# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Anthony Coleman' _publ_contact_author_address ; IBCP CNRS 7 passage du Vercors Lyon 69367 FRANCE ; _publ_contact_author_email AW.COLEMAN@IBCP.FR _publ_section_title ; Amphiphilic Behavior of an Apparently Non-polar Calix-arene ; loop_ _publ_author_name 'Anthony Coleman' 'Srinivasan S. Kuduva' 'Patrick Shahgaldian' 'Michael J. Zaworotko' data_france2 _database_code_depnum_ccdc_archive 'CCDC 249102' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C76 H120 O4' _chemical_formula_weight 1097.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.760(3) _cell_length_b 19.969(3) _cell_length_c 36.601(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 13711(4) _cell_formula_units_Z 8 _cell_measurement_temperature 175(2) _cell_measurement_reflns_used 6367 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 23.84 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.064 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4864 _exptl_absorpt_coefficient_mu 0.063 _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 175(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 118361 _diffrn_reflns_av_R_equivalents 0.2481 _diffrn_reflns_av_sigmaI/netI 0.1585 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 28.36 _reflns_number_total 16731 _reflns_number_gt 6593 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0676P)^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 SHELXL _refine_ls_extinction_coef 0.00087(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 16731 _refine_ls_number_parameters 722 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2120 _refine_ls_R_factor_gt 0.0985 _refine_ls_wR_factor_ref 0.1870 _refine_ls_wR_factor_gt 0.1460 _refine_ls_goodness_of_fit_ref 0.875 _refine_ls_restrained_S_all 0.875 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.76152(9) 0.47318(9) 0.17778(5) 0.0403(5) Uani 1 1 d . . . O2 O 0.69245(9) 0.63359(9) 0.15367(5) 0.0404(5) Uani 1 1 d . . . O3 O 0.93525(9) 0.45444(9) 0.17466(5) 0.0425(5) Uani 1 1 d . . . O4 O 0.86746(9) 0.61064(9) 0.16645(5) 0.0397(5) Uani 1 1 d . . . C5 C 0.75627(15) 0.24386(14) 0.01427(7) 0.0473(7) Uani 1 1 d . . . H5A H 0.8078 0.2450 0.0124 0.057 Uiso 1 1 calc R . . H5B H 0.7437 0.2072 0.0304 0.057 Uiso 1 1 calc R . . C6 C 0.70551(13) 0.63765(13) 0.19113(7) 0.0349(6) Uani 1 1 d . . . C7 C 0.72447(14) 0.44378(13) 0.20639(7) 0.0363(6) Uani 1 1 d . . . C8 C 0.75918(15) 0.32093(14) 0.06972(7) 0.0476(8) Uani 1 1 d . . . H8A H 0.7430 0.2848 0.0854 0.057 Uiso 1 1 calc R . . H8B H 0.8108 0.3194 0.0691 0.057 Uiso 1 1 calc R . . C9 C 0.72559(16) 0.22979(15) -0.02332(8) 0.0506(8) Uani 1 1 d . . . H9A H 0.6742 0.2262 -0.0213 0.061 Uiso 1 1 calc R . . H9B H 0.7359 0.2676 -0.0391 0.061 Uiso 1 1 calc R . . C10 C 0.76537(15) 0.39913(14) 0.12448(7) 0.0443(7) Uani 1 1 d . . . H10A H 0.7556 0.3603 0.1396 0.053 Uiso 1 1 calc R . . H10B H 0.8167 0.4047 0.1232 0.053 Uiso 1 1 calc R . . C11 C 0.72066(15) 0.15005(16) -0.07756(8) 0.0524(8) Uani 1 1 d . . . H11A H 0.6699 0.1435 -0.0741 0.063 Uiso 1 1 calc R . . H11B H 0.7268 0.1880 -0.0938 0.063 Uiso 1 1 calc R . . C12 C 0.61288(16) 0.52076(15) 0.02950(7) 0.0536(8) Uani 1 1 d . . . H12A H 0.5754 0.4944 0.0408 0.064 Uiso 1 1 calc R . . H12B H 0.6581 0.5004 0.0360 0.064 Uiso 1 1 calc R . . C13 C 0.62958(14) 0.53284(13) 0.20024(7) 0.0412(7) Uani 1 1 d . . . H13A H 0.5801 0.5390 0.2072 0.049 Uiso 1 1 calc R . . H13B H 0.6320 0.5310 0.1738 0.049 Uiso 1 1 calc R . . C14 C 0.75969(15) 0.39616(13) 0.22715(7) 0.0390(7) Uani 1 1 d . . . C15 C 0.87378(16) 0.46090(16) -0.04258(8) 0.0539(8) Uani 1 1 d . . . H15A H 0.8717 0.4980 -0.0597 0.065 Uiso 1 1 calc R . . H15B H 0.9236 0.4502 -0.0386 0.065 Uiso 1 1 calc R . . C16 C 0.84127(16) 0.48273(16) -0.00676(8) 0.0521(8) Uani 1 1 d . . . H16A H 0.7914 0.4934 -0.0107 0.062 Uiso 1 1 calc R . . H16B H 0.8434 0.4456 0.0103 0.062 Uiso 1 1 calc R . . C17 C 0.73328(15) 0.45982(14) 0.14187(7) 0.0456(7) Uani 1 1 d . . . H17A H 0.7420 0.4983 0.1263 0.055 Uiso 1 1 calc R . . H17B H 0.6821 0.4537 0.1437 0.055 Uiso 1 1 calc R . . C18 C 0.60827(17) 0.44741(16) -0.02699(8) 0.0573(9) Uani 1 1 d . . . H18A H 0.5719 0.4203 -0.0154 0.069 Uiso 1 1 calc R . . H18B H 0.6542 0.4284 -0.0206 0.069 Uiso 1 1 calc R . . C19 C 1.00005(15) 0.33442(15) 0.05207(7) 0.0499(8) Uani 1 1 d . . . H19A H 0.9916 0.2989 0.0696 0.060 Uiso 1 1 calc R . . H19B H 1.0512 0.3406 0.0501 0.060 Uiso 1 1 calc R . . C20 C 0.62942(16) 0.66784(15) 0.14266(8) 0.0516(8) Uani 1 1 d . . . H20A H 0.6317 0.7143 0.1503 0.062 Uiso 1 1 calc R . . H20B H 0.5881 0.6474 0.1540 0.062 Uiso 1 1 calc R . . C21 C 0.73647(15) 0.38672(14) 0.08644(7) 0.0470(8) Uani 1 1 d . . . H21A H 0.6848 0.3880 0.0874 0.056 Uiso 1 1 calc R . . H21B H 0.7520 0.4228 0.0706 0.056 Uiso 1 1 calc R . . C22 C 0.60293(18) 0.37251(16) -0.08283(8) 0.0600(9) Uani 1 1 d . . . H22A H 0.5666 0.3457 -0.0710 0.072 Uiso 1 1 calc R . . H22B H 0.6488 0.3537 -0.0762 0.072 Uiso 1 1 calc R . . C23 C 0.61965(16) 0.59354(15) 0.08652(7) 0.0513(8) Uani 1 1 d . . . H23A H 0.5802 0.5702 0.0979 0.062 Uiso 1 1 calc R . . H23B H 0.6631 0.5701 0.0931 0.062 Uiso 1 1 calc R . . C24 C 0.87749(16) 0.54253(15) 0.01013(7) 0.0517(8) Uani 1 1 d . . . H24A H 0.8721 0.5805 -0.0062 0.062 Uiso 1 1 calc R . . H24B H 0.9280 0.5331 0.0123 0.062 Uiso 1 1 calc R . . C25 C 0.90641(14) 0.66232(14) 0.18153(7) 0.0385(7) Uani 1 1 d . . . C26 C 0.71708(17) 0.07104(17) -0.13196(8) 0.0610(9) Uani 1 1 d . . . H26A H 0.6666 0.0633 -0.1281 0.073 Uiso 1 1 calc R . . H26B H 0.7218 0.1089 -0.1484 0.073 Uiso 1 1 calc R . . C27 C 0.59373(17) 0.36575(15) -0.12366(8) 0.0536(8) Uani 1 1 d . . . H27A H 0.5483 0.3853 -0.1304 0.064 Uiso 1 1 calc R . . H27B H 0.6307 0.3916 -0.1356 0.064 Uiso 1 1 calc R . . C28 C 0.95960(13) 0.53508(14) 0.22173(7) 0.0390(7) Uani 1 1 d . . . C29 C 0.59892(17) 0.44228(16) -0.06773(8) 0.0559(9) Uani 1 1 d . . . H29A H 0.5530 0.4613 -0.0742 0.067 Uiso 1 1 calc R . . H29B H 0.6353 0.4693 -0.0794 0.067 Uiso 1 1 calc R . . C30 C 0.73112(16) 0.30893(15) 0.03143(7) 0.0498(8) Uani 1 1 d . . . H30A H 0.7458 0.3459 0.0160 0.060 Uiso 1 1 calc R . . H30B H 0.6794 0.3088 0.0322 0.060 Uiso 1 1 calc R . . C31 C 0.65760(14) 0.46855(13) 0.21621(7) 0.0373(6) Uani 1 1 d . . . C32 C 0.60432(17) 0.51681(16) -0.01144(7) 0.0553(9) Uani 1 1 d . . . H32A H 0.5586 0.5362 -0.0180 0.066 Uiso 1 1 calc R . . H32B H 0.6411 0.5439 -0.0227 0.066 Uiso 1 1 calc R . . C33 C 0.75280(14) 0.68592(13) 0.20370(7) 0.0348(6) Uani 1 1 d . . . C34 C 0.67407(13) 0.59110(13) 0.21428(7) 0.0359(6) Uani 1 1 d . . . C35 C 0.84909(16) 0.56176(15) 0.04744(7) 0.0502(8) Uani 1 1 d . . . H35A H 0.7983 0.5702 0.0455 0.060 Uiso 1 1 calc R . . H35B H 0.8557 0.5244 0.0640 0.060 Uiso 1 1 calc R . . C36 C 0.68892(15) 0.59605(14) 0.25129(7) 0.0419(7) Uani 1 1 d . . . H36A H 0.6681 0.5658 0.2674 0.050 Uiso 1 1 calc R . . C37 C 0.83723(16) 0.40100(16) -0.05939(8) 0.0560(8) Uani 1 1 d . . . H37A H 0.8388 0.3642 -0.0421 0.067 Uiso 1 1 calc R . . H37B H 0.7875 0.4120 -0.0635 0.067 Uiso 1 1 calc R . . C38 C 0.75102(15) 0.08872(15) -0.09584(7) 0.0491(8) Uani 1 1 d . . . H38A H 0.7458 0.0509 -0.0794 0.059 Uiso 1 1 calc R . . H38B H 0.8016 0.0957 -0.0997 0.059 Uiso 1 1 calc R . . C39 C 0.92634(14) 0.47675(14) 0.21058(7) 0.0381(7) Uani 1 1 d . . . C40 C 0.99440(16) 0.42326(15) 0.10276(7) 0.0526(8) Uani 1 1 d . . . H40A H 1.0448 0.4333 0.1005 0.063 Uiso 1 1 calc R . . H40B H 0.9700 0.4647 0.1087 0.063 Uiso 1 1 calc R . . C41 C 0.83774(15) 0.38130(13) 0.22016(8) 0.0446(7) Uani 1 1 d . . . H41A H 0.8515 0.3407 0.2329 0.054 Uiso 1 1 calc R . . H41B H 0.8456 0.3746 0.1942 0.054 Uiso 1 1 calc R . . C42 C 0.62308(17) 0.66375(15) 0.10174(8) 0.0539(8) Uani 1 1 d . . . H42A H 0.6636 0.6865 0.0909 0.065 Uiso 1 1 calc R . . H42B H 0.5805 0.6876 0.0943 0.065 Uiso 1 1 calc R . . C43 C 0.97561(17) 0.23127(16) -0.03792(8) 0.0582(9) Uani 1 1 d . . . H43A H 0.9273 0.2155 -0.0339 0.070 Uiso 1 1 calc R . . H43B H 0.9726 0.2706 -0.0534 0.070 Uiso 1 1 calc R . . C44 C 0.98080(18) 0.76496(17) 0.21355(9) 0.0597(9) Uani 1 1 d . . . H44A H 1.0069 0.8003 0.2233 0.072 Uiso 1 1 calc R . . C45 C 0.98182(17) 0.15456(17) -0.09302(8) 0.0580(9) Uani 1 1 d . . . H45A H 0.9364 0.1341 -0.0870 0.070 Uiso 1 1 calc R . . H45B H 0.9718 0.1933 -0.1082 0.070 Uiso 1 1 calc R . . C46 C 1.00565(16) 0.25254(15) -0.00166(8) 0.0505(8) Uani 1 1 d . . . H46A H 1.0014 0.2154 0.0153 0.061 Uiso 1 1 calc R . . H46B H 1.0561 0.2617 -0.0047 0.061 Uiso 1 1 calc R . . C47 C 0.86950(16) 0.37798(16) -0.09492(8) 0.0568(9) Uani 1 1 d . . . H47A H 0.9193 0.3674 -0.0909 0.068 Uiso 1 1 calc R . . H47B H 0.8674 0.4145 -0.1124 0.068 Uiso 1 1 calc R . . C48 C 0.76628(15) 0.68857(13) 0.24087(7) 0.0405(7) Uani 1 1 d . . . H48A H 0.7978 0.7204 0.2499 0.049 Uiso 1 1 calc R . . C49 C 0.88491(17) 0.62292(15) 0.06339(8) 0.0534(8) Uani 1 1 d . . . H49A H 0.8766 0.6605 0.0471 0.064 Uiso 1 1 calc R . . H49B H 0.9359 0.6150 0.0641 0.064 Uiso 1 1 calc R . . C50 C 0.61054(17) 0.59012(15) 0.04532(7) 0.0527(8) Uani 1 1 d . . . H50A H 0.5652 0.6104 0.0390 0.063 Uiso 1 1 calc R . . H50B H 0.6478 0.6167 0.0340 0.063 Uiso 1 1 calc R . . C51 C 0.62291(16) 0.43785(14) 0.24519(8) 0.0466(7) Uani 1 1 d . . . H51A H 0.5770 0.4513 0.2514 0.056 Uiso 1 1 calc R . . C52 C 1.01458(18) 0.17887(16) -0.05832(8) 0.0614(9) Uani 1 1 d . . . H52A H 1.0207 0.1407 -0.0423 0.074 Uiso 1 1 calc R . . H52B H 1.0617 0.1959 -0.0639 0.074 Uiso 1 1 calc R . . C53 C 0.5841(2) 0.28875(18) -0.17845(9) 0.0807(12) Uani 1 1 d . . . H53A H 0.5860 0.2422 -0.1850 0.121 Uiso 1 1 calc R . . H53B H 0.6203 0.3128 -0.1915 0.121 Uiso 1 1 calc R . . H53C H 0.5381 0.3066 -0.1846 0.121 Uiso 1 1 calc R . . C54 C 0.75375(15) 0.16694(14) -0.04106(7) 0.0476(7) Uani 1 1 d . . . H54A H 0.7460 0.1297 -0.0245 0.057 Uiso 1 1 calc R . . H54B H 0.8048 0.1717 -0.0443 0.057 Uiso 1 1 calc R . . C55 C 0.72311(17) 0.36808(14) 0.25667(8) 0.0464(7) Uani 1 1 d . . . H55A H 0.7452 0.3355 0.2708 0.056 Uiso 1 1 calc R . . C56 C 0.73364(15) 0.64463(14) 0.26468(8) 0.0443(7) Uani 1 1 d . . . H56A H 0.7419 0.6479 0.2897 0.053 Uiso 1 1 calc R . . C57 C 0.87336(15) 0.72381(13) 0.18591(7) 0.0392(7) Uani 1 1 d . . . C58 C 0.79466(14) 0.73111(13) 0.17812(7) 0.0405(7) Uani 1 1 d . . . H58A H 0.7849 0.7189 0.1530 0.049 Uiso 1 1 calc R . . H58B H 0.7803 0.7773 0.1816 0.049 Uiso 1 1 calc R . . C59 C 0.86008(16) 0.64244(14) 0.10179(7) 0.0488(8) Uani 1 1 d . . . H59A H 0.8775 0.6869 0.1076 0.059 Uiso 1 1 calc R . . H59B H 0.8084 0.6436 0.1024 0.059 Uiso 1 1 calc R . . C60 C 1.0228(2) 0.10634(19) -0.11518(9) 0.0789(12) Uani 1 1 d . . . H60A H 1.0361 0.0692 -0.0996 0.095 Uiso 1 1 calc R . . H60B H 1.0664 0.1280 -0.1230 0.095 Uiso 1 1 calc R . . C61 C 0.88695(16) 0.59317(14) 0.12988(7) 0.0470(7) Uani 1 1 d . . . H61A H 0.8680 0.5491 0.1243 0.056 Uiso 1 1 calc R . . H61B H 0.9385 0.5907 0.1283 0.056 Uiso 1 1 calc R . . C62 C 0.97122(16) 0.31273(16) 0.01517(8) 0.0550(8) Uani 1 1 d . . . H62A H 0.9207 0.3037 0.0178 0.066 Uiso 1 1 calc R . . H62B H 0.9761 0.3500 -0.0017 0.066 Uiso 1 1 calc R . . C63 C 0.98424(16) 0.37484(15) 0.13377(7) 0.0520(8) Uani 1 1 d . . . H63A H 0.9374 0.3546 0.1317 0.062 Uiso 1 1 calc R . . H63B H 1.0193 0.3394 0.1316 0.062 Uiso 1 1 calc R . . C64 C 0.88232(14) 0.43950(13) 0.23362(7) 0.0366(6) Uani 1 1 d . . . C65 C 0.87518(15) 0.46232(14) 0.26924(7) 0.0449(7) Uani 1 1 d . . . H65A H 0.8472 0.4381 0.2855 0.054 Uiso 1 1 calc R . . C66 C 0.90794(15) 0.51911(15) 0.28109(8) 0.0477(8) Uani 1 1 d . . . H66A H 0.9026 0.5329 0.3052 0.057 Uiso 1 1 calc R . . C67 C 0.99104(15) 0.40658(15) 0.17082(8) 0.0520(8) Uani 1 1 d . . . H67A H 0.9873 0.3727 0.1897 0.062 Uiso 1 1 calc R . . H67B H 1.0370 0.4284 0.1731 0.062 Uiso 1 1 calc R . . C68 C 0.97414(15) 0.64950(15) 0.19535(7) 0.0435(7) Uani 1 1 d . . . C69 C 0.98692(19) 0.07878(18) -0.14797(9) 0.0743(11) Uani 1 1 d . . . H69A H 1.0180 0.0474 -0.1598 0.111 Uiso 1 1 calc R . . H69B H 0.9758 0.1146 -0.1645 0.111 Uiso 1 1 calc R . . H69C H 0.9438 0.0565 -0.1408 0.111 Uiso 1 1 calc R . . C70 C 0.83270(17) 0.31703(17) -0.11135(8) 0.0612(9) Uani 1 1 d . . . H70A H 0.8360 0.2802 -0.0942 0.073 Uiso 1 1 calc R . . H70B H 0.7826 0.3272 -0.1147 0.073 Uiso 1 1 calc R . . C71 C 0.94893(14) 0.55611(15) 0.25743(7) 0.0434(7) Uani 1 1 d . . . H71A H 0.9698 0.5957 0.2654 0.052 Uiso 1 1 calc R . . C72 C 0.96726(17) 0.39807(15) 0.06620(8) 0.0536(8) Uani 1 1 d . . . H72A H 0.9162 0.3913 0.0682 0.064 Uiso 1 1 calc R . . H72B H 0.9750 0.4329 0.0482 0.064 Uiso 1 1 calc R . . C73 C 0.65547(17) 0.38787(15) 0.26494(8) 0.0515(8) Uani 1 1 d . . . H73A H 0.6312 0.3674 0.2841 0.062 Uiso 1 1 calc R . . C74 C 0.7489(2) 0.01002(17) -0.15002(8) 0.0738(11) Uani 1 1 d . . . H74A H 0.7258 0.0025 -0.1731 0.111 Uiso 1 1 calc R . . H74B H 0.7421 -0.0283 -0.1346 0.111 Uiso 1 1 calc R . . H74C H 0.7989 0.0170 -0.1539 0.111 Uiso 1 1 calc R . . C75 C 1.01084(16) 0.70205(17) 0.21146(8) 0.0550(8) Uani 1 1 d . . . H75A H 1.0562 0.6948 0.2209 0.066 Uiso 1 1 calc R . . C76 C 0.5964(2) 0.29615(17) -0.13788(9) 0.0756(11) Uani 1 1 d . . . H76A H 0.5608 0.2698 -0.1251 0.091 Uiso 1 1 calc R . . H76B H 0.6427 0.2773 -0.1320 0.091 Uiso 1 1 calc R . . C77 C 0.86306(17) 0.29515(17) -0.14700(8) 0.0620(9) Uani 1 1 d . . . H77A H 0.9134 0.2856 -0.1437 0.074 Uiso 1 1 calc R . . H77B H 0.8591 0.3317 -0.1643 0.074 Uiso 1 1 calc R . . C78 C 1.00282(14) 0.57865(15) 0.19611(8) 0.0467(8) Uani 1 1 d . . . H78A H 1.0522 0.5793 0.2040 0.056 Uiso 1 1 calc R . . H78B H 1.0013 0.5599 0.1717 0.056 Uiso 1 1 calc R . . C79 C 0.82723(18) 0.23383(17) -0.16305(9) 0.0685(10) Uani 1 1 d . . . H79A H 0.8493 0.2227 -0.1859 0.103 Uiso 1 1 calc R . . H79B H 0.7776 0.2430 -0.1670 0.103 Uiso 1 1 calc R . . H79C H 0.8321 0.1969 -0.1464 0.103 Uiso 1 1 calc R . . C80 C 0.91224(17) 0.77586(15) 0.20125(8) 0.0514(8) Uani 1 1 d . . . H80A H 0.8920 0.8182 0.2032 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0356(10) 0.0507(12) 0.0347(11) -0.0006(9) 0.0041(9) 0.0001(9) O2 0.0393(11) 0.0493(12) 0.0326(11) -0.0010(9) -0.0017(8) 0.0079(9) O3 0.0426(11) 0.0556(13) 0.0295(10) -0.0077(9) -0.0017(9) 0.0186(10) O4 0.0409(11) 0.0400(11) 0.0382(11) -0.0046(9) 0.0016(9) 0.0002(9) C5 0.0468(17) 0.0513(19) 0.0437(18) -0.0044(15) 0.0024(14) -0.0024(15) C6 0.0341(15) 0.0378(16) 0.0329(16) -0.0043(13) 0.0026(12) 0.0147(13) C7 0.0404(15) 0.0318(15) 0.0367(16) -0.0092(13) 0.0055(13) -0.0042(13) C8 0.0500(19) 0.0513(19) 0.0414(18) -0.0043(15) 0.0050(14) 0.0047(15) C9 0.0491(18) 0.059(2) 0.0439(18) -0.0058(16) 0.0020(14) 0.0038(16) C10 0.0503(18) 0.0437(17) 0.0390(17) 0.0032(14) 0.0025(14) 0.0061(15) C11 0.0423(17) 0.069(2) 0.0461(19) -0.0068(17) 0.0003(14) -0.0025(16) C12 0.056(2) 0.063(2) 0.0424(19) 0.0042(16) -0.0102(15) -0.0075(17) C13 0.0338(15) 0.0441(17) 0.0457(17) -0.0068(14) 0.0063(13) 0.0022(13) C14 0.0499(17) 0.0314(15) 0.0357(16) -0.0081(13) 0.0001(14) 0.0007(13) C15 0.0491(18) 0.067(2) 0.0452(19) -0.0007(16) -0.0014(15) 0.0002(17) C16 0.0494(19) 0.065(2) 0.0417(19) 0.0012(16) -0.0007(15) -0.0007(16) C17 0.0483(17) 0.0560(19) 0.0325(16) -0.0004(14) 0.0014(13) 0.0082(15) C18 0.059(2) 0.070(2) 0.0428(19) 0.0046(17) -0.0041(16) -0.0076(18) C19 0.0473(18) 0.062(2) 0.0399(18) -0.0019(16) 0.0015(14) 0.0027(15) C20 0.0513(19) 0.054(2) 0.049(2) 0.0006(15) -0.0110(15) 0.0122(16) C21 0.0488(18) 0.054(2) 0.0381(17) 0.0017(14) 0.0026(14) 0.0048(15) C22 0.066(2) 0.067(2) 0.047(2) 0.0060(17) -0.0042(17) -0.0095(18) C23 0.0496(18) 0.062(2) 0.0421(18) 0.0071(16) -0.0093(14) -0.0035(16) C24 0.0497(18) 0.064(2) 0.0412(18) 0.0035(16) 0.0028(15) 0.0016(17) C25 0.0406(16) 0.0411(17) 0.0338(16) 0.0016(13) 0.0043(13) -0.0070(14) C26 0.056(2) 0.078(2) 0.049(2) -0.0144(18) 0.0007(16) -0.0056(18) C27 0.058(2) 0.056(2) 0.048(2) 0.0035(16) 0.0023(15) -0.0081(16) C28 0.0282(14) 0.0458(17) 0.0429(18) 0.0000(14) -0.0059(12) 0.0072(13) C29 0.061(2) 0.064(2) 0.0433(19) 0.0021(17) -0.0031(15) -0.0078(17) C30 0.0484(18) 0.059(2) 0.0415(18) -0.0034(16) 0.0036(14) 0.0020(16) C31 0.0423(16) 0.0342(15) 0.0355(16) -0.0099(13) 0.0039(13) -0.0041(13) C32 0.056(2) 0.071(2) 0.0391(19) 0.0040(16) -0.0062(15) -0.0084(17) C33 0.0370(15) 0.0293(14) 0.0381(16) -0.0013(12) 0.0040(13) 0.0065(12) C34 0.0314(14) 0.0364(16) 0.0398(17) -0.0054(13) 0.0046(12) 0.0084(12) C35 0.0488(18) 0.059(2) 0.0422(18) 0.0004(16) 0.0030(14) -0.0021(16) C36 0.0488(17) 0.0391(17) 0.0379(17) -0.0001(14) 0.0151(14) 0.0018(14) C37 0.053(2) 0.069(2) 0.046(2) -0.0026(17) -0.0008(15) -0.0029(17) C38 0.0453(17) 0.057(2) 0.0445(18) -0.0048(15) 0.0070(15) -0.0071(15) C39 0.0338(15) 0.0509(19) 0.0296(16) -0.0027(14) -0.0052(12) 0.0177(14) C40 0.057(2) 0.059(2) 0.0417(19) -0.0097(16) 0.0094(15) 0.0051(16) C41 0.0550(19) 0.0415(17) 0.0375(17) -0.0018(14) -0.0038(14) 0.0109(14) C42 0.060(2) 0.055(2) 0.0470(19) 0.0078(16) -0.0141(16) 0.0036(16) C43 0.056(2) 0.071(2) 0.048(2) -0.0150(18) -0.0045(16) -0.0006(18) C44 0.059(2) 0.062(2) 0.059(2) -0.0135(18) 0.0069(17) -0.0181(19) C45 0.060(2) 0.068(2) 0.045(2) -0.0109(17) -0.0041(16) 0.0017(18) C46 0.0573(19) 0.055(2) 0.0390(17) 0.0004(15) -0.0006(15) -0.0013(16) C47 0.0485(19) 0.070(2) 0.052(2) -0.0050(17) -0.0047(16) 0.0004(17) C48 0.0465(17) 0.0343(16) 0.0407(17) -0.0088(13) -0.0002(14) 0.0005(14) C49 0.059(2) 0.059(2) 0.0415(19) 0.0014(16) 0.0027(15) -0.0024(17) C50 0.0569(19) 0.062(2) 0.0396(18) 0.0036(16) -0.0115(15) -0.0038(17) C51 0.0461(17) 0.0437(17) 0.0501(19) -0.0101(15) 0.0143(15) -0.0066(15) C52 0.073(2) 0.062(2) 0.050(2) -0.0067(17) -0.0133(17) 0.0073(19) C53 0.110(3) 0.070(3) 0.062(3) -0.009(2) 0.015(2) -0.006(2) C54 0.0433(17) 0.0520(19) 0.0475(18) -0.0039(15) 0.0037(15) -0.0055(15) C55 0.067(2) 0.0341(16) 0.0377(18) -0.0008(13) -0.0014(15) -0.0047(15) C56 0.0580(19) 0.0418(17) 0.0332(17) -0.0049(14) 0.0050(14) 0.0010(15) C57 0.0439(16) 0.0360(17) 0.0377(17) 0.0028(13) 0.0078(13) -0.0031(14) C58 0.0497(17) 0.0294(15) 0.0425(17) 0.0001(13) 0.0033(14) 0.0058(13) C59 0.0551(19) 0.0457(18) 0.0456(19) 0.0018(15) 0.0043(15) 0.0013(15) C60 0.085(3) 0.085(3) 0.066(3) -0.026(2) -0.021(2) 0.023(2) C61 0.0484(18) 0.0509(19) 0.0417(18) -0.0088(15) -0.0022(14) 0.0039(15) C62 0.0508(19) 0.072(2) 0.0423(19) -0.0091(17) -0.0016(15) -0.0021(17) C63 0.059(2) 0.057(2) 0.0400(18) -0.0076(15) 0.0000(15) 0.0259(17) C64 0.0379(15) 0.0394(16) 0.0325(16) -0.0034(13) -0.0043(13) 0.0119(13) C65 0.0533(18) 0.0489(18) 0.0326(17) -0.0020(14) 0.0020(14) 0.0064(15) C66 0.0520(18) 0.062(2) 0.0287(16) -0.0085(15) -0.0046(14) 0.0087(16) C67 0.0525(19) 0.060(2) 0.0432(19) -0.0054(16) -0.0029(15) 0.0248(16) C68 0.0410(16) 0.0508(19) 0.0386(17) -0.0026(15) 0.0063(13) -0.0043(15) C69 0.084(3) 0.083(3) 0.055(2) -0.021(2) -0.004(2) 0.001(2) C70 0.060(2) 0.077(2) 0.047(2) -0.0059(18) 0.0016(16) -0.0012(19) C71 0.0418(16) 0.0502(19) 0.0380(18) -0.0080(15) -0.0093(14) 0.0066(14) C72 0.057(2) 0.061(2) 0.0421(19) -0.0023(16) 0.0028(15) 0.0077(17) C73 0.065(2) 0.0435(19) 0.046(2) -0.0044(15) 0.0174(16) -0.0108(16) C74 0.090(3) 0.080(3) 0.052(2) -0.0122(19) 0.014(2) -0.016(2) C75 0.0408(18) 0.067(2) 0.057(2) -0.0086(18) 0.0063(15) -0.0083(17) C76 0.109(3) 0.058(2) 0.060(2) 0.0021(19) 0.006(2) -0.004(2) C77 0.060(2) 0.077(2) 0.048(2) -0.0076(18) 0.0018(17) -0.0037(19) C78 0.0334(15) 0.063(2) 0.0433(18) -0.0034(15) -0.0015(13) 0.0030(14) C79 0.081(3) 0.070(2) 0.055(2) -0.0067(19) 0.0028(19) -0.007(2) C80 0.061(2) 0.0449(19) 0.048(2) -0.0004(15) 0.0126(16) -0.0043(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.387(3) . ? O1 C17 1.442(3) . ? O2 C6 1.395(3) . ? O2 C20 1.424(3) . ? O3 C39 1.398(3) . ? O3 C67 1.424(3) . ? O4 C25 1.380(3) . ? O4 C61 1.431(3) . ? C5 C9 1.518(4) . ? C5 C30 1.518(4) . ? C6 C33 1.389(4) . ? C6 C34 1.389(4) . ? C7 C14 1.385(4) . ? C7 C31 1.396(3) . ? C8 C21 1.511(4) . ? C8 C30 1.516(4) . ? C9 C54 1.508(4) . ? C10 C17 1.495(4) . ? C10 C21 1.514(4) . ? C11 C38 1.507(4) . ? C11 C54 1.511(4) . ? C12 C50 1.502(4) . ? C12 C32 1.509(4) . ? C13 C31 1.505(4) . ? C13 C34 1.521(4) . ? C14 C55 1.397(4) . ? C14 C41 1.516(4) . ? C15 C37 1.510(4) . ? C15 C16 1.510(4) . ? C16 C24 1.507(4) . ? C18 C32 1.500(4) . ? C18 C29 1.505(4) . ? C19 C72 1.504(4) . ? C19 C62 1.518(4) . ? C20 C42 1.505(4) . ? C22 C29 1.501(4) . ? C22 C27 1.510(4) . ? C23 C42 1.510(4) . ? C23 C50 1.519(3) . ? C24 C35 1.515(4) . ? C25 C57 1.385(4) . ? C25 C68 1.391(4) . ? C26 C74 1.509(4) . ? C26 C38 1.509(4) . ? C27 C76 1.485(4) . ? C28 C39 1.383(4) . ? C28 C71 1.387(4) . ? C28 C78 1.514(4) . ? C31 C51 1.387(4) . ? C33 C48 1.385(3) . ? C33 C58 1.519(3) . ? C34 C36 1.386(4) . ? C35 C49 1.511(4) . ? C36 C56 1.373(4) . ? C37 C47 1.507(4) . ? C39 C64 1.395(4) . ? C40 C63 1.503(4) . ? C40 C72 1.518(4) . ? C41 C64 1.514(4) . ? C43 C52 1.479(4) . ? C43 C46 1.503(4) . ? C44 C75 1.379(4) . ? C44 C80 1.380(4) . ? C45 C60 1.475(4) . ? C45 C52 1.492(4) . ? C46 C62 1.497(4) . ? C47 C70 1.523(4) . ? C48 C56 1.380(4) . ? C49 C59 1.531(4) . ? C51 C73 1.375(4) . ? C53 C76 1.510(4) . ? C55 C73 1.363(4) . ? C57 C80 1.388(4) . ? C57 C58 1.511(4) . ? C59 C61 1.510(4) . ? C60 C69 1.482(4) . ? C63 C67 1.502(4) . ? C64 C65 1.388(3) . ? C65 C66 1.361(4) . ? C66 C71 1.374(4) . ? C68 C75 1.387(4) . ? C68 C78 1.514(4) . ? C70 C77 1.489(4) . ? C77 C79 1.515(4) . ? 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 C7 O1 C17 115.2(2) . . ? C6 O2 C20 113.32(19) . . ? C39 O3 C67 113.24(19) . . ? C25 O4 C61 114.9(2) . . ? C9 C5 C30 114.6(2) . . ? C33 C6 C34 122.3(2) . . ? C33 C6 O2 118.6(2) . . ? C34 C6 O2 119.1(2) . . ? C14 C7 O1 117.7(2) . . ? C14 C7 C31 122.1(3) . . ? O1 C7 C31 119.7(2) . . ? C21 C8 C30 114.5(2) . . ? C54 C9 C5 114.3(2) . . ? C17 C10 C21 112.3(2) . . ? C38 C11 C54 114.7(3) . . ? C50 C12 C32 115.3(3) . . ? C31 C13 C34 109.2(2) . . ? C7 C14 C55 117.7(3) . . ? C7 C14 C41 120.2(2) . . ? C55 C14 C41 121.8(3) . . ? C37 C15 C16 113.5(3) . . ? C24 C16 C15 113.8(3) . . ? O1 C17 C10 112.9(2) . . ? C32 C18 C29 115.7(3) . . ? C72 C19 C62 113.7(3) . . ? O2 C20 C42 108.7(2) . . ? C8 C21 C10 114.4(2) . . ? C29 C22 C27 116.2(3) . . ? C42 C23 C50 114.4(3) . . ? C16 C24 C35 114.3(3) . . ? O4 C25 C57 118.2(2) . . ? O4 C25 C68 119.4(3) . . ? C57 C25 C68 122.0(3) . . ? C74 C26 C38 114.0(3) . . ? C76 C27 C22 115.2(3) . . ? C39 C28 C71 117.9(3) . . ? C39 C28 C78 122.9(3) . . ? C71 C28 C78 119.1(3) . . ? C22 C29 C18 115.0(3) . . ? C8 C30 C5 114.2(2) . . ? C51 C31 C7 117.5(3) . . ? C51 C31 C13 120.7(2) . . ? C7 C31 C13 121.1(2) . . ? C18 C32 C12 114.8(3) . . ? C48 C33 C6 117.9(2) . . ? C48 C33 C58 119.2(2) . . ? C6 C33 C58 122.6(2) . . ? C36 C34 C6 117.6(3) . . ? C36 C34 C13 119.7(2) . . ? C6 C34 C13 122.6(2) . . ? C49 C35 C24 113.4(2) . . ? C56 C36 C34 121.5(3) . . ? C47 C37 C15 114.3(3) . . ? C11 C38 C26 114.8(3) . . ? C28 C39 C64 122.5(2) . . ? C28 C39 O3 119.5(3) . . ? C64 C39 O3 118.0(2) . . ? C63 C40 C72 114.2(3) . . ? C64 C41 C14 109.2(2) . . ? C20 C42 C23 114.9(3) . . ? C52 C43 C46 117.4(3) . . ? C75 C44 C80 120.4(3) . . ? C60 C45 C52 117.8(3) . . ? C62 C46 C43 115.4(3) . . ? C37 C47 C70 113.7(3) . . ? C56 C48 C33 121.0(3) . . ? C35 C49 C59 115.2(2) . . ? C12 C50 C23 114.9(3) . . ? C73 C51 C31 120.9(3) . . ? C43 C52 C45 117.2(3) . . ? C9 C54 C11 115.0(3) . . ? C73 C55 C14 120.8(3) . . ? C36 C56 C48 119.7(3) . . ? C25 C57 C80 118.4(3) . . ? C25 C57 C58 120.1(2) . . ? C80 C57 C58 121.2(3) . . ? C57 C58 C33 109.4(2) . . ? C61 C59 C49 111.0(2) . . ? C45 C60 C69 116.8(3) . . ? O4 C61 C59 113.1(2) . . ? C46 C62 C19 116.2(3) . . ? C67 C63 C40 113.5(3) . . ? C65 C64 C39 116.7(3) . . ? C65 C64 C41 120.3(3) . . ? C39 C64 C41 122.7(2) . . ? C66 C65 C64 122.0(3) . . ? C65 C66 C71 120.0(3) . . ? O3 C67 C63 108.1(2) . . ? C75 C68 C25 118.0(3) . . ? C75 C68 C78 121.5(3) . . ? C25 C68 C78 120.2(3) . . ? C77 C70 C47 114.0(3) . . ? C66 C71 C28 120.8(3) . . ? C19 C72 C40 116.5(3) . . ? C55 C73 C51 120.5(3) . . ? C44 C75 C68 120.7(3) . . ? C27 C76 C53 115.5(3) . . ? C70 C77 C79 114.0(3) . . ? C68 C78 C28 111.0(2) . . ? C44 C80 C57 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.402 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.092