# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dias, Jerry'
_publ_contact_author_email       diasj@umkc.edu

_publ_section_title              
;
Synthesis and structural analysis
of a novel iodinated cyclopentadienone via ring-contraction
iodination and its application in synthesis
of alkyne-functionlized cyclopentadienones;

;
loop_
_publ_author_name
J.Dias
X.Chen
X.Bai
C.Barnes
Z.Peng
T.Sandreczki
E.Kadnikova

# Attachment '24ditertbutylcyclopentadienone5iodide.CIF'

data_tB2OHPhI2-m
_database_code_depnum_ccdc_archive 'CCDC 783904'
#TrackingRef '24ditertbutylcyclopentadienone5iodide.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H19 I O'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            red

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         318.18

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           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_int_tables_number      62
_chemical_absolute_configuration ?

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

_cell_length_a                   18.0985(17)
_cell_length_b                   8.0587(7)
_cell_length_c                   9.1236(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1330.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.6
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    2.382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.54
_exptl_absorpt_process_details   
;
Data were corrected for decay and absorption using the program SADABS
(Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
G\"ottingen, Germany).
;

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            14653
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1633
_reflns_number_gt                1594
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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^)+(0.0181P)^2^+0.6842P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0232(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1633
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0156
_refine_ls_R_factor_gt           0.0151
_refine_ls_wR_factor_ref         0.0381
_refine_ls_wR_factor_gt          0.0378
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.093703(6) 0.2500 0.977542(15) 0.02814(7) Uani 1 2 d S . .
O1 O -0.05005(8) 0.2500 0.75975(15) 0.0319(3) Uani 1 2 d S . .
C1 C -0.01871(10) 0.2500 1.01884(19) 0.0189(3) Uani 1 2 d S . .
C2 C -0.06917(10) 0.2500 0.8863(2) 0.0204(3) Uani 1 2 d S . .
C3 C -0.14727(10) 0.2500 0.94634(19) 0.0184(3) Uani 1 2 d S . .
C4 C -0.14024(9) 0.2500 1.0917(2) 0.0193(3) Uani 1 2 d S . .
H4 H -0.1810 0.2500 1.1574 0.023 Uiso 1 2 calc SR . .
C5 C -0.06025(9) 0.2500 1.14083(19) 0.0175(3) Uani 1 2 d S . .
C6 C -0.21549(9) 0.2500 0.85112(19) 0.0190(3) Uani 1 2 d S . .
C7 C -0.21564(8) 0.09448(18) 0.75348(16) 0.0299(3) Uani 1 1 d . . .
H7A H -0.2598 0.0950 0.6913 0.045 Uiso 1 1 calc R . .
H7B H -0.2158 -0.0050 0.8153 0.045 Uiso 1 1 calc R . .
H7C H -0.1714 0.0944 0.6916 0.045 Uiso 1 1 calc R . .
C8 C -0.28537(10) 0.2500 0.9458(2) 0.0252(4) Uani 1 2 d S . .
H8A H -0.3291 0.2500 0.8824 0.038 Uiso 1 2 calc SR . .
H8B H -0.2859 0.3493 1.0078 0.038 Uiso 0.50 1 calc PR . .
H8C H -0.2859 0.1507 1.0078 0.038 Uiso 0.50 1 calc PR . .
C9 C -0.04349(10) 0.2500 1.30364(19) 0.0196(3) Uani 1 2 d S . .
C10 C -0.07880(8) 0.09413(18) 1.37142(15) 0.0284(3) Uani 1 1 d . . .
H10A H -0.0686 0.0917 1.4769 0.043 Uiso 1 1 calc R . .
H10B H -0.0579 -0.0051 1.3252 0.043 Uiso 1 1 calc R . .
H10C H -0.1323 0.0966 1.3553 0.043 Uiso 1 1 calc R . .
C11 C 0.03892(10) 0.2500 1.3400(2) 0.0279(4) Uani 1 2 d S . .
H11A H 0.0454 0.2500 1.4466 0.042 Uiso 1 2 calc SR . .
H11B H 0.0621 0.3493 1.2984 0.042 Uiso 0.50 1 calc PR . .
H11C H 0.0621 0.1507 1.2984 0.042 Uiso 0.50 1 calc PR . .

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
I1 0.01541(9) 0.04209(10) 0.02691(10) 0.000 0.00157(4) 0.000
O1 0.0237(7) 0.0547(9) 0.0174(6) 0.000 0.0015(5) 0.000
C1 0.0146(8) 0.0223(8) 0.0199(8) 0.000 -0.0023(6) 0.000
C2 0.0196(8) 0.0227(8) 0.0189(8) 0.000 -0.0007(7) 0.000
C3 0.0178(8) 0.0185(8) 0.0190(8) 0.000 -0.0018(6) 0.000
C4 0.0155(7) 0.0219(8) 0.0204(8) 0.000 -0.0008(6) 0.000
C5 0.0167(8) 0.0177(7) 0.0181(8) 0.000 -0.0030(6) 0.000
C6 0.0168(8) 0.0220(8) 0.0182(8) 0.000 -0.0034(6) 0.000
C7 0.0250(6) 0.0341(7) 0.0305(7) -0.0112(6) -0.0081(5) 0.0029(6)
C8 0.0195(8) 0.0321(10) 0.0241(9) 0.000 -0.0021(7) 0.000
C9 0.0207(8) 0.0230(8) 0.0151(8) 0.000 -0.0026(6) 0.000
C10 0.0333(7) 0.0299(7) 0.0219(6) 0.0058(5) -0.0039(5) -0.0058(6)
C11 0.0222(9) 0.0397(11) 0.0219(9) 0.000 -0.0067(7) 0.000

_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
I1 C1 2.0691(18) . ?
O1 C2 1.205(2) . ?
C1 C5 1.343(2) . ?
C1 C2 1.516(2) . ?
C2 C3 1.516(2) . ?
C3 C4 1.332(3) . ?
C3 C6 1.510(2) . ?
C4 C5 1.515(2) . ?
C4 H4 0.9500 . ?
C5 C9 1.516(2) . ?
C6 C8 1.532(3) . ?
C6 C7 1.5376(16) . ?
C6 C7 1.5376(16) 8_565 ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.528(2) . ?
C9 C10 1.5390(17) 8_565 ?
C9 C10 1.5390(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C5 C1 C2 108.90(15) . . ?
C5 C1 I1 134.53(13) . . ?
C2 C1 I1 116.57(12) . . ?
O1 C2 C1 126.25(17) . . ?
O1 C2 C3 127.88(17) . . ?
C1 C2 C3 105.86(15) . . ?
C4 C3 C6 130.61(16) . . ?
C4 C3 C2 105.71(14) . . ?
C6 C3 C2 123.68(15) . . ?
C3 C4 C5 112.69(15) . . ?
C3 C4 H4 123.7 . . ?
C5 C4 H4 123.7 . . ?
C1 C5 C4 106.84(15) . . ?
C1 C5 C9 134.41(16) . . ?
C4 C5 C9 118.75(15) . . ?
C3 C6 C8 110.53(15) . . ?
C3 C6 C7 109.56(9) . . ?
C8 C6 C7 108.99(10) . . ?
C3 C6 C7 109.56(10) . 8_565 ?
C8 C6 C7 108.99(10) . 8_565 ?
C7 C6 C7 109.18(15) . 8_565 ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 C11 114.09(15) . . ?
C5 C9 C10 108.10(10) . 8_565 ?
C11 C9 C10 108.54(10) . 8_565 ?
C5 C9 C10 108.10(10) . . ?
C11 C9 C10 108.54(10) . . ?
C10 C9 C10 109.40(16) 8_565 . ?
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 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 O1 180.0 . . . . ?
I1 C1 C2 O1 0.0 . . . . ?
C5 C1 C2 C3 0.0 . . . . ?
I1 C1 C2 C3 180.0 . . . . ?
O1 C2 C3 C4 180.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
O1 C2 C3 C6 0.0 . . . . ?
C1 C2 C3 C6 180.0 . . . . ?
C6 C3 C4 C5 180.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C1 C5 C4 0.0 . . . . ?
I1 C1 C5 C4 180.0 . . . . ?
C2 C1 C5 C9 180.0 . . . . ?
I1 C1 C5 C9 0.0 . . . . ?
C3 C4 C5 C1 0.0 . . . . ?
C3 C4 C5 C9 180.0 . . . . ?
C4 C3 C6 C8 0.0 . . . . ?
C2 C3 C6 C8 180.0 . . . . ?
C4 C3 C6 C7 -120.12(10) . . . . ?
C2 C3 C6 C7 59.88(10) . . . . ?
C4 C3 C6 C7 120.12(10) . . . 8_565 ?
C2 C3 C6 C7 -59.88(10) . . . 8_565 ?
C1 C5 C9 C11 0.0 . . . . ?
C4 C5 C9 C11 180.0 . . . . ?
C1 C5 C9 C10 120.84(10) . . . 8_565 ?
C4 C5 C9 C10 -59.16(10) . . . 8_565 ?
C1 C5 C9 C10 -120.84(10) . . . . ?
C4 C5 C9 C10 59.16(10) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.077

# Attachment 'TB2AC.CIF'

data_tB2AcPhI-m
_database_code_depnum_ccdc_archive 'CCDC 783905'
#TrackingRef 'TB2AC.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H25 I O4'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         432.28

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   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?

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

_cell_length_a                   25.726(5)
_cell_length_b                   9.7110(17)
_cell_length_c                   18.526(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.523(2)
_cell_angle_gamma                90.00
_cell_volume                     3766.9(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9863
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      28.5
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    1.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_process_details   
;
Data were corrected for decay and absorption using the program SADABS
(Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
G\"ottingen, Germany).
;

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            21540
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.69
_reflns_number_total             4586
_reflns_number_gt                4228
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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^)+(0.0270P)^2^+4.4593P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4586
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0560
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
I1 I 0.280530(5) 0.205028(11) 0.163166(8) 0.03194(5) Uani 1 1 d . . .
O1 O 0.39116(5) -0.00614(12) 0.29602(7) 0.0225(2) Uani 1 1 d . . .
C1 C 0.22358(7) -0.22564(15) 0.10833(9) 0.0165(3) Uani 1 1 d . . .
O2 O 0.41486(6) 0.04871(14) 0.19956(8) 0.0336(3) Uani 1 1 d . . .
C2 C 0.27991(7) -0.29149(15) 0.17509(10) 0.0182(3) Uani 1 1 d . . .
H2 H 0.2791 -0.3890 0.1783 0.022 Uiso 1 1 calc R . .
O3 O 0.17213(5) -0.00666(12) 0.04215(7) 0.0208(2) Uani 1 1 d . . .
C3 C 0.33734(7) -0.22482(15) 0.23747(9) 0.0179(3) Uani 1 1 d . . .
O4 O 0.20717(6) 0.01840(14) -0.04428(8) 0.0327(3) Uani 1 1 d . . .
C4 C 0.33700(7) -0.08150(16) 0.23131(9) 0.0186(3) Uani 1 1 d . . .
C5 C 0.28229(7) -0.01011(16) 0.16684(9) 0.0193(3) Uani 1 1 d . . .
C6 C 0.22673(7) -0.08283(16) 0.10476(9) 0.0180(3) Uani 1 1 d . . .
C7 C 0.16218(7) -0.30864(16) 0.04441(10) 0.0194(3) Uani 1 1 d . . .
C8 C 0.17155(8) -0.46267(17) 0.06739(12) 0.0278(3) Uani 1 1 d . . .
H8A H 0.1848 -0.4751 0.1284 0.042 Uiso 1 1 calc R . .
H8B H 0.2046 -0.4996 0.0619 0.042 Uiso 1 1 calc R . .
H8C H 0.1313 -0.5116 0.0266 0.042 Uiso 1 1 calc R . .
C9 C 0.14197(9) -0.29502(19) -0.05136(11) 0.0303(4) Uani 1 1 d . . .
H9A H 0.1060 -0.3568 -0.0900 0.045 Uiso 1 1 calc R . .
H9B H 0.1779 -0.3198 -0.0536 0.045 Uiso 1 1 calc R . .
H9C H 0.1291 -0.1998 -0.0715 0.045 Uiso 1 1 calc R . .
C10 C 0.10820(7) -0.25788(19) 0.05072(11) 0.0268(3) Uani 1 1 d . . .
H10A H 0.1221 -0.2644 0.1123 0.040 Uiso 1 1 calc R . .
H10B H 0.0702 -0.3151 0.0129 0.040 Uiso 1 1 calc R . .
H10C H 0.0980 -0.1619 0.0310 0.040 Uiso 1 1 calc R . .
C11 C 0.39639(7) -0.30744(17) 0.30926(10) 0.0224(3) Uani 1 1 d . . .
C12 C 0.38221(9) -0.46243(19) 0.30051(13) 0.0344(4) Uani 1 1 d . . .
H12A H 0.4205 -0.5120 0.3472 0.052 Uiso 1 1 calc R . .
H12B H 0.3698 -0.4945 0.2424 0.052 Uiso 1 1 calc R . .
H12C H 0.3473 -0.4797 0.3063 0.052 Uiso 1 1 calc R . .
C13 C 0.45228(8) -0.28682(19) 0.30125(12) 0.0301(4) Uani 1 1 d . . .
H13A H 0.4654 -0.1900 0.3123 0.045 Uiso 1 1 calc R . .
H13B H 0.4386 -0.3125 0.2415 0.045 Uiso 1 1 calc R . .
H13C H 0.4883 -0.3449 0.3449 0.045 Uiso 1 1 calc R . .
C14 C 0.41650(8) -0.2635(2) 0.40193(11) 0.0315(4) Uani 1 1 d . . .
H14A H 0.4293 -0.1665 0.4118 0.047 Uiso 1 1 calc R . .
H14B H 0.4525 -0.3203 0.4470 0.047 Uiso 1 1 calc R . .
H14C H 0.3805 -0.2759 0.4061 0.047 Uiso 1 1 calc R . .
C15 C 0.42654(7) 0.05682(17) 0.27180(11) 0.0258(3) Uani 1 1 d . . .
C16 C 0.48070(9) 0.1352(2) 0.34880(14) 0.0412(5) Uani 1 1 d . . .
H16A H 0.5175 0.1336 0.3459 0.062 Uiso 1 1 calc R . .
H16B H 0.4924 0.0925 0.4043 0.062 Uiso 1 1 calc R . .
H16C H 0.4676 0.2307 0.3466 0.062 Uiso 1 1 calc R . .
C17 C 0.16887(8) 0.04352(17) -0.02967(10) 0.0252(3) Uani 1 1 d . . .
C18 C 0.11050(10) 0.1310(2) -0.08519(13) 0.0413(5) Uani 1 1 d . . .
H18A H 0.1206 0.2262 -0.0638 0.062 Uiso 1 1 calc R . .
H18B H 0.0766 0.0961 -0.0810 0.062 Uiso 1 1 calc R . .
H18C H 0.0961 0.1279 -0.1471 0.062 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.03117(7) 0.01519(7) 0.04442(8) -0.00088(4) 0.01909(6) -0.00116(4)
O1 0.0185(5) 0.0248(6) 0.0228(5) -0.0065(4) 0.0113(4) -0.0069(4)
C1 0.0157(6) 0.0177(7) 0.0178(6) -0.0009(5) 0.0107(5) -0.0018(5)
O2 0.0348(7) 0.0383(7) 0.0362(7) -0.0080(5) 0.0253(6) -0.0124(6)
C2 0.0182(7) 0.0160(7) 0.0206(7) 0.0008(5) 0.0113(6) -0.0006(5)
O3 0.0182(5) 0.0219(5) 0.0222(5) 0.0053(4) 0.0116(4) 0.0052(4)
C3 0.0167(6) 0.0198(7) 0.0179(6) 0.0019(5) 0.0104(5) 0.0012(5)
O4 0.0358(6) 0.0360(7) 0.0367(6) 0.0109(5) 0.0270(6) 0.0094(5)
C4 0.0164(6) 0.0204(7) 0.0197(6) -0.0035(5) 0.0108(6) -0.0044(5)
C5 0.0208(7) 0.0151(7) 0.0243(7) -0.0001(5) 0.0145(6) -0.0009(5)
C6 0.0156(6) 0.0197(7) 0.0190(6) 0.0029(5) 0.0103(5) 0.0024(5)
C7 0.0151(6) 0.0218(7) 0.0199(7) -0.0014(5) 0.0093(6) -0.0025(5)
C8 0.0224(7) 0.0212(8) 0.0358(9) -0.0019(6) 0.0146(7) -0.0056(6)
C9 0.0322(9) 0.0359(10) 0.0202(7) -0.0060(6) 0.0138(7) -0.0073(7)
C10 0.0180(7) 0.0317(9) 0.0314(8) -0.0024(7) 0.0147(6) -0.0024(6)
C11 0.0168(7) 0.0265(8) 0.0194(7) 0.0032(6) 0.0079(6) 0.0022(6)
C12 0.0284(8) 0.0245(9) 0.0358(9) 0.0083(7) 0.0104(7) 0.0050(7)
C13 0.0200(7) 0.0399(10) 0.0298(8) 0.0062(7) 0.0142(7) 0.0073(7)
C14 0.0269(8) 0.0433(10) 0.0195(7) 0.0045(7) 0.0108(7) 0.0042(7)
C15 0.0211(7) 0.0236(8) 0.0348(8) -0.0082(6) 0.0175(7) -0.0064(6)
C16 0.0299(9) 0.0485(12) 0.0505(11) -0.0279(10) 0.0263(9) -0.0220(9)
C17 0.0271(8) 0.0237(8) 0.0242(7) 0.0061(6) 0.0145(6) 0.0045(6)
C18 0.0406(10) 0.0476(12) 0.0372(10) 0.0220(9) 0.0234(9) 0.0238(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C5 2.0900(16) . ?
O1 C15 1.3704(19) . ?
O1 C4 1.4047(17) . ?
C1 C6 1.393(2) . ?
C1 C2 1.399(2) . ?
C1 C7 1.5405(19) . ?
O2 C15 1.192(2) . ?
C2 C3 1.398(2) . ?
C2 H2 0.9500 . ?
O3 C17 1.3732(19) . ?
O3 C6 1.4044(17) . ?
C3 C4 1.396(2) . ?
C3 C11 1.540(2) . ?
O4 C17 1.189(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.398(2) . ?
C7 C8 1.535(2) . ?
C7 C9 1.538(2) . ?
C7 C10 1.541(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.535(2) . ?
C11 C14 1.538(2) . ?
C11 C13 1.542(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.499(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.497(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C15 O1 C4 118.11(12) . . ?
C6 C1 C2 115.99(13) . . ?
C6 C1 C7 123.12(13) . . ?
C2 C1 C7 120.89(13) . . ?
C3 C2 C1 125.02(14) . . ?
C3 C2 H2 117.5 . . ?
C1 C2 H2 117.5 . . ?
C17 O3 C6 117.12(11) . . ?
C4 C3 C2 116.15(13) . . ?
C4 C3 C11 123.10(13) . . ?
C2 C3 C11 120.74(13) . . ?
C5 C4 C3 121.48(14) . . ?
C5 C4 O1 118.70(13) . . ?
C3 C4 O1 119.58(13) . . ?
C4 C5 C6 119.70(14) . . ?
C4 C5 I1 121.21(11) . . ?
C6 C5 I1 119.06(11) . . ?
C1 C6 C5 121.59(13) . . ?
C1 C6 O3 120.37(13) . . ?
C5 C6 O3 117.86(13) . . ?
C8 C7 C9 107.29(13) . . ?
C8 C7 C1 111.77(12) . . ?
C9 C7 C1 110.50(12) . . ?
C8 C7 C10 107.09(13) . . ?
C9 C7 C10 110.16(13) . . ?
C1 C7 C10 109.95(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C14 107.15(15) . . ?
C12 C11 C3 111.41(13) . . ?
C14 C11 C3 110.05(13) . . ?
C12 C11 C13 107.15(14) . . ?
C14 C11 C13 110.11(14) . . ?
C3 C11 C13 110.88(13) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 O1 123.79(14) . . ?
O2 C15 C16 126.21(16) . . ?
O1 C15 C16 109.99(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O3 123.77(14) . . ?
O4 C17 C18 126.40(15) . . ?
O3 C17 C18 109.83(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(2) . . . . ?
C7 C1 C2 C3 -178.24(14) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C2 C3 C11 179.06(14) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C11 C3 C4 C5 -178.45(13) . . . . ?
C2 C3 C4 O1 174.69(12) . . . . ?
C11 C3 C4 O1 -4.1(2) . . . . ?
C15 O1 C4 C5 -75.27(17) . . . . ?
C15 O1 C4 C3 110.22(16) . . . . ?
C3 C4 C5 C6 -2.1(2) . . . . ?
O1 C4 C5 C6 -176.46(13) . . . . ?
C3 C4 C5 I1 176.02(11) . . . . ?
O1 C4 C5 I1 1.62(18) . . . . ?
C2 C1 C6 C5 -2.6(2) . . . . ?
C7 C1 C6 C5 176.46(13) . . . . ?
C2 C1 C6 O3 -177.72(12) . . . . ?
C7 C1 C6 O3 1.4(2) . . . . ?
C4 C5 C6 C1 3.3(2) . . . . ?
I1 C5 C6 C1 -174.83(11) . . . . ?
C4 C5 C6 O3 178.48(13) . . . . ?
I1 C5 C6 O3 0.36(17) . . . . ?
C17 O3 C6 C1 -104.81(16) . . . . ?
C17 O3 C6 C5 79.93(17) . . . . ?
C6 C1 C7 C8 -176.42(14) . . . . ?
C2 C1 C7 C8 2.64(19) . . . . ?
C6 C1 C7 C9 64.17(19) . . . . ?
C2 C1 C7 C9 -116.76(15) . . . . ?
C6 C1 C7 C10 -57.64(19) . . . . ?
C2 C1 C7 C10 121.42(15) . . . . ?
C4 C3 C11 C12 178.97(15) . . . . ?
C2 C3 C11 C12 0.2(2) . . . . ?
C4 C3 C11 C14 60.27(19) . . . . ?
C2 C3 C11 C14 -118.46(16) . . . . ?
C4 C3 C11 C13 -61.79(19) . . . . ?
C2 C3 C11 C13 119.48(16) . . . . ?
C4 O1 C15 O2 -1.8(2) . . . . ?
C4 O1 C15 C16 178.19(15) . . . . ?
C6 O3 C17 O4 5.2(2) . . . . ?
C6 O3 C17 C18 -175.45(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        28.69
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.072