# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ardppme_0m _database_code_depnum_ccdc_archive 'CCDC 886519' #TrackingRef '11917_web_deposit_cif_file_0_AsishRDas_1339673120.CIFFINAL.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H44 N4 O8' _chemical_formula_weight 876.93 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)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.188(5) _cell_length_b 14.671(5) _cell_length_c 17.440(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 93.406(5) _cell_angle_gamma 90.000(5) _cell_volume 4390(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9770 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_reflns_number 26201 _diffrn_reflns_av_R_equivalents 0.0730 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 24.03 _reflns_number_total 6847 _reflns_number_gt 4524 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1550P)^2^+32.0908P] 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 6847 _refine_ls_number_parameters 620 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1670 _refine_ls_R_factor_gt 0.1290 _refine_ls_wR_factor_ref 0.3982 _refine_ls_wR_factor_gt 0.3723 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.196 _refine_ls_shift/su_mean 0.006 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 O7 O 1.0317(4) 0.6414(5) 0.6988(4) 0.0542(19) Uani 1 1 d . . . O5 O 0.8663(3) 0.4726(4) 0.7819(4) 0.0563(16) Uani 1 1 d . . . O4 O 0.1976(4) 0.8368(4) 1.0004(3) 0.0554(15) Uani 1 1 d . . . O8 O 1.0011(3) 0.8120(4) 0.6939(4) 0.0571(16) Uani 1 1 d . . . O3 O 0.1991(4) 0.6693(4) 1.0345(3) 0.0588(16) Uani 1 1 d . . . H70 H 0.1863 0.7190 1.0162 0.088 Uiso 1 1 calc R . . O6 O 0.7701(4) 0.5448(4) 0.7206(4) 0.0625(17) Uani 1 1 d . . . O1 O 0.3128(4) 0.5151(4) 0.8807(4) 0.0628(17) Uani 1 1 d . . . O2 O 0.2523(4) 0.5830(4) 0.7822(4) 0.0603(16) Uani 1 1 d . . . N4 N 0.9076(4) 0.9000(4) 0.7512(4) 0.0494(17) Uani 1 1 d . . . N3 N 0.8300(4) 0.8854(5) 0.7681(4) 0.0481(17) Uani 1 1 d . . . N2 N 0.2339(5) 0.9332(5) 0.9025(4) 0.0540(18) Uani 1 1 d . . . N1 N 0.2402(5) 0.9248(5) 0.8242(4) 0.0536(19) Uani 1 1 d . . . C4 C 0.2798(5) 0.5442(5) 1.0090(5) 0.047(2) Uani 1 1 d . . . C31 C 1.0013(5) 0.5083(5) 0.7637(5) 0.0433(19) Uani 1 1 d . . . C2 C 0.2161(5) 0.6306(5) 0.9043(5) 0.0429(19) Uani 1 1 d . . . C37 C 0.8648(5) 0.6792(5) 0.6527(5) 0.0450(19) Uani 1 1 d . . . C29 C 0.8978(4) 0.6009(5) 0.7022(4) 0.0403(18) Uani 1 1 d . . . C30 C 0.9750(5) 0.5887(5) 0.7191(5) 0.0434(19) Uani 1 1 d . . . C10 C 0.1573(5) 0.6996(5) 0.8684(5) 0.0442(19) Uani 1 1 d . . . C1 C 0.2586(5) 0.5790(6) 0.8521(5) 0.047(2) Uani 1 1 d . . . C38 C 0.8983(5) 0.6884(6) 0.5755(5) 0.048(2) Uani 1 1 d . . . C11 C 0.0756(5) 0.6972(5) 0.8995(5) 0.0443(19) Uani 1 1 d . . . C19 C 0.2055(5) 0.8515(5) 0.9301(5) 0.050(2) Uani 1 1 d . . . C43 C 0.9218(5) 0.6136(6) 0.5336(5) 0.057(2) Uani 1 1 d . . . H41 H 0.9210 0.5560 0.5557 0.069 Uiso 1 1 calc R . . C22 C 0.2659(5) 1.0092(5) 0.9436(5) 0.050(2) Uani 1 1 d . . . C47A C 0.8045(4) 0.8065(5) 0.7317(5) 0.0439(19) Uani 1 1 d . . . C32 C 0.9440(5) 0.4555(6) 0.7960(5) 0.052(2) Uani 1 1 d . . . C18 C 0.1903(5) 0.7947(5) 0.8646(5) 0.047(2) Uani 1 1 d . . . C36 C 1.0799(5) 0.4874(6) 0.7805(5) 0.056(2) Uani 1 1 d . . . H30 H 1.1188 0.5227 0.7605 0.067 Uiso 1 1 calc R . . C45 C 0.8648(5) 0.7671(5) 0.6969(5) 0.047(2) Uani 1 1 d . . . C16 C 0.0449(5) 0.6171(6) 0.9288(5) 0.053(2) Uani 1 1 d . . . H12 H 0.0768 0.5662 0.9361 0.063 Uiso 1 1 calc R . . C3 C 0.2298(5) 0.6182(5) 0.9806(5) 0.046(2) Uani 1 1 d . . . C39 C 0.9013(6) 0.7719(6) 0.5370(5) 0.060(2) Uani 1 1 d . . . H46 H 0.8868 0.8245 0.5622 0.071 Uiso 1 1 calc R . . C46A C 0.9330(5) 0.8251(5) 0.7114(5) 0.047(2) Uani 1 1 d . . . C49A C 0.9516(5) 0.9687(5) 0.7899(5) 0.049(2) Uani 1 1 d . . . C15 C -0.0330(5) 0.6123(6) 0.9471(5) 0.058(2) Uani 1 1 d . . . H13 H -0.0526 0.5573 0.9642 0.070 Uiso 1 1 calc R . . C28 C 0.8405(5) 0.5416(5) 0.7318(5) 0.048(2) Uani 1 1 d . . . C5 C 0.3208(5) 0.4971(6) 0.9583(6) 0.056(2) Uani 1 1 d . . . C20 C 0.2101(5) 0.8408(6) 0.8020(5) 0.052(2) Uani 1 1 d . . . C42 C 0.9465(6) 0.6226(7) 0.4598(6) 0.068(3) Uani 1 1 d . . . H42 H 0.9625 0.5709 0.4343 0.081 Uiso 1 1 calc R . . C50A C 1.0213(6) 0.9946(6) 0.7601(7) 0.070(3) Uani 1 1 d . . . H52 H 1.0379 0.9692 0.7150 0.084 Uiso 1 1 calc R . . C9 C 0.2896(6) 0.5217(6) 1.0871(6) 0.060(2) Uani 1 1 d . . . H2 H 0.2624 0.5532 1.1232 0.073 Uiso 1 1 calc R . . C12 C 0.0267(5) 0.7710(6) 0.8957(6) 0.060(2) Uani 1 1 d . . . H17 H 0.0453 0.8263 0.8782 0.072 Uiso 1 1 calc R . . C40 C 0.9249(6) 0.7792(7) 0.4635(6) 0.066(3) Uani 1 1 d . . . H45 H 0.9251 0.8362 0.4401 0.079 Uiso 1 1 calc R . . C6 C 0.3756(6) 0.4307(7) 0.9790(6) 0.069(3) Uani 1 1 d . . . H5 H 0.4054 0.4024 0.9431 0.083 Uiso 1 1 calc R . . C14 C -0.0807(5) 0.6856(7) 0.9407(6) 0.061(2) Uani 1 1 d . . . C23 C 0.3159(6) 1.0688(7) 0.9087(6) 0.070(3) Uani 1 1 d . . . H23 H 0.3269 1.0609 0.8575 0.084 Uiso 1 1 calc R . . C41 C 0.9482(6) 0.7042(7) 0.4235(5) 0.062(2) Uani 1 1 d . . . C48A C 0.7226(5) 0.7762(6) 0.7350(6) 0.063(3) Uani 1 1 d . . . H47A H 0.7052 0.7498 0.6867 0.094 Uiso 1 1 calc R . . H47B H 0.6903 0.8276 0.7457 0.094 Uiso 1 1 calc R . . H47C H 0.7192 0.7316 0.7750 0.094 Uiso 1 1 calc R . . C33 C 0.9640(6) 0.3822(6) 0.8437(5) 0.060(2) Uani 1 1 d . . . H33 H 0.9258 0.3467 0.8649 0.072 Uiso 1 1 calc R . . C21 C 0.2021(6) 0.8151(7) 0.7198(5) 0.065(3) Uani 1 1 d . . . H21A H 0.2314 0.7605 0.7118 0.098 Uiso 1 1 calc R . . H21B H 0.2215 0.8635 0.6893 0.098 Uiso 1 1 calc R . . H21C H 0.1481 0.8045 0.7051 0.098 Uiso 1 1 calc R . . C13 C -0.0506(6) 0.7660(7) 0.9172(7) 0.073(3) Uani 1 1 d . . . H16 H -0.0815 0.8181 0.9154 0.088 Uiso 1 1 calc R . . C27 C 0.2478(7) 1.0225(7) 1.0175(6) 0.075(3) Uani 1 1 d . . . H24 H 0.2136 0.9838 1.0408 0.091 Uiso 1 1 calc R . . C24 C 0.3488(6) 1.1394(7) 0.9507(7) 0.076(3) Uani 1 1 d . . . H25 H 0.3829 1.1789 0.9278 0.091 Uiso 1 1 calc R . . C54A C 0.9252(7) 1.0092(7) 0.8532(7) 0.079(3) Uani 1 1 d . . . H56 H 0.8773 0.9922 0.8708 0.095 Uiso 1 1 calc R . . C35 C 1.0990(6) 0.4140(6) 0.8271(6) 0.066(3) Uani 1 1 d . . . H31 H 1.1511 0.3986 0.8370 0.080 Uiso 1 1 calc R . . C8 C 0.3400(7) 0.4524(7) 1.1097(6) 0.074(3) Uani 1 1 d . . . H3 H 0.3444 0.4352 1.1611 0.089 Uiso 1 1 calc R . . C25 C 0.3330(7) 1.1524(7) 1.0234(7) 0.079(3) Uani 1 1 d . . . H26 H 0.3568 1.2001 1.0510 0.095 Uiso 1 1 calc R . . C26 C 0.2826(8) 1.0970(8) 1.0580(7) 0.093(4) Uani 1 1 d . . . H27 H 0.2709 1.1081 1.1085 0.111 Uiso 1 1 calc R . . C7 C 0.3835(7) 0.4086(7) 1.0583(7) 0.076(3) Uani 1 1 d . . . H4 H 0.4187 0.3638 1.0753 0.091 Uiso 1 1 calc R . . C34 C 1.0424(6) 0.3635(6) 0.8588(6) 0.065(3) Uani 1 1 d . . . H32 H 1.0568 0.3154 0.8914 0.079 Uiso 1 1 calc R . . C51A C 1.0663(7) 1.0619(7) 0.8016(8) 0.090(4) Uani 1 1 d . . . H53 H 1.1143 1.0794 0.7843 0.108 Uiso 1 1 calc R . . C17 C -0.1661(6) 0.6848(8) 0.9624(7) 0.086(3) Uani 1 1 d . . . H15A H -0.1786 0.6260 0.9825 0.129 Uiso 1 1 calc R . . H15B H -0.1996 0.6974 0.9177 0.129 Uiso 1 1 calc R . . H15C H -0.1734 0.7305 1.0007 0.129 Uiso 1 1 calc R . . C53A C 0.9695(8) 1.0761(9) 0.8920(8) 0.098(4) Uani 1 1 d . . . H55 H 0.9509 1.1037 0.9352 0.118 Uiso 1 1 calc R . . C52A C 1.0403(8) 1.1013(9) 0.8666(9) 0.101(4) Uani 1 1 d . . . H54 H 1.0704 1.1448 0.8933 0.121 Uiso 1 1 calc R . . C44 C 0.9730(9) 0.7135(9) 0.3430(6) 0.098(4) Uani 1 1 d . . . H44A H 0.9320 0.6923 0.3076 0.147 Uiso 1 1 calc R . . H44B H 1.0190 0.6777 0.3370 0.147 Uiso 1 1 calc R . . H44C H 0.9839 0.7763 0.3326 0.147 Uiso 1 1 calc R . . H39 H 0.801(5) 0.667(5) 0.646(4) 0.04(2) Uiso 1 1 d . . . H10 H 0.149(3) 0.690(4) 0.816(4) 0.015(15) Uiso 1 1 d . . . H62 H 0.233(5) 0.984(7) 0.804(6) 0.07(3) Uiso 1 1 d . . . H7 H 1.025(5) 0.682(5) 0.697(5) 0.02(3) Uiso 1 1 d . . . H61 H 0.788(8) 0.931(9) 0.772(7) 0.12(4) 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 O7 0.044(4) 0.035(4) 0.084(5) 0.005(3) 0.011(3) 0.001(3) O5 0.049(4) 0.040(3) 0.081(4) 0.013(3) 0.008(3) -0.005(3) O4 0.078(4) 0.043(3) 0.047(4) 0.005(3) 0.015(3) -0.005(3) O8 0.039(3) 0.044(3) 0.089(5) -0.011(3) 0.015(3) -0.001(3) O3 0.084(5) 0.040(3) 0.054(4) -0.002(3) 0.016(3) 0.007(3) O6 0.048(4) 0.045(3) 0.096(5) 0.010(3) 0.012(3) -0.007(3) O1 0.067(4) 0.052(4) 0.070(4) -0.006(3) 0.006(3) 0.014(3) O2 0.065(4) 0.056(4) 0.061(4) -0.006(3) 0.015(3) 0.000(3) N4 0.044(4) 0.034(3) 0.072(5) -0.002(3) 0.012(3) 0.000(3) N3 0.044(4) 0.036(4) 0.066(5) -0.005(3) 0.014(3) 0.005(3) N2 0.073(5) 0.042(4) 0.049(4) 0.002(3) 0.013(4) -0.006(3) N1 0.067(5) 0.046(4) 0.049(4) 0.003(3) 0.016(4) -0.011(4) C4 0.053(5) 0.033(4) 0.055(5) -0.004(4) -0.003(4) -0.007(4) C31 0.048(5) 0.033(4) 0.049(5) -0.001(3) 0.002(4) 0.000(3) C2 0.049(5) 0.031(4) 0.049(5) 0.003(3) 0.005(4) 0.001(3) C37 0.038(4) 0.034(4) 0.063(5) -0.002(4) 0.011(4) -0.005(3) C29 0.036(4) 0.036(4) 0.049(5) -0.003(3) 0.004(3) -0.004(3) C30 0.045(5) 0.029(4) 0.057(5) -0.007(3) 0.012(4) -0.002(3) C10 0.056(5) 0.031(4) 0.046(5) 0.000(4) 0.005(4) 0.001(4) C1 0.047(5) 0.047(5) 0.046(5) -0.004(4) 0.002(4) 0.002(4) C38 0.040(4) 0.047(5) 0.055(5) -0.002(4) -0.002(4) -0.002(4) C11 0.053(5) 0.032(4) 0.048(5) 0.000(3) 0.003(4) -0.005(4) C19 0.057(5) 0.035(4) 0.061(6) 0.002(4) 0.018(4) 0.001(4) C43 0.071(6) 0.036(4) 0.067(6) -0.010(4) 0.014(5) -0.003(4) C22 0.058(5) 0.030(4) 0.062(6) 0.004(4) 0.005(4) -0.002(4) C47A 0.041(4) 0.030(4) 0.061(5) 0.001(4) 0.004(4) 0.003(3) C32 0.050(5) 0.045(5) 0.060(5) -0.003(4) -0.003(4) -0.001(4) C18 0.051(5) 0.034(4) 0.058(5) 0.004(4) 0.006(4) -0.002(4) C36 0.056(6) 0.047(5) 0.066(6) 0.000(4) 0.006(4) 0.007(4) C45 0.041(5) 0.037(4) 0.062(5) 0.002(4) 0.010(4) 0.000(4) C16 0.061(6) 0.037(4) 0.061(6) 0.000(4) 0.014(4) 0.001(4) C3 0.046(5) 0.034(4) 0.058(5) -0.001(4) 0.005(4) -0.004(3) C39 0.073(6) 0.043(5) 0.064(6) -0.001(4) 0.010(5) 0.011(4) C46A 0.048(5) 0.034(4) 0.059(5) 0.001(4) 0.009(4) 0.001(4) C49A 0.056(5) 0.031(4) 0.063(6) -0.005(4) 0.008(4) 0.004(4) C15 0.063(6) 0.043(5) 0.069(6) -0.001(4) 0.011(5) -0.010(4) C28 0.047(5) 0.034(4) 0.065(6) 0.003(4) 0.003(4) -0.004(4) C5 0.055(5) 0.045(5) 0.067(6) 0.005(4) -0.007(5) -0.009(4) C20 0.054(5) 0.046(5) 0.056(5) -0.003(4) 0.007(4) -0.006(4) C42 0.085(7) 0.048(5) 0.072(7) -0.016(5) 0.019(5) -0.004(5) C50A 0.067(6) 0.044(5) 0.102(8) -0.009(5) 0.026(6) -0.002(5) C9 0.074(6) 0.038(5) 0.069(6) -0.002(4) -0.003(5) -0.002(4) C12 0.055(6) 0.045(5) 0.080(7) 0.016(5) 0.008(5) -0.002(4) C40 0.079(7) 0.058(6) 0.062(6) 0.005(5) 0.013(5) -0.004(5) C6 0.064(6) 0.055(6) 0.088(8) -0.005(5) -0.004(5) 0.008(5) C14 0.046(5) 0.060(6) 0.075(6) 0.012(5) -0.003(4) -0.007(4) C23 0.088(7) 0.065(6) 0.059(6) -0.007(5) 0.023(5) -0.021(6) C41 0.070(6) 0.058(6) 0.057(6) -0.010(5) 0.008(5) -0.005(5) C48A 0.050(5) 0.054(5) 0.085(7) -0.010(5) 0.016(5) 0.014(4) C33 0.077(7) 0.045(5) 0.057(6) 0.002(4) 0.004(5) -0.007(5) C21 0.078(7) 0.068(6) 0.051(5) 0.007(5) 0.008(5) -0.016(5) C13 0.058(6) 0.055(6) 0.105(8) 0.026(6) 0.000(6) 0.007(5) C27 0.109(9) 0.048(5) 0.075(7) -0.012(5) 0.043(6) -0.020(5) C24 0.081(7) 0.061(6) 0.087(8) -0.018(6) 0.024(6) -0.030(5) C54A 0.080(7) 0.061(6) 0.099(8) -0.021(6) 0.028(6) -0.018(6) C35 0.071(7) 0.047(5) 0.079(7) -0.005(5) -0.004(5) 0.018(5) C8 0.099(8) 0.048(6) 0.071(7) 0.004(5) -0.021(6) -0.005(6) C25 0.100(8) 0.045(5) 0.094(9) -0.017(6) 0.018(7) -0.026(6) C26 0.138(11) 0.060(7) 0.082(8) -0.023(6) 0.035(7) -0.020(7) C7 0.083(8) 0.051(6) 0.090(8) 0.004(6) -0.020(6) 0.009(5) C34 0.082(7) 0.046(5) 0.067(6) 0.007(5) -0.005(5) 0.014(5) C51A 0.073(7) 0.042(6) 0.156(12) -0.014(7) 0.023(7) -0.010(5) C17 0.058(6) 0.088(8) 0.111(9) 0.026(7) 0.006(6) -0.004(6) C53A 0.107(10) 0.086(9) 0.104(10) -0.044(7) 0.028(8) -0.024(7) C52A 0.089(9) 0.071(8) 0.143(12) -0.036(8) 0.011(8) -0.022(7) C44 0.141(12) 0.089(9) 0.066(7) -0.014(6) 0.024(7) -0.012(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O7 C30 1.310(10) . ? O5 C32 1.366(10) . ? O5 C28 1.393(10) . ? O4 C19 1.260(10) . ? O8 C46A 1.242(9) . ? O3 C3 1.335(10) . ? O6 C28 1.215(10) . ? O1 C5 1.377(11) . ? O1 C1 1.393(10) . ? O2 C1 1.218(10) . ? N4 C46A 1.384(10) . ? N4 N3 1.398(9) . ? N4 C49A 1.409(11) . ? N3 C47A 1.380(10) . ? N2 N1 1.381(10) . ? N2 C19 1.391(10) . ? N2 C22 1.419(11) . ? N1 C20 1.384(11) . ? C4 C5 1.353(13) . ? C4 C9 1.401(12) . ? C4 C3 1.454(11) . ? C31 C32 1.398(12) . ? C31 C36 1.399(12) . ? C31 C30 1.469(11) . ? C2 C3 1.351(11) . ? C2 C1 1.419(11) . ? C2 C10 1.538(11) . ? C37 C38 1.501(12) . ? C37 C45 1.502(11) . ? C37 C29 1.527(11) . ? C29 C30 1.353(11) . ? C29 C28 1.433(11) . ? C10 C18 1.509(11) . ? C10 C11 1.535(11) . ? C38 C43 1.392(12) . ? C38 C39 1.400(12) . ? C11 C12 1.370(12) . ? C11 C16 1.398(11) . ? C19 C18 1.425(12) . ? C43 C42 1.385(13) . ? C22 C27 1.357(13) . ? C22 C23 1.392(12) . ? C47A C45 1.361(11) . ? C47A C48A 1.480(12) . ? C32 C33 1.391(12) . ? C18 C20 1.345(12) . ? C36 C35 1.377(13) . ? C45 C46A 1.459(11) . ? C16 C15 1.397(12) . ? C39 C40 1.371(13) . ? C49A C54A 1.355(13) . ? C49A C50A 1.387(13) . ? C15 C14 1.353(13) . ? C5 C6 1.388(13) . ? C20 C21 1.480(12) . ? C42 C41 1.355(14) . ? C50A C51A 1.425(15) . ? C9 C8 1.378(14) . ? C12 C13 1.404(13) . ? C40 C41 1.375(13) . ? C6 C7 1.419(15) . ? C14 C13 1.362(13) . ? C14 C17 1.537(14) . ? C23 C24 1.371(14) . ? C41 C44 1.498(14) . ? C33 C34 1.385(14) . ? C27 C26 1.415(15) . ? C24 C25 1.327(14) . ? C54A C53A 1.392(15) . ? C35 C34 1.367(14) . ? C8 C7 1.361(15) . ? C25 C26 1.356(15) . ? C51A C52A 1.372(17) . ? C53A C52A 1.370(17) . ? 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 C32 O5 C28 121.2(6) . . ? C5 O1 C1 120.5(7) . . ? C46A N4 N3 108.5(6) . . ? C46A N4 C49A 129.2(7) . . ? N3 N4 C49A 120.0(6) . . ? C47A N3 N4 108.3(6) . . ? N1 N2 C19 108.4(7) . . ? N1 N2 C22 121.2(7) . . ? C19 N2 C22 129.5(7) . . ? N2 N1 C20 107.8(7) . . ? C5 C4 C9 118.5(8) . . ? C5 C4 C3 118.7(8) . . ? C9 C4 C3 122.8(8) . . ? C32 C31 C36 119.3(8) . . ? C32 C31 C30 117.2(7) . . ? C36 C31 C30 123.3(7) . . ? C3 C2 C1 119.7(7) . . ? C3 C2 C10 124.1(7) . . ? C1 C2 C10 116.2(7) . . ? C38 C37 C45 113.3(6) . . ? C38 C37 C29 115.1(6) . . ? C45 C37 C29 111.6(7) . . ? C30 C29 C28 121.8(7) . . ? C30 C29 C37 123.4(7) . . ? C28 C29 C37 114.8(7) . . ? O7 C30 C29 126.7(8) . . ? O7 C30 C31 114.0(7) . . ? C29 C30 C31 119.2(7) . . ? C18 C10 C11 113.0(6) . . ? C18 C10 C2 112.8(7) . . ? C11 C10 C2 115.7(7) . . ? O2 C1 O1 114.2(7) . . ? O2 C1 C2 126.7(8) . . ? O1 C1 C2 119.2(7) . . ? C43 C38 C39 114.7(8) . . ? C43 C38 C37 122.6(8) . . ? C39 C38 C37 122.4(7) . . ? C12 C11 C16 116.0(8) . . ? C12 C11 C10 122.4(7) . . ? C16 C11 C10 121.5(7) . . ? O4 C19 N2 123.0(8) . . ? O4 C19 C18 130.9(8) . . ? N2 C19 C18 106.1(7) . . ? C42 C43 C38 121.8(8) . . ? C27 C22 C23 120.4(8) . . ? C27 C22 N2 119.3(8) . . ? C23 C22 N2 120.2(8) . . ? C45 C47A N3 109.4(7) . . ? C45 C47A C48A 129.8(8) . . ? N3 C47A C48A 120.8(7) . . ? O5 C32 C33 117.0(8) . . ? O5 C32 C31 122.0(8) . . ? C33 C32 C31 121.0(8) . . ? C20 C18 C19 108.3(7) . . ? C20 C18 C10 127.9(8) . . ? C19 C18 C10 123.8(8) . . ? C35 C36 C31 119.2(9) . . ? C47A C45 C46A 107.4(7) . . ? C47A C45 C37 128.1(7) . . ? C46A C45 C37 124.4(7) . . ? C15 C16 C11 120.9(8) . . ? O3 C3 C2 124.5(7) . . ? O3 C3 C4 115.5(7) . . ? C2 C3 C4 120.0(7) . . ? C40 C39 C38 122.6(8) . . ? O8 C46A N4 125.2(7) . . ? O8 C46A C45 128.7(7) . . ? N4 C46A C45 106.0(7) . . ? C54A C49A C50A 121.6(9) . . ? C54A C49A N4 120.5(8) . . ? C50A C49A N4 117.9(8) . . ? C14 C15 C16 121.8(8) . . ? O6 C28 O5 113.9(7) . . ? O6 C28 C29 128.2(8) . . ? O5 C28 C29 117.9(7) . . ? C4 C5 O1 121.2(8) . . ? C4 C5 C6 124.1(9) . . ? O1 C5 C6 114.6(9) . . ? C18 C20 N1 109.2(8) . . ? C18 C20 C21 130.1(8) . . ? N1 C20 C21 120.6(8) . . ? C41 C42 C43 122.3(9) . . ? C49A C50A C51A 117.0(10) . . ? C8 C9 C4 119.3(9) . . ? C11 C12 C13 122.3(8) . . ? C39 C40 C41 121.6(9) . . ? C5 C6 C7 115.9(10) . . ? C15 C14 C13 118.3(9) . . ? C15 C14 C17 123.8(9) . . ? C13 C14 C17 117.8(9) . . ? C24 C23 C22 119.1(9) . . ? C42 C41 C40 117.0(9) . . ? C42 C41 C44 122.2(9) . . ? C40 C41 C44 120.7(10) . . ? C34 C33 C32 118.0(9) . . ? C14 C13 C12 120.5(9) . . ? C22 C27 C26 118.2(9) . . ? C25 C24 C23 121.2(10) . . ? C49A C54A C53A 120.3(10) . . ? C34 C35 C36 120.8(9) . . ? C7 C8 C9 121.4(10) . . ? C24 C25 C26 120.8(10) . . ? C25 C26 C27 120.2(10) . . ? C8 C7 C6 120.6(10) . . ? C35 C34 C33 121.6(9) . . ? C52A C51A C50A 121.2(11) . . ? C52A C53A C54A 120.3(11) . . ? C53A C52A C51A 119.5(11) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.03 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.400 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.097