# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# 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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# 
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#  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 
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data_t
_database_code_depnum_ccdc_archive 'CCDC 884836'
#TrackingRef 'web_deposit_cif_file_0_YanYang_1338480001.(Z)-2-(4-methylbenzylidene)-1-phenylbutane-1,3-dione.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31

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'

_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                   30.156(7)
_cell_length_b                   8.795(2)
_cell_length_c                   11.162(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.061(4)
_cell_angle_gamma                90.00
_cell_volume                     2915.0(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6836
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.53

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9908
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20152
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         0.69
_diffrn_reflns_theta_max         26.59
_reflns_number_total             6043
_reflns_number_gt                4616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0714P)^2^+0.9677P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0040(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         6043
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1572
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.50073(7) 0.1707(2) -0.1137(2) 0.0606(5) Uani 1 1 d . . .
H1A H 0.4831 0.0823 -0.1410 0.091 Uiso 1 1 calc R . .
H1B H 0.5242 0.1433 -0.0476 0.091 Uiso 1 1 calc R . .
H1C H 0.5138 0.2107 -0.1796 0.091 Uiso 1 1 calc R . .
C2 C 0.47099(6) 0.2891(2) -0.07159(16) 0.0459(4) Uani 1 1 d . . .
C3 C 0.45262(7) 0.2683(2) 0.03261(17) 0.0510(4) Uani 1 1 d . . .
H3 H 0.4584 0.1780 0.0759 0.061 Uiso 1 1 calc R . .
C4 C 0.42618(7) 0.3764(2) 0.07417(16) 0.0493(4) Uani 1 1 d . . .
H4 H 0.4145 0.3584 0.1447 0.059 Uiso 1 1 calc R . .
C5 C 0.41660(6) 0.51351(19) 0.01143(15) 0.0419(4) Uani 1 1 d . . .
C6 C 0.43460(7) 0.5333(2) -0.09391(16) 0.0496(4) Uani 1 1 d . . .
H6 H 0.4285 0.6225 -0.1385 0.060 Uiso 1 1 calc R . .
C7 C 0.46129(7) 0.4239(2) -0.13386(16) 0.0517(5) Uani 1 1 d . . .
H7 H 0.4730 0.4413 -0.2043 0.062 Uiso 1 1 calc R . .
C8 C 0.39006(6) 0.6384(2) 0.04875(15) 0.0449(4) Uani 1 1 d . . .
H8 H 0.3860 0.7200 -0.0050 0.054 Uiso 1 1 calc R . .
C9 C 0.37055(6) 0.65569(19) 0.14727(15) 0.0433(4) Uani 1 1 d . . .
C10 C 0.34574(7) 0.7958(2) 0.16836(18) 0.0515(5) Uani 1 1 d . . .
C11 C 0.34399(11) 0.9286(3) 0.0833(3) 0.0848(8) Uani 1 1 d . . .
H11A H 0.3236 1.0038 0.1045 0.127 Uiso 1 1 calc R . .
H11B H 0.3337 0.8950 0.0013 0.127 Uiso 1 1 calc R . .
H11C H 0.3735 0.9720 0.0896 0.127 Uiso 1 1 calc R . .
C12 C 0.37287(6) 0.54286(19) 0.24964(15) 0.0431(4) Uani 1 1 d . . .
C13 C 0.33785(6) 0.4227(2) 0.24097(15) 0.0434(4) Uani 1 1 d . . .
C14 C 0.34195(8) 0.3090(2) 0.32770(19) 0.0619(5) Uani 1 1 d . . .
H14 H 0.3663 0.3093 0.3917 0.074 Uiso 1 1 calc R . .
C15 C 0.31028(10) 0.1955(3) 0.3198(3) 0.0801(7) Uani 1 1 d . . .
H15 H 0.3136 0.1187 0.3780 0.096 Uiso 1 1 calc R . .
C16 C 0.27413(9) 0.1942(3) 0.2276(3) 0.0787(7) Uani 1 1 d . . .
H16 H 0.2528 0.1172 0.2234 0.094 Uiso 1 1 calc R . .
C17 C 0.26921(8) 0.3061(3) 0.1413(3) 0.0768(7) Uani 1 1 d . . .
H17 H 0.2445 0.3057 0.0786 0.092 Uiso 1 1 calc R . .
C18 C 0.30142(7) 0.4203(2) 0.14779(19) 0.0589(5) Uani 1 1 d . . .
H18 H 0.2983 0.4958 0.0886 0.071 Uiso 1 1 calc R . .
C19 C 0.00253(7) 0.8313(2) -0.11509(19) 0.0622(5) Uani 1 1 d . . .
H19A H -0.0106 0.7931 -0.1939 0.093 Uiso 1 1 calc R . .
H19B H 0.0208 0.9185 -0.1244 0.093 Uiso 1 1 calc R . .
H19C H -0.0209 0.8597 -0.0713 0.093 Uiso 1 1 calc R . .
C20 C 0.03128(6) 0.7101(2) -0.04574(16) 0.0469(4) Uani 1 1 d . . .
C21 C 0.03871(7) 0.5723(2) -0.09812(16) 0.0532(5) Uani 1 1 d . . .
H21 H 0.0263 0.5550 -0.1793 0.064 Uiso 1 1 calc R . .
C22 C 0.06407(7) 0.4596(2) -0.03297(16) 0.0503(4) Uani 1 1 d . . .
H22 H 0.0683 0.3679 -0.0710 0.060 Uiso 1 1 calc R . .
C23 C 0.08351(6) 0.4802(2) 0.08839(15) 0.0426(4) Uani 1 1 d . . .
C24 C 0.07652(7) 0.6205(2) 0.14081(16) 0.0514(5) Uani 1 1 d . . .
H24 H 0.0893 0.6390 0.2215 0.062 Uiso 1 1 calc R . .
C25 C 0.05107(7) 0.7315(2) 0.07469(17) 0.0531(5) Uani 1 1 d . . .
H25 H 0.0470 0.8238 0.1120 0.064 Uiso 1 1 calc R . .
C26 C 0.10841(6) 0.3524(2) 0.15079(16) 0.0455(4) Uani 1 1 d . . .
H26 H 0.1109 0.2690 0.1013 0.055 Uiso 1 1 calc R . .
C27 C 0.12834(6) 0.3343(2) 0.26748(15) 0.0433(4) Uani 1 1 d . . .
C28 C 0.15183(7) 0.1921(2) 0.31176(18) 0.0525(5) Uani 1 1 d . . .
C29 C 0.15047(10) 0.0570(3) 0.2302(2) 0.0814(8) Uani 1 1 d . . .
H29A H 0.1683 -0.0233 0.2724 0.122 Uiso 1 1 calc R . .
H29B H 0.1623 0.0843 0.1587 0.122 Uiso 1 1 calc R . .
H29C H 0.1199 0.0232 0.2071 0.122 Uiso 1 1 calc R . .
C30 C 0.12849(6) 0.4510(2) 0.36659(15) 0.0444(4) Uani 1 1 d . . .
C31 C 0.16530(6) 0.5646(2) 0.38694(15) 0.0461(4) Uani 1 1 d . . .
C32 C 0.20088(7) 0.5554(3) 0.3253(2) 0.0659(6) Uani 1 1 d . . .
H32 H 0.2022 0.4756 0.2713 0.079 Uiso 1 1 calc R . .
C33 C 0.23471(9) 0.6634(3) 0.3427(3) 0.0887(8) Uani 1 1 d . . .
H33 H 0.2588 0.6556 0.3011 0.106 Uiso 1 1 calc R . .
C34 C 0.23282(10) 0.7800(3) 0.4203(3) 0.0906(9) Uani 1 1 d . . .
H34 H 0.2554 0.8534 0.4307 0.109 Uiso 1 1 calc R . .
C35 C 0.19782(11) 0.7914(3) 0.4839(2) 0.0867(8) Uani 1 1 d . . .
H35 H 0.1971 0.8712 0.5382 0.104 Uiso 1 1 calc R . .
C36 C 0.16348(9) 0.6836(2) 0.46720(19) 0.0654(6) Uani 1 1 d . . .
H36 H 0.1396 0.6915 0.5094 0.079 Uiso 1 1 calc R . .
O1 O 0.32713(5) 0.80169(16) 0.25729(14) 0.0664(4) Uani 1 1 d . . .
O2 O 0.40293(5) 0.55341(16) 0.33723(12) 0.0592(4) Uani 1 1 d . . .
O3 O 0.17234(6) 0.18745(17) 0.41591(14) 0.0722(5) Uani 1 1 d . . .
O4 O 0.09872(5) 0.44772(17) 0.42776(12) 0.0613(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0625(12) 0.0573(12) 0.0658(12) -0.0123(10) 0.0215(10) 0.0045(10)
C2 0.0460(9) 0.0479(10) 0.0439(9) -0.0089(7) 0.0081(7) -0.0012(8)
C3 0.0620(11) 0.0442(10) 0.0485(10) 0.0048(8) 0.0148(9) 0.0082(9)
C4 0.0599(11) 0.0485(10) 0.0434(9) 0.0048(8) 0.0201(8) 0.0047(9)
C5 0.0445(9) 0.0430(9) 0.0384(8) -0.0005(7) 0.0074(7) 0.0010(7)
C6 0.0602(11) 0.0483(10) 0.0420(9) 0.0048(8) 0.0130(8) 0.0039(8)
C7 0.0618(12) 0.0558(11) 0.0414(9) -0.0031(8) 0.0197(8) -0.0027(9)
C8 0.0500(10) 0.0419(9) 0.0434(9) 0.0029(7) 0.0095(8) 0.0016(8)
C9 0.0462(9) 0.0410(9) 0.0433(9) -0.0010(7) 0.0093(7) 0.0012(7)
C10 0.0554(11) 0.0470(10) 0.0546(11) -0.0016(8) 0.0164(9) 0.0027(8)
C11 0.116(2) 0.0561(13) 0.0928(18) 0.0180(12) 0.0487(16) 0.0297(14)
C12 0.0467(9) 0.0457(9) 0.0377(8) -0.0035(7) 0.0097(7) 0.0068(7)
C13 0.0489(10) 0.0452(9) 0.0384(8) -0.0012(7) 0.0140(7) 0.0056(8)
C14 0.0734(14) 0.0597(12) 0.0534(11) 0.0093(9) 0.0131(10) 0.0020(11)
C15 0.100(2) 0.0607(14) 0.0856(17) 0.0147(12) 0.0342(16) -0.0070(13)
C16 0.0697(15) 0.0615(14) 0.112(2) -0.0054(14) 0.0355(15) -0.0138(12)
C17 0.0543(13) 0.0805(17) 0.0918(17) -0.0118(14) 0.0021(12) -0.0040(12)
C18 0.0559(12) 0.0576(12) 0.0602(12) 0.0040(9) 0.0014(9) 0.0014(10)
C19 0.0629(13) 0.0581(12) 0.0602(12) 0.0132(10) -0.0039(10) 0.0033(10)
C20 0.0443(9) 0.0500(10) 0.0449(9) 0.0084(8) 0.0039(8) -0.0026(8)
C21 0.0593(11) 0.0586(11) 0.0378(9) 0.0003(8) -0.0022(8) -0.0009(9)
C22 0.0585(11) 0.0495(10) 0.0412(9) -0.0061(8) 0.0042(8) 0.0021(8)
C23 0.0418(9) 0.0464(9) 0.0389(8) 0.0000(7) 0.0045(7) -0.0028(7)
C24 0.0590(11) 0.0512(10) 0.0397(9) -0.0034(8) -0.0032(8) 0.0022(9)
C25 0.0622(11) 0.0445(10) 0.0499(10) -0.0017(8) 0.0019(9) 0.0050(9)
C26 0.0460(9) 0.0437(9) 0.0453(9) -0.0048(7) 0.0040(8) -0.0012(8)
C27 0.0410(9) 0.0431(9) 0.0444(9) -0.0002(7) 0.0036(7) -0.0012(7)
C28 0.0514(10) 0.0496(11) 0.0530(11) 0.0024(8) -0.0008(9) 0.0028(8)
C29 0.0974(19) 0.0556(13) 0.0807(16) -0.0103(11) -0.0138(14) 0.0215(13)
C30 0.0476(10) 0.0478(9) 0.0373(8) 0.0063(7) 0.0055(7) 0.0059(8)
C31 0.0528(10) 0.0475(10) 0.0349(8) -0.0004(7) -0.0007(7) 0.0003(8)
C32 0.0539(12) 0.0717(14) 0.0729(14) -0.0193(11) 0.0129(10) -0.0116(10)
C33 0.0619(15) 0.099(2) 0.105(2) -0.0187(17) 0.0144(14) -0.0271(14)
C34 0.0913(19) 0.0859(19) 0.0856(18) -0.0080(15) -0.0090(16) -0.0378(16)
C35 0.127(2) 0.0611(14) 0.0648(14) -0.0165(11) -0.0030(16) -0.0188(15)
C36 0.0905(16) 0.0551(12) 0.0500(11) -0.0061(9) 0.0102(11) 0.0032(11)
O1 0.0787(10) 0.0568(9) 0.0729(9) -0.0036(7) 0.0386(8) 0.0072(7)
O2 0.0613(8) 0.0667(9) 0.0452(7) -0.0032(6) -0.0026(6) -0.0010(7)
O3 0.0814(10) 0.0636(9) 0.0616(9) 0.0060(7) -0.0157(8) 0.0094(8)
O4 0.0647(9) 0.0687(9) 0.0552(8) 0.0047(7) 0.0231(7) 0.0015(7)

_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 C2 1.503(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.380(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(2) . ?
C5 C8 1.462(2) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.343(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.481(2) . ?
C9 C12 1.506(2) . ?
C10 O1 1.224(2) . ?
C10 C11 1.501(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O2 1.215(2) . ?
C12 C13 1.485(3) . ?
C13 C18 1.375(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.500(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.381(3) . ?
C20 C25 1.385(3) . ?
C21 C22 1.379(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(3) . ?
C23 C26 1.459(2) . ?
C24 C25 1.374(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.345(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.479(2) . ?
C27 C30 1.508(2) . ?
C28 O3 1.218(2) . ?
C28 C29 1.493(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 O4 1.220(2) . ?
C30 C31 1.481(3) . ?
C31 C32 1.374(3) . ?
C31 C36 1.385(3) . ?
C32 C33 1.383(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.350(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.375(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.393(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.14(17) . . ?
C7 C2 C1 121.58(17) . . ?
C3 C2 C1 121.28(18) . . ?
C4 C3 C2 122.21(17) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 120.62(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 117.03(16) . . ?
C6 C5 C8 117.47(16) . . ?
C4 C5 C8 125.49(15) . . ?
C7 C6 C5 121.56(17) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 121.43(17) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C9 C8 C5 131.15(16) . . ?
C9 C8 H8 114.4 . . ?
C5 C8 H8 114.4 . . ?
C8 C9 C10 121.99(16) . . ?
C8 C9 C12 125.29(16) . . ?
C10 C9 C12 112.66(15) . . ?
O1 C10 C9 118.71(17) . . ?
O1 C10 C11 120.64(18) . . ?
C9 C10 C11 120.65(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 121.93(16) . . ?
O2 C12 C9 119.30(17) . . ?
C13 C12 C9 118.77(15) . . ?
C18 C13 C14 118.74(19) . . ?
C18 C13 C12 121.69(16) . . ?
C14 C13 C12 119.57(17) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 120.6(2) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 117.11(16) . . ?
C21 C20 C19 121.79(17) . . ?
C25 C20 C19 121.09(18) . . ?
C22 C21 C20 121.57(16) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 121.38(17) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C24 117.01(16) . . ?
C22 C23 C26 117.31(16) . . ?
C24 C23 C26 125.66(15) . . ?
C25 C24 C23 120.89(16) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C20 122.03(18) . . ?
C24 C25 H25 119.0 . . ?
C20 C25 H25 119.0 . . ?
C27 C26 C23 131.22(17) . . ?
C27 C26 H26 114.4 . . ?
C23 C26 H26 114.4 . . ?
C26 C27 C28 122.04(16) . . ?
C26 C27 C30 124.98(16) . . ?
C28 C27 C30 112.97(14) . . ?
O3 C28 C27 118.74(18) . . ?
O3 C28 C29 120.69(18) . . ?
C27 C28 C29 120.57(17) . . ?
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 . . ?
O4 C30 C31 122.38(17) . . ?
O4 C30 C27 119.09(17) . . ?
C31 C30 C27 118.53(15) . . ?
C32 C31 C36 119.40(19) . . ?
C32 C31 C30 120.88(17) . . ?
C36 C31 C30 119.71(19) . . ?
C31 C32 C33 120.7(2) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C34 C33 C32 120.0(3) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.6(2) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C36 120.1(2) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C31 C36 C35 119.3(2) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?

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
C7 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 C4 178.54(19) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C8 -178.11(18) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C8 C5 C6 C7 177.80(18) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
C1 C2 C7 C6 -178.96(18) . . . . ?
C6 C5 C8 C9 -176.44(19) . . . . ?
C4 C5 C8 C9 2.3(3) . . . . ?
C5 C8 C9 C10 178.50(18) . . . . ?
C5 C8 C9 C12 1.5(3) . . . . ?
C8 C9 C10 O1 176.95(18) . . . . ?
C12 C9 C10 O1 -5.7(3) . . . . ?
C8 C9 C10 C11 -3.9(3) . . . . ?
C12 C9 C10 C11 173.5(2) . . . . ?
C8 C9 C12 O2 91.0(2) . . . . ?
C10 C9 C12 O2 -86.2(2) . . . . ?
C8 C9 C12 C13 -89.7(2) . . . . ?
C10 C9 C12 C13 93.09(19) . . . . ?
O2 C12 C13 C18 173.35(18) . . . . ?
C9 C12 C13 C18 -5.9(2) . . . . ?
O2 C12 C13 C14 -7.4(3) . . . . ?
C9 C12 C13 C14 173.38(17) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
C12 C13 C14 C15 -178.8(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C12 C13 C18 C17 179.62(19) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
C25 C20 C21 C22 1.1(3) . . . . ?
C19 C20 C21 C22 -178.06(19) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C21 C22 C23 C26 177.89(18) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C26 C23 C24 C25 -177.58(19) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?
C21 C20 C25 C24 -0.9(3) . . . . ?
C19 C20 C25 C24 178.24(19) . . . . ?
C22 C23 C26 C27 -175.62(19) . . . . ?
C24 C23 C26 C27 2.7(3) . . . . ?
C23 C26 C27 C28 179.53(18) . . . . ?
C23 C26 C27 C30 1.1(3) . . . . ?
C26 C27 C28 O3 174.03(19) . . . . ?
C30 C27 C28 O3 -7.4(3) . . . . ?
C26 C27 C28 C29 -5.9(3) . . . . ?
C30 C27 C28 C29 172.7(2) . . . . ?
C26 C27 C30 O4 91.4(2) . . . . ?
C28 C27 C30 O4 -87.1(2) . . . . ?
C26 C27 C30 C31 -89.3(2) . . . . ?
C28 C27 C30 C31 92.14(19) . . . . ?
O4 C30 C31 C32 173.03(19) . . . . ?
C27 C30 C31 C32 -6.2(3) . . . . ?
O4 C30 C31 C36 -8.3(3) . . . . ?
C27 C30 C31 C36 172.42(17) . . . . ?
C36 C31 C32 C33 0.0(3) . . . . ?
C30 C31 C32 C33 178.7(2) . . . . ?
C31 C32 C33 C34 -0.5(4) . . . . ?
C32 C33 C34 C35 1.1(5) . . . . ?
C33 C34 C35 C36 -1.2(4) . . . . ?
C32 C31 C36 C35 -0.1(3) . . . . ?
C30 C31 C36 C35 -178.78(19) . . . . ?
C34 C35 C36 C31 0.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.59
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036


data_mo_120314f_0m
_database_code_depnum_ccdc_archive 'CCDC 884837'
#TrackingRef 'web_deposit_cif_file_1_YanYang_1338480001.(Z)-2-(4-fluorobenzylidene)-1-phenylbutane-1,3-dione.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 F O2'
_chemical_formula_weight         268.27

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   9.0702(12)
_cell_length_b                   15.872(2)
_cell_length_c                   19.619(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2824.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5759
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      23.71

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9892
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20476
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3242
_reflns_number_gt                2328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0677P)^2^+0.4112P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0034(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3242
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 1.32606(18) 0.46248(11) 0.15177(10) 0.0700(5) Uani 1 1 d . . .
C2 C 1.35457(19) 0.45198(14) 0.08452(11) 0.0871(6) Uani 1 1 d . . .
H2 H 1.4482 0.4621 0.0670 0.104 Uiso 1 1 calc R . .
C3 C 1.24111(18) 0.42580(13) 0.04265(9) 0.0736(5) Uani 1 1 d . . .
H3 H 1.2596 0.4182 -0.0036 0.088 Uiso 1 1 calc R . .
C4 C 1.10085(16) 0.41055(9) 0.06732(8) 0.0575(4) Uani 1 1 d . . .
C5 C 1.0790(2) 0.42368(16) 0.13678(10) 0.0909(6) Uani 1 1 d . . .
H5 H 0.9856 0.4149 0.1550 0.109 Uiso 1 1 calc R . .
C6 C 1.1911(2) 0.44926(15) 0.17920(10) 0.0882(6) Uani 1 1 d . . .
H6 H 1.1745 0.4573 0.2255 0.106 Uiso 1 1 calc R . .
C7 C 0.98929(18) 0.38192(10) 0.01901(8) 0.0613(4) Uani 1 1 d . . .
H7 H 1.0224 0.3759 -0.0256 0.074 Uiso 1 1 calc R . .
C8 C 0.84660(17) 0.36286(9) 0.02856(8) 0.0559(4) Uani 1 1 d . . .
C9 C 0.7499(2) 0.33339(11) -0.02718(9) 0.0703(5) Uani 1 1 d . . .
C10 C 0.8121(3) 0.31360(17) -0.09598(11) 0.1029(7) Uani 1 1 d . . .
H10A H 0.7341 0.2958 -0.1258 0.154 Uiso 1 1 calc R . .
H10B H 0.8836 0.2693 -0.0919 0.154 Uiso 1 1 calc R . .
H10C H 0.8585 0.3630 -0.1144 0.154 Uiso 1 1 calc R . .
C11 C 0.76552(16) 0.36997(9) 0.09519(8) 0.0545(4) Uani 1 1 d . . .
C12 C 0.73823(16) 0.29153(9) 0.13380(7) 0.0532(4) Uani 1 1 d . . .
C13 C 0.6350(2) 0.29197(14) 0.18599(9) 0.0813(5) Uani 1 1 d . . .
H13 H 0.5860 0.3416 0.1971 0.098 Uiso 1 1 calc R . .
C14 C 0.6053(3) 0.2196(2) 0.22097(12) 0.1159(9) Uani 1 1 d . . .
H14 H 0.5348 0.2200 0.2554 0.139 Uiso 1 1 calc R . .
C15 C 0.6776(4) 0.14727(19) 0.20599(14) 0.1198(10) Uani 1 1 d . . .
H15 H 0.6568 0.0985 0.2304 0.144 Uiso 1 1 calc R . .
C16 C 0.7820(3) 0.14516(12) 0.15483(12) 0.0970(7) Uani 1 1 d . . .
H16 H 0.8314 0.0953 0.1449 0.116 Uiso 1 1 calc R . .
C17 C 0.8125(2) 0.21765(9) 0.11842(8) 0.0657(4) Uani 1 1 d . . .
H17 H 0.8826 0.2168 0.0838 0.079 Uiso 1 1 calc R . .
F1 F 1.43588(11) 0.48813(8) 0.19407(7) 0.1018(4) Uani 1 1 d . . .
O1 O 0.72114(14) 0.43788(7) 0.11484(7) 0.0823(4) Uani 1 1 d . . .
O2 O 0.61893(15) 0.32480(10) -0.01538(8) 0.0940(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0551(8) 0.0711(10) 0.0840(12) -0.0213(9) -0.0023(8) 0.0033(7)
C2 0.0494(9) 0.1172(16) 0.0946(14) -0.0255(12) 0.0154(9) -0.0046(9)
C3 0.0600(9) 0.0954(13) 0.0653(10) -0.0096(9) 0.0134(8) 0.0025(9)
C4 0.0558(8) 0.0579(8) 0.0587(8) 0.0043(7) 0.0075(7) -0.0030(6)
C5 0.0647(10) 0.1400(18) 0.0680(11) -0.0134(11) 0.0164(9) -0.0376(11)
C6 0.0764(12) 0.1243(17) 0.0640(11) -0.0182(10) 0.0098(9) -0.0280(11)
C7 0.0633(9) 0.0663(9) 0.0544(8) 0.0076(7) 0.0069(7) -0.0029(7)
C8 0.0595(8) 0.0489(7) 0.0595(9) 0.0042(6) 0.0003(7) 0.0011(6)
C9 0.0720(11) 0.0703(10) 0.0687(10) 0.0062(8) -0.0089(8) -0.0053(8)
C10 0.1133(17) 0.131(2) 0.0643(11) -0.0108(12) -0.0073(11) -0.0143(15)
C11 0.0485(7) 0.0473(7) 0.0676(9) -0.0060(6) 0.0015(6) 0.0001(6)
C12 0.0561(8) 0.0535(8) 0.0500(8) -0.0028(6) -0.0031(6) -0.0070(6)
C13 0.0798(12) 0.1005(14) 0.0636(10) 0.0013(10) 0.0122(9) -0.0069(10)
C14 0.1193(19) 0.153(2) 0.0758(14) 0.0385(15) 0.0105(13) -0.0335(18)
C15 0.156(3) 0.1106(19) 0.0934(17) 0.0540(15) -0.0327(17) -0.0504(18)
C16 0.144(2) 0.0554(10) 0.0921(15) 0.0133(10) -0.0391(15) -0.0074(11)
C17 0.0859(11) 0.0506(8) 0.0605(9) -0.0014(7) -0.0107(8) 0.0009(7)
F1 0.0627(6) 0.1286(10) 0.1140(9) -0.0501(8) -0.0079(6) -0.0001(6)
O1 0.0763(8) 0.0509(6) 0.1197(11) -0.0152(6) 0.0211(7) 0.0062(5)
O2 0.0723(9) 0.1197(11) 0.0901(10) -0.0017(8) -0.0171(7) -0.0143(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
C1 C6 1.354(2) . ?
C1 C2 1.355(3) . ?
C1 F1 1.3589(19) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(2) . ?
C4 C7 1.459(2) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.342(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.478(2) . ?
C8 C11 1.504(2) . ?
C9 O2 1.218(2) . ?
C9 C10 1.496(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O1 1.2135(17) . ?
C11 C12 1.478(2) . ?
C12 C17 1.386(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.365(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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 122.73(17) . . ?
C6 C1 F1 117.82(17) . . ?
C2 C1 F1 119.45(15) . . ?
C1 C2 C3 118.30(16) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 122.02(16) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 116.58(15) . . ?
C3 C4 C7 117.72(14) . . ?
C5 C4 C7 125.70(14) . . ?
C6 C5 C4 122.08(16) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C1 C6 C5 118.28(18) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C8 C7 C4 130.40(14) . . ?
C8 C7 H7 114.8 . . ?
C4 C7 H7 114.8 . . ?
C7 C8 C9 122.69(15) . . ?
C7 C8 C11 125.16(14) . . ?
C9 C8 C11 112.13(14) . . ?
O2 C9 C8 118.27(17) . . ?
O2 C9 C10 121.03(18) . . ?
C8 C9 C10 120.70(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C12 121.98(14) . . ?
O1 C11 C8 120.33(14) . . ?
C12 C11 C8 117.65(12) . . ?
C17 C12 C13 119.55(16) . . ?
C17 C12 C11 121.30(14) . . ?
C13 C12 C11 119.14(15) . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 119.62(19) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?

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 -0.7(3) . . . . ?
F1 C1 C2 C3 179.95(18) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C4 C7 -179.13(18) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C7 C4 C5 C6 178.7(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
F1 C1 C6 C5 179.7(2) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C3 C4 C7 C8 -179.81(17) . . . . ?
C5 C4 C7 C8 0.5(3) . . . . ?
C4 C7 C8 C9 -179.13(15) . . . . ?
C4 C7 C8 C11 2.0(3) . . . . ?
C7 C8 C9 O2 -173.48(16) . . . . ?
C11 C8 C9 O2 5.5(2) . . . . ?
C7 C8 C9 C10 7.3(3) . . . . ?
C11 C8 C9 C10 -173.72(17) . . . . ?
C7 C8 C11 O1 79.6(2) . . . . ?
C9 C8 C11 O1 -99.31(17) . . . . ?
C7 C8 C11 C12 -102.41(17) . . . . ?
C9 C8 C11 C12 78.64(17) . . . . ?
O1 C11 C12 C17 -167.28(15) . . . . ?
C8 C11 C12 C17 14.8(2) . . . . ?
O1 C11 C12 C13 13.4(2) . . . . ?
C8 C11 C12 C13 -164.53(15) . . . . ?
C17 C12 C13 C14 -1.2(3) . . . . ?
C11 C12 C13 C14 178.18(18) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C12 0.1(3) . . . . ?
C13 C12 C17 C16 0.6(2) . . . . ?
C11 C12 C17 C16 -178.77(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.029




data_e:\111123c\work\mo_111123c_0m
_database_code_depnum_ccdc_archive 'CCDC 885165'
#TrackingRef 'web_deposit_cif_file_0_YanYang_1338738925.(E)-2-(2-(iodomethyl)-1,3-dioxolan-2-yl)-1,3-diphenylprop-2-en-1-one.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 I O3'
_chemical_formula_weight         420.23

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'
I I -0.4742 1.8119 '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)/m


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

_cell_length_a                   11.8628(12)
_cell_length_b                   5.9193(6)
_cell_length_c                   12.0256(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.1910(10)
_cell_angle_gamma                90.00
_cell_volume                     839.51(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    6314
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      32.09

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    1.919
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7617
_exptl_absorpt_correction_T_max  0.8312
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7647
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4636
_reflns_number_gt                4502
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0473P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0107(15)
_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   0.027(16)
_refine_ls_number_reflns         4636
_refine_ls_number_parameters     228
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_restrained_S_all      1.213
_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
C1 C 0.1379(2) 0.4836(4) 0.17061(19) 0.0238(4) Uani 1 1 d . . .
C2 C 0.0619(2) 0.6511(4) 0.1920(2) 0.0272(4) Uani 1 1 d . . .
H2 H 0.0889 0.7915 0.2200 0.033 Uiso 1 1 calc R . .
C3 C -0.0542(2) 0.6133(5) 0.1725(2) 0.0321(5) Uani 1 1 d . . .
H3 H -0.1054 0.7259 0.1897 0.038 Uiso 1 1 calc R . .
C4 C -0.0947(2) 0.4071(6) 0.1269(2) 0.0355(5) Uani 1 1 d . . .
H4 H -0.1732 0.3820 0.1127 0.043 Uiso 1 1 calc R . .
C5 C -0.0197(3) 0.2416(5) 0.1030(2) 0.0353(6) Uani 1 1 d . . .
H5 H -0.0467 0.1033 0.0723 0.042 Uiso 1 1 calc R . .
C6 C 0.0956(2) 0.2793(4) 0.1244(2) 0.0302(5) Uani 1 1 d . . .
H6 H 0.1465 0.1657 0.1077 0.036 Uiso 1 1 calc R . .
C7 C 0.26202(19) 0.5138(4) 0.18614(19) 0.0235(4) Uani 1 1 d . . .
H7 H 0.3032 0.4104 0.1471 0.028 Uiso 1 1 calc R . .
C8 C 0.32556(18) 0.6676(4) 0.24797(19) 0.0222(4) Uani 1 1 d . . .
C9 C 0.28043(17) 0.8440(4) 0.32070(19) 0.0227(4) Uani 1 1 d . . .
C10 C 0.22332(19) 0.7717(4) 0.4191(2) 0.0240(4) Uani 1 1 d . . .
C11 C 0.1536(2) 0.9256(4) 0.4661(2) 0.0328(5) Uani 1 1 d . . .
H11 H 0.1404 1.0687 0.4333 0.039 Uiso 1 1 calc R . .
C12 C 0.1034(2) 0.8683(7) 0.5616(2) 0.0428(6) Uani 1 1 d . . .
H12 H 0.0556 0.9718 0.5929 0.051 Uiso 1 1 calc R . .
C13 C 0.1236(3) 0.6605(7) 0.6100(2) 0.0457(7) Uani 1 1 d . . .
H13 H 0.0910 0.6241 0.6756 0.055 Uiso 1 1 calc R . .
C14 C 0.1912(3) 0.5037(5) 0.5639(2) 0.0427(7) Uani 1 1 d . . .
H14 H 0.2038 0.3612 0.5974 0.051 Uiso 1 1 calc R . .
C15 C 0.2403(2) 0.5583(4) 0.4675(2) 0.0310(5) Uani 1 1 d . . .
H15 H 0.2851 0.4513 0.4348 0.037 Uiso 1 1 calc R . .
C16 C 0.45335(18) 0.6828(4) 0.23777(19) 0.0237(4) Uani 1 1 d . A .
C17 C 0.5496(6) 0.5636(10) 0.4048(6) 0.0286(14) Uani 0.57 1 d PDU A 1
H17A H 0.4957 0.5191 0.4572 0.034 Uiso 0.57 1 calc PR A 1
H17B H 0.6238 0.5918 0.4467 0.034 Uiso 0.57 1 calc PR A 1
C18 C 0.5575(7) 0.3869(18) 0.3171(6) 0.0441(19) Uani 0.57 1 d PDU A 1
H18A H 0.6371 0.3574 0.3072 0.053 Uiso 0.57 1 calc PR A 1
H18B H 0.5230 0.2457 0.3392 0.053 Uiso 0.57 1 calc PR A 1
C17' C 0.5746(10) 0.5667(18) 0.3849(11) 0.045(3) Uani 0.43 1 d PDU A 2
H17C H 0.5685 0.5490 0.4651 0.054 Uiso 0.43 1 calc PR A 2
H17D H 0.6548 0.5856 0.3741 0.054 Uiso 0.43 1 calc PR A 2
C18' C 0.5256(7) 0.363(2) 0.3211(7) 0.0299(19) Uani 0.43 1 d PDU A 2
H18C H 0.5816 0.2420 0.3177 0.036 Uiso 0.43 1 calc PR A 2
H18D H 0.4582 0.3038 0.3517 0.036 Uiso 0.43 1 calc PR A 2
C19 C 0.46996(18) 0.8492(5) 0.1453(2) 0.0295(5) Uani 1 1 d . . .
H19A H 0.4401 0.9968 0.1646 0.035 Uiso 1 1 calc R . .
H19B H 0.4266 0.7981 0.0759 0.035 Uiso 1 1 calc R . .
I1 I 0.645021(11) 0.88560(5) 0.117987(13) 0.04476(8) Uani 1 1 d . . .
O1 O 0.29358(17) 1.0433(3) 0.30170(18) 0.0338(4) Uani 1 1 d . . .
O2 O 0.51029(16) 0.7577(3) 0.34171(15) 0.0286(4) Uani 1 1 d D . .
O3 O 0.49844(16) 0.4707(3) 0.21532(16) 0.0302(4) Uani 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0254(10) 0.0246(9) 0.0210(10) 0.0020(8) 0.0009(8) -0.0026(8)
C2 0.0264(10) 0.0279(10) 0.0267(11) -0.0018(8) -0.0004(8) -0.0001(8)
C3 0.0227(10) 0.0411(13) 0.0324(12) 0.0028(10) 0.0033(9) 0.0026(9)
C4 0.0269(9) 0.0438(15) 0.0345(11) 0.0049(12) -0.0022(8) -0.0056(11)
C5 0.0408(14) 0.0312(12) 0.0322(13) 0.0025(9) -0.0041(10) -0.0108(10)
C6 0.0385(14) 0.0283(11) 0.0229(11) -0.0009(8) -0.0003(9) -0.0021(9)
C7 0.0250(10) 0.0234(10) 0.0221(10) -0.0017(7) 0.0027(7) 0.0003(7)
C8 0.0212(9) 0.0216(9) 0.0236(9) 0.0019(7) 0.0018(7) 0.0018(7)
C9 0.0181(8) 0.0235(11) 0.0266(9) -0.0008(7) 0.0032(7) 0.0030(7)
C10 0.0201(9) 0.0273(10) 0.0247(10) -0.0058(8) 0.0026(8) -0.0015(8)
C11 0.0338(11) 0.0298(14) 0.0351(12) -0.0082(9) 0.0052(9) 0.0038(8)
C12 0.0396(12) 0.0522(16) 0.0389(13) -0.0166(15) 0.0149(10) 0.0026(15)
C13 0.0550(17) 0.0574(19) 0.0273(14) -0.0088(12) 0.0157(12) -0.0138(15)
C14 0.065(2) 0.0373(15) 0.0280(13) 0.0017(11) 0.0135(13) -0.0069(13)
C15 0.0369(12) 0.0302(11) 0.0273(11) -0.0011(9) 0.0097(9) 0.0005(9)
C16 0.0199(9) 0.0258(10) 0.0251(10) 0.0001(8) 0.0008(7) 0.0028(7)
C17 0.031(3) 0.033(2) 0.021(3) 0.0067(17) -0.005(2) 0.0001(19)
C18 0.048(4) 0.033(3) 0.049(3) 0.007(3) -0.004(3) 0.013(4)
C17' 0.040(5) 0.053(5) 0.043(6) 0.010(4) 0.011(4) 0.004(4)
C18' 0.020(3) 0.026(4) 0.044(3) 0.007(3) 0.004(2) 0.001(3)
C19 0.0201(8) 0.0409(15) 0.0280(10) 0.0085(9) 0.0043(7) 0.0019(9)
I1 0.02562(9) 0.06916(14) 0.04129(11) 0.01005(10) 0.01170(6) -0.00109(9)
O1 0.0336(9) 0.0230(8) 0.0465(11) 0.0020(7) 0.0122(8) 0.0009(7)
O2 0.0290(8) 0.0289(8) 0.0263(8) -0.0005(6) -0.0039(6) 0.0012(6)
O3 0.0262(8) 0.0305(8) 0.0338(9) -0.0044(7) 0.0029(7) 0.0083(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(3) . ?
C1 C6 1.401(3) . ?
C1 C7 1.475(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.401(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.352(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.498(3) . ?
C8 C16 1.537(3) . ?
C9 O1 1.215(3) . ?
C9 C10 1.488(3) . ?
C10 C11 1.391(3) . ?
C10 C15 1.396(4) . ?
C11 C12 1.392(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.371(6) . ?
C12 H12 0.9400 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.391(4) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 O3 1.402(3) . ?
C16 O2 1.426(3) . ?
C16 C19 1.514(3) . ?
C17 O2 1.427(5) . ?
C17 C18 1.495(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 O3 1.432(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C17' O2 1.430(7) . ?
C17' C18' 1.512(15) . ?
C17' H17C 0.9800 . ?
C17' H17D 0.9800 . ?
C18' O3 1.428(6) . ?
C18' H18C 0.9800 . ?
C18' H18D 0.9800 . ?
C19 I1 2.148(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 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
C2 C1 C6 118.6(2) . . ?
C2 C1 C7 123.5(2) . . ?
C6 C1 C7 117.7(2) . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C8 C7 C1 129.9(2) . . ?
C8 C7 H7 115.1 . . ?
C1 C7 H7 115.1 . . ?
C7 C8 C9 125.3(2) . . ?
C7 C8 C16 119.5(2) . . ?
C9 C8 C16 115.06(18) . . ?
O1 C9 C10 120.5(2) . . ?
O1 C9 C8 120.4(2) . . ?
C10 C9 C8 119.06(19) . . ?
C11 C10 C15 119.2(2) . . ?
C11 C10 C9 118.5(2) . . ?
C15 C10 C9 122.3(2) . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O3 C16 O2 107.01(18) . . ?
O3 C16 C19 111.0(2) . . ?
O2 C16 C19 110.76(19) . . ?
O3 C16 C8 111.28(19) . . ?
O2 C16 C8 109.05(18) . . ?
C19 C16 C8 107.73(17) . . ?
O2 C17 C18 103.3(5) . . ?
O2 C17 H17A 111.1 . . ?
C18 C17 H17A 111.1 . . ?
O2 C17 H17B 111.1 . . ?
C18 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
O3 C18 C17 107.4(6) . . ?
O3 C18 H18A 110.2 . . ?
C17 C18 H18A 110.2 . . ?
O3 C18 H18B 110.2 . . ?
C17 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
O2 C17' C18' 106.6(9) . . ?
O2 C17' H17C 110.4 . . ?
C18' C17' H17C 110.4 . . ?
O2 C17' H17D 110.4 . . ?
C18' C17' H17D 110.4 . . ?
H17C C17' H17D 108.6 . . ?
O3 C18' C17' 97.6(8) . . ?
O3 C18' H18C 112.2 . . ?
C17' C18' H18C 112.2 . . ?
O3 C18' H18D 112.2 . . ?
C17' C18' H18D 112.2 . . ?
H18C C18' H18D 109.8 . . ?
C16 C19 I1 112.48(14) . . ?
C16 C19 H19A 109.1 . . ?
I1 C19 H19A 109.1 . . ?
C16 C19 H19B 109.1 . . ?
I1 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C16 O2 C17 108.2(3) . . ?
C16 O2 C17' 104.9(6) . . ?
C17 O2 C17' 16.1(6) . . ?
C16 O3 C18' 106.4(5) . . ?
C16 O3 C18 107.9(5) . . ?
C18' O3 C18 16.6(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 2.7(4) . . . . ?
C7 C1 C2 C3 178.1(2) . . . . ?
C1 C2 C3 C4 -2.3(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
C7 C1 C6 C5 -177.3(2) . . . . ?
C2 C1 C7 C8 19.8(4) . . . . ?
C6 C1 C7 C8 -164.7(2) . . . . ?
C1 C7 C8 C9 2.4(4) . . . . ?
C1 C7 C8 C16 -171.9(2) . . . . ?
C7 C8 C9 O1 -118.2(3) . . . . ?
C16 C8 C9 O1 56.3(3) . . . . ?
C7 C8 C9 C10 64.1(3) . . . . ?
C16 C8 C9 C10 -121.4(2) . . . . ?
O1 C9 C10 C11 21.0(3) . . . . ?
C8 C9 C10 C11 -161.4(2) . . . . ?
O1 C9 C10 C15 -156.9(2) . . . . ?
C8 C9 C10 C15 20.7(3) . . . . ?
C15 C10 C11 C12 1.3(4) . . . . ?
C9 C10 C11 C12 -176.7(2) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 -1.6(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 C10 1.3(5) . . . . ?
C11 C10 C15 C14 -2.2(4) . . . . ?
C9 C10 C15 C14 175.6(3) . . . . ?
C7 C8 C16 O3 -32.4(3) . . . . ?
C9 C8 C16 O3 152.79(19) . . . . ?
C7 C8 C16 O2 -150.2(2) . . . . ?
C9 C8 C16 O2 35.0(2) . . . . ?
C7 C8 C16 C19 89.6(2) . . . . ?
C9 C8 C16 C19 -85.3(2) . . . . ?
O2 C17 C18 O3 -13.4(8) . . . . ?
O2 C17' C18' O3 35.3(9) . . . . ?
O3 C16 C19 I1 -56.8(2) . . . . ?
O2 C16 C19 I1 61.9(2) . . . . ?
C8 C16 C19 I1 -178.91(15) . . . . ?
O3 C16 O2 C17 -25.6(4) . . . . ?
C19 C16 O2 C17 -146.7(4) . . . . ?
C8 C16 O2 C17 94.9(4) . . . . ?
O3 C16 O2 C17' -9.1(6) . . . . ?
C19 C16 O2 C17' -130.2(5) . . . . ?
C8 C16 O2 C17' 111.4(5) . . . . ?
C18 C17 O2 C16 23.5(6) . . . . ?
C18 C17 O2 C17' -57(3) . . . . ?
C18' C17' O2 C16 -16.9(8) . . . . ?
C18' C17' O2 C17 87(3) . . . . ?
O2 C16 O3 C18' 33.5(4) . . . . ?
C19 C16 O3 C18' 154.5(4) . . . . ?
C8 C16 O3 C18' -85.5(4) . . . . ?
O2 C16 O3 C18 16.3(5) . . . . ?
C19 C16 O3 C18 137.2(4) . . . . ?
C8 C16 O3 C18 -102.8(4) . . . . ?
C17' C18' O3 C16 -41.1(6) . . . . ?
C17' C18' O3 C18 56(3) . . . . ?
C17 C18 O3 C16 -1.6(7) . . . . ?
C17 C18 O3 C18' -89(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.192