# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009



data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Hansjoerg Streicher'
'Benoit Carbain'
'Patrick J. Collins'
'Stephen Martin'

_publ_contact_author_name        'Hansjoerg Streicher'
_publ_contact_author_email       H.STREICHER@SUSSEX.AC.UK

_publ_section_title              
;
Galactose-Conjugates of the Oseltamivir
Pharmacophore - New Tools for the Characterization of Influenza
Virus Neuraminidases
;
_publ_requested_category         FO

# Attachment 'iodine.cif'

data_dec707
_database_code_depnum_ccdc_archive 'CCDC 720847'

_audit_creation_date             2007-12-10T09:33:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C18 H31 I N2 O4'
_chemical_formula_sum            'C18 H31 I N2 O4'
_chemical_formula_weight         466.35
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.2334(15)
_cell_length_b                   4.9607(6)
_cell_length_c                   18.6244(19)
_cell_angle_alpha                90
_cell_angle_beta                 105.910(7)
_cell_angle_gamma                90
_cell_volume                     1086.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    30758
_cell_measurement_theta_min      3.395
_cell_measurement_theta_max      26.022
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.7795
_exptl_absorpt_correction_T_max  0.9809

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.840612E-1
_diffrn_orient_matrix_ub_12      0.165438E-1
_diffrn_orient_matrix_ub_13      -0.85115E-2
_diffrn_orient_matrix_ub_21      0.114724E-1
_diffrn_orient_matrix_ub_22      0.312792E-1
_diffrn_orient_matrix_ub_23      0.546111E-1
_diffrn_orient_matrix_ub_31      0.51994E-2
_diffrn_orient_matrix_ub_32      0.198454
_diffrn_orient_matrix_ub_33      -0.78979E-2
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_unetI/netI     0.1148
_diffrn_reflns_number            7090
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_full        25.95
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_reflns_number_total             3663
_reflns_number_gt                2313
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The H atoms on N were refined.

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^)+(0.0590P)^2^+3.0678P] 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     none
_refine_ls_number_reflns         3663
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.1772
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_diff_density_max         1.275
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.109

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
I I 0.27245(7) 0.5924(3) 0.45067(4) 0.0747(4) Uani 1 1 d . . .
O1 O 0.2482(7) 0.3805(15) 0.1689(4) 0.046(2) Uani 1 1 d . . .
O2 O 0.5185(11) 0.6756(17) 0.1530(6) 0.059(3) Uani 1 1 d . . .
O3 O 0.6576(8) -0.1655(16) 0.3359(6) 0.049(3) Uani 1 1 d . . .
O4 O 0.8009(7) 0.1432(15) 0.3443(4) 0.051(2) Uani 1 1 d . . .
N1 N 0.6280(10) 0.280(2) 0.3424(7) 0.044(3) Uani 1 1 d . . .
H1 H 0.668(12) 0.43(2) 0.341(7) 0.053 Uiso 1 1 d . . .
N2 N 0.4896(9) 0.259(2) 0.1934(5) 0.043(2) Uani 1 1 d . . .
H2 H 0.500(9) 0.07(3) 0.193(5) 0.051 Uiso 1 1 d . . .
C1 C 0.3354(10) 0.433(2) 0.3659(6) 0.042(3) Uani 1 1 d . . .
C2 C 0.4672(9) 0.413(2) 0.3877(6) 0.037(3) Uani 1 1 d . . .
H2A H 0.5003 0.5962 0.3917 0.045 Uiso 1 1 calc R . .
H2B H 0.4946 0.3242 0.437 0.045 Uiso 1 1 calc R . .
C3 C 0.5051(9) 0.254(2) 0.3301(6) 0.040(3) Uani 1 1 d . . .
H3 H 0.4866 0.0595 0.3348 0.048 Uiso 1 1 calc R . .
C4 C 0.4401(9) 0.353(2) 0.2512(6) 0.036(3) Uani 1 1 d . . .
H4 H 0.4428 0.5543 0.2515 0.043 Uiso 1 1 calc R . .
C5 C 0.3183(10) 0.270(2) 0.2369(6) 0.044(3) Uani 1 1 d . . .
H5 H 0.3136 0.0686 0.234 0.052 Uiso 1 1 calc R . .
C6 C 0.2731(9) 0.364(2) 0.3011(6) 0.040(3) Uani 1 1 d . . .
H6 H 0.1929 0.3734 0.2926 0.049 Uiso 1 1 calc R . .
C7 C 0.5312(13) 0.428(3) 0.1504(8) 0.049(4) Uani 1 1 d . . .
C8 C 0.5876(13) 0.298(2) 0.0972(8) 0.063(4) Uani 1 1 d . . .
H8A H 0.5455 0.3431 0.0459 0.094 Uiso 1 1 calc R . .
H8B H 0.5882 0.1018 0.1038 0.094 Uiso 1 1 calc R . .
H8C H 0.6658 0.3636 0.1073 0.094 Uiso 1 1 calc R . .
C9 C 0.1873(12) 0.183(2) 0.1161(6) 0.056(4) Uani 1 1 d . . .
H9 H 0.24 0.0303 0.1151 0.067 Uiso 1 1 calc R . .
C10 C 0.1591(15) 0.326(3) 0.0392(7) 0.082(5) Uani 1 1 d . . .
H10A H 0.1079 0.2081 0.0018 0.098 Uiso 1 1 calc R . .
H10B H 0.1174 0.4944 0.0423 0.098 Uiso 1 1 calc R . .
C11 C 0.2634(15) 0.394(4) 0.0118(10) 0.105(6) Uani 1 1 d . . .
H11A H 0.3138 0.515 0.0478 0.158 Uiso 1 1 calc R . .
H11B H 0.2386 0.4838 -0.0369 0.158 Uiso 1 1 calc R . .
H11C H 0.3042 0.2283 0.0071 0.158 Uiso 1 1 calc R . .
C12 C 0.0829(11) 0.070(4) 0.1374(7) 0.075(4) Uani 1 1 d . . .
H12A H 0.0475 -0.0727 0.1015 0.09 Uiso 1 1 calc R . .
H12B H 0.1084 -0.0128 0.1875 0.09 Uiso 1 1 calc R . .
C13 C -0.0052(12) 0.283(4) 0.1380(9) 0.082(5) Uani 1 1 d . . .
H13A H 0.0301 0.4298 0.1716 0.122 Uiso 1 1 calc R . .
H13B H -0.0667 0.2032 0.1553 0.122 Uiso 1 1 calc R . .
H13C H -0.0361 0.3544 0.0874 0.122 Uiso 1 1 calc R . .
C14 C 0.6926(8) 0.061(3) 0.3399(5) 0.042(3) Uani 1 1 d . . .
C15 C 0.8895(11) -0.063(2) 0.3408(8) 0.057(4) Uani 1 1 d . . .
C16 C 0.9101(11) -0.231(2) 0.4126(7) 0.054(3) Uani 1 1 d . . .
H16A H 0.8432 -0.3432 0.4103 0.081 Uiso 1 1 calc R . .
H16B H 0.9236 -0.1108 0.4559 0.081 Uiso 1 1 calc R . .
H16C H 0.9766 -0.3472 0.4175 0.081 Uiso 1 1 calc R . .
C17 C 0.9921(10) 0.115(3) 0.3454(8) 0.070(4) Uani 1 1 d . . .
H17A H 1.0578 0.0018 0.3454 0.105 Uiso 1 1 calc R . .
H17B H 1.0089 0.2211 0.3915 0.105 Uiso 1 1 calc R . .
H17C H 0.976 0.2366 0.3024 0.105 Uiso 1 1 calc R . .
C18 C 0.8508(12) -0.222(3) 0.2705(7) 0.058(3) Uani 1 1 d . . .
H18A H 0.7875 -0.3385 0.2733 0.088 Uiso 1 1 calc R . .
H18B H 0.9138 -0.3322 0.2641 0.088 Uiso 1 1 calc R . .
H18C H 0.8257 -0.0984 0.228 0.088 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
I 0.0442(4) 0.1245(9) 0.0562(5) -0.0239(7) 0.0151(3) 0.0004(8)
O1 0.048(5) 0.042(5) 0.044(4) 0.004(4) 0.005(4) 0.001(4)
O2 0.082(8) 0.037(7) 0.068(6) 0.002(4) 0.039(5) -0.009(5)
O3 0.043(6) 0.018(5) 0.086(7) -0.005(4) 0.015(5) 0.005(4)
O4 0.044(5) 0.027(5) 0.080(5) 0.005(4) 0.016(4) 0.018(4)
N1 0.039(6) 0.027(6) 0.066(7) 0.003(5) 0.012(5) -0.012(5)
N2 0.046(6) 0.030(5) 0.057(6) 0.006(5) 0.022(5) -0.001(5)
C1 0.039(7) 0.050(7) 0.036(6) -0.002(5) 0.009(5) 0.013(6)
C2 0.034(6) 0.035(6) 0.040(6) 0.001(5) 0.004(5) 0.001(5)
C3 0.025(6) 0.031(6) 0.064(7) -0.002(5) 0.012(5) -0.008(5)
C4 0.037(7) 0.031(6) 0.043(6) -0.001(5) 0.016(5) -0.018(5)
C5 0.042(7) 0.043(6) 0.043(6) -0.002(5) 0.007(5) 0.001(6)
C6 0.026(6) 0.050(7) 0.050(7) 0.001(5) 0.018(5) -0.010(5)
C7 0.041(8) 0.041(9) 0.065(9) -0.004(7) 0.015(7) 0.010(7)
C8 0.075(10) 0.038(7) 0.089(10) 0.009(7) 0.046(8) 0.012(7)
C9 0.062(8) 0.058(9) 0.038(6) -0.016(5) -0.004(6) 0.001(6)
C10 0.103(13) 0.073(11) 0.048(8) -0.007(7) -0.014(8) 0.000(9)
C11 0.077(12) 0.172(18) 0.074(11) 0.022(11) 0.032(10) 0.012(12)
C12 0.079(9) 0.068(9) 0.066(7) 0.011(10) -0.001(6) -0.011(12)
C13 0.046(9) 0.108(12) 0.091(11) 0.027(10) 0.018(8) 0.001(9)
C14 0.034(6) 0.039(8) 0.048(5) -0.007(7) 0.004(4) 0.017(8)
C15 0.044(8) 0.033(6) 0.096(10) -0.003(7) 0.022(7) 0.022(6)
C16 0.061(9) 0.037(7) 0.063(8) 0.000(6) 0.016(7) 0.017(7)
C17 0.045(7) 0.033(7) 0.135(11) 0.003(10) 0.028(7) 0.001(9)
C18 0.058(9) 0.049(8) 0.072(9) -0.002(7) 0.024(7) 0.003(7)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
I C1 2.093(11) . ?
O1 C5 1.430(12) . ?
O1 C9 1.441(13) . ?
O2 C7 1.242(14) . ?
O3 C14 1.196(16) . ?
O4 C14 1.368(14) . ?
O4 C15 1.504(14) . ?
N1 C14 1.355(16) . ?
N1 C3 1.464(15) . ?
N1 H1 0.91(12) . ?
N2 C7 1.351(17) . ?
N2 C4 1.449(14) . ?
N2 H2 0.96(16) . ?
C1 C6 1.284(14) . ?
C1 C2 1.553(15) . ?
C2 C3 1.504(15) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.546(15) . ?
C3 H3 1 . ?
C4 C5 1.499(15) . ?
C4 H4 1 . ?
C5 C6 1.522(15) . ?
C5 H5 1 . ?
C6 H6 0.95 . ?
C7 C8 1.498(19) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C12 1.543(19) . ?
C9 C10 1.548(17) . ?
C9 H9 1 . ?
C10 C11 1.54(2) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 C13 1.51(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C15 C18 1.489(18) . ?
C15 C17 1.517(19) . ?
C15 C16 1.539(18) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?

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 O1 C9 114.6(8) . . ?
C14 O4 C15 119.5(10) . . ?
C14 N1 C3 120.4(10) . . ?
C14 N1 H1 111(9) . . ?
C3 N1 H1 127(9) . . ?
C7 N2 C4 122.9(10) . . ?
C7 N2 H2 123(6) . . ?
C4 N2 H2 114(6) . . ?
C6 C1 C2 122.4(10) . . ?
C6 C1 I 124.2(9) . . ?
C2 C1 I 113.4(7) . . ?
C3 C2 C1 110.4(8) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 C2 110.2(9) . . ?
N1 C3 C4 111.0(9) . . ?
C2 C3 C4 109.4(9) . . ?
N1 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
N2 C4 C5 112.2(9) . . ?
N2 C4 C3 113.2(9) . . ?
C5 C4 C3 108.0(8) . . ?
N2 C4 H4 107.8 . . ?
C5 C4 H4 107.8 . . ?
C3 C4 H4 107.8 . . ?
O1 C5 C4 112.1(9) . . ?
O1 C5 C6 108.6(9) . . ?
C4 C5 C6 109.5(8) . . ?
O1 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C1 C6 C5 124.7(10) . . ?
C1 C6 H6 117.6 . . ?
C5 C6 H6 117.6 . . ?
O2 C7 N2 121.3(15) . . ?
O2 C7 C8 122.4(16) . . ?
N2 C7 C8 116.2(11) . . ?
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 . . ?
O1 C9 C12 112.3(11) . . ?
O1 C9 C10 105.4(10) . . ?
C12 C9 C10 114.4(11) . . ?
O1 C9 H9 108.2 . . ?
C12 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C11 C10 C9 114.4(13) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
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 . . ?
C13 C12 C9 113.0(14) . . ?
C13 C12 H12A 109 . . ?
C9 C12 H12A 109 . . ?
C13 C12 H12B 109 . . ?
C9 C12 H12B 109 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 N1 123.8(11) . . ?
O3 C14 O4 127.5(11) . . ?
N1 C14 O4 108.7(12) . . ?
C18 C15 O4 109.8(10) . . ?
C18 C15 C17 114.6(12) . . ?
O4 C15 C17 101.5(10) . . ?
C18 C15 C16 114.4(11) . . ?
O4 C15 C16 106.2(10) . . ?
C17 C15 C16 109.3(11) . . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

#===END