Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'I. Csoregh' _publ_contact_author_address ; Structural Chemistry Stockholm University Stockholm SWEDEN ; _publ_contact_author_email ICS@STRUC.SU.SE _publ_section_title ; A new organic zeolite created by molecular aggregation of 1,1-bis(3,4-dihydroxyphenyl)cyclohexane in the solid state ; loop_ _publ_author_name 'I. Csoregh' 'Masako Kato' 'Hiroyuki Ohta' 'Yasuhisa Shigetomi' 'Itsuki Takeshita' 'Fumio Toda' ; S.Toyota ; 'Kazuhiro Yoshizawa' data_1c _database_code_depnum_ccdc_archive 'CCDC 642537' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 O2' _chemical_formula_sum 'C20 H24 O2' _chemical_formula_weight 296.39 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 2(1)/ a' _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.5009(8) _cell_length_b 9.8934(5) _cell_length_c 14.9322(11) _cell_angle_alpha 90.00 _cell_angle_beta 112.1680(10) _cell_angle_gamma 90.00 _cell_volume 1573.44(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9572 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8766 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2594 _reflns_number_gt 2412 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Rigaku/MSC and Rogaku Corporation (2005). Crystal Structure 3.7.0. Single Crystal Structure Analysis Software. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381--5209. Rigaku, 3-9-12 Akishima, Tokyo 196-8666, Japan. ; _computing_cell_refinement ; Rigaku/MSC and Rogaku Corporation (2005). Crystal Structure 3.7.0. Single Crystal Structure Analysis Software. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381--5209. Rigaku, 3-9-12 Akishima, Tokyo 196-8666, Japan. ; _computing_data_reduction ; Watkin, D. J., Prout, C. K. Carruthers, J. R. & Betteridge, P. W. (1996). CRYSTALS, Issue 10, Chemical Crystallography Laboratory, Oxford, UK. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/XP (Sheldrick, 1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.5900P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2594 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.51027(11) -0.27923(11) 0.71684(9) 0.0310(3) Uani 1 1 d . . . H1O H 0.5542 -0.2479 0.6780 0.068(7) Uiso 1 1 d R . . O2 O -0.13761(11) 0.25050(13) 0.41174(8) 0.0345(3) Uani 1 1 d . . . H2O H -0.1957 0.1854 0.3982 0.078(9) Uiso 1 1 d R . . C13 C 0.23174(14) 0.15661(15) 0.79093(10) 0.0190(3) Uani 1 1 d . . . C14 C 0.16751(14) 0.11902(16) 0.86191(11) 0.0229(3) Uani 1 1 d . . . H14A H 0.1061 0.1905 0.8596 0.028(5) Uiso 1 1 calc R . . H14B H 0.1204 0.0336 0.8400 0.026(4) Uiso 1 1 calc R . . C15 C 0.25890(16) 0.10182(17) 0.96655(11) 0.0280(4) Uani 1 1 d . . . H15A H 0.2112 0.0811 1.0079 0.030(5) Uiso 1 1 calc R . . H15B H 0.3156 0.0247 0.9707 0.037(5) Uiso 1 1 calc R . . C16 C 0.33640(17) 0.22880(19) 1.00344(12) 0.0326(4) Uani 1 1 d . . . H16A H 0.3987 0.2131 1.0696 0.034(5) Uiso 1 1 calc R . . H16B H 0.2809 0.3039 1.0061 0.044(6) Uiso 1 1 calc R . . C17 C 0.40396(16) 0.26689(18) 0.93672(12) 0.0299(4) Uani 1 1 d . . . H17A H 0.4655 0.1955 0.9393 0.039(5) Uiso 1 1 calc R . . H17B H 0.4506 0.3523 0.9595 0.038(5) Uiso 1 1 calc R . . C18 C 0.31205(15) 0.28429(16) 0.83253(11) 0.0236(3) Uani 1 1 d . . . H18A H 0.3597 0.3072 0.7915 0.022(4) Uiso 1 1 calc R . . H18B H 0.2554 0.3610 0.8295 0.032(5) Uiso 1 1 calc R . . C4 C 0.31308(13) 0.04080(15) 0.77686(10) 0.0194(3) Uani 1 1 d . . . C3 C 0.29747(14) -0.09332(15) 0.79909(10) 0.0197(3) Uani 1 1 d . . . H3 H 0.2398 -0.1122 0.8292 0.028(5) Uiso 1 1 calc R . . C2 C 0.36212(15) -0.20060(15) 0.77928(11) 0.0212(3) Uani 1 1 d . . . C1 C 0.44730(15) -0.17180(15) 0.73570(11) 0.0221(3) Uani 1 1 d . . . C6 C 0.46640(15) -0.03949(16) 0.71368(11) 0.0236(3) Uani 1 1 d . . . H6 H 0.5255 -0.0206 0.6849 0.029(5) Uiso 1 1 calc R . . C5 C 0.39982(14) 0.06517(16) 0.73337(11) 0.0226(3) Uani 1 1 d . . . H5 H 0.4131 0.1551 0.7171 0.030(5) Uiso 1 1 calc R . . C19 C 0.34138(17) -0.34431(16) 0.80288(12) 0.0288(4) Uani 1 1 d . . . H19A H 0.2737 -0.3471 0.8276 0.048(6) Uiso 1 1 calc R . . H19B H 0.4187 -0.3797 0.8521 0.050(6) Uiso 1 1 calc R . . H19C H 0.3182 -0.3997 0.7443 0.056(6) Uiso 1 1 calc R . . C10 C 0.12997(14) 0.18541(15) 0.69041(10) 0.0199(3) Uani 1 1 d . . . C9 C 0.02690(14) 0.09857(15) 0.65114(11) 0.0213(3) Uani 1 1 d . . . H9 H 0.0194 0.0246 0.6892 0.025(4) Uiso 1 1 calc R . . C8 C -0.06502(14) 0.11532(16) 0.55923(11) 0.0231(3) Uani 1 1 d . . . C7 C -0.05236(15) 0.22501(17) 0.50522(11) 0.0249(3) Uani 1 1 d . . . C12 C 0.04707(15) 0.31316(17) 0.54125(11) 0.0266(4) Uani 1 1 d . . . H12 H 0.0535 0.3878 0.5033 0.032(5) Uiso 1 1 calc R . . C11 C 0.13813(15) 0.29313(16) 0.63306(11) 0.0238(3) Uani 1 1 d . . . H11 H 0.2070 0.3539 0.6570 0.038(5) Uiso 1 1 calc R . . C20 C -0.17251(15) 0.01739(19) 0.51887(12) 0.0307(4) Uani 1 1 d . . . H20A H -0.2521 0.0671 0.4968 0.063(7) Uiso 1 1 calc R . . H20B H -0.1705 -0.0471 0.5693 0.052(6) Uiso 1 1 calc R . . H20C H -0.1649 -0.0316 0.4643 0.052(6) 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 0.0347(7) 0.0253(6) 0.0374(7) 0.0009(5) 0.0186(6) 0.0084(5) O2 0.0276(6) 0.0490(8) 0.0210(6) 0.0048(5) 0.0027(5) 0.0017(6) C13 0.0191(8) 0.0183(7) 0.0187(7) -0.0011(6) 0.0061(6) -0.0006(6) C14 0.0228(8) 0.0252(8) 0.0218(7) -0.0027(6) 0.0099(6) 0.0004(7) C15 0.0317(9) 0.0329(9) 0.0210(8) -0.0001(7) 0.0118(7) 0.0006(8) C16 0.0369(10) 0.0374(10) 0.0194(8) -0.0058(7) 0.0059(7) -0.0030(8) C17 0.0300(9) 0.0294(9) 0.0254(8) -0.0050(7) 0.0048(7) -0.0066(8) C18 0.0251(8) 0.0211(8) 0.0236(8) -0.0031(6) 0.0081(7) -0.0012(7) C4 0.0181(7) 0.0205(8) 0.0174(7) -0.0013(6) 0.0042(6) -0.0004(6) C3 0.0196(8) 0.0213(8) 0.0181(7) 0.0007(6) 0.0069(6) -0.0013(6) C2 0.0223(8) 0.0204(8) 0.0180(7) 0.0001(6) 0.0042(6) 0.0000(6) C1 0.0210(8) 0.0234(8) 0.0200(7) -0.0017(6) 0.0056(6) 0.0045(6) C6 0.0219(8) 0.0270(8) 0.0242(8) 0.0017(7) 0.0113(7) 0.0000(7) C5 0.0237(8) 0.0204(8) 0.0243(8) 0.0014(6) 0.0097(7) -0.0010(6) C19 0.0338(10) 0.0211(8) 0.0316(9) 0.0024(7) 0.0124(8) 0.0002(7) C10 0.0198(8) 0.0198(8) 0.0208(7) -0.0024(6) 0.0086(6) 0.0021(6) C9 0.0233(8) 0.0197(8) 0.0222(7) -0.0010(6) 0.0100(6) 0.0007(6) C8 0.0201(8) 0.0271(8) 0.0232(8) -0.0050(6) 0.0096(6) 0.0015(7) C7 0.0209(8) 0.0336(9) 0.0188(7) 0.0006(7) 0.0059(6) 0.0061(7) C12 0.0285(9) 0.0264(8) 0.0250(8) 0.0048(7) 0.0102(7) 0.0032(7) C11 0.0224(8) 0.0238(8) 0.0250(8) -0.0005(6) 0.0087(7) -0.0014(7) C20 0.0240(9) 0.0401(10) 0.0270(9) -0.0075(7) 0.0085(7) -0.0042(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3739(18) . ? O1 H1O 0.9527 . ? O2 C7 1.3931(18) . ? O2 H2O 0.8944 . ? C13 C4 1.543(2) . ? C13 C10 1.542(2) . ? C13 C14 1.549(2) . ? C13 C18 1.550(2) . ? C14 C15 1.528(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.518(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.524(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.525(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C4 C3 1.396(2) . ? C4 C5 1.401(2) . ? C3 C2 1.390(2) . ? C3 H3 0.9500 . ? C2 C1 1.395(2) . ? C2 C19 1.505(2) . ? C1 C6 1.387(2) . ? C6 C5 1.384(2) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C10 C11 1.392(2) . ? C10 C9 1.401(2) . ? C9 C8 1.390(2) . ? C9 H9 0.9500 . ? C8 C7 1.392(2) . ? C8 C20 1.506(2) . ? C7 C12 1.376(2) . ? C12 C11 1.390(2) . ? C12 H12 0.9500 . ? C11 H11 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C1 O1 H1O 108.3 . . ? C7 O2 H2O 106.2 . . ? C4 C13 C10 106.33(11) . . ? C4 C13 C14 112.66(12) . . ? C10 C13 C14 109.13(12) . . ? C4 C13 C18 111.07(12) . . ? C10 C13 C18 110.99(12) . . ? C14 C13 C18 106.71(12) . . ? C15 C14 C13 113.88(13) . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 111.21(14) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 109.98(13) . . ? C15 C16 H16A 109.7 . . ? C17 C16 H16A 109.7 . . ? C15 C16 H16B 109.7 . . ? C17 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? C16 C17 C18 111.51(14) . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C17 C18 C13 113.31(13) . . ? C17 C18 H18A 108.9 . . ? C13 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C13 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C3 C4 C5 116.85(14) . . ? C3 C4 C13 122.32(13) . . ? C5 C4 C13 120.64(13) . . ? C2 C3 C4 123.24(14) . . ? C2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C3 C2 C1 118.00(14) . . ? C3 C2 C19 121.77(14) . . ? C1 C2 C19 120.23(14) . . ? O1 C1 C6 122.59(14) . . ? O1 C1 C2 117.06(14) . . ? C6 C1 C2 120.35(14) . . ? C5 C6 C1 120.39(14) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C6 C5 C4 121.16(14) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C2 C19 H19A 109.5 . . ? C2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C11 C10 C9 117.04(14) . . ? C11 C10 C13 122.52(13) . . ? C9 C10 C13 120.37(13) . . ? C8 C9 C10 123.24(15) . . ? C8 C9 H9 118.4 . . ? C10 C9 H9 118.4 . . ? C9 C8 C7 117.25(14) . . ? C9 C8 C20 121.46(15) . . ? C7 C8 C20 121.28(14) . . ? C12 C7 O2 116.36(15) . . ? C12 C7 C8 121.38(14) . . ? O2 C7 C8 122.26(15) . . ? C7 C12 C11 120.07(15) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C10 C11 C12 121.01(15) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C8 C20 H20A 109.5 . . ? C8 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C8 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C4 C13 C14 C15 67.87(17) . . . . ? C10 C13 C14 C15 -174.27(13) . . . . ? C18 C13 C14 C15 -54.28(17) . . . . ? C13 C14 C15 C16 57.09(18) . . . . ? C14 C15 C16 C17 -55.53(19) . . . . ? C15 C16 C17 C18 56.08(19) . . . . ? C16 C17 C18 C13 -57.56(18) . . . . ? C4 C13 C18 C17 -68.82(16) . . . . ? C10 C13 C18 C17 173.12(13) . . . . ? C14 C13 C18 C17 54.33(16) . . . . ? C10 C13 C4 C3 -99.83(15) . . . . ? C14 C13 C4 C3 19.67(19) . . . . ? C18 C13 C4 C3 139.32(14) . . . . ? C10 C13 C4 C5 74.94(16) . . . . ? C14 C13 C4 C5 -165.57(13) . . . . ? C18 C13 C4 C5 -45.91(18) . . . . ? C5 C4 C3 C2 -0.7(2) . . . . ? C13 C4 C3 C2 174.29(13) . . . . ? C4 C3 C2 C1 0.5(2) . . . . ? C4 C3 C2 C19 -179.02(14) . . . . ? C3 C2 C1 O1 179.93(13) . . . . ? C19 C2 C1 O1 -0.5(2) . . . . ? C3 C2 C1 C6 0.3(2) . . . . ? C19 C2 C1 C6 179.86(14) . . . . ? O1 C1 C6 C5 179.45(14) . . . . ? C2 C1 C6 C5 -1.0(2) . . . . ? C1 C6 C5 C4 0.8(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C13 C4 C5 C6 -175.04(13) . . . . ? C4 C13 C10 C11 -100.58(16) . . . . ? C14 C13 C10 C11 137.65(15) . . . . ? C18 C13 C10 C11 20.33(19) . . . . ? C4 C13 C10 C9 76.47(16) . . . . ? C14 C13 C10 C9 -45.30(18) . . . . ? C18 C13 C10 C9 -162.63(13) . . . . ? C11 C10 C9 C8 0.2(2) . . . . ? C13 C10 C9 C8 -177.00(14) . . . . ? C10 C9 C8 C7 -0.4(2) . . . . ? C10 C9 C8 C20 178.39(14) . . . . ? C9 C8 C7 C12 0.1(2) . . . . ? C20 C8 C7 C12 -178.75(15) . . . . ? C9 C8 C7 O2 178.94(14) . . . . ? C20 C8 C7 O2 0.1(2) . . . . ? O2 C7 C12 C11 -178.43(14) . . . . ? C8 C7 C12 C11 0.5(2) . . . . ? C9 C10 C11 C12 0.4(2) . . . . ? C13 C10 C11 C12 177.53(14) . . . . ? C7 C12 C11 C10 -0.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.718 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.718 _refine_diff_density_max 0.231 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.040 # Attachment 'BCCB.CIF' data_bccb _database_code_depnum_ccdc_archive 'CCDC 642538' _audit_creation_method ; from SHELXL-97 and manual editing ; _chemical_name_systematic ; 1,1-bis(cathecolyl)cyclohexane.benzene (1:1) complex ; _chemical_name_common '1,1-bis(cathecolyl)cyclohexane.benzene (1:1) complex' _chemical_melting_point ? _chemical_formula_moiety '(C18 H20 O4),(C6 H6)' _chemical_formula_sum 'C24 H26 O4' _chemical_formula_weight 378.45 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 2(1)/a' _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.146(2) _cell_length_b 17.455(2) _cell_length_c 12.088(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.90(2) _cell_angle_gamma 90.00 _cell_volume 1999.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'area detector scans (phi)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5000 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14887 _diffrn_reflns_av_R_equivalents 0.1034 _diffrn_reflns_av_sigmaI/netI 0.0789 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.94 _reflns_number_total 3837 _reflns_number_gt 2294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE & CIE GmbH 1997 (Publications 4805-014)' _computing_cell_refinement 'STOE & CIE GmbH 1997 (Publications 4805-014)' _computing_data_reduction 'STOE & CIE GmbH 1997 (Publications 4805-014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/XP (Sheldrick, 1990)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 2003) ; _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^)+(0.0855P)^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 refu _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3837 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _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 1.08313(14) 0.27576(8) 1.16238(11) 0.0461(4) Uani 1 1 d . . . H1O1 H 1.1757 0.2890 1.1612 0.071(7) Uiso 1 1 d R . . O2 O 0.85579(14) 0.19453(8) 1.17080(11) 0.0473(4) Uani 1 1 d . . . H1O2 H 0.9323 0.2115 1.2461 0.098(10) Uiso 1 1 d R . . C1 C 1.01558(19) 0.22538(11) 1.07057(15) 0.0368(4) Uani 1 1 d . . . C2 C 0.90201(18) 0.18458(11) 1.07728(15) 0.0354(4) Uani 1 1 d . . . C3 C 0.83212(18) 0.13261(11) 0.98917(15) 0.0356(4) Uani 1 1 d . . . H3 H 0.7570 0.1048 0.9956 0.043(5) Uiso 1 1 calc R . . C4 C 0.87153(18) 0.12109(10) 0.89159(14) 0.0338(4) Uani 1 1 d . . . C5 C 0.9842(2) 0.16427(12) 0.88579(17) 0.0464(5) Uani 1 1 d . . . H5 H 1.0120 0.1586 0.8208 0.064(7) Uiso 1 1 calc R . . C6 C 1.0559(2) 0.21531(13) 0.97407(17) 0.0474(5) Uani 1 1 d . . . H6 H 1.1316 0.2430 0.9684 0.064(7) Uiso 1 1 calc R . . O7 O 0.48906(14) 0.26105(8) 0.40486(11) 0.0445(4) Uani 1 1 d . . . H1O7 H 0.4124 0.2845 0.4195 0.086(9) Uiso 1 1 d R . . O8 O 0.72942(13) 0.19097(8) 0.40625(11) 0.0438(4) Uani 1 1 d . . . H1O8 H 0.6564 0.2022 0.3314 0.079(8) Uiso 1 1 d R . . C7 C 0.55742(18) 0.21241(10) 0.49805(15) 0.0350(4) Uani 1 1 d . . . C8 C 0.68012(18) 0.17776(11) 0.49770(15) 0.0338(4) Uani 1 1 d . . . C9 C 0.75602(18) 0.12983(10) 0.58966(15) 0.0349(4) Uani 1 1 d . . . H9 H 0.8388 0.1074 0.5887 0.040(5) Uiso 1 1 calc R . . C10 C 0.71071(17) 0.11452(10) 0.68380(15) 0.0330(4) Uani 1 1 d . . . C11 C 0.5869(2) 0.14958(12) 0.68125(16) 0.0423(5) Uani 1 1 d . . . H11 H 0.5538 0.1404 0.7425 0.055(6) Uiso 1 1 calc R . . C12 C 0.5114(2) 0.19784(12) 0.58990(16) 0.0436(5) Uani 1 1 d . . . H12 H 0.4289 0.2206 0.5907 0.054(6) Uiso 1 1 calc R . . C13 C 0.79558(18) 0.06439(11) 0.79083(15) 0.0358(4) Uani 1 1 d . . . C14 C 0.6965(2) 0.01068(11) 0.82602(17) 0.0451(5) Uani 1 1 d . . . H14A H 0.7495 -0.0140 0.9006 0.051(6) Uiso 1 1 calc R . . H14B H 0.6224 0.0409 0.8379 0.053(6) Uiso 1 1 calc R . . C15 C 0.6292(3) -0.05091(13) 0.7327(2) 0.0581(6) Uani 1 1 d . . . H15A H 0.5693 -0.0835 0.7596 0.061(7) Uiso 1 1 calc R . . H15B H 0.5707 -0.0267 0.6594 0.067(7) Uiso 1 1 calc R . . C16 C 0.7413(3) -0.09930(13) 0.7102(2) 0.0685(7) Uani 1 1 d . . . H16A H 0.7926 -0.1282 0.7810 0.084(9) Uiso 1 1 calc R . . H16B H 0.6965 -0.1355 0.6470 0.084(8) Uiso 1 1 calc R . . C17 C 0.8434(3) -0.04976(13) 0.6763(2) 0.0587(6) Uani 1 1 d . . . H17A H 0.7946 -0.0269 0.5994 0.062(7) Uiso 1 1 calc R . . H17B H 0.9189 -0.0815 0.6700 0.063(7) Uiso 1 1 calc R . . C18 C 0.9065(2) 0.01357(11) 0.76685(16) 0.0445(5) Uani 1 1 d . . . H18A H 0.9661 0.0457 0.7388 0.040(5) Uiso 1 1 calc R . . H18B H 0.9658 -0.0096 0.8408 0.048(6) Uiso 1 1 calc R . . C1B C 0.2633(7) 0.1473(2) 0.7505(9) 0.084(2) Uani 0.894(16) 1 d P . . H1B H 0.2599 0.2006 0.7476 0.151(18) Uiso 0.894(16) 1 d PR . . C2B C 0.2095(4) 0.1041(4) 0.6531(6) 0.0874(17) Uani 0.894(16) 1 d P . . H2B H 0.1671 0.1290 0.5810 0.136(16) Uiso 0.894(16) 1 d PR . . C3B C 0.2189(6) 0.0262(4) 0.6616(4) 0.0983(19) Uani 0.894(16) 1 d P . . H3B H 0.1799 -0.0021 0.5924 0.138(17) Uiso 0.894(16) 1 d PR . . C4B C 0.2777(7) -0.0068(3) 0.7666(7) 0.098(3) Uani 0.894(16) 1 d P . . H4B H 0.2811 -0.0601 0.7695 0.090(11) Uiso 0.894(16) 1 d PR . . C5B C 0.3314(6) 0.0348(6) 0.8664(5) 0.098(2) Uani 0.894(16) 1 d P . . H5B H 0.3738 0.0099 0.9385 0.118(14) Uiso 0.894(16) 1 d PR . . C6B C 0.3255(7) 0.1133(6) 0.8601(7) 0.096(2) Uani 0.894(16) 1 d P . . H6B H 0.3645 0.1416 0.9293 0.132(16) Uiso 0.894(16) 1 d PR . . C1'B C 0.220(2) 0.1309(17) 0.707(4) 0.040(9) Uiso 0.106(16) 1 d PG . . C2'B C 0.205(3) 0.056(2) 0.665(2) 0.054(11) Uiso 0.106(16) 1 d PG . . C3'B C 0.269(4) -0.0038(14) 0.741(4) 0.064(16) Uiso 0.106(16) 1 d PG . . C4'B C 0.349(4) 0.0112(16) 0.859(3) 0.072(15) Uiso 0.106(16) 1 d PG . . C5'B C 0.364(4) 0.086(2) 0.901(2) 0.089(16) Uiso 0.106(16) 1 d PG . . C6'B C 0.300(3) 0.1459(12) 0.825(4) 0.048(9) Uiso 0.106(16) 1 d PG . . 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 0.0459(8) 0.0545(9) 0.0390(7) -0.0118(6) 0.0164(6) -0.0101(6) O2 0.0427(8) 0.0686(10) 0.0354(7) -0.0117(6) 0.0200(6) -0.0069(7) C1 0.0359(10) 0.0417(10) 0.0299(9) -0.0007(7) 0.0082(8) 0.0006(8) C2 0.0336(9) 0.0446(11) 0.0288(9) 0.0013(8) 0.0120(7) 0.0043(8) C3 0.0322(9) 0.0423(11) 0.0328(9) 0.0012(8) 0.0122(8) -0.0022(8) C4 0.0325(9) 0.0368(10) 0.0312(9) 0.0035(7) 0.0102(7) 0.0021(8) C5 0.0455(11) 0.0625(13) 0.0357(10) -0.0075(9) 0.0201(9) -0.0096(10) C6 0.0451(11) 0.0602(13) 0.0407(11) -0.0063(9) 0.0199(9) -0.0168(10) O7 0.0438(8) 0.0540(8) 0.0367(7) 0.0125(6) 0.0156(6) 0.0124(7) O8 0.0383(7) 0.0623(9) 0.0339(7) 0.0090(6) 0.0166(6) 0.0018(6) C7 0.0347(9) 0.0391(10) 0.0288(9) 0.0018(7) 0.0082(7) 0.0005(8) C8 0.0331(9) 0.0397(10) 0.0304(9) -0.0023(7) 0.0134(7) -0.0050(8) C9 0.0315(9) 0.0391(10) 0.0345(9) -0.0020(8) 0.0121(8) 0.0017(8) C10 0.0337(9) 0.0343(9) 0.0304(9) -0.0012(7) 0.0106(7) -0.0012(7) C11 0.0414(10) 0.0546(12) 0.0359(10) 0.0080(9) 0.0198(8) 0.0077(9) C12 0.0393(10) 0.0566(12) 0.0391(10) 0.0070(9) 0.0188(9) 0.0145(9) C13 0.0371(9) 0.0385(10) 0.0305(9) 0.0000(7) 0.0105(7) 0.0003(8) C14 0.0490(11) 0.0416(11) 0.0420(10) 0.0057(9) 0.0129(9) -0.0047(9) C15 0.0645(14) 0.0441(12) 0.0588(14) -0.0004(10) 0.0133(12) -0.0149(11) C16 0.0872(17) 0.0397(12) 0.0662(15) -0.0058(12) 0.0123(14) -0.0001(12) C17 0.0722(15) 0.0441(12) 0.0554(13) -0.0079(10) 0.0175(12) 0.0163(12) C18 0.0493(11) 0.0418(11) 0.0392(10) 0.0015(9) 0.0116(9) 0.0100(9) C1B 0.074(3) 0.062(2) 0.133(8) -0.005(3) 0.058(4) -0.002(2) C2B 0.093(2) 0.097(4) 0.082(4) 0.018(3) 0.043(2) 0.000(2) C3B 0.142(4) 0.082(3) 0.101(4) -0.016(3) 0.081(4) -0.014(3) C4B 0.125(6) 0.065(3) 0.137(6) 0.021(3) 0.086(5) 0.014(2) C5B 0.075(3) 0.139(6) 0.091(3) 0.046(4) 0.043(3) 0.010(4) C6B 0.073(3) 0.134(5) 0.093(4) -0.031(5) 0.046(3) -0.023(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 C1 1.390(2) . ? O1 H1O1 0.9722 . ? O2 C2 1.381(2) . ? O2 H1O2 1.0071 . ? C1 C6 1.378(3) . ? C1 C2 1.381(3) . ? C2 C3 1.386(3) . ? C3 C4 1.389(2) . ? C3 H3 0.9300 . ? C4 C5 1.392(3) . ? C4 C13 1.545(2) . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? O7 C7 1.383(2) . ? O7 H1O7 0.9499 . ? O8 C8 1.386(2) . ? O8 H1O8 0.9625 . ? C7 C12 1.373(3) . ? C7 C8 1.385(3) . ? C8 C9 1.385(3) . ? C9 C10 1.397(2) . ? C9 H9 0.9300 . ? C10 C11 1.388(3) . ? C10 C13 1.545(2) . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.539(3) . ? C13 C14 1.542(3) . ? C14 C15 1.531(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.517(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.514(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.526(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C1B C6B 1.383(8) . ? C1B C2B 1.339(7) . ? C1B H1B 0.9300 . ? C2B C3B 1.365(7) . ? C2B H2B 0.9300 . ? C3B C4B 1.327(7) . ? C3B H3B 0.9300 . ? C4B C5B 1.346(7) . ? C4B H4B 0.9300 . ? C5B C6B 1.372(9) . ? C5B H5B 0.9300 . ? C6B H6B 0.9300 . ? C1'B C2'B 1.3900 . ? C1'B C6'B 1.3900 . ? C2'B C3'B 1.3900 . ? C3'B C4'B 1.3900 . ? C4'B C5'B 1.3900 . ? C5'B C6'B 1.3900 . ? 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 C1 O1 H1O1 110.0 . . ? C2 O2 H1O2 113.5 . . ? C6 C1 C2 119.33(17) . . ? C6 C1 O1 123.07(17) . . ? C2 C1 O1 117.60(16) . . ? O2 C2 C1 121.16(16) . . ? O2 C2 C3 118.77(17) . . ? C1 C2 C3 120.07(17) . . ? C2 C3 C4 121.60(17) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 117.07(17) . . ? C3 C4 C13 123.27(16) . . ? C5 C4 C13 119.66(16) . . ? C6 C5 C4 121.74(18) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C1 C6 C5 120.16(19) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C7 O7 H1O7 108.6 . . ? C8 O8 H1O8 114.1 . . ? C12 C7 O7 123.78(17) . . ? C12 C7 C8 119.12(16) . . ? O7 C7 C8 117.09(16) . . ? C9 C8 O8 119.03(16) . . ? C9 C8 C7 120.28(16) . . ? O8 C8 C7 120.68(16) . . ? C8 C9 C10 121.27(17) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 117.13(16) . . ? C11 C10 C13 119.87(16) . . ? C9 C10 C13 122.93(16) . . ? C12 C11 C10 121.67(18) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C7 C12 C11 120.52(18) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C18 C13 C4 108.97(14) . . ? C18 C13 C14 107.11(17) . . ? C4 C13 C14 111.29(15) . . ? C18 C13 C10 113.28(15) . . ? C4 C13 C10 105.64(14) . . ? C14 C13 C10 110.61(14) . . ? C15 C14 C13 112.76(17) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 110.94(19) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C15 111.07(19) . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 111.8(2) . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C13 113.88(17) . . ? C17 C18 H18A 108.8 . . ? C13 C18 H18A 108.8 . . ? C17 C18 H18B 108.8 . . ? C13 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C6B C1B C2B 120.3(4) . . ? C6B C1B H1B 117.6 . . ? C2B C1B H1B 122.1 . . ? C3B C2B C1B 119.9(4) . . ? C3B C2B H2B 122.2 . . ? C1B C2B H2B 117.9 . . ? C2B C3B C4B 120.1(4) . . ? C2B C3B H3B 117.8 . . ? C4B C3B H3B 122.1 . . ? C3B C4B C5B 121.5(5) . . ? C3B C4B H4B 117.9 . . ? C5B C4B H4B 120.6 . . ? C4B C5B C6B 119.6(5) . . ? C4B C5B H5B 119.4 . . ? C6B C5B H5B 120.9 . . ? C1B C6B C5B 118.5(4) . . ? C1B C6B H6B 122.4 . . ? C5B C6B H6B 119.1 . . ? C2'B C1'B C6'B 120.0 . . ? C1'B C2'B C3'B 120.0 . . ? C4'B C3'B C2'B 120.0 . . ? C6'B C5'B C4'B 120.0 . . ? C5'B C6'B C1'B 120.0 . . ? 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 C6 C1 C2 O2 -178.21(18) . . . . ? O1 C1 C2 O2 1.1(3) . . . . ? C6 C1 C2 C3 1.7(3) . . . . ? O1 C1 C2 C3 -178.95(16) . . . . ? O2 C2 C3 C4 178.67(16) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C2 C3 C4 C13 -179.35(16) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C13 C4 C5 C6 -179.57(18) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? O1 C1 C6 C5 -179.99(19) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? C12 C7 C8 C9 -0.8(3) . . . . ? O7 C7 C8 C9 178.42(16) . . . . ? C12 C7 C8 O8 179.81(17) . . . . ? O7 C7 C8 O8 -1.0(2) . . . . ? O8 C8 C9 C10 -179.86(15) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C8 C9 C10 C13 -177.15(16) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C13 C10 C11 C12 176.82(18) . . . . ? O7 C7 C12 C11 -178.78(18) . . . . ? C8 C7 C12 C11 0.4(3) . . . . ? C10 C11 C12 C7 0.1(3) . . . . ? C3 C4 C13 C18 -130.78(18) . . . . ? C5 C4 C13 C18 50.1(2) . . . . ? C3 C4 C13 C14 -12.9(2) . . . . ? C5 C4 C13 C14 168.00(17) . . . . ? C3 C4 C13 C10 107.21(18) . . . . ? C5 C4 C13 C10 -71.9(2) . . . . ? C11 C10 C13 C18 165.10(17) . . . . ? C9 C10 C13 C18 -18.0(2) . . . . ? C11 C10 C13 C4 -75.7(2) . . . . ? C9 C10 C13 C4 101.17(19) . . . . ? C11 C10 C13 C14 44.8(2) . . . . ? C9 C10 C13 C14 -138.30(18) . . . . ? C18 C13 C14 C15 -55.9(2) . . . . ? C4 C13 C14 C15 -174.96(16) . . . . ? C10 C13 C14 C15 67.9(2) . . . . ? C13 C14 C15 C16 58.2(2) . . . . ? C14 C15 C16 C17 -55.1(3) . . . . ? C15 C16 C17 C18 53.4(2) . . . . ? C16 C17 C18 C13 -54.8(2) . . . . ? C4 C13 C18 C17 174.84(16) . . . . ? C14 C13 C18 C17 54.3(2) . . . . ? C10 C13 C18 C17 -67.9(2) . . . . ? C1B C2B C3B C4B 1.8(6) . . . . ? C2B C3B C4B C5B -1.1(7) . . . . ? C3B C4B C5B C6B 0.0(7) . . . . ? C2B C1B C6B C5B 0.4(6) . . . . ? C4B C5B C6B C1B 0.3(6) . . . . ? C1'B C2'B C3'B C4'B 0.0 . . . . ? C2'B C3'B C4'B C5'B 0.0 . . . . ? C3'B C4'B C5'B C6'B 0.0 . . . . ? C4'B C5'B C6'B C1'B 0.0 . . . . ? C2'B C1'B C6'B C5'B 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.261 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.048 # Attachment 'BCCX.CIF' data_bccx _database_code_depnum_ccdc_archive 'CCDC 642539' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C18 H20 O4),(C8 H10)' _chemical_formula_sum 'C26 H30 O4' _chemical_formula_weight 406.50 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.263(4) _cell_length_b 12.628(4) _cell_length_c 17.701(6) _cell_angle_alpha 93.276(4) _cell_angle_beta 96.005(3) _cell_angle_gamma 107.958(5) _cell_volume 2160.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9489 _exptl_absorpt_correction_T_max 0.9680 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16992 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9375 _reflns_number_gt 7081 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Rigaku/MSC and Rigaku Corporation (2005). Crystal Structure 3.7.0. Single Crystal Structure Analysis Software. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381-5209. Rigaku. 3-9-12 Akishima, Tokyo 196-8666, Japan. ; _computing_cell_refinement ; Rigaku/MSC and Rigaku Corporation (2005). Crystal Structure 3.7.0. Single Crystal Structure Analysis Software. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381-5209. Rigaku. 3-9-12 Akishima, Tokyo 196-8666, Japan. ; _computing_data_reduction ; Watkin, D. J., Prout, C. K., Carruthers, J. R. & Betteridge, P. W. (1996). CRYSTALS Issue 10, Chemical Crystallography Laboratory, Oxford, UK. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/XP (Sheldrick, 1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.1350P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9375 _refine_ls_number_parameters 605 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1392 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.37795(8) 0.31709(7) 1.20050(5) 0.0253(2) Uani 1 1 d . . . H1O H 0.4715 0.3461 1.2069 0.050(5) Uiso 1 1 d R . . O2 O 0.09943(8) 0.24430(8) 1.15915(5) 0.0274(2) Uani 1 1 d . . . H2O H 0.1455 0.2468 1.2061 0.059(5) Uiso 1 1 d R . . O7 O 0.14130(9) 0.71646(7) 0.81839(5) 0.0262(2) Uani 1 1 d . . . H7O H 0.0780 0.7354 0.8369 0.056(5) Uiso 1 1 d R . . O8 O 0.34099(8) 0.63529(7) 0.77183(5) 0.0282(2) Uani 1 1 d . . . H8O H 0.3230 0.6985 0.7570 0.059(5) Uiso 1 1 d R . . O19 O -0.36689(9) 0.16249(7) 0.29163(5) 0.0260(2) Uani 1 1 d . . . H19O H -0.4536 0.1405 0.2851 0.051(5) Uiso 1 1 calc R . . O20 O -0.08866(8) 0.24391(7) 0.33596(5) 0.0255(2) Uani 1 1 d . . . H20O H -0.1387 0.2435 0.2882 0.066(6) Uiso 1 1 d R . . O25 O -0.15835(9) -0.20961(7) 0.68546(5) 0.0254(2) Uani 1 1 d . . . H25O H -0.0790 -0.2250 0.6726 0.074(6) Uiso 1 1 d R . . O26 O -0.34805(8) -0.11660(7) 0.73523(5) 0.0252(2) Uani 1 1 d . . . H26O H -0.3333 -0.1873 0.7474 0.069(6) Uiso 1 1 d R . . C1 C 0.32923(12) 0.30898(9) 1.12395(6) 0.0204(2) Uani 1 1 d . . . C2 C 0.18721(12) 0.27118(9) 1.10384(7) 0.0202(2) Uani 1 1 d . . . C3 C 0.13002(12) 0.26036(10) 1.02823(7) 0.0212(3) Uani 1 1 d . . . H3 H 0.0324 0.2340 1.0157 0.022(3) Uiso 1 1 calc R . . C4 C 0.21346(12) 0.28752(9) 0.97002(6) 0.0203(2) Uani 1 1 d . . . C5 C 0.35587(12) 0.32669(11) 0.99144(7) 0.0258(3) Uani 1 1 d . . . H5 H 0.4152 0.3471 0.9533 0.038(4) Uiso 1 1 calc R . . C6 C 0.41337(12) 0.33670(10) 1.06716(7) 0.0257(3) Uani 1 1 d . . . H6 H 0.5109 0.3627 1.0800 0.046(4) Uiso 1 1 calc R . . C7 C 0.14064(12) 0.61194(10) 0.83748(6) 0.0216(3) Uani 1 1 d . . . C8 C 0.24152(12) 0.57144(10) 0.81219(7) 0.0222(3) Uani 1 1 d . . . C9 C 0.24509(12) 0.46602(10) 0.82712(7) 0.0229(3) Uani 1 1 d . . . H9 H 0.3143 0.4397 0.8087 0.030(4) Uiso 1 1 calc R . . C10 C 0.14925(12) 0.39710(10) 0.86869(6) 0.0217(3) Uani 1 1 d . . . C11 C 0.05129(12) 0.44075(11) 0.89564(7) 0.0261(3) Uani 1 1 d . . . H11 H -0.0134 0.3974 0.9255 0.031(4) Uiso 1 1 calc R . . C12 C 0.04618(13) 0.54588(11) 0.87988(7) 0.0259(3) Uani 1 1 d . . . H12 H -0.0225 0.5728 0.8983 0.033(4) Uiso 1 1 calc R . . C13 C 0.15262(12) 0.27960(10) 0.88551(6) 0.0216(3) Uani 1 1 d . . . C14 C 0.24079(12) 0.23834(10) 0.83208(7) 0.0252(3) Uani 1 1 d . . . H14A H 0.2062 0.2434 0.7785 0.030(4) Uiso 1 1 calc R . . H14B H 0.3375 0.2884 0.8425 0.031(4) Uiso 1 1 calc R . . C15 C 0.23820(14) 0.11874(11) 0.84147(8) 0.0325(3) Uani 1 1 d . . . H15A H 0.2786 0.1141 0.8940 0.037(4) Uiso 1 1 calc R . . H15B H 0.2952 0.0969 0.8055 0.039(4) Uiso 1 1 calc R . . C16 C 0.09107(15) 0.03804(12) 0.82629(9) 0.0392(4) Uani 1 1 d . . . H16A H 0.0547 0.0356 0.7719 0.040(4) Uiso 1 1 calc R . . H16B H 0.0915 -0.0381 0.8367 0.048(5) Uiso 1 1 calc R . . C17 C -0.00259(14) 0.07417(11) 0.87646(8) 0.0338(3) Uani 1 1 d . . . H17A H 0.0258 0.0660 0.9304 0.032(4) Uiso 1 1 calc R . . H17B H -0.0989 0.0248 0.8621 0.043(4) Uiso 1 1 calc R . . C18 C 0.00402(12) 0.19541(11) 0.86813(7) 0.0274(3) Uani 1 1 d . . . H18A H -0.0549 0.2165 0.9032 0.033(4) Uiso 1 1 calc R . . H18B H -0.0343 0.2012 0.8154 0.032(4) Uiso 1 1 calc R . . C19 C -0.32023(12) 0.17680(9) 0.36892(6) 0.0205(2) Uani 1 1 d . . . C20 C -0.17858(12) 0.21941(9) 0.39020(7) 0.0198(2) Uani 1 1 d . . . C21 C -0.12400(12) 0.23821(9) 0.46691(7) 0.0202(2) Uani 1 1 d . . . H21 H -0.0268 0.2682 0.4806 0.026(3) Uiso 1 1 calc R . . C22 C -0.20986(12) 0.21360(9) 0.52424(6) 0.0194(2) Uani 1 1 d . . . C23 C -0.35172(12) 0.16894(10) 0.50136(7) 0.0241(3) Uani 1 1 d . . . H23 H -0.4124 0.1501 0.5390 0.035(4) Uiso 1 1 calc R . . C24 C -0.40644(12) 0.15129(10) 0.42496(7) 0.0244(3) Uani 1 1 d . . . H24 H -0.5036 0.1216 0.4110 0.039(4) Uiso 1 1 calc R . . C25 C -0.15425(12) -0.10463(10) 0.66528(6) 0.0206(2) Uani 1 1 d . . . C26 C -0.24966(11) -0.05871(10) 0.69188(6) 0.0202(2) Uani 1 1 d . . . C27 C -0.24863(11) 0.04761(10) 0.67508(6) 0.0210(3) Uani 1 1 d . . . H27 H -0.3137 0.0782 0.6943 0.029(4) Uiso 1 1 calc R . . C28 C -0.15406(12) 0.11062(10) 0.63050(6) 0.0206(2) Uani 1 1 d . . . C29 C -0.06134(12) 0.06154(10) 0.60248(7) 0.0245(3) Uani 1 1 d . . . H29 H 0.0025 0.1013 0.5708 0.033(4) Uiso 1 1 calc R . . C30 C -0.06083(12) -0.04373(10) 0.62008(7) 0.0244(3) Uani 1 1 d . . . H30 H 0.0041 -0.0746 0.6010 0.035(4) Uiso 1 1 calc R . . C31 C -0.15287(11) 0.22749(10) 0.60973(6) 0.0202(2) Uani 1 1 d . . . C32 C -0.24268(13) 0.27472(10) 0.65853(7) 0.0249(3) Uani 1 1 d . . . H32A H -0.3399 0.2260 0.6474 0.029(4) Uiso 1 1 calc R . . H32B H -0.2117 0.2731 0.7132 0.027(4) Uiso 1 1 calc R . . C33 C -0.23505(14) 0.39407(11) 0.64350(8) 0.0340(3) Uani 1 1 d . . . H33A H -0.2697 0.3957 0.5894 0.043(4) Uiso 1 1 calc R . . H33B H -0.2948 0.4198 0.6756 0.048(5) Uiso 1 1 calc R . . C34 C -0.08740(15) 0.47264(12) 0.66117(9) 0.0401(4) Uani 1 1 d . . . H34A H -0.0560 0.4772 0.7164 0.048(5) Uiso 1 1 calc R . . H34B H -0.0841 0.5486 0.6481 0.048(5) Uiso 1 1 calc R . . C35 C 0.00868(14) 0.43108(11) 0.61569(8) 0.0340(3) Uani 1 1 d . . . H35A H 0.1052 0.4790 0.6316 0.044(4) Uiso 1 1 calc R . . H35B H -0.0146 0.4372 0.5607 0.036(4) Uiso 1 1 calc R . . C36 C -0.00333(12) 0.30968(10) 0.62778(7) 0.0265(3) Uani 1 1 d . . . H36A H 0.0318 0.3060 0.6815 0.036(4) Uiso 1 1 calc R . . H36B H 0.0563 0.2850 0.5950 0.030(4) Uiso 1 1 calc R . . C37 C -0.63236(16) 0.44800(13) 0.58078(9) 0.0422(4) Uani 1 1 d . . . C38 C -0.68727(18) 0.36980(17) 0.51896(10) 0.0525(4) Uani 1 1 d . . . H38 H -0.7149 0.3931 0.4715 0.091(7) Uiso 1 1 calc R . . C39 C -0.70295(16) 0.25780(16) 0.52465(10) 0.0534(5) Uani 1 1 d . . . H39 H -0.7399 0.2060 0.4808 0.066(6) Uiso 1 1 calc R . . C40 C -0.66571(14) 0.21937(13) 0.59328(10) 0.0421(4) Uani 1 1 d . . . C41 C -0.61031(15) 0.29857(13) 0.65508(9) 0.0379(3) Uani 1 1 d . . . H41 H -0.5831 0.2760 0.7029 0.056(5) Uiso 1 1 calc R . . C42 C -0.59418(16) 0.40997(13) 0.64803(9) 0.0388(3) Uani 1 1 d . . . H42 H -0.5551 0.4624 0.6914 0.059(5) Uiso 1 1 calc R . . C43 C -0.6138(2) 0.57131(17) 0.57578(15) 0.0705(7) Uani 1 1 d . . . H43A H -0.5783 0.5940 0.5279 0.138(11) Uiso 1 1 calc R . . H43B H -0.5482 0.6153 0.6190 0.23(2) Uiso 1 1 calc R . . H43C H -0.7030 0.5842 0.5772 0.192(15) Uiso 1 1 calc R . . C44 C -0.6842(2) 0.09804(15) 0.60157(16) 0.0741(7) Uani 1 1 d . . . H44A H -0.7177 0.0549 0.5517 0.123(10) Uiso 1 1 calc R . . H44B H -0.7515 0.0705 0.6371 0.111(9) Uiso 1 1 calc R . . H44C H -0.5955 0.0896 0.6213 0.159(13) Uiso 1 1 calc R . . C45 C 0.65893(14) 0.30083(12) 0.88879(9) 0.0374(3) Uani 1 1 d . . . C46 C 0.61294(14) 0.20458(12) 0.83981(8) 0.0337(3) Uani 1 1 d . . . H46 H 0.5807 0.2084 0.7881 0.042(4) Uiso 1 1 calc R . . C47 C 0.61253(16) 0.10219(13) 0.86418(9) 0.0408(4) Uani 1 1 d . . . H47 H 0.5804 0.0372 0.8289 0.060(5) Uiso 1 1 calc R . . C48 C 0.65824(17) 0.09330(17) 0.93903(11) 0.0535(5) Uani 1 1 d . . . C49 C 0.70221(18) 0.1907(2) 0.98864(10) 0.0627(6) Uani 1 1 d . . . H49 H 0.7327 0.1873 1.0407 0.085(6) Uiso 1 1 calc R . . C50 C 0.70224(16) 0.29167(17) 0.96356(10) 0.0546(5) Uani 1 1 d . . . H50 H 0.7329 0.3567 0.9987 0.091(7) Uiso 1 1 calc R . . C51 C 0.6626(2) 0.41213(15) 0.86103(15) 0.0698(6) Uani 1 1 d . . . H51A H 0.6836 0.4685 0.9048 0.143(11) Uiso 1 1 calc R . . H51B H 0.5726 0.4060 0.8331 0.169(13) Uiso 1 1 calc R . . H51C H 0.7341 0.4344 0.8272 0.091(7) Uiso 1 1 calc R . . C52 C 0.6599(3) -0.0187(3) 0.9646(2) 0.1141(13) Uani 1 1 d . . . H52A H 0.6128 -0.0331 1.0101 0.137(10) Uiso 1 1 calc R . . H52B H 0.7556 -0.0178 0.9765 0.183(14) Uiso 1 1 calc R . . H52C H 0.6122 -0.0778 0.9236 0.21(2) 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 0.0200(4) 0.0339(5) 0.0202(4) 0.0087(3) 0.0017(3) 0.0050(4) O2 0.0209(4) 0.0429(5) 0.0208(4) 0.0125(4) 0.0075(3) 0.0101(4) O7 0.0263(5) 0.0294(5) 0.0266(5) 0.0096(4) 0.0079(4) 0.0117(4) O8 0.0201(4) 0.0316(5) 0.0358(5) 0.0175(4) 0.0103(4) 0.0077(4) O19 0.0207(5) 0.0334(5) 0.0214(4) 0.0075(4) 0.0008(3) 0.0046(4) O20 0.0197(4) 0.0379(5) 0.0207(4) 0.0095(4) 0.0059(3) 0.0094(4) O25 0.0261(5) 0.0261(5) 0.0278(5) 0.0103(4) 0.0079(4) 0.0109(4) O26 0.0202(4) 0.0279(5) 0.0299(5) 0.0131(4) 0.0098(3) 0.0072(4) C1 0.0212(6) 0.0198(6) 0.0202(6) 0.0058(4) 0.0021(4) 0.0061(5) C2 0.0205(6) 0.0199(6) 0.0222(6) 0.0071(4) 0.0077(5) 0.0067(5) C3 0.0159(6) 0.0240(6) 0.0237(6) 0.0054(5) 0.0036(4) 0.0052(5) C4 0.0206(6) 0.0200(6) 0.0200(6) 0.0052(4) 0.0025(4) 0.0055(5) C5 0.0191(6) 0.0344(7) 0.0214(6) 0.0069(5) 0.0062(5) 0.0031(5) C6 0.0164(6) 0.0323(7) 0.0257(6) 0.0073(5) 0.0033(5) 0.0029(5) C7 0.0219(6) 0.0241(6) 0.0180(6) 0.0052(4) -0.0001(4) 0.0066(5) C8 0.0157(6) 0.0292(6) 0.0196(6) 0.0067(5) 0.0029(4) 0.0031(5) C9 0.0171(6) 0.0299(6) 0.0220(6) 0.0067(5) 0.0034(5) 0.0068(5) C10 0.0181(6) 0.0276(6) 0.0175(6) 0.0052(4) 0.0011(4) 0.0044(5) C11 0.0226(6) 0.0322(7) 0.0242(6) 0.0096(5) 0.0095(5) 0.0064(5) C12 0.0227(6) 0.0344(7) 0.0245(6) 0.0077(5) 0.0081(5) 0.0120(5) C13 0.0193(6) 0.0249(6) 0.0189(6) 0.0058(4) 0.0033(4) 0.0038(5) C14 0.0237(6) 0.0291(7) 0.0210(6) 0.0028(5) 0.0040(5) 0.0053(5) C15 0.0347(7) 0.0285(7) 0.0340(7) 0.0003(5) 0.0058(6) 0.0094(6) C16 0.0416(8) 0.0286(7) 0.0403(8) -0.0026(6) 0.0046(7) 0.0022(6) C17 0.0312(7) 0.0270(7) 0.0345(8) 0.0026(5) 0.0020(6) -0.0026(5) C18 0.0201(6) 0.0328(7) 0.0238(6) 0.0058(5) 0.0000(5) 0.0009(5) C19 0.0229(6) 0.0188(6) 0.0198(6) 0.0058(4) 0.0016(5) 0.0062(5) C20 0.0203(6) 0.0185(6) 0.0229(6) 0.0073(4) 0.0076(5) 0.0071(5) C21 0.0161(6) 0.0211(6) 0.0234(6) 0.0051(4) 0.0025(4) 0.0054(4) C22 0.0211(6) 0.0176(5) 0.0199(6) 0.0052(4) 0.0035(4) 0.0060(5) C23 0.0198(6) 0.0282(6) 0.0232(6) 0.0069(5) 0.0056(5) 0.0039(5) C24 0.0169(6) 0.0276(6) 0.0263(6) 0.0073(5) 0.0030(5) 0.0026(5) C25 0.0206(6) 0.0232(6) 0.0173(5) 0.0043(4) 0.0006(4) 0.0061(5) C26 0.0151(5) 0.0254(6) 0.0173(5) 0.0055(4) 0.0019(4) 0.0017(5) C27 0.0166(6) 0.0265(6) 0.0203(6) 0.0041(5) 0.0037(4) 0.0064(5) C28 0.0187(6) 0.0241(6) 0.0173(5) 0.0038(4) 0.0012(4) 0.0046(5) C29 0.0238(6) 0.0299(7) 0.0216(6) 0.0089(5) 0.0086(5) 0.0083(5) C30 0.0228(6) 0.0307(7) 0.0231(6) 0.0062(5) 0.0073(5) 0.0115(5) C31 0.0182(6) 0.0220(6) 0.0189(6) 0.0046(4) 0.0033(4) 0.0036(5) C32 0.0245(6) 0.0244(6) 0.0246(6) 0.0007(5) 0.0046(5) 0.0060(5) C33 0.0370(8) 0.0258(7) 0.0391(8) -0.0018(6) 0.0061(6) 0.0101(6) C34 0.0438(9) 0.0239(7) 0.0463(9) -0.0040(6) 0.0055(7) 0.0031(6) C35 0.0311(7) 0.0258(7) 0.0375(8) 0.0030(5) 0.0038(6) -0.0020(5) C36 0.0209(6) 0.0290(7) 0.0249(6) 0.0041(5) 0.0005(5) 0.0019(5) C37 0.0423(9) 0.0476(9) 0.0471(9) 0.0173(7) 0.0228(7) 0.0216(7) C38 0.0479(10) 0.0772(13) 0.0391(9) 0.0174(9) 0.0107(7) 0.0255(9) C39 0.0345(9) 0.0695(12) 0.0458(10) -0.0196(9) 0.0041(7) 0.0062(8) C40 0.0258(7) 0.0366(8) 0.0648(11) -0.0012(7) 0.0177(7) 0.0085(6) C41 0.0389(8) 0.0431(8) 0.0383(8) 0.0114(6) 0.0113(6) 0.0191(7) C42 0.0440(9) 0.0399(8) 0.0367(8) 0.0011(6) 0.0118(7) 0.0176(7) C43 0.0772(15) 0.0555(12) 0.1020(18) 0.0415(12) 0.0490(14) 0.0365(11) C44 0.0439(11) 0.0357(10) 0.144(2) 0.0023(12) 0.0372(13) 0.0071(8) C45 0.0235(7) 0.0374(8) 0.0511(9) -0.0014(6) 0.0135(6) 0.0074(6) C46 0.0335(7) 0.0413(8) 0.0275(7) 0.0057(6) 0.0062(6) 0.0124(6) C47 0.0457(9) 0.0361(8) 0.0448(9) 0.0044(7) 0.0188(7) 0.0146(7) C48 0.0417(9) 0.0773(13) 0.0619(12) 0.0416(10) 0.0298(8) 0.0345(9) C49 0.0390(10) 0.1237(19) 0.0283(9) 0.0169(10) 0.0065(7) 0.0277(11) C50 0.0307(8) 0.0799(13) 0.0427(10) -0.0211(9) 0.0058(7) 0.0066(8) C51 0.0476(11) 0.0375(10) 0.129(2) 0.0139(11) 0.0382(12) 0.0108(8) C52 0.104(2) 0.138(3) 0.161(3) 0.122(3) 0.085(2) 0.084(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 O1 C1 1.3811(14) . ? O1 H1O 0.9085 . ? O2 C2 1.3854(13) . ? O2 H2O 0.9055 . ? O7 C7 1.3792(15) . ? O7 H7O 0.8475 . ? O8 C8 1.3833(13) . ? O8 H8O 0.9194 . ? O19 C19 1.3839(14) . ? O19 H19O 0.8400 . ? O20 C20 1.3830(13) . ? O20 H20O 0.9409 . ? O25 C25 1.3819(15) . ? O25 H25O 0.9408 . ? O26 C26 1.3835(13) . ? O26 H26O 0.9822 . ? C1 C6 1.3835(16) . ? C1 C2 1.3864(17) . ? C2 C3 1.3855(17) . ? C3 C4 1.3988(16) . ? C3 H3 0.9500 . ? C4 C5 1.3934(17) . ? C4 C13 1.5449(16) . ? C5 C6 1.3892(17) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.3872(16) . ? C7 C8 1.3897(17) . ? C8 C9 1.3827(17) . ? C9 C10 1.4012(16) . ? C9 H9 0.9500 . ? C10 C11 1.3979(17) . ? C10 C13 1.5399(17) . ? C11 C12 1.3875(18) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.5487(17) . ? C13 C18 1.5542(16) . ? C14 C15 1.5212(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.525(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.524(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.5278(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.3839(16) . ? C19 C20 1.3874(17) . ? C20 C21 1.3914(16) . ? C21 C22 1.3991(16) . ? C21 H21 0.9500 . ? C22 C23 1.3950(17) . ? C22 C31 1.5439(16) . ? C23 C24 1.3869(17) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.3900(17) . ? C25 C30 1.3881(16) . ? C26 C27 1.3888(17) . ? C27 C28 1.3978(15) . ? C27 H27 0.9500 . ? C28 C29 1.4011(17) . ? C28 C31 1.5380(17) . ? C29 C30 1.3840(18) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.5487(16) . ? C31 C36 1.5530(16) . ? C32 C33 1.5251(18) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.522(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.527(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.5290(19) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C42 1.373(2) . ? C37 C38 1.376(2) . ? C37 C43 1.518(2) . ? C38 C39 1.384(3) . ? C38 H38 0.9500 . ? C39 C40 1.394(2) . ? C39 H39 0.9500 . ? C40 C41 1.384(2) . ? C40 C44 1.502(2) . ? C41 C42 1.379(2) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C50 1.374(2) . ? C45 C46 1.375(2) . ? C45 C51 1.506(2) . ? C46 C47 1.385(2) . ? C46 H46 0.9500 . ? C47 C48 1.381(2) . ? C47 H47 0.9500 . ? C48 C49 1.392(3) . ? C48 C52 1.514(3) . ? C49 C50 1.374(3) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 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 C1 O1 H1O 109.2 . . ? C2 O2 H2O 112.5 . . ? C7 O7 H7O 111.1 . . ? C8 O8 H8O 112.9 . . ? C19 O19 H19O 109.5 . . ? C20 O20 H20O 109.3 . . ? C25 O25 H25O 109.2 . . ? C26 O26 H26O 110.7 . . ? O1 C1 C6 123.94(11) . . ? O1 C1 C2 117.23(10) . . ? C6 C1 C2 118.83(11) . . ? O2 C2 C3 118.60(10) . . ? O2 C2 C1 120.58(11) . . ? C3 C2 C1 120.82(10) . . ? C2 C3 C4 121.15(11) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 117.19(11) . . ? C5 C4 C13 120.46(10) . . ? C3 C4 C13 122.31(10) . . ? C6 C5 C4 121.71(11) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C1 C6 C5 120.29(11) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O7 C7 C12 124.10(11) . . ? O7 C7 C8 117.21(10) . . ? C12 C7 C8 118.70(11) . . ? C9 C8 O8 118.30(10) . . ? C9 C8 C7 120.60(10) . . ? O8 C8 C7 121.10(11) . . ? C8 C9 C10 121.65(11) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 116.85(11) . . ? C11 C10 C13 121.22(10) . . ? C9 C10 C13 121.92(11) . . ? C12 C11 C10 121.65(11) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C7 120.51(11) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C10 C13 C4 107.20(9) . . ? C10 C13 C14 110.78(9) . . ? C4 C13 C14 111.05(10) . . ? C10 C13 C18 109.21(10) . . ? C4 C13 C18 112.42(9) . . ? C14 C13 C18 106.21(10) . . ? C15 C14 C13 113.19(10) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C16 111.09(12) . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C15 110.93(12) . . ? C17 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 111.45(11) . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C17 C18 C13 113.50(10) . . ? C17 C18 H18A 108.9 . . ? C13 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C13 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? O19 C19 C24 123.75(11) . . ? O19 C19 C20 117.13(10) . . ? C24 C19 C20 119.12(11) . . ? O20 C20 C19 120.96(11) . . ? O20 C20 C21 118.57(10) . . ? C19 C20 C21 120.47(10) . . ? C20 C21 C22 121.08(11) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 117.37(11) . . ? C23 C22 C31 119.94(10) . . ? C21 C22 C31 122.59(10) . . ? C24 C23 C22 121.64(11) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C19 C24 C23 120.31(11) . . ? C19 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? O25 C25 C26 117.59(10) . . ? O25 C25 C30 123.52(10) . . ? C26 C25 C30 118.89(11) . . ? O26 C26 C27 118.05(10) . . ? O26 C26 C25 121.64(10) . . ? C27 C26 C25 120.31(10) . . ? C26 C27 C28 121.49(11) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C27 C28 C29 117.27(11) . . ? C27 C28 C31 122.45(10) . . ? C29 C28 C31 120.24(10) . . ? C30 C29 C28 121.32(11) . . ? C30 C29 H29 119.3 . . ? C28 C29 H29 119.3 . . ? C29 C30 C25 120.68(11) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? C28 C31 C22 106.15(9) . . ? C28 C31 C32 111.46(9) . . ? C22 C31 C32 110.77(10) . . ? C28 C31 C36 109.16(10) . . ? C22 C31 C36 113.02(9) . . ? C32 C31 C36 106.35(10) . . ? C33 C32 C31 112.73(10) . . ? C33 C32 H32A 109.0 . . ? C31 C32 H32A 109.0 . . ? C33 C32 H32B 109.0 . . ? C31 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? C34 C33 C32 110.96(12) . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C33 C34 C35 110.54(12) . . ? C33 C34 H34A 109.5 . . ? C35 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? C35 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? C34 C35 C36 111.62(11) . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? C35 C36 C31 113.90(10) . . ? C35 C36 H36A 108.8 . . ? C31 C36 H36A 108.8 . . ? C35 C36 H36B 108.8 . . ? C31 C36 H36B 108.8 . . ? H36A C36 H36B 107.7 . . ? C42 C37 C38 117.11(15) . . ? C42 C37 C43 120.79(17) . . ? C38 C37 C43 122.10(17) . . ? C37 C38 C39 121.21(16) . . ? C37 C38 H38 119.4 . . ? C39 C38 H38 119.4 . . ? C38 C39 C40 121.48(15) . . ? C38 C39 H39 119.3 . . ? C40 C39 H39 119.3 . . ? C41 C40 C39 116.93(15) . . ? C41 C40 C44 120.40(18) . . ? C39 C40 C44 122.67(17) . . ? C42 C41 C40 120.70(15) . . ? C42 C41 H41 119.6 . . ? C40 C41 H41 119.6 . . ? C37 C42 C41 122.56(15) . . ? C37 C42 H42 118.7 . . ? C41 C42 H42 118.7 . . ? C37 C43 H43A 109.5 . . ? C37 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C37 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C40 C44 H44A 109.5 . . ? C40 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C40 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C50 C45 C46 117.58(15) . . ? C50 C45 C51 121.42(16) . . ? C46 C45 C51 121.00(16) . . ? C45 C46 C47 121.54(14) . . ? C45 C46 H46 119.2 . . ? C47 C46 H46 119.2 . . ? C48 C47 C46 120.87(15) . . ? C48 C47 H47 119.6 . . ? C46 C47 H47 119.6 . . ? C47 C48 C49 117.29(16) . . ? C47 C48 C52 120.3(2) . . ? C49 C48 C52 122.4(2) . . ? C50 C49 C48 121.14(16) . . ? C50 C49 H49 119.4 . . ? C48 C49 H49 119.4 . . ? C49 C50 C45 121.56(16) . . ? C49 C50 H50 119.2 . . ? C45 C50 H50 119.2 . . ? C45 C51 H51A 109.5 . . ? C45 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C45 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C48 C52 H52A 109.5 . . ? C48 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C48 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 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 O1 C1 C2 O2 0.73(16) . . . . ? C6 C1 C2 O2 -178.95(11) . . . . ? O1 C1 C2 C3 -179.82(10) . . . . ? C6 C1 C2 C3 0.50(17) . . . . ? O2 C2 C3 C4 179.23(10) . . . . ? C1 C2 C3 C4 -0.23(18) . . . . ? C2 C3 C4 C5 -0.56(17) . . . . ? C2 C3 C4 C13 -178.17(10) . . . . ? C3 C4 C5 C6 1.11(18) . . . . ? C13 C4 C5 C6 178.77(11) . . . . ? O1 C1 C6 C5 -179.62(11) . . . . ? C2 C1 C6 C5 0.04(18) . . . . ? C4 C5 C6 C1 -0.87(19) . . . . ? O7 C7 C8 C9 -178.10(10) . . . . ? C12 C7 C8 C9 1.87(18) . . . . ? O7 C7 C8 O8 2.15(16) . . . . ? C12 C7 C8 O8 -177.88(11) . . . . ? O8 C8 C9 C10 178.97(10) . . . . ? C7 C8 C9 C10 -0.79(18) . . . . ? C8 C9 C10 C11 -1.17(17) . . . . ? C8 C9 C10 C13 179.99(11) . . . . ? C9 C10 C11 C12 2.08(18) . . . . ? C13 C10 C11 C12 -179.07(11) . . . . ? C10 C11 C12 C7 -1.04(19) . . . . ? O7 C7 C12 C11 178.99(11) . . . . ? C8 C7 C12 C11 -0.97(18) . . . . ? C11 C10 C13 C4 -74.44(14) . . . . ? C9 C10 C13 C4 104.35(12) . . . . ? C11 C10 C13 C14 164.25(11) . . . . ? C9 C10 C13 C14 -16.96(15) . . . . ? C11 C10 C13 C18 47.60(15) . . . . ? C9 C10 C13 C18 -133.61(11) . . . . ? C5 C4 C13 C10 -81.80(13) . . . . ? C3 C4 C13 C10 95.74(12) . . . . ? C5 C4 C13 C14 39.34(15) . . . . ? C3 C4 C13 C14 -143.12(11) . . . . ? C5 C4 C13 C18 158.18(11) . . . . ? C3 C4 C13 C18 -24.28(16) . . . . ? C10 C13 C14 C15 -175.19(10) . . . . ? C4 C13 C14 C15 65.80(13) . . . . ? C18 C13 C14 C15 -56.72(13) . . . . ? C13 C14 C15 C16 58.40(15) . . . . ? C14 C15 C16 C17 -54.75(16) . . . . ? C15 C16 C17 C18 53.68(16) . . . . ? C16 C17 C18 C13 -56.17(15) . . . . ? C10 C13 C18 C17 175.09(10) . . . . ? C4 C13 C18 C17 -66.07(14) . . . . ? C14 C13 C18 C17 55.58(13) . . . . ? O19 C19 C20 O20 -1.39(16) . . . . ? C24 C19 C20 O20 178.71(10) . . . . ? O19 C19 C20 C21 178.73(10) . . . . ? C24 C19 C20 C21 -1.18(17) . . . . ? O20 C20 C21 C22 -179.15(10) . . . . ? C19 C20 C21 C22 0.73(17) . . . . ? C20 C21 C22 C23 0.43(17) . . . . ? C20 C21 C22 C31 176.73(10) . . . . ? C21 C22 C23 C24 -1.15(17) . . . . ? C31 C22 C23 C24 -177.56(11) . . . . ? O19 C19 C24 C23 -179.44(11) . . . . ? C20 C19 C24 C23 0.46(18) . . . . ? C22 C23 C24 C19 0.73(19) . . . . ? O25 C25 C26 O26 -1.78(16) . . . . ? C30 C25 C26 O26 178.04(10) . . . . ? O25 C25 C26 C27 178.45(10) . . . . ? C30 C25 C26 C27 -1.73(17) . . . . ? O26 C26 C27 C28 -178.87(10) . . . . ? C25 C26 C27 C28 0.91(17) . . . . ? C26 C27 C28 C29 0.86(17) . . . . ? C26 C27 C28 C31 178.68(10) . . . . ? C27 C28 C29 C30 -1.83(18) . . . . ? C31 C28 C29 C30 -179.70(11) . . . . ? C28 C29 C30 C25 1.03(19) . . . . ? O25 C25 C30 C29 -179.42(11) . . . . ? C26 C25 C30 C29 0.78(18) . . . . ? C27 C28 C31 C22 -107.53(12) . . . . ? C29 C28 C31 C22 70.23(13) . . . . ? C27 C28 C31 C32 13.17(15) . . . . ? C29 C28 C31 C32 -169.07(10) . . . . ? C27 C28 C31 C36 130.35(11) . . . . ? C29 C28 C31 C36 -51.89(14) . . . . ? C23 C22 C31 C28 78.12(13) . . . . ? C21 C22 C31 C28 -98.10(12) . . . . ? C23 C22 C31 C32 -43.03(14) . . . . ? C21 C22 C31 C32 140.76(11) . . . . ? C23 C22 C31 C36 -162.25(11) . . . . ? C21 C22 C31 C36 21.54(15) . . . . ? C28 C31 C32 C33 175.70(10) . . . . ? C22 C31 C32 C33 -66.34(13) . . . . ? C36 C31 C32 C33 56.83(13) . . . . ? C31 C32 C33 C34 -59.72(15) . . . . ? C32 C33 C34 C35 55.90(16) . . . . ? C33 C34 C35 C36 -53.60(16) . . . . ? C34 C35 C36 C31 55.16(15) . . . . ? C28 C31 C36 C35 -175.14(10) . . . . ? C22 C31 C36 C35 66.98(13) . . . . ? C32 C31 C36 C35 -54.76(13) . . . . ? C42 C37 C38 C39 -0.1(2) . . . . ? C43 C37 C38 C39 179.82(15) . . . . ? C37 C38 C39 C40 0.9(2) . . . . ? C38 C39 C40 C41 -1.0(2) . . . . ? C38 C39 C40 C44 178.73(14) . . . . ? C39 C40 C41 C42 0.3(2) . . . . ? C44 C40 C41 C42 -179.42(14) . . . . ? C38 C37 C42 C41 -0.6(2) . . . . ? C43 C37 C42 C41 179.48(14) . . . . ? C40 C41 C42 C37 0.5(2) . . . . ? C50 C45 C46 C47 -1.2(2) . . . . ? C51 C45 C46 C47 178.23(14) . . . . ? C45 C46 C47 C48 0.2(2) . . . . ? C46 C47 C48 C49 1.0(2) . . . . ? C46 C47 C48 C52 -178.81(15) . . . . ? C47 C48 C49 C50 -1.1(2) . . . . ? C52 C48 C49 C50 178.68(16) . . . . ? C48 C49 C50 C45 0.1(2) . . . . ? C46 C45 C50 C49 1.1(2) . . . . ? C51 C45 C50 C49 -178.35(15) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.257 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.038