# 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_FO4120 _database_code_depnum_ccdc_archive 'CCDC 873551' #TrackingRef 'chemcom.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H21 N' _chemical_formula_sum 'C28 H21 N' _chemical_formula_weight 371.46 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 11.0644(4) _cell_length_b 10.4214(5) _cell_length_c 17.6016(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.730(3) _cell_angle_gamma 90.00 _cell_volume 2011.14(15) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 11402 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11402 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4568 _reflns_number_gt 3738 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0397P)^2^+1.0922P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4568 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.41100(11) 0.89762(12) 0.22042(7) 0.0217(3) Uani 1 1 d . . . C1 C 0.41363(12) 1.02954(14) 0.24161(8) 0.0215(3) Uani 1 1 d . . . C2 C 0.40891(13) 1.06413(15) 0.31527(8) 0.0240(3) Uani 1 1 d . . . H2 H 0.4219(15) 1.1545(17) 0.3308(9) 0.023(4) Uiso 1 1 d . . . C3 C 0.38966(13) 0.97850(15) 0.37516(8) 0.0240(3) Uani 1 1 d . . . C4 C 0.37120(13) 0.91347(15) 0.42876(8) 0.0243(3) Uani 1 1 d . . . C5 C 0.33823(13) 0.83561(15) 0.48999(8) 0.0225(3) Uani 1 1 d . . . C6 C 0.31887(15) 0.89170(16) 0.55979(9) 0.0283(3) Uani 1 1 d . . . H6 H 0.3338(16) 0.9842(19) 0.5675(10) 0.033(5) Uiso 1 1 d . . . C7 C 0.27960(16) 0.81695(17) 0.61663(9) 0.0321(4) Uani 1 1 d . . . H7 H 0.2665(18) 0.858(2) 0.6665(12) 0.044(6) Uiso 1 1 d . . . C8 C 0.26117(15) 0.68602(17) 0.60564(9) 0.0302(4) Uani 1 1 d . . . H8 H 0.2316(18) 0.634(2) 0.6478(11) 0.043(5) Uiso 1 1 d . . . C9 C 0.28187(14) 0.62945(16) 0.53714(9) 0.0272(3) Uani 1 1 d . . . H9 H 0.2712(17) 0.5343(19) 0.5269(11) 0.037(5) Uiso 1 1 d . . . C10 C 0.32035(13) 0.70381(15) 0.47977(9) 0.0248(3) Uani 1 1 d . . . H10 H 0.3333(17) 0.6643(19) 0.4308(11) 0.037(5) Uiso 1 1 d . . . C11 C 0.43204(13) 1.12442(14) 0.18157(8) 0.0220(3) Uani 1 1 d . . . C12 C 0.48635(13) 1.08696(16) 0.11779(9) 0.0240(3) Uani 1 1 d . . . H12 H 0.5098(16) 0.9968(18) 0.1128(10) 0.029(5) Uiso 1 1 d . . . C13 C 0.50968(14) 1.17569(17) 0.06305(9) 0.0292(4) Uani 1 1 d . . . H13 H 0.5472(16) 1.1471(18) 0.0185(11) 0.032(5) Uiso 1 1 d . . . C14 C 0.47923(14) 1.30377(17) 0.07080(10) 0.0309(4) Uani 1 1 d . . . H14 H 0.4960(18) 1.367(2) 0.0313(12) 0.047(6) Uiso 1 1 d . . . C15 C 0.42479(14) 1.34250(16) 0.13354(10) 0.0296(4) Uani 1 1 d . . . H15 H 0.4013(18) 1.433(2) 0.1404(12) 0.047(6) Uiso 1 1 d . . . C16 C 0.40018(14) 1.25333(15) 0.18799(9) 0.0265(3) Uani 1 1 d . . . H16 H 0.3600(17) 1.2806(19) 0.2322(11) 0.038(5) Uiso 1 1 d . . . C17 C 0.32514(13) 0.85563(14) 0.15827(8) 0.0211(3) Uani 1 1 d . . . C18 C 0.35271(14) 0.75728(15) 0.10944(9) 0.0254(3) Uani 1 1 d . . . H18 H 0.4332(17) 0.7154(18) 0.1184(11) 0.034(5) Uiso 1 1 d . . . C19 C 0.26741(15) 0.71940(16) 0.04845(9) 0.0286(3) Uani 1 1 d . . . H19 H 0.2881(17) 0.6496(19) 0.0148(11) 0.037(5) Uiso 1 1 d . . . C20 C 0.15483(15) 0.77899(17) 0.03424(9) 0.0301(4) Uani 1 1 d . . . H20 H 0.0956(17) 0.7503(18) -0.0087(11) 0.037(5) Uiso 1 1 d . . . C21 C 0.12716(14) 0.87779(16) 0.08180(9) 0.0276(3) Uani 1 1 d . . . H21 H 0.0449(17) 0.9233(18) 0.0730(10) 0.034(5) Uiso 1 1 d . . . C22 C 0.21167(13) 0.91573(15) 0.14389(9) 0.0243(3) Uani 1 1 d . . . H22 H 0.1907(15) 0.9847(17) 0.1785(10) 0.027(4) Uiso 1 1 d . . . C23 C 0.50145(13) 0.81357(14) 0.25727(8) 0.0215(3) Uani 1 1 d . . . C24 C 0.61940(14) 0.85909(16) 0.28022(8) 0.0243(3) Uani 1 1 d . . . H24 H 0.6379(15) 0.9490(17) 0.2725(10) 0.025(4) Uiso 1 1 d . . . C25 C 0.70885(14) 0.77734(17) 0.31535(9) 0.0286(3) Uani 1 1 d . . . H25 H 0.7902(17) 0.8110(18) 0.3312(10) 0.031(5) Uiso 1 1 d . . . C26 C 0.68266(15) 0.64968(17) 0.32751(9) 0.0311(4) Uani 1 1 d . . . H26 H 0.7467(18) 0.592(2) 0.3522(11) 0.044(6) Uiso 1 1 d . . . C27 C 0.56558(15) 0.60396(17) 0.30470(10) 0.0315(4) Uani 1 1 d . . . H27 H 0.5471(17) 0.513(2) 0.3142(11) 0.038(5) Uiso 1 1 d . . . C28 C 0.47505(14) 0.68554(16) 0.27076(9) 0.0277(3) Uani 1 1 d . . . H28 H 0.3924(17) 0.6533(18) 0.2551(10) 0.033(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0250(6) 0.0204(6) 0.0191(6) -0.0009(5) 0.0004(5) 0.0010(5) C1 0.0195(7) 0.0217(7) 0.0227(7) 0.0002(6) 0.0015(5) 0.0000(5) C2 0.0271(7) 0.0226(8) 0.0226(7) -0.0006(6) 0.0044(6) -0.0001(6) C3 0.0267(7) 0.0234(8) 0.0221(7) -0.0032(6) 0.0039(6) 0.0013(6) C4 0.0248(7) 0.0267(8) 0.0214(7) -0.0020(6) 0.0028(6) 0.0004(6) C5 0.0215(7) 0.0256(8) 0.0203(7) 0.0027(6) 0.0021(5) 0.0012(6) C6 0.0365(8) 0.0253(8) 0.0228(7) -0.0006(6) 0.0033(6) -0.0024(7) C7 0.0430(9) 0.0316(9) 0.0227(8) -0.0014(7) 0.0086(7) -0.0018(7) C8 0.0350(8) 0.0309(9) 0.0259(8) 0.0046(7) 0.0077(6) -0.0024(7) C9 0.0289(8) 0.0232(8) 0.0293(8) 0.0009(6) 0.0034(6) 0.0003(6) C10 0.0246(7) 0.0267(8) 0.0227(7) -0.0015(6) 0.0014(6) 0.0022(6) C11 0.0207(7) 0.0239(7) 0.0210(7) 0.0011(6) 0.0016(5) -0.0015(6) C12 0.0219(7) 0.0273(8) 0.0225(7) 0.0004(6) 0.0015(5) -0.0023(6) C13 0.0245(7) 0.0394(9) 0.0242(8) 0.0021(7) 0.0050(6) -0.0060(7) C14 0.0270(8) 0.0344(9) 0.0302(8) 0.0111(7) 0.0002(6) -0.0065(7) C15 0.0287(8) 0.0253(8) 0.0338(9) 0.0061(7) 0.0006(6) -0.0002(6) C16 0.0267(7) 0.0258(8) 0.0268(8) 0.0001(6) 0.0032(6) 0.0006(6) C17 0.0233(7) 0.0214(7) 0.0192(7) 0.0021(6) 0.0047(5) -0.0039(6) C18 0.0250(7) 0.0256(8) 0.0266(8) -0.0020(6) 0.0067(6) -0.0023(6) C19 0.0315(8) 0.0302(9) 0.0256(8) -0.0047(7) 0.0089(6) -0.0097(7) C20 0.0293(8) 0.0380(9) 0.0223(7) 0.0020(7) 0.0008(6) -0.0116(7) C21 0.0244(7) 0.0309(9) 0.0269(8) 0.0073(7) 0.0017(6) -0.0033(6) C22 0.0257(7) 0.0234(8) 0.0241(7) 0.0029(6) 0.0049(6) -0.0006(6) C23 0.0238(7) 0.0236(7) 0.0174(6) 0.0003(6) 0.0038(5) 0.0018(6) C24 0.0263(7) 0.0247(8) 0.0221(7) -0.0010(6) 0.0042(6) -0.0007(6) C25 0.0239(8) 0.0357(9) 0.0256(8) -0.0005(7) 0.0008(6) 0.0008(6) C26 0.0293(8) 0.0342(9) 0.0293(8) 0.0065(7) 0.0029(6) 0.0079(7) C27 0.0337(8) 0.0252(8) 0.0359(9) 0.0078(7) 0.0065(7) 0.0023(7) C28 0.0252(7) 0.0268(8) 0.0312(8) 0.0051(7) 0.0039(6) -0.0004(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 C23 1.4196(18) . ? N1 C17 1.4181(18) . ? N1 C1 1.4238(19) . ? C1 C2 1.353(2) . ? C1 C11 1.481(2) . ? C2 C3 1.419(2) . ? C2 H2 0.986(17) . ? C3 C4 1.201(2) . ? C4 C5 1.435(2) . ? C5 C10 1.396(2) . ? C5 C6 1.403(2) . ? C6 C7 1.383(2) . ? C6 H6 0.984(19) . ? C7 C8 1.389(2) . ? C7 H7 1.00(2) . ? C8 C9 1.389(2) . ? C8 H8 1.01(2) . ? C9 C10 1.385(2) . ? C9 H9 1.01(2) . ? C10 H10 0.984(19) . ? C11 C16 1.397(2) . ? C11 C12 1.398(2) . ? C12 C13 1.385(2) . ? C12 H12 0.982(18) . ? C13 C14 1.388(3) . ? C13 H13 0.981(19) . ? C14 C15 1.387(2) . ? C14 H14 0.99(2) . ? C15 C16 1.388(2) . ? C15 H15 0.99(2) . ? C16 H16 0.99(2) . ? C17 C22 1.395(2) . ? C17 C18 1.397(2) . ? C18 C19 1.388(2) . ? C18 H18 0.985(19) . ? C19 C20 1.384(2) . ? C19 H19 0.98(2) . ? C20 C21 1.387(2) . ? C20 H20 0.979(19) . ? C21 C22 1.397(2) . ? C21 H21 1.019(18) . ? C22 H22 0.989(18) . ? C23 C28 1.393(2) . ? C23 C24 1.396(2) . ? C24 C25 1.387(2) . ? C24 H24 0.973(18) . ? C25 C26 1.384(2) . ? C25 H25 0.971(18) . ? C26 C27 1.388(2) . ? C26 H26 0.98(2) . ? C27 C28 1.386(2) . ? C27 H27 0.99(2) . ? C28 H28 0.978(18) . ? 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 C23 N1 C17 121.33(12) . . ? C23 N1 C1 119.19(12) . . ? C17 N1 C1 119.22(12) . . ? C2 C1 N1 120.41(13) . . ? C2 C1 C11 122.17(14) . . ? N1 C1 C11 117.23(13) . . ? C1 C2 C3 124.96(14) . . ? C1 C2 H2 119.8(10) . . ? C3 C2 H2 115.2(10) . . ? C4 C3 C2 175.32(16) . . ? C3 C4 C5 175.04(16) . . ? C10 C5 C6 119.15(14) . . ? C10 C5 C4 120.38(14) . . ? C6 C5 C4 120.42(14) . . ? C7 C6 C5 119.91(15) . . ? C7 C6 H6 121.0(11) . . ? C5 C6 H6 119.1(11) . . ? C6 C7 C8 120.46(16) . . ? C6 C7 H7 119.5(12) . . ? C8 C7 H7 120.1(12) . . ? C9 C8 C7 119.97(15) . . ? C9 C8 H8 121.1(12) . . ? C7 C8 H8 119.0(12) . . ? C10 C9 C8 119.90(15) . . ? C10 C9 H9 117.3(11) . . ? C8 C9 H9 122.8(11) . . ? C9 C10 C5 120.59(15) . . ? C9 C10 H10 120.0(11) . . ? C5 C10 H10 119.4(11) . . ? C16 C11 C12 118.27(14) . . ? C16 C11 C1 121.58(14) . . ? C12 C11 C1 120.11(14) . . ? C13 C12 C11 120.85(15) . . ? C13 C12 H12 120.0(11) . . ? C11 C12 H12 119.1(11) . . ? C12 C13 C14 120.23(15) . . ? C12 C13 H13 119.5(11) . . ? C14 C13 H13 120.3(11) . . ? C13 C14 C15 119.68(15) . . ? C13 C14 H14 120.0(12) . . ? C15 C14 H14 120.3(12) . . ? C14 C15 C16 120.09(16) . . ? C14 C15 H15 121.6(12) . . ? C16 C15 H15 118.3(12) . . ? C15 C16 C11 120.85(15) . . ? C15 C16 H16 120.1(11) . . ? C11 C16 H16 119.0(11) . . ? C22 C17 C18 118.89(14) . . ? C22 C17 N1 119.63(13) . . ? C18 C17 N1 121.45(13) . . ? C19 C18 C17 120.16(15) . . ? C19 C18 H18 120.2(11) . . ? C17 C18 H18 119.6(11) . . ? C20 C19 C18 120.93(16) . . ? C20 C19 H19 119.9(11) . . ? C18 C19 H19 119.2(11) . . ? C19 C20 C21 119.36(15) . . ? C19 C20 H20 119.7(11) . . ? C21 C20 H20 120.9(11) . . ? C20 C21 C22 120.24(15) . . ? C20 C21 H21 121.3(10) . . ? C22 C21 H21 118.5(10) . . ? C17 C22 C21 120.42(15) . . ? C17 C22 H22 119.6(10) . . ? C21 C22 H22 120.0(10) . . ? C28 C23 C24 119.04(14) . . ? C28 C23 N1 121.18(13) . . ? C24 C23 N1 119.78(13) . . ? C25 C24 C23 120.23(15) . . ? C25 C24 H24 120.2(10) . . ? C23 C24 H24 119.5(10) . . ? C26 C25 C24 120.51(15) . . ? C26 C25 H25 120.5(11) . . ? C24 C25 H25 119.0(11) . . ? C25 C26 C27 119.46(15) . . ? C25 C26 H26 120.0(12) . . ? C27 C26 H26 120.5(12) . . ? C28 C27 C26 120.41(16) . . ? C28 C27 H27 120.4(11) . . ? C26 C27 H27 119.2(11) . . ? C27 C28 C23 120.32(15) . . ? C27 C28 H28 120.3(11) . . ? C23 C28 H28 119.4(11) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.227 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.041 data_FO4319 _database_code_depnum_ccdc_archive 'CCDC 873552' #TrackingRef 'chemcom.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H23 N' _chemical_formula_sum 'C25 H23 N' _chemical_formula_weight 337.44 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7453(2) _cell_length_b 11.3478(2) _cell_length_c 17.3880(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.617(1) _cell_angle_gamma 90.00 _cell_volume 1916.66(6) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 11729 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.45 _exptl_crystal_description prism _exptl_crystal_colour light_yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11729 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4345 _reflns_number_gt 3894 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHEXL-97 _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^)+(0.0430P)^2^+0.6979P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4345 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.73359(9) 0.29852(7) 0.01189(5) 0.02047(19) Uani 1 1 d . . . C1 C 0.83091(10) 0.33842(9) 0.06795(5) 0.0187(2) Uani 1 1 d . . . C2 C 0.93441(11) 0.26969(9) 0.10091(6) 0.0215(2) Uani 1 1 d . . . H2 H 0.9373(14) 0.1863(12) 0.0885(8) 0.030(3) Uiso 1 1 d . . . C3 C 1.04659(11) 0.31963(9) 0.14698(6) 0.0219(2) Uani 1 1 d . . . C4 C 1.14217(11) 0.36590(9) 0.18343(6) 0.0226(2) Uani 1 1 d . . . C5 C 1.25064(11) 0.43202(9) 0.22383(6) 0.0215(2) Uani 1 1 d . . . C6 C 1.23284(12) 0.55282(10) 0.23641(6) 0.0274(2) Uani 1 1 d . . . H6 H 1.1446(15) 0.5898(13) 0.2189(8) 0.035(4) Uiso 1 1 d . . . C7 C 1.33868(13) 0.61912(10) 0.27277(7) 0.0316(3) Uani 1 1 d . . . H7 H 1.3236(16) 0.7035(14) 0.2813(9) 0.041(4) Uiso 1 1 d . . . C8 C 1.46299(12) 0.56648(11) 0.29738(6) 0.0288(2) Uani 1 1 d . . . H8 H 1.5379(14) 0.6138(13) 0.3231(8) 0.035(4) Uiso 1 1 d . . . C9 C 1.48047(11) 0.44665(11) 0.28696(6) 0.0273(2) Uani 1 1 d . . . H9 H 1.5666(15) 0.4081(13) 0.3051(8) 0.037(4) Uiso 1 1 d . . . C10 C 1.37552(11) 0.37941(10) 0.25056(6) 0.0250(2) Uani 1 1 d . . . H10 H 1.3871(14) 0.2939(13) 0.2428(8) 0.031(3) Uiso 1 1 d . . . C11 C 0.59603(10) 0.35552(9) 0.00128(6) 0.0206(2) Uani 1 1 d . . . H11 H 0.6149(13) 0.4405(11) 0.0055(7) 0.021(3) Uiso 1 1 d . . . C12 C 0.52874(12) 0.33200(12) -0.07897(6) 0.0302(3) Uani 1 1 d . . . H12C H 0.4426(15) 0.3794(13) -0.0870(8) 0.035(4) Uiso 1 1 d . . . H12B H 0.5900(16) 0.3550(13) -0.1189(9) 0.041(4) Uiso 1 1 d . . . H12A H 0.5052(16) 0.2467(15) -0.0859(9) 0.044(4) Uiso 1 1 d . . . C13 C 0.50303(12) 0.32128(11) 0.06409(7) 0.0277(2) Uani 1 1 d . . . H13C H 0.4151(16) 0.3681(13) 0.0575(8) 0.038(4) Uiso 1 1 d . . . H13B H 0.4785(15) 0.2357(14) 0.0605(8) 0.040(4) Uiso 1 1 d . . . H13A H 0.5500(16) 0.3373(13) 0.1168(9) 0.040(4) Uiso 1 1 d . . . C14 C 0.82713(10) 0.46583(9) 0.08909(6) 0.0190(2) Uani 1 1 d . . . C15 C 0.81261(11) 0.49866(9) 0.16537(6) 0.0231(2) Uani 1 1 d . . . H15 H 0.7981(14) 0.4369(12) 0.2039(8) 0.030(3) Uiso 1 1 d . . . C16 C 0.82118(11) 0.61638(10) 0.18706(6) 0.0270(2) Uani 1 1 d . . . H16 H 0.8123(14) 0.6376(13) 0.2416(8) 0.035(4) Uiso 1 1 d . . . C17 C 0.84414(11) 0.70218(10) 0.13293(7) 0.0280(2) Uani 1 1 d . . . H17 H 0.8505(14) 0.7847(13) 0.1480(8) 0.035(4) Uiso 1 1 d . . . C18 C 0.85728(11) 0.67046(10) 0.05669(7) 0.0259(2) Uani 1 1 d . . . H18 H 0.8727(14) 0.7314(12) 0.0174(8) 0.032(3) Uiso 1 1 d . . . C19 C 0.84823(10) 0.55276(9) 0.03465(6) 0.0213(2) Uani 1 1 d . . . H19 H 0.8596(13) 0.5297(11) -0.0182(8) 0.025(3) Uiso 1 1 d . . . C20 C 0.75072(10) 0.18163(9) -0.01798(6) 0.0214(2) Uani 1 1 d . . . C21 C 0.82633(11) 0.16804(11) -0.08192(6) 0.0265(2) Uani 1 1 d . . . H21 H 0.8636(14) 0.2358(13) -0.1053(8) 0.033(4) Uiso 1 1 d . . . C22 C 0.84831(12) 0.05581(11) -0.11098(7) 0.0327(3) Uani 1 1 d . . . H22 H 0.9029(16) 0.0487(13) -0.1558(9) 0.043(4) Uiso 1 1 d . . . C23 C 0.79395(12) -0.04215(11) -0.07697(7) 0.0341(3) Uani 1 1 d . . . H23 H 0.8079(15) -0.1204(13) -0.0979(8) 0.038(4) Uiso 1 1 d . . . C24 C 0.71885(13) -0.02861(11) -0.01350(8) 0.0339(3) Uani 1 1 d . . . H24 H 0.6829(16) -0.0990(15) 0.0120(9) 0.046(4) Uiso 1 1 d . . . C25 C 0.69750(12) 0.08307(10) 0.01654(7) 0.0283(2) Uani 1 1 d . . . H25 H 0.6471(15) 0.0919(13) 0.0627(8) 0.036(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0177(4) 0.0194(4) 0.0237(4) -0.0047(3) -0.0024(3) 0.0018(3) C1 0.0187(5) 0.0191(5) 0.0184(4) -0.0011(4) 0.0017(3) -0.0005(4) C2 0.0217(5) 0.0183(5) 0.0240(5) -0.0010(4) -0.0018(4) 0.0003(4) C3 0.0223(5) 0.0197(5) 0.0233(5) 0.0020(4) -0.0001(4) 0.0029(4) C4 0.0227(5) 0.0217(5) 0.0230(5) 0.0020(4) -0.0007(4) 0.0017(4) C5 0.0220(5) 0.0244(5) 0.0179(4) 0.0009(4) 0.0007(4) -0.0027(4) C6 0.0279(6) 0.0249(6) 0.0287(5) 0.0008(4) -0.0019(4) 0.0012(4) C7 0.0383(7) 0.0236(6) 0.0321(6) -0.0036(4) -0.0014(5) -0.0033(5) C8 0.0297(6) 0.0331(6) 0.0232(5) -0.0023(4) -0.0006(4) -0.0105(5) C9 0.0204(5) 0.0344(6) 0.0268(5) 0.0007(4) -0.0006(4) -0.0025(4) C10 0.0230(5) 0.0243(5) 0.0274(5) -0.0003(4) 0.0012(4) -0.0006(4) C11 0.0182(5) 0.0200(5) 0.0231(5) -0.0006(4) -0.0014(4) 0.0020(4) C12 0.0239(5) 0.0417(7) 0.0240(5) -0.0036(5) -0.0042(4) 0.0059(5) C13 0.0237(5) 0.0314(6) 0.0285(6) 0.0032(4) 0.0038(4) 0.0044(5) C14 0.0147(4) 0.0194(5) 0.0226(5) -0.0024(4) -0.0009(3) 0.0013(4) C15 0.0234(5) 0.0237(5) 0.0219(5) -0.0016(4) -0.0003(4) 0.0014(4) C16 0.0259(5) 0.0284(6) 0.0263(5) -0.0083(4) 0.0003(4) 0.0022(4) C17 0.0230(5) 0.0205(5) 0.0404(6) -0.0082(4) 0.0028(4) -0.0002(4) C18 0.0211(5) 0.0206(5) 0.0364(6) 0.0024(4) 0.0055(4) -0.0002(4) C19 0.0181(5) 0.0227(5) 0.0232(5) -0.0009(4) 0.0028(4) 0.0009(4) C20 0.0181(5) 0.0215(5) 0.0236(5) -0.0059(4) -0.0042(4) 0.0018(4) C21 0.0215(5) 0.0305(6) 0.0271(5) -0.0049(4) -0.0007(4) 0.0018(4) C22 0.0273(6) 0.0401(7) 0.0298(6) -0.0131(5) -0.0022(4) 0.0098(5) C23 0.0298(6) 0.0268(6) 0.0433(7) -0.0149(5) -0.0106(5) 0.0088(5) C24 0.0316(6) 0.0221(6) 0.0470(7) -0.0038(5) -0.0026(5) 0.0011(5) C25 0.0281(6) 0.0234(5) 0.0335(6) -0.0026(4) 0.0027(4) 0.0017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3804(12) . ? N1 C20 1.4391(12) . ? N1 C11 1.4865(12) . ? C1 C2 1.3642(14) . ? C1 C14 1.4930(13) . ? C2 C3 1.4203(14) . ? C2 H2 0.971(14) . ? C3 C4 1.2041(15) . ? C4 C5 1.4332(14) . ? C5 C6 1.4011(15) . ? C5 C10 1.4009(15) . ? C6 C7 1.3873(16) . ? C6 H6 0.983(15) . ? C7 C8 1.3870(17) . ? C7 H7 0.982(16) . ? C8 C9 1.3842(17) . ? C8 H8 0.984(14) . ? C9 C10 1.3874(15) . ? C9 H9 0.976(15) . ? C10 H10 0.987(14) . ? C11 C12 1.5168(14) . ? C11 C13 1.5247(15) . ? C11 H11 0.983(13) . ? C12 H12C 0.998(15) . ? C12 H12B 0.986(15) . ? C12 H12A 1.000(16) . ? C13 H13C 1.007(15) . ? C13 H13B 1.001(16) . ? C13 H13A 1.008(15) . ? C14 C19 1.3940(14) . ? C14 C15 1.3957(14) . ? C15 C16 1.3889(15) . ? C15 H15 0.987(14) . ? C16 C17 1.3849(17) . ? C16 H16 0.988(14) . ? C17 C18 1.3895(16) . ? C17 H17 0.973(14) . ? C18 C19 1.3904(15) . ? C18 H18 0.991(14) . ? C19 H19 0.970(13) . ? C20 C25 1.3894(16) . ? C20 C21 1.3909(15) . ? C21 C22 1.3930(16) . ? C21 H21 0.955(15) . ? C22 C23 1.3843(19) . ? C22 H22 0.981(15) . ? C23 C24 1.3810(19) . ? C23 H23 0.974(15) . ? C24 C25 1.3927(16) . ? C24 H24 0.991(16) . ? C25 H25 0.980(14) . ? 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 C20 117.65(8) . . ? C1 N1 C11 120.43(8) . . ? C20 N1 C11 119.07(8) . . ? C2 C1 N1 123.49(9) . . ? C2 C1 C14 118.83(9) . . ? N1 C1 C14 117.54(8) . . ? C1 C2 C3 121.23(9) . . ? C1 C2 H2 119.8(8) . . ? C3 C2 H2 118.6(8) . . ? C4 C3 C2 176.94(11) . . ? C3 C4 C5 174.26(11) . . ? C6 C5 C10 118.71(10) . . ? C6 C5 C4 119.54(9) . . ? C10 C5 C4 121.75(10) . . ? C7 C6 C5 120.32(11) . . ? C7 C6 H6 120.7(8) . . ? C5 C6 H6 119.0(8) . . ? C8 C7 C6 120.39(11) . . ? C8 C7 H7 120.7(9) . . ? C6 C7 H7 118.9(9) . . ? C9 C8 C7 119.75(10) . . ? C9 C8 H8 120.1(8) . . ? C7 C8 H8 120.1(8) . . ? C8 C9 C10 120.40(11) . . ? C8 C9 H9 120.6(9) . . ? C10 C9 H9 119.0(9) . . ? C9 C10 C5 120.39(10) . . ? C9 C10 H10 121.0(8) . . ? C5 C10 H10 118.7(8) . . ? N1 C11 C12 110.88(8) . . ? N1 C11 C13 112.47(8) . . ? C12 C11 C13 112.10(9) . . ? N1 C11 H11 104.8(7) . . ? C12 C11 H11 107.8(7) . . ? C13 C11 H11 108.4(7) . . ? C11 C12 H12C 109.3(8) . . ? C11 C12 H12B 111.0(9) . . ? H12C C12 H12B 108.0(12) . . ? C11 C12 H12A 111.0(9) . . ? H12C C12 H12A 108.8(12) . . ? H12B C12 H12A 108.5(12) . . ? C11 C13 H13C 109.5(8) . . ? C11 C13 H13B 110.8(9) . . ? H13C C13 H13B 108.0(12) . . ? C11 C13 H13A 110.7(9) . . ? H13C C13 H13A 109.2(12) . . ? H13B C13 H13A 108.7(12) . . ? C19 C14 C15 119.23(9) . . ? C19 C14 C1 120.67(9) . . ? C15 C14 C1 119.93(9) . . ? C16 C15 C14 120.42(10) . . ? C16 C15 H15 120.5(8) . . ? C14 C15 H15 119.1(8) . . ? C15 C16 C17 120.07(10) . . ? C15 C16 H16 119.1(8) . . ? C17 C16 H16 120.8(8) . . ? C16 C17 C18 119.91(10) . . ? C16 C17 H17 120.2(8) . . ? C18 C17 H17 119.9(8) . . ? C19 C18 C17 120.21(10) . . ? C19 C18 H18 119.3(8) . . ? C17 C18 H18 120.5(8) . . ? C18 C19 C14 120.14(10) . . ? C18 C19 H19 120.7(8) . . ? C14 C19 H19 119.1(8) . . ? C25 C20 C21 119.75(10) . . ? C25 C20 N1 121.86(9) . . ? C21 C20 N1 118.36(10) . . ? C20 C21 C22 119.88(11) . . ? C20 C21 H21 119.7(8) . . ? C22 C21 H21 120.5(8) . . ? C23 C22 C21 120.25(11) . . ? C23 C22 H22 121.6(9) . . ? C21 C22 H22 118.2(9) . . ? C24 C23 C22 119.85(11) . . ? C24 C23 H23 119.9(9) . . ? C22 C23 H23 120.2(9) . . ? C23 C24 C25 120.38(12) . . ? C23 C24 H24 119.8(9) . . ? C25 C24 H24 119.8(9) . . ? C20 C25 C24 119.89(11) . . ? C20 C25 H25 120.1(9) . . ? C24 C25 H25 120.0(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.257 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.033 data_FO4297 _database_code_depnum_ccdc_archive 'CCDC 873553' #TrackingRef 'chemcom.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H31 N' _chemical_formula_sum 'C41 H31 N' _chemical_formula_weight 537.67 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0932(3) _cell_length_b 11.9758(3) _cell_length_c 13.0546(3) _cell_angle_alpha 78.709(2) _cell_angle_beta 71.546(2) _cell_angle_gamma 89.447(1) _cell_volume 1465.53(7) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 9330 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.52 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9330 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.52 _reflns_number_total 6589 _reflns_number_gt 5588 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0332P)^2^+1.3917P] 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 6589 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1410 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.67881(15) 0.13264(12) 0.21358(12) 0.0213(3) Uani 1 1 d . . . C1 C 0.71833(17) 0.22416(14) 0.11997(13) 0.0199(3) Uani 1 1 d . . . C2 C 0.67851(18) 0.33348(14) 0.13098(13) 0.0200(3) Uani 1 1 d . . . C3 C 0.72430(17) 0.42727(14) 0.03877(14) 0.0193(3) Uani 1 1 d . . . C4 C 0.80147(17) 0.40705(14) -0.06436(14) 0.0198(3) Uani 1 1 d . . . C5 C 0.84330(17) 0.29470(14) -0.07751(13) 0.0195(3) Uani 1 1 d . . . C6 C 0.80115(17) 0.20294(14) 0.01530(14) 0.0194(3) Uani 1 1 d . . . C7 C 0.84305(18) 0.09202(15) 0.00135(14) 0.0224(3) Uani 1 1 d . . . H7A H 0.8143 0.0296 0.0624 0.027 Uiso 1 1 calc R . . C8 C 0.92471(19) 0.07406(15) -0.09965(15) 0.0236(4) Uani 1 1 d . . . H8A H 0.9515 -0.0008 -0.1080 0.028 Uiso 1 1 calc R . . C9 C 0.96908(19) 0.16537(16) -0.19101(14) 0.0244(4) Uani 1 1 d . . . H9A H 1.0274 0.1522 -0.2601 0.029 Uiso 1 1 calc R . . C10 C 0.92851(18) 0.27311(15) -0.18066(14) 0.0230(4) Uani 1 1 d . . . H10A H 0.9576 0.3341 -0.2431 0.028 Uiso 1 1 calc R . . C11 C 0.83103(18) 0.49817(14) -0.15898(14) 0.0214(3) Uani 1 1 d . . . C12 C 0.84499(18) 0.57360(15) -0.23775(14) 0.0229(4) Uani 1 1 d . . . C13 C 0.86409(18) 0.66909(15) -0.32743(14) 0.0224(3) Uani 1 1 d . . . C14 C 0.9620(2) 0.66866(17) -0.43056(15) 0.0287(4) Uani 1 1 d . . . H14A H 1.0112 0.6022 -0.4437 0.034 Uiso 1 1 calc R . . C15 C 0.9873(2) 0.76518(19) -0.51390(16) 0.0349(5) Uani 1 1 d . . . H15A H 1.0557 0.7652 -0.5834 0.042 Uiso 1 1 calc R . . C16 C 0.9133(2) 0.86172(17) -0.49627(17) 0.0355(5) Uani 1 1 d . . . H16A H 0.9318 0.9280 -0.5533 0.043 Uiso 1 1 calc R . . C17 C 0.8123(2) 0.86148(17) -0.39530(17) 0.0334(4) Uani 1 1 d . . . H17A H 0.7598 0.9268 -0.3839 0.040 Uiso 1 1 calc R . . C18 C 0.7880(2) 0.76596(16) -0.31103(15) 0.0273(4) Uani 1 1 d . . . H18A H 0.7193 0.7663 -0.2418 0.033 Uiso 1 1 calc R . . C19 C 0.69338(18) 0.54622(14) 0.05332(13) 0.0208(3) Uani 1 1 d . . . C20 C 0.80423(19) 0.62422(15) 0.03637(15) 0.0253(4) Uani 1 1 d . . . H20A H 0.8977 0.6011 0.0156 0.030 Uiso 1 1 calc R . . C21 C 0.7781(2) 0.73572(15) 0.04987(16) 0.0286(4) Uani 1 1 d . . . H21A H 0.8536 0.7881 0.0395 0.034 Uiso 1 1 calc R . . C22 C 0.6424(2) 0.77033(16) 0.07839(16) 0.0294(4) Uani 1 1 d . . . H22A H 0.6249 0.8468 0.0864 0.035 Uiso 1 1 calc R . . C23 C 0.5321(2) 0.69350(16) 0.09529(16) 0.0278(4) Uani 1 1 d . . . H23A H 0.4390 0.7175 0.1148 0.033 Uiso 1 1 calc R . . C24 C 0.55694(19) 0.58146(15) 0.08377(15) 0.0241(4) Uani 1 1 d . . . H24A H 0.4807 0.5289 0.0967 0.029 Uiso 1 1 calc R . . C25 C 0.58894(18) 0.35339(14) 0.23469(14) 0.0216(3) Uani 1 1 d . . . C26 C 0.50892(18) 0.37339(15) 0.31821(14) 0.0228(4) Uani 1 1 d . . . C27 C 0.41775(18) 0.40059(15) 0.41802(14) 0.0224(3) Uani 1 1 d . . . C28 C 0.37908(19) 0.51293(17) 0.41942(16) 0.0281(4) Uani 1 1 d . . . H28A H 0.4090 0.5700 0.3538 0.034 Uiso 1 1 calc R . . C29 C 0.2963(2) 0.54017(19) 0.51788(18) 0.0351(5) Uani 1 1 d . . . H29A H 0.2699 0.6164 0.5192 0.042 Uiso 1 1 calc R . . C30 C 0.2521(2) 0.4577(2) 0.61383(18) 0.0391(5) Uani 1 1 d . . . H30A H 0.1961 0.4774 0.6807 0.047 Uiso 1 1 calc R . . C31 C 0.2896(2) 0.3466(2) 0.61219(17) 0.0372(5) Uani 1 1 d . . . H31A H 0.2590 0.2899 0.6780 0.045 Uiso 1 1 calc R . . C32 C 0.37179(19) 0.31742(17) 0.51459(15) 0.0285(4) Uani 1 1 d . . . H32A H 0.3967 0.2408 0.5137 0.034 Uiso 1 1 calc R . . C33 C 0.7678(2) 0.10940(15) 0.28554(14) 0.0244(4) Uani 1 1 d . . . H33A H 0.7952 0.0287 0.2880 0.029 Uiso 1 1 calc R . . C34 C 0.6880(2) 0.12116(17) 0.40382(15) 0.0316(4) Uani 1 1 d . . . H34A H 0.5980 0.0773 0.4296 0.047 Uiso 1 1 calc R . . H34B H 0.6718 0.2017 0.4055 0.047 Uiso 1 1 calc R . . H34C H 0.7432 0.0920 0.4520 0.047 Uiso 1 1 calc R . . C35 C 0.9011(2) 0.18551(17) 0.24156(17) 0.0321(4) Uani 1 1 d . . . H35A H 0.9510 0.1788 0.1655 0.048 Uiso 1 1 calc R . . H35B H 0.9607 0.1620 0.2875 0.048 Uiso 1 1 calc R . . H35C H 0.8777 0.2649 0.2433 0.048 Uiso 1 1 calc R . . C36 C 0.57276(18) 0.05357(14) 0.22343(14) 0.0218(3) Uani 1 1 d . . . C37 C 0.5460(2) -0.05003(15) 0.30021(15) 0.0255(4) Uani 1 1 d . . . H37A H 0.6023 -0.0685 0.3466 0.031 Uiso 1 1 calc R . . C38 C 0.4377(2) -0.12593(16) 0.30908(16) 0.0304(4) Uani 1 1 d . . . H38A H 0.4210 -0.1957 0.3617 0.037 Uiso 1 1 calc R . . C39 C 0.3541(2) -0.10173(17) 0.24286(17) 0.0316(4) Uani 1 1 d . . . H39A H 0.2796 -0.1537 0.2500 0.038 Uiso 1 1 calc R . . C40 C 0.3807(2) -0.00027(17) 0.16576(16) 0.0303(4) Uani 1 1 d . . . H40A H 0.3247 0.0168 0.1189 0.036 Uiso 1 1 calc R . . C41 C 0.48770(19) 0.07669(16) 0.15585(15) 0.0257(4) Uani 1 1 d . . . H41A H 0.5038 0.1460 0.1027 0.031 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 0.0256(7) 0.0174(7) 0.0203(7) -0.0035(5) -0.0068(6) -0.0010(6) C1 0.0209(8) 0.0189(8) 0.0196(8) -0.0052(6) -0.0056(6) 0.0005(6) C2 0.0213(8) 0.0186(8) 0.0191(8) -0.0049(6) -0.0047(6) 0.0001(6) C3 0.0203(8) 0.0165(8) 0.0219(8) -0.0055(6) -0.0070(6) 0.0017(6) C4 0.0187(8) 0.0188(8) 0.0207(8) -0.0043(6) -0.0046(6) -0.0003(6) C5 0.0192(8) 0.0195(8) 0.0204(8) -0.0061(6) -0.0059(6) 0.0020(6) C6 0.0197(8) 0.0183(8) 0.0208(8) -0.0062(6) -0.0059(6) 0.0021(6) C7 0.0238(9) 0.0195(8) 0.0244(8) -0.0059(7) -0.0076(7) 0.0029(7) C8 0.0258(9) 0.0205(8) 0.0285(9) -0.0112(7) -0.0108(7) 0.0068(7) C9 0.0237(9) 0.0295(9) 0.0221(8) -0.0129(7) -0.0060(7) 0.0067(7) C10 0.0240(9) 0.0249(9) 0.0190(8) -0.0055(7) -0.0049(7) 0.0022(7) C11 0.0217(8) 0.0204(8) 0.0207(8) -0.0076(7) -0.0028(6) 0.0015(6) C12 0.0229(9) 0.0235(9) 0.0220(8) -0.0076(7) -0.0049(7) 0.0006(7) C13 0.0243(9) 0.0213(8) 0.0227(8) -0.0041(7) -0.0094(7) -0.0021(7) C14 0.0305(10) 0.0311(10) 0.0238(9) -0.0058(7) -0.0074(7) 0.0028(8) C15 0.0371(11) 0.0426(12) 0.0207(9) -0.0012(8) -0.0065(8) -0.0016(9) C16 0.0503(13) 0.0273(10) 0.0280(10) 0.0033(8) -0.0162(9) -0.0049(9) C17 0.0499(12) 0.0227(9) 0.0327(10) -0.0067(8) -0.0198(9) 0.0050(8) C18 0.0337(10) 0.0253(9) 0.0239(9) -0.0071(7) -0.0095(7) 0.0021(7) C19 0.0271(9) 0.0172(8) 0.0177(8) -0.0049(6) -0.0057(7) 0.0009(6) C20 0.0250(9) 0.0232(9) 0.0265(9) -0.0069(7) -0.0055(7) 0.0007(7) C21 0.0345(10) 0.0207(9) 0.0294(9) -0.0065(7) -0.0077(8) -0.0053(7) C22 0.0414(11) 0.0193(8) 0.0294(9) -0.0101(7) -0.0109(8) 0.0041(8) C23 0.0301(10) 0.0241(9) 0.0314(10) -0.0104(7) -0.0103(8) 0.0078(7) C24 0.0258(9) 0.0217(8) 0.0261(9) -0.0085(7) -0.0082(7) 0.0024(7) C25 0.0244(9) 0.0181(8) 0.0219(8) -0.0046(6) -0.0066(7) 0.0019(6) C26 0.0238(9) 0.0213(8) 0.0228(8) -0.0050(7) -0.0066(7) 0.0017(7) C27 0.0183(8) 0.0277(9) 0.0217(8) -0.0103(7) -0.0039(6) 0.0011(7) C28 0.0251(9) 0.0299(10) 0.0304(9) -0.0118(8) -0.0069(7) 0.0021(7) C29 0.0251(10) 0.0380(11) 0.0446(12) -0.0251(9) -0.0045(8) 0.0021(8) C30 0.0264(10) 0.0560(14) 0.0345(11) -0.0292(10) 0.0028(8) -0.0038(9) C31 0.0312(11) 0.0515(13) 0.0250(10) -0.0101(9) -0.0019(8) -0.0075(9) C32 0.0252(9) 0.0325(10) 0.0259(9) -0.0075(8) -0.0047(7) -0.0008(7) C33 0.0321(10) 0.0211(8) 0.0233(8) -0.0068(7) -0.0120(7) 0.0041(7) C34 0.0435(12) 0.0316(10) 0.0229(9) -0.0089(8) -0.0132(8) 0.0050(8) C35 0.0330(10) 0.0322(10) 0.0349(10) -0.0059(8) -0.0165(9) -0.0004(8) C36 0.0236(8) 0.0200(8) 0.0208(8) -0.0082(6) -0.0033(7) 0.0008(7) C37 0.0316(10) 0.0223(8) 0.0221(8) -0.0064(7) -0.0069(7) -0.0001(7) C38 0.0369(11) 0.0224(9) 0.0271(9) -0.0062(7) -0.0028(8) -0.0041(8) C39 0.0273(10) 0.0302(10) 0.0353(10) -0.0139(8) -0.0025(8) -0.0061(8) C40 0.0265(9) 0.0351(10) 0.0326(10) -0.0140(8) -0.0100(8) 0.0012(8) C41 0.0269(9) 0.0235(9) 0.0261(9) -0.0070(7) -0.0064(7) -0.0001(7) _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 C36 1.394(2) . ? N1 C1 1.424(2) . ? N1 C33 1.482(2) . ? C1 C2 1.387(2) . ? C1 C6 1.428(2) . ? C2 C3 1.433(2) . ? C2 C25 1.433(2) . ? C3 C4 1.392(2) . ? C3 C19 1.491(2) . ? C4 C5 1.432(2) . ? C4 C11 1.432(2) . ? C5 C6 1.421(2) . ? C5 C10 1.421(2) . ? C6 C7 1.418(2) . ? C7 C8 1.372(2) . ? C7 H7A 0.9500 . ? C8 C9 1.407(3) . ? C8 H8A 0.9500 . ? C9 C10 1.369(2) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 C12 1.200(2) . ? C12 C13 1.433(2) . ? C13 C14 1.396(3) . ? C13 C18 1.399(3) . ? C14 C15 1.386(3) . ? C14 H14A 0.9500 . ? C15 C16 1.388(3) . ? C15 H15A 0.9500 . ? C16 C17 1.387(3) . ? C16 H16A 0.9500 . ? C17 C18 1.386(3) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 C24 1.393(2) . ? C19 C20 1.398(2) . ? C20 C21 1.393(3) . ? C20 H20A 0.9500 . ? C21 C22 1.383(3) . ? C21 H21A 0.9500 . ? C22 C23 1.386(3) . ? C22 H22A 0.9500 . ? C23 C24 1.391(2) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C26 1.200(2) . ? C26 C27 1.432(2) . ? C27 C32 1.394(3) . ? C27 C28 1.399(3) . ? C28 C29 1.391(3) . ? C28 H28A 0.9500 . ? C29 C30 1.383(3) . ? C29 H29A 0.9500 . ? C30 C31 1.383(3) . ? C30 H30A 0.9500 . ? C31 C32 1.390(3) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C33 C35 1.516(3) . ? C33 C34 1.532(3) . ? C33 H33A 1.0000 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C37 1.402(2) . ? C36 C41 1.404(2) . ? C37 C38 1.390(3) . ? C37 H37A 0.9500 . ? C38 C39 1.380(3) . ? C38 H38A 0.9500 . ? C39 C40 1.385(3) . ? C39 H39A 0.9500 . ? C40 C41 1.385(3) . ? C40 H40A 0.9500 . ? C41 H41A 0.9500 . ? 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 C36 N1 C1 118.66(14) . . ? C36 N1 C33 120.42(14) . . ? C1 N1 C33 119.74(14) . . ? C2 C1 N1 120.11(15) . . ? C2 C1 C6 120.29(15) . . ? N1 C1 C6 119.59(15) . . ? C1 C2 C3 120.57(15) . . ? C1 C2 C25 120.14(15) . . ? C3 C2 C25 119.28(15) . . ? C4 C3 C2 119.53(15) . . ? C4 C3 C19 119.98(15) . . ? C2 C3 C19 120.47(15) . . ? C3 C4 C5 120.61(15) . . ? C3 C4 C11 119.37(15) . . ? C5 C4 C11 119.89(15) . . ? C6 C5 C10 119.11(15) . . ? C6 C5 C4 119.27(15) . . ? C10 C5 C4 121.61(15) . . ? C7 C6 C5 118.81(15) . . ? C7 C6 C1 121.61(15) . . ? C5 C6 C1 119.59(15) . . ? C8 C7 C6 120.55(16) . . ? C8 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C7 C8 C9 120.64(16) . . ? C7 C8 H8A 119.7 . . ? C9 C8 H8A 119.7 . . ? C10 C9 C8 120.21(16) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C9 C10 C5 120.66(16) . . ? C9 C10 H10A 119.7 . . ? C5 C10 H10A 119.7 . . ? C12 C11 C4 174.86(19) . . ? C11 C12 C13 175.91(18) . . ? C14 C13 C18 119.21(16) . . ? C14 C13 C12 120.77(16) . . ? C18 C13 C12 119.97(16) . . ? C15 C14 C13 120.08(18) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C16 120.29(19) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C17 C16 C15 119.99(18) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C18 C17 C16 120.01(19) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C17 C18 C13 120.35(18) . . ? C17 C18 H18A 119.8 . . ? C13 C18 H18A 119.8 . . ? C24 C19 C20 119.21(16) . . ? C24 C19 C3 121.68(15) . . ? C20 C19 C3 119.11(16) . . ? C21 C20 C19 120.23(17) . . ? C21 C20 H20A 119.9 . . ? C19 C20 H20A 119.9 . . ? C22 C21 C20 120.09(17) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C23 119.98(17) . . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C22 C23 C24 120.34(18) . . ? C22 C23 H23A 119.8 . . ? C24 C23 H23A 119.8 . . ? C23 C24 C19 120.13(17) . . ? C23 C24 H24A 119.9 . . ? C19 C24 H24A 119.9 . . ? C26 C25 C2 176.09(18) . . ? C25 C26 C27 177.60(19) . . ? C32 C27 C28 119.75(17) . . ? C32 C27 C26 120.72(16) . . ? C28 C27 C26 119.47(16) . . ? C29 C28 C27 119.30(19) . . ? C29 C28 H28A 120.4 . . ? C27 C28 H28A 120.4 . . ? C30 C29 C28 120.83(19) . . ? C30 C29 H29A 119.6 . . ? C28 C29 H29A 119.6 . . ? C29 C30 C31 119.83(18) . . ? C29 C30 H30A 120.1 . . ? C31 C30 H30A 120.1 . . ? C30 C31 C32 120.3(2) . . ? C30 C31 H31A 119.9 . . ? C32 C31 H31A 119.9 . . ? C31 C32 C27 120.01(19) . . ? C31 C32 H32A 120.0 . . ? C27 C32 H32A 120.0 . . ? N1 C33 C35 112.39(15) . . ? N1 C33 C34 111.51(15) . . ? C35 C33 C34 109.70(16) . . ? N1 C33 H33A 107.7 . . ? C35 C33 H33A 107.7 . . ? C34 C33 H33A 107.7 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N1 C36 C37 122.18(16) . . ? N1 C36 C41 120.14(15) . . ? C37 C36 C41 117.68(16) . . ? C38 C37 C36 120.60(17) . . ? C38 C37 H37A 119.7 . . ? C36 C37 H37A 119.7 . . ? C39 C38 C37 121.15(18) . . ? C39 C38 H38A 119.4 . . ? C37 C38 H38A 119.4 . . ? C38 C39 C40 118.75(18) . . ? C38 C39 H39A 120.6 . . ? C40 C39 H39A 120.6 . . ? C41 C40 C39 121.01(18) . . ? C41 C40 H40A 119.5 . . ? C39 C40 H40A 119.5 . . ? C40 C41 C36 120.80(17) . . ? C40 C41 H41A 119.6 . . ? C36 C41 H41A 119.6 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.382 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.050