# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_compound1 _database_code_depnum_ccdc_archive 'CCDC 879859' #TrackingRef 'compound1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N' _chemical_formula_weight 287.39 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 13.283(3) _cell_length_b 8.3330(14) _cell_length_c 15.160(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.272(2) _cell_angle_gamma 90.00 _cell_volume 1645.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123.1500 _cell_measurement_reflns_used 4295 _cell_measurement_theta_min 3.0758 _cell_measurement_theta_max 27.4899 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type None _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10602 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2878 _reflns_number_gt 2441 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0532P)^2^+0.4341P] 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 2878 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.14619(9) 0.56856(14) 0.51864(7) 0.0243(3) Uani 1 1 d . . . C1 C 0.11711(10) 0.51306(16) 0.59257(9) 0.0207(3) Uani 1 1 d . . . H1 H 0.0480 0.4788 0.5876 0.025 Uiso 1 1 calc R . . C2 C 0.18200(10) 0.50253(15) 0.67639(9) 0.0187(3) Uani 1 1 d . . . C3 C 0.28317(10) 0.55221(16) 0.68269(9) 0.0202(3) Uani 1 1 d . . . H2 H 0.3298 0.5463 0.7387 0.024 Uiso 1 1 calc R . . C4 C 0.31618(10) 0.61041(16) 0.60743(9) 0.0193(3) Uani 1 1 d . . . C5 C 0.24409(10) 0.61537(17) 0.52760(9) 0.0232(3) Uani 1 1 d . . . H3 H 0.2658 0.6548 0.4756 0.028 Uiso 1 1 calc R . . C6 C 0.14526(10) 0.44213(16) 0.75733(9) 0.0194(3) Uani 1 1 d . . . C7 C 0.12741(10) 0.55187(17) 0.82287(9) 0.0227(3) Uani 1 1 d . . . C8 C 0.09896(11) 0.49296(19) 0.90052(10) 0.0295(4) Uani 1 1 d . . . H4 H 0.0866 0.5657 0.9455 0.035 Uiso 1 1 calc R . . C9 C 0.08859(11) 0.3298(2) 0.91280(10) 0.0329(4) Uani 1 1 d . . . H5 H 0.0696 0.2912 0.9662 0.039 Uiso 1 1 calc R . . C10 C 0.10564(11) 0.22287(19) 0.84779(10) 0.0297(4) Uani 1 1 d . . . H6 H 0.0980 0.1111 0.8568 0.036 Uiso 1 1 calc R . . C11 C 0.13383(10) 0.27681(17) 0.76922(9) 0.0240(3) Uani 1 1 d . . . C12 C 0.13791(11) 0.72977(17) 0.80907(10) 0.0283(3) Uani 1 1 d . . . H7 H 0.2104 0.7566 0.8126 0.042 Uiso 1 1 calc R . . H8 H 0.1116 0.7883 0.8559 0.042 Uiso 1 1 calc R . . H9 H 0.0986 0.7601 0.7498 0.042 Uiso 1 1 calc R . . C13 C 0.15561(12) 0.15885(18) 0.70015(11) 0.0325(4) Uani 1 1 d . . . H10 H 0.1064 0.1749 0.6436 0.049 Uiso 1 1 calc R . . H11 H 0.1491 0.0493 0.7218 0.049 Uiso 1 1 calc R . . H12 H 0.2255 0.1755 0.6900 0.049 Uiso 1 1 calc R . . C14 C 0.42268(10) 0.67113(16) 0.61048(8) 0.0201(3) Uani 1 1 d . . . C15 C 0.50612(11) 0.56460(17) 0.62099(9) 0.0233(3) Uani 1 1 d . . . C16 C 0.60342(11) 0.62660(18) 0.62038(10) 0.0275(3) Uani 1 1 d . . . H13 H 0.6605 0.5558 0.6275 0.033 Uiso 1 1 calc R . . C17 C 0.61853(11) 0.78872(19) 0.60963(10) 0.0288(4) Uani 1 1 d . . . H14 H 0.6852 0.8286 0.6082 0.035 Uiso 1 1 calc R . . C18 C 0.53636(11) 0.89254(18) 0.60103(9) 0.0264(3) Uani 1 1 d . . . H15 H 0.5472 1.0042 0.5945 0.032 Uiso 1 1 calc R . . C19 C 0.43791(11) 0.83664(17) 0.60179(9) 0.0234(3) Uani 1 1 d . . . C20 C 0.35048(12) 0.95438(18) 0.59516(12) 0.0363(4) Uani 1 1 d . . . H16 H 0.3781 1.0631 0.6068 0.055 Uiso 1 1 calc R . . H17 H 0.3088 0.9270 0.6397 0.055 Uiso 1 1 calc R . . H18 H 0.3078 0.9496 0.5347 0.055 Uiso 1 1 calc R . . C21 C 0.49249(12) 0.38648(18) 0.63139(11) 0.0311(4) Uani 1 1 d . . . H19 H 0.5561 0.3310 0.6262 0.047 Uiso 1 1 calc R . . H20 H 0.4363 0.3483 0.5842 0.047 Uiso 1 1 calc R . . H21 H 0.4762 0.3644 0.6905 0.047 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 0.0233(6) 0.0300(7) 0.0194(6) 0.0008(5) 0.0038(5) -0.0022(5) C1 0.0192(7) 0.0223(7) 0.0207(7) -0.0013(5) 0.0042(5) -0.0017(5) C2 0.0212(7) 0.0155(7) 0.0197(7) -0.0004(5) 0.0053(5) -0.0002(5) C3 0.0218(7) 0.0201(7) 0.0175(7) -0.0002(5) 0.0012(5) 0.0006(5) C4 0.0199(7) 0.0178(7) 0.0202(7) -0.0004(5) 0.0044(5) 0.0000(5) C5 0.0241(7) 0.0268(8) 0.0198(7) 0.0022(6) 0.0068(6) -0.0008(6) C6 0.0143(6) 0.0252(7) 0.0181(7) 0.0027(5) 0.0019(5) -0.0014(5) C7 0.0169(7) 0.0306(8) 0.0197(7) 0.0008(6) 0.0011(5) 0.0011(6) C8 0.0243(8) 0.0437(10) 0.0209(7) -0.0005(6) 0.0050(6) 0.0026(7) C9 0.0245(8) 0.0501(10) 0.0251(8) 0.0126(7) 0.0071(6) -0.0006(7) C10 0.0241(8) 0.0324(9) 0.0325(8) 0.0116(7) 0.0052(6) -0.0032(6) C11 0.0175(7) 0.0276(8) 0.0263(7) 0.0042(6) 0.0026(6) -0.0016(6) C12 0.0300(8) 0.0298(8) 0.0245(8) -0.0058(6) 0.0036(6) 0.0001(6) C13 0.0384(9) 0.0226(8) 0.0376(9) 0.0014(6) 0.0105(7) -0.0020(7) C14 0.0209(7) 0.0249(8) 0.0147(6) -0.0003(5) 0.0041(5) -0.0018(6) C15 0.0235(7) 0.0261(8) 0.0197(7) -0.0010(6) 0.0030(5) 0.0007(6) C16 0.0203(7) 0.0337(9) 0.0278(8) -0.0003(6) 0.0031(6) 0.0028(6) C17 0.0211(8) 0.0390(9) 0.0255(8) -0.0017(6) 0.0027(6) -0.0077(6) C18 0.0279(8) 0.0259(8) 0.0251(7) 0.0001(6) 0.0042(6) -0.0070(6) C19 0.0246(8) 0.0247(8) 0.0214(7) 0.0008(6) 0.0059(6) -0.0014(6) C20 0.0319(9) 0.0251(8) 0.0549(11) 0.0026(7) 0.0154(8) 0.0016(7) C21 0.0301(8) 0.0271(8) 0.0359(9) 0.0015(7) 0.0057(7) 0.0024(6) _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 C1 1.3374(17) . ? N1 C5 1.3388(18) . ? C1 C2 1.3919(19) . ? C1 H1 0.9500 . ? C2 C3 1.3914(18) . ? C2 C6 1.4937(18) . ? C3 C4 1.3874(18) . ? C3 H2 0.9500 . ? C4 C5 1.3893(19) . ? C4 C14 1.4945(18) . ? C5 H3 0.9500 . ? C6 C11 1.401(2) . ? C6 C7 1.4043(19) . ? C7 C8 1.394(2) . ? C7 C12 1.507(2) . ? C8 C9 1.383(2) . ? C8 H4 0.9500 . ? C9 C10 1.380(2) . ? C9 H5 0.9500 . ? C10 C11 1.391(2) . ? C10 H6 0.9500 . ? C11 C13 1.505(2) . ? C12 H7 0.9800 . ? C12 H8 0.9800 . ? C12 H9 0.9800 . ? C13 H10 0.9800 . ? C13 H11 0.9800 . ? C13 H12 0.9800 . ? C14 C19 1.404(2) . ? C14 C15 1.405(2) . ? C15 C16 1.394(2) . ? C15 C21 1.507(2) . ? C16 C17 1.380(2) . ? C16 H13 0.9500 . ? C17 C18 1.379(2) . ? C17 H14 0.9500 . ? C18 C19 1.390(2) . ? C18 H15 0.9500 . ? C19 C20 1.509(2) . ? C20 H16 0.9800 . ? C20 H17 0.9800 . ? C20 H18 0.9800 . ? C21 H19 0.9800 . ? C21 H20 0.9800 . ? C21 H21 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 C1 N1 C5 116.72(11) . . ? N1 C1 C2 123.93(12) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C3 C2 C1 117.47(12) . . ? C3 C2 C6 120.67(11) . . ? C1 C2 C6 121.86(12) . . ? C4 C3 C2 120.25(12) . . ? C4 C3 H2 119.9 . . ? C2 C3 H2 119.9 . . ? C3 C4 C5 116.87(12) . . ? C3 C4 C14 122.84(12) . . ? C5 C4 C14 120.26(12) . . ? N1 C5 C4 124.76(12) . . ? N1 C5 H3 117.6 . . ? C4 C5 H3 117.6 . . ? C11 C6 C7 120.77(13) . . ? C11 C6 C2 119.87(12) . . ? C7 C6 C2 119.29(12) . . ? C8 C7 C6 118.64(13) . . ? C8 C7 C12 120.75(13) . . ? C6 C7 C12 120.61(12) . . ? C9 C8 C7 120.70(14) . . ? C9 C8 H4 119.7 . . ? C7 C8 H4 119.7 . . ? C10 C9 C8 120.29(14) . . ? C10 C9 H5 119.9 . . ? C8 C9 H5 119.9 . . ? C9 C10 C11 120.80(15) . . ? C9 C10 H6 119.6 . . ? C11 C10 H6 119.6 . . ? C10 C11 C6 118.81(14) . . ? C10 C11 C13 120.35(14) . . ? C6 C11 C13 120.80(12) . . ? C7 C12 H7 109.5 . . ? C7 C12 H8 109.5 . . ? H7 C12 H8 109.5 . . ? C7 C12 H9 109.5 . . ? H7 C12 H9 109.5 . . ? H8 C12 H9 109.5 . . ? C11 C13 H10 109.5 . . ? C11 C13 H11 109.5 . . ? H10 C13 H11 109.5 . . ? C11 C13 H12 109.5 . . ? H10 C13 H12 109.5 . . ? H11 C13 H12 109.5 . . ? C19 C14 C15 120.44(13) . . ? C19 C14 C4 118.85(12) . . ? C15 C14 C4 120.71(12) . . ? C16 C15 C14 118.50(13) . . ? C16 C15 C21 119.76(13) . . ? C14 C15 C21 121.73(13) . . ? C17 C16 C15 121.34(14) . . ? C17 C16 H13 119.3 . . ? C15 C16 H13 119.3 . . ? C18 C17 C16 119.65(13) . . ? C18 C17 H14 120.2 . . ? C16 C17 H14 120.2 . . ? C17 C18 C19 121.16(14) . . ? C17 C18 H15 119.4 . . ? C19 C18 H15 119.4 . . ? C18 C19 C14 118.88(13) . . ? C18 C19 C20 119.64(13) . . ? C14 C19 C20 121.47(13) . . ? C19 C20 H16 109.5 . . ? C19 C20 H17 109.5 . . ? H16 C20 H17 109.5 . . ? C19 C20 H18 109.5 . . ? H16 C20 H18 109.5 . . ? H17 C20 H18 109.5 . . ? C15 C21 H19 109.5 . . ? C15 C21 H20 109.5 . . ? H19 C21 H20 109.5 . . ? C15 C21 H21 109.5 . . ? H19 C21 H21 109.5 . . ? H20 C21 H21 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 C5 N1 C1 C2 0.3(2) . . . . ? N1 C1 C2 C3 -0.4(2) . . . . ? N1 C1 C2 C6 178.96(12) . . . . ? C1 C2 C3 C4 0.33(19) . . . . ? C6 C2 C3 C4 -179.03(12) . . . . ? C2 C3 C4 C5 -0.20(19) . . . . ? C2 C3 C4 C14 177.72(12) . . . . ? C1 N1 C5 C4 -0.1(2) . . . . ? C3 C4 C5 N1 0.1(2) . . . . ? C14 C4 C5 N1 -177.88(13) . . . . ? C3 C2 C6 C11 -102.16(15) . . . . ? C1 C2 C6 C11 78.50(17) . . . . ? C3 C2 C6 C7 74.74(17) . . . . ? C1 C2 C6 C7 -104.59(15) . . . . ? C11 C6 C7 C8 0.6(2) . . . . ? C2 C6 C7 C8 -176.28(12) . . . . ? C11 C6 C7 C12 -178.88(12) . . . . ? C2 C6 C7 C12 4.25(19) . . . . ? C6 C7 C8 C9 0.0(2) . . . . ? C12 C7 C8 C9 179.51(13) . . . . ? C7 C8 C9 C10 -0.5(2) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? C9 C10 C11 C6 0.4(2) . . . . ? C9 C10 C11 C13 177.98(14) . . . . ? C7 C6 C11 C10 -0.8(2) . . . . ? C2 C6 C11 C10 176.06(12) . . . . ? C7 C6 C11 C13 -178.39(12) . . . . ? C2 C6 C11 C13 -1.54(19) . . . . ? C3 C4 C14 C19 -108.49(15) . . . . ? C5 C4 C14 C19 69.36(17) . . . . ? C3 C4 C14 C15 72.11(18) . . . . ? C5 C4 C14 C15 -110.04(15) . . . . ? C19 C14 C15 C16 -1.5(2) . . . . ? C4 C14 C15 C16 177.86(12) . . . . ? C19 C14 C15 C21 179.40(13) . . . . ? C4 C14 C15 C21 -1.2(2) . . . . ? C14 C15 C16 C17 -0.1(2) . . . . ? C21 C15 C16 C17 179.00(13) . . . . ? C15 C16 C17 C18 1.3(2) . . . . ? C16 C17 C18 C19 -0.9(2) . . . . ? C17 C18 C19 C14 -0.7(2) . . . . ? C17 C18 C19 C20 178.07(14) . . . . ? C15 C14 C19 C18 1.9(2) . . . . ? C4 C14 C19 C18 -177.47(12) . . . . ? C15 C14 C19 C20 -176.85(13) . . . . ? C4 C14 C19 C20 3.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.154 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.036 data_compound3 _database_code_depnum_ccdc_archive 'CCDC 879860' #TrackingRef 'compound3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H40 F3 N O3 S' _chemical_formula_weight 647.77 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' F F 0.0171 0.0103 '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.1166(19) _cell_length_b 17.674(2) _cell_length_c 14.3488(19) _cell_angle_alpha 90.00 _cell_angle_beta 107.5846(18) _cell_angle_gamma 90.00 _cell_volume 3412.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 123.1500 _cell_measurement_reflns_used 8510 _cell_measurement_theta_min 3.0274 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9709 _exptl_absorpt_correction_T_max 0.9781 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22492 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5977 _reflns_number_gt 5211 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0552P)^2^+1.0200P] 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 5977 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.54465(9) 0.21119(7) 0.80357(9) 0.0182(3) Uani 1 1 d . . . C1 C 0.51074(12) 0.14043(9) 0.80910(11) 0.0186(3) Uani 1 1 d . . . H1 H 0.4630 0.1319 0.8426 0.022 Uiso 1 1 calc R . . C2 C 0.54466(11) 0.08014(9) 0.76659(11) 0.0187(3) Uani 1 1 d . . . C3 C 0.61367(12) 0.09495(9) 0.71693(11) 0.0205(3) Uani 1 1 d . . . H2 H 0.6387 0.0544 0.6878 0.025 Uiso 1 1 calc R . . C4 C 0.64652(11) 0.16844(9) 0.70944(11) 0.0201(3) Uani 1 1 d . . . C5 C 0.61143(11) 0.22571(9) 0.75541(11) 0.0200(3) Uani 1 1 d . . . H3 H 0.6345 0.2760 0.7532 0.024 Uiso 1 1 calc R . . C6 C 0.50711(11) 0.27378(8) 0.84971(11) 0.0180(3) Uani 1 1 d . . . C7 C 0.55949(11) 0.29283(9) 0.94527(11) 0.0196(3) Uani 1 1 d . . . C8 C 0.52125(12) 0.35178(9) 0.98770(12) 0.0222(4) Uani 1 1 d . . . H4 H 0.5558 0.3671 1.0525 0.027 Uiso 1 1 calc R . . C9 C 0.43362(12) 0.38869(9) 0.93726(12) 0.0219(4) Uani 1 1 d . . . C10 C 0.38533(12) 0.36750(9) 0.84154(12) 0.0227(4) Uani 1 1 d . . . H5 H 0.3259 0.3930 0.8068 0.027 Uiso 1 1 calc R . . C11 C 0.42105(12) 0.31027(9) 0.79481(12) 0.0210(4) Uani 1 1 d . . . C12 C 0.65325(13) 0.25270(10) 1.00163(12) 0.0272(4) Uani 1 1 d . . . H6 H 0.6392 0.1988 1.0068 0.041 Uiso 1 1 calc R . . H7 H 0.6783 0.2746 1.0673 0.041 Uiso 1 1 calc R . . H8 H 0.7034 0.2585 0.9675 0.041 Uiso 1 1 calc R . . C13 C 0.38896(14) 0.44823(10) 0.98647(14) 0.0305(4) Uani 1 1 d . . . H9 H 0.3357 0.4257 1.0081 0.046 Uiso 1 1 calc R . . H10 H 0.3617 0.4893 0.9402 0.046 Uiso 1 1 calc R . . H11 H 0.4404 0.4685 1.0431 0.046 Uiso 1 1 calc R . . C14 C 0.36888(13) 0.28967(10) 0.69028(13) 0.0306(4) Uani 1 1 d . . . H12 H 0.4126 0.3003 0.6502 0.046 Uiso 1 1 calc R . . H13 H 0.3079 0.3196 0.6663 0.046 Uiso 1 1 calc R . . H14 H 0.3521 0.2357 0.6861 0.046 Uiso 1 1 calc R . . C15 C 0.50592(12) 0.00292(9) 0.77561(12) 0.0206(4) Uani 1 1 d . . . C16 C 0.43771(12) -0.03097(10) 0.69383(13) 0.0248(4) Uani 1 1 d . . . C17 C 0.40014(13) -0.10183(10) 0.70582(15) 0.0331(4) Uani 1 1 d . . . H15 H 0.3535 -0.1255 0.6517 0.040 Uiso 1 1 calc R . . C18 C 0.42934(15) -0.13838(10) 0.79496(17) 0.0374(5) Uani 1 1 d . . . H16 H 0.4024 -0.1866 0.8019 0.045 Uiso 1 1 calc R . . C19 C 0.49755(15) -0.10501(10) 0.87382(15) 0.0347(5) Uani 1 1 d . . . H17 H 0.5181 -0.1310 0.9346 0.042 Uiso 1 1 calc R . . C20 C 0.53711(13) -0.03366(9) 0.86625(12) 0.0249(4) Uani 1 1 d . . . C21 C 0.40403(14) 0.00838(11) 0.59639(13) 0.0335(4) Uani 1 1 d . . . H18 H 0.3565 -0.0238 0.5491 0.050 Uiso 1 1 calc R . . H19 H 0.4616 0.0182 0.5734 0.050 Uiso 1 1 calc R . . H20 H 0.3721 0.0564 0.6032 0.050 Uiso 1 1 calc R . . C22 C 0.61314(15) 0.00061(11) 0.95271(13) 0.0349(4) Uani 1 1 d . . . H21 H 0.6708 0.0171 0.9334 0.052 Uiso 1 1 calc R . . H22 H 0.6342 -0.0371 1.0050 0.052 Uiso 1 1 calc R . . H23 H 0.5841 0.0442 0.9762 0.052 Uiso 1 1 calc R . . C23 C 0.71423(12) 0.18879(9) 0.65097(12) 0.0215(4) Uani 1 1 d . . . C24 C 0.67198(13) 0.21470(9) 0.55481(13) 0.0263(4) Uani 1 1 d . . . C25 C 0.73464(14) 0.23967(10) 0.50309(13) 0.0301(4) Uani 1 1 d . . . H24 H 0.7072 0.2575 0.4380 0.036 Uiso 1 1 calc R . . C26 C 0.83608(15) 0.23889(10) 0.54517(14) 0.0327(4) Uani 1 1 d . . . H25 H 0.8779 0.2574 0.5094 0.039 Uiso 1 1 calc R . . C27 C 0.87767(14) 0.21158(10) 0.63852(15) 0.0338(5) Uani 1 1 d . . . H26 H 0.9479 0.2101 0.6657 0.041 Uiso 1 1 calc R . . C28 C 0.81741(13) 0.18589(9) 0.69391(13) 0.0267(4) Uani 1 1 d . . . C29 C 0.56105(14) 0.21665(12) 0.50764(14) 0.0377(5) Uani 1 1 d . . . H27 H 0.5333 0.1663 0.5113 0.057 Uiso 1 1 calc R . . H28 H 0.5464 0.2316 0.4390 0.057 Uiso 1 1 calc R . . H29 H 0.5314 0.2532 0.5419 0.057 Uiso 1 1 calc R . . C30 C 0.86213(14) 0.15777(12) 0.79632(15) 0.0386(5) Uani 1 1 d . . . H30 H 0.8448 0.1923 0.8420 0.058 Uiso 1 1 calc R . . H31 H 0.9346 0.1554 0.8114 0.058 Uiso 1 1 calc R . . H32 H 0.8363 0.1072 0.8025 0.058 Uiso 1 1 calc R . . C31 C 0.15971(15) 0.05496(12) 0.81200(14) 0.0394(5) Uani 1 1 d . . . F1 F 0.13358(11) 0.07433(9) 0.89057(10) 0.0678(4) Uani 1 1 d . . . F2 F 0.07650(10) 0.03788(8) 0.74077(10) 0.0641(4) Uani 1 1 d . . . F3 F 0.21311(11) -0.00819(7) 0.83387(9) 0.0635(4) Uani 1 1 d . . . S1 S 0.22708(3) 0.13066(2) 0.77534(3) 0.02568(13) Uani 1 1 d . . . O1 O 0.31222(9) 0.14042(7) 0.86026(9) 0.0301(3) Uani 1 1 d . . . O2 O 0.15684(11) 0.19150(8) 0.75626(11) 0.0469(4) Uani 1 1 d . . . O3 O 0.24780(11) 0.10123(9) 0.69037(10) 0.0457(4) Uani 1 1 d . . . C32 C 0.65520(14) 0.42401(10) 0.69648(13) 0.0319(4) Uani 1 1 d . . . C33 C 0.74425(15) 0.39350(10) 0.69106(15) 0.0346(5) Uani 1 1 d . . . H33 H 0.7532 0.3849 0.6289 0.042 Uiso 1 1 calc R . . C34 C 0.81982(14) 0.37555(10) 0.77466(16) 0.0354(5) Uani 1 1 d . . . H34 H 0.8804 0.3551 0.7698 0.042 Uiso 1 1 calc R . . C35 C 0.80732(14) 0.38736(11) 0.86539(15) 0.0342(4) Uani 1 1 d . . . H35 H 0.8592 0.3748 0.9230 0.041 Uiso 1 1 calc R . . C36 C 0.71954(13) 0.41732(10) 0.87222(14) 0.0310(4) Uani 1 1 d . . . H36 H 0.7109 0.4253 0.9346 0.037 Uiso 1 1 calc R . . C37 C 0.64426(13) 0.43575(10) 0.78887(13) 0.0301(4) Uani 1 1 d . . . H37 H 0.5842 0.4567 0.7943 0.036 Uiso 1 1 calc R . . C38 C 0.57235(19) 0.44353(14) 0.60549(16) 0.0550(6) Uani 1 1 d . . . H38 H 0.5819 0.4951 0.5848 0.082 Uiso 1 1 calc R . . H39 H 0.5085 0.4403 0.6191 0.082 Uiso 1 1 calc R . . H40 H 0.5728 0.4079 0.5533 0.082 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 0.0190(7) 0.0163(7) 0.0193(7) -0.0012(5) 0.0057(5) 0.0001(5) C1 0.0184(8) 0.0192(8) 0.0182(8) 0.0010(6) 0.0057(6) -0.0022(6) C2 0.0187(8) 0.0176(8) 0.0185(8) -0.0007(6) 0.0036(6) -0.0005(6) C3 0.0214(8) 0.0188(8) 0.0209(8) -0.0026(7) 0.0056(7) 0.0009(7) C4 0.0187(8) 0.0204(8) 0.0211(8) -0.0002(7) 0.0059(7) -0.0009(7) C5 0.0203(8) 0.0194(8) 0.0214(8) 0.0006(7) 0.0078(7) -0.0031(7) C6 0.0190(8) 0.0147(8) 0.0222(8) -0.0012(6) 0.0092(7) -0.0011(6) C7 0.0196(8) 0.0185(8) 0.0213(8) -0.0002(6) 0.0071(7) -0.0031(7) C8 0.0238(9) 0.0229(8) 0.0212(8) -0.0029(7) 0.0089(7) -0.0035(7) C9 0.0236(9) 0.0172(8) 0.0282(9) -0.0003(7) 0.0127(7) -0.0027(7) C10 0.0180(8) 0.0198(8) 0.0309(9) 0.0033(7) 0.0083(7) 0.0013(7) C11 0.0188(8) 0.0204(8) 0.0234(8) 0.0002(7) 0.0060(7) -0.0038(7) C12 0.0247(9) 0.0291(9) 0.0249(9) -0.0030(7) 0.0031(7) 0.0039(8) C13 0.0347(10) 0.0246(9) 0.0376(10) -0.0023(8) 0.0190(8) 0.0032(8) C14 0.0276(10) 0.0321(10) 0.0270(9) -0.0024(8) 0.0006(8) 0.0008(8) C15 0.0201(8) 0.0172(8) 0.0278(9) -0.0008(7) 0.0124(7) 0.0010(7) C16 0.0215(9) 0.0239(9) 0.0315(9) -0.0072(7) 0.0120(7) -0.0005(7) C17 0.0265(10) 0.0253(10) 0.0519(12) -0.0139(9) 0.0187(9) -0.0066(8) C18 0.0407(11) 0.0165(9) 0.0665(14) -0.0030(9) 0.0334(11) -0.0039(8) C19 0.0458(12) 0.0211(9) 0.0471(12) 0.0099(8) 0.0288(10) 0.0081(8) C20 0.0290(9) 0.0207(9) 0.0286(9) 0.0020(7) 0.0142(8) 0.0047(7) C21 0.0293(10) 0.0405(11) 0.0282(10) -0.0086(8) 0.0048(8) -0.0019(8) C22 0.0444(11) 0.0328(10) 0.0270(10) 0.0070(8) 0.0098(9) 0.0045(9) C23 0.0255(9) 0.0152(8) 0.0287(9) -0.0042(7) 0.0156(7) -0.0023(7) C24 0.0335(10) 0.0216(9) 0.0284(9) -0.0026(7) 0.0163(8) -0.0023(7) C25 0.0446(11) 0.0216(9) 0.0305(10) -0.0029(7) 0.0208(9) -0.0033(8) C26 0.0437(12) 0.0212(9) 0.0437(11) -0.0072(8) 0.0289(10) -0.0077(8) C27 0.0269(10) 0.0266(10) 0.0549(13) -0.0126(9) 0.0230(9) -0.0058(8) C28 0.0260(9) 0.0195(8) 0.0372(10) -0.0061(7) 0.0133(8) -0.0017(7) C29 0.0364(11) 0.0483(12) 0.0290(10) 0.0060(9) 0.0106(8) 0.0003(9) C30 0.0275(10) 0.0415(11) 0.0447(12) -0.0001(9) 0.0079(9) 0.0022(9) C31 0.0412(11) 0.0424(12) 0.0313(10) -0.0043(9) 0.0058(9) -0.0133(10) F1 0.0713(10) 0.0940(11) 0.0508(8) -0.0113(7) 0.0376(7) -0.0406(8) F2 0.0464(8) 0.0763(10) 0.0583(9) -0.0110(7) -0.0013(6) -0.0311(7) F3 0.0948(11) 0.0270(7) 0.0485(8) 0.0045(6) -0.0084(7) -0.0116(7) S1 0.0268(2) 0.0255(2) 0.0257(2) 0.00342(17) 0.00929(18) 0.00376(18) O1 0.0224(6) 0.0346(7) 0.0332(7) -0.0019(6) 0.0084(5) -0.0023(5) O2 0.0478(9) 0.0363(8) 0.0504(9) 0.0061(7) 0.0056(7) 0.0202(7) O3 0.0539(9) 0.0600(10) 0.0285(7) 0.0001(7) 0.0203(7) 0.0095(8) C32 0.0414(11) 0.0221(9) 0.0324(10) -0.0004(8) 0.0115(9) -0.0018(8) C33 0.0481(12) 0.0247(9) 0.0412(11) -0.0078(8) 0.0287(10) -0.0102(9) C34 0.0287(10) 0.0277(10) 0.0565(13) -0.0089(9) 0.0230(10) -0.0025(8) C35 0.0268(10) 0.0295(10) 0.0428(11) -0.0042(9) 0.0052(8) 0.0003(8) C36 0.0338(10) 0.0305(10) 0.0317(10) -0.0041(8) 0.0144(8) 0.0001(8) C37 0.0282(10) 0.0265(9) 0.0376(10) -0.0047(8) 0.0132(8) 0.0045(8) C38 0.0672(16) 0.0503(14) 0.0391(12) 0.0017(11) 0.0035(11) 0.0094(12) _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 C1 1.350(2) . ? N1 C5 1.351(2) . ? N1 C6 1.4680(19) . ? C1 C2 1.383(2) . ? C1 H1 0.9500 . ? C2 C3 1.394(2) . ? C2 C15 1.490(2) . ? C3 C4 1.394(2) . ? C3 H2 0.9500 . ? C4 C5 1.379(2) . ? C4 C23 1.494(2) . ? C5 H3 0.9500 . ? C6 C7 1.388(2) . ? C6 C11 1.391(2) . ? C7 C8 1.395(2) . ? C7 C12 1.504(2) . ? C8 C9 1.392(2) . ? C8 H4 0.9500 . ? C9 C10 1.388(2) . ? C9 C13 1.507(2) . ? C10 C11 1.390(2) . ? C10 H5 0.9500 . ? C11 C14 1.502(2) . ? C12 H6 0.9800 . ? C12 H7 0.9800 . ? C12 H8 0.9800 . ? C13 H9 0.9800 . ? C13 H10 0.9800 . ? C13 H11 0.9800 . ? C14 H12 0.9800 . ? C14 H13 0.9800 . ? C14 H14 0.9800 . ? C15 C20 1.399(2) . ? C15 C16 1.407(2) . ? C16 C17 1.391(2) . ? C16 C21 1.504(3) . ? C17 C18 1.380(3) . ? C17 H15 0.9500 . ? C18 C19 1.377(3) . ? C18 H16 0.9500 . ? C19 C20 1.397(2) . ? C19 H17 0.9500 . ? C20 C22 1.501(3) . ? C21 H18 0.9800 . ? C21 H19 0.9800 . ? C21 H20 0.9800 . ? C22 H21 0.9800 . ? C22 H22 0.9800 . ? C22 H23 0.9800 . ? C23 C28 1.401(2) . ? C23 C24 1.404(2) . ? C24 C25 1.387(2) . ? C24 C29 1.507(3) . ? C25 C26 1.376(3) . ? C25 H24 0.9500 . ? C26 C27 1.377(3) . ? C26 H25 0.9500 . ? C27 C28 1.404(2) . ? C27 H26 0.9500 . ? C28 C30 1.498(3) . ? C29 H27 0.9800 . ? C29 H28 0.9800 . ? C29 H29 0.9800 . ? C30 H30 0.9800 . ? C30 H31 0.9800 . ? C30 H32 0.9800 . ? C31 F3 1.330(2) . ? C31 F1 1.332(2) . ? C31 F2 1.338(2) . ? C31 S1 1.809(2) . ? S1 O2 1.4320(13) . ? S1 O3 1.4346(14) . ? S1 O1 1.4402(13) . ? C32 C33 1.391(3) . ? C32 C37 1.396(3) . ? C32 C38 1.506(3) . ? C33 C34 1.380(3) . ? C33 H33 0.9500 . ? C34 C35 1.381(3) . ? C34 H34 0.9500 . ? C35 C36 1.378(3) . ? C35 H35 0.9500 . ? C36 C37 1.378(3) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 H38 0.9800 . ? C38 H39 0.9800 . ? C38 H40 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 C1 N1 C5 121.38(13) . . ? C1 N1 C6 119.27(13) . . ? C5 N1 C6 119.35(13) . . ? N1 C1 C2 120.77(14) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 117.97(14) . . ? C1 C2 C15 118.82(14) . . ? C3 C2 C15 123.21(14) . . ? C4 C3 C2 120.95(15) . . ? C4 C3 H2 119.5 . . ? C2 C3 H2 119.5 . . ? C5 C4 C3 118.10(14) . . ? C5 C4 C23 118.36(14) . . ? C3 C4 C23 123.49(14) . . ? N1 C5 C4 120.79(15) . . ? N1 C5 H3 119.6 . . ? C4 C5 H3 119.6 . . ? C7 C6 C11 124.08(14) . . ? C7 C6 N1 118.10(13) . . ? C11 C6 N1 117.82(14) . . ? C6 C7 C8 116.83(14) . . ? C6 C7 C12 122.43(14) . . ? C8 C7 C12 120.74(14) . . ? C9 C8 C7 121.55(15) . . ? C9 C8 H4 119.2 . . ? C7 C8 H4 119.2 . . ? C10 C9 C8 118.79(15) . . ? C10 C9 C13 120.14(15) . . ? C8 C9 C13 121.01(15) . . ? C9 C10 C11 122.19(15) . . ? C9 C10 H5 118.9 . . ? C11 C10 H5 118.9 . . ? C10 C11 C6 116.52(15) . . ? C10 C11 C14 121.21(15) . . ? C6 C11 C14 122.27(15) . . ? C7 C12 H6 109.5 . . ? C7 C12 H7 109.5 . . ? H6 C12 H7 109.5 . . ? C7 C12 H8 109.5 . . ? H6 C12 H8 109.5 . . ? H7 C12 H8 109.5 . . ? C9 C13 H9 109.5 . . ? C9 C13 H10 109.5 . . ? H9 C13 H10 109.5 . . ? C9 C13 H11 109.5 . . ? H9 C13 H11 109.5 . . ? H10 C13 H11 109.5 . . ? C11 C14 H12 109.5 . . ? C11 C14 H13 109.5 . . ? H12 C14 H13 109.5 . . ? C11 C14 H14 109.5 . . ? H12 C14 H14 109.5 . . ? H13 C14 H14 109.5 . . ? C20 C15 C16 121.49(15) . . ? C20 C15 C2 118.90(15) . . ? C16 C15 C2 119.60(15) . . ? C17 C16 C15 118.07(17) . . ? C17 C16 C21 120.40(16) . . ? C15 C16 C21 121.52(15) . . ? C18 C17 C16 121.19(18) . . ? C18 C17 H15 119.4 . . ? C16 C17 H15 119.4 . . ? C19 C18 C17 119.99(17) . . ? C19 C18 H16 120.0 . . ? C17 C18 H16 120.0 . . ? C18 C19 C20 121.30(18) . . ? C18 C19 H17 119.4 . . ? C20 C19 H17 119.4 . . ? C19 C20 C15 117.95(17) . . ? C19 C20 C22 120.20(16) . . ? C15 C20 C22 121.83(15) . . ? C16 C21 H18 109.5 . . ? C16 C21 H19 109.5 . . ? H18 C21 H19 109.5 . . ? C16 C21 H20 109.5 . . ? H18 C21 H20 109.5 . . ? H19 C21 H20 109.5 . . ? C20 C22 H21 109.5 . . ? C20 C22 H22 109.5 . . ? H21 C22 H22 109.5 . . ? C20 C22 H23 109.5 . . ? H21 C22 H23 109.5 . . ? H22 C22 H23 109.5 . . ? C28 C23 C24 121.38(15) . . ? C28 C23 C4 120.06(15) . . ? C24 C23 C4 118.46(15) . . ? C25 C24 C23 118.63(17) . . ? C25 C24 C29 119.77(16) . . ? C23 C24 C29 121.60(15) . . ? C26 C25 C24 120.62(18) . . ? C26 C25 H24 119.7 . . ? C24 C25 H24 119.7 . . ? C25 C26 C27 120.77(17) . . ? C25 C26 H25 119.6 . . ? C27 C26 H25 119.6 . . ? C26 C27 C28 120.73(18) . . ? C26 C27 H26 119.6 . . ? C28 C27 H26 119.6 . . ? C23 C28 C27 117.82(17) . . ? C23 C28 C30 121.18(16) . . ? C27 C28 C30 120.99(17) . . ? C24 C29 H27 109.5 . . ? C24 C29 H28 109.5 . . ? H27 C29 H28 109.5 . . ? C24 C29 H29 109.5 . . ? H27 C29 H29 109.5 . . ? H28 C29 H29 109.5 . . ? C28 C30 H30 109.5 . . ? C28 C30 H31 109.5 . . ? H30 C30 H31 109.5 . . ? C28 C30 H32 109.5 . . ? H30 C30 H32 109.5 . . ? H31 C30 H32 109.5 . . ? F3 C31 F1 107.34(17) . . ? F3 C31 F2 107.16(16) . . ? F1 C31 F2 107.50(17) . . ? F3 C31 S1 112.27(15) . . ? F1 C31 S1 111.11(14) . . ? F2 C31 S1 111.22(14) . . ? O2 S1 O3 114.64(9) . . ? O2 S1 O1 115.11(8) . . ? O3 S1 O1 115.48(8) . . ? O2 S1 C31 102.50(10) . . ? O3 S1 C31 103.83(9) . . ? O1 S1 C31 102.72(8) . . ? C33 C32 C37 118.14(18) . . ? C33 C32 C38 121.22(18) . . ? C37 C32 C38 120.64(18) . . ? C34 C33 C32 120.98(17) . . ? C34 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? C33 C34 C35 119.94(17) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C36 C35 C34 119.91(18) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C37 C36 C35 120.23(17) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C36 C37 C32 120.79(17) . . ? C36 C37 H37 119.6 . . ? C32 C37 H37 119.6 . . ? C32 C38 H38 109.5 . . ? C32 C38 H39 109.5 . . ? H38 C38 H39 109.5 . . ? C32 C38 H40 109.5 . . ? H38 C38 H40 109.5 . . ? H39 C38 H40 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 C5 N1 C1 C2 1.0(2) . . . . ? C6 N1 C1 C2 -179.89(14) . . . . ? N1 C1 C2 C3 -0.9(2) . . . . ? N1 C1 C2 C15 179.30(14) . . . . ? C1 C2 C3 C4 -0.7(2) . . . . ? C15 C2 C3 C4 179.09(15) . . . . ? C2 C3 C4 C5 2.2(2) . . . . ? C2 C3 C4 C23 -175.17(15) . . . . ? C1 N1 C5 C4 0.6(2) . . . . ? C6 N1 C5 C4 -178.57(14) . . . . ? C3 C4 C5 N1 -2.1(2) . . . . ? C23 C4 C5 N1 175.39(14) . . . . ? C1 N1 C6 C7 92.15(17) . . . . ? C5 N1 C6 C7 -88.69(18) . . . . ? C1 N1 C6 C11 -87.79(18) . . . . ? C5 N1 C6 C11 91.38(18) . . . . ? C11 C6 C7 C8 0.9(2) . . . . ? N1 C6 C7 C8 -179.07(13) . . . . ? C11 C6 C7 C12 -179.02(15) . . . . ? N1 C6 C7 C12 1.1(2) . . . . ? C6 C7 C8 C9 1.3(2) . . . . ? C12 C7 C8 C9 -178.84(15) . . . . ? C7 C8 C9 C10 -2.0(2) . . . . ? C7 C8 C9 C13 175.30(15) . . . . ? C8 C9 C10 C11 0.6(2) . . . . ? C13 C9 C10 C11 -176.71(15) . . . . ? C9 C10 C11 C6 1.4(2) . . . . ? C9 C10 C11 C14 -178.42(15) . . . . ? C7 C6 C11 C10 -2.1(2) . . . . ? N1 C6 C11 C10 177.79(13) . . . . ? C7 C6 C11 C14 177.63(15) . . . . ? N1 C6 C11 C14 -2.4(2) . . . . ? C1 C2 C15 C20 -72.3(2) . . . . ? C3 C2 C15 C20 107.87(18) . . . . ? C1 C2 C15 C16 106.53(18) . . . . ? C3 C2 C15 C16 -73.3(2) . . . . ? C20 C15 C16 C17 1.3(2) . . . . ? C2 C15 C16 C17 -177.55(14) . . . . ? C20 C15 C16 C21 179.91(15) . . . . ? C2 C15 C16 C21 1.1(2) . . . . ? C15 C16 C17 C18 -0.6(2) . . . . ? C21 C16 C17 C18 -179.25(17) . . . . ? C16 C17 C18 C19 -0.6(3) . . . . ? C17 C18 C19 C20 1.1(3) . . . . ? C18 C19 C20 C15 -0.5(3) . . . . ? C18 C19 C20 C22 -178.56(17) . . . . ? C16 C15 C20 C19 -0.7(2) . . . . ? C2 C15 C20 C19 178.07(14) . . . . ? C16 C15 C20 C22 177.31(15) . . . . ? C2 C15 C20 C22 -3.9(2) . . . . ? C5 C4 C23 C28 94.10(19) . . . . ? C3 C4 C23 C28 -88.5(2) . . . . ? C5 C4 C23 C24 -82.34(19) . . . . ? C3 C4 C23 C24 95.03(19) . . . . ? C28 C23 C24 C25 -1.7(2) . . . . ? C4 C23 C24 C25 174.65(15) . . . . ? C28 C23 C24 C29 178.91(16) . . . . ? C4 C23 C24 C29 -4.7(2) . . . . ? C23 C24 C25 C26 0.1(2) . . . . ? C29 C24 C25 C26 179.49(16) . . . . ? C24 C25 C26 C27 1.6(3) . . . . ? C25 C26 C27 C28 -1.8(3) . . . . ? C24 C23 C28 C27 1.6(2) . . . . ? C4 C23 C28 C27 -174.77(15) . . . . ? C24 C23 C28 C30 -179.64(16) . . . . ? C4 C23 C28 C30 4.0(2) . . . . ? C26 C27 C28 C23 0.2(2) . . . . ? C26 C27 C28 C30 -178.59(17) . . . . ? F3 C31 S1 O2 -179.74(13) . . . . ? F1 C31 S1 O2 -59.52(17) . . . . ? F2 C31 S1 O2 60.19(17) . . . . ? F3 C31 S1 O3 60.62(15) . . . . ? F1 C31 S1 O3 -179.16(14) . . . . ? F2 C31 S1 O3 -59.44(17) . . . . ? F3 C31 S1 O1 -60.02(15) . . . . ? F1 C31 S1 O1 60.19(16) . . . . ? F2 C31 S1 O1 179.91(14) . . . . ? C37 C32 C33 C34 -0.2(3) . . . . ? C38 C32 C33 C34 -179.84(18) . . . . ? C32 C33 C34 C35 0.4(3) . . . . ? C33 C34 C35 C36 -0.3(3) . . . . ? C34 C35 C36 C37 -0.2(3) . . . . ? C35 C36 C37 C32 0.4(3) . . . . ? C33 C32 C37 C36 -0.2(3) . . . . ? C38 C32 C37 C36 179.41(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.208 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.043 data_compound5 _database_code_depnum_ccdc_archive 'CCDC 879861' #TrackingRef 'compound5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H31 N S' _chemical_formula_weight 437.62 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' 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 P21/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 11.751(4) _cell_length_b 19.429(6) _cell_length_c 22.402(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.269(6) _cell_angle_gamma 90.00 _cell_volume 5074(3) _cell_formula_units_Z 8 _cell_measurement_temperature 123.1500 _cell_measurement_reflns_used 8601 _cell_measurement_theta_min 3.1625 _cell_measurement_theta_max 27.4372 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9857 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33370 _diffrn_reflns_av_R_equivalents 0.0760 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8903 _reflns_number_gt 5418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1475P)^2^+3.8073P] 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 8903 _refine_ls_number_parameters 591 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1590 _refine_ls_R_factor_gt 0.1084 _refine_ls_wR_factor_ref 0.3154 _refine_ls_wR_factor_gt 0.2705 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 0.8589(4) 0.1116(2) 0.11445(18) 0.0486(10) Uani 1 1 d . . . C1 C 0.8855(4) 0.1641(3) 0.0758(2) 0.0440(12) Uani 1 1 d . . . C2 C 0.9312(4) 0.2246(2) 0.1053(2) 0.0406(11) Uani 1 1 d . . . C3 C 0.9466(4) 0.2297(3) 0.1669(2) 0.0510(13) Uani 1 1 d . . . H1 H 0.9781 0.2708 0.1851 0.061 Uiso 1 1 calc R . . C4 C 0.9171(4) 0.1756(3) 0.2039(2) 0.0474(12) Uani 1 1 d . . . C5 C 0.8759(4) 0.1168(3) 0.1766(2) 0.0495(13) Uani 1 1 d . . . H2 H 0.8583 0.0788 0.2004 0.059 Uiso 1 1 calc R . . C6 C 0.8073(4) 0.0469(3) 0.0892(2) 0.0466(12) Uani 1 1 d . . . C7 C 0.6884(5) 0.0411(3) 0.0804(2) 0.0527(13) Uani 1 1 d . . . C8 C 0.6407(5) -0.0205(4) 0.0604(3) 0.0646(16) Uani 1 1 d . . . H3 H 0.5596 -0.0256 0.0555 0.077 Uiso 1 1 calc R . . C9 C 0.7104(5) -0.0765(3) 0.0469(3) 0.0597(15) Uani 1 1 d . . . C10 C 0.8280(5) -0.0692(3) 0.0564(2) 0.0570(14) Uani 1 1 d . . . H4 H 0.8753 -0.1070 0.0486 0.068 Uiso 1 1 calc R . . C11 C 0.8788(4) -0.0073(3) 0.0774(2) 0.0493(13) Uani 1 1 d . . . C12 C 0.6146(5) 0.1021(4) 0.0924(3) 0.0742(18) Uani 1 1 d . . . H5 H 0.5335 0.0898 0.0828 0.111 Uiso 1 1 calc R . . H6 H 0.6323 0.1409 0.0671 0.111 Uiso 1 1 calc R . . H7 H 0.6302 0.1151 0.1349 0.111 Uiso 1 1 calc R . . C13 C 0.6543(7) -0.1415(4) 0.0265(3) 0.097(2) Uani 1 1 d . . . H8 H 0.6483 -0.1444 -0.0174 0.145 Uiso 1 1 calc R . . H9 H 0.5773 -0.1431 0.0390 0.145 Uiso 1 1 calc R . . H10 H 0.6997 -0.1803 0.0445 0.145 Uiso 1 1 calc R . . C14 C 1.0074(5) 0.0014(3) 0.0863(3) 0.0584(14) Uani 1 1 d . . . H11 H 1.0286 0.0402 0.0620 0.088 Uiso 1 1 calc R . . H12 H 1.0437 -0.0408 0.0738 0.088 Uiso 1 1 calc R . . H13 H 1.0336 0.0103 0.1289 0.088 Uiso 1 1 calc R . . S1 S 0.86059(12) 0.15588(7) 0.00064(6) 0.0508(4) Uani 1 1 d . . . C15 C 0.9690(4) 0.2839(3) 0.0700(2) 0.0460(12) Uani 1 1 d . . . C16 C 1.0837(4) 0.2871(3) 0.0581(2) 0.0548(14) Uani 1 1 d . . . C17 C 1.1201(5) 0.3435(4) 0.0281(3) 0.0660(17) Uani 1 1 d . . . H14 H 1.1977 0.3461 0.0206 0.079 Uiso 1 1 calc R . . C18 C 1.0449(6) 0.3963(4) 0.0088(3) 0.0693(17) Uani 1 1 d . . . H15 H 1.0696 0.4347 -0.0125 0.083 Uiso 1 1 calc R . . C19 C 0.9325(5) 0.3913(3) 0.0214(3) 0.0644(16) Uani 1 1 d . . . H16 H 0.8808 0.4276 0.0089 0.077 Uiso 1 1 calc R . . C20 C 0.8925(5) 0.3360(3) 0.0514(2) 0.0535(13) Uani 1 1 d . . . C21 C 1.1656(5) 0.2289(4) 0.0796(3) 0.086(2) Uani 1 1 d . . . H17 H 1.2389 0.2358 0.0639 0.129 Uiso 1 1 calc R . . H18 H 1.1322 0.1848 0.0651 0.129 Uiso 1 1 calc R . . H19 H 1.1783 0.2286 0.1237 0.129 Uiso 1 1 calc R . . C22 C 0.7685(5) 0.3316(3) 0.0632(3) 0.081(2) Uani 1 1 d . . . H20 H 0.7634 0.3434 0.1053 0.122 Uiso 1 1 calc R . . H21 H 0.7400 0.2847 0.0552 0.122 Uiso 1 1 calc R . . H22 H 0.7220 0.3639 0.0368 0.122 Uiso 1 1 calc R . . C23 C 0.9315(5) 0.1853(3) 0.2709(2) 0.0506(13) Uani 1 1 d . . . C24 C 1.0375(5) 0.1712(3) 0.3049(2) 0.0556(14) Uani 1 1 d . . . C25 C 1.0481(5) 0.1845(3) 0.3666(2) 0.0629(16) Uani 1 1 d . . . H23 H 1.1189 0.1747 0.3905 0.075 Uiso 1 1 calc R . . C26 C 0.9592(6) 0.2113(3) 0.3940(2) 0.0661(17) Uani 1 1 d . . . H24 H 0.9692 0.2208 0.4359 0.079 Uiso 1 1 calc R . . C27 C 0.8559(6) 0.2243(3) 0.3598(3) 0.0649(16) Uani 1 1 d . . . H25 H 0.7942 0.2417 0.3789 0.078 Uiso 1 1 calc R . . C28 C 0.8391(5) 0.2127(3) 0.2975(2) 0.0552(14) Uani 1 1 d . . . C29 C 1.1360(5) 0.1428(3) 0.2762(3) 0.0672(16) Uani 1 1 d . . . H26 H 1.1112 0.1013 0.2533 0.101 Uiso 1 1 calc R . . H27 H 1.1991 0.1313 0.3074 0.101 Uiso 1 1 calc R . . H28 H 1.1619 0.1774 0.2490 0.101 Uiso 1 1 calc R . . C30 C 0.7273(5) 0.2314(3) 0.2601(3) 0.0682(17) Uani 1 1 d . . . H29 H 0.7368 0.2745 0.2386 0.102 Uiso 1 1 calc R . . H30 H 0.6674 0.2371 0.2864 0.102 Uiso 1 1 calc R . . H31 H 0.7051 0.1947 0.2310 0.102 Uiso 1 1 calc R . . N2 N 0.5986(3) -0.0843(2) 0.34787(18) 0.0465(10) Uani 1 1 d . . . C31 C 0.5101(4) -0.0562(3) 0.3092(2) 0.0481(13) Uani 1 1 d . . . C32 C 0.5410(4) -0.0349(3) 0.2520(2) 0.0479(13) Uani 1 1 d . . . C33 C 0.6503(4) -0.0418(3) 0.2382(2) 0.0517(13) Uani 1 1 d . . . H32 H 0.6678 -0.0267 0.2000 0.062 Uiso 1 1 calc R . . C34 C 0.7393(4) -0.0712(3) 0.2802(2) 0.0472(12) Uani 1 1 d . . . C35 C 0.7091(4) -0.0923(3) 0.3338(2) 0.0486(13) Uani 1 1 d . . . H33 H 0.7653 -0.1131 0.3624 0.058 Uiso 1 1 calc R . . C36 C 0.5800(4) -0.1089(3) 0.4078(2) 0.0496(13) Uani 1 1 d . . . C37 C 0.5417(4) -0.1767(3) 0.4137(2) 0.0492(13) Uani 1 1 d . . . C38 C 0.5309(5) -0.1985(3) 0.4719(3) 0.0631(16) Uani 1 1 d . . . H34 H 0.5051 -0.2441 0.4777 0.076 Uiso 1 1 calc R . . C39 C 0.5562(5) -0.1563(4) 0.5218(3) 0.0735(19) Uani 1 1 d . . . C40 C 0.5915(5) -0.0895(4) 0.5127(3) 0.0759(19) Uani 1 1 d . . . H35 H 0.6066 -0.0599 0.5465 0.091 Uiso 1 1 calc R . . C41 C 0.6056(5) -0.0644(3) 0.4561(3) 0.0593(15) Uani 1 1 d . . . C42 C 0.5139(5) -0.2221(3) 0.3596(3) 0.0594(15) Uani 1 1 d . . . H36 H 0.4485 -0.2030 0.3334 0.089 Uiso 1 1 calc R . . H37 H 0.4946 -0.2684 0.3727 0.089 Uiso 1 1 calc R . . H38 H 0.5805 -0.2248 0.3374 0.089 Uiso 1 1 calc R . . C43 C 0.5392(8) -0.1836(5) 0.5839(3) 0.117(3) Uani 1 1 d . . . H39 H 0.4577 -0.1935 0.5851 0.176 Uiso 1 1 calc R . . H40 H 0.5650 -0.1490 0.6145 0.176 Uiso 1 1 calc R . . H41 H 0.5839 -0.2259 0.5921 0.176 Uiso 1 1 calc R . . C44 C 0.6470(6) 0.0083(3) 0.4470(3) 0.082(2) Uani 1 1 d . . . H42 H 0.7240 0.0067 0.4346 0.122 Uiso 1 1 calc R . . H43 H 0.6495 0.0339 0.4848 0.122 Uiso 1 1 calc R . . H44 H 0.5943 0.0311 0.4158 0.122 Uiso 1 1 calc R . . S2 S 0.37836(11) -0.04837(8) 0.33004(7) 0.0608(5) Uani 1 1 d . . . C45 C 0.4512(4) -0.0050(3) 0.2054(2) 0.0512(13) Uani 1 1 d . . . C46 C 0.4211(4) 0.0647(3) 0.2085(3) 0.0527(13) Uani 1 1 d . . . C47 C 0.3414(5) 0.0919(3) 0.1633(3) 0.0608(15) Uani 1 1 d . . . H45 H 0.3200 0.1389 0.1650 0.073 Uiso 1 1 calc R . . C48 C 0.2933(5) 0.0521(3) 0.1165(3) 0.0624(16) Uani 1 1 d . . . H46 H 0.2392 0.0719 0.0863 0.075 Uiso 1 1 calc R . . C49 C 0.3220(4) -0.0154(4) 0.1126(3) 0.0630(16) Uani 1 1 d . . . H47 H 0.2885 -0.0421 0.0795 0.076 Uiso 1 1 calc R . . C50 C 0.4011(4) -0.0460(3) 0.1574(3) 0.0534(13) Uani 1 1 d . . . C51 C 0.4724(6) 0.1090(3) 0.2593(3) 0.0740(18) Uani 1 1 d . . . H48 H 0.4570 0.1574 0.2493 0.111 Uiso 1 1 calc R . . H49 H 0.5554 0.1013 0.2664 0.111 Uiso 1 1 calc R . . H50 H 0.4384 0.0972 0.2958 0.111 Uiso 1 1 calc R . . C52 C 0.4301(5) -0.1218(3) 0.1547(3) 0.0695(17) Uani 1 1 d . . . H51 H 0.5081 -0.1270 0.1441 0.104 Uiso 1 1 calc R . . H52 H 0.3756 -0.1444 0.1241 0.104 Uiso 1 1 calc R . . H53 H 0.4254 -0.1429 0.1940 0.104 Uiso 1 1 calc R . . C53 C 0.8598(4) -0.0798(3) 0.2649(3) 0.0563(15) Uani 1 1 d . . . C54 C 0.9493(5) -0.0426(3) 0.2971(3) 0.0649(17) Uani 1 1 d . . . C55 C 1.0599(5) -0.0519(4) 0.2803(4) 0.077(2) Uani 1 1 d . . . H54 H 1.1223 -0.0268 0.3010 0.093 Uiso 1 1 calc R . . C56 C 1.0800(6) -0.0956(4) 0.2356(4) 0.087(2) Uani 1 1 d . . . H55 H 1.1555 -0.1010 0.2253 0.105 Uiso 1 1 calc R . . C57 C 0.9907(5) -0.1319(4) 0.2055(3) 0.0737(19) Uani 1 1 d . . . H56 H 1.0050 -0.1619 0.1738 0.088 Uiso 1 1 calc R . . C58 C 0.8802(5) -0.1259(3) 0.2200(3) 0.0597(15) Uani 1 1 d . . . C59 C 0.9276(5) 0.0071(3) 0.3456(3) 0.0726(18) Uani 1 1 d . . . H57 H 0.8603 0.0353 0.3317 0.109 Uiso 1 1 calc R . . H58 H 0.9947 0.0369 0.3552 0.109 Uiso 1 1 calc R . . H59 H 0.9136 -0.0185 0.3817 0.109 Uiso 1 1 calc R . . C60 C 0.7839(5) -0.1700(3) 0.1868(3) 0.0688(17) Uani 1 1 d . . . H60 H 0.7451 -0.1954 0.2162 0.103 Uiso 1 1 calc R . . H61 H 0.8166 -0.2025 0.1602 0.103 Uiso 1 1 calc R . . H62 H 0.7284 -0.1401 0.1628 0.103 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 0.049(3) 0.052(3) 0.044(2) -0.003(2) 0.0064(19) 0.005(2) C1 0.035(3) 0.051(3) 0.047(3) 0.001(2) 0.010(2) 0.008(2) C2 0.041(3) 0.046(3) 0.035(3) -0.002(2) 0.004(2) 0.009(2) C3 0.054(3) 0.053(3) 0.046(3) -0.006(2) 0.006(2) 0.007(3) C4 0.049(3) 0.051(3) 0.042(3) 0.000(2) 0.003(2) 0.006(2) C5 0.049(3) 0.058(3) 0.041(3) 0.002(2) 0.004(2) 0.008(3) C6 0.046(3) 0.057(3) 0.037(3) -0.005(2) 0.006(2) -0.003(3) C7 0.045(3) 0.063(4) 0.052(3) 0.006(3) 0.014(2) 0.005(3) C8 0.046(3) 0.089(5) 0.061(4) 0.011(3) 0.012(3) -0.009(3) C9 0.056(4) 0.062(4) 0.061(4) 0.003(3) 0.004(3) -0.015(3) C10 0.059(4) 0.054(3) 0.059(3) 0.003(3) 0.012(3) -0.006(3) C11 0.045(3) 0.062(3) 0.041(3) 0.006(2) 0.006(2) 0.002(3) C12 0.053(4) 0.095(5) 0.075(4) 0.002(4) 0.011(3) 0.016(3) C13 0.108(6) 0.102(6) 0.081(5) -0.008(4) 0.018(4) -0.032(5) C14 0.053(3) 0.054(3) 0.067(4) -0.004(3) 0.003(3) 0.003(3) S1 0.0581(8) 0.0543(8) 0.0394(7) -0.0020(6) 0.0041(6) -0.0038(6) C15 0.042(3) 0.058(3) 0.037(3) -0.004(2) 0.002(2) 0.004(2) C16 0.041(3) 0.076(4) 0.046(3) -0.013(3) -0.002(2) -0.002(3) C17 0.047(3) 0.092(5) 0.060(4) -0.011(3) 0.009(3) -0.017(3) C18 0.068(4) 0.082(4) 0.057(4) -0.002(3) 0.003(3) -0.026(4) C19 0.062(4) 0.067(4) 0.063(4) 0.007(3) 0.005(3) -0.004(3) C20 0.055(3) 0.057(3) 0.049(3) 0.000(3) 0.007(2) 0.006(3) C21 0.045(4) 0.112(6) 0.100(5) -0.008(4) 0.009(3) 0.010(4) C22 0.050(4) 0.070(4) 0.128(6) 0.019(4) 0.023(4) 0.023(3) C23 0.058(3) 0.045(3) 0.049(3) -0.003(2) 0.008(2) -0.001(3) C24 0.062(3) 0.065(4) 0.038(3) 0.002(3) 0.003(2) 0.006(3) C25 0.076(4) 0.066(4) 0.044(3) -0.001(3) -0.005(3) 0.010(3) C26 0.103(5) 0.066(4) 0.029(3) -0.005(3) 0.005(3) 0.014(4) C27 0.079(4) 0.070(4) 0.049(3) 0.005(3) 0.019(3) 0.008(3) C28 0.068(4) 0.058(3) 0.041(3) -0.001(2) 0.013(3) 0.004(3) C29 0.063(4) 0.079(4) 0.059(4) 0.001(3) 0.002(3) 0.010(3) C30 0.061(4) 0.086(5) 0.057(4) -0.010(3) 0.007(3) 0.012(3) N2 0.033(2) 0.053(3) 0.053(3) 0.005(2) 0.0033(18) -0.0027(19) C31 0.032(3) 0.057(3) 0.053(3) 0.006(3) 0.001(2) 0.000(2) C32 0.031(3) 0.044(3) 0.068(3) 0.004(2) 0.004(2) 0.000(2) C33 0.038(3) 0.058(3) 0.059(3) 0.012(3) 0.006(2) 0.002(2) C34 0.034(3) 0.055(3) 0.052(3) 0.007(2) 0.002(2) -0.006(2) C35 0.030(3) 0.051(3) 0.064(3) 0.004(3) 0.002(2) -0.003(2) C36 0.029(3) 0.064(4) 0.056(3) 0.002(3) 0.005(2) 0.006(2) C37 0.032(3) 0.063(3) 0.052(3) 0.007(3) 0.004(2) 0.003(2) C38 0.048(3) 0.075(4) 0.066(4) 0.018(3) 0.011(3) 0.013(3) C39 0.060(4) 0.108(6) 0.054(4) 0.013(4) 0.014(3) 0.028(4) C40 0.060(4) 0.101(6) 0.066(4) -0.019(4) 0.002(3) 0.023(4) C41 0.042(3) 0.070(4) 0.066(4) -0.012(3) 0.005(3) 0.010(3) C42 0.056(3) 0.053(3) 0.067(4) -0.005(3) 0.001(3) -0.007(3) C43 0.142(8) 0.155(8) 0.059(5) 0.020(5) 0.030(5) 0.042(6) C44 0.071(4) 0.068(4) 0.104(5) -0.036(4) 0.005(4) -0.002(3) S2 0.0343(7) 0.0803(10) 0.0683(10) 0.0138(8) 0.0082(6) 0.0053(7) C45 0.027(2) 0.062(3) 0.064(3) 0.010(3) 0.007(2) 0.003(2) C46 0.037(3) 0.056(3) 0.065(4) 0.007(3) 0.006(2) 0.001(2) C47 0.041(3) 0.068(4) 0.072(4) 0.014(3) 0.002(3) 0.012(3) C48 0.037(3) 0.084(5) 0.066(4) 0.017(3) 0.004(3) 0.008(3) C49 0.038(3) 0.095(5) 0.056(3) 0.002(3) 0.005(2) 0.004(3) C50 0.038(3) 0.063(3) 0.060(3) -0.003(3) 0.006(2) -0.002(3) C51 0.067(4) 0.063(4) 0.090(5) 0.000(3) 0.000(3) 0.004(3) C52 0.060(4) 0.069(4) 0.078(4) 0.002(3) -0.001(3) -0.007(3) C53 0.035(3) 0.075(4) 0.058(3) 0.025(3) 0.004(2) 0.004(3) C54 0.042(3) 0.079(4) 0.071(4) 0.031(3) 0.000(3) 0.000(3) C55 0.033(3) 0.092(5) 0.103(5) 0.036(4) -0.008(3) -0.007(3) C56 0.042(4) 0.114(6) 0.109(6) 0.050(5) 0.019(4) 0.018(4) C57 0.045(4) 0.098(5) 0.079(4) 0.026(4) 0.014(3) 0.020(3) C58 0.044(3) 0.072(4) 0.064(4) 0.022(3) 0.010(3) 0.006(3) C59 0.049(3) 0.074(4) 0.091(5) 0.018(4) -0.007(3) -0.024(3) C60 0.056(4) 0.079(4) 0.074(4) 0.006(3) 0.015(3) 0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.385(6) . ? N1 C1 1.398(6) . ? N1 C6 1.477(6) . ? C1 C2 1.420(7) . ? C1 S1 1.680(5) . ? C2 C3 1.372(6) . ? C2 C15 1.498(7) . ? C3 C4 1.408(7) . ? C3 H1 0.9500 . ? C4 C5 1.356(7) . ? C4 C23 1.501(7) . ? C5 H2 0.9500 . ? C6 C7 1.391(7) . ? C6 C11 1.393(7) . ? C7 C8 1.371(8) . ? C7 C12 1.513(8) . ? C8 C9 1.418(8) . ? C8 H3 0.9500 . ? C9 C10 1.378(8) . ? C9 C13 1.470(9) . ? C10 C11 1.399(7) . ? C10 H4 0.9500 . ? C11 C14 1.509(7) . ? C12 H5 0.9800 . ? C12 H6 0.9800 . ? C12 H7 0.9800 . ? C13 H8 0.9800 . ? C13 H9 0.9800 . ? C13 H10 0.9800 . ? C14 H11 0.9800 . ? C14 H12 0.9800 . ? C14 H13 0.9800 . ? C15 C20 1.382(7) . ? C15 C16 1.408(7) . ? C16 C17 1.380(8) . ? C16 C21 1.524(9) . ? C17 C18 1.387(9) . ? C17 H14 0.9500 . ? C18 C19 1.389(8) . ? C18 H15 0.9500 . ? C19 C20 1.381(8) . ? C19 H16 0.9500 . ? C20 C22 1.516(8) . ? C21 H17 0.9800 . ? C21 H18 0.9800 . ? C21 H19 0.9800 . ? C22 H20 0.9800 . ? C22 H21 0.9800 . ? C22 H22 0.9800 . ? C23 C24 1.403(7) . ? C23 C28 1.408(7) . ? C24 C25 1.395(7) . ? C24 C29 1.499(8) . ? C25 C26 1.380(8) . ? C25 H23 0.9500 . ? C26 C27 1.374(8) . ? C26 H24 0.9500 . ? C27 C28 1.401(7) . ? C27 H25 0.9500 . ? C28 C30 1.511(8) . ? C29 H26 0.9800 . ? C29 H27 0.9800 . ? C29 H28 0.9800 . ? C30 H29 0.9800 . ? C30 H30 0.9800 . ? C30 H31 0.9800 . ? N2 C31 1.380(6) . ? N2 C35 1.382(6) . ? N2 C36 1.466(6) . ? C31 C32 1.436(7) . ? C31 S2 1.679(5) . ? C32 C33 1.366(7) . ? C32 C45 1.503(7) . ? C33 C34 1.434(7) . ? C33 H32 0.9500 . ? C34 C35 1.359(7) . ? C34 C53 1.507(7) . ? C35 H33 0.9500 . ? C36 C41 1.389(8) . ? C36 C37 1.403(7) . ? C37 C38 1.391(7) . ? C37 C42 1.502(7) . ? C38 C39 1.388(9) . ? C38 H34 0.9500 . ? C39 C40 1.384(10) . ? C39 C43 1.526(9) . ? C40 C41 1.390(9) . ? C40 H35 0.9500 . ? C41 C44 1.515(9) . ? C42 H36 0.9800 . ? C42 H37 0.9800 . ? C42 H38 0.9800 . ? C43 H39 0.9800 . ? C43 H40 0.9800 . ? C43 H41 0.9800 . ? C44 H42 0.9800 . ? C44 H43 0.9800 . ? C44 H44 0.9800 . ? C45 C46 1.403(8) . ? C45 C50 1.407(8) . ? C46 C47 1.395(7) . ? C46 C51 1.491(8) . ? C47 C48 1.365(8) . ? C47 H45 0.9500 . ? C48 C49 1.360(9) . ? C48 H46 0.9500 . ? C49 C50 1.410(8) . ? C49 H47 0.9500 . ? C50 C52 1.514(8) . ? C51 H48 0.9800 . ? C51 H49 0.9800 . ? C51 H50 0.9800 . ? C52 H51 0.9800 . ? C52 H52 0.9800 . ? C52 H53 0.9800 . ? C53 C58 1.390(8) . ? C53 C54 1.399(8) . ? C54 C55 1.409(9) . ? C54 C59 1.500(9) . ? C55 C56 1.357(10) . ? C55 H54 0.9500 . ? C56 C57 1.370(10) . ? C56 H55 0.9500 . ? C57 C58 1.383(8) . ? C57 H56 0.9500 . ? C58 C60 1.534(8) . ? C59 H57 0.9800 . ? C59 H58 0.9800 . ? C59 H59 0.9800 . ? C60 H60 0.9800 . ? C60 H61 0.9800 . ? C60 H62 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 C5 N1 C1 123.7(4) . . ? C5 N1 C6 116.6(4) . . ? C1 N1 C6 119.8(4) . . ? N1 C1 C2 114.6(4) . . ? N1 C1 S1 121.8(4) . . ? C2 C1 S1 123.6(4) . . ? C3 C2 C1 121.5(5) . . ? C3 C2 C15 117.7(4) . . ? C1 C2 C15 120.7(4) . . ? C2 C3 C4 121.8(5) . . ? C2 C3 H1 119.1 . . ? C4 C3 H1 119.1 . . ? C5 C4 C3 117.6(5) . . ? C5 C4 C23 123.1(5) . . ? C3 C4 C23 119.4(5) . . ? C4 C5 N1 120.8(5) . . ? C4 C5 H2 119.6 . . ? N1 C5 H2 119.6 . . ? C7 C6 C11 122.0(5) . . ? C7 C6 N1 118.7(5) . . ? C11 C6 N1 119.2(4) . . ? C8 C7 C6 118.6(5) . . ? C8 C7 C12 121.4(5) . . ? C6 C7 C12 119.9(5) . . ? C7 C8 C9 121.0(5) . . ? C7 C8 H3 119.5 . . ? C9 C8 H3 119.5 . . ? C10 C9 C8 118.9(5) . . ? C10 C9 C13 122.6(6) . . ? C8 C9 C13 118.4(6) . . ? C9 C10 C11 121.2(5) . . ? C9 C10 H4 119.4 . . ? C11 C10 H4 119.4 . . ? C6 C11 C10 118.2(5) . . ? C6 C11 C14 120.6(5) . . ? C10 C11 C14 121.2(5) . . ? C7 C12 H5 109.5 . . ? C7 C12 H6 109.5 . . ? H5 C12 H6 109.5 . . ? C7 C12 H7 109.5 . . ? H5 C12 H7 109.5 . . ? H6 C12 H7 109.5 . . ? C9 C13 H8 109.5 . . ? C9 C13 H9 109.5 . . ? H8 C13 H9 109.5 . . ? C9 C13 H10 109.5 . . ? H8 C13 H10 109.5 . . ? H9 C13 H10 109.5 . . ? C11 C14 H11 109.5 . . ? C11 C14 H12 109.5 . . ? H11 C14 H12 109.5 . . ? C11 C14 H13 109.5 . . ? H11 C14 H13 109.5 . . ? H12 C14 H13 109.5 . . ? C20 C15 C16 120.8(5) . . ? C20 C15 C2 119.8(4) . . ? C16 C15 C2 119.3(5) . . ? C17 C16 C15 119.4(5) . . ? C17 C16 C21 121.4(5) . . ? C15 C16 C21 119.2(5) . . ? C16 C17 C18 121.0(5) . . ? C16 C17 H14 119.5 . . ? C18 C17 H14 119.5 . . ? C17 C18 C19 118.0(6) . . ? C17 C18 H15 121.0 . . ? C19 C18 H15 121.0 . . ? C20 C19 C18 123.0(6) . . ? C20 C19 H16 118.5 . . ? C18 C19 H16 118.5 . . ? C19 C20 C15 117.9(5) . . ? C19 C20 C22 121.5(5) . . ? C15 C20 C22 120.6(5) . . ? C16 C21 H17 109.5 . . ? C16 C21 H18 109.5 . . ? H17 C21 H18 109.5 . . ? C16 C21 H19 109.5 . . ? H17 C21 H19 109.5 . . ? H18 C21 H19 109.5 . . ? C20 C22 H20 109.5 . . ? C20 C22 H21 109.5 . . ? H20 C22 H21 109.5 . . ? C20 C22 H22 109.5 . . ? H20 C22 H22 109.5 . . ? H21 C22 H22 109.5 . . ? C24 C23 C28 121.5(5) . . ? C24 C23 C4 120.0(5) . . ? C28 C23 C4 118.4(5) . . ? C25 C24 C23 117.7(5) . . ? C25 C24 C29 121.1(5) . . ? C23 C24 C29 121.2(5) . . ? C26 C25 C24 122.1(5) . . ? C26 C25 H23 118.9 . . ? C24 C25 H23 118.9 . . ? C27 C26 C25 119.1(5) . . ? C27 C26 H24 120.4 . . ? C25 C26 H24 120.4 . . ? C26 C27 C28 121.9(6) . . ? C26 C27 H25 119.0 . . ? C28 C27 H25 119.0 . . ? C27 C28 C23 117.6(5) . . ? C27 C28 C30 121.1(5) . . ? C23 C28 C30 121.2(5) . . ? C24 C29 H26 109.5 . . ? C24 C29 H27 109.5 . . ? H26 C29 H27 109.5 . . ? C24 C29 H28 109.5 . . ? H26 C29 H28 109.5 . . ? H27 C29 H28 109.5 . . ? C28 C30 H29 109.5 . . ? C28 C30 H30 109.5 . . ? H29 C30 H30 109.5 . . ? C28 C30 H31 109.5 . . ? H29 C30 H31 109.5 . . ? H30 C30 H31 109.5 . . ? C31 N2 C35 123.8(4) . . ? C31 N2 C36 121.0(4) . . ? C35 N2 C36 115.2(4) . . ? N2 C31 C32 114.8(4) . . ? N2 C31 S2 120.6(4) . . ? C32 C31 S2 124.6(4) . . ? C33 C32 C31 121.7(5) . . ? C33 C32 C45 118.6(5) . . ? C31 C32 C45 119.7(4) . . ? C32 C33 C34 121.3(5) . . ? C32 C33 H32 119.4 . . ? C34 C33 H32 119.4 . . ? C35 C34 C33 116.7(5) . . ? C35 C34 C53 121.7(4) . . ? C33 C34 C53 121.5(4) . . ? C34 C35 N2 121.7(5) . . ? C34 C35 H33 119.1 . . ? N2 C35 H33 119.1 . . ? C41 C36 C37 123.4(5) . . ? C41 C36 N2 117.9(5) . . ? C37 C36 N2 118.6(5) . . ? C38 C37 C36 116.3(5) . . ? C38 C37 C42 122.7(5) . . ? C36 C37 C42 121.0(5) . . ? C39 C38 C37 122.6(6) . . ? C39 C38 H34 118.7 . . ? C37 C38 H34 118.7 . . ? C40 C39 C38 118.2(6) . . ? C40 C39 C43 122.4(7) . . ? C38 C39 C43 119.3(8) . . ? C39 C40 C41 122.4(6) . . ? C39 C40 H35 118.8 . . ? C41 C40 H35 118.8 . . ? C36 C41 C40 117.0(6) . . ? C36 C41 C44 121.1(6) . . ? C40 C41 C44 121.9(6) . . ? C37 C42 H36 109.5 . . ? C37 C42 H37 109.5 . . ? H36 C42 H37 109.5 . . ? C37 C42 H38 109.5 . . ? H36 C42 H38 109.5 . . ? H37 C42 H38 109.5 . . ? C39 C43 H39 109.5 . . ? C39 C43 H40 109.5 . . ? H39 C43 H40 109.5 . . ? C39 C43 H41 109.5 . . ? H39 C43 H41 109.5 . . ? H40 C43 H41 109.5 . . ? C41 C44 H42 109.5 . . ? C41 C44 H43 109.5 . . ? H42 C44 H43 109.5 . . ? C41 C44 H44 109.5 . . ? H42 C44 H44 109.5 . . ? H43 C44 H44 109.5 . . ? C46 C45 C50 120.1(5) . . ? C46 C45 C32 119.9(5) . . ? C50 C45 C32 120.0(5) . . ? C47 C46 C45 118.7(5) . . ? C47 C46 C51 120.4(5) . . ? C45 C46 C51 120.9(5) . . ? C48 C47 C46 121.2(6) . . ? C48 C47 H45 119.4 . . ? C46 C47 H45 119.4 . . ? C49 C48 C47 120.9(6) . . ? C49 C48 H46 119.5 . . ? C47 C48 H46 119.5 . . ? C48 C49 C50 120.5(6) . . ? C48 C49 H47 119.8 . . ? C50 C49 H47 119.8 . . ? C45 C50 C49 118.7(5) . . ? C45 C50 C52 120.5(5) . . ? C49 C50 C52 120.8(5) . . ? C46 C51 H48 109.5 . . ? C46 C51 H49 109.5 . . ? H48 C51 H49 109.5 . . ? C46 C51 H50 109.5 . . ? H48 C51 H50 109.5 . . ? H49 C51 H50 109.5 . . ? C50 C52 H51 109.5 . . ? C50 C52 H52 109.5 . . ? H51 C52 H52 109.5 . . ? C50 C52 H53 109.5 . . ? H51 C52 H53 109.5 . . ? H52 C52 H53 109.5 . . ? C58 C53 C54 121.2(5) . . ? C58 C53 C34 119.3(5) . . ? C54 C53 C34 119.5(6) . . ? C53 C54 C55 117.1(7) . . ? C53 C54 C59 121.3(5) . . ? C55 C54 C59 121.5(6) . . ? C56 C55 C54 122.0(6) . . ? C56 C55 H54 119.0 . . ? C54 C55 H54 119.0 . . ? C55 C56 C57 119.5(6) . . ? C55 C56 H55 120.3 . . ? C57 C56 H55 120.3 . . ? C56 C57 C58 121.6(7) . . ? C56 C57 H56 119.2 . . ? C58 C57 H56 119.2 . . ? C57 C58 C53 118.5(6) . . ? C57 C58 C60 119.7(6) . . ? C53 C58 C60 121.7(5) . . ? C54 C59 H57 109.5 . . ? C54 C59 H58 109.5 . . ? H57 C59 H58 109.5 . . ? C54 C59 H59 109.5 . . ? H57 C59 H59 109.5 . . ? H58 C59 H59 109.5 . . ? C58 C60 H60 109.5 . . ? C58 C60 H61 109.5 . . ? H60 C60 H61 109.5 . . ? C58 C60 H62 109.5 . . ? H60 C60 H62 109.5 . . ? H61 C60 H62 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 C5 N1 C1 C2 -0.5(6) . . . . ? C6 N1 C1 C2 178.0(4) . . . . ? C5 N1 C1 S1 -178.6(4) . . . . ? C6 N1 C1 S1 -0.1(6) . . . . ? N1 C1 C2 C3 -0.2(6) . . . . ? S1 C1 C2 C3 177.9(4) . . . . ? N1 C1 C2 C15 177.0(4) . . . . ? S1 C1 C2 C15 -4.9(6) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C15 C2 C3 C4 -177.9(4) . . . . ? C2 C3 C4 C5 2.1(7) . . . . ? C2 C3 C4 C23 -177.5(5) . . . . ? C3 C4 C5 N1 -2.7(7) . . . . ? C23 C4 C5 N1 176.8(4) . . . . ? C1 N1 C5 C4 2.0(7) . . . . ? C6 N1 C5 C4 -176.5(5) . . . . ? C5 N1 C6 C7 86.1(6) . . . . ? C1 N1 C6 C7 -92.5(5) . . . . ? C5 N1 C6 C11 -91.0(5) . . . . ? C1 N1 C6 C11 90.4(6) . . . . ? C11 C6 C7 C8 0.9(8) . . . . ? N1 C6 C7 C8 -176.1(5) . . . . ? C11 C6 C7 C12 -178.4(5) . . . . ? N1 C6 C7 C12 4.5(7) . . . . ? C6 C7 C8 C9 -2.0(8) . . . . ? C12 C7 C8 C9 177.3(5) . . . . ? C7 C8 C9 C10 2.5(8) . . . . ? C7 C8 C9 C13 179.1(6) . . . . ? C8 C9 C10 C11 -1.8(8) . . . . ? C13 C9 C10 C11 -178.2(6) . . . . ? C7 C6 C11 C10 -0.3(7) . . . . ? N1 C6 C11 C10 176.8(4) . . . . ? C7 C6 C11 C14 178.8(5) . . . . ? N1 C6 C11 C14 -4.2(7) . . . . ? C9 C10 C11 C6 0.7(8) . . . . ? C9 C10 C11 C14 -178.3(5) . . . . ? C3 C2 C15 C20 -91.3(6) . . . . ? C1 C2 C15 C20 91.3(6) . . . . ? C3 C2 C15 C16 86.4(6) . . . . ? C1 C2 C15 C16 -90.9(6) . . . . ? C20 C15 C16 C17 0.9(8) . . . . ? C2 C15 C16 C17 -176.8(5) . . . . ? C20 C15 C16 C21 179.7(5) . . . . ? C2 C15 C16 C21 2.0(7) . . . . ? C15 C16 C17 C18 -1.0(8) . . . . ? C21 C16 C17 C18 -179.9(5) . . . . ? C16 C17 C18 C19 1.1(9) . . . . ? C17 C18 C19 C20 -1.0(9) . . . . ? C18 C19 C20 C15 0.9(9) . . . . ? C18 C19 C20 C22 -178.7(6) . . . . ? C16 C15 C20 C19 -0.8(8) . . . . ? C2 C15 C20 C19 176.9(5) . . . . ? C16 C15 C20 C22 178.8(5) . . . . ? C2 C15 C20 C22 -3.5(8) . . . . ? C5 C4 C23 C24 94.0(7) . . . . ? C3 C4 C23 C24 -86.5(6) . . . . ? C5 C4 C23 C28 -89.9(6) . . . . ? C3 C4 C23 C28 89.7(6) . . . . ? C28 C23 C24 C25 0.7(8) . . . . ? C4 C23 C24 C25 176.7(5) . . . . ? C28 C23 C24 C29 -179.3(5) . . . . ? C4 C23 C24 C29 -3.2(8) . . . . ? C23 C24 C25 C26 -0.8(9) . . . . ? C29 C24 C25 C26 179.2(6) . . . . ? C24 C25 C26 C27 1.3(10) . . . . ? C25 C26 C27 C28 -1.6(10) . . . . ? C26 C27 C28 C23 1.5(9) . . . . ? C26 C27 C28 C30 -176.2(6) . . . . ? C24 C23 C28 C27 -1.0(8) . . . . ? C4 C23 C28 C27 -177.1(5) . . . . ? C24 C23 C28 C30 176.6(5) . . . . ? C4 C23 C28 C30 0.5(8) . . . . ? C35 N2 C31 C32 -0.3(7) . . . . ? C36 N2 C31 C32 -179.6(4) . . . . ? C35 N2 C31 S2 -179.9(4) . . . . ? C36 N2 C31 S2 0.9(7) . . . . ? N2 C31 C32 C33 -0.6(7) . . . . ? S2 C31 C32 C33 178.9(4) . . . . ? N2 C31 C32 C45 178.7(4) . . . . ? S2 C31 C32 C45 -1.8(7) . . . . ? C31 C32 C33 C34 0.5(8) . . . . ? C45 C32 C33 C34 -178.8(5) . . . . ? C32 C33 C34 C35 0.6(8) . . . . ? C32 C33 C34 C53 179.1(5) . . . . ? C33 C34 C35 N2 -1.5(8) . . . . ? C53 C34 C35 N2 180.0(5) . . . . ? C31 N2 C35 C34 1.5(8) . . . . ? C36 N2 C35 C34 -179.2(5) . . . . ? C31 N2 C36 C41 -95.6(6) . . . . ? C35 N2 C36 C41 85.1(6) . . . . ? C31 N2 C36 C37 86.8(6) . . . . ? C35 N2 C36 C37 -92.5(5) . . . . ? C41 C36 C37 C38 -0.5(7) . . . . ? N2 C36 C37 C38 176.9(4) . . . . ? C41 C36 C37 C42 179.2(5) . . . . ? N2 C36 C37 C42 -3.4(7) . . . . ? C36 C37 C38 C39 0.0(8) . . . . ? C42 C37 C38 C39 -179.7(5) . . . . ? C37 C38 C39 C40 1.2(9) . . . . ? C37 C38 C39 C43 178.5(6) . . . . ? C38 C39 C40 C41 -2.0(9) . . . . ? C43 C39 C40 C41 -179.2(6) . . . . ? C37 C36 C41 C40 -0.2(8) . . . . ? N2 C36 C41 C40 -177.7(4) . . . . ? C37 C36 C41 C44 179.8(5) . . . . ? N2 C36 C41 C44 2.4(7) . . . . ? C39 C40 C41 C36 1.5(9) . . . . ? C39 C40 C41 C44 -178.5(6) . . . . ? C33 C32 C45 C46 -98.9(6) . . . . ? C31 C32 C45 C46 81.8(6) . . . . ? C33 C32 C45 C50 78.5(6) . . . . ? C31 C32 C45 C50 -100.9(6) . . . . ? C50 C45 C46 C47 -0.2(8) . . . . ? C32 C45 C46 C47 177.2(5) . . . . ? C50 C45 C46 C51 179.4(5) . . . . ? C32 C45 C46 C51 -3.2(8) . . . . ? C45 C46 C47 C48 -0.3(8) . . . . ? C51 C46 C47 C48 -179.9(6) . . . . ? C46 C47 C48 C49 0.0(9) . . . . ? C47 C48 C49 C50 0.8(9) . . . . ? C46 C45 C50 C49 0.9(8) . . . . ? C32 C45 C50 C49 -176.4(5) . . . . ? C46 C45 C50 C52 -178.0(5) . . . . ? C32 C45 C50 C52 4.6(8) . . . . ? C48 C49 C50 C45 -1.2(8) . . . . ? C48 C49 C50 C52 177.7(5) . . . . ? C35 C34 C53 C58 111.9(6) . . . . ? C33 C34 C53 C58 -66.5(7) . . . . ? C35 C34 C53 C54 -66.6(7) . . . . ? C33 C34 C53 C54 114.9(6) . . . . ? C58 C53 C54 C55 2.4(8) . . . . ? C34 C53 C54 C55 -179.1(5) . . . . ? C58 C53 C54 C59 -179.9(5) . . . . ? C34 C53 C54 C59 -1.4(8) . . . . ? C53 C54 C55 C56 -0.9(9) . . . . ? C59 C54 C55 C56 -178.6(6) . . . . ? C54 C55 C56 C57 0.1(10) . . . . ? C55 C56 C57 C58 -0.9(10) . . . . ? C56 C57 C58 C53 2.3(9) . . . . ? C56 C57 C58 C60 -177.3(6) . . . . ? C54 C53 C58 C57 -3.1(8) . . . . ? C34 C53 C58 C57 178.4(5) . . . . ? C54 C53 C58 C60 176.5(5) . . . . ? C34 C53 C58 C60 -2.0(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.902 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.069 data_compound6 _database_code_depnum_ccdc_archive 'CCDC 879862' #TrackingRef 'compound6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H39 Au Cl N' _chemical_formula_weight 730.11 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.666(3) _cell_length_b 16.763(3) _cell_length_c 15.097(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.758(3) _cell_angle_gamma 90.00 _cell_volume 3212.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123.1500 _cell_measurement_reflns_used 8250 _cell_measurement_theta_min 3.0061 _cell_measurement_theta_max 27.7257 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 4.688 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4540 _exptl_absorpt_correction_T_max 0.8721 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20932 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5639 _reflns_number_gt 5022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0606P)^2^+114.2284P] 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 5639 _refine_ls_number_parameters 369 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0905 _refine_ls_R_factor_gt 0.0845 _refine_ls_wR_factor_ref 0.2359 _refine_ls_wR_factor_gt 0.2331 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.196 _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 Au1 Au -0.13909(5) 0.16521(4) 0.32987(5) 0.0413(2) Uani 1 1 d . . . Cl1 Cl -0.2769(4) 0.1598(3) 0.3837(4) 0.0556(11) Uani 1 1 d . . . C1 C -0.0171(13) 0.1672(9) 0.2858(10) 0.036(3) Uani 1 1 d . . . N1 N 0.0267(10) 0.0981(8) 0.2677(9) 0.036(3) Uani 1 1 d . . . C2 C 0.1094(10) 0.0980(9) 0.2366(9) 0.028(3) Uani 1 1 d . . . H1 H 0.1387 0.0486 0.2278 0.034 Uiso 1 1 calc R . . C3 C 0.1504(10) 0.1678(8) 0.2182(9) 0.025(3) Uani 1 1 d . . . C4 C 0.1078(11) 0.2387(9) 0.2352(10) 0.032(3) Uani 1 1 d . . . H2 H 0.1360 0.2882 0.2252 0.038 Uiso 1 1 calc R . . C5 C 0.0248(10) 0.2377(8) 0.2665(9) 0.029(3) Uani 1 1 d D . . C6 C -0.0132(11) 0.0218(9) 0.2854(10) 0.033(3) Uani 1 1 d . . . C7 C 0.0360(11) -0.0149(10) 0.3757(10) 0.037(3) Uani 1 1 d . . . C8 C -0.0017(12) -0.0868(11) 0.3893(12) 0.043(4) Uani 1 1 d . . . H3 H 0.0290 -0.1115 0.4500 0.051 Uiso 1 1 calc R . . C9 C -0.0820(13) -0.1253(11) 0.3193(13) 0.047(4) Uani 1 1 d . . . C10 C -0.1304(13) -0.0885(12) 0.2305(12) 0.048(4) Uani 1 1 d . . . H4 H -0.1869 -0.1145 0.1820 0.058 Uiso 1 1 calc R . . C11 C -0.0967(13) -0.0145(12) 0.2131(11) 0.048(4) Uani 1 1 d . . . C12 C 0.1263(12) 0.0255(11) 0.4528(11) 0.044(4) Uani 1 1 d . . . H5 H 0.1359 0.0015 0.5146 0.066 Uiso 1 1 calc R . . H6 H 0.1109 0.0825 0.4542 0.066 Uiso 1 1 calc R . . H7 H 0.1909 0.0188 0.4397 0.066 Uiso 1 1 calc R . . C13 C -0.135(2) -0.1958(14) 0.326(2) 0.094(9) Uani 1 1 d . . . H8 H -0.0937 -0.2421 0.3211 0.141 Uiso 1 1 calc R . . H9 H -0.2042 -0.1972 0.2734 0.141 Uiso 1 1 calc R . . H10 H -0.1448 -0.1969 0.3868 0.141 Uiso 1 1 calc R . . C14 C -0.1451(18) 0.0259(14) 0.1187(14) 0.070(6) Uani 1 1 d . . . H11 H -0.1698 0.0790 0.1277 0.105 Uiso 1 1 calc R . . H12 H -0.2049 -0.0058 0.0773 0.105 Uiso 1 1 calc R . . H13 H -0.0926 0.0308 0.0891 0.105 Uiso 1 1 calc R . . C15 C 0.2405(11) 0.1674(8) 0.1830(10) 0.030(3) Uani 1 1 d . . . C16 C 0.2184(12) 0.1704(10) 0.0851(11) 0.039(4) Uani 1 1 d . . . C17 C 0.2992(13) 0.1693(10) 0.0550(13) 0.045(4) Uani 1 1 d . . . H14 H 0.2845 0.1723 -0.0115 0.054 Uiso 1 1 calc R . . C18 C 0.4046(14) 0.1638(11) 0.1178(14) 0.051(4) Uani 1 1 d . . . H15 H 0.4604 0.1615 0.0947 0.061 Uiso 1 1 calc R . . C19 C 0.4242(12) 0.1621(9) 0.2136(13) 0.042(4) Uani 1 1 d . . . H16 H 0.4953 0.1593 0.2569 0.051 Uiso 1 1 calc R . . C20 C 0.3453(12) 0.1644(8) 0.2505(11) 0.035(3) Uani 1 1 d . . . C21 C 0.1060(14) 0.1758(15) 0.0137(13) 0.064(6) Uani 1 1 d . . . H17 H 0.1064 0.1810 -0.0508 0.097 Uiso 1 1 calc R . . H18 H 0.0714 0.2224 0.0283 0.097 Uiso 1 1 calc R . . H19 H 0.0675 0.1274 0.0175 0.097 Uiso 1 1 calc R . . C22 C 0.3670(13) 0.1629(11) 0.3543(12) 0.048(4) Uani 1 1 d . . . H20 H 0.4433 0.1630 0.3898 0.071 Uiso 1 1 calc R . . H21 H 0.3363 0.1146 0.3700 0.071 Uiso 1 1 calc R . . H22 H 0.3358 0.2101 0.3717 0.071 Uiso 1 1 calc R . . C23 C -0.0165(10) 0.3171(9) 0.2814(12) 0.040(4) Uani 1 1 d D . . C24 C 0.0221(12) 0.3518(11) 0.3709(13) 0.055(5) Uani 1 1 d D . . C25 C -0.0186(14) 0.4247(12) 0.3808(16) 0.066(6) Uani 1 1 d D . . H23 H 0.0064 0.4497 0.4416 0.079 Uiso 1 1 calc R . . C26 C -0.0933(14) 0.4624(11) 0.3065(18) 0.070(6) Uani 1 1 d D . . H24 H -0.1197 0.5129 0.3159 0.084 Uiso 1 1 calc R . . C27 C -0.1305(13) 0.4276(12) 0.2184(17) 0.065(6) Uani 1 1 d D . . H25 H -0.1822 0.4545 0.1668 0.078 Uiso 1 1 calc R . . C28 C -0.0942(12) 0.3542(11) 0.2032(13) 0.050(4) Uani 1 1 d DU . . C29 C 0.1066(15) 0.3072(15) 0.4522(14) 0.084(8) Uani 1 1 d D . . H26 H 0.0821 0.2530 0.4568 0.126 Uiso 1 1 calc R . . H27 H 0.1201 0.3355 0.5124 0.126 Uiso 1 1 calc R . . H28 H 0.1718 0.3047 0.4393 0.126 Uiso 1 1 calc R . . C30 C -0.1360(14) 0.3170(12) 0.1060(14) 0.066(5) Uani 1 1 d DU . . H29 H -0.1468 0.3584 0.0575 0.100 Uiso 1 1 calc R . . H30 H -0.2032 0.2906 0.0961 0.100 Uiso 1 1 calc R . . H31 H -0.0853 0.2777 0.1009 0.100 Uiso 1 1 calc R . . C31 C 0.1893(16) 0.4238(12) 0.1648(15) 0.062(5) Uani 1 1 d . . . C32 C 0.2823(15) 0.3833(10) 0.1853(16) 0.050(5) Uani 1 1 d . . . H32 H 0.2999 0.3621 0.1347 0.060 Uiso 1 1 calc R . . C33 C 0.3456(16) 0.3736(11) 0.272(2) 0.069(7) Uani 1 1 d . . . H33 H 0.4082 0.3438 0.2828 0.082 Uiso 1 1 calc R . . C34 C 0.3273(15) 0.4057(12) 0.3534(16) 0.060(5) Uani 1 1 d . . . H34 H 0.3761 0.3985 0.4168 0.072 Uiso 1 1 calc R . . C35 C 0.2366(16) 0.4463(12) 0.3334(15) 0.060(5) Uani 1 1 d . . . H35 H 0.2207 0.4683 0.3845 0.073 Uiso 1 1 calc R . . C36 C 0.1653(13) 0.4570(9) 0.2403(14) 0.046(4) Uani 1 1 d . . . H36 H 0.1019 0.4861 0.2278 0.055 Uiso 1 1 calc R . . C37 C 0.115(2) 0.4300(16) 0.0673(17) 0.089(8) Uani 1 1 d . . . H37 H 0.1400 0.4693 0.0327 0.134 Uiso 1 1 calc R . . H38 H 0.0460 0.4469 0.0673 0.134 Uiso 1 1 calc R . . H39 H 0.1074 0.3779 0.0359 0.134 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 Au1 0.0424(4) 0.0428(4) 0.0421(4) 0.0031(3) 0.0196(3) 0.0040(3) Cl1 0.047(2) 0.066(3) 0.065(3) -0.005(2) 0.033(2) 0.006(2) C1 0.045(9) 0.036(8) 0.028(7) 0.002(6) 0.013(7) 0.002(7) N1 0.037(7) 0.040(7) 0.029(6) 0.004(5) 0.011(5) 0.004(6) C2 0.022(7) 0.034(8) 0.028(7) -0.003(6) 0.008(6) 0.000(6) C3 0.020(6) 0.026(7) 0.029(7) 0.000(5) 0.008(5) 0.003(5) C4 0.029(7) 0.030(7) 0.035(8) -0.002(6) 0.010(6) -0.001(6) C5 0.026(7) 0.036(8) 0.023(7) -0.004(6) 0.008(6) 0.004(6) C6 0.030(7) 0.036(8) 0.036(8) -0.004(6) 0.017(6) 0.006(6) C7 0.028(7) 0.052(10) 0.034(8) -0.001(7) 0.017(6) 0.009(7) C8 0.029(8) 0.065(11) 0.041(9) 0.010(8) 0.021(7) 0.007(7) C9 0.033(8) 0.057(11) 0.065(11) 0.001(9) 0.033(8) 0.003(8) C10 0.038(9) 0.069(12) 0.040(9) -0.001(8) 0.016(8) -0.002(8) C11 0.035(8) 0.072(12) 0.034(8) -0.005(8) 0.008(7) 0.004(8) C12 0.031(8) 0.058(11) 0.040(9) 0.002(8) 0.010(7) 0.012(7) C13 0.12(2) 0.069(14) 0.13(2) -0.071(16) 0.090(19) -0.049(15) C14 0.074(14) 0.074(14) 0.046(11) 0.006(10) 0.003(10) -0.018(11) C15 0.027(7) 0.021(6) 0.039(8) -0.007(6) 0.011(6) -0.002(5) C16 0.031(8) 0.044(9) 0.040(8) -0.005(7) 0.011(7) -0.006(7) C17 0.045(9) 0.046(10) 0.045(9) -0.010(8) 0.017(8) -0.002(7) C18 0.044(10) 0.062(11) 0.063(11) -0.007(9) 0.038(9) -0.010(8) C19 0.029(8) 0.036(8) 0.058(10) 0.002(7) 0.011(7) -0.003(6) C20 0.031(8) 0.022(7) 0.048(9) 0.004(6) 0.010(7) -0.002(6) C21 0.032(9) 0.115(18) 0.039(10) -0.001(10) 0.004(8) 0.004(10) C22 0.040(9) 0.056(11) 0.041(9) 0.001(8) 0.007(8) 0.010(8) C23 0.033(8) 0.043(9) 0.050(9) -0.007(7) 0.023(7) -0.004(7) C24 0.050(10) 0.073(13) 0.051(10) -0.013(9) 0.029(9) -0.005(9) C25 0.054(12) 0.082(15) 0.074(14) -0.030(12) 0.038(11) 0.000(11) C26 0.042(10) 0.058(12) 0.119(19) -0.015(12) 0.042(12) 0.025(9) C27 0.030(9) 0.078(14) 0.090(16) -0.004(12) 0.026(10) 0.011(9) C28 0.040(7) 0.056(7) 0.055(7) -0.001(6) 0.018(6) 0.001(6) C29 0.073(15) 0.14(2) 0.042(11) -0.012(13) 0.031(11) 0.023(15) C30 0.056(8) 0.065(8) 0.063(8) -0.001(7) 0.004(6) 0.002(7) C31 0.064(13) 0.049(11) 0.066(13) -0.002(9) 0.017(10) -0.035(10) C32 0.048(11) 0.031(9) 0.086(14) -0.009(9) 0.043(11) -0.007(8) C33 0.047(11) 0.033(10) 0.13(2) 0.011(12) 0.040(14) -0.001(8) C34 0.046(11) 0.058(12) 0.071(13) 0.021(10) 0.017(10) 0.000(9) C35 0.061(13) 0.057(12) 0.068(13) -0.013(10) 0.030(11) -0.022(10) C36 0.033(8) 0.025(8) 0.082(13) -0.001(8) 0.026(9) -0.005(6) C37 0.10(2) 0.089(18) 0.069(15) -0.011(13) 0.024(14) -0.024(15) _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 Au1 C1 2.011(16) . ? Au1 Cl1 2.314(4) . ? C1 N1 1.377(19) . ? C1 C5 1.39(2) . ? N1 C2 1.375(18) . ? N1 C6 1.454(19) . ? C2 C3 1.369(19) . ? C2 H1 0.9500 . ? C3 C4 1.389(19) . ? C3 C15 1.511(19) . ? C4 C5 1.381(18) . ? C4 H2 0.9500 . ? C5 C23 1.49(2) . ? C6 C11 1.39(2) . ? C6 C7 1.42(2) . ? C7 C8 1.36(2) . ? C7 C12 1.51(2) . ? C8 C9 1.37(2) . ? C8 H3 0.9500 . ? C9 C10 1.40(2) . ? C9 C13 1.41(3) . ? C10 C11 1.38(3) . ? C10 H4 0.9500 . ? C11 C14 1.49(2) . ? C12 H5 0.9800 . ? C12 H6 0.9800 . ? C12 H7 0.9800 . ? C13 H8 0.9800 . ? C13 H9 0.9800 . ? C13 H10 0.9800 . ? C14 H11 0.9800 . ? C14 H12 0.9800 . ? C14 H13 0.9800 . ? C15 C16 1.40(2) . ? C15 C20 1.42(2) . ? C16 C17 1.34(2) . ? C16 C21 1.52(2) . ? C17 C18 1.40(2) . ? C17 H14 0.9500 . ? C18 C19 1.37(2) . ? C18 H15 0.9500 . ? C19 C20 1.39(2) . ? C19 H16 0.9500 . ? C20 C22 1.48(2) . ? C21 H17 0.9800 . ? C21 H18 0.9800 . ? C21 H19 0.9800 . ? C22 H20 0.9800 . ? C22 H21 0.9800 . ? C22 H22 0.9800 . ? C23 C24 1.38(2) . ? C23 C28 1.41(2) . ? C24 C25 1.37(3) . ? C24 C29 1.53(3) . ? C25 C26 1.36(3) . ? C25 H23 0.9500 . ? C26 C27 1.37(3) . ? C26 H24 0.9500 . ? C27 C28 1.38(3) . ? C27 H25 0.9500 . ? C28 C30 1.50(3) . ? C29 H26 0.9800 . ? C29 H27 0.9800 . ? C29 H28 0.9800 . ? C30 H29 0.9800 . ? C30 H30 0.9800 . ? C30 H31 0.9800 . ? C31 C32 1.37(3) . ? C31 C36 1.41(3) . ? C31 C37 1.45(3) . ? C32 C33 1.28(3) . ? C32 H32 0.9500 . ? C33 C34 1.45(3) . ? C33 H33 0.9500 . ? C34 C35 1.35(3) . ? C34 H34 0.9500 . ? C35 C36 1.39(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37 0.9800 . ? C37 H38 0.9800 . ? C37 H39 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 C1 Au1 Cl1 178.3(4) . . ? N1 C1 C5 115.4(13) . . ? N1 C1 Au1 121.8(11) . . ? C5 C1 Au1 122.7(11) . . ? C2 N1 C1 122.9(13) . . ? C2 N1 C6 118.2(12) . . ? C1 N1 C6 118.9(12) . . ? C3 C2 N1 121.2(13) . . ? C3 C2 H1 119.4 . . ? N1 C2 H1 119.4 . . ? C2 C3 C4 117.6(12) . . ? C2 C3 C15 121.0(12) . . ? C4 C3 C15 121.3(12) . . ? C5 C4 C3 120.4(13) . . ? C5 C4 H2 119.8 . . ? C3 C4 H2 119.8 . . ? C4 C5 C1 122.5(13) . . ? C4 C5 C23 116.4(9) . . ? C1 C5 C23 121.1(9) . . ? C11 C6 C7 121.5(15) . . ? C11 C6 N1 119.6(14) . . ? C7 C6 N1 118.8(13) . . ? C8 C7 C6 117.4(14) . . ? C8 C7 C12 122.0(14) . . ? C6 C7 C12 120.5(15) . . ? C7 C8 C9 122.9(16) . . ? C7 C8 H3 118.6 . . ? C9 C8 H3 118.6 . . ? C8 C9 C10 119.3(17) . . ? C8 C9 C13 129(2) . . ? C10 C9 C13 111(2) . . ? C11 C10 C9 120.4(17) . . ? C11 C10 H4 119.8 . . ? C9 C10 H4 119.8 . . ? C10 C11 C6 118.5(16) . . ? C10 C11 C14 121.8(16) . . ? C6 C11 C14 119.7(17) . . ? C7 C12 H5 109.5 . . ? C7 C12 H6 109.5 . . ? H5 C12 H6 109.5 . . ? C7 C12 H7 109.5 . . ? H5 C12 H7 109.5 . . ? H6 C12 H7 109.5 . . ? C9 C13 H8 109.5 . . ? C9 C13 H9 109.5 . . ? H8 C13 H9 109.5 . . ? C9 C13 H10 109.5 . . ? H8 C13 H10 109.5 . . ? H9 C13 H10 109.5 . . ? C11 C14 H11 109.5 . . ? C11 C14 H12 109.5 . . ? H11 C14 H12 109.5 . . ? C11 C14 H13 109.5 . . ? H11 C14 H13 109.5 . . ? H12 C14 H13 109.5 . . ? C16 C15 C20 121.8(14) . . ? C16 C15 C3 119.2(12) . . ? C20 C15 C3 119.1(13) . . ? C17 C16 C15 118.4(15) . . ? C17 C16 C21 120.3(16) . . ? C15 C16 C21 121.2(14) . . ? C16 C17 C18 122.7(16) . . ? C16 C17 H14 118.6 . . ? C18 C17 H14 118.6 . . ? C19 C18 C17 117.6(15) . . ? C19 C18 H15 121.2 . . ? C17 C18 H15 121.2 . . ? C18 C19 C20 123.2(15) . . ? C18 C19 H16 118.4 . . ? C20 C19 H16 118.4 . . ? C19 C20 C15 116.2(15) . . ? C19 C20 C22 122.9(14) . . ? C15 C20 C22 120.9(14) . . ? C16 C21 H17 109.5 . . ? C16 C21 H18 109.5 . . ? H17 C21 H18 109.5 . . ? C16 C21 H19 109.5 . . ? H17 C21 H19 109.5 . . ? H18 C21 H19 109.5 . . ? C20 C22 H20 109.5 . . ? C20 C22 H21 109.5 . . ? H20 C22 H21 109.5 . . ? C20 C22 H22 109.5 . . ? H20 C22 H22 109.5 . . ? H21 C22 H22 109.5 . . ? C24 C23 C28 121.9(16) . . ? C24 C23 C5 119.6(16) . . ? C28 C23 C5 118.5(15) . . ? C25 C24 C23 117.2(19) . . ? C25 C24 C29 124.3(19) . . ? C23 C24 C29 118.5(18) . . ? C26 C25 C24 122(2) . . ? C26 C25 H23 118.8 . . ? C24 C25 H23 118.8 . . ? C25 C26 C27 119.9(17) . . ? C25 C26 H24 120.1 . . ? C27 C26 H24 120.1 . . ? C26 C27 C28 121.2(19) . . ? C26 C27 H25 119.4 . . ? C28 C27 H25 119.4 . . ? C27 C28 C23 117.5(18) . . ? C27 C28 C30 120.3(18) . . ? C23 C28 C30 122.1(17) . . ? C24 C29 H26 109.5 . . ? C24 C29 H27 109.5 . . ? H26 C29 H27 109.5 . . ? C24 C29 H28 109.5 . . ? H26 C29 H28 109.5 . . ? H27 C29 H28 109.5 . . ? C28 C30 H29 109.5 . . ? C28 C30 H30 109.5 . . ? H29 C30 H30 109.5 . . ? C28 C30 H31 109.5 . . ? H29 C30 H31 109.5 . . ? H30 C30 H31 109.5 . . ? C32 C31 C36 119.2(19) . . ? C32 C31 C37 121(2) . . ? C36 C31 C37 120(2) . . ? C33 C32 C31 121(2) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C34 123.7(19) . . ? C32 C33 H33 118.2 . . ? C34 C33 H33 118.2 . . ? C35 C34 C33 116(2) . . ? C35 C34 H34 122.2 . . ? C33 C34 H34 122.2 . . ? C34 C35 C36 122(2) . . ? C34 C35 H35 118.9 . . ? C36 C35 H35 118.9 . . ? C35 C36 C31 118.6(17) . . ? C35 C36 H36 120.7 . . ? C31 C36 H36 120.7 . . ? C31 C37 H37 109.5 . . ? C31 C37 H38 109.5 . . ? H37 C37 H38 109.5 . . ? C31 C37 H39 109.5 . . ? H37 C37 H39 109.5 . . ? H38 C37 H39 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 C5 C1 N1 C2 3(2) . . . . ? Au1 C1 N1 C2 179.3(10) . . . . ? C5 C1 N1 C6 -179.6(13) . . . . ? Au1 C1 N1 C6 -3.0(18) . . . . ? C1 N1 C2 C3 -3(2) . . . . ? C6 N1 C2 C3 179.7(13) . . . . ? N1 C2 C3 C4 2(2) . . . . ? N1 C2 C3 C15 -179.3(12) . . . . ? C2 C3 C4 C5 -2(2) . . . . ? C15 C3 C4 C5 179.4(13) . . . . ? C3 C4 C5 C1 3(2) . . . . ? C3 C4 C5 C23 -179.1(13) . . . . ? N1 C1 C5 C4 -3(2) . . . . ? Au1 C1 C5 C4 -179.2(11) . . . . ? N1 C1 C5 C23 179.0(13) . . . . ? Au1 C1 C5 C23 2.5(19) . . . . ? C2 N1 C6 C11 -92.8(16) . . . . ? C1 N1 C6 C11 89.5(17) . . . . ? C2 N1 C6 C7 85.7(16) . . . . ? C1 N1 C6 C7 -92.0(16) . . . . ? C11 C6 C7 C8 0(2) . . . . ? N1 C6 C7 C8 -178.7(13) . . . . ? C11 C6 C7 C12 180.0(14) . . . . ? N1 C6 C7 C12 1.5(19) . . . . ? C6 C7 C8 C9 2(2) . . . . ? C12 C7 C8 C9 -178.4(14) . . . . ? C7 C8 C9 C10 -2(2) . . . . ? C7 C8 C9 C13 -173.5(18) . . . . ? C8 C9 C10 C11 1(2) . . . . ? C13 C9 C10 C11 173.7(17) . . . . ? C9 C10 C11 C6 1(2) . . . . ? C9 C10 C11 C14 178.8(18) . . . . ? C7 C6 C11 C10 -1(2) . . . . ? N1 C6 C11 C10 177.5(14) . . . . ? C7 C6 C11 C14 -179.2(16) . . . . ? N1 C6 C11 C14 -1(2) . . . . ? C2 C3 C15 C16 93.9(17) . . . . ? C4 C3 C15 C16 -87.7(17) . . . . ? C2 C3 C15 C20 -86.4(16) . . . . ? C4 C3 C15 C20 91.9(16) . . . . ? C20 C15 C16 C17 1(2) . . . . ? C3 C15 C16 C17 -179.4(13) . . . . ? C20 C15 C16 C21 -178.3(16) . . . . ? C3 C15 C16 C21 1(2) . . . . ? C15 C16 C17 C18 1(3) . . . . ? C21 C16 C17 C18 -179.6(18) . . . . ? C16 C17 C18 C19 -2(3) . . . . ? C17 C18 C19 C20 1(3) . . . . ? C18 C19 C20 C15 1(2) . . . . ? C18 C19 C20 C22 -179.7(16) . . . . ? C16 C15 C20 C19 -2(2) . . . . ? C3 C15 C20 C19 178.4(12) . . . . ? C16 C15 C20 C22 178.8(14) . . . . ? C3 C15 C20 C22 -1(2) . . . . ? C4 C5 C23 C24 -93.4(12) . . . . ? C1 C5 C23 C24 84.9(13) . . . . ? C4 C5 C23 C28 86.8(12) . . . . ? C1 C5 C23 C28 -94.8(14) . . . . ? C28 C23 C24 C25 -0.2(7) . . . . ? C5 C23 C24 C25 -180.0(5) . . . . ? C28 C23 C24 C29 179.9(7) . . . . ? C5 C23 C24 C29 0.1(5) . . . . ? C23 C24 C25 C26 -0.2(11) . . . . ? C29 C24 C25 C26 179.7(8) . . . . ? C24 C25 C26 C27 0.0(15) . . . . ? C25 C26 C27 C28 0.6(16) . . . . ? C26 C27 C28 C23 -0.9(14) . . . . ? C26 C27 C28 C30 180.0(9) . . . . ? C24 C23 C28 C27 0.7(10) . . . . ? C5 C23 C28 C27 -179.5(7) . . . . ? C24 C23 C28 C30 179.8(6) . . . . ? C5 C23 C28 C30 -0.4(10) . . . . ? C36 C31 C32 C33 2(3) . . . . ? C37 C31 C32 C33 -175.9(19) . . . . ? C31 C32 C33 C34 -2(3) . . . . ? C32 C33 C34 C35 1(3) . . . . ? C33 C34 C35 C36 0(3) . . . . ? C34 C35 C36 C31 0(3) . . . . ? C32 C31 C36 C35 -1(2) . . . . ? C37 C31 C36 C35 176.7(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 3.562 _refine_diff_density_min -4.143 _refine_diff_density_rms 0.236 data_compound7 _database_code_depnum_ccdc_archive 'CCDC 879863' #TrackingRef 'compound7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H41 N' _chemical_formula_weight 463.68 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' _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 9.355(4) _cell_length_b 13.050(5) _cell_length_c 13.097(4) _cell_angle_alpha 62.601(11) _cell_angle_beta 79.653(16) _cell_angle_gamma 89.316(18) _cell_volume 1391.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3713 _cell_measurement_theta_min 3.0357 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.106 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type None _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9281 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4791 _reflns_number_gt 3390 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0805P)^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 4791 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1361 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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 0.73843(16) 0.22870(12) 0.24562(12) 0.0237(3) Uani 1 1 d . . . C1 C 0.66721(18) 0.32954(14) 0.20135(14) 0.0218(4) Uani 1 1 d . . . H1 H 0.6191 0.3442 0.1385 0.026 Uiso 1 1 calc R . . C2 C 0.66185(18) 0.40711(14) 0.24106(14) 0.0196(4) Uani 1 1 d . . . C3 C 0.74712(18) 0.39574(14) 0.33523(14) 0.0208(4) Uani 1 1 d . . . H2 H 0.6776 0.4083 0.3952 0.025 Uiso 1 1 calc R . . C4 C 0.78912(18) 0.26952(14) 0.39801(14) 0.0214(4) Uani 1 1 d . . . C5 C 0.78505(19) 0.19951(15) 0.34926(14) 0.0237(4) Uani 1 1 d . . . H3 H 0.8166 0.1241 0.3888 0.028 Uiso 1 1 calc R . . C6 C 0.72441(19) 0.14640(14) 0.20319(14) 0.0229(4) Uani 1 1 d . . . C7 C 0.84356(19) 0.13447(14) 0.12989(14) 0.0242(4) Uani 1 1 d . . . C8 C 0.8252(2) 0.05962(15) 0.08351(14) 0.0265(4) Uani 1 1 d . . . H4 H 0.9060 0.0498 0.0343 0.032 Uiso 1 1 calc R . . C9 C 0.6923(2) -0.00108(14) 0.10692(15) 0.0274(4) Uani 1 1 d . . . C10 C 0.5765(2) 0.01294(15) 0.18059(15) 0.0288(4) Uani 1 1 d . . . H5 H 0.4851 -0.0281 0.1973 0.035 Uiso 1 1 calc R . . C11 C 0.5894(2) 0.08506(14) 0.23099(14) 0.0254(4) Uani 1 1 d . . . C12 C 0.9874(2) 0.20063(17) 0.10171(17) 0.0352(5) Uani 1 1 d . . . H6 H 1.0334 0.1674 0.1705 0.053 Uiso 1 1 calc R . . H7 H 0.9719 0.2819 0.0801 0.053 Uiso 1 1 calc R . . H8 H 1.0509 0.1959 0.0360 0.053 Uiso 1 1 calc R . . C13 C 0.6753(2) -0.08196(17) 0.05598(18) 0.0403(5) Uani 1 1 d . . . H9 H 0.7059 -0.1580 0.1063 0.060 Uiso 1 1 calc R . . H10 H 0.7361 -0.0505 -0.0228 0.060 Uiso 1 1 calc R . . H11 H 0.5730 -0.0899 0.0513 0.060 Uiso 1 1 calc R . . C14 C 0.4612(2) 0.09528(17) 0.31308(16) 0.0364(5) Uani 1 1 d . . . H12 H 0.4191 0.1690 0.2722 0.055 Uiso 1 1 calc R . . H13 H 0.4939 0.0924 0.3813 0.055 Uiso 1 1 calc R . . H14 H 0.3875 0.0311 0.3391 0.055 Uiso 1 1 calc R . . C15 C 0.56525(18) 0.50367(14) 0.19094(14) 0.0211(4) Uani 1 1 d . . . C16 C 0.59510(19) 0.58387(14) 0.06990(15) 0.0228(4) Uani 1 1 d . . . C17 C 0.5076(2) 0.67570(15) 0.02749(16) 0.0274(4) Uani 1 1 d . . . H15 H 0.5311 0.7320 -0.0527 0.033 Uiso 1 1 calc R . . C18 C 0.3876(2) 0.68683(15) 0.09926(16) 0.0309(5) Uani 1 1 d . . . H16 H 0.3295 0.7502 0.0689 0.037 Uiso 1 1 calc R . . C19 C 0.3533(2) 0.60450(15) 0.21577(16) 0.0288(4) Uani 1 1 d . . . H17 H 0.2688 0.6102 0.2648 0.035 Uiso 1 1 calc R . . C20 C 0.44041(19) 0.51318(15) 0.26257(15) 0.0242(4) Uani 1 1 d . . . C21 C 0.7168(2) 0.57573(16) -0.01825(15) 0.0292(4) Uani 1 1 d . . . H18 H 0.6845 0.5216 -0.0437 0.044 Uiso 1 1 calc R . . H19 H 0.8019 0.5479 0.0179 0.044 Uiso 1 1 calc R . . H20 H 0.7431 0.6524 -0.0862 0.044 Uiso 1 1 calc R . . C22 C 0.3927(2) 0.42448(16) 0.38973(15) 0.0324(5) Uani 1 1 d . . . H21 H 0.4371 0.4476 0.4391 0.049 Uiso 1 1 calc R . . H22 H 0.4237 0.3487 0.4005 0.049 Uiso 1 1 calc R . . H23 H 0.2863 0.4196 0.4121 0.049 Uiso 1 1 calc R . . C23 C 0.83697(19) 0.21986(14) 0.51363(14) 0.0242(4) Uani 1 1 d . . . C24 C 0.7460(2) 0.21662(14) 0.61371(15) 0.0248(4) Uani 1 1 d . . . C25 C 0.7927(2) 0.16982(15) 0.72039(15) 0.0312(5) Uani 1 1 d . . . H24 H 0.7310 0.1686 0.7871 0.037 Uiso 1 1 calc R . . C26 C 0.9267(2) 0.12529(16) 0.73081(16) 0.0361(5) Uani 1 1 d . . . H25 H 0.9576 0.0945 0.8038 0.043 Uiso 1 1 calc R . . C27 C 1.0156(2) 0.12572(17) 0.63434(17) 0.0359(5) Uani 1 1 d . . . H26 H 1.1073 0.0940 0.6421 0.043 Uiso 1 1 calc R . . C28 C 0.9738(2) 0.17175(15) 0.52560(16) 0.0293(4) Uani 1 1 d . . . C29 C 0.5965(2) 0.26071(16) 0.61041(15) 0.0297(4) Uani 1 1 d . . . H27 H 0.5384 0.2269 0.6902 0.044 Uiso 1 1 calc R . . H28 H 0.5485 0.2387 0.5619 0.044 Uiso 1 1 calc R . . H29 H 0.6053 0.3453 0.5769 0.044 Uiso 1 1 calc R . . C30 C 1.0814(2) 0.16954(18) 0.42567(17) 0.0394(5) Uani 1 1 d . . . H30 H 1.1805 0.1698 0.4403 0.059 Uiso 1 1 calc R . . H31 H 1.0741 0.2380 0.3521 0.059 Uiso 1 1 calc R . . H32 H 1.0592 0.0994 0.4198 0.059 Uiso 1 1 calc R . . C31 C 0.87904(19) 0.48960(15) 0.28851(14) 0.0239(4) Uani 1 1 d . . . C32 C 0.9948(2) 0.47853(17) 0.19644(16) 0.0316(5) Uani 1 1 d . . . H33 H 1.0736 0.5397 0.1674 0.047 Uiso 1 1 calc R . . H34 H 0.9507 0.4860 0.1311 0.047 Uiso 1 1 calc R . . H35 H 1.0342 0.4027 0.2318 0.047 Uiso 1 1 calc R . . C33 C 0.8247(2) 0.61156(15) 0.23571(16) 0.0303(4) Uani 1 1 d . . . H36 H 0.7452 0.6166 0.2928 0.045 Uiso 1 1 calc R . . H37 H 0.7893 0.6268 0.1644 0.045 Uiso 1 1 calc R . . H38 H 0.9050 0.6690 0.2163 0.045 Uiso 1 1 calc R . . C34 C 0.9468(2) 0.47784(16) 0.39119(15) 0.0304(4) Uani 1 1 d . . . H39 H 0.9975 0.4067 0.4201 0.046 Uiso 1 1 calc R . . H40 H 0.8699 0.4746 0.4544 0.046 Uiso 1 1 calc R . . H41 H 1.0165 0.5447 0.3647 0.046 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 0.0331(9) 0.0208(8) 0.0240(8) -0.0140(7) -0.0114(7) 0.0073(6) C1 0.0250(9) 0.0207(9) 0.0214(9) -0.0099(8) -0.0083(7) 0.0032(7) C2 0.0206(9) 0.0186(9) 0.0196(8) -0.0089(7) -0.0038(7) 0.0015(7) C3 0.0229(9) 0.0212(9) 0.0203(8) -0.0113(7) -0.0048(7) 0.0047(7) C4 0.0208(9) 0.0221(9) 0.0213(9) -0.0103(8) -0.0040(7) 0.0042(7) C5 0.0276(10) 0.0204(9) 0.0233(9) -0.0099(8) -0.0070(8) 0.0065(7) C6 0.0316(10) 0.0181(9) 0.0215(9) -0.0107(8) -0.0075(8) 0.0061(7) C7 0.0312(10) 0.0191(9) 0.0229(9) -0.0092(8) -0.0090(8) 0.0074(8) C8 0.0331(11) 0.0243(10) 0.0246(9) -0.0132(8) -0.0073(8) 0.0119(8) C9 0.0411(11) 0.0176(9) 0.0285(10) -0.0120(8) -0.0153(9) 0.0089(8) C10 0.0342(11) 0.0203(9) 0.0320(10) -0.0116(8) -0.0081(8) -0.0007(8) C11 0.0314(10) 0.0204(9) 0.0220(9) -0.0082(8) -0.0043(8) 0.0026(8) C12 0.0312(11) 0.0377(11) 0.0390(11) -0.0212(10) -0.0027(9) 0.0019(9) C13 0.0578(14) 0.0320(11) 0.0430(12) -0.0253(10) -0.0163(11) 0.0085(10) C14 0.0342(11) 0.0372(12) 0.0359(11) -0.0188(10) 0.0028(9) -0.0012(9) C15 0.0241(9) 0.0173(9) 0.0268(9) -0.0127(8) -0.0098(7) 0.0015(7) C16 0.0263(10) 0.0209(9) 0.0271(9) -0.0142(8) -0.0107(8) 0.0013(7) C17 0.0367(11) 0.0220(9) 0.0284(10) -0.0126(8) -0.0157(8) 0.0023(8) C18 0.0370(11) 0.0264(10) 0.0397(11) -0.0200(9) -0.0205(9) 0.0125(8) C19 0.0252(10) 0.0332(11) 0.0378(11) -0.0229(9) -0.0113(8) 0.0082(8) C20 0.0242(9) 0.0248(10) 0.0291(9) -0.0158(8) -0.0092(8) 0.0026(7) C21 0.0344(11) 0.0266(10) 0.0244(9) -0.0098(8) -0.0067(8) -0.0009(8) C22 0.0264(10) 0.0364(11) 0.0328(10) -0.0158(9) -0.0028(8) 0.0058(8) C23 0.0308(10) 0.0208(9) 0.0247(9) -0.0128(8) -0.0085(8) 0.0050(8) C24 0.0340(10) 0.0175(9) 0.0235(9) -0.0097(8) -0.0065(8) 0.0036(8) C25 0.0449(12) 0.0265(10) 0.0247(10) -0.0132(8) -0.0090(9) 0.0071(9) C26 0.0519(13) 0.0356(11) 0.0271(10) -0.0155(9) -0.0210(9) 0.0143(10) C27 0.0405(12) 0.0367(11) 0.0371(11) -0.0186(10) -0.0197(9) 0.0165(9) C28 0.0342(11) 0.0270(10) 0.0309(10) -0.0156(9) -0.0110(8) 0.0090(8) C29 0.0358(11) 0.0278(10) 0.0218(9) -0.0099(8) -0.0018(8) 0.0040(8) C30 0.0371(12) 0.0502(13) 0.0400(11) -0.0269(10) -0.0138(9) 0.0184(10) C31 0.0253(9) 0.0250(9) 0.0232(9) -0.0123(8) -0.0056(7) -0.0005(8) C32 0.0272(10) 0.0371(11) 0.0307(10) -0.0173(9) -0.0012(8) -0.0033(9) C33 0.0366(11) 0.0245(10) 0.0312(10) -0.0135(8) -0.0082(8) -0.0044(8) C34 0.0320(10) 0.0314(11) 0.0313(10) -0.0167(9) -0.0086(8) -0.0025(8) _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 C5 1.382(2) . ? N1 C1 1.388(2) . ? N1 C6 1.435(2) . ? C1 C2 1.331(2) . ? C1 H1 0.9500 . ? C2 C15 1.503(2) . ? C2 C3 1.537(2) . ? C3 C4 1.549(2) . ? C3 C31 1.573(2) . ? C3 H2 1.0000 . ? C4 C5 1.338(2) . ? C4 C23 1.499(2) . ? C5 H3 0.9500 . ? C6 C7 1.392(2) . ? C6 C11 1.400(3) . ? C7 C8 1.393(2) . ? C7 C12 1.499(3) . ? C8 C9 1.389(3) . ? C8 H4 0.9500 . ? C9 C10 1.386(3) . ? C9 C13 1.508(3) . ? C10 C11 1.393(2) . ? C10 H5 0.9500 . ? C11 C14 1.509(3) . ? C12 H6 0.9800 . ? C12 H7 0.9800 . ? C12 H8 0.9800 . ? C13 H9 0.9800 . ? C13 H10 0.9800 . ? C13 H11 0.9800 . ? C14 H12 0.9800 . ? C14 H13 0.9800 . ? C14 H14 0.9800 . ? C15 C20 1.403(2) . ? C15 C16 1.417(2) . ? C16 C17 1.393(2) . ? C16 C21 1.509(2) . ? C17 C18 1.381(3) . ? C17 H15 0.9500 . ? C18 C19 1.382(3) . ? C18 H16 0.9500 . ? C19 C20 1.395(2) . ? C19 H17 0.9500 . ? C20 C22 1.511(2) . ? C21 H18 0.9800 . ? C21 H19 0.9800 . ? C21 H20 0.9800 . ? C22 H21 0.9800 . ? C22 H22 0.9800 . ? C22 H23 0.9800 . ? C23 C24 1.412(2) . ? C23 C28 1.422(2) . ? C24 C25 1.394(2) . ? C24 C29 1.507(2) . ? C25 C26 1.378(3) . ? C25 H24 0.9500 . ? C26 C27 1.380(3) . ? C26 H25 0.9500 . ? C27 C28 1.396(3) . ? C27 H26 0.9500 . ? C28 C30 1.512(3) . ? C29 H27 0.9800 . ? C29 H28 0.9800 . ? C29 H29 0.9800 . ? C30 H30 0.9800 . ? C30 H31 0.9800 . ? C30 H32 0.9800 . ? C31 C32 1.528(2) . ? C31 C34 1.532(2) . ? C31 C33 1.537(2) . ? C32 H33 0.9800 . ? C32 H34 0.9800 . ? C32 H35 0.9800 . ? C33 H36 0.9800 . ? C33 H37 0.9800 . ? C33 H38 0.9800 . ? C34 H39 0.9800 . ? C34 H40 0.9800 . ? C34 H41 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 C5 N1 C1 116.40(14) . . ? C5 N1 C6 122.18(14) . . ? C1 N1 C6 119.05(13) . . ? C2 C1 N1 124.36(15) . . ? C2 C1 H1 117.8 . . ? N1 C1 H1 117.8 . . ? C1 C2 C15 116.25(15) . . ? C1 C2 C3 121.33(15) . . ? C15 C2 C3 122.40(14) . . ? C2 C3 C4 108.86(13) . . ? C2 C3 C31 113.93(13) . . ? C4 C3 C31 113.93(14) . . ? C2 C3 H2 106.5 . . ? C4 C3 H2 106.5 . . ? C31 C3 H2 106.5 . . ? C5 C4 C23 116.81(15) . . ? C5 C4 C3 120.42(15) . . ? C23 C4 C3 122.78(14) . . ? C4 C5 N1 124.89(16) . . ? C4 C5 H3 117.6 . . ? N1 C5 H3 117.6 . . ? C7 C6 C11 121.66(16) . . ? C7 C6 N1 118.94(16) . . ? C11 C6 N1 119.30(15) . . ? C6 C7 C8 118.12(16) . . ? C6 C7 C12 120.77(16) . . ? C8 C7 C12 121.11(16) . . ? C9 C8 C7 122.07(17) . . ? C9 C8 H4 119.0 . . ? C7 C8 H4 119.0 . . ? C10 C9 C8 118.00(16) . . ? C10 C9 C13 120.94(18) . . ? C8 C9 C13 121.04(18) . . ? C9 C10 C11 122.36(17) . . ? C9 C10 H5 118.8 . . ? C11 C10 H5 118.8 . . ? C10 C11 C6 117.76(17) . . ? C10 C11 C14 120.45(17) . . ? C6 C11 C14 121.78(16) . . ? C7 C12 H6 109.5 . . ? C7 C12 H7 109.5 . . ? H6 C12 H7 109.5 . . ? C7 C12 H8 109.5 . . ? H6 C12 H8 109.5 . . ? H7 C12 H8 109.5 . . ? C9 C13 H9 109.5 . . ? C9 C13 H10 109.5 . . ? H9 C13 H10 109.5 . . ? C9 C13 H11 109.5 . . ? H9 C13 H11 109.5 . . ? H10 C13 H11 109.5 . . ? C11 C14 H12 109.5 . . ? C11 C14 H13 109.5 . . ? H12 C14 H13 109.5 . . ? C11 C14 H14 109.5 . . ? H12 C14 H14 109.5 . . ? H13 C14 H14 109.5 . . ? C20 C15 C16 118.76(15) . . ? C20 C15 C2 120.45(14) . . ? C16 C15 C2 120.75(15) . . ? C17 C16 C15 119.21(16) . . ? C17 C16 C21 116.97(15) . . ? C15 C16 C21 123.82(15) . . ? C18 C17 C16 121.59(16) . . ? C18 C17 H15 119.2 . . ? C16 C17 H15 119.2 . . ? C17 C18 C19 119.11(16) . . ? C17 C18 H16 120.4 . . ? C19 C18 H16 120.4 . . ? C18 C19 C20 121.11(17) . . ? C18 C19 H17 119.4 . . ? C20 C19 H17 119.4 . . ? C19 C20 C15 119.98(16) . . ? C19 C20 C22 117.90(16) . . ? C15 C20 C22 122.08(15) . . ? C16 C21 H18 109.5 . . ? C16 C21 H19 109.5 . . ? H18 C21 H19 109.5 . . ? C16 C21 H20 109.5 . . ? H18 C21 H20 109.5 . . ? H19 C21 H20 109.5 . . ? C20 C22 H21 109.5 . . ? C20 C22 H22 109.5 . . ? H21 C22 H22 109.5 . . ? C20 C22 H23 109.5 . . ? H21 C22 H23 109.5 . . ? H22 C22 H23 109.5 . . ? C24 C23 C28 118.44(15) . . ? C24 C23 C4 121.05(16) . . ? C28 C23 C4 120.48(15) . . ? C25 C24 C23 120.06(17) . . ? C25 C24 C29 117.87(16) . . ? C23 C24 C29 122.07(15) . . ? C26 C25 C24 121.16(18) . . ? C26 C25 H24 119.4 . . ? C24 C25 H24 119.4 . . ? C25 C26 C27 119.47(17) . . ? C25 C26 H25 120.3 . . ? C27 C26 H25 120.3 . . ? C26 C27 C28 121.51(18) . . ? C26 C27 H26 119.2 . . ? C28 C27 H26 119.2 . . ? C27 C28 C23 119.34(17) . . ? C27 C28 C30 116.82(17) . . ? C23 C28 C30 123.82(15) . . ? C24 C29 H27 109.5 . . ? C24 C29 H28 109.5 . . ? H27 C29 H28 109.5 . . ? C24 C29 H29 109.5 . . ? H27 C29 H29 109.5 . . ? H28 C29 H29 109.5 . . ? C28 C30 H30 109.5 . . ? C28 C30 H31 109.5 . . ? H30 C30 H31 109.5 . . ? C28 C30 H32 109.5 . . ? H30 C30 H32 109.5 . . ? H31 C30 H32 109.5 . . ? C32 C31 C34 109.87(15) . . ? C32 C31 C33 109.56(14) . . ? C34 C31 C33 106.05(15) . . ? C32 C31 C3 111.63(14) . . ? C34 C31 C3 109.60(14) . . ? C33 C31 C3 109.97(14) . . ? C31 C32 H33 109.5 . . ? C31 C32 H34 109.5 . . ? H33 C32 H34 109.5 . . ? C31 C32 H35 109.5 . . ? H33 C32 H35 109.5 . . ? H34 C32 H35 109.5 . . ? C31 C33 H36 109.5 . . ? C31 C33 H37 109.5 . . ? H36 C33 H37 109.5 . . ? C31 C33 H38 109.5 . . ? H36 C33 H38 109.5 . . ? H37 C33 H38 109.5 . . ? C31 C34 H39 109.5 . . ? C31 C34 H40 109.5 . . ? H39 C34 H40 109.5 . . ? C31 C34 H41 109.5 . . ? H39 C34 H41 109.5 . . ? H40 C34 H41 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 C5 N1 C1 C2 11.0(2) . . . . ? C6 N1 C1 C2 173.94(16) . . . . ? N1 C1 C2 C15 -173.29(15) . . . . ? N1 C1 C2 C3 5.2(3) . . . . ? C1 C2 C3 C4 -18.3(2) . . . . ? C15 C2 C3 C4 160.10(14) . . . . ? C1 C2 C3 C31 110.10(18) . . . . ? C15 C2 C3 C31 -71.5(2) . . . . ? C2 C3 C4 C5 17.3(2) . . . . ? C31 C3 C4 C5 -111.11(18) . . . . ? C2 C3 C4 C23 -163.33(15) . . . . ? C31 C3 C4 C23 68.3(2) . . . . ? C23 C4 C5 N1 177.34(16) . . . . ? C3 C4 C5 N1 -3.2(3) . . . . ? C1 N1 C5 C4 -12.0(3) . . . . ? C6 N1 C5 C4 -174.34(16) . . . . ? C5 N1 C6 C7 -90.0(2) . . . . ? C1 N1 C6 C7 108.10(18) . . . . ? C5 N1 C6 C11 93.6(2) . . . . ? C1 N1 C6 C11 -68.3(2) . . . . ? C11 C6 C7 C8 0.4(2) . . . . ? N1 C6 C7 C8 -175.95(14) . . . . ? C11 C6 C7 C12 -179.73(16) . . . . ? N1 C6 C7 C12 3.9(2) . . . . ? C6 C7 C8 C9 1.0(2) . . . . ? C12 C7 C8 C9 -178.93(16) . . . . ? C7 C8 C9 C10 -1.2(2) . . . . ? C7 C8 C9 C13 -179.77(16) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C13 C9 C10 C11 178.64(16) . . . . ? C9 C10 C11 C6 1.2(3) . . . . ? C9 C10 C11 C14 -178.48(15) . . . . ? C7 C6 C11 C10 -1.4(2) . . . . ? N1 C6 C11 C10 174.88(14) . . . . ? C7 C6 C11 C14 178.27(15) . . . . ? N1 C6 C11 C14 -5.4(2) . . . . ? C1 C2 C15 C20 114.04(18) . . . . ? C3 C2 C15 C20 -64.4(2) . . . . ? C1 C2 C15 C16 -63.4(2) . . . . ? C3 C2 C15 C16 118.13(17) . . . . ? C20 C15 C16 C17 5.7(2) . . . . ? C2 C15 C16 C17 -176.78(15) . . . . ? C20 C15 C16 C21 -173.65(16) . . . . ? C2 C15 C16 C21 3.9(2) . . . . ? C15 C16 C17 C18 -3.7(2) . . . . ? C21 C16 C17 C18 175.72(16) . . . . ? C16 C17 C18 C19 -0.3(3) . . . . ? C17 C18 C19 C20 2.3(3) . . . . ? C18 C19 C20 C15 -0.1(3) . . . . ? C18 C19 C20 C22 -177.99(17) . . . . ? C16 C15 C20 C19 -3.9(2) . . . . ? C2 C15 C20 C19 178.63(15) . . . . ? C16 C15 C20 C22 173.89(16) . . . . ? C2 C15 C20 C22 -3.6(2) . . . . ? C5 C4 C23 C24 -122.09(19) . . . . ? C3 C4 C23 C24 58.5(2) . . . . ? C5 C4 C23 C28 56.1(2) . . . . ? C3 C4 C23 C28 -123.38(18) . . . . ? C28 C23 C24 C25 1.7(3) . . . . ? C4 C23 C24 C25 179.87(16) . . . . ? C28 C23 C24 C29 -177.23(16) . . . . ? C4 C23 C24 C29 1.0(3) . . . . ? C23 C24 C25 C26 -0.5(3) . . . . ? C29 C24 C25 C26 178.45(17) . . . . ? C24 C25 C26 C27 -0.8(3) . . . . ? C25 C26 C27 C28 0.9(3) . . . . ? C26 C27 C28 C23 0.3(3) . . . . ? C26 C27 C28 C30 178.87(19) . . . . ? C24 C23 C28 C27 -1.6(3) . . . . ? C4 C23 C28 C27 -179.79(17) . . . . ? C24 C23 C28 C30 179.98(18) . . . . ? C4 C23 C28 C30 1.8(3) . . . . ? C2 C3 C31 C32 -63.54(18) . . . . ? C4 C3 C31 C32 62.19(18) . . . . ? C2 C3 C31 C34 174.50(14) . . . . ? C4 C3 C31 C34 -59.77(19) . . . . ? C2 C3 C31 C33 58.28(19) . . . . ? C4 C3 C31 C33 -175.99(14) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.192 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.042 data_compound9 _database_code_depnum_ccdc_archive 'CCDC 879864' #TrackingRef 'compound9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H29 N' _chemical_formula_weight 403.54 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.727(3) _cell_length_b 12.934(3) _cell_length_c 15.910(4) _cell_angle_alpha 98.919(2) _cell_angle_beta 105.428(5) _cell_angle_gamma 93.867(4) _cell_volume 2283.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4872 _cell_measurement_theta_min 3.0845 _cell_measurement_theta_max 27.5259 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type None _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 CCD (4x4 bin mode) with MicroMax-007 ; _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15506 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.1065 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7886 _reflns_number_gt 4568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0813P)^2^+0.0742P] 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 7886 _refine_ls_number_parameters 571 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1384 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.1913 _refine_ls_wR_factor_gt 0.1595 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.4551(2) -0.0913(2) 0.28040(17) 0.0222(6) Uani 1 1 d . . . C1 C 0.3834(3) -0.0149(3) 0.3045(2) 0.0228(8) Uani 1 1 d . . . C2 C 0.2715(3) -0.0648(3) 0.2903(2) 0.0321(9) Uani 1 1 d . . . H1 H 0.2051 -0.0325 0.3009 0.039 Uiso 1 1 calc R . . C3 C 0.2717(3) -0.1748(3) 0.2563(2) 0.0306(9) Uani 1 1 d . . . C4 C 0.3880(3) -0.1897(3) 0.2506(2) 0.0206(7) Uani 1 1 d . . . C5 C 0.1819(3) -0.2580(3) 0.2313(2) 0.0345(9) Uani 1 1 d . . . H2 H 0.1039 -0.2477 0.2352 0.041 Uiso 1 1 calc R . . C6 C 0.2095(3) -0.3579(3) 0.2000(3) 0.0387(10) Uani 1 1 d . . . C7 C 0.3241(3) -0.3703(3) 0.1944(2) 0.0350(9) Uani 1 1 d . . . H3 H 0.3404 -0.4391 0.1736 0.042 Uiso 1 1 calc R . . C8 C 0.4169(3) -0.2890(3) 0.2172(2) 0.0316(9) Uani 1 1 d . . . C9 C 0.5746(3) -0.0642(3) 0.2903(2) 0.0239(8) Uani 1 1 d . . . H4 H 0.6212 -0.1163 0.2729 0.029 Uiso 1 1 calc R . . C10 C 0.6262(3) 0.0366(3) 0.3247(2) 0.0215(8) Uani 1 1 d . . . C11 C 0.5544(3) 0.1146(3) 0.3483(2) 0.0235(8) Uani 1 1 d . . . H5 H 0.5901 0.1849 0.3717 0.028 Uiso 1 1 calc R . . C12 C 0.4351(3) 0.0907(3) 0.3380(2) 0.0218(8) Uani 1 1 d . . . C13 C 0.1148(4) -0.4529(3) 0.1711(3) 0.0572(13) Uani 1 1 d . . . H6 H 0.0401 -0.4315 0.1808 0.086 Uiso 1 1 calc R . . H7 H 0.1413 -0.5075 0.2059 0.086 Uiso 1 1 calc R . . H8 H 0.1023 -0.4807 0.1080 0.086 Uiso 1 1 calc R . . C14 C 0.5345(3) -0.3115(3) 0.2058(3) 0.0377(10) Uani 1 1 d . . . H9 H 0.5298 -0.3854 0.1781 0.057 Uiso 1 1 calc R . . H10 H 0.5939 -0.2983 0.2639 0.057 Uiso 1 1 calc R . . H11 H 0.5576 -0.2658 0.1680 0.057 Uiso 1 1 calc R . . C15 C 0.7563(3) 0.0641(3) 0.3364(2) 0.0210(8) Uani 1 1 d . . . C16 C 0.8372(3) 0.0783(3) 0.4204(2) 0.0240(8) Uani 1 1 d . . . C17 C 0.9585(3) 0.1020(3) 0.4288(2) 0.0269(8) Uani 1 1 d . . . H12 H 1.0146 0.1101 0.4854 0.032 Uiso 1 1 calc R . . C18 C 0.9979(3) 0.1138(3) 0.3560(2) 0.0295(9) Uani 1 1 d . . . H13 H 1.0805 0.1297 0.3627 0.035 Uiso 1 1 calc R . . C19 C 0.9170(3) 0.1024(3) 0.2738(2) 0.0276(8) Uani 1 1 d . . . H14 H 0.9445 0.1128 0.2243 0.033 Uiso 1 1 calc R . . C20 C 0.7953(3) 0.0759(3) 0.2613(2) 0.0234(8) Uani 1 1 d . . . C21 C 0.7973(3) 0.0662(3) 0.5015(2) 0.0335(9) Uani 1 1 d . . . H15 H 0.7376 0.1142 0.5075 0.050 Uiso 1 1 calc R . . H16 H 0.8659 0.0830 0.5543 0.050 Uiso 1 1 calc R . . H17 H 0.7624 -0.0066 0.4954 0.050 Uiso 1 1 calc R . . C22 C 0.7099(3) 0.0558(3) 0.1698(2) 0.0323(9) Uani 1 1 d . . . H18 H 0.7458 0.0887 0.1300 0.048 Uiso 1 1 calc R . . H19 H 0.6360 0.0860 0.1719 0.048 Uiso 1 1 calc R . . H20 H 0.6923 -0.0202 0.1478 0.048 Uiso 1 1 calc R . . C23 C 0.3613(3) 0.1735(3) 0.3630(2) 0.0238(8) Uani 1 1 d . . . C24 C 0.3719(3) 0.2093(3) 0.4533(2) 0.0267(8) Uani 1 1 d . . . C25 C 0.3071(3) 0.2907(3) 0.4755(3) 0.0352(10) Uani 1 1 d . . . H21 H 0.3127 0.3152 0.5361 0.042 Uiso 1 1 calc R . . C26 C 0.2349(3) 0.3365(3) 0.4114(3) 0.0392(10) Uani 1 1 d . . . H22 H 0.1932 0.3932 0.4277 0.047 Uiso 1 1 calc R . . C27 C 0.2241(3) 0.2989(3) 0.3235(3) 0.0367(10) Uani 1 1 d . . . H23 H 0.1732 0.3295 0.2794 0.044 Uiso 1 1 calc R . . C28 C 0.2853(3) 0.2179(3) 0.2977(2) 0.0288(8) Uani 1 1 d . . . C29 C 0.4524(3) 0.1633(3) 0.5241(2) 0.0344(9) Uani 1 1 d . . . H24 H 0.5354 0.1818 0.5256 0.052 Uiso 1 1 calc R . . H25 H 0.4340 0.0865 0.5116 0.052 Uiso 1 1 calc R . . H26 H 0.4405 0.1914 0.5817 0.052 Uiso 1 1 calc R . . C30 C 0.2714(4) 0.1788(4) 0.2004(2) 0.0465(11) Uani 1 1 d . . . H27 H 0.3497 0.1681 0.1916 0.070 Uiso 1 1 calc R . . H28 H 0.2362 0.2310 0.1658 0.070 Uiso 1 1 calc R . . H29 H 0.2195 0.1119 0.1807 0.070 Uiso 1 1 calc R . . N2 N 0.7879(2) 0.5560(2) 0.21102(18) 0.0231(7) Uani 1 1 d . . . C31 C 0.7591(3) 0.4743(3) 0.1360(2) 0.0241(8) Uani 1 1 d . . . C32 C 0.7688(3) 0.5159(3) 0.0637(2) 0.0307(9) Uani 1 1 d . . . H30 H 0.7539 0.4780 0.0050 0.037 Uiso 1 1 calc R . . C33 C 0.8053(3) 0.6259(3) 0.0922(2) 0.0271(8) Uani 1 1 d . . . C34 C 0.8176(3) 0.6505(3) 0.1848(2) 0.0224(8) Uani 1 1 d . . . C35 C 0.8307(3) 0.7054(3) 0.0473(2) 0.0297(9) Uani 1 1 d . . . H31 H 0.8228 0.6897 -0.0145 0.036 Uiso 1 1 calc R . . C36 C 0.8671(3) 0.8064(3) 0.0934(2) 0.0320(9) Uani 1 1 d . . . C37 C 0.8780(3) 0.8281(3) 0.1847(2) 0.0290(9) Uani 1 1 d . . . H32 H 0.9028 0.8987 0.2150 0.035 Uiso 1 1 calc R . . C38 C 0.8550(3) 0.7532(3) 0.2332(2) 0.0234(8) Uani 1 1 d . . . C39 C 0.7803(3) 0.5373(3) 0.2928(2) 0.0237(8) Uani 1 1 d . . . H33 H 0.7983 0.5938 0.3418 0.028 Uiso 1 1 calc R . . C40 C 0.7472(3) 0.4386(3) 0.3033(2) 0.0249(8) Uani 1 1 d . . . C41 C 0.7239(3) 0.3537(3) 0.2291(2) 0.0282(8) Uani 1 1 d . . . H34 H 0.7043 0.2841 0.2371 0.034 Uiso 1 1 calc R . . C42 C 0.7290(3) 0.3695(3) 0.1479(2) 0.0252(8) Uani 1 1 d . . . C43 C 0.8929(4) 0.8965(3) 0.0478(3) 0.0426(10) Uani 1 1 d . . . H35 H 0.9093 0.8681 -0.0081 0.064 Uiso 1 1 calc R . . H36 H 0.9624 0.9434 0.0864 0.064 Uiso 1 1 calc R . . H37 H 0.8238 0.9361 0.0356 0.064 Uiso 1 1 calc R . . C44 C 0.8747(3) 0.7847(3) 0.3319(2) 0.0330(9) Uani 1 1 d . . . H38 H 0.9041 0.8598 0.3503 0.050 Uiso 1 1 calc R . . H39 H 0.9333 0.7432 0.3632 0.050 Uiso 1 1 calc R . . H40 H 0.7993 0.7716 0.3462 0.050 Uiso 1 1 calc R . . C45 C 0.7341(3) 0.4178(3) 0.3907(2) 0.0234(8) Uani 1 1 d . . . C46 C 0.6237(3) 0.4236(3) 0.4081(2) 0.0277(8) Uani 1 1 d . . . C47 C 0.6127(3) 0.4021(3) 0.4887(3) 0.0325(9) Uani 1 1 d . . . H41 H 0.5386 0.4070 0.5019 0.039 Uiso 1 1 calc R . . C48 C 0.7067(4) 0.3738(3) 0.5497(3) 0.0363(10) Uani 1 1 d . . . H42 H 0.6972 0.3592 0.6044 0.044 Uiso 1 1 calc R . . C49 C 0.8157(3) 0.3665(3) 0.5315(2) 0.0346(9) Uani 1 1 d . . . H43 H 0.8805 0.3466 0.5737 0.042 Uiso 1 1 calc R . . C50 C 0.8305(3) 0.3883(3) 0.4521(2) 0.0299(9) Uani 1 1 d . . . C51 C 0.5186(3) 0.4525(3) 0.3415(3) 0.0395(10) Uani 1 1 d . . . H44 H 0.5324 0.5269 0.3374 0.059 Uiso 1 1 calc R . . H45 H 0.4466 0.4408 0.3605 0.059 Uiso 1 1 calc R . . H46 H 0.5085 0.4086 0.2834 0.059 Uiso 1 1 calc R . . C52 C 0.9481(3) 0.3783(3) 0.4312(2) 0.0364(10) Uani 1 1 d . . . H47 H 1.0054 0.3581 0.4814 0.055 Uiso 1 1 calc R . . H48 H 0.9786 0.4460 0.4204 0.055 Uiso 1 1 calc R . . H49 H 0.9367 0.3243 0.3783 0.055 Uiso 1 1 calc R . . C53 C 0.7045(3) 0.2813(3) 0.0708(2) 0.0294(9) Uani 1 1 d . . . C54 C 0.5889(3) 0.2325(3) 0.0307(2) 0.0377(10) Uani 1 1 d . . . C55 C 0.5713(4) 0.1432(3) -0.0355(3) 0.0480(11) Uani 1 1 d . . . H50 H 0.4936 0.1071 -0.0617 0.058 Uiso 1 1 calc R . . C56 C 0.6661(5) 0.1071(3) -0.0629(3) 0.0509(12) Uani 1 1 d . . . H51 H 0.6530 0.0471 -0.1086 0.061 Uiso 1 1 calc R . . C57 C 0.7771(4) 0.1566(3) -0.0253(3) 0.0435(11) Uani 1 1 d . . . H52 H 0.8413 0.1310 -0.0451 0.052 Uiso 1 1 calc R . . C58 C 0.7997(4) 0.2438(3) 0.0416(2) 0.0359(10) Uani 1 1 d . . . C59 C 0.4843(4) 0.2737(4) 0.0591(3) 0.0651(14) Uani 1 1 d . . . H53 H 0.4912 0.2640 0.1200 0.098 Uiso 1 1 calc R . . H54 H 0.4099 0.2349 0.0195 0.098 Uiso 1 1 calc R . . H55 H 0.4844 0.3488 0.0560 0.098 Uiso 1 1 calc R . . C60 C 0.9255(4) 0.2945(3) 0.0842(3) 0.0535(13) Uani 1 1 d . . . H56 H 0.9809 0.2484 0.0661 0.080 Uiso 1 1 calc R . . H57 H 0.9417 0.3057 0.1488 0.080 Uiso 1 1 calc R . . H58 H 0.9357 0.3624 0.0655 0.080 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 0.0247(16) 0.0181(16) 0.0218(16) 0.0017(12) 0.0045(12) 0.0004(13) C1 0.0236(19) 0.027(2) 0.0199(18) 0.0081(16) 0.0067(15) 0.0055(16) C2 0.030(2) 0.035(2) 0.034(2) 0.0097(18) 0.0113(18) 0.0118(18) C3 0.028(2) 0.032(2) 0.032(2) 0.0115(18) 0.0070(17) 0.0009(17) C4 0.0194(18) 0.0161(18) 0.0245(19) 0.0004(15) 0.0050(15) 0.0013(14) C5 0.0180(19) 0.045(3) 0.038(2) 0.013(2) 0.0019(16) -0.0037(18) C6 0.036(2) 0.035(2) 0.042(2) 0.011(2) 0.0050(19) -0.0009(19) C7 0.040(2) 0.023(2) 0.031(2) 0.0084(17) -0.0063(17) -0.0119(17) C8 0.033(2) 0.034(2) 0.027(2) 0.0081(17) 0.0046(17) 0.0065(18) C9 0.0193(18) 0.025(2) 0.029(2) 0.0078(16) 0.0084(15) 0.0004(15) C10 0.0248(18) 0.0197(19) 0.0190(18) 0.0051(15) 0.0041(15) 0.0008(15) C11 0.0256(19) 0.0220(19) 0.0225(19) 0.0016(15) 0.0085(15) -0.0008(15) C12 0.0277(19) 0.0199(19) 0.0170(18) 0.0045(15) 0.0044(15) 0.0033(15) C13 0.032(2) 0.043(3) 0.091(4) 0.012(3) 0.011(2) -0.005(2) C14 0.036(2) 0.032(2) 0.042(2) 0.0025(19) 0.0076(19) 0.0098(19) C15 0.0221(18) 0.0154(18) 0.0245(19) 0.0015(15) 0.0060(15) 0.0022(14) C16 0.027(2) 0.0179(19) 0.028(2) 0.0031(15) 0.0088(16) 0.0040(15) C17 0.0243(19) 0.023(2) 0.029(2) -0.0022(16) 0.0043(16) 0.0003(15) C18 0.028(2) 0.023(2) 0.039(2) 0.0031(17) 0.0159(18) -0.0002(16) C19 0.032(2) 0.021(2) 0.035(2) 0.0022(17) 0.0196(18) 0.0009(16) C20 0.033(2) 0.0128(18) 0.028(2) 0.0037(15) 0.0138(17) 0.0032(15) C21 0.030(2) 0.042(2) 0.024(2) 0.0049(18) 0.0028(17) -0.0039(18) C22 0.038(2) 0.033(2) 0.028(2) 0.0049(17) 0.0129(17) 0.0002(18) C23 0.0229(19) 0.0212(19) 0.028(2) 0.0031(16) 0.0099(16) 0.0002(15) C24 0.0253(19) 0.021(2) 0.033(2) -0.0008(16) 0.0133(17) -0.0073(15) C25 0.031(2) 0.028(2) 0.049(3) -0.0075(19) 0.024(2) -0.0039(18) C26 0.028(2) 0.020(2) 0.076(3) 0.004(2) 0.028(2) 0.0041(17) C27 0.024(2) 0.030(2) 0.059(3) 0.019(2) 0.0101(19) 0.0022(17) C28 0.026(2) 0.026(2) 0.035(2) 0.0088(17) 0.0080(17) 0.0024(17) C29 0.041(2) 0.037(2) 0.026(2) 0.0036(18) 0.0124(18) 0.0010(19) C30 0.051(3) 0.053(3) 0.034(2) 0.016(2) 0.003(2) 0.014(2) N2 0.0249(16) 0.0210(16) 0.0251(16) 0.0033(13) 0.0103(13) 0.0031(13) C31 0.0196(18) 0.026(2) 0.025(2) -0.0005(16) 0.0083(15) -0.0006(15) C32 0.035(2) 0.027(2) 0.029(2) -0.0006(17) 0.0108(17) 0.0001(17) C33 0.0270(19) 0.028(2) 0.029(2) 0.0041(17) 0.0132(16) 0.0090(16) C34 0.0185(18) 0.022(2) 0.029(2) 0.0051(16) 0.0090(15) 0.0068(15) C35 0.033(2) 0.033(2) 0.025(2) 0.0078(17) 0.0084(17) 0.0099(17) C36 0.031(2) 0.030(2) 0.040(2) 0.0098(18) 0.0138(18) 0.0124(17) C37 0.025(2) 0.022(2) 0.039(2) 0.0017(17) 0.0093(17) 0.0047(16) C38 0.0201(18) 0.022(2) 0.0258(19) 0.0018(16) 0.0043(15) 0.0015(15) C39 0.0189(18) 0.024(2) 0.027(2) -0.0003(16) 0.0068(15) 0.0031(15) C40 0.0246(19) 0.023(2) 0.028(2) 0.0018(16) 0.0105(16) 0.0004(15) C41 0.028(2) 0.027(2) 0.031(2) 0.0049(17) 0.0126(17) 0.0007(16) C42 0.0225(19) 0.025(2) 0.026(2) -0.0017(16) 0.0069(16) 0.0013(15) C43 0.054(3) 0.032(2) 0.049(3) 0.010(2) 0.025(2) 0.008(2) C44 0.033(2) 0.027(2) 0.035(2) 0.0018(17) 0.0044(17) -0.0026(17) C45 0.0268(19) 0.0156(18) 0.026(2) -0.0020(15) 0.0092(16) -0.0014(15) C46 0.028(2) 0.021(2) 0.032(2) -0.0039(16) 0.0115(17) -0.0031(16) C47 0.032(2) 0.025(2) 0.043(2) 0.0013(18) 0.0212(19) -0.0019(17) C48 0.056(3) 0.022(2) 0.038(2) 0.0076(18) 0.023(2) 0.0033(19) C49 0.048(3) 0.024(2) 0.033(2) 0.0080(18) 0.0111(19) 0.0080(18) C50 0.032(2) 0.025(2) 0.034(2) 0.0010(17) 0.0129(18) 0.0066(17) C51 0.026(2) 0.047(3) 0.041(2) -0.005(2) 0.0096(18) -0.0011(18) C52 0.038(2) 0.039(2) 0.035(2) 0.0073(19) 0.0133(19) 0.0146(19) C53 0.037(2) 0.023(2) 0.030(2) 0.0032(16) 0.0136(18) -0.0006(17) C54 0.040(2) 0.037(2) 0.029(2) 0.0078(19) -0.0019(18) -0.0016(19) C55 0.063(3) 0.038(3) 0.027(2) 0.007(2) -0.010(2) -0.010(2) C56 0.094(4) 0.030(3) 0.020(2) -0.0060(19) 0.009(2) 0.006(3) C57 0.072(3) 0.031(2) 0.033(2) 0.004(2) 0.024(2) 0.008(2) C58 0.055(3) 0.026(2) 0.033(2) 0.0067(18) 0.024(2) 0.0032(19) C59 0.034(3) 0.081(4) 0.069(3) 0.014(3) -0.005(2) 0.004(3) C60 0.045(3) 0.042(3) 0.080(3) 0.001(2) 0.036(3) 0.000(2) _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 1.381(4) . ? N1 C4 1.395(4) . ? N1 C1 1.413(4) . ? C1 C2 1.368(5) . ? C1 C12 1.417(5) . ? C2 C3 1.442(5) . ? C2 H1 0.9500 . ? C3 C5 1.384(5) . ? C3 C4 1.415(4) . ? C4 C8 1.410(5) . ? C5 C6 1.401(5) . ? C5 H2 0.9500 . ? C6 C7 1.389(5) . ? C6 C13 1.524(5) . ? C7 C8 1.393(5) . ? C7 H3 0.9500 . ? C8 C14 1.480(5) . ? C9 C10 1.365(5) . ? C9 H4 0.9500 . ? C10 C11 1.425(4) . ? C10 C15 1.498(4) . ? C11 C12 1.373(4) . ? C11 H5 0.9500 . ? C12 C23 1.494(4) . ? C13 H6 0.9800 . ? C13 H7 0.9800 . ? C13 H8 0.9800 . ? C14 H9 0.9800 . ? C14 H10 0.9800 . ? C14 H11 0.9800 . ? C15 C16 1.394(4) . ? C15 C20 1.413(4) . ? C16 C17 1.401(4) . ? C16 C21 1.512(4) . ? C17 C18 1.381(5) . ? C17 H12 0.9500 . ? C18 C19 1.376(5) . ? C18 H13 0.9500 . ? C19 C20 1.399(5) . ? C19 H14 0.9500 . ? C20 C22 1.504(5) . ? C21 H15 0.9800 . ? C21 H16 0.9800 . ? C21 H17 0.9800 . ? C22 H18 0.9800 . ? C22 H19 0.9800 . ? C22 H20 0.9800 . ? C23 C28 1.402(5) . ? C23 C24 1.409(5) . ? C24 C25 1.395(5) . ? C24 C29 1.494(5) . ? C25 C26 1.379(5) . ? C25 H21 0.9500 . ? C26 C27 1.376(5) . ? C26 H22 0.9500 . ? C27 C28 1.380(5) . ? C27 H23 0.9500 . ? C28 C30 1.515(5) . ? C29 H24 0.9800 . ? C29 H25 0.9800 . ? C29 H26 0.9800 . ? C30 H27 0.9800 . ? C30 H28 0.9800 . ? C30 H29 0.9800 . ? N2 C39 1.384(4) . ? N2 C34 1.402(4) . ? N2 C31 1.415(4) . ? C31 C32 1.371(5) . ? C31 C42 1.432(5) . ? C32 C33 1.424(5) . ? C32 H30 0.9500 . ? C33 C35 1.399(5) . ? C33 C34 1.424(5) . ? C34 C38 1.405(5) . ? C35 C36 1.374(5) . ? C35 H31 0.9500 . ? C36 C37 1.404(5) . ? C36 C43 1.519(5) . ? C37 C38 1.384(5) . ? C37 H32 0.9500 . ? C38 C44 1.511(5) . ? C39 C40 1.357(5) . ? C39 H33 0.9500 . ? C40 C41 1.437(5) . ? C40 C45 1.501(5) . ? C41 C42 1.354(5) . ? C41 H34 0.9500 . ? C42 C53 1.491(5) . ? C43 H35 0.9800 . ? C43 H36 0.9800 . ? C43 H37 0.9800 . ? C44 H38 0.9800 . ? C44 H39 0.9800 . ? C44 H40 0.9800 . ? C45 C46 1.399(4) . ? C45 C50 1.401(5) . ? C46 C47 1.390(5) . ? C46 C51 1.507(5) . ? C47 C48 1.374(5) . ? C47 H41 0.9500 . ? C48 C49 1.390(5) . ? C48 H42 0.9500 . ? C49 C50 1.389(5) . ? C49 H43 0.9500 . ? C50 C52 1.511(5) . ? C51 H44 0.9800 . ? C51 H45 0.9800 . ? C51 H46 0.9800 . ? C52 H47 0.9800 . ? C52 H48 0.9800 . ? C52 H49 0.9800 . ? C53 C54 1.394(5) . ? C53 C58 1.405(5) . ? C54 C55 1.400(5) . ? C54 C59 1.517(6) . ? C55 C56 1.382(6) . ? C55 H50 0.9500 . ? C56 C57 1.348(6) . ? C56 H51 0.9500 . ? C57 C58 1.383(5) . ? C57 H52 0.9500 . ? C58 C60 1.505(6) . ? C59 H53 0.9800 . ? C59 H54 0.9800 . ? C59 H55 0.9800 . ? C60 H56 0.9800 . ? C60 H57 0.9800 . ? C60 H58 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 C4 129.2(3) . . ? C9 N1 C1 120.7(3) . . ? C4 N1 C1 110.0(3) . . ? C2 C1 N1 107.6(3) . . ? C2 C1 C12 133.2(3) . . ? N1 C1 C12 119.2(3) . . ? C1 C2 C3 108.3(3) . . ? C1 C2 H1 125.8 . . ? C3 C2 H1 125.8 . . ? C5 C3 C4 121.2(3) . . ? C5 C3 C2 131.2(3) . . ? C4 C3 C2 107.6(3) . . ? N1 C4 C8 131.9(3) . . ? N1 C4 C3 106.4(3) . . ? C8 C4 C3 121.7(3) . . ? C3 C5 C6 118.1(3) . . ? C3 C5 H2 121.0 . . ? C6 C5 H2 121.0 . . ? C7 C6 C5 119.6(4) . . ? C7 C6 C13 119.6(4) . . ? C5 C6 C13 120.8(3) . . ? C6 C7 C8 124.6(4) . . ? C6 C7 H3 117.7 . . ? C8 C7 H3 117.7 . . ? C7 C8 C4 114.8(3) . . ? C7 C8 C14 119.6(4) . . ? C4 C8 C14 125.6(3) . . ? C10 C9 N1 120.7(3) . . ? C10 C9 H4 119.6 . . ? N1 C9 H4 119.6 . . ? C9 C10 C11 119.0(3) . . ? C9 C10 C15 119.9(3) . . ? C11 C10 C15 121.1(3) . . ? C12 C11 C10 121.8(3) . . ? C12 C11 H5 119.1 . . ? C10 C11 H5 119.1 . . ? C11 C12 C1 118.6(3) . . ? C11 C12 C23 121.0(3) . . ? C1 C12 C23 120.4(3) . . ? C6 C13 H6 109.5 . . ? C6 C13 H7 109.5 . . ? H6 C13 H7 109.5 . . ? C6 C13 H8 109.5 . . ? H6 C13 H8 109.5 . . ? H7 C13 H8 109.5 . . ? C8 C14 H9 109.5 . . ? C8 C14 H10 109.5 . . ? H9 C14 H10 109.5 . . ? C8 C14 H11 109.5 . . ? H9 C14 H11 109.5 . . ? H10 C14 H11 109.5 . . ? C16 C15 C20 120.8(3) . . ? C16 C15 C10 120.2(3) . . ? C20 C15 C10 119.0(3) . . ? C15 C16 C17 118.7(3) . . ? C15 C16 C21 121.6(3) . . ? C17 C16 C21 119.6(3) . . ? C18 C17 C16 121.1(3) . . ? C18 C17 H12 119.4 . . ? C16 C17 H12 119.4 . . ? C19 C18 C17 119.7(3) . . ? C19 C18 H13 120.2 . . ? C17 C18 H13 120.2 . . ? C18 C19 C20 121.5(3) . . ? C18 C19 H14 119.2 . . ? C20 C19 H14 119.2 . . ? C19 C20 C15 118.1(3) . . ? C19 C20 C22 120.5(3) . . ? C15 C20 C22 121.3(3) . . ? C16 C21 H15 109.5 . . ? C16 C21 H16 109.5 . . ? H15 C21 H16 109.5 . . ? C16 C21 H17 109.5 . . ? H15 C21 H17 109.5 . . ? H16 C21 H17 109.5 . . ? C20 C22 H18 109.5 . . ? C20 C22 H19 109.5 . . ? H18 C22 H19 109.5 . . ? C20 C22 H20 109.5 . . ? H18 C22 H20 109.5 . . ? H19 C22 H20 109.5 . . ? C28 C23 C24 120.2(3) . . ? C28 C23 C12 120.5(3) . . ? C24 C23 C12 119.2(3) . . ? C25 C24 C23 118.4(3) . . ? C25 C24 C29 120.4(3) . . ? C23 C24 C29 121.2(3) . . ? C26 C25 C24 121.4(4) . . ? C26 C25 H21 119.3 . . ? C24 C25 H21 119.3 . . ? C27 C26 C25 119.2(3) . . ? C27 C26 H22 120.4 . . ? C25 C26 H22 120.4 . . ? C26 C27 C28 121.8(4) . . ? C26 C27 H23 119.1 . . ? C28 C27 H23 119.1 . . ? C27 C28 C23 119.0(3) . . ? C27 C28 C30 120.4(3) . . ? C23 C28 C30 120.7(3) . . ? C24 C29 H24 109.5 . . ? C24 C29 H25 109.5 . . ? H24 C29 H25 109.5 . . ? C24 C29 H26 109.5 . . ? H24 C29 H26 109.5 . . ? H25 C29 H26 109.5 . . ? C28 C30 H27 109.5 . . ? C28 C30 H28 109.5 . . ? H27 C30 H28 109.5 . . ? C28 C30 H29 109.5 . . ? H27 C30 H29 109.5 . . ? H28 C30 H29 109.5 . . ? C39 N2 C34 130.1(3) . . ? C39 N2 C31 121.4(3) . . ? C34 N2 C31 108.4(3) . . ? C32 C31 N2 109.0(3) . . ? C32 C31 C42 132.9(3) . . ? N2 C31 C42 118.1(3) . . ? C31 C32 C33 107.8(3) . . ? C31 C32 H30 126.1 . . ? C33 C32 H30 126.1 . . ? C35 C33 C34 119.7(3) . . ? C35 C33 C32 132.2(3) . . ? C34 C33 C32 108.0(3) . . ? N2 C34 C38 131.5(3) . . ? N2 C34 C33 106.7(3) . . ? C38 C34 C33 121.8(3) . . ? C36 C35 C33 119.3(3) . . ? C36 C35 H31 120.3 . . ? C33 C35 H31 120.3 . . ? C35 C36 C37 119.6(3) . . ? C35 C36 C43 121.7(3) . . ? C37 C36 C43 118.7(3) . . ? C38 C37 C36 124.1(3) . . ? C38 C37 H32 118.0 . . ? C36 C37 H32 118.0 . . ? C37 C38 C34 115.5(3) . . ? C37 C38 C44 119.5(3) . . ? C34 C38 C44 125.0(3) . . ? C40 C39 N2 120.4(3) . . ? C40 C39 H33 119.8 . . ? N2 C39 H33 119.8 . . ? C39 C40 C41 118.9(3) . . ? C39 C40 C45 121.0(3) . . ? C41 C40 C45 120.1(3) . . ? C42 C41 C40 122.1(3) . . ? C42 C41 H34 118.9 . . ? C40 C41 H34 118.9 . . ? C41 C42 C31 118.9(3) . . ? C41 C42 C53 122.1(3) . . ? C31 C42 C53 119.0(3) . . ? C36 C43 H35 109.5 . . ? C36 C43 H36 109.5 . . ? H35 C43 H36 109.5 . . ? C36 C43 H37 109.5 . . ? H35 C43 H37 109.5 . . ? H36 C43 H37 109.5 . . ? C38 C44 H38 109.5 . . ? C38 C44 H39 109.5 . . ? H38 C44 H39 109.5 . . ? C38 C44 H40 109.5 . . ? H38 C44 H40 109.5 . . ? H39 C44 H40 109.5 . . ? C46 C45 C50 120.8(3) . . ? C46 C45 C40 119.3(3) . . ? C50 C45 C40 119.9(3) . . ? C47 C46 C45 118.5(3) . . ? C47 C46 C51 120.4(3) . . ? C45 C46 C51 121.2(3) . . ? C48 C47 C46 121.3(3) . . ? C48 C47 H41 119.3 . . ? C46 C47 H41 119.3 . . ? C47 C48 C49 120.0(3) . . ? C47 C48 H42 120.0 . . ? C49 C48 H42 120.0 . . ? C50 C49 C48 120.4(4) . . ? C50 C49 H43 119.8 . . ? C48 C49 H43 119.8 . . ? C49 C50 C45 119.1(3) . . ? C49 C50 C52 120.5(3) . . ? C45 C50 C52 120.4(3) . . ? C46 C51 H44 109.5 . . ? C46 C51 H45 109.5 . . ? H44 C51 H45 109.5 . . ? C46 C51 H46 109.5 . . ? H44 C51 H46 109.5 . . ? H45 C51 H46 109.5 . . ? C50 C52 H47 109.5 . . ? C50 C52 H48 109.5 . . ? H47 C52 H48 109.5 . . ? C50 C52 H49 109.5 . . ? H47 C52 H49 109.5 . . ? H48 C52 H49 109.5 . . ? C54 C53 C58 119.9(3) . . ? C54 C53 C42 120.4(3) . . ? C58 C53 C42 119.6(3) . . ? C53 C54 C55 118.6(4) . . ? C53 C54 C59 120.9(4) . . ? C55 C54 C59 120.4(4) . . ? C56 C55 C54 120.5(4) . . ? C56 C55 H50 119.7 . . ? C54 C55 H50 119.7 . . ? C57 C56 C55 120.3(4) . . ? C57 C56 H51 119.8 . . ? C55 C56 H51 119.8 . . ? C56 C57 C58 121.5(4) . . ? C56 C57 H52 119.3 . . ? C58 C57 H52 119.3 . . ? C57 C58 C53 119.1(4) . . ? C57 C58 C60 119.8(4) . . ? C53 C58 C60 121.1(3) . . ? C54 C59 H53 109.5 . . ? C54 C59 H54 109.5 . . ? H53 C59 H54 109.5 . . ? C54 C59 H55 109.5 . . ? H53 C59 H55 109.5 . . ? H54 C59 H55 109.5 . . ? C58 C60 H56 109.5 . . ? C58 C60 H57 109.5 . . ? H56 C60 H57 109.5 . . ? C58 C60 H58 109.5 . . ? H56 C60 H58 109.5 . . ? H57 C60 H58 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 C9 N1 C1 C2 -178.0(3) . . . . ? C4 N1 C1 C2 0.2(4) . . . . ? C9 N1 C1 C12 0.7(4) . . . . ? C4 N1 C1 C12 179.0(3) . . . . ? N1 C1 C2 C3 -0.2(4) . . . . ? C12 C1 C2 C3 -178.7(3) . . . . ? C1 C2 C3 C5 -179.7(4) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C9 N1 C4 C8 -4.0(6) . . . . ? C1 N1 C4 C8 177.9(3) . . . . ? C9 N1 C4 C3 177.9(3) . . . . ? C1 N1 C4 C3 -0.2(4) . . . . ? C5 C3 C4 N1 179.9(3) . . . . ? C2 C3 C4 N1 0.1(4) . . . . ? C5 C3 C4 C8 1.6(5) . . . . ? C2 C3 C4 C8 -178.2(3) . . . . ? C4 C3 C5 C6 0.0(5) . . . . ? C2 C3 C5 C6 179.8(4) . . . . ? C3 C5 C6 C7 -0.5(5) . . . . ? C3 C5 C6 C13 -179.8(4) . . . . ? C5 C6 C7 C8 -0.6(6) . . . . ? C13 C6 C7 C8 178.6(4) . . . . ? C6 C7 C8 C4 2.2(5) . . . . ? C6 C7 C8 C14 -178.3(3) . . . . ? N1 C4 C8 C7 179.6(3) . . . . ? C3 C4 C8 C7 -2.6(5) . . . . ? N1 C4 C8 C14 0.0(6) . . . . ? C3 C4 C8 C14 177.9(3) . . . . ? C4 N1 C9 C10 -176.9(3) . . . . ? C1 N1 C9 C10 1.0(5) . . . . ? N1 C9 C10 C11 -1.7(5) . . . . ? N1 C9 C10 C15 178.9(3) . . . . ? C9 C10 C11 C12 0.6(5) . . . . ? C15 C10 C11 C12 -180.0(3) . . . . ? C10 C11 C12 C1 1.1(5) . . . . ? C10 C11 C12 C23 -179.9(3) . . . . ? C2 C1 C12 C11 176.7(4) . . . . ? N1 C1 C12 C11 -1.7(4) . . . . ? C2 C1 C12 C23 -2.3(6) . . . . ? N1 C1 C12 C23 179.3(3) . . . . ? C9 C10 C15 C16 -103.8(4) . . . . ? C11 C10 C15 C16 76.8(4) . . . . ? C9 C10 C15 C20 76.7(4) . . . . ? C11 C10 C15 C20 -102.7(4) . . . . ? C20 C15 C16 C17 -1.6(5) . . . . ? C10 C15 C16 C17 178.8(3) . . . . ? C20 C15 C16 C21 179.9(3) . . . . ? C10 C15 C16 C21 0.4(5) . . . . ? C15 C16 C17 C18 1.6(5) . . . . ? C21 C16 C17 C18 -179.9(3) . . . . ? C16 C17 C18 C19 0.1(5) . . . . ? C17 C18 C19 C20 -1.9(5) . . . . ? C18 C19 C20 C15 1.9(5) . . . . ? C18 C19 C20 C22 -175.3(3) . . . . ? C16 C15 C20 C19 -0.1(5) . . . . ? C10 C15 C20 C19 179.5(3) . . . . ? C16 C15 C20 C22 177.1(3) . . . . ? C10 C15 C20 C22 -3.4(5) . . . . ? C11 C12 C23 C28 102.6(4) . . . . ? C1 C12 C23 C28 -78.4(4) . . . . ? C11 C12 C23 C24 -75.1(4) . . . . ? C1 C12 C23 C24 103.9(4) . . . . ? C28 C23 C24 C25 -1.2(5) . . . . ? C12 C23 C24 C25 176.5(3) . . . . ? C28 C23 C24 C29 -180.0(3) . . . . ? C12 C23 C24 C29 -2.2(5) . . . . ? C23 C24 C25 C26 -0.7(5) . . . . ? C29 C24 C25 C26 178.1(3) . . . . ? C24 C25 C26 C27 1.9(5) . . . . ? C25 C26 C27 C28 -1.2(5) . . . . ? C26 C27 C28 C23 -0.6(5) . . . . ? C26 C27 C28 C30 -179.8(3) . . . . ? C24 C23 C28 C27 1.8(5) . . . . ? C12 C23 C28 C27 -175.9(3) . . . . ? C24 C23 C28 C30 -178.9(3) . . . . ? C12 C23 C28 C30 3.4(5) . . . . ? C39 N2 C31 C32 177.0(3) . . . . ? C34 N2 C31 C32 -0.6(3) . . . . ? C39 N2 C31 C42 -4.1(4) . . . . ? C34 N2 C31 C42 178.3(3) . . . . ? N2 C31 C32 C33 0.4(4) . . . . ? C42 C31 C32 C33 -178.3(3) . . . . ? C31 C32 C33 C35 178.6(3) . . . . ? C31 C32 C33 C34 0.0(4) . . . . ? C39 N2 C34 C38 4.2(5) . . . . ? C31 N2 C34 C38 -178.4(3) . . . . ? C39 N2 C34 C33 -176.8(3) . . . . ? C31 N2 C34 C33 0.6(3) . . . . ? C35 C33 C34 N2 -179.2(3) . . . . ? C32 C33 C34 N2 -0.4(3) . . . . ? C35 C33 C34 C38 -0.1(5) . . . . ? C32 C33 C34 C38 178.7(3) . . . . ? C34 C33 C35 C36 -0.1(5) . . . . ? C32 C33 C35 C36 -178.6(4) . . . . ? C33 C35 C36 C37 -0.1(5) . . . . ? C33 C35 C36 C43 -178.4(3) . . . . ? C35 C36 C37 C38 0.5(5) . . . . ? C43 C36 C37 C38 178.9(3) . . . . ? C36 C37 C38 C34 -0.6(5) . . . . ? C36 C37 C38 C44 177.5(3) . . . . ? N2 C34 C38 C37 179.3(3) . . . . ? C33 C34 C38 C37 0.4(4) . . . . ? N2 C34 C38 C44 1.3(5) . . . . ? C33 C34 C38 C44 -177.6(3) . . . . ? C34 N2 C39 C40 178.6(3) . . . . ? C31 N2 C39 C40 1.5(5) . . . . ? N2 C39 C40 C41 1.9(5) . . . . ? N2 C39 C40 C45 -177.7(3) . . . . ? C39 C40 C41 C42 -2.9(5) . . . . ? C45 C40 C41 C42 176.8(3) . . . . ? C40 C41 C42 C31 0.3(5) . . . . ? C40 C41 C42 C53 -179.9(3) . . . . ? C32 C31 C42 C41 -178.3(3) . . . . ? N2 C31 C42 C41 3.1(5) . . . . ? C32 C31 C42 C53 1.8(6) . . . . ? N2 C31 C42 C53 -176.8(3) . . . . ? C39 C40 C45 C46 90.3(4) . . . . ? C41 C40 C45 C46 -89.4(4) . . . . ? C39 C40 C45 C50 -92.7(4) . . . . ? C41 C40 C45 C50 87.7(4) . . . . ? C50 C45 C46 C47 1.7(5) . . . . ? C40 C45 C46 C47 178.7(3) . . . . ? C50 C45 C46 C51 -178.4(3) . . . . ? C40 C45 C46 C51 -1.3(5) . . . . ? C45 C46 C47 C48 -1.2(5) . . . . ? C51 C46 C47 C48 178.9(3) . . . . ? C46 C47 C48 C49 0.2(6) . . . . ? C47 C48 C49 C50 0.4(6) . . . . ? C48 C49 C50 C45 0.1(5) . . . . ? C48 C49 C50 C52 -178.7(3) . . . . ? C46 C45 C50 C49 -1.2(5) . . . . ? C40 C45 C50 C49 -178.2(3) . . . . ? C46 C45 C50 C52 177.7(3) . . . . ? C40 C45 C50 C52 0.6(5) . . . . ? C41 C42 C53 C54 71.7(5) . . . . ? C31 C42 C53 C54 -108.5(4) . . . . ? C41 C42 C53 C58 -105.0(4) . . . . ? C31 C42 C53 C58 74.9(4) . . . . ? C58 C53 C54 C55 3.1(5) . . . . ? C42 C53 C54 C55 -173.5(3) . . . . ? C58 C53 C54 C59 -178.1(4) . . . . ? C42 C53 C54 C59 5.3(6) . . . . ? C53 C54 C55 C56 -2.8(6) . . . . ? C59 C54 C55 C56 178.4(4) . . . . ? C54 C55 C56 C57 1.1(6) . . . . ? C55 C56 C57 C58 0.3(6) . . . . ? C56 C57 C58 C53 0.1(6) . . . . ? C56 C57 C58 C60 177.8(4) . . . . ? C54 C53 C58 C57 -1.8(5) . . . . ? C42 C53 C58 C57 174.8(3) . . . . ? C54 C53 C58 C60 -179.5(4) . . . . ? C42 C53 C58 C60 -2.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.621 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.056