# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Roberto Martinez' _publ_contact_author_address ; Organica Instituto de Qu mica, UNAM Circuito Exterior, CU Coyoac\'an M xico, D.F. 04510 MEXICO ; _publ_contact_author_email ROBMAR@SERVIDOR.UNAM.MX loop_ _publ_author_name 'Roberto Martinez' 'Jose R. Camacho' 'Yazmin M. Osornio' 'M. Teresa Ramirez-Apan' ; P.E.Reyes-Gutierrez ; # Attachment 'Comp16.cif' data_293MAR05 _database_code_depnum_ccdc_archive 'CCDC 770152' #TrackingRef 'Comp16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Etil 2-(3-{[4-Ciclohexilmetil)-1-piperazinil]-carbonil}-fenil)-8,9- dimetoxi-3-metil-5,6-dihidropirrolo[2,1-a]-isoquinolin-1-carboxilato ; _chemical_name_common ; Etil 2-(3-((4-Ciclohexilmetil)-1-piperazinil)-carbonil)- fenil)-8,9-dimetoxi-3-metil-5,6-dihidropirrolo(2,1-a)-isoquinolin-1- carboxilato ; _chemical_melting_point ? _chemical_formula_moiety 'C36 H45 N3 O5' _chemical_formula_sum 'C36 H45 N3 O5' _chemical_formula_weight 599.75 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.400(1) _cell_length_b 11.217(1) _cell_length_c 27.800(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.122(1) _cell_angle_gamma 90.00 _cell_volume 3224.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4656 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 24.57 _exptl_crystal_description square-pyram _exptl_crystal_colour colorless _exptl_crystal_size_min 0.162 _exptl_crystal_size_mid 0.162 _exptl_crystal_size_max 0.428 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details '(Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Bruker Smart Apex CCD diffractometer' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 0.661 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 26547 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.36 _reflns_number_total 5912 _reflns_number_gt 3654 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23C (Bruker, 1999)' _computing_structure_solution 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0583P)^2^+1.0814P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5912 _refine_ls_number_parameters 465 _refine_ls_number_restraints 264 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.018 _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 0.5741(3) 1.0142(3) 0.17649(10) 0.1500(14) Uani 1 1 d . . . O2 O 0.64922(19) 0.8350(2) 0.17393(6) 0.0790(6) Uani 1 1 d . . . O3 O 0.2190(3) 1.4204(2) 0.06979(9) 0.1160(9) Uani 1 1 d . . . O4 O 0.4071(3) 1.3754(2) 0.13441(9) 0.1131(9) Uani 1 1 d . . . O5 O 1.04529(18) 0.74987(18) 0.06392(7) 0.0745(6) Uani 1 1 d . . . C1 C 0.5300(2) 0.8983(2) 0.10445(9) 0.0530(6) Uani 1 1 d . . . C2 C 0.5535(2) 0.7901(2) 0.07949(9) 0.0522(6) Uani 1 1 d . . . C3 C 0.4689(2) 0.7866(2) 0.03820(9) 0.0547(7) Uani 1 1 d . . . N4 N 0.39558(19) 0.88877(19) 0.03710(7) 0.0538(5) Uani 1 1 d . . . C5 C 0.2998(3) 0.9244(3) -0.00321(10) 0.0689(8) Uani 1 1 d . . . H5A H 0.2595 0.8541 -0.0186 0.083 Uiso 1 1 calc R . . H5B H 0.3422 0.9680 -0.0272 0.083 Uiso 1 1 calc R . . C6 C 0.1997(3) 1.0009(3) 0.01566(11) 0.0755(9) Uani 1 1 d . . . H6A H 0.1472 0.9531 0.0351 0.091 Uiso 1 1 calc R . . H6B H 0.1435 1.0336 -0.0112 0.091 Uiso 1 1 calc R . . C6A C 0.2611(3) 1.1006(3) 0.04575(10) 0.0641(7) Uani 1 1 d . . . C7 C 0.2111(3) 1.2155(3) 0.04233(11) 0.0800(9) Uani 1 1 d . . . H7 H 0.1416 1.2318 0.0194 0.096 Uiso 1 1 calc R . . C8 C 0.2615(4) 1.3054(3) 0.07184(11) 0.0802(9) Uani 1 1 d . . . C9 C 0.3645(3) 1.2808(3) 0.10613(10) 0.0757(9) Uani 1 1 d . . . C10 C 0.4189(3) 1.1696(3) 0.10882(10) 0.0674(8) Uani 1 1 d . . . H10 H 0.4900 1.1551 0.1313 0.081 Uiso 1 1 calc R . . C10A C 0.3695(3) 1.0767(2) 0.07818(9) 0.0566(7) Uani 1 1 d . . . C10B C 0.4313(2) 0.9594(2) 0.07646(9) 0.0528(6) Uani 1 1 d . . . C11 C 0.5859(3) 0.9259(3) 0.15380(11) 0.0680(8) Uani 1 1 d . . . C12 C 0.4509(3) 0.6964(3) -0.00119(10) 0.0714(8) Uani 1 1 d . . . H12A H 0.5189 0.6383 0.0033 0.107 Uiso 1 1 calc R . . H12B H 0.4533 0.7351 -0.0319 0.107 Uiso 1 1 calc R . . H12C H 0.3689 0.6576 -0.0004 0.107 Uiso 1 1 calc R . . C13 C 0.6557(2) 0.6991(2) 0.09059(9) 0.0550(7) Uani 1 1 d . . . C14 C 0.7857(2) 0.7310(2) 0.09267(9) 0.0527(6) Uani 1 1 d . . . H14 H 0.8072 0.8106 0.0887 0.063 Uiso 1 1 calc R . . C15 C 0.8840(2) 0.6473(2) 0.10056(9) 0.0523(6) Uani 1 1 d . . . C16 C 0.8514(3) 0.5285(2) 0.10520(10) 0.0630(7) Uani 1 1 d . . . H16 H 0.9160 0.4712 0.1103 0.076 Uiso 1 1 calc R . . C17 C 0.7236(3) 0.4951(3) 0.10232(11) 0.0723(8) Uani 1 1 d . . . H17 H 0.7023 0.4150 0.1049 0.087 Uiso 1 1 calc R . . C18 C 0.6265(3) 0.5794(3) 0.09556(10) 0.0683(8) Uani 1 1 d . . . H18 H 0.5406 0.5556 0.0943 0.082 Uiso 1 1 calc R . . C19 C 1.0207(2) 0.6885(2) 0.09825(10) 0.0542(7) Uani 1 1 d . . . N20 N 1.11184(19) 0.6535(2) 0.13325(8) 0.0584(6) Uani 1 1 d . A . C21 C 1.0914(3) 0.5924(3) 0.17799(10) 0.0650(8) Uani 1 1 d . . . H21A H 1.1286 0.5131 0.1779 0.078 Uiso 1 1 calc R . . H21B H 0.9994 0.5843 0.1803 0.078 Uiso 1 1 calc R . . C22 C 1.1529(3) 0.6609(3) 0.22087(10) 0.0709(8) Uani 1 1 d . A . H22A H 1.1108 0.7378 0.2223 0.085 Uiso 1 1 calc R . . H22B H 1.1410 0.6178 0.2503 0.085 Uiso 1 1 calc R . . N23 N 1.2899(2) 0.6787(2) 0.21789(9) 0.0726(7) Uani 1 1 d D . . C24 C 1.3075(3) 0.7436(3) 0.17357(12) 0.0780(9) Uani 1 1 d . A . H24A H 1.3992 0.7545 0.1713 0.094 Uiso 1 1 calc R . . H24B H 1.2682 0.8218 0.1748 0.094 Uiso 1 1 calc R . . C25 C 1.2486(3) 0.6789(3) 0.12978(11) 0.0721(8) Uani 1 1 d . . . H25A H 1.2568 0.7270 0.1013 0.087 Uiso 1 1 calc R A . H25B H 1.2947 0.6047 0.1264 0.087 Uiso 1 1 calc R . . C26 C 1.3690(13) 0.7417(10) 0.2557(3) 0.075(3) Uani 0.502(5) 1 d PDU A 1 H26A H 1.3250 0.8141 0.2638 0.090 Uiso 0.502(5) 1 calc PR A 1 H26B H 1.4501 0.7643 0.2440 0.090 Uiso 0.502(5) 1 calc PR A 1 C27 C 1.3962(9) 0.6664(7) 0.3004(3) 0.071(2) Uani 0.502(5) 1 d PDU A 1 H27 H 1.3132 0.6525 0.3132 0.085 Uiso 0.502(5) 1 calc PR A 1 C28 C 1.4791(11) 0.7390(9) 0.3380(4) 0.078(2) Uani 0.502(5) 1 d PDU A 1 H28A H 1.5530 0.7692 0.3233 0.093 Uiso 0.502(5) 1 calc PR A 1 H28B H 1.4290 0.8072 0.3467 0.093 Uiso 0.502(5) 1 calc PR A 1 C29 C 1.5278(8) 0.6736(6) 0.3837(2) 0.0833(17) Uani 0.502(5) 1 d PDU A 1 H29A H 1.4557 0.6550 0.4019 0.100 Uiso 0.502(5) 1 calc PR A 1 H29B H 1.5873 0.7244 0.4037 0.100 Uiso 0.502(5) 1 calc PR A 1 C30 C 1.5966(10) 0.5584(8) 0.3721(3) 0.083(2) Uani 0.502(5) 1 d PDU A 1 H30A H 1.6322 0.5177 0.4013 0.100 Uiso 0.502(5) 1 calc PR A 1 H30B H 1.6652 0.5734 0.3518 0.100 Uiso 0.502(5) 1 calc PR A 1 C31 C 1.4824(11) 0.4850(10) 0.3442(4) 0.085(2) Uani 0.502(5) 1 d PDU A 1 H31A H 1.4063 0.4876 0.3615 0.102 Uiso 0.502(5) 1 calc PR A 1 H31B H 1.5075 0.4024 0.3406 0.102 Uiso 0.502(5) 1 calc PR A 1 C32 C 1.4543(8) 0.5467(5) 0.2928(2) 0.0744(16) Uani 0.502(5) 1 d PDU A 1 H32A H 1.5339 0.5555 0.2779 0.089 Uiso 0.502(5) 1 calc PR A 1 H32B H 1.3948 0.4985 0.2717 0.089 Uiso 0.502(5) 1 calc PR A 1 C26B C 1.3372(12) 0.7400(10) 0.2659(4) 0.075(3) Uani 0.498(5) 1 d PDU A 2 H26C H 1.3693 0.8187 0.2591 0.090 Uiso 0.498(5) 1 calc PR A 2 H26D H 1.2645 0.7499 0.2847 0.090 Uiso 0.498(5) 1 calc PR A 2 C27B C 1.4412(8) 0.6725(7) 0.2953(4) 0.070(2) Uani 0.498(5) 1 d PDU A 2 H27B H 1.5038 0.6497 0.2730 0.084 Uiso 0.498(5) 1 calc PR A 2 C28B C 1.5153(11) 0.7460(10) 0.3346(4) 0.074(2) Uani 0.498(5) 1 d PDU A 2 H28C H 1.4552 0.7775 0.3558 0.088 Uiso 0.498(5) 1 calc PR A 2 H28D H 1.5551 0.8130 0.3199 0.088 Uiso 0.498(5) 1 calc PR A 2 C29B C 1.6200(8) 0.6754(6) 0.3648(3) 0.0814(18) Uani 0.498(5) 1 d PDU A 2 H29C H 1.6574 0.7241 0.3916 0.098 Uiso 0.498(5) 1 calc PR A 2 H29D H 1.6882 0.6548 0.3450 0.098 Uiso 0.498(5) 1 calc PR A 2 C30B C 1.5633(11) 0.5608(8) 0.3846(3) 0.084(2) Uani 0.498(5) 1 d PDU A 2 H30C H 1.4919 0.5795 0.4031 0.100 Uiso 0.498(5) 1 calc PR A 2 H30D H 1.6287 0.5179 0.4052 0.100 Uiso 0.498(5) 1 calc PR A 2 C31B C 1.5157(11) 0.4856(9) 0.3388(4) 0.083(2) Uani 0.498(5) 1 d PDU A 2 H31C H 1.4912 0.4058 0.3477 0.099 Uiso 0.498(5) 1 calc PR A 2 H31D H 1.5821 0.4802 0.3169 0.099 Uiso 0.498(5) 1 calc PR A 2 C32B C 1.3929(7) 0.5587(6) 0.3147(3) 0.0771(17) Uani 0.498(5) 1 d PDU A 2 H32C H 1.3470 0.5126 0.2888 0.093 Uiso 0.498(5) 1 calc PR A 2 H32D H 1.3340 0.5754 0.3387 0.093 Uiso 0.498(5) 1 calc PR A 2 C33 C 0.7085(3) 0.8432(4) 0.22283(11) 0.0939(11) Uani 1 1 d . . . H33A H 0.6443 0.8611 0.2446 0.113 Uiso 1 1 calc R . . H33B H 0.7736 0.9055 0.2257 0.113 Uiso 1 1 calc R . . C34 C 0.7687(4) 0.7248(4) 0.23446(13) 0.1244(16) Uani 1 1 d . . . H34A H 0.7050 0.6634 0.2280 0.187 Uiso 1 1 calc R . . H34B H 0.8020 0.7227 0.2680 0.187 Uiso 1 1 calc R . . H34C H 0.8381 0.7121 0.2148 0.187 Uiso 1 1 calc R . . C35 C 0.1453(4) 1.4575(4) 0.02945(14) 0.1270(16) Uani 1 1 d . . . H35A H 0.1888 1.4400 0.0015 0.190 Uiso 1 1 calc R . . H35B H 0.1314 1.5419 0.0313 0.190 Uiso 1 1 calc R . . H35C H 0.0636 1.4170 0.0269 0.190 Uiso 1 1 calc R . . C36 C 0.4835(4) 1.3575(4) 0.17532(14) 0.1229(15) Uani 1 1 d . . . H36A H 0.4513 1.2915 0.1925 0.184 Uiso 1 1 calc R . . H36B H 0.4845 1.4278 0.1951 0.184 Uiso 1 1 calc R . . H36C H 0.5696 1.3402 0.1680 0.184 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 0.244(4) 0.094(2) 0.0909(19) -0.0272(16) -0.079(2) 0.038(2) O2 0.0789(14) 0.1047(16) 0.0492(11) 0.0062(11) -0.0132(10) 0.0149(12) O3 0.186(3) 0.0759(16) 0.0830(17) -0.0068(13) -0.0005(17) 0.0481(17) O4 0.180(3) 0.0709(15) 0.0818(17) -0.0075(13) -0.0181(17) -0.0102(16) O5 0.0665(13) 0.0822(14) 0.0744(13) 0.0250(12) 0.0056(10) -0.0030(11) C1 0.0473(15) 0.0615(17) 0.0482(15) 0.0037(13) -0.0036(12) -0.0090(13) C2 0.0431(14) 0.0590(16) 0.0531(15) 0.0044(13) -0.0015(12) -0.0059(12) C3 0.0495(15) 0.0613(17) 0.0527(16) 0.0001(13) 0.0021(12) -0.0014(13) N4 0.0483(12) 0.0641(14) 0.0464(12) 0.0009(11) -0.0063(9) 0.0038(11) C5 0.0637(18) 0.082(2) 0.0564(17) -0.0040(15) -0.0150(14) 0.0102(16) C6 0.0629(19) 0.085(2) 0.075(2) -0.0003(17) -0.0110(15) 0.0163(16) C6A 0.0652(18) 0.0697(19) 0.0563(17) -0.0013(15) 0.0003(14) 0.0074(15) C7 0.088(2) 0.082(2) 0.068(2) 0.0014(18) -0.0025(17) 0.0258(19) C8 0.114(3) 0.065(2) 0.062(2) -0.0004(17) 0.0111(19) 0.0197(19) C9 0.113(3) 0.061(2) 0.0533(18) -0.0016(16) 0.0101(18) -0.0062(18) C10 0.080(2) 0.0645(19) 0.0561(17) 0.0044(15) 0.0004(15) -0.0030(16) C10A 0.0592(17) 0.0600(17) 0.0497(15) 0.0055(13) 0.0015(13) -0.0015(14) C10B 0.0501(15) 0.0589(16) 0.0482(15) 0.0037(13) 0.0003(12) -0.0087(13) C11 0.072(2) 0.068(2) 0.0601(19) 0.0007(17) -0.0128(15) -0.0028(16) C12 0.0699(19) 0.078(2) 0.0637(18) -0.0088(16) -0.0037(15) 0.0105(16) C13 0.0506(16) 0.0575(16) 0.0548(16) 0.0048(13) -0.0046(12) -0.0039(13) C14 0.0535(16) 0.0467(14) 0.0558(15) 0.0041(12) -0.0039(12) -0.0043(12) C15 0.0525(16) 0.0507(15) 0.0516(15) 0.0044(12) -0.0040(12) -0.0004(13) C16 0.0630(18) 0.0513(17) 0.0710(19) 0.0063(14) -0.0102(14) 0.0027(14) C17 0.071(2) 0.0530(17) 0.089(2) 0.0124(16) -0.0108(16) -0.0131(15) C18 0.0554(17) 0.0669(19) 0.080(2) 0.0141(16) -0.0065(15) -0.0130(15) C19 0.0526(16) 0.0484(15) 0.0604(17) 0.0014(13) 0.0012(13) 0.0015(13) N20 0.0466(13) 0.0661(14) 0.0613(14) 0.0092(12) -0.0009(11) 0.0001(11) C21 0.0552(17) 0.0659(18) 0.0716(19) 0.0116(16) -0.0045(14) -0.0051(14) C22 0.074(2) 0.0702(19) 0.0656(18) 0.0085(16) -0.0061(15) -0.0072(16) N23 0.0639(16) 0.0635(15) 0.0838(17) 0.0084(14) -0.0219(13) -0.0074(12) C24 0.0517(17) 0.077(2) 0.103(2) 0.012(2) -0.0052(16) -0.0067(15) C25 0.0471(17) 0.085(2) 0.084(2) 0.0083(18) 0.0043(15) 0.0036(15) C26 0.074(5) 0.062(3) 0.084(4) 0.008(3) -0.017(4) -0.012(4) C27 0.079(4) 0.057(3) 0.072(3) -0.004(2) -0.013(3) -0.001(3) C28 0.094(5) 0.056(3) 0.078(3) -0.010(3) -0.016(4) 0.005(3) C29 0.101(4) 0.075(3) 0.069(3) -0.009(3) -0.011(3) 0.001(3) C30 0.101(4) 0.069(3) 0.074(4) 0.004(3) -0.016(3) 0.007(3) C31 0.108(5) 0.060(3) 0.084(3) 0.005(3) -0.011(4) -0.002(3) C32 0.093(4) 0.059(3) 0.069(3) -0.008(2) -0.006(3) 0.003(3) C26B 0.069(5) 0.060(3) 0.090(4) -0.005(3) -0.017(4) -0.003(3) C27B 0.080(4) 0.057(3) 0.067(3) -0.001(2) -0.014(3) -0.004(3) C28B 0.086(5) 0.062(3) 0.068(3) -0.003(3) -0.014(3) -0.012(3) C29B 0.096(4) 0.073(3) 0.069(3) -0.004(3) -0.023(3) -0.010(3) C30B 0.100(5) 0.072(3) 0.074(4) 0.006(3) -0.012(3) 0.005(3) C31B 0.104(5) 0.058(3) 0.083(4) 0.007(3) -0.010(4) -0.005(3) C32B 0.086(4) 0.063(3) 0.078(4) -0.003(3) -0.007(3) -0.012(3) C33 0.077(2) 0.144(3) 0.0549(19) 0.019(2) -0.0171(16) -0.010(2) C34 0.098(3) 0.188(5) 0.083(3) 0.044(3) -0.010(2) 0.033(3) C35 0.177(4) 0.102(3) 0.099(3) 0.006(2) -0.002(3) 0.074(3) C36 0.173(4) 0.110(3) 0.081(3) -0.008(2) -0.010(3) -0.046(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.188(4) . ? O2 C11 1.307(3) . ? O2 C33 1.435(3) . ? O3 C35 1.355(4) . ? O3 C8 1.363(4) . ? O4 C36 1.331(4) . ? O4 C9 1.367(4) . ? O5 C19 1.226(3) . ? C1 C10B 1.400(3) . ? C1 C2 1.432(4) . ? C1 C11 1.465(4) . ? C2 C3 1.371(3) . ? C2 C13 1.481(3) . ? C3 N4 1.375(3) . ? C3 C12 1.488(4) . ? N4 C10B 1.370(3) . ? N4 C5 1.473(3) . ? C5 C6 1.487(4) . ? C6 C6A 1.498(4) . ? C6A C7 1.389(4) . ? C6A C10A 1.393(4) . ? C7 C8 1.368(4) . ? C8 C9 1.384(4) . ? C9 C10 1.369(4) . ? C10 C10A 1.408(4) . ? C10A C10B 1.467(4) . ? C13 C18 1.387(4) . ? C13 C14 1.395(3) . ? C14 C15 1.388(3) . ? C15 C16 1.385(4) . ? C15 C19 1.502(3) . ? C16 C17 1.375(4) . ? C17 C18 1.381(4) . ? C19 N20 1.343(3) . ? N20 C21 1.455(3) . ? N20 C25 1.464(3) . ? C21 C22 1.503(4) . ? C22 N23 1.449(4) . ? N23 C26 1.449(9) . ? N23 C24 1.459(4) . ? N23 C26B 1.534(9) . ? C24 C25 1.491(4) . ? C26 C27 1.504(11) . ? C27 C32 1.497(10) . ? C27 C28 1.518(9) . ? C28 C29 1.507(10) . ? C29 C30 1.529(10) . ? C30 C31 1.579(11) . ? C31 C32 1.586(11) . ? C26B C27B 1.492(11) . ? C27B C32B 1.493(9) . ? C27B C28B 1.513(9) . ? C28B C29B 1.524(9) . ? C29B C30B 1.539(10) . ? C30B C31B 1.562(11) . ? C31B C32B 1.603(10) . ? C33 C34 1.489(5) . ? 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 C11 O2 C33 120.1(3) . . ? C35 O3 C8 118.5(3) . . ? C36 O4 C9 120.1(3) . . ? C10B C1 C2 107.4(2) . . ? C10B C1 C11 127.7(3) . . ? C2 C1 C11 124.2(2) . . ? C3 C2 C1 107.6(2) . . ? C3 C2 C13 122.5(2) . . ? C1 C2 C13 129.7(2) . . ? C2 C3 N4 107.5(2) . . ? C2 C3 C12 130.9(2) . . ? N4 C3 C12 121.6(2) . . ? C10B N4 C3 111.2(2) . . ? C10B N4 C5 123.7(2) . . ? C3 N4 C5 124.9(2) . . ? N4 C5 C6 109.3(2) . . ? C5 C6 C6A 110.8(2) . . ? C7 C6A C10A 119.6(3) . . ? C7 C6A C6 121.4(3) . . ? C10A C6A C6 119.0(3) . . ? C8 C7 C6A 121.8(3) . . ? O3 C8 C7 124.8(3) . . ? O3 C8 C9 116.2(3) . . ? C7 C8 C9 119.0(3) . . ? O4 C9 C10 124.7(3) . . ? O4 C9 C8 114.9(3) . . ? C10 C9 C8 120.3(3) . . ? C9 C10 C10A 121.3(3) . . ? C6A C10A C10 117.9(3) . . ? C6A C10A C10B 118.6(2) . . ? C10 C10A C10B 123.4(2) . . ? N4 C10B C1 106.3(2) . . ? N4 C10B C10A 117.5(2) . . ? C1 C10B C10A 136.0(2) . . ? O1 C11 O2 119.9(3) . . ? O1 C11 C1 128.4(3) . . ? O2 C11 C1 111.6(3) . . ? C18 C13 C14 117.7(2) . . ? C18 C13 C2 121.9(2) . . ? C14 C13 C2 120.2(2) . . ? C15 C14 C13 121.8(2) . . ? C16 C15 C14 118.8(2) . . ? C16 C15 C19 122.9(2) . . ? C14 C15 C19 118.0(2) . . ? C17 C16 C15 120.2(3) . . ? C16 C17 C18 120.6(3) . . ? C17 C18 C13 120.8(3) . . ? O5 C19 N20 122.6(2) . . ? O5 C19 C15 118.9(2) . . ? N20 C19 C15 118.5(2) . . ? C19 N20 C21 126.9(2) . . ? C19 N20 C25 120.7(2) . . ? C21 N20 C25 112.3(2) . . ? N20 C21 C22 110.4(2) . . ? N23 C22 C21 111.3(2) . . ? C22 N23 C26 120.7(6) . . ? C22 N23 C24 109.2(2) . . ? C26 N23 C24 104.9(5) . . ? C22 N23 C26B 103.8(6) . . ? C24 N23 C26B 117.0(5) . . ? N23 C24 C25 111.7(2) . . ? N20 C25 C24 111.0(2) . . ? N23 C26 C27 111.6(8) . . ? C32 C27 C26 115.4(10) . . ? C32 C27 C28 111.8(7) . . ? C26 C27 C28 108.1(7) . . ? C29 C28 C27 115.8(7) . . ? C28 C29 C30 110.8(7) . . ? C29 C30 C31 101.6(9) . . ? C30 C31 C32 105.8(8) . . ? C27 C32 C31 107.6(8) . . ? C27B C26B N23 113.3(9) . . ? C26B C27B C32B 112.3(9) . . ? C26B C27B C28B 113.8(8) . . ? C32B C27B C28B 111.7(7) . . ? C27B C28B C29B 113.2(8) . . ? C28B C29B C30B 110.6(8) . . ? C29B C30B C31B 105.1(8) . . ? C30B C31B C32B 103.5(9) . . ? C27B C32B C31B 107.7(8) . . ? O2 C33 C34 106.1(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.230 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.032