# 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.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_110922a_0m
#TrackingRef '110922a_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H25 Br O4'
_chemical_formula_weight         517.40

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           ?
_symmetry_space_group_name_H-M   ?

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                   14.1122(15)
_cell_length_b                   10.9377(11)
_cell_length_c                   16.8822(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.9120(10)
_cell_angle_gamma                90.00
_cell_volume                     2574.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    1.628
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6238
_exptl_absorpt_correction_T_max  0.6496
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21791
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.63
_reflns_number_total             5927
_reflns_number_gt                3341
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0738P)²+0.4211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5927
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001

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 0.69263(2) 0.83797(3) 0.08082(2) 0.08541(18) Uani 1 1 d . . .
C1 C 0.06618(16) 1.1376(2) 0.07149(11) 0.0834(9) Uani 1 1 d G . .
H1 H 0.0781 1.0978 0.0254 0.100 Uiso 1 1 calc R . .
C2 C -0.02233(14) 1.1924(3) 0.07328(15) 0.1067(13) Uani 1 1 d G . .
H2 H -0.0696 1.1893 0.0283 0.128 Uiso 1 1 calc R . .
C3 C -0.04019(13) 1.2518(2) 0.14223(19) 0.1105(14) Uani 1 1 d G . .
H3 H -0.0994 1.2885 0.1434 0.133 Uiso 1 1 calc R . .
C4 C 0.03046(19) 1.2564(2) 0.20940(15) 0.1063(12) Uani 1 1 d G . .
H4 H 0.0185 1.2962 0.2555 0.128 Uiso 1 1 calc R . .
C5 C 0.11896(15) 1.2016(2) 0.20762(11) 0.0839(9) Uani 1 1 d G . .
H5 H 0.1662 1.2047 0.2526 0.101 Uiso 1 1 calc R . .
C6 C 0.13683(12) 1.14220(18) 0.13866(12) 0.0623(7) Uani 1 1 d G . .
C7 C 0.2282(2) 1.0866(3) 0.13627(17) 0.0658(7) Uani 1 1 d . . .
C8 C 0.3057(2) 1.0459(3) 0.13326(17) 0.0664(7) Uani 1 1 d . . .
C9 C 0.39793(19) 0.9973(3) 0.12458(16) 0.0611(7) Uani 1 1 d . . .
C10 C 0.4847(2) 1.0469(3) 0.16545(16) 0.0613(7) Uani 1 1 d . . .
C11 C 0.57106(19) 0.9974(3) 0.15142(16) 0.0628(7) Uani 1 1 d . . .
H11 H 0.6285 1.0308 0.1767 0.075 Uiso 1 1 calc R . .
C12 C 0.57262(18) 0.8991(3) 0.10037(16) 0.0603(7) Uani 1 1 d . . .
C13 C 0.48884(19) 0.8465(2) 0.06232(16) 0.0585(7) Uani 1 1 d . . .
C14 C 0.40282(18) 0.8975(3) 0.07438(16) 0.0606(7) Uani 1 1 d . . .
C15 C 0.48572(16) 1.14990(16) 0.22416(10) 0.0673(8) Uani 1 1 d G . .
C16 C 0.43082(16) 1.25438(19) 0.20516(11) 0.0810(9) Uani 1 1 d G . .
H16 H 0.3930 1.2616 0.1551 0.097 Uiso 1 1 calc R . .
C17 C 0.43241(19) 1.34811(17) 0.26095(15) 0.1027(12) Uani 1 1 d G . .
H17 H 0.3957 1.4180 0.2482 0.123 Uiso 1 1 calc R . .
C18 C 0.4889(2) 1.3374(2) 0.33575(13) 0.1094(14) Uani 1 1 d G . .
H18 H 0.4900 1.4001 0.3731 0.131 Uiso 1 1 calc R . .
C19 C 0.54382(19) 1.2329(2) 0.35475(10) 0.1023(12) Uani 1 1 d G . .
H19 H 0.5816 1.2257 0.4048 0.123 Uiso 1 1 calc R . .
C20 C 0.54223(16) 1.13915(18) 0.29895(12) 0.0831(9) Uani 1 1 d G . .
H20 H 0.5790 1.0693 0.3117 0.100 Uiso 1 1 calc R . .
C21 C 0.3198(2) 0.8324(3) 0.0260(2) 0.0756(8) Uani 1 1 d . . .
H21A H 0.2900 0.8830 -0.0182 0.091 Uiso 1 1 calc R . .
H21B H 0.2719 0.8107 0.0591 0.091 Uiso 1 1 calc R . .
C22 C 0.3646(2) 0.7170(3) -0.00534(17) 0.0675(7) Uani 1 1 d . . .
C23 C 0.4743(2) 0.7385(3) 0.00729(17) 0.0706(8) Uani 1 1 d . . .
H23A H 0.5084 0.6676 0.0316 0.085 Uiso 1 1 calc R . .
H23B H 0.4962 0.7561 -0.0432 0.085 Uiso 1 1 calc R . .
C24 C 0.3273(2) 0.6964(3) -0.0934(2) 0.0728(8) Uani 1 1 d . A .
C25 C 0.3228(8) 0.5750(14) -0.2036(9) 0.078(3) Uani 0.584(18) 1 d P A 1
H25A H 0.3479 0.6394 -0.2340 0.094 Uiso 0.584(18) 1 calc PR A 1
H25B H 0.2534 0.5757 -0.2154 0.094 Uiso 0.584(18) 1 calc PR A 1
C26 C 0.3626(15) 0.4507(16) -0.2230(11) 0.111(4) Uani 0.584(18) 1 d P A 1
H26A H 0.4313 0.4519 -0.2105 0.166 Uiso 0.584(18) 1 calc PR A 1
H26B H 0.3439 0.4333 -0.2790 0.166 Uiso 0.584(18) 1 calc PR A 1
H26C H 0.3377 0.3886 -0.1917 0.166 Uiso 0.584(18) 1 calc PR A 1
C25' C 0.342(3) 0.538(3) -0.2011(17) 0.161(13) Uani 0.416(18) 1 d P A 2
H25C H 0.2861 0.5755 -0.2320 0.193 Uiso 0.416(18) 1 calc PR A 2
H25D H 0.3972 0.5603 -0.2261 0.193 Uiso 0.416(18) 1 calc PR A 2
C26' C 0.333(3) 0.437(3) -0.204(2) 0.22(2) Uani 0.416(18) 1 d P A 2
H26D H 0.3812 0.3988 -0.1656 0.326 Uiso 0.416(18) 1 calc PR A 2
H26E H 0.3406 0.4092 -0.2572 0.326 Uiso 0.416(18) 1 calc PR A 2
H26F H 0.2707 0.4152 -0.1936 0.326 Uiso 0.416(18) 1 calc PR A 2
C27 C 0.3396(3) 0.6044(3) 0.0421(2) 0.0826(9) Uani 1 1 d . A .
C28 C 0.210(2) 0.470(3) 0.0564(19) 0.149(12) Uani 0.584(18) 1 d P A 1
H28A H 0.2620 0.4150 0.0770 0.178 Uiso 0.584(18) 1 calc PR A 1
H28B H 0.1650 0.4282 0.0167 0.178 Uiso 0.584(18) 1 calc PR A 1
C29 C 0.1637(13) 0.5192(12) 0.1210(13) 0.192(8) Uani 0.584(18) 1 d P A 1
H29A H 0.1320 0.5946 0.1039 0.288 Uiso 0.584(18) 1 calc PR A 1
H29B H 0.2110 0.5339 0.1674 0.288 Uiso 0.584(18) 1 calc PR A 1
H29C H 0.1174 0.4613 0.1341 0.288 Uiso 0.584(18) 1 calc PR A 1
C28' C 0.209(3) 0.482(3) 0.071(3) 0.122(11) Uani 0.416(18) 1 d P A 2
H28C H 0.2408 0.4043 0.0648 0.146 Uiso 0.416(18) 1 calc PR A 2
H28D H 0.2187 0.5027 0.1278 0.146 Uiso 0.416(18) 1 calc PR A 2
C29' C 0.1152(14) 0.4754(15) 0.0416(15) 0.168(9) Uani 0.416(18) 1 d P A 2
H29D H 0.0843 0.5501 0.0531 0.252 Uiso 0.416(18) 1 calc PR A 2
H29E H 0.0867 0.4081 0.0658 0.252 Uiso 0.416(18) 1 calc PR A 2
H29F H 0.1075 0.4636 -0.0154 0.252 Uiso 0.416(18) 1 calc PR A 2
O1 O 0.28050(18) 0.7673(2) -0.13665(14) 0.0957(7) Uani 1 1 d . . .
O2 O 0.3559(2) 0.5903(2) -0.11684(13) 0.0991(8) Uani 1 1 d . . .
O3 O 0.3929(2) 0.5515(3) 0.09022(18) 0.1261(11) Uani 1 1 d . . .
O4 O 0.2471(2) 0.5804(3) 0.02309(18) 0.1117(9) Uani 1 1 d . . .


_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 C12 1.897(3) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.433(3) . ?
C7 C8 1.188(4) . ?
C8 C9 1.434(4) . ?
C9 C14 1.391(4) . ?
C9 C10 1.417(4) . ?
C10 C11 1.387(4) . ?
C10 C15 1.499(3) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C13 C14 1.380(4) . ?
C13 C23 1.497(4) . ?
C14 C21 1.501(4) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.542(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C24 1.515(4) . ?
C22 C27 1.540(5) . ?
C22 C23 1.547(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O1 1.192(4) . ?
C24 O2 1.309(4) . ?
C25 O2 1.476(14) . ?
C25 C26 1.526(18) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C25' C26' 1.11(4) . ?
C25' O2 1.52(3) . ?
C25' H25C 0.9700 . ?
C25' H25D 0.9700 . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 0.9600 . ?
C27 O3 1.170(4) . ?
C27 O4 1.321(4) . ?
C28 O4 1.46(3) . ?
C28 C29 1.46(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C28' C29' 1.35(5) . ?
C28' O4 1.50(2) . ?
C28' H28C 0.9700 . ?
C28' H28D 0.9700 . ?
C29' H29D 0.9600 . ?
C29' H29E 0.9600 . ?
C29' H29F 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
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 120.21(18) . . ?
C1 C6 C7 119.78(18) . . ?
C8 C7 C6 176.8(3) . . ?
C7 C8 C9 176.6(3) . . ?
C14 C9 C10 118.5(2) . . ?
C14 C9 C8 119.0(3) . . ?
C10 C9 C8 122.6(3) . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 C15 119.2(2) . . ?
C9 C10 C15 121.9(2) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 Br1 119.0(2) . . ?
C13 C12 Br1 119.7(2) . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 C23 111.8(2) . . ?
C12 C13 C23 130.0(2) . . ?
C13 C14 C9 122.4(3) . . ?
C13 C14 C21 111.0(3) . . ?
C9 C14 C21 126.6(2) . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C10 121.15(16) . . ?
C20 C15 C10 118.85(16) . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C14 C21 C22 104.3(2) . . ?
C14 C21 H21A 110.9 . . ?
C22 C21 H21A 110.9 . . ?
C14 C21 H21B 110.9 . . ?
C22 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
C24 C22 C27 108.6(3) . . ?
C24 C22 C21 111.0(3) . . ?
C27 C22 C21 109.7(3) . . ?
C24 C22 C23 110.3(3) . . ?
C27 C22 C23 110.8(3) . . ?
C21 C22 C23 106.4(2) . . ?
C13 C23 C22 104.1(2) . . ?
C13 C23 H23A 110.9 . . ?
C22 C23 H23A 110.9 . . ?
C13 C23 H23B 110.9 . . ?
C22 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
O1 C24 O2 124.0(3) . . ?
O1 C24 C22 125.4(3) . . ?
O2 C24 C22 110.6(3) . . ?
O2 C25 C26 104.1(11) . . ?
O2 C25 H25A 110.9 . . ?
C26 C25 H25A 110.9 . . ?
O2 C25 H25B 110.9 . . ?
C26 C25 H25B 110.9 . . ?
H25A C25 H25B 108.9 . . ?
C26' C25' O2 115(3) . . ?
C26' C25' H25C 108.6 . . ?
O2 C25' H25C 108.6 . . ?
C26' C25' H25D 108.6 . . ?
O2 C25' H25D 108.6 . . ?
H25C C25' H25D 107.5 . . ?
C25' C26' H26D 109.5 . . ?
C25' C26' H26E 109.5 . . ?
H26D C26' H26E 109.5 . . ?
C25' C26' H26F 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 109.5 . . ?
O3 C27 O4 125.1(4) . . ?
O3 C27 C22 125.6(4) . . ?
O4 C27 C22 109.2(3) . . ?
O4 C28 C29 102(2) . . ?
O4 C28 H28A 111.3 . . ?
C29 C28 H28A 111.3 . . ?
O4 C28 H28B 111.3 . . ?
C29 C28 H28B 111.3 . . ?
H28A C28 H28B 109.2 . . ?
C29' C28' O4 104(3) . . ?
C29' C28' H28C 110.9 . . ?
O4 C28' H28C 110.9 . . ?
C29' C28' H28D 110.9 . . ?
O4 C28' H28D 110.9 . . ?
H28C C28' H28D 108.9 . . ?
C28' C29' H29D 109.5 . . ?
C28' C29' H29E 109.5 . . ?
H29D C29' H29E 109.5 . . ?
C28' C29' H29F 109.5 . . ?
H29D C29' H29F 109.5 . . ?
H29E C29' H29F 109.5 . . ?
C24 O2 C25 109.6(6) . . ?
C24 O2 C25' 128.1(11) . . ?
C25 O2 C25' 18.7(14) . . ?
C27 O4 C28 117.8(13) . . ?
C27 O4 C28' 115.6(17) . . ?
C28 O4 C28' 11(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 901558'
#######################################################################
#
#                 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_111222a
#TrackingRef '111222a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H25 Cl O4'
_chemical_formula_weight         472.94

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                   9.4930(12)
_cell_length_b                   32.264(4)
_cell_length_c                   7.8878(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.902(2)
_cell_angle_gamma                90.00
_cell_volume                     2415.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7275
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.39

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20851
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.64
_reflns_number_total             5582
_reflns_number_gt                4079
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0791P)²+0.5210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5582
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.05989(18) 0.07969(5) 0.4108(2) 0.0437(4) Uani 1 1 d . . .
C2 C 0.0760(2) 0.05272(6) 0.4120(3) 0.0529(5) Uani 1 1 d . . .
H2A H 0.0962 0.0419 0.5245 0.063 Uiso 1 1 calc R . .
H2B H 0.0668 0.0297 0.3333 0.063 Uiso 1 1 calc R . .
C3 C 0.18877(19) 0.08196(5) 0.3577(2) 0.0433(4) Uani 1 1 d . . .
C4 C 0.3275(2) 0.07382(5) 0.3221(3) 0.0465(4) Uani 1 1 d . . .
C5 C 0.41813(19) 0.10477(6) 0.2737(3) 0.0472(4) Uani 1 1 d . . .
H5 H 0.5104 0.0982 0.2466 0.057 Uiso 1 1 calc R . .
C6 C 0.37327(18) 0.14608(5) 0.2647(2) 0.0407(4) Uani 1 1 d . . .
C7 C 0.23193(18) 0.15530(5) 0.3059(2) 0.0387(4) Uani 1 1 d . . .
C8 C 0.14172(18) 0.12271(5) 0.3488(2) 0.0402(4) Uani 1 1 d . . .
C9 C -0.01081(18) 0.12560(5) 0.3952(3) 0.0461(4) Uani 1 1 d . . .
H9A H -0.0647 0.1400 0.3078 0.055 Uiso 1 1 calc R . .
H9B H -0.0215 0.1401 0.5019 0.055 Uiso 1 1 calc R . .
C10 C 0.47577(18) 0.17863(5) 0.2181(2) 0.0405(4) Uani 1 1 d . . .
C11 C 0.61451(19) 0.17695(6) 0.2790(2) 0.0453(4) Uani 1 1 d . . .
H11 H 0.6437 0.1548 0.3462 0.054 Uiso 1 1 calc R . .
C12 C 0.7088(2) 0.20804(6) 0.2403(3) 0.0523(5) Uani 1 1 d . . .
H12 H 0.8009 0.2066 0.2818 0.063 Uiso 1 1 calc R . .
C13 C 0.6680(2) 0.24083(7) 0.1415(3) 0.0599(6) Uani 1 1 d . . .
H13 H 0.7313 0.2621 0.1188 0.072 Uiso 1 1 calc R . .
C14 C 0.5327(2) 0.24232(7) 0.0758(3) 0.0625(6) Uani 1 1 d . . .
H14 H 0.5055 0.2642 0.0059 0.075 Uiso 1 1 calc R . .
C15 C 0.4378(2) 0.21152(6) 0.1131(2) 0.0510(5) Uani 1 1 d . . .
H15 H 0.3470 0.2127 0.0675 0.061 Uiso 1 1 calc R . .
C16 C 0.18116(18) 0.19706(5) 0.3128(2) 0.0410(4) Uani 1 1 d . . .
C17 C 0.14217(19) 0.23220(5) 0.3210(2) 0.0429(4) Uani 1 1 d . . .
C18 C 0.10673(18) 0.27529(5) 0.3314(2) 0.0410(4) Uani 1 1 d . . .
C19 C 0.1987(2) 0.30502(6) 0.2698(3) 0.0545(5) Uani 1 1 d . . .
H19 H 0.2802 0.2970 0.2147 0.065 Uiso 1 1 calc R . .
C20 C 0.1684(3) 0.34665(6) 0.2909(3) 0.0662(6) Uani 1 1 d . . .
H20 H 0.2302 0.3665 0.2502 0.079 Uiso 1 1 calc R . .
C21 C 0.0481(3) 0.35892(6) 0.3714(3) 0.0626(6) Uani 1 1 d . . .
H21 H 0.0294 0.3870 0.3868 0.075 Uiso 1 1 calc R . .
C22 C -0.0440(3) 0.32976(6) 0.4286(3) 0.0610(6) Uani 1 1 d . . .
H22 H -0.1268 0.3380 0.4803 0.073 Uiso 1 1 calc R . .
C23 C -0.0150(2) 0.28828(6) 0.4103(3) 0.0526(5) Uani 1 1 d . . .
H23 H -0.0778 0.2687 0.4514 0.063 Uiso 1 1 calc R . .
C24 C -0.1429(2) 0.07348(5) 0.5724(3) 0.0474(4) Uani 1 1 d . . .
C25 C -0.3453(4) 0.09478(9) 0.7217(4) 0.0901(9) Uani 1 1 d . . .
H25A H -0.4100 0.0715 0.7164 0.108 Uiso 1 1 calc R . .
H25B H -0.2843 0.0911 0.8204 0.108 Uiso 1 1 calc R . .
C26 C -0.4225(4) 0.13221(11) 0.7376(4) 0.1082(11) Uani 1 1 d . . .
H26A H -0.3588 0.1553 0.7364 0.162 Uiso 1 1 calc R . .
H26B H -0.4724 0.1320 0.8426 0.162 Uiso 1 1 calc R . .
H26C H -0.4886 0.1346 0.6448 0.162 Uiso 1 1 calc R . .
C27 C -0.15309(19) 0.06772(5) 0.2588(2) 0.0447(4) Uani 1 1 d . . .
C28 C -0.2622(3) 0.01060(7) 0.1198(3) 0.0696(6) Uani 1 1 d . . .
H28A H -0.3553 0.0228 0.1104 0.084 Uiso 1 1 calc R . .
H28B H -0.2118 0.0167 0.0167 0.084 Uiso 1 1 calc R . .
C29 C -0.2738(5) -0.03349(10) 0.1416(5) 0.1252(15) Uani 1 1 d . . .
H29A H -0.1825 -0.0460 0.1310 0.188 Uiso 1 1 calc R . .
H29B H -0.3365 -0.0446 0.0565 0.188 Uiso 1 1 calc R . .
H29C H -0.3100 -0.0394 0.2520 0.188 Uiso 1 1 calc R . .
Cl1 Cl 0.38993(6) 0.023200(15) 0.34043(9) 0.0712(2) Uani 1 1 d . . .
O1 O -0.10662(18) 0.05288(5) 0.6904(2) 0.0691(4) Uani 1 1 d . . .
O2 O -0.26009(17) 0.09558(5) 0.5682(2) 0.0662(4) Uani 1 1 d . . .
O3 O -0.1909(2) 0.09034(5) 0.1481(2) 0.0735(5) Uani 1 1 d . . .
O4 O -0.18670(17) 0.02792(4) 0.2653(2) 0.0619(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C24 1.522(3) . ?
C1 C27 1.528(3) . ?
C1 C9 1.558(2) . ?
C1 C2 1.556(2) . ?
C2 C3 1.494(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.377(3) . ?
C3 C8 1.390(2) . ?
C4 C5 1.376(3) . ?
C4 Cl1 1.7425(18) . ?
C5 C6 1.401(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.417(2) . ?
C6 C10 1.482(2) . ?
C7 C8 1.401(2) . ?
C7 C16 1.432(2) . ?
C8 C9 1.502(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.390(3) . ?
C10 C11 1.396(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.195(2) . ?
C17 C18 1.433(2) . ?
C18 C23 1.386(3) . ?
C18 C19 1.390(3) . ?
C19 C20 1.384(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O1 1.190(2) . ?
C24 O2 1.322(2) . ?
C25 C26 1.419(4) . ?
C25 O2 1.467(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 O3 1.189(2) . ?
C27 O4 1.324(2) . ?
C28 C29 1.437(4) . ?
C28 O4 1.455(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C24 C1 C27 108.83(15) . . ?
C24 C1 C9 110.53(15) . . ?
C27 C1 C9 110.37(15) . . ?
C24 C1 C2 111.21(16) . . ?
C27 C1 C2 109.45(16) . . ?
C9 C1 C2 106.44(14) . . ?
C3 C2 C1 104.05(14) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C8 118.55(16) . . ?
C4 C3 C2 129.04(16) . . ?
C8 C3 C2 112.38(15) . . ?
C5 C4 C3 121.50(16) . . ?
C5 C4 Cl1 119.35(14) . . ?
C3 C4 Cl1 119.14(14) . . ?
C4 C5 C6 120.92(17) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 118.44(16) . . ?
C5 C6 C10 119.12(16) . . ?
C7 C6 C10 122.41(15) . . ?
C8 C7 C6 118.84(15) . . ?
C8 C7 C16 119.31(15) . . ?
C6 C7 C16 121.77(15) . . ?
C3 C8 C7 121.67(16) . . ?
C3 C8 C9 110.89(15) . . ?
C7 C8 C9 127.42(15) . . ?
C8 C9 C1 104.53(13) . . ?
C8 C9 H9A 110.8 . . ?
C1 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C1 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C15 C10 C11 117.98(17) . . ?
C15 C10 C6 121.57(16) . . ?
C11 C10 C6 120.45(16) . . ?
C12 C11 C10 120.43(18) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.65(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.70(19) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.94(19) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 C16 C7 178.2(2) . . ?
C16 C17 C18 175.53(19) . . ?
C23 C18 C19 118.78(17) . . ?
C23 C18 C17 121.16(16) . . ?
C19 C18 C17 119.98(17) . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 119.68(19) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.74(19) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
O1 C24 O2 123.67(19) . . ?
O1 C24 C1 125.52(18) . . ?
O2 C24 C1 110.76(16) . . ?
C26 C25 O2 110.5(2) . . ?
C26 C25 H25A 109.5 . . ?
O2 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O3 C27 O4 123.59(19) . . ?
O3 C27 C1 125.85(17) . . ?
O4 C27 C1 110.57(15) . . ?
C29 C28 O4 108.9(2) . . ?
C29 C28 H28A 109.9 . . ?
O4 C28 H28A 109.9 . . ?
C29 C28 H28B 109.9 . . ?
O4 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 O2 C25 116.38(19) . . ?
C27 O4 C28 117.24(17) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 901559'
#######################################################################
#
#                 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_120109a_0m
#TrackingRef '120109a_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H33 Cl O4'
_chemical_formula_weight         529.04

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

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'
'-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                   12.1117(9)
_cell_length_b                   15.1500(12)
_cell_length_c                   31.225(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5729.6(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47424
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.66
_reflns_number_total             6659
_reflns_number_gt                4184
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0835P)²+1.6385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6659
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1801
_refine_ls_wR_factor_gt          0.1541
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38530(16) 0.34408(13) 0.37104(6) 0.0491(4) Uani 1 1 d . . .
C2 C 0.49241(17) 0.30790(14) 0.36972(6) 0.0523(5) Uani 1 1 d . . .
C3 C 0.50634(18) 0.22414(14) 0.35214(7) 0.0594(5) Uani 1 1 d . . .
H3 H 0.5764 0.1990 0.3515 0.071 Uiso 1 1 calc R . .
C4 C 0.41832(19) 0.17785(14) 0.33563(7) 0.0587(5) Uani 1 1 d . . .
C5 C 0.31343(17) 0.21361(13) 0.33544(6) 0.0526(5) Uani 1 1 d . . .
C6 C 0.29799(16) 0.29619(13) 0.35320(6) 0.0497(5) Uani 1 1 d . . .
C7 C 0.17842(17) 0.32229(16) 0.35219(7) 0.0607(5) Uani 1 1 d . . .
H7A H 0.1693 0.3803 0.3395 0.073 Uiso 1 1 calc R . .
H7B H 0.1473 0.3228 0.3808 0.073 Uiso 1 1 calc R . .
C8 C 0.12249(17) 0.25007(15) 0.32401(6) 0.0571(5) Uani 1 1 d . . .
C9 C 0.20761(19) 0.17410(15) 0.32000(7) 0.0619(5) Uani 1 1 d . . .
H9A H 0.1864 0.1242 0.3376 0.074 Uiso 1 1 calc R . .
H9B H 0.2142 0.1547 0.2905 0.074 Uiso 1 1 calc R . .
C10 C 0.09566(19) 0.28809(16) 0.28026(7) 0.0624(6) Uani 1 1 d . . .
C11 C -0.0262(3) 0.3806(2) 0.24168(8) 0.0962(9) Uani 1 1 d . . .
H11A H 0.0312 0.4188 0.2305 0.115 Uiso 1 1 calc R . .
H11B H -0.0392 0.3339 0.2210 0.115 Uiso 1 1 calc R . .
C12 C -0.1259(3) 0.4306(2) 0.24777(11) 0.1076(10) Uani 1 1 d . . .
H12A H -0.1839 0.3919 0.2572 0.161 Uiso 1 1 calc R . .
H12B H -0.1469 0.4578 0.2212 0.161 Uiso 1 1 calc R . .
H12C H -0.1137 0.4754 0.2690 0.161 Uiso 1 1 calc R . .
C13 C 0.0164(2) 0.21670(18) 0.34425(8) 0.0693(6) Uani 1 1 d . . .
C14 C -0.1244(3) 0.1064(4) 0.33757(13) 0.1469(18) Uani 1 1 d . . .
H14A H -0.1064 0.0458 0.3448 0.176 Uiso 1 1 calc R . .
H14B H -0.1500 0.1357 0.3633 0.176 Uiso 1 1 calc R . .
C15 C -0.2031(3) 0.1077(4) 0.30814(18) 0.162(2) Uani 1 1 d . . .
H15A H -0.2117 0.1667 0.2974 0.244 Uiso 1 1 calc R . .
H15B H -0.2714 0.0884 0.3206 0.244 Uiso 1 1 calc R . .
H15C H -0.1834 0.0690 0.2850 0.244 Uiso 1 1 calc R . .
C16 C 0.36204(16) 0.42838(14) 0.38984(6) 0.0521(5) Uani 1 1 d . . .
C17 C 0.33686(18) 0.49586(14) 0.40704(6) 0.0562(5) Uani 1 1 d . . .
C18 C 0.31060(19) 0.57644(14) 0.42896(6) 0.0567(5) Uani 1 1 d . . .
C19 C 0.2017(2) 0.60608(16) 0.43189(7) 0.0665(6) Uani 1 1 d . . .
H19 H 0.1454 0.5730 0.4196 0.080 Uiso 1 1 calc R . .
C20 C 0.1766(2) 0.68368(17) 0.45279(8) 0.0758(7) Uani 1 1 d . . .
H20 H 0.1035 0.7023 0.4542 0.091 Uiso 1 1 calc R . .
C21 C 0.2577(3) 0.73408(16) 0.47162(7) 0.0745(7) Uani 1 1 d . . .
C22 C 0.3648(3) 0.70468(17) 0.46872(8) 0.0813(7) Uani 1 1 d . . .
H22 H 0.4207 0.7378 0.4813 0.098 Uiso 1 1 calc R . .
C23 C 0.3917(2) 0.62741(17) 0.44769(8) 0.0700(6) Uani 1 1 d . . .
H23 H 0.4651 0.6096 0.4461 0.084 Uiso 1 1 calc R . .
C24 C 0.2300(3) 0.81828(17) 0.49542(9) 0.1034(11) Uani 1 1 d . . .
H24A H 0.2875 0.8615 0.4901 0.124 Uiso 1 1 calc R . .
H24B H 0.1614 0.8419 0.4843 0.124 Uiso 1 1 calc R . .
C25 C 0.2189(3) 0.80551(19) 0.54209(9) 0.1023(10) Uani 1 1 d . . .
H25A H 0.1646 0.7607 0.5476 0.153 Uiso 1 1 calc R . .
H25B H 0.1961 0.8599 0.5552 0.153 Uiso 1 1 calc R . .
H25C H 0.2886 0.7876 0.5538 0.153 Uiso 1 1 calc R . .
C26 C 0.59174(17) 0.35598(14) 0.38535(7) 0.0556(5) Uani 1 1 d . . .
C27 C 0.59643(19) 0.39665(16) 0.42515(7) 0.0631(6) Uani 1 1 d . . .
H27 H 0.5345 0.3961 0.4428 0.076 Uiso 1 1 calc R . .
C28 C 0.6917(2) 0.43798(16) 0.43898(8) 0.0709(6) Uani 1 1 d . . .
H28 H 0.6929 0.4640 0.4660 0.085 Uiso 1 1 calc R . .
C29 C 0.7851(2) 0.44156(16) 0.41373(9) 0.0723(6) Uani 1 1 d . . .
C30 C 0.7811(2) 0.40131(18) 0.37402(9) 0.0740(7) Uani 1 1 d . . .
H30 H 0.8429 0.4027 0.3564 0.089 Uiso 1 1 calc R . .
C31 C 0.68633(18) 0.35891(16) 0.36012(8) 0.0652(6) Uani 1 1 d . . .
H31 H 0.6859 0.3319 0.3334 0.078 Uiso 1 1 calc R . .
C32 C 0.8909(2) 0.4857(2) 0.42907(12) 0.0957(9) Uani 1 1 d . . .
H32A H 0.9267 0.5136 0.4048 0.115 Uiso 1 1 calc R . .
H32B H 0.8718 0.5318 0.4493 0.115 Uiso 1 1 calc R . .
C33 C 0.9684(3) 0.4258(2) 0.44920(12) 0.1122(11) Uani 1 1 d . . .
H33A H 0.9347 0.3994 0.4739 0.168 Uiso 1 1 calc R . .
H33B H 1.0331 0.4579 0.4578 0.168 Uiso 1 1 calc R . .
H33C H 0.9889 0.3805 0.4292 0.168 Uiso 1 1 calc R . .
Cl1 Cl 0.43851(6) 0.07174(4) 0.31563(2) 0.0870(3) Uani 1 1 d . . .
O1 O 0.14581(17) 0.27303(15) 0.24824(5) 0.0974(7) Uani 1 1 d . . .
O2 O 0.00989(14) 0.34233(12) 0.28193(5) 0.0753(5) Uani 1 1 d . . .
O3 O -0.02278(16) 0.24190(15) 0.37672(6) 0.0913(6) Uani 1 1 d . . .
O4 O -0.02493(19) 0.15168(18) 0.32105(7) 0.1157(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.398(3) . ?
C1 C2 1.409(3) . ?
C1 C16 1.434(3) . ?
C2 C3 1.393(3) . ?
C2 C26 1.489(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.381(3) . ?
C4 Cl1 1.742(2) . ?
C5 C6 1.381(3) . ?
C5 C9 1.494(3) . ?
C6 C7 1.501(3) . ?
C7 C8 1.559(3) . ?
C8 C10 1.518(3) . ?
C8 C13 1.519(3) . ?
C8 C9 1.550(3) . ?
C10 O1 1.192(3) . ?
C10 O2 1.326(3) . ?
C11 C12 1.439(4) . ?
C11 O2 1.451(3) . ?
C13 O3 1.183(3) . ?
C13 O4 1.321(3) . ?
C14 C15 1.325(5) . ?
C14 O4 1.479(4) . ?
C16 C17 1.194(3) . ?
C17 C18 1.435(3) . ?
C18 C23 1.379(3) . ?
C18 C19 1.396(3) . ?
C19 C20 1.379(3) . ?
C20 C21 1.377(4) . ?
C21 C22 1.373(4) . ?
C21 C24 1.514(3) . ?
C22 C23 1.381(3) . ?
C24 C25 1.476(4) . ?
C26 C27 1.388(3) . ?
C26 C31 1.391(3) . ?
C27 C28 1.382(3) . ?
C28 C29 1.380(4) . ?
C29 C30 1.383(4) . ?
C29 C32 1.522(4) . ?
C30 C31 1.385(3) . ?
C32 C33 1.450(4) . ?

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
C6 C1 C2 118.87(18) . . ?
C6 C1 C16 118.48(17) . . ?
C2 C1 C16 122.66(18) . . ?
C3 C2 C1 118.53(19) . . ?
C3 C2 C26 118.49(18) . . ?
C1 C2 C26 122.96(18) . . ?
C4 C3 C2 121.2(2) . . ?
C3 C4 C5 120.95(19) . . ?
C3 C4 Cl1 119.72(17) . . ?
C5 C4 Cl1 119.32(17) . . ?
C6 C5 C4 118.56(19) . . ?
C6 C5 C9 112.10(18) . . ?
C4 C5 C9 129.28(19) . . ?
C5 C6 C1 121.84(18) . . ?
C5 C6 C7 111.15(18) . . ?
C1 C6 C7 126.95(18) . . ?
C6 C7 C8 104.25(17) . . ?
C10 C8 C13 108.65(18) . . ?
C10 C8 C9 110.58(17) . . ?
C13 C8 C9 110.4(2) . . ?
C10 C8 C7 109.56(19) . . ?
C13 C8 C7 111.49(18) . . ?
C9 C8 C7 106.11(17) . . ?
C5 C9 C8 104.30(17) . . ?
O1 C10 O2 123.4(2) . . ?
O1 C10 C8 125.0(2) . . ?
O2 C10 C8 111.57(18) . . ?
C12 C11 O2 110.4(2) . . ?
O3 C13 O4 124.0(2) . . ?
O3 C13 C8 126.1(2) . . ?
O4 C13 C8 109.9(2) . . ?
C15 C14 O4 109.7(4) . . ?
C17 C16 C1 175.4(2) . . ?
C16 C17 C18 177.5(2) . . ?
C23 C18 C19 117.7(2) . . ?
C23 C18 C17 121.4(2) . . ?
C19 C18 C17 120.9(2) . . ?
C20 C19 C18 120.9(2) . . ?
C21 C20 C19 121.1(3) . . ?
C22 C21 C20 117.8(2) . . ?
C22 C21 C24 121.0(3) . . ?
C20 C21 C24 121.2(3) . . ?
C21 C22 C23 121.9(2) . . ?
C18 C23 C22 120.5(2) . . ?
C25 C24 C21 113.2(2) . . ?
C27 C26 C31 117.3(2) . . ?
C27 C26 C2 122.94(19) . . ?
C31 C26 C2 119.70(19) . . ?
C28 C27 C26 121.0(2) . . ?
C29 C28 C27 121.6(2) . . ?
C28 C29 C30 117.8(2) . . ?
C28 C29 C32 121.8(3) . . ?
C30 C29 C32 120.4(3) . . ?
C29 C30 C31 121.0(2) . . ?
C30 C31 C26 121.3(2) . . ?
C33 C32 C29 114.0(3) . . ?
C10 O2 C11 116.70(19) . . ?
C13 O4 C14 117.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 901560'
