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

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

data_17056
_database_code_depnum_ccdc_archive 'CCDC 1859674'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 F O2'
_chemical_formula_sum            'C11 H11 F O2'
_chemical_formula_weight         194.20

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.560(5)
_cell_length_b                   7.747(7)
_cell_length_c                   22.119(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.199(16)
_cell_angle_gamma                90.00
_cell_volume                     952.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    850
_cell_measurement_theta_min      2.786
_cell_measurement_theta_max      28.200

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.060
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   
;
absoprtion correction based on 1868 reflections(SADABS);Rint 0.1053 before
correction and 0.0613 after.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6281
_diffrn_reflns_av_R_equivalents  0.1163
_diffrn_reflns_av_sigmaI/netI    0.0972
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1872
_reflns_number_gt                1137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0872P)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         1872
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.1789
_refine_ls_wR_factor_gt          0.1612
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4643(3) 0.6056(2) 0.09462(7) 0.0400(5) Uani 1 1 d . . .
O1 O 0.7025(4) 0.6644(3) 0.01645(8) 0.0423(6) Uani 1 1 d . . .
O2 O 0.7296(4) 0.9150(3) -0.03294(9) 0.0560(7) Uani 1 1 d . . .
C1 C 0.7058(5) 0.6058(4) 0.07732(12) 0.0336(7) Uani 1 1 d . . .
C2 C 0.8402(5) 0.7448(4) 0.11349(12) 0.0311(7) Uani 1 1 d . . .
H2 H 1.0162 0.7240 0.1086 0.037 Uiso 1 1 calc R . .
C3 C 0.7750(6) 0.9070(4) 0.07754(12) 0.0408(8) Uani 1 1 d . . .
H3A H 0.6273 0.9614 0.0930 0.049 Uiso 1 1 calc R . .
H3B H 0.9078 0.9921 0.0792 0.049 Uiso 1 1 calc R . .
C4 C 0.7351(5) 0.8399(5) 0.01444(13) 0.0421(9) Uani 1 1 d . . .
C5 C 0.7931(5) 0.7463(3) 0.18061(12) 0.0262(6) Uani 1 1 d . . .
C6 C 0.5910(5) 0.8237(3) 0.20457(12) 0.0305(7) Uani 1 1 d . . .
H6 H 0.4764 0.8770 0.1782 0.037 Uiso 1 1 calc R . .
C7 C 0.5534(5) 0.8245(4) 0.26620(12) 0.0346(7) Uani 1 1 d . . .
H7 H 0.4153 0.8796 0.2818 0.042 Uiso 1 1 calc R . .
C8 C 0.7170(5) 0.7450(4) 0.30507(12) 0.0336(7) Uani 1 1 d . . .
H8 H 0.6907 0.7443 0.3474 0.040 Uiso 1 1 calc R . .
C9 C 0.9185(5) 0.6667(4) 0.28218(13) 0.0358(8) Uani 1 1 d . . .
H9 H 1.0315 0.6121 0.3087 0.043 Uiso 1 1 calc R . .
C10 C 0.9563(5) 0.6675(4) 0.22043(12) 0.0305(7) Uani 1 1 d . . .
H10 H 1.0957 0.6136 0.2050 0.037 Uiso 1 1 calc R . .
C11 C 0.7986(6) 0.4240(4) 0.08036(13) 0.0443(8) Uani 1 1 d . . .
H11A H 0.8013 0.3845 0.1225 0.067 Uiso 1 1 calc R . .
H11B H 0.9619 0.4200 0.0646 0.067 Uiso 1 1 calc R . .
H11C H 0.6932 0.3486 0.0560 0.067 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0350(9) 0.0542(11) 0.0309(10) -0.0083(8) 0.0057(7) -0.0010(8)
O1 0.0498(13) 0.0596(16) 0.0174(11) -0.0040(10) 0.0038(9) 0.0020(11)
O2 0.0590(15) 0.0887(18) 0.0206(12) 0.0146(12) 0.0092(10) 0.0050(13)
C1 0.0322(15) 0.0505(19) 0.0184(15) -0.0050(13) 0.0077(11) 0.0008(14)
C2 0.0274(15) 0.0431(18) 0.0230(16) 0.0017(13) 0.0056(11) -0.0008(13)
C3 0.0520(19) 0.0478(19) 0.0227(16) 0.0074(14) 0.0074(13) -0.0102(16)
C4 0.0365(17) 0.070(3) 0.0199(17) 0.0071(16) 0.0073(12) 0.0018(16)
C5 0.0301(15) 0.0271(15) 0.0216(14) -0.0022(12) 0.0051(11) -0.0016(12)
C6 0.0345(16) 0.0318(16) 0.0253(16) 0.0036(12) 0.0025(12) 0.0009(13)
C7 0.0386(16) 0.0401(18) 0.0256(16) -0.0022(13) 0.0106(12) -0.0020(14)
C8 0.0466(18) 0.0385(17) 0.0159(15) 0.0001(12) 0.0047(12) -0.0100(15)
C9 0.0480(18) 0.0342(17) 0.0248(16) 0.0032(13) -0.0060(13) 0.0003(14)
C10 0.0331(15) 0.0309(16) 0.0276(16) -0.0032(12) 0.0032(12) 0.0031(13)
C11 0.055(2) 0.048(2) 0.0302(18) -0.0093(15) 0.0052(14) 0.0107(16)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.404(3) . ?
O1 C4 1.372(4) . ?
O1 C1 1.421(3) . ?
O2 C4 1.198(4) . ?
C1 C11 1.501(4) . ?
C1 C2 1.527(4) . ?
C2 C5 1.513(4) . ?
C2 C3 1.527(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.502(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.388(4) . ?
C5 C10 1.392(4) . ?
C6 C7 1.384(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C1 110.4(2) . . ?
F1 C1 O1 105.4(2) . . ?
F1 C1 C11 108.4(2) . . ?
O1 C1 C11 109.9(2) . . ?
F1 C1 C2 108.6(2) . . ?
O1 C1 C2 105.5(2) . . ?
C11 C1 C2 118.3(2) . . ?
C5 C2 C3 117.4(2) . . ?
C5 C2 C1 115.2(2) . . ?
C3 C2 C1 101.5(2) . . ?
C5 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
C4 C3 C2 103.2(3) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
O2 C4 O1 120.5(3) . . ?
O2 C4 C3 130.2(4) . . ?
O1 C4 C3 109.3(3) . . ?
C6 C5 C10 118.0(3) . . ?
C6 C5 C2 122.4(2) . . ?
C10 C5 C2 119.6(2) . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 O1 C1 F1 92.9(3) . . . . ?
C4 O1 C1 C11 -150.5(2) . . . . ?
C4 O1 C1 C2 -21.9(3) . . . . ?
F1 C1 C2 C5 46.6(3) . . . . ?
O1 C1 C2 C5 159.1(2) . . . . ?
C11 C1 C2 C5 -77.5(3) . . . . ?
F1 C1 C2 C3 -81.4(2) . . . . ?
O1 C1 C2 C3 31.1(3) . . . . ?
C11 C1 C2 C3 154.5(3) . . . . ?
C5 C2 C3 C4 -155.2(2) . . . . ?
C1 C2 C3 C4 -28.6(3) . . . . ?
C1 O1 C4 O2 -177.4(3) . . . . ?
C1 O1 C4 C3 2.7(3) . . . . ?
C2 C3 C4 O2 -162.5(3) . . . . ?
C2 C3 C4 O1 17.4(3) . . . . ?
C3 C2 C5 C6 38.2(4) . . . . ?
C1 C2 C5 C6 -81.3(3) . . . . ?
C3 C2 C5 C10 -141.9(3) . . . . ?
C1 C2 C5 C10 98.6(3) . . . . ?
C10 C5 C6 C7 0.7(4) . . . . ?
C2 C5 C6 C7 -179.4(3) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C5 -0.1(4) . . . . ?
C6 C5 C10 C9 -0.1(4) . . . . ?
C2 C5 C10 C9 180.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_17085
_database_code_depnum_ccdc_archive 'CCDC 1859676'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21

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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   10.1019(17)
_cell_length_b                   9.4796(16)
_cell_length_c                   9.9375(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     951.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    858
_cell_measurement_theta_min      2.847
_cell_measurement_theta_max      21.082

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
;
absoprtion correction based on 3652 reflections(SADABS);Rint 0.1393 before
correction and 0.0523 after.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6947
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         26.00
_reflns_number_total             994
_reflns_number_gt                919
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0526P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         994
_refine_ls_number_parameters     128
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.48039(18) 0.82725(19) 0.18326(19) 0.0290(5) Uani 1 1 d . . .
O2 O 0.38463(17) 0.91045(18) -0.1052(2) 0.0281(4) Uani 1 1 d . . .
O3 O 0.59684(18) 0.95361(17) -0.1561(2) 0.0290(5) Uani 1 1 d . . .
H3 H 0.5668 1.0326 -0.1793 0.043 Uiso 1 1 calc R . .
C1 C 0.4189(2) 0.7221(2) 0.1511(3) 0.0213(5) Uani 1 1 d . . .
C2 C 0.4470(2) 0.6491(2) 0.0173(3) 0.0212(5) Uani 1 1 d . . .
H2 H 0.3623 0.6460 -0.0347 0.025 Uiso 1 1 calc R . .
C3 C 0.5476(3) 0.7302(3) -0.0664(3) 0.0232(6) Uani 1 1 d . . .
H3A H 0.6299 0.7416 -0.0134 0.028 Uiso 1 1 calc R . .
H3B H 0.5693 0.6746 -0.1477 0.028 Uiso 1 1 calc R . .
C4 C 0.4985(2) 0.8737(3) -0.1086(3) 0.0223(5) Uani 1 1 d . . .
C5 C 0.4904(2) 0.4968(3) 0.0430(3) 0.0208(5) Uani 1 1 d . . .
C6 C 0.4154(2) 0.3851(3) -0.0066(3) 0.0244(6) Uani 1 1 d . . .
H6 H 0.3363 0.4038 -0.0551 0.029 Uiso 1 1 calc R . .
C7 C 0.4554(3) 0.2464(3) 0.0145(3) 0.0272(6) Uani 1 1 d . . .
H7 H 0.4044 0.1708 -0.0209 0.033 Uiso 1 1 calc R . .
C8 C 0.5686(3) 0.2188(3) 0.0864(3) 0.0285(7) Uani 1 1 d . . .
H8 H 0.5955 0.1241 0.1013 0.034 Uiso 1 1 calc R . .
C9 C 0.6439(3) 0.3294(3) 0.1373(3) 0.0268(6) Uani 1 1 d . . .
H9 H 0.7219 0.3104 0.1874 0.032 Uiso 1 1 calc R . .
C10 C 0.6046(2) 0.4672(3) 0.1148(3) 0.0246(6) Uani 1 1 d . . .
H10 H 0.6567 0.5425 0.1490 0.029 Uiso 1 1 calc R . .
C11 C 0.3139(3) 0.6598(3) 0.2386(3) 0.0285(6) Uani 1 1 d . . .
H11A H 0.2985 0.7217 0.3160 0.043 Uiso 1 1 calc R . .
H11B H 0.3426 0.5668 0.2702 0.043 Uiso 1 1 calc R . .
H11C H 0.2318 0.6500 0.1869 0.043 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0339(10) 0.0246(9) 0.0286(11) -0.0066(9) 0.0003(8) -0.0029(8)
O2 0.0266(10) 0.0237(9) 0.0341(11) 0.0001(9) 0.0001(8) 0.0043(7)
O3 0.0318(11) 0.0212(9) 0.0339(11) 0.0051(8) 0.0023(8) -0.0022(7)
C1 0.0213(12) 0.0187(12) 0.0240(14) -0.0006(10) -0.0050(11) 0.0056(10)
C2 0.0203(12) 0.0211(13) 0.0221(14) -0.0010(10) -0.0022(10) 0.0006(10)
C3 0.0249(13) 0.0216(13) 0.0230(14) -0.0009(11) 0.0016(11) 0.0028(10)
C4 0.0285(13) 0.0198(12) 0.0187(12) -0.0043(10) -0.0007(11) -0.0029(10)
C5 0.0231(12) 0.0198(12) 0.0196(11) 0.0008(10) 0.0050(10) -0.0007(10)
C6 0.0218(12) 0.0248(13) 0.0265(14) -0.0019(11) 0.0012(10) -0.0012(10)
C7 0.0342(15) 0.0215(13) 0.0258(16) -0.0037(11) 0.0070(12) -0.0049(12)
C8 0.0364(16) 0.0219(15) 0.0274(16) 0.0023(11) 0.0081(12) 0.0055(12)
C9 0.0268(13) 0.0305(13) 0.0233(14) 0.0031(11) 0.0014(12) 0.0070(11)
C10 0.0271(13) 0.0248(13) 0.0217(13) -0.0010(11) -0.0003(11) -0.0014(10)
C11 0.0278(14) 0.0306(14) 0.0270(14) -0.0016(12) 0.0032(11) 0.0026(10)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.218(3) . ?
O2 C4 1.203(3) . ?
O3 C4 1.335(3) . ?
O3 H3 0.8400 . ?
C1 C11 1.493(4) . ?
C1 C2 1.525(4) . ?
C2 C3 1.521(4) . ?
C2 C5 1.530(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C10 1.386(4) . ?
C5 C6 1.392(4) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 H3 109.5 . . ?
O1 C1 C11 122.2(3) . . ?
O1 C1 C2 120.3(2) . . ?
C11 C1 C2 117.4(2) . . ?
C3 C2 C1 111.82(19) . . ?
C3 C2 C5 112.1(2) . . ?
C1 C2 C5 109.6(2) . . ?
C3 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C5 C2 H2 107.7 . . ?
C4 C3 C2 112.9(2) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O2 C4 O3 123.9(3) . . ?
O2 C4 C3 124.6(2) . . ?
O3 C4 C3 111.5(2) . . ?
C10 C5 C6 118.8(2) . . ?
C10 C5 C2 121.0(2) . . ?
C6 C5 C2 120.2(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 C1 C2 C3 -4.5(3) . . . . ?
C11 C1 C2 C3 175.3(2) . . . . ?
O1 C1 C2 C5 120.5(2) . . . . ?
C11 C1 C2 C5 -59.7(3) . . . . ?
C1 C2 C3 C4 -64.2(3) . . . . ?
C5 C2 C3 C4 172.2(2) . . . . ?
C2 C3 C4 O2 -16.0(4) . . . . ?
C2 C3 C4 O3 166.6(2) . . . . ?
C3 C2 C5 C10 62.5(3) . . . . ?
C1 C2 C5 C10 -62.3(3) . . . . ?
C3 C2 C5 C6 -117.1(3) . . . . ?
C1 C2 C5 C6 118.1(3) . . . . ?
C10 C5 C6 C7 -0.7(4) . . . . ?
C2 C5 C6 C7 178.9(2) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C5 0.6(4) . . . . ?
C6 C5 C10 C9 -0.1(4) . . . . ?
C2 C5 C10 C9 -179.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.84 1.96 2.734(3) 151.8 2_674

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_17068
_database_code_depnum_ccdc_archive 'CCDC 1859675'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 F O2'
_chemical_formula_sum            'C11 H11 F O2'
_chemical_formula_weight         194.20

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

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

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

_cell_length_a                   5.605(2)
_cell_length_b                   7.129(3)
_cell_length_c                   24.013(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     959.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1016
_cell_measurement_theta_min      3.324
_cell_measurement_theta_max      23.326

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   
; 
absorption correction based on 3977 refections(SADABS);Rint 0.0699 before 
correction and 0.0478 after. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7366
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.98
_reflns_number_total             1877
_reflns_number_gt                1650
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.0296P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ,syn
_refine_ls_number_reflns         1877
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3595(3) 0.1410(2) 0.75622(5) 0.0471(4) Uani 1 1 d . . .
O1 O 0.0031(3) 0.1855(2) 0.84806(6) 0.0330(4) Uani 1 1 d . . .
O2 O -0.0753(4) -0.1152(2) 0.86453(7) 0.0487(5) Uani 1 1 d . . .
C1 C 0.2097(4) 0.3058(3) 0.83629(9) 0.0287(5) Uani 1 1 d . . .
C2 C 0.3947(4) 0.1659(3) 0.81376(9) 0.0328(5) Uani 1 1 d . . .
H2 H 0.5615 0.2065 0.8224 0.039 Uiso 1 1 calc R . .
C3 C 0.3313(5) -0.0143(3) 0.84307(11) 0.0401(6) Uani 1 1 d . . .
H3A H 0.3666 -0.1243 0.8193 0.048 Uiso 1 1 calc R . .
H3B H 0.4202 -0.0266 0.8785 0.048 Uiso 1 1 calc R . .
C4 C 0.0692(4) 0.0028(3) 0.85348(9) 0.0351(6) Uani 1 1 d . . .
C5 C 0.2985(4) 0.3936(3) 0.89011(9) 0.0253(5) Uani 1 1 d . . .
C6 C 0.5046(4) 0.5026(3) 0.88944(9) 0.0309(5) Uani 1 1 d . . .
H6 H 0.5886 0.5196 0.8555 0.037 Uiso 1 1 calc R . .
C7 C 0.5887(5) 0.5865(3) 0.93746(9) 0.0349(6) Uani 1 1 d . . .
H7 H 0.7302 0.6598 0.9362 0.042 Uiso 1 1 calc R . .
C8 C 0.4690(5) 0.5644(3) 0.98692(10) 0.0385(6) Uani 1 1 d . . .
H8 H 0.5265 0.6226 1.0199 0.046 Uiso 1 1 calc R . .
C9 C 0.2633(5) 0.4563(3) 0.98828(10) 0.0393(6) Uani 1 1 d . . .
H9 H 0.1803 0.4402 1.0224 0.047 Uiso 1 1 calc R . .
C10 C 0.1781(4) 0.3721(3) 0.94076(9) 0.0318(5) Uani 1 1 d . . .
H10 H 0.0366 0.2990 0.9423 0.038 Uiso 1 1 calc R . .
C11 C 0.1278(5) 0.4508(3) 0.79475(9) 0.0378(6) Uani 1 1 d . . .
H11A H 0.0610 0.3878 0.7620 0.057 Uiso 1 1 calc R . .
H11B H 0.2638 0.5284 0.7835 0.057 Uiso 1 1 calc R . .
H11C H 0.0054 0.5303 0.8118 0.057 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0406(9) 0.0651(11) 0.0357(8) -0.0159(7) 0.0028(6) -0.0020(8)
O1 0.0237(8) 0.0328(8) 0.0425(9) 0.0001(7) -0.0023(7) -0.0019(7)
O2 0.0579(13) 0.0376(10) 0.0505(10) 0.0037(8) -0.0011(9) -0.0184(9)
C1 0.0245(11) 0.0292(12) 0.0325(12) 0.0028(9) -0.0004(9) -0.0033(10)
C2 0.0244(11) 0.0411(14) 0.0331(12) -0.0110(10) -0.0027(9) -0.0013(11)
C3 0.0403(14) 0.0299(12) 0.0502(15) -0.0070(11) -0.0095(11) 0.0061(12)
C4 0.0468(15) 0.0283(12) 0.0303(12) -0.0027(10) -0.0087(10) -0.0051(13)
C5 0.0257(11) 0.0188(10) 0.0314(11) 0.0014(9) 0.0017(9) 0.0050(10)
C6 0.0323(12) 0.0296(11) 0.0310(11) 0.0000(10) 0.0025(9) -0.0005(11)
C7 0.0344(14) 0.0259(12) 0.0443(14) -0.0036(10) -0.0037(11) 0.0000(11)
C8 0.0506(17) 0.0306(12) 0.0343(13) -0.0062(10) -0.0068(12) 0.0059(12)
C9 0.0483(17) 0.0416(14) 0.0281(12) 0.0029(10) 0.0094(11) 0.0102(12)
C10 0.0314(13) 0.0279(12) 0.0363(13) 0.0023(10) 0.0047(10) 0.0005(12)
C11 0.0366(15) 0.0398(14) 0.0369(13) 0.0045(11) -0.0052(11) -0.0020(11)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.407(2) . ?
O1 C4 1.360(3) . ?
O1 C1 1.468(3) . ?
O2 C4 1.197(3) . ?
C1 C11 1.508(3) . ?
C1 C5 1.520(3) . ?
C1 C2 1.537(3) . ?
C2 C3 1.508(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.495(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.392(3) . ?
C5 C10 1.399(3) . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C1 111.28(18) . . ?
O1 C1 C11 106.71(18) . . ?
O1 C1 C5 109.58(17) . . ?
C11 C1 C5 112.34(18) . . ?
O1 C1 C2 102.77(17) . . ?
C11 C1 C2 114.65(19) . . ?
C5 C1 C2 110.22(17) . . ?
F1 C2 C3 108.53(18) . . ?
F1 C2 C1 109.45(18) . . ?
C3 C2 C1 103.26(18) . . ?
F1 C2 H2 111.7 . . ?
C3 C2 H2 111.7 . . ?
C1 C2 H2 111.7 . . ?
C4 C3 C2 103.9(2) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
O2 C4 O1 120.7(2) . . ?
O2 C4 C3 130.1(2) . . ?
O1 C4 C3 109.2(2) . . ?
C6 C5 C10 118.1(2) . . ?
C6 C5 C1 119.46(18) . . ?
C10 C5 C1 122.4(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 O1 C1 C11 141.46(18) . . . . ?
C4 O1 C1 C5 -96.7(2) . . . . ?
C4 O1 C1 C2 20.5(2) . . . . ?
O1 C1 C2 F1 85.7(2) . . . . ?
C11 C1 C2 F1 -29.7(3) . . . . ?
C5 C1 C2 F1 -157.58(17) . . . . ?
O1 C1 C2 C3 -29.7(2) . . . . ?
C11 C1 C2 C3 -145.09(19) . . . . ?
C5 C1 C2 C3 87.0(2) . . . . ?
F1 C2 C3 C4 -87.5(2) . . . . ?
C1 C2 C3 C4 28.6(2) . . . . ?
C1 O1 C4 O2 178.1(2) . . . . ?
C1 O1 C4 C3 -2.4(2) . . . . ?
C2 C3 C4 O2 162.2(2) . . . . ?
C2 C3 C4 O1 -17.1(2) . . . . ?
O1 C1 C5 C6 175.35(17) . . . . ?
C11 C1 C5 C6 -66.2(3) . . . . ?
C2 C1 C5 C6 63.0(2) . . . . ?
O1 C1 C5 C10 -5.9(3) . . . . ?
C11 C1 C5 C10 112.5(2) . . . . ?
C2 C1 C5 C10 -118.3(2) . . . . ?
C10 C5 C6 C7 0.4(3) . . . . ?
C1 C5 C6 C7 179.2(2) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C6 C5 C10 C9 -0.3(3) . . . . ?
C1 C5 C10 C9 -179.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.042


