# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name A.W.Coleman 'Oksana Danylyuk' 'Adina Lazar' 'Florent Perret' 'Kinga Suwinska' _publ_contact_author_name 'Dr A W Coleman' _publ_contact_author_address ; CNRS Institute de Biologie et Chimie des Proteines (IBCP) 7, Passage du Vercors Lyon Cedex 7 69367 FRANCE ; _publ_contact_author_email AW.COLEMAN@IBCP.FR _publ_section_title ; Assembly of a Novel Supramolecular Synthon of Calix[4]arene Presenting Four Carboxylic Acids ; data_kaliks5 _database_code_depnum_ccdc_archive 'CCDC 289490' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H48 O12' _chemical_formula_weight 768.82 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 Tetragonal _symmetry_space_group_name_H-M P41212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, -z+3/4' '-x+1/2, y+1/2, -z+1/4' '-y, -x, -z+1/2' 'y, x, -z' 'y+1/2, -x+1/2, z+3/4' '-y+1/2, x+1/2, z+1/4' _cell_length_a 18.7120(4) _cell_length_b 18.7120(4) _cell_length_c 22.7400(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7962.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3264 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method ; 183 frames via \f rotation and 39 frames via \w rotation (rotation angle 1\% and 2*700 s per frame) ; _diffrn_detector_area_resol_mean ; 1242 (horizontal) x 1152 (vertical) pixels, CCD pixel size is 22.5 x 22.5 \mm which gives at the input a pixel of 110 x 110 \mm (with 2 x 2 binning) ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38721 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 20.81 _reflns_number_total 4157 _reflns_number_gt 3324 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0683P)^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 and difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(15) _refine_ls_number_reflns 4157 _refine_ls_number_parameters 510 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 O3A O 0.47147(17) 0.10154(18) 0.04464(11) 0.0437(8) Uani 1 1 d . . . H3AO H 0.5108 0.0825 0.0472 0.066 Uiso 1 1 calc R . . O3D O 0.39575(18) -0.00515(18) -0.54424(12) 0.0471(9) Uani 1 1 d . . . H3D H 0.4264 -0.0363 -0.5469 0.071 Uiso 1 1 calc R . . O2D O 0.40841(18) -0.02551(16) -0.44759(13) 0.0453(9) Uani 1 1 d . . . O1B O 0.12456(15) 0.12325(15) -0.24587(12) 0.0395(8) Uani 1 1 d . . . O1C O 0.25371(15) 0.30479(15) -0.24112(12) 0.0388(8) Uani 1 1 d . . . O1D O 0.33366(15) 0.13783(16) -0.33024(12) 0.0385(8) Uani 1 1 d . . . O1A O 0.30840(16) 0.09880(15) -0.16748(11) 0.0341(8) Uani 1 1 d . . . O3C O 0.40336(19) 0.32519(19) -0.06419(13) 0.0521(9) Uani 1 1 d . . . H3CO H 0.4053 0.3280 -0.0282 0.078 Uiso 1 1 calc R . . O2A O 0.49079(17) 0.08874(17) -0.05232(13) 0.0453(9) Uani 1 1 d . . . O3B O 0.0389(2) 0.0960(2) -0.43736(14) 0.0642(11) Uani 1 1 d . . . O2B O 0.1249(2) 0.0159(2) -0.45124(14) 0.0648(11) Uani 1 1 d . . . H2B H 0.1173 0.0257 -0.4858 0.097 Uiso 1 1 calc R . . C6C C 0.2237(3) 0.2835(2) -0.29433(19) 0.0355(12) Uani 1 1 d . . . C9A C 0.3823(2) 0.1428(3) -0.01838(18) 0.0402(12) Uani 1 1 d . . . H9A1 H 0.3837 0.1896 0.0000 0.048 Uiso 1 1 calc R . . H9A2 H 0.3467 0.1146 0.0022 0.048 Uiso 1 1 calc R . . C5C C 0.2664(3) 0.2766(2) -0.34383(19) 0.0424(13) Uani 1 1 d . . . O2C O 0.31063(18) 0.39893(18) -0.05071(13) 0.0499(9) Uani 1 1 d . . . C8B C 0.0409(3) 0.0780(3) -0.31495(19) 0.0490(14) Uani 1 1 d . . . H8B1 H 0.0282 0.1256 -0.3281 0.059 Uiso 1 1 calc R . . H8B2 H -0.0009 0.0477 -0.3195 0.059 Uiso 1 1 calc R . . C7B C 0.0609(2) 0.0809(3) -0.2515(2) 0.0481(13) Uani 1 1 d . . . H7B1 H 0.0225 0.1021 -0.2288 0.058 Uiso 1 1 calc R . . H7B2 H 0.0695 0.0330 -0.2367 0.058 Uiso 1 1 calc R . . C7C C 0.2604(3) 0.3811(3) -0.2352(2) 0.0494(14) Uani 1 1 d . . . H7C1 H 0.2167 0.4043 -0.2479 0.059 Uiso 1 1 calc R . . H7C2 H 0.2994 0.3984 -0.2594 0.059 Uiso 1 1 calc R . . C4B C 0.1390(3) 0.2587(3) -0.1319(2) 0.0527(15) Uani 1 1 d . . . H4B H 0.1344 0.3079 -0.1276 0.063 Uiso 1 1 calc R . . C2B C 0.1359(2) 0.1536(3) -0.19166(19) 0.0376(12) Uani 1 1 d . . . C11C C 0.3457(3) 0.2901(3) -0.34209(18) 0.0444(13) Uani 1 1 d . . . H11A H 0.3532 0.3404 -0.3338 0.053 Uiso 1 1 calc R . . H11B H 0.3649 0.2808 -0.3810 0.053 Uiso 1 1 calc R . . C10D C 0.3791(2) 0.0046(3) -0.4886(2) 0.0390(12) Uani 1 1 d . . . C3D C 0.4195(2) 0.1334(3) -0.2531(2) 0.0415(12) Uani 1 1 d . . . C3C C 0.1608(4) 0.2424(3) -0.3990(2) 0.0664(18) Uani 1 1 d . . . H3C H 0.1395 0.2293 -0.4343 0.080 Uiso 1 1 calc R . . C8A C 0.3587(3) 0.1517(2) -0.08203(17) 0.0396(12) Uani 1 1 d . . . H8A1 H 0.3966 0.1749 -0.1039 0.048 Uiso 1 1 calc R . . H8A2 H 0.3171 0.1826 -0.0833 0.048 Uiso 1 1 calc R . . C1C C 0.1501(3) 0.2677(3) -0.2947(2) 0.0435(13) Uani 1 1 d . . . C11D C 0.4123(3) 0.0527(3) -0.2500(2) 0.0492(13) Uani 1 1 d . . . H11C H 0.4352 0.0330 -0.2847 0.059 Uiso 1 1 calc R . . H11D H 0.4397 0.0366 -0.2163 0.059 Uiso 1 1 calc R . . C10A C 0.4538(3) 0.1079(2) -0.0109(2) 0.0365(12) Uani 1 1 d . . . C6A C 0.2912(3) 0.0415(2) -0.20283(17) 0.0331(12) Uani 1 1 d . . . C4A C 0.2068(3) -0.0460(2) -0.23435(19) 0.0415(13) Uani 1 1 d . . . H4A H 0.1629 -0.0687 -0.2306 0.050 Uiso 1 1 calc R . . C5A C 0.2241(3) 0.0097(2) -0.19661(17) 0.0364(12) Uani 1 1 d . . . C10C C 0.3485(3) 0.3643(3) -0.0839(2) 0.0420(12) Uani 1 1 d . . . C7D C 0.3614(3) 0.1180(3) -0.38611(18) 0.0441(13) Uani 1 1 d . . . H7D1 H 0.4037 0.0885 -0.3814 0.053 Uiso 1 1 calc R . . H7D2 H 0.3741 0.1601 -0.4086 0.053 Uiso 1 1 calc R . . C8D C 0.3030(3) 0.0765(3) -0.41705(18) 0.0437(13) Uani 1 1 d . . . H8D1 H 0.2593 0.1043 -0.4160 0.052 Uiso 1 1 calc R . . H8D2 H 0.2945 0.0324 -0.3957 0.052 Uiso 1 1 calc R . . C8C C 0.2747(3) 0.3980(3) -0.1714(2) 0.0504(14) Uani 1 1 d . . . H8C1 H 0.2815 0.4491 -0.1671 0.060 Uiso 1 1 calc R . . H8C2 H 0.2333 0.3845 -0.1482 0.060 Uiso 1 1 calc R . . C9C C 0.3396(3) 0.3597(3) -0.14793(18) 0.0467(13) Uani 1 1 d . . . H9C1 H 0.3366 0.3098 -0.1590 0.056 Uiso 1 1 calc R . . H9C2 H 0.3818 0.3796 -0.1666 0.056 Uiso 1 1 calc R . . C1B C 0.1574(3) 0.1121(3) -0.14344(18) 0.0394(13) Uani 1 1 d . . . C2D C 0.3819(2) 0.1740(3) -0.29374(18) 0.0355(12) Uani 1 1 d . . . C9D C 0.3204(3) 0.0586(3) -0.48059(18) 0.0457(13) Uani 1 1 d . . . H9D1 H 0.2775 0.0405 -0.4994 0.055 Uiso 1 1 calc R . . H9D2 H 0.3339 0.1022 -0.5007 0.055 Uiso 1 1 calc R . . C6B C 0.1666(3) 0.1462(3) -0.0899(2) 0.0515(14) Uani 1 1 d . . . H6B H 0.1800 0.1196 -0.0571 0.062 Uiso 1 1 calc R . . C1A C 0.3393(3) 0.0200(3) -0.24556(19) 0.0400(12) Uani 1 1 d . . . C4C C 0.2333(3) 0.2557(3) -0.3960(2) 0.0514(15) Uani 1 1 d . . . H4C H 0.2608 0.2505 -0.4297 0.062 Uiso 1 1 calc R . . C7A C 0.3403(3) 0.0810(2) -0.11180(18) 0.0414(13) Uani 1 1 d . . . H7A1 H 0.3831 0.0527 -0.1176 0.050 Uiso 1 1 calc R . . H7A2 H 0.3071 0.0539 -0.0879 0.050 Uiso 1 1 calc R . . C3A C 0.2539(3) -0.0683(3) -0.27742(19) 0.0477(14) Uani 1 1 d . . . H3A H 0.2415 -0.1054 -0.3027 0.057 Uiso 1 1 calc R . . C1D C 0.3883(2) 0.2471(3) -0.29813(17) 0.0356(12) Uani 1 1 d . . . C9B C 0.1008(3) 0.0493(3) -0.35370(18) 0.0492(14) Uani 1 1 d . . . H9B1 H 0.1446 0.0749 -0.3449 0.059 Uiso 1 1 calc R . . H9B2 H 0.1086 -0.0008 -0.3446 0.059 Uiso 1 1 calc R . . C11A C 0.1723(3) 0.0328(3) -0.14861(18) 0.0429(13) Uani 1 1 d . . . H11E H 0.1272 0.0085 -0.1552 0.051 Uiso 1 1 calc R . . H11F H 0.1909 0.0163 -0.1112 0.051 Uiso 1 1 calc R . . C11B C 0.1057(3) 0.2723(3) -0.2392(2) 0.0558(14) Uani 1 1 d . . . H11G H 0.1049 0.3220 -0.2269 0.067 Uiso 1 1 calc R . . H11H H 0.0571 0.2593 -0.2493 0.067 Uiso 1 1 calc R . . C5D C 0.4741(3) 0.2423(3) -0.2189(2) 0.0487(14) Uani 1 1 d . . . H5D H 0.5057 0.2656 -0.1939 0.058 Uiso 1 1 calc R . . C2C C 0.1201(3) 0.2492(3) -0.3478(3) 0.0646(17) Uani 1 1 d . . . H2C H 0.0711 0.2409 -0.3496 0.077 Uiso 1 1 calc R . . C3B C 0.1279(3) 0.2279(3) -0.1871(2) 0.0448(13) Uani 1 1 d . . . C10B C 0.0846(3) 0.0567(3) -0.4172(2) 0.0492(14) Uani 1 1 d . . . C6D C 0.4354(3) 0.2807(3) -0.25999(19) 0.0458(13) Uani 1 1 d . . . H6D H 0.4412 0.3300 -0.2621 0.055 Uiso 1 1 calc R . . C4D C 0.4655(3) 0.1693(3) -0.21500(19) 0.0495(14) Uani 1 1 d . . . H4D H 0.4906 0.1438 -0.1867 0.059 Uiso 1 1 calc R . . C2A C 0.3195(3) -0.0352(3) -0.28260(18) 0.0480(14) Uani 1 1 d . . . H2A H 0.3510 -0.0502 -0.3116 0.058 Uiso 1 1 calc R . . C5B C 0.1563(3) 0.2183(3) -0.0844(2) 0.0579(16) Uani 1 1 d . . . H5B H 0.1611 0.2399 -0.0478 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3A 0.048(2) 0.044(2) 0.0388(18) -0.0001(15) -0.0029(16) 0.0003(19) O3D 0.044(2) 0.054(3) 0.0437(18) 0.0039(16) -0.0020(16) -0.0060(18) O2D 0.049(2) 0.038(2) 0.0487(18) 0.0064(17) -0.0027(17) 0.0021(18) O1B 0.028(2) 0.038(2) 0.0521(18) 0.0059(16) 0.0039(15) -0.0032(15) O1C 0.038(2) 0.023(2) 0.0554(19) 0.0062(15) 0.0031(16) 0.0019(15) O1D 0.030(2) 0.041(2) 0.0442(18) 0.0003(15) 0.0059(15) -0.0043(17) O1A 0.042(2) 0.0229(18) 0.0376(16) 0.0003(15) 0.0006(14) 0.0044(16) O3C 0.051(2) 0.053(2) 0.0519(18) -0.0123(17) 0.0040(18) 0.004(2) O2A 0.043(2) 0.048(2) 0.0450(18) -0.0066(16) 0.0043(17) -0.0043(18) O3B 0.058(3) 0.070(3) 0.064(2) -0.0004(19) -0.0029(19) 0.032(2) O2B 0.068(3) 0.074(3) 0.0532(19) -0.006(2) -0.006(2) 0.027(2) C6C 0.037(3) 0.025(3) 0.044(3) 0.009(2) -0.010(3) -0.001(2) C9A 0.041(3) 0.036(3) 0.044(3) -0.003(2) -0.001(2) -0.005(3) C5C 0.052(4) 0.030(3) 0.045(3) 0.013(2) -0.003(3) -0.004(3) O2C 0.046(2) 0.048(2) 0.0562(19) -0.0047(18) 0.0122(18) 0.003(2) C8B 0.039(3) 0.049(4) 0.059(3) 0.010(3) 0.002(3) -0.005(3) C7B 0.033(3) 0.048(3) 0.064(3) 0.009(3) 0.013(3) 0.000(3) C7C 0.051(4) 0.031(4) 0.066(3) 0.001(3) 0.000(3) 0.003(3) C4B 0.044(4) 0.035(3) 0.079(4) -0.010(3) 0.030(3) 0.001(3) C2B 0.026(3) 0.035(3) 0.052(3) -0.002(3) 0.010(2) -0.006(2) C11C 0.044(4) 0.037(3) 0.052(3) -0.003(2) 0.014(3) -0.007(3) C10D 0.031(3) 0.039(3) 0.048(3) 0.006(3) -0.003(3) -0.015(3) C3D 0.028(3) 0.048(4) 0.049(3) -0.006(3) 0.004(3) 0.007(3) C3C 0.081(5) 0.048(4) 0.070(4) 0.024(3) -0.040(4) -0.017(4) C8A 0.040(3) 0.034(3) 0.045(3) -0.003(2) 0.001(2) -0.002(3) C1C 0.038(4) 0.030(3) 0.062(3) 0.018(2) -0.009(3) 0.003(3) C11D 0.045(4) 0.052(4) 0.050(3) -0.001(3) 0.005(3) 0.020(3) C10A 0.040(3) 0.029(3) 0.041(3) -0.002(2) -0.001(3) -0.013(2) C6A 0.041(3) 0.024(3) 0.035(2) -0.001(2) -0.009(2) 0.009(3) C4A 0.047(3) 0.025(3) 0.053(3) 0.001(2) -0.015(3) 0.000(2) C5A 0.046(3) 0.030(3) 0.033(2) 0.002(2) -0.007(2) 0.004(3) C10C 0.033(3) 0.030(3) 0.063(4) 0.004(3) -0.003(3) -0.005(3) C7D 0.034(3) 0.050(3) 0.048(3) -0.002(2) 0.002(2) -0.003(3) C8D 0.032(3) 0.048(3) 0.051(3) 0.000(2) -0.001(2) 0.000(3) C8C 0.051(4) 0.038(3) 0.062(3) -0.007(3) 0.001(3) -0.006(3) C9C 0.041(3) 0.044(3) 0.055(3) 0.000(2) 0.005(2) 0.005(3) C1B 0.038(3) 0.034(3) 0.047(3) 0.000(3) 0.010(2) -0.008(3) C2D 0.025(3) 0.047(4) 0.035(2) -0.003(2) 0.005(2) 0.000(3) C9D 0.038(3) 0.043(3) 0.056(3) 0.006(2) -0.006(2) -0.007(3) C6B 0.053(4) 0.051(4) 0.051(3) 0.001(3) 0.013(3) -0.005(3) C1A 0.044(4) 0.032(3) 0.043(3) 0.003(3) 0.000(3) 0.012(3) C4C 0.075(5) 0.035(3) 0.044(3) 0.009(2) -0.008(3) -0.009(3) C7A 0.044(3) 0.032(3) 0.049(3) 0.002(2) -0.003(2) 0.007(2) C3A 0.072(5) 0.028(3) 0.043(3) -0.005(2) -0.021(3) 0.013(3) C1D 0.028(3) 0.039(4) 0.039(2) 0.003(2) 0.005(2) -0.006(2) C9B 0.047(4) 0.050(4) 0.050(3) -0.001(2) -0.002(3) 0.007(3) C11A 0.044(3) 0.040(3) 0.044(3) 0.007(2) -0.004(2) -0.005(3) C11B 0.034(3) 0.028(3) 0.105(4) 0.007(3) 0.005(3) 0.003(3) C5D 0.026(3) 0.064(4) 0.056(3) -0.015(3) 0.008(3) 0.003(3) C2C 0.050(4) 0.048(4) 0.095(4) 0.033(3) -0.032(4) -0.007(3) C3B 0.027(3) 0.034(4) 0.073(4) 0.006(3) 0.014(2) 0.004(2) C10B 0.039(4) 0.043(3) 0.065(4) -0.008(3) 0.003(3) 0.011(3) C6D 0.038(3) 0.047(3) 0.053(3) -0.006(3) 0.016(3) -0.001(3) C4D 0.034(3) 0.069(4) 0.046(3) -0.007(3) 0.008(3) 0.013(3) C2A 0.067(4) 0.040(3) 0.037(3) -0.004(3) -0.006(3) 0.026(3) C5B 0.063(4) 0.052(4) 0.059(3) -0.016(3) 0.024(3) -0.007(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 O3A C10A 1.311(5) . ? O3A H3AO 0.8200 . ? O3D C10D 1.316(5) . ? O3D H3D 0.8200 . ? O2D C10D 1.219(5) . ? O1B C2B 1.374(5) . ? O1B C7B 1.436(5) . ? O1C C6C 1.392(5) . ? O1C C7C 1.440(6) . ? O1D C2D 1.401(5) . ? O1D C7D 1.422(5) . ? O1A C6A 1.378(5) . ? O1A C7A 1.439(5) . ? O3C C10C 1.338(6) . ? O3C H3CO 0.8200 . ? O2A C10A 1.222(5) . ? O3B C10B 1.217(6) . ? O2B C10B 1.324(6) . ? O2B H2B 0.8200 . ? C6C C5C 1.385(6) . ? C6C C1C 1.410(7) . ? C9A C10A 1.499(6) . ? C9A C8A 1.522(6) . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C5C C4C 1.394(6) . ? C5C C11C 1.506(7) . ? O2C C10C 1.221(5) . ? C8B C7B 1.491(6) . ? C8B C9B 1.523(6) . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C7C C8C 1.508(6) . ? C7C H7C1 0.9700 . ? C7C H7C2 0.9700 . ? C4B C5B 1.357(7) . ? C4B C3B 1.396(6) . ? C4B H4B 0.9300 . ? C2B C1B 1.402(6) . ? C2B C3B 1.403(6) . ? C11C C1D 1.511(6) . ? C11C H11A 0.9700 . ? C11C H11B 0.9700 . ? C10D C9D 1.504(6) . ? C3D C2D 1.387(6) . ? C3D C4D 1.394(7) . ? C3D C11D 1.518(6) . ? C3C C4C 1.381(8) . ? C3C C2C 1.397(8) . ? C3C H3C 0.9300 . ? C8A C7A 1.524(6) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C1C C2C 1.376(7) . ? C1C C11B 1.512(7) . ? C11D C1A 1.501(7) . ? C11D H11C 0.9700 . ? C11D H11D 0.9700 . ? C6A C1A 1.384(6) . ? C6A C5A 1.397(6) . ? C4A C3A 1.381(6) . ? C4A C5A 1.388(6) . ? C4A H4A 0.9300 . ? C5A C11A 1.522(6) . ? C10C C9C 1.468(6) . ? C7D C8D 1.513(6) . ? C7D H7D1 0.9700 . ? C7D H7D2 0.9700 . ? C8D C9D 1.519(6) . ? C8D H8D1 0.9700 . ? C8D H8D2 0.9700 . ? C8C C9C 1.506(7) . ? C8C H8C1 0.9700 . ? C8C H8C2 0.9700 . ? C9C H9C1 0.9700 . ? C9C H9C2 0.9700 . ? C1B C6B 1.386(6) . ? C1B C11A 1.515(7) . ? C2D C1D 1.376(6) . ? C9D H9D1 0.9700 . ? C9D H9D2 0.9700 . ? C6B C5B 1.370(7) . ? C6B H6B 0.9300 . ? C1A C2A 1.383(6) . ? C4C H4C 0.9300 . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C3A C2A 1.381(7) . ? C3A H3A 0.9300 . ? C1D C6D 1.388(6) . ? C9B C10B 1.482(6) . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? C11A H11E 0.9700 . ? C11A H11F 0.9700 . ? C11B C3B 1.507(6) . ? C11B H11G 0.9700 . ? C11B H11H 0.9700 . ? C5D C4D 1.377(7) . ? C5D C6D 1.384(6) . ? C5D H5D 0.9300 . ? C2C H2C 0.9300 . ? C6D H6D 0.9300 . ? C4D H4D 0.9300 . ? C2A H2A 0.9300 . ? C5B H5B 0.9300 . ? 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 C10A O3A H3AO 109.5 . . ? C10D O3D H3D 109.5 . . ? C2B O1B C7B 115.9(3) . . ? C6C O1C C7C 113.6(3) . . ? C2D O1D C7D 114.9(3) . . ? C6A O1A C7A 115.5(3) . . ? C10C O3C H3CO 109.5 . . ? C10B O2B H2B 109.5 . . ? C5C C6C O1C 120.1(4) . . ? C5C C6C C1C 122.6(4) . . ? O1C C6C C1C 117.3(4) . . ? C10A C9A C8A 114.5(4) . . ? C10A C9A H9A1 108.6 . . ? C8A C9A H9A1 108.6 . . ? C10A C9A H9A2 108.6 . . ? C8A C9A H9A2 108.6 . . ? H9A1 C9A H9A2 107.6 . . ? C6C C5C C4C 117.5(5) . . ? C6C C5C C11C 122.0(4) . . ? C4C C5C C11C 120.5(4) . . ? C7B C8B C9B 112.8(4) . . ? C7B C8B H8B1 109.0 . . ? C9B C8B H8B1 109.0 . . ? C7B C8B H8B2 109.0 . . ? C9B C8B H8B2 109.0 . . ? H8B1 C8B H8B2 107.8 . . ? O1B C7B C8B 108.4(4) . . ? O1B C7B H7B1 110.0 . . ? C8B C7B H7B1 110.0 . . ? O1B C7B H7B2 110.0 . . ? C8B C7B H7B2 110.0 . . ? H7B1 C7B H7B2 108.4 . . ? O1C C7C C8C 108.3(4) . . ? O1C C7C H7C1 110.0 . . ? C8C C7C H7C1 110.0 . . ? O1C C7C H7C2 110.0 . . ? C8C C7C H7C2 110.0 . . ? H7C1 C7C H7C2 108.4 . . ? C5B C4B C3B 121.4(5) . . ? C5B C4B H4B 119.3 . . ? C3B C4B H4B 119.3 . . ? O1B C2B C1B 121.1(4) . . ? O1B C2B C3B 117.4(4) . . ? C1B C2B C3B 121.4(4) . . ? C5C C11C C1D 116.6(4) . . ? C5C C11C H11A 108.1 . . ? C1D C11C H11A 108.1 . . ? C5C C11C H11B 108.1 . . ? C1D C11C H11B 108.1 . . ? H11A C11C H11B 107.3 . . ? O2D C10D O3D 124.4(4) . . ? O2D C10D C9D 123.1(4) . . ? O3D C10D C9D 112.4(4) . . ? C2D C3D C4D 117.6(5) . . ? C2D C3D C11D 122.1(4) . . ? C4D C3D C11D 120.3(5) . . ? C4C C3C C2C 118.5(5) . . ? C4C C3C H3C 120.7 . . ? C2C C3C H3C 120.7 . . ? C9A C8A C7A 113.1(4) . . ? C9A C8A H8A1 108.9 . . ? C7A C8A H8A1 108.9 . . ? C9A C8A H8A2 108.9 . . ? C7A C8A H8A2 108.9 . . ? H8A1 C8A H8A2 107.8 . . ? C2C C1C C6C 117.2(5) . . ? C2C C1C C11B 121.5(5) . . ? C6C C1C C11B 121.4(4) . . ? C1A C11D C3D 119.3(4) . . ? C1A C11D H11C 107.5 . . ? C3D C11D H11C 107.5 . . ? C1A C11D H11D 107.5 . . ? C3D C11D H11D 107.5 . . ? H11C C11D H11D 107.0 . . ? O2A C10A O3A 124.9(5) . . ? O2A C10A C9A 123.1(4) . . ? O3A C10A C9A 112.0(4) . . ? O1A C6A C1A 119.0(4) . . ? O1A C6A C5A 118.8(4) . . ? C1A C6A C5A 122.1(4) . . ? C3A C4A C5A 121.1(5) . . ? C3A C4A H4A 119.4 . . ? C5A C4A H4A 119.4 . . ? C4A C5A C6A 117.8(4) . . ? C4A C5A C11A 120.5(5) . . ? C6A C5A C11A 121.6(4) . . ? O2C C10C O3C 121.9(4) . . ? O2C C10C C9C 125.3(5) . . ? O3C C10C C9C 112.8(4) . . ? O1D C7D C8D 106.6(4) . . ? O1D C7D H7D1 110.4 . . ? C8D C7D H7D1 110.4 . . ? O1D C7D H7D2 110.4 . . ? C8D C7D H7D2 110.4 . . ? H7D1 C7D H7D2 108.6 . . ? C7D C8D C9D 113.6(4) . . ? C7D C8D H8D1 108.8 . . ? C9D C8D H8D1 108.8 . . ? C7D C8D H8D2 108.8 . . ? C9D C8D H8D2 108.8 . . ? H8D1 C8D H8D2 107.7 . . ? C9C C8C C7C 112.6(4) . . ? C9C C8C H8C1 109.1 . . ? C7C C8C H8C1 109.1 . . ? C9C C8C H8C2 109.1 . . ? C7C C8C H8C2 109.1 . . ? H8C1 C8C H8C2 107.8 . . ? C10C C9C C8C 114.5(4) . . ? C10C C9C H9C1 108.6 . . ? C8C C9C H9C1 108.6 . . ? C10C C9C H9C2 108.6 . . ? C8C C9C H9C2 108.6 . . ? H9C1 C9C H9C2 107.6 . . ? C6B C1B C2B 117.9(5) . . ? C6B C1B C11A 119.7(4) . . ? C2B C1B C11A 122.3(4) . . ? C1D C2D C3D 123.3(4) . . ? C1D C2D O1D 119.5(4) . . ? C3D C2D O1D 117.1(4) . . ? C10D C9D C8D 114.8(4) . . ? C10D C9D H9D1 108.6 . . ? C8D C9D H9D1 108.6 . . ? C10D C9D H9D2 108.6 . . ? C8D C9D H9D2 108.6 . . ? H9D1 C9D H9D2 107.5 . . ? C5B C6B C1B 121.0(5) . . ? C5B C6B H6B 119.5 . . ? C1B C6B H6B 119.5 . . ? C2A C1A C6A 118.1(5) . . ? C2A C1A C11D 120.5(5) . . ? C6A C1A C11D 121.4(4) . . ? C3C C4C C5C 121.9(5) . . ? C3C C4C H4C 119.0 . . ? C5C C4C H4C 119.0 . . ? O1A C7A C8A 106.5(3) . . ? O1A C7A H7A1 110.4 . . ? C8A C7A H7A1 110.4 . . ? O1A C7A H7A2 110.4 . . ? C8A C7A H7A2 110.4 . . ? H7A1 C7A H7A2 108.6 . . ? C2A C3A C4A 119.4(5) . . ? C2A C3A H3A 120.3 . . ? C4A C3A H3A 120.3 . . ? C2D C1D C6D 117.4(4) . . ? C2D C1D C11C 122.1(4) . . ? C6D C1D C11C 120.5(4) . . ? C10B C9B C8B 112.3(4) . . ? C10B C9B H9B1 109.1 . . ? C8B C9B H9B1 109.1 . . ? C10B C9B H9B2 109.1 . . ? C8B C9B H9B2 109.1 . . ? H9B1 C9B H9B2 107.9 . . ? C1B C11A C5A 116.8(4) . . ? C1B C11A H11E 108.1 . . ? C5A C11A H11E 108.1 . . ? C1B C11A H11F 108.1 . . ? C5A C11A H11F 108.1 . . ? H11E C11A H11F 107.3 . . ? C3B C11B C1C 118.3(4) . . ? C3B C11B H11G 107.7 . . ? C1C C11B H11G 107.7 . . ? C3B C11B H11H 107.7 . . ? C1C C11B H11H 107.7 . . ? H11G C11B H11H 107.1 . . ? C4D C5D C6D 119.8(5) . . ? C4D C5D H5D 120.1 . . ? C6D C5D H5D 120.1 . . ? C1C C2C C3C 122.2(5) . . ? C1C C2C H2C 118.9 . . ? C3C C2C H2C 118.9 . . ? C4B C3B C2B 117.4(5) . . ? C4B C3B C11B 121.4(5) . . ? C2B C3B C11B 121.2(4) . . ? O3B C10B O2B 121.9(4) . . ? O3B C10B C9B 124.6(5) . . ? O2B C10B C9B 113.5(5) . . ? C5D C6D C1D 121.3(5) . . ? C5D C6D H6D 119.4 . . ? C1D C6D H6D 119.4 . . ? C5D C4D C3D 120.7(5) . . ? C5D C4D H4D 119.7 . . ? C3D C4D H4D 119.7 . . ? C3A C2A C1A 121.5(5) . . ? C3A C2A H2A 119.3 . . ? C1A C2A H2A 119.3 . . ? C4B C5B C6B 120.7(5) . . ? C4B C5B H5B 119.7 . . ? C6B C5B H5B 119.7 . . ? 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 C7C O1C C6C C5C 84.1(5) . . . . ? C7C O1C C6C C1C -97.7(5) . . . . ? O1C C6C C5C C4C -179.5(4) . . . . ? C1C C6C C5C C4C 2.4(7) . . . . ? O1C C6C C5C C11C 1.3(6) . . . . ? C1C C6C C5C C11C -176.9(4) . . . . ? C2B O1B C7B C8B 156.7(4) . . . . ? C9B C8B C7B O1B 56.3(5) . . . . ? C6C O1C C7C C8C 165.4(4) . . . . ? C7B O1B C2B C1B 73.1(5) . . . . ? C7B O1B C2B C3B -109.3(4) . . . . ? C6C C5C C11C C1D 56.2(6) . . . . ? C4C C5C C11C C1D -123.1(5) . . . . ? C10A C9A C8A C7A 69.7(5) . . . . ? C5C C6C C1C C2C -4.1(7) . . . . ? O1C C6C C1C C2C 177.7(4) . . . . ? C5C C6C C1C C11B 177.0(4) . . . . ? O1C C6C C1C C11B -1.1(6) . . . . ? C2D C3D C11D C1A -52.1(6) . . . . ? C4D C3D C11D C1A 128.6(5) . . . . ? C8A C9A C10A O2A 0.9(6) . . . . ? C8A C9A C10A O3A -180.0(4) . . . . ? C7A O1A C6A C1A -95.2(4) . . . . ? C7A O1A C6A C5A 88.4(5) . . . . ? C3A C4A C5A C6A -1.3(6) . . . . ? C3A C4A C5A C11A -178.8(4) . . . . ? O1A C6A C5A C4A 177.4(3) . . . . ? C1A C6A C5A C4A 1.2(6) . . . . ? O1A C6A C5A C11A -5.1(6) . . . . ? C1A C6A C5A C11A 178.7(4) . . . . ? C2D O1D C7D C8D 177.0(4) . . . . ? O1D C7D C8D C9D 173.1(4) . . . . ? O1C C7C C8C C9C 56.2(5) . . . . ? O2C C10C C9C C8C -4.4(7) . . . . ? O3C C10C C9C C8C 175.1(4) . . . . ? C7C C8C C9C C10C -169.7(4) . . . . ? O1B C2B C1B C6B -178.9(4) . . . . ? C3B C2B C1B C6B 3.6(7) . . . . ? O1B C2B C1B C11A 2.7(7) . . . . ? C3B C2B C1B C11A -174.8(4) . . . . ? C4D C3D C2D C1D 0.4(6) . . . . ? C11D C3D C2D C1D -178.9(4) . . . . ? C4D C3D C2D O1D -177.4(4) . . . . ? C11D C3D C2D O1D 3.2(6) . . . . ? C7D O1D C2D C1D 86.8(5) . . . . ? C7D O1D C2D C3D -95.3(4) . . . . ? O2D C10D C9D C8D 3.6(6) . . . . ? O3D C10D C9D C8D -175.3(4) . . . . ? C7D C8D C9D C10D 69.2(5) . . . . ? C2B C1B C6B C5B -1.1(7) . . . . ? C11A C1B C6B C5B 177.3(5) . . . . ? O1A C6A C1A C2A -176.7(4) . . . . ? C5A C6A C1A C2A -0.4(6) . . . . ? O1A C6A C1A C11D 6.4(6) . . . . ? C5A C6A C1A C11D -177.4(4) . . . . ? C3D C11D C1A C2A 130.6(4) . . . . ? C3D C11D C1A C6A -52.5(6) . . . . ? C2C C3C C4C C5C -1.1(8) . . . . ? C6C C5C C4C C3C 0.3(7) . . . . ? C11C C5C C4C C3C 179.6(5) . . . . ? C6A O1A C7A C8A 176.7(4) . . . . ? C9A C8A C7A O1A 170.9(4) . . . . ? C5A C4A C3A C2A 0.7(6) . . . . ? C3D C2D C1D C6D 0.6(6) . . . . ? O1D C2D C1D C6D 178.4(3) . . . . ? C3D C2D C1D C11C -178.9(4) . . . . ? O1D C2D C1D C11C -1.2(6) . . . . ? C5C C11C C1D C2D 49.9(6) . . . . ? C5C C11C C1D C6D -129.7(5) . . . . ? C7B C8B C9B C10B -171.4(4) . . . . ? C6B C1B C11A C5A -126.2(5) . . . . ? C2B C1B C11A C5A 52.2(6) . . . . ? C4A C5A C11A C1B -131.7(4) . . . . ? C6A C5A C11A C1B 50.8(6) . . . . ? C2C C1C C11B C3B 123.7(5) . . . . ? C6C C1C C11B C3B -57.5(7) . . . . ? C6C C1C C2C C3C 3.3(8) . . . . ? C11B C1C C2C C3C -177.9(5) . . . . ? C4C C3C C2C C1C -0.8(8) . . . . ? C5B C4B C3B C2B -0.6(7) . . . . ? C5B C4B C3B C11B 177.5(5) . . . . ? O1B C2B C3B C4B 179.6(4) . . . . ? C1B C2B C3B C4B -2.8(7) . . . . ? O1B C2B C3B C11B 1.6(6) . . . . ? C1B C2B C3B C11B 179.2(4) . . . . ? C1C C11B C3B C4B 126.2(5) . . . . ? C1C C11B C3B C2B -55.8(7) . . . . ? C8B C9B C10B O3B 17.3(8) . . . . ? C8B C9B C10B O2B -162.7(4) . . . . ? C4D C5D C6D C1D -0.6(7) . . . . ? C2D C1D C6D C5D -0.5(6) . . . . ? C11C C1D C6D C5D 179.0(4) . . . . ? C6D C5D C4D C3D 1.6(7) . . . . ? C2D C3D C4D C5D -1.5(6) . . . . ? C11D C3D C4D C5D 177.8(4) . . . . ? C4A C3A C2A C1A 0.0(7) . . . . ? C6A C1A C2A C3A -0.2(6) . . . . ? C11D C1A C2A C3A 176.8(4) . . . . ? C3B C4B C5B C6B 3.0(8) . . . . ? C1B C6B C5B C4B -2.2(8) . . . . ? 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 O3A H3A O2D 0.82 1.85 2.666(5) 170.6 2_655 O3D H3D O2A 0.82 1.84 2.643(5) 166.9 2_654 O3C H3C O2C 0.82 1.83 2.628(4) 164.7 6 O2B H2B O3B 0.82 1.81 2.626(4) 174.3 6_554 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.375 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.037