# 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 'Azumaya, Isao' _publ_contact_author_email azumayai@kph.bunri-u.ac.jp _publ_section_title ; Crystal Structure of Spherical Aromatic Amide: Pseudopolymorphs and Formation of Infinite Water Cluster in the Channel Structure ; loop_ _publ_author_name H.Masu K.Katagiri M.Kawahata M.Tominaga H.Kagechika ; K.Yamaguchi ; I.Azumaya # Attachment '- CIF_azumaya_re.cif' data_1a(a1002091mas2) _database_code_depnum_ccdc_archive 'CCDC 661900' #TrackingRef '- CIF_azumaya_re.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H42 N6 O12' _chemical_formula_weight 750.76 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 9.207(1) _cell_length_b 24.232(3) _cell_length_c 17.811(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.068(5) _cell_angle_gamma 90.00 _cell_volume 3628.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 2732 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 22.11 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9896 _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 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17735 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0735 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.39 _reflns_number_total 7352 _reflns_number_gt 4547 _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^)+(0.0800P)^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 7352 _refine_ls_number_parameters 494 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1670 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 O1 O 0.2164(2) 0.70792(8) 0.38216(11) 0.0270(5) Uani 1 1 d . . . O2 O -0.4886(2) 0.83895(11) 0.39707(13) 0.0496(7) Uani 1 1 d . . . O3 O -0.2762(2) 0.92901(8) 0.71126(12) 0.0304(5) Uani 1 1 d . . . O4 O -0.1453(2) 0.68534(8) 0.67780(13) 0.0339(5) Uani 1 1 d . . . O5 O 0.7210(2) 0.81003(8) 0.82068(12) 0.0304(5) Uani 1 1 d . . . O6 O 0.2836(3) 1.01852(8) 0.55420(12) 0.0359(5) Uani 1 1 d . . . N1 N 0.3744(3) 0.72450(9) 0.51654(13) 0.0219(5) Uani 1 1 d . . . N2 N -0.2624(3) 0.83388(9) 0.37592(13) 0.0228(5) Uani 1 1 d . . . N3 N -0.0134(3) 0.94146(9) 0.74208(14) 0.0237(5) Uani 1 1 d . . . N4 N 0.1109(3) 0.70176(9) 0.70202(13) 0.0202(5) Uani 1 1 d . . . N5 N 0.5207(3) 0.86967(9) 0.80694(13) 0.0213(5) Uani 1 1 d . . . N6 N 0.2352(3) 0.93789(9) 0.48451(14) 0.0229(5) Uani 1 1 d . . . C1 C 0.2340(3) 0.94149(10) 0.62156(16) 0.0199(6) Uani 1 1 d . . . C2 C 0.2282(3) 0.73001(10) 0.68210(16) 0.0196(6) Uani 1 1 d . . . C3 C 0.2473(3) 0.96930(11) 0.54930(17) 0.0230(6) Uani 1 1 d . . . C4 C 0.4607(3) 0.78782(10) 0.72178(16) 0.0202(6) Uani 1 1 d . . . C5 C 0.1090(3) 0.95139(11) 0.64449(17) 0.0223(6) Uani 1 1 d . . . H5 H 0.0181 0.9713 0.6090 0.027 Uiso 1 1 calc R . . C6 C 0.1177(3) 0.93202(11) 0.71935(17) 0.0213(6) Uani 1 1 d . . . C7 C 0.4777(3) 0.77357(11) 0.65005(16) 0.0212(6) Uani 1 1 d . . . H7 H 0.5655 0.7869 0.6403 0.025 Uiso 1 1 calc R . . C8 C -0.0111(3) 0.88422(12) 0.43713(16) 0.0229(6) Uani 1 1 d . . . H8 H -0.0686 0.9169 0.4362 0.027 Uiso 1 1 calc R . . C9 C 0.2502(3) 0.73655(11) 0.44428(17) 0.0220(6) Uani 1 1 d . . . C10 C 0.3651(3) 0.73973(11) 0.59308(16) 0.0215(6) Uani 1 1 d . . . C11 C 0.1580(3) 0.78810(11) 0.44270(16) 0.0203(6) Uani 1 1 d . . . C12 C -0.0947(3) 0.77202(11) 0.63426(17) 0.0221(6) Uani 1 1 d . . . C13 C -0.0433(3) 0.71633(11) 0.67219(16) 0.0221(6) Uani 1 1 d . . . C14 C 0.2524(3) 0.90534(11) 0.77369(17) 0.0224(6) Uani 1 1 d . . . H14 H 0.2599 0.8942 0.8263 0.027 Uiso 1 1 calc R . . C15 C -0.3432(3) 0.83334(12) 0.42431(18) 0.0268(7) Uani 1 1 d . . . C16 C 0.5798(3) 0.82394(11) 0.78585(16) 0.0214(6) Uani 1 1 d . . . C17 C -0.0073(3) 0.78672(11) 0.41008(16) 0.0219(6) Uani 1 1 d . . . H17 H -0.0627 0.7534 0.3884 0.026 Uiso 1 1 calc R . . C18 C 0.3356(3) 0.76586(11) 0.73787(16) 0.0209(6) Uani 1 1 d . . . H18 H 0.3244 0.7755 0.7869 0.025 Uiso 1 1 calc R . . C19 C -0.2488(3) 0.82664(11) 0.51494(17) 0.0225(6) Uani 1 1 d . . . C20 C 0.3767(3) 0.89502(11) 0.75038(16) 0.0203(6) Uani 1 1 d . . . C21 C 0.3667(3) 0.91242(10) 0.67418(16) 0.0211(6) Uani 1 1 d . . . H21 H 0.4508 0.9045 0.6579 0.025 Uiso 1 1 calc R . . C22 C 0.2392(3) 0.83752(11) 0.47035(15) 0.0210(6) Uani 1 1 d . . . H22 H 0.3521 0.8384 0.4919 0.025 Uiso 1 1 calc R . . C23 C -0.0801(3) 0.81762(11) 0.68454(16) 0.0210(6) Uani 1 1 d . . . H23 H -0.0186 0.8150 0.7421 0.025 Uiso 1 1 calc R . . C24 C -0.2420(3) 0.87098(11) 0.56598(17) 0.0226(6) Uani 1 1 d . . . H24 H -0.2970 0.9042 0.5429 0.027 Uiso 1 1 calc R . . C25 C -0.1553(3) 0.86690(11) 0.65038(16) 0.0204(6) Uani 1 1 d . . . C26 C 0.2419(3) 0.71692(11) 0.60921(17) 0.0223(6) Uani 1 1 d . . . H26 H 0.1678 0.6926 0.5707 0.027 Uiso 1 1 calc R . . C27 C 0.6253(3) 0.90376(12) 0.87571(17) 0.0287(7) Uani 1 1 d . . . H27A H 0.6915 0.8799 0.9212 0.043 Uiso 1 1 calc R . . H27B H 0.5607 0.9279 0.8941 0.043 Uiso 1 1 calc R . . H27C H 0.6937 0.9263 0.8578 0.043 Uiso 1 1 calc R . . C28 C -0.0904(3) 0.83463(11) 0.40954(16) 0.0214(6) Uani 1 1 d . . . C29 C 0.1606(3) 0.64829(11) 0.74386(18) 0.0284(7) Uani 1 1 d . . . H29A H 0.0872 0.6375 0.7685 0.043 Uiso 1 1 calc R . . H29B H 0.2684 0.6515 0.7870 0.043 Uiso 1 1 calc R . . H29C H 0.1592 0.6203 0.7039 0.043 Uiso 1 1 calc R . . C30 C -0.1537(3) 0.91518(11) 0.70320(17) 0.0237(6) Uani 1 1 d . . . C31 C 0.1541(3) 0.88534(11) 0.46621(16) 0.0212(6) Uani 1 1 d . . . C32 C -0.3461(3) 0.84371(13) 0.28723(17) 0.0305(7) Uani 1 1 d . . . H32A H -0.4604 0.8377 0.2703 0.046 Uiso 1 1 calc R . . H32B H -0.3061 0.8182 0.2574 0.046 Uiso 1 1 calc R . . H32C H -0.3277 0.8818 0.2748 0.046 Uiso 1 1 calc R . . C33 C 0.2837(4) 0.95950(12) 0.42099(18) 0.0302(7) Uani 1 1 d . . . H33A H 0.1889 0.9693 0.3719 0.045 Uiso 1 1 calc R . . H33B H 0.3444 0.9312 0.4068 0.045 Uiso 1 1 calc R . . H33C H 0.3500 0.9924 0.4420 0.045 Uiso 1 1 calc R . . C34 C -0.1770(3) 0.77693(12) 0.54957(17) 0.0243(6) Uani 1 1 d . . . H34 H -0.1842 0.7462 0.5151 0.029 Uiso 1 1 calc R . . C35 C 0.4773(4) 0.67727(12) 0.52014(19) 0.0323(7) Uani 1 1 d . . . H35A H 0.4245 0.6430 0.5241 0.048 Uiso 1 1 calc R . . H35B H 0.5784 0.6809 0.5684 0.048 Uiso 1 1 calc R . . H35C H 0.4976 0.6765 0.4703 0.048 Uiso 1 1 calc R . . C36 C 0.0042(4) 0.98524(12) 0.80261(18) 0.0332(7) Uani 1 1 d . . . H36A H -0.0117 1.0213 0.7756 0.050 Uiso 1 1 calc R . . H36B H 0.1112 0.9835 0.8469 0.050 Uiso 1 1 calc R . . H36C H -0.0751 0.9800 0.8256 0.050 Uiso 1 1 calc R . . O7 O 0.8060(3) 0.90911(10) 0.07999(15) 0.0552(7) Uani 1 1 d . . . O8 O 1.0019(3) 0.63266(9) 0.40980(14) 0.0475(6) Uani 1 1 d . . . O9 O 0.0367(3) 0.94603(9) 0.02878(14) 0.0453(6) Uani 1 1 d . . . O10 O 0.4232(3) 0.96756(9) 0.28549(14) 0.0484(6) Uani 1 1 d . . . O11 O 0.3623(3) 0.93145(11) 0.12759(16) 0.0647(8) Uani 1 1 d . . . O12 O 0.5775(4) 0.98104(11) 0.07862(18) 0.0728(8) Uani 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 O1 0.0277(12) 0.0325(11) 0.0228(11) -0.0058(9) 0.0125(9) -0.0014(9) O2 0.0194(13) 0.100(2) 0.0300(12) 0.0079(13) 0.0108(10) 0.0103(13) O3 0.0200(11) 0.0358(12) 0.0392(12) -0.0013(10) 0.0159(10) 0.0035(9) O4 0.0248(12) 0.0318(12) 0.0491(14) 0.0089(10) 0.0191(11) -0.0024(10) O5 0.0194(11) 0.0306(11) 0.0360(12) -0.0028(9) 0.0061(9) 0.0041(9) O6 0.0551(15) 0.0221(11) 0.0382(13) 0.0006(9) 0.0269(12) -0.0032(10) N1 0.0203(13) 0.0257(12) 0.0213(12) -0.0016(10) 0.0101(10) 0.0020(10) N2 0.0168(13) 0.0310(13) 0.0220(12) -0.0005(10) 0.0096(10) -0.0008(10) N3 0.0172(13) 0.0296(13) 0.0269(13) -0.0054(10) 0.0118(11) -0.0009(10) N4 0.0161(12) 0.0215(12) 0.0247(13) 0.0029(10) 0.0102(10) -0.0007(10) N5 0.0170(12) 0.0221(12) 0.0220(12) -0.0024(10) 0.0052(10) 0.0002(10) N6 0.0245(14) 0.0222(12) 0.0270(13) -0.0009(10) 0.0157(11) -0.0037(10) C1 0.0197(15) 0.0167(13) 0.0246(15) -0.0018(11) 0.0104(12) -0.0018(11) C2 0.0172(15) 0.0167(13) 0.0271(15) 0.0034(11) 0.0113(12) 0.0016(11) C3 0.0201(16) 0.0210(15) 0.0278(15) 0.0012(12) 0.0097(13) 0.0010(12) C4 0.0168(14) 0.0208(14) 0.0221(14) 0.0022(11) 0.0073(12) 0.0019(12) C5 0.0178(15) 0.0209(14) 0.0273(15) 0.0000(12) 0.0083(12) 0.0020(12) C6 0.0175(15) 0.0223(14) 0.0257(15) -0.0040(12) 0.0106(12) -0.0005(12) C7 0.0155(14) 0.0229(14) 0.0249(15) 0.0032(12) 0.0082(12) 0.0009(12) C8 0.0217(16) 0.0273(15) 0.0226(15) 0.0003(12) 0.0120(12) 0.0016(12) C9 0.0216(16) 0.0248(15) 0.0228(15) -0.0013(12) 0.0122(12) -0.0047(12) C10 0.0202(15) 0.0236(15) 0.0224(15) 0.0020(12) 0.0103(12) 0.0036(12) C11 0.0194(15) 0.0239(14) 0.0188(14) 0.0005(11) 0.0090(12) 0.0003(12) C12 0.0160(15) 0.0265(15) 0.0270(15) 0.0034(12) 0.0122(12) 0.0003(12) C13 0.0218(16) 0.0250(15) 0.0235(15) -0.0010(12) 0.0131(13) -0.0025(13) C14 0.0232(16) 0.0239(14) 0.0226(15) -0.0008(12) 0.0119(12) -0.0019(12) C15 0.0204(16) 0.0340(17) 0.0276(16) 0.0018(13) 0.0117(13) 0.0010(13) C16 0.0201(16) 0.0246(15) 0.0209(15) 0.0010(12) 0.0098(13) -0.0011(12) C17 0.0208(15) 0.0250(15) 0.0206(14) -0.0040(12) 0.0091(12) -0.0038(12) C18 0.0202(15) 0.0219(14) 0.0207(14) -0.0006(11) 0.0086(12) 0.0009(12) C19 0.0143(15) 0.0311(16) 0.0254(15) 0.0024(12) 0.0116(12) 0.0005(12) C20 0.0138(14) 0.0215(14) 0.0228(14) -0.0015(11) 0.0046(12) -0.0008(11) C21 0.0198(15) 0.0209(14) 0.0262(15) -0.0035(12) 0.0130(13) -0.0008(12) C22 0.0163(14) 0.0298(16) 0.0176(14) 0.0012(12) 0.0077(12) -0.0009(12) C23 0.0130(14) 0.0290(16) 0.0204(14) 0.0027(12) 0.0062(12) -0.0007(12) C24 0.0164(15) 0.0258(15) 0.0290(16) 0.0048(12) 0.0126(12) 0.0004(12) C25 0.0155(14) 0.0241(14) 0.0237(15) 0.0018(12) 0.0100(12) -0.0021(12) C26 0.0180(15) 0.0206(14) 0.0250(15) -0.0001(12) 0.0054(12) 0.0011(12) C27 0.0238(17) 0.0312(17) 0.0272(16) -0.0068(13) 0.0064(13) 0.0001(13) C28 0.0165(15) 0.0287(15) 0.0199(14) 0.0012(12) 0.0083(12) 0.0005(12) C29 0.0263(17) 0.0261(15) 0.0310(17) 0.0061(13) 0.0101(14) -0.0009(13) C30 0.0199(16) 0.0276(15) 0.0255(15) 0.0043(12) 0.0113(13) 0.0017(12) C31 0.0220(16) 0.0246(15) 0.0203(14) -0.0001(12) 0.0119(12) -0.0048(12) C32 0.0246(17) 0.0427(19) 0.0229(16) -0.0004(14) 0.0083(13) -0.0017(14) C33 0.0369(19) 0.0290(16) 0.0310(16) 0.0016(13) 0.0202(15) -0.0059(14) C34 0.0190(15) 0.0289(15) 0.0278(16) -0.0031(13) 0.0124(13) -0.0019(13) C35 0.0297(18) 0.0362(18) 0.0321(17) -0.0033(14) 0.0138(14) 0.0096(14) C36 0.0316(19) 0.0353(17) 0.0354(18) -0.0104(14) 0.0163(15) 0.0005(14) O7 0.0540(17) 0.0568(16) 0.0495(15) 0.0040(13) 0.0157(13) -0.0059(13) O8 0.0357(14) 0.0414(14) 0.0606(16) 0.0167(12) 0.0148(12) 0.0006(11) O9 0.0448(15) 0.0472(14) 0.0436(14) -0.0056(11) 0.0177(12) -0.0046(12) O10 0.0524(16) 0.0437(14) 0.0507(15) -0.0063(12) 0.0226(13) -0.0022(12) O11 0.0623(19) 0.0743(19) 0.0587(17) -0.0070(15) 0.0258(15) 0.0029(15) O12 0.070(2) 0.0654(19) 0.082(2) 0.0001(16) 0.0293(17) 0.0059(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.234(3) . ? O2 C15 1.232(3) . ? O3 C30 1.239(3) . ? O4 C13 1.238(3) . ? O5 C16 1.237(3) . ? O6 C3 1.232(3) . ? N1 C9 1.360(3) . ? N1 C10 1.448(3) . ? N1 C35 1.470(3) . ? N2 C15 1.349(3) . ? N2 C28 1.447(3) . ? N2 C32 1.467(3) . ? N3 C30 1.351(3) . ? N3 C6 1.439(3) . ? N3 C36 1.474(3) . ? N4 C13 1.344(3) . ? N4 C2 1.440(3) . ? N4 C29 1.471(3) . ? N5 C16 1.354(3) . ? N5 C20 1.435(3) . ? N5 C27 1.466(3) . ? N6 C3 1.349(3) . ? N6 C31 1.444(3) . ? N6 C33 1.472(3) . ? C1 C5 1.390(4) . ? C1 C21 1.391(4) . ? C1 C3 1.501(4) . ? C2 C18 1.385(4) . ? C2 C26 1.391(4) . ? C4 C7 1.392(4) . ? C4 C18 1.401(4) . ? C4 C16 1.500(4) . ? C5 C6 1.385(4) . ? C5 H5 0.9500 . ? C6 C14 1.384(4) . ? C7 C10 1.385(4) . ? C7 H7 0.9500 . ? C8 C28 1.388(4) . ? C8 C31 1.393(4) . ? C8 H8 0.9500 . ? C9 C11 1.504(4) . ? C10 C26 1.393(4) . ? C11 C17 1.390(4) . ? C11 C22 1.391(4) . ? C12 C34 1.390(4) . ? C12 C23 1.394(4) . ? C12 C13 1.497(4) . ? C14 C20 1.390(4) . ? C14 H14 0.9500 . ? C15 C19 1.498(4) . ? C17 C28 1.389(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C34 1.391(4) . ? C19 C24 1.392(4) . ? C20 C21 1.388(4) . ? C21 H21 0.9500 . ? C22 C31 1.384(4) . ? C22 H22 0.9500 . ? C23 C25 1.390(4) . ? C23 H23 0.9500 . ? C24 C25 1.389(4) . ? C24 H24 0.9500 . ? C25 C30 1.498(4) . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34 0.9500 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? 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 C9 N1 C10 119.1(2) . . ? C9 N1 C35 119.1(2) . . ? C10 N1 C35 116.2(2) . . ? C15 N2 C28 122.1(2) . . ? C15 N2 C32 120.3(2) . . ? C28 N2 C32 116.7(2) . . ? C30 N3 C6 121.2(2) . . ? C30 N3 C36 120.7(2) . . ? C6 N3 C36 117.7(2) . . ? C13 N4 C2 123.7(2) . . ? C13 N4 C29 119.4(2) . . ? C2 N4 C29 115.7(2) . . ? C16 N5 C20 121.1(2) . . ? C16 N5 C27 119.4(2) . . ? C20 N5 C27 116.7(2) . . ? C3 N6 C31 123.1(2) . . ? C3 N6 C33 120.8(2) . . ? C31 N6 C33 115.5(2) . . ? C5 C1 C21 119.7(2) . . ? C5 C1 C3 122.8(2) . . ? C21 C1 C3 116.7(2) . . ? C18 C2 C26 120.1(2) . . ? C18 C2 N4 120.6(2) . . ? C26 C2 N4 119.0(2) . . ? O6 C3 N6 122.2(2) . . ? O6 C3 C1 119.2(2) . . ? N6 C3 C1 118.2(2) . . ? C7 C4 C18 120.2(2) . . ? C7 C4 C16 121.5(2) . . ? C18 C4 C16 118.2(2) . . ? C6 C5 C1 119.7(3) . . ? C6 C5 H5 120.2 . . ? C1 C5 H5 120.2 . . ? C14 C6 C5 121.0(2) . . ? C14 C6 N3 119.5(2) . . ? C5 C6 N3 119.4(2) . . ? C10 C7 C4 119.2(3) . . ? C10 C7 H7 120.4 . . ? C4 C7 H7 120.4 . . ? C28 C8 C31 119.1(3) . . ? C28 C8 H8 120.5 . . ? C31 C8 H8 120.5 . . ? O1 C9 N1 122.4(2) . . ? O1 C9 C11 121.1(2) . . ? N1 C9 C11 116.5(2) . . ? C7 C10 C26 120.9(3) . . ? C7 C10 N1 121.7(2) . . ? C26 C10 N1 117.3(2) . . ? C17 C11 C22 120.5(3) . . ? C17 C11 C9 120.1(2) . . ? C22 C11 C9 119.4(2) . . ? C34 C12 C23 119.8(3) . . ? C34 C12 C13 119.9(2) . . ? C23 C12 C13 119.7(2) . . ? O4 C13 N4 121.5(3) . . ? O4 C13 C12 118.2(2) . . ? N4 C13 C12 120.3(2) . . ? C6 C14 C20 119.2(3) . . ? C6 C14 H14 120.4 . . ? C20 C14 H14 120.4 . . ? O2 C15 N2 122.8(3) . . ? O2 C15 C19 119.8(3) . . ? N2 C15 C19 117.4(2) . . ? O5 C16 N5 122.9(2) . . ? O5 C16 C4 121.0(2) . . ? N5 C16 C4 115.9(2) . . ? C28 C17 C11 119.3(3) . . ? C28 C17 H17 120.4 . . ? C11 C17 H17 120.4 . . ? C2 C18 C4 119.9(2) . . ? C2 C18 H18 120.1 . . ? C4 C18 H18 120.1 . . ? C34 C19 C24 119.5(3) . . ? C34 C19 C15 122.3(3) . . ? C24 C19 C15 118.1(2) . . ? C21 C20 C14 120.2(3) . . ? C21 C20 N5 119.3(2) . . ? C14 C20 N5 120.3(2) . . ? C20 C21 C1 120.2(2) . . ? C20 C21 H21 119.9 . . ? C1 C21 H21 119.9 . . ? C31 C22 C11 119.4(2) . . ? C31 C22 H22 120.3 . . ? C11 C22 H22 120.3 . . ? C25 C23 C12 120.0(2) . . ? C25 C23 H23 120.0 . . ? C12 C23 H23 120.0 . . ? C25 C24 C19 120.3(3) . . ? C25 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? C24 C25 C23 119.9(3) . . ? C24 C25 C30 118.6(2) . . ? C23 C25 C30 121.4(2) . . ? C2 C26 C10 119.6(3) . . ? C2 C26 H26 120.2 . . ? C10 C26 H26 120.2 . . ? N5 C27 H27A 109.5 . . ? N5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C8 C28 C17 120.8(3) . . ? C8 C28 N2 119.1(2) . . ? C17 C28 N2 120.0(2) . . ? N4 C29 H29A 109.5 . . ? N4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O3 C30 N3 122.6(3) . . ? O3 C30 C25 120.5(3) . . ? N3 C30 C25 116.9(2) . . ? C22 C31 C8 120.8(3) . . ? C22 C31 N6 119.8(2) . . ? C8 C31 N6 119.1(2) . . ? N2 C32 H32A 109.5 . . ? N2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N6 C33 H33A 109.5 . . ? N6 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N6 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C12 C34 C19 120.4(3) . . ? C12 C34 H34 119.8 . . ? C19 C34 H34 119.8 . . ? N1 C35 H35A 109.5 . . ? N1 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N1 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N3 C36 H36A 109.5 . . ? N3 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? N3 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.518 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.062 # Attachment '779155.cif' data_1b(a1002221mas4) _database_code_depnum_ccdc_archive 'CCDC 779155' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H39 N9 O6' _chemical_formula_weight 765.82 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 9.133(3) _cell_length_b 19.628(6) _cell_length_c 22.662(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.77(1) _cell_angle_gamma 90.00 _cell_volume 3869(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 2072 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 21.64 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9955 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18504 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.1069 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.20 _reflns_number_total 7781 _reflns_number_gt 4052 _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^)+(0.0595P)^2^+4.4070P] 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 SHELXL _refine_ls_extinction_coef 0.0053(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7781 _refine_ls_number_parameters 535 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1482 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1905 _refine_ls_wR_factor_gt 0.1649 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0009(3) 0.60001(14) 0.67266(13) 0.0394(7) Uani 1 1 d . . . O2 O 0.9078(3) 0.65640(15) 0.41888(13) 0.0413(8) Uani 1 1 d . . . O3 O 0.9123(4) 0.90023(15) 0.56917(15) 0.0537(9) Uani 1 1 d . . . O4 O 0.2707(3) 0.50661(13) 0.46777(12) 0.0329(7) Uani 1 1 d . . . O5 O 0.0452(5) 0.8676(2) 0.42775(16) 0.0823(13) Uani 1 1 d . . . O6 O 0.3017(4) 0.75073(16) 0.75007(14) 0.0552(9) Uani 1 1 d . . . N1 N 0.7799(4) 0.62827(16) 0.69372(14) 0.0297(8) Uani 1 1 d . . . N2 N 0.6493(3) 0.66635(16) 0.39339(14) 0.0283(8) Uani 1 1 d . . . N3 N 0.6730(4) 0.90102(16) 0.57630(16) 0.0394(9) Uani 1 1 d . . . N4 N 0.2771(3) 0.56965(15) 0.55274(13) 0.0248(7) Uani 1 1 d . . . N5 N 0.1872(3) 0.78619(15) 0.40118(14) 0.0263(7) Uani 1 1 d . . . N6 N 0.2900(4) 0.81933(19) 0.66959(16) 0.0443(10) Uani 1 1 d . . . C1 C 0.8367(4) 0.68025(19) 0.60545(17) 0.0268(9) Uani 1 1 d . . . C2 C 0.8341(4) 0.6542(2) 0.54772(17) 0.0289(9) Uani 1 1 d . . . H2 H 0.8541 0.6073 0.5435 0.035 Uiso 1 1 calc R . . C3 C 0.8024(4) 0.69682(19) 0.49674(17) 0.0272(9) Uani 1 1 d . . . C4 C 0.7858(4) 0.7661(2) 0.50396(18) 0.0306(9) Uani 1 1 d . . . H4 H 0.7694 0.7956 0.4693 0.037 Uiso 1 1 calc R . . C5 C 0.7927(4) 0.79304(19) 0.56156(18) 0.0282(9) Uani 1 1 d . . . C6 C 0.8150(4) 0.74925(19) 0.61222(18) 0.0277(9) Uani 1 1 d . . . H6 H 0.8153 0.7669 0.6513 0.033 Uiso 1 1 calc R . . C7 C 0.8791(4) 0.6328(2) 0.65943(18) 0.0304(9) Uani 1 1 d . . . C8 C 0.8168(6) 0.5838(2) 0.7483(2) 0.0382(11) Uani 1 1 d . . . C9 C 0.7913(4) 0.67046(18) 0.43340(17) 0.0283(9) Uani 1 1 d . . . C10 C 0.6264(5) 0.6505(2) 0.32804(17) 0.0412(11) Uani 1 1 d . . . H10A H 0.6103 0.6014 0.3213 0.062 Uiso 1 1 calc R . . H10B H 0.7175 0.6645 0.3168 0.062 Uiso 1 1 calc R . . H10C H 0.5362 0.6752 0.3022 0.062 Uiso 1 1 calc R . . C11 C 0.7964(5) 0.8683(2) 0.56918(19) 0.0379(10) Uani 1 1 d . . . C12 C 0.6817(7) 0.9744(2) 0.5871(3) 0.0637(16) Uani 1 1 d . . . H12A H 0.6759 0.9981 0.5484 0.096 Uiso 1 1 calc R . . H12B H 0.7792 0.9856 0.6185 0.096 Uiso 1 1 calc R . . H12C H 0.5959 0.9888 0.6016 0.096 Uiso 1 1 calc R . . C13 C 0.6198(4) 0.64463(19) 0.66751(17) 0.0294(9) Uani 1 1 d . . . C14 C 0.5295(4) 0.6049(2) 0.61945(17) 0.0276(9) Uani 1 1 d . . . H14 H 0.5752 0.5705 0.6014 0.033 Uiso 1 1 calc R . . C15 C 0.3717(4) 0.61584(18) 0.59797(17) 0.0266(9) Uani 1 1 d . . . C16 C 0.3046(4) 0.66609(19) 0.62319(17) 0.0281(9) Uani 1 1 d . . . H16 H 0.1966 0.6733 0.6083 0.034 Uiso 1 1 calc R . . C17 C 0.3960(5) 0.7064(2) 0.67073(17) 0.0308(9) Uani 1 1 d . . . C18 C 0.5541(4) 0.6948(2) 0.69354(18) 0.0303(9) Uani 1 1 d . . . H18 H 0.6159 0.7215 0.7269 0.036 Uiso 1 1 calc R . . C19 C 0.1979(5) 0.51623(19) 0.57734(18) 0.0323(10) Uani 1 1 d . . . H19A H 0.2733 0.4827 0.6004 0.048 Uiso 1 1 calc R . . H19B H 0.1215 0.4936 0.5429 0.048 Uiso 1 1 calc R . . H19C H 0.1465 0.5369 0.6051 0.048 Uiso 1 1 calc R . . C20 C 0.3016(4) 0.56067(19) 0.49670(17) 0.0252(9) Uani 1 1 d . . . C21 C 0.5147(4) 0.67008(19) 0.41413(16) 0.0250(8) Uani 1 1 d . . . C22 C 0.4202(4) 0.72681(18) 0.39907(16) 0.0243(8) Uani 1 1 d . . . H22 H 0.4420 0.7624 0.3746 0.029 Uiso 1 1 calc R . . C23 C 0.2931(4) 0.73072(18) 0.42034(16) 0.0238(8) Uani 1 1 d . . . C24 C 0.2620(4) 0.67867(18) 0.45643(16) 0.0236(8) Uani 1 1 d . . . H24 H 0.1775 0.6827 0.4724 0.028 Uiso 1 1 calc R . . C25 C 0.3543(4) 0.62071(18) 0.46923(16) 0.0228(8) Uani 1 1 d . . . C26 C 0.4808(4) 0.61659(19) 0.44735(16) 0.0255(9) Uani 1 1 d . . . H26 H 0.5438 0.5770 0.4553 0.031 Uiso 1 1 calc R . . C27 C 0.0751(5) 0.7797(2) 0.33946(18) 0.0372(10) Uani 1 1 d . . . H27A H 0.0212 0.8231 0.3275 0.056 Uiso 1 1 calc R . . H27B H 0.0006 0.7440 0.3401 0.056 Uiso 1 1 calc R . . H27C H 0.1285 0.7676 0.3094 0.056 Uiso 1 1 calc R . . C28 C 0.1594(5) 0.8307(2) 0.44218(19) 0.0393(11) Uani 1 1 d . . . C29 C 0.5269(5) 0.8696(2) 0.56940(19) 0.0353(10) Uani 1 1 d . . . C30 C 0.4818(5) 0.8569(2) 0.62176(19) 0.0387(11) Uani 1 1 d . . . H30 H 0.5514 0.8644 0.6620 0.046 Uiso 1 1 calc R . . C31 C 0.3348(5) 0.8335(2) 0.61473(19) 0.0387(11) Uani 1 1 d . . . C32 C 0.2306(5) 0.8249(2) 0.55710(19) 0.0367(10) Uani 1 1 d . . . H32 H 0.1280 0.8116 0.5531 0.044 Uiso 1 1 calc R . . C33 C 0.2752(5) 0.8355(2) 0.50489(19) 0.0365(10) Uani 1 1 d . . . C34 C 0.4242(5) 0.85724(19) 0.51099(19) 0.0362(10) Uani 1 1 d . . . H34 H 0.4557 0.8637 0.4751 0.043 Uiso 1 1 calc R . . C35 C 0.2189(7) 0.8746(3) 0.6947(2) 0.0747(18) Uani 1 1 d . . . H35A H 0.1239 0.8891 0.6634 0.112 Uiso 1 1 calc R . . H35B H 0.2901 0.9132 0.7058 0.112 Uiso 1 1 calc R . . H35C H 0.1951 0.8585 0.7317 0.112 Uiso 1 1 calc R . . C36 C 0.3257(5) 0.7601(2) 0.70031(19) 0.0352(10) Uani 1 1 d . . . N7 N -0.1442(5) 0.8832(3) 0.7291(2) 0.0767(15) Uani 1 1 d . . . C37 C -0.0564(5) 0.9042(3) 0.7723(2) 0.0438(11) Uani 1 1 d . . . C38 C 0.0551(5) 0.9298(2) 0.8281(2) 0.0451(12) Uani 1 1 d . . . H38A H 0.1586 0.9159 0.8286 0.068 Uiso 1 1 calc R . . H38B H 0.0327 0.9111 0.8645 0.068 Uiso 1 1 calc R . . H38C H 0.0493 0.9796 0.8288 0.068 Uiso 1 1 calc R . . N8 N 0.4847(7) 0.5007(3) 0.7528(3) 0.099(2) Uani 1 1 d . . . C39 C 0.4053(7) 0.5398(3) 0.7657(2) 0.0606(15) Uani 1 1 d . . . C40 C 0.3103(6) 0.5884(3) 0.7834(2) 0.0610(14) Uani 1 1 d . . . H40A H 0.3599 0.6332 0.7884 0.092 Uiso 1 1 calc R . . H40B H 0.2953 0.5744 0.8227 0.092 Uiso 1 1 calc R . . H40C H 0.2104 0.5909 0.7512 0.092 Uiso 1 1 calc R . . N9 N 0.6155(6) 0.6041(3) 0.9020(2) 0.0952(19) Uani 1 1 d . . . C41 C 0.7087(6) 0.5626(3) 0.9141(3) 0.0594(14) Uani 1 1 d . . . C42 C 0.8250(7) 0.5131(3) 0.9306(3) 0.0815(19) Uani 1 1 d . . . H42A H 0.7945 0.4766 0.9540 0.122 Uiso 1 1 calc R . . H42B H 0.9207 0.5339 0.9563 0.122 Uiso 1 1 calc R . . H42C H 0.8410 0.4940 0.8931 0.122 Uiso 1 1 calc R . . H8A H 0.777(4) 0.6063(18) 0.7845(17) 0.030(10) Uiso 1 1 d . . . H8B H 0.760(5) 0.540(2) 0.7396(17) 0.035(11) Uiso 1 1 d . . . H8C H 0.918(7) 0.575(3) 0.766(3) 0.09(2) 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 O1 0.0290(16) 0.0424(17) 0.0439(18) 0.0047(14) 0.0071(14) 0.0090(14) O2 0.0221(15) 0.062(2) 0.0438(18) -0.0143(15) 0.0156(14) -0.0029(14) O3 0.058(2) 0.0342(17) 0.074(2) -0.0121(16) 0.0278(19) -0.0099(16) O4 0.0384(17) 0.0248(15) 0.0345(16) -0.0036(12) 0.0094(13) -0.0008(12) O5 0.086(3) 0.099(3) 0.053(2) -0.006(2) 0.008(2) 0.074(3) O6 0.076(2) 0.060(2) 0.042(2) -0.0114(16) 0.0359(18) -0.0077(18) N1 0.0264(18) 0.0333(19) 0.0272(18) 0.0004(15) 0.0048(15) -0.0013(15) N2 0.0207(17) 0.042(2) 0.0228(17) -0.0039(15) 0.0077(14) 0.0035(15) N3 0.050(2) 0.0264(19) 0.045(2) -0.0078(16) 0.0191(19) 0.0005(18) N4 0.0249(17) 0.0239(17) 0.0253(18) -0.0017(13) 0.0074(14) -0.0070(14) N5 0.0267(17) 0.0257(17) 0.0268(18) 0.0057(14) 0.0086(15) 0.0107(14) N6 0.049(2) 0.056(3) 0.035(2) -0.0002(18) 0.0228(19) 0.023(2) C1 0.0186(19) 0.030(2) 0.032(2) -0.0022(17) 0.0076(17) -0.0027(17) C2 0.022(2) 0.029(2) 0.037(2) -0.0065(18) 0.0102(18) -0.0025(17) C3 0.019(2) 0.032(2) 0.032(2) -0.0046(18) 0.0107(17) -0.0018(17) C4 0.028(2) 0.035(2) 0.030(2) -0.0004(18) 0.0102(18) -0.0003(18) C5 0.022(2) 0.028(2) 0.035(2) -0.0032(18) 0.0083(18) -0.0015(17) C6 0.023(2) 0.031(2) 0.032(2) -0.0060(17) 0.0109(17) -0.0005(17) C7 0.024(2) 0.033(2) 0.033(2) -0.0046(18) 0.0071(19) -0.0033(18) C8 0.038(3) 0.040(3) 0.032(3) 0.004(2) 0.004(2) -0.005(2) C9 0.030(2) 0.023(2) 0.032(2) -0.0030(17) 0.0105(19) 0.0019(17) C10 0.034(2) 0.068(3) 0.023(2) -0.004(2) 0.0105(19) 0.010(2) C11 0.047(3) 0.033(2) 0.036(2) -0.0028(19) 0.015(2) -0.002(2) C12 0.097(4) 0.027(2) 0.077(4) -0.011(2) 0.041(3) 0.009(3) C13 0.029(2) 0.032(2) 0.026(2) 0.0016(17) 0.0074(18) -0.0022(18) C14 0.023(2) 0.034(2) 0.026(2) -0.0007(17) 0.0086(17) -0.0036(17) C15 0.033(2) 0.022(2) 0.025(2) -0.0010(16) 0.0092(18) -0.0095(17) C16 0.027(2) 0.031(2) 0.029(2) -0.0010(18) 0.0126(18) -0.0035(18) C17 0.034(2) 0.038(2) 0.025(2) -0.0032(18) 0.0163(18) -0.0063(19) C18 0.027(2) 0.036(2) 0.028(2) -0.0050(18) 0.0071(18) -0.0057(18) C19 0.033(2) 0.028(2) 0.039(2) 0.0016(18) 0.016(2) -0.0078(18) C20 0.020(2) 0.027(2) 0.026(2) 0.0013(17) 0.0032(17) 0.0053(17) C21 0.0214(19) 0.030(2) 0.023(2) -0.0059(17) 0.0059(16) 0.0025(17) C22 0.024(2) 0.026(2) 0.023(2) -0.0025(16) 0.0076(17) -0.0011(16) C23 0.0202(19) 0.022(2) 0.026(2) 0.0013(16) 0.0029(16) 0.0058(16) C24 0.0154(18) 0.030(2) 0.023(2) -0.0031(16) 0.0033(16) -0.0009(16) C25 0.0213(19) 0.0208(19) 0.022(2) -0.0029(15) 0.0007(16) -0.0020(16) C26 0.023(2) 0.026(2) 0.026(2) -0.0049(16) 0.0056(17) 0.0089(17) C27 0.033(2) 0.043(3) 0.032(2) 0.0061(19) 0.0044(19) 0.013(2) C28 0.038(2) 0.045(3) 0.037(3) 0.006(2) 0.016(2) 0.022(2) C29 0.043(3) 0.027(2) 0.038(3) -0.0005(19) 0.015(2) 0.012(2) C30 0.046(3) 0.041(3) 0.031(2) -0.0044(19) 0.013(2) 0.018(2) C31 0.046(3) 0.039(2) 0.036(3) 0.000(2) 0.019(2) 0.021(2) C32 0.041(3) 0.034(2) 0.039(3) -0.0045(19) 0.019(2) 0.012(2) C33 0.047(3) 0.030(2) 0.037(3) 0.0004(19) 0.018(2) 0.015(2) C34 0.054(3) 0.025(2) 0.033(2) 0.0008(18) 0.019(2) 0.017(2) C35 0.100(5) 0.083(4) 0.057(3) 0.004(3) 0.048(3) 0.054(4) C36 0.031(2) 0.046(3) 0.030(2) -0.012(2) 0.0120(19) -0.009(2) N7 0.050(3) 0.137(5) 0.045(3) -0.022(3) 0.017(2) -0.011(3) C37 0.035(3) 0.068(3) 0.032(3) -0.002(2) 0.016(2) 0.001(2) C38 0.051(3) 0.047(3) 0.039(3) 0.005(2) 0.015(2) -0.009(2) N8 0.116(5) 0.072(4) 0.133(5) -0.042(3) 0.073(4) -0.039(3) C39 0.070(4) 0.062(4) 0.050(3) -0.005(3) 0.017(3) -0.035(3) C40 0.045(3) 0.067(4) 0.060(3) 0.015(3) -0.002(3) 0.001(3) N9 0.063(3) 0.113(4) 0.086(4) -0.055(3) -0.011(3) 0.028(3) C41 0.046(3) 0.052(3) 0.076(4) -0.030(3) 0.012(3) -0.004(3) C42 0.066(4) 0.042(3) 0.145(6) -0.001(3) 0.045(4) -0.004(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 O1 C7 1.240(4) . ? O2 C9 1.237(4) . ? O3 C11 1.230(5) . ? O4 C20 1.234(4) . ? O5 C28 1.229(5) . ? O6 C36 1.227(5) . ? N1 C7 1.365(5) . ? N1 C13 1.436(5) . ? N1 C8 1.466(5) . ? N2 C9 1.339(5) . ? N2 C21 1.445(4) . ? N2 C10 1.464(5) . ? N3 C11 1.349(5) . ? N3 C29 1.435(5) . ? N3 C12 1.459(5) . ? N4 C20 1.366(5) . ? N4 C15 1.442(5) . ? N4 C19 1.476(4) . ? N5 C28 1.355(5) . ? N5 C23 1.433(4) . ? N5 C27 1.465(5) . ? N6 C36 1.343(5) . ? N6 C31 1.449(5) . ? N6 C35 1.466(5) . ? C1 C6 1.384(5) . ? C1 C2 1.398(5) . ? C1 C7 1.492(5) . ? C2 C3 1.383(5) . ? C2 H2 0.9500 . ? C3 C4 1.384(5) . ? C3 C9 1.500(5) . ? C4 C5 1.392(5) . ? C4 H4 0.9500 . ? C5 C6 1.398(5) . ? C5 C11 1.487(5) . ? C6 H6 0.9500 . ? C8 H8A 1.09(4) . ? C8 H8B 0.99(4) . ? C8 H8C 0.90(6) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.377(5) . ? C13 C14 1.388(5) . ? C14 C15 1.390(5) . ? C14 H14 0.9500 . ? C15 C16 1.375(5) . ? C16 C17 1.391(5) . ? C16 H16 0.9500 . ? C17 C18 1.395(5) . ? C17 C36 1.496(5) . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.481(5) . ? C21 C26 1.381(5) . ? C21 C22 1.386(5) . ? C22 C23 1.388(5) . ? C22 H22 0.9500 . ? C23 C24 1.391(5) . ? C24 C25 1.393(5) . ? C24 H24 0.9500 . ? C25 C26 1.391(5) . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C33 1.493(6) . ? C29 C34 1.391(6) . ? C29 C30 1.392(6) . ? C30 C31 1.381(6) . ? C30 H30 0.9500 . ? C31 C32 1.372(6) . ? C32 C33 1.379(5) . ? C32 H32 0.9500 . ? C33 C34 1.392(6) . ? C34 H34 0.9500 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? N7 C37 1.137(6) . ? C37 C38 1.450(6) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? N8 C39 1.154(7) . ? C39 C40 1.426(8) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? N9 C41 1.150(6) . ? C41 C42 1.404(7) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? 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 C7 N1 C13 121.3(3) . . ? C7 N1 C8 119.8(3) . . ? C13 N1 C8 115.2(3) . . ? C9 N2 C21 121.4(3) . . ? C9 N2 C10 120.5(3) . . ? C21 N2 C10 117.8(3) . . ? C11 N3 C29 124.4(3) . . ? C11 N3 C12 119.0(4) . . ? C29 N3 C12 116.4(4) . . ? C20 N4 C15 120.6(3) . . ? C20 N4 C19 119.8(3) . . ? C15 N4 C19 115.8(3) . . ? C28 N5 C23 122.2(3) . . ? C28 N5 C27 119.2(3) . . ? C23 N5 C27 115.7(3) . . ? C36 N6 C31 121.5(3) . . ? C36 N6 C35 120.4(4) . . ? C31 N6 C35 117.8(4) . . ? C6 C1 C2 119.9(4) . . ? C6 C1 C7 122.0(3) . . ? C2 C1 C7 117.7(3) . . ? C3 C2 C1 120.0(4) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 C9 121.8(3) . . ? C4 C3 C9 118.3(3) . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.4(4) . . ? C4 C5 C11 118.6(4) . . ? C6 C5 C11 121.5(3) . . ? C1 C6 C5 120.0(3) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? O1 C7 N1 122.1(4) . . ? O1 C7 C1 120.8(3) . . ? N1 C7 C1 117.1(3) . . ? N1 C8 H8A 110.5(19) . . ? N1 C8 H8B 112(2) . . ? H8A C8 H8B 103(3) . . ? N1 C8 H8C 116(4) . . ? H8A C8 H8C 106(4) . . ? H8B C8 H8C 109(4) . . ? O2 C9 N2 122.7(3) . . ? O2 C9 C3 121.3(3) . . ? N2 C9 C3 115.9(3) . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 N3 120.6(4) . . ? O3 C11 C5 119.7(4) . . ? N3 C11 C5 119.8(4) . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 120.4(4) . . ? C18 C13 N1 120.3(3) . . ? C14 C13 N1 119.0(3) . . ? C13 C14 C15 119.5(4) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.8(4) . . ? C16 C15 N4 120.0(3) . . ? C14 C15 N4 119.0(3) . . ? C15 C16 C17 119.4(4) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C18 120.3(4) . . ? C16 C17 C36 120.6(4) . . ? C18 C17 C36 119.0(4) . . ? C13 C18 C17 119.6(4) . . ? C13 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 N4 122.0(3) . . ? O4 C20 C25 120.8(3) . . ? N4 C20 C25 117.0(3) . . ? C26 C21 C22 121.2(3) . . ? C26 C21 N2 119.5(3) . . ? C22 C21 N2 119.2(3) . . ? C21 C22 C23 118.9(3) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? C22 C23 C24 120.4(3) . . ? C22 C23 N5 119.7(3) . . ? C24 C23 N5 119.7(3) . . ? C23 C24 C25 120.2(3) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 119.3(3) . . ? C26 C25 C20 121.1(3) . . ? C24 C25 C20 118.9(3) . . ? C21 C26 C25 119.9(3) . . ? C21 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? N5 C27 H27A 109.5 . . ? N5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O5 C28 N5 121.2(4) . . ? O5 C28 C33 120.9(4) . . ? N5 C28 C33 117.8(3) . . ? C34 C29 C30 119.4(4) . . ? C34 C29 N3 120.9(4) . . ? C30 C29 N3 119.4(4) . . ? C31 C30 C29 119.4(4) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C32 C31 C30 121.2(4) . . ? C32 C31 N6 119.8(4) . . ? C30 C31 N6 118.9(4) . . ? C31 C32 C33 119.8(4) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C32 C33 C34 119.8(4) . . ? C32 C33 C28 119.9(4) . . ? C34 C33 C28 120.0(4) . . ? C29 C34 C33 120.2(4) . . ? C29 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? N6 C35 H35A 109.5 . . ? N6 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N6 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O6 C36 N6 121.6(4) . . ? O6 C36 C17 121.8(4) . . ? N6 C36 C17 116.6(3) . . ? N7 C37 C38 178.8(6) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N8 C39 C40 178.4(7) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? N9 C41 C42 178.1(6) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.264 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.062