# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Nazario Martin' _publ_contact_author_address ; Quimica Organica Universidad Complutense Madrid Madrid 28040 SPAIN ; _publ_contact_author_email NAZMAR@QUIM.UCM.ES _publ_section_title ; Synthesis and structural study of new lipophilic 1,4-dihydropyridines ; loop_ _publ_author_name 'Nazario Martin' 'Amaury Alvarez' 'Norbert M. Blanton' 'M.de Armas' 'Ramon Liz' ; R.Martinez-Alvarez ; 'Dolores Molero' 'Hector Novoa' 'Oswald M. Peeters' 'Oney Ramirez' 'Carlos Seoane' ; M.Suarez ; data_dhp5_2 _database_code_depnum_ccdc_archive 'CCDC 284120' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Decyl-5-octyl 2,6-dimethyl-4-(3'-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylate ; _chemical_name_common ;3-Decyl-5-octyl 2,6-dimethyl-4-(3'-pyridyl)-1,4-dihydropyridine- 3,5-dicarboxylate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H50 N2 O4' _chemical_formula_weight 526.74 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 Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.8754(7) _cell_length_b 16.1015(12) _cell_length_c 8.7774(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.021(7) _cell_angle_gamma 90.00 _cell_volume 3233.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 9.02 _cell_measurement_theta_max 24.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.553 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7434 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.1061 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 69.05 _reflns_number_total 5718 _reflns_number_gt 1522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_cell_refinement 'XSCANS (Siemens, 1996)' _computing_data_reduction 'XSCANS (Siemens, 1996)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Bergerhoff, 1996)' _computing_publication_material 'PARST (Nardelli, 1983)' _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^)+(0.1440P)^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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00027(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5718 _refine_ls_number_parameters 364 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2475 _refine_ls_R_factor_gt 0.0856 _refine_ls_wR_factor_ref 0.3405 _refine_ls_wR_factor_gt 0.2182 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.002 _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 0.1129(2) 0.0736(3) -0.0844(5) 0.0772(14) Uani 1 1 d . . . H1 H 0.0936 0.0922 -0.1612 0.096 Uiso 1 1 calc R . . C2 C 0.1604(3) 0.1189(4) -0.0315(6) 0.0722(17) Uani 1 1 d . . . C21 C 0.1823(3) 0.1824(4) -0.1426(6) 0.090(2) Uani 1 1 d . . . H21A H 0.1848 0.2355 -0.0933 0.134 Uiso 1 1 calc R . . H21B H 0.1560 0.1859 -0.2274 0.134 Uiso 1 1 calc R . . H21C H 0.2204 0.1665 -0.1782 0.134 Uiso 1 1 calc R . . C3 C 0.1813(3) 0.1033(3) 0.1072(6) 0.0648(15) Uani 1 1 d . . . C7 C 0.2353(3) 0.1408(4) 0.1639(6) 0.0711(16) Uani 1 1 d . . . O8 O 0.2660(2) 0.1896(3) 0.0946(5) 0.1044(16) Uani 1 1 d . . . O33 O 0.24905(17) 0.1162(2) 0.3044(4) 0.0761(12) Uani 1 1 d . . . C34 C 0.3029(3) 0.1473(4) 0.3695(6) 0.0825(19) Uani 1 1 d . . . H34A H 0.3019 0.2075 0.3738 0.103 Uiso 1 1 calc R . . H34B H 0.3358 0.1310 0.3063 0.103 Uiso 1 1 calc R . . C35 C 0.3101(3) 0.1129(4) 0.5254(7) 0.089(2) Uani 1 1 d . . . H35A H 0.3118 0.0528 0.5188 0.111 Uiso 1 1 calc R . . H35B H 0.2760 0.1273 0.5854 0.111 Uiso 1 1 calc R . . C36 C 0.3635(3) 0.1433(4) 0.6059(7) 0.093(2) Uani 1 1 d . . . H36A H 0.3973 0.1289 0.5448 0.116 Uiso 1 1 calc R . . H36B H 0.3616 0.2034 0.6109 0.116 Uiso 1 1 calc R . . C37 C 0.3729(3) 0.1111(5) 0.7626(7) 0.101(2) Uani 1 1 d . . . H37A H 0.3768 0.0512 0.7571 0.126 Uiso 1 1 calc R . . H37B H 0.3383 0.1230 0.8225 0.126 Uiso 1 1 calc R . . C38 C 0.4254(3) 0.1455(5) 0.8458(8) 0.113(3) Uani 1 1 d . . . H38A H 0.4599 0.1350 0.7844 0.142 Uiso 1 1 calc R . . H38B H 0.4209 0.2053 0.8534 0.142 Uiso 1 1 calc R . . C39 C 0.4362(4) 0.1122(6) 1.0014(8) 0.130(3) Uani 1 1 d . . . H39A H 0.4407 0.0524 0.9941 0.162 Uiso 1 1 calc R . . H39B H 0.4019 0.1230 1.0633 0.162 Uiso 1 1 calc R . . C310 C 0.4884(4) 0.1465(7) 1.0818(9) 0.163(4) Uani 1 1 d . B . H31A H 0.4839 0.2063 1.0897 0.204 Uiso 1 1 calc R . . H31B H 0.5227 0.1359 1.0198 0.204 Uiso 1 1 calc R . . C311 C 0.4994(5) 0.1118(8) 1.2407(11) 0.198(5) Uani 1 1 d . . . H31C H 0.4655 0.1207 1.3029 0.248 Uiso 1 1 calc R A 1 H31D H 0.5072 0.0533 1.2338 0.248 Uiso 1 1 calc R A 1 H31J H 0.5324 0.1394 1.2854 0.248 Uiso 0.50 1 calc R C 2 C312 C 0.5497(10) 0.1469(19) 1.320(2) 0.210(12) Uani 0.50 1 d P B 1 H31E H 0.5424 0.2057 1.3350 0.262 Uiso 0.50 1 calc PR B 1 H31F H 0.5833 0.1422 1.2530 0.262 Uiso 0.50 1 calc PR B 1 C313 C 0.566(3) 0.108(4) 1.477(4) 0.49(5) Uani 0.50 1 d P B 1 H31G H 0.6063 0.1214 1.5001 0.737 Uiso 0.50 1 calc PR B 1 H31H H 0.5616 0.0491 1.4725 0.737 Uiso 0.50 1 calc PR B 1 H31I H 0.5414 0.1307 1.5545 0.737 Uiso 0.50 1 calc PR B 1 C4 C 0.1498(2) 0.0422(3) 0.2147(6) 0.0644(15) Uani 1 1 d . . . H4 H 0.1795 0.0114 0.2721 0.080 Uiso 1 1 calc R . . C1' C 0.1105(2) 0.0884(3) 0.3291(5) 0.0620(15) Uani 1 1 d . . . C2' C 0.1156(3) 0.0738(4) 0.4822(6) 0.0834(19) Uani 1 1 d . . . H42 H 0.1445 0.0371 0.5142 0.104 Uiso 1 1 calc R . . N3' N 0.0817(3) 0.1085(4) 0.5891(5) 0.0935(17) Uani 1 1 d . . . C4' C 0.0411(3) 0.1617(4) 0.5419(7) 0.088(2) Uani 1 1 d . . . H44 H 0.0165 0.1857 0.6136 0.110 Uiso 1 1 calc R . . C5' C 0.0341(3) 0.1824(4) 0.3913(7) 0.0818(19) Uani 1 1 d . . . H45 H 0.0062 0.2213 0.3627 0.102 Uiso 1 1 calc R . . C6' C 0.0688(3) 0.1451(4) 0.2829(6) 0.0750(17) Uani 1 1 d . . . H46 H 0.0642 0.1579 0.1802 0.094 Uiso 1 1 calc R . . C5 C 0.1141(2) -0.0195(4) 0.1236(6) 0.0667(15) Uani 1 1 d . . . C9 C 0.1022(3) -0.1000(4) 0.1940(8) 0.0792(18) Uani 1 1 d . . . O10 O 0.0694(2) -0.1543(3) 0.1492(5) 0.1140(17) Uani 1 1 d . . . O53 O 0.1321(2) -0.1090(3) 0.3242(5) 0.0959(14) Uani 1 1 d . . . C54 C 0.1267(4) -0.1862(4) 0.4071(9) 0.113(3) Uani 1 1 d . . . H54A H 0.1290 -0.2329 0.3376 0.141 Uiso 1 1 calc R . . H54B H 0.0894 -0.1884 0.4594 0.141 Uiso 1 1 calc R . . C55 C 0.1747(6) -0.1894(7) 0.5173(14) 0.205(6) Uani 1 1 d . . . H55A H 0.1621 -0.2304 0.5912 0.256 Uiso 1 1 calc R . . H55B H 0.2064 -0.2155 0.4615 0.256 Uiso 1 1 calc R . . C56 C 0.2001(6) -0.1337(7) 0.5978(14) 0.180(5) Uani 1 1 d . . . H56A H 0.1691 -0.1072 0.6552 0.225 Uiso 1 1 calc R . . H56B H 0.2136 -0.0925 0.5252 0.225 Uiso 1 1 calc R . . C57 C 0.2496(6) -0.1436(7) 0.7091(15) 0.199(5) Uani 1 1 d . . . H57A H 0.2478 -0.2001 0.7476 0.248 Uiso 1 1 calc R . . H57B H 0.2856 -0.1390 0.6517 0.248 Uiso 1 1 calc R . . C58 C 0.2546(7) -0.0928(9) 0.8315(16) 0.204(6) Uani 1 1 d . . . H58A H 0.2165 -0.0911 0.8798 0.255 Uiso 1 1 calc R . . H58B H 0.2620 -0.0375 0.7922 0.255 Uiso 1 1 calc R . . C59 C 0.2978(7) -0.1075(11) 0.9537(17) 0.230(7) Uani 1 1 d . . . H59A H 0.3012 -0.1675 0.9588 0.287 Uiso 1 1 calc R . . H59B H 0.3345 -0.0883 0.9107 0.287 Uiso 1 1 calc R . . C510 C 0.2999(9) -0.0854(12) 1.086(2) 0.277(9) Uani 1 1 d . D . H51A H 0.2621 -0.1008 1.1272 0.346 Uiso 1 1 calc R . . H51B H 0.2997 -0.0252 1.0808 0.346 Uiso 1 1 calc R . . C511 C 0.3417(8) -0.1047(12) 1.2100(18) 0.239(7) Uani 1 1 d D . . H51C H 0.3772 -0.0740 1.1945 0.299 Uiso 1 1 calc R C 2 H51D H 0.3249 -0.0896 1.3062 0.299 Uiso 1 1 calc R C 2 H51J H 0.3502 -0.1631 1.2095 0.299 Uiso 0.50 1 calc R C 2 C512 C 0.3785(19) -0.153(2) 1.317(6) 0.52(5) Uani 0.50 1 d PD D 2 H51E H 0.4007 -0.1938 1.2607 0.655 Uiso 0.50 1 calc PR D 2 H51F H 0.3538 -0.1815 1.3891 0.655 Uiso 0.50 1 calc PR D 2 C513 C 0.419(2) -0.097(3) 1.400(6) 0.84(15) Uani 0.50 1 d PD D 2 H51G H 0.4401 -0.1279 1.4760 1.253 Uiso 0.50 1 calc PR D 2 H51H H 0.3975 -0.0530 1.4485 1.253 Uiso 0.50 1 calc PR D 2 H51I H 0.4467 -0.0729 1.3296 1.253 Uiso 0.50 1 calc PR D 2 C6 C 0.0953(3) -0.0011(4) -0.0181(7) 0.0760(17) Uani 1 1 d . . . C61 C 0.0552(3) -0.0516(4) -0.1184(6) 0.094(2) Uani 1 1 d . . . H61A H 0.0537 -0.1077 -0.0816 0.141 Uiso 1 1 calc R . . H61B H 0.0698 -0.0513 -0.2209 0.141 Uiso 1 1 calc R . . H61C H 0.0167 -0.0280 -0.1164 0.141 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 0.083(4) 0.084(4) 0.065(3) 0.004(3) -0.006(3) 0.005(3) C2 0.075(4) 0.078(4) 0.063(4) -0.002(3) 0.004(3) 0.000(4) C21 0.107(5) 0.091(5) 0.070(4) 0.022(4) 0.010(4) -0.014(4) C3 0.075(4) 0.058(3) 0.061(3) -0.003(3) 0.002(3) -0.005(3) C7 0.083(5) 0.074(4) 0.056(4) -0.003(3) 0.002(3) 0.000(4) O8 0.103(4) 0.118(4) 0.092(3) 0.027(3) -0.003(3) -0.031(3) O33 0.077(3) 0.087(3) 0.065(2) 0.001(2) -0.010(2) -0.012(2) C34 0.080(5) 0.096(5) 0.071(4) -0.006(4) -0.012(3) -0.007(4) C35 0.083(5) 0.105(5) 0.079(4) -0.009(4) -0.009(4) -0.002(4) C36 0.084(5) 0.115(6) 0.079(4) -0.004(4) -0.012(4) 0.006(4) C37 0.098(5) 0.124(6) 0.079(4) -0.011(4) -0.013(4) 0.006(5) C38 0.104(6) 0.144(7) 0.092(5) -0.008(5) -0.028(4) 0.011(5) C39 0.124(7) 0.173(9) 0.093(5) -0.006(6) -0.021(5) 0.014(6) C310 0.144(8) 0.237(12) 0.109(6) -0.036(7) -0.048(6) 0.026(8) C311 0.183(11) 0.299(16) 0.112(7) -0.010(9) -0.044(7) 0.047(11) C312 0.16(2) 0.35(4) 0.119(15) 0.00(2) -0.038(14) 0.01(2) C313 0.54(8) 0.75(12) 0.18(3) 0.18(5) 0.20(4) 0.36(8) C4 0.076(4) 0.057(3) 0.060(3) 0.001(3) -0.003(3) -0.007(3) C1' 0.076(4) 0.064(4) 0.046(3) -0.008(3) 0.004(3) -0.005(3) C2' 0.102(5) 0.092(5) 0.056(4) -0.006(3) -0.009(3) 0.014(4) N3' 0.122(5) 0.099(4) 0.059(3) -0.011(3) 0.003(3) 0.018(4) C4' 0.106(6) 0.095(5) 0.063(4) -0.015(4) 0.009(4) 0.006(5) C5' 0.090(5) 0.084(5) 0.072(4) -0.010(4) 0.003(4) 0.009(4) C6' 0.089(5) 0.081(4) 0.055(3) -0.001(3) 0.002(3) 0.007(4) C5 0.080(4) 0.058(4) 0.062(3) -0.010(3) 0.000(3) -0.009(3) C9 0.095(5) 0.067(4) 0.075(4) -0.009(4) 0.019(4) -0.009(4) O10 0.137(4) 0.083(3) 0.122(4) -0.001(3) -0.005(3) -0.038(3) O53 0.126(4) 0.069(3) 0.093(3) 0.017(2) -0.004(3) -0.012(3) C54 0.136(7) 0.080(5) 0.123(6) 0.023(5) 0.013(6) -0.017(5) C55 0.270(16) 0.134(10) 0.209(12) 0.093(9) -0.076(11) -0.088(10) C56 0.204(12) 0.120(9) 0.216(12) 0.047(9) -0.082(10) -0.006(8) C57 0.258(15) 0.159(11) 0.179(12) 0.061(9) -0.067(11) -0.006(11) C58 0.213(14) 0.235(15) 0.164(12) 0.002(11) -0.002(11) -0.022(12) C59 0.264(18) 0.276(18) 0.149(11) -0.008(13) -0.062(13) -0.035(14) C510 0.31(2) 0.32(2) 0.202(16) -0.019(18) -0.050(17) -0.008(18) C511 0.270(18) 0.26(2) 0.188(14) 0.000(13) -0.053(12) 0.015(17) C512 0.51(10) 0.24(5) 0.82(14) 0.25(8) 0.26(10) 0.06(6) C513 1.2(3) 0.23(5) 1.0(2) -0.28(10) 0.8(2) -0.20(11) C6 0.085(5) 0.077(4) 0.066(4) -0.016(3) 0.000(3) -0.002(4) C61 0.106(5) 0.104(5) 0.072(4) -0.028(4) 0.003(4) -0.018(4) _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 C2 1.388(7) . ? N1 C6 1.395(7) . ? C2 C3 1.333(7) . ? C2 C21 1.500(7) . ? C3 C7 1.461(8) . ? C3 C4 1.543(7) . ? C7 O8 1.216(6) . ? C7 O33 1.333(6) . ? O33 C34 1.448(6) . ? C34 C35 1.486(8) . ? C35 C36 1.493(8) . ? C36 C37 1.485(8) . ? C37 C38 1.512(9) . ? C38 C39 1.488(9) . ? C39 C310 1.493(10) . ? C310 C311 1.523(12) . ? C311 C312 1.46(2) . ? C312 C313 1.56(4) . ? C4 C5 1.514(7) . ? C4 C1' 1.540(7) . ? C1' C2' 1.369(7) . ? C1' C6' 1.382(7) . ? C2' N3' 1.338(7) . ? N3' C4' 1.330(7) . ? C4' C5' 1.372(7) . ? C5' C6' 1.377(7) . ? C5 C6 1.350(7) . ? C5 C9 1.462(8) . ? C9 O10 1.216(7) . ? C9 O53 1.340(7) . ? O53 C54 1.446(7) . ? C54 C55 1.464(12) . ? C55 C56 1.282(12) . ? C56 C57 1.503(14) . ? C57 C58 1.355(14) . ? C58 C59 1.479(16) . ? C59 C510 1.215(15) . ? C510 C511 1.482(19) . ? C511 C512 1.476(19) . ? C512 C513 1.49(2) . ? C6 C61 1.509(7) . ? 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 C2 N1 C6 122.7(5) . . ? C3 C2 N1 119.2(5) . . ? C3 C2 C21 127.0(6) . . ? N1 C2 C21 113.8(5) . . ? C2 C3 C7 122.5(5) . . ? C2 C3 C4 120.7(5) . . ? C7 C3 C4 116.8(5) . . ? O8 C7 O33 121.2(6) . . ? O8 C7 C3 125.8(6) . . ? O33 C7 C3 113.0(6) . . ? C7 O33 C34 117.6(5) . . ? O33 C34 C35 109.1(5) . . ? C34 C35 C36 113.8(6) . . ? C37 C36 C35 116.2(6) . . ? C36 C37 C38 115.8(6) . . ? C39 C38 C37 116.3(7) . . ? C38 C39 C310 115.6(8) . . ? C39 C310 C311 115.4(10) . . ? C312 C311 C310 115.0(15) . . ? C311 C312 C313 117(3) . . ? C5 C4 C1' 110.3(4) . . ? C5 C4 C3 110.4(4) . . ? C1' C4 C3 111.3(4) . . ? C2' C1' C6' 117.4(5) . . ? C2' C1' C4 120.5(5) . . ? C6' C1' C4 122.1(5) . . ? N3' C2' C1' 124.6(6) . . ? C4' N3' C2' 117.0(5) . . ? N3' C4' C5' 122.5(6) . . ? C4' C5' C6' 119.6(6) . . ? C5' C6' C1' 118.9(5) . . ? C6 C5 C9 121.7(6) . . ? C6 C5 C4 121.0(5) . . ? C9 C5 C4 117.3(5) . . ? O10 C9 O53 120.9(6) . . ? O10 C9 C5 128.0(7) . . ? O53 C9 C5 111.1(6) . . ? C9 O53 C54 118.5(6) . . ? O53 C54 C55 107.3(6) . . ? C56 C55 C54 132.8(12) . . ? C55 C56 C57 128.7(12) . . ? C58 C57 C56 120.9(14) . . ? C57 C58 C59 122.3(15) . . ? C510 C59 C58 132.2(19) . . ? C59 C510 C511 132(2) . . ? C512 C511 C510 161(2) . . ? C511 C512 C513 110.7(19) . . ? C5 C6 N1 118.8(6) . . ? C5 C6 C61 127.8(6) . . ? N1 C6 C61 113.4(5) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 69.05 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.258 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.049