# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_111010_djd10906139 _database_code_depnum_ccdc_archive 'CCDC 876970' #TrackingRef 'web_deposit_cif_file_0_ChengMa_1334807627.111010_djd10906139.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N O8' _chemical_formula_sum 'C21 H23 N O8' _chemical_formula_weight 417.40 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2700(7) _cell_length_b 13.0333(7) _cell_length_c 13.3502(8) _cell_angle_alpha 104.013(5) _cell_angle_beta 97.803(7) _cell_angle_gamma 103.712(7) _cell_volume 1006.51(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2013 _cell_measurement_theta_min 3.1670 _cell_measurement_theta_max 29.4076 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9567 _exptl_absorpt_correction_T_max 0.9587 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7214 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3683 _reflns_number_gt 2764 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0497P)^2^+0.2918P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3683 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O1 O -0.1527(3) 0.58957(11) 0.92941(13) 0.0561(4) Uani 1 1 d . . . O2 O -0.4307(2) 0.81998(11) 0.60478(11) 0.0473(4) Uani 1 1 d . . . O3 O -0.4230(3) 0.64581(11) 0.57051(13) 0.0689(5) Uani 1 1 d . . . O4 O 0.3435(3) 0.93659(11) 1.08229(11) 0.0545(4) Uani 1 1 d . . . O5 O 0.3117(2) 0.75683(10) 1.04322(11) 0.0473(4) Uani 1 1 d . . . O6 O -0.1283(2) 0.80814(10) 0.96197(11) 0.0418(3) Uani 1 1 d . . . H6 H -0.1800 0.7452 0.9650 0.063 Uiso 1 1 calc R . . O7 O -0.1759(4) 1.23266(16) 0.6754(2) 0.0966(7) Uani 1 1 d . . . O8 O 0.0768(3) 1.27563(15) 0.59034(18) 0.0913(7) Uani 1 1 d . . . N1 N -0.0207(3) 1.21555(15) 0.63604(16) 0.0570(5) Uani 1 1 d . . . C1 C 0.2913(3) 0.70005(15) 0.80970(16) 0.0406(5) Uani 1 1 d . . . H1A H 0.3099 0.7295 0.7503 0.049 Uiso 1 1 calc R . . H1B H 0.4173 0.7406 0.8677 0.049 Uiso 1 1 calc R . . C2 C 0.2753(4) 0.57748(19) 0.7792(2) 0.0690(7) Uani 1 1 d . . . H2A H 0.2057 0.5433 0.7053 0.083 Uiso 1 1 calc R . . H2B H 0.4233 0.5666 0.7914 0.083 Uiso 1 1 calc R . . C3 C 0.1339(4) 0.52870(17) 0.8480(2) 0.0577(6) Uani 1 1 d . . . H3A H 0.0374 0.4559 0.8088 0.069 Uiso 1 1 calc R . . H3B H 0.2283 0.5226 0.9089 0.069 Uiso 1 1 calc R . . C4 C -0.0036(3) 0.60547(15) 0.88185(16) 0.0403(5) Uani 1 1 d . . . C5 C 0.0679(3) 0.70821(13) 0.84296(14) 0.0312(4) Uani 1 1 d . . . C6 C 0.0780(3) 0.81617(14) 0.92583(14) 0.0317(4) Uani 1 1 d . . . C7 C 0.1151(3) 0.91040(14) 0.87634(14) 0.0347(4) Uani 1 1 d . . . H7A H 0.2576 0.9192 0.8540 0.042 Uiso 1 1 calc R . . H7B H 0.1243 0.9779 0.9293 0.042 Uiso 1 1 calc R . . C8 C -0.0702(3) 0.89383(13) 0.78118(14) 0.0323(4) Uani 1 1 d . . . H8 H -0.1915 0.9203 0.8076 0.039 Uiso 1 1 calc R . . C9 C -0.1668(3) 0.77420(13) 0.71872(14) 0.0312(4) Uani 1 1 d . . . C10 C -0.1060(3) 0.69279(14) 0.74666(14) 0.0328(4) Uani 1 1 d . . . H10 H -0.1753 0.6213 0.7040 0.039 Uiso 1 1 calc R . . C11 C -0.3501(3) 0.75114(15) 0.62626(15) 0.0367(4) Uani 1 1 d . . . C12 C -0.6080(5) 0.6188(2) 0.4821(2) 0.0994(12) Uani 1 1 d . . . H12A H -0.5558 0.6477 0.4274 0.149 Uiso 1 1 calc R . . H12B H -0.7228 0.6507 0.5047 0.149 Uiso 1 1 calc R . . H12C H -0.6681 0.5403 0.4556 0.149 Uiso 1 1 calc R . . C13 C 0.2610(3) 0.84523(15) 1.02492(15) 0.0364(4) Uani 1 1 d . . . C14 C 0.4841(4) 0.77642(17) 1.13538(17) 0.0525(6) Uani 1 1 d . . . H14A H 0.4371 0.8097 1.1987 0.063 Uiso 1 1 calc R . . H14B H 0.6222 0.8262 1.1309 0.063 Uiso 1 1 calc R . . C15 C 0.5203(4) 0.66915(19) 1.1392(2) 0.0698(7) Uani 1 1 d . . . H15A H 0.5719 0.6382 1.0774 0.105 Uiso 1 1 calc R . . H15B H 0.3819 0.6199 1.1418 0.105 Uiso 1 1 calc R . . H15C H 0.6307 0.6798 1.2010 0.105 Uiso 1 1 calc R . . C16 C 0.0238(3) 0.96425(14) 0.71257(14) 0.0328(4) Uani 1 1 d . . . C17 C 0.1910(3) 0.94021(15) 0.66093(16) 0.0408(5) Uani 1 1 d . . . H17 H 0.2380 0.8787 0.6657 0.049 Uiso 1 1 calc R . . C18 C 0.2898(3) 1.00510(17) 0.60269(16) 0.0464(5) Uani 1 1 d . . . H18 H 0.4021 0.9872 0.5690 0.056 Uiso 1 1 calc R . . C19 C 0.2221(3) 1.09635(17) 0.59437(16) 0.0465(5) Uani 1 1 d . . . H19 H 0.2876 1.1412 0.5558 0.056 Uiso 1 1 calc R . . C20 C 0.0545(3) 1.11880(14) 0.64498(15) 0.0403(5) Uani 1 1 d . . . C21 C -0.0463(3) 1.05528(14) 0.70417(14) 0.0359(4) Uani 1 1 d . . . H21 H -0.1587 1.0734 0.7376 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0565(9) 0.0444(8) 0.0731(11) 0.0293(8) 0.0203(8) 0.0082(7) O2 0.0449(8) 0.0472(8) 0.0549(9) 0.0196(7) 0.0020(7) 0.0219(6) O3 0.0795(11) 0.0395(8) 0.0671(11) 0.0034(7) -0.0362(9) 0.0189(8) O4 0.0676(10) 0.0399(8) 0.0440(9) 0.0001(7) -0.0063(7) 0.0149(7) O5 0.0542(8) 0.0379(7) 0.0425(8) 0.0106(6) -0.0098(6) 0.0114(6) O6 0.0406(8) 0.0433(7) 0.0493(8) 0.0178(6) 0.0190(6) 0.0161(6) O7 0.1138(17) 0.0866(14) 0.145(2) 0.0745(14) 0.0628(16) 0.0685(13) O8 0.1014(15) 0.0747(12) 0.1317(18) 0.0770(13) 0.0358(13) 0.0327(11) N1 0.0613(12) 0.0475(10) 0.0679(13) 0.0312(10) 0.0036(10) 0.0162(9) C1 0.0355(10) 0.0464(11) 0.0432(12) 0.0122(9) 0.0076(8) 0.0184(8) C2 0.0689(16) 0.0565(14) 0.094(2) 0.0179(13) 0.0279(15) 0.0380(12) C3 0.0678(15) 0.0390(11) 0.0707(16) 0.0171(11) 0.0067(12) 0.0258(11) C4 0.0407(11) 0.0334(10) 0.0428(11) 0.0123(8) -0.0011(9) 0.0070(8) C5 0.0303(9) 0.0286(9) 0.0345(10) 0.0094(7) 0.0029(7) 0.0096(7) C6 0.0315(9) 0.0314(9) 0.0333(10) 0.0096(7) 0.0079(7) 0.0098(7) C7 0.0400(10) 0.0278(9) 0.0344(10) 0.0074(7) 0.0063(8) 0.0083(7) C8 0.0345(9) 0.0302(9) 0.0372(10) 0.0123(7) 0.0112(8) 0.0136(7) C9 0.0289(9) 0.0319(9) 0.0354(10) 0.0109(7) 0.0080(7) 0.0111(7) C10 0.0313(9) 0.0281(9) 0.0363(10) 0.0065(7) 0.0034(8) 0.0078(7) C11 0.0352(10) 0.0360(10) 0.0422(11) 0.0143(8) 0.0073(8) 0.0130(8) C12 0.110(2) 0.0581(15) 0.091(2) 0.0030(14) -0.0653(19) 0.0186(15) C13 0.0394(10) 0.0360(10) 0.0349(11) 0.0100(8) 0.0096(8) 0.0116(8) C14 0.0555(13) 0.0530(12) 0.0417(12) 0.0093(10) -0.0094(10) 0.0165(10) C15 0.0741(17) 0.0536(14) 0.0731(17) 0.0197(12) -0.0190(13) 0.0192(12) C16 0.0361(10) 0.0310(9) 0.0313(10) 0.0092(7) 0.0063(8) 0.0096(8) C17 0.0452(11) 0.0401(10) 0.0452(12) 0.0173(9) 0.0144(9) 0.0190(9) C18 0.0486(12) 0.0558(12) 0.0423(12) 0.0190(10) 0.0179(10) 0.0185(10) C19 0.0496(12) 0.0498(12) 0.0405(12) 0.0228(9) 0.0074(9) 0.0051(10) C20 0.0455(11) 0.0330(10) 0.0405(11) 0.0146(8) -0.0019(9) 0.0092(8) C21 0.0377(10) 0.0337(9) 0.0370(11) 0.0114(8) 0.0044(8) 0.0117(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 O1 C4 1.205(2) . ? O2 C11 1.201(2) . ? O3 C11 1.328(2) . ? O3 C12 1.448(3) . ? O4 C13 1.196(2) . ? O5 C13 1.333(2) . ? O5 C14 1.450(2) . ? O6 C6 1.430(2) . ? O6 H6 0.8200 . ? O7 N1 1.208(3) . ? O8 N1 1.210(2) . ? N1 C20 1.472(3) . ? C1 C2 1.525(3) . ? C1 C5 1.545(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.507(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.498(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.542(2) . ? C5 C10 1.508(2) . ? C5 C6 1.547(2) . ? C6 C7 1.516(2) . ? C6 C13 1.533(3) . ? C7 C8 1.536(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.510(2) . ? C8 C16 1.525(2) . ? C8 H8 0.9800 . ? C9 C10 1.325(2) . ? C9 C11 1.486(3) . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C14 C15 1.480(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C21 1.383(2) . ? C16 C17 1.386(3) . ? C17 C18 1.380(3) . ? C17 H17 0.9300 . ? C18 C19 1.377(3) . ? C18 H18 0.9300 . ? C19 C20 1.374(3) . ? C19 H19 0.9300 . ? C20 C21 1.383(3) . ? C21 H21 0.9300 . ? 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 C11 O3 C12 115.56(16) . . ? C13 O5 C14 116.59(15) . . ? C6 O6 H6 109.5 . . ? O7 N1 O8 122.4(2) . . ? O7 N1 C20 118.82(18) . . ? O8 N1 C20 118.7(2) . . ? C2 C1 C5 105.44(16) . . ? C2 C1 H1A 110.7 . . ? C5 C1 H1A 110.7 . . ? C2 C1 H1B 110.7 . . ? C5 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? C3 C2 C1 106.06(18) . . ? C3 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? C3 C2 H2B 110.5 . . ? C1 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? C4 C3 C2 106.30(17) . . ? C4 C3 H3A 110.5 . . ? C2 C3 H3A 110.5 . . ? C4 C3 H3B 110.5 . . ? C2 C3 H3B 110.5 . . ? H3A C3 H3B 108.7 . . ? O1 C4 C3 126.17(18) . . ? O1 C4 C5 124.16(18) . . ? C3 C4 C5 109.64(17) . . ? C10 C5 C4 106.75(14) . . ? C10 C5 C1 109.35(15) . . ? C4 C5 C1 103.07(15) . . ? C10 C5 C6 108.53(14) . . ? C4 C5 C6 112.79(15) . . ? C1 C5 C6 115.91(14) . . ? O6 C6 C7 107.65(14) . . ? O6 C6 C13 105.73(14) . . ? C7 C6 C13 109.32(14) . . ? O6 C6 C5 110.94(14) . . ? C7 C6 C5 109.50(14) . . ? C13 C6 C5 113.49(14) . . ? C6 C7 C8 113.64(14) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C16 111.50(15) . . ? C9 C8 C7 112.31(14) . . ? C16 C8 C7 108.81(14) . . ? C9 C8 H8 108.0 . . ? C16 C8 H8 108.0 . . ? C7 C8 H8 108.0 . . ? C10 C9 C11 120.86(16) . . ? C10 C9 C8 123.42(16) . . ? C11 C9 C8 115.57(14) . . ? C9 C10 C5 124.40(16) . . ? C9 C10 H10 117.8 . . ? C5 C10 H10 117.8 . . ? O2 C11 O3 122.51(17) . . ? O2 C11 C9 123.76(17) . . ? O3 C11 C9 113.70(15) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O4 C13 O5 123.32(18) . . ? O4 C13 C6 123.93(17) . . ? O5 C13 C6 112.69(15) . . ? O5 C14 C15 108.02(17) . . ? O5 C14 H14A 110.1 . . ? C15 C14 H14A 110.1 . . ? O5 C14 H14B 110.1 . . ? C15 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 118.64(16) . . ? C21 C16 C8 121.60(16) . . ? C17 C16 C8 119.69(16) . . ? C18 C17 C16 121.78(18) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C19 C18 C17 120.02(19) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 117.73(17) . . ? C20 C19 H19 121.1 . . ? C18 C19 H19 121.1 . . ? C19 C20 C21 123.30(18) . . ? C19 C20 N1 118.30(17) . . ? C21 C20 N1 118.40(19) . . ? C16 C21 C20 118.53(18) . . ? C16 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.186 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.042