# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Chao Chen' _publ_contact_author_email CHENCHAONCU@163.COM _publ_section_title ; Supramolecular assembly of [H(4-n)BPTC]n- with pipzH2+: 1D negative charged rectangular tube and neutral zigzag chain ; loop_ _publ_author_name 'Chao Chen.' 'Shengjun Deng.' 'Xuejin Mao.' 'Weiming Xiao.' 'Ning Zhang.' # Attachment 'revised-11.CIF' # Attachment '749742.cif' data_1 #TrackingRef 'revised-11.CIF' _database_code_depnum_ccdc_archive 'CCDC 749742' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C24 H42 N4 O14' _chemical_formula_sum 'C24 H42 N4 O14' _chemical_formula_weight 610.62 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 7.260(3) _cell_length_b 12.744(6) _cell_length_c 16.409(8) _cell_angle_alpha 75.833(7) _cell_angle_beta 88.378(7) _cell_angle_gamma 87.605(7) _cell_volume 1470.4(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6912 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.06 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.114 _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 'Bruker SMART CCD diffractometer' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13657 _diffrn_reflns_av_R_equivalents 0.0591 _diffrn_reflns_av_sigmaI/netI 0.1131 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.06 _reflns_number_total 6912 _reflns_number_gt 3247 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.1333P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6912 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1637 _refine_ls_R_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.2650 _refine_ls_wR_factor_gt 0.2197 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.9820(5) -0.1650(3) 0.4025(2) 0.0308(9) Uani 1 1 d . . . C2 C 0.8503(5) -0.2026(3) 0.3573(2) 0.0300(8) Uani 1 1 d . . . C3 C 0.7106(5) -0.1311(3) 0.3183(2) 0.0313(9) Uani 1 1 d . . . H3A H 0.6245 -0.1559 0.2872 0.038 Uiso 1 1 calc R . . C4 C 0.6951(5) -0.0238(3) 0.3241(2) 0.0312(9) Uani 1 1 d . . . C5 C 0.5452(5) 0.0504(3) 0.2821(2) 0.0308(9) Uani 1 1 d . . . C6 C 0.3687(5) 0.0150(3) 0.2787(3) 0.0346(9) Uani 1 1 d . . . H6A H 0.3429 -0.0569 0.3031 0.042 Uiso 1 1 calc R . . C7 C 0.2306(5) 0.0852(3) 0.2395(3) 0.0355(9) Uani 1 1 d . . . H7A H 0.1137 0.0592 0.2368 0.043 Uiso 1 1 calc R . . C8 C 0.2611(5) 0.1930(3) 0.2043(2) 0.0295(8) Uani 1 1 d . . . C9 C 0.4400(5) 0.2302(3) 0.2061(2) 0.0281(8) Uani 1 1 d . . . C10 C 0.5789(5) 0.1586(3) 0.2445(2) 0.0300(8) Uani 1 1 d . . . H10A H 0.6974 0.1834 0.2452 0.036 Uiso 1 1 calc R . . C11 C 0.8275(5) 0.0115(3) 0.3703(3) 0.0369(9) Uani 1 1 d . . . H11A H 0.8211 0.0826 0.3754 0.044 Uiso 1 1 calc R . . C12 C 0.9680(5) -0.0580(3) 0.4087(2) 0.0345(9) Uani 1 1 d . . . H12A H 1.0548 -0.0328 0.4393 0.041 Uiso 1 1 calc R . . C13 C 1.1439(5) -0.2327(3) 0.4443(3) 0.0345(9) Uani 1 1 d . . . C14 C 0.8461(5) -0.3186(3) 0.3540(2) 0.0304(8) Uani 1 1 d . . . C15 C 0.1022(5) 0.2693(4) 0.1708(3) 0.0364(9) Uani 1 1 d . . . C16 C 0.4880(5) 0.3463(3) 0.1686(2) 0.0313(9) Uani 1 1 d . . . C17 C 0.2275(5) 0.2827(4) 0.3952(3) 0.0389(10) Uani 1 1 d . . . H17A H 0.2293 0.2937 0.3346 0.047 Uiso 1 1 calc R . . H17B H 0.1392 0.2277 0.4186 0.047 Uiso 1 1 calc R . . C18 C 0.4158(5) 0.2440(3) 0.4284(3) 0.0377(10) Uani 1 1 d . . . H18A H 0.4112 0.2250 0.4894 0.045 Uiso 1 1 calc R . . H18B H 0.4547 0.1799 0.4097 0.045 Uiso 1 1 calc R . . C19 C 0.4914(6) 0.4302(4) 0.4212(3) 0.0416(10) Uani 1 1 d . . . H19A H 0.5810 0.4850 0.3996 0.050 Uiso 1 1 calc R . . H19B H 0.4870 0.4174 0.4819 0.050 Uiso 1 1 calc R . . C20 C 0.3049(6) 0.4711(3) 0.3870(3) 0.0426(10) Uani 1 1 d . . . H20A H 0.2673 0.5356 0.4054 0.051 Uiso 1 1 calc R . . H20B H 0.3107 0.4898 0.3260 0.051 Uiso 1 1 calc R . . C21 C 0.5979(7) -0.0169(4) 0.0770(3) 0.0558(13) Uani 1 1 d . . . H21A H 0.6344 0.0092 0.1248 0.067 Uiso 1 1 calc R . . H21B H 0.6519 -0.0892 0.0828 0.067 Uiso 1 1 calc R . . C22 C 0.6668(6) 0.0554(4) -0.0015(3) 0.0420(10) Uani 1 1 d . . . H22A H 0.8004 0.0555 -0.0008 0.050 Uiso 1 1 calc R . . H22B H 0.6201 0.1288 -0.0049 0.050 Uiso 1 1 calc R . . C23 C 0.8421(5) 0.4555(3) 0.0479(2) 0.0310(9) Uani 1 1 d . . . H23A H 0.7096 0.4543 0.0574 0.037 Uiso 1 1 calc R . . H23B H 0.8985 0.4000 0.0924 0.037 Uiso 1 1 calc R . . C24 C 0.8870(6) 0.4306(4) -0.0343(3) 0.0520(12) Uani 1 1 d . . . H24A H 0.8202 0.4811 -0.0785 0.062 Uiso 1 1 calc R . . H24B H 0.8500 0.3580 -0.0332 0.062 Uiso 1 1 calc R . . N1 N 0.5501(4) 0.3300(3) 0.3981(2) 0.0349(8) Uani 1 1 d . . . H1A H 0.6610 0.3072 0.4203 0.042 Uiso 1 1 calc R . . H1B H 0.5622 0.3429 0.3418 0.042 Uiso 1 1 calc R . . N2 N 0.1686(4) 0.3857(3) 0.4173(2) 0.0377(8) Uani 1 1 d . . . H2A H 0.0585 0.4088 0.3943 0.045 Uiso 1 1 calc R . . H2B H 0.1550 0.3737 0.4735 0.045 Uiso 1 1 calc R . . O1 O 0.8084(4) -0.3390(2) 0.28523(18) 0.0472(8) Uani 1 1 d . . . O2 O 0.8752(4) -0.3899(2) 0.41937(18) 0.0473(8) Uani 1 1 d . . . O3 O 1.2575(4) -0.2719(3) 0.4013(2) 0.0527(8) Uani 1 1 d . . . O4 O 1.1556(4) -0.2392(3) 0.52161(18) 0.0470(8) Uani 1 1 d . . . O5 O -0.0157(4) 0.2395(3) 0.1282(2) 0.0557(9) Uani 1 1 d . . . O6 O 0.0953(4) 0.3586(3) 0.1882(2) 0.0503(8) Uani 1 1 d . . . O7 O 0.4808(4) 0.3825(2) 0.09055(16) 0.0371(7) Uani 1 1 d . . . O8 O 0.5408(4) 0.3985(2) 0.21808(18) 0.0483(8) Uani 1 1 d . . . O9 O 0.8861(4) 0.4405(2) 0.30822(18) 0.0447(7) Uani 1 1 d . . . O10 O 0.5439(4) 0.6161(2) 0.18228(19) 0.0500(8) Uani 1 1 d . . . O11 O 0.2947(5) 0.7649(3) 0.2307(2) 0.0662(10) Uani 1 1 d . . . O12 O 0.0189(5) 0.1098(3) 0.0196(2) 0.0670(10) Uani 1 1 d . . . O13 O 0.4931(6) 0.2535(3) 0.9802(2) 0.0698(11) Uani 1 1 d . . . O14 O -0.0265(7) 0.7774(4) 0.1417(3) 0.1058(16) Uani 1 1 d . . . N4 N 0.6091(7) 0.0207(5) -0.0763(3) 0.0872(16) Uani 1 1 d . . . H4A H 0.6596 -0.0452 -0.0755 0.105 Uiso 1 1 calc R . . H4B H 0.6493 0.0674 -0.1232 0.105 Uiso 1 1 calc R . . N3 N 0.9065(6) 0.5607(4) 0.0519(3) 0.0796(15) Uani 1 1 d . . . H3B H 0.8806 0.5715 0.1032 0.096 Uiso 1 1 calc R . . H3C H 0.8460 0.6129 0.0140 0.096 Uiso 1 1 calc R . . H121 H 0.0410 0.1602 -0.0360 0.096 Uiso 1 1 d R . . H122 H 0.0025 0.1758 0.0525 0.096 Uiso 1 1 d R . . H111 H 0.2612 0.7435 0.2904 0.096 Uiso 1 1 d R . . H112 H 0.3678 0.6990 0.2245 0.096 Uiso 1 1 d R . . H91 H 0.9297 0.4358 0.2571 0.096 Uiso 1 1 d R . . H92 H 0.8635 0.5103 0.2955 0.096 Uiso 1 1 d R . . H141 H -0.0021 0.8248 0.1552 0.096 Uiso 1 1 d R . . H142 H 0.0508 0.7273 0.1527 0.096 Uiso 1 1 d R . . H101 H 0.5498 0.5457 0.1919 0.096 Uiso 1 1 d R . . H102 H 0.6318 0.6325 0.2225 0.096 Uiso 1 1 d R . . H131 H 0.4814 0.3031 0.9252 0.096 Uiso 1 1 d R . . H132 H 0.4750 0.3034 1.0216 0.096 Uiso 1 1 d 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 C1 0.032(2) 0.029(2) 0.029(2) -0.0030(17) -0.0012(15) 0.0010(16) C2 0.033(2) 0.030(2) 0.0259(19) -0.0055(16) -0.0050(15) 0.0030(16) C3 0.035(2) 0.029(2) 0.031(2) -0.0070(17) -0.0081(16) 0.0005(16) C4 0.032(2) 0.032(2) 0.029(2) -0.0054(17) -0.0044(16) 0.0020(17) C5 0.034(2) 0.029(2) 0.032(2) -0.0109(17) -0.0022(16) 0.0023(16) C6 0.035(2) 0.024(2) 0.043(2) -0.0025(18) 0.0008(17) -0.0034(16) C7 0.0280(19) 0.036(2) 0.041(2) -0.0063(19) -0.0020(17) -0.0035(17) C8 0.0298(19) 0.031(2) 0.0267(19) -0.0046(16) -0.0023(15) 0.0007(16) C9 0.031(2) 0.026(2) 0.0273(19) -0.0068(16) 0.0016(15) -0.0012(15) C10 0.0262(18) 0.030(2) 0.034(2) -0.0086(17) -0.0031(15) -0.0025(16) C11 0.042(2) 0.030(2) 0.041(2) -0.0117(18) -0.0098(18) 0.0007(18) C12 0.032(2) 0.038(2) 0.035(2) -0.0115(18) -0.0086(16) 0.0003(17) C13 0.030(2) 0.034(2) 0.039(2) -0.0057(19) -0.0044(17) -0.0010(17) C14 0.034(2) 0.030(2) 0.029(2) -0.0082(17) -0.0052(16) -0.0001(16) C15 0.033(2) 0.038(3) 0.033(2) 0.0008(19) 0.0000(17) 0.0042(18) C16 0.0291(19) 0.031(2) 0.032(2) -0.0046(17) -0.0011(16) -0.0009(16) C17 0.034(2) 0.047(3) 0.043(2) -0.023(2) 0.0004(18) -0.0060(19) C18 0.039(2) 0.037(2) 0.037(2) -0.0079(19) -0.0002(18) 0.0013(18) C19 0.038(2) 0.042(3) 0.050(3) -0.018(2) -0.0016(19) -0.0053(19) C20 0.041(2) 0.031(2) 0.052(3) -0.006(2) 0.005(2) 0.0013(19) C21 0.064(3) 0.060(3) 0.044(3) -0.013(2) -0.007(2) -0.003(3) C22 0.043(2) 0.044(3) 0.039(2) -0.010(2) 0.0009(19) -0.004(2) C23 0.0196(17) 0.025(2) 0.038(2) 0.0117(17) 0.0058(15) 0.0017(15) C24 0.034(2) 0.046(3) 0.068(3) 0.002(2) -0.004(2) -0.002(2) N1 0.0282(16) 0.041(2) 0.0358(18) -0.0095(16) -0.0051(14) 0.0028(15) N2 0.0311(17) 0.049(2) 0.0326(18) -0.0088(16) -0.0052(14) 0.0017(16) O1 0.069(2) 0.0342(17) 0.0406(17) -0.0121(14) -0.0171(15) 0.0039(15) O2 0.075(2) 0.0278(17) 0.0379(17) -0.0060(14) -0.0059(15) 0.0005(15) O3 0.0475(18) 0.061(2) 0.0509(19) -0.0201(17) -0.0042(15) 0.0196(16) O4 0.0374(16) 0.065(2) 0.0364(17) -0.0105(15) -0.0096(13) 0.0128(15) O5 0.0462(18) 0.059(2) 0.062(2) -0.0130(17) -0.0233(16) 0.0062(16) O6 0.0505(19) 0.0377(19) 0.059(2) -0.0072(16) -0.0001(15) 0.0123(14) O7 0.0452(17) 0.0340(16) 0.0298(15) -0.0035(12) 0.0014(12) -0.0032(13) O8 0.070(2) 0.0358(17) 0.0418(17) -0.0113(14) -0.0124(15) -0.0150(15) O9 0.0482(17) 0.0436(18) 0.0438(17) -0.0144(14) -0.0107(13) 0.0091(14) O10 0.063(2) 0.0365(18) 0.0513(19) -0.0101(15) -0.0116(15) -0.0029(15) O11 0.076(2) 0.065(2) 0.056(2) -0.0136(18) 0.0045(18) 0.0103(19) O12 0.066(2) 0.058(2) 0.080(3) -0.023(2) -0.0110(19) -0.0014(18) O13 0.109(3) 0.051(2) 0.050(2) -0.0145(17) -0.012(2) 0.008(2) O14 0.099(3) 0.144(5) 0.068(3) -0.009(3) -0.011(2) -0.021(3) N4 0.085(4) 0.108(4) 0.065(3) -0.014(3) 0.007(3) -0.006(3) N3 0.057(3) 0.096(4) 0.080(3) -0.014(3) 0.003(2) 0.019(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 C12 1.390(5) . ? C1 C2 1.395(5) . ? C1 C13 1.506(5) . ? C2 C3 1.394(5) . ? C2 C14 1.494(5) . ? C3 C4 1.394(5) . ? C3 H3A 0.9300 . ? C4 C11 1.395(5) . ? C4 C5 1.480(5) . ? C5 C6 1.383(5) . ? C5 C10 1.395(5) . ? C6 C7 1.379(5) . ? C6 H6A 0.9300 . ? C7 C8 1.378(6) . ? C7 H7A 0.9300 . ? C8 C9 1.405(5) . ? C8 C15 1.503(5) . ? C9 C10 1.387(5) . ? C9 C16 1.508(5) . ? C10 H10A 0.9300 . ? C11 C12 1.382(5) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 O3 1.238(5) . ? C13 O4 1.256(5) . ? C14 O2 1.241(5) . ? C14 O1 1.259(4) . ? C15 O6 1.238(5) . ? C15 O5 1.247(5) . ? C16 O8 1.247(5) . ? C16 O7 1.252(5) . ? C17 N2 1.489(5) . ? C17 C18 1.504(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N1 1.481(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 N1 1.463(5) . ? C19 C20 1.503(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 N2 1.486(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.477(6) . ? C21 N4 1.506(7) 2_655 ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N4 1.478(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 N3 1.454(6) . ? C23 C24 1.485(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 N3 1.523(6) 2_765 ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? O9 H91 0.9027 . ? O9 H92 0.8719 . ? O10 H101 0.8713 . ? O10 H102 0.9949 . ? O11 H111 0.9775 . ? O11 H112 0.9997 . ? O12 H121 0.9917 . ? O12 H122 1.1063 . ? O13 H131 0.9692 . ? O13 H132 1.0409 . ? O14 H141 0.7233 . ? O14 H142 0.8214 . ? N4 C21 1.506(7) 2_655 ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? N3 C24 1.523(6) 2_765 ? N3 H3B 0.9000 . ? N3 H3C 0.9000 . ? 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 C12 C1 C2 119.1(3) . . ? C12 C1 C13 116.9(3) . . ? C2 C1 C13 124.0(4) . . ? C3 C2 C1 118.9(4) . . ? C3 C2 C14 118.6(3) . . ? C1 C2 C14 122.3(3) . . ? C4 C3 C2 122.5(3) . . ? C4 C3 H3A 118.8 . . ? C2 C3 H3A 118.8 . . ? C3 C4 C11 117.4(3) . . ? C3 C4 C5 121.4(3) . . ? C11 C4 C5 121.2(4) . . ? C6 C5 C10 118.1(4) . . ? C6 C5 C4 121.4(3) . . ? C10 C5 C4 120.5(3) . . ? C7 C6 C5 120.6(4) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C8 C7 C6 121.7(4) . . ? C8 C7 H7A 119.1 . . ? C6 C7 H7A 119.1 . . ? C7 C8 C9 118.5(3) . . ? C7 C8 C15 119.9(3) . . ? C9 C8 C15 121.4(3) . . ? C10 C9 C8 119.4(3) . . ? C10 C9 C16 118.0(3) . . ? C8 C9 C16 122.6(3) . . ? C9 C10 C5 121.6(3) . . ? C9 C10 H10A 119.2 . . ? C5 C10 H10A 119.2 . . ? C12 C11 C4 120.8(4) . . ? C12 C11 H11A 119.6 . . ? C4 C11 H11A 119.6 . . ? C11 C12 C1 121.2(4) . . ? C11 C12 H12A 119.4 . . ? C1 C12 H12A 119.4 . . ? O3 C13 O4 125.4(4) . . ? O3 C13 C1 119.6(4) . . ? O4 C13 C1 114.9(4) . . ? O2 C14 O1 123.2(4) . . ? O2 C14 C2 118.7(3) . . ? O1 C14 C2 118.0(3) . . ? O6 C15 O5 123.6(4) . . ? O6 C15 C8 117.4(4) . . ? O5 C15 C8 118.9(4) . . ? O8 C16 O7 124.3(4) . . ? O8 C16 C9 116.7(3) . . ? O7 C16 C9 118.9(3) . . ? N2 C17 C18 111.3(3) . . ? N2 C17 H17A 109.4 . . ? C18 C17 H17A 109.4 . . ? N2 C17 H17B 109.4 . . ? C18 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? N1 C18 C17 110.1(3) . . ? N1 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? N1 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? N1 C19 C20 111.7(3) . . ? N1 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? N1 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? N2 C20 C19 109.4(3) . . ? N2 C20 H20A 109.8 . . ? C19 C20 H20A 109.8 . . ? N2 C20 H20B 109.8 . . ? C19 C20 H20B 109.8 . . ? H20A C20 H20B 108.2 . . ? C22 C21 N4 110.3(4) . 2_655 ? C22 C21 H21A 109.6 . . ? N4 C21 H21A 109.6 2_655 . ? C22 C21 H21B 109.6 . . ? N4 C21 H21B 109.6 2_655 . ? H21A C21 H21B 108.1 . . ? C21 C22 N4 111.5(4) . . ? C21 C22 H22A 109.3 . . ? N4 C22 H22A 109.3 . . ? C21 C22 H22B 109.3 . . ? N4 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? N3 C23 C24 112.1(3) . . ? N3 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? N3 C23 H23B 109.2 . . ? C24 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C23 C24 N3 109.4(4) . 2_765 ? C23 C24 H24A 109.8 . . ? N3 C24 H24A 109.8 2_765 . ? C23 C24 H24B 109.8 . . ? N3 C24 H24B 109.8 2_765 . ? H24A C24 H24B 108.2 . . ? C19 N1 C18 111.4(3) . . ? C19 N1 H1A 109.4 . . ? C18 N1 H1A 109.4 . . ? C19 N1 H1B 109.4 . . ? C18 N1 H1B 109.4 . . ? H1A N1 H1B 108.0 . . ? C20 N2 C17 111.5(3) . . ? C20 N2 H2A 109.3 . . ? C17 N2 H2A 109.3 . . ? C20 N2 H2B 109.3 . . ? C17 N2 H2B 109.3 . . ? H2A N2 H2B 108.0 . . ? H91 O9 H92 97.0 . . ? H101 O10 H102 104.2 . . ? H111 O11 H112 100.4 . . ? H121 O12 H122 93.5 . . ? H131 O13 H132 103.8 . . ? H141 O14 H142 113.8 . . ? C22 N4 C21 110.1(4) . 2_655 ? C22 N4 H4A 109.6 . . ? C21 N4 H4A 109.6 2_655 . ? C22 N4 H4B 109.6 . . ? C21 N4 H4B 109.6 2_655 . ? H4A N4 H4B 108.2 . . ? C23 N3 C24 111.8(4) . 2_765 ? C23 N3 H3B 109.3 . . ? C24 N3 H3B 109.3 2_765 . ? C23 N3 H3C 109.3 . . ? C24 N3 H3C 109.3 2_765 . ? H3B N3 H3C 107.9 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.558 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.076 # Attachment 'revised-21.CIF' # Attachment '749743.cif' data_2 #TrackingRef 'revised-21.CIF' _database_code_depnum_ccdc_archive 'CCDC 749743' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C20 H24 N2 O10' _chemical_formula_sum 'C20 H24 N2 O10' _chemical_formula_weight 452.41 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 6.2017(9) _cell_length_b 8.3441(13) _cell_length_c 9.6508(14) _cell_angle_alpha 91.155(2) _cell_angle_beta 93.378(2) _cell_angle_gamma 94.221(2) _cell_volume 497.04(13) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2409 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 238 _exptl_absorpt_coefficient_mu 0.123 _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 'Bruker SMART CCD diffractometer' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4756 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2409 _reflns_number_gt 1516 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0966P)^2^+0.4355P] 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 2409 _refine_ls_number_parameters 191 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1187 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.2184 _refine_ls_wR_factor_gt 0.1883 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.098 _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 0.7433(5) 0.1346(4) 0.5675(3) 0.0286(7) Uani 1 1 d . . . C2 C 0.5989(5) 0.0442(4) 0.4760(3) 0.0255(6) Uani 1 1 d . . . C3 C 0.6501(5) 0.0378(4) 0.3374(3) 0.0324(7) Uani 1 1 d . . . C4 C 0.8370(5) 0.1194(4) 0.2961(3) 0.0319(7) Uani 1 1 d . . . C5 C 0.9797(5) 0.2123(3) 0.3876(3) 0.0262(7) Uani 1 1 d . . . C6 C 0.9313(5) 0.2203(3) 0.5285(3) 0.0261(7) Uani 1 1 d . . . C7 C 1.0578(5) 0.3113(4) 0.6480(3) 0.0299(7) Uani 1 1 d . . . C8 C 1.1718(5) 0.2930(4) 0.3190(3) 0.0324(7) Uani 1 1 d . . . C9 C 0.5571(6) 0.3898(4) 0.8952(4) 0.0378(8) Uani 1 1 d . . . C10 C 0.3051(6) 0.5791(5) 0.9726(4) 0.0381(8) Uani 1 1 d . . . H1 H 0.874(6) 0.109(5) 0.198(4) 0.045(10) Uiso 1 1 d . . . H2 H 0.559(6) -0.031(5) 0.266(4) 0.046(11) Uiso 1 1 d . . . H3 H 0.706(5) 0.139(4) 0.661(4) 0.030(9) Uiso 1 1 d . . . H4 H 1.249(9) 0.413(6) 0.513(3) 0.096(18) Uiso 1 1 d D . . H5 H 0.232(7) 0.673(5) 0.952(4) 0.049(11) Uiso 1 1 d . . . H6 H 0.209(7) 0.481(5) 0.975(4) 0.056(12) Uiso 1 1 d . . . H7 H 0.643(7) 0.370(5) 0.824(5) 0.058(12) Uiso 1 1 d . . . H8 H 0.447(6) 0.297(4) 0.903(4) 0.032(9) Uiso 1 1 d . . . H9 H 0.354(5) 0.987(5) 0.017(4) 0.039 Uiso 1 1 d D . . H10 H 0.196(6) 1.059(5) 0.107(4) 0.039 Uiso 1 1 d . . . H11 H 0.535(7) 0.623(5) 0.840(4) 0.054(12) Uiso 1 1 d . . . H12 H 0.341(8) 0.506(6) 0.771(5) 0.072(14) Uiso 1 1 d . . . N1 N 0.4388(5) 0.5332(4) 0.8589(3) 0.0344(7) Uani 1 1 d . . . O1 O 1.2108(4) 0.4160(3) 0.6220(3) 0.0489(8) Uani 1 1 d D . . O2 O 1.0121(4) 0.2876(3) 0.7674(3) 0.0468(7) Uani 1 1 d . . . O3 O 1.2027(4) 0.2567(3) 0.1978(3) 0.0482(7) Uani 1 1 d . . . O4 O 1.2984(4) 0.4001(3) 0.3852(3) 0.0500(8) Uani 1 1 d . . . O5 O 0.2295(10) 0.9471(6) 0.0632(5) 0.1211(19) Uani 1 1 d 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 0.0264(16) 0.0345(16) 0.0235(16) -0.0036(13) 0.0017(12) -0.0056(13) C2 0.0207(15) 0.0287(15) 0.0259(15) -0.0016(12) 0.0004(11) -0.0050(11) C3 0.0278(17) 0.0407(18) 0.0260(17) -0.0035(14) -0.0025(13) -0.0112(14) C4 0.0315(17) 0.0380(17) 0.0244(16) -0.0002(13) 0.0031(13) -0.0095(13) C5 0.0242(15) 0.0266(14) 0.0269(15) -0.0007(12) 0.0015(12) -0.0037(11) C6 0.0236(15) 0.0269(15) 0.0265(15) -0.0034(12) -0.0002(12) -0.0045(11) C7 0.0243(16) 0.0376(17) 0.0263(16) -0.0047(13) 0.0022(12) -0.0075(13) C8 0.0297(17) 0.0336(16) 0.0323(18) 0.0000(13) 0.0040(13) -0.0096(13) C9 0.040(2) 0.043(2) 0.0304(18) -0.0109(15) 0.0047(15) -0.0001(16) C10 0.0319(19) 0.047(2) 0.0353(19) -0.0023(16) 0.0008(14) 0.0009(16) N1 0.0333(16) 0.0426(16) 0.0253(14) -0.0031(12) 0.0018(12) -0.0097(12) O1 0.0457(16) 0.0626(17) 0.0321(14) -0.0067(12) 0.0007(11) -0.0347(13) O2 0.0444(15) 0.0615(17) 0.0298(13) -0.0112(11) 0.0030(11) -0.0247(12) O3 0.0512(16) 0.0552(16) 0.0355(14) -0.0088(12) 0.0167(12) -0.0238(13) O4 0.0433(15) 0.0635(17) 0.0383(15) -0.0077(12) 0.0092(12) -0.0321(13) O5 0.191(6) 0.083(3) 0.087(4) -0.028(3) -0.031(3) 0.036(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 C1 C2 1.390(4) . ? C1 C6 1.398(4) . ? C1 H3 0.94(3) . ? C2 C3 1.394(4) . ? C2 C2 1.487(6) 2_656 ? C3 C4 1.384(4) . ? C3 H2 1.00(4) . ? C4 C5 1.394(4) . ? C4 H1 0.99(4) . ? C5 C6 1.411(4) . ? C5 C8 1.518(4) . ? C6 C7 1.514(4) . ? C7 O2 1.220(4) . ? C7 O1 1.281(4) . ? C8 O3 1.231(4) . ? C8 O4 1.280(4) . ? C9 N1 1.486(5) . ? C9 C10 1.501(5) 2_667 ? C9 H7 0.91(4) . ? C9 H8 1.00(4) . ? C10 N1 1.475(4) . ? C10 C9 1.501(5) 2_667 ? C10 H5 0.95(4) . ? C10 H6 0.98(4) . ? N1 H11 0.95(4) . ? N1 H12 1.02(5) . ? O1 H4 1.10(2) . ? O4 H4 1.29(2) . ? O5 H9 0.957(19) . ? O5 H10 1.06(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 C6 124.2(3) . . ? C2 C1 H3 116(2) . . ? C6 C1 H3 120(2) . . ? C1 C2 C3 116.9(3) . . ? C1 C2 C2 121.6(3) . 2_656 ? C3 C2 C2 121.5(3) . 2_656 ? C4 C3 C2 120.2(3) . . ? C4 C3 H2 118(2) . . ? C2 C3 H2 122(2) . . ? C3 C4 C5 122.8(3) . . ? C3 C4 H1 119(2) . . ? C5 C4 H1 118(2) . . ? C4 C5 C6 118.0(3) . . ? C4 C5 C8 113.7(3) . . ? C6 C5 C8 128.3(3) . . ? C1 C6 C5 117.9(3) . . ? C1 C6 C7 113.5(3) . . ? C5 C6 C7 128.5(3) . . ? O2 C7 O1 120.3(3) . . ? O2 C7 C6 120.5(3) . . ? O1 C7 C6 119.2(3) . . ? O3 C8 O4 120.1(3) . . ? O3 C8 C5 119.4(3) . . ? O4 C8 C5 120.5(3) . . ? N1 C9 C10 110.5(3) . 2_667 ? N1 C9 H7 107(3) . . ? C10 C9 H7 110(3) 2_667 . ? N1 C9 H8 108(2) . . ? C10 C9 H8 112(2) 2_667 . ? H7 C9 H8 110(3) . . ? N1 C10 C9 110.5(3) . 2_667 ? N1 C10 H5 112(2) . . ? C9 C10 H5 109(2) 2_667 . ? N1 C10 H6 99(3) . . ? C9 C10 H6 113(3) 2_667 . ? H5 C10 H6 114(4) . . ? C10 N1 C9 110.9(3) . . ? C10 N1 H11 108(3) . . ? C9 N1 H11 112(3) . . ? C10 N1 H12 109(3) . . ? C9 N1 H12 109(3) . . ? H11 N1 H12 108(4) . . ? C7 O1 H4 112(3) . . ? C8 O4 H4 111(2) . . ? H9 O5 H10 96(3) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.880 _refine_diff_density_min -0.903 _refine_diff_density_rms 0.076