# CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_global _audit_creation_method 'maXus' _publ_contact_author_name 'N. Cramer' _publ_contact_author_address ; ; _publ_contact_author_email 'nicolai.cramer@org.chem.ethz.ch' _publ_contact_author_fax ' ' _publ_contact_author_phone ' ' _publ_section_title ; Crystal and molecular structure of ca030610 ; _publ_section_abstract ; We present the crystal and molecular structure of ca030610 ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'LOC ETH Zurich' _exptl_crystal_description 'needle' _exptl_crystal_size_max .36 _exptl_crystal_size_mid .06 _exptl_crystal_size_min .024 _exptl_crystal_F_000 476.0 _exptl_crystal_colour 'pale yellow' _diffrn_ambient_temperature 100 _cell_measurement_temperature 100 _refine_ls_hydrogen_treatment 'refall' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 -0.12382 _diffrn_orient_matrix_UB_12 0.04133 _diffrn_orient_matrix_UB_13 0.02188 _diffrn_orient_matrix_UB_21 0.05352 _diffrn_orient_matrix_UB_22 0.07007 _diffrn_orient_matrix_UB_23 0.02968 _diffrn_orient_matrix_UB_31 -0.00299 _diffrn_orient_matrix_UB_32 0.00241 _diffrn_orient_matrix_UB_33 -0.07791 _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 449.507 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' _symmetry_space_group_name_H-M 'P -1 ' _symmetry_cell_setting 'Triclinic' _chemical_formula_moiety 'C25 H27 N3 O5 ' _chemical_formula_sum 'C25 H27 N3 O5 ' _chemical_name_systematic ; ? ; _cell_length_a 7.9939(5) _cell_length_b 11.9064(9) _cell_length_c 13.8485(12) _cell_angle_alpha 68.816(3) _cell_angle_beta 77.480(4) _cell_angle_gamma 72.174(3) _cell_volume 1161.6(2) _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_number 6601 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_full 24.97 _cell_measurement_reflns_used 24651 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _diffrn_reflns_av_R_equivalents 0.060 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_absorpt_coefficient_mu 0.091 _reflns_number_total 4009 _reflns_number_gt 3001 _reflns_threshold_expression >2sigma(I) _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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4009 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1708 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 O12 O -0.2216(3) 0.70223(19) 0.86440(15) 0.0392(5) Uani 1 1 d . . . O13 O -0.6087(2) 0.82298(15) 0.62314(14) 0.0290(4) Uani 1 1 d . . . O21 O -0.3866(2) 0.75717(15) 0.41484(14) 0.0290(4) Uani 1 1 d . . . O24 O 0.0558(2) 0.87233(15) 0.34437(13) 0.0282(4) Uani 1 1 d . . . O33 O 0.2440(3) 0.50094(16) 0.52415(14) 0.0296(4) Uani 1 1 d . . . N1 N -0.4573(3) 0.75797(19) 0.76788(16) 0.0267(5) Uani 1 1 d . . . N3 N -0.3028(3) 0.73599(18) 0.61798(16) 0.0241(5) Uani 1 1 d . . . N4 N -0.1844(3) 0.69354(18) 0.69627(16) 0.0253(5) Uani 1 1 d . . . C2 C -0.4721(4) 0.7795(2) 0.66336(19) 0.0255(6) Uani 1 1 d . . . C5 C -0.2804(4) 0.7172(2) 0.7857(2) 0.0294(6) Uani 1 1 d . . . C6 C -0.6039(4) 0.7813(2) 0.8446(2) 0.0307(6) Uani 1 1 d . . . C7 C -0.7366(4) 0.7208(3) 0.8661(2) 0.0355(7) Uani 1 1 d . . . C8 C -0.8783(4) 0.7432(3) 0.9404(2) 0.0412(7) Uani 1 1 d . . . C9 C -0.8862(4) 0.8248(3) 0.9929(2) 0.0423(7) Uani 1 1 d . . . C10 C -0.7519(4) 0.8847(3) 0.9703(2) 0.0411(7) Uani 1 1 d . . . C11 C -0.6098(4) 0.8631(2) 0.8957(2) 0.0327(6) Uani 1 1 d . . . C14 C -0.2211(3) 0.8073(2) 0.51340(19) 0.0242(6) Uani 1 1 d . . . C15 C -0.0500(3) 0.7119(2) 0.48912(19) 0.0245(6) Uani 1 1 d . . . C16 C 0.0797(4) 0.6783(2) 0.5700(2) 0.0251(6) Uani 1 1 d . . . C17 C -0.0181(4) 0.7377(2) 0.6547(2) 0.0258(6) Uani 1 1 d . . . C18 C -0.0724(4) 0.8768(2) 0.6045(2) 0.0268(6) Uani 1 1 d . . . C19 C -0.1758(4) 0.9128(2) 0.5308(2) 0.0257(6) Uani 1 1 d . . . C20 C -0.3485(4) 0.8567(2) 0.4322(2) 0.0256(6) Uani 1 1 d . . . C22 C -0.5111(4) 0.8031(3) 0.3407(3) 0.0381(7) Uani 1 1 d . . . C23 C 0.0294(4) 0.7507(2) 0.3754(2) 0.0267(6) Uani 1 1 d . . . C25 C 0.1020(5) 0.9179(3) 0.2347(2) 0.0367(7) Uani 1 1 d . . . C26 C 0.1512(3) 0.5372(2) 0.6131(2) 0.0243(6) Uani 1 1 d . . . C27 C 0.2696(3) 0.4953(2) 0.6981(2) 0.0262(6) Uani 1 1 d . . . C28 C 0.2141(4) 0.4329(3) 0.8008(2) 0.0340(6) Uani 1 1 d . . . C29 C 0.3249(5) 0.3903(3) 0.8777(2) 0.0422(7) Uani 1 1 d . . . C30 C 0.4931(4) 0.4092(3) 0.8526(2) 0.0395(7) Uani 1 1 d . . . C31 C 0.5512(4) 0.4716(2) 0.7507(2) 0.0305(6) Uani 1 1 d . . . C32 C 0.4399(4) 0.5140(2) 0.6738(2) 0.0276(6) Uani 1 1 d . . . H7 H -0.730(4) 0.662(3) 0.828(3) 0.047(9) Uiso 1 1 d . . . H8 H -0.968(5) 0.699(3) 0.958(3) 0.054(10) Uiso 1 1 d . . . H9 H -0.987(5) 0.842(3) 1.046(3) 0.057(10) Uiso 1 1 d . . . H10 H -0.760(6) 0.949(4) 1.005(3) 0.075(12) Uiso 1 1 d . . . H11 H -0.509(5) 0.901(3) 0.880(3) 0.045(9) Uiso 1 1 d . . . H15 H -0.085(3) 0.631(2) 0.4971(19) 0.020(6) Uiso 1 1 d . . . H16 H 0.179(4) 0.714(3) 0.535(2) 0.037(8) Uiso 1 1 d . . . H17 H 0.048(3) 0.714(2) 0.7147(19) 0.013(6) Uiso 1 1 d . . . H18 H -0.036(4) 0.928(3) 0.629(2) 0.031(7) Uiso 1 1 d . . . H19 H -0.232(4) 1.001(3) 0.488(2) 0.033(7) Uiso 1 1 d . . . H20A H -0.295(4) 0.908(3) 0.367(2) 0.030(7) Uiso 1 1 d . . . H20B H -0.460(3) 0.912(2) 0.4520(18) 0.012(6) Uiso 1 1 d . . . H22A H -0.454(4) 0.863(3) 0.270(3) 0.045(9) Uiso 1 1 d . . . H22B H -0.539(5) 0.733(3) 0.329(3) 0.052(9) Uiso 1 1 d . . . H22C H -0.625(5) 0.852(3) 0.370(3) 0.049(9) Uiso 1 1 d . . . H23A H -0.047(3) 0.7473(19) 0.3329(18) 0.007(5) Uiso 1 1 d . . . H23B H 0.152(4) 0.693(2) 0.363(2) 0.023(6) Uiso 1 1 d . . . H25A H 0.123(4) 0.998(3) 0.222(2) 0.030(7) Uiso 1 1 d . . . H25B H 0.213(5) 0.861(3) 0.207(3) 0.052(10) Uiso 1 1 d . . . H25C H 0.004(5) 0.932(3) 0.188(3) 0.059(10) Uiso 1 1 d . . . H26 H 0.050(3) 0.499(2) 0.6422(18) 0.013(6) Uiso 1 1 d . . . H28 H 0.088(5) 0.418(3) 0.820(2) 0.043(8) Uiso 1 1 d . . . H29 H 0.282(4) 0.346(3) 0.949(3) 0.044(8) Uiso 1 1 d . . . H30 H 0.577(5) 0.375(3) 0.908(3) 0.052(9) Uiso 1 1 d . . . H31 H 0.673(4) 0.484(3) 0.728(2) 0.028(7) Uiso 1 1 d . . . H32 H 0.478(4) 0.557(3) 0.603(3) 0.038(8) Uiso 1 1 d . . . H33 H 0.288(5) 0.407(4) 0.551(3) 0.065(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O12 0.0354(12) 0.0541(12) 0.0274(10) -0.0150(9) -0.0056(9) -0.0067(10) O13 0.0263(10) 0.0261(9) 0.0301(10) -0.0062(7) -0.0063(8) -0.0018(8) O21 0.0306(11) 0.0224(9) 0.0366(10) -0.0104(8) -0.0131(8) -0.0028(8) O24 0.0337(11) 0.0254(9) 0.0243(9) -0.0058(7) -0.0047(8) -0.0073(8) O33 0.0322(11) 0.0260(9) 0.0304(10) -0.0113(8) -0.0066(8) -0.0022(8) N1 0.0258(12) 0.0264(11) 0.0258(11) -0.0082(9) -0.0047(9) -0.0027(9) N3 0.0252(12) 0.0222(10) 0.0238(11) -0.0058(8) -0.0068(9) -0.0038(9) N4 0.0246(12) 0.0269(11) 0.0230(11) -0.0059(9) -0.0064(9) -0.0043(9) C2 0.0311(15) 0.0161(11) 0.0258(13) -0.0039(9) -0.0038(11) -0.0042(11) C5 0.0310(15) 0.0272(13) 0.0285(14) -0.0079(11) -0.0042(12) -0.0058(11) C6 0.0276(15) 0.0307(13) 0.0270(14) -0.0074(11) -0.0026(11) -0.0004(11) C7 0.0304(16) 0.0429(16) 0.0325(15) -0.0130(13) -0.0049(12) -0.0061(13) C8 0.0314(17) 0.0558(18) 0.0331(16) -0.0107(14) -0.0047(13) -0.0100(15) C9 0.0333(17) 0.0543(18) 0.0292(15) -0.0152(14) -0.0029(13) 0.0048(14) C10 0.048(2) 0.0360(15) 0.0338(16) -0.0129(13) -0.0085(14) 0.0011(14) C11 0.0370(17) 0.0282(13) 0.0300(14) -0.0079(11) -0.0075(12) -0.0034(13) C14 0.0260(14) 0.0195(11) 0.0255(13) -0.0063(10) -0.0038(11) -0.0042(10) C15 0.0231(14) 0.0210(12) 0.0293(14) -0.0089(10) -0.0065(11) -0.0020(10) C16 0.0263(14) 0.0212(12) 0.0277(13) -0.0070(10) -0.0056(11) -0.0050(11) C17 0.0262(14) 0.0246(12) 0.0270(14) -0.0087(10) -0.0053(11) -0.0049(11) C18 0.0311(15) 0.0247(12) 0.0284(14) -0.0127(11) -0.0020(11) -0.0083(11) C19 0.0278(14) 0.0224(12) 0.0272(13) -0.0097(10) -0.0016(11) -0.0055(11) C20 0.0289(15) 0.0201(12) 0.0277(14) -0.0085(11) -0.0052(11) -0.0035(12) C22 0.0396(18) 0.0339(15) 0.0481(18) -0.0160(14) -0.0238(15) -0.0030(14) C23 0.0287(15) 0.0266(13) 0.0253(13) -0.0087(10) -0.0062(11) -0.0049(12) C25 0.0446(19) 0.0380(16) 0.0256(14) -0.0046(12) -0.0040(13) -0.0145(15) C26 0.0236(14) 0.0222(12) 0.0276(13) -0.0079(10) -0.0055(11) -0.0049(11) C27 0.0263(14) 0.0220(12) 0.0287(14) -0.0067(10) -0.0054(11) -0.0040(11) C28 0.0328(16) 0.0343(14) 0.0308(15) -0.0038(12) -0.0070(12) -0.0081(13) C29 0.049(2) 0.0424(17) 0.0293(16) -0.0014(13) -0.0074(14) -0.0130(15) C30 0.0438(19) 0.0339(15) 0.0383(17) -0.0062(13) -0.0163(14) -0.0048(14) C31 0.0293(16) 0.0275(13) 0.0375(15) -0.0135(11) -0.0065(12) -0.0055(12) C32 0.0293(15) 0.0224(12) 0.0309(14) -0.0093(11) -0.0042(12) -0.0047(11) _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 O12 C5 1.213(3) . ? O13 C2 1.217(3) . ? O21 C20 1.419(3) . ? O21 C22 1.431(3) . ? O24 C25 1.422(3) . ? O24 C23 1.423(3) . ? O33 C26 1.431(3) . ? N1 C5 1.393(4) . ? N1 C2 1.401(3) . ? N1 C6 1.433(3) . ? N3 C2 1.390(3) . ? N3 N4 1.443(3) . ? N3 C14 1.512(3) . ? N4 C5 1.382(4) . ? N4 C17 1.501(3) . ? C6 C11 1.380(4) . ? C6 C7 1.381(4) . ? C7 C8 1.386(4) . ? C8 C9 1.389(5) . ? C9 C10 1.387(5) . ? C10 C11 1.389(4) . ? C14 C20 1.517(4) . ? C14 C19 1.518(3) . ? C14 C15 1.549(4) . ? C15 C23 1.523(4) . ? C15 C16 1.554(3) . ? C16 C26 1.530(3) . ? C16 C17 1.534(4) . ? C17 C18 1.507(3) . ? C18 C19 1.319(4) . ? C26 C27 1.516(3) . ? C27 C28 1.391(4) . ? C27 C32 1.396(4) . ? C28 C29 1.386(4) . ? C29 C30 1.380(4) . ? C30 C31 1.389(4) . ? C31 C32 1.389(4) . ? O33 H33 1.01(4) . ? C7 H7 1.00(3) . ? C8 H8 0.96(4) . ? C9 H9 0.99(4) . ? C10 H10 1.01(4) . ? C11 H11 0.99(3) . ? C15 H15 1.05(2) . ? C16 H16 0.97(3) . ? C17 H17 0.99(2) . ? C18 H18 0.93(3) . ? C19 H19 1.01(3) . ? C20 H20A 0.98(3) . ? C20 H20B 0.99(3) . ? C22 H22A 1.08(3) . ? C22 H22B 1.00(3) . ? C22 H22C 1.01(4) . ? C23 H23A 0.95(2) . ? C23 H23B 1.03(3) . ? C25 H25A 0.97(3) . ? C25 H25B 1.03(4) . ? C25 H25C 1.06(4) . ? C26 H26 0.99(2) . ? C28 H28 1.03(3) . ? C29 H29 0.98(3) . ? C30 H30 1.02(4) . ? C31 H31 0.99(3) . ? C32 H32 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 O21 C22 110.88(19) . . ? C25 O24 C23 111.20(19) . . ? C5 N1 C2 110.8(2) . . ? C5 N1 C6 124.6(2) . . ? C2 N1 C6 124.5(2) . . ? C2 N3 N4 107.5(2) . . ? C2 N3 C14 123.73(19) . . ? N4 N3 C14 111.02(18) . . ? C5 N4 N3 108.5(2) . . ? C5 N4 C17 117.7(2) . . ? N3 N4 C17 112.29(18) . . ? O13 C2 N3 127.8(2) . . ? O13 C2 N1 125.8(2) . . ? N3 C2 N1 106.3(2) . . ? O12 C5 N4 126.5(3) . . ? O12 C5 N1 127.3(3) . . ? N4 C5 N1 106.1(2) . . ? C11 C6 C7 121.3(3) . . ? C11 C6 N1 119.6(2) . . ? C7 C6 N1 119.0(2) . . ? C6 C7 C8 119.0(3) . . ? C7 C8 C9 120.5(3) . . ? C10 C9 C8 119.7(3) . . ? C9 C10 C11 120.1(3) . . ? C6 C11 C10 119.3(3) . . ? N3 C14 C20 111.1(2) . . ? N3 C14 C19 106.08(19) . . ? C20 C14 C19 111.11(19) . . ? N3 C14 C15 103.79(18) . . ? C20 C14 C15 113.9(2) . . ? C19 C14 C15 110.4(2) . . ? C23 C15 C14 113.0(2) . . ? C23 C15 C16 115.2(2) . . ? C14 C15 C16 109.7(2) . . ? C26 C16 C17 113.2(2) . . ? C26 C16 C15 110.63(19) . . ? C17 C16 C15 107.9(2) . . ? N4 C17 C18 107.3(2) . . ? N4 C17 C16 106.85(19) . . ? C18 C17 C16 108.6(2) . . ? C19 C18 C17 113.9(2) . . ? C18 C19 C14 114.4(2) . . ? O21 C20 C14 110.56(19) . . ? O24 C23 C15 110.6(2) . . ? O33 C26 C27 111.5(2) . . ? O33 C26 C16 104.7(2) . . ? C27 C26 C16 114.3(2) . . ? C28 C27 C32 118.7(2) . . ? C28 C27 C26 120.9(2) . . ? C32 C27 C26 120.4(2) . . ? C29 C28 C27 120.9(3) . . ? C30 C29 C28 119.9(3) . . ? C29 C30 C31 120.2(3) . . ? C32 C31 C30 119.7(3) . . ? C31 C32 C27 120.6(2) . . ? C26 O33 H33 105(2) . . ? C6 C7 H7 120.3(19) . . ? C8 C7 H7 120.7(19) . . ? C7 C8 H8 120(2) . . ? C9 C8 H8 120(2) . . ? C10 C9 H9 119(2) . . ? C8 C9 H9 122(2) . . ? C9 C10 H10 121(2) . . ? C11 C10 H10 119(2) . . ? C6 C11 H11 119(2) . . ? C10 C11 H11 122(2) . . ? C23 C15 H15 102.5(14) . . ? C14 C15 H15 107.7(15) . . ? C16 C15 H15 108.1(14) . . ? C26 C16 H16 108.0(18) . . ? C17 C16 H16 108.7(17) . . ? C15 C16 H16 108.3(18) . . ? N4 C17 H17 107.1(14) . . ? C18 C17 H17 112.1(13) . . ? C16 C17 H17 114.6(15) . . ? C19 C18 H18 126.5(18) . . ? C17 C18 H18 119.5(18) . . ? C18 C19 H19 128.0(16) . . ? C14 C19 H19 117.6(16) . . ? O21 C20 H20A 110.3(16) . . ? C14 C20 H20A 108.5(17) . . ? O21 C20 H20B 109.4(13) . . ? C14 C20 H20B 112.3(14) . . ? H20A C20 H20B 106(2) . . ? O21 C22 H22A 106.9(17) . . ? O21 C22 H22B 111(2) . . ? H22A C22 H22B 113(3) . . ? O21 C22 H22C 108.7(19) . . ? H22A C22 H22C 111(3) . . ? H22B C22 H22C 107(3) . . ? O24 C23 H23A 110.7(13) . . ? C15 C23 H23A 109.3(13) . . ? O24 C23 H23B 106.3(14) . . ? C15 C23 H23B 111.6(14) . . ? H23A C23 H23B 108.3(19) . . ? O24 C25 H25A 104.8(17) . . ? O24 C25 H25B 113.3(19) . . ? H25A C25 H25B 110(3) . . ? O24 C25 H25C 116(2) . . ? H25A C25 H25C 107(3) . . ? H25B C25 H25C 105(3) . . ? O33 C26 H26 109.6(13) . . ? C27 C26 H26 108.1(14) . . ? C16 C26 H26 108.5(14) . . ? C29 C28 H28 119.4(18) . . ? C27 C28 H28 119.8(18) . . ? C30 C29 H29 121.4(19) . . ? C28 C29 H29 119(2) . . ? C29 C30 H30 120(2) . . ? C31 C30 H30 120(2) . . ? C32 C31 H31 117.2(16) . . ? C30 C31 H31 123.0(16) . . ? C31 C32 H32 120.6(19) . . ? C27 C32 H32 118.8(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N3 N4 C5 -2.9(2) . . . . ? C14 N3 N4 C5 135.2(2) . . . . ? C2 N3 N4 C17 -134.7(2) . . . . ? C14 N3 N4 C17 3.4(2) . . . . ? N4 N3 C2 O13 -180.0(2) . . . . ? C14 N3 C2 O13 48.5(3) . . . . ? N4 N3 C2 N1 -2.9(2) . . . . ? C14 N3 C2 N1 -134.3(2) . . . . ? C5 N1 C2 O13 -175.1(2) . . . . ? C6 N1 C2 O13 1.8(4) . . . . ? C5 N1 C2 N3 7.7(3) . . . . ? C6 N1 C2 N3 -175.4(2) . . . . ? N3 N4 C5 O12 -174.1(2) . . . . ? C17 N4 C5 O12 -45.3(4) . . . . ? N3 N4 C5 N1 7.4(2) . . . . ? C17 N4 C5 N1 136.3(2) . . . . ? C2 N1 C5 O12 172.1(2) . . . . ? C6 N1 C5 O12 -4.8(4) . . . . ? C2 N1 C5 N4 -9.5(3) . . . . ? C6 N1 C5 N4 173.7(2) . . . . ? C5 N1 C6 C11 55.4(3) . . . . ? C2 N1 C6 C11 -121.0(3) . . . . ? C5 N1 C6 C7 -124.4(3) . . . . ? C2 N1 C6 C7 59.2(3) . . . . ? C11 C6 C7 C8 0.0(4) . . . . ? N1 C6 C7 C8 179.9(2) . . . . ? C6 C7 C8 C9 -0.3(4) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C7 C6 C11 C10 0.2(4) . . . . ? N1 C6 C11 C10 -179.7(2) . . . . ? C9 C10 C11 C6 -0.2(4) . . . . ? C2 N3 C14 C20 -47.5(3) . . . . ? N4 N3 C14 C20 -177.55(19) . . . . ? C2 N3 C14 C19 73.3(3) . . . . ? N4 N3 C14 C19 -56.7(2) . . . . ? C2 N3 C14 C15 -170.3(2) . . . . ? N4 N3 C14 C15 59.7(2) . . . . ? N3 C14 C15 C23 164.63(19) . . . . ? C20 C14 C15 C23 43.8(3) . . . . ? C19 C14 C15 C23 -82.1(2) . . . . ? N3 C14 C15 C16 -65.3(2) . . . . ? C20 C14 C15 C16 173.82(19) . . . . ? C19 C14 C15 C16 48.0(3) . . . . ? C23 C15 C16 C26 -99.0(2) . . . . ? C14 C15 C16 C26 132.1(2) . . . . ? C23 C15 C16 C17 136.7(2) . . . . ? C14 C15 C16 C17 7.8(2) . . . . ? C5 N4 C17 C18 -74.5(3) . . . . ? N3 N4 C17 C18 52.5(3) . . . . ? C5 N4 C17 C16 169.2(2) . . . . ? N3 N4 C17 C16 -63.8(2) . . . . ? C26 C16 C17 N4 -68.0(3) . . . . ? C15 C16 C17 N4 54.7(2) . . . . ? C26 C16 C17 C18 176.5(2) . . . . ? C15 C16 C17 C18 -60.7(2) . . . . ? N4 C17 C18 C19 -56.3(3) . . . . ? C16 C17 C18 C19 58.8(3) . . . . ? C17 C18 C19 C14 1.1(3) . . . . ? N3 C14 C19 C18 55.9(3) . . . . ? C20 C14 C19 C18 176.7(2) . . . . ? C15 C14 C19 C18 -56.0(3) . . . . ? C22 O21 C20 C14 178.2(2) . . . . ? N3 C14 C20 O21 -63.5(3) . . . . ? C19 C14 C20 O21 178.7(2) . . . . ? C15 C14 C20 O21 53.2(3) . . . . ? C25 O24 C23 C15 -170.3(2) . . . . ? C14 C15 C23 O24 53.6(3) . . . . ? C16 C15 C23 O24 -73.6(3) . . . . ? C17 C16 C26 O33 -177.2(2) . . . . ? C15 C16 C26 O33 61.5(3) . . . . ? C17 C16 C26 C27 -54.9(3) . . . . ? C15 C16 C26 C27 -176.1(2) . . . . ? O33 C26 C27 C28 -130.8(2) . . . . ? C16 C26 C27 C28 110.7(3) . . . . ? O33 C26 C27 C32 46.4(3) . . . . ? C16 C26 C27 C32 -72.1(3) . . . . ? C32 C27 C28 C29 0.3(4) . . . . ? C26 C27 C28 C29 177.5(3) . . . . ? C27 C28 C29 C30 -0.4(4) . . . . ? C28 C29 C30 C31 0.6(5) . . . . ? C29 C30 C31 C32 -0.6(4) . . . . ? C30 C31 C32 C27 0.5(4) . . . . ? C28 C27 C32 C31 -0.3(4) . . . . ? C26 C27 C32 C31 -177.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.232 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.048 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ;