# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jian-Wu Xie' _publ_contact_author_email xiejw@zjnu.cn _publ_author_name 'Jian-Wu Xie' data_3ad _database_code_depnum_ccdc_archive 'CCDC 881882' #TrackingRef '- 3ad CCDC 881882.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N O4' _chemical_formula_sum 'C38 H38 N2 O8' _chemical_formula_weight 650.70 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9397(6) _cell_length_b 11.7671(8) _cell_length_c 17.0494(12) _cell_angle_alpha 96.720(3) _cell_angle_beta 97.088(3) _cell_angle_gamma 103.400(3) _cell_volume 1711.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6738 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 27.51 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .32 _exptl_crystal_size_mid .26 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min .0000 _exptl_absorpt_correction_T_max .0000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 27342 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.51 _reflns_number_total 7780 _reflns_number_gt 5106 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens XPREP' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0869P)^2^+0.3028P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0107(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7780 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_ref 0.0842 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1770 _refine_ls_wR_factor_gt 0.1548 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.074 _refine_ls_shift/su_mean 0.009 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 C1 C 1.2137(3) 0.57364(18) 0.28252(12) 0.0575(5) Uani 1 1 d . . . H1A H 1.1868 0.6389 0.2645 0.069 Uiso 1 1 calc R . . C2 C 1.3653(3) 0.5803(2) 0.31324(14) 0.0692(6) Uani 1 1 d . . . H2A H 1.4415 0.6502 0.3165 0.083 Uiso 1 1 calc R . . C3 C 1.4039(3) 0.4825(2) 0.33918(14) 0.0726(7) Uani 1 1 d . . . H3A H 1.5067 0.4867 0.3597 0.087 Uiso 1 1 calc R . . C4 C 1.2921(3) 0.3790(2) 0.33496(13) 0.0643(6) Uani 1 1 d . . . H4A H 1.3200 0.3141 0.3530 0.077 Uiso 1 1 calc R . . C5 C 1.1372(2) 0.36989(17) 0.30397(11) 0.0505(4) Uani 1 1 d . . . C6 C 1.1013(2) 0.46985(16) 0.27852(11) 0.0468(4) Uani 1 1 d . . . C7 C 0.8571(2) 0.35406(14) 0.21326(11) 0.0458(4) Uani 1 1 d . . . C8 C 0.8617(2) 0.26302(15) 0.27171(11) 0.0484(4) Uani 1 1 d . . . H8A H 0.8117 0.1842 0.2418 0.058 Uiso 1 1 calc R . . C9 C 0.7746(2) 0.28287(16) 0.34128(11) 0.0491(4) Uani 1 1 d . . . C10 C 0.6439(3) 0.19810(19) 0.34843(14) 0.0668(6) Uani 1 1 d . . . H10A H 0.6092 0.1310 0.3100 0.080 Uiso 1 1 calc R . . C11 C 0.5634(3) 0.2112(2) 0.41196(16) 0.0817(7) Uani 1 1 d . . . H11A H 0.4750 0.1533 0.4155 0.098 Uiso 1 1 calc R . . C12 C 0.6132(3) 0.3087(3) 0.46934(14) 0.0767(7) Uani 1 1 d . . . H12A H 0.5591 0.3173 0.5120 0.092 Uiso 1 1 calc R . . C13 C 0.7429(3) 0.3935(2) 0.46356(14) 0.0751(7) Uani 1 1 d . . . H13A H 0.7773 0.4602 0.5024 0.090 Uiso 1 1 calc R . . C14 C 0.8232(3) 0.3806(2) 0.40006(13) 0.0650(6) Uani 1 1 d . . . H14A H 0.9117 0.4387 0.3969 0.078 Uiso 1 1 calc R . . C15 C 0.9152(3) 0.31610(18) 0.13411(12) 0.0554(5) Uani 1 1 d . . . C16 C 0.9725(4) 0.4120(2) 0.08687(14) 0.0818(8) Uani 1 1 d . . . H16A H 1.0059 0.3791 0.0399 0.123 Uiso 1 1 calc R . . H16B H 1.0583 0.4702 0.1189 0.123 Uiso 1 1 calc R . . H16C H 0.8899 0.4484 0.0715 0.123 Uiso 1 1 calc R . . C17 C 0.6927(2) 0.36905(17) 0.19179(12) 0.0552(5) Uani 1 1 d . . . C18 C 0.4112(7) 0.2580(5) 0.1460(3) 0.174(3) Uani 1 1 d . . . H18A H 0.3493 0.1781 0.1447 0.209 Uiso 1 1 calc R . . H18B H 0.3828 0.3127 0.1851 0.209 Uiso 1 1 calc R . . C19 C 0.4110(7) 0.2904(7) 0.0771(4) 0.243(4) Uani 1 1 d . . . H19A H 0.3075 0.2930 0.0558 0.364 Uiso 1 1 calc R . . H19B H 0.4452 0.2351 0.0420 0.364 Uiso 1 1 calc R . . H19C H 0.4800 0.3675 0.0817 0.364 Uiso 1 1 calc R . . C20 C 0.5788(3) 0.95945(19) 0.11915(12) 0.0580(5) Uani 1 1 d . . . H20A H 0.6285 1.0376 0.1172 0.070 Uiso 1 1 calc R . . C21 C 0.4270(3) 0.9126(2) 0.08206(14) 0.0726(6) Uani 1 1 d . . . H21A H 0.3738 0.9593 0.0551 0.087 Uiso 1 1 calc R . . C22 C 0.3542(3) 0.7967(2) 0.08501(14) 0.0730(6) Uani 1 1 d . . . H22A H 0.2520 0.7654 0.0599 0.088 Uiso 1 1 calc R . . C23 C 0.4318(3) 0.7262(2) 0.12502(12) 0.0628(5) Uani 1 1 d . . . H23A H 0.3813 0.6480 0.1263 0.075 Uiso 1 1 calc R . . C24 C 0.5854(2) 0.77141(16) 0.16361(10) 0.0483(4) Uani 1 1 d . . . C25 C 0.6563(2) 0.88931(16) 0.15923(10) 0.0459(4) Uani 1 1 d . . . C26 C 0.8999(2) 0.85640(14) 0.20396(10) 0.0418(4) Uani 1 1 d . . . C27 C 0.8230(2) 0.75303(15) 0.24531(10) 0.0443(4) Uani 1 1 d . . . H27A H 0.8796 0.6915 0.2382 0.053 Uiso 1 1 calc R . . C28 C 0.8299(2) 0.78871(16) 0.33462(11) 0.0486(4) Uani 1 1 d . . . C29 C 0.8967(4) 0.7287(3) 0.38733(14) 0.0919(9) Uani 1 1 d . . . H29A H 0.9376 0.6669 0.3681 0.110 Uiso 1 1 calc R . . C30 C 0.9039(5) 0.7591(3) 0.46919(17) 0.1165(12) Uani 1 1 d . . . H30A H 0.9501 0.7176 0.5042 0.140 Uiso 1 1 calc R . . C31 C 0.8446(3) 0.8483(3) 0.49867(14) 0.0871(8) Uani 1 1 d . . . H31A H 0.8497 0.8684 0.5535 0.105 Uiso 1 1 calc R . . C32 C 0.7779(4) 0.9074(3) 0.44668(15) 0.0910(9) Uani 1 1 d . . . H32A H 0.7369 0.9689 0.4661 0.109 Uiso 1 1 calc R . . C33 C 0.7699(3) 0.8778(2) 0.36572(13) 0.0766(7) Uani 1 1 d . . . H33A H 0.7225 0.9193 0.3312 0.092 Uiso 1 1 calc R . . C34 C 1.0573(2) 0.92530(15) 0.25099(11) 0.0454(4) Uani 1 1 d . . . C35 C 1.3122(3) 0.9056(2) 0.29467(13) 0.0651(6) Uani 1 1 d . . . H35A H 1.3439 0.9888 0.2899 0.078 Uiso 1 1 calc R . . H35B H 1.3830 0.8661 0.2707 0.078 Uiso 1 1 calc R . . C36 C 1.3205(3) 0.8920(2) 0.38026(14) 0.0819(7) Uani 1 1 d . . . H36A H 1.4249 0.9261 0.4073 0.123 Uiso 1 1 calc R . . H36B H 1.2913 0.8095 0.3850 0.123 Uiso 1 1 calc R . . H36C H 1.2507 0.9315 0.4040 0.123 Uiso 1 1 calc R . . C37 C 0.9288(2) 0.81119(17) 0.11869(11) 0.0491(4) Uani 1 1 d . . . C38 C 0.9644(3) 0.9028(2) 0.06553(13) 0.0718(6) Uani 1 1 d . . . H38A H 0.9798 0.8664 0.0148 0.108 Uiso 1 1 calc R . . H38B H 1.0572 0.9617 0.0897 0.108 Uiso 1 1 calc R . . H38C H 0.8791 0.9392 0.0579 0.108 Uiso 1 1 calc R . . N1 N 1.0224(2) 0.26666(14) 0.29866(11) 0.0597(4) Uani 1 1 d . . . H1B H 1.0470 0.2041 0.3115 0.072 Uiso 1 1 calc R . . N2 N 0.66590(19) 0.70521(14) 0.20419(10) 0.0551(4) Uani 1 1 d . . . H2B H 0.6213 0.6324 0.2052 0.066 Uiso 1 1 calc R . . O1 O 0.94852(15) 0.46859(10) 0.24885(8) 0.0489(3) Uani 1 1 d . . . O2 O 0.6556(2) 0.45852(14) 0.20681(12) 0.0840(5) Uani 1 1 d . . . O3 O 0.5987(2) 0.26843(15) 0.15616(13) 0.0903(6) Uani 1 1 d . . . O4 O 0.9101(2) 0.21476(14) 0.11284(10) 0.0846(5) Uani 1 1 d . . . O5 O 0.80813(14) 0.94000(10) 0.19736(7) 0.0468(3) Uani 1 1 d . . . O6 O 1.09015(18) 1.02661(12) 0.28072(10) 0.0705(4) Uani 1 1 d . . . O7 O 1.15489(15) 0.85561(11) 0.25268(8) 0.0543(3) Uani 1 1 d . . . O8 O 0.9260(2) 0.70975(13) 0.09924(9) 0.0733(5) Uani 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 C1 0.0630(13) 0.0479(11) 0.0606(12) 0.0027(9) 0.0165(10) 0.0108(9) C2 0.0563(14) 0.0735(15) 0.0718(14) 0.0012(11) 0.0166(11) 0.0058(11) C3 0.0503(13) 0.1005(19) 0.0675(14) 0.0025(13) 0.0109(11) 0.0244(13) C4 0.0626(14) 0.0784(15) 0.0615(12) 0.0122(11) 0.0149(11) 0.0333(12) C5 0.0564(12) 0.0516(11) 0.0495(10) 0.0059(8) 0.0156(9) 0.0224(9) C6 0.0507(11) 0.0437(10) 0.0474(9) 0.0021(7) 0.0112(8) 0.0150(8) C7 0.0551(11) 0.0311(8) 0.0509(10) 0.0038(7) 0.0090(8) 0.0111(7) C8 0.0582(12) 0.0335(9) 0.0552(10) 0.0061(7) 0.0115(9) 0.0138(8) C9 0.0580(12) 0.0430(10) 0.0493(10) 0.0114(8) 0.0085(9) 0.0162(8) C10 0.0768(15) 0.0536(12) 0.0690(13) 0.0110(10) 0.0193(12) 0.0094(11) C11 0.0878(18) 0.0758(16) 0.0860(17) 0.0237(14) 0.0367(14) 0.0116(13) C12 0.0858(18) 0.0955(19) 0.0614(13) 0.0233(13) 0.0277(13) 0.0335(15) C13 0.0841(17) 0.0850(17) 0.0540(12) -0.0044(11) 0.0097(12) 0.0244(14) C14 0.0659(14) 0.0612(13) 0.0616(12) -0.0033(10) 0.0109(11) 0.0094(10) C15 0.0666(13) 0.0487(11) 0.0524(10) 0.0052(8) 0.0123(9) 0.0166(9) C16 0.122(2) 0.0646(14) 0.0600(13) 0.0139(11) 0.0311(14) 0.0150(14) C17 0.0581(12) 0.0450(11) 0.0643(12) 0.0114(9) 0.0097(10) 0.0152(9) C18 0.218(6) 0.212(5) 0.105(3) -0.047(3) -0.038(3) 0.144(5) C19 0.161(5) 0.308(9) 0.201(7) -0.100(7) 0.073(5) -0.013(5) C20 0.0632(13) 0.0602(12) 0.0566(11) 0.0110(9) 0.0063(10) 0.0277(10) C21 0.0711(16) 0.0862(17) 0.0664(14) 0.0134(12) 0.0012(12) 0.0356(14) C22 0.0565(13) 0.0939(19) 0.0639(13) 0.0008(12) -0.0003(11) 0.0197(13) C23 0.0610(14) 0.0654(13) 0.0571(12) 0.0009(10) 0.0119(10) 0.0089(10) C24 0.0528(11) 0.0497(10) 0.0429(9) 0.0024(8) 0.0118(8) 0.0140(9) C25 0.0509(11) 0.0471(10) 0.0421(9) 0.0034(7) 0.0092(8) 0.0179(8) C26 0.0499(10) 0.0338(8) 0.0460(9) 0.0075(7) 0.0116(8) 0.0158(7) C27 0.0524(11) 0.0362(9) 0.0490(9) 0.0093(7) 0.0142(8) 0.0155(8) C28 0.0539(11) 0.0476(10) 0.0486(10) 0.0130(8) 0.0166(8) 0.0138(8) C29 0.149(3) 0.098(2) 0.0629(14) 0.0356(13) 0.0371(16) 0.077(2) C30 0.184(4) 0.142(3) 0.0597(15) 0.0473(17) 0.0329(19) 0.091(3) C31 0.105(2) 0.117(2) 0.0457(12) 0.0129(13) 0.0221(13) 0.0347(18) C32 0.120(2) 0.111(2) 0.0570(14) -0.0006(14) 0.0221(14) 0.0598(19) C33 0.105(2) 0.0908(17) 0.0503(12) 0.0066(11) 0.0124(12) 0.0591(16) C34 0.0541(11) 0.0368(9) 0.0486(9) 0.0091(7) 0.0112(8) 0.0146(8) C35 0.0537(13) 0.0696(14) 0.0691(13) -0.0007(11) 0.0030(10) 0.0190(11) C36 0.0961(19) 0.0773(16) 0.0652(14) -0.0047(12) -0.0075(13) 0.0258(14) C37 0.0541(11) 0.0488(11) 0.0456(9) 0.0064(8) 0.0104(8) 0.0146(8) C38 0.0946(18) 0.0736(15) 0.0588(12) 0.0260(11) 0.0310(12) 0.0267(13) N1 0.0640(11) 0.0447(9) 0.0784(11) 0.0166(8) 0.0115(9) 0.0255(8) N2 0.0582(10) 0.0389(8) 0.0651(10) 0.0120(7) 0.0079(8) 0.0049(7) O1 0.0549(8) 0.0323(6) 0.0595(7) 0.0037(5) 0.0073(6) 0.0129(5) O2 0.0711(11) 0.0548(9) 0.1314(15) 0.0085(9) 0.0137(10) 0.0302(8) O3 0.0629(11) 0.0625(10) 0.1286(16) -0.0086(10) -0.0237(10) 0.0137(8) O4 0.1365(16) 0.0517(9) 0.0772(10) 0.0047(7) 0.0469(11) 0.0335(9) O5 0.0509(8) 0.0358(6) 0.0565(7) 0.0087(5) 0.0069(6) 0.0163(5) O6 0.0726(10) 0.0381(8) 0.0935(11) -0.0043(7) -0.0062(8) 0.0164(7) O7 0.0510(8) 0.0491(7) 0.0622(8) -0.0002(6) 0.0038(6) 0.0182(6) O8 0.1137(14) 0.0511(9) 0.0602(9) 0.0015(7) 0.0315(9) 0.0245(8) _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 C1 C2 1.372(3) . ? C1 C6 1.379(3) . ? C1 H1A 0.9300 . ? C2 C3 1.380(4) . ? C2 H2A 0.9300 . ? C3 C4 1.373(3) . ? C3 H3A 0.9300 . ? C4 C5 1.394(3) . ? C4 H4A 0.9300 . ? C5 N1 1.382(3) . ? C5 C6 1.391(3) . ? C6 O1 1.393(2) . ? C7 O1 1.424(2) . ? C7 C17 1.526(3) . ? C7 C8 1.550(2) . ? C7 C15 1.559(3) . ? C8 N1 1.443(3) . ? C8 C9 1.521(3) . ? C8 H8A 0.9800 . ? C9 C10 1.378(3) . ? C9 C14 1.381(3) . ? C10 C11 1.386(3) . ? C10 H10A 0.9300 . ? C11 C12 1.365(4) . ? C11 H11A 0.9300 . ? C12 C13 1.366(4) . ? C12 H12A 0.9300 . ? C13 C14 1.384(3) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 O4 1.194(2) . ? C15 C16 1.494(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O2 1.185(2) . ? C17 O3 1.312(2) . ? C18 C19 1.277(8) . ? C18 O3 1.638(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.380(3) . ? C20 C25 1.381(3) . ? C20 H20A 0.9300 . ? C21 C22 1.379(4) . ? C21 H21A 0.9300 . ? C22 C23 1.384(3) . ? C22 H22A 0.9300 . ? C23 C24 1.399(3) . ? C23 H23A 0.9300 . ? C24 N2 1.366(2) . ? C24 C25 1.400(3) . ? C25 O5 1.392(2) . ? C26 O5 1.4252(19) . ? C26 C34 1.523(3) . ? C26 C27 1.543(2) . ? C26 C37 1.562(2) . ? C27 N2 1.442(2) . ? C27 C28 1.521(2) . ? C27 H27A 0.9800 . ? C28 C33 1.368(3) . ? C28 C29 1.369(3) . ? C29 C30 1.389(4) . ? C29 H29A 0.9300 . ? C30 C31 1.355(4) . ? C30 H30A 0.9300 . ? C31 C32 1.354(4) . ? C31 H31A 0.9300 . ? C32 C33 1.372(3) . ? C32 H32A 0.9300 . ? C33 H33A 0.9300 . ? C34 O6 1.193(2) . ? C34 O7 1.329(2) . ? C35 O7 1.451(2) . ? C35 C36 1.481(3) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 O8 1.195(2) . ? C37 C38 1.492(3) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? N1 H1B 0.8600 . ? N2 H2B 0.8600 . ? 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 C1 C6 119.8(2) . . ? C2 C1 H1A 120.1 . . ? C6 C1 H1A 120.1 . . ? C1 C2 C3 119.6(2) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 120.9(2) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? N1 C5 C6 120.56(18) . . ? N1 C5 C4 122.13(18) . . ? C6 C5 C4 117.30(19) . . ? C1 C6 C5 121.79(19) . . ? C1 C6 O1 117.55(16) . . ? C5 C6 O1 120.65(17) . . ? O1 C7 C17 105.15(14) . . ? O1 C7 C8 111.26(15) . . ? C17 C7 C8 111.42(15) . . ? O1 C7 C15 109.27(14) . . ? C17 C7 C15 107.97(16) . . ? C8 C7 C15 111.52(14) . . ? N1 C8 C9 111.88(16) . . ? N1 C8 C7 108.25(15) . . ? C9 C8 C7 112.86(14) . . ? N1 C8 H8A 107.9 . . ? C9 C8 H8A 107.9 . . ? C7 C8 H8A 107.9 . . ? C10 C9 C14 117.63(19) . . ? C10 C9 C8 119.18(17) . . ? C14 C9 C8 123.15(18) . . ? C9 C10 C11 121.1(2) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C11 C12 C13 119.5(2) . . ? C11 C12 H12A 120.3 . . ? C13 C12 H12A 120.3 . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13A 119.9 . . ? C14 C13 H13A 119.9 . . ? C9 C14 C13 121.3(2) . . ? C9 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? O4 C15 C16 122.9(2) . . ? O4 C15 C7 120.55(17) . . ? C16 C15 C7 116.49(17) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 O3 125.3(2) . . ? O2 C17 C7 124.46(19) . . ? O3 C17 C7 110.24(16) . . ? C19 C18 O3 91.5(6) . . ? C19 C18 H18A 113.4 . . ? O3 C18 H18A 113.4 . . ? C19 C18 H18B 113.4 . . ? O3 C18 H18B 113.4 . . ? H18A C18 H18B 110.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 119.4(2) . . ? C21 C20 H20A 120.3 . . ? C25 C20 H20A 120.3 . . ? C22 C21 C20 120.0(2) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C23 120.7(2) . . ? C21 C22 H22A 119.7 . . ? C23 C22 H22A 119.7 . . ? C22 C23 C24 120.7(2) . . ? C22 C23 H23A 119.7 . . ? C24 C23 H23A 119.7 . . ? N2 C24 C23 122.57(18) . . ? N2 C24 C25 120.14(17) . . ? C23 C24 C25 117.28(18) . . ? C20 C25 O5 117.95(17) . . ? C20 C25 C24 121.98(19) . . ? O5 C25 C24 120.06(16) . . ? O5 C26 C34 105.89(13) . . ? O5 C26 C27 111.92(14) . . ? C34 C26 C27 111.71(14) . . ? O5 C26 C37 108.74(13) . . ? C34 C26 C37 106.97(14) . . ? C27 C26 C37 111.33(14) . . ? N2 C27 C28 112.59(15) . . ? N2 C27 C26 107.79(14) . . ? C28 C27 C26 112.82(14) . . ? N2 C27 H27A 107.8 . . ? C28 C27 H27A 107.8 . . ? C26 C27 H27A 107.8 . . ? C33 C28 C29 117.48(19) . . ? C33 C28 C27 123.08(17) . . ? C29 C28 C27 119.43(18) . . ? C28 C29 C30 120.6(2) . . ? C28 C29 H29A 119.7 . . ? C30 C29 H29A 119.7 . . ? C31 C30 C29 120.9(3) . . ? C31 C30 H30A 119.6 . . ? C29 C30 H30A 119.6 . . ? C32 C31 C30 118.6(2) . . ? C32 C31 H31A 120.7 . . ? C30 C31 H31A 120.7 . . ? C31 C32 C33 120.9(2) . . ? C31 C32 H32A 119.5 . . ? C33 C32 H32A 119.5 . . ? C28 C33 C32 121.5(2) . . ? C28 C33 H33A 119.3 . . ? C32 C33 H33A 119.3 . . ? O6 C34 O7 124.70(18) . . ? O6 C34 C26 125.90(17) . . ? O7 C34 C26 109.39(14) . . ? O7 C35 C36 110.4(2) . . ? O7 C35 H35A 109.6 . . ? C36 C35 H35A 109.6 . . ? O7 C35 H35B 109.6 . . ? C36 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O8 C37 C38 123.15(18) . . ? O8 C37 C26 121.02(16) . . ? C38 C37 C26 115.81(16) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C5 N1 C8 120.56(15) . . ? C5 N1 H1B 119.7 . . ? C8 N1 H1B 119.7 . . ? C24 N2 C27 122.31(15) . . ? C24 N2 H2B 118.8 . . ? C27 N2 H2B 118.8 . . ? C6 O1 C7 113.14(13) . . ? C17 O3 C18 117.7(2) . . ? C25 O5 C26 113.12(13) . . ? C34 O7 C35 117.75(15) . . ? 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 C6 C1 C2 C3 0.6(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 N1 179.70(19) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C2 C1 C6 C5 -0.8(3) . . . . ? C2 C1 C6 O1 178.33(17) . . . . ? N1 C5 C6 C1 -179.47(17) . . . . ? C4 C5 C6 C1 0.8(3) . . . . ? N1 C5 C6 O1 1.4(3) . . . . ? C4 C5 C6 O1 -178.29(16) . . . . ? O1 C7 C8 N1 -54.44(19) . . . . ? C17 C7 C8 N1 -171.42(15) . . . . ? C15 C7 C8 N1 67.85(19) . . . . ? O1 C7 C8 C9 70.0(2) . . . . ? C17 C7 C8 C9 -47.0(2) . . . . ? C15 C7 C8 C9 -167.76(16) . . . . ? N1 C8 C9 C10 -122.4(2) . . . . ? C7 C8 C9 C10 115.2(2) . . . . ? N1 C8 C9 C14 55.2(2) . . . . ? C7 C8 C9 C14 -67.2(2) . . . . ? C14 C9 C10 C11 0.7(3) . . . . ? C8 C9 C10 C11 178.4(2) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ? C10 C9 C14 C13 -0.6(3) . . . . ? C8 C9 C14 C13 -178.2(2) . . . . ? C12 C13 C14 C9 0.3(4) . . . . ? O1 C7 C15 O4 146.8(2) . . . . ? C17 C7 C15 O4 -99.3(2) . . . . ? C8 C7 C15 O4 23.4(3) . . . . ? O1 C7 C15 C16 -34.6(3) . . . . ? C17 C7 C15 C16 79.3(2) . . . . ? C8 C7 C15 C16 -158.0(2) . . . . ? O1 C7 C17 O2 -3.2(3) . . . . ? C8 C7 C17 O2 117.5(2) . . . . ? C15 C7 C17 O2 -119.7(2) . . . . ? O1 C7 C17 O3 178.19(17) . . . . ? C8 C7 C17 O3 -61.2(2) . . . . ? C15 C7 C17 O3 61.6(2) . . . . ? C25 C20 C21 C22 -0.2(3) . . . . ? C20 C21 C22 C23 0.1(4) . . . . ? C21 C22 C23 C24 0.3(3) . . . . ? C22 C23 C24 N2 179.57(19) . . . . ? C22 C23 C24 C25 -0.6(3) . . . . ? C21 C20 C25 O5 -178.71(17) . . . . ? C21 C20 C25 C24 -0.1(3) . . . . ? N2 C24 C25 C20 -179.69(17) . . . . ? C23 C24 C25 C20 0.4(3) . . . . ? N2 C24 C25 O5 -1.1(2) . . . . ? C23 C24 C25 O5 179.06(16) . . . . ? O5 C26 C27 N2 52.38(18) . . . . ? C34 C26 C27 N2 170.93(14) . . . . ? C37 C26 C27 N2 -69.56(18) . . . . ? O5 C26 C27 C28 -72.56(19) . . . . ? C34 C26 C27 C28 46.0(2) . . . . ? C37 C26 C27 C28 165.51(15) . . . . ? N2 C27 C28 C33 -65.1(3) . . . . ? C26 C27 C28 C33 57.2(3) . . . . ? N2 C27 C28 C29 113.8(2) . . . . ? C26 C27 C28 C29 -123.9(2) . . . . ? C33 C28 C29 C30 -0.7(4) . . . . ? C27 C28 C29 C30 -179.7(3) . . . . ? C28 C29 C30 C31 0.3(6) . . . . ? C29 C30 C31 C32 0.0(6) . . . . ? C30 C31 C32 C33 0.1(5) . . . . ? C29 C28 C33 C32 0.9(4) . . . . ? C27 C28 C33 C32 179.8(2) . . . . ? C31 C32 C33 C28 -0.6(5) . . . . ? O5 C26 C34 O6 5.0(2) . . . . ? C27 C26 C34 O6 -117.1(2) . . . . ? C37 C26 C34 O6 120.9(2) . . . . ? O5 C26 C34 O7 -173.73(13) . . . . ? C27 C26 C34 O7 64.18(18) . . . . ? C37 C26 C34 O7 -57.88(17) . . . . ? O5 C26 C37 O8 -140.59(19) . . . . ? C34 C26 C37 O8 105.5(2) . . . . ? C27 C26 C37 O8 -16.8(3) . . . . ? O5 C26 C37 C38 41.3(2) . . . . ? C34 C26 C37 C38 -72.7(2) . . . . ? C27 C26 C37 C38 165.03(18) . . . . ? C6 C5 N1 C8 -4.2(3) . . . . ? C4 C5 N1 C8 175.46(18) . . . . ? C9 C8 N1 C5 -95.4(2) . . . . ? C7 C8 N1 C5 29.6(2) . . . . ? C23 C24 N2 C27 -178.61(17) . . . . ? C25 C24 N2 C27 1.5(3) . . . . ? C28 C27 N2 C24 98.87(19) . . . . ? C26 C27 N2 C24 -26.2(2) . . . . ? C1 C6 O1 C7 153.06(16) . . . . ? C5 C6 O1 C7 -27.8(2) . . . . ? C17 C7 O1 C6 174.97(14) . . . . ? C8 C7 O1 C6 54.23(19) . . . . ? C15 C7 O1 C6 -69.35(18) . . . . ? O2 C17 O3 C18 -11.8(4) . . . . ? C7 C17 O3 C18 166.8(3) . . . . ? C19 C18 O3 C17 92.3(4) . . . . ? C20 C25 O5 C26 -152.64(16) . . . . ? C24 C25 O5 C26 28.7(2) . . . . ? C34 C26 O5 C25 -176.70(13) . . . . ? C27 C26 O5 C25 -54.75(18) . . . . ? C37 C26 O5 C25 68.65(17) . . . . ? O6 C34 O7 C35 1.0(3) . . . . ? C26 C34 O7 C35 179.71(15) . . . . ? C36 C35 O7 C34 88.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.495 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.037 _publ_section_references ; Sheldrick G.M.(1996), SADABS, Absorption Correction Program, University of Goeltingen, German Siemens(1994), SAINT Software Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA Siemens(1996), SMART Software Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA Siemens(1994), SHELXTL^TM^ Version 5 Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA ; # Attachment '- 3ha CCDC 881883.CIF' data_3ha _database_code_depnum_ccdc_archive 'CCDC 881883' #TrackingRef '- 3ha CCDC 881883.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 Cl N O5' _chemical_formula_sum 'C20 H20 Cl N O5' _chemical_formula_weight 389.82 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(3) _symmetry_space_group_name_Hall 'P 4cw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 9.0853(7) _cell_length_b 9.0853(7) _cell_length_c 23.592(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1947.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2175 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.46 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .46 _exptl_crystal_size_mid .38 _exptl_crystal_size_min .28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min .90 _exptl_absorpt_correction_T_max .94 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEXII area-detector diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 8605 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3959 _reflns_number_gt 2481 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEXII (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material SHELXTL _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^)+(0.0989P)^2^+0.2496P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.005(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.74(14) _chemical_absolute_configuration syn _refine_ls_number_reflns 3959 _refine_ls_number_parameters 246 _refine_ls_number_restraints 2 _refine_ls_R_factor_ref 0.0991 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1862 _refine_ls_wR_factor_gt 0.1586 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 0.1367(2) 0.65274(19) 0.22227(6) 0.1124(6) Uani 1 1 d . . . C1 C -0.0446(4) 0.8404(4) 0.13711(16) 0.0592(9) Uani 1 1 d . . . H1A H -0.0720 0.7622 0.1637 0.071 Uiso 1 1 calc R . . C2 C -0.0874(4) 0.7923(4) 0.07712(15) 0.0529(8) Uani 1 1 d . . . C3 C -0.1489(4) 1.0341(4) 0.05244(17) 0.0545(9) Uani 1 1 d . . . C4 C -0.1892(5) 1.1283(6) 0.0090(2) 0.0767(12) Uani 1 1 d . . . H4A H -0.1676 1.1062 -0.0286 0.092 Uiso 1 1 calc R . . C5 C -0.2629(7) 1.2565(7) 0.0234(3) 0.0992(17) Uani 1 1 d . . . H5A H -0.2896 1.3228 -0.0048 0.119 Uiso 1 1 calc R . . C6 C -0.2967(7) 1.2866(6) 0.0787(3) 0.0965(17) Uani 1 1 d . . . H6A H -0.3495 1.3712 0.0875 0.116 Uiso 1 1 calc R . . C7 C -0.2541(5) 1.1947(5) 0.1208(2) 0.0743(12) Uani 1 1 d . . . H7A H -0.2758 1.2181 0.1582 0.089 Uiso 1 1 calc R . . C8 C -0.1774(4) 1.0639(4) 0.10841(17) 0.0562(9) Uani 1 1 d . . . C9 C 0.1202(4) 0.8695(5) 0.14261(16) 0.0586(9) Uani 1 1 d . . . C10 C 0.2109(6) 0.7895(5) 0.17891(18) 0.0731(12) Uani 1 1 d . . . C11 C 0.3607(6) 0.8175(7) 0.1834(2) 0.0906(16) Uani 1 1 d . . . H11A H 0.4181 0.7609 0.2077 0.109 Uiso 1 1 calc R . . C12 C 0.4242(6) 0.9265(7) 0.1527(2) 0.0871(15) Uani 1 1 d . . . H12A H 0.5247 0.9449 0.1553 0.105 Uiso 1 1 calc R . . C13 C 0.3380(5) 1.0069(6) 0.1186(2) 0.0778(12) Uani 1 1 d . . . H13A H 0.3796 1.0838 0.0981 0.093 Uiso 1 1 calc R . . C14 C 0.1912(5) 0.9794(5) 0.11299(19) 0.0687(11) Uani 1 1 d . . . H14A H 0.1366 1.0372 0.0882 0.082 Uiso 1 1 calc R . . C15 C 0.0114(5) 0.6673(5) 0.05582(17) 0.0608(10) Uani 1 1 d . . . C16 C 0.0881(7) 0.4236(6) 0.0793(3) 0.0968(17) Uani 1 1 d . . . H16A H 0.0456 0.3424 0.1004 0.116 Uiso 1 1 calc R . . H16B H 0.0786 0.4019 0.0392 0.116 Uiso 1 1 calc R . . C17 C 0.2418(8) 0.4370(8) 0.0936(4) 0.129(3) Uani 1 1 d . . . H17A H 0.2918 0.3471 0.0843 0.193 Uiso 1 1 calc R . . H17B H 0.2516 0.4561 0.1334 0.193 Uiso 1 1 calc R . . H17C H 0.2843 0.5167 0.0725 0.193 Uiso 1 1 calc R . . C18 C -0.2453(5) 0.7306(5) 0.0767(2) 0.0691(11) Uani 1 1 d . . . C19 C -0.4505(9) 0.6742(11) 0.0230(5) 0.163(4) Uani 1 1 d D . . H19A H -0.4519 0.5676 0.0209 0.196 Uiso 1 1 calc R . . H19B H -0.5024 0.7035 0.0571 0.196 Uiso 1 1 calc R . . C20 C -0.5149(10) 0.7265(18) -0.0195(6) 0.335(14) Uani 1 1 d D . . H20A H -0.6144 0.6912 -0.0206 0.503 Uiso 1 1 calc R . . H20B H -0.4644 0.6964 -0.0534 0.503 Uiso 1 1 calc R . . H20C H -0.5152 0.8320 -0.0172 0.503 Uiso 1 1 calc R . . N1 N -0.1308(4) 0.9726(4) 0.15054(14) 0.0678(9) Uani 1 1 d . . . H1B H -0.1519 0.9925 0.1852 0.081 Uiso 1 1 calc R . . O1 O -0.0728(3) 0.9078(3) 0.03689(11) 0.0571(6) Uani 1 1 d . . . O2 O 0.0076(4) 0.5583(3) 0.09233(13) 0.0729(8) Uani 1 1 d . . . O3 O 0.0783(4) 0.6698(3) 0.01234(13) 0.0793(9) Uani 1 1 d . . . O4 O -0.3097(4) 0.6912(4) 0.1176(2) 0.1007(12) Uani 1 1 d . . . O5 O -0.2965(4) 0.7260(6) 0.02597(18) 0.1122(14) Uani 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 Cl1 0.1438(13) 0.1236(12) 0.0699(8) 0.0419(8) -0.0180(8) 0.0045(10) C1 0.072(2) 0.065(2) 0.0410(19) 0.0035(16) 0.0094(17) 0.0103(18) C2 0.060(2) 0.056(2) 0.0427(18) -0.0003(15) 0.0048(15) 0.0014(16) C3 0.052(2) 0.056(2) 0.055(2) 0.0017(16) -0.0040(16) 0.0011(16) C4 0.080(3) 0.081(3) 0.069(3) 0.016(2) -0.011(2) 0.008(2) C5 0.108(4) 0.090(4) 0.099(5) 0.024(3) -0.009(3) 0.030(3) C6 0.095(4) 0.070(3) 0.124(5) 0.002(3) -0.006(3) 0.025(3) C7 0.072(3) 0.069(3) 0.082(3) -0.009(2) 0.006(2) 0.018(2) C8 0.052(2) 0.058(2) 0.059(2) -0.0006(17) 0.0004(17) 0.0024(16) C9 0.067(2) 0.073(2) 0.0357(17) -0.0123(17) 0.0014(16) 0.0116(19) C10 0.093(3) 0.086(3) 0.041(2) -0.0018(19) -0.010(2) 0.010(2) C11 0.092(4) 0.111(4) 0.068(3) -0.002(3) -0.030(3) 0.025(3) C12 0.078(3) 0.118(4) 0.065(3) -0.008(3) -0.013(2) 0.003(3) C13 0.067(3) 0.095(3) 0.071(3) -0.003(2) -0.007(2) -0.004(2) C14 0.074(3) 0.079(3) 0.054(2) 0.007(2) -0.004(2) 0.007(2) C15 0.064(2) 0.069(2) 0.050(2) -0.0099(18) 0.0005(18) 0.0004(19) C16 0.121(5) 0.071(3) 0.099(4) -0.008(3) 0.018(3) 0.021(3) C17 0.114(5) 0.109(5) 0.163(8) -0.016(5) 0.000(5) 0.030(4) C18 0.059(2) 0.067(3) 0.081(3) -0.004(2) 0.006(2) -0.002(2) C19 0.097(5) 0.207(9) 0.186(10) 0.042(7) -0.051(6) -0.051(5) C20 0.084(5) 0.67(4) 0.256(18) 0.26(2) -0.059(7) -0.078(11) N1 0.081(2) 0.077(2) 0.0455(18) -0.0027(15) 0.0122(16) 0.0229(19) O1 0.0663(15) 0.0619(15) 0.0432(13) 0.0031(11) 0.0042(11) 0.0032(12) O2 0.088(2) 0.0601(17) 0.0703(19) 0.0024(14) 0.0130(15) 0.0181(15) O3 0.098(2) 0.084(2) 0.0557(18) -0.0094(14) 0.0201(16) 0.0108(17) O4 0.078(2) 0.115(3) 0.109(3) 0.020(2) 0.028(2) -0.0125(19) O5 0.087(2) 0.155(4) 0.094(3) 0.017(3) -0.024(2) -0.047(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 Cl1 C10 1.745(5) . ? C1 N1 1.468(5) . ? C1 C9 1.526(6) . ? C1 C2 1.531(5) . ? C1 H1A 0.9800 . ? C2 O1 1.421(4) . ? C2 C15 1.533(5) . ? C2 C18 1.540(6) . ? C3 C8 1.373(6) . ? C3 C4 1.384(6) . ? C3 O1 1.389(5) . ? C4 C5 1.386(8) . ? C4 H4A 0.9300 . ? C5 C6 1.367(9) . ? C5 H5A 0.9300 . ? C6 C7 1.354(8) . ? C6 H6A 0.9300 . ? C7 C8 1.408(6) . ? C7 H7A 0.9300 . ? C8 N1 1.362(5) . ? C9 C14 1.379(6) . ? C9 C10 1.393(6) . ? C10 C11 1.389(8) . ? C11 C12 1.355(8) . ? C11 H11A 0.9300 . ? C12 C13 1.340(8) . ? C12 H12A 0.9300 . ? C13 C14 1.364(6) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 O3 1.193(5) . ? C15 O2 1.312(5) . ? C16 C17 1.441(10) . ? C16 O2 1.459(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 O4 1.184(6) . ? C18 O5 1.284(6) . ? C19 C20 1.255(12) . ? C19 O5 1.478(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 H1B 0.8600 . ? 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 N1 C1 C9 111.3(3) . . ? N1 C1 C2 107.3(3) . . ? C9 C1 C2 112.2(3) . . ? N1 C1 H1A 108.7 . . ? C9 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? O1 C2 C1 112.5(3) . . ? O1 C2 C15 105.9(3) . . ? C1 C2 C15 111.4(3) . . ? O1 C2 C18 110.6(3) . . ? C1 C2 C18 110.3(3) . . ? C15 C2 C18 105.9(3) . . ? C8 C3 C4 122.7(4) . . ? C8 C3 O1 120.7(3) . . ? C4 C3 O1 116.6(4) . . ? C3 C4 C5 117.8(5) . . ? C3 C4 H4A 121.1 . . ? C5 C4 H4A 121.1 . . ? C6 C5 C4 120.7(5) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C7 C6 C5 120.8(5) . . ? C7 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C6 C7 C8 120.7(5) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? N1 C8 C3 121.5(3) . . ? N1 C8 C7 121.1(4) . . ? C3 C8 C7 117.3(4) . . ? C14 C9 C10 114.4(4) . . ? C14 C9 C1 122.8(4) . . ? C10 C9 C1 122.9(4) . . ? C11 C10 C9 122.1(5) . . ? C11 C10 Cl1 117.7(4) . . ? C9 C10 Cl1 120.2(4) . . ? C12 C11 C10 120.7(4) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C13 C12 C11 118.1(5) . . ? C13 C12 H12A 121.0 . . ? C11 C12 H12A 121.0 . . ? C12 C13 C14 122.0(5) . . ? C12 C13 H13A 119.0 . . ? C14 C13 H13A 119.0 . . ? C13 C14 C9 122.8(4) . . ? C13 C14 H14A 118.6 . . ? C9 C14 H14A 118.6 . . ? O3 C15 O2 126.3(4) . . ? O3 C15 C2 124.5(4) . . ? O2 C15 C2 109.2(3) . . ? C17 C16 O2 111.5(5) . . ? C17 C16 H16A 109.3 . . ? O2 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? O2 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 O5 124.8(5) . . ? O4 C18 C2 124.4(5) . . ? O5 C18 C2 110.8(4) . . ? C20 C19 O5 111.0(8) . . ? C20 C19 H19A 109.4 . . ? O5 C19 H19A 109.4 . . ? C20 C19 H19B 109.4 . . ? O5 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C8 N1 C1 120.4(3) . . ? C8 N1 H1B 119.8 . . ? C1 N1 H1B 119.8 . . ? C3 O1 C2 112.8(3) . . ? C15 O2 C16 118.8(4) . . ? C18 O5 C19 113.4(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 N1 C1 C2 O1 53.6(4) . . . . ? C9 C1 C2 O1 -68.9(4) . . . . ? N1 C1 C2 C15 172.3(3) . . . . ? C9 C1 C2 C15 49.8(4) . . . . ? N1 C1 C2 C18 -70.4(4) . . . . ? C9 C1 C2 C18 167.1(3) . . . . ? C8 C3 C4 C5 -0.8(7) . . . . ? O1 C3 C4 C5 -178.8(4) . . . . ? C3 C4 C5 C6 -1.3(8) . . . . ? C4 C5 C6 C7 2.5(10) . . . . ? C5 C6 C7 C8 -1.7(9) . . . . ? C4 C3 C8 N1 -177.0(4) . . . . ? O1 C3 C8 N1 0.9(6) . . . . ? C4 C3 C8 C7 1.6(6) . . . . ? O1 C3 C8 C7 179.5(3) . . . . ? C6 C7 C8 N1 178.3(5) . . . . ? C6 C7 C8 C3 -0.4(6) . . . . ? N1 C1 C9 C14 -56.7(5) . . . . ? C2 C1 C9 C14 63.5(5) . . . . ? N1 C1 C9 C10 121.8(4) . . . . ? C2 C1 C9 C10 -118.0(4) . . . . ? C14 C9 C10 C11 -1.4(6) . . . . ? C1 C9 C10 C11 -180.0(4) . . . . ? C14 C9 C10 Cl1 176.7(3) . . . . ? C1 C9 C10 Cl1 -1.9(5) . . . . ? C9 C10 C11 C12 0.9(8) . . . . ? Cl1 C10 C11 C12 -177.2(4) . . . . ? C10 C11 C12 C13 0.7(8) . . . . ? C11 C12 C13 C14 -1.8(8) . . . . ? C12 C13 C14 C9 1.3(8) . . . . ? C10 C9 C14 C13 0.3(6) . . . . ? C1 C9 C14 C13 178.9(4) . . . . ? O1 C2 C15 O3 -3.5(5) . . . . ? C1 C2 C15 O3 -126.2(4) . . . . ? C18 C2 C15 O3 113.9(5) . . . . ? O1 C2 C15 O2 177.6(3) . . . . ? C1 C2 C15 O2 55.0(4) . . . . ? C18 C2 C15 O2 -65.0(4) . . . . ? O1 C2 C18 O4 -142.9(4) . . . . ? C1 C2 C18 O4 -17.8(6) . . . . ? C15 C2 C18 O4 102.9(5) . . . . ? O1 C2 C18 O5 38.0(5) . . . . ? C1 C2 C18 O5 163.1(4) . . . . ? C15 C2 C18 O5 -76.2(4) . . . . ? C3 C8 N1 C1 1.6(6) . . . . ? C7 C8 N1 C1 -177.0(4) . . . . ? C9 C1 N1 C8 95.6(4) . . . . ? C2 C1 N1 C8 -27.5(5) . . . . ? C8 C3 O1 C2 26.0(5) . . . . ? C4 C3 O1 C2 -155.9(3) . . . . ? C1 C2 O1 C3 -53.9(4) . . . . ? C15 C2 O1 C3 -175.9(3) . . . . ? C18 C2 O1 C3 69.9(4) . . . . ? O3 C15 O2 C16 -1.9(7) . . . . ? C2 C15 O2 C16 176.9(4) . . . . ? C17 C16 O2 C15 82.1(7) . . . . ? O4 C18 O5 C19 3.6(8) . . . . ? C2 C18 O5 C19 -177.3(6) . . . . ? C20 C19 O5 C18 152.3(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.431 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.044 # Attachment '- 4ra CCDC 881884.CIF' data_4ra _database_code_depnum_ccdc_archive 'CCDC 881884' #TrackingRef '- 4ra CCDC 881884.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 N O5' _chemical_formula_sum 'C18 H15 N O5' _chemical_formula_weight 325.31 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 Cc 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' _cell_length_a 12.4785(4) _cell_length_b 13.3392(5) _cell_length_c 10.0137(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.019(2) _cell_angle_gamma 90.00 _cell_volume 1623.97(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2864 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .48 _exptl_crystal_size_mid .32 _exptl_crystal_size_min .28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min .96 _exptl_absorpt_correction_T_max .97 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEXII area-detector diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6854 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3230 _reflns_number_gt 2830 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEXII (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material SHELXTL _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^)+(0.0649P)^2^+0.2202P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0079(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(10) _refine_ls_number_reflns 3230 _refine_ls_number_parameters 218 _refine_ls_number_restraints 2 _refine_ls_R_factor_ref 0.0447 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C 0.70978(16) 0.04256(13) 0.1770(2) 0.0491(4) Uani 1 1 d . . . H1B H 0.6841 0.0066 0.0903 0.059 Uiso 1 1 calc R . . C2 C 0.68775(15) 0.15570(13) 0.1578(2) 0.0456(4) Uani 1 1 d . . . C3 C 0.50128(16) 0.11596(15) 0.1629(2) 0.0498(4) Uani 1 1 d . . . C4 C 0.39132(18) 0.14061(18) 0.1255(2) 0.0633(6) Uani 1 1 d . . . H4A H 0.3683 0.1959 0.0698 0.076 Uiso 1 1 calc R . . C5 C 0.3157(2) 0.0820(2) 0.1719(3) 0.0749(7) Uani 1 1 d . . . H5A H 0.2412 0.0975 0.1463 0.090 Uiso 1 1 calc R . . C6 C 0.3503(2) 0.0005(2) 0.2561(3) 0.0759(7) Uani 1 1 d . . . H6A H 0.2991 -0.0378 0.2883 0.091 Uiso 1 1 calc R . . C7 C 0.4596(2) -0.02395(18) 0.2923(3) 0.0649(6) Uani 1 1 d . . . H7A H 0.4821 -0.0787 0.3491 0.078 Uiso 1 1 calc R . . C8 C 0.53718(16) 0.03222(14) 0.24508(19) 0.0510(5) Uani 1 1 d . . . C9 C 0.83062(17) 0.02756(15) 0.2310(2) 0.0530(5) Uani 1 1 d . . . C10 C 0.8883(2) -0.0537(2) 0.1931(3) 0.0771(7) Uani 1 1 d . . . H10A H 0.8519 -0.1002 0.1296 0.092 Uiso 1 1 calc R . . C11 C 0.9983(3) -0.0645(3) 0.2495(4) 0.1028(12) Uani 1 1 d . . . H11A H 1.0365 -0.1183 0.2237 0.123 Uiso 1 1 calc R . . C12 C 1.0520(3) 0.0028(4) 0.3432(4) 0.1069(14) Uani 1 1 d . . . H12A H 1.1264 -0.0066 0.3817 0.128 Uiso 1 1 calc R . . C13 C 0.9982(2) 0.0855(2) 0.3827(3) 0.0782(7) Uani 1 1 d . . . H13A H 1.0355 0.1322 0.4452 0.094 Uiso 1 1 calc R . . C14 C 0.88729(15) 0.09517(17) 0.3251(2) 0.0546(5) Uani 1 1 d . . . C15 C 0.73387(15) 0.20747(14) 0.2964(2) 0.0492(4) Uani 1 1 d . . . C16 C 0.74135(17) 0.19721(13) 0.0457(2) 0.0496(4) Uani 1 1 d . . . C17 C 0.8994(4) 0.2859(4) 0.0052(4) 0.1239(15) Uani 1 1 d . . . H17A H 0.8769 0.2541 -0.0838 0.149 Uiso 1 1 calc R . . H17B H 0.8908 0.3578 -0.0073 0.149 Uiso 1 1 calc R . . C18 C 1.0117(4) 0.2625(4) 0.0643(6) 0.1419(18) Uani 1 1 d . . . H18A H 1.0571 0.2862 0.0052 0.213 Uiso 1 1 calc R . . H18B H 1.0199 0.1913 0.0754 0.213 Uiso 1 1 calc R . . H18C H 1.0336 0.2945 0.1522 0.213 Uiso 1 1 calc R . . N1 N 0.64947(14) 0.01088(13) 0.27794(19) 0.0554(4) Uani 1 1 d . . . H1A H 0.6808 -0.0189 0.3527 0.067 Uiso 1 1 calc R . . O1 O 0.57421(11) 0.17669(10) 0.11289(16) 0.0578(4) Uani 1 1 d . . . O2 O 0.83291(11) 0.17642(11) 0.36928(14) 0.0572(4) Uani 1 1 d . . . O3 O 0.68822(14) 0.27264(12) 0.34193(18) 0.0706(5) Uani 1 1 d . . . O4 O 0.70660(18) 0.18155(14) -0.07284(17) 0.0808(6) Uani 1 1 d . . . O5 O 0.82938(16) 0.24948(16) 0.09746(17) 0.0863(6) Uani 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 C1 0.0604(11) 0.0394(8) 0.0444(10) 0.0023(8) 0.0056(9) 0.0065(8) C2 0.0444(9) 0.0419(8) 0.0465(10) 0.0031(8) 0.0019(8) 0.0054(6) C3 0.0497(9) 0.0521(9) 0.0437(10) 0.0029(8) 0.0022(8) 0.0002(8) C4 0.0542(11) 0.0676(12) 0.0621(13) 0.0020(11) 0.0007(10) 0.0066(9) C5 0.0508(11) 0.0877(17) 0.086(2) -0.0067(14) 0.0158(12) -0.0008(11) C6 0.0679(15) 0.0807(16) 0.0872(19) -0.0041(15) 0.0343(15) -0.0101(12) C7 0.0762(14) 0.0580(11) 0.0637(14) 0.0032(11) 0.0225(12) -0.0031(10) C8 0.0538(10) 0.0520(10) 0.0442(11) 0.0002(9) 0.0048(9) 0.0005(8) C9 0.0599(11) 0.0543(10) 0.0465(10) 0.0075(9) 0.0153(9) 0.0202(8) C10 0.1006(19) 0.0701(14) 0.0660(14) 0.0055(12) 0.0304(14) 0.0380(13) C11 0.105(2) 0.129(3) 0.081(2) 0.015(2) 0.035(2) 0.074(2) C12 0.0631(15) 0.172(4) 0.091(2) 0.042(3) 0.0293(17) 0.064(2) C13 0.0518(12) 0.115(2) 0.0654(15) 0.0074(15) 0.0084(11) 0.0142(13) C14 0.0468(10) 0.0736(13) 0.0442(10) 0.0050(10) 0.0118(9) 0.0182(9) C15 0.0469(10) 0.0496(9) 0.0511(11) -0.0001(9) 0.0108(8) 0.0088(8) C16 0.0646(11) 0.0382(8) 0.0437(10) 0.0010(8) 0.0071(9) 0.0008(7) C17 0.126(3) 0.175(4) 0.076(2) 0.020(2) 0.031(2) -0.068(3) C18 0.125(3) 0.182(5) 0.147(4) -0.027(3) 0.089(3) -0.023(3) N1 0.0567(9) 0.0520(8) 0.0546(10) 0.0171(8) 0.0062(8) 0.0074(7) O1 0.0467(7) 0.0544(7) 0.0657(9) 0.0188(7) -0.0012(7) 0.0039(6) O2 0.0512(7) 0.0692(8) 0.0473(8) -0.0102(7) 0.0032(6) 0.0096(6) O3 0.0715(10) 0.0669(9) 0.0740(11) -0.0161(8) 0.0174(8) 0.0187(8) O4 0.1161(15) 0.0783(10) 0.0446(9) -0.0081(8) 0.0111(9) -0.0296(10) O5 0.0901(13) 0.1205(15) 0.0472(9) 0.0024(9) 0.0130(9) -0.0492(11) _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 C1 N1 1.453(3) . ? C1 C9 1.496(3) . ? C1 C2 1.538(2) . ? C1 H1B 0.9800 . ? C2 O1 1.415(2) . ? C2 C16 1.534(3) . ? C2 C15 1.541(3) . ? C3 C4 1.378(3) . ? C3 O1 1.393(2) . ? C3 C8 1.400(3) . ? C4 C5 1.383(3) . ? C4 H4A 0.9300 . ? C5 C6 1.384(4) . ? C5 H5A 0.9300 . ? C6 C7 1.369(3) . ? C6 H6A 0.9300 . ? C7 C8 1.389(3) . ? C7 H7A 0.9300 . ? C8 N1 1.395(2) . ? C9 C14 1.379(3) . ? C9 C10 1.400(3) . ? C10 C11 1.369(5) . ? C10 H10A 0.9300 . ? C11 C12 1.361(6) . ? C11 H11A 0.9300 . ? C12 C13 1.395(5) . ? C12 H12A 0.9300 . ? C13 C14 1.381(3) . ? C13 H13A 0.9300 . ? C14 O2 1.402(2) . ? C15 O3 1.185(2) . ? C15 O2 1.351(2) . ? C16 O4 1.187(3) . ? C16 O5 1.306(3) . ? C17 C18 1.427(6) . ? C17 O5 1.489(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 H1A 0.8600 . ? 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 N1 C1 C9 110.33(15) . . ? N1 C1 C2 105.43(16) . . ? C9 C1 C2 108.27(15) . . ? N1 C1 H1B 110.9 . . ? C9 C1 H1B 110.9 . . ? C2 C1 H1B 110.9 . . ? O1 C2 C16 105.44(14) . . ? O1 C2 C1 111.83(15) . . ? C16 C2 C1 110.50(16) . . ? O1 C2 C15 110.00(16) . . ? C16 C2 C15 111.19(15) . . ? C1 C2 C15 107.91(15) . . ? C4 C3 O1 117.02(17) . . ? C4 C3 C8 121.17(19) . . ? O1 C3 C8 121.79(17) . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C4 C5 C6 120.4(2) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C7 C6 C5 120.2(2) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C6 C7 C8 120.7(2) . . ? C6 C7 H7A 119.6 . . ? C8 C7 H7A 119.6 . . ? C7 C8 N1 123.37(17) . . ? C7 C8 C3 118.36(18) . . ? N1 C8 C3 118.24(17) . . ? C14 C9 C10 118.4(2) . . ? C14 C9 C1 118.66(16) . . ? C10 C9 C1 122.9(2) . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C11 C12 C13 121.6(3) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C14 C13 C12 117.2(3) . . ? C14 C13 H13A 121.4 . . ? C12 C13 H13A 121.4 . . ? C9 C14 C13 122.4(2) . . ? C9 C14 O2 120.74(16) . . ? C13 C14 O2 116.8(2) . . ? O3 C15 O2 118.52(18) . . ? O3 C15 C2 124.11(17) . . ? O2 C15 C2 117.37(15) . . ? O4 C16 O5 125.2(2) . . ? O4 C16 C2 123.18(19) . . ? O5 C16 C2 111.65(17) . . ? C18 C17 O5 109.3(3) . . ? C18 C17 H17A 109.8 . . ? O5 C17 H17A 109.8 . . ? C18 C17 H17B 109.8 . . ? O5 C17 H17B 109.8 . . ? H17A C17 H17B 108.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 N1 C1 115.27(16) . . ? C8 N1 H1A 122.4 . . ? C1 N1 H1A 122.4 . . ? C3 O1 C2 117.32(14) . . ? C15 O2 C14 121.02(14) . . ? C16 O5 C17 119.1(2) . . ? 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 N1 C1 C2 O1 -59.2(2) . . . . ? C9 C1 C2 O1 -177.24(15) . . . . ? N1 C1 C2 C16 -176.29(15) . . . . ? C9 C1 C2 C16 65.64(19) . . . . ? N1 C1 C2 C15 61.96(19) . . . . ? C9 C1 C2 C15 -56.1(2) . . . . ? O1 C3 C4 C5 179.5(2) . . . . ? C8 C3 C4 C5 0.9(3) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C4 C5 C6 C7 -1.2(4) . . . . ? C5 C6 C7 C8 -0.1(4) . . . . ? C6 C7 C8 N1 -179.8(2) . . . . ? C6 C7 C8 C3 1.8(3) . . . . ? C4 C3 C8 C7 -2.2(3) . . . . ? O1 C3 C8 C7 179.26(18) . . . . ? C4 C3 C8 N1 179.3(2) . . . . ? O1 C3 C8 N1 0.8(3) . . . . ? N1 C1 C9 C14 -77.0(2) . . . . ? C2 C1 C9 C14 37.9(2) . . . . ? N1 C1 C9 C10 101.3(2) . . . . ? C2 C1 C9 C10 -143.8(2) . . . . ? C14 C9 C10 C11 0.2(4) . . . . ? C1 C9 C10 C11 -178.0(2) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? C10 C11 C12 C13 -1.3(5) . . . . ? C11 C12 C13 C14 1.4(5) . . . . ? C10 C9 C14 C13 0.0(3) . . . . ? C1 C9 C14 C13 178.3(2) . . . . ? C10 C9 C14 O2 -178.3(2) . . . . ? C1 C9 C14 O2 0.0(3) . . . . ? C12 C13 C14 C9 -0.8(4) . . . . ? C12 C13 C14 O2 177.6(2) . . . . ? O1 C2 C15 O3 -15.9(3) . . . . ? C16 C2 C15 O3 100.5(2) . . . . ? C1 C2 C15 O3 -138.2(2) . . . . ? O1 C2 C15 O2 164.50(16) . . . . ? C16 C2 C15 O2 -79.09(19) . . . . ? C1 C2 C15 O2 42.2(2) . . . . ? O1 C2 C16 O4 -47.7(2) . . . . ? C1 C2 C16 O4 73.3(2) . . . . ? C15 C2 C16 O4 -166.9(2) . . . . ? O1 C2 C16 O5 133.36(18) . . . . ? C1 C2 C16 O5 -105.6(2) . . . . ? C15 C2 C16 O5 14.2(2) . . . . ? C7 C8 N1 C1 152.43(18) . . . . ? C3 C8 N1 C1 -29.2(3) . . . . ? C9 C1 N1 C8 172.87(17) . . . . ? C2 C1 N1 C8 56.2(2) . . . . ? C4 C3 O1 C2 176.10(19) . . . . ? C8 C3 O1 C2 -5.3(3) . . . . ? C16 C2 O1 C3 155.43(16) . . . . ? C1 C2 O1 C3 35.3(2) . . . . ? C15 C2 O1 C3 -84.60(19) . . . . ? O3 C15 O2 C14 175.7(2) . . . . ? C2 C15 O2 C14 -4.7(3) . . . . ? C9 C14 O2 C15 -18.7(3) . . . . ? C13 C14 O2 C15 162.9(2) . . . . ? O4 C16 O5 C17 -5.8(4) . . . . ? C2 C16 O5 C17 173.1(3) . . . . ? C18 C17 O5 C16 -131.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.204 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.028 _publ_section_references ; Sheldrick G.M.(1996), SADABS, Absorption Correction Program, University of Goeltingen, German Siemens(1994), SAINT Software Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA Siemens(1996), SMART Software Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA Siemens(1994), SHELXTL^TM^ Version 5 Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA ;