# 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 _publ_contact_author_name 'Xiu-Ping Yan' _publ_contact_author_email XPYAN@NANKAI.EDU.CN _publ_section_title ; Self-assembly of Intriguing Anion-directed Supramolecular Architectures from 5,6-Dihydrodiindolo[3,2-a:2',3'-c]phenazine as a Building Block ; _publ_contact_author 'Xiu-Ping Yan' _publ_contact_author_address ; Research Center for Analytical Science, College of Chemistry Nankai University 94 Weijin Road, Tianjin 300071 (China) ; loop_ _publ_author_name 'Xiu-Ping Yan' 'Ting Wang' 'He-Fang Wang' # Attachment 'all.cif' # ---------------Attachment 'DIPZ.CIF' data_r81104d _database_code_depnum_ccdc_archive 'CCDC 736336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; DIPZ ; _chemical_name_common DIPZ _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 N4 O2' _chemical_formula_weight 446.50 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9968(16) _cell_length_b 11.764(2) _cell_length_c 11.929(2) _cell_angle_alpha 74.18(3) _cell_angle_beta 88.87(3) _cell_angle_gamma 89.89(3) _cell_volume 1079.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2121 _cell_measurement_theta_min 1.775 _cell_measurement_theta_max 27.872 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9842 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6832 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3779 _reflns_number_gt 2453 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The restraints are made to refine the bond length of N-H in the two indole groups in DIPZ. The length is fixed at 0.90 as the theoretical bond length of N-H. ; _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^)+(0.0649P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3779 _refine_ls_number_parameters 317 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0969 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 N1 N 0.7296(2) 0.94825(16) -0.09867(17) 0.0198(5) Uani 1 1 d D . . N2 N 0.4177(2) 0.67134(16) 0.17950(17) 0.0201(5) Uani 1 1 d . . . N3 N 0.5001(2) 0.78070(15) 0.35834(17) 0.0195(5) Uani 1 1 d . . . N4 N 0.8084(2) 1.07505(16) 0.09584(18) 0.0203(5) Uani 1 1 d D . . C1 C 0.6651(3) 0.86505(19) -0.1498(2) 0.0176(5) Uani 1 1 d . . . C2 C 0.6871(3) 0.8566(2) -0.2632(2) 0.0209(6) Uani 1 1 d . . . H2 H 0.7506 0.9119 -0.3181 0.025 Uiso 1 1 calc R . . C3 C 0.6115(3) 0.7631(2) -0.2912(2) 0.0239(6) Uani 1 1 d . . . H3 H 0.6233 0.7554 -0.3665 0.029 Uiso 1 1 calc R . . C4 C 0.5170(3) 0.6796(2) -0.2081(2) 0.0242(6) Uani 1 1 d . . . H4A H 0.4682 0.6169 -0.2292 0.029 Uiso 1 1 calc R . . C5 C 0.4946(3) 0.6879(2) -0.0958(2) 0.0205(6) Uani 1 1 d . . . H5 H 0.4311 0.6319 -0.0417 0.025 Uiso 1 1 calc R . . C6 C 0.5689(3) 0.78208(19) -0.0646(2) 0.0170(5) Uani 1 1 d . . . C7 C 0.5767(3) 0.81935(19) 0.0410(2) 0.0180(5) Uani 1 1 d . . . C8 C 0.5105(3) 0.76981(19) 0.1566(2) 0.0169(5) Uani 1 1 d . . . C9 C 0.3643(3) 0.6262(2) 0.2926(2) 0.0194(6) Uani 1 1 d . . . C10 C 0.2641(3) 0.5227(2) 0.3215(2) 0.0225(6) Uani 1 1 d . . . H10 H 0.2339 0.4877 0.2637 0.027 Uiso 1 1 calc R . . C11 C 0.2118(3) 0.4742(2) 0.4340(2) 0.0249(6) Uani 1 1 d . . . H11 H 0.1453 0.4066 0.4520 0.030 Uiso 1 1 calc R . . C12 C 0.2572(3) 0.5251(2) 0.5235(2) 0.0250(6) Uani 1 1 d . . . H12 H 0.2224 0.4902 0.6000 0.030 Uiso 1 1 calc R . . C13 C 0.3520(3) 0.6256(2) 0.4978(2) 0.0233(6) Uani 1 1 d . . . H13 H 0.3804 0.6592 0.5570 0.028 Uiso 1 1 calc R . . C14 C 0.4080(3) 0.67939(19) 0.3815(2) 0.0178(5) Uani 1 1 d . . . C15 C 0.5494(3) 0.82679(19) 0.2473(2) 0.0182(6) Uani 1 1 d . . . C16 C 0.6488(3) 0.93223(19) 0.2164(2) 0.0177(5) Uani 1 1 d . . . C17 C 0.7111(3) 1.00831(19) 0.2833(2) 0.0190(6) Uani 1 1 d . . . C18 C 0.6941(3) 1.0114(2) 0.3992(2) 0.0225(6) Uani 1 1 d . . . H18 H 0.6290 0.9552 0.4519 0.027 Uiso 1 1 calc R . . C19 C 0.7750(3) 1.0988(2) 0.4345(2) 0.0247(6) Uani 1 1 d . . . H19 H 0.7638 1.1014 0.5115 0.030 Uiso 1 1 calc R . . C20 C 0.8740(3) 1.1837(2) 0.3559(2) 0.0266(6) Uani 1 1 d . . . H20 H 0.9283 1.2413 0.3820 0.032 Uiso 1 1 calc R . . C21 C 0.8927(3) 1.1836(2) 0.2409(2) 0.0229(6) Uani 1 1 d . . . H21 H 0.9580 1.2403 0.1890 0.027 Uiso 1 1 calc R . . C22 C 0.8104(3) 1.09570(19) 0.2050(2) 0.0186(6) Uani 1 1 d . . . C23 C 0.7111(3) 0.97788(19) 0.1027(2) 0.0168(5) Uani 1 1 d . . . C24 C 0.6753(3) 0.92095(19) 0.0152(2) 0.0167(5) Uani 1 1 d . . . O1 O -0.0772(2) 0.16071(14) 0.85510(14) 0.0252(5) Uani 1 1 d . . . O2 O 0.0811(2) 0.32314(13) 0.79192(14) 0.0243(4) Uani 1 1 d . . . C25 C 0.0194(3) 0.2190(2) 0.6556(2) 0.0266(6) Uani 1 1 d . . . H25A H -0.0147 0.1415 0.6532 0.040 Uiso 1 1 calc R . . H25B H 0.1340 0.2321 0.6299 0.040 Uiso 1 1 calc R . . H25C H -0.0498 0.2772 0.6054 0.040 Uiso 1 1 calc R . . C26 C 0.0019(3) 0.2287(2) 0.7771(2) 0.0202(6) Uani 1 1 d . . . C27 C 0.0607(3) 0.3452(2) 0.9057(2) 0.0267(6) Uani 1 1 d . . . H27A H 0.1001 0.2783 0.9664 0.032 Uiso 1 1 calc R . . H27B H -0.0562 0.3584 0.9215 0.032 Uiso 1 1 calc R . . C28 C 0.1630(3) 0.4539(2) 0.9015(3) 0.0363(7) Uani 1 1 d . . . H28A H 0.2778 0.4401 0.8843 0.054 Uiso 1 1 calc R . . H28B H 0.1549 0.4712 0.9755 0.054 Uiso 1 1 calc R . . H28C H 0.1214 0.5196 0.8419 0.054 Uiso 1 1 calc R . . H1 H 0.791(3) 1.0119(15) -0.134(2) 0.031(7) Uiso 1 1 d D . . H4 H 0.854(3) 1.1202(19) 0.0286(14) 0.032(8) Uiso 1 1 d 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 N1 0.0216(11) 0.0183(10) 0.0185(12) -0.0036(9) 0.0035(9) -0.0072(9) N2 0.0204(11) 0.0193(10) 0.0202(12) -0.0048(9) 0.0015(9) -0.0001(9) N3 0.0202(11) 0.0169(10) 0.0212(12) -0.0050(9) -0.0017(9) -0.0005(9) N4 0.0206(11) 0.0191(10) 0.0207(12) -0.0046(9) 0.0013(9) -0.0053(9) C1 0.0168(12) 0.0169(11) 0.0200(14) -0.0065(10) -0.0020(10) 0.0000(10) C2 0.0235(13) 0.0215(12) 0.0175(14) -0.0054(10) 0.0008(11) -0.0006(11) C3 0.0266(14) 0.0277(13) 0.0189(14) -0.0089(11) 0.0004(11) 0.0011(12) C4 0.0270(14) 0.0228(12) 0.0261(15) -0.0123(11) -0.0025(12) -0.0031(11) C5 0.0224(13) 0.0198(12) 0.0214(14) -0.0089(10) -0.0002(11) -0.0022(11) C6 0.0169(12) 0.0192(11) 0.0155(13) -0.0059(10) -0.0001(10) 0.0004(10) C7 0.0185(12) 0.0173(11) 0.0183(13) -0.0051(10) -0.0010(10) 0.0003(10) C8 0.0165(12) 0.0136(11) 0.0206(14) -0.0046(10) 0.0000(10) 0.0009(10) C9 0.0168(12) 0.0191(11) 0.0203(14) -0.0019(10) 0.0010(10) 0.0020(10) C10 0.0230(13) 0.0212(12) 0.0228(14) -0.0050(11) 0.0002(11) -0.0030(11) C11 0.0233(14) 0.0195(12) 0.0296(15) -0.0034(11) 0.0043(12) -0.0047(11) C12 0.0239(14) 0.0261(13) 0.0210(14) 0.0003(11) 0.0041(11) -0.0033(11) C13 0.0231(13) 0.0254(13) 0.0218(14) -0.0073(11) 0.0018(11) 0.0015(11) C14 0.0166(12) 0.0176(11) 0.0198(14) -0.0064(10) 0.0006(10) -0.0006(10) C15 0.0160(12) 0.0187(12) 0.0199(14) -0.0052(10) -0.0006(10) 0.0034(10) C16 0.0192(12) 0.0178(11) 0.0169(13) -0.0060(10) 0.0001(10) 0.0017(10) C17 0.0187(12) 0.0205(12) 0.0186(14) -0.0066(10) 0.0003(10) 0.0015(10) C18 0.0236(13) 0.0228(12) 0.0219(15) -0.0073(11) -0.0027(11) 0.0003(11) C19 0.0307(15) 0.0273(13) 0.0201(14) -0.0129(11) -0.0048(12) 0.0007(12) C20 0.0281(15) 0.0254(13) 0.0297(16) -0.0133(12) -0.0047(12) -0.0043(12) C21 0.0238(13) 0.0181(12) 0.0284(16) -0.0089(11) -0.0025(11) -0.0030(11) C22 0.0188(12) 0.0205(12) 0.0174(14) -0.0065(10) -0.0018(10) 0.0021(10) C23 0.0155(12) 0.0154(11) 0.0197(13) -0.0048(10) -0.0031(10) 0.0005(10) C24 0.0150(12) 0.0192(11) 0.0155(13) -0.0041(10) 0.0014(10) 0.0023(10) O1 0.0283(10) 0.0221(9) 0.0225(10) -0.0018(8) 0.0034(8) -0.0068(8) O2 0.0261(10) 0.0202(8) 0.0254(10) -0.0046(8) 0.0031(8) -0.0071(8) C25 0.0302(15) 0.0253(13) 0.0231(15) -0.0042(12) -0.0031(12) 0.0014(12) C26 0.0165(12) 0.0176(12) 0.0242(15) -0.0014(11) -0.0047(11) 0.0015(10) C27 0.0292(15) 0.0278(13) 0.0251(15) -0.0108(12) 0.0008(12) 0.0002(12) C28 0.0356(16) 0.0304(14) 0.0473(19) -0.0181(13) 0.0012(14) -0.0042(13) _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 N1 C24 1.370(3) . ? N1 C1 1.391(3) . ? N1 H1 0.896(10) . ? N2 C8 1.338(3) . ? N2 C9 1.368(3) . ? N3 C15 1.339(3) . ? N3 C14 1.362(3) . ? N4 C23 1.367(3) . ? N4 C22 1.389(3) . ? N4 H4 0.903(10) . ? C1 C2 1.392(3) . ? C1 C6 1.417(3) . ? C2 C3 1.377(3) . ? C2 H2 0.9300 . ? C3 C4 1.401(3) . ? C3 H3 0.9300 . ? C4 C5 1.377(3) . ? C4 H4A 0.9300 . ? C5 C6 1.399(3) . ? C5 H5 0.9300 . ? C6 C7 1.445(3) . ? C7 C24 1.392(3) . ? C7 C8 1.433(3) . ? C8 C15 1.458(3) . ? C9 C10 1.417(3) . ? C9 C14 1.420(3) . ? C10 C11 1.365(3) . ? C10 H10 0.9300 . ? C11 C12 1.413(4) . ? C11 H11 0.9300 . ? C12 C13 1.365(3) . ? C12 H12 0.9300 . ? C13 C14 1.422(3) . ? C13 H13 0.9300 . ? C15 C16 1.431(3) . ? C16 C23 1.398(3) . ? C16 C17 1.446(3) . ? C17 C18 1.397(3) . ? C17 C22 1.417(3) . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C19 C20 1.402(4) . ? C19 H19 0.9300 . ? C20 C21 1.377(4) . ? C20 H20 0.9300 . ? C21 C22 1.393(3) . ? C21 H21 0.9300 . ? C23 C24 1.419(3) . ? O1 C26 1.216(3) . ? O2 C26 1.334(3) . ? O2 C27 1.456(3) . ? C25 C26 1.489(3) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C27 C28 1.508(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 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 C24 N1 C1 108.6(2) . . ? C24 N1 H1 124.9(17) . . ? C1 N1 H1 126.4(17) . . ? C8 N2 C9 116.4(2) . . ? C15 N3 C14 116.4(2) . . ? C23 N4 C22 108.6(2) . . ? C23 N4 H4 123.5(17) . . ? C22 N4 H4 127.6(17) . . ? N1 C1 C2 129.1(2) . . ? N1 C1 C6 108.5(2) . . ? C2 C1 C6 122.4(2) . . ? C3 C2 C1 117.5(2) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C2 C3 C4 121.0(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 121.6(2) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? C4 C5 C6 118.9(2) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C1 118.6(2) . . ? C5 C6 C7 135.2(2) . . ? C1 C6 C7 106.2(2) . . ? C24 C7 C8 120.7(2) . . ? C24 C7 C6 106.7(2) . . ? C8 C7 C6 132.6(2) . . ? N2 C8 C7 119.5(2) . . ? N2 C8 C15 121.5(2) . . ? C7 C8 C15 119.0(2) . . ? N2 C9 C10 118.8(2) . . ? N2 C9 C14 121.9(2) . . ? C10 C9 C14 119.3(2) . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.9(2) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.7(3) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? N3 C14 C9 121.9(2) . . ? N3 C14 C13 119.3(2) . . ? C9 C14 C13 118.8(2) . . ? N3 C15 C16 119.7(2) . . ? N3 C15 C8 121.8(2) . . ? C16 C15 C8 118.5(2) . . ? C23 C16 C15 120.8(2) . . ? C23 C16 C17 106.4(2) . . ? C15 C16 C17 132.7(2) . . ? C18 C17 C22 119.0(2) . . ? C18 C17 C16 134.8(2) . . ? C22 C17 C16 106.2(2) . . ? C19 C18 C17 119.2(2) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 120.9(2) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C21 C20 C19 121.4(2) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C22 117.8(2) . . ? C20 C21 H21 121.1 . . ? C22 C21 H21 121.1 . . ? N4 C22 C21 129.6(2) . . ? N4 C22 C17 108.7(2) . . ? C21 C22 C17 121.8(2) . . ? N4 C23 C16 110.1(2) . . ? N4 C23 C24 129.4(2) . . ? C16 C23 C24 120.4(2) . . ? N1 C24 C7 110.0(2) . . ? N1 C24 C23 129.4(2) . . ? C7 C24 C23 120.6(2) . . ? C26 O2 C27 116.43(19) . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O1 C26 O2 122.6(2) . . ? O1 C26 C25 125.0(2) . . ? O2 C26 C25 112.4(2) . . ? O2 C27 C28 106.4(2) . . ? O2 C27 H27A 110.4 . . ? C28 C27 H27A 110.4 . . ? O2 C27 H27B 110.4 . . ? C28 C27 H27B 110.4 . . ? H27A C27 H27B 108.6 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 C24 N1 C1 C2 -179.6(2) . . . . ? C24 N1 C1 C6 -0.8(2) . . . . ? N1 C1 C2 C3 178.6(2) . . . . ? C6 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C4 C5 C6 C7 -178.9(2) . . . . ? N1 C1 C6 C5 -178.52(19) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? N1 C1 C6 C7 0.5(2) . . . . ? C2 C1 C6 C7 179.4(2) . . . . ? C5 C6 C7 C24 178.7(2) . . . . ? C1 C6 C7 C24 -0.1(2) . . . . ? C5 C6 C7 C8 1.3(4) . . . . ? C1 C6 C7 C8 -177.5(2) . . . . ? C9 N2 C8 C7 177.41(19) . . . . ? C9 N2 C8 C15 -1.2(3) . . . . ? C24 C7 C8 N2 -179.2(2) . . . . ? C6 C7 C8 N2 -2.1(4) . . . . ? C24 C7 C8 C15 -0.6(3) . . . . ? C6 C7 C8 C15 176.5(2) . . . . ? C8 N2 C9 C10 179.35(19) . . . . ? C8 N2 C9 C14 -1.4(3) . . . . ? N2 C9 C10 C11 178.6(2) . . . . ? C14 C9 C10 C11 -0.7(3) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 C13 1.3(3) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C15 N3 C14 C9 -0.9(3) . . . . ? C15 N3 C14 C13 179.8(2) . . . . ? N2 C9 C14 N3 2.5(3) . . . . ? C10 C9 C14 N3 -178.19(19) . . . . ? N2 C9 C14 C13 -178.2(2) . . . . ? C10 C9 C14 C13 1.1(3) . . . . ? C12 C13 C14 N3 178.9(2) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? C14 N3 C15 C16 -179.07(19) . . . . ? C14 N3 C15 C8 -1.7(3) . . . . ? N2 C8 C15 N3 2.8(3) . . . . ? C7 C8 C15 N3 -175.75(19) . . . . ? N2 C8 C15 C16 -179.73(19) . . . . ? C7 C8 C15 C16 1.7(3) . . . . ? N3 C15 C16 C23 175.8(2) . . . . ? C8 C15 C16 C23 -1.7(3) . . . . ? N3 C15 C16 C17 -1.5(4) . . . . ? C8 C15 C16 C17 -179.0(2) . . . . ? C23 C16 C17 C18 179.6(2) . . . . ? C15 C16 C17 C18 -2.9(4) . . . . ? C23 C16 C17 C22 -0.7(2) . . . . ? C15 C16 C17 C22 176.8(2) . . . . ? C22 C17 C18 C19 -0.4(3) . . . . ? C16 C17 C18 C19 179.3(2) . . . . ? C17 C18 C19 C20 -0.3(3) . . . . ? C18 C19 C20 C21 0.6(4) . . . . ? C19 C20 C21 C22 -0.3(3) . . . . ? C23 N4 C22 C21 179.5(2) . . . . ? C23 N4 C22 C17 0.1(2) . . . . ? C20 C21 C22 N4 -179.7(2) . . . . ? C20 C21 C22 C17 -0.3(3) . . . . ? C18 C17 C22 N4 -179.82(19) . . . . ? C16 C17 C22 N4 0.4(2) . . . . ? C18 C17 C22 C21 0.7(3) . . . . ? C16 C17 C22 C21 -179.1(2) . . . . ? C22 N4 C23 C16 -0.6(2) . . . . ? C22 N4 C23 C24 -178.1(2) . . . . ? C15 C16 C23 N4 -177.09(18) . . . . ? C17 C16 C23 N4 0.8(2) . . . . ? C15 C16 C23 C24 0.7(3) . . . . ? C17 C16 C23 C24 178.56(18) . . . . ? C1 N1 C24 C7 0.7(2) . . . . ? C1 N1 C24 C23 178.3(2) . . . . ? C8 C7 C24 N1 177.36(19) . . . . ? C6 C7 C24 N1 -0.4(2) . . . . ? C8 C7 C24 C23 -0.5(3) . . . . ? C6 C7 C24 C23 -178.23(18) . . . . ? N4 C23 C24 N1 0.4(4) . . . . ? C16 C23 C24 N1 -176.9(2) . . . . ? N4 C23 C24 C7 177.7(2) . . . . ? C16 C23 C24 C7 0.4(3) . . . . ? C27 O2 C26 O1 -3.3(3) . . . . ? C27 O2 C26 C25 175.49(18) . . . . ? C26 O2 C27 C28 179.04(18) . . . . ? 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 H1 O1 0.896(10) 2.019(14) 2.858(3) 156(2) 1_664 N4 H4 O1 0.903(10) 2.057(15) 2.902(3) 155(2) 1_664 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.191 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.051 # ---------------Attachment 'DIPZ-HSO4.CIF' data_b _database_code_depnum_ccdc_archive 'CCDC 736338' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DIPZ+HSO4 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H51 N5 O4 S' _chemical_formula_weight 697.92 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 41.692(8) _cell_length_b 8.3351(17) _cell_length_c 22.227(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.70(3) _cell_angle_gamma 90.00 _cell_volume 7686(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17024 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.53 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2992 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9744 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rigaku r-aixs rapid IP area detector' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type oscillation _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29260 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_h_max 49 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6768 _reflns_number_gt 4429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'rapid auto' _computing_cell_refinement 'rapid auto' _computing_data_reduction 'rapid auto' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. These restraints are made to refine the bond length of ortho C-C(1.54) in tetrabutylammonium cation, the bond length of N-H(0.90) in indole and the bond length of S-O, fixing them close to the theoretical bond length. ; _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^)+(0.1146P)^2^+5.3528P] 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 0.0012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6768 _refine_ls_number_parameters 516 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1007 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.2171 _refine_ls_wR_factor_gt 0.1930 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.13674(7) 0.0372(4) 0.88686(13) 0.0560(7) Uani 1 1 d . . . C2 C 0.15569(7) 0.0343(4) 0.98349(13) 0.0557(7) Uani 1 1 d . . . C3 C 0.15928(9) 0.0184(4) 1.04600(14) 0.0648(8) Uani 1 1 d . . . C4 C 0.18854(9) 0.0562(4) 1.07615(15) 0.0702(9) Uani 1 1 d . . . C5 C 0.21397(10) 0.1076(5) 1.04507(15) 0.0755(10) Uani 1 1 d . . . C6 C 0.21056(8) 0.1244(4) 0.98292(14) 0.0662(8) Uani 1 1 d . . . C7 C 0.18089(7) 0.0889(4) 0.95122(12) 0.0552(7) Uani 1 1 d . . . C8 C 0.16824(7) 0.0924(3) 0.88872(12) 0.0535(7) Uani 1 1 d . . . C9 C 0.18137(7) 0.1415(4) 0.83450(12) 0.0542(7) Uani 1 1 d . . . C10 C 0.22229(7) 0.2395(4) 0.78424(13) 0.0597(8) Uani 1 1 d . . . C11 C 0.25448(8) 0.2947(5) 0.78437(16) 0.0739(10) Uani 1 1 d . . . C12 C 0.26594(9) 0.3406(5) 0.73221(17) 0.0809(10) Uani 1 1 d . . . C13 C 0.24641(10) 0.3347(5) 0.67784(17) 0.0810(11) Uani 1 1 d . . . C14 C 0.21562(9) 0.2821(5) 0.67544(16) 0.0731(9) Uani 1 1 d . . . C15 C 0.20263(7) 0.2307(4) 0.72906(13) 0.0587(7) Uani 1 1 d . . . C16 C 0.16112(7) 0.1315(3) 0.77756(12) 0.0524(7) Uani 1 1 d . . . C17 C 0.12893(7) 0.0730(4) 0.77774(12) 0.0546(7) Uani 1 1 d . . . C18 C 0.10340(7) 0.0468(4) 0.73064(13) 0.0590(7) Uani 1 1 d . . . C19 C 0.09991(9) 0.0670(4) 0.66802(14) 0.0672(9) Uani 1 1 d . . . C20 C 0.07132(10) 0.0251(5) 0.63579(18) 0.0829(11) Uani 1 1 d . . . C21 C 0.04595(11) -0.0351(6) 0.6652(2) 0.0924(13) Uani 1 1 d . . . C22 C 0.04834(9) -0.0549(6) 0.72636(19) 0.0839(11) Uani 1 1 d . . . C23 C 0.07721(7) -0.0146(4) 0.75872(14) 0.0664(8) Uani 1 1 d . . . C24 C 0.11711(7) 0.0259(4) 0.83094(13) 0.0562(7) Uani 1 1 d . . . C25 C 0.11955(10) 0.3588(5) 0.10733(19) 0.0902(11) Uani 1 1 d . . . H25A H 0.1032 0.2798 0.1140 0.108 Uiso 1 1 calc R . . H25B H 0.1378 0.3016 0.0940 0.108 Uiso 1 1 calc R . . C26 C 0.13017(12) 0.4384(5) 0.1669(2) 0.1019(13) Uani 1 1 d . . . H26A H 0.1452 0.5236 0.1601 0.122 Uiso 1 1 calc R . . H26B H 0.1115 0.4870 0.1825 0.122 Uiso 1 1 calc R . . C27 C 0.14544(15) 0.3288(6) 0.2125(3) 0.1276(18) Uani 1 1 d . . . H27A H 0.1644 0.2841 0.1968 0.153 Uiso 1 1 calc R . . H27B H 0.1307 0.2407 0.2169 0.153 Uiso 1 1 calc R . . C28 C 0.15531(15) 0.3930(7) 0.2731(2) 0.1300(18) Uani 1 1 d . . . H28A H 0.1743 0.4573 0.2718 0.195 Uiso 1 1 calc R . . H28B H 0.1598 0.3058 0.3009 0.195 Uiso 1 1 calc R . . H28C H 0.1383 0.4578 0.2861 0.195 Uiso 1 1 calc R . . C29 C 0.07672(10) 0.5610(5) 0.0749(2) 0.0879(11) Uani 1 1 d . . . H29A H 0.0831 0.6193 0.1119 0.105 Uiso 1 1 calc R . . H29B H 0.0703 0.6395 0.0437 0.105 Uiso 1 1 calc R . . C30 C 0.04817(12) 0.4590(6) 0.0845(3) 0.1215(16) Uani 1 1 d . . . H30A H 0.0551 0.3697 0.1106 0.146 Uiso 1 1 calc R . . H30B H 0.0392 0.4155 0.0460 0.146 Uiso 1 1 calc R . . C31 C 0.02220(15) 0.5518(9) 0.1127(3) 0.145(2) Uani 1 1 d . . . H31A H 0.0197 0.6562 0.0935 0.174 Uiso 1 1 calc R . . H31B H 0.0019 0.4951 0.1051 0.174 Uiso 1 1 calc R . . C32 C 0.0293(2) 0.5730(11) 0.1756(3) 0.189(3) Uani 1 1 d . . . H32A H 0.0262 0.4734 0.1959 0.283 Uiso 1 1 calc R . . H32B H 0.0152 0.6529 0.1896 0.283 Uiso 1 1 calc R . . H32C H 0.0512 0.6071 0.1841 0.283 Uiso 1 1 calc R . . C33 C 0.09609(11) 0.3672(5) 0.0011(2) 0.0962(12) Uani 1 1 d . . . H33A H 0.1148 0.3086 -0.0095 0.115 Uiso 1 1 calc R . . H33B H 0.0804 0.2890 0.0118 0.115 Uiso 1 1 calc R . . C34 C 0.08185(14) 0.4587(7) -0.0540(2) 0.1242(18) Uani 1 1 d . . . H34A H 0.0600 0.4903 -0.0478 0.149 Uiso 1 1 calc R . . H34B H 0.0943 0.5559 -0.0578 0.149 Uiso 1 1 calc R . . C35 C 0.08111(18) 0.3709(8) -0.1091(3) 0.157(2) Uani 1 1 d . . . H35A H 0.0676 0.2774 -0.1056 0.189 Uiso 1 1 calc R . . H35B H 0.1028 0.3324 -0.1130 0.189 Uiso 1 1 calc R . . C36 C 0.06955(18) 0.4553(10) -0.1659(3) 0.170(3) Uani 1 1 d . . . H36A H 0.0498 0.5105 -0.1606 0.255 Uiso 1 1 calc R . . H36B H 0.0658 0.3787 -0.1981 0.255 Uiso 1 1 calc R . . H36C H 0.0855 0.5313 -0.1757 0.255 Uiso 1 1 calc R . . C37 C 0.13103(10) 0.5907(5) 0.0425(2) 0.0894(11) Uani 1 1 d . . . H37A H 0.1361 0.6572 0.0780 0.107 Uiso 1 1 calc R . . H37B H 0.1217 0.6598 0.0103 0.107 Uiso 1 1 calc R . . C38 C 0.16185(13) 0.5215(7) 0.0241(3) 0.1312(19) Uani 1 1 d . . . H38A H 0.1754 0.4909 0.0603 0.157 Uiso 1 1 calc R . . H38B H 0.1568 0.4247 0.0008 0.157 Uiso 1 1 calc R . . C39 C 0.1799(2) 0.6271(8) -0.0110(5) 0.223(5) Uani 1 1 d D . . H39A H 0.1640 0.6802 -0.0392 0.268 Uiso 1 1 calc R . . H39B H 0.1886 0.7093 0.0168 0.268 Uiso 1 1 calc R . . C40 C 0.2052(3) 0.5827(10) -0.0450(5) 0.250(5) Uani 1 1 d D . . H40A H 0.2188 0.5061 -0.0227 0.375 Uiso 1 1 calc R . . H40B H 0.2176 0.6760 -0.0531 0.375 Uiso 1 1 calc R . . H40C H 0.1965 0.5358 -0.0826 0.375 Uiso 1 1 calc R . . H1 H 0.1102(5) -0.032(4) 0.9543(17) 0.096(12) Uiso 1 1 d D . . H2 H 0.0731(7) -0.059(4) 0.8470(12) 0.075(10) Uiso 1 1 d D . . H3 H 0.1408(8) -0.019(3) 1.0648(13) 0.061(8) Uiso 1 1 d . . . H4 H 0.1914(8) 0.044(4) 1.1178(17) 0.076(10) Uiso 1 1 d . . . H5 H 0.2353(9) 0.124(4) 1.0668(17) 0.091(11) Uiso 1 1 d . . . H6 H 0.2281(8) 0.158(4) 0.9572(14) 0.072(9) Uiso 1 1 d . . . H11 H 0.2674(8) 0.291(4) 0.8218(15) 0.073(10) Uiso 1 1 d . . . H12 H 0.2896(11) 0.384(5) 0.7324(18) 0.107(13) Uiso 1 1 d . . . H13 H 0.2540(9) 0.362(5) 0.6439(18) 0.095(12) Uiso 1 1 d . . . H14 H 0.2030(8) 0.270(4) 0.6384(15) 0.069(9) Uiso 1 1 d . . . H19 H 0.1174(8) 0.108(4) 0.6501(14) 0.064(9) Uiso 1 1 d . . . H20 H 0.0708(8) 0.044(4) 0.5913(17) 0.079(10) Uiso 1 1 d . . . H21 H 0.0291(11) -0.059(5) 0.6420(19) 0.102(14) Uiso 1 1 d . . . H22 H 0.0338(9) -0.098(4) 0.7466(15) 0.068(10) Uiso 1 1 d . . . H3A H -0.0043(17) 0.138(8) 0.500(3) 0.19(2) Uiso 1 1 d . . . N1 N 0.12926(6) 0.0020(3) 0.94357(11) 0.0597(6) Uani 1 1 d D . . N2 N 0.08618(6) -0.0269(4) 0.81991(12) 0.0678(7) Uani 1 1 d D . . N3 N 0.17200(6) 0.1769(3) 0.72572(10) 0.0591(6) Uani 1 1 d . . . N4 N 0.21145(6) 0.1952(3) 0.83723(10) 0.0584(6) Uani 1 1 d . . . N5 N 0.10611(7) 0.4698(3) 0.05646(14) 0.0793(8) Uani 1 1 d . . . O1 O 0.07241(6) 0.1134(4) 0.47943(13) 0.1006(9) Uani 1 1 d D . . O2 O 0.03611(7) 0.0826(6) 0.39390(12) 0.1568(18) Uani 1 1 d D . . O3 O 0.01803(6) 0.1876(3) 0.48411(12) 0.0879(8) Uani 1 1 d D . . O4 O 0.03417(8) -0.0864(4) 0.4810(2) 0.1406(15) Uani 1 1 d D . . S1 S 0.040398(18) 0.07526(11) 0.45677(4) 0.0688(3) Uani 1 1 d 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 C1 0.0511(16) 0.0697(18) 0.0473(16) -0.0024(14) 0.0061(13) 0.0037(14) C2 0.0550(17) 0.0635(17) 0.0484(16) 0.0023(13) 0.0043(13) 0.0039(14) C3 0.076(2) 0.069(2) 0.0498(17) 0.0024(15) 0.0099(16) -0.0013(17) C4 0.085(3) 0.080(2) 0.0438(17) 0.0037(16) -0.0031(17) -0.0035(18) C5 0.072(2) 0.095(3) 0.057(2) 0.0016(18) -0.0101(17) -0.009(2) C6 0.0601(19) 0.086(2) 0.0507(17) 0.0012(16) -0.0009(15) -0.0041(17) C7 0.0560(17) 0.0628(17) 0.0460(15) -0.0008(13) 0.0007(13) 0.0012(14) C8 0.0474(16) 0.0673(18) 0.0453(15) -0.0027(13) 0.0017(12) 0.0025(14) C9 0.0514(17) 0.0636(17) 0.0476(16) -0.0046(13) 0.0046(13) 0.0030(14) C10 0.0574(17) 0.0707(19) 0.0515(17) -0.0042(14) 0.0070(13) -0.0046(15) C11 0.062(2) 0.098(3) 0.061(2) -0.0050(19) 0.0058(17) -0.0191(19) C12 0.069(2) 0.097(3) 0.077(2) -0.001(2) 0.0134(19) -0.026(2) C13 0.083(3) 0.101(3) 0.062(2) 0.005(2) 0.0188(19) -0.021(2) C14 0.076(2) 0.093(2) 0.0518(19) 0.0017(17) 0.0088(17) -0.0143(19) C15 0.0578(18) 0.0674(18) 0.0509(16) -0.0024(14) 0.0061(13) -0.0025(15) C16 0.0493(16) 0.0648(17) 0.0426(15) -0.0033(13) 0.0018(12) 0.0035(13) C17 0.0490(16) 0.0679(18) 0.0461(15) -0.0044(13) 0.0014(12) 0.0045(14) C18 0.0507(17) 0.0714(19) 0.0538(17) -0.0073(14) 0.0003(13) 0.0048(14) C19 0.066(2) 0.081(2) 0.0524(18) -0.0036(16) -0.0040(16) 0.0043(18) C20 0.084(3) 0.100(3) 0.061(2) -0.006(2) -0.016(2) 0.005(2) C21 0.068(3) 0.119(3) 0.083(3) -0.011(2) -0.025(2) -0.001(2) C22 0.056(2) 0.117(3) 0.076(3) -0.005(2) -0.0057(19) -0.010(2) C23 0.0501(17) 0.089(2) 0.0586(19) -0.0066(17) -0.0022(14) 0.0033(16) C24 0.0456(16) 0.0727(19) 0.0498(16) -0.0042(14) 0.0021(13) 0.0023(14) C25 0.089(3) 0.068(2) 0.111(3) 0.011(2) -0.001(2) 0.006(2) C26 0.119(4) 0.091(3) 0.094(3) 0.009(2) -0.002(3) 0.010(3) C27 0.149(5) 0.101(3) 0.125(4) 0.021(3) -0.027(3) -0.009(3) C28 0.146(5) 0.137(4) 0.105(4) 0.019(3) 0.002(3) 0.008(4) C29 0.090(3) 0.076(2) 0.098(3) 0.001(2) 0.013(2) 0.015(2) C30 0.089(3) 0.129(4) 0.150(4) -0.007(3) 0.026(3) -0.002(3) C31 0.121(4) 0.189(6) 0.130(5) 0.025(4) 0.034(4) 0.014(4) C32 0.193(7) 0.255(9) 0.121(5) 0.000(5) 0.031(5) 0.009(6) C33 0.094(3) 0.085(3) 0.107(3) -0.022(2) 0.000(2) 0.010(2) C34 0.131(4) 0.123(4) 0.113(4) -0.031(3) -0.015(3) 0.031(3) C35 0.201(7) 0.162(5) 0.107(4) -0.019(4) 0.003(4) 0.047(5) C36 0.161(6) 0.244(8) 0.105(4) -0.004(5) 0.011(4) 0.011(5) C37 0.096(3) 0.078(2) 0.095(3) -0.002(2) 0.012(2) -0.008(2) C38 0.105(4) 0.133(4) 0.162(5) -0.028(4) 0.046(3) -0.014(3) C39 0.204(8) 0.121(5) 0.374(13) 0.001(6) 0.178(9) 0.012(5) C40 0.295(12) 0.167(7) 0.320(13) -0.035(7) 0.197(11) -0.040(7) N1 0.0493(15) 0.0814(17) 0.0483(14) 0.0012(12) 0.0052(11) -0.0027(13) N2 0.0468(15) 0.100(2) 0.0561(16) -0.0035(14) 0.0051(12) -0.0066(14) N3 0.0571(15) 0.0720(16) 0.0482(13) -0.0019(12) 0.0060(11) 0.0006(12) N4 0.0520(14) 0.0755(16) 0.0474(13) -0.0035(11) 0.0037(10) -0.0057(12) N5 0.078(2) 0.0667(17) 0.092(2) -0.0034(15) 0.0052(16) 0.0057(15) O1 0.0534(14) 0.146(2) 0.102(2) -0.0328(18) 0.0046(13) 0.0059(15) O2 0.087(2) 0.325(6) 0.0576(17) -0.012(2) 0.0033(14) 0.041(3) O3 0.0694(16) 0.0900(17) 0.1081(19) -0.0045(14) 0.0270(14) 0.0131(13) O4 0.104(2) 0.084(2) 0.247(5) -0.001(2) 0.083(3) 0.0051(17) S1 0.0480(5) 0.0944(7) 0.0654(5) -0.0086(4) 0.0122(4) -0.0010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.360(4) . ? C1 C8 1.388(4) . ? C1 C24 1.422(4) . ? C2 N1 1.371(4) . ? C2 C3 1.389(4) . ? C2 C7 1.406(4) . ? C3 C4 1.369(5) . ? C3 H3 0.96(3) . ? C4 C5 1.389(5) . ? C4 H4 0.93(4) . ? C5 C6 1.382(5) . ? C5 H5 0.98(4) . ? C6 C7 1.393(4) . ? C6 H6 1.01(3) . ? C7 C8 1.436(4) . ? C8 C9 1.432(4) . ? C9 N4 1.328(4) . ? C9 C16 1.452(4) . ? C10 N4 1.354(4) . ? C10 C15 1.408(4) . ? C10 C11 1.418(4) . ? C11 C12 1.352(5) . ? C11 H11 0.94(3) . ? C12 C13 1.389(5) . ? C12 H12 1.05(4) . ? C13 C14 1.353(5) . ? C13 H13 0.88(4) . ? C14 C15 1.423(4) . ? C14 H14 0.94(3) . ? C15 N3 1.348(4) . ? C16 N3 1.334(3) . ? C16 C17 1.428(4) . ? C17 C24 1.382(4) . ? C17 C18 1.434(4) . ? C18 C19 1.395(4) . ? C18 C23 1.407(4) . ? C19 C20 1.374(5) . ? C19 H19 0.93(3) . ? C20 C21 1.391(6) . ? C20 H20 1.00(4) . ? C21 C22 1.362(6) . ? C21 H21 0.85(4) . ? C22 C23 1.381(5) . ? C22 H22 0.87(3) . ? C23 N2 1.378(4) . ? C24 N2 1.362(4) . ? C25 C26 1.508(6) . ? C25 N5 1.524(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.462(6) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.469(7) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.496(6) . ? C29 N5 1.532(5) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.516(7) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.411(8) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.513(6) . ? C33 N5 1.522(5) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.424(7) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.483(8) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 N5 1.502(5) . ? C37 C38 1.502(6) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.436(8) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.410(7) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? N1 H1 0.896(10) . ? N2 H2 0.893(10) . ? O1 S1 1.415(3) . ? O2 S1 1.392(3) . ? O3 S1 1.493(2) . ? O3 H3A 1.11(7) . ? O4 S1 1.484(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 N1 C1 C8 110.3(3) . . ? N1 C1 C24 129.1(3) . . ? C8 C1 C24 120.6(3) . . ? N1 C2 C3 129.0(3) . . ? N1 C2 C7 109.1(2) . . ? C3 C2 C7 122.0(3) . . ? C4 C3 C2 118.0(3) . . ? C4 C3 H3 125.0(18) . . ? C2 C3 H3 117.0(18) . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4 119(2) . . ? C5 C4 H4 120(2) . . ? C6 C5 C4 121.4(3) . . ? C6 C5 H5 118(2) . . ? C4 C5 H5 120(2) . . ? C5 C6 C7 118.8(3) . . ? C5 C6 H6 125.8(18) . . ? C7 C6 H6 115.3(18) . . ? C6 C7 C2 118.8(3) . . ? C6 C7 C8 135.0(3) . . ? C2 C7 C8 106.2(2) . . ? C1 C8 C9 120.6(3) . . ? C1 C8 C7 106.1(2) . . ? C9 C8 C7 133.3(3) . . ? N4 C9 C8 119.8(3) . . ? N4 C9 C16 121.6(2) . . ? C8 C9 C16 118.6(3) . . ? N4 C10 C15 121.9(3) . . ? N4 C10 C11 119.0(3) . . ? C15 C10 C11 119.2(3) . . ? C12 C11 C10 120.3(3) . . ? C12 C11 H11 123(2) . . ? C10 C11 H11 117(2) . . ? C11 C12 C13 120.6(4) . . ? C11 C12 H12 120(2) . . ? C13 C12 H12 119(2) . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 118(3) . . ? C12 C13 H13 120(3) . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 121.2(19) . . ? C15 C14 H14 118.4(19) . . ? N3 C15 C10 122.1(3) . . ? N3 C15 C14 119.4(3) . . ? C10 C15 C14 118.5(3) . . ? N3 C16 C17 120.0(2) . . ? N3 C16 C9 121.2(3) . . ? C17 C16 C9 118.8(2) . . ? C24 C17 C16 120.9(3) . . ? C24 C17 C18 106.2(3) . . ? C16 C17 C18 132.8(3) . . ? C19 C18 C23 118.5(3) . . ? C19 C18 C17 135.0(3) . . ? C23 C18 C17 106.5(3) . . ? C20 C19 C18 119.3(4) . . ? C20 C19 H19 123(2) . . ? C18 C19 H19 118(2) . . ? C19 C20 C21 120.5(4) . . ? C19 C20 H20 114(2) . . ? C21 C20 H20 125(2) . . ? C22 C21 C20 122.0(4) . . ? C22 C21 H21 123(3) . . ? C20 C21 H21 115(3) . . ? C21 C22 C23 117.6(4) . . ? C21 C22 H22 126(2) . . ? C23 C22 H22 117(2) . . ? N2 C23 C22 129.3(3) . . ? N2 C23 C18 108.6(3) . . ? C22 C23 C18 122.2(3) . . ? N2 C24 C17 110.4(3) . . ? N2 C24 C1 129.1(3) . . ? C17 C24 C1 120.4(3) . . ? C26 C25 N5 116.0(3) . . ? C26 C25 H25A 108.3 . . ? N5 C25 H25A 108.3 . . ? C26 C25 H25B 108.3 . . ? N5 C25 H25B 108.3 . . ? H25A C25 H25B 107.4 . . ? C27 C26 C25 113.8(4) . . ? C27 C26 H26A 108.8 . . ? C25 C26 H26A 108.8 . . ? C27 C26 H26B 108.8 . . ? C25 C26 H26B 108.8 . . ? H26A C26 H26B 107.7 . . ? C26 C27 C28 118.1(5) . . ? C26 C27 H27A 107.8 . . ? C28 C27 H27A 107.8 . . ? C26 C27 H27B 107.8 . . ? C28 C27 H27B 107.8 . . ? H27A C27 H27B 107.1 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 N5 115.2(3) . . ? C30 C29 H29A 108.5 . . ? N5 C29 H29A 108.5 . . ? C30 C29 H29B 108.5 . . ? N5 C29 H29B 108.5 . . ? H29A C29 H29B 107.5 . . ? C29 C30 C31 112.4(5) . . ? C29 C30 H30A 109.1 . . ? C31 C30 H30A 109.1 . . ? C29 C30 H30B 109.1 . . ? C31 C30 H30B 109.1 . . ? H30A C30 H30B 107.9 . . ? C32 C31 C30 112.7(6) . . ? C32 C31 H31A 109.0 . . ? C30 C31 H31A 109.0 . . ? C32 C31 H31B 109.0 . . ? C30 C31 H31B 109.0 . . ? H31A C31 H31B 107.8 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 N5 115.2(4) . . ? C34 C33 H33A 108.5 . . ? N5 C33 H33A 108.5 . . ? C34 C33 H33B 108.5 . . ? N5 C33 H33B 108.5 . . ? H33A C33 H33B 107.5 . . ? C35 C34 C33 114.2(5) . . ? C35 C34 H34A 108.7 . . ? C33 C34 H34A 108.7 . . ? C35 C34 H34B 108.7 . . ? C33 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C34 C35 C36 117.8(6) . . ? C34 C35 H35A 107.9 . . ? C36 C35 H35A 107.9 . . ? C34 C35 H35B 107.9 . . ? C36 C35 H35B 107.9 . . ? H35A C35 H35B 107.2 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N5 C37 C38 115.3(3) . . ? N5 C37 H37A 108.5 . . ? C38 C37 H37A 108.5 . . ? N5 C37 H37B 108.5 . . ? C38 C37 H37B 108.5 . . ? H37A C37 H37B 107.5 . . ? C39 C38 C37 114.8(5) . . ? C39 C38 H38A 108.6 . . ? C37 C38 H38A 108.6 . . ? C39 C38 H38B 108.6 . . ? C37 C38 H38B 108.6 . . ? H38A C38 H38B 107.5 . . ? C40 C39 C38 126.2(6) . . ? C40 C39 H39A 105.8 . . ? C38 C39 H39A 105.8 . . ? C40 C39 H39B 105.8 . . ? C38 C39 H39B 105.8 . . ? H39A C39 H39B 106.2 . . ? 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 . . ? C1 N1 C2 108.3(2) . . ? C1 N1 H1 127(3) . . ? C2 N1 H1 124(3) . . ? C24 N2 C23 108.2(3) . . ? C24 N2 H2 127(2) . . ? C23 N2 H2 124(2) . . ? C16 N3 C15 116.6(2) . . ? C9 N4 C10 116.6(2) . . ? C37 N5 C33 110.5(3) . . ? C37 N5 C25 110.5(3) . . ? C33 N5 C25 108.0(3) . . ? C37 N5 C29 108.1(3) . . ? C33 N5 C29 109.4(3) . . ? C25 N5 C29 110.4(3) . . ? S1 O3 H3A 118(3) . . ? O2 S1 O1 111.7(2) . . ? O2 S1 O4 113.3(3) . . ? O1 S1 O4 105.5(2) . . ? O2 S1 O3 111.0(2) . . ? O1 S1 O3 108.64(17) . . ? O4 S1 O3 106.43(16) . . ? 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 N1 C2 C3 C4 179.0(3) . . . . ? C7 C2 C3 C4 -0.6(5) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C3 C4 C5 C6 0.9(6) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? C5 C6 C7 C2 -1.3(5) . . . . ? C5 C6 C7 C8 179.5(3) . . . . ? N1 C2 C7 C6 -178.1(3) . . . . ? C3 C2 C7 C6 1.6(5) . . . . ? N1 C2 C7 C8 1.3(3) . . . . ? C3 C2 C7 C8 -179.0(3) . . . . ? N1 C1 C8 C9 -178.2(3) . . . . ? C24 C1 C8 C9 1.1(4) . . . . ? N1 C1 C8 C7 0.6(3) . . . . ? C24 C1 C8 C7 179.8(3) . . . . ? C6 C7 C8 C1 178.1(4) . . . . ? C2 C7 C8 C1 -1.2(3) . . . . ? C6 C7 C8 C9 -3.3(6) . . . . ? C2 C7 C8 C9 177.4(3) . . . . ? C1 C8 C9 N4 179.4(3) . . . . ? C7 C8 C9 N4 1.0(5) . . . . ? C1 C8 C9 C16 -0.4(4) . . . . ? C7 C8 C9 C16 -178.8(3) . . . . ? N4 C10 C11 C12 -179.6(3) . . . . ? C15 C10 C11 C12 1.0(5) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 C14 -0.5(7) . . . . ? C12 C13 C14 C15 -0.2(6) . . . . ? N4 C10 C15 N3 -0.4(5) . . . . ? C11 C10 C15 N3 179.0(3) . . . . ? N4 C10 C15 C14 178.9(3) . . . . ? C11 C10 C15 C14 -1.8(5) . . . . ? C13 C14 C15 N3 -179.3(3) . . . . ? C13 C14 C15 C10 1.4(5) . . . . ? N4 C9 C16 N3 -0.3(4) . . . . ? C8 C9 C16 N3 179.4(3) . . . . ? N4 C9 C16 C17 -179.9(3) . . . . ? C8 C9 C16 C17 -0.1(4) . . . . ? N3 C16 C17 C24 -179.7(3) . . . . ? C9 C16 C17 C24 -0.2(4) . . . . ? N3 C16 C17 C18 1.3(5) . . . . ? C9 C16 C17 C18 -179.2(3) . . . . ? C24 C17 C18 C19 -178.9(3) . . . . ? C16 C17 C18 C19 0.2(6) . . . . ? C24 C17 C18 C23 0.3(3) . . . . ? C16 C17 C18 C23 179.4(3) . . . . ? C23 C18 C19 C20 -0.6(5) . . . . ? C17 C18 C19 C20 178.5(3) . . . . ? C18 C19 C20 C21 0.7(6) . . . . ? C19 C20 C21 C22 -0.1(7) . . . . ? C20 C21 C22 C23 -0.7(7) . . . . ? C21 C22 C23 N2 -178.1(4) . . . . ? C21 C22 C23 C18 0.8(6) . . . . ? C19 C18 C23 N2 178.9(3) . . . . ? C17 C18 C23 N2 -0.5(4) . . . . ? C19 C18 C23 C22 -0.1(5) . . . . ? C17 C18 C23 C22 -179.5(3) . . . . ? C16 C17 C24 N2 -179.3(3) . . . . ? C18 C17 C24 N2 -0.1(4) . . . . ? C16 C17 C24 C1 0.9(4) . . . . ? C18 C17 C24 C1 -179.9(3) . . . . ? N1 C1 C24 N2 -1.9(6) . . . . ? C8 C1 C24 N2 178.9(3) . . . . ? N1 C1 C24 C17 177.8(3) . . . . ? C8 C1 C24 C17 -1.3(4) . . . . ? N5 C25 C26 C27 -174.9(4) . . . . ? C25 C26 C27 C28 -177.2(5) . . . . ? N5 C29 C30 C31 170.3(4) . . . . ? C29 C30 C31 C32 -78.7(7) . . . . ? N5 C33 C34 C35 163.1(5) . . . . ? C33 C34 C35 C36 -176.0(6) . . . . ? N5 C37 C38 C39 156.7(6) . . . . ? C37 C38 C39 C40 -164.9(10) . . . . ? C8 C1 N1 C2 0.3(4) . . . . ? C24 C1 N1 C2 -178.9(3) . . . . ? C3 C2 N1 C1 179.3(3) . . . . ? C7 C2 N1 C1 -1.0(3) . . . . ? C17 C24 N2 C23 -0.2(4) . . . . ? C1 C24 N2 C23 179.6(3) . . . . ? C22 C23 N2 C24 179.3(4) . . . . ? C18 C23 N2 C24 0.4(4) . . . . ? C17 C16 N3 C15 -179.9(3) . . . . ? C9 C16 N3 C15 0.6(4) . . . . ? C10 C15 N3 C16 -0.3(4) . . . . ? C14 C15 N3 C16 -179.5(3) . . . . ? C8 C9 N4 C10 179.9(3) . . . . ? C16 C9 N4 C10 -0.3(4) . . . . ? C15 C10 N4 C9 0.6(4) . . . . ? C11 C10 N4 C9 -178.7(3) . . . . ? C38 C37 N5 C33 -60.9(5) . . . . ? C38 C37 N5 C25 58.6(5) . . . . ? C38 C37 N5 C29 179.5(4) . . . . ? C34 C33 N5 C37 -59.5(5) . . . . ? C34 C33 N5 C25 179.5(4) . . . . ? C34 C33 N5 C29 59.4(5) . . . . ? C26 C25 N5 C37 60.4(4) . . . . ? C26 C25 N5 C33 -178.7(4) . . . . ? C26 C25 N5 C29 -59.1(5) . . . . ? C30 C29 N5 C37 174.3(4) . . . . ? C30 C29 N5 C33 53.9(5) . . . . ? C30 C29 N5 C25 -64.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.739 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.047 # ---------------Attachment 'DIPZ-Br.CIF' data_r81222a _database_code_depnum_ccdc_archive 'CCDC 748206' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DIPZ+Br _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H50 Br N5' _chemical_formula_weight 680.76 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.188(3) _cell_length_b 14.799(3) _cell_length_c 18.574(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3625.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 5684 _cell_measurement_theta_min 1.759 _cell_measurement_theta_max 27.136 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 1.168 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8179 _exptl_absorpt_correction_T_max 0.8925 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22179 _diffrn_reflns_av_R_equivalents 0.1426 _diffrn_reflns_av_sigmaI/netI 0.1608 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6360 _reflns_number_gt 3884 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Restraints are made to the disorder of tetrabutylammonium cation, including the bond lengths of N-C(1.50) and(1.54 and 2.50) bonds. These retraints could make them close to the theoretical lengths of these bonds. ; _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^)+(0.0686P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0035(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.019(15) _refine_ls_number_reflns 6360 _refine_ls_number_parameters 515 _refine_ls_number_restraints 312 _refine_ls_R_factor_all 0.1193 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.1833 _refine_ls_wR_factor_gt 0.1594 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.998 _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 Br1 Br 0.40653(6) 0.37729(6) 0.72306(4) 0.0608(3) Uani 1 1 d . . . N1 N 0.3434(4) 0.6721(4) 0.2350(3) 0.0439(15) Uani 1 1 d . . . H1 H 0.2792 0.6818 0.2334 0.053 Uiso 1 1 calc R . . N2 N 0.6716(4) 0.5803(4) 0.1748(3) 0.0337(13) Uani 1 1 d . . . N3 N 0.5981(5) 0.4863(3) 0.0508(3) 0.0390(13) Uani 1 1 d . . . N4 N 0.2644(5) 0.5577(4) 0.1056(3) 0.0434(15) Uani 1 1 d . . . H4 H 0.2112 0.5808 0.1251 0.052 Uiso 1 1 calc R . . C1 C 0.4103(6) 0.7055(4) 0.2870(3) 0.0408(16) Uani 1 1 d . . . C2 C 0.3929(7) 0.7600(5) 0.3464(4) 0.055(2) Uani 1 1 d . . . H2 H 0.3281 0.7816 0.3563 0.066 Uiso 1 1 calc R . . C3 C 0.4732(7) 0.7818(5) 0.3908(4) 0.051(2) Uani 1 1 d . . . H3 H 0.4627 0.8189 0.4305 0.062 Uiso 1 1 calc R . . C4 C 0.5703(6) 0.7483(5) 0.3764(4) 0.0472(19) Uani 1 1 d . . . H4A H 0.6230 0.7614 0.4079 0.057 Uiso 1 1 calc R . . C5 C 0.5899(7) 0.6952(4) 0.3153(3) 0.0457(18) Uani 1 1 d . . . H5 H 0.6550 0.6742 0.3056 0.055 Uiso 1 1 calc R . . C6 C 0.5093(5) 0.6749(4) 0.2695(3) 0.0368(16) Uani 1 1 d . . . C7 C 0.4992(5) 0.6221(5) 0.2047(3) 0.0404(16) Uani 1 1 d . . . C8 C 0.5726(5) 0.5763(4) 0.1591(3) 0.0306(15) Uani 1 1 d . . . C9 C 0.7362(5) 0.5354(4) 0.1281(3) 0.0368(16) Uani 1 1 d . . . C10 C 0.8411(6) 0.5359(5) 0.1428(4) 0.0464(19) Uani 1 1 d . . . H10 H 0.8656 0.5640 0.1840 0.056 Uiso 1 1 calc R . . C11 C 0.9060(7) 0.4955(5) 0.0968(4) 0.057(2) Uani 1 1 d . . . H11 H 0.9752 0.4971 0.1063 0.068 Uiso 1 1 calc R . . C12 C 0.8710(6) 0.4512(6) 0.0352(4) 0.060(2) Uani 1 1 d . . . H12 H 0.9173 0.4243 0.0041 0.072 Uiso 1 1 calc R . . C13 C 0.7701(6) 0.4469(5) 0.0198(4) 0.051(2) Uani 1 1 d . . . H13 H 0.7477 0.4158 -0.0207 0.061 Uiso 1 1 calc R . . C14 C 0.6992(6) 0.4900(5) 0.0660(3) 0.0414(17) Uani 1 1 d . . . C15 C 0.5346(5) 0.5284(4) 0.0963(3) 0.0360(17) Uani 1 1 d . . . C16 C 0.4278(6) 0.5242(4) 0.0842(3) 0.0380(17) Uani 1 1 d . . . C17 C 0.3679(6) 0.4775(5) 0.0307(3) 0.0428(18) Uani 1 1 d . . . C18 C 0.3871(7) 0.4204(5) -0.0277(3) 0.051(2) Uani 1 1 d . . . H18 H 0.4530 0.4041 -0.0399 0.061 Uiso 1 1 calc R . . C19 C 0.3043(6) 0.3885(5) -0.0670(3) 0.052(2) Uani 1 1 d . . . H19 H 0.3163 0.3501 -0.1058 0.063 Uiso 1 1 calc R . . C20 C 0.2043(7) 0.4116(5) -0.0508(4) 0.055(2) Uani 1 1 d . . . H20 H 0.1516 0.3880 -0.0783 0.066 Uiso 1 1 calc R . . C21 C 0.1833(6) 0.4685(6) 0.0049(4) 0.053(2) Uani 1 1 d . . . H21 H 0.1171 0.4859 0.0152 0.064 Uiso 1 1 calc R . . C22 C 0.2658(5) 0.4999(5) 0.0464(3) 0.0382(16) Uani 1 1 d . . . C23 C 0.3623(5) 0.5713(5) 0.1272(3) 0.0376(17) Uani 1 1 d . . . C24 C 0.3983(5) 0.6211(5) 0.1869(3) 0.0376(14) Uani 1 1 d . . . N5 N 0.6280(5) 0.1595(4) 0.6728(3) 0.072(2) Uani 1 1 d D . . C29 C 0.5440(6) 0.0930(5) 0.6631(4) 0.070(2) Uani 1 1 d DU A . H29A H 0.5551 0.0437 0.6966 0.084 Uiso 1 1 calc R . . H29B H 0.5493 0.0682 0.6149 0.084 Uiso 1 1 calc R . . C30 C 0.4364(6) 0.1263(6) 0.6733(4) 0.074(2) Uani 1 1 d DU . . H30A H 0.4230 0.1772 0.6417 0.089 Uiso 1 1 calc R A . H30B H 0.4260 0.1456 0.7227 0.089 Uiso 1 1 calc R . . C31 C 0.3645(6) 0.0462(7) 0.6548(5) 0.088(3) Uani 1 1 d DU A . H31A H 0.3701 0.0315 0.6041 0.106 Uiso 1 1 calc R . . H31B H 0.3837 -0.0067 0.6825 0.106 Uiso 1 1 calc R . . C32 C 0.2572(7) 0.0722(8) 0.6722(6) 0.124(4) Uani 1 1 d DU . . H32A H 0.2126 0.0233 0.6599 0.149 Uiso 1 1 calc R A . H32B H 0.2388 0.1249 0.6451 0.149 Uiso 1 1 calc R . . H32C H 0.2516 0.0850 0.7227 0.149 Uiso 1 1 calc R . . C25 C 0.6238(8) 0.2316(5) 0.6156(3) 0.071(2) Uani 0.50 1 d PDU A 1 H25A H 0.6743 0.2776 0.6256 0.085 Uiso 0.50 1 calc PR A 1 H25B H 0.5576 0.2601 0.6159 0.085 Uiso 0.50 1 calc PR A 1 C26 C 0.6440(14) 0.1896(9) 0.5413(6) 0.059(3) Uani 0.50 1 d PDU A 1 H26A H 0.5843 0.1583 0.5237 0.071 Uiso 0.50 1 calc PR A 1 H26B H 0.7000 0.1472 0.5435 0.071 Uiso 0.50 1 calc PR A 1 C27 C 0.6703(11) 0.2700(9) 0.4921(7) 0.048(3) Uani 0.50 1 d PDU A 1 H27A H 0.6334 0.3234 0.5071 0.058 Uiso 0.50 1 calc PR A 1 H27B H 0.6522 0.2564 0.4427 0.058 Uiso 0.50 1 calc PR A 1 C28 C 0.7855(12) 0.2860(13) 0.4985(11) 0.097(6) Uani 0.50 1 d PDU A 1 H28A H 0.8048 0.3355 0.4680 0.116 Uiso 0.50 1 calc PR A 1 H28B H 0.8211 0.2325 0.4839 0.116 Uiso 0.50 1 calc PR A 1 H28C H 0.8023 0.3000 0.5475 0.116 Uiso 0.50 1 calc PR A 1 C25' C 0.6238(8) 0.2316(5) 0.6156(3) 0.071(2) Uani 0.50 1 d PDU A 2 H25C H 0.6865 0.2654 0.6199 0.085 Uiso 0.50 1 calc PR A 2 H25D H 0.5699 0.2724 0.6298 0.085 Uiso 0.50 1 calc PR A 2 C26' C 0.6087(15) 0.2143(10) 0.5339(5) 0.067(4) Uani 0.50 1 d PDU A 2 H26C H 0.6724 0.1905 0.5159 0.080 Uiso 0.50 1 calc PR A 2 H26D H 0.5594 0.1660 0.5297 0.080 Uiso 0.50 1 calc PR A 2 C27' C 0.5757(13) 0.2883(10) 0.4811(6) 0.067(4) Uani 0.50 1 d PDU A 2 H27C H 0.6118 0.3439 0.4918 0.080 Uiso 0.50 1 calc PR A 2 H27D H 0.5925 0.2703 0.4324 0.080 Uiso 0.50 1 calc PR A 2 C28' C 0.4628(14) 0.3043(16) 0.4871(12) 0.133(8) Uani 0.50 1 d PDU A 2 H28D H 0.4436 0.3533 0.4561 0.159 Uiso 0.50 1 calc PR A 2 H28E H 0.4459 0.3191 0.5360 0.159 Uiso 0.50 1 calc PR A 2 H28F H 0.4271 0.2506 0.4730 0.159 Uiso 0.50 1 calc PR A 2 C33 C 0.6121(16) 0.1964(9) 0.7488(5) 0.041(4) Uani 0.50 1 d PDU A 3 H33A H 0.5540 0.2364 0.7455 0.049 Uiso 0.50 1 calc PR A 3 H33B H 0.6702 0.2348 0.7582 0.049 Uiso 0.50 1 calc PR A 3 C34 C 0.5962(12) 0.1413(7) 0.8181(5) 0.041(3) Uani 0.50 1 d PDU A 3 H34A H 0.5452 0.0954 0.8092 0.049 Uiso 0.50 1 calc PR A 3 H34B H 0.6590 0.1106 0.8301 0.049 Uiso 0.50 1 calc PR A 3 C35 C 0.5635(10) 0.1977(8) 0.8819(6) 0.033(3) Uani 0.50 1 d PDU A 3 H35A H 0.5536 0.1581 0.9230 0.039 Uiso 0.50 1 calc PR A 3 H35B H 0.4986 0.2253 0.8709 0.039 Uiso 0.50 1 calc PR A 3 C36 C 0.6380(10) 0.2721(8) 0.9031(7) 0.039(3) Uani 0.50 1 d PDU A 3 H36A H 0.6117 0.3050 0.9435 0.047 Uiso 0.50 1 calc PR A 3 H36B H 0.6474 0.3125 0.8632 0.047 Uiso 0.50 1 calc PR A 3 H36C H 0.7020 0.2455 0.9158 0.047 Uiso 0.50 1 calc PR A 3 C33' C 0.6289(19) 0.2215(9) 0.7365(6) 0.059(5) Uani 0.50 1 d PDU A 4 H33C H 0.5632 0.2498 0.7429 0.070 Uiso 0.50 1 calc PR A 4 H33D H 0.6796 0.2684 0.7305 0.070 Uiso 0.50 1 calc PR A 4 C34' C 0.6548(14) 0.1610(10) 0.8012(7) 0.067(4) Uani 0.50 1 d PDU A 4 H34C H 0.7225 0.1362 0.7960 0.081 Uiso 0.50 1 calc PR A 4 H34D H 0.6069 0.1115 0.8047 0.081 Uiso 0.50 1 calc PR A 4 C35' C 0.6486(12) 0.2213(12) 0.8688(7) 0.075(4) Uani 0.50 1 d PDU A 4 H35C H 0.6777 0.1903 0.9099 0.090 Uiso 0.50 1 calc PR A 4 H35D H 0.6858 0.2770 0.8611 0.090 Uiso 0.50 1 calc PR A 4 C36' C 0.5366(13) 0.2418(13) 0.8825(9) 0.070(5) Uani 0.50 1 d PDU A 4 H36D H 0.5303 0.2784 0.9249 0.084 Uiso 0.50 1 calc PR A 4 H36E H 0.5003 0.1862 0.8892 0.084 Uiso 0.50 1 calc PR A 4 H36F H 0.5090 0.2736 0.8420 0.084 Uiso 0.50 1 calc PR A 4 C37 C 0.7128(7) 0.0881(7) 0.6827(7) 0.039(3) Uani 0.50 1 d PDU A 5 H37A H 0.6935 0.0471 0.7210 0.047 Uiso 0.50 1 calc PR A 5 H37B H 0.7188 0.0531 0.6387 0.047 Uiso 0.50 1 calc PR A 5 C38 C 0.8170(7) 0.1294(8) 0.7007(6) 0.037(3) Uani 0.50 1 d PDU A 5 H38A H 0.8270 0.1842 0.6729 0.044 Uiso 0.50 1 calc PR A 5 H38B H 0.8196 0.1450 0.7514 0.044 Uiso 0.50 1 calc PR A 5 C39 C 0.9017(9) 0.0615(11) 0.6832(11) 0.044(4) Uani 0.50 1 d PDU A 5 H39A H 0.9057 0.0531 0.6314 0.053 Uiso 0.50 1 calc PR A 5 H39B H 0.8858 0.0036 0.7049 0.053 Uiso 0.50 1 calc PR A 5 C40 C 1.0047(9) 0.0952(11) 0.7116(10) 0.042(4) Uani 0.50 1 d PDU A 5 H40A H 1.0565 0.0522 0.6997 0.051 Uiso 0.50 1 calc PR A 5 H40B H 1.0013 0.1020 0.7630 0.051 Uiso 0.50 1 calc PR A 5 H40C H 1.0206 0.1524 0.6900 0.051 Uiso 0.50 1 calc PR A 5 C37' C 0.7319(9) 0.1221(13) 0.6518(11) 0.082(5) Uani 0.50 1 d PDU A 6 H37C H 0.7246 0.0932 0.6053 0.099 Uiso 0.50 1 calc PR A 6 H37D H 0.7487 0.0750 0.6861 0.099 Uiso 0.50 1 calc PR A 6 C38' C 0.8238(13) 0.1854(11) 0.6470(11) 0.091(5) Uani 0.50 1 d PDU A 6 H38C H 0.8292 0.2201 0.6912 0.110 Uiso 0.50 1 calc PR A 6 H38D H 0.8143 0.2274 0.6075 0.110 Uiso 0.50 1 calc PR A 6 C39' C 0.9227(13) 0.1316(14) 0.6352(8) 0.127(9) Uani 0.50 1 d PD A 6 H39C H 0.9157 0.0930 0.5932 0.153 Uiso 0.50 1 calc PR A 6 H39D H 0.9785 0.1730 0.6267 0.153 Uiso 0.50 1 calc PR A 6 C40' C 0.944(2) 0.0745(14) 0.7012(10) 0.079(8) Uani 0.50 1 d PD A 6 H40D H 1.0057 0.0407 0.6938 0.095 Uiso 0.50 1 calc PR A 6 H40E H 0.8891 0.0336 0.7093 0.095 Uiso 0.50 1 calc PR A 6 H40F H 0.9523 0.1131 0.7424 0.095 Uiso 0.50 1 calc PR A 6 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 Br1 0.0341(4) 0.0818(5) 0.0665(5) 0.0113(4) -0.0013(4) 0.0062(5) N1 0.033(3) 0.051(3) 0.048(3) -0.010(3) -0.002(3) 0.009(3) N2 0.024(3) 0.046(3) 0.032(3) 0.005(2) 0.001(3) -0.004(3) N3 0.034(3) 0.051(3) 0.031(3) 0.006(2) -0.004(3) -0.003(3) N4 0.027(4) 0.068(4) 0.035(3) 0.003(3) -0.001(3) -0.008(3) C1 0.042(4) 0.049(4) 0.032(3) -0.005(3) -0.009(4) 0.002(4) C2 0.060(6) 0.051(4) 0.054(4) -0.008(3) 0.007(5) 0.005(4) C3 0.054(6) 0.056(5) 0.044(4) -0.009(3) -0.006(4) 0.000(4) C4 0.044(5) 0.052(4) 0.045(4) -0.004(3) -0.009(4) -0.006(4) C5 0.046(5) 0.053(4) 0.038(4) 0.005(3) 0.006(4) 0.002(4) C6 0.048(5) 0.033(3) 0.030(3) 0.000(3) -0.009(4) -0.002(3) C7 0.042(4) 0.044(3) 0.035(4) -0.006(3) -0.002(3) -0.004(4) C8 0.033(4) 0.032(3) 0.027(3) 0.006(2) -0.006(3) -0.001(3) C9 0.029(4) 0.047(4) 0.034(4) 0.011(3) 0.000(3) 0.001(3) C10 0.039(5) 0.060(5) 0.040(4) 0.005(3) -0.002(4) 0.004(4) C11 0.029(4) 0.079(5) 0.061(5) 0.003(4) 0.000(5) 0.009(5) C12 0.035(5) 0.089(6) 0.056(5) -0.015(4) -0.002(4) 0.020(5) C13 0.048(5) 0.070(5) 0.034(4) -0.006(3) 0.007(4) 0.003(4) C14 0.040(5) 0.052(4) 0.032(4) 0.007(3) 0.006(4) 0.011(4) C15 0.037(5) 0.044(4) 0.027(3) 0.008(3) 0.002(3) -0.002(3) C16 0.040(5) 0.046(4) 0.028(3) 0.008(3) -0.007(3) -0.008(3) C17 0.037(4) 0.057(4) 0.034(4) 0.008(3) 0.005(4) -0.012(4) C18 0.063(6) 0.062(4) 0.029(3) 0.000(3) 0.011(4) -0.008(4) C19 0.066(6) 0.063(5) 0.028(3) -0.004(3) -0.004(4) -0.030(5) C20 0.057(6) 0.079(5) 0.029(4) -0.006(3) 0.003(4) -0.028(5) C21 0.043(5) 0.085(6) 0.032(4) 0.012(4) 0.001(4) -0.019(4) C22 0.025(4) 0.063(4) 0.027(3) 0.005(3) -0.005(3) -0.011(4) C23 0.024(4) 0.054(4) 0.035(4) 0.008(3) -0.001(3) -0.003(3) C24 0.034(4) 0.048(3) 0.031(3) 0.009(3) -0.001(3) -0.001(4) N5 0.053(5) 0.090(5) 0.071(5) -0.047(4) -0.011(4) 0.009(4) C29 0.075(5) 0.084(5) 0.052(4) -0.003(4) -0.006(4) -0.002(4) C30 0.073(5) 0.087(5) 0.063(4) -0.019(4) -0.007(4) -0.010(4) C31 0.083(6) 0.105(5) 0.078(5) -0.029(4) -0.011(5) 0.008(5) C32 0.120(8) 0.135(7) 0.118(7) -0.011(6) -0.004(7) -0.007(7) C25 0.075(5) 0.072(4) 0.066(4) -0.018(3) 0.016(4) -0.011(4) C26 0.065(6) 0.060(6) 0.053(6) -0.013(5) 0.014(5) -0.007(5) C27 0.051(6) 0.051(6) 0.043(6) -0.005(5) 0.005(6) 0.007(6) C28 0.110(10) 0.096(9) 0.084(8) 0.008(7) 0.001(8) 0.003(8) C25' 0.075(5) 0.072(4) 0.066(4) -0.018(3) 0.016(4) -0.011(4) C26' 0.079(7) 0.059(6) 0.063(6) -0.022(5) 0.010(6) 0.001(6) C27' 0.088(7) 0.061(6) 0.051(6) -0.016(5) 0.007(6) -0.009(6) C28' 0.155(11) 0.129(11) 0.114(10) -0.008(8) -0.008(9) 0.005(9) C33 0.048(7) 0.039(6) 0.035(6) -0.005(5) -0.001(6) 0.000(6) C34 0.041(5) 0.045(5) 0.037(5) -0.004(4) 0.005(5) -0.009(5) C35 0.026(6) 0.043(6) 0.029(5) 0.001(5) 0.003(5) -0.007(5) C36 0.031(6) 0.049(6) 0.036(6) -0.020(5) 0.003(6) 0.000(5) C33' 0.072(8) 0.047(7) 0.057(7) -0.012(6) 0.005(6) -0.001(6) C34' 0.077(7) 0.064(6) 0.061(6) -0.005(5) -0.001(6) 0.003(6) C35' 0.083(7) 0.075(7) 0.068(7) 0.008(6) -0.002(7) 0.005(6) C36' 0.078(9) 0.071(8) 0.062(8) 0.011(7) 0.004(7) 0.005(8) C37 0.044(6) 0.046(5) 0.028(5) 0.001(5) -0.004(5) -0.002(5) C38 0.044(6) 0.041(5) 0.025(5) 0.005(4) -0.005(4) -0.006(5) C39 0.049(7) 0.056(6) 0.028(6) 0.010(5) -0.016(6) 0.000(6) C40 0.046(8) 0.042(6) 0.039(7) 0.002(5) -0.006(7) 0.000(6) C37' 0.071(8) 0.085(8) 0.091(8) -0.022(7) 0.009(7) 0.000(7) C38' 0.081(8) 0.092(8) 0.100(8) -0.019(7) 0.007(7) 0.007(7) C39' 0.19(3) 0.126(19) 0.064(12) -0.025(13) 0.005(17) -0.01(2) C40' 0.12(3) 0.079(17) 0.042(16) 0.006(10) -0.005(18) 0.032(19) _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 N1 C24 1.375(8) . ? N1 C1 1.398(8) . ? N1 H1 0.8600 . ? N2 C8 1.340(8) . ? N2 C9 1.386(8) . ? N3 C15 1.343(8) . ? N3 C14 1.364(9) . ? N4 C23 1.368(8) . ? N4 C22 1.392(8) . ? N4 H4 0.8600 . ? C1 C2 1.386(9) . ? C1 C6 1.419(10) . ? C2 C3 1.380(11) . ? C2 H2 0.9300 . ? C3 C4 1.400(10) . ? C3 H3 0.9300 . ? C4 C5 1.404(9) . ? C4 H4A 0.9300 . ? C5 C6 1.394(10) . ? C5 H5 0.9300 . ? C6 C7 1.440(8) . ? C7 C24 1.372(9) . ? C7 C8 1.454(9) . ? C8 C15 1.455(8) . ? C9 C10 1.410(9) . ? C9 C14 1.422(9) . ? C10 C11 1.348(10) . ? C10 H10 0.9300 . ? C11 C12 1.397(10) . ? C11 H11 0.9300 . ? C12 C13 1.363(10) . ? C12 H12 0.9300 . ? C13 C14 1.419(9) . ? C13 H13 0.9300 . ? C15 C16 1.428(9) . ? C16 C23 1.367(9) . ? C16 C17 1.446(9) . ? C17 C18 1.397(9) . ? C17 C22 1.417(9) . ? C18 C19 1.397(10) . ? C18 H18 0.9300 . ? C19 C20 1.395(10) . ? C19 H19 0.9300 . ? C20 C21 1.363(10) . ? C20 H20 0.9300 . ? C21 C22 1.413(10) . ? C21 H21 0.9300 . ? C23 C24 1.414(9) . ? N5 C29 1.492(7) . ? N5 C33' 1.499(9) . ? N5 C25 1.506(6) . ? N5 C37' 1.529(9) . ? N5 C33 1.529(8) . ? N5 C37 1.550(8) . ? C29 C30 1.514(8) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.557(8) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.501(8) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C25 C26 1.537(9) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.538(9) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.542(10) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C26' C27' 1.533(9) . ? C26' H26C 0.9700 . ? C26' H26D 0.9700 . ? C27' C28' 1.512(10) . ? C27' H27C 0.9700 . ? C27' H27D 0.9700 . ? C28' H28D 0.9600 . ? C28' H28E 0.9600 . ? C28' H28F 0.9600 . ? C33 C34 1.539(9) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.513(9) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.527(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C33' C34' 1.536(10) . ? C33' H33C 0.9700 . ? C33' H33D 0.9700 . ? C34' C35' 1.542(9) . ? C34' H34C 0.9700 . ? C34' H34D 0.9700 . ? C35' C36' 1.529(10) . ? C35' H35C 0.9700 . ? C35' H35D 0.9700 . ? C36' H36D 0.9600 . ? C36' H36E 0.9600 . ? C36' H36F 0.9600 . ? C37 C38 1.541(9) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.537(10) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.541(10) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C37' C38' 1.534(10) . ? C37' H37C 0.9700 . ? C37' H37D 0.9700 . ? C38' C39' 1.543(10) . ? C38' H38C 0.9700 . ? C38' H38D 0.9700 . ? C39' C40' 1.517(10) . ? C39' H39C 0.9700 . ? C39' H39D 0.9700 . ? C40' H40D 0.9600 . ? C40' H40E 0.9600 . ? C40' H40F 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 C24 N1 C1 108.1(6) . . ? C24 N1 H1 125.9 . . ? C1 N1 H1 125.9 . . ? C8 N2 C9 116.2(5) . . ? C15 N3 C14 117.5(6) . . ? C23 N4 C22 108.0(6) . . ? C23 N4 H4 126.0 . . ? C22 N4 H4 126.0 . . ? C2 C1 N1 130.6(7) . . ? C2 C1 C6 121.4(7) . . ? N1 C1 C6 108.0(6) . . ? C3 C2 C1 118.9(8) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 120.4(7) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 121.4(7) . . ? C5 C4 H4A 119.3 . . ? C3 C4 H4A 119.3 . . ? C6 C5 C4 118.2(7) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C5 C6 C1 119.6(6) . . ? C5 C6 C7 134.1(7) . . ? C1 C6 C7 106.2(6) . . ? C24 C7 C8 120.0(6) . . ? C24 C7 C6 107.3(6) . . ? C8 C7 C6 132.7(6) . . ? N2 C8 C7 120.1(6) . . ? N2 C8 C15 122.1(6) . . ? C7 C8 C15 117.8(6) . . ? N2 C9 C10 118.7(6) . . ? N2 C9 C14 121.6(6) . . ? C10 C9 C14 119.7(7) . . ? C11 C10 C9 119.8(7) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 121.1(8) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 121.1(8) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 119.7(7) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? N3 C14 C13 120.0(6) . . ? N3 C14 C9 121.5(6) . . ? C13 C14 C9 118.5(7) . . ? N3 C15 C16 119.8(6) . . ? N3 C15 C8 121.1(6) . . ? C16 C15 C8 119.1(6) . . ? C23 C16 C15 120.6(6) . . ? C23 C16 C17 107.5(6) . . ? C15 C16 C17 131.9(7) . . ? C18 C17 C22 118.3(7) . . ? C18 C17 C16 136.3(7) . . ? C22 C17 C16 105.4(6) . . ? C19 C18 C17 117.9(7) . . ? C19 C18 H18 121.0 . . ? C17 C18 H18 121.0 . . ? C18 C19 C20 122.9(7) . . ? C18 C19 H19 118.5 . . ? C20 C19 H19 118.5 . . ? C21 C20 C19 120.5(7) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 117.5(8) . . ? C20 C21 H21 121.3 . . ? C22 C21 H21 121.3 . . ? N4 C22 C21 128.5(7) . . ? N4 C22 C17 108.7(6) . . ? C21 C22 C17 122.8(6) . . ? C16 C23 N4 110.5(6) . . ? C16 C23 C24 120.8(6) . . ? N4 C23 C24 128.6(7) . . ? C7 C24 N1 110.3(6) . . ? C7 C24 C23 121.4(6) . . ? N1 C24 C23 128.3(6) . . ? C29 N5 C33' 120.4(11) . . ? C29 N5 C25 110.8(6) . . ? C33' N5 C25 97.1(7) . . ? C29 N5 C37' 113.4(8) . . ? C33' N5 C37' 114.5(13) . . ? C25 N5 C37' 96.3(10) . . ? C29 N5 C33 104.2(8) . . ? C33' N5 C33 18.6(9) . . ? C25 N5 C33 113.2(7) . . ? C37' N5 C33 119.1(12) . . ? C29 N5 C37 95.8(6) . . ? C33' N5 C37 108.5(10) . . ? C25 N5 C37 126.3(8) . . ? C37' N5 C37 30.2(8) . . ? C33 N5 C37 103.4(10) . . ? N5 C29 C30 117.7(7) . . ? N5 C29 H29A 107.9 . . ? C30 C29 H29A 107.9 . . ? N5 C29 H29B 107.9 . . ? C30 C29 H29B 107.9 . . ? H29A C29 H29B 107.2 . . ? C29 C30 C31 107.1(6) . . ? C29 C30 H30A 110.3 . . ? C31 C30 H30A 110.3 . . ? C29 C30 H30B 110.3 . . ? C31 C30 H30B 110.3 . . ? H30A C30 H30B 108.5 . . ? C32 C31 C30 109.3(7) . . ? C32 C31 H31A 109.8 . . ? C30 C31 H31A 109.8 . . ? C32 C31 H31B 109.8 . . ? C30 C31 H31B 109.8 . . ? H31A C31 H31B 108.3 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N5 C25 C26 109.9(7) . . ? N5 C25 H25A 109.7 . . ? C26 C25 H25A 109.7 . . ? N5 C25 H25B 109.7 . . ? C26 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? C25 C26 C27 105.1(9) . . ? C25 C26 H26A 110.7 . . ? C27 C26 H26A 110.7 . . ? C25 C26 H26B 110.7 . . ? C27 C26 H26B 110.7 . . ? H26A C26 H26B 108.8 . . ? C26 C27 C28 107.2(11) . . ? C26 C27 H27A 110.3 . . ? C28 C27 H27A 110.3 . . ? C26 C27 H27B 110.3 . . ? C28 C27 H27B 110.3 . . ? H27A C27 H27B 108.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27' C26' H26C 106.6 . . ? C27' C26' H26D 106.6 . . ? H26C C26' H26D 106.6 . . ? C28' C27' C26' 110.1(12) . . ? C28' C27' H27C 109.6 . . ? C26' C27' H27C 109.6 . . ? C28' C27' H27D 109.6 . . ? C26' C27' H27D 109.6 . . ? H27C C27' H27D 108.1 . . ? C27' C28' H28D 109.5 . . ? C27' C28' H28E 109.5 . . ? H28D C28' H28E 109.5 . . ? C27' C28' H28F 109.5 . . ? H28D C28' H28F 109.5 . . ? H28E C28' H28F 109.5 . . ? N5 C33 C34 127.1(10) . . ? N5 C33 H33A 105.5 . . ? C34 C33 H33A 105.5 . . ? N5 C33 H33B 105.5 . . ? C34 C33 H33B 105.5 . . ? H33A C33 H33B 106.1 . . ? C35 C34 C33 113.7(8) . . ? C35 C34 H34A 108.8 . . ? C33 C34 H34A 108.8 . . ? C35 C34 H34B 108.8 . . ? C33 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? C34 C35 C36 114.6(9) . . ? C34 C35 H35A 108.6 . . ? C36 C35 H35A 108.6 . . ? C34 C35 H35B 108.6 . . ? C36 C35 H35B 108.6 . . ? H35A C35 H35B 107.6 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N5 C33' C34' 105.2(10) . . ? N5 C33' H33C 110.7 . . ? C34' C33' H33C 110.7 . . ? N5 C33' H33D 110.7 . . ? C34' C33' H33D 110.7 . . ? H33C C33' H33D 108.8 . . ? C33' C34' C35' 106.7(9) . . ? C33' C34' H34C 110.4 . . ? C35' C34' H34C 110.4 . . ? C33' C34' H34D 110.4 . . ? C35' C34' H34D 110.4 . . ? H34C C34' H34D 108.6 . . ? C36' C35' C34' 107.6(11) . . ? C36' C35' H35C 110.2 . . ? C34' C35' H35C 110.2 . . ? C36' C35' H35D 110.2 . . ? C34' C35' H35D 110.2 . . ? H35C C35' H35D 108.5 . . ? C35' C36' H36D 109.5 . . ? C35' C36' H36E 109.5 . . ? H36D C36' H36E 109.5 . . ? C35' C36' H36F 109.5 . . ? H36D C36' H36F 109.5 . . ? H36E C36' H36F 109.5 . . ? C38 C37 N5 113.6(8) . . ? C38 C37 H37A 108.9 . . ? N5 C37 H37A 108.9 . . ? C38 C37 H37B 108.9 . . ? N5 C37 H37B 108.9 . . ? H37A C37 H37B 107.7 . . ? C39 C38 C37 110.0(8) . . ? C39 C38 H38A 109.7 . . ? C37 C38 H38A 109.7 . . ? C39 C38 H38B 109.7 . . ? C37 C38 H38B 109.7 . . ? H38A C38 H38B 108.2 . . ? C38 C39 C40 110.9(11) . . ? C38 C39 H39A 109.5 . . ? C40 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? C40 C39 H39B 109.5 . . ? H39A C39 H39B 108.1 . . ? 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 . . ? N5 C37' C38' 120.2(14) . . ? N5 C37' H37C 107.3 . . ? C38' C37' H37C 107.3 . . ? N5 C37' H37D 107.3 . . ? C38' C37' H37D 107.3 . . ? H37C C37' H37D 106.9 . . ? C37' C38' C39' 111.2(11) . . ? C37' C38' H38C 109.4 . . ? C39' C38' H38C 109.4 . . ? C37' C38' H38D 109.4 . . ? C39' C38' H38D 109.4 . . ? H38C C38' H38D 108.0 . . ? C40' C39' C38' 109.4(11) . . ? C40' C39' H39C 109.8 . . ? C38' C39' H39C 109.8 . . ? C40' C39' H39D 109.8 . . ? C38' C39' H39D 109.8 . . ? H39C C39' H39D 108.3 . . ? C39' C40' H40D 109.5 . . ? C39' C40' H40E 109.5 . . ? H40D C40' H40E 109.5 . . ? C39' C40' H40F 109.5 . . ? H40D C40' H40F 109.5 . . ? H40E C40' H40F 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 C24 N1 C1 C2 179.8(7) . . . . ? C24 N1 C1 C6 0.8(7) . . . . ? N1 C1 C2 C3 178.5(7) . . . . ? C6 C1 C2 C3 -2.5(10) . . . . ? C1 C2 C3 C4 -0.8(11) . . . . ? C2 C3 C4 C5 2.8(11) . . . . ? C3 C4 C5 C6 -1.3(10) . . . . ? C4 C5 C6 C1 -2.0(9) . . . . ? C4 C5 C6 C7 -178.1(7) . . . . ? C2 C1 C6 C5 4.0(10) . . . . ? N1 C1 C6 C5 -176.8(5) . . . . ? C2 C1 C6 C7 -178.9(6) . . . . ? N1 C1 C6 C7 0.3(7) . . . . ? C5 C6 C7 C24 175.2(7) . . . . ? C1 C6 C7 C24 -1.2(7) . . . . ? C5 C6 C7 C8 -6.3(13) . . . . ? C1 C6 C7 C8 177.2(7) . . . . ? C9 N2 C8 C7 -179.4(5) . . . . ? C9 N2 C8 C15 -0.7(8) . . . . ? C24 C7 C8 N2 177.3(6) . . . . ? C6 C7 C8 N2 -1.0(11) . . . . ? C24 C7 C8 C15 -1.6(9) . . . . ? C6 C7 C8 C15 -179.9(6) . . . . ? C8 N2 C9 C10 -178.8(6) . . . . ? C8 N2 C9 C14 1.8(9) . . . . ? N2 C9 C10 C11 -177.6(7) . . . . ? C14 C9 C10 C11 1.8(10) . . . . ? C9 C10 C11 C12 -1.3(11) . . . . ? C10 C11 C12 C13 -0.5(12) . . . . ? C11 C12 C13 C14 1.7(12) . . . . ? C15 N3 C14 C13 -179.9(6) . . . . ? C15 N3 C14 C9 1.0(9) . . . . ? C12 C13 C14 N3 179.7(7) . . . . ? C12 C13 C14 C9 -1.2(10) . . . . ? N2 C9 C14 N3 -2.0(10) . . . . ? C10 C9 C14 N3 178.6(6) . . . . ? N2 C9 C14 C13 178.8(6) . . . . ? C10 C9 C14 C13 -0.6(10) . . . . ? C14 N3 C15 C16 -177.9(6) . . . . ? C14 N3 C15 C8 0.2(9) . . . . ? N2 C8 C15 N3 -0.3(9) . . . . ? C7 C8 C15 N3 178.5(6) . . . . ? N2 C8 C15 C16 177.8(6) . . . . ? C7 C8 C15 C16 -3.4(8) . . . . ? N3 C15 C16 C23 -175.8(6) . . . . ? C8 C15 C16 C23 6.0(9) . . . . ? N3 C15 C16 C17 3.0(11) . . . . ? C8 C15 C16 C17 -175.1(6) . . . . ? C23 C16 C17 C18 179.4(8) . . . . ? C15 C16 C17 C18 0.4(14) . . . . ? C23 C16 C17 C22 -0.7(8) . . . . ? C15 C16 C17 C22 -179.6(7) . . . . ? C22 C17 C18 C19 -0.2(10) . . . . ? C16 C17 C18 C19 179.8(7) . . . . ? C17 C18 C19 C20 0.4(11) . . . . ? C18 C19 C20 C21 0.8(12) . . . . ? C19 C20 C21 C22 -2.1(11) . . . . ? C23 N4 C22 C21 -178.4(7) . . . . ? C23 N4 C22 C17 -0.4(7) . . . . ? C20 C21 C22 N4 -179.8(7) . . . . ? C20 C21 C22 C17 2.4(11) . . . . ? C18 C17 C22 N4 -179.4(6) . . . . ? C16 C17 C22 N4 0.7(7) . . . . ? C18 C17 C22 C21 -1.3(10) . . . . ? C16 C17 C22 C21 178.8(6) . . . . ? C15 C16 C23 N4 179.6(5) . . . . ? C17 C16 C23 N4 0.5(8) . . . . ? C15 C16 C23 C24 -3.6(10) . . . . ? C17 C16 C23 C24 177.3(6) . . . . ? C22 N4 C23 C16 -0.1(7) . . . . ? C22 N4 C23 C24 -176.6(6) . . . . ? C8 C7 C24 N1 -176.9(5) . . . . ? C6 C7 C24 N1 1.7(7) . . . . ? C8 C7 C24 C23 4.2(10) . . . . ? C6 C7 C24 C23 -177.1(6) . . . . ? C1 N1 C24 C7 -1.6(7) . . . . ? C1 N1 C24 C23 177.2(6) . . . . ? C16 C23 C24 C7 -1.7(10) . . . . ? N4 C23 C24 C7 174.6(7) . . . . ? C16 C23 C24 N1 179.7(6) . . . . ? N4 C23 C24 N1 -4.1(11) . . . . ? C33' N5 C29 C30 46.5(12) . . . . ? C25 N5 C29 C30 -65.6(9) . . . . ? C37' N5 C29 C30 -172.6(11) . . . . ? C33 N5 C29 C30 56.4(11) . . . . ? C37 N5 C29 C30 161.9(8) . . . . ? N5 C29 C30 C31 176.0(7) . . . . ? C29 C30 C31 C32 173.5(9) . . . . ? C29 N5 C25 C26 -65.3(11) . . . . ? C33' N5 C25 C26 168.4(13) . . . . ? C37' N5 C25 C26 52.6(12) . . . . ? C33 N5 C25 C26 178.1(12) . . . . ? C37 N5 C25 C26 49.1(13) . . . . ? N5 C25 C26 C27 -163.1(10) . . . . ? C25 C26 C27 C28 87.7(16) . . . . ? C29 N5 C33 C34 50(2) . . . . ? C33' N5 C33 C34 -158(6) . . . . ? C25 N5 C33 C34 170.4(15) . . . . ? C37' N5 C33 C34 -78(2) . . . . ? C37 N5 C33 C34 -50(2) . . . . ? N5 C33 C34 C35 -169.2(15) . . . . ? C33 C34 C35 C36 -59.6(18) . . . . ? C29 N5 C33' C34' 71.9(18) . . . . ? C25 N5 C33' C34' -168.9(14) . . . . ? C37' N5 C33' C34' -68.6(19) . . . . ? C33 N5 C33' C34' 40(4) . . . . ? C37 N5 C33' C34' -36.7(18) . . . . ? N5 C33' C34' C35' -175.8(14) . . . . ? C33' C34' C35' C36' 71.7(19) . . . . ? C29 N5 C37 C38 -175.5(9) . . . . ? C33' N5 C37 C38 -50.8(14) . . . . ? C25 N5 C37 C38 63.3(12) . . . . ? C37' N5 C37 C38 56.3(17) . . . . ? C33 N5 C37 C38 -69.4(12) . . . . ? N5 C37 C38 C39 -159.8(12) . . . . ? C37 C38 C39 C40 -171.1(16) . . . . ? C29 N5 C37' C38' 170.4(15) . . . . ? C33' N5 C37' C38' -46(2) . . . . ? C25 N5 C37' C38' 54.5(18) . . . . ? C33 N5 C37' C38' -66(2) . . . . ? C37 N5 C37' C38' -131(3) . . . . ? N5 C37' C38' C39' 172.4(14) . . . . ? C37' C38' C39' C40' -66(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.601 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.085 # ---------------Attachment 'DIPZ-BzO.CIF' data_r81120d _database_code_depnum_ccdc_archive 'CCDC 748207' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DIPZ+BzO _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H63 N5 O4' _chemical_formula_weight 810.08 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 13.965(3) _cell_length_b 20.364(4) _cell_length_c 15.881(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.42(3) _cell_angle_gamma 90.00 _cell_volume 4502.8(16) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 4685 _cell_measurement_theta_min 1.629 _cell_measurement_theta_max 27.864 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9880 _exptl_absorpt_correction_T_max 0.9955 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 30429 _diffrn_reflns_av_R_equivalents 0.1483 _diffrn_reflns_av_sigmaI/netI 0.1277 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.02 _reflns_number_total 7943 _reflns_number_gt 3941 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. These restraints are made to refine the bond length of ortho C-C(1.54) in tetrabutylammonium cation, the bond length of N-H(0.90) in indole and the bond length of S-O, fixing them close to the theoretical bond length. ; _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^)+(0.1497P)^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 7943 _refine_ls_number_parameters 613 _refine_ls_number_restraints 266 _refine_ls_R_factor_all 0.1777 _refine_ls_R_factor_gt 0.0969 _refine_ls_wR_factor_ref 0.2948 _refine_ls_wR_factor_gt 0.2470 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.001 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 N1 N 0.3477(2) 0.08411(16) 0.2054(2) 0.0387(9) Uani 1 1 d . . . H1 H 0.2993 0.0940 0.1710 0.046 Uiso 1 1 calc R . . N2 N 0.6578(2) 0.06702(17) 0.3343(2) 0.0363(9) Uani 1 1 d . . . N3 N 0.7318(2) 0.14999(17) 0.2124(2) 0.0394(9) Uani 1 1 d . . . N4 N 0.4255(2) 0.18771(17) 0.0806(2) 0.0390(9) Uani 1 1 d . . . H4 H 0.3650 0.1855 0.0659 0.047 Uiso 1 1 calc R . . C1 C 0.3460(3) 0.0427(2) 0.2745(3) 0.0378(10) Uani 1 1 d . . . C2 C 0.2687(3) 0.0089(2) 0.3049(3) 0.0505(13) Uani 1 1 d . . . H2A H 0.2072 0.0118 0.2783 0.061 Uiso 1 1 calc R . . C3 C 0.2877(3) -0.0287(2) 0.3758(3) 0.0514(13) Uani 1 1 d . . . H3A H 0.2376 -0.0517 0.3975 0.062 Uiso 1 1 calc R . . C4 C 0.3806(3) -0.0337(2) 0.4169(3) 0.0471(12) Uani 1 1 d . . . H4A H 0.3907 -0.0599 0.4647 0.057 Uiso 1 1 calc R . . C5 C 0.4564(3) -0.0001(2) 0.3869(3) 0.0366(10) Uani 1 1 d . . . H5A H 0.5175 -0.0031 0.4144 0.044 Uiso 1 1 calc R . . C6 C 0.4404(3) 0.03837(19) 0.3152(3) 0.0341(10) Uani 1 1 d . . . C7 C 0.4991(3) 0.07917(19) 0.2656(3) 0.0318(10) Uani 1 1 d . . . C8 C 0.6012(3) 0.0936(2) 0.2727(3) 0.0357(10) Uani 1 1 d . . . C9 C 0.7536(3) 0.0813(2) 0.3362(3) 0.0410(11) Uani 1 1 d . . . C10 C 0.8173(3) 0.0555(2) 0.4016(3) 0.0481(13) Uani 1 1 d . . . H10A H 0.7928 0.0307 0.4442 0.058 Uiso 1 1 calc R . . C11 C 0.9135(3) 0.0662(2) 0.4035(4) 0.0550(14) Uani 1 1 d . . . H11A H 0.9543 0.0486 0.4467 0.066 Uiso 1 1 calc R . . C12 C 0.9515(3) 0.1044(3) 0.3392(4) 0.0631(16) Uani 1 1 d . . . H12A H 1.0174 0.1112 0.3401 0.076 Uiso 1 1 calc R . . C13 C 0.8919(3) 0.1314(3) 0.2758(4) 0.0551(14) Uani 1 1 d . . . H13A H 0.9178 0.1562 0.2339 0.066 Uiso 1 1 calc R . . C14 C 0.7906(3) 0.1217(2) 0.2736(3) 0.0425(12) Uani 1 1 d . . . C15 C 0.6389(3) 0.1381(2) 0.2116(3) 0.0351(10) Uani 1 1 d . . . C16 C 0.5709(3) 0.16815(19) 0.1486(3) 0.0331(10) Uani 1 1 d . . . C17 C 0.5834(3) 0.2171(2) 0.0855(3) 0.0356(10) Uani 1 1 d . . . C18 C 0.6613(3) 0.2534(2) 0.0586(3) 0.0438(11) Uani 1 1 d . . . H18A H 0.7231 0.2470 0.0834 0.053 Uiso 1 1 calc R . . C19 C 0.6437(3) 0.2985(2) -0.0053(3) 0.0449(12) Uani 1 1 d . . . H19A H 0.6949 0.3225 -0.0236 0.054 Uiso 1 1 calc R . . C20 C 0.5522(3) 0.3094(2) -0.0435(3) 0.0449(12) Uani 1 1 d . . . H20A H 0.5434 0.3407 -0.0860 0.054 Uiso 1 1 calc R . . C21 C 0.4737(3) 0.2743(2) -0.0189(3) 0.0406(11) Uani 1 1 d . . . H21A H 0.4122 0.2816 -0.0438 0.049 Uiso 1 1 calc R . . C22 C 0.4912(3) 0.2277(2) 0.0449(3) 0.0356(10) Uani 1 1 d . . . C23 C 0.4743(3) 0.15199(19) 0.1441(3) 0.0323(10) Uani 1 1 d . . . C24 C 0.4389(3) 0.1065(2) 0.2014(3) 0.0340(10) Uani 1 1 d . . . N5 N 0.3810(3) 0.1388(2) 0.7769(3) 0.0689(15) Uani 1 1 d . . . C25 C 0.3729(3) 0.1326(3) 0.6815(4) 0.077(2) Uani 1 1 d . A . H25A H 0.4139 0.0968 0.6661 0.092 Uiso 1 1 calc R . . H25B H 0.3975 0.1726 0.6580 0.092 Uiso 1 1 calc R . . C26 C 0.2726(3) 0.1205(3) 0.6408(3) 0.0559(14) Uani 1 1 d . . . H26A H 0.2311 0.1568 0.6539 0.067 Uiso 1 1 calc R A . H26B H 0.2468 0.0807 0.6639 0.067 Uiso 1 1 calc R . . C27 C 0.2735(4) 0.1138(3) 0.5444(4) 0.0710(17) Uani 1 1 d . A . H27A H 0.3072 0.1511 0.5229 0.085 Uiso 1 1 calc R . . H27B H 0.3092 0.0746 0.5319 0.085 Uiso 1 1 calc R . . C28 C 0.1760(4) 0.1099(3) 0.4990(4) 0.0731(17) Uani 1 1 d . . . H28A H 0.1821 0.1049 0.4396 0.110 Uiso 1 1 calc R A . H28B H 0.1411 0.1495 0.5088 0.110 Uiso 1 1 calc R . . H28C H 0.1421 0.0729 0.5195 0.110 Uiso 1 1 calc R . . C29 C 0.3050(3) 0.1836(2) 0.8080(4) 0.0554(14) Uani 1 1 d . A . H29A H 0.3149 0.1867 0.8690 0.067 Uiso 1 1 calc R . . H29B H 0.2427 0.1634 0.7949 0.067 Uiso 1 1 calc R . . C30 C 0.3022(3) 0.2528(3) 0.7718(4) 0.0647(16) Uani 1 1 d . . . H30A H 0.2994 0.2508 0.7106 0.078 Uiso 1 1 calc R A . H30B H 0.3601 0.2763 0.7915 0.078 Uiso 1 1 calc R . . C31 C 0.2144(4) 0.2890(2) 0.7994(4) 0.0662(16) Uani 1 1 d . A . H31A H 0.2127 0.2850 0.8602 0.079 Uiso 1 1 calc R . . H31B H 0.2199 0.3353 0.7862 0.079 Uiso 1 1 calc R . . C32 C 0.1216(4) 0.2626(3) 0.7569(4) 0.0684(16) Uani 1 1 d . . . H32A H 0.0683 0.2859 0.7772 0.103 Uiso 1 1 calc R A . H32B H 0.1159 0.2167 0.7695 0.103 Uiso 1 1 calc R . . H32C H 0.1216 0.2684 0.6969 0.103 Uiso 1 1 calc R . . C33 C 0.3544(9) 0.0622(6) 0.8256(6) 0.043(3) Uani 0.50 1 d PDU A 1 H33A H 0.2932 0.0478 0.7989 0.052 Uiso 0.50 1 calc PR A 1 H33D H 0.4020 0.0311 0.8090 0.052 Uiso 0.50 1 calc PR A 1 C34 C 0.3482(7) 0.0529(4) 0.9221(6) 0.055(3) Uani 0.50 1 d PDU A 1 H34A H 0.4109 0.0603 0.9514 0.066 Uiso 0.50 1 calc PR A 1 H34B H 0.3038 0.0846 0.9427 0.066 Uiso 0.50 1 calc PR A 1 C35 C 0.3142(7) -0.0166(4) 0.9401(5) 0.043(2) Uani 0.50 1 d PDU A 1 H35A H 0.3581 -0.0482 0.9184 0.052 Uiso 0.50 1 calc PR A 1 H35B H 0.2512 -0.0237 0.9114 0.052 Uiso 0.50 1 calc PR A 1 C36 C 0.3091(9) -0.0275(6) 1.0365(6) 0.084(3) Uani 0.50 1 d PDU A 1 H36A H 0.2880 -0.0715 1.0465 0.126 Uiso 0.50 1 calc PR A 1 H36B H 0.2646 0.0032 1.0577 0.126 Uiso 0.50 1 calc PR A 1 H36C H 0.3716 -0.0208 1.0649 0.126 Uiso 0.50 1 calc PR A 1 C33' C 0.3793(9) 0.0801(6) 0.8034(6) 0.048(3) Uani 0.50 1 d PDU A 2 H33B H 0.4280 0.0549 0.7773 0.058 Uiso 0.50 1 calc PR A 2 H33C H 0.3173 0.0609 0.7861 0.058 Uiso 0.50 1 calc PR A 2 C34' C 0.3972(8) 0.0750(4) 0.9013(6) 0.054(3) Uani 0.50 1 d PDU A 2 H34C H 0.4610 0.0909 0.9195 0.065 Uiso 0.50 1 calc PR A 2 H34D H 0.3505 0.1012 0.9286 0.065 Uiso 0.50 1 calc PR A 2 C35' C 0.3873(9) 0.0024(5) 0.9245(7) 0.078(3) Uani 0.50 1 d PDU A 2 H35C H 0.3456 -0.0184 0.8806 0.093 Uiso 0.50 1 calc PR A 2 H35D H 0.4501 -0.0178 0.9236 0.093 Uiso 0.50 1 calc PR A 2 C36' C 0.3506(10) -0.0122(6) 1.0045(8) 0.095(3) Uani 0.50 1 d PDU A 2 H36D H 0.3492 -0.0589 1.0124 0.143 Uiso 0.50 1 calc PR A 2 H36E H 0.2867 0.0051 1.0054 0.143 Uiso 0.50 1 calc PR A 2 H36F H 0.3913 0.0075 1.0490 0.143 Uiso 0.50 1 calc PR A 2 C37 C 0.4789(5) 0.1508(5) 0.8258(8) 0.052(3) Uani 0.50 1 d PDU A 3 H37A H 0.4994 0.1949 0.8127 0.063 Uiso 0.50 1 calc PR A 3 H37B H 0.4692 0.1498 0.8856 0.063 Uiso 0.50 1 calc PR A 3 C38 C 0.5607(5) 0.1042(4) 0.8105(7) 0.057(3) Uani 0.50 1 d PDU A 3 H38A H 0.5618 0.0957 0.7505 0.068 Uiso 0.50 1 calc PR A 3 H38B H 0.5510 0.0627 0.8387 0.068 Uiso 0.50 1 calc PR A 3 C39 C 0.6573(5) 0.1346(5) 0.8447(6) 0.056(2) Uani 0.50 1 d PDU A 3 H39A H 0.6519 0.1518 0.9011 0.067 Uiso 0.50 1 calc PR A 3 H39B H 0.7072 0.1014 0.8474 0.067 Uiso 0.50 1 calc PR A 3 C40 C 0.6829(9) 0.1904(6) 0.7848(9) 0.057(3) Uani 0.50 1 d PDU A 3 H40A H 0.7405 0.2119 0.8074 0.086 Uiso 0.50 1 calc PR A 3 H40B H 0.6312 0.2216 0.7796 0.086 Uiso 0.50 1 calc PR A 3 H40C H 0.6929 0.1725 0.7303 0.086 Uiso 0.50 1 calc PR A 3 C37' C 0.4790(5) 0.1806(5) 0.7888(6) 0.035(2) Uani 0.50 1 d PDU A 4 H37C H 0.4712 0.2202 0.7551 0.042 Uiso 0.50 1 calc PR A 4 H37D H 0.4889 0.1939 0.8475 0.042 Uiso 0.50 1 calc PR A 4 C38' C 0.5690(4) 0.1449(4) 0.7646(6) 0.042(2) Uani 0.50 1 d PDU A 4 H38C H 0.5695 0.1422 0.7036 0.051 Uiso 0.50 1 calc PR A 4 H38D H 0.5710 0.1007 0.7874 0.051 Uiso 0.50 1 calc PR A 4 C39' C 0.6568(5) 0.1853(6) 0.8022(9) 0.052(3) Uani 0.50 1 d PDU A 4 H39C H 0.6509 0.2305 0.7834 0.063 Uiso 0.50 1 calc PR A 4 H39D H 0.6586 0.1849 0.8634 0.063 Uiso 0.50 1 calc PR A 4 C40' C 0.7488(5) 0.1557(5) 0.7737(7) 0.056(2) Uani 0.50 1 d PDU A 4 H40D H 0.8026 0.1820 0.7944 0.085 Uiso 0.50 1 calc PR A 4 H40E H 0.7456 0.1545 0.7131 0.085 Uiso 0.50 1 calc PR A 4 H40F H 0.7564 0.1119 0.7955 0.085 Uiso 0.50 1 calc PR A 4 O1 O 0.1891(2) 0.11259(18) 0.1108(2) 0.0660(11) Uani 1 1 d . . . O2 O 0.2381(2) 0.19126(16) 0.0243(2) 0.0540(9) Uani 1 1 d . . . C41 C 0.1741(3) 0.1575(3) 0.0552(3) 0.0522(13) Uani 1 1 d . . . C42 C 0.0707(3) 0.1705(2) 0.0261(3) 0.0428(11) Uani 1 1 d . . . C43 C 0.0470(3) 0.2119(2) -0.0400(3) 0.0498(13) Uani 1 1 d . . . H43A H 0.0954 0.2323 -0.0674 0.060 Uiso 1 1 calc R . . C44 C -0.0480(3) 0.2239(3) -0.0668(4) 0.0582(15) Uani 1 1 d . . . H44A H -0.0622 0.2514 -0.1128 0.070 Uiso 1 1 calc R . . C45 C -0.1204(3) 0.1964(3) -0.0275(4) 0.0608(15) Uani 1 1 d . . . H45A H -0.1841 0.2040 -0.0465 0.073 Uiso 1 1 calc R . . C46 C -0.0973(3) 0.1568(3) 0.0414(4) 0.0667(16) Uani 1 1 d . . . H46A H -0.1465 0.1393 0.0707 0.080 Uiso 1 1 calc R . . C47 C -0.0027(3) 0.1423(3) 0.0683(3) 0.0587(15) Uani 1 1 d . . . H47A H 0.0114 0.1142 0.1137 0.070 Uiso 1 1 calc R . . O3 O 0.1123(3) 0.0709(3) 0.7869(4) 0.1143(18) Uani 1 1 d . . . O4 O -0.0398(3) 0.0798(3) 0.7380(4) 0.130(2) Uani 1 1 d . . . C48 C -0.0085(5) 0.0384(4) 0.8715(5) 0.110(3) Uani 1 1 d . . . H48A H 0.0444 0.0266 0.9108 0.166 Uiso 1 1 calc R . . H48B H -0.0480 0.0005 0.8591 0.166 Uiso 1 1 calc R . . H48C H -0.0460 0.0720 0.8957 0.166 Uiso 1 1 calc R . . C49 C 0.0271(5) 0.0622(3) 0.7958(5) 0.0787(19) Uani 1 1 d . . . C50 C -0.0257(5) 0.0946(6) 0.6539(5) 0.153(5) Uani 1 1 d . . . H50A H -0.0568 0.0619 0.6168 0.183 Uiso 1 1 calc R . . H50B H 0.0424 0.0946 0.6455 0.183 Uiso 1 1 calc R . . C51 C -0.0681(5) 0.1619(4) 0.6337(5) 0.130(3) Uani 1 1 d . . . H51A H -0.0580 0.1732 0.5763 0.195 Uiso 1 1 calc R . . H51B H -0.0374 0.1939 0.6711 0.195 Uiso 1 1 calc R . . H51C H -0.1357 0.1613 0.6408 0.195 Uiso 1 1 calc R . . 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 0.0400(19) 0.040(2) 0.036(2) 0.0041(17) -0.0012(16) -0.0018(16) N2 0.0413(19) 0.035(2) 0.032(2) -0.0026(16) -0.0017(16) 0.0016(15) N3 0.0380(19) 0.042(2) 0.037(3) 0.0009(18) -0.0056(16) 0.0001(16) N4 0.0450(19) 0.039(2) 0.032(2) 0.0016(17) -0.0038(16) 0.0017(16) C1 0.049(2) 0.031(2) 0.034(3) 0.000(2) 0.005(2) -0.0048(19) C2 0.046(3) 0.051(3) 0.053(4) 0.006(3) -0.003(2) -0.004(2) C3 0.049(3) 0.054(3) 0.052(4) 0.009(3) 0.004(2) -0.012(2) C4 0.068(3) 0.039(3) 0.035(3) 0.003(2) 0.010(2) -0.003(2) C5 0.048(2) 0.032(2) 0.029(3) 0.0029(19) 0.0014(19) -0.0045(19) C6 0.043(2) 0.031(2) 0.028(3) -0.0032(19) 0.0037(18) -0.0013(18) C7 0.041(2) 0.028(2) 0.026(3) -0.0034(18) 0.0013(18) 0.0015(17) C8 0.046(2) 0.033(2) 0.029(3) -0.0026(19) 0.0048(19) 0.0030(19) C9 0.047(3) 0.030(2) 0.045(3) -0.004(2) -0.002(2) 0.0007(19) C10 0.049(3) 0.046(3) 0.047(3) 0.010(2) -0.009(2) -0.001(2) C11 0.056(3) 0.052(3) 0.055(4) 0.007(3) -0.011(2) -0.005(2) C12 0.047(3) 0.070(4) 0.069(4) 0.020(3) -0.014(3) -0.012(3) C13 0.037(2) 0.066(3) 0.060(4) 0.013(3) -0.005(2) -0.006(2) C14 0.045(2) 0.038(3) 0.044(3) -0.001(2) -0.001(2) 0.001(2) C15 0.044(2) 0.031(2) 0.029(3) 0.0022(19) 0.0017(19) -0.0041(19) C16 0.038(2) 0.025(2) 0.037(3) -0.0006(18) 0.0078(18) -0.0001(17) C17 0.045(2) 0.029(2) 0.033(3) 0.0014(19) 0.0056(19) 0.0043(19) C18 0.049(2) 0.038(3) 0.045(3) 0.003(2) 0.003(2) -0.006(2) C19 0.050(3) 0.043(3) 0.042(3) 0.007(2) 0.006(2) -0.001(2) C20 0.065(3) 0.035(3) 0.036(3) 0.005(2) 0.008(2) 0.000(2) C21 0.047(2) 0.041(3) 0.034(3) 0.000(2) 0.003(2) 0.010(2) C22 0.048(2) 0.031(2) 0.029(3) -0.0066(19) 0.0073(19) -0.0008(19) C23 0.041(2) 0.032(2) 0.024(3) -0.0014(19) 0.0038(17) 0.0022(18) C24 0.037(2) 0.031(2) 0.035(3) -0.0048(19) 0.0056(18) 0.0007(18) N5 0.041(2) 0.082(4) 0.083(4) -0.049(3) 0.002(2) 0.003(2) C25 0.055(3) 0.084(4) 0.094(5) -0.058(4) 0.023(3) -0.018(3) C26 0.051(3) 0.058(3) 0.061(4) -0.012(3) 0.020(2) -0.009(2) C27 0.076(4) 0.071(4) 0.069(5) -0.013(3) 0.027(3) -0.029(3) C28 0.098(4) 0.054(4) 0.065(5) 0.009(3) -0.004(3) 0.003(3) C29 0.045(3) 0.055(3) 0.067(4) -0.025(3) 0.011(2) 0.002(2) C30 0.066(3) 0.057(4) 0.074(5) -0.015(3) 0.024(3) -0.011(3) C31 0.090(4) 0.039(3) 0.075(5) -0.005(3) 0.036(3) -0.004(3) C32 0.075(3) 0.061(4) 0.071(5) 0.000(3) 0.018(3) 0.014(3) C33 0.050(6) 0.035(6) 0.046(7) 0.001(5) 0.008(5) 0.001(5) C34 0.055(5) 0.057(6) 0.053(6) -0.015(5) 0.009(5) -0.008(5) C35 0.082(5) 0.030(4) 0.018(4) -0.005(3) 0.007(4) 0.003(4) C36 0.102(6) 0.071(5) 0.081(6) 0.010(5) 0.023(5) -0.009(5) C33' 0.048(6) 0.052(7) 0.047(7) -0.001(5) 0.011(5) -0.001(5) C34' 0.080(6) 0.036(5) 0.049(6) -0.007(5) 0.010(5) 0.021(5) C35' 0.107(6) 0.055(5) 0.072(6) 0.010(5) 0.014(5) 0.032(5) C36' 0.115(6) 0.074(5) 0.097(6) 0.002(5) 0.013(5) 0.015(5) C37 0.052(5) 0.049(6) 0.056(7) -0.015(5) 0.003(5) -0.008(5) C38 0.048(5) 0.064(6) 0.058(7) -0.024(5) 0.009(4) -0.002(5) C39 0.049(4) 0.062(5) 0.056(6) -0.014(5) 0.003(4) -0.009(4) C40 0.049(5) 0.069(5) 0.053(5) -0.008(4) -0.003(4) -0.003(4) C37' 0.029(4) 0.043(5) 0.032(6) -0.005(4) 0.003(4) -0.006(4) C38' 0.036(4) 0.043(5) 0.047(6) -0.002(4) 0.002(4) 0.003(4) C39' 0.044(5) 0.065(5) 0.048(5) 0.002(4) 0.003(4) -0.002(4) C40' 0.048(4) 0.065(5) 0.055(5) -0.002(4) -0.006(4) 0.002(4) O1 0.056(2) 0.075(3) 0.064(3) 0.020(2) -0.0152(18) -0.0005(18) O2 0.0388(16) 0.065(2) 0.057(3) 0.0095(19) -0.0026(15) -0.0019(16) C41 0.049(3) 0.059(3) 0.048(4) 0.001(3) -0.004(2) -0.004(2) C42 0.044(2) 0.050(3) 0.033(3) -0.003(2) -0.005(2) -0.001(2) C43 0.044(2) 0.053(3) 0.052(4) 0.005(3) 0.002(2) -0.006(2) C44 0.047(3) 0.063(4) 0.062(4) 0.001(3) -0.010(2) -0.008(2) C45 0.039(2) 0.087(4) 0.055(4) 0.003(3) -0.012(2) 0.000(3) C46 0.049(3) 0.091(4) 0.060(4) 0.006(3) -0.002(3) -0.015(3) C47 0.048(3) 0.076(4) 0.051(4) 0.013(3) -0.005(2) -0.012(3) O3 0.069(3) 0.146(5) 0.126(5) -0.007(4) -0.002(3) -0.005(3) O4 0.064(3) 0.223(7) 0.104(5) 0.046(5) 0.001(3) 0.023(3) C48 0.125(6) 0.088(6) 0.120(8) -0.002(5) 0.022(5) -0.019(4) C49 0.087(5) 0.069(4) 0.081(6) -0.005(4) 0.018(4) -0.014(4) C50 0.111(6) 0.277(13) 0.072(6) 0.095(7) 0.016(5) 0.076(7) C51 0.111(5) 0.150(8) 0.121(8) 0.037(6) -0.043(5) -0.057(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C24 1.358(5) . ? N1 C1 1.385(5) . ? N1 H1 0.8600 . ? N2 C8 1.324(5) . ? N2 C9 1.367(5) . ? N3 C15 1.319(5) . ? N3 C14 1.353(5) . ? N4 C23 1.380(5) . ? N4 C22 1.381(5) . ? N4 H4 0.8600 . ? C1 C2 1.397(6) . ? C1 C6 1.424(5) . ? C2 C3 1.370(6) . ? C2 H2A 0.9300 . ? C3 C4 1.410(6) . ? C3 H3A 0.9300 . ? C4 C5 1.376(6) . ? C4 H4A 0.9300 . ? C5 C6 1.386(6) . ? C5 H5A 0.9300 . ? C6 C7 1.443(5) . ? C7 C24 1.387(6) . ? C7 C8 1.451(5) . ? C8 C15 1.456(6) . ? C9 C14 1.418(6) . ? C9 C10 1.415(6) . ? C10 C11 1.359(6) . ? C10 H10A 0.9300 . ? C11 C12 1.418(7) . ? C11 H11A 0.9300 . ? C12 C13 1.371(6) . ? C12 H12A 0.9300 . ? C13 C14 1.427(6) . ? C13 H13A 0.9300 . ? C15 C16 1.459(6) . ? C16 C23 1.385(5) . ? C16 C17 1.435(6) . ? C17 C18 1.408(6) . ? C17 C22 1.412(5) . ? C18 C19 1.376(6) . ? C18 H18A 0.9300 . ? C19 C20 1.390(6) . ? C19 H19A 0.9300 . ? C20 C21 1.390(6) . ? C20 H20A 0.9300 . ? C21 C22 1.396(6) . ? C21 H21A 0.9300 . ? C23 C24 1.415(6) . ? N5 C33' 1.266(11) . ? N5 C29 1.511(6) . ? N5 C25 1.516(7) . ? N5 C37 1.539(9) . ? N5 C37' 1.612(9) . ? N5 C33 1.791(10) . ? C25 C26 1.517(6) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.539(8) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.493(7) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.522(7) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.524(6) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.514(7) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.553(8) . ? C33 H33A 0.9700 . ? C33 H33D 0.9700 . ? C34 C35 1.528(8) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.554(8) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C33' C34' 1.560(9) . ? C33' H33B 0.9700 . ? C33' H33C 0.9700 . ? C34' C35' 1.532(8) . ? C34' H34C 0.9700 . ? C34' H34D 0.9700 . ? C35' C36' 1.437(9) . ? C35' H35C 0.9700 . ? C35' H35D 0.9700 . ? C36' H36D 0.9600 . ? C36' H36E 0.9600 . ? C36' H36F 0.9600 . ? C37 C38 1.520(8) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.543(8) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.541(9) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C37' C38' 1.527(8) . ? C37' H37C 0.9700 . ? C37' H37D 0.9700 . ? C38' C39' 1.556(9) . ? C38' H38C 0.9700 . ? C38' H38D 0.9700 . ? C39' C40' 1.520(8) . ? C39' H39C 0.9700 . ? C39' H39D 0.9700 . ? C40' H40D 0.9600 . ? C40' H40E 0.9600 . ? C40' H40F 0.9600 . ? O1 C41 1.278(6) . ? O2 C41 1.257(6) . ? C41 C42 1.505(6) . ? C42 C43 1.367(6) . ? C42 C47 1.391(6) . ? C43 C44 1.383(6) . ? C43 H43A 0.9300 . ? C44 C45 1.350(7) . ? C44 H44A 0.9300 . ? C45 C46 1.378(7) . ? C45 H45A 0.9300 . ? C46 C47 1.389(6) . ? C46 H46A 0.9300 . ? C47 H47A 0.9300 . ? O3 C49 1.221(7) . ? O4 C49 1.309(8) . ? O4 C50 1.398(8) . ? C48 C49 1.421(9) . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C50 C51 1.518(11) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 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 C24 N1 C1 108.3(3) . . ? C24 N1 H1 125.8 . . ? C1 N1 H1 125.8 . . ? C8 N2 C9 117.3(4) . . ? C15 N3 C14 118.1(4) . . ? C23 N4 C22 107.7(3) . . ? C23 N4 H4 126.1 . . ? C22 N4 H4 126.1 . . ? N1 C1 C2 129.4(4) . . ? N1 C1 C6 109.0(3) . . ? C2 C1 C6 121.7(4) . . ? C3 C2 C1 117.0(4) . . ? C3 C2 H2A 121.5 . . ? C1 C2 H2A 121.5 . . ? C2 C3 C4 122.3(4) . . ? C2 C3 H3A 118.9 . . ? C4 C3 H3A 118.9 . . ? C5 C4 C3 120.5(4) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 119.1(4) . . ? C4 C5 H5A 120.5 . . ? C6 C5 H5A 120.5 . . ? C5 C6 C1 119.5(4) . . ? C5 C6 C7 135.3(4) . . ? C1 C6 C7 105.2(3) . . ? C24 C7 C6 107.1(3) . . ? C24 C7 C8 120.8(4) . . ? C6 C7 C8 132.0(4) . . ? N2 C8 C7 120.2(4) . . ? N2 C8 C15 121.3(4) . . ? C7 C8 C15 118.5(4) . . ? N2 C9 C14 121.0(4) . . ? N2 C9 C10 119.8(4) . . ? C14 C9 C10 119.2(4) . . ? C11 C10 C9 121.4(5) . . ? C11 C10 H10A 119.3 . . ? C9 C10 H10A 119.3 . . ? C10 C11 C12 119.7(5) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C12 C13 C14 120.4(5) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? N3 C14 C9 121.2(4) . . ? N3 C14 C13 120.3(4) . . ? C9 C14 C13 118.6(4) . . ? N3 C15 C8 120.9(4) . . ? N3 C15 C16 121.1(4) . . ? C8 C15 C16 118.0(3) . . ? C23 C16 C17 107.4(4) . . ? C23 C16 C15 121.0(4) . . ? C17 C16 C15 131.6(4) . . ? C18 C17 C22 118.7(4) . . ? C18 C17 C16 135.6(4) . . ? C22 C17 C16 105.6(3) . . ? C19 C18 C17 118.4(4) . . ? C19 C18 H18A 120.8 . . ? C17 C18 H18A 120.8 . . ? C18 C19 C20 122.3(4) . . ? C18 C19 H19A 118.9 . . ? C20 C19 H19A 118.9 . . ? C21 C20 C19 120.9(4) . . ? C21 C20 H20A 119.5 . . ? C19 C20 H20A 119.5 . . ? C20 C21 C22 117.1(4) . . ? C20 C21 H21A 121.4 . . ? C22 C21 H21A 121.4 . . ? N4 C22 C21 127.9(4) . . ? N4 C22 C17 109.5(4) . . ? C21 C22 C17 122.5(4) . . ? C16 C23 N4 109.7(4) . . ? C16 C23 C24 120.6(4) . . ? N4 C23 C24 129.6(4) . . ? N1 C24 C7 110.4(4) . . ? N1 C24 C23 128.7(4) . . ? C7 C24 C23 120.9(4) . . ? C33' N5 C29 115.5(7) . . ? C33' N5 C25 104.6(6) . . ? C29 N5 C25 112.1(4) . . ? C33' N5 C37 91.3(8) . . ? C29 N5 C37 111.0(5) . . ? C25 N5 C37 120.8(6) . . ? C33' N5 C37' 119.8(7) . . ? C29 N5 C37' 104.7(4) . . ? C25 N5 C37' 99.1(5) . . ? C37 N5 C37' 31.0(5) . . ? C33' N5 C33 13.3(8) . . ? C29 N5 C33 102.2(5) . . ? C25 N5 C33 111.0(5) . . ? C37 N5 C33 97.3(7) . . ? C37' N5 C33 127.8(6) . . ? N5 C25 C26 115.7(4) . . ? N5 C25 H25A 108.3 . . ? C26 C25 H25A 108.3 . . ? N5 C25 H25B 108.3 . . ? C26 C25 H25B 108.3 . . ? H25A C25 H25B 107.4 . . ? C25 C26 C27 111.1(4) . . ? C25 C26 H26A 109.4 . . ? C27 C26 H26A 109.4 . . ? C25 C26 H26B 109.4 . . ? C27 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C28 C27 C26 114.0(4) . . ? C28 C27 H27A 108.7 . . ? C26 C27 H27A 108.7 . . ? C28 C27 H27B 108.7 . . ? C26 C27 H27B 108.7 . . ? H27A C27 H27B 107.6 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N5 C29 C30 115.8(4) . . ? N5 C29 H29A 108.3 . . ? C30 C29 H29A 108.3 . . ? N5 C29 H29B 108.3 . . ? C30 C29 H29B 108.3 . . ? H29A C29 H29B 107.4 . . ? C29 C30 C31 109.7(4) . . ? C29 C30 H30A 109.7 . . ? C31 C30 H30A 109.7 . . ? C29 C30 H30B 109.7 . . ? C31 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? C32 C31 C30 112.3(5) . . ? C32 C31 H31A 109.1 . . ? C30 C31 H31A 109.1 . . ? C32 C31 H31B 109.1 . . ? C30 C31 H31B 109.1 . . ? H31A C31 H31B 107.9 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 N5 124.1(8) . . ? C34 C33 H33A 106.3 . . ? N5 C33 H33A 106.3 . . ? C34 C33 H33D 106.3 . . ? N5 C33 H33D 106.3 . . ? H33A C33 H33D 106.4 . . ? C35 C34 C33 109.8(7) . . ? C35 C34 H34A 109.7 . . ? C33 C34 H34A 109.7 . . ? C35 C34 H34B 109.7 . . ? C33 C34 H34B 109.7 . . ? H34A C34 H34B 108.2 . . ? C34 C35 C36 110.8(7) . . ? C34 C35 H35A 109.5 . . ? C36 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? C36 C35 H35B 109.5 . . ? H35A C35 H35B 108.1 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N5 C33' C34' 112.8(9) . . ? N5 C33' H33B 109.0 . . ? C34' C33' H33B 109.0 . . ? N5 C33' H33C 109.0 . . ? C34' C33' H33C 109.0 . . ? H33B C33' H33C 107.8 . . ? C35' C34' C33' 107.0(7) . . ? C35' C34' H34C 110.3 . . ? C33' C34' H34C 110.3 . . ? C35' C34' H34D 110.3 . . ? C33' C34' H34D 110.3 . . ? H34C C34' H34D 108.6 . . ? C36' C35' C34' 117.2(8) . . ? C36' C35' H35C 108.0 . . ? C34' C35' H35C 108.0 . . ? C36' C35' H35D 108.0 . . ? C34' C35' H35D 108.0 . . ? H35C C35' H35D 107.2 . . ? C35' C36' H36D 109.5 . . ? C35' C36' H36E 109.5 . . ? H36D C36' H36E 109.5 . . ? C35' C36' H36F 109.4 . . ? H36D C36' H36F 109.5 . . ? H36E C36' H36F 109.5 . . ? C38 C37 N5 118.1(7) . . ? C38 C37 H37A 107.8 . . ? N5 C37 H37A 107.8 . . ? C38 C37 H37B 107.8 . . ? N5 C37 H37B 107.8 . . ? H37A C37 H37B 107.1 . . ? C37 C38 C39 109.9(6) . . ? C37 C38 H38A 109.7 . . ? C39 C38 H38A 109.7 . . ? C37 C38 H38B 109.7 . . ? C39 C38 H38B 109.7 . . ? H38A C38 H38B 108.2 . . ? C40 C39 C38 108.5(7) . . ? C40 C39 H39A 110.0 . . ? C38 C39 H39A 110.0 . . ? C40 C39 H39B 110.0 . . ? C38 C39 H39B 110.0 . . ? H39A C39 H39B 108.4 . . ? 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 . . ? C38' C37' N5 115.3(6) . . ? C38' C37' H37C 108.5 . . ? N5 C37' H37C 108.5 . . ? C38' C37' H37D 108.5 . . ? N5 C37' H37D 108.5 . . ? H37C C37' H37D 107.5 . . ? C37' C38' C39' 106.9(6) . . ? C37' C38' H38C 110.3 . . ? C39' C38' H38C 110.3 . . ? C37' C38' H38D 110.3 . . ? C39' C38' H38D 110.3 . . ? H38C C38' H38D 108.6 . . ? C40' C39' C38' 109.6(7) . . ? C40' C39' H39C 109.8 . . ? C38' C39' H39C 109.8 . . ? C40' C39' H39D 109.8 . . ? C38' C39' H39D 109.8 . . ? H39C C39' H39D 108.2 . . ? C39' C40' H40D 109.5 . . ? C39' C40' H40E 109.5 . . ? H40D C40' H40E 109.5 . . ? C39' C40' H40F 109.5 . . ? H40D C40' H40F 109.5 . . ? H40E C40' H40F 109.5 . . ? O2 C41 O1 125.3(4) . . ? O2 C41 C42 118.6(4) . . ? O1 C41 C42 116.1(4) . . ? C43 C42 C47 118.7(4) . . ? C43 C42 C41 120.9(4) . . ? C47 C42 C41 120.3(4) . . ? C42 C43 C44 121.0(5) . . ? C42 C43 H43A 119.5 . . ? C44 C43 H43A 119.5 . . ? C45 C44 C43 121.3(5) . . ? C45 C44 H44A 119.4 . . ? C43 C44 H44A 119.4 . . ? C44 C45 C46 118.2(4) . . ? C44 C45 H45A 120.9 . . ? C46 C45 H45A 120.9 . . ? C45 C46 C47 121.9(5) . . ? C45 C46 H46A 119.1 . . ? C47 C46 H46A 119.1 . . ? C46 C47 C42 118.8(5) . . ? C46 C47 H47A 120.6 . . ? C42 C47 H47A 120.6 . . ? C49 O4 C50 125.7(6) . . ? C49 C48 H48A 109.5 . . ? C49 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C49 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? O3 C49 O4 121.8(7) . . ? O3 C49 C48 123.7(7) . . ? O4 C49 C48 114.2(6) . . ? O4 C50 C51 108.4(8) . . ? O4 C50 H50A 110.0 . . ? C51 C50 H50A 110.0 . . ? O4 C50 H50B 110.0 . . ? C51 C50 H50B 110.0 . . ? H50A C50 H50B 108.4 . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 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 C24 N1 C1 C2 178.9(4) . . . . ? C24 N1 C1 C6 -0.5(5) . . . . ? N1 C1 C2 C3 -179.5(5) . . . . ? C6 C1 C2 C3 -0.1(7) . . . . ? C1 C2 C3 C4 0.0(8) . . . . ? C2 C3 C4 C5 0.4(7) . . . . ? C3 C4 C5 C6 -0.6(7) . . . . ? C4 C5 C6 C1 0.5(6) . . . . ? C4 C5 C6 C7 -179.5(4) . . . . ? N1 C1 C6 C5 179.3(4) . . . . ? C2 C1 C6 C5 -0.2(6) . . . . ? N1 C1 C6 C7 -0.7(4) . . . . ? C2 C1 C6 C7 179.8(4) . . . . ? C5 C6 C7 C24 -178.4(5) . . . . ? C1 C6 C7 C24 1.6(4) . . . . ? C5 C6 C7 C8 2.0(8) . . . . ? C1 C6 C7 C8 -178.0(4) . . . . ? C9 N2 C8 C7 178.4(4) . . . . ? C9 N2 C8 C15 -2.3(6) . . . . ? C24 C7 C8 N2 -179.9(4) . . . . ? C6 C7 C8 N2 -0.3(7) . . . . ? C24 C7 C8 C15 0.9(6) . . . . ? C6 C7 C8 C15 -179.6(4) . . . . ? C8 N2 C9 C14 -1.4(6) . . . . ? C8 N2 C9 C10 178.6(4) . . . . ? N2 C9 C10 C11 177.0(4) . . . . ? C14 C9 C10 C11 -3.0(7) . . . . ? C9 C10 C11 C12 0.5(8) . . . . ? C10 C11 C12 C13 0.9(8) . . . . ? C11 C12 C13 C14 0.2(8) . . . . ? C15 N3 C14 C9 -1.1(6) . . . . ? C15 N3 C14 C13 178.1(4) . . . . ? N2 C9 C14 N3 3.2(7) . . . . ? C10 C9 C14 N3 -176.7(4) . . . . ? N2 C9 C14 C13 -176.0(4) . . . . ? C10 C9 C14 C13 4.0(7) . . . . ? C12 C13 C14 N3 178.1(5) . . . . ? C12 C13 C14 C9 -2.7(7) . . . . ? C14 N3 C15 C8 -2.6(6) . . . . ? C14 N3 C15 C16 178.6(4) . . . . ? N2 C8 C15 N3 4.5(6) . . . . ? C7 C8 C15 N3 -176.2(4) . . . . ? N2 C8 C15 C16 -176.6(4) . . . . ? C7 C8 C15 C16 2.7(6) . . . . ? N3 C15 C16 C23 175.3(4) . . . . ? C8 C15 C16 C23 -3.6(6) . . . . ? N3 C15 C16 C17 -6.9(7) . . . . ? C8 C15 C16 C17 174.2(4) . . . . ? C23 C16 C17 C18 179.4(5) . . . . ? C15 C16 C17 C18 1.3(8) . . . . ? C23 C16 C17 C22 -0.4(5) . . . . ? C15 C16 C17 C22 -178.5(4) . . . . ? C22 C17 C18 C19 1.1(6) . . . . ? C16 C17 C18 C19 -178.6(5) . . . . ? C17 C18 C19 C20 0.3(7) . . . . ? C18 C19 C20 C21 -0.6(7) . . . . ? C19 C20 C21 C22 -0.5(7) . . . . ? C23 N4 C22 C21 -176.9(4) . . . . ? C23 N4 C22 C17 0.5(5) . . . . ? C20 C21 C22 N4 179.0(4) . . . . ? C20 C21 C22 C17 1.9(6) . . . . ? C18 C17 C22 N4 -179.9(4) . . . . ? C16 C17 C22 N4 0.0(5) . . . . ? C18 C17 C22 C21 -2.3(6) . . . . ? C16 C17 C22 C21 177.5(4) . . . . ? C17 C16 C23 N4 0.7(5) . . . . ? C15 C16 C23 N4 179.0(4) . . . . ? C17 C16 C23 C24 -177.4(4) . . . . ? C15 C16 C23 C24 0.9(6) . . . . ? C22 N4 C23 C16 -0.7(5) . . . . ? C22 N4 C23 C24 177.1(4) . . . . ? C1 N1 C24 C7 1.6(5) . . . . ? C1 N1 C24 C23 -177.0(4) . . . . ? C6 C7 C24 N1 -2.0(5) . . . . ? C8 C7 C24 N1 177.6(4) . . . . ? C6 C7 C24 C23 176.7(4) . . . . ? C8 C7 C24 C23 -3.7(6) . . . . ? C16 C23 C24 N1 -178.8(4) . . . . ? N4 C23 C24 N1 3.6(7) . . . . ? C16 C23 C24 C7 2.8(6) . . . . ? N4 C23 C24 C7 -174.9(4) . . . . ? C33' N5 C25 C26 79.4(8) . . . . ? C29 N5 C25 C26 -46.4(7) . . . . ? C37 N5 C25 C26 179.8(6) . . . . ? C37' N5 C25 C26 -156.5(5) . . . . ? C33 N5 C25 C26 67.1(7) . . . . ? N5 C25 C26 C27 -178.9(5) . . . . ? C25 C26 C27 C28 -173.0(5) . . . . ? C33' N5 C29 C30 -176.0(7) . . . . ? C25 N5 C29 C30 -56.4(6) . . . . ? C37 N5 C29 C30 82.0(8) . . . . ? C37' N5 C29 C30 50.0(7) . . . . ? C33 N5 C29 C30 -175.2(5) . . . . ? N5 C29 C30 C31 172.5(4) . . . . ? C29 C30 C31 C32 -70.4(6) . . . . ? C33' N5 C33 C34 122(4) . . . . ? C29 N5 C33 C34 -55.4(11) . . . . ? C25 N5 C33 C34 -175.0(8) . . . . ? C37 N5 C33 C34 58.0(11) . . . . ? C37' N5 C33 C34 64.3(12) . . . . ? N5 C33 C34 C35 174.2(8) . . . . ? C33 C34 C35 C36 179.1(9) . . . . ? C29 N5 C33' C34' -62.1(11) . . . . ? C25 N5 C33' C34' 174.2(8) . . . . ? C37 N5 C33' C34' 51.9(10) . . . . ? C37' N5 C33' C34' 64.5(12) . . . . ? C33 N5 C33' C34' -65(3) . . . . ? N5 C33' C34' C35' 176.8(9) . . . . ? C33' C34' C35' C36' -147.9(12) . . . . ? C33' N5 C37 C38 54.4(11) . . . . ? C29 N5 C37 C38 172.4(9) . . . . ? C25 N5 C37 C38 -53.4(12) . . . . ? C37' N5 C37 C38 -103.9(15) . . . . ? C33 N5 C37 C38 66.4(11) . . . . ? N5 C37 C38 C39 164.3(8) . . . . ? C37 C38 C39 C40 -73.2(12) . . . . ? C33' N5 C37' C38' 46.4(12) . . . . ? C29 N5 C37' C38' 177.9(7) . . . . ? C25 N5 C37' C38' -66.3(9) . . . . ? C37 N5 C37' C38' 71.5(11) . . . . ? C33 N5 C37' C38' 59.3(11) . . . . ? N5 C37' C38' C39' -165.3(8) . . . . ? C37' C38' C39' C40' -175.0(10) . . . . ? O2 C41 C42 C43 8.3(7) . . . . ? O1 C41 C42 C43 -172.3(5) . . . . ? O2 C41 C42 C47 -169.3(5) . . . . ? O1 C41 C42 C47 10.1(7) . . . . ? C47 C42 C43 C44 -2.3(8) . . . . ? C41 C42 C43 C44 -180.0(5) . . . . ? C42 C43 C44 C45 1.5(8) . . . . ? C43 C44 C45 C46 1.2(8) . . . . ? C44 C45 C46 C47 -3.1(9) . . . . ? C45 C46 C47 C42 2.3(9) . . . . ? C43 C42 C47 C46 0.5(8) . . . . ? C41 C42 C47 C46 178.1(5) . . . . ? C50 O4 C49 O3 16.8(13) . . . . ? C50 O4 C49 C48 -169.0(9) . . . . ? C49 O4 C50 C51 -126.5(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.455 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.061 # ---------------Attachment 'DIPZ-F.CIF' data_r81233a1 _database_code_depnum_ccdc_archive 'CCDC 748208' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DIPZ+F _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H50 F N5' _chemical_formula_weight 619.85 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' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 22.428(6) _cell_length_b 8.4214(17) _cell_length_c 19.787(8) _cell_angle_alpha 90.00 _cell_angle_beta 113.21(3) _cell_angle_gamma 90.00 _cell_volume 3434.8(18) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3192 _cell_measurement_theta_min 2.240 _cell_measurement_theta_max 25.997 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9809 _exptl_absorpt_correction_T_max 0.9926 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11141 _diffrn_reflns_av_R_equivalents 0.1329 _diffrn_reflns_av_sigmaI/netI 0.1371 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3031 _reflns_number_gt 2112 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The restraints are made to refine the bond length of N-H in the two indole groups in DIPZ. The length is fixed at 0.90 as the theoretical bond length of N-H. ; _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^)+(0.0600P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3031 _refine_ls_number_parameters 427 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0972 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1297 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.010 _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 N1 N -0.02020(19) 0.9715(5) 0.1437(2) 0.0353(11) Uani 1 1 d D . . N2 N 0.12783(18) 0.7457(5) 0.3603(2) 0.0323(11) Uani 1 1 d . . . N3 N 0.04217(17) 0.8007(5) 0.4335(2) 0.0312(10) Uani 1 1 d . . . N4 N -0.11281(19) 1.0334(6) 0.2229(2) 0.0363(12) Uani 1 1 d D . . C1 C 0.0350(2) 0.9248(6) 0.1318(3) 0.0327(13) Uani 1 1 d . . . C2 C 0.0471(3) 0.9341(7) 0.0688(3) 0.0414(15) Uani 1 1 d . . . H2 H 0.0166 0.9764 0.0255 0.050 Uiso 1 1 calc R . . C3 C 0.1060(3) 0.8785(7) 0.0721(3) 0.0439(15) Uani 1 1 d . . . H3 H 0.1150 0.8819 0.0300 0.053 Uiso 1 1 calc R . . C4 C 0.1526(3) 0.8172(7) 0.1371(3) 0.0401(14) Uani 1 1 d . . . H4 H 0.1923 0.7829 0.1380 0.048 Uiso 1 1 calc R . . C5 C 0.1402(2) 0.8068(7) 0.2002(3) 0.0400(15) Uani 1 1 d . . . H5 H 0.1710 0.7640 0.2431 0.048 Uiso 1 1 calc R . . C6 C 0.0807(3) 0.8617(6) 0.1985(3) 0.0358(14) Uani 1 1 d . . . C7 C 0.0514(2) 0.8687(6) 0.2517(3) 0.0299(12) Uani 1 1 d . . . C8 C 0.0702(2) 0.8180(6) 0.3268(3) 0.0304(13) Uani 1 1 d . . . C9 C 0.1428(2) 0.6982(6) 0.4308(3) 0.0315(13) Uani 1 1 d . . . C10 C 0.2021(2) 0.6161(7) 0.4687(3) 0.0391(15) Uani 1 1 d . . . H10 H 0.2293 0.5934 0.4447 0.047 Uiso 1 1 calc R . . C11 C 0.2194(3) 0.5701(7) 0.5402(3) 0.0430(15) Uani 1 1 d . . . H11 H 0.2585 0.5175 0.5646 0.052 Uiso 1 1 calc R . . C12 C 0.1783(2) 0.6023(8) 0.5769(3) 0.0454(16) Uani 1 1 d . . . H12 H 0.1905 0.5700 0.6255 0.054 Uiso 1 1 calc R . . C13 C 0.1206(2) 0.6804(7) 0.5424(3) 0.0418(15) Uani 1 1 d . . . H13 H 0.0945 0.7026 0.5679 0.050 Uiso 1 1 calc R . . C14 C 0.1004(2) 0.7277(6) 0.4673(3) 0.0351(13) Uani 1 1 d . . . C15 C 0.0266(2) 0.8433(6) 0.3640(3) 0.0311(13) Uani 1 1 d . . . C16 C -0.0355(2) 0.9161(6) 0.3234(3) 0.0321(13) Uani 1 1 d . . . C17 C -0.0907(2) 0.9518(6) 0.3408(3) 0.0345(13) Uani 1 1 d . . . C18 C -0.1059(2) 0.9313(6) 0.4021(3) 0.0331(13) Uani 1 1 d . . . H18 H -0.0760 0.8842 0.4444 0.040 Uiso 1 1 calc R . . C19 C -0.1659(2) 0.9812(7) 0.4002(3) 0.0403(14) Uani 1 1 d . . . H19 H -0.1762 0.9660 0.4409 0.048 Uiso 1 1 calc R . . C20 C -0.2099(2) 1.0532(7) 0.3377(3) 0.0418(15) Uani 1 1 d . . . H20 H -0.2495 1.0872 0.3373 0.050 Uiso 1 1 calc R . . C21 C -0.1965(2) 1.0765(6) 0.2749(3) 0.0430(16) Uani 1 1 d . . . H21 H -0.2265 1.1246 0.2330 0.052 Uiso 1 1 calc R . . C22 C -0.1369(2) 1.0251(6) 0.2778(3) 0.0334(13) Uani 1 1 d . . . C23 C -0.0524(2) 0.9647(6) 0.2510(3) 0.0339(14) Uani 1 1 d . . . C24 C -0.0099(2) 0.9394(6) 0.2154(3) 0.0306(13) Uani 1 1 d . . . N5 N 0.39372(19) 0.0183(4) 0.0378(2) 0.0313(10) Uani 1 1 d . . . C25 C 0.4451(2) -0.0992(6) 0.0843(3) 0.0358(14) Uani 1 1 d . . . H25A H 0.4255 -0.1689 0.1087 0.043 Uiso 1 1 calc R . . H25B H 0.4574 -0.1643 0.0514 0.043 Uiso 1 1 calc R . . C26 C 0.5067(2) -0.0298(6) 0.1423(3) 0.0376(14) Uani 1 1 d . . . H26A H 0.5303 0.0290 0.1187 0.045 Uiso 1 1 calc R . . H26B H 0.4954 0.0428 0.1735 0.045 Uiso 1 1 calc R . . C27 C 0.5491(2) -0.1628(7) 0.1888(3) 0.0371(14) Uani 1 1 d . . . H27A H 0.5266 -0.2142 0.2158 0.045 Uiso 1 1 calc R . . H27B H 0.5556 -0.2414 0.1565 0.045 Uiso 1 1 calc R . . C28 C 0.6149(2) -0.1055(7) 0.2429(3) 0.0454(15) Uani 1 1 d . . . H28A H 0.6379 -0.0569 0.2164 0.068 Uiso 1 1 calc R . . H28B H 0.6393 -0.1941 0.2706 0.068 Uiso 1 1 calc R . . H28C H 0.6089 -0.0293 0.2757 0.068 Uiso 1 1 calc R . . C29 C 0.3717(2) 0.1242(6) 0.0863(3) 0.0367(13) Uani 1 1 d . . . H29A H 0.4093 0.1798 0.1207 0.044 Uiso 1 1 calc R . . H29B H 0.3421 0.2036 0.0553 0.044 Uiso 1 1 calc R . . C30 C 0.3384(3) 0.0393(7) 0.1297(3) 0.0439(15) Uani 1 1 d . . . H30A H 0.2951 0.0073 0.0969 0.053 Uiso 1 1 calc R . . H30B H 0.3626 -0.0554 0.1524 0.053 Uiso 1 1 calc R . . C31 C 0.3344(3) 0.1494(7) 0.1886(3) 0.0448(15) Uani 1 1 d . . . H31A H 0.3128 0.2466 0.1654 0.054 Uiso 1 1 calc R . . H31B H 0.3781 0.1770 0.2221 0.054 Uiso 1 1 calc R . . C32 C 0.2985(3) 0.0789(9) 0.2328(3) 0.065(2) Uani 1 1 d . . . H32A H 0.2536 0.0655 0.2015 0.097 Uiso 1 1 calc R . . H32B H 0.3024 0.1490 0.2726 0.097 Uiso 1 1 calc R . . H32C H 0.3171 -0.0224 0.2523 0.097 Uiso 1 1 calc R . . C33 C 0.3373(2) -0.0794(6) -0.0137(3) 0.0331(12) Uani 1 1 d . . . H33A H 0.3201 -0.1421 0.0156 0.040 Uiso 1 1 calc R . . H33B H 0.3536 -0.1527 -0.0403 0.040 Uiso 1 1 calc R . . C34 C 0.2820(2) 0.0167(7) -0.0694(3) 0.0409(14) Uani 1 1 d . . . H34A H 0.2971 0.0699 -0.1032 0.049 Uiso 1 1 calc R . . H34B H 0.2676 0.0970 -0.0440 0.049 Uiso 1 1 calc R . . C35 C 0.2249(2) -0.0947(7) -0.1125(3) 0.0399(15) Uani 1 1 d . . . H35A H 0.1956 -0.0399 -0.1561 0.048 Uiso 1 1 calc R . . H35B H 0.2416 -0.1871 -0.1286 0.048 Uiso 1 1 calc R . . C36 C 0.1874(3) -0.1489(8) -0.0681(3) 0.0521(17) Uani 1 1 d . . . H36A H 0.2147 -0.2142 -0.0281 0.078 Uiso 1 1 calc R . . H36B H 0.1503 -0.2089 -0.0989 0.078 Uiso 1 1 calc R . . H36C H 0.1734 -0.0579 -0.0489 0.078 Uiso 1 1 calc R . . C37 C 0.4212(2) 0.1265(6) -0.0040(3) 0.0348(13) Uani 1 1 d . . . H37A H 0.4564 0.1875 0.0314 0.042 Uiso 1 1 calc R . . H37B H 0.3877 0.2010 -0.0323 0.042 Uiso 1 1 calc R . . C38 C 0.4466(3) 0.0441(7) -0.0561(3) 0.0429(15) Uani 1 1 d . . . H38A H 0.4836 -0.0217 -0.0278 0.051 Uiso 1 1 calc R . . H38B H 0.4131 -0.0242 -0.0894 0.051 Uiso 1 1 calc R . . C39 C 0.4665(3) 0.1631(8) -0.0996(3) 0.0557(17) Uani 1 1 d . . . H39A H 0.4292 0.2288 -0.1267 0.067 Uiso 1 1 calc R . . H39B H 0.4993 0.2316 -0.0654 0.067 Uiso 1 1 calc R . . C40 C 0.4923(3) 0.0973(8) -0.1526(4) 0.0566(18) Uani 1 1 d . . . H40A H 0.5329 0.0450 -0.1261 0.085 Uiso 1 1 calc R . . H40B H 0.4988 0.1821 -0.1814 0.085 Uiso 1 1 calc R . . H40C H 0.4619 0.0224 -0.1845 0.085 Uiso 1 1 calc R . . F1 F 0.86294(14) 0.0968(4) 0.0854(2) 0.0656(12) Uani 1 1 d . . . H4A H -0.133(4) 1.058(11) 0.1745(15) 0.15(4) Uiso 1 1 d D . . H1A H -0.0581(17) 1.014(7) 0.112(3) 0.07(2) Uiso 1 1 d 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 N1 0.038(2) 0.038(2) 0.032(2) 0.001(2) 0.016(2) -0.010(2) N2 0.032(2) 0.035(2) 0.037(2) -0.003(2) 0.0210(19) 0.0002(19) N3 0.032(2) 0.038(2) 0.028(2) -0.001(2) 0.0159(18) -0.0011(19) N4 0.031(2) 0.033(2) 0.047(3) -0.002(3) 0.017(2) -0.0043(19) C1 0.036(3) 0.033(3) 0.035(3) -0.006(3) 0.019(2) -0.009(2) C2 0.048(3) 0.038(3) 0.038(3) 0.002(3) 0.018(3) 0.001(3) C3 0.054(3) 0.049(3) 0.041(3) 0.001(3) 0.032(3) 0.002(3) C4 0.043(3) 0.045(3) 0.046(3) -0.003(3) 0.033(3) 0.000(3) C5 0.039(3) 0.040(3) 0.045(3) -0.005(3) 0.020(2) -0.001(2) C6 0.044(3) 0.027(3) 0.046(3) -0.002(3) 0.028(3) -0.008(2) C7 0.038(3) 0.029(2) 0.033(3) -0.001(2) 0.025(2) 0.000(2) C8 0.033(2) 0.025(2) 0.039(3) -0.003(3) 0.021(2) -0.004(2) C9 0.036(3) 0.031(3) 0.034(3) -0.003(3) 0.020(2) -0.003(2) C10 0.037(3) 0.048(3) 0.042(3) -0.003(3) 0.027(3) 0.003(3) C11 0.039(3) 0.054(4) 0.043(3) 0.008(3) 0.025(3) 0.010(3) C12 0.042(3) 0.061(4) 0.039(3) 0.009(3) 0.022(3) 0.009(3) C13 0.042(3) 0.054(4) 0.037(3) -0.005(3) 0.024(3) 0.003(3) C14 0.039(3) 0.033(3) 0.040(3) -0.006(3) 0.022(2) -0.002(2) C15 0.030(2) 0.034(3) 0.035(3) -0.008(3) 0.018(2) -0.009(2) C16 0.031(2) 0.030(2) 0.043(3) -0.011(3) 0.022(2) -0.003(2) C17 0.039(3) 0.029(3) 0.040(3) -0.006(3) 0.021(2) -0.007(2) C18 0.031(2) 0.027(3) 0.046(3) -0.007(3) 0.020(2) -0.005(2) C19 0.037(3) 0.042(3) 0.052(3) -0.005(3) 0.029(3) -0.002(2) C20 0.032(3) 0.042(3) 0.056(4) -0.011(3) 0.021(3) 0.003(2) C21 0.036(3) 0.036(3) 0.052(4) -0.003(3) 0.012(3) 0.003(2) C22 0.032(3) 0.032(3) 0.039(3) 0.002(3) 0.017(2) -0.004(2) C23 0.031(2) 0.032(3) 0.041(3) -0.002(3) 0.016(2) -0.010(2) C24 0.034(3) 0.029(3) 0.034(3) -0.007(3) 0.018(2) -0.009(2) N5 0.038(2) 0.026(2) 0.0301(19) -0.003(2) 0.0146(17) -0.004(2) C25 0.040(3) 0.034(3) 0.033(3) 0.002(3) 0.015(2) 0.004(2) C26 0.044(3) 0.028(2) 0.039(3) -0.007(3) 0.015(2) -0.005(2) C27 0.048(3) 0.035(3) 0.029(3) 0.002(3) 0.017(2) -0.003(3) C28 0.042(3) 0.052(3) 0.039(3) 0.004(3) 0.013(3) 0.000(3) C29 0.041(3) 0.036(3) 0.038(3) -0.009(3) 0.021(2) -0.006(2) C30 0.048(3) 0.045(3) 0.050(4) -0.011(3) 0.032(3) -0.014(3) C31 0.053(3) 0.050(3) 0.040(3) -0.010(3) 0.027(3) -0.008(3) C32 0.071(4) 0.080(5) 0.056(4) -0.020(4) 0.040(3) -0.025(4) C33 0.038(2) 0.035(3) 0.032(3) -0.008(3) 0.019(2) -0.005(2) C34 0.040(3) 0.040(3) 0.044(3) -0.001(3) 0.018(2) -0.001(3) C35 0.036(3) 0.045(3) 0.042(3) -0.009(3) 0.019(2) -0.002(2) C36 0.041(3) 0.062(4) 0.056(4) -0.003(4) 0.021(3) -0.008(3) C37 0.038(2) 0.033(3) 0.041(3) -0.004(3) 0.023(2) -0.005(2) C38 0.049(3) 0.036(3) 0.052(3) 0.005(3) 0.028(3) 0.006(3) C39 0.089(4) 0.039(3) 0.054(4) 0.007(4) 0.044(3) -0.001(3) C40 0.070(4) 0.056(4) 0.061(4) 0.004(4) 0.044(4) 0.001(3) F1 0.0465(18) 0.067(2) 0.065(2) 0.026(2) 0.0026(17) -0.0137(17) _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 N1 C24 1.372(7) . ? N1 C1 1.403(7) . ? N1 H1A 0.908(11) . ? N2 C8 1.343(6) . ? N2 C9 1.360(6) . ? N3 C15 1.328(6) . ? N3 C14 1.358(6) . ? N4 C23 1.373(6) . ? N4 C22 1.392(7) . ? N4 H4A 0.907(11) . ? C1 C2 1.381(8) . ? C1 C6 1.418(7) . ? C2 C3 1.378(8) . ? C2 H2 0.9300 . ? C3 C4 1.398(7) . ? C3 H3 0.9300 . ? C4 C5 1.383(8) . ? C4 H4 0.9300 . ? C5 C6 1.400(8) . ? C5 H5 0.9300 . ? C6 C7 1.445(8) . ? C7 C24 1.409(7) . ? C7 C8 1.440(7) . ? C8 C15 1.454(7) . ? C9 C10 1.422(7) . ? C9 C14 1.423(7) . ? C10 C11 1.366(7) . ? C10 H10 0.9300 . ? C11 C12 1.408(8) . ? C11 H11 0.9300 . ? C12 C13 1.370(7) . ? C12 H12 0.9300 . ? C13 C14 1.430(7) . ? C13 H13 0.9300 . ? C15 C16 1.443(6) . ? C16 C23 1.391(7) . ? C16 C17 1.439(7) . ? C17 C18 1.395(8) . ? C17 C22 1.412(7) . ? C18 C19 1.395(7) . ? C18 H18 0.9300 . ? C19 C20 1.382(8) . ? C19 H19 0.9300 . ? C20 C21 1.402(8) . ? C20 H20 0.9300 . ? C21 C22 1.384(7) . ? C21 H21 0.9300 . ? C23 C24 1.407(7) . ? N5 C37 1.515(7) . ? N5 C33 1.516(6) . ? N5 C25 1.523(6) . ? N5 C29 1.528(7) . ? C25 C26 1.522(6) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.521(7) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.520(6) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.521(8) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.519(8) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.523(8) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.527(6) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.545(7) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.507(8) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C38 1.526(8) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.499(8) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.491(9) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 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 C24 N1 C1 108.5(4) . . ? C24 N1 H1A 121(4) . . ? C1 N1 H1A 130(4) . . ? C8 N2 C9 116.1(5) . . ? C15 N3 C14 116.1(5) . . ? C23 N4 C22 106.7(4) . . ? C23 N4 H4A 122(6) . . ? C22 N4 H4A 130(6) . . ? C2 C1 N1 129.5(4) . . ? C2 C1 C6 122.3(5) . . ? N1 C1 C6 108.2(5) . . ? C3 C2 C1 117.7(5) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 121.5(6) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 120.8(5) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.1(5) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 118.6(6) . . ? C5 C6 C7 134.4(5) . . ? C1 C6 C7 107.0(5) . . ? C24 C7 C8 118.8(5) . . ? C24 C7 C6 106.2(5) . . ? C8 C7 C6 135.0(5) . . ? N2 C8 C7 118.5(5) . . ? N2 C8 C15 121.7(5) . . ? C7 C8 C15 119.8(4) . . ? N2 C9 C10 119.1(5) . . ? N2 C9 C14 121.6(4) . . ? C10 C9 C14 119.3(5) . . ? C11 C10 C9 120.7(5) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.2(5) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 121.1(5) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 120.1(6) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? N3 C14 C9 122.4(4) . . ? N3 C14 C13 119.1(5) . . ? C9 C14 C13 118.6(4) . . ? N3 C15 C16 119.6(5) . . ? N3 C15 C8 122.0(4) . . ? C16 C15 C8 118.4(4) . . ? C23 C16 C17 105.8(4) . . ? C23 C16 C15 120.6(5) . . ? C17 C16 C15 133.5(5) . . ? C18 C17 C22 118.4(5) . . ? C18 C17 C16 135.2(5) . . ? C22 C17 C16 106.4(5) . . ? C19 C18 C17 120.3(5) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 119.8(6) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 121.8(5) . . ? C19 C20 H20 119.1 . . ? C21 C20 H20 119.1 . . ? C22 C21 C20 117.4(5) . . ? C22 C21 H21 121.3 . . ? C20 C21 H21 121.3 . . ? C21 C22 N4 128.2(5) . . ? C21 C22 C17 122.3(6) . . ? N4 C22 C17 109.5(5) . . ? N4 C23 C16 111.5(5) . . ? N4 C23 C24 128.0(5) . . ? C16 C23 C24 120.5(5) . . ? N1 C24 C23 128.1(4) . . ? N1 C24 C7 110.0(5) . . ? C23 C24 C7 121.8(5) . . ? C37 N5 C33 111.8(4) . . ? C37 N5 C25 110.3(4) . . ? C33 N5 C25 106.6(3) . . ? C37 N5 C29 107.1(4) . . ? C33 N5 C29 110.4(4) . . ? C25 N5 C29 110.8(4) . . ? C26 C25 N5 116.9(4) . . ? C26 C25 H25A 108.1 . . ? N5 C25 H25A 108.1 . . ? C26 C25 H25B 108.1 . . ? N5 C25 H25B 108.1 . . ? H25A C25 H25B 107.3 . . ? C27 C26 C25 109.8(4) . . ? C27 C26 H26A 109.7 . . ? C25 C26 H26A 109.7 . . ? C27 C26 H26B 109.7 . . ? C25 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? C28 C27 C26 113.2(4) . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 N5 115.6(4) . . ? C30 C29 H29A 108.4 . . ? N5 C29 H29A 108.4 . . ? C30 C29 H29B 108.4 . . ? N5 C29 H29B 108.4 . . ? H29A C29 H29B 107.4 . . ? C31 C30 C29 109.7(5) . . ? C31 C30 H30A 109.7 . . ? C29 C30 H30A 109.7 . . ? C31 C30 H30B 109.7 . . ? C29 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? C30 C31 C32 114.0(5) . . ? C30 C31 H31A 108.8 . . ? C32 C31 H31A 108.8 . . ? C30 C31 H31B 108.8 . . ? C32 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N5 C33 C34 115.0(4) . . ? N5 C33 H33A 108.5 . . ? C34 C33 H33A 108.5 . . ? N5 C33 H33B 108.5 . . ? C34 C33 H33B 108.5 . . ? H33A C33 H33B 107.5 . . ? C33 C34 C35 109.7(4) . . ? C33 C34 H34A 109.7 . . ? C35 C34 H34A 109.7 . . ? C33 C34 H34B 109.7 . . ? C35 C34 H34B 109.7 . . ? H34A C34 H34B 108.2 . . ? C36 C35 C34 113.1(5) . . ? C36 C35 H35A 109.0 . . ? C34 C35 H35A 109.0 . . ? C36 C35 H35B 109.0 . . ? C34 C35 H35B 109.0 . . ? H35A C35 H35B 107.8 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N5 C37 C38 115.8(4) . . ? N5 C37 H37A 108.3 . . ? C38 C37 H37A 108.3 . . ? N5 C37 H37B 108.3 . . ? C38 C37 H37B 108.3 . . ? H37A C37 H37B 107.4 . . ? C39 C38 C37 111.0(5) . . ? C39 C38 H38A 109.4 . . ? C37 C38 H38A 109.4 . . ? C39 C38 H38B 109.4 . . ? C37 C38 H38B 109.4 . . ? H38A C38 H38B 108.0 . . ? C40 C39 C38 116.2(5) . . ? C40 C39 H39A 108.2 . . ? C38 C39 H39A 108.2 . . ? C40 C39 H39B 108.2 . . ? C38 C39 H39B 108.2 . . ? H39A C39 H39B 107.4 . . ? 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 . . ? 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 C24 N1 C1 C2 -179.8(5) . . . . ? C24 N1 C1 C6 0.0(5) . . . . ? N1 C1 C2 C3 -179.8(5) . . . . ? C6 C1 C2 C3 0.4(8) . . . . ? C1 C2 C3 C4 -1.1(9) . . . . ? C2 C3 C4 C5 1.6(9) . . . . ? C3 C4 C5 C6 -1.3(9) . . . . ? C4 C5 C6 C1 0.6(8) . . . . ? C4 C5 C6 C7 179.3(6) . . . . ? C2 C1 C6 C5 -0.1(8) . . . . ? N1 C1 C6 C5 -180.0(4) . . . . ? C2 C1 C6 C7 -179.2(5) . . . . ? N1 C1 C6 C7 0.9(5) . . . . ? C5 C6 C7 C24 179.6(6) . . . . ? C1 C6 C7 C24 -1.5(5) . . . . ? C5 C6 C7 C8 -2.4(10) . . . . ? C1 C6 C7 C8 176.5(5) . . . . ? C9 N2 C8 C7 -179.1(4) . . . . ? C9 N2 C8 C15 -0.1(7) . . . . ? C24 C7 C8 N2 177.7(4) . . . . ? C6 C7 C8 N2 0.0(8) . . . . ? C24 C7 C8 C15 -1.3(7) . . . . ? C6 C7 C8 C15 -179.0(5) . . . . ? C8 N2 C9 C10 177.9(4) . . . . ? C8 N2 C9 C14 -1.6(7) . . . . ? N2 C9 C10 C11 178.4(5) . . . . ? C14 C9 C10 C11 -2.1(8) . . . . ? C9 C10 C11 C12 0.7(9) . . . . ? C10 C11 C12 C13 -0.3(9) . . . . ? C11 C12 C13 C14 1.4(9) . . . . ? C15 N3 C14 C9 0.1(7) . . . . ? C15 N3 C14 C13 179.3(5) . . . . ? N2 C9 C14 N3 1.8(7) . . . . ? C10 C9 C14 N3 -177.7(5) . . . . ? N2 C9 C14 C13 -177.4(5) . . . . ? C10 C9 C14 C13 3.1(7) . . . . ? C12 C13 C14 N3 178.0(5) . . . . ? C12 C13 C14 C9 -2.8(8) . . . . ? C14 N3 C15 C16 177.7(4) . . . . ? C14 N3 C15 C8 -1.9(7) . . . . ? N2 C8 C15 N3 2.0(7) . . . . ? C7 C8 C15 N3 -179.0(4) . . . . ? N2 C8 C15 C16 -177.6(4) . . . . ? C7 C8 C15 C16 1.4(7) . . . . ? N3 C15 C16 C23 178.7(4) . . . . ? C8 C15 C16 C23 -1.7(7) . . . . ? N3 C15 C16 C17 -2.9(8) . . . . ? C8 C15 C16 C17 176.7(5) . . . . ? C23 C16 C17 C18 178.7(6) . . . . ? C15 C16 C17 C18 0.2(10) . . . . ? C23 C16 C17 C22 -1.9(5) . . . . ? C15 C16 C17 C22 179.6(5) . . . . ? C22 C17 C18 C19 0.6(7) . . . . ? C16 C17 C18 C19 -180.0(5) . . . . ? C17 C18 C19 C20 -0.9(8) . . . . ? C18 C19 C20 C21 0.8(8) . . . . ? C19 C20 C21 C22 -0.3(8) . . . . ? C20 C21 C22 N4 179.3(5) . . . . ? C20 C21 C22 C17 0.0(8) . . . . ? C23 N4 C22 C21 -178.8(5) . . . . ? C23 N4 C22 C17 0.6(6) . . . . ? C18 C17 C22 C21 -0.2(8) . . . . ? C16 C17 C22 C21 -179.7(5) . . . . ? C18 C17 C22 N4 -179.6(4) . . . . ? C16 C17 C22 N4 0.9(6) . . . . ? C22 N4 C23 C16 -1.8(6) . . . . ? C22 N4 C23 C24 177.4(5) . . . . ? C17 C16 C23 N4 2.4(6) . . . . ? C15 C16 C23 N4 -178.9(4) . . . . ? C17 C16 C23 C24 -176.9(4) . . . . ? C15 C16 C23 C24 1.8(7) . . . . ? C1 N1 C24 C23 -179.1(5) . . . . ? C1 N1 C24 C7 -1.0(6) . . . . ? N4 C23 C24 N1 -3.0(9) . . . . ? C16 C23 C24 N1 176.1(5) . . . . ? N4 C23 C24 C7 179.1(5) . . . . ? C16 C23 C24 C7 -1.7(7) . . . . ? C8 C7 C24 N1 -176.8(4) . . . . ? C6 C7 C24 N1 1.6(6) . . . . ? C8 C7 C24 C23 1.4(7) . . . . ? C6 C7 C24 C23 179.8(4) . . . . ? C37 N5 C25 C26 60.0(6) . . . . ? C33 N5 C25 C26 -178.5(5) . . . . ? C29 N5 C25 C26 -58.4(6) . . . . ? N5 C25 C26 C27 173.9(5) . . . . ? C25 C26 C27 C28 173.8(5) . . . . ? C37 N5 C29 C30 176.3(4) . . . . ? C33 N5 C29 C30 54.4(5) . . . . ? C25 N5 C29 C30 -63.4(5) . . . . ? N5 C29 C30 C31 166.0(4) . . . . ? C29 C30 C31 C32 176.9(5) . . . . ? C37 N5 C33 C34 -55.3(6) . . . . ? C25 N5 C33 C34 -175.8(4) . . . . ? C29 N5 C33 C34 63.8(6) . . . . ? N5 C33 C34 C35 -174.0(5) . . . . ? C33 C34 C35 C36 74.4(6) . . . . ? C33 N5 C37 C38 -59.3(5) . . . . ? C25 N5 C37 C38 59.1(5) . . . . ? C29 N5 C37 C38 179.7(4) . . . . ? N5 C37 C38 C39 174.4(4) . . . . ? C37 C38 C39 C40 179.9(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.595 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.051 # ---------------Attachment 'DIPZ-AcO.CIF' data_r81230c1 _database_code_depnum_ccdc_archive 'CCDC 748210' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DIPZ+OAc _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H53 N5 O2' _chemical_formula_weight 659.89 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 21.802(4) _cell_length_b 8.4417(17) _cell_length_c 22.560(5) _cell_angle_alpha 90.00 _cell_angle_beta 118.82(3) _cell_angle_gamma 90.00 _cell_volume 3637.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7846 _cell_measurement_theta_min 1.807 _cell_measurement_theta_max 27.876 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9794 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23862 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6398 _reflns_number_gt 4844 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The restraints are made to refine the bond length of N-H in the two indole groups in DIPZ. The length is fixed at 0.90 as the theoretical bond length of N-H. ; _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^)+(0.0777P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6398 _refine_ls_number_parameters 455 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.014 _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 N1 N 0.34578(7) 0.32117(19) 0.50554(7) 0.0286(4) Uani 1 1 d D . . N2 N 0.15863(7) 0.10027(18) 0.31435(6) 0.0260(3) Uani 1 1 d . . . N3 N 0.07622(7) 0.07622(18) 0.38134(6) 0.0280(4) Uani 1 1 d . . . N4 N 0.25688(7) 0.28630(19) 0.58061(6) 0.0285(4) Uani 1 1 d D . . C1 C 0.36306(8) 0.3098(2) 0.45419(8) 0.0257(4) Uani 1 1 d . . . C2 C 0.42416(9) 0.3561(2) 0.45405(8) 0.0315(4) Uani 1 1 d . . . H2 H 0.4611 0.4006 0.4923 0.038 Uiso 1 1 calc R . . C3 C 0.42840(9) 0.3341(2) 0.39539(8) 0.0323(5) Uani 1 1 d . . . H3 H 0.4689 0.3641 0.3942 0.039 Uiso 1 1 calc R . . C4 C 0.37269(9) 0.2673(2) 0.33764(8) 0.0307(4) Uani 1 1 d . . . H4 H 0.3766 0.2541 0.2987 0.037 Uiso 1 1 calc R . . C5 C 0.31202(9) 0.2208(2) 0.33785(8) 0.0264(4) Uani 1 1 d . . . H5 H 0.2753 0.1764 0.2993 0.032 Uiso 1 1 calc R . . C6 C 0.30631(8) 0.2412(2) 0.39653(8) 0.0239(4) Uani 1 1 d . . . C7 C 0.25266(8) 0.2103(2) 0.41482(7) 0.0238(4) Uani 1 1 d . . . C8 C 0.18353(8) 0.1460(2) 0.37860(7) 0.0238(4) Uani 1 1 d . . . C9 C 0.09180(8) 0.0433(2) 0.28243(8) 0.0258(4) Uani 1 1 d . . . C10 C 0.06215(9) -0.0050(2) 0.21383(8) 0.0296(4) Uani 1 1 d . . . H10 H 0.0886 0.0015 0.1917 0.036 Uiso 1 1 calc R . . C11 C -0.00434(9) -0.0604(2) 0.18032(8) 0.0352(5) Uani 1 1 d . . . H11 H -0.0231 -0.0924 0.1355 0.042 Uiso 1 1 calc R . . C12 C -0.04529(9) -0.0698(2) 0.21333(8) 0.0368(5) Uani 1 1 d . . . H12 H -0.0911 -0.1067 0.1898 0.044 Uiso 1 1 calc R . . C13 C -0.01852(9) -0.0256(2) 0.27906(9) 0.0340(5) Uani 1 1 d . . . H13 H -0.0459 -0.0333 0.3002 0.041 Uiso 1 1 calc R . . C14 C 0.05098(9) 0.0322(2) 0.31562(8) 0.0272(4) Uani 1 1 d . . . C15 C 0.14161(8) 0.1333(2) 0.41282(7) 0.0241(4) Uani 1 1 d . . . C16 C 0.17132(8) 0.1852(2) 0.48151(8) 0.0249(4) Uani 1 1 d . . . C17 C 0.14626(9) 0.1827(2) 0.53011(8) 0.0254(4) Uani 1 1 d . . . C18 C 0.08410(9) 0.1370(2) 0.52916(8) 0.0287(4) Uani 1 1 d . . . H18 H 0.0469 0.0975 0.4897 0.034 Uiso 1 1 calc R . . C19 C 0.07865(10) 0.1513(2) 0.58761(8) 0.0320(4) Uani 1 1 d . . . H19 H 0.0370 0.1235 0.5869 0.038 Uiso 1 1 calc R . . C20 C 0.13475(10) 0.2068(2) 0.64773(8) 0.0321(5) Uani 1 1 d . . . H20 H 0.1304 0.2118 0.6867 0.038 Uiso 1 1 calc R . . C21 C 0.19655(9) 0.2543(2) 0.65002(8) 0.0311(4) Uani 1 1 d . . . H21 H 0.2337 0.2918 0.6900 0.037 Uiso 1 1 calc R . . C22 C 0.20162(9) 0.2443(2) 0.59110(8) 0.0262(4) Uani 1 1 d . . . C23 C 0.23898(8) 0.2484(2) 0.51504(8) 0.0258(4) Uani 1 1 d . . . C24 C 0.27956(8) 0.2619(2) 0.48157(8) 0.0244(4) Uani 1 1 d . . . N5 N 0.27390(7) 0.73078(18) 0.22798(7) 0.0286(4) Uani 1 1 d . . . C25 C 0.29692(10) 0.6197(2) 0.18927(9) 0.0339(5) Uani 1 1 d . . . H25A H 0.3323 0.5488 0.2214 0.041 Uiso 1 1 calc R . . H25B H 0.2571 0.5555 0.1591 0.041 Uiso 1 1 calc R . . C26 C 0.32616(10) 0.6998(2) 0.14777(9) 0.0353(5) Uani 1 1 d . . . H26A H 0.2949 0.7840 0.1208 0.042 Uiso 1 1 calc R . . H26B H 0.3714 0.7464 0.1778 0.042 Uiso 1 1 calc R . . C27 C 0.33410(10) 0.5800(3) 0.10174(9) 0.0404(5) Uani 1 1 d . . . H27A H 0.3612 0.4906 0.1286 0.048 Uiso 1 1 calc R . . H27B H 0.2882 0.5411 0.0692 0.048 Uiso 1 1 calc R . . C28 C 0.36966(12) 0.6485(3) 0.06395(10) 0.0567(7) Uani 1 1 d . . . H28A H 0.3424 0.7352 0.0362 0.085 Uiso 1 1 calc R . . H28B H 0.3735 0.5680 0.0358 0.085 Uiso 1 1 calc R . . H28C H 0.4155 0.6855 0.0958 0.085 Uiso 1 1 calc R . . C29 C 0.21385(9) 0.8360(2) 0.17983(8) 0.0318(4) Uani 1 1 d . . . H29A H 0.2291 0.8950 0.1524 0.038 Uiso 1 1 calc R . . H29B H 0.2043 0.9123 0.2065 0.038 Uiso 1 1 calc R . . C30 C 0.14579(10) 0.7518(3) 0.13277(9) 0.0391(5) Uani 1 1 d . . . H30A H 0.1220 0.7216 0.1579 0.047 Uiso 1 1 calc R . . H30B H 0.1562 0.6559 0.1156 0.047 Uiso 1 1 calc R . . C31 C 0.09767(10) 0.8577(3) 0.07337(9) 0.0410(5) Uani 1 1 d . . . H31A H 0.0503 0.8168 0.0537 0.049 Uiso 1 1 calc R . . H31B H 0.0976 0.9633 0.0903 0.049 Uiso 1 1 calc R . . C32 C 0.11867(12) 0.8689(3) 0.01857(9) 0.0558(7) Uani 1 1 d . . . H32A H 0.1649 0.9126 0.0372 0.084 Uiso 1 1 calc R . . H32B H 0.0863 0.9361 -0.0172 0.084 Uiso 1 1 calc R . . H32C H 0.1181 0.7651 0.0009 0.084 Uiso 1 1 calc R . . C33 C 0.25027(10) 0.6280(2) 0.26877(9) 0.0333(4) Uani 1 1 d . . . H33A H 0.2152 0.5543 0.2381 0.040 Uiso 1 1 calc R . . H33B H 0.2900 0.5661 0.3007 0.040 Uiso 1 1 calc R . . C34 C 0.22012(10) 0.7163(2) 0.30779(9) 0.0354(5) Uani 1 1 d . . . H34A H 0.2461 0.8136 0.3262 0.043 Uiso 1 1 calc R . . H34B H 0.1717 0.7441 0.2774 0.043 Uiso 1 1 calc R . . C35 C 0.22402(11) 0.6149(3) 0.36474(10) 0.0446(5) Uani 1 1 d . . . H35A H 0.2728 0.5943 0.3967 0.054 Uiso 1 1 calc R . . H35B H 0.2016 0.5140 0.3465 0.054 Uiso 1 1 calc R . . C36 C 0.18941(13) 0.6915(3) 0.40179(11) 0.0593(7) Uani 1 1 d . . . H36A H 0.2126 0.7896 0.4215 0.089 Uiso 1 1 calc R . . H36B H 0.1926 0.6218 0.4368 0.089 Uiso 1 1 calc R . . H36C H 0.1411 0.7119 0.3705 0.089 Uiso 1 1 calc R . . C37 C 0.33404(9) 0.8377(2) 0.27455(8) 0.0288(4) Uani 1 1 d . . . H37A H 0.3189 0.9010 0.3010 0.035 Uiso 1 1 calc R . . H37B H 0.3442 0.9098 0.2469 0.035 Uiso 1 1 calc R . . C38 C 0.40155(9) 0.7525(2) 0.32299(8) 0.0339(5) Uani 1 1 d . . . H38A H 0.4276 0.7263 0.2995 0.041 Uiso 1 1 calc R . . H38B H 0.3903 0.6544 0.3380 0.041 Uiso 1 1 calc R . . C39 C 0.44686(10) 0.8559(3) 0.38441(8) 0.0367(5) Uani 1 1 d . . . H39A H 0.4939 0.8127 0.4075 0.044 Uiso 1 1 calc R . . H39B H 0.4496 0.9616 0.3690 0.044 Uiso 1 1 calc R . . C40 C 0.41879(10) 0.8669(3) 0.43411(9) 0.0454(6) Uani 1 1 d . . . H40A H 0.3736 0.9164 0.4125 0.068 Uiso 1 1 calc R . . H40B H 0.4503 0.9287 0.4725 0.068 Uiso 1 1 calc R . . H40C H 0.4148 0.7624 0.4487 0.068 Uiso 1 1 calc R . . O1 O 0.37515(6) 0.10245(18) 0.18413(6) 0.0404(4) Uani 1 1 d . . . O2 O 0.43592(6) 0.0691(2) 0.12854(6) 0.0493(4) Uani 1 1 d . . . C41 C 0.42900(9) 0.0634(2) 0.18066(9) 0.0350(5) Uani 1 1 d . . . C42 C 0.49160(9) 0.0032(3) 0.24525(9) 0.0497(6) Uani 1 1 d . . . H42A H 0.5256 -0.0411 0.2345 0.075 Uiso 1 1 calc R . . H42B H 0.4764 -0.0768 0.2655 0.075 Uiso 1 1 calc R . . H42C H 0.5122 0.0895 0.2764 0.075 Uiso 1 1 calc R . . H1A H 0.3732(8) 0.358(2) 0.5490(6) 0.045(6) Uiso 1 1 d D . . H4A H 0.3006(7) 0.323(2) 0.6131(8) 0.052(6) Uiso 1 1 d 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 N1 0.0266(8) 0.0333(10) 0.0238(8) -0.0025(6) 0.0105(6) -0.0012(7) N2 0.0278(7) 0.0259(9) 0.0223(7) 0.0012(6) 0.0105(6) 0.0012(6) N3 0.0290(8) 0.0287(10) 0.0240(7) 0.0010(6) 0.0109(6) -0.0017(7) N4 0.0310(8) 0.0311(10) 0.0203(8) -0.0017(6) 0.0099(7) 0.0006(7) C1 0.0284(9) 0.0238(11) 0.0238(9) 0.0013(7) 0.0117(7) 0.0037(8) C2 0.0276(9) 0.0321(12) 0.0305(9) 0.0012(8) 0.0105(8) -0.0006(8) C3 0.0296(10) 0.0321(12) 0.0386(10) 0.0060(8) 0.0190(8) 0.0038(8) C4 0.0378(10) 0.0294(12) 0.0287(9) 0.0032(7) 0.0192(8) 0.0036(8) C5 0.0302(9) 0.0264(11) 0.0221(9) 0.0026(7) 0.0124(7) 0.0037(8) C6 0.0248(9) 0.0213(10) 0.0233(9) 0.0044(7) 0.0097(7) 0.0050(7) C7 0.0270(9) 0.0211(11) 0.0212(8) 0.0029(6) 0.0100(7) 0.0035(7) C8 0.0269(9) 0.0232(11) 0.0174(8) 0.0028(6) 0.0076(7) 0.0026(7) C9 0.0300(9) 0.0225(11) 0.0230(8) 0.0029(7) 0.0113(7) -0.0009(8) C10 0.0346(10) 0.0298(12) 0.0240(9) -0.0009(7) 0.0137(8) -0.0030(8) C11 0.0402(10) 0.0364(13) 0.0253(9) -0.0038(8) 0.0129(8) -0.0091(9) C12 0.0348(10) 0.0402(14) 0.0299(10) -0.0039(8) 0.0113(8) -0.0120(9) C13 0.0340(10) 0.0371(13) 0.0331(10) 0.0015(8) 0.0179(8) -0.0073(9) C14 0.0311(9) 0.0247(11) 0.0231(9) 0.0029(7) 0.0110(7) -0.0013(8) C15 0.0286(9) 0.0215(10) 0.0212(8) 0.0022(6) 0.0112(7) 0.0024(7) C16 0.0279(9) 0.0246(11) 0.0214(8) 0.0018(7) 0.0114(7) 0.0039(8) C17 0.0309(9) 0.0219(11) 0.0237(9) 0.0026(7) 0.0134(7) 0.0043(8) C18 0.0345(10) 0.0272(11) 0.0260(9) 0.0024(7) 0.0159(8) 0.0034(8) C19 0.0408(11) 0.0291(12) 0.0353(10) 0.0029(8) 0.0256(9) 0.0035(9) C20 0.0472(11) 0.0275(12) 0.0293(10) 0.0019(7) 0.0247(9) 0.0054(9) C21 0.0425(11) 0.0274(12) 0.0234(9) -0.0007(7) 0.0159(8) 0.0041(9) C22 0.0318(9) 0.0236(11) 0.0233(9) 0.0030(7) 0.0133(7) 0.0045(8) C23 0.0306(9) 0.0244(11) 0.0203(8) 0.0006(7) 0.0105(7) 0.0028(8) C24 0.0243(9) 0.0238(11) 0.0229(8) 0.0022(7) 0.0096(7) 0.0016(8) N5 0.0387(8) 0.0215(9) 0.0313(8) 0.0006(6) 0.0213(7) -0.0028(7) C25 0.0433(11) 0.0267(12) 0.0387(10) -0.0058(8) 0.0253(9) -0.0010(9) C26 0.0450(11) 0.0313(13) 0.0352(10) -0.0037(8) 0.0239(9) -0.0038(9) C27 0.0478(11) 0.0415(14) 0.0345(10) -0.0114(8) 0.0220(9) -0.0088(10) C28 0.0687(15) 0.0680(19) 0.0502(13) -0.0121(11) 0.0420(12) -0.0114(13) C29 0.0393(10) 0.0263(11) 0.0301(9) 0.0007(7) 0.0171(8) -0.0008(8) C30 0.0428(11) 0.0374(14) 0.0362(10) -0.0039(8) 0.0183(9) -0.0091(10) C31 0.0399(11) 0.0483(15) 0.0299(10) -0.0064(9) 0.0129(8) -0.0090(10) C32 0.0679(15) 0.0651(19) 0.0344(11) -0.0057(10) 0.0245(11) -0.0075(13) C33 0.0439(11) 0.0242(12) 0.0408(10) 0.0054(8) 0.0275(9) -0.0004(9) C34 0.0451(11) 0.0311(13) 0.0392(10) 0.0049(8) 0.0275(9) 0.0016(9) C35 0.0507(12) 0.0437(15) 0.0528(12) 0.0173(10) 0.0356(10) 0.0131(10) C36 0.0765(16) 0.0636(19) 0.0616(14) 0.0265(12) 0.0523(13) 0.0238(14) C37 0.0373(10) 0.0232(11) 0.0294(9) -0.0031(7) 0.0188(8) -0.0043(8) C38 0.0423(11) 0.0281(12) 0.0342(10) 0.0028(8) 0.0207(9) 0.0031(9) C39 0.0369(10) 0.0393(14) 0.0341(10) 0.0033(8) 0.0172(8) 0.0017(9) C40 0.0431(12) 0.0574(16) 0.0333(10) 0.0000(9) 0.0165(9) 0.0053(11) O1 0.0371(7) 0.0517(10) 0.0303(7) 0.0097(6) 0.0147(6) 0.0039(7) O2 0.0372(7) 0.0759(12) 0.0321(7) 0.0195(7) 0.0146(6) 0.0080(7) C41 0.0308(10) 0.0385(13) 0.0295(10) 0.0085(8) 0.0095(8) -0.0070(9) C42 0.0339(11) 0.0715(18) 0.0347(11) 0.0196(10) 0.0092(9) -0.0044(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 N1 C24 1.369(2) . ? N1 C1 1.384(2) . ? N1 H1A 0.922(9) . ? N2 C8 1.336(2) . ? N2 C9 1.364(2) . ? N3 C15 1.339(2) . ? N3 C14 1.361(2) . ? N4 C23 1.373(2) . ? N4 C22 1.381(2) . ? N4 H4A 0.930(9) . ? C1 C2 1.390(2) . ? C1 C6 1.416(2) . ? C2 C3 1.383(2) . ? C2 H2 0.9300 . ? C3 C4 1.402(2) . ? C3 H3 0.9300 . ? C4 C5 1.382(2) . ? C4 H4 0.9300 . ? C5 C6 1.399(2) . ? C5 H5 0.9300 . ? C6 C7 1.439(2) . ? C7 C24 1.396(2) . ? C7 C8 1.431(2) . ? C8 C15 1.457(2) . ? C9 C14 1.416(2) . ? C9 C10 1.419(2) . ? C10 C11 1.355(2) . ? C10 H10 0.9300 . ? C11 C12 1.414(3) . ? C11 H11 0.9300 . ? C12 C13 1.358(2) . ? C12 H12 0.9300 . ? C13 C14 1.417(2) . ? C13 H13 0.9300 . ? C15 C16 1.430(2) . ? C16 C23 1.399(2) . ? C16 C17 1.442(2) . ? C17 C18 1.399(2) . ? C17 C22 1.421(2) . ? C18 C19 1.385(2) . ? C18 H18 0.9300 . ? C19 C20 1.398(3) . ? C19 H19 0.9300 . ? C20 C21 1.383(3) . ? C20 H20 0.9300 . ? C21 C22 1.388(2) . ? C21 H21 0.9300 . ? C23 C24 1.418(2) . ? N5 C37 1.520(2) . ? N5 C29 1.521(2) . ? N5 C25 1.522(2) . ? N5 C33 1.524(2) . ? C25 C26 1.522(2) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.518(2) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.516(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.522(2) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.530(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.514(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.524(2) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.512(2) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.514(3) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C38 1.525(2) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.529(3) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.517(3) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? O1 C41 1.258(2) . ? O2 C41 1.257(2) . ? C41 C42 1.525(2) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 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 C24 N1 C1 107.74(14) . . ? C24 N1 H1A 124.2(12) . . ? C1 N1 H1A 128.0(12) . . ? C8 N2 C9 116.51(15) . . ? C15 N3 C14 116.36(15) . . ? C23 N4 C22 107.84(14) . . ? C23 N4 H4A 125.3(13) . . ? C22 N4 H4A 126.5(13) . . ? N1 C1 C2 129.09(15) . . ? N1 C1 C6 109.11(15) . . ? C2 C1 C6 121.79(16) . . ? C3 C2 C1 118.08(16) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 121.05(17) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.86(16) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.37(16) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 118.85(16) . . ? C5 C6 C7 134.79(15) . . ? C1 C6 C7 106.36(14) . . ? C24 C7 C8 120.91(15) . . ? C24 C7 C6 106.01(14) . . ? C8 C7 C6 133.07(14) . . ? N2 C8 C7 119.63(15) . . ? N2 C8 C15 121.53(15) . . ? C7 C8 C15 118.83(14) . . ? N2 C9 C14 121.86(14) . . ? N2 C9 C10 119.06(15) . . ? C14 C9 C10 119.07(15) . . ? C11 C10 C9 120.66(17) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.19(16) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.76(17) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 120.41(18) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? N3 C14 C9 122.08(15) . . ? N3 C14 C13 119.03(16) . . ? C9 C14 C13 118.89(15) . . ? N3 C15 C16 119.69(15) . . ? N3 C15 C8 121.65(14) . . ? C16 C15 C8 118.66(15) . . ? C23 C16 C15 120.76(16) . . ? C23 C16 C17 106.36(14) . . ? C15 C16 C17 132.84(16) . . ? C18 C17 C22 118.69(15) . . ? C18 C17 C16 135.37(15) . . ? C22 C17 C16 105.94(15) . . ? C19 C18 C17 119.23(16) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 121.08(17) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C21 C20 C19 120.95(16) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 118.20(16) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? N4 C22 C21 128.83(16) . . ? N4 C22 C17 109.38(14) . . ? C21 C22 C17 121.78(16) . . ? N4 C23 C16 110.44(15) . . ? N4 C23 C24 128.96(15) . . ? C16 C23 C24 120.58(14) . . ? N1 C24 C7 110.78(15) . . ? N1 C24 C23 128.97(15) . . ? C7 C24 C23 120.25(15) . . ? C37 N5 C29 107.80(14) . . ? C37 N5 C25 110.44(13) . . ? C29 N5 C25 111.02(13) . . ? C37 N5 C33 110.54(13) . . ? C29 N5 C33 109.82(14) . . ? C25 N5 C33 107.25(15) . . ? C26 C25 N5 115.56(16) . . ? C26 C25 H25A 108.4 . . ? N5 C25 H25A 108.4 . . ? C26 C25 H25B 108.4 . . ? N5 C25 H25B 108.4 . . ? H25A C25 H25B 107.5 . . ? C27 C26 C25 110.18(17) . . ? C27 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? C27 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? C28 C27 C26 112.86(18) . . ? C28 C27 H27A 109.0 . . ? C26 C27 H27A 109.0 . . ? C28 C27 H27B 109.0 . . ? C26 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N5 C29 C30 116.05(16) . . ? N5 C29 H29A 108.3 . . ? C30 C29 H29A 108.3 . . ? N5 C29 H29B 108.3 . . ? C30 C29 H29B 108.3 . . ? H29A C29 H29B 107.4 . . ? C29 C30 C31 111.35(17) . . ? C29 C30 H30A 109.4 . . ? C31 C30 H30A 109.4 . . ? C29 C30 H30B 109.4 . . ? C31 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C32 C31 C30 113.71(18) . . ? C32 C31 H31A 108.8 . . ? C30 C31 H31A 108.8 . . ? C32 C31 H31B 108.8 . . ? C30 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 N5 115.83(16) . . ? C34 C33 H33A 108.3 . . ? N5 C33 H33A 108.3 . . ? C34 C33 H33B 108.3 . . ? N5 C33 H33B 108.3 . . ? H33A C33 H33B 107.4 . . ? C35 C34 C33 110.54(17) . . ? C35 C34 H34A 109.5 . . ? C33 C34 H34A 109.5 . . ? C35 C34 H34B 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? C34 C35 C36 112.86(18) . . ? C34 C35 H35A 109.0 . . ? C36 C35 H35A 109.0 . . ? C34 C35 H35B 109.0 . . ? C36 C35 H35B 109.0 . . ? H35A C35 H35B 107.8 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N5 C37 C38 115.36(15) . . ? N5 C37 H37A 108.4 . . ? C38 C37 H37A 108.4 . . ? N5 C37 H37B 108.4 . . ? C38 C37 H37B 108.4 . . ? H37A C37 H37B 107.5 . . ? C37 C38 C39 111.03(16) . . ? C37 C38 H38A 109.4 . . ? C39 C38 H38A 109.4 . . ? C37 C38 H38B 109.4 . . ? C39 C38 H38B 109.4 . . ? H38A C38 H38B 108.0 . . ? C40 C39 C38 112.95(16) . . ? C40 C39 H39A 109.0 . . ? C38 C39 H39A 109.0 . . ? C40 C39 H39B 109.0 . . ? C38 C39 H39B 109.0 . . ? H39A C39 H39B 107.8 . . ? 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 . . ? O2 C41 O1 125.79(16) . . ? O2 C41 C42 116.81(17) . . ? O1 C41 C42 117.40(17) . . ? 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 . . ? 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 C24 N1 C1 C2 179.17(18) . . . . ? C24 N1 C1 C6 -0.1(2) . . . . ? N1 C1 C2 C3 -178.99(18) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C7 178.90(18) . . . . ? N1 C1 C6 C5 178.94(15) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? N1 C1 C6 C7 -0.06(19) . . . . ? C2 C1 C6 C7 -179.44(16) . . . . ? C5 C6 C7 C24 -178.53(19) . . . . ? C1 C6 C7 C24 0.24(18) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C1 C6 C7 C8 178.61(18) . . . . ? C9 N2 C8 C7 -178.60(15) . . . . ? C9 N2 C8 C15 0.8(2) . . . . ? C24 C7 C8 N2 178.75(16) . . . . ? C6 C7 C8 N2 0.6(3) . . . . ? C24 C7 C8 C15 -0.7(2) . . . . ? C6 C7 C8 C15 -178.86(18) . . . . ? C8 N2 C9 C14 -0.3(2) . . . . ? C8 N2 C9 C10 179.10(16) . . . . ? N2 C9 C10 C11 -179.23(17) . . . . ? C14 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C15 N3 C14 C9 1.1(3) . . . . ? C15 N3 C14 C13 -178.50(16) . . . . ? N2 C9 C14 N3 -0.7(3) . . . . ? C10 C9 C14 N3 179.91(17) . . . . ? N2 C9 C14 C13 178.92(17) . . . . ? C10 C9 C14 C13 -0.5(3) . . . . ? C12 C13 C14 N3 179.72(18) . . . . ? C12 C13 C14 C9 0.1(3) . . . . ? C14 N3 C15 C16 178.70(16) . . . . ? C14 N3 C15 C8 -0.6(2) . . . . ? N2 C8 C15 N3 -0.4(3) . . . . ? C7 C8 C15 N3 179.04(16) . . . . ? N2 C8 C15 C16 -179.67(16) . . . . ? C7 C8 C15 C16 -0.2(2) . . . . ? N3 C15 C16 C23 -178.62(16) . . . . ? C8 C15 C16 C23 0.7(3) . . . . ? N3 C15 C16 C17 4.0(3) . . . . ? C8 C15 C16 C17 -176.70(17) . . . . ? C23 C16 C17 C18 179.0(2) . . . . ? C15 C16 C17 C18 -3.3(4) . . . . ? C23 C16 C17 C22 -0.55(19) . . . . ? C15 C16 C17 C22 177.10(18) . . . . ? C22 C17 C18 C19 -0.8(3) . . . . ? C16 C17 C18 C19 179.69(19) . . . . ? C17 C18 C19 C20 -1.6(3) . . . . ? C18 C19 C20 C21 2.3(3) . . . . ? C19 C20 C21 C22 -0.4(3) . . . . ? C23 N4 C22 C21 177.30(18) . . . . ? C23 N4 C22 C17 -1.8(2) . . . . ? C20 C21 C22 N4 178.98(17) . . . . ? C20 C21 C22 C17 -2.0(3) . . . . ? C18 C17 C22 N4 -178.19(15) . . . . ? C16 C17 C22 N4 1.5(2) . . . . ? C18 C17 C22 C21 2.6(3) . . . . ? C16 C17 C22 C21 -177.74(16) . . . . ? C22 N4 C23 C16 1.5(2) . . . . ? C22 N4 C23 C24 -176.71(17) . . . . ? C15 C16 C23 N4 -178.56(16) . . . . ? C17 C16 C23 N4 -0.6(2) . . . . ? C15 C16 C23 C24 -0.2(3) . . . . ? C17 C16 C23 C24 177.81(16) . . . . ? C1 N1 C24 C7 0.3(2) . . . . ? C1 N1 C24 C23 -179.86(17) . . . . ? C8 C7 C24 N1 -178.95(15) . . . . ? C6 C7 C24 N1 -0.35(19) . . . . ? C8 C7 C24 C23 1.2(3) . . . . ? C6 C7 C24 C23 179.81(15) . . . . ? N4 C23 C24 N1 -2.5(3) . . . . ? C16 C23 C24 N1 179.42(17) . . . . ? N4 C23 C24 C7 177.28(17) . . . . ? C16 C23 C24 C7 -0.8(3) . . . . ? C37 N5 C25 C26 -56.48(19) . . . . ? C29 N5 C25 C26 63.03(19) . . . . ? C33 N5 C25 C26 -177.00(15) . . . . ? N5 C25 C26 C27 -169.29(15) . . . . ? C25 C26 C27 C28 -174.37(17) . . . . ? C37 N5 C29 C30 -174.76(15) . . . . ? C25 N5 C29 C30 64.2(2) . . . . ? C33 N5 C29 C30 -54.27(19) . . . . ? N5 C29 C30 C31 -162.51(15) . . . . ? C29 C30 C31 C32 77.6(2) . . . . ? C37 N5 C33 C34 63.65(19) . . . . ? C29 N5 C33 C34 -55.16(19) . . . . ? C25 N5 C33 C34 -175.90(15) . . . . ? N5 C33 C34 C35 -158.82(16) . . . . ? C33 C34 C35 C36 -175.34(18) . . . . ? C29 N5 C37 C38 -175.23(14) . . . . ? C25 N5 C37 C38 -53.80(19) . . . . ? C33 N5 C37 C38 64.74(19) . . . . ? N5 C37 C38 C39 -157.11(15) . . . . ? C37 C38 C39 C40 74.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.170 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.048 # ---------------Attachment 'DIPZ-SiF6.CIF' data_070530c _database_code_depnum_ccdc_archive 'CCDC 748211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common DIPZ+SiF6 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C80 H100 F6 N10 Si' _chemical_formula_weight 1343.79 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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 9.5475(19) _cell_length_b 21.996(5) _cell_length_c 17.778(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.892(4) _cell_angle_gamma 90.00 _cell_volume 3706.5(13) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3584 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 24.36 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1436 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9790 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18786 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6538 _reflns_number_gt 3421 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The restraints are made to refine the bond length of N-H in the two indole groups in DIPZ. The length is fixed at 0.90 as the theoretical bond length of N-H. ; _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^)+(0.0560P)^2^+1.2127P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6538 _refine_ls_number_parameters 451 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1230 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 N1 N -0.0700(2) 0.26473(10) 0.24345(13) 0.0466(6) Uani 1 1 d . . . N2 N -0.0647(2) 0.36269(10) 0.13677(13) 0.0468(6) Uani 1 1 d . . . N3 N 0.2657(3) 0.36096(11) 0.41899(14) 0.0487(6) Uani 1 1 d D . . N4 N 0.2670(2) 0.47155(11) 0.30285(14) 0.0453(6) Uani 1 1 d D . . C1 C -0.1522(3) 0.26387(13) 0.17438(17) 0.0457(7) Uani 1 1 d . . . C2 C -0.2395(3) 0.21237(14) 0.15443(18) 0.0597(9) Uani 1 1 d . . . H2 H -0.2403 0.1802 0.1883 0.072 Uiso 1 1 calc R . . C3 C -0.3222(3) 0.20966(17) 0.0861(2) 0.0683(10) Uani 1 1 d . . . H3 H -0.3769 0.1754 0.0734 0.082 Uiso 1 1 calc R . . C4 C -0.3244(3) 0.25880(18) 0.0350(2) 0.0733(10) Uani 1 1 d . . . H4 H -0.3826 0.2571 -0.0108 0.088 Uiso 1 1 calc R . . C5 C -0.2413(3) 0.30934(16) 0.05214(18) 0.0652(9) Uani 1 1 d . . . H5 H -0.2441 0.3414 0.0179 0.078 Uiso 1 1 calc R . . C6 C -0.1509(3) 0.31292(14) 0.12200(16) 0.0458(7) Uani 1 1 d . . . C7 C 0.0183(3) 0.36307(12) 0.20354(15) 0.0405(7) Uani 1 1 d . . . C8 C 0.0133(3) 0.31375(12) 0.25889(15) 0.0394(7) Uani 1 1 d . . . C9 C 0.1011(3) 0.31817(12) 0.33067(15) 0.0412(7) Uani 1 1 d . . . C10 C 0.1206(3) 0.27793(13) 0.39642(15) 0.0434(7) Uani 1 1 d . . . C11 C 0.0600(3) 0.22239(13) 0.41640(17) 0.0516(8) Uani 1 1 d . . . H11 H -0.0085 0.2032 0.3830 0.062 Uiso 1 1 calc R . . C12 C 0.1045(3) 0.19713(15) 0.48657(18) 0.0620(9) Uani 1 1 d . . . H12 H 0.0642 0.1609 0.5003 0.074 Uiso 1 1 calc R . . C13 C 0.2092(4) 0.22504(15) 0.53756(18) 0.0655(9) Uani 1 1 d . . . H13 H 0.2376 0.2067 0.5840 0.079 Uiso 1 1 calc R . . C14 C 0.2709(3) 0.27948(15) 0.51975(17) 0.0568(8) Uani 1 1 d . . . H14 H 0.3408 0.2977 0.5533 0.068 Uiso 1 1 calc R . . C15 C 0.2246(3) 0.30616(13) 0.44956(16) 0.0448(7) Uani 1 1 d . . . C16 C 0.1905(3) 0.36828(13) 0.34785(15) 0.0411(7) Uani 1 1 d . . . C17 C 0.1937(3) 0.41704(12) 0.29512(15) 0.0408(7) Uani 1 1 d . . . C18 C 0.2354(3) 0.50492(13) 0.23621(16) 0.0409(7) Uani 1 1 d . . . C19 C 0.2822(3) 0.56289(14) 0.21835(18) 0.0522(8) Uani 1 1 d . . . H19 H 0.3433 0.5850 0.2528 0.063 Uiso 1 1 calc R . . C20 C 0.2339(3) 0.58625(14) 0.14725(19) 0.0598(9) Uani 1 1 d . . . H20 H 0.2631 0.6247 0.1339 0.072 Uiso 1 1 calc R . . C21 C 0.1414(3) 0.55274(15) 0.09491(19) 0.0616(9) Uani 1 1 d . . . H21 H 0.1114 0.5694 0.0476 0.074 Uiso 1 1 calc R . . C22 C 0.0942(3) 0.49525(13) 0.11286(17) 0.0489(8) Uani 1 1 d . . . H22 H 0.0334 0.4735 0.0779 0.059 Uiso 1 1 calc R . . C23 C 0.1403(3) 0.47038(12) 0.18501(16) 0.0411(7) Uani 1 1 d . . . C24 C 0.1120(3) 0.41419(12) 0.22378(15) 0.0391(7) Uani 1 1 d . . . N5 N 0.7707(2) 0.57009(10) 0.26674(12) 0.0444(6) Uani 1 1 d . . . C25 C 0.6900(3) 0.51363(12) 0.28939(16) 0.0470(7) Uani 1 1 d . . . H25A H 0.6724 0.5184 0.3417 0.056 Uiso 1 1 calc R . . H25B H 0.5991 0.5125 0.2585 0.056 Uiso 1 1 calc R . . C26 C 0.7629(3) 0.45233(14) 0.28175(19) 0.0609(9) Uani 1 1 d . . . H26A H 0.8007 0.4508 0.2335 0.073 Uiso 1 1 calc R . . H26B H 0.8411 0.4484 0.3217 0.073 Uiso 1 1 calc R . . C27 C 0.6607(4) 0.39937(14) 0.28668(19) 0.0654(9) Uani 1 1 d . . . H27A H 0.6109 0.4051 0.3306 0.078 Uiso 1 1 calc R . . H27B H 0.7142 0.3619 0.2939 0.078 Uiso 1 1 calc R . . C28 C 0.5527(4) 0.39327(16) 0.2158(2) 0.0848(12) Uani 1 1 d . . . H28A H 0.4987 0.4301 0.2086 0.127 Uiso 1 1 calc R . . H28B H 0.4906 0.3598 0.2222 0.127 Uiso 1 1 calc R . . H28C H 0.6012 0.3861 0.1724 0.127 Uiso 1 1 calc R . . C29 C 0.9181(3) 0.57400(15) 0.31266(16) 0.0517(8) Uani 1 1 d . . . H29A H 0.9690 0.5370 0.3040 0.062 Uiso 1 1 calc R . . H29B H 0.9687 0.6074 0.2928 0.062 Uiso 1 1 calc R . . C30 C 0.9220(3) 0.58286(15) 0.39798(16) 0.0559(8) Uani 1 1 d . . . H30A H 0.8614 0.5532 0.4182 0.067 Uiso 1 1 calc R . . H30B H 0.8875 0.6231 0.4084 0.067 Uiso 1 1 calc R . . C31 C 1.0733(3) 0.57545(16) 0.43632(18) 0.0642(9) Uani 1 1 d . . . H31A H 1.0989 0.5328 0.4358 0.077 Uiso 1 1 calc R . . H31B H 1.1365 0.5975 0.4073 0.077 Uiso 1 1 calc R . . C32 C 1.0939(4) 0.59817(19) 0.5175(2) 0.0886(12) Uani 1 1 d . . . H32A H 1.0787 0.6413 0.5181 0.133 Uiso 1 1 calc R . . H32B H 1.1882 0.5892 0.5398 0.133 Uiso 1 1 calc R . . H32C H 1.0277 0.5784 0.5460 0.133 Uiso 1 1 calc R . . C33 C 0.6804(3) 0.62519(12) 0.28177(16) 0.0464(7) Uani 1 1 d . . . H33A H 0.6634 0.6241 0.3345 0.056 Uiso 1 1 calc R . . H33B H 0.5897 0.6211 0.2511 0.056 Uiso 1 1 calc R . . C34 C 0.7414(3) 0.68774(13) 0.26578(17) 0.0549(8) Uani 1 1 d . . . H34A H 0.7812 0.6864 0.2181 0.066 Uiso 1 1 calc R . . H34B H 0.8167 0.6977 0.3055 0.066 Uiso 1 1 calc R . . C35 C 0.6268(3) 0.73747(14) 0.26189(18) 0.0610(9) Uani 1 1 d . . . H35A H 0.5750 0.7331 0.3053 0.073 Uiso 1 1 calc R . . H35B H 0.6724 0.7769 0.2656 0.073 Uiso 1 1 calc R . . C36 C 0.5222(4) 0.73580(16) 0.1898(2) 0.0814(11) Uani 1 1 d . . . H36A H 0.5721 0.7409 0.1465 0.122 Uiso 1 1 calc R . . H36B H 0.4548 0.7680 0.1913 0.122 Uiso 1 1 calc R . . H36C H 0.4741 0.6974 0.1865 0.122 Uiso 1 1 calc R . . C37 C 0.7952(3) 0.56724(15) 0.18312(15) 0.0532(8) Uani 1 1 d . . . H37A H 0.8583 0.6001 0.1735 0.064 Uiso 1 1 calc R . . H37B H 0.8434 0.5294 0.1749 0.064 Uiso 1 1 calc R . . C38 C 0.6647(3) 0.57124(17) 0.12465(17) 0.0675(10) Uani 1 1 d . . . H38A H 0.6267 0.6122 0.1239 0.081 Uiso 1 1 calc R . . H38B H 0.5929 0.5436 0.1385 0.081 Uiso 1 1 calc R . . C39 C 0.7025(4) 0.55486(18) 0.04601(17) 0.0740(10) Uani 1 1 d . . . H39A H 0.7908 0.5745 0.0386 0.089 Uiso 1 1 calc R . . H39B H 0.7167 0.5113 0.0435 0.089 Uiso 1 1 calc R . . C40 C 0.5900(4) 0.57372(19) -0.0177(2) 0.0981(14) Uani 1 1 d . . . H40A H 0.5008 0.5567 -0.0089 0.147 Uiso 1 1 calc R . . H40B H 0.6152 0.5592 -0.0651 0.147 Uiso 1 1 calc R . . H40C H 0.5829 0.6172 -0.0191 0.147 Uiso 1 1 calc R . . Si1 Si 0.5000 0.5000 0.5000 0.0505(3) Uani 1 2 d S . . F1 F 0.4387(2) 0.53232(10) 0.41509(11) 0.0863(6) Uani 1 1 d . . . F2 F 0.33523(18) 0.47951(10) 0.51238(11) 0.0861(7) Uani 1 1 d . . . F3 F 0.4828(2) 0.56673(9) 0.54480(11) 0.0873(7) Uani 1 1 d . . . H3A H 0.332(2) 0.3860(11) 0.4410(16) 0.076(11) Uiso 1 1 d D . . H4A H 0.324(3) 0.4838(14) 0.3439(12) 0.082(12) Uiso 1 1 d 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 N1 0.0446(14) 0.0457(15) 0.0483(16) -0.0082(12) 0.0006(12) -0.0026(12) N2 0.0444(14) 0.0509(16) 0.0436(15) -0.0076(12) -0.0005(12) -0.0022(12) N3 0.0518(16) 0.0491(17) 0.0430(16) -0.0091(13) -0.0031(13) -0.0047(13) N4 0.0443(15) 0.0453(16) 0.0460(17) -0.0076(13) 0.0036(13) -0.0041(12) C1 0.0380(16) 0.0482(19) 0.0508(19) -0.0101(16) 0.0049(14) 0.0008(14) C2 0.055(2) 0.055(2) 0.067(2) -0.0045(17) -0.0032(17) -0.0101(17) C3 0.050(2) 0.075(3) 0.077(3) -0.011(2) -0.0059(19) -0.0138(18) C4 0.057(2) 0.096(3) 0.061(2) -0.010(2) -0.0149(17) -0.015(2) C5 0.065(2) 0.077(3) 0.050(2) -0.0008(18) -0.0047(17) -0.0137(19) C6 0.0392(17) 0.056(2) 0.0421(18) -0.0113(16) 0.0029(14) -0.0027(15) C7 0.0378(16) 0.0450(18) 0.0388(17) -0.0098(14) 0.0052(14) 0.0030(14) C8 0.0384(16) 0.0406(17) 0.0396(17) -0.0090(14) 0.0068(13) 0.0027(14) C9 0.0426(17) 0.0424(17) 0.0386(17) -0.0052(14) 0.0049(13) -0.0033(14) C10 0.0450(17) 0.0445(18) 0.0410(17) -0.0065(14) 0.0062(14) 0.0019(14) C11 0.0579(19) 0.048(2) 0.049(2) -0.0064(16) 0.0088(16) -0.0067(16) C12 0.077(2) 0.056(2) 0.054(2) 0.0042(18) 0.0130(18) -0.0071(18) C13 0.082(3) 0.063(2) 0.049(2) 0.0065(18) 0.0010(19) 0.003(2) C14 0.060(2) 0.060(2) 0.047(2) -0.0044(16) -0.0028(16) 0.0015(17) C15 0.0485(18) 0.0472(19) 0.0387(18) -0.0048(15) 0.0060(14) 0.0028(15) C16 0.0386(16) 0.0453(18) 0.0391(18) -0.0100(14) 0.0033(14) -0.0002(14) C17 0.0402(16) 0.0384(17) 0.0445(18) -0.0109(14) 0.0085(14) -0.0010(14) C18 0.0373(16) 0.0402(17) 0.0466(18) -0.0054(15) 0.0105(14) 0.0012(14) C19 0.0422(18) 0.050(2) 0.064(2) -0.0061(17) 0.0051(16) -0.0025(15) C20 0.057(2) 0.047(2) 0.076(3) 0.0100(18) 0.0071(18) -0.0059(16) C21 0.063(2) 0.059(2) 0.062(2) 0.0104(18) 0.0030(18) 0.0033(18) C22 0.0466(18) 0.050(2) 0.0499(19) -0.0020(16) 0.0057(15) 0.0009(15) C23 0.0387(16) 0.0438(18) 0.0418(18) -0.0077(14) 0.0086(13) 0.0007(14) C24 0.0365(15) 0.0402(17) 0.0411(17) -0.0090(14) 0.0071(13) 0.0002(13) N5 0.0380(13) 0.0552(15) 0.0419(14) -0.0036(12) 0.0123(11) 0.0006(12) C25 0.0432(17) 0.0515(19) 0.0480(18) -0.0024(15) 0.0125(14) -0.0007(15) C26 0.057(2) 0.060(2) 0.067(2) -0.0003(17) 0.0088(17) 0.0159(17) C27 0.078(2) 0.051(2) 0.067(2) 0.0030(18) 0.0131(19) 0.0098(18) C28 0.091(3) 0.065(2) 0.094(3) -0.018(2) -0.003(2) -0.001(2) C29 0.0343(16) 0.070(2) 0.052(2) -0.0010(16) 0.0082(14) 0.0011(15) C30 0.0477(19) 0.070(2) 0.050(2) -0.0043(16) 0.0060(15) 0.0045(16) C31 0.051(2) 0.079(2) 0.062(2) -0.0017(19) 0.0027(16) 0.0054(18) C32 0.070(2) 0.123(3) 0.068(3) -0.014(2) -0.0105(19) 0.018(2) C33 0.0407(17) 0.0518(19) 0.0482(18) -0.0026(15) 0.0110(14) 0.0026(14) C34 0.0517(19) 0.054(2) 0.060(2) 0.0031(16) 0.0092(16) -0.0072(16) C35 0.065(2) 0.050(2) 0.066(2) 0.0014(17) 0.0036(18) -0.0020(17) C36 0.086(3) 0.072(3) 0.081(3) 0.002(2) -0.013(2) 0.007(2) C37 0.0498(19) 0.069(2) 0.0432(18) -0.0040(16) 0.0156(15) 0.0006(16) C38 0.061(2) 0.089(3) 0.052(2) -0.0066(19) 0.0040(17) 0.0032(19) C39 0.077(3) 0.097(3) 0.047(2) -0.0033(19) 0.0012(19) -0.011(2) C40 0.101(3) 0.121(4) 0.067(3) 0.003(2) -0.011(2) -0.008(3) Si1 0.0388(7) 0.0688(9) 0.0442(7) -0.0158(6) 0.0054(5) -0.0100(6) F1 0.0884(14) 0.1036(16) 0.0613(13) 0.0043(11) -0.0143(11) -0.0135(12) F2 0.0505(11) 0.1159(17) 0.0945(15) -0.0122(13) 0.0190(10) -0.0220(11) F3 0.0769(14) 0.0882(15) 0.0956(15) -0.0447(12) 0.0051(11) -0.0016(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 N1 C8 1.348(3) . ? N1 C1 1.376(3) . ? N2 C7 1.346(3) . ? N2 C6 1.376(3) . ? N3 C16 1.387(3) . ? N3 C15 1.398(4) . ? N3 H3A 0.892(10) . ? N4 C17 1.387(3) . ? N4 C18 1.396(3) . ? N4 H4A 0.899(10) . ? C1 C2 1.426(4) . ? C1 C6 1.426(4) . ? C2 C3 1.368(4) . ? C2 H2 0.9300 . ? C3 C4 1.410(5) . ? C3 H3 0.9300 . ? C4 C5 1.379(4) . ? C4 H4 0.9300 . ? C5 C6 1.427(4) . ? C5 H5 0.9300 . ? C7 C24 1.455(4) . ? C7 C8 1.469(4) . ? C8 C9 1.443(4) . ? C9 C16 1.405(4) . ? C9 C10 1.460(4) . ? C10 C11 1.415(4) . ? C10 C15 1.428(4) . ? C11 C12 1.385(4) . ? C11 H11 0.9300 . ? C12 C13 1.408(4) . ? C12 H12 0.9300 . ? C13 C14 1.388(4) . ? C13 H13 0.9300 . ? C14 C15 1.402(4) . ? C14 H14 0.9300 . ? C16 C17 1.427(4) . ? C17 C24 1.408(4) . ? C18 C19 1.400(4) . ? C18 C23 1.425(4) . ? C19 C20 1.391(4) . ? C19 H19 0.9300 . ? C20 C21 1.411(4) . ? C20 H20 0.9300 . ? C21 C22 1.392(4) . ? C21 H21 0.9300 . ? C22 C23 1.415(4) . ? C22 H22 0.9300 . ? C23 C24 1.456(4) . ? N5 C33 1.529(3) . ? N5 C37 1.534(3) . ? N5 C25 1.540(3) . ? N5 C29 1.542(3) . ? C25 C26 1.531(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.528(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.535(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.525(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.530(4) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.518(4) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.534(4) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.543(4) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.527(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C38 1.527(4) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.528(4) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.522(4) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? Si1 F2 1.6760(17) 3_666 ? Si1 F2 1.6761(17) . ? Si1 F3 1.6875(18) 3_666 ? Si1 F3 1.6875(18) . ? Si1 F1 1.7072(19) . ? Si1 F1 1.7072(19) 3_666 ? 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 C8 N1 C1 116.9(2) . . ? C7 N2 C6 116.7(2) . . ? C16 N3 C15 108.4(2) . . ? C16 N3 H3A 126(2) . . ? C15 N3 H3A 125(2) . . ? C17 N4 C18 108.4(2) . . ? C17 N4 H4A 126(2) . . ? C18 N4 H4A 125(2) . . ? N1 C1 C2 119.1(3) . . ? N1 C1 C6 121.6(3) . . ? C2 C1 C6 119.3(3) . . ? C3 C2 C1 120.9(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.8(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N2 C6 C1 121.9(2) . . ? N2 C6 C5 119.7(3) . . ? C1 C6 C5 118.4(3) . . ? N2 C7 C24 120.2(2) . . ? N2 C7 C8 121.6(2) . . ? C24 C7 C8 118.2(2) . . ? N1 C8 C9 120.0(2) . . ? N1 C8 C7 121.3(2) . . ? C9 C8 C7 118.7(2) . . ? C16 C9 C8 121.2(3) . . ? C16 C9 C10 106.6(2) . . ? C8 C9 C10 132.2(2) . . ? C11 C10 C15 118.8(3) . . ? C11 C10 C9 135.0(3) . . ? C15 C10 C9 106.1(2) . . ? C12 C11 C10 118.8(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C13 121.5(3) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 117.9(3) . . ? C13 C14 H14 121.1 . . ? C15 C14 H14 121.1 . . ? N3 C15 C14 129.3(3) . . ? N3 C15 C10 108.9(2) . . ? C14 C15 C10 121.8(3) . . ? N3 C16 C9 110.0(2) . . ? N3 C16 C17 129.5(3) . . ? C9 C16 C17 120.5(2) . . ? N4 C17 C24 110.2(2) . . ? N4 C17 C16 129.4(2) . . ? C24 C17 C16 120.3(2) . . ? N4 C18 C19 129.0(3) . . ? N4 C18 C23 108.5(2) . . ? C19 C18 C23 122.5(3) . . ? C20 C19 C18 117.5(3) . . ? C20 C19 H19 121.2 . . ? C18 C19 H19 121.2 . . ? C19 C20 C21 121.3(3) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C22 C21 C20 121.1(3) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 119.0(3) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C22 C23 C18 118.5(3) . . ? C22 C23 C24 134.6(3) . . ? C18 C23 C24 106.9(2) . . ? C17 C24 C7 121.0(3) . . ? C17 C24 C23 105.9(2) . . ? C7 C24 C23 133.0(2) . . ? C33 N5 C37 110.9(2) . . ? C33 N5 C25 106.46(19) . . ? C37 N5 C25 111.1(2) . . ? C33 N5 C29 111.2(2) . . ? C37 N5 C29 106.2(2) . . ? C25 N5 C29 111.1(2) . . ? C26 C25 N5 116.1(2) . . ? C26 C25 H25A 108.3 . . ? N5 C25 H25A 108.3 . . ? C26 C25 H25B 108.3 . . ? N5 C25 H25B 108.3 . . ? H25A C25 H25B 107.4 . . ? C27 C26 C25 111.5(2) . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26B 109.3 . . ? C25 C26 H26B 109.3 . . ? H26A C26 H26B 108.0 . . ? C26 C27 C28 113.0(3) . . ? C26 C27 H27A 109.0 . . ? C28 C27 H27A 109.0 . . ? C26 C27 H27B 109.0 . . ? C28 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 N5 116.5(2) . . ? C30 C29 H29A 108.2 . . ? N5 C29 H29A 108.2 . . ? C30 C29 H29B 108.2 . . ? N5 C29 H29B 108.2 . . ? H29A C29 H29B 107.3 . . ? C29 C30 C31 109.8(2) . . ? C29 C30 H30A 109.7 . . ? C31 C30 H30A 109.7 . . ? C29 C30 H30B 109.7 . . ? C31 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? C32 C31 C30 113.3(3) . . ? C32 C31 H31A 108.9 . . ? C30 C31 H31A 108.9 . . ? C32 C31 H31B 108.9 . . ? C30 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N5 C33 C34 116.3(2) . . ? N5 C33 H33A 108.2 . . ? C34 C33 H33A 108.2 . . ? N5 C33 H33B 108.2 . . ? C34 C33 H33B 108.2 . . ? H33A C33 H33B 107.4 . . ? C33 C34 C35 111.1(2) . . ? C33 C34 H34A 109.4 . . ? C35 C34 H34A 109.4 . . ? C33 C34 H34B 109.4 . . ? C35 C34 H34B 109.4 . . ? H34A C34 H34B 108.0 . . ? C36 C35 C34 114.2(3) . . ? C36 C35 H35A 108.7 . . ? C34 C35 H35A 108.7 . . ? C36 C35 H35B 108.7 . . ? C34 C35 H35B 108.7 . . ? H35A C35 H35B 107.6 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 N5 116.8(2) . . ? C38 C37 H37A 108.1 . . ? N5 C37 H37A 108.1 . . ? C38 C37 H37B 108.1 . . ? N5 C37 H37B 108.1 . . ? H37A C37 H37B 107.3 . . ? C37 C38 C39 110.2(3) . . ? C37 C38 H38A 109.6 . . ? C39 C38 H38A 109.6 . . ? C37 C38 H38B 109.6 . . ? C39 C38 H38B 109.6 . . ? H38A C38 H38B 108.1 . . ? C40 C39 C38 113.1(3) . . ? C40 C39 H39A 109.0 . . ? C38 C39 H39A 109.0 . . ? C40 C39 H39B 109.0 . . ? C38 C39 H39B 109.0 . . ? H39A C39 H39B 107.8 . . ? 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 . . ? F2 Si1 F2 180.0 3_666 . ? F2 Si1 F3 91.47(10) 3_666 3_666 ? F2 Si1 F3 88.53(10) . 3_666 ? F2 Si1 F3 88.53(10) 3_666 . ? F2 Si1 F3 91.47(10) . . ? F3 Si1 F3 180.00(12) 3_666 . ? F2 Si1 F1 89.96(10) 3_666 . ? F2 Si1 F1 90.04(10) . . ? F3 Si1 F1 89.28(10) 3_666 . ? F3 Si1 F1 90.72(10) . . ? F2 Si1 F1 90.04(10) 3_666 3_666 ? F2 Si1 F1 89.96(10) . 3_666 ? F3 Si1 F1 90.72(10) 3_666 3_666 ? F3 Si1 F1 89.28(10) . 3_666 ? F1 Si1 F1 180.00(19) . 3_666 ? 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 C8 N1 C1 C2 178.4(3) . . . . ? C8 N1 C1 C6 -0.9(4) . . . . ? N1 C1 C2 C3 -179.6(3) . . . . ? C6 C1 C2 C3 -0.3(4) . . . . ? C1 C2 C3 C4 -1.5(5) . . . . ? C2 C3 C4 C5 1.6(5) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? C7 N2 C6 C1 -0.4(4) . . . . ? C7 N2 C6 C5 -179.7(3) . . . . ? N1 C1 C6 N2 2.0(4) . . . . ? C2 C1 C6 N2 -177.4(3) . . . . ? N1 C1 C6 C5 -178.7(3) . . . . ? C2 C1 C6 C5 2.0(4) . . . . ? C4 C5 C6 N2 177.5(3) . . . . ? C4 C5 C6 C1 -1.9(4) . . . . ? C6 N2 C7 C24 -179.6(2) . . . . ? C6 N2 C7 C8 -2.0(4) . . . . ? C1 N1 C8 C9 179.2(2) . . . . ? C1 N1 C8 C7 -1.5(4) . . . . ? N2 C7 C8 N1 3.1(4) . . . . ? C24 C7 C8 N1 -179.2(2) . . . . ? N2 C7 C8 C9 -177.5(2) . . . . ? C24 C7 C8 C9 0.1(3) . . . . ? N1 C8 C9 C16 179.1(2) . . . . ? C7 C8 C9 C16 -0.3(4) . . . . ? N1 C8 C9 C10 -0.6(4) . . . . ? C7 C8 C9 C10 -179.9(3) . . . . ? C16 C9 C10 C11 177.3(3) . . . . ? C8 C9 C10 C11 -3.0(5) . . . . ? C16 C9 C10 C15 -1.2(3) . . . . ? C8 C9 C10 C15 178.5(3) . . . . ? C15 C10 C11 C12 -0.5(4) . . . . ? C9 C10 C11 C12 -178.8(3) . . . . ? C10 C11 C12 C13 -0.8(5) . . . . ? C11 C12 C13 C14 0.8(5) . . . . ? C12 C13 C14 C15 0.6(5) . . . . ? C16 N3 C15 C14 -179.9(3) . . . . ? C16 N3 C15 C10 0.0(3) . . . . ? C13 C14 C15 N3 178.0(3) . . . . ? C13 C14 C15 C10 -1.9(4) . . . . ? C11 C10 C15 N3 -178.1(2) . . . . ? C9 C10 C15 N3 0.7(3) . . . . ? C11 C10 C15 C14 1.9(4) . . . . ? C9 C10 C15 C14 -179.3(2) . . . . ? C15 N3 C16 C9 -0.8(3) . . . . ? C15 N3 C16 C17 179.0(3) . . . . ? C8 C9 C16 N3 -178.5(2) . . . . ? C10 C9 C16 N3 1.3(3) . . . . ? C8 C9 C16 C17 1.7(4) . . . . ? C10 C9 C16 C17 -178.6(2) . . . . ? C18 N4 C17 C24 -0.6(3) . . . . ? C18 N4 C17 C16 -179.4(3) . . . . ? N3 C16 C17 N4 -4.1(5) . . . . ? C9 C16 C17 N4 175.7(3) . . . . ? N3 C16 C17 C24 177.3(3) . . . . ? C9 C16 C17 C24 -2.9(4) . . . . ? C17 N4 C18 C19 178.7(3) . . . . ? C17 N4 C18 C23 -0.3(3) . . . . ? N4 C18 C19 C20 -179.7(3) . . . . ? C23 C18 C19 C20 -0.8(4) . . . . ? C18 C19 C20 C21 -0.2(4) . . . . ? C19 C20 C21 C22 0.6(5) . . . . ? C20 C21 C22 C23 0.1(4) . . . . ? C21 C22 C23 C18 -1.0(4) . . . . ? C21 C22 C23 C24 178.2(3) . . . . ? N4 C18 C23 C22 -179.5(2) . . . . ? C19 C18 C23 C22 1.4(4) . . . . ? N4 C18 C23 C24 1.1(3) . . . . ? C19 C18 C23 C24 -178.0(2) . . . . ? N4 C17 C24 C7 -176.1(2) . . . . ? C16 C17 C24 C7 2.7(4) . . . . ? N4 C17 C24 C23 1.3(3) . . . . ? C16 C17 C24 C23 -179.9(2) . . . . ? N2 C7 C24 C17 176.3(2) . . . . ? C8 C7 C24 C17 -1.3(4) . . . . ? N2 C7 C24 C23 -0.2(4) . . . . ? C8 C7 C24 C23 -177.9(3) . . . . ? C22 C23 C24 C17 179.3(3) . . . . ? C18 C23 C24 C17 -1.4(3) . . . . ? C22 C23 C24 C7 -3.8(5) . . . . ? C18 C23 C24 C7 175.5(3) . . . . ? C33 N5 C25 C26 -178.0(2) . . . . ? C37 N5 C25 C26 61.1(3) . . . . ? C29 N5 C25 C26 -56.9(3) . . . . ? N5 C25 C26 C27 -166.0(2) . . . . ? C25 C26 C27 C28 72.3(3) . . . . ? C33 N5 C29 C30 54.2(3) . . . . ? C37 N5 C29 C30 174.9(3) . . . . ? C25 N5 C29 C30 -64.2(3) . . . . ? N5 C29 C30 C31 170.8(3) . . . . ? C29 C30 C31 C32 166.1(3) . . . . ? C37 N5 C33 C34 -60.9(3) . . . . ? C25 N5 C33 C34 178.1(2) . . . . ? C29 N5 C33 C34 57.0(3) . . . . ? N5 C33 C34 C35 164.5(2) . . . . ? C33 C34 C35 C36 -73.7(3) . . . . ? C33 N5 C37 C38 -51.6(3) . . . . ? C25 N5 C37 C38 66.6(3) . . . . ? C29 N5 C37 C38 -172.5(3) . . . . ? N5 C37 C38 C39 -168.5(3) . . . . ? C37 C38 C39 C40 -164.7(3) . . . . ? 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 N3 H3A F3 0.892(10) 2.042(15) 2.888(3) 158(3) 3_666 N4 H4A F1 0.899(10) 1.898(14) 2.770(3) 163(3) . N3 H3A F2 0.892(10) 2.41(2) 3.120(3) 136(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.227 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.038