# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Trabocchi, Andrea' _publ_contact_author_email andrea.trabocchi@unifi.it _publ_section_title ; Skeletal diversity by sequential one-pot and stepwise routes using morpholine ester scaffolds ; loop_ _publ_author_name A.Trabocchi I.Stefanini M.Morvillo L.Ciofi D.Cavalieri A.Guarna data_exp_259 _database_code_depnum_ccdc_archive 'CCDC 769053' #TrackingRef 'exp_259.cif' _audit_creation_date ; 'Thu Mar 04 16:55:25 2010' ; _audit_creation_method ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _chemical_name_systematic ; methyl-6-benzyl-2-methyl-5-oxohexahydro-5H-[1,3]oxazolo [3,2-a]pyrazine-3-carboxylate ; _chemical_name_common ; methyl-6-benzyl-2-methyl-5-oxohexahydro-5H-(1,3)oxazolo (3,2- a)pyrazine-3-carboxylate ; _chemical_formula_moiety 'C16 H20 N2 O4' _chemical_formula_sum 'C32 H40 N4 O8' _chemical_melting_point ? _exptl_crystal_description prismatic _exptl_crystal_colour white _diffrn_ambient_temperature 293(2) _chemical_formula_weight 608.68 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_H-M 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.757(1) _cell_length_b 18.607(1) _cell_length_c 10.809(1) _cell_angle_alpha 90.00 _cell_angle_beta 92.211(2) _cell_angle_gamma 90.00 _cell_volume 1559.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3465 _cell_measurement_theta_min 4.7310 _cell_measurement_theta_max 70.3639 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.773 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9184 _exptl_absorpt_correction_T_max 0.9400 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe X-Ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Onyx' _diffrn_measurement_method 'profile data from omega scan' _diffrn_detector_area_resol_mean 8.1241 _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 50 _diffrn_reflns_number 7877 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.73 _diffrn_reflns_theta_max 70.56 _reflns_number_total 4396 _reflns_number_gt 3175 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 1.00 49.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -4.8771 77.0000 90.0000 48 #__ type_ start__ end____ width___ exp.time_ 2 omega -92.00 -36.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -4.8771 179.0000 -120.0000 56 #__ type_ start__ end____ width___ exp.time_ 3 omega 34.00 93.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 4.8771 179.0000 -30.0000 59 #__ type_ start__ end____ width___ exp.time_ 4 omega -59.00 -13.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 15.0000 30.0000 46 #__ type_ start__ end____ width___ exp.time_ 5 omega -112.00 -18.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 77.0000 -60.0000 94 #__ type_ start__ end____ width___ exp.time_ 6 omega -96.00 -41.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 77.0000 0.0000 55 #__ type_ start__ end____ width___ exp.time_ 7 omega 89.00 165.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 96.6919 45.0000 -90.0000 76 #__ type_ start__ end____ width___ exp.time_ 8 omega 61.00 167.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 96.6919 15.0000 -150.0000 106 #__ type_ start__ end____ width___ exp.time_ 9 omega 113.00 140.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 96.6919 125.0000 90.0000 27 #__ type_ start__ end____ width___ exp.time_ 10 omega -77.00 25.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -4.8771 -77.0000 30.0000 102 #__ type_ start__ end____ width___ exp.time_ 11 omega -76.00 18.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -4.8771 -37.0000 120.0000 94 #__ type_ start__ end____ width___ exp.time_ 12 omega -167.00 -96.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 -15.0000 30.0000 71 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution Sir2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Ciftab _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^)+(0.0665P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(2) _refine_ls_number_reflns 4396 _refine_ls_number_parameters 405 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 N1A N 0.2448(4) -0.23799(14) -0.1443(2) 0.0508(7) Uani 1 1 d . . . N2A N 0.4122(4) -0.16139(15) 0.0454(3) 0.0559(7) Uani 1 1 d . . . O1A O -0.0131(3) -0.18707(14) -0.1108(2) 0.0660(7) Uani 1 1 d . . . O2A O 0.2852(5) -0.24759(19) -0.4045(3) 0.1070(12) Uani 1 1 d . . . O3A O 0.1157(3) -0.34423(13) -0.4051(2) 0.0687(7) Uani 1 1 d . . . O4A O 0.4275(3) -0.33065(14) -0.1273(3) 0.0706(7) Uani 1 1 d . . . C1A C 0.1663(5) -0.17216(18) -0.0976(3) 0.0550(9) Uani 1 1 d . . . H1A H 0.1961 -0.1310 -0.1490 0.066 Uiso 1 1 calc R . . C2A C 0.2252(5) -0.1595(2) 0.0345(3) 0.0624(10) Uani 1 1 d . . . H2A1 H 0.1840 -0.1131 0.0617 0.075 Uiso 1 1 calc R . . H2A2 H 0.1776 -0.1962 0.0869 0.075 Uiso 1 1 calc R . . C3A C 0.4841(5) -0.23100(18) 0.0095(3) 0.0541(8) Uani 1 1 d . . . H3A H 0.5993 -0.2215 -0.0209 0.065 Uiso 1 1 calc R . . C4A C 0.3836(4) -0.27084(19) -0.0932(3) 0.0507(8) Uani 1 1 d . . . C5A C 0.1228(4) -0.27545(18) -0.2262(3) 0.0503(8) Uani 1 1 d . . . H5A H 0.0923 -0.3217 -0.1897 0.060 Uiso 1 1 calc R . . C6A C -0.0337(4) -0.22473(19) -0.2270(3) 0.0556(9) Uani 1 1 d . . . H6A H -0.0253 -0.1904 -0.2952 0.067 Uiso 1 1 calc R . . C7A C 0.5077(5) -0.2806(2) 0.1203(3) 0.0668(10) Uani 1 1 d . . . H7A1 H 0.5565 -0.3257 0.0933 0.080 Uiso 1 1 calc R . . H7A2 H 0.3956 -0.2908 0.1530 0.080 Uiso 1 1 calc R . . C8A C 0.6242(5) -0.24915(19) 0.2233(3) 0.0584(9) Uani 1 1 d . . . C9A C 0.5637(5) -0.2354(2) 0.3378(4) 0.0703(11) Uani 1 1 d . . . H9A H 0.4480 -0.2439 0.3521 0.084 Uiso 1 1 calc R . . C10A C 0.6701(7) -0.2093(2) 0.4329(4) 0.0792(13) Uani 1 1 d . . . H10A H 0.6251 -0.1997 0.5097 0.095 Uiso 1 1 calc R . . C11A C 0.8403(7) -0.1976(2) 0.4147(4) 0.0818(13) Uani 1 1 d . . . H11A H 0.9126 -0.1807 0.4788 0.098 Uiso 1 1 calc R . . C12A C 0.9041(6) -0.2112(2) 0.2999(4) 0.0778(12) Uani 1 1 d . . . H12A H 1.0205 -0.2035 0.2868 0.093 Uiso 1 1 calc R . . C13A C 0.7974(5) -0.2361(2) 0.2040(4) 0.0683(10) Uani 1 1 d . . . H13A H 0.8416 -0.2440 0.1264 0.082 Uiso 1 1 calc R . . C14A C 0.1879(5) -0.2869(2) -0.3541(3) 0.0558(9) Uani 1 1 d . . . C15A C 0.1612(6) -0.3615(3) -0.5299(4) 0.0890(14) Uani 1 1 d . . . H15A H 0.1008 -0.4041 -0.5568 0.133 Uiso 1 1 calc R . . H15B H 0.2833 -0.3696 -0.5319 0.133 Uiso 1 1 calc R . . H15C H 0.1298 -0.3223 -0.5839 0.133 Uiso 1 1 calc R . . C16A C -0.2060(5) -0.2605(2) -0.2354(4) 0.0707(11) Uani 1 1 d . . . H16A H -0.2951 -0.2247 -0.2355 0.106 Uiso 1 1 calc R . . H16B H -0.2175 -0.2918 -0.1656 0.106 Uiso 1 1 calc R . . H16C H -0.2161 -0.2880 -0.3104 0.106 Uiso 1 1 calc R . . N1B N 0.3475(3) -0.50712(14) -0.0490(2) 0.0450(6) Uani 1 1 d . . . N2B N 0.3771(4) -0.4721(2) -0.2940(2) 0.0666(8) Uani 1 1 d . . . O1B O 0.0775(3) -0.46764(16) -0.0885(2) 0.0670(7) Uani 1 1 d . . . O2B O 0.3868(4) -0.59023(14) 0.1660(2) 0.0739(8) Uani 1 1 d . . . O3B O 0.2849(3) -0.50101(13) 0.2798(2) 0.0684(7) Uani 1 1 d . . . O4B O 0.6283(3) -0.48026(16) -0.0142(2) 0.0632(6) Uani 1 1 d . . . C1B C 0.1957(4) -0.5195(2) -0.1290(3) 0.0570(9) Uani 1 1 d . . . H1B H 0.1503 -0.5677 -0.1132 0.068 Uiso 1 1 calc R . . C2B C 0.2264(5) -0.5117(2) -0.2655(3) 0.0672(11) Uani 1 1 d . . . H2B1 H 0.2350 -0.5594 -0.3013 0.081 Uiso 1 1 calc R . . H2B2 H 0.1269 -0.4883 -0.3048 0.081 Uiso 1 1 calc R . . C3B C 0.5300(4) -0.50391(18) -0.2262(3) 0.0503(8) Uani 1 1 d . . . H3B H 0.5377 -0.5551 -0.2468 0.060 Uiso 1 1 calc R . . C4B C 0.5101(4) -0.49588(17) -0.0872(3) 0.0463(8) Uani 1 1 d . . . C5B C 0.2941(4) -0.47904(17) 0.0687(3) 0.0450(7) Uani 1 1 d . . . H5B H 0.3513 -0.4330 0.0861 0.054 Uiso 1 1 calc R . . C6B C 0.0970(4) -0.4671(2) 0.0441(3) 0.0555(9) Uani 1 1 d . . . H6B H 0.0330 -0.5074 0.0782 0.067 Uiso 1 1 calc R . . C7B C 0.6875(4) -0.4659(2) -0.2696(3) 0.0638(10) Uani 1 1 d . . . H7B1 H 0.7880 -0.4832 -0.2224 0.077 Uiso 1 1 calc R . . H7B2 H 0.6764 -0.4148 -0.2532 0.077 Uiso 1 1 calc R . . C8B C 0.7159(4) -0.4766(2) -0.4061(3) 0.0533(8) Uani 1 1 d . . . C9B C 0.6884(5) -0.4224(2) -0.4912(3) 0.0669(11) Uani 1 1 d . . . H9B H 0.6556 -0.3773 -0.4636 0.080 Uiso 1 1 calc R . . C10B C 0.7081(6) -0.4330(2) -0.6162(4) 0.0756(12) Uani 1 1 d . . . H10B H 0.6872 -0.3955 -0.6716 0.091 Uiso 1 1 calc R . . C11B C 0.7580(6) -0.4983(3) -0.6582(4) 0.0804(13) Uani 1 1 d . . . H11B H 0.7716 -0.5061 -0.7422 0.096 Uiso 1 1 calc R . . C12B C 0.7874(6) -0.5517(3) -0.5755(4) 0.0911(15) Uani 1 1 d . . . H12B H 0.8218 -0.5964 -0.6038 0.109 Uiso 1 1 calc R . . C13B C 0.7679(5) -0.5420(2) -0.4499(4) 0.0756(12) Uani 1 1 d . . . H13B H 0.7901 -0.5798 -0.3953 0.091 Uiso 1 1 calc R . . C14B C 0.3299(4) -0.5308(2) 0.1748(3) 0.0513(8) Uani 1 1 d . . . C15B C 0.3075(6) -0.5453(3) 0.3903(3) 0.0846(13) Uani 1 1 d . . . H15D H 0.2706 -0.5189 0.4609 0.127 Uiso 1 1 calc R . . H15E H 0.4270 -0.5579 0.4023 0.127 Uiso 1 1 calc R . . H15F H 0.2397 -0.5882 0.3806 0.127 Uiso 1 1 calc R . . C16B C 0.0271(5) -0.3982(2) 0.0910(4) 0.0724(11) Uani 1 1 d . . . H16D H -0.0948 -0.3960 0.0723 0.109 Uiso 1 1 calc R . . H16E H 0.0830 -0.3586 0.0520 0.109 Uiso 1 1 calc R . . H16F H 0.0480 -0.3954 0.1790 0.109 Uiso 1 1 calc R . . HN2A H 0.456(4) -0.124(2) -0.004(3) 0.057(10) Uiso 1 1 d . . . HN2B H 0.343(7) -0.409(3) -0.259(5) 0.15(2) Uiso 1 1 d . . . 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 N1A 0.0615(18) 0.0478(16) 0.0429(15) -0.0081(13) 0.0002(12) -0.0001(15) N2A 0.069(2) 0.0447(17) 0.0544(17) -0.0092(14) 0.0038(14) -0.0024(15) O1A 0.0686(17) 0.0678(16) 0.0615(15) -0.0182(13) 0.0020(12) 0.0043(14) O2A 0.152(3) 0.103(2) 0.0687(19) -0.0208(18) 0.045(2) -0.051(2) O3A 0.0855(18) 0.0686(18) 0.0521(15) -0.0196(13) 0.0029(12) -0.0026(15) O4A 0.0692(17) 0.0558(16) 0.0858(19) -0.0248(14) -0.0096(13) 0.0046(13) C1A 0.066(2) 0.048(2) 0.050(2) -0.0021(16) 0.0009(16) 0.0041(17) C2A 0.070(3) 0.058(2) 0.059(2) -0.0176(18) 0.0034(17) -0.0021(19) C3A 0.064(2) 0.049(2) 0.0491(19) -0.0052(16) 0.0015(15) -0.0107(17) C4A 0.059(2) 0.045(2) 0.0487(19) -0.0032(16) 0.0068(16) -0.0028(17) C5A 0.061(2) 0.0479(19) 0.0424(18) -0.0015(15) 0.0047(15) -0.0035(17) C6A 0.067(2) 0.055(2) 0.0441(19) -0.0081(17) 0.0027(15) -0.0033(18) C7A 0.084(3) 0.051(2) 0.066(2) 0.0079(18) -0.0059(19) -0.010(2) C8A 0.076(3) 0.044(2) 0.054(2) 0.0058(16) -0.0083(18) 0.0001(18) C9A 0.083(3) 0.068(3) 0.060(3) 0.011(2) 0.009(2) -0.008(2) C10A 0.111(4) 0.077(3) 0.050(2) -0.001(2) 0.007(2) -0.003(3) C11A 0.109(4) 0.077(3) 0.058(3) -0.007(2) -0.019(2) -0.001(3) C12A 0.067(3) 0.098(4) 0.068(3) 0.001(2) -0.007(2) 0.000(2) C13A 0.075(3) 0.070(3) 0.060(2) -0.006(2) 0.0029(19) 0.005(2) C14A 0.068(2) 0.055(2) 0.045(2) -0.0062(17) 0.0055(17) -0.0008(19) C15A 0.111(3) 0.104(4) 0.052(2) -0.028(2) -0.003(2) 0.016(3) C16A 0.064(2) 0.077(3) 0.072(3) -0.015(2) 0.0051(18) -0.005(2) N1B 0.0474(15) 0.0527(16) 0.0350(13) -0.0003(12) 0.0033(11) -0.0017(13) N2B 0.0581(19) 0.097(3) 0.0444(16) -0.0016(18) -0.0037(13) -0.0023(19) O1B 0.0522(14) 0.100(2) 0.0488(14) -0.0083(14) 0.0014(10) 0.0061(14) O2B 0.115(2) 0.0547(16) 0.0532(15) 0.0054(13) 0.0147(14) 0.0136(16) O3B 0.1002(19) 0.0662(17) 0.0396(13) 0.0005(12) 0.0122(12) 0.0087(14) O4B 0.0516(14) 0.0923(19) 0.0453(13) 0.0041(13) -0.0032(10) 0.0009(13) C1B 0.055(2) 0.066(2) 0.0505(19) -0.0123(18) 0.0094(16) -0.0121(18) C2B 0.057(2) 0.096(3) 0.049(2) -0.020(2) 0.0052(16) -0.013(2) C3B 0.0499(19) 0.058(2) 0.0434(17) -0.0007(16) 0.0065(14) -0.0007(16) C4B 0.049(2) 0.0464(19) 0.0428(18) 0.0048(15) 0.0000(15) 0.0041(15) C5B 0.0525(18) 0.0407(17) 0.0420(17) -0.0026(14) 0.0052(13) -0.0051(15) C6B 0.054(2) 0.062(2) 0.051(2) -0.0068(18) 0.0109(15) -0.0057(18) C7B 0.057(2) 0.087(3) 0.048(2) 0.002(2) 0.0040(15) -0.006(2) C8B 0.0471(19) 0.065(2) 0.0483(19) 0.0033(18) 0.0088(14) -0.0047(17) C9B 0.086(3) 0.058(2) 0.058(2) -0.0046(19) 0.013(2) -0.015(2) C10B 0.096(3) 0.076(3) 0.056(2) 0.013(2) 0.014(2) -0.009(2) C11B 0.101(3) 0.092(3) 0.050(2) -0.003(2) 0.028(2) -0.008(3) C12B 0.111(4) 0.090(3) 0.074(3) -0.012(3) 0.030(3) 0.033(3) C13B 0.084(3) 0.079(3) 0.065(3) 0.016(2) 0.020(2) 0.024(2) C14B 0.056(2) 0.054(2) 0.0449(19) -0.0025(16) 0.0097(15) -0.0047(17) C15B 0.121(4) 0.095(3) 0.039(2) 0.010(2) 0.012(2) 0.014(3) C16B 0.073(3) 0.080(3) 0.064(2) -0.008(2) 0.0070(19) 0.018(2) _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 N1A C4A 1.339(4) . ? N1A C5A 1.449(4) . ? N1A C1A 1.466(4) . ? N2A C2A 1.451(4) . ? N2A C3A 1.468(4) . ? N2A HN2A 0.94(4) . ? O1A C1A 1.420(4) . ? O1A C6A 1.442(4) . ? O2A C14A 1.198(4) . ? O3A C14A 1.316(4) . ? O3A C15A 1.443(4) . ? O4A C4A 1.225(4) . ? C1A C2A 1.500(4) . ? C1A H1A 0.9800 . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C7A 1.517(5) . ? C3A C4A 1.524(5) . ? C3A H3A 0.9800 . ? C5A C14A 1.505(4) . ? C5A C6A 1.537(5) . ? C5A H5A 0.9800 . ? C6A C16A 1.493(5) . ? C6A H6A 0.9800 . ? C7A C8A 1.523(5) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A C9A 1.364(5) . ? C8A C13A 1.389(5) . ? C9A C10A 1.382(6) . ? C9A H9A 0.9300 . ? C10A C11A 1.360(6) . ? C10A H10A 0.9300 . ? C11A C12A 1.377(6) . ? C11A H11A 0.9300 . ? C12A C13A 1.380(5) . ? C12A H12A 0.9300 . ? C13A H13A 0.9300 . ? C15A H15A 0.9600 . ? C15A H15B 0.9600 . ? C15A H15C 0.9600 . ? C16A H16A 0.9600 . ? C16A H16B 0.9600 . ? C16A H16C 0.9600 . ? N1B C4B 1.359(4) . ? N1B C5B 1.450(4) . ? N1B C1B 1.453(4) . ? N2B C2B 1.426(4) . ? N2B C3B 1.492(4) . ? N2B HN2B 1.27(6) . ? O1B C1B 1.413(4) . ? O1B C6B 1.435(4) . ? O2B C14B 1.195(4) . ? O3B C14B 1.322(4) . ? O3B C15B 1.456(4) . ? O4B C4B 1.221(4) . ? C1B C2B 1.510(4) . ? C1B H1B 0.9800 . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C7B 1.503(4) . ? C3B C4B 1.523(4) . ? C3B H3B 0.9800 . ? C5B C14B 1.515(5) . ? C5B C6B 1.558(4) . ? C5B H5B 0.9800 . ? C6B C16B 1.489(5) . ? C6B H6B 0.9800 . ? C7B C8B 1.514(4) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B C13B 1.372(5) . ? C8B C9B 1.376(5) . ? C9B C10B 1.379(5) . ? C9B H9B 0.9300 . ? C10B C11B 1.359(6) . ? C10B H10B 0.9300 . ? C11B C12B 1.350(6) . ? C11B H11B 0.9300 . ? C12B C13B 1.383(6) . ? C12B H12B 0.9300 . ? C13B H13B 0.9300 . ? C15B H15D 0.9600 . ? C15B H15E 0.9600 . ? C15B H15F 0.9600 . ? C16B H16D 0.9600 . ? C16B H16E 0.9600 . ? C16B H16F 0.9600 . ? 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 C4A N1A C5A 121.9(3) . . ? C4A N1A C1A 125.3(3) . . ? C5A N1A C1A 110.0(3) . . ? C2A N2A C3A 112.9(3) . . ? C2A N2A HN2A 109(2) . . ? C3A N2A HN2A 110(2) . . ? C1A O1A C6A 104.9(2) . . ? C14A O3A C15A 117.2(3) . . ? O1A C1A N1A 102.7(3) . . ? O1A C1A C2A 112.8(3) . . ? N1A C1A C2A 110.1(3) . . ? O1A C1A H1A 110.3 . . ? N1A C1A H1A 110.3 . . ? C2A C1A H1A 110.3 . . ? N2A C2A C1A 109.9(3) . . ? N2A C2A H2A1 109.7 . . ? C1A C2A H2A1 109.7 . . ? N2A C2A H2A2 109.7 . . ? C1A C2A H2A2 109.7 . . ? H2A1 C2A H2A2 108.2 . . ? N2A C3A C7A 111.3(3) . . ? N2A C3A C4A 115.6(3) . . ? C7A C3A C4A 108.8(3) . . ? N2A C3A H3A 106.9 . . ? C7A C3A H3A 106.9 . . ? C4A C3A H3A 106.9 . . ? O4A C4A N1A 121.3(3) . . ? O4A C4A C3A 121.4(3) . . ? N1A C4A C3A 117.3(3) . . ? N1A C5A C14A 113.2(3) . . ? N1A C5A C6A 101.8(3) . . ? C14A C5A C6A 112.0(3) . . ? N1A C5A H5A 109.8 . . ? C14A C5A H5A 109.8 . . ? C6A C5A H5A 109.8 . . ? O1A C6A C16A 109.8(3) . . ? O1A C6A C5A 103.5(3) . . ? C16A C6A C5A 115.5(3) . . ? O1A C6A H6A 109.3 . . ? C16A C6A H6A 109.3 . . ? C5A C6A H6A 109.3 . . ? C3A C7A C8A 113.2(3) . . ? C3A C7A H7A1 108.9 . . ? C8A C7A H7A1 108.9 . . ? C3A C7A H7A2 108.9 . . ? C8A C7A H7A2 108.9 . . ? H7A1 C7A H7A2 107.8 . . ? C9A C8A C13A 118.2(4) . . ? C9A C8A C7A 121.3(4) . . ? C13A C8A C7A 120.5(3) . . ? C8A C9A C10A 121.6(4) . . ? C8A C9A H9A 119.2 . . ? C10A C9A H9A 119.2 . . ? C11A C10A C9A 120.3(4) . . ? C11A C10A H10A 119.9 . . ? C9A C10A H10A 119.9 . . ? C10A C11A C12A 119.1(4) . . ? C10A C11A H11A 120.5 . . ? C12A C11A H11A 120.5 . . ? C11A C12A C13A 120.8(4) . . ? C11A C12A H12A 119.6 . . ? C13A C12A H12A 119.6 . . ? C12A C13A C8A 120.1(4) . . ? C12A C13A H13A 120.0 . . ? C8A C13A H13A 120.0 . . ? O2A C14A O3A 124.8(3) . . ? O2A C14A C5A 124.8(3) . . ? O3A C14A C5A 110.3(3) . . ? O3A C15A H15A 109.5 . . ? O3A C15A H15B 109.5 . . ? H15A C15A H15B 109.5 . . ? O3A C15A H15C 109.5 . . ? H15A C15A H15C 109.5 . . ? H15B C15A H15C 109.5 . . ? C6A C16A H16A 109.5 . . ? C6A C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? C6A C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? C4B N1B C5B 120.7(3) . . ? C4B N1B C1B 125.8(2) . . ? C5B N1B C1B 109.1(2) . . ? C2B N2B C3B 109.3(3) . . ? C2B N2B HN2B 104(3) . . ? C3B N2B HN2B 113(3) . . ? C1B O1B C6B 105.6(3) . . ? C14B O3B C15B 116.1(3) . . ? O1B C1B N1B 103.2(2) . . ? O1B C1B C2B 111.5(3) . . ? N1B C1B C2B 114.3(3) . . ? O1B C1B H1B 109.2 . . ? N1B C1B H1B 109.2 . . ? C2B C1B H1B 109.2 . . ? N2B C2B C1B 115.0(3) . . ? N2B C2B H2B1 108.5 . . ? C1B C2B H2B1 108.5 . . ? N2B C2B H2B2 108.5 . . ? C1B C2B H2B2 108.5 . . ? H2B1 C2B H2B2 107.5 . . ? N2B C3B C7B 107.4(3) . . ? N2B C3B C4B 109.7(2) . . ? C7B C3B C4B 112.1(3) . . ? N2B C3B H3B 109.2 . . ? C7B C3B H3B 109.2 . . ? C4B C3B H3B 109.2 . . ? O4B C4B N1B 121.6(3) . . ? O4B C4B C3B 124.0(3) . . ? N1B C4B C3B 114.5(3) . . ? N1B C5B C14B 112.6(3) . . ? N1B C5B C6B 102.3(2) . . ? C14B C5B C6B 111.7(3) . . ? N1B C5B H5B 110.0 . . ? C14B C5B H5B 110.0 . . ? C6B C5B H5B 110.0 . . ? O1B C6B C16B 108.7(3) . . ? O1B C6B C5B 103.6(2) . . ? C16B C6B C5B 115.7(3) . . ? O1B C6B H6B 109.6 . . ? C16B C6B H6B 109.6 . . ? C5B C6B H6B 109.6 . . ? C3B C7B C8B 113.1(3) . . ? C3B C7B H7B1 109.0 . . ? C8B C7B H7B1 109.0 . . ? C3B C7B H7B2 109.0 . . ? C8B C7B H7B2 109.0 . . ? H7B1 C7B H7B2 107.8 . . ? C13B C8B C9B 117.4(3) . . ? C13B C8B C7B 120.6(3) . . ? C9B C8B C7B 122.0(4) . . ? C8B C9B C10B 122.0(4) . . ? C8B C9B H9B 119.0 . . ? C10B C9B H9B 119.0 . . ? C11B C10B C9B 119.9(4) . . ? C11B C10B H10B 120.1 . . ? C9B C10B H10B 120.1 . . ? C12B C11B C10B 118.7(4) . . ? C12B C11B H11B 120.7 . . ? C10B C11B H11B 120.7 . . ? C11B C12B C13B 122.2(4) . . ? C11B C12B H12B 118.9 . . ? C13B C12B H12B 118.9 . . ? C8B C13B C12B 119.9(4) . . ? C8B C13B H13B 120.1 . . ? C12B C13B H13B 120.1 . . ? O2B C14B O3B 124.5(3) . . ? O2B C14B C5B 125.8(3) . . ? O3B C14B C5B 109.7(3) . . ? O3B C15B H15D 109.5 . . ? O3B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? O3B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C6B C16B H16D 109.5 . . ? C6B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C6B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 70.56 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.367 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.035