# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Lars Ohrstrom'
_publ_contact_author_email       OHRSTROM@CHALMERS.SE

_publ_section_title              
;
Network analysis of bicyclo[3.3.1]nonanes: the diol,
the dione and the acetal
;
loop_
_publ_author_name
'Lars Ohrstrom'
'Eugenius Butkus'
'Magnus T. Johnson'
'Edvinas Orentas'
'Carl-Johan Wallentin'
;
K.Warnmark
;
'Ola Wendt'

# Attachment 'wallentincomp2.CIF'

data_compound2
_database_code_depnum_ccdc_archive 'CCDC 717098'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration unk
_chemical_formula_sum            'C9 H16 O2'
_chemical_formula_weight         156.2242

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(1)2(1)2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'-y, -x, -z+1/2'
'y, x, -z'
'y+1/2, -x+1/2, z+3/4'
'-y+1/2, x+1/2, z+1/4'

_cell_length_a                   9.9192(4)
_cell_length_b                   9.9192(4)
_cell_length_c                   17.2456(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1696.80(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4996
_cell_measurement_theta_min      2.3651
_cell_measurement_theta_max      32.7488

_exptl_crystal_description       octahedron
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur 3'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1829
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10328
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.03
_reflns_number_total             934
_reflns_number_gt                850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0805P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         934
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_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 0.53474(14) 0.18475(16) 0.30869(7) 0.0612(5) Uani 1 1 d . . .
H1 H 0.5818 0.1315 0.2844 0.092 Uiso 1 1 calc R . .
O2 O -0.01688(14) 0.30419(18) 0.28080(8) 0.0622(5) Uani 1 1 d . . .
H2 H 0.0045 0.3068 0.3267 0.093 Uiso 1 1 calc R . .
C3 C 0.08626(19) 0.23641(19) 0.23748(10) 0.0454(5) Uani 1 1 d . . .
H3 H 0.0408 0.1889 0.1951 0.055 Uiso 1 1 calc R . .
C4 C 0.3698(2) 0.3594(2) 0.30313(11) 0.0535(6) Uani 1 1 d . . .
H4A H 0.4294 0.4271 0.3249 0.064 Uiso 1 1 calc R . .
H4B H 0.3280 0.3116 0.3459 0.064 Uiso 1 1 calc R . .
C5 C 0.36933(19) 0.16884(18) 0.20266(9) 0.0426(5) Uani 1 1 d . . .
H5 H 0.4318 0.1180 0.1698 0.051 Uiso 1 1 calc R . .
C6 C 0.45328(18) 0.2601(2) 0.25581(11) 0.0466(5) Uani 1 1 d . . .
H6 H 0.5141 0.3127 0.2228 0.056 Uiso 1 1 calc R . .
C7 C 0.1837(2) 0.33759(19) 0.19964(9) 0.0476(5) Uani 1 1 d . . .
H7 H 0.1307 0.3950 0.1649 0.057 Uiso 1 1 calc R . .
C8 C 0.2837(2) 0.25859(19) 0.14988(10) 0.0533(6) Uani 1 1 d . . .
H8A H 0.3413 0.3205 0.1216 0.064 Uiso 1 1 calc R . .
H8B H 0.2355 0.2035 0.1126 0.064 Uiso 1 1 calc R . .
C9 C 0.15672(19) 0.1293(2) 0.28603(10) 0.0496(5) Uani 1 1 d . . .
H9A H 0.0928 0.0584 0.2983 0.059 Uiso 1 1 calc R . .
H9B H 0.1862 0.1693 0.3344 0.059 Uiso 1 1 calc R . .
C10 C 0.2596(2) 0.4299(2) 0.25564(14) 0.0566(6) Uani 1 1 d . . .
H10A H 0.1952 0.4700 0.2911 0.068 Uiso 1 1 calc R . .
H10B H 0.3005 0.5024 0.2262 0.068 Uiso 1 1 calc R . .
C11 C 0.2786(2) 0.06706(19) 0.24484(12) 0.0517(5) Uani 1 1 d . . .
H11A H 0.2465 0.0014 0.2075 0.062 Uiso 1 1 calc R . .
H11B H 0.3326 0.0192 0.2828 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
O1 0.0586(9) 0.0776(11) 0.0473(8) -0.0150(7) -0.0099(7) 0.0273(8)
O2 0.0495(8) 0.0852(11) 0.0520(8) 0.0069(8) 0.0012(6) 0.0243(8)
C3 0.0434(10) 0.0537(12) 0.0391(10) -0.0026(9) -0.0056(8) 0.0081(9)
C4 0.0502(11) 0.0480(11) 0.0623(12) -0.0174(10) -0.0095(10) 0.0032(9)
C5 0.0500(11) 0.0478(11) 0.0301(9) -0.0050(8) 0.0041(8) 0.0126(9)
C6 0.0448(11) 0.0496(11) 0.0454(10) -0.0011(9) 0.0008(9) 0.0067(9)
C7 0.0538(11) 0.0516(12) 0.0373(9) 0.0127(8) -0.0041(9) 0.0145(9)
C8 0.0567(12) 0.0710(14) 0.0323(9) 0.0060(8) 0.0026(9) 0.0116(10)
C9 0.0517(12) 0.0457(11) 0.0513(11) 0.0072(9) 0.0021(10) -0.0014(8)
C10 0.0568(13) 0.0395(10) 0.0736(13) -0.0008(10) -0.0032(12) 0.0070(9)
C11 0.0608(13) 0.0397(10) 0.0545(11) -0.0050(9) -0.0016(10) 0.0075(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
O1 C6 1.430(2) . ?
O1 H1 0.8200 . ?
O2 C3 1.434(2) . ?
O2 H2 0.8200 . ?
C3 C9 1.523(3) . ?
C3 C7 1.538(3) . ?
C3 H3 0.9800 . ?
C4 C6 1.523(3) . ?
C4 C10 1.535(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C8 1.530(2) . ?
C5 C6 1.534(2) . ?
C5 C11 1.535(3) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 C8 1.528(3) . ?
C7 C10 1.529(3) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.532(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 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
C6 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
O2 C3 C9 111.60(14) . . ?
O2 C3 C7 111.29(15) . . ?
C9 C3 C7 113.60(15) . . ?
O2 C3 H3 106.6 . . ?
C9 C3 H3 106.6 . . ?
C7 C3 H3 106.6 . . ?
C6 C4 C10 113.32(15) . . ?
C6 C4 H4A 108.9 . . ?
C10 C4 H4A 108.9 . . ?
C6 C4 H4B 108.9 . . ?
C10 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C8 C5 C6 108.25(14) . . ?
C8 C5 C11 109.83(16) . . ?
C6 C5 C11 115.03(15) . . ?
C8 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C11 C5 H5 107.8 . . ?
O1 C6 C4 107.66(14) . . ?
O1 C6 C5 112.29(15) . . ?
C4 C6 C5 114.00(15) . . ?
O1 C6 H6 107.5 . . ?
C4 C6 H6 107.5 . . ?
C5 C6 H6 107.5 . . ?
C8 C7 C10 109.97(17) . . ?
C8 C7 C3 108.16(15) . . ?
C10 C7 C3 115.60(15) . . ?
C8 C7 H7 107.6 . . ?
C10 C7 H7 107.6 . . ?
C3 C7 H7 107.6 . . ?
C7 C8 C5 108.94(13) . . ?
C7 C8 H8A 109.9 . . ?
C5 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
C5 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C3 C9 C11 112.86(14) . . ?
C3 C9 H9A 109.0 . . ?
C11 C9 H9A 109.0 . . ?
C3 C9 H9B 109.0 . . ?
C11 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C7 C10 C4 114.52(15) . . ?
C7 C10 H10A 108.6 . . ?
C4 C10 H10A 108.6 . . ?
C7 C10 H10B 108.6 . . ?
C4 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C9 C11 C5 114.66(15) . . ?
C9 C11 H11A 108.6 . . ?
C5 C11 H11A 108.6 . . ?
C9 C11 H11B 108.6 . . ?
C5 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.028

# Attachment 'wallentincomp4.CIF'

data_compound4
_database_code_depnum_ccdc_archive 'CCDC 722431'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 O4'
_chemical_formula_weight         240.29

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.4565(6)
_cell_length_b                   7.9243(4)
_cell_length_c                   13.7482(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.287(6)
_cell_angle_gamma                90.00
_cell_volume                     1198.04(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2405
_cell_measurement_theta_min      2.5660
_cell_measurement_theta_max      33.1056

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_min  0.81094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur 3'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1829
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7626
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2187
_reflns_number_gt                1261
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2187
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.44474(13) 0.24402(17) 0.02657(10) 0.0529(4) Uani 1 1 d . . .
O2 O 0.42474(14) -0.20880(19) 0.33638(12) 0.0677(5) Uani 1 1 d . . .
O3 O 0.44270(14) 0.42468(17) 0.15201(11) 0.0568(4) Uani 1 1 d . . .
O4 O 0.62345(13) -0.13569(19) 0.39271(11) 0.0609(5) Uani 1 1 d . . .
C5 C 0.46153(18) 0.2520(2) 0.13370(14) 0.0429(5) Uani 1 1 d . . .
C6 C 0.51104(18) -0.0879(2) 0.32251(15) 0.0450(5) Uani 1 1 d . . .
C7 C 0.51824(18) -0.0957(2) 0.21333(15) 0.0452(5) Uani 1 1 d . . .
H7 H 0.5350 -0.2127 0.1985 0.054 Uiso 1 1 calc R . .
C8 C 0.59228(19) 0.2063(2) 0.18768(16) 0.0516(6) Uani 1 1 d . . .
H8A H 0.6122 0.2498 0.2563 0.062 Uiso 1 1 calc R . .
H8B H 0.6453 0.2614 0.1535 0.062 Uiso 1 1 calc R . .
C9 C 0.36880(17) 0.1378(2) 0.16198(14) 0.0448(5) Uani 1 1 d . . .
H9 H 0.2881 0.1662 0.1176 0.054 Uiso 1 1 calc R . .
C10 C 0.39530(19) -0.0459(2) 0.14220(15) 0.0495(6) Uani 1 1 d . . .
H10A H 0.3321 -0.1183 0.1537 0.059 Uiso 1 1 calc R . .
H10B H 0.3965 -0.0594 0.0724 0.059 Uiso 1 1 calc R . .
C11 C 0.4730(2) 0.0826(3) 0.35195(16) 0.0573(6) Uani 1 1 d . . .
H11A H 0.5410 0.1600 0.3626 0.069 Uiso 1 1 calc R . .
H11B H 0.4524 0.0721 0.4155 0.069 Uiso 1 1 calc R . .
C12 C 0.61787(19) 0.0174(3) 0.19196(16) 0.0520(6) Uani 1 1 d . . .
H12A H 0.6933 -0.0031 0.2442 0.062 Uiso 1 1 calc R . .
H12B H 0.6302 -0.0168 0.1278 0.062 Uiso 1 1 calc R . .
C13 C 0.3646(2) 0.1555(3) 0.27219(15) 0.0574(6) Uani 1 1 d . . .
H13A H 0.3581 0.2744 0.2866 0.069 Uiso 1 1 calc R . .
H13B H 0.2914 0.1006 0.2786 0.069 Uiso 1 1 calc R . .
C14 C 0.3555(2) 0.3660(3) -0.01899(16) 0.0609(6) Uani 1 1 d . . .
H14A H 0.2770 0.3128 -0.0470 0.073 Uiso 1 1 calc R . .
H14B H 0.3780 0.4251 -0.0728 0.073 Uiso 1 1 calc R . .
C15 C 0.3513(2) 0.4856(3) 0.06502(17) 0.0633(7) Uani 1 1 d . . .
H15A H 0.3694 0.6000 0.0486 0.076 Uiso 1 1 calc R . .
H15B H 0.2718 0.4840 0.0770 0.076 Uiso 1 1 calc R . .
C16 C 0.6169(2) -0.3091(3) 0.4122(2) 0.0744(8) Uani 1 1 d . . .
H16A H 0.6551 -0.3333 0.4832 0.089 Uiso 1 1 calc R . .
H16B H 0.6572 -0.3745 0.3714 0.089 Uiso 1 1 calc R . .
C17 C 0.4863(2) -0.3492(3) 0.38503(19) 0.0738(8) Uani 1 1 d . . .
H17A H 0.4689 -0.4466 0.3405 0.089 Uiso 1 1 calc R . .
H17B H 0.4616 -0.3744 0.4454 0.089 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 0.0658(11) 0.0538(9) 0.0439(9) 0.0062(7) 0.0236(8) 0.0124(7)
O2 0.0463(10) 0.0745(11) 0.0816(11) 0.0342(9) 0.0169(9) -0.0031(8)
O3 0.0704(11) 0.0433(9) 0.0561(9) -0.0017(7) 0.0166(8) 0.0064(7)
O4 0.0438(10) 0.0690(10) 0.0615(10) 0.0171(8) 0.0011(8) -0.0021(8)
C5 0.0470(13) 0.0408(12) 0.0424(12) 0.0010(9) 0.0150(10) 0.0020(10)
C6 0.0350(12) 0.0510(13) 0.0461(13) 0.0095(9) 0.0066(10) -0.0036(10)
C7 0.0483(13) 0.0426(12) 0.0459(13) -0.0003(9) 0.0151(10) 0.0017(10)
C8 0.0410(14) 0.0530(14) 0.0620(14) 0.0061(10) 0.0167(11) -0.0061(10)
C9 0.0324(12) 0.0567(13) 0.0447(13) 0.0062(10) 0.0101(10) 0.0029(10)
C10 0.0492(14) 0.0525(13) 0.0444(12) 0.0007(10) 0.0090(11) -0.0095(11)
C11 0.0623(16) 0.0686(15) 0.0435(13) 0.0025(11) 0.0190(12) 0.0036(12)
C12 0.0431(13) 0.0616(14) 0.0552(13) 0.0057(11) 0.0201(11) 0.0060(11)
C13 0.0580(15) 0.0659(14) 0.0567(14) 0.0099(11) 0.0298(12) 0.0128(12)
C14 0.0667(16) 0.0613(14) 0.0540(14) 0.0131(12) 0.0159(13) 0.0132(13)
C15 0.0705(17) 0.0581(14) 0.0633(15) 0.0119(12) 0.0217(14) 0.0197(13)
C16 0.0613(18) 0.0663(17) 0.095(2) 0.0248(14) 0.0219(15) 0.0133(13)
C17 0.077(2) 0.0622(16) 0.0766(18) 0.0171(13) 0.0124(15) -0.0063(14)

_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 1.418(2) . ?
O1 C5 1.432(2) . ?
O2 C17 1.385(3) . ?
O2 C6 1.428(2) . ?
O3 C5 1.418(2) . ?
O3 C15 1.434(2) . ?
O4 C16 1.406(3) . ?
O4 C6 1.427(2) . ?
C5 C8 1.517(3) . ?
C5 C9 1.527(3) . ?
C6 C11 1.509(3) . ?
C6 C7 1.527(3) . ?
C7 C10 1.524(3) . ?
C7 C12 1.543(3) . ?
C7 H7 0.9800 . ?
C8 C12 1.523(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.528(3) . ?
C9 C13 1.536(3) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.522(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.505(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.471(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 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
C14 O1 C5 107.22(14) . . ?
C17 O2 C6 109.02(17) . . ?
C5 O3 C15 106.77(15) . . ?
C16 O4 C6 107.58(16) . . ?
O3 C5 O1 104.01(14) . . ?
O3 C5 C8 108.79(15) . . ?
O1 C5 C8 108.78(16) . . ?
O3 C5 C9 112.03(16) . . ?
O1 C5 C9 109.47(16) . . ?
C8 C5 C9 113.32(16) . . ?
O2 C6 O4 105.00(15) . . ?
O2 C6 C11 107.57(17) . . ?
O4 C6 C11 109.28(17) . . ?
O2 C6 C7 109.52(17) . . ?
O4 C6 C7 111.51(16) . . ?
C11 C6 C7 113.54(16) . . ?
C10 C7 C6 108.97(16) . . ?
C10 C7 C12 109.10(16) . . ?
C6 C7 C12 114.21(17) . . ?
C10 C7 H7 108.1 . . ?
C6 C7 H7 108.1 . . ?
C12 C7 H7 108.1 . . ?
C5 C8 C12 113.99(17) . . ?
C5 C8 H8A 108.8 . . ?
C12 C8 H8A 108.8 . . ?
C5 C8 H8B 108.8 . . ?
C12 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C5 C9 C10 109.42(16) . . ?
C5 C9 C13 114.45(17) . . ?
C10 C9 C13 108.99(16) . . ?
C5 C9 H9 107.9 . . ?
C10 C9 H9 107.9 . . ?
C13 C9 H9 107.9 . . ?
C7 C10 C9 109.06(15) . . ?
C7 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C7 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C6 C11 C13 112.68(18) . . ?
C6 C11 H11A 109.1 . . ?
C13 C11 H11A 109.1 . . ?
C6 C11 H11B 109.1 . . ?
C13 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C8 C12 C7 115.70(17) . . ?
C8 C12 H12A 108.4 . . ?
C7 C12 H12A 108.4 . . ?
C8 C12 H12B 108.4 . . ?
C7 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
C11 C13 C9 115.55(17) . . ?
C11 C13 H13A 108.4 . . ?
C9 C13 H13A 108.4 . . ?
C11 C13 H13B 108.4 . . ?
C9 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
O1 C14 C15 105.34(17) . . ?
O1 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
O1 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
O3 C15 C14 104.75(17) . . ?
O3 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
O3 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
O4 C16 C17 105.55(19) . . ?
O4 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
O4 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
O2 C17 C16 107.01(19) . . ?
O2 C17 H17A 110.3 . . ?
C16 C17 H17A 110.3 . . ?
O2 C17 H17B 110.3 . . ?
C16 C17 H17B 110.3 . . ?
H17A C17 H17B 108.6 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.059


# Attachment 'wallentincomp3.cif'

data_compound3
_database_code_depnum_ccdc_archive 'CCDC 722432'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration rm
_chemical_formula_sum            'C9 H12 O2'
_chemical_formula_weight         152.19

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   P6(1)22

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'y, x, -z+1/3'
'-y, -x, -z+5/6'
'x, x-y, -z+1/6'
'-x+y, y, -z+1/2'

_cell_length_a                   6.9851(4)
_cell_length_b                   6.9851(4)
_cell_length_c                   29.362(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1240.68(17)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    612
_cell_measurement_theta_min      2.7636
_cell_measurement_theta_max      33.0260

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_min  0.67090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur 3'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1829
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3972
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         24.99
_reflns_number_total             513
_reflns_number_gt                218
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         513
_refine_ls_number_parameters     51
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.7961(4) 0.2935(4) 0.18002(8) 0.1404(11) Uani 1 1 d . . .
C3 C 0.6283(6) 0.3838(6) 0.12144(11) 0.0982(11) Uani 1 1 d . . .
H3 H 0.5314 0.3782 0.1462 0.118 Uiso 1 1 calc R . .
C4 C 0.7734(6) 0.3021(5) 0.13964(11) 0.0856(10) Uani 1 1 d . . .
C5 C 0.4851(7) 0.2426(4) 0.0833 0.1094(16) Uani 1 2 d S . .
H5A H 0.3912 0.0924 0.0940 0.131 Uiso 0.50 1 calc PR . .
H5B H 0.3912 0.2988 0.0727 0.131 Uiso 0.50 1 calc PR . .
C1 C 0.8861(5) 0.6503(5) 0.06147(13) 0.1024(10) Uani 1 1 d . . .
H1A H 0.9184 0.7895 0.0477 0.123 Uiso 1 1 calc R . .
H1B H 1.0260 0.6612 0.0694 0.123 Uiso 1 1 calc R . .
C2 C 0.7558(7) 0.6185(6) 0.10461(12) 0.1220(13) Uani 1 1 d . . .
H2A H 0.8571 0.7094 0.1284 0.146 Uiso 1 1 calc R . .
H2B H 0.6529 0.6712 0.0994 0.146 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 0.159(2) 0.147(2) 0.0648(15) 0.0117(14) -0.0302(15) 0.0386(14)
C3 0.138(3) 0.115(3) 0.071(3) 0.005(2) 0.029(2) 0.084(3)
C4 0.103(3) 0.074(2) 0.066(2) 0.0038(19) -0.011(2) 0.0346(19)
C5 0.091(4) 0.120(3) 0.108(4) 0.038(3) 0.000 0.0453(18)
C1 0.110(3) 0.068(2) 0.126(3) 0.025(2) 0.013(3) 0.042(2)
C2 0.192(4) 0.097(3) 0.105(3) -0.008(2) -0.004(3) 0.093(3)

_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 C4 1.202(3) . ?
C3 C4 1.489(4) . ?
C3 C5 1.496(3) . ?
C3 C2 1.505(4) . ?
C3 H3 0.9800 . ?
C4 C1 1.491(4) 11 ?
C5 C3 1.496(3) 11 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 C4 1.491(4) 11 ?
C1 C2 1.510(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 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
C4 C3 C5 112.0(2) . . ?
C4 C3 C2 112.9(3) . . ?
C5 C3 C2 108.0(3) . . ?
C4 C3 H3 107.9 . . ?
C5 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
O1 C4 C3 120.4(4) . . ?
O1 C4 C1 123.4(4) . 11 ?
C3 C4 C1 116.2(3) . 11 ?
C3 C5 C3 109.3(3) 11 . ?
C3 C5 H5A 109.8 11 . ?
C3 C5 H5A 109.8 . . ?
C3 C5 H5B 109.8 11 . ?
C3 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
C4 C1 C2 114.8(3) 11 . ?
C4 C1 H1A 108.6 11 . ?
C2 C1 H1A 108.6 . . ?
C4 C1 H1B 108.6 11 . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C1 114.9(3) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.061
_refine_diff_density_min         -0.082
_refine_diff_density_rms         0.021

