# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_avv1
_database_code_depnum_ccdc_archive 'CCDC 1047066'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 F3'
_chemical_formula_weight         338.36

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'
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   'P 1 21/n 1'

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                   11.8946(17)
_cell_length_b                   9.7710(6)
_cell_length_c                   14.6459(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.988(9)
_cell_angle_gamma                90.00
_cell_volume                     1695.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    788
_cell_measurement_theta_min      2.6965
_cell_measurement_theta_max      31.8711

_exptl_crystal_description       plates
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.099

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.22741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;



_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2096
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5528
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.1464
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         6.82
_diffrn_reflns_theta_max         23.25
_reflns_number_total             2365
_reflns_number_gt                1447
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;

_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)+(0.0082P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2365
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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

C1 C 0.8282(3) 0.2657(3) 0.1230(2) 0.0197(9) Uani 1 1 d . . .
C2 C 0.7590(3) 0.4008(3) 0.1143(3) 0.0245(9) Uani 1 1 d . . .
H2A H 0.6809 0.3821 0.0933 0.029 Uiso 1 1 calc R . .
H2B H 0.7613 0.4474 0.1730 0.029 Uiso 1 1 calc R . .
C3 C 0.8154(3) 0.4885(3) 0.0437(2) 0.0234(9) Uani 1 1 d . . .
H3 H 0.8806 0.5355 0.0750 0.028 Uiso 1 1 calc R . .
C4 C 0.8887(3) 0.3904(4) -0.1070(3) 0.0271(10) Uani 1 1 d . . .
H4 H 0.8852 0.4749 -0.1363 0.033 Uiso 1 1 calc R . .
C5 C 0.9247(3) 0.2749(4) -0.1512(3) 0.0297(10) Uani 1 1 d . . .
H5 H 0.9462 0.2826 -0.2106 0.036 Uiso 1 1 calc R . .
C6 C 0.9293(3) 0.1474(4) -0.1081(3) 0.0273(10) Uani 1 1 d . . .
H6 H 0.9527 0.0707 -0.1390 0.033 Uiso 1 1 calc R . .
C7 C 0.8988(3) 0.1354(4) -0.0190(3) 0.0253(10) Uani 1 1 d . . .
H7 H 0.9021 0.0509 0.0104 0.030 Uiso 1 1 calc R . .
C8 C 0.8635(3) 0.2506(3) 0.0256(2) 0.0198(9) Uani 1 1 d . . .
C9 C 0.8579(3) 0.3773(3) -0.0180(3) 0.0229(9) Uani 1 1 d . . .
C10 C 0.7537(3) 0.1491(4) 0.1472(3) 0.0285(10) Uani 1 1 d . . .
F1 F 0.70108(18) 0.17190(19) 0.22414(15) 0.0352(6) Uani 1 1 d . . .
F2 F 0.66994(18) 0.12291(19) 0.08105(15) 0.0346(6) Uani 1 1 d . . .
F3 F 0.80950(18) 0.02941(18) 0.16154(15) 0.0347(6) Uani 1 1 d . . .
C11 C 0.9302(3) 0.2765(3) 0.1950(2) 0.0219(9) Uani 1 1 d . . .
C12 C 0.9167(4) 0.3154(3) 0.2854(3) 0.0300(10) Uani 1 1 d . . .
H12 H 0.8447 0.3339 0.3023 0.036 Uiso 1 1 calc R . .
C13 C 1.0080(4) 0.3271(4) 0.3504(3) 0.0313(10) Uani 1 1 d . . .
H13 H 0.9965 0.3525 0.4101 0.038 Uiso 1 1 calc R . .
C14 C 1.1156(4) 0.3012(3) 0.3272(3) 0.0328(11) Uani 1 1 d . . .
H14 H 1.1771 0.3108 0.3705 0.039 Uiso 1 1 calc R . .
C15 C 1.1314(4) 0.2607(4) 0.2382(3) 0.0312(10) Uani 1 1 d . . .
H15 H 1.2036 0.2414 0.2222 0.037 Uiso 1 1 calc R . .
C16 C 1.0401(3) 0.2490(3) 0.1734(3) 0.0255(10) Uani 1 1 d . . .
H16 H 1.0521 0.2221 0.1141 0.031 Uiso 1 1 calc R . .
C17 C 0.7389(3) 0.5937(3) -0.0044(2) 0.0207(9) Uani 1 1 d . . .
C18 C 0.6453(3) 0.5548(4) -0.0618(3) 0.0299(10) Uani 1 1 d . . .
H18 H 0.6297 0.4622 -0.0707 0.036 Uiso 1 1 calc R . .
C19 C 0.5747(3) 0.6510(4) -0.1061(3) 0.0304(10) Uani 1 1 d . . .
H19 H 0.5119 0.6232 -0.1437 0.037 Uiso 1 1 calc R . .
C20 C 0.5983(3) 0.7896(4) -0.0940(3) 0.0291(10) Uani 1 1 d . . .
H20 H 0.5512 0.8548 -0.1236 0.035 Uiso 1 1 calc R . .
C21 C 0.6907(3) 0.8296(4) -0.0386(3) 0.0274(10) Uani 1 1 d . . .
H21 H 0.7068 0.9222 -0.0309 0.033 Uiso 1 1 calc R . .
C22 C 0.7604(3) 0.7328(3) 0.0062(3) 0.0255(9) Uani 1 1 d . . .
H22 H 0.8228 0.7615 0.0441 0.031 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
C1 C10 1.504(5) . ?
C1 C8 1.528(5) . ?
C1 C11 1.540(5) . ?
C1 C2 1.556(4) . ?
C2 C3 1.541(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C17 1.507(5) . ?
C3 C9 1.527(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.387(5) . ?
C4 C9 1.391(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(4) . ?
C10 F2 1.352(4) . ?
C10 F3 1.353(4) . ?
C10 F1 1.354(4) . ?
C11 C16 1.398(5) . ?
C11 C12 1.400(5) . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.389(5) . ?
C17 C22 1.390(4) . ?
C18 C19 1.383(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(5) . ?
C21 H21 0.9300 . ?
C22 H22 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
C10 C1 C8 111.2(3) . . ?
C10 C1 C11 109.6(3) . . ?
C8 C1 C11 112.5(3) . . ?
C10 C1 C2 110.0(3) . . ?
C8 C1 C2 101.1(3) . . ?
C11 C1 C2 112.2(3) . . ?
C3 C2 C1 105.6(3) . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
C17 C3 C9 115.2(3) . . ?
C17 C3 C2 114.4(3) . . ?
C9 C3 C2 100.8(3) . . ?
C17 C3 H3 108.7 . . ?
C9 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C5 C4 C9 118.7(3) . . ?
C5 C4 H4 120.6 . . ?
C9 C4 H4 120.6 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 C1 129.6(3) . . ?
C9 C8 C1 109.6(3) . . ?
C4 C9 C8 120.4(3) . . ?
C4 C9 C3 128.1(3) . . ?
C8 C9 C3 111.5(3) . . ?
F2 C10 F3 105.6(3) . . ?
F2 C10 F1 105.2(3) . . ?
F3 C10 F1 105.6(3) . . ?
F2 C10 C1 112.8(3) . . ?
F3 C10 C1 113.6(3) . . ?
F1 C10 C1 113.3(3) . . ?
C16 C11 C12 116.9(3) . . ?
C16 C11 C1 121.8(3) . . ?
C12 C11 C1 121.2(3) . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 C12 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.2(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 121.5(4) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C18 C17 C22 117.8(3) . . ?
C18 C17 C3 121.1(3) . . ?
C22 C17 C3 121.1(3) . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.2(4) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -150.4(3) . . . . ?
C8 C1 C2 C3 -32.8(3) . . . . ?
C11 C1 C2 C3 87.2(3) . . . . ?
C1 C2 C3 C17 155.8(3) . . . . ?
C1 C2 C3 C9 31.6(3) . . . . ?
C9 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C6 C7 C8 C9 0.3(6) . . . . ?
C6 C7 C8 C1 -178.6(4) . . . . ?
C10 C1 C8 C7 -42.9(5) . . . . ?
C11 C1 C8 C7 80.5(5) . . . . ?
C2 C1 C8 C7 -159.7(4) . . . . ?
C10 C1 C8 C9 138.1(3) . . . . ?
C11 C1 C8 C9 -98.5(3) . . . . ?
C2 C1 C8 C9 21.3(4) . . . . ?
C5 C4 C9 C8 0.1(6) . . . . ?
C5 C4 C9 C3 -179.7(3) . . . . ?
C7 C8 C9 C4 -0.6(5) . . . . ?
C1 C8 C9 C4 178.5(3) . . . . ?
C7 C8 C9 C3 179.3(3) . . . . ?
C1 C8 C9 C3 -1.7(4) . . . . ?
C17 C3 C9 C4 37.3(5) . . . . ?
C2 C3 C9 C4 160.9(4) . . . . ?
C17 C3 C9 C8 -142.5(3) . . . . ?
C2 C3 C9 C8 -18.9(4) . . . . ?
C8 C1 C10 F2 -47.4(4) . . . . ?
C11 C1 C10 F2 -172.4(3) . . . . ?
C2 C1 C10 F2 63.8(4) . . . . ?
C8 C1 C10 F3 72.7(4) . . . . ?
C11 C1 C10 F3 -52.3(4) . . . . ?
C2 C1 C10 F3 -176.1(3) . . . . ?
C8 C1 C10 F1 -166.8(3) . . . . ?
C11 C1 C10 F1 68.2(4) . . . . ?
C2 C1 C10 F1 -55.6(4) . . . . ?
C10 C1 C11 C16 113.0(4) . . . . ?
C8 C1 C11 C16 -11.3(4) . . . . ?
C2 C1 C11 C16 -124.5(3) . . . . ?
C10 C1 C11 C12 -67.4(4) . . . . ?
C8 C1 C11 C12 168.3(3) . . . . ?
C2 C1 C11 C12 55.2(4) . . . . ?
C16 C11 C12 C13 0.4(5) . . . . ?
C1 C11 C12 C13 -179.2(3) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C15 -1.3(5) . . . . ?
C13 C14 C15 C16 1.2(5) . . . . ?
C14 C15 C16 C11 -0.3(5) . . . . ?
C12 C11 C16 C15 -0.5(5) . . . . ?
C1 C11 C16 C15 179.1(3) . . . . ?
C9 C3 C17 C18 51.3(5) . . . . ?
C2 C3 C17 C18 -64.8(4) . . . . ?
C9 C3 C17 C22 -127.8(3) . . . . ?
C2 C3 C17 C22 116.1(4) . . . . ?
C22 C17 C18 C19 -0.9(6) . . . . ?
C3 C17 C18 C19 179.9(3) . . . . ?
C17 C18 C19 C20 0.8(6) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C19 C20 C21 C22 -0.6(6) . . . . ?
C20 C21 C22 C17 0.4(6) . . . . ?
C18 C17 C22 C21 0.3(5) . . . . ?
C3 C17 C22 C21 179.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_avv_24
_database_code_depnum_ccdc_archive 'CCDC 1047315'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_audit_creation_date             2015-01-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 Cl F3'
_chemical_formula_sum            'C26 H24 Cl F3'
_chemical_formula_weight         428.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H24 F3 Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3350(4)
_cell_length_b                   10.6357(5)
_cell_length_c                   11.4303(5)
_cell_angle_alpha                73.153(4)
_cell_angle_beta                 87.926(4)
_cell_angle_gamma                76.728(4)
_cell_volume                     1056.58(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4834
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8340
_cell_measurement_theta_min      4.0370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7883
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         4.043
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -120.0000 120

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega   75.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   60.0000 61

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000   60.0000 81

#__ type_ start__ end____ width___ exp.time_
  7 omega   62.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega  145.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega  129.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
 10 omega  115.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 11 omega  101.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 12 omega   48.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
 13 omega   48.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega  121.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   81.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 16 omega   62.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 17 omega   29.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 18 omega   68.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   92.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
 20 omega   56.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 21 omega  101.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
 22 omega   90.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
 23 omega   42.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 71

#__ type_ start__ end____ width___ exp.time_
 24 omega   55.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 25 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   74.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 27 omega  116.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 56
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1225865000
_diffrn_orient_matrix_UB_12      -0.0788645000
_diffrn_orient_matrix_UB_13      0.0268109000
_diffrn_orient_matrix_UB_21      0.1021645000
_diffrn_orient_matrix_UB_22      -0.1151620000
_diffrn_orient_matrix_UB_23      0.0959492000
_diffrn_orient_matrix_UB_31      -0.0575828000
_diffrn_orient_matrix_UB_32      0.0684922000
_diffrn_orient_matrix_UB_33      0.0996332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3587
_reflns_number_total             3906
_reflns_odcompleteness_completeness 91.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.5885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1099
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C15(H15), C23(H23), C27(H27), C6(H6), C8(H8), C24(H24),
 C26(H26)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C21(H21A,H21B,H21C), C29(H29A,H29B,H29C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl28 Cl 0.31970(5) 0.98574(5) 0.65329(4) 0.03476(15) Uani 1 1 d . . . . .
F12 F 0.01536(11) 0.70258(9) -0.05603(8) 0.0229(2) Uani 1 1 d . . . . .
F11 F 0.16902(11) 0.79320(10) 0.00812(9) 0.0270(2) Uani 1 1 d . . . . .
F13 F -0.05730(11) 0.90047(9) -0.03221(9) 0.0255(2) Uani 1 1 d . . . . .
C18 C -0.34591(18) 0.56064(17) 0.15811(15) 0.0215(3) Uani 1 1 d . . . . .
C19 C -0.20054(18) 0.57464(16) 0.15870(14) 0.0190(3) Uani 1 1 d . . . . .
H19 H -0.1236 0.4998 0.1644 0.023 Uiso 1 1 calc R . . . .
C9 C 0.10167(17) 0.58326(16) 0.21104(15) 0.0187(3) Uani 1 1 d . . . . .
C16 C -0.43210(18) 0.79779(17) 0.14414(14) 0.0219(3) Uani 1 1 d . . . . .
C30 C 0.3161(2) 0.24146(17) 0.19077(17) 0.0273(4) Uani 1 1 d . . . . .
H30A H 0.4169 0.2043 0.2187 0.041 Uiso 1 1 calc GR . . . .
H30B H 0.3110 0.2700 0.1030 0.041 Uiso 1 1 calc GR . . . .
H30C H 0.2601 0.1740 0.2206 0.041 Uiso 1 1 calc GR . . . .
C17 C -0.46000(18) 0.67287(18) 0.15143(15) 0.0223(3) Uani 1 1 d . . . . .
H17 H -0.5569 0.6642 0.1518 0.027 Uiso 1 1 calc R . . . .
C15 C -0.28603(18) 0.80972(16) 0.14204(14) 0.0199(3) Uani 1 1 d . . . . .
H15 H -0.2663 0.8935 0.1346 0.024 Uiso 1 1 calc R . . . .
C23 C 0.05023(18) 0.79986(17) 0.53841(16) 0.0234(3) Uani 1 1 d . . . . .
H23 H -0.0411 0.7801 0.5586 0.028 Uiso 1 1 calc R . . . .
C1 C -0.00883(17) 0.71535(15) 0.14977(14) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.05045(18) 0.70460(17) 0.36003(15) 0.0213(3) Uani 1 1 d . . . . .
H3 H -0.0421 0.6869 0.3968 0.026 Uiso 1 1 calc R . . . .
C2 C 0.01427(18) 0.80408(16) 0.23067(15) 0.0213(3) Uani 1 1 d . . . . .
H2A H 0.0949 0.8474 0.2019 0.026 Uiso 1 1 calc R . . . .
H2B H -0.0743 0.8730 0.2303 0.026 Uiso 1 1 calc R . . . .
C22 C 0.12373(18) 0.76326(17) 0.44116(15) 0.0214(3) Uani 1 1 d . . . . .
C27 C 0.2629(2) 0.78952(19) 0.41557(16) 0.0269(4) Uani 1 1 d . . . . .
H27 H 0.3156 0.7614 0.3535 0.032 Uiso 1 1 calc R . . . .
C14 C -0.16891(17) 0.69843(16) 0.15087(14) 0.0180(3) Uani 1 1 d . . . . .
C21 C -0.5558(2) 0.91936(18) 0.14027(17) 0.0290(4) Uani 1 1 d . . . . .
H21A H -0.6394 0.9156 0.0960 0.044 Uiso 1 1 calc GR . . . .
H21B H -0.5237 1.0003 0.1002 0.044 Uiso 1 1 calc GR . . . .
H21C H -0.5827 0.9192 0.2222 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.02978(18) 0.77750(16) 0.01812(15) 0.0207(3) Uani 1 1 d . . . . .
C29 C 0.2722(2) 0.45277(19) 0.53569(16) 0.0298(4) Uani 1 1 d . . . . .
H29A H 0.3477 0.5011 0.5343 0.045 Uiso 1 1 calc GR . . . .
H29B H 0.3082 0.3596 0.5803 0.045 Uiso 1 1 calc GR . . . .
H29C H 0.1874 0.4910 0.5747 0.045 Uiso 1 1 calc GR . . . .
C20 C -0.3775(2) 0.42590(18) 0.16623(18) 0.0295(4) Uani 1 1 d . . . . .
H20A H -0.2950 0.3717 0.1375 0.044 Uiso 1 1 calc GR . . . .
H20B H -0.4636 0.4390 0.1166 0.044 Uiso 1 1 calc GR . . . .
H20C H -0.3942 0.3811 0.2497 0.044 Uiso 1 1 calc GR . . . .
C7 C 0.25363(18) 0.36086(16) 0.23790(15) 0.0212(3) Uani 1 1 d . . . . .
C25 C 0.24565(19) 0.89606(17) 0.57434(16) 0.0242(4) Uani 1 1 d . . . . .
C4 C 0.13550(17) 0.57816(16) 0.33056(14) 0.0194(3) Uani 1 1 d . . . . .
C6 C 0.28690(18) 0.35721(17) 0.35696(16) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.3500 0.2804 0.4058 0.027 Uiso 1 1 calc R . . . .
C5 C 0.23003(18) 0.46327(17) 0.40620(15) 0.0219(3) Uani 1 1 d . . . . .
C8 C 0.16081(18) 0.47644(16) 0.16372(15) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.1386 0.4821 0.0834 0.024 Uiso 1 1 calc R . . . .
C24 C 0.11088(19) 0.86557(18) 0.60612(16) 0.0258(4) Uani 1 1 d . . . . .
H24 H 0.0614 0.8886 0.6717 0.031 Uiso 1 1 calc R . . . .
C26 C 0.32421(19) 0.85670(19) 0.48064(17) 0.0270(4) Uani 1 1 d . . . . .
H26 H 0.4164 0.8751 0.4618 0.032 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
Cl28 C25 1.7461(17) . ?
F12 C10 1.3492(19) . ?
F11 C10 1.3448(19) . ?
F13 C10 1.3460(18) . ?
C18 C19 1.399(2) . ?
C18 C17 1.391(2) . ?
C18 C20 1.505(2) . ?
C19 H19 0.9300 . ?
C19 C14 1.392(2) . ?
C9 C1 1.531(2) . ?
C9 C4 1.396(2) . ?
C9 C8 1.391(2) . ?
C16 C17 1.390(2) . ?
C16 C15 1.397(2) . ?
C16 C21 1.514(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C30 C7 1.509(2) . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.397(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.390(2) . ?
C23 C24 1.391(2) . ?
C1 C2 1.551(2) . ?
C1 C14 1.545(2) . ?
C1 C10 1.525(2) . ?
C3 H3 0.9800 . ?
C3 C2 1.544(2) . ?
C3 C22 1.515(2) . ?
C3 C4 1.518(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C22 C27 1.394(2) . ?
C27 H27 0.9300 . ?
C27 C26 1.385(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C29 C5 1.511(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C7 C6 1.394(2) . ?
C7 C8 1.393(2) . ?
C25 C24 1.380(3) . ?
C25 C26 1.386(2) . ?
C4 C5 1.403(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.394(2) . ?
C8 H8 0.9300 . ?
C24 H24 0.9300 . ?
C26 H26 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
C19 C18 C20 120.36(15) . . ?
C17 C18 C19 118.80(15) . . ?
C17 C18 C20 120.84(15) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 C18 121.27(15) . . ?
C14 C19 H19 119.4 . . ?
C4 C9 C1 110.12(14) . . ?
C8 C9 C1 128.41(14) . . ?
C8 C9 C4 121.42(15) . . ?
C17 C16 C15 118.70(15) . . ?
C17 C16 C21 121.53(15) . . ?
C15 C16 C21 119.77(15) . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C7 C30 H30A 109.5 . . ?
C7 C30 H30B 109.5 . . ?
C7 C30 H30C 109.5 . . ?
C18 C17 H17 119.3 . . ?
C16 C17 C18 121.34(15) . . ?
C16 C17 H17 119.3 . . ?
C16 C15 H15 119.3 . . ?
C14 C15 C16 121.36(15) . . ?
C14 C15 H15 119.3 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.17(16) . . ?
C24 C23 H23 119.4 . . ?
C9 C1 C2 100.85(12) . . ?
C9 C1 C14 112.87(13) . . ?
C14 C1 C2 112.26(13) . . ?
C10 C1 C9 111.89(13) . . ?
C10 C1 C2 110.12(13) . . ?
C10 C1 C14 108.71(13) . . ?
C2 C3 H3 108.2 . . ?
C22 C3 H3 108.2 . . ?
C22 C3 C2 111.45(13) . . ?
C22 C3 C4 118.85(14) . . ?
C4 C3 H3 108.2 . . ?
C4 C3 C2 101.34(13) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 C1 104.66(12) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C23 C22 C3 120.79(15) . . ?
C23 C22 C27 118.33(15) . . ?
C27 C22 C3 120.77(15) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 C22 121.34(16) . . ?
C26 C27 H27 119.3 . . ?
C19 C14 C15 118.50(15) . . ?
C19 C14 C1 121.67(14) . . ?
C15 C14 C1 119.82(14) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F12 C10 C1 112.74(13) . . ?
F11 C10 F12 106.25(13) . . ?
F11 C10 F13 106.31(13) . . ?
F11 C10 C1 112.81(13) . . ?
F13 C10 F12 105.90(13) . . ?
F13 C10 C1 112.29(13) . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C5 C29 H29A 109.5 . . ?
C5 C29 H29B 109.5 . . ?
C5 C29 H29C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C7 C30 120.59(15) . . ?
C8 C7 C30 120.70(15) . . ?
C8 C7 C6 118.71(15) . . ?
C24 C25 Cl28 119.71(13) . . ?
C24 C25 C26 121.31(15) . . ?
C26 C25 Cl28 118.98(14) . . ?
C9 C4 C3 110.31(14) . . ?
C9 C4 C5 120.12(15) . . ?
C5 C4 C3 129.48(14) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 C7 123.09(15) . . ?
C5 C6 H6 118.5 . . ?
C4 C5 C29 122.46(15) . . ?
C6 C5 C29 120.18(15) . . ?
C6 C5 C4 117.35(15) . . ?
C9 C8 C7 119.29(15) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 118.92(15) . . ?
C25 C24 H24 120.5 . . ?
C27 C26 C25 118.80(16) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?

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
Cl28 C25 C24 C23 176.90(13) . . . . ?
Cl28 C25 C26 C27 -177.87(14) . . . . ?
C18 C19 C14 C15 -0.1(2) . . . . ?
C18 C19 C14 C1 -179.20(14) . . . . ?
C19 C18 C17 C16 0.7(2) . . . . ?
C9 C1 C2 C3 -33.66(15) . . . . ?
C9 C1 C14 C19 -24.7(2) . . . . ?
C9 C1 C14 C15 156.27(14) . . . . ?
C9 C1 C10 F12 67.10(17) . . . . ?
C9 C1 C10 F11 -53.27(17) . . . . ?
C9 C1 C10 F13 -173.38(13) . . . . ?
C9 C4 C5 C29 179.17(15) . . . . ?
C9 C4 C5 C6 0.0(2) . . . . ?
C16 C15 C14 C19 1.7(2) . . . . ?
C16 C15 C14 C1 -179.27(14) . . . . ?
C30 C7 C6 C5 -178.63(16) . . . . ?
C30 C7 C8 C9 178.15(15) . . . . ?
C17 C18 C19 C14 -1.0(2) . . . . ?
C17 C16 C15 C14 -2.0(2) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C23 C22 C27 C26 -3.3(3) . . . . ?
C1 C9 C4 C3 0.50(18) . . . . ?
C1 C9 C4 C5 177.22(14) . . . . ?
C1 C9 C8 C7 -176.07(15) . . . . ?
C3 C22 C27 C26 172.77(16) . . . . ?
C3 C4 C5 C29 -4.8(3) . . . . ?
C3 C4 C5 C6 176.01(16) . . . . ?
C2 C1 C14 C19 -137.86(15) . . . . ?
C2 C1 C14 C15 43.10(19) . . . . ?
C2 C1 C10 F12 178.39(12) . . . . ?
C2 C1 C10 F11 58.02(17) . . . . ?
C2 C1 C10 F13 -62.08(17) . . . . ?
C2 C3 C22 C23 110.40(18) . . . . ?
C2 C3 C22 C27 -65.6(2) . . . . ?
C2 C3 C4 C9 -21.74(17) . . . . ?
C2 C3 C4 C5 161.93(16) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C22 C3 C2 C1 161.52(13) . . . . ?
C22 C3 C4 C9 -144.17(15) . . . . ?
C22 C3 C4 C5 39.5(2) . . . . ?
C22 C27 C26 C25 1.1(3) . . . . ?
C14 C1 C2 C3 86.75(15) . . . . ?
C14 C1 C10 F12 -58.24(17) . . . . ?
C14 C1 C10 F11 -178.61(12) . . . . ?
C14 C1 C10 F13 61.29(16) . . . . ?
C21 C16 C17 C18 -178.34(15) . . . . ?
C21 C16 C15 C14 177.16(15) . . . . ?
C10 C1 C2 C3 -151.98(13) . . . . ?
C10 C1 C14 C19 100.07(16) . . . . ?
C10 C1 C14 C15 -78.97(17) . . . . ?
C20 C18 C19 C14 179.79(15) . . . . ?
C20 C18 C17 C16 179.87(16) . . . . ?
C7 C6 C5 C29 -179.39(16) . . . . ?
C7 C6 C5 C4 -0.2(2) . . . . ?
C4 C9 C1 C2 20.83(17) . . . . ?
C4 C9 C1 C14 -99.13(15) . . . . ?
C4 C9 C1 C10 137.86(14) . . . . ?
C4 C9 C8 C7 1.2(2) . . . . ?
C4 C3 C2 C1 34.10(15) . . . . ?
C4 C3 C22 C23 -132.37(17) . . . . ?
C4 C3 C22 C27 51.6(2) . . . . ?
C6 C7 C8 C9 -1.4(2) . . . . ?
C8 C9 C1 C2 -161.64(16) . . . . ?
C8 C9 C1 C14 78.4(2) . . . . ?
C8 C9 C1 C10 -44.6(2) . . . . ?
C8 C9 C4 C3 -177.23(14) . . . . ?
C8 C9 C4 C5 -0.5(2) . . . . ?
C8 C7 C6 C5 0.9(3) . . . . ?
C24 C23 C22 C3 -173.78(15) . . . . ?
C24 C23 C22 C27 2.3(3) . . . . ?
C24 C25 C26 C27 2.2(3) . . . . ?
C26 C25 C24 C23 -3.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_avv9
_database_code_depnum_ccdc_archive 'CCDC 1047331'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_audit_creation_date             2015-02-04
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H25 F3'
_chemical_formula_sum            'C26 H25 F3'
_chemical_formula_weight         394.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c26 h25 f3'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.1770(4)
_cell_length_b                   10.3545(6)
_cell_length_c                   11.2833(5)
_cell_angle_alpha                76.862(4)
_cell_angle_beta                 87.228(3)
_cell_angle_gamma                75.716(4)
_cell_volume                     1011.79(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8299
_cell_measurement_theta_min      2.6908
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10027
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00   49.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223   19.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega  -93.00   -3.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  -57.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   44.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223   57.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
  4 omega  -87.00  -43.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  178.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   41.00   67.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   -9.00   33.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   89.0000   64.0000 42

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00   66.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  8 omega -100.00  -58.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  178.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega  -76.00  -51.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  -77.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0323350000
_diffrn_orient_matrix_UB_12      0.0336814000
_diffrn_orient_matrix_UB_13      -0.0580890000
_diffrn_orient_matrix_UB_21      -0.0157972000
_diffrn_orient_matrix_UB_22      -0.0616128000
_diffrn_orient_matrix_UB_23      -0.0068445000
_diffrn_orient_matrix_UB_31      -0.0711794000
_diffrn_orient_matrix_UB_32      0.0180629000
_diffrn_orient_matrix_UB_33      0.0273159000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3788
_reflns_number_total             4642
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.5170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1075
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
F15 F 0.66666(10) 0.49722(9) 0.19577(9) 0.0289(2) Uani 1 1 d . . .
F13 F 0.52031(9) 0.38613(9) 0.14160(9) 0.0274(2) Uani 1 1 d . . .
F14 F 0.63729(9) 0.31046(9) 0.31389(8) 0.0250(2) Uani 1 1 d . . .
C4 C 0.79984(14) 0.14089(13) -0.00212(13) 0.0147(3) Uani 1 1 d . . .
C1 C 0.65924(15) -0.04640(14) 0.14683(13) 0.0177(3) Uani 1 1 d . . .
C6 C 0.67999(15) 0.06575(14) 0.18736(13) 0.0172(3) Uani 1 1 d . . .
H6 H 0.6475 0.0779 0.2643 0.021 Uiso 1 1 calc R . .
C9 C 0.78418(15) 0.28893(14) 0.13525(13) 0.0156(3) Uani 1 1 d . . .
C11 C 0.92791(15) 0.26065(14) 0.21173(12) 0.0153(3) Uani 1 1 d . . .
C7 C 0.87294(14) 0.25457(14) -0.06652(13) 0.0151(3) Uani 1 1 d . . .
H7 H 0.9810 0.2247 -0.0485 0.018 Uiso 1 1 calc R . .
C12 C 0.99371(15) 0.13005(14) 0.27893(13) 0.0160(3) Uani 1 1 d . . .
H12 H 0.9498 0.0587 0.2769 0.019 Uiso 1 1 calc R . .
C5 C 0.74951(14) 0.15956(14) 0.11225(13) 0.0150(3) Uani 1 1 d . . .
C3 C 0.78209(15) 0.02848(14) -0.04219(13) 0.0173(3) Uani 1 1 d . . .
H3 H 0.8174 0.0157 -0.1184 0.021 Uiso 1 1 calc R . .
C22 C 0.97677(16) 0.29878(14) -0.27958(14) 0.0199(3) Uani 1 1 d . . .
H22 H 1.0732 0.2663 -0.2463 0.024 Uiso 1 1 calc R . .
C15 C 1.12543(16) 0.34030(15) 0.28519(14) 0.0196(3) Uani 1 1 d . . .
H15 H 1.1696 0.4117 0.2865 0.024 Uiso 1 1 calc R . .
C13 C 1.12377(15) 0.10290(14) 0.34944(13) 0.0170(3) Uani 1 1 d . . .
C1A C 0.57787(16) -0.14418(16) 0.22638(14) 0.0229(3) Uani 1 1 d . . .
H1AA H 0.5502 -0.1157 0.3013 0.034 Uiso 1 1 calc R . .
H1AB H 0.6427 -0.2346 0.2435 0.034 Uiso 1 1 calc R . .
H1AC H 0.4890 -0.1444 0.1849 0.034 Uiso 1 1 calc R . .
C17 C 0.85226(15) 0.29940(13) -0.20291(13) 0.0163(3) Uani 1 1 d . . .
C2 C 0.71125(15) -0.06579(14) 0.03151(13) 0.0177(3) Uani 1 1 d . . .
C8 C 0.80290(16) 0.36782(14) 0.00266(13) 0.0171(3) Uani 1 1 d . . .
H8A H 0.7064 0.4212 -0.0326 0.021 Uiso 1 1 calc R . .
H8B H 0.8688 0.4285 0.0007 0.021 Uiso 1 1 calc R . .
C18 C 0.70878(16) 0.34678(14) -0.25577(14) 0.0191(3) Uani 1 1 d . . .
H18 H 0.6245 0.3474 -0.2066 0.023 Uiso 1 1 calc R . .
C14 C 1.19047(16) 0.20999(15) 0.35235(13) 0.0185(3) Uani 1 1 d . . .
C10 C 0.65278(16) 0.37005(15) 0.19652(14) 0.0204(3) Uani 1 1 d . . .
C16 C 0.99597(16) 0.36624(14) 0.21618(13) 0.0184(3) Uani 1 1 d . . .
H16 H 0.9542 0.4545 0.1726 0.022 Uiso 1 1 calc R . .
C21 C 0.95859(19) 0.34587(15) -0.40456(15) 0.0258(3) Uani 1 1 d . . .
H21 H 1.0426 0.3455 -0.4542 0.031 Uiso 1 1 calc R . .
C13A C 1.18889(17) -0.04053(15) 0.42097(15) 0.0234(3) Uani 1 1 d . . .
H13A H 1.1270 -0.0992 0.4095 0.035 Uiso 1 1 calc R . .
H13B H 1.1923 -0.0403 0.5058 0.035 Uiso 1 1 calc R . .
H13C H 1.2888 -0.0733 0.3931 0.035 Uiso 1 1 calc R . .
C14A C 1.32916(17) 0.18563(17) 0.42925(16) 0.0275(3) Uani 1 1 d . . .
H14A H 1.3594 0.2697 0.4202 0.041 Uiso 1 1 calc R . .
H14B H 1.4091 0.1190 0.4032 0.041 Uiso 1 1 calc R . .
H14C H 1.3071 0.1527 0.5131 0.041 Uiso 1 1 calc R . .
C19 C 0.69086(19) 0.39295(15) -0.38092(15) 0.0259(3) Uani 1 1 d . . .
H19 H 0.5948 0.4237 -0.4149 0.031 Uiso 1 1 calc R . .
C20 C 0.8157(2) 0.39342(16) -0.45577(15) 0.0287(4) Uani 1 1 d . . .
H20 H 0.8034 0.4254 -0.5395 0.034 Uiso 1 1 calc R . .
C2A C 0.69091(17) -0.18721(15) -0.01314(15) 0.0232(3) Uani 1 1 d . . .
H2AA H 0.7428 -0.2701 0.0407 0.035 Uiso 1 1 calc R . .
H2AB H 0.7312 -0.1839 -0.0936 0.035 Uiso 1 1 calc R . .
H2AC H 0.5858 -0.1848 -0.0149 0.035 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
F15 C10 1.3520(16) . ?
F13 C10 1.3475(16) . ?
F14 C10 1.3448(18) . ?
C4 C7 1.5222(18) . ?
C4 C5 1.388(2) . ?
C4 C3 1.3878(19) . ?
C1 C6 1.398(2) . ?
C1 C1A 1.5111(19) . ?
C1 C2 1.404(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.3958(19) . ?
C9 C11 1.5411(18) . ?
C9 C5 1.5295(18) . ?
C9 C8 1.5568(19) . ?
C9 C10 1.5236(19) . ?
C11 C12 1.3941(19) . ?
C11 C16 1.3975(19) . ?
C7 H7 0.9800 . ?
C7 C17 1.5099(19) . ?
C7 C8 1.5470(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.4005(19) . ?
C3 H3 0.9300 . ?
C3 C2 1.400(2) . ?
C22 H22 0.9300 . ?
C22 C17 1.3990(19) . ?
C22 C21 1.387(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.390(2) . ?
C15 C16 1.388(2) . ?
C13 C14 1.400(2) . ?
C13 C13A 1.5093(19) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C17 C18 1.3980(19) . ?
C2 C2A 1.5107(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.388(2) . ?
C14 C14A 1.512(2) . ?
C16 H16 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.386(2) . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.390(2) . ?
C20 H20 0.9300 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 C7 110.81(12) . . ?
C3 C4 C7 128.96(13) . . ?
C3 C4 C5 120.22(13) . . ?
C6 C1 C1A 119.67(13) . . ?
C6 C1 C2 119.81(13) . . ?
C2 C1 C1A 120.50(13) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.95(13) . . ?
C5 C6 H6 120.0 . . ?
C11 C9 C8 111.48(11) . . ?
C5 C9 C11 113.50(11) . . ?
C5 C9 C8 100.98(11) . . ?
C10 C9 C11 109.07(11) . . ?
C10 C9 C5 111.23(11) . . ?
C10 C9 C8 110.41(11) . . ?
C12 C11 C9 121.44(12) . . ?
C12 C11 C16 117.90(13) . . ?
C16 C11 C9 120.66(12) . . ?
C4 C7 H7 108.2 . . ?
C4 C7 C8 101.08(11) . . ?
C17 C7 C4 116.55(11) . . ?
C17 C7 H7 108.2 . . ?
C17 C7 C8 114.02(11) . . ?
C8 C7 H7 108.2 . . ?
C11 C12 H12 118.9 . . ?
C11 C12 C13 122.11(13) . . ?
C13 C12 H12 118.9 . . ?
C4 C5 C6 120.19(13) . . ?
C4 C5 C9 110.04(12) . . ?
C6 C5 C9 129.76(13) . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.30(14) . . ?
C2 C3 H3 119.9 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C17 120.98(14) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C16 C15 C14 121.47(13) . . ?
C12 C13 C13A 119.58(13) . . ?
C14 C13 C12 119.09(13) . . ?
C14 C13 C13A 121.33(13) . . ?
C1 C1A H1AA 109.5 . . ?
C1 C1A H1AB 109.5 . . ?
C1 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C22 C17 C7 120.64(12) . . ?
C18 C17 C7 121.11(12) . . ?
C18 C17 C22 118.22(13) . . ?
C1 C2 C2A 120.44(13) . . ?
C3 C2 C1 119.51(13) . . ?
C3 C2 C2A 120.04(13) . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C7 C8 C9 104.45(11) . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.69(14) . . ?
C19 C18 H18 119.7 . . ?
C15 C14 C13 118.96(13) . . ?
C15 C14 C14A 120.25(13) . . ?
C13 C14 C14A 120.77(13) . . ?
F15 C10 C9 112.59(11) . . ?
F13 C10 F15 106.23(11) . . ?
F13 C10 C9 112.31(12) . . ?
F14 C10 F15 106.01(12) . . ?
F14 C10 F13 106.28(11) . . ?
F14 C10 C9 112.88(12) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.46(13) . . ?
C15 C16 H16 119.8 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.22(15) . . ?
C20 C21 H21 119.9 . . ?
C13 C13A H13A 109.5 . . ?
C13 C13A H13B 109.5 . . ?
C13 C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C14 C14A H14A 109.5 . . ?
C14 C14A H14B 109.5 . . ?
C14 C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.41(14) . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 119.46(14) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C2 C2A H2AA 109.5 . . ?
C2 C2A H2AB 109.5 . . ?
C2 C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 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
C4 C7 C17 C22 -124.77(14) . . . . ?
C4 C7 C17 C18 57.37(17) . . . . ?
C4 C7 C8 C9 33.74(13) . . . . ?
C4 C3 C2 C1 -0.5(2) . . . . ?
C4 C3 C2 C2A 179.40(12) . . . . ?
C1 C6 C5 C4 -0.8(2) . . . . ?
C1 C6 C5 C9 179.77(13) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C6 C1 C2 C2A 179.45(12) . . . . ?
C9 C11 C12 C13 -179.60(12) . . . . ?
C9 C11 C16 C15 180.00(13) . . . . ?
C11 C9 C5 C4 -98.32(13) . . . . ?
C11 C9 C5 C6 81.15(17) . . . . ?
C11 C9 C8 C7 87.17(13) . . . . ?
C11 C9 C10 F15 66.68(15) . . . . ?
C11 C9 C10 F13 -173.45(11) . . . . ?
C11 C9 C10 F14 -53.31(15) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 C13A 179.51(13) . . . . ?
C7 C4 C5 C6 -179.39(12) . . . . ?
C7 C4 C5 C9 0.14(15) . . . . ?
C7 C4 C3 C2 179.85(13) . . . . ?
C7 C17 C18 C19 177.39(13) . . . . ?
C12 C11 C16 C15 0.3(2) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C12 C13 C14 C14A 178.78(13) . . . . ?
C5 C4 C7 C17 -145.61(12) . . . . ?
C5 C4 C7 C8 -21.45(14) . . . . ?
C5 C4 C3 C2 1.01(19) . . . . ?
C5 C9 C11 C12 -16.16(18) . . . . ?
C5 C9 C11 C16 164.20(12) . . . . ?
C5 C9 C8 C7 -33.68(12) . . . . ?
C5 C9 C10 F15 -167.39(12) . . . . ?
C5 C9 C10 F13 -47.52(16) . . . . ?
C5 C9 C10 F14 72.62(15) . . . . ?
C3 C4 C7 C17 35.46(19) . . . . ?
C3 C4 C7 C8 159.62(13) . . . . ?
C3 C4 C5 C6 -0.35(19) . . . . ?
C3 C4 C5 C9 179.17(11) . . . . ?
C22 C17 C18 C19 -0.5(2) . . . . ?
C22 C21 C20 C19 -0.3(2) . . . . ?
C1A C1 C6 C5 -177.35(12) . . . . ?
C1A C1 C2 C3 177.98(12) . . . . ?
C1A C1 C2 C2A -1.9(2) . . . . ?
C17 C7 C8 C9 159.61(11) . . . . ?
C17 C22 C21 C20 -0.6(2) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
C8 C9 C11 C12 -129.37(13) . . . . ?
C8 C9 C11 C16 50.98(17) . . . . ?
C8 C9 C5 C4 21.09(14) . . . . ?
C8 C9 C5 C6 -159.44(13) . . . . ?
C8 C9 C10 F15 -56.13(15) . . . . ?
C8 C9 C10 F13 63.73(15) . . . . ?
C8 C9 C10 F14 -176.13(11) . . . . ?
C8 C7 C17 C22 117.99(14) . . . . ?
C8 C7 C17 C18 -59.87(17) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C14 C15 C16 C11 -0.5(2) . . . . ?
C10 C9 C11 C12 108.45(14) . . . . ?
C10 C9 C11 C16 -71.19(16) . . . . ?
C10 C9 C5 C4 138.24(12) . . . . ?
C10 C9 C5 C6 -42.29(19) . . . . ?
C10 C9 C8 C7 -151.44(11) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C16 C15 C14 C13 0.3(2) . . . . ?
C16 C15 C14 C14A -178.40(14) . . . . ?
C21 C22 C17 C7 -176.94(13) . . . . ?
C21 C22 C17 C18 1.0(2) . . . . ?
C13A C13 C14 C15 -179.69(14) . . . . ?
C13A C13 C14 C14A -1.0(2) . . . . ?

####################################################################### 
# 
# 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_122
_database_code_depnum_ccdc_archive 'CCDC 1047468'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_audit_creation_date             2014-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H16 Cl F3'
_chemical_formula_sum            'C22 H16 Cl F3'
_chemical_formula_weight         372.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 h10 F3 P Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.5842(4)
_cell_length_b                   9.2772(3)
_cell_length_c                   17.8208(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.018(3)
_cell_angle_gamma                90.00
_cell_volume                     1749.87(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3108
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4450
_cell_measurement_theta_min      4.9630
_exptl_absorpt_coefficient_mu    2.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7629
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         4.18
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   38.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   38.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   38.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega   60.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   55.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287 -178.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega  140.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   49.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   78.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega  118.00  143.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   49.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 12 omega   95.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   78.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega  131.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 15 omega  117.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -30.0000 56

#__ type_ start__ end____ width___ exp.time_
 16 omega   30.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 17 omega   83.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega   98.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 19 omega   84.00  142.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 20 omega   70.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   49.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  127.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
 23 omega   88.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
 24 omega   37.00   66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 25 omega   62.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega  102.00  127.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   94.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 12
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0858542000
_diffrn_orient_matrix_UB_12      0.0106543000
_diffrn_orient_matrix_UB_13      0.0696091000
_diffrn_orient_matrix_UB_21      0.0639288000
_diffrn_orient_matrix_UB_22      0.1347522000
_diffrn_orient_matrix_UB_23      -0.0333606000
_diffrn_orient_matrix_UB_31      -0.0986156000
_diffrn_orient_matrix_UB_32      0.0964792000
_diffrn_orient_matrix_UB_33      0.0389169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2592
_reflns_number_total             3031
_reflns_odcompleteness_completeness 88.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.5078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0983
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C6(H6), C16(H16), C22(H22), C2(H2), C15(H15), C23(H23),
 C18(H18), C24(H24), C26(H26), C25(H25), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl20 Cl 0.06395(4) 0.30935(5) 0.08152(2) 0.02839(14) Uani 1 d . . .
F11 F 0.16909(11) -0.43735(12) -0.17990(6) 0.0303(3) Uani 1 d . . .
F13 F 0.07526(11) -0.38637(12) -0.28384(7) 0.0328(3) Uani 1 d . . .
F12 F 0.25300(11) -0.49986(11) -0.28507(6) 0.0306(3) Uani 1 d . . .
C19 C 0.19600(17) 0.21015(19) -0.12265(10) 0.0232(4) Uani 1 d . . .
H19 H 0.2131 0.2582 -0.1673 0.028 Uiso 1 calc . . R
C4 C 0.38337(16) -0.11907(18) -0.16370(9) 0.0198(4) Uani 1 d . . .
C3 C 0.48369(17) -0.09183(19) -0.11632(10) 0.0232(4) Uani 1 d . . .
H3 H 0.4889 -0.0048 -0.0906 0.028 Uiso 1 calc . . R
C10 C 0.19001(18) -0.39292(19) -0.25106(10) 0.0238(4) Uani 1 d . . .
C6 C 0.46755(17) -0.3551(2) -0.19302(10) 0.0230(4) Uani 1 d . . .
H6 H 0.4619 -0.4426 -0.2183 0.028 Uiso 1 calc . . R
C14 C 0.21990(16) 0.06301(19) -0.11734(10) 0.0203(3) Uani 1 d . . .
C7 C 0.27243(16) -0.02130(18) -0.18293(9) 0.0202(4) Uani 1 d . . .
H7 H 0.2990 0.0466 -0.2220 0.024 Uiso 1 calc . . R
C16 C 0.14360(17) 0.0676(2) 0.01119(10) 0.0230(4) Uani 1 d . . .
H16 H 0.1256 0.0200 0.0558 0.028 Uiso 1 calc . . R
C22 C 0.20006(18) -0.17672(19) -0.38685(10) 0.0239(4) Uani 1 d . . .
H22 H 0.1161 -0.1757 -0.3715 0.029 Uiso 1 calc . . R
C2 C 0.57705(18) -0.1961(2) -0.10743(10) 0.0261(4) Uani 1 d . . .
H2 H 0.6455 -0.1783 -0.0760 0.031 Uiso 1 calc . . R
C15 C 0.19271(17) -0.00674(19) -0.04965(10) 0.0234(4) Uani 1 d . . .
H15 H 0.2079 -0.1051 -0.0454 0.028 Uiso 1 calc . . R
C5 C 0.37459(16) -0.24960(18) -0.20239(9) 0.0193(4) Uani 1 d . . .
C23 C 0.22997(19) -0.14165(19) -0.46048(10) 0.0267(4) Uani 1 d . . .
H23 H 0.1659 -0.1171 -0.4938 0.032 Uiso 1 calc . . R
C18 C 0.14684(18) 0.28651(19) -0.06199(10) 0.0246(4) Uani 1 d . . .
H18 H 0.1310 0.3848 -0.0660 0.029 Uiso 1 calc . . R
C9 C 0.25994(17) -0.24908(18) -0.25353(9) 0.0199(4) Uani 1 d . . .
C24 C 0.3544(2) -0.14297(19) -0.48470(10) 0.0268(4) Uani 1 d . . .
H24 H 0.3741 -0.1192 -0.5340 0.032 Uiso 1 calc . . R
C17 C 0.12198(17) 0.2142(2) 0.00414(10) 0.0228(4) Uani 1 d . . .
C21 C 0.29430(17) -0.21336(18) -0.33563(9) 0.0196(4) Uani 1 d . . .
C26 C 0.41956(17) -0.21524(18) -0.36054(10) 0.0220(4) Uani 1 d . . .
H26 H 0.4839 -0.2401 -0.3274 0.026 Uiso 1 calc . . R
C25 C 0.44871(19) -0.18013(19) -0.43462(10) 0.0256(4) Uani 1 d . . .
H25 H 0.5324 -0.1817 -0.4505 0.031 Uiso 1 calc . . R
C8 C 0.17702(17) -0.12928(19) -0.21732(10) 0.0221(4) Uani 1 d . . .
H8A H 0.1249 -0.0825 -0.2549 0.027 Uiso 1 calc . . R
H8B H 0.1227 -0.1694 -0.1788 0.027 Uiso 1 calc . . R
C1 C 0.56861(18) -0.3270(2) -0.14529(10) 0.0261(4) Uani 1 d . . .
H1 H 0.6311 -0.3963 -0.1386 0.031 Uiso 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
Cl20 C17 1.7490(17) . ?
F11 C10 1.352(2) . ?
F13 C10 1.349(2) . ?
F12 C10 1.340(2) . ?
C19 C14 1.392(2) . ?
C19 C18 1.393(3) . ?
C4 C3 1.380(3) . ?
C4 C7 1.523(2) . ?
C4 C5 1.397(2) . ?
C3 C2 1.392(3) . ?
C10 C9 1.527(2) . ?
C6 C5 1.397(2) . ?
C6 C1 1.391(3) . ?
C14 C7 1.512(2) . ?
C14 C15 1.399(2) . ?
C7 C8 1.549(2) . ?
C16 C15 1.386(3) . ?
C16 C17 1.384(3) . ?
C22 C23 1.388(3) . ?
C22 C21 1.394(3) . ?
C2 C1 1.392(3) . ?
C5 C9 1.517(3) . ?
C23 C24 1.386(3) . ?
C18 C17 1.382(3) . ?
C9 C21 1.544(2) . ?
C9 C8 1.556(2) . ?
C24 C25 1.383(3) . ?
C21 C26 1.398(2) . ?
C26 C25 1.394(2) . ?

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 C19 C18 120.92(17) . . ?
C3 C4 C7 128.45(16) . . ?
C3 C4 C5 120.80(16) . . ?
C5 C4 C7 110.75(15) . . ?
C4 C3 C2 119.24(17) . . ?
F11 C10 C9 111.91(15) . . ?
F13 C10 F11 105.80(14) . . ?
F13 C10 C9 112.61(15) . . ?
F12 C10 F11 106.27(14) . . ?
F12 C10 F13 106.59(15) . . ?
F12 C10 C9 113.13(14) . . ?
C1 C6 C5 118.88(17) . . ?
C19 C14 C7 121.44(15) . . ?
C19 C14 C15 118.36(16) . . ?
C15 C14 C7 120.20(16) . . ?
C4 C7 C8 101.91(14) . . ?
C14 C7 C4 114.70(14) . . ?
C14 C7 C8 113.61(14) . . ?
C17 C16 C15 118.68(16) . . ?
C23 C22 C21 120.83(17) . . ?
C1 C2 C3 120.38(18) . . ?
C16 C15 C14 121.43(16) . . ?
C4 C5 C6 120.09(17) . . ?
C4 C5 C9 110.29(15) . . ?
C6 C5 C9 129.55(16) . . ?
C24 C23 C22 120.62(18) . . ?
C17 C18 C19 119.08(16) . . ?
C10 C9 C21 109.23(14) . . ?
C10 C9 C8 109.80(14) . . ?
C5 C9 C10 111.56(14) . . ?
C5 C9 C21 112.42(14) . . ?
C5 C9 C8 101.78(13) . . ?
C21 C9 C8 111.89(14) . . ?
C25 C24 C23 119.15(16) . . ?
C16 C17 Cl20 118.85(14) . . ?
C18 C17 Cl20 119.61(14) . . ?
C18 C17 C16 121.53(16) . . ?
C22 C21 C9 120.28(16) . . ?
C22 C21 C26 118.27(16) . . ?
C26 C21 C9 121.45(16) . . ?
C25 C26 C21 120.51(17) . . ?
C24 C25 C26 120.63(17) . . ?
C7 C8 C9 104.97(14) . . ?
C6 C1 C2 120.61(17) . . ?

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
F11 C10 C9 C5 48.62(19) . . . . ?
F11 C10 C9 C21 173.52(14) . . . . ?
F11 C10 C9 C8 -63.44(19) . . . . ?
F13 C10 C9 C5 167.66(14) . . . . ?
F13 C10 C9 C21 -67.44(18) . . . . ?
F13 C10 C9 C8 55.60(19) . . . . ?
F12 C10 C9 C5 -71.40(18) . . . . ?
F12 C10 C9 C21 53.5(2) . . . . ?
F12 C10 C9 C8 176.54(14) . . . . ?
C19 C14 C7 C4 132.32(18) . . . . ?
C19 C14 C7 C8 -111.00(19) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C19 C18 C17 Cl20 178.42(14) . . . . ?
C19 C18 C17 C16 -0.6(3) . . . . ?
C4 C3 C2 C1 -0.7(3) . . . . ?
C4 C7 C8 C9 -29.80(16) . . . . ?
C4 C5 C9 C10 -138.02(14) . . . . ?
C4 C5 C9 C21 98.88(16) . . . . ?
C4 C5 C9 C8 -20.99(17) . . . . ?
C3 C4 C7 C14 -40.1(2) . . . . ?
C3 C4 C7 C8 -163.27(16) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C5 C9 -176.98(14) . . . . ?
C3 C2 C1 C6 0.6(3) . . . . ?
C10 C9 C21 C22 69.9(2) . . . . ?
C10 C9 C21 C26 -110.80(18) . . . . ?
C10 C9 C8 C7 149.42(14) . . . . ?
C6 C5 C9 C10 44.9(2) . . . . ?
C6 C5 C9 C21 -78.2(2) . . . . ?
C6 C5 C9 C8 161.91(16) . . . . ?
C14 C19 C18 C17 0.1(3) . . . . ?
C14 C7 C8 C9 -153.73(14) . . . . ?
C7 C4 C3 C2 -178.98(16) . . . . ?
C7 C4 C5 C6 179.73(14) . . . . ?
C7 C4 C5 C9 2.31(18) . . . . ?
C7 C14 C15 C16 -179.51(16) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C15 C14 C7 C4 -48.4(2) . . . . ?
C15 C14 C7 C8 68.2(2) . . . . ?
C15 C16 C17 Cl20 -178.34(14) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C5 C4 C3 C2 0.2(2) . . . . ?
C5 C4 C7 C14 140.70(15) . . . . ?
C5 C4 C7 C8 17.51(17) . . . . ?
C5 C6 C1 C2 0.0(3) . . . . ?
C5 C9 C21 C22 -165.75(15) . . . . ?
C5 C9 C21 C26 13.6(2) . . . . ?
C5 C9 C8 C7 31.12(16) . . . . ?
C23 C22 C21 C9 178.75(16) . . . . ?
C23 C22 C21 C26 -0.6(3) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C18 C19 C14 C7 179.59(16) . . . . ?
C18 C19 C14 C15 0.3(3) . . . . ?
C9 C21 C26 C25 -178.85(15) . . . . ?
C17 C16 C15 C14 -0.3(3) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C21 C9 C8 C7 -89.11(17) . . . . ?
C21 C26 C25 C24 0.0(3) . . . . ?
C8 C9 C21 C22 -51.9(2) . . . . ?
C8 C9 C21 C26 127.40(17) . . . . ?
C1 C6 C5 C4 -0.5(2) . . . . ?
C1 C6 C5 C9 176.32(16) . . . . ?

####################################################################### 
# 
# 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_avv20
_database_code_depnum_ccdc_archive 'CCDC 1047593'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 Cl F3 O4'
_chemical_formula_weight         492.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   8.9801(3)
_cell_length_b                   11.8644(5)
_cell_length_c                   12.6622(6)
_cell_angle_alpha                64.998(4)
_cell_angle_beta                 71.043(4)
_cell_angle_gamma                80.660(3)
_cell_volume                     1155.85(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8041
_cell_measurement_theta_min      4.0110
_cell_measurement_theta_max      76.1290

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    1.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19213
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.02
_diffrn_reflns_theta_max         76.31
_reflns_number_total             4787
_reflns_number_gt                4052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?

_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_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)+(0.0151P)²+1.9000P] 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         4787
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
Cl26 Cl 0.86567(7) 0.76614(6) 0.01769(6) 0.03052(15) Uani 1 1 d . . .
F14 F 0.52573(16) 0.16453(13) -0.03295(13) 0.0290(3) Uani 1 1 d . . .
F13 F 0.58197(17) 0.07659(13) -0.15994(14) 0.0278(3) Uani 1 1 d . . .
F12 F 0.73135(16) 0.04451(13) -0.04569(13) 0.0272(3) Uani 1 1 d . . .
O31 O 1.22437(19) 0.07939(16) -0.54328(15) 0.0243(4) Uani 1 1 d . . .
O27 O 0.37754(19) 0.67442(15) -0.39882(16) 0.0249(4) Uani 1 1 d . . .
O28 O 0.29586(18) 0.47102(15) -0.38651(15) 0.0215(3) Uani 1 1 d . . .
O33 O 1.2428(2) 0.01474(17) -0.32544(16) 0.0262(4) Uani 1 1 d . . .
C20 C 0.8422(2) 0.5177(2) -0.1650(2) 0.0184(4) Uani 1 1 d . . .
C11 C 0.8688(2) 0.2024(2) -0.3039(2) 0.0175(4) Uani 1 1 d . . .
C6 C 0.6361(2) 0.3519(2) -0.2638(2) 0.0173(4) Uani 1 1 d . . .
C18 C 1.1135(3) 0.0870(2) -0.3509(2) 0.0193(4) Uani 1 1 d . . .
C23 C 0.8598(3) 0.6653(2) -0.0485(2) 0.0217(5) Uani 1 1 d . . .
C15 C 0.9795(3) 0.1997(2) -0.5043(2) 0.0204(4) Uani 1 1 d . . .
H15 H 0.9729 0.2247 -0.5829 0.024 Uiso 1 1 calc R . .
C4 C 0.5990(3) 0.5733(2) -0.3171(2) 0.0199(4) Uani 1 1 d . . .
H4 H 0.6304 0.6471 -0.3227 0.024 Uiso 1 1 calc R . .
C17 C 0.9958(3) 0.1244(2) -0.2690(2) 0.0183(4) Uani 1 1 d . . .
H17 H 1.0005 0.0977 -0.1897 0.022 Uiso 1 1 calc R . .
C5 C 0.6821(2) 0.4618(2) -0.2721(2) 0.0183(4) Uani 1 1 d . . .
C19 C 1.1044(3) 0.1235(2) -0.4703(2) 0.0190(4) Uani 1 1 d . . .
C24 C 0.9928(3) 0.6472(2) -0.1339(2) 0.0220(5) Uani 1 1 d . . .
H24 H 1.0871 0.6836 -0.1521 0.026 Uiso 1 1 calc R . .
C1 C 0.5064(3) 0.3502(2) -0.3015(2) 0.0188(4) Uani 1 1 d . . .
H1 H 0.4765 0.2763 -0.2966 0.023 Uiso 1 1 calc R . .
C2 C 0.4233(2) 0.4602(2) -0.3461(2) 0.0182(4) Uani 1 1 d . . .
C3 C 0.4690(3) 0.5726(2) -0.3534(2) 0.0201(4) Uani 1 1 d . . .
C7 C 0.8286(3) 0.4402(2) -0.2303(2) 0.0192(4) Uani 1 1 d . . .
H7 H 0.9214 0.4536 -0.3011 0.023 Uiso 1 1 calc R . .
C8 C 0.8191(3) 0.2998(2) -0.1491(2) 0.0209(5) Uani 1 1 d . . .
H8A H 0.7545 0.2856 -0.0669 0.025 Uiso 1 1 calc R . .
H8B H 0.9233 0.2631 -0.1466 0.025 Uiso 1 1 calc R . .
C16 C 0.8626(3) 0.2396(2) -0.4214(2) 0.0191(4) Uani 1 1 d . . .
H16 H 0.7801 0.2916 -0.4459 0.023 Uiso 1 1 calc R . .
C9 C 0.7430(3) 0.2436(2) -0.2099(2) 0.0182(4) Uani 1 1 d . . .
C10 C 0.6460(3) 0.1325(2) -0.1125(2) 0.0213(5) Uani 1 1 d . . .
C29 C 0.2420(3) 0.3586(2) -0.3749(2) 0.0224(5) Uani 1 1 d . . .
H29A H 0.3272 0.3172 -0.4151 0.034 Uiso 1 1 calc R . .
H29B H 0.1578 0.3775 -0.4116 0.034 Uiso 1 1 calc R . .
H29C H 0.2047 0.3054 -0.2904 0.034 Uiso 1 1 calc R . .
C34 C 1.2597(3) -0.0189(3) -0.2076(2) 0.0295(5) Uani 1 1 d . . .
H34A H 1.3564 -0.0661 -0.2017 0.044 Uiso 1 1 calc R . .
H34B H 1.1727 -0.0683 -0.1470 0.044 Uiso 1 1 calc R . .
H34C H 1.2615 0.0550 -0.1948 0.044 Uiso 1 1 calc R . .
C25 C 0.9822(3) 0.5728(2) -0.1921(2) 0.0197(4) Uani 1 1 d . . .
H25 H 1.0704 0.5601 -0.2499 0.024 Uiso 1 1 calc R . .
C21 C 0.7128(3) 0.5341(2) -0.0749(2) 0.0265(5) Uani 1 1 d . . .
H21 H 0.6198 0.4947 -0.0540 0.032 Uiso 1 1 calc R . .
C32 C 1.2155(3) 0.1087(2) -0.6627(2) 0.0253(5) Uani 1 1 d . . .
H32A H 1.2211 0.1970 -0.7082 0.038 Uiso 1 1 calc R . .
H32B H 1.1178 0.0807 -0.6572 0.038 Uiso 1 1 calc R . .
H32C H 1.3017 0.0679 -0.7028 0.038 Uiso 1 1 calc R . .
C22 C 0.7193(3) 0.6077(2) -0.0154(2) 0.0260(5) Uani 1 1 d . . .
H22 H 0.6323 0.6180 0.0446 0.031 Uiso 1 1 calc R . .
C30 C 0.4162(3) 0.7901(2) -0.4055(3) 0.0323(6) Uani 1 1 d . . .
H30A H 0.5200 0.8125 -0.4598 0.048 Uiso 1 1 calc R . .
H30B H 0.4131 0.7817 -0.3261 0.048 Uiso 1 1 calc R . .
H30C H 0.3414 0.8537 -0.4352 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
Cl26 C23 1.742(2) . ?
F14 C10 1.345(3) . ?
F13 C10 1.348(3) . ?
F12 C10 1.345(3) . ?
O31 C19 1.367(3) . ?
O31 C32 1.427(3) . ?
O27 C3 1.364(3) . ?
O27 C30 1.431(3) . ?
O28 C2 1.366(3) . ?
O28 C29 1.426(3) . ?
O33 C18 1.369(3) . ?
O33 C34 1.425(3) . ?
C20 C25 1.386(3) . ?
C20 C21 1.394(3) . ?
C20 C7 1.513(3) . ?
C11 C16 1.379(3) . ?
C11 C17 1.411(3) . ?
C11 C9 1.539(3) . ?
C6 C5 1.382(3) . ?
C6 C1 1.401(3) . ?
C6 C9 1.524(3) . ?
C18 C17 1.384(3) . ?
C18 C19 1.412(3) . ?
C23 C24 1.384(3) . ?
C23 C22 1.389(3) . ?
C15 C19 1.384(3) . ?
C15 C16 1.404(3) . ?
C15 H15 0.9300 . ?
C4 C3 1.390(3) . ?
C4 C5 1.397(3) . ?
C4 H4 0.9300 . ?
C17 H17 0.9300 . ?
C5 C7 1.519(3) . ?
C24 C25 1.397(3) . ?
C24 H24 0.9300 . ?
C1 C2 1.383(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.415(3) . ?
C7 C8 1.543(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.558(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C16 H16 0.9300 . ?
C9 C10 1.523(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C25 H25 0.9300 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C22 H22 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O31 C32 117.16(18) . . ?
C3 O27 C30 117.06(19) . . ?
C2 O28 C29 116.47(18) . . ?
C18 O33 C34 117.06(18) . . ?
C25 C20 C21 118.6(2) . . ?
C25 C20 C7 121.33(19) . . ?
C21 C20 C7 120.0(2) . . ?
C16 C11 C17 118.7(2) . . ?
C16 C11 C9 122.4(2) . . ?
C17 C11 C9 118.9(2) . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 C9 110.63(19) . . ?
C1 C6 C9 128.6(2) . . ?
O33 C18 C17 124.6(2) . . ?
O33 C18 C19 115.54(19) . . ?
C17 C18 C19 119.8(2) . . ?
C24 C23 C22 122.2(2) . . ?
C24 C23 Cl26 119.46(18) . . ?
C22 C23 Cl26 118.35(18) . . ?
C19 C15 C16 120.7(2) . . ?
C19 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C18 C17 C11 121.1(2) . . ?
C18 C17 H17 119.5 . . ?
C11 C17 H17 119.5 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 C7 110.78(19) . . ?
C4 C5 C7 128.5(2) . . ?
O31 C19 C15 125.6(2) . . ?
O31 C19 C18 115.3(2) . . ?
C15 C19 C18 119.1(2) . . ?
C23 C24 C25 118.5(2) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C2 C1 C6 119.0(2) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
O28 C2 C1 124.6(2) . . ?
O28 C2 C3 115.0(2) . . ?
C1 C2 C3 120.4(2) . . ?
O27 C3 C4 125.2(2) . . ?
O27 C3 C2 114.7(2) . . ?
C4 C3 C2 120.1(2) . . ?
C20 C7 C5 117.06(18) . . ?
C20 C7 C8 112.75(19) . . ?
C5 C7 C8 100.97(18) . . ?
C20 C7 H7 108.5 . . ?
C5 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C7 C8 C9 104.87(18) . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C9 C8 H8B 110.8 . . ?
H8A C8 H8B 108.8 . . ?
C11 C16 C15 120.7(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C10 C9 C6 110.63(18) . . ?
C10 C9 C11 109.49(18) . . ?
C6 C9 C11 114.52(18) . . ?
C10 C9 C8 109.46(19) . . ?
C6 C9 C8 100.97(17) . . ?
C11 C9 C8 111.47(18) . . ?
F12 C10 F14 105.94(19) . . ?
F12 C10 F13 106.72(18) . . ?
F14 C10 F13 106.38(18) . . ?
F12 C10 C9 112.64(19) . . ?
F14 C10 C9 112.35(18) . . ?
F13 C10 C9 112.33(19) . . ?
O28 C29 H29A 109.5 . . ?
O28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O33 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C20 C25 C24 121.1(2) . . ?
C20 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C22 C21 C20 121.7(2) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C23 C22 C21 117.8(2) . . ?
C23 C22 H22 121.1 . . ?
C21 C22 H22 121.1 . . ?
O27 C30 H30A 109.5 . . ?
O27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
C34 O33 C18 C17 -3.0(3) . . . . ?
C34 O33 C18 C19 177.1(2) . . . . ?
O33 C18 C17 C11 177.9(2) . . . . ?
C19 C18 C17 C11 -2.2(3) . . . . ?
C16 C11 C17 C18 0.9(3) . . . . ?
C9 C11 C17 C18 -178.7(2) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C9 C6 C5 C4 -178.9(2) . . . . ?
C1 C6 C5 C7 -177.86(19) . . . . ?
C9 C6 C5 C7 2.6(2) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C7 178.3(2) . . . . ?
C32 O31 C19 C15 -3.7(3) . . . . ?
C32 O31 C19 C18 176.8(2) . . . . ?
C16 C15 C19 O31 -179.9(2) . . . . ?
C16 C15 C19 C18 -0.4(3) . . . . ?
O33 C18 C19 O31 1.4(3) . . . . ?
C17 C18 C19 O31 -178.5(2) . . . . ?
O33 C18 C19 C15 -178.1(2) . . . . ?
C17 C18 C19 C15 1.9(3) . . . . ?
C22 C23 C24 C25 2.9(4) . . . . ?
Cl26 C23 C24 C25 -175.53(18) . . . . ?
C5 C6 C1 C2 -0.7(3) . . . . ?
C9 C6 C1 C2 178.7(2) . . . . ?
C29 O28 C2 C1 3.5(3) . . . . ?
C29 O28 C2 C3 -177.05(19) . . . . ?
C6 C1 C2 O28 179.4(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C30 O27 C3 C4 -2.2(3) . . . . ?
C30 O27 C3 C2 178.5(2) . . . . ?
C5 C4 C3 O27 180.0(2) . . . . ?
C5 C4 C3 C2 -0.8(3) . . . . ?
O28 C2 C3 O27 0.6(3) . . . . ?
C1 C2 C3 O27 -179.9(2) . . . . ?
O28 C2 C3 C4 -178.7(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C25 C20 C7 C5 -135.8(2) . . . . ?
C21 C20 C7 C5 44.8(3) . . . . ?
C25 C20 C7 C8 107.7(2) . . . . ?
C21 C20 C7 C8 -71.7(3) . . . . ?
C6 C5 C7 C20 -145.4(2) . . . . ?
C4 C5 C7 C20 36.3(3) . . . . ?
C6 C5 C7 C8 -22.6(2) . . . . ?
C4 C5 C7 C8 159.0(2) . . . . ?
C20 C7 C8 C9 158.91(17) . . . . ?
C5 C7 C8 C9 33.2(2) . . . . ?
C17 C11 C16 C15 0.6(3) . . . . ?
C9 C11 C16 C15 -179.8(2) . . . . ?
C19 C15 C16 C11 -0.9(3) . . . . ?
C5 C6 C9 C10 134.2(2) . . . . ?
C1 C6 C9 C10 -45.3(3) . . . . ?
C5 C6 C9 C11 -101.5(2) . . . . ?
C1 C6 C9 C11 79.0(3) . . . . ?
C5 C6 C9 C8 18.4(2) . . . . ?
C1 C6 C9 C8 -161.1(2) . . . . ?
C16 C11 C9 C10 110.5(2) . . . . ?
C17 C11 C9 C10 -69.9(3) . . . . ?
C16 C11 C9 C6 -14.4(3) . . . . ?
C17 C11 C9 C6 165.15(19) . . . . ?
C16 C11 C9 C8 -128.2(2) . . . . ?
C17 C11 C9 C8 51.3(3) . . . . ?
C7 C8 C9 C10 -148.48(17) . . . . ?
C7 C8 C9 C6 -31.8(2) . . . . ?
C7 C8 C9 C11 90.2(2) . . . . ?
C6 C9 C10 F12 -167.39(18) . . . . ?
C11 C9 C10 F12 65.5(2) . . . . ?
C8 C9 C10 F12 -57.0(2) . . . . ?
C6 C9 C10 F14 -47.8(3) . . . . ?
C11 C9 C10 F14 -174.98(18) . . . . ?
C8 C9 C10 F14 62.6(2) . . . . ?
C6 C9 C10 F13 72.1(2) . . . . ?
C11 C9 C10 F13 -55.1(2) . . . . ?
C8 C9 C10 F13 -177.54(17) . . . . ?
C21 C20 C25 C24 -2.4(4) . . . . ?
C7 C20 C25 C24 178.2(2) . . . . ?
C23 C24 C25 C20 -0.3(3) . . . . ?
C25 C20 C21 C22 2.5(4) . . . . ?
C7 C20 C21 C22 -178.0(2) . . . . ?
C24 C23 C22 C21 -2.8(4) . . . . ?
Cl26 C23 C22 C21 175.7(2) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        76.31
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_avv_23
_database_code_depnum_ccdc_archive 'CCDC 1048565'
_audit_update_record             
;
2015-02-10 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_audit_creation_date             2015-02-10
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H21 F3 O Si'
_chemical_formula_sum            'C19 H21 F3 O Si'
_chemical_formula_weight         350.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c16 h14 O2 Si1 f6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.1449(3)
_cell_length_b                   7.95800(16)
_cell_length_c                   16.5726(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.274(2)
_cell_angle_gamma                90.00
_cell_volume                     1841.11(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10582
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0520
_cell_measurement_theta_min      5.4270
_exptl_absorpt_coefficient_mu    1.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22291
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9947
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00  -23.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -86.00  -36.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -178.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   36.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega  -39.00  -11.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega -119.00  -54.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
  6 omega -113.00  -88.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -77.00   33.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   86.0000   40.0000 110

#__ type_ start__ end____ width___ exp.time_
  8 omega   91.00  117.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   60.00  129.00   1.0000    2.4900
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
 10 omega   57.00   83.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  135.00  164.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega   84.00  109.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00   71.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   97.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 15 omega  102.00  147.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   77.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega  100.00  139.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
 18 omega   57.00   83.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   55.00  105.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
 20 omega   80.00  113.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 21 omega  105.00  135.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 22 omega   85.00  173.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
 23 omega   90.00  115.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega  152.00  177.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   86.00  112.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   54.00   86.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 27 omega   48.00  103.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
 28 omega  107.00  133.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   38.00   71.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 30 omega   62.00   88.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega  107.00  143.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 32 omega   44.00  110.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 66

#__ type_ start__ end____ width___ exp.time_
 33 omega   75.00  101.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   54.00  109.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 35 omega   96.00  132.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
 36 omega   38.00   66.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 37 omega  110.00  147.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 38 omega   51.00   78.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 39 omega   85.00  176.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
 40 omega   58.00   94.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 41 omega  101.00  126.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   59.00   95.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 43 omega   30.00   61.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 44 omega   73.00   98.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 45 omega   54.00  108.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
 46 omega   90.00  115.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 47 omega   52.00  109.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
 48 omega   63.00  103.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 49 omega  109.00  139.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 50 omega  149.00  176.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 51 omega   98.00  124.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 52 omega  137.00  164.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 53 omega   85.00  110.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 54 omega   80.00  105.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 55 omega   46.00   94.00   1.0000    9.9500
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -25.0000 -172.8416 48
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0118156000
_diffrn_orient_matrix_UB_12      -0.1629024000
_diffrn_orient_matrix_UB_13      -0.0475638000
_diffrn_orient_matrix_UB_21      -0.0824485000
_diffrn_orient_matrix_UB_22      0.0545898000
_diffrn_orient_matrix_UB_23      -0.0672325000
_diffrn_orient_matrix_UB_31      0.0723366000
_diffrn_orient_matrix_UB_32      0.0892383000
_diffrn_orient_matrix_UB_33      -0.0457516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3321
_reflns_number_total             3651
_reflns_odcompleteness_completeness 94.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+0.4654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0933
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Si7 Si 0.75089(2) 0.00724(4) 0.95464(2) 0.02685(11) Uani 1 1 d . . .
F5 F 0.53375(6) -0.33225(10) 1.01492(5) 0.03536(19) Uani 1 1 d . . .
F3 F 0.62712(6) -0.49750(9) 1.09499(4) 0.03173(19) Uani 1 1 d . . .
F4 F 0.64922(6) -0.46231(10) 0.97083(4) 0.03515(19) Uani 1 1 d . . .
O6 O 0.68040(6) -0.13140(11) 0.99123(5) 0.02630(19) Uani 1 1 d . . .
C11 C 0.65449(8) -0.14291(15) 1.13300(7) 0.0238(2) Uani 1 1 d . . .
C19 C 0.96127(9) -0.28254(17) 1.15883(7) 0.0279(3) Uani 1 1 d . . .
C18 C 0.85955(8) -0.23509(15) 1.14141(7) 0.0245(2) Uani 1 1 d . . .
H18 H 0.8393 -0.1533 1.1749 0.029 Uiso 1 1 calc R . .
C1 C 0.69178(8) -0.23250(14) 1.06251(7) 0.0227(2) Uani 1 1 d . . .
C17 C 0.79354(9) -0.29688(15) 1.08279(7) 0.0236(2) Uani 1 1 d . . .
H17 H 0.8111 -0.3860 1.0520 0.028 Uiso 1 1 calc R . .
C2 C 0.62458(9) -0.38220(15) 1.03563(7) 0.0267(3) Uani 1 1 d . . .
C16 C 0.66356(9) -0.21749(16) 1.21027(7) 0.0270(3) Uani 1 1 d . . .
H16 H 0.6952 -0.3198 1.2198 0.032 Uiso 1 1 calc R . .
C9 C 0.66414(10) 0.11333(19) 0.87487(9) 0.0395(3) Uani 1 1 d . . .
H9A H 0.6397 0.0338 0.8331 0.059 Uiso 1 1 calc R . .
H9B H 0.6957 0.2032 0.8512 0.059 Uiso 1 1 calc R . .
H9C H 0.6122 0.1579 0.8991 0.059 Uiso 1 1 calc R . .
C20 C 1.01811(10) -0.21046(19) 1.22662(8) 0.0349(3) Uani 1 1 d . . .
H20 H 0.9913 -0.1327 1.2582 0.042 Uiso 1 1 calc R . .
C13 C 0.57049(10) 0.08850(19) 1.18349(10) 0.0403(3) Uani 1 1 d . . .
H13 H 0.5401 0.1920 1.1746 0.048 Uiso 1 1 calc R . .
C21 C 1.11438(10) -0.2533(2) 1.24757(10) 0.0461(4) Uani 1 1 d . . .
H21 H 1.1515 -0.2042 1.2929 0.055 Uiso 1 1 calc R . .
C14 C 0.57894(10) 0.01388(19) 1.25956(10) 0.0393(3) Uani 1 1 d . . .
H14 H 0.5536 0.0661 1.3015 0.047 Uiso 1 1 calc R . .
C15 C 0.62555(9) -0.13955(19) 1.27301(8) 0.0337(3) Uani 1 1 d . . .
H15 H 0.6314 -0.1903 1.3241 0.040 Uiso 1 1 calc R . .
C24 C 1.00372(11) -0.3967(2) 1.11122(9) 0.0402(3) Uani 1 1 d . . .
H24 H 0.9674 -0.4447 1.0652 0.048 Uiso 1 1 calc R . .
C10 C 0.80609(11) 0.16052(18) 1.03322(9) 0.0383(3) Uani 1 1 d . . .
H10A H 0.7567 0.2160 1.0566 0.058 Uiso 1 1 calc R . .
H10B H 0.8420 0.2423 1.0082 0.058 Uiso 1 1 calc R . .
H10C H 0.8481 0.1023 1.0754 0.058 Uiso 1 1 calc R . .
C8 C 0.84746(11) -0.0985(2) 0.91004(9) 0.0395(3) Uani 1 1 d . . .
H8A H 0.8915 -0.1507 0.9528 0.059 Uiso 1 1 calc R . .
H8B H 0.8809 -0.0170 0.8825 0.059 Uiso 1 1 calc R . .
H8C H 0.8200 -0.1824 0.8717 0.059 Uiso 1 1 calc R . .
C12 C 0.60714(9) 0.01010(16) 1.11993(9) 0.0313(3) Uani 1 1 d . . .
H12 H 0.5999 0.0603 1.0686 0.038 Uiso 1 1 calc R . .
C22 C 1.15462(11) -0.3691(2) 1.20080(12) 0.0513(5) Uani 1 1 d . . .
H22 H 1.2185 -0.4001 1.2153 0.062 Uiso 1 1 calc R . .
C23 C 1.09947(12) -0.4383(2) 1.13245(11) 0.0517(4) Uani 1 1 d . . .
H23 H 1.1271 -0.5138 1.1003 0.062 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
Si7 O6 1.6655(9) . ?
Si7 C9 1.8556(13) . ?
Si7 C10 1.8617(15) . ?
Si7 C8 1.8562(15) . ?
F5 C2 1.3358(16) . ?
F3 C2 1.3415(14) . ?
F4 C2 1.3423(15) . ?
O6 C1 1.4170(13) . ?
C11 C1 1.5329(16) . ?
C11 C16 1.3983(17) . ?
C11 C12 1.3898(18) . ?
C19 C18 1.4705(16) . ?
C19 C20 1.395(2) . ?
C19 C24 1.4005(19) . ?
C18 H18 0.9300 . ?
C18 C17 1.3286(17) . ?
C1 C17 1.5137(16) . ?
C1 C2 1.5442(16) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.3910(18) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C21 1.3924(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(2) . ?
C13 C12 1.394(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.383(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C12 H12 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.382(3) . ?
C23 H23 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
O6 Si7 C9 101.24(5) . . ?
O6 Si7 C10 112.80(6) . . ?
O6 Si7 C8 111.52(6) . . ?
C9 Si7 C10 110.78(7) . . ?
C9 Si7 C8 111.54(7) . . ?
C8 Si7 C10 108.84(7) . . ?
C1 O6 Si7 133.28(7) . . ?
C16 C11 C1 120.56(11) . . ?
C12 C11 C1 120.34(11) . . ?
C12 C11 C16 119.04(12) . . ?
C20 C19 C18 118.10(12) . . ?
C20 C19 C24 118.48(13) . . ?
C24 C19 C18 123.42(13) . . ?
C19 C18 H18 116.6 . . ?
C17 C18 C19 126.77(11) . . ?
C17 C18 H18 116.6 . . ?
O6 C1 C11 111.38(10) . . ?
O6 C1 C17 110.69(9) . . ?
O6 C1 C2 102.45(9) . . ?
C11 C1 C2 107.90(9) . . ?
C17 C1 C11 114.83(9) . . ?
C17 C1 C2 108.79(10) . . ?
C18 C17 C1 124.62(11) . . ?
C18 C17 H17 117.7 . . ?
C1 C17 H17 117.7 . . ?
F5 C2 F3 107.63(10) . . ?
F5 C2 F4 107.39(10) . . ?
F5 C2 C1 111.49(10) . . ?
F3 C2 F4 106.39(10) . . ?
F3 C2 C1 111.93(9) . . ?
F4 C2 C1 111.73(10) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.38(13) . . ?
C15 C16 H16 119.8 . . ?
Si7 C9 H9A 109.5 . . ?
Si7 C9 H9B 109.5 . . ?
Si7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.91(15) . . ?
C21 C20 H20 119.5 . . ?
C14 C13 H13 119.7 . . ?
C14 C13 C12 120.61(14) . . ?
C12 C13 H13 119.7 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.81(16) . . ?
C22 C21 H21 120.1 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.58(12) . . ?
C15 C14 H14 120.2 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.19(13) . . ?
C14 C15 H15 119.9 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.19(16) . . ?
C23 C24 H24 119.9 . . ?
Si7 C10 H10A 109.5 . . ?
Si7 C10 H10B 109.5 . . ?
Si7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si7 C8 H8A 109.5 . . ?
Si7 C8 H8B 109.5 . . ?
Si7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C12 C13 120.19(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.71(14) . . ?
C23 C22 H22 120.1 . . ?
C24 C23 H23 119.6 . . ?
C22 C23 C24 120.88(16) . . ?
C22 C23 H23 119.6 . . ?

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
Si7 O6 C1 C11 91.62(12) . . . . ?
Si7 O6 C1 C17 -37.43(14) . . . . ?
Si7 O6 C1 C2 -153.27(9) . . . . ?
O6 C1 C17 C18 102.81(13) . . . . ?
O6 C1 C2 F5 -61.22(12) . . . . ?
O6 C1 C2 F3 178.15(10) . . . . ?
O6 C1 C2 F4 58.95(12) . . . . ?
C11 C1 C17 C18 -24.35(16) . . . . ?
C11 C1 C2 F5 56.40(12) . . . . ?
C11 C1 C2 F3 -64.23(13) . . . . ?
C11 C1 C2 F4 176.57(9) . . . . ?
C11 C16 C15 C14 -0.55(19) . . . . ?
C19 C18 C17 C1 -174.13(11) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
C19 C24 C23 C22 0.3(2) . . . . ?
C18 C19 C20 C21 178.42(12) . . . . ?
C18 C19 C24 C23 -178.50(13) . . . . ?
C1 C11 C16 C15 -176.90(11) . . . . ?
C1 C11 C12 C13 177.84(11) . . . . ?
C17 C1 C2 F5 -178.44(9) . . . . ?
C17 C1 C2 F3 60.93(13) . . . . ?
C17 C1 C2 F4 -58.27(12) . . . . ?
C2 C1 C17 C18 -145.35(12) . . . . ?
C16 C11 C1 O6 -176.66(10) . . . . ?
C16 C11 C1 C17 -49.84(15) . . . . ?
C16 C11 C1 C2 71.65(13) . . . . ?
C16 C11 C12 C13 0.83(18) . . . . ?
C9 Si7 O6 C1 -165.70(11) . . . . ?
C20 C19 C18 C17 -176.04(12) . . . . ?
C20 C19 C24 C23 1.1(2) . . . . ?
C20 C21 C22 C23 1.6(2) . . . . ?
C13 C14 C15 C16 0.05(19) . . . . ?
C21 C22 C23 C24 -1.7(2) . . . . ?
C14 C13 C12 C11 -1.3(2) . . . . ?
C24 C19 C18 C17 3.6(2) . . . . ?
C24 C19 C20 C21 -1.2(2) . . . . ?
C10 Si7 O6 C1 -47.27(12) . . . . ?
C8 Si7 O6 C1 75.57(12) . . . . ?
C12 C11 C1 O6 6.38(15) . . . . ?
C12 C11 C1 C17 133.19(11) . . . . ?
C12 C11 C1 C2 -105.32(12) . . . . ?
C12 C11 C16 C15 0.10(18) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?

