Electronic Supplementary Material for Chemical Communications This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Juha Lintuluoto' _publ_contact_author_address ; Department of Chemistry, Graduate School of Science and Technology Kobe University Rokkodaimachi 1-1 Nada-ku Kobe 657-8501 JAPAN ; _publ_contact_author_email LINTULUO@KOBE-U.AC.JP _publ_section_title ; Direct determination of absolute configuration of carboxylic acids by cyclooctapyrrole ; loop_ _publ_author_name 'Juha Lintuluoto' 'Kana Nakayama' 'Jun-ichiro Setsune' data_o4ph _database_code_depnum_ccdc_archive 'CCDC 608298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,6,7,11,12,15,16,20,21,24,25,29,30,33,34-hexadecaethyl-9,18,27, 36-tetraphenyl[32]octaphyrin-(1.0.1.0.1.0.1.0) ; _chemical_name_common ; 2,3,6,7,11,12,15,16,20,21,24,25,29,30,33,34-hexadecaethyl- 9,18,27, 36-tetraphenyl(32)octaphyrin-(1.0.1.0.1.0.1.0) ; _chemical_melting_point ? _chemical_formula_moiety 'C92 H104 N8 * 2(C4 H10 O)' _chemical_formula_sum 'C100 H124 N8 O2' _chemical_formula_weight 1470.07 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.381(2) _cell_length_b 19.5758(18) _cell_length_c 23.321(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.829(2) _cell_angle_gamma 90.00 _cell_volume 8806.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 5091 _cell_measurement_theta_min 2.278 _cell_measurement_theta_max 24.368 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3184 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'program SADABS ver. 2.03(Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 23466 _diffrn_reflns_av_R_equivalents 0.0834 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.24 _reflns_number_total 8797 _reflns_number_gt 4373 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT+ ver. 6.45' _computing_cell_refinement 'Bruker SAINT+ ver. 6.45' _computing_data_reduction 'Bruker SAINT+ ver. 6.45' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XSHELL ver. 4.02' _computing_publication_material 'Bruker SHELXTL ver. 6.14' _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. All hydrogen atoms were placed at ideal positions and included in the refinement. All the hydrogen atoms were allowed to ride on the immediately preceding atom X and, except for H50A, H50B, and H50C, allowed to rotate around the X-Y bond. The rotation around the C(49)-C(50) bond was prohibited because the positions of the methyl protons at C(50) did not come to convergence. Disorder was introduced into the O(1) atom and the site occupancies after the refinement were 0.64 and 0.36 for O(1A) and O(1B), respectively. All the non-hydrogen atoms except for O(1B), C(49), and C(50) of the diethyl ether solvate were refined anisotropically. ; _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^)+(0.1380P)^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 ? _refine_ls_number_reflns 8797 _refine_ls_number_parameters 500 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1518 _refine_ls_R_factor_gt 0.0781 _refine_ls_wR_factor_ref 0.2510 _refine_ls_wR_factor_gt 0.2045 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 N1 N 0.07112(12) 0.27404(11) 0.26038(11) 0.0514(6) Uani 1 1 d . . . H1N H 0.0523 0.2385 0.2400 0.062 Uiso 1 1 calc R . . N2 N 0.10042(11) 0.15426(11) 0.22484(10) 0.0493(6) Uani 1 1 d . . . N3 N 0.01046(11) 0.00270(11) 0.15405(9) 0.0467(6) Uani 1 1 d . . . H3N H 0.0280 -0.0285 0.1805 0.056 Uiso 1 1 calc R . . N4 N -0.02068(12) -0.11816(11) 0.18704(9) 0.0461(6) Uani 1 1 d . . . C1 C 0.03754(16) 0.33210(14) 0.26384(14) 0.0564(8) Uani 1 1 d . . . C2 C 0.08626(19) 0.37932(16) 0.30017(17) 0.0664(9) Uani 1 1 d . . . C3 C 0.14997(18) 0.34692(16) 0.32040(16) 0.0631(9) Uani 1 1 d . . . C4 C 0.14009(16) 0.27955(15) 0.29423(13) 0.0528(7) Uani 1 1 d . . . C5 C 0.18580(15) 0.22389(14) 0.29843(13) 0.0504(7) Uani 1 1 d . . . C6 C 0.16626(14) 0.16201(14) 0.26706(12) 0.0481(7) Uani 1 1 d . . . C7 C 0.20298(14) 0.09779(14) 0.27089(13) 0.0492(7) Uani 1 1 d . . . C8 C 0.15730(14) 0.05273(14) 0.23225(12) 0.0470(7) Uani 1 1 d . . . C9 C 0.09446(14) 0.08968(13) 0.20439(12) 0.0454(7) Uani 1 1 d . . . C10 C 0.03286(14) 0.06648(13) 0.15643(12) 0.0445(7) Uani 1 1 d . . . C11 C -0.00821(14) 0.10357(14) 0.10401(12) 0.0491(7) Uani 1 1 d . . . C12 C -0.05779(14) 0.05881(14) 0.06960(12) 0.0491(7) Uani 1 1 d . . . C13 C -0.04621(14) -0.00568(13) 0.10162(11) 0.0444(7) Uani 1 1 d . . . C14 C -0.08156(14) -0.06789(14) 0.08874(12) 0.0461(7) Uani 1 1 d . . . C15 C -0.06708(15) -0.12487(14) 0.12862(12) 0.0464(7) Uani 1 1 d . . . C16 C -0.09476(15) -0.19287(14) 0.12320(13) 0.0514(7) Uani 1 1 d . . . C17 C -0.06471(16) -0.22428(14) 0.17935(13) 0.0509(7) Uani 1 1 d . . . C18 C -0.01952(14) -0.17629(14) 0.21745(12) 0.0455(7) Uani 1 1 d . . . C19 C 0.0700(2) 0.45033(18) 0.3170(2) 0.0857(12) Uani 1 1 d . . . H19B H 0.1129 0.4721 0.3409 0.103 Uiso 1 1 calc R . . H19A H 0.0508 0.4768 0.2802 0.103 Uiso 1 1 calc R . . C20 C 0.0202(3) 0.4519(2) 0.3522(3) 0.134(2) Uani 1 1 d . . . H20A H -0.0217 0.4286 0.3298 0.201 Uiso 1 1 calc R . . H20C H 0.0096 0.4985 0.3587 0.201 Uiso 1 1 calc R . . H20B H 0.0406 0.4298 0.3906 0.201 Uiso 1 1 calc R . . C21 C 0.2125(2) 0.3774(2) 0.3663(2) 0.0932(13) Uani 1 1 d . . . H21A H 0.2155 0.4255 0.3575 0.112 Uiso 1 1 calc R . . H21B H 0.2539 0.3550 0.3639 0.112 Uiso 1 1 calc R . . C22 C 0.2084(2) 0.3694(3) 0.4307(2) 0.130(2) Uani 1 1 d . . . H22A H 0.1661 0.3894 0.4326 0.194 Uiso 1 1 calc R . . H22C H 0.2472 0.3920 0.4591 0.194 Uiso 1 1 calc R . . H22B H 0.2093 0.3217 0.4407 0.194 Uiso 1 1 calc R . . C23 C 0.27616(16) 0.07873(17) 0.30595(16) 0.0657(9) Uani 1 1 d . . . H23B H 0.2769 0.0323 0.3207 0.079 Uiso 1 1 calc R . . H23A H 0.2928 0.1085 0.3409 0.079 Uiso 1 1 calc R . . C24 C 0.3245(2) 0.0837(2) 0.2691(2) 0.1089(15) Uani 1 1 d . . . H24B H 0.3101 0.0522 0.2358 0.163 Uiso 1 1 calc R . . H24C H 0.3708 0.0727 0.2942 0.163 Uiso 1 1 calc R . . H24A H 0.3236 0.1293 0.2538 0.163 Uiso 1 1 calc R . . C25 C 0.17066(17) -0.02111(16) 0.22279(15) 0.0636(9) Uani 1 1 d . . . H25B H 0.1407 -0.0352 0.1831 0.076 Uiso 1 1 calc R . . H25A H 0.2183 -0.0262 0.2235 0.076 Uiso 1 1 calc R . . C26 C 0.1586(2) -0.06669(19) 0.26926(19) 0.0905(13) Uani 1 1 d . . . H26A H 0.1937 -0.0588 0.3076 0.136 Uiso 1 1 calc R . . H26C H 0.1605 -0.1135 0.2575 0.136 Uiso 1 1 calc R . . H26B H 0.1138 -0.0573 0.2728 0.136 Uiso 1 1 calc R . . C27 C 0.00098(17) 0.17756(15) 0.08928(14) 0.0610(8) Uani 1 1 d . . . H27B H 0.0486 0.1911 0.1100 0.073 Uiso 1 1 calc R . . H27A H -0.0074 0.1818 0.0461 0.073 Uiso 1 1 calc R . . C28 C -0.0465(2) 0.22499(19) 0.10719(18) 0.0895(13) Uani 1 1 d . . . H28A H -0.0937 0.2136 0.0851 0.134 Uiso 1 1 calc R . . H28C H -0.0373 0.2711 0.0981 0.134 Uiso 1 1 calc R . . H28B H -0.0389 0.2207 0.1499 0.134 Uiso 1 1 calc R . . C29 C -0.11012(16) 0.07781(16) 0.00951(13) 0.0592(8) Uani 1 1 d . . . H29B H -0.1256 0.1242 0.0120 0.071 Uiso 1 1 calc R . . H29A H -0.1501 0.0481 0.0019 0.071 Uiso 1 1 calc R . . C30 C -0.0828(2) 0.07288(19) -0.04360(14) 0.0763(10) Uani 1 1 d . . . H30B H -0.0455 0.1048 -0.0381 0.114 Uiso 1 1 calc R . . H30C H -0.1193 0.0833 -0.0804 0.114 Uiso 1 1 calc R . . H30A H -0.0662 0.0274 -0.0459 0.114 Uiso 1 1 calc R . . C31 C -0.1444(2) -0.22782(17) 0.06942(15) 0.0744(11) Uani 1 1 d . . . H31B H -0.1789 -0.1951 0.0469 0.089 Uiso 1 1 calc R . . H31A H -0.1683 -0.2638 0.0834 0.089 Uiso 1 1 calc R . . C32 C -0.1087(3) -0.2582(2) 0.0278(2) 0.1254(19) Uani 1 1 d . . . H32B H -0.0906 -0.2222 0.0093 0.188 Uiso 1 1 calc R . . H32C H -0.1413 -0.2847 -0.0031 0.188 Uiso 1 1 calc R . . H32A H -0.0713 -0.2871 0.0508 0.188 Uiso 1 1 calc R . . C33 C -0.08255(19) -0.29342(16) 0.19725(16) 0.0694(10) Uani 1 1 d . . . H33B H -0.1326 -0.2969 0.1854 0.083 Uiso 1 1 calc R . . H33A H -0.0646 -0.2968 0.2411 0.083 Uiso 1 1 calc R . . C34 C -0.0559(3) -0.35377(18) 0.1709(2) 0.1003(14) Uani 1 1 d . . . H34B H -0.0799 -0.3563 0.1281 0.151 Uiso 1 1 calc R . . H34C H -0.0637 -0.3950 0.1900 0.151 Uiso 1 1 calc R . . H34A H -0.0071 -0.3483 0.1778 0.151 Uiso 1 1 calc R . . C35 C 0.25879(16) 0.23113(16) 0.33950(15) 0.0594(8) Uani 1 1 d . . . C36 C 0.31054(18) 0.25322(18) 0.31759(18) 0.0767(10) Uani 1 1 d . . . H36 H 0.3000 0.2633 0.2766 0.092 Uiso 1 1 calc R . . C37 C 0.3781(2) 0.2605(2) 0.3563(3) 0.1012(15) Uani 1 1 d . . . H37 H 0.4124 0.2771 0.3416 0.121 Uiso 1 1 calc R . . C38 C 0.3942(3) 0.2430(3) 0.4166(3) 0.1197(19) Uani 1 1 d . . . H38 H 0.4396 0.2467 0.4423 0.144 Uiso 1 1 calc R . . C39 C 0.3449(3) 0.2208(3) 0.4381(2) 0.1154(17) Uani 1 1 d . . . H39 H 0.3563 0.2090 0.4787 0.138 Uiso 1 1 calc R . . C40 C 0.2763(2) 0.2149(2) 0.40022(18) 0.0864(12) Uani 1 1 d . . . H40 H 0.2422 0.2001 0.4160 0.104 Uiso 1 1 calc R . . C41 C -0.14011(15) -0.07507(14) 0.03033(12) 0.0508(7) Uani 1 1 d . . . C42 C -0.20750(17) -0.0680(2) 0.02864(16) 0.0757(10) Uani 1 1 d . . . H42 H -0.2171 -0.0593 0.0643 0.091 Uiso 1 1 calc R . . C43 C -0.2615(2) -0.0735(2) -0.0251(2) 0.0962(13) Uani 1 1 d . . . H43 H -0.3070 -0.0680 -0.0255 0.115 Uiso 1 1 calc R . . C44 C -0.2480(3) -0.0872(2) -0.07775(19) 0.0946(14) Uani 1 1 d . . . H44 H -0.2844 -0.0915 -0.1139 0.114 Uiso 1 1 calc R . . C45 C -0.1817(2) -0.0944(2) -0.07729(16) 0.0825(11) Uani 1 1 d . . . H45 H -0.1726 -0.1033 -0.1132 0.099 Uiso 1 1 calc R . . C46 C -0.12766(17) -0.08843(15) -0.02354(13) 0.0597(8) Uani 1 1 d . . . H46 H -0.0823 -0.0935 -0.0235 0.072 Uiso 1 1 calc R . . C47 C 0.3377(6) 0.8358(8) 0.3492(5) 0.269(7) Uani 1 1 d . . . H47A H 0.3828 0.8157 0.3546 0.322 Uiso 1 1 calc R A 1 H47B H 0.3206 0.8532 0.3082 0.322 Uiso 1 1 calc R A 1 C48 C 0.2886(4) 0.7774(4) 0.3542(2) 0.144(2) Uani 1 1 d . C . H48A H 0.3088 0.7533 0.3916 0.216 Uiso 1 1 calc R . . H48B H 0.2818 0.7464 0.3209 0.216 Uiso 1 1 calc R . . H48C H 0.2448 0.7962 0.3532 0.216 Uiso 1 1 calc R . . C49 C 0.3793(9) 0.9258(8) 0.4156(8) 0.288(8) Uiso 1 1 d . . . H49A H 0.4087 0.9331 0.3907 0.345 Uiso 1 1 calc R B 1 H49B H 0.4055 0.8941 0.4466 0.345 Uiso 1 1 calc R B 1 C50 C 0.3975(10) 1.0031(9) 0.4589(9) 0.413(10) Uiso 1 1 d . C . H50A H 0.4415 0.9991 0.4902 0.620 Uiso 1 1 calc R . . H50B H 0.3619 1.0109 0.4769 0.620 Uiso 1 1 calc R . . H50C H 0.3988 1.0406 0.4328 0.620 Uiso 1 1 calc R . . O1A O 0.3487(5) 0.8962(4) 0.3915(5) 0.166(5) Uani 0.64(2) 1 d P C 1 O1B O 0.3875(15) 0.8548(14) 0.3934(11) 0.218(12) Uiso 0.36(2) 1 d P C 2 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 N1 0.0565(15) 0.0385(13) 0.0587(15) -0.0080(11) 0.0178(12) -0.0077(11) N2 0.0495(14) 0.0402(13) 0.0520(14) -0.0060(10) 0.0077(11) -0.0064(10) N3 0.0504(14) 0.0410(13) 0.0386(13) 0.0032(10) 0.0003(11) -0.0024(10) N4 0.0549(14) 0.0418(13) 0.0360(12) 0.0011(10) 0.0068(11) -0.0020(10) C1 0.0714(19) 0.0385(16) 0.065(2) 0.0003(14) 0.0300(17) -0.0024(14) C2 0.080(2) 0.0457(18) 0.086(2) -0.0141(16) 0.044(2) -0.0175(17) C3 0.068(2) 0.0490(18) 0.082(2) -0.0147(16) 0.0372(18) -0.0185(16) C4 0.0538(18) 0.0487(17) 0.0583(18) -0.0088(14) 0.0216(15) -0.0154(14) C5 0.0484(16) 0.0484(17) 0.0557(18) -0.0053(13) 0.0186(14) -0.0132(14) C6 0.0467(16) 0.0447(16) 0.0491(16) -0.0048(13) 0.0101(13) -0.0078(13) C7 0.0464(16) 0.0522(17) 0.0462(16) 0.0029(13) 0.0112(13) -0.0046(13) C8 0.0495(16) 0.0472(16) 0.0412(15) -0.0011(12) 0.0102(13) -0.0002(13) C9 0.0488(16) 0.0436(16) 0.0404(15) -0.0011(12) 0.0098(13) -0.0017(13) C10 0.0453(15) 0.0397(15) 0.0433(16) -0.0008(12) 0.0069(12) -0.0010(12) C11 0.0484(16) 0.0455(16) 0.0480(17) 0.0013(13) 0.0082(13) 0.0044(13) C12 0.0461(16) 0.0502(16) 0.0441(16) 0.0015(13) 0.0048(13) 0.0026(13) C13 0.0446(15) 0.0451(16) 0.0389(15) -0.0007(12) 0.0072(12) -0.0021(12) C14 0.0453(16) 0.0510(17) 0.0390(15) -0.0040(12) 0.0094(12) -0.0039(13) C15 0.0496(16) 0.0466(16) 0.0395(15) -0.0056(12) 0.0095(13) -0.0068(13) C16 0.0597(18) 0.0441(16) 0.0484(17) -0.0056(13) 0.0147(14) -0.0105(14) C17 0.0595(18) 0.0420(15) 0.0485(17) -0.0059(13) 0.0138(14) -0.0073(13) C18 0.0534(17) 0.0395(15) 0.0428(14) -0.0025(12) 0.0146(13) 0.0010(13) C19 0.095(3) 0.053(2) 0.121(3) -0.027(2) 0.051(3) -0.0092(19) C20 0.174(5) 0.086(3) 0.180(5) -0.037(3) 0.110(5) -0.009(3) C21 0.073(3) 0.075(3) 0.135(4) -0.048(2) 0.039(3) -0.031(2) C22 0.087(3) 0.183(5) 0.111(4) -0.079(4) 0.020(3) -0.036(3) C23 0.0522(18) 0.061(2) 0.073(2) 0.0000(16) 0.0049(16) -0.0009(15) C24 0.075(3) 0.116(4) 0.140(4) -0.007(3) 0.041(3) -0.004(2) C25 0.0558(19) 0.0569(19) 0.068(2) -0.0099(16) 0.0052(16) 0.0043(15) C26 0.091(3) 0.062(2) 0.100(3) 0.015(2) 0.007(2) -0.004(2) C27 0.073(2) 0.0512(18) 0.0529(18) 0.0058(14) 0.0117(16) 0.0034(16) C28 0.106(3) 0.069(2) 0.081(3) -0.0103(19) 0.013(2) 0.021(2) C29 0.0569(18) 0.0550(18) 0.0531(18) 0.0022(14) 0.0002(15) 0.0062(14) C30 0.082(2) 0.085(2) 0.0486(19) 0.0113(17) 0.0022(17) 0.0012(19) C31 0.094(3) 0.057(2) 0.057(2) -0.0069(16) 0.0034(19) -0.0258(18) C32 0.188(5) 0.106(4) 0.075(3) -0.033(3) 0.032(3) -0.033(3) C33 0.079(2) 0.0512(19) 0.068(2) 0.0057(16) 0.0100(18) -0.0120(17) C34 0.132(4) 0.050(2) 0.105(3) -0.011(2) 0.019(3) -0.011(2) C35 0.0513(18) 0.062(2) 0.062(2) -0.0160(16) 0.0133(15) -0.0128(15) C36 0.062(2) 0.077(2) 0.093(3) -0.019(2) 0.027(2) -0.0206(18) C37 0.061(3) 0.104(3) 0.139(5) -0.046(3) 0.033(3) -0.024(2) C38 0.064(3) 0.140(5) 0.131(5) -0.057(4) -0.001(3) -0.012(3) C39 0.097(4) 0.142(4) 0.081(3) -0.028(3) -0.008(3) -0.003(3) C40 0.078(3) 0.105(3) 0.066(3) -0.021(2) 0.010(2) -0.020(2) C41 0.0519(18) 0.0520(17) 0.0414(17) 0.0013(13) 0.0050(13) -0.0103(14) C42 0.053(2) 0.109(3) 0.055(2) 0.0006(19) 0.0046(16) -0.0120(19) C43 0.053(2) 0.127(4) 0.092(3) 0.011(3) -0.001(2) -0.021(2) C44 0.087(3) 0.115(3) 0.056(2) 0.007(2) -0.012(2) -0.034(3) C45 0.097(3) 0.093(3) 0.047(2) -0.0078(18) 0.009(2) -0.023(2) C46 0.067(2) 0.064(2) 0.0407(17) -0.0044(14) 0.0083(15) -0.0108(16) C47 0.171(9) 0.44(2) 0.165(8) -0.080(11) 0.017(8) 0.040(11) C48 0.148(5) 0.190(6) 0.070(3) 0.026(3) 0.001(3) -0.035(4) O1A 0.130(7) 0.119(7) 0.214(9) -0.040(5) 0.007(5) 0.005(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 N1 C1 1.343(4) . ? N1 C4 1.376(4) . ? N2 C9 1.343(3) . ? N2 C6 1.393(3) . ? N3 C10 1.324(3) . ? N3 C13 1.394(3) . ? N4 C18 1.337(3) . ? N4 C15 1.392(3) . ? C1 C2 1.420(4) . ? C1 C1 1.456(6) 2 ? C2 C3 1.384(5) . ? C2 C19 1.510(5) . ? C3 C4 1.440(4) . ? C3 C21 1.499(5) . ? C4 C5 1.416(4) . ? C5 C6 1.404(4) . ? C5 C35 1.494(4) . ? C6 C7 1.451(4) . ? C7 C8 1.384(4) . ? C7 C23 1.498(4) . ? C8 C9 1.431(4) . ? C8 C25 1.500(4) . ? C9 C10 1.458(4) . ? C10 C11 1.436(4) . ? C11 C12 1.382(4) . ? C11 C27 1.514(4) . ? C12 C13 1.447(4) . ? C12 C29 1.508(4) . ? C13 C14 1.397(4) . ? C14 C15 1.421(4) . ? C14 C41 1.500(4) . ? C15 C16 1.435(4) . ? C16 C17 1.397(4) . ? C16 C31 1.498(4) . ? C17 C18 1.412(4) . ? C17 C33 1.495(4) . ? C18 C18 1.469(5) 2 ? C19 C20 1.498(6) . ? C21 C22 1.539(7) . ? C23 C24 1.506(6) . ? C25 C26 1.484(5) . ? C27 C28 1.495(5) . ? C29 C30 1.516(5) . ? C31 C32 1.510(6) . ? C33 C34 1.512(5) . ? C35 C40 1.381(5) . ? C35 C36 1.382(5) . ? C36 C37 1.389(5) . ? C37 C38 1.381(7) . ? C38 C39 1.332(7) . ? C39 C40 1.397(6) . ? C41 C42 1.368(4) . ? C41 C46 1.384(4) . ? C42 C43 1.380(5) . ? C43 C44 1.369(6) . ? C44 C45 1.354(6) . ? C45 C46 1.381(4) . ? C47 O1B 1.25(2) . ? C47 O1A 1.509(14) . ? C47 C48 1.548(14) . ? C49 O1A 0.903(15) . ? C49 O1B 1.51(3) . ? C49 C50 1.789(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 110.2(2) . . ? C9 N2 C6 108.0(2) . . ? C10 N3 C13 108.9(2) . . ? C18 N4 C15 109.2(2) . . ? N1 C1 C2 108.4(3) . . ? N1 C1 C1 117.15(19) . 2 ? C2 C1 C1 134.2(2) . 2 ? C3 C2 C1 107.7(3) . . ? C3 C2 C19 126.4(3) . . ? C1 C2 C19 125.8(3) . . ? C2 C3 C4 106.7(3) . . ? C2 C3 C21 123.3(3) . . ? C4 C3 C21 129.7(3) . . ? N1 C4 C5 120.4(2) . . ? N1 C4 C3 107.0(3) . . ? C5 C4 C3 132.6(3) . . ? C6 C5 C4 123.9(3) . . ? C6 C5 C35 118.2(3) . . ? C4 C5 C35 117.9(2) . . ? N2 C6 C5 120.6(3) . . ? N2 C6 C7 108.0(2) . . ? C5 C6 C7 131.4(3) . . ? C8 C7 C6 106.7(2) . . ? C8 C7 C23 122.6(3) . . ? C6 C7 C23 130.7(3) . . ? C7 C8 C9 106.8(2) . . ? C7 C8 C25 126.4(3) . . ? C9 C8 C25 126.8(2) . . ? N2 C9 C8 110.5(2) . . ? N2 C9 C10 121.5(2) . . ? C8 C9 C10 127.8(2) . . ? N3 C10 C11 110.0(2) . . ? N3 C10 C9 121.7(2) . . ? C11 C10 C9 128.1(2) . . ? C12 C11 C10 106.9(2) . . ? C12 C11 C27 126.6(2) . . ? C10 C11 C27 126.6(2) . . ? C11 C12 C13 106.7(2) . . ? C11 C12 C29 123.3(3) . . ? C13 C12 C29 130.0(3) . . ? N3 C13 C14 121.0(2) . . ? N3 C13 C12 107.5(2) . . ? C14 C13 C12 131.5(2) . . ? C13 C14 C15 124.0(2) . . ? C13 C14 C41 118.7(2) . . ? C15 C14 C41 117.2(2) . . ? N4 C15 C14 119.9(2) . . ? N4 C15 C16 107.3(2) . . ? C14 C15 C16 132.7(2) . . ? C17 C16 C15 106.6(2) . . ? C17 C16 C31 123.8(3) . . ? C15 C16 C31 129.6(3) . . ? C16 C17 C18 107.3(2) . . ? C16 C17 C33 126.0(3) . . ? C18 C17 C33 126.5(3) . . ? N4 C18 C17 109.6(2) . . ? N4 C18 C18 117.33(16) . 2 ? C17 C18 C18 132.6(2) . 2 ? C20 C19 C2 114.0(3) . . ? C3 C21 C22 110.8(3) . . ? C7 C23 C24 113.1(3) . . ? C26 C25 C8 113.0(3) . . ? C28 C27 C11 113.1(3) . . ? C12 C29 C30 114.0(3) . . ? C16 C31 C32 112.5(3) . . ? C17 C33 C34 116.2(3) . . ? C40 C35 C36 118.4(3) . . ? C40 C35 C5 120.6(3) . . ? C36 C35 C5 120.9(3) . . ? C35 C36 C37 120.5(4) . . ? C38 C37 C36 119.7(4) . . ? C39 C38 C37 120.3(4) . . ? C38 C39 C40 120.8(5) . . ? C35 C40 C39 120.2(4) . . ? C42 C41 C46 118.0(3) . . ? C42 C41 C14 120.9(3) . . ? C46 C41 C14 121.1(3) . . ? C41 C42 C43 121.2(4) . . ? C44 C43 C42 119.8(4) . . ? C45 C44 C43 120.1(4) . . ? C44 C45 C46 120.0(4) . . ? C45 C46 C41 120.9(3) . . ? O1B C47 O1A 46.9(14) . . ? O1B C47 C48 122.2(14) . . ? O1A C47 C48 119.5(9) . . ? O1A C49 O1B 47.6(12) . . ? O1A C49 C50 150.5(18) . . ? O1B C49 C50 160.9(16) . . ? C49 O1A C47 146.8(15) . . ? C47 O1B C49 114(2) . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 27.24 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 0.347 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.053