# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H20 N2' _chemical_formula_weight 372.45 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.164(3) _cell_length_b 6.6995(13) _cell_length_c 19.809(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.08(3) _cell_angle_gamma 90.00 _cell_volume 2125.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11249 _cell_measurement_theta_min 6.17 _cell_measurement_theta_max 55.16 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19408 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4844 _reflns_number_gt 2434 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _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^)+(0.0682P)^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 4844 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C22 C 0.12451(10) 0.2971(2) 1.11003(9) 0.0483(4) Uani 1 1 d . . . C19 C 0.10419(10) 0.2015(2) 0.98319(9) 0.0503(4) Uani 1 1 d . . . H2A H 0.1065 0.0703 0.9992 0.060 Uiso 1 1 calc R . . C18 C 0.03779(11) 0.3953(3) 0.79244(9) 0.0547(5) Uani 1 1 d . . . H3A H 0.0099 0.5045 0.7655 0.066 Uiso 1 1 calc R . . C17 C 0.05007(10) 0.3850(2) 0.86457(9) 0.0527(5) Uani 1 1 d . . . H4A H 0.0310 0.4886 0.8858 0.063 Uiso 1 1 calc R . . C20 C 0.11418(9) 0.3404(2) 1.03439(9) 0.0458(4) Uani 1 1 d . . . C15 C 0.11740(12) 0.0719(3) 0.87231(10) 0.0590(5) Uani 1 1 d . . . H6A H 0.1434 -0.0398 0.8987 0.071 Uiso 1 1 calc R . . N1 N 0.05246(10) 0.2565(2) 0.68487(8) 0.0669(5) Uani 1 1 d . . . C16 C 0.09034(10) 0.2232(2) 0.90687(9) 0.0490(4) Uani 1 1 d . . . C13 C 0.06621(11) 0.2455(3) 0.75891(10) 0.0545(5) Uani 1 1 d . . . C14 C 0.10665(12) 0.0835(3) 0.80033(10) 0.0635(5) Uani 1 1 d . . . H10A H 0.1267 -0.0184 0.7791 0.076 Uiso 1 1 calc R . . C7 C -0.02074(11) 0.3497(3) 0.63669(9) 0.0551(5) Uani 1 1 d . . . C27 C 0.16443(12) 0.4286(3) 1.16521(11) 0.0664(5) Uani 1 1 d . . . H12A H 0.1856 0.5474 1.1545 0.080 Uiso 1 1 calc R . . C21 C 0.12121(13) 0.5460(3) 1.01817(10) 0.0658(6) Uani 1 1 d . . . C23 C 0.09356(13) 0.1232(3) 1.12843(11) 0.0690(6) Uani 1 1 d . . . H14A H 0.0662 0.0313 1.0925 0.083 Uiso 1 1 calc R . . C6 C 0.07646(14) 0.0262(3) 0.60048(12) 0.0736(6) Uani 1 1 d . . . H15A H 0.0196 -0.0015 0.5818 0.088 Uiso 1 1 calc R . . C24 C 0.10255(15) 0.0838(4) 1.19893(12) 0.0859(7) Uani 1 1 d . . . H16A H 0.0815 -0.0343 1.2102 0.103 Uiso 1 1 calc R . . C1 C 0.10715(11) 0.1589(3) 0.65603(10) 0.0576(5) Uani 1 1 d . . . C25 C 0.14217(14) 0.2167(4) 1.25255(12) 0.0826(7) Uani 1 1 d . . . H18A H 0.1476 0.1905 1.3001 0.099 Uiso 1 1 calc R . . C26 C 0.17365(14) 0.3883(4) 1.23559(12) 0.0802(7) Uani 1 1 d . . . H19A H 0.2015 0.4785 1.2719 0.096 Uiso 1 1 calc R . . C4 C 0.21259(18) -0.0270(4) 0.59893(15) 0.0902(8) Uani 1 1 d . . . H20A H 0.2482 -0.0900 0.5796 0.108 Uiso 1 1 calc R . . C3 C 0.24373(15) 0.1059(4) 0.65434(16) 0.0927(8) Uani 1 1 d . . . H21A H 0.3006 0.1334 0.6727 0.111 Uiso 1 1 calc R . . C12 C -0.01473(14) 0.4939(3) 0.59017(12) 0.0788(6) Uani 1 1 d . . . H22A H 0.0374 0.5302 0.5898 0.095 Uiso 1 1 calc R . . C8 C -0.09845(13) 0.3000(4) 0.63578(11) 0.0796(7) Uani 1 1 d . . . H23A H -0.1042 0.2012 0.6666 0.096 Uiso 1 1 calc R . . C5 C 0.12921(18) -0.0670(3) 0.57197(13) 0.0890(7) Uani 1 1 d . . . H24A H 0.1078 -0.1575 0.5342 0.107 Uiso 1 1 calc R . . C2 C 0.19130(13) 0.1996(3) 0.68326(13) 0.0807(7) Uani 1 1 d . . . H25A H 0.2128 0.2900 0.7211 0.097 Uiso 1 1 calc R . . N2 N 0.12939(17) 0.7101(3) 1.00870(11) 0.1153(9) Uani 1 1 d . . . C10 C -0.16181(17) 0.5369(4) 0.54364(13) 0.0963(8) Uani 1 1 d . . . H27A H -0.2093 0.6002 0.5123 0.116 Uiso 1 1 calc R . . C9 C -0.16842(14) 0.3960(5) 0.58926(13) 0.1001(9) Uani 1 1 d . . . H28A H -0.2208 0.3624 0.5896 0.120 Uiso 1 1 calc R . . C11 C -0.08553(18) 0.5859(4) 0.54368(14) 0.0981(8) Uani 1 1 d . . . H29A H -0.0807 0.6832 0.5119 0.118 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 C22 0.0465(9) 0.0511(9) 0.0488(10) 0.0011(8) 0.0189(8) 0.0025(8) C19 0.0579(10) 0.0418(9) 0.0507(10) 0.0048(8) 0.0190(8) -0.0002(8) C18 0.0547(10) 0.0575(10) 0.0512(11) 0.0128(8) 0.0181(8) 0.0134(8) C17 0.0512(10) 0.0551(10) 0.0520(11) 0.0041(8) 0.0189(8) 0.0092(8) C20 0.0478(9) 0.0411(8) 0.0504(10) 0.0048(8) 0.0201(8) 0.0004(7) C15 0.0742(12) 0.0485(10) 0.0530(11) 0.0058(8) 0.0212(9) 0.0108(9) N1 0.0645(10) 0.0920(12) 0.0483(9) 0.0127(8) 0.0251(8) 0.0253(9) C16 0.0517(10) 0.0472(9) 0.0482(10) 0.0046(8) 0.0182(8) 0.0005(8) C13 0.0540(10) 0.0643(11) 0.0473(10) 0.0064(9) 0.0207(8) 0.0096(9) C14 0.0799(13) 0.0587(11) 0.0534(12) 0.0023(9) 0.0257(10) 0.0184(10) C7 0.0551(10) 0.0677(11) 0.0449(10) 0.0062(9) 0.0211(8) 0.0058(9) C27 0.0754(13) 0.0677(12) 0.0585(12) -0.0063(10) 0.0271(10) -0.0056(10) C21 0.0920(15) 0.0473(11) 0.0567(12) -0.0020(9) 0.0250(11) -0.0048(10) C23 0.0774(13) 0.0741(13) 0.0552(12) 0.0053(10) 0.0235(10) -0.0183(11) C6 0.0770(14) 0.0753(13) 0.0706(14) -0.0052(11) 0.0290(12) 0.0062(11) C24 0.0930(16) 0.1025(17) 0.0652(14) 0.0187(13) 0.0319(12) -0.0200(14) C1 0.0639(11) 0.0632(11) 0.0513(11) 0.0077(9) 0.0275(9) 0.0110(10) C25 0.0763(14) 0.122(2) 0.0513(13) 0.0121(13) 0.0258(11) 0.0065(14) C26 0.0837(15) 0.0975(17) 0.0580(13) -0.0156(12) 0.0240(11) -0.0038(13) C4 0.106(2) 0.0853(16) 0.106(2) 0.0115(15) 0.0691(17) 0.0308(15) C3 0.0719(14) 0.0939(17) 0.126(2) -0.0035(16) 0.0526(15) 0.0082(13) C12 0.0725(13) 0.0847(15) 0.0838(15) 0.0266(12) 0.0337(12) 0.0049(12) C8 0.0636(13) 0.1147(18) 0.0597(13) 0.0115(12) 0.0211(10) -0.0135(12) C5 0.111(2) 0.0794(15) 0.0830(16) -0.0074(13) 0.0420(15) 0.0184(15) C2 0.0661(13) 0.0837(15) 0.0966(17) -0.0168(13) 0.0346(12) -0.0007(11) N2 0.204(2) 0.0452(10) 0.0900(15) 0.0024(9) 0.0454(16) -0.0178(12) C10 0.0832(18) 0.134(2) 0.0618(15) 0.0035(15) 0.0139(13) 0.0351(16) C9 0.0529(12) 0.174(3) 0.0683(15) -0.0002(18) 0.0151(11) -0.0027(15) C11 0.110(2) 0.0925(17) 0.0903(18) 0.0364(14) 0.0341(16) 0.0262(16) _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 C22 C27 1.379(2) . ? C22 C23 1.383(2) . ? C22 C20 1.473(2) . ? C19 C20 1.341(2) . ? C19 C16 1.451(2) . ? C19 H2A 0.9300 . ? C18 C17 1.369(2) . ? C18 C13 1.385(2) . ? C18 H3A 0.9300 . ? C17 C16 1.392(2) . ? C17 H4A 0.9300 . ? C20 C21 1.430(2) . ? C15 C14 1.372(3) . ? C15 C16 1.393(2) . ? C15 H6A 0.9300 . ? N1 C13 1.401(2) . ? N1 C7 1.420(2) . ? N1 C1 1.421(2) . ? C13 C14 1.387(2) . ? C14 H10A 0.9300 . ? C7 C12 1.364(3) . ? C7 C8 1.368(3) . ? C27 C26 1.372(3) . ? C27 H12A 0.9300 . ? C21 N2 1.132(2) . ? C23 C24 1.374(3) . ? C23 H14A 0.9300 . ? C6 C1 1.365(3) . ? C6 C5 1.377(3) . ? C6 H15A 0.9300 . ? C24 C25 1.365(3) . ? C24 H16A 0.9300 . ? C1 C2 1.375(3) . ? C25 C26 1.362(3) . ? C25 H18A 0.9300 . ? C26 H19A 0.9300 . ? C4 C5 1.362(3) . ? C4 C3 1.364(3) . ? C4 H20A 0.9300 . ? C3 C2 1.379(3) . ? C3 H21A 0.9300 . ? C12 C11 1.379(3) . ? C12 H22A 0.9300 . ? C8 C9 1.382(3) . ? C8 H23A 0.9300 . ? C5 H24A 0.9300 . ? C2 H25A 0.9300 . ? C10 C9 1.339(3) . ? C10 C11 1.350(4) . ? C10 H27A 0.9300 . ? C9 H28A 0.9300 . ? C11 H29A 0.9300 . ? 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 C27 C22 C23 117.26(18) . . ? C27 C22 C20 121.62(16) . . ? C23 C22 C20 121.11(16) . . ? C20 C19 C16 130.30(16) . . ? C20 C19 H2A 114.9 . . ? C16 C19 H2A 114.9 . . ? C17 C18 C13 121.03(16) . . ? C17 C18 H3A 119.5 . . ? C13 C18 H3A 119.5 . . ? C18 C17 C16 121.60(17) . . ? C18 C17 H4A 119.2 . . ? C16 C17 H4A 119.2 . . ? C19 C20 C21 119.80(16) . . ? C19 C20 C22 124.65(15) . . ? C21 C20 C22 115.42(15) . . ? C14 C15 C16 121.69(17) . . ? C14 C15 H6A 119.2 . . ? C16 C15 H6A 119.2 . . ? C13 N1 C7 120.11(16) . . ? C13 N1 C1 120.65(15) . . ? C7 N1 C1 118.98(15) . . ? C17 C16 C15 116.87(16) . . ? C17 C16 C19 124.41(17) . . ? C15 C16 C19 118.71(15) . . ? C18 C13 C14 118.09(17) . . ? C18 C13 N1 120.55(16) . . ? C14 C13 N1 121.34(17) . . ? C15 C14 C13 120.69(18) . . ? C15 C14 H10A 119.7 . . ? C13 C14 H10A 119.7 . . ? C12 C7 C8 118.25(18) . . ? C12 C7 N1 120.10(18) . . ? C8 C7 N1 121.64(18) . . ? C26 C27 C22 121.5(2) . . ? C26 C27 H12A 119.3 . . ? C22 C27 H12A 119.3 . . ? N2 C21 C20 176.6(2) . . ? C24 C23 C22 121.1(2) . . ? C24 C23 H14A 119.5 . . ? C22 C23 H14A 119.5 . . ? C1 C6 C5 120.4(2) . . ? C1 C6 H15A 119.8 . . ? C5 C6 H15A 119.8 . . ? C25 C24 C23 120.5(2) . . ? C25 C24 H16A 119.7 . . ? C23 C24 H16A 119.7 . . ? C6 C1 C2 119.5(2) . . ? C6 C1 N1 120.30(18) . . ? C2 C1 N1 120.24(18) . . ? C26 C25 C24 119.3(2) . . ? C26 C25 H18A 120.4 . . ? C24 C25 H18A 120.4 . . ? C25 C26 C27 120.4(2) . . ? C25 C26 H19A 119.8 . . ? C27 C26 H19A 119.8 . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H20A 120.1 . . ? C3 C4 H20A 120.1 . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H21A 119.8 . . ? C2 C3 H21A 119.8 . . ? C7 C12 C11 120.3(2) . . ? C7 C12 H22A 119.8 . . ? C11 C12 H22A 119.8 . . ? C7 C8 C9 120.3(2) . . ? C7 C8 H23A 119.8 . . ? C9 C8 H23A 119.8 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H24A 119.9 . . ? C6 C5 H24A 119.9 . . ? C1 C2 C3 119.8(2) . . ? C1 C2 H25A 120.1 . . ? C3 C2 H25A 120.1 . . ? C9 C10 C11 119.3(2) . . ? C9 C10 H27A 120.4 . . ? C11 C10 H27A 120.4 . . ? C10 C9 C8 120.9(2) . . ? C10 C9 H28A 119.5 . . ? C8 C9 H28A 119.5 . . ? C10 C11 C12 120.9(2) . . ? C10 C11 H29A 119.6 . . ? C12 C11 H29A 119.6 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.132 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.033 _database_code_depnum_ccdc_archive 'CCDC 968916' ####################################################################### # # 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_13 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H19 N3 O2' _chemical_formula_weight 417.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.154(2) _cell_length_b 7.5463(15) _cell_length_c 25.707(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.42(3) _cell_angle_gamma 90.00 _cell_volume 2150.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11289 _cell_measurement_theta_min 6.27 _cell_measurement_theta_max 55.05 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.990 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19989 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4896 _reflns_number_gt 2488 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _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^)+(0.0628P)^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 4896 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1153 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _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 0.28772(13) -0.31451(18) 0.17385(6) 0.0570(4) Uani 1 1 d . . . C1 C 0.18492(16) -0.4059(2) 0.18840(7) 0.0494(4) Uani 1 1 d . . . C15 C 0.17213(18) 0.1159(2) 0.12112(7) 0.0569(5) Uani 1 1 d . . . H3A H 0.1139 0.1985 0.1278 0.068 Uiso 1 1 calc R . . C16 C 0.24141(17) 0.1465(2) 0.07990(7) 0.0543(5) Uani 1 1 d . . . C19 C 0.22061(18) 0.3103(2) 0.05056(7) 0.0593(5) Uani 1 1 d . . . H5A H 0.1601 0.3807 0.0618 0.071 Uiso 1 1 calc R . . C20 C 0.27189(18) 0.3794(2) 0.01048(7) 0.0589(5) Uani 1 1 d . . . C14 C 0.18742(17) -0.0323(2) 0.15202(7) 0.0571(5) Uani 1 1 d . . . H7A H 0.1402 -0.0476 0.1793 0.069 Uiso 1 1 calc R . . C13 C 0.27260(16) -0.1598(2) 0.14308(7) 0.0526(4) Uani 1 1 d . . . C18 C 0.34198(18) -0.1311(2) 0.10234(7) 0.0615(5) Uani 1 1 d . . . H9A H 0.3996 -0.2147 0.0957 0.074 Uiso 1 1 calc R . . C2 C 0.07690(16) -0.4076(2) 0.15596(7) 0.0541(5) Uani 1 1 d . . . H10A H 0.0699 -0.3446 0.1247 0.065 Uiso 1 1 calc R . . C17 C 0.32766(18) 0.0175(2) 0.07156(8) 0.0627(5) Uani 1 1 d . . . H11A H 0.3760 0.0330 0.0447 0.075 Uiso 1 1 calc R . . C7 C 0.40222(16) -0.4005(2) 0.18057(7) 0.0509(4) Uani 1 1 d . . . C22 C 0.2373(2) 0.5518(2) -0.01488(7) 0.0619(5) Uani 1 1 d . . . C4 C -0.0109(2) -0.5978(3) 0.21567(9) 0.0728(6) Uani 1 1 d . . . H14A H -0.0759 -0.6643 0.2244 0.087 Uiso 1 1 calc R . . C5 C 0.0954(2) -0.5940(3) 0.24817(9) 0.0700(6) Uani 1 1 d . . . H15A H 0.1019 -0.6573 0.2794 0.084 Uiso 1 1 calc R . . C12 C 0.41198(18) -0.5795(2) 0.17168(8) 0.0630(5) Uani 1 1 d . . . H16A H 0.3431 -0.6454 0.1611 0.076 Uiso 1 1 calc R . . C8 C 0.50596(19) -0.3064(3) 0.19627(9) 0.0730(6) Uani 1 1 d . . . H17A H 0.5016 -0.1856 0.2030 0.088 Uiso 1 1 calc R . . C3 C -0.01981(18) -0.5018(3) 0.16988(9) 0.0661(5) Uani 1 1 d . . . H18A H -0.0922 -0.5008 0.1481 0.079 Uiso 1 1 calc R . . C6 C 0.19263(18) -0.4980(2) 0.23517(8) 0.0592(5) Uani 1 1 d . . . H19A H 0.2636 -0.4950 0.2579 0.071 Uiso 1 1 calc R . . C25 C 0.1786(3) 0.8747(3) -0.06142(9) 0.0825(7) Uani 1 1 d . . . C11 C 0.5230(2) -0.6620(3) 0.17829(9) 0.0776(6) Uani 1 1 d . . . H21A H 0.5283 -0.7831 0.1723 0.093 Uiso 1 1 calc R . . C23 C 0.1390(2) 0.6479(3) -0.00242(9) 0.0764(6) Uani 1 1 d . . . H22A H 0.0915 0.6024 0.0219 0.092 Uiso 1 1 calc R . . C10 C 0.6246(2) -0.5674(3) 0.19357(10) 0.0853(7) Uani 1 1 d . . . H23A H 0.6993 -0.6233 0.1982 0.102 Uiso 1 1 calc R . . C9 C 0.6160(2) -0.3910(3) 0.20194(11) 0.0906(7) Uani 1 1 d . . . H24A H 0.6857 -0.3259 0.2117 0.109 Uiso 1 1 calc R . . C24 C 0.1097(2) 0.8097(3) -0.02530(9) 0.0845(7) Uani 1 1 d . . . H25A H 0.0438 0.8736 -0.0162 0.101 Uiso 1 1 calc R . . N3 N 0.1487(3) 1.0481(3) -0.08568(11) 0.1086(9) Uani 1 1 d . . . C21 C 0.3658(3) 0.2877(3) -0.01159(10) 0.0850(7) Uani 1 1 d . . . C26 C 0.2743(3) 0.7847(4) -0.07526(10) 0.1028(9) Uani 1 1 d . . . H28A H 0.3201 0.8308 -0.1001 0.123 Uiso 1 1 calc R . . O1 O 0.0762(2) 1.1416(3) -0.06569(9) 0.1242(8) Uani 1 1 d . . . C27 C 0.3036(3) 0.6228(3) -0.05204(9) 0.0926(8) Uani 1 1 d . . . H30A H 0.3695 0.5603 -0.0617 0.111 Uiso 1 1 calc R . . O2 O 0.1978(3) 1.0924(3) -0.12339(10) 0.1671(11) Uani 1 1 d . . . N2 N 0.4403(3) 0.2189(3) -0.03063(11) 0.1397(11) 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 0.0453(9) 0.0535(8) 0.0738(10) 0.0136(8) 0.0132(8) 0.0013(7) C1 0.0461(11) 0.0439(9) 0.0601(10) 0.0028(8) 0.0148(8) 0.0018(8) C15 0.0621(12) 0.0454(10) 0.0658(12) -0.0001(9) 0.0180(10) 0.0012(8) C16 0.0639(12) 0.0449(9) 0.0547(10) -0.0006(8) 0.0098(9) -0.0009(9) C19 0.0705(14) 0.0493(10) 0.0589(11) 0.0012(9) 0.0109(10) 0.0024(9) C20 0.0665(13) 0.0550(11) 0.0546(11) 0.0013(9) 0.0046(9) -0.0032(9) C14 0.0629(13) 0.0470(10) 0.0652(11) 0.0041(9) 0.0235(9) -0.0020(9) C13 0.0527(11) 0.0451(9) 0.0611(11) 0.0051(9) 0.0119(9) -0.0014(8) C18 0.0660(13) 0.0538(11) 0.0679(12) 0.0080(9) 0.0211(10) 0.0107(9) C2 0.0523(12) 0.0505(10) 0.0599(11) 0.0042(9) 0.0088(9) 0.0039(8) C17 0.0695(14) 0.0595(11) 0.0628(11) 0.0075(10) 0.0243(10) 0.0059(10) C7 0.0422(10) 0.0538(10) 0.0571(10) 0.0036(8) 0.0072(8) -0.0024(8) C22 0.0758(15) 0.0577(11) 0.0508(10) 0.0043(9) 0.0009(10) -0.0070(10) C4 0.0566(14) 0.0614(12) 0.1058(17) 0.0130(12) 0.0332(13) -0.0004(10) C5 0.0709(15) 0.0661(12) 0.0778(14) 0.0207(11) 0.0300(12) 0.0071(11) C12 0.0501(12) 0.0596(11) 0.0788(13) -0.0063(10) 0.0048(10) -0.0034(9) C8 0.0579(14) 0.0635(12) 0.0962(16) -0.0053(12) 0.0032(12) -0.0111(10) C3 0.0458(12) 0.0583(11) 0.0953(15) -0.0003(11) 0.0129(10) 0.0031(9) C6 0.0553(12) 0.0595(11) 0.0642(11) 0.0092(10) 0.0120(9) 0.0060(9) C25 0.113(2) 0.0620(13) 0.0660(14) 0.0177(12) -0.0198(14) -0.0128(13) C11 0.0594(14) 0.0674(13) 0.1072(18) -0.0025(12) 0.0147(12) 0.0093(11) C23 0.0899(17) 0.0588(12) 0.0806(15) 0.0145(11) 0.0105(13) 0.0016(12) C10 0.0472(13) 0.0917(17) 0.1162(19) 0.0102(15) 0.0055(13) 0.0092(12) C9 0.0479(14) 0.0942(17) 0.127(2) -0.0052(15) -0.0032(13) -0.0166(12) C24 0.0972(19) 0.0603(13) 0.0925(17) 0.0116(13) -0.0046(14) 0.0053(12) N3 0.148(3) 0.0759(16) 0.0909(17) 0.0262(14) -0.0328(17) -0.0115(15) C21 0.097(2) 0.0802(15) 0.0839(16) 0.0271(13) 0.0355(14) 0.0135(14) C26 0.132(3) 0.0969(19) 0.0814(17) 0.0346(15) 0.0223(17) -0.0037(18) O1 0.162(2) 0.0717(12) 0.1264(18) 0.0242(12) -0.0377(15) 0.0027(12) C27 0.117(2) 0.0819(16) 0.0837(16) 0.0281(13) 0.0296(15) 0.0087(14) O2 0.240(3) 0.1346(19) 0.1239(18) 0.0792(15) 0.009(2) 0.0000(17) N2 0.155(3) 0.136(2) 0.146(2) 0.0610(18) 0.096(2) 0.0598(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C13 1.410(2) . ? N1 C1 1.423(2) . ? N1 C7 1.426(2) . ? C1 C6 1.383(2) . ? C1 C2 1.387(2) . ? C15 C14 1.371(2) . ? C15 C16 1.399(3) . ? C15 H3A 0.9300 . ? C16 C17 1.402(2) . ? C16 C19 1.453(2) . ? C19 C20 1.339(3) . ? C19 H5A 0.9300 . ? C20 C21 1.426(3) . ? C20 C22 1.487(3) . ? C14 C13 1.389(2) . ? C14 H7A 0.9300 . ? C13 C18 1.387(3) . ? C18 C17 1.372(3) . ? C18 H9A 0.9300 . ? C2 C3 1.372(3) . ? C2 H10A 0.9300 . ? C17 H11A 0.9300 . ? C7 C12 1.376(2) . ? C7 C8 1.379(3) . ? C22 C27 1.380(3) . ? C22 C23 1.382(3) . ? C4 C5 1.373(3) . ? C4 C3 1.376(3) . ? C4 H14A 0.9300 . ? C5 C6 1.376(3) . ? C5 H15A 0.9300 . ? C12 C11 1.379(3) . ? C12 H16A 0.9300 . ? C8 C9 1.377(3) . ? C8 H17A 0.9300 . ? C3 H18A 0.9300 . ? C6 H19A 0.9300 . ? C25 C26 1.346(4) . ? C25 C24 1.362(3) . ? C25 N3 1.471(3) . ? C11 C10 1.360(3) . ? C11 H21A 0.9300 . ? C23 C24 1.379(3) . ? C23 H22A 0.9300 . ? C10 C9 1.353(3) . ? C10 H23A 0.9300 . ? C9 H24A 0.9300 . ? C24 H25A 0.9300 . ? N3 O2 1.213(3) . ? N3 O1 1.229(3) . ? C21 N2 1.136(3) . ? C26 C27 1.383(3) . ? C26 H28A 0.9300 . ? C27 H30A 0.9300 . ? 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 C13 N1 C1 119.96(14) . . ? C13 N1 C7 119.63(15) . . ? C1 N1 C7 118.98(14) . . ? C6 C1 C2 118.92(17) . . ? C6 C1 N1 119.89(16) . . ? C2 C1 N1 121.18(16) . . ? C14 C15 C16 122.03(17) . . ? C14 C15 H3A 119.0 . . ? C16 C15 H3A 119.0 . . ? C15 C16 C17 116.60(17) . . ? C15 C16 C19 117.66(17) . . ? C17 C16 C19 125.72(18) . . ? C20 C19 C16 132.34(19) . . ? C20 C19 H5A 113.8 . . ? C16 C19 H5A 113.8 . . ? C19 C20 C21 120.90(18) . . ? C19 C20 C22 124.48(19) . . ? C21 C20 C22 114.62(18) . . ? C15 C14 C13 120.78(18) . . ? C15 C14 H7A 119.6 . . ? C13 C14 H7A 119.6 . . ? C18 C13 C14 117.82(16) . . ? C18 C13 N1 120.72(16) . . ? C14 C13 N1 121.46(17) . . ? C17 C18 C13 121.63(18) . . ? C17 C18 H9A 119.2 . . ? C13 C18 H9A 119.2 . . ? C3 C2 C1 120.22(18) . . ? C3 C2 H10A 119.9 . . ? C1 C2 H10A 119.9 . . ? C18 C17 C16 121.14(19) . . ? C18 C17 H11A 119.4 . . ? C16 C17 H11A 119.4 . . ? C12 C7 C8 118.34(18) . . ? C12 C7 N1 120.87(16) . . ? C8 C7 N1 120.78(17) . . ? C27 C22 C23 117.2(2) . . ? C27 C22 C20 120.7(2) . . ? C23 C22 C20 122.09(19) . . ? C5 C4 C3 118.97(19) . . ? C5 C4 H14A 120.5 . . ? C3 C4 H14A 120.5 . . ? C4 C5 C6 120.92(19) . . ? C4 C5 H15A 119.5 . . ? C6 C5 H15A 119.5 . . ? C7 C12 C11 120.63(19) . . ? C7 C12 H16A 119.7 . . ? C11 C12 H16A 119.7 . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H17A 120.0 . . ? C7 C8 H17A 120.0 . . ? C2 C3 C4 120.8(2) . . ? C2 C3 H18A 119.6 . . ? C4 C3 H18A 119.6 . . ? C5 C6 C1 120.11(19) . . ? C5 C6 H19A 119.9 . . ? C1 C6 H19A 119.9 . . ? C26 C25 C24 121.6(2) . . ? C26 C25 N3 119.1(3) . . ? C24 C25 N3 119.4(3) . . ? C10 C11 C12 120.4(2) . . ? C10 C11 H21A 119.8 . . ? C12 C11 H21A 119.8 . . ? C24 C23 C22 121.5(2) . . ? C24 C23 H22A 119.3 . . ? C22 C23 H22A 119.3 . . ? C9 C10 C11 119.4(2) . . ? C9 C10 H23A 120.3 . . ? C11 C10 H23A 120.3 . . ? C10 C9 C8 121.1(2) . . ? C10 C9 H24A 119.4 . . ? C8 C9 H24A 119.4 . . ? C25 C24 C23 119.0(2) . . ? C25 C24 H25A 120.5 . . ? C23 C24 H25A 120.5 . . ? O2 N3 O1 123.6(3) . . ? O2 N3 C25 118.9(3) . . ? O1 N3 C25 117.5(3) . . ? N2 C21 C20 177.5(3) . . ? C25 C26 C27 119.2(3) . . ? C25 C26 H28A 120.4 . . ? C27 C26 H28A 120.4 . . ? C22 C27 C26 121.5(3) . . ? C22 C27 H30A 119.2 . . ? C26 C27 H30A 119.2 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.158 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 968917'