Electronic Supplementary Material for CrystEngComm This journal is (c) The royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jubaraj Baruah' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 INDIA ; _publ_contact_author_email JUBA@IITG.ERNET.IN _publ_section_title ; Structural aspects and properties of salt and inclusion compounds of 8-Hydroxyquinoline based amides ; loop_ _publ_author_name J.Baruah A.Karmakar R.S.Sarma # Attachment 'qcha01.cif' data_cycloqh _database_code_depnum_ccdc_archive 'CCDC 622166' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H50 N4 O9' _chemical_formula_weight 658.78 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 12.2204(2) _cell_length_b 12.5113(2) _cell_length_c 13.5098(2) _cell_angle_alpha 69.9460(10) _cell_angle_beta 87.2100(10) _cell_angle_gamma 68.8960(10) _cell_volume 1803.58(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5629 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.05 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.088 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21315 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.32 _reflns_number_total 8106 _reflns_number_gt 5044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1067P)^2^+0.7304P] 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_number_reflns 8106 _refine_ls_number_parameters 472 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1046 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.2305 _refine_ls_wR_factor_gt 0.2015 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 C1 C 0.8229(3) 0.3394(3) 0.3954(3) 0.0726(8) Uani 1 1 d . . . H1 H 0.8071 0.3913 0.3251 0.087 Uiso 1 1 calc R . . C2 C 0.8386(3) 0.3862(3) 0.4717(3) 0.0794(9) Uani 1 1 d . . . H2 H 0.8335 0.4669 0.4523 0.095 Uiso 1 1 calc R . . C3 C 0.8615(3) 0.3118(3) 0.5740(3) 0.0752(9) Uani 1 1 d . . . H3 H 0.8721 0.3415 0.6257 0.090 Uiso 1 1 calc R . . C4 C 0.8697(2) 0.1896(3) 0.6032(2) 0.0608(7) Uani 1 1 d . . . C5 C 0.8533(2) 0.1496(2) 0.52040(19) 0.0515(6) Uani 1 1 d . . . C6 C 0.8921(3) 0.1076(3) 0.7082(2) 0.0745(9) Uani 1 1 d . . . H6 H 0.9022 0.1336 0.7627 0.089 Uiso 1 1 calc R . . C7 C 0.8993(3) -0.0082(4) 0.7304(2) 0.0767(9) Uani 1 1 d . . . H7 H 0.9141 -0.0612 0.8002 0.092 Uiso 1 1 calc R . . C8 C 0.8847(3) -0.0508(3) 0.64963(19) 0.0617(7) Uani 1 1 d . . . H8 H 0.8907 -0.1314 0.6666 0.074 Uiso 1 1 calc R . . C9 C 0.8446(2) -0.1252(2) 0.48741(18) 0.0498(6) Uani 1 1 d . . . H9A H 0.7823 -0.1346 0.5329 0.060 Uiso 1 1 calc R . . H9B H 0.9189 -0.1844 0.5259 0.060 Uiso 1 1 calc R . . C10 C 0.8267(2) -0.1510(2) 0.38957(18) 0.0493(6) Uani 1 1 d . . . C11 C 0.7852(3) -0.0771(3) 0.1968(2) 0.0699(8) Uani 1 1 d . . . H11 H 0.8399 -0.1599 0.2051 0.084 Uiso 1 1 calc R . . C12 C 0.8245(5) 0.0086(6) 0.1106(3) 0.137(2) Uani 1 1 d . . . H12A H 0.9047 -0.0032 0.1295 0.165 Uiso 1 1 calc R . . H12B H 0.7750 0.0919 0.1030 0.165 Uiso 1 1 calc R . . C13 C 0.8193(5) -0.0096(7) 0.0048(3) 0.150(2) Uani 1 1 d . . . H13A H 0.8401 0.0524 -0.0499 0.180 Uiso 1 1 calc R . . H13B H 0.8767 -0.0889 0.0095 0.180 Uiso 1 1 calc R . . C14 C 0.7065(5) -0.0023(4) -0.0240(3) 0.1090(15) Uani 1 1 d . . . H14A H 0.7089 -0.0215 -0.0880 0.131 Uiso 1 1 calc R . . H14B H 0.6506 0.0804 -0.0385 0.131 Uiso 1 1 calc R . . C15 C 0.6676(7) -0.0877(10) 0.0608(4) 0.224(5) Uani 1 1 d . . . H15A H 0.7174 -0.1709 0.0684 0.268 Uiso 1 1 calc R . . H15B H 0.5875 -0.0761 0.0417 0.268 Uiso 1 1 calc R . . C16 C 0.6724(5) -0.0693(8) 0.1667(4) 0.181(3) Uani 1 1 d . . . H16A H 0.6151 0.0103 0.1616 0.217 Uiso 1 1 calc R . . H16B H 0.6508 -0.1308 0.2212 0.217 Uiso 1 1 calc R . . C17 C 0.4352(3) 0.3700(3) -0.0793(2) 0.0651(7) Uani 1 1 d . . . H17 H 0.3602 0.3698 -0.0640 0.078 Uiso 1 1 calc R . . C18 C 0.4674(3) 0.3922(3) -0.1839(2) 0.0830(10) Uani 1 1 d . . . H18 H 0.4132 0.4058 -0.2370 0.100 Uiso 1 1 calc R . . C19 C 0.5744(4) 0.3943(3) -0.2087(2) 0.0822(10) Uani 1 1 d . . . H19 H 0.5936 0.4080 -0.2783 0.099 Uiso 1 1 calc R . . C20 C 0.6578(3) 0.3759(3) -0.1303(2) 0.0631(7) Uani 1 1 d . . . C21 C 0.6282(2) 0.3520(2) -0.02353(18) 0.0515(6) Uani 1 1 d . . . C22 C 0.8106(3) 0.3340(3) 0.0323(3) 0.0730(8) Uani 1 1 d . . . H22 H 0.8636 0.3192 0.0869 0.088 Uiso 1 1 calc R . . C23 C 0.8473(3) 0.3582(3) -0.0708(3) 0.0850(10) Uani 1 1 d . . . H23 H 0.9221 0.3601 -0.0839 0.102 Uiso 1 1 calc R . . C24 C 0.7709(4) 0.3787(3) -0.1501(3) 0.0831(10) Uani 1 1 d . . . H24 H 0.7935 0.3948 -0.2188 0.100 Uiso 1 1 calc R . . C25 C 0.3821(2) 0.3128(3) 0.12899(19) 0.0556(6) Uani 1 1 d . . . H25A H 0.3756 0.2474 0.1096 0.067 Uiso 1 1 calc R . . H25B H 0.3201 0.3884 0.0880 0.067 Uiso 1 1 calc R . . C26 C 0.3657(2) 0.2873(2) 0.24551(19) 0.0516(6) Uani 1 1 d . . . C27 C 0.4492(2) 0.2365(3) 0.42408(18) 0.0548(6) Uani 1 1 d . . . H27 H 0.3776 0.2191 0.4442 0.066 Uiso 1 1 calc R . . C28 C 0.4425(3) 0.3449(3) 0.4526(2) 0.0675(8) Uani 1 1 d . . . H28A H 0.3726 0.4143 0.4159 0.081 Uiso 1 1 calc R . . H28B H 0.5105 0.3666 0.4293 0.081 Uiso 1 1 calc R . . C29 C 0.4387(3) 0.3182(3) 0.5714(2) 0.0758(9) Uani 1 1 d . . . H29A H 0.4411 0.3873 0.5873 0.091 Uiso 1 1 calc R . . H29B H 0.3652 0.3078 0.5930 0.091 Uiso 1 1 calc R . . C30 C 0.5408(3) 0.2041(4) 0.6337(2) 0.0796(10) Uani 1 1 d . . . H30A H 0.6139 0.2185 0.6197 0.095 Uiso 1 1 calc R . . H30B H 0.5317 0.1857 0.7087 0.095 Uiso 1 1 calc R . . C31 C 0.5466(3) 0.0972(3) 0.6042(2) 0.0764(9) Uani 1 1 d . . . H31A H 0.4771 0.0775 0.6250 0.092 Uiso 1 1 calc R . . H31B H 0.6150 0.0267 0.6420 0.092 Uiso 1 1 calc R . . C32 C 0.5541(3) 0.1249(3) 0.4854(2) 0.0655(7) Uani 1 1 d . . . H32A H 0.6262 0.1393 0.4652 0.079 Uiso 1 1 calc R . . H32B H 0.5560 0.0551 0.4683 0.079 Uiso 1 1 calc R . . C33 C 0.8616(2) 0.0262(2) 0.54653(18) 0.0486(6) Uani 1 1 d . . . C34 C 0.5145(2) 0.3486(2) -0.00058(17) 0.0510(6) Uani 1 1 d . . . H1N H 0.520(3) 0.262(3) 0.284(3) 0.082(10) Uiso 1 1 d . . . H5N H 0.781(2) 0.004(3) 0.295(2) 0.051(8) Uiso 1 1 d . . . H1O H 0.699(3) 0.252(3) 0.206(3) 0.078(10) Uiso 1 1 d . . . H2O H 0.751(3) 0.210(3) 0.312(3) 0.080(10) Uiso 1 1 d . . . H3O H 0.089(6) 0.381(6) 0.044(6) 0.21(3) Uiso 1 1 d . . . H4O H 0.136(5) 0.321(5) 0.158(4) 0.133(18) Uiso 1 1 d . . . H5O H 0.168(4) 0.389(4) 0.353(3) 0.106(15) Uiso 1 1 d . . . H6O H 0.130(3) 0.388(3) 0.449(3) 0.088(12) Uiso 1 1 d . . . H7O H 0.984(4) 0.543(4) 0.306(4) 0.119(16) Uiso 1 1 d . . . H8O H 0.892(5) 0.645(5) 0.309(4) 0.15(2) Uiso 1 1 d . . . H9O H 0.111(5) 0.427(5) 0.857(4) 0.133(19) Uiso 1 1 d . . . H10O H 0.042(7) 0.514(6) 0.891(5) 0.19(3) Uiso 1 1 d . . . N1 N 0.8291(2) 0.2256(2) 0.41731(17) 0.0582(5) Uani 1 1 d . . . N2 N 0.7938(2) -0.0600(2) 0.29799(17) 0.0587(6) Uani 1 1 d . . . N3 N 0.7058(2) 0.3311(2) 0.05594(17) 0.0579(6) Uani 1 1 d . . . N4 N 0.4555(2) 0.2617(2) 0.31030(16) 0.0563(6) Uani 1 1 d . . . O1 O 0.84484(15) -0.00587(15) 0.46268(12) 0.0508(4) Uani 1 1 d . . . O2 O 0.84504(18) -0.25880(17) 0.40095(14) 0.0614(5) Uani 1 1 d . . . O3 O 0.49254(15) 0.32254(18) 0.10399(12) 0.0563(5) Uani 1 1 d . . . O4 O 0.26615(16) 0.2908(2) 0.27313(14) 0.0668(5) Uani 1 1 d . . . O5 O 0.69977(17) 0.19883(18) 0.26796(15) 0.0578(5) Uani 1 1 d . . . O6 O 0.0792(3) 0.3343(3) 0.1195(3) 0.0952(8) Uani 1 1 d . . . O7 O 0.1258(2) 0.4298(2) 0.3887(2) 0.0792(7) Uani 1 1 d . . . O8 O 0.9231(4) 0.6015(3) 0.2686(2) 0.1174(12) Uani 1 1 d . . . O9 O 0.1218(3) 0.4468(3) 0.9068(2) 0.0990(9) 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 0.0738(19) 0.0606(18) 0.084(2) -0.0252(16) 0.0014(16) -0.0240(15) C2 0.079(2) 0.0652(19) 0.107(3) -0.0431(19) 0.0081(19) -0.0279(17) C3 0.0694(19) 0.089(2) 0.095(2) -0.061(2) 0.0181(17) -0.0342(17) C4 0.0519(15) 0.081(2) 0.0665(16) -0.0433(15) 0.0121(12) -0.0278(14) C5 0.0423(12) 0.0656(16) 0.0533(13) -0.0285(12) 0.0074(10) -0.0205(11) C6 0.082(2) 0.104(3) 0.0587(17) -0.0477(17) 0.0110(14) -0.0406(19) C7 0.088(2) 0.102(3) 0.0449(14) -0.0281(15) 0.0051(14) -0.039(2) C8 0.0702(17) 0.0717(18) 0.0447(13) -0.0206(12) 0.0061(12) -0.0276(14) C9 0.0564(14) 0.0507(14) 0.0438(12) -0.0163(10) 0.0084(10) -0.0219(11) C10 0.0508(13) 0.0524(14) 0.0458(12) -0.0184(11) 0.0081(10) -0.0193(11) C11 0.105(2) 0.0492(15) 0.0505(14) -0.0160(12) -0.0134(15) -0.0220(15) C12 0.163(4) 0.253(7) 0.064(2) -0.072(3) 0.040(2) -0.140(5) C13 0.148(4) 0.278(8) 0.074(3) -0.093(4) 0.036(3) -0.109(5) C14 0.147(4) 0.106(3) 0.0541(19) -0.0264(19) -0.020(2) -0.021(3) C15 0.240(8) 0.473(14) 0.086(3) -0.116(6) 0.038(4) -0.260(10) C16 0.130(4) 0.399(11) 0.086(3) -0.109(5) 0.037(3) -0.161(6) C17 0.0664(17) 0.0778(19) 0.0459(13) -0.0239(13) 0.0006(12) -0.0179(14) C18 0.101(3) 0.103(3) 0.0381(14) -0.0249(15) -0.0029(15) -0.029(2) C19 0.116(3) 0.096(2) 0.0375(14) -0.0222(14) 0.0176(16) -0.044(2) C20 0.090(2) 0.0535(15) 0.0458(13) -0.0179(11) 0.0216(13) -0.0277(14) C21 0.0677(16) 0.0441(13) 0.0428(12) -0.0145(10) 0.0102(11) -0.0219(12) C22 0.0697(19) 0.080(2) 0.079(2) -0.0288(16) 0.0178(15) -0.0400(16) C23 0.087(2) 0.091(2) 0.094(2) -0.036(2) 0.041(2) -0.052(2) C24 0.113(3) 0.083(2) 0.0682(19) -0.0326(17) 0.047(2) -0.052(2) C25 0.0500(14) 0.0759(18) 0.0450(12) -0.0273(12) 0.0054(10) -0.0221(13) C26 0.0507(14) 0.0628(15) 0.0455(12) -0.0248(11) 0.0059(10) -0.0200(12) C27 0.0500(13) 0.0824(19) 0.0405(12) -0.0256(12) 0.0103(10) -0.0306(13) C28 0.0777(19) 0.0752(19) 0.0520(15) -0.0251(14) 0.0061(13) -0.0281(16) C29 0.093(2) 0.092(2) 0.0541(16) -0.0382(16) 0.0089(15) -0.0357(19) C30 0.073(2) 0.123(3) 0.0502(15) -0.0320(17) 0.0037(14) -0.042(2) C31 0.075(2) 0.092(2) 0.0470(15) -0.0153(15) 0.0065(13) -0.0221(17) C32 0.0654(17) 0.0743(19) 0.0524(15) -0.0209(13) 0.0108(12) -0.0226(15) C33 0.0450(12) 0.0617(15) 0.0443(12) -0.0249(11) 0.0063(9) -0.0198(11) C34 0.0612(15) 0.0521(14) 0.0354(11) -0.0163(10) 0.0062(10) -0.0150(11) N4 0.0499(12) 0.0844(16) 0.0424(11) -0.0266(10) 0.0105(9) -0.0299(12) N3 0.0646(14) 0.0624(13) 0.0512(12) -0.0190(10) 0.0104(10) -0.0299(11) N1 0.0604(13) 0.0553(13) 0.0600(13) -0.0204(10) 0.0010(10) -0.0217(11) N2 0.0797(16) 0.0493(14) 0.0481(12) -0.0195(11) 0.0020(10) -0.0221(12) O1 0.0626(10) 0.0510(9) 0.0422(8) -0.0179(7) 0.0040(7) -0.0232(8) O2 0.0806(13) 0.0519(11) 0.0526(10) -0.0205(8) 0.0033(9) -0.0227(9) O3 0.0531(10) 0.0828(13) 0.0360(8) -0.0228(8) 0.0073(7) -0.0268(9) O4 0.0483(10) 0.1040(16) 0.0533(10) -0.0329(10) 0.0104(8) -0.0293(10) O5 0.0623(11) 0.0701(12) 0.0410(9) -0.0151(9) 0.0035(8) -0.0280(9) O6 0.0850(18) 0.114(2) 0.0871(19) -0.0334(16) -0.0131(14) -0.0354(16) O7 0.0960(17) 0.0637(14) 0.0630(14) -0.0181(12) 0.0120(13) -0.0169(12) O8 0.166(3) 0.0766(17) 0.0683(15) -0.0349(14) -0.0252(17) 0.0162(19) O9 0.0863(19) 0.127(2) 0.0945(19) -0.0589(18) -0.0024(14) -0.0302(17) _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 1.325(4) . ? C1 C2 1.398(5) . ? C1 H1 0.9300 . ? C2 C3 1.351(5) . ? C2 H2 0.9300 . ? C3 C4 1.409(4) . ? C3 H3 0.9300 . ? C4 C6 1.405(4) . ? C4 C5 1.421(4) . ? C5 N1 1.364(3) . ? C5 C33 1.427(4) . ? C6 C7 1.345(5) . ? C6 H6 0.9300 . ? C7 C8 1.411(4) . ? C7 H7 0.9300 . ? C8 C33 1.367(3) . ? C8 H8 0.9300 . ? C9 O1 1.415(3) . ? C9 C10 1.507(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O2 1.240(3) . ? C10 N2 1.319(3) . ? C11 C16 1.417(5) . ? C11 N2 1.468(3) . ? C11 C12 1.482(5) . ? C11 H11 0.9800 . ? C12 C13 1.530(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.413(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.468(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.532(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C34 1.364(4) . ? C17 C18 1.408(4) . ? C17 H17 0.9300 . ? C18 C19 1.341(5) . ? C18 H18 0.9300 . ? C19 C20 1.408(5) . ? C19 H19 0.9300 . ? C20 C24 1.406(5) . ? C20 C21 1.426(3) . ? C21 N3 1.360(3) . ? C21 C34 1.421(4) . ? C22 N3 1.315(4) . ? C22 C23 1.406(5) . ? C22 H22 0.9300 . ? C23 C24 1.350(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 O3 1.413(3) . ? C25 C26 1.514(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 O4 1.245(3) . ? C26 N4 1.311(3) . ? C27 N4 1.464(3) . ? C27 C28 1.507(4) . ? C27 C32 1.517(4) . ? C27 H27 0.9800 . ? C28 C29 1.525(4) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.516(5) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.498(5) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.526(4) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 O1 1.371(3) . ? C34 O3 1.373(3) . ? N4 H4N 0.85(4) . ? N2 H2N 0.75(3) . ? O5 H1O 0.87(3) . ? O5 H2O 0.95(4) . ? O6 H3O 1.02(7) . ? O6 H4O 0.82(5) . ? O7 H5O 0.84(5) . ? O7 H6O 0.80(4) . ? O8 H7O 0.86(5) . ? O8 H8O 0.88(6) . ? O9 H9O 0.83(5) . ? O9 H10O 1.00(8) . ? 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 C2 123.9(3) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C3 C2 C1 118.6(3) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C6 C4 C3 123.7(3) . . ? C6 C4 C5 119.5(3) . . ? C3 C4 C5 116.9(3) . . ? N1 C5 C4 122.1(2) . . ? N1 C5 C33 119.3(2) . . ? C4 C5 C33 118.7(2) . . ? C7 C6 C4 120.5(3) . . ? C7 C6 H6 119.8 . . ? C4 C6 H6 119.8 . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C33 C8 C7 120.2(3) . . ? C33 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? O1 C9 C10 111.88(18) . . ? O1 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? O1 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O2 C10 N2 123.9(2) . . ? O2 C10 C9 116.8(2) . . ? N2 C10 C9 119.4(2) . . ? C16 C11 N2 114.4(3) . . ? C16 C11 C12 110.0(4) . . ? N2 C11 C12 111.3(3) . . ? C16 C11 H11 106.9 . . ? N2 C11 H11 106.9 . . ? C12 C11 H11 106.9 . . ? C11 C12 C13 112.3(4) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 112.2(4) . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 110.8(4) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 111.9(6) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C11 C16 C15 112.6(4) . . ? C11 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C11 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C34 C17 C18 119.7(3) . . ? C34 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 121.6(3) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C20 120.6(3) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C24 C20 C19 124.1(3) . . ? C24 C20 C21 116.8(3) . . ? C19 C20 C21 119.1(3) . . ? N3 C21 C34 119.8(2) . . ? N3 C21 C20 121.9(2) . . ? C34 C21 C20 118.4(2) . . ? N3 C22 C23 123.9(3) . . ? N3 C22 H22 118.1 . . ? C23 C22 H22 118.1 . . ? C24 C23 C22 118.2(3) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C23 C24 C20 120.9(3) . . ? C23 C24 H24 119.6 . . ? C20 C24 H24 119.6 . . ? O3 C25 C26 111.84(19) . . ? O3 C25 H25A 109.2 . . ? C26 C25 H25A 109.2 . . ? O3 C25 H25B 109.2 . . ? C26 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? O4 C26 N4 124.5(2) . . ? O4 C26 C25 116.4(2) . . ? N4 C26 C25 119.1(2) . . ? N4 C27 C28 111.5(2) . . ? N4 C27 C32 110.5(2) . . ? C28 C27 C32 110.2(2) . . ? N4 C27 H27 108.2 . . ? C28 C27 H27 108.2 . . ? C32 C27 H27 108.2 . . ? C27 C28 C29 111.7(2) . . ? C27 C28 H28A 109.3 . . ? C29 C28 H28A 109.3 . . ? C27 C28 H28B 109.3 . . ? C29 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? C30 C29 C28 111.7(3) . . ? C30 C29 H29A 109.3 . . ? C28 C29 H29A 109.3 . . ? C30 C29 H29B 109.3 . . ? C28 C29 H29B 109.3 . . ? H29A C29 H29B 107.9 . . ? C31 C30 C29 111.0(3) . . ? C31 C30 H30A 109.4 . . ? C29 C30 H30A 109.4 . . ? C31 C30 H30B 109.4 . . ? C29 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C30 C31 C32 111.2(3) . . ? C30 C31 H31A 109.4 . . ? C32 C31 H31A 109.4 . . ? C30 C31 H31B 109.4 . . ? C32 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? C27 C32 C31 110.5(2) . . ? C27 C32 H32A 109.5 . . ? C31 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C8 C33 O1 124.7(2) . . ? C8 C33 C5 119.9(2) . . ? O1 C33 C5 115.4(2) . . ? C17 C34 O3 124.0(2) . . ? C17 C34 C21 120.6(2) . . ? O3 C34 C21 115.4(2) . . ? C26 N4 C27 123.6(2) . . ? C26 N4 H4N 117(2) . . ? C27 N4 H4N 119(2) . . ? C22 N3 C21 118.3(2) . . ? C1 N1 C5 117.8(2) . . ? C10 N2 C11 123.5(2) . . ? C10 N2 H2N 120(2) . . ? C11 N2 H2N 116(2) . . ? C33 O1 C9 116.39(18) . . ? C34 O3 C25 116.16(18) . . ? H1O O5 H2O 103(3) . . ? H3O O6 H4O 109(5) . . ? H5O O7 H6O 111(4) . . ? H7O O8 H8O 104(4) . . ? H9O O9 H10O 92(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 C3 0.0(5) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 C6 -179.4(3) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C6 C4 C5 N1 178.8(2) . . . . ? C3 C4 C5 N1 -0.9(4) . . . . ? C6 C4 C5 C33 -0.8(4) . . . . ? C3 C4 C5 C33 179.5(2) . . . . ? C3 C4 C6 C7 -179.7(3) . . . . ? C5 C4 C6 C7 0.6(4) . . . . ? C4 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C33 -0.7(5) . . . . ? O1 C9 C10 O2 168.0(2) . . . . ? O1 C9 C10 N2 -11.5(3) . . . . ? C16 C11 C12 C13 -53.5(6) . . . . ? N2 C11 C12 C13 178.6(4) . . . . ? C11 C12 C13 C14 54.6(7) . . . . ? C12 C13 C14 C15 -54.1(7) . . . . ? C13 C14 C15 C16 54.1(8) . . . . ? N2 C11 C16 C15 -180.0(6) . . . . ? C12 C11 C16 C15 53.8(8) . . . . ? C14 C15 C16 C11 -55.2(9) . . . . ? C34 C17 C18 C19 -0.7(5) . . . . ? C17 C18 C19 C20 -1.0(6) . . . . ? C18 C19 C20 C24 -178.9(3) . . . . ? C18 C19 C20 C21 1.5(5) . . . . ? C24 C20 C21 N3 -0.9(4) . . . . ? C19 C20 C21 N3 178.7(3) . . . . ? C24 C20 C21 C34 179.9(3) . . . . ? C19 C20 C21 C34 -0.5(4) . . . . ? N3 C22 C23 C24 -0.6(5) . . . . ? C22 C23 C24 C20 0.0(5) . . . . ? C19 C20 C24 C23 -178.9(3) . . . . ? C21 C20 C24 C23 0.7(5) . . . . ? O3 C25 C26 O4 172.3(2) . . . . ? O3 C25 C26 N4 -8.7(4) . . . . ? N4 C27 C28 C29 -178.7(2) . . . . ? C32 C27 C28 C29 -55.7(3) . . . . ? C27 C28 C29 C30 54.2(4) . . . . ? C28 C29 C30 C31 -53.9(4) . . . . ? C29 C30 C31 C32 55.9(4) . . . . ? N4 C27 C32 C31 -179.0(2) . . . . ? C28 C27 C32 C31 57.3(3) . . . . ? C30 C31 C32 C27 -58.0(4) . . . . ? C7 C8 C33 O1 -179.3(2) . . . . ? C7 C8 C33 C5 0.5(4) . . . . ? N1 C5 C33 C8 -179.4(2) . . . . ? C4 C5 C33 C8 0.2(3) . . . . ? N1 C5 C33 O1 0.4(3) . . . . ? C4 C5 C33 O1 180.0(2) . . . . ? C18 C17 C34 O3 -178.0(3) . . . . ? C18 C17 C34 C21 1.8(4) . . . . ? N3 C21 C34 C17 179.6(3) . . . . ? C20 C21 C34 C17 -1.2(4) . . . . ? N3 C21 C34 O3 -0.6(4) . . . . ? C20 C21 C34 O3 178.7(2) . . . . ? O4 C26 N4 C27 -1.6(4) . . . . ? C25 C26 N4 C27 179.5(2) . . . . ? C28 C27 N4 C26 -102.8(3) . . . . ? C32 C27 N4 C26 134.3(3) . . . . ? C23 C22 N3 C21 0.4(5) . . . . ? C34 C21 N3 C22 179.5(3) . . . . ? C20 C21 N3 C22 0.3(4) . . . . ? C2 C1 N1 C5 -0.5(4) . . . . ? C4 C5 N1 C1 1.0(4) . . . . ? C33 C5 N1 C1 -179.4(2) . . . . ? O2 C10 N2 C11 -5.7(4) . . . . ? C9 C10 N2 C11 173.8(3) . . . . ? C16 C11 N2 C10 92.2(5) . . . . ? C12 C11 N2 C10 -142.3(4) . . . . ? C8 C33 O1 C9 4.0(3) . . . . ? C5 C33 O1 C9 -175.8(2) . . . . ? C10 C9 O1 C33 -179.45(19) . . . . ? C17 C34 O3 C25 2.8(4) . . . . ? C21 C34 O3 C25 -177.0(2) . . . . ? C26 C25 O3 C34 -178.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 0.731 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.045 # Attachment 'qdmano3.cif' data_dmano3 _database_code_depnum_ccdc_archive 'CCDC 622167' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H38 N6 O10' _chemical_formula_weight 738.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 P2(1)/c 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 20.7294(19) _cell_length_b 7.8139(7) _cell_length_c 22.774(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.081(2) _cell_angle_gamma 90.00 _cell_volume 3578.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2434 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 21.05 _exptl_crystal_description rods _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.101 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25241 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.25 _reflns_number_total 8478 _reflns_number_gt 3963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0637P)^2^+3.2068P] 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_number_reflns 8478 _refine_ls_number_parameters 507 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1887 _refine_ls_R_factor_gt 0.0958 _refine_ls_wR_factor_ref 0.2165 _refine_ls_wR_factor_gt 0.1779 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.34770(18) 0.3780(5) 0.35129(17) 0.0471(9) Uani 1 1 d . . . C2 C 0.3107(2) 0.3203(6) 0.3891(2) 0.0652(12) Uani 1 1 d . . . H2 H 0.3315 0.2965 0.4292 0.078 Uiso 1 1 calc R . . C3 C 0.2419(2) 0.2962(6) 0.3686(2) 0.0715(13) Uani 1 1 d . . . H3 H 0.2179 0.2569 0.3954 0.086 Uiso 1 1 calc R . . C4 C 0.2098(2) 0.3291(6) 0.3104(2) 0.0670(12) Uani 1 1 d . . . H4 H 0.1640 0.3139 0.2977 0.080 Uiso 1 1 calc R . . C5 C 0.24588(18) 0.3860(5) 0.26949(18) 0.0522(10) Uani 1 1 d . . . C6 C 0.31522(17) 0.4112(5) 0.29013(17) 0.0450(9) Uani 1 1 d . . . C7 C 0.2171(2) 0.4186(6) 0.2074(2) 0.0711(13) Uani 1 1 d . . . H7 H 0.1716 0.4043 0.1922 0.085 Uiso 1 1 calc R . . C8 C 0.2547(2) 0.4700(7) 0.1702(2) 0.0760(14) Uani 1 1 d . . . H8 H 0.2352 0.4907 0.1295 0.091 Uiso 1 1 calc R . . C9 C 0.3227(2) 0.4921(6) 0.19265(19) 0.0678(12) Uani 1 1 d . . . H9 H 0.3489 0.5259 0.1668 0.081 Uiso 1 1 calc R . . C10 C 0.45215(18) 0.3347(5) 0.41995(18) 0.0589(11) Uani 1 1 d . . . H10A H 0.4541 0.2121 0.4138 0.071 Uiso 1 1 calc R . . H10B H 0.4295 0.3537 0.4520 0.071 Uiso 1 1 calc R . . C11 C 0.52191(18) 0.4027(5) 0.44006(18) 0.0486(9) Uani 1 1 d . . . C12 C 0.60805(17) 0.5946(5) 0.42493(16) 0.0477(9) Uani 1 1 d . . . C13 C 0.66485(19) 0.4939(5) 0.43106(18) 0.0533(10) Uani 1 1 d . . . C14 C 0.72636(19) 0.5687(6) 0.45383(18) 0.0609(12) Uani 1 1 d . . . H14 H 0.7646 0.5023 0.4596 0.073 Uiso 1 1 calc R . . C15 C 0.7315(2) 0.7401(6) 0.46800(18) 0.0601(11) Uani 1 1 d . . . H15 H 0.7732 0.7892 0.4831 0.072 Uiso 1 1 calc R . . C16 C 0.6755(2) 0.8380(6) 0.45992(19) 0.0605(11) Uani 1 1 d . . . H16 H 0.6796 0.9542 0.4690 0.073 Uiso 1 1 calc R . . C17 C 0.61244(18) 0.7690(5) 0.43857(18) 0.0507(10) Uani 1 1 d . . . C18 C 0.6597(2) 0.3080(6) 0.4128(2) 0.0798(14) Uani 1 1 d . . . H18A H 0.6442 0.2425 0.4423 0.120 Uiso 1 1 calc R . . H18B H 0.7027 0.2670 0.4105 0.120 Uiso 1 1 calc R . . H18C H 0.6290 0.2962 0.3740 0.120 Uiso 1 1 calc R . . C19 C 0.5513(2) 0.8781(5) 0.4314(2) 0.0750(14) Uani 1 1 d . . . H19A H 0.5639 0.9906 0.4469 0.112 Uiso 1 1 calc R . . H19B H 0.5221 0.8276 0.4534 0.112 Uiso 1 1 calc R . . H19C H 0.5290 0.8856 0.3893 0.112 Uiso 1 1 calc R . . C20 C 0.18006(17) 0.8737(5) 0.27170(17) 0.0472(9) Uani 1 1 d . . . C21 C 0.17298(19) 0.9329(6) 0.21463(18) 0.0606(11) Uani 1 1 d . . . H21 H 0.1307 0.9447 0.1892 0.073 Uiso 1 1 calc R . . C22 C 0.2296(2) 0.9768(6) 0.19360(19) 0.0665(12) Uani 1 1 d . . . H22 H 0.2238 1.0173 0.1543 0.080 Uiso 1 1 calc R . . C23 C 0.2918(2) 0.9617(5) 0.22904(19) 0.0588(11) Uani 1 1 d . . . H23 H 0.3282 0.9911 0.2140 0.071 Uiso 1 1 calc R . . C24 C 0.30143(18) 0.9011(5) 0.28888(18) 0.0486(9) Uani 1 1 d . . . C25 C 0.24517(17) 0.8571(4) 0.31004(16) 0.0426(9) Uani 1 1 d . . . C26 C 0.36451(18) 0.8802(5) 0.3292(2) 0.0592(11) Uani 1 1 d . . . H26 H 0.4027 0.9094 0.3169 0.071 Uiso 1 1 calc R . . C27 C 0.3699(2) 0.8176(6) 0.3862(2) 0.0691(13) Uani 1 1 d . . . H27 H 0.4116 0.8021 0.4124 0.083 Uiso 1 1 calc R . . C28 C 0.31306(19) 0.7776(5) 0.40444(19) 0.0602(11) Uani 1 1 d . . . H28 H 0.3166 0.7356 0.4433 0.072 Uiso 1 1 calc R . . C29 C 0.06430(18) 0.8437(6) 0.26289(19) 0.0662(13) Uani 1 1 d . . . H29A H 0.0583 0.7782 0.2258 0.079 Uiso 1 1 calc R . . H29B H 0.0561 0.9632 0.2521 0.079 Uiso 1 1 calc R . . C30 C 0.01527(19) 0.7843(6) 0.29723(19) 0.0582(11) Uani 1 1 d . . . C31 C -0.00392(17) 0.6567(5) 0.38872(16) 0.0463(9) Uani 1 1 d . . . C32 C 0.00229(18) 0.4830(5) 0.40193(16) 0.0470(9) Uani 1 1 d . . . C33 C -0.0421(2) 0.4129(6) 0.43243(18) 0.0581(11) Uani 1 1 d . . . H33 H -0.0400 0.2965 0.4413 0.070 Uiso 1 1 calc R . . C34 C -0.0888(2) 0.5122(7) 0.4496(2) 0.0670(12) Uani 1 1 d . . . H34 H -0.1187 0.4623 0.4690 0.080 Uiso 1 1 calc R . . C35 C -0.0917(2) 0.6837(6) 0.4383(2) 0.0647(12) Uani 1 1 d . . . H35 H -0.1229 0.7499 0.4511 0.078 Uiso 1 1 calc R . . C36 C -0.04909(18) 0.7614(5) 0.40837(18) 0.0546(10) Uani 1 1 d . . . C37 C -0.0486(2) 0.9525(6) 0.4013(3) 0.0859(16) Uani 1 1 d . . . H37A H -0.0591 0.9811 0.3590 0.129 Uiso 1 1 calc R . . H37B H -0.0053 0.9960 0.4204 0.129 Uiso 1 1 calc R . . H37C H -0.0810 1.0026 0.4198 0.129 Uiso 1 1 calc R . . C38 C 0.0562(2) 0.3781(6) 0.3860(2) 0.0679(12) Uani 1 1 d . . . H38A H 0.0527 0.3859 0.3433 0.102 Uiso 1 1 calc R . . H38B H 0.0516 0.2608 0.3968 0.102 Uiso 1 1 calc R . . H38C H 0.0988 0.4204 0.4077 0.102 Uiso 1 1 calc R . . H1N H 0.3929(19) 0.489(5) 0.2632(17) 0.056(12) Uiso 1 1 d . . . H2N H 0.517(2) 0.544(5) 0.3667(19) 0.069(13) Uiso 1 1 d . . . H3N H 0.2181(17) 0.784(4) 0.3825(14) 0.036(10) Uiso 1 1 d . . . H4N H 0.077(2) 0.736(5) 0.3672(17) 0.056(13) Uiso 1 1 d . . . N1 N 0.35034(17) 0.4654(4) 0.25028(15) 0.0513(9) Uani 1 1 d . . . N2 N 0.54310(15) 0.5182(4) 0.40547(15) 0.0513(8) Uani 1 1 d . . . N3 N 0.25387(15) 0.7978(4) 0.36777(15) 0.0493(8) Uani 1 1 d . . . N4 N 0.03809(17) 0.7309(4) 0.35387(16) 0.0527(9) Uani 1 1 d . . . N5 N 0.5055(2) 0.6290(5) 0.2469(2) 0.0652(10) Uani 1 1 d . . . N6 N 0.16809(18) 0.8584(5) 0.4704(2) 0.0666(10) Uani 1 1 d . . . O1 O 0.41438(11) 0.4106(3) 0.36594(11) 0.0536(7) Uani 1 1 d . . . O2 O 0.55530(13) 0.3496(4) 0.48856(12) 0.0631(8) Uani 1 1 d . . . O3 O 0.13130(12) 0.8239(4) 0.29816(11) 0.0611(8) Uani 1 1 d . . . O4 O -0.04398(13) 0.7842(5) 0.27064(14) 0.0867(11) Uani 1 1 d . . . O5 O 0.47208(15) 0.6125(5) 0.28515(14) 0.0835(10) Uani 1 1 d . . . O6 O 0.4782(2) 0.6141(7) 0.19406(19) 0.1374(18) Uani 1 1 d . . . O7 O 0.56433(17) 0.6618(5) 0.26294(19) 0.1066(13) Uani 1 1 d . . . O8 O 0.17201(14) 0.7246(4) 0.44077(13) 0.0635(8) Uani 1 1 d . . . O9 O 0.1713(3) 0.8609(6) 0.5232(2) 0.1256(16) Uani 1 1 d . . . O10 O 0.1585(3) 0.9925(6) 0.4411(2) 0.152(2) 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 0.037(2) 0.058(2) 0.046(2) -0.0022(19) 0.0102(18) -0.0055(18) C2 0.045(2) 0.096(3) 0.053(3) 0.007(2) 0.009(2) -0.011(2) C3 0.046(3) 0.103(4) 0.069(3) 0.007(3) 0.021(2) -0.016(2) C4 0.037(2) 0.091(3) 0.071(3) -0.001(3) 0.010(2) -0.008(2) C5 0.035(2) 0.062(2) 0.057(3) -0.004(2) 0.0066(18) 0.0007(18) C6 0.039(2) 0.051(2) 0.047(2) 0.0003(18) 0.0128(18) 0.0003(17) C7 0.049(3) 0.090(3) 0.063(3) 0.005(3) -0.007(2) 0.000(2) C8 0.063(3) 0.106(4) 0.050(3) 0.015(3) -0.003(2) -0.005(3) C9 0.061(3) 0.092(3) 0.049(3) 0.014(2) 0.009(2) 0.003(2) C10 0.045(2) 0.068(3) 0.056(3) 0.014(2) -0.0027(19) -0.006(2) C11 0.038(2) 0.057(2) 0.048(2) 0.003(2) 0.0057(18) -0.0042(18) C12 0.036(2) 0.062(3) 0.043(2) 0.0066(19) 0.0058(16) -0.0052(18) C13 0.050(2) 0.061(3) 0.051(2) -0.002(2) 0.0184(19) 0.000(2) C14 0.035(2) 0.091(3) 0.060(3) 0.006(2) 0.0188(19) 0.003(2) C15 0.040(2) 0.080(3) 0.061(3) -0.002(2) 0.0124(19) -0.018(2) C16 0.050(3) 0.064(3) 0.069(3) 0.002(2) 0.016(2) -0.010(2) C17 0.037(2) 0.056(2) 0.059(3) 0.010(2) 0.0129(18) -0.0026(18) C18 0.079(3) 0.072(3) 0.095(4) -0.013(3) 0.032(3) 0.006(3) C19 0.050(3) 0.063(3) 0.110(4) 0.014(3) 0.015(3) 0.004(2) C20 0.033(2) 0.065(2) 0.045(2) 0.0029(19) 0.0122(17) -0.0048(18) C21 0.041(2) 0.091(3) 0.047(3) 0.013(2) 0.0045(19) -0.001(2) C22 0.058(3) 0.095(3) 0.050(3) 0.012(2) 0.018(2) -0.007(2) C23 0.048(2) 0.076(3) 0.059(3) 0.003(2) 0.026(2) -0.006(2) C24 0.039(2) 0.054(2) 0.055(3) 0.0007(19) 0.0164(18) 0.0020(18) C25 0.039(2) 0.048(2) 0.043(2) 0.0023(17) 0.0134(17) 0.0024(16) C26 0.033(2) 0.073(3) 0.075(3) 0.002(2) 0.018(2) -0.0011(19) C27 0.040(2) 0.090(3) 0.071(3) 0.012(3) 0.003(2) 0.002(2) C28 0.044(2) 0.077(3) 0.055(3) 0.014(2) 0.004(2) 0.004(2) C29 0.036(2) 0.103(3) 0.055(3) 0.026(2) 0.0013(19) -0.003(2) C30 0.038(2) 0.077(3) 0.057(3) 0.015(2) 0.006(2) -0.004(2) C31 0.0295(19) 0.064(3) 0.044(2) -0.0031(19) 0.0061(16) -0.0084(17) C32 0.043(2) 0.054(2) 0.041(2) -0.0035(18) 0.0050(17) -0.0054(18) C33 0.055(3) 0.062(3) 0.052(3) 0.005(2) 0.005(2) -0.014(2) C34 0.048(3) 0.095(4) 0.061(3) 0.007(3) 0.019(2) -0.017(3) C35 0.038(2) 0.091(4) 0.067(3) -0.010(3) 0.017(2) 0.000(2) C36 0.037(2) 0.064(3) 0.062(3) -0.008(2) 0.0107(19) -0.0028(19) C37 0.069(3) 0.064(3) 0.123(5) -0.012(3) 0.021(3) 0.004(2) C38 0.062(3) 0.068(3) 0.074(3) -0.007(2) 0.017(2) 0.008(2) N1 0.0369(19) 0.064(2) 0.051(2) 0.0053(16) 0.0072(16) 0.0008(16) N2 0.0383(18) 0.066(2) 0.046(2) 0.0088(17) 0.0033(15) -0.0091(16) N3 0.0312(18) 0.070(2) 0.048(2) 0.0048(16) 0.0124(16) 0.0001(16) N4 0.0301(18) 0.072(2) 0.055(2) 0.0088(18) 0.0086(16) -0.0055(17) N5 0.053(2) 0.076(3) 0.069(3) 0.007(2) 0.020(2) -0.0008(19) N6 0.070(3) 0.067(3) 0.059(3) 0.002(2) 0.009(2) -0.013(2) O1 0.0325(14) 0.0783(18) 0.0470(16) 0.0098(14) 0.0039(11) -0.0080(13) O2 0.0464(16) 0.081(2) 0.0545(18) 0.0232(15) -0.0015(13) -0.0071(14) O3 0.0304(14) 0.100(2) 0.0502(17) 0.0241(15) 0.0048(12) -0.0037(14) O4 0.0314(15) 0.151(3) 0.071(2) 0.035(2) -0.0003(14) -0.0089(18) O5 0.0531(19) 0.138(3) 0.060(2) 0.016(2) 0.0144(16) -0.0162(19) O6 0.129(4) 0.219(5) 0.064(3) -0.009(3) 0.024(3) -0.049(3) O7 0.054(2) 0.130(3) 0.142(3) 0.004(3) 0.036(2) -0.013(2) O8 0.0643(19) 0.0636(19) 0.066(2) 0.0004(16) 0.0232(15) -0.0052(15) O9 0.185(5) 0.121(3) 0.084(3) -0.016(3) 0.057(3) -0.012(3) O10 0.229(6) 0.080(3) 0.134(4) 0.003(3) 0.018(4) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.361(5) . ? C1 O1 1.365(4) . ? C1 C6 1.416(5) . ? C2 C3 1.401(5) . ? C2 H2 0.9300 . ? C3 C4 1.355(6) . ? C3 H3 0.9300 . ? C4 C5 1.402(6) . ? C4 H4 0.9300 . ? C5 C6 1.413(5) . ? C5 C7 1.418(6) . ? C6 N1 1.362(5) . ? C7 C8 1.345(6) . ? C7 H7 0.9300 . ? C8 C9 1.388(6) . ? C8 H8 0.9300 . ? C9 N1 1.315(5) . ? C9 H9 0.9300 . ? C10 O1 1.418(4) . ? C10 C11 1.504(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.225(4) . ? C11 N2 1.340(5) . ? C12 C13 1.395(5) . ? C12 C17 1.396(5) . ? C12 N2 1.441(4) . ? C13 C14 1.384(5) . ? C13 C18 1.507(6) . ? C14 C15 1.376(6) . ? C14 H14 0.9300 . ? C15 C16 1.366(6) . ? C15 H15 0.9300 . ? C16 C17 1.387(5) . ? C16 H16 0.9300 . ? C17 C19 1.502(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.353(5) . ? C20 O3 1.354(4) . ? C20 C25 1.424(5) . ? C21 C22 1.414(5) . ? C21 H21 0.9300 . ? C22 C23 1.349(5) . ? C22 H22 0.9300 . ? C23 C24 1.410(5) . ? C23 H23 0.9300 . ? C24 C25 1.409(5) . ? C24 C26 1.413(5) . ? C25 N3 1.364(4) . ? C26 C27 1.366(6) . ? C26 H26 0.9300 . ? C27 C28 1.377(6) . ? C27 H27 0.9300 . ? C28 N3 1.315(5) . ? C28 H28 0.9300 . ? C29 O3 1.434(4) . ? C29 C30 1.499(5) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 O4 1.230(4) . ? C30 N4 1.328(5) . ? C31 C32 1.390(5) . ? C31 C36 1.397(5) . ? C31 N4 1.435(5) . ? C32 C33 1.393(5) . ? C32 C38 1.499(5) . ? C33 C34 1.370(6) . ? C33 H33 0.9300 . ? C34 C35 1.363(6) . ? C34 H34 0.9300 . ? C35 C36 1.381(6) . ? C35 H35 0.9300 . ? C36 C37 1.502(6) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? N1 H1N 0.88(4) . ? N2 H2N 0.94(4) . ? N3 H3N 0.89(3) . ? N4 H4N 0.79(4) . ? N5 O6 1.204(5) . ? N5 O7 1.212(5) . ? N5 O5 1.245(4) . ? N6 O9 1.187(5) . ? N6 O10 1.233(5) . ? N6 O8 1.258(4) . ? 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 O1 126.9(3) . . ? C2 C1 C6 118.4(3) . . ? O1 C1 C6 114.7(3) . . ? C1 C2 C3 121.2(4) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 121.2(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.7(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 119.2(4) . . ? C4 C5 C7 123.9(4) . . ? C6 C5 C7 117.0(4) . . ? N1 C6 C5 119.1(4) . . ? N1 C6 C1 120.6(3) . . ? C5 C6 C1 120.2(3) . . ? C8 C7 C5 121.0(4) . . ? C8 C7 H7 119.5 . . ? C5 C7 H7 119.5 . . ? C7 C8 C9 119.8(4) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? N1 C9 C8 120.3(4) . . ? N1 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? O1 C10 C11 113.8(3) . . ? O1 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? O1 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? O2 C11 N2 124.4(3) . . ? O2 C11 C10 116.5(3) . . ? N2 C11 C10 119.2(3) . . ? C13 C12 C17 121.4(3) . . ? C13 C12 N2 120.0(4) . . ? C17 C12 N2 118.6(3) . . ? C14 C13 C12 118.5(4) . . ? C14 C13 C18 120.5(4) . . ? C12 C13 C18 121.0(4) . . ? C15 C14 C13 120.8(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C14 119.9(4) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 121.8(4) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C16 C17 C12 117.6(4) . . ? C16 C17 C19 121.0(4) . . ? C12 C17 C19 121.5(3) . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 O3 127.4(3) . . ? C21 C20 C25 119.0(3) . . ? O3 C20 C25 113.6(3) . . ? C20 C21 C22 120.2(4) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 121.8(4) . . ? C23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C22 C23 C24 119.9(4) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 118.5(3) . . ? C25 C24 C26 117.5(4) . . ? C23 C24 C26 124.0(4) . . ? N3 C25 C24 119.1(3) . . ? N3 C25 C20 120.4(3) . . ? C24 C25 C20 120.5(3) . . ? C27 C26 C24 120.6(4) . . ? C27 C26 H26 119.7 . . ? C24 C26 H26 119.7 . . ? C26 C27 C28 119.3(4) . . ? C26 C27 H27 120.4 . . ? C28 C27 H27 120.4 . . ? N3 C28 C27 121.1(4) . . ? N3 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? O3 C29 C30 111.2(3) . . ? O3 C29 H29A 109.4 . . ? C30 C29 H29A 109.4 . . ? O3 C29 H29B 109.4 . . ? C30 C29 H29B 109.4 . . ? H29A C29 H29B 108.0 . . ? O4 C30 N4 123.7(4) . . ? O4 C30 C29 117.8(4) . . ? N4 C30 C29 118.5(3) . . ? C32 C31 C36 122.5(4) . . ? C32 C31 N4 118.5(3) . . ? C36 C31 N4 119.0(4) . . ? C31 C32 C33 117.0(4) . . ? C31 C32 C38 121.1(4) . . ? C33 C32 C38 121.8(4) . . ? C34 C33 C32 121.2(4) . . ? C34 C33 H33 119.4 . . ? C32 C33 H33 119.4 . . ? C35 C34 C33 120.2(4) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C34 C35 C36 121.5(4) . . ? C34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? C35 C36 C31 117.4(4) . . ? C35 C36 C37 120.8(4) . . ? C31 C36 C37 121.6(4) . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C32 C38 H38A 109.5 . . ? C32 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C32 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C9 N1 C6 122.8(4) . . ? C9 N1 H1N 117(2) . . ? C6 N1 H1N 120(2) . . ? C11 N2 C12 120.9(3) . . ? C11 N2 H2N 121(2) . . ? C12 N2 H2N 118(2) . . ? C28 N3 C25 122.5(4) . . ? C28 N3 H3N 119(2) . . ? C25 N3 H3N 118(2) . . ? C30 N4 C31 122.9(3) . . ? C30 N4 H4N 116(3) . . ? C31 N4 H4N 121(3) . . ? O6 N5 O7 121.0(5) . . ? O6 N5 O5 118.9(4) . . ? O7 N5 O5 120.1(4) . . ? O9 N6 O10 119.8(5) . . ? O9 N6 O8 124.2(4) . . ? O10 N6 O8 116.0(4) . . ? C1 O1 C10 116.5(3) . . ? C20 O3 C29 116.5(3) . . ? 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 O1 C1 C2 C3 178.3(4) . . . . ? C6 C1 C2 C3 -0.9(6) . . . . ? C1 C2 C3 C4 0.2(7) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C3 C4 C5 C6 -1.2(6) . . . . ? C3 C4 C5 C7 178.0(4) . . . . ? C4 C5 C6 N1 179.5(4) . . . . ? C7 C5 C6 N1 0.3(5) . . . . ? C4 C5 C6 C1 0.5(6) . . . . ? C7 C5 C6 C1 -178.8(4) . . . . ? C2 C1 C6 N1 -178.5(4) . . . . ? O1 C1 C6 N1 2.2(5) . . . . ? C2 C1 C6 C5 0.6(6) . . . . ? O1 C1 C6 C5 -178.7(3) . . . . ? C4 C5 C7 C8 -178.7(5) . . . . ? C6 C5 C7 C8 0.5(7) . . . . ? C5 C7 C8 C9 -0.2(8) . . . . ? C7 C8 C9 N1 -1.0(8) . . . . ? O1 C10 C11 O2 175.4(4) . . . . ? O1 C10 C11 N2 -3.2(5) . . . . ? C17 C12 C13 C14 3.0(6) . . . . ? N2 C12 C13 C14 -175.6(4) . . . . ? C17 C12 C13 C18 -176.4(4) . . . . ? N2 C12 C13 C18 5.0(6) . . . . ? C12 C13 C14 C15 -2.4(6) . . . . ? C18 C13 C14 C15 177.0(4) . . . . ? C13 C14 C15 C16 0.4(6) . . . . ? C14 C15 C16 C17 1.1(6) . . . . ? C15 C16 C17 C12 -0.5(6) . . . . ? C15 C16 C17 C19 178.6(4) . . . . ? C13 C12 C17 C16 -1.5(6) . . . . ? N2 C12 C17 C16 177.0(3) . . . . ? C13 C12 C17 C19 179.4(4) . . . . ? N2 C12 C17 C19 -2.1(6) . . . . ? O3 C20 C21 C22 -178.9(4) . . . . ? C25 C20 C21 C22 0.2(6) . . . . ? C20 C21 C22 C23 0.0(7) . . . . ? C21 C22 C23 C24 -0.2(7) . . . . ? C22 C23 C24 C25 0.2(6) . . . . ? C22 C23 C24 C26 179.7(4) . . . . ? C23 C24 C25 N3 179.8(3) . . . . ? C26 C24 C25 N3 0.2(5) . . . . ? C23 C24 C25 C20 0.0(5) . . . . ? C26 C24 C25 C20 -179.6(4) . . . . ? C21 C20 C25 N3 180.0(4) . . . . ? O3 C20 C25 N3 -0.8(5) . . . . ? C21 C20 C25 C24 -0.2(6) . . . . ? O3 C20 C25 C24 179.0(3) . . . . ? C25 C24 C26 C27 0.8(6) . . . . ? C23 C24 C26 C27 -178.7(4) . . . . ? C24 C26 C27 C28 -1.1(7) . . . . ? C26 C27 C28 N3 0.4(7) . . . . ? O3 C29 C30 O4 -175.4(4) . . . . ? O3 C29 C30 N4 2.9(6) . . . . ? C36 C31 C32 C33 4.4(5) . . . . ? N4 C31 C32 C33 -176.0(3) . . . . ? C36 C31 C32 C38 -173.3(4) . . . . ? N4 C31 C32 C38 6.3(5) . . . . ? C31 C32 C33 C34 -1.3(6) . . . . ? C38 C32 C33 C34 176.4(4) . . . . ? C32 C33 C34 C35 -1.6(6) . . . . ? C33 C34 C35 C36 1.5(7) . . . . ? C34 C35 C36 C31 1.5(6) . . . . ? C34 C35 C36 C37 -174.4(4) . . . . ? C32 C31 C36 C35 -4.5(6) . . . . ? N4 C31 C36 C35 175.9(3) . . . . ? C32 C31 C36 C37 171.3(4) . . . . ? N4 C31 C36 C37 -8.3(6) . . . . ? C8 C9 N1 C6 1.8(7) . . . . ? C5 C6 N1 C9 -1.5(6) . . . . ? C1 C6 N1 C9 177.6(4) . . . . ? O2 C11 N2 C12 -2.4(6) . . . . ? C10 C11 N2 C12 176.0(4) . . . . ? C13 C12 N2 C11 65.7(5) . . . . ? C17 C12 N2 C11 -112.9(4) . . . . ? C27 C28 N3 C25 0.7(6) . . . . ? C24 C25 N3 C28 -1.0(6) . . . . ? C20 C25 N3 C28 178.8(4) . . . . ? O4 C30 N4 C31 4.2(7) . . . . ? C29 C30 N4 C31 -174.0(4) . . . . ? C32 C31 N4 C30 109.8(4) . . . . ? C36 C31 N4 C30 -70.6(5) . . . . ? C2 C1 O1 C10 18.6(6) . . . . ? C6 C1 O1 C10 -162.2(3) . . . . ? C11 C10 O1 C1 -168.4(3) . . . . ? C21 C20 O3 C29 -3.3(6) . . . . ? C25 C20 O3 C29 177.6(4) . . . . ? C30 C29 O3 C20 -179.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.428 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.044 # Attachment 'qdmaso4.cif' data_quiniso4 _database_code_depnum_ccdc_archive 'CCDC 622168' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H40 N4 O13 S2' _chemical_formula_weight 824.86 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' S S 0.1246 0.1234 '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 11.1900(2) _cell_length_b 11.3769(2) _cell_length_c 17.1563(4) _cell_angle_alpha 80.8950(10) _cell_angle_beta 76.1410(10) _cell_angle_gamma 65.6150(10) _cell_volume 1927.02(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3389 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.76 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.210 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12342 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6109 _reflns_number_gt 4702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0875P)^2^+2.4167P] 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_number_reflns 6109 _refine_ls_number_parameters 542 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1846 _refine_ls_wR_factor_gt 0.1673 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.014 _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 S1 S 0.72348(10) 0.82891(8) 0.22196(5) 0.0418(3) Uani 1 1 d . . . S2 S 0.57577(12) 0.17990(11) 0.05711(8) 0.0618(3) Uani 1 1 d . . . C1 C 0.6410(3) 0.8029(3) 0.5441(2) 0.0354(8) Uani 1 1 d . . . C2 C 0.6131(4) 0.7876(3) 0.6262(2) 0.0428(9) Uani 1 1 d . . . C3 C 0.6050(4) 0.8811(3) 0.6739(2) 0.0489(9) Uani 1 1 d . . . H3 H 0.5849 0.8688 0.7296 0.059 Uiso 1 1 calc R . . C4 C 0.6258(4) 0.9890(3) 0.6403(2) 0.0470(9) Uani 1 1 d . . . H4 H 0.6207 1.0494 0.6730 0.056 Uiso 1 1 calc R . . C5 C 0.6553(3) 1.0094(3) 0.5558(2) 0.0383(8) Uani 1 1 d . . . C6 C 0.6628(3) 0.9151(3) 0.5077(2) 0.0332(7) Uani 1 1 d . . . C7 C 0.7112(4) 1.0384(3) 0.3896(2) 0.0445(9) Uani 1 1 d . . . H7 H 0.7303 1.0476 0.3337 0.053 Uiso 1 1 calc R . . C8 C 0.7041(4) 1.1340(3) 0.4345(2) 0.0482(9) Uani 1 1 d . . . H8 H 0.7182 1.2068 0.4087 0.058 Uiso 1 1 calc R . . C9 C 0.6765(4) 1.1201(3) 0.5158(2) 0.0442(9) Uani 1 1 d . . . H9 H 0.6714 1.1838 0.5458 0.053 Uiso 1 1 calc R . . C10 C 0.6368(4) 0.6017(3) 0.5265(2) 0.0389(8) Uani 1 1 d . . . H10A H 0.5469 0.6215 0.5577 0.047 Uiso 1 1 calc R . . H10B H 0.6990 0.5591 0.5628 0.047 Uiso 1 1 calc R . . C11 C 0.6995(4) 0.4725(3) 0.3243(2) 0.0436(9) Uani 1 1 d . . . C12 C 0.8175(4) 0.3637(3) 0.3057(2) 0.0481(9) Uani 1 1 d . . . C13 C 0.8212(5) 0.2831(4) 0.2510(2) 0.0583(11) Uani 1 1 d . . . H13 H 0.8982 0.2097 0.2374 0.070 Uiso 1 1 calc R . . C14 C 0.7128(5) 0.3105(4) 0.2169(2) 0.0635(12) Uani 1 1 d . . . H14 H 0.7165 0.2544 0.1816 0.076 Uiso 1 1 calc R . . C15 C 0.5992(5) 0.4194(4) 0.2342(2) 0.0595(11) Uani 1 1 d . . . H15 H 0.5273 0.4371 0.2098 0.071 Uiso 1 1 calc R . . C16 C 0.5897(4) 0.5048(4) 0.2882(2) 0.0495(10) Uani 1 1 d . . . C17 C 0.9341(5) 0.3321(4) 0.3453(3) 0.0661(12) Uani 1 1 d . . . H17A H 0.9108 0.3091 0.4014 0.099 Uiso 1 1 calc R . . H17B H 0.9568 0.4062 0.3392 0.099 Uiso 1 1 calc R . . H17C H 1.0094 0.2609 0.3204 0.099 Uiso 1 1 calc R . . C18 C 0.4659(5) 0.6246(4) 0.3066(3) 0.0642(12) Uani 1 1 d . . . H18A H 0.4029 0.6310 0.2752 0.096 Uiso 1 1 calc R . . H18B H 0.4885 0.6991 0.2938 0.096 Uiso 1 1 calc R . . H18C H 0.4269 0.6206 0.3628 0.096 Uiso 1 1 calc R . . C19 C 0.0596(4) 0.3863(3) 0.1165(2) 0.0478(9) Uani 1 1 d . . . C20 C 0.1594(5) 0.2662(4) 0.1001(3) 0.0616(11) Uani 1 1 d . . . H20 H 0.2382 0.2383 0.1195 0.074 Uiso 1 1 calc R . . C21 C 0.1395(6) 0.1859(4) 0.0532(3) 0.0735(14) Uani 1 1 d . . . H21 H 0.2063 0.1046 0.0426 0.088 Uiso 1 1 calc R . . C22 C 0.0268(6) 0.2240(4) 0.0235(3) 0.0712(14) Uani 1 1 d . . . H22 H 0.0175 0.1693 -0.0074 0.085 Uiso 1 1 calc R . . C23 C -0.0769(5) 0.3461(4) 0.0392(2) 0.0560(11) Uani 1 1 d . . . C24 C -0.0587(4) 0.4279(3) 0.0861(2) 0.0456(9) Uani 1 1 d . . . C25 C -0.2719(5) 0.5878(4) 0.0752(2) 0.0580(11) Uani 1 1 d . . . H25 H -0.3368 0.6695 0.0871 0.070 Uiso 1 1 calc R . . C26 C -0.2953(5) 0.5110(5) 0.0299(3) 0.0678(13) Uani 1 1 d . . . H26 H -0.3756 0.5400 0.0121 0.081 Uiso 1 1 calc R . . C27 C -0.1977(6) 0.3922(5) 0.0121(3) 0.0670(13) Uani 1 1 d . . . H27 H -0.2119 0.3406 -0.0187 0.080 Uiso 1 1 calc R . . C28 C 0.1793(4) 0.4290(3) 0.1980(2) 0.0494(9) Uani 1 1 d . . . H28A H 0.2587 0.4120 0.1560 0.059 Uiso 1 1 calc R . . H28B H 0.1876 0.3483 0.2296 0.059 Uiso 1 1 calc R . . C29 C 0.0655(4) 0.7441(3) 0.2955(2) 0.0441(9) Uani 1 1 d . . . C30 C 0.0960(5) 0.8442(4) 0.2501(3) 0.0583(11) Uani 1 1 d . . . C31 C 0.0959(5) 0.9403(4) 0.2915(3) 0.0695(13) Uani 1 1 d . . . H31 H 0.1170 1.0079 0.2627 0.083 Uiso 1 1 calc R . . C32 C 0.0653(5) 0.9371(4) 0.3737(3) 0.0715(14) Uani 1 1 d . . . H32 H 0.0658 1.0021 0.4002 0.086 Uiso 1 1 calc R . . C33 C 0.0338(5) 0.8378(4) 0.4172(3) 0.0633(12) Uani 1 1 d . . . H33 H 0.0132 0.8364 0.4731 0.076 Uiso 1 1 calc R . . C34 C 0.0323(4) 0.7396(4) 0.3791(2) 0.0487(9) Uani 1 1 d . . . C35 C 0.1286(7) 0.8487(6) 0.1600(3) 0.0967(19) Uani 1 1 d . . . H35A H 0.1409 0.9273 0.1393 0.145 Uiso 1 1 calc R . . H35B H 0.0565 0.8460 0.1403 0.145 Uiso 1 1 calc R . . H35C H 0.2092 0.7758 0.1427 0.145 Uiso 1 1 calc R . . C36 C -0.0040(5) 0.6330(4) 0.4270(3) 0.0656(12) Uani 1 1 d . . . H36A H -0.0756 0.6273 0.4083 0.098 Uiso 1 1 calc R . . H36B H -0.0320 0.6508 0.4828 0.098 Uiso 1 1 calc R . . H36C H 0.0724 0.5525 0.4205 0.098 Uiso 1 1 calc R . . C39 C 0.1719(4) 0.5266(3) 0.2517(2) 0.0460(9) Uani 1 1 d . . . C40 C 0.6631(4) 0.5118(3) 0.4632(2) 0.0386(8) Uani 1 1 d . . . H2 H 0.602(4) 0.718(4) 0.649(2) 0.045(10) Uiso 1 1 d . . . H1N H 0.697(4) 0.871(4) 0.393(3) 0.069(13) Uiso 1 1 d . . . H2N H 0.687(3) 0.619(3) 0.373(2) 0.034(9) Uiso 1 1 d . . . H3N H -0.152(4) 0.603(4) 0.132(2) 0.055(11) Uiso 1 1 d . . . H4N H 0.011(4) 0.658(4) 0.223(3) 0.059(12) Uiso 1 1 d . . . H5O H 0.729(9) 1.003(8) 0.160(5) 0.19(4) Uiso 1 1 d . . . N1 N 0.6909(3) 0.9348(2) 0.42587(17) 0.0361(6) Uani 1 1 d . . . N2 N 0.6875(3) 0.5515(3) 0.38568(18) 0.0435(8) Uani 1 1 d . . . N3 N -0.1584(3) 0.5460(3) 0.10164(19) 0.0474(8) Uani 1 1 d . . . N4 N 0.0704(3) 0.6420(3) 0.2534(2) 0.0460(8) Uani 1 1 d . . . O1 O 0.6505(2) 0.7199(2) 0.49148(13) 0.0395(6) Uani 1 1 d . . . O2 O 0.6615(3) 0.4050(2) 0.48599(15) 0.0552(7) Uani 1 1 d . . . O3 O 0.0651(3) 0.4723(2) 0.16194(16) 0.0495(6) Uani 1 1 d . . . O4 O 0.2600(3) 0.4939(3) 0.29035(19) 0.0646(8) Uani 1 1 d . . . O5 O 0.7234(3) 0.9616(3) 0.21045(19) 0.0673(9) Uani 1 1 d . . . O6 O 0.7150(3) 0.7913(2) 0.30703(15) 0.0610(8) Uani 1 1 d . . . O7 O 0.8448(3) 0.7418(2) 0.17429(16) 0.0537(7) Uani 1 1 d . . . O8 O 0.6071(3) 0.8313(4) 0.1955(2) 0.0883(11) Uani 1 1 d . . . O9 O 0.7095(4) 0.0935(4) 0.0739(2) 0.0944(12) Uani 1 1 d . . . O10 O 0.5285(9) 0.1164(11) 0.0194(9) 0.340(8) Uani 1 1 d . . . H10O H 0.5155 0.0578 0.0499 0.509 Uiso 1 1 calc R . . O11 O 0.4858(5) 0.2273(7) 0.1243(3) 0.198(3) Uani 1 1 d . . . O12 O 0.5892(6) 0.2675(8) -0.0007(5) 0.254(5) Uani 1 1 d . . . O13 O 0.4194(6) 0.9691(5) 0.1259(4) 0.156(2) 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 S1 0.0489(6) 0.0396(5) 0.0360(5) -0.0044(3) -0.0113(4) -0.0140(4) S2 0.0594(7) 0.0600(6) 0.0715(8) -0.0097(5) -0.0150(6) -0.0257(5) C1 0.040(2) 0.0272(15) 0.041(2) -0.0063(13) -0.0077(16) -0.0138(14) C2 0.057(2) 0.0334(17) 0.040(2) -0.0003(15) -0.0087(18) -0.0210(17) C3 0.063(3) 0.047(2) 0.037(2) -0.0073(16) -0.0083(19) -0.0210(18) C4 0.057(2) 0.0411(19) 0.047(2) -0.0156(16) -0.0094(19) -0.0185(17) C5 0.037(2) 0.0310(16) 0.048(2) -0.0106(14) -0.0066(17) -0.0128(14) C6 0.0329(19) 0.0306(15) 0.038(2) -0.0073(13) -0.0059(15) -0.0130(13) C7 0.054(2) 0.0364(17) 0.045(2) -0.0019(15) -0.0037(18) -0.0227(17) C8 0.054(2) 0.0329(17) 0.060(3) -0.0028(16) -0.003(2) -0.0239(17) C9 0.046(2) 0.0335(17) 0.059(3) -0.0120(16) -0.0072(19) -0.0198(16) C10 0.051(2) 0.0282(15) 0.041(2) -0.0016(13) -0.0084(17) -0.0192(15) C11 0.066(3) 0.0376(18) 0.035(2) -0.0041(14) -0.0020(19) -0.0317(18) C12 0.065(3) 0.0425(19) 0.041(2) -0.0026(16) 0.0006(19) -0.0305(19) C13 0.083(3) 0.043(2) 0.046(2) -0.0087(17) 0.008(2) -0.032(2) C14 0.099(4) 0.066(3) 0.043(2) -0.015(2) -0.003(3) -0.051(3) C15 0.081(3) 0.072(3) 0.044(2) -0.006(2) -0.011(2) -0.048(3) C16 0.068(3) 0.049(2) 0.043(2) -0.0030(16) -0.007(2) -0.037(2) C17 0.065(3) 0.062(3) 0.070(3) -0.006(2) -0.007(2) -0.026(2) C18 0.068(3) 0.061(3) 0.071(3) -0.007(2) -0.015(2) -0.031(2) C19 0.065(3) 0.0397(18) 0.040(2) -0.0105(15) 0.002(2) -0.0258(18) C20 0.073(3) 0.044(2) 0.061(3) -0.0158(19) 0.000(2) -0.020(2) C21 0.103(4) 0.045(2) 0.064(3) -0.020(2) 0.003(3) -0.025(2) C22 0.118(4) 0.055(2) 0.050(3) -0.021(2) -0.002(3) -0.044(3) C23 0.089(3) 0.054(2) 0.038(2) -0.0079(17) -0.003(2) -0.043(2) C24 0.067(3) 0.0458(19) 0.0308(19) -0.0068(15) -0.0012(19) -0.0317(19) C25 0.067(3) 0.065(2) 0.050(2) -0.0043(19) -0.017(2) -0.030(2) C26 0.086(4) 0.084(3) 0.052(3) -0.002(2) -0.024(3) -0.047(3) C27 0.106(4) 0.077(3) 0.045(2) -0.005(2) -0.016(3) -0.062(3) C28 0.047(2) 0.0414(19) 0.057(2) -0.0090(17) -0.008(2) -0.0136(17) C29 0.041(2) 0.0370(17) 0.056(2) -0.0088(16) -0.0188(19) -0.0107(15) C30 0.070(3) 0.049(2) 0.060(3) -0.0038(19) -0.015(2) -0.026(2) C31 0.082(3) 0.052(2) 0.089(4) -0.007(2) -0.027(3) -0.033(2) C32 0.073(3) 0.053(2) 0.099(4) -0.026(2) -0.036(3) -0.017(2) C33 0.065(3) 0.068(3) 0.057(3) -0.019(2) -0.021(2) -0.015(2) C34 0.041(2) 0.051(2) 0.052(2) -0.0084(17) -0.0167(19) -0.0101(17) C35 0.144(6) 0.084(4) 0.072(4) 0.002(3) -0.007(4) -0.064(4) C36 0.065(3) 0.072(3) 0.056(3) -0.001(2) -0.006(2) -0.027(2) C39 0.044(2) 0.0404(19) 0.054(2) -0.0024(16) -0.009(2) -0.0168(17) C40 0.047(2) 0.0313(16) 0.042(2) -0.0042(14) -0.0065(17) -0.0210(15) N1 0.0433(17) 0.0283(13) 0.0385(17) -0.0060(11) -0.0052(14) -0.0157(12) N2 0.070(2) 0.0317(15) 0.0399(18) -0.0008(12) -0.0099(15) -0.0324(15) N3 0.061(2) 0.0475(17) 0.0384(18) -0.0102(14) -0.0070(16) -0.0251(16) N4 0.048(2) 0.0393(16) 0.054(2) -0.0084(13) -0.0204(17) -0.0131(14) O1 0.0597(16) 0.0304(11) 0.0367(13) -0.0035(9) -0.0080(12) -0.0260(11) O2 0.092(2) 0.0346(13) 0.0466(15) -0.0036(11) -0.0031(14) -0.0375(14) O3 0.0544(17) 0.0408(13) 0.0547(16) -0.0143(11) -0.0117(13) -0.0153(12) O4 0.0564(18) 0.0514(15) 0.087(2) -0.0080(14) -0.0344(17) -0.0095(13) O5 0.096(2) 0.0401(14) 0.0539(19) 0.0032(13) -0.0105(17) -0.0196(15) O6 0.108(2) 0.0456(14) 0.0373(15) -0.0024(11) -0.0122(15) -0.0391(15) O7 0.0534(17) 0.0513(15) 0.0535(17) -0.0202(12) -0.0100(14) -0.0118(12) O8 0.058(2) 0.139(3) 0.076(2) -0.026(2) -0.0174(18) -0.038(2) O9 0.071(2) 0.098(3) 0.069(2) 0.0035(19) -0.0075(19) 0.0052(19) O10 0.209(9) 0.306(12) 0.59(2) -0.247(14) -0.142(11) -0.071(9) O11 0.091(4) 0.270(7) 0.091(4) -0.028(4) 0.002(3) 0.064(4) O12 0.105(4) 0.279(9) 0.246(8) 0.174(7) -0.027(5) -0.015(5) O13 0.132(4) 0.125(4) 0.212(6) 0.001(4) -0.030(4) -0.057(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 S1 O6 1.446(3) . ? S1 O7 1.452(3) . ? S1 O8 1.467(3) . ? S1 O5 1.490(3) . ? S2 O12 1.319(6) . ? S2 O11 1.352(5) . ? S2 O10 1.360(7) . ? S2 O9 1.480(4) . ? C1 O1 1.363(4) . ? C1 C2 1.366(5) . ? C1 C6 1.418(4) . ? C2 C3 1.403(5) . ? C2 H2 0.87(4) . ? C3 C4 1.357(5) . ? C3 H3 0.9300 . ? C4 C5 1.412(5) . ? C4 H4 0.9300 . ? C5 C9 1.417(5) . ? C5 C6 1.418(4) . ? C6 N1 1.366(4) . ? C7 N1 1.322(4) . ? C7 C8 1.396(5) . ? C7 H7 0.9300 . ? C8 C9 1.354(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O1 1.437(3) . ? C10 C40 1.504(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.396(5) . ? C11 C16 1.396(5) . ? C11 N2 1.437(4) . ? C12 C13 1.396(5) . ? C12 C17 1.501(6) . ? C13 C14 1.370(6) . ? C13 H13 0.9300 . ? C14 C15 1.369(6) . ? C14 H14 0.9300 . ? C15 C16 1.402(5) . ? C15 H15 0.9300 . ? C16 C18 1.498(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 O3 1.372(4) . ? C19 C20 1.380(5) . ? C19 C24 1.409(6) . ? C20 C21 1.420(6) . ? C20 H20 0.9300 . ? C21 C22 1.351(7) . ? C21 H21 0.9300 . ? C22 C23 1.409(6) . ? C22 H22 0.9300 . ? C23 C27 1.399(7) . ? C23 C24 1.423(5) . ? C24 N3 1.362(5) . ? C25 N3 1.324(5) . ? C25 C26 1.392(6) . ? C25 H25 0.9300 . ? C26 C27 1.366(7) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 O3 1.421(4) . ? C28 C39 1.516(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.390(5) . ? C29 C34 1.391(5) . ? C29 N4 1.438(4) . ? C30 C31 1.394(6) . ? C30 C35 1.499(7) . ? C31 C32 1.368(7) . ? C31 H31 0.9300 . ? C32 C33 1.376(7) . ? C32 H32 0.9300 . ? C33 C34 1.389(6) . ? C33 H33 0.9300 . ? C34 C36 1.497(6) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C39 O4 1.218(4) . ? C39 N4 1.334(5) . ? C40 O2 1.222(4) . ? C40 N2 1.336(4) . ? N1 H1N 0.96(4) . ? N2 H2N 0.77(4) . ? N3 H3N 0.92(4) . ? N4 H4N 0.88(4) . ? O5 H5O 0.91(9) . ? O10 H10O 0.8200 . ? 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 O6 S1 O7 111.79(17) . . ? O6 S1 O8 110.1(2) . . ? O7 S1 O8 109.24(18) . . ? O6 S1 O5 106.92(16) . . ? O7 S1 O5 109.34(18) . . ? O8 S1 O5 109.4(2) . . ? O12 S2 O11 115.3(5) . . ? O12 S2 O10 99.8(8) . . ? O11 S2 O10 109.0(7) . . ? O12 S2 O9 108.9(3) . . ? O11 S2 O9 112.7(3) . . ? O10 S2 O9 110.4(5) . . ? O1 C1 C2 126.5(3) . . ? O1 C1 C6 114.8(3) . . ? C2 C1 C6 118.6(3) . . ? C1 C2 C3 121.0(3) . . ? C1 C2 H2 119(2) . . ? C3 C2 H2 120(2) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C9 123.6(3) . . ? C4 C5 C6 118.6(3) . . ? C9 C5 C6 117.7(3) . . ? N1 C6 C1 120.8(3) . . ? N1 C6 C5 118.7(3) . . ? C1 C6 C5 120.4(3) . . ? N1 C7 C8 120.5(3) . . ? N1 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 119.5(3) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C5 120.8(3) . . ? C8 C9 H9 119.6 . . ? C5 C9 H9 119.6 . . ? O1 C10 C40 111.6(3) . . ? O1 C10 H10A 109.3 . . ? C40 C10 H10A 109.3 . . ? O1 C10 H10B 109.3 . . ? C40 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C16 122.6(3) . . ? C12 C11 N2 119.1(3) . . ? C16 C11 N2 118.2(3) . . ? C13 C12 C11 117.5(4) . . ? C13 C12 C17 121.2(4) . . ? C11 C12 C17 121.3(3) . . ? C14 C13 C12 120.9(4) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 120.9(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 121.0(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C11 C16 C15 117.1(4) . . ? C11 C16 C18 121.8(3) . . ? C15 C16 C18 121.0(4) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 C20 124.7(4) . . ? O3 C19 C24 115.3(3) . . ? C20 C19 C24 119.9(3) . . ? C19 C20 C21 118.8(5) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C22 C21 C20 122.1(4) . . ? C22 C21 H21 119.0 . . ? C20 C21 H21 119.0 . . ? C21 C22 C23 120.5(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C27 C23 C22 124.2(4) . . ? C27 C23 C24 117.6(4) . . ? C22 C23 C24 118.2(4) . . ? N3 C24 C19 120.8(3) . . ? N3 C24 C23 118.7(4) . . ? C19 C24 C23 120.5(4) . . ? N3 C25 C26 120.8(4) . . ? N3 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C27 C26 C25 118.6(4) . . ? C27 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? C26 C27 C23 121.6(4) . . ? C26 C27 H27 119.2 . . ? C23 C27 H27 119.2 . . ? O3 C28 C39 112.5(3) . . ? O3 C28 H28A 109.1 . . ? C39 C28 H28A 109.1 . . ? O3 C28 H28B 109.1 . . ? C39 C28 H28B 109.1 . . ? H28A C28 H28B 107.8 . . ? C30 C29 C34 122.3(3) . . ? C30 C29 N4 117.9(4) . . ? C34 C29 N4 119.8(3) . . ? C29 C30 C31 117.5(4) . . ? C29 C30 C35 121.4(4) . . ? C31 C30 C35 121.0(4) . . ? C32 C31 C30 121.2(4) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C31 C32 C33 120.1(4) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C32 C33 C34 121.1(4) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C33 C34 C29 117.7(4) . . ? C33 C34 C36 120.7(4) . . ? C29 C34 C36 121.6(3) . . ? C30 C35 H35A 109.5 . . ? C30 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C30 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O4 C39 N4 124.3(3) . . ? O4 C39 C28 117.3(3) . . ? N4 C39 C28 118.3(3) . . ? O2 C40 N2 123.4(3) . . ? O2 C40 C10 117.6(3) . . ? N2 C40 C10 119.0(3) . . ? C7 N1 C6 122.7(3) . . ? C7 N1 H1N 118(3) . . ? C6 N1 H1N 119(3) . . ? C40 N2 C11 119.9(3) . . ? C40 N2 H2N 122(3) . . ? C11 N2 H2N 118(3) . . ? C25 N3 C24 122.7(3) . . ? C25 N3 H3N 115(3) . . ? C24 N3 H3N 122(3) . . ? C39 N4 C29 121.2(3) . . ? C39 N4 H4N 118(3) . . ? C29 N4 H4N 120(3) . . ? C1 O1 C10 116.1(2) . . ? C19 O3 C28 116.3(3) . . ? S1 O5 H5O 121(5) . . ? S2 O10 H10O 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.5(3) . . . . ? C6 C1 C2 C3 0.5(5) . . . . ? C1 C2 C3 C4 -0.7(6) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C3 C4 C5 C9 179.1(4) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? O1 C1 C6 N1 0.1(5) . . . . ? C2 C1 C6 N1 -179.9(3) . . . . ? O1 C1 C6 C5 179.8(3) . . . . ? C2 C1 C6 C5 -0.2(5) . . . . ? C4 C5 C6 N1 179.8(3) . . . . ? C9 C5 C6 N1 0.4(5) . . . . ? C4 C5 C6 C1 0.1(5) . . . . ? C9 C5 C6 C1 -179.3(3) . . . . ? N1 C7 C8 C9 0.1(6) . . . . ? C7 C8 C9 C5 0.2(6) . . . . ? C4 C5 C9 C8 -179.8(4) . . . . ? C6 C5 C9 C8 -0.5(5) . . . . ? C16 C11 C12 C13 -2.5(5) . . . . ? N2 C11 C12 C13 174.5(3) . . . . ? C16 C11 C12 C17 179.6(3) . . . . ? N2 C11 C12 C17 -3.4(5) . . . . ? C11 C12 C13 C14 0.2(5) . . . . ? C17 C12 C13 C14 178.0(4) . . . . ? C12 C13 C14 C15 1.6(6) . . . . ? C13 C14 C15 C16 -1.1(6) . . . . ? C12 C11 C16 C15 3.0(5) . . . . ? N2 C11 C16 C15 -174.1(3) . . . . ? C12 C11 C16 C18 -177.6(3) . . . . ? N2 C11 C16 C18 5.4(5) . . . . ? C14 C15 C16 C11 -1.1(5) . . . . ? C14 C15 C16 C18 179.4(4) . . . . ? O3 C19 C20 C21 179.0(4) . . . . ? C24 C19 C20 C21 -0.7(6) . . . . ? C19 C20 C21 C22 0.7(7) . . . . ? C20 C21 C22 C23 -0.6(7) . . . . ? C21 C22 C23 C27 -178.8(4) . . . . ? C21 C22 C23 C24 0.6(6) . . . . ? O3 C19 C24 N3 0.2(5) . . . . ? C20 C19 C24 N3 179.9(3) . . . . ? O3 C19 C24 C23 -179.0(3) . . . . ? C20 C19 C24 C23 0.7(5) . . . . ? C27 C23 C24 N3 -0.4(5) . . . . ? C22 C23 C24 N3 -179.9(3) . . . . ? C27 C23 C24 C19 178.8(3) . . . . ? C22 C23 C24 C19 -0.6(5) . . . . ? N3 C25 C26 C27 -1.0(6) . . . . ? C25 C26 C27 C23 0.8(6) . . . . ? C22 C23 C27 C26 179.3(4) . . . . ? C24 C23 C27 C26 -0.1(6) . . . . ? C34 C29 C30 C31 1.7(6) . . . . ? N4 C29 C30 C31 -177.7(4) . . . . ? C34 C29 C30 C35 -178.6(5) . . . . ? N4 C29 C30 C35 2.0(6) . . . . ? C29 C30 C31 C32 -0.8(7) . . . . ? C35 C30 C31 C32 179.5(5) . . . . ? C30 C31 C32 C33 0.0(7) . . . . ? C31 C32 C33 C34 0.0(7) . . . . ? C32 C33 C34 C29 0.9(6) . . . . ? C32 C33 C34 C36 -179.1(4) . . . . ? C30 C29 C34 C33 -1.8(6) . . . . ? N4 C29 C34 C33 177.6(3) . . . . ? C30 C29 C34 C36 178.3(4) . . . . ? N4 C29 C34 C36 -2.3(6) . . . . ? O3 C28 C39 O4 174.2(3) . . . . ? O3 C28 C39 N4 -6.0(5) . . . . ? O1 C10 C40 O2 176.1(3) . . . . ? O1 C10 C40 N2 -3.6(5) . . . . ? C8 C7 N1 C6 -0.2(5) . . . . ? C1 C6 N1 C7 179.6(3) . . . . ? C5 C6 N1 C7 -0.1(5) . . . . ? O2 C40 N2 C11 6.6(6) . . . . ? C10 C40 N2 C11 -173.7(3) . . . . ? C12 C11 N2 C40 -76.8(4) . . . . ? C16 C11 N2 C40 100.4(4) . . . . ? C26 C25 N3 C24 0.4(6) . . . . ? C19 C24 N3 C25 -178.9(4) . . . . ? C23 C24 N3 C25 0.3(5) . . . . ? O4 C39 N4 C29 7.1(6) . . . . ? C28 C39 N4 C29 -172.7(3) . . . . ? C30 C29 N4 C39 104.2(4) . . . . ? C34 C29 N4 C39 -75.2(5) . . . . ? C2 C1 O1 C10 -3.6(5) . . . . ? C6 C1 O1 C10 176.4(3) . . . . ? C40 C10 O1 C1 -174.1(3) . . . . ? C20 C19 O3 C28 -4.0(5) . . . . ? C24 C19 O3 C28 175.7(3) . . . . ? C39 C28 O3 C19 -175.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.897 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.897 _refine_diff_density_max 0.970 _refine_diff_density_min -0.840 _refine_diff_density_rms 0.059 # Attachment 'qdma01.cif' data_quinam01_0m _database_code_depnum_ccdc_archive 'CCDC 622169' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H38 N4 O5' _chemical_formula_weight 630.72 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 11.4032(5) _cell_length_b 11.4631(5) _cell_length_c 15.0226(7) _cell_angle_alpha 80.782(3) _cell_angle_beta 72.286(3) _cell_angle_gamma 68.221(3) _cell_volume 1734.59(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1898 _cell_measurement_theta_min 5.37 _cell_measurement_theta_max 21.72 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 0.081 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19198 _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 5.37 _diffrn_reflns_theta_max 30.55 _reflns_number_total 9486 _reflns_number_gt 3782 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0480P)^2^+0.2755P] 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 SHELXL _refine_ls_extinction_coef 0.009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9486 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1814 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 C1 C 0.6261(2) 0.1171(2) 0.08474(14) 0.0535(5) Uani 1 1 d . . . C2 C 0.7554(2) 0.0909(2) 0.03813(17) 0.0707(7) Uani 1 1 d . . . H2 H 0.7932 0.1527 0.0285 0.085 Uiso 1 1 calc R . . C3 C 0.8314(3) -0.0295(3) 0.0047(2) 0.0876(8) Uani 1 1 d . . . H3 H 0.9195 -0.0468 -0.0266 0.105 Uiso 1 1 calc R . . C4 C 0.7785(3) -0.1205(3) 0.0172(2) 0.0878(8) Uani 1 1 d . . . H4 H 0.8304 -0.1993 -0.0059 0.105 Uiso 1 1 calc R . . C5 C 0.6461(3) -0.0976(2) 0.06482(17) 0.0667(6) Uani 1 1 d . . . C6 C 0.5683(2) 0.0217(2) 0.10074(14) 0.0548(5) Uani 1 1 d . . . C7 C 0.3881(3) -0.0393(3) 0.15871(16) 0.0732(7) Uani 1 1 d . . . H7 H 0.3005 -0.0215 0.1919 0.088 Uiso 1 1 calc R . . C8 C 0.4564(4) -0.1580(3) 0.12280(19) 0.0827(8) Uani 1 1 d . . . H8 H 0.4144 -0.2160 0.1300 0.099 Uiso 1 1 calc R . . C9 C 0.5838(3) -0.1869(2) 0.07772(19) 0.0806(8) Uani 1 1 d . . . H9 H 0.6314 -0.2664 0.0548 0.097 Uiso 1 1 calc R . . C10 C 0.5895(2) 0.3339(2) 0.09187(16) 0.0587(6) Uani 1 1 d . . . H10A H 0.6284 0.3363 0.0248 0.070 Uiso 1 1 calc R . . H10B H 0.6574 0.3207 0.1224 0.070 Uiso 1 1 calc R . . C11 C 0.4842(2) 0.4571(2) 0.11785(14) 0.0544(5) Uani 1 1 d . . . C12 C 0.2525(2) 0.5710(2) 0.18336(15) 0.0641(6) Uani 1 1 d . . . C13 C 0.1574(3) 0.5902(3) 0.13768(18) 0.0765(7) Uani 1 1 d . . . C14 C 0.0528(3) 0.7028(4) 0.1492(3) 0.1065(10) Uani 1 1 d . . . H14 H -0.0123 0.7181 0.1193 0.128 Uiso 1 1 calc R . . C15 C 0.0442(4) 0.7918(4) 0.2040(3) 0.1247(13) Uani 1 1 d . . . H15 H -0.0250 0.8681 0.2091 0.150 Uiso 1 1 calc R . . C16 C 0.1361(4) 0.7700(3) 0.2513(3) 0.1116(11) Uani 1 1 d . . . H16 H 0.1280 0.8311 0.2889 0.134 Uiso 1 1 calc R . . C17 C 0.2421(3) 0.6570(3) 0.24376(18) 0.0809(8) Uani 1 1 d . . . C18 C 0.3379(3) 0.6289(3) 0.3013(2) 0.1071(10) Uani 1 1 d . . . H18A H 0.3430 0.5505 0.3367 0.161 Uiso 1 1 calc R . . H18B H 0.3089 0.6950 0.3433 0.161 Uiso 1 1 calc R . . H18C H 0.4228 0.6234 0.2606 0.161 Uiso 1 1 calc R . . C19 C 0.1668(3) 0.4924(3) 0.0780(2) 0.0966(9) Uani 1 1 d . . . H19A H 0.2502 0.4702 0.0321 0.145 Uiso 1 1 calc R . . H19B H 0.0979 0.5253 0.0471 0.145 Uiso 1 1 calc R . . H19C H 0.1584 0.4191 0.1166 0.145 Uiso 1 1 calc R . . C20 C 0.2916(2) 0.1341(2) 0.52737(14) 0.0596(6) Uani 1 1 d . . . C21 C 0.2761(2) 0.0707(3) 0.61224(16) 0.0773(7) Uani 1 1 d . . . H21 H 0.2089 0.0375 0.6343 0.093 Uiso 1 1 calc R . . C22 C 0.3621(3) 0.0557(3) 0.66649(18) 0.0924(9) Uani 1 1 d . . . H22 H 0.3504 0.0130 0.7248 0.111 Uiso 1 1 calc R . . C23 C 0.4608(3) 0.1014(3) 0.6360(2) 0.0933(9) Uani 1 1 d . . . H23 H 0.5161 0.0904 0.6734 0.112 Uiso 1 1 calc R . . C24 C 0.4812(2) 0.1656(2) 0.54820(17) 0.0706(7) Uani 1 1 d . . . C25 C 0.3958(2) 0.1821(2) 0.49208(14) 0.0566(5) Uani 1 1 d . . . C26 C 0.5100(3) 0.2851(3) 0.37572(19) 0.0845(8) Uani 1 1 d . . . H26 H 0.5211 0.3261 0.3167 0.101 Uiso 1 1 calc R . . C27 C 0.5984(3) 0.2739(3) 0.4260(2) 0.0972(9) Uani 1 1 d . . . H27 H 0.6657 0.3069 0.4014 0.117 Uiso 1 1 calc R . . C28 C 0.5839(3) 0.2143(3) 0.5109(2) 0.0921(9) Uani 1 1 d . . . H28 H 0.6423 0.2050 0.5455 0.111 Uiso 1 1 calc R . . C29 C 0.0924(2) 0.1310(3) 0.50835(18) 0.0810(8) Uani 1 1 d . . . H29A H 0.0555 0.1554 0.5727 0.097 Uiso 1 1 calc R . . H29B H 0.1116 0.0412 0.5084 0.097 Uiso 1 1 calc R . . C30 C -0.0062(2) 0.1993(2) 0.45384(16) 0.0690(7) Uani 1 1 d . . . C31 C -0.0564(2) 0.3415(3) 0.32125(15) 0.0625(6) Uani 1 1 d . . . C32 C -0.1135(3) 0.4676(3) 0.3331(2) 0.1019(9) Uani 1 1 d . . . C33 C -0.1977(4) 0.5378(4) 0.2749(4) 0.1458(15) Uani 1 1 d . . . H33 H -0.2409 0.6238 0.2813 0.175 Uiso 1 1 calc R . . C34 C -0.2150(4) 0.4795(7) 0.2100(4) 0.148(2) Uani 1 1 d . . . H34 H -0.2714 0.5256 0.1734 0.177 Uiso 1 1 calc R . . C35 C -0.1533(5) 0.3595(6) 0.1990(3) 0.1357(16) Uani 1 1 d . . . H35 H -0.1624 0.3231 0.1515 0.163 Uiso 1 1 calc R . . C36 C -0.0760(3) 0.2855(3) 0.25422(19) 0.0883(9) Uani 1 1 d . . . C37 C -0.0135(5) 0.1443(4) 0.2444(3) 0.1628(18) Uani 1 1 d . . . H37A H -0.0454 0.1199 0.2006 0.244 Uiso 1 1 calc R . . H37B H -0.0356 0.1016 0.3041 0.244 Uiso 1 1 calc R . . H37C H 0.0800 0.1220 0.2221 0.244 Uiso 1 1 calc R . . C38 C -0.0874(6) 0.5269(4) 0.4045(4) 0.190(2) Uani 1 1 d . . . H38A H -0.1288 0.5012 0.4663 0.286 Uiso 1 1 calc R . . H38B H -0.1222 0.6169 0.3960 0.286 Uiso 1 1 calc R . . H38C H 0.0053 0.5005 0.3965 0.286 Uiso 1 1 calc R . . H2N H 0.353(2) 0.383(2) 0.1887(15) 0.063(6) Uiso 1 1 d . . . H4N H 0.113(3) 0.260(2) 0.3560(16) 0.081(8) Uiso 1 1 d . . . H1S H 0.337(3) 0.190(3) 0.229(2) 0.124(13) Uiso 1 1 d . . . H2S H 0.324(3) 0.254(3) 0.312(2) 0.123(12) Uiso 1 1 d . . . N1 N 0.43950(19) 0.04949(17) 0.14869(12) 0.0612(5) Uani 1 1 d . . . N2 N 0.36483(18) 0.45733(19) 0.16742(12) 0.0584(5) Uani 1 1 d . . . N3 N 0.41193(17) 0.24192(19) 0.40556(13) 0.0664(5) Uani 1 1 d . . . N4 N 0.0304(2) 0.26527(19) 0.37557(13) 0.0645(5) Uani 1 1 d . . . O1 O 0.54244(14) 0.23157(13) 0.11744(10) 0.0597(4) Uani 1 1 d . . . O2 O 0.51258(16) 0.55277(14) 0.09152(11) 0.0723(5) Uani 1 1 d . . . O3 O 0.21078(14) 0.15781(16) 0.47003(10) 0.0703(5) Uani 1 1 d . . . O4 O -0.11592(16) 0.1922(2) 0.48487(13) 0.0994(6) Uani 1 1 d . . . O5 O 0.28616(16) 0.25482(18) 0.26661(13) 0.0631(4) 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 0.0625(14) 0.0456(13) 0.0562(12) -0.0007(10) -0.0253(10) -0.0159(11) C2 0.0648(16) 0.0672(17) 0.0855(17) -0.0084(13) -0.0267(13) -0.0215(13) C3 0.0660(16) 0.085(2) 0.108(2) -0.0235(17) -0.0280(14) -0.0098(16) C4 0.090(2) 0.0610(18) 0.113(2) -0.0206(15) -0.0451(17) -0.0060(16) C5 0.0860(18) 0.0501(15) 0.0708(15) -0.0006(12) -0.0410(13) -0.0158(13) C6 0.0735(15) 0.0498(14) 0.0510(12) 0.0083(10) -0.0341(11) -0.0227(12) C7 0.1004(19) 0.0714(18) 0.0693(15) 0.0151(13) -0.0356(13) -0.0508(16) C8 0.132(3) 0.0663(19) 0.0811(17) 0.0173(14) -0.0541(18) -0.0575(19) C9 0.125(3) 0.0475(16) 0.0861(18) 0.0051(13) -0.0561(18) -0.0299(16) C10 0.0590(13) 0.0532(14) 0.0710(14) 0.0009(11) -0.0191(10) -0.0273(12) C11 0.0671(14) 0.0495(14) 0.0550(12) -0.0024(10) -0.0179(10) -0.0282(12) C12 0.0678(15) 0.0553(15) 0.0582(13) -0.0036(11) 0.0000(11) -0.0219(13) C13 0.0627(16) 0.083(2) 0.0739(16) 0.0011(14) -0.0105(13) -0.0229(15) C14 0.072(2) 0.102(3) 0.118(3) 0.005(2) -0.0133(17) -0.013(2) C15 0.088(3) 0.087(3) 0.147(3) -0.009(3) 0.009(2) -0.004(2) C16 0.110(3) 0.080(2) 0.114(3) -0.0307(19) 0.017(2) -0.025(2) C17 0.094(2) 0.0686(19) 0.0700(16) -0.0151(14) 0.0043(14) -0.0328(17) C18 0.148(3) 0.111(3) 0.0756(18) -0.0204(17) -0.0228(19) -0.059(2) C19 0.0871(19) 0.122(3) 0.093(2) -0.0062(18) -0.0325(15) -0.0424(19) C20 0.0545(13) 0.0734(16) 0.0523(12) 0.0055(11) -0.0219(10) -0.0209(12) C21 0.0720(15) 0.097(2) 0.0582(14) 0.0177(13) -0.0201(12) -0.0300(14) C22 0.093(2) 0.120(2) 0.0575(15) 0.0219(15) -0.0365(14) -0.0272(18) C23 0.0812(19) 0.129(3) 0.0736(18) 0.0019(17) -0.0437(15) -0.0255(18) C24 0.0635(15) 0.0876(18) 0.0655(15) -0.0053(13) -0.0307(12) -0.0199(13) C25 0.0510(12) 0.0669(15) 0.0544(12) -0.0019(11) -0.0195(10) -0.0193(11) C26 0.0771(17) 0.107(2) 0.0885(18) 0.0160(15) -0.0287(14) -0.0562(17) C27 0.0823(19) 0.128(3) 0.109(2) 0.008(2) -0.0379(17) -0.0638(19) C28 0.0718(17) 0.126(3) 0.102(2) -0.0127(19) -0.0434(15) -0.0418(17) C29 0.0638(15) 0.113(2) 0.0791(16) 0.0276(15) -0.0262(13) -0.0518(15) C30 0.0556(14) 0.0920(19) 0.0701(15) 0.0085(13) -0.0197(11) -0.0399(14) C31 0.0502(12) 0.0809(18) 0.0629(13) 0.0039(12) -0.0216(10) -0.0278(12) C32 0.110(2) 0.079(2) 0.114(2) -0.0006(19) -0.044(2) -0.0210(19) C33 0.128(3) 0.099(3) 0.169(4) 0.031(3) -0.044(3) -0.006(2) C34 0.098(3) 0.211(6) 0.135(4) 0.056(4) -0.070(3) -0.049(3) C35 0.114(3) 0.225(5) 0.105(3) 0.023(4) -0.066(3) -0.083(4) C36 0.0821(18) 0.125(3) 0.0746(17) -0.0012(17) -0.0287(14) -0.0496(19) C37 0.213(5) 0.145(4) 0.153(4) -0.061(3) -0.058(3) -0.058(4) C38 0.287(6) 0.105(3) 0.205(5) -0.049(3) -0.108(4) -0.046(4) N1 0.0790(13) 0.0591(12) 0.0577(10) 0.0111(9) -0.0287(9) -0.0348(11) N2 0.0660(13) 0.0495(12) 0.0601(11) 0.0005(9) -0.0115(9) -0.0260(10) N3 0.0611(11) 0.0840(14) 0.0652(12) 0.0118(10) -0.0247(9) -0.0373(11) N4 0.0473(11) 0.0849(15) 0.0676(12) 0.0090(10) -0.0198(9) -0.0314(10) O1 0.0642(9) 0.0483(9) 0.0686(9) -0.0007(7) -0.0124(7) -0.0268(8) O2 0.0856(11) 0.0527(10) 0.0840(11) -0.0043(8) -0.0108(8) -0.0389(9) O3 0.0586(9) 0.1069(13) 0.0590(9) 0.0220(8) -0.0246(7) -0.0469(9) O4 0.0630(11) 0.1496(18) 0.0987(13) 0.0295(12) -0.0252(9) -0.0630(12) O5 0.0609(10) 0.0782(13) 0.0560(9) 0.0049(9) -0.0149(8) -0.0342(9) _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 1.365(3) . ? C1 O1 1.366(2) . ? C1 C6 1.429(3) . ? C2 C3 1.407(3) . ? C2 H2 0.9300 . ? C3 C4 1.350(4) . ? C3 H3 0.9300 . ? C4 C5 1.403(4) . ? C4 H4 0.9300 . ? C5 C9 1.407(3) . ? C5 C6 1.412(3) . ? C6 N1 1.363(3) . ? C7 N1 1.320(3) . ? C7 C8 1.394(4) . ? C7 H7 0.9300 . ? C8 C9 1.340(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O1 1.417(2) . ? C10 C11 1.491(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.229(2) . ? C11 N2 1.337(3) . ? C12 C13 1.387(3) . ? C12 C17 1.394(3) . ? C12 N2 1.439(3) . ? C13 C14 1.386(4) . ? C13 C19 1.498(4) . ? C14 C15 1.370(5) . ? C14 H14 0.9300 . ? C15 C16 1.366(5) . ? C15 H15 0.9300 . ? C16 C17 1.398(4) . ? C16 H16 0.9300 . ? C17 C18 1.506(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.358(3) . ? C20 O3 1.374(2) . ? C20 C25 1.416(3) . ? C21 C22 1.404(4) . ? C21 H21 0.9300 . ? C22 C23 1.341(4) . ? C22 H22 0.9300 . ? C23 C24 1.402(4) . ? C23 H23 0.9300 . ? C24 C28 1.409(3) . ? C24 C25 1.416(3) . ? C25 N3 1.362(3) . ? C26 N3 1.316(3) . ? C26 C27 1.393(4) . ? C26 H26 0.9300 . ? C27 C28 1.340(4) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 O3 1.423(2) . ? C29 C30 1.500(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 O4 1.224(2) . ? C30 N4 1.334(3) . ? C31 C32 1.364(4) . ? C31 C36 1.388(3) . ? C31 N4 1.425(3) . ? C32 C33 1.430(6) . ? C32 C38 1.509(5) . ? C33 C34 1.364(6) . ? C33 H33 0.9300 . ? C34 C35 1.303(6) . ? C34 H34 0.9300 . ? C35 C36 1.361(5) . ? C35 H35 0.9300 . ? C36 C37 1.519(5) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? N2 H2N 0.90(2) . ? N4 H4N 0.88(3) . ? O5 H1S 0.91(4) . ? O5 H2S 0.92(4) . ? 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 O1 124.94(19) . . ? C2 C1 C6 120.1(2) . . ? O1 C1 C6 114.99(18) . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C9 C5 C4 123.6(3) . . ? C9 C5 C6 117.0(2) . . ? C4 C5 C6 119.3(2) . . ? N1 C6 C5 122.2(2) . . ? N1 C6 C1 119.0(2) . . ? C5 C6 C1 118.7(2) . . ? N1 C7 C8 124.3(3) . . ? N1 C7 H7 117.9 . . ? C8 C7 H7 117.9 . . ? C9 C8 C7 118.7(2) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 C5 120.5(3) . . ? C8 C9 H9 119.8 . . ? C5 C9 H9 119.8 . . ? O1 C10 C11 112.60(17) . . ? O1 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? O1 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? O2 C11 N2 123.9(2) . . ? O2 C11 C10 117.62(19) . . ? N2 C11 C10 118.43(18) . . ? C13 C12 C17 122.3(3) . . ? C13 C12 N2 118.0(2) . . ? C17 C12 N2 119.7(2) . . ? C14 C13 C12 117.9(3) . . ? C14 C13 C19 120.9(3) . . ? C12 C13 C19 121.2(2) . . ? C15 C14 C13 120.8(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 120.8(4) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C17 120.8(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 117.3(3) . . ? C12 C17 C18 122.0(3) . . ? C16 C17 C18 120.8(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 . . ? C13 C19 H19A 109.5 . . ? C13 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C13 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 O3 124.6(2) . . ? C21 C20 C25 120.5(2) . . ? O3 C20 C25 114.90(18) . . ? C20 C21 C22 119.7(2) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C23 C22 C21 121.4(2) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C28 123.8(2) . . ? C23 C24 C25 119.1(2) . . ? C28 C24 C25 117.1(2) . . ? N3 C25 C24 121.83(19) . . ? N3 C25 C20 119.57(18) . . ? C24 C25 C20 118.6(2) . . ? N3 C26 C27 124.8(3) . . ? N3 C26 H26 117.6 . . ? C27 C26 H26 117.6 . . ? C28 C27 C26 118.1(2) . . ? C28 C27 H27 120.9 . . ? C26 C27 H27 120.9 . . ? C27 C28 C24 120.7(2) . . ? C27 C28 H28 119.7 . . ? C24 C28 H28 119.7 . . ? O3 C29 C30 111.84(18) . . ? O3 C29 H29A 109.2 . . ? C30 C29 H29A 109.2 . . ? O3 C29 H29B 109.2 . . ? C30 C29 H29B 109.2 . . ? H29A C29 H29B 107.9 . . ? O4 C30 N4 124.2(2) . . ? O4 C30 C29 117.7(2) . . ? N4 C30 C29 118.10(19) . . ? C32 C31 C36 121.5(3) . . ? C32 C31 N4 119.8(2) . . ? C36 C31 N4 118.6(2) . . ? C31 C32 C33 116.3(3) . . ? C31 C32 C38 120.6(3) . . ? C33 C32 C38 123.1(4) . . ? C34 C33 C32 120.5(4) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C35 C34 C33 120.5(5) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 122.5(5) . . ? C34 C35 H35 118.8 . . ? C36 C35 H35 118.8 . . ? C35 C36 C31 118.6(4) . . ? C35 C36 C37 121.2(4) . . ? C31 C36 C37 120.2(3) . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C32 C38 H38A 109.5 . . ? C32 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C32 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C7 N1 C6 117.3(2) . . ? C11 N2 C12 122.44(18) . . ? C11 N2 H2N 119.1(14) . . ? C12 N2 H2N 118.4(14) . . ? C26 N3 C25 117.45(19) . . ? C30 N4 C31 123.57(19) . . ? C30 N4 H4N 118.1(16) . . ? C31 N4 H4N 118.3(16) . . ? C1 O1 C10 117.28(16) . . ? C20 O3 C29 117.17(16) . . ? H1S O5 H2S 110(3) . . ? 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 O1 C1 C2 C3 -177.8(2) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C3 C4 C5 C9 177.9(2) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C9 C5 C6 N1 2.2(3) . . . . ? C4 C5 C6 N1 -179.1(2) . . . . ? C9 C5 C6 C1 -176.74(19) . . . . ? C4 C5 C6 C1 2.0(3) . . . . ? C2 C1 C6 N1 179.0(2) . . . . ? O1 C1 C6 N1 -2.3(3) . . . . ? C2 C1 C6 C5 -2.1(3) . . . . ? O1 C1 C6 C5 176.67(17) . . . . ? N1 C7 C8 C9 2.3(4) . . . . ? C7 C8 C9 C5 -1.7(4) . . . . ? C4 C5 C9 C8 -179.1(3) . . . . ? C6 C5 C9 C8 -0.4(3) . . . . ? O1 C10 C11 O2 -173.87(18) . . . . ? O1 C10 C11 N2 5.6(3) . . . . ? C17 C12 C13 C14 3.8(3) . . . . ? N2 C12 C13 C14 -176.6(2) . . . . ? C17 C12 C13 C19 -176.0(2) . . . . ? N2 C12 C13 C19 3.6(3) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C19 C13 C14 C15 179.8(3) . . . . ? C13 C14 C15 C16 -2.3(5) . . . . ? C14 C15 C16 C17 0.9(5) . . . . ? C13 C12 C17 C16 -5.1(3) . . . . ? N2 C12 C17 C16 175.3(2) . . . . ? C13 C12 C17 C18 173.0(2) . . . . ? N2 C12 C17 C18 -6.6(3) . . . . ? C15 C16 C17 C12 2.7(4) . . . . ? C15 C16 C17 C18 -175.4(3) . . . . ? O3 C20 C21 C22 -177.8(2) . . . . ? C25 C20 C21 C22 1.7(4) . . . . ? C20 C21 C22 C23 -0.7(4) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C22 C23 C24 C28 -178.9(3) . . . . ? C22 C23 C24 C25 0.2(4) . . . . ? C23 C24 C25 N3 -179.0(2) . . . . ? C28 C24 C25 N3 0.2(3) . . . . ? C23 C24 C25 C20 0.7(3) . . . . ? C28 C24 C25 C20 179.9(2) . . . . ? C21 C20 C25 N3 178.0(2) . . . . ? O3 C20 C25 N3 -2.5(3) . . . . ? C21 C20 C25 C24 -1.7(3) . . . . ? O3 C20 C25 C24 177.8(2) . . . . ? N3 C26 C27 C28 0.4(5) . . . . ? C26 C27 C28 C24 -0.6(5) . . . . ? C23 C24 C28 C27 179.4(3) . . . . ? C25 C24 C28 C27 0.3(4) . . . . ? O3 C29 C30 O4 -173.8(2) . . . . ? O3 C29 C30 N4 5.2(3) . . . . ? C36 C31 C32 C33 2.0(4) . . . . ? N4 C31 C32 C33 179.0(3) . . . . ? C36 C31 C32 C38 -178.1(3) . . . . ? N4 C31 C32 C38 -1.0(5) . . . . ? C31 C32 C33 C34 -1.7(6) . . . . ? C38 C32 C33 C34 178.4(4) . . . . ? C32 C33 C34 C35 -1.3(7) . . . . ? C33 C34 C35 C36 4.1(7) . . . . ? C34 C35 C36 C31 -3.8(6) . . . . ? C34 C35 C36 C37 175.3(4) . . . . ? C32 C31 C36 C35 0.6(4) . . . . ? N4 C31 C36 C35 -176.5(3) . . . . ? C32 C31 C36 C37 -178.5(3) . . . . ? N4 C31 C36 C37 4.4(4) . . . . ? C8 C7 N1 C6 -0.6(3) . . . . ? C5 C6 N1 C7 -1.6(3) . . . . ? C1 C6 N1 C7 177.25(18) . . . . ? O2 C11 N2 C12 9.3(3) . . . . ? C10 C11 N2 C12 -170.1(2) . . . . ? C13 C12 N2 C11 109.1(2) . . . . ? C17 C12 N2 C11 -71.3(3) . . . . ? C27 C26 N3 C25 0.1(4) . . . . ? C24 C25 N3 C26 -0.4(3) . . . . ? C20 C25 N3 C26 179.9(2) . . . . ? O4 C30 N4 C31 3.7(4) . . . . ? C29 C30 N4 C31 -175.3(2) . . . . ? C32 C31 N4 C30 96.9(3) . . . . ? C36 C31 N4 C30 -85.9(3) . . . . ? C2 C1 O1 C10 7.5(3) . . . . ? C6 C1 O1 C10 -171.16(17) . . . . ? C11 C10 O1 C1 170.56(17) . . . . ? C21 C20 O3 C29 10.0(3) . . . . ? C25 C20 O3 C29 -169.5(2) . . . . ? C30 C29 O3 C20 160.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 0.155 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.027 # Attachment 'dmahq.cif' data_dmahq _database_code_depnum_ccdc_archive 'CCDC 625306' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H42 N4 O6' _chemical_formula_weight 722.82 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.528(2) _cell_length_b 11.516(3) _cell_length_c 12.334(3) _cell_angle_alpha 114.290(4) _cell_angle_beta 99.137(4) _cell_angle_gamma 96.136(4) _cell_volume 944.4(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 382 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 8512 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 7.61 _diffrn_reflns_theta_max 28.25 _reflns_number_total 4332 _reflns_number_gt 2845 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^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_number_reflns 4332 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1604 _refine_ls_wR_factor_gt 0.1360 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 C1 C 0.3093(2) 0.96285(15) 0.79988(15) 0.0578(4) Uani 1 1 d . . . H1 H 0.3292 0.9340 0.7213 0.069 Uiso 1 1 calc R . . C2 C 0.3056(3) 1.09456(15) 0.86397(19) 0.0650(5) Uani 1 1 d . . . H2 H 0.3242 1.1514 0.8290 0.078 Uiso 1 1 calc R . . C3 C 0.2747(2) 1.13718(14) 0.97649(18) 0.0629(5) Uani 1 1 d . . . H3 H 0.2704 1.2243 1.0200 0.075 Uiso 1 1 calc R . . C4 C 0.2488(2) 1.05089(13) 1.02955(15) 0.0518(4) Uani 1 1 d . . . C5 C 0.25724(18) 0.91926(12) 0.95874(12) 0.0438(3) Uani 1 1 d . . . C6 C 0.2173(2) 1.08908(15) 1.14757(16) 0.0651(5) Uani 1 1 d . . . H6 H 0.2122 1.1753 1.1946 0.078 Uiso 1 1 calc R . . C7 C 0.1944(3) 1.00181(18) 1.19289(16) 0.0674(5) Uani 1 1 d . . . H7 H 0.1710 1.0283 1.2705 0.081 Uiso 1 1 calc R . . C8 C 0.2052(2) 0.87052(16) 1.12487(14) 0.0592(4) Uani 1 1 d . . . H8 H 0.1909 0.8119 1.1583 0.071 Uiso 1 1 calc R . . C9 C 0.2367(2) 0.82983(12) 1.00999(13) 0.0466(3) Uani 1 1 d . . . C10 C 0.2484(3) 0.61646(14) 0.98924(15) 0.0591(4) Uani 1 1 d . . . H10A H 0.1285 0.6023 1.0062 0.071 Uiso 1 1 calc R . . H10B H 0.3386 0.6526 1.0659 0.071 Uiso 1 1 calc R . . C11 C 0.2879(3) 0.48843(14) 0.90456(15) 0.0572(4) Uani 1 1 d . . . C12 C 0.3744(2) 0.36887(13) 0.71104(13) 0.0492(4) Uani 1 1 d . . . C13 C 0.2456(2) 0.25324(15) 0.64767(15) 0.0597(4) Uani 1 1 d . . . C14 C 0.2975(3) 0.15085(17) 0.55700(18) 0.0783(6) Uani 1 1 d . . . H14 H 0.2170 0.0713 0.5158 0.094 Uiso 1 1 calc R . . C15 C 0.4623(4) 0.16402(19) 0.5272(2) 0.0852(6) Uani 1 1 d . . . H15 H 0.4915 0.0948 0.4646 0.102 Uiso 1 1 calc R . . C16 C 0.5855(3) 0.2790(2) 0.58912(18) 0.0734(5) Uani 1 1 d . . . H16 H 0.6976 0.2873 0.5677 0.088 Uiso 1 1 calc R . . C17 C 0.5454(2) 0.38317(15) 0.68335(14) 0.0564(4) Uani 1 1 d . . . C18 C 0.6815(3) 0.50893(19) 0.75195(18) 0.0736(5) Uani 1 1 d . . . H18A H 0.7964 0.4976 0.7284 0.110 Uiso 1 1 calc R . . H18B H 0.6988 0.5346 0.8380 0.110 Uiso 1 1 calc R . . H18C H 0.6362 0.5749 0.7332 0.110 Uiso 1 1 calc R . . C19 C 0.0586(3) 0.2405(2) 0.6708(2) 0.0881(6) Uani 1 1 d . . . H19A H 0.0651 0.2371 0.7478 0.132 Uiso 1 1 calc R . . H19B H -0.0173 0.1623 0.6069 0.132 Uiso 1 1 calc R . . H19C H 0.0071 0.3139 0.6727 0.132 Uiso 1 1 calc R . . C21 C 0.1608(3) 0.45342(15) 0.49675(14) 0.0608(4) Uani 1 1 d . . . H21 H 0.2692 0.4215 0.4942 0.073 Uiso 1 1 calc R . . C22 C 0.1584(2) 0.57460(14) 0.58747(12) 0.0509(4) Uani 1 1 d . . . C23 C -0.0030(3) 0.61981(14) 0.58951(14) 0.0590(4) Uani 1 1 d . . . H23 H -0.0061 0.7009 0.6499 0.071 Uiso 1 1 calc R . . H2N H 0.337(3) 0.548(2) 0.7867(18) 0.072(6) Uiso 1 1 d . . . H3O H 0.304(3) 0.717(3) 0.733(2) 0.087(6) Uiso 1 1 d . . . N1 N 0.28650(17) 0.87709(11) 0.84391(11) 0.0478(3) Uani 1 1 d . . . N2 N 0.3270(2) 0.47972(12) 0.80023(11) 0.0523(3) Uani 1 1 d . . . O1 O 0.25293(16) 0.70594(9) 0.93767(9) 0.0545(3) Uani 1 1 d . . . O2 O 0.2827(2) 0.40073(11) 0.93598(12) 0.0830(5) Uani 1 1 d . . . O3 O 0.31915(17) 0.64332(11) 0.67208(10) 0.0607(3) 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 0.0642(10) 0.0504(8) 0.0606(9) 0.0289(7) 0.0085(7) 0.0065(7) C2 0.0670(11) 0.0468(8) 0.0846(12) 0.0378(8) 0.0045(9) 0.0050(7) C3 0.0590(10) 0.0359(7) 0.0851(12) 0.0215(7) 0.0072(8) 0.0072(6) C4 0.0433(8) 0.0370(6) 0.0627(9) 0.0121(6) 0.0063(6) 0.0060(5) C5 0.0397(7) 0.0355(6) 0.0493(7) 0.0137(5) 0.0062(5) 0.0053(5) C6 0.0656(11) 0.0432(7) 0.0663(10) 0.0038(7) 0.0175(8) 0.0095(7) C7 0.0701(11) 0.0628(10) 0.0545(9) 0.0078(8) 0.0241(8) 0.0120(8) C8 0.0676(10) 0.0562(8) 0.0534(8) 0.0200(7) 0.0235(7) 0.0116(7) C9 0.0493(8) 0.0383(6) 0.0477(7) 0.0137(5) 0.0126(6) 0.0082(5) C10 0.0861(12) 0.0457(7) 0.0575(8) 0.0293(7) 0.0272(8) 0.0151(7) C11 0.0797(11) 0.0412(7) 0.0568(8) 0.0265(6) 0.0179(8) 0.0116(7) C12 0.0616(10) 0.0405(6) 0.0474(7) 0.0210(6) 0.0093(6) 0.0143(6) C13 0.0670(11) 0.0472(8) 0.0582(8) 0.0211(7) 0.0051(7) 0.0055(7) C14 0.1045(16) 0.0460(8) 0.0648(10) 0.0102(7) 0.0115(10) 0.0047(9) C15 0.1126(18) 0.0613(10) 0.0733(12) 0.0141(9) 0.0308(12) 0.0322(11) C16 0.0762(12) 0.0762(11) 0.0687(11) 0.0260(9) 0.0245(9) 0.0292(9) C17 0.0623(10) 0.0541(8) 0.0545(8) 0.0255(7) 0.0114(7) 0.0140(7) C18 0.0722(12) 0.0698(11) 0.0722(11) 0.0278(9) 0.0167(9) -0.0001(9) C19 0.0684(13) 0.0768(12) 0.1008(15) 0.0284(11) 0.0104(11) -0.0036(9) C21 0.0744(11) 0.0568(9) 0.0512(8) 0.0195(7) 0.0170(8) 0.0253(8) C22 0.0743(10) 0.0455(7) 0.0381(7) 0.0219(6) 0.0150(6) 0.0140(7) C23 0.0836(12) 0.0455(7) 0.0463(8) 0.0158(6) 0.0162(7) 0.0219(7) N1 0.0539(7) 0.0401(5) 0.0478(6) 0.0193(5) 0.0078(5) 0.0069(5) N2 0.0746(9) 0.0366(6) 0.0534(7) 0.0239(5) 0.0194(6) 0.0157(5) O1 0.0831(8) 0.0369(5) 0.0512(5) 0.0217(4) 0.0258(5) 0.0162(5) O2 0.1465(13) 0.0466(6) 0.0711(8) 0.0365(6) 0.0339(8) 0.0205(7) O3 0.0755(8) 0.0500(6) 0.0520(6) 0.0186(5) 0.0110(5) 0.0142(5) _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 1.317(2) . ? C1 C2 1.399(2) . ? C1 H1 0.9300 . ? C2 C3 1.337(3) . ? C2 H2 0.9300 . ? C3 C4 1.410(2) . ? C3 H3 0.9300 . ? C4 C6 1.405(3) . ? C4 C5 1.4192(18) . ? C5 N1 1.3588(19) . ? C5 C9 1.420(2) . ? C6 C7 1.345(3) . ? C6 H6 0.9300 . ? C7 C8 1.415(2) . ? C7 H7 0.9300 . ? C8 C9 1.367(2) . ? C8 H8 0.9300 . ? C9 O1 1.3678(16) . ? C10 O1 1.4164(18) . ? C10 C11 1.509(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.2207(19) . ? C11 N2 1.332(2) . ? C12 C17 1.393(3) . ? C12 C13 1.397(2) . ? C12 N2 1.4260(19) . ? C13 C14 1.395(3) . ? C13 C19 1.484(3) . ? C14 C15 1.360(3) . ? C14 H14 0.9300 . ? C15 C16 1.370(3) . ? C15 H15 0.9300 . ? C16 C17 1.387(3) . ? C16 H16 0.9300 . ? C17 C18 1.504(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 C23 1.378(2) 2_566 ? C21 C22 1.388(2) . ? C21 H21 0.9300 . ? C22 C23 1.372(2) . ? C22 O3 1.376(2) . ? C23 C21 1.378(2) 2_566 ? C23 H23 0.9300 . ? N2 H2N 0.87(2) . ? O3 H3O 0.90(3) . ? 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 C2 124.10(16) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C1 118.67(16) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 120.41(14) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C6 C4 C3 123.47(14) . . ? C6 C4 C5 119.33(15) . . ? C3 C4 C5 117.20(15) . . ? N1 C5 C4 121.70(13) . . ? N1 C5 C9 119.28(11) . . ? C4 C5 C9 119.01(14) . . ? C7 C6 C4 120.42(14) . . ? C7 C6 H6 119.8 . . ? C4 C6 H6 119.8 . . ? C6 C7 C8 121.29(16) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 119.98(17) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 O1 124.59(14) . . ? C8 C9 C5 119.93(13) . . ? O1 C9 C5 115.47(12) . . ? O1 C10 C11 111.39(13) . . ? O1 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? O1 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O2 C11 N2 124.56(14) . . ? O2 C11 C10 118.35(15) . . ? N2 C11 C10 117.08(13) . . ? C17 C12 C13 121.86(14) . . ? C17 C12 N2 118.02(13) . . ? C13 C12 N2 119.94(15) . . ? C14 C13 C12 116.96(18) . . ? C14 C13 C19 120.94(17) . . ? C12 C13 C19 122.04(16) . . ? C15 C14 C13 121.88(17) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 120.18(17) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 120.9(2) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C12 118.17(16) . . ? C16 C17 C18 120.81(18) . . ? C12 C17 C18 121.01(15) . . ? 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 . . ? C13 C19 H19A 109.5 . . ? C13 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C13 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C23 C21 C22 120.24(16) 2_566 . ? C23 C21 H21 119.9 2_566 . ? C22 C21 H21 119.9 . . ? C23 C22 O3 123.12(13) . . ? C23 C22 C21 118.91(15) . . ? O3 C22 C21 117.97(15) . . ? C22 C23 C21 120.85(14) . 2_566 ? C22 C23 H23 119.6 . . ? C21 C23 H23 119.6 2_566 . ? C1 N1 C5 117.92(12) . . ? C11 N2 C12 125.25(13) . . ? C11 N2 H2N 119.2(14) . . ? C12 N2 H2N 115.2(14) . . ? C9 O1 C10 117.17(12) . . ? C22 O3 H3O 112.7(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 N1 C1 C2 C3 -0.9(3) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C6 179.47(17) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C6 C4 C5 N1 179.69(14) . . . . ? C3 C4 C5 N1 -0.9(2) . . . . ? C6 C4 C5 C9 -1.1(2) . . . . ? C3 C4 C5 C9 178.32(13) . . . . ? C3 C4 C6 C7 -179.70(16) . . . . ? C5 C4 C6 C7 -0.4(2) . . . . ? C4 C6 C7 C8 1.4(3) . . . . ? C6 C7 C8 C9 -1.0(3) . . . . ? C7 C8 C9 O1 178.75(15) . . . . ? C7 C8 C9 C5 -0.5(2) . . . . ? N1 C5 C9 C8 -179.28(14) . . . . ? C4 C5 C9 C8 1.5(2) . . . . ? N1 C5 C9 O1 1.45(19) . . . . ? C4 C5 C9 O1 -177.82(12) . . . . ? O1 C10 C11 O2 -177.74(16) . . . . ? O1 C10 C11 N2 2.6(2) . . . . ? C17 C12 C13 C14 1.6(3) . . . . ? N2 C12 C13 C14 176.54(16) . . . . ? C17 C12 C13 C19 -175.58(19) . . . . ? N2 C12 C13 C19 -0.7(3) . . . . ? C12 C13 C14 C15 -3.0(3) . . . . ? C19 C13 C14 C15 174.3(2) . . . . ? C13 C14 C15 C16 2.0(4) . . . . ? C14 C15 C16 C17 0.5(3) . . . . ? C15 C16 C17 C12 -1.7(3) . . . . ? C15 C16 C17 C18 179.5(2) . . . . ? C13 C12 C17 C16 0.6(2) . . . . ? N2 C12 C17 C16 -174.36(15) . . . . ? C13 C12 C17 C18 179.43(16) . . . . ? N2 C12 C17 C18 4.4(2) . . . . ? C23 C21 C22 C23 -0.1(3) 2_566 . . . ? C23 C21 C22 O3 179.40(15) 2_566 . . . ? O3 C22 C23 C21 -179.38(15) . . . 2_566 ? C21 C22 C23 C21 0.1(3) . . . 2_566 ? C2 C1 N1 C5 0.1(2) . . . . ? C4 C5 N1 C1 0.8(2) . . . . ? C9 C5 N1 C1 -178.42(13) . . . . ? O2 C11 N2 C12 -2.1(3) . . . . ? C10 C11 N2 C12 177.60(16) . . . . ? C17 C12 N2 C11 -119.57(18) . . . . ? C13 C12 N2 C11 65.3(2) . . . . ? C8 C9 O1 C10 -4.3(2) . . . . ? C5 C9 O1 C10 174.94(13) . . . . ? C11 C10 O1 C9 -173.91(13) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.173 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.025 # Attachment 'dmand_0m.cif' data_dmand_0m _database_code_depnum_ccdc_archive 'CCDC 625307' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N2 O3' _chemical_formula_weight 386.44 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 8.1869(2) _cell_length_b 10.4020(2) _cell_length_c 13.6322(3) _cell_angle_alpha 111.239(2) _cell_angle_beta 93.668(2) _cell_angle_gamma 105.441(2) _cell_volume 1026.25(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1912 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 28.23 _exptl_crystal_description plates _exptl_crystal_colour red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.083 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5472 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3430 _reflns_number_gt 2684 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0536P)^2^+0.2541P] 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_number_reflns 3430 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.0560(2) 0.4624(2) 0.19638(17) 0.0629(5) Uani 1 1 d . . . H1 H 0.0440 0.5088 0.2668 0.075 Uiso 1 1 calc R . . C2 C -0.0382(2) 0.3153(2) 0.1420(2) 0.0646(6) Uani 1 1 d . . . H2 H -0.1107 0.2660 0.1754 0.078 Uiso 1 1 calc R . . C3 C -0.0212(2) 0.24733(18) 0.04056(19) 0.0601(6) Uani 1 1 d . . . H3 H -0.0822 0.1495 0.0033 0.072 Uiso 1 1 calc R . . C4 C 0.0879(2) 0.32261(16) -0.01024(16) 0.0487(5) Uani 1 1 d . . . C5 C 0.17847(19) 0.47191(16) 0.05151(15) 0.0428(4) Uani 1 1 d . . . C6 C 0.1097(2) 0.25904(19) -0.11614(18) 0.0627(6) Uani 1 1 d . . . H6 H 0.0494 0.1620 -0.1571 0.075 Uiso 1 1 calc R . . C7 C 0.2176(3) 0.3374(2) -0.15949(18) 0.0668(6) Uani 1 1 d . . . H7 H 0.2318 0.2933 -0.2297 0.080 Uiso 1 1 calc R . . C8 C 0.3093(2) 0.48593(19) -0.09933(16) 0.0570(5) Uani 1 1 d . . . H8 H 0.3833 0.5382 -0.1303 0.068 Uiso 1 1 calc R . . C9 C 0.2898(2) 0.55236(16) 0.00305(14) 0.0437(4) Uani 1 1 d . . . C10 C 0.4847(2) 0.77834(17) 0.02234(14) 0.0472(4) Uani 1 1 d . . . H10A H 0.4221 0.7770 -0.0411 0.057 Uiso 1 1 calc R . . H10B H 0.5738 0.7339 0.0008 0.057 Uiso 1 1 calc R . . C11 C 0.5674(2) 0.93381(17) 0.10055(15) 0.0467(4) Uani 1 1 d . . . C12 C 0.5736(2) 1.12854(17) 0.26810(15) 0.0493(4) Uani 1 1 d . . . C13 C 0.7314(2) 1.17649(18) 0.33533(16) 0.0564(5) Uani 1 1 d . . . C14 C 0.7884(3) 1.3200(2) 0.40879(19) 0.0763(7) Uani 1 1 d . . . H14 H 0.8936 1.3546 0.4546 0.092 Uiso 1 1 calc R . . C15 C 0.6923(4) 1.4111(2) 0.4148(2) 0.0892(8) Uani 1 1 d . . . H15 H 0.7327 1.5067 0.4643 0.107 Uiso 1 1 calc R . . C16 C 0.5363(4) 1.3620(2) 0.3479(2) 0.0820(7) Uani 1 1 d . . . H16 H 0.4724 1.4251 0.3523 0.098 Uiso 1 1 calc R . . C17 C 0.4728(3) 1.2186(2) 0.27332(17) 0.0605(5) Uani 1 1 d . . . C18 C 0.2998(3) 1.1632(3) 0.2034(2) 0.0865(7) Uani 1 1 d . . . H18A H 0.2217 1.0948 0.2242 0.130 Uiso 1 1 calc R . . H18B H 0.3102 1.1163 0.1302 0.130 Uiso 1 1 calc R . . H18C H 0.2565 1.2428 0.2110 0.130 Uiso 1 1 calc R . . C19 C 0.8374(3) 1.0788(2) 0.3314(2) 0.0766(7) Uani 1 1 d . . . H19A H 0.7657 0.9887 0.3306 0.115 Uiso 1 1 calc R . . H19B H 0.9272 1.1243 0.3933 0.115 Uiso 1 1 calc R . . H19C H 0.8875 1.0606 0.2679 0.115 Uiso 1 1 calc R . . C20 C 0.4840(3) 0.7543(2) 0.36385(17) 0.0628(5) Uani 1 1 d . . . H20 H 0.4565 0.6661 0.3053 0.075 Uiso 1 1 calc R . . C21 C 0.3913(2) 0.84633(18) 0.36966(14) 0.0495(4) Uani 1 1 d . . . C22 C 0.4301(2) 0.98156(18) 0.45890(14) 0.0483(4) Uani 1 1 d . . . C23 C 0.3342(3) 1.0782(2) 0.46739(16) 0.0579(5) Uani 1 1 d . . . H23 H 0.2410 1.0538 0.4142 0.070 Uiso 1 1 calc R . . C24 C 0.3777(3) 1.2073(2) 0.55325(18) 0.0693(6) Uani 1 1 d . . . H24 H 0.3152 1.2712 0.5573 0.083 Uiso 1 1 calc R . . H2N H 0.425(2) 0.923(2) 0.2032(15) 0.058(5) Uiso 1 1 d . . . H3O H 0.232(3) 0.719(3) 0.239(2) 0.107(9) Uiso 1 1 d . . . N1 N 0.16047(18) 0.53911(15) 0.15398(12) 0.0506(4) Uani 1 1 d . . . N2 N 0.50916(19) 0.98015(15) 0.19147(13) 0.0509(4) Uani 1 1 d . . . O1 O 0.36951(14) 0.69597(11) 0.06776(9) 0.0481(3) Uani 1 1 d . . . O2 O 0.68300(17) 1.01016(13) 0.07456(11) 0.0690(4) Uani 1 1 d . . . O3 O 0.26046(17) 0.81937(14) 0.29053(11) 0.0602(4) 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 0.0601(11) 0.0559(11) 0.0613(14) 0.0245(10) 0.0093(9) -0.0013(9) C2 0.0541(11) 0.0515(11) 0.0829(17) 0.0342(12) 0.0074(10) -0.0017(8) C3 0.0470(10) 0.0322(8) 0.0891(18) 0.0233(10) -0.0025(9) -0.0023(7) C4 0.0413(8) 0.0298(7) 0.0626(14) 0.0097(8) -0.0028(8) 0.0065(6) C5 0.0376(8) 0.0309(7) 0.0523(12) 0.0138(8) -0.0018(7) 0.0049(6) C6 0.0576(11) 0.0323(8) 0.0738(16) 0.0019(10) -0.0006(10) 0.0047(8) C7 0.0720(13) 0.0488(10) 0.0555(14) -0.0026(10) 0.0084(10) 0.0142(9) C8 0.0599(11) 0.0438(9) 0.0531(14) 0.0102(9) 0.0093(9) 0.0062(8) C9 0.0437(8) 0.0300(7) 0.0454(12) 0.0077(8) -0.0001(7) 0.0045(6) C10 0.0478(9) 0.0374(8) 0.0473(11) 0.0148(8) 0.0091(7) 0.0016(7) C11 0.0484(9) 0.0362(8) 0.0483(12) 0.0170(8) 0.0064(8) 0.0021(7) C12 0.0571(10) 0.0323(8) 0.0507(11) 0.0137(8) 0.0149(8) 0.0042(7) C13 0.0581(10) 0.0405(9) 0.0605(13) 0.0152(9) 0.0111(9) 0.0056(8) C14 0.0765(14) 0.0484(11) 0.0743(17) 0.0057(11) -0.0003(11) 0.0014(10) C15 0.110(2) 0.0400(11) 0.0879(19) 0.0013(11) 0.0099(15) 0.0121(12) C16 0.1090(19) 0.0514(11) 0.0902(19) 0.0225(12) 0.0279(15) 0.0376(12) C17 0.0711(12) 0.0513(10) 0.0609(14) 0.0229(10) 0.0184(10) 0.0194(9) C18 0.0825(16) 0.0957(18) 0.0894(19) 0.0362(15) 0.0154(14) 0.0410(14) C19 0.0693(13) 0.0608(12) 0.0873(18) 0.0198(12) 0.0004(12) 0.0168(10) C20 0.0752(13) 0.0425(9) 0.0569(14) 0.0078(9) 0.0065(10) 0.0145(9) C21 0.0560(10) 0.0409(9) 0.0425(11) 0.0139(8) 0.0061(8) 0.0048(7) C22 0.0559(10) 0.0406(8) 0.0421(11) 0.0148(8) 0.0099(7) 0.0073(7) C23 0.0644(11) 0.0509(10) 0.0524(13) 0.0149(9) 0.0018(9) 0.0180(9) C24 0.0841(15) 0.0526(11) 0.0680(15) 0.0152(11) 0.0075(11) 0.0301(10) N1 0.0503(8) 0.0382(7) 0.0495(10) 0.0135(7) 0.0033(7) -0.0013(6) N2 0.0546(8) 0.0321(7) 0.0546(10) 0.0142(7) 0.0133(7) -0.0013(6) O1 0.0525(6) 0.0297(5) 0.0471(8) 0.0095(5) 0.0079(5) -0.0030(5) O2 0.0736(9) 0.0464(7) 0.0660(9) 0.0182(6) 0.0218(7) -0.0112(6) O3 0.0643(8) 0.0473(7) 0.0511(9) 0.0099(6) -0.0020(6) 0.0050(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.318(2) . ? C1 C2 1.400(3) . ? C1 H1 0.9300 . ? C2 C3 1.342(3) . ? C2 H2 0.9300 . ? C3 C4 1.411(3) . ? C3 H3 0.9300 . ? C4 C6 1.399(3) . ? C4 C5 1.425(2) . ? C5 N1 1.355(2) . ? C5 C9 1.428(2) . ? C6 C7 1.351(3) . ? C6 H6 0.9300 . ? C7 C8 1.417(2) . ? C7 H7 0.9300 . ? C8 C9 1.356(3) . ? C8 H8 0.9300 . ? C9 O1 1.3741(18) . ? C10 O1 1.4270(18) . ? C10 C11 1.512(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.2240(19) . ? C11 N2 1.327(2) . ? C12 C13 1.390(3) . ? C12 C17 1.391(3) . ? C12 N2 1.442(2) . ? C13 C14 1.391(3) . ? C13 C19 1.491(3) . ? C14 C15 1.368(3) . ? C14 H14 0.9300 . ? C15 C16 1.374(4) . ? C15 H15 0.9300 . ? C16 C17 1.396(3) . ? C16 H16 0.9300 . ? C17 C18 1.497(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.356(3) . ? C20 C24 1.410(3) 2_676 ? C20 H20 0.9300 . ? C21 O3 1.365(2) . ? C21 C22 1.426(2) . ? C22 C23 1.410(3) . ? C22 C22 1.415(4) 2_676 ? C23 C24 1.361(3) . ? C23 H23 0.9300 . ? C24 C20 1.410(3) 2_676 ? C24 H24 0.9300 . ? N2 H2N 0.85(2) . ? O3 H3O 0.98(3) . ? 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 C2 124.1(2) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C3 C2 C1 118.42(18) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 120.72(16) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C6 C4 C3 123.70(16) . . ? C6 C4 C5 119.48(16) . . ? C3 C4 C5 116.81(18) . . ? N1 C5 C4 121.83(15) . . ? N1 C5 C9 119.51(14) . . ? C4 C5 C9 118.66(17) . . ? C7 C6 C4 120.55(16) . . ? C7 C6 H6 119.7 . . ? C4 C6 H6 119.7 . . ? C6 C7 C8 120.9(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 120.48(18) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 O1 125.32(15) . . ? C8 C9 C5 119.96(15) . . ? O1 C9 C5 114.72(15) . . ? O1 C10 C11 111.71(14) . . ? O1 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? O1 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? O2 C11 N2 124.02(15) . . ? O2 C11 C10 117.29(16) . . ? N2 C11 C10 118.68(13) . . ? C13 C12 C17 122.12(16) . . ? C13 C12 N2 119.58(16) . . ? C17 C12 N2 118.29(17) . . ? C12 C13 C14 117.84(19) . . ? C12 C13 C19 122.05(16) . . ? C14 C13 C19 120.11(19) . . ? C15 C14 C13 121.1(2) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 120.7(2) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 117.8(2) . . ? C12 C17 C18 121.30(18) . . ? C16 C17 C18 120.9(2) . . ? 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 . . ? C13 C19 H19A 109.5 . . ? C13 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C13 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C24 119.79(18) . 2_676 ? C21 C20 H20 120.1 . . ? C24 C20 H20 120.1 2_676 . ? C20 C21 O3 123.10(17) . . ? C20 C21 C22 121.15(17) . . ? O3 C21 C22 115.71(16) . . ? C23 C22 C22 119.6(2) . 2_676 ? C23 C22 C21 122.19(17) . . ? C22 C22 C21 118.2(2) 2_676 . ? C24 C23 C22 120.16(19) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C20 121.1(2) . 2_676 ? C23 C24 H24 119.5 . . ? C20 C24 H24 119.5 2_676 . ? C1 N1 C5 118.17(15) . . ? C11 N2 C12 122.56(14) . . ? C11 N2 H2N 119.3(13) . . ? C12 N2 H2N 118.0(13) . . ? C9 O1 C10 115.99(13) . . ? C21 O3 H3O 109.6(16) . . ? 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 C3 0.2(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C6 -179.05(19) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C6 C4 C5 N1 179.23(16) . . . . ? C3 C4 C5 N1 -0.3(2) . . . . ? C6 C4 C5 C9 -0.2(2) . . . . ? C3 C4 C5 C9 -179.72(15) . . . . ? C3 C4 C6 C7 -179.48(19) . . . . ? C5 C4 C6 C7 1.0(3) . . . . ? C4 C6 C7 C8 -0.8(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C7 C8 C9 O1 -178.70(18) . . . . ? C7 C8 C9 C5 1.1(3) . . . . ? N1 C5 C9 C8 179.71(17) . . . . ? C4 C5 C9 C8 -0.8(2) . . . . ? N1 C5 C9 O1 -0.5(2) . . . . ? C4 C5 C9 O1 178.95(14) . . . . ? O1 C10 C11 O2 171.97(16) . . . . ? O1 C10 C11 N2 -9.3(2) . . . . ? C17 C12 C13 C14 -0.6(3) . . . . ? N2 C12 C13 C14 -179.43(18) . . . . ? C17 C12 C13 C19 178.50(19) . . . . ? N2 C12 C13 C19 -0.3(3) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C19 C13 C14 C15 -179.2(2) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C14 C15 C16 C17 0.4(4) . . . . ? C13 C12 C17 C16 1.1(3) . . . . ? N2 C12 C17 C16 179.93(18) . . . . ? C13 C12 C17 C18 -177.38(19) . . . . ? N2 C12 C17 C18 1.4(3) . . . . ? C15 C16 C17 C12 -1.0(3) . . . . ? C15 C16 C17 C18 177.5(2) . . . . ? C24 C20 C21 O3 177.17(17) 2_676 . . . ? C24 C20 C21 C22 -0.5(3) 2_676 . . . ? C20 C21 C22 C23 -179.20(18) . . . . ? O3 C21 C22 C23 3.0(2) . . . . ? C20 C21 C22 C22 0.8(3) . . . 2_676 ? O3 C21 C22 C22 -177.08(18) . . . 2_676 ? C22 C22 C23 C24 1.1(3) 2_676 . . . ? C21 C22 C23 C24 -178.94(18) . . . . ? C22 C23 C24 C20 -1.4(3) . . . 2_676 ? C2 C1 N1 C5 -0.1(3) . . . . ? C4 C5 N1 C1 0.1(3) . . . . ? C9 C5 N1 C1 179.54(17) . . . . ? O2 C11 N2 C12 2.1(3) . . . . ? C10 C11 N2 C12 -176.52(17) . . . . ? C13 C12 N2 C11 -77.6(2) . . . . ? C17 C12 N2 C11 103.6(2) . . . . ? C8 C9 O1 C10 -1.7(2) . . . . ? C5 C9 O1 C10 178.57(14) . . . . ? C11 C10 O1 C9 -179.09(14) . . . . ? _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.853 _refine_diff_density_max 0.140 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.031 # Attachment 'quinmpea_0m.cif' data_quinmpea_0m _database_code_depnum_ccdc_archive 'CCDC 625308' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N2 O3' _chemical_formula_weight 336.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.11390(10) _cell_length_b 13.4807(3) _cell_length_c 24.8362(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1712.18(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2214 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 18.98 _exptl_crystal_description needles _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.089 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18583 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0616 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.34 _reflns_number_total 4201 _reflns_number_gt 2329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0419P)^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 SHELXL _refine_ls_extinction_coef 0.0027(11) _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 -1.0(14) _refine_ls_number_reflns 4201 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1171 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 0.5401(5) 0.85863(18) 0.28605(9) 0.0621(6) Uani 1 1 d . . . H1 H 0.6279 0.7996 0.2931 0.075 Uiso 1 1 calc R . . C2 C 0.6096(5) 0.9425(2) 0.31608(10) 0.0709(7) Uani 1 1 d . . . H2 H 0.7402 0.9386 0.3420 0.085 Uiso 1 1 calc R . . C3 C 0.4855(6) 1.02869(19) 0.30693(10) 0.0664(7) Uani 1 1 d . . . H3 H 0.5303 1.0851 0.3264 0.080 Uiso 1 1 calc R . . C4 C 0.2875(5) 1.03323(16) 0.26772(9) 0.0518(6) Uani 1 1 d . . . C5 C 0.2323(5) 0.94469(15) 0.23896(8) 0.0453(5) Uani 1 1 d . . . C6 C 0.1451(6) 1.12012(18) 0.25671(10) 0.0686(8) Uani 1 1 d . . . H6 H 0.1816 1.1782 0.2755 0.082 Uiso 1 1 calc R . . C7 C -0.0466(6) 1.11946(17) 0.21852(10) 0.0691(7) Uani 1 1 d . . . H7 H -0.1419 1.1770 0.2121 0.083 Uiso 1 1 calc R . . C8 C -0.1027(5) 1.03313(16) 0.18870(10) 0.0600(7) Uani 1 1 d . . . H8 H -0.2321 1.0343 0.1624 0.072 Uiso 1 1 calc R . . C9 C 0.0326(4) 0.94813(15) 0.19848(8) 0.0469(5) Uani 1 1 d . . . C10 C -0.2302(4) 0.85498(15) 0.13757(8) 0.0530(6) Uani 1 1 d . . . H10A H -0.2191 0.9060 0.1101 0.064 Uiso 1 1 calc R . . H10B H -0.3863 0.8670 0.1588 0.064 Uiso 1 1 calc R . . C11 C -0.2487(5) 0.75478(15) 0.11118(8) 0.0455(5) Uani 1 1 d . . . C12 C -0.0171(5) 0.61043(15) 0.07619(8) 0.0538(6) Uani 1 1 d . . . H12A H -0.1853 0.5779 0.0797 0.065 Uiso 1 1 calc R . . H12B H 0.1127 0.5689 0.0936 0.065 Uiso 1 1 calc R . . C13 C 0.0496(5) 0.62013(15) 0.01749(8) 0.0646(7) Uani 1 1 d . . . H13A H 0.2168 0.6535 0.0141 0.077 Uiso 1 1 calc R . . H13B H -0.0813 0.6612 0.0001 0.077 Uiso 1 1 calc R . . C14 C 0.0636(5) 0.52135(16) -0.01133(8) 0.0515(6) Uani 1 1 d . . . C15 C 0.2549(5) 0.45247(18) 0.00089(9) 0.0610(6) Uani 1 1 d . . . H15 H 0.3740 0.4667 0.0281 0.073 Uiso 1 1 calc R . . C16 C 0.2747(5) 0.36265(17) -0.02615(9) 0.0601(6) Uani 1 1 d . . . H16 H 0.4058 0.3179 -0.0171 0.072 Uiso 1 1 calc R . . C17 C 0.1006(5) 0.34019(17) -0.06624(9) 0.0522(6) Uani 1 1 d . . . C18 C -0.0931(5) 0.40734(18) -0.07871(9) 0.0597(7) Uani 1 1 d . . . H18 H -0.2128 0.3926 -0.1057 0.072 Uiso 1 1 calc R . . C19 C -0.1115(5) 0.49630(17) -0.05153(9) 0.0582(6) Uani 1 1 d . . . H19 H -0.2445 0.5404 -0.0604 0.070 Uiso 1 1 calc R . . C20 C 0.3132(6) 0.18791(19) -0.08803(11) 0.0896(9) Uani 1 1 d . . . H20A H 0.4750 0.2207 -0.0963 0.134 Uiso 1 1 calc R . . H20B H 0.2921 0.1315 -0.1112 0.134 Uiso 1 1 calc R . . H20C H 0.3151 0.1664 -0.0512 0.134 Uiso 1 1 calc R . . H2N H 0.117(6) 0.7329(17) 0.1128(10) 0.082(9) Uiso 1 1 d . . . N1 N 0.3587(4) 0.85782(13) 0.24842(7) 0.0524(5) Uani 1 1 d . . . N2 N -0.0273(4) 0.70594(14) 0.10364(7) 0.0508(5) Uani 1 1 d . . . O1 O -0.0063(3) 0.86000(10) 0.17140(5) 0.0549(4) Uani 1 1 d . . . O2 O -0.4625(3) 0.72432(12) 0.09652(7) 0.0659(5) Uani 1 1 d . . . O3 O 0.1021(4) 0.25477(13) -0.09607(7) 0.0754(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 0.0639(16) 0.0673(17) 0.0551(14) -0.0024(13) -0.0066(14) 0.0062(14) C2 0.0735(18) 0.0822(18) 0.0569(16) -0.0142(15) -0.0100(14) -0.0029(17) C3 0.0792(18) 0.0647(17) 0.0555(15) -0.0165(13) 0.0027(15) -0.0198(16) C4 0.0631(17) 0.0444(15) 0.0478(13) -0.0049(11) 0.0115(12) -0.0077(13) C5 0.0518(14) 0.0430(13) 0.0412(12) -0.0029(10) 0.0091(12) -0.0056(12) C6 0.097(2) 0.0455(15) 0.0632(16) -0.0069(13) 0.0102(16) -0.0052(15) C7 0.092(2) 0.0394(15) 0.0756(18) 0.0028(13) 0.0163(17) 0.0098(14) C8 0.0668(16) 0.0526(15) 0.0607(15) 0.0051(13) 0.0029(13) 0.0052(14) C9 0.0551(14) 0.0375(12) 0.0482(13) -0.0042(10) 0.0070(12) -0.0014(11) C10 0.0484(13) 0.0604(15) 0.0501(13) -0.0029(11) -0.0045(11) 0.0065(13) C11 0.0389(12) 0.0590(14) 0.0387(11) 0.0033(10) -0.0003(11) -0.0020(13) C12 0.0544(14) 0.0526(14) 0.0544(14) -0.0037(11) -0.0020(12) -0.0032(13) C13 0.0790(18) 0.0573(14) 0.0574(15) 0.0009(12) 0.0045(13) -0.0058(14) C14 0.0567(14) 0.0542(15) 0.0436(13) 0.0013(11) 0.0091(11) -0.0040(13) C15 0.0556(14) 0.0726(16) 0.0549(14) -0.0113(13) -0.0067(14) -0.0026(15) C16 0.0518(14) 0.0674(16) 0.0610(14) -0.0110(13) -0.0031(13) 0.0099(14) C17 0.0501(14) 0.0590(15) 0.0476(13) -0.0086(12) 0.0039(12) -0.0011(12) C18 0.0547(16) 0.0689(16) 0.0555(15) -0.0069(13) -0.0078(13) -0.0024(13) C19 0.0533(15) 0.0620(16) 0.0594(15) 0.0043(13) 0.0000(13) 0.0071(12) C20 0.089(2) 0.0782(18) 0.102(2) -0.0337(17) -0.0034(18) 0.0120(18) N1 0.0572(12) 0.0500(12) 0.0501(11) -0.0040(9) -0.0015(10) 0.0023(10) N2 0.0421(12) 0.0538(12) 0.0563(12) -0.0118(9) -0.0066(10) -0.0046(11) O1 0.0550(9) 0.0512(9) 0.0584(9) -0.0109(7) -0.0142(8) 0.0040(8) O2 0.0380(9) 0.0831(11) 0.0766(11) -0.0062(9) -0.0063(8) -0.0070(9) O3 0.0748(12) 0.0742(11) 0.0773(12) -0.0250(10) -0.0113(10) 0.0094(10) _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 1.317(3) . ? C1 C2 1.401(3) . ? C1 H1 0.9300 . ? C2 C3 1.343(3) . ? C2 H2 0.9300 . ? C3 C4 1.406(3) . ? C3 H3 0.9300 . ? C4 C6 1.406(3) . ? C4 C5 1.419(3) . ? C5 N1 1.358(3) . ? C5 C9 1.434(3) . ? C6 C7 1.364(3) . ? C6 H6 0.9300 . ? C7 C8 1.409(3) . ? C7 H7 0.9300 . ? C8 C9 1.360(3) . ? C8 H8 0.9300 . ? C9 O1 1.380(2) . ? C10 O1 1.421(2) . ? C10 C11 1.504(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.224(2) . ? C11 N2 1.323(3) . ? C12 N2 1.458(3) . ? C12 C13 1.503(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.513(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.383(3) . ? C14 C15 1.382(3) . ? C15 C16 1.388(3) . ? C15 H15 0.9300 . ? C16 C17 1.370(3) . ? C16 H16 0.9300 . ? C17 O3 1.369(3) . ? C17 C18 1.377(3) . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O3 1.420(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N2 H2N 0.85(3) . ? 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 C2 124.3(2) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C6 C4 C3 122.9(2) . . ? C6 C4 C5 120.0(2) . . ? C3 C4 C5 117.1(2) . . ? N1 C5 C4 122.9(2) . . ? N1 C5 C9 119.22(18) . . ? C4 C5 C9 117.9(2) . . ? C7 C6 C4 120.1(2) . . ? C7 C6 H6 119.9 . . ? C4 C6 H6 119.9 . . ? C6 C7 C8 121.2(2) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 O1 124.4(2) . . ? C8 C9 C5 120.98(19) . . ? O1 C9 C5 114.62(18) . . ? O1 C10 C11 110.54(17) . . ? O1 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O2 C11 N2 123.8(2) . . ? O2 C11 C10 119.2(2) . . ? N2 C11 C10 117.0(2) . . ? N2 C12 C13 112.64(17) . . ? N2 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N2 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 C14 113.14(18) . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C19 C14 C15 116.9(2) . . ? C19 C14 C13 121.7(2) . . ? C15 C14 C13 121.4(2) . . ? C14 C15 C16 122.1(2) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 O3 125.1(2) . . ? C16 C17 C18 119.1(2) . . ? O3 C17 C18 115.8(2) . . ? C17 C18 C19 120.7(2) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 121.4(2) . . ? C18 C19 H19 119.3 . . ? C14 C19 H19 119.3 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 N1 C5 116.80(19) . . ? C11 N2 C12 122.4(2) . . ? C11 N2 H2N 119.3(16) . . ? C12 N2 H2N 118.1(17) . . ? C9 O1 C10 116.44(17) . . ? C17 O3 C20 117.52(19) . . ? 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 C3 0.3(4) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C2 C3 C4 C6 178.6(2) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C6 C4 C5 N1 -178.6(2) . . . . ? C3 C4 C5 N1 0.9(3) . . . . ? C6 C4 C5 C9 1.0(3) . . . . ? C3 C4 C5 C9 -179.4(2) . . . . ? C3 C4 C6 C7 -179.3(2) . . . . ? C5 C4 C6 C7 0.2(3) . . . . ? C4 C6 C7 C8 -1.2(4) . . . . ? C6 C7 C8 C9 1.1(4) . . . . ? C7 C8 C9 O1 -179.6(2) . . . . ? C7 C8 C9 C5 0.2(3) . . . . ? N1 C5 C9 C8 178.4(2) . . . . ? C4 C5 C9 C8 -1.2(3) . . . . ? N1 C5 C9 O1 -1.7(3) . . . . ? C4 C5 C9 O1 178.63(19) . . . . ? O1 C10 C11 O2 154.92(19) . . . . ? O1 C10 C11 N2 -27.3(3) . . . . ? N2 C12 C13 C14 179.4(2) . . . . ? C12 C13 C14 C19 114.6(2) . . . . ? C12 C13 C14 C15 -66.3(3) . . . . ? C19 C14 C15 C16 0.9(3) . . . . ? C13 C14 C15 C16 -178.2(2) . . . . ? C14 C15 C16 C17 -0.2(4) . . . . ? C15 C16 C17 O3 179.2(2) . . . . ? C15 C16 C17 C18 -0.5(3) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? O3 C17 C18 C19 -179.4(2) . . . . ? C17 C18 C19 C14 0.4(4) . . . . ? C15 C14 C19 C18 -1.0(3) . . . . ? C13 C14 C19 C18 178.1(2) . . . . ? C2 C1 N1 C5 -0.3(3) . . . . ? C4 C5 N1 C1 -0.3(3) . . . . ? C9 C5 N1 C1 -179.93(19) . . . . ? O2 C11 N2 C12 0.7(3) . . . . ? C10 C11 N2 C12 -176.95(18) . . . . ? C13 C12 N2 C11 96.0(3) . . . . ? C8 C9 O1 C10 -10.5(3) . . . . ? C5 C9 O1 C10 169.70(17) . . . . ? C11 C10 O1 C9 -179.49(17) . . . . ? C16 C17 O3 C20 -5.6(3) . . . . ? C18 C17 O3 C20 174.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.116 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.029 data_dmah2o _database_code_depnum_ccdc_archive 'CCDC 632254' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 N2 O3' _chemical_formula_weight 324.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.4877(15) _cell_length_b 12.6863(19) _cell_length_c 14.832(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1785.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 13050 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3962 _reflns_number_gt 2123 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0896P)^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(17) _refine_ls_number_reflns 3962 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1017 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _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 0.9778(3) 0.8507(2) 0.62564(18) 0.0760(8) Uani 1 1 d . . . C2 C 0.9088(4) 0.9423(3) 0.5955(3) 0.1163(13) Uani 1 1 d . . . C6 C 1.0590(4) 0.7863(4) 0.5721(2) 0.1186(15) Uani 1 1 d . . . C4 C 1.0050(12) 0.9059(9) 0.4523(5) 0.251(8) Uani 1 1 d . . . H4 H 1.0196 0.9273 0.3930 0.301 Uiso 1 1 calc R . . C7 C 1.1335(5) 0.6927(4) 0.6065(4) 0.178(3) Uani 1 1 d . . . H6A H 1.1897 0.7121 0.6577 0.267 Uiso 1 1 calc R . . H6B H 1.1933 0.6648 0.5601 0.267 Uiso 1 1 calc R . . H6C H 1.0659 0.6403 0.6241 0.267 Uiso 1 1 calc R . . C8 C 0.8218(5) 1.0065(3) 0.6589(4) 0.174(2) Uani 1 1 d . . . H8A H 0.7385 0.9680 0.6750 0.261 Uiso 1 1 calc R . . H8B H 0.7956 1.0715 0.6302 0.261 Uiso 1 1 calc R . . H8C H 0.8756 1.0215 0.7122 0.261 Uiso 1 1 calc R . . C3 C 0.9218(8) 0.9682(6) 0.5056(4) 0.199(4) Uani 1 1 d . . . H3 H 0.8753 1.0265 0.4818 0.239 Uiso 1 1 calc R . . C5 C 1.0683(8) 0.8147(7) 0.4796(4) 0.206(5) Uani 1 1 d . . . H5 H 1.1163 0.7722 0.4387 0.248 Uiso 1 1 calc R . . C16 C 1.0117(2) 0.88106(17) 1.03805(15) 0.0576(6) Uani 1 1 d . . . C15 C 1.0151(3) 0.87735(19) 1.13262(16) 0.0666(7) Uani 1 1 d . . . C11 C 0.9456(3) 0.79702(18) 0.99035(16) 0.0635(6) Uani 1 1 d . . . C12 C 0.8839(3) 0.7163(2) 1.03655(18) 0.0821(8) Uani 1 1 d . . . H11 H 0.8377 0.6628 1.0055 0.099 Uiso 1 1 calc R . . C19 C 1.1254(3) 1.0395(2) 1.03600(19) 0.0784(7) Uani 1 1 d . . . H18 H 1.1622 1.0960 1.0036 0.094 Uiso 1 1 calc R . . C18 C 1.1355(3) 1.0430(2) 1.1292(2) 0.0872(8) Uani 1 1 d . . . H17 H 1.1782 1.0997 1.1581 0.105 Uiso 1 1 calc R . . C17 C 1.0814(3) 0.9616(2) 1.17700(19) 0.0804(8) Uani 1 1 d . . . H16 H 1.0883 0.9614 1.2395 0.096 Uiso 1 1 calc R . . C13 C 0.8905(4) 0.7142(2) 1.1308(2) 0.0923(9) Uani 1 1 d . . . H12 H 0.8496 0.6581 1.1616 0.111 Uiso 1 1 calc R . . C14 C 0.9535(3) 0.7903(2) 1.17789(18) 0.0834(8) Uani 1 1 d . . . H13 H 0.9570 0.7864 1.2405 0.100 Uiso 1 1 calc R . . C10 C 0.8728(4) 0.7296(2) 0.84846(17) 0.0829(8) Uani 1 1 d . . . H9A H 0.7746 0.7312 0.8665 0.099 Uiso 1 1 calc R . . H9B H 0.9098 0.6602 0.8622 0.099 Uiso 1 1 calc R . . N1 N 1.0675(2) 0.96201(15) 0.99005(12) 0.0657(6) Uani 1 1 d . . . N2 N 0.9650(2) 0.82583(17) 0.71917(13) 0.0680(6) Uani 1 1 d . . . C9 C 0.8826(3) 0.74819(18) 0.74927(17) 0.0675(6) Uani 1 1 d . . . O2 O 0.9486(2) 0.80613(13) 0.89843(11) 0.0765(5) Uani 1 1 d . . . O1 O 0.8130(2) 0.69055(14) 0.69930(12) 0.0866(6) Uani 1 1 d . . . O3 O 0.1433(2) 0.97019(16) 0.80877(14) 0.0781(5) Uani 1 1 d . . . H3A H 0.105(5) 0.974(3) 0.866(3) 0.134(14) Uiso 1 1 d . . . H3B H 0.162(3) 1.032(2) 0.799(2) 0.099(11) Uiso 1 1 d . . . H2N H 1.006(3) 0.869(2) 0.761(2) 0.087(9) 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 C1 0.0660(17) 0.095(2) 0.0665(17) -0.0049(14) -0.0008(13) -0.0212(15) C2 0.099(3) 0.129(3) 0.121(3) 0.046(2) -0.038(2) -0.040(2) C6 0.090(2) 0.170(4) 0.096(3) -0.070(2) 0.0353(19) -0.064(2) C4 0.283(12) 0.369(16) 0.101(4) 0.034(7) -0.026(5) -0.251(12) C7 0.097(3) 0.160(4) 0.277(6) -0.130(4) 0.039(4) 0.001(3) C8 0.119(3) 0.125(3) 0.278(7) 0.045(4) -0.018(4) 0.035(3) C3 0.201(7) 0.247(8) 0.148(5) 0.111(5) -0.096(5) -0.129(6) C5 0.196(7) 0.303(10) 0.120(5) -0.103(5) 0.078(5) -0.181(8) C16 0.0548(13) 0.0596(14) 0.0585(15) -0.0006(10) 0.0013(11) -0.0027(11) C15 0.0611(15) 0.0786(18) 0.0599(16) 0.0005(11) -0.0019(11) -0.0027(13) C11 0.0690(15) 0.0634(15) 0.0581(15) 0.0053(10) -0.0016(11) -0.0062(12) C12 0.0973(19) 0.0725(17) 0.0766(18) 0.0055(13) -0.0050(15) -0.0264(14) C19 0.0867(18) 0.0742(17) 0.0744(18) -0.0032(12) -0.0003(15) -0.0245(14) C18 0.093(2) 0.086(2) 0.082(2) -0.0161(15) -0.0092(16) -0.0206(16) C17 0.0807(18) 0.100(2) 0.0606(16) -0.0088(14) -0.0042(13) -0.0107(15) C13 0.110(2) 0.081(2) 0.085(2) 0.0236(15) 0.0038(17) -0.0252(17) C14 0.097(2) 0.091(2) 0.0628(16) 0.0119(14) 0.0009(15) -0.0138(16) C10 0.107(2) 0.0702(17) 0.0711(17) -0.0072(12) -0.0088(15) -0.0243(16) N1 0.0703(13) 0.0643(13) 0.0626(12) -0.0010(9) 0.0020(10) -0.0134(10) N2 0.0753(13) 0.0678(13) 0.0609(13) -0.0104(10) 0.0009(10) -0.0053(11) C9 0.0762(16) 0.0554(14) 0.0709(16) -0.0119(12) -0.0009(14) -0.0041(12) O2 0.0971(13) 0.0731(12) 0.0594(11) -0.0050(8) -0.0022(9) -0.0269(10) O1 0.1051(14) 0.0754(11) 0.0791(11) -0.0173(10) -0.0094(11) -0.0208(10) O3 0.0985(14) 0.0691(13) 0.0667(12) 0.0019(8) 0.0091(11) -0.0180(10) _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 C6 1.376(4) . ? C1 C2 1.406(5) . ? C1 N2 1.428(3) . ? C2 C3 1.379(6) . ? C2 C8 1.493(6) . ? C6 C5 1.421(7) . ? C6 C7 1.473(7) . ? C4 C5 1.365(14) . ? C4 C3 1.369(13) . ? C4 H4 0.9300 . ? C7 H6A 0.9600 . ? C7 H6B 0.9600 . ? C7 H6C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C3 H3 0.9300 . ? C5 H5 0.9300 . ? C16 N1 1.357(3) . ? C16 C15 1.404(3) . ? C16 C11 1.425(3) . ? C15 C17 1.404(3) . ? C15 C14 1.418(4) . ? C11 C12 1.364(3) . ? C11 O2 1.368(3) . ? C12 C13 1.400(4) . ? C12 H11 0.9300 . ? C19 N1 1.317(3) . ? C19 C18 1.386(4) . ? C19 H18 0.9300 . ? C18 C17 1.354(4) . ? C18 H17 0.9300 . ? C17 H16 0.9300 . ? C13 C14 1.333(4) . ? C13 H12 0.9300 . ? C14 H13 0.9300 . ? C10 O2 1.417(3) . ? C10 C9 1.493(3) . ? C10 H9A 0.9700 . ? C10 H9B 0.9700 . ? N2 C9 1.335(3) . ? N2 H2N 0.92(3) . ? C9 O1 1.233(3) . ? O3 H3A 0.92(4) . ? O3 H3B 0.82(3) . ? 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 C6 C1 C2 124.6(4) . . ? C6 C1 N2 118.5(3) . . ? C2 C1 N2 116.9(3) . . ? C3 C2 C1 117.6(5) . . ? C3 C2 C8 121.9(5) . . ? C1 C2 C8 120.5(4) . . ? C1 C6 C5 116.2(5) . . ? C1 C6 C7 123.2(4) . . ? C5 C6 C7 120.6(5) . . ? C5 C4 C3 124.9(8) . . ? C5 C4 H4 117.6 . . ? C3 C4 H4 117.6 . . ? C6 C7 H6A 109.5 . . ? C6 C7 H6B 109.5 . . ? H6A C7 H6B 109.5 . . ? C6 C7 H6C 109.5 . . ? H6A C7 H6C 109.5 . . ? H6B C7 H6C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C3 C2 118.2(8) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C4 C5 C6 118.3(7) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? N1 C16 C15 122.7(2) . . ? N1 C16 C11 118.51(19) . . ? C15 C16 C11 118.7(2) . . ? C16 C15 C17 116.9(2) . . ? C16 C15 C14 119.3(2) . . ? C17 C15 C14 123.7(2) . . ? C12 C11 O2 124.9(2) . . ? C12 C11 C16 120.1(2) . . ? O2 C11 C16 114.98(19) . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H11 120.1 . . ? C13 C12 H11 120.1 . . ? N1 C19 C18 124.7(3) . . ? N1 C19 H18 117.7 . . ? C18 C19 H18 117.7 . . ? C17 C18 C19 118.1(3) . . ? C17 C18 H17 120.9 . . ? C19 C18 H17 120.9 . . ? C18 C17 C15 120.3(2) . . ? C18 C17 H16 119.8 . . ? C15 C17 H16 119.8 . . ? C14 C13 C12 122.0(3) . . ? C14 C13 H12 119.0 . . ? C12 C13 H12 119.0 . . ? C13 C14 C15 120.0(2) . . ? C13 C14 H13 120.0 . . ? C15 C14 H13 120.0 . . ? O2 C10 C9 112.1(2) . . ? O2 C10 H9A 109.2 . . ? C9 C10 H9A 109.2 . . ? O2 C10 H9B 109.2 . . ? C9 C10 H9B 109.2 . . ? H9A C10 H9B 107.9 . . ? C19 N1 C16 117.2(2) . . ? C9 N2 C1 122.5(2) . . ? C9 N2 H2N 117.9(18) . . ? C1 N2 H2N 119.1(18) . . ? O1 C9 N2 123.4(2) . . ? O1 C9 C10 117.8(2) . . ? N2 C9 C10 118.8(2) . . ? C11 O2 C10 116.91(18) . . ? H3A O3 H3B 101(3) . . ? 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 1.1(5) . . . . ? N2 C1 C2 C3 179.1(3) . . . . ? C6 C1 C2 C8 179.5(3) . . . . ? N2 C1 C2 C8 -2.5(5) . . . . ? C2 C1 C6 C5 -2.0(5) . . . . ? N2 C1 C6 C5 -179.9(3) . . . . ? C2 C1 C6 C7 178.1(3) . . . . ? N2 C1 C6 C7 0.1(4) . . . . ? C5 C4 C3 C2 5.3(13) . . . . ? C1 C2 C3 C4 -2.4(8) . . . . ? C8 C2 C3 C4 179.2(6) . . . . ? C3 C4 C5 C6 -6.2(13) . . . . ? C1 C6 C5 C4 4.2(8) . . . . ? C7 C6 C5 C4 -175.8(6) . . . . ? N1 C16 C15 C17 -0.9(3) . . . . ? C11 C16 C15 C17 179.9(2) . . . . ? N1 C16 C15 C14 179.5(2) . . . . ? C11 C16 C15 C14 0.3(3) . . . . ? N1 C16 C11 C12 -177.6(2) . . . . ? C15 C16 C11 C12 1.7(4) . . . . ? N1 C16 C11 O2 1.5(3) . . . . ? C15 C16 C11 O2 -179.2(2) . . . . ? O2 C11 C12 C13 178.5(3) . . . . ? C16 C11 C12 C13 -2.4(4) . . . . ? N1 C19 C18 C17 -0.4(5) . . . . ? C19 C18 C17 C15 -1.1(4) . . . . ? C16 C15 C17 C18 1.7(4) . . . . ? C14 C15 C17 C18 -178.7(3) . . . . ? C11 C12 C13 C14 1.2(5) . . . . ? C12 C13 C14 C15 0.7(5) . . . . ? C16 C15 C14 C13 -1.5(4) . . . . ? C17 C15 C14 C13 179.0(3) . . . . ? C18 C19 N1 C16 1.3(4) . . . . ? C15 C16 N1 C19 -0.6(3) . . . . ? C11 C16 N1 C19 178.7(2) . . . . ? C6 C1 N2 C9 -76.5(3) . . . . ? C2 C1 N2 C9 105.4(3) . . . . ? C1 N2 C9 O1 1.4(4) . . . . ? C1 N2 C9 C10 -178.4(3) . . . . ? O2 C10 C9 O1 -175.3(2) . . . . ? O2 C10 C9 N2 4.5(4) . . . . ? C12 C11 O2 C10 4.8(4) . . . . ? C16 C11 O2 C10 -174.3(2) . . . . ? C9 C10 O2 C11 179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.162 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.033