# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Schmitzer, Andreea R. ' _publ_contact_author_email ar.schmitzer@umontreal.ca _publ_section_title ; A Molecular Chalice with Hydrophobic Walls and Hydrophilic Rim: Self-assembly and Complexation Properties ; loop_ _publ_author_name M.Vidal V.Kairouz C.DeWolf A.R.Schmitzer # Attachment '- SCHM26.cif' data_schm26 _database_code_depnum_ccdc_archive 'CCDC 831478' #TrackingRef '- SCHM26.cif' _vrf_PLAT029_schm26 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.87 RESPONSE: Due to geometrical constraints of the instrument and the use of copper radiation, we obtain consistently a data completeness lower than 100% in dependence of the crystal system and the orientation of the mounted crystal, even with appropriate data collection routines. Typical values for data completeness range from 83-92% for triclinic, 85-97% for monoclinic and 85-98% for all other crystal systems. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H38 N4 O8' _chemical_formula_sum 'C40 H38 N4 O8' _chemical_formula_weight 702.74 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4941(4) _cell_length_b 14.0115(6) _cell_length_c 14.3666(6) _cell_angle_alpha 103.151(2) _cell_angle_beta 92.589(2) _cell_angle_gamma 99.426(2) _cell_volume 1636.46(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 7744 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 67.37 _exptl_crystal_description needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.8532 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker microstar diffractometer equiped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over three different parts of the reciprocal space (99 frames total). Due to geometrical constraints of the instrument and the use of copper radiation, we obtain consistently a data completeness lower than 100% in dependence of the crystal system and the orientation of the mounted crystal, even with appropriate data collection routines. Typical values for data completeness range from 83-92% for triclinic, 85-97% for monoclinic and 85-98% for all other crystal systems. ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 26274 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 67.80 _reflns_number_total 5140 _reflns_number_gt 3876 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2.1-0 (Bruker AXS, 2006a)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006b)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'UdMX (Maris, 2004)' _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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5140 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5474(2) 0.61638(9) 0.35159(9) 0.0536(4) Uani 1 1 d . . . O2 O 0.28932(17) 0.64986(9) 0.24767(9) 0.0492(4) Uani 1 1 d . . . O3 O 0.28622(18) 0.66943(10) 0.04990(9) 0.0544(4) Uani 1 1 d . . . O4 O 0.57085(19) 0.68695(9) -0.07282(8) 0.0476(4) Uani 1 1 d . . . O5 O 0.78631(18) 0.62280(8) 0.02045(9) 0.0485(4) Uani 1 1 d . . . O6 O 0.7297(2) 0.53267(11) 0.19336(10) 0.0668(5) Uani 1 1 d . . . O7 O 0.98838(18) 0.89610(9) 0.34268(8) 0.0478(4) Uani 1 1 d . . . O8 O 0.50049(17) 1.00247(9) 0.13799(8) 0.0463(4) Uani 1 1 d . . . N1 N 0.84590(19) 1.02426(10) 0.38779(9) 0.0346(4) Uani 1 1 d . . . N2 N 0.62195(18) 1.05084(10) 0.29167(9) 0.0342(4) Uani 1 1 d . . . N3 N 0.76780(18) 1.07521(10) 0.17158(9) 0.0339(4) Uani 1 1 d . . . N4 N 0.97201(19) 1.01273(10) 0.25456(9) 0.0348(4) Uani 1 1 d . . . C1 C 0.5329(3) 0.71290(12) 0.35362(12) 0.0418(5) Uani 1 1 d . . . C2 C 0.4047(3) 0.72810(13) 0.29883(12) 0.0422(5) Uani 1 1 d . . . C3 C 0.3424(3) 0.58277(13) 0.16847(13) 0.0490(5) Uani 1 1 d . . . H39A H 0.2507 0.5298 0.1382 0.059 Uiso 1 1 calc R . . H39B H 0.4250 0.5506 0.1935 0.059 Uiso 1 1 calc R . . C4 C 0.4101(3) 0.63256(14) 0.09370(13) 0.0480(5) Uani 1 1 d . . . H38A H 0.4982 0.6882 0.1235 0.058 Uiso 1 1 calc R . . H38B H 0.4538 0.5843 0.0446 0.058 Uiso 1 1 calc R . . C5 C 0.3405(3) 0.74817(14) 0.00602(13) 0.0497(5) Uani 1 1 d . . . H40A H 0.4183 0.7995 0.0520 0.060 Uiso 1 1 calc R . . H40B H 0.2483 0.7791 -0.0082 0.060 Uiso 1 1 calc R . . C6 C 0.4186(3) 0.71618(15) -0.08570(13) 0.0518(6) Uani 1 1 d . . . H35A H 0.3451 0.6596 -0.1288 0.062 Uiso 1 1 calc R . . H35B H 0.4331 0.7719 -0.1181 0.062 Uiso 1 1 calc R . . C7 C 0.6915(2) 0.75849(13) -0.01912(11) 0.0405(5) Uani 1 1 d . . . C8 C 0.8084(2) 0.72377(12) 0.03045(12) 0.0400(5) Uani 1 1 d . . . C9 C 0.8923(3) 0.58422(14) 0.07713(13) 0.0492(5) Uani 1 1 d . . . H36A H 1.0037 0.6157 0.0719 0.059 Uiso 1 1 calc R . . H36B H 0.8825 0.5118 0.0493 0.059 Uiso 1 1 calc R . . C10 C 0.8647(3) 0.59973(15) 0.18145(14) 0.0588(6) Uani 1 1 d . . . H48A H 0.9599 0.5894 0.2177 0.071 Uiso 1 1 calc R . . H48B H 0.8483 0.6689 0.2070 0.071 Uiso 1 1 calc R . . C11 C 0.7287(3) 0.51045(15) 0.28573(14) 0.0611(6) Uani 1 1 d . . . H51A H 0.8314 0.4900 0.3004 0.073 Uiso 1 1 calc R . . H51B H 0.6418 0.4533 0.2833 0.073 Uiso 1 1 calc R . . C12 C 0.7058(3) 0.59539(15) 0.36517(15) 0.0564(6) Uani 1 1 d . . . H42A H 0.7199 0.5780 0.4277 0.068 Uiso 1 1 calc R . . H42B H 0.7866 0.6550 0.3653 0.068 Uiso 1 1 calc R . . C13 C 0.7542(2) 0.97752(12) 0.45524(11) 0.0391(5) Uani 1 1 d . . . H12A H 0.7043 1.0281 0.4977 0.047 Uiso 1 1 calc R . . H12B H 0.8284 0.9534 0.4959 0.047 Uiso 1 1 calc R . . C14 C 0.6248(2) 0.89122(12) 0.40454(11) 0.0376(5) Uani 1 1 d . . . C15 C 0.6404(3) 0.79516(13) 0.40731(11) 0.0411(5) Uani 1 1 d . . . H20 H 0.7261 0.7850 0.4466 0.049 Uiso 1 1 calc R . . C16 C 0.3866(2) 0.82437(13) 0.29800(12) 0.0416(5) Uani 1 1 d . . . H22 H 0.2970 0.8345 0.2619 0.050 Uiso 1 1 calc R . . C17 C 0.4965(2) 0.90661(12) 0.34879(11) 0.0377(5) Uani 1 1 d . . . C18 C 0.4860(2) 1.01067(12) 0.33860(12) 0.0382(5) Uani 1 1 d . . . H21A H 0.3852 1.0089 0.3004 0.046 Uiso 1 1 calc R . . H21B H 0.4841 1.0548 0.4029 0.046 Uiso 1 1 calc R . . C19 C 1.0544(2) 0.96726(13) 0.17342(11) 0.0384(5) Uani 1 1 d . . . H31A H 1.1355 0.9324 0.1960 0.046 Uiso 1 1 calc R . . H31B H 1.1105 1.0197 0.1446 0.046 Uiso 1 1 calc R . . C20 C 0.9361(2) 0.89440(12) 0.09914(11) 0.0365(5) Uani 1 1 d . . . C21 C 0.9309(2) 0.79218(12) 0.08706(12) 0.0382(5) Uani 1 1 d . . . H33 H 1.0130 0.7693 0.1184 0.046 Uiso 1 1 calc R . . C22 C 0.6999(2) 0.85956(13) -0.00970(11) 0.0403(5) Uani 1 1 d . . . H15 H 0.6231 0.8825 -0.0452 0.048 Uiso 1 1 calc R . . C23 C 0.8193(2) 0.92839(12) 0.05110(11) 0.0367(5) Uani 1 1 d . . . C24 C 0.8088(2) 1.03829(12) 0.07263(11) 0.0387(5) Uani 1 1 d . . . H19A H 0.9128 1.0770 0.0633 0.046 Uiso 1 1 calc R . . H19B H 0.7264 1.0490 0.0269 0.046 Uiso 1 1 calc R . . C25 C 0.7794(2) 1.09232(11) 0.34097(10) 0.0331(4) Uani 1 1 d . . . C26 C 0.6173(2) 1.03750(12) 0.19447(11) 0.0350(4) Uani 1 1 d . . . C27 C 0.8872(2) 1.09493(11) 0.25279(11) 0.0325(4) Uani 1 1 d . . . C28 C 0.9390(2) 0.96868(12) 0.32874(11) 0.0363(5) Uani 1 1 d . . . C29 C 0.7847(3) 1.37964(15) 0.52864(15) 0.0621(7) Uani 1 1 d . . . H50 H 0.7880 1.4440 0.5691 0.074 Uiso 1 1 calc R . . C30 C 0.8751(3) 1.31554(16) 0.55482(14) 0.0579(6) Uani 1 1 d . . . H41 H 0.9393 1.3354 0.6142 0.069 Uiso 1 1 calc R . . C31 C 0.8737(3) 1.22263(14) 0.49569(12) 0.0469(5) Uani 1 1 d . . . H45 H 0.9371 1.1791 0.5143 0.056 Uiso 1 1 calc R . . C32 C 0.7800(2) 1.19296(12) 0.40942(11) 0.0360(5) Uani 1 1 d . . . C33 C 0.6872(3) 1.25705(13) 0.38460(13) 0.0480(5) Uani 1 1 d . . . H28 H 0.6207 1.2370 0.3261 0.058 Uiso 1 1 calc R . . C34 C 0.6903(3) 1.35021(14) 0.44427(15) 0.0570(6) Uani 1 1 d . . . H43 H 0.6263 1.3938 0.4263 0.068 Uiso 1 1 calc R . . C35 C 1.2243(3) 1.36740(17) 0.28171(19) 0.0719(8) Uani 1 1 d . . . H47 H 1.2991 1.4273 0.2882 0.086 Uiso 1 1 calc R . . C36 C 1.2559(3) 1.29699(18) 0.32925(19) 0.0729(7) Uani 1 1 d . . . H52 H 1.3520 1.3091 0.3699 0.087 Uiso 1 1 calc R . . C37 C 1.1484(3) 1.20834(15) 0.31819(15) 0.0569(6) Uani 1 1 d . . . H44 H 1.1725 1.1594 0.3501 0.068 Uiso 1 1 calc R . . C38 C 1.0066(2) 1.19088(12) 0.26107(11) 0.0378(5) Uani 1 1 d . . . C39 C 0.9752(3) 1.26353(14) 0.21571(14) 0.0533(6) Uani 1 1 d . . . H46 H 0.8771 1.2534 0.1774 0.064 Uiso 1 1 calc R . . C40 C 1.0839(4) 1.35042(16) 0.22500(18) 0.0699(7) Uani 1 1 d . . . H49 H 1.0613 1.3988 0.1919 0.084 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 0.0571(13) 0.0366(7) 0.0655(8) 0.0131(6) 0.0039(7) 0.0024(7) O2 0.0440(10) 0.0452(7) 0.0494(7) 0.0023(5) 0.0076(6) -0.0063(6) O3 0.0441(10) 0.0578(8) 0.0621(8) 0.0231(7) 0.0015(7) 0.0003(7) O4 0.0462(11) 0.0464(7) 0.0419(7) -0.0007(5) 0.0002(6) 0.0015(7) O5 0.0541(10) 0.0363(7) 0.0513(7) 0.0051(5) 0.0002(7) 0.0053(6) O6 0.0754(13) 0.0598(9) 0.0580(8) 0.0105(7) 0.0122(8) -0.0056(8) O7 0.0572(11) 0.0450(7) 0.0475(7) 0.0175(6) 0.0033(6) 0.0181(7) O8 0.0397(9) 0.0586(8) 0.0366(6) 0.0087(6) -0.0043(6) 0.0031(7) N1 0.0398(11) 0.0353(7) 0.0292(6) 0.0101(5) 0.0027(6) 0.0047(7) N2 0.0315(10) 0.0399(7) 0.0298(6) 0.0088(5) 0.0032(6) 0.0014(7) N3 0.0361(10) 0.0375(7) 0.0273(6) 0.0086(5) 0.0029(6) 0.0035(6) N4 0.0374(11) 0.0358(7) 0.0323(7) 0.0091(5) 0.0051(6) 0.0074(7) C1 0.0493(15) 0.0353(9) 0.0408(9) 0.0116(7) 0.0110(9) 0.0023(8) C2 0.0417(14) 0.0403(10) 0.0396(9) 0.0067(7) 0.0085(9) -0.0040(9) C3 0.0554(16) 0.0408(10) 0.0458(10) 0.0073(8) 0.0022(9) -0.0008(9) C4 0.0468(16) 0.0511(11) 0.0460(10) 0.0114(8) 0.0042(9) 0.0084(10) C5 0.0480(15) 0.0463(10) 0.0554(11) 0.0153(9) 0.0025(10) 0.0059(9) C6 0.0532(18) 0.0520(11) 0.0445(10) 0.0094(8) -0.0076(9) -0.0010(11) C7 0.0447(14) 0.0422(10) 0.0297(8) 0.0031(7) 0.0064(8) 0.0005(9) C8 0.0455(14) 0.0368(9) 0.0356(8) 0.0049(7) 0.0095(8) 0.0050(9) C9 0.0491(16) 0.0391(10) 0.0579(11) 0.0069(8) 0.0087(10) 0.0086(9) C10 0.0674(18) 0.0482(11) 0.0575(12) 0.0122(9) 0.0051(11) 0.0014(11) C11 0.0771(19) 0.0489(11) 0.0596(12) 0.0162(9) 0.0154(12) 0.0109(11) C12 0.067(2) 0.0479(11) 0.0557(12) 0.0133(9) 0.0001(11) 0.0132(11) C13 0.0488(14) 0.0401(9) 0.0276(8) 0.0105(7) 0.0049(8) 0.0016(8) C14 0.0444(14) 0.0384(9) 0.0294(8) 0.0098(7) 0.0075(8) 0.0021(8) C15 0.0474(14) 0.0420(10) 0.0339(8) 0.0124(7) 0.0042(8) 0.0032(9) C16 0.0356(13) 0.0463(10) 0.0423(9) 0.0119(8) 0.0063(8) 0.0030(9) C17 0.0387(13) 0.0401(9) 0.0343(8) 0.0100(7) 0.0110(8) 0.0031(8) C18 0.0329(13) 0.0440(9) 0.0380(8) 0.0108(7) 0.0086(8) 0.0048(8) C19 0.0343(13) 0.0409(9) 0.0396(9) 0.0078(7) 0.0079(8) 0.0068(8) C20 0.0375(13) 0.0413(9) 0.0302(8) 0.0077(7) 0.0119(8) 0.0038(8) C21 0.0352(13) 0.0430(9) 0.0375(8) 0.0081(7) 0.0086(8) 0.0105(8) C22 0.0454(14) 0.0466(10) 0.0286(8) 0.0091(7) 0.0056(8) 0.0066(9) C23 0.0420(13) 0.0404(9) 0.0274(8) 0.0085(7) 0.0094(8) 0.0037(8) C24 0.0484(14) 0.0414(9) 0.0271(7) 0.0113(7) 0.0074(8) 0.0045(9) C25 0.0353(13) 0.0335(8) 0.0287(7) 0.0069(6) 0.0026(7) 0.0021(8) C26 0.0393(13) 0.0342(8) 0.0304(8) 0.0075(6) 0.0020(8) 0.0039(8) C27 0.0322(12) 0.0349(8) 0.0303(8) 0.0086(6) 0.0025(7) 0.0043(8) C28 0.0378(13) 0.0360(9) 0.0321(8) 0.0062(7) -0.0028(8) 0.0017(8) C29 0.0739(19) 0.0420(11) 0.0594(13) -0.0067(9) 0.0164(12) 0.0029(11) C30 0.0544(17) 0.0623(13) 0.0436(10) -0.0077(9) 0.0000(10) 0.0023(12) C31 0.0489(15) 0.0493(10) 0.0377(9) 0.0030(8) 0.0014(9) 0.0063(9) C32 0.0409(13) 0.0346(9) 0.0309(8) 0.0073(7) 0.0078(8) 0.0018(8) C33 0.0600(16) 0.0415(10) 0.0420(9) 0.0098(8) 0.0042(9) 0.0084(10) C34 0.0704(18) 0.0408(10) 0.0606(12) 0.0104(9) 0.0112(11) 0.0128(10) C35 0.065(2) 0.0462(12) 0.0940(17) 0.0081(12) 0.0261(15) -0.0131(12) C36 0.0442(17) 0.0647(15) 0.0946(17) 0.0031(13) -0.0012(13) -0.0098(12) C37 0.0481(16) 0.0498(11) 0.0674(13) 0.0115(10) -0.0023(11) -0.0012(10) C38 0.0369(14) 0.0374(9) 0.0368(8) 0.0065(7) 0.0079(8) 0.0023(8) C39 0.0578(16) 0.0458(11) 0.0574(11) 0.0203(9) 0.0063(10) 0.0009(10) C40 0.084(2) 0.0454(11) 0.0799(15) 0.0254(11) 0.0179(15) -0.0055(12) _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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . . 1.372(2) Y O1 C12 . . 1.437(3) Y O2 C2 . . 1.385(2) Y O2 C3 . . 1.442(2) Y O3 C5 . . 1.415(2) Y O3 C4 . . 1.427(3) Y O4 C7 . . 1.375(2) Y O4 C6 . . 1.436(3) Y O5 C8 . . 1.370(2) Y O5 C9 . . 1.435(3) Y O6 C10 . . 1.402(3) Y O6 C11 . . 1.430(2) Y O7 C28 . . 1.214(2) Y O8 C26 . . 1.212(2) Y N1 C28 . . 1.383(2) Y N1 C25 . . 1.454(2) Y N1 C13 . . 1.471(2) Y N2 C26 . . 1.364(2) Y N2 C25 . . 1.450(2) Y N2 C18 . . 1.461(2) Y N3 C26 . . 1.385(2) Y N3 C27 . . 1.456(2) Y N3 C24 . . 1.476(2) Y N4 C28 . . 1.366(2) Y N4 C27 . . 1.459(2) Y N4 C19 . . 1.462(2) Y C1 C2 . . 1.387(3) Y C1 C15 . . 1.395(2) Y C2 C16 . . 1.385(3) Y C3 C4 . . 1.495(2) Y C3 H39a . . 0.99 ? C3 H39b . . 0.99 ? C4 H38a . . 0.99 ? C4 H38b . . 0.99 ? C5 C6 . . 1.512(3) Y C5 H40a . . 0.99 ? C5 H40b . . 0.99 ? C6 H35a . . 0.99 ? C6 H35b . . 0.99 ? C7 C22 . . 1.381(2) Y C7 C8 . . 1.407(3) Y C8 C21 . . 1.380(3) Y C9 C10 . . 1.500(3) Y C9 H36a . . 0.99 ? C9 H36b . . 0.99 ? C10 H48a . . 0.99 ? C10 H48b . . 0.99 ? C11 C12 . . 1.495(3) Y C11 H51a . . 0.99 ? C11 H51b . . 0.99 ? C12 H42a . . 0.99 ? C12 H42b . . 0.99 ? C13 C14 . . 1.514(2) Y C13 H12a . . 0.99 ? C13 H12b . . 0.99 ? C14 C15 . . 1.383(2) Y C14 C17 . . 1.397(3) Y C15 H20 . . 0.95 ? C16 C17 . . 1.391(2) Y C16 H22 . . 0.95 ? C17 C18 . . 1.515(2) Y C18 H21a . . 0.99 ? C18 H21b . . 0.99 ? C19 C20 . . 1.504(2) Y C19 H31a . . 0.99 ? C19 H31b . . 0.99 ? C20 C23 . . 1.389(3) Y C20 C21 . . 1.396(2) Y C21 H33 . . 0.95 ? C22 C23 . . 1.392(2) Y C22 H15 . . 0.95 ? C23 C24 . . 1.518(2) Y C24 H19a . . 0.99 ? C24 H19b . . 0.99 ? C25 C32 . . 1.524(2) Y C25 C27 . . 1.600(2) Y C27 C38 . . 1.523(2) Y C29 C34 . . 1.363(3) Y C29 C30 . . 1.375(3) Y C29 H50 . . 0.95 ? C30 C31 . . 1.381(3) Y C30 H41 . . 0.95 ? C31 C32 . . 1.382(3) Y C31 H45 . . 0.95 ? C32 C33 . . 1.381(3) Y C33 C34 . . 1.385(3) Y C33 H28 . . 0.95 ? C34 H43 . . 0.95 ? C35 C40 . . 1.368(4) Y C35 C36 . . 1.374(4) Y C35 H47 . . 0.95 ? C36 C37 . . 1.389(3) Y C36 H52 . . 0.95 ? C37 C38 . . 1.381(3) Y C37 H44 . . 0.95 ? C38 C39 . . 1.381(3) Y C39 C40 . . 1.378(3) Y C39 H46 . . 0.95 ? C40 H49 . . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O1 C12 . . . 117.86(15) Y C2 O2 C3 . . . 116.09(15) Y C5 O3 C4 . . . 114.84(16) Y C7 O4 C6 . . . 116.81(15) Y C8 O5 C9 . . . 118.19(14) Y C10 O6 C11 . . . 114.57(17) Y C28 N1 C25 . . . 111.79(12) Y C28 N1 C13 . . . 118.20(14) Y C25 N1 C13 . . . 120.48(15) Y C26 N2 C25 . . . 114.05(14) Y C26 N2 C18 . . . 121.85(14) Y C25 N2 C18 . . . 123.30(13) Y C26 N3 C27 . . . 111.57(12) Y C26 N3 C24 . . . 117.28(13) Y C27 N3 C24 . . . 120.94(15) Y C28 N4 C27 . . . 113.80(14) Y C28 N4 C19 . . . 122.12(15) Y C27 N4 C19 . . . 122.66(13) Y O1 C1 C2 . . . 117.65(16) Y O1 C1 C15 . . . 123.19(19) Y C2 C1 C15 . . . 119.16(17) Y C16 C2 O2 . . . 118.43(19) Y C16 C2 C1 . . . 119.49(16) Y O2 C2 C1 . . . 122.02(17) Y O2 C3 C4 . . . 113.64(15) Y O2 C3 H39A . . . 108.8 ? C4 C3 H39A . . . 108.8 ? O2 C3 H39B . . . 108.8 ? C4 C3 H39B . . . 108.8 ? H39A C3 H39B . . . 107.7 ? O3 C4 C3 . . . 109.01(17) Y O3 C4 H38A . . . 109.9 ? C3 C4 H38A . . . 109.9 ? O3 C4 H38B . . . 109.9 ? C3 C4 H38B . . . 109.9 ? H38A C4 H38B . . . 108.3 ? O3 C5 C6 . . . 113.95(16) Y O3 C5 H40A . . . 108.8 ? C6 C5 H40A . . . 108.8 ? O3 C5 H40B . . . 108.8 ? C6 C5 H40B . . . 108.8 ? H40A C5 H40B . . . 107.7 ? O4 C6 C5 . . . 114.64(16) Y O4 C6 H35A . . . 108.6 ? C5 C6 H35A . . . 108.6 ? O4 C6 H35B . . . 108.6 ? C5 C6 H35B . . . 108.6 ? H35A C6 H35B . . . 107.6 ? O4 C7 C22 . . . 123.92(19) Y O4 C7 C8 . . . 116.16(16) Y C22 C7 C8 . . . 119.89(16) Y O5 C8 C21 . . . 125.23(18) Y O5 C8 C7 . . . 115.86(16) Y C21 C8 C7 . . . 118.86(16) Y O5 C9 C10 . . . 115.61(18) Y O5 C9 H36A . . . 108.4 ? C10 C9 H36A . . . 108.4 ? O5 C9 H36B . . . 108.4 ? C10 C9 H36B . . . 108.4 ? H36A C9 H36B . . . 107.4 ? O6 C10 C9 . . . 109.96(16) Y O6 C10 H48A . . . 109.7 ? C9 C10 H48A . . . 109.7 ? O6 C10 H48B . . . 109.7 ? C9 C10 H48B . . . 109.7 ? H48A C10 H48B . . . 108.2 ? O6 C11 C12 . . . 114.04(17) Y O6 C11 H51A . . . 108.7 ? C12 C11 H51A . . . 108.7 ? O6 C11 H51B . . . 108.7 ? C12 C11 H51B . . . 108.7 ? H51A C11 H51B . . . 107.6 ? O1 C12 C11 . . . 109.15(18) Y O1 C12 H42A . . . 109.8 ? C11 C12 H42A . . . 109.8 ? O1 C12 H42B . . . 109.8 ? C11 C12 H42B . . . 109.8 ? H42A C12 H42B . . . 108.3 ? N1 C13 C14 . . . 112.44(12) Y N1 C13 H12A . . . 109.1 ? C14 C13 H12A . . . 109.1 ? N1 C13 H12B . . . 109.1 ? C14 C13 H12B . . . 109.1 ? H12A C13 H12B . . . 107.8 ? C15 C14 C17 . . . 119.49(16) Y C15 C14 C13 . . . 119.51(18) Y C17 C14 C13 . . . 120.81(16) Y C14 C15 C1 . . . 121.38(19) Y C14 C15 H20 . . . 119.3 ? C1 C15 H20 . . . 119.3 ? C2 C16 C17 . . . 121.6(2) Y C2 C16 H22 . . . 119.2 ? C17 C16 H22 . . . 119.2 ? C16 C17 C14 . . . 118.82(17) Y C16 C17 C18 . . . 121.14(18) Y C14 C17 C18 . . . 119.88(15) Y N2 C18 C17 . . . 111.10(15) Y N2 C18 H21A . . . 109.4 ? C17 C18 H21A . . . 109.4 ? N2 C18 H21B . . . 109.4 ? C17 C18 H21B . . . 109.4 ? H21A C18 H21B . . . 108 ? N4 C19 C20 . . . 110.17(15) Y N4 C19 H31A . . . 109.6 ? C20 C19 H31A . . . 109.6 ? N4 C19 H31B . . . 109.6 ? C20 C19 H31B . . . 109.6 ? H31A C19 H31B . . . 108.1 ? C23 C20 C21 . . . 119.77(16) Y C23 C20 C19 . . . 119.72(15) Y C21 C20 C19 . . . 120.03(17) Y C8 C21 C20 . . . 121.14(19) Y C8 C21 H33 . . . 119.4 ? C20 C21 H33 . . . 119.4 ? C7 C22 C23 . . . 120.99(19) Y C7 C22 H15 . . . 119.5 ? C23 C22 H15 . . . 119.5 ? C20 C23 C22 . . . 119.23(16) Y C20 C23 C24 . . . 120.96(15) Y C22 C23 C24 . . . 119.43(18) Y N3 C24 C23 . . . 111.98(12) Y N3 C24 H19A . . . 109.2 ? C23 C24 H19A . . . 109.2 ? N3 C24 H19B . . . 109.2 ? C23 C24 H19B . . . 109.2 ? H19A C24 H19B . . . 107.9 ? N2 C25 N1 . . . 113.45(12) Y N2 C25 C32 . . . 111.13(15) Y N1 C25 C32 . . . 112.22(13) Y N2 C25 C27 . . . 101.49(12) Y N1 C25 C27 . . . 102.58(14) Y C32 C25 C27 . . . 115.34(12) Y O8 C26 N2 . . . 126.18(16) Y O8 C26 N3 . . . 125.68(14) Y N2 C26 N3 . . . 108.08(15) Y N3 C27 N4 . . . 114.04(13) Y N3 C27 C38 . . . 112.43(13) Y N4 C27 C38 . . . 110.08(15) Y N3 C27 C25 . . . 102.59(14) Y N4 C27 C25 . . . 101.40(12) Y C38 C27 C25 . . . 115.76(13) Y O7 C28 N4 . . . 126.06(17) Y O7 C28 N1 . . . 125.99(15) Y N4 C28 N1 . . . 107.88(15) Y C34 C29 C30 . . . 119.54(19) Y C34 C29 H50 . . . 120.2 ? C30 C29 H50 . . . 120.2 ? C29 C30 C31 . . . 120.7(2) Y C29 C30 H41 . . . 119.7 ? C31 C30 H41 . . . 119.7 ? C30 C31 C32 . . . 120.0(2) Y C30 C31 H45 . . . 120 ? C32 C31 H45 . . . 120 ? C33 C32 C31 . . . 118.88(16) Y C33 C32 C25 . . . 119.67(15) Y C31 C32 C25 . . . 121.45(18) Y C32 C33 C34 . . . 120.56(19) Y C32 C33 H28 . . . 119.7 ? C34 C33 H28 . . . 119.7 ? C29 C34 C33 . . . 120.3(2) Y C29 C34 H43 . . . 119.9 ? C33 C34 H43 . . . 119.9 ? C40 C35 C36 . . . 119.4(2) Y C40 C35 H47 . . . 120.3 ? C36 C35 H47 . . . 120.3 ? C35 C36 C37 . . . 120.4(2) Y C35 C36 H52 . . . 119.8 ? C37 C36 H52 . . . 119.8 ? C38 C37 C36 . . . 120.4(2) Y C38 C37 H44 . . . 119.8 ? C36 C37 H44 . . . 119.8 ? C39 C38 C37 . . . 118.34(17) Y C39 C38 C27 . . . 121.96(18) Y C37 C38 C27 . . . 119.66(16) Y C40 C39 C38 . . . 121.1(2) Y C40 C39 H46 . . . 119.4 ? C38 C39 H46 . . . 119.4 ? C35 C40 C39 . . . 120.3(2) Y C35 C40 H49 . . . 119.9 ? C39 C40 H49 . . . 119.9 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C12 O1 C1 C2 . . . . 149.98(17) Y C12 O1 C1 C15 . . . . -29.7(2) Y C3 O2 C2 C16 . . . . 115.92(19) Y C3 O2 C2 C1 . . . . -66.9(2) Y O1 C1 C2 C16 . . . . -179.27(15) Y C15 C1 C2 C16 . . . . 0.4(3) Y O1 C1 C2 O2 . . . . 3.6(2) Y C15 C1 C2 O2 . . . . -176.75(15) Y C2 O2 C3 C4 . . . . -59.4(2) Y C5 O3 C4 C3 . . . . 157.20(15) Y O2 C3 C4 O3 . . . . -64.9(2) Y C4 O3 C5 C6 . . . . 71.9(2) Y C7 O4 C6 C5 . . . . -61.9(2) Y O3 C5 C6 O4 . . . . -69.5(2) Y C6 O4 C7 C22 . . . . -26.7(2) Y C6 O4 C7 C8 . . . . 151.28(15) Y C9 O5 C8 C21 . . . . 3.9(2) Y C9 O5 C8 C7 . . . . -173.68(15) Y O4 C7 C8 O5 . . . . -1.0(2) Y C22 C7 C8 O5 . . . . 177.03(15) Y O4 C7 C8 C21 . . . . -178.77(15) Y C22 C7 C8 C21 . . . . -0.7(2) Y C8 O5 C9 C10 . . . . 74.2(2) Y C11 O6 C10 C9 . . . . 155.03(19) Y O5 C9 C10 O6 . . . . 75.9(2) Y C10 O6 C11 C12 . . . . 69.7(3) Y C1 O1 C12 C11 . . . . -128.53(16) Y O6 C11 C12 O1 . . . . 66.6(2) Y C28 N1 C13 C14 . . . . -65.5(2) Y C25 N1 C13 C14 . . . . 78.00(19) Y N1 C13 C14 C15 . . . . 110.59(18) Y N1 C13 C14 C17 . . . . -64.3(2) Y C17 C14 C15 C1 . . . . 1.7(3) Y C13 C14 C15 C1 . . . . -173.30(15) Y O1 C1 C15 C14 . . . . 177.50(16) Y C2 C1 C15 C14 . . . . -2.2(3) Y O2 C2 C16 C17 . . . . 179.09(15) Y C1 C2 C16 C17 . . . . 1.8(3) Y C2 C16 C17 C14 . . . . -2.3(3) Y C2 C16 C17 C18 . . . . 173.06(15) Y C15 C14 C17 C16 . . . . 0.5(2) Y C13 C14 C17 C16 . . . . 175.45(15) Y C15 C14 C17 C18 . . . . -174.88(15) Y C13 C14 C17 C18 . . . . 0.0(2) Y C26 N2 C18 C17 . . . . 90.0(2) Y C25 N2 C18 C17 . . . . -79.08(19) Y C16 C17 C18 N2 . . . . -112.68(18) Y C14 C17 C18 N2 . . . . 62.64(19) Y C28 N4 C19 C20 . . . . 85.2(2) Y C27 N4 C19 C20 . . . . -80.34(18) Y N4 C19 C20 C23 . . . . 64.88(19) Y N4 C19 C20 C21 . . . . -107.16(18) Y O5 C8 C21 C20 . . . . -174.54(15) Y C7 C8 C21 C20 . . . . 3.0(2) Y C23 C20 C21 C8 . . . . -2.1(2) Y C19 C20 C21 C8 . . . . 169.90(16) Y O4 C7 C22 C23 . . . . 175.50(16) Y C8 C7 C22 C23 . . . . -2.4(2) Y C21 C20 C23 C22 . . . . -1.0(2) Y C19 C20 C23 C22 . . . . -173.04(15) Y C21 C20 C23 C24 . . . . 171.87(14) Y C19 C20 C23 C24 . . . . -0.2(2) Y C7 C22 C23 C20 . . . . 3.2(2) Y C7 C22 C23 C24 . . . . -169.71(15) Y C26 N3 C24 C23 . . . . -66.1(2) Y C27 N3 C24 C23 . . . . 76.21(19) Y C20 C23 C24 N3 . . . . -64.8(2) Y C22 C23 C24 N3 . . . . 108.00(18) Y C26 N2 C25 N1 . . . . -114.47(15) Y C18 N2 C25 N1 . . . . 55.4(2) Y C26 N2 C25 C32 . . . . 117.98(15) Y C18 N2 C25 C32 . . . . -72.15(18) Y C26 N2 C25 C27 . . . . -5.17(17) Y C18 N2 C25 C27 . . . . 164.71(15) Y C28 N1 C25 N2 . . . . 92.25(17) Y C13 N1 C25 N2 . . . . -53.42(18) Y C28 N1 C25 C32 . . . . -140.76(15) Y C13 N1 C25 C32 . . . . 73.57(18) Y C28 N1 C25 C27 . . . . -16.36(17) Y C13 N1 C25 C27 . . . . -162.04(12) Y C25 N2 C26 O8 . . . . 178.60(17) Y C18 N2 C26 O8 . . . . 8.6(3) Y C25 N2 C26 N3 . . . . -4.12(19) Y C18 N2 C26 N3 . . . . -174.16(15) Y C27 N3 C26 O8 . . . . -169.78(17) Y C24 N3 C26 O8 . . . . -24.1(3) Y C27 N3 C26 N2 . . . . 12.92(19) Y C24 N3 C26 N2 . . . . 158.59(14) Y C26 N3 C27 N4 . . . . 93.37(17) Y C24 N3 C27 N4 . . . . -50.88(18) Y C26 N3 C27 C38 . . . . -140.42(15) Y C24 N3 C27 C38 . . . . 75.34(18) Y C26 N3 C27 C25 . . . . -15.39(17) Y C24 N3 C27 C25 . . . . -159.63(13) Y C28 N4 C27 N3 . . . . -112.64(15) Y C19 N4 C27 N3 . . . . 54.0(2) Y C28 N4 C27 C38 . . . . 119.92(15) Y C19 N4 C27 C38 . . . . -73.41(18) Y C28 N4 C27 C25 . . . . -3.15(17) Y C19 N4 C27 C25 . . . . 163.51(14) Y N2 C25 C27 N3 . . . . 11.78(15) Y N1 C25 C27 N3 . . . . 129.26(13) Y C32 C25 C27 N3 . . . . -108.44(16) Y N2 C25 C27 N4 . . . . -106.31(14) Y N1 C25 C27 N4 . . . . 11.16(15) Y C32 C25 C27 N4 . . . . 133.47(15) Y N2 C25 C27 C38 . . . . 134.59(15) Y N1 C25 C27 C38 . . . . -107.93(16) Y C32 C25 C27 C38 . . . . 14.4(2) Y C27 N4 C28 O7 . . . . 176.13(17) Y C19 N4 C28 O7 . . . . 9.4(3) Y C27 N4 C28 N1 . . . . -6.80(19) Y C19 N4 C28 N1 . . . . -173.55(15) Y C25 N1 C28 O7 . . . . -167.78(17) Y C13 N1 C28 O7 . . . . -21.2(3) Y C25 N1 C28 N4 . . . . 15.14(19) Y C13 N1 C28 N4 . . . . 161.68(14) Y C34 C29 C30 C31 . . . . 1.3(3) Y C29 C30 C31 C32 . . . . -0.4(3) Y C30 C31 C32 C33 . . . . -0.9(3) Y C30 C31 C32 C25 . . . . 178.06(17) Y N2 C25 C32 C33 . . . . -35.8(2) Y N1 C25 C32 C33 . . . . -164.07(16) Y C27 C25 C32 C33 . . . . 78.9(2) Y N2 C25 C32 C31 . . . . 145.19(16) Y N1 C25 C32 C31 . . . . 17.0(2) Y C27 C25 C32 C31 . . . . -100.02(19) Y C31 C32 C33 C34 . . . . 1.2(3) Y C25 C32 C33 C34 . . . . -177.76(17) Y C30 C29 C34 C33 . . . . -1.0(3) Y C32 C33 C34 C29 . . . . -0.3(3) Y C40 C35 C36 C37 . . . . 1.5(4) Y C35 C36 C37 C38 . . . . -1.5(4) Y C36 C37 C38 C39 . . . . 0.0(3) Y C36 C37 C38 C27 . . . . -177.67(19) Y N3 C27 C38 C39 . . . . 18.2(2) Y N4 C27 C38 C39 . . . . 146.57(17) Y C25 C27 C38 C39 . . . . -99.2(2) Y N3 C27 C38 C37 . . . . -164.17(17) Y N4 C27 C38 C37 . . . . -35.8(2) Y C25 C27 C38 C37 . . . . 78.4(2) Y C37 C38 C39 C40 . . . . 1.6(3) Y C27 C38 C39 C40 . . . . 179.18(19) Y C36 C35 C40 C39 . . . . 0.0(4) Y C38 C39 C40 C35 . . . . -1.6(4) Y _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 67.80 _diffrn_measured_fraction_theta_full 0.866 _refine_diff_density_max 0.294 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.038