# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_New_Global_Publ_Block _journal_name_full Org.Biomol.Chem. #TrackingRef 'MTPh2-deposit_ccdc759763.cif' _journal_coden_Cambridge 0177 # Added by publCIF - use a unique identifier for each data block #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Diego Savoia' # Name of author for correspondence _publ_contact_author_address # Address of author for correspondence ; Dipartimento di Chimica "G. Ciamician" Universit\`a di Bologna Via Selmi 2 40126 Bologna Italy ; _publ_contact_author_email diego.savoia@unibo.it _publ_contact_author_fax '+39 051 2099571' _publ_contact_author_phone ? _publ_requested_category ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Stereoselective synthesis of ring C-hexasubstituted trianglamines ; loop_ _publ_author_name _publ_author_address _publ_author_footnote D.Savoia ; Dipartimento di Chimica "G. Ciamician" Universit\`a di Bologna Via Selmi 2 40126 Bologna Italy ; ; ? ; A.Gualandi ; Dipartimento di Chimica "G. Ciamician" Universit\`a di Bologna Via Selmi 2 40126 Bologna Italy ; . H.Stoeckli-Evans ; Institute of Physics University of Neuch\^atel rue Emile-Argand 11 CH-2009 Neuch\^atel Switzerland ; . #============================================================================== data_MTPh2 _database_code_depnum_ccdc_archive 'CCDC 759763' #TrackingRef 'MTPh2-deposit_ccdc759763.cif' _audit_update_record ; 2009-12-27 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C78 H84 N6, 4(C2 H3 N)' _chemical_formula_sum 'C86 H96 N10' _chemical_formula_weight 1269.73 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R 3' _symmetry_space_group_name_Hall 'R 3' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -y,x-y,z 3 -x+y,-x,z 4 1/3+x,2/3+y,2/3+z 5 1/3-y,2/3+x-y,2/3+z 6 1/3-x+y,2/3-x,2/3+z 7 2/3+x,1/3+y,1/3+z 8 2/3-y,1/3+x-y,1/3+z 9 2/3-x+y,1/3-x,1/3+z _cell_length_a 23.3363(9) _cell_length_b 23.3363(9) _cell_length_c 12.2187(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5762.6(4) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15437 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 29.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2046 _exptl_absorpt_coefficient_mu 0.065 _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 173(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 'STOE IPDS-2' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18730 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 29.16 _reflns_number_total 3459 _reflns_number_gt 3113 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area V1.51 (Stoe & Cie, 2009)' _computing_cell_refinement 'X-Area V1.51' _computing_data_reduction 'X-RED32 V1.48 (Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'MERCURY (Macrea et al., 2006)' _computing_publication_material 'SHELXL-97 and PLATON (Spek, 2009)' _refine_special_details ; In the final cycles of refinement, in the absence of significant anomalous scattering effects, Friedel pairs were merged and \Df " set to zero. The NH H-atoms were located from difference electron-density maps and were refined with distance restraints of 0.88(2) \%A with U~iso~(H) = 1.2U~eq~(N). The C-bound H-atoms were included in calculated positions and treated as riding: C-H = 0.95 - 1.0 \%A, with U~iso~(H) = k \\times U~eq~(C), where k = 1.2 for CH and CH~2~ H-atoms and 1.5 for CH~3~ H-atoms. ; _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^+0.3878P] 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_abs_structure_details 'none; Friedel Pairs merged' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3459 _refine_ls_number_parameters 301 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1206 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags N1 N Uani 0.70140(8) 0.12825(9) 0.80842(14) 1.000 0.0263(5) . . N2 N Uani 0.82563(9) 0.24336(8) 0.82584(15) 1.000 0.0277(5) . . C1 C Uani 0.76131(10) 0.12807(10) 0.77126(15) 1.000 0.0239(5) . . C2 C Uani 0.81992(10) 0.17782(10) 0.84109(15) 1.000 0.0238(5) . . C3 C Uani 0.87817(10) 0.29726(10) 0.89027(17) 1.000 0.0278(5) . . C4 C Uani 0.88441(10) 0.36301(10) 0.85390(17) 1.000 0.0274(5) . . C5 C Uani 0.94670(11) 0.41749(11) 0.83586(18) 1.000 0.0301(6) . . C6 C Uani 0.82947(11) 0.37030(11) 0.8357(2) 1.000 0.0344(6) . . C7 C Uani 0.86446(11) 0.28350(10) 1.01209(18) 1.000 0.0305(6) . . C8 C Uani 0.80358(13) 0.26841(14) 1.0573(2) 1.000 0.0414(7) . . C9 C Uani 0.79149(18) 0.25466(16) 1.1685(2) 1.000 0.0536(10) . . C10 C Uani 0.83955(18) 0.25502(14) 1.2352(2) 1.000 0.0517(9) . . C11 C Uani 0.90010(17) 0.26954(14) 1.1916(2) 1.000 0.0494(9) . . C12 C Uani 0.91262(13) 0.28412(12) 1.0804(2) 1.000 0.0385(7) . . C13 C Uani 0.88284(11) 0.17614(11) 0.8117(2) 1.000 0.0320(6) . . C14 C Uani 0.87335(11) 0.10658(12) 0.8206(2) 1.000 0.0343(7) . . C15 C Uani 0.81532(12) 0.05738(11) 0.75111(19) 1.000 0.0336(6) . . C16 C Uani 0.75186(11) 0.05859(10) 0.77911(18) 1.000 0.0289(6) . . C17 C Uani 0.64190(10) 0.09088(10) 0.74156(15) 1.000 0.0247(5) . . C18 C Uani 0.58564(10) 0.10057(10) 0.78229(16) 1.000 0.0258(5) . . C19 C Uani 0.95420(11) 0.47796(11) 0.80110(18) 1.000 0.0290(5) . . C20 C Uani 0.83679(11) 0.43023(11) 0.8013(2) 1.000 0.0331(6) . . C21 C Uani 0.65227(10) 0.10522(11) 0.61852(17) 1.000 0.0266(5) . . C22 C Uani 0.69352(11) 0.16920(12) 0.57837(18) 1.000 0.0334(6) . . C23 C Uani 0.70314(12) 0.18051(13) 0.46609(19) 1.000 0.0375(7) . . C24 C Uani 0.67141(13) 0.12816(14) 0.39287(19) 1.000 0.0401(8) . . C25 C Uani 0.62971(14) 0.06494(14) 0.43230(19) 1.000 0.0404(8) . . C26 C Uani 0.62067(13) 0.05354(12) 0.54392(19) 1.000 0.0337(6) . . N3 N Uani 0.44470(16) 0.14380(17) 0.5761(3) 1.000 0.0657(11) . . C27 C Uani 0.48168(14) 0.14147(14) 0.5230(2) 1.000 0.0455(8) . . C28 C Uani 0.52909(19) 0.1369(2) 0.4498(4) 1.000 0.0770(15) . . N4 N Uani 0.66670 0.33330 0.8970(12) 0.500 0.055(3) . . C29 C Uani 0.66670 0.33330 0.9884(15) 0.500 0.055(4) . . C30 C Uani 0.66670 0.33330 1.1073(19) 0.500 0.100(6) . . N5 N Uani 0.66670 0.33330 0.4026(16) 0.500 0.114(6) . . C31 C Uani 0.66670 0.33330 0.4961(16) 0.500 0.073(4) . . C32 C Uani 0.66670 0.33330 0.6113(14) 0.500 0.088(5) . . H1 H Uiso 0.76990 0.14270 0.69310 1.000 0.0290 calc R H1N H Uiso 0.71060 0.16890 0.81900 1.000 0.0320 . R H2 H Uiso 0.80930 0.16490 0.91970 1.000 0.0290 calc R H2N H Uiso 0.83780 0.25490 0.75450 1.000 0.0330 . R H3 H Uiso 0.92090 0.29880 0.87340 1.000 0.0330 calc R H5 H Uiso 0.98490 0.41360 0.84730 1.000 0.0360 calc R H6 H Uiso 0.78630 0.33370 0.84710 1.000 0.0410 calc R H8 H Uiso 0.77010 0.26750 1.01190 1.000 0.0500 calc R H9 H Uiso 0.75010 0.24500 1.19870 1.000 0.0640 calc R H10 H Uiso 0.83100 0.24530 1.31090 1.000 0.0620 calc R H11 H Uiso 0.93310 0.26960 1.23730 1.000 0.0590 calc R H12 H Uiso 0.95440 0.29460 1.05100 1.000 0.0460 calc R H13A H Uiso 0.89610 0.19250 0.73590 1.000 0.0380 calc R H13B H Uiso 0.91910 0.20620 0.86130 1.000 0.0380 calc R H14A H Uiso 0.91420 0.10740 0.79620 1.000 0.0410 calc R H14B H Uiso 0.86540 0.09220 0.89800 1.000 0.0410 calc R H15A H Uiso 0.80800 0.01230 0.76350 1.000 0.0400 calc R H15B H Uiso 0.82600 0.06830 0.67270 1.000 0.0400 calc R H16A H Uiso 0.71620 0.02890 0.72830 1.000 0.0350 calc R H16B H Uiso 0.73780 0.04150 0.85430 1.000 0.0350 calc R H17 H Uiso 0.62730 0.04300 0.75140 1.000 0.0300 calc R H19 H Uiso 0.99730 0.51460 0.79020 1.000 0.0350 calc R H20 H Uiso 0.79860 0.43410 0.79040 1.000 0.0400 calc R H22 H Uiso 0.71510 0.20520 0.62800 1.000 0.0400 calc R H23 H Uiso 0.73140 0.22400 0.43950 1.000 0.0450 calc R H24 H Uiso 0.67830 0.13570 0.31640 1.000 0.0480 calc R H25 H Uiso 0.60720 0.02920 0.38250 1.000 0.0480 calc R H26 H Uiso 0.59250 0.00980 0.56990 1.000 0.0400 calc R H28A H Uiso 0.56360 0.13550 0.49350 1.000 0.1150 calc R H28B H Uiso 0.54940 0.17570 0.40160 1.000 0.1150 calc R H28C H Uiso 0.50600 0.09670 0.40560 1.000 0.1150 calc R H30A H Uiso 0.62760 0.33440 1.13400 0.170 0.1510 calc . H30B H Uiso 0.70680 0.37240 1.13400 0.170 0.1510 calc . H30C H Uiso 0.66560 0.29320 1.13400 0.170 0.1510 calc . H32A H Uiso 0.62940 0.29170 0.63800 0.170 0.1060 calc . H32B H Uiso 0.66230 0.37060 0.63800 0.170 0.1060 calc . H32C H Uiso 0.70830 0.33770 0.63800 0.170 0.1060 calc . 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 N1 0.0271(8) 0.0295(8) 0.0238(8) -0.0049(6) -0.0021(7) 0.0152(7) N2 0.0296(8) 0.0238(8) 0.0275(8) 0.0008(7) -0.0029(7) 0.0118(7) C1 0.0269(9) 0.0288(9) 0.0193(8) 0.0010(7) 0.0009(7) 0.0163(8) C2 0.0259(9) 0.0234(8) 0.0226(9) 0.0026(7) -0.0004(7) 0.0126(7) C3 0.0275(9) 0.0256(9) 0.0298(10) 0.0017(8) -0.0008(8) 0.0130(8) C4 0.0311(10) 0.0258(9) 0.0248(9) 0.0017(7) -0.0003(8) 0.0139(8) C5 0.0278(10) 0.0301(10) 0.0329(10) 0.0032(8) 0.0012(8) 0.0148(8) C6 0.0264(10) 0.0261(10) 0.0467(13) 0.0058(9) 0.0001(9) 0.0102(8) C7 0.0391(11) 0.0220(9) 0.0297(10) -0.0003(8) -0.0041(9) 0.0148(8) C8 0.0425(13) 0.0438(13) 0.0360(12) 0.0034(10) 0.0033(10) 0.0202(11) C9 0.0659(19) 0.0542(17) 0.0404(14) 0.0090(12) 0.0156(14) 0.0297(15) C10 0.080(2) 0.0413(14) 0.0305(12) 0.0038(10) 0.0025(12) 0.0279(14) C11 0.0693(19) 0.0454(14) 0.0366(13) -0.0001(11) -0.0131(13) 0.0309(14) C12 0.0449(13) 0.0347(11) 0.0379(12) 0.0006(9) -0.0069(10) 0.0215(10) C13 0.0289(10) 0.0316(10) 0.0369(11) 0.0038(8) 0.0023(8) 0.0162(8) C14 0.0333(11) 0.0366(11) 0.0404(12) 0.0050(9) 0.0023(9) 0.0231(9) C15 0.0433(12) 0.0323(10) 0.0342(11) -0.0005(9) 0.0014(9) 0.0257(9) C16 0.0319(10) 0.0276(9) 0.0275(10) -0.0024(8) -0.0036(8) 0.0151(8) C17 0.0281(9) 0.0247(9) 0.0235(9) -0.0024(7) -0.0005(7) 0.0148(8) C18 0.0290(9) 0.0295(9) 0.0218(9) -0.0005(7) 0.0000(7) 0.0167(8) C19 0.0270(9) 0.0272(9) 0.0311(10) 0.0047(8) 0.0035(8) 0.0122(8) C20 0.0253(10) 0.0276(10) 0.0444(12) 0.0040(9) -0.0010(9) 0.0117(8) C21 0.0274(9) 0.0337(10) 0.0246(9) -0.0016(7) -0.0011(7) 0.0198(8) C22 0.0321(10) 0.0389(11) 0.0286(10) 0.0034(9) -0.0005(8) 0.0172(9) C23 0.0338(11) 0.0485(13) 0.0314(11) 0.0090(10) 0.0023(9) 0.0215(10) C24 0.0449(13) 0.0629(16) 0.0250(10) 0.0031(10) -0.0014(9) 0.0363(13) C25 0.0567(14) 0.0516(14) 0.0272(11) -0.0111(10) -0.0093(10) 0.0379(13) C26 0.0459(12) 0.0353(11) 0.0294(10) -0.0041(9) -0.0046(9) 0.0274(10) N3 0.0693(18) 0.077(2) 0.0587(17) -0.0114(15) 0.0030(15) 0.0426(16) C27 0.0467(14) 0.0486(14) 0.0486(15) -0.0037(12) -0.0079(12) 0.0294(12) C28 0.0544(19) 0.091(3) 0.097(3) -0.006(2) 0.0145(19) 0.045(2) N4 0.026(2) 0.026(2) 0.112(9) 0.0000 0.0000 0.0132(12) C29 0.026(3) 0.026(3) 0.114(11) 0.0000 0.0000 0.0128(13) C30 0.094(7) 0.094(7) 0.113(15) 0.0000 0.0000 0.047(4) N5 0.125(9) 0.125(9) 0.094(12) 0.0000 0.0000 0.063(4) C31 0.060(5) 0.060(5) 0.100(11) 0.0000 0.0000 0.030(2) C32 0.095(7) 0.095(7) 0.074(10) 0.0000 0.0000 0.047(3) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.472(3) . . yes N1 C17 1.465(3) . . yes N2 C2 1.479(3) . . yes N2 C3 1.471(3) . . yes N1 H1N 0.8700 . . no N2 H2N 0.9100 . . no N3 C27 1.103(5) . . yes N4 C29 1.12(2) . . yes N5 C31 1.14(3) . . yes C1 C2 1.536(3) . . no C1 C16 1.526(3) . . no C2 C13 1.531(4) . . no C3 C4 1.533(3) . . no C3 C7 1.523(3) . . no C4 C5 1.389(3) . . no C4 C6 1.393(4) . . no C5 C19 1.398(3) . . no C6 C20 1.387(3) . . no C7 C8 1.396(4) . . no C7 C12 1.394(4) . . no C8 C9 1.392(4) . . no C9 C10 1.383(6) . . no C10 C11 1.384(6) . . no C11 C12 1.396(3) . . no C13 C14 1.529(3) . . no C14 C15 1.523(4) . . no C15 C16 1.534(4) . . no C17 C18 1.523(4) . . no C17 C21 1.533(3) . . no C18 C19 1.388(4) . 3_665 no C18 C20 1.399(3) . 3_665 no C21 C26 1.393(3) . . no C21 C22 1.400(3) . . no C22 C23 1.394(3) . . no C23 C24 1.392(4) . . no C24 C25 1.386(4) . . no C25 C26 1.385(3) . . no C1 H1 1.0000 . . no C2 H2 1.0000 . . no C3 H3 1.0000 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C8 H8 0.9500 . . no C9 H9 0.9500 . . no C10 H10 0.9500 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H13A 0.9900 . . no C13 H13B 0.9900 . . no C14 H14B 0.9900 . . no C14 H14A 0.9900 . . no C15 H15A 0.9900 . . no C15 H15B 0.9900 . . no C16 H16B 0.9900 . . no C16 H16A 0.9900 . . no C17 H17 1.0000 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C22 H22 0.9500 . . no C23 H23 0.9500 . . no C24 H24 0.9500 . . no C25 H25 0.9500 . . no C26 H26 0.9500 . . no C27 C28 1.467(6) . . no C28 H28B 0.9800 . . no C28 H28A 0.9800 . . no C28 H28C 0.9800 . . no C29 C30 1.45(3) . . no C31 C32 1.41(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C17 116.44(17) . . . yes C2 N2 C3 114.99(19) . . . yes C1 N1 H1N 109.00 . . . no C17 N1 H1N 112.00 . . . no C3 N2 H2N 105.00 . . . no C2 N2 H2N 106.00 . . . no N1 C1 C16 110.53(18) . . . yes C2 C1 C16 111.67(19) . . . no N1 C1 C2 108.34(17) . . . yes N2 C2 C1 107.30(18) . . . yes N2 C2 C13 113.90(18) . . . yes C1 C2 C13 110.69(18) . . . no N2 C3 C4 108.80(18) . . . yes C4 C3 C7 113.54(18) . . . no N2 C3 C7 110.21(17) . . . yes C3 C4 C5 119.6(2) . . . no C3 C4 C6 122.4(2) . . . no C5 C4 C6 118.0(2) . . . no C4 C5 C19 121.2(3) . . . no C4 C6 C20 121.0(2) . . . no C8 C7 C12 118.6(2) . . . no C3 C7 C12 120.0(2) . . . no C3 C7 C8 121.4(2) . . . no C7 C8 C9 120.5(3) . . . no C8 C9 C10 120.2(4) . . . no C9 C10 C11 120.0(3) . . . no C10 C11 C12 119.9(3) . . . no C7 C12 C11 120.7(3) . . . no C2 C13 C14 112.3(2) . . . no C13 C14 C15 111.3(2) . . . no C14 C15 C16 111.4(2) . . . no C1 C16 C15 112.18(19) . . . no N1 C17 C18 111.12(17) . . . yes N1 C17 C21 114.70(19) . . . yes C18 C17 C21 109.99(19) . . . no C19 C18 C20 117.8(3) 3_665 . 3_665 no C17 C18 C19 119.7(2) . . 3_665 no C17 C18 C20 122.5(2) . . 3_665 no C5 C19 C18 120.9(2) . . 2_655 no C6 C20 C18 121.2(3) . . 2_655 no C17 C21 C22 121.73(19) . . . no C17 C21 C26 119.70(19) . . . no C22 C21 C26 118.6(2) . . . no C21 C22 C23 120.4(2) . . . no C22 C23 C24 120.1(2) . . . no C23 C24 C25 119.6(2) . . . no C24 C25 C26 120.3(2) . . . no C21 C26 C25 120.9(2) . . . no N1 C1 H1 109.00 . . . no C2 C1 H1 109.00 . . . no C16 C1 H1 109.00 . . . no N2 C2 H2 108.00 . . . no C1 C2 H2 108.00 . . . no C13 C2 H2 108.00 . . . no N2 C3 H3 108.00 . . . no C4 C3 H3 108.00 . . . no C7 C3 H3 108.00 . . . no C4 C5 H5 119.00 . . . no C19 C5 H5 119.00 . . . no C4 C6 H6 120.00 . . . no C20 C6 H6 119.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no C8 C9 H9 120.00 . . . no C10 C9 H9 120.00 . . . no C9 C10 H10 120.00 . . . no C11 C10 H10 120.00 . . . no C10 C11 H11 120.00 . . . no C12 C11 H11 120.00 . . . no C7 C12 H12 120.00 . . . no C11 C12 H12 120.00 . . . no C2 C13 H13A 109.00 . . . no C2 C13 H13B 109.00 . . . no C14 C13 H13A 109.00 . . . no C14 C13 H13B 109.00 . . . no H13A C13 H13B 108.00 . . . no C13 C14 H14A 109.00 . . . no C13 C14 H14B 109.00 . . . no C15 C14 H14A 109.00 . . . no C15 C14 H14B 109.00 . . . no H14A C14 H14B 108.00 . . . no C14 C15 H15A 109.00 . . . no C14 C15 H15B 109.00 . . . no C16 C15 H15A 109.00 . . . no C16 C15 H15B 109.00 . . . no H15A C15 H15B 108.00 . . . no C1 C16 H16A 109.00 . . . no C1 C16 H16B 109.00 . . . no C15 C16 H16A 109.00 . . . no C15 C16 H16B 109.00 . . . no H16A C16 H16B 108.00 . . . no N1 C17 H17 107.00 . . . no C18 C17 H17 107.00 . . . no C21 C17 H17 107.00 . . . no C5 C19 H19 120.00 . . . no C18 C19 H19 120.00 2_655 . . no C6 C20 H20 119.00 . . . no C18 C20 H20 119.00 2_655 . . no C21 C22 H22 120.00 . . . no C23 C22 H22 120.00 . . . no C22 C23 H23 120.00 . . . no C24 C23 H23 120.00 . . . no C23 C24 H24 120.00 . . . no C25 C24 H24 120.00 . . . no C24 C25 H25 120.00 . . . no C26 C25 H25 120.00 . . . no C21 C26 H26 120.00 . . . no C25 C26 H26 119.00 . . . no N3 C27 C28 178.1(4) . . . yes C27 C28 H28A 109.00 . . . no C27 C28 H28B 109.00 . . . no C27 C28 H28C 109.00 . . . no H28A C28 H28B 109.00 . . . no H28A C28 H28C 110.00 . . . no H28B C28 H28C 110.00 . . . no N4 C29 C30 180.00(2) . . . yes N5 C31 C32 180.00 . . . yes 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 C17 N1 C1 C2 171.58(16) . . . . no C17 N1 C1 C16 -65.8(2) . . . . no C1 N1 C17 C18 -174.45(16) . . . . no C1 N1 C17 C21 -48.9(3) . . . . no C3 N2 C2 C1 177.88(18) . . . . no C3 N2 C2 C13 -59.2(2) . . . . no C2 N2 C3 C4 172.05(18) . . . . no C2 N2 C3 C7 -62.9(3) . . . . no N1 C1 C2 N2 -59.3(2) . . . . no N1 C1 C2 C13 175.88(16) . . . . no C16 C1 C2 N2 178.77(18) . . . . no C16 C1 C2 C13 53.9(2) . . . . no N1 C1 C16 C15 -174.78(17) . . . . no C2 C1 C16 C15 -54.1(2) . . . . no N2 C2 C13 C14 -175.85(18) . . . . no C1 C2 C13 C14 -54.8(2) . . . . no N2 C3 C4 C5 -135.0(2) . . . . no N2 C3 C4 C6 43.6(3) . . . . no C7 C3 C4 C5 101.9(3) . . . . no C7 C3 C4 C6 -79.5(3) . . . . no N2 C3 C7 C8 -52.1(3) . . . . no N2 C3 C7 C12 126.2(2) . . . . no C4 C3 C7 C8 70.2(3) . . . . no C4 C3 C7 C12 -111.5(2) . . . . no C3 C4 C5 C19 179.1(2) . . . . no C6 C4 C5 C19 0.4(3) . . . . no C3 C4 C6 C20 -179.1(2) . . . . no C5 C4 C6 C20 -0.4(3) . . . . no C4 C5 C19 C18 -0.8(3) . . . 2_655 no C4 C6 C20 C18 0.9(4) . . . 2_655 no C3 C7 C8 C9 178.7(2) . . . . no C12 C7 C8 C9 0.4(4) . . . . no C3 C7 C12 C11 -177.9(2) . . . . no C8 C7 C12 C11 0.4(4) . . . . no C7 C8 C9 C10 -0.8(4) . . . . no C8 C9 C10 C11 0.5(5) . . . . no C9 C10 C11 C12 0.3(4) . . . . no C10 C11 C12 C7 -0.8(4) . . . . no C2 C13 C14 C15 55.4(3) . . . . no C13 C14 C15 C16 -54.2(3) . . . . no C14 C15 C16 C1 54.1(2) . . . . no N1 C17 C18 C19 -129.7(2) . . . 3_665 no N1 C17 C18 C20 50.7(3) . . . 3_665 no C21 C17 C18 C19 102.2(2) . . . 3_665 no C21 C17 C18 C20 -77.4(3) . . . 3_665 no N1 C17 C21 C22 -38.9(3) . . . . no N1 C17 C21 C26 140.3(3) . . . . no C18 C17 C21 C22 87.2(3) . . . . no C18 C17 C21 C26 -93.6(3) . . . . no C17 C18 C19 C5 -178.4(2) . . 3_665 3_665 no C17 C18 C20 C6 178.3(2) . . 3_665 3_665 no C17 C21 C22 C23 178.6(3) . . . . no C26 C21 C22 C23 -0.7(4) . . . . no C17 C21 C26 C25 -179.3(3) . . . . no C22 C21 C26 C25 0.0(5) . . . . no C21 C22 C23 C24 0.4(5) . . . . no C22 C23 C24 C25 0.7(5) . . . . no C23 C24 C25 C26 -1.4(5) . . . . no C24 C25 C26 C21 1.0(5) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1N N2 0.87 2.36 2.807(3) 112 . yes N2 H2N N3 0.91 2.37 3.266(4) 166 2_655 yes _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.456 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.045