# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 loop_ _publ_author_name _publ_author_address G.Jayamurugan ;Laboratory for Organic Chemistry, ETH Zurich, H-8093 Zurich, Switzerland ; P.Gisselbrecht ;Laboratoire d\'Electrochimie et de Chimie Physique du corps solide, UMR 7512, C.N.R.S., Universit\'e Louis Pasteur, 4, rue Blaise Pascal, 67000 Strasbourg, France. ; C.Boudon ;Laboratoire d\'Electrochimie et de Chimie Physique du corps solide, UMR 7512, C.N.R.S., Universit\'e Louis Pasteur, 4, rue Blaise Pascal, 67000 Strasbourg, France. ; F.Schoenebeck ;Laboratory for Organic Chemistry, ETH Zurich, H-8093 Zurich, Switzerland ; W.B.Schweizer ;Laboratory for Organic Chemistry, ETH Zurich, H-8093 Zurich, Switzerland ; B.Bernet ;Laboratory for Organic Chemistry, ETH Zurich, H-8093 Zurich, Switzerland ; F.Diederich ;Laboratory for Organic Chemistry, ETH Zurich, H-8093 Zurich, Switzerland ; _audit_creation_method maXus _publ_section_title ; Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalized 6,6-dicyanofulvene with an intense, low-energy charge-transfer band; ; _publ_contact_author_email diederich@org.chem.ethz.ch _publ_contact_author_name F.Diederich data_5 _database_code_depnum_ccdc_archive 'CCDC 801743' #TrackingRef '- JJdeposit.cif' _chemical_compound_source 'LOC ETH Zurich' _exptl_crystal_description plate _exptl_crystal_size_max .33 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .03 _exptl_crystal_F_000 1856.0 _exptl_crystal_colour amber _diffrn_ambient_temperature 100 _cell_measurement_temperature 100 _refine_ls_hydrogen_treatment refall # Submission details _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.07604 _diffrn_orient_matrix_UB_12 0.00970 _diffrn_orient_matrix_UB_13 -0.04434 _diffrn_orient_matrix_UB_21 -0.01541 _diffrn_orient_matrix_UB_22 -0.05058 _diffrn_orient_matrix_UB_23 -0.03749 _diffrn_orient_matrix_UB_31 -0.01793 _diffrn_orient_matrix_UB_32 0.02431 _diffrn_orient_matrix_UB_33 -0.02543 _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 443.514 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,+Y,-Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X+ 1/2,+Y+ 1/2,+Z' '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P b c a ' _symmetry_cell_setting Orthorhombic _chemical_formula_moiety 'C27 H21 N7 ' _chemical_formula_sum 'C27 H21 N7 ' _chemical_name_systematic ; ? ; _cell_length_a 11.2924(4) _cell_length_b 15.4265(7) _cell_length_c 25.3239(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4411.5(3) _diffrn_reflns_av_R_equivalents 0.093 _diffrn_reflns_number 7442 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_full 25.03 _cell_measurement_reflns_used 356500 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_absorpt_coefficient_mu 0.084 _reflns_number_total 3818 _reflns_number_gt 3026 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3818 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.249 _refine_ls_restrained_S_all 1.249 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.002 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 N12 N 0.1099(2) 0.21444(16) 0.14920(10) 0.0246(6) Uani 1 1 d . . . N21 N 0.1009(3) 0.4547(2) 0.24343(11) 0.0441(8) Uani 1 1 d . . . N25 N 0.2111(2) 0.61503(18) -0.10248(11) 0.0328(7) Uani 1 1 d . . . N27 N 0.5101(2) 0.44471(16) -0.09506(10) 0.0281(6) Uani 1 1 d . . . N29 N 0.2411(2) 0.38205(19) -0.18602(11) 0.0344(7) Uani 1 1 d . . . N32 N -0.0062(2) 0.26986(18) -0.17103(11) 0.0347(7) Uani 1 1 d . . . N34 N 0.0216(2) 0.13239(17) -0.02652(11) 0.0284(6) Uani 1 1 d . . . C1 C 0.1640(2) 0.33734(18) 0.00539(11) 0.0213(6) Uani 1 1 d . . . C2 C 0.2215(2) 0.42304(18) 0.02691(11) 0.0212(6) Uani 1 1 d . . . C3 C 0.2806(2) 0.4775(2) -0.00296(11) 0.0232(7) Uani 1 1 d . . . C4 C 0.2911(2) 0.46905(19) -0.06255(11) 0.0225(6) Uani 1 1 d . . . C5 C 0.2187(2) 0.39364(19) -0.08509(11) 0.0226(6) Uani 1 1 d . . . C6 C 0.1552(2) 0.33633(18) -0.05515(11) 0.0217(6) Uani 1 1 d . . . C7 C 0.2437(2) 0.26517(18) 0.02441(12) 0.0216(6) Uani 1 1 d . . . C8 C 0.2229(2) 0.21956(19) 0.06820(12) 0.0233(6) Uani 1 1 d . . . C9 C 0.1177(2) 0.23816(18) 0.09978(11) 0.0228(6) Uani 1 1 d . . . C10 C 0.0223(2) 0.28503(19) 0.07409(12) 0.0239(7) Uani 1 1 d . . . C11 C 0.0431(2) 0.33003(18) 0.03011(12) 0.0230(6) Uani 1 1 d . . . C13 C 0.2008(3) 0.1600(2) 0.17438(14) 0.0330(8) Uani 1 1 d . . . C14 C 0.0087(3) 0.2398(2) 0.18286(13) 0.0307(7) Uani 1 1 d . . . C15 C 0.2039(2) 0.44014(18) 0.08433(12) 0.0219(6) Uani 1 1 d . . . C16 C 0.2737(3) 0.40312(19) 0.12341(12) 0.0261(7) Uani 1 1 d . . . C17 C 0.2417(3) 0.4096(2) 0.17635(13) 0.0318(7) Uani 1 1 d . . . C18 C 0.1390(3) 0.4541(2) 0.19197(13) 0.0315(7) Uani 1 1 d . . . C19 C 0.0751(3) 0.4984(2) 0.15287(13) 0.0315(7) Uani 1 1 d . . . C20 C 0.1065(3) 0.48962(19) 0.10040(12) 0.0265(7) Uani 1 1 d . . . C22 C 0.1653(4) 0.4091(3) 0.28340(15) 0.0473(10) Uani 1 1 d . . . C23 C 0.0091(3) 0.5156(3) 0.25935(16) 0.0502(10) Uani 1 1 d . . . C24 C 0.2486(2) 0.5517(2) -0.08538(12) 0.0242(7) Uani 1 1 d . . . C26 C 0.4170(2) 0.45721(18) -0.07919(11) 0.0214(6) Uani 1 1 d . . . C28 C 0.2270(2) 0.38618(19) -0.14097(12) 0.0246(7) Uani 1 1 d . . . C30 C 0.0805(2) 0.27103(19) -0.07680(11) 0.0224(6) Uani 1 1 d . . . C31 C 0.0360(2) 0.27141(19) -0.12937(12) 0.0252(7) Uani 1 1 d . . . C33 C 0.0487(2) 0.19572(19) -0.04804(12) 0.0224(6) Uani 1 1 d . . . H3 H 0.317(3) 0.529(2) 0.0140(14) 0.036(9) Uiso 1 1 d . . . H7 H 0.311(3) 0.258(2) 0.0066(13) 0.026(8) Uiso 1 1 d . . . H8 H 0.279(3) 0.178(2) 0.0818(13) 0.023(8) Uiso 1 1 d . . . H10 H -0.063(3) 0.289(2) 0.0902(13) 0.026(8) Uiso 1 1 d . . . H11 H -0.013(3) 0.364(2) 0.0138(13) 0.023(8) Uiso 1 1 d . . . H13A H 0.277(3) 0.185(2) 0.1703(13) 0.031(9) Uiso 1 1 d . . . H13B H 0.211(4) 0.097(4) 0.153(2) 0.083(15) Uiso 1 1 d . . . H13C H 0.182(4) 0.155(3) 0.213(2) 0.065(13) Uiso 1 1 d . . . H14A H -0.027(3) 0.293(3) 0.1724(16) 0.044(10) Uiso 1 1 d . . . H14B H 0.037(4) 0.239(3) 0.222(2) 0.064(12) Uiso 1 1 d . . . H14C H -0.058(3) 0.195(2) 0.1772(14) 0.041(9) Uiso 1 1 d . . . H16 H 0.347(3) 0.370(2) 0.1128(14) 0.034(9) Uiso 1 1 d . . . H17 H 0.291(3) 0.378(2) 0.2019(15) 0.037(9) Uiso 1 1 d . . . H19 H 0.000(3) 0.532(2) 0.1640(15) 0.041(9) Uiso 1 1 d . . . H20 H 0.059(3) 0.521(2) 0.0711(16) 0.047(10) Uiso 1 1 d . . . H22A H 0.249(4) 0.425(3) 0.2882(17) 0.059(12) Uiso 1 1 d . . . H22B H 0.204(3) 0.354(3) 0.2728(14) 0.031(9) Uiso 1 1 d . . . H22C H 0.108(6) 0.419(4) 0.322(3) 0.13(2) Uiso 1 1 d . . . H23A H -0.070(4) 0.503(3) 0.2404(18) 0.065(13) Uiso 1 1 d . . . H23B H 0.036(3) 0.581(3) 0.2538(16) 0.052(11) Uiso 1 1 d . . . H23C H -0.005(4) 0.510(3) 0.299(2) 0.063(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N12 0.0260(12) 0.0226(13) 0.0251(14) 0.0010(10) 0.0002(10) -0.0062(10) N21 0.0585(19) 0.0489(19) 0.0249(15) -0.0027(13) 0.0054(13) -0.0049(15) N25 0.0273(13) 0.0321(17) 0.0391(16) 0.0033(13) 0.0032(11) 0.0031(11) N27 0.0298(14) 0.0264(15) 0.0280(14) -0.0002(11) 0.0007(11) 0.0015(10) N29 0.0317(14) 0.0430(18) 0.0284(16) 0.0014(12) 0.0036(11) -0.0025(12) N32 0.0326(14) 0.0385(17) 0.0330(17) -0.0014(12) -0.0022(12) -0.0019(12) N34 0.0294(13) 0.0246(15) 0.0310(15) -0.0002(12) -0.0014(11) -0.0020(10) C1 0.0221(13) 0.0207(16) 0.0212(15) -0.0010(12) 0.0009(11) -0.0004(11) C2 0.0192(13) 0.0187(15) 0.0258(16) -0.0015(11) -0.0015(11) 0.0039(11) C3 0.0221(14) 0.0246(17) 0.0230(16) -0.0043(12) 0.0020(11) -0.0004(12) C4 0.0222(14) 0.0234(16) 0.0219(15) 0.0012(12) 0.0019(11) 0.0004(11) C5 0.0232(14) 0.0221(16) 0.0226(15) -0.0008(12) 0.0002(11) 0.0006(11) C6 0.0213(13) 0.0187(15) 0.0250(15) -0.0016(12) 0.0016(11) 0.0044(11) C7 0.0202(14) 0.0191(16) 0.0255(15) -0.0037(12) 0.0004(12) -0.0002(11) C8 0.0234(14) 0.0200(16) 0.0263(16) -0.0024(12) -0.0047(12) -0.0006(12) C9 0.0242(14) 0.0173(15) 0.0267(17) -0.0019(12) 0.0013(12) -0.0044(11) C10 0.0229(15) 0.0224(16) 0.0264(16) -0.0026(12) 0.0033(12) -0.0008(11) C11 0.0214(14) 0.0193(16) 0.0282(16) 0.0004(12) -0.0015(12) 0.0000(12) C13 0.0277(17) 0.044(2) 0.0269(18) 0.0085(15) -0.0030(13) -0.0034(15) C14 0.0301(16) 0.038(2) 0.0242(18) 0.0023(14) 0.0054(13) -0.0016(15) C15 0.0248(14) 0.0163(15) 0.0247(16) -0.0012(11) 0.0010(11) -0.0036(11) C16 0.0290(16) 0.0183(16) 0.0308(17) -0.0034(12) -0.0027(13) -0.0031(12) C17 0.0457(18) 0.0227(17) 0.0269(17) -0.0014(13) -0.0100(14) -0.0046(14) C18 0.0434(18) 0.0256(17) 0.0256(17) -0.0047(13) 0.0075(13) -0.0095(14) C19 0.0322(16) 0.0311(18) 0.0313(18) -0.0067(14) 0.0039(14) -0.0041(14) C20 0.0304(16) 0.0241(17) 0.0249(17) -0.0029(13) 0.0017(13) -0.0009(12) C22 0.057(2) 0.053(3) 0.032(2) -0.0019(18) -0.0026(17) -0.016(2) C23 0.046(2) 0.072(3) 0.032(2) -0.0166(19) 0.0101(17) -0.011(2) C24 0.0206(14) 0.0241(17) 0.0279(16) 0.0001(12) 0.0033(12) -0.0002(12) C26 0.0259(15) 0.0162(15) 0.0221(15) -0.0015(11) -0.0002(12) -0.0008(11) C28 0.0209(14) 0.0229(16) 0.0301(18) 0.0006(12) 0.0001(12) -0.0013(12) C30 0.0237(14) 0.0204(16) 0.0232(15) -0.0009(12) 0.0010(11) 0.0017(11) C31 0.0223(14) 0.0239(17) 0.0293(18) -0.0029(13) 0.0010(13) -0.0017(11) C33 0.0201(13) 0.0214(16) 0.0257(16) -0.0042(13) -0.0028(11) 0.0000(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N12 C9 1.307(4) . ? N12 C13 1.471(4) . ? N12 C14 1.479(4) . ? N21 C18 1.372(4) . ? N21 C22 1.431(5) . ? N21 C23 1.456(5) . ? N25 C24 1.149(4) . ? N27 C26 1.142(4) . ? N29 C28 1.154(4) . ? N32 C31 1.158(4) . ? N34 C33 1.160(4) . ? C1 C11 1.506(4) . ? C1 C7 1.510(4) . ? C1 C6 1.536(4) . ? C1 C2 1.570(4) . ? C2 C3 1.313(4) . ? C2 C15 1.491(4) . ? C3 C4 1.519(4) . ? C4 C24 1.481(4) . ? C4 C26 1.493(4) . ? C4 C5 1.532(4) . ? C5 C6 1.368(4) . ? C5 C28 1.423(4) . ? C6 C30 1.424(4) . ? C7 C8 1.334(4) . ? C8 C9 1.461(4) . ? C9 C10 1.451(4) . ? C10 C11 1.333(4) . ? C15 C16 1.388(4) . ? C15 C20 1.399(4) . ? C16 C17 1.392(5) . ? C17 C18 1.404(5) . ? C18 C19 1.403(5) . ? C19 C20 1.382(4) . ? C30 C33 1.417(4) . ? C30 C31 1.423(4) . ? C3 H3 0.99(4) . ? C7 H7 0.89(3) . ? C8 H8 0.97(3) . ? C10 H10 1.04(3) . ? C11 H11 0.92(3) . ? C13 H13A 0.95(3) . ? C13 H13B 1.11(5) . ? C13 H13C 1.01(5) . ? C14 H14A 0.96(4) . ? C14 H14B 1.05(5) . ? C14 H14C 1.03(4) . ? C16 H16 1.01(3) . ? C17 H17 0.99(4) . ? C19 H19 1.04(4) . ? C20 H20 1.04(4) . ? C22 H22A 0.98(5) . ? C22 H22B 0.99(4) . ? C22 H22C 1.18(7) . ? C23 H23A 1.03(5) . ? C23 H23B 1.07(4) . ? C23 H23C 1.02(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N12 C13 121.9(3) . . ? C9 N12 C14 122.0(3) . . ? C13 N12 C14 116.1(3) . . ? C18 N21 C22 120.6(3) . . ? C18 N21 C23 119.4(3) . . ? C22 N21 C23 118.9(3) . . ? C11 C1 C7 110.6(2) . . ? C11 C1 C6 110.8(2) . . ? C7 C1 C6 110.5(2) . . ? C11 C1 C2 107.1(2) . . ? C7 C1 C2 105.3(2) . . ? C6 C1 C2 112.4(2) . . ? C3 C2 C15 121.1(3) . . ? C3 C2 C1 123.3(3) . . ? C15 C2 C1 115.6(2) . . ? C2 C3 C4 123.8(3) . . ? C24 C4 C26 107.7(2) . . ? C24 C4 C3 106.8(2) . . ? C26 C4 C3 111.4(2) . . ? C24 C4 C5 109.6(2) . . ? C26 C4 C5 108.0(2) . . ? C3 C4 C5 113.2(2) . . ? C6 C5 C28 122.2(3) . . ? C6 C5 C4 124.3(3) . . ? C28 C5 C4 113.4(2) . . ? C5 C6 C30 123.7(3) . . ? C5 C6 C1 120.8(3) . . ? C30 C6 C1 115.5(2) . . ? C8 C7 C1 123.3(3) . . ? C7 C8 C9 119.6(3) . . ? N12 C9 C10 121.3(3) . . ? N12 C9 C8 121.6(3) . . ? C10 C9 C8 117.1(3) . . ? C11 C10 C9 120.2(3) . . ? C10 C11 C1 123.1(3) . . ? C16 C15 C20 117.6(3) . . ? C16 C15 C2 123.2(3) . . ? C20 C15 C2 119.0(3) . . ? C15 C16 C17 120.7(3) . . ? C16 C17 C18 121.4(3) . . ? N21 C18 C17 122.0(3) . . ? N21 C18 C19 120.4(3) . . ? C17 C18 C19 117.6(3) . . ? C20 C19 C18 120.0(3) . . ? C19 C20 C15 122.3(3) . . ? N25 C24 C4 177.2(3) . . ? N27 C26 C4 174.9(3) . . ? N29 C28 C5 175.5(3) . . ? C33 C30 C31 113.3(2) . . ? C33 C30 C6 122.1(3) . . ? C31 C30 C6 124.5(3) . . ? N32 C31 C30 176.1(3) . . ? N34 C33 C30 177.1(3) . . ? C2 C3 H3 118(2) . . ? C4 C3 H3 118(2) . . ? C8 C7 H7 120(2) . . ? C1 C7 H7 116(2) . . ? C7 C8 H8 122.0(18) . . ? C9 C8 H8 118.1(19) . . ? C11 C10 H10 117.2(17) . . ? C9 C10 H10 122.5(18) . . ? C10 C11 H11 123.1(19) . . ? C1 C11 H11 113.5(19) . . ? N12 C13 H13A 111(2) . . ? N12 C13 H13B 111(3) . . ? H13A C13 H13B 102(3) . . ? N12 C13 H13C 109(2) . . ? H13A C13 H13C 109(3) . . ? H13B C13 H13C 115(4) . . ? N12 C14 H14A 113(2) . . ? N12 C14 H14B 108(2) . . ? H14A C14 H14B 114(3) . . ? N12 C14 H14C 108(2) . . ? H14A C14 H14C 103(3) . . ? H14B C14 H14C 110(3) . . ? C15 C16 H16 119(2) . . ? C17 C16 H16 120(2) . . ? C16 C17 H17 117(2) . . ? C18 C17 H17 122(2) . . ? C20 C19 H19 121(2) . . ? C18 C19 H19 118(2) . . ? C19 C20 H20 121(2) . . ? C15 C20 H20 117(2) . . ? N21 C22 H22A 117(3) . . ? N21 C22 H22B 117(2) . . ? H22A C22 H22B 79(3) . . ? N21 C22 H22C 104(3) . . ? H22A C22 H22C 113(4) . . ? H22B C22 H22C 125(4) . . ? N21 C23 H23A 111(2) . . ? N21 C23 H23B 112(2) . . ? H23A C23 H23B 111(3) . . ? N21 C23 H23C 109(2) . . ? H23A C23 H23C 108(4) . . ? H23B C23 H23C 105(3) . . ? 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 C11 C1 C2 C3 -137.3(3) . . . . ? C7 C1 C2 C3 104.9(3) . . . . ? C6 C1 C2 C3 -15.4(4) . . . . ? C11 C1 C2 C15 42.1(3) . . . . ? C7 C1 C2 C15 -75.7(3) . . . . ? C6 C1 C2 C15 164.0(2) . . . . ? C15 C2 C3 C4 -173.4(2) . . . . ? C1 C2 C3 C4 6.0(4) . . . . ? C2 C3 C4 C24 124.5(3) . . . . ? C2 C3 C4 C26 -118.2(3) . . . . ? C2 C3 C4 C5 3.8(4) . . . . ? C24 C4 C5 C6 -122.1(3) . . . . ? C26 C4 C5 C6 120.8(3) . . . . ? C3 C4 C5 C6 -3.0(4) . . . . ? C24 C4 C5 C28 60.1(3) . . . . ? C26 C4 C5 C28 -57.0(3) . . . . ? C3 C4 C5 C28 179.2(2) . . . . ? C28 C5 C6 C30 -7.9(4) . . . . ? C4 C5 C6 C30 174.6(3) . . . . ? C28 C5 C6 C1 170.2(3) . . . . ? C4 C5 C6 C1 -7.4(4) . . . . ? C11 C1 C6 C5 135.5(3) . . . . ? C7 C1 C6 C5 -101.6(3) . . . . ? C2 C1 C6 C5 15.7(4) . . . . ? C11 C1 C6 C30 -46.4(3) . . . . ? C7 C1 C6 C30 76.6(3) . . . . ? C2 C1 C6 C30 -166.1(2) . . . . ? C11 C1 C7 C8 -19.4(4) . . . . ? C6 C1 C7 C8 -142.4(3) . . . . ? C2 C1 C7 C8 95.9(3) . . . . ? C1 C7 C8 C9 0.8(4) . . . . ? C13 N12 C9 C10 174.2(3) . . . . ? C14 N12 C9 C10 -5.0(4) . . . . ? C13 N12 C9 C8 -6.4(4) . . . . ? C14 N12 C9 C8 174.4(3) . . . . ? C7 C8 C9 N12 -160.1(3) . . . . ? C7 C8 C9 C10 19.2(4) . . . . ? N12 C9 C10 C11 160.5(3) . . . . ? C8 C9 C10 C11 -18.8(4) . . . . ? C9 C10 C11 C1 -1.7(4) . . . . ? C7 C1 C11 C10 19.8(4) . . . . ? C6 C1 C11 C10 142.7(3) . . . . ? C2 C1 C11 C10 -94.4(3) . . . . ? C3 C2 C15 C16 -98.3(4) . . . . ? C1 C2 C15 C16 82.3(3) . . . . ? C3 C2 C15 C20 87.5(3) . . . . ? C1 C2 C15 C20 -91.9(3) . . . . ? C20 C15 C16 C17 5.0(4) . . . . ? C2 C15 C16 C17 -169.3(3) . . . . ? C15 C16 C17 C18 -0.6(5) . . . . ? C22 N21 C18 C17 -0.1(5) . . . . ? C23 N21 C18 C17 167.5(3) . . . . ? C22 N21 C18 C19 179.5(3) . . . . ? C23 N21 C18 C19 -12.8(5) . . . . ? C16 C17 C18 N21 174.3(3) . . . . ? C16 C17 C18 C19 -5.4(4) . . . . ? N21 C18 C19 C20 -172.8(3) . . . . ? C17 C18 C19 C20 6.8(5) . . . . ? C18 C19 C20 C15 -2.4(5) . . . . ? C16 C15 C20 C19 -3.6(4) . . . . ? C2 C15 C20 C19 171.0(3) . . . . ? C26 C4 C24 N25 170(7) . . . . ? C3 C4 C24 N25 -70(7) . . . . ? C5 C4 C24 N25 53(7) . . . . ? C24 C4 C26 N27 -93(4) . . . . ? C3 C4 C26 N27 150(3) . . . . ? C5 C4 C26 N27 26(4) . . . . ? C6 C5 C28 N29 -144(4) . . . . ? C4 C5 C28 N29 34(4) . . . . ? C5 C6 C30 C33 157.8(3) . . . . ? C1 C6 C30 C33 -20.3(4) . . . . ? C5 C6 C30 C31 -18.5(4) . . . . ? C1 C6 C30 C31 163.4(3) . . . . ? C33 C30 C31 N32 42(5) . . . . ? C6 C30 C31 N32 -142(5) . . . . ? C31 C30 C33 N34 18(6) . . . . ? C6 C30 C33 N34 -159(6) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.222 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.059 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_6 _database_code_depnum_ccdc_archive 'CCDC 801744' #TrackingRef '- JJdeposit.cif' _publ_section_comment ; One disordered chloroform close to inversion centre in unit cell. Two positions refined. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _chemical_compound_source 'LOC ETH Zurich' _exptl_crystal_description Cube _exptl_crystal_size_max .27 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .21 _exptl_crystal_F_000 494.0 _exptl_crystal_colour black _diffrn_ambient_temperature 100 _cell_measurement_temperature 100 _refine_ls_hydrogen_treatment constr # Submission details _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 -0.04066 _diffrn_orient_matrix_UB_12 -0.09817 _diffrn_orient_matrix_UB_13 0.03879 _diffrn_orient_matrix_UB_21 0.00936 _diffrn_orient_matrix_UB_22 -0.05970 _diffrn_orient_matrix_UB_23 -0.07264 _diffrn_orient_matrix_UB_31 0.07500 _diffrn_orient_matrix_UB_32 -0.03233 _diffrn_orient_matrix_UB_33 0.01220 _cell_formula_units_Z 1 _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 868.312 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z _symmetry_space_group_name_H-M 'P -1 ' _symmetry_cell_setting Triclinic _chemical_formula_moiety '2(C26 H20 N6), C H Cl3 ' _chemical_formula_sum 'C53 H41 Cl3 N6 ' _chemical_name_systematic ; ? ; _cell_length_a 9.1282(3) _cell_length_b 11.1896(3) _cell_length_c 12.4251(4) _cell_angle_alpha 102.4170(13) _cell_angle_beta 90.4984(13) _cell_angle_gamma 103.9678(13) _cell_volume 1200.32(6) _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_number 9624 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_full 27.52 _cell_measurement_reflns_used 31360 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' Cl Cl 0.1484 0.1585 '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' _exptl_absorpt_coefficient_mu 0.242 _reflns_number_total 5472 _reflns_number_gt 4453 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5472 _refine_ls_number_parameters 328 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2329 _refine_ls_wR_factor_gt 0.2208 _refine_ls_goodness_of_fit_ref 1.710 _refine_ls_restrained_S_all 3.537 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 Cl34 Cl 0.4802(7) 0.8500(8) 0.0077(6) 0.092(3) Uani 0.369(5) 1 d PD . 1 Cl35 Cl 0.7421(6) 1.0206(4) -0.0005(4) 0.0653(16) Uani 0.369(5) 1 d PD . 1 Cl36 Cl 0.5372(11) 1.1225(10) -0.0411(7) 0.196(12) Uani 0.369(5) 1 d PD . 1 N17 N 0.7862(5) 0.3679(4) 0.8438(3) 0.0369(10) Uani 1 1 d . . . N18 N 0.3789(5) 0.4833(5) 0.8836(3) 0.0407(11) Uani 1 1 d . . . N19 N 0.6196(5) 0.1271(4) 0.2770(3) 0.0340(9) Uani 1 1 d . . . N20 N 0.2352(4) 0.5273(4) 0.6473(3) 0.0309(9) Uani 1 1 d . . . N21 N 1.0425(4) 0.0466(4) 0.6769(4) 0.0404(11) Uani 1 1 d . . . N30 N 0.0337(4) 0.3299(4) 0.0931(3) 0.0264(9) Uani 1 1 d . . . C1 C 0.5063(4) 0.3408(4) 0.6309(4) 0.0233(9) Uani 1 1 d . . . C2 C 0.5870(4) 0.2652(4) 0.5513(3) 0.0229(9) Uani 1 1 d . . . C3 C 0.5291(5) 0.2595(4) 0.4478(4) 0.0235(9) Uani 1 1 d . . . C4 C 0.4057(4) 0.3249(4) 0.4540(3) 0.0227(9) Uani 1 1 d . . . C5 C 0.3952(4) 0.3724(4) 0.5674(3) 0.0226(9) Uani 1 1 d . . . C6 C 0.5419(5) 0.3771(4) 0.7431(4) 0.0251(9) Uani 1 1 d . . . C7 C 0.6777(5) 0.3670(4) 0.7954(4) 0.0277(10) Uani 1 1 d . . . C8 C 0.4505(5) 0.4377(5) 0.8191(4) 0.0294(10) Uani 1 1 d . . . C9 C 0.5773(5) 0.1870(4) 0.3520(4) 0.0254(9) Uani 1 1 d . . . C10 C 0.3062(5) 0.4566(4) 0.6130(3) 0.0235(9) Uani 1 1 d . . . C11 C 0.7025(5) 0.2047(4) 0.5801(4) 0.0241(9) Uani 1 1 d . . . C12 C 0.8475(5) 0.2315(5) 0.5400(4) 0.0311(10) Uani 1 1 d . . . C13 C 0.9594(5) 0.1805(5) 0.5721(4) 0.0338(11) Uani 1 1 d . . . C14 C 0.9304(5) 0.0953(4) 0.6435(4) 0.0301(10) Uani 1 1 d . . . C15 C 0.7822(5) 0.0638(4) 0.6782(4) 0.0283(10) Uani 1 1 d . . . C16 C 0.6728(5) 0.1183(4) 0.6482(4) 0.0267(9) Uani 1 1 d . . . C22 C 1.0115(6) -0.0391(5) 0.7509(4) 0.0356(11) Uani 1 1 d . . . C23 C 1.1991(5) 0.0958(5) 0.6545(6) 0.0484(15) Uani 1 1 d . . . C24 C 0.3169(4) 0.3331(4) 0.3624(3) 0.0219(9) Uani 1 1 d . . . C25 C 0.1788(5) 0.3721(4) 0.3765(4) 0.0244(9) Uani 1 1 d . . . C26 C 0.0875(5) 0.3741(4) 0.2899(4) 0.0243(9) Uani 1 1 d . . . C27 C 0.1261(5) 0.3354(4) 0.1793(3) 0.0230(9) Uani 1 1 d . . . C28 C 0.2681(5) 0.3022(4) 0.1637(3) 0.0255(9) Uani 1 1 d . . . C29 C 0.3583(5) 0.3014(4) 0.2515(3) 0.0245(9) Uani 1 1 d . . . C31 C 0.0721(6) 0.2890(5) -0.0208(4) 0.0346(11) Uani 1 1 d . . . C32 C -0.1050(5) 0.3741(5) 0.1109(4) 0.0335(11) Uani 1 1 d . . . C33 C 0.5546(18) 0.9897(12) -0.0362(13) 0.18(2) Uiso 0.369(5) 1 d PD . 1 Cl38 Cl 0.3499(18) 0.9534(12) 0.0499(13) 0.083(5) Uiso 0.131(5) 1 d PRD . 2 Cl39 Cl 0.6278(18) 0.9673(12) -0.0225(13) 0.152(12) Uiso 0.131(5) 1 d PRD . 2 Cl40 Cl 0.5429(18) 0.8578(12) 0.0752(13) 0.150 Uiso 0.131(5) 1 d PRD . 2 C37 C 0.4597(18) 0.9734(12) 0.0265(13) 0.053(12) Uiso 0.131(5) 1 d PRD . 2 H12 H 0.8711 0.2915 0.4846 0.037 Uiso 1 1 calc R . . H13 H 1.0679 0.2051 0.5432 0.041 Uiso 1 1 calc R . . H15 H 0.7548 -0.0023 0.7279 0.034 Uiso 1 1 calc R . . H16 H 0.5642 0.0942 0.6771 0.032 Uiso 1 1 calc R . . H22A H 1.1092 -0.0752 0.7605 0.043 Uiso 1 1 calc R . . H22B H 0.9156 -0.1166 0.7170 0.043 Uiso 1 1 calc R . . H22C H 0.9866 0.0108 0.8304 0.043 Uiso 1 1 calc R . . H23A H 1.2709 0.0508 0.6928 0.058 Uiso 1 1 calc R . . H23B H 1.2322 0.1966 0.6878 0.058 Uiso 1 1 calc R . . H23C H 1.2103 0.0766 0.5664 0.058 Uiso 1 1 calc R . . H25 H 0.1464 0.4004 0.4570 0.029 Uiso 1 1 calc R . . H26 H -0.0122 0.4044 0.3049 0.029 Uiso 1 1 calc R . . H28 H 0.3031 0.2781 0.0833 0.031 Uiso 1 1 calc R . . H29 H 0.4614 0.2766 0.2370 0.029 Uiso 1 1 calc R . . H31A H -0.0242 0.2776 -0.0765 0.042 Uiso 1 1 calc R . . H31B H 0.1026 0.1999 -0.0304 0.042 Uiso 1 1 calc R . . H31C H 0.1664 0.3591 -0.0395 0.042 Uiso 1 1 calc R . . H32A H -0.1591 0.3700 0.0321 0.040 Uiso 1 1 calc R . . H32B H -0.0769 0.4703 0.1587 0.040 Uiso 1 1 calc R . . H32C H -0.1810 0.3144 0.1549 0.040 Uiso 1 1 calc R . . H33 H 0.5559 0.9506 -0.1234 0.214 Uiso 0.369(5) 1 calc PR . 1 H37 H 0.5030 1.0504 0.0967 0.064 Uiso 0.131(5) 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 Cl34 0.076(4) 0.156(7) 0.051(4) -0.003(4) 0.001(3) 0.064(5) Cl35 0.082(3) 0.050(3) 0.064(3) 0.000(2) 0.016(2) 0.028(2) Cl36 0.201(15) 0.214(13) 0.046(4) 0.004(5) 0.016(5) -0.170(13) N17 0.038(2) 0.043(2) 0.032(2) 0.0064(18) -0.0071(18) 0.0144(19) N18 0.033(2) 0.063(3) 0.031(2) 0.013(2) 0.0029(18) 0.018(2) N19 0.038(2) 0.036(2) 0.032(2) 0.0060(17) -0.0019(17) 0.0179(18) N20 0.032(2) 0.035(2) 0.028(2) 0.0073(16) -0.0002(16) 0.0122(17) N21 0.0208(18) 0.039(2) 0.071(3) 0.032(2) -0.0009(19) 0.0076(17) N30 0.0254(18) 0.033(2) 0.0225(18) 0.0063(15) -0.0025(14) 0.0106(16) C1 0.0198(18) 0.024(2) 0.027(2) 0.0111(17) 0.0005(16) 0.0030(16) C2 0.0207(18) 0.022(2) 0.026(2) 0.0085(16) -0.0009(16) 0.0034(16) C3 0.0216(19) 0.024(2) 0.026(2) 0.0073(16) -0.0008(16) 0.0057(16) C4 0.0209(19) 0.022(2) 0.026(2) 0.0078(16) 0.0005(16) 0.0040(16) C5 0.0210(18) 0.023(2) 0.025(2) 0.0088(16) 0.0003(16) 0.0058(16) C6 0.0229(19) 0.026(2) 0.028(2) 0.0101(17) -0.0008(17) 0.0053(17) C7 0.029(2) 0.028(2) 0.027(2) 0.0083(18) -0.0015(18) 0.0063(18) C8 0.026(2) 0.039(3) 0.024(2) 0.0113(19) -0.0019(17) 0.0059(19) C9 0.024(2) 0.027(2) 0.028(2) 0.0088(18) -0.0027(17) 0.0080(17) C10 0.0235(19) 0.026(2) 0.022(2) 0.0071(16) -0.0014(16) 0.0060(17) C11 0.0212(19) 0.025(2) 0.028(2) 0.0087(17) -0.0022(16) 0.0061(16) C12 0.024(2) 0.036(2) 0.039(3) 0.020(2) 0.0013(19) 0.0083(19) C13 0.022(2) 0.037(3) 0.050(3) 0.022(2) 0.004(2) 0.0097(19) C14 0.022(2) 0.026(2) 0.044(3) 0.014(2) -0.0037(19) 0.0050(17) C15 0.025(2) 0.027(2) 0.037(2) 0.0144(19) -0.0001(18) 0.0075(18) C16 0.023(2) 0.028(2) 0.032(2) 0.0114(18) -0.0009(17) 0.0067(17) C22 0.034(2) 0.030(2) 0.049(3) 0.019(2) -0.003(2) 0.011(2) C23 0.022(2) 0.046(3) 0.088(4) 0.039(3) 0.001(3) 0.008(2) C24 0.0222(19) 0.0204(19) 0.024(2) 0.0065(16) -0.0006(16) 0.0056(16) C25 0.024(2) 0.025(2) 0.025(2) 0.0058(17) 0.0001(17) 0.0080(17) C26 0.0232(19) 0.025(2) 0.027(2) 0.0067(17) -0.0018(16) 0.0087(17) C27 0.024(2) 0.021(2) 0.025(2) 0.0085(16) -0.0014(17) 0.0063(16) C28 0.027(2) 0.029(2) 0.023(2) 0.0066(17) 0.0005(17) 0.0123(18) C29 0.025(2) 0.025(2) 0.025(2) 0.0064(17) 0.0000(17) 0.0093(17) C31 0.038(2) 0.049(3) 0.021(2) 0.006(2) -0.0012(18) 0.021(2) C32 0.029(2) 0.049(3) 0.028(2) 0.009(2) -0.0035(18) 0.019(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 Cl34 Cl36 0.512(12) 2_675 ? Cl34 C33 1.751(15) . ? Cl34 C33 1.857(16) 2_675 ? Cl35 C33 1.697(17) . ? Cl36 Cl34 0.512(12) 2_675 ? Cl36 C33 1.546(17) . ? Cl36 C33 1.797(16) 2_675 ? N17 C7 1.151(6) . ? N18 C8 1.151(6) . ? N19 C9 1.152(6) . ? N20 C10 1.155(6) . ? N21 C14 1.369(5) . ? N21 C22 1.448(6) . ? N21 C23 1.455(6) . ? N30 C27 1.339(5) . ? N30 C31 1.465(6) . ? N30 C32 1.468(5) . ? C1 C6 1.378(6) . ? C1 C5 1.434(5) . ? C1 C2 1.480(6) . ? C2 C3 1.368(6) . ? C2 C11 1.463(6) . ? C3 C9 1.428(6) . ? C3 C4 1.478(6) . ? C4 C5 1.408(6) . ? C4 C24 1.423(6) . ? C5 C10 1.420(6) . ? C6 C8 1.435(6) . ? C6 C7 1.435(6) . ? C11 C16 1.398(6) . ? C11 C12 1.405(6) . ? C12 C13 1.378(6) . ? C13 C14 1.418(6) . ? C14 C15 1.409(6) . ? C15 C16 1.376(6) . ? C24 C29 1.425(6) . ? C24 C25 1.431(5) . ? C25 C26 1.362(6) . ? C26 C27 1.424(6) . ? C27 C28 1.436(6) . ? C28 C29 1.365(6) . ? Cl38 Cl39 0.99(2) 2_675 ? Cl38 C37 1.0315 . ? Cl38 C37 2.07(3) 2_675 ? Cl38 Cl40 2.3220 . ? Cl39 Cl38 0.99(2) 2_675 ? Cl39 C37 1.16(3) 2_675 ? Cl39 C37 1.6669 . ? Cl39 Cl40 1.9425 . ? Cl40 C37 1.8491 . ? C12 H12 1.0500 . ? C13 H13 1.0500 . ? C15 H15 1.0500 . ? C16 H16 1.0500 . ? C22 H22A 1.0800 . ? C22 H22B 1.0800 . ? C22 H22C 1.0800 . ? C23 H23A 1.0800 . ? C23 H23B 1.0800 . ? C23 H23C 1.0800 . ? C25 H25 1.0500 . ? C26 H26 1.0500 . ? C28 H28 1.0500 . ? C29 H29 1.0500 . ? C31 H31A 1.0800 . ? C31 H31B 1.0800 . ? C31 H31C 1.0800 . ? C32 H32A 1.0800 . ? C32 H32B 1.0800 . ? C32 H32C 1.0800 . ? C33 H33 1.0800 . ? C37 H37 1.0800 . ? 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 Cl36 Cl34 C33 86.9(18) 2_675 . ? Cl36 Cl34 C33 46.1(16) 2_675 2_675 ? C33 Cl34 C33 44.7(10) . 2_675 ? Cl34 Cl36 C33 120.1(18) 2_675 . ? Cl34 Cl36 C33 76.6(16) 2_675 2_675 ? C33 Cl36 C33 47.9(11) . 2_675 ? C14 N21 C22 120.3(4) . . ? C14 N21 C23 120.6(4) . . ? C22 N21 C23 118.3(4) . . ? C27 N30 C31 121.6(4) . . ? C27 N30 C32 120.2(4) . . ? C31 N30 C32 118.0(3) . . ? C6 C1 C5 128.8(4) . . ? C6 C1 C2 124.5(4) . . ? C5 C1 C2 106.6(4) . . ? C3 C2 C11 127.3(4) . . ? C3 C2 C1 107.1(3) . . ? C11 C2 C1 125.5(4) . . ? C2 C3 C9 121.2(4) . . ? C2 C3 C4 110.8(4) . . ? C9 C3 C4 127.7(4) . . ? C5 C4 C24 128.9(4) . . ? C5 C4 C3 105.3(3) . . ? C24 C4 C3 125.8(4) . . ? C4 C5 C10 125.6(4) . . ? C4 C5 C1 110.1(4) . . ? C10 C5 C1 123.6(4) . . ? C1 C6 C8 122.8(4) . . ? C1 C6 C7 124.2(4) . . ? C8 C6 C7 112.9(4) . . ? N17 C7 C6 174.2(5) . . ? N18 C8 C6 176.8(5) . . ? N19 C9 C3 177.6(4) . . ? N20 C10 C5 177.7(4) . . ? C16 C11 C12 117.6(4) . . ? C16 C11 C2 121.3(4) . . ? C12 C11 C2 121.0(4) . . ? C13 C12 C11 121.2(4) . . ? C12 C13 C14 121.1(4) . . ? N21 C14 C15 122.0(4) . . ? N21 C14 C13 121.0(4) . . ? C15 C14 C13 117.1(4) . . ? C16 C15 C14 121.2(4) . . ? C15 C16 C11 121.6(4) . . ? C4 C24 C29 122.3(4) . . ? C4 C24 C25 121.7(4) . . ? C29 C24 C25 116.0(4) . . ? C26 C25 C24 122.8(4) . . ? C25 C26 C27 120.5(4) . . ? N30 C27 C26 121.4(4) . . ? N30 C27 C28 121.2(4) . . ? C26 C27 C28 117.4(4) . . ? C29 C28 C27 121.1(4) . . ? C28 C29 C24 122.0(4) . . ? Cl36 C33 Cl35 101.5(8) . . ? Cl36 C33 Cl34 146.6(12) . . ? Cl35 C33 Cl34 102.7(8) . . ? Cl39 Cl38 C37 70.0(19) 2_675 . ? Cl39 Cl38 C37 52.9(15) 2_675 2_675 ? C37 Cl38 C37 18.7(8) . 2_675 ? Cl39 Cl38 Cl40 120.0(19) 2_675 . ? C37 Cl38 Cl40 50.7 . . ? C37 Cl38 Cl40 68.9(8) 2_675 . ? Cl38 Cl39 C37 56.5(14) 2_675 2_675 ? Cl38 Cl39 C37 98.7(19) 2_675 . ? C37 Cl39 C37 43.0(14) 2_675 . ? Cl38 Cl39 Cl40 155.5(19) 2_675 . ? C37 Cl39 Cl40 104.0(14) 2_675 . ? C37 Cl39 Cl40 61.1 . . ? C37 Cl40 Cl39 52.1 . . ? C37 Cl40 Cl38 25.6 . . ? Cl39 Cl40 Cl38 77.3 . . ? Cl38 C37 Cl39 165.9 . . ? Cl38 C37 Cl40 103.8 . . ? Cl39 C37 Cl40 66.8 . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 H16 119.2 . . ? C11 C16 H16 119.2 . . ? N21 C22 H22A 109.5 . . ? N21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N21 C23 H23A 109.5 . . ? N21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C26 C25 H25 118.6 . . ? C24 C25 H25 118.6 . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 H29 119.0 . . ? C24 C29 H29 119.0 . . ? N30 C31 H31A 109.5 . . ? N30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N30 C32 H32A 109.5 . . ? N30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? Cl36 C33 H33 99.2 . . ? Cl35 C33 H33 99.2 . . ? Cl34 C33 H33 99.2 . . ? Cl38 C37 H37 95.7 . . ? Cl39 C37 H37 95.7 . . ? Cl40 C37 H37 95.7 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.038 _refine_diff_density_min -1.126 _refine_diff_density_rms 0.066 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_7 _database_code_depnum_ccdc_archive 'CCDC 801745' #TrackingRef '- JJdeposit.cif' _chemical_compound_source 'LOC ETH Zurich' _exptl_crystal_description needle _exptl_crystal_size_max .24 _exptl_crystal_size_mid .075 _exptl_crystal_size_min .009 _exptl_crystal_F_000 874 _exptl_crystal_colour 'dark red' _diffrn_ambient_temperature 100 _cell_measurement_temperature 100 _refine_ls_hydrogen_treatment constr # Submission details _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.04421 _diffrn_orient_matrix_UB_12 0.09140 _diffrn_orient_matrix_UB_13 0.03710 _diffrn_orient_matrix_UB_21 -0.04176 _diffrn_orient_matrix_UB_22 0.06452 _diffrn_orient_matrix_UB_23 -0.02992 _diffrn_orient_matrix_UB_31 -0.03479 _diffrn_orient_matrix_UB_32 0.00263 _diffrn_orient_matrix_UB_33 0.04340 _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 832.436 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z _symmetry_space_group_name_H-M 'P -1 ' _symmetry_cell_setting Triclinic _chemical_formula_moiety '2(C25 H21 N5 ), 0.5( C2 H4 Cl2) ' _chemical_formula_sum 'C51 H44 Cl N10 ' _chemical_name_systematic ; ? ; _cell_length_a 9.8044(6) _cell_length_b 12.8651(10) _cell_length_c 18.011(2) _cell_angle_alpha 93.245(5) _cell_angle_beta 91.748(5) _cell_angle_gamma 109.113(3) _cell_volume 2140.3(3) _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_number 11481 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_full 25.04 _cell_measurement_reflns_used 168410 _cell_measurement_theta_min 2.753 _cell_measurement_theta_max 25.028 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' Cl Cl 0.1484 0.1585 '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' _exptl_absorpt_coefficient_mu 0.139 _reflns_number_total 7214 _reflns_number_gt 5920 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7214 _refine_ls_number_parameters 570 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.2206 _refine_ls_wR_factor_gt 0.2097 _refine_ls_goodness_of_fit_ref 1.532 _refine_ls_restrained_S_all 1.532 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.002 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 N10 N 0.1857(3) 0.5121(2) 0.03962(15) 0.0420(7) Uani 1 1 d . . . N11 N 0.2219(3) 0.3586(2) 0.21615(15) 0.0432(7) Uani 1 1 d . . . N12 N 0.0286(3) 0.9088(2) 0.26622(13) 0.0417(7) Uani 1 1 d . . . N21 N 0.0832(3) 0.9428(2) -0.07222(13) 0.0333(6) Uani 1 1 d . . . N30 N 0.1711(3) 0.8534(2) 0.61743(13) 0.0401(6) Uani 1 1 d . . . N40 N 0.8071(4) 0.4819(3) 0.36775(17) 0.0546(8) Uani 1 1 d . . . N41 N 0.8374(3) 0.3693(2) 0.17192(16) 0.0480(7) Uani 1 1 d . . . N42 N 0.5314(3) 0.8675(2) 0.22891(14) 0.0424(7) Uani 1 1 d . . . N51 N 0.6668(3) 0.8483(2) 0.56408(14) 0.0393(6) Uani 1 1 d . . . N60 N 0.4852(3) 0.8271(2) -0.13148(13) 0.0380(6) Uani 1 1 d . . . C1 C 0.1350(3) 0.7036(2) 0.17773(15) 0.0277(6) Uani 1 1 d . . . C2 C 0.1586(3) 0.6023(2) 0.16835(15) 0.0289(6) Uani 1 1 d . . . C3 C 0.1752(3) 0.5448(2) 0.23057(16) 0.0315(6) Uani 1 1 d . . . C4 C 0.1732(3) 0.5897(2) 0.30213(15) 0.0304(6) Uani 1 1 d . . . C5 C 0.1502(3) 0.6912(2) 0.31537(15) 0.0276(6) Uani 1 1 d . . . C6 C 0.1259(3) 0.7442(2) 0.25175(15) 0.0278(6) Uani 1 1 d . . . C7 C 0.1720(3) 0.5537(3) 0.09614(17) 0.0351(7) Uani 1 1 d . . . C8 C 0.2000(3) 0.4410(3) 0.22102(16) 0.0343(7) Uani 1 1 d . . . C9 C 0.0756(3) 0.8370(3) 0.26033(15) 0.0310(7) Uani 1 1 d . . . C13 C 0.1216(3) 0.7666(2) 0.11319(14) 0.0271(6) Uani 1 1 d . . . C14 C 0.1999(3) 0.8793(2) 0.11207(15) 0.0290(6) Uani 1 1 d . . . C15 C 0.1903(3) 0.9373(2) 0.05115(15) 0.0295(6) Uani 1 1 d . . . C16 C 0.0985(3) 0.8861(2) -0.01206(15) 0.0282(6) Uani 1 1 d . . . C17 C 0.0226(3) 0.7719(2) -0.01103(15) 0.0297(6) Uani 1 1 d . . . C18 C 0.0341(3) 0.7145(2) 0.05010(15) 0.0301(6) Uani 1 1 d . . . C19 C 0.1702(3) 1.0586(3) -0.07615(16) 0.0335(7) Uani 1 1 d . . . C20 C -0.0042(3) 0.8847(3) -0.13781(15) 0.0346(7) Uani 1 1 d . . . C22 C 0.1537(3) 0.7357(2) 0.39277(15) 0.0297(6) Uani 1 1 d . . . C23 C 0.1090(3) 0.6641(3) 0.44986(15) 0.0333(7) Uani 1 1 d . . . C24 C 0.1144(3) 0.7018(3) 0.52337(16) 0.0340(7) Uani 1 1 d . . . C25 C 0.1653(3) 0.8152(3) 0.54454(15) 0.0325(7) Uani 1 1 d . . . C26 C 0.2116(3) 0.8877(3) 0.48744(15) 0.0328(7) Uani 1 1 d . . . C27 C 0.2055(3) 0.8476(3) 0.41387(15) 0.0311(6) Uani 1 1 d . . . C28 C 0.1353(4) 0.7761(3) 0.67593(17) 0.0457(8) Uani 1 1 d . . . C29 C 0.2176(4) 0.9710(3) 0.63857(17) 0.0463(8) Uani 1 1 d . . . C31 C 0.6638(3) 0.6590(2) 0.27028(16) 0.0308(6) Uani 1 1 d . . . C32 C 0.7190(3) 0.5714(3) 0.25955(17) 0.0360(7) Uani 1 1 d . . . C33 C 0.7215(3) 0.5235(3) 0.18697(17) 0.0364(7) Uani 1 1 d . . . C34 C 0.6682(3) 0.5593(3) 0.12577(17) 0.0349(7) Uani 1 1 d . . . C35 C 0.6131(3) 0.6480(3) 0.13254(16) 0.0310(6) Uani 1 1 d . . . C36 C 0.6125(3) 0.6958(3) 0.20510(16) 0.0321(7) Uani 1 1 d . . . C37 C 0.7672(4) 0.5237(3) 0.32102(18) 0.0415(8) Uani 1 1 d . . . C38 C 0.7832(4) 0.4359(3) 0.17779(18) 0.0404(7) Uani 1 1 d . . . C39 C 0.5675(3) 0.7916(3) 0.21761(15) 0.0332(7) Uani 1 1 d . . . C43 C 0.6638(3) 0.7104(2) 0.34528(16) 0.0314(6) Uani 1 1 d . . . C44 C 0.7894(3) 0.7439(3) 0.39242(16) 0.0338(7) Uani 1 1 d . . . C45 C 0.7908(3) 0.7889(3) 0.46417(17) 0.0367(7) Uani 1 1 d . . . C46 C 0.6660(3) 0.8026(3) 0.49337(16) 0.0348(7) Uani 1 1 d . . . C47 C 0.5393(3) 0.7696(3) 0.44534(16) 0.0330(7) Uani 1 1 d . . . C48 C 0.5401(3) 0.7255(3) 0.37394(16) 0.0341(7) Uani 1 1 d . . . C49 C 0.5347(4) 0.8558(3) 0.59366(18) 0.0496(9) Uani 1 1 d . . . C50 C 0.7908(4) 0.8651(3) 0.61529(19) 0.0484(9) Uani 1 1 d . . . C52 C 0.5684(3) 0.6881(2) 0.06395(16) 0.0306(6) Uani 1 1 d . . . C53 C 0.4682(3) 0.7441(3) 0.06042(15) 0.0306(6) Uani 1 1 d . . . C54 C 0.4370(3) 0.7872(3) -0.00347(15) 0.0317(7) Uani 1 1 d . . . C55 C 0.5078(3) 0.7771(3) -0.06981(15) 0.0318(7) Uani 1 1 d . . . C56 C 0.6018(3) 0.7144(3) -0.06838(16) 0.0336(7) Uani 1 1 d . . . C57 C 0.6307(3) 0.6725(3) -0.00337(16) 0.0341(7) Uani 1 1 d . . . C58 C 0.3944(4) 0.8957(3) -0.13013(18) 0.0428(8) Uani 1 1 d . . . C59 C 0.5440(4) 0.8070(4) -0.20148(17) 0.0490(9) Uani 1 1 d . . . Cl62 Cl 0.39385(14) 0.43475(9) 0.39352(6) 0.0744(4) Uani 1 1 d . . . C61 C 0.4293(6) 0.4921(5) 0.5010(4) 0.107(2) Uani 1 1 d . . . H4 H 0.1894 0.5464 0.3481 0.036 Uiso 1 1 calc R . . H14 H 0.2678 0.9207 0.1590 0.035 Uiso 1 1 calc R . . H15 H 0.2529 1.0219 0.0517 0.035 Uiso 1 1 calc R . . H17 H -0.0443 0.7296 -0.0580 0.036 Uiso 1 1 calc R . . H18 H -0.0247 0.6291 0.0491 0.036 Uiso 1 1 calc R . . H19A H 0.1684 1.1036 -0.0239 0.040 Uiso 1 1 calc R . . H19B H 0.1264 1.0931 -0.1206 0.040 Uiso 1 1 calc R . . H19C H 0.2803 1.0646 -0.0869 0.040 Uiso 1 1 calc R . . H20A H 0.0403 0.8241 -0.1609 0.041 Uiso 1 1 calc R . . H20B H -0.0042 0.9428 -0.1788 0.041 Uiso 1 1 calc R . . H20C H -0.1136 0.8439 -0.1226 0.041 Uiso 1 1 calc R . . H23 H 0.0697 0.5779 0.4359 0.040 Uiso 1 1 calc R . . H24 H 0.0796 0.6444 0.5645 0.041 Uiso 1 1 calc R . . H26 H 0.2515 0.9740 0.5010 0.039 Uiso 1 1 calc R . . H27 H 0.2417 0.9044 0.3724 0.037 Uiso 1 1 calc R . . H28A H 0.0233 0.7248 0.6682 0.055 Uiso 1 1 calc R . . H28B H 0.1529 0.8214 0.7297 0.055 Uiso 1 1 calc R . . H28C H 0.2032 0.7248 0.6732 0.055 Uiso 1 1 calc R . . H29A H 0.3301 1.0079 0.6271 0.056 Uiso 1 1 calc R . . H29B H 0.2040 0.9837 0.6973 0.056 Uiso 1 1 calc R . . H29C H 0.1533 1.0087 0.6070 0.056 Uiso 1 1 calc R . . H34 H 0.6682 0.5198 0.0725 0.042 Uiso 1 1 calc R . . H44 H 0.8856 0.7344 0.3726 0.041 Uiso 1 1 calc R . . H45 H 0.8881 0.8137 0.4978 0.044 Uiso 1 1 calc R . . H47 H 0.461(4) 0.774(3) 0.4629(18) 0.040 Uiso 1 1 d . . . H48 H 0.4438 0.7023 0.3395 0.041 Uiso 1 1 calc R . . H49A H 0.4858 0.8974 0.5559 0.060 Uiso 1 1 calc R . . H49B H 0.5587 0.9016 0.6473 0.060 Uiso 1 1 calc R . . H49C H 0.4608 0.7738 0.5999 0.060 Uiso 1 1 calc R . . H50A H 0.8106 0.7879 0.6199 0.058 Uiso 1 1 calc R . . H50B H 0.7691 0.8950 0.6694 0.058 Uiso 1 1 calc R . . H50C H 0.8847 0.9248 0.5946 0.058 Uiso 1 1 calc R . . H53 H 0.4141 0.7536 0.1090 0.037 Uiso 1 1 calc R . . H54 H 0.3594 0.8284 -0.0032 0.038 Uiso 1 1 calc R . . H56 H 0.6505 0.6995 -0.1178 0.040 Uiso 1 1 calc R . . H57 H 0.7029 0.6266 -0.0040 0.041 Uiso 1 1 calc R . . H58A H 0.2832 0.8450 -0.1254 0.051 Uiso 1 1 calc R . . H58B H 0.4041 0.9378 -0.1809 0.051 Uiso 1 1 calc R . . H58C H 0.4278 0.9557 -0.0830 0.051 Uiso 1 1 calc R . . H59A H 0.6600 0.8452 -0.1975 0.059 Uiso 1 1 calc R . . H59B H 0.4986 0.8414 -0.2454 0.059 Uiso 1 1 calc R . . H59C H 0.5171 0.7192 -0.2138 0.059 Uiso 1 1 calc R . . H61A H 0.4053 0.5676 0.5119 0.128 Uiso 1 1 calc R . . H61B H 0.3751 0.4315 0.5389 0.128 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 N10 0.0474(16) 0.0397(16) 0.0408(16) -0.0033(13) -0.0018(12) 0.0183(13) N11 0.0551(17) 0.0381(17) 0.0401(15) -0.0022(12) 0.0010(12) 0.0211(14) N12 0.0575(17) 0.0528(18) 0.0267(13) 0.0086(12) 0.0068(12) 0.0329(15) N21 0.0362(13) 0.0352(14) 0.0295(12) 0.0038(11) -0.0022(10) 0.0132(11) N30 0.0612(17) 0.0384(15) 0.0271(13) 0.0026(11) 0.0062(12) 0.0247(14) N40 0.075(2) 0.0441(18) 0.0495(17) 0.0021(14) -0.0147(15) 0.0283(17) N41 0.0561(18) 0.0398(17) 0.0546(17) 0.0031(13) -0.0050(14) 0.0256(15) N42 0.0539(17) 0.0483(18) 0.0318(14) 0.0062(12) -0.0035(12) 0.0262(14) N51 0.0411(14) 0.0433(16) 0.0327(14) 0.0062(12) -0.0046(11) 0.0128(13) N60 0.0423(15) 0.0500(17) 0.0288(13) 0.0080(12) 0.0031(11) 0.0239(13) C1 0.0246(13) 0.0286(15) 0.0294(14) -0.0003(12) -0.0019(11) 0.0088(12) C2 0.0298(14) 0.0283(15) 0.0288(14) -0.0010(12) -0.0008(11) 0.0105(12) C3 0.0321(15) 0.0285(16) 0.0336(16) 0.0004(12) -0.0010(12) 0.0102(13) C4 0.0318(15) 0.0308(16) 0.0306(15) 0.0023(12) -0.0014(12) 0.0135(13) C5 0.0250(14) 0.0311(16) 0.0284(14) 0.0018(12) 0.0024(11) 0.0117(12) C6 0.0293(14) 0.0275(15) 0.0282(14) 0.0022(12) 0.0001(11) 0.0115(12) C7 0.0376(16) 0.0303(17) 0.0385(17) -0.0005(14) -0.0015(13) 0.0134(14) C8 0.0398(17) 0.0307(18) 0.0334(16) -0.0011(13) -0.0006(13) 0.0137(14) C9 0.0362(15) 0.0378(18) 0.0214(14) 0.0032(12) 0.0022(11) 0.0154(14) C13 0.0261(14) 0.0311(16) 0.0242(14) 0.0003(11) 0.0012(11) 0.0099(12) C14 0.0302(14) 0.0336(16) 0.0250(14) -0.0034(12) 0.0005(11) 0.0137(13) C15 0.0310(15) 0.0296(16) 0.0284(14) -0.0012(12) 0.0038(11) 0.0109(12) C16 0.0272(14) 0.0333(16) 0.0280(14) 0.0012(12) 0.0029(11) 0.0152(13) C17 0.0318(15) 0.0332(17) 0.0267(14) -0.0004(12) 0.0012(11) 0.0146(13) C18 0.0321(15) 0.0290(16) 0.0306(15) 0.0011(12) 0.0014(12) 0.0123(13) C19 0.0355(16) 0.0318(17) 0.0342(16) 0.0058(13) 0.0053(12) 0.0117(13) C20 0.0438(17) 0.0375(18) 0.0250(14) -0.0002(12) -0.0053(12) 0.0180(14) C22 0.0292(14) 0.0336(17) 0.0291(14) 0.0037(12) -0.0012(11) 0.0141(13) C23 0.0422(17) 0.0326(17) 0.0290(15) 0.0021(12) -0.0011(12) 0.0177(14) C24 0.0434(17) 0.0356(17) 0.0274(15) 0.0051(13) 0.0032(12) 0.0183(14) C25 0.0389(16) 0.0374(18) 0.0265(15) 0.0019(13) 0.0010(12) 0.0198(14) C26 0.0408(16) 0.0304(16) 0.0302(15) 0.0020(12) -0.0002(12) 0.0163(13) C27 0.0347(15) 0.0325(16) 0.0294(15) 0.0044(12) 0.0006(12) 0.0154(13) C28 0.071(2) 0.045(2) 0.0266(16) 0.0052(14) 0.0084(15) 0.0257(18) C29 0.068(2) 0.042(2) 0.0312(16) -0.0004(14) 0.0057(15) 0.0219(18) C31 0.0287(14) 0.0303(16) 0.0331(15) 0.0072(12) 0.0005(12) 0.0087(12) C32 0.0354(16) 0.0348(17) 0.0393(17) 0.0113(13) -0.0018(13) 0.0124(13) C33 0.0330(15) 0.0332(17) 0.0445(18) 0.0061(14) 0.0022(13) 0.0121(13) C34 0.0327(15) 0.0359(17) 0.0378(16) 0.0094(13) 0.0022(12) 0.0126(13) C35 0.0243(14) 0.0333(16) 0.0344(16) 0.0085(13) 0.0050(11) 0.0068(12) C36 0.0270(14) 0.0360(17) 0.0349(16) 0.0105(13) 0.0026(12) 0.0113(13) C37 0.0468(18) 0.0358(18) 0.0438(18) 0.0030(15) -0.0070(14) 0.0172(15) C38 0.0421(18) 0.0378(19) 0.0429(18) 0.0069(14) -0.0009(14) 0.0151(15) C39 0.0362(16) 0.0393(18) 0.0259(15) 0.0075(13) 0.0012(12) 0.0140(14) C43 0.0321(15) 0.0304(16) 0.0322(15) 0.0106(12) 0.0012(12) 0.0098(13) C44 0.0306(15) 0.0312(17) 0.0406(17) 0.0083(13) -0.0014(12) 0.0110(13) C45 0.0312(15) 0.0329(17) 0.0453(18) 0.0100(14) -0.0066(13) 0.0094(13) C46 0.0387(17) 0.0315(17) 0.0328(16) 0.0077(13) -0.0048(13) 0.0093(14) C47 0.0278(15) 0.0388(18) 0.0323(16) 0.0093(13) 0.0031(12) 0.0094(13) C48 0.0301(15) 0.0378(18) 0.0342(16) 0.0106(13) -0.0023(12) 0.0099(13) C49 0.052(2) 0.063(2) 0.0307(17) 0.0052(16) 0.0050(15) 0.0146(18) C50 0.050(2) 0.048(2) 0.0424(19) -0.0012(16) -0.0184(15) 0.0125(17) C52 0.0268(14) 0.0314(16) 0.0330(15) 0.0065(12) 0.0024(12) 0.0079(12) C53 0.0279(14) 0.0380(17) 0.0270(14) 0.0038(12) 0.0010(11) 0.0123(13) C54 0.0315(15) 0.0382(17) 0.0288(15) 0.0003(12) -0.0005(12) 0.0165(13) C55 0.0309(15) 0.0374(17) 0.0273(15) 0.0049(12) -0.0005(11) 0.0112(13) C56 0.0322(15) 0.0390(18) 0.0312(15) 0.0041(13) 0.0030(12) 0.0135(13) C57 0.0322(15) 0.0341(17) 0.0383(16) 0.0047(13) 0.0039(13) 0.0135(13) C58 0.0486(19) 0.052(2) 0.0361(17) 0.0117(15) -0.0008(14) 0.0274(17) C59 0.055(2) 0.072(3) 0.0307(16) 0.0151(16) 0.0092(15) 0.0332(19) Cl62 0.1145(9) 0.0454(6) 0.0517(6) 0.0092(4) -0.0283(6) 0.0127(6) C61 0.090(4) 0.069(3) 0.179(6) 0.060(4) 0.061(4) 0.037(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 N10 C7 1.155(4) . ? N11 C8 1.149(4) . ? N12 C9 1.161(4) . ? N21 C16 1.371(4) . ? N21 C20 1.451(4) . ? N21 C19 1.461(4) . ? N30 C25 1.368(4) . ? N30 C29 1.454(4) . ? N30 C28 1.462(4) . ? N40 C37 1.150(4) . ? N41 C38 1.149(4) . ? N42 C39 1.153(4) . ? N51 C46 1.371(4) . ? N51 C49 1.445(4) . ? N51 C50 1.454(4) . ? N60 C55 1.362(4) . ? N60 C58 1.445(4) . ? N60 C59 1.447(4) . ? C1 C2 1.399(4) . ? C1 C6 1.420(4) . ? C1 C13 1.481(4) . ? C2 C3 1.410(4) . ? C2 C7 1.439(4) . ? C3 C4 1.386(4) . ? C3 C8 1.436(4) . ? C4 C5 1.404(4) . ? C5 C6 1.419(4) . ? C5 C22 1.472(4) . ? C6 C9 1.436(4) . ? C13 C18 1.398(4) . ? C13 C14 1.402(4) . ? C14 C15 1.379(4) . ? C15 C16 1.415(4) . ? C16 C17 1.414(4) . ? C17 C18 1.382(4) . ? C22 C27 1.387(4) . ? C22 C23 1.402(4) . ? C23 C24 1.377(4) . ? C24 C25 1.404(4) . ? C25 C26 1.412(4) . ? C26 C27 1.387(4) . ? C31 C32 1.407(4) . ? C31 C36 1.428(4) . ? C31 C43 1.470(4) . ? C32 C33 1.418(4) . ? C32 C37 1.435(4) . ? C33 C34 1.371(4) . ? C33 C38 1.448(4) . ? C34 C35 1.414(4) . ? C35 C36 1.414(4) . ? C35 C52 1.474(4) . ? C36 C39 1.447(4) . ? C43 C48 1.398(4) . ? C43 C44 1.404(4) . ? C44 C45 1.384(4) . ? C45 C46 1.405(4) . ? C46 C47 1.421(4) . ? C47 C48 1.377(4) . ? C52 C53 1.397(4) . ? C52 C57 1.408(4) . ? C53 C54 1.374(4) . ? C54 C55 1.421(4) . ? C55 C56 1.409(4) . ? C56 C57 1.376(4) . ? Cl62 C61 2.011(8) . ? C61 C61 1.337(11) 2_666 ? C4 H4 1.0600 . ? C14 H14 1.0600 . ? C15 H15 1.0600 . ? C17 H17 1.0600 . ? C18 H18 1.0600 . ? C19 H19A 1.0800 . ? C19 H19B 1.0800 . ? C19 H19C 1.0800 . ? C20 H20A 1.0800 . ? C20 H20B 1.0800 . ? C20 H20C 1.0800 . ? C23 H23 1.0600 . ? C24 H24 1.0600 . ? C26 H26 1.0600 . ? C27 H27 1.0600 . ? C28 H28A 1.0800 . ? C28 H28B 1.0800 . ? C28 H28C 1.0800 . ? C29 H29A 1.0800 . ? C29 H29B 1.0800 . ? C29 H29C 1.0800 . ? C34 H34 1.0600 . ? C44 H44 1.0600 . ? C45 H45 1.0600 . ? C47 H47 0.86(3) . ? C48 H48 1.0600 . ? C49 H49A 1.0800 . ? C49 H49B 1.0800 . ? C49 H49C 1.0800 . ? C50 H50A 1.0800 . ? C50 H50B 1.0800 . ? C50 H50C 1.0800 . ? C53 H53 1.0600 . ? C54 H54 1.0600 . ? C56 H56 1.0600 . ? C57 H57 1.0600 . ? C58 H58A 1.0800 . ? C58 H58B 1.0800 . ? C58 H58C 1.0800 . ? C59 H59A 1.0800 . ? C59 H59B 1.0800 . ? C59 H59C 1.0800 . ? C61 H61A 1.0800 . ? C61 H61B 1.0800 . ? 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 C16 N21 C20 120.2(3) . . ? C16 N21 C19 120.8(2) . . ? C20 N21 C19 118.4(2) . . ? C25 N30 C29 121.0(3) . . ? C25 N30 C28 120.2(3) . . ? C29 N30 C28 118.7(2) . . ? C46 N51 C49 120.3(3) . . ? C46 N51 C50 119.5(3) . . ? C49 N51 C50 118.6(3) . . ? C55 N60 C58 121.0(2) . . ? C55 N60 C59 120.7(2) . . ? C58 N60 C59 118.1(2) . . ? C2 C1 C6 117.3(2) . . ? C2 C1 C13 121.4(2) . . ? C6 C1 C13 121.3(2) . . ? C1 C2 C3 120.6(2) . . ? C1 C2 C7 122.3(2) . . ? C3 C2 C7 117.0(2) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 C8 118.8(3) . . ? C2 C3 C8 120.7(2) . . ? C3 C4 C5 121.7(3) . . ? C4 C5 C6 116.6(2) . . ? C4 C5 C22 118.9(2) . . ? C6 C5 C22 124.5(2) . . ? C5 C6 C1 123.1(2) . . ? C5 C6 C9 119.8(2) . . ? C1 C6 C9 116.8(2) . . ? N10 C7 C2 177.2(3) . . ? N11 C8 C3 177.4(3) . . ? N12 C9 C6 176.8(3) . . ? C18 C13 C14 117.8(3) . . ? C18 C13 C1 120.9(3) . . ? C14 C13 C1 121.3(3) . . ? C15 C14 C13 121.3(3) . . ? C14 C15 C16 121.4(3) . . ? N21 C16 C17 120.7(3) . . ? N21 C16 C15 122.5(3) . . ? C17 C16 C15 116.8(3) . . ? C18 C17 C16 121.2(3) . . ? C17 C18 C13 121.5(3) . . ? C27 C22 C23 116.7(3) . . ? C27 C22 C5 123.0(3) . . ? C23 C22 C5 120.3(3) . . ? C24 C23 C22 122.4(3) . . ? C23 C24 C25 120.9(3) . . ? N30 C25 C24 121.3(3) . . ? N30 C25 C26 121.6(3) . . ? C24 C25 C26 117.0(3) . . ? C27 C26 C25 120.9(3) . . ? C26 C27 C22 122.1(3) . . ? C32 C31 C36 116.7(3) . . ? C32 C31 C43 120.6(2) . . ? C36 C31 C43 122.7(3) . . ? C31 C32 C33 120.4(3) . . ? C31 C32 C37 121.8(3) . . ? C33 C32 C37 117.7(3) . . ? C34 C33 C32 121.3(3) . . ? C34 C33 C38 119.8(3) . . ? C32 C33 C38 118.9(3) . . ? C33 C34 C35 121.1(3) . . ? C34 C35 C36 117.0(3) . . ? C34 C35 C52 118.3(3) . . ? C36 C35 C52 124.6(3) . . ? C35 C36 C31 123.4(3) . . ? C35 C36 C39 121.4(2) . . ? C31 C36 C39 115.1(2) . . ? N40 C37 C32 176.6(4) . . ? N41 C38 C33 177.2(4) . . ? N42 C39 C36 178.8(3) . . ? C48 C43 C44 116.9(3) . . ? C48 C43 C31 122.5(3) . . ? C44 C43 C31 120.6(3) . . ? C45 C44 C43 121.7(3) . . ? C44 C45 C46 121.4(3) . . ? N51 C46 C45 121.8(3) . . ? N51 C46 C47 121.3(3) . . ? C45 C46 C47 116.8(3) . . ? C48 C47 C46 121.0(3) . . ? C47 C48 C43 122.2(3) . . ? C53 C52 C57 116.0(3) . . ? C53 C52 C35 124.4(2) . . ? C57 C52 C35 119.6(2) . . ? C54 C53 C52 122.7(3) . . ? C53 C54 C55 120.6(3) . . ? N60 C55 C56 122.2(2) . . ? N60 C55 C54 120.6(3) . . ? C56 C55 C54 117.2(3) . . ? C57 C56 C55 120.5(3) . . ? C56 C57 C52 122.7(3) . . ? C61 C61 Cl62 92.1(6) 2_666 . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 H18 119.3 . . ? C13 C18 H18 119.3 . . ? N21 C19 H19A 109.5 . . ? N21 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N21 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N21 C20 H20A 109.5 . . ? N21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C24 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C27 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C26 C27 H27 118.9 . . ? C22 C27 H27 118.9 . . ? N30 C28 H28A 109.5 . . ? N30 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N30 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N30 C29 H29A 109.5 . . ? N30 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N30 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C33 C34 H34 119.5 . . ? C35 C34 H34 119.5 . . ? C45 C44 H44 119.2 . . ? C43 C44 H44 119.2 . . ? C44 C45 H45 119.3 . . ? C46 C45 H45 119.3 . . ? C48 C47 H47 121(2) . . ? C46 C47 H47 118(2) . . ? C47 C48 H48 118.9 . . ? C43 C48 H48 118.9 . . ? N51 C49 H49A 109.5 . . ? N51 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? N51 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? N51 C50 H50A 109.5 . . ? N51 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? N51 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C54 C53 H53 118.6 . . ? C52 C53 H53 118.6 . . ? C53 C54 H54 119.7 . . ? C55 C54 H54 119.7 . . ? C57 C56 H56 119.7 . . ? C55 C56 H56 119.7 . . ? C56 C57 H57 118.6 . . ? C52 C57 H57 118.6 . . ? N60 C58 H58A 109.5 . . ? N60 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? N60 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? N60 C59 H59A 109.5 . . ? N60 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? N60 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C61 C61 H61A 113.3 2_666 . ? Cl62 C61 H61A 113.3 . . ? C61 C61 H61B 113.3 2_666 . ? Cl62 C61 H61B 113.3 . . ? H61A C61 H61B 110.6 . . ? 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 C1 C2 C3 -1.1(4) . . . . ? C13 C1 C2 C3 178.2(3) . . . . ? C6 C1 C2 C7 -179.0(3) . . . . ? C13 C1 C2 C7 0.3(4) . . . . ? C1 C2 C3 C4 -2.2(4) . . . . ? C7 C2 C3 C4 175.8(3) . . . . ? C1 C2 C3 C8 -179.7(3) . . . . ? C7 C2 C3 C8 -1.7(4) . . . . ? C2 C3 C4 C5 2.1(4) . . . . ? C8 C3 C4 C5 179.7(3) . . . . ? C3 C4 C5 C6 1.4(4) . . . . ? C3 C4 C5 C22 -178.2(3) . . . . ? C4 C5 C6 C1 -4.9(4) . . . . ? C22 C5 C6 C1 174.6(3) . . . . ? C4 C5 C6 C9 168.6(3) . . . . ? C22 C5 C6 C9 -11.9(4) . . . . ? C2 C1 C6 C5 4.8(4) . . . . ? C13 C1 C6 C5 -174.6(3) . . . . ? C2 C1 C6 C9 -168.9(3) . . . . ? C13 C1 C6 C9 11.8(4) . . . . ? C1 C2 C7 N10 159(7) . . . . ? C3 C2 C7 N10 -19(7) . . . . ? C4 C3 C8 N11 -17(8) . . . . ? C2 C3 C8 N11 161(7) . . . . ? C5 C6 C9 N12 -102(5) . . . . ? C1 C6 C9 N12 72(5) . . . . ? C2 C1 C13 C18 46.4(4) . . . . ? C6 C1 C13 C18 -134.3(3) . . . . ? C2 C1 C13 C14 -131.2(3) . . . . ? C6 C1 C13 C14 48.1(4) . . . . ? C18 C13 C14 C15 0.5(4) . . . . ? C1 C13 C14 C15 178.2(2) . . . . ? C13 C14 C15 C16 1.5(4) . . . . ? C20 N21 C16 C17 -4.0(4) . . . . ? C19 N21 C16 C17 -174.9(2) . . . . ? C20 N21 C16 C15 175.5(2) . . . . ? C19 N21 C16 C15 4.6(4) . . . . ? C14 C15 C16 N21 177.6(2) . . . . ? C14 C15 C16 C17 -2.8(4) . . . . ? N21 C16 C17 C18 -178.2(2) . . . . ? C15 C16 C17 C18 2.3(4) . . . . ? C16 C17 C18 C13 -0.3(4) . . . . ? C14 C13 C18 C17 -1.1(4) . . . . ? C1 C13 C18 C17 -178.8(2) . . . . ? C4 C5 C22 C27 145.9(3) . . . . ? C6 C5 C22 C27 -33.6(4) . . . . ? C4 C5 C22 C23 -31.4(4) . . . . ? C6 C5 C22 C23 149.0(3) . . . . ? C27 C22 C23 C24 0.6(4) . . . . ? C5 C22 C23 C24 178.0(3) . . . . ? C22 C23 C24 C25 0.2(4) . . . . ? C29 N30 C25 C24 -177.1(3) . . . . ? C28 N30 C25 C24 5.1(4) . . . . ? C29 N30 C25 C26 3.6(4) . . . . ? C28 N30 C25 C26 -174.2(3) . . . . ? C23 C24 C25 N30 -179.9(3) . . . . ? C23 C24 C25 C26 -0.6(4) . . . . ? N30 C25 C26 C27 179.7(3) . . . . ? C24 C25 C26 C27 0.4(4) . . . . ? C25 C26 C27 C22 0.3(4) . . . . ? C23 C22 C27 C26 -0.8(4) . . . . ? C5 C22 C27 C26 -178.2(3) . . . . ? C36 C31 C32 C33 -0.3(4) . . . . ? C43 C31 C32 C33 -178.7(3) . . . . ? C36 C31 C32 C37 -176.9(3) . . . . ? C43 C31 C32 C37 4.6(5) . . . . ? C31 C32 C33 C34 -1.3(5) . . . . ? C37 C32 C33 C34 175.5(3) . . . . ? C31 C32 C33 C38 178.1(3) . . . . ? C37 C32 C33 C38 -5.1(4) . . . . ? C32 C33 C34 C35 2.2(5) . . . . ? C38 C33 C34 C35 -177.1(3) . . . . ? C33 C34 C35 C36 -1.5(4) . . . . ? C33 C34 C35 C52 175.1(3) . . . . ? C34 C35 C36 C31 0.0(4) . . . . ? C52 C35 C36 C31 -176.5(3) . . . . ? C34 C35 C36 C39 175.8(3) . . . . ? C52 C35 C36 C39 -0.6(4) . . . . ? C32 C31 C36 C35 0.9(4) . . . . ? C43 C31 C36 C35 179.3(3) . . . . ? C32 C31 C36 C39 -175.2(3) . . . . ? C43 C31 C36 C39 3.2(4) . . . . ? C31 C32 C37 N40 177(6) . . . . ? C33 C32 C37 N40 0(7) . . . . ? C34 C33 C38 N41 123(7) . . . . ? C32 C33 C38 N41 -57(7) . . . . ? C35 C36 C39 N42 165(15) . . . . ? C31 C36 C39 N42 -19(15) . . . . ? C32 C31 C43 C48 -129.0(3) . . . . ? C36 C31 C43 C48 52.6(4) . . . . ? C32 C31 C43 C44 49.1(4) . . . . ? C36 C31 C43 C44 -129.3(3) . . . . ? C48 C43 C44 C45 0.5(4) . . . . ? C31 C43 C44 C45 -177.7(3) . . . . ? C43 C44 C45 C46 0.4(5) . . . . ? C49 N51 C46 C45 -176.7(3) . . . . ? C50 N51 C46 C45 -11.3(4) . . . . ? C49 N51 C46 C47 5.0(4) . . . . ? C50 N51 C46 C47 170.4(3) . . . . ? C44 C45 C46 N51 -179.3(3) . . . . ? C44 C45 C46 C47 -0.9(4) . . . . ? N51 C46 C47 C48 178.9(3) . . . . ? C45 C46 C47 C48 0.5(4) . . . . ? C46 C47 C48 C43 0.4(5) . . . . ? C44 C43 C48 C47 -0.9(4) . . . . ? C31 C43 C48 C47 177.2(3) . . . . ? C34 C35 C52 C53 156.0(3) . . . . ? C36 C35 C52 C53 -27.7(5) . . . . ? C34 C35 C52 C57 -25.4(4) . . . . ? C36 C35 C52 C57 151.0(3) . . . . ? C57 C52 C53 C54 -3.5(5) . . . . ? C35 C52 C53 C54 175.2(3) . . . . ? C52 C53 C54 C55 -0.5(5) . . . . ? C58 N60 C55 C56 -176.6(3) . . . . ? C59 N60 C55 C56 7.4(5) . . . . ? C58 N60 C55 C54 2.9(5) . . . . ? C59 N60 C55 C54 -173.0(3) . . . . ? C53 C54 C55 N60 -174.9(3) . . . . ? C53 C54 C55 C56 4.7(5) . . . . ? N60 C55 C56 C57 174.8(3) . . . . ? C54 C55 C56 C57 -4.8(5) . . . . ? C55 C56 C57 C52 0.8(5) . . . . ? C53 C52 C57 C56 3.4(5) . . . . ? C35 C52 C57 C56 -175.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.799 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.057 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; data_4 _database_code_depnum_ccdc_archive 'CCDC 801746' #TrackingRef '- JJdeposit.cif' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C27 H21 N7' _chemical_formula_sum 'C27 H21 N7' _chemical_formula_iupac ? _chemical_formula_weight 443.50 _chemical_absolute_configuration ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 '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 23.1039(7) _cell_length_b 6.0491(2) _cell_length_c 15.7821(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.218(2) _cell_angle_gamma 90.00 _cell_volume 2204.02(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2609 _cell_measurement_theta_min 3.83 _cell_measurement_theta_max 50.10 _exptl_crystal_description plate _exptl_crystal_colour red-brown _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.663 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9247 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus 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 8349 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 50.31 _reflns_number_total 2263 _reflns_number_gt 1873 _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2263 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 0.854 _refine_ls_restrained_S_all 0.854 _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 N8 N 0.26641(8) 0.4574(3) 0.31796(14) 0.0354(6) Uani 1 1 d . . . N10 N 0.26804(8) 1.0805(4) 0.45567(12) 0.0373(6) Uani 1 1 d . . . N12 N 0.39934(10) 0.6492(4) 0.49464(13) 0.0419(6) Uani 1 1 d . . . N19 N 0.45086(8) 0.2013(3) 0.84893(12) 0.0326(6) Uani 1 1 d . . . N23 N 0.19434(7) 0.5860(3) 0.77822(14) 0.0278(5) Uani 1 1 d . . . N25 N 0.20394(8) 0.0071(4) 0.63070(12) 0.0316(5) Uani 1 1 d . . . N32 N -0.06622(8) 0.5867(3) 0.64718(12) 0.0325(5) Uani 1 1 d . . . C1 C 0.24975(9) 0.6515(4) 0.46378(13) 0.0228(6) Uani 1 1 d . . . C2 C 0.29306(9) 0.5710(3) 0.53195(14) 0.0221(6) Uani 1 1 d . . . C3 C 0.27922(9) 0.4823(3) 0.60551(14) 0.0213(6) Uani 1 1 d . . . C4 C 0.21558(9) 0.4409(3) 0.62546(14) 0.0230(6) Uani 1 1 d . . . C5 C 0.17081(9) 0.5371(3) 0.56063(14) 0.0226(6) Uani 1 1 d . . . C6 C 0.18771(9) 0.6180(4) 0.48788(15) 0.0227(6) Uani 1 1 d . . . H6 H 0.1574(8) 0.682(3) 0.4452(12) 0.009(5) Uiso 1 1 d . . . C7 C 0.25986(9) 0.5429(4) 0.38150(17) 0.0245(6) Uani 1 1 d . . . C9 C 0.25972(9) 0.8940(5) 0.45495(13) 0.0248(6) Uani 1 1 d . . . C11 C 0.35282(11) 0.6096(4) 0.51328(14) 0.0293(6) Uani 1 1 d . . . C13 C 0.32420(9) 0.4092(3) 0.66940(13) 0.0202(6) Uani 1 1 d . . . C14 C 0.33654(9) 0.5321(4) 0.74180(14) 0.0249(6) Uani 1 1 d . . . H14 H 0.3171(10) 0.669(4) 0.7528(14) 0.039(7) Uiso 1 1 d . . . C15 C 0.37808(9) 0.4645(4) 0.80096(16) 0.0259(6) Uani 1 1 d . . . H15 H 0.3850(9) 0.556(4) 0.8490(14) 0.023(6) Uiso 1 1 d . . . C16 C 0.40916(9) 0.2673(4) 0.79003(14) 0.0252(6) Uani 1 1 d . . . C17 C 0.39703(10) 0.1443(4) 0.71578(14) 0.0269(6) Uani 1 1 d . . . H17 H 0.4175(10) 0.004(4) 0.7057(14) 0.034(7) Uiso 1 1 d . . . C18 C 0.35536(9) 0.2151(4) 0.65711(16) 0.0259(6) Uani 1 1 d . . . H18 H 0.3478(9) 0.131(3) 0.6069(14) 0.024(6) Uiso 1 1 d . . . C20 C 0.46247(13) 0.3308(5) 0.92488(18) 0.0364(7) Uani 1 1 d . . . H20B H 0.4777(10) 0.483(5) 0.9081(15) 0.042(7) Uiso 1 1 d . . . H20C H 0.4887(11) 0.247(4) 0.9609(16) 0.046(7) Uiso 1 1 d . . . H20A H 0.4283(12) 0.353(4) 0.9587(16) 0.053(8) Uiso 1 1 d . . . C21 C 0.48658(12) 0.0110(5) 0.8330(2) 0.0364(7) Uani 1 1 d . . . H21B H 0.4645(11) -0.130(5) 0.8293(16) 0.055(8) Uiso 1 1 d . . . H21C H 0.5134(12) 0.002(4) 0.8767(17) 0.043(8) Uiso 1 1 d . . . H21A H 0.5045(11) 0.024(4) 0.7765(18) 0.052(8) Uiso 1 1 d . . . C22 C 0.20423(9) 0.5247(4) 0.71187(16) 0.0216(6) Uani 1 1 d . . . C24 C 0.20884(9) 0.1952(5) 0.62861(14) 0.0243(6) Uani 1 1 d . . . C26 C 0.10933(9) 0.5427(4) 0.58414(14) 0.0234(6) Uani 1 1 d . . . C27 C 0.08366(10) 0.3853(4) 0.63472(15) 0.0277(6) Uani 1 1 d . . . H27 H 0.1054(9) 0.266(4) 0.6578(13) 0.025(6) Uiso 1 1 d . . . C28 C 0.02634(10) 0.3983(4) 0.65584(15) 0.0291(6) Uani 1 1 d . . . H28 H 0.0099(9) 0.286(4) 0.6917(14) 0.028(6) Uiso 1 1 d . . . C29 C -0.00901(10) 0.5731(4) 0.62671(14) 0.0273(6) Uani 1 1 d . . . C30 C 0.01663(10) 0.7337(4) 0.57667(15) 0.0308(6) Uani 1 1 d . . . H30 H -0.0048(10) 0.859(4) 0.5558(15) 0.043(7) Uiso 1 1 d . . . C31 C 0.07393(10) 0.7184(4) 0.55638(15) 0.0293(6) Uani 1 1 d . . . H31 H 0.0898(9) 0.840(4) 0.5262(13) 0.026(6) Uiso 1 1 d . . . C33 C -0.08940(12) 0.4341(5) 0.70686(19) 0.0354(7) Uani 1 1 d . . . H33A H -0.0896(9) 0.271(4) 0.6831(15) 0.045(7) Uiso 1 1 d . . . H33B H -0.1303(12) 0.470(4) 0.7151(15) 0.047(7) Uiso 1 1 d . . . H33C H -0.0670(9) 0.440(3) 0.7626(14) 0.020(6) Uiso 1 1 d . . . C34 C -0.10033(11) 0.7757(4) 0.61905(19) 0.0349(7) Uani 1 1 d . . . H34A H -0.0987(10) 0.785(4) 0.5522(17) 0.045(7) Uiso 1 1 d . . . H34B H -0.1392(11) 0.755(4) 0.6388(14) 0.038(7) Uiso 1 1 d . . . H34C H -0.0842(10) 0.921(4) 0.6443(16) 0.047(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N8 0.0409(14) 0.0306(13) 0.0343(14) 0.0025(11) -0.0019(11) 0.0059(10) N10 0.0479(15) 0.0339(16) 0.0302(13) -0.0002(10) 0.0034(10) -0.0053(11) N12 0.0278(14) 0.0541(15) 0.0437(14) 0.0068(11) 0.0003(11) -0.0038(11) N19 0.0273(11) 0.0373(13) 0.0325(12) -0.0035(10) -0.0062(10) 0.0126(10) N23 0.0211(11) 0.0277(12) 0.0346(14) -0.0012(10) 0.0005(9) 0.0010(9) N25 0.0282(12) 0.0339(15) 0.0330(13) -0.0023(10) 0.0027(9) -0.0012(10) N32 0.0195(12) 0.0360(13) 0.0423(13) 0.0034(11) 0.0046(9) 0.0019(10) C1 0.0219(13) 0.0215(15) 0.0249(14) 0.0023(11) -0.0007(10) 0.0014(10) C2 0.0195(14) 0.0223(14) 0.0246(14) -0.0008(11) 0.0010(11) -0.0016(10) C3 0.0190(13) 0.0174(13) 0.0274(15) -0.0039(11) 0.0008(11) -0.0015(10) C4 0.0203(13) 0.0226(15) 0.0263(14) 0.0008(11) 0.0011(10) -0.0014(10) C5 0.0201(13) 0.0192(13) 0.0283(15) -0.0013(11) -0.0008(11) -0.0014(10) C6 0.0179(13) 0.0223(14) 0.0277(15) 0.0010(11) -0.0022(11) -0.0010(11) C7 0.0218(14) 0.0219(14) 0.0297(16) 0.0051(13) -0.0003(11) 0.0016(10) C9 0.0230(14) 0.0297(19) 0.0217(14) 0.0011(11) 0.0008(10) -0.0019(12) C11 0.0295(18) 0.0294(16) 0.0287(15) 0.0037(11) -0.0024(12) 0.0000(12) C13 0.0166(12) 0.0193(14) 0.0248(14) -0.0004(11) 0.0027(10) -0.0020(11) C14 0.0168(13) 0.0251(15) 0.0330(15) -0.0028(12) 0.0025(12) 0.0027(11) C15 0.0204(14) 0.0312(15) 0.0260(15) -0.0057(13) 0.0003(12) 0.0006(12) C16 0.0168(12) 0.0295(15) 0.0293(15) 0.0025(12) 0.0020(11) -0.0008(12) C17 0.0217(13) 0.0260(15) 0.0329(16) -0.0004(12) -0.0004(11) 0.0028(12) C18 0.0233(14) 0.0281(15) 0.0263(15) -0.0042(13) 0.0010(12) -0.0021(12) C20 0.0330(17) 0.041(2) 0.0342(16) -0.0011(14) -0.0087(14) 0.0102(15) C21 0.0308(16) 0.039(2) 0.0394(19) -0.0021(14) -0.0058(15) 0.0080(15) C22 0.0149(13) 0.0200(14) 0.0297(17) 0.0031(12) -0.0025(11) 0.0005(10) C24 0.0188(13) 0.0295(18) 0.0245(14) -0.0008(12) -0.0010(10) -0.0012(12) C26 0.0200(13) 0.0231(14) 0.0268(14) -0.0004(11) -0.0026(11) -0.0001(11) C27 0.0237(15) 0.0276(16) 0.0314(15) 0.0048(12) -0.0036(11) 0.0013(13) C28 0.0211(15) 0.0337(16) 0.0326(15) 0.0053(13) 0.0022(11) -0.0034(13) C29 0.0186(14) 0.0319(15) 0.0314(15) -0.0041(12) 0.0009(11) -0.0028(12) C30 0.0227(15) 0.0324(16) 0.0370(15) 0.0028(14) -0.0022(12) 0.0052(13) C31 0.0268(15) 0.0290(16) 0.0323(15) 0.0034(13) 0.0019(11) -0.0023(13) C33 0.0216(16) 0.0385(19) 0.0464(19) -0.0035(15) 0.0054(14) -0.0040(13) C34 0.0197(15) 0.0327(18) 0.052(2) -0.0102(14) 0.0027(13) 0.0042(13) _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 N8 C7 1.144(3) . ? N10 C9 1.145(3) . ? N12 C11 1.150(3) . ? N19 C16 1.372(3) . ? N19 C21 1.444(3) . ? N19 C20 1.448(3) . ? N23 C22 1.142(3) . ? N25 C24 1.144(3) . ? N32 C29 1.375(3) . ? N32 C33 1.437(3) . ? N32 C34 1.448(3) . ? C1 C7 1.482(4) . ? C1 C9 1.492(4) . ? C1 C6 1.511(3) . ? C1 C2 1.521(3) . ? C2 C3 1.329(3) . ? C2 C11 1.442(3) . ? C3 C13 1.487(3) . ? C3 C4 1.536(3) . ? C4 C22 1.488(4) . ? C4 C24 1.495(4) . ? C4 C5 1.541(3) . ? C5 C6 1.321(3) . ? C5 C26 1.482(3) . ? C6 H6 1.028(19) . ? C13 C14 1.383(3) . ? C13 C18 1.395(3) . ? C14 C15 1.375(3) . ? C14 H14 0.96(2) . ? C15 C16 1.407(3) . ? C15 H15 0.95(2) . ? C16 C17 1.407(3) . ? C17 C18 1.378(3) . ? C17 H17 0.99(2) . ? C18 H18 0.95(2) . ? C20 H20B 1.03(3) . ? C20 H20C 0.96(3) . ? C20 H20A 0.98(3) . ? C21 H21B 1.00(3) . ? C21 H21C 0.91(3) . ? C21 H21A 1.00(3) . ? C26 C27 1.390(3) . ? C26 C31 1.401(3) . ? C27 C28 1.380(3) . ? C27 H27 0.94(2) . ? C28 C29 1.403(3) . ? C28 H28 0.97(2) . ? C29 C30 1.398(3) . ? C30 C31 1.377(3) . ? C30 H30 0.96(2) . ? C31 H31 0.96(2) . ? C33 H33A 1.06(3) . ? C33 H33B 0.98(3) . ? C33 H33C 1.00(2) . ? C34 H34A 1.06(3) . ? C34 H34B 0.97(2) . ? C34 H34C 1.03(3) . ? 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 C16 N19 C21 120.3(2) . . ? C16 N19 C20 120.4(2) . . ? C21 N19 C20 119.1(2) . . ? C29 N32 C33 120.1(2) . . ? C29 N32 C34 119.5(2) . . ? C33 N32 C34 119.7(2) . . ? C7 C1 C9 108.89(18) . . ? C7 C1 C6 110.16(18) . . ? C9 C1 C6 107.85(17) . . ? C7 C1 C2 110.88(17) . . ? C9 C1 C2 106.32(18) . . ? C6 C1 C2 112.56(18) . . ? C3 C2 C11 120.6(2) . . ? C3 C2 C1 124.98(19) . . ? C11 C2 C1 114.37(18) . . ? C2 C3 C13 121.80(19) . . ? C2 C3 C4 120.62(19) . . ? C13 C3 C4 117.52(18) . . ? C22 C4 C24 106.62(18) . . ? C22 C4 C3 109.67(17) . . ? C24 C4 C3 105.68(17) . . ? C22 C4 C5 110.03(18) . . ? C24 C4 C5 109.23(17) . . ? C3 C4 C5 115.19(18) . . ? C6 C5 C26 121.84(19) . . ? C6 C5 C4 120.25(19) . . ? C26 C5 C4 117.87(19) . . ? C5 C6 C1 125.7(2) . . ? C5 C6 H6 119.4(10) . . ? C1 C6 H6 114.5(10) . . ? N8 C7 C1 178.5(2) . . ? N10 C9 C1 174.0(2) . . ? N12 C11 C2 175.9(2) . . ? C14 C13 C18 118.4(2) . . ? C14 C13 C3 121.13(19) . . ? C18 C13 C3 120.4(2) . . ? C15 C14 C13 121.2(2) . . ? C15 C14 H14 116.9(14) . . ? C13 C14 H14 121.9(14) . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 117.6(13) . . ? C16 C15 H15 121.4(13) . . ? N19 C16 C15 120.8(2) . . ? N19 C16 C17 121.5(2) . . ? C15 C16 C17 117.7(2) . . ? C18 C17 C16 120.5(2) . . ? C18 C17 H17 119.0(13) . . ? C16 C17 H17 120.5(13) . . ? C17 C18 C13 121.3(2) . . ? C17 C18 H18 119.6(12) . . ? C13 C18 H18 119.1(12) . . ? N19 C20 H20B 109.1(13) . . ? N19 C20 H20C 107.2(14) . . ? H20B C20 H20C 114(2) . . ? N19 C20 H20A 113.4(15) . . ? H20B C20 H20A 108(2) . . ? H20C C20 H20A 105(2) . . ? N19 C21 H21B 113.5(15) . . ? N19 C21 H21C 106.9(16) . . ? H21B C21 H21C 109(2) . . ? N19 C21 H21A 110.7(15) . . ? H21B C21 H21A 104(2) . . ? H21C C21 H21A 113(2) . . ? N23 C22 C4 178.3(2) . . ? N25 C24 C4 179.6(3) . . ? C27 C26 C31 116.3(2) . . ? C27 C26 C5 124.2(2) . . ? C31 C26 C5 119.5(2) . . ? C28 C27 C26 122.3(2) . . ? C28 C27 H27 116.9(13) . . ? C26 C27 H27 120.8(13) . . ? C27 C28 C29 121.1(2) . . ? C27 C28 H28 120.1(12) . . ? C29 C28 H28 118.8(12) . . ? N32 C29 C30 121.5(2) . . ? N32 C29 C28 121.4(2) . . ? C30 C29 C28 117.1(2) . . ? C31 C30 C29 121.1(2) . . ? C31 C30 H30 117.5(14) . . ? C29 C30 H30 121.3(14) . . ? C30 C31 C26 122.2(2) . . ? C30 C31 H31 117.0(12) . . ? C26 C31 H31 120.6(12) . . ? N32 C33 H33A 111.4(13) . . ? N32 C33 H33B 109.2(14) . . ? H33A C33 H33B 105.2(19) . . ? N32 C33 H33C 111.0(11) . . ? H33A C33 H33C 109.9(17) . . ? H33B C33 H33C 110.0(18) . . ? N32 C34 H34A 108.0(13) . . ? N32 C34 H34B 107.4(14) . . ? H34A C34 H34B 113.4(19) . . ? N32 C34 H34C 111.8(14) . . ? H34A C34 H34C 108.2(19) . . ? H34B C34 H34C 108.1(19) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 50.31 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.177 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.034 data_1 _database_code_depnum_ccdc_archive 'CCDC 802217' #TrackingRef '- JJdeposit.cif' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H10 N6' _chemical_formula_sum 'C17 H10 N6' _chemical_formula_weight 298.30 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 Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+3/4' '-x, -y, z+1/2' 'y, -x, z+1/4' _cell_length_a 11.5737(3) _cell_length_b 11.5737(3) _cell_length_c 11.5001(5) _cell_angle_alpha 90.00(0) _cell_angle_beta 90.0(0) _cell_angle_gamma 90.00(0) _cell_volume 1540.43(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4479 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 26.40 _exptl_crystal_description cube _exptl_crystal_colour black _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9867 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10808 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.46 _reflns_number_total 8470 _reflns_number_gt 7672 _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 Platon _computing_publication_material OLEX2 _refine_special_details ; Three cyano groups disordered over two positions. Refined with partially restrained geometry. Disordered atoms refined isotropically. ; _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^)+(0.1000P)^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 refall _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(3) _refine_ls_number_reflns 3106 _refine_ls_number_parameters 241 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1535 _refine_ls_wR_factor_gt 0.1492 _refine_ls_goodness_of_fit_ref 1.228 _refine_ls_restrained_S_all 1.227 _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 -0.27362(17) 0.20644(18) 0.30277(19) 0.0278(5) Uani 1 1 d . . . N2 N 0.4398(2) 0.1391(2) -0.0086(4) 0.0655(11) Uani 1 1 d . A . N3 N 0.16427(19) -0.10136(18) 0.0524(3) 0.0399(6) Uani 1 1 d . A . N14 N 0.4054(5) 0.2472(6) 0.3029(5) 0.0391(14) Uiso 0.476(7) 1 d P A 2 N15 N 0.1066(5) 0.4486(5) -0.0748(6) 0.0299(13) Uiso 0.476(7) 1 d P A 2 N5 N 0.1286(5) 0.4287(4) -0.1070(5) 0.0317(12) Uiso 0.524(7) 1 d P A 1 N6 N 0.3927(5) 0.5670(5) 0.1154(5) 0.0187(16) Uiso 0.524(7) 1 d P A 1 N16 N 0.4092(7) 0.5567(7) 0.1069(8) 0.034(3) Uiso 0.476(7) 1 d P A 2 N4 N 0.3840(4) 0.2951(5) 0.3203(4) 0.0330(11) Uiso 0.524(7) 1 d P A 1 C1 C 0.0536(2) 0.20524(19) 0.1466(2) 0.0225(5) Uani 1 1 d . A . C2 C -0.02358(19) 0.11095(19) 0.1355(2) 0.0228(5) Uani 1 1 d . . . H2 H -0.001(2) 0.034(2) 0.093(2) 0.023(7) Uiso 1 1 d . . . C3 C -0.1304(2) 0.1111(2) 0.1846(2) 0.0244(5) Uani 1 1 d . . . H3 H -0.180(2) 0.044(2) 0.173(2) 0.020(6) Uiso 1 1 d . . . C4 C -0.17000(18) 0.20746(19) 0.2500(2) 0.0218(5) Uani 1 1 d . . . C5 C -0.0952(2) 0.3050(2) 0.2574(2) 0.0248(5) Uani 1 1 d . . . H5 H -0.122(2) 0.370(3) 0.298(3) 0.026(7) Uiso 1 1 d . . . C6 C 0.0106(2) 0.3028(2) 0.2071(2) 0.0266(5) Uani 1 1 d . . . H6 H 0.066(3) 0.380(2) 0.213(3) 0.032(8) Uiso 1 1 d . . . C7 C -0.3498(3) 0.1072(3) 0.2934(3) 0.0424(8) Uani 1 1 d . . . H7A H -0.310(4) 0.047(4) 0.317(5) 0.076(14) Uiso 1 1 d . . . H7B H -0.385(4) 0.097(4) 0.225(5) 0.064(12) Uiso 1 1 d . . . H7C H -0.414(3) 0.111(3) 0.353(3) 0.051(10) Uiso 1 1 d . . . C8 C -0.3111(2) 0.3035(3) 0.3743(3) 0.0377(7) Uani 1 1 d . . . H8A H -0.249(3) 0.314(3) 0.420(3) 0.038(8) Uiso 1 1 d . . . H8B H -0.328(3) 0.370(3) 0.321(3) 0.038(8) Uiso 1 1 d . . . H8C H -0.385(4) 0.295(3) 0.398(4) 0.059(10) Uiso 1 1 d . . . C9 C 0.1696(2) 0.20212(19) 0.1056(3) 0.0301(6) Uani 1 1 d . . . C10 C 0.2312(2) 0.10969(19) 0.0646(2) 0.0268(5) Uani 1 1 d . A . C11 C 0.3472(3) 0.1253(2) 0.0232(3) 0.0414(8) Uani 1 1 d . . . C12 C 0.1926(2) -0.0073(2) 0.0588(2) 0.0283(5) Uani 1 1 d . . . C13 C 0.2515(4) 0.3026(4) 0.1378(4) 0.0216(12) Uiso 0.524(7) 1 d PD A 1 C14 C 0.3249(6) 0.3026(5) 0.2410(6) 0.0306(15) Uiso 0.524(7) 1 d PD A 1 C15 C 0.2552(3) 0.3987(4) 0.0694(4) 0.0213(11) Uiso 0.524(7) 1 d PD A 1 C16 C 0.1833(6) 0.4093(5) -0.0327(6) 0.0287(16) Uiso 0.524(7) 1 d PD A 1 C17 C 0.3356(5) 0.4917(5) 0.0944(5) 0.0235(13) Uiso 0.524(7) 1 d PD A 1 C23 C 0.2149(4) 0.3199(4) 0.0761(5) 0.0262(14) Uiso 0.476(7) 1 d PD A 2 C24 C 0.1626(6) 0.3987(5) -0.0062(6) 0.0226(15) Uiso 0.476(7) 1 d PD A 2 C25 C 0.3066(4) 0.3607(4) 0.1385(5) 0.0246(14) Uiso 0.476(7) 1 d PD A 2 C26 C 0.3559(6) 0.2904(5) 0.2271(5) 0.0252(15) Uiso 0.476(7) 1 d PD A 2 C27 C 0.3556(6) 0.4728(6) 0.1184(6) 0.0263(15) Uiso 0.476(7) 1 d PD A 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 0.0225(9) 0.0324(11) 0.0285(11) -0.0074(9) 0.0009(8) -0.0025(8) N2 0.0463(15) 0.0250(11) 0.125(3) 0.0143(15) 0.0498(19) 0.0068(10) N3 0.0282(11) 0.0261(11) 0.0653(17) -0.0044(11) 0.0047(11) 0.0036(9) C1 0.0268(11) 0.0191(10) 0.0217(11) 0.0035(9) 0.0040(9) 0.0018(8) C2 0.0243(11) 0.0215(10) 0.0227(12) -0.0020(9) -0.0072(9) 0.0034(9) C3 0.0235(11) 0.0240(11) 0.0257(12) -0.0024(10) -0.0054(9) 0.0013(9) C4 0.0186(10) 0.0279(12) 0.0190(11) 0.0008(9) -0.0040(8) 0.0022(8) C5 0.0304(12) 0.0218(11) 0.0223(12) -0.0004(9) -0.0015(10) 0.0044(9) C6 0.0321(12) 0.0185(10) 0.0293(14) -0.0006(9) 0.0017(10) 0.0000(9) C7 0.0293(13) 0.0442(17) 0.054(2) -0.0117(15) 0.0113(14) -0.0086(12) C8 0.0241(13) 0.0469(17) 0.0422(18) -0.0189(14) 0.0095(12) 0.0005(12) C9 0.0329(13) 0.0192(11) 0.0382(14) -0.0018(10) 0.0101(11) -0.0012(9) C10 0.0244(11) 0.0198(10) 0.0360(13) -0.0005(10) 0.0056(10) 0.0014(9) C11 0.0379(15) 0.0199(11) 0.066(2) -0.0001(12) 0.0209(14) 0.0016(10) C12 0.0216(11) 0.0240(12) 0.0393(14) 0.0023(10) 0.0013(10) 0.0066(9) _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 C4 1.344(3) . ? N1 C7 1.452(3) . ? N1 C8 1.458(3) . ? N2 C11 1.144(4) . ? N3 C12 1.140(3) . ? N14 C26 1.157(8) . ? N15 C24 1.174(8) . ? N5 C16 1.087(7) . ? N6 C17 1.120(7) . ? N16 C27 1.160(10) . ? N4 C14 1.143(7) . ? C1 C2 1.416(3) . ? C1 C6 1.417(3) . ? C1 C9 1.424(3) . ? C2 C3 1.359(3) . ? C3 C4 1.421(3) . ? C4 C5 1.425(3) . ? C5 C6 1.355(4) . ? C9 C10 1.370(3) . ? C9 C23 1.499(5) . ? C9 C13 1.545(5) . ? C10 C12 1.427(3) . ? C10 C11 1.435(4) . ? C13 C15 1.363(6) . ? C13 C14 1.460(7) . ? C15 C16 1.444(7) . ? C15 C17 1.452(6) . ? C23 C25 1.365(7) . ? C23 C24 1.447(8) . ? C25 C26 1.424(7) . ? C25 C27 1.435(7) . ? 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 C4 N1 C7 121.0(2) . . ? C4 N1 C8 120.9(2) . . ? C7 N1 C8 118.1(2) . . ? C2 C1 C6 115.9(2) . . ? C2 C1 C9 123.1(2) . . ? C6 C1 C9 120.9(2) . . ? C3 C2 C1 122.3(2) . . ? C2 C3 C4 121.0(2) . . ? N1 C4 C3 121.3(2) . . ? N1 C4 C5 121.5(2) . . ? C3 C4 C5 117.2(2) . . ? C6 C5 C4 120.6(2) . . ? C5 C6 C1 122.8(2) . . ? C10 C9 C1 128.7(2) . . ? C10 C9 C23 116.8(3) . . ? C1 C9 C23 112.4(3) . . ? C10 C9 C13 110.6(3) . . ? C1 C9 C13 118.7(2) . . ? C23 C9 C13 32.4(2) . . ? C9 C10 C12 126.4(2) . . ? C9 C10 C11 120.2(2) . . ? C12 C10 C11 113.4(2) . . ? N2 C11 C10 179.0(4) . . ? N3 C12 C10 178.1(3) . . ? C15 C13 C14 116.8(4) . . ? C15 C13 C9 119.7(4) . . ? C14 C13 C9 123.5(4) . . ? N4 C14 C13 175.4(6) . . ? C13 C15 C16 121.4(4) . . ? C13 C15 C17 120.7(5) . . ? C16 C15 C17 117.9(5) . . ? N5 C16 C15 172.9(6) . . ? N6 C17 C15 176.3(6) . . ? C25 C23 C24 116.8(4) . . ? C25 C23 C9 117.8(4) . . ? C24 C23 C9 125.1(4) . . ? N15 C24 C23 168.9(6) . . ? C23 C25 C26 119.4(5) . . ? C23 C25 C27 122.4(5) . . ? C26 C25 C27 118.3(5) . . ? N14 C26 C25 170.1(6) . . ? N16 C27 C25 170.7(8) . . ? 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 C1 C2 C3 -3.2(3) . . . . ? C9 C1 C2 C3 173.7(3) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C7 N1 C4 C3 -0.9(4) . . . . ? C8 N1 C4 C3 177.0(2) . . . . ? C7 N1 C4 C5 179.2(3) . . . . ? C8 N1 C4 C5 -2.9(4) . . . . ? C2 C3 C4 N1 -177.3(2) . . . . ? C2 C3 C4 C5 2.6(3) . . . . ? N1 C4 C5 C6 177.7(2) . . . . ? C3 C4 C5 C6 -2.3(3) . . . . ? C4 C5 C6 C1 -0.9(4) . . . . ? C2 C1 C6 C5 3.6(4) . . . . ? C9 C1 C6 C5 -173.4(2) . . . . ? C2 C1 C9 C10 -9.3(5) . . . . ? C6 C1 C9 C10 167.4(3) . . . . ? C2 C1 C9 C23 153.4(3) . . . . ? C6 C1 C9 C23 -29.9(4) . . . . ? C2 C1 C9 C13 -171.2(3) . . . . ? C6 C1 C9 C13 5.4(4) . . . . ? C1 C9 C10 C12 -2.9(5) . . . . ? C23 C9 C10 C12 -165.0(3) . . . . ? C13 C9 C10 C12 160.2(3) . . . . ? C1 C9 C10 C11 177.8(3) . . . . ? C23 C9 C10 C11 15.8(5) . . . . ? C13 C9 C10 C11 -19.1(4) . . . . ? C9 C10 C11 N2 33(23) . . . . ? C12 C10 C11 N2 -146(23) . . . . ? C9 C10 C12 N3 169(10) . . . . ? C11 C10 C12 N3 -11(10) . . . . ? C10 C9 C13 C15 107.8(4) . . . . ? C1 C9 C13 C15 -87.2(4) . . . . ? C23 C9 C13 C15 -0.1(4) . . . . ? C10 C9 C13 C14 -73.8(5) . . . . ? C1 C9 C13 C14 91.2(5) . . . . ? C23 C9 C13 C14 178.3(8) . . . . ? C15 C13 C14 N4 -140(9) . . . . ? C9 C13 C14 N4 41(9) . . . . ? C14 C13 C15 C16 -178.0(5) . . . . ? C9 C13 C15 C16 0.6(7) . . . . ? C14 C13 C15 C17 4.7(7) . . . . ? C9 C13 C15 C17 -176.8(4) . . . . ? C13 C15 C16 N5 146(6) . . . . ? C17 C15 C16 N5 -36(6) . . . . ? C13 C15 C17 N6 -110(11) . . . . ? C16 C15 C17 N6 73(11) . . . . ? C10 C9 C23 C25 -78.0(5) . . . . ? C1 C9 C23 C25 117.1(4) . . . . ? C13 C9 C23 C25 8.5(4) . . . . ? C10 C9 C23 C24 108.0(6) . . . . ? C1 C9 C23 C24 -56.9(6) . . . . ? C13 C9 C23 C24 -165.5(8) . . . . ? C25 C23 C24 N15 -172(4) . . . . ? C9 C23 C24 N15 2(4) . . . . ? C24 C23 C25 C26 175.2(6) . . . . ? C9 C23 C25 C26 0.6(7) . . . . ? C24 C23 C25 C27 -4.7(8) . . . . ? C9 C23 C25 C27 -179.2(5) . . . . ? C23 C25 C26 N14 -173(4) . . . . ? C27 C25 C26 N14 7(5) . . . . ? C23 C25 C27 N16 -149(5) . . . . ? C26 C25 C27 N16 31(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.216 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.045