 0.1581(18) Uani 1 1 d . . .
F3 F 0.0900(4) 0.03589(12) 1.0841(7) 0.174(2) Uani 1 1 d . . .
C1 C 0.3675(4) 0.06722(13) 0.9714(6) 0.0691(12) Uani 1 1 d . . .
H1A H 0.4103 0.0417 0.9932 0.083 Uiso 1 1 calc R . .
C2 C 0.2476(4) 0.07058(13) 0.9445(6) 0.0634(11) Uani 1 1 d . . .
C3 C 0.2202(4) 0.11462(12) 0.9172(5) 0.0583(10) Uani 1 1 d . . .
H3B H 0.1446 0.1258 0.8955 0.070 Uiso 1 1 calc R . .
C4 C 0.3230(3) 0.13876(11) 0.9276(5) 0.0509(10) Uani 1 1 d . . .
C5 C 0.3430(3) 0.18574(11) 0.9098(5) 0.0471(9) Uani 1 1 d . . .
C6 C 0.2509(3) 0.21435(11) 0.9583(5) 0.0493(9) Uani 1 1 d . . .
H6A H 0.1788 0.2030 0.9989 0.059 Uiso 1 1 calc R . .
C7 C 0.2656(3) 0.25888(12) 0.9469(5) 0.0489(9) Uani 1 1 d . . .
H7A H 0.2037 0.2774 0.9809 0.059 Uiso 1 1 calc R . .
C8 C 0.3721(3) 0.27648(12) 0.8849(5) 0.0471(9) Uani 1 1 d . . .
C9 C 0.4625(3) 0.24832(13) 0.8313(5) 0.0510(9) Uani 1 1 d . . .
H9A H 0.5335 0.2597 0.7866 0.061 Uiso 1 1 calc R . .
C10 C 0.4481(3) 0.20354(12) 0.8435(5) 0.0519(10) Uani 1 1 d . . .
H10A H 0.5095 0.1851 0.8070 0.062 Uiso 1 1 calc R . .
C11 C 0.3936(4) 0.32382(13) 0.8765(5) 0.0520(10) Uani 1 1 d . . .
C12 C 0.3175(4) 0.39461(12) 0.9423(6) 0.0756(13) Uani 1 1 d . . .
H12A H 0.2464 0.4079 0.9895 0.113 Uiso 1 1 calc R . .
H12B H 0.3323 0.4052 0.8207 0.113 Uiso 1 1 calc R . .
H12C H 0.3835 0.4020 1.0199 0.113 Uiso 1 1 calc R . .
C13 C 0.1633(5) 0.03434(16) 0.9450(10) 0.0921(16) Uani 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
O1 C11 1.224(4) . ?
O2 C11 1.328(4) . ?
O2 C12 1.447(5) . ?
O3 N1 1.386(4) . ?
O3 H3A 0.8200 . ?
N1 C1 1.350(5) . ?
N1 C4 1.386(4) . ?
F1 C13 1.301(6) . ?
F2 C13 1.274(6) . ?
F3 C13 1.308(6) . ?
C1 C2 1.366(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.395(5) . ?
C2 C13 1.458(6) . ?
C3 C4 1.373(5) . ?
C3 H3B 0.9300 . ?
C4 C5 1.459(5) . ?
C5 C10 1.387(5) . ?
C5 C6 1.401(5) . ?
C6 C7 1.373(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.389(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.388(5) . ?
C8 C11 1.468(5) . ?
C9 C10 1.380(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C11 O2 C12 117.6(3) . . ?
N1 O3 H3A 109.5 . . ?
C1 N1 O3 123.2(3) . . ?
C1 N1 C4 111.7(3) . . ?
O3 N1 C4 124.9(3) . . ?
N1 C1 C2 106.5(4) . . ?
N1 C1 H1A 126.7 . . ?
C2 C1 H1A 126.7 . . ?
C1 C2 C3 108.1(4) . . ?
C1 C2 C13 125.8(4) . . ?
C3 C2 C13 126.1(4) . . ?
C4 C3 C2 108.9(4) . . ?
C4 C3 H3B 125.5 . . ?
C2 C3 H3B 125.5 . . ?
C3 C4 N1 104.7(3) . . ?
C3 C4 C5 130.8(3) . . ?
N1 C4 C5 124.5(3) . . ?
C10 C5 C6 118.2(3) . . ?
C10 C5 C4 123.3(3) . . ?
C6 C5 C4 118.5(3) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 C11 118.6(3) . . ?
C7 C8 C11 122.5(4) . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C10 C5 120.8(3) . . ?
C9 C10 H10A 119.6 . . ?
C5 C10 H10A 119.6 . . ?
O1 C11 O2 122.5(4) . . ?
O1 C11 C8 124.0(4) . . ?
O2 C11 C8 113.5(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F2 C13 F1 105.5(5) . . ?
F2 C13 F3 104.3(5) . . ?
F1 C13 F3 104.0(5) . . ?
F2 C13 C2 115.2(5) . . ?
F1 C13 C2 114.1(5) . . ?
F3 C13 C2 112.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane'
_chemical_properties_physical    Air-sensitive,Heat-sensitive
####################################################################### 
# 
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1575115'
_audit_update_record             
;
2017-09-17 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
4-((4-(trifluoromethyl)isoxazol-5-yl)methyl)benzonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H7 F3 N2 O'
_chemical_formula_weight         252.20

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   P2/c

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

_cell_length_a                   14.0956(5)
_cell_length_b                   11.3444(4)
_cell_length_c                   19.9859(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 134.705(2)
_cell_angle_gamma                90.00
_cell_volume                     2271.42(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9475
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26030
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4010
_reflns_number_gt                3199
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0315P)²+0.8660P] 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         4010
_refine_ls_number_parameters     379
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_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
O2 O 0.36421(11) -0.28940(9) -0.22017(7) 0.0398(3) Uani 1 1 d . . .
F4 F 0.2039(5) 0.0404(4) -0.3891(4) 0.0667(11) Uani 0.50 1 d PDU A 1
F5 F 0.2694(8) -0.0666(9) -0.4359(6) 0.089(3) Uani 0.50 1 d PDU A 1
F6 F 0.0931(4) -0.1051(4) -0.4718(3) 0.0647(13) Uani 0.50 1 d PDU A 1
F4' F 0.2637(9) 0.0445(5) -0.3716(5) 0.178(4) Uani 0.50 1 d PDU A 2
F5' F 0.2532(9) -0.0884(9) -0.4462(6) 0.080(2) Uani 0.50 1 d PDU A 2
F6' F 0.0966(6) -0.0722(7) -0.4583(5) 0.158(4) Uani 0.50 1 d PDU A 2
N3 N 0.4708(2) -0.83089(17) -0.38613(17) 0.0834(6) Uani 1 1 d . . .
N4 N 0.44407(14) -0.19166(13) -0.16295(10) 0.0462(4) Uani 1 1 d . . .
C13 C 0.4229(2) -0.75067(17) -0.38457(16) 0.0584(5) Uani 1 1 d . . .
C14 C 0.36389(17) -0.64933(15) -0.38205(12) 0.0423(4) Uani 1 1 d . . .
C15 C 0.25856(19) -0.66386(15) -0.38997(14) 0.0498(5) Uani 1 1 d . . .
H15A H 0.2251 -0.7404 -0.3972 0.060 Uiso 1 1 calc R . .
C16 C 0.20287(17) -0.56660(15) -0.38727(12) 0.0430(4) Uani 1 1 d . . .
H16A H 0.1317 -0.5768 -0.3918 0.052 Uiso 1 1 calc R . .
C17 C 0.24897(15) -0.45456(13) -0.37816(10) 0.0329(3) Uani 1 1 d . . .
C18 C 0.35408(15) -0.44108(14) -0.37058(11) 0.0350(4) Uani 1 1 d . . .
H18A H 0.3865 -0.3643 -0.3644 0.042 Uiso 1 1 calc R . .
C19 C 0.41200(16) -0.53759(15) -0.37192(11) 0.0385(4) Uani 1 1 d . . .
H19A H 0.4846 -0.5275 -0.3659 0.046 Uiso 1 1 calc R . .
C20 C 0.18148(15) -0.34840(14) -0.38119(12) 0.0387(4) Uani 1 1 d . . .
H20A H 0.1207 -0.3134 -0.4450 0.046 Uiso 1 1 calc R . .
H20B H 0.1263 -0.3747 -0.3703 0.046 Uiso 1 1 calc R . .
C21 C 0.27531(14) -0.25577(13) -0.31106(10) 0.0312(3) Uani 1 1 d . . .
C22 C 0.29385(15) -0.14057(13) -0.31554(11) 0.0336(4) Uani 1 1 d . A .
C23 C 0.40019(16) -0.10546(15) -0.22084(12) 0.0408(4) Uani 1 1 d . . .
H23A H 0.4353 -0.0277 -0.2020 0.049 Uiso 1 1 calc R . .
C24 C 0.2209(2) -0.06673(16) -0.40022(14) 0.0501(5) Uani 1 1 d D . .
O1 O -0.15060(11) -0.69624(9) -0.41865(8) 0.0397(3) Uani 1 1 d . . .
F1 F -0.3685(7) -0.4030(9) -0.4374(4) 0.097(2) Uani 0.50 1 d PDU B 1
F2 F -0.3069(7) -0.5148(4) -0.3310(5) 0.088(2) Uani 0.50 1 d PDU B 1
F3 F -0.1814(5) -0.3834(5) -0.3031(3) 0.0609(14) Uani 0.50 1 d PDU B 1
F1' F -0.3895(7) -0.4375(9) -0.4414(6) 0.122(4) Uani 0.50 1 d PDU B 2
F2' F -0.2706(8) -0.5136(6) -0.3084(5) 0.103(2) Uani 0.50 1 d PDU B 2
F3' F -0.2031(7) -0.3654(6) -0.3274(5) 0.118(3) Uani 0.50 1 d PDU B 2
N1 N 0.02246(17) -1.22381(14) -0.13168(13) 0.0582(4) Uani 1 1 d . . .
N2 N -0.07010(14) -0.60181(13) -0.40109(10) 0.0419(3) Uani 1 1 d . . .
C1 C -0.03773(18) -1.14516(15) -0.18091(14) 0.0444(4) Uani 1 1 d . . .
C2 C -0.11236(16) -1.04583(14) -0.24266(12) 0.0375(4) Uani 1 1 d . . .
C3 C -0.21577(17) -1.06227(14) -0.33921(13) 0.0412(4) Uani 1 1 d . . .
H3A H -0.2398 -1.1396 -0.3649 0.049 Uiso 1 1 calc R . .
C4 C -0.28349(16) -0.96599(14) -0.39778(12) 0.0385(4) Uani 1 1 d . . .
H4A H -0.3538 -0.9774 -0.4639 0.046 Uiso 1 1 calc R . .
C5 C -0.25007(15) -0.85285(13) -0.36117(11) 0.0336(3) Uani 1 1 d . . .
C6 C -0.14747(17) -0.83794(14) -0.26434(11) 0.0402(4) Uani 1 1 d . . .
H6A H -0.1247 -0.7608 -0.2385 0.048 Uiso 1 1 calc R . .
C7 C -0.07826(17) -0.93312(15) -0.20526(12) 0.0414(4) Uani 1 1 d . . .
H7A H -0.0075 -0.9216 -0.1392 0.050 Uiso 1 1 calc R . .
C8 C -0.32288(16) -0.74684(14) -0.42501(12) 0.0397(4) Uani 1 1 d . . .
H8A H -0.3864 -0.7733 -0.4914 0.048 Uiso 1 1 calc R . .
H8B H -0.3751 -0.7095 -0.4146 0.048 Uiso 1 1 calc R . .
C9 C -0.23072(15) -0.65780(13) -0.40865(10) 0.0327(3) Uani 1 1 d . . .
C10 C -0.20606(15) -0.54280(13) -0.38556(11) 0.0331(3) Uani 1 1 d . B .
C11 C -0.10562(16) -0.51268(15) -0.38239(11) 0.0376(4) Uani 1 1 d . . .
H11A H -0.0685 -0.4360 -0.3682 0.045 Uiso 1 1 calc R . .
C12 C -0.26730(17) -0.46327(15) -0.36613(12) 0.0434(4) Uani 1 1 d 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
O2 C21 1.3464(18) . ?
O2 N4 1.4118(17) . ?
F4 C24 1.287(4) . ?
F5 C24 1.290(5) . ?
F6 C24 1.363(4) . ?
F4' C24 1.341(6) . ?
F5' C24 1.305(6) . ?
F6' C24 1.249(6) . ?
N3 C13 1.146(2) . ?
N4 C23 1.292(2) . ?
C13 C14 1.441(2) . ?
C14 C19 1.384(2) . ?
C14 C15 1.388(2) . ?
C15 C16 1.377(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.388(2) . ?
C17 C20 1.509(2) . ?
C18 C19 1.377(2) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 C21 1.487(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.348(2) . ?
C22 C23 1.413(2) . ?
C22 C24 1.475(2) . ?
C23 H23A 0.9500 . ?
O1 C9 1.3501(18) . ?
O1 N2 1.4136(17) . ?
F1 C12 1.293(6) . ?
F2 C12 1.303(5) . ?
F3 C12 1.314(4) . ?
F1' C12 1.293(6) . ?
F2' C12 1.317(5) . ?
F3' C12 1.291(6) . ?
N1 C1 1.144(2) . ?
N2 C11 1.295(2) . ?
C1 C2 1.440(2) . ?
C2 C7 1.385(2) . ?
C2 C3 1.388(2) . ?
C3 C4 1.379(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.388(2) . ?
C5 C8 1.512(2) . ?
C6 C7 1.375(2) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 C9 1.489(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.345(2) . ?
C10 C11 1.414(2) . ?
C10 C12 1.477(2) . ?
C11 H11A 0.9500 . ?

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 N4 108.98(11) . . ?
C23 N4 O2 105.21(13) . . ?
N3 C13 C14 179.5(3) . . ?
C19 C14 C15 120.04(15) . . ?
C19 C14 C13 120.01(16) . . ?
C15 C14 C13 119.95(16) . . ?
C16 C15 C14 119.60(16) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C17 120.98(16) . . ?
C15 C16 H16A 119.5 . . ?
C17 C16 H16A 119.5 . . ?
C16 C17 C18 118.91(15) . . ?
C16 C17 C20 120.31(14) . . ?
C18 C17 C20 120.72(14) . . ?
C19 C18 C17 120.82(15) . . ?
C19 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
C18 C19 C14 119.65(15) . . ?
C18 C19 H19A 120.2 . . ?
C14 C19 H19A 120.2 . . ?
C21 C20 C17 114.11(13) . . ?
C21 C20 H20A 108.7 . . ?
C17 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C17 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
O2 C21 C22 108.93(13) . . ?
O2 C21 C20 115.98(13) . . ?
C22 C21 C20 135.08(15) . . ?
C21 C22 C23 104.89(14) . . ?
C21 C22 C24 128.00(15) . . ?
C23 C22 C24 127.11(15) . . ?
N4 C23 C22 111.99(15) . . ?
N4 C23 H23A 124.0 . . ?
C22 C23 H23A 124.0 . . ?
F6' C24 F4 84.1(5) . . ?
F6' C24 F5 115.4(6) . . ?
F4 C24 F5 109.2(5) . . ?
F6' C24 F5' 107.0(5) . . ?
F4 C24 F5' 119.9(6) . . ?
F5 C24 F5' 13.3(7) . . ?
F6' C24 F4' 111.0(5) . . ?
F4 C24 F4' 28.4(5) . . ?
F5 C24 F4' 88.9(6) . . ?
F5' C24 F4' 101.8(5) . . ?
F6' C24 F6 18.9(5) . . ?
F4 C24 F6 102.3(3) . . ?
F5 C24 F6 104.1(4) . . ?
F5' C24 F6 93.4(5) . . ?
F4' C24 F6 127.9(4) . . ?
F6' C24 C22 115.4(4) . . ?
F4 C24 C22 113.7(3) . . ?
F5 C24 C22 115.0(5) . . ?
F5' C24 C22 113.2(5) . . ?
F4' C24 C22 107.7(3) . . ?
F6 C24 C22 111.3(3) . . ?
C9 O1 N2 109.11(11) . . ?
C11 N2 O1 104.93(12) . . ?
N1 C1 C2 179.46(18) . . ?
C7 C2 C3 120.05(15) . . ?
C7 C2 C1 119.53(16) . . ?
C3 C2 C1 120.41(15) . . ?
C4 C3 C2 119.77(15) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.68(16) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 118.86(15) . . ?
C4 C5 C8 120.96(14) . . ?
C6 C5 C8 120.17(14) . . ?
C7 C6 C5 121.02(15) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C6 C7 C2 119.61(15) . . ?
C6 C7 H7A 120.2 . . ?
C2 C7 H7A 120.2 . . ?
C9 C8 C5 112.63(13) . . ?
C9 C8 H8A 109.1 . . ?
C5 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C5 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 O1 108.84(14) . . ?
C10 C9 C8 135.07(15) . . ?
O1 C9 C8 116.09(13) . . ?
C9 C10 C11 104.98(14) . . ?
C9 C10 C12 128.67(15) . . ?
C11 C10 C12 126.34(14) . . ?
N2 C11 C10 112.13(15) . . ?
N2 C11 H11A 123.9 . . ?
C10 C11 H11A 123.9 . . ?
F3' C12 F1' 107.6(6) . . ?
F3' C12 F1 88.3(6) . . ?
F1' C12 F1 20.6(9) . . ?
F3' C12 F2 116.7(5) . . ?
F1' C12 F2 90.2(6) . . ?
F1 C12 F2 105.8(5) . . ?
F3' C12 F3 17.8(5) . . ?
F1' C12 F3 122.3(6) . . ?
F1 C12 F3 104.5(5) . . ?
F2 C12 F3 104.3(4) . . ?
F3' C12 F2' 106.9(5) . . ?
F1' C12 F2' 106.1(5) . . ?
F1 C12 F2' 120.2(6) . . ?
F2 C12 F2' 16.5(6) . . ?
F3 C12 F2' 92.0(5) . . ?
F3' C12 C10 112.9(4) . . ?
F1' C12 C10 112.3(5) . . ?
F1 C12 C10 115.4(4) . . ?
F2 C12 C10 114.8(3) . . ?
F3 C12 C10 111.0(3) . . ?
F2' C12 C10 110.6(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
C21 O2 N4 C23 0.17(17) . . . . ?
N3 C13 C14 C19 35(27) . . . . ?
N3 C13 C14 C15 -145(100) . . . . ?
C19 C14 C15 C16 -0.3(3) . . . . ?
C13 C14 C15 C16 179.85(18) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C15 C16 C17 C20 176.31(16) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C20 C17 C18 C19 -177.15(15) . . . . ?
C17 C18 C19 C14 0.7(2) . . . . ?
C15 C14 C19 C18 -0.5(3) . . . . ?
C13 C14 C19 C18 179.32(17) . . . . ?
C16 C17 C20 C21 138.85(16) . . . . ?
C18 C17 C20 C21 -44.1(2) . . . . ?
N4 O2 C21 C22 0.07(16) . . . . ?
N4 O2 C21 C20 -179.17(12) . . . . ?
C17 C20 C21 O2 -59.10(19) . . . . ?
C17 C20 C21 C22 121.93(19) . . . . ?
O2 C21 C22 C23 -0.25(16) . . . . ?
C20 C21 C22 C23 178.77(16) . . . . ?
O2 C21 C22 C24 179.11(15) . . . . ?
C20 C21 C22 C24 -1.9(3) . . . . ?
O2 N4 C23 C22 -0.33(18) . . . . ?
C21 C22 C23 N4 0.38(18) . . . . ?
C24 C22 C23 N4 -178.99(16) . . . . ?
C21 C22 C24 F6' 49.7(5) . . . . ?
C23 C22 C24 F6' -131.1(5) . . . . ?
C21 C22 C24 F4 144.5(3) . . . . ?
C23 C22 C24 F4 -36.3(3) . . . . ?
C21 C22 C24 F5 -88.4(5) . . . . ?
C23 C22 C24 F5 90.8(5) . . . . ?
C21 C22 C24 F5' -74.0(5) . . . . ?
C23 C22 C24 F5' 105.2(4) . . . . ?
C21 C22 C24 F4' 174.3(4) . . . . ?
C23 C22 C24 F4' -6.5(5) . . . . ?
C21 C22 C24 F6 29.6(4) . . . . ?
C23 C22 C24 F6 -151.2(3) . . . . ?
C9 O1 N2 C11 -0.42(16) . . . . ?
N1 C1 C2 C7 -67(25) . . . . ?
N1 C1 C2 C3 112(25) . . . . ?
C7 C2 C3 C4 0.6(2) . . . . ?
C1 C2 C3 C4 -177.83(15) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C8 179.35(15) . . . . ?
C4 C5 C6 C7 1.0(2) . . . . ?
C8 C5 C6 C7 -178.67(15) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C1 C2 C7 C6 178.52(15) . . . . ?
C4 C5 C8 C9 -126.10(16) . . . . ?
C6 C5 C8 C9 53.5(2) . . . . ?
N2 O1 C9 C10 0.08(16) . . . . ?
N2 O1 C9 C8 179.88(12) . . . . ?
C5 C8 C9 C10 -122.60(19) . . . . ?
C5 C8 C9 O1 57.67(18) . . . . ?
O1 C9 C10 C11 0.27(17) . . . . ?
C8 C9 C10 C11 -179.47(16) . . . . ?
O1 C9 C10 C12 -179.04(15) . . . . ?
C8 C9 C10 C12 1.2(3) . . . . ?
O1 N2 C11 C10 0.60(17) . . . . ?
C9 C10 C11 N2 -0.56(18) . . . . ?
C12 C10 C11 N2 178.76(15) . . . . ?
C9 C10 C12 F3' 166.6(4) . . . . ?
C11 C10 C12 F3' -12.6(4) . . . . ?
C9 C10 C12 F1' -71.6(6) . . . . ?
C11 C10 C12 F1' 109.3(6) . . . . ?
C9 C10 C12 F1 -93.9(6) . . . . ?
C11 C10 C12 F1 86.9(6) . . . . ?
C9 C10 C12 F2 29.5(4) . . . . ?
C11 C10 C12 F2 -149.7(4) . . . . ?
C9 C10 C12 F3 147.5(3) . . . . ?
C11 C10 C12 F3 -31.7(4) . . . . ?
C9 C10 C12 F2' 46.8(4) . . . . ?
C11 C10 C12 F2' -132.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.031
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane'
