# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1a _database_code_depnum_ccdc_archive 'CCDC 899423' #TrackingRef '1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H20 N2' _chemical_formula_sum 'C30 H20 N2' _chemical_formula_weight 408.48 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.194(2) _cell_length_b 16.337(5) _cell_length_c 31.464(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4211.9(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 545 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 19.75 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method none _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6263 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20921 _diffrn_reflns_av_R_equivalents 0.1325 _diffrn_reflns_av_sigmaI/netI 0.0927 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3713 _reflns_number_gt 2072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0621P)^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 SHELXL _refine_ls_extinction_coef 0.0045(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3713 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1234 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1431 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.6425(3) 0.32245(15) 0.07192(7) 0.0291(6) Uani 1 1 d . . . N2 N 0.1100(3) 0.46416(14) 0.15686(8) 0.0268(6) Uani 1 1 d . . . C1 C 0.7273(4) 0.25052(18) 0.08125(9) 0.0286(7) Uani 1 1 d . . . C2 C 0.6913(4) 0.19054(19) 0.11088(10) 0.0344(8) Uani 1 1 d . . . H2A H 0.5991 0.1950 0.1290 0.041 Uiso 1 1 calc R . . C3 C 0.7950(4) 0.1239(2) 0.11303(10) 0.0383(9) Uani 1 1 d . . . H3A H 0.7737 0.0817 0.1330 0.046 Uiso 1 1 calc R . . C4 C 0.9308(4) 0.1177(2) 0.08623(10) 0.0390(9) Uani 1 1 d . . . H4A H 1.0000 0.0712 0.0884 0.047 Uiso 1 1 calc R . . C5 C 0.9659(4) 0.17752(19) 0.05680(10) 0.0369(8) Uani 1 1 d . . . H5A H 1.0589 0.1730 0.0389 0.044 Uiso 1 1 calc R . . C6 C 0.8623(4) 0.24462(19) 0.05389(9) 0.0297(7) Uani 1 1 d . . . C7 C 0.8596(4) 0.31600(19) 0.02664(9) 0.0298(8) Uani 1 1 d . . . C8 C 0.9550(4) 0.3436(2) -0.00694(10) 0.0374(8) Uani 1 1 d . . . H8A H 1.0473 0.3130 -0.0159 0.045 Uiso 1 1 calc R . . C9 C 0.9146(4) 0.4157(2) -0.02724(10) 0.0430(9) Uani 1 1 d . . . H9A H 0.9779 0.4340 -0.0507 0.052 Uiso 1 1 calc R . . C10 C 0.7812(4) 0.4623(2) -0.01347(10) 0.0412(9) Uani 1 1 d . . . H10A H 0.7571 0.5125 -0.0273 0.049 Uiso 1 1 calc R . . C11 C 0.6837(4) 0.43674(19) 0.01988(10) 0.0357(8) Uani 1 1 d . . . H11A H 0.5935 0.4685 0.0292 0.043 Uiso 1 1 calc R . . C12 C 0.7228(4) 0.36281(18) 0.03916(9) 0.0292(7) Uani 1 1 d . . . C13 C 0.5048(4) 0.35456(17) 0.09418(9) 0.0269(7) Uani 1 1 d . . . C14 C 0.3485(4) 0.34331(19) 0.07892(10) 0.0358(8) Uani 1 1 d . . . H14A H 0.3308 0.3107 0.0544 0.043 Uiso 1 1 calc R . . C15 C 0.2169(4) 0.37966(18) 0.09948(9) 0.0310(8) Uani 1 1 d . . . H15A H 0.1094 0.3722 0.0889 0.037 Uiso 1 1 calc R . . C16 C 0.2430(4) 0.42663(16) 0.13536(9) 0.0245(7) Uani 1 1 d . . . C17 C 0.3991(4) 0.43569(18) 0.15139(9) 0.0297(7) Uani 1 1 d . . . H17A H 0.4162 0.4659 0.1768 0.036 Uiso 1 1 calc R . . C18 C 0.5305(4) 0.40089(17) 0.13047(9) 0.0290(7) Uani 1 1 d . . . H18A H 0.6380 0.4087 0.1410 0.035 Uiso 1 1 calc R . . C19 C -0.0160(3) 0.42200(17) 0.17759(9) 0.0245(7) Uani 1 1 d . . . C20 C -0.0594(3) 0.34004(17) 0.17466(9) 0.0270(7) Uani 1 1 d . . . H20A H -0.0050 0.3040 0.1557 0.032 Uiso 1 1 calc R . . C21 C -0.1846(4) 0.31293(19) 0.20033(10) 0.0331(8) Uani 1 1 d . . . H21A H -0.2161 0.2570 0.1991 0.040 Uiso 1 1 calc R . . C22 C -0.2663(4) 0.3657(2) 0.22811(9) 0.0354(8) Uani 1 1 d . . . H22A H -0.3512 0.3451 0.2457 0.042 Uiso 1 1 calc R . . C23 C -0.2249(4) 0.4472(2) 0.23019(9) 0.0337(8) Uani 1 1 d . . . H23A H -0.2822 0.4834 0.2485 0.040 Uiso 1 1 calc R . . C24 C -0.0977(4) 0.47579(18) 0.20500(9) 0.0262(7) Uani 1 1 d . . . C25 C -0.0183(4) 0.55494(17) 0.20114(9) 0.0268(7) Uani 1 1 d . . . C26 C -0.0407(4) 0.63029(19) 0.22083(10) 0.0339(8) Uani 1 1 d . . . H26A H -0.1249 0.6376 0.2412 0.041 Uiso 1 1 calc R . . C27 C 0.0618(4) 0.69437(19) 0.21016(11) 0.0388(9) Uani 1 1 d . . . H27A H 0.0480 0.7462 0.2234 0.047 Uiso 1 1 calc R . . C28 C 0.1848(4) 0.68364(19) 0.18021(11) 0.0389(9) Uani 1 1 d . . . H28A H 0.2526 0.7288 0.1732 0.047 Uiso 1 1 calc R . . C29 C 0.2115(4) 0.60995(17) 0.16046(10) 0.0335(8) Uani 1 1 d . . . H29A H 0.2956 0.6034 0.1400 0.040 Uiso 1 1 calc R . . C30 C 0.1098(4) 0.54513(17) 0.17185(9) 0.0267(7) Uani 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 0.0297(15) 0.0331(15) 0.0245(14) -0.0029(11) 0.0057(12) 0.0024(12) N2 0.0260(14) 0.0247(13) 0.0297(15) -0.0005(11) 0.0053(12) 0.0017(11) C1 0.0277(18) 0.0328(18) 0.0253(17) -0.0097(14) -0.0031(15) 0.0026(15) C2 0.036(2) 0.040(2) 0.0272(17) -0.0047(15) 0.0025(15) 0.0055(16) C3 0.045(2) 0.039(2) 0.0308(18) 0.0002(16) -0.0021(17) 0.0057(17) C4 0.042(2) 0.040(2) 0.035(2) -0.0097(16) -0.0073(17) 0.0120(17) C5 0.0313(19) 0.046(2) 0.0333(19) -0.0130(16) 0.0004(16) 0.0050(16) C6 0.0256(17) 0.0387(19) 0.0248(16) -0.0132(14) 0.0002(15) 0.0001(15) C7 0.0259(17) 0.0354(19) 0.0281(18) -0.0103(14) 0.0006(15) -0.0053(15) C8 0.036(2) 0.042(2) 0.0339(19) -0.0106(16) 0.0085(16) -0.0078(17) C9 0.046(2) 0.049(2) 0.035(2) -0.0083(17) 0.0111(18) -0.0135(19) C10 0.052(2) 0.0361(19) 0.0358(19) -0.0013(15) 0.0019(19) -0.0127(18) C11 0.039(2) 0.036(2) 0.0320(18) -0.0051(15) 0.0056(16) -0.0046(16) C12 0.0294(18) 0.0330(18) 0.0251(17) -0.0074(14) 0.0027(15) -0.0061(15) C13 0.0303(18) 0.0270(17) 0.0234(16) 0.0001(13) 0.0062(15) 0.0040(14) C14 0.035(2) 0.044(2) 0.0289(18) -0.0105(15) 0.0001(16) -0.0017(17) C15 0.0256(18) 0.0394(19) 0.0279(17) -0.0051(14) -0.0010(15) -0.0008(15) C16 0.0259(17) 0.0248(16) 0.0230(15) 0.0016(13) 0.0037(15) 0.0023(13) C17 0.0310(18) 0.0322(18) 0.0260(17) -0.0032(14) 0.0018(15) 0.0007(15) C18 0.0257(18) 0.0361(18) 0.0251(17) -0.0003(14) -0.0009(15) 0.0026(15) C19 0.0231(16) 0.0269(17) 0.0235(16) 0.0038(13) -0.0021(14) 0.0015(14) C20 0.0236(17) 0.0289(17) 0.0286(17) 0.0013(13) 0.0003(14) 0.0015(14) C21 0.0338(19) 0.0335(18) 0.0321(18) 0.0048(15) -0.0060(16) -0.0038(16) C22 0.0288(18) 0.051(2) 0.0266(17) 0.0051(15) 0.0032(15) -0.0070(16) C23 0.0285(19) 0.045(2) 0.0274(17) -0.0029(15) 0.0015(15) 0.0018(16) C24 0.0231(17) 0.0341(18) 0.0213(16) -0.0020(13) -0.0028(14) 0.0033(14) C25 0.0270(18) 0.0303(18) 0.0231(16) -0.0006(13) -0.0019(14) 0.0038(14) C26 0.0332(19) 0.0369(19) 0.0315(18) -0.0076(15) -0.0066(16) 0.0103(16) C27 0.040(2) 0.0296(19) 0.047(2) -0.0130(16) -0.0150(18) 0.0077(17) C28 0.036(2) 0.0292(18) 0.052(2) 0.0014(16) -0.0068(18) 0.0014(16) C29 0.0335(19) 0.0272(18) 0.0399(19) 0.0045(15) 0.0017(16) 0.0009(15) C30 0.0266(17) 0.0257(17) 0.0277(17) 0.0007(13) -0.0029(15) 0.0038(14) _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 C12 1.389(4) . ? N1 C1 1.396(4) . ? N1 C13 1.428(4) . ? N2 C19 1.402(3) . ? N2 C30 1.404(3) . ? N2 C16 1.422(3) . ? C1 C2 1.384(4) . ? C1 C6 1.405(4) . ? C2 C3 1.382(4) . ? C2 H2A 0.9500 . ? C3 C4 1.400(4) . ? C3 H3A 0.9500 . ? C4 C5 1.377(4) . ? C4 H4A 0.9500 . ? C5 C6 1.390(4) . ? C5 H5A 0.9500 . ? C6 C7 1.448(4) . ? C7 C8 1.389(4) . ? C7 C12 1.413(4) . ? C8 C9 1.381(5) . ? C8 H8A 0.9500 . ? C9 C10 1.400(5) . ? C9 H9A 0.9500 . ? C10 C11 1.383(4) . ? C10 H10A 0.9500 . ? C11 C12 1.389(4) . ? C11 H11A 0.9500 . ? C13 C14 1.380(4) . ? C13 C18 1.386(4) . ? C14 C15 1.391(4) . ? C14 H14A 0.9500 . ? C15 C16 1.382(4) . ? C15 H15A 0.9500 . ? C16 C17 1.383(4) . ? C17 C18 1.384(4) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 C20 1.389(4) . ? C19 C24 1.402(4) . ? C20 C21 1.378(4) . ? C20 H20A 0.9500 . ? C21 C22 1.399(4) . ? C21 H21A 0.9500 . ? C22 C23 1.376(4) . ? C22 H22A 0.9500 . ? C23 C24 1.390(4) . ? C23 H23A 0.9500 . ? C24 C25 1.453(4) . ? C25 C26 1.390(4) . ? C25 C30 1.405(4) . ? C26 C27 1.384(4) . ? C26 H26A 0.9500 . ? C27 C28 1.391(4) . ? C27 H27A 0.9500 . ? C28 C29 1.372(4) . ? C28 H28A 0.9500 . ? C29 C30 1.395(4) . ? C29 H29A 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 C12 N1 C1 108.7(2) . . ? C12 N1 C13 124.3(2) . . ? C1 N1 C13 126.8(2) . . ? C19 N2 C30 107.8(2) . . ? C19 N2 C16 125.0(2) . . ? C30 N2 C16 124.5(2) . . ? C2 C1 N1 129.1(3) . . ? C2 C1 C6 122.1(3) . . ? N1 C1 C6 108.7(3) . . ? C3 C2 C1 117.4(3) . . ? C3 C2 H2A 121.3 . . ? C1 C2 H2A 121.3 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 121.3(3) . . ? C5 C4 H4A 119.4 . . ? C3 C4 H4A 119.4 . . ? C4 C5 C6 118.5(3) . . ? C4 C5 H5A 120.8 . . ? C6 C5 H5A 120.8 . . ? C5 C6 C1 119.7(3) . . ? C5 C6 C7 133.2(3) . . ? C1 C6 C7 107.2(3) . . ? C8 C7 C12 118.9(3) . . ? C8 C7 C6 134.7(3) . . ? C12 C7 C6 106.4(3) . . ? C9 C8 C7 119.6(3) . . ? C9 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9A 119.8 . . ? C10 C9 H9A 119.8 . . ? C11 C10 C9 121.5(3) . . ? C11 C10 H10A 119.3 . . ? C9 C10 H10A 119.3 . . ? C10 C11 C12 117.4(3) . . ? C10 C11 H11A 121.3 . . ? C12 C11 H11A 121.3 . . ? N1 C12 C11 128.9(3) . . ? N1 C12 C7 109.0(3) . . ? C11 C12 C7 122.1(3) . . ? C14 C13 C18 120.0(3) . . ? C14 C13 N1 120.9(3) . . ? C18 C13 N1 119.0(3) . . ? C13 C14 C15 120.1(3) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C16 C15 C14 119.8(3) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C15 C16 C17 120.0(3) . . ? C15 C16 N2 120.6(3) . . ? C17 C16 N2 119.3(2) . . ? C16 C17 C18 120.1(3) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C17 C18 C13 119.9(3) . . ? C17 C18 H18A 120.1 . . ? C13 C18 H18A 120.1 . . ? C20 C19 C24 121.5(3) . . ? C20 C19 N2 129.2(3) . . ? C24 C19 N2 109.3(2) . . ? C21 C20 C19 117.5(3) . . ? C21 C20 H20A 121.3 . . ? C19 C20 H20A 121.3 . . ? C20 C21 C22 121.6(3) . . ? C20 C21 H21A 119.2 . . ? C22 C21 H21A 119.2 . . ? C23 C22 C21 120.5(3) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C22 C23 C24 118.9(3) . . ? C22 C23 H23A 120.6 . . ? C24 C23 H23A 120.6 . . ? C23 C24 C19 119.9(3) . . ? C23 C24 C25 133.0(3) . . ? C19 C24 C25 107.0(2) . . ? C26 C25 C30 119.5(3) . . ? C26 C25 C24 133.7(3) . . ? C30 C25 C24 106.7(2) . . ? C27 C26 C25 118.8(3) . . ? C27 C26 H26A 120.6 . . ? C25 C26 H26A 120.6 . . ? C26 C27 C28 120.6(3) . . ? C26 C27 H27A 119.7 . . ? C28 C27 H27A 119.7 . . ? C29 C28 C27 122.2(3) . . ? C29 C28 H28A 118.9 . . ? C27 C28 H28A 118.9 . . ? C28 C29 C30 117.0(3) . . ? C28 C29 H29A 121.5 . . ? C30 C29 H29A 121.5 . . ? C29 C30 N2 128.9(3) . . ? C29 C30 C25 121.9(3) . . ? N2 C30 C25 109.2(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.222 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.060 data_2b _database_code_depnum_ccdc_archive 'CCDC 899424' #TrackingRef '2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H56 N2' _chemical_formula_sum 'C52 H56 N2' _chemical_formula_weight 708.99 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 16.051(10) _cell_length_b 11.186(7) _cell_length_c 11.531(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.031(9) _cell_angle_gamma 90.00 _cell_volume 2065(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5906 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 29.92 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6282 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25801 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4746 _reflns_number_gt 3707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0914P)^2^+0.3473P] 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 4746 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1578 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.17112(7) 0.29529(10) 0.23075(11) 0.0225(3) Uani 1 1 d . A . C1 C 0.23463(9) 0.26685(12) 0.31338(12) 0.0212(3) Uani 1 1 d . . . C2 C 0.25317(9) 0.15894(13) 0.36793(13) 0.0247(3) Uani 1 1 d . . . H2A H 0.2210 0.0894 0.3494 0.030 Uiso 1 1 calc R . . C3 C 0.31994(9) 0.15556(13) 0.45004(13) 0.0241(3) Uani 1 1 d . . . H3A H 0.3330 0.0821 0.4884 0.029 Uiso 1 1 calc R . . C4 C 0.36952(9) 0.25613(13) 0.47937(12) 0.0215(3) Uani 1 1 d . . . C5 C 0.34922(9) 0.36362(12) 0.42324(12) 0.0213(3) Uani 1 1 d . . . H5A H 0.3815 0.4331 0.4418 0.026 Uiso 1 1 calc R . . C6 C 0.28214(8) 0.37017(12) 0.34037(12) 0.0197(3) Uani 1 1 d . . . C7 C 0.24612(8) 0.46535(12) 0.26867(12) 0.0202(3) Uani 1 1 d . . . C8 C 0.26381(9) 0.58683(12) 0.25780(12) 0.0204(3) Uani 1 1 d . . . H8A H 0.3092 0.6212 0.3034 0.025 Uiso 1 1 calc R . . C9 C 0.21564(9) 0.65751(12) 0.18104(12) 0.0220(3) Uani 1 1 d . . . C10 C 0.14983(9) 0.60283(13) 0.11317(13) 0.0254(3) Uani 1 1 d . . . H10A H 0.1171 0.6506 0.0592 0.030 Uiso 1 1 calc R . . C11 C 0.13071(9) 0.48283(13) 0.12158(13) 0.0254(3) Uani 1 1 d . . . H11A H 0.0861 0.4481 0.0746 0.030 Uiso 1 1 calc R . . C12 C 0.17921(9) 0.41517(12) 0.20124(12) 0.0211(3) Uani 1 1 d . . . C13 C 0.12068(9) 0.21122(12) 0.16523(13) 0.0225(3) Uani 1 1 d . . . C14 C 0.1386(8) 0.1798(12) 0.0639(11) 0.030(2) Uani 0.53(2) 1 d P A 1 H14A H 0.1860 0.2140 0.0317 0.036 Uiso 0.53(2) 1 calc PR A 1 C15 C 0.0889(8) 0.0933(14) -0.0035(13) 0.027(2) Uani 0.53(2) 1 d P A 1 H15A H 0.1050 0.0716 -0.0784 0.032 Uiso 0.53(2) 1 calc PR A 1 C14' C 0.1550(8) 0.1592(12) 0.0623(10) 0.0184(15) Uani 0.47(2) 1 d P A 2 H14B H 0.2094 0.1799 0.0417 0.022 Uiso 0.47(2) 1 calc PR A 2 C15' C 0.1090(8) 0.0835(15) -0.0010(14) 0.0195(16) Uani 0.47(2) 1 d P A 2 H15B H 0.1293 0.0521 -0.0701 0.023 Uiso 0.47(2) 1 calc PR A 2 C16 C 0.02455(8) 0.04567(12) 0.03426(12) 0.0219(3) Uani 1 1 d . . . C17 C 0.0029(5) 0.0749(9) 0.1510(8) 0.0261(13) Uani 0.53(2) 1 d P A 1 H17A H -0.0438 0.0380 0.1825 0.031 Uiso 0.53(2) 1 calc PR A 1 C18 C 0.0512(5) 0.1578(9) 0.2167(8) 0.0256(13) Uani 0.53(2) 1 d P A 1 H18A H 0.0382 0.1780 0.2934 0.031 Uiso 0.53(2) 1 calc PR A 1 C17' C -0.0051(5) 0.1081(10) 0.1214(10) 0.0280(15) Uani 0.47(2) 1 d P A 2 H17B H -0.0616 0.0964 0.1382 0.034 Uiso 0.47(2) 1 calc PR A 2 C18' C 0.0419(6) 0.1875(9) 0.1871(10) 0.0270(15) Uani 0.47(2) 1 d P A 2 H18B H 0.0180 0.2268 0.2498 0.032 Uiso 0.47(2) 1 calc PR A 2 C19 C 0.44513(9) 0.25010(14) 0.56669(13) 0.0249(3) Uani 1 1 d . . . C20 C 0.45450(10) 0.12820(15) 0.62623(15) 0.0323(4) Uani 1 1 d . . . H20A H 0.4617 0.0663 0.5676 0.048 Uiso 1 1 calc R . . H20B H 0.4044 0.1110 0.6672 0.048 Uiso 1 1 calc R . . H20C H 0.5034 0.1292 0.6820 0.048 Uiso 1 1 calc R . . C21 C 0.43806(11) 0.34505(16) 0.66108(15) 0.0357(4) Uani 1 1 d . . . H21A H 0.3883 0.3295 0.7033 0.054 Uiso 1 1 calc R . . H21B H 0.4336 0.4243 0.6250 0.054 Uiso 1 1 calc R . . H21C H 0.4878 0.3421 0.7154 0.054 Uiso 1 1 calc R . . C22 C 0.52380(10) 0.27399(17) 0.50268(15) 0.0352(4) Uani 1 1 d . . . H22A H 0.5290 0.2130 0.4426 0.053 Uiso 1 1 calc R . . H22B H 0.5729 0.2710 0.5581 0.053 Uiso 1 1 calc R . . H22C H 0.5199 0.3532 0.4664 0.053 Uiso 1 1 calc R . . C23 C 0.22848(9) 0.79246(13) 0.17066(12) 0.0237(3) Uani 1 1 d . . . C24 C 0.15307(10) 0.85626(13) 0.21593(14) 0.0293(3) Uani 1 1 d . . . H24A H 0.1605 0.9429 0.2096 0.044 Uiso 1 1 calc R . . H24B H 0.1481 0.8347 0.2975 0.044 Uiso 1 1 calc R . . H24C H 0.1023 0.8321 0.1697 0.044 Uiso 1 1 calc R . . C25 C 0.23681(11) 0.82674(15) 0.04364(14) 0.0320(4) Uani 1 1 d . . . H25A H 0.2471 0.9129 0.0383 0.048 Uiso 1 1 calc R . . H25B H 0.1851 0.8064 -0.0024 0.048 Uiso 1 1 calc R . . H25C H 0.2836 0.7829 0.0136 0.048 Uiso 1 1 calc R . . C26 C 0.30692(10) 0.83534(14) 0.24052(15) 0.0312(4) Uani 1 1 d . . . H26A H 0.3140 0.9213 0.2284 0.047 Uiso 1 1 calc R . . H26B H 0.3556 0.7925 0.2148 0.047 Uiso 1 1 calc R . . H26C H 0.3016 0.8197 0.3233 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 0.0232(6) 0.0159(6) 0.0273(6) -0.0027(5) -0.0058(5) -0.0014(5) C1 0.0196(7) 0.0198(7) 0.0238(7) -0.0043(5) -0.0004(5) 0.0002(5) C2 0.0252(7) 0.0169(7) 0.0317(8) -0.0033(6) -0.0004(6) -0.0012(5) C3 0.0249(7) 0.0177(7) 0.0295(8) 0.0009(5) 0.0011(6) 0.0033(5) C4 0.0195(7) 0.0222(7) 0.0229(7) -0.0013(5) 0.0019(5) 0.0015(5) C5 0.0213(7) 0.0195(7) 0.0230(7) -0.0020(5) 0.0006(5) -0.0020(5) C6 0.0199(6) 0.0175(6) 0.0216(6) -0.0026(5) 0.0018(5) 0.0004(5) C7 0.0200(7) 0.0199(7) 0.0207(7) -0.0028(5) 0.0009(5) -0.0001(5) C8 0.0207(7) 0.0190(7) 0.0213(7) -0.0018(5) -0.0008(5) -0.0024(5) C9 0.0238(7) 0.0194(7) 0.0228(7) -0.0006(5) 0.0006(6) -0.0011(5) C10 0.0265(7) 0.0231(7) 0.0256(7) 0.0009(6) -0.0041(6) 0.0014(6) C11 0.0258(7) 0.0240(7) 0.0253(7) -0.0036(6) -0.0059(6) -0.0011(6) C12 0.0232(7) 0.0173(7) 0.0228(7) -0.0033(5) 0.0015(5) -0.0014(5) C13 0.0214(7) 0.0168(6) 0.0283(7) -0.0041(5) -0.0049(6) -0.0007(5) C14 0.025(4) 0.026(4) 0.040(3) -0.009(3) 0.014(3) -0.012(3) C15 0.020(5) 0.041(4) 0.021(2) -0.009(2) 0.002(3) -0.012(4) C14' 0.018(3) 0.021(3) 0.016(2) -0.0056(19) 0.007(2) -0.002(2) C15' 0.009(4) 0.027(3) 0.023(3) -0.0012(18) 0.006(3) -0.007(3) C16 0.0187(7) 0.0186(7) 0.0278(7) -0.0034(6) -0.0027(6) 0.0005(5) C17 0.023(2) 0.027(3) 0.029(3) -0.008(2) 0.008(2) -0.009(2) C18 0.023(2) 0.030(3) 0.023(3) -0.008(2) 0.002(2) -0.005(2) C17' 0.019(2) 0.030(4) 0.036(4) -0.007(3) 0.006(2) -0.005(2) C18' 0.024(2) 0.028(4) 0.029(4) -0.010(2) 0.002(3) 0.003(2) C19 0.0236(7) 0.0265(7) 0.0241(7) 0.0021(6) -0.0006(6) 0.0019(6) C20 0.0296(8) 0.0334(9) 0.0329(8) 0.0067(7) -0.0034(7) 0.0029(7) C21 0.0411(10) 0.0357(9) 0.0287(8) -0.0048(7) -0.0082(7) 0.0036(7) C22 0.0227(8) 0.0487(11) 0.0338(9) 0.0092(7) -0.0015(6) -0.0011(7) C23 0.0262(7) 0.0189(7) 0.0257(7) 0.0022(5) -0.0007(6) -0.0008(5) C24 0.0332(8) 0.0216(7) 0.0331(8) -0.0002(6) 0.0032(7) 0.0019(6) C25 0.0382(9) 0.0286(8) 0.0294(8) 0.0057(6) 0.0040(7) -0.0012(7) C26 0.0345(9) 0.0200(7) 0.0382(9) 0.0037(6) -0.0052(7) -0.0053(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 1.3827(19) . ? N1 C12 1.392(2) . ? N1 C13 1.4229(18) . ? C1 C2 1.384(2) . ? C1 C6 1.407(2) . ? C2 C3 1.380(2) . ? C2 H2A 0.9500 . ? C3 C4 1.405(2) . ? C3 H3A 0.9500 . ? C4 C5 1.393(2) . ? C4 C19 1.523(2) . ? C5 C6 1.390(2) . ? C5 H5A 0.9500 . ? C6 C7 1.444(2) . ? C7 C8 1.396(2) . ? C7 C12 1.398(2) . ? C8 C9 1.382(2) . ? C8 H8A 0.9500 . ? C9 C10 1.409(2) . ? C9 C23 1.529(2) . ? C10 C11 1.382(2) . ? C10 H10A 0.9500 . ? C11 C12 1.386(2) . ? C11 H11A 0.9500 . ? C13 C14 1.272(13) . ? C13 C18' 1.334(9) . ? C13 C18 1.431(8) . ? C13 C14' 1.464(12) . ? C14 C15 1.45(2) . ? C14 H14A 0.9500 . ? C15 C16 1.266(14) . ? C15 H15A 0.9500 . ? C14' C15' 1.31(2) . ? C14' H14B 0.9500 . ? C15' C16 1.503(14) . ? C15' H15B 0.9500 . ? C16 C17' 1.338(9) . ? C16 C17 1.451(8) . ? C16 C16 1.484(3) 3 ? C17 C18 1.397(10) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C17' C18' 1.360(13) . ? C17' H17B 0.9500 . ? C18' H18B 0.9500 . ? C19 C20 1.529(2) . ? C19 C22 1.530(2) . ? C19 C21 1.531(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C26 1.524(2) . ? C23 C24 1.528(2) . ? C23 C25 1.529(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 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 C12 108.25(11) . . ? C1 N1 C13 125.33(12) . . ? C12 N1 C13 124.50(12) . . ? N1 C1 C2 129.68(13) . . ? N1 C1 C6 108.98(12) . . ? C2 C1 C6 121.33(14) . . ? C3 C2 C1 117.88(13) . . ? C3 C2 H2A 121.1 . . ? C1 C2 H2A 121.1 . . ? C2 C3 C4 122.86(14) . . ? C2 C3 H3A 118.6 . . ? C4 C3 H3A 118.6 . . ? C5 C4 C3 117.97(14) . . ? C5 C4 C19 119.66(13) . . ? C3 C4 C19 122.35(13) . . ? C6 C5 C4 120.61(13) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C1 119.35(13) . . ? C5 C6 C7 133.79(13) . . ? C1 C6 C7 106.86(13) . . ? C8 C7 C12 119.60(13) . . ? C8 C7 C6 133.92(13) . . ? C12 C7 C6 106.46(12) . . ? C9 C8 C7 120.42(13) . . ? C9 C8 H8A 119.8 . . ? C7 C8 H8A 119.8 . . ? C8 C9 C10 118.11(13) . . ? C8 C9 C23 122.85(13) . . ? C10 C9 C23 118.99(13) . . ? C11 C10 C9 122.96(14) . . ? C11 C10 H10A 118.5 . . ? C9 C10 H10A 118.5 . . ? C10 C11 C12 117.37(13) . . ? C10 C11 H11A 121.3 . . ? C12 C11 H11A 121.3 . . ? C11 C12 N1 129.07(13) . . ? C11 C12 C7 121.52(13) . . ? N1 C12 C7 109.39(12) . . ? C14 C13 C18' 113.4(7) . . ? C14 C13 N1 120.9(6) . . ? C18' C13 N1 122.9(4) . . ? C14 C13 C18 119.9(7) . . ? C18' C13 C18 20.1(3) . . ? N1 C13 C18 119.2(3) . . ? C14 C13 C14' 12.3(9) . . ? C18' C13 C14' 119.3(7) . . ? N1 C13 C14' 117.4(6) . . ? C18 C13 C14' 121.3(6) . . ? C13 C14 C15 121.8(10) . . ? C13 C14 H14A 119.1 . . ? C15 C14 H14A 119.1 . . ? C16 C15 C14 122.0(11) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C15' C14' C13 118.6(11) . . ? C15' C14' H14B 120.7 . . ? C13 C14' H14B 120.7 . . ? C14' C15' C16 121.0(12) . . ? C14' C15' H15B 119.5 . . ? C16 C15' H15B 119.5 . . ? C15 C16 C17' 112.3(7) . . ? C15 C16 C17 118.6(7) . . ? C17' C16 C17 20.7(3) . . ? C15 C16 C16 121.5(7) . 3 ? C17' C16 C16 123.8(4) . 3 ? C17 C16 C16 119.7(3) . 3 ? C15 C16 C15' 10.2(11) . . ? C17' C16 C15' 115.5(8) . . ? C17 C16 C15' 117.8(7) . . ? C16 C16 C15' 120.3(7) 3 . ? C18 C17 C16 119.5(6) . . ? C18 C17 H17A 120.2 . . ? C16 C17 H17A 120.2 . . ? C17 C18 C13 118.1(6) . . ? C17 C18 H18A 120.9 . . ? C13 C18 H18A 120.9 . . ? C16 C17' C18' 123.1(7) . . ? C16 C17' H17B 118.4 . . ? C18' C17' H17B 118.4 . . ? C13 C18' C17' 121.4(7) . . ? C13 C18' H18B 119.3 . . ? C17' C18' H18B 119.3 . . ? C4 C19 C20 112.64(13) . . ? C4 C19 C22 108.64(13) . . ? C20 C19 C22 108.29(13) . . ? C4 C19 C21 110.11(13) . . ? C20 C19 C21 108.02(14) . . ? C22 C19 C21 109.07(14) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C26 C23 C24 108.49(13) . . ? C26 C23 C25 107.63(13) . . ? C24 C23 C25 109.56(13) . . ? C26 C23 C9 112.34(12) . . ? C24 C23 C9 108.66(12) . . ? C25 C23 C9 110.11(12) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.306 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.055 data_3a _database_code_depnum_ccdc_archive 'CCDC 899425' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H28 N2' _chemical_formula_sum 'C40 H28 N2' _chemical_formula_weight 536.64 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 13.167(5) _cell_length_b 13.192(5) _cell_length_c 8.213(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.701(7) _cell_angle_gamma 90.00 _cell_volume 1366.4(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1462 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 22.68 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method none _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6273 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10716 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2398 _reflns_number_gt 1548 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0501P)^2^+0.2418P] 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 2398 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.75405(13) 0.21105(13) 0.3295(2) 0.0380(4) Uani 1 1 d . . . C1 C 0.65185(17) 0.22067(16) 0.2177(3) 0.0397(5) Uani 1 1 d . . . C2 C 0.60432(17) 0.30441(18) 0.1240(3) 0.0439(6) Uani 1 1 d . . . H2A H 0.6405 0.3673 0.1317 0.053 Uiso 1 1 calc R . . C3 C 0.50181(18) 0.2923(2) 0.0188(3) 0.0500(6) Uani 1 1 d . . . H3A H 0.4676 0.3482 -0.0478 0.060 Uiso 1 1 calc R . . C4 C 0.44786(19) 0.2016(2) 0.0077(3) 0.0545(7) Uani 1 1 d . . . H4A H 0.3771 0.1966 -0.0636 0.065 Uiso 1 1 calc R . . C5 C 0.49570(18) 0.1186(2) 0.0989(3) 0.0506(6) Uani 1 1 d . . . H5A H 0.4585 0.0562 0.0901 0.061 Uiso 1 1 calc R . . C6 C 0.59982(17) 0.12670(17) 0.2050(3) 0.0416(5) Uani 1 1 d . . . C7 C 0.67297(16) 0.05780(16) 0.3143(3) 0.0403(5) Uani 1 1 d . . . C8 C 0.66581(19) -0.04279(17) 0.3591(3) 0.0489(6) Uani 1 1 d . . . H8A H 0.6029 -0.0805 0.3105 0.059 Uiso 1 1 calc R . . C9 C 0.7513(2) -0.08720(17) 0.4750(3) 0.0507(6) Uani 1 1 d . . . H9A H 0.7466 -0.1560 0.5064 0.061 Uiso 1 1 calc R . . C10 C 0.84473(19) -0.03292(16) 0.5476(3) 0.0476(6) Uani 1 1 d . . . H10A H 0.9024 -0.0655 0.6269 0.057 Uiso 1 1 calc R . . C11 C 0.85428(18) 0.06721(15) 0.5055(3) 0.0413(5) Uani 1 1 d . . . H11A H 0.9174 0.1044 0.5546 0.050 Uiso 1 1 calc R . . C12 C 0.76754(17) 0.11156(15) 0.3882(3) 0.0376(5) Uani 1 1 d . . . C13 C 0.82682(16) 0.29236(16) 0.3845(3) 0.0368(5) Uani 1 1 d . . . C14 C 0.79354(17) 0.38060(16) 0.4441(3) 0.0436(6) Uani 1 1 d . . . H14A H 0.7235 0.3847 0.4540 0.052 Uiso 1 1 calc R . . C15 C 0.86070(17) 0.46298(15) 0.4896(3) 0.0410(5) Uani 1 1 d . . . C16 C 0.96422(15) 0.45608(14) 0.4782(2) 0.0349(5) Uani 1 1 d . . . C17 C 0.99898(17) 0.36605(16) 0.4226(3) 0.0511(6) Uani 1 1 d . . . C18 C 0.92939(16) 0.28491(17) 0.3746(3) 0.0487(6) Uani 1 1 d . . . H18A H 0.9526 0.2241 0.3346 0.058 Uiso 1 1 calc R . . C19 C 0.8416(5) 0.5514(5) 0.5873(8) 0.0370(14) Uani 0.50 1 d P . 1 H19A H 0.8741 0.5388 0.7102 0.044 Uiso 0.50 1 calc PR . 1 H19B H 0.7643 0.5600 0.5678 0.044 Uiso 0.50 1 calc PR . 1 C20 C 1.1126(4) 0.3515(3) 0.4631(8) 0.0422(12) Uani 0.50 1 d P . 1 H20C H 1.1288 0.2931 0.3993 0.051 Uiso 0.50 1 calc PR . 1 H20D H 1.1432 0.3385 0.5862 0.051 Uiso 0.50 1 calc PR . 1 C19' C 0.8093(5) 0.5692(5) 0.5063(7) 0.0376(15) Uani 0.50 1 d P . 2 H19C H 0.7913 0.6060 0.3967 0.045 Uiso 0.50 1 calc PR . 2 H19D H 0.7440 0.5605 0.5416 0.045 Uiso 0.50 1 calc PR . 2 C20' C 1.1070(3) 0.3734(4) 0.3586(6) 0.0353(11) Uani 0.50 1 d P . 2 H20A H 1.1328 0.3046 0.3434 0.042 Uiso 0.50 1 calc PR . 2 H20B H 1.0911 0.4096 0.2485 0.042 Uiso 0.50 1 calc PR . 2 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 0.0381(10) 0.0382(10) 0.0404(11) 0.0036(8) 0.0152(9) -0.0009(8) C1 0.0411(13) 0.0503(14) 0.0344(12) -0.0026(11) 0.0214(11) 0.0009(11) C2 0.0429(14) 0.0583(15) 0.0375(12) 0.0029(11) 0.0227(11) 0.0050(11) C3 0.0489(15) 0.0724(18) 0.0350(13) 0.0026(12) 0.0224(12) 0.0136(13) C4 0.0470(14) 0.0778(19) 0.0416(14) -0.0073(14) 0.0171(12) 0.0084(15) C5 0.0471(15) 0.0634(16) 0.0468(14) -0.0177(13) 0.0224(12) -0.0076(13) C6 0.0422(13) 0.0535(14) 0.0330(12) -0.0055(11) 0.0171(11) -0.0025(11) C7 0.0458(13) 0.0431(13) 0.0386(12) -0.0094(11) 0.0226(11) -0.0083(11) C8 0.0596(16) 0.0496(15) 0.0414(13) -0.0061(12) 0.0208(12) -0.0106(13) C9 0.0737(18) 0.0349(13) 0.0510(15) -0.0038(11) 0.0298(14) -0.0107(13) C10 0.0667(17) 0.0399(14) 0.0405(13) -0.0001(11) 0.0222(12) 0.0012(12) C11 0.0520(14) 0.0349(12) 0.0404(13) -0.0028(10) 0.0189(11) -0.0030(11) C12 0.0454(13) 0.0368(12) 0.0355(12) -0.0015(10) 0.0192(11) -0.0003(11) C13 0.0411(13) 0.0377(12) 0.0332(12) 0.0079(10) 0.0133(10) 0.0007(10) C14 0.0477(13) 0.0411(13) 0.0538(14) 0.0036(11) 0.0334(12) -0.0021(11) C15 0.0491(13) 0.0379(12) 0.0474(13) 0.0064(11) 0.0320(11) -0.0014(11) C16 0.0366(12) 0.0342(12) 0.0327(11) 0.0114(10) 0.0078(10) 0.0065(9) C17 0.0315(13) 0.0376(13) 0.0776(18) -0.0030(12) 0.0053(12) 0.0075(11) C18 0.0371(13) 0.0380(13) 0.0671(17) -0.0039(12) 0.0085(12) 0.0076(11) C19 0.029(4) 0.040(4) 0.049(4) 0.009(3) 0.023(3) 0.004(3) C20 0.041(3) 0.036(3) 0.058(3) 0.006(3) 0.028(3) 0.005(2) C19' 0.039(4) 0.032(3) 0.047(4) 0.009(3) 0.021(3) 0.009(3) C20' 0.027(2) 0.043(3) 0.041(3) 0.004(3) 0.018(2) 0.004(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 C12 1.392(3) . ? N1 C1 1.400(3) . ? N1 C13 1.423(3) . ? C1 C2 1.388(3) . ? C1 C6 1.406(3) . ? C2 C3 1.387(3) . ? C2 H2A 0.9500 . ? C3 C4 1.381(3) . ? C3 H3A 0.9500 . ? C4 C5 1.374(3) . ? C4 H4A 0.9500 . ? C5 C6 1.401(3) . ? C5 H5A 0.9500 . ? C6 C7 1.436(3) . ? C7 C8 1.387(3) . ? C7 C12 1.410(3) . ? C8 C9 1.378(3) . ? C8 H8A 0.9500 . ? C9 C10 1.400(3) . ? C9 H9A 0.9500 . ? C10 C11 1.380(3) . ? C10 H10A 0.9500 . ? C11 C12 1.394(3) . ? C11 H11A 0.9500 . ? C13 C18 1.380(3) . ? C13 C14 1.382(3) . ? C14 C15 1.383(3) . ? C14 H14A 0.9500 . ? C15 C16 1.396(3) . ? C15 C19 1.478(7) . ? C15 C19' 1.579(6) . ? C16 C17 1.396(3) . ? C16 C16 1.471(4) 3_766 ? C17 C18 1.390(3) . ? C17 C20 1.448(5) . ? C17 C20' 1.655(5) . ? C18 H18A 0.9500 . ? C19 C20 1.523(8) 3_766 ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C19 1.523(8) 3_766 ? C20 H20C 0.9900 . ? C20 H20D 0.9900 . ? C19' C20' 1.522(8) 3_766 ? C19' H19C 0.9900 . ? C19' H19D 0.9900 . ? C20' C19' 1.522(8) 3_766 ? C20' H20A 0.9900 . ? C20' H20B 0.9900 . ? 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 C12 N1 C1 108.39(17) . . ? C12 N1 C13 126.43(17) . . ? C1 N1 C13 124.93(17) . . ? C2 C1 N1 129.1(2) . . ? C2 C1 C6 121.9(2) . . ? N1 C1 C6 108.94(19) . . ? C3 C2 C1 117.2(2) . . ? C3 C2 H2A 121.4 . . ? C1 C2 H2A 121.4 . . ? C4 C3 C2 122.1(2) . . ? C4 C3 H3A 119.0 . . ? C2 C3 H3A 119.0 . . ? C5 C4 C3 120.6(2) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 119.4(2) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? C5 C6 C1 118.8(2) . . ? C5 C6 C7 134.5(2) . . ? C1 C6 C7 106.67(18) . . ? C8 C7 C12 119.1(2) . . ? C8 C7 C6 133.4(2) . . ? C12 C7 C6 107.54(18) . . ? C9 C8 C7 119.0(2) . . ? C9 C8 H8A 120.5 . . ? C7 C8 H8A 120.5 . . ? C8 C9 C10 121.3(2) . . ? C8 C9 H9A 119.4 . . ? C10 C9 H9A 119.4 . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 117.3(2) . . ? C10 C11 H11A 121.3 . . ? C12 C11 H11A 121.3 . . ? N1 C12 C11 129.26(19) . . ? N1 C12 C7 108.45(18) . . ? C11 C12 C7 122.23(19) . . ? C18 C13 C14 119.8(2) . . ? C18 C13 N1 120.58(19) . . ? C14 C13 N1 119.63(18) . . ? C13 C14 C15 120.95(19) . . ? C13 C14 H14A 119.5 . . ? C15 C14 H14A 119.5 . . ? C14 C15 C16 119.44(19) . . ? C14 C15 C19 124.9(3) . . ? C16 C15 C19 114.2(3) . . ? C14 C15 C19' 117.6(3) . . ? C16 C15 C19' 121.0(3) . . ? C19 C15 C19' 26.9(2) . . ? C17 C16 C15 119.72(19) . . ? C17 C16 C16 120.2(2) . 3_766 ? C15 C16 C16 120.1(2) . 3_766 ? C18 C17 C16 119.8(2) . . ? C18 C17 C20 121.1(3) . . ? C16 C17 C20 116.8(3) . . ? C18 C17 C20' 120.7(3) . . ? C16 C17 C20' 116.5(2) . . ? C20 C17 C20' 32.4(2) . . ? C13 C18 C17 120.3(2) . . ? C13 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C15 C19 C20 111.9(4) . 3_766 ? C15 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 3_766 . ? C15 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 3_766 . ? H19A C19 H19B 107.9 . . ? C17 C20 C19 106.9(4) . 3_766 ? C17 C20 H20C 110.3 . . ? C19 C20 H20C 110.3 3_766 . ? C17 C20 H20D 110.3 . . ? C19 C20 H20D 110.3 3_766 . ? H20C C20 H20D 108.6 . . ? C20' C19' C15 105.4(4) 3_766 . ? C20' C19' H19C 110.7 3_766 . ? C15 C19' H19C 110.7 . . ? C20' C19' H19D 110.7 3_766 . ? C15 C19' H19D 110.7 . . ? H19C C19' H19D 108.8 . . ? C19' C20' C17 107.8(4) 3_766 . ? C19' C20' H20A 110.1 3_766 . ? C17 C20' H20A 110.1 . . ? C19' C20' H20B 110.1 3_766 . ? C17 C20' H20B 110.1 . . ? H20A C20' H20B 108.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.148 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.037 data_4b _database_code_depnum_ccdc_archive 'CCDC 899426' #TrackingRef '4b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H56 N2' _chemical_formula_sum 'C56 H56 N2' _chemical_formula_weight 757.03 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 17.743(2) _cell_length_b 10.9925(13) _cell_length_c 11.3555(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.023(2) _cell_angle_gamma 90.00 _cell_volume 2181.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4200 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 30.73 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method none _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5754 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 33652 _diffrn_reflns_av_R_equivalents 0.1055 _diffrn_reflns_av_sigmaI/netI 0.0903 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _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 2.19 _diffrn_reflns_theta_max 30.89 _reflns_number_total 6832 _reflns_number_gt 4004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0748P)^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 6832 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.29673(8) 0.78421(11) 0.32376(12) 0.0217(3) Uani 1 1 d . . . C1 C 0.29013(9) 0.90564(14) 0.35647(15) 0.0206(3) Uani 1 1 d . . . C2 C 0.33665(10) 0.97238(14) 0.44529(15) 0.0232(4) Uani 1 1 d . . . H2A H 0.3770 0.9351 0.4991 0.028 Uiso 1 1 calc R . . C3 C 0.32121(10) 1.09569(15) 0.45149(15) 0.0244(4) Uani 1 1 d . . . H3A H 0.3525 1.1430 0.5108 0.029 Uiso 1 1 calc R . . C4 C 0.26151(10) 1.15422(14) 0.37428(15) 0.0214(3) Uani 1 1 d . . . C5 C 0.21507(9) 1.08423(14) 0.28931(15) 0.0204(3) Uani 1 1 d . . . H5A H 0.1732 1.1209 0.2381 0.024 Uiso 1 1 calc R . . C6 C 0.22958(9) 0.95956(14) 0.27855(14) 0.0195(3) Uani 1 1 d . . . C7 C 0.19703(9) 0.86676(13) 0.19413(14) 0.0191(3) Uani 1 1 d . . . C8 C 0.13594(9) 0.86334(14) 0.09896(14) 0.0214(3) Uani 1 1 d . . . H8A H 0.1063 0.9346 0.0784 0.026 Uiso 1 1 calc R . . C9 C 0.11747(9) 0.75689(14) 0.03315(15) 0.0216(3) Uani 1 1 d . . . C10 C 0.16430(10) 0.65373(14) 0.06383(15) 0.0231(4) Uani 1 1 d . . . H10A H 0.1534 0.5815 0.0181 0.028 Uiso 1 1 calc R . . C11 C 0.22558(10) 0.65386(14) 0.15819(15) 0.0225(4) Uani 1 1 d . . . H11A H 0.2562 0.5833 0.1773 0.027 Uiso 1 1 calc R . . C12 C 0.24082(9) 0.76068(14) 0.22413(15) 0.0206(3) Uani 1 1 d . . . C13 C 0.35600(9) 0.70276(14) 0.37569(15) 0.0211(3) Uani 1 1 d . . . C14 C 0.35588(10) 0.65729(14) 0.48886(15) 0.0222(4) Uani 1 1 d . . . H14A H 0.3167 0.6805 0.5316 0.027 Uiso 1 1 calc R . . C15 C 0.41341(9) 0.57692(14) 0.54096(15) 0.0204(3) Uani 1 1 d . . . C16 C 0.47108(9) 0.54194(13) 0.47501(14) 0.0196(3) Uani 1 1 d . . . C17 C 0.47037(9) 0.58983(14) 0.35828(15) 0.0217(3) Uani 1 1 d . . . C18 C 0.41227(10) 0.67035(14) 0.31047(15) 0.0224(4) Uani 1 1 d . . . H18A H 0.4112 0.7032 0.2328 0.027 Uiso 1 1 calc R . . C19 C 0.41469(10) 0.52467(15) 0.65730(15) 0.0254(4) Uani 1 1 d . . . H19A H 0.3759 0.5463 0.7016 0.031 Uiso 1 1 calc R . . C20 C 0.53022(10) 0.55440(16) 0.29517(16) 0.0273(4) Uani 1 1 d . . . H20A H 0.5311 0.5874 0.2181 0.033 Uiso 1 1 calc R . . C21 C 0.25428(10) 1.29320(14) 0.38020(15) 0.0236(4) Uani 1 1 d . . . C22 C 0.18190(11) 1.34048(15) 0.29968(17) 0.0295(4) Uani 1 1 d . . . H22A H 0.1367 1.3054 0.3254 0.044 Uiso 1 1 calc R . . H22B H 0.1827 1.3170 0.2167 0.044 Uiso 1 1 calc R . . H22C H 0.1800 1.4293 0.3054 0.044 Uiso 1 1 calc R . . C23 C 0.25170(12) 1.33409(16) 0.50821(16) 0.0317(4) Uani 1 1 d . . . H23A H 0.2070 1.2982 0.5347 0.048 Uiso 1 1 calc R . . H23B H 0.2482 1.4230 0.5107 0.048 Uiso 1 1 calc R . . H23C H 0.2984 1.3073 0.5612 0.048 Uiso 1 1 calc R . . C24 C 0.32473(11) 1.34962(15) 0.33794(17) 0.0289(4) Uani 1 1 d . . . H24A H 0.3215 1.4385 0.3410 0.043 Uiso 1 1 calc R . . H24B H 0.3260 1.3238 0.2557 0.043 Uiso 1 1 calc R . . H24C H 0.3715 1.3223 0.3904 0.043 Uiso 1 1 calc R . . C25 C 0.04681(10) 0.75352(15) -0.06620(15) 0.0236(4) Uani 1 1 d . . . C26 C 0.05333(11) 0.85132(16) -0.16034(16) 0.0314(4) Uani 1 1 d . . . H26A H 0.0987 0.8354 -0.1964 0.047 Uiso 1 1 calc R . . H26B H 0.0580 0.9316 -0.1222 0.047 Uiso 1 1 calc R . . H26C H 0.0075 0.8494 -0.2225 0.047 Uiso 1 1 calc R . . C27 C -0.02445(10) 0.77922(17) -0.01027(17) 0.0316(4) Uani 1 1 d . . . H27A H -0.0701 0.7773 -0.0727 0.047 Uiso 1 1 calc R . . H27B H -0.0197 0.8596 0.0276 0.047 Uiso 1 1 calc R . . H27C H -0.0289 0.7171 0.0500 0.047 Uiso 1 1 calc R . . C28 C 0.03577(11) 0.62970(15) -0.12895(16) 0.0285(4) Uani 1 1 d . . . H28A H 0.0806 0.6113 -0.1655 0.043 Uiso 1 1 calc R . . H28B H -0.0101 0.6321 -0.1911 0.043 Uiso 1 1 calc R . . H28C H 0.0298 0.5666 -0.0704 0.043 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 0.0242(7) 0.0125(6) 0.0265(8) -0.0002(5) -0.0009(6) 0.0040(5) C1 0.0241(9) 0.0113(7) 0.0262(9) 0.0024(6) 0.0034(7) 0.0011(6) C2 0.0236(9) 0.0174(8) 0.0262(9) 0.0020(7) -0.0025(7) 0.0020(7) C3 0.0288(9) 0.0165(7) 0.0258(9) -0.0015(7) -0.0008(7) -0.0005(7) C4 0.0258(9) 0.0125(7) 0.0255(9) 0.0001(6) 0.0029(7) 0.0003(6) C5 0.0227(9) 0.0128(7) 0.0244(9) 0.0032(6) 0.0006(7) 0.0026(6) C6 0.0220(8) 0.0126(7) 0.0236(9) 0.0012(6) 0.0027(7) 0.0023(6) C7 0.0224(8) 0.0115(7) 0.0232(8) 0.0011(6) 0.0032(7) 0.0007(6) C8 0.0237(9) 0.0141(7) 0.0252(9) 0.0024(6) 0.0007(7) 0.0037(6) C9 0.0243(8) 0.0164(7) 0.0236(9) 0.0006(6) 0.0029(7) 0.0001(6) C10 0.0266(9) 0.0161(7) 0.0264(9) -0.0023(7) 0.0037(7) 0.0006(7) C11 0.0275(9) 0.0120(7) 0.0272(9) 0.0006(6) 0.0029(7) 0.0036(6) C12 0.0216(8) 0.0142(7) 0.0249(9) 0.0014(6) 0.0008(7) 0.0007(6) C13 0.0229(8) 0.0107(7) 0.0269(9) -0.0001(6) -0.0029(7) 0.0018(6) C14 0.0248(9) 0.0142(7) 0.0272(9) -0.0017(6) 0.0037(7) 0.0019(6) C15 0.0233(8) 0.0124(7) 0.0244(9) -0.0003(6) 0.0006(7) 0.0009(6) C16 0.0220(8) 0.0114(7) 0.0238(8) -0.0009(6) -0.0002(7) -0.0010(6) C17 0.0241(9) 0.0157(7) 0.0243(9) 0.0003(6) 0.0012(7) 0.0015(6) C18 0.0267(9) 0.0162(7) 0.0231(9) 0.0022(6) 0.0009(7) 0.0017(6) C19 0.0283(10) 0.0231(8) 0.0256(9) 0.0001(7) 0.0067(7) 0.0050(7) C20 0.0316(10) 0.0263(9) 0.0248(9) 0.0051(7) 0.0068(8) 0.0059(7) C21 0.0293(9) 0.0114(7) 0.0283(9) -0.0009(6) 0.0005(7) 0.0005(6) C22 0.0345(11) 0.0131(7) 0.0380(11) -0.0007(7) -0.0013(8) 0.0029(7) C23 0.0418(11) 0.0200(8) 0.0330(10) -0.0041(7) 0.0053(8) 0.0010(8) C24 0.0357(10) 0.0149(8) 0.0353(10) -0.0004(7) 0.0037(8) -0.0030(7) C25 0.0256(9) 0.0187(8) 0.0248(9) -0.0017(7) 0.0000(7) 0.0014(7) C26 0.0387(11) 0.0245(9) 0.0278(10) 0.0024(7) -0.0027(8) -0.0011(8) C27 0.0271(10) 0.0327(10) 0.0330(10) -0.0052(8) -0.0003(8) 0.0009(8) C28 0.0317(10) 0.0212(8) 0.0308(10) -0.0041(7) 0.0001(8) -0.0011(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 C12 1.393(2) . ? N1 C1 1.3959(19) . ? N1 C13 1.428(2) . ? C1 C2 1.395(2) . ? C1 C6 1.399(2) . ? C2 C3 1.387(2) . ? C2 H2A 0.9500 . ? C3 C4 1.408(2) . ? C3 H3A 0.9500 . ? C4 C5 1.388(2) . ? C4 C21 1.536(2) . ? C5 C6 1.404(2) . ? C5 H5A 0.9500 . ? C6 C7 1.449(2) . ? C7 C8 1.392(2) . ? C7 C12 1.410(2) . ? C8 C9 1.396(2) . ? C8 H8A 0.9500 . ? C9 C10 1.413(2) . ? C9 C25 1.534(2) . ? C10 C11 1.387(2) . ? C10 H10A 0.9500 . ? C11 C12 1.394(2) . ? C11 H11A 0.9500 . ? C13 C14 1.379(2) . ? C13 C18 1.389(2) . ? C14 C15 1.401(2) . ? C14 H14A 0.9500 . ? C15 C16 1.422(2) . ? C15 C19 1.437(2) . ? C16 C16 1.422(3) 3_666 ? C16 C17 1.424(2) . ? C17 C18 1.395(2) . ? C17 C20 1.435(2) . ? C18 H18A 0.9500 . ? C19 C20 1.349(2) 3_666 ? C19 H19A 0.9500 . ? C20 C19 1.349(2) 3_666 ? C20 H20A 0.9500 . ? C21 C23 1.530(2) . ? C21 C22 1.532(2) . ? C21 C24 1.545(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C28 1.533(2) . ? C25 C26 1.535(2) . ? C25 C27 1.537(2) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 C12 N1 C1 108.24(13) . . ? C12 N1 C13 126.03(13) . . ? C1 N1 C13 125.40(14) . . ? C2 C1 N1 128.96(15) . . ? C2 C1 C6 121.79(14) . . ? N1 C1 C6 109.11(14) . . ? C3 C2 C1 116.96(15) . . ? C3 C2 H2A 121.5 . . ? C1 C2 H2A 121.5 . . ? C2 C3 C4 123.29(16) . . ? C2 C3 H3A 118.4 . . ? C4 C3 H3A 118.4 . . ? C5 C4 C3 118.11(14) . . ? C5 C4 C21 122.55(15) . . ? C3 C4 C21 119.15(15) . . ? C4 C5 C6 120.40(15) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C1 C6 C5 119.40(15) . . ? C1 C6 C7 107.09(13) . . ? C5 C6 C7 133.37(15) . . ? C8 C7 C12 119.17(14) . . ? C8 C7 C6 134.39(14) . . ? C12 C7 C6 106.44(14) . . ? C7 C8 C9 121.12(14) . . ? C7 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? C8 C9 C10 117.86(15) . . ? C8 C9 C25 119.96(14) . . ? C10 C9 C25 122.15(14) . . ? C11 C10 C9 122.53(15) . . ? C11 C10 H10A 118.7 . . ? C9 C10 H10A 118.7 . . ? C10 C11 C12 117.94(14) . . ? C10 C11 H11A 121.0 . . ? C12 C11 H11A 121.0 . . ? N1 C12 C11 129.57(14) . . ? N1 C12 C7 109.10(13) . . ? C11 C12 C7 121.33(15) . . ? C14 C13 C18 121.44(15) . . ? C14 C13 N1 119.44(15) . . ? C18 C13 N1 119.12(15) . . ? C13 C14 C15 120.20(15) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C14 C15 C16 119.10(15) . . ? C14 C15 C19 122.29(15) . . ? C16 C15 C19 118.57(14) . . ? C16 C16 C15 120.04(19) 3_666 . ? C16 C16 C17 119.99(19) 3_666 . ? C15 C16 C17 119.96(14) . . ? C18 C17 C16 118.88(15) . . ? C18 C17 C20 122.61(15) . . ? C16 C17 C20 118.50(15) . . ? C13 C18 C17 120.41(15) . . ? C13 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C20 C19 C15 121.32(16) 3_666 . ? C20 C19 H19A 119.3 3_666 . ? C15 C19 H19A 119.3 . . ? C19 C20 C17 121.54(16) 3_666 . ? C19 C20 H20A 119.2 3_666 . ? C17 C20 H20A 119.2 . . ? C23 C21 C22 107.88(14) . . ? C23 C21 C4 110.52(14) . . ? C22 C21 C4 112.28(14) . . ? C23 C21 C24 109.69(14) . . ? C22 C21 C24 108.55(14) . . ? C4 C21 C24 107.90(14) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C28 C25 C9 112.66(14) . . ? C28 C25 C26 108.50(14) . . ? C9 C25 C26 110.15(14) . . ? C28 C25 C27 107.91(14) . . ? C9 C25 C27 108.51(14) . . ? C26 C25 C27 109.04(15) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N1 C1 C2 -175.25(17) . . . . ? C13 N1 C1 C2 -1.6(3) . . . . ? C12 N1 C1 C6 0.55(18) . . . . ? C13 N1 C1 C6 174.24(15) . . . . ? N1 C1 C2 C3 174.03(16) . . . . ? C6 C1 C2 C3 -1.3(2) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C2 C3 C4 C21 -173.86(16) . . . . ? C3 C4 C5 C6 -2.4(2) . . . . ? C21 C4 C5 C6 172.55(15) . . . . ? C2 C1 C6 C5 0.2(2) . . . . ? N1 C1 C6 C5 -175.96(14) . . . . ? C2 C1 C6 C7 176.46(15) . . . . ? N1 C1 C6 C7 0.31(18) . . . . ? C4 C5 C6 C1 1.7(2) . . . . ? C4 C5 C6 C7 -173.38(17) . . . . ? C1 C6 C7 C8 178.26(18) . . . . ? C5 C6 C7 C8 -6.2(3) . . . . ? C1 C6 C7 C12 -1.03(18) . . . . ? C5 C6 C7 C12 174.50(17) . . . . ? C12 C7 C8 C9 0.0(2) . . . . ? C6 C7 C8 C9 -179.18(17) . . . . ? C7 C8 C9 C10 -2.0(2) . . . . ? C7 C8 C9 C25 176.17(15) . . . . ? C8 C9 C10 C11 2.1(2) . . . . ? C25 C9 C10 C11 -176.04(16) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C1 N1 C12 C11 178.76(17) . . . . ? C13 N1 C12 C11 5.1(3) . . . . ? C1 N1 C12 C7 -1.22(18) . . . . ? C13 N1 C12 C7 -174.86(15) . . . . ? C10 C11 C12 N1 178.11(16) . . . . ? C10 C11 C12 C7 -1.9(2) . . . . ? C8 C7 C12 N1 -178.04(14) . . . . ? C6 C7 C12 N1 1.38(18) . . . . ? C8 C7 C12 C11 2.0(2) . . . . ? C6 C7 C12 C11 -178.60(15) . . . . ? C12 N1 C13 C14 -113.78(18) . . . . ? C1 N1 C13 C14 73.6(2) . . . . ? C12 N1 C13 C18 65.7(2) . . . . ? C1 N1 C13 C18 -106.87(19) . . . . ? C18 C13 C14 C15 0.3(2) . . . . ? N1 C13 C14 C15 179.74(14) . . . . ? C13 C14 C15 C16 -0.8(2) . . . . ? C13 C14 C15 C19 -178.37(15) . . . . ? C14 C15 C16 C16 -178.42(18) . . . 3_666 ? C19 C15 C16 C16 -0.7(3) . . . 3_666 ? C14 C15 C16 C17 0.8(2) . . . . ? C19 C15 C16 C17 178.50(15) . . . . ? C16 C16 C17 C18 178.91(18) 3_666 . . . ? C15 C16 C17 C18 -0.3(2) . . . . ? C16 C16 C17 C20 -1.9(3) 3_666 . . . ? C15 C16 C17 C20 178.84(15) . . . . ? C14 C13 C18 C17 0.3(2) . . . . ? N1 C13 C18 C17 -179.23(15) . . . . ? C16 C17 C18 C13 -0.2(2) . . . . ? C20 C17 C18 C13 -179.35(16) . . . . ? C14 C15 C19 C20 178.68(17) . . . 3_666 ? C16 C15 C19 C20 1.1(3) . . . 3_666 ? C18 C17 C20 C19 -179.25(17) . . . 3_666 ? C16 C17 C20 C19 1.6(3) . . . 3_666 ? C5 C4 C21 C23 131.47(17) . . . . ? C3 C4 C21 C23 -53.7(2) . . . . ? C5 C4 C21 C22 11.0(2) . . . . ? C3 C4 C21 C22 -174.17(15) . . . . ? C5 C4 C21 C24 -108.61(18) . . . . ? C3 C4 C21 C24 66.3(2) . . . . ? C8 C9 C25 C28 179.75(15) . . . . ? C10 C9 C25 C28 -2.2(2) . . . . ? C8 C9 C25 C26 58.5(2) . . . . ? C10 C9 C25 C26 -123.46(17) . . . . ? C8 C9 C25 C27 -60.8(2) . . . . ? C10 C9 C25 C27 117.24(17) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.89 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.336 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.057