data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Stefan Brase' _publ_contact_author_email BRAESE@IOC.UKA.DE _publ_section_title ; Four-Fold Click Reactions: Generation of Tetrahedral Methane- and Adamantane-Based Building Blocks for Higher Molecular Assemblies ; loop_ _publ_author_name 'Stefan Brase' 'Thierry Muller' 'Martin Nieger' 'Oliver Plietzsch' 'Clemens Richert' 'Christine I. Schilling' ; M.Tolev ; # Attachment 'OBC_Plietzsch_CIF.CIF' data_sb107_hy_compound_1a _database_code_depnum_ccdc_archive 'CCDC 734783' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetrakis(4-(4-phenyl-1,2,3-triazol-1-yl)phenyl)methane ; _chemical_name_common Tetrakis(4-(4-phenyl-1,2,3-triazol-1-yl)phenyl)methane _chemical_melting_point ? _chemical_formula_moiety 'C57 H40 N12, 2 (C3 H7 N O)' _chemical_formula_sum 'C63 H54 N14 O2' _chemical_formula_weight 1039.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.701(6) _cell_length_b 8.996(2) _cell_length_c 20.844(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.53(2) _cell_angle_gamma 90.00 _cell_volume 5248.9(19) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description plates _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2184 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 480 sec./deg., 1 deg., 5 sets, 341 frames ; _diffrn_ambient_temperature 123(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-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20477 _diffrn_reflns_av_R_equivalents 0.0730 _diffrn_reflns_av_sigmaI/netI 0.0725 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4625 _reflns_number_gt 2835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The large anisotropic Uij values of the solvent dmf indicates a possible disorder, also the large max. and min. difference electron density (localized in the solvent). Use of L.S. restraints for the refinement of the geometry and the displacement parameters (DFIX, SADI, SIMU, DELU). ; _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^)+(0.0900P)^2^+24.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4625 _refine_ls_number_parameters 356 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.1413 _refine_ls_R_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.2309 _refine_ls_wR_factor_gt 0.1970 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0000 0.4888(7) 0.2500 0.0250(13) Uani 1 2 d S . . C1A C -0.00087(13) 0.3939(5) 0.3113(2) 0.0241(9) Uani 1 1 d . . . C2A C -0.02114(14) 0.4447(5) 0.3584(2) 0.0267(10) Uani 1 1 d . . . H2A H -0.0405 0.5315 0.3487 0.032 Uiso 1 1 calc R . . C3A C -0.01352(14) 0.3704(5) 0.4195(2) 0.0276(10) Uani 1 1 d . . . H3A H -0.0278 0.4061 0.4511 0.033 Uiso 1 1 calc R . . C4A C 0.01475(14) 0.2451(5) 0.4345(2) 0.0262(10) Uani 1 1 d . . . C5A C 0.03413(16) 0.1901(5) 0.3876(2) 0.0326(10) Uani 1 1 d . . . H5A H 0.0527 0.1017 0.3971 0.039 Uiso 1 1 calc R . . C6A C 0.02634(15) 0.2643(5) 0.3267(2) 0.0303(10) Uani 1 1 d . . . H6A H 0.0399 0.2262 0.2947 0.036 Uiso 1 1 calc R . . N7A N 0.02723(12) 0.1767(4) 0.49995(16) 0.0268(8) Uani 1 1 d . . . N8A N 0.00162(14) 0.2049(4) 0.54188(19) 0.0385(10) Uani 1 1 d . . . N9A N 0.02272(13) 0.1332(4) 0.59867(18) 0.0365(10) Uani 1 1 d . . . C10A C 0.06185(15) 0.0593(5) 0.5944(2) 0.0291(10) Uani 1 1 d . . . C11A C 0.06465(14) 0.0887(5) 0.5314(2) 0.0299(10) Uani 1 1 d . . . H11A H 0.0883 0.0540 0.5136 0.036 Uiso 1 1 calc R . . C12A C 0.09224(15) -0.0309(5) 0.6509(2) 0.0312(10) Uani 1 1 d . . . C13A C 0.12493(16) -0.1308(6) 0.6399(2) 0.0408(12) Uani 1 1 d . . . H13A H 0.1277 -0.1390 0.5960 0.049 Uiso 1 1 calc R . . C14A C 0.15327(17) -0.2177(6) 0.6926(3) 0.0466(13) Uani 1 1 d . . . H14A H 0.1747 -0.2873 0.6842 0.056 Uiso 1 1 calc R . . C15A C 0.15070(17) -0.2044(6) 0.7570(2) 0.0442(13) Uani 1 1 d . . . H15A H 0.1706 -0.2633 0.7932 0.053 Uiso 1 1 calc R . . C16A C 0.11900(17) -0.1049(6) 0.7687(2) 0.0399(12) Uani 1 1 d . . . H16A H 0.1173 -0.0947 0.8132 0.048 Uiso 1 1 calc R . . C17A C 0.08972(16) -0.0198(6) 0.7161(2) 0.0354(11) Uani 1 1 d . . . H17A H 0.0676 0.0470 0.7246 0.043 Uiso 1 1 calc R . . C1B C 0.04478(14) 0.5865(5) 0.2815(2) 0.0257(10) Uani 1 1 d . . . C2B C 0.09001(14) 0.5469(5) 0.2824(2) 0.0260(9) Uani 1 1 d . . . H2B H 0.0937 0.4623 0.2573 0.031 Uiso 1 1 calc R . . C3B C 0.13030(14) 0.6281(5) 0.3192(2) 0.0277(10) Uani 1 1 d . . . H3B H 0.1611 0.6003 0.3187 0.033 Uiso 1 1 calc R . . C4B C 0.12479(14) 0.7506(5) 0.3566(2) 0.0260(9) Uani 1 1 d . . . C5B C 0.07998(15) 0.7900(5) 0.3567(2) 0.0320(11) Uani 1 1 d . . . H5B H 0.0764 0.8726 0.3830 0.038 Uiso 1 1 calc R . . C6B C 0.04041(15) 0.7107(5) 0.3191(2) 0.0310(10) Uani 1 1 d . . . H6B H 0.0097 0.7409 0.3186 0.037 Uiso 1 1 calc R . . N7B N 0.16539(12) 0.8347(4) 0.39636(17) 0.0293(8) Uani 1 1 d . . . N8B N 0.15886(13) 0.9589(4) 0.4299(2) 0.0400(10) Uani 1 1 d . . . N9B N 0.20141(13) 1.0134(5) 0.46101(19) 0.0387(10) Uani 1 1 d . . . C10B C 0.23505(15) 0.9264(5) 0.4484(2) 0.0291(10) Uani 1 1 d . . . C11B C 0.21189(14) 0.8111(5) 0.4073(2) 0.0287(10) Uani 1 1 d . . . H11B H 0.2258 0.7320 0.3903 0.034 Uiso 1 1 calc R . . C12B C 0.28652(15) 0.9605(5) 0.4764(2) 0.0297(10) Uani 1 1 d . . . C13B C 0.31956(16) 0.8676(6) 0.4639(2) 0.0368(11) Uani 1 1 d . . . H13B H 0.3091 0.7811 0.4368 0.044 Uiso 1 1 calc R . . C14B C 0.36828(17) 0.9001(6) 0.4907(2) 0.0437(13) Uani 1 1 d . . . H14B H 0.3909 0.8358 0.4819 0.052 Uiso 1 1 calc R . . C15B C 0.38352(17) 1.0257(6) 0.5300(2) 0.0413(12) Uani 1 1 d . . . H15B H 0.4166 1.0479 0.5485 0.050 Uiso 1 1 calc R . . C16B C 0.35032(16) 1.1195(6) 0.5424(2) 0.0389(12) Uani 1 1 d . . . H16B H 0.3607 1.2068 0.5689 0.047 Uiso 1 1 calc R . . C17B C 0.30260(16) 1.0867(5) 0.5168(2) 0.0355(11) Uani 1 1 d . . . H17B H 0.2802 1.1504 0.5265 0.043 Uiso 1 1 calc R . . O1D O 0.24677(15) 0.5259(5) 0.3363(3) 0.0783(14) Uani 1 1 d DU . . C1D C 0.2763(2) 0.4110(9) 0.3647(4) 0.093(2) Uani 1 1 d DU . . H1D H 0.2857 0.3882 0.4119 0.111 Uiso 1 1 calc R . . N1D N 0.2898(2) 0.3396(7) 0.3251(3) 0.0818(16) Uani 1 1 d DU . . C11D C 0.28042(17) 0.3680(6) 0.2546(2) 0.0508(14) Uani 1 1 d DU . . H11C H 0.2481 0.4081 0.2345 0.076 Uiso 1 1 calc R . . H11D H 0.2831 0.2751 0.2315 0.076 Uiso 1 1 calc R . . H11E H 0.3036 0.4401 0.2493 0.076 Uiso 1 1 calc R . . C12D C 0.3237(3) 0.2055(7) 0.3510(2) 0.109(3) Uani 1 1 d RDU . . H12A H 0.3405 0.2159 0.4000 0.164 Uiso 1 1 calc R . . H12B H 0.3471 0.2023 0.3271 0.164 Uiso 1 1 calc R . . H12C H 0.3051 0.1133 0.3423 0.164 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 C1 0.020(3) 0.024(3) 0.031(3) 0.000 0.009(2) 0.000 C1A 0.021(2) 0.022(2) 0.029(2) -0.0040(18) 0.0076(17) -0.0027(18) C2A 0.020(2) 0.027(3) 0.032(2) -0.0019(19) 0.0083(18) 0.0017(18) C3A 0.022(2) 0.030(3) 0.032(2) -0.003(2) 0.0117(18) 0.0007(19) C4A 0.027(2) 0.025(2) 0.027(2) -0.0019(19) 0.0093(18) -0.0032(19) C5A 0.040(2) 0.023(3) 0.035(2) 0.001(2) 0.013(2) 0.006(2) C6A 0.035(2) 0.026(3) 0.032(2) -0.003(2) 0.0145(19) 0.004(2) N7A 0.0308(19) 0.025(2) 0.0255(18) -0.0042(15) 0.0108(15) -0.0022(16) N8A 0.047(2) 0.038(3) 0.036(2) 0.0014(19) 0.0210(19) 0.008(2) N9A 0.046(2) 0.035(2) 0.034(2) 0.0045(18) 0.0202(18) 0.0095(19) C10A 0.030(2) 0.026(3) 0.031(2) -0.005(2) 0.0096(19) -0.0042(19) C11A 0.024(2) 0.035(3) 0.030(2) -0.003(2) 0.0079(18) 0.001(2) C12A 0.031(2) 0.028(3) 0.035(2) -0.002(2) 0.0109(19) -0.007(2) C13A 0.043(3) 0.045(3) 0.032(2) -0.004(2) 0.010(2) 0.002(2) C14A 0.038(3) 0.043(3) 0.056(3) 0.007(3) 0.013(2) 0.010(2) C15A 0.036(3) 0.047(3) 0.043(3) 0.012(2) 0.004(2) -0.007(2) C16A 0.043(3) 0.042(3) 0.037(2) 0.006(2) 0.016(2) -0.009(2) C17A 0.035(2) 0.039(3) 0.034(2) 0.001(2) 0.013(2) -0.004(2) C1B 0.025(2) 0.022(2) 0.030(2) 0.0021(18) 0.0089(18) -0.0003(18) C2B 0.026(2) 0.022(2) 0.031(2) -0.0036(19) 0.0112(18) 0.0038(18) C3B 0.023(2) 0.030(3) 0.031(2) -0.002(2) 0.0100(18) 0.0038(19) C4B 0.023(2) 0.022(2) 0.031(2) -0.0014(19) 0.0056(18) -0.0020(17) C5B 0.032(2) 0.024(3) 0.044(3) -0.006(2) 0.018(2) 0.004(2) C6B 0.026(2) 0.026(3) 0.043(2) -0.005(2) 0.015(2) 0.0002(19) N7B 0.0301(19) 0.026(2) 0.0303(19) -0.0062(16) 0.0088(16) 0.0010(16) N8B 0.031(2) 0.034(2) 0.048(2) -0.014(2) 0.0047(18) 0.0005(18) N9B 0.030(2) 0.036(2) 0.045(2) -0.0105(19) 0.0061(18) -0.0008(18) C10B 0.029(2) 0.027(3) 0.031(2) 0.001(2) 0.0094(19) -0.0022(19) C11B 0.023(2) 0.031(3) 0.033(2) -0.002(2) 0.0098(18) -0.0043(19) C12B 0.033(2) 0.027(3) 0.028(2) 0.0031(19) 0.0090(19) -0.002(2) C13B 0.035(2) 0.033(3) 0.043(3) -0.007(2) 0.014(2) -0.005(2) C14B 0.036(3) 0.047(3) 0.051(3) -0.006(3) 0.018(2) -0.003(2) C15B 0.031(2) 0.046(3) 0.044(3) -0.003(2) 0.010(2) -0.011(2) C16B 0.037(3) 0.039(3) 0.038(3) -0.007(2) 0.008(2) -0.011(2) C17B 0.034(2) 0.033(3) 0.037(2) -0.002(2) 0.009(2) 0.001(2) O1D 0.058(3) 0.063(3) 0.129(4) 0.004(3) 0.051(3) 0.009(2) C1D 0.074(5) 0.120(6) 0.106(5) -0.042(5) 0.059(4) -0.041(4) N1D 0.088(4) 0.092(4) 0.076(3) -0.019(3) 0.041(3) -0.033(3) C11D 0.052(3) 0.062(4) 0.042(3) -0.008(3) 0.020(2) -0.016(3) C12D 0.099(6) 0.096(6) 0.122(7) 0.033(5) 0.021(5) 0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C1A 1.544(5) 2 ? C1 C1A 1.544(5) . ? C1 C1B 1.545(5) . ? C1 C1B 1.545(5) 2 ? C1A C2A 1.390(5) . ? C1A C6A 1.393(6) . ? C2A C3A 1.388(6) . ? C2A H2A 0.9500 . ? C3A C4A 1.378(6) . ? C3A H3A 0.9500 . ? C4A C5A 1.382(6) . ? C4A N7A 1.428(5) . ? C5A C6A 1.383(6) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? N7A C11A 1.343(5) . ? N7A N8A 1.361(5) . ? N8A N9A 1.309(5) . ? N9A C10A 1.367(5) . ? C10A C11A 1.369(6) . ? C10A C12A 1.466(6) . ? C11A H11A 0.9500 . ? C12A C17A 1.388(6) . ? C12A C13A 1.397(6) . ? C13A C14A 1.381(7) . ? C13A H13A 0.9500 . ? C14A C15A 1.376(7) . ? C14A H14A 0.9500 . ? C15A C16A 1.379(7) . ? C15A H15A 0.9500 . ? C16A C17A 1.381(6) . ? C16A H16A 0.9500 . ? C17A H17A 0.9500 . ? C1B C2B 1.384(5) . ? C1B C6B 1.395(6) . ? C2B C3B 1.393(6) . ? C2B H2B 0.9500 . ? C3B C4B 1.391(6) . ? C3B H3B 0.9500 . ? C4B C5B 1.378(6) . ? C4B N7B 1.430(5) . ? C5B C6B 1.375(6) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? N7B C11B 1.340(5) . ? N7B N8B 1.366(5) . ? N8B N9B 1.308(5) . ? N9B C10B 1.362(6) . ? C10B C11B 1.375(6) . ? C10B C12B 1.475(6) . ? C11B H11B 0.9500 . ? C12B C13B 1.379(6) . ? C12B C17B 1.399(6) . ? C13B C14B 1.397(6) . ? C13B H13B 0.9500 . ? C14B C15B 1.381(7) . ? C14B H14B 0.9500 . ? C15B C16B 1.386(7) . ? C15B H15B 0.9500 . ? C16B C17B 1.369(6) . ? C16B H16B 0.9500 . ? C17B H17B 0.9500 . ? O1D C1D 1.357(8) . ? C1D N1D 1.215(8) . ? C1D H1D 0.9500 . ? N1D C11D 1.425(7) . ? N1D C12D 1.548(8) . ? C11D H11C 0.9800 . ? C11D H11D 0.9800 . ? C11D H11E 0.9800 . ? C12D H12A 0.9800 . ? C12D H12B 0.9800 . ? C12D H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A C1 C1A 112.8(5) 2 . ? C1A C1 C1B 114.6(2) 2 . ? C1A C1 C1B 102.3(2) . . ? C1A C1 C1B 102.3(2) 2 2 ? C1A C1 C1B 114.6(2) . 2 ? C1B C1 C1B 110.7(5) . 2 ? C2A C1A C6A 117.8(4) . . ? C2A C1A C1 122.2(4) . . ? C6A C1A C1 119.0(3) . . ? C3A C2A C1A 120.9(4) . . ? C3A C2A H2A 119.5 . . ? C1A C2A H2A 119.5 . . ? C4A C3A C2A 120.1(4) . . ? C4A C3A H3A 119.9 . . ? C2A C3A H3A 119.9 . . ? C3A C4A C5A 119.9(4) . . ? C3A C4A N7A 120.9(4) . . ? C5A C4A N7A 119.0(4) . . ? C4A C5A C6A 119.6(4) . . ? C4A C5A H5A 120.2 . . ? C6A C5A H5A 120.2 . . ? C5A C6A C1A 121.5(4) . . ? C5A C6A H6A 119.3 . . ? C1A C6A H6A 119.3 . . ? C11A N7A N8A 110.2(3) . . ? C11A N7A C4A 129.0(3) . . ? N8A N7A C4A 120.7(3) . . ? N9A N8A N7A 106.7(3) . . ? N8A N9A C10A 110.0(3) . . ? N9A C10A C11A 107.1(4) . . ? N9A C10A C12A 121.7(4) . . ? C11A C10A C12A 131.3(4) . . ? N7A C11A C10A 106.1(4) . . ? N7A C11A H11A 127.0 . . ? C10A C11A H11A 127.0 . . ? C17A C12A C13A 118.3(4) . . ? C17A C12A C10A 121.8(4) . . ? C13A C12A C10A 119.9(4) . . ? C14A C13A C12A 120.4(4) . . ? C14A C13A H13A 119.8 . . ? C12A C13A H13A 119.8 . . ? C15A C14A C13A 120.6(5) . . ? C15A C14A H14A 119.7 . . ? C13A C14A H14A 119.7 . . ? C14A C15A C16A 119.5(5) . . ? C14A C15A H15A 120.2 . . ? C16A C15A H15A 120.2 . . ? C15A C16A C17A 120.4(4) . . ? C15A C16A H16A 119.8 . . ? C17A C16A H16A 119.8 . . ? C16A C17A C12A 120.8(5) . . ? C16A C17A H17A 119.6 . . ? C12A C17A H17A 119.6 . . ? C2B C1B C6B 118.1(4) . . ? C2B C1B C1 123.5(4) . . ? C6B C1B C1 117.8(3) . . ? C1B C2B C3B 121.5(4) . . ? C1B C2B H2B 119.2 . . ? C3B C2B H2B 119.2 . . ? C4B C3B C2B 118.9(4) . . ? C4B C3B H3B 120.5 . . ? C2B C3B H3B 120.5 . . ? C5B C4B C3B 120.0(4) . . ? C5B C4B N7B 119.4(4) . . ? C3B C4B N7B 120.6(4) . . ? C6B C5B C4B 120.5(4) . . ? C6B C5B H5B 119.8 . . ? C4B C5B H5B 119.8 . . ? C5B C6B C1B 120.9(4) . . ? C5B C6B H6B 119.5 . . ? C1B C6B H6B 119.5 . . ? C11B N7B N8B 110.9(3) . . ? C11B N7B C4B 129.5(4) . . ? N8B N7B C4B 119.5(3) . . ? N9B N8B N7B 106.4(3) . . ? N8B N9B C10B 109.8(4) . . ? N9B C10B C11B 107.9(4) . . ? N9B C10B C12B 122.3(4) . . ? C11B C10B C12B 129.8(4) . . ? N7B C11B C10B 105.0(4) . . ? N7B C11B H11B 127.5 . . ? C10B C11B H11B 127.5 . . ? C13B C12B C17B 119.0(4) . . ? C13B C12B C10B 120.5(4) . . ? C17B C12B C10B 120.5(4) . . ? C12B C13B C14B 120.3(4) . . ? C12B C13B H13B 119.8 . . ? C14B C13B H13B 119.8 . . ? C15B C14B C13B 120.0(5) . . ? C15B C14B H14B 120.0 . . ? C13B C14B H14B 120.0 . . ? C14B C15B C16B 119.8(4) . . ? C14B C15B H15B 120.1 . . ? C16B C15B H15B 120.1 . . ? C17B C16B C15B 120.3(5) . . ? C17B C16B H16B 119.9 . . ? C15B C16B H16B 119.9 . . ? C16B C17B C12B 120.7(4) . . ? C16B C17B H17B 119.7 . . ? C12B C17B H17B 119.7 . . ? N1D C1D O1D 114.8(7) . . ? N1D C1D H1D 122.6 . . ? O1D C1D H1D 122.6 . . ? C1D N1D C11D 127.6(7) . . ? C1D N1D C12D 120.0(6) . . ? C11D N1D C12D 112.3(5) . . ? N1D C11D H11C 109.5 . . ? N1D C11D H11D 109.5 . . ? H11C C11D H11D 109.5 . . ? N1D C11D H11E 109.5 . . ? H11C C11D H11E 109.5 . . ? H11D C11D H11E 109.5 . . ? N1D C12D H12A 109.5 . . ? N1D C12D H12B 109.5 . . ? H12A C12D H12B 109.5 . . ? N1D C12D H12C 109.5 . . ? H12A C12D H12C 109.5 . . ? H12B C12D H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A C1 C1A C2A -152.4(4) 2 . . . ? C1B C1 C1A C2A 84.0(4) . . . . ? C1B C1 C1A C2A -35.9(5) 2 . . . ? C1A C1 C1A C6A 38.7(3) 2 . . . ? C1B C1 C1A C6A -84.9(5) . . . . ? C1B C1 C1A C6A 155.3(4) 2 . . . ? C6A C1A C2A C3A 1.5(6) . . . . ? C1 C1A C2A C3A -167.5(3) . . . . ? C1A C2A C3A C4A 0.5(6) . . . . ? C2A C3A C4A C5A -2.4(6) . . . . ? C2A C3A C4A N7A 173.1(4) . . . . ? C3A C4A C5A C6A 2.2(6) . . . . ? N7A C4A C5A C6A -173.3(4) . . . . ? C4A C5A C6A C1A -0.2(7) . . . . ? C2A C1A C6A C5A -1.6(6) . . . . ? C1 C1A C6A C5A 167.8(4) . . . . ? C3A C4A N7A C11A -156.5(4) . . . . ? C5A C4A N7A C11A 19.0(6) . . . . ? C3A C4A N7A N8A 18.8(6) . . . . ? C5A C4A N7A N8A -165.6(4) . . . . ? C11A N7A N8A N9A -0.8(5) . . . . ? C4A N7A N8A N9A -177.0(4) . . . . ? N7A N8A N9A C10A 0.3(5) . . . . ? N8A N9A C10A C11A 0.3(5) . . . . ? N8A N9A C10A C12A -179.8(4) . . . . ? N8A N7A C11A C10A 1.0(5) . . . . ? C4A N7A C11A C10A 176.7(4) . . . . ? N9A C10A C11A N7A -0.8(5) . . . . ? C12A C10A C11A N7A 179.4(4) . . . . ? N9A C10A C12A C17A -14.8(7) . . . . ? C11A C10A C12A C17A 165.0(5) . . . . ? N9A C10A C12A C13A 165.4(4) . . . . ? C11A C10A C12A C13A -14.7(7) . . . . ? C17A C12A C13A C14A 1.1(7) . . . . ? C10A C12A C13A C14A -179.1(4) . . . . ? C12A C13A C14A C15A -1.8(8) . . . . ? C13A C14A C15A C16A 1.0(8) . . . . ? C14A C15A C16A C17A 0.5(7) . . . . ? C15A C16A C17A C12A -1.2(7) . . . . ? C13A C12A C17A C16A 0.4(7) . . . . ? C10A C12A C17A C16A -179.4(4) . . . . ? C1A C1 C1B C2B -31.4(5) 2 . . . ? C1A C1 C1B C2B 91.0(4) . . . . ? C1B C1 C1B C2B -146.5(4) 2 . . . ? C1A C1 C1B C6B 157.6(4) 2 . . . ? C1A C1 C1B C6B -80.0(5) . . . . ? C1B C1 C1B C6B 42.6(3) 2 . . . ? C6B C1B C2B C3B -0.3(6) . . . . ? C1 C1B C2B C3B -171.2(3) . . . . ? C1B C2B C3B C4B 0.9(6) . . . . ? C2B C3B C4B C5B -0.2(6) . . . . ? C2B C3B C4B N7B 178.5(4) . . . . ? C3B C4B C5B C6B -1.2(7) . . . . ? N7B C4B C5B C6B -179.9(4) . . . . ? C4B C5B C6B C1B 1.8(7) . . . . ? C2B C1B C6B C5B -1.1(6) . . . . ? C1 C1B C6B C5B 170.4(4) . . . . ? C5B C4B N7B C11B 175.2(4) . . . . ? C3B C4B N7B C11B -3.4(7) . . . . ? C5B C4B N7B N8B -4.6(6) . . . . ? C3B C4B N7B N8B 176.7(4) . . . . ? C11B N7B N8B N9B 0.8(5) . . . . ? C4B N7B N8B N9B -179.4(4) . . . . ? N7B N8B N9B C10B -0.3(5) . . . . ? N8B N9B C10B C11B -0.2(5) . . . . ? N8B N9B C10B C12B 179.6(4) . . . . ? N8B N7B C11B C10B -0.8(5) . . . . ? C4B N7B C11B C10B 179.3(4) . . . . ? N9B C10B C11B N7B 0.6(5) . . . . ? C12B C10B C11B N7B -179.2(4) . . . . ? N9B C10B C12B C13B 178.4(4) . . . . ? C11B C10B C12B C13B -1.8(7) . . . . ? N9B C10B C12B C17B -0.9(6) . . . . ? C11B C10B C12B C17B 178.8(4) . . . . ? C17B C12B C13B C14B -0.5(7) . . . . ? C10B C12B C13B C14B -179.8(4) . . . . ? C12B C13B C14B C15B 0.0(7) . . . . ? C13B C14B C15B C16B -0.3(7) . . . . ? C14B C15B C16B C17B 1.0(7) . . . . ? C15B C16B C17B C12B -1.5(7) . . . . ? C13B C12B C17B C16B 1.2(6) . . . . ? C10B C12B C17B C16B -179.4(4) . . . . ? O1D C1D N1D C11D 3.8(10) . . . . ? O1D C1D N1D C12D 180.0(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C3B H3B O1D 0.95 2.54 3.480(6) 171.6 . C11B H11B O1D 0.95 2.36 3.296(6) 170.1 . C6B H6B N9A 0.95 2.51 3.252(5) 135.3 5_566 C11D H11D O1D 0.98 2.64 3.562(7) 156.7 4_545 C1D H1D N9B 0.95 2.70 3.534(8) 147.3 7_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.173 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.072 #============================================================================== data_sb115_hy_compound_4a _database_code_depnum_ccdc_archive 'CCDC 734784' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,5,7-Tetrakis(4-(1-phenyl-1,2,3-triazol-4-yl)phenyl)adamantane ; _chemical_name_common ;1,3,5,7-Tetrakis(4-(1-phenyl-1,2,3-triazol-4- yl)phenyl)adamantane ; _chemical_melting_point ? _chemical_formula_moiety 'C70 H56 Cl12 N12' _chemical_formula_sum 'C70 H56 Cl12 N12' _chemical_formula_weight 1490.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P -4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' _cell_length_a 21.970(3) _cell_length_b 21.970(3) _cell_length_c 6.972(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3365.3(8) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 133 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 0.547 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7900 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; dx = 45 mm, 60 sec./deg., 1 deg., 3 sets, 261 frames ; _diffrn_ambient_temperature 123(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-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17869 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7550 _reflns_number_gt 6482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0693P)^2^+1.7506P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(6) _refine_ls_number_reflns 7550 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 0.53528(12) 0.42741(12) 1.0018(4) 0.0138(5) Uani 1 1 d . . . H1A H 0.5699 0.4142 0.9212 0.017 Uiso 1 1 calc R . . H1B H 0.5234 0.3929 1.0849 0.017 Uiso 1 1 calc R . . C2 C 0.48147(12) 0.44511(12) 0.8728(4) 0.0134(5) Uani 1 1 d . . . C3 C 0.5000 0.5000 0.7483(5) 0.0138(7) Uani 1 2 d S . . H3A H 0.5345 0.4883 0.6648 0.017 Uiso 0.50 1 calc PR . . H3B H 0.4655 0.5117 0.6648 0.017 Uiso 0.50 1 calc PR . . C4 C 0.46494(13) 0.39251(12) 0.7382(4) 0.0143(5) Uani 1 1 d . . . C5 C 0.40721(13) 0.36658(13) 0.7305(4) 0.0192(6) Uani 1 1 d . . . H5 H 0.3771 0.3791 0.8201 0.023 Uiso 1 1 calc R . . C6 C 0.39256(13) 0.32245(14) 0.5939(4) 0.0209(6) Uani 1 1 d . . . H6 H 0.3527 0.3056 0.5908 0.025 Uiso 1 1 calc R . . C7 C 0.43615(13) 0.30302(13) 0.4620(4) 0.0186(6) Uani 1 1 d . . . C8 C 0.49489(13) 0.32694(13) 0.4750(4) 0.0182(5) Uani 1 1 d . . . H8 H 0.5256 0.3129 0.3900 0.022 Uiso 1 1 calc R . . C9 C 0.50888(13) 0.37098(13) 0.6108(4) 0.0165(5) Uani 1 1 d . . . H9 H 0.5491 0.3867 0.6171 0.020 Uiso 1 1 calc R . . C10 C 0.42149(13) 0.25871(13) 0.3118(4) 0.0200(6) Uani 1 1 d . . . N11 N 0.36862(13) 0.22712(13) 0.3083(4) 0.0272(6) Uani 1 1 d . . . N12 N 0.36791(12) 0.19116(13) 0.1578(4) 0.0271(6) Uani 1 1 d . . . N13 N 0.42105(12) 0.19989(12) 0.0654(4) 0.0237(5) Uani 1 1 d . . . C14 C 0.45487(14) 0.24159(15) 0.1564(4) 0.0263(7) Uani 1 1 d . . . H14 H 0.4939 0.2561 0.1202 0.032 Uiso 1 1 calc R . . C15 C 0.43568(15) 0.16419(14) -0.1006(4) 0.0252(6) Uani 1 1 d . . . C16 C 0.39266(17) 0.15229(16) -0.2358(5) 0.0327(7) Uani 1 1 d . . . H16 H 0.3530 0.1692 -0.2242 0.039 Uiso 1 1 calc R . . C17 C 0.40699(18) 0.11543(18) -0.3906(5) 0.0386(9) Uani 1 1 d . . . H17 H 0.3771 0.1069 -0.4853 0.046 Uiso 1 1 calc R . . C18 C 0.46408(19) 0.0913(2) -0.4070(6) 0.0439(10) Uani 1 1 d . . . H18 H 0.4740 0.0665 -0.5142 0.053 Uiso 1 1 calc R . . C19 C 0.50754(19) 0.1029(2) -0.2680(6) 0.0483(10) Uani 1 1 d . . . H19 H 0.5469 0.0853 -0.2785 0.058 Uiso 1 1 calc R . . C20 C 0.49380(17) 0.1399(2) -0.1145(5) 0.0412(9) Uani 1 1 d . . . H20 H 0.5236 0.1486 -0.0197 0.049 Uiso 1 1 calc R . . C1' C -0.04393(12) 0.06771(11) 0.4998(4) 0.0124(5) Uani 1 1 d . . . H1'1 H -0.0798 0.0760 0.5817 0.015 Uiso 1 1 calc R . . H1'2 H -0.0369 0.1039 0.4180 0.015 Uiso 1 1 calc R . . C2' C 0.01230(11) 0.05690(12) 0.6278(3) 0.0118(5) Uani 1 1 d . . . C3' C 0.0000 0.0000 0.7496(5) 0.0115(6) Uani 1 2 d S . . H3'1 H 0.0356 -0.0077 0.8333 0.014 Uiso 0.50 1 calc PR . . H3'2 H -0.0356 0.0077 0.8333 0.014 Uiso 0.50 1 calc PR . . C4' C 0.02185(12) 0.11083(12) 0.7618(4) 0.0133(5) Uani 1 1 d . . . C5' C -0.02073(12) 0.12405(12) 0.9019(4) 0.0135(5) Uani 1 1 d . . . H5' H -0.0573 0.1010 0.9064 0.016 Uiso 1 1 calc R . . C6' C -0.01180(13) 0.16965(12) 1.0352(4) 0.0167(5) Uani 1 1 d . . . H6' H -0.0424 0.1779 1.1279 0.020 Uiso 1 1 calc R . . C7' C 0.04176(13) 0.20365(13) 1.0348(4) 0.0171(5) Uani 1 1 d . . . C8' C 0.08459(14) 0.19221(13) 0.8904(4) 0.0191(6) Uani 1 1 d . . . H8' H 0.1208 0.2158 0.8840 0.023 Uiso 1 1 calc R . . C9' C 0.07435(13) 0.14681(12) 0.7572(4) 0.0168(5) Uani 1 1 d . . . H9' H 0.1038 0.1398 0.6597 0.020 Uiso 1 1 calc R . . C10' C 0.05131(13) 0.25029(13) 1.1817(4) 0.0194(6) Uani 1 1 d . . . N11' N 0.08967(12) 0.29838(12) 1.1606(4) 0.0261(6) Uani 1 1 d . . . N12' N 0.08528(13) 0.33328(12) 1.3125(4) 0.0285(6) Uani 1 1 d . . . N13' N 0.04499(12) 0.30732(12) 1.4329(4) 0.0235(5) Uani 1 1 d . . . C14' C 0.02302(14) 0.25563(15) 1.3572(4) 0.0248(6) Uani 1 1 d . . . H14' H -0.0058 0.2286 1.4126 0.030 Uiso 1 1 calc R . . C15' C 0.02743(16) 0.33653(16) 1.6100(5) 0.0287(7) Uani 1 1 d . . . C16' C 0.0542(2) 0.39015(18) 1.6592(6) 0.0450(10) Uani 1 1 d . . . H16' H 0.0859 0.4071 1.5834 0.054 Uiso 1 1 calc R . . C17' C 0.0335(2) 0.41967(19) 1.8258(6) 0.0508(11) Uani 1 1 d . . . H17' H 0.0510 0.4575 1.8619 0.061 Uiso 1 1 calc R . . C18' C -0.0113(2) 0.3952(2) 1.9360(5) 0.0455(10) Uani 1 1 d . . . H18' H -0.0247 0.4158 2.0480 0.055 Uiso 1 1 calc R . . C19' C -0.03654(18) 0.3415(2) 1.8862(5) 0.0408(9) Uani 1 1 d . . . H19' H -0.0675 0.3244 1.9643 0.049 Uiso 1 1 calc R . . C20' C -0.01773(16) 0.31079(18) 1.7210(5) 0.0336(8) Uani 1 1 d . . . H20' H -0.0356 0.2730 1.6860 0.040 Uiso 1 1 calc R . . C1C C 0.23387(15) 0.18739(16) 0.4320(5) 0.0299(7) Uani 1 1 d . . . H1C H 0.2759 0.1976 0.3875 0.036 Uiso 1 1 calc R . . Cl1 Cl 0.23849(4) 0.14120(5) 0.63968(15) 0.0435(2) Uani 1 1 d . . . Cl2 Cl 0.19528(5) 0.25429(4) 0.48569(14) 0.0457(2) Uani 1 1 d . . . Cl3 Cl 0.19589(5) 0.14716(5) 0.25084(15) 0.0514(3) Uani 1 1 d . . . C2C C 0.22477(17) 0.34553(16) 1.0112(5) 0.0348(7) Uani 1 1 d . . . H2C H 0.1833 0.3368 1.0639 0.042 Uiso 1 1 calc R . . Cl4 Cl 0.21714(6) 0.38175(5) 0.78442(15) 0.0508(3) Uani 1 1 d . . . Cl5 Cl 0.26304(6) 0.39413(6) 1.16780(17) 0.0579(3) Uani 1 1 d . . . Cl6 Cl 0.26379(6) 0.27698(5) 0.98139(15) 0.0518(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0155(12) 0.0160(12) 0.0099(11) -0.0016(10) 0.0016(10) 0.0017(10) C2 0.0173(13) 0.0144(12) 0.0086(11) -0.0006(9) 0.0003(10) -0.0009(10) C3 0.0137(17) 0.0178(18) 0.0098(15) 0.000 0.000 -0.0022(15) C4 0.0219(13) 0.0122(12) 0.0088(11) 0.0004(9) -0.0019(10) -0.0014(10) C5 0.0195(14) 0.0204(14) 0.0176(13) -0.0028(11) 0.0039(10) -0.0009(11) C6 0.0172(14) 0.0222(14) 0.0231(14) -0.0032(12) 0.0020(11) -0.0057(11) C7 0.0201(14) 0.0167(13) 0.0191(14) -0.0033(11) -0.0020(10) -0.0014(11) C8 0.0197(13) 0.0237(14) 0.0114(12) -0.0045(11) 0.0022(10) -0.0001(11) C9 0.0174(13) 0.0169(13) 0.0153(12) -0.0017(10) -0.0004(10) -0.0006(10) C10 0.0189(14) 0.0206(14) 0.0205(14) -0.0031(11) -0.0004(11) -0.0021(11) N11 0.0256(14) 0.0266(14) 0.0294(14) -0.0086(11) 0.0008(11) -0.0066(11) N12 0.0216(13) 0.0284(14) 0.0312(14) -0.0136(11) 0.0020(11) -0.0054(11) N13 0.0215(13) 0.0269(14) 0.0227(12) -0.0102(10) -0.0018(10) -0.0012(10) C14 0.0233(15) 0.0301(16) 0.0255(15) -0.0115(13) -0.0004(12) -0.0083(13) C15 0.0264(16) 0.0251(16) 0.0241(15) -0.0112(12) -0.0023(12) -0.0019(13) C16 0.0331(18) 0.0322(18) 0.0329(18) -0.0093(14) -0.0069(14) 0.0027(14) C17 0.043(2) 0.042(2) 0.0305(18) -0.0124(16) -0.0091(15) -0.0001(17) C18 0.048(2) 0.051(2) 0.0326(19) -0.0247(17) 0.0002(16) -0.0003(19) C19 0.0303(19) 0.063(3) 0.052(2) -0.022(2) 0.0045(18) 0.0036(18) C20 0.0298(19) 0.056(2) 0.038(2) -0.0159(18) -0.0035(16) -0.0041(17) C1' 0.0146(12) 0.0119(11) 0.0107(11) -0.0004(10) -0.0026(10) 0.0003(9) C2' 0.0108(11) 0.0161(12) 0.0087(11) -0.0003(9) -0.0003(9) 0.0001(9) C3' 0.0164(18) 0.0107(17) 0.0074(14) 0.000 0.000 0.0000(14) C4' 0.0164(13) 0.0124(12) 0.0111(11) 0.0005(9) -0.0027(10) -0.0007(10) C5' 0.0142(12) 0.0138(12) 0.0126(11) 0.0004(10) -0.0013(9) -0.0008(10) C6' 0.0195(13) 0.0167(13) 0.0138(13) -0.0017(10) 0.0020(10) 0.0030(10) C7' 0.0211(13) 0.0153(13) 0.0149(13) -0.0025(10) -0.0016(10) 0.0004(10) C8' 0.0222(14) 0.0173(13) 0.0178(13) -0.0032(10) 0.0012(11) -0.0045(11) C9' 0.0188(13) 0.0174(13) 0.0142(12) -0.0003(10) 0.0034(10) -0.0001(10) C10' 0.0192(14) 0.0177(14) 0.0214(14) -0.0017(11) -0.0015(11) 0.0003(11) N11' 0.0288(14) 0.0223(13) 0.0272(13) -0.0073(11) 0.0025(11) -0.0035(10) N12' 0.0344(15) 0.0219(13) 0.0291(14) -0.0097(11) -0.0020(12) -0.0022(11) N13' 0.0237(13) 0.0254(13) 0.0215(12) -0.0081(10) -0.0038(10) 0.0015(10) C14' 0.0264(16) 0.0261(15) 0.0218(14) -0.0078(12) 0.0008(12) -0.0037(12) C15' 0.0334(18) 0.0296(17) 0.0231(15) -0.0123(13) -0.0079(13) 0.0108(14) C16' 0.070(3) 0.034(2) 0.0315(18) -0.0110(16) 0.0029(19) -0.0105(19) C17' 0.078(3) 0.033(2) 0.041(2) -0.0181(18) 0.003(2) -0.005(2) C18' 0.060(3) 0.047(2) 0.0297(18) -0.0150(17) -0.0032(17) 0.020(2) C19' 0.037(2) 0.060(3) 0.0253(16) -0.0065(16) 0.0016(15) 0.0188(18) C20' 0.0323(18) 0.045(2) 0.0237(15) -0.0101(14) -0.0046(13) 0.0089(15) C1C 0.0243(16) 0.0290(17) 0.0363(17) -0.0048(14) 0.0020(13) -0.0071(13) Cl1 0.0322(5) 0.0413(5) 0.0569(6) 0.0131(4) -0.0014(4) 0.0009(4) Cl2 0.0602(6) 0.0355(5) 0.0415(5) -0.0024(4) 0.0004(4) 0.0113(4) Cl3 0.0522(6) 0.0494(6) 0.0526(6) -0.0188(5) -0.0047(5) -0.0158(5) C2C 0.0366(19) 0.0312(18) 0.0365(18) -0.0020(15) 0.0057(16) -0.0023(14) Cl4 0.0731(8) 0.0320(5) 0.0473(5) 0.0015(4) -0.0004(5) 0.0063(5) Cl5 0.0637(7) 0.0555(7) 0.0544(6) -0.0166(5) -0.0068(5) -0.0125(5) Cl6 0.0694(7) 0.0389(5) 0.0470(5) 0.0053(4) 0.0066(5) 0.0146(5) _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 C1 C2 1.536(4) . ? C1 C2 1.536(3) 4_657 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C4 1.532(3) . ? C2 C1 1.536(3) 3_567 ? C2 C3 1.541(3) . ? C3 C2 1.541(3) 2_665 ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.391(4) . ? C4 C9 1.394(4) . ? C5 C6 1.397(4) . ? C5 H5 0.9500 . ? C6 C7 1.395(4) . ? C6 H6 0.9500 . ? C7 C8 1.396(4) . ? C7 C10 1.466(4) . ? C8 C9 1.388(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 N11 1.353(4) . ? C10 C14 1.361(4) . ? N11 N12 1.313(4) . ? N12 N13 1.347(4) . ? N13 C14 1.339(4) . ? N13 C15 1.435(4) . ? C14 H14 0.9500 . ? C15 C16 1.360(5) . ? C15 C20 1.387(5) . ? C16 C17 1.385(5) . ? C16 H16 0.9500 . ? C17 C18 1.366(6) . ? C17 H17 0.9500 . ? C18 C19 1.384(6) . ? C18 H18 0.9500 . ? C19 C20 1.377(5) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C1' C2' 1.534(3) 4_556 ? C1' C2' 1.543(3) . ? C1' H1'1 0.9900 . ? C1' H1'2 0.9900 . ? C2' C4' 1.523(4) . ? C2' C1' 1.534(3) 3_556 ? C2' C3' 1.535(3) . ? C3' C2' 1.535(3) 2 ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4' C5' 1.383(4) . ? C4' C9' 1.399(4) . ? C5' C6' 1.381(4) . ? C5' H5' 0.9500 . ? C6' C7' 1.394(4) . ? C6' H6' 0.9500 . ? C7' C8' 1.401(4) . ? C7' C10' 1.464(4) . ? C8' C9' 1.381(4) . ? C8' H8' 0.9500 . ? C9' H9' 0.9500 . ? C10' N11' 1.360(4) . ? C10' C14' 1.377(4) . ? N11' N12' 1.311(4) . ? N12' N13' 1.347(4) . ? N13' C14' 1.342(4) . ? N13' C15' 1.444(4) . ? C14' H14' 0.9500 . ? C15' C16' 1.360(5) . ? C15' C20' 1.380(5) . ? C16' C17' 1.406(6) . ? C16' H16' 0.9500 . ? C17' C18' 1.359(7) . ? C17' H17' 0.9500 . ? C18' C19' 1.347(6) . ? C18' H18' 0.9500 . ? C19' C20' 1.398(5) . ? C19' H19' 0.9500 . ? C20' H20' 0.9500 . ? C1C Cl2 1.738(4) . ? C1C Cl3 1.753(3) . ? C1C Cl1 1.771(4) . ? C1C H1C 1.0000 . ? C2C Cl5 1.743(4) . ? C2C Cl6 1.745(4) . ? C2C Cl4 1.778(4) . ? C2C H2C 1.0000 . ? 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 C2 C1 C2 110.7(2) . 4_657 ? C2 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 4_657 . ? C2 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 4_657 . ? H1A C1 H1B 108.1 . . ? C4 C2 C1 110.5(2) . . ? C4 C2 C1 112.1(2) . 3_567 ? C1 C2 C1 109.44(18) . 3_567 ? C4 C2 C3 107.9(2) . . ? C1 C2 C3 109.0(2) . . ? C1 C2 C3 107.78(19) 3_567 . ? C2 C3 C2 111.4(3) 2_665 . ? C2 C3 H3A 109.3 2_665 . ? C2 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 2_665 . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C9 117.9(2) . . ? C5 C4 C2 123.2(2) . . ? C9 C4 C2 118.8(2) . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 118.5(3) . . ? C6 C7 C10 121.6(3) . . ? C8 C7 C10 120.0(3) . . ? C9 C8 C7 120.8(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C4 121.2(3) . . ? C8 C9 H9 119.4 . . ? C4 C9 H9 119.4 . . ? N11 C10 C14 107.8(3) . . ? N11 C10 C7 122.8(3) . . ? C14 C10 C7 129.3(3) . . ? N12 N11 C10 109.5(3) . . ? N11 N12 N13 106.6(2) . . ? C14 N13 N12 110.6(2) . . ? C14 N13 C15 129.2(3) . . ? N12 N13 C15 120.2(2) . . ? N13 C14 C10 105.5(3) . . ? N13 C14 H14 127.3 . . ? C10 C14 H14 127.3 . . ? C16 C15 C20 121.2(3) . . ? C16 C15 N13 120.6(3) . . ? C20 C15 N13 118.2(3) . . ? C15 C16 C17 119.6(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 120.0(3) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.2(3) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 120.1(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C15 118.9(3) . . ? C19 C20 H20 120.6 . . ? C15 C20 H20 120.6 . . ? C2' C1' C2' 111.2(2) 4_556 . ? C2' C1' H1'1 109.4 4_556 . ? C2' C1' H1'1 109.4 . . ? C2' C1' H1'2 109.4 4_556 . ? C2' C1' H1'2 109.4 . . ? H1'1 C1' H1'2 108.0 . . ? C4' C2' C1' 113.0(2) . 3_556 ? C4' C2' C3' 108.6(2) . . ? C1' C2' C3' 108.02(19) 3_556 . ? C4' C2' C1' 110.2(2) . . ? C1' C2' C1' 109.17(17) 3_556 . ? C3' C2' C1' 107.73(19) . . ? C2' C3' C2' 112.8(3) 2 . ? C2' C3' H3'1 109.0 2 . ? C2' C3' H3'1 109.0 . . ? C2' C3' H3'2 109.0 2 . ? C2' C3' H3'2 109.0 . . ? H3'1 C3' H3'2 107.8 . . ? C5' C4' C9' 117.1(2) . . ? C5' C4' C2' 120.2(2) . . ? C9' C4' C2' 122.6(2) . . ? C6' C5' C4' 122.1(2) . . ? C6' C5' H5' 118.9 . . ? C4' C5' H5' 118.9 . . ? C5' C6' C7' 120.5(3) . . ? C5' C6' H6' 119.7 . . ? C7' C6' H6' 119.7 . . ? C6' C7' C8' 118.2(2) . . ? C6' C7' C10' 119.7(2) . . ? C8' C7' C10' 122.2(3) . . ? C9' C8' C7' 120.2(3) . . ? C9' C8' H8' 119.9 . . ? C7' C8' H8' 119.9 . . ? C8' C9' C4' 121.8(3) . . ? C8' C9' H9' 119.1 . . ? C4' C9' H9' 119.1 . . ? N11' C10' C14' 108.0(3) . . ? N11' C10' C7' 123.8(3) . . ? C14' C10' C7' 128.1(3) . . ? N12' N11' C10' 108.7(3) . . ? N11' N12' N13' 107.7(2) . . ? C14' N13' N12' 110.5(2) . . ? C14' N13' C15' 128.0(3) . . ? N12' N13' C15' 121.4(3) . . ? N13' C14' C10' 105.0(3) . . ? N13' C14' H14' 127.5 . . ? C10' C14' H14' 127.5 . . ? C16' C15' C20' 121.6(3) . . ? C16' C15' N13' 119.0(3) . . ? C20' C15' N13' 119.3(3) . . ? C15' C16' C17' 117.9(4) . . ? C15' C16' H16' 121.1 . . ? C17' C16' H16' 121.1 . . ? C18' C17' C16' 121.2(4) . . ? C18' C17' H17' 119.4 . . ? C16' C17' H17' 119.4 . . ? C19' C18' C17' 119.9(3) . . ? C19' C18' H18' 120.1 . . ? C17' C18' H18' 120.1 . . ? C18' C19' C20' 120.9(4) . . ? C18' C19' H19' 119.6 . . ? C20' C19' H19' 119.6 . . ? C15' C20' C19' 118.5(4) . . ? C15' C20' H20' 120.8 . . ? C19' C20' H20' 120.8 . . ? Cl2 C1C Cl3 110.4(2) . . ? Cl2 C1C Cl1 109.68(19) . . ? Cl3 C1C Cl1 109.11(19) . . ? Cl2 C1C H1C 109.2 . . ? Cl3 C1C H1C 109.2 . . ? Cl1 C1C H1C 109.2 . . ? Cl5 C2C Cl6 111.5(2) . . ? Cl5 C2C Cl4 109.2(2) . . ? Cl6 C2C Cl4 109.1(2) . . ? Cl5 C2C H2C 109.0 . . ? Cl6 C2C H2C 109.0 . . ? Cl4 C2C H2C 109.0 . . ? 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 C2 C1 C2 C4 176.1(2) 4_657 . . . ? C2 C1 C2 C1 -60.0(2) 4_657 . . 3_567 ? C2 C1 C2 C3 57.6(3) 4_657 . . . ? C4 C2 C3 C2 -179.0(2) . . . 2_665 ? C1 C2 C3 C2 -58.97(16) . . . 2_665 ? C1 C2 C3 C2 59.70(16) 3_567 . . 2_665 ? C1 C2 C4 C5 123.2(3) . . . . ? C1 C2 C4 C5 0.8(4) 3_567 . . . ? C3 C2 C4 C5 -117.8(3) . . . . ? C1 C2 C4 C9 -59.6(3) . . . . ? C1 C2 C4 C9 178.0(2) 3_567 . . . ? C3 C2 C4 C9 59.4(3) . . . . ? C9 C4 C5 C6 -3.0(4) . . . . ? C2 C4 C5 C6 174.2(3) . . . . ? C4 C5 C6 C7 0.5(4) . . . . ? C5 C6 C7 C8 2.4(4) . . . . ? C5 C6 C7 C10 -177.4(3) . . . . ? C6 C7 C8 C9 -2.8(4) . . . . ? C10 C7 C8 C9 177.1(3) . . . . ? C7 C8 C9 C4 0.1(4) . . . . ? C5 C4 C9 C8 2.7(4) . . . . ? C2 C4 C9 C8 -174.6(2) . . . . ? C6 C7 C10 N11 -10.3(5) . . . . ? C8 C7 C10 N11 169.9(3) . . . . ? C6 C7 C10 C14 169.3(3) . . . . ? C8 C7 C10 C14 -10.5(5) . . . . ? C14 C10 N11 N12 0.1(4) . . . . ? C7 C10 N11 N12 179.8(3) . . . . ? C10 N11 N12 N13 0.3(4) . . . . ? N11 N12 N13 C14 -0.5(4) . . . . ? N11 N12 N13 C15 176.4(3) . . . . ? N12 N13 C14 C10 0.6(4) . . . . ? C15 N13 C14 C10 -176.0(3) . . . . ? N11 C10 C14 N13 -0.4(4) . . . . ? C7 C10 C14 N13 179.9(3) . . . . ? C14 N13 C15 C16 -141.7(4) . . . . ? N12 N13 C15 C16 42.0(5) . . . . ? C14 N13 C15 C20 41.3(5) . . . . ? N12 N13 C15 C20 -135.0(4) . . . . ? C20 C15 C16 C17 -0.2(6) . . . . ? N13 C15 C16 C17 -177.1(3) . . . . ? C15 C16 C17 C18 -0.1(6) . . . . ? C16 C17 C18 C19 0.9(7) . . . . ? C17 C18 C19 C20 -1.4(7) . . . . ? C18 C19 C20 C15 1.1(7) . . . . ? C16 C15 C20 C19 -0.3(6) . . . . ? N13 C15 C20 C19 176.6(4) . . . . ? C2' C1' C2' C4' -176.5(2) 4_556 . . . ? C2' C1' C2' C1' 58.88(19) 4_556 . . 3_556 ? C2' C1' C2' C3' -58.2(3) 4_556 . . . ? C4' C2' C3' C2' 178.2(2) . . . 2 ? C1' C2' C3' C2' -58.94(15) 3_556 . . 2 ? C1' C2' C3' C2' 58.87(15) . . . 2 ? C1' C2' C4' C5' -172.3(2) 3_556 . . . ? C3' C2' C4' C5' -52.5(3) . . . . ? C1' C2' C4' C5' 65.3(3) . . . . ? C1' C2' C4' C9' 4.2(3) 3_556 . . . ? C3' C2' C4' C9' 124.0(2) . . . . ? C1' C2' C4' C9' -118.2(3) . . . . ? C9' C4' C5' C6' -1.6(4) . . . . ? C2' C4' C5' C6' 175.1(2) . . . . ? C4' C5' C6' C7' -1.1(4) . . . . ? C5' C6' C7' C8' 3.0(4) . . . . ? C5' C6' C7' C10' -177.8(3) . . . . ? C6' C7' C8' C9' -2.3(4) . . . . ? C10' C7' C8' C9' 178.5(3) . . . . ? C7' C8' C9' C4' -0.4(4) . . . . ? C5' C4' C9' C8' 2.3(4) . . . . ? C2' C4' C9' C8' -174.3(3) . . . . ? C6' C7' C10' N11' -157.0(3) . . . . ? C8' C7' C10' N11' 22.1(4) . . . . ? C6' C7' C10' C14' 20.2(5) . . . . ? C8' C7' C10' C14' -160.6(3) . . . . ? C14' C10' N11' N12' -1.2(4) . . . . ? C7' C10' N11' N12' 176.5(3) . . . . ? C10' N11' N12' N13' 1.0(3) . . . . ? N11' N12' N13' C14' -0.5(4) . . . . ? N11' N12' N13' C15' -176.5(3) . . . . ? N12' N13' C14' C10' -0.3(3) . . . . ? C15' N13' C14' C10' 175.5(3) . . . . ? N11' C10' C14' N13' 0.9(3) . . . . ? C7' C10' C14' N13' -176.7(3) . . . . ? C14' N13' C15' C16' -178.1(4) . . . . ? N12' N13' C15' C16' -2.8(5) . . . . ? C14' N13' C15' C20' -0.8(5) . . . . ? N12' N13' C15' C20' 174.6(3) . . . . ? C20' C15' C16' C17' -1.4(6) . . . . ? N13' C15' C16' C17' 175.9(4) . . . . ? C15' C16' C17' C18' 0.9(7) . . . . ? C16' C17' C18' C19' 0.1(7) . . . . ? C17' C18' C19' C20' -0.6(6) . . . . ? C16' C15' C20' C19' 0.9(5) . . . . ? N13' C15' C20' C19' -176.4(3) . . . . ? C18' C19' C20' C15' 0.1(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1C H1C N11 1.00 2.21 3.205(4) 174.7 . C1C H1C N12 1.00 2.58 3.512(4) 154.6 . C2C H2C N11' 1.00 2.32 3.312(5) 169.1 . C2C H2C N12' 1.00 2.77 3.725(5) 160.8 . C16 H16 Cl1 0.95 2.76 3.505(4) 136.1 1_554 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.909 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.077 #============================================================================== data_sb091_hy_compound_7 _database_code_depnum_ccdc_archive 'CCDC 734785' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Tetrakis(4-azidophenyl)methane ; _chemical_name_common Tetrakis(4-azidophenyl)methane _chemical_melting_point ? _chemical_formula_moiety 'C25 H16 N12' _chemical_formula_sum 'C25 H16 N12' _chemical_formula_weight 484.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.728(1) _cell_length_b 7.137(1) _cell_length_c 18.265(1) _cell_angle_alpha 90.00 _cell_angle_beta 111.37(1) _cell_angle_gamma 90.00 _cell_volume 2273.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 62 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description rods _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 60 sec./deg., 2 deg., 3 sets, 134 frames ; _diffrn_ambient_temperature 123(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-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8191 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2578 _reflns_number_gt 1710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0482P)^2^+1.3862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2578 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0935 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 C1 C 0.5000 0.4620(3) 0.2500 0.0169(5) Uani 1 2 d S . . C11 C 0.43869(11) 0.3324(2) 0.19220(10) 0.0184(4) Uani 1 1 d . . . C12 C 0.36075(11) 0.3430(2) 0.17843(11) 0.0209(4) Uani 1 1 d . . . H12 H 0.3429 0.4349 0.2053 0.025 Uiso 1 1 calc R . . C13 C 0.30808(11) 0.2216(2) 0.12605(11) 0.0218(4) Uani 1 1 d . . . H13 H 0.2550 0.2313 0.1174 0.026 Uiso 1 1 calc R . . C14 C 0.33384(11) 0.0866(2) 0.08672(11) 0.0203(4) Uani 1 1 d . . . C15 C 0.41151(11) 0.0720(2) 0.10059(11) 0.0219(4) Uani 1 1 d . . . H15 H 0.4295 -0.0207 0.0742 0.026 Uiso 1 1 calc R . . C16 C 0.46262(11) 0.1928(2) 0.15302(11) 0.0209(4) Uani 1 1 d . . . H16 H 0.5158 0.1803 0.1626 0.025 Uiso 1 1 calc R . . N11 N 0.28518(9) -0.0456(2) 0.03277(10) 0.0265(4) Uani 1 1 d . . . N12 N 0.21563(10) -0.0327(2) 0.02104(10) 0.0251(4) Uani 1 1 d . . . N13 N 0.15144(11) -0.0360(2) 0.00541(11) 0.0366(5) Uani 1 1 d . . . C21 C 0.53677(10) 0.5945(2) 0.20621(11) 0.0180(4) Uani 1 1 d . . . C22 C 0.52105(11) 0.5879(3) 0.12594(11) 0.0220(4) Uani 1 1 d . . . H22 H 0.4885 0.4922 0.0952 0.026 Uiso 1 1 calc R . . C23 C 0.55213(11) 0.7189(3) 0.08967(12) 0.0248(4) Uani 1 1 d . . . H23 H 0.5402 0.7133 0.0345 0.030 Uiso 1 1 calc R . . C24 C 0.60021(11) 0.8570(2) 0.13376(12) 0.0230(4) Uani 1 1 d . . . C25 C 0.61804(11) 0.8642(2) 0.21427(11) 0.0214(4) Uani 1 1 d . . . H25 H 0.6521 0.9572 0.2451 0.026 Uiso 1 1 calc R . . C26 C 0.58588(11) 0.7352(2) 0.24925(11) 0.0204(4) Uani 1 1 d . . . H26 H 0.5975 0.7424 0.3043 0.025 Uiso 1 1 calc R . . N21 N 0.62729(11) 0.9898(2) 0.09128(11) 0.0333(4) Uani 1 1 d . . . N22 N 0.67104(11) 1.1132(3) 0.13145(11) 0.0350(5) Uani 1 1 d . . . N23 N 0.71085(13) 1.2327(3) 0.16039(13) 0.0548(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0181(14) 0.0158(12) 0.0149(14) 0.000 0.0037(11) 0.000 C11 0.0214(10) 0.0151(9) 0.0168(10) 0.0030(7) 0.0047(8) 0.0006(7) C12 0.0250(11) 0.0160(9) 0.0220(11) 0.0003(7) 0.0091(9) 0.0021(7) C13 0.0174(10) 0.0222(9) 0.0238(11) 0.0027(8) 0.0051(8) 0.0011(7) C14 0.0233(11) 0.0169(9) 0.0172(10) 0.0019(7) 0.0034(8) -0.0015(7) C15 0.0263(11) 0.0174(9) 0.0214(11) -0.0003(7) 0.0080(9) 0.0021(7) C16 0.0190(10) 0.0189(9) 0.0229(11) 0.0017(7) 0.0054(8) 0.0020(7) N11 0.0220(10) 0.0261(9) 0.0294(10) -0.0055(7) 0.0071(8) -0.0055(7) N12 0.0279(11) 0.0227(8) 0.0217(9) -0.0023(7) 0.0054(8) -0.0046(7) N13 0.0240(11) 0.0420(11) 0.0385(12) -0.0058(8) 0.0051(9) -0.0049(8) C21 0.0170(10) 0.0171(9) 0.0189(10) 0.0015(7) 0.0054(8) 0.0032(7) C22 0.0221(11) 0.0224(9) 0.0203(11) -0.0030(8) 0.0064(8) -0.0001(8) C23 0.0276(11) 0.0296(10) 0.0187(10) -0.0011(8) 0.0104(9) 0.0017(8) C24 0.0223(11) 0.0228(10) 0.0266(12) 0.0049(8) 0.0121(9) 0.0030(8) C25 0.0203(10) 0.0195(9) 0.0223(11) -0.0010(7) 0.0054(8) -0.0006(7) C26 0.0219(10) 0.0195(9) 0.0180(10) 0.0003(7) 0.0051(8) 0.0021(7) N21 0.0371(11) 0.0368(10) 0.0294(11) -0.0011(8) 0.0159(9) -0.0131(8) N22 0.0311(11) 0.0400(11) 0.0337(11) 0.0134(9) 0.0115(9) -0.0030(9) N23 0.0531(14) 0.0527(13) 0.0465(14) 0.0123(10) 0.0040(11) -0.0281(11) _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 C1 C11 1.551(2) . ? C1 C11 1.551(2) 2_655 ? C1 C21 1.552(2) . ? C1 C21 1.552(2) 2_655 ? C11 C12 1.390(2) . ? C11 C16 1.393(2) . ? C12 C13 1.397(3) . ? C12 H12 0.9500 . ? C13 C14 1.389(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C14 N11 1.428(2) . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N11 N12 1.244(2) . ? N12 N13 1.130(2) . ? C21 C22 1.387(3) . ? C21 C26 1.395(3) . ? C22 C23 1.390(3) . ? C22 H22 0.9500 . ? C23 C24 1.379(3) . ? C23 H23 0.9500 . ? C24 C25 1.385(3) . ? C24 N21 1.430(2) . ? C25 C26 1.378(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N21 N22 1.244(2) . ? N22 N23 1.130(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 C11 C1 C11 106.76(19) . 2_655 ? C11 C1 C21 111.71(9) . . ? C11 C1 C21 110.89(9) 2_655 . ? C11 C1 C21 110.89(9) . 2_655 ? C11 C1 C21 111.71(9) 2_655 2_655 ? C21 C1 C21 104.96(19) . 2_655 ? C12 C11 C16 117.33(16) . . ? C12 C11 C1 123.99(15) . . ? C16 C11 C1 118.66(15) . . ? C11 C12 C13 121.56(17) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 119.51(17) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 119.79(17) . . ? C15 C14 N11 116.08(16) . . ? C13 C14 N11 124.11(17) . . ? C16 C15 C14 119.69(17) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C11 122.10(17) . . ? C15 C16 H16 118.9 . . ? C11 C16 H16 118.9 . . ? N12 N11 C14 115.76(16) . . ? N13 N12 N11 173.01(19) . . ? C22 C21 C26 117.55(17) . . ? C22 C21 C1 124.12(15) . . ? C26 C21 C1 118.26(15) . . ? C21 C22 C23 121.09(18) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 119.99(19) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.01(17) . . ? C23 C24 N21 116.23(18) . . ? C25 C24 N21 123.74(17) . . ? C26 C25 C24 119.36(17) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C21 121.98(18) . . ? C25 C26 H26 119.0 . . ? C21 C26 H26 119.0 . . ? N22 N21 C24 115.90(17) . . ? N23 N22 N21 172.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C11 C12 125.63(19) 2_655 . . . ? C21 C1 C11 C12 -112.98(17) . . . . ? C21 C1 C11 C12 3.7(2) 2_655 . . . ? C11 C1 C11 C16 -52.43(13) 2_655 . . . ? C21 C1 C11 C16 69.0(2) . . . . ? C21 C1 C11 C16 -174.34(15) 2_655 . . . ? C16 C11 C12 C13 -1.5(3) . . . . ? C1 C11 C12 C13 -179.54(16) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C12 C13 C14 C15 0.9(3) . . . . ? C12 C13 C14 N11 179.22(17) . . . . ? C13 C14 C15 C16 -0.5(3) . . . . ? N11 C14 C15 C16 -178.96(16) . . . . ? C14 C15 C16 C11 -0.9(3) . . . . ? C12 C11 C16 C15 1.9(3) . . . . ? C1 C11 C16 C15 -179.94(16) . . . . ? C15 C14 N11 N12 179.46(17) . . . . ? C13 C14 N11 N12 1.1(3) . . . . ? C14 N11 N12 N13 -179(100) . . . . ? C11 C1 C21 C22 -4.6(2) . . . . ? C11 C1 C21 C22 114.32(17) 2_655 . . . ? C21 C1 C21 C22 -124.89(19) 2_655 . . . ? C11 C1 C21 C26 172.07(15) . . . . ? C11 C1 C21 C26 -69.0(2) 2_655 . . . ? C21 C1 C21 C26 51.83(13) 2_655 . . . ? C26 C21 C22 C23 -1.1(3) . . . . ? C1 C21 C22 C23 175.64(16) . . . . ? C21 C22 C23 C24 0.8(3) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C22 C23 C24 N21 -177.78(17) . . . . ? C23 C24 C25 C26 -1.5(3) . . . . ? N21 C24 C25 C26 176.65(18) . . . . ? C24 C25 C26 C21 1.2(3) . . . . ? C22 C21 C26 C25 0.1(3) . . . . ? C1 C21 C26 C25 -176.87(16) . . . . ? C23 C24 N21 N22 -179.52(18) . . . . ? C25 C24 N21 N22 2.2(3) . . . . ? C24 N21 N22 N23 -179(100) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C22 H22 N13 0.95 2.61 3.268(3) 126.3 7 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.287 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.052 #============================================================================== #_eof # End of Crystallographic Information File