Electronic Supplementary Material for CrystEngComm
This Journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
#==============================================================================

# 0. AUDIT DETAILS

_audit_creation_date             'Dec 12 13:33:54 2004'
_audit_creation_method           'PLATON <TABLE ACC> option'
_audit_update_record             
;
?
;

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

# 1. SUBMISSION DETAILS

_publ_contact_author_name        'Goverdhan Mehta'
_publ_contact_author_address     
;
Department of Organic Chemistry
Indian Institute of Science
Bangalore
560 012
INDIA
;

_publ_section_title              
;
Additive induced polymorphous behaviour of a
conformationally locked hexol
;
_publ_contact_author_email       gm@orgchem.iisc.ernet.in
_publ_contact_author_fax         +91-80-23600936
_publ_contact_author_phone       +91-80-22932850

# Insert blank lines between references

_publ_section_references         
;
Allen, F.H. & Kennard, O. (1993).
Chem. Des. Autom. News., 8, 31-37.

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

Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P.,
Garcia-Granda, S., Gould, R.O., Smits, J.M.M. &
Smykalla, C. (1999) The DIRDIF99 program system,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.

Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410.

Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320.

Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.

Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft,
The Netherlands.

Flack, H.D. (1983). Acta Cryst. A39, 876-881.

LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.

Mackay, A.L. (1984). Acta Cryst. A40, 165-166.

Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.

Nonius (1998). Collect Software, Nonius, Delft, The Netherlands.

North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968).
Acta Cryst. A24, 351-359.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326.

Sheldrick, G.M. SHELXL93. Program for crystal structure
refinement. University of Gottingen, Germany, 1993.

Sheldrick, G.M. SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany, 1997.

Sheldrick, G.M. SHELXS86. Program for Crystal Structure
solution. University of Gottingen, Germany, 1986.

Sheldrick, G.M. SHELXS97. Program for Crystal Structure
solution. University of Gottingen, Germany, 1997.

Spek, A.L. (1987). Acta Cryst. C43, 1233-1235.

Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579.

Spek, A.L. (1990). Acta Cryst. A46, C-34.

Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht
University, The Netherlands.

Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_acknowledgements   
; ?
;
_publ_section_figure_captions    
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;
loop_
_publ_author_name
G.Mehta
S.Sen

#===END

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

data_hexol_monohydrate
_database_code_depnum_ccdc_archive 'CCDC 620926'

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
all trans-perhydro-2,3,4a,6,7,8a-naphthalenehexaol monohydrate
;
_chemical_name_common            
'all trans-perhydro-2,3,4a,6,7,8a-naphthalenehexaol monohydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H18 O6, H2 O'
_chemical_formula_structural     ?
_chemical_formula_sum            'C10 H20 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         252.26
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   '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                   6.663(2)
_cell_length_b                   9.045(3)
_cell_length_c                   10.707(3)
_cell_angle_alpha                72.385(5)
_cell_angle_beta                 81.655(5)
_cell_angle_gamma                69.238(5)
_cell_volume                     574.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.124
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min  0.9327
_exptl_absorpt_correction_T_max  0.9709

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoKa
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_reflns_number            4399
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.85
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.991

_diffrn_reflns_reduction_process 
;
;

_reflns_number_total             2187
_reflns_number_gt                1923
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

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

# 8. REFINEMENT DATA

_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^)+(0.0602P)^2^+0.1265P] 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_extinction_coef       ?
_refine_ls_number_reflns         2187
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT 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
O1W O 0.8023(3) 0.95245(18) 0.23935(15) 0.0613(4) Uani 1 1 d . . .
O1 O 0.72007(19) 0.21777(13) 0.33775(10) 0.0430(3) Uani 1 1 d . . .
O2 O 0.76257(18) 0.14953(12) 0.68940(10) 0.0390(3) Uani 1 1 d . . .
O3 O 0.50178(16) 0.46187(11) 0.67925(9) 0.0318(2) Uani 1 1 d . . .
O4 O 0.66697(18) 0.79303(13) 1.11186(10) 0.0405(3) Uani 1 1 d . . .
O5 O 0.77539(19) 0.83319(12) 0.76323(10) 0.0423(3) Uani 1 1 d . . .
O6 O 1.06276(17) 0.52394(11) 0.82300(9) 0.0332(3) Uani 1 1 d . . .
C1 C 0.6414(2) 0.19758(16) 0.47180(14) 0.0335(3) Uani 1 1 d . . .
C2 C 0.8062(2) 0.20877(16) 0.55128(13) 0.0324(3) Uani 1 1 d . . .
C3 C 0.8041(2) 0.38408(16) 0.52638(13) 0.0299(3) Uani 1 1 d . . .
C4 C 0.5799(2) 0.50377(15) 0.54434(12) 0.0258(3) Uani 1 1 d . . .
C5 C 0.5816(2) 0.67998(16) 0.51436(14) 0.0314(3) Uani 1 1 d . . .
C6 C 0.7970(2) 0.81332(16) 0.99268(13) 0.0329(3) Uani 1 1 d . . .
C7 C 0.6918(2) 0.77634(16) 0.89340(14) 0.0338(3) Uani 1 1 d . . .
C8 C 0.7173(2) 0.59418(16) 0.92828(14) 0.0315(3) Uani 1 1 d . . .
C9 C 0.9496(2) 0.48187(15) 0.94761(12) 0.0260(3) Uani 1 1 d . . .
C10 C 1.0295(2) 0.69998(15) 1.01467(13) 0.0299(3) Uani 1 1 d . . .
H2W H 0.757(3) 1.034(3) 0.265(2) 0.069(7) Uiso 1 1 d . . .
H1W H 0.932(4) 0.920(3) 0.248(2) 0.070(7) Uiso 1 1 d . . .
H1O H 0.6778 0.3154 0.2978 0.064 Uiso 1 1 calc R . .
H2O H 0.7665 0.0538 0.7066 0.059 Uiso 1 1 calc R . .
H3O H 0.5559 0.3629 0.7122 0.048 Uiso 1 1 calc R . .
H5O H 0.8891 0.7641 0.7498 0.063 Uiso 1 1 calc R . .
H4O H 0.6850 0.8455 1.1572 0.061 Uiso 1 1 calc R . .
H6O H 1.1683 0.4448 0.8161 0.050 Uiso 1 1 calc R . .
H1 H 0.6312 0.0868 0.5055 0.040 Uiso 1 1 calc R . .
H2 H 0.9498 0.1411 0.5279 0.039 Uiso 1 1 calc R . .
H3A H 0.8591 0.4206 0.4376 0.036 Uiso 1 1 calc R . .
H3B H 0.8993 0.3858 0.5861 0.036 Uiso 1 1 calc R . .
H5A H 0.6759 0.6836 0.5736 0.038 Uiso 1 1 calc R . .
H5B H 0.6392 0.7122 0.4256 0.038 Uiso 1 1 calc R . .
H6 H 0.7942 0.9277 0.9613 0.039 Uiso 1 1 calc R . .
H7 H 0.5378 0.8379 0.8964 0.041 Uiso 1 1 calc R . .
H8A H 0.6329 0.5669 1.0082 0.038 Uiso 1 1 calc R . .
H8B H 0.6605 0.5740 0.8589 0.038 Uiso 1 1 calc R . .
H10A H 1.1159 0.7245 0.9351 0.036 Uiso 1 1 calc R . .
H10B H 1.0853 0.7216 1.0837 0.036 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
O1W 0.0565(9) 0.0522(8) 0.0825(11) -0.0393(7) -0.0220(7) -0.0016(7)
O1 0.0583(7) 0.0319(5) 0.0361(6) -0.0159(4) 0.0044(5) -0.0086(5)
O2 0.0483(6) 0.0262(5) 0.0338(6) -0.0018(4) -0.0014(5) -0.0072(5)
O3 0.0386(6) 0.0269(5) 0.0256(5) -0.0062(4) 0.0019(4) -0.0075(4)
O4 0.0473(6) 0.0356(6) 0.0385(6) -0.0167(4) 0.0094(5) -0.0123(5)
O5 0.0556(7) 0.0292(5) 0.0313(6) -0.0002(4) -0.0048(5) -0.0067(5)
O6 0.0409(6) 0.0284(5) 0.0249(5) -0.0051(4) 0.0050(4) -0.0092(4)
C1 0.0422(8) 0.0229(6) 0.0345(7) -0.0088(5) 0.0019(6) -0.0101(6)
C2 0.0309(7) 0.0254(7) 0.0331(7) -0.0064(5) 0.0012(6) -0.0024(5)
C3 0.0267(7) 0.0297(7) 0.0309(7) -0.0066(5) 0.0005(5) -0.0085(5)
C4 0.0266(7) 0.0241(6) 0.0259(7) -0.0063(5) 0.0012(5) -0.0085(5)
C5 0.0351(7) 0.0267(7) 0.0349(7) -0.0086(5) -0.0005(6) -0.0135(6)
C6 0.0409(8) 0.0226(6) 0.0326(7) -0.0068(5) 0.0025(6) -0.0096(6)
C7 0.0329(7) 0.0273(7) 0.0343(8) -0.0043(6) -0.0042(6) -0.0040(5)
C8 0.0305(7) 0.0304(7) 0.0331(7) -0.0062(5) -0.0051(6) -0.0102(6)
C9 0.0304(7) 0.0239(6) 0.0230(6) -0.0045(5) 0.0006(5) -0.0104(5)
C10 0.0357(7) 0.0261(7) 0.0306(7) -0.0080(5) 0.0006(6) -0.0138(6)

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

# 10. 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
O1W H2W 0.80(2) . ?
O1W H1W 0.82(3) . ?
O1 C1 1.4349(17) . ?
O1 H1O 0.8200 . ?
O2 C2 1.4369(17) . ?
O2 H2O 0.8200 . ?
O3 C4 1.4460(15) . ?
O3 H3O 0.8200 . ?
O4 C6 1.4363(17) . ?
O4 H4O 0.8200 . ?
O5 C7 1.4356(17) . ?
O5 H5O 0.8200 . ?
O6 C9 1.4483(15) . ?
O6 H6O 0.8200 . ?
C1 H1 0.9800 . ?
C2 C1 1.530(2) . ?
C2 H2 0.9800 . ?
C3 C2 1.5215(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C3 1.5287(18) . ?
C4 C5 1.5316(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.527(2) . ?
C6 C10 1.529(2) . ?
C6 H6 0.9800 . ?
C7 H7 0.9800 . ?
C8 C9 1.5234(19) . ?
C8 C7 1.5266(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
O1 C1 C2 108.54(12) . . ?
O1 C1 H1 107.8 . . ?
O2 C2 C1 110.58(11) . . ?
O2 C2 C3 107.01(11) . . ?
O2 C2 H2 108.9 . . ?
O3 C4 C3 110.37(10) . . ?
O3 C4 C5 105.97(10) . . ?
O4 C6 C7 106.03(12) . . ?
O4 C6 C10 111.10(11) . . ?
O4 C6 H6 109.2 . . ?
O5 C7 C6 110.20(12) . . ?
O5 C7 C8 111.93(11) . . ?
O5 C7 H7 107.7 . . ?
O6 C9 C8 105.74(10) . . ?
C1 O1 H1O 109.5 . . ?
C1 C2 H2 108.9 . . ?
C2 C3 C4 112.86(11) . . ?
C2 O2 H2O 109.5 . . ?
C2 C1 H1 107.8 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C3 C2 C1 112.49(11) . . ?
C3 C4 C5 111.65(11) . . ?
C3 C2 H2 108.9 . . ?
C4 O3 H3O 109.5 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 O4 H4O 109.5 . . ?
C6 C7 H7 107.7 . . ?
C6 C10 H10A 109.1 . . ?
C6 C10 H10B 109.1 . . ?
C7 C6 C10 112.11(11) . . ?
C7 O5 H5O 109.5 . . ?
C7 C6 H6 109.2 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C8 C7 C6 111.45(11) . . ?
C8 C7 H7 107.7 . . ?
C9 C8 C7 113.30(11) . . ?
C9 O6 H6O 109.5 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C10 C6 H6 109.2 . . ?
H3A C3 H3B 107.8 . . ?
H5A C5 H5B 107.8 . . ?
H8A C8 H8B 107.7 . . ?
H10A C10 H10B 107.8 . . ?
H2W O1W H1W 105(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
O2 C2 C1 O1 -165.68(10) . . . . ?
O3 C4 C3 C2 64.25(14) . . . . ?
O4 C6 C7 O5 165.25(10) . . . . ?
O4 C6 C7 C8 -69.85(14) . . . . ?
C3 C2 C1 O1 74.74(13) . . . . ?
C4 C3 C2 O2 -69.27(14) . . . . ?
C4 C3 C2 C1 52.37(15) . . . . ?
C5 C4 C3 C2 -178.17(11) . . . . ?
C7 C8 C9 O6 -61.40(13) . . . . ?
C9 C8 C7 O5 70.56(15) . . . . ?
C9 C8 C7 C6 -53.36(16) . . . . ?
C10 C6 C7 O5 -73.34(14) . . . . ?
C10 C6 C7 C8 51.56(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# D H A D - H H...A D...A D - H...A symm(A)
# - - - ----- ----- ----- --------- -------
O1 H1O O3 0.82 2.01 2.7086(17) 142 2_666 yes
O2 H2O O5 0.82 1.88 2.7010(18) 174 1_545 yes
O3 H3O O2 0.82 2.00 2.7205(17) 147 1_555 yes
O4 H4O O1W 0.82 1.89 2.688(2) 164 1_556 yes
O5 H5O O6 0.82 2.03 2.7157(17) 141 1_555 yes
O6 H6O O4 0.82 2.00 2.7282(18) 148 2_767 yes
O1W H1W O2 0.82(3) 2.05(3) 2.856(3) 167.15(2) 2_766 yes
O1W H2W O1 0.81(3) 1.97(3) 2.757(2) 165.88(2) 1_565 yes

#===END


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

data_beta_polymorph
_database_code_depnum_ccdc_archive 'CCDC 620927'

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
all trans-perhydro-2,3,4a,6,7,8a-naphthalenehexaol
;
_chemical_name_common            
'all trans-perhydro-2,3,4a,6,7,8a-naphthalenehexaol'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H18 O6'
_chemical_formula_structural     ?
_chemical_formula_sum            'C10 H18 O6'
_chemical_formula_weight         234.24
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   6.5273(14)
_cell_length_b                   5.9589(12)
_cell_length_c                   13.166(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.163(3)
_cell_angle_gamma                90
_cell_volume                     512.10(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_special_details            
; ?
;

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.125
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_T_max  0.9925

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoKa
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_reflns_number            3602
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000

_diffrn_reflns_reduction_process 
;
?
;

_reflns_number_total             953
_reflns_number_gt                839
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

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

# 8. REFINEMENT DATA

_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^)+(0.0332P)^2^+0.1421P] 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         953
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT 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
O1 O 0.19346(16) 0.64527(17) 0.88185(8) 0.0324(3) Uani 1 1 d . . .
O2 O 0.59290(17) 0.98418(19) 0.75996(8) 0.0358(3) Uani 1 1 d . . .
O3 O 0.68981(15) 1.18626(15) 0.93925(7) 0.0269(3) Uani 1 1 d . . .
C1 C 0.2856(2) 0.8471(2) 0.84360(11) 0.0262(3) Uani 1 1 d . . .
C2 C 0.5112(2) 0.8031(2) 0.81919(11) 0.0270(4) Uani 1 1 d . . .
C3 C 0.6406(2) 0.7844(2) 0.91490(11) 0.0250(3) Uani 1 1 d . . .
C4 C 0.6150(2) 0.9831(2) 0.98678(11) 0.0221(3) Uani 1 1 d . . .
C5 C 0.7399(2) 0.9554(2) 1.08398(11) 0.0241(3) Uani 1 1 d . . .
H1O H 0.1988 0.6453 0.9441 0.049 Uiso 1 1 calc R . .
H2O H 0.5166 1.0095 0.7117 0.054 Uiso 1 1 calc R . .
H3O H 0.6821 1.1736 0.8773 0.040 Uiso 1 1 calc R . .
H1 H 0.2161 0.8857 0.7799 0.031 Uiso 1 1 calc R . .
H2 H 0.5223 0.6632 0.7804 0.032 Uiso 1 1 calc R . .
H3A H 0.7836 0.7725 0.8958 0.030 Uiso 1 1 calc R . .
H3B H 0.6037 0.6478 0.9505 0.030 Uiso 1 1 calc R . .
H5A H 0.6977 0.8187 1.1180 0.029 Uiso 1 1 calc R . .
H5B H 0.8836 0.9402 1.0666 0.029 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
O1 0.0361(6) 0.0308(6) 0.0302(6) -0.0017(5) -0.0027(5) -0.0091(5)
O2 0.0346(7) 0.0482(7) 0.0244(6) 0.0064(5) -0.0011(5) -0.0067(5)
O3 0.0318(6) 0.0261(6) 0.0228(6) 0.0030(4) 0.0002(4) -0.0045(4)
C1 0.0265(7) 0.0283(8) 0.0238(8) 0.0021(7) -0.0058(6) -0.0012(6)
C2 0.0307(8) 0.0269(8) 0.0236(8) -0.0035(6) 0.0006(6) -0.0008(6)
C3 0.0218(7) 0.0254(8) 0.0277(8) -0.0005(6) 0.0008(6) 0.0030(6)
C4 0.0232(8) 0.0197(7) 0.0234(8) 0.0016(6) -0.0007(6) 0.0009(5)
C5 0.0203(7) 0.0250(7) 0.0270(8) 0.0038(6) -0.0010(6) 0.0016(6)

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

# 10. 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
O1 C1 1.4366(17) . ?
O1 H1O 0.8200 . ?
O2 C2 1.4353(17) . ?
O2 H2O 0.8200 . ?
O3 C4 1.4481(16) . ?
O3 H3O 0.8200 . ?
C1 H1 0.9800 . ?
C2 C1 1.530(2) . ?
C2 H2 0.9800 . ?
C3 C2 1.519(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.524(2) . ?
C4 C3 1.5255(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?

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
O1 C1 C2 109.51(11) . . ?
O1 C1 H1 107.7 . . ?
O2 C2 C1 110.15(12) . . ?
O2 C2 C3 107.41(12) . . ?
O2 C2 H2 109.1 . . ?
O3 C4 C3 110.07(11) . . ?
O3 C4 C5 105.86(11) . . ?
C1 O1 H1O 109.5 . . ?
C1 C2 H2 109.1 . . ?
C2 O2 H2O 109.5 . . ?
C2 C3 C4 113.33(11) . . ?
C2 C1 H1 107.7 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C3 C2 C1 111.80(12) . . ?
C3 C2 H2 109.1 . . ?
C4 O3 H3O 109.5 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C5 C4 C3 112.18(11) . . ?
H3A C3 H3B 107.7 . . ?
H5A C5 H5B 107.8 . . ?

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
O2 C2 C1 O1 166.84(11) . . . . ?
O3 C4 C3 C2 -64.71(15) . . . . ?
C3 C2 C1 O1 -73.82(14) . . . . ?
C4 C3 C2 O2 68.32(15) . . . . ?
C4 C3 C2 C1 -52.62(16) . . . . ?
C5 C4 C3 C2 177.70(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# D H A D - H H...A D...A D - H...A symm(A)
# - - - ----- ----- ----- --------- -------
O1 H1O O3 0.82 1.97 2.6695(15) 142 3_677 yes
O2 H2O O1 0.82 2.01 2.8074(16) 164 2_556 yes
O3 H3O O2 0.82 2.00 2.7228(15) 147 1_555 yes

