# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_general _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- CIF_re.cif' _publ_contact_author_name 'Isao Azumaya' _publ_contact_author_address ; Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, JAPAN ; _publ_contact_author_email azumayai@kph.bunri-u.ac.jp _publ_contact_author_phone +81-87-894-5111x6308 _publ_contact_author_fax +81-87-894-0181 loop_ _publ_author_name _publ_author_address H.Masu ; Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, JAPAN ; 'Isao Azumaya' '' K.Katagiri '' H.Kagechika '' A.Tanatani '' #===END data_2d(a0808281mas) _database_code_depnum_ccdc_archive 'CCDC 808148' #TrackingRef '- CIF_re.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H45 N3 O9, 1.5(C2N)' _chemical_formula_sum 'C42 H45 N4.50 O9' _chemical_formula_weight 756.83 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 Hexagonal _symmetry_space_group_name_H-M 'P6(3)/m ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 16.5789(8) _cell_length_b 16.5789(8) _cell_length_c 19.1248(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4552.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 6239 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.56 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1602 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9693 _exptl_absorpt_correction_T_max 0.9693 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 22648 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.17 _reflns_number_total 3351 _reflns_number_gt 2574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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. Restraints on displacement parameters were used for carbon and nitrogen atoms of a N-alkyl chain (C9-C11) and disordered acetonitrile molecules (N2A, C14B-C15B, N2B, C14B-C14B). The anisotropic temperature factors of the atoms fitted into acceptable values by the restraints. Geometrical restraints for bond length were used for N-C and C-C bonds of the acetonitrile molecules (N2A-C14A, C14A-C15A, N2B-C14B, C14B-C15B). The atoms fitted into acceptable positions by the restraints. ; _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^)+(0.1822P)^2^+1.9114P] 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 3351 _refine_ls_number_parameters 192 _refine_ls_number_restraints 99 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.2769 _refine_ls_wR_factor_gt 0.2654 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.100 _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 C15A C 0.9902(6) 0.4096(9) 0.7500 0.090(4) Uani 0.327(6) 1 d PU A 1 C14A C 0.9016(7) 0.4033(11) 0.7500 0.097(4) Uani 0.327(6) 1 d PU A 1 N2A N 0.8318(12) 0.3955(17) 0.7500 0.163(9) Uani 0.327(6) 1 d PU A 1 N2B N 0.7438(8) 0.3540(8) 0.7500 0.061(4) Uani 0.173(6) 1 d PDU A 2 C14B C 0.8158(15) 0.342(3) 0.7500 0.134(12) Uani 0.173(6) 1 d PDU A 2 C15B C 0.911(2) 0.348(4) 0.7500 0.177(16) Uani 0.173(6) 1 d PDU A 2 C1 C 0.90159(15) 0.45012(16) 0.56903(11) 0.0303(5) Uani 1 1 d . . . C2 C 0.83590(15) 0.36162(16) 0.53150(12) 0.0299(5) Uani 1 1 d . . . C3 C 0.84269(14) 0.35329(16) 0.45969(12) 0.0308(5) Uani 1 1 d . . . H3 H 0.8881 0.4046 0.4334 0.037 Uiso 1 1 calc R . . C4 C 0.78278(16) 0.26957(16) 0.42645(12) 0.0324(5) Uani 1 1 d . . . C5 C 0.71695(16) 0.19323(16) 0.46445(13) 0.0340(5) Uani 1 1 d . . . H5 H 0.6778 0.1355 0.4419 0.041 Uiso 1 1 calc R . . C6 C 0.70964(15) 0.20310(16) 0.53587(12) 0.0327(5) Uani 1 1 d . . . C7 C 0.76865(16) 0.28660(16) 0.56967(12) 0.0331(6) Uani 1 1 d . . . H7 H 0.7630 0.2924 0.6186 0.040 Uiso 1 1 calc R . . C8 C 0.78710(16) 0.26441(16) 0.34925(12) 0.0354(6) Uani 1 1 d . . . C9 C 0.9266(2) 0.5993(2) 0.61832(17) 0.0539(8) Uani 1 1 d U . . H9A H 0.9773 0.5957 0.6429 0.065 Uiso 1 1 calc R . . H9B H 0.8839 0.5997 0.6543 0.065 Uiso 1 1 calc R . . C10 C 0.9678(2) 0.6884(2) 0.5792(2) 0.0694(10) Uani 1 1 d U . . H10A H 0.9175 0.6916 0.5536 0.083 Uiso 1 1 calc R . . H10B H 1.0120 0.6891 0.5441 0.083 Uiso 1 1 calc R . . C11 C 1.0187(3) 0.7748(3) 0.6255(4) 0.1019(18) Uani 1 1 d U . . H11A H 0.9729 0.7785 0.6565 0.122 Uiso 1 1 calc R . . H11B H 1.0637 0.7680 0.6555 0.122 Uiso 1 1 calc R . . C12 C 1.0700(5) 0.8640(3) 0.5850(5) 0.140(3) Uani 1 1 d U . . H12A H 1.0250 0.8726 0.5565 0.168 Uiso 1 1 calc R . . H12B H 1.1146 0.8600 0.5528 0.168 Uiso 1 1 calc R . . C13 C 1.1238(7) 0.9495(5) 0.6341(8) 0.238(6) Uani 1 1 d U . . H13A H 1.1036 0.9949 0.6250 0.357 Uiso 1 1 calc R . . H13B H 1.1908 0.9783 0.6253 0.357 Uiso 1 1 calc R . . H13C H 1.1107 0.9291 0.6830 0.357 Uiso 1 1 calc R . . N1 N 0.87481(13) 0.51471(15) 0.57494(10) 0.0364(5) Uani 1 1 d . . . O1 O 0.97385(11) 0.45947(12) 0.59468(9) 0.0391(5) Uani 1 1 d . . . O2 O 0.84318(13) 0.33827(14) 0.31713(9) 0.0499(6) Uani 1 1 d . . . H2 H 0.8401 0.3275 0.2740 0.075 Uiso 0.50 1 calc PR . . O3 O 0.73560(14) 0.18732(14) 0.31901(9) 0.0506(6) Uani 1 1 d . . . H3A H 0.7448 0.1938 0.2757 0.076 Uiso 0.50 1 calc PR . . 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 C15A 0.060(5) 0.214(12) 0.022(3) 0.000 0.000 0.088(6) C14A 0.059(5) 0.195(13) 0.045(4) 0.000 0.000 0.070(7) N2A 0.091(10) 0.27(2) 0.145(13) 0.000 0.000 0.099(14) N2B 0.061(7) 0.053(7) 0.066(7) 0.000 0.000 0.025(6) C14B 0.032(8) 0.31(4) 0.026(7) 0.000 0.000 0.057(14) C15B 0.16(2) 0.42(5) 0.027(8) 0.000 0.000 0.20(3) C1 0.0265(10) 0.0380(12) 0.0238(10) 0.0025(8) 0.0000(8) 0.0141(9) C2 0.0248(10) 0.0352(11) 0.0304(11) 0.0025(9) -0.0019(8) 0.0155(9) C3 0.0245(10) 0.0358(12) 0.0299(11) 0.0031(9) -0.0012(8) 0.0134(9) C4 0.0279(11) 0.0360(12) 0.0313(12) 0.0017(9) -0.0008(8) 0.0145(9) C5 0.0315(11) 0.0336(11) 0.0335(12) 0.0017(9) -0.0027(9) 0.0138(9) C6 0.0316(11) 0.0313(11) 0.0338(12) 0.0077(9) 0.0014(9) 0.0147(9) C7 0.0325(11) 0.0384(12) 0.0282(11) 0.0045(9) 0.0004(9) 0.0176(10) C8 0.0292(11) 0.0378(12) 0.0315(12) -0.0003(9) -0.0018(9) 0.0109(10) C9 0.0455(15) 0.0598(17) 0.0596(18) -0.0294(14) -0.0203(13) 0.0287(14) C10 0.0482(17) 0.0518(18) 0.108(3) -0.0170(18) -0.0112(18) 0.0248(15) C11 0.067(2) 0.069(2) 0.175(5) -0.047(3) -0.038(3) 0.038(2) C12 0.101(4) 0.056(3) 0.251(9) -0.030(3) -0.030(4) 0.030(3) C13 0.190(8) 0.076(4) 0.420(17) -0.096(7) -0.126(10) 0.046(5) N1 0.0330(10) 0.0433(12) 0.0331(10) -0.0094(8) -0.0106(8) 0.0193(9) O1 0.0291(9) 0.0440(10) 0.0404(10) 0.0006(7) -0.0064(7) 0.0154(7) O2 0.0442(10) 0.0515(11) 0.0267(9) 0.0008(7) -0.0010(7) 0.0034(8) O3 0.0557(12) 0.0430(11) 0.0361(10) -0.0065(8) -0.0057(8) 0.0118(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 C15A C14A 1.420(12) . ? C14A N2A 1.097(17) . ? N2B C14B 1.311(18) . ? C14B C15B 1.528(18) . ? C1 O1 1.231(3) . ? C1 N1 1.353(3) . ? C1 C2 1.502(3) . ? C2 C3 1.390(3) . ? C2 C7 1.391(3) . ? C3 C4 1.392(3) . ? C3 H3 0.9500 . ? C4 C5 1.393(3) . ? C4 C8 1.483(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9500 . ? C6 C7 1.392(3) . ? C6 N1 1.439(3) 3_665 ? C7 H7 0.9500 . ? C8 O2 1.266(3) . ? C8 O3 1.267(3) . ? C9 N1 1.479(3) . ? C9 C10 1.483(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.529(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.499(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.557(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 C6 1.439(3) 2_655 ? O2 H2 0.8400 . ? O3 H3A 0.8400 . ? 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 N2A C14A C15A 177.7(19) . . ? N2B C14B C15B 169(4) . . ? O1 C1 N1 123.4(2) . . ? O1 C1 C2 119.9(2) . . ? N1 C1 C2 116.64(18) . . ? C3 C2 C7 119.9(2) . . ? C3 C2 C1 120.92(19) . . ? C7 C2 C1 119.2(2) . . ? C2 C3 C4 119.8(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 C8 118.8(2) . . ? C5 C4 C8 120.4(2) . . ? C6 C5 C4 118.8(2) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C7 121.0(2) . . ? C5 C6 N1 118.9(2) . 3_665 ? C7 C6 N1 120.1(2) . 3_665 ? C2 C7 C6 119.7(2) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? O2 C8 O3 123.6(2) . . ? O2 C8 C4 117.4(2) . . ? O3 C8 C4 119.0(2) . . ? N1 C9 C10 114.9(3) . . ? N1 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? N1 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 113.9(4) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C10 113.6(6) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 111.8(8) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 N1 C6 121.09(19) . 2_655 ? C1 N1 C9 122.1(2) . . ? C6 N1 C9 116.7(2) 2_655 . ? C8 O2 H2 109.5 . . ? C8 O3 H3A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.899 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.086 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 14 0 ' ' 2 0.000 0.000 0.250 191 26 ' ' 3 0.000 0.000 0.500 14 0 ' ' 4 0.000 0.000 0.750 191 26 ' ' 5 0.333 0.666 0.750 24 1 ' ' 6 0.667 0.333 0.250 24 1 ' ' _platon_squeeze_details ; ; #===END data_a1001161mas _database_code_depnum_ccdc_archive 'CCDC 859944' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H52 N6 O7.50' _chemical_formula_weight 736.88 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 15.2474(12) _cell_length_b 29.608(2) _cell_length_c 9.3379(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.0930(10) _cell_angle_gamma 90.00 _cell_volume 4106.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 250 _cell_measurement_reflns_used 5441 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 24.85 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9675 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 250 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 20265 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.23 _reflns_number_total 8364 _reflns_number_gt 5650 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.1159P)^2^+0.6063P] 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 8364 _refine_ls_number_parameters 492 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.2043 _refine_ls_wR_factor_gt 0.1817 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.069 _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 0.25333(14) 0.79242(7) 0.3558(2) 0.0395(5) Uani 1 1 d . . . C2 C 0.33118(14) 0.81435(7) 0.3084(2) 0.0370(5) Uani 1 1 d . . . C3 C 0.39344(14) 0.83907(7) 0.4098(2) 0.0382(5) Uani 1 1 d . . . H3 H 0.3852 0.8429 0.5059 0.046 Uiso 1 1 calc R . . C4 C 0.46784(14) 0.85825(7) 0.3708(2) 0.0389(5) Uani 1 1 d . . . C5 C 0.48007(15) 0.85198(7) 0.2291(2) 0.0400(5) Uani 1 1 d . . . H5 H 0.5314 0.8638 0.2024 0.048 Uiso 1 1 calc R . . C6 C 0.41649(15) 0.82833(7) 0.1275(2) 0.0389(5) Uani 1 1 d . . . C7 C 0.34290(14) 0.80887(7) 0.1666(2) 0.0389(5) Uani 1 1 d . . . H7 H 0.3011 0.7920 0.0975 0.047 Uiso 1 1 calc R . . C8 C 0.38911(15) 0.85499(8) -0.1244(2) 0.0440(5) Uani 1 1 d . . . C9 C 0.35198(14) 0.89713(8) -0.0720(2) 0.0410(5) Uani 1 1 d . . . C10 C 0.40978(15) 0.92988(8) 0.0054(2) 0.0414(5) Uani 1 1 d . . . H10 H 0.4723 0.9249 0.0269 0.050 Uiso 1 1 calc R . . C11 C 0.37652(14) 0.96940(8) 0.0505(2) 0.0410(5) Uani 1 1 d . . . C12 C 0.28433(15) 0.97736(8) 0.0157(2) 0.0447(5) Uani 1 1 d . . . H12 H 0.2613 1.0048 0.0420 0.054 Uiso 1 1 calc R . . C13 C 0.22663(14) 0.94447(9) -0.0583(2) 0.0452(5) Uani 1 1 d . . . C14 C 0.25987(15) 0.90512(8) -0.1035(2) 0.0461(6) Uani 1 1 d . . . H14 H 0.2200 0.8835 -0.1560 0.055 Uiso 1 1 calc R . . C15 C 0.08054(15) 0.93672(8) 0.0028(2) 0.0453(5) Uani 1 1 d . . . C16 C 0.13134(14) 0.92349(8) 0.1548(2) 0.0400(5) Uani 1 1 d . . . C17 C 0.17389(13) 0.95667(8) 0.2515(2) 0.0410(5) Uani 1 1 d . . . H17 H 0.1696 0.9871 0.2222 0.049 Uiso 1 1 calc R . . C18 C 0.22261(13) 0.94512(7) 0.3909(2) 0.0389(5) Uani 1 1 d . . . C19 C 0.22606(14) 0.90055(7) 0.4360(2) 0.0405(5) Uani 1 1 d . . . H19 H 0.2571 0.8927 0.5316 0.049 Uiso 1 1 calc R . . C20 C 0.18368(14) 0.86737(7) 0.3401(2) 0.0404(5) Uani 1 1 d . . . C21 C 0.13578(14) 0.87892(8) 0.2003(2) 0.0425(5) Uani 1 1 d . . . H21 H 0.1062 0.8564 0.1362 0.051 Uiso 1 1 calc R . . C22 C 0.53376(16) 0.88860(8) 0.4718(2) 0.0451(5) Uani 1 1 d . . . C23 C 0.43628(15) 1.00435(8) 0.1399(2) 0.0452(5) Uani 1 1 d . . . C24 C 0.28016(15) 0.97855(8) 0.4926(3) 0.0465(5) Uani 1 1 d . . . C25 C 0.11522(16) 0.80234(8) 0.4439(3) 0.0490(6) Uani 1 1 d . . . H25A H 0.1196 0.7693 0.4480 0.059 Uiso 1 1 calc R . . H25B H 0.0577 0.8102 0.3777 0.059 Uiso 1 1 calc R . . C26 C 0.11638(17) 0.82024(9) 0.5959(3) 0.0500(6) Uani 1 1 d . . . H26A H 0.1113 0.8532 0.5918 0.060 Uiso 1 1 calc R . . H26B H 0.1740 0.8126 0.6620 0.060 Uiso 1 1 calc R . . C27 C 0.04004(17) 0.80096(9) 0.6575(3) 0.0548(6) Uani 1 1 d . . . H27A H -0.0172 0.8068 0.5875 0.066 Uiso 1 1 calc R . . H27B H 0.0476 0.7682 0.6673 0.066 Uiso 1 1 calc R . . C28 C 0.0357(2) 0.82068(11) 0.8056(3) 0.0690(8) Uani 1 1 d . . . H28A H 0.0925 0.8144 0.8761 0.083 Uiso 1 1 calc R . . H28B H 0.0293 0.8536 0.7961 0.083 Uiso 1 1 calc R . . C29 C -0.0413(2) 0.80219(13) 0.8659(4) 0.0871(10) Uani 1 1 d . . . H29A H -0.0982 0.8110 0.8019 0.131 Uiso 1 1 calc R . . H29B H -0.0377 0.8142 0.9637 0.131 Uiso 1 1 calc R . . H29C H -0.0374 0.7695 0.8708 0.131 Uiso 1 1 calc R . . C30 C 0.46881(18) 0.78366(9) -0.0638(3) 0.0576(6) Uani 1 1 d . . . H30A H 0.4416 0.7760 -0.1663 0.069 Uiso 1 1 calc R . . H30B H 0.4583 0.7584 -0.0021 0.069 Uiso 1 1 calc R . . C31 C 0.5697(2) 0.79040(14) -0.0458(5) 0.0943(11) Uani 1 1 d . . . H31A H 0.5799 0.8139 -0.1141 0.113 Uiso 1 1 calc R . . H31B H 0.5957 0.8009 0.0543 0.113 Uiso 1 1 calc R . . C32 C 0.6164(3) 0.74810(17) -0.0742(6) 0.1228(16) Uani 1 1 d . . . H32A H 0.5912 0.7386 -0.1757 0.147 Uiso 1 1 calc R . . H32B H 0.6027 0.7244 -0.0094 0.147 Uiso 1 1 calc R . . C33 C 0.7163(4) 0.7513(3) -0.0523(10) 0.193(3) Uani 1 1 d . . . H33A H 0.7311 0.7718 -0.1257 0.232 Uiso 1 1 calc R . . H33B H 0.7421 0.7637 0.0454 0.232 Uiso 1 1 calc R . . C34 C 0.7557(5) 0.7072(3) -0.0659(11) 0.233(4) Uani 1 1 d . . . H34A H 0.7474 0.6879 0.0139 0.349 Uiso 1 1 calc R . . H34B H 0.8195 0.7106 -0.0615 0.349 Uiso 1 1 calc R . . H34C H 0.7265 0.6937 -0.1591 0.349 Uiso 1 1 calc R . . C35 C 0.0879(2) 0.96925(14) -0.2366(3) 0.0846(10) Uani 1 1 d U . . H35A H 0.0222 0.9672 -0.2528 0.102 Uiso 1 1 calc R . . H35B H 0.1067 0.9512 -0.3124 0.102 Uiso 1 1 calc R . . C36 C 0.1173(3) 1.02159(17) -0.2495(4) 0.1114(13) Uani 1 1 d U . . H36A H 0.1044 1.0384 -0.1661 0.134 Uiso 1 1 calc R . . H36B H 0.1825 1.0227 -0.2408 0.134 Uiso 1 1 calc R . . C37 C 0.0740(3) 1.0441(2) -0.3823(6) 0.1347(16) Uani 1 1 d U . . H37A H 0.0093 1.0456 -0.3865 0.162 Uiso 1 1 calc R . . H37B H 0.0822 1.0259 -0.4659 0.162 Uiso 1 1 calc R . . C38 C 0.1081(5) 1.0917(2) -0.3990(8) 0.164(2) Uani 1 1 d U . . H38A H 0.1716 1.0899 -0.4038 0.197 Uiso 1 1 calc R . . H38B H 0.0745 1.1041 -0.4927 0.197 Uiso 1 1 calc R . . C39 C 0.1008(6) 1.1210(3) -0.2887(10) 0.220(4) Uani 1 1 d U . . H39A H 0.0399 1.1202 -0.2740 0.330 Uiso 1 1 calc R . . H39B H 0.1148 1.1514 -0.3155 0.330 Uiso 1 1 calc R . . H39C H 0.1427 1.1122 -0.1985 0.330 Uiso 1 1 calc R . . C40 C 0.7789(3) 0.89308(15) 0.8321(7) 0.144(2) Uani 1 1 d . . . H40A H 0.7217 0.8991 0.8575 0.217 Uiso 1 1 calc R . . H40B H 0.8162 0.8748 0.9084 0.217 Uiso 1 1 calc R . . H40C H 0.7683 0.8770 0.7393 0.217 Uiso 1 1 calc R . . N1 N 0.18919(13) 0.82042(6) 0.3836(2) 0.0441(4) Uani 1 1 d . . . N2 N 0.42598(13) 0.82446(6) -0.02240(18) 0.0431(4) Uani 1 1 d . . . N3 N 0.13003(12) 0.95122(8) -0.0900(2) 0.0514(5) Uani 1 1 d . . . N4 N 0.52328(15) 0.89444(8) 0.6063(2) 0.0628(6) Uani 1 1 d . . . H4A H 0.5589 0.9126 0.6659 0.075 Uiso 1 1 calc R . . H4B H 0.4808 0.8801 0.6358 0.075 Uiso 1 1 calc R . . N5 N 0.51571(13) 0.99033(7) 0.2167(2) 0.0575(6) Uani 1 1 d . . . H5A H 0.5529 1.0094 0.2692 0.069 Uiso 1 1 calc R . . H5B H 0.5306 0.9620 0.2145 0.069 Uiso 1 1 calc R . . N6 N 0.28035(15) 1.02099(7) 0.4474(2) 0.0617(6) Uani 1 1 d . . . H6A H 0.3140 1.0410 0.5023 0.074 Uiso 1 1 calc R . . H6B H 0.2468 1.0289 0.3628 0.074 Uiso 1 1 calc R . . O1 O 0.25079(12) 0.75150(5) 0.37146(19) 0.0553(4) Uani 1 1 d . . . O2 O 0.38725(14) 0.84949(7) -0.25577(16) 0.0659(5) Uani 1 1 d . . . O3 O -0.00166(11) 0.93460(8) -0.0311(2) 0.0681(5) Uani 1 1 d . . . O4 O 0.59270(13) 0.90792(7) 0.4239(2) 0.0718(6) Uani 1 1 d . . . O5 O 0.41208(12) 1.04390(6) 0.1393(2) 0.0637(5) Uani 1 1 d . . . O6 O 0.32602(15) 0.96589(7) 0.6103(2) 0.0790(7) Uani 1 1 d . . . O7 O 0.82168(16) 0.93303(8) 0.8195(3) 0.1078(10) Uani 1 1 d . . . H7A H 0.8766 0.9300 0.8533 0.162 Uiso 1 1 calc R . . O8 O 0.6518(5) 0.9059(3) 0.1158(10) 0.162(3) Uani 0.50 1 d P . . 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 0.0489(12) 0.0423(12) 0.0256(10) -0.0001(9) 0.0049(9) -0.0079(10) C2 0.0473(12) 0.0347(10) 0.0289(10) 0.0000(8) 0.0082(9) -0.0037(9) C3 0.0483(12) 0.0434(12) 0.0228(9) -0.0017(8) 0.0078(9) -0.0034(9) C4 0.0463(12) 0.0399(11) 0.0294(10) -0.0032(9) 0.0067(9) -0.0045(9) C5 0.0460(12) 0.0422(12) 0.0333(11) -0.0022(9) 0.0123(9) -0.0073(9) C6 0.0525(13) 0.0397(11) 0.0256(10) -0.0039(8) 0.0110(9) -0.0020(9) C7 0.0480(12) 0.0400(11) 0.0273(10) -0.0053(8) 0.0055(9) -0.0065(9) C8 0.0501(13) 0.0571(14) 0.0268(10) -0.0053(10) 0.0124(9) -0.0159(11) C9 0.0467(12) 0.0541(13) 0.0228(9) 0.0019(9) 0.0089(9) -0.0096(10) C10 0.0402(11) 0.0554(13) 0.0276(10) 0.0025(9) 0.0054(8) -0.0067(10) C11 0.0412(11) 0.0511(13) 0.0296(10) 0.0023(9) 0.0058(9) -0.0079(10) C12 0.0430(12) 0.0521(13) 0.0366(11) 0.0040(10) 0.0041(9) -0.0050(10) C13 0.0390(11) 0.0616(15) 0.0319(11) 0.0054(10) 0.0013(9) -0.0064(10) C14 0.0475(13) 0.0613(15) 0.0264(10) 0.0032(10) 0.0015(9) -0.0160(11) C15 0.0377(12) 0.0519(13) 0.0423(12) -0.0041(10) 0.0008(9) -0.0054(10) C16 0.0336(10) 0.0482(13) 0.0374(11) -0.0031(9) 0.0062(8) -0.0062(9) C17 0.0365(11) 0.0411(12) 0.0438(12) -0.0003(9) 0.0060(9) -0.0044(9) C18 0.0361(11) 0.0454(12) 0.0348(11) -0.0031(9) 0.0071(8) -0.0075(9) C19 0.0404(11) 0.0456(12) 0.0356(11) -0.0003(9) 0.0088(9) -0.0055(9) C20 0.0416(11) 0.0413(11) 0.0405(11) -0.0014(9) 0.0139(9) -0.0069(9) C21 0.0428(12) 0.0459(13) 0.0391(11) -0.0087(10) 0.0103(9) -0.0117(10) C22 0.0490(13) 0.0480(13) 0.0367(11) -0.0053(10) 0.0063(10) -0.0098(10) C23 0.0444(12) 0.0522(14) 0.0372(11) -0.0046(10) 0.0058(9) -0.0073(11) C24 0.0456(12) 0.0493(13) 0.0417(12) -0.0018(10) 0.0039(10) -0.0124(10) C25 0.0529(13) 0.0460(13) 0.0525(14) -0.0026(11) 0.0212(11) -0.0131(10) C26 0.0561(14) 0.0528(14) 0.0434(13) 0.0017(10) 0.0163(11) -0.0049(11) C27 0.0587(15) 0.0577(15) 0.0521(14) 0.0041(12) 0.0214(12) -0.0052(12) C28 0.081(2) 0.0725(19) 0.0626(17) -0.0016(14) 0.0340(15) -0.0002(15) C29 0.088(2) 0.105(3) 0.083(2) 0.014(2) 0.0500(19) 0.014(2) C30 0.0740(17) 0.0571(15) 0.0459(13) -0.0148(12) 0.0226(12) -0.0007(13) C31 0.082(2) 0.099(3) 0.104(3) -0.031(2) 0.028(2) 0.006(2) C32 0.094(3) 0.127(4) 0.150(4) -0.046(3) 0.032(3) 0.014(3) C33 0.111(4) 0.199(7) 0.278(9) -0.062(6) 0.061(5) 0.036(4) C34 0.154(6) 0.241(9) 0.290(10) -0.042(8) 0.025(6) 0.088(6) C35 0.0525(16) 0.147(3) 0.0467(15) 0.0321(18) -0.0042(12) -0.0023(18) C36 0.086(2) 0.159(3) 0.084(2) 0.048(3) 0.0099(19) -0.003(2) C37 0.110(3) 0.171(4) 0.118(3) 0.062(3) 0.015(3) 0.009(3) C38 0.196(6) 0.127(4) 0.179(6) 0.047(4) 0.060(5) 0.026(4) C39 0.264(9) 0.171(6) 0.250(9) 0.030(5) 0.113(8) 0.044(6) C40 0.097(3) 0.088(3) 0.221(6) 0.010(3) -0.020(3) 0.005(3) N1 0.0523(11) 0.0371(10) 0.0464(10) -0.0005(8) 0.0185(9) -0.0094(8) N2 0.0559(11) 0.0489(11) 0.0273(9) -0.0087(8) 0.0155(8) -0.0068(9) N3 0.0386(10) 0.0734(14) 0.0360(10) 0.0086(9) -0.0042(8) -0.0051(9) N4 0.0690(14) 0.0822(16) 0.0367(11) -0.0230(10) 0.0112(10) -0.0293(12) N5 0.0506(12) 0.0567(13) 0.0549(12) -0.0067(10) -0.0096(9) -0.0087(10) N6 0.0691(14) 0.0467(12) 0.0577(13) -0.0030(10) -0.0101(10) -0.0174(10) O1 0.0621(11) 0.0417(10) 0.0646(11) 0.0071(8) 0.0199(9) -0.0057(8) O2 0.0934(14) 0.0802(13) 0.0267(8) -0.0075(8) 0.0193(8) -0.0074(10) O3 0.0363(9) 0.1040(16) 0.0579(11) 0.0056(10) -0.0019(8) -0.0068(9) O4 0.0756(12) 0.0871(14) 0.0555(11) -0.0227(10) 0.0205(10) -0.0431(11) O5 0.0556(10) 0.0599(12) 0.0686(12) -0.0186(9) -0.0006(9) -0.0026(9) O6 0.0959(15) 0.0709(13) 0.0500(11) 0.0115(9) -0.0261(10) -0.0326(11) O7 0.0707(14) 0.0746(15) 0.146(2) 0.0182(15) -0.0425(15) -0.0007(12) O8 0.147(6) 0.164(7) 0.179(7) 0.050(6) 0.042(5) -0.025(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 O1 1.222(3) . ? C1 N1 1.351(3) . ? C1 C2 1.505(3) . ? C2 C7 1.385(3) . ? C2 C3 1.388(3) . ? C3 C4 1.389(3) . ? C3 H3 0.9400 . ? C4 C5 1.390(3) . ? C4 C22 1.509(3) . ? C5 C6 1.383(3) . ? C5 H5 0.9400 . ? C6 C7 1.382(3) . ? C6 N2 1.444(2) . ? C7 H7 0.9400 . ? C8 O2 1.231(2) . ? C8 N2 1.341(3) . ? C8 C9 1.498(3) . ? C9 C14 1.388(3) . ? C9 C10 1.396(3) . ? C10 C11 1.379(3) . ? C10 H10 0.9400 . ? C11 C12 1.389(3) . ? C11 C23 1.501(3) . ? C12 C13 1.387(3) . ? C12 H12 0.9400 . ? C13 C14 1.375(4) . ? C13 N3 1.449(3) . ? C14 H14 0.9400 . ? C15 O3 1.223(3) . ? C15 N3 1.342(3) . ? C15 C16 1.507(3) . ? C16 C21 1.383(3) . ? C16 C17 1.392(3) . ? C17 C18 1.388(3) . ? C17 H17 0.9400 . ? C18 C19 1.383(3) . ? C18 C24 1.508(3) . ? C19 C20 1.386(3) . ? C19 H19 0.9400 . ? C20 C21 1.387(3) . ? C20 N1 1.445(3) . ? C21 H21 0.9400 . ? C22 O4 1.232(3) . ? C22 N4 1.313(3) . ? C23 O5 1.227(3) . ? C23 N5 1.327(3) . ? C24 O6 1.220(3) . ? C24 N6 1.326(3) . ? C25 N1 1.471(3) . ? C25 C26 1.511(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C26 C27 1.521(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C27 C28 1.517(4) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C28 C29 1.515(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C30 N2 1.466(3) . ? C30 C31 1.522(4) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C31 C32 1.494(5) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C32 C33 1.494(7) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C33 C34 1.454(9) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 H34C 0.9700 . ? C35 N3 1.474(3) . ? C35 C36 1.625(6) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C36 C37 1.430(5) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C37 C38 1.522(8) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C38 C39 1.371(9) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C39 H39C 0.9700 . ? C40 O7 1.369(5) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C40 H40C 0.9700 . ? N4 H4A 0.8700 . ? N4 H4B 0.8700 . ? N5 H5A 0.8700 . ? N5 H5B 0.8700 . ? N6 H6A 0.8700 . ? N6 H6B 0.8700 . ? O7 H7A 0.8300 . ? 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 O1 C1 N1 122.8(2) . . ? O1 C1 C2 120.8(2) . . ? N1 C1 C2 116.44(18) . . ? C7 C2 C3 119.86(19) . . ? C7 C2 C1 120.78(18) . . ? C3 C2 C1 119.32(17) . . ? C2 C3 C4 120.62(18) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.26(18) . . ? C3 C4 C22 123.21(18) . . ? C5 C4 C22 117.39(19) . . ? C6 C5 C4 119.74(19) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 120.99(18) . . ? C7 C6 N2 119.24(18) . . ? C5 C6 N2 119.76(19) . . ? C6 C7 C2 119.46(19) . . ? C6 C7 H7 120.3 . . ? C2 C7 H7 120.3 . . ? O2 C8 N2 122.0(2) . . ? O2 C8 C9 120.7(2) . . ? N2 C8 C9 117.24(17) . . ? C14 C9 C10 118.8(2) . . ? C14 C9 C8 120.8(2) . . ? C10 C9 C8 120.4(2) . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.7(2) . . ? C10 C11 C23 122.4(2) . . ? C12 C11 C23 117.9(2) . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C14 C13 C12 120.8(2) . . ? C14 C13 N3 118.9(2) . . ? C12 C13 N3 120.4(2) . . ? C13 C14 C9 120.3(2) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? O3 C15 N3 122.9(2) . . ? O3 C15 C16 120.6(2) . . ? N3 C15 C16 116.56(19) . . ? C21 C16 C17 119.4(2) . . ? C21 C16 C15 121.09(19) . . ? C17 C16 C15 119.5(2) . . ? C18 C17 C16 120.4(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 119.74(19) . . ? C19 C18 C24 117.29(19) . . ? C17 C18 C24 122.7(2) . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C21 120.1(2) . . ? C19 C20 N1 120.76(19) . . ? C21 C20 N1 119.10(19) . . ? C16 C21 C20 120.2(2) . . ? C16 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? O4 C22 N4 122.9(2) . . ? O4 C22 C4 119.17(19) . . ? N4 C22 C4 117.9(2) . . ? O5 C23 N5 122.6(2) . . ? O5 C23 C11 120.7(2) . . ? N5 C23 C11 116.7(2) . . ? O6 C24 N6 122.4(2) . . ? O6 C24 C18 119.9(2) . . ? N6 C24 C18 117.7(2) . . ? N1 C25 C26 112.64(19) . . ? N1 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? N1 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C25 C26 C27 112.1(2) . . ? C25 C26 H26A 109.2 . . ? C27 C26 H26A 109.2 . . ? C25 C26 H26B 109.2 . . ? C27 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C28 C27 C26 113.3(2) . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? C29 C28 C27 113.4(3) . . ? C29 C28 H28A 108.9 . . ? C27 C28 H28A 108.9 . . ? C29 C28 H28B 108.9 . . ? C27 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N2 C30 C31 111.2(2) . . ? N2 C30 H30A 109.4 . . ? C31 C30 H30A 109.4 . . ? N2 C30 H30B 109.4 . . ? C31 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C32 C31 C30 112.4(3) . . ? C32 C31 H31A 109.1 . . ? C30 C31 H31A 109.1 . . ? C32 C31 H31B 109.1 . . ? C30 C31 H31B 109.1 . . ? H31A C31 H31B 107.9 . . ? C31 C32 C33 115.8(4) . . ? C31 C32 H32A 108.3 . . ? C33 C32 H32A 108.3 . . ? C31 C32 H32B 108.3 . . ? C33 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? C34 C33 C32 111.1(6) . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N3 C35 C36 110.1(3) . . ? N3 C35 H35A 109.6 . . ? C36 C35 H35A 109.6 . . ? N3 C35 H35B 109.6 . . ? C36 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? C37 C36 C35 115.3(4) . . ? C37 C36 H36A 108.4 . . ? C35 C36 H36A 108.4 . . ? C37 C36 H36B 108.4 . . ? C35 C36 H36B 108.4 . . ? H36A C36 H36B 107.5 . . ? C36 C37 C38 114.8(5) . . ? C36 C37 H37A 108.6 . . ? C38 C37 H37A 108.6 . . ? C36 C37 H37B 108.6 . . ? C38 C37 H37B 108.6 . . ? H37A C37 H37B 107.5 . . ? C39 C38 C37 114.9(6) . . ? C39 C38 H38A 108.5 . . ? C37 C38 H38A 108.5 . . ? C39 C38 H38B 108.5 . . ? C37 C38 H38B 108.5 . . ? H38A C38 H38B 107.5 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? O7 C40 H40A 109.5 . . ? O7 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O7 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C1 N1 C20 122.31(17) . . ? C1 N1 C25 120.10(19) . . ? C20 N1 C25 117.18(18) . . ? C8 N2 C6 121.16(18) . . ? C8 N2 C30 120.54(18) . . ? C6 N2 C30 117.99(19) . . ? C15 N3 C13 121.23(18) . . ? C15 N3 C35 121.7(2) . . ? C13 N3 C35 116.7(2) . . ? C22 N4 H4A 120.0 . . ? C22 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C23 N5 H5A 120.0 . . ? C23 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C24 N6 H6A 120.0 . . ? C24 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? C40 O7 H7A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.597 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.049 # Attachment 'a1009061mas_p43.cif' data_a1009061mas_p43 _database_code_depnum_ccdc_archive 'CCDC 859945' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H36 N6 O6, 2(C2 H3 N), 2(H2 O)' _chemical_formula_sum 'C37 H46 N8 O8' _chemical_formula_weight 730.82 _chemical_absolute_configuration unk 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 Tetragonal _symmetry_space_group_name_H-M 'P4(3)2(1)2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 15.344(15) _cell_length_b 15.344(15) _cell_length_c 38.99(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9180(16) _cell_formula_units_Z 8 _cell_measurement_temperature 253 _cell_measurement_reflns_used 7012 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 19.15 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.058 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3104 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9559 _exptl_absorpt_correction_T_max 0.9703 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 253 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 45859 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 27.31 _reflns_number_total 9671 _reflns_number_gt 5030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.1855P)^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 SHELXL _refine_ls_extinction_coef 0.0026(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 9671 _refine_ls_number_parameters 509 _refine_ls_number_restraints 102 _refine_ls_R_factor_all 0.1355 _refine_ls_R_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.2729 _refine_ls_wR_factor_gt 0.2408 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.946 _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 C28A C 0.3998(9) 0.4835(12) 0.1946(6) 0.193(6) Uani 0.747(14) 1 d PDU A 1 H28A H 0.4127 0.4381 0.2112 0.232 Uiso 0.747(14) 1 calc PR A 1 H28B H 0.3939 0.5383 0.2068 0.232 Uiso 0.747(14) 1 calc PR A 1 C29A C 0.3182(8) 0.4631(10) 0.1762(5) 0.213(6) Uani 0.747(14) 1 d PDU A 1 H29A H 0.3258 0.4129 0.1614 0.255 Uiso 0.747(14) 1 calc PR A 1 H29B H 0.2993 0.5122 0.1625 0.255 Uiso 0.747(14) 1 calc PR A 1 C30A C 0.2532(10) 0.4438(13) 0.2043(6) 0.267(9) Uani 0.747(14) 1 d PDU A 1 H30A H 0.2712 0.3927 0.2166 0.401 Uiso 0.747(14) 1 calc PR A 1 H30B H 0.1968 0.4341 0.1943 0.401 Uiso 0.747(14) 1 calc PR A 1 H30C H 0.2504 0.4924 0.2198 0.401 Uiso 0.747(14) 1 calc PR A 1 C28B C 0.399(3) 0.477(2) 0.1888(5) 0.121(10) Uani 0.253(14) 1 d PDU A 2 H28C H 0.3816 0.4167 0.1864 0.145 Uiso 0.253(14) 1 calc PR A 2 H28D H 0.3522 0.5120 0.1789 0.145 Uiso 0.253(14) 1 calc PR A 2 C29B C 0.4008(17) 0.4966(16) 0.2258(4) 0.133(9) Uani 0.253(14) 1 d PDU A 2 H29C H 0.4095 0.5581 0.2305 0.159 Uiso 0.253(14) 1 calc PR A 2 H29D H 0.4439 0.4622 0.2379 0.159 Uiso 0.253(14) 1 calc PR A 2 C30B C 0.3064(18) 0.467(2) 0.2334(6) 0.159(11) Uani 0.253(14) 1 d PDU A 2 H30D H 0.2702 0.5166 0.2375 0.239 Uiso 0.253(14) 1 calc PR A 2 H30E H 0.3061 0.4298 0.2533 0.239 Uiso 0.253(14) 1 calc PR A 2 H30F H 0.2842 0.4346 0.2141 0.239 Uiso 0.253(14) 1 calc PR A 2 C1 C 0.8577(3) 0.5829(3) 0.15145(10) 0.0673(10) Uani 1 1 d . . . C2 C 0.7532(3) 0.4773(3) 0.13031(10) 0.0691(11) Uani 1 1 d . . . C3 C 0.7457(3) 0.4619(3) 0.09564(10) 0.0694(10) Uani 1 1 d . . . H3 H 0.7938 0.4700 0.0815 0.083 Uiso 1 1 calc R . . C4 C 0.6691(3) 0.4350(3) 0.08190(11) 0.0719(11) Uani 1 1 d . . . C5 C 0.5964(3) 0.4231(3) 0.10261(10) 0.0714(11) Uani 1 1 d . . . H5 H 0.5437 0.4053 0.0932 0.086 Uiso 1 1 calc R . . C6 C 0.6036(3) 0.4382(3) 0.13782(11) 0.0714(11) Uani 1 1 d . . . C7 C 0.6815(3) 0.4661(3) 0.15111(11) 0.0767(12) Uani 1 1 d . . . H7 H 0.6860 0.4777 0.1745 0.092 Uiso 1 1 calc R . . C8 C 0.6606(3) 0.4241(4) 0.04400(11) 0.0840(13) Uani 1 1 d . . . C9 C 0.5280(3) 0.4220(3) 0.16104(11) 0.0770(12) Uani 1 1 d . A . C10 C 0.4854(3) 0.5704(3) 0.15035(11) 0.0690(10) Uani 1 1 d . A . C11 C 0.4624(3) 0.5782(3) 0.11632(11) 0.0719(11) Uani 1 1 d . . . H11 H 0.4369 0.5311 0.1052 0.086 Uiso 1 1 calc R . . C12 C 0.4765(3) 0.6549(3) 0.09827(10) 0.0632(9) Uani 1 1 d . . . C13 C 0.5125(2) 0.7245(3) 0.11521(10) 0.0607(9) Uani 1 1 d . . . H13 H 0.5226 0.7763 0.1035 0.073 Uiso 1 1 calc R . . C14 C 0.5340(2) 0.7180(3) 0.14984(10) 0.0632(9) Uani 1 1 d . . . C15 C 0.5196(3) 0.6423(3) 0.16720(11) 0.0723(11) Uani 1 1 d . . . H15 H 0.5327 0.6388 0.1904 0.087 Uiso 1 1 calc R . . C16 C 0.4556(3) 0.6563(3) 0.06071(11) 0.0699(10) Uani 1 1 d . . . C17 C 0.5672(2) 0.7965(3) 0.16855(10) 0.0655(10) Uani 1 1 d . . . C18 C 0.7062(2) 0.7751(2) 0.14134(10) 0.0616(9) Uani 1 1 d . . . C19 C 0.7247(2) 0.8008(2) 0.10845(10) 0.0591(9) Uani 1 1 d . . . H19 H 0.6983 0.8504 0.0995 0.071 Uiso 1 1 calc R . . C20 C 0.7823(2) 0.7536(2) 0.08852(9) 0.0588(9) Uani 1 1 d . . . C21 C 0.8232(2) 0.6800(3) 0.10249(9) 0.0592(9) Uani 1 1 d . . . H21 H 0.8627 0.6482 0.0895 0.071 Uiso 1 1 calc R . . C22 C 0.8044(2) 0.6552(2) 0.13565(9) 0.0596(9) Uani 1 1 d . . . C23 C 0.7468(3) 0.7048(3) 0.15533(10) 0.0708(11) Uani 1 1 d . . . H23 H 0.7361 0.6897 0.1780 0.085 Uiso 1 1 calc R . . C24 C 0.7963(2) 0.7813(3) 0.05215(9) 0.0656(10) Uani 1 1 d . . . C25 C 0.8859(4) 0.4298(4) 0.16064(19) 0.119(2) Uani 1 1 d U . . H25A H 0.9280 0.4546 0.1764 0.143 Uiso 1 1 calc R . . H25B H 0.8479 0.3915 0.1736 0.143 Uiso 1 1 calc R . . C26 C 0.9315(7) 0.3795(6) 0.1346(3) 0.178(4) Uani 1 1 d U . . H26A H 0.9729 0.4153 0.1221 0.213 Uiso 1 1 calc R . . H26B H 0.8910 0.3535 0.1184 0.213 Uiso 1 1 calc R . . C27 C 0.9820(13) 0.3037(9) 0.1579(5) 0.330(10) Uani 1 1 d U . . H27A H 0.9554 0.3003 0.1801 0.495 Uiso 1 1 calc R . . H27B H 1.0424 0.3189 0.1603 0.495 Uiso 1 1 calc R . . H27C H 0.9774 0.2483 0.1466 0.495 Uiso 1 1 calc R . . C31 C 0.6816(5) 0.9053(4) 0.1793(2) 0.141(2) Uani 1 1 d U . . H31A H 0.6378 0.9509 0.1797 0.169 Uiso 1 1 calc R . . H31B H 0.7321 0.9268 0.1669 0.169 Uiso 1 1 calc R . . C32 C 0.7110(9) 0.8764(8) 0.2214(3) 0.277(7) Uani 1 1 d U . . H32A H 0.6631 0.8479 0.2332 0.332 Uiso 1 1 calc R . . H32B H 0.7612 0.8380 0.2215 0.332 Uiso 1 1 calc R . . C33 C 0.7330(14) 0.9660(11) 0.2384(4) 0.335(10) Uani 1 1 d U . . H33A H 0.7890 0.9855 0.2305 0.503 Uiso 1 1 calc R . . H33B H 0.7341 0.9595 0.2629 0.503 Uiso 1 1 calc R . . H33C H 0.6894 1.0080 0.2321 0.503 Uiso 1 1 calc R . . N1 N 0.8337(2) 0.5007(2) 0.14519(9) 0.0745(9) Uani 1 1 d . . . N2 N 0.4748(3) 0.4901(3) 0.16770(9) 0.0842(10) Uani 1 1 d . . . N3 N 0.6456(2) 0.8248(2) 0.16171(9) 0.0732(9) Uani 1 1 d . . . N4 N 0.5853(3) 0.4419(3) 0.02934(9) 0.0872(11) Uani 1 1 d . . . H4A H 0.5796 0.4366 0.0075 0.105 Uiso 1 1 calc R . . H4B H 0.5419 0.4588 0.0416 0.105 Uiso 1 1 calc R . . N5 N 0.4383(2) 0.7306(2) 0.04689(9) 0.0771(10) Uani 1 1 d . . . H5A H 0.4258 0.7336 0.0254 0.093 Uiso 1 1 calc R . . H5B H 0.4391 0.7772 0.0591 0.093 Uiso 1 1 calc R . . N6 N 0.8636(2) 0.7512(3) 0.03509(9) 0.0812(10) Uani 1 1 d . . . H6A H 0.8722 0.7673 0.0142 0.097 Uiso 1 1 calc R . . H6B H 0.8991 0.7155 0.0448 0.097 Uiso 1 1 calc R . . N7 N 0.4199(8) 0.2936(9) 0.27074(19) 0.238(5) Uani 1 1 d DU . . C34 C 0.4110(8) 0.2428(9) 0.2470(3) 0.199(4) Uani 1 1 d DU . . C35 C 0.3985(11) 0.2099(8) 0.2132(3) 0.267(8) Uani 1 1 d DU . . H35A H 0.3657 0.2512 0.1999 0.401 Uiso 1 1 calc R . . H35B H 0.3674 0.1557 0.2142 0.401 Uiso 1 1 calc R . . H35C H 0.4542 0.2006 0.2025 0.401 Uiso 1 1 calc R . . N8 N 0.8540(15) 0.1244(14) 0.1612(7) 0.398(13) Uani 1 1 d DU . . C36 C 0.7816(15) 0.1619(11) 0.1539(6) 0.298(9) Uani 1 1 d DU . . C37 C 0.7002(12) 0.2091(15) 0.1480(7) 0.382(14) Uani 1 1 d DU . . H37A H 0.6718 0.2196 0.1696 0.574 Uiso 1 1 calc R . . H37B H 0.6627 0.1749 0.1336 0.574 Uiso 1 1 calc R . . H37C H 0.7125 0.2637 0.1370 0.574 Uiso 1 1 calc R . . O1 O 0.9215(2) 0.6025(2) 0.16921(9) 0.0907(9) Uani 1 1 d . . . O2 O 0.5189(3) 0.3493(2) 0.17423(10) 0.1177(13) Uani 1 1 d . . . O3 O 0.51868(19) 0.8344(2) 0.18916(8) 0.0905(9) Uani 1 1 d . . . O4 O 0.7242(3) 0.3998(4) 0.02723(9) 0.1356(18) Uani 1 1 d . . . O5 O 0.4558(2) 0.5863(2) 0.04505(7) 0.0888(9) Uani 1 1 d . . . O6 O 0.7445(2) 0.8326(2) 0.03879(7) 0.0934(10) Uani 1 1 d . . . O7 O 0.6540(4) 0.6540(4) 0.0000 0.348(11) Uani 1 2 d SU . . O8 O 0.0594(9) 0.5469(8) 0.2318(5) 0.401(10) Uani 1 1 d U . . O9 O 0.6725(15) 0.3275(15) 0.2500 0.471(17) Uani 1 2 d SU . . 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 C28A 0.137(7) 0.142(9) 0.302(16) 0.056(10) 0.117(9) -0.023(7) C29A 0.134(7) 0.173(9) 0.331(15) 0.042(9) 0.106(9) -0.014(7) C30A 0.150(9) 0.263(14) 0.389(19) 0.062(15) 0.131(11) -0.042(10) C28B 0.21(2) 0.090(14) 0.062(10) 0.041(8) 0.079(10) 0.075(13) C29B 0.215(19) 0.119(13) 0.065(10) 0.031(8) 0.090(11) 0.058(12) C30B 0.21(2) 0.177(19) 0.094(13) 0.033(13) 0.090(13) 0.056(16) C1 0.073(3) 0.071(3) 0.057(2) -0.0006(19) -0.003(2) -0.003(2) C2 0.085(3) 0.056(2) 0.066(2) -0.0006(18) -0.011(2) -0.003(2) C3 0.072(3) 0.066(2) 0.070(2) 0.0002(19) 0.000(2) -0.0039(19) C4 0.074(3) 0.071(3) 0.071(2) -0.006(2) 0.003(2) -0.001(2) C5 0.079(3) 0.065(2) 0.070(2) -0.004(2) 0.000(2) -0.0113(19) C6 0.092(3) 0.054(2) 0.069(2) 0.0043(18) 0.003(2) -0.007(2) C7 0.101(3) 0.066(3) 0.063(2) -0.0007(19) 0.005(2) -0.009(2) C8 0.072(3) 0.109(4) 0.070(3) -0.013(2) 0.000(2) 0.007(2) C9 0.096(3) 0.062(3) 0.072(2) 0.003(2) 0.017(2) -0.017(2) C10 0.070(2) 0.069(2) 0.068(2) 0.003(2) 0.009(2) -0.0059(19) C11 0.075(3) 0.067(2) 0.073(3) -0.013(2) 0.017(2) -0.013(2) C12 0.060(2) 0.066(2) 0.064(2) -0.0058(19) 0.0088(17) -0.0019(17) C13 0.0465(18) 0.061(2) 0.075(2) -0.0011(18) 0.0127(17) -0.0032(16) C14 0.050(2) 0.072(2) 0.068(2) -0.006(2) 0.0106(17) -0.0024(17) C15 0.061(2) 0.082(3) 0.073(2) 0.000(2) 0.011(2) -0.006(2) C16 0.080(3) 0.063(3) 0.067(2) -0.009(2) 0.012(2) -0.009(2) C17 0.056(2) 0.070(2) 0.071(2) -0.0098(19) 0.0051(19) 0.0004(18) C18 0.056(2) 0.062(2) 0.067(2) -0.0106(18) 0.0114(17) -0.0108(17) C19 0.0472(18) 0.062(2) 0.068(2) 0.0006(17) 0.0032(16) -0.0061(16) C20 0.0461(18) 0.071(2) 0.059(2) -0.0019(17) -0.0056(16) 0.0011(17) C21 0.0488(19) 0.072(2) 0.0569(19) -0.0063(18) -0.0052(16) -0.0047(17) C22 0.059(2) 0.055(2) 0.065(2) 0.0014(17) -0.0035(17) -0.0090(16) C23 0.072(2) 0.074(3) 0.067(2) -0.005(2) 0.010(2) -0.021(2) C24 0.059(2) 0.079(2) 0.059(2) -0.0065(19) -0.0056(18) 0.008(2) C25 0.117(4) 0.081(3) 0.158(5) 0.003(3) -0.048(4) -0.006(3) C26 0.155(7) 0.124(6) 0.254(10) 0.002(6) 0.026(7) 0.041(5) C27 0.35(2) 0.166(10) 0.48(2) -0.022(12) -0.117(17) 0.128(12) C31 0.129(5) 0.093(4) 0.202(5) -0.065(4) 0.100(4) -0.039(3) C32 0.253(12) 0.263(11) 0.315(9) -0.181(9) -0.194(11) 0.105(10) C33 0.42(2) 0.251(13) 0.338(15) -0.126(14) -0.114(17) -0.001(15) N1 0.086(2) 0.059(2) 0.078(2) 0.0039(16) -0.0201(19) 0.0001(17) N2 0.090(3) 0.082(3) 0.081(2) 0.012(2) 0.024(2) -0.016(2) N3 0.064(2) 0.071(2) 0.084(2) -0.0160(18) 0.0179(17) -0.0113(16) N4 0.086(3) 0.110(3) 0.065(2) -0.012(2) 0.0021(19) 0.006(2) N5 0.100(3) 0.068(2) 0.0639(19) -0.0029(17) 0.0115(18) 0.0024(18) N6 0.076(2) 0.105(3) 0.0634(18) 0.0106(19) 0.0016(17) 0.027(2) N7 0.233(10) 0.387(16) 0.095(4) -0.016(7) 0.021(5) -0.011(11) C34 0.206(10) 0.258(13) 0.133(7) 0.011(9) 0.035(8) -0.061(9) C35 0.41(2) 0.206(11) 0.191(9) -0.049(8) 0.086(11) -0.184(13) N8 0.41(3) 0.286(19) 0.50(3) 0.060(18) 0.13(2) 0.143(18) C36 0.41(3) 0.162(12) 0.320(18) -0.005(13) -0.02(2) 0.007(15) C37 0.253(18) 0.30(2) 0.60(3) -0.04(2) -0.17(2) 0.100(17) O1 0.094(2) 0.0684(18) 0.110(2) 0.0048(17) -0.035(2) -0.0072(16) O2 0.153(3) 0.077(2) 0.123(3) 0.025(2) 0.044(3) -0.014(2) O3 0.0661(17) 0.106(2) 0.100(2) -0.0334(19) 0.0277(16) -0.0108(16) O4 0.090(3) 0.242(5) 0.075(2) -0.022(3) -0.002(2) 0.043(3) O5 0.118(3) 0.077(2) 0.0710(17) -0.0089(16) -0.0002(16) 0.0014(17) O6 0.102(2) 0.111(2) 0.0669(16) 0.0084(17) 0.0019(16) 0.046(2) O7 0.343(14) 0.343(14) 0.357(15) -0.139(13) 0.139(13) -0.264(15) O8 0.323(14) 0.279(12) 0.60(2) 0.065(14) -0.271(16) -0.079(11) O9 0.51(2) 0.51(2) 0.40(3) -0.123(19) -0.123(19) 0.01(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 C28A C29A 1.48(2) . ? C28A N2 1.560(14) . ? C28A H28A 0.9700 . ? C28A H28B 0.9700 . ? C29A C30A 1.509(16) . ? C29A H29A 0.9700 . ? C29A H29B 0.9700 . ? C30A H30A 0.9600 . ? C30A H30B 0.9600 . ? C30A H30C 0.9600 . ? C28B N2 1.44(3) . ? C28B C29B 1.47(3) . ? C28B H28C 0.9700 . ? C28B H28D 0.9700 . ? C29B C30B 1.55(2) . ? C29B H29C 0.9700 . ? C29B H29D 0.9700 . ? C30B H30D 0.9600 . ? C30B H30E 0.9600 . ? C30B H30F 0.9600 . ? C1 O1 1.236(5) . ? C1 N1 1.336(6) . ? C1 C22 1.510(6) . ? C2 C3 1.377(6) . ? C2 C7 1.378(6) . ? C2 N1 1.411(5) . ? C3 C4 1.356(6) . ? C3 H3 0.9300 . ? C4 C5 1.389(6) . ? C4 C8 1.493(6) . ? C5 C6 1.396(6) . ? C5 H5 0.9300 . ? C6 C7 1.372(6) . ? C6 C9 1.492(6) . ? C7 H7 0.9300 . ? C8 O4 1.232(6) . ? C8 N4 1.318(6) . ? C9 O2 1.237(5) . ? C9 N2 1.351(6) . ? C10 C11 1.378(6) . ? C10 C15 1.387(6) . ? C10 N2 1.415(6) . ? C11 C12 1.389(6) . ? C11 H11 0.9300 . ? C12 C13 1.371(5) . ? C12 C16 1.499(6) . ? C13 C14 1.394(6) . ? C13 H13 0.9300 . ? C14 C15 1.362(6) . ? C14 C17 1.498(6) . ? C15 H15 0.9300 . ? C16 O5 1.235(5) . ? C16 N5 1.289(5) . ? C17 O3 1.240(5) . ? C17 N3 1.306(5) . ? C18 C23 1.359(6) . ? C18 C19 1.371(6) . ? C18 N3 1.441(5) . ? C19 C20 1.382(5) . ? C19 H19 0.9300 . ? C20 C21 1.402(6) . ? C20 C24 1.495(6) . ? C21 C22 1.378(5) . ? C21 H21 0.9300 . ? C22 C23 1.397(6) . ? C23 H23 0.9300 . ? C24 O6 1.233(5) . ? C24 N6 1.313(5) . ? C25 C26 1.455(11) . ? C25 N1 1.480(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.668(15) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C31 N3 1.517(6) . ? C31 C32 1.762(15) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.562(18) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? N7 C34 1.216(14) . ? C34 C35 1.426(15) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? N8 C36 1.282(19) . ? C36 C37 1.463(19) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? 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 C29A C28A N2 108.2(14) . . ? C29A C28A H28A 110.1 . . ? N2 C28A H28A 110.1 . . ? C29A C28A H28B 110.1 . . ? N2 C28A H28B 110.1 . . ? H28A C28A H28B 108.4 . . ? C28A C29A C30A 104.5(14) . . ? C28A C29A H29A 110.9 . . ? C30A C29A H29A 110.9 . . ? C28A C29A H29B 110.9 . . ? C30A C29A H29B 110.9 . . ? H29A C29A H29B 108.9 . . ? C29A C30A H30A 109.5 . . ? C29A C30A H30B 109.5 . . ? H30A C30A H30B 109.5 . . ? C29A C30A H30C 109.5 . . ? H30A C30A H30C 109.5 . . ? H30B C30A H30C 109.5 . . ? N2 C28B C29B 121(3) . . ? N2 C28B H28C 107.1 . . ? C29B C28B H28C 107.1 . . ? N2 C28B H28D 107.1 . . ? C29B C28B H28D 107.1 . . ? H28C C28B H28D 106.8 . . ? C28B C29B C30B 96(2) . . ? C28B C29B H29C 112.5 . . ? C30B C29B H29C 112.5 . . ? C28B C29B H29D 112.5 . . ? C30B C29B H29D 112.5 . . ? H29C C29B H29D 110.0 . . ? C29B C30B H30D 109.5 . . ? C29B C30B H30E 109.5 . . ? H30D C30B H30E 109.5 . . ? C29B C30B H30F 109.5 . . ? H30D C30B H30F 109.5 . . ? H30E C30B H30F 109.5 . . ? O1 C1 N1 123.4(4) . . ? O1 C1 C22 118.6(4) . . ? N1 C1 C22 118.0(3) . . ? C3 C2 C7 119.3(4) . . ? C3 C2 N1 121.4(4) . . ? C7 C2 N1 119.2(4) . . ? C4 C3 C2 120.8(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 C8 120.1(4) . . ? C5 C4 C8 119.4(4) . . ? C4 C5 C6 119.1(4) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C7 C6 C5 119.5(4) . . ? C7 C6 C9 120.0(4) . . ? C5 C6 C9 120.5(4) . . ? C6 C7 C2 120.8(4) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? O4 C8 N4 121.8(4) . . ? O4 C8 C4 119.3(4) . . ? N4 C8 C4 118.9(4) . . ? O2 C9 N2 123.4(4) . . ? O2 C9 C6 119.3(4) . . ? N2 C9 C6 117.2(4) . . ? C11 C10 C15 118.9(4) . . ? C11 C10 N2 120.4(4) . . ? C15 C10 N2 120.7(4) . . ? C10 C11 C12 121.4(4) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 118.6(4) . . ? C13 C12 C16 123.1(4) . . ? C11 C12 C16 118.2(4) . . ? C12 C13 C14 120.4(4) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.2(4) . . ? C15 C14 C17 119.9(4) . . ? C13 C14 C17 119.7(4) . . ? C14 C15 C10 120.3(4) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? O5 C16 N5 124.2(4) . . ? O5 C16 C12 118.1(4) . . ? N5 C16 C12 117.7(4) . . ? O3 C17 N3 122.0(4) . . ? O3 C17 C14 119.2(3) . . ? N3 C17 C14 118.7(3) . . ? C23 C18 C19 120.6(3) . . ? C23 C18 N3 119.6(4) . . ? C19 C18 N3 119.8(4) . . ? C18 C19 C20 120.5(4) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C21 119.3(3) . . ? C19 C20 C24 118.4(3) . . ? C21 C20 C24 122.2(3) . . ? C22 C21 C20 119.6(3) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 119.8(4) . . ? C21 C22 C1 118.2(3) . . ? C23 C22 C1 121.3(3) . . ? C18 C23 C22 120.1(4) . . ? C18 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? O6 C24 N6 121.1(4) . . ? O6 C24 C20 119.3(3) . . ? N6 C24 C20 119.6(4) . . ? C26 C25 N1 111.5(6) . . ? C26 C25 H25A 109.3 . . ? N1 C25 H25A 109.3 . . ? C26 C25 H25B 109.3 . . ? N1 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C27 102.2(10) . . ? C25 C26 H26A 111.3 . . ? C27 C26 H26A 111.3 . . ? C25 C26 H26B 111.3 . . ? C27 C26 H26B 111.3 . . ? H26A C26 H26B 109.2 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N3 C31 C32 108.0(6) . . ? N3 C31 H31A 110.1 . . ? C32 C31 H31A 110.1 . . ? N3 C31 H31B 110.1 . . ? C32 C31 H31B 110.1 . . ? H31A C31 H31B 108.4 . . ? C33 C32 C31 103.2(12) . . ? C33 C32 H32A 111.1 . . ? C31 C32 H32A 111.1 . . ? C33 C32 H32B 111.1 . . ? C31 C32 H32B 111.1 . . ? H32A C32 H32B 109.1 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C1 N1 C2 123.9(3) . . ? C1 N1 C25 118.0(4) . . ? C2 N1 C25 117.0(4) . . ? C9 N2 C10 120.8(3) . . ? C9 N2 C28B 119.6(12) . . ? C10 N2 C28B 119.0(11) . . ? C9 N2 C28A 121.7(7) . . ? C10 N2 C28A 117.5(7) . . ? C28B N2 C28A 8.3(19) . . ? C17 N3 C18 122.1(3) . . ? C17 N3 C31 120.9(4) . . ? C18 N3 C31 116.4(3) . . ? C8 N4 H4A 120.0 . . ? C8 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C16 N5 H5A 120.0 . . ? C16 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C24 N6 H6A 120.0 . . ? C24 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? N7 C34 C35 161.0(13) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N8 C36 C37 175(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 . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.437 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.077 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.267 0.267 0.000 171 42 ' ' 2 -0.233 0.233 0.250 171 42 ' ' 3 0.009 0.394 0.391 23 4 ' ' 4 -0.267 0.733 0.500 171 42 ' ' 5 0.233 0.767 0.750 171 43 ' ' 6 -0.009 0.606 0.891 23 4 ' ' 7 0.070 0.693 0.280 13 3 ' ' 8 0.106 0.509 0.141 23 4 ' ' 9 0.197 0.262 0.187 15 2 ' ' 10 0.193 0.429 0.530 13 3 ' ' 11 0.238 0.698 0.937 15 2 ' ' 12 0.262 0.198 0.813 15 2 ' ' 13 0.302 0.762 0.563 15 2 ' ' 14 0.307 0.929 0.220 12 3 ' ' 15 0.394 0.009 0.608 23 4 ' ' 16 0.429 0.193 0.470 13 3 ' ' 17 0.491 0.894 0.359 23 4 ' ' 18 0.509 0.106 0.859 23 4 ' ' 19 0.570 0.807 0.970 13 3 ' ' 20 0.606 0.991 0.109 23 4 ' ' 21 0.697 0.238 0.063 15 2 ' ' 22 0.693 0.070 0.720 13 3 ' ' 23 0.738 0.802 0.313 15 2 ' ' 24 0.762 0.302 0.437 15 2 ' ' 25 0.802 0.738 0.687 15 2 ' ' 26 0.807 0.571 0.030 13 3 ' ' 27 0.894 0.491 0.641 23 4 ' ' 28 0.929 0.307 0.780 12 3 ' ' _platon_squeeze_details ; ;