# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Toshiaki Murai' _publ_contact_author_email mtoshi@gifu-u.ac.jp loop_ _publ_author_name 'Toshiaki Murai' 'Eri Nagaya' 'Fumitoshi Shibahara' 'Toshifumi Maruyama' data_en013-3 _database_code_depnum_ccdc_archive 'CCDC 868371' #TrackingRef '9731_web_deposit_cif_file_0_ToshiakiMurai_1329874131.en013-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H32 N4' _chemical_formula_sum 'C41 H32 N4' _chemical_formula_weight 580.71 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 'C 2/c ' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.232(18) _cell_length_b 10.636(7) _cell_length_c 17.824(14) _cell_angle_alpha 90.00 _cell_angle_beta 133.986(7) _cell_angle_gamma 90.00 _cell_volume 3032(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2357 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description Platelet _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(Higashi, 1999)' _exptl_absorpt_correction_T_min 0.988 _exptl_absorpt_correction_T_max 0.998 _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.62 _diffrn_reflns_number 12275 _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_sigmaI/netI 0.0873 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3463 _reflns_number_gt 2512 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+19.4000P] 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 3463 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1551 _refine_ls_R_factor_gt 0.1049 _refine_ls_wR_factor_ref 0.2078 _refine_ls_wR_factor_gt 0.1825 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 C21 C 0.5000 0.0558(4) 0.7500 0.0240(11) Uani 1 2 d S . . N1 N 0.37910(18) 0.0921(3) 0.7341(2) 0.0264(7) Uani 1 1 d . . . N2 N 0.32444(18) 0.2705(3) 0.6444(2) 0.0240(7) Uani 1 1 d . . . C1 C 0.5445(2) -0.0273(3) 0.8486(3) 0.0254(8) Uani 1 1 d . . . C2 C 0.5904(2) -0.1311(3) 0.8641(3) 0.0312(9) Uani 1 1 d . . . H2A H 0.5893 -0.1548 0.8118 0.037 Uiso 1 1 calc R . . C3 C 0.6376(2) -0.1996(4) 0.9560(3) 0.0370(10) Uani 1 1 d . . . H3A H 0.6686 -0.2703 0.9659 0.044 Uiso 1 1 calc R . . C4 C 0.6402(3) -0.1669(4) 1.0327(3) 0.0396(10) Uani 1 1 d . . . H4A H 0.6725 -0.2148 1.0951 0.048 Uiso 1 1 calc R . . C5 C 0.5950(2) -0.0629(4) 1.0183(3) 0.0351(9) Uani 1 1 d . . . H5A H 0.5965 -0.0395 1.0709 0.042 Uiso 1 1 calc R . . C6 C 0.5481(2) 0.0064(4) 0.9273(3) 0.0283(8) Uani 1 1 d . . . H6A H 0.5180 0.0778 0.9183 0.034 Uiso 1 1 calc R . . C7 C 0.4293(2) 0.1354(3) 0.7207(3) 0.0239(8) Uani 1 1 d . . . C8 C 0.3169(2) 0.1746(3) 0.6892(3) 0.0241(8) Uani 1 1 d . . . C9 C 0.3965(2) 0.2461(3) 0.6635(3) 0.0237(8) Uani 1 1 d . . . C10 C 0.2718(2) 0.3708(3) 0.5820(3) 0.0261(8) Uani 1 1 d . . . H10A H 0.2221 0.3839 0.5672 0.031 Uiso 1 1 calc R . . C11 C 0.2919(2) 0.4487(4) 0.5431(3) 0.0340(9) Uani 1 1 d . . . H11A H 0.2563 0.5175 0.5008 0.041 Uiso 1 1 calc R . . C12 C 0.3653(2) 0.4300(4) 0.5639(3) 0.0330(9) Uani 1 1 d . . . H12A H 0.3793 0.4877 0.5373 0.040 Uiso 1 1 calc R . . C13 C 0.4158(2) 0.3303(3) 0.6214(3) 0.0282(8) Uani 1 1 d . . . H13A H 0.4642 0.3170 0.6334 0.034 Uiso 1 1 calc R . . C14 C 0.2487(2) 0.1572(4) 0.6834(3) 0.0275(8) Uani 1 1 d . . . C15 C 0.2262(2) 0.0354(4) 0.6840(3) 0.0339(9) Uani 1 1 d . . . H15A H 0.2558 -0.0340 0.6892 0.041 Uiso 1 1 calc R . . C16 C 0.1614(3) 0.0142(4) 0.6773(4) 0.0414(11) Uani 1 1 d . . . H16A H 0.1464 -0.0698 0.6764 0.050 Uiso 1 1 calc R . . C17 C 0.1176(3) 0.1129(4) 0.6717(4) 0.0448(12) Uani 1 1 d . . . C18 C 0.1390(3) 0.2333(4) 0.6711(4) 0.0407(11) Uani 1 1 d . . . H18A H 0.1096 0.3019 0.6671 0.049 Uiso 1 1 calc R . . C19 C 0.2038(2) 0.2564(4) 0.6764(3) 0.0326(9) Uani 1 1 d . . . H19A H 0.2174 0.3405 0.6751 0.039 Uiso 1 1 calc R . . C20 C 0.0468(3) 0.0868(5) 0.6642(6) 0.077(2) Uani 1 1 d . . . H20A H 0.0099 0.1603 0.6347 0.116 Uiso 1 1 calc R . . H20B H 0.0696 0.0695 0.7339 0.116 Uiso 1 1 calc R . . H20C H 0.0149 0.0138 0.6191 0.116 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 C21 0.018(2) 0.022(2) 0.032(3) 0.000 0.018(2) 0.000 N1 0.0207(15) 0.0288(16) 0.0285(17) 0.0012(13) 0.0167(15) 0.0008(12) N2 0.0210(15) 0.0218(14) 0.0250(16) 0.0010(12) 0.0145(14) 0.0021(12) C1 0.0183(17) 0.0254(18) 0.028(2) 0.0004(15) 0.0140(16) -0.0025(14) C2 0.0255(19) 0.0299(19) 0.034(2) 0.0013(16) 0.0193(18) 0.0013(15) C3 0.024(2) 0.032(2) 0.042(2) 0.0079(18) 0.018(2) 0.0038(16) C4 0.030(2) 0.040(2) 0.033(2) 0.0147(19) 0.0167(19) 0.0003(18) C5 0.027(2) 0.045(2) 0.026(2) 0.0044(18) 0.0157(18) -0.0023(17) C6 0.0212(18) 0.0321(19) 0.030(2) -0.0002(16) 0.0172(17) -0.0013(15) C7 0.0220(18) 0.0229(17) 0.0271(19) -0.0004(14) 0.0171(17) -0.0001(14) C8 0.0200(17) 0.0256(17) 0.0244(19) -0.0001(14) 0.0145(16) 0.0019(14) C9 0.0198(16) 0.0238(17) 0.0238(18) -0.0046(14) 0.0138(16) -0.0032(14) C10 0.0217(18) 0.0250(18) 0.0257(19) 0.0034(15) 0.0142(16) 0.0046(14) C11 0.031(2) 0.0286(19) 0.028(2) 0.0030(16) 0.0156(19) 0.0046(16) C12 0.029(2) 0.031(2) 0.030(2) 0.0059(16) 0.0170(19) -0.0028(16) C13 0.0218(18) 0.033(2) 0.028(2) 0.0005(16) 0.0163(17) -0.0011(15) C14 0.0165(17) 0.035(2) 0.0246(19) 0.0044(16) 0.0120(16) 0.0032(15) C15 0.031(2) 0.035(2) 0.036(2) 0.0090(17) 0.024(2) 0.0066(17) C16 0.034(2) 0.036(2) 0.056(3) 0.014(2) 0.032(2) 0.0045(18) C17 0.029(2) 0.050(3) 0.061(3) 0.020(2) 0.033(2) 0.0093(19) C18 0.032(2) 0.045(2) 0.054(3) 0.007(2) 0.034(2) 0.0083(19) C19 0.027(2) 0.034(2) 0.036(2) 0.0017(17) 0.0216(19) 0.0013(16) C20 0.056(3) 0.070(4) 0.132(6) 0.036(4) 0.075(4) 0.019(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C21 C7 1.522(4) . ? C21 C7 1.522(4) 2_656 ? C21 C1 1.560(5) . ? C21 C1 1.560(5) 2_656 ? N1 C8 1.335(4) . ? N1 C7 1.373(5) . ? N2 C8 1.375(5) . ? N2 C10 1.391(4) . ? N2 C9 1.410(5) . ? C1 C6 1.393(5) . ? C1 C2 1.395(5) . ? C2 C3 1.388(6) . ? C2 H2A 0.9500 . ? C3 C4 1.373(6) . ? C3 H3A 0.9500 . ? C4 C5 1.392(6) . ? C4 H4A 0.9500 . ? C5 C6 1.382(5) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C9 1.388(5) . ? C8 C14 1.459(5) . ? C9 C13 1.414(5) . ? C10 C11 1.341(5) . ? C10 H10A 0.9500 . ? C11 C12 1.414(6) . ? C11 H11A 0.9500 . ? C12 C13 1.355(5) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.392(5) . ? C14 C19 1.397(5) . ? C15 C16 1.379(6) . ? C15 H15A 0.9500 . ? C16 C17 1.388(6) . ? C16 H16A 0.9500 . ? C17 C18 1.368(6) . ? C17 C20 1.510(6) . ? C18 C19 1.399(5) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C7 C21 C7 112.4(4) . 2_656 ? C7 C21 C1 113.39(19) . . ? C7 C21 C1 103.46(18) 2_656 . ? C7 C21 C1 103.46(18) . 2_656 ? C7 C21 C1 113.38(19) 2_656 2_656 ? C1 C21 C1 111.0(4) . 2_656 ? C8 N1 C7 107.7(3) . . ? C8 N2 C10 131.2(3) . . ? C8 N2 C9 107.4(3) . . ? C10 N2 C9 121.2(3) . . ? C6 C1 C2 118.7(3) . . ? C6 C1 C21 122.5(3) . . ? C2 C1 C21 118.3(3) . . ? C3 C2 C1 119.9(4) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C5 C6 C1 120.9(4) . . ? C5 C6 H6A 119.6 . . ? C1 C6 H6A 119.6 . . ? N1 C7 C9 109.6(3) . . ? N1 C7 C21 121.6(3) . . ? C9 C7 C21 128.0(3) . . ? N1 C8 N2 110.0(3) . . ? N1 C8 C14 123.5(3) . . ? N2 C8 C14 126.3(3) . . ? C7 C9 N2 105.3(3) . . ? C7 C9 C13 136.7(3) . . ? N2 C9 C13 118.0(3) . . ? C11 C10 N2 119.3(3) . . ? C11 C10 H10A 120.4 . . ? N2 C10 H10A 120.4 . . ? C10 C11 C12 121.1(4) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C13 C12 C11 120.5(4) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C9 119.9(4) . . ? C12 C13 H13A 120.0 . . ? C9 C13 H13A 120.0 . . ? C15 C14 C19 117.7(3) . . ? C15 C14 C8 118.6(3) . . ? C19 C14 C8 123.6(3) . . ? C16 C15 C14 120.8(4) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C15 C16 C17 121.4(4) . . ? C15 C16 H16A 119.3 . . ? C17 C16 H16A 119.3 . . ? C18 C17 C16 118.5(4) . . ? C18 C17 C20 121.2(4) . . ? C16 C17 C20 120.2(4) . . ? C17 C18 C19 120.8(4) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C14 C19 C18 120.8(4) . . ? C14 C19 H19A 119.6 . . ? C18 C19 H19A 119.6 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 C7 C21 C1 C6 -27.8(5) . . . . ? C7 C21 C1 C6 94.3(3) 2_656 . . . ? C1 C21 C1 C6 -143.8(4) 2_656 . . . ? C7 C21 C1 C2 159.9(3) . . . . ? C7 C21 C1 C2 -78.1(4) 2_656 . . . ? C1 C21 C1 C2 43.9(3) 2_656 . . . ? C6 C1 C2 C3 0.9(5) . . . . ? C21 C1 C2 C3 173.5(3) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? C2 C3 C4 C5 -0.3(6) . . . . ? C3 C4 C5 C6 0.0(6) . . . . ? C4 C5 C6 C1 0.8(6) . . . . ? C2 C1 C6 C5 -1.2(5) . . . . ? C21 C1 C6 C5 -173.5(3) . . . . ? C8 N1 C7 C9 -1.6(4) . . . . ? C8 N1 C7 C21 -171.9(3) . . . . ? C7 C21 C7 N1 -152.2(4) 2_656 . . . ? C1 C21 C7 N1 -35.3(4) . . . . ? C1 C21 C7 N1 85.1(4) 2_656 . . . ? C7 C21 C7 C9 39.4(3) 2_656 . . . ? C1 C21 C7 C9 156.3(3) . . . . ? C1 C21 C7 C9 -83.3(4) 2_656 . . . ? C7 N1 C8 N2 1.2(4) . . . . ? C7 N1 C8 C14 177.1(3) . . . . ? C10 N2 C8 N1 173.7(3) . . . . ? C9 N2 C8 N1 -0.4(4) . . . . ? C10 N2 C8 C14 -2.0(6) . . . . ? C9 N2 C8 C14 -176.1(3) . . . . ? N1 C7 C9 N2 1.3(4) . . . . ? C21 C7 C9 N2 170.9(3) . . . . ? N1 C7 C9 C13 -176.6(4) . . . . ? C21 C7 C9 C13 -7.0(7) . . . . ? C8 N2 C9 C7 -0.6(4) . . . . ? C10 N2 C9 C7 -175.4(3) . . . . ? C8 N2 C9 C13 177.8(3) . . . . ? C10 N2 C9 C13 2.9(5) . . . . ? C8 N2 C10 C11 -176.3(4) . . . . ? C9 N2 C10 C11 -2.8(5) . . . . ? N2 C10 C11 C12 0.4(6) . . . . ? C10 C11 C12 C13 1.9(6) . . . . ? C11 C12 C13 C9 -1.8(6) . . . . ? C7 C9 C13 C12 177.1(4) . . . . ? N2 C9 C13 C12 -0.6(5) . . . . ? N1 C8 C14 C15 -27.0(6) . . . . ? N2 C8 C14 C15 148.1(4) . . . . ? N1 C8 C14 C19 153.6(4) . . . . ? N2 C8 C14 C19 -31.3(6) . . . . ? C19 C14 C15 C16 0.4(6) . . . . ? C8 C14 C15 C16 -179.1(4) . . . . ? C14 C15 C16 C17 -1.3(7) . . . . ? C15 C16 C17 C18 1.2(7) . . . . ? C15 C16 C17 C20 179.9(5) . . . . ? C16 C17 C18 C19 -0.2(7) . . . . ? C20 C17 C18 C19 -179.0(5) . . . . ? C15 C14 C19 C18 0.6(6) . . . . ? C8 C14 C19 C18 -180.0(4) . . . . ? C17 C18 C19 C14 -0.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.305 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.050 # Attachment '9732_web_deposit_cif_file_1_ToshiakiMurai_1329874131.en064-2.cif' data_en064-2 _database_code_depnum_ccdc_archive 'CCDC 868372' #TrackingRef '9732_web_deposit_cif_file_1_ToshiakiMurai_1329874131.en064-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 Cl2 N2 O' _chemical_formula_sum 'C28 H22 Cl2 N2 O' _chemical_formula_weight 473.38 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 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 8.513(2) _cell_length_b 23.170(6) _cell_length_c 11.837(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.189(3) _cell_angle_gamma 90.00 _cell_volume 2273.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 6920 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.310 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(Higashi, 1999)' _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.986 _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.62 _diffrn_reflns_number 18043 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5151 _reflns_number_gt 4857 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+2.9790P] 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 0.010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5151 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 O1 O 0.53979(17) 0.27337(6) 0.49365(11) 0.0281(3) Uani 1 1 d . . . H1 H 0.4745 0.2846 0.4346 0.042 Uiso 1 1 calc R . . N1 N 0.31607(17) 0.45017(6) 0.51061(13) 0.0209(3) Uani 1 1 d . . . N2 N 0.34835(18) 0.36567(6) 0.43019(13) 0.0219(3) Uani 1 1 d . . . C1 C 0.5630(2) 0.31766(7) 0.58003(15) 0.0214(4) Uani 1 1 d . . . C2 C 0.7413(2) 0.33447(8) 0.61754(16) 0.0224(4) Uani 1 1 d . . . C3 C 0.8413(2) 0.35468(8) 0.54968(18) 0.0290(4) Uani 1 1 d . . . H3 H 0.8031 0.3592 0.4692 0.035 Uiso 1 1 calc R . . C4 C 1.0006(3) 0.36833(9) 0.6033(2) 0.0352(5) Uani 1 1 d . . . H4 H 1.0706 0.3820 0.5584 0.042 Uiso 1 1 calc R . . C5 C 1.0567(2) 0.36188(9) 0.7223(2) 0.0358(5) Uani 1 1 d . . . H5 H 1.1634 0.3724 0.7571 0.043 Uiso 1 1 calc R . . C6 C 0.9575(2) 0.34016(9) 0.79059(19) 0.0308(4) Uani 1 1 d . . . H6 H 0.9963 0.3352 0.8709 0.037 Uiso 1 1 calc R . . C7 C 0.7992(2) 0.32599(8) 0.73693(16) 0.0236(4) Uani 1 1 d . . . C8 C 0.6688(2) 0.30137(8) 0.78468(15) 0.0226(4) Uani 1 1 d . . . C9 C 0.6649(2) 0.28507(8) 0.89710(16) 0.0275(4) Uani 1 1 d . . . H9 H 0.7572 0.2886 0.9579 0.033 Uiso 1 1 calc R . . C10 C 0.5216(3) 0.26350(9) 0.91756(17) 0.0304(4) Uani 1 1 d . . . H10 H 0.5177 0.2519 0.9929 0.036 Uiso 1 1 calc R . . C11 C 0.3846(2) 0.25886(9) 0.82876(18) 0.0301(4) Uani 1 1 d . . . H11 H 0.2884 0.2448 0.8448 0.036 Uiso 1 1 calc R . . C12 C 0.3880(2) 0.27481(8) 0.71574(17) 0.0258(4) Uani 1 1 d . . . H12 H 0.2951 0.2716 0.6554 0.031 Uiso 1 1 calc R . . C13 C 0.5306(2) 0.29549(7) 0.69437(15) 0.0211(4) Uani 1 1 d . . . C14 C 0.4543(2) 0.36849(7) 0.53525(15) 0.0203(3) Uani 1 1 d . . . C15 C 0.4380(2) 0.42029(8) 0.58919(15) 0.0215(4) Uani 1 1 d . . . C16 C 0.5075(2) 0.44626(9) 0.69734(17) 0.0305(4) Uani 1 1 d . . . H16 H 0.5906 0.4274 0.7504 0.037 Uiso 1 1 calc R . . C17 C 0.4539(3) 0.49850(10) 0.72403(19) 0.0405(5) Uani 1 1 d . . . H17 H 0.5010 0.5162 0.7952 0.049 Uiso 1 1 calc R . . C18 C 0.3259(3) 0.52658(9) 0.64403(19) 0.0392(5) Uani 1 1 d . . . H18 H 0.2875 0.5623 0.6641 0.047 Uiso 1 1 calc R . . C19 C 0.2593(3) 0.50285(8) 0.54038(17) 0.0297(4) Uani 1 1 d . . . H19 H 0.1750 0.5218 0.4886 0.036 Uiso 1 1 calc R . . C20 C 0.2654(2) 0.41509(8) 0.41541(15) 0.0215(4) Uani 1 1 d . . . C21 C 0.1312(2) 0.42686(8) 0.31582(15) 0.0225(4) Uani 1 1 d . . . C22 C 0.0964(2) 0.48100(8) 0.26418(17) 0.0274(4) Uani 1 1 d . . . H22 H 0.1584 0.5132 0.2954 0.033 Uiso 1 1 calc R . . C23 C -0.0293(2) 0.48756(9) 0.16696(18) 0.0313(4) Uani 1 1 d . . . H23 H -0.0517 0.5244 0.1339 0.038 Uiso 1 1 calc R . . C24 C -0.1229(2) 0.44084(9) 0.11753(17) 0.0299(4) Uani 1 1 d . . . C25 C -0.0883(2) 0.38696(9) 0.16939(17) 0.0298(4) Uani 1 1 d . . . H25 H -0.1500 0.3548 0.1375 0.036 Uiso 1 1 calc R . . C26 C 0.0355(2) 0.37996(8) 0.26706(16) 0.0263(4) Uani 1 1 d . . . H26 H 0.0555 0.3433 0.3011 0.032 Uiso 1 1 calc R . . C27 C -0.2582(3) 0.44800(11) 0.0108(2) 0.0462(6) Uani 1 1 d . . . H27 H -0.2948 0.4103 -0.0200 0.069 Uiso 1 1 calc R . . H27A H -0.2195 0.4698 -0.0474 0.069 Uiso 1 1 calc R . . H27B H -0.3471 0.4685 0.0313 0.069 Uiso 1 1 calc R . . C28 C 0.3280(3) 0.32892(12) 0.1309(2) 0.0471(6) Uani 1 1 d . . . H28 H 0.2926 0.2940 0.0855 0.057 Uiso 1 1 calc R . . H28A H 0.2635 0.3326 0.1894 0.057 Uiso 1 1 calc R . . Cl1 Cl 0.53152(8) 0.32186(4) 0.20067(6) 0.0599(2) Uani 1 1 d . . . Cl2 Cl 0.29383(10) 0.38879(3) 0.03922(7) 0.0684(3) 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 O1 0.0333(7) 0.0248(7) 0.0222(6) -0.0050(5) -0.0022(5) 0.0065(5) N1 0.0212(7) 0.0197(7) 0.0209(7) 0.0014(6) 0.0030(6) 0.0011(6) N2 0.0223(7) 0.0224(7) 0.0196(7) 0.0016(6) 0.0015(6) 0.0015(6) C1 0.0228(8) 0.0208(8) 0.0191(8) -0.0010(6) 0.0014(7) 0.0026(7) C2 0.0215(8) 0.0197(8) 0.0256(9) -0.0002(7) 0.0044(7) 0.0043(7) C3 0.0320(10) 0.0251(9) 0.0313(10) 0.0024(8) 0.0104(8) 0.0036(8) C4 0.0296(10) 0.0308(10) 0.0499(13) 0.0019(9) 0.0190(9) -0.0002(8) C5 0.0203(9) 0.0310(10) 0.0537(14) -0.0046(9) 0.0037(9) -0.0003(8) C6 0.0220(9) 0.0324(10) 0.0343(11) -0.0011(8) -0.0015(8) 0.0013(8) C7 0.0213(8) 0.0221(8) 0.0258(9) -0.0007(7) 0.0020(7) 0.0032(7) C8 0.0223(8) 0.0210(8) 0.0226(9) -0.0005(7) 0.0009(7) 0.0027(7) C9 0.0314(10) 0.0272(9) 0.0208(9) -0.0005(7) -0.0005(7) 0.0039(8) C10 0.0414(11) 0.0284(10) 0.0234(9) 0.0021(7) 0.0117(8) 0.0038(8) C11 0.0304(10) 0.0271(9) 0.0356(11) 0.0003(8) 0.0133(8) -0.0006(8) C12 0.0233(9) 0.0238(9) 0.0289(9) -0.0004(7) 0.0031(7) 0.0012(7) C13 0.0222(8) 0.0174(8) 0.0220(8) -0.0002(6) 0.0016(7) 0.0024(6) C14 0.0191(8) 0.0222(8) 0.0184(8) 0.0015(6) 0.0019(6) 0.0007(6) C15 0.0211(8) 0.0217(8) 0.0208(8) 0.0018(7) 0.0027(7) 0.0013(7) C16 0.0339(10) 0.0285(10) 0.0245(9) -0.0021(8) -0.0031(8) 0.0028(8) C17 0.0551(14) 0.0322(11) 0.0274(10) -0.0092(8) -0.0048(10) 0.0052(10) C18 0.0545(14) 0.0267(10) 0.0337(11) -0.0051(8) 0.0044(10) 0.0116(9) C19 0.0353(10) 0.0240(9) 0.0287(10) 0.0004(7) 0.0048(8) 0.0077(8) C20 0.0207(8) 0.0219(8) 0.0211(8) 0.0010(7) 0.0032(7) -0.0004(7) C21 0.0200(8) 0.0256(9) 0.0211(8) 0.0020(7) 0.0029(7) 0.0012(7) C22 0.0264(9) 0.0238(9) 0.0288(10) 0.0027(7) -0.0002(7) -0.0012(7) C23 0.0318(10) 0.0276(10) 0.0311(10) 0.0075(8) -0.0003(8) 0.0043(8) C24 0.0240(9) 0.0366(11) 0.0253(9) 0.0030(8) -0.0020(7) 0.0012(8) C25 0.0282(10) 0.0305(10) 0.0279(10) -0.0017(8) 0.0004(8) -0.0043(8) C26 0.0279(9) 0.0237(9) 0.0258(9) 0.0029(7) 0.0032(7) -0.0003(7) C27 0.0409(13) 0.0509(14) 0.0362(12) 0.0086(10) -0.0134(10) -0.0009(11) C28 0.0372(12) 0.0486(14) 0.0573(16) -0.0007(12) 0.0144(11) 0.0060(10) Cl1 0.0492(4) 0.0885(5) 0.0382(3) -0.0078(3) 0.0020(3) 0.0230(3) Cl2 0.0702(5) 0.0502(4) 0.0696(5) 0.0068(3) -0.0152(4) 0.0038(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.430(2) . ? O1 H1 0.8300 . ? N1 C20 1.376(2) . ? N1 C19 1.388(2) . ? N1 C15 1.407(2) . ? N2 C20 1.336(2) . ? N2 C14 1.361(2) . ? C1 C14 1.517(2) . ? C1 C13 1.530(2) . ? C1 C2 1.531(2) . ? C2 C3 1.379(3) . ? C2 C7 1.400(3) . ? C3 C4 1.396(3) . ? C3 H3 0.9400 . ? C4 C5 1.388(3) . ? C4 H4 0.9400 . ? C5 C6 1.390(3) . ? C5 H5 0.9400 . ? C6 C7 1.392(3) . ? C6 H6 0.9400 . ? C7 C8 1.471(3) . ? C8 C9 1.391(3) . ? C8 C13 1.404(2) . ? C9 C10 1.390(3) . ? C9 H9 0.9400 . ? C10 C11 1.385(3) . ? C10 H10 0.9400 . ? C11 C12 1.395(3) . ? C11 H11 0.9400 . ? C12 C13 1.381(3) . ? C12 H12 0.9400 . ? C14 C15 1.381(2) . ? C15 C16 1.416(3) . ? C16 C17 1.356(3) . ? C16 H16 0.9400 . ? C17 C18 1.427(3) . ? C17 H17 0.9400 . ? C18 C19 1.346(3) . ? C18 H18 0.9400 . ? C19 H19 0.9400 . ? C20 C21 1.468(2) . ? C21 C22 1.397(3) . ? C21 C26 1.401(3) . ? C22 C23 1.389(3) . ? C22 H22 0.9400 . ? C23 C24 1.391(3) . ? C23 H23 0.9400 . ? C24 C25 1.393(3) . ? C24 C27 1.512(3) . ? C25 C26 1.384(3) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C27 H27 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 Cl2 1.745(3) . ? C28 Cl1 1.749(3) . ? C28 H28 0.9800 . ? C28 H28A 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 O1 H1 109.5 . . ? C20 N1 C19 131.70(16) . . ? C20 N1 C15 107.26(14) . . ? C19 N1 C15 120.78(15) . . ? C20 N2 C14 107.38(15) . . ? O1 C1 C14 109.49(14) . . ? O1 C1 C13 111.61(14) . . ? C14 C1 C13 110.54(14) . . ? O1 C1 C2 110.84(14) . . ? C14 C1 C2 112.90(14) . . ? C13 C1 C2 101.28(14) . . ? C3 C2 C7 120.90(17) . . ? C3 C2 C1 128.34(17) . . ? C7 C2 C1 110.75(15) . . ? C2 C3 C4 118.48(19) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 120.71(19) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.01(19) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C7 118.26(19) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C6 C7 C2 120.58(18) . . ? C6 C7 C8 130.79(18) . . ? C2 C7 C8 108.63(15) . . ? C9 C8 C13 120.23(17) . . ? C9 C8 C7 131.11(17) . . ? C13 C8 C7 108.65(16) . . ? C10 C9 C8 118.53(17) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C11 C10 C9 121.11(18) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.61(18) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 118.63(17) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C8 120.87(17) . . ? C12 C13 C1 128.44(16) . . ? C8 C13 C1 110.61(16) . . ? N2 C14 C15 110.41(15) . . ? N2 C14 C1 120.41(15) . . ? C15 C14 C1 129.11(15) . . ? C14 C15 N1 104.98(15) . . ? C14 C15 C16 136.20(17) . . ? N1 C15 C16 118.79(16) . . ? C17 C16 C15 119.76(18) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 119.93(19) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 121.18(19) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 N1 119.49(18) . . ? C18 C19 H19 120.3 . . ? N1 C19 H19 120.3 . . ? N2 C20 N1 109.96(15) . . ? N2 C20 C21 123.76(16) . . ? N1 C20 C21 126.08(16) . . ? C22 C21 C26 118.07(16) . . ? C22 C21 C20 124.53(16) . . ? C26 C21 C20 117.37(16) . . ? C23 C22 C21 120.46(18) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 121.48(18) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C23 C24 C25 117.95(17) . . ? C23 C24 C27 121.32(19) . . ? C25 C24 C27 120.73(19) . . ? C26 C25 C24 121.15(18) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C21 120.89(17) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C24 C27 H27 109.5 . . ? C24 C27 H27A 109.5 . . ? H27 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? Cl2 C28 Cl1 112.00(15) . . ? Cl2 C28 H28 109.2 . . ? Cl1 C28 H28 109.2 . . ? Cl2 C28 H28A 109.2 . . ? Cl1 C28 H28A 109.2 . . ? H28 C28 H28A 107.9 . . ? 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 O1 C1 C2 C3 57.8(2) . . . . ? C14 C1 C2 C3 -65.5(2) . . . . ? C13 C1 C2 C3 176.33(18) . . . . ? O1 C1 C2 C7 -121.31(16) . . . . ? C14 C1 C2 C7 115.44(17) . . . . ? C13 C1 C2 C7 -2.77(18) . . . . ? C7 C2 C3 C4 -2.1(3) . . . . ? C1 C2 C3 C4 178.91(18) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 1.9(3) . . . . ? C4 C5 C6 C7 -1.1(3) . . . . ? C5 C6 C7 C2 -1.1(3) . . . . ? C5 C6 C7 C8 178.49(19) . . . . ? C3 C2 C7 C6 2.8(3) . . . . ? C1 C2 C7 C6 -178.03(17) . . . . ? C3 C2 C7 C8 -176.91(17) . . . . ? C1 C2 C7 C8 2.3(2) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C2 C7 C8 C9 179.71(19) . . . . ? C6 C7 C8 C13 179.65(19) . . . . ? C2 C7 C8 C13 -0.7(2) . . . . ? C13 C8 C9 C10 -0.5(3) . . . . ? C7 C8 C9 C10 179.01(18) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C12 1.2(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C11 C12 C13 C8 -1.1(3) . . . . ? C11 C12 C13 C1 -177.50(17) . . . . ? C9 C8 C13 C12 1.5(3) . . . . ? C7 C8 C13 C12 -178.13(16) . . . . ? C9 C8 C13 C1 178.49(16) . . . . ? C7 C8 C13 C1 -1.2(2) . . . . ? O1 C1 C13 C12 -63.0(2) . . . . ? C14 C1 C13 C12 59.1(2) . . . . ? C2 C1 C13 C12 179.02(18) . . . . ? O1 C1 C13 C8 120.32(16) . . . . ? C14 C1 C13 C8 -117.57(16) . . . . ? C2 C1 C13 C8 2.33(18) . . . . ? C20 N2 C14 C15 0.6(2) . . . . ? C20 N2 C14 C1 177.74(15) . . . . ? O1 C1 C14 N2 3.7(2) . . . . ? C13 C1 C14 N2 -119.61(17) . . . . ? C2 C1 C14 N2 127.75(17) . . . . ? O1 C1 C14 C15 -179.67(17) . . . . ? C13 C1 C14 C15 57.0(2) . . . . ? C2 C1 C14 C15 -55.7(2) . . . . ? N2 C14 C15 N1 -0.6(2) . . . . ? C1 C14 C15 N1 -177.49(17) . . . . ? N2 C14 C15 C16 177.2(2) . . . . ? C1 C14 C15 C16 0.3(4) . . . . ? C20 N1 C15 C14 0.46(19) . . . . ? C19 N1 C15 C14 175.22(16) . . . . ? C20 N1 C15 C16 -177.80(17) . . . . ? C19 N1 C15 C16 -3.0(3) . . . . ? C14 C15 C16 C17 -176.3(2) . . . . ? N1 C15 C16 C17 1.2(3) . . . . ? C15 C16 C17 C18 1.1(4) . . . . ? C16 C17 C18 C19 -1.7(4) . . . . ? C17 C18 C19 N1 -0.1(4) . . . . ? C20 N1 C19 C18 175.7(2) . . . . ? C15 N1 C19 C18 2.4(3) . . . . ? C14 N2 C20 N1 -0.3(2) . . . . ? C14 N2 C20 C21 -175.48(16) . . . . ? C19 N1 C20 N2 -174.10(18) . . . . ? C15 N1 C20 N2 -0.1(2) . . . . ? C19 N1 C20 C21 1.0(3) . . . . ? C15 N1 C20 C21 174.95(17) . . . . ? N2 C20 C21 C22 -145.59(19) . . . . ? N1 C20 C21 C22 40.0(3) . . . . ? N2 C20 C21 C26 32.0(3) . . . . ? N1 C20 C21 C26 -142.39(18) . . . . ? C26 C21 C22 C23 -0.3(3) . . . . ? C20 C21 C22 C23 177.29(18) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? C22 C23 C24 C25 0.8(3) . . . . ? C22 C23 C24 C27 -179.2(2) . . . . ? C23 C24 C25 C26 -0.1(3) . . . . ? C27 C24 C25 C26 179.9(2) . . . . ? C24 C25 C26 C21 -0.9(3) . . . . ? C22 C21 C26 C25 1.1(3) . . . . ? C20 C21 C26 C25 -176.72(18) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.605 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.045 # Attachment '9733_web_deposit_cif_file_2_ToshiakiMurai_1329874131.en091.cif' data_en091 _database_code_depnum_ccdc_archive 'CCDC 868373' #TrackingRef '9733_web_deposit_cif_file_2_ToshiakiMurai_1329874131.en091.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 N4 O' _chemical_formula_sum 'C18 H14 N4 O' _chemical_formula_weight 302.33 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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 n a 21 ' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 25.97(2) _cell_length_b 4.887(4) _cell_length_c 11.168(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1417.7(19) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 4439 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(Higashi, 1999)' _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.989 _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.62 _diffrn_reflns_number 10824 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1684 _reflns_number_gt 1665 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+1.5000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 1684 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 O1 O 0.37652(10) -0.1281(5) 0.2131(2) 0.0357(6) Uani 1 1 d . . . H1 H 0.3693 -0.2617 0.2559 0.054 Uiso 1 1 calc R . . N1 N 0.46996(11) 0.4146(6) 0.2286(3) 0.0359(7) Uani 1 1 d . . . N2 N 0.34739(10) 0.2731(5) 0.5551(2) 0.0250(6) Uani 1 1 d . . . N3 N 0.35048(9) 0.4033(5) 0.3639(2) 0.0228(5) Uani 1 1 d . . . N4 N 0.26462(11) 0.6592(6) 0.5960(3) 0.0344(7) Uani 1 1 d . . . C1 C 0.41111(12) 0.0502(7) 0.2769(3) 0.0270(7) Uani 1 1 d . . . H2 H 0.4394 -0.0619 0.3102 0.032 Uiso 1 1 calc R . . C2 C 0.43373(12) 0.2468(6) 0.1858(3) 0.0274(7) Uani 1 1 d . . . C3 C 0.41946(15) 0.2401(8) 0.0666(3) 0.0400(9) Uani 1 1 d . . . H3 H 0.3937 0.1194 0.0400 0.048 Uiso 1 1 calc R . . C4 C 0.44388(18) 0.4150(10) -0.0127(4) 0.0537(11) Uani 1 1 d . . . H4 H 0.4355 0.4122 -0.0945 0.064 Uiso 1 1 calc R . . C5 C 0.48043(16) 0.5921(9) 0.0298(4) 0.0473(11) Uani 1 1 d . . . H5 H 0.4969 0.7165 -0.0217 0.057 Uiso 1 1 calc R . . C6 C 0.49227(14) 0.5835(8) 0.1487(4) 0.0448(10) Uani 1 1 d . . . H6 H 0.5178 0.7038 0.1769 0.054 Uiso 1 1 calc R . . C7 C 0.38398(11) 0.1909(6) 0.3791(3) 0.0242(6) Uani 1 1 d . . . C8 C 0.38365(12) 0.1071(6) 0.4972(3) 0.0251(6) Uani 1 1 d . . . C9 C 0.41009(13) -0.0935(7) 0.5655(3) 0.0343(8) Uani 1 1 d . . . H7 H 0.4342 -0.2094 0.5285 0.041 Uiso 1 1 calc R . . C10 C 0.40048(15) -0.1168(8) 0.6834(4) 0.0411(9) Uani 1 1 d . . . H8 H 0.4185 -0.2474 0.7289 0.049 Uiso 1 1 calc R . . C11 C 0.36360(15) 0.0530(8) 0.7396(3) 0.0392(9) Uani 1 1 d . . . H9 H 0.3570 0.0330 0.8219 0.047 Uiso 1 1 calc R . . C12 C 0.33763(14) 0.2447(7) 0.6758(3) 0.0339(8) Uani 1 1 d . . . H10 H 0.3132 0.3571 0.7136 0.041 Uiso 1 1 calc R . . C13 C 0.32820(12) 0.4499(6) 0.4687(3) 0.0229(6) Uani 1 1 d . . . C14 C 0.28691(11) 0.6525(6) 0.4886(3) 0.0259(6) Uani 1 1 d . . . C15 C 0.27264(12) 0.8263(6) 0.3954(3) 0.0275(7) Uani 1 1 d . . . H11 H 0.2885 0.8134 0.3200 0.033 Uiso 1 1 calc R . . C16 C 0.23445(13) 1.0184(7) 0.4165(3) 0.0315(7) Uani 1 1 d . . . H12 H 0.2248 1.1428 0.3563 0.038 Uiso 1 1 calc R . . C17 C 0.21076(14) 1.0247(8) 0.5270(3) 0.0369(8) Uani 1 1 d . . . H13 H 0.1843 1.1504 0.5431 0.044 Uiso 1 1 calc R . . C18 C 0.22684(14) 0.8424(8) 0.6133(4) 0.0400(9) Uani 1 1 d . . . H14 H 0.2105 0.8466 0.6884 0.048 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 O1 0.0470(14) 0.0318(12) 0.0284(13) -0.0019(11) 0.0015(11) -0.0055(10) N1 0.0313(14) 0.0381(16) 0.0383(17) -0.0030(14) 0.0038(13) -0.0045(12) N2 0.0292(13) 0.0254(12) 0.0204(13) 0.0008(11) 0.0004(11) -0.0049(10) N3 0.0223(11) 0.0240(11) 0.0222(12) -0.0018(11) 0.0014(11) -0.0005(10) N4 0.0383(15) 0.0392(16) 0.0255(15) -0.0015(13) 0.0094(13) -0.0002(12) C1 0.0292(14) 0.0268(15) 0.0251(16) -0.0010(14) 0.0027(13) 0.0004(13) C2 0.0255(14) 0.0272(15) 0.0294(16) -0.0023(14) 0.0085(13) 0.0056(12) C3 0.046(2) 0.044(2) 0.0302(19) 0.0026(17) -0.0006(16) -0.0087(17) C4 0.064(3) 0.065(3) 0.031(2) 0.014(2) 0.003(2) 0.003(2) C5 0.048(2) 0.042(2) 0.052(3) 0.014(2) 0.023(2) 0.0000(17) C6 0.0344(19) 0.042(2) 0.058(3) -0.0005(19) 0.0173(18) -0.0083(16) C7 0.0254(14) 0.0226(13) 0.0244(15) 0.0033(12) 0.0022(12) -0.0016(11) C8 0.0257(14) 0.0261(14) 0.0235(16) -0.0026(13) -0.0029(13) -0.0031(12) C9 0.0303(16) 0.0345(17) 0.038(2) 0.0041(16) -0.0066(15) -0.0024(14) C10 0.0415(19) 0.0403(19) 0.041(2) 0.0140(18) -0.0141(17) -0.0049(16) C11 0.052(2) 0.045(2) 0.0210(16) 0.0056(15) -0.0053(15) -0.0076(18) C12 0.0420(19) 0.0393(18) 0.0203(15) 0.0013(15) -0.0024(14) -0.0071(15) C13 0.0262(14) 0.0245(14) 0.0179(13) -0.0007(12) -0.0031(11) -0.0016(12) C14 0.0235(14) 0.0265(14) 0.0276(16) -0.0047(13) 0.0013(12) -0.0027(12) C15 0.0275(14) 0.0331(16) 0.0219(15) -0.0005(14) 0.0029(12) 0.0008(13) C16 0.0322(16) 0.0352(17) 0.0271(17) -0.0016(14) -0.0031(14) 0.0009(14) C17 0.0323(17) 0.0400(18) 0.038(2) -0.0076(17) 0.0054(15) 0.0072(15) C18 0.0421(19) 0.050(2) 0.0276(18) -0.0078(18) 0.0138(16) 0.0026(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 O1 C1 1.440(4) . ? O1 H1 0.8300 . ? N1 C2 1.337(4) . ? N1 C6 1.346(5) . ? N2 C12 1.379(4) . ? N2 C13 1.387(4) . ? N2 C8 1.401(4) . ? N3 C13 1.326(4) . ? N3 C7 1.365(4) . ? N4 C14 1.332(4) . ? N4 C18 1.342(4) . ? C1 C7 1.508(4) . ? C1 C2 1.518(4) . ? C1 H2 0.9900 . ? C2 C3 1.381(5) . ? C3 C4 1.385(6) . ? C3 H3 0.9400 . ? C4 C5 1.369(6) . ? C4 H4 0.9400 . ? C5 C6 1.364(6) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 C8 1.381(5) . ? C8 C9 1.419(5) . ? C9 C10 1.345(6) . ? C9 H7 0.9400 . ? C10 C11 1.415(6) . ? C10 H8 0.9400 . ? C11 C12 1.357(5) . ? C11 H9 0.9400 . ? C12 H10 0.9400 . ? C13 C14 1.477(4) . ? C14 C15 1.394(4) . ? C15 C16 1.386(5) . ? C15 H11 0.9400 . ? C16 C17 1.380(5) . ? C16 H12 0.9400 . ? C17 C18 1.377(6) . ? C17 H13 0.9400 . ? C18 H14 0.9400 . ? 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 O1 H1 109.5 . . ? C2 N1 C6 116.3(3) . . ? C12 N2 C13 132.6(3) . . ? C12 N2 C8 121.1(3) . . ? C13 N2 C8 106.4(3) . . ? C13 N3 C7 107.4(3) . . ? C14 N4 C18 117.6(3) . . ? O1 C1 C7 111.0(2) . . ? O1 C1 C2 107.0(3) . . ? C7 C1 C2 113.6(3) . . ? O1 C1 H2 108.3 . . ? C7 C1 H2 108.3 . . ? C2 C1 H2 108.3 . . ? N1 C2 C3 123.2(3) . . ? N1 C2 C1 114.9(3) . . ? C3 C2 C1 121.8(3) . . ? C2 C3 C4 118.6(4) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 119.1(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 118.3(4) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? N1 C6 C5 124.5(4) . . ? N1 C6 H6 117.7 . . ? C5 C6 H6 117.7 . . ? N3 C7 C8 109.9(3) . . ? N3 C7 C1 123.4(3) . . ? C8 C7 C1 126.2(3) . . ? C7 C8 N2 105.8(3) . . ? C7 C8 C9 135.6(3) . . ? N2 C8 C9 118.6(3) . . ? C10 C9 C8 119.6(4) . . ? C10 C9 H7 120.2 . . ? C8 C9 H7 120.2 . . ? C9 C10 C11 120.7(4) . . ? C9 C10 H8 119.7 . . ? C11 C10 H8 119.7 . . ? C12 C11 C10 120.6(3) . . ? C12 C11 H9 119.7 . . ? C10 C11 H9 119.7 . . ? C11 C12 N2 119.5(4) . . ? C11 C12 H10 120.3 . . ? N2 C12 H10 120.3 . . ? N3 C13 N2 110.5(3) . . ? N3 C13 C14 124.4(3) . . ? N2 C13 C14 125.0(3) . . ? N4 C14 C15 122.8(3) . . ? N4 C14 C13 117.9(3) . . ? C15 C14 C13 119.3(3) . . ? C16 C15 C14 118.4(3) . . ? C16 C15 H11 120.8 . . ? C14 C15 H11 120.8 . . ? C17 C16 C15 119.1(3) . . ? C17 C16 H12 120.5 . . ? C15 C16 H12 120.5 . . ? C18 C17 C16 118.5(3) . . ? C18 C17 H13 120.8 . . ? C16 C17 H13 120.8 . . ? N4 C18 C17 123.5(3) . . ? N4 C18 H14 118.2 . . ? C17 C18 H14 118.2 . . ? 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 C6 N1 C2 C3 0.6(5) . . . . ? C6 N1 C2 C1 177.3(3) . . . . ? O1 C1 C2 N1 -175.1(3) . . . . ? C7 C1 C2 N1 62.0(4) . . . . ? O1 C1 C2 C3 1.7(4) . . . . ? C7 C1 C2 C3 -121.3(4) . . . . ? N1 C2 C3 C4 0.2(6) . . . . ? C1 C2 C3 C4 -176.3(3) . . . . ? C2 C3 C4 C5 -1.4(6) . . . . ? C3 C4 C5 C6 1.7(6) . . . . ? C2 N1 C6 C5 -0.2(6) . . . . ? C4 C5 C6 N1 -1.0(7) . . . . ? C13 N3 C7 C8 -1.6(3) . . . . ? C13 N3 C7 C1 170.9(3) . . . . ? O1 C1 C7 N3 -75.4(4) . . . . ? C2 C1 C7 N3 45.3(4) . . . . ? O1 C1 C7 C8 95.8(4) . . . . ? C2 C1 C7 C8 -143.5(3) . . . . ? N3 C7 C8 N2 1.3(3) . . . . ? C1 C7 C8 N2 -170.9(3) . . . . ? N3 C7 C8 C9 -178.6(3) . . . . ? C1 C7 C8 C9 9.2(6) . . . . ? C12 N2 C8 C7 -179.5(3) . . . . ? C13 N2 C8 C7 -0.6(3) . . . . ? C12 N2 C8 C9 0.4(4) . . . . ? C13 N2 C8 C9 179.4(3) . . . . ? C7 C8 C9 C10 178.8(4) . . . . ? N2 C8 C9 C10 -1.0(5) . . . . ? C8 C9 C10 C11 1.2(6) . . . . ? C9 C10 C11 C12 -0.7(6) . . . . ? C10 C11 C12 N2 0.0(5) . . . . ? C13 N2 C12 C11 -178.5(3) . . . . ? C8 N2 C12 C11 0.1(5) . . . . ? C7 N3 C13 N2 1.2(3) . . . . ? C7 N3 C13 C14 -176.0(3) . . . . ? C12 N2 C13 N3 178.4(3) . . . . ? C8 N2 C13 N3 -0.4(3) . . . . ? C12 N2 C13 C14 -4.5(5) . . . . ? C8 N2 C13 C14 176.7(3) . . . . ? C18 N4 C14 C15 0.1(5) . . . . ? C18 N4 C14 C13 -179.5(3) . . . . ? N3 C13 C14 N4 173.6(3) . . . . ? N2 C13 C14 N4 -3.1(5) . . . . ? N3 C13 C14 C15 -5.9(5) . . . . ? N2 C13 C14 C15 177.3(3) . . . . ? N4 C14 C15 C16 1.6(5) . . . . ? C13 C14 C15 C16 -178.9(3) . . . . ? C14 C15 C16 C17 -2.3(5) . . . . ? C15 C16 C17 C18 1.3(5) . . . . ? C14 N4 C18 C17 -1.1(5) . . . . ? C16 C17 C18 N4 0.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.372 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.043