# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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 1012501'
_audit_update_record             
;
2014-07-07 deposited with the CCDC.
2017-06-23 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 H10 I2 O4'
_chemical_formula_weight         508.03

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'
I I -0.4742 1.8119 '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(1)/c

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                   14.884(2)
_cell_length_b                   4.3831(6)
_cell_length_c                   27.390(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.921(6)
_cell_angle_gamma                90.00
_cell_volume                     1578.9(3)
_cell_formula_units_Z            4
_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          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    3.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3613
_exptl_absorpt_correction_T_max  0.6457
_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            19434
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28.68
_reflns_number_total             3976
_reflns_number_gt                2985
_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)+(0.0223P)²+27.0941P] 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         3976
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0835
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
I1 I 0.10803(5) 0.9994(2) -0.19930(3) 0.0604(3) Uani 1 1 d . . .
I2 I 0.37071(8) 0.4008(2) 0.20819(4) 0.0748(3) Uani 1 1 d . . .
O1 O 0.1952(7) 1.153(3) -0.0760(4) 0.087(3) Uani 1 1 d . . .
O2 O 0.3307(6) 0.9583(19) -0.0045(3) 0.0532(19) Uani 1 1 d . . .
O3 O 0.3665(6) 0.735(2) 0.1093(3) 0.067(2) Uani 1 1 d . . .
O4 O 0.2411(5) 1.0154(19) 0.0456(3) 0.0529(18) Uani 1 1 d . . .
C1 C 0.3983(8) 0.669(3) -0.0659(4) 0.050(3) Uani 1 1 d . . .
H1A H 0.4359 0.6762 -0.0276 0.060 Uiso 1 1 calc R . .
C2 C 0.4359(8) 0.512(3) -0.0969(5) 0.057(3) Uani 1 1 d . . .
H2A H 0.4978 0.4103 -0.0786 0.069 Uiso 1 1 calc R . .
C3 C 0.3882(9) 0.503(3) -0.1494(6) 0.061(3) Uani 1 1 d . . .
H3A H 0.4168 0.3998 -0.1684 0.074 Uiso 1 1 calc R . .
C4 C 0.2939(9) 0.645(3) -0.1792(4) 0.057(3) Uani 1 1 d . . .
H4A H 0.2599 0.6365 -0.2176 0.068 Uiso 1 1 calc R . .
C5 C 0.2512(7) 0.802(2) -0.1500(4) 0.039(2) Uani 1 1 d . . .
C6 C 0.3036(7) 0.815(2) -0.0927(4) 0.040(2) Uani 1 1 d . . .
C7 C 0.2687(7) 0.989(3) -0.0589(4) 0.048(2) Uani 1 1 d . . .
C8 C 0.3126(10) 1.150(3) 0.0318(5) 0.058(3) Uani 1 1 d . . .
H8A H 0.3759 1.1842 0.0652 0.070 Uiso 1 1 calc R . .
H8B H 0.2872 1.3454 0.0143 0.070 Uiso 1 1 calc R . .
C9 C 0.2794(8) 0.811(3) 0.0875(4) 0.045(2) Uani 1 1 d . . .
C10 C 0.2016(8) 0.703(3) 0.1022(4) 0.051(3) Uani 1 1 d . . .
C11 C 0.2234(9) 0.538(2) 0.1491(5) 0.051(3) Uani 1 1 d . . .
C12 C 0.1458(13) 0.434(4) 0.1597(6) 0.080(4) Uani 1 1 d . . .
H12A H 0.1606 0.3127 0.1904 0.096 Uiso 1 1 calc R . .
C13 C 0.0469(15) 0.514(4) 0.1240(9) 0.104(6) Uani 1 1 d . . .
H13A H -0.0049 0.4533 0.1318 0.125 Uiso 1 1 calc R . .
C14 C 0.0240(11) 0.678(4) 0.0781(7) 0.094(5) Uani 1 1 d . . .
H14A H -0.0433 0.7281 0.0542 0.113 Uiso 1 1 calc R . .
C15 C 0.1002(9) 0.770(3) 0.0666(5) 0.068(4) Uani 1 1 d . . .
H15A H 0.0838 0.8789 0.0344 0.082 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
I1 C5 2.102(9) . ?
I2 C11 2.113(12) . ?
O1 C7 1.204(13) . ?
O2 C7 1.343(12) . ?
O2 C8 1.420(13) . ?
O3 C9 1.193(12) . ?
O4 C9 1.352(12) . ?
O4 C8 1.413(13) . ?
C1 C2 1.398(14) . ?
C1 C6 1.403(13) . ?
C1 H1A 0.9300 . ?
C2 C3 1.271(16) . ?
C2 H2A 0.9300 . ?
C3 C4 1.396(17) . ?
C3 H3A 0.9300 . ?
C4 C5 1.414(14) . ?
C4 H4A 0.9300 . ?
C5 C6 1.388(13) . ?
C6 C7 1.470(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.471(15) . ?
C10 C11 1.374(15) . ?
C10 C15 1.392(15) . ?
C11 C12 1.392(17) . ?
C12 C13 1.38(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.35(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.373(18) . ?
C14 H14A 0.9300 . ?
C15 H15A 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 O2 C8 117.4(9) . . ?
C9 O4 C8 115.6(9) . . ?
C2 C1 C6 119.8(10) . . ?
C2 C1 H1A 120.1 . . ?
C6 C1 H1A 120.1 . . ?
C3 C2 C1 122.1(10) . . ?
C3 C2 H2A 119.0 . . ?
C1 C2 H2A 119.0 . . ?
C2 C3 C4 121.7(10) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 C5 118.7(10) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
C6 C5 C4 119.8(9) . . ?
C6 C5 I1 125.0(7) . . ?
C4 C5 I1 115.2(7) . . ?
C5 C6 C1 117.9(9) . . ?
C5 C6 C7 123.8(9) . . ?
C1 C6 C7 118.2(9) . . ?
O1 C7 O2 121.3(10) . . ?
O1 C7 C6 126.1(10) . . ?
O2 C7 C6 112.6(8) . . ?
O4 C8 O2 110.8(10) . . ?
O4 C8 H8A 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O3 C9 O4 122.4(10) . . ?
O3 C9 C10 125.6(10) . . ?
O4 C9 C10 111.9(8) . . ?
C11 C10 C15 118.0(11) . . ?
C11 C10 C9 123.7(10) . . ?
C15 C10 C9 118.3(10) . . ?
C10 C11 C12 120.8(12) . . ?
C10 C11 I2 124.8(8) . . ?
C12 C11 I2 114.3(9) . . ?
C13 C12 C11 119.0(13) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C14 C13 C12 121.2(13) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C15 119.7(14) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C14 C15 C10 121.3(13) . . ?
C14 C15 H15A 119.4 . . ?
C10 C15 H15A 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.68
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.790
_refine_diff_density_min         -1.718
_refine_diff_density_rms         0.172
####################################################################### 
# 
# 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 1012812'
_audit_update_record             
;
2014-07-08 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H26 F3 N O5'
_chemical_formula_weight         477.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   14.9433(6)
_cell_length_b                   9.3141(4)
_cell_length_c                   17.6377(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.3600(10)
_cell_angle_gamma                90.00
_cell_volume                     2397.98(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(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          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9626
_exptl_absorpt_correction_T_max  0.9810
_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            27266
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4219
_reflns_number_gt                2480
_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)+(0.0613P)²+0.6153P] 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         4219
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.36946(16) 0.6005(3) 0.20830(15) 0.1535(10) Uani 1 1 d . . .
F2 F 0.29690(18) 0.4162(2) 0.16827(16) 0.1481(10) Uani 1 1 d . . .
F3 F 0.34634(15) 0.5452(2) 0.09095(12) 0.1170(8) Uani 1 1 d . . .
O1 O -0.02570(14) 0.7321(2) -0.06171(14) 0.0916(7) Uani 1 1 d . . .
O2 O 0.03042(14) 0.9380(2) -0.09564(13) 0.0902(7) Uani 1 1 d . . .
O3 O 0.11314(17) 0.5017(2) -0.15438(12) 0.0942(7) Uani 1 1 d . . .
O4 O 0.06980(13) 0.7073(2) -0.21615(11) 0.0763(6) Uani 1 1 d . . .
O5 O 0.27057(11) 0.79330(16) 0.04517(9) 0.0530(4) Uani 1 1 d . . .
N1 N 0.23316(13) 0.89701(19) -0.01385(11) 0.0513(5) Uani 1 1 d . . .
C1 C 0.29604(17) 1.0123(2) -0.01084(13) 0.0486(6) Uani 1 1 d . . .
C2 C 0.37962(19) 1.0158(3) 0.03912(16) 0.0692(8) Uani 1 1 d . . .
H2A H 0.3999 0.9359 0.0718 0.083 Uiso 1 1 calc R . .
C3 C 0.4348(2) 1.1361(3) 0.04199(18) 0.0866(10) Uani 1 1 d . . .
H3A H 0.4927 1.1383 0.0770 0.104 Uiso 1 1 calc R . .
C4 C 0.4072(2) 1.2505(3) -0.00451(17) 0.0799(9) Uani 1 1 d . . .
H4A H 0.4455 1.3325 -0.0020 0.096 Uiso 1 1 calc R . .
C5 C 0.3243(2) 1.2473(3) -0.05494(18) 0.0773(9) Uani 1 1 d . . .
H5A H 0.3051 1.3270 -0.0881 0.093 Uiso 1 1 calc R . .
C6 C 0.2680(2) 1.1293(3) -0.05817(16) 0.0679(8) Uani 1 1 d . . .
H6A H 0.2099 1.1283 -0.0930 0.081 Uiso 1 1 calc R . .
C7 C 0.27800(16) 0.7577(2) -0.12567(14) 0.0496(6) Uani 1 1 d . . .
C8 C 0.33780(18) 0.6516(3) -0.09106(15) 0.0586(7) Uani 1 1 d . . .
H8A H 0.3366 0.6212 -0.0399 0.070 Uiso 1 1 calc R . .
C9 C 0.3992(2) 0.5890(3) -0.12955(17) 0.0677(8) Uani 1 1 d . . .
H9A H 0.4392 0.5157 -0.1047 0.081 Uiso 1 1 calc R . .
C10 C 0.4030(2) 0.6317(3) -0.20330(18) 0.0718(8) Uani 1 1 d . . .
H10A H 0.4445 0.5875 -0.2300 0.086 Uiso 1 1 calc R . .
C11 C 0.3459(2) 0.7391(4) -0.23765(17) 0.0788(9) Uani 1 1 d . . .
H11A H 0.3487 0.7708 -0.2883 0.095 Uiso 1 1 calc R . .
C12 C 0.2841(2) 0.8018(3) -0.19951(15) 0.0668(8) Uani 1 1 d . . .
H12A H 0.2452 0.8764 -0.2243 0.080 Uiso 1 1 calc R . .
C13 C 0.20428(17) 0.8255(3) -0.08996(14) 0.0527(6) Uani 1 1 d . . .
H13A H 0.1756 0.9021 -0.1270 0.063 Uiso 1 1 calc R . .
C14 C 0.12491(16) 0.7221(3) -0.08164(14) 0.0550(6) Uani 1 1 d . . .
C15 C 0.15095(18) 0.6279(3) -0.00886(14) 0.0578(7) Uani 1 1 d . . .
H15A H 0.0957 0.5782 0.0005 0.069 Uiso 1 1 calc R . .
H15B H 0.1956 0.5540 -0.0170 0.069 Uiso 1 1 calc R . .
C16 C 0.19256(18) 0.7188(3) 0.06143(14) 0.0550(6) Uani 1 1 d . . .
H16A H 0.1461 0.7923 0.0683 0.066 Uiso 1 1 calc R . .
C17 C 0.1873(3) 0.5493(4) 0.2634(2) 0.1171(14) Uani 1 1 d . . .
H17A H 0.2465 0.5006 0.2685 0.176 Uiso 1 1 calc R . .
H17B H 0.1391 0.4779 0.2632 0.176 Uiso 1 1 calc R . .
H17C H 0.1900 0.6151 0.3072 0.176 Uiso 1 1 calc R . .
C18 C 0.1663(2) 0.6334(3) 0.18810(17) 0.0760(9) Uani 1 1 d . . .
C19 C 0.0774(3) 0.7132(4) 0.1766(2) 0.1065(12) Uani 1 1 d . . .
H19A H 0.0860 0.8113 0.1593 0.160 Uiso 1 1 calc R . .
H19B H 0.0568 0.7165 0.2257 0.160 Uiso 1 1 calc R . .
H19C H 0.0313 0.6642 0.1372 0.160 Uiso 1 1 calc R . .
C20 C 0.21981(19) 0.6360(3) 0.13646(15) 0.0608(7) Uani 1 1 d . . .
C21 C 0.3063(2) 0.5531(4) 0.15053(19) 0.0808(9) Uani 1 1 d . . .
C22 C 0.0393(2) 0.8140(3) -0.08055(17) 0.0674(8) Uani 1 1 d . . .
C23 C -0.1117(2) 0.8036(4) -0.0604(3) 0.1335(16) Uani 1 1 d . . .
H23A H -0.1546 0.7345 -0.0459 0.200 Uiso 1 1 calc R . .
H23B H -0.1378 0.8428 -0.1119 0.200 Uiso 1 1 calc R . .
H23C H -0.1008 0.8818 -0.0223 0.200 Uiso 1 1 calc R . .
C24 C 0.10203(18) 0.6280(3) -0.15357(17) 0.0641(7) Uani 1 1 d . . .
C25 C 0.0535(3) 0.6350(4) -0.29073(17) 0.1013(12) Uani 1 1 d . . .
H25A H 0.0306 0.7043 -0.3321 0.152 Uiso 1 1 calc R . .
H25B H 0.0080 0.5588 -0.2917 0.152 Uiso 1 1 calc R . .
H25C H 0.1109 0.5929 -0.2987 0.152 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 C21 1.309(4) . ?
F2 C21 1.327(4) . ?
F3 C21 1.318(3) . ?
O1 C22 1.332(3) . ?
O1 C23 1.452(4) . ?
O2 C22 1.186(3) . ?
O3 C24 1.189(3) . ?
O4 C24 1.330(3) . ?
O4 C25 1.451(3) . ?
O5 C16 1.437(3) . ?
O5 N1 1.442(2) . ?
N1 C1 1.421(3) . ?
N1 C13 1.478(3) . ?
C1 C2 1.366(3) . ?
C1 C6 1.382(3) . ?
C2 C3 1.385(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.354(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.362(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.378(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(3) . ?
C7 C12 1.387(3) . ?
C7 C13 1.519(3) . ?
C8 C9 1.382(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.373(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.369(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.383(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.559(3) . ?
C13 H13A 1.0000 . ?
C14 C24 1.520(4) . ?
C14 C15 1.535(3) . ?
C14 C22 1.543(4) . ?
C15 C16 1.520(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C20 1.510(3) . ?
C16 H16A 1.0000 . ?
C17 C18 1.516(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.334(4) . ?
C18 C19 1.498(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.481(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C22 O1 C23 115.9(3) . . ?
C24 O4 C25 117.1(2) . . ?
C16 O5 N1 105.17(16) . . ?
C1 N1 O5 109.17(16) . . ?
C1 N1 C13 115.90(19) . . ?
O5 N1 C13 110.28(16) . . ?
C2 C1 C6 119.2(2) . . ?
C2 C1 N1 123.2(2) . . ?
C6 C1 N1 117.5(2) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
C8 C7 C12 117.4(2) . . ?
C8 C7 C13 124.8(2) . . ?
C12 C7 C13 117.7(2) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10A 120.6 . . ?
C9 C10 H10A 120.6 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C11 C12 C7 121.1(3) . . ?
C11 C12 H12A 119.5 . . ?
C7 C12 H12A 119.5 . . ?
N1 C13 C7 117.87(19) . . ?
N1 C13 C14 105.83(19) . . ?
C7 C13 C14 114.60(19) . . ?
N1 C13 H13A 105.9 . . ?
C7 C13 H13A 105.9 . . ?
C14 C13 H13A 105.9 . . ?
C24 C14 C15 109.9(2) . . ?
C24 C14 C22 106.9(2) . . ?
C15 C14 C22 111.7(2) . . ?
C24 C14 C13 108.5(2) . . ?
C15 C14 C13 111.73(19) . . ?
C22 C14 C13 107.9(2) . . ?
C16 C15 C14 110.46(19) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
O5 C16 C20 110.1(2) . . ?
O5 C16 C15 108.28(19) . . ?
C20 C16 C15 114.6(2) . . ?
O5 C16 H16A 107.9 . . ?
C20 C16 H16A 107.9 . . ?
C15 C16 H16A 107.9 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C18 C19 122.8(3) . . ?
C20 C18 C17 124.5(3) . . ?
C19 C18 C17 112.7(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 120.3(3) . . ?
C18 C20 C16 121.3(3) . . ?
C21 C20 C16 118.4(2) . . ?
F1 C21 F3 105.4(3) . . ?
F1 C21 F2 103.6(3) . . ?
F3 C21 F2 102.9(3) . . ?
F1 C21 C20 114.4(3) . . ?
F3 C21 C20 115.1(3) . . ?
F2 C21 C20 114.1(3) . . ?
O2 C22 O1 124.1(3) . . ?
O2 C22 C14 126.2(3) . . ?
O1 C22 C14 109.6(3) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 O4 124.5(3) . . ?
O3 C24 C14 125.0(3) . . ?
O4 C24 C14 110.5(2) . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 O5 N1 C1 155.54(18) . . . . ?
C16 O5 N1 C13 -76.0(2) . . . . ?
O5 N1 C1 C2 2.6(3) . . . . ?
C13 N1 C1 C2 -122.7(3) . . . . ?
O5 N1 C1 C6 -173.8(2) . . . . ?
C13 N1 C1 C6 61.0(3) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
N1 C1 C2 C3 -176.0(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
N1 C1 C6 C5 176.8(3) . . . . ?
C12 C7 C8 C9 -2.0(4) . . . . ?
C13 C7 C8 C9 175.8(2) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C8 C7 C12 C11 1.8(4) . . . . ?
C13 C7 C12 C11 -176.2(2) . . . . ?
C1 N1 C13 C7 59.2(3) . . . . ?
O5 N1 C13 C7 -65.4(2) . . . . ?
C1 N1 C13 C14 -171.03(19) . . . . ?
O5 N1 C13 C14 64.3(2) . . . . ?
C8 C7 C13 N1 58.3(3) . . . . ?
C12 C7 C13 N1 -123.9(2) . . . . ?
C8 C7 C13 C14 -67.3(3) . . . . ?
C12 C7 C13 C14 110.5(2) . . . . ?
N1 C13 C14 C24 -171.2(2) . . . . ?
C7 C13 C14 C24 -39.6(3) . . . . ?
N1 C13 C14 C15 -49.9(3) . . . . ?
C7 C13 C14 C15 81.7(3) . . . . ?
N1 C13 C14 C22 73.3(2) . . . . ?
C7 C13 C14 C22 -155.1(2) . . . . ?
C24 C14 C15 C16 168.4(2) . . . . ?
C22 C14 C15 C16 -73.1(3) . . . . ?
C13 C14 C15 C16 47.9(3) . . . . ?
N1 O5 C16 C20 -164.78(18) . . . . ?
N1 O5 C16 C15 69.2(2) . . . . ?
C14 C15 C16 O5 -57.2(3) . . . . ?
C14 C15 C16 C20 179.5(2) . . . . ?
C19 C18 C20 C21 -179.1(3) . . . . ?
C17 C18 C20 C21 0.1(4) . . . . ?
C19 C18 C20 C16 -1.2(4) . . . . ?
C17 C18 C20 C16 178.0(3) . . . . ?
O5 C16 C20 C18 138.0(2) . . . . ?
C15 C16 C20 C18 -99.6(3) . . . . ?
O5 C16 C20 C21 -44.0(3) . . . . ?
C15 C16 C20 C21 78.3(3) . . . . ?
C18 C20 C21 F1 -67.9(4) . . . . ?
C16 C20 C21 F1 114.2(3) . . . . ?
C18 C20 C21 F3 169.9(3) . . . . ?
C16 C20 C21 F3 -8.1(4) . . . . ?
C18 C20 C21 F2 51.2(4) . . . . ?
C16 C20 C21 F2 -126.8(3) . . . . ?
C23 O1 C22 O2 0.0(5) . . . . ?
C23 O1 C22 C14 -178.4(3) . . . . ?
C24 C14 C22 O2 -105.6(3) . . . . ?
C15 C14 C22 O2 134.2(3) . . . . ?
C13 C14 C22 O2 11.0(4) . . . . ?
C24 C14 C22 O1 72.8(3) . . . . ?
C15 C14 C22 O1 -47.4(3) . . . . ?
C13 C14 C22 O1 -170.6(2) . . . . ?
C25 O4 C24 O3 -4.6(4) . . . . ?
C25 O4 C24 C14 173.9(2) . . . . ?
C15 C14 C24 O3 -8.3(4) . . . . ?
C22 C14 C24 O3 -129.7(3) . . . . ?
C13 C14 C24 O3 114.1(3) . . . . ?
C15 C14 C24 O4 173.2(2) . . . . ?
C22 C14 C24 O4 51.8(3) . . . . ?
C13 C14 C24 O4 -64.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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 1012813'
_audit_update_record             
;
2014-07-08 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 F3 N O4'
_chemical_formula_weight         411.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   15.6855(6)
_cell_length_b                   9.6366(3)
_cell_length_c                   13.4345(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.4000(10)
_cell_angle_gamma                90.00
_cell_volume                     2018.03(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(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          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_T_max  0.9824
_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            23009
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3551
_reflns_number_gt                2639
_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)+(0.0493P)²+0.9471P] 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         3551
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.73096(9) -0.06210(13) -0.02641(11) 0.0554(4) Uani 1 1 d . . .
F2 F 0.63512(8) 0.06494(14) 0.03008(9) 0.0472(4) Uani 1 1 d . . .
F3 F 0.76683(8) 0.11970(14) 0.05916(9) 0.0465(4) Uani 1 1 d . . .
O1 O 0.63206(12) 0.5650(2) -0.24465(13) 0.0655(6) Uani 1 1 d . . .
O2 O 0.74901(11) 0.64335(17) -0.15580(12) 0.0526(5) Uani 1 1 d . . .
O3 O 0.68181(12) 0.57717(18) 0.08790(12) 0.0575(5) Uani 1 1 d . . .
O4 O 0.57597(10) 0.64567(16) -0.02478(11) 0.0437(4) Uani 1 1 d . . .
N1 N 0.99520(11) 0.19291(19) -0.03998(14) 0.0389(5) Uani 1 1 d . . .
C1 C 0.89645(13) 0.1347(2) -0.16762(15) 0.0298(5) Uani 1 1 d . . .
C2 C 0.86800(15) 0.0687(2) -0.25794(16) 0.0362(5) Uani 1 1 d . . .
H2A H 0.8102 0.0782 -0.2869 0.043 Uiso 1 1 calc R . .
C3 C 0.92520(17) -0.0105(2) -0.30432(19) 0.0480(6) Uani 1 1 d . . .
H3A H 0.9064 -0.0555 -0.3658 0.058 Uiso 1 1 calc R . .
C4 C 1.01026(18) -0.0256(3) -0.2626(2) 0.0542(7) Uani 1 1 d . . .
H4A H 1.0481 -0.0812 -0.2961 0.065 Uiso 1 1 calc R . .
C5 C 1.04071(16) 0.0383(2) -0.1740(2) 0.0473(6) Uani 1 1 d . . .
H5A H 1.0986 0.0277 -0.1457 0.057 Uiso 1 1 calc R . .
C6 C 0.98316(14) 0.1188(2) -0.12761(16) 0.0350(5) Uani 1 1 d . . .
C7 C 0.91906(13) 0.2541(2) -0.02410(16) 0.0354(5) Uani 1 1 d . . .
H7A H 0.9108 0.3107 0.0319 0.042 Uiso 1 1 calc R . .
C8 C 0.85673(13) 0.2224(2) -0.09985(15) 0.0290(5) Uani 1 1 d . . .
C9 C 0.76494(12) 0.2727(2) -0.11367(14) 0.0283(5) Uani 1 1 d . . .
H9A H 0.7548 0.3104 -0.1833 0.034 Uiso 1 1 calc R . .
C10 C 0.75070(13) 0.3947(2) -0.04290(15) 0.0323(5) Uani 1 1 d . . .
H10A H 0.7459 0.3578 0.0250 0.039 Uiso 1 1 calc R . .
H10B H 0.8013 0.4568 -0.0386 0.039 Uiso 1 1 calc R . .
C11 C 0.67039(13) 0.4786(2) -0.07750(15) 0.0304(5) Uani 1 1 d . . .
H11A H 0.6223 0.4117 -0.0951 0.036 Uiso 1 1 calc R . .
C12 C 0.68010(14) 0.5656(2) -0.16958(16) 0.0330(5) Uani 1 1 d . . .
C13 C 0.76521(18) 0.7335(3) -0.2380(2) 0.0631(8) Uani 1 1 d . . .
H13A H 0.8180 0.7863 -0.2195 0.095 Uiso 1 1 calc R . .
H13B H 0.7170 0.7977 -0.2525 0.095 Uiso 1 1 calc R . .
H13C H 0.7716 0.6773 -0.2975 0.095 Uiso 1 1 calc R . .
C14 C 0.64532(14) 0.5719(2) 0.00549(16) 0.0328(5) Uani 1 1 d . . .
C15 C 0.54644(16) 0.7382(2) 0.04866(19) 0.0486(6) Uani 1 1 d . . .
H15A H 0.4953 0.7878 0.0189 0.073 Uiso 1 1 calc R . .
H15B H 0.5917 0.8052 0.0704 0.073 Uiso 1 1 calc R . .
H15C H 0.5322 0.6844 0.1065 0.073 Uiso 1 1 calc R . .
C16 C 0.70027(13) 0.1553(2) -0.10765(15) 0.0295(5) Uani 1 1 d . . .
C17 C 0.70872(14) 0.0711(2) -0.01280(17) 0.0352(5) Uani 1 1 d . . .
C18 C 0.63821(13) 0.1221(2) -0.18077(16) 0.0344(5) Uani 1 1 d . . .
C19 C 0.62080(15) 0.2031(3) -0.27690(16) 0.0458(6) Uani 1 1 d . . .
H19A H 0.6605 0.2817 -0.2758 0.069 Uiso 1 1 calc R . .
H19B H 0.5617 0.2376 -0.2836 0.069 Uiso 1 1 calc R . .
H19C H 0.6289 0.1427 -0.3338 0.069 Uiso 1 1 calc R . .
C20 C 0.57877(15) -0.0009(2) -0.1779(2) 0.0482(6) Uani 1 1 d . . .
H20A H 0.5919 -0.0504 -0.1144 0.072 Uiso 1 1 calc R . .
H20B H 0.5866 -0.0635 -0.2337 0.072 Uiso 1 1 calc R . .
H20C H 0.5192 0.0316 -0.1840 0.072 Uiso 1 1 calc R . .
C21 C 1.07530(14) 0.2052(3) 0.0259(2) 0.0519(7) Uani 1 1 d . . .
H21A H 1.0662 0.2644 0.0832 0.078 Uiso 1 1 calc R . .
H21B H 1.1193 0.2467 -0.0111 0.078 Uiso 1 1 calc R . .
H21C H 1.0941 0.1130 0.0500 0.078 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.348(2) . ?
F2 C17 1.348(2) . ?
F3 C17 1.337(2) . ?
O1 C12 1.190(2) . ?
O2 C12 1.311(3) . ?
O2 C13 1.449(3) . ?
O3 C14 1.189(2) . ?
O4 C14 1.325(2) . ?
O4 C15 1.444(3) . ?
N1 C7 1.370(3) . ?
N1 C6 1.372(3) . ?
N1 C21 1.459(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.414(3) . ?
C1 C8 1.434(3) . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.396(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5A 0.9500 . ?
C7 C8 1.365(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.511(3) . ?
C9 C16 1.528(3) . ?
C9 C10 1.543(3) . ?
C9 H9A 1.0000 . ?
C10 C11 1.525(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.516(3) . ?
C11 C14 1.518(3) . ?
C11 H11A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.342(3) . ?
C16 C17 1.504(3) . ?
C18 C19 1.508(3) . ?
C18 C20 1.511(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C12 O2 C13 116.52(18) . . ?
C14 O4 C15 115.89(17) . . ?
C7 N1 C6 108.57(17) . . ?
C7 N1 C21 125.3(2) . . ?
C6 N1 C21 126.2(2) . . ?
C2 C1 C6 118.75(19) . . ?
C2 C1 C8 134.40(19) . . ?
C6 C1 C8 106.85(18) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
C4 C5 C6 117.2(2) . . ?
C4 C5 H5A 121.4 . . ?
C6 C5 H5A 121.4 . . ?
N1 C6 C5 129.9(2) . . ?
N1 C6 C1 107.73(18) . . ?
C5 C6 C1 122.4(2) . . ?
C8 C7 N1 110.61(19) . . ?
C8 C7 H7A 124.7 . . ?
N1 C7 H7A 124.7 . . ?
C7 C8 C1 106.23(18) . . ?
C7 C8 C9 127.81(18) . . ?
C1 C8 C9 125.91(18) . . ?
C8 C9 C16 112.62(16) . . ?
C8 C9 C10 111.73(16) . . ?
C16 C9 C10 112.88(16) . . ?
C8 C9 H9A 106.3 . . ?
C16 C9 H9A 106.3 . . ?
C10 C9 H9A 106.3 . . ?
C11 C10 C9 112.80(16) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C14 109.27(16) . . ?
C12 C11 C10 112.78(17) . . ?
C14 C11 C10 111.29(16) . . ?
C12 C11 H11A 107.8 . . ?
C14 C11 H11A 107.8 . . ?
C10 C11 H11A 107.8 . . ?
O1 C12 O2 123.8(2) . . ?
O1 C12 C11 125.3(2) . . ?
O2 C12 C11 110.91(17) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O4 123.8(2) . . ?
O3 C14 C11 124.88(19) . . ?
O4 C14 C11 111.31(18) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C17 118.66(19) . . ?
C18 C16 C9 124.71(18) . . ?
C17 C16 C9 116.62(17) . . ?
F3 C17 F2 104.70(17) . . ?
F3 C17 F1 105.40(17) . . ?
F2 C17 F1 105.24(17) . . ?
F3 C17 C16 114.35(17) . . ?
F2 C17 C16 112.78(17) . . ?
F1 C17 C16 113.48(18) . . ?
C16 C18 C19 123.4(2) . . ?
C16 C18 C20 124.6(2) . . ?
C19 C18 C20 111.98(19) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(3) . . . . ?
C8 C1 C2 C3 -179.8(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C7 N1 C6 C5 -179.0(2) . . . . ?
C21 N1 C6 C5 1.0(4) . . . . ?
C7 N1 C6 C1 0.1(2) . . . . ?
C21 N1 C6 C1 -180.0(2) . . . . ?
C4 C5 C6 N1 179.7(2) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C2 C1 C6 N1 179.82(18) . . . . ?
C8 C1 C6 N1 0.1(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C8 C1 C6 C5 179.27(19) . . . . ?
C6 N1 C7 C8 -0.2(2) . . . . ?
C21 N1 C7 C8 179.8(2) . . . . ?
N1 C7 C8 C1 0.3(2) . . . . ?
N1 C7 C8 C9 -177.38(19) . . . . ?
C2 C1 C8 C7 -179.9(2) . . . . ?
C6 C1 C8 C7 -0.3(2) . . . . ?
C2 C1 C8 C9 -2.1(4) . . . . ?
C6 C1 C8 C9 177.48(18) . . . . ?
C7 C8 C9 C16 -115.6(2) . . . . ?
C1 C8 C9 C16 67.1(3) . . . . ?
C7 C8 C9 C10 12.7(3) . . . . ?
C1 C8 C9 C10 -164.57(18) . . . . ?
C8 C9 C10 C11 160.54(17) . . . . ?
C16 C9 C10 C11 -71.3(2) . . . . ?
C9 C10 C11 C12 -71.7(2) . . . . ?
C9 C10 C11 C14 165.06(17) . . . . ?
C13 O2 C12 O1 0.6(3) . . . . ?
C13 O2 C12 C11 -179.1(2) . . . . ?
C14 C11 C12 O1 -108.4(2) . . . . ?
C10 C11 C12 O1 127.2(2) . . . . ?
C14 C11 C12 O2 71.3(2) . . . . ?
C10 C11 C12 O2 -53.0(2) . . . . ?
C15 O4 C14 O3 1.2(3) . . . . ?
C15 O4 C14 C11 179.97(18) . . . . ?
C12 C11 C14 O3 -127.0(2) . . . . ?
C10 C11 C14 O3 -1.8(3) . . . . ?
C12 C11 C14 O4 54.3(2) . . . . ?
C10 C11 C14 O4 179.50(17) . . . . ?
C8 C9 C16 C18 -121.6(2) . . . . ?
C10 C9 C16 C18 110.7(2) . . . . ?
C8 C9 C16 C17 57.6(2) . . . . ?
C10 C9 C16 C17 -70.1(2) . . . . ?
C18 C16 C17 F3 -174.02(18) . . . . ?
C9 C16 C17 F3 6.7(2) . . . . ?
C18 C16 C17 F2 -54.5(2) . . . . ?
C9 C16 C17 F2 126.23(19) . . . . ?
C18 C16 C17 F1 65.0(2) . . . . ?
C9 C16 C17 F1 -114.21(19) . . . . ?
C17 C16 C18 C19 176.90(19) . . . . ?
C9 C16 C18 C19 -3.9(3) . . . . ?
C17 C16 C18 C20 -4.2(3) . . . . ?
C9 C16 C18 C20 175.00(19) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.219
_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_z
_database_code_depnum_ccdc_archive 'CCDC 1012706'
_audit_update_record             
;
2014-07-08 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 F3 O5'
_chemical_formula_weight         386.36

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'
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                   8.5770(4)
_cell_length_b                   11.2530(5)
_cell_length_c                   11.3999(5)
_cell_angle_alpha                83.2610(10)
_cell_angle_beta                 69.7150(10)
_cell_angle_gamma                68.4110(10)
_cell_volume                     959.58(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(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          0.52
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9429
_exptl_absorpt_correction_T_max  0.9842
_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            11222
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3370
_reflns_number_gt                2628
_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)+(0.0991P)²+0.3868P] 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         3370
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1907
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.5187(3) 0.5632(2) 0.2993(2) 0.0835(7) Uani 1 1 d . . .
O2 O 0.2587(3) 0.55053(16) 0.42195(18) 0.0664(5) Uani 1 1 d . . .
O3 O 0.2197(3) 0.7230(2) 0.60973(16) 0.0730(6) Uani 1 1 d . . .
O4 O -0.0126(3) 0.8324(2) 0.5476(2) 0.0928(8) Uani 1 1 d . . .
O5 O 0.3158(2) 0.87566(15) 0.20842(15) 0.0501(4) Uani 1 1 d . . .
F1 F 0.5342(5) 1.1737(2) 0.2079(2) 0.1377(11) Uani 1 1 d . . .
F2 F 0.7031(3) 1.0391(3) 0.2941(3) 0.1222(9) Uani 1 1 d . . .
F3 F 0.4308(3) 1.1002(2) 0.38582(19) 0.1027(7) Uani 1 1 d . . .
C1 C -0.0014(4) 0.7089(3) 0.2761(3) 0.0702(8) Uani 1 1 d . . .
H1A H -0.0860 0.7505 0.3519 0.084 Uiso 1 1 calc R . .
C2 C -0.0325(5) 0.6218(3) 0.2212(4) 0.0880(10) Uani 1 1 d . . .
H2A H -0.1374 0.6020 0.2597 0.106 Uiso 1 1 calc R . .
C3 C 0.0874(6) 0.5633(4) 0.1110(4) 0.0931(11) Uani 1 1 d . . .
H3A H 0.0663 0.5020 0.0738 0.112 Uiso 1 1 calc R . .
C4 C 0.2377(5) 0.5928(3) 0.0538(3) 0.0873(10) Uani 1 1 d . . .
H4A H 0.3190 0.5536 -0.0239 0.105 Uiso 1 1 calc R . .
C5 C 0.2714(4) 0.6798(3) 0.1095(3) 0.0691(8) Uani 1 1 d . . .
H5A H 0.3758 0.7000 0.0701 0.083 Uiso 1 1 calc R . .
C6 C 0.1534(3) 0.7369(2) 0.2217(2) 0.0541(6) Uani 1 1 d . . .
C7 C 0.1933(3) 0.8222(2) 0.2913(2) 0.0479(6) Uani 1 1 d . . .
H7A H 0.0803 0.8934 0.3318 0.057 Uiso 1 1 calc R . .
C8 C 0.3793(3) 0.9241(2) 0.2860(2) 0.0494(6) Uani 1 1 d . . .
H8A H 0.2813 1.0012 0.3321 0.059 Uiso 1 1 calc R . .
C9 C 0.4153(3) 0.8185(3) 0.3800(2) 0.0565(6) Uani 1 1 d . . .
H9A H 0.3975 0.8544 0.4608 0.068 Uiso 1 1 calc R . .
H9B H 0.5381 0.7567 0.3480 0.068 Uiso 1 1 calc R . .
C10 C 0.2792(3) 0.7542(2) 0.3949(2) 0.0455(5) Uani 1 1 d . . .
C11 C 0.3702(3) 0.6124(2) 0.3669(2) 0.0534(6) Uani 1 1 d . . .
C12 C 0.3196(6) 0.4168(3) 0.3897(4) 0.0989(12) Uani 1 1 d . . .
H12A H 0.2267 0.3817 0.4357 0.148 Uiso 1 1 calc R . .
H12B H 0.4269 0.3703 0.4119 0.148 Uiso 1 1 calc R . .
H12C H 0.3465 0.4079 0.2996 0.148 Uiso 1 1 calc R . .
C13 C 0.1420(3) 0.7760(2) 0.5246(2) 0.0557(6) Uani 1 1 d . . .
C14 C 0.1061(6) 0.7311(4) 0.7378(3) 0.1027(13) Uani 1 1 d . . .
H14A H 0.1783 0.6889 0.7915 0.154 Uiso 1 1 calc R . .
H14B H 0.0212 0.6890 0.7463 0.154 Uiso 1 1 calc R . .
H14C H 0.0416 0.8212 0.7631 0.154 Uiso 1 1 calc R . .
C15 C 0.8187(4) 0.9517(3) 0.0376(3) 0.0760(9) Uani 1 1 d . . .
H15A H 0.8089 1.0255 0.0813 0.114 Uiso 1 1 calc R . .
H15B H 0.8172 0.9761 -0.0475 0.114 Uiso 1 1 calc R . .
H15C H 0.9303 0.8820 0.0339 0.114 Uiso 1 1 calc R . .
C16 C 0.6644(3) 0.9081(2) 0.1071(2) 0.0543(6) Uani 1 1 d . . .
C17 C 0.6715(4) 0.7959(3) 0.0439(3) 0.0709(8) Uani 1 1 d . . .
H17A H 0.5698 0.7702 0.0919 0.106 Uiso 1 1 calc R . .
H17B H 0.7819 0.7245 0.0393 0.106 Uiso 1 1 calc R . .
H17C H 0.6673 0.8195 -0.0408 0.106 Uiso 1 1 calc R . .
C18 C 0.5376(3) 0.9623(2) 0.2120(2) 0.0507(6) Uani 1 1 d . . .
C19 C 0.5479(4) 1.0687(3) 0.2726(3) 0.0705(8) 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 1.193(3) . ?
O2 C11 1.328(3) . ?
O2 C12 1.446(3) . ?
O3 C13 1.327(3) . ?
O3 C14 1.439(3) . ?
O4 C13 1.186(3) . ?
O5 C7 1.415(3) . ?
O5 C8 1.429(3) . ?
F1 C19 1.307(4) . ?
F2 C19 1.350(4) . ?
F3 C19 1.322(3) . ?
C1 C2 1.370(4) . ?
C1 C6 1.392(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.367(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.371(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.375(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.509(3) . ?
C7 C10 1.581(3) . ?
C7 H7A 1.0000 . ?
C8 C18 1.513(3) . ?
C8 C9 1.522(4) . ?
C8 H8A 1.0000 . ?
C9 C10 1.540(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.512(3) . ?
C10 C13 1.516(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.510(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.330(3) . ?
C16 C17 1.498(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.494(4) . ?

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 116.9(2) . . ?
C13 O3 C14 117.0(3) . . ?
C7 O5 C8 105.57(17) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 121.6(2) . . ?
C1 C6 C7 119.2(2) . . ?
O5 C7 C6 110.88(19) . . ?
O5 C7 C10 104.96(17) . . ?
C6 C7 C10 115.41(19) . . ?
O5 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C10 C7 H7A 108.5 . . ?
O5 C8 C18 112.72(19) . . ?
O5 C8 C9 104.19(19) . . ?
C18 C8 C9 114.5(2) . . ?
O5 C8 H8A 108.4 . . ?
C18 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C8 C9 C10 104.36(19) . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C11 C10 C13 109.79(19) . . ?
C11 C10 C9 111.1(2) . . ?
C13 C10 C9 111.80(19) . . ?
C11 C10 C7 109.86(18) . . ?
C13 C10 C7 111.71(19) . . ?
C9 C10 C7 102.40(18) . . ?
O1 C11 O2 124.3(2) . . ?
O1 C11 C10 124.9(3) . . ?
O2 C11 C10 110.7(2) . . ?
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 . . ?
O4 C13 O3 124.6(2) . . ?
O4 C13 C10 125.3(3) . . ?
O3 C13 C10 110.1(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C17 123.9(2) . . ?
C18 C16 C15 124.1(3) . . ?
C17 C16 C15 111.9(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 120.1(2) . . ?
C16 C18 C8 126.9(2) . . ?
C19 C18 C8 112.9(2) . . ?
F1 C19 F3 107.3(3) . . ?
F1 C19 F2 103.9(3) . . ?
F3 C19 F2 102.0(3) . . ?
F1 C19 C18 114.9(3) . . ?
F3 C19 C18 114.1(2) . . ?
F2 C19 C18 113.3(3) . . ?

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 -1.2(5) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C2 C3 C4 C5 1.7(6) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 -1.8(4) . . . . ?
C4 C5 C6 C7 174.0(3) . . . . ?
C2 C1 C6 C5 2.6(4) . . . . ?
C2 C1 C6 C7 -173.4(3) . . . . ?
C8 O5 C7 C6 -164.66(18) . . . . ?
C8 O5 C7 C10 -39.4(2) . . . . ?
C5 C6 C7 O5 24.7(3) . . . . ?
C1 C6 C7 O5 -159.5(2) . . . . ?
C5 C6 C7 C10 -94.5(3) . . . . ?
C1 C6 C7 C10 81.4(3) . . . . ?
C7 O5 C8 C18 169.00(18) . . . . ?
C7 O5 C8 C9 44.3(2) . . . . ?
O5 C8 C9 C10 -30.3(2) . . . . ?
C18 C8 C9 C10 -153.91(19) . . . . ?
C8 C9 C10 C11 124.1(2) . . . . ?
C8 C9 C10 C13 -112.9(2) . . . . ?
C8 C9 C10 C7 6.9(2) . . . . ?
O5 C7 C10 C11 -99.3(2) . . . . ?
C6 C7 C10 C11 23.1(3) . . . . ?
O5 C7 C10 C13 138.65(19) . . . . ?
C6 C7 C10 C13 -99.0(2) . . . . ?
O5 C7 C10 C9 18.9(2) . . . . ?
C6 C7 C10 C9 141.2(2) . . . . ?
C12 O2 C11 O1 -4.6(4) . . . . ?
C12 O2 C11 C10 171.7(2) . . . . ?
C13 C10 C11 O1 -150.9(3) . . . . ?
C9 C10 C11 O1 -26.7(3) . . . . ?
C7 C10 C11 O1 85.9(3) . . . . ?
C13 C10 C11 O2 32.8(3) . . . . ?
C9 C10 C11 O2 157.0(2) . . . . ?
C7 C10 C11 O2 -90.4(2) . . . . ?
C14 O3 C13 O4 2.4(4) . . . . ?
C14 O3 C13 C10 -177.8(2) . . . . ?
C11 C10 C13 O4 -119.3(3) . . . . ?
C9 C10 C13 O4 116.9(3) . . . . ?
C7 C10 C13 O4 2.8(4) . . . . ?
C11 C10 C13 O3 60.9(3) . . . . ?
C9 C10 C13 O3 -62.9(3) . . . . ?
C7 C10 C13 O3 -177.0(2) . . . . ?
C17 C16 C18 C19 176.1(3) . . . . ?
C15 C16 C18 C19 -3.7(4) . . . . ?
C17 C16 C18 C8 -0.5(4) . . . . ?
C15 C16 C18 C8 179.7(2) . . . . ?
O5 C8 C18 C16 -33.0(3) . . . . ?
C9 C8 C18 C16 85.9(3) . . . . ?
O5 C8 C18 C19 150.2(2) . . . . ?
C9 C8 C18 C19 -90.9(3) . . . . ?
C16 C18 C19 F1 65.9(4) . . . . ?
C8 C18 C19 F1 -117.0(3) . . . . ?
C16 C18 C19 F3 -169.6(3) . . . . ?
C8 C18 C19 F3 7.5(4) . . . . ?
C16 C18 C19 F2 -53.4(4) . . . . ?
C8 C18 C19 F2 123.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.054
