# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Jonathan L. Sessler' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Texas at Austin 1 University Station A5300 Austin TX 78712 UNITED STATES OF AMERICA ; _publ_contact_author_email SESSLER@MAIL.UTEXAS.EDU _publ_section_title ; Acyclic pyrrole-based anion receptors: Design, synthesis, and anion binding properties ; loop_ _publ_author_name J.L.Sessler N.M.Barkey V.Lynch G.D.Pantos data_3 _database_code_depnum_ccdc_archive 'CCDC 625744' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H29 N5 O10, C H2 Cl2' _chemical_formula_sum 'C28 H31 Cl2 N5 O10' _chemical_formula_weight 668.48 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6399(4) _cell_length_b 12.1551(4) _cell_length_c 12.5581(4) _cell_angle_alpha 75.915(2) _cell_angle_beta 72.576(2) _cell_angle_gamma 76.920(2) _cell_volume 1621.52(9) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6159 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27.5 _exptl_crystal_description laths _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10314 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5681 _reflns_number_gt 3283 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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. A columnar shaped region near 1/2, 0, z contained disordered solvent. The solvent appeared to be dichloromethane, which could not be modeled satisfactorily. The contribution to the scattering was removed by use of the utility, SQUEEZE (Sluis and Spek, 1990), in PLATON98 (Spek, 1998). PLATON98 was used as incorporated in WinGX (Farrugia, 1999). One of the ethyl groups was found to be disordered about two principal orientations. The disorder was modeled by restraining the C-C bond lengths of the two orientations to be equivalent. The site occupancy factor of one component composed of atoms C26 and C27 was assigned the variable x. The site occupancy of the atoms of the alternate confor- mation was assigned to (1-x). A common isotropic displacement parameter was refined for the atom pairs, C26 and C26a, and C27 and C27a, while the site occupancy factor x was refined. The site occupancy factor for C26 and C27 refined to 80(2)%. C26 and C27 were refined anisotropically while C26a and C27a were refined isotropically. ; _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^)+(0.1040P)^2^+0.0585P] 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 0.022(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5681 _refine_ls_number_parameters 388 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1227 _refine_ls_R_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.2147 _refine_ls_wR_factor_gt 0.1973 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.048 _refine_ls_shift/su_mean 0.004 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 -0.2338(2) 0.3910(2) 0.57990(19) 0.0515(7) Uani 1 1 d . . . O2 O -0.2437(2) 0.6061(2) 0.01119(18) 0.0450(6) Uani 1 1 d . . . O3 O 0.4117(2) 0.2756(3) 0.5158(2) 0.0696(9) Uani 1 1 d . . . O4 O 0.3117(2) 0.2111(2) 0.69382(19) 0.0535(7) Uani 1 1 d . . . O5 O 0.1530(2) 0.3530(2) 0.27242(18) 0.0518(7) Uani 1 1 d . . . O6 O 0.3303(2) 0.2951(2) 0.32018(19) 0.0511(7) Uani 1 1 d . . . O7 O 0.1159(2) 0.6192(2) 0.15577(19) 0.0520(7) Uani 1 1 d . A . O8 O 0.2877(2) 0.6488(3) 0.0193(2) 0.0588(8) Uani 1 1 d . A . O9 O 0.3068(2) 0.8355(3) -0.1607(2) 0.0681(9) Uani 1 1 d . . . O10 O 0.2507(2) 0.8422(3) -0.3177(2) 0.0719(9) Uani 1 1 d D . . N1 N -0.0069(2) 0.3425(3) 0.6165(2) 0.0408(7) Uani 1 1 d . . . H1N H -0.0838 0.3562 0.6596 0.049 Uiso 1 1 d R . . N2 N -0.0584(2) 0.3950(2) 0.4367(2) 0.0395(7) Uani 1 1 d . . . H2N H -0.0286 0.4122 0.3609 0.047 Uiso 1 1 d R . . N3 N -0.1928(2) 0.4900(2) 0.2851(2) 0.0350(7) Uani 1 1 d . . . N4 N -0.0798(2) 0.5987(2) 0.0777(2) 0.0368(7) Uani 1 1 d . . . H4N H -0.0484 0.5728 0.1383 0.044 Uiso 1 1 d R . . N5 N -0.0414(2) 0.6931(2) -0.1185(2) 0.0377(7) Uani 1 1 d . . . H5N H -0.1104 0.6830 -0.1306 0.045 Uiso 1 1 d R . . C1 C 0.0941(3) 0.3024(3) 0.6554(3) 0.0379(8) Uani 1 1 d . . . H1 H 0.0951 0.2835 0.7340 0.045 Uiso 1 1 d R . . C2 C 0.1935(3) 0.2929(3) 0.5666(3) 0.0361(8) Uani 1 1 d . . . C3 C 0.1514(3) 0.3280(3) 0.4648(3) 0.0360(8) Uani 1 1 d . . . C4 C 0.0265(3) 0.3579(3) 0.5012(3) 0.0365(8) Uani 1 1 d . . . C5 C -0.1830(3) 0.4082(3) 0.4782(3) 0.0394(8) Uani 1 1 d . . . C6 C -0.2502(3) 0.4412(3) 0.3888(3) 0.0374(8) Uani 1 1 d . . . C7 C -0.3684(3) 0.4195(3) 0.4158(3) 0.0456(9) Uani 1 1 d . . . H7 H -0.4070 0.3871 0.4926 0.055 Uiso 1 1 d R . . C8 C -0.4298(3) 0.4451(4) 0.3325(3) 0.0536(10) Uani 1 1 d . . . H8 H -0.5106 0.4284 0.3480 0.064 Uiso 1 1 d R . . C9 C -0.3714(3) 0.4970(3) 0.2237(3) 0.0466(9) Uani 1 1 d . . . H9 H -0.4104 0.5185 0.1626 0.056 Uiso 1 1 d R . . C10 C -0.2541(3) 0.5182(3) 0.2044(3) 0.0351(8) Uani 1 1 d . . . C11 C -0.1929(3) 0.5770(3) 0.0890(3) 0.0362(8) Uani 1 1 d . . . C12 C -0.0090(3) 0.6576(3) -0.0190(3) 0.0348(8) Uani 1 1 d . . . C13 C 0.1041(3) 0.6868(3) -0.0342(3) 0.0360(8) Uani 1 1 d . A . C14 C 0.1391(3) 0.7468(3) -0.1504(3) 0.0388(8) Uani 1 1 d . . . C15 C 0.0475(3) 0.7473(3) -0.1977(3) 0.0427(9) Uani 1 1 d . A . H15 H 0.0461 0.7812 -0.2749 0.051 Uiso 1 1 d R . . C16 C 0.3170(3) 0.2598(3) 0.5841(3) 0.0431(9) Uani 1 1 d . . . C17 C 0.4264(3) 0.1780(4) 0.7251(3) 0.0583(11) Uani 1 1 d . . . H17A H 0.4629 0.2443 0.7154 0.070 Uiso 1 1 d R . . H17B H 0.4820 0.1261 0.6790 0.070 Uiso 1 1 d R . . C18 C 0.3978(4) 0.1210(4) 0.8490(3) 0.0680(12) Uani 1 1 d . . . H18A H 0.4707 0.0965 0.8751 0.102 Uiso 1 1 d R . . H18B H 0.3417 0.1741 0.8935 0.102 Uiso 1 1 d R . . H18C H 0.3608 0.0554 0.8569 0.102 Uiso 1 1 d R . . C19 C 0.2103(3) 0.3271(3) 0.3449(3) 0.0400(9) Uani 1 1 d . . . C20 C 0.3922(3) 0.2868(4) 0.2023(3) 0.0584(11) Uani 1 1 d . . . H20A H 0.4747 0.3000 0.1839 0.070 Uiso 1 1 d R . . H20B H 0.3500 0.3443 0.1535 0.070 Uiso 1 1 d R . . C21 C 0.3909(4) 0.1742(5) 0.1804(4) 0.0855(16) Uani 1 1 d . . . H21A H 0.4304 0.1689 0.1025 0.128 Uiso 1 1 d R . . H21B H 0.4339 0.1170 0.2288 0.128 Uiso 1 1 d R . . H21C H 0.3082 0.1617 0.1982 0.128 Uiso 1 1 d R . . C22 C 0.1676(3) 0.6508(3) 0.0566(3) 0.0430(9) Uani 1 1 d . . . C23 C 0.3548(4) 0.6166(5) 0.1043(4) 0.0756(14) Uani 1 1 d . . . H23A H 0.4373 0.5834 0.0720 0.091 Uiso 1 1 d R A . H23B H 0.3189 0.5613 0.1671 0.091 Uiso 1 1 d R . . C24 C 0.3549(5) 0.7176(6) 0.1445(5) 0.1041(19) Uani 1 1 d . A . H24A H 0.4003 0.6991 0.2008 0.156 Uiso 1 1 d R . . H24B H 0.3914 0.7723 0.0813 0.156 Uiso 1 1 d R . . H24C H 0.2721 0.7500 0.1770 0.156 Uiso 1 1 d R . . C25 C 0.2425(3) 0.8096(3) -0.2055(3) 0.0488(10) Uani 1 1 d . A . C26 C 0.3483(5) 0.9127(7) -0.3773(4) 0.0692(17) Uani 0.80 1 d PD A 1 H26A H 0.4291 0.8685 -0.3875 0.083 Uiso 0.80 1 d PR A 1 H26B H 0.3415 0.9700 -0.3339 0.083 Uiso 0.80 1 d PR A 1 C27 C 0.3204(5) 0.9767(6) -0.4874(6) 0.0853(19) Uani 0.80 1 d PD A 1 H27A H 0.3780 1.0271 -0.5298 0.128 Uiso 0.80 1 d PR A 1 H27B H 0.3271 0.9181 -0.5292 0.128 Uiso 0.80 1 d PR A 1 H27C H 0.2392 1.0200 -0.4755 0.128 Uiso 0.80 1 d PR A 1 C26A C 0.353(2) 0.8556(18) -0.4217(18) 0.098(10) Uiso 0.20 1 d PD A 2 H26C H 0.3639 0.8220 -0.4865 0.117 Uiso 0.20 1 d PR A 2 H26D H 0.4253 0.8351 -0.3946 0.117 Uiso 0.20 1 d PR A 2 C27A C 0.325(2) 0.9773(19) -0.403(2) 0.050(6) Uiso 0.20 1 d PD A 2 H27D H 0.3838 1.0173 -0.4620 0.075 Uiso 0.20 1 d PR A 2 H27E H 0.2500 0.9912 -0.4248 0.075 Uiso 0.20 1 d PR A 2 H27F H 0.3108 1.0043 -0.3338 0.075 Uiso 0.20 1 d PR A 2 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 0.0400(14) 0.081(2) 0.0305(15) -0.0035(12) -0.0064(11) -0.0153(12) O2 0.0421(14) 0.0591(17) 0.0378(14) -0.0022(11) -0.0199(11) -0.0108(11) O3 0.0426(16) 0.116(3) 0.0500(17) 0.0049(16) -0.0191(14) -0.0246(16) O4 0.0485(15) 0.0757(19) 0.0390(15) -0.0074(13) -0.0233(12) -0.0028(13) O5 0.0385(14) 0.087(2) 0.0316(13) -0.0103(12) -0.0149(11) -0.0060(12) O6 0.0344(14) 0.082(2) 0.0370(14) -0.0148(12) -0.0120(11) -0.0017(12) O7 0.0470(15) 0.080(2) 0.0300(14) -0.0099(12) -0.0108(12) -0.0121(13) O8 0.0367(15) 0.099(2) 0.0437(15) -0.0032(14) -0.0177(12) -0.0172(14) O9 0.0509(17) 0.085(2) 0.0720(19) 0.0080(16) -0.0265(15) -0.0282(15) O10 0.0571(17) 0.099(2) 0.0464(17) 0.0052(15) 0.0009(13) -0.0254(16) N1 0.0383(16) 0.059(2) 0.0262(15) -0.0055(13) -0.0090(12) -0.0119(14) N2 0.0335(16) 0.059(2) 0.0263(14) -0.0033(13) -0.0095(12) -0.0108(13) N3 0.0311(14) 0.0447(18) 0.0308(16) -0.0075(13) -0.0089(12) -0.0082(12) N4 0.0344(15) 0.0498(19) 0.0287(15) -0.0063(13) -0.0132(12) -0.0064(13) N5 0.0353(15) 0.0454(18) 0.0321(15) -0.0032(13) -0.0129(12) -0.0046(13) C1 0.039(2) 0.048(2) 0.0310(18) -0.0049(15) -0.0185(16) -0.0077(16) C2 0.0353(19) 0.046(2) 0.0323(19) -0.0031(15) -0.0156(16) -0.0115(15) C3 0.0299(18) 0.049(2) 0.0319(18) -0.0072(15) -0.0098(14) -0.0105(15) C4 0.0369(19) 0.047(2) 0.0290(18) -0.0061(15) -0.0125(15) -0.0096(15) C5 0.0326(19) 0.055(2) 0.031(2) -0.0053(16) -0.0047(15) -0.0142(16) C6 0.0326(18) 0.046(2) 0.0316(19) -0.0052(15) -0.0072(15) -0.0068(15) C7 0.035(2) 0.063(3) 0.038(2) -0.0048(17) -0.0082(16) -0.0137(17) C8 0.035(2) 0.079(3) 0.050(2) -0.005(2) -0.0144(18) -0.0177(19) C9 0.038(2) 0.063(3) 0.042(2) -0.0052(18) -0.0188(17) -0.0081(17) C10 0.0316(18) 0.042(2) 0.0356(19) -0.0122(15) -0.0127(15) -0.0037(15) C11 0.0354(19) 0.041(2) 0.0342(19) -0.0101(15) -0.0110(15) -0.0049(15) C12 0.0363(19) 0.041(2) 0.0271(18) -0.0100(15) -0.0078(15) -0.0031(15) C13 0.0370(19) 0.042(2) 0.0300(18) -0.0102(15) -0.0102(14) -0.0024(15) C14 0.0359(19) 0.045(2) 0.0325(19) -0.0084(15) -0.0069(15) -0.0019(16) C15 0.043(2) 0.050(2) 0.0324(19) -0.0058(16) -0.0109(16) -0.0027(17) C16 0.046(2) 0.051(2) 0.037(2) -0.0073(17) -0.0157(18) -0.0116(17) C17 0.055(2) 0.074(3) 0.056(2) -0.011(2) -0.037(2) -0.001(2) C18 0.075(3) 0.077(3) 0.058(3) -0.005(2) -0.042(2) -0.001(2) C19 0.0308(19) 0.057(2) 0.0331(19) -0.0061(16) -0.0099(16) -0.0097(16) C20 0.042(2) 0.092(3) 0.035(2) -0.017(2) -0.0058(17) 0.000(2) C21 0.081(3) 0.109(5) 0.062(3) -0.035(3) -0.019(2) 0.014(3) C22 0.040(2) 0.054(2) 0.038(2) -0.0119(17) -0.0107(17) -0.0105(17) C23 0.056(3) 0.114(4) 0.066(3) -0.009(3) -0.032(2) -0.019(3) C24 0.113(4) 0.135(6) 0.081(4) 0.001(4) -0.047(3) -0.046(4) C25 0.040(2) 0.055(3) 0.041(2) -0.0014(18) -0.0051(18) -0.0010(18) C26 0.051(3) 0.080(5) 0.057(4) 0.014(4) 0.004(3) -0.023(3) C27 0.072(4) 0.090(5) 0.075(4) 0.011(4) -0.003(3) -0.024(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 C5 1.224(4) . ? O2 C11 1.230(4) . ? O3 C16 1.198(4) . ? O4 C16 1.350(4) . ? O4 C17 1.447(4) . ? O5 C19 1.225(4) . ? O6 C19 1.323(4) . ? O6 C20 1.457(4) . ? O7 C22 1.218(4) . ? O8 C22 1.331(4) . ? O8 C23 1.436(4) . ? O9 C25 1.192(4) . ? O10 C25 1.348(4) . ? O10 C26A 1.484(11) . ? O10 C26 1.485(6) . ? N1 C1 1.352(4) . ? N1 C4 1.359(4) . ? N1 H1N 0.9000 . ? N2 C5 1.373(4) . ? N2 C4 1.390(4) . ? N2 H2N 0.9001 . ? N3 C6 1.334(4) . ? N3 C10 1.344(4) . ? N4 C11 1.360(4) . ? N4 C12 1.383(4) . ? N4 H4N 0.8999 . ? N5 C12 1.354(4) . ? N5 C15 1.367(4) . ? N5 H5N 0.9000 . ? C1 C2 1.351(4) . ? C1 H1 0.9599 . ? C2 C3 1.439(4) . ? C2 C16 1.470(5) . ? C3 C4 1.378(4) . ? C3 C19 1.457(4) . ? C5 C6 1.483(5) . ? C6 C7 1.386(5) . ? C7 C8 1.376(5) . ? C7 H7 0.9600 . ? C8 C9 1.395(5) . ? C8 H8 0.9600 . ? C9 C10 1.385(5) . ? C9 H9 0.9600 . ? C10 C11 1.492(5) . ? C12 C13 1.387(5) . ? C13 C14 1.445(4) . ? C13 C22 1.467(5) . ? C14 C15 1.365(5) . ? C14 C25 1.473(5) . ? C15 H15 0.9600 . ? C17 C18 1.510(5) . ? C17 H17A 0.9601 . ? C17 H17B 0.9600 . ? C18 H18A 0.9599 . ? C18 H18B 0.9600 . ? C18 H18C 0.9601 . ? C20 C21 1.463(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9599 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9599 . ? C23 C24 1.437(7) . ? C23 H23A 0.9599 . ? C23 H23B 0.9600 . ? C24 H24A 0.9601 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C26 C27 1.502(7) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C26A C27A 1.501(12) . ? C26A H26C 0.9601 . ? C26A H26D 0.9600 . ? C27A H27D 0.9601 . ? C27A H27E 0.9600 . ? C27A H27F 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 C16 O4 C17 116.6(3) . . ? C19 O6 C20 116.9(3) . . ? C22 O8 C23 116.4(3) . . ? C25 O10 C26A 134.7(13) . . ? C25 O10 C26 112.2(3) . . ? C1 N1 C4 108.9(3) . . ? C1 N1 H1N 125.8 . . ? C4 N1 H1N 125.3 . . ? C5 N2 C4 126.0(3) . . ? C5 N2 H2N 117.2 . . ? C4 N2 H2N 116.8 . . ? C6 N3 C10 117.3(3) . . ? C11 N4 C12 125.5(3) . . ? C11 N4 H4N 117.4 . . ? C12 N4 H4N 117.2 . . ? C12 N5 C15 109.0(3) . . ? C12 N5 H5N 125.7 . . ? C15 N5 H5N 125.3 . . ? C2 C1 N1 109.4(3) . . ? C2 C1 H1 125.2 . . ? N1 C1 H1 125.3 . . ? C1 C2 C3 107.2(3) . . ? C1 C2 C16 120.9(3) . . ? C3 C2 C16 131.8(3) . . ? C4 C3 C2 105.4(3) . . ? C4 C3 C19 120.4(3) . . ? C2 C3 C19 133.9(3) . . ? N1 C4 C3 109.1(3) . . ? N1 C4 N2 122.3(3) . . ? C3 C4 N2 128.6(3) . . ? O1 C5 N2 122.9(3) . . ? O1 C5 C6 123.1(3) . . ? N2 C5 C6 114.0(3) . . ? N3 C6 C7 123.0(3) . . ? N3 C6 C5 117.9(3) . . ? C7 C6 C5 119.1(3) . . ? C8 C7 C6 119.7(3) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 118.0(3) . . ? C7 C8 H8 121.5 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 118.7(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 121.7 . . ? N3 C10 C9 123.3(3) . . ? N3 C10 C11 118.0(3) . . ? C9 C10 C11 118.7(3) . . ? O2 C11 N4 123.0(3) . . ? O2 C11 C10 121.6(3) . . ? N4 C11 C10 115.3(3) . . ? N5 C12 N4 122.9(3) . . ? N5 C12 C13 108.8(3) . . ? N4 C12 C13 128.2(3) . . ? C12 C13 C14 106.3(3) . . ? C12 C13 C22 121.3(3) . . ? C14 C13 C22 132.3(3) . . ? C15 C14 C13 106.2(3) . . ? C15 C14 C25 125.0(3) . . ? C13 C14 C25 128.4(3) . . ? C14 C15 N5 109.7(3) . . ? C14 C15 H15 124.8 . . ? N5 C15 H15 125.5 . . ? O3 C16 O4 121.9(3) . . ? O3 C16 C2 127.8(3) . . ? O4 C16 C2 110.3(3) . . ? O4 C17 C18 106.8(3) . . ? O4 C17 H17A 110.7 . . ? C18 C17 H17A 109.4 . . ? O4 C17 H17B 110.3 . . ? C18 C17 H17B 110.8 . . ? H17A C17 H17B 108.9 . . ? C17 C18 H18A 110.9 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 108.0 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 O6 122.4(3) . . ? O5 C19 C3 122.5(3) . . ? O6 C19 C3 115.1(3) . . ? O6 C20 C21 110.8(4) . . ? O6 C20 H20A 110.7 . . ? C21 C20 H20A 110.0 . . ? O6 C20 H20B 109.1 . . ? C21 C20 H20B 107.9 . . ? H20A C20 H20B 108.2 . . ? C20 C21 H21A 111.1 . . ? C20 C21 H21B 107.6 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.7 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O7 C22 O8 123.3(3) . . ? O7 C22 C13 122.9(3) . . ? O8 C22 C13 113.7(3) . . ? O8 C23 C24 108.9(4) . . ? O8 C23 H23A 109.8 . . ? C24 C23 H23A 109.4 . . ? O8 C23 H23B 111.1 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 108.4 . . ? C23 C24 H24A 110.9 . . ? C23 C24 H24B 108.7 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 108.8 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O9 C25 O10 123.0(3) . . ? O9 C25 C14 127.4(3) . . ? O10 C25 C14 109.4(3) . . ? O10 C26 C27 106.7(4) . . ? O10 C26 H26A 113.3 . . ? C27 C26 H26A 112.9 . . ? O10 C26 H26B 108.6 . . ? C27 C26 H26B 106.2 . . ? H26A C26 H26B 108.8 . . ? C27 C26 H26D 109.1 . . ? H26D C26 H27D 109.0 . . ? C26 C27 H27A 111.8 . . ? C26 C27 H27B 104.9 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 111.6 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O10 C26A C27A 81.9(14) . . ? O10 C26A H26A 102.4 . . ? O10 C26A H26D 104.9 . . ? H26C C26A H26D 110.9 . . ? C26A C27A H26B 103.3 . . ? C26A C27A H27D 106.1 . . ? H26B C27A H27D 109.4 . . ? H27D C27A H27E 109.5 . . ? H27D C27A H27F 109.5 . . ? H27E C27A H27F 109.5 . . ? 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 C4 N1 C1 C2 0.9(4) . . . . ? N1 C1 C2 C3 -0.9(4) . . . . ? N1 C1 C2 C16 175.1(3) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C16 C2 C3 C4 -174.8(4) . . . . ? C1 C2 C3 C19 -173.2(4) . . . . ? C16 C2 C3 C19 11.3(7) . . . . ? C1 N1 C4 C3 -0.4(4) . . . . ? C1 N1 C4 N2 177.8(3) . . . . ? C2 C3 C4 N1 -0.2(4) . . . . ? C19 C3 C4 N1 174.7(3) . . . . ? C2 C3 C4 N2 -178.3(3) . . . . ? C19 C3 C4 N2 -3.4(6) . . . . ? C5 N2 C4 N1 -7.7(5) . . . . ? C5 N2 C4 C3 170.2(3) . . . . ? C4 N2 C5 O1 2.2(6) . . . . ? C4 N2 C5 C6 -175.8(3) . . . . ? C10 N3 C6 C7 -0.3(5) . . . . ? C10 N3 C6 C5 179.2(3) . . . . ? O1 C5 C6 N3 160.7(3) . . . . ? N2 C5 C6 N3 -21.3(5) . . . . ? O1 C5 C6 C7 -19.8(5) . . . . ? N2 C5 C6 C7 158.2(3) . . . . ? N3 C6 C7 C8 2.3(6) . . . . ? C5 C6 C7 C8 -177.2(3) . . . . ? C6 C7 C8 C9 -2.6(6) . . . . ? C7 C8 C9 C10 1.2(6) . . . . ? C6 N3 C10 C9 -1.2(5) . . . . ? C6 N3 C10 C11 177.7(3) . . . . ? C8 C9 C10 N3 0.7(5) . . . . ? C8 C9 C10 C11 -178.1(3) . . . . ? C12 N4 C11 O2 1.8(5) . . . . ? C12 N4 C11 C10 -176.3(3) . . . . ? N3 C10 C11 O2 -179.4(3) . . . . ? C9 C10 C11 O2 -0.5(5) . . . . ? N3 C10 C11 N4 -1.3(4) . . . . ? C9 C10 C11 N4 177.6(3) . . . . ? C15 N5 C12 N4 -179.3(3) . . . . ? C15 N5 C12 C13 -1.4(4) . . . . ? C11 N4 C12 N5 -5.5(5) . . . . ? C11 N4 C12 C13 176.9(3) . . . . ? N5 C12 C13 C14 1.7(4) . . . . ? N4 C12 C13 C14 179.6(3) . . . . ? N5 C12 C13 C22 -174.8(3) . . . . ? N4 C12 C13 C22 3.0(5) . . . . ? C12 C13 C14 C15 -1.4(4) . . . . ? C22 C13 C14 C15 174.6(4) . . . . ? C12 C13 C14 C25 170.8(3) . . . . ? C22 C13 C14 C25 -13.1(6) . . . . ? C13 C14 C15 N5 0.6(4) . . . . ? C25 C14 C15 N5 -172.0(3) . . . . ? C12 N5 C15 C14 0.4(4) . . . . ? C17 O4 C16 O3 -0.3(5) . . . . ? C17 O4 C16 C2 -177.6(3) . . . . ? C1 C2 C16 O3 -159.5(4) . . . . ? C3 C2 C16 O3 15.5(6) . . . . ? C1 C2 C16 O4 17.6(5) . . . . ? C3 C2 C16 O4 -167.4(4) . . . . ? C16 O4 C17 C18 -177.3(3) . . . . ? C20 O6 C19 O5 -2.7(5) . . . . ? C20 O6 C19 C3 176.7(3) . . . . ? C4 C3 C19 O5 0.5(5) . . . . ? C2 C3 C19 O5 173.6(4) . . . . ? C4 C3 C19 O6 -178.9(3) . . . . ? C2 C3 C19 O6 -5.7(6) . . . . ? C19 O6 C20 C21 -85.4(4) . . . . ? C23 O8 C22 O7 -5.5(5) . . . . ? C23 O8 C22 C13 178.7(3) . . . . ? C12 C13 C22 O7 -18.2(5) . . . . ? C14 C13 C22 O7 166.3(4) . . . . ? C12 C13 C22 O8 157.7(3) . . . . ? C14 C13 C22 O8 -17.8(5) . . . . ? C22 O8 C23 C24 -87.1(5) . . . . ? C26A O10 C25 O9 38.2(14) . . . . ? C26 O10 C25 O9 0.2(6) . . . . ? C26A O10 C25 C14 -145.8(13) . . . . ? C26 O10 C25 C14 176.2(5) . . . . ? C15 C14 C25 O9 160.1(4) . . . . ? C13 C14 C25 O9 -10.9(6) . . . . ? C15 C14 C25 O10 -15.8(5) . . . . ? C13 C14 C25 O10 173.3(3) . . . . ? C25 O10 C26 C27 -160.5(5) . . . . ? C26A O10 C26 C27 64.3(18) . . . . ? C25 O10 C26A C27A -93.6(16) . . . . ? C26 O10 C26A C27A -26.9(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.90 2.18 2.725(3) 118.7 . N2 H2N O5 0.90 2.12 2.734(3) 124.3 . N4 H4N O7 0.90 2.20 2.816(3) 125.5 . N5 H5N O2 0.90 2.15 2.702(3) 118.5 . N1 H1N O7 0.90 2.32 2.866(3) 119.2 2_566 N5 H5N O5 0.90 2.15 2.846(3) 133.7 2_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.352 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.077