# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
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data_z
_database_code_depnum_ccdc_archive 'CCDC 890419'
#TrackingRef 'Z.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 Cl O4'
_chemical_formula_weight         286.74

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.4900(3)
_cell_length_b                   14.2863(4)
_cell_length_c                   20.8403(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8110(10)
_cell_angle_gamma                90.00
_cell_volume                     3077.52(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8961
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35326
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5410
_reflns_number_gt                3814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of 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^)+(0.1052P)^2^+3.2339P] 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         5410
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2146
_refine_ls_wR_factor_gt          0.1889
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
Cl1 Cl -0.18301(11) 0.86675(9) 0.09079(6) 0.0829(4) Uani 1 1 d . . .
Cl2 Cl 0.69503(10) 0.17808(9) 0.14228(8) 0.0956(5) Uani 1 1 d . . .
O5 O 0.6448(3) 0.3550(2) 0.25227(14) 0.0754(9) Uani 1 1 d . . .
O6 O 0.4547(2) 0.28230(18) 0.23471(11) 0.0548(6) Uani 1 1 d . . .
O7 O 0.4101(2) 0.50010(17) 0.17683(13) 0.0600(7) Uani 1 1 d . . .
H7A H 0.3440 0.5318 0.1715 0.072 Uiso 1 1 calc R . .
O8 O 0.2832(2) 0.40099(16) 0.11378(12) 0.0493(6) Uani 1 1 d . . .
C15 C 0.5108(3) 0.3632(2) 0.14571(15) 0.0377(7) Uani 1 1 d . . .
C16 C 0.6187(3) 0.4219(3) 0.12294(17) 0.0465(8) Uani 1 1 d . . .
H16A H 0.6008 0.4883 0.1254 0.056 Uiso 1 1 calc R . .
H16B H 0.7021 0.4087 0.1494 0.056 Uiso 1 1 calc R . .
C17 C 0.6165(3) 0.3924(3) 0.05416(17) 0.0492(9) Uani 1 1 d . . .
C18 C 0.5437(4) 0.3172(3) 0.03878(16) 0.0495(9) Uani 1 1 d . . .
C19 C 0.4829(3) 0.2822(2) 0.09477(15) 0.0399(7) Uani 1 1 d . . .
H19A H 0.3892 0.2795 0.0800 0.048 Uiso 1 1 calc R . .
C20 C 0.5275(3) 0.1855(2) 0.11635(18) 0.0474(8) Uani 1 1 d . . .
C21 C 0.4566(4) 0.1094(3) 0.1158(2) 0.0601(10) Uani 1 1 d . . .
C22 C 0.5107(6) 0.0139(3) 0.1347(3) 0.0997(18) Uani 1 1 d . . .
H22A H 0.6030 0.0179 0.1469 0.150 Uiso 1 1 calc R . .
H22B H 0.4895 -0.0281 0.0985 0.150 Uiso 1 1 calc R . .
H22C H 0.4742 -0.0092 0.1709 0.150 Uiso 1 1 calc R . .
C23 C 0.3127(5) 0.1120(4) 0.0948(4) 0.106(2) Uani 1 1 d . . .
H23A H 0.2860 0.1748 0.0830 0.159 Uiso 1 1 calc R . .
H23B H 0.2713 0.0913 0.1300 0.159 Uiso 1 1 calc R . .
H23C H 0.2886 0.0714 0.0580 0.159 Uiso 1 1 calc R . .
C24 C 0.3891(3) 0.4228(2) 0.14320(15) 0.0381(7) Uani 1 1 d . . .
C25 C 0.5479(3) 0.3329(2) 0.21654(16) 0.0433(8) Uani 1 1 d . . .
C26 C 0.4791(5) 0.2472(4) 0.3009(2) 0.0783(13) Uani 1 1 d . . .
H26A H 0.4059 0.2116 0.3090 0.118 Uiso 1 1 calc R . .
H26B H 0.4932 0.2989 0.3308 0.118 Uiso 1 1 calc R . .
H26C H 0.5544 0.2079 0.3069 0.118 Uiso 1 1 calc R . .
C27 C 0.5203(5) 0.2647(4) -0.0246(2) 0.0839(14) Uani 1 1 d . . .
H27A H 0.5658 0.2948 -0.0551 0.126 Uiso 1 1 calc R . .
H27B H 0.4294 0.2641 -0.0417 0.126 Uiso 1 1 calc R . .
H27C H 0.5508 0.2016 -0.0175 0.126 Uiso 1 1 calc R . .
C28 C 0.6935(5) 0.4457(3) 0.0123(2) 0.0775(13) Uani 1 1 d . . .
H28A H 0.6824 0.4178 -0.0302 0.116 Uiso 1 1 calc R . .
H28B H 0.7834 0.4441 0.0316 0.116 Uiso 1 1 calc R . .
H28C H 0.6643 0.5095 0.0086 0.116 Uiso 1 1 calc R . .
O1 O -0.0612(3) 0.6045(2) 0.20801(14) 0.0763(9) Uani 1 1 d . . .
O2 O -0.2297(3) 0.6347(2) 0.13119(16) 0.0778(9) Uani 1 1 d . . .
O3 O 0.0719(2) 0.50742(16) 0.10166(13) 0.0556(7) Uani 1 1 d . . .
H3B H 0.1375 0.4752 0.1065 0.067 Uiso 1 1 calc R . .
O4 O 0.2065(2) 0.61234(18) 0.15402(13) 0.0573(7) Uani 1 1 d . . .
C1 C 0.0191(4) 0.7361(3) 0.01349(19) 0.0646(11) Uani 1 1 d . . .
C2 C 0.0710(4) 0.7927(3) 0.0622(2) 0.0624(10) Uani 1 1 d . . .
C3 C 0.0363(3) 0.7609(2) 0.12700(19) 0.0522(9) Uani 1 1 d . . .
H3A H 0.1151 0.7584 0.1598 0.063 Uiso 1 1 calc R . .
C4 C -0.0135(3) 0.6588(2) 0.11048(16) 0.0411(7) Uani 1 1 d . . .
C5 C -0.0613(3) 0.6626(3) 0.03644(17) 0.0501(9) Uani 1 1 d . . .
H5A H -0.0486 0.6029 0.0163 0.060 Uiso 1 1 calc R . .
H5B H -0.1523 0.6790 0.0268 0.060 Uiso 1 1 calc R . .
C6 C -0.0589(3) 0.8255(3) 0.14991(19) 0.0516(9) Uani 1 1 d . . .
C7 C -0.0604(4) 0.8516(3) 0.2121(2) 0.0614(10) Uani 1 1 d . . .
C8 C 0.0376(5) 0.8164(4) 0.2677(2) 0.0836(14) Uani 1 1 d . . .
H8A H 0.0995 0.7777 0.2513 0.125 Uiso 1 1 calc R . .
H8B H -0.0052 0.7805 0.2967 0.125 Uiso 1 1 calc R . .
H8C H 0.0812 0.8686 0.2908 0.125 Uiso 1 1 calc R . .
C9 C -0.1608(5) 0.9144(4) 0.2318(3) 0.0958(18) Uani 1 1 d . . .
H9A H -0.2195 0.9343 0.1938 0.144 Uiso 1 1 calc R . .
H9B H -0.1198 0.9681 0.2540 0.144 Uiso 1 1 calc R . .
H9C H -0.2078 0.8811 0.2603 0.144 Uiso 1 1 calc R . .
C10 C 0.0244(5) 0.7462(4) -0.0569(2) 0.0878(15) Uani 1 1 d . . .
H10A H 0.0808 0.7972 -0.0630 0.132 Uiso 1 1 calc R . .
H10B H -0.0609 0.7587 -0.0804 0.132 Uiso 1 1 calc R . .
H10C H 0.0566 0.6894 -0.0728 0.132 Uiso 1 1 calc R . .
C11 C -0.1164(3) 0.6291(3) 0.14920(18) 0.0490(9) Uani 1 1 d . . .
C12 C -0.1473(6) 0.5835(5) 0.2550(3) 0.0992(18) Uani 1 1 d . . .
H12A H -0.0963 0.5668 0.2961 0.149 Uiso 1 1 calc R . .
H12B H -0.2030 0.5322 0.2391 0.149 Uiso 1 1 calc R . .
H12C H -0.1987 0.6376 0.2604 0.149 Uiso 1 1 calc R . .
C13 C 0.1005(3) 0.5913(2) 0.12487(16) 0.0407(7) Uani 1 1 d . . .
C14 C 0.1532(6) 0.8782(4) 0.0626(3) 0.0978(18) Uani 1 1 d . . .
H14A H 0.1674 0.8911 0.0191 0.147 Uiso 1 1 calc R . .
H14B H 0.2349 0.8680 0.0904 0.147 Uiso 1 1 calc R . .
H14C H 0.1103 0.9305 0.0785 0.147 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 0.0698(7) 0.0846(8) 0.0866(8) -0.0110(6) -0.0089(6) 0.0340(6)
Cl2 0.0453(6) 0.0660(7) 0.1646(14) 0.0098(8) -0.0137(7) 0.0115(5)
O5 0.0534(17) 0.112(3) 0.0554(16) 0.0129(16) -0.0064(13) -0.0100(16)
O6 0.0568(15) 0.0610(16) 0.0463(14) 0.0134(12) 0.0075(11) -0.0077(12)
O7 0.0502(14) 0.0507(15) 0.0736(17) -0.0223(13) -0.0055(12) 0.0097(12)
O8 0.0372(13) 0.0455(14) 0.0627(15) -0.0058(11) 0.0014(11) 0.0049(10)
C15 0.0363(16) 0.0371(17) 0.0396(17) 0.0013(13) 0.0057(13) -0.0010(13)
C16 0.0412(18) 0.0455(19) 0.054(2) 0.0019(16) 0.0107(15) -0.0058(15)
C17 0.049(2) 0.053(2) 0.0478(19) 0.0096(16) 0.0165(16) 0.0044(17)
C18 0.056(2) 0.054(2) 0.0399(18) -0.0007(16) 0.0117(16) 0.0039(17)
C19 0.0348(16) 0.0376(17) 0.0458(18) -0.0019(14) 0.0032(13) 0.0010(13)
C20 0.0429(18) 0.0392(19) 0.059(2) -0.0012(16) 0.0046(15) 0.0031(15)
C21 0.062(2) 0.044(2) 0.074(3) 0.0027(18) 0.011(2) -0.0020(18)
C22 0.118(4) 0.043(3) 0.133(5) 0.012(3) 0.009(4) 0.002(3)
C23 0.066(3) 0.075(3) 0.173(6) 0.011(4) 0.009(3) -0.026(3)
C24 0.0395(18) 0.0385(17) 0.0363(16) 0.0028(13) 0.0063(13) 0.0005(14)
C25 0.0383(18) 0.0468(19) 0.0440(18) 0.0033(15) 0.0041(15) 0.0058(15)
C26 0.098(3) 0.083(3) 0.055(2) 0.026(2) 0.015(2) 0.000(3)
C27 0.108(4) 0.092(4) 0.054(3) -0.020(2) 0.021(2) -0.007(3)
C28 0.086(3) 0.080(3) 0.074(3) 0.019(2) 0.039(2) -0.001(3)
O1 0.0717(19) 0.099(2) 0.0620(18) 0.0130(16) 0.0216(15) -0.0036(17)
O2 0.0534(18) 0.093(2) 0.089(2) 0.0060(17) 0.0172(16) -0.0054(16)
O3 0.0458(14) 0.0398(14) 0.0791(18) -0.0116(12) 0.0042(12) 0.0055(11)
O4 0.0432(14) 0.0504(15) 0.0738(17) -0.0156(12) -0.0028(12) 0.0098(11)
C1 0.059(2) 0.086(3) 0.052(2) -0.006(2) 0.0193(19) -0.005(2)
C2 0.062(2) 0.059(2) 0.070(3) -0.001(2) 0.024(2) -0.002(2)
C3 0.0411(19) 0.047(2) 0.068(2) -0.0138(17) 0.0058(17) 0.0035(15)
C4 0.0382(17) 0.0387(18) 0.0464(18) -0.0045(14) 0.0075(14) 0.0037(13)
C5 0.052(2) 0.049(2) 0.048(2) -0.0042(16) 0.0067(16) 0.0047(16)
C6 0.0422(19) 0.046(2) 0.062(2) -0.0104(17) -0.0038(16) 0.0043(15)
C7 0.053(2) 0.067(3) 0.063(2) -0.020(2) 0.0053(18) -0.0020(19)
C8 0.077(3) 0.112(4) 0.058(3) -0.022(3) -0.001(2) 0.001(3)
C9 0.077(3) 0.115(4) 0.098(4) -0.048(3) 0.019(3) 0.013(3)
C10 0.086(3) 0.124(4) 0.058(3) 0.002(3) 0.023(2) 0.013(3)
C11 0.043(2) 0.050(2) 0.055(2) -0.0052(16) 0.0116(16) 0.0040(16)
C12 0.106(4) 0.123(5) 0.078(3) 0.022(3) 0.042(3) -0.009(3)
C13 0.0404(18) 0.0414(19) 0.0418(17) -0.0052(14) 0.0108(14) 0.0032(14)
C14 0.107(4) 0.072(3) 0.125(5) -0.005(3) 0.050(4) -0.029(3)

_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 C6 1.736(4) . ?
Cl2 C20 1.751(4) . ?
O5 C25 1.195(4) . ?
O6 C25 1.322(4) . ?
O6 C26 1.450(5) . ?
O7 C24 1.306(4) . ?
O7 H7A 0.8200 . ?
O8 C24 1.214(4) . ?
C15 C25 1.524(4) . ?
C15 C24 1.529(4) . ?
C15 C16 1.547(4) . ?
C15 C19 1.564(4) . ?
C16 C17 1.491(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.325(5) . ?
C17 C28 1.494(5) . ?
C18 C27 1.502(5) . ?
C18 C19 1.507(5) . ?
C19 C20 1.503(5) . ?
C19 H19A 0.9800 . ?
C20 C21 1.317(5) . ?
C21 C23 1.499(6) . ?
C21 C22 1.504(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
O1 C11 1.311(5) . ?
O1 C12 1.471(5) . ?
O2 C11 1.186(4) . ?
O3 C13 1.308(4) . ?
O3 H3B 0.8200 . ?
O4 C13 1.210(4) . ?
C1 C2 1.339(6) . ?
C1 C5 1.476(6) . ?
C1 C10 1.485(6) . ?
C2 C14 1.496(6) . ?
C2 C3 1.525(6) . ?
C3 C6 1.496(5) . ?
C3 C4 1.568(5) . ?
C3 H3A 0.9800 . ?
C4 C11 1.515(5) . ?
C4 C13 1.526(4) . ?
C4 C5 1.540(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.351(5) . ?
C7 C9 1.494(6) . ?
C7 C8 1.499(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C25 O6 C26 116.3(3) . . ?
C24 O7 H7A 109.5 . . ?
C25 C15 C24 105.4(2) . . ?
C25 C15 C16 111.8(3) . . ?
C24 C15 C16 109.7(3) . . ?
C25 C15 C19 115.8(3) . . ?
C24 C15 C19 109.3(2) . . ?
C16 C15 C19 104.8(2) . . ?
C17 C16 C15 104.4(3) . . ?
C17 C16 H16A 110.9 . . ?
C15 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C18 C17 C16 112.0(3) . . ?
C18 C17 C28 128.2(4) . . ?
C16 C17 C28 119.7(4) . . ?
C17 C18 C27 128.2(4) . . ?
C17 C18 C19 112.6(3) . . ?
C27 C18 C19 119.1(3) . . ?
C20 C19 C18 112.7(3) . . ?
C20 C19 C15 117.7(3) . . ?
C18 C19 C15 103.0(3) . . ?
C20 C19 H19A 107.7 . . ?
C18 C19 H19A 107.7 . . ?
C15 C19 H19A 107.7 . . ?
C21 C20 C19 127.6(3) . . ?
C21 C20 Cl2 119.3(3) . . ?
C19 C20 Cl2 113.1(2) . . ?
C20 C21 C23 121.4(4) . . ?
C20 C21 C22 124.0(4) . . ?
C23 C21 C22 114.5(4) . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 C24 O7 123.0(3) . . ?
O8 C24 C15 124.1(3) . . ?
O7 C24 C15 112.9(3) . . ?
O5 C25 O6 123.9(3) . . ?
O5 C25 C15 125.4(3) . . ?
O6 C25 C15 110.7(3) . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O6 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 C27 H27A 109.5 . . ?
C18 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C18 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C28 H28A 109.5 . . ?
C17 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C17 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C11 O1 C12 117.0(4) . . ?
C13 O3 H3B 109.5 . . ?
C2 C1 C5 111.4(3) . . ?
C2 C1 C10 127.7(4) . . ?
C5 C1 C10 120.6(4) . . ?
C1 C2 C14 131.0(4) . . ?
C1 C2 C3 111.4(3) . . ?
C14 C2 C3 117.6(4) . . ?
C6 C3 C2 111.8(3) . . ?
C6 C3 C4 115.4(3) . . ?
C2 C3 C4 101.7(3) . . ?
C6 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C11 C4 C13 109.0(3) . . ?
C11 C4 C5 113.8(3) . . ?
C13 C4 C5 109.3(3) . . ?
C11 C4 C3 112.6(3) . . ?
C13 C4 C3 108.9(3) . . ?
C5 C4 C3 103.1(3) . . ?
C1 C5 C4 104.1(3) . . ?
C1 C5 H5A 110.9 . . ?
C4 C5 H5A 110.9 . . ?
C1 C5 H5B 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 109.0 . . ?
C7 C6 C3 126.4(3) . . ?
C7 C6 Cl1 117.2(3) . . ?
C3 C6 Cl1 116.3(3) . . ?
C6 C7 C9 123.6(4) . . ?
C6 C7 C8 122.1(4) . . ?
C9 C7 C8 114.3(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O1 125.0(4) . . ?
O2 C11 C4 125.4(4) . . ?
O1 C11 C4 109.4(3) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 O3 123.1(3) . . ?
O4 C13 C4 124.3(3) . . ?
O3 C13 C4 112.5(3) . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C25 C15 C16 C17 143.0(3) . . . . ?
C24 C15 C16 C17 -100.4(3) . . . . ?
C19 C15 C16 C17 16.8(3) . . . . ?
C15 C16 C17 C18 -11.1(4) . . . . ?
C15 C16 C17 C28 170.0(3) . . . . ?
C16 C17 C18 C27 -177.9(4) . . . . ?
C28 C17 C18 C27 0.8(7) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C28 C17 C18 C19 178.8(4) . . . . ?
C17 C18 C19 C20 -117.0(3) . . . . ?
C27 C18 C19 C20 61.2(5) . . . . ?
C17 C18 C19 C15 10.8(4) . . . . ?
C27 C18 C19 C15 -171.0(4) . . . . ?
C25 C15 C19 C20 -15.6(4) . . . . ?
C24 C15 C19 C20 -134.4(3) . . . . ?
C16 C15 C19 C20 108.1(3) . . . . ?
C25 C15 C19 C18 -140.2(3) . . . . ?
C24 C15 C19 C18 101.0(3) . . . . ?
C16 C15 C19 C18 -16.6(3) . . . . ?
C18 C19 C20 C21 -118.2(4) . . . . ?
C15 C19 C20 C21 122.2(4) . . . . ?
C18 C19 C20 Cl2 59.8(4) . . . . ?
C15 C19 C20 Cl2 -59.9(4) . . . . ?
C19 C20 C21 C23 -2.9(7) . . . . ?
Cl2 C20 C21 C23 179.3(4) . . . . ?
C19 C20 C21 C22 176.3(4) . . . . ?
Cl2 C20 C21 C22 -1.6(6) . . . . ?
C25 C15 C24 O8 -114.3(3) . . . . ?
C16 C15 C24 O8 125.2(3) . . . . ?
C19 C15 C24 O8 10.8(4) . . . . ?
C25 C15 C24 O7 65.0(3) . . . . ?
C16 C15 C24 O7 -55.5(3) . . . . ?
C19 C15 C24 O7 -169.9(3) . . . . ?
C26 O6 C25 O5 -4.6(5) . . . . ?
C26 O6 C25 C15 178.7(3) . . . . ?
C24 C15 C25 O5 -115.4(4) . . . . ?
C16 C15 C25 O5 3.8(5) . . . . ?
C19 C15 C25 O5 123.7(4) . . . . ?
C24 C15 C25 O6 61.3(3) . . . . ?
C16 C15 C25 O6 -179.6(3) . . . . ?
C19 C15 C25 O6 -59.6(4) . . . . ?
C5 C1 C2 C14 -177.0(5) . . . . ?
C10 C1 C2 C14 -3.4(8) . . . . ?
C5 C1 C2 C3 2.7(5) . . . . ?
C10 C1 C2 C3 176.3(4) . . . . ?
C1 C2 C3 C6 -108.3(4) . . . . ?
C14 C2 C3 C6 71.4(5) . . . . ?
C1 C2 C3 C4 15.3(4) . . . . ?
C14 C2 C3 C4 -164.9(4) . . . . ?
C6 C3 C4 C11 -27.9(4) . . . . ?
C2 C3 C4 C11 -149.1(3) . . . . ?
C6 C3 C4 C13 -148.8(3) . . . . ?
C2 C3 C4 C13 89.9(3) . . . . ?
C6 C3 C4 C5 95.2(4) . . . . ?
C2 C3 C4 C5 -26.0(3) . . . . ?
C2 C1 C5 C4 -20.1(4) . . . . ?
C10 C1 C5 C4 165.8(4) . . . . ?
C11 C4 C5 C1 150.4(3) . . . . ?
C13 C4 C5 C1 -87.5(3) . . . . ?
C3 C4 C5 C1 28.2(3) . . . . ?
C2 C3 C6 C7 -142.1(4) . . . . ?
C4 C3 C6 C7 102.3(5) . . . . ?
C2 C3 C6 Cl1 40.7(4) . . . . ?
C4 C3 C6 Cl1 -74.9(4) . . . . ?
C3 C6 C7 C9 -178.2(4) . . . . ?
Cl1 C6 C7 C9 -1.0(6) . . . . ?
C3 C6 C7 C8 -0.4(7) . . . . ?
Cl1 C6 C7 C8 176.8(4) . . . . ?
C12 O1 C11 O2 -0.7(6) . . . . ?
C12 O1 C11 C4 173.4(4) . . . . ?
C13 C4 C11 O2 -144.3(4) . . . . ?
C5 C4 C11 O2 -22.1(5) . . . . ?
C3 C4 C11 O2 94.8(4) . . . . ?
C13 C4 C11 O1 41.6(4) . . . . ?
C5 C4 C11 O1 163.8(3) . . . . ?
C3 C4 C11 O1 -79.4(4) . . . . ?
C11 C4 C13 O4 -112.3(4) . . . . ?
C5 C4 C13 O4 122.8(4) . . . . ?
C3 C4 C13 O4 10.9(5) . . . . ?
C11 C4 C13 O3 68.3(3) . . . . ?
C5 C4 C13 O3 -56.6(4) . . . . ?
C3 C4 C13 O3 -168.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.985
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.059