# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1870545'
_audit_update_record             
;
2018-09-29 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C34H27F6N2O5S
_chemical_formula_sum            'C34 H27 F6 N2 O5 S'
_chemical_formula_weight         689.64

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'
S S 0.1246 0.1234 '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                   9.0274(4)
_cell_length_b                   12.8372(5)
_cell_length_c                   15.1428(6)
_cell_angle_alpha                80.836(3)
_cell_angle_beta                 75.449(4)
_cell_angle_gamma                70.099(4)
_cell_volume                     1591.87(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5019
_cell_measurement_theta_min      3.7720
_cell_measurement_theta_max      23.8530

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             710
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.09316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            18299
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         24.50
_reflns_number_total             5274
_reflns_number_gt                3372
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0847P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5301
_refine_ls_number_parameters     458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1684
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C23 C 0.9786(4) 0.8140(2) 0.59604(19) 0.0555(7) Uani 1 1 d . A .
C24 C 0.9193(3) 0.9033(2) 0.64916(19) 0.0533(7) Uani 1 1 d . . .
C26 C 1.0994(5) 0.7825(3) 0.7574(2) 0.0767(11) Uani 1 1 d . . .
H26 H 1.137(5) 0.788(3) 0.795(3) 0.092 Uiso 1 1 d . . .
C25 C 0.9850(4) 0.8916(3) 0.7326(2) 0.0692(9) Uani 1 1 d . A .
C28 C 1.1001(5) 0.7065(2) 0.6172(2) 0.0776(10) Uani 1 1 d . . .
C32 C 1.5110(6) 0.3949(4) 0.7597(4) 0.1006(13) Uani 1 1 d . A .
H32 H 1.5873 0.3285 0.7741 0.121 Uiso 1 1 calc R . .
C33 C 1.5447(5) 0.4568(3) 0.6801(4) 0.0979(13) Uani 1 1 d . . .
H33 H 1.6440 0.4320 0.6402 0.117 Uiso 1 1 calc R . .
C34 C 1.4319(4) 0.5570(3) 0.6576(3) 0.0877(11) Uani 1 1 d . A .
H34 H 1.4558 0.5988 0.6030 0.105 Uiso 1 1 calc R . .
C29 C 1.2854(5) 0.5933(3) 0.7166(3) 0.0953(13) Uani 1 1 d . . .
C27 C 1.1896(11) 0.7181(7) 0.6823(6) 0.059(2) Uani 0.584(17) 1 d P A 1
H27 H 1.2704 0.7528 0.6477 0.070 Uiso 0.584(17) 1 calc PR A 1
N2 N 0.5841(3) 0.07901(17) 0.31560(15) 0.0534(6) Uani 1 1 d . . .
H2 H 0.6357 0.0263 0.3499 0.064 Uiso 1 1 calc R . .
F3 F 0.4323(3) 0.37623(14) 0.07816(15) 0.0866(6) Uani 1 1 d . . .
F2 F 0.2247(2) 0.32099(17) 0.11598(15) 0.0955(7) Uani 1 1 d . . .
O2 O 0.4832(3) 0.17788(17) 0.01777(15) 0.0723(6) Uani 1 1 d . . .
C6 C 0.5304(3) 0.1422(2) 0.16731(19) 0.0470(7) Uani 1 1 d . . .
F1 F 0.2540(3) 0.42948(15) 0.19737(14) 0.1042(8) Uani 1 1 d . . .
C5 C 0.6099(3) 0.0627(2) 0.22644(18) 0.0475(7) Uani 1 1 d . . .
O1 O 0.4688(3) 0.18339(18) 0.43651(15) 0.0826(7) Uani 1 1 d . . .
C10 C 0.7319(3) -0.0458(2) 0.19906(18) 0.0518(7) Uani 1 1 d . . .
H10A H 0.6810 -0.1037 0.2148 0.062 Uiso 1 1 calc R . .
H10B H 0.8170 -0.0647 0.2327 0.062 Uiso 1 1 calc R . .
C7 C 0.5575(3) 0.1154(2) 0.0720(2) 0.0520(7) Uani 1 1 d . . .
C2 C 0.4229(3) 0.2441(2) 0.2052(2) 0.0530(7) Uani 1 1 d . . .
C3 C 0.3983(3) 0.2571(2) 0.2950(2) 0.0601(8) Uani 1 1 d . . .
H3 H 0.3249 0.3226 0.3179 0.072 Uiso 1 1 calc R . .
C9 C 0.8046(3) -0.0409(2) 0.09654(19) 0.0597(8) Uani 1 1 d . . .
H9 H 0.8645 0.0126 0.0846 0.072 Uiso 1 1 calc R . .
C8 C 0.6719(4) 0.0054(2) 0.0456(2) 0.0630(8) Uani 1 1 d . . .
H8A H 0.7191 0.0118 -0.0193 0.076 Uiso 1 1 calc R . .
H8B H 0.6120 -0.0469 0.0551 0.076 Uiso 1 1 calc R . .
C11 C 0.9257(4) -0.1519(2) 0.07065(18) 0.0560(7) Uani 1 1 d . . .
C14 C 1.1564(4) -0.3539(3) 0.0272(2) 0.0771(10) Uani 1 1 d . . .
H14 H 1.2339 -0.4216 0.0124 0.093 Uiso 1 1 calc R . .
C16 C 1.0807(4) -0.1754(3) 0.0803(2) 0.0663(8) Uani 1 1 d . . .
H16 H 1.1085 -0.1225 0.1023 0.080 Uiso 1 1 calc R . .
C4 C 0.4805(3) 0.1745(2) 0.3559(2) 0.0582(8) Uani 1 1 d . . .
C1 C 0.3349(4) 0.3416(3) 0.1481(3) 0.0702(9) Uani 1 1 d . . .
C12 C 0.8887(4) -0.2316(3) 0.0386(2) 0.0729(9) Uani 1 1 d . . .
H12 H 0.7847 -0.2172 0.0304 0.088 Uiso 1 1 calc R . .
C15 C 1.1966(4) -0.2751(3) 0.0585(2) 0.0740(9) Uani 1 1 d . . .
H15 H 1.3015 -0.2887 0.0649 0.089 Uiso 1 1 calc R . .
C13 C 1.0029(5) -0.3330(3) 0.0180(2) 0.0810(10) Uani 1 1 d . . .
H13 H 0.9747 -0.3870 -0.0022 0.097 Uiso 1 1 calc R . .
N1 N 0.9271(3) 0.82108(18) 0.51816(16) 0.0577(6) Uani 1 1 d . . .
H1 H 0.9656 0.7635 0.4872 0.069 Uiso 1 1 calc R A .
C20 C 0.8019(3) 0.9999(2) 0.6192(2) 0.0575(7) Uani 1 1 d . A .
C21 C 0.7548(4) 1.0034(2) 0.5410(2) 0.0619(8) Uani 1 1 d . . .
H21 H 0.6780 1.0673 0.5231 0.074 Uiso 1 1 calc R A .
C22 C 0.8184(4) 0.9127(2) 0.4845(2) 0.0570(7) Uani 1 1 d . A .
O4 O 0.9478(4) 0.9674(2) 0.77977(19) 0.1197(11) Uani 1 1 d . . .
O3 O 0.7854(3) 0.91108(16) 0.41065(14) 0.0719(6) Uani 1 1 d . . .
C19 C 0.7213(5) 1.1004(3) 0.6727(3) 0.0788(10) Uani 1 1 d . . .
S1 S -0.02824(10) 0.57745(5) 0.38195(5) 0.0587(3) Uani 1 1 d . . .
O5 O 0.0425(3) 0.61830(15) 0.44369(14) 0.0672(6) Uani 1 1 d . . .
C17 C -0.2363(4) 0.6162(3) 0.4264(3) 0.0953(12) Uani 1 1 d . . .
H17A H -0.2577 0.5734 0.4834 0.143 Uiso 1 1 calc R . .
H17B H -0.2892 0.6026 0.3838 0.143 Uiso 1 1 calc R . .
H17C H -0.2760 0.6938 0.4364 0.143 Uiso 1 1 calc R . .
C18 C -0.0244(6) 0.6691(3) 0.2822(2) 0.0968(13) Uani 1 1 d . . .
H18A H -0.0731 0.7443 0.2986 0.145 Uiso 1 1 calc R . .
H18B H -0.0833 0.6544 0.2434 0.145 Uiso 1 1 calc R . .
H18C H 0.0852 0.6583 0.2501 0.145 Uiso 1 1 calc R . .
C27A C 1.1237(15) 0.6779(9) 0.7064(7) 0.052(3) Uani 0.416(17) 1 d P A 2
H27A H 1.0406 0.6447 0.7398 0.063 Uiso 0.416(17) 1 calc PR A 2
F4 F 0.8214(3) 1.15214(15) 0.67874(15) 0.0996(7) Uani 1 1 d . A .
F5A F 0.5909(19) 1.163(3) 0.649(2) 0.121(6) Uani 0.55(7) 1 d P A 1
F6 F 0.6480(3) 1.0784(2) 0.75677(17) 0.1151(8) Uani 1 1 d . A .
C31 C 1.3672(7) 0.4299(4) 0.8176(3) 0.1233(17) Uani 1 1 d . . .
H31 H 1.3444 0.3877 0.8720 0.148 Uiso 1 1 calc R A .
C30 C 1.2537(6) 0.5278(4) 0.7965(3) 0.1297(19) Uani 1 1 d . A .
H30 H 1.1541 0.5504 0.8365 0.156 Uiso 1 1 calc R . .
F5 F 0.635(7) 1.1859(18) 0.619(3) 0.134(10) Uani 0.45(7) 1 d P A 2


_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
C23 N1 1.352(3) . ?
C23 C24 1.381(4) . ?
C23 C28 1.489(4) . ?
C24 C20 1.426(4) . ?
C24 C25 1.491(4) . ?
C26 C27 1.418(7) . ?
C26 C25 1.488(5) . ?
C26 C27A 1.577(11) . ?
C25 O4 1.203(3) . ?
C28 C27A 1.393(9) . ?
C28 C27 1.476(8) . ?
C32 C31 1.346(6) . ?
C32 C33 1.361(6) . ?
C33 C34 1.397(5) . ?
C34 C29 1.372(5) . ?
C29 C30 1.385(6) . ?
C29 C27A 1.522(9) . ?
C29 C27 1.613(8) . ?
N2 C5 1.349(3) . ?
N2 C4 1.386(3) . ?
F3 C1 1.320(4) . ?
F2 C1 1.326(4) . ?
O2 C7 1.212(3) . ?
C6 C5 1.376(4) . ?
C6 C2 1.441(4) . ?
C6 C7 1.478(4) . ?
F1 C1 1.340(3) . ?
C5 C10 1.495(3) . ?
O1 C4 1.218(3) . ?
C10 C9 1.526(4) . ?
C7 C8 1.483(4) . ?
C2 C3 1.349(4) . ?
C2 C1 1.507(4) . ?
C3 C4 1.422(4) . ?
C9 C8 1.489(4) . ?
C9 C11 1.510(4) . ?
C11 C12 1.366(4) . ?
C11 C16 1.368(4) . ?
C14 C13 1.358(5) . ?
C14 C15 1.367(5) . ?
C16 C15 1.375(4) . ?
C12 C13 1.382(4) . ?
N1 C22 1.371(4) . ?
C20 C21 1.345(4) . ?
C20 C19 1.499(4) . ?
C21 C22 1.425(4) . ?
C22 O3 1.233(3) . ?
C19 F5A 1.28(2) . ?
C19 F6 1.314(4) . ?
C19 F4 1.317(4) . ?
C19 F5 1.39(2) . ?
S1 O5 1.497(2) . ?
S1 C17 1.750(4) . ?
S1 C18 1.762(3) . ?
C31 C30 1.375(6) . ?

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
N1 C23 C24 120.0(3) . . ?
N1 C23 C28 115.2(2) . . ?
C24 C23 C28 124.8(3) . . ?
C23 C24 C20 117.4(3) . . ?
C23 C24 C25 117.4(3) . . ?
C20 C24 C25 125.2(3) . . ?
C27 C26 C25 114.6(4) . . ?
C27 C26 C27A 34.1(3) . . ?
C25 C26 C27A 119.4(4) . . ?
O4 C25 C26 119.7(3) . . ?
O4 C25 C24 122.0(3) . . ?
C26 C25 C24 118.4(3) . . ?
C27A C28 C27 36.0(4) . . ?
C27A C28 C23 119.1(4) . . ?
C27 C28 C23 111.3(3) . . ?
C31 C32 C33 119.9(4) . . ?
C32 C33 C34 120.8(4) . . ?
C29 C34 C33 119.4(4) . . ?
C34 C29 C30 118.5(4) . . ?
C34 C29 C27A 133.8(6) . . ?
C30 C29 C27A 105.7(7) . . ?
C34 C29 C27 109.4(6) . . ?
C30 C29 C27 131.6(5) . . ?
C27A C29 C27 32.8(3) . . ?
C26 C27 C28 117.2(6) . . ?
C26 C27 C29 111.4(6) . . ?
C28 C27 C29 106.0(6) . . ?
C5 N2 C4 124.8(2) . . ?
C5 C6 C2 116.4(2) . . ?
C5 C6 C7 118.0(2) . . ?
C2 C6 C7 125.6(2) . . ?
N2 C5 C6 121.2(2) . . ?
N2 C5 C10 114.5(2) . . ?
C6 C5 C10 124.3(2) . . ?
C5 C10 C9 111.4(2) . . ?
O2 C7 C6 121.8(2) . . ?
O2 C7 C8 120.2(3) . . ?
C6 C7 C8 117.9(2) . . ?
C3 C2 C6 120.8(3) . . ?
C3 C2 C1 116.5(2) . . ?
C6 C2 C1 122.7(3) . . ?
C2 C3 C4 122.5(3) . . ?
C8 C9 C11 116.6(2) . . ?
C8 C9 C10 109.0(2) . . ?
C11 C9 C10 110.3(2) . . ?
C7 C8 C9 114.8(2) . . ?
C12 C11 C16 117.6(3) . . ?
C12 C11 C9 123.5(3) . . ?
C16 C11 C9 118.9(3) . . ?
C13 C14 C15 119.8(3) . . ?
C11 C16 C15 121.9(3) . . ?
O1 C4 N2 120.2(3) . . ?
O1 C4 C3 125.5(3) . . ?
N2 C4 C3 114.2(3) . . ?
F3 C1 F2 108.0(3) . . ?
F3 C1 F1 105.8(3) . . ?
F2 C1 F1 105.2(3) . . ?
F3 C1 C2 113.0(3) . . ?
F2 C1 C2 113.0(3) . . ?
F1 C1 C2 111.3(3) . . ?
C11 C12 C13 121.3(3) . . ?
C14 C15 C16 119.5(3) . . ?
C14 C13 C12 120.0(3) . . ?
C23 N1 C22 125.2(2) . . ?
C21 C20 C24 120.5(2) . . ?
C21 C20 C19 116.4(3) . . ?
C24 C20 C19 123.0(3) . . ?
C20 C21 C22 122.4(3) . . ?
O3 C22 N1 119.5(2) . . ?
O3 C22 C21 126.1(3) . . ?
N1 C22 C21 114.4(3) . . ?
F5A C19 F6 94.0(15) . . ?
F5A C19 F4 115.3(15) . . ?
F6 C19 F4 106.9(3) . . ?
F5A C19 F5 26.8(16) . . ?
F6 C19 F5 118(2) . . ?
F4 C19 F5 95(2) . . ?
F5A C19 C20 112.5(9) . . ?
F6 C19 C20 113.5(3) . . ?
F4 C19 C20 113.2(3) . . ?
F5 C19 C20 108.7(12) . . ?
O5 S1 C17 106.38(15) . . ?
O5 S1 C18 105.34(15) . . ?
C17 S1 C18 99.7(2) . . ?
C28 C27A C29 115.7(7) . . ?
C28 C27A C26 112.4(8) . . ?
C29 C27A C26 107.9(8) . . ?
C32 C31 C30 120.3(5) . . ?
C31 C30 C29 121.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_123
_database_code_depnum_ccdc_archive 'CCDC 1872006'
_audit_update_record             
;
2018-10-08 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C10H7F3O3
_chemical_formula_sum            'C10 H7 F3 O3'
_chemical_formula_weight         232.16

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

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

_cell_length_a                   9.877(6)
_cell_length_b                   11.908(7)
_cell_length_c                   16.045(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1887(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7423
_cell_measurement_theta_min      3.057
_cell_measurement_theta_max      18.855

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean None
_diffrn_standards_number         None
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_decay_%        'not measured'
_diffrn_reflns_number            7344
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_sigmaI/netI    0.1338
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.22
_reflns_number_total             3410
_reflns_number_gt                2027
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         3368
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1328
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
F4 F -0.0338(4) -0.9581(3) -0.8139(2) 0.0434(9) Uani 1 1 d . . .
O5 O -0.3400(4) -0.7255(3) -0.9797(2) 0.0313(10) Uani 1 1 d . . .
F6 F 0.0351(3) -0.9919(3) -0.9372(2) 0.0385(9) Uani 1 1 d . . .
F5 F -0.1316(4) -1.0854(3) -0.8848(2) 0.0388(9) Uani 1 1 d . . .
O6 O -0.1394(4) -1.0716(3) -1.0530(3) 0.0415(11) Uani 1 1 d . . .
C16 C -0.1881(6) -0.9823(5) -1.0722(4) 0.0280(13) Uani 1 1 d . . .
C15 C -0.2140(5) -0.8909(4) -1.0115(3) 0.0211(13) Uani 1 1 d . . .
C12 C -0.1739(5) -0.8970(4) -0.9234(3) 0.0228(13) Uani 1 1 d . . .
C14 C -0.2911(5) -0.8037(4) -1.0341(3) 0.0253(13) Uani 1 1 d . . .
C13 C -0.2235(6) -0.8198(4) -0.8695(4) 0.0311(15) Uani 1 1 d . . .
H13 H -0.1950 -0.8220 -0.8143 0.037 Uiso 1 1 calc R . .
C19 C -0.3347(6) -0.7765(5) -1.1218(3) 0.0312(15) Uani 1 1 d . . .
H19A H -0.3271 -0.6964 -1.1314 0.037 Uiso 1 1 calc R . .
H19B H -0.4286 -0.7980 -1.1296 0.037 Uiso 1 1 calc R . .
O4 O -0.3753(4) -0.6701(3) -0.8501(3) 0.0441(12) Uani 1 1 d . . .
C17 C -0.2379(7) -0.9623(5) -1.1603(4) 0.0375(16) Uani 1 1 d . . .
H17A H -0.1776 -1.0001 -1.1989 0.045 Uiso 1 1 calc R . .
H17B H -0.3270 -0.9955 -1.1664 0.045 Uiso 1 1 calc R . .
C11 C -0.0784(6) -0.9849(5) -0.8913(4) 0.0281(14) Uani 1 1 d . . .
C3AA C -0.3168(6) -0.7358(5) -0.8938(4) 0.0333(15) Uani 1 1 d . . .
C18 C -0.2456(7) -0.8398(5) -1.1834(4) 0.0372(16) Uani 1 1 d . . .
H18A H -0.2826 -0.8323 -1.2391 0.045 Uiso 1 1 calc R . .
H18B H -0.1554 -0.8077 -1.1833 0.045 Uiso 1 1 calc R . .
F1 F 0.0014(4) -0.9621(3) -0.3176(2) 0.0504(10) Uani 1 1 d . . .
F2 F -0.0675(3) -0.9647(2) -0.4437(2) 0.0386(9) Uani 1 1 d . . .
O2 O 0.3652(4) -0.7631(3) -0.4605(2) 0.0288(9) Uani 1 1 d . . .
F3 F 0.0694(4) -1.0920(3) -0.3989(2) 0.0486(11) Uani 1 1 d . . .
C5 C 0.3052(5) -0.8252(4) -0.5212(4) 0.0235(13) Uani 1 1 d . . .
C6 C 0.2055(5) -0.8998(4) -0.5060(3) 0.0196(12) Uani 1 1 d . . .
O3 O 0.0859(4) -1.0515(4) -0.5671(3) 0.0454(12) Uani 1 1 d . . .
C2 C 0.1586(5) -0.9101(5) -0.4203(4) 0.0288(14) Uani 1 1 d . . .
C10 C 0.3679(6) -0.7987(4) -0.6038(3) 0.0264(13) Uani 1 1 d . . .
H10A H 0.4649 -0.7900 -0.5972 0.032 Uiso 1 1 calc R . .
H10B H 0.3316 -0.7284 -0.6246 0.032 Uiso 1 1 calc R . .
O1 O 0.3906(4) -0.7176(3) -0.3275(3) 0.0441(12) Uani 1 1 d . . .
C3 C 0.2173(5) -0.8469(5) -0.3603(4) 0.0287(14) Uani 1 1 d . . .
H3 H 0.1844 -0.8523 -0.3061 0.034 Uiso 1 1 calc R . .
C8 C 0.1931(6) -0.9283(5) -0.6631(3) 0.0336(15) Uani 1 1 d . . .
H8A H 0.1774 -0.9877 -0.7034 0.040 Uiso 1 1 calc R . .
H8B H 0.1363 -0.8650 -0.6783 0.040 Uiso 1 1 calc R . .
C1 C 0.0405(6) -0.9835(5) -0.3969(4) 0.0338(15) Uani 1 1 d . . .
C7 C 0.1532(6) -0.9692(5) -0.5778(4) 0.0308(14) Uani 1 1 d . . .
C9 C 0.3387(6) -0.8933(5) -0.6671(4) 0.0343(15) Uani 1 1 d . . .
H9A H 0.3597 -0.8672 -0.7229 0.041 Uiso 1 1 calc R . .
H9B H 0.3961 -0.9573 -0.6551 0.041 Uiso 1 1 calc R . .
C4 C 0.3262(6) -0.7733(5) -0.3762(4) 0.0338(15) 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
F4 C11 1.355(7) . ?
O5 C14 1.364(6) . ?
O5 C3AA 1.402(7) . ?
F6 C11 1.344(6) . ?
F5 C11 1.312(6) . ?
O6 C16 1.207(6) . ?
C16 C15 1.483(8) . ?
C16 C17 1.515(8) . ?
C15 C14 1.338(7) . ?
C15 C12 1.469(7) . ?
C12 C13 1.353(8) . ?
C12 C11 1.500(8) . ?
C14 C19 1.507(7) . ?
C13 C3AA 1.414(8) . ?
C19 C18 1.523(8) . ?
O4 C3AA 1.200(6) . ?
C17 C18 1.507(8) . ?
F1 C1 1.354(7) . ?
F2 C1 1.323(7) . ?
O2 C5 1.359(6) . ?
O2 C4 1.413(7) . ?
F3 C1 1.324(6) . ?
C5 C6 1.348(7) . ?
C5 C10 1.497(8) . ?
C6 C2 1.457(7) . ?
C6 C7 1.508(7) . ?
O3 C7 1.198(6) . ?
C2 C3 1.352(8) . ?
C2 C1 1.505(8) . ?
C10 C9 1.544(7) . ?
O1 C4 1.206(7) . ?
C3 C4 1.411(8) . ?
C8 C9 1.499(8) . ?
C8 C7 1.506(8) . ?

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
C14 O5 C3AA 120.7(5) . . ?
O6 C16 C15 123.2(5) . . ?
O6 C16 C17 120.4(5) . . ?
C15 C16 C17 116.2(5) . . ?
C14 C15 C12 116.9(5) . . ?
C14 C15 C16 119.3(5) . . ?
C12 C15 C16 123.3(5) . . ?
C13 C12 C15 118.9(5) . . ?
C13 C12 C11 118.8(5) . . ?
C15 C12 C11 122.3(5) . . ?
C15 C14 O5 123.9(5) . . ?
C15 C14 C19 125.6(5) . . ?
O5 C14 C19 110.5(4) . . ?
C12 C13 C3AA 122.7(6) . . ?
C14 C19 C18 109.6(5) . . ?
C18 C17 C16 113.4(5) . . ?
F5 C11 F6 108.7(4) . . ?
F5 C11 F4 105.8(5) . . ?
F6 C11 F4 104.3(5) . . ?
F5 C11 C12 114.3(5) . . ?
F6 C11 C12 112.3(5) . . ?
F4 C11 C12 110.8(5) . . ?
O4 C3AA O5 116.0(5) . . ?
O4 C3AA C13 127.9(6) . . ?
O5 C3AA C13 116.1(5) . . ?
C17 C18 C19 110.4(5) . . ?
C5 O2 C4 121.3(5) . . ?
C6 C5 O2 123.3(5) . . ?
C6 C5 C10 126.9(5) . . ?
O2 C5 C10 109.8(4) . . ?
C5 C6 C2 117.3(5) . . ?
C5 C6 C7 118.3(5) . . ?
C2 C6 C7 124.5(5) . . ?
C3 C2 C6 119.3(5) . . ?
C3 C2 C1 118.5(6) . . ?
C6 C2 C1 122.0(5) . . ?
C5 C10 C9 110.6(5) . . ?
C2 C3 C4 123.0(6) . . ?
C9 C8 C7 112.3(5) . . ?
F2 C1 F3 108.9(5) . . ?
F2 C1 F1 105.7(5) . . ?
F3 C1 F1 105.6(5) . . ?
F2 C1 C2 112.7(5) . . ?
F3 C1 C2 113.2(5) . . ?
F1 C1 C2 110.3(5) . . ?
O3 C7 C8 122.7(5) . . ?
O3 C7 C6 122.0(5) . . ?
C8 C7 C6 115.3(5) . . ?
C8 C9 C10 110.7(5) . . ?
O1 C4 C3 128.9(6) . . ?
O1 C4 O2 115.4(5) . . ?
C3 C4 O2 115.7(5) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.22
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.079
