Electronic Supplementary Material for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2005

data_global

_audit_creation_method           maXus

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Joern B. Christensen'
'Ulrik Boas'
'Knud J. Jensen'
'Mikkel Jessing'
'Michael Pittelkow'

_publ_contact_author_name        'Jorn B. Christensen'
_publ_contact_author_address     
;
Associate Professor Jorn B. Christensen
The H. C. Orsted Institute
Department of Chemistry
University of Copenhagen
Universitetsparken 5
DK-2100
Denmark.
;
_publ_contact_author_email       jbc@kiku.dk
_publ_contact_author_fax         '++ 45 35320112 '
_publ_contact_author_phone       '++ 45 35320194'

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Role of the peri-effect in synthesis and reactivity
of highly substituted naphthaldehydes: a novel backbone amide linker for
solid-phase synthesis
;
_publ_section_abstract           
;
?
;
_publ_section_comment            
;
The study of the titled structure was undertaken to establish its three
dimensional structure.  Geometries are tabulated below.  All diagrams and
calculations were performed using maXus (Bruker Nonius, Delft & MacScience,
Japan).
;

_publ_section_acknowledgements   
;
The authers acknowledge Peter Hammersh?j and Magnus Magnussen for their
help with the crystal structures.
;

_publ_section_references         
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(1999). maXus  Computer Program for the Solution and Refinement of
Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan
& The University of Glasgow.

Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot
Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge,
Tennessee, USA.

Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276,
edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326,
New York:Academic Press.

Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L.,
Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R.
(1999). J. Appl. Cryst. 32, 115-119.

Sheldrick, G. M. (1997).  SHELXL97.  Program for the Refinement of Crystal
Structures.  University of Gottingen, Germany.

;

data_compound_1
_database_code_depnum_ccdc_archive 'CCDC 248480'

_chemical_compound_source        'Local laboratory'
_exptl_crystal_description       Needles
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_F_000             520
_cell_measurement_temperature    122
_refine_ls_hydrogen_treatment    constr

_diffrn_measurement_device       KappaCCD
_computing_data_collection       KappaCCD
_computing_data_reduction        'EvalCCD(Duisberg, 2003)'

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36

loop_
_diffrn_radiation_wavelength
0.71073
_diffrn_radiation_wavelength_id  all

_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_special_details           
;
?
;
_chemical_formula_weight         246.262
_diffrn_radiation_type           ' MoK\a'

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
'-X,+Y+ 1/2,-Z+ 1/2'
'+X,-Y+ 1/2,+Z+ 1/2'

_symmetry_space_group_name_H-M   'P 21/c        '
_symmetry_cell_setting           Monoclinic
_chemical_formula_moiety         'C14 H14 O4 '
_chemical_formula_sum            'C14 H14 O4 '
_chemical_name_systematic        
;
?
;
_cell_length_a                   3.9763(3)
_cell_length_b                   11.8245(10)
_cell_length_c                   24.323(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.353(7)
_cell_angle_gamma                90.00
_cell_volume                     1139.2(2)
_diffrn_reflns_number            30841
_diffrn_reflns_theta_max         31.98
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_full        31.98
_cell_measurement_reflns_used    10359
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      31.98
_diffrn_measurement_method       CCD
_computing_cell_refinement       'COLLECT (Nonius, 1999)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

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'

_exptl_absorpt_coefficient_mu    0.105
_reflns_number_total             3800
_reflns_number_gt                2620
_reflns_threshold_expression     >2sigma(I)

_computing_structure_refinement  'SHELXL-97 (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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3800
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1900
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_restrained_S_all      1.255
_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
O1 O 0.9889(3) 0.27485(9) 0.82596(4) 0.0197(3) Uani 1 1 d . . .
O2 O 0.3792(3) 0.01267(9) 0.56449(4) 0.0180(3) Uani 1 1 d . . .
O3 O 0.1800(3) 0.40078(9) 0.60043(4) 0.0171(3) Uani 1 1 d . . .
C4 C 0.6417(4) 0.18727(12) 0.68648(6) 0.0128(3) Uani 1 1 d . . .
O5 O -0.0558(3) 0.28229(10) 0.50325(5) 0.0249(3) Uani 1 1 d . . .
C6 C 0.6070(4) 0.09187(12) 0.65128(6) 0.0139(3) Uani 1 1 d . . .
C7 C 0.8397(4) 0.27290(13) 0.77344(6) 0.0153(3) Uani 1 1 d . . .
C8 C 0.4266(4) 0.09992(13) 0.60089(6) 0.0139(3) Uani 1 1 d . . .
C9 C 0.3205(4) 0.29867(13) 0.61535(6) 0.0143(3) Uani 1 1 d . . .
C10 C 0.5371(4) 0.38651(13) 0.70386(6) 0.0159(3) Uani 1 1 d . . .
C11 C 0.8132(4) 0.17932(13) 0.73999(6) 0.0145(3) Uani 1 1 d . . .
C12 C 0.4988(4) 0.29186(12) 0.66834(6) 0.0134(3) Uani 1 1 d . . .
C13 C 0.2744(4) 0.20403(12) 0.58177(6) 0.0137(3) Uani 1 1 d . . .
C14 C 1.1320(4) 0.17273(13) 0.84818(6) 0.0210(4) Uani 1 1 d . . .
C15 C 0.3581(4) 0.46303(13) 0.56119(6) 0.0206(3) Uani 1 1 d . . .
C16 C 0.0515(4) 0.20211(13) 0.53007(6) 0.0178(3) Uani 1 1 d . . .
C17 C 0.7022(4) 0.37733(13) 0.75498(6) 0.0172(3) Uani 1 1 d . . .
C18 C 0.5300(4) -0.09312(12) 0.58076(6) 0.0185(3) Uani 1 1 d . . .
H6 H 0.7354 0.0217 0.6623 0.017 Uiso 1 1 d R . .
H10 H 0.4235 0.4533 0.6923 0.019 Uiso 1 1 d R . .
H11 H 0.9057 0.1068 0.7528 0.017 Uiso 1 1 d R . .
H14A H 1.2847 0.1466 0.8306 0.025 Uiso 1 1 d R . .
H14B H 1.1935 0.1862 0.8860 0.025 Uiso 1 1 d R . .
H14C H 0.9728 0.1111 0.8473 0.025 Uiso 1 1 d R . .
H15A H 0.2211 0.5254 0.5517 0.025 Uiso 1 1 d R . .
H15B H 0.5572 0.4800 0.5752 0.025 Uiso 1 1 d R . .
H15C H 0.3765 0.4265 0.5362 0.025 Uiso 1 1 d R . .
H16 H -0.0013 0.1386 0.5198 0.021 Uiso 1 1 d R . .
H17 H 0.7410 0.4390 0.7784 0.021 Uiso 1 1 d R . .
H18A H 0.4616 -0.1169 0.6106 0.022 Uiso 1 1 d R . .
H18B H 0.4601 -0.1432 0.5517 0.022 Uiso 1 1 d R . .
H18C H 0.7873 -0.0848 0.5879 0.022 Uiso 1 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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0263(6) 0.0175(6) 0.0140(5) -0.0019(4) -0.0054(4) 0.0015(5)
O2 0.0230(6) 0.0149(5) 0.0149(5) -0.0022(4) -0.0042(4) 0.0036(4)
O3 0.0193(6) 0.0144(5) 0.0180(5) 0.0048(4) 0.0038(4) 0.0040(4)
C4 0.0117(6) 0.0135(7) 0.0133(7) 0.0017(5) 0.0010(5) 0.0004(5)
O5 0.0292(7) 0.0227(7) 0.0211(6) 0.0044(5) -0.0080(5) 0.0029(5)
C6 0.0142(7) 0.0136(7) 0.0137(6) 0.0014(5) 0.0009(5) 0.0010(6)
C7 0.0150(7) 0.0185(8) 0.0123(7) 0.0003(5) 0.0004(5) -0.0020(6)
C8 0.0143(7) 0.0151(7) 0.0125(6) 0.0002(5) 0.0022(5) -0.0007(5)
C9 0.0126(7) 0.0156(7) 0.0150(7) 0.0032(5) 0.0029(5) 0.0020(5)
C10 0.0168(7) 0.0135(7) 0.0179(7) 0.0010(5) 0.0035(6) 0.0011(6)
C11 0.0155(7) 0.0144(7) 0.0133(7) 0.0012(5) 0.0001(5) 0.0002(6)
C12 0.0133(7) 0.0136(7) 0.0137(7) 0.0029(5) 0.0037(5) 0.0007(5)
C13 0.0135(7) 0.0147(7) 0.0128(6) 0.0033(5) 0.0005(5) 0.0008(5)
C14 0.0259(8) 0.0182(8) 0.0177(7) 0.0027(6) -0.0043(6) -0.0012(6)
C15 0.0206(8) 0.0184(8) 0.0232(8) 0.0052(6) 0.0030(6) 0.0007(6)
C16 0.0167(7) 0.0201(8) 0.0163(7) -0.0010(6) -0.0005(6) 0.0007(6)
C17 0.0198(8) 0.0152(7) 0.0167(7) -0.0023(5) 0.0021(6) -0.0007(6)
C18 0.0216(8) 0.0153(7) 0.0179(7) -0.0024(6) -0.0021(6) 0.0029(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
O1 C7 1.3607(17) . ?
O1 C14 1.4212(18) . ?
O2 C8 1.3617(17) . ?
O2 C18 1.4281(17) . ?
O3 C9 1.3661(17) . ?
O3 C15 1.4398(18) . ?
C4 C12 1.4153(19) . ?
C4 C6 1.416(2) . ?
C4 C11 1.4184(19) . ?
O5 C16 1.2073(18) . ?
C6 C8 1.3680(19) . ?
C7 C11 1.372(2) . ?
C7 C17 1.408(2) . ?
C8 C13 1.431(2) . ?
C9 C13 1.388(2) . ?
C9 C12 1.418(2) . ?
C10 C17 1.358(2) . ?
C10 C12 1.414(2) . ?
C13 C16 1.4739(19) . ?
C6 H6 0.9990 . ?
C10 H10 0.9406 . ?
C11 H11 0.9734 . ?
C14 H14A 0.8323 . ?
C14 H14B 0.9449 . ?
C14 H14C 0.9641 . ?
C15 H15A 0.9337 . ?
C15 H15B 0.8573 . ?
C15 H15C 0.7552 . ?
C16 H16 0.8129 . ?
C17 H17 0.9308 . ?
C18 H18A 0.8445 . ?
C18 H18B 0.9453 . ?
C18 H18C 1.0271 . ?

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
C7 O1 C14 118.02(12) . . ?
C8 O2 C18 116.91(11) . . ?
C9 O3 C15 114.49(11) . . ?
C12 C4 C6 119.51(13) . . ?
C12 C4 C11 119.44(13) . . ?
C6 C4 C11 121.05(13) . . ?
C8 C6 C4 120.15(13) . . ?
O1 C7 C11 125.09(13) . . ?
O1 C7 C17 114.19(13) . . ?
C11 C7 C17 120.71(13) . . ?
O2 C8 C6 124.17(13) . . ?
O2 C8 C13 114.21(12) . . ?
C6 C8 C13 121.62(13) . . ?
O3 C9 C13 121.77(13) . . ?
O3 C9 C12 116.87(13) . . ?
C13 C9 C12 121.25(13) . . ?
C17 C10 C12 120.89(14) . . ?
C7 C11 C4 119.76(13) . . ?
C4 C12 C10 118.85(13) . . ?
C4 C12 C9 119.21(13) . . ?
C10 C12 C9 121.94(13) . . ?
C9 C13 C8 118.18(13) . . ?
C9 C13 C16 123.56(13) . . ?
C8 C13 C16 117.99(13) . . ?
O5 C16 C13 127.33(15) . . ?
C10 C17 C7 120.33(14) . . ?
C8 C6 H6 121.0 . . ?
C4 C6 H6 118.6 . . ?
C17 C10 H10 121.5 . . ?
C12 C10 H10 117.3 . . ?
C7 C11 H11 120.8 . . ?
C4 C11 H11 119.4 . . ?
O1 C14 H14A 113.9 . . ?
O1 C14 H14B 106.7 . . ?
H14A C14 H14B 115.2 . . ?
O1 C14 H14C 113.2 . . ?
H14A C14 H14C 102.4 . . ?
H14B C14 H14C 105.1 . . ?
O3 C15 H15A 104.9 . . ?
O3 C15 H15B 110.3 . . ?
H15A C15 H15B 114.3 . . ?
O3 C15 H15C 109.2 . . ?
H15A C15 H15C 110.3 . . ?
H15B C15 H15C 107.6 . . ?
O5 C16 H16 119.3 . . ?
C13 C16 H16 113.3 . . ?
C10 C17 H17 122.6 . . ?
C7 C17 H17 116.9 . . ?
O2 C18 H18A 111.7 . . ?
O2 C18 H18B 104.6 . . ?
H18A C18 H18B 109.8 . . ?
O2 C18 H18C 110.5 . . ?
H18A C18 H18C 106.1 . . ?
H18B C18 H18C 114.2 . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.077

data_compound_2
_database_code_depnum_ccdc_archive 'CCDC 248481'

_chemical_compound_source        'Local laboratory'
_exptl_crystal_description       Needles
_exptl_crystal_colour            Yellow
_cell_measurement_temperature    122
_refine_ls_hydrogen_treatment    constr
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06

# Submission details

_diffrn_measurement_device       KappaCCD
_computing_data_collection       KappaCCD
_computing_data_reduction        'EvalCCD (Duisenberg, 2003)'

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

loop_
_diffrn_radiation_wavelength
0.71073
_diffrn_radiation_wavelength_id  all

_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_special_details           
;
?
;
_chemical_formula_weight         232.235
_diffrn_radiation_type           ' MoK\a'

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
'-X,+Y+ 1/2,-Z+ 1/2'
'+X,-Y+ 1/2,+Z+ 1/2'

_symmetry_space_group_name_H-M   'P 21/c        '
_symmetry_cell_setting           Monoclinic
_chemical_formula_moiety         'C13 H12 O4 '
_chemical_formula_sum            'C13 H12 O4 '
_chemical_name_systematic        
;
?
;
_cell_length_a                   18.985(3)
_cell_length_b                   3.9181(6)
_cell_length_c                   14.504(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.443(11)
_cell_angle_gamma                90.00
_cell_volume                     1049.3(3)
_diffrn_reflns_number            38108
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.10
_diffrn_reflns_theta_full        30.00
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.10
_cell_measurement_theta_max      30.00
_diffrn_measurement_method       CCD
_computing_cell_refinement       'COLLECT (Nonius. 1999)'
_computing_structure_solution    'SIR97 (ALTOMARE, 1999)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

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'

_exptl_absorpt_coefficient_mu    0.109
_reflns_number_total             3077
_reflns_number_gt                2159
_reflns_threshold_expression     >2sigma(I)

_computing_structure_refinement  'SHELXL-97 (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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3077
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_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
O1 O 0.23490(5) -0.2771(3) 0.49990(7) 0.0210(3) Uani 1 1 d . . .
O2 O 0.06153(5) 0.1543(3) 0.09177(7) 0.0192(3) Uani 1 1 d . . .
O3 O 0.36472(6) -0.2504(3) 0.60069(8) 0.0282(3) Uani 1 1 d . . .
O4 O 0.42443(5) 0.2755(3) 0.39717(7) 0.0215(3) Uani 1 1 d . . .
C5 C 0.11303(7) 0.1012(4) 0.17281(10) 0.0151(3) Uani 1 1 d . . .
C6 C 0.23311(7) 0.1353(4) 0.27448(10) 0.0144(3) Uani 1 1 d . . .
C7 C 0.13518(8) -0.1443(4) 0.32870(10) 0.0165(3) Uani 1 1 d . . .
C8 C 0.18405(7) 0.2036(4) 0.18701(10) 0.0154(3) Uani 1 1 d . . .
C9 C 0.35347(7) 0.1785(4) 0.37446(10) 0.0171(3) Uani 1 1 d . . .
C10 C 0.08821(7) -0.0742(4) 0.24398(10) 0.0169(3) Uani 1 1 d . . .
C11 C 0.33093(7) -0.0029(4) 0.44832(10) 0.0169(3) Uani 1 1 d . . .
C12 C 0.30659(8) 0.2439(4) 0.28986(10) 0.0165(3) Uani 1 1 d . . .
C13 C 0.08405(8) 0.3187(4) 0.01540(10) 0.0195(3) Uani 1 1 d . . .
C14 C 0.25863(7) -0.1081(4) 0.43266(10) 0.0158(3) Uani 1 1 d . . .
C15 C 0.38125(8) -0.0909(5) 0.53500(11) 0.0232(4) Uani 1 1 d . . .
C16 C 0.45085(8) 0.4420(4) 0.32463(11) 0.0239(4) Uani 1 1 d . . .
C17 C 0.20834(7) -0.0394(4) 0.34611(10) 0.0148(3) Uani 1 1 d . . .
H1 H 0.2730 -0.3107 0.5502 0.025 Uiso 1 1 d R . .
H7 H 0.1193 -0.2754 0.3776 0.020 Uiso 1 1 d R . .
H8 H 0.2028 0.3172 0.1386 0.019 Uiso 1 1 d R . .
H10 H 0.0385 -0.1403 0.2318 0.020 Uiso 1 1 d R . .
H12 H 0.3224 0.3719 0.2424 0.020 Uiso 1 1 d R . .
H13A H 0.1189 0.2072 0.0023 0.023 Uiso 1 1 d R . .
H13B H 0.1019 0.5445 0.0300 0.023 Uiso 1 1 d R . .
H13C H 0.0440 0.3203 -0.0382 0.023 Uiso 1 1 d R . .
H15 H 0.4314 -0.0033 0.5425 0.028 Uiso 1 1 d R . .
H16A H 0.4445 0.3003 0.2696 0.029 Uiso 1 1 d R . .
H16B H 0.4330 0.6366 0.3085 0.029 Uiso 1 1 d R . .
H16C H 0.5018 0.4781 0.3501 0.029 Uiso 1 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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0190(5) 0.0286(6) 0.0155(5) 0.0046(5) 0.0043(4) -0.0001(5)
O2 0.0148(5) 0.0257(6) 0.0154(5) 0.0014(4) 0.0001(4) -0.0016(4)
O3 0.0246(6) 0.0400(7) 0.0181(6) 0.0066(5) 0.0011(4) -0.0015(5)
O4 0.0126(5) 0.0282(6) 0.0223(6) 0.0033(5) 0.0010(4) -0.0037(4)
C5 0.0145(6) 0.0147(7) 0.0152(6) -0.0024(6) 0.0018(5) 0.0018(5)
C6 0.0131(6) 0.0149(7) 0.0148(7) -0.0020(6) 0.0024(5) 0.0009(5)
C7 0.0168(7) 0.0166(7) 0.0174(7) -0.0007(6) 0.0066(5) -0.0007(5)
C8 0.0145(6) 0.0173(7) 0.0147(6) -0.0005(6) 0.0037(5) -0.0003(5)
C9 0.0127(6) 0.0191(7) 0.0190(7) -0.0026(6) 0.0027(5) -0.0001(5)
C10 0.0129(6) 0.0185(7) 0.0193(7) -0.0027(6) 0.0036(5) -0.0011(6)
C11 0.0151(6) 0.0190(7) 0.0155(7) -0.0019(6) 0.0015(5) 0.0007(6)
C12 0.0153(7) 0.0182(7) 0.0162(7) 0.0004(6) 0.0042(5) -0.0015(5)
C13 0.0185(7) 0.0238(8) 0.0156(7) 0.0004(6) 0.0027(5) -0.0006(6)
C14 0.0158(7) 0.0168(7) 0.0157(7) -0.0001(6) 0.0054(5) 0.0005(5)
C15 0.0191(7) 0.0293(9) 0.0193(7) 0.0002(7) 0.0009(6) -0.0005(6)
C16 0.0152(7) 0.0268(9) 0.0293(8) 0.0067(7) 0.0043(6) -0.0013(6)
C17 0.0146(6) 0.0145(7) 0.0152(6) -0.0021(5) 0.0035(5) 0.0010(5)

_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
O1 C14 1.3405(17) . ?
O2 C5 1.3588(16) . ?
O2 C13 1.4299(17) . ?
O3 C15 1.2394(19) . ?
O4 C9 1.3645(16) . ?
O4 C16 1.4244(18) . ?
C5 C8 1.3758(19) . ?
C5 C10 1.409(2) . ?
C6 C17 1.413(2) . ?
C6 C8 1.4139(19) . ?
C6 C12 1.4255(19) . ?
C7 C10 1.368(2) . ?
C7 C17 1.4137(19) . ?
C9 C12 1.362(2) . ?
C9 C11 1.431(2) . ?
C11 C14 1.4003(19) . ?
C11 C15 1.4329(19) . ?
C14 C17 1.4151(19) . ?
O1 H1 0.9093 . ?
C7 H7 0.9775 . ?
C8 H8 0.9659 . ?
C10 H10 0.9538 . ?
C12 H12 0.9551 . ?
C13 H13A 0.8508 . ?
C13 H13B 0.9538 . ?
C13 H13C 0.9525 . ?
C15 H15 0.9943 . ?
C16 H16A 0.9572 . ?
C16 H16B 0.8455 . ?
C16 H16C 0.9617 . ?

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 O2 C13 117.04(11) . . ?
C9 O4 C16 116.53(11) . . ?
O2 C5 C8 124.60(13) . . ?
O2 C5 C10 114.36(12) . . ?
C8 C5 C10 121.04(13) . . ?
C17 C6 C8 119.28(12) . . ?
C17 C6 C12 120.70(12) . . ?
C8 C6 C12 120.02(13) . . ?
C10 C7 C17 120.68(13) . . ?
C5 C8 C6 119.82(13) . . ?
C12 C9 O4 124.52(14) . . ?
C12 C9 C11 121.41(13) . . ?
O4 C9 C11 114.07(12) . . ?
C7 C10 C5 119.79(13) . . ?
C14 C11 C9 118.49(12) . . ?
C14 C11 C15 120.01(13) . . ?
C9 C11 C15 121.44(13) . . ?
C9 C12 C6 119.70(14) . . ?
O1 C14 C11 120.66(12) . . ?
O1 C14 C17 117.90(12) . . ?
C11 C14 C17 121.45(13) . . ?
O3 C15 C11 124.01(14) . . ?
C6 C17 C7 119.39(12) . . ?
C6 C17 C14 118.24(12) . . ?
C7 C17 C14 122.36(13) . . ?
C14 O1 H1 108.4 . . ?
C10 C7 H7 120.7 . . ?
C17 C7 H7 118.6 . . ?
C5 C8 H8 122.6 . . ?
C6 C8 H8 117.6 . . ?
C7 C10 H10 121.5 . . ?
C5 C10 H10 118.8 . . ?
C9 C12 H12 120.0 . . ?
C6 C12 H12 120.2 . . ?
O2 C13 H13A 109.3 . . ?
O2 C13 H13B 113.7 . . ?
H13A C13 H13B 105.7 . . ?
O2 C13 H13C 108.1 . . ?
H13A C13 H13C 109.6 . . ?
H13B C13 H13C 110.5 . . ?
O3 C15 H15 119.9 . . ?
C11 C15 H15 116.0 . . ?
O4 C16 H16A 110.7 . . ?
O4 C16 H16B 115.5 . . ?
H16A C16 H16B 109.1 . . ?
O4 C16 H16C 106.2 . . ?
H16A C16 H16C 109.0 . . ?
H16B C16 H16C 106.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.066