# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ; ? ; _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_volume ? _journal_year ? _publ_author_address ; Chemistry Section, M313, School of Biomedical and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; _publ_contact_author_address ; Chemistry Section, M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; _publ_contact_author_email simon.grabowsky@uwa.edu.au _publ_contact_author_fax '+618 6488 1005' _publ_contact_author_phone '+618 6488 3515' #TrackingRef 'ppa.cif' # 1. SUBMISSION DETAILS _publ_contact_author_name 'Dr. Simon Grabowsky' _publ_contact_letter ; ; _publ_requested_coeditor_name ? # 3. TITLE AND AUTHOR LIST _publ_section_title ; Crystal packing in the 2-R,4-oxo-[1,3-a/b]-napthodioxanes - Hirshfeld surface analysis and melting point correlation ; loop_ _publ_author_name P.M.Dean S.Grabowsky B.W.Skelton A.N.Sobolev M.A.Spackman ; A.H.White ; data_ppa _database_code_depnum_ccdc_archive 'CCDC 846987' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 O5' _chemical_formula_sum 'C17 H16 O5' _chemical_formula_weight 300.30 _chemical_absolute_configuration unk 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.6142(2) _cell_length_b 5.8945(1) _cell_length_c 11.1109(2) _cell_angle_alpha 90.0 _cell_angle_beta 90.093(2) _cell_angle_gamma 90.0 _cell_volume 695.16(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13645 _cell_measurement_theta_min 3.91 _cell_measurement_theta_max 37.33 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method ? _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99367 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25466 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 37.38 _reflns_number_total 6986 _reflns_number_gt 6072 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0590P)^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 constr _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 ? _refine_ls_number_reflns 3793 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0843 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.08752(6) 0.79311(13) 0.27234(6) 0.01456(12) Uani 1 1 d . . . C2 C -0.02724(9) 0.69524(17) 0.23586(8) 0.01366(15) Uani 1 1 d . . . H2 H -0.0159 0.6102 0.1588 0.016 Uiso 1 1 calc R . . O3 O -0.07814(6) 0.54835(14) 0.32707(6) 0.01574(13) Uani 1 1 d . . . O4 O -0.04553(7) 0.24465(14) 0.43928(7) 0.01866(15) Uani 1 1 d . . . C4 C 0.00006(8) 0.39313(17) 0.37832(8) 0.01378(15) Uani 1 1 d . . . C5 C 0.13588(8) 0.42483(16) 0.35447(8) 0.01271(15) Uani 1 1 d . . . C6 C 0.22332(9) 0.26380(17) 0.38785(8) 0.01361(15) Uani 1 1 d . . . H6 H 0.1964 0.1275 0.4254 0.016 Uiso 1 1 calc R . . C7 C 0.35333(8) 0.30075(17) 0.36632(8) 0.01271(14) Uani 1 1 d . . . C8 C 0.44628(9) 0.13712(17) 0.39768(9) 0.01556(16) Uani 1 1 d . . . H8 H 0.4216 0.0000 0.4359 0.019 Uiso 1 1 calc R . . C9 C 0.57146(9) 0.17522(18) 0.37327(9) 0.01703(17) Uani 1 1 d . . . H9 H 0.6325 0.0635 0.3934 0.020 Uiso 1 1 calc R . . C10 C 0.60959(9) 0.38075(19) 0.31815(9) 0.01673(17) Uani 1 1 d . . . H10 H 0.6963 0.4061 0.3018 0.020 Uiso 1 1 calc R . . C11 C 0.52259(8) 0.54360(18) 0.28819(9) 0.01497(16) Uani 1 1 d . . . H11 H 0.5496 0.6809 0.2517 0.018 Uiso 1 1 calc R . . C12 C 0.39225(8) 0.50834(16) 0.31141(8) 0.01249(15) Uani 1 1 d . . . C13 C 0.30097(8) 0.67282(16) 0.27944(8) 0.01326(15) Uani 1 1 d . . . H13 H 0.3263 0.8117 0.2435 0.016 Uiso 1 1 calc R . . C14 C 0.17599(8) 0.63083(16) 0.30054(8) 0.01270(15) Uani 1 1 d . . . C15 C -0.12361(9) 0.88351(18) 0.21983(9) 0.01487(16) Uani 1 1 d . . . H15 H -0.1415 0.9581 0.2988 0.018 Uiso 1 1 calc R . . C16 C -0.08680(10) 1.05974(19) 0.12654(9) 0.01818(18) Uani 1 1 d . . . H161 H -0.1271 1.2078 0.1434 0.022 Uiso 1 1 calc R . . H162 H 0.0057 1.0802 0.1236 0.022 Uiso 1 1 calc R . . O17 O -0.13359(7) 0.96291(15) 0.01693(7) 0.01823(14) Uani 1 1 d . . . C18 C -0.24999(9) 0.85738(18) 0.04792(9) 0.01502(16) Uani 1 1 d . . . O19 O -0.23588(6) 0.78608(15) 0.17152(6) 0.01770(14) Uani 1 1 d . . . C20 C -0.35948(10) 1.0225(2) 0.04041(10) 0.02051(19) Uani 1 1 d . . . H201 H -0.3431 1.1524 0.0932 0.031 Uiso 1 1 calc R . . H202 H -0.4370 0.9463 0.0659 0.031 Uiso 1 1 calc R . . H203 H -0.3690 1.0753 -0.0427 0.031 Uiso 1 1 calc R . . C21 C -0.26827(11) 0.6516(2) -0.03126(11) 0.0235(2) Uani 1 1 d . . . H211 H -0.1953 0.5507 -0.0232 0.035 Uiso 1 1 calc R . . H212 H -0.2767 0.6998 -0.1153 0.035 Uiso 1 1 calc R . . H213 H -0.3447 0.5707 -0.0066 0.035 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 0.0107(3) 0.0132(3) 0.0197(3) 0.0014(3) -0.0018(2) -0.0017(2) C2 0.0116(3) 0.0156(4) 0.0138(4) 0.0011(3) -0.0008(3) -0.0029(3) O3 0.0115(3) 0.0187(3) 0.0170(3) 0.0046(3) -0.0001(2) -0.0027(2) O4 0.0170(3) 0.0194(3) 0.0196(3) 0.0037(3) 0.0023(2) -0.0048(3) C4 0.0123(3) 0.0154(4) 0.0136(4) -0.0006(3) -0.0003(3) -0.0019(3) C5 0.0114(3) 0.0138(4) 0.0129(3) 0.0004(3) 0.0008(3) -0.0024(3) C6 0.0147(3) 0.0127(4) 0.0134(3) 0.0006(3) 0.0012(3) -0.0021(3) C7 0.0130(3) 0.0132(3) 0.0120(3) -0.0002(3) 0.0001(3) -0.0008(3) C8 0.0167(4) 0.0148(4) 0.0152(4) 0.0006(3) -0.0002(3) 0.0006(3) C9 0.0154(4) 0.0184(4) 0.0172(4) -0.0001(3) -0.0003(3) 0.0033(3) C10 0.0130(4) 0.0201(4) 0.0170(4) -0.0005(3) 0.0005(3) 0.0005(3) C11 0.0117(3) 0.0174(4) 0.0159(4) 0.0010(3) 0.0009(3) -0.0022(3) C12 0.0115(3) 0.0138(4) 0.0121(3) 0.0001(3) 0.0001(3) -0.0017(3) C13 0.0122(3) 0.0129(4) 0.0146(4) 0.0016(3) 0.0004(3) -0.0024(3) C14 0.0116(3) 0.0128(4) 0.0137(4) 0.0006(3) -0.0006(3) -0.0015(3) C15 0.0117(3) 0.0169(4) 0.0160(4) 0.0003(3) -0.0012(3) -0.0008(3) C16 0.0162(4) 0.0169(4) 0.0214(4) 0.0025(3) -0.0020(3) -0.0037(3) O17 0.0159(3) 0.0221(3) 0.0167(3) 0.0034(3) 0.0024(2) -0.0037(3) C18 0.0131(3) 0.0179(4) 0.0141(4) 0.0021(3) -0.0001(3) -0.0014(3) O19 0.0119(3) 0.0255(4) 0.0157(3) 0.0070(3) -0.0026(2) -0.0049(3) C20 0.0175(4) 0.0244(5) 0.0195(4) 0.0044(4) -0.0003(3) 0.0047(4) C21 0.0238(5) 0.0219(5) 0.0248(5) -0.0043(4) -0.0008(4) -0.0023(4) _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 1.3763(12) . ? O1 C2 1.4068(11) . ? C2 O3 1.4388(12) . ? C2 C15 1.5196(14) . ? C2 H2 1.0000 . ? O3 C4 1.3597(12) . ? O4 C4 1.2083(12) . ? C4 C5 1.4781(12) . ? C5 C6 1.3779(13) . ? C5 C14 1.4197(13) . ? C6 C7 1.4178(12) . ? C6 H6 0.9500 . ? C7 C8 1.4226(13) . ? C7 C12 1.4286(13) . ? C8 C9 1.3750(14) . ? C8 H8 0.9500 . ? C9 C10 1.4168(15) . ? C9 H9 0.9500 . ? C10 C11 1.3726(14) . ? C10 H10 0.9500 . ? C11 C12 1.4229(12) . ? C11 H11 0.9500 . ? C12 C13 1.4155(13) . ? C13 C14 1.3700(12) . ? C13 H13 0.9500 . ? C15 O19 1.4268(12) . ? C15 C16 1.5190(14) . ? C15 H15 1.0000 . ? C16 O17 1.4330(13) . ? C16 H161 0.9900 . ? C16 H162 0.9900 . ? O17 C18 1.4260(12) . ? C18 O19 1.4438(12) . ? C18 C21 1.5110(16) . ? C18 C20 1.5180(14) . ? C20 H201 0.9800 . ? C20 H202 0.9800 . ? C20 H203 0.9800 . ? C21 H211 0.9800 . ? C21 H212 0.9800 . ? C21 H213 0.9800 . ? 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 C2 111.76(8) . . ? O1 C2 O3 111.70(7) . . ? O1 C2 C15 108.46(8) . . ? O3 C2 C15 105.58(7) . . ? O1 C2 H2 110.3 . . ? O3 C2 H2 110.3 . . ? C15 C2 H2 110.3 . . ? C4 O3 C2 118.05(7) . . ? O4 C4 O3 118.51(8) . . ? O4 C4 C5 125.71(9) . . ? O3 C4 C5 115.77(8) . . ? C6 C5 C14 120.03(8) . . ? C6 C5 C4 121.42(8) . . ? C14 C5 C4 118.49(8) . . ? C5 C6 C7 120.27(9) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 121.96(9) . . ? C6 C7 C12 119.07(8) . . ? C8 C7 C12 118.97(8) . . ? C9 C8 C7 120.72(9) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.11(9) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.68(9) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.52(9) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 121.32(9) . . ? C13 C12 C7 119.70(8) . . ? C11 C12 C7 118.97(8) . . ? C14 C13 C12 119.73(8) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 O1 119.73(8) . . ? C13 C14 C5 121.19(8) . . ? O1 C14 C5 119.05(8) . . ? O19 C15 C16 103.54(8) . . ? O19 C15 C2 108.16(8) . . ? C16 C15 C2 113.92(8) . . ? O19 C15 H15 110.3 . . ? C16 C15 H15 110.3 . . ? C2 C15 H15 110.3 . . ? O17 C16 C15 102.62(8) . . ? O17 C16 H161 111.2 . . ? C15 C16 H161 111.2 . . ? O17 C16 H162 111.2 . . ? C15 C16 H162 111.2 . . ? H161 C16 H162 109.2 . . ? C18 O17 C16 105.53(7) . . ? O17 C18 O19 105.55(7) . . ? O17 C18 C21 108.67(8) . . ? O19 C18 C21 109.46(9) . . ? O17 C18 C20 111.75(8) . . ? O19 C18 C20 108.49(8) . . ? C21 C18 C20 112.66(9) . . ? C15 O19 C18 109.03(7) . . ? C18 C20 H201 109.5 . . ? C18 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? C18 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? C18 C21 H211 109.5 . . ? C18 C21 H212 109.5 . . ? H211 C21 H212 109.5 . . ? C18 C21 H213 109.5 . . ? H211 C21 H213 109.5 . . ? H212 C21 H213 109.5 . . ? 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 C14 O1 C2 O3 57.88(10) . . . . ? C14 O1 C2 C15 173.83(8) . . . . ? O1 C2 O3 C4 -48.23(12) . . . . ? C15 C2 O3 C4 -165.92(8) . . . . ? C2 O3 C4 O4 -167.60(9) . . . . ? C2 O3 C4 C5 13.05(12) . . . . ? O4 C4 C5 C6 9.22(15) . . . . ? O3 C4 C5 C6 -171.49(8) . . . . ? O4 C4 C5 C14 -168.10(9) . . . . ? O3 C4 C5 C14 11.20(12) . . . . ? C14 C5 C6 C7 -1.31(13) . . . . ? C4 C5 C6 C7 -178.58(9) . . . . ? C5 C6 C7 C8 -178.97(9) . . . . ? C5 C6 C7 C12 0.98(13) . . . . ? C6 C7 C8 C9 178.51(9) . . . . ? C12 C7 C8 C9 -1.44(14) . . . . ? C7 C8 C9 C10 1.08(15) . . . . ? C8 C9 C10 C11 -0.18(15) . . . . ? C9 C10 C11 C12 -0.33(15) . . . . ? C10 C11 C12 C13 -179.01(9) . . . . ? C10 C11 C12 C7 -0.05(14) . . . . ? C6 C7 C12 C13 -0.06(13) . . . . ? C8 C7 C12 C13 179.89(8) . . . . ? C6 C7 C12 C11 -179.04(8) . . . . ? C8 C7 C12 C11 0.91(13) . . . . ? C11 C12 C13 C14 178.44(9) . . . . ? C7 C12 C13 C14 -0.51(13) . . . . ? C12 C13 C14 O1 178.32(8) . . . . ? C12 C13 C14 C5 0.19(13) . . . . ? C2 O1 C14 C13 147.35(9) . . . . ? C2 O1 C14 C5 -34.48(11) . . . . ? C6 C5 C14 C13 0.73(13) . . . . ? C4 C5 C14 C13 178.08(9) . . . . ? C6 C5 C14 O1 -177.41(8) . . . . ? C4 C5 C14 O1 -0.06(13) . . . . ? O1 C2 C15 O19 174.35(7) . . . . ? O3 C2 C15 O19 -65.79(9) . . . . ? O1 C2 C15 C16 59.83(10) . . . . ? O3 C2 C15 C16 179.68(8) . . . . ? O19 C15 C16 O17 -30.29(10) . . . . ? C2 C15 C16 O17 86.95(9) . . . . ? C15 C16 O17 C18 37.55(10) . . . . ? C16 O17 C18 O19 -30.54(10) . . . . ? C16 O17 C18 C21 -147.86(9) . . . . ? C16 O17 C18 C20 87.21(10) . . . . ? C16 C15 O19 C18 12.28(10) . . . . ? C2 C15 O19 C18 -108.92(9) . . . . ? O17 C18 O19 C15 10.50(11) . . . . ? C21 C18 O19 C15 127.29(9) . . . . ? C20 C18 O19 C15 -109.42(9) . . . . ? 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 C6 H6 O1 0.95 2.85 3.3788(12) 116.4 1_545 C10 H10 O3 0.95 2.55 3.4599(12) 159.9 1_655 C10 H10 O19 0.95 2.76 3.3259(13) 118.8 1_655 C11 H11 O19 0.95 2.52 3.2103(12) 129.3 1_655 C2 H2 O17 1.00 2.66 3.5629(12) 149.7 2_545 C15 H15 O4 1.00 2.51 3.3402(13) 139.7 1_565 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 36.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.458 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.058 # Attachment 'ppb.cif' data_ppb _database_code_depnum_ccdc_archive 'CCDC 846988' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 O3' _chemical_formula_sum 'C15 H14 O3' _chemical_formula_weight 242.26 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.438(1) _cell_length_b 7.1267(2) _cell_length_c 16.9373(7) _cell_angle_alpha 90.0 _cell_angle_beta 117.532(6) _cell_angle_gamma 90.0 _cell_volume 2401.70(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7678 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 37.3 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method ? _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98407 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24817 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 37.38 _reflns_number_total 6027 _reflns_number_gt 3786 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0530P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6027 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40175(3) 0.35094(8) 0.34296(4) 0.01767(12) Uani 1 1 d . . . C2 C 0.33726(4) 0.32363(12) 0.26963(5) 0.01636(15) Uani 1 1 d . . . H2 H 0.3277 0.1863 0.2594 0.020 Uiso 1 1 calc R . . O3 O 0.28619(3) 0.41196(9) 0.28581(4) 0.01957(13) Uani 1 1 d . . . O4 O 0.23385(3) 0.38812(10) 0.36869(4) 0.02641(15) Uani 1 1 d . . . C4 C 0.28465(4) 0.35971(12) 0.36246(6) 0.01898(16) Uani 1 1 d . . . C5 C 0.35390(5) 0.23114(13) 0.51686(6) 0.02333(18) Uani 1 1 d . . . H5 H 0.3148 0.2231 0.5250 0.028 Uiso 1 1 calc R . . C6 C 0.41504(5) 0.18935(14) 0.58534(6) 0.02680(19) Uani 1 1 d . . . H6 H 0.4181 0.1514 0.6409 0.032 Uiso 1 1 calc R . . C7 C 0.47483(5) 0.20133(12) 0.57543(6) 0.02238(17) Uani 1 1 d . . . C8 C 0.53953(5) 0.16159(13) 0.64578(6) 0.0295(2) Uani 1 1 d . . . H8 H 0.5440 0.1239 0.7021 0.035 Uiso 1 1 calc R . . C9 C 0.59577(5) 0.17674(13) 0.63385(6) 0.0305(2) Uani 1 1 d . . . H9 H 0.6388 0.1518 0.6822 0.037 Uiso 1 1 calc R . . C10 C 0.59032(4) 0.22876(13) 0.55097(7) 0.02670(19) Uani 1 1 d . . . H10 H 0.6296 0.2379 0.5433 0.032 Uiso 1 1 calc R . . C11 C 0.52850(4) 0.26662(12) 0.48080(6) 0.02122(17) Uani 1 1 d . . . H11 H 0.5250 0.3009 0.4246 0.025 Uiso 1 1 calc R . . C12 C 0.47008(4) 0.25464(11) 0.49222(5) 0.01767(15) Uani 1 1 d . . . C13 C 0.40515(4) 0.29543(11) 0.42169(5) 0.01606(15) Uani 1 1 d . . . C14 C 0.34813(4) 0.28682(11) 0.43300(5) 0.01778(15) Uani 1 1 d . . . C15 C 0.33656(4) 0.41152(12) 0.18801(5) 0.01908(16) Uani 1 1 d . . . H15 H 0.3454 0.5490 0.1990 0.023 Uiso 1 1 calc R . . C16 C 0.39184(5) 0.32592(17) 0.17092(7) 0.0341(2) Uani 1 1 d . . . H161 H 0.4354 0.3441 0.2234 0.051 Uiso 1 1 calc R . . H162 H 0.3922 0.3873 0.1194 0.051 Uiso 1 1 calc R . . H163 H 0.3834 0.1914 0.1590 0.051 Uiso 1 1 calc R . . C17 C 0.26809(5) 0.38540(13) 0.10743(6) 0.02474(18) Uani 1 1 d . . . H171 H 0.2333 0.4412 0.1197 0.037 Uiso 1 1 calc R . . H172 H 0.2590 0.2512 0.0952 0.037 Uiso 1 1 calc R . . H173 H 0.2679 0.4470 0.0556 0.037 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 0.0127(2) 0.0240(3) 0.0152(3) 0.0025(2) 0.0054(2) 0.0004(2) C2 0.0123(3) 0.0196(4) 0.0166(3) 0.0000(3) 0.0061(3) 0.0021(3) O3 0.0148(3) 0.0244(3) 0.0207(3) 0.0030(2) 0.0091(2) 0.0046(2) O4 0.0213(3) 0.0304(4) 0.0336(4) -0.0003(3) 0.0178(3) 0.0026(3) C4 0.0190(4) 0.0185(4) 0.0216(4) -0.0018(3) 0.0112(3) -0.0005(3) C5 0.0289(4) 0.0243(4) 0.0216(4) -0.0025(3) 0.0158(4) -0.0026(3) C6 0.0377(5) 0.0277(5) 0.0162(4) -0.0007(3) 0.0136(4) -0.0016(4) C7 0.0279(4) 0.0183(4) 0.0153(4) -0.0021(3) 0.0052(3) -0.0002(3) C8 0.0363(5) 0.0245(4) 0.0146(4) -0.0017(3) 0.0007(4) 0.0018(4) C9 0.0254(4) 0.0207(4) 0.0247(4) -0.0047(3) -0.0061(3) 0.0031(3) C10 0.0168(4) 0.0205(4) 0.0316(5) -0.0030(4) 0.0017(3) 0.0009(3) C11 0.0167(4) 0.0191(4) 0.0226(4) -0.0005(3) 0.0045(3) 0.0003(3) C12 0.0178(4) 0.0146(3) 0.0157(3) -0.0017(3) 0.0036(3) -0.0002(3) C13 0.0172(3) 0.0153(3) 0.0150(3) -0.0006(3) 0.0069(3) -0.0003(3) C14 0.0187(4) 0.0182(4) 0.0175(4) -0.0017(3) 0.0093(3) -0.0011(3) C15 0.0174(3) 0.0223(4) 0.0174(4) 0.0027(3) 0.0079(3) 0.0027(3) C16 0.0312(5) 0.0502(7) 0.0278(5) 0.0120(5) 0.0194(4) 0.0161(5) C17 0.0245(4) 0.0263(4) 0.0175(4) 0.0013(3) 0.0046(3) 0.0001(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 C13 1.3588(9) . ? O1 C2 1.4188(9) . ? C2 O3 1.4404(9) . ? C2 C15 1.5112(11) . ? C2 H2 1.0000 . ? O3 C4 1.3662(10) . ? O4 C4 1.2094(9) . ? C4 C14 1.4674(12) . ? C5 C6 1.3583(13) . ? C5 C14 1.4220(12) . ? C5 H5 0.9500 . ? C6 C7 1.4295(13) . ? C6 H6 0.9500 . ? C7 C12 1.4152(12) . ? C7 C8 1.4171(13) . ? C8 C9 1.3714(15) . ? C8 H8 0.9500 . ? C9 C10 1.4014(14) . ? C9 H9 0.9500 . ? C10 C11 1.3730(12) . ? C10 H10 0.9500 . ? C11 C12 1.4134(12) . ? C11 H11 0.9500 . ? C12 C13 1.4231(11) . ? C13 C14 1.3797(11) . ? C15 C17 1.5229(12) . ? C15 C16 1.5252(12) . ? C15 H15 1.0000 . ? C16 H161 0.9800 . ? C16 H162 0.9800 . ? C16 H163 0.9800 . ? C17 H171 0.9800 . ? C17 H172 0.9800 . ? C17 H173 0.9800 . ? 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 C13 O1 C2 113.01(6) . . ? O1 C2 O3 110.65(6) . . ? O1 C2 C15 108.61(6) . . ? O3 C2 C15 108.67(6) . . ? O1 C2 H2 109.6 . . ? O3 C2 H2 109.6 . . ? C15 C2 H2 109.6 . . ? C4 O3 C2 115.69(6) . . ? O4 C4 O3 118.44(8) . . ? O4 C4 C14 125.99(8) . . ? O3 C4 C14 115.38(7) . . ? C6 C5 C14 120.25(8) . . ? C6 C5 H5 119.9 . . ? C14 C5 H5 119.9 . . ? C5 C6 C7 121.26(8) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C12 C7 C8 117.86(8) . . ? C12 C7 C6 119.36(8) . . ? C8 C7 C6 122.78(8) . . ? C9 C8 C7 121.00(9) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 120.54(8) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 120.30(9) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.96(9) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 120.32(7) . . ? C11 C12 C13 121.82(7) . . ? C7 C12 C13 117.86(7) . . ? O1 C13 C14 120.94(7) . . ? O1 C13 C12 117.03(7) . . ? C14 C13 C12 121.97(7) . . ? C13 C14 C5 119.28(8) . . ? C13 C14 C4 118.99(7) . . ? C5 C14 C4 121.19(7) . . ? C2 C15 C17 110.41(7) . . ? C2 C15 C16 110.02(7) . . ? C17 C15 C16 110.67(8) . . ? C2 C15 H15 108.6 . . ? C17 C15 H15 108.6 . . ? C16 C15 H15 108.6 . . ? C15 C16 H161 109.5 . . ? C15 C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? C15 C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? C15 C17 H171 109.5 . . ? C15 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C15 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? 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 C13 O1 C2 O3 53.81(9) . . . . ? C13 O1 C2 C15 173.00(7) . . . . ? O1 C2 O3 C4 -55.00(9) . . . . ? C15 C2 O3 C4 -174.16(7) . . . . ? C2 O3 C4 O4 -160.75(7) . . . . ? C2 O3 C4 C14 23.98(10) . . . . ? C14 C5 C6 C7 0.46(14) . . . . ? C5 C6 C7 C12 -1.10(13) . . . . ? C5 C6 C7 C8 179.01(9) . . . . ? C12 C7 C8 C9 0.83(13) . . . . ? C6 C7 C8 C9 -179.27(9) . . . . ? C7 C8 C9 C10 -1.18(14) . . . . ? C8 C9 C10 C11 0.50(14) . . . . ? C9 C10 C11 C12 0.50(13) . . . . ? C10 C11 C12 C7 -0.83(13) . . . . ? C10 C11 C12 C13 179.04(8) . . . . ? C8 C7 C12 C11 0.17(12) . . . . ? C6 C7 C12 C11 -179.73(8) . . . . ? C8 C7 C12 C13 -179.70(8) . . . . ? C6 C7 C12 C13 0.40(12) . . . . ? C2 O1 C13 C14 -23.94(10) . . . . ? C2 O1 C13 C12 158.59(7) . . . . ? C11 C12 C13 O1 -1.49(12) . . . . ? C7 C12 C13 O1 178.38(7) . . . . ? C11 C12 C13 C14 -178.93(8) . . . . ? C7 C12 C13 C14 0.94(12) . . . . ? O1 C13 C14 C5 -178.93(7) . . . . ? C12 C13 C14 C5 -1.58(12) . . . . ? O1 C13 C14 C4 -7.20(12) . . . . ? C12 C13 C14 C4 170.14(7) . . . . ? C6 C5 C14 C13 0.87(13) . . . . ? C6 C5 C14 C4 -170.67(8) . . . . ? O4 C4 C14 C13 -167.76(8) . . . . ? O3 C4 C14 C13 7.09(11) . . . . ? O4 C4 C14 C5 3.80(14) . . . . ? O3 C4 C14 C5 178.65(7) . . . . ? O1 C2 C15 C17 179.98(7) . . . . ? O3 C2 C15 C17 -59.59(9) . . . . ? O1 C2 C15 C16 57.53(10) . . . . ? O3 C2 C15 C16 177.96(7) . . . . ? 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 C5 H5 O4 0.95 2.62 3.4473(11) 145.4 7_556 C17 H172 O4 0.98 2.65 3.5695(11) 157.1 4_545 _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.511 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.056 # Attachment 'ppb354.cif' data_ppb354 _database_code_depnum_ccdc_archive 'CCDC 846989' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 O3' _chemical_formula_sum 'C16 H16 O3' _chemical_formula_weight 256.29 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.8830(2) _cell_length_b 14.6412(3) _cell_length_c 15.4699(3) _cell_angle_alpha 90.0 _cell_angle_beta 108.565(2) _cell_angle_gamma 90.0 _cell_volume 2551.42(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8390 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 37.22 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method ? _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99467 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26764 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 37.33 _reflns_number_total 6411 _reflns_number_gt 3924 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0500P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6411 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.45783(5) 0.14266(4) 0.35091(4) 0.01857(12) Uani 1 1 d . . . C2 C 0.57228(7) 0.10618(5) 0.39498(5) 0.01617(15) Uani 1 1 d . . . H2 H 0.6284 0.1258 0.3622 0.019 Uiso 1 1 calc R . . O3 O 0.61553(5) 0.13624(4) 0.48866(4) 0.01829(12) Uani 1 1 d . . . O4 O 0.67777(5) 0.25844(4) 0.57527(4) 0.02149(14) Uani 1 1 d . . . C4 C 0.61893(7) 0.22824(5) 0.50217(5) 0.01620(15) Uani 1 1 d . . . C5 C 0.54145(7) 0.28237(5) 0.42602(5) 0.01519(14) Uani 1 1 d . . . C6 C 0.54335(7) 0.37621(5) 0.42887(5) 0.01657(15) Uani 1 1 d . . . H6 H 0.6010 0.4066 0.4774 0.020 Uiso 1 1 calc R . . C7 C 0.46075(7) 0.42798(6) 0.36060(5) 0.01683(15) Uani 1 1 d . . . C8 C 0.46109(7) 0.52477(6) 0.36154(6) 0.02017(16) Uani 1 1 d . . . H8 H 0.5192 0.5564 0.4086 0.024 Uiso 1 1 calc R . . C9 C 0.37848(8) 0.57315(6) 0.29529(6) 0.02341(18) Uani 1 1 d . . . H9 H 0.3791 0.6380 0.2969 0.028 Uiso 1 1 calc R . . C10 C 0.29243(8) 0.52659(6) 0.22463(6) 0.02390(18) Uani 1 1 d . . . H10 H 0.2356 0.5607 0.1788 0.029 Uiso 1 1 calc R . . C11 C 0.28944(7) 0.43343(6) 0.22104(6) 0.02142(17) Uani 1 1 d . . . H11 H 0.2310 0.4034 0.1728 0.026 Uiso 1 1 calc R . . C12 C 0.37337(7) 0.38094(6) 0.28914(5) 0.01701(15) Uani 1 1 d . . . C13 C 0.37327(7) 0.28417(6) 0.28673(5) 0.01776(15) Uani 1 1 d . . . H13 H 0.3156 0.2524 0.2394 0.021 Uiso 1 1 calc R . . C14 C 0.45671(7) 0.23689(5) 0.35291(5) 0.01580(15) Uani 1 1 d . . . C15 C 0.56398(7) 0.00381(5) 0.39491(6) 0.01803(15) Uani 1 1 d . . . H151 H 0.5275 -0.0178 0.3315 0.022 Uiso 1 1 calc R . . H152 H 0.5115 -0.0148 0.4303 0.022 Uiso 1 1 calc R . . C16 C 0.68502(7) -0.04177(6) 0.43571(6) 0.02002(16) Uani 1 1 d . . . H161 H 0.7329 -0.0307 0.3948 0.024 Uiso 1 1 calc R . . H162 H 0.7267 -0.0126 0.4950 0.024 Uiso 1 1 calc R . . C17 C 0.67865(8) -0.14447(6) 0.45036(6) 0.02433(18) Uani 1 1 d . . . H171 H 0.7604 -0.1693 0.4710 0.029 Uiso 1 1 calc R . . H172 H 0.6438 -0.1550 0.4997 0.029 Uiso 1 1 calc R . . C18 C 0.60609(9) -0.19697(6) 0.36608(7) 0.0291(2) Uani 1 1 d . . . H181 H 0.6062 -0.2621 0.3808 0.044 Uiso 1 1 calc R . . H182 H 0.6411 -0.1885 0.3172 0.044 Uiso 1 1 calc R . . H183 H 0.5243 -0.1741 0.3460 0.044 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 0.0140(3) 0.0180(3) 0.0198(3) -0.0038(2) -0.0001(2) 0.0002(2) C2 0.0137(3) 0.0198(4) 0.0129(3) -0.0013(3) 0.0012(3) 0.0003(3) O3 0.0207(3) 0.0175(3) 0.0139(3) -0.0011(2) 0.0016(2) -0.0010(2) O4 0.0212(3) 0.0236(3) 0.0146(3) -0.0022(2) -0.0015(2) 0.0000(2) C4 0.0144(3) 0.0180(4) 0.0153(3) -0.0005(3) 0.0035(3) -0.0009(3) C5 0.0128(3) 0.0190(4) 0.0125(3) -0.0008(3) 0.0022(3) 0.0000(3) C6 0.0141(3) 0.0195(4) 0.0146(3) -0.0018(3) 0.0025(3) -0.0010(3) C7 0.0152(3) 0.0200(4) 0.0155(4) -0.0003(3) 0.0052(3) 0.0019(3) C8 0.0201(4) 0.0202(4) 0.0206(4) -0.0006(3) 0.0071(3) 0.0005(3) C9 0.0258(4) 0.0207(4) 0.0258(4) 0.0032(3) 0.0111(4) 0.0062(3) C10 0.0219(4) 0.0284(5) 0.0205(4) 0.0048(3) 0.0054(3) 0.0111(3) C11 0.0169(4) 0.0287(5) 0.0164(4) -0.0005(3) 0.0021(3) 0.0070(3) C12 0.0141(3) 0.0225(4) 0.0141(3) -0.0008(3) 0.0041(3) 0.0040(3) C13 0.0136(3) 0.0228(4) 0.0148(4) -0.0046(3) 0.0014(3) 0.0018(3) C14 0.0135(3) 0.0181(4) 0.0149(3) -0.0032(3) 0.0033(3) 0.0003(3) C15 0.0179(4) 0.0188(4) 0.0165(4) -0.0019(3) 0.0042(3) -0.0019(3) C16 0.0184(4) 0.0178(4) 0.0225(4) -0.0003(3) 0.0047(3) -0.0008(3) C17 0.0259(4) 0.0187(4) 0.0251(4) 0.0015(3) 0.0035(3) 0.0003(3) C18 0.0296(5) 0.0212(4) 0.0330(5) -0.0054(4) 0.0050(4) -0.0014(4) _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 1.3801(10) . ? O1 C2 1.4175(9) . ? C2 O3 1.4435(9) . ? C2 C15 1.5021(11) . ? C2 H2 1.0000 . ? O3 C4 1.3618(9) . ? O4 C4 1.2082(9) . ? C4 C5 1.4741(11) . ? C5 C6 1.3746(11) . ? C5 C14 1.4182(10) . ? C6 C7 1.4118(11) . ? C6 H6 0.9500 . ? C7 C8 1.4172(12) . ? C7 C12 1.4296(11) . ? C8 C9 1.3693(12) . ? C8 H8 0.9500 . ? C9 C10 1.4119(13) . ? C9 H9 0.9500 . ? C10 C11 1.3652(13) . ? C10 H10 0.9500 . ? C11 C12 1.4235(11) . ? C11 H11 0.9500 . ? C12 C13 1.4173(11) . ? C13 C14 1.3653(11) . ? C13 H13 0.9500 . ? C15 C16 1.5279(12) . ? C15 H151 0.9900 . ? C15 H152 0.9900 . ? C16 C17 1.5261(12) . ? C16 H161 0.9900 . ? C16 H162 0.9900 . ? C17 C18 1.5226(12) . ? C17 H171 0.9900 . ? C17 H172 0.9900 . ? C18 H181 0.9800 . ? C18 H182 0.9800 . ? C18 H183 0.9800 . ? 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 C2 112.36(6) . . ? O1 C2 O3 110.38(6) . . ? O1 C2 C15 108.84(6) . . ? O3 C2 C15 107.89(6) . . ? O1 C2 H2 109.9 . . ? O3 C2 H2 109.9 . . ? C15 C2 H2 109.9 . . ? C4 O3 C2 116.06(6) . . ? O4 C4 O3 119.06(7) . . ? O4 C4 C5 125.40(8) . . ? O3 C4 C5 115.39(6) . . ? C6 C5 C14 119.68(7) . . ? C6 C5 C4 120.81(7) . . ? C14 C5 C4 119.28(7) . . ? C5 C6 C7 120.82(7) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C8 122.02(7) . . ? C6 C7 C12 118.72(7) . . ? C8 C7 C12 119.25(7) . . ? C9 C8 C7 120.70(8) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 119.98(8) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 121.13(8) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.42(8) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 121.72(7) . . ? C13 C12 C7 119.75(7) . . ? C11 C12 C7 118.52(7) . . ? C14 C13 C12 119.53(7) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 O1 119.99(7) . . ? C13 C14 C5 121.44(7) . . ? O1 C14 C5 118.54(7) . . ? C2 C15 C16 112.49(7) . . ? C2 C15 H151 109.1 . . ? C16 C15 H151 109.1 . . ? C2 C15 H152 109.1 . . ? C16 C15 H152 109.1 . . ? H151 C15 H152 107.8 . . ? C17 C16 C15 114.01(7) . . ? C17 C16 H161 108.7 . . ? C15 C16 H161 108.7 . . ? C17 C16 H162 108.7 . . ? C15 C16 H162 108.7 . . ? H161 C16 H162 107.6 . . ? C18 C17 C16 114.30(8) . . ? C18 C17 H171 108.7 . . ? C16 C17 H171 108.7 . . ? C18 C17 H172 108.7 . . ? C16 C17 H172 108.7 . . ? H171 C17 H172 107.6 . . ? C17 C18 H181 109.5 . . ? C17 C18 H182 109.5 . . ? H181 C18 H182 109.5 . . ? C17 C18 H183 109.5 . . ? H181 C18 H183 109.5 . . ? H182 C18 H183 109.5 . . ? 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 C14 O1 C2 O3 58.20(8) . . . . ? C14 O1 C2 C15 176.43(6) . . . . ? O1 C2 O3 C4 -55.67(8) . . . . ? C15 C2 O3 C4 -174.48(6) . . . . ? C2 O3 C4 O4 -163.48(7) . . . . ? C2 O3 C4 C5 20.76(9) . . . . ? O4 C4 C5 C6 9.18(13) . . . . ? O3 C4 C5 C6 -175.37(7) . . . . ? O4 C4 C5 C14 -165.18(8) . . . . ? O3 C4 C5 C14 10.28(10) . . . . ? C14 C5 C6 C7 0.98(12) . . . . ? C4 C5 C6 C7 -173.35(7) . . . . ? C5 C6 C7 C8 -179.63(7) . . . . ? C5 C6 C7 C12 1.16(12) . . . . ? C6 C7 C8 C9 -178.80(8) . . . . ? C12 C7 C8 C9 0.40(12) . . . . ? C7 C8 C9 C10 -0.57(13) . . . . ? C8 C9 C10 C11 0.26(13) . . . . ? C9 C10 C11 C12 0.22(13) . . . . ? C10 C11 C12 C13 -179.34(8) . . . . ? C10 C11 C12 C7 -0.37(12) . . . . ? C6 C7 C12 C13 -1.71(11) . . . . ? C8 C7 C12 C13 179.06(7) . . . . ? C6 C7 C12 C11 179.30(7) . . . . ? C8 C7 C12 C11 0.07(11) . . . . ? C11 C12 C13 C14 179.04(8) . . . . ? C7 C12 C13 C14 0.08(12) . . . . ? C12 C13 C14 O1 -179.63(7) . . . . ? C12 C13 C14 C5 2.12(12) . . . . ? C2 O1 C14 C13 153.69(7) . . . . ? C2 O1 C14 C5 -28.01(9) . . . . ? C6 C5 C14 C13 -2.69(12) . . . . ? C4 C5 C14 C13 171.73(7) . . . . ? C6 C5 C14 O1 179.03(7) . . . . ? C4 C5 C14 O1 -6.55(11) . . . . ? O1 C2 C15 C16 176.28(7) . . . . ? O3 C2 C15 C16 -63.93(8) . . . . ? C2 C15 C16 C17 171.08(7) . . . . ? C15 C16 C17 C18 52.85(11) . . . . ? 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 C2 H2 O4 1.00 2.77 3.4774(10) 127.7 7_656 C9 H9 O4 0.95 2.74 3.3747(11) 124.7 5_666 C10 H10 O1 0.95 2.50 3.2991(10) 141.4 4 C11 H11 O4 0.95 2.77 3.5822(11) 143.7 8_455 C11 H11 O3 0.95 2.80 3.6747(10) 153.4 8_455 C13 H13 O4 0.95 2.55 3.4130(10) 151.0 8_455 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.570 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.060 # Attachment 'ppb356.cif' data_ppb356 _database_code_depnum_ccdc_archive 'CCDC 846990' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 O3' _chemical_formula_sum 'C14 H12 O3' _chemical_formula_weight 228.24 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 9.0829(2) _cell_length_b 8.4907(2) _cell_length_c 14.0688(3) _cell_angle_alpha 90.0 _cell_angle_beta 96.172(2) _cell_angle_gamma 90.0 _cell_volume 1078.70(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9704 _cell_measurement_theta_min 3.28 _cell_measurement_theta_max 40.8 _exptl_crystal_description colorless _exptl_crystal_colour prism _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method ? _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99712 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29349 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 40.96 _reflns_number_total 6938 _reflns_number_gt 4419 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0870P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6938 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1552 _refine_ls_wR_factor_gt 0.1472 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.49114(6) 0.53363(8) 0.72185(4) 0.01577(12) Uani 1 1 d . . . C2 C 0.37445(9) 0.51106(10) 0.77947(6) 0.01456(14) Uani 1 1 d . . . H2 H 0.3215 0.6131 0.7860 0.017 Uiso 1 1 calc R . . O3 O 0.27134(6) 0.39504(7) 0.73628(4) 0.01500(11) Uani 1 1 d . . . O4 O 0.10172(7) 0.35903(8) 0.61293(5) 0.02181(14) Uani 1 1 d . . . C4 C 0.21144(9) 0.42894(10) 0.64586(6) 0.01505(14) Uani 1 1 d . . . C5 C 0.29291(8) 0.54545(10) 0.59443(6) 0.01426(13) Uani 1 1 d . . . C6 C 0.23428(9) 0.60441(10) 0.50711(6) 0.01553(14) Uani 1 1 d . . . H6 H 0.1368 0.5758 0.4816 0.019 Uiso 1 1 calc R . . C7 C 0.31869(9) 0.70720(10) 0.45542(6) 0.01543(14) Uani 1 1 d . . . C8 C 0.25878(10) 0.77732(11) 0.36799(6) 0.01841(15) Uani 1 1 d . . . H8 H 0.1609 0.7521 0.3418 0.022 Uiso 1 1 calc R . . C9 C 0.34161(10) 0.88121(11) 0.32126(6) 0.01909(16) Uani 1 1 d . . . H9 H 0.2992 0.9310 0.2643 0.023 Uiso 1 1 calc R . . C10 C 0.48916(10) 0.91454(11) 0.35722(7) 0.02014(16) Uani 1 1 d . . . H10 H 0.5460 0.9848 0.3234 0.024 Uiso 1 1 calc R . . C11 C 0.55181(9) 0.84673(11) 0.44057(6) 0.01810(15) Uani 1 1 d . . . H11 H 0.6518 0.8695 0.4635 0.022 Uiso 1 1 calc R . . C12 C 0.46805(9) 0.74286(10) 0.49271(6) 0.01549(14) Uani 1 1 d . . . C13 C 0.52493(9) 0.68170(11) 0.58283(6) 0.01720(15) Uani 1 1 d . . . H13 H 0.6234 0.7056 0.6085 0.021 Uiso 1 1 calc R . . C14 C 0.43829(9) 0.58831(9) 0.63296(6) 0.01450(13) Uani 1 1 d . . . C15 C 0.43495(10) 0.45268(11) 0.87702(6) 0.01758(15) Uani 1 1 d . . . H151 H 0.3509 0.4263 0.9135 0.021 Uiso 1 1 calc R . . H152 H 0.4915 0.5389 0.9114 0.021 Uiso 1 1 calc R . . C16 C 0.53499(10) 0.30905(12) 0.87553(7) 0.02081(17) Uani 1 1 d . . . H161 H 0.5698 0.2782 0.9413 0.031 Uiso 1 1 calc R . . H162 H 0.6202 0.3346 0.8411 0.031 Uiso 1 1 calc R . . H163 H 0.4794 0.2218 0.8432 0.031 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 0.0141(2) 0.0207(3) 0.0120(2) 0.0019(2) -0.00124(18) -0.0003(2) C2 0.0157(3) 0.0144(3) 0.0133(3) -0.0024(2) 0.0004(2) -0.0002(3) O3 0.0170(2) 0.0143(2) 0.0131(2) 0.00020(19) -0.00133(19) -0.0016(2) O4 0.0206(3) 0.0216(3) 0.0215(3) 0.0039(2) -0.0052(2) -0.0087(2) C4 0.0164(3) 0.0134(3) 0.0147(3) 0.0010(2) -0.0015(2) -0.0012(3) C5 0.0142(3) 0.0146(3) 0.0137(3) 0.0007(2) -0.0002(2) -0.0020(2) C6 0.0140(3) 0.0168(3) 0.0155(3) 0.0004(3) -0.0001(2) -0.0002(3) C7 0.0163(3) 0.0159(3) 0.0139(3) 0.0007(2) 0.0011(2) 0.0005(3) C8 0.0201(3) 0.0206(4) 0.0142(3) 0.0022(3) 0.0002(3) 0.0004(3) C9 0.0230(4) 0.0196(4) 0.0152(3) 0.0035(3) 0.0045(3) 0.0037(3) C10 0.0225(4) 0.0203(4) 0.0190(4) 0.0039(3) 0.0084(3) 0.0004(3) C11 0.0174(3) 0.0197(4) 0.0180(4) 0.0015(3) 0.0055(3) -0.0006(3) C12 0.0172(3) 0.0147(3) 0.0145(3) 0.0000(2) 0.0014(2) -0.0008(3) C13 0.0148(3) 0.0196(4) 0.0168(3) 0.0010(3) -0.0004(3) -0.0028(3) C14 0.0152(3) 0.0145(3) 0.0131(3) 0.0006(2) -0.0017(2) -0.0012(3) C15 0.0213(4) 0.0197(4) 0.0115(3) -0.0014(3) 0.0003(3) 0.0002(3) C16 0.0213(4) 0.0244(4) 0.0165(4) 0.0032(3) 0.0006(3) 0.0043(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 C14 1.3714(10) . ? O1 C2 1.4149(10) . ? C2 O3 1.4472(10) . ? C2 C15 1.5064(11) . ? C2 H2 1.0000 . ? O3 C4 1.3596(10) . ? O4 C4 1.2086(10) . ? C4 C5 1.4713(11) . ? C5 C6 1.3794(11) . ? C5 C14 1.4199(11) . ? C6 C7 1.4136(12) . ? C6 H6 0.9500 . ? C7 C8 1.4212(12) . ? C7 C12 1.4333(11) . ? C8 C9 1.3721(13) . ? C8 H8 0.9500 . ? C9 C10 1.4094(13) . ? C9 H9 0.9500 . ? C10 C11 1.3737(13) . ? C10 H10 0.9500 . ? C11 C12 1.4193(12) . ? C11 H11 0.9500 . ? C12 C13 1.4154(12) . ? C13 C14 1.3655(12) . ? C13 H13 0.9500 . ? C15 C16 1.5223(13) . ? C15 H151 0.9900 . ? C15 H152 0.9900 . ? C16 H161 0.9800 . ? C16 H162 0.9800 . ? C16 H163 0.9800 . ? 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 C2 110.98(6) . . ? O1 C2 O3 110.03(6) . . ? O1 C2 C15 110.14(6) . . ? O3 C2 C15 108.34(7) . . ? O1 C2 H2 109.4 . . ? O3 C2 H2 109.4 . . ? C15 C2 H2 109.4 . . ? C4 O3 C2 115.12(6) . . ? O4 C4 O3 119.02(7) . . ? O4 C4 C5 125.40(8) . . ? O3 C4 C5 115.51(7) . . ? C6 C5 C14 120.07(7) . . ? C6 C5 C4 121.03(7) . . ? C14 C5 C4 118.74(7) . . ? C5 C6 C7 120.23(7) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 121.70(7) . . ? C6 C7 C12 119.11(7) . . ? C8 C7 C12 119.18(8) . . ? C9 C8 C7 120.35(8) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.42(8) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.85(8) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.38(8) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 121.78(8) . . ? C13 C12 C7 119.36(7) . . ? C11 C12 C7 118.75(8) . . ? C14 C13 C12 120.04(7) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 O1 120.19(7) . . ? C13 C14 C5 121.03(7) . . ? O1 C14 C5 118.77(7) . . ? C2 C15 C16 114.26(7) . . ? C2 C15 H151 108.7 . . ? C16 C15 H151 108.7 . . ? C2 C15 H152 108.7 . . ? C16 C15 H152 108.7 . . ? H151 C15 H152 107.6 . . ? C15 C16 H161 109.5 . . ? C15 C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? C15 C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? 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 C14 O1 C2 O3 61.23(8) . . . . ? C14 O1 C2 C15 -179.40(7) . . . . ? O1 C2 O3 C4 -57.17(9) . . . . ? C15 C2 O3 C4 -177.63(7) . . . . ? C2 O3 C4 O4 -163.46(8) . . . . ? C2 O3 C4 C5 19.34(10) . . . . ? O4 C4 C5 C6 11.17(14) . . . . ? O3 C4 C5 C6 -171.84(7) . . . . ? O4 C4 C5 C14 -164.38(9) . . . . ? O3 C4 C5 C14 12.62(11) . . . . ? C14 C5 C6 C7 0.23(13) . . . . ? C4 C5 C6 C7 -175.25(8) . . . . ? C5 C6 C7 C8 -176.28(8) . . . . ? C5 C6 C7 C12 3.06(12) . . . . ? C6 C7 C8 C9 177.56(8) . . . . ? C12 C7 C8 C9 -1.78(13) . . . . ? C7 C8 C9 C10 2.71(14) . . . . ? C8 C9 C10 C11 -1.46(14) . . . . ? C9 C10 C11 C12 -0.73(14) . . . . ? C10 C11 C12 C13 -174.49(8) . . . . ? C10 C11 C12 C7 1.61(13) . . . . ? C6 C7 C12 C13 -3.54(12) . . . . ? C8 C7 C12 C13 175.82(8) . . . . ? C6 C7 C12 C11 -179.73(8) . . . . ? C8 C7 C12 C11 -0.37(12) . . . . ? C11 C12 C13 C14 176.76(8) . . . . ? C7 C12 C13 C14 0.69(13) . . . . ? C12 C13 C14 O1 -177.58(8) . . . . ? C12 C13 C14 C5 2.67(13) . . . . ? C2 O1 C14 C13 150.63(8) . . . . ? C2 O1 C14 C5 -29.63(10) . . . . ? C6 C5 C14 C13 -3.19(13) . . . . ? C4 C5 C14 C13 172.40(8) . . . . ? C6 C5 C14 O1 177.07(7) . . . . ? C4 C5 C14 O1 -7.35(12) . . . . ? O1 C2 C15 C16 -52.10(10) . . . . ? O3 C2 C15 C16 68.29(9) . . . . ? 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 C2 H2 O3 1.00 2.55 3.5170(10) 163.6 2_556 C2 H2 O4 1.00 2.58 3.3162(11) 130.4 2_556 C6 H6 O4 0.95 2.48 3.3398(10) 150.5 3_566 C8 H8 O4 0.95 2.70 3.5104(11) 143.1 3_566 C8 H8 O1 0.95 2.82 3.4116(10) 121.0 4_575 C9 H9 O1 0.95 2.81 3.4140(11) 122.0 4_575 C10 H10 O3 0.95 2.70 3.6076(11) 161.0 4_675 C15 H152 O4 0.99 2.86 3.4706(12) 120.9 2_556 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 40.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.862 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.087 # Attachment 'ppb357.cif' data_ppb357 _database_code_depnum_ccdc_archive 'CCDC 846991' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 O3' _chemical_formula_sum 'C12 H8 O3' _chemical_formula_weight 200.18 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.0779(8) _cell_length_b 6.2280(3) _cell_length_c 7.2121(3) _cell_angle_alpha 90.0 _cell_angle_beta 100.161(4) _cell_angle_gamma 90.0 _cell_volume 887.69(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3322 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 37.18 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method ? _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92108 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9430 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 37.26 _reflns_number_total 4379 _reflns_number_gt 2657 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0540P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4379 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.13028(4) 0.30178(12) 0.15437(10) 0.01615(16) Uani 1 1 d . . . C2 C 0.06920(5) 0.18576(18) 0.09445(15) 0.0161(2) Uani 1 1 d . . . H21 H 0.0727 0.1042 -0.0213 0.019 Uiso 1 1 calc R . . H22 H 0.0312 0.2882 0.0636 0.019 Uiso 1 1 calc R . . O3 O 0.05537(4) 0.03966(13) 0.23708(10) 0.01664(16) Uani 1 1 d . . . O4 O 0.09342(4) -0.24933(13) 0.40083(11) 0.01980(17) Uani 1 1 d . . . C4 C 0.10573(5) -0.09938(17) 0.30757(14) 0.01398(19) Uani 1 1 d . . . C5 C 0.17431(5) -0.03917(16) 0.27563(13) 0.01243(18) Uani 1 1 d . . . C6 C 0.22856(5) -0.17314(17) 0.33271(14) 0.01352(19) Uani 1 1 d . . . H6 H 0.2213 -0.3117 0.3805 0.016 Uiso 1 1 calc R . . C7 C 0.29519(5) -0.10587(17) 0.32076(13) 0.01354(19) Uani 1 1 d . . . C8 C 0.35232(5) -0.23921(19) 0.38245(14) 0.0171(2) Uani 1 1 d . . . H8 H 0.3461 -0.3782 0.4310 0.021 Uiso 1 1 calc R . . C9 C 0.41635(6) -0.1686(2) 0.37236(15) 0.0205(2) Uani 1 1 d . . . H9 H 0.4542 -0.2587 0.4145 0.025 Uiso 1 1 calc R . . C10 C 0.42634(6) 0.0370(2) 0.29979(15) 0.0212(2) Uani 1 1 d . . . H10 H 0.4709 0.0838 0.2928 0.025 Uiso 1 1 calc R . . C11 C 0.37223(5) 0.17029(19) 0.23908(14) 0.0180(2) Uani 1 1 d . . . H11 H 0.3797 0.3079 0.1898 0.022 Uiso 1 1 calc R . . C12 C 0.30509(5) 0.10378(17) 0.24950(13) 0.01400(19) Uani 1 1 d . . . C13 C 0.24846(5) 0.23893(18) 0.19066(13) 0.01428(19) Uani 1 1 d . . . H13 H 0.2546 0.3782 0.1427 0.017 Uiso 1 1 calc R . . C14 C 0.18476(5) 0.16769(16) 0.20331(13) 0.01266(18) Uani 1 1 d . . . 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 0.0140(3) 0.0131(4) 0.0212(4) 0.0009(3) 0.0027(3) 0.0014(3) C2 0.0124(4) 0.0174(5) 0.0182(5) 0.0030(4) 0.0018(3) 0.0005(4) O3 0.0120(3) 0.0190(4) 0.0193(3) 0.0033(3) 0.0041(3) 0.0015(3) O4 0.0164(4) 0.0198(4) 0.0236(4) 0.0053(3) 0.0045(3) -0.0033(3) C4 0.0117(4) 0.0154(5) 0.0147(4) -0.0011(4) 0.0023(3) -0.0005(4) C5 0.0115(4) 0.0134(5) 0.0126(4) -0.0007(4) 0.0026(3) -0.0010(3) C6 0.0145(4) 0.0131(5) 0.0132(4) 0.0008(4) 0.0032(3) -0.0004(4) C7 0.0121(4) 0.0167(5) 0.0119(4) -0.0008(4) 0.0024(3) 0.0003(4) C8 0.0149(5) 0.0219(5) 0.0144(4) 0.0005(4) 0.0020(3) 0.0037(4) C9 0.0135(5) 0.0308(6) 0.0168(5) -0.0016(4) 0.0018(4) 0.0049(4) C10 0.0128(5) 0.0340(7) 0.0171(5) -0.0032(5) 0.0038(4) -0.0033(4) C11 0.0153(5) 0.0232(6) 0.0161(4) -0.0019(4) 0.0042(4) -0.0054(4) C12 0.0129(4) 0.0175(5) 0.0120(4) -0.0018(4) 0.0031(3) -0.0018(4) C13 0.0151(5) 0.0133(5) 0.0145(4) 0.0009(4) 0.0030(3) -0.0020(4) C14 0.0129(4) 0.0122(5) 0.0128(4) -0.0005(3) 0.0023(3) 0.0009(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 C14 1.3720(12) . ? O1 C2 1.4234(13) . ? C2 O3 1.4366(13) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? O3 C4 1.3599(12) . ? O4 C4 1.2017(13) . ? C4 C5 1.4837(14) . ? C5 C6 1.3762(14) . ? C5 C14 1.4194(14) . ? C6 C7 1.4189(14) . ? C6 H6 0.9500 . ? C7 C8 1.4224(14) . ? C7 C12 1.4299(15) . ? C8 C9 1.3728(15) . ? C8 H8 0.9500 . ? C9 C10 1.4107(18) . ? C9 H9 0.9500 . ? C10 C11 1.3761(16) . ? C10 H10 0.9500 . ? C11 C12 1.4248(14) . ? C11 H11 0.9500 . ? C12 C13 1.4182(15) . ? C13 C14 1.3718(14) . ? C13 H13 0.9500 . ? 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 C2 111.98(8) . . ? O1 C2 O3 111.66(8) . . ? O1 C2 H21 109.3 . . ? O3 C2 H21 109.3 . . ? O1 C2 H22 109.3 . . ? O3 C2 H22 109.3 . . ? H21 C2 H22 107.9 . . ? C4 O3 C2 116.50(8) . . ? O4 C4 O3 119.43(9) . . ? O4 C4 C5 124.85(9) . . ? O3 C4 C5 115.48(9) . . ? C6 C5 C14 119.98(9) . . ? C6 C5 C4 120.50(9) . . ? C14 C5 C4 119.20(9) . . ? C5 C6 C7 120.52(10) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 121.71(10) . . ? C6 C7 C12 118.93(9) . . ? C8 C7 C12 119.34(9) . . ? C9 C8 C7 120.49(11) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.42(10) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.64(10) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.60(11) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 121.85(10) . . ? C13 C12 C7 119.64(9) . . ? C11 C12 C7 118.50(9) . . ? C14 C13 C12 119.72(10) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 O1 119.76(9) . . ? C13 C14 C5 121.20(9) . . ? O1 C14 C5 118.96(9) . . ? 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 C14 O1 C2 O3 57.59(11) . . . . ? O1 C2 O3 C4 -53.14(11) . . . . ? C2 O3 C4 O4 -166.68(10) . . . . ? C2 O3 C4 C5 18.76(12) . . . . ? O4 C4 C5 C6 8.96(16) . . . . ? O3 C4 C5 C6 -176.82(9) . . . . ? O4 C4 C5 C14 -164.58(10) . . . . ? O3 C4 C5 C14 9.65(13) . . . . ? C14 C5 C6 C7 0.30(14) . . . . ? C4 C5 C6 C7 -173.19(9) . . . . ? C5 C6 C7 C8 178.64(9) . . . . ? C5 C6 C7 C12 0.36(14) . . . . ? C6 C7 C8 C9 -178.84(10) . . . . ? C12 C7 C8 C9 -0.56(15) . . . . ? C7 C8 C9 C10 -0.30(16) . . . . ? C8 C9 C10 C11 0.38(16) . . . . ? C9 C10 C11 C12 0.41(16) . . . . ? C10 C11 C12 C13 179.03(10) . . . . ? C10 C11 C12 C7 -1.26(15) . . . . ? C6 C7 C12 C13 -0.64(14) . . . . ? C8 C7 C12 C13 -178.96(9) . . . . ? C6 C7 C12 C11 179.64(9) . . . . ? C8 C7 C12 C11 1.32(14) . . . . ? C11 C12 C13 C14 179.96(9) . . . . ? C7 C12 C13 C14 0.25(14) . . . . ? C12 C13 C14 O1 177.09(9) . . . . ? C12 C13 C14 C5 0.41(14) . . . . ? C2 O1 C14 C13 153.69(9) . . . . ? C2 O1 C14 C5 -29.55(12) . . . . ? C6 C5 C14 C13 -0.70(15) . . . . ? C4 C5 C14 C13 172.87(9) . . . . ? C6 C5 C14 O1 -177.40(9) . . . . ? C4 C5 C14 O1 -3.83(13) . . . . ? 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 C2 H21 O4 0.99 2.34 3.1327(13) 136.9 4 C2 H22 O4 0.99 2.57 3.2961(13) 130.2 2 _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.595 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.074 # Attachment 'ppbu.cif' data_ppbu _database_code_depnum_ccdc_archive 'CCDC 846992' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 O3' _chemical_formula_sum 'C16 H16 O3' _chemical_formula_weight 256.29 _chemical_absolute_configuration unk 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 'P c' _symmetry_space_group_name_Hall 'P -2yc' _symmetry_Int_Tables_number 7 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 8.1408(2) _cell_length_b 10.6093(2) _cell_length_c 15.5627(3) _cell_angle_alpha 90.0 _cell_angle_beta 95.408(2) _cell_angle_gamma 90.0 _cell_volume 1338.14(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11994 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 37.2 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method ? _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99408 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29410 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 37.29 _reflns_number_total 12825 _reflns_number_gt 8996 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0500P)^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 constr _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 ? _refine_ls_number_reflns 6738 _refine_ls_number_parameters 343 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 O101 O 0.50610(12) 0.98098(9) 0.15751(6) 0.01978(19) Uani 1 1 d . . . C102 C 0.44964(18) 1.09815(12) 0.12134(9) 0.0211(3) Uani 1 1 d . . . H102 H 0.3398 1.0864 0.0878 0.025 Uiso 1 1 calc R . . O103 O 0.43561(14) 1.18903(10) 0.18921(7) 0.0245(2) Uani 1 1 d . . . O104 O 0.29643(14) 1.23206(10) 0.30199(7) 0.0284(2) Uani 1 1 d . . . C104 C 0.33977(17) 1.15304(13) 0.25222(9) 0.0212(3) Uani 1 1 d . . . C105 C 0.20096(18) 0.96929(14) 0.31745(9) 0.0235(3) Uani 1 1 d . . . H105 H 0.1359 1.0255 0.3476 0.028 Uiso 1 1 calc R . . C106 C 0.19127(18) 0.84328(15) 0.33100(9) 0.0239(3) Uani 1 1 d . . . H106 H 0.1184 0.8119 0.3702 0.029 Uiso 1 1 calc R . . C107 C 0.28931(17) 0.75732(13) 0.28702(8) 0.0197(2) Uani 1 1 d . . . C108 C 0.28301(19) 0.62529(14) 0.29985(9) 0.0231(3) Uani 1 1 d . . . H108 H 0.2092 0.5917 0.3378 0.028 Uiso 1 1 calc R . . C109 C 0.3815(2) 0.54525(14) 0.25851(9) 0.0258(3) Uani 1 1 d . . . H109 H 0.3771 0.4572 0.2691 0.031 Uiso 1 1 calc R . . C110 C 0.48906(19) 0.59210(14) 0.20045(9) 0.0236(3) Uani 1 1 d . . . H110 H 0.5573 0.5357 0.1724 0.028 Uiso 1 1 calc R . . C111 C 0.49569(18) 0.71926(13) 0.18422(9) 0.0202(2) Uani 1 1 d . . . H111 H 0.5665 0.7505 0.1440 0.024 Uiso 1 1 calc R . . C112 C 0.39727(17) 0.80342(12) 0.22742(8) 0.0167(2) Uani 1 1 d . . . C113 C 0.40141(16) 0.93568(13) 0.21387(8) 0.0171(2) Uani 1 1 d . . . C114 C 0.30802(17) 1.01755(13) 0.25833(9) 0.0194(2) Uani 1 1 d . . . C115 C 0.5718(2) 1.14699(14) 0.06284(10) 0.0256(3) Uani 1 1 d . . . H15B H 0.6785 1.1625 0.0972 0.031 Uiso 1 1 calc R . . H15A H 0.5318 1.2285 0.0379 0.031 Uiso 1 1 calc R . . C116 C 0.59908(19) 1.05594(15) -0.01028(9) 0.0253(3) Uani 1 1 d . . . H16B H 0.6506 0.9779 0.0145 0.030 Uiso 1 1 calc R . . H16A H 0.4908 1.0330 -0.0405 0.030 Uiso 1 1 calc R . . C117 C 0.7081(2) 1.11036(17) -0.07555(10) 0.0314(3) Uani 1 1 d . . . H17B H 0.6483 1.1798 -0.1075 0.038 Uiso 1 1 calc R . . H17A H 0.8090 1.1462 -0.0443 0.038 Uiso 1 1 calc R . . C118 C 0.7572(2) 1.0124(2) -0.13960(11) 0.0363(4) Uani 1 1 d . . . H18C H 0.8269 1.0518 -0.1800 0.054 Uiso 1 1 calc R . . H18B H 0.6578 0.9779 -0.1716 0.054 Uiso 1 1 calc R . . H18A H 0.8185 0.9443 -0.1085 0.054 Uiso 1 1 calc R . . O201 O -0.08485(12) 0.48630(9) 0.18187(6) 0.0211(2) Uani 1 1 d . . . C202 C -0.03720(18) 0.37033(13) 0.22327(9) 0.0229(3) Uani 1 1 d . . . H202 H 0.0739 0.3798 0.2560 0.027 Uiso 1 1 calc R . . O203 O -0.03217(14) 0.27136(10) 0.16042(7) 0.0272(2) Uani 1 1 d . . . O204 O 0.10038(15) 0.20825(10) 0.04952(8) 0.0330(3) Uani 1 1 d . . . C204 C 0.06431(18) 0.29462(13) 0.09531(10) 0.0239(3) Uani 1 1 d . . . C205 C 0.21338(18) 0.46129(14) 0.01929(9) 0.0229(3) Uani 1 1 d . . . H205 H 0.2750 0.3982 -0.0068 0.028 Uiso 1 1 calc R . . C206 C 0.22828(18) 0.58429(14) -0.00344(9) 0.0239(3) Uani 1 1 d . . . H206 H 0.3002 0.6066 -0.0457 0.029 Uiso 1 1 calc R . . C207 C 0.13732(17) 0.67993(13) 0.03538(9) 0.0198(2) Uani 1 1 d . . . C208 C 0.1488(2) 0.80811(14) 0.01182(10) 0.0258(3) Uani 1 1 d . . . H208 H 0.2190 0.8317 -0.0309 0.031 Uiso 1 1 calc R . . C209 C 0.0600(2) 0.89878(14) 0.04968(10) 0.0288(3) Uani 1 1 d . . . H209 H 0.0676 0.9842 0.0323 0.035 Uiso 1 1 calc R . . C210 C -0.0431(2) 0.86620(13) 0.11449(10) 0.0262(3) Uani 1 1 d . . . H210 H -0.1030 0.9300 0.1408 0.031 Uiso 1 1 calc R . . C211 C -0.05710(18) 0.74294(13) 0.13958(9) 0.0212(3) Uani 1 1 d . . . H211 H -0.1258 0.7215 0.1835 0.025 Uiso 1 1 calc R . . C212 C 0.03127(17) 0.64797(12) 0.09978(8) 0.0173(2) Uani 1 1 d . . . C213 C 0.01967(16) 0.51842(12) 0.12198(8) 0.0167(2) Uani 1 1 d . . . C214 C 0.10564(17) 0.42749(13) 0.08203(9) 0.0191(2) Uani 1 1 d . . . C215 C -0.1620(2) 0.33496(15) 0.28415(10) 0.0294(3) Uani 1 1 d . . . H25B H -0.1266 0.2559 0.3142 0.035 Uiso 1 1 calc R . . H25A H -0.2693 0.3189 0.2506 0.035 Uiso 1 1 calc R . . C216 C -0.1843(2) 0.43685(16) 0.35096(10) 0.0282(3) Uani 1 1 d . . . H26B H -0.2287 0.5137 0.3211 0.034 Uiso 1 1 calc R . . H26A H -0.0752 0.4582 0.3810 0.034 Uiso 1 1 calc R . . C217 C -0.3001(2) 0.39696(19) 0.41768(10) 0.0350(4) Uani 1 1 d . . . H27B H -0.4027 0.3621 0.3876 0.042 Uiso 1 1 calc R . . H27A H -0.2469 0.3295 0.4544 0.042 Uiso 1 1 calc R . . C218 C -0.3433(2) 0.5062(2) 0.47438(11) 0.0440(5) Uani 1 1 d . . . H28C H -0.4176 0.4768 0.5162 0.066 Uiso 1 1 calc R . . H28B H -0.3980 0.5725 0.4384 0.066 Uiso 1 1 calc R . . H28A H -0.2422 0.5399 0.5052 0.066 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 O101 0.0194(4) 0.0171(4) 0.0233(4) 0.0021(3) 0.0041(4) 0.0009(3) C102 0.0242(7) 0.0158(6) 0.0231(6) 0.0005(5) 0.0009(5) 0.0017(5) O103 0.0283(5) 0.0175(4) 0.0275(5) -0.0020(4) 0.0029(4) -0.0012(4) O104 0.0307(6) 0.0211(5) 0.0332(5) -0.0086(4) 0.0021(5) 0.0027(4) C104 0.0191(6) 0.0178(6) 0.0261(6) -0.0028(5) -0.0017(5) 0.0013(5) C105 0.0191(6) 0.0275(7) 0.0245(6) -0.0085(5) 0.0061(5) -0.0021(5) C106 0.0217(6) 0.0296(7) 0.0212(6) -0.0040(5) 0.0067(5) -0.0060(6) C107 0.0196(6) 0.0220(6) 0.0172(5) 0.0002(5) -0.0003(4) -0.0041(5) C108 0.0253(7) 0.0229(6) 0.0204(6) 0.0033(5) -0.0017(5) -0.0062(5) C109 0.0304(8) 0.0187(6) 0.0264(7) 0.0033(5) -0.0074(6) -0.0018(5) C110 0.0256(7) 0.0182(6) 0.0262(6) -0.0012(5) -0.0022(5) 0.0069(5) C111 0.0208(6) 0.0188(6) 0.0208(6) 0.0008(5) 0.0009(5) 0.0033(5) C112 0.0162(5) 0.0158(5) 0.0179(5) -0.0013(4) -0.0002(4) 0.0006(4) C113 0.0156(5) 0.0169(6) 0.0188(5) -0.0009(4) 0.0019(4) -0.0008(4) C114 0.0182(6) 0.0173(6) 0.0227(6) -0.0046(5) 0.0019(5) -0.0004(5) C115 0.0281(7) 0.0224(6) 0.0265(6) 0.0039(5) 0.0033(6) -0.0028(5) C116 0.0229(7) 0.0298(7) 0.0230(6) 0.0021(5) 0.0016(5) -0.0015(5) C117 0.0298(8) 0.0372(9) 0.0273(7) 0.0054(7) 0.0031(6) -0.0006(7) C118 0.0253(8) 0.0569(12) 0.0267(8) -0.0017(8) 0.0025(6) 0.0023(8) O201 0.0208(5) 0.0177(4) 0.0255(5) 0.0042(4) 0.0054(4) 0.0017(4) C202 0.0236(7) 0.0171(6) 0.0275(6) 0.0041(5) 0.0001(5) -0.0007(5) O203 0.0304(5) 0.0148(4) 0.0356(6) 0.0001(4) -0.0008(4) -0.0037(4) O204 0.0318(6) 0.0181(5) 0.0470(7) -0.0101(5) -0.0065(5) 0.0052(4) C204 0.0204(6) 0.0170(6) 0.0327(7) -0.0018(5) -0.0056(5) 0.0010(5) C205 0.0208(6) 0.0246(7) 0.0232(6) -0.0050(5) 0.0010(5) 0.0042(5) C206 0.0222(7) 0.0281(7) 0.0217(6) -0.0006(5) 0.0030(5) 0.0003(6) C207 0.0194(6) 0.0195(6) 0.0198(5) 0.0011(5) -0.0012(5) 0.0003(5) C208 0.0283(7) 0.0220(6) 0.0258(6) 0.0066(5) -0.0046(6) -0.0039(6) C209 0.0321(8) 0.0170(6) 0.0347(7) 0.0046(6) -0.0110(6) -0.0027(6) C210 0.0306(8) 0.0161(6) 0.0299(7) -0.0033(5) -0.0076(6) 0.0055(5) C211 0.0218(6) 0.0163(6) 0.0251(6) -0.0035(5) -0.0011(5) 0.0051(5) C212 0.0185(6) 0.0143(5) 0.0185(5) -0.0007(4) -0.0013(4) 0.0016(4) C213 0.0156(5) 0.0149(5) 0.0193(6) -0.0017(4) -0.0001(4) 0.0013(4) C214 0.0182(6) 0.0146(5) 0.0241(6) -0.0032(5) -0.0009(5) 0.0019(5) C215 0.0277(8) 0.0267(7) 0.0340(7) 0.0096(6) 0.0036(6) -0.0072(6) C216 0.0218(7) 0.0372(8) 0.0254(7) 0.0089(6) 0.0010(5) -0.0044(6) C217 0.0237(7) 0.0539(11) 0.0269(7) 0.0132(7) 0.0001(6) -0.0080(7) C218 0.0267(9) 0.0809(15) 0.0242(8) 0.0014(8) 0.0019(7) -0.0084(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 O101 C113 1.3666(15) . ? O101 C102 1.4229(16) . ? C102 O103 1.4426(16) . ? C102 C115 1.502(2) . ? C102 H102 1.0000 . ? O103 C104 1.3640(18) . ? O104 C104 1.2159(17) . ? C104 C114 1.465(2) . ? C105 C106 1.357(2) . ? C105 C114 1.4210(19) . ? C105 H105 0.9500 . ? C106 C107 1.428(2) . ? C106 H106 0.9500 . ? C107 C108 1.416(2) . ? C107 C112 1.4233(19) . ? C108 C109 1.369(2) . ? C108 H108 0.9500 . ? C109 C110 1.407(2) . ? C109 H109 0.9500 . ? C110 C111 1.375(2) . ? C110 H110 0.9500 . ? C111 C112 1.4116(19) . ? C111 H111 0.9500 . ? C112 C113 1.4198(19) . ? C113 C114 1.3821(18) . ? C115 C116 1.525(2) . ? C115 H15B 0.9900 . ? C115 H15A 0.9900 . ? C116 C117 1.524(2) . ? C116 H16B 0.9900 . ? C116 H16A 0.9900 . ? C117 C118 1.520(3) . ? C117 H17B 0.9900 . ? C117 H17A 0.9900 . ? C118 H18C 0.9800 . ? C118 H18B 0.9800 . ? C118 H18A 0.9800 . ? O201 C213 1.3631(16) . ? O201 C202 1.4255(17) . ? C202 O203 1.4382(18) . ? C202 C215 1.500(2) . ? C202 H202 1.0000 . ? O203 C204 1.3618(19) . ? O204 C204 1.2137(18) . ? C204 C214 1.468(2) . ? C205 C206 1.360(2) . ? C205 C214 1.419(2) . ? C205 H205 0.9500 . ? C206 C207 1.424(2) . ? C206 H206 0.9500 . ? C207 C208 1.414(2) . ? C207 C212 1.4241(19) . ? C208 C209 1.369(2) . ? C208 H208 0.9500 . ? C209 C210 1.414(2) . ? C209 H209 0.9500 . ? C210 C211 1.373(2) . ? C210 H210 0.9500 . ? C211 C212 1.4143(18) . ? C211 H211 0.9500 . ? C212 C213 1.4226(18) . ? C213 C214 1.3744(18) . ? C215 C216 1.523(2) . ? C215 H25B 0.9900 . ? C215 H25A 0.9900 . ? C216 C217 1.527(2) . ? C216 H26B 0.9900 . ? C216 H26A 0.9900 . ? C217 C218 1.518(3) . ? C217 H27B 0.9900 . ? C217 H27A 0.9900 . ? C218 H28C 0.9800 . ? C218 H28B 0.9800 . ? C218 H28A 0.9800 . ? 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 C113 O101 C102 111.31(10) . . ? O101 C102 O103 109.82(10) . . ? O101 C102 C115 109.48(12) . . ? O103 C102 C115 108.41(11) . . ? O101 C102 H102 109.7 . . ? O103 C102 H102 109.7 . . ? C115 C102 H102 109.7 . . ? C104 O103 C102 115.44(11) . . ? O104 C104 O103 119.01(13) . . ? O104 C104 C114 124.85(13) . . ? O103 C104 C114 115.95(12) . . ? C106 C105 C114 120.26(13) . . ? C106 C105 H105 119.9 . . ? C114 C105 H105 119.9 . . ? C105 C106 C107 120.74(13) . . ? C105 C106 H106 119.6 . . ? C107 C106 H106 119.6 . . ? C108 C107 C112 117.68(13) . . ? C108 C107 C106 122.31(13) . . ? C112 C107 C106 120.01(12) . . ? C109 C108 C107 121.09(14) . . ? C109 C108 H108 119.5 . . ? C107 C108 H108 119.5 . . ? C108 C109 C110 120.67(13) . . ? C108 C109 H109 119.7 . . ? C110 C109 H109 119.7 . . ? C111 C110 C109 120.15(14) . . ? C111 C110 H110 119.9 . . ? C109 C110 H110 119.9 . . ? C110 C111 C112 119.96(13) . . ? C110 C111 H111 120.0 . . ? C112 C111 H111 120.0 . . ? C111 C112 C113 122.14(12) . . ? C111 C112 C107 120.40(12) . . ? C113 C112 C107 117.46(11) . . ? O101 C113 C114 120.40(12) . . ? O101 C113 C112 117.89(11) . . ? C114 C113 C112 121.66(12) . . ? C113 C114 C105 119.84(12) . . ? C113 C114 C104 118.38(12) . . ? C105 C114 C104 121.21(12) . . ? C102 C115 C116 112.65(12) . . ? C102 C115 H15B 109.1 . . ? C116 C115 H15B 109.1 . . ? C102 C115 H15A 109.1 . . ? C116 C115 H15A 109.1 . . ? H15B C115 H15A 107.8 . . ? C117 C116 C115 113.10(13) . . ? C117 C116 H16B 109.0 . . ? C115 C116 H16B 109.0 . . ? C117 C116 H16A 109.0 . . ? C115 C116 H16A 109.0 . . ? H16B C116 H16A 107.8 . . ? C118 C117 C116 112.55(15) . . ? C118 C117 H17B 109.1 . . ? C116 C117 H17B 109.1 . . ? C118 C117 H17A 109.1 . . ? C116 C117 H17A 109.1 . . ? H17B C117 H17A 107.8 . . ? C117 C118 H18C 109.5 . . ? C117 C118 H18B 109.5 . . ? H18C C118 H18B 109.5 . . ? C117 C118 H18A 109.5 . . ? H18C C118 H18A 109.5 . . ? H18B C118 H18A 109.5 . . ? C213 O201 C202 111.34(11) . . ? O201 C202 O203 110.28(11) . . ? O201 C202 C215 109.25(12) . . ? O203 C202 C215 108.13(12) . . ? O201 C202 H202 109.7 . . ? O203 C202 H202 109.7 . . ? C215 C202 H202 109.7 . . ? C204 O203 C202 115.41(10) . . ? O204 C204 O203 119.24(13) . . ? O204 C204 C214 124.81(15) . . ? O203 C204 C214 115.75(12) . . ? C206 C205 C214 119.83(13) . . ? C206 C205 H205 120.1 . . ? C214 C205 H205 120.1 . . ? C205 C206 C207 120.70(13) . . ? C205 C206 H206 119.6 . . ? C207 C206 H206 119.6 . . ? C208 C207 C206 121.72(14) . . ? C208 C207 C212 118.08(13) . . ? C206 C207 C212 120.20(12) . . ? C209 C208 C207 120.91(14) . . ? C209 C208 H208 119.5 . . ? C207 C208 H208 119.5 . . ? C208 C209 C210 120.52(14) . . ? C208 C209 H209 119.7 . . ? C210 C209 H209 119.7 . . ? C211 C210 C209 120.44(14) . . ? C211 C210 H210 119.8 . . ? C209 C210 H210 119.8 . . ? C210 C211 C212 119.65(14) . . ? C210 C211 H211 120.2 . . ? C212 C211 H211 120.2 . . ? C211 C212 C213 122.26(12) . . ? C211 C212 C207 120.38(12) . . ? C213 C212 C207 117.36(12) . . ? O201 C213 C214 120.74(12) . . ? O201 C213 C212 117.88(11) . . ? C214 C213 C212 121.33(12) . . ? C213 C214 C205 120.54(13) . . ? C213 C214 C204 118.49(13) . . ? C205 C214 C204 120.28(12) . . ? C202 C215 C216 112.65(12) . . ? C202 C215 H25B 109.1 . . ? C216 C215 H25B 109.1 . . ? C202 C215 H25A 109.1 . . ? C216 C215 H25A 109.1 . . ? H25B C215 H25A 107.8 . . ? C215 C216 C217 112.88(14) . . ? C215 C216 H26B 109.0 . . ? C217 C216 H26B 109.0 . . ? C215 C216 H26A 109.0 . . ? C217 C216 H26A 109.0 . . ? H26B C216 H26A 107.8 . . ? C218 C217 C216 112.05(16) . . ? C218 C217 H27B 109.2 . . ? C216 C217 H27B 109.2 . . ? C218 C217 H27A 109.2 . . ? C216 C217 H27A 109.2 . . ? H27B C217 H27A 107.9 . . ? C217 C218 H28C 109.5 . . ? C217 C218 H28B 109.5 . . ? H28C C218 H28B 109.5 . . ? C217 C218 H28A 109.5 . . ? H28C C218 H28A 109.5 . . ? H28B C218 H28A 109.5 . . ? 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 C113 O101 C102 O103 58.70(14) . . . . ? C113 O101 C102 C115 177.62(11) . . . . ? O101 C102 O103 C104 -54.83(15) . . . . ? C115 C102 O103 C104 -174.41(12) . . . . ? C102 O103 C104 O104 -166.09(13) . . . . ? C102 O103 C104 C114 18.62(17) . . . . ? C114 C105 C106 C107 0.7(2) . . . . ? C105 C106 C107 C108 179.70(14) . . . . ? C105 C106 C107 C112 -0.8(2) . . . . ? C112 C107 C108 C109 2.1(2) . . . . ? C106 C107 C108 C109 -178.30(13) . . . . ? C107 C108 C109 C110 -1.5(2) . . . . ? C108 C109 C110 C111 -0.4(2) . . . . ? C109 C110 C111 C112 1.5(2) . . . . ? C110 C111 C112 C113 179.06(13) . . . . ? C110 C111 C112 C107 -0.8(2) . . . . ? C108 C107 C112 C111 -0.99(19) . . . . ? C106 C107 C112 C111 179.44(13) . . . . ? C108 C107 C112 C113 179.14(13) . . . . ? C106 C107 C112 C113 -0.43(19) . . . . ? C102 O101 C113 C114 -28.33(17) . . . . ? C102 O101 C113 C112 154.12(12) . . . . ? C111 C112 C113 O101 -0.61(19) . . . . ? C107 C112 C113 O101 179.26(11) . . . . ? C111 C112 C113 C114 -178.13(13) . . . . ? C107 C112 C113 C114 1.74(19) . . . . ? O101 C113 C114 C105 -179.32(12) . . . . ? C112 C113 C114 C105 -1.9(2) . . . . ? O101 C113 C114 C104 -7.9(2) . . . . ? C112 C113 C114 C104 169.59(12) . . . . ? C106 C105 C114 C113 0.6(2) . . . . ? C106 C105 C114 C104 -170.59(14) . . . . ? O104 C104 C114 C113 -162.03(14) . . . . ? O103 C104 C114 C113 12.96(19) . . . . ? O104 C104 C114 C105 9.3(2) . . . . ? O103 C104 C114 C105 -175.71(12) . . . . ? O101 C102 C115 C116 58.78(16) . . . . ? O103 C102 C115 C116 178.57(12) . . . . ? C102 C115 C116 C117 173.72(13) . . . . ? C115 C116 C117 C118 170.69(14) . . . . ? C213 O201 C202 O203 -57.59(14) . . . . ? C213 O201 C202 C215 -176.31(12) . . . . ? O201 C202 O203 C204 54.67(16) . . . . ? C215 C202 O203 C204 174.06(12) . . . . ? C202 O203 C204 O204 166.03(13) . . . . ? C202 O203 C204 C214 -18.81(17) . . . . ? C214 C205 C206 C207 0.3(2) . . . . ? C205 C206 C207 C208 -178.98(14) . . . . ? C205 C206 C207 C212 1.0(2) . . . . ? C206 C207 C208 C209 179.81(13) . . . . ? C212 C207 C208 C209 -0.2(2) . . . . ? C207 C208 C209 C210 1.2(2) . . . . ? C208 C209 C210 C211 -0.8(2) . . . . ? C209 C210 C211 C212 -0.5(2) . . . . ? C210 C211 C212 C213 -178.94(13) . . . . ? C210 C211 C212 C207 1.4(2) . . . . ? C208 C207 C212 C211 -1.09(19) . . . . ? C206 C207 C212 C211 178.89(13) . . . . ? C208 C207 C212 C213 179.27(13) . . . . ? C206 C207 C212 C213 -0.75(19) . . . . ? C202 O201 C213 C214 26.61(17) . . . . ? C202 O201 C213 C212 -155.98(12) . . . . ? C211 C212 C213 O201 2.1(2) . . . . ? C207 C212 C213 O201 -178.26(11) . . . . ? C211 C212 C213 C214 179.49(13) . . . . ? C207 C212 C213 C214 -0.87(19) . . . . ? O201 C213 C214 C205 179.54(12) . . . . ? C212 C213 C214 C205 2.2(2) . . . . ? O201 C213 C214 C204 9.05(19) . . . . ? C212 C213 C214 C204 -168.27(12) . . . . ? C206 C205 C214 C213 -1.9(2) . . . . ? C206 C205 C214 C204 168.40(13) . . . . ? O204 C204 C214 C213 161.65(14) . . . . ? O203 C204 C214 C213 -13.21(19) . . . . ? O204 C204 C214 C205 -8.9(2) . . . . ? O203 C204 C214 C205 176.27(12) . . . . ? O201 C202 C215 C216 -56.90(17) . . . . ? O203 C202 C215 C216 -176.94(12) . . . . ? C202 C215 C216 C217 -175.16(13) . . . . ? C215 C216 C217 C218 -170.48(14) . . . . ? 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 C102 H102 O204 1.00 2.37 3.1778(19) 137.5 1_565 C106 H106 O204 0.95 2.82 3.5897(19) 139.2 2_565 C109 H109 O104 0.95 2.54 3.4737(19) 166.8 1_545 C115 H15B O203 0.99 2.72 3.6768(19) 161.9 1_665 C117 H17A O204 0.99 2.75 3.728(2) 171.2 1_665 C118 H18B O101 0.98 2.86 3.597(2) 132.8 2_574 C202 H202 O104 1.00 2.45 3.2253(19) 133.8 1_545 C208 H208 O104 0.95 2.82 3.610(2) 141.7 2_574 C209 H209 O204 0.95 2.40 3.2998(19) 157.1 1_565 C215 H25A O103 0.99 2.85 3.795(2) 158.9 1_445 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 37.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.476 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.051 # Attachment 'ppc.cif' data_ppc _database_code_depnum_ccdc_archive 'CCDC 846993' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 O5' _chemical_formula_sum 'C17 H16 O5' _chemical_formula_weight 300.30 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.5117(1) _cell_length_b 10.3653(2) _cell_length_c 21.8661(4) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1475.87(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9171 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 37.28 _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method ? _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91902 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31913 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 37.37 _reflns_number_total 4217 _reflns_number_gt 3010 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0560P)^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 constr _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 ? _refine_ls_number_reflns 4217 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.68936(16) 0.34195(11) 0.35734(5) 0.0184(2) Uani 1 1 d . . . C2 C 0.6452(2) 0.21751(15) 0.38075(7) 0.0174(3) Uani 1 1 d . . . H2 H 0.5626 0.2246 0.4192 0.021 Uiso 1 1 calc R . . O3 O 0.53944(17) 0.14041(11) 0.33702(5) 0.0201(2) Uani 1 1 d . . . O4 O 0.23661(18) 0.12166(12) 0.29177(5) 0.0287(3) Uani 1 1 d . . . C4 C 0.3612(2) 0.19275(16) 0.31456(7) 0.0202(3) Uani 1 1 d . . . C5 C 0.1715(2) 0.40024(19) 0.29568(8) 0.0260(4) Uani 1 1 d . . . H5 H 0.0550 0.3528 0.2823 0.031 Uiso 1 1 calc R . . C6 C 0.1698(3) 0.5313(2) 0.29318(8) 0.0286(4) Uani 1 1 d . . . H6 H 0.0525 0.5746 0.2775 0.034 Uiso 1 1 calc R . . C7 C 0.3409(3) 0.60438(17) 0.31364(7) 0.0239(3) Uani 1 1 d . . . C8 C 0.3425(3) 0.74142(19) 0.31325(8) 0.0324(4) Uani 1 1 d . . . H8 H 0.2256 0.7867 0.2986 0.039 Uiso 1 1 calc R . . C9 C 0.5092(3) 0.80944(19) 0.33358(8) 0.0349(5) Uani 1 1 d . . . H9 H 0.5068 0.9011 0.3328 0.042 Uiso 1 1 calc R . . C10 C 0.6836(3) 0.74482(18) 0.35551(8) 0.0303(4) Uani 1 1 d . . . H10 H 0.7986 0.7930 0.3694 0.036 Uiso 1 1 calc R . . C11 C 0.6892(3) 0.61255(16) 0.35706(7) 0.0223(3) Uani 1 1 d . . . H11 H 0.8074 0.5694 0.3722 0.027 Uiso 1 1 calc R . . C12 C 0.5190(2) 0.54054(16) 0.33610(7) 0.0196(3) Uani 1 1 d . . . C13 C 0.5157(2) 0.40372(15) 0.33733(6) 0.0169(3) Uani 1 1 d . . . C14 C 0.3478(2) 0.33348(17) 0.31838(7) 0.0199(3) Uani 1 1 d . . . C15 C 0.8484(2) 0.15374(16) 0.39381(7) 0.0207(3) Uani 1 1 d . . . H15 H 0.9352 0.1509 0.3561 0.025 Uiso 1 1 calc R . . C16 C 0.9637(3) 0.22003(17) 0.44623(8) 0.0281(4) Uani 1 1 d . . . H161 H 1.1122 0.2270 0.4370 0.034 Uiso 1 1 calc R . . H162 H 0.9080 0.3074 0.4540 0.034 Uiso 1 1 calc R . . O17 O 0.92882(19) 0.13694(12) 0.49732(5) 0.0282(3) Uani 1 1 d . . . C18 C 0.9109(3) 0.01007(16) 0.47287(7) 0.0248(4) Uani 1 1 d . . . O19 O 0.80834(19) 0.02675(12) 0.41571(5) 0.0281(3) Uani 1 1 d . . . C20 C 1.1211(3) -0.0491(2) 0.46264(11) 0.0417(5) Uani 1 1 d . . . H201 H 1.2019 0.0069 0.4357 0.063 Uiso 1 1 calc R . . H202 H 1.1056 -0.1341 0.4436 0.063 Uiso 1 1 calc R . . H203 H 1.1917 -0.0584 0.5020 0.063 Uiso 1 1 calc R . . C21 C 0.7747(4) -0.0691(2) 0.51376(9) 0.0417(5) Uani 1 1 d . . . H211 H 0.6419 -0.0258 0.5185 0.063 Uiso 1 1 calc R . . H212 H 0.8398 -0.0788 0.5539 0.063 Uiso 1 1 calc R . . H213 H 0.7537 -0.1545 0.4955 0.063 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 0.0157(5) 0.0149(5) 0.0246(5) 0.0016(4) -0.0025(4) 0.0013(4) C2 0.0201(7) 0.0156(7) 0.0167(6) -0.0005(5) -0.0015(5) -0.0019(6) O3 0.0221(5) 0.0185(6) 0.0197(5) -0.0029(4) -0.0043(4) -0.0002(4) O4 0.0241(6) 0.0348(8) 0.0271(6) -0.0025(5) -0.0025(5) -0.0073(5) C4 0.0179(7) 0.0265(8) 0.0163(6) 0.0012(6) 0.0007(6) -0.0009(6) C5 0.0168(7) 0.0375(10) 0.0238(7) 0.0043(7) -0.0018(6) 0.0037(7) C6 0.0229(7) 0.0393(10) 0.0236(7) 0.0089(8) 0.0015(6) 0.0125(8) C7 0.0278(8) 0.0259(8) 0.0180(7) 0.0062(6) 0.0056(6) 0.0118(7) C8 0.0449(11) 0.0276(9) 0.0248(8) 0.0067(7) 0.0070(8) 0.0192(9) C9 0.0579(13) 0.0180(8) 0.0287(9) 0.0021(7) 0.0097(9) 0.0084(8) C10 0.0460(11) 0.0195(8) 0.0254(8) -0.0030(6) 0.0056(8) -0.0020(7) C11 0.0276(8) 0.0191(8) 0.0203(7) 0.0003(6) 0.0027(6) 0.0020(6) C12 0.0236(7) 0.0184(8) 0.0166(6) 0.0022(6) 0.0029(6) 0.0043(6) C13 0.0160(6) 0.0202(7) 0.0145(6) 0.0014(5) 0.0009(5) 0.0037(5) C14 0.0171(7) 0.0255(8) 0.0170(6) 0.0023(6) 0.0001(6) 0.0011(6) C15 0.0227(7) 0.0176(7) 0.0217(7) -0.0002(6) -0.0050(6) 0.0023(6) C16 0.0298(9) 0.0206(8) 0.0337(8) 0.0011(7) -0.0125(7) 0.0005(7) O17 0.0362(7) 0.0266(7) 0.0220(5) -0.0048(5) -0.0073(5) -0.0030(6) C18 0.0333(8) 0.0218(9) 0.0193(7) 0.0002(6) -0.0088(6) 0.0020(6) O19 0.0440(7) 0.0171(6) 0.0233(5) 0.0008(5) -0.0160(5) 0.0012(5) C20 0.0385(10) 0.0323(12) 0.0542(12) 0.0016(10) -0.0107(9) 0.0102(9) C21 0.0546(13) 0.0431(12) 0.0275(9) 0.0030(8) -0.0043(9) -0.0184(10) _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 C13 1.3714(18) . ? O1 C2 1.4171(19) . ? C2 O3 1.4239(18) . ? C2 C15 1.507(2) . ? C2 H2 1.0000 . ? O3 C4 1.3721(19) . ? O4 C4 1.2039(19) . ? C4 C14 1.464(2) . ? C5 C6 1.360(3) . ? C5 C14 1.429(2) . ? C5 H5 0.9500 . ? C6 C7 1.420(3) . ? C6 H6 0.9500 . ? C7 C8 1.421(3) . ? C7 C12 1.423(2) . ? C8 C9 1.369(3) . ? C8 H8 0.9500 . ? C9 C10 1.403(3) . ? C9 H9 0.9500 . ? C10 C11 1.372(2) . ? C10 H10 0.9500 . ? C11 C12 1.413(2) . ? C11 H11 0.9500 . ? C12 C13 1.419(2) . ? C13 C14 1.377(2) . ? C15 O19 1.425(2) . ? C15 C16 1.533(2) . ? C15 H15 1.0000 . ? C16 O17 1.429(2) . ? C16 H161 0.9900 . ? C16 H162 0.9900 . ? O17 C18 1.424(2) . ? C18 O19 1.4274(19) . ? C18 C21 1.503(3) . ? C18 C20 1.517(3) . ? C20 H201 0.9800 . ? C20 H202 0.9800 . ? C20 H203 0.9800 . ? C21 H211 0.9800 . ? C21 H212 0.9800 . ? C21 H213 0.9800 . ? 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 C13 O1 C2 111.89(12) . . ? O1 C2 O3 111.49(11) . . ? O1 C2 C15 106.84(12) . . ? O3 C2 C15 107.81(12) . . ? O1 C2 H2 110.2 . . ? O3 C2 H2 110.2 . . ? C15 C2 H2 110.2 . . ? C4 O3 C2 115.32(12) . . ? O4 C4 O3 118.44(15) . . ? O4 C4 C14 126.39(15) . . ? O3 C4 C14 115.10(13) . . ? C6 C5 C14 120.27(17) . . ? C6 C5 H5 119.9 . . ? C14 C5 H5 119.9 . . ? C5 C6 C7 120.94(16) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C8 122.50(17) . . ? C6 C7 C12 120.02(16) . . ? C8 C7 C12 117.47(18) . . ? C9 C8 C7 121.26(18) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 120.47(18) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.47(19) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.94(17) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 122.28(14) . . ? C11 C12 C7 120.38(15) . . ? C13 C12 C7 117.33(15) . . ? O1 C13 C14 120.26(14) . . ? O1 C13 C12 117.40(14) . . ? C14 C13 C12 122.33(14) . . ? C13 C14 C5 119.08(15) . . ? C13 C14 C4 119.77(14) . . ? C5 C14 C4 120.71(15) . . ? O19 C15 C2 107.95(13) . . ? O19 C15 C16 104.62(12) . . ? C2 C15 C16 112.05(14) . . ? O19 C15 H15 110.7 . . ? C2 C15 H15 110.7 . . ? C16 C15 H15 110.7 . . ? O17 C16 C15 103.68(13) . . ? O17 C16 H161 111.0 . . ? C15 C16 H161 111.0 . . ? O17 C16 H162 111.0 . . ? C15 C16 H162 111.0 . . ? H161 C16 H162 109.0 . . ? C18 O17 C16 106.03(12) . . ? O17 C18 O19 104.78(13) . . ? O17 C18 C21 109.23(15) . . ? O19 C18 C21 108.11(15) . . ? O17 C18 C20 110.78(15) . . ? O19 C18 C20 110.01(15) . . ? C21 C18 C20 113.53(17) . . ? C15 O19 C18 108.69(12) . . ? C18 C20 H201 109.5 . . ? C18 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? C18 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? C18 C21 H211 109.5 . . ? C18 C21 H212 109.5 . . ? H211 C21 H212 109.5 . . ? C18 C21 H213 109.5 . . ? H211 C21 H213 109.5 . . ? H212 C21 H213 109.5 . . ? 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 C13 O1 C2 O3 55.61(15) . . . . ? C13 O1 C2 C15 173.17(12) . . . . ? O1 C2 O3 C4 -55.68(16) . . . . ? C15 C2 O3 C4 -172.65(12) . . . . ? C2 O3 C4 O4 -159.34(14) . . . . ? C2 O3 C4 C14 23.59(17) . . . . ? C14 C5 C6 C7 -0.8(3) . . . . ? C5 C6 C7 C8 -178.27(16) . . . . ? C5 C6 C7 C12 1.2(3) . . . . ? C6 C7 C8 C9 179.61(16) . . . . ? C12 C7 C8 C9 0.1(2) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C10 C11 C12 C13 -179.26(16) . . . . ? C10 C11 C12 C7 -0.3(2) . . . . ? C6 C7 C12 C11 -179.42(14) . . . . ? C8 C7 C12 C11 0.1(2) . . . . ? C6 C7 C12 C13 -0.5(2) . . . . ? C8 C7 C12 C13 179.03(15) . . . . ? C2 O1 C13 C14 -25.86(19) . . . . ? C2 O1 C13 C12 155.27(13) . . . . ? C11 C12 C13 O1 -2.9(2) . . . . ? C7 C12 C13 O1 178.19(12) . . . . ? C11 C12 C13 C14 178.28(14) . . . . ? C7 C12 C13 C14 -0.7(2) . . . . ? O1 C13 C14 C5 -177.77(13) . . . . ? C12 C13 C14 C5 1.1(2) . . . . ? O1 C13 C14 C4 -5.3(2) . . . . ? C12 C13 C14 C4 173.50(14) . . . . ? C6 C5 C14 C13 -0.3(3) . . . . ? C6 C5 C14 C4 -172.68(15) . . . . ? O4 C4 C14 C13 -170.12(15) . . . . ? O3 C4 C14 C13 6.7(2) . . . . ? O4 C4 C14 C5 2.2(2) . . . . ? O3 C4 C14 C5 179.00(13) . . . . ? O1 C2 C15 O19 -178.27(11) . . . . ? O3 C2 C15 O19 -58.32(15) . . . . ? O1 C2 C15 C16 67.05(16) . . . . ? O3 C2 C15 C16 -173.00(13) . . . . ? O19 C15 C16 O17 -14.90(17) . . . . ? C2 C15 C16 O17 101.80(15) . . . . ? C15 C16 O17 C18 31.06(17) . . . . ? C16 O17 C18 O19 -35.82(17) . . . . ? C16 O17 C18 C21 -151.45(15) . . . . ? C16 O17 C18 C20 82.77(16) . . . . ? C2 C15 O19 C18 -126.13(14) . . . . ? C16 C15 O19 C18 -6.63(18) . . . . ? O17 C18 O19 C15 25.95(17) . . . . ? C21 C18 O19 C15 142.36(15) . . . . ? C20 C18 O19 C15 -93.16(17) . . . . ? 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 C6 H6 O4 0.95 2.47 3.366(2) 158.3 3 C9 H9 O3 0.95 2.49 3.437(2) 173.4 1_565 C10 H10 O19 0.95 2.63 3.307(2) 128.8 1_565 C2 H2 O17 1.00 2.48 3.3720(19) 148.2 4_456 C15 H15 O4 1.00 2.43 3.388(2) 159.4 1_655 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.532 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.060 # Attachment 'ppccl3.cif' data_ppccl3 _database_code_depnum_ccdc_archive 'CCDC 846994' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Cl3 O3' _chemical_formula_sum 'C13 H7 Cl3 O3' _chemical_formula_weight 317.54 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8452(3) _cell_length_b 9.3279(3) _cell_length_c 12.1599(6) _cell_angle_alpha 109.289(4) _cell_angle_beta 99.692(4) _cell_angle_gamma 93.069(4) _cell_volume 612.59(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8802 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 40.8 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method ? _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.746 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98523 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16108 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 40.93 _reflns_number_total 7835 _reflns_number_gt 6261 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0400P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7835 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.003 _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 0.75821(9) 0.54782(6) 0.85839(5) 0.01193(9) Uani 1 1 d . . . C2 C 0.71900(12) 0.70124(8) 0.89455(6) 0.01057(10) Uani 1 1 d . . . H2 H 0.8020 0.7560 0.8518 0.013 Uiso 1 1 calc R . . O3 O 0.47678(9) 0.72043(6) 0.87656(5) 0.01285(9) Uani 1 1 d . . . O4 O 0.14571(10) 0.67111(7) 0.74526(5) 0.01684(10) Uani 1 1 d . . . C4 C 0.33870(12) 0.63651(8) 0.76870(6) 0.01194(11) Uani 1 1 d . . . C5 C 0.44042(12) 0.50749(8) 0.69404(6) 0.01111(11) Uani 1 1 d . . . C6 C 0.32605(12) 0.42056(9) 0.58029(7) 0.01299(11) Uani 1 1 d . . . H6 H 0.1802 0.4457 0.5483 0.016 Uiso 1 1 calc R . . C7 C 0.42369(13) 0.29485(8) 0.51105(6) 0.01275(11) Uani 1 1 d . . . C8 C 0.30923(14) 0.20278(9) 0.39354(7) 0.01646(13) Uani 1 1 d . . . H8 H 0.1616 0.2244 0.3604 0.020 Uiso 1 1 calc R . . C9 C 0.41155(16) 0.08330(10) 0.32820(7) 0.01920(15) Uani 1 1 d . . . H9 H 0.3345 0.0228 0.2498 0.023 Uiso 1 1 calc R . . C10 C 0.63086(16) 0.04912(10) 0.37636(7) 0.01921(14) Uani 1 1 d . . . H10 H 0.6999 -0.0340 0.3300 0.023 Uiso 1 1 calc R . . C11 C 0.74439(14) 0.13502(9) 0.48935(7) 0.01635(13) Uani 1 1 d . . . H11 H 0.8918 0.1112 0.5206 0.020 Uiso 1 1 calc R . . C12 C 0.64345(12) 0.25915(8) 0.55998(6) 0.01226(11) Uani 1 1 d . . . C13 C 0.75784(12) 0.34804(8) 0.67725(6) 0.01245(11) Uani 1 1 d . . . H13 H 0.9037 0.3247 0.7108 0.015 Uiso 1 1 calc R . . C14 C 0.65584(12) 0.46776(8) 0.74155(6) 0.01076(10) Uani 1 1 d . . . C15 C 0.81640(12) 0.77052(8) 1.02902(6) 0.01051(10) Uani 1 1 d . . . Cl1 Cl 1.11654(3) 0.74897(2) 1.052911(15) 0.01282(4) Uani 1 1 d . . . Cl2 Cl 0.77616(3) 0.96615(2) 1.080295(16) 0.01425(4) Uani 1 1 d . . . Cl3 Cl 0.67068(3) 0.67373(2) 1.106075(16) 0.01358(4) Uani 1 1 d . . . 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 0.0138(2) 0.0104(2) 0.0091(2) 0.00092(16) -0.00033(16) 0.00407(16) C2 0.0101(2) 0.0108(3) 0.0104(3) 0.0028(2) 0.00197(19) 0.00311(19) O3 0.00978(19) 0.0145(2) 0.0123(2) 0.00198(17) 0.00129(16) 0.00412(16) O4 0.0113(2) 0.0194(3) 0.0188(3) 0.0056(2) 0.00111(18) 0.00586(18) C4 0.0108(2) 0.0127(3) 0.0124(3) 0.0045(2) 0.0019(2) 0.0023(2) C5 0.0103(2) 0.0117(3) 0.0110(3) 0.0037(2) 0.0013(2) 0.0026(2) C6 0.0115(3) 0.0143(3) 0.0120(3) 0.0043(2) -0.0002(2) 0.0016(2) C7 0.0136(3) 0.0132(3) 0.0104(3) 0.0037(2) 0.0009(2) 0.0003(2) C8 0.0179(3) 0.0171(3) 0.0113(3) 0.0036(2) -0.0019(2) -0.0010(2) C9 0.0252(4) 0.0174(3) 0.0108(3) 0.0014(2) 0.0004(3) -0.0008(3) C10 0.0253(4) 0.0160(3) 0.0135(3) 0.0009(2) 0.0047(3) 0.0035(3) C11 0.0188(3) 0.0150(3) 0.0130(3) 0.0012(2) 0.0037(2) 0.0043(2) C12 0.0135(3) 0.0118(3) 0.0104(3) 0.0026(2) 0.0021(2) 0.0015(2) C13 0.0117(3) 0.0125(3) 0.0113(3) 0.0020(2) 0.0010(2) 0.0033(2) C14 0.0105(2) 0.0111(3) 0.0095(3) 0.0024(2) 0.00107(19) 0.00159(19) C15 0.0107(2) 0.0100(2) 0.0107(3) 0.0027(2) 0.00320(19) 0.00207(19) Cl1 0.00960(6) 0.01427(7) 0.01296(7) 0.00288(5) 0.00137(5) 0.00189(5) Cl2 0.01655(7) 0.00993(7) 0.01549(8) 0.00222(5) 0.00501(6) 0.00320(5) Cl3 0.01390(7) 0.01505(7) 0.01294(7) 0.00598(6) 0.00383(5) 0.00022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.3782(8) . ? O1 C2 1.3954(9) . ? C2 O3 1.4259(9) . ? C2 C15 1.5377(10) . ? C2 H2 1.0000 . ? O3 C4 1.3719(9) . ? O4 C4 1.2039(9) . ? C4 C5 1.4706(10) . ? C5 C6 1.3810(10) . ? C5 C14 1.4153(10) . ? C6 C7 1.4110(11) . ? C6 H6 0.9500 . ? C7 C8 1.4258(10) . ? C7 C12 1.4263(11) . ? C8 C9 1.3702(12) . ? C8 H8 0.9500 . ? C9 C10 1.4150(13) . ? C9 H9 0.9500 . ? C10 C11 1.3707(11) . ? C10 H10 0.9500 . ? C11 C12 1.4189(11) . ? C11 H11 0.9500 . ? C12 C13 1.4165(10) . ? C13 C14 1.3657(10) . ? C13 H13 0.9500 . ? C15 Cl1 1.7628(7) . ? C15 Cl2 1.7657(7) . ? C15 Cl3 1.7787(7) . ? 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 C2 112.95(5) . . ? O1 C2 O3 112.74(6) . . ? O1 C2 C15 107.12(6) . . ? O3 C2 C15 107.07(5) . . ? O1 C2 H2 109.9 . . ? O3 C2 H2 109.9 . . ? C15 C2 H2 109.9 . . ? C4 O3 C2 117.94(6) . . ? O4 C4 O3 118.05(7) . . ? O4 C4 C5 126.13(7) . . ? O3 C4 C5 115.78(6) . . ? C6 C5 C14 119.26(7) . . ? C6 C5 C4 121.46(6) . . ? C14 C5 C4 119.23(6) . . ? C5 C6 C7 120.66(7) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 121.89(7) . . ? C6 C7 C12 119.02(6) . . ? C8 C7 C12 119.09(7) . . ? C9 C8 C7 120.20(7) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.63(7) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 120.48(8) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 120.53(7) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 121.14(7) . . ? C13 C12 C7 119.82(7) . . ? C11 C12 C7 119.04(7) . . ? C14 C13 C12 119.19(7) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 O1 119.37(6) . . ? C13 C14 C5 122.03(6) . . ? O1 C14 C5 118.51(6) . . ? C2 C15 Cl1 107.72(5) . . ? C2 C15 Cl2 109.44(5) . . ? Cl1 C15 Cl2 110.27(4) . . ? C2 C15 Cl3 110.39(5) . . ? Cl1 C15 Cl3 109.59(4) . . ? Cl2 C15 Cl3 109.41(4) . . ? 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 C14 O1 C2 O3 55.76(8) . . . . ? C14 O1 C2 C15 173.29(5) . . . . ? O1 C2 O3 C4 -47.02(8) . . . . ? C15 C2 O3 C4 -164.57(6) . . . . ? C2 O3 C4 O4 -167.17(7) . . . . ? C2 O3 C4 C5 15.07(9) . . . . ? O4 C4 C5 C6 6.92(12) . . . . ? O3 C4 C5 C6 -175.52(6) . . . . ? O4 C4 C5 C14 -170.52(7) . . . . ? O3 C4 C5 C14 7.04(10) . . . . ? C14 C5 C6 C7 -0.98(11) . . . . ? C4 C5 C6 C7 -178.42(7) . . . . ? C5 C6 C7 C8 179.78(7) . . . . ? C5 C6 C7 C12 -0.37(11) . . . . ? C6 C7 C8 C9 178.81(8) . . . . ? C12 C7 C8 C9 -1.04(12) . . . . ? C7 C8 C9 C10 0.32(13) . . . . ? C8 C9 C10 C11 0.09(13) . . . . ? C9 C10 C11 C12 0.25(13) . . . . ? C10 C11 C12 C13 179.44(7) . . . . ? C10 C11 C12 C7 -0.98(12) . . . . ? C6 C7 C12 C13 1.10(11) . . . . ? C8 C7 C12 C13 -179.05(7) . . . . ? C6 C7 C12 C11 -178.49(7) . . . . ? C8 C7 C12 C11 1.35(11) . . . . ? C11 C12 C13 C14 179.14(7) . . . . ? C7 C12 C13 C14 -0.44(11) . . . . ? C12 C13 C14 O1 175.48(6) . . . . ? C12 C13 C14 C5 -0.96(11) . . . . ? C2 O1 C14 C13 149.37(7) . . . . ? C2 O1 C14 C5 -34.06(9) . . . . ? C6 C5 C14 C13 1.69(11) . . . . ? C4 C5 C14 C13 179.18(7) . . . . ? C6 C5 C14 O1 -174.78(6) . . . . ? C4 C5 C14 O1 2.71(10) . . . . ? O1 C2 C15 Cl1 59.21(6) . . . . ? O3 C2 C15 Cl1 -179.61(4) . . . . ? O1 C2 C15 Cl2 179.12(4) . . . . ? O3 C2 C15 Cl2 -59.71(6) . . . . ? O1 C2 C15 Cl3 -60.41(6) . . . . ? O3 C2 C15 Cl3 60.76(6) . . . . ? 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 C2 H2 O4 1.00 2.59 3.2952(9) 127.4 1_655 C8 H8 O4 0.95 2.46 3.3822(10) 162.7 2_566 C9 H9 Cl1 0.95 2.91 3.8064(8) 157.9 1_444 C10 H10 Cl3 0.95 3.13 3.9823(9) 150.9 1_544 C10 H10 Cl2 0.95 3.14 3.6797(9) 117.5 1_544 C13 H13 Cl3 0.95 3.04 3.9502(8) 160.4 2_767 C13 H13 Cl1 0.95 3.19 3.6532(8) 112.2 2_767 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 40.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.632 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.082 # Attachment 'ppd.cif' data_ppd _database_code_depnum_ccdc_archive 'CCDC 846995' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 O3' _chemical_formula_sum 'C15 H14 O3' _chemical_formula_weight 242.26 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.8319(2) _cell_length_b 12.3938(5) _cell_length_c 24.6888(7) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 2396.47(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10516 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 37.26 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method ? _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88822 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35712 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5793 _reflns_number_gt 4557 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0700P)^2^+3.4000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3292 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.1722 _refine_ls_wR_factor_gt 0.1627 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 O101 O 0.4963(4) 0.6346(2) 0.13408(10) 0.0291(7) Uani 1 1 d . . . C102 C 0.5119(6) 0.5816(3) 0.08418(14) 0.0251(9) Uani 1 1 d . . . H102 H 0.6341 0.5616 0.0782 0.030 Uiso 1 1 calc R . . O103 O 0.4077(4) 0.4849(2) 0.08297(11) 0.0237(6) Uani 1 1 d . . . O104 O 0.3836(4) 0.3229(2) 0.11895(12) 0.0338(8) Uani 1 1 d . . . C104 C 0.4347(5) 0.4135(3) 0.12409(16) 0.0214(8) Uani 1 1 d . . . C105 C 0.5176(5) 0.4573(3) 0.17310(14) 0.0179(8) Uani 1 1 d . . . C106 C 0.5544(5) 0.3930(3) 0.21608(16) 0.0240(9) Uani 1 1 d . . . H106 H 0.5312 0.3179 0.2139 0.029 Uiso 1 1 calc R . . C107 C 0.6265(5) 0.4354(3) 0.26407(15) 0.0204(8) Uani 1 1 d . . . C108 C 0.6670(7) 0.3702(4) 0.30911(18) 0.0363(11) Uani 1 1 d . . . H108 H 0.6417 0.2952 0.3082 0.044 Uiso 1 1 calc R . . C109 C 0.7418(6) 0.4135(4) 0.35378(17) 0.0338(11) Uani 1 1 d . . . H109 H 0.7725 0.3682 0.3832 0.041 Uiso 1 1 calc R . . C110 C 0.7737(5) 0.5242(4) 0.35660(16) 0.0251(9) Uani 1 1 d . . . H110 H 0.8240 0.5535 0.3884 0.030 Uiso 1 1 calc R . . C111 C 0.7340(5) 0.5905(3) 0.31472(16) 0.0252(9) Uani 1 1 d . . . H111 H 0.7564 0.6656 0.3175 0.030 Uiso 1 1 calc R . . C112 C 0.6597(5) 0.5486(3) 0.26691(15) 0.0193(8) Uani 1 1 d . . . C113 C 0.6174(6) 0.6138(3) 0.22207(15) 0.0267(9) Uani 1 1 d . . . H113 H 0.6376 0.6893 0.2235 0.032 Uiso 1 1 calc R . . C114 C 0.5480(5) 0.5695(3) 0.17675(15) 0.0226(9) Uani 1 1 d . . . C115 C 0.4533(7) 0.6535(4) 0.03875(16) 0.0336(11) Uani 1 1 d . . . H115 H 0.3286 0.6678 0.0436 0.040 Uiso 1 1 calc R . . C116 C 0.5471(9) 0.7608(4) 0.04061(18) 0.0536(17) Uani 1 1 d . . . H16C H 0.5279 0.7952 0.0758 0.080 Uiso 1 1 calc R . . H16B H 0.5042 0.8079 0.0118 0.080 Uiso 1 1 calc R . . H16A H 0.6696 0.7485 0.0354 0.080 Uiso 1 1 calc R . . C117 C 0.4784(7) 0.5960(4) -0.01513(16) 0.0407(12) Uani 1 1 d . . . H17C H 0.4161 0.5274 -0.0147 0.061 Uiso 1 1 calc R . . H17B H 0.6002 0.5821 -0.0208 0.061 Uiso 1 1 calc R . . H17A H 0.4348 0.6415 -0.0445 0.061 Uiso 1 1 calc R . . O201 O -0.0587(4) 0.3661(3) 0.13112(11) 0.0299(7) Uani 1 1 d . . . C202 C -0.0092(5) 0.4080(3) 0.08006(15) 0.0203(8) Uani 1 1 d . . . H202 H 0.1181 0.4060 0.0772 0.024 Uiso 1 1 calc R . . O203 O -0.0662(5) 0.5172(3) 0.07372(12) 0.0364(9) Uani 1 1 d . . . O204 O -0.0335(7) 0.6822(3) 0.10601(13) 0.0694(16) Uani 1 1 d . . . C204 C -0.0182(7) 0.5872(4) 0.11366(16) 0.0362(12) Uani 1 1 d . . . C205 C 0.0386(5) 0.5367(3) 0.16453(15) 0.0214(8) Uani 1 1 d . . . C206 C 0.1057(6) 0.5980(3) 0.20531(16) 0.0280(10) Uani 1 1 d . . . H206 H 0.1224 0.6731 0.1997 0.034 Uiso 1 1 calc R . . C207 C 0.1506(5) 0.5522(4) 0.25547(15) 0.0210(8) Uani 1 1 d . . . C208 C 0.2239(6) 0.6131(4) 0.29779(16) 0.0329(11) Uani 1 1 d . . . H208 H 0.2406 0.6884 0.2931 0.039 Uiso 1 1 calc R . . C209 C 0.2709(6) 0.5662(5) 0.34484(17) 0.0377(12) Uani 1 1 d . . . H209 H 0.3234 0.6080 0.3725 0.045 Uiso 1 1 calc R . . C210 C 0.2422(7) 0.4564(5) 0.35272(17) 0.0429(14) Uani 1 1 d . . . H210 H 0.2755 0.4238 0.3859 0.051 Uiso 1 1 calc R . . C211 C 0.1677(8) 0.3954(4) 0.31394(18) 0.0484(16) Uani 1 1 d . . . H211 H 0.1464 0.3212 0.3208 0.058 Uiso 1 1 calc R . . C212 C 0.1206(6) 0.4404(4) 0.26288(15) 0.0254(9) Uani 1 1 d . . . C213 C 0.0511(7) 0.3791(4) 0.22109(16) 0.0329(11) Uani 1 1 d . . . H213 H 0.0315 0.3042 0.2263 0.040 Uiso 1 1 calc R . . C214 C 0.0107(5) 0.4256(3) 0.17265(15) 0.0212(8) Uani 1 1 d . . . C215 C -0.0850(5) 0.3412(4) 0.03506(16) 0.0255(9) Uani 1 1 d . . . H215 H -0.2123 0.3433 0.0383 0.031 Uiso 1 1 calc R . . C216 C -0.0264(7) 0.2247(3) 0.04035(17) 0.0337(11) Uani 1 1 d . . . H26C H -0.0603 0.1965 0.0758 0.051 Uiso 1 1 calc R . . H26B H 0.0981 0.2214 0.0369 0.051 Uiso 1 1 calc R . . H26A H -0.0792 0.1812 0.0118 0.051 Uiso 1 1 calc R . . C217 C -0.0344(6) 0.3881(4) -0.01985(15) 0.0300(10) Uani 1 1 d . . . H27C H -0.0735 0.4631 -0.0223 0.045 Uiso 1 1 calc R . . H27B H -0.0872 0.3456 -0.0488 0.045 Uiso 1 1 calc R . . H27A H 0.0901 0.3858 -0.0237 0.045 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 O101 0.0453(18) 0.0224(15) 0.0195(13) 0.0026(12) -0.0056(13) -0.0045(15) C102 0.025(2) 0.032(2) 0.0182(17) -0.0013(17) 0.0018(16) -0.0139(18) O103 0.0226(14) 0.0280(16) 0.0206(13) -0.0007(12) -0.0002(11) -0.0058(12) O104 0.0456(19) 0.0231(16) 0.0326(16) -0.0027(14) -0.0124(15) -0.0046(15) C104 0.0176(18) 0.021(2) 0.0261(18) -0.0044(17) -0.0009(16) 0.0024(16) C105 0.0106(15) 0.023(2) 0.0196(16) -0.0042(15) 0.0044(14) -0.0023(15) C106 0.023(2) 0.0145(19) 0.034(2) -0.0021(16) -0.0045(18) 0.0002(16) C107 0.0137(17) 0.021(2) 0.0266(19) 0.0005(17) 0.0010(15) 0.0007(16) C108 0.049(3) 0.023(2) 0.036(2) 0.003(2) -0.014(2) -0.001(2) C109 0.041(3) 0.036(3) 0.024(2) 0.0094(19) -0.010(2) -0.001(2) C110 0.0191(19) 0.038(3) 0.0184(18) -0.0032(18) -0.0057(16) 0.0049(18) C111 0.030(2) 0.021(2) 0.0253(19) -0.0030(17) 0.0031(17) -0.0049(18) C112 0.0162(17) 0.021(2) 0.0202(17) -0.0005(16) 0.0049(14) 0.0003(16) C113 0.038(2) 0.017(2) 0.025(2) -0.0024(16) 0.0032(19) -0.0079(19) C114 0.0244(19) 0.022(2) 0.0210(18) 0.0017(16) -0.0001(16) -0.0038(17) C115 0.045(3) 0.035(3) 0.0206(18) 0.0046(18) 0.0019(19) -0.020(2) C116 0.092(5) 0.043(3) 0.026(2) 0.013(2) -0.012(3) -0.031(3) C117 0.053(3) 0.048(3) 0.0205(19) 0.001(2) -0.001(2) -0.005(3) O201 0.0347(17) 0.0312(17) 0.0237(14) -0.0070(13) 0.0119(13) -0.0147(14) C202 0.0163(18) 0.022(2) 0.0230(17) -0.0032(16) -0.0009(15) 0.0025(16) O203 0.052(2) 0.0322(18) 0.0245(15) -0.0079(13) -0.0107(14) 0.0208(16) O204 0.152(5) 0.0291(19) 0.0272(16) -0.0037(15) -0.034(2) 0.028(3) C204 0.061(3) 0.027(2) 0.0208(19) -0.0050(17) -0.014(2) 0.018(2) C205 0.0235(18) 0.019(2) 0.0218(17) 0.0013(15) 0.0009(16) 0.0047(16) C206 0.043(3) 0.016(2) 0.025(2) 0.0040(16) -0.0058(19) -0.0033(19) C207 0.0156(17) 0.026(2) 0.0209(18) 0.0019(16) 0.0035(15) 0.0057(16) C208 0.032(2) 0.041(3) 0.025(2) 0.001(2) -0.0029(18) -0.012(2) C209 0.023(2) 0.069(4) 0.0204(19) 0.001(2) -0.0014(17) 0.010(2) C210 0.044(3) 0.069(4) 0.0157(19) 0.011(2) 0.008(2) 0.035(3) C211 0.081(4) 0.040(3) 0.024(2) 0.014(2) 0.020(2) 0.033(3) C212 0.029(2) 0.027(2) 0.0201(18) 0.0045(17) 0.0097(17) 0.0110(19) C213 0.056(3) 0.019(2) 0.024(2) 0.0033(17) 0.019(2) 0.000(2) C214 0.0169(17) 0.022(2) 0.0246(18) -0.0080(16) 0.0106(16) 0.0003(16) C215 0.0115(17) 0.034(2) 0.031(2) -0.0115(19) -0.0041(16) -0.0046(17) C216 0.049(3) 0.027(2) 0.025(2) -0.0076(18) 0.008(2) -0.003(2) C217 0.034(2) 0.034(2) 0.0223(18) -0.0048(18) -0.0066(18) -0.003(2) _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 O101 C114 1.387(5) . ? O101 C102 1.401(4) . ? C102 O103 1.451(5) . ? C102 C115 1.504(6) . ? C102 H102 1.0000 . ? O103 C104 1.363(5) . ? O104 C104 1.199(5) . ? C104 C105 1.477(5) . ? C105 C106 1.358(6) . ? C105 C114 1.414(6) . ? C106 C107 1.414(5) . ? C106 H106 0.9500 . ? C107 C108 1.411(6) . ? C107 C112 1.428(6) . ? C108 C109 1.359(6) . ? C108 H108 0.9500 . ? C109 C110 1.396(6) . ? C109 H109 0.9500 . ? C110 C111 1.357(6) . ? C110 H110 0.9500 . ? C111 C112 1.415(5) . ? C111 H111 0.9500 . ? C112 C113 1.410(6) . ? C113 C114 1.359(5) . ? C113 H113 0.9500 . ? C115 C116 1.520(6) . ? C115 C117 1.522(6) . ? C115 H115 1.0000 . ? C116 H16C 0.9800 . ? C116 H16B 0.9800 . ? C116 H16A 0.9800 . ? C117 H17C 0.9800 . ? C117 H17B 0.9800 . ? C117 H17A 0.9800 . ? O201 C214 1.376(5) . ? O201 C202 1.418(4) . ? C202 O203 1.434(5) . ? C202 C215 1.508(5) . ? C202 H202 1.0000 . ? O203 C204 1.366(5) . ? O204 C204 1.198(6) . ? C204 C205 1.472(5) . ? C205 C206 1.367(6) . ? C205 C214 1.408(6) . ? C206 C207 1.407(5) . ? C206 H206 0.9500 . ? C207 C208 1.411(6) . ? C207 C212 1.417(6) . ? C208 C209 1.350(6) . ? C208 H208 0.9500 . ? C209 C210 1.393(8) . ? C209 H209 0.9500 . ? C210 C211 1.352(8) . ? C210 H210 0.9500 . ? C211 C212 1.427(6) . ? C211 H211 0.9500 . ? C212 C213 1.392(6) . ? C213 C214 1.365(6) . ? C213 H213 0.9500 . ? C215 C216 1.520(6) . ? C215 C217 1.528(6) . ? C215 H215 1.0000 . ? C216 H26C 0.9800 . ? C216 H26B 0.9800 . ? C216 H26A 0.9800 . ? C217 H27C 0.9800 . ? C217 H27B 0.9800 . ? C217 H27A 0.9800 . ? 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 C114 O101 C102 111.7(3) . . ? O101 C102 O103 110.9(3) . . ? O101 C102 C115 110.6(4) . . ? O103 C102 C115 107.6(3) . . ? O101 C102 H102 109.2 . . ? O103 C102 H102 109.2 . . ? C115 C102 H102 109.2 . . ? C104 O103 C102 115.7(3) . . ? O104 C104 O103 118.5(4) . . ? O104 C104 C105 125.3(4) . . ? O103 C104 C105 116.1(3) . . ? C106 C105 C114 119.5(4) . . ? C106 C105 C104 121.2(4) . . ? C114 C105 C104 119.2(4) . . ? C105 C106 C107 121.4(4) . . ? C105 C106 H106 119.3 . . ? C107 C106 H106 119.3 . . ? C108 C107 C106 122.5(4) . . ? C108 C107 C112 118.9(4) . . ? C106 C107 C112 118.6(4) . . ? C109 C108 C107 120.7(4) . . ? C109 C108 H108 119.7 . . ? C107 C108 H108 119.7 . . ? C108 C109 C110 120.4(4) . . ? C108 C109 H109 119.8 . . ? C110 C109 H109 119.8 . . ? C111 C110 C109 121.1(4) . . ? C111 C110 H110 119.5 . . ? C109 C110 H110 119.5 . . ? C110 C111 C112 120.5(4) . . ? C110 C111 H111 119.7 . . ? C112 C111 H111 119.7 . . ? C113 C112 C111 122.8(4) . . ? C113 C112 C107 118.8(3) . . ? C111 C112 C107 118.4(4) . . ? C114 C113 C112 120.6(4) . . ? C114 C113 H113 119.7 . . ? C112 C113 H113 119.7 . . ? C113 C114 O101 120.5(4) . . ? C113 C114 C105 121.1(4) . . ? O101 C114 C105 118.3(3) . . ? C102 C115 C116 110.4(4) . . ? C102 C115 C117 109.6(4) . . ? C116 C115 C117 112.0(4) . . ? C102 C115 H115 108.3 . . ? C116 C115 H115 108.3 . . ? C117 C115 H115 108.3 . . ? C115 C116 H16C 109.5 . . ? C115 C116 H16B 109.5 . . ? H16C C116 H16B 109.5 . . ? C115 C116 H16A 109.5 . . ? H16C C116 H16A 109.5 . . ? H16B C116 H16A 109.5 . . ? C115 C117 H17C 109.5 . . ? C115 C117 H17B 109.5 . . ? H17C C117 H17B 109.5 . . ? C115 C117 H17A 109.5 . . ? H17C C117 H17A 109.5 . . ? H17B C117 H17A 109.5 . . ? C214 O201 C202 111.0(3) . . ? O201 C202 O203 111.0(3) . . ? O201 C202 C215 110.2(3) . . ? O203 C202 C215 108.4(3) . . ? O201 C202 H202 109.1 . . ? O203 C202 H202 109.1 . . ? C215 C202 H202 109.1 . . ? C204 O203 C202 115.8(3) . . ? O204 C204 O203 118.9(4) . . ? O204 C204 C205 125.6(4) . . ? O203 C204 C205 115.4(4) . . ? C206 C205 C214 119.9(4) . . ? C206 C205 C204 120.6(4) . . ? C214 C205 C204 119.3(4) . . ? C205 C206 C207 121.3(4) . . ? C205 C206 H206 119.3 . . ? C207 C206 H206 119.3 . . ? C206 C207 C208 122.5(4) . . ? C206 C207 C212 117.8(4) . . ? C208 C207 C212 119.7(4) . . ? C209 C208 C207 121.2(5) . . ? C209 C208 H208 119.4 . . ? C207 C208 H208 119.4 . . ? C208 C209 C210 119.8(5) . . ? C208 C209 H209 120.1 . . ? C210 C209 H209 120.1 . . ? C211 C210 C209 121.1(4) . . ? C211 C210 H210 119.4 . . ? C209 C210 H210 119.4 . . ? C210 C211 C212 121.3(5) . . ? C210 C211 H211 119.4 . . ? C212 C211 H211 119.4 . . ? C213 C212 C207 120.2(4) . . ? C213 C212 C211 122.9(4) . . ? C207 C212 C211 116.9(4) . . ? C214 C213 C212 120.7(4) . . ? C214 C213 H213 119.7 . . ? C212 C213 H213 119.7 . . ? C213 C214 O201 121.2(4) . . ? C213 C214 C205 120.1(4) . . ? O201 C214 C205 118.7(4) . . ? C202 C215 C216 109.8(3) . . ? C202 C215 C217 110.0(3) . . ? C216 C215 C217 111.1(4) . . ? C202 C215 H215 108.6 . . ? C216 C215 H215 108.6 . . ? C217 C215 H215 108.6 . . ? C215 C216 H26C 109.5 . . ? C215 C216 H26B 109.5 . . ? H26C C216 H26B 109.5 . . ? C215 C216 H26A 109.5 . . ? H26C C216 H26A 109.5 . . ? H26B C216 H26A 109.5 . . ? C215 C217 H27C 109.5 . . ? C215 C217 H27B 109.5 . . ? H27C C217 H27B 109.5 . . ? C215 C217 H27A 109.5 . . ? H27C C217 H27A 109.5 . . ? H27B C217 H27A 109.5 . . ? 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 C114 O101 C102 O103 60.1(4) . . . . ? C114 O101 C102 C115 179.4(4) . . . . ? O101 C102 O103 C104 -54.2(4) . . . . ? C115 C102 O103 C104 -175.3(3) . . . . ? C102 O103 C104 O104 -163.0(4) . . . . ? C102 O103 C104 C105 20.2(5) . . . . ? O104 C104 C105 C106 5.0(6) . . . . ? O103 C104 C105 C106 -178.4(3) . . . . ? O104 C104 C105 C114 -170.4(4) . . . . ? O103 C104 C105 C114 6.2(5) . . . . ? C114 C105 C106 C107 -1.6(6) . . . . ? C104 C105 C106 C107 -177.0(3) . . . . ? C105 C106 C107 C108 -179.5(4) . . . . ? C105 C106 C107 C112 0.4(6) . . . . ? C106 C107 C108 C109 177.6(4) . . . . ? C112 C107 C108 C109 -2.3(7) . . . . ? C107 C108 C109 C110 2.5(8) . . . . ? C108 C109 C110 C111 -1.2(7) . . . . ? C109 C110 C111 C112 -0.3(7) . . . . ? C110 C111 C112 C113 -179.4(4) . . . . ? C110 C111 C112 C107 0.4(6) . . . . ? C108 C107 C112 C113 -179.3(4) . . . . ? C106 C107 C112 C113 0.8(6) . . . . ? C108 C107 C112 C111 0.8(6) . . . . ? C106 C107 C112 C111 -179.1(4) . . . . ? C111 C112 C113 C114 179.2(4) . . . . ? C107 C112 C113 C114 -0.7(6) . . . . ? C112 C113 C114 O101 175.8(4) . . . . ? C112 C113 C114 C105 -0.5(6) . . . . ? C102 O101 C114 C113 149.5(4) . . . . ? C102 O101 C114 C105 -34.0(5) . . . . ? C106 C105 C114 C113 1.7(6) . . . . ? C104 C105 C114 C113 177.2(4) . . . . ? C106 C105 C114 O101 -174.7(4) . . . . ? C104 C105 C114 O101 0.8(5) . . . . ? O101 C102 C115 C116 53.9(5) . . . . ? O103 C102 C115 C116 175.2(4) . . . . ? O101 C102 C115 C117 177.7(4) . . . . ? O103 C102 C115 C117 -61.1(5) . . . . ? C214 O201 C202 O203 -60.5(4) . . . . ? C214 O201 C202 C215 179.5(3) . . . . ? O201 C202 O203 C204 54.4(5) . . . . ? C215 C202 O203 C204 175.6(4) . . . . ? C202 O203 C204 O204 166.2(5) . . . . ? C202 O203 C204 C205 -17.6(6) . . . . ? O204 C204 C205 C206 -10.7(9) . . . . ? O203 C204 C205 C206 173.4(4) . . . . ? O204 C204 C205 C214 164.2(6) . . . . ? O203 C204 C205 C214 -11.7(6) . . . . ? C214 C205 C206 C207 1.0(7) . . . . ? C204 C205 C206 C207 175.9(4) . . . . ? C205 C206 C207 C208 178.4(4) . . . . ? C205 C206 C207 C212 -1.3(6) . . . . ? C206 C207 C208 C209 -177.8(4) . . . . ? C212 C207 C208 C209 1.9(7) . . . . ? C207 C208 C209 C210 -2.0(7) . . . . ? C208 C209 C210 C211 0.0(7) . . . . ? C209 C210 C211 C212 2.0(8) . . . . ? C206 C207 C212 C213 0.9(6) . . . . ? C208 C207 C212 C213 -178.9(4) . . . . ? C206 C207 C212 C211 179.7(4) . . . . ? C208 C207 C212 C211 0.0(6) . . . . ? C210 C211 C212 C213 176.9(5) . . . . ? C210 C211 C212 C207 -1.9(7) . . . . ? C207 C212 C213 C214 -0.1(7) . . . . ? C211 C212 C213 C214 -178.9(4) . . . . ? C212 C213 C214 O201 -179.7(4) . . . . ? C212 C213 C214 C205 -0.3(6) . . . . ? C202 O201 C214 C213 -149.1(4) . . . . ? C202 O201 C214 C205 31.4(5) . . . . ? C206 C205 C214 C213 -0.2(6) . . . . ? C204 C205 C214 C213 -175.2(4) . . . . ? C206 C205 C214 O201 179.3(4) . . . . ? C204 C205 C214 O201 4.3(6) . . . . ? O201 C202 C215 C216 -58.7(4) . . . . ? O203 C202 C215 C216 179.7(3) . . . . ? O201 C202 C215 C217 178.8(3) . . . . ? O203 C202 C215 C217 57.2(4) . . . . ? 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 C108 H108 O101 0.95 2.68 3.483(6) 143.0 3_645 C111 H111 O104 0.95 2.73 3.439(5) 131.9 3_655 C102 H102 O203 1.00 2.41 3.409(6) 174.0 1_655 C117 H17A O204 0.98 2.67 3.550(6) 149.2 4_565 C211 H211 O204 0.95 2.65 3.463(6) 144.1 3_545 C202 H202 O103 1.00 2.47 3.402(5) 154.2 . C202 H202 O104 1.00 2.54 3.391(5) 142.9 . C217 H27B O104 0.98 2.72 3.638(5) 155.8 4_455 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.347 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.057 # Attachment 'ppet.cif' data_ppet _database_code_depnum_ccdc_archive 'CCDC 846996' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 O3' _chemical_formula_sum 'C14 H12 O3' _chemical_formula_weight 228.24 _chemical_absolute_configuration ad 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 orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 7.5217(2) _cell_length_b 15.7302(4) _cell_length_c 9.0870(2) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1075.15(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7907 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 37.2 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method ? _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99408 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21092 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 37.39 _reflns_number_total 5368 _reflns_number_gt 4080 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0448P)^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 constr _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 0.3(6) _refine_ls_number_reflns 5368 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.27705(11) 0.11106(4) 0.19554(9) 0.01455(15) Uani 1 1 d . . . C2 C 0.30021(15) 0.12982(6) 0.04401(12) 0.01436(19) Uani 1 1 d . . . H2 H 0.1820 0.1308 -0.0063 0.017 Uiso 1 1 calc R . . O3 O 0.38960(11) 0.20979(5) 0.02192(9) 0.01565(16) Uani 1 1 d . . . O4 O 0.35888(12) 0.34878(5) 0.05142(10) 0.01843(17) Uani 1 1 d . . . C4 C 0.32369(14) 0.27849(7) 0.09602(12) 0.01323(19) Uani 1 1 d . . . C5 C 0.16393(14) 0.32628(6) 0.32337(12) 0.01357(19) Uani 1 1 d . . . H5 H 0.1751 0.3837 0.2922 0.016 Uiso 1 1 calc R . . C6 C 0.08865(15) 0.30840(7) 0.45601(13) 0.01466(19) Uani 1 1 d . . . H6 H 0.0478 0.3535 0.5167 0.018 Uiso 1 1 calc R . . C7 C 0.07034(14) 0.22285(6) 0.50487(11) 0.01228(18) Uani 1 1 d . . . C8 C -0.00768(15) 0.20251(7) 0.64298(12) 0.0156(2) Uani 1 1 d . . . H8 H -0.0492 0.2469 0.7051 0.019 Uiso 1 1 calc R . . C9 C -0.02370(15) 0.11939(7) 0.68763(13) 0.0169(2) Uani 1 1 d . . . H9 H -0.0768 0.1069 0.7800 0.020 Uiso 1 1 calc R . . C10 C 0.03772(15) 0.05270(7) 0.59799(13) 0.0166(2) Uani 1 1 d . . . H10 H 0.0258 -0.0045 0.6300 0.020 Uiso 1 1 calc R . . C11 C 0.11475(14) 0.06993(7) 0.46439(13) 0.01468(19) Uani 1 1 d . . . H11 H 0.1566 0.0246 0.4046 0.018 Uiso 1 1 calc R . . C12 C 0.13218(14) 0.15509(7) 0.41503(11) 0.01219(18) Uani 1 1 d . . . C13 C 0.21007(14) 0.17631(6) 0.27755(12) 0.01176(18) Uani 1 1 d . . . C14 C 0.22593(14) 0.25953(6) 0.23136(11) 0.01218(18) Uani 1 1 d . . . C15 C 0.41364(16) 0.05996(7) -0.02000(13) 0.0170(2) Uani 1 1 d . . . H151 H 0.3477 0.0056 -0.0132 0.020 Uiso 1 1 calc R . . H152 H 0.5227 0.0543 0.0402 0.020 Uiso 1 1 calc R . . C16 C 0.46693(16) 0.07444(7) -0.17922(13) 0.0192(2) Uani 1 1 d . . . H161 H 0.5400 0.0267 -0.2132 0.029 Uiso 1 1 calc R . . H162 H 0.5352 0.1273 -0.1869 0.029 Uiso 1 1 calc R . . H163 H 0.3599 0.0786 -0.2403 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 0.0210(4) 0.0106(3) 0.0120(3) -0.0012(3) 0.0029(3) 0.0012(3) C2 0.0186(5) 0.0129(4) 0.0117(4) -0.0015(4) 0.0023(4) -0.0017(4) O3 0.0193(4) 0.0123(3) 0.0154(4) -0.0010(3) 0.0052(3) -0.0010(3) O4 0.0238(4) 0.0135(3) 0.0181(4) 0.0017(3) 0.0034(3) -0.0018(3) C4 0.0138(5) 0.0135(4) 0.0124(4) -0.0005(3) -0.0010(4) 0.0004(4) C5 0.0167(5) 0.0093(4) 0.0147(5) -0.0006(3) -0.0002(4) 0.0007(3) C6 0.0179(5) 0.0114(4) 0.0146(4) -0.0028(3) 0.0011(4) 0.0007(4) C7 0.0138(5) 0.0120(4) 0.0111(4) -0.0009(3) -0.0001(4) -0.0004(3) C8 0.0172(5) 0.0157(5) 0.0138(4) -0.0028(4) 0.0014(4) -0.0015(4) C9 0.0195(5) 0.0190(5) 0.0123(4) 0.0003(4) 0.0019(4) -0.0021(4) C10 0.0205(5) 0.0130(4) 0.0164(5) 0.0012(4) 0.0008(4) -0.0021(4) C11 0.0191(5) 0.0106(4) 0.0143(4) -0.0010(3) 0.0002(4) -0.0006(4) C12 0.0130(4) 0.0118(4) 0.0118(4) -0.0010(3) 0.0000(4) -0.0003(3) C13 0.0130(4) 0.0110(4) 0.0112(4) -0.0020(3) -0.0003(4) -0.0001(3) C14 0.0134(5) 0.0114(4) 0.0117(4) 0.0002(3) -0.0001(4) 0.0002(3) C15 0.0230(5) 0.0144(4) 0.0136(5) -0.0008(4) 0.0025(4) 0.0024(4) C16 0.0234(6) 0.0206(5) 0.0138(5) -0.0026(4) 0.0033(4) 0.0040(4) _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 C13 1.3648(12) . ? O1 C2 1.4190(14) . ? C2 O3 1.4403(13) . ? C2 C15 1.5080(15) . ? C2 H2 1.0000 . ? O3 C4 1.3664(13) . ? O4 C4 1.2069(13) . ? C4 C14 1.4636(15) . ? C5 C6 1.3610(16) . ? C5 C14 1.4208(14) . ? C5 H5 0.9500 . ? C6 C7 1.4238(15) . ? C6 H6 0.9500 . ? C7 C12 1.4208(14) . ? C7 C8 1.4219(16) . ? C8 C9 1.3742(15) . ? C8 H8 0.9500 . ? C9 C10 1.4062(16) . ? C9 H9 0.9500 . ? C10 C11 1.3721(17) . ? C10 H10 0.9500 . ? C11 C12 1.4189(15) . ? C11 H11 0.9500 . ? C12 C13 1.4197(15) . ? C13 C14 1.3799(13) . ? C15 C16 1.5186(16) . ? C15 H151 0.9900 . ? C15 H152 0.9900 . ? C16 H161 0.9800 . ? C16 H162 0.9800 . ? C16 H163 0.9800 . ? 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 C13 O1 C2 114.75(8) . . ? O1 C2 O3 111.98(8) . . ? O1 C2 C15 106.99(8) . . ? O3 C2 C15 108.58(9) . . ? O1 C2 H2 109.7 . . ? O3 C2 H2 109.7 . . ? C15 C2 H2 109.7 . . ? C4 O3 C2 116.92(8) . . ? O4 C4 O3 118.65(10) . . ? O4 C4 C14 125.39(10) . . ? O3 C4 C14 115.80(9) . . ? C6 C5 C14 120.34(9) . . ? C6 C5 H5 119.8 . . ? C14 C5 H5 119.8 . . ? C5 C6 C7 120.77(10) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C12 C7 C8 118.25(9) . . ? C12 C7 C6 119.88(10) . . ? C8 C7 C6 121.86(10) . . ? C9 C8 C7 120.72(10) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.66(11) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 120.26(10) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.34(10) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 122.57(9) . . ? C11 C12 C7 119.76(9) . . ? C13 C12 C7 117.67(9) . . ? O1 C13 C14 121.03(9) . . ? O1 C13 C12 117.13(8) . . ? C14 C13 C12 121.76(9) . . ? C13 C14 C5 119.58(10) . . ? C13 C14 C4 119.49(9) . . ? C5 C14 C4 120.58(9) . . ? C2 C15 C16 114.05(9) . . ? C2 C15 H151 108.7 . . ? C16 C15 H151 108.7 . . ? C2 C15 H152 108.7 . . ? C16 C15 H152 108.7 . . ? H151 C15 H152 107.6 . . ? C15 C16 H161 109.5 . . ? C15 C16 H162 109.5 . . ? H161 C16 H162 109.5 . . ? C15 C16 H163 109.5 . . ? H161 C16 H163 109.5 . . ? H162 C16 H163 109.5 . . ? 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 C13 O1 C2 O3 47.85(12) . . . . ? C13 O1 C2 C15 166.70(9) . . . . ? O1 C2 O3 C4 -50.35(13) . . . . ? C15 C2 O3 C4 -168.26(9) . . . . ? C2 O3 C4 O4 -159.33(10) . . . . ? C2 O3 C4 C14 25.17(14) . . . . ? C14 C5 C6 C7 -0.10(17) . . . . ? C5 C6 C7 C12 0.42(16) . . . . ? C5 C6 C7 C8 179.95(11) . . . . ? C12 C7 C8 C9 -0.42(16) . . . . ? C6 C7 C8 C9 -179.96(11) . . . . ? C7 C8 C9 C10 0.38(17) . . . . ? C8 C9 C10 C11 0.03(18) . . . . ? C9 C10 C11 C12 -0.38(17) . . . . ? C10 C11 C12 C13 -179.71(10) . . . . ? C10 C11 C12 C7 0.33(16) . . . . ? C8 C7 C12 C11 0.07(15) . . . . ? C6 C7 C12 C11 179.62(11) . . . . ? C8 C7 C12 C13 -179.89(10) . . . . ? C6 C7 C12 C13 -0.34(14) . . . . ? C2 O1 C13 C14 -22.49(15) . . . . ? C2 O1 C13 C12 160.66(9) . . . . ? C11 C12 C13 O1 -3.17(15) . . . . ? C7 C12 C13 O1 176.79(9) . . . . ? C11 C12 C13 C14 -179.99(10) . . . . ? C7 C12 C13 C14 -0.04(15) . . . . ? O1 C13 C14 C5 -176.36(10) . . . . ? C12 C13 C14 C5 0.35(16) . . . . ? O1 C13 C14 C4 -3.05(16) . . . . ? C12 C13 C14 C4 173.66(10) . . . . ? C6 C5 C14 C13 -0.28(16) . . . . ? C6 C5 C14 C4 -173.52(11) . . . . ? O4 C4 C14 C13 -173.48(11) . . . . ? O3 C4 C14 C13 1.68(15) . . . . ? O4 C4 C14 C5 -0.24(17) . . . . ? O3 C4 C14 C5 174.92(10) . . . . ? O1 C2 C15 C16 -174.37(9) . . . . ? O3 C2 C15 C16 -53.34(13) . . . . ? 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 C2 H2 O4 1.00 2.51 3.3373(15) 140.2 3_455 C9 H9 O4 0.95 2.61 3.4581(14) 149.1 3_456 C10 H10 O4 0.95 2.57 3.3277(13) 137.3 4_545 C16 H161 O1 0.98 2.70 3.6766(14) 176.3 2_654 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.445 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.061 # Attachment 'ppp97.cif' data_ppp97 _database_code_depnum_ccdc_archive 'CCDC 846997' _publ_section_title_footnote ; ? ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 O3' _chemical_formula_sum 'C13 H10 O3' _chemical_formula_weight 214.21 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7746(4) _cell_length_b 15.6168(5) _cell_length_c 6.1107(2) _cell_angle_alpha 90.0 _cell_angle_beta 98.201(3) _cell_angle_gamma 90.0 _cell_volume 1017.70(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3394 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 37.0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method ? _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99226 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11513 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 37.10 _reflns_number_total 5059 _reflns_number_gt 2714 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _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^)+(0.0290P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5059 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.60719(6) 0.44160(4) 0.77151(11) 0.01716(16) Uani 1 1 d . . . C2 C 0.71563(9) 0.39087(6) 0.76313(16) 0.0169(2) Uani 1 1 d . . . H2 H 0.7040 0.3331 0.8276 0.020 Uiso 1 1 calc R . . O3 O 0.74105(6) 0.38206(4) 0.53811(11) 0.01835(16) Uani 1 1 d . . . O4 O 0.66918(7) 0.32118(4) 0.21761(12) 0.02161(17) Uani 1 1 d . . . C4 C 0.64587(10) 0.35100(6) 0.38917(17) 0.01548(19) Uani 1 1 d . . . C5 C 0.51921(9) 0.36177(6) 0.45040(15) 0.01404(19) Uani 1 1 d . . . C6 C 0.41593(9) 0.33248(6) 0.31221(16) 0.01500(19) Uani 1 1 d . . . H6 H 0.4269 0.3018 0.1822 0.018 Uiso 1 1 calc R . . C7 C 0.29389(10) 0.34760(6) 0.36167(16) 0.01466(19) Uani 1 1 d . . . C8 C 0.18612(10) 0.31739(6) 0.22196(16) 0.0173(2) Uani 1 1 d . . . H8 H 0.1956 0.2872 0.0904 0.021 Uiso 1 1 calc R . . C9 C 0.06903(10) 0.33132(6) 0.27517(17) 0.0200(2) Uani 1 1 d . . . H9 H -0.0023 0.3098 0.1823 0.024 Uiso 1 1 calc R . . C10 C 0.05359(10) 0.37762(6) 0.46755(17) 0.0210(2) Uani 1 1 d . . . H10 H -0.0284 0.3878 0.5020 0.025 Uiso 1 1 calc R . . C11 C 0.15549(10) 0.40806(6) 0.60524(17) 0.0192(2) Uani 1 1 d . . . H11 H 0.1434 0.4390 0.7345 0.023 Uiso 1 1 calc R . . C12 C 0.27900(9) 0.39395(6) 0.55702(16) 0.01521(19) Uani 1 1 d . . . C13 C 0.38644(10) 0.42424(6) 0.69744(16) 0.0162(2) Uani 1 1 d . . . H13 H 0.3774 0.4552 0.8280 0.019 Uiso 1 1 calc R . . C14 C 0.50305(9) 0.40841(6) 0.64291(16) 0.01445(19) Uani 1 1 d . . . C15 C 0.82581(10) 0.43469(7) 0.89206(17) 0.0207(2) Uani 1 1 d . . . H151 H 0.8114 0.4416 1.0458 0.031 Uiso 1 1 calc R . . H152 H 0.8370 0.4911 0.8273 0.031 Uiso 1 1 calc R . . H153 H 0.9013 0.4001 0.8876 0.031 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 0.0132(4) 0.0187(3) 0.0192(4) -0.0040(3) 0.0009(3) -0.0001(3) C2 0.0166(5) 0.0186(4) 0.0158(5) 0.0017(4) 0.0030(4) 0.0023(4) O3 0.0145(4) 0.0238(4) 0.0171(4) -0.0006(3) 0.0038(3) -0.0006(3) O4 0.0222(4) 0.0259(4) 0.0185(4) -0.0017(3) 0.0087(3) 0.0011(3) C4 0.0146(5) 0.0150(4) 0.0171(5) 0.0032(4) 0.0033(4) 0.0004(4) C5 0.0152(5) 0.0135(4) 0.0140(4) 0.0014(3) 0.0044(4) 0.0014(3) C6 0.0181(5) 0.0145(4) 0.0127(4) -0.0007(3) 0.0034(4) 0.0010(4) C7 0.0150(5) 0.0139(4) 0.0150(5) 0.0018(4) 0.0020(4) 0.0008(3) C8 0.0183(5) 0.0168(4) 0.0162(5) -0.0004(4) 0.0000(4) 0.0012(4) C9 0.0161(5) 0.0197(5) 0.0224(5) 0.0020(4) -0.0033(4) 0.0001(4) C10 0.0147(5) 0.0229(5) 0.0259(6) 0.0020(4) 0.0049(4) 0.0021(4) C11 0.0168(5) 0.0207(5) 0.0210(5) -0.0027(4) 0.0050(4) 0.0017(4) C12 0.0144(5) 0.0151(4) 0.0164(5) 0.0009(4) 0.0030(4) 0.0010(4) C13 0.0169(5) 0.0169(5) 0.0151(5) -0.0038(4) 0.0037(4) 0.0003(4) C14 0.0141(5) 0.0141(4) 0.0148(5) 0.0005(4) 0.0009(4) -0.0006(3) C15 0.0171(5) 0.0232(5) 0.0209(5) 0.0006(4) 0.0000(4) -0.0004(4) _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 1.3761(11) . ? O1 C2 1.4187(12) . ? C2 O3 1.4464(12) . ? C2 C15 1.4938(14) . ? C2 H2 1.0000 . ? O3 C4 1.3597(12) . ? O4 C4 1.2059(12) . ? C4 C5 1.4752(14) . ? C5 C6 1.3758(13) . ? C5 C14 1.4153(13) . ? C6 C7 1.4105(14) . ? C6 H6 0.9500 . ? C7 C8 1.4202(14) . ? C7 C12 1.4245(13) . ? C8 C9 1.3644(14) . ? C8 H8 0.9500 . ? C9 C10 1.4100(15) . ? C9 H9 0.9500 . ? C10 C11 1.3696(14) . ? C10 H10 0.9500 . ? C11 C12 1.4206(14) . ? C11 H11 0.9500 . ? C12 C13 1.4202(14) . ? C13 C14 1.3675(14) . ? C13 H13 0.9500 . ? C15 H151 0.9800 . ? C15 H152 0.9800 . ? C15 H153 0.9800 . ? 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 C2 112.19(7) . . ? O1 C2 O3 110.86(7) . . ? O1 C2 C15 108.77(8) . . ? O3 C2 C15 107.52(8) . . ? O1 C2 H2 109.9 . . ? O3 C2 H2 109.9 . . ? C15 C2 H2 109.9 . . ? C4 O3 C2 116.31(8) . . ? O4 C4 O3 119.27(9) . . ? O4 C4 C5 125.41(9) . . ? O3 C4 C5 115.23(9) . . ? C6 C5 C14 119.78(9) . . ? C6 C5 C4 120.20(9) . . ? C14 C5 C4 119.83(9) . . ? C5 C6 C7 120.66(9) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 121.52(9) . . ? C6 C7 C12 118.98(9) . . ? C8 C7 C12 119.50(9) . . ? C9 C8 C7 120.55(10) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.23(10) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.70(10) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.75(10) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 122.00(9) . . ? C13 C12 C7 119.74(9) . . ? C11 C12 C7 118.26(9) . . ? C14 C13 C12 119.38(9) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 O1 119.69(9) . . ? C13 C14 C5 121.45(9) . . ? O1 C14 C5 118.78(9) . . ? C2 C15 H151 109.5 . . ? C2 C15 H152 109.5 . . ? H151 C15 H152 109.5 . . ? C2 C15 H153 109.5 . . ? H151 C15 H153 109.5 . . ? H152 C15 H153 109.5 . . ? 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 C14 O1 C2 O3 57.60(10) . . . . ? C14 O1 C2 C15 175.61(8) . . . . ? O1 C2 O3 C4 -54.97(10) . . . . ? C15 C2 O3 C4 -173.74(8) . . . . ? C2 O3 C4 O4 -160.62(8) . . . . ? C2 O3 C4 C5 22.66(11) . . . . ? O4 C4 C5 C6 3.72(14) . . . . ? O3 C4 C5 C6 -179.80(8) . . . . ? O4 C4 C5 C14 -171.20(9) . . . . ? O3 C4 C5 C14 5.29(12) . . . . ? C14 C5 C6 C7 -0.72(14) . . . . ? C4 C5 C6 C7 -175.64(8) . . . . ? C5 C6 C7 C8 -179.56(9) . . . . ? C5 C6 C7 C12 0.15(13) . . . . ? C6 C7 C8 C9 178.73(9) . . . . ? C12 C7 C8 C9 -0.98(14) . . . . ? C7 C8 C9 C10 1.39(14) . . . . ? C8 C9 C10 C11 -1.02(15) . . . . ? C9 C10 C11 C12 0.22(15) . . . . ? C10 C11 C12 C13 -179.57(9) . . . . ? C10 C11 C12 C7 0.18(14) . . . . ? C6 C7 C12 C13 0.22(13) . . . . ? C8 C7 C12 C13 179.94(9) . . . . ? C6 C7 C12 C11 -179.53(9) . . . . ? C8 C7 C12 C11 0.18(13) . . . . ? C11 C12 C13 C14 179.74(9) . . . . ? C7 C12 C13 C14 -0.01(14) . . . . ? C12 C13 C14 O1 176.41(8) . . . . ? C12 C13 C14 C5 -0.58(14) . . . . ? C2 O1 C14 C13 152.38(9) . . . . ? C2 O1 C14 C5 -30.55(11) . . . . ? C6 C5 C14 C13 0.95(14) . . . . ? C4 C5 C14 C13 175.89(9) . . . . ? C6 C5 C14 O1 -176.06(8) . . . . ? C4 C5 C14 O1 -1.12(13) . . . . ? 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 C2 H2 O4 1.00 2.47 3.0894(12) 119.5 1_556 C2 H2 O4 1.00 2.51 3.3547(12) 141.4 4_566 C10 H10 O3 0.95 2.53 3.4562(13) 165.9 1_455 C15 H151 O4 0.98 2.73 3.3024(13) 117.9 1_556 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.463 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.061