# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Darren J. Dixon' 'A. Louise Tillman' 'Jinxing Ye.' _publ_contact_author_name 'Darren J. Dixon' _publ_contact_author_address ; School of Chemistry The University of Manchester Oxford Road Manchester M13 9PL UK ; _publ_contact_author_email DARREN.DIXON@MANCHESTER.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Direct Enantio- and Diastereoselective Mannich Reactions of Malonate and a-Keto Esters with N-Boc- and N-Cbz-Aldimines Catalysed by a Bifunctional Cinchonine Derivative ; data_dd0504 _database_code_depnum_ccdc_archive 'CCDC 289062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 N O5' _chemical_formula_sum 'C23 H27 N O5' _chemical_formula_weight 397.46 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.8665(3) _cell_length_b 11.1927(3) _cell_length_c 34.5493(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4202.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 49452 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 22.46 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.641 _exptl_absorpt_correction_T_max 1.040 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Poor (small) crystal. Poor data, hence relatively high R-factors. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 15361 _diffrn_reflns_av_R_equivalents 0.1360 _diffrn_reflns_av_sigmaI/netI 0.1291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 22.46 _reflns_number_total 5309 _reflns_number_gt 3458 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0598P)^2^+4.7893P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 5309 _refine_ls_number_parameters 531 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1389 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.1881 _refine_ls_wR_factor_gt 0.1604 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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_1 N 0.2786(6) -0.8751(5) 0.59800(16) 0.0474(16) Uani 1 1 d . . . H1_1 H 0.2877 -0.9440 0.5861 0.057 Uiso 1 1 calc R . . O1_1 O 0.4572(5) -0.2235(4) 0.54356(14) 0.0576(15) Uani 1 1 d . . . O2_1 O 0.3383(5) -0.1597(4) 0.59195(14) 0.0470(14) Uani 1 1 d . . . O3_1 O 0.2176(6) -0.4124(5) 0.54502(15) 0.0622(15) Uani 1 1 d . . . O4_1 O 0.1046(5) -0.5133(4) 0.63728(15) 0.0504(13) Uani 1 1 d . . . O5_1 O 0.0107(4) -0.3321(4) 0.63376(12) 0.0404(12) Uani 1 1 d . . . C1_1 C 0.4600(8) -0.1023(6) 0.5280(2) 0.064(3) Uani 1 1 d . . . H1A_1 H 0.5174 -0.0989 0.5061 0.097 Uiso 1 1 calc R . . H1B_1 H 0.4871 -0.0467 0.5482 0.097 Uiso 1 1 calc R . . H1C_1 H 0.3774 -0.0799 0.5192 0.097 Uiso 1 1 calc R . . C2_1 C 0.3922(8) -0.2397(7) 0.57589(19) 0.0414(18) Uani 1 1 d . . . C3_1 C 0.3946(6) -0.3709(5) 0.58728(17) 0.0328(16) Uani 1 1 d . . . C4_1 C 0.5236(7) -0.4280(6) 0.58506(19) 0.045(2) Uani 1 1 d . . . H4A_1 H 0.5876 -0.3650 0.5856 0.054 Uiso 1 1 calc R . . H4B_1 H 0.5367 -0.4816 0.6075 0.054 Uiso 1 1 calc R . . C5_1 C 0.5318(9) -0.4981(8) 0.5477(2) 0.066(2) Uani 1 1 d . . . H5A_1 H 0.5898 -0.5659 0.5502 0.079 Uiso 1 1 calc R . . H5B_1 H 0.5581 -0.4466 0.5260 0.079 Uiso 1 1 calc R . . C6_1 C 0.3978(9) -0.5424(6) 0.5422(2) 0.059(2) Uani 1 1 d . . . H6A_1 H 0.3810 -0.5603 0.5146 0.070 Uiso 1 1 calc R . . H6B_1 H 0.3821 -0.6152 0.5577 0.070 Uiso 1 1 calc R . . C7_1 C 0.3203(8) -0.4403(6) 0.5560(2) 0.043(2) Uani 1 1 d . . . C8_1 C 0.3324(6) -0.3957(6) 0.62761(17) 0.0324(17) Uani 1 1 d . . . H8_1 H 0.3181 -0.4839 0.6289 0.039 Uiso 1 1 calc R . . C9_1 C 0.4158(6) -0.3655(6) 0.66136(18) 0.0361(18) Uani 1 1 d . . . C10_1 C 0.4686(6) -0.4543(6) 0.68163(18) 0.0388(18) Uani 1 1 d . . . H10_1 H 0.4501 -0.5347 0.6750 0.047 Uiso 1 1 calc R . . C11_1 C 0.4412(7) -0.2449(6) 0.67156(19) 0.0424(19) Uani 1 1 d . . . H11_1 H 0.4029 -0.1819 0.6576 0.051 Uiso 1 1 calc R . . C12_1 C 0.5205(7) -0.2188(6) 0.70131(19) 0.045(2) Uani 1 1 d . . . H12_1 H 0.5372 -0.1377 0.7076 0.054 Uiso 1 1 calc R . . C13_1 C 0.5771(6) -0.3105(6) 0.72265(19) 0.0397(18) Uani 1 1 d . . . C14_1 C 0.5525(6) -0.4315(6) 0.7132(2) 0.0384(18) Uani 1 1 d . . . C15_1 C 0.6100(7) -0.5223(7) 0.7344(2) 0.051(2) Uani 1 1 d . . . H15_1 H 0.5931 -0.6033 0.7282 0.061 Uiso 1 1 calc R . . C16_1 C 0.6905(7) -0.4965(8) 0.7640(2) 0.056(2) Uani 1 1 d . . . H16_1 H 0.7290 -0.5595 0.7780 0.067 Uiso 1 1 calc R . . C17_1 C 0.7159(8) -0.3765(8) 0.7737(2) 0.058(2) Uani 1 1 d . . . H17_1 H 0.7724 -0.3587 0.7938 0.069 Uiso 1 1 calc R . . C18_1 C 0.6593(7) -0.2859(7) 0.75411(19) 0.048(2) Uani 1 1 d . . . H18_1 H 0.6746 -0.2055 0.7614 0.057 Uiso 1 1 calc R . . C19_1 C 0.1087(7) -0.4065(7) 0.63423(18) 0.0359(17) Uani 1 1 d . . . C20_1 C -0.1156(7) -0.3752(7) 0.6420(2) 0.058(2) Uani 1 1 d . . . C21_1 C -0.1547(10) -0.4651(10) 0.6132(5) 0.174(8) Uani 1 1 d . . . H21A_1 H -0.1321 -0.4378 0.5872 0.262 Uiso 1 1 calc R . . H21B_1 H -0.2441 -0.4757 0.6146 0.262 Uiso 1 1 calc R . . H21C_1 H -0.1139 -0.5413 0.6186 0.262 Uiso 1 1 calc R . . C22_1 C -0.1925(7) -0.2638(6) 0.6392(2) 0.056(2) Uani 1 1 d . . . H22A_1 H -0.1930 -0.2353 0.6124 0.084 Uiso 1 1 calc R . . H22B_1 H -0.1578 -0.2019 0.6560 0.084 Uiso 1 1 calc R . . H22C_1 H -0.2769 -0.2816 0.6474 0.084 Uiso 1 1 calc R . . C23_1 C -0.1118(10) -0.4211(10) 0.6844(3) 0.127(5) Uani 1 1 d . . . H23A_1 H -0.0757 -0.3595 0.7011 0.190 Uiso 1 1 calc R . . H23B_1 H -0.0617 -0.4938 0.6858 0.190 Uiso 1 1 calc R . . H23C_1 H -0.1956 -0.4389 0.6932 0.190 Uiso 1 1 calc R . . N1_2 N 0.2130(5) -0.3407(5) 0.63095(16) 0.0402(15) Uani 1 1 d . . . H1_2 H 0.2076 -0.2622 0.6309 0.048 Uiso 1 1 calc R . . O1_2 O 0.1187(6) -1.0391(5) 0.55338(15) 0.0636(16) Uani 1 1 d . . . O2_2 O -0.0796(7) -0.9862(6) 0.55658(18) 0.078(2) Uani 1 1 d . . . O3_2 O 0.2417(7) -0.8419(5) 0.51492(16) 0.083(2) Uani 1 1 d . . . O4_2 O 0.3773(5) -0.7229(4) 0.62764(15) 0.0578(15) Uani 1 1 d . . . O5_2 O 0.4794(5) -0.8908(5) 0.60729(15) 0.0590(15) Uani 1 1 d . . . C1_2 C 0.0663(12) -1.1613(8) 0.5491(3) 0.112(5) Uani 1 1 d . . . H1A_2 H 0.1231 -1.2110 0.5341 0.169 Uiso 1 1 calc R . . H1B_2 H -0.0130 -1.1566 0.5357 0.169 Uiso 1 1 calc R . . H1C_2 H 0.0543 -1.1967 0.5748 0.169 Uiso 1 1 calc R . . C2_2 C 0.0280(12) -0.9599(8) 0.5580(2) 0.064(3) Uani 1 1 d . . . C3_2 C 0.0766(7) -0.8346(6) 0.56369(19) 0.046(2) Uani 1 1 d . . . C4_2 C -0.0338(8) -0.7464(7) 0.5643(2) 0.064(2) Uani 1 1 d . . . H4A_2 H -0.1073 -0.7834 0.5523 0.077 Uiso 1 1 calc R . . H4B_2 H -0.0541 -0.7231 0.5912 0.077 Uiso 1 1 calc R . . C5_2 C 0.0062(11) -0.6427(9) 0.5419(3) 0.103(4) Uani 1 1 d . . . H5A_2 H 0.0482 -0.5847 0.5591 0.123 Uiso 1 1 calc R . . H5B_2 H -0.0659 -0.6027 0.5301 0.123 Uiso 1 1 calc R . . C6_2 C 0.0930(8) -0.6846(6) 0.5109(2) 0.057(2) Uani 1 1 d . . . H6A_2 H 0.0479 -0.7034 0.4867 0.068 Uiso 1 1 calc R . . H6B_2 H 0.1561 -0.6232 0.5053 0.068 Uiso 1 1 calc R . . C7_2 C 0.1508(8) -0.7952(7) 0.5277(2) 0.051(2) Uani 1 1 d . . . C8_2 C 0.1553(7) -0.8230(6) 0.60132(19) 0.0414(19) Uani 1 1 d . . . H8_2 H 0.1666 -0.7357 0.6063 0.050 Uiso 1 1 calc R . . C9_2 C 0.0891(6) -0.8740(6) 0.63615(18) 0.0357(17) Uani 1 1 d . . . C10_2 C 0.0210(6) -0.8025(6) 0.66066(18) 0.0377(18) Uani 1 1 d . . . H10_2 H 0.0160 -0.7193 0.6553 0.045 Uiso 1 1 calc R . . C11_2 C 0.0944(7) -0.9979(6) 0.6451(2) 0.0422(18) Uani 1 1 d . . . H11_2 H 0.1411 -1.0490 0.6288 0.051 Uiso 1 1 calc R . . C12_2 C 0.0359(7) -1.0455(6) 0.67574(19) 0.0436(19) Uani 1 1 d . . . H12_2 H 0.0423 -1.1288 0.6807 0.052 Uiso 1 1 calc R . . C13_2 C -0.0344(7) -0.9738(6) 0.70042(18) 0.0393(18) Uani 1 1 d . . . C14_2 C -0.0409(7) -0.8475(6) 0.6930(2) 0.0399(18) Uani 1 1 d . . . C15_2 C -0.1123(8) -0.7773(7) 0.7188(2) 0.054(2) Uani 1 1 d . . . H15_2 H -0.1169 -0.6935 0.7146 0.064 Uiso 1 1 calc R . . C16_2 C -0.1760(8) -0.8261(8) 0.7499(2) 0.061(2) Uani 1 1 d . . . H16_2 H -0.2248 -0.7767 0.7662 0.074 Uiso 1 1 calc R . . C17_2 C -0.1673(8) -0.9480(8) 0.7568(2) 0.060(2) Uani 1 1 d . . . H17_2 H -0.2083 -0.9810 0.7786 0.073 Uiso 1 1 calc R . . C18_2 C -0.1009(7) -1.0218(7) 0.7330(2) 0.051(2) Uani 1 1 d . . . H18_2 H -0.0987 -1.1052 0.7380 0.061 Uiso 1 1 calc R . . C19_2 C 0.3767(8) -0.8209(8) 0.6125(2) 0.049(2) Uani 1 1 d . . . C20_2 C 0.5917(6) -0.8683(6) 0.6284(2) 0.0441(19) Uani 1 1 d . . . C21_2 C 0.6528(7) -0.7552(7) 0.6148(3) 0.068(3) Uani 1 1 d . . . H21A_2 H 0.5942 -0.6888 0.6163 0.102 Uiso 1 1 calc R . . H21B_2 H 0.6800 -0.7651 0.5879 0.102 Uiso 1 1 calc R . . H21C_2 H 0.7241 -0.7379 0.6312 0.102 Uiso 1 1 calc R . . C22_2 C 0.6719(8) -0.9752(8) 0.6169(3) 0.083(3) Uani 1 1 d . . . H22A_2 H 0.6301 -1.0496 0.6241 0.124 Uiso 1 1 calc R . . H22B_2 H 0.7511 -0.9704 0.6304 0.124 Uiso 1 1 calc R . . H22C_2 H 0.6859 -0.9740 0.5889 0.124 Uiso 1 1 calc R . . C23_2 C 0.5684(9) -0.8666(8) 0.6711(2) 0.076(3) Uani 1 1 d . . . H23A_2 H 0.5121 -0.8011 0.6774 0.115 Uiso 1 1 calc R . . H23B_2 H 0.6464 -0.8550 0.6849 0.115 Uiso 1 1 calc R . . H23C_2 H 0.5315 -0.9427 0.6791 0.115 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 N1_1 0.052(5) 0.034(4) 0.056(4) -0.014(3) 0.003(4) -0.003(4) O1_1 0.081(4) 0.042(3) 0.050(3) 0.003(3) 0.025(3) -0.012(3) O2_1 0.057(4) 0.034(3) 0.050(3) 0.001(3) 0.014(3) 0.004(3) O3_1 0.064(4) 0.063(4) 0.060(3) -0.011(3) -0.014(3) -0.007(3) O4_1 0.042(3) 0.030(3) 0.079(4) 0.008(3) 0.001(3) -0.001(3) O5_1 0.034(3) 0.038(3) 0.049(3) 0.005(2) 0.006(2) 0.004(3) C1_1 0.092(7) 0.039(5) 0.062(5) 0.007(4) 0.043(5) -0.002(5) C2_1 0.048(5) 0.049(5) 0.027(4) -0.003(4) -0.005(4) -0.021(5) C3_1 0.031(4) 0.031(4) 0.037(4) -0.002(3) 0.010(4) 0.004(4) C4_1 0.040(5) 0.057(5) 0.038(4) -0.001(4) 0.013(4) 0.014(4) C5_1 0.072(7) 0.082(6) 0.045(5) 0.003(4) 0.004(5) 0.031(6) C6_1 0.093(7) 0.044(5) 0.039(4) -0.015(4) 0.003(5) 0.016(5) C7_1 0.057(5) 0.036(5) 0.037(4) 0.003(4) 0.007(4) -0.013(4) C8_1 0.034(4) 0.028(4) 0.035(4) 0.004(3) 0.010(4) -0.008(3) C9_1 0.035(5) 0.038(5) 0.034(4) -0.004(4) 0.008(4) -0.001(4) C10_1 0.036(4) 0.048(5) 0.032(4) 0.002(4) 0.007(4) 0.002(4) C11_1 0.053(5) 0.046(5) 0.028(4) -0.003(4) 0.006(4) 0.004(4) C12_1 0.066(6) 0.036(4) 0.032(4) -0.006(4) 0.004(4) -0.001(4) C13_1 0.040(5) 0.047(5) 0.032(4) 0.001(4) 0.010(4) -0.002(4) C14_1 0.030(4) 0.043(5) 0.041(4) 0.010(4) 0.012(4) 0.005(4) C15_1 0.050(5) 0.059(5) 0.044(4) 0.003(4) 0.011(5) -0.009(5) C16_1 0.057(6) 0.062(6) 0.048(5) 0.016(4) -0.003(5) 0.000(5) C17_1 0.062(6) 0.069(6) 0.042(5) 0.008(5) -0.008(4) 0.004(5) C18_1 0.050(5) 0.058(5) 0.036(4) 0.001(4) 0.004(4) 0.002(4) C19_1 0.036(5) 0.043(5) 0.028(4) 0.001(3) -0.004(4) 0.005(4) C20_1 0.032(5) 0.055(5) 0.087(6) -0.004(5) -0.005(5) -0.013(4) C21_1 0.066(8) 0.116(9) 0.34(2) -0.161(12) -0.083(10) 0.048(7) C22_1 0.041(5) 0.038(4) 0.090(6) -0.008(4) 0.004(5) 0.014(4) C23_1 0.066(7) 0.169(12) 0.146(11) 0.092(9) 0.051(8) 0.043(8) N1_2 0.034(4) 0.026(3) 0.061(4) -0.003(3) 0.008(3) 0.002(3) O1_2 0.095(5) 0.038(3) 0.057(3) -0.009(3) -0.015(3) 0.002(3) O2_2 0.082(5) 0.080(4) 0.072(4) 0.002(3) -0.004(4) -0.025(4) O3_2 0.098(5) 0.087(4) 0.065(4) 0.003(3) 0.031(4) 0.030(4) O4_2 0.061(4) 0.042(3) 0.071(3) -0.015(3) -0.009(3) -0.001(3) O5_2 0.039(3) 0.060(3) 0.078(4) -0.019(3) 0.001(3) -0.002(3) C1_2 0.206(14) 0.066(6) 0.066(6) -0.004(5) -0.024(8) -0.025(7) C2_2 0.106(9) 0.063(7) 0.023(4) 0.009(4) -0.008(6) -0.002(7) C3_2 0.066(6) 0.038(5) 0.033(4) 0.004(3) 0.004(4) 0.005(4) C4_2 0.079(7) 0.056(5) 0.057(5) 0.015(4) -0.012(5) 0.010(5) C5_2 0.110(9) 0.097(8) 0.101(8) 0.052(7) 0.011(7) 0.038(7) C6_2 0.074(6) 0.057(5) 0.040(4) 0.001(4) -0.006(5) -0.003(5) C7_2 0.061(6) 0.051(5) 0.042(4) 0.002(4) 0.003(5) 0.005(5) C8_2 0.046(5) 0.032(4) 0.046(4) -0.001(3) 0.007(4) 0.006(4) C9_2 0.037(5) 0.039(4) 0.030(4) -0.003(3) -0.004(4) -0.001(4) C10_2 0.048(5) 0.035(4) 0.031(4) -0.001(3) -0.004(4) -0.005(4) C11_2 0.049(5) 0.034(4) 0.043(4) -0.003(3) -0.002(4) -0.002(4) C12_2 0.053(5) 0.042(4) 0.036(4) 0.002(4) 0.000(4) 0.004(4) C13_2 0.038(4) 0.049(5) 0.031(4) -0.003(4) 0.004(4) -0.010(4) C14_2 0.042(5) 0.039(5) 0.040(4) -0.002(4) 0.001(4) -0.001(4) C15_2 0.068(6) 0.042(4) 0.051(5) -0.005(4) -0.002(5) 0.018(5) C16_2 0.071(6) 0.061(6) 0.052(5) 0.003(5) 0.024(5) 0.002(5) C17_2 0.066(6) 0.077(7) 0.039(4) 0.008(5) 0.008(5) -0.015(5) C18_2 0.049(5) 0.055(5) 0.048(5) 0.005(4) 0.008(4) -0.003(5) C19_2 0.047(6) 0.052(5) 0.048(5) -0.003(4) 0.009(4) -0.002(5) C20_2 0.027(5) 0.041(4) 0.064(5) 0.005(4) -0.006(4) 0.011(4) C21_2 0.046(6) 0.061(6) 0.097(7) 0.006(5) 0.002(5) -0.007(5) C22_2 0.065(6) 0.066(6) 0.117(8) -0.014(6) -0.020(6) 0.012(5) C23_2 0.077(7) 0.090(7) 0.062(6) 0.015(5) 0.003(5) -0.003(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1_1 C19_2 1.325(9) . ? N1_1 C8_2 1.465(9) . ? N1_1 H1_1 0.8800 . ? O1_1 C2_1 1.334(8) . ? O1_1 C1_1 1.460(8) . ? O2_1 C2_1 1.205(8) . ? O3_1 C7_1 1.219(9) . ? O4_1 C19_1 1.201(8) . ? O5_1 C19_1 1.352(8) . ? O5_1 C20_1 1.483(9) . ? C1_1 H1A_1 0.9800 . ? C1_1 H1B_1 0.9800 . ? C1_1 H1C_1 0.9800 . ? C2_1 C3_1 1.521(9) . ? C3_1 C4_1 1.542(9) . ? C3_1 C7_1 1.557(10) . ? C3_1 C8_1 1.574(8) . ? C4_1 C5_1 1.512(9) . ? C4_1 H4A_1 0.9900 . ? C4_1 H4B_1 0.9900 . ? C5_1 C6_1 1.551(11) . ? C5_1 H5A_1 0.9900 . ? C5_1 H5B_1 0.9900 . ? C6_1 C7_1 1.499(10) . ? C6_1 H6A_1 0.9900 . ? C6_1 H6B_1 0.9900 . ? C8_1 N1_2 1.440(8) . ? C8_1 C9_1 1.515(9) . ? C8_1 H8_1 1.0000 . ? C9_1 C10_1 1.344(9) . ? C9_1 C11_1 1.422(9) . ? C10_1 C14_1 1.446(9) . ? C10_1 H10_1 0.9500 . ? C11_1 C12_1 1.373(9) . ? C11_1 H11_1 0.9500 . ? C12_1 C13_1 1.405(9) . ? C12_1 H12_1 0.9500 . ? C13_1 C14_1 1.419(9) . ? C13_1 C18_1 1.433(10) . ? C14_1 C15_1 1.399(10) . ? C15_1 C16_1 1.378(10) . ? C15_1 H15_1 0.9500 . ? C16_1 C17_1 1.412(11) . ? C16_1 H16_1 0.9500 . ? C17_1 C18_1 1.365(10) . ? C17_1 H17_1 0.9500 . ? C18_1 H18_1 0.9500 . ? C19_1 N1_2 1.357(9) . ? C20_1 C21_1 1.477(12) . ? C20_1 C22_1 1.504(10) . ? C20_1 C23_1 1.555(12) . ? C21_1 H21A_1 0.9800 . ? C21_1 H21B_1 0.9800 . ? C21_1 H21C_1 0.9800 . ? C22_1 H22A_1 0.9800 . ? C22_1 H22B_1 0.9800 . ? C22_1 H22C_1 0.9800 . ? C23_1 H23A_1 0.9800 . ? C23_1 H23B_1 0.9800 . ? C23_1 H23C_1 0.9800 . ? N1_2 H1_2 0.8800 . ? O1_2 C2_2 1.335(11) . ? O1_2 C1_2 1.489(9) . ? O2_2 C2_2 1.207(11) . ? O3_2 C7_2 1.202(9) . ? O4_2 C19_2 1.215(9) . ? O5_2 C19_2 1.374(9) . ? O5_2 C20_2 1.443(8) . ? C1_2 H1A_2 0.9800 . ? C1_2 H1B_2 0.9800 . ? C1_2 H1C_2 0.9800 . ? C2_2 C3_2 1.512(11) . ? C3_2 C7_2 1.546(10) . ? C3_2 C4_2 1.553(10) . ? C3_2 C8_2 1.562(10) . ? C4_2 C5_2 1.460(11) . ? C4_2 H4A_2 0.9900 . ? C4_2 H4B_2 0.9900 . ? C5_2 C6_2 1.504(12) . ? C5_2 H5A_2 0.9900 . ? C5_2 H5B_2 0.9900 . ? C6_2 C7_2 1.506(10) . ? C6_2 H6A_2 0.9900 . ? C6_2 H6B_2 0.9900 . ? C8_2 C9_2 1.514(9) . ? C8_2 H8_2 1.0000 . ? C9_2 C10_2 1.380(9) . ? C9_2 C11_2 1.422(9) . ? C10_2 C14_2 1.399(9) . ? C10_2 H10_2 0.9500 . ? C11_2 C12_2 1.344(9) . ? C11_2 H11_2 0.9500 . ? C12_2 C13_2 1.398(9) . ? C12_2 H12_2 0.9500 . ? C13_2 C14_2 1.439(9) . ? C13_2 C18_2 1.441(9) . ? C14_2 C15_2 1.418(9) . ? C15_2 C16_2 1.391(10) . ? C15_2 H15_2 0.9500 . ? C16_2 C17_2 1.388(11) . ? C16_2 H16_2 0.9500 . ? C17_2 C18_2 1.372(10) . ? C17_2 H17_2 0.9500 . ? C18_2 H18_2 0.9500 . ? C20_2 C23_2 1.498(10) . ? C20_2 C21_2 1.506(10) . ? C20_2 C22_2 1.533(10) . ? C21_2 H21A_2 0.9800 . ? C21_2 H21B_2 0.9800 . ? C21_2 H21C_2 0.9800 . ? C22_2 H22A_2 0.9800 . ? C22_2 H22B_2 0.9800 . ? C22_2 H22C_2 0.9800 . ? C23_2 H23A_2 0.9800 . ? C23_2 H23B_2 0.9800 . ? C23_2 H23C_2 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19_2 N1_1 C8_2 121.6(6) . . ? C19_2 N1_1 H1_1 119.2 . . ? C8_2 N1_1 H1_1 119.2 . . ? C2_1 O1_1 C1_1 116.5(6) . . ? C19_1 O5_1 C20_1 121.8(6) . . ? O1_1 C1_1 H1A_1 109.5 . . ? O1_1 C1_1 H1B_1 109.5 . . ? H1A_1 C1_1 H1B_1 109.5 . . ? O1_1 C1_1 H1C_1 109.5 . . ? H1A_1 C1_1 H1C_1 109.5 . . ? H1B_1 C1_1 H1C_1 109.5 . . ? O2_1 C2_1 O1_1 122.9(6) . . ? O2_1 C2_1 C3_1 127.3(6) . . ? O1_1 C2_1 C3_1 109.8(7) . . ? C2_1 C3_1 C4_1 113.7(6) . . ? C2_1 C3_1 C7_1 107.0(5) . . ? C4_1 C3_1 C7_1 103.3(5) . . ? C2_1 C3_1 C8_1 113.1(5) . . ? C4_1 C3_1 C8_1 111.2(5) . . ? C7_1 C3_1 C8_1 107.7(5) . . ? C5_1 C4_1 C3_1 108.1(6) . . ? C5_1 C4_1 H4A_1 110.1 . . ? C3_1 C4_1 H4A_1 110.1 . . ? C5_1 C4_1 H4B_1 110.1 . . ? C3_1 C4_1 H4B_1 110.1 . . ? H4A_1 C4_1 H4B_1 108.4 . . ? C4_1 C5_1 C6_1 102.5(6) . . ? C4_1 C5_1 H5A_1 111.3 . . ? C6_1 C5_1 H5A_1 111.3 . . ? C4_1 C5_1 H5B_1 111.3 . . ? C6_1 C5_1 H5B_1 111.3 . . ? H5A_1 C5_1 H5B_1 109.2 . . ? C7_1 C6_1 C5_1 104.1(6) . . ? C7_1 C6_1 H6A_1 110.9 . . ? C5_1 C6_1 H6A_1 110.9 . . ? C7_1 C6_1 H6B_1 110.9 . . ? C5_1 C6_1 H6B_1 110.9 . . ? H6A_1 C6_1 H6B_1 109.0 . . ? O3_1 C7_1 C6_1 127.6(7) . . ? O3_1 C7_1 C3_1 124.3(7) . . ? C6_1 C7_1 C3_1 108.1(7) . . ? N1_2 C8_1 C9_1 112.4(5) . . ? N1_2 C8_1 C3_1 112.5(5) . . ? C9_1 C8_1 C3_1 112.6(5) . . ? N1_2 C8_1 H8_1 106.2 . . ? C9_1 C8_1 H8_1 106.2 . . ? C3_1 C8_1 H8_1 106.2 . . ? C10_1 C9_1 C11_1 119.3(6) . . ? C10_1 C9_1 C8_1 119.4(6) . . ? C11_1 C9_1 C8_1 121.2(6) . . ? C9_1 C10_1 C14_1 122.2(6) . . ? C9_1 C10_1 H10_1 118.9 . . ? C14_1 C10_1 H10_1 118.9 . . ? C12_1 C11_1 C9_1 120.7(7) . . ? C12_1 C11_1 H11_1 119.7 . . ? C9_1 C11_1 H11_1 119.7 . . ? C11_1 C12_1 C13_1 120.8(6) . . ? C11_1 C12_1 H12_1 119.6 . . ? C13_1 C12_1 H12_1 119.6 . . ? C12_1 C13_1 C14_1 119.6(6) . . ? C12_1 C13_1 C18_1 122.1(7) . . ? C14_1 C13_1 C18_1 118.3(7) . . ? C15_1 C14_1 C13_1 119.3(7) . . ? C15_1 C14_1 C10_1 123.2(7) . . ? C13_1 C14_1 C10_1 117.4(6) . . ? C16_1 C15_1 C14_1 121.4(7) . . ? C16_1 C15_1 H15_1 119.3 . . ? C14_1 C15_1 H15_1 119.3 . . ? C15_1 C16_1 C17_1 119.9(8) . . ? C15_1 C16_1 H16_1 120.1 . . ? C17_1 C16_1 H16_1 120.1 . . ? C18_1 C17_1 C16_1 120.2(7) . . ? C18_1 C17_1 H17_1 119.9 . . ? C16_1 C17_1 H17_1 119.9 . . ? C17_1 C18_1 C13_1 120.9(7) . . ? C17_1 C18_1 H18_1 119.5 . . ? C13_1 C18_1 H18_1 119.5 . . ? O4_1 C19_1 O5_1 125.8(7) . . ? O4_1 C19_1 N1_2 125.4(7) . . ? O5_1 C19_1 N1_2 108.8(6) . . ? C21_1 C20_1 O5_1 111.0(8) . . ? C21_1 C20_1 C22_1 111.2(8) . . ? O5_1 C20_1 C22_1 103.5(6) . . ? C21_1 C20_1 C23_1 114.7(10) . . ? O5_1 C20_1 C23_1 105.3(7) . . ? C22_1 C20_1 C23_1 110.4(7) . . ? C20_1 C21_1 H21A_1 109.5 . . ? C20_1 C21_1 H21B_1 109.5 . . ? H21A_1 C21_1 H21B_1 109.5 . . ? C20_1 C21_1 H21C_1 109.5 . . ? H21A_1 C21_1 H21C_1 109.5 . . ? H21B_1 C21_1 H21C_1 109.5 . . ? C20_1 C22_1 H22A_1 109.5 . . ? C20_1 C22_1 H22B_1 109.5 . . ? H22A_1 C22_1 H22B_1 109.5 . . ? C20_1 C22_1 H22C_1 109.5 . . ? H22A_1 C22_1 H22C_1 109.5 . . ? H22B_1 C22_1 H22C_1 109.5 . . ? C20_1 C23_1 H23A_1 109.5 . . ? C20_1 C23_1 H23B_1 109.5 . . ? H23A_1 C23_1 H23B_1 109.5 . . ? C20_1 C23_1 H23C_1 109.5 . . ? H23A_1 C23_1 H23C_1 109.5 . . ? H23B_1 C23_1 H23C_1 109.5 . . ? C19_1 N1_2 C8_1 121.8(6) . . ? C19_1 N1_2 H1_2 119.1 . . ? C8_1 N1_2 H1_2 119.1 . . ? C2_2 O1_2 C1_2 109.8(8) . . ? C19_2 O5_2 C20_2 121.4(6) . . ? O1_2 C1_2 H1A_2 109.5 . . ? O1_2 C1_2 H1B_2 109.5 . . ? H1A_2 C1_2 H1B_2 109.5 . . ? O1_2 C1_2 H1C_2 109.5 . . ? H1A_2 C1_2 H1C_2 109.5 . . ? H1B_2 C1_2 H1C_2 109.5 . . ? O2_2 C2_2 O1_2 123.3(9) . . ? O2_2 C2_2 C3_2 124.7(10) . . ? O1_2 C2_2 C3_2 111.9(9) . . ? C2_2 C3_2 C7_2 110.0(6) . . ? C2_2 C3_2 C4_2 108.8(7) . . ? C7_2 C3_2 C4_2 103.4(6) . . ? C2_2 C3_2 C8_2 112.1(6) . . ? C7_2 C3_2 C8_2 111.1(6) . . ? C4_2 C3_2 C8_2 111.1(6) . . ? C5_2 C4_2 C3_2 105.6(7) . . ? C5_2 C4_2 H4A_2 110.6 . . ? C3_2 C4_2 H4A_2 110.6 . . ? C5_2 C4_2 H4B_2 110.6 . . ? C3_2 C4_2 H4B_2 110.6 . . ? H4A_2 C4_2 H4B_2 108.8 . . ? C4_2 C5_2 C6_2 108.4(8) . . ? C4_2 C5_2 H5A_2 110.0 . . ? C6_2 C5_2 H5A_2 110.0 . . ? C4_2 C5_2 H5B_2 110.0 . . ? C6_2 C5_2 H5B_2 110.0 . . ? H5A_2 C5_2 H5B_2 108.4 . . ? C7_2 C6_2 C5_2 104.0(7) . . ? C7_2 C6_2 H6A_2 111.0 . . ? C5_2 C6_2 H6A_2 111.0 . . ? C7_2 C6_2 H6B_2 111.0 . . ? C5_2 C6_2 H6B_2 111.0 . . ? H6A_2 C6_2 H6B_2 109.0 . . ? O3_2 C7_2 C6_2 124.0(7) . . ? O3_2 C7_2 C3_2 126.9(7) . . ? C6_2 C7_2 C3_2 109.1(7) . . ? N1_1 C8_2 C9_2 110.3(6) . . ? N1_1 C8_2 C3_2 113.7(6) . . ? C9_2 C8_2 C3_2 111.7(6) . . ? N1_1 C8_2 H8_2 106.9 . . ? C9_2 C8_2 H8_2 106.9 . . ? C3_2 C8_2 H8_2 106.9 . . ? C10_2 C9_2 C11_2 117.0(6) . . ? C10_2 C9_2 C8_2 121.6(6) . . ? C11_2 C9_2 C8_2 121.5(6) . . ? C9_2 C10_2 C14_2 122.6(6) . . ? C9_2 C10_2 H10_2 118.7 . . ? C14_2 C10_2 H10_2 118.7 . . ? C12_2 C11_2 C9_2 122.6(7) . . ? C12_2 C11_2 H11_2 118.7 . . ? C9_2 C11_2 H11_2 118.7 . . ? C11_2 C12_2 C13_2 120.7(6) . . ? C11_2 C12_2 H12_2 119.7 . . ? C13_2 C12_2 H12_2 119.7 . . ? C12_2 C13_2 C14_2 118.9(6) . . ? C12_2 C13_2 C18_2 122.4(7) . . ? C14_2 C13_2 C18_2 118.7(6) . . ? C10_2 C14_2 C15_2 124.4(7) . . ? C10_2 C14_2 C13_2 118.2(6) . . ? C15_2 C14_2 C13_2 117.4(6) . . ? C16_2 C15_2 C14_2 122.7(7) . . ? C16_2 C15_2 H15_2 118.7 . . ? C14_2 C15_2 H15_2 118.7 . . ? C17_2 C16_2 C15_2 119.0(7) . . ? C17_2 C16_2 H16_2 120.5 . . ? C15_2 C16_2 H16_2 120.5 . . ? C18_2 C17_2 C16_2 121.6(7) . . ? C18_2 C17_2 H17_2 119.2 . . ? C16_2 C17_2 H17_2 119.2 . . ? C17_2 C18_2 C13_2 120.5(7) . . ? C17_2 C18_2 H18_2 119.7 . . ? C13_2 C18_2 H18_2 119.7 . . ? O4_2 C19_2 N1_1 125.4(8) . . ? O4_2 C19_2 O5_2 124.5(8) . . ? N1_1 C19_2 O5_2 110.1(7) . . ? O5_2 C20_2 C23_2 110.9(6) . . ? O5_2 C20_2 C21_2 111.2(6) . . ? C23_2 C20_2 C21_2 111.9(7) . . ? O5_2 C20_2 C22_2 102.4(6) . . ? C23_2 C20_2 C22_2 111.2(7) . . ? C21_2 C20_2 C22_2 108.9(6) . . ? C20_2 C21_2 H21A_2 109.5 . . ? C20_2 C21_2 H21B_2 109.5 . . ? H21A_2 C21_2 H21B_2 109.5 . . ? C20_2 C21_2 H21C_2 109.5 . . ? H21A_2 C21_2 H21C_2 109.5 . . ? H21B_2 C21_2 H21C_2 109.5 . . ? C20_2 C22_2 H22A_2 109.5 . . ? C20_2 C22_2 H22B_2 109.5 . . ? H22A_2 C22_2 H22B_2 109.5 . . ? C20_2 C22_2 H22C_2 109.5 . . ? H22A_2 C22_2 H22C_2 109.5 . . ? H22B_2 C22_2 H22C_2 109.5 . . ? C20_2 C23_2 H23A_2 109.5 . . ? C20_2 C23_2 H23B_2 109.5 . . ? H23A_2 C23_2 H23B_2 109.5 . . ? C20_2 C23_2 H23C_2 109.5 . . ? H23A_2 C23_2 H23C_2 109.5 . . ? H23B_2 C23_2 H23C_2 109.5 . . ? 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 C1_1 O1_1 C2_1 O2_1 -0.2(10) . . . . ? C1_1 O1_1 C2_1 C3_1 177.8(6) . . . . ? O2_1 C2_1 C3_1 C4_1 -136.6(8) . . . . ? O1_1 C2_1 C3_1 C4_1 45.6(7) . . . . ? O2_1 C2_1 C3_1 C7_1 110.0(8) . . . . ? O1_1 C2_1 C3_1 C7_1 -67.9(7) . . . . ? O2_1 C2_1 C3_1 C8_1 -8.4(11) . . . . ? O1_1 C2_1 C3_1 C8_1 173.7(5) . . . . ? C2_1 C3_1 C4_1 C5_1 -100.4(7) . . . . ? C7_1 C3_1 C4_1 C5_1 15.3(7) . . . . ? C8_1 C3_1 C4_1 C5_1 130.6(6) . . . . ? C3_1 C4_1 C5_1 C6_1 -32.5(8) . . . . ? C4_1 C5_1 C6_1 C7_1 37.2(7) . . . . ? C5_1 C6_1 C7_1 O3_1 150.4(8) . . . . ? C5_1 C6_1 C7_1 C3_1 -28.6(7) . . . . ? C2_1 C3_1 C7_1 O3_1 -49.9(9) . . . . ? C4_1 C3_1 C7_1 O3_1 -170.3(7) . . . . ? C8_1 C3_1 C7_1 O3_1 71.9(8) . . . . ? C2_1 C3_1 C7_1 C6_1 129.1(6) . . . . ? C4_1 C3_1 C7_1 C6_1 8.7(7) . . . . ? C8_1 C3_1 C7_1 C6_1 -109.1(6) . . . . ? C2_1 C3_1 C8_1 N1_2 49.0(8) . . . . ? C4_1 C3_1 C8_1 N1_2 178.4(5) . . . . ? C7_1 C3_1 C8_1 N1_2 -69.0(7) . . . . ? C2_1 C3_1 C8_1 C9_1 -79.4(7) . . . . ? C4_1 C3_1 C8_1 C9_1 50.1(7) . . . . ? C7_1 C3_1 C8_1 C9_1 162.6(6) . . . . ? N1_2 C8_1 C9_1 C10_1 125.8(6) . . . . ? C3_1 C8_1 C9_1 C10_1 -105.8(7) . . . . ? N1_2 C8_1 C9_1 C11_1 -55.4(8) . . . . ? C3_1 C8_1 C9_1 C11_1 73.0(8) . . . . ? C11_1 C9_1 C10_1 C14_1 -1.1(10) . . . . ? C8_1 C9_1 C10_1 C14_1 177.7(6) . . . . ? C10_1 C9_1 C11_1 C12_1 1.2(10) . . . . ? C8_1 C9_1 C11_1 C12_1 -177.6(6) . . . . ? C9_1 C11_1 C12_1 C13_1 -0.8(10) . . . . ? C11_1 C12_1 C13_1 C14_1 0.3(10) . . . . ? C11_1 C12_1 C13_1 C18_1 -179.4(6) . . . . ? C12_1 C13_1 C14_1 C15_1 179.5(6) . . . . ? C18_1 C13_1 C14_1 C15_1 -0.8(9) . . . . ? C12_1 C13_1 C14_1 C10_1 -0.2(9) . . . . ? C18_1 C13_1 C14_1 C10_1 179.5(6) . . . . ? C9_1 C10_1 C14_1 C15_1 -179.1(6) . . . . ? C9_1 C10_1 C14_1 C13_1 0.6(9) . . . . ? C13_1 C14_1 C15_1 C16_1 -0.4(10) . . . . ? C10_1 C14_1 C15_1 C16_1 179.2(7) . . . . ? C14_1 C15_1 C16_1 C17_1 0.4(11) . . . . ? C15_1 C16_1 C17_1 C18_1 1.0(12) . . . . ? C16_1 C17_1 C18_1 C13_1 -2.3(11) . . . . ? C12_1 C13_1 C18_1 C17_1 -178.1(7) . . . . ? C14_1 C13_1 C18_1 C17_1 2.2(10) . . . . ? C20_1 O5_1 C19_1 O4_1 7.7(10) . . . . ? C20_1 O5_1 C19_1 N1_2 -171.8(6) . . . . ? C19_1 O5_1 C20_1 C21_1 -61.9(10) . . . . ? C19_1 O5_1 C20_1 C22_1 178.7(6) . . . . ? C19_1 O5_1 C20_1 C23_1 62.8(8) . . . . ? O4_1 C19_1 N1_2 C8_1 5.3(10) . . . . ? O5_1 C19_1 N1_2 C8_1 -175.2(5) . . . . ? C9_1 C8_1 N1_2 C19_1 -116.9(7) . . . . ? C3_1 C8_1 N1_2 C19_1 114.6(7) . . . . ? C1_2 O1_2 C2_2 O2_2 -3.8(10) . . . . ? C1_2 O1_2 C2_2 C3_2 178.3(6) . . . . ? O2_2 C2_2 C3_2 C7_2 -116.7(9) . . . . ? O1_2 C2_2 C3_2 C7_2 61.2(8) . . . . ? O2_2 C2_2 C3_2 C4_2 -4.1(10) . . . . ? O1_2 C2_2 C3_2 C4_2 173.8(6) . . . . ? O2_2 C2_2 C3_2 C8_2 119.1(9) . . . . ? O1_2 C2_2 C3_2 C8_2 -63.0(8) . . . . ? C2_2 C3_2 C4_2 C5_2 -138.8(7) . . . . ? C7_2 C3_2 C4_2 C5_2 -21.9(9) . . . . ? C8_2 C3_2 C4_2 C5_2 97.3(8) . . . . ? C3_2 C4_2 C5_2 C6_2 31.8(10) . . . . ? C4_2 C5_2 C6_2 C7_2 -28.3(10) . . . . ? C5_2 C6_2 C7_2 O3_2 -165.2(9) . . . . ? C5_2 C6_2 C7_2 C3_2 13.4(9) . . . . ? C2_2 C3_2 C7_2 O3_2 -60.5(11) . . . . ? C4_2 C3_2 C7_2 O3_2 -176.6(8) . . . . ? C8_2 C3_2 C7_2 O3_2 64.2(10) . . . . ? C2_2 C3_2 C7_2 C6_2 120.8(8) . . . . ? C4_2 C3_2 C7_2 C6_2 4.8(8) . . . . ? C8_2 C3_2 C7_2 C6_2 -114.4(7) . . . . ? C19_2 N1_1 C8_2 C9_2 -95.2(7) . . . . ? C19_2 N1_1 C8_2 C3_2 138.4(7) . . . . ? C2_2 C3_2 C8_2 N1_1 75.5(8) . . . . ? C7_2 C3_2 C8_2 N1_1 -48.0(8) . . . . ? C4_2 C3_2 C8_2 N1_1 -162.5(6) . . . . ? C2_2 C3_2 C8_2 C9_2 -50.1(9) . . . . ? C7_2 C3_2 C8_2 C9_2 -173.7(6) . . . . ? C4_2 C3_2 C8_2 C9_2 71.8(7) . . . . ? N1_1 C8_2 C9_2 C10_2 137.3(6) . . . . ? C3_2 C8_2 C9_2 C10_2 -95.2(7) . . . . ? N1_1 C8_2 C9_2 C11_2 -42.6(9) . . . . ? C3_2 C8_2 C9_2 C11_2 84.9(8) . . . . ? C11_2 C9_2 C10_2 C14_2 0.0(10) . . . . ? C8_2 C9_2 C10_2 C14_2 -179.9(7) . . . . ? C10_2 C9_2 C11_2 C12_2 0.5(10) . . . . ? C8_2 C9_2 C11_2 C12_2 -179.6(7) . . . . ? C9_2 C11_2 C12_2 C13_2 0.3(11) . . . . ? C11_2 C12_2 C13_2 C14_2 -1.4(11) . . . . ? C11_2 C12_2 C13_2 C18_2 178.5(7) . . . . ? C9_2 C10_2 C14_2 C15_2 -179.6(7) . . . . ? C9_2 C10_2 C14_2 C13_2 -1.1(10) . . . . ? C12_2 C13_2 C14_2 C10_2 1.8(10) . . . . ? C18_2 C13_2 C14_2 C10_2 -178.1(6) . . . . ? C12_2 C13_2 C14_2 C15_2 -179.6(6) . . . . ? C18_2 C13_2 C14_2 C15_2 0.5(10) . . . . ? C10_2 C14_2 C15_2 C16_2 177.7(8) . . . . ? C13_2 C14_2 C15_2 C16_2 -0.8(11) . . . . ? C14_2 C15_2 C16_2 C17_2 1.6(13) . . . . ? C15_2 C16_2 C17_2 C18_2 -2.2(13) . . . . ? C16_2 C17_2 C18_2 C13_2 2.0(12) . . . . ? C12_2 C13_2 C18_2 C17_2 179.0(7) . . . . ? C14_2 C13_2 C18_2 C17_2 -1.1(11) . . . . ? C8_2 N1_1 C19_2 O4_2 -4.4(11) . . . . ? C8_2 N1_1 C19_2 O5_2 177.0(6) . . . . ? C20_2 O5_2 C19_2 O4_2 17.0(11) . . . . ? C20_2 O5_2 C19_2 N1_1 -164.4(6) . . . . ? C19_2 O5_2 C20_2 C23_2 54.7(9) . . . . ? C19_2 O5_2 C20_2 C21_2 -70.4(8) . . . . ? C19_2 O5_2 C20_2 C22_2 173.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 22.46 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.308 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.079