# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 910029'
#TrackingRef 'shelxl.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 Br O4'
_chemical_formula_weight         413.26
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   P6(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'
_cell_length_a                   14.959(2)
_cell_length_b                   14.959(2)
_cell_length_c                   14.020(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2717.1(8)
_cell_formula_units_Z            6
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    7302
_cell_measurement_theta_min      1.5719
_cell_measurement_theta_max      27.8346
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1260
_exptl_absorpt_coefficient_mu    2.293
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_T_max  0.8032
_exptl_absorpt_process_details   crystalclear
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22900
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         27.88
_reflns_number_total             4299
_reflns_number_gt                3967
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0180P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0094(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(6)
_refine_ls_number_reflns         4299
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.002
_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 0.83799(2) 0.73699(2) 0.100258(19) 0.03098(9) Uani 1 1 d . . .
O1 O 0.55881(13) 0.60363(13) -0.02427(12) 0.0205(4) Uani 1 1 d . . .
O2 O 0.64236(13) 0.51446(14) -0.00909(13) 0.0235(4) Uani 1 1 d . . .
O3 O 0.39418(13) 0.34368(13) 0.01437(14) 0.0262(4) Uani 1 1 d . . .
O4 O 0.37966(14) 0.23290(12) 0.13066(13) 0.0254(4) Uani 1 1 d . . .
C1 C 0.75115(18) 0.76631(19) 0.17712(18) 0.0205(5) Uani 1 1 d . . .
C2 C 0.7822(2) 0.86998(19) 0.1905(2) 0.0270(6) Uani 1 1 d . . .
H2 H 0.8433 0.9218 0.1606 0.032 Uiso 1 1 calc R . .
C3 C 0.7247(2) 0.8977(2) 0.2467(2) 0.0263(6) Uani 1 1 d . . .
H3 H 0.7454 0.9684 0.2553 0.032 Uiso 1 1 calc R . .
C4 C 0.6367(2) 0.8217(2) 0.29050(19) 0.0250(6) Uani 1 1 d . . .
H4 H 0.5966 0.8405 0.3294 0.030 Uiso 1 1 calc R . .
C5 C 0.60618(19) 0.71850(19) 0.27831(17) 0.0208(5) Uani 1 1 d . . .
H5 H 0.5460 0.6675 0.3099 0.025 Uiso 1 1 calc R . .
C6 C 0.66229(18) 0.68739(18) 0.22027(17) 0.0179(5) Uani 1 1 d . . .
C7 C 0.62649(18) 0.57471(18) 0.20353(17) 0.0186(5) Uani 1 1 d . . .
H7 H 0.6878 0.5711 0.1801 0.022 Uiso 1 1 calc R . .
C8 C 0.5844(2) 0.50260(18) 0.29114(18) 0.0242(6) Uani 1 1 d . . .
H8A H 0.6407 0.4999 0.3259 0.029 Uiso 1 1 calc R . .
H8B H 0.5481 0.5252 0.3355 0.029 Uiso 1 1 calc R . .
C9 C 0.51160(18) 0.40067(19) 0.24746(18) 0.0202(5) Uani 1 1 d . . .
H9 H 0.4842 0.3368 0.2804 0.024 Uiso 1 1 calc R . .
C10 C 0.48924(18) 0.40920(18) 0.15696(18) 0.0186(5) Uani 1 1 d . . .
C11 C 0.53979(17) 0.52068(17) 0.12577(17) 0.0160(5) Uani 1 1 d . . .
C12 C 0.46449(17) 0.55975(17) 0.11562(16) 0.0156(5) Uani 1 1 d . . .
C13 C 0.38515(17) 0.55037(18) 0.17329(18) 0.0192(5) Uani 1 1 d . . .
H13 H 0.3710 0.5157 0.2329 0.023 Uiso 1 1 calc R . .
C14 C 0.32672(18) 0.59334(19) 0.14110(19) 0.0215(5) Uani 1 1 d . . .
H14 H 0.2720 0.5880 0.1796 0.026 Uiso 1 1 calc R . .
C15 C 0.3466(2) 0.64357(19) 0.05430(19) 0.0231(5) Uani 1 1 d . . .
H15 H 0.3055 0.6722 0.0343 0.028 Uiso 1 1 calc R . .
C16 C 0.42622(19) 0.65296(18) -0.00452(18) 0.0229(5) Uani 1 1 d . . .
H16 H 0.4412 0.6881 -0.0639 0.028 Uiso 1 1 calc R . .
C17 C 0.48174(18) 0.60868(18) 0.02813(18) 0.0181(5) Uani 1 1 d . . .
C18 C 0.58713(18) 0.54210(17) 0.02563(17) 0.0179(5) Uani 1 1 d . . .
C19 C 0.41686(17) 0.32713(17) 0.09298(19) 0.0187(5) Uani 1 1 d . . .
C20 C 0.3048(2) 0.1473(2) 0.0738(2) 0.0297(6) Uani 1 1 d . . .
H20A H 0.3363 0.1426 0.0133 0.036 Uiso 1 1 calc R . .
H20B H 0.2450 0.1561 0.0588 0.036 Uiso 1 1 calc R . .
C21 C 0.2716(3) 0.0527(2) 0.1325(2) 0.0418(8) Uani 1 1 d . . .
H21A H 0.3317 0.0454 0.1472 0.063 Uiso 1 1 calc R . .
H21B H 0.2209 -0.0080 0.0968 0.063 Uiso 1 1 calc R . .
H21C H 0.2405 0.0584 0.1920 0.063 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 0.02467(14) 0.03321(16) 0.03175(16) 0.00004(13) 0.00837(12) 0.01199(12)
O1 0.0254(9) 0.0237(9) 0.0153(9) 0.0019(7) 0.0011(7) 0.0146(8)
O2 0.0250(9) 0.0260(9) 0.0224(10) -0.0002(8) 0.0051(8) 0.0148(8)
O3 0.0278(9) 0.0257(9) 0.0247(10) 0.0008(8) -0.0052(9) 0.0132(8)
O4 0.0293(9) 0.0163(8) 0.0238(10) 0.0009(7) -0.0034(8) 0.0063(7)
C1 0.0197(12) 0.0260(13) 0.0176(12) 0.0007(11) -0.0020(10) 0.0127(10)
C2 0.0305(14) 0.0211(13) 0.0251(15) 0.0023(11) -0.0044(12) 0.0096(11)
C3 0.0369(15) 0.0195(13) 0.0235(15) -0.0020(11) -0.0053(12) 0.0148(12)
C4 0.0318(14) 0.0303(14) 0.0211(14) -0.0067(11) -0.0071(11) 0.0217(12)
C5 0.0205(12) 0.0261(12) 0.0160(13) -0.0020(11) -0.0026(10) 0.0118(10)
C6 0.0205(12) 0.0214(12) 0.0135(12) -0.0006(10) -0.0042(10) 0.0117(10)
C7 0.0201(12) 0.0221(12) 0.0154(12) 0.0004(10) -0.0005(10) 0.0119(10)
C8 0.0293(14) 0.0241(13) 0.0184(14) 0.0018(10) -0.0049(10) 0.0127(11)
C9 0.0203(12) 0.0208(12) 0.0188(14) 0.0028(10) 0.0004(10) 0.0097(10)
C10 0.0180(11) 0.0195(12) 0.0210(13) 0.0028(10) 0.0032(10) 0.0114(10)
C11 0.0164(11) 0.0174(11) 0.0164(12) 0.0006(9) 0.0014(9) 0.0102(9)
C12 0.0179(11) 0.0158(11) 0.0145(13) -0.0010(9) -0.0031(9) 0.0095(9)
C13 0.0178(12) 0.0202(12) 0.0189(13) 0.0005(10) 0.0011(10) 0.0089(10)
C14 0.0176(12) 0.0213(12) 0.0286(15) -0.0066(11) -0.0024(11) 0.0120(10)
C15 0.0254(13) 0.0209(12) 0.0273(15) -0.0043(11) -0.0069(11) 0.0149(11)
C16 0.0300(14) 0.0209(12) 0.0201(14) -0.0004(10) -0.0060(11) 0.0144(11)
C17 0.0195(12) 0.0181(11) 0.0172(12) -0.0022(10) -0.0012(10) 0.0098(10)
C18 0.0172(11) 0.0166(11) 0.0161(12) -0.0023(10) -0.0030(10) 0.0057(10)
C19 0.0172(11) 0.0207(11) 0.0206(13) 0.0001(11) 0.0013(11) 0.0114(9)
C20 0.0284(14) 0.0218(13) 0.0307(16) -0.0050(12) 0.0003(12) 0.0066(11)
C21 0.0517(19) 0.0232(14) 0.0395(19) 0.0006(13) 0.0071(15) 0.0104(14)
_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 C1 1.900(2) . ?
O1 C18 1.381(3) . ?
O1 C17 1.401(3) . ?
O2 C18 1.197(3) . ?
O3 C19 1.215(3) . ?
O4 C19 1.338(3) . ?
O4 C20 1.447(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.399(3) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(3) . ?
C7 C8 1.546(3) . ?
C7 C11 1.573(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.492(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.334(3) . ?
C9 H9 0.9500 . ?
C10 C19 1.468(3) . ?
C10 C11 1.511(3) . ?
C11 C12 1.513(3) . ?
C11 C18 1.532(3) . ?
C12 C13 1.384(3) . ?
C12 C17 1.385(3) . ?
C13 C14 1.394(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(3) . ?
C16 H16 0.9500 . ?
C20 C21 1.491(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C18 O1 C17 107.78(18) . . ?
C19 O4 C20 116.4(2) . . ?
C2 C1 C6 122.0(2) . . ?
C2 C1 Br1 116.60(19) . . ?
C6 C1 Br1 121.41(18) . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 116.4(2) . . ?
C1 C6 C7 122.1(2) . . ?
C5 C6 C7 121.5(2) . . ?
C6 C7 C8 116.7(2) . . ?
C6 C7 C11 114.97(19) . . ?
C8 C7 C11 104.40(19) . . ?
C6 C7 H7 106.7 . . ?
C8 C7 H7 106.7 . . ?
C11 C7 H7 106.7 . . ?
C9 C8 C7 102.80(19) . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C8 112.5(2) . . ?
C10 C9 H9 123.8 . . ?
C8 C9 H9 123.8 . . ?
C9 C10 C19 128.1(2) . . ?
C9 C10 C11 111.7(2) . . ?
C19 C10 C11 119.9(2) . . ?
C10 C11 C12 113.28(18) . . ?
C10 C11 C18 114.82(19) . . ?
C12 C11 C18 100.88(19) . . ?
C10 C11 C7 101.27(19) . . ?
C12 C11 C7 116.64(19) . . ?
C18 C11 C7 110.56(18) . . ?
C13 C12 C17 119.7(2) . . ?
C13 C12 C11 132.2(2) . . ?
C17 C12 C11 108.0(2) . . ?
C12 C13 C14 117.9(2) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 116.4(2) . . ?
C17 C16 H16 121.8 . . ?
C15 C16 H16 121.8 . . ?
C16 C17 C12 123.5(2) . . ?
C16 C17 O1 124.3(2) . . ?
C12 C17 O1 112.1(2) . . ?
O2 C18 O1 121.3(2) . . ?
O2 C18 C11 128.8(2) . . ?
O1 C18 C11 109.86(19) . . ?
O3 C19 O4 124.2(2) . . ?
O3 C19 C10 123.3(2) . . ?
O4 C19 C10 112.6(2) . . ?
O4 C20 C21 106.2(2) . . ?
O4 C20 H20A 110.5 . . ?
C21 C20 H20A 110.5 . . ?
O4 C20 H20B 110.5 . . ?
C21 C20 H20B 110.5 . . ?
H20A C20 H20B 108.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C6 C1 C2 C3 -0.6(4) . . . . ?
Br1 C1 C2 C3 -178.7(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
Br1 C1 C6 C5 177.72(18) . . . . ?
C2 C1 C6 C7 178.0(2) . . . . ?
Br1 C1 C6 C7 -3.9(3) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C4 C5 C6 C7 -177.3(2) . . . . ?
C1 C6 C7 C8 139.7(2) . . . . ?
C5 C6 C7 C8 -42.0(3) . . . . ?
C1 C6 C7 C11 -97.5(3) . . . . ?
C5 C6 C7 C11 80.7(3) . . . . ?
C6 C7 C8 C9 152.8(2) . . . . ?
C11 C7 C8 C9 24.8(2) . . . . ?
C7 C8 C9 C10 -14.3(3) . . . . ?
C8 C9 C10 C19 -176.5(2) . . . . ?
C8 C9 C10 C11 -3.0(3) . . . . ?
C9 C10 C11 C12 -107.1(2) . . . . ?
C19 C10 C11 C12 66.9(3) . . . . ?
C9 C10 C11 C18 137.7(2) . . . . ?
C19 C10 C11 C18 -48.2(3) . . . . ?
C9 C10 C11 C7 18.6(3) . . . . ?
C19 C10 C11 C7 -167.4(2) . . . . ?
C6 C7 C11 C10 -155.18(19) . . . . ?
C8 C7 C11 C10 -26.1(2) . . . . ?
C6 C7 C11 C12 -31.8(3) . . . . ?
C8 C7 C11 C12 97.4(2) . . . . ?
C6 C7 C11 C18 82.7(2) . . . . ?
C8 C7 C11 C18 -148.21(19) . . . . ?
C10 C11 C12 C13 45.4(4) . . . . ?
C18 C11 C12 C13 168.7(2) . . . . ?
C7 C11 C12 C13 -71.6(3) . . . . ?
C10 C11 C12 C17 -131.2(2) . . . . ?
C18 C11 C12 C17 -8.0(2) . . . . ?
C7 C11 C12 C17 111.8(2) . . . . ?
C17 C12 C13 C14 -1.4(3) . . . . ?
C11 C12 C13 C14 -177.8(2) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C12 -2.1(4) . . . . ?
C15 C16 C17 O1 174.9(2) . . . . ?
C13 C12 C17 C16 2.5(4) . . . . ?
C11 C12 C17 C16 179.7(2) . . . . ?
C13 C12 C17 O1 -174.9(2) . . . . ?
C11 C12 C17 O1 2.2(3) . . . . ?
C18 O1 C17 C16 -172.0(2) . . . . ?
C18 O1 C17 C12 5.4(3) . . . . ?
C17 O1 C18 O2 170.4(2) . . . . ?
C17 O1 C18 C11 -10.7(2) . . . . ?
C10 C11 C18 O2 -47.7(3) . . . . ?
C12 C11 C18 O2 -169.8(2) . . . . ?
C7 C11 C18 O2 66.1(3) . . . . ?
C10 C11 C18 O1 133.6(2) . . . . ?
C12 C11 C18 O1 11.5(2) . . . . ?
C7 C11 C18 O1 -112.6(2) . . . . ?
C20 O4 C19 O3 -2.5(3) . . . . ?
C20 O4 C19 C10 177.9(2) . . . . ?
C9 C10 C19 O3 172.8(3) . . . . ?
C11 C10 C19 O3 -0.2(3) . . . . ?
C9 C10 C19 O4 -7.7(4) . . . . ?
C11 C10 C19 O4 179.4(2) . . . . ?
C19 O4 C20 C21 -177.2(2) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.063


data_shelx
_database_code_depnum_ccdc_archive 'CCDC 912219'
#TrackingRef 'shelx.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 Cl O6'
_chemical_formula_weight         420.87
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.254(4)
_cell_length_b                   10.490(5)
_cell_length_c                   11.773(5)
_cell_angle_alpha                90.722(6)
_cell_angle_beta                 91.612(6)
_cell_angle_gamma                112.650(9)
_cell_volume                     1053.9(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3558
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.9
_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   CrystalClear
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 14.22
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11133
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.87
_reflns_number_total             4965
_reflns_number_gt                3052
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         4965
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
Cl1 Cl 0.50158(4) 1.15416(3) 0.38804(3) 0.03433(11) Uani 1 1 d . . .
O1 O -0.07783(10) 0.67123(9) 0.30341(8) 0.0234(2) Uani 1 1 d . . .
O2 O 0.12872(11) 0.73741(9) 0.04676(8) 0.0299(2) Uani 1 1 d . . .
O3 O -0.05092(12) 0.34707(10) 0.33060(8) 0.0319(3) Uani 1 1 d . . .
O4 O 0.15609(11) 0.52828(9) 0.26630(8) 0.0272(2) Uani 1 1 d . . .
O5 O -0.36440(12) 0.74415(10) 0.03304(10) 0.0451(3) Uani 1 1 d . . .
O6 O -0.13645(11) 0.86190(9) 0.12934(8) 0.0289(2) Uani 1 1 d . . .
C1 C 0.05506(15) 0.78650(12) 0.32908(11) 0.0216(3) Uani 1 1 d . . .
C2 C 0.08440(17) 0.85185(13) 0.43480(12) 0.0254(3) Uani 1 1 d . . .
H2 H 0.0128 0.8186 0.4941 0.031 Uiso 1 1 calc R . .
C3 C 0.22195(17) 0.96768(14) 0.45143(12) 0.0264(3) Uani 1 1 d . . .
C4 C 0.32623(16) 1.01113(13) 0.36167(12) 0.0246(3) Uani 1 1 d . . .
C5 C 0.29867(15) 0.94709(13) 0.25484(12) 0.0226(3) Uani 1 1 d . . .
C6 C 0.15675(15) 0.83155(13) 0.24055(11) 0.0204(3) Uani 1 1 d . . .
C7 C 0.25733(19) 1.04390(15) 0.56528(13) 0.0384(4) Uani 1 1 d . . .
H7A H 0.1744 0.9955 0.6176 0.058 Uiso 1 1 calc R . .
H7B H 0.2625 1.1382 0.5554 0.058 Uiso 1 1 calc R . .
H7C H 0.3581 1.0474 0.5966 0.058 Uiso 1 1 calc R . .
C8 C 0.41155(16) 0.99483(15) 0.16027(13) 0.0320(4) Uani 1 1 d . . .
H8A H 0.4029 1.0763 0.1259 0.048 Uiso 1 1 calc R . .
H8B H 0.3867 0.9207 0.1025 0.048 Uiso 1 1 calc R . .
H8C H 0.5186 1.0187 0.1908 0.048 Uiso 1 1 calc R . .
C9 C 0.08438(16) 0.73856(13) 0.14305(12) 0.0225(3) Uani 1 1 d . . .
C10 C -0.07081(16) 0.63234(13) 0.18400(11) 0.0228(3) Uani 1 1 d . . .
C11 C -0.21989(16) 0.62339(14) 0.12188(12) 0.0263(3) Uani 1 1 d . . .
C12 C -0.32147(18) 0.49341(15) 0.11069(12) 0.0319(4) Uani 1 1 d . . .
H12 H -0.4228 0.4670 0.0755 0.038 Uiso 1 1 calc R . .
C13 C -0.25918(17) 0.39326(14) 0.15952(13) 0.0306(4) Uani 1 1 d . . .
H13A H -0.2793 0.3134 0.1069 0.037 Uiso 1 1 calc R . .
H13B H -0.3055 0.3595 0.2335 0.037 Uiso 1 1 calc R . .
C14 C -0.08374(16) 0.48125(13) 0.17371(12) 0.0240(3) Uani 1 1 d . . .
H14 H -0.0353 0.4724 0.1007 0.029 Uiso 1 1 calc R . .
C15 C 0.00502(17) 0.44196(13) 0.26761(12) 0.0247(3) Uani 1 1 d . . .
C16 C 0.27777(17) 0.51732(14) 0.34618(13) 0.0309(4) Uani 1 1 d . . .
C17 C 0.2369(2) 0.53648(16) 0.46734(13) 0.0409(4) Uani 1 1 d . . .
H17A H 0.2218 0.6237 0.4748 0.061 Uiso 1 1 calc R . .
H17B H 0.3223 0.5386 0.5195 0.061 Uiso 1 1 calc R . .
H17C H 0.1401 0.4596 0.4861 0.061 Uiso 1 1 calc R . .
C18 C 0.42354(17) 0.63663(15) 0.31109(15) 0.0417(4) Uani 1 1 d . . .
H18A H 0.4401 0.6259 0.2303 0.063 Uiso 1 1 calc R . .
H18B H 0.5144 0.6372 0.3562 0.063 Uiso 1 1 calc R . .
H18C H 0.4103 0.7239 0.3241 0.063 Uiso 1 1 calc R . .
C19 C 0.29288(19) 0.37974(15) 0.32548(16) 0.0477(5) Uani 1 1 d . . .
H19A H 0.1978 0.3045 0.3494 0.071 Uiso 1 1 calc R . .
H19B H 0.3838 0.3782 0.3693 0.071 Uiso 1 1 calc R . .
H19C H 0.3068 0.3678 0.2444 0.071 Uiso 1 1 calc R . .
C20 C -0.25171(17) 0.74635(14) 0.08893(13) 0.0301(4) Uani 1 1 d . . .
C21 C -0.15075(18) 0.99271(14) 0.10703(14) 0.0352(4) Uani 1 1 d . . .
H21A H -0.2454 0.9955 0.1423 0.042 Uiso 1 1 calc R . .
H21B H -0.1594 1.0046 0.0242 0.042 Uiso 1 1 calc R . .
C22 C -0.00657(19) 1.10470(14) 0.15732(13) 0.0377(4) Uani 1 1 d . . .
H22A H 0.0012 1.0911 0.2391 0.056 Uiso 1 1 calc R . .
H22B H -0.0126 1.1947 0.1448 0.056 Uiso 1 1 calc R . .
H22C H 0.0860 1.1016 0.1210 0.056 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
Cl1 0.0259(2) 0.02412(19) 0.0469(2) -0.00195(16) -0.00952(18) 0.00369(16)
O1 0.0212(5) 0.0224(5) 0.0217(5) 0.0009(4) 0.0019(4) 0.0027(4)
O2 0.0308(6) 0.0317(6) 0.0227(5) 0.0021(4) 0.0032(5) 0.0067(5)
O3 0.0369(6) 0.0250(5) 0.0309(6) 0.0051(5) 0.0013(5) 0.0088(5)
O4 0.0236(6) 0.0264(5) 0.0290(6) 0.0026(4) -0.0032(5) 0.0070(4)
O5 0.0299(7) 0.0407(6) 0.0600(8) 0.0079(6) -0.0179(6) 0.0095(5)
O6 0.0254(6) 0.0258(5) 0.0338(6) 0.0021(4) -0.0057(5) 0.0086(5)
C1 0.0198(7) 0.0193(7) 0.0251(7) 0.0017(6) -0.0024(6) 0.0072(6)
C2 0.0276(8) 0.0262(7) 0.0228(7) 0.0014(6) 0.0012(6) 0.0107(7)
C3 0.0304(8) 0.0239(7) 0.0266(8) -0.0003(6) -0.0045(7) 0.0128(7)
C4 0.0207(8) 0.0181(7) 0.0339(8) 0.0007(6) -0.0068(6) 0.0069(6)
C5 0.0192(7) 0.0214(7) 0.0286(8) 0.0048(6) -0.0008(6) 0.0094(6)
C6 0.0186(7) 0.0200(7) 0.0224(7) 0.0035(6) 0.0001(6) 0.0071(6)
C7 0.0415(10) 0.0357(9) 0.0336(9) -0.0097(7) -0.0056(8) 0.0109(8)
C8 0.0211(8) 0.0331(8) 0.0366(9) 0.0036(7) 0.0013(7) 0.0046(7)
C9 0.0214(8) 0.0232(7) 0.0227(7) 0.0048(6) 0.0003(6) 0.0086(6)
C10 0.0231(8) 0.0243(7) 0.0176(7) 0.0015(6) -0.0001(6) 0.0055(6)
C11 0.0212(8) 0.0280(7) 0.0255(8) 0.0022(6) -0.0029(6) 0.0051(6)
C12 0.0248(8) 0.0362(8) 0.0287(8) 0.0008(7) -0.0052(7) 0.0057(7)
C13 0.0287(9) 0.0268(8) 0.0289(8) 0.0003(6) -0.0022(7) 0.0028(7)
C14 0.0243(8) 0.0220(7) 0.0216(7) 0.0002(6) -0.0001(6) 0.0044(6)
C15 0.0293(8) 0.0208(7) 0.0232(8) -0.0032(6) 0.0019(6) 0.0087(7)
C16 0.0289(9) 0.0281(8) 0.0365(9) -0.0016(7) -0.0094(7) 0.0125(7)
C17 0.0471(11) 0.0385(9) 0.0326(9) -0.0018(7) -0.0116(8) 0.0127(8)
C18 0.0288(9) 0.0391(9) 0.0548(11) -0.0009(8) -0.0066(8) 0.0111(8)
C19 0.0390(11) 0.0343(9) 0.0729(13) -0.0103(9) -0.0144(10) 0.0191(8)
C20 0.0217(8) 0.0329(8) 0.0317(9) 0.0037(7) -0.0018(7) 0.0061(7)
C21 0.0348(9) 0.0326(8) 0.0439(10) 0.0004(7) -0.0017(8) 0.0195(7)
C22 0.0500(11) 0.0318(8) 0.0321(9) -0.0046(7) -0.0024(8) 0.0173(8)
_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
Cl1 C4 1.7507(15) . ?
O1 C1 1.3748(16) . ?
O1 C10 1.4690(16) . ?
O2 C9 1.2179(17) . ?
O3 C15 1.2049(16) . ?
O4 C15 1.3420(17) . ?
O4 C16 1.4860(16) . ?
O5 C20 1.2096(16) . ?
O6 C20 1.3395(17) . ?
O6 C21 1.4547(17) . ?
C1 C2 1.3816(18) . ?
C1 C6 1.3858(19) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(2) . ?
C3 C7 1.5132(19) . ?
C4 C5 1.3880(19) . ?
C5 C6 1.4066(18) . ?
C5 C8 1.503(2) . ?
C6 C9 1.4638(18) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5350(19) . ?
C10 C11 1.5127(19) . ?
C10 C14 1.546(2) . ?
C11 C12 1.327(2) . ?
C11 C20 1.483(2) . ?
C12 C13 1.493(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.530(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5126(19) . ?
C14 H14 1.0000 . ?
C16 C17 1.517(2) . ?
C16 C18 1.517(2) . ?
C16 C19 1.520(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.497(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C1 O1 C10 107.41(10) . . ?
C15 O4 C16 122.70(11) . . ?
C20 O6 C21 117.53(11) . . ?
O1 C1 C2 122.51(13) . . ?
O1 C1 C6 114.62(12) . . ?
C2 C1 C6 122.87(13) . . ?
C1 C2 C3 117.75(14) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C4 119.01(13) . . ?
C2 C3 C7 119.49(14) . . ?
C4 C3 C7 121.50(13) . . ?
C5 C4 C3 124.07(13) . . ?
C5 C4 Cl1 118.49(12) . . ?
C3 C4 Cl1 117.45(11) . . ?
C4 C5 C6 115.28(13) . . ?
C4 C5 C8 123.27(13) . . ?
C6 C5 C8 121.44(12) . . ?
C1 C6 C5 121.00(12) . . ?
C1 C6 C9 106.77(12) . . ?
C5 C6 C9 132.23(13) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C6 130.88(13) . . ?
O2 C9 C10 123.07(12) . . ?
C6 C9 C10 106.04(12) . . ?
O1 C10 C11 108.46(11) . . ?
O1 C10 C9 105.14(10) . . ?
C11 C10 C9 117.41(11) . . ?
O1 C10 C14 110.54(11) . . ?
C11 C10 C14 101.49(10) . . ?
C9 C10 C14 113.76(12) . . ?
C12 C11 C20 125.19(13) . . ?
C12 C11 C10 111.19(12) . . ?
C20 C11 C10 123.36(11) . . ?
C11 C12 C13 112.63(13) . . ?
C11 C12 H12 123.7 . . ?
C13 C12 H12 123.7 . . ?
C12 C13 C14 102.14(11) . . ?
C12 C13 H13A 111.3 . . ?
C14 C13 H13A 111.3 . . ?
C12 C13 H13B 111.3 . . ?
C14 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
C15 C14 C13 116.61(12) . . ?
C15 C14 C10 113.48(11) . . ?
C13 C14 C10 105.52(11) . . ?
C15 C14 H14 106.9 . . ?
C13 C14 H14 106.9 . . ?
C10 C14 H14 106.9 . . ?
O3 C15 O4 126.33(13) . . ?
O3 C15 C14 125.34(13) . . ?
O4 C15 C14 108.31(12) . . ?
O4 C16 C17 109.51(12) . . ?
O4 C16 C18 101.92(11) . . ?
C17 C16 C18 111.69(13) . . ?
O4 C16 C19 109.31(11) . . ?
C17 C16 C19 112.80(14) . . ?
C18 C16 C19 111.03(14) . . ?
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 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 O6 124.30(13) . . ?
O5 C20 C11 125.49(13) . . ?
O6 C20 C11 110.20(12) . . ?
O6 C21 C22 107.10(12) . . ?
O6 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 . . ?
O6 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C10 O1 C1 C2 178.86(11) . . . . ?
C10 O1 C1 C6 -1.14(14) . . . . ?
O1 C1 C2 C3 -179.80(12) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C4 -1.48(19) . . . . ?
C1 C2 C3 C7 178.92(12) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C7 C3 C4 C5 -178.67(13) . . . . ?
C2 C3 C4 Cl1 -177.80(10) . . . . ?
C7 C3 C4 Cl1 1.80(17) . . . . ?
C3 C4 C5 C6 -0.59(19) . . . . ?
Cl1 C4 C5 C6 178.95(9) . . . . ?
C3 C4 C5 C8 -179.86(12) . . . . ?
Cl1 C4 C5 C8 -0.33(18) . . . . ?
O1 C1 C6 C5 -179.03(11) . . . . ?
C2 C1 C6 C5 0.97(19) . . . . ?
O1 C1 C6 C9 1.10(15) . . . . ?
C2 C1 C6 C9 -178.90(12) . . . . ?
C4 C5 C6 C1 -0.75(18) . . . . ?
C8 C5 C6 C1 178.54(12) . . . . ?
C4 C5 C6 C9 179.07(13) . . . . ?
C8 C5 C6 C9 -1.6(2) . . . . ?
C1 C6 C9 O2 179.39(14) . . . . ?
C5 C6 C9 O2 -0.5(3) . . . . ?
C1 C6 C9 C10 -0.58(14) . . . . ?
C5 C6 C9 C10 179.57(13) . . . . ?
C1 O1 C10 C11 -125.71(11) . . . . ?
C1 O1 C10 C9 0.67(13) . . . . ?
C1 O1 C10 C14 123.84(11) . . . . ?
O2 C9 C10 O1 179.97(12) . . . . ?
C6 C9 C10 O1 -0.05(14) . . . . ?
O2 C9 C10 C11 -59.37(18) . . . . ?
C6 C9 C10 C11 120.61(12) . . . . ?
O2 C9 C10 C14 58.89(17) . . . . ?
C6 C9 C10 C14 -121.13(12) . . . . ?
O1 C10 C11 C12 -99.41(14) . . . . ?
C9 C10 C11 C12 141.68(14) . . . . ?
C14 C10 C11 C12 17.04(16) . . . . ?
O1 C10 C11 C20 74.96(16) . . . . ?
C9 C10 C11 C20 -43.95(19) . . . . ?
C14 C10 C11 C20 -168.59(13) . . . . ?
C20 C11 C12 C13 -175.64(13) . . . . ?
C10 C11 C12 C13 -1.40(18) . . . . ?
C11 C12 C13 C14 -15.09(17) . . . . ?
C12 C13 C14 C15 151.78(12) . . . . ?
C12 C13 C14 C10 24.80(14) . . . . ?
O1 C10 C14 C15 -39.38(16) . . . . ?
C11 C10 C14 C15 -154.30(12) . . . . ?
C9 C10 C14 C15 78.64(15) . . . . ?
O1 C10 C14 C13 89.49(13) . . . . ?
C11 C10 C14 C13 -25.43(14) . . . . ?
C9 C10 C14 C13 -152.50(11) . . . . ?
C16 O4 C15 O3 -0.3(2) . . . . ?
C16 O4 C15 C14 -178.73(11) . . . . ?
C13 C14 C15 O3 0.7(2) . . . . ?
C10 C14 C15 O3 123.67(15) . . . . ?
C13 C14 C15 O4 179.12(11) . . . . ?
C10 C14 C15 O4 -57.93(15) . . . . ?
C15 O4 C16 C17 -60.90(16) . . . . ?
C15 O4 C16 C18 -179.29(12) . . . . ?
C15 O4 C16 C19 63.15(17) . . . . ?
C21 O6 C20 O5 1.9(2) . . . . ?
C21 O6 C20 C11 -178.60(12) . . . . ?
C12 C11 C20 O5 -11.4(3) . . . . ?
C10 C11 C20 O5 174.99(15) . . . . ?
C12 C11 C20 O6 169.03(15) . . . . ?
C10 C11 C20 O6 -4.5(2) . . . . ?
C20 O6 C21 C22 -178.31(13) . . . . ?
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.87
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.044


data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 917076'
#TrackingRef 'shelxl.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 F O4'
_chemical_formula_sum            'C21 H17 F O4'
_chemical_formula_weight         352.35
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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   11.757(4)
_cell_length_b                   5.943(2)
_cell_length_c                   25.700(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.394(6)
_cell_angle_gamma                90.00
_cell_volume                     1753.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1924
_cell_measurement_theta_min      27.70
_cell_measurement_theta_max      72.00
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8395
_exptl_absorpt_correction_T_max  0.8795
_exptl_absorpt_process_details   Crystalclear
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn944 CCD'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 11.11
_diffrn_reflns_number            23189
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         69.95
_reflns_number_total             3285
_reflns_number_gt                2805
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1240P)^2^+0.0698P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.118(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3285
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1780
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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 0.97275(10) 0.12603(18) 0.19564(4) 0.0684(4) Uani 1 1 d . . .
O1 O 0.90368(13) 0.3240(3) 0.01592(5) 0.0771(5) Uani 1 1 d . . .
O2 O 1.07834(12) 0.2530(2) 0.06646(5) 0.0681(4) Uani 1 1 d . . .
O3 O 0.60997(13) 0.3781(4) 0.11374(8) 0.1011(7) Uani 1 1 d . . .
O4 O 0.56762(12) 0.6930(3) 0.06725(7) 0.0883(6) Uani 1 1 d . . .
C1 C 0.97442(16) 0.3647(3) 0.05549(7) 0.0579(5) Uani 1 1 d . . .
C2 C 0.96668(13) 0.5284(3) 0.10031(6) 0.0489(4) Uani 1 1 d . . .
C3 C 1.08576(13) 0.5042(3) 0.13511(6) 0.0510(4) Uani 1 1 d . . .
C4 C 1.14475(16) 0.3403(3) 0.11379(7) 0.0603(5) Uani 1 1 d . . .
C5 C 1.25623(19) 0.2750(4) 0.13633(10) 0.0790(6) Uani 1 1 d . . .
H5 H 1.2937 0.1627 0.1212 0.095 Uiso 1 1 calc R . .
C6 C 1.31031(18) 0.3825(4) 0.18236(10) 0.0823(7) Uani 1 1 d . . .
H6 H 1.3859 0.3422 0.1989 0.099 Uiso 1 1 calc R . .
C7 C 1.25452(16) 0.5485(4) 0.20430(9) 0.0740(6) Uani 1 1 d . . .
H7 H 1.2929 0.6192 0.2354 0.089 Uiso 1 1 calc R . .
C8 C 1.14197(15) 0.6124(3) 0.18084(7) 0.0610(5) Uani 1 1 d . . .
H8 H 1.1050 0.7264 0.1957 0.073 Uiso 1 1 calc R . .
C9 C 0.93210(15) 0.7658(3) 0.07864(7) 0.0560(5) Uani 1 1 d . . .
H9A H 0.9660 0.8802 0.1042 0.067 Uiso 1 1 calc R . .
H9B H 0.9570 0.7920 0.0455 0.067 Uiso 1 1 calc R . .
C10 C 0.80259(16) 0.7662(3) 0.06994(7) 0.0606(5) Uani 1 1 d . . .
H10 H 0.7550 0.8744 0.0501 0.073 Uiso 1 1 calc R . .
C11 C 0.76319(14) 0.5941(3) 0.09384(6) 0.0556(5) Uani 1 1 d . . .
C12 C 0.85949(12) 0.4478(3) 0.12416(5) 0.0473(4) Uani 1 1 d . . .
H12 H 0.8423 0.2898 0.1148 0.057 Uiso 1 1 calc R . .
C13 C 0.87844(11) 0.4766(3) 0.18393(6) 0.0445(4) Uani 1 1 d . . .
C14 C 0.93409(13) 0.3108(3) 0.21766(6) 0.0500(4) Uani 1 1 d . . .
C15 C 0.95316(15) 0.3232(3) 0.27237(7) 0.0594(5) Uani 1 1 d . . .
H15 H 0.9904 0.2069 0.2936 0.071 Uiso 1 1 calc R . .
C16 C 0.91573(14) 0.5117(4) 0.29481(6) 0.0602(5) Uani 1 1 d . . .
H16 H 0.9276 0.5237 0.3317 0.072 Uiso 1 1 calc R . .
C17 C 0.86101(14) 0.6819(3) 0.26301(7) 0.0588(5) Uani 1 1 d . . .
H17 H 0.8362 0.8096 0.2783 0.071 Uiso 1 1 calc R . .
C18 C 0.84251(13) 0.6639(3) 0.20789(6) 0.0517(4) Uani 1 1 d . . .
H18 H 0.8052 0.7803 0.1867 0.062 Uiso 1 1 calc R . .
C19 C 0.64045(15) 0.5392(4) 0.09326(7) 0.0679(6) Uani 1 1 d . . .
C20 C 0.44425(19) 0.6526(6) 0.06348(13) 0.1058(10) Uani 1 1 d . . .
H20A H 0.4277 0.6402 0.0988 0.127 Uiso 1 1 calc R . .
H20B H 0.4206 0.5140 0.0443 0.127 Uiso 1 1 calc R . .
C21 C 0.3821(3) 0.8433(8) 0.03512(18) 0.1317(13) Uani 1 1 d . . .
H21A H 0.4095 0.9801 0.0535 0.158 Uiso 1 1 calc R . .
H21B H 0.3002 0.8270 0.0336 0.158 Uiso 1 1 calc R . .
H21C H 0.3956 0.8485 -0.0004 0.158 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 0.0890(8) 0.0538(7) 0.0649(6) 0.0010(4) 0.0218(5) 0.0165(5)
O1 0.0846(9) 0.0902(11) 0.0598(8) -0.0222(7) 0.0230(7) -0.0221(7)
O2 0.0801(9) 0.0613(8) 0.0709(8) -0.0140(6) 0.0337(6) 0.0016(6)
O3 0.0620(8) 0.1315(16) 0.1050(12) 0.0552(11) 0.0075(8) -0.0185(9)
O4 0.0516(7) 0.1116(13) 0.0980(11) 0.0307(9) 0.0076(7) 0.0075(7)
C1 0.0708(10) 0.0575(11) 0.0517(9) -0.0063(7) 0.0272(8) -0.0146(8)
C2 0.0527(8) 0.0509(10) 0.0468(8) -0.0029(6) 0.0186(6) -0.0056(6)
C3 0.0498(8) 0.0510(10) 0.0569(9) -0.0013(7) 0.0220(7) -0.0041(6)
C4 0.0655(10) 0.0560(11) 0.0664(10) -0.0039(8) 0.0298(8) -0.0008(7)
C5 0.0687(11) 0.0763(15) 0.0997(16) -0.0019(11) 0.0356(11) 0.0162(10)
C6 0.0545(10) 0.0918(17) 0.1005(16) 0.0075(13) 0.0162(10) 0.0097(10)
C7 0.0534(9) 0.0895(15) 0.0770(12) -0.0012(10) 0.0094(8) -0.0036(9)
C8 0.0518(9) 0.0655(12) 0.0672(10) -0.0099(8) 0.0161(7) -0.0031(7)
C9 0.0646(10) 0.0514(10) 0.0553(9) 0.0026(7) 0.0205(7) -0.0069(7)
C10 0.0639(10) 0.0639(11) 0.0530(9) 0.0107(7) 0.0103(7) 0.0031(8)
C11 0.0515(8) 0.0687(11) 0.0463(8) 0.0066(7) 0.0097(6) -0.0004(7)
C12 0.0494(7) 0.0505(9) 0.0435(7) -0.0001(6) 0.0136(6) -0.0048(6)
C13 0.0405(7) 0.0500(9) 0.0450(7) 0.0003(6) 0.0139(5) -0.0025(5)
C14 0.0500(8) 0.0518(9) 0.0509(8) 0.0001(6) 0.0169(6) 0.0020(6)
C15 0.0570(9) 0.0705(12) 0.0500(9) 0.0087(7) 0.0103(7) 0.0043(8)
C16 0.0549(9) 0.0826(13) 0.0448(8) -0.0057(8) 0.0142(7) -0.0062(8)
C17 0.0523(8) 0.0683(11) 0.0598(10) -0.0141(8) 0.0210(7) -0.0003(7)
C18 0.0465(8) 0.0553(10) 0.0556(9) 0.0000(7) 0.0159(6) 0.0032(6)
C19 0.0544(9) 0.0922(15) 0.0551(9) 0.0149(9) 0.0077(7) -0.0029(9)
C20 0.0512(11) 0.152(3) 0.1095(19) 0.0290(18) 0.0072(11) -0.0005(13)
C21 0.0656(14) 0.157(3) 0.163(3) 0.013(3) 0.0026(17) 0.0194(17)
_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 C14 1.358(2) . ?
O1 C1 1.192(2) . ?
O2 C1 1.366(2) . ?
O2 C4 1.397(2) . ?
O3 C19 1.184(3) . ?
O4 C19 1.330(3) . ?
O4 C20 1.453(3) . ?
C1 C2 1.525(2) . ?
C2 C3 1.498(2) . ?
C2 C9 1.539(3) . ?
C2 C12 1.589(2) . ?
C3 C4 1.376(2) . ?
C3 C8 1.378(2) . ?
C4 C5 1.371(3) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.491(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.327(3) . ?
C10 H10 0.9300 . ?
C11 C19 1.477(2) . ?
C11 C12 1.505(2) . ?
C12 C13 1.514(2) . ?
C12 H12 0.9800 . ?
C13 C14 1.381(2) . ?
C13 C18 1.382(2) . ?
C14 C15 1.378(2) . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 C21 1.457(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C4 107.87(13) . . ?
C19 O4 C20 116.47(19) . . ?
O1 C1 O2 120.43(16) . . ?
O1 C1 C2 129.06(18) . . ?
O2 C1 C2 110.49(14) . . ?
C3 C2 C1 100.97(13) . . ?
C3 C2 C9 116.39(14) . . ?
C1 C2 C9 111.42(13) . . ?
C3 C2 C12 117.25(13) . . ?
C1 C2 C12 106.26(13) . . ?
C9 C2 C12 104.24(13) . . ?
C4 C3 C8 118.66(16) . . ?
C4 C3 C2 108.45(15) . . ?
C8 C3 C2 132.88(15) . . ?
C5 C4 C3 123.39(19) . . ?
C5 C4 O2 124.60(18) . . ?
C3 C4 O2 112.01(16) . . ?
C4 C5 C6 117.11(19) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C7 C6 C5 120.98(19) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 118.83(18) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C2 103.74(13) . . ?
C10 C9 H9A 111.0 . . ?
C2 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C2 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C9 112.11(15) . . ?
C11 C10 H10 123.9 . . ?
C9 C10 H10 123.9 . . ?
C10 C11 C19 127.11(16) . . ?
C10 C11 C12 112.72(15) . . ?
C19 C11 C12 120.17(15) . . ?
C11 C12 C13 112.99(13) . . ?
C11 C12 C2 101.37(12) . . ?
C13 C12 C2 113.65(12) . . ?
C11 C12 H12 109.5 . . ?
C13 C12 H12 109.5 . . ?
C2 C12 H12 109.5 . . ?
C14 C13 C18 116.36(14) . . ?
C14 C13 C12 120.22(14) . . ?
C18 C13 C12 123.42(14) . . ?
F1 C14 C15 118.22(15) . . ?
F1 C14 C13 118.12(14) . . ?
C15 C14 C13 123.66(16) . . ?
C16 C15 C14 118.36(16) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C17 C16 C15 120.18(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.09(16) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 121.35(16) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
O3 C19 O4 123.72(17) . . ?
O3 C19 C11 124.23(18) . . ?
O4 C19 C11 112.05(17) . . ?
O4 C20 C21 107.0(3) . . ?
O4 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O4 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 O2 C1 O1 177.84(16) . . . . ?
C4 O2 C1 C2 -3.97(19) . . . . ?
O1 C1 C2 C3 -177.32(18) . . . . ?
O2 C1 C2 C3 4.69(17) . . . . ?
O1 C1 C2 C9 -53.1(2) . . . . ?
O2 C1 C2 C9 128.92(15) . . . . ?
O1 C1 C2 C12 59.8(2) . . . . ?
O2 C1 C2 C12 -118.15(14) . . . . ?
C1 C2 C3 C4 -3.68(17) . . . . ?
C9 C2 C3 C4 -124.44(16) . . . . ?
C12 C2 C3 C4 111.19(16) . . . . ?
C1 C2 C3 C8 175.33(19) . . . . ?
C9 C2 C3 C8 54.6(2) . . . . ?
C12 C2 C3 C8 -69.8(3) . . . . ?
C8 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 C5 -179.34(19) . . . . ?
C8 C3 C4 O2 -177.52(16) . . . . ?
C2 C3 C4 O2 1.7(2) . . . . ?
C1 O2 C4 C5 -177.52(19) . . . . ?
C1 O2 C4 C3 1.5(2) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
O2 C4 C5 C6 178.32(19) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C4 C3 C8 C7 -1.6(3) . . . . ?
C2 C3 C8 C7 179.51(18) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
C3 C2 C9 C10 -153.37(14) . . . . ?
C1 C2 C9 C10 91.61(15) . . . . ?
C12 C2 C9 C10 -22.58(16) . . . . ?
C2 C9 C10 C11 14.3(2) . . . . ?
C9 C10 C11 C19 -179.11(17) . . . . ?
C9 C10 C11 C12 1.2(2) . . . . ?
C10 C11 C12 C13 106.57(17) . . . . ?
C19 C11 C12 C13 -73.2(2) . . . . ?
C10 C11 C12 C2 -15.43(18) . . . . ?
C19 C11 C12 C2 164.83(16) . . . . ?
C3 C2 C12 C11 153.07(14) . . . . ?
C1 C2 C12 C11 -95.02(15) . . . . ?
C9 C2 C12 C11 22.79(15) . . . . ?
C3 C2 C12 C13 31.5(2) . . . . ?
C1 C2 C12 C13 143.45(14) . . . . ?
C9 C2 C12 C13 -98.75(15) . . . . ?
C11 C12 C13 C14 159.02(14) . . . . ?
C2 C12 C13 C14 -86.16(18) . . . . ?
C11 C12 C13 C18 -20.9(2) . . . . ?
C2 C12 C13 C18 93.90(17) . . . . ?
C18 C13 C14 F1 -178.73(13) . . . . ?
C12 C13 C14 F1 1.3(2) . . . . ?
C18 C13 C14 C15 0.9(2) . . . . ?
C12 C13 C14 C15 -179.09(14) . . . . ?
F1 C14 C15 C16 179.00(15) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C14 C13 C18 C17 -0.5(2) . . . . ?
C12 C13 C18 C17 179.45(14) . . . . ?
C16 C17 C18 C13 -0.1(2) . . . . ?
C20 O4 C19 O3 -1.5(4) . . . . ?
C20 O4 C19 C11 178.9(2) . . . . ?
C10 C11 C19 O3 177.0(2) . . . . ?
C12 C11 C19 O3 -3.3(3) . . . . ?
C10 C11 C19 O4 -3.4(3) . . . . ?
C12 C11 C19 O4 176.32(16) . . . . ?
C19 O4 C20 C21 178.4(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        69.95
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.118