# 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 \w-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 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^)+(0.0805P)^2^+0.0000P] 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 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 \w-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 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^)+(0.0600P)^2^+0.0000P] 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 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 \w-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 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^)+(0.0300P)^2^+0.0000P] 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 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