# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 O3.C3.50 H4' _chemical_formula_sum 'C23.50 H20 O3' _chemical_formula_weight 350.40 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3730(1) _cell_length_b 9.0720(2) _cell_length_c 12.6500(3) _cell_angle_alpha 95.470(1) _cell_angle_beta 96.202(1) _cell_angle_gamma 110.315(1) _cell_volume 886.71(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 15400 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 27.10 _exptl_crystal_description block _exptl_crystal_colour colourles _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 370 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9714 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7149 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3853 _reflns_number_gt 3370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0442P)^2^+0.2495P] 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 none _refine_ls_number_reflns 3853 _refine_ls_number_parameters 277 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 O9 O 0.28202(9) 0.78780(8) 0.53165(6) 0.01800(17) Uani 1 1 d D . . H9 H 0.2075(16) 0.6925(11) 0.4852(10) 0.043(4) Uiso 1 1 d D . . O10 O -0.07256(9) 0.48678(8) 0.61763(6) 0.02038(18) Uani 1 1 d . . . O11 O 0.68605(11) 1.33761(9) 0.90552(7) 0.0298(2) Uani 1 1 d . . . C1 C 0.38912(14) 0.62467(12) 0.72329(9) 0.0199(2) Uani 1 1 d . . . H1 H 0.4899 0.7179 0.7357 0.024 Uiso 1 1 calc R . . C2 C 0.39993(14) 0.48401(13) 0.75092(9) 0.0230(2) Uani 1 1 d . . . H2 H 0.5077 0.4808 0.7806 0.028 Uiso 1 1 calc R . . C3 C 0.25247(15) 0.34718(13) 0.73515(9) 0.0239(2) Uani 1 1 d . . . H3 H 0.2596 0.2506 0.7542 0.029 Uiso 1 1 calc R . . C4 C 0.09614(14) 0.35185(12) 0.69185(9) 0.0219(2) Uani 1 1 d . . . H4 H -0.0051 0.2592 0.6818 0.026 Uiso 1 1 calc R . . C5 C -0.26809(13) 0.61445(13) 0.57928(9) 0.0212(2) Uani 1 1 d . . . H5 H -0.3583 0.5135 0.5695 0.025 Uiso 1 1 calc R . . C6 C -0.30444(14) 0.74960(13) 0.56634(9) 0.0224(2) Uani 1 1 d . . . H6 H -0.4201 0.7416 0.5460 0.027 Uiso 1 1 calc R . . C7 C -0.17213(14) 0.89705(13) 0.58301(9) 0.0232(2) Uani 1 1 d . . . H7 H -0.1975 0.9902 0.5757 0.028 Uiso 1 1 calc R . . C8 C -0.00316(14) 0.90831(12) 0.61027(9) 0.0207(2) Uani 1 1 d . . . H8 H 0.0864 1.0098 0.6219 0.025 Uiso 1 1 calc R . . C9 C 0.22388(13) 0.78165(11) 0.63550(8) 0.0158(2) Uani 1 1 d . . . C11 C 0.23283(13) 0.63237(12) 0.67742(8) 0.0163(2) Uani 1 1 d . . . C12 C 0.08849(13) 0.49397(12) 0.66305(8) 0.0175(2) Uani 1 1 d . . . C13 C -0.09778(13) 0.62822(12) 0.60670(8) 0.0175(2) Uani 1 1 d . . . C14 C 0.03810(13) 0.77317(12) 0.62100(8) 0.0166(2) Uani 1 1 d . . . C15 C 0.34535(13) 0.93180(11) 0.70773(8) 0.0159(2) Uani 1 1 d . . . C16 C 0.32104(14) 0.96034(12) 0.81369(8) 0.0190(2) Uani 1 1 d . . . H16 H 0.2265 0.8872 0.8392 0.023 Uiso 1 1 calc R . . C17 C 0.43199(14) 1.09351(12) 0.88326(8) 0.0214(2) Uani 1 1 d . . . H17 H 0.4141 1.1105 0.9556 0.026 Uiso 1 1 calc R . . C18 C 0.56949(14) 1.20146(12) 0.84537(9) 0.0206(2) Uani 1 1 d . . . C19 C 0.59354(14) 1.17584(12) 0.73927(9) 0.0210(2) Uani 1 1 d . . . H19 H 0.6864 1.2503 0.7132 0.025 Uiso 1 1 calc R . . C20 C 0.48270(13) 1.04218(12) 0.67110(8) 0.0189(2) Uani 1 1 d . . . H20 H 0.5005 1.0256 0.5987 0.023 Uiso 1 1 calc R . . C21 C 0.66111(19) 1.36996(15) 1.01356(10) 0.0360(3) Uani 1 1 d . . . H21A H 0.5483 1.3799 1.0142 0.054 Uiso 1 1 calc R . . H21C H 0.7517 1.4694 1.0484 0.054 Uiso 1 1 calc R . . H21B H 0.6661 1.2829 1.0525 0.054 Uiso 1 1 calc R . . C1G C -0.0474(3) 0.9220(3) -0.0369(2) 0.0350(6) Uani 0.50 1 d P A -1 C2G C -0.059(3) 1.050(2) -0.0613(18) 0.053(5) Uani 0.50 1 d P A -1 H2G H -0.1293 1.0381 -0.1282 0.064 Uiso 0.50 1 calc PR A -1 C3G C 0.0100(5) 1.2011(4) -0.0087(4) 0.0623(10) Uani 0.50 1 d P A -1 H3G H -0.0153 1.2845 -0.0379 0.075 Uiso 0.50 1 calc PR A -1 C4G C 0.1174(17) 1.2309(13) 0.0874(11) 0.071(4) Uani 0.50 1 d P A -1 H4G H 0.1680 1.3327 0.1295 0.085 Uiso 0.50 1 calc PR A -1 C5G C 0.1462(4) 1.0845(6) 0.1190(3) 0.0613(11) Uani 0.50 1 d P A -1 H5G H 0.2228 1.0974 0.1833 0.074 Uiso 0.50 1 calc PR A -1 C6G C 0.070(2) 0.934(2) 0.0621(13) 0.0349(19) Uani 0.50 1 d P A -1 H6G H 0.0919 0.8445 0.0847 0.042 Uiso 0.50 1 calc PR A -1 C7G C -0.1420(18) 0.7767(16) -0.1023(10) 0.064(3) Uani 0.50 1 d P A -1 H7G1 H -0.2574 0.7334 -0.0822 0.096 Uiso 0.50 1 calc PR A -1 H7G2 H -0.0829 0.7017 -0.0925 0.096 Uiso 0.50 1 calc PR A -1 H7G3 H -0.1517 0.7937 -0.1777 0.096 Uiso 0.50 1 calc PR A -1 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 O9 0.0182(4) 0.0176(4) 0.0168(4) 0.0014(3) 0.0033(3) 0.0050(3) O10 0.0154(4) 0.0148(3) 0.0291(4) 0.0022(3) -0.0016(3) 0.0048(3) O11 0.0327(5) 0.0216(4) 0.0246(4) -0.0036(3) -0.0041(3) 0.0012(3) C1 0.0177(5) 0.0182(5) 0.0229(5) 0.0019(4) 0.0015(4) 0.0060(4) C2 0.0218(5) 0.0231(5) 0.0254(6) 0.0023(4) -0.0011(4) 0.0114(4) C3 0.0287(6) 0.0180(5) 0.0270(6) 0.0039(4) 0.0010(4) 0.0115(5) C4 0.0217(5) 0.0149(5) 0.0270(6) 0.0027(4) 0.0016(4) 0.0046(4) C5 0.0163(5) 0.0210(5) 0.0236(5) 0.0008(4) 0.0011(4) 0.0047(4) C6 0.0164(5) 0.0282(6) 0.0243(5) 0.0020(4) 0.0009(4) 0.0112(4) C7 0.0229(5) 0.0222(5) 0.0279(6) 0.0036(4) 0.0025(4) 0.0128(4) C8 0.0192(5) 0.0176(5) 0.0250(5) 0.0026(4) 0.0013(4) 0.0070(4) C9 0.0157(5) 0.0152(5) 0.0171(5) 0.0028(4) 0.0033(4) 0.0059(4) C11 0.0174(5) 0.0153(5) 0.0167(5) 0.0014(4) 0.0025(4) 0.0066(4) C12 0.0160(5) 0.0180(5) 0.0185(5) 0.0009(4) 0.0009(4) 0.0070(4) C13 0.0186(5) 0.0163(5) 0.0179(5) 0.0010(4) 0.0017(4) 0.0075(4) C14 0.0161(5) 0.0179(5) 0.0160(5) 0.0015(4) 0.0015(4) 0.0068(4) C15 0.0153(5) 0.0146(5) 0.0188(5) 0.0026(4) 0.0000(4) 0.0072(4) C16 0.0198(5) 0.0169(5) 0.0204(5) 0.0050(4) 0.0035(4) 0.0061(4) C17 0.0274(6) 0.0204(5) 0.0174(5) 0.0030(4) 0.0012(4) 0.0103(4) C18 0.0208(5) 0.0161(5) 0.0225(5) 0.0002(4) -0.0043(4) 0.0068(4) C19 0.0173(5) 0.0183(5) 0.0259(6) 0.0040(4) 0.0031(4) 0.0043(4) C20 0.0180(5) 0.0194(5) 0.0195(5) 0.0025(4) 0.0030(4) 0.0071(4) C21 0.0483(8) 0.0271(6) 0.0230(6) -0.0045(5) -0.0047(5) 0.0068(6) C1G 0.0231(12) 0.0451(16) 0.0323(14) 0.0082(12) 0.0081(10) 0.0052(11) C2G 0.038(6) 0.066(7) 0.062(6) 0.028(4) 0.013(4) 0.021(4) C3G 0.050(2) 0.045(2) 0.102(3) 0.024(2) 0.038(2) 0.0190(18) C4G 0.058(6) 0.043(4) 0.106(9) 0.009(4) 0.053(6) 0.000(3) C5G 0.0322(16) 0.094(3) 0.0298(15) -0.0012(18) 0.0014(12) -0.0080(19) C6G 0.020(3) 0.049(4) 0.041(4) 0.023(3) 0.007(2) 0.013(3) C7G 0.035(3) 0.087(7) 0.055(3) -0.015(4) 0.012(2) 0.008(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 O9 C9 1.4489(12) . ? O9 H9 0.965(2) . ? O10 C12 1.3846(12) . ? O10 C13 1.3877(12) . ? O11 C18 1.3712(13) . ? O11 C21 1.4232(15) . ? C1 C2 1.3846(15) . ? C1 C11 1.4004(14) . ? C1 H1 0.9500 . ? C2 C3 1.3930(16) . ? C2 H2 0.9500 . ? C3 C4 1.3796(16) . ? C3 H3 0.9500 . ? C4 C12 1.3932(14) . ? C4 H4 0.9500 . ? C5 C6 1.3818(15) . ? C5 C13 1.3895(15) . ? C5 H5 0.9500 . ? C6 C7 1.3884(16) . ? C6 H6 0.9500 . ? C7 C8 1.3851(15) . ? C7 H7 0.9500 . ? C8 C14 1.3987(14) . ? C8 H8 0.9500 . ? C9 C14 1.5205(13) . ? C9 C11 1.5231(13) . ? C9 C15 1.5247(14) . ? C11 C12 1.3876(14) . ? C13 C14 1.3884(14) . ? C15 C16 1.3908(14) . ? C15 C20 1.3943(14) . ? C16 C17 1.3923(15) . ? C16 H16 0.9500 . ? C17 C18 1.3930(16) . ? C17 H17 0.9500 . ? C18 C19 1.3883(15) . ? C19 C20 1.3862(15) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21C 0.9800 . ? C21 H21B 0.9800 . ? C1G C2G 1.26(2) . ? C1G C7G 1.405(12) . ? C1G C6G 1.479(19) . ? C2G C3G 1.36(2) . ? C2G H2G 0.9500 . ? C3G C4G 1.376(15) . ? C3G H3G 0.9500 . ? C4G C5G 1.512(15) . ? C4G H4G 0.9500 . ? C5G C6G 1.380(19) . ? C5G H5G 0.9500 . ? C6G H6G 0.9500 . ? C7G H7G1 0.9800 . ? C7G H7G2 0.9800 . ? C7G H7G3 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 C9 O9 H9 107.3(10) . . ? C12 O10 C13 118.36(8) . . ? C18 O11 C21 116.79(9) . . ? C2 C1 C11 121.40(10) . . ? C2 C1 H1 119.3 . . ? C11 C1 H1 119.3 . . ? C1 C2 C3 119.86(10) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 120.02(10) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C12 119.22(10) . . ? C3 C4 H4 120.4 . . ? C12 C4 H4 120.4 . . ? C6 C5 C13 119.09(10) . . ? C6 C5 H5 120.5 . . ? C13 C5 H5 120.5 . . ? C5 C6 C7 120.06(10) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 119.98(10) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C14 121.27(10) . . ? C7 C8 H8 119.4 . . ? C14 C8 H8 119.4 . . ? O9 C9 C14 108.45(8) . . ? O9 C9 C11 108.44(8) . . ? C14 C9 C11 109.37(8) . . ? O9 C9 C15 106.23(8) . . ? C14 C9 C15 112.51(8) . . ? C11 C9 C15 111.68(8) . . ? C12 C11 C1 117.21(9) . . ? C12 C11 C9 121.00(9) . . ? C1 C11 C9 121.55(9) . . ? O10 C12 C11 122.40(9) . . ? O10 C12 C4 115.32(9) . . ? C11 C12 C4 122.27(9) . . ? O10 C13 C14 122.25(9) . . ? O10 C13 C5 115.38(9) . . ? C14 C13 C5 122.37(9) . . ? C13 C14 C8 117.19(9) . . ? C13 C14 C9 120.97(9) . . ? C8 C14 C9 121.51(9) . . ? C16 C15 C20 118.38(9) . . ? C16 C15 C9 119.73(9) . . ? C20 C15 C9 121.89(9) . . ? C15 C16 C17 121.58(10) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C16 C17 C18 119.12(10) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? O11 C18 C19 115.50(10) . . ? O11 C18 C17 124.59(10) . . ? C19 C18 C17 119.90(10) . . ? C20 C19 C18 120.34(10) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C15 120.66(10) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? O11 C21 H21A 109.5 . . ? O11 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? O11 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? C2G C1G C7G 120.6(12) . . ? C2G C1G C6G 116.9(15) . . ? C7G C1G C6G 122.5(10) . . ? C1G C2G C3G 131.4(19) . . ? C1G C2G H2G 114.3 . . ? C3G C2G H2G 114.3 . . ? C2G C3G C4G 118.8(11) . . ? C2G C3G H3G 120.6 . . ? C4G C3G H3G 120.6 . . ? C3G C4G C5G 112.9(8) . . ? C3G C4G H4G 123.6 . . ? C5G C4G H4G 123.6 . . ? C6G C5G C4G 125.3(10) . . ? C6G C5G H5G 117.4 . . ? C4G C5G H5G 117.4 . . ? C5G C6G C1G 114.5(15) . . ? C5G C6G H6G 122.7 . . ? C1G C6G H6G 122.7 . . ? 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 C11 C1 C2 C3 -1.32(17) . . . . ? C1 C2 C3 C4 0.16(17) . . . . ? C2 C3 C4 C12 0.83(17) . . . . ? C13 C5 C6 C7 -1.41(16) . . . . ? C5 C6 C7 C8 1.45(17) . . . . ? C6 C7 C8 C14 0.35(17) . . . . ? C2 C1 C11 C12 1.42(15) . . . . ? C2 C1 C11 C9 -173.08(10) . . . . ? O9 C9 C11 C12 -96.13(11) . . . . ? C14 C9 C11 C12 21.96(13) . . . . ? C15 C9 C11 C12 147.16(9) . . . . ? O9 C9 C11 C1 78.17(11) . . . . ? C14 C9 C11 C1 -163.74(9) . . . . ? C15 C9 C11 C1 -38.54(13) . . . . ? C13 O10 C12 C11 -13.55(14) . . . . ? C13 O10 C12 C4 167.39(9) . . . . ? C1 C11 C12 O10 -179.40(9) . . . . ? C9 C11 C12 O10 -4.86(15) . . . . ? C1 C11 C12 C4 -0.41(15) . . . . ? C9 C11 C12 C4 174.13(9) . . . . ? C3 C4 C12 O10 178.36(10) . . . . ? C3 C4 C12 C11 -0.70(16) . . . . ? C12 O10 C13 C14 12.01(14) . . . . ? C12 O10 C13 C5 -168.70(9) . . . . ? C6 C5 C13 O10 -179.72(9) . . . . ? C6 C5 C13 C14 -0.44(16) . . . . ? O10 C13 C14 C8 -178.61(9) . . . . ? C5 C13 C14 C8 2.16(15) . . . . ? O10 C13 C14 C9 7.89(15) . . . . ? C5 C13 C14 C9 -171.35(9) . . . . ? C7 C8 C14 C13 -2.10(16) . . . . ? C7 C8 C14 C9 171.37(10) . . . . ? O9 C9 C14 C13 94.68(11) . . . . ? C11 C9 C14 C13 -23.40(13) . . . . ? C15 C9 C14 C13 -148.12(9) . . . . ? O9 C9 C14 C8 -78.55(11) . . . . ? C11 C9 C14 C8 163.37(9) . . . . ? C15 C9 C14 C8 38.66(13) . . . . ? O9 C9 C15 C16 179.53(8) . . . . ? C14 C9 C15 C16 61.01(12) . . . . ? C11 C9 C15 C16 -62.43(12) . . . . ? O9 C9 C15 C20 -1.10(12) . . . . ? C14 C9 C15 C20 -119.61(10) . . . . ? C11 C9 C15 C20 116.95(10) . . . . ? C20 C15 C16 C17 -1.34(15) . . . . ? C9 C15 C16 C17 178.05(9) . . . . ? C15 C16 C17 C18 0.68(15) . . . . ? C21 O11 C18 C19 177.85(10) . . . . ? C21 O11 C18 C17 -0.97(16) . . . . ? C16 C17 C18 O11 179.20(10) . . . . ? C16 C17 C18 C19 0.43(15) . . . . ? O11 C18 C19 C20 -179.74(9) . . . . ? C17 C18 C19 C20 -0.86(16) . . . . ? C18 C19 C20 C15 0.19(16) . . . . ? C16 C15 C20 C19 0.90(15) . . . . ? C9 C15 C20 C19 -178.48(9) . . . . ? C7G C1G C2G C3G 175.7(15) . . . . ? C6G C1G C2G C3G -5(3) . . . . ? C1G C2G C3G C4G 2(2) . . . . ? C2G C3G C4G C5G 1.7(14) . . . . ? C3G C4G C5G C6G -2.5(14) . . . . ? C4G C5G C6G C1G 0.0(15) . . . . ? C2G C1G C6G C5G 3(2) . . . . ? C7G C1G C6G C5G -177.1(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 O9 H9 O10 0.965(2) 1.902(3) 2.8638(10) 174.2(14) 2_566 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.341 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 934125' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 O3.C3 H2.50 Cl0.5' _chemical_formula_sum 'C23 H18.50 Cl0.50 O3' _chemical_formula_weight 360.60 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3498(2) _cell_length_b 9.0863(2) _cell_length_c 12.6308(3) _cell_angle_alpha 95.767(1) _cell_angle_beta 96.368(1) _cell_angle_gamma 110.027(2) _cell_volume 884.89(4) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 16439 _cell_measurement_theta_min 4.86 _cell_measurement_theta_max 27.11 _exptl_crystal_description block _exptl_crystal_colour colourles _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9608 _exptl_absorpt_correction_T_max 0.9762 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3857 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.86 _diffrn_reflns_theta_max 27.11 _reflns_number_total 3857 _reflns_number_gt 3142 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0381P)^2^+0.3392P] 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 none _refine_ls_number_reflns 3857 _refine_ls_number_parameters 276 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.048 _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 O9 O 0.28191(10) 0.78645(9) 0.53152(6) 0.01745(19) Uani 1 1 d D . . H9 H 0.2061(18) 0.6912(12) 0.4852(11) 0.045(5) Uiso 1 1 d D . . O10 O -0.07168(10) 0.48843(9) 0.61795(7) 0.0199(2) Uani 1 1 d . . . O11 O 0.68870(13) 1.33879(11) 0.90530(7) 0.0301(2) Uani 1 1 d . . . C1 C 0.39128(15) 0.62528(14) 0.72404(10) 0.0194(3) Uani 1 1 d . . . H1 H 0.4921 0.7182 0.7369 0.023 Uiso 1 1 calc R . . C2 C 0.40238(16) 0.48498(15) 0.75136(10) 0.0225(3) Uani 1 1 d . . . H2 H 0.5104 0.4817 0.7814 0.027 Uiso 1 1 calc R . . C3 C 0.25502(17) 0.34857(14) 0.73472(10) 0.0228(3) Uani 1 1 d . . . H3 H 0.2625 0.2521 0.7533 0.027 Uiso 1 1 calc R . . C4 C 0.09848(16) 0.35356(14) 0.69136(10) 0.0214(3) Uani 1 1 d . . . H4 H -0.0027 0.2612 0.6807 0.026 Uiso 1 1 calc R . . C5 C -0.26777(15) 0.61643(14) 0.57959(10) 0.0205(3) Uani 1 1 d . . . H5 H -0.3580 0.5159 0.5698 0.025 Uiso 1 1 calc R . . C6 C -0.30446(16) 0.75126(15) 0.56652(10) 0.0221(3) Uani 1 1 d . . . H6 H -0.4204 0.7436 0.5462 0.027 Uiso 1 1 calc R . . C7 C -0.17188(16) 0.89802(15) 0.58308(10) 0.0226(3) Uani 1 1 d . . . H7 H -0.1973 0.9910 0.5756 0.027 Uiso 1 1 calc R . . C8 C -0.00278(15) 0.90866(14) 0.61050(10) 0.0201(3) Uani 1 1 d . . . H8 H 0.0869 1.0097 0.6221 0.024 Uiso 1 1 calc R . . C9 C 0.22498(14) 0.78152(13) 0.63593(9) 0.0154(2) Uani 1 1 d . . . C11 C 0.23468(15) 0.63319(13) 0.67792(9) 0.0159(2) Uani 1 1 d . . . C12 C 0.09017(15) 0.49528(14) 0.66329(9) 0.0169(2) Uani 1 1 d . . . C13 C -0.09702(15) 0.62975(13) 0.60725(9) 0.0167(2) Uani 1 1 d . . . C14 C 0.03893(14) 0.77404(13) 0.62145(9) 0.0163(2) Uani 1 1 d . . . C15 C 0.34733(14) 0.93205(13) 0.70784(9) 0.0157(2) Uani 1 1 d . . . C16 C 0.32472(16) 0.96135(14) 0.81438(10) 0.0191(3) Uani 1 1 d . . . H16 H 0.2312 0.8884 0.8403 0.023 Uiso 1 1 calc R . . C17 C 0.43574(16) 1.09488(14) 0.88388(10) 0.0213(3) Uani 1 1 d . . . H17 H 0.4188 1.1125 0.9565 0.026 Uiso 1 1 calc R . . C18 C 0.57210(16) 1.20235(14) 0.84539(10) 0.0205(3) Uani 1 1 d . . . C19 C 0.59459(15) 1.17551(14) 0.73894(10) 0.0205(3) Uani 1 1 d . . . H19 H 0.6868 1.2494 0.7126 0.025 Uiso 1 1 calc R . . C20 C 0.48320(15) 1.04135(14) 0.67068(10) 0.0184(2) Uani 1 1 d . . . H20 H 0.5000 1.0241 0.5980 0.022 Uiso 1 1 calc R . . C21 C 0.6642(2) 1.37280(17) 1.01392(11) 0.0372(4) Uani 1 1 d . . . H21A H 0.5500 1.3804 1.0144 0.056 Uiso 1 1 calc R . . H21B H 0.7532 1.4735 1.0482 0.056 Uiso 1 1 calc R . . H21C H 0.6726 1.2878 1.0537 0.056 Uiso 1 1 calc R . . Cl1G Cl 0.1354(2) 1.26971(18) 0.10215(14) 0.0595(4) Uani 0.50 1 d P A -1 C1G C 0.0424(4) 1.0778(4) 0.0333(2) 0.0353(7) Uani 0.50 1 d P A -1 C2G C 0.0816(14) 0.9708(12) 0.0810(8) 0.0314(16) Uani 0.50 1 d P A -1 H2G H 0.1560 0.9965 0.1481 0.038 Uiso 0.50 1 calc PR A -1 C3G C 0.0024(5) 0.8073(6) 0.0235(4) 0.0526(9) Uani 0.50 1 d P A -1 H3G H 0.0232 0.7218 0.0524 0.063 Uiso 0.50 1 calc PR A -1 C4G C -0.1020(11) 0.7829(8) -0.0731(8) 0.093(3) Uani 0.50 1 d P A -1 H4G H -0.1529 0.6779 -0.1106 0.111 Uiso 0.50 1 calc PR A -1 C5G C -0.1371(4) 0.8991(6) -0.1183(3) 0.0530(11) Uani 0.50 1 d P A -1 H5G H -0.2101 0.8762 -0.1857 0.064 Uiso 0.50 1 calc PR A -1 C6G C -0.0570(12) 1.0671(12) -0.0588(7) 0.0271(15) Uani 0.50 1 d P A -1 H6G H -0.0760 1.1552 -0.0847 0.032 Uiso 0.50 1 calc PR A -1 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 O9 0.0183(4) 0.0172(4) 0.0158(4) 0.0013(3) 0.0036(3) 0.0051(3) O10 0.0152(4) 0.0143(4) 0.0286(5) 0.0027(3) -0.0014(3) 0.0050(3) O11 0.0338(5) 0.0212(5) 0.0241(5) -0.0024(4) -0.0048(4) 0.0003(4) C1 0.0169(6) 0.0182(6) 0.0225(6) 0.0023(5) 0.0012(5) 0.0062(5) C2 0.0205(6) 0.0234(6) 0.0254(7) 0.0034(5) -0.0008(5) 0.0114(5) C3 0.0277(7) 0.0172(6) 0.0261(7) 0.0047(5) 0.0019(5) 0.0117(5) C4 0.0221(6) 0.0151(6) 0.0255(6) 0.0029(5) 0.0029(5) 0.0049(5) C5 0.0157(6) 0.0201(6) 0.0232(6) 0.0014(5) 0.0019(5) 0.0043(5) C6 0.0162(6) 0.0280(7) 0.0241(6) 0.0025(5) 0.0012(5) 0.0113(5) C7 0.0220(6) 0.0219(6) 0.0275(7) 0.0040(5) 0.0029(5) 0.0127(5) C8 0.0192(6) 0.0172(6) 0.0237(6) 0.0032(5) 0.0019(5) 0.0067(5) C9 0.0152(5) 0.0154(5) 0.0164(6) 0.0031(4) 0.0029(4) 0.0062(4) C11 0.0163(6) 0.0155(5) 0.0162(6) 0.0011(4) 0.0024(4) 0.0064(4) C12 0.0158(6) 0.0180(6) 0.0175(6) 0.0014(4) 0.0018(4) 0.0075(5) C13 0.0178(6) 0.0158(5) 0.0178(6) 0.0017(4) 0.0026(4) 0.0079(5) C14 0.0156(6) 0.0177(6) 0.0161(6) 0.0018(4) 0.0017(4) 0.0071(5) C15 0.0151(5) 0.0146(5) 0.0187(6) 0.0030(4) 0.0004(4) 0.0076(4) C16 0.0209(6) 0.0167(6) 0.0204(6) 0.0057(5) 0.0040(5) 0.0068(5) C17 0.0287(7) 0.0196(6) 0.0167(6) 0.0033(5) 0.0011(5) 0.0105(5) C18 0.0211(6) 0.0156(6) 0.0223(6) 0.0004(5) -0.0044(5) 0.0064(5) C19 0.0164(6) 0.0180(6) 0.0255(6) 0.0043(5) 0.0032(5) 0.0039(5) C20 0.0173(6) 0.0187(6) 0.0197(6) 0.0025(5) 0.0033(5) 0.0071(5) C21 0.0519(10) 0.0260(7) 0.0222(7) -0.0036(5) -0.0054(6) 0.0050(7) Cl1G 0.0540(7) 0.0449(9) 0.0594(7) -0.0022(6) 0.0156(5) -0.0071(7) C1G 0.0243(14) 0.0426(19) 0.0333(17) 0.0079(14) 0.0076(12) 0.0033(13) C2G 0.022(3) 0.025(5) 0.026(4) -0.007(3) -0.011(2) -0.011(3) C3G 0.039(2) 0.058(3) 0.064(3) 0.019(2) 0.0125(19) 0.018(2) C4G 0.084(6) 0.040(4) 0.133(8) -0.021(4) 0.076(6) -0.014(3) C5G 0.0286(17) 0.084(4) 0.0275(17) 0.008(2) 0.0028(14) -0.0030(19) C6G 0.016(3) 0.023(5) 0.024(4) -0.005(3) -0.008(2) -0.011(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 O9 C9 1.4504(14) . ? O9 H9 0.965(2) . ? O10 C12 1.3863(14) . ? O10 C13 1.3879(14) . ? O11 C18 1.3706(15) . ? O11 C21 1.4283(18) . ? C1 C2 1.3838(17) . ? C1 C11 1.3993(16) . ? C1 H1 0.9500 . ? C2 C3 1.3929(18) . ? C2 H2 0.9500 . ? C3 C4 1.3774(17) . ? C3 H3 0.9500 . ? C4 C12 1.3915(16) . ? C4 H4 0.9500 . ? C5 C6 1.3815(17) . ? C5 C13 1.3901(16) . ? C5 H5 0.9500 . ? C6 C7 1.3889(18) . ? C6 H6 0.9500 . ? C7 C8 1.3836(17) . ? C7 H7 0.9500 . ? C8 C14 1.3971(16) . ? C8 H8 0.9500 . ? C9 C14 1.5210(15) . ? C9 C11 1.5210(15) . ? C9 C15 1.5253(16) . ? C11 C12 1.3888(16) . ? C13 C14 1.3885(16) . ? C15 C20 1.3906(16) . ? C15 C16 1.3915(17) . ? C16 C17 1.3918(17) . ? C16 H16 0.9500 . ? C17 C18 1.3939(18) . ? C17 H17 0.9500 . ? C18 C19 1.3871(18) . ? C19 C20 1.3888(17) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? Cl1G C1G 1.737(3) . ? C1G C2G 1.307(13) . ? C1G C6G 1.327(10) . ? C2G C3G 1.475(7) . ? C2G H2G 0.9500 . ? C3G C4G 1.369(11) . ? C3G H3G 0.9500 . ? C4G C5G 1.349(11) . ? C4G H4G 0.9500 . ? C5G C6G 1.517(8) . ? C5G H5G 0.9500 . ? C6G H6G 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 C9 O9 H9 107.0(11) . . ? C12 O10 C13 118.31(9) . . ? C18 O11 C21 116.73(11) . . ? C2 C1 C11 121.37(11) . . ? C2 C1 H1 119.3 . . ? C11 C1 H1 119.3 . . ? C1 C2 C3 119.90(11) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.99(11) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C12 119.29(11) . . ? C3 C4 H4 120.4 . . ? C12 C4 H4 120.4 . . ? C6 C5 C13 119.12(11) . . ? C6 C5 H5 120.4 . . ? C13 C5 H5 120.4 . . ? C5 C6 C7 120.00(11) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 119.94(11) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C14 121.42(11) . . ? C7 C8 H8 119.3 . . ? C14 C8 H8 119.3 . . ? O9 C9 C14 108.26(9) . . ? O9 C9 C11 108.50(9) . . ? C14 C9 C11 109.56(9) . . ? O9 C9 C15 106.02(9) . . ? C14 C9 C15 112.45(9) . . ? C11 C9 C15 111.86(9) . . ? C12 C11 C1 117.16(10) . . ? C12 C11 C9 120.92(10) . . ? C1 C11 C9 121.69(10) . . ? O10 C12 C11 122.39(10) . . ? O10 C12 C4 115.34(10) . . ? C11 C12 C4 122.26(11) . . ? O10 C13 C14 122.34(10) . . ? O10 C13 C5 115.33(10) . . ? C14 C13 C5 122.32(11) . . ? C13 C14 C8 117.14(10) . . ? C13 C14 C9 120.82(10) . . ? C8 C14 C9 121.70(10) . . ? C20 C15 C16 118.44(11) . . ? C20 C15 C9 122.03(10) . . ? C16 C15 C9 119.53(10) . . ? C15 C16 C17 121.64(11) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C16 C17 C18 119.07(11) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? O11 C18 C19 115.55(11) . . ? O11 C18 C17 124.62(11) . . ? C19 C18 C17 119.82(11) . . ? C18 C19 C20 120.45(11) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C15 120.58(11) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? O11 C21 H21A 109.5 . . ? O11 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O11 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2G C1G C6G 131.7(6) . . ? C2G C1G Cl1G 115.0(3) . . ? C6G C1G Cl1G 113.3(5) . . ? C1G C2G C3G 115.4(7) . . ? C1G C2G H2G 122.3 . . ? C3G C2G H2G 122.3 . . ? C4G C3G C2G 117.8(6) . . ? C4G C3G H3G 121.1 . . ? C2G C3G H3G 121.1 . . ? C5G C4G C3G 123.9(5) . . ? C5G C4G H4G 118.0 . . ? C3G C4G H4G 118.0 . . ? C4G C5G C6G 118.4(6) . . ? C4G C5G H5G 120.8 . . ? C6G C5G H5G 120.8 . . ? C1G C6G C5G 112.8(9) . . ? C1G C6G H6G 123.6 . . ? C5G C6G H6G 123.6 . . ? 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 C11 C1 C2 C3 -1.12(19) . . . . ? C1 C2 C3 C4 -0.15(19) . . . . ? C2 C3 C4 C12 0.85(19) . . . . ? C13 C5 C6 C7 -1.27(18) . . . . ? C5 C6 C7 C8 1.33(19) . . . . ? C6 C7 C8 C14 0.43(19) . . . . ? C2 C1 C11 C12 1.61(17) . . . . ? C2 C1 C11 C9 -172.89(11) . . . . ? O9 C9 C11 C12 -95.85(12) . . . . ? C14 C9 C11 C12 22.15(14) . . . . ? C15 C9 C11 C12 147.55(11) . . . . ? O9 C9 C11 C1 78.43(13) . . . . ? C14 C9 C11 C1 -163.56(10) . . . . ? C15 C9 C11 C1 -38.16(15) . . . . ? C13 O10 C12 C11 -13.37(16) . . . . ? C13 O10 C12 C4 167.76(10) . . . . ? C1 C11 C12 O10 -179.68(10) . . . . ? C9 C11 C12 O10 -5.15(17) . . . . ? C1 C11 C12 C4 -0.89(17) . . . . ? C9 C11 C12 C4 173.65(11) . . . . ? C3 C4 C12 O10 178.55(11) . . . . ? C3 C4 C12 C11 -0.32(18) . . . . ? C12 O10 C13 C14 12.07(16) . . . . ? C12 O10 C13 C5 -168.94(10) . . . . ? C6 C5 C13 O10 -179.53(10) . . . . ? C6 C5 C13 C14 -0.54(18) . . . . ? O10 C13 C14 C8 -178.87(10) . . . . ? C5 C13 C14 C8 2.21(18) . . . . ? O10 C13 C14 C9 7.68(17) . . . . ? C5 C13 C14 C9 -171.24(11) . . . . ? C7 C8 C14 C13 -2.14(18) . . . . ? C7 C8 C14 C9 171.25(11) . . . . ? O9 C9 C14 C13 94.79(12) . . . . ? C11 C9 C14 C13 -23.36(15) . . . . ? C15 C9 C14 C13 -148.42(11) . . . . ? O9 C9 C14 C8 -78.35(13) . . . . ? C11 C9 C14 C8 163.49(11) . . . . ? C15 C9 C14 C8 38.44(15) . . . . ? O9 C9 C15 C20 -0.89(14) . . . . ? C14 C9 C15 C20 -119.01(11) . . . . ? C11 C9 C15 C20 117.20(11) . . . . ? O9 C9 C15 C16 179.83(9) . . . . ? C14 C9 C15 C16 61.71(13) . . . . ? C11 C9 C15 C16 -62.08(13) . . . . ? C20 C15 C16 C17 -1.03(17) . . . . ? C9 C15 C16 C17 178.27(10) . . . . ? C15 C16 C17 C18 0.48(18) . . . . ? C21 O11 C18 C19 177.43(11) . . . . ? C21 O11 C18 C17 -1.44(18) . . . . ? C16 C17 C18 O11 179.21(11) . . . . ? C16 C17 C18 C19 0.38(17) . . . . ? O11 C18 C19 C20 -179.60(11) . . . . ? C17 C18 C19 C20 -0.67(18) . . . . ? C18 C19 C20 C15 0.10(18) . . . . ? C16 C15 C20 C19 0.74(16) . . . . ? C9 C15 C20 C19 -178.55(10) . . . . ? C6G C1G C2G C3G 0.0(19) . . . . ? Cl1G C1G C2G C3G 179.7(6) . . . . ? C1G C2G C3G C4G 0.4(12) . . . . ? C2G C3G C4G C5G -0.3(10) . . . . ? C3G C4G C5G C6G -0.2(10) . . . . ? C2G C1G C6G C5G -0.5(18) . . . . ? Cl1G C1G C6G C5G 179.8(5) . . . . ? C4G C5G C6G C1G 0.6(10) . . . . ? 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 O9 H9 O10 0.965(2) 1.902(3) 2.8633(11) 173.7(16) 2_566 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.11 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.292 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 934126' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 O3.C3 H2.50 Cl0.50' _chemical_formula_sum 'C23 H18.50 Cl0.50 O3' _chemical_formula_weight 360.60 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3670(3) _cell_length_b 9.1032(3) _cell_length_c 12.6727(5) _cell_angle_alpha 95.847(1) _cell_angle_beta 96.491(1) _cell_angle_gamma 110.005(2) _cell_volume 890.91(6) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 15316 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 24.95 _exptl_crystal_description block _exptl_crystal_colour colourles _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9432 _exptl_absorpt_correction_T_max 0.9764 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15316 _diffrn_reflns_av_R_equivalents 0.0681 _diffrn_reflns_av_sigmaI/netI 0.0684 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 24.95 _reflns_number_total 3089 _reflns_number_gt 1884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0621P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 3089 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 O9 O 0.28175(17) 0.78610(16) 0.53187(11) 0.0260(4) Uani 1 1 d D . . H9 H 0.210(3) 0.6885(17) 0.4864(18) 0.072(9) Uiso 1 1 d D . . O10 O -0.07115(16) 0.48908(15) 0.61792(12) 0.0294(4) Uani 1 1 d . . . O11 O 0.68814(19) 1.33797(17) 0.90511(13) 0.0411(5) Uani 1 1 d . . . C1 C 0.3902(3) 0.6248(2) 0.72396(17) 0.0277(5) Uani 1 1 d . . . H1 H 0.4908 0.7175 0.7371 0.033 Uiso 1 1 calc R . . C2 C 0.4014(3) 0.4856(3) 0.75090(18) 0.0324(6) Uani 1 1 d . . . H2 H 0.5094 0.4824 0.7806 0.039 Uiso 1 1 calc R . . C3 C 0.2551(3) 0.3501(3) 0.73464(18) 0.0330(6) Uani 1 1 d . . . H3 H 0.2625 0.2539 0.7535 0.040 Uiso 1 1 calc R . . C4 C 0.0997(3) 0.3553(2) 0.69125(18) 0.0300(6) Uani 1 1 d . . . H4 H -0.0014 0.2631 0.6804 0.036 Uiso 1 1 calc R . . C5 C -0.2665(3) 0.6172(3) 0.57981(17) 0.0292(6) Uani 1 1 d . . . H5 H -0.3566 0.5169 0.5701 0.035 Uiso 1 1 calc R . . C6 C -0.3031(3) 0.7513(3) 0.56680(17) 0.0307(6) Uani 1 1 d . . . H6 H -0.4188 0.7435 0.5465 0.037 Uiso 1 1 calc R . . C7 C -0.1710(3) 0.8976(3) 0.58334(18) 0.0313(6) Uani 1 1 d . . . H7 H -0.1964 0.9905 0.5761 0.038 Uiso 1 1 calc R . . C8 C -0.0026(3) 0.9079(2) 0.61035(17) 0.0285(5) Uani 1 1 d . . . H8 H 0.0869 1.0087 0.6219 0.034 Uiso 1 1 calc R . . C9 C 0.2246(2) 0.7809(2) 0.63657(16) 0.0221(5) Uani 1 1 d . . . C11 C 0.2342(2) 0.6332(2) 0.67762(16) 0.0226(5) Uani 1 1 d . . . C12 C 0.0914(2) 0.4961(2) 0.66342(16) 0.0242(5) Uani 1 1 d . . . C13 C -0.0967(3) 0.6306(2) 0.60723(17) 0.0244(5) Uani 1 1 d . . . C14 C 0.0395(2) 0.7741(2) 0.62114(16) 0.0227(5) Uani 1 1 d . . . C15 C 0.3472(2) 0.9318(2) 0.70785(17) 0.0216(5) Uani 1 1 d . . . C16 C 0.3257(3) 0.9615(2) 0.81375(17) 0.0275(5) Uani 1 1 d . . . H16 H 0.2327 0.8886 0.8397 0.033 Uiso 1 1 calc R . . C17 C 0.4359(3) 1.0946(2) 0.88290(18) 0.0302(6) Uani 1 1 d . . . H17 H 0.4189 1.1124 0.9553 0.036 Uiso 1 1 calc R . . C18 C 0.5715(3) 1.2014(2) 0.84491(18) 0.0278(5) Uani 1 1 d . . . C19 C 0.5938(3) 1.1750(2) 0.73914(18) 0.0289(5) Uani 1 1 d . . . H19 H 0.6854 1.2490 0.7129 0.035 Uiso 1 1 calc R . . C20 C 0.4829(2) 1.0409(2) 0.67130(17) 0.0261(5) Uani 1 1 d . . . H20 H 0.4998 1.0234 0.5989 0.031 Uiso 1 1 calc R . . C21 C 0.6648(4) 1.3721(3) 1.0137(2) 0.0534(8) Uani 1 1 d . . . H21A H 0.5520 1.3823 1.0145 0.080 Uiso 1 1 calc R . . H21B H 0.7556 1.4714 1.0484 0.080 Uiso 1 1 calc R . . H21C H 0.6707 1.2861 1.0527 0.080 Uiso 1 1 calc R . . Cl1G Cl 0.1354(5) 1.2709(4) 0.1019(3) 0.0784(9) Uani 0.50 1 d P . . C1G C 0.107(2) 1.2162(15) 0.0791(16) 0.125(7) Uani 0.50 1 d P . . C2G C 0.0691(3) 0.9512(5) 0.0705(3) 0.0619(9) Uani 1 1 d . . . C3G C 0.0434(7) 1.0792(7) 0.0347(5) 0.0469(13) Uiso 0.50 1 d P . . C4G C 0.1416(7) 1.0993(11) 0.1214(5) 0.070(2) Uani 0.50 1 d P . . C5G C -0.0029(9) 1.1937(10) -0.0256(7) 0.081(2) Uani 0.50 1 d P . . 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 O9 0.0254(8) 0.0258(8) 0.0251(9) 0.0022(7) 0.0056(6) 0.0069(7) O10 0.0228(8) 0.0219(8) 0.0404(10) 0.0030(7) -0.0026(7) 0.0069(6) O11 0.0446(10) 0.0310(9) 0.0348(10) -0.0035(7) -0.0049(8) 0.0031(8) C1 0.0239(12) 0.0260(12) 0.0305(13) 0.0017(10) 0.0017(9) 0.0069(10) C2 0.0298(13) 0.0327(14) 0.0377(15) 0.0051(11) -0.0001(10) 0.0168(11) C3 0.0379(14) 0.0244(13) 0.0398(15) 0.0069(11) 0.0053(11) 0.0149(11) C4 0.0300(13) 0.0231(12) 0.0360(14) 0.0047(10) 0.0040(10) 0.0087(10) C5 0.0209(12) 0.0294(13) 0.0349(14) 0.0033(10) 0.0038(10) 0.0067(10) C6 0.0243(12) 0.0378(14) 0.0324(14) 0.0035(11) 0.0024(10) 0.0152(11) C7 0.0300(13) 0.0308(13) 0.0372(15) 0.0059(11) 0.0058(10) 0.0156(11) C8 0.0258(12) 0.0253(12) 0.0342(14) 0.0047(10) 0.0038(10) 0.0090(10) C9 0.0223(11) 0.0243(12) 0.0213(12) 0.0047(9) 0.0050(9) 0.0096(9) C11 0.0226(11) 0.0225(11) 0.0224(12) 0.0015(9) 0.0040(9) 0.0084(9) C12 0.0190(11) 0.0278(12) 0.0256(13) 0.0016(10) 0.0009(9) 0.0099(10) C13 0.0270(12) 0.0235(12) 0.0249(13) 0.0025(9) 0.0050(9) 0.0120(10) C14 0.0209(11) 0.0236(12) 0.0228(12) 0.0006(9) 0.0021(9) 0.0080(9) C15 0.0202(11) 0.0216(11) 0.0255(13) 0.0042(9) 0.0019(9) 0.0108(9) C16 0.0294(12) 0.0248(12) 0.0280(14) 0.0071(10) 0.0056(10) 0.0083(10) C17 0.0401(14) 0.0280(13) 0.0239(13) 0.0039(10) 0.0030(10) 0.0147(11) C18 0.0272(13) 0.0215(12) 0.0309(14) 0.0010(10) -0.0055(10) 0.0080(10) C19 0.0229(12) 0.0266(13) 0.0341(14) 0.0049(10) 0.0039(10) 0.0052(10) C20 0.0238(12) 0.0281(12) 0.0272(13) 0.0027(10) 0.0051(9) 0.0104(10) C21 0.0750(19) 0.0397(15) 0.0319(16) -0.0049(12) -0.0053(13) 0.0106(14) Cl1G 0.0703(14) 0.062(2) 0.0778(16) -0.0014(15) 0.0172(11) -0.0062(15) C1G 0.115(12) 0.038(8) 0.191(16) -0.034(8) 0.112(11) -0.024(7) C2G 0.0346(17) 0.083(2) 0.066(2) 0.0275(19) 0.0144(14) 0.0108(17) C4G 0.036(3) 0.099(6) 0.048(4) -0.002(4) 0.011(3) -0.007(4) C5G 0.061(5) 0.078(6) 0.112(7) 0.021(5) 0.046(4) 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 O9 C9 1.460(2) . ? O9 H9 0.966(2) . ? O10 C13 1.393(2) . ? O10 C12 1.394(2) . ? O11 C18 1.374(2) . ? O11 C21 1.430(3) . ? C1 C2 1.376(3) . ? C1 C11 1.399(3) . ? C1 H1 0.9500 . ? C2 C3 1.386(3) . ? C2 H2 0.9500 . ? C3 C4 1.372(3) . ? C3 H3 0.9500 . ? C4 C12 1.385(3) . ? C4 H4 0.9500 . ? C5 C6 1.377(3) . ? C5 C13 1.384(3) . ? C5 H5 0.9500 . ? C6 C7 1.387(3) . ? C6 H6 0.9500 . ? C7 C8 1.381(3) . ? C7 H7 0.9500 . ? C8 C14 1.393(3) . ? C8 H8 0.9500 . ? C9 C11 1.514(3) . ? C9 C14 1.517(3) . ? C9 C15 1.526(3) . ? C11 C12 1.379(3) . ? C13 C14 1.387(3) . ? C15 C16 1.386(3) . ? C15 C20 1.390(3) . ? C16 C17 1.387(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C17 H17 0.9500 . ? C18 C19 1.382(3) . ? C19 C20 1.386(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? Cl1G C1G 0.513(12) . ? Cl1G C4G 1.623(10) . ? Cl1G C3G 1.730(6) . ? Cl1G C5G 1.798(10) . ? C1G C3G 1.221(12) . ? C1G C4G 1.34(2) . ? C1G C5G 1.48(2) . ? C2G C5G 1.283(8) 2_575 ? C2G C4G 1.333(8) . ? C2G C3G 1.367(6) . ? C2G C3G 1.484(6) 2_575 ? C3G C4G 1.253(8) . ? C3G C5G 1.480(10) . ? C3G C2G 1.484(6) 2_575 ? C3G C3G 1.503(11) 2_575 ? C5G C2G 1.283(8) 2_575 ? 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 C9 O9 H9 107.2(17) . . ? C13 O10 C12 118.33(15) . . ? C18 O11 C21 116.98(18) . . ? C2 C1 C11 121.63(19) . . ? C2 C1 H1 119.2 . . ? C11 C1 H1 119.2 . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C12 119.40(19) . . ? C3 C4 H4 120.3 . . ? C12 C4 H4 120.3 . . ? C6 C5 C13 119.08(19) . . ? C6 C5 H5 120.5 . . ? C13 C5 H5 120.5 . . ? C5 C6 C7 120.04(19) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 119.8(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C14 121.71(19) . . ? C7 C8 H8 119.1 . . ? C14 C8 H8 119.1 . . ? O9 C9 C11 108.35(16) . . ? O9 C9 C14 107.83(15) . . ? C11 C9 C14 109.95(16) . . ? O9 C9 C15 105.57(15) . . ? C11 C9 C15 112.32(16) . . ? C14 C9 C15 112.56(16) . . ? C12 C11 C1 116.61(19) . . ? C12 C11 C9 121.36(17) . . ? C1 C11 C9 121.85(17) . . ? C11 C12 C4 122.62(19) . . ? C11 C12 O10 122.08(18) . . ? C4 C12 O10 115.29(17) . . ? C5 C13 C14 122.64(19) . . ? C5 C13 O10 115.30(17) . . ? C14 C13 O10 122.05(18) . . ? C13 C14 C8 116.71(18) . . ? C13 C14 C9 120.88(18) . . ? C8 C14 C9 122.15(17) . . ? C16 C15 C20 118.05(19) . . ? C16 C15 C9 119.42(18) . . ? C20 C15 C9 122.52(19) . . ? C15 C16 C17 121.9(2) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C16 C17 C18 119.1(2) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? O11 C18 C19 115.51(18) . . ? O11 C18 C17 124.6(2) . . ? C19 C18 C17 119.93(19) . . ? C18 C19 C20 120.2(2) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 120.8(2) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? O11 C21 H21A 109.5 . . ? O11 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O11 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1G Cl1G C4G 49(3) . . ? C1G Cl1G C3G 5(3) . . ? C4G Cl1G C3G 43.7(3) . . ? C1G Cl1G C5G 45(3) . . ? C4G Cl1G C5G 93.2(4) . . ? C3G Cl1G C5G 49.6(3) . . ? Cl1G C1G C3G 173(4) . . ? Cl1G C1G C4G 115(4) . . ? C3G C1G C4G 58.3(8) . . ? Cl1G C1G C5G 121(3) . . ? C3G C1G C5G 65.7(9) . . ? C4G C1G C5G 124.0(8) . . ? C5G C2G C4G 177.1(6) 2_575 . ? C5G C2G C3G 127.6(5) 2_575 . ? C4G C2G C3G 55.3(4) . . ? C5G C2G C3G 64.2(4) 2_575 2_575 ? C4G C2G C3G 118.7(5) . 2_575 ? C3G C2G C3G 63.5(4) . 2_575 ? C1G C3G C4G 65.6(11) . . ? C1G C3G C2G 126.6(13) . . ? C4G C3G C2G 61.0(5) . . ? C1G C3G C5G 65.5(11) . . ? C4G C3G C5G 131.1(7) . . ? C2G C3G C5G 167.7(6) . . ? C1G C3G C2G 116.9(13) . 2_575 ? C4G C3G C2G 176.8(7) . 2_575 ? C2G C3G C2G 116.5(4) . 2_575 ? C5G C3G C2G 51.3(4) . 2_575 ? C1G C3G C3G 171.2(14) . 2_575 ? C4G C3G C3G 123.0(8) . 2_575 ? C2G C3G C3G 62.1(4) . 2_575 ? C5G C3G C3G 105.7(7) . 2_575 ? C2G C3G C3G 54.5(4) 2_575 2_575 ? C1G C3G Cl1G 2.1(12) . . ? C4G C3G Cl1G 63.6(5) . . ? C2G C3G Cl1G 124.6(4) . . ? C5G C3G Cl1G 67.6(5) . . ? C2G C3G Cl1G 118.9(4) 2_575 . ? C3G C3G Cl1G 173.3(6) 2_575 . ? C3G C4G C2G 63.8(4) . . ? C3G C4G C1G 56.0(8) . . ? C2G C4G C1G 119.8(9) . . ? C3G C4G Cl1G 72.7(5) . . ? C2G C4G Cl1G 136.4(5) . . ? C1G C4G Cl1G 16.7(7) . . ? C2G C5G C1G 113.3(8) 2_575 . ? C2G C5G C3G 64.5(4) 2_575 . ? C1G C5G C3G 48.7(6) . . ? C2G C5G Cl1G 127.3(6) 2_575 . ? C1G C5G Cl1G 14.1(7) . . ? C3G C5G Cl1G 62.8(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 C11 C1 C2 C3 -1.6(3) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C12 0.5(3) . . . . ? C13 C5 C6 C7 -1.4(3) . . . . ? C5 C6 C7 C8 1.6(3) . . . . ? C6 C7 C8 C14 0.3(3) . . . . ? C2 C1 C11 C12 1.9(3) . . . . ? C2 C1 C11 C9 -173.1(2) . . . . ? O9 C9 C11 C12 -96.2(2) . . . . ? C14 C9 C11 C12 21.5(3) . . . . ? C15 C9 C11 C12 147.62(19) . . . . ? O9 C9 C11 C1 78.7(2) . . . . ? C14 C9 C11 C1 -163.71(18) . . . . ? C15 C9 C11 C1 -37.5(3) . . . . ? C1 C11 C12 C4 -1.1(3) . . . . ? C9 C11 C12 C4 173.96(19) . . . . ? C1 C11 C12 O10 -179.85(18) . . . . ? C9 C11 C12 O10 -4.8(3) . . . . ? C3 C4 C12 C11 -0.1(3) . . . . ? C3 C4 C12 O10 178.72(18) . . . . ? C13 O10 C12 C11 -13.5(3) . . . . ? C13 O10 C12 C4 167.74(18) . . . . ? C6 C5 C13 C14 -0.7(3) . . . . ? C6 C5 C13 O10 -179.50(18) . . . . ? C12 O10 C13 C5 -168.89(18) . . . . ? C12 O10 C13 C14 12.3(3) . . . . ? C5 C13 C14 C8 2.5(3) . . . . ? O10 C13 C14 C8 -178.82(19) . . . . ? C5 C13 C14 C9 -171.82(19) . . . . ? O10 C13 C14 C9 6.9(3) . . . . ? C7 C8 C14 C13 -2.3(3) . . . . ? C7 C8 C14 C9 171.97(19) . . . . ? O9 C9 C14 C13 95.5(2) . . . . ? C11 C9 C14 C13 -22.4(3) . . . . ? C15 C9 C14 C13 -148.45(19) . . . . ? O9 C9 C14 C8 -78.5(2) . . . . ? C11 C9 C14 C8 163.59(19) . . . . ? C15 C9 C14 C8 37.6(3) . . . . ? O9 C9 C15 C16 179.90(17) . . . . ? C11 C9 C15 C16 -62.2(2) . . . . ? C14 C9 C15 C16 62.5(2) . . . . ? O9 C9 C15 C20 -1.1(2) . . . . ? C11 C9 C15 C20 116.8(2) . . . . ? C14 C9 C15 C20 -118.5(2) . . . . ? C20 C15 C16 C17 -0.7(3) . . . . ? C9 C15 C16 C17 178.32(19) . . . . ? C15 C16 C17 C18 0.2(3) . . . . ? C21 O11 C18 C19 177.6(2) . . . . ? C21 O11 C18 C17 -1.1(3) . . . . ? C16 C17 C18 O11 179.3(2) . . . . ? C16 C17 C18 C19 0.7(3) . . . . ? O11 C18 C19 C20 -179.80(18) . . . . ? C17 C18 C19 C20 -1.1(3) . . . . ? C18 C19 C20 C15 0.5(3) . . . . ? C16 C15 C20 C19 0.4(3) . . . . ? C9 C15 C20 C19 -178.64(19) . . . . ? C4G Cl1G C1G C3G 14(23) . . . . ? C5G Cl1G C1G C3G -167(27) . . . . ? C3G Cl1G C1G C4G -14(23) . . . . ? C5G Cl1G C1G C4G 179(4) . . . . ? C4G Cl1G C1G C5G -179(4) . . . . ? C3G Cl1G C1G C5G 167(27) . . . . ? Cl1G C1G C3G C4G -15(24) . . . . ? C5G C1G C3G C4G 177.4(9) . . . . ? Cl1G C1G C3G C2G -14(25) . . . . ? C4G C1G C3G C2G 0.3(10) . . . . ? C5G C1G C3G C2G 177.7(7) . . . . ? Cl1G C1G C3G C5G 168(25) . . . . ? C4G C1G C3G C5G -177.4(9) . . . . ? Cl1G C1G C3G C2G 167(24) . . . 2_575 ? C4G C1G C3G C2G -177.8(6) . . . 2_575 ? C5G C1G C3G C2G -0.4(8) . . . 2_575 ? Cl1G C1G C3G C3G 176(20) . . . 2_575 ? C4G C1G C3G C3G -169(6) . . . 2_575 ? C5G C1G C3G C3G 9(7) . . . 2_575 ? C4G C1G C3G Cl1G 15(24) . . . . ? C5G C1G C3G Cl1G -168(25) . . . . ? C5G C2G C3G C1G 179.4(11) 2_575 . . . ? C4G C2G C3G C1G -0.3(11) . . . . ? C3G C2G C3G C1G -178.1(12) 2_575 . . . ? C5G C2G C3G C4G 179.7(6) 2_575 . . . ? C3G C2G C3G C4G -177.8(6) 2_575 . . . ? C5G C2G C3G C5G -10(3) 2_575 . . . ? C4G C2G C3G C5G 170(2) . . . . ? C3G C2G C3G C5G -8(2) 2_575 . . . ? C5G C2G C3G C2G -2.5(7) 2_575 . . 2_575 ? C4G C2G C3G C2G 177.8(6) . . . 2_575 ? C3G C2G C3G C2G 0.0 2_575 . . 2_575 ? C5G C2G C3G C3G -2.5(7) 2_575 . . 2_575 ? C4G C2G C3G C3G 177.8(6) . . . 2_575 ? C5G C2G C3G Cl1G 178.8(5) 2_575 . . . ? C4G C2G C3G Cl1G -1.0(4) . . . . ? C3G C2G C3G Cl1G -178.8(7) 2_575 . . . ? C4G Cl1G C3G C1G -165(25) . . . . ? C5G Cl1G C3G C1G 12(25) . . . . ? C1G Cl1G C3G C4G 165(25) . . . . ? C5G Cl1G C3G C4G 176.9(5) . . . . ? C1G Cl1G C3G C2G 166(25) . . . . ? C4G Cl1G C3G C2G 0.9(4) . . . . ? C5G Cl1G C3G C2G 177.9(6) . . . . ? C1G Cl1G C3G C5G -12(25) . . . . ? C4G Cl1G C3G C5G -176.9(5) . . . . ? C1G Cl1G C3G C2G -13(25) . . . 2_575 ? C4G Cl1G C3G C2G -177.8(6) . . . 2_575 ? C5G Cl1G C3G C2G -0.9(4) . . . 2_575 ? C1G Cl1G C3G C3G -5(26) . . . 2_575 ? C4G Cl1G C3G C3G -170(5) . . . 2_575 ? C5G Cl1G C3G C3G 7(5) . . . 2_575 ? C1G C3G C4G C2G 179.7(9) . . . . ? C5G C3G C4G C2G -177.1(7) . . . . ? C2G C3G C4G C2G -38(11) 2_575 . . . ? C3G C3G C4G C2G -2.3(7) 2_575 . . . ? Cl1G C3G C4G C2G 179.1(4) . . . . ? C2G C3G C4G C1G -179.7(9) . . . . ? C5G C3G C4G C1G 3.2(11) . . . . ? C2G C3G C4G C1G 142(11) 2_575 . . . ? C3G C3G C4G C1G 178.0(11) 2_575 . . . ? Cl1G C3G C4G C1G -0.6(10) . . . . ? C1G C3G C4G Cl1G 0.6(10) . . . . ? C2G C3G C4G Cl1G -179.1(4) . . . . ? C5G C3G C4G Cl1G 3.8(7) . . . . ? C2G C3G C4G Cl1G 143(11) 2_575 . . . ? C3G C3G C4G Cl1G 178.6(7) 2_575 . . . ? C5G C2G C4G C3G -176(10) 2_575 . . . ? C3G C2G C4G C3G 2.2(6) 2_575 . . . ? C5G C2G C4G C1G -175(10) 2_575 . . . ? C3G C2G C4G C1G 0.3(9) . . . . ? C3G C2G C4G C1G 2.5(11) 2_575 . . . ? C5G C2G C4G Cl1G -175(9) 2_575 . . . ? C3G C2G C4G Cl1G 1.2(5) . . . . ? C3G C2G C4G Cl1G 3.5(9) 2_575 . . . ? Cl1G C1G C4G C3G 178(3) . . . . ? C5G C1G C4G C3G -2.9(10) . . . . ? Cl1G C1G C4G C2G 178(2) . . . . ? C3G C1G C4G C2G -0.3(10) . . . . ? C5G C1G C4G C2G -3.2(18) . . . . ? C3G C1G C4G Cl1G -178(3) . . . . ? C5G C1G C4G Cl1G 179(4) . . . . ? C1G Cl1G C4G C3G -2(3) . . . . ? C5G Cl1G C4G C3G -2.3(4) . . . . ? C1G Cl1G C4G C2G -3(3) . . . . ? C3G Cl1G C4G C2G -1.2(5) . . . . ? C5G Cl1G C4G C2G -3.5(7) . . . . ? C3G Cl1G C4G C1G 2(3) . . . . ? C5G Cl1G C4G C1G -1(3) . . . . ? Cl1G C1G C5G C2G -178(3) . . . 2_575 ? C3G C1G C5G C2G 0.5(9) . . . 2_575 ? C4G C1G C5G C2G 3.2(17) . . . 2_575 ? Cl1G C1G C5G C3G -178(3) . . . . ? C4G C1G C5G C3G 2.7(9) . . . . ? C3G C1G C5G Cl1G 178(3) . . . . ? C4G C1G C5G Cl1G -179(4) . . . . ? C1G C3G C5G C2G -179.5(9) . . . 2_575 ? C4G C3G C5G C2G 177.3(8) . . . 2_575 ? C2G C3G C5G C2G 9(2) . . . 2_575 ? C3G C3G C5G C2G 1.8(5) 2_575 . . 2_575 ? Cl1G C3G C5G C2G -179.0(4) . . . 2_575 ? C4G C3G C5G C1G -3.2(11) . . . . ? C2G C3G C5G C1G -171(3) . . . . ? C2G C3G C5G C1G 179.5(9) 2_575 . . . ? C3G C3G C5G C1G -178.6(11) 2_575 . . . ? Cl1G C3G C5G C1G 0.5(10) . . . . ? C1G C3G C5G Cl1G -0.5(10) . . . . ? C4G C3G C5G Cl1G -3.6(7) . . . . ? C2G C3G C5G Cl1G -172(2) . . . . ? C2G C3G C5G Cl1G 179.0(4) 2_575 . . . ? C3G C3G C5G Cl1G -179.1(6) 2_575 . . . ? C1G Cl1G C5G C2G 3(3) . . . 2_575 ? C4G Cl1G C5G C2G 3.2(6) . . . 2_575 ? C3G Cl1G C5G C2G 1.1(5) . . . 2_575 ? C4G Cl1G C5G C1G 1(3) . . . . ? C3G Cl1G C5G C1G -1(3) . . . . ? C1G Cl1G C5G C3G 1(3) . . . . ? C4G Cl1G C5G C3G 2.1(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 O9 H9 O10 0.966(2) 1.910(4) 2.8703(19) 173(2) 2_566 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.234 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 934127' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 O3.C3.09 H2.78 Cl0.41' _chemical_formula_sum 'C23.09 H18.78 Cl0.41 O3' _chemical_formula_weight 358.66 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3704(3) _cell_length_b 9.0991(4) _cell_length_c 12.6749(6) _cell_angle_alpha 95.811(1) _cell_angle_beta 96.459(1) _cell_angle_gamma 110.021(3) _cell_volume 891.11(7) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 11944 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 25.09 _exptl_crystal_description block _exptl_crystal_colour colourles _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9480 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11944 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0848 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 25.09 _reflns_number_total 3107 _reflns_number_gt 1802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0624P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 3107 _refine_ls_number_parameters 268 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O9 O 0.28157(19) 0.78618(19) 0.53197(13) 0.0270(4) Uani 1 1 d D . . H9 H 0.212(3) 0.692(2) 0.4823(19) 0.078(10) Uiso 1 1 d D . . O10 O -0.07113(18) 0.48901(18) 0.61776(13) 0.0307(5) Uani 1 1 d . . . O11 O 0.6874(2) 1.3377(2) 0.90488(15) 0.0417(5) Uani 1 1 d . . . C1 C 0.3898(3) 0.6244(3) 0.7237(2) 0.0292(6) Uani 1 1 d . . . H1 H 0.4905 0.7170 0.7371 0.035 Uiso 1 1 calc R . . C2 C 0.4008(3) 0.4848(3) 0.7503(2) 0.0330(7) Uani 1 1 d . . . H2 H 0.5088 0.4811 0.7793 0.040 Uiso 1 1 calc R . . C3 C 0.2547(3) 0.3502(3) 0.7346(2) 0.0340(7) Uani 1 1 d . . . H3 H 0.2619 0.2541 0.7538 0.041 Uiso 1 1 calc R . . C4 C 0.0993(3) 0.3551(3) 0.6913(2) 0.0312(6) Uani 1 1 d . . . H4 H -0.0018 0.2629 0.6805 0.037 Uiso 1 1 calc R . . C5 C -0.2668(3) 0.6165(3) 0.5797(2) 0.0301(6) Uani 1 1 d . . . H5 H -0.3569 0.5161 0.5701 0.036 Uiso 1 1 calc R . . C6 C -0.3034(3) 0.7509(3) 0.5668(2) 0.0314(6) Uani 1 1 d . . . H6 H -0.4190 0.7434 0.5468 0.038 Uiso 1 1 calc R . . C7 C -0.1707(3) 0.8972(3) 0.5831(2) 0.0322(6) Uani 1 1 d . . . H7 H -0.1955 0.9903 0.5757 0.039 Uiso 1 1 calc R . . C8 C -0.0031(3) 0.9067(3) 0.6101(2) 0.0299(6) Uani 1 1 d . . . H8 H 0.0864 1.0076 0.6215 0.036 Uiso 1 1 calc R . . C9 C 0.2245(3) 0.7813(3) 0.63638(18) 0.0234(6) Uani 1 1 d . . . C11 C 0.2340(3) 0.6335(3) 0.67763(19) 0.0237(6) Uani 1 1 d . . . C12 C 0.0916(3) 0.4958(3) 0.66353(19) 0.0261(6) Uani 1 1 d . . . C13 C -0.0962(3) 0.6299(3) 0.60688(19) 0.0260(6) Uani 1 1 d . . . C14 C 0.0393(3) 0.7743(3) 0.62113(18) 0.0229(6) Uani 1 1 d . . . C15 C 0.3464(3) 0.9318(3) 0.7077(2) 0.0236(6) Uani 1 1 d . . . C16 C 0.3247(3) 0.9615(3) 0.8135(2) 0.0301(6) Uani 1 1 d . . . H16 H 0.2314 0.8886 0.8391 0.036 Uiso 1 1 calc R . . C17 C 0.4350(3) 1.0944(3) 0.8833(2) 0.0310(6) Uani 1 1 d . . . H17 H 0.4180 1.1119 0.9556 0.037 Uiso 1 1 calc R . . C18 C 0.5707(3) 1.2012(3) 0.8450(2) 0.0294(6) Uani 1 1 d . . . C19 C 0.5941(3) 1.1755(3) 0.7392(2) 0.0295(6) Uani 1 1 d . . . H19 H 0.6862 1.2496 0.7133 0.035 Uiso 1 1 calc R . . C20 C 0.4829(3) 1.0411(3) 0.6710(2) 0.0277(6) Uani 1 1 d . . . H20 H 0.4999 1.0237 0.5986 0.033 Uiso 1 1 calc R . . C21 C 0.6637(4) 1.3717(3) 1.0135(2) 0.0535(8) Uani 1 1 d . . . H21A H 0.6686 1.2851 1.0523 0.080 Uiso 1 1 calc R . . H21B H 0.5514 1.3827 1.0142 0.080 Uiso 1 1 calc R . . H21C H 0.7550 1.4705 1.0483 0.080 Uiso 1 1 calc R . . Cl1G Cl -0.1369(8) 0.7288(7) -0.1014(5) 0.0816(14) Uani 0.40 1 d P . . C1G C -0.116(2) 0.7824(19) -0.0899(18) 0.131(8) Uani 0.60 1 d P . . C2G C 0.0688(4) 0.9499(6) 0.0691(3) 0.0655(10) Uani 1 1 d . . . C3G C -0.0441(7) 0.9208(9) -0.0351(6) 0.0546(18) Uani 0.50 1 d P . . C4G C 0.0001(12) 0.8038(12) 0.0213(10) 0.085(3) Uani 0.50 1 d P . . C5G C -0.1434(10) 0.9041(13) -0.1227(7) 0.079(3) Uani 0.50 1 d P . . 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 O9 0.0280(9) 0.0275(10) 0.0247(10) 0.0027(8) 0.0056(7) 0.0088(8) O10 0.0239(9) 0.0243(10) 0.0416(11) 0.0033(8) -0.0023(8) 0.0085(7) O11 0.0482(12) 0.0303(11) 0.0346(12) -0.0032(9) -0.0037(9) 0.0045(9) C1 0.0247(14) 0.0265(15) 0.0349(16) 0.0028(12) 0.0047(11) 0.0077(11) C2 0.0329(15) 0.0341(16) 0.0364(17) 0.0060(13) -0.0007(12) 0.0192(13) C3 0.0408(16) 0.0261(15) 0.0391(17) 0.0081(13) 0.0040(13) 0.0165(13) C4 0.0307(15) 0.0256(15) 0.0352(17) 0.0053(12) 0.0028(12) 0.0082(12) C5 0.0253(14) 0.0303(15) 0.0332(17) 0.0026(12) 0.0038(11) 0.0088(12) C6 0.0268(14) 0.0372(16) 0.0337(16) 0.0042(13) 0.0036(11) 0.0167(13) C7 0.0320(15) 0.0291(15) 0.0400(17) 0.0062(13) 0.0049(12) 0.0165(13) C8 0.0255(14) 0.0269(15) 0.0347(16) 0.0028(12) 0.0032(11) 0.0070(11) C9 0.0233(13) 0.0245(14) 0.0224(14) 0.0037(11) 0.0044(10) 0.0086(11) C11 0.0233(13) 0.0245(14) 0.0236(15) 0.0020(11) 0.0037(10) 0.0091(11) C12 0.0233(13) 0.0292(15) 0.0259(15) 0.0021(12) 0.0014(11) 0.0107(11) C13 0.0301(14) 0.0255(15) 0.0266(15) 0.0042(11) 0.0057(11) 0.0149(12) C14 0.0236(13) 0.0215(14) 0.0234(15) 0.0027(11) 0.0012(10) 0.0087(11) C15 0.0217(13) 0.0219(13) 0.0293(16) 0.0045(11) 0.0025(10) 0.0109(11) C16 0.0302(14) 0.0270(15) 0.0341(17) 0.0086(12) 0.0080(12) 0.0094(12) C17 0.0381(15) 0.0302(15) 0.0252(16) 0.0042(12) 0.0044(12) 0.0130(13) C18 0.0311(15) 0.0243(15) 0.0303(17) 0.0007(12) -0.0059(12) 0.0108(12) C19 0.0254(14) 0.0269(15) 0.0345(17) 0.0060(12) 0.0034(11) 0.0071(11) C20 0.0257(14) 0.0301(15) 0.0287(16) 0.0052(12) 0.0049(11) 0.0116(12) C21 0.071(2) 0.0420(18) 0.0330(19) -0.0053(14) -0.0057(15) 0.0096(16) Cl1G 0.074(2) 0.062(4) 0.083(2) 0.003(2) 0.0162(17) -0.007(2) C1G 0.096(9) 0.056(12) 0.198(15) -0.038(9) 0.106(10) -0.037(8) C2G 0.043(2) 0.087(3) 0.072(3) 0.037(3) 0.0194(19) 0.019(2) C3G 0.024(4) 0.075(6) 0.052(5) 0.015(4) 0.010(3) 0.001(3) C4G 0.069(6) 0.069(6) 0.136(9) 0.035(7) 0.054(6) 0.030(5) C5G 0.049(5) 0.087(8) 0.063(6) -0.010(5) 0.017(4) -0.020(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 O9 C9 1.456(3) . ? O9 H9 0.966(2) . ? O10 C13 1.386(3) . ? O10 C12 1.397(3) . ? O11 C18 1.373(3) . ? O11 C21 1.430(3) . ? C1 C2 1.376(3) . ? C1 C11 1.400(3) . ? C1 H1 0.9500 . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C3 C4 1.372(3) . ? C3 H3 0.9500 . ? C4 C12 1.383(3) . ? C4 H4 0.9500 . ? C5 C6 1.379(3) . ? C5 C13 1.391(3) . ? C5 H5 0.9500 . ? C6 C7 1.389(3) . ? C6 H6 0.9500 . ? C7 C8 1.377(3) . ? C7 H7 0.9500 . ? C8 C14 1.383(3) . ? C8 H8 0.9500 . ? C9 C11 1.515(3) . ? C9 C14 1.519(3) . ? C9 C15 1.523(3) . ? C11 C12 1.380(3) . ? C13 C14 1.390(3) . ? C15 C16 1.385(3) . ? C15 C20 1.395(3) . ? C16 C17 1.390(3) . ? C16 H16 0.9500 . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 C19 1.384(3) . ? C19 C20 1.391(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? Cl1G C5G 1.662(13) . ? Cl1G C3G 1.729(9) . ? Cl1G C4G 1.745(15) . ? C1G C3G 1.280(17) . ? C1G C5G 1.30(2) . ? C1G C4G 1.57(2) . ? C2G C4G 1.304(10) . ? C2G C5G 1.331(10) 2_575 ? C2G C3G 1.365(8) 2_575 ? C2G C3G 1.478(8) . ? C3G C5G 1.272(10) . ? C3G C2G 1.365(8) 2_575 ? C3G C4G 1.465(12) . ? C3G C3G 1.510(15) 2_575 ? C5G C2G 1.331(9) 2_575 ? 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 C9 O9 H9 110.9(19) . . ? C13 O10 C12 118.34(17) . . ? C18 O11 C21 116.8(2) . . ? C2 C1 C11 121.7(2) . . ? C2 C1 H1 119.1 . . ? C11 C1 H1 119.1 . . ? C1 C2 C3 119.9(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C12 119.1(2) . . ? C3 C4 H4 120.4 . . ? C12 C4 H4 120.4 . . ? C6 C5 C13 119.1(2) . . ? C6 C5 H5 120.5 . . ? C13 C5 H5 120.5 . . ? C5 C6 C7 119.9(2) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 119.7(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C14 122.2(2) . . ? C7 C8 H8 118.9 . . ? C14 C8 H8 118.9 . . ? O9 C9 C11 108.35(18) . . ? O9 C9 C14 107.94(18) . . ? C11 C9 C14 109.84(17) . . ? O9 C9 C15 105.83(17) . . ? C11 C9 C15 112.23(19) . . ? C14 C9 C15 112.41(19) . . ? C12 C11 C1 116.2(2) . . ? C12 C11 C9 121.6(2) . . ? C1 C11 C9 122.0(2) . . ? C11 C12 C4 123.0(2) . . ? C11 C12 O10 121.8(2) . . ? C4 C12 O10 115.2(2) . . ? O10 C13 C14 122.5(2) . . ? O10 C13 C5 115.2(2) . . ? C14 C13 C5 122.3(2) . . ? C8 C14 C13 116.9(2) . . ? C8 C14 C9 122.3(2) . . ? C13 C14 C9 120.5(2) . . ? C16 C15 C20 118.1(2) . . ? C16 C15 C9 119.6(2) . . ? C20 C15 C9 122.3(2) . . ? C15 C16 C17 122.2(2) . . ? C15 C16 H16 118.9 . . ? C17 C16 H16 118.9 . . ? C16 C17 C18 118.7(2) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? O11 C18 C19 115.1(2) . . ? O11 C18 C17 124.5(2) . . ? C19 C18 C17 120.4(2) . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C15 120.7(2) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? O11 C21 H21A 109.5 . . ? O11 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O11 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C5G Cl1G C3G 44.0(4) . . ? C5G Cl1G C4G 93.9(6) . . ? C3G Cl1G C4G 49.9(4) . . ? C3G C1G C5G 59.0(9) . . ? C3G C1G C4G 60.8(9) . . ? C5G C1G C4G 119.7(11) . . ? C4G C2G C5G 176.6(7) . 2_575 ? C4G C2G C3G 127.1(6) . 2_575 ? C5G C2G C3G 56.3(5) 2_575 2_575 ? C4G C2G C3G 63.2(5) . . ? C5G C2G C3G 120.3(7) 2_575 . ? C3G C2G C3G 64.0(6) 2_575 . ? C5G C3G C1G 61.4(13) . . ? C5G C3G C2G 60.5(6) . 2_575 ? C1G C3G C2G 121.8(14) . 2_575 ? C5G C3G C4G 130.8(9) . . ? C1G C3G C4G 69.5(12) . . ? C2G C3G C4G 168.5(8) 2_575 . ? C5G C3G C2G 176.1(9) . . ? C1G C3G C2G 122.1(14) . . ? C2G C3G C2G 116.0(6) 2_575 . ? C4G C3G C2G 52.6(5) . . ? C5G C3G C3G 122.1(11) . 2_575 ? C1G C3G C3G 176.4(16) . 2_575 ? C2G C3G C3G 61.7(6) 2_575 2_575 ? C4G C3G C3G 106.9(9) . 2_575 ? C2G C3G C3G 54.4(5) . 2_575 ? C5G C3G Cl1G 65.2(6) . . ? C1G C3G Cl1G 4.0(13) . . ? C2G C3G Cl1G 125.7(5) 2_575 . ? C4G C3G Cl1G 65.7(7) . . ? C2G C3G Cl1G 118.3(6) . . ? C3G C3G Cl1G 172.5(8) 2_575 . ? C2G C4G C3G 64.2(5) . . ? C2G C4G C1G 113.9(9) . . ? C3G C4G C1G 49.7(8) . . ? C2G C4G Cl1G 128.7(7) . . ? C3G C4G Cl1G 64.5(6) . . ? C1G C4G Cl1G 14.8(8) . . ? C3G C5G C1G 59.6(11) . . ? C3G C5G C2G 63.2(6) . 2_575 ? C1G C5G C2G 122.8(12) . 2_575 ? C3G C5G Cl1G 70.8(7) . . ? C1G C5G Cl1G 11.2(10) . . ? C2G C5G Cl1G 134.0(7) 2_575 . ? 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 C11 C1 C2 C3 -2.0(4) . . . . ? C1 C2 C3 C4 0.9(4) . . . . ? C2 C3 C4 C12 0.2(4) . . . . ? C13 C5 C6 C7 -1.3(4) . . . . ? C5 C6 C7 C8 1.2(4) . . . . ? C6 C7 C8 C14 0.4(4) . . . . ? C2 C1 C11 C12 2.0(3) . . . . ? C2 C1 C11 C9 -172.7(2) . . . . ? O9 C9 C11 C12 -96.0(2) . . . . ? C14 C9 C11 C12 21.7(3) . . . . ? C15 C9 C11 C12 147.5(2) . . . . ? O9 C9 C11 C1 78.5(3) . . . . ? C14 C9 C11 C1 -163.9(2) . . . . ? C15 C9 C11 C1 -38.0(3) . . . . ? C1 C11 C12 C4 -0.8(4) . . . . ? C9 C11 C12 C4 173.9(2) . . . . ? C1 C11 C12 O10 -179.6(2) . . . . ? C9 C11 C12 O10 -4.9(3) . . . . ? C3 C4 C12 C11 -0.2(4) . . . . ? C3 C4 C12 O10 178.6(2) . . . . ? C13 O10 C12 C11 -13.3(3) . . . . ? C13 O10 C12 C4 167.8(2) . . . . ? C12 O10 C13 C14 12.0(3) . . . . ? C12 O10 C13 C5 -168.6(2) . . . . ? C6 C5 C13 O10 -179.7(2) . . . . ? C6 C5 C13 C14 -0.3(4) . . . . ? C7 C8 C14 C13 -1.9(4) . . . . ? C7 C8 C14 C9 171.8(2) . . . . ? O10 C13 C14 C8 -178.8(2) . . . . ? C5 C13 C14 C8 1.9(3) . . . . ? O10 C13 C14 C9 7.4(3) . . . . ? C5 C13 C14 C9 -172.0(2) . . . . ? O9 C9 C14 C8 -78.4(3) . . . . ? C11 C9 C14 C8 163.7(2) . . . . ? C15 C9 C14 C8 38.0(3) . . . . ? O9 C9 C14 C13 95.1(2) . . . . ? C11 C9 C14 C13 -22.8(3) . . . . ? C15 C9 C14 C13 -148.6(2) . . . . ? O9 C9 C15 C16 179.9(2) . . . . ? C11 C9 C15 C16 -62.1(3) . . . . ? C14 C9 C15 C16 62.4(3) . . . . ? O9 C9 C15 C20 -1.2(3) . . . . ? C11 C9 C15 C20 116.8(2) . . . . ? C14 C9 C15 C20 -118.8(2) . . . . ? C20 C15 C16 C17 -0.8(4) . . . . ? C9 C15 C16 C17 178.0(2) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C21 O11 C18 C19 177.7(2) . . . . ? C21 O11 C18 C17 -1.1(4) . . . . ? C16 C17 C18 O11 179.2(2) . . . . ? C16 C17 C18 C19 0.4(4) . . . . ? O11 C18 C19 C20 -179.7(2) . . . . ? C17 C18 C19 C20 -0.8(4) . . . . ? C18 C19 C20 C15 0.4(4) . . . . ? C16 C15 C20 C19 0.4(3) . . . . ? C9 C15 C20 C19 -178.4(2) . . . . ? C4G C1G C3G C5G -177.1(9) . . . . ? C5G C1G C3G C2G -1.2(10) . . . 2_575 ? C4G C1G C3G C2G -178.3(7) . . . 2_575 ? C5G C1G C3G C4G 177.1(9) . . . . ? C5G C1G C3G C2G 178.1(7) . . . . ? C4G C1G C3G C2G 1.0(9) . . . . ? C5G C1G C3G C3G 170(17) . . . 2_575 ? C4G C1G C3G C3G -8(17) . . . 2_575 ? C5G C1G C3G Cl1G 166(15) . . . . ? C4G C1G C3G Cl1G -11(14) . . . . ? C4G C2G C3G C5G 153(9) . . . . ? C5G C2G C3G C5G -27(10) 2_575 . . . ? C3G C2G C3G C5G -25(9) 2_575 . . . ? C4G C2G C3G C1G -1.2(11) . . . . ? C5G C2G C3G C1G 178.8(10) 2_575 . . . ? C3G C2G C3G C1G -179.4(12) 2_575 . . . ? C4G C2G C3G C2G 178.2(6) . . . 2_575 ? C5G C2G C3G C2G -1.8(7) 2_575 . . 2_575 ? C3G C2G C3G C2G 0.0 2_575 . . 2_575 ? C5G C2G C3G C4G -180.0(6) 2_575 . . . ? C3G C2G C3G C4G -178.2(6) 2_575 . . . ? C4G C2G C3G C3G 178.2(6) . . . 2_575 ? C5G C2G C3G C3G -1.8(7) 2_575 . . 2_575 ? C4G C2G C3G Cl1G -0.3(5) . . . . ? C5G C2G C3G Cl1G 179.8(5) 2_575 . . . ? C3G C2G C3G Cl1G -178.4(8) 2_575 . . . ? C4G Cl1G C3G C5G -177.9(6) . . . . ? C5G Cl1G C3G C1G -13(14) . . . . ? C4G Cl1G C3G C1G 169(14) . . . . ? C5G Cl1G C3G C2G -0.2(5) . . . 2_575 ? C4G Cl1G C3G C2G -178.0(7) . . . 2_575 ? C5G Cl1G C3G C4G 177.9(6) . . . . ? C5G Cl1G C3G C2G 178.1(7) . . . . ? C4G Cl1G C3G C2G 0.2(4) . . . . ? C5G Cl1G C3G C3G 168(5) . . . 2_575 ? C4G Cl1G C3G C3G -10(5) . . . 2_575 ? C5G C2G C4G C3G 180(100) 2_575 . . . ? C3G C2G C4G C3G 2.1(7) 2_575 . . . ? C5G C2G C4G C1G -179(100) 2_575 . . . ? C3G C2G C4G C1G 3.0(11) 2_575 . . . ? C3G C2G C4G C1G 0.9(8) . . . . ? C5G C2G C4G Cl1G 180(100) 2_575 . . . ? C3G C2G C4G Cl1G 2.3(10) 2_575 . . . ? C3G C2G C4G Cl1G 0.3(6) . . . . ? C5G C3G C4G C2G -177.7(8) . . . . ? C1G C3G C4G C2G 178.9(10) . . . . ? C2G C3G C4G C2G -8(3) 2_575 . . . ? C3G C3G C4G C2G -1.6(5) 2_575 . . . ? Cl1G C3G C4G C2G 179.8(5) . . . . ? C5G C3G C4G C1G 3.4(11) . . . . ? C2G C3G C4G C1G 173(3) 2_575 . . . ? C2G C3G C4G C1G -178.9(10) . . . . ? C3G C3G C4G C1G 179.5(11) 2_575 . . . ? Cl1G C3G C4G C1G 0.8(10) . . . . ? C5G C3G C4G Cl1G 2.5(7) . . . . ? C1G C3G C4G Cl1G -0.8(10) . . . . ? C2G C3G C4G Cl1G 172(3) 2_575 . . . ? C2G C3G C4G Cl1G -179.8(5) . . . . ? C3G C3G C4G Cl1G 178.7(7) 2_575 . . . ? C3G C1G C4G C2G -1.1(10) . . . . ? C5G C1G C4G C2G -3.9(17) . . . . ? C5G C1G C4G C3G -2.9(9) . . . . ? C3G C1G C4G Cl1G 177(4) . . . . ? C5G C1G C4G Cl1G 174(4) . . . . ? C5G Cl1G C4G C2G -1.8(8) . . . . ? C3G Cl1G C4G C2G -0.3(6) . . . . ? C5G Cl1G C4G C3G -1.5(4) . . . . ? C5G Cl1G C4G C1G -4(3) . . . . ? C3G Cl1G C4G C1G -2(3) . . . . ? C2G C3G C5G C1G 178.8(10) 2_575 . . . ? C4G C3G C5G C1G -3.6(12) . . . . ? C2G C3G C5G C1G -155(9) . . . . ? C3G C3G C5G C1G -179.2(12) 2_575 . . . ? Cl1G C3G C5G C1G -1.0(11) . . . . ? C1G C3G C5G C2G -178.8(10) . . . 2_575 ? C4G C3G C5G C2G 177.6(8) . . . 2_575 ? C2G C3G C5G C2G 26(9) . . . 2_575 ? C3G C3G C5G C2G 2.0(7) 2_575 . . 2_575 ? Cl1G C3G C5G C2G -179.9(5) . . . 2_575 ? C1G C3G C5G Cl1G 1.0(11) . . . . ? C2G C3G C5G Cl1G 179.9(5) 2_575 . . . ? C4G C3G C5G Cl1G -2.6(8) . . . . ? C2G C3G C5G Cl1G -154(9) . . . . ? C3G C3G C5G Cl1G -178.2(8) 2_575 . . . ? C4G C1G C5G C3G 2.9(9) . . . . ? C3G C1G C5G C2G 1.3(10) . . . 2_575 ? C4G C1G C5G C2G 4.2(18) . . . 2_575 ? C3G C1G C5G Cl1G -175(5) . . . . ? C4G C1G C5G Cl1G -172(6) . . . . ? C4G Cl1G C5G C3G 1.6(5) . . . . ? C3G Cl1G C5G C1G 5(5) . . . . ? C4G Cl1G C5G C1G 6(5) . . . . ? C3G Cl1G C5G C2G 0.2(6) . . . 2_575 ? C4G Cl1G C5G C2G 1.8(9) . . . 2_575 ? 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 O9 H9 O10 0.966(2) 1.905(3) 2.871(2) 178(3) 2_566 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.219 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 934128' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 O3.C3.50 H4' _chemical_formula_sum 'C23.50 H20 O3' _chemical_formula_weight 350.40 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3923(3) _cell_length_b 9.0879(4) _cell_length_c 12.7002(7) _cell_angle_alpha 95.557(2) _cell_angle_beta 96.234(2) _cell_angle_gamma 110.261(3) _cell_volume 893.88(7) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 15266 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour colourles _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 370 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9692 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15266 _diffrn_reflns_av_R_equivalents 0.1077 _diffrn_reflns_av_sigmaI/netI 0.1547 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3119 _reflns_number_gt 1433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0382P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 3119 _refine_ls_number_parameters 258 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1452 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 O9 O 0.2815(2) 0.7873(2) 0.53174(14) 0.0300(5) Uani 1 1 d D . . H9 H 0.213(4) 0.694(3) 0.481(2) 0.126(15) Uiso 1 1 d D . . O10 O -0.0726(2) 0.4878(2) 0.61770(13) 0.0315(5) Uani 1 1 d . . . O11 O 0.6845(2) 1.3362(2) 0.90513(15) 0.0435(6) Uani 1 1 d . . . C1 C 0.3873(3) 0.6241(3) 0.7226(2) 0.0305(7) Uani 1 1 d . . . H1 H 0.4879 0.7170 0.7352 0.037 Uiso 1 1 calc R . . C2 C 0.3983(3) 0.4844(3) 0.7501(2) 0.0329(8) Uani 1 1 d . . . H2 H 0.5059 0.4813 0.7797 0.039 Uiso 1 1 calc R . . C3 C 0.2523(3) 0.3486(3) 0.7345(2) 0.0357(8) Uani 1 1 d . . . H3 H 0.2594 0.2522 0.7533 0.043 Uiso 1 1 calc R . . C4 C 0.0968(3) 0.3536(3) 0.6916(2) 0.0326(8) Uani 1 1 d . . . H4 H -0.0043 0.2613 0.6819 0.039 Uiso 1 1 calc R . . C5 C -0.2668(3) 0.6145(3) 0.5792(2) 0.0317(8) Uani 1 1 d . . . H5 H -0.3566 0.5136 0.5694 0.038 Uiso 1 1 calc R . . C6 C -0.3026(3) 0.7499(4) 0.5663(2) 0.0339(8) Uani 1 1 d . . . H6 H -0.4179 0.7422 0.5461 0.041 Uiso 1 1 calc R . . C7 C -0.1710(3) 0.8967(3) 0.5827(2) 0.0341(8) Uani 1 1 d . . . H7 H -0.1958 0.9898 0.5752 0.041 Uiso 1 1 calc R . . C8 C -0.0035(3) 0.9064(3) 0.6100(2) 0.0324(7) Uani 1 1 d . . . H8 H 0.0862 1.0075 0.6218 0.039 Uiso 1 1 calc R . . C9 C 0.2234(3) 0.7812(3) 0.6359(2) 0.0256(7) Uani 1 1 d . . . C11 C 0.2327(3) 0.6327(3) 0.6769(2) 0.0250(7) Uani 1 1 d . . . C12 C 0.0890(3) 0.4946(3) 0.6628(2) 0.0267(7) Uani 1 1 d . . . C13 C -0.0966(3) 0.6297(3) 0.6069(2) 0.0260(7) Uani 1 1 d . . . C14 C 0.0376(3) 0.7722(3) 0.62057(19) 0.0234(7) Uani 1 1 d . . . C15 C 0.3451(3) 0.9318(3) 0.7069(2) 0.0237(7) Uani 1 1 d . . . C16 C 0.3211(3) 0.9601(3) 0.8123(2) 0.0299(7) Uani 1 1 d . . . H16 H 0.2267 0.8870 0.8374 0.036 Uiso 1 1 calc R . . C17 C 0.4317(3) 1.0929(3) 0.8822(2) 0.0317(7) Uani 1 1 d . . . H17 H 0.4142 1.1096 0.9544 0.038 Uiso 1 1 calc R . . C18 C 0.5670(3) 1.1995(3) 0.8447(2) 0.0311(8) Uani 1 1 d . . . C19 C 0.5920(3) 1.1747(3) 0.7401(2) 0.0318(7) Uani 1 1 d . . . H19 H 0.6852 1.2490 0.7147 0.038 Uiso 1 1 calc R . . C20 C 0.4808(3) 1.0410(3) 0.6713(2) 0.0296(7) Uani 1 1 d . . . H20 H 0.4987 1.0249 0.5991 0.035 Uiso 1 1 calc R . . C21 C 0.6604(4) 1.3686(3) 1.0135(2) 0.0542(10) Uani 1 1 d . . . H21A H 0.5485 1.3798 1.0145 0.081 Uiso 1 1 calc R . . H21B H 0.7517 1.4672 1.0484 0.081 Uiso 1 1 calc R . . H21C H 0.6644 1.2811 1.0518 0.081 Uiso 1 1 calc R . . C1G C 0.1363(6) 1.2373(7) 0.0988(5) 0.0993(18) Uani 1 1 d . . . C2G C 0.0654(5) 0.9397(7) 0.0632(3) 0.0688(12) Uani 1 1 d . . . C3G C 0.0503(9) 1.0784(13) 0.0376(7) 0.068(2) Uani 0.50 1 d P . . C4G C 0.1518(10) 1.0934(17) 0.1252(7) 0.099(4) Uani 0.50 1 d P . . C5G C 0.0154(14) 1.2102(12) -0.0059(12) 0.109(4) Uani 0.50 1 d P . . 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 O9 0.0295(11) 0.0321(13) 0.0278(11) 0.0032(10) 0.0055(9) 0.0104(10) O10 0.0230(11) 0.0245(12) 0.0434(12) 0.0018(9) -0.0026(9) 0.0072(9) O11 0.0471(13) 0.0346(14) 0.0373(12) -0.0037(10) -0.0027(10) 0.0054(10) C1 0.0277(17) 0.0250(19) 0.0359(18) 0.0006(15) 0.0023(14) 0.0079(14) C2 0.0319(18) 0.033(2) 0.0382(18) 0.0045(15) 0.0003(14) 0.0183(16) C3 0.0386(18) 0.0245(19) 0.0446(19) 0.0068(15) -0.0009(16) 0.0137(16) C4 0.0309(17) 0.0238(19) 0.0409(19) 0.0042(15) 0.0023(15) 0.0082(14) C5 0.0261(17) 0.0287(19) 0.0377(18) 0.0031(15) 0.0015(14) 0.0079(14) C6 0.0259(17) 0.042(2) 0.0356(18) 0.0029(16) 0.0036(14) 0.0150(16) C7 0.0314(18) 0.033(2) 0.0430(19) 0.0073(15) 0.0065(15) 0.0169(16) C8 0.0273(17) 0.0297(19) 0.0375(18) 0.0020(14) 0.0037(14) 0.0080(14) C9 0.0265(16) 0.0269(18) 0.0243(16) 0.0026(14) 0.0031(13) 0.0115(14) C11 0.0251(16) 0.0213(18) 0.0277(16) 0.0009(13) 0.0015(13) 0.0087(14) C12 0.0227(16) 0.0278(19) 0.0311(17) 0.0034(14) 0.0017(14) 0.0119(15) C13 0.0280(17) 0.0228(19) 0.0313(17) 0.0036(14) 0.0058(14) 0.0140(15) C14 0.0217(15) 0.0200(17) 0.0275(16) 0.0038(13) 0.0011(13) 0.0071(14) C15 0.0213(16) 0.0218(17) 0.0290(17) 0.0041(13) 0.0006(13) 0.0099(13) C16 0.0311(17) 0.0230(18) 0.0340(18) 0.0089(14) 0.0073(14) 0.0058(14) C17 0.0412(18) 0.0290(19) 0.0269(17) 0.0061(15) 0.0068(15) 0.0139(15) C18 0.0301(18) 0.0274(19) 0.0314(19) -0.0021(15) -0.0042(15) 0.0090(15) C19 0.0245(16) 0.0289(19) 0.0405(19) 0.0072(15) 0.0046(14) 0.0073(14) C20 0.0250(16) 0.0307(19) 0.0315(17) 0.0018(15) 0.0040(14) 0.0090(15) C21 0.070(2) 0.044(2) 0.0367(19) -0.0052(17) -0.0045(18) 0.0120(18) C1G 0.074(4) 0.090(4) 0.111(4) -0.005(4) 0.038(3) 0.000(3) C2G 0.045(3) 0.102(4) 0.075(4) 0.048(3) 0.027(3) 0.030(3) C3G 0.030(6) 0.102(10) 0.061(8) 0.011(6) 0.034(6) 0.004(5) C4G 0.030(5) 0.168(13) 0.039(6) -0.019(6) 0.012(4) -0.030(6) C5G 0.093(8) 0.050(7) 0.220(13) 0.052(8) 0.123(9) 0.031(6) _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 O9 C9 1.458(3) . ? O9 H9 0.966(2) . ? O10 C13 1.390(3) . ? O10 C12 1.391(3) . ? O11 C18 1.381(3) . ? O11 C21 1.430(3) . ? C1 C2 1.379(3) . ? C1 C11 1.394(3) . ? C1 H1 0.9500 . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.375(3) . ? C3 H3 0.9500 . ? C4 C12 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(3) . ? C5 C13 1.389(3) . ? C5 H5 0.9500 . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.381(3) . ? C7 H7 0.9500 . ? C8 C14 1.392(3) . ? C8 H8 0.9500 . ? C9 C11 1.516(3) . ? C9 C14 1.523(3) . ? C9 C15 1.524(3) . ? C11 C12 1.387(3) . ? C13 C14 1.371(3) . ? C15 C20 1.380(3) . ? C15 C16 1.387(3) . ? C16 C17 1.395(3) . ? C16 H16 0.9500 . ? C17 C18 1.378(4) . ? C17 H17 0.9500 . ? C18 C19 1.377(3) . ? C19 C20 1.394(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C1G C4G 1.426(13) . ? C1G C3G 1.467(10) . ? C1G C5G 1.527(14) . ? C2G C3G 1.376(11) . ? C2G C5G 1.381(10) 2_575 ? C2G C4G 1.434(11) . ? C2G C3G 1.479(10) 2_575 ? C3G C4G 1.291(12) . ? C3G C5G 1.470(15) . ? C3G C2G 1.479(10) 2_575 ? C3G C3G 1.543(18) 2_575 ? C5G C2G 1.381(10) 2_575 ? 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 C9 O9 H9 111(2) . . ? C13 O10 C12 118.1(2) . . ? C18 O11 C21 116.8(2) . . ? C2 C1 C11 121.8(2) . . ? C2 C1 H1 119.1 . . ? C11 C1 H1 119.1 . . ? C1 C2 C3 119.8(3) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C12 119.4(3) . . ? C3 C4 H4 120.3 . . ? C12 C4 H4 120.3 . . ? C6 C5 C13 118.4(3) . . ? C6 C5 H5 120.8 . . ? C13 C5 H5 120.8 . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 119.4(3) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C14 121.8(3) . . ? C7 C8 H8 119.1 . . ? C14 C8 H8 119.1 . . ? O9 C9 C11 108.2(2) . . ? O9 C9 C14 107.99(19) . . ? C11 C9 C14 109.5(2) . . ? O9 C9 C15 105.7(2) . . ? C11 C9 C15 112.3(2) . . ? C14 C9 C15 112.9(2) . . ? C12 C11 C1 116.7(2) . . ? C12 C11 C9 121.1(2) . . ? C1 C11 C9 122.0(2) . . ? C11 C12 C4 122.3(2) . . ? C11 C12 O10 122.2(2) . . ? C4 C12 O10 115.5(2) . . ? C14 C13 C5 123.1(3) . . ? C14 C13 O10 122.4(2) . . ? C5 C13 O10 114.5(2) . . ? C13 C14 C8 117.0(2) . . ? C13 C14 C9 121.4(2) . . ? C8 C14 C9 121.4(2) . . ? C20 C15 C16 118.2(2) . . ? C20 C15 C9 122.6(2) . . ? C16 C15 C9 119.1(2) . . ? C15 C16 C17 121.8(3) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 118.8(3) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C19 C18 C17 120.4(2) . . ? C19 C18 O11 115.0(3) . . ? C17 C18 O11 124.6(2) . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 120.6(2) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? O11 C21 H21A 109.5 . . ? O11 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O11 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C4G C1G C3G 53.0(6) . . ? C4G C1G C5G 111.8(6) . . ? C3G C1G C5G 58.8(5) . . ? C3G C2G C5G 127.1(8) . 2_575 ? C3G C2G C4G 54.7(6) . . ? C5G C2G C4G 178.2(8) 2_575 . ? C3G C2G C3G 65.3(7) . 2_575 ? C5G C2G C3G 61.8(7) 2_575 2_575 ? C4G C2G C3G 120.0(9) . 2_575 ? C4G C3G C2G 65.0(9) . . ? C4G C3G C1G 61.9(7) . . ? C2G C3G C1G 126.9(8) . . ? C4G C3G C5G 124.5(11) . . ? C2G C3G C5G 170.5(10) . . ? C1G C3G C5G 62.6(7) . . ? C4G C3G C2G 179.5(12) . 2_575 ? C2G C3G C2G 114.7(7) . 2_575 ? C1G C3G C2G 118.5(10) . 2_575 ? C5G C3G C2G 55.8(7) . 2_575 ? C4G C3G C3G 125.6(16) . 2_575 ? C2G C3G C3G 60.6(8) . 2_575 ? C1G C3G C3G 172.5(14) . 2_575 ? C5G C3G C3G 109.9(12) . 2_575 ? C2G C3G C3G 54.1(6) 2_575 2_575 ? C3G C4G C1G 65.1(9) . . ? C3G C4G C2G 60.4(6) . . ? C1G C4G C2G 125.5(8) . . ? C2G C5G C3G 62.4(6) 2_575 . ? C2G C5G C1G 121.0(8) 2_575 . ? C3G C5G C1G 58.6(6) . . ? 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 C11 C1 C2 C3 -1.4(4) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C12 1.1(4) . . . . ? C13 C5 C6 C7 -1.1(4) . . . . ? C5 C6 C7 C8 1.3(4) . . . . ? C6 C7 C8 C14 0.6(4) . . . . ? C2 C1 C11 C12 1.6(4) . . . . ? C2 C1 C11 C9 -173.5(2) . . . . ? O9 C9 C11 C12 -96.4(3) . . . . ? C14 C9 C11 C12 21.1(3) . . . . ? C15 C9 C11 C12 147.4(2) . . . . ? O9 C9 C11 C1 78.5(3) . . . . ? C14 C9 C11 C1 -164.0(2) . . . . ? C15 C9 C11 C1 -37.8(3) . . . . ? C1 C11 C12 C4 -0.5(4) . . . . ? C9 C11 C12 C4 174.6(2) . . . . ? C1 C11 C12 O10 -179.8(2) . . . . ? C9 C11 C12 O10 -4.6(4) . . . . ? C3 C4 C12 C11 -0.9(4) . . . . ? C3 C4 C12 O10 178.5(2) . . . . ? C13 O10 C12 C11 -13.3(3) . . . . ? C13 O10 C12 C4 167.4(2) . . . . ? C6 C5 C13 C14 -1.0(4) . . . . ? C6 C5 C13 O10 -179.7(2) . . . . ? C12 O10 C13 C14 12.1(3) . . . . ? C12 O10 C13 C5 -169.2(2) . . . . ? C5 C13 C14 C8 2.8(4) . . . . ? O10 C13 C14 C8 -178.6(2) . . . . ? C5 C13 C14 C9 -171.5(2) . . . . ? O10 C13 C14 C9 7.1(4) . . . . ? C7 C8 C14 C13 -2.6(4) . . . . ? C7 C8 C14 C9 171.7(2) . . . . ? O9 C9 C14 C13 95.3(3) . . . . ? C11 C9 C14 C13 -22.4(3) . . . . ? C15 C9 C14 C13 -148.3(2) . . . . ? O9 C9 C14 C8 -78.8(3) . . . . ? C11 C9 C14 C8 163.6(2) . . . . ? C15 C9 C14 C8 37.7(3) . . . . ? O9 C9 C15 C20 -1.5(3) . . . . ? C11 C9 C15 C20 116.3(3) . . . . ? C14 C9 C15 C20 -119.3(3) . . . . ? O9 C9 C15 C16 179.6(2) . . . . ? C11 C9 C15 C16 -62.6(3) . . . . ? C14 C9 C15 C16 61.8(3) . . . . ? C20 C15 C16 C17 -1.3(4) . . . . ? C9 C15 C16 C17 177.7(2) . . . . ? C15 C16 C17 C18 0.9(4) . . . . ? C16 C17 C18 C19 0.0(4) . . . . ? C16 C17 C18 O11 179.3(2) . . . . ? C21 O11 C18 C19 178.3(2) . . . . ? C21 O11 C18 C17 -1.0(4) . . . . ? C17 C18 C19 C20 -0.3(4) . . . . ? O11 C18 C19 C20 -179.7(2) . . . . ? C16 C15 C20 C19 0.9(4) . . . . ? C9 C15 C20 C19 -178.0(2) . . . . ? C18 C19 C20 C15 -0.2(4) . . . . ? C5G C2G C3G C4G 179.9(6) 2_575 . . . ? C3G C2G C3G C4G -179.7(7) 2_575 . . . ? C5G C2G C3G C1G 179.9(5) 2_575 . . . ? C4G C2G C3G C1G 0.0(6) . . . . ? C3G C2G C3G C1G -179.7(9) 2_575 . . . ? C5G C2G C3G C5G -2(4) 2_575 . . . ? C4G C2G C3G C5G 178(4) . . . . ? C3G C2G C3G C5G -2(3) 2_575 . . . ? C5G C2G C3G C2G -0.4(7) 2_575 . . 2_575 ? C4G C2G C3G C2G 179.7(7) . . . 2_575 ? C3G C2G C3G C2G 0.0 2_575 . . 2_575 ? C5G C2G C3G C3G -0.4(7) 2_575 . . 2_575 ? C4G C2G C3G C3G 179.7(7) . . . 2_575 ? C5G C1G C3G C4G 179.6(7) . . . . ? C4G C1G C3G C2G 0.0(6) . . . . ? C5G C1G C3G C2G 179.6(8) . . . . ? C4G C1G C3G C5G -179.6(7) . . . . ? C4G C1G C3G C2G -179.7(7) . . . 2_575 ? C5G C1G C3G C2G -0.1(5) . . . 2_575 ? C4G C1G C3G C3G -178(6) . . . 2_575 ? C5G C1G C3G C3G 1(5) . . . 2_575 ? C2G C3G C4G C1G -180.0(5) . . . . ? C5G C3G C4G C1G 0.5(7) . . . . ? C2G C3G C4G C1G 140(100) 2_575 . . . ? C3G C3G C4G C1G 179.7(9) 2_575 . . . ? C1G C3G C4G C2G 180.0(5) . . . . ? C5G C3G C4G C2G -179.6(8) . . . . ? C2G C3G C4G C2G -40(100) 2_575 . . . ? C3G C3G C4G C2G -0.3(7) 2_575 . . . ? C5G C1G C4G C3G -0.4(6) . . . . ? C3G C1G C4G C2G 0.0(6) . . . . ? C5G C1G C4G C2G -0.4(9) . . . . ? C5G C2G C4G C3G -178(100) 2_575 . . . ? C3G C2G C4G C3G 0.3(7) 2_575 . . . ? C3G C2G C4G C1G 0.0(6) . . . . ? C5G C2G C4G C1G -178(100) 2_575 . . . ? C3G C2G C4G C1G 0.4(9) 2_575 . . . ? C4G C3G C5G C2G 179.6(7) . . . 2_575 ? C2G C3G C5G C2G 2(4) . . . 2_575 ? C1G C3G C5G C2G -179.9(5) . . . 2_575 ? C3G C3G C5G C2G 0.3(6) 2_575 . . 2_575 ? C4G C3G C5G C1G -0.5(7) . . . . ? C2G C3G C5G C1G -178(4) . . . . ? C2G C3G C5G C1G 179.9(5) 2_575 . . . ? C3G C3G C5G C1G -179.8(7) 2_575 . . . ? C4G C1G C5G C2G 0.5(9) . . . 2_575 ? C3G C1G C5G C2G 0.1(5) . . . 2_575 ? C4G C1G C5G C3G 0.4(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 O9 H9 O10 0.966(2) 1.906(3) 2.872(2) 179(3) 2_566 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.210 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 934129'