# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Chunling Fu'
_publ_contact_author_address     
;
Laboratory of Molecular Recognition and Synthesis
Zhejiang University
Department of Chemistry
Hanzhou
Zhejiang
310027
CHINA
;

_publ_section_title              
;
Efficient Two-step Synthesis of 3-Halo-3-enals or
2-Halo-2-alkenyl Ketones from Propargylic Bromides via a unique cationc
1,2-Aryl or Proton Shift in Electrophilic Addition Reaction of
2,3-Allenols with X+
;
loop_
_publ_author_name
'Chunling Fu.'
'Shengming Ma.'
'Jing Li.'
_publ_contact_author_email       masm@mail.sioc.ac.cn

data_fu-6-18-B
_database_code_depnum_ccdc_archive 'CCDC 259342'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C15 H17 I O3 '
_chemical_formula_moiety         'C15 H17 I O3 '
_chemical_formula_weight         372.20
_chemical_melting_point          ?

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z

#------------------------------------------------------------------------------

_cell_length_a                   9.8575(3)
_cell_length_b                   10.7013(4)
_cell_length_c                   14.9705(6)
_cell_angle_alpha                80.8520(8)
_cell_angle_beta                 75.931(3)
_cell_angle_gamma                89.9530(6)
_cell_volume                     1511.17(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4919
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.4
_cell_measurement_temperature    253(1)

#------------------------------------------------------------------------------

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736.00
_exptl_absorpt_coefficient_mu    2.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_T_max  0.792

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            13610
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_theta_max         27.45
_diffrn_measured_fraction_theta_max 0.9302
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.9469
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
Refinement using reflections with F^2^ > 2.0 sigma(F^2^).
The weighted R-factor (wR) and goodness of fit (S) are based on F^2^.
R-factor (gt) are based on F. The threshold expression of
F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt).
;
_reflns_number_total             6414
_reflns_number_gt                3907
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0610
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3885
_refine_ls_number_parameters     343
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[0.0004Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_shift/su_max          0.0000
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.474 1.812
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================

# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.79173(2) 0.09294(2) 0.07799(2) 0.05396(8) Uani 1.00 1 d . . .
I2 I 0.70484(3) 0.40254(2) 0.92515(2) 0.05926(9) Uani 1.00 1 d . . .
O11 O 0.3122(2) -0.1052(2) 0.4560(2) 0.0439(7) Uani 1.00 1 d . . .
O12 O 0.3377(2) 0.0956(2) 0.3675(2) 0.0537(7) Uani 1.00 1 d . . .
O21 O 1.1627(2) 0.5326(2) 0.6333(2) 0.0548(8) Uani 1.00 1 d . . .
O22 O 1.1855(2) 0.3735(2) 0.5433(2) 0.0427(7) Uani 1.00 1 d . . .
O13 O 0.9736(2) 0.1435(2) 0.3835(2) 0.0530(8) Uani 1.00 1 d . . .
O23 O 0.5236(2) 0.5893(2) 0.6195(2) 0.0559(8) Uani 1.00 1 d . . .
C1 C 0.8593(3) 0.0878(3) 0.2687(2) 0.0322(8) Uani 1.00 1 d . . .
C2 C 0.7126(3) 0.0260(3) 0.3174(2) 0.0308(8) Uani 1.00 1 d . . .
C3 C 0.6958(3) -0.0944(3) 0.3705(2) 0.0360(9) Uani 1.00 1 d . . .
C4 C 0.5640(3) -0.1473(3) 0.4204(2) 0.0379(9) Uani 1.00 1 d . . .
C5 C 0.4514(3) -0.0756(3) 0.4138(2) 0.0325(8) Uani 1.00 1 d . . .
C6 C 0.2385(3) 0.0027(3) 0.4262(3) 0.045(1) Uani 1.00 1 d . . .
C7 C 0.4669(3) 0.0435(3) 0.3622(2) 0.038(1) Uani 1.00 1 d . . .
C8 C 0.5946(3) 0.0980(3) 0.3144(2) 0.0372(9) Uani 1.00 1 d . . .
C9 C 0.8862(3) 0.1656(3) 0.3414(2) 0.0373(9) Uani 1.00 1 d . . .
C10 C 0.8552(3) 0.1776(3) 0.1803(2) 0.0351(9) Uani 1.00 1 d . . .
C11 C 0.8885(4) 0.2995(3) 0.1601(3) 0.056(1) Uani 1.00 1 d . . .
C12 C 0.9732(3) -0.0097(3) 0.2481(2) 0.0358(9) Uani 1.00 1 d . . .
C13 C 1.1163(3) 0.0452(3) 0.1912(2) 0.042(1) Uani 1.00 1 d . . .
C14 C 1.2229(3) -0.0569(3) 0.1772(3) 0.047(1) Uani 1.00 1 d . . .
C15 C 1.3674(4) -0.0050(4) 0.1202(3) 0.066(1) Uani 1.00 1 d . . .
C33 C 0.3846(3) 0.4074(3) 0.8143(3) 0.046(1) Uani 1.00 1 d . . .
C32 C 0.5265(3) 0.3776(3) 0.7563(2) 0.0388(9) Uani 1.00 1 d . . .
C34 C 0.2814(4) 0.2947(4) 0.8393(3) 0.069(1) Uani 1.00 1 d . . .
C35 C 0.1398(4) 0.3205(4) 0.8970(4) 0.098(2) Uani 1.00 1 d . . .
C21 C 0.6409(3) 0.4848(3) 0.7335(2) 0.0328(8) Uani 1.00 1 d . . .
C22 C 0.7867(3) 0.4434(3) 0.6839(2) 0.0319(8) Uani 1.00 1 d . . .
C23 C 0.8013(3) 0.3499(3) 0.6291(2) 0.0352(9) Uani 1.00 1 d . . .
C24 C 0.9326(3) 0.3185(3) 0.5780(2) 0.0379(9) Uani 1.00 1 d . . .
C25 C 1.0463(3) 0.3850(3) 0.5857(2) 0.0331(8) Uani 1.00 1 d . . .
C26 C 1.2607(3) 0.4626(3) 0.5772(3) 0.050(1) Uani 1.00 1 d . . .
C27 C 1.0325(3) 0.4791(3) 0.6394(2) 0.039(1) Uani 1.00 1 d . . .
C28 C 0.9061(3) 0.5132(3) 0.6873(2) 0.0386(9) Uani 1.00 1 d . . .
C29 C 0.6128(3) 0.5928(3) 0.6610(2) 0.0392(9) Uani 1.00 1 d . . .
C30 C 0.6475(3) 0.5358(3) 0.8216(2) 0.0374(9) Uani 1.00 1 d . . .
C31 C 0.6199(4) 0.6507(3) 0.8389(3) 0.054(1) Uani 1.00 1 d . . .
H3 H 0.7771 -0.1428 0.3733 0.044 Uiso 1.00 1 c R . .
H4 H 0.5535 -0.2302 0.4575 0.045 Uiso 1.00 1 c R . .
H61 H 0.1869 0.0367 0.4794 0.053 Uiso 1.00 1 c R . .
H8 H 0.6034 0.1824 0.2798 0.044 Uiso 1.00 1 c R . .
H9 H 0.8293 0.2369 0.3529 0.043 Uiso 1.00 1 c R . .
H121 H 0.9415 -0.0687 0.2148 0.043 Uiso 1.00 1 c R . .
H122 H 0.9846 -0.0538 0.3068 0.043 Uiso 1.00 1 c R . .
H131 H 1.1484 0.1061 0.2229 0.049 Uiso 1.00 1 c R . .
H132 H 1.1073 0.0864 0.1312 0.049 Uiso 1.00 1 c R . .
H141 H 1.1903 -0.1172 0.1453 0.055 Uiso 1.00 1 c R . .
H142 H 1.2305 -0.0983 0.2375 0.055 Uiso 1.00 1 c R . .
H28 H 0.8983 0.5810 0.7229 0.048 Uiso 1.00 1 c R . .
H62 H 0.1750 -0.0220 0.3920 0.053 Uiso 1.00 1 c R . .
H24 H 0.9421 0.2534 0.5398 0.046 Uiso 1.00 1 c R . .
H23 H 0.7191 0.3044 0.6260 0.043 Uiso 1.00 1 c R . .
H321 H 0.5595 0.3045 0.7896 0.046 Uiso 1.00 1 c R . .
H322 H 0.5140 0.3588 0.6982 0.046 Uiso 1.00 1 c R . .
H331 H 0.3473 0.4763 0.7794 0.054 Uiso 1.00 1 c R . .
H332 H 0.3968 0.4319 0.8709 0.054 Uiso 1.00 1 c R . .
H29 H 0.6708 0.6688 0.6477 0.046 Uiso 1.00 1 c R . .
H151 H 1.4208 0.0165 0.1618 0.078 Uiso 1.00 1 c R . .
H152 H 1.4140 -0.0684 0.0865 0.078 Uiso 1.00 1 c R . .
H153 H 1.3574 0.0695 0.0775 0.077 Uiso 1.00 1 c R . .
H341 H 0.3196 0.2260 0.8739 0.078 Uiso 1.00 1 c R . .
H342 H 0.2700 0.2705 0.7824 0.078 Uiso 1.00 1 c R . .
H351 H 0.0814 0.3518 0.8562 0.109 Uiso 1.00 1 c R . .
H352 H 0.0984 0.2434 0.9361 0.109 Uiso 1.00 1 c R . .
H353 H 0.1509 0.3834 0.9342 0.109 Uiso 1.00 1 c R . .
H262 H 1.3196 0.4184 0.6132 0.061 Uiso 1.00 1 c R . .
H261 H 1.3174 0.5191 0.5253 0.061 Uiso 1.00 1 c R . .
H311 H 0.6254 0.6758 0.8974 0.067 Uiso 1.00 1 d R . .
H312 H 0.5890 0.7144 0.7925 0.067 Uiso 1.00 1 d R . .
H111 H 0.9189 0.3376 0.2066 0.067 Uiso 1.00 1 d R . .
H112 H 0.8889 0.3427 0.1039 0.067 Uiso 1.00 1 d 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.0707(2) 0.0556(2) 0.0391(2) -0.0099(1) -0.0240(1) -0.0016(1)
I2 0.0766(2) 0.0663(2) 0.0389(2) 0.0171(1) -0.0228(1) -0.0070(1)
O11 0.037(1) 0.040(1) 0.051(2) -0.0032(9) -0.007(1) -0.003(1)
O12 0.032(1) 0.044(1) 0.077(2) 0.006(1) -0.011(1) 0.010(1)
O21 0.032(1) 0.061(2) 0.077(2) -0.000(1) -0.011(1) -0.036(1)
O22 0.036(1) 0.044(1) 0.048(2) 0.0053(9) -0.007(1) -0.015(1)
O13 0.046(1) 0.073(2) 0.050(2) 0.007(1) -0.021(1) -0.025(1)
O23 0.048(1) 0.064(2) 0.056(2) 0.002(1) -0.024(1) 0.007(1)
C1 0.035(2) 0.031(2) 0.032(2) 0.002(1) -0.013(1) -0.003(1)
C2 0.035(2) 0.029(2) 0.030(2) 0.002(1) -0.011(1) -0.006(1)
C3 0.039(2) 0.028(2) 0.042(2) 0.006(1) -0.015(1) -0.005(1)
C4 0.045(2) 0.024(2) 0.044(2) 0.002(1) -0.012(1) -0.001(1)
C5 0.035(2) 0.031(2) 0.031(2) -0.005(1) -0.007(1) -0.008(1)
C6 0.033(2) 0.052(2) 0.047(2) 0.001(1) -0.010(2) -0.002(2)
C7 0.034(2) 0.039(2) 0.043(2) 0.006(1) -0.014(2) -0.005(2)
C8 0.038(2) 0.027(2) 0.044(2) 0.002(1) -0.011(1) 0.003(1)
C9 0.039(2) 0.037(2) 0.033(2) 0.001(1) -0.005(1) -0.003(1)
C10 0.034(2) 0.035(2) 0.037(2) -0.002(1) -0.013(1) -0.003(1)
C11 0.073(2) 0.044(2) 0.052(2) -0.011(2) -0.027(2) 0.007(2)
C12 0.034(2) 0.036(2) 0.039(2) 0.004(1) -0.011(1) -0.007(1)
C13 0.036(2) 0.044(2) 0.043(2) 0.002(1) -0.008(1) -0.006(2)
C14 0.042(2) 0.051(2) 0.044(2) 0.009(1) -0.004(2) -0.010(2)
C15 0.043(2) 0.075(3) 0.075(3) 0.007(2) -0.001(2) -0.024(2)
C33 0.043(2) 0.043(2) 0.048(2) -0.006(1) -0.003(2) -0.008(2)
C32 0.039(2) 0.034(2) 0.041(2) -0.003(1) -0.006(1) -0.006(1)
C34 0.051(2) 0.057(2) 0.088(3) -0.016(2) 0.007(2) -0.014(2)
C35 0.051(2) 0.090(3) 0.131(5) -0.019(2) 0.025(3) -0.023(3)
C21 0.034(2) 0.028(2) 0.038(2) 0.000(1) -0.010(1) -0.007(1)
C22 0.033(2) 0.029(2) 0.034(2) 0.000(1) -0.010(1) -0.004(1)
C23 0.039(2) 0.030(2) 0.038(2) -0.003(1) -0.012(1) -0.005(1)
C24 0.047(2) 0.030(2) 0.039(2) 0.002(1) -0.010(1) -0.013(1)
C25 0.037(2) 0.028(2) 0.033(2) 0.007(1) -0.008(1) -0.003(1)
C26 0.039(2) 0.063(2) 0.052(2) 0.006(2) -0.011(2) -0.019(2)
C27 0.036(2) 0.042(2) 0.041(2) -0.001(1) -0.013(2) -0.007(2)
C28 0.040(2) 0.035(2) 0.046(2) 0.002(1) -0.012(1) -0.018(1)
C29 0.040(2) 0.037(2) 0.039(2) 0.004(1) -0.005(2) -0.007(1)
C30 0.037(2) 0.040(2) 0.035(2) 0.002(1) -0.008(1) -0.007(1)
C31 0.066(2) 0.045(2) 0.057(3) 0.013(2) -0.018(2) -0.024(2)

#==============================================================================

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SHELXS97
_computing_structure_refinement  CRYSTALS
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_molecular_graphics    ?

#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
I1 C10 2.113(4) ? . .
I2 C30 2.116(3) ? . .
O11 C5 1.378(3) ? . .
O11 C6 1.432(4) ? . .
O12 C6 1.422(3) ? . .
O12 C7 1.379(4) ? . .
O21 C26 1.415(4) ? . .
O21 C27 1.382(4) ? . .
O22 C25 1.379(3) ? . .
O22 C26 1.433(5) ? . .
O13 C9 1.188(4) ? . .
O23 C29 1.197(4) ? . .
C1 C2 1.548(4) ? . .
C1 C9 1.541(5) ? . .
C1 C10 1.515(4) ? . .
C1 C12 1.542(4) ? . .
C2 C3 1.389(4) ? . .
C2 C8 1.401(4) ? . .
C3 C4 1.400(4) ? . .
C4 C5 1.364(4) ? . .
C5 C7 1.369(4) ? . .
C7 C8 1.366(4) ? . .
C10 C11 1.316(4) ? . .
C12 C13 1.523(4) ? . .
C13 C14 1.519(4) ? . .
C14 C15 1.525(4) ? . .
C33 C32 1.519(4) ? . .
C33 C34 1.518(5) ? . .
C32 C21 1.547(4) ? . .
C34 C35 1.504(5) ? . .
C21 C22 1.549(4) ? . .
C21 C29 1.529(4) ? . .
C21 C30 1.520(5) ? . .
C22 C23 1.377(4) ? . .
C22 C28 1.410(4) ? . .
C23 C24 1.405(4) ? . .
C24 C25 1.366(4) ? . .
C25 C27 1.372(5) ? . .
C27 C28 1.359(4) ? . .
C30 C31 1.312(5) ? . .
C3 H3 0.9600 ? . .
C4 H4 0.9600 ? . .
C6 H61 0.9600 ? . .
C6 H62 0.9600 ? . .
C8 H8 0.9600 ? . .
C9 H9 0.9600 ? . .
C11 H111 0.9656 ? . .
C11 H112 0.8931 ? . .
C12 H121 0.9600 ? . .
C12 H122 0.9600 ? . .
C13 H131 0.9600 ? . .
C13 H132 0.9600 ? . .
C14 H141 0.9600 ? . .
C14 H142 0.9600 ? . .
C15 H151 0.9600 ? . .
C15 H152 0.9600 ? . .
C15 H153 0.9600 ? . .
C33 H331 0.9600 ? . .
C33 H332 0.9600 ? . .
C32 H321 0.9600 ? . .
C32 H322 0.9600 ? . .
C34 H341 0.9600 ? . .
C34 H342 0.9600 ? . .
C35 H351 0.9600 ? . .
C35 H352 0.9600 ? . .
C35 H353 0.9600 ? . .
C23 H23 0.9600 ? . .
C24 H24 0.9600 ? . .
C26 H262 0.9600 ? . .
C26 H261 0.9600 ? . .
C28 H28 0.9600 ? . .
C29 H29 0.9600 ? . .
C31 H311 0.9689 ? . .
C31 H312 0.9958 ? . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
I1 C10 C1 115.0(2) ? . . .
I1 C10 C11 117.3(3) ? . . .
I2 C30 C21 114.7(2) ? . . .
I2 C30 C31 118.6(3) ? . . .
O11 C5 C4 128.2(2) ? . . .
C6 O11 C5 105.4(2) ? . . .
O11 C5 C7 110.3(2) ? . . .
O11 C6 O12 108.5(2) ? . . .
C7 O12 C6 105.9(2) ? . . .
O12 C7 C5 109.9(2) ? . . .
O12 C7 C8 127.4(3) ? . . .
O21 C26 O22 108.5(2) ? . . .
C27 O21 C26 106.0(3) ? . . .
O21 C27 C25 109.8(2) ? . . .
O21 C27 C28 127.6(3) ? . . .
O22 C25 C24 128.3(3) ? . . .
C26 O22 C25 105.4(2) ? . . .
O22 C25 C27 110.1(3) ? . . .
O13 C9 C1 124.2(3) ? . . .
O23 C29 C21 124.6(3) ? . . .
C10 C1 C2 110.9(3) ? . . .
C12 C1 C2 113.2(2) ? . . .
C1 C2 C8 118.8(2) ? . . .
C9 C1 C2 101.9(2) ? . . .
C1 C2 C3 121.7(3) ? . . .
C10 C1 C9 108.9(2) ? . . .
C12 C1 C9 110.9(3) ? . . .
C1 C10 C11 127.7(3) ? . . .
C12 C1 C10 110.7(2) ? . . .
C1 C12 C13 115.4(2) ? . . .
C2 C3 C4 122.1(3) ? . . .
C8 C2 C3 119.3(2) ? . . .
C2 C8 C7 117.5(3) ? . . .
C3 C4 C5 116.9(3) ? . . .
C4 C5 C7 121.4(3) ? . . .
C5 C7 C8 122.7(3) ? . . .
C12 C13 C14 111.7(2) ? . . .
C13 C14 C15 113.0(3) ? . . .
C33 C32 C21 115.5(3) ? . . .
C34 C33 C32 112.3(3) ? . . .
C33 C34 C35 113.8(3) ? . . .
C32 C21 C22 112.9(2) ? . . .
C32 C21 C30 110.3(2) ? . . .
C32 C21 C29 111.0(3) ? . . .
C30 C21 C22 110.8(3) ? . . .
C21 C22 C28 118.3(3) ? . . .
C29 C21 C22 102.0(2) ? . . .
C21 C22 C23 121.7(3) ? . . .
C30 C21 C29 109.5(2) ? . . .
C21 C30 C31 126.7(3) ? . . .
C22 C23 C24 122.1(3) ? . . .
C28 C22 C23 119.6(3) ? . . .
C22 C28 C27 117.4(3) ? . . .
C23 C24 C25 116.6(3) ? . . .
C24 C25 C27 121.6(3) ? . . .
C25 C27 C28 122.6(3) ? . . .
O11 C6 H61 109.8599 ? . . .
O11 C6 H62 109.5636 ? . . .
O12 C6 H61 109.7821 ? . . .
O12 C6 H62 109.6614 ? . . .
O21 C26 H262 110.1708 ? . . .
O21 C26 H261 109.5628 ? . . .
O22 C26 H262 109.7166 ? . . .
O22 C26 H261 109.4102 ? . . .
O13 C9 H9 117.8862 ? . . .
O23 C29 H29 117.6611 ? . . .
C1 C9 H9 117.8979 ? . . .
C1 C12 H121 108.1142 ? . . .
C1 C12 H122 107.9359 ? . . .
C2 C3 H3 119.0052 ? . . .
C2 C8 H8 121.0408 ? . . .
C3 C4 H4 121.5285 ? . . .
H3 C3 C4 118.9011 ? . . .
H4 C4 C5 121.5920 ? . . .
H62 C6 H61 109.4659 ? . . .
C7 C8 H8 121.4159 ? . . .
C10 C11 H112 120.4144 ? . . .
C10 C11 H111 117.1165 ? . . .
H112 C11 H111 122.2959 ? . . .
H121 C12 C13 108.1498 ? . . .
C12 C13 H132 108.6762 ? . . .
H122 C12 C13 107.7225 ? . . .
C12 C13 H131 109.1045 ? . . .
H122 C12 H121 109.4639 ? . . .
H132 C13 C14 108.7959 ? . . .
H131 C13 C14 109.0811 ? . . .
C13 C14 H141 108.6462 ? . . .
C13 C14 H142 108.3603 ? . . .
H132 C13 H131 109.4576 ? . . .
H141 C14 C15 108.4226 ? . . .
H142 C14 C15 108.8591 ? . . .
C14 C15 H151 108.9639 ? . . .
C14 C15 H152 109.3243 ? . . .
C14 C15 H153 109.2947 ? . . .
H142 C14 H141 109.4627 ? . . .
H152 C15 H151 109.5939 ? . . .
H153 C15 H151 109.4706 ? . . .
H153 C15 H152 110.1727 ? . . .
C33 C32 H321 108.1618 ? . . .
H332 C33 C32 108.6300 ? . . .
C33 C32 H322 107.8930 ? . . .
H331 C33 C32 108.8739 ? . . .
H332 C33 C34 108.6639 ? . . .
H331 C33 C34 108.8724 ? . . .
C33 C34 H341 108.4622 ? . . .
C33 C34 H342 108.2498 ? . . .
H332 C33 H331 109.4665 ? . . .
H321 C32 C21 108.0250 ? . . .
H322 C32 C21 107.6565 ? . . .
H322 C32 H321 109.4559 ? . . .
H341 C34 C35 108.3676 ? . . .
H342 C34 C35 108.4590 ? . . .
C34 C35 H351 109.1455 ? . . .
C34 C35 H352 109.2024 ? . . .
C34 C35 H353 108.7537 ? . . .
H342 C34 H341 109.4596 ? . . .
H352 C35 H351 109.6046 ? . . .
H353 C35 H351 109.4671 ? . . .
H353 C35 H352 110.6415 ? . . .
C21 C29 H29 117.7492 ? . . .
C22 C23 H23 118.9871 ? . . .
C22 C28 H28 121.2112 ? . . .
C23 C24 H24 121.7343 ? . . .
H23 C23 C24 118.8726 ? . . .
H24 C24 C25 121.7058 ? . . .
H261 C26 H262 109.4601 ? . . .
C27 C28 H28 121.4217 ? . . .
C30 C31 H311 121.7978 ? . . .
C30 C31 H312 120.3383 ? . . .
H312 C31 H311 117.8296 ? . . .