# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FR1170

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 F O'
_chemical_formula_sum            'C16 H19 F O'
_chemical_formula_weight         246.31
_chemical_absolute_configuration ad


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'
O O 0.0492 0.0322 '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 1'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   8.9713(3)
_cell_length_b                   7.80672(18)
_cell_length_c                   9.9760(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.826(4)
_cell_angle_gamma                90.00
_cell_volume                     648.60(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4585
_cell_measurement_theta_min      4.7450
_cell_measurement_theta_max      72.5490

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3978
_exptl_crystal_size_mid          0.1003
_exptl_crystal_size_min          0.0534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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_detector_area_resol_mean 10.4679
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            5983
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.78
_diffrn_reflns_theta_max         72.55
_reflns_number_total             2477
_reflns_number_gt                2420
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  ShelX_acta

_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)+(0.0500P)²+0.0430P] 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   -0.02(14)
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.065
_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 -0.09922(11) 0.37031(14) 0.84107(12) 0.0600(3) Uani 1 1 d . . .
O14 O -0.08326(12) 0.32589(15) 0.51915(11) 0.0477(3) Uani 1 1 d . . .
C2 C 0.09231(18) 0.55869(19) 0.81051(17) 0.0438(3) Uani 1 1 d . . .
H2A H 0.0616 0.6439 0.8691 0.053 Uiso 1 1 calc R . .
H2B H 0.0257 0.5791 0.7076 0.053 Uiso 1 1 calc R . .
C1 C 0.06191(17) 0.38161(18) 0.85247(15) 0.0376(3) Uani 1 1 d . . .
H1 H 0.1327 0.3626 0.9557 0.045 Uiso 1 1 calc R . .
C3 C 0.26935(18) 0.58054(17) 0.83426(15) 0.0380(3) Uani 1 1 d . . .
H3 H 0.2806 0.6910 0.7881 0.046 Uiso 1 1 calc R . .
C17 C 0.09440(16) 0.06241(19) 0.83137(15) 0.0377(3) Uani 1 1 d . . .
H17A H 0.1615 -0.0204 0.8037 0.045 Uiso 1 1 calc R . .
H17B H 0.1362 0.0720 0.9379 0.045 Uiso 1 1 calc R . .
C16 C -0.08222(18) 0.0048(2) 0.77329(16) 0.0422(3) Uani 1 1 d . . .
H16A H -0.0908 -0.1212 0.7787 0.051 Uiso 1 1 calc R . .
H16B H -0.1419 0.0591 0.8279 0.051 Uiso 1 1 calc R . .
C4 C 0.3744(2) 0.5927(2) 0.99602(16) 0.0514(4) Uani 1 1 d . . .
H4A H 0.3683 0.4846 1.0437 0.077 Uiso 1 1 calc R . .
H4B H 0.3357 0.6864 1.0399 0.077 Uiso 1 1 calc R . .
H4C H 0.4860 0.6146 1.0074 0.077 Uiso 1 1 calc R . .
C13 C -0.05205(14) 0.22540(16) 0.61708(12) 0.0295(3) Uani 1 1 d . . .
C7 C 0.5473(2) 0.6355(2) 0.74883(17) 0.0471(3) Uani 1 1 d . . .
H7A H 0.4720 0.7262 0.6981 0.071 Uiso 1 1 calc R . .
H7B H 0.6349 0.6302 0.7126 0.071 Uiso 1 1 calc R . .
H7C H 0.5915 0.6603 0.8526 0.071 Uiso 1 1 calc R . .
C15 C -0.14482(15) 0.06552(18) 0.61765(14) 0.0359(3) Uani 1 1 d . . .
H15A H -0.1267 -0.0227 0.5540 0.043 Uiso 1 1 calc R . .
H15B H -0.2612 0.0903 0.5838 0.043 Uiso 1 1 calc R . .
C10 C 0.29979(15) 0.15372(17) 0.65901(14) 0.0336(3) Uani 1 1 d . . .
H10 H 0.2442 0.0476 0.6351 0.040 Uiso 1 1 calc R . .
C6 C 0.46039(15) 0.46537(16) 0.72307(13) 0.0337(3) Uani 1 1 d . . .
C8 C 0.51201(16) 0.33714(18) 0.65508(14) 0.0365(3) Uani 1 1 d . . .
H8 H 0.6030 0.3559 0.6300 0.044 Uiso 1 1 calc R . .
C5 C 0.32602(15) 0.43806(15) 0.76136(12) 0.0297(3) Uani 1 1 d . . .
C11 C 0.24623(15) 0.27963(14) 0.73006(12) 0.0279(2) Uani 1 1 d . . .
C12 C 0.09531(15) 0.23948(16) 0.76158(12) 0.0292(3) Uani 1 1 d . . .
C9 C 0.43220(16) 0.18129(18) 0.62304(15) 0.0379(3) Uani 1 1 d . . .
H9 H 0.4686 0.0938 0.5765 0.045 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 0.0425(5) 0.0661(6) 0.0805(7) -0.0279(5) 0.0332(5) -0.0007(4)
O14 0.0403(5) 0.0526(6) 0.0394(5) 0.0169(5) 0.0023(4) 0.0028(5)
C2 0.0473(8) 0.0355(7) 0.0469(8) -0.0092(6) 0.0155(6) 0.0119(6)
C1 0.0349(7) 0.0426(7) 0.0375(7) -0.0088(6) 0.0160(6) 0.0029(6)
C3 0.0486(8) 0.0273(6) 0.0371(7) -0.0063(5) 0.0146(6) 0.0002(6)
C17 0.0379(7) 0.0389(7) 0.0351(7) 0.0091(6) 0.0121(5) 0.0068(6)
C16 0.0439(8) 0.0400(7) 0.0485(8) 0.0070(6) 0.0239(6) 0.0017(6)
C4 0.0594(9) 0.0544(9) 0.0382(7) -0.0195(7) 0.0155(7) -0.0144(7)
C13 0.0274(6) 0.0325(6) 0.0288(6) -0.0013(5) 0.0106(5) 0.0045(5)
C7 0.0511(8) 0.0419(8) 0.0452(8) -0.0021(7) 0.0144(7) -0.0126(7)
C15 0.0311(6) 0.0369(7) 0.0408(7) -0.0075(5) 0.0147(5) -0.0022(5)
C10 0.0321(6) 0.0298(6) 0.0360(6) -0.0074(5) 0.0094(5) 0.0000(5)
C6 0.0329(6) 0.0334(6) 0.0278(6) 0.0028(5) 0.0031(5) -0.0013(5)
C8 0.0312(6) 0.0429(8) 0.0349(6) 0.0026(6) 0.0118(5) 0.0011(5)
C5 0.0332(6) 0.0284(6) 0.0215(5) -0.0004(4) 0.0034(4) 0.0033(5)
C11 0.0266(6) 0.0295(6) 0.0236(5) -0.0006(4) 0.0046(4) 0.0035(4)
C12 0.0294(6) 0.0289(6) 0.0265(5) -0.0005(5) 0.0071(5) 0.0043(5)
C9 0.0355(7) 0.0405(7) 0.0381(7) -0.0072(5) 0.0141(5) 0.0049(5)

_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 1.4100(16) . ?
O14 C13 1.2021(15) . ?
C2 C1 1.499(2) . ?
C2 C3 1.526(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 C12 1.5314(17) . ?
C1 H1 1.0000 . ?
C3 C5 1.5164(17) . ?
C3 C4 1.540(2) . ?
C3 H3 1.0000 . ?
C17 C16 1.538(2) . ?
C17 C12 1.5492(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C16 C15 1.517(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C13 C15 1.5014(18) . ?
C13 C12 1.5559(16) . ?
C7 C6 1.5131(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C10 C9 1.3795(18) . ?
C10 C11 1.3974(17) . ?
C10 H10 0.9500 . ?
C6 C8 1.3822(19) . ?
C6 C5 1.4096(18) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C5 C11 1.4048(16) . ?
C11 C12 1.5319(16) . ?
C9 H9 0.9500 . ?

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
C1 C2 C3 110.29(12) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
F1 C1 C2 108.83(11) . . ?
F1 C1 C12 109.11(11) . . ?
C2 C1 C12 114.02(11) . . ?
F1 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C12 C1 H1 108.2 . . ?
C5 C3 C2 111.02(11) . . ?
C5 C3 C4 111.35(12) . . ?
C2 C3 C4 111.46(12) . . ?
C5 C3 H3 107.6 . . ?
C2 C3 H3 107.6 . . ?
C4 C3 H3 107.6 . . ?
C16 C17 C12 105.56(11) . . ?
C16 C17 H17A 110.6 . . ?
C12 C17 H17A 110.6 . . ?
C16 C17 H17B 110.6 . . ?
C12 C17 H17B 110.6 . . ?
H17A C17 H17B 108.8 . . ?
C15 C16 C17 103.40(11) . . ?
C15 C16 H16A 111.1 . . ?
C17 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
C17 C16 H16B 111.1 . . ?
H16A C16 H16B 109.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O14 C13 C15 125.71(11) . . ?
O14 C13 C12 124.60(12) . . ?
C15 C13 C12 109.66(10) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C15 C16 105.58(11) . . ?
C13 C15 H15A 110.6 . . ?
C16 C15 H15A 110.6 . . ?
C13 C15 H15B 110.6 . . ?
C16 C15 H15B 110.6 . . ?
H15A C15 H15B 108.8 . . ?
C9 C10 C11 120.92(12) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C8 C6 C5 119.99(11) . . ?
C8 C6 C7 118.26(12) . . ?
C5 C6 C7 121.71(12) . . ?
C6 C8 C9 120.65(12) . . ?
C6 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C11 C5 C6 119.30(11) . . ?
C11 C5 C3 121.23(11) . . ?
C6 C5 C3 119.47(11) . . ?
C10 C11 C5 119.29(11) . . ?
C10 C11 C12 117.19(10) . . ?
C5 C11 C12 123.42(10) . . ?
C1 C12 C11 110.84(10) . . ?
C1 C12 C17 110.21(10) . . ?
C11 C12 C17 115.31(10) . . ?
C1 C12 C13 108.29(10) . . ?
C11 C12 C13 109.61(9) . . ?
C17 C12 C13 102.05(10) . . ?
C10 C9 C8 119.84(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.027
_database_code_depnum_ccdc_archive 'CCDC 1015663'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FR1221

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 F O2'
_chemical_formula_sum            'C16 H19 F O2'
_chemical_formula_weight         262.31
_chemical_absolute_configuration ad

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   6.10937(8)
_cell_length_b                   10.50654(13)
_cell_length_c                   21.0764(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1352.86(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4243
_cell_measurement_theta_min      4.1350
_cell_measurement_theta_max      72.5560

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2832
_exptl_crystal_size_mid          0.1300
_exptl_crystal_size_min          0.0760
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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_detector_area_resol_mean 10.4679
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6288
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.20
_diffrn_reflns_theta_max         72.70
_reflns_number_total             2622
_reflns_number_gt                2501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  ShelX_acta

_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)+(0.0560P)²+0.0900P] 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   0.10(15)
_refine_ls_number_reflns         2622
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.29956(18) 0.30938(8) 0.68996(4) 0.0456(2) Uani 1 1 d . . .
O4 O 0.64773(17) 0.45765(12) 0.74366(6) 0.0523(3) Uani 1 1 d . . .
O13 O 0.57543(19) 0.51733(13) 0.46695(5) 0.0476(3) Uani 1 1 d . . .
C1 C 0.1837(2) 0.42134(14) 0.67348(6) 0.0340(3) Uani 1 1 d . . .
H1 H 0.0482 0.4256 0.7000 0.041 Uiso 1 1 calc R . .
C2 C 0.3245(2) 0.53934(12) 0.68814(6) 0.0288(3) Uani 1 1 d . . .
C3 C 0.4707(2) 0.50771(12) 0.74587(7) 0.0341(3) Uani 1 1 d . . .
C5 C 0.3601(3) 0.55335(16) 0.80550(7) 0.0470(4) Uani 1 1 d . . .
H5A H 0.4489 0.6202 0.8263 0.056 Uiso 1 1 calc R . .
H5B H 0.3402 0.4820 0.8356 0.056 Uiso 1 1 calc R . .
C6 C 0.1405(3) 0.60625(19) 0.78531(8) 0.0495(4) Uani 1 1 d . . .
H6A H 0.1010 0.6816 0.8111 0.059 Uiso 1 1 calc R . .
H6B H 0.0242 0.5413 0.7898 0.059 Uiso 1 1 calc R . .
C7 C 0.1718(2) 0.64281(14) 0.71568(7) 0.0391(3) Uani 1 1 d . . .
H7A H 0.2398 0.7281 0.7120 0.047 Uiso 1 1 calc R . .
H7B H 0.0298 0.6436 0.6931 0.047 Uiso 1 1 calc R . .
C8 C 0.4622(2) 0.58534(12) 0.63274(6) 0.0303(3) Uani 1 1 d . . .
C9 C 0.6030(2) 0.68922(15) 0.64342(8) 0.0407(3) Uani 1 1 d . . .
H9 H 0.6090 0.7277 0.6842 0.049 Uiso 1 1 calc R . .
C10 C 0.7323(3) 0.73533(15) 0.59487(9) 0.0478(4) Uani 1 1 d . . .
H10 H 0.8251 0.8063 0.6025 0.057 Uiso 1 1 calc R . .
C11 C 0.7291(2) 0.68002(16) 0.53539(9) 0.0456(4) Uani 1 1 d . . .
H11 H 0.8198 0.7119 0.5024 0.055 Uiso 1 1 calc R . .
C12 C 0.5921(2) 0.57780(15) 0.52456(7) 0.0369(3) Uani 1 1 d . . .
C14 C 0.7315(3) 0.5508(2) 0.41941(8) 0.0608(5) Uani 1 1 d . . .
H14A H 0.8796 0.5427 0.4368 0.091 Uiso 1 1 calc R . .
H14B H 0.7067 0.6389 0.4059 0.091 Uiso 1 1 calc R . .
H14C H 0.7154 0.4938 0.3829 0.091 Uiso 1 1 calc R . .
C15 C 0.4538(2) 0.52947(12) 0.57269(6) 0.0296(3) Uani 1 1 d . . .
C16 C 0.3085(2) 0.41715(14) 0.55847(6) 0.0330(3) Uani 1 1 d . . .
H16 H 0.2461 0.4305 0.5151 0.040 Uiso 1 1 calc R . .
C17 C 0.4425(3) 0.29389(14) 0.55646(8) 0.0461(4) Uani 1 1 d . . .
H17A H 0.5476 0.2980 0.5214 0.069 Uiso 1 1 calc R . .
H17B H 0.3441 0.2213 0.5501 0.069 Uiso 1 1 calc R . .
H17C H 0.5215 0.2835 0.5966 0.069 Uiso 1 1 calc R . .
C18 C 0.1167(2) 0.41258(15) 0.60487(7) 0.0357(3) Uani 1 1 d . . .
H18A H 0.0157 0.4837 0.5951 0.043 Uiso 1 1 calc R . .
H18B H 0.0355 0.3321 0.5983 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
F1 0.0666(6) 0.0285(4) 0.0416(4) 0.0073(3) -0.0049(4) -0.0070(4)
O4 0.0281(5) 0.0538(6) 0.0749(8) 0.0178(6) -0.0068(5) 0.0072(5)
O13 0.0440(6) 0.0617(7) 0.0370(5) 0.0143(5) 0.0097(5) 0.0028(6)
C1 0.0294(6) 0.0346(7) 0.0380(7) 0.0007(5) 0.0054(5) -0.0068(6)
C2 0.0235(6) 0.0265(6) 0.0364(6) -0.0001(5) -0.0008(5) 0.0013(5)
C3 0.0286(6) 0.0273(6) 0.0463(7) 0.0058(5) -0.0065(6) -0.0015(5)
C5 0.0589(10) 0.0435(8) 0.0386(7) -0.0033(6) -0.0077(7) -0.0044(8)
C6 0.0479(9) 0.0560(9) 0.0447(8) -0.0106(7) 0.0075(7) 0.0057(8)
C7 0.0319(7) 0.0386(7) 0.0467(8) -0.0022(6) -0.0004(6) 0.0106(6)
C8 0.0239(6) 0.0230(5) 0.0441(7) 0.0041(5) -0.0005(5) 0.0008(5)
C9 0.0320(7) 0.0291(6) 0.0611(9) 0.0004(6) -0.0002(6) -0.0036(6)
C10 0.0314(7) 0.0307(7) 0.0812(12) 0.0125(7) 0.0027(8) -0.0075(6)
C11 0.0299(7) 0.0406(7) 0.0661(10) 0.0239(7) 0.0089(7) 0.0001(7)
C12 0.0278(7) 0.0378(7) 0.0450(7) 0.0164(6) 0.0032(6) 0.0070(6)
C14 0.0424(9) 0.0951(15) 0.0448(8) 0.0259(9) 0.0135(8) 0.0125(10)
C15 0.0235(6) 0.0263(6) 0.0390(7) 0.0090(5) 0.0002(5) 0.0027(5)
C16 0.0339(7) 0.0349(7) 0.0301(6) 0.0037(5) -0.0024(5) -0.0045(6)
C17 0.0546(9) 0.0319(7) 0.0517(8) -0.0028(6) 0.0091(8) 0.0000(7)
C18 0.0278(6) 0.0380(7) 0.0414(7) 0.0010(6) -0.0023(5) -0.0088(6)

_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 1.4161(17) . ?
O4 C3 1.2035(18) . ?
O13 C12 1.374(2) . ?
O13 C14 1.4271(19) . ?
C1 C18 1.5058(19) . ?
C1 C2 1.5404(17) . ?
C1 H1 1.0000 . ?
C2 C8 1.5181(18) . ?
C2 C3 1.5456(18) . ?
C2 C7 1.5457(18) . ?
C3 C5 1.505(2) . ?
C5 C6 1.513(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C15 1.3959(19) . ?
C8 C9 1.408(2) . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 C15 1.4144(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.5069(18) . ?
C16 C18 1.5271(19) . ?
C16 C17 1.533(2) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O13 C14 117.19(15) . . ?
F1 C1 C18 108.71(12) . . ?
F1 C1 C2 109.89(10) . . ?
C18 C1 C2 113.18(12) . . ?
F1 C1 H1 108.3 . . ?
C18 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
C8 C2 C1 114.30(11) . . ?
C8 C2 C3 110.72(11) . . ?
C1 C2 C3 107.91(10) . . ?
C8 C2 C7 113.54(11) . . ?
C1 C2 C7 107.71(11) . . ?
C3 C2 C7 101.79(11) . . ?
O4 C3 C5 125.10(15) . . ?
O4 C3 C2 125.65(15) . . ?
C5 C3 C2 109.23(11) . . ?
C3 C5 C6 106.29(12) . . ?
C3 C5 H5A 110.5 . . ?
C6 C5 H5A 110.5 . . ?
C3 C5 H5B 110.5 . . ?
C6 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C5 C6 C7 104.54(13) . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6B 110.8 . . ?
C7 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C6 C7 C2 105.03(12) . . ?
C6 C7 H7A 110.7 . . ?
C2 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C2 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C15 C8 C9 119.57(13) . . ?
C15 C8 C2 122.89(12) . . ?
C9 C8 C2 117.54(12) . . ?
C10 C9 C8 120.21(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.11(15) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 119.07(14) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
O13 C12 C11 123.42(13) . . ?
O13 C12 C15 115.06(13) . . ?
C11 C12 C15 121.51(15) . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 C12 118.51(13) . . ?
C8 C15 C16 122.10(11) . . ?
C12 C15 C16 119.36(13) . . ?
C15 C16 C18 110.45(11) . . ?
C15 C16 C17 110.65(12) . . ?
C18 C16 C17 113.64(12) . . ?
C15 C16 H16 107.3 . . ?
C18 C16 H16 107.3 . . ?
C17 C16 H16 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 C16 113.85(11) . . ?
C1 C18 H18A 108.8 . . ?
C16 C18 H18A 108.8 . . ?
C1 C18 H18B 108.8 . . ?
C16 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1015664'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FR1194

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 F2 O'
_chemical_formula_sum            'C15 H16 F2 O'
_chemical_formula_weight         250.28
_chemical_absolute_configuration ad


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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   6.83236(18)
_cell_length_b                   7.7016(2)
_cell_length_c                   23.5545(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1239.45(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7913
_cell_measurement_theta_min      3.7010
_cell_measurement_theta_max      72.4410

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2945
_exptl_crystal_size_mid          0.2561
_exptl_crystal_size_min          0.1611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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_detector_area_resol_mean 10.4679
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            11491
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         72.55
_reflns_number_total             2438
_reflns_number_gt                2385
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  ShelX_Acta

_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)+(0.0450P)²+0.2880P] 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   0.01(14)
_refine_ls_number_reflns         2438
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.54304(15) 0.17581(14) 0.52977(4) 0.0442(3) Uani 1 1 d . . .
F2 F 0.83897(16) 0.38969(18) 0.72300(5) 0.0614(3) Uani 1 1 d . . .
O1 O 0.51772(18) -0.18514(16) 0.56357(6) 0.0476(3) Uani 1 1 d . . .
C1 C 0.3710(2) -0.1096(2) 0.57710(7) 0.0325(3) Uani 1 1 d . . .
C2 C 0.1642(3) -0.1736(3) 0.56749(9) 0.0470(4) Uani 1 1 d . . .
H2A H 0.1415 -0.2832 0.5885 0.056 Uiso 1 1 calc R . .
H2B H 0.1409 -0.1948 0.5266 0.056 Uiso 1 1 calc R . .
C3 C 0.0291(2) -0.0317(2) 0.58929(8) 0.0420(4) Uani 1 1 d . . .
H3A H -0.0899 -0.0818 0.6068 0.050 Uiso 1 1 calc R . .
H3B H -0.0103 0.0475 0.5582 0.050 Uiso 1 1 calc R . .
C4 C 0.1537(2) 0.0637(2) 0.63358(6) 0.0320(3) Uani 1 1 d . . .
H4A H 0.1497 0.0022 0.6705 0.038 Uiso 1 1 calc R . .
H4B H 0.1054 0.1838 0.6391 0.038 Uiso 1 1 calc R . .
C5 C 0.3644(2) 0.06492(18) 0.60924(6) 0.0247(3) Uani 1 1 d . . .
C6 C 0.3814(2) 0.2109(2) 0.56534(6) 0.0329(3) Uani 1 1 d . . .
H6 H 0.2597 0.2131 0.5418 0.039 Uiso 1 1 calc R . .
C7 C 0.4092(2) 0.3862(2) 0.59217(8) 0.0383(4) Uani 1 1 d . . .
H7A H 0.2923 0.4137 0.6153 0.046 Uiso 1 1 calc R . .
H7B H 0.4188 0.4746 0.5618 0.046 Uiso 1 1 calc R . .
C8 C 0.5912(2) 0.39863(19) 0.62991(7) 0.0356(3) Uani 1 1 d . . .
H8 H 0.5689 0.4966 0.6570 0.043 Uiso 1 1 calc R . .
C9 C 0.7774(3) 0.4419(3) 0.59598(9) 0.0460(4) Uani 1 1 d . . .
H9A H 0.8873 0.4582 0.6222 0.069 Uiso 1 1 calc R . .
H9B H 0.7566 0.5489 0.5743 0.069 Uiso 1 1 calc R . .
H9C H 0.8070 0.3464 0.5699 0.069 Uiso 1 1 calc R . .
C10 C 0.6175(2) 0.2353(2) 0.66513(6) 0.0300(3) Uani 1 1 d . . .
C11 C 0.7474(2) 0.2371(3) 0.71106(7) 0.0417(4) Uani 1 1 d . . .
C12 C 0.7872(3) 0.0973(3) 0.74462(7) 0.0505(5) Uani 1 1 d . . .
H12 H 0.8778 0.1057 0.7751 0.061 Uiso 1 1 calc R . .
C13 C 0.6926(3) -0.0561(3) 0.73310(7) 0.0490(5) Uani 1 1 d . . .
H13 H 0.7186 -0.1561 0.7555 0.059 Uiso 1 1 calc R . .
C14 C 0.5591(2) -0.0651(2) 0.68877(7) 0.0371(4) Uani 1 1 d . . .
H14 H 0.4931 -0.1713 0.6814 0.045 Uiso 1 1 calc R . .
C15 C 0.52026(19) 0.07976(19) 0.65474(5) 0.0261(3) Uani 1 1 d . . .

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 0.0466(5) 0.0555(6) 0.0304(4) 0.0041(4) 0.0108(4) -0.0102(5)
F2 0.0438(6) 0.0810(8) 0.0594(7) -0.0286(6) -0.0080(5) -0.0144(6)
O1 0.0388(6) 0.0424(7) 0.0616(8) -0.0166(6) 0.0086(6) 0.0038(5)
C1 0.0322(8) 0.0312(7) 0.0340(7) -0.0029(6) 0.0024(6) -0.0009(6)
C2 0.0377(9) 0.0426(9) 0.0606(11) -0.0097(8) -0.0032(8) -0.0104(8)
C3 0.0247(8) 0.0484(10) 0.0529(10) 0.0018(8) -0.0026(7) -0.0059(7)
C4 0.0223(7) 0.0389(8) 0.0349(7) 0.0025(6) 0.0038(6) 0.0020(6)
C5 0.0219(6) 0.0263(6) 0.0261(6) 0.0004(5) 0.0026(5) 0.0006(5)
C6 0.0277(7) 0.0397(8) 0.0313(7) 0.0087(6) -0.0022(6) -0.0018(6)
C7 0.0312(8) 0.0299(7) 0.0539(9) 0.0111(7) -0.0002(7) 0.0050(6)
C8 0.0301(7) 0.0263(7) 0.0503(9) -0.0065(6) 0.0018(7) 0.0008(6)
C9 0.0352(9) 0.0394(9) 0.0633(11) 0.0090(8) 0.0039(8) -0.0056(7)
C10 0.0221(6) 0.0396(8) 0.0285(7) -0.0055(6) 0.0036(5) 0.0035(6)
C11 0.0264(7) 0.0647(11) 0.0342(8) -0.0146(8) 0.0018(6) -0.0030(8)
C12 0.0296(8) 0.0941(16) 0.0277(8) 0.0006(9) -0.0031(6) 0.0103(9)
C13 0.0360(9) 0.0765(13) 0.0346(8) 0.0215(9) 0.0027(7) 0.0181(9)
C14 0.0309(8) 0.0447(9) 0.0357(8) 0.0124(7) 0.0053(6) 0.0074(7)
C15 0.0217(6) 0.0334(7) 0.0231(6) 0.0003(6) 0.0038(5) 0.0049(6)

_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 C6 1.4123(18) . ?
F2 C11 1.361(2) . ?
O1 C1 1.2021(19) . ?
C1 C2 1.514(2) . ?
C1 C5 1.543(2) . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.534(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5501(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C15 1.5148(19) . ?
C5 C6 1.5320(19) . ?
C6 C7 1.502(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.532(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.517(2) . ?
C8 C9 1.539(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.392(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.363(3) . ?
C12 C13 1.373(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(2) . ?
C14 H14 0.9500 . ?

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
O1 C1 C2 125.53(14) . . ?
O1 C1 C5 125.15(14) . . ?
C2 C1 C5 109.27(12) . . ?
C1 C2 C3 106.38(14) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 C4 103.72(13) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 105.48(12) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
C15 C5 C6 111.65(12) . . ?
C15 C5 C1 113.10(12) . . ?
C6 C5 C1 107.81(11) . . ?
C15 C5 C4 113.07(11) . . ?
C6 C5 C4 108.92(11) . . ?
C1 C5 C4 101.73(11) . . ?
F1 C6 C7 108.83(13) . . ?
F1 C6 C5 108.61(12) . . ?
C7 C6 C5 112.64(13) . . ?
F1 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
C6 C7 C8 113.77(12) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C10 C8 C7 111.19(12) . . ?
C10 C8 C9 111.44(13) . . ?
C7 C8 C9 112.55(14) . . ?
C10 C8 H8 107.1 . . ?
C7 C8 H8 107.1 . . ?
C9 C8 H8 107.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 116.56(15) . . ?
C15 C10 C8 124.11(13) . . ?
C11 C10 C8 119.34(15) . . ?
F2 C11 C12 118.07(15) . . ?
F2 C11 C10 117.36(18) . . ?
C12 C11 C10 124.57(18) . . ?
C11 C12 C13 118.08(16) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C12 C13 C14 120.05(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 121.06(17) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 119.67(13) . . ?
C10 C15 C5 121.67(12) . . ?
C14 C15 C5 118.59(13) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 1015665'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FR1180

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 Br O'
_chemical_formula_sum            'C16 H19 Br O'
_chemical_formula_weight         307.22
_chemical_absolute_configuration ad

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.28437(12)
_cell_length_b                   7.79577(13)
_cell_length_c                   24.4543(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1388.69(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5444
_cell_measurement_theta_min      5.3720
_cell_measurement_theta_max      72.4820

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3171
_exptl_crystal_size_mid          0.2338
_exptl_crystal_size_min          0.0949
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    3.904
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_T_max  0.724
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(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_detector_area_resol_mean 10.4679
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6355
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         72.58
_reflns_number_total             2690
_reflns_number_gt                2667
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  ShelX_Acta

_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)+(0.0550P)²+0.1080P] 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   -0.013(18)
_refine_ls_number_reflns         2690
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.69624(3) -0.01292(3) 0.744819(9) 0.03670(10) Uani 1 1 d . . .
O2 O 0.7117(2) -0.0696(2) 0.59490(7) 0.0401(4) Uani 1 1 d . . .
C3 C 0.5276(3) 0.1344(3) 0.64758(8) 0.0236(4) Uani 1 1 d . . .
C4 C 0.6681(3) 0.1796(3) 0.69203(8) 0.0250(4) Uani 1 1 d . . .
H4 H 0.6213 0.2817 0.7125 0.030 Uiso 1 1 calc R . .
C5 C 0.5352(3) 0.2695(3) 0.60218(8) 0.0255(4) Uani 1 1 d . . .
C6 C 0.5747(3) -0.0420(3) 0.62088(8) 0.0279(4) Uani 1 1 d . . .
C7 C 0.8556(3) 0.2226(3) 0.66999(10) 0.0320(5) Uani 1 1 d . . .
H7A H 0.9032 0.1248 0.6484 0.038 Uiso 1 1 calc R . .
H7B H 0.9412 0.2436 0.7007 0.038 Uiso 1 1 calc R . .
C8 C 0.5432(4) 0.4837(3) 0.51142(8) 0.0439(6) Uani 1 1 d . . .
H8 H 0.5458 0.5566 0.4803 0.053 Uiso 1 1 calc R . .
C9 C 0.3862(4) 0.2770(3) 0.56557(9) 0.0342(5) Uani 1 1 d . . .
H9 H 0.2816 0.2067 0.5717 0.041 Uiso 1 1 calc R . .
C10 C 0.4228(3) -0.1686(3) 0.63203(10) 0.0361(5) Uani 1 1 d . . .
H10A H 0.4562 -0.2454 0.6627 0.043 Uiso 1 1 calc R . .
H10B H 0.3980 -0.2394 0.5992 0.043 Uiso 1 1 calc R . .
C11 C 0.3901(4) 0.3850(3) 0.52091(9) 0.0416(6) Uani 1 1 d . . .
H11 H 0.2878 0.3911 0.4969 0.050 Uiso 1 1 calc R . .
C12 C 0.6886(3) 0.3738(2) 0.59290(8) 0.0274(4) Uani 1 1 d . . .
C13 C 0.6939(4) 0.4797(3) 0.54602(9) 0.0362(5) Uani 1 1 d . . .
C14 C 0.3332(3) 0.1061(3) 0.67172(8) 0.0286(4) Uani 1 1 d . . .
H14A H 0.3399 0.0960 0.7120 0.034 Uiso 1 1 calc R . .
H14B H 0.2526 0.2042 0.6625 0.034 Uiso 1 1 calc R . .
C15 C 0.8450(3) 0.3825(3) 0.63377(10) 0.0317(5) Uani 1 1 d . . .
H15 H 0.9623 0.3903 0.6127 0.038 Uiso 1 1 calc R . .
C16 C 0.8289(3) 0.5451(3) 0.66918(10) 0.0379(5) Uani 1 1 d . . .
H16A H 0.7108 0.5446 0.6884 0.057 Uiso 1 1 calc R . .
H16B H 0.8366 0.6468 0.6458 0.057 Uiso 1 1 calc R . .
H16C H 0.9291 0.5473 0.6959 0.057 Uiso 1 1 calc R . .
C17 C 0.8616(4) 0.5835(3) 0.53190(12) 0.0489(7) Uani 1 1 d . . .
H17A H 0.9652 0.5062 0.5251 0.073 Uiso 1 1 calc R . .
H17B H 0.8915 0.6601 0.5624 0.073 Uiso 1 1 calc R . .
H17C H 0.8372 0.6518 0.4990 0.073 Uiso 1 1 calc R . .
C18 C 0.2565(3) -0.0610(3) 0.64662(11) 0.0368(5) Uani 1 1 d . . .
H18A H 0.1779 -0.1220 0.6733 0.044 Uiso 1 1 calc R . .
H18B H 0.1828 -0.0356 0.6136 0.044 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
Br1 0.03321(15) 0.04239(15) 0.03448(14) 0.01619(9) -0.00703(8) -0.00213(8)
O2 0.0447(9) 0.0323(8) 0.0432(9) 0.0033(7) 0.0202(8) 0.0111(7)
C3 0.0208(9) 0.0265(10) 0.0234(9) 0.0012(8) 0.0020(7) 0.0045(7)
C4 0.0222(10) 0.0266(9) 0.0261(9) 0.0065(7) -0.0003(8) 0.0026(8)
C5 0.0294(10) 0.0246(9) 0.0226(9) -0.0021(7) -0.0004(8) 0.0096(8)
C6 0.0335(10) 0.0253(9) 0.0248(8) 0.0035(8) 0.0014(8) 0.0066(9)
C7 0.0191(10) 0.0330(11) 0.0440(12) 0.0069(10) 0.0030(9) 0.0033(8)
C8 0.0791(17) 0.0281(11) 0.0245(9) 0.0043(10) 0.0076(11) 0.0196(12)
C9 0.0407(13) 0.0323(11) 0.0295(10) -0.0001(9) -0.0065(10) 0.0081(9)
C10 0.0410(13) 0.0288(11) 0.0385(11) -0.0006(9) 0.0009(11) -0.0013(9)
C11 0.0595(16) 0.0389(12) 0.0264(10) -0.0002(10) -0.0091(11) 0.0169(12)
C12 0.0333(11) 0.0235(9) 0.0254(9) 0.0002(7) 0.0093(9) 0.0077(9)
C13 0.0561(14) 0.0228(9) 0.0296(10) 0.0013(8) 0.0152(9) 0.0101(11)
C14 0.0213(10) 0.0360(11) 0.0286(9) -0.0018(8) 0.0005(8) 0.0026(8)
C15 0.0217(10) 0.0305(11) 0.0428(11) 0.0064(9) 0.0082(9) 0.0037(8)
C16 0.0369(12) 0.0331(11) 0.0436(12) 0.0010(10) -0.0094(10) -0.0023(10)
C17 0.0695(19) 0.0322(11) 0.0450(13) 0.0081(11) 0.0294(14) 0.0016(12)
C18 0.0293(11) 0.0381(12) 0.0429(12) -0.0013(10) -0.0031(9) -0.0046(9)

_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
Br1 C4 1.9901(19) . ?
O2 C6 1.202(3) . ?
C3 C5 1.532(3) . ?
C3 C4 1.534(3) . ?
C3 C14 1.550(3) . ?
C3 C6 1.561(3) . ?
C4 C7 1.507(3) . ?
C4 H4 1.0000 . ?
C5 C12 1.400(3) . ?
C5 C9 1.409(3) . ?
C6 C10 1.508(3) . ?
C7 C15 1.531(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C11 1.375(4) . ?
C8 C13 1.387(4) . ?
C8 H8 0.9500 . ?
C9 C11 1.379(3) . ?
C9 H9 0.9500 . ?
C10 C18 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 0.9500 . ?
C12 C13 1.413(3) . ?
C12 C15 1.517(3) . ?
C13 C17 1.505(4) . ?
C14 C18 1.545(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.540(3) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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 C3 C4 109.37(17) . . ?
C5 C3 C14 114.00(17) . . ?
C4 C3 C14 111.84(16) . . ?
C5 C3 C6 107.16(16) . . ?
C4 C3 C6 110.64(16) . . ?
C14 C3 C6 103.60(17) . . ?
C7 C4 C3 113.73(17) . . ?
C7 C4 Br1 107.85(13) . . ?
C3 C4 Br1 110.81(14) . . ?
C7 C4 H4 108.1 . . ?
C3 C4 H4 108.1 . . ?
Br1 C4 H4 108.1 . . ?
C12 C5 C9 119.2(2) . . ?
C12 C5 C3 123.08(18) . . ?
C9 C5 C3 117.5(2) . . ?
O2 C6 C10 126.0(2) . . ?
O2 C6 C3 124.1(2) . . ?
C10 C6 C3 109.87(17) . . ?
C4 C7 C15 110.03(17) . . ?
C4 C7 H7A 109.7 . . ?
C15 C7 H7A 109.7 . . ?
C4 C7 H7B 109.7 . . ?
C15 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C11 C8 C13 121.8(2) . . ?
C11 C8 H8 119.1 . . ?
C13 C8 H8 119.1 . . ?
C11 C9 C5 120.8(2) . . ?
C11 C9 H9 119.6 . . ?
C5 C9 H9 119.6 . . ?
C6 C10 C18 105.48(19) . . ?
C6 C10 H10A 110.6 . . ?
C18 C10 H10A 110.6 . . ?
C6 C10 H10B 110.6 . . ?
C18 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
C8 C11 C9 119.5(2) . . ?
C8 C11 H11 120.3 . . ?
C9 C11 H11 120.3 . . ?
C5 C12 C13 119.5(2) . . ?
C5 C12 C15 121.21(17) . . ?
C13 C12 C15 119.2(2) . . ?
C8 C13 C12 119.1(2) . . ?
C8 C13 C17 119.4(2) . . ?
C12 C13 C17 121.5(2) . . ?
C18 C14 C3 107.39(18) . . ?
C18 C14 H14A 110.2 . . ?
C3 C14 H14A 110.2 . . ?
C18 C14 H14B 110.2 . . ?
C3 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C12 C15 C7 112.51(18) . . ?
C12 C15 C16 110.50(18) . . ?
C7 C15 C16 110.40(19) . . ?
C12 C15 H15 107.7 . . ?
C7 C15 H15 107.7 . . ?
C16 C15 H15 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 C14 105.73(18) . . ?
C10 C18 H18A 110.6 . . ?
C14 C18 H18A 110.6 . . ?
C10 C18 H18B 110.6 . . ?
C14 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        72.58
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.082

#===END
_database_code_depnum_ccdc_archive 'CCDC 1015666'
