# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Wim Dehaen' 'Rong Gu.' 'Koen Robeyns' 'Suzanne Toppet' 'Luc Van Meervelt' _publ_contact_author_name 'Wim Dehaen' _publ_contact_author_email WIM.DEHAEN@CHEM.KULEUVEN.BE _publ_section_title ; Facile synthesis of novel indolo[3,2-b]carbazole derivatives and a chromogenic-sensing 5,12-dihydroindolo[3,2-b]carbazole ; # Attachment 'X-ray_of_compound_4a' data_wim55 _database_code_depnum_ccdc_archive 'CCDC 686527' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H53 N2 3(C2 H6 O S)' _chemical_formula_sum 'C45 H71 N2 O3 S3' _chemical_formula_weight 784.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .3331 .5567 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0489(3) _cell_length_b 9.1351(3) _cell_length_c 14.2792(5) _cell_angle_alpha 96.789(2) _cell_angle_beta 103.990(2) _cell_angle_gamma 99.109(2) _cell_volume 1115.71(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 71.67 _exptl_crystal_description block _exptl_crystal_colour transparent _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 427 _exptl_absorpt_coefficient_mu 1.789 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.622 _exptl_absorpt_correction_T_max 0.836 _exptl_absorpt_process_details 'Bruker SADABS (SADABS, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed Goebel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method 'omega and phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number na _diffrn_standards_interval_count na _diffrn_standards_interval_time na _diffrn_standards_decay_% na _diffrn_reflns_number 21872 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 71.67 _reflns_number_total 4308 _reflns_number_gt 3888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (SMART, 1997)' _computing_cell_refinement 'Bruker SAINT (SAINT, 1997)' _computing_data_reduction 'Bruker SAINT (SAINT, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0082P)^2^+2.8056P] 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 4308 _refine_ls_number_parameters 329 _refine_ls_number_restraints 228 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.1783 _refine_ls_wR_factor_gt 0.1757 _refine_ls_goodness_of_fit_ref 1.250 _refine_ls_restrained_S_all 1.222 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3419(3) 0.6622(3) 0.10218(19) 0.0217(6) Uani 1 1 d U . . H1 H 0.2604 0.7029 0.0818 0.026 Uiso 1 1 calc R . . C2 C 0.4200(4) 0.6679(4) 0.1998(2) 0.0200(6) Uani 1 1 d U . . C3 C 0.3911(4) 0.7313(4) 0.2869(2) 0.0199(6) Uani 1 1 d U . . C4 C 0.4956(4) 0.7163(4) 0.3734(2) 0.0201(6) Uani 1 1 d U . . H4 H 0.4794 0.7577 0.4335 0.024 Uiso 1 1 calc R . . C5 C 0.6231(4) 0.6444(4) 0.3779(2) 0.0215(7) Uani 1 1 d U . . C6 C 0.6460(4) 0.5809(4) 0.2909(2) 0.0215(7) Uani 1 1 d U . . H6 H 0.7301 0.5302 0.2918 0.026 Uiso 1 1 calc R . . C7 C 0.5454(4) 0.5913(4) 0.2018(2) 0.0205(7) Uani 1 1 d U . . C8 C 0.5393(4) 0.5342(4) 0.1016(2) 0.0213(7) Uani 1 1 d U A . C9 C 0.4115(4) 0.5826(4) 0.0416(2) 0.0213(7) Uani 1 1 d U . . C10 C 0.6307(4) 0.4499(4) 0.0596(2) 0.0224(7) Uani 1 1 d U . . C11 C 0.2519(4) 0.8071(4) 0.2881(2) 0.0227(7) Uani 1 1 d U . . C12 C 0.1006(4) 0.6905(4) 0.2427(3) 0.0254(7) Uani 1 1 d U . . H12A H 0.0978 0.6079 0.2807 0.038 Uiso 1 1 calc R . . H12B H 0.0964 0.6509 0.1750 0.038 Uiso 1 1 calc R . . H12C H 0.0112 0.7384 0.2434 0.038 Uiso 1 1 calc R . . C13 C 0.2568(4) 0.9412(4) 0.2320(3) 0.0269(7) Uani 1 1 d U . . H13A H 0.1666 0.9876 0.2331 0.040 Uiso 1 1 calc R . . H13B H 0.2548 0.9059 0.1640 0.040 Uiso 1 1 calc R . . H13C H 0.3522 1.0155 0.2630 0.040 Uiso 1 1 calc R . . C14 C 0.2502(4) 0.8694(4) 0.3924(3) 0.0273(7) Uani 1 1 d U . . H14A H 0.2402 0.7867 0.4297 0.041 Uiso 1 1 calc R . . H14B H 0.1621 0.9204 0.3897 0.041 Uiso 1 1 calc R . . H14C H 0.3471 0.9411 0.4243 0.041 Uiso 1 1 calc R . . C15 C 0.7404(4) 0.6430(4) 0.4756(2) 0.0249(7) Uani 1 1 d U . . C16 C 0.6815(4) 0.6834(4) 0.5652(3) 0.0306(8) Uani 1 1 d U . . H16A H 0.5856 0.6128 0.5608 0.046 Uiso 1 1 calc R . . H16B H 0.6609 0.7858 0.5678 0.046 Uiso 1 1 calc R . . H16C H 0.7603 0.6777 0.6246 0.046 Uiso 1 1 calc R . . C17 C 0.8891(4) 0.7577(5) 0.4826(3) 0.0358(9) Uani 1 1 d U . . H17A H 0.8651 0.8587 0.4836 0.054 Uiso 1 1 calc R . . H17B H 0.9287 0.7321 0.4259 0.054 Uiso 1 1 calc R . . H17C H 0.9678 0.7552 0.5428 0.054 Uiso 1 1 calc R . . C18 C 0.7829(4) 0.4870(4) 0.4793(3) 0.0310(8) Uani 1 1 d U . . H18A H 0.8603 0.4892 0.5410 0.047 Uiso 1 1 calc R . . H18B H 0.8259 0.4598 0.4244 0.047 Uiso 1 1 calc R . . H18C H 0.6897 0.4126 0.4749 0.047 Uiso 1 1 calc R . . C19 C 0.7530(7) 0.3848(7) 0.1221(4) 0.0194(13) Uani 0.50 1 d PU A 1 H19A H 0.8117 0.4619 0.1793 0.023 Uiso 0.50 1 calc PR A 1 H19B H 0.8266 0.3603 0.0842 0.023 Uiso 0.50 1 calc PR A 1 C20 C 0.6895(8) 0.2425(8) 0.1590(5) 0.0262(14) Uani 0.50 1 d PU A 1 H20A H 0.6276 0.1666 0.1020 0.031 Uiso 0.50 1 calc PR A 1 H20B H 0.6193 0.2677 0.1993 0.031 Uiso 0.50 1 calc PR A 1 C21 C 0.819(3) 0.173(2) 0.2206(17) 0.051(5) Uani 0.50 1 d PU A 1 H21A H 0.8857 0.1428 0.1793 0.061 Uiso 0.50 1 calc PR A 1 H21B H 0.8839 0.2504 0.2757 0.061 Uiso 0.50 1 calc PR A 1 C22 C 0.7546(10) 0.0353(10) 0.2616(7) 0.0354(17) Uani 0.50 1 d PU A 1 H22A H 0.6719 -0.0337 0.2096 0.043 Uiso 0.50 1 calc PR A 1 H22B H 0.8385 -0.0196 0.2853 0.043 Uiso 0.50 1 calc PR A 1 C23 C 0.6900(9) 0.0880(9) 0.3445(6) 0.0245(15) Uani 0.50 1 d PU A 1 H23A H 0.7749 0.1455 0.3992 0.037 Uiso 0.50 1 calc PR A 1 H23B H 0.6376 0.0009 0.3659 0.037 Uiso 0.50 1 calc PR A 1 H23C H 0.6156 0.1520 0.3224 0.037 Uiso 0.50 1 calc PR A 1 S51 S 0.1012(7) 0.3014(8) 0.0100(4) 0.0242(9) Uani 0.50 1 d PDU B 3 O52 O -0.0605(11) 0.2082(17) -0.0136(8) 0.028(2) Uani 0.50 1 d PDU B 3 C53 C 0.1846(18) 0.306(3) 0.1373(8) 0.037(4) Uani 0.50 1 d PDU B 3 H53A H 0.1297 0.3623 0.1755 0.055 Uiso 0.50 1 calc PR B 3 H53B H 0.2944 0.3540 0.1547 0.055 Uiso 0.50 1 calc PR B 3 H53C H 0.1755 0.2026 0.1515 0.055 Uiso 0.50 1 calc PR B 3 C54 C 0.2110(14) 0.1790(15) -0.0339(10) 0.029(3) Uani 0.50 1 d PDU B 3 H54A H 0.2032 0.0886 -0.0032 0.043 Uiso 0.50 1 calc PR B 3 H54B H 0.3200 0.2298 -0.0177 0.043 Uiso 0.50 1 calc PR B 3 H54C H 0.1709 0.1507 -0.1050 0.043 Uiso 0.50 1 calc PR B 3 S61 S 0.8069(5) 0.1253(4) 0.2292(4) 0.0373(9) Uani 0.50 1 d PU C 2 O62 O 0.8608(6) 0.2900(6) 0.2582(4) 0.0374(12) Uani 0.50 1 d PU C 2 C63 C 0.6320(10) 0.0928(10) 0.1330(6) 0.0412(19) Uani 0.50 1 d PU C 2 H63A H 0.5606 0.1536 0.1519 0.062 Uiso 0.50 1 calc PR C 2 H63B H 0.5833 -0.0138 0.1209 0.062 Uiso 0.50 1 calc PR C 2 H63C H 0.6559 0.1207 0.0734 0.062 Uiso 0.50 1 calc PR C 2 C64 C 0.7229(17) 0.0538(17) 0.3182(11) 0.066(4) Uani 0.50 1 d PU C 2 H64A H 0.8051 0.0500 0.3763 0.098 Uiso 0.50 1 calc PR C 2 H64B H 0.6620 -0.0475 0.2914 0.098 Uiso 0.50 1 calc PR C 2 H64C H 0.6549 0.1195 0.3362 0.098 Uiso 0.50 1 calc PR C 2 S71 S 0.0716(7) 0.3029(8) 0.0289(4) 0.0270(10) Uani 0.50 1 d PDU D 4 O72 O -0.0900(10) 0.2129(16) 0.0069(7) 0.026(2) Uani 0.50 1 d PDU D 4 C73 C 0.1589(17) 0.304(2) 0.1555(8) 0.024(3) Uani 0.50 1 d PDU D 4 H73A H 0.1030 0.3571 0.1952 0.036 Uiso 0.50 1 calc PR D 4 H73B H 0.2676 0.3563 0.1725 0.036 Uiso 0.50 1 calc PR D 4 H73C H 0.1540 0.2009 0.1682 0.036 Uiso 0.50 1 calc PR D 4 C74 C 0.1822(15) 0.1825(15) -0.0191(10) 0.040(3) Uani 0.50 1 d PDU D 4 H74A H 0.1633 0.0846 0.0019 0.060 Uiso 0.50 1 calc PR D 4 H74B H 0.2929 0.2276 0.0050 0.060 Uiso 0.50 1 calc PR D 4 H74C H 0.1513 0.1692 -0.0908 0.060 Uiso 0.50 1 calc PR D 4 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 0.0232(13) 0.0272(15) 0.0196(13) 0.0056(11) 0.0073(11) 0.0152(11) C2 0.0221(15) 0.0198(15) 0.0203(15) 0.0056(12) 0.0063(12) 0.0073(12) C3 0.0235(16) 0.0169(15) 0.0218(16) 0.0053(12) 0.0080(12) 0.0066(12) C4 0.0243(16) 0.0191(15) 0.0197(15) 0.0042(12) 0.0096(12) 0.0060(12) C5 0.0226(16) 0.0202(16) 0.0226(16) 0.0066(13) 0.0061(13) 0.0043(13) C6 0.0207(15) 0.0223(16) 0.0249(16) 0.0071(13) 0.0077(13) 0.0089(13) C7 0.0212(15) 0.0212(16) 0.0219(16) 0.0060(13) 0.0075(12) 0.0083(12) C8 0.0236(15) 0.0240(16) 0.0205(15) 0.0065(13) 0.0090(13) 0.0101(13) C9 0.0224(15) 0.0229(16) 0.0230(16) 0.0057(13) 0.0095(13) 0.0102(13) C10 0.0248(16) 0.0250(17) 0.0209(16) 0.0052(13) 0.0081(13) 0.0110(13) C11 0.0285(17) 0.0210(16) 0.0222(16) 0.0064(13) 0.0086(13) 0.0098(13) C12 0.0271(17) 0.0275(17) 0.0283(17) 0.0070(14) 0.0142(14) 0.0123(14) C13 0.0322(18) 0.0243(17) 0.0304(18) 0.0080(14) 0.0123(15) 0.0152(14) C14 0.0337(18) 0.0266(18) 0.0281(18) 0.0073(14) 0.0135(15) 0.0142(15) C15 0.0249(16) 0.0283(18) 0.0219(16) 0.0065(13) 0.0047(13) 0.0072(14) C16 0.0315(18) 0.037(2) 0.0223(17) 0.0074(15) 0.0032(14) 0.0080(16) C17 0.0272(18) 0.043(2) 0.0318(19) 0.0079(17) 0.0032(15) -0.0023(16) C18 0.0316(18) 0.037(2) 0.0262(18) 0.0118(15) 0.0049(14) 0.0125(16) C19 0.018(3) 0.027(3) 0.017(3) -0.002(2) 0.011(2) 0.008(2) C20 0.028(3) 0.025(3) 0.027(3) 0.007(3) 0.005(3) 0.010(3) C21 0.047(7) 0.061(10) 0.045(6) 0.010(7) 0.014(5) 0.010(7) C22 0.042(4) 0.028(4) 0.039(4) 0.009(3) 0.017(3) 0.004(3) C23 0.027(3) 0.022(3) 0.025(4) 0.003(3) 0.007(3) 0.004(3) S51 0.024(2) 0.0273(12) 0.024(2) 0.0094(13) 0.0063(12) 0.0068(13) O52 0.023(4) 0.039(4) 0.029(5) 0.009(3) 0.013(3) 0.013(3) C53 0.041(6) 0.031(5) 0.040(6) 0.013(6) 0.012(5) 0.004(5) C54 0.029(3) 0.029(3) 0.029(3) 0.0043(11) 0.0083(12) 0.0060(11) S61 0.0315(13) 0.0337(18) 0.0430(17) 0.0003(15) 0.0065(11) 0.0053(13) O62 0.041(3) 0.029(3) 0.043(3) -0.001(2) 0.019(2) 0.004(2) C63 0.040(4) 0.045(4) 0.038(4) 0.007(3) 0.006(3) 0.011(3) C64 0.065(4) 0.065(4) 0.066(4) 0.0109(12) 0.0172(15) 0.0122(13) S71 0.029(2) 0.0266(12) 0.029(2) 0.0142(15) 0.0095(12) 0.0087(14) O72 0.022(4) 0.036(3) 0.022(4) 0.005(3) 0.005(3) 0.011(3) C73 0.031(5) 0.027(5) 0.016(4) 0.005(4) 0.004(4) 0.011(4) C74 0.040(6) 0.045(6) 0.038(6) 0.012(4) 0.011(4) 0.009(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 N1 C9 1.390(4) . ? N1 C2 1.392(4) . ? N1 H1 0.8800 . ? C2 C3 1.409(5) . ? C2 C7 1.420(4) . ? C3 C4 1.398(4) . ? C3 C11 1.533(4) . ? C4 C5 1.407(5) . ? C4 H4 0.9500 . ? C5 C6 1.383(5) . ? C5 C15 1.538(4) . ? C6 C7 1.398(4) . ? C6 H6 0.9500 . ? C7 C8 1.449(5) . ? C8 C10 1.404(5) . ? C8 C9 1.427(4) . ? C9 C10 1.385(5) 2_665 ? C10 C9 1.385(5) 2_665 ? C10 C19 1.494(7) . ? C11 C14 1.534(5) . ? C11 C12 1.541(5) . ? C11 C13 1.543(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.530(5) . ? C15 C18 1.537(5) . ? C15 C17 1.543(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.539(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.55(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.539(17) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.504(12) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? S51 O52 1.509(9) . ? S51 C54 1.766(11) . ? S51 C53 1.784(11) . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? S61 O62 1.481(6) . ? S61 C64 1.767(16) . ? S61 C63 1.785(9) . ? C63 H63A 0.9800 . ? C63 H63B 0.9800 . ? C63 H63C 0.9800 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? S71 O72 1.499(9) . ? S71 C74 1.784(11) . ? S71 C73 1.787(10) . ? C73 H73A 0.9800 . ? C73 H73B 0.9800 . ? C73 H73C 0.9800 . ? C74 H74A 0.9800 . ? C74 H74B 0.9800 . ? C74 H74C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C2 109.9(3) . . ? C9 N1 H1 125.0 . . ? C2 N1 H1 125.0 . . ? N1 C2 C3 131.1(3) . . ? N1 C2 C7 107.8(3) . . ? C3 C2 C7 121.2(3) . . ? C4 C3 C2 115.5(3) . . ? C4 C3 C11 121.6(3) . . ? C2 C3 C11 122.9(3) . . ? C3 C4 C5 124.7(3) . . ? C3 C4 H4 117.7 . . ? C5 C4 H4 117.7 . . ? C6 C5 C4 118.2(3) . . ? C6 C5 C15 120.0(3) . . ? C4 C5 C15 121.7(3) . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C2 120.4(3) . . ? C6 C7 C8 131.9(3) . . ? C2 C7 C8 107.7(3) . . ? C10 C8 C9 120.8(3) . . ? C10 C8 C7 133.0(3) . . ? C9 C8 C7 106.2(3) . . ? C10 C9 N1 128.4(3) 2_665 . ? C10 C9 C8 123.2(3) 2_665 . ? N1 C9 C8 108.4(3) . . ? C9 C10 C8 116.0(3) 2_665 . ? C9 C10 C19 122.8(4) 2_665 . ? C8 C10 C19 120.7(3) . . ? C3 C11 C14 112.1(3) . . ? C3 C11 C12 109.2(3) . . ? C14 C11 C12 107.5(3) . . ? C3 C11 C13 110.7(3) . . ? C14 C11 C13 106.6(3) . . ? C12 C11 C13 110.6(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C18 107.4(3) . . ? C16 C15 C5 113.7(3) . . ? C18 C15 C5 110.7(3) . . ? C16 C15 C17 108.7(3) . . ? C18 C15 C17 108.4(3) . . ? C5 C15 C17 107.9(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 C20 114.1(5) . . ? C10 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? C10 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 113.4(9) . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 113.3(14) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C23 C22 C21 108.8(11) . . ? C23 C22 H22A 109.9 . . ? C21 C22 H22A 109.9 . . ? C23 C22 H22B 109.9 . . ? C21 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? O52 S51 C54 104.5(7) . . ? O52 S51 C53 106.2(7) . . ? C54 S51 C53 97.0(8) . . ? O62 S61 C64 109.3(6) . . ? O62 S61 C63 107.8(4) . . ? C64 S61 C63 96.9(6) . . ? S61 C63 H63A 109.5 . . ? S61 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? S61 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? S61 C64 H64A 109.5 . . ? S61 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? S61 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? O72 S71 C74 106.1(7) . . ? O72 S71 C73 106.3(7) . . ? C74 S71 C73 97.2(7) . . ? _diffrn_measured_fraction_theta_max .987 _diffrn_reflns_theta_full 71.67 _diffrn_measured_fraction_theta_full .987 _refine_diff_density_max .334 _refine_diff_density_min -.308 _refine_diff_density_rms .065 # Attachment 'x-ray_of_compound_5a' data_wim79 _database_code_depnum_ccdc_archive 'CCDC 686528' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H50 N2' _chemical_formula_sum 'C46 H50 N2' _chemical_formula_weight 630.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7658(9) _cell_length_b 12.2250(15) _cell_length_c 13.2296(15) _cell_angle_alpha 79.379(7) _cell_angle_beta 81.877(9) _cell_angle_gamma 88.968(9) _cell_volume 907.3(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 975 _cell_measurement_theta_min 3.428 _cell_measurement_theta_max 70.104 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.498 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.782 _exptl_absorpt_correction_T_max 0.951 _exptl_absorpt_process_details 'Bruker SADABS (SADABS, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed Goebel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method 'omega and phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 11666 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 71.30 _reflns_number_total 3444 _reflns_number_gt 2507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (SMART, 1997)' _computing_cell_refinement 'Bruker SAINT (SAINT, 1997)' _computing_data_reduction 'Bruker SAINT (SAINT, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1998)' _computing_publication_material 'PLATON (Spek, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.2874P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3444 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1523 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4632(3) 0.27923(13) 0.07212(13) 0.0193(4) Uani 1 1 d . . . C2 C 0.4696(4) 0.38613(16) 0.03284(15) 0.0191(4) Uani 1 1 d . . . C3 C 0.5911(3) 0.45240(16) 0.09147(15) 0.0195(4) Uani 1 1 d . . . C4 C 0.6622(4) 0.36931(16) 0.17627(15) 0.0195(4) Uani 1 1 d . . . C5 C 0.7862(4) 0.37632(16) 0.25747(15) 0.0205(4) Uani 1 1 d . . . H5 H 0.8468(17) 0.4456(19) 0.2649(3) 0.025 Uiso 1 1 calc R . . C6 C 0.8201(4) 0.27861(17) 0.32848(15) 0.0208(4) Uani 1 1 d . . . C7 C 0.7324(4) 0.17827(17) 0.31347(15) 0.0209(4) Uani 1 1 d . . . H7 H 0.7574(7) 0.1054(17) 0.3684(13) 0.025 Uiso 1 1 calc R . . C8 C 0.6123(3) 0.16708(16) 0.22985(15) 0.0194(4) Uani 1 1 d . . . C9 C 0.5795(4) 0.26644(16) 0.16212(15) 0.0192(4) Uani 1 1 d . . . C10 C 0.6236(4) 0.56407(16) 0.06124(15) 0.0198(4) Uani 1 1 d . . . C11 C 0.7493(4) 0.63302(15) 0.11854(15) 0.0188(4) Uani 1 1 d . . . C12 C 0.9577(4) 0.68771(17) 0.07166(16) 0.0233(4) Uani 1 1 d . . . H12 H 1.0140(16) 0.68756(17) -0.001(2) 0.028 Uiso 1 1 calc R . . C13 C 1.0856(4) 0.74266(18) 0.12938(17) 0.0266(5) Uani 1 1 d . . . H13 H 1.227(5) 0.7783(12) 0.0981(10) 0.032 Uiso 1 1 calc R . . C14 C 1.0049(4) 0.74500(17) 0.23279(17) 0.0263(5) Uani 1 1 d . . . H14 H 1.097(3) 0.7826(11) 0.2733(12) 0.032 Uiso 1 1 calc R . . C15 C 0.7935(4) 0.69376(17) 0.27833(16) 0.0243(5) Uani 1 1 d . . . H15 H 0.7344(18) 0.69684(19) 0.350(2) 0.029 Uiso 1 1 calc R . . C16 C 0.6655(4) 0.63798(17) 0.22171(16) 0.0220(4) Uani 1 1 d . . . H16 H 0.523(4) 0.6037(11) 0.2529(10) 0.026 Uiso 1 1 calc R . . C17 C 0.9444(4) 0.28828(17) 0.42219(15) 0.0219(4) Uani 1 1 d . . . C18 C 1.1688(4) 0.3585(2) 0.38652(18) 0.0350(6) Uani 1 1 d . . . H18A H 1.250(2) 0.3643(13) 0.4500(11) 0.052 Uiso 1 1 calc R . . H18B H 1.1272(9) 0.4370(14) 0.3504(14) 0.052 Uiso 1 1 calc R . . H18C H 1.280(2) 0.3213(10) 0.3351(14) 0.052 Uiso 1 1 calc R . . C19 C 0.7765(5) 0.3458(2) 0.49648(18) 0.0370(6) Uani 1 1 d . . . H19A H 0.631(3) 0.2968(12) 0.5242(13) 0.056 Uiso 1 1 calc R . . H19B H 0.728(3) 0.4210(16) 0.4575(8) 0.056 Uiso 1 1 calc R . . H19C H 0.8589(19) 0.3579(16) 0.5572(14) 0.056 Uiso 1 1 calc R . . C20 C 1.0101(5) 0.1755(2) 0.48102(19) 0.0356(6) Uani 1 1 d . . . H20A H 1.098(4) 0.1866(3) 0.5396(15) 0.053 Uiso 1 1 calc R . . H20B H 1.113(4) 0.1345(11) 0.4318(9) 0.053 Uiso 1 1 calc R . . H20C H 0.863(3) 0.1301(11) 0.5109(15) 0.053 Uiso 1 1 calc R . . C21 C 0.5279(4) 0.05386(16) 0.21438(16) 0.0216(4) Uani 1 1 d . . . C22 C 0.2654(4) 0.05646(18) 0.20553(19) 0.0295(5) Uani 1 1 d . . . H22A H 0.2346(8) 0.1168(14) 0.1474(13) 0.044 Uiso 1 1 calc R . . H22B H 0.1751(16) 0.0707(15) 0.2716(12) 0.044 Uiso 1 1 calc R . . H22C H 0.2162(11) -0.0164(13) 0.1918(14) 0.044 Uiso 1 1 calc R . . C23 C 0.6653(4) 0.02592(18) 0.11375(17) 0.0282(5) Uani 1 1 d . . . H23A H 0.623(3) -0.0487(14) 0.1064(8) 0.042 Uiso 1 1 calc R . . H23B H 0.833(3) 0.0292(15) 0.1169(6) 0.042 Uiso 1 1 calc R . . H23C H 0.627(3) 0.0796(13) 0.0544(10) 0.042 Uiso 1 1 calc R . . C24 C 0.5682(4) -0.03899(17) 0.30500(18) 0.0296(5) Uani 1 1 d . . . H24A H 0.479(3) -0.0209(9) 0.3735(11) 0.044 Uiso 1 1 calc R . . H24B H 0.746(3) -0.0450(11) 0.3103(10) 0.044 Uiso 1 1 calc R . . H24C H 0.507(3) -0.1139(13) 0.2924(8) 0.044 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 0.0179(8) 0.0214(8) 0.0186(8) -0.0008(6) -0.0060(6) -0.0017(7) C2 0.0172(10) 0.0216(9) 0.0188(9) -0.0029(7) -0.0041(7) -0.0011(8) C3 0.0169(10) 0.0218(10) 0.0201(9) -0.0025(7) -0.0054(7) -0.0005(8) C4 0.0171(10) 0.0226(9) 0.0181(9) -0.0014(7) -0.0034(7) -0.0018(7) C5 0.0194(10) 0.0209(10) 0.0219(10) -0.0034(8) -0.0060(8) -0.0015(8) C6 0.0162(10) 0.0261(10) 0.0198(10) -0.0022(8) -0.0043(7) -0.0006(8) C7 0.0173(10) 0.0253(10) 0.0197(9) -0.0023(8) -0.0034(8) 0.0013(8) C8 0.0149(9) 0.0220(10) 0.0204(9) -0.0017(7) -0.0027(7) -0.0002(8) C9 0.0172(10) 0.0220(9) 0.0188(9) -0.0031(7) -0.0052(7) -0.0008(8) C10 0.0170(10) 0.0220(9) 0.0210(10) -0.0037(8) -0.0050(7) -0.0010(8) C11 0.0190(10) 0.0171(9) 0.0208(9) -0.0014(7) -0.0069(8) 0.0009(7) C12 0.0235(11) 0.0263(10) 0.0204(10) -0.0030(8) -0.0058(8) -0.0025(8) C13 0.0228(11) 0.0296(11) 0.0276(11) -0.0034(9) -0.0051(9) -0.0079(9) C14 0.0298(12) 0.0241(10) 0.0278(11) -0.0064(8) -0.0114(9) -0.0033(9) C15 0.0294(12) 0.0234(10) 0.0211(10) -0.0054(8) -0.0058(8) 0.0015(9) C16 0.0195(10) 0.0227(10) 0.0240(10) -0.0028(8) -0.0057(8) -0.0024(8) C17 0.0204(10) 0.0267(10) 0.0195(10) -0.0033(8) -0.0078(8) 0.0010(8) C18 0.0272(12) 0.0484(14) 0.0304(12) -0.0006(10) -0.0154(10) -0.0100(11) C19 0.0333(13) 0.0580(16) 0.0250(11) -0.0160(11) -0.0123(10) 0.0111(12) C20 0.0471(15) 0.0337(12) 0.0302(12) -0.0031(10) -0.0239(11) 0.0037(11) C21 0.0201(10) 0.0212(10) 0.0234(10) -0.0013(8) -0.0063(8) -0.0015(8) C22 0.0208(11) 0.0247(10) 0.0433(13) -0.0033(9) -0.0090(9) -0.0040(9) C23 0.0282(12) 0.0275(11) 0.0314(11) -0.0093(9) -0.0072(9) -0.0008(9) C24 0.0338(13) 0.0219(10) 0.0336(12) -0.0002(9) -0.0121(10) -0.0023(9) _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 C2 1.314(3) . ? N1 C9 1.430(2) . ? C2 C10 1.451(3) 2_665 ? C2 C3 1.468(3) . ? C3 C10 1.358(3) . ? C3 C4 1.467(3) . ? C4 C5 1.388(3) . ? C4 C9 1.406(3) . ? C5 C6 1.406(3) . ? C5 H5 0.9488 . ? C6 C7 1.393(3) . ? C6 C17 1.540(3) . ? C7 C8 1.413(3) . ? C7 H7 1.0623 . ? C8 C9 1.397(3) . ? C8 C21 1.533(3) . ? C10 C2 1.451(3) 2_665 ? C10 C11 1.491(3) . ? C11 C12 1.393(3) . ? C11 C16 1.394(3) . ? C12 C13 1.394(3) . ? C12 H12 0.9742 . ? C13 C14 1.387(3) . ? C13 H13 0.9366 . ? C14 C15 1.386(3) . ? C14 H14 0.9782 . ? C15 C16 1.391(3) . ? C15 H15 0.9737 . ? C16 H16 0.9366 . ? C17 C20 1.523(3) . ? C17 C18 1.533(3) . ? C17 C19 1.536(3) . ? C18 H18A 1.0309 . ? C18 H18B 1.0309 . ? C18 H18C 1.0309 . ? C19 H19A 1.0229 . ? C19 H19B 1.0229 . ? C19 H19C 1.0229 . ? C20 H20A 1.0145 . ? C20 H20B 1.0145 . ? C20 H20C 1.0145 . ? C21 C24 1.532(3) . ? C21 C22 1.534(3) . ? C21 C23 1.541(3) . ? C22 H22A 0.9953 . ? C22 H22B 0.9953 . ? C22 H22C 0.9953 . ? C23 H23A 0.9746 . ? C23 H23B 0.9746 . ? C23 H23C 0.9746 . ? C24 H24A 1.0365 . ? C24 H24B 1.0365 . ? C24 H24C 1.0365 . ? 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 C2 N1 C9 106.19(16) . . ? N1 C2 C10 124.70(18) . 2_665 ? N1 C2 C3 113.22(17) . . ? C10 C2 C3 122.03(18) 2_665 . ? C10 C3 C4 134.14(18) . . ? C10 C3 C2 122.23(17) . . ? C4 C3 C2 103.59(16) . . ? C5 C4 C9 121.16(18) . . ? C5 C4 C3 133.08(18) . . ? C9 C4 C3 105.75(17) . . ? C4 C5 C6 118.62(18) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 118.84(18) . . ? C7 C6 C17 122.85(18) . . ? C5 C6 C17 118.26(18) . . ? C6 C7 C8 124.25(18) . . ? C6 C7 H7 117.9 . . ? C8 C7 H7 117.9 . . ? C9 C8 C7 114.96(18) . . ? C9 C8 C21 122.84(18) . . ? C7 C8 C21 122.19(17) . . ? C8 C9 C4 122.12(18) . . ? C8 C9 N1 126.65(18) . . ? C4 C9 N1 111.23(17) . . ? C3 C10 C2 115.74(17) . 2_665 ? C3 C10 C11 123.29(17) . . ? C2 C10 C11 120.96(17) 2_665 . ? C12 C11 C16 119.48(18) . . ? C12 C11 C10 120.47(18) . . ? C16 C11 C10 119.95(18) . . ? C11 C12 C13 119.87(19) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.56(19) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.1(2) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C20 C17 C18 108.13(19) . . ? C20 C17 C19 108.59(19) . . ? C18 C17 C19 109.17(19) . . ? C20 C17 C6 112.64(17) . . ? C18 C17 C6 110.37(17) . . ? C19 C17 C6 107.89(17) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C24 C21 C8 111.60(17) . . ? C24 C21 C22 107.99(18) . . ? C8 C21 C22 110.78(17) . . ? C24 C21 C23 108.48(18) . . ? C8 C21 C23 108.87(17) . . ? C22 C21 C23 109.07(18) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 67.70 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.259 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.057