# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_8
_database_code_depnum_ccdc_archive 'CCDC 1028349'
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;

# RX 1728 Guillot ICMMO

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H27 F N2 O4'
_chemical_formula_sum            'C19 H27 F N2 O4'
_chemical_melting_point          ?

_exptl_crystal_description       bloc
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         366.43

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           tetragonal
_symmetry_space_group_name_H-M   'P 43'
_symmetry_int_tables_number      78
_chemical_absolute_configuration ad

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   10.1585(4)
_cell_length_b                   10.1585(4)
_cell_length_c                   19.0174(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1962.50(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      32.15
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23939
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         32.15
_reflns_number_total             5245
_reflns_number_gt                4955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0540P)²+0.1521P] 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_abs_structure_details 
;
 Flack x determined using 1790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(17)
_refine_ls_number_reflns         5245
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.33676(7) 0.38066(7) 0.01027(4) 0.01996(15) Uani 1 1 d . . .
O1 O 0.96133(10) -0.04344(9) 0.09192(6) 0.0279(2) Uani 1 1 d . . .
C5 C 0.74032(10) 0.29740(10) 0.12439(6) 0.01441(19) Uani 1 1 d . . .
C11 C 0.29691(11) 0.40116(10) 0.07958(6) 0.0145(2) Uani 1 1 d . . .
C10 C 0.41707(10) 0.40218(10) 0.12731(6) 0.01304(19) Uani 1 1 d . . .
C7 C 0.84724(12) 0.10318(11) 0.17326(6) 0.0187(2) Uani 1 1 d . . .
H7 H 0.8680 0.0515 0.2121 0.022 Uiso 1 1 calc R . .
C8 C 0.65827(10) 0.42110(11) 0.13366(6) 0.0154(2) Uani 1 1 d . . .
H8 H 0.6379 0.4308 0.1838 0.019 Uiso 1 1 calc R . .
C4 C 0.78398(11) 0.25924(11) 0.05790(6) 0.0182(2) Uani 1 1 d . . .
H4 H 0.7632 0.3108 0.0191 0.022 Uiso 1 1 calc R . .
C6 C 0.77330(11) 0.21845(11) 0.18130(6) 0.0167(2) Uani 1 1 d . . .
H6 H 0.7455 0.2428 0.2260 0.020 Uiso 1 1 calc R . .
C3 C 0.85788(12) 0.14570(12) 0.04867(7) 0.0209(2) Uani 1 1 d . . .
H3 H 0.8866 0.1218 0.0040 0.025 Uiso 1 1 calc R . .
C14 C 0.20815(11) 0.52442(11) 0.08904(6) 0.0166(2) Uani 1 1 d . . .
H14 H 0.1653 0.5459 0.0443 0.020 Uiso 1 1 calc R . .
C12 C 0.18130(11) 0.31496(12) 0.10375(7) 0.0211(2) Uani 1 1 d . . .
H12A H 0.2051 0.2500 0.1389 0.025 Uiso 1 1 calc R . .
H12B H 0.1327 0.2749 0.0654 0.025 Uiso 1 1 calc R . .
C1 C 0.97975(15) -0.13554(13) 0.14772(8) 0.0293(3) Uani 1 1 d . . .
H1A H 1.0322 -0.0960 0.1840 0.044 Uiso 1 1 calc R . .
H1B H 1.0238 -0.2123 0.1300 0.044 Uiso 1 1 calc R . .
H1C H 0.8957 -0.1602 0.1666 0.044 Uiso 1 1 calc R . .
C9 C 0.72926(12) 0.54533(11) 0.10925(7) 0.0222(2) Uani 1 1 d . . .
H9A H 0.7515 0.5371 0.0604 0.033 Uiso 1 1 calc R . .
H9B H 0.8082 0.5569 0.1363 0.033 Uiso 1 1 calc R . .
H9C H 0.6728 0.6201 0.1157 0.033 Uiso 1 1 calc R . .
C13 C 0.11488(12) 0.43938(12) 0.13442(8) 0.0245(3) Uani 1 1 d . . .
H13A H 0.0227 0.4482 0.1220 0.029 Uiso 1 1 calc R . .
H13B H 0.1277 0.4501 0.1846 0.029 Uiso 1 1 calc R . .
C2 C 0.88898(11) 0.06736(11) 0.10676(7) 0.0181(2) Uani 1 1 d . . .
N1 N 0.53321(9) 0.40958(9) 0.09498(5) 0.01531(18) Uani 1 1 d . . .
H1 H 0.5352 0.4076 0.0498 0.018 Uiso 1 1 calc R . .
O2 O 0.40079(8) 0.40033(8) 0.19163(4) 0.01780(16) Uani 1 1 d . . .
N2 N 0.25985(10) 0.64182(9) 0.12017(5) 0.01676(18) Uani 1 1 d . . .
H2 H 0.2579 0.6501 0.1652 0.020 Uiso 1 1 calc R . .
O4 O 0.35716(9) 0.83534(8) 0.12445(5) 0.02172(18) Uani 1 1 d . . .
O3 O 0.31401(12) 0.74322(9) 0.01704(5) 0.0303(2) Uani 1 1 d . . .
C15 C 0.31215(12) 0.74089(11) 0.08063(6) 0.0187(2) Uani 1 1 d . . .
C18 C 0.34247(14) 1.02595(12) 0.04471(8) 0.0252(3) Uani 1 1 d . . .
H18A H 0.3407 0.9799 0.0007 0.038 Uiso 1 1 calc R . .
H18B H 0.3783 1.1124 0.0378 0.038 Uiso 1 1 calc R . .
H18C H 0.2546 1.0331 0.0629 0.038 Uiso 1 1 calc R . .
C16 C 0.42769(12) 0.95066(11) 0.09674(7) 0.0200(2) Uani 1 1 d . . .
C19 C 0.45025(16) 1.03169(13) 0.16309(8) 0.0307(3) Uani 1 1 d . . .
H19A H 0.3670 1.0534 0.1839 0.046 Uiso 1 1 calc R . .
H19B H 0.4964 1.1111 0.1513 0.046 Uiso 1 1 calc R . .
H19C H 0.5016 0.9815 0.1959 0.046 Uiso 1 1 calc R . .
C17 C 0.55714(14) 0.90772(14) 0.06410(9) 0.0317(3) Uani 1 1 d . . .
H17A H 0.6072 0.8587 0.0980 0.048 Uiso 1 1 calc R . .
H17B H 0.6062 0.9840 0.0498 0.048 Uiso 1 1 calc R . .
H17C H 0.5399 0.8534 0.0238 0.048 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 C11 1.3945(13) . ?
O1 C2 1.3736(13) . ?
O1 C1 1.4270(17) . ?
C5 C6 1.3881(16) . ?
C5 C4 1.3950(16) . ?
C5 C8 1.5182(15) . ?
C11 C10 1.5212(15) . ?
C11 C12 1.5353(15) . ?
C11 C14 1.5534(15) . ?
C10 O2 1.2344(14) . ?
C10 N1 1.3326(14) . ?
C7 C2 1.3826(17) . ?
C7 C6 1.3996(16) . ?
C8 N1 1.4727(14) . ?
C8 C9 1.5259(17) . ?
C4 C3 1.3873(16) . ?
C3 C2 1.3977(17) . ?
C14 N2 1.4312(14) . ?
C14 C13 1.5456(17) . ?
C12 C13 1.5469(16) . ?
N2 C15 1.3640(16) . ?
O4 C15 1.3506(14) . ?
O4 C16 1.4709(14) . ?
O3 C15 1.2098(15) . ?
C18 C16 1.5209(18) . ?
C16 C17 1.5182(19) . ?
C16 C19 1.5240(19) . ?

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
C2 O1 C1 117.04(11) . . ?
C6 C5 C4 118.00(10) . . ?
C6 C5 C8 121.35(10) . . ?
C4 C5 C8 120.65(10) . . ?
F1 C11 C10 109.40(9) . . ?
F1 C11 C12 114.82(9) . . ?
C10 C11 C12 116.04(10) . . ?
F1 C11 C14 113.48(9) . . ?
C10 C11 C14 113.02(9) . . ?
C12 C11 C14 88.92(8) . . ?
O2 C10 N1 125.22(10) . . ?
O2 C10 C11 118.93(9) . . ?
N1 C10 C11 115.81(10) . . ?
C2 C7 C6 118.99(10) . . ?
N1 C8 C5 110.48(9) . . ?
N1 C8 C9 108.76(10) . . ?
C5 C8 C9 112.94(9) . . ?
C3 C4 C5 121.18(11) . . ?
C5 C6 C7 121.86(11) . . ?
C4 C3 C2 119.72(11) . . ?
N2 C14 C13 117.37(10) . . ?
N2 C14 C11 120.44(9) . . ?
C13 C14 C11 88.28(9) . . ?
C11 C12 C13 88.88(8) . . ?
C14 C13 C12 88.78(9) . . ?
O1 C2 C7 124.59(11) . . ?
O1 C2 C3 115.16(11) . . ?
C7 C2 C3 120.25(10) . . ?
C10 N1 C8 122.53(10) . . ?
C15 N2 C14 121.99(10) . . ?
C15 O4 C16 120.64(10) . . ?
O3 C15 O4 126.70(11) . . ?
O3 C15 N2 124.87(11) . . ?
O4 C15 N2 108.42(10) . . ?
O4 C16 C17 109.85(10) . . ?
O4 C16 C18 110.87(10) . . ?
C17 C16 C18 111.81(11) . . ?
O4 C16 C19 101.93(10) . . ?
C17 C16 C19 111.32(12) . . ?
C18 C16 C19 110.65(11) . . ?

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_12
_database_code_depnum_ccdc_archive 'CCDC 1028350'
_audit_update_record             
;
2014-10-09 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;
# RX 2006 Guillot ICMMO
#boddaertcp3a 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C32 H40 F4 N4 O7'
_chemical_formula_sum            'C32 H40 F4 N4 O7'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         668.68

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration syn

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'

_cell_length_a                   5.3500(9)
_cell_length_b                   20.200(3)
_cell_length_c                   29.927(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3234.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50560
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_sigmaI/netI    0.0970
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         30.49
_reflns_number_total             9833
_reflns_number_gt                6330
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0833P)²+0.3628P] 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     SHELXL
_refine_ls_extinction_coef       0.0059(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_number_reflns         9833
_refine_ls_number_parameters     428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003

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
F2 F 0.0842(3) 0.73911(8) 0.56634(5) 0.0219(4) Uani 1 1 d . . .
F3 F 0.5189(3) 0.50352(8) 0.63963(5) 0.0221(4) Uani 1 1 d . . .
F1 F 0.4706(3) 0.76331(8) 0.74145(5) 0.0227(4) Uani 1 1 d . . .
O4 O 0.6102(4) 0.67246(10) 0.61921(6) 0.0212(4) Uani 1 1 d . . .
F4 F 0.2049(5) 0.47158(13) 0.45324(6) 0.0531(6) Uani 1 1 d . . .
O1 O 0.2576(4) 1.00514(10) 0.70578(7) 0.0229(4) Uani 1 1 d . . .
O2 O 0.5615(4) 0.94140(10) 0.73845(6) 0.0240(4) Uani 1 1 d . . .
O3 O -0.0446(4) 0.80540(10) 0.67483(6) 0.0231(4) Uani 1 1 d . . .
N4 N 0.4096(5) 0.52998(12) 0.55691(7) 0.0220(5) Uani 1 1 d . . .
H4 H 0.5552 0.5215 0.5677 0.026 Uiso 1 1 calc R . .
O5 O -0.0047(4) 0.53532(10) 0.57244(6) 0.0249(5) Uani 1 1 d . . .
N3 N 0.1949(4) 0.65335(12) 0.62904(7) 0.0207(5) Uani 1 1 d . . .
H3 H 0.0454 0.6666 0.6233 0.025 Uiso 1 1 calc R . .
N2 N 0.3725(4) 0.80535(11) 0.66082(7) 0.0183(5) Uani 1 1 d . . .
H2 H 0.5197 0.8048 0.6724 0.022 Uiso 1 1 calc R . .
O7 O 0.7641(5) 0.43905(12) 0.51008(9) 0.0414(6) Uani 1 1 d . . .
C19 C 0.2757(5) 0.52795(14) 0.63391(9) 0.0176(5) Uani 1 1 d . . .
N1 N 0.1481(4) 0.91537(11) 0.74290(8) 0.0194(5) Uani 1 1 d . . .
H1 H -0.0016 0.9287 0.7375 0.023 Uiso 1 1 calc R . .
C14 C 0.3217(5) 0.74750(14) 0.58501(9) 0.0178(6) Uani 1 1 d . . .
C15 C 0.3908(5) 0.68708(14) 0.61175(8) 0.0173(5) Uani 1 1 d . . .
C9 C 0.2293(5) 0.78979(14) 0.73687(9) 0.0180(5) Uani 1 1 d . . .
C16 C 0.2310(5) 0.59577(14) 0.65678(9) 0.0187(6) Uani 1 1 d . . .
H16 H 0.3595 0.6042 0.6794 0.022 Uiso 1 1 calc R . .
C10 C 0.1731(5) 0.79980(13) 0.68791(9) 0.0182(6) Uani 1 1 d . . .
C21 C 0.3880(6) 0.54394(15) 0.50964(9) 0.0249(6) Uani 1 1 d . . .
H21 H 0.2277 0.5660 0.5042 0.030 Uiso 1 1 calc R . .
C6 C 0.1844(5) 0.85324(14) 0.76585(9) 0.0187(6) Uani 1 1 d . . .
H6 H 0.3142 0.8575 0.7888 0.022 Uiso 1 1 calc R . .
C1 C 0.4342(6) 1.04827(14) 0.68216(10) 0.0250(6) Uani 1 1 d . . .
C20 C 0.2131(5) 0.52964(13) 0.58474(9) 0.0183(5) Uani 1 1 d . . .
C5 C 0.3417(5) 0.95302(14) 0.72976(9) 0.0201(6) Uani 1 1 d . . .
C11 C 0.3476(5) 0.81215(13) 0.61311(9) 0.0175(5) Uani 1 1 d . . .
H11 H 0.2137 0.8434 0.6057 0.021 Uiso 1 1 calc R . .
C17 C -0.0047(5) 0.56655(15) 0.67848(9) 0.0226(6) Uani 1 1 d . . .
H17A H -0.1588 0.5797 0.6639 0.027 Uiso 1 1 calc R . .
H17B H -0.0143 0.5739 0.7105 0.027 Uiso 1 1 calc R . .
C12 C 0.5869(6) 0.82856(15) 0.58667(9) 0.0219(6) Uani 1 1 d . . .
H12A H 0.7399 0.8196 0.6030 0.026 Uiso 1 1 calc R . .
H12B H 0.5884 0.8729 0.5742 0.026 Uiso 1 1 calc R . .
C18 C 0.0842(5) 0.49642(15) 0.66567(9) 0.0228(6) Uani 1 1 d . . .
H18A H 0.1588 0.4721 0.6902 0.027 Uiso 1 1 calc R . .
H18B H -0.0420 0.4701 0.6506 0.027 Uiso 1 1 calc R . .
C8 C 0.0324(6) 0.75380(14) 0.76512(10) 0.0239(6) Uani 1 1 d . . .
H8A H 0.1029 0.7234 0.7868 0.029 Uiso 1 1 calc R . .
H8B H -0.0967 0.7324 0.7476 0.029 Uiso 1 1 calc R . .
C24 C 0.4256(7) 0.48982(17) 0.47384(10) 0.0330(8) Uani 1 1 d . . .
C13 C 0.5179(5) 0.77398(14) 0.55220(9) 0.0209(6) Uani 1 1 d . . .
H13A H 0.4477 0.7911 0.5246 0.025 Uiso 1 1 calc R . .
H13B H 0.6526 0.7431 0.5462 0.025 Uiso 1 1 calc R . .
C3 C 0.2595(7) 1.09199(18) 0.65476(12) 0.0385(8) Uani 1 1 d . . .
H3A H 0.1591 1.1183 0.6745 0.058 Uiso 1 1 calc R . .
H3B H 0.1531 1.0647 0.6367 0.058 Uiso 1 1 calc R . .
H3C H 0.3565 1.1205 0.6358 0.058 Uiso 1 1 calc R . .
O6 O 0.5020(8) 0.37370(14) 0.47228(11) 0.0740(10) Uani 1 1 d . . .
C22 C 0.5974(6) 0.58505(17) 0.48795(10) 0.0305(7) Uani 1 1 d . . .
H22A H 0.5511 0.6307 0.4820 0.037 Uiso 1 1 calc R . .
H22B H 0.7557 0.5826 0.5037 0.037 Uiso 1 1 calc R . .
C2 C 0.5826(7) 1.08875(18) 0.71533(12) 0.0401(9) Uani 1 1 d . . .
H2A H 0.6862 1.0599 0.7328 0.060 Uiso 1 1 calc R . .
H2B H 0.4700 1.1122 0.7346 0.060 Uiso 1 1 calc R . .
H2C H 0.6857 1.1198 0.6996 0.060 Uiso 1 1 calc R . .
C7 C -0.0488(6) 0.82073(14) 0.78523(10) 0.0231(6) Uani 1 1 d . . .
H7A H -0.2036 0.8377 0.7728 0.028 Uiso 1 1 calc R . .
H7B H -0.0538 0.8209 0.8176 0.028 Uiso 1 1 calc R . .
C25 C 0.5647(8) 0.42703(17) 0.48578(12) 0.0401(9) Uani 1 1 d . . .
C23 C 0.5828(7) 0.53974(16) 0.44651(10) 0.0328(7) Uani 1 1 d . . .
H23A H 0.7435 0.5225 0.4370 0.039 Uiso 1 1 calc R . .
H23B H 0.4932 0.5592 0.4216 0.039 Uiso 1 1 calc R . .
C4 C 0.6025(6) 1.00828(18) 0.65141(10) 0.0327(7) Uani 1 1 d . . .
H4A H 0.5035 0.9771 0.6349 0.049 Uiso 1 1 calc R . .
H4B H 0.7243 0.9849 0.6689 0.049 Uiso 1 1 calc R . .
H4C H 0.6862 1.0376 0.6310 0.049 Uiso 1 1 calc R . .
C27 C 0.7926(9) 0.33954(19) 0.55762(14) 0.0545(11) Uani 1 1 d . . .
C29 C 0.5341(8) 0.3354(2) 0.62170(11) 0.0465(10) Uani 1 1 d . . .
H29 H 0.4348 0.3573 0.6425 0.056 Uiso 1 1 calc R . .
C28 C 0.6485(9) 0.3672(2) 0.59117(14) 0.0512(11) Uani 1 1 d . . .
H28 H 0.6340 0.4130 0.5914 0.061 Uiso 1 1 calc R . .
C30 C 0.5636(12) 0.2638(2) 0.62296(16) 0.0755(16) Uani 1 1 d . . .
H30 H 0.4764 0.2390 0.6440 0.091 Uiso 1 1 calc R . .
C26 C 0.9212(9) 0.3820(2) 0.52322(15) 0.0569(12) Uani 1 1 d . . .
H26A H 1.0783 0.3980 0.5353 0.068 Uiso 1 1 calc R . .
H26B H 0.9582 0.3555 0.4970 0.068 Uiso 1 1 calc R . .
C31 C 0.7201(15) 0.2325(2) 0.5931(2) 0.114(3) Uani 1 1 d . . .
H31 H 0.7588 0.1878 0.5956 0.136 Uiso 1 1 calc R . .
C32 C 0.8185(14) 0.2722(2) 0.55840(19) 0.093(2) Uani 1 1 d . . .
H32 H 0.9043 0.2518 0.5352 0.112 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
F2 C14 1.398(3) . ?
F3 C19 1.402(3) . ?
F1 C9 1.404(3) . ?
O4 C15 1.231(3) . ?
F4 C24 1.382(4) . ?
O1 C5 1.351(3) . ?
O1 C1 1.467(4) . ?
O2 C5 1.227(4) . ?
O3 C10 1.234(3) . ?
N4 C20 1.341(4) . ?
N4 C21 1.447(4) . ?
O5 C20 1.228(4) . ?
N3 C15 1.353(4) . ?
N3 C16 1.442(4) . ?
N2 C10 1.345(4) . ?
N2 C11 1.440(3) . ?
O7 C25 1.314(5) . ?
O7 C26 1.480(5) . ?
C19 C20 1.510(4) . ?
C19 C18 1.536(4) . ?
C19 C16 1.550(4) . ?
N1 C5 1.344(4) . ?
N1 C6 1.444(4) . ?
C14 C15 1.506(4) . ?
C14 C13 1.534(4) . ?
C14 C11 1.559(4) . ?
C9 C10 1.509(4) . ?
C9 C8 1.534(4) . ?
C9 C6 1.566(4) . ?
C16 C17 1.536(4) . ?
C21 C22 1.538(4) . ?
C21 C24 1.544(4) . ?
C6 C7 1.525(4) . ?
C1 C2 1.511(4) . ?
C1 C4 1.520(5) . ?
C1 C3 1.525(5) . ?
C11 C12 1.541(4) . ?
C17 C18 1.543(4) . ?
C12 C13 1.554(4) . ?
C8 C7 1.542(4) . ?
C24 C25 1.513(5) . ?
C24 C23 1.547(5) . ?
O6 C25 1.198(4) . ?
C22 C23 1.543(5) . ?
C27 C32 1.367(6) . ?
C27 C28 1.383(6) . ?
C27 C26 1.506(6) . ?
C29 C28 1.273(5) . ?
C29 C30 1.457(6) . ?
C30 C31 1.379(7) . ?
C31 C32 1.414(7) . ?

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
C5 O1 C1 120.3(2) . . ?
C20 N4 C21 123.0(2) . . ?
C15 N3 C16 121.5(2) . . ?
C10 N2 C11 122.2(2) . . ?
C25 O7 C26 117.7(3) . . ?
F3 C19 C20 109.4(2) . . ?
F3 C19 C18 113.4(2) . . ?
C20 C19 C18 117.7(2) . . ?
F3 C19 C16 113.6(2) . . ?
C20 C19 C16 112.1(2) . . ?
C18 C19 C16 89.4(2) . . ?
C5 N1 C6 121.8(2) . . ?
F2 C14 C15 109.7(2) . . ?
F2 C14 C13 114.1(2) . . ?
C15 C14 C13 117.1(2) . . ?
F2 C14 C11 113.4(2) . . ?
C15 C14 C11 111.7(2) . . ?
C13 C14 C11 89.6(2) . . ?
O4 C15 N3 123.3(3) . . ?
O4 C15 C14 121.7(3) . . ?
N3 C15 C14 114.9(2) . . ?
F1 C9 C10 109.2(2) . . ?
F1 C9 C8 113.4(2) . . ?
C10 C9 C8 117.5(2) . . ?
F1 C9 C6 113.5(2) . . ?
C10 C9 C6 113.4(2) . . ?
C8 C9 C6 88.7(2) . . ?
N3 C16 C17 116.3(2) . . ?
N3 C16 C19 118.6(2) . . ?
C17 C16 C19 88.5(2) . . ?
O3 C10 N2 123.4(2) . . ?
O3 C10 C9 120.6(3) . . ?
N2 C10 C9 116.0(2) . . ?
N4 C21 C22 117.3(3) . . ?
N4 C21 C24 122.0(3) . . ?
C22 C21 C24 89.7(2) . . ?
N1 C6 C7 116.4(2) . . ?
N1 C6 C9 117.9(2) . . ?
C7 C6 C9 89.1(2) . . ?
O1 C1 C2 110.1(2) . . ?
O1 C1 C4 111.0(2) . . ?
C2 C1 C4 112.0(3) . . ?
O1 C1 C3 102.0(3) . . ?
C2 C1 C3 111.2(3) . . ?
C4 C1 C3 110.2(3) . . ?
O5 C20 N4 123.9(3) . . ?
O5 C20 C19 120.3(2) . . ?
N4 C20 C19 115.6(2) . . ?
O2 C5 N1 124.6(3) . . ?
O2 C5 O1 125.5(3) . . ?
N1 C5 O1 109.9(2) . . ?
N2 C11 C12 116.9(2) . . ?
N2 C11 C14 117.6(2) . . ?
C12 C11 C14 88.7(2) . . ?
C16 C17 C18 89.7(2) . . ?
C11 C12 C13 89.5(2) . . ?
C19 C18 C17 88.8(2) . . ?
C9 C8 C7 89.6(2) . . ?
F4 C24 C25 107.6(3) . . ?
F4 C24 C23 113.7(3) . . ?
C25 C24 C23 113.8(3) . . ?
F4 C24 C21 112.7(3) . . ?
C25 C24 C21 119.6(3) . . ?
C23 C24 C21 88.6(2) . . ?
C14 C13 C12 89.1(2) . . ?
C23 C22 C21 89.0(2) . . ?
C6 C7 C8 89.9(2) . . ?
O6 C25 O7 125.5(4) . . ?
O6 C25 C24 122.4(4) . . ?
O7 C25 C24 112.0(3) . . ?
C22 C23 C24 89.4(2) . . ?
C32 C27 C28 116.4(4) . . ?
C32 C27 C26 122.1(4) . . ?
C28 C27 C26 121.4(4) . . ?
C28 C29 C30 117.8(4) . . ?
C29 C28 C27 125.9(4) . . ?
C31 C30 C29 120.3(4) . . ?
O7 C26 C27 111.4(4) . . ?
C30 C31 C32 116.2(4) . . ?
C27 C32 C31 122.7(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.077

