# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 _publ_contact_author_name 'Prof Martin R Bryce' _publ_contact_author_address ; Department of Chemistry University of Durham Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email M.R.BRYCE@DURHAM.AC.UK loop_ _publ_author_name 'Kreher, David' 'Batsanov, Andrei S.' 'Wang, Changsheng' 'Bryce, Martin R.' _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; 2,5-Diphenyl-1,3,4-oxadiazoles bearing a terminal ethynyl or butadiynyl substituent: functionalisation reactions and X-ray crystal structures of the products ; #====================================================================== data_(3) _database_code_depnum_ccdc_archive 'CCDC 225628' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(4-tert-Butylphenyl)-5-[4-(3,3-diethoxy-propyn-1-yl)- phenyl]-1,3,4-oxadiazole ; _chemical_name_common ? _chemical_melting_point '82--84\% C' _chemical_formula_moiety 'C25 H28 N2 O3' _chemical_formula_sum 'C25 H28 N2 O3' _chemical_formula_weight 404.49 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 P2(1)/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 7.356(2) _cell_length_b 19.870(5) _cell_length_c 15.136(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.37(1) _cell_angle_gamma 90.00 _cell_volume 2211.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 972 _cell_measurement_theta_min 10.25 _cell_measurement_theta_max 24.27 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9103 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 -1.00 0.0700 0.00 -1.00 1.00 0.0700 0.00 1.00 1.00 0.0350 0.00 -1.00 -1.00 0.0350 -2.00 -1.00 0.00 0.2750 2.00 1.00 0.00 0.2750 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.42 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 24719 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.56 _reflns_number_total 5123 _reflns_number_gt 3761 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.060 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.060 (Bruker, 1999)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 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. ; _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^)+(0.0477P)^2^+0.3990P] 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_number_reflns 5123 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 O1 O 0.20939(12) 0.44763(5) 0.48344(6) 0.0222(2) Uani 1 1 d . . . O2 O 0.61808(13) 0.63098(5) 1.06663(6) 0.0274(2) Uani 1 1 d . . . O3 O 0.87986(13) 0.58319(5) 1.00869(6) 0.0252(2) Uani 1 1 d . . . N1 N 0.15858(16) 0.52181(6) 0.37671(7) 0.0278(3) Uani 1 1 d . . . N2 N 0.23110(16) 0.55582(6) 0.45103(7) 0.0275(3) Uani 1 1 d . . . C1 C 0.14865(17) 0.45923(7) 0.39841(8) 0.0217(3) Uani 1 1 d . . . C2 C 0.25856(17) 0.51061(7) 0.51132(9) 0.0217(3) Uani 1 1 d . . . C3 C -0.1016(2) 0.23711(7) 0.17794(9) 0.0280(3) Uani 1 1 d . . . C4 C -0.2660(3) 0.20102(10) 0.21613(12) 0.0425(4) Uani 1 1 d . . . H41 H -0.242(3) 0.1859(10) 0.2758(13) 0.053(5) Uiso 1 1 d . . . H42 H -0.301(2) 0.1614(9) 0.1788(11) 0.044(5) Uiso 1 1 d . . . H43 H -0.371(3) 0.2323(10) 0.2169(12) 0.052(6) Uiso 1 1 d . . . C5 C -0.1540(2) 0.25897(9) 0.08379(10) 0.0345(4) Uani 1 1 d . . . H51 H -0.197(2) 0.2185(9) 0.0500(10) 0.035(4) Uiso 1 1 d . . . H52 H -0.046(2) 0.2786(9) 0.0515(11) 0.041(5) Uiso 1 1 d . . . H53 H -0.261(2) 0.2930(9) 0.0856(11) 0.043(5) Uiso 1 1 d . . . C6 C 0.0589(3) 0.18792(9) 0.17307(13) 0.0421(4) Uani 1 1 d . . . H61 H 0.026(3) 0.1501(10) 0.1363(13) 0.056(6) Uiso 1 1 d . . . H62 H 0.096(2) 0.1720(9) 0.2328(12) 0.048(5) Uiso 1 1 d . . . H63 H 0.170(3) 0.2102(9) 0.1456(11) 0.048(5) Uiso 1 1 d . . . C7 C 0.54185(18) 0.55813(7) 0.85828(9) 0.0243(3) Uani 1 1 d . . . C8 C 0.60798(19) 0.56928(7) 0.92955(9) 0.0247(3) Uani 1 1 d . . . C9 C 0.69110(19) 0.57698(7) 1.01887(9) 0.0243(3) Uani 1 1 d . . . H9 H 0.6620(19) 0.5369(7) 1.0559(9) 0.021(4) Uiso 1 1 d . . . C11 C 0.08265(17) 0.40297(7) 0.34487(8) 0.0213(3) Uani 1 1 d . . . C12 C 0.05626(19) 0.41234(8) 0.25432(9) 0.0256(3) Uani 1 1 d . . . H12 H 0.081(2) 0.4541(9) 0.2279(10) 0.035(4) Uiso 1 1 d . . . C13 C -0.00579(19) 0.35994(7) 0.20115(9) 0.0260(3) Uani 1 1 d . . . H13 H -0.020(2) 0.3692(8) 0.1403(10) 0.029(4) Uiso 1 1 d . . . C14 C -0.04280(18) 0.29693(7) 0.23590(9) 0.0235(3) Uani 1 1 d . . . C15 C -0.0165(2) 0.28843(7) 0.32726(9) 0.0271(3) Uani 1 1 d . . . H15 H -0.038(2) 0.2459(8) 0.3556(10) 0.032(4) Uiso 1 1 d . . . C16 C 0.04546(19) 0.34045(7) 0.38109(9) 0.0251(3) Uani 1 1 d . . . H16 H 0.059(2) 0.3329(8) 0.4446(11) 0.040(4) Uiso 1 1 d . . . C17 C 0.6443(2) 0.69521(8) 1.02619(11) 0.0324(3) Uani 1 1 d . . . H171 H 0.592(2) 0.6937(8) 0.9678(11) 0.034(4) Uiso 1 1 d . . . H172 H 0.778(2) 0.7054(8) 1.0223(10) 0.033(4) Uiso 1 1 d . . . C18 C 0.5534(2) 0.74724(10) 1.08194(14) 0.0440(4) Uani 1 1 d . . . H181 H 0.419(3) 0.7392(9) 1.0842(11) 0.045(5) Uiso 1 1 d . . . H182 H 0.606(3) 0.7477(10) 1.1423(14) 0.064(6) Uiso 1 1 d . . . H183 H 0.569(3) 0.7927(11) 1.0526(12) 0.059(6) Uiso 1 1 d . . . C19 C 0.9813(2) 0.56820(9) 1.08881(10) 0.0329(4) Uani 1 1 d . . . H191 H 0.970(2) 0.5175(10) 1.0993(11) 0.047(5) Uiso 1 1 d . . . H192 H 0.924(2) 0.5925(9) 1.1377(11) 0.041(5) Uiso 1 1 d . . . C20 C 1.1745(2) 0.58856(9) 1.07597(13) 0.0394(4) Uani 1 1 d . . . H201 H 1.250(3) 0.5758(9) 1.1299(12) 0.049(5) Uiso 1 1 d . . . H202 H 1.179(2) 0.6384(10) 1.0670(11) 0.051(5) Uiso 1 1 d . . . H203 H 1.222(3) 0.5657(10) 1.0246(13) 0.054(5) Uiso 1 1 d . . . C21 C 0.33174(17) 0.52057(7) 0.60067(8) 0.0210(3) Uani 1 1 d . . . C22 C 0.37934(19) 0.58569(7) 0.62652(9) 0.0245(3) Uani 1 1 d . . . H22 H 0.364(2) 0.6204(8) 0.5845(10) 0.031(4) Uiso 1 1 d . . . C23 C 0.44685(19) 0.59775(7) 0.71073(9) 0.0254(3) Uani 1 1 d . . . H23 H 0.479(2) 0.6434(8) 0.7281(10) 0.030(4) Uiso 1 1 d . . . C24 C 0.46843(17) 0.54492(7) 0.77088(8) 0.0226(3) Uani 1 1 d . . . C25 C 0.42095(19) 0.47972(7) 0.74483(9) 0.0249(3) Uani 1 1 d . . . H25 H 0.434(2) 0.4427(8) 0.7854(10) 0.032(4) Uiso 1 1 d . . . C26 C 0.35336(19) 0.46769(7) 0.66022(9) 0.0241(3) Uani 1 1 d . . . H26 H 0.320(2) 0.4228(8) 0.6428(9) 0.027(4) 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 O1 0.0249(5) 0.0231(5) 0.0185(4) -0.0003(4) -0.0017(4) -0.0021(4) O2 0.0291(5) 0.0287(6) 0.0245(5) -0.0064(4) 0.0047(4) -0.0032(4) O3 0.0257(5) 0.0281(5) 0.0218(5) 0.0003(4) -0.0016(4) 0.0003(4) N1 0.0343(7) 0.0243(7) 0.0245(6) 0.0003(5) -0.0048(5) -0.0025(5) N2 0.0340(7) 0.0240(6) 0.0244(6) -0.0003(5) -0.0045(5) -0.0010(5) C1 0.0198(7) 0.0263(8) 0.0188(6) 0.0019(5) 0.0002(5) 0.0008(5) C2 0.0204(7) 0.0198(7) 0.0249(7) -0.0018(5) 0.0009(5) -0.0009(5) C3 0.0329(8) 0.0262(8) 0.0248(7) -0.0051(6) -0.0006(6) 0.0001(6) C4 0.0511(12) 0.0408(11) 0.0357(10) -0.0094(8) 0.0050(8) -0.0166(9) C5 0.0394(9) 0.0384(10) 0.0254(8) -0.0078(7) -0.0035(7) -0.0032(8) C6 0.0468(11) 0.0329(10) 0.0460(10) -0.0119(8) -0.0070(8) 0.0088(8) C7 0.0240(7) 0.0240(7) 0.0251(7) -0.0014(6) 0.0024(5) -0.0033(5) C8 0.0259(7) 0.0228(7) 0.0253(7) -0.0017(6) 0.0029(6) -0.0038(5) C9 0.0278(7) 0.0243(7) 0.0209(7) -0.0013(6) 0.0015(5) -0.0053(6) C11 0.0186(7) 0.0246(7) 0.0206(6) -0.0003(5) -0.0004(5) 0.0007(5) C12 0.0286(8) 0.0255(8) 0.0225(7) 0.0054(6) 0.0001(6) -0.0036(6) C13 0.0286(8) 0.0316(8) 0.0177(7) 0.0017(6) -0.0008(5) -0.0020(6) C14 0.0227(7) 0.0257(8) 0.0221(7) -0.0010(5) 0.0001(5) 0.0013(5) C15 0.0331(8) 0.0224(8) 0.0256(7) 0.0040(6) -0.0020(6) -0.0004(6) C16 0.0301(8) 0.0259(8) 0.0191(7) 0.0028(6) -0.0015(5) 0.0015(6) C17 0.0318(9) 0.0267(8) 0.0388(9) -0.0040(7) 0.0033(7) -0.0010(6) C18 0.0323(10) 0.0386(11) 0.0612(12) -0.0187(9) 0.0034(8) 0.0020(8) C19 0.0383(9) 0.0351(9) 0.0248(8) 0.0001(7) -0.0088(6) 0.0022(7) C20 0.0347(9) 0.0348(10) 0.0479(10) -0.0060(8) -0.0125(8) 0.0054(7) C21 0.0177(6) 0.0240(7) 0.0213(6) -0.0012(5) 0.0011(5) -0.0008(5) C22 0.0254(7) 0.0233(8) 0.0246(7) 0.0033(6) 0.0002(5) -0.0015(6) C23 0.0251(7) 0.0218(7) 0.0293(7) -0.0029(6) -0.0002(6) -0.0034(6) C24 0.0194(7) 0.0266(7) 0.0217(7) -0.0032(5) 0.0014(5) -0.0015(5) C25 0.0292(8) 0.0222(7) 0.0232(7) 0.0015(6) -0.0004(6) -0.0011(6) C26 0.0283(7) 0.0198(7) 0.0241(7) -0.0028(6) -0.0001(5) -0.0021(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 O1 C2 1.3667(16) . ? O1 C1 1.3718(15) . ? O2 C9 1.4076(17) . ? O2 C17 1.4305(19) . ? O3 C9 1.4061(17) . ? O3 C19 1.4395(17) . ? N1 C1 1.2886(18) . ? N1 N2 1.4063(16) . ? N2 C2 1.2928(17) . ? C1 C11 1.4573(18) . ? C2 C21 1.4572(18) . ? C3 C5 1.530(2) . ? C3 C4 1.531(2) . ? C3 C14 1.5333(19) . ? C3 C6 1.536(2) . ? C4 H41 0.964(19) . ? C4 H42 1.000(18) . ? C4 H43 0.99(2) . ? C5 H51 1.000(17) . ? C5 H52 1.021(18) . ? C5 H53 1.038(18) . ? C6 H61 0.96(2) . ? C6 H62 0.991(18) . ? C6 H63 1.027(19) . ? C7 C8 1.1934(19) . ? C7 C24 1.4409(18) . ? C8 C9 1.4783(19) . ? C9 H9 1.000(15) . ? C11 C16 1.388(2) . ? C11 C12 1.3922(18) . ? C12 C13 1.387(2) . ? C12 H12 0.940(17) . ? C13 C14 1.388(2) . ? C13 H13 0.942(15) . ? C14 C15 1.4019(19) . ? C15 C16 1.387(2) . ? C15 H15 0.962(16) . ? C16 H16 0.976(16) . ? C17 C18 1.502(2) . ? C17 H171 0.955(16) . ? C17 H172 1.009(16) . ? C18 H181 1.000(19) . ? C18 H182 0.98(2) . ? C18 H183 1.01(2) . ? C19 C20 1.495(2) . ? C19 H191 1.023(19) . ? C19 H192 0.986(18) . ? C20 H201 1.008(19) . ? C20 H202 1.00(2) . ? C20 H203 0.97(2) . ? C21 C26 1.3910(19) . ? C21 C22 1.3940(19) . ? C22 C23 1.378(2) . ? C22 H22 0.943(16) . ? C23 C24 1.3962(19) . ? C23 H23 0.972(16) . ? C24 C25 1.3962(19) . ? C25 C26 1.3833(19) . ? C25 H25 0.962(16) . ? C26 H26 0.960(16) . ? 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 O1 C1 102.33(10) . . ? C9 O2 C17 113.79(11) . . ? C9 O3 C19 112.50(11) . . ? C1 N1 N2 106.41(11) . . ? C2 N2 N1 106.30(11) . . ? N1 C1 O1 112.47(11) . . ? N1 C1 C11 128.22(12) . . ? O1 C1 C11 119.31(11) . . ? N2 C2 O1 112.49(11) . . ? N2 C2 C21 127.50(12) . . ? O1 C2 C21 120.00(11) . . ? C5 C3 C4 107.50(13) . . ? C5 C3 C14 111.97(12) . . ? C4 C3 C14 111.20(12) . . ? C5 C3 C6 108.24(13) . . ? C4 C3 C6 109.57(15) . . ? C14 C3 C6 108.31(12) . . ? C3 C4 H41 111.8(11) . . ? C3 C4 H42 110.6(10) . . ? H41 C4 H42 108.8(15) . . ? C3 C4 H43 109.4(11) . . ? H41 C4 H43 108.1(15) . . ? H42 C4 H43 108.0(14) . . ? C3 C5 H51 108.6(9) . . ? C3 C5 H52 111.9(9) . . ? H51 C5 H52 107.6(13) . . ? C3 C5 H53 109.5(9) . . ? H51 C5 H53 107.9(13) . . ? H52 C5 H53 111.3(14) . . ? C3 C6 H61 110.1(11) . . ? C3 C6 H62 111.0(10) . . ? H61 C6 H62 109.8(16) . . ? C3 C6 H63 111.5(10) . . ? H61 C6 H63 106.9(15) . . ? H62 C6 H63 107.4(14) . . ? C8 C7 C24 177.92(15) . . ? C7 C8 C9 175.24(15) . . ? O3 C9 O2 112.29(11) . . ? O3 C9 C8 107.27(11) . . ? O2 C9 C8 113.20(12) . . ? O3 C9 H9 110.9(8) . . ? O2 C9 H9 103.2(8) . . ? C8 C9 H9 110.0(8) . . ? C16 C11 C12 118.98(13) . . ? C16 C11 C1 122.22(12) . . ? C12 C11 C1 118.79(12) . . ? C13 C12 C11 120.47(13) . . ? C13 C12 H12 118.7(9) . . ? C11 C12 H12 120.8(9) . . ? C12 C13 C14 121.50(13) . . ? C12 C13 H13 116.6(9) . . ? C14 C13 H13 121.9(9) . . ? C13 C14 C15 117.32(13) . . ? C13 C14 C3 122.53(12) . . ? C15 C14 C3 120.08(13) . . ? C16 C15 C14 121.70(13) . . ? C16 C15 H15 116.6(9) . . ? C14 C15 H15 121.6(9) . . ? C15 C16 C11 120.03(13) . . ? C15 C16 H16 119.3(10) . . ? C11 C16 H16 120.7(10) . . ? O2 C17 C18 107.90(14) . . ? O2 C17 H171 108.2(10) . . ? C18 C17 H171 111.6(10) . . ? O2 C17 H172 110.2(9) . . ? C18 C17 H172 110.1(9) . . ? H171 C17 H172 108.8(13) . . ? C17 C18 H181 111.2(10) . . ? C17 C18 H182 110.9(12) . . ? H181 C18 H182 109.7(15) . . ? C17 C18 H183 108.2(11) . . ? H181 C18 H183 106.1(15) . . ? H182 C18 H183 110.6(17) . . ? O3 C19 C20 108.03(13) . . ? O3 C19 H191 106.9(10) . . ? C20 C19 H191 111.7(10) . . ? O3 C19 H192 108.1(10) . . ? C20 C19 H192 112.9(10) . . ? H191 C19 H192 109.0(14) . . ? C19 C20 H201 109.4(11) . . ? C19 C20 H202 108.7(11) . . ? H201 C20 H202 109.8(14) . . ? C19 C20 H203 109.6(11) . . ? H201 C20 H203 109.4(15) . . ? H202 C20 H203 109.9(15) . . ? C26 C21 C22 119.68(12) . . ? C26 C21 C2 122.20(12) . . ? C22 C21 C2 118.12(12) . . ? C23 C22 C21 120.25(13) . . ? C23 C22 H22 122.1(10) . . ? C21 C22 H22 117.6(9) . . ? C22 C23 C24 120.35(13) . . ? C22 C23 H23 119.6(9) . . ? C24 C23 H23 120.1(9) . . ? C23 C24 C25 119.32(12) . . ? C23 C24 C7 119.74(12) . . ? C25 C24 C7 120.93(12) . . ? C26 C25 C24 120.25(13) . . ? C26 C25 H25 119.2(9) . . ? C24 C25 H25 120.5(9) . . ? C25 C26 C21 120.15(13) . . ? C25 C26 H26 119.9(9) . . ? C21 C26 H26 120.0(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.222 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.042 #============================================END data_(4) _database_code_depnum_ccdc_archive 'CCDC 225629' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(4-tert-Butylphenyl)-5-[4-(5,5-diethoxy-1,3-pentadiyn-1-yl)- phenyl]-1,3,4-oxadiazole ; _chemical_name_common ? _chemical_melting_point '141--143\% C' _chemical_formula_moiety 'C27 H28 N2 O3' _chemical_formula_sum 'C27 H28 N2 O3' _chemical_formula_weight 428.51 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 P2(1)/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 14.835(5) _cell_length_b 6.161(1) _cell_length_c 25.549(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.14(1) _cell_angle_gamma 90.00 _cell_volume 2334.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 759 _cell_measurement_theta_min 12.07 _cell_measurement_theta_max 22.46 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.0250 -1.00 0.00 0.00 0.0250 0.00 1.00 0.00 0.2800 0.00 -1.00 0.00 0.2800 0.00 0.00 1.00 0.1200 -1.00 0.00 -3.00 0.1100 _exptl_special_details ;The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (15 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.42 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19697 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 29.06 _reflns_number_total 6234 _reflns_number_gt 4459 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.060 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.060 (Bruker, 1999)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 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. ; _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^)+(0.0740P)^2^+0.6572P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6234 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1520 _refine_ls_wR_factor_gt 0.1371 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.39789(7) 0.52895(18) 0.21761(4) 0.0209(2) Uani 1 1 d . . . O2 O 0.81485(8) 0.14954(19) -0.18377(4) 0.0269(3) Uani 1 1 d . . . O3 O 0.83892(7) -0.15732(19) -0.13629(5) 0.0282(3) Uani 1 1 d . . . N1 N 0.40465(9) 0.8612(2) 0.25052(5) 0.0248(3) Uani 1 1 d . . . N2 N 0.45463(9) 0.8566(2) 0.20420(5) 0.0249(3) Uani 1 1 d . . . C1 C 0.37374(10) 0.6662(3) 0.25674(6) 0.0204(3) Uani 1 1 d . . . C2 C 0.44905(10) 0.6593(3) 0.18681(6) 0.0198(3) Uani 1 1 d . . . C3 C 0.13510(10) 0.3885(3) 0.42101(6) 0.0242(3) Uani 1 1 d . . . C4 C 0.13030(14) 0.1434(3) 0.42945(8) 0.0349(4) Uani 1 1 d . . . H41 H 0.1105(14) 0.064(4) 0.3960(8) 0.041(6) Uiso 1 1 d . . . H42 H 0.0845(14) 0.109(3) 0.4575(8) 0.039(6) Uiso 1 1 d . . . H43 H 0.1883(16) 0.087(4) 0.4437(9) 0.056(7) Uiso 1 1 d . . . C5 C 0.15812(18) 0.4921(4) 0.47421(8) 0.0475(6) Uani 1 1 d . . . H51 H 0.1121(14) 0.434(4) 0.5001(8) 0.043(6) Uiso 1 1 d . . . H52 H 0.1516(18) 0.657(5) 0.4733(10) 0.068(8) Uiso 1 1 d . . . H53 H 0.2243(18) 0.441(4) 0.4868(10) 0.068(8) Uiso 1 1 d . . . C6 C 0.04263(13) 0.4710(4) 0.40145(10) 0.0440(5) Uani 1 1 d . . . H61 H -0.0054(16) 0.433(4) 0.4258(9) 0.053(7) Uiso 1 1 d . . . H62 H 0.0281(15) 0.395(4) 0.3667(10) 0.055(7) Uiso 1 1 d . . . H63 H 0.0463(17) 0.635(5) 0.3979(10) 0.064(8) Uiso 1 1 d . . . C7 C 0.60826(10) 0.3161(3) 0.00451(6) 0.0240(3) Uani 1 1 d . . . C8 C 0.64285(10) 0.2426(3) -0.03367(6) 0.0244(3) Uani 1 1 d . . . C9 C 0.68323(10) 0.1560(3) -0.07693(6) 0.0241(3) Uani 1 1 d . . . C10 C 0.72051(10) 0.0832(3) -0.11437(6) 0.0247(3) Uani 1 1 d . . . C11 C 0.31797(10) 0.5859(3) 0.29883(6) 0.0203(3) Uani 1 1 d . . . C12 C 0.30108(11) 0.7218(3) 0.34115(6) 0.0237(3) Uani 1 1 d . . . H12 H 0.3298(13) 0.858(3) 0.3432(8) 0.034(5) Uiso 1 1 d . . . C13 C 0.24570(11) 0.6533(3) 0.38070(7) 0.0249(3) Uani 1 1 d . . . H13 H 0.2343(14) 0.753(4) 0.4087(8) 0.041(6) Uiso 1 1 d . . . C14 C 0.20422(10) 0.4503(3) 0.37983(6) 0.0211(3) Uani 1 1 d . . . C15 C 0.22422(12) 0.3137(3) 0.33800(7) 0.0289(4) Uani 1 1 d . . . H15 H 0.2011(13) 0.168(4) 0.3361(8) 0.036(5) Uiso 1 1 d . . . C16 C 0.28088(12) 0.3791(3) 0.29845(7) 0.0283(4) Uani 1 1 d . . . H16 H 0.2966(13) 0.281(4) 0.2717(8) 0.038(6) Uiso 1 1 d . . . C17 C 0.85393(13) 0.0778(3) -0.23177(7) 0.0330(4) Uani 1 1 d . . . H171 H 0.8052(13) 0.052(3) -0.2573(8) 0.034(5) Uiso 1 1 d . . . H172 H 0.8878(14) -0.052(4) -0.2251(8) 0.035(5) Uiso 1 1 d . . . C18 C 0.91496(15) 0.2539(4) -0.25069(9) 0.0443(5) Uani 1 1 d . . . H181 H 0.9651(17) 0.284(4) -0.2250(10) 0.060(7) Uiso 1 1 d . . . H182 H 0.8811(15) 0.388(4) -0.2526(8) 0.045(6) Uiso 1 1 d . . . H183 H 0.9398(16) 0.213(4) -0.2850(10) 0.060(7) Uiso 1 1 d . . . C19 C 0.80420(12) -0.3571(3) -0.11638(8) 0.0340(4) Uani 1 1 d . . . H191 H 0.7752(15) -0.439(4) -0.1477(9) 0.052(7) Uiso 1 1 d . . . H192 H 0.7581(14) -0.318(4) -0.0883(8) 0.042(6) Uiso 1 1 d . . . C20 C 0.88297(14) -0.4821(3) -0.09426(10) 0.0400(5) Uani 1 1 d . . . H201 H 0.9290(18) -0.506(4) -0.1238(10) 0.065(8) Uiso 1 1 d . . . H202 H 0.9144(16) -0.400(4) -0.0655(10) 0.058(7) Uiso 1 1 d . . . H203 H 0.8633(16) -0.628(4) -0.0799(10) 0.059(7) Uiso 1 1 d . . . C21 C 0.48917(10) 0.5687(3) 0.14011(6) 0.0203(3) Uani 1 1 d . . . C22 C 0.54959(10) 0.6955(3) 0.11199(6) 0.0221(3) Uani 1 1 d . . . H22 H 0.5656(13) 0.831(3) 0.1237(8) 0.033(5) Uiso 1 1 d . . . C23 C 0.58834(11) 0.6137(3) 0.06744(6) 0.0235(3) Uani 1 1 d . . . H23 H 0.6292(12) 0.700(3) 0.0479(7) 0.028(5) Uiso 1 1 d . . . C24 C 0.56710(10) 0.4035(3) 0.05013(6) 0.0223(3) Uani 1 1 d . . . C25 C 0.50588(11) 0.2777(3) 0.07820(6) 0.0236(3) Uani 1 1 d . . . H25 H 0.4902(12) 0.132(3) 0.0665(7) 0.025(5) Uiso 1 1 d . . . C26 C 0.46795(11) 0.3594(3) 0.12311(6) 0.0225(3) Uani 1 1 d . . . H26 H 0.4270(12) 0.270(3) 0.1413(7) 0.029(5) Uiso 1 1 d . . . C27 C 0.77150(11) -0.0166(3) -0.15717(6) 0.0245(3) Uani 1 1 d . . . H27 H 0.7306(12) -0.102(3) -0.1808(7) 0.023(4) 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 O1 0.0237(5) 0.0212(6) 0.0178(5) -0.0020(4) 0.0038(4) 0.0004(4) O2 0.0336(6) 0.0253(6) 0.0223(6) -0.0029(5) 0.0088(5) -0.0010(5) O3 0.0237(5) 0.0267(6) 0.0342(7) -0.0007(5) 0.0027(5) 0.0004(5) N1 0.0294(7) 0.0252(7) 0.0199(7) -0.0043(5) 0.0057(5) -0.0019(6) N2 0.0296(7) 0.0251(7) 0.0201(7) -0.0035(5) 0.0043(5) -0.0021(6) C1 0.0218(7) 0.0222(8) 0.0172(7) -0.0044(6) 0.0001(6) 0.0022(6) C2 0.0207(7) 0.0228(8) 0.0160(7) 0.0018(6) 0.0014(5) 0.0008(6) C3 0.0253(7) 0.0236(8) 0.0241(8) -0.0040(6) 0.0069(6) -0.0012(6) C4 0.0388(10) 0.0284(10) 0.0379(11) 0.0011(8) 0.0121(8) -0.0031(8) C5 0.0628(14) 0.0524(14) 0.0279(10) -0.0132(10) 0.0203(10) -0.0259(12) C6 0.0268(9) 0.0493(13) 0.0564(14) 0.0126(11) 0.0137(9) 0.0053(9) C7 0.0241(7) 0.0274(8) 0.0205(8) 0.0020(6) 0.0012(6) 0.0036(6) C8 0.0235(7) 0.0265(8) 0.0231(8) 0.0012(7) -0.0003(6) 0.0041(6) C9 0.0244(7) 0.0260(8) 0.0221(8) 0.0006(6) 0.0023(6) 0.0029(6) C10 0.0263(7) 0.0254(8) 0.0224(8) -0.0003(7) 0.0009(6) 0.0022(6) C11 0.0194(6) 0.0223(8) 0.0193(7) -0.0026(6) 0.0008(5) 0.0009(6) C12 0.0253(7) 0.0221(8) 0.0238(8) -0.0064(6) 0.0042(6) -0.0024(6) C13 0.0265(7) 0.0249(8) 0.0235(8) -0.0080(7) 0.0063(6) -0.0007(6) C14 0.0195(7) 0.0233(8) 0.0205(7) -0.0032(6) 0.0009(6) 0.0006(6) C15 0.0382(9) 0.0227(9) 0.0262(9) -0.0061(7) 0.0075(7) -0.0078(7) C16 0.0380(9) 0.0241(8) 0.0232(8) -0.0079(7) 0.0089(7) -0.0046(7) C17 0.0374(9) 0.0372(11) 0.0247(9) -0.0021(8) 0.0101(8) 0.0033(8) C18 0.0398(11) 0.0572(14) 0.0363(12) 0.0096(10) 0.0103(9) -0.0037(10) C19 0.0310(9) 0.0252(9) 0.0458(11) 0.0014(8) -0.0001(8) 0.0002(7) C20 0.0380(10) 0.0286(10) 0.0531(13) 0.0012(9) -0.0086(9) 0.0015(8) C21 0.0216(7) 0.0223(8) 0.0171(7) 0.0008(6) 0.0001(6) 0.0037(6) C22 0.0248(7) 0.0214(8) 0.0201(8) 0.0016(6) -0.0006(6) 0.0002(6) C23 0.0239(7) 0.0268(8) 0.0198(8) 0.0045(7) 0.0034(6) 0.0013(6) C24 0.0240(7) 0.0266(8) 0.0162(7) 0.0009(6) 0.0005(6) 0.0053(6) C25 0.0284(8) 0.0210(8) 0.0214(8) -0.0008(6) 0.0012(6) 0.0025(6) C26 0.0246(7) 0.0228(8) 0.0203(8) 0.0017(6) 0.0032(6) -0.0001(6) C27 0.0261(7) 0.0237(8) 0.0240(8) -0.0035(7) 0.0048(6) 0.0016(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3628(18) . ? O1 C2 1.3653(18) . ? O2 C27 1.393(2) . ? O2 C17 1.436(2) . ? O3 C27 1.420(2) . ? O3 C19 1.431(2) . ? N1 C1 1.297(2) . ? N1 N2 1.4093(19) . ? N2 C2 1.296(2) . ? C1 C11 1.457(2) . ? C2 C21 1.455(2) . ? C3 C4 1.527(3) . ? C3 C14 1.532(2) . ? C3 C5 1.534(3) . ? C3 C6 1.537(3) . ? C4 H41 1.02(2) . ? C4 H42 1.02(2) . ? C4 H43 0.99(2) . ? C5 H51 1.03(2) . ? C5 H52 1.02(3) . ? C5 H53 1.07(3) . ? C6 H61 0.98(2) . ? C6 H62 1.02(3) . ? C6 H63 1.02(3) . ? C7 C8 1.200(2) . ? C7 C24 1.432(2) . ? C8 C9 1.375(2) . ? C9 C10 1.201(2) . ? C10 C27 1.476(2) . ? C11 C16 1.388(2) . ? C11 C12 1.394(2) . ? C12 C13 1.381(2) . ? C12 H12 0.94(2) . ? C13 C14 1.394(2) . ? C13 H13 0.96(2) . ? C14 C15 1.397(2) . ? C15 C16 1.387(2) . ? C15 H15 0.96(2) . ? C16 H16 0.95(2) . ? C17 C18 1.499(3) . ? C17 H171 0.98(2) . ? C17 H172 0.96(2) . ? C18 H181 1.00(3) . ? C18 H182 0.97(2) . ? C18 H183 0.99(3) . ? C19 C20 1.500(3) . ? C19 H191 1.03(2) . ? C19 H192 1.03(2) . ? C20 H201 1.04(3) . ? C20 H202 1.00(3) . ? C20 H203 1.01(3) . ? C21 C26 1.395(2) . ? C21 C22 1.398(2) . ? C22 C23 1.380(2) . ? C22 H22 0.92(2) . ? C23 C24 1.402(2) . ? C23 H23 0.956(19) . ? C24 C25 1.402(2) . ? C25 C26 1.383(2) . ? C25 H25 0.971(19) . ? C26 H26 0.95(2) . ? C27 H27 0.999(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 102.41(12) . . ? C27 O2 C17 112.87(13) . . ? C27 O3 C19 113.75(12) . . ? C1 N1 N2 106.12(12) . . ? C2 N2 N1 105.99(13) . . ? N1 C1 O1 112.73(13) . . ? N1 C1 C11 127.77(14) . . ? O1 C1 C11 119.50(14) . . ? N2 C2 O1 112.74(13) . . ? N2 C2 C21 128.06(14) . . ? O1 C2 C21 119.20(13) . . ? C4 C3 C14 112.10(14) . . ? C4 C3 C5 107.23(17) . . ? C14 C3 C5 111.42(14) . . ? C4 C3 C6 109.21(16) . . ? C14 C3 C6 107.45(14) . . ? C5 C3 C6 109.40(18) . . ? C3 C4 H41 111.7(12) . . ? C3 C4 H42 109.7(12) . . ? H41 C4 H42 107.7(17) . . ? C3 C4 H43 110.8(15) . . ? H41 C4 H43 111.9(18) . . ? H42 C4 H43 104.8(17) . . ? C3 C5 H51 106.6(12) . . ? C3 C5 H52 112.0(15) . . ? H51 C5 H52 107(2) . . ? C3 C5 H53 109.4(14) . . ? H51 C5 H53 108.7(18) . . ? H52 C5 H53 112(2) . . ? C3 C6 H61 111.6(14) . . ? C3 C6 H62 107.6(13) . . ? H61 C6 H62 107.2(19) . . ? C3 C6 H63 108.0(15) . . ? H61 C6 H63 110(2) . . ? H62 C6 H63 113(2) . . ? C8 C7 C24 179.89(19) . . ? C7 C8 C9 179.06(18) . . ? C10 C9 C8 178.30(18) . . ? C9 C10 C27 175.03(17) . . ? C16 C11 C12 118.65(15) . . ? C16 C11 C1 122.51(14) . . ? C12 C11 C1 118.84(14) . . ? C13 C12 C11 120.19(15) . . ? C13 C12 H12 120.4(12) . . ? C11 C12 H12 119.3(12) . . ? C12 C13 C14 122.09(15) . . ? C12 C13 H13 117.7(13) . . ? C14 C13 H13 120.1(13) . . ? C13 C14 C15 116.90(14) . . ? C13 C14 C3 120.87(14) . . ? C15 C14 C3 122.09(14) . . ? C16 C15 C14 121.55(16) . . ? C16 C15 H15 117.1(12) . . ? C14 C15 H15 121.4(12) . . ? C15 C16 C11 120.49(15) . . ? C15 C16 H16 120.2(13) . . ? C11 C16 H16 119.2(13) . . ? O2 C17 C18 108.01(17) . . ? O2 C17 H171 108.3(11) . . ? C18 C17 H171 110.3(12) . . ? O2 C17 H172 108.9(12) . . ? C18 C17 H172 110.1(12) . . ? H171 C17 H172 111.2(17) . . ? C17 C18 H181 111.6(15) . . ? C17 C18 H182 108.5(13) . . ? H181 C18 H182 105(2) . . ? C17 C18 H183 110.0(15) . . ? H181 C18 H183 110.0(19) . . ? H182 C18 H183 111.9(19) . . ? O3 C19 C20 106.98(15) . . ? O3 C19 H191 107.0(13) . . ? C20 C19 H191 110.4(13) . . ? O3 C19 H192 107.1(12) . . ? C20 C19 H192 112.4(12) . . ? H191 C19 H192 112.5(17) . . ? C19 C20 H201 108.5(14) . . ? C19 C20 H202 111.5(14) . . ? H201 C20 H202 108(2) . . ? C19 C20 H203 111.3(14) . . ? H201 C20 H203 110(2) . . ? H202 C20 H203 108(2) . . ? C26 C21 C22 119.97(14) . . ? C26 C21 C2 121.11(14) . . ? C22 C21 C2 118.92(14) . . ? C23 C22 C21 120.11(15) . . ? C23 C22 H22 119.4(12) . . ? C21 C22 H22 120.5(12) . . ? C22 C23 C24 120.15(15) . . ? C22 C23 H23 120.4(11) . . ? C24 C23 H23 119.4(11) . . ? C25 C24 C23 119.54(14) . . ? C25 C24 C7 119.96(15) . . ? C23 C24 C7 120.50(15) . . ? C26 C25 C24 120.10(15) . . ? C26 C25 H25 119.5(11) . . ? C24 C25 H25 120.4(11) . . ? C25 C26 C21 120.13(15) . . ? C25 C26 H26 118.2(12) . . ? C21 C26 H26 121.7(12) . . ? O2 C27 O3 107.66(12) . . ? O2 C27 C10 107.70(13) . . ? O3 C27 C10 110.10(13) . . ? O2 C27 H27 112.0(10) . . ? O3 C27 H27 108.5(10) . . ? C10 C27 H27 110.8(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.428 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.062 #=============================================END data_(5) _database_code_depnum_ccdc_archive 'CCDC 225630' _audit_creation_method SHELXL-97 _chemical_name_systematic ; {3-[5-(4-tert-Butylphenyl)-1,3,4-oxadiazol-2-yl]-phenyl}- propynal ; _chemical_name_common ? _chemical_melting_point '152--155\% C (decomp.)' _chemical_formula_moiety 'C21 H18 N2 O2' _chemical_formula_sum 'C21 H18 N2 O2' _chemical_formula_weight 330.37 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.945(2) _cell_length_b 6.183(1) _cell_length_c 23.460(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.94(1) _cell_angle_gamma 90.00 _cell_volume 1716.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 915 _cell_measurement_theta_min 10.24 _cell_measurement_theta_max 20.47 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 2.00 0.0350 1.00 0.00 -2.00 0.0350 0.00 0.00 1.00 0.0600 -1.00 0.00 0.00 0.1200 0.00 1.00 0.00 0.2000 0.00 -1.00 0.00 0.2000 _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (20 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.84 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19480 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3935 _reflns_number_gt 2788 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 2001)' _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. ; _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^)+(0.0969P)^2^+0.1289P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3935 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1606 _refine_ls_wR_factor_gt 0.1459 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 O1 O 0.27571(9) 0.18054(17) 0.38309(5) 0.0342(3) Uani 1 1 d . . . O2 O 0.42917(17) -0.4583(3) 0.77257(7) 0.0752(5) Uani 1 1 d . . . N1 N 0.34072(12) 0.5065(2) 0.36748(7) 0.0392(4) Uani 1 1 d . . . N2 N 0.37884(12) 0.4473(2) 0.42459(6) 0.0395(4) Uani 1 1 d . . . C1 C 0.28139(13) 0.3457(3) 0.34482(7) 0.0332(4) Uani 1 1 d . . . C2 C 0.33891(13) 0.2573(3) 0.43201(7) 0.0318(4) Uani 1 1 d . . . C3 C 0.04374(14) 0.2617(3) 0.11273(7) 0.0361(4) Uani 1 1 d . . . C4 C -0.06284(16) 0.1230(3) 0.10996(9) 0.0417(4) Uani 1 1 d . . . H41 H -0.0988(17) 0.116(3) 0.0688(9) 0.046(5) Uiso 1 1 d . . . H42 H -0.0468(18) -0.021(4) 0.1223(10) 0.053(6) Uiso 1 1 d . . . H43 H -0.1192(19) 0.187(3) 0.1332(9) 0.053(6) Uiso 1 1 d . . . C5 C 0.0081(2) 0.4818(3) 0.08586(9) 0.0500(5) Uani 1 1 d . . . H51 H 0.073(2) 0.573(4) 0.0820(10) 0.068(7) Uiso 1 1 d . . . H52 H -0.0352(19) 0.458(3) 0.0474(10) 0.055(6) Uiso 1 1 d . . . H53 H -0.040(2) 0.560(4) 0.1129(12) 0.074(8) Uiso 1 1 d . . . C6 C 0.12634(18) 0.1513(5) 0.07770(10) 0.0580(6) Uani 1 1 d . . . H61 H 0.0902(19) 0.136(4) 0.0381(10) 0.054(6) Uiso 1 1 d . . . H62 H 0.150(2) 0.001(4) 0.0943(11) 0.062(7) Uiso 1 1 d . . . H63 H 0.195(2) 0.242(4) 0.0775(10) 0.070(7) Uiso 1 1 d . . . C7 C 0.39055(15) -0.2686(3) 0.63202(8) 0.0399(4) Uani 1 1 d . . . C8 C 0.39989(16) -0.3829(3) 0.67409(8) 0.0440(4) Uani 1 1 d . . . C9 C 0.4132(2) -0.5218(4) 0.72413(10) 0.0546(5) Uani 1 1 d . . . H9 H 0.4143(19) -0.693(4) 0.7086(9) 0.061(6) Uiso 1 1 d . . . C11 C 0.21994(14) 0.3244(3) 0.28722(7) 0.0344(4) Uani 1 1 d . . . C12 C 0.15367(18) 0.1442(3) 0.27111(8) 0.0458(5) Uani 1 1 d . . . H12 H 0.146(2) 0.032(4) 0.2986(11) 0.069(7) Uiso 1 1 d . . . C13 C 0.09619(18) 0.1266(3) 0.21595(8) 0.0465(5) Uani 1 1 d . . . H13 H 0.055(2) 0.006(4) 0.2072(10) 0.062(7) Uiso 1 1 d . . . C14 C 0.10257(14) 0.2862(3) 0.17471(7) 0.0336(4) Uani 1 1 d . . . C15 C 0.16965(16) 0.4669(3) 0.19190(8) 0.0428(4) Uani 1 1 d . . . H15 H 0.1777(19) 0.582(4) 0.1628(10) 0.061(6) Uiso 1 1 d . . . C16 C 0.22695(17) 0.4866(3) 0.24683(8) 0.0430(4) Uani 1 1 d . . . H16 H 0.2725(18) 0.606(4) 0.2596(9) 0.052(6) Uiso 1 1 d . . . C21 C 0.35226(13) 0.1239(3) 0.48338(7) 0.0323(4) Uani 1 1 d . . . C22 C 0.30540(14) -0.0839(3) 0.48180(8) 0.0366(4) Uani 1 1 d . . . H22 H 0.2644(18) -0.136(3) 0.4453(9) 0.051(6) Uiso 1 1 d . . . C23 C 0.31830(15) -0.2099(3) 0.53051(8) 0.0384(4) Uani 1 1 d . . . H23 H 0.2830(18) -0.358(4) 0.5297(9) 0.053(6) Uiso 1 1 d . . . C24 C 0.37816(13) -0.1336(3) 0.58204(7) 0.0361(4) Uani 1 1 d . . . C25 C 0.42682(15) 0.0736(3) 0.58327(8) 0.0380(4) Uani 1 1 d . . . H25 H 0.4720(16) 0.118(3) 0.6182(9) 0.041(5) Uiso 1 1 d . . . C26 C 0.41409(14) 0.2003(3) 0.53434(8) 0.0362(4) Uani 1 1 d . . . H26 H 0.4484(16) 0.334(3) 0.5339(8) 0.035(5) 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 O1 0.0375(6) 0.0323(6) 0.0327(6) -0.0032(5) 0.0049(5) -0.0059(5) O2 0.0956(13) 0.0788(12) 0.0483(10) 0.0096(8) -0.0012(9) 0.0021(9) N1 0.0395(8) 0.0349(8) 0.0424(9) -0.0015(6) 0.0027(6) -0.0037(6) N2 0.0391(8) 0.0358(8) 0.0422(8) -0.0019(6) 0.0005(6) -0.0043(6) C1 0.0332(8) 0.0310(8) 0.0367(9) -0.0014(6) 0.0094(7) 0.0002(6) C2 0.0280(7) 0.0323(8) 0.0352(9) -0.0085(6) 0.0045(6) -0.0020(6) C3 0.0361(9) 0.0385(9) 0.0345(9) -0.0004(7) 0.0081(7) -0.0010(7) C4 0.0397(9) 0.0396(10) 0.0447(11) 0.0049(8) 0.0020(8) -0.0021(8) C5 0.0619(13) 0.0467(11) 0.0399(11) 0.0114(9) 0.0014(10) -0.0097(10) C6 0.0425(11) 0.0883(18) 0.0440(12) -0.0184(12) 0.0093(9) 0.0029(12) C7 0.0362(9) 0.0472(10) 0.0364(9) -0.0034(8) 0.0059(7) 0.0040(7) C8 0.0415(10) 0.0478(11) 0.0423(11) -0.0028(8) 0.0044(8) 0.0011(8) C9 0.0643(13) 0.0543(13) 0.0454(12) 0.0046(9) 0.0083(10) 0.0063(10) C11 0.0356(8) 0.0326(8) 0.0357(9) -0.0022(7) 0.0077(7) -0.0004(7) C12 0.0633(12) 0.0392(10) 0.0345(10) 0.0035(8) 0.0061(8) -0.0159(9) C13 0.0613(12) 0.0386(10) 0.0387(10) 0.0000(8) 0.0035(9) -0.0187(9) C14 0.0345(8) 0.0333(8) 0.0344(9) 0.0008(7) 0.0091(7) 0.0010(7) C15 0.0501(10) 0.0357(9) 0.0421(10) 0.0055(8) 0.0053(8) -0.0067(8) C16 0.0468(10) 0.0347(10) 0.0461(11) 0.0017(8) 0.0015(8) -0.0090(8) C21 0.0279(8) 0.0351(9) 0.0345(9) -0.0058(7) 0.0062(6) 0.0002(6) C22 0.0367(9) 0.0386(9) 0.0342(9) -0.0067(7) 0.0035(7) -0.0062(7) C23 0.0381(9) 0.0391(9) 0.0382(9) -0.0025(7) 0.0062(7) -0.0045(7) C24 0.0316(8) 0.0414(10) 0.0364(9) -0.0017(7) 0.0084(7) 0.0036(7) C25 0.0323(8) 0.0465(10) 0.0344(9) -0.0077(8) 0.0014(7) 0.0024(7) C26 0.0304(8) 0.0363(9) 0.0420(10) -0.0081(7) 0.0052(7) -0.0037(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.367(2) . ? O1 C2 1.3685(19) . ? O2 C9 1.192(3) . ? N1 C1 1.292(2) . ? N1 N2 1.403(2) . ? N2 C2 1.289(2) . ? C1 C11 1.452(2) . ? C2 C21 1.451(2) . ? C3 C4 1.529(2) . ? C3 C6 1.529(3) . ? C3 C14 1.533(2) . ? C3 C5 1.535(3) . ? C4 H41 1.00(2) . ? C4 H42 0.95(2) . ? C4 H43 1.00(2) . ? C5 H51 0.98(3) . ? C5 H52 0.99(2) . ? C5 H53 1.03(3) . ? C6 H61 0.97(2) . ? C6 H62 1.03(2) . ? C6 H63 1.00(3) . ? C7 C8 1.206(3) . ? C7 C24 1.430(2) . ? C8 C9 1.445(3) . ? C9 H9 1.12(2) . ? C11 C12 1.389(2) . ? C11 C16 1.390(2) . ? C12 C13 1.383(3) . ? C12 H12 0.96(2) . ? C13 C14 1.391(2) . ? C13 H13 0.90(2) . ? C14 C15 1.401(2) . ? C15 C16 1.379(3) . ? C15 H15 1.00(2) . ? C16 H16 0.94(2) . ? C21 C26 1.398(2) . ? C21 C22 1.400(2) . ? C22 C23 1.374(2) . ? C22 H22 0.98(2) . ? C23 C24 1.399(2) . ? C23 H23 1.01(2) . ? C24 C25 1.406(3) . ? C25 C26 1.381(3) . ? C25 H25 0.96(2) . ? C26 H26 0.925(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 102.71(12) . . ? C1 N1 N2 106.22(14) . . ? C2 N2 N1 106.83(13) . . ? N1 C1 O1 112.25(15) . . ? N1 C1 C11 129.11(15) . . ? O1 C1 C11 118.61(14) . . ? N2 C2 O1 111.99(15) . . ? N2 C2 C21 129.06(15) . . ? O1 C2 C21 118.95(14) . . ? C4 C3 C6 108.79(17) . . ? C4 C3 C14 111.45(14) . . ? C6 C3 C14 107.98(15) . . ? C4 C3 C5 107.33(16) . . ? C6 C3 C5 109.74(18) . . ? C14 C3 C5 111.53(15) . . ? C3 C4 H41 107.9(11) . . ? C3 C4 H42 112.5(13) . . ? H41 C4 H42 107.3(18) . . ? C3 C4 H43 111.9(12) . . ? H41 C4 H43 108.0(16) . . ? H42 C4 H43 109.1(18) . . ? C3 C5 H51 111.9(14) . . ? C3 C5 H52 108.9(12) . . ? H51 C5 H52 108.9(19) . . ? C3 C5 H53 107.9(14) . . ? H51 C5 H53 108(2) . . ? H52 C5 H53 111(2) . . ? C3 C6 H61 108.8(13) . . ? C3 C6 H62 111.4(14) . . ? H61 C6 H62 109.5(19) . . ? C3 C6 H63 110.1(14) . . ? H61 C6 H63 107.9(19) . . ? H62 C6 H63 109(2) . . ? C8 C7 C24 179.4(2) . . ? C7 C8 C9 178.8(2) . . ? O2 C9 C8 124.3(2) . . ? O2 C9 H9 127.9(11) . . ? C8 C9 H9 107.5(11) . . ? C12 C11 C16 118.63(17) . . ? C12 C11 C1 121.46(15) . . ? C16 C11 C1 119.91(15) . . ? C13 C12 C11 120.55(17) . . ? C13 C12 H12 119.2(15) . . ? C11 C12 H12 120.2(15) . . ? C12 C13 C14 121.82(17) . . ? C12 C13 H13 117.5(15) . . ? C14 C13 H13 120.7(15) . . ? C13 C14 C15 116.70(16) . . ? C13 C14 C3 121.86(15) . . ? C15 C14 C3 121.38(15) . . ? C16 C15 C14 121.99(17) . . ? C16 C15 H15 119.6(13) . . ? C14 C15 H15 118.4(13) . . ? C15 C16 C11 120.30(17) . . ? C15 C16 H16 123.9(13) . . ? C11 C16 H16 115.8(13) . . ? C26 C21 C22 119.68(16) . . ? C26 C21 C2 120.17(15) . . ? C22 C21 C2 120.13(15) . . ? C23 C22 C21 120.00(16) . . ? C23 C22 H22 121.8(12) . . ? C21 C22 H22 118.3(12) . . ? C22 C23 C24 120.84(17) . . ? C22 C23 H23 120.0(13) . . ? C24 C23 H23 119.1(13) . . ? C23 C24 C25 119.06(16) . . ? C23 C24 C7 119.63(17) . . ? C25 C24 C7 121.30(16) . . ? C26 C25 C24 120.16(16) . . ? C26 C25 H25 122.1(12) . . ? C24 C25 H25 117.6(12) . . ? C25 C26 C21 120.25(16) . . ? C25 C26 H26 121.3(11) . . ? C21 C26 H26 118.4(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.313 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.054 #===========================================END data_(11) _database_code_depnum_ccdc_archive 'CCDC 225631' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(3-{4-[5-(4-tert-Butylphenyl)-1,3,4-oxadiazol-2-yl]-phenyl}- prop-2-ynylidene)-1,3-dithiole-4,5-dicarboxylic acid dimethyl ester ; _chemical_name_common ? _chemical_melting_point '201--203\% C' _chemical_formula_moiety 'C28 H24 N2 O5 S2' _chemical_formula_sum 'C28 H24 N2 O5 S2' _chemical_formula_weight 532.61 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.878(1) _cell_length_b 11.000(1) _cell_length_c 12.705(1) _cell_angle_alpha 114.866(10) _cell_angle_beta 105.881(10) _cell_angle_gamma 97.048(10) _cell_volume 1276.48(19) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 920 _cell_measurement_theta_min 12.05 _cell_measurement_theta_max 26.14 _exptl_crystal_description prism _exptl_crystal_colour amber _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8950 _exptl_absorpt_correction_T_max 0.9712 _exptl_absorpt_process_details 'XPREP (SHELXTL)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 1.00 0.1900 0.00 1.00 -1.00 0.1900 1.00 0.00 1.00 0.1900 -1.00 0.00 -1.00 0.1900 -1.00 0.00 1.00 0.0850 1.00 0.00 -1.00 0.0850 _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.43 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15831 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 29.06 _reflns_number_total 6727 _reflns_number_gt 5969 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.060 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.060 (Bruker, 1999)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 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. ; _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^)+(0.0450P)^2^+0.4220P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6727 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0952 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 S1 S 0.69356(3) 1.14390(3) 0.69850(3) 0.02408(8) Uani 1 1 d . . . S2 S 0.49023(3) 0.88848(3) 0.61947(3) 0.02293(8) Uani 1 1 d . . . O1 O 0.21597(9) -0.03108(9) 0.04501(8) 0.02429(18) Uani 1 1 d . . . O2 O 0.69395(9) 1.39392(9) 0.90262(8) 0.0292(2) Uani 1 1 d . . . O4 O 0.28678(9) 1.07015(10) 0.75848(8) 0.02858(19) Uani 1 1 d . . . O3 O 0.53026(10) 1.30539(10) 0.94903(9) 0.0331(2) Uani 1 1 d . . . O5 O 0.40000(10) 0.97584(11) 0.86659(10) 0.0349(2) Uani 1 1 d . . . N1 N 0.04179(12) -0.10524(12) 0.08179(11) 0.0320(2) Uani 1 1 d . . . N2 N 0.09825(12) 0.03748(12) 0.16576(11) 0.0316(2) Uani 1 1 d . . . C1 C 0.11385(12) -0.14038(13) 0.01335(12) 0.0252(2) Uani 1 1 d . . . C2 C 0.19932(13) 0.07620(13) 0.14043(11) 0.0250(2) Uani 1 1 d . . . C3 C 0.00733(13) -0.67561(13) -0.41691(12) 0.0279(3) Uani 1 1 d . . . C4 C 0.08207(14) -0.67124(14) -0.50221(13) 0.0310(3) Uani 1 1 d . . . H41 H 0.1767(18) -0.6461(17) -0.4595(16) 0.034(4) Uiso 1 1 d . . . H42 H 0.0608(19) -0.603(2) -0.5283(17) 0.046(5) Uiso 1 1 d . . . H43 H 0.0550(18) -0.7646(19) -0.5787(17) 0.042(5) Uiso 1 1 d . . . C5 C -0.14266(14) -0.72248(17) -0.49275(14) 0.0368(3) Uani 1 1 d . . . H51 H -0.1679(17) -0.6556(18) -0.5220(16) 0.035(4) Uiso 1 1 d . . . H52 H -0.160(2) -0.812(2) -0.564(2) 0.057(6) Uiso 1 1 d . . . H53 H -0.1981(19) -0.735(2) -0.4476(17) 0.046(5) Uiso 1 1 d . . . C6 C 0.04328(18) -0.78239(16) -0.37408(17) 0.0410(3) Uani 1 1 d . . . H61 H 0.138(2) -0.7562(19) -0.3301(17) 0.043(5) Uiso 1 1 d . . . H62 H 0.0194(19) -0.874(2) -0.4467(19) 0.050(5) Uiso 1 1 d . . . H63 H -0.003(2) -0.791(2) -0.3219(19) 0.052(5) Uiso 1 1 d . . . C7 C 0.53612(13) 0.62494(13) 0.36925(11) 0.0266(2) Uani 1 1 d . . . C8 C 0.59836(13) 0.74567(13) 0.42498(11) 0.0262(2) Uani 1 1 d . . . C9 C 0.66323(12) 0.88990(13) 0.50118(11) 0.0256(2) Uani 1 1 d . . . H9 H 0.7360(17) 0.9339(17) 0.4898(15) 0.033(4) Uiso 1 1 d . . . C10 C 0.62281(12) 0.96627(12) 0.59443(11) 0.0223(2) Uani 1 1 d . . . C11 C 0.09525(12) -0.27541(13) -0.09060(12) 0.0255(2) Uani 1 1 d . . . C12 C 0.17423(12) -0.29432(13) -0.16281(12) 0.0249(2) Uani 1 1 d . . . H12 H 0.2470(17) -0.2206(18) -0.1408(15) 0.035(4) Uiso 1 1 d . . . C13 C 0.14691(12) -0.42263(13) -0.26700(12) 0.0253(2) Uani 1 1 d . . . H13 H 0.2010(16) -0.4338(17) -0.3164(15) 0.030(4) Uiso 1 1 d . . . C14 C 0.04154(12) -0.53457(12) -0.30161(11) 0.0250(2) Uani 1 1 d . . . C15 C -0.03296(14) -0.51491(15) -0.22430(14) 0.0355(3) Uani 1 1 d . . . H15 H -0.1032(18) -0.5899(19) -0.2420(17) 0.042(5) Uiso 1 1 d . . . C16 C -0.00720(15) -0.38805(15) -0.12106(14) 0.0370(3) Uani 1 1 d . . . H16 H -0.059(2) -0.372(2) -0.0714(19) 0.053(5) Uiso 1 1 d . . . C17 C 0.58383(12) 1.15759(12) 0.77865(10) 0.0221(2) Uani 1 1 d . . . C18 C 0.49117(12) 1.04075(12) 0.74136(10) 0.0216(2) Uani 1 1 d . . . C19 C 0.59727(12) 1.29202(12) 0.88540(11) 0.0239(2) Uani 1 1 d . . . C20 C 0.38946(12) 1.02690(12) 0.79884(11) 0.0234(2) Uani 1 1 d . . . C21 C 0.28930(12) 0.21484(13) 0.19819(11) 0.0241(2) Uani 1 1 d . . . C22 C 0.39173(13) 0.24135(13) 0.15722(11) 0.0254(2) Uani 1 1 d . . . H22 H 0.4072(17) 0.1704(18) 0.0939(16) 0.035(4) Uiso 1 1 d . . . C23 C 0.47328(13) 0.37525(13) 0.21236(11) 0.0262(2) Uani 1 1 d . . . H23 H 0.5423(17) 0.3917(18) 0.1844(16) 0.035(4) Uiso 1 1 d . . . C24 C 0.45557(12) 0.48449(13) 0.31067(11) 0.0246(2) Uani 1 1 d . . . C25 C 0.35515(14) 0.45589(14) 0.35323(13) 0.0327(3) Uani 1 1 d . . . H25 H 0.3418(19) 0.525(2) 0.4164(17) 0.044(5) Uiso 1 1 d . . . C26 C 0.27253(15) 0.32302(15) 0.29728(13) 0.0329(3) Uani 1 1 d . . . H26 H 0.207(2) 0.304(2) 0.3246(18) 0.051(5) Uiso 1 1 d . . . C27 C 0.71642(17) 1.52829(14) 1.00892(14) 0.0356(3) Uani 1 1 d . . . H271 H 0.633(2) 1.5571(19) 1.0008(17) 0.045(5) Uiso 1 1 d . . . H272 H 0.746(2) 1.520(2) 1.084(2) 0.062(6) Uiso 1 1 d . . . H273 H 0.778(2) 1.590(3) 1.006(2) 0.072(7) Uiso 1 1 d . . . C28 C 0.18346(15) 1.06002(18) 0.80955(15) 0.0344(3) Uani 1 1 d . . . H281 H 0.1547(19) 0.970(2) 0.7972(17) 0.047(5) Uiso 1 1 d . . . H282 H 0.215(2) 1.119(2) 0.897(2) 0.054(6) Uiso 1 1 d . . . H283 H 0.117(2) 1.084(2) 0.770(2) 0.058(6) 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 S1 0.02363(14) 0.02107(14) 0.02359(14) 0.00638(11) 0.01141(11) 0.00235(11) S2 0.02424(15) 0.02006(14) 0.02279(14) 0.00831(11) 0.01010(11) 0.00377(10) O1 0.0251(4) 0.0217(4) 0.0245(4) 0.0088(3) 0.0107(3) 0.0054(3) O2 0.0325(5) 0.0215(4) 0.0259(4) 0.0048(3) 0.0128(4) 0.0014(3) O4 0.0265(4) 0.0375(5) 0.0318(5) 0.0214(4) 0.0160(4) 0.0108(4) O3 0.0376(5) 0.0287(5) 0.0297(5) 0.0072(4) 0.0199(4) 0.0057(4) O5 0.0379(5) 0.0445(6) 0.0395(5) 0.0292(5) 0.0215(4) 0.0165(4) N1 0.0304(6) 0.0291(5) 0.0322(6) 0.0097(5) 0.0149(5) 0.0042(4) N2 0.0314(6) 0.0293(5) 0.0316(6) 0.0102(5) 0.0157(5) 0.0059(5) C1 0.0224(5) 0.0247(6) 0.0263(6) 0.0112(5) 0.0082(5) 0.0039(4) C2 0.0275(6) 0.0253(6) 0.0219(5) 0.0099(5) 0.0100(5) 0.0093(5) C3 0.0263(6) 0.0216(5) 0.0310(6) 0.0092(5) 0.0098(5) 0.0039(5) C4 0.0279(6) 0.0276(6) 0.0318(7) 0.0085(5) 0.0120(5) 0.0065(5) C5 0.0263(6) 0.0361(7) 0.0334(7) 0.0079(6) 0.0082(5) -0.0010(5) C6 0.0504(10) 0.0269(7) 0.0491(9) 0.0190(7) 0.0201(8) 0.0134(6) C7 0.0283(6) 0.0266(6) 0.0236(6) 0.0092(5) 0.0107(5) 0.0108(5) C8 0.0264(6) 0.0269(6) 0.0240(6) 0.0091(5) 0.0108(5) 0.0100(5) C9 0.0239(6) 0.0249(6) 0.0255(6) 0.0089(5) 0.0110(5) 0.0059(5) C10 0.0218(5) 0.0210(5) 0.0216(5) 0.0085(4) 0.0074(4) 0.0046(4) C11 0.0249(6) 0.0227(5) 0.0274(6) 0.0108(5) 0.0101(5) 0.0043(4) C12 0.0240(6) 0.0222(5) 0.0277(6) 0.0123(5) 0.0091(5) 0.0026(4) C13 0.0249(6) 0.0245(6) 0.0263(6) 0.0118(5) 0.0103(5) 0.0045(5) C14 0.0235(6) 0.0217(5) 0.0271(6) 0.0106(5) 0.0075(5) 0.0045(4) C15 0.0308(7) 0.0274(6) 0.0410(8) 0.0093(6) 0.0181(6) -0.0021(5) C16 0.0342(7) 0.0311(7) 0.0401(8) 0.0090(6) 0.0223(6) -0.0001(6) C17 0.0235(5) 0.0235(5) 0.0192(5) 0.0089(4) 0.0096(4) 0.0061(4) C18 0.0230(5) 0.0232(5) 0.0191(5) 0.0097(4) 0.0089(4) 0.0067(4) C19 0.0252(6) 0.0224(5) 0.0210(5) 0.0084(4) 0.0079(4) 0.0051(4) C20 0.0254(6) 0.0221(5) 0.0217(5) 0.0089(4) 0.0103(4) 0.0043(4) C21 0.0255(6) 0.0244(5) 0.0219(5) 0.0103(5) 0.0082(4) 0.0082(5) C22 0.0279(6) 0.0244(6) 0.0216(5) 0.0071(5) 0.0111(5) 0.0091(5) C23 0.0269(6) 0.0269(6) 0.0232(6) 0.0091(5) 0.0114(5) 0.0072(5) C24 0.0259(6) 0.0237(5) 0.0212(5) 0.0087(5) 0.0067(4) 0.0083(5) C25 0.0360(7) 0.0276(6) 0.0300(6) 0.0056(5) 0.0182(6) 0.0100(5) C26 0.0346(7) 0.0307(7) 0.0327(7) 0.0097(5) 0.0199(6) 0.0082(5) C27 0.0407(8) 0.0216(6) 0.0324(7) 0.0029(5) 0.0150(6) 0.0019(5) C28 0.0293(7) 0.0484(8) 0.0416(8) 0.0290(7) 0.0216(6) 0.0151(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C10 1.7492(12) . ? S1 C17 1.7507(12) . ? S2 C18 1.7348(12) . ? S2 C10 1.7580(12) . ? O1 C1 1.3646(15) . ? O1 C2 1.3655(15) . ? O2 C19 1.3375(15) . ? O2 C27 1.4561(16) . ? O4 C20 1.3262(15) . ? O4 C28 1.4580(15) . ? O3 C19 1.2064(15) . ? O5 C20 1.1991(15) . ? N1 C1 1.2980(17) . ? N1 N2 1.4058(16) . ? N2 C2 1.2991(17) . ? C1 C11 1.4565(17) . ? C2 C21 1.4566(17) . ? C3 C14 1.5297(17) . ? C3 C4 1.5343(19) . ? C3 C6 1.537(2) . ? C3 C5 1.5400(19) . ? C4 H41 0.964(18) . ? C4 H42 0.96(2) . ? C4 H43 1.008(18) . ? C5 H51 0.989(18) . ? C5 H52 0.97(2) . ? C5 H53 0.97(2) . ? C6 H61 0.97(2) . ? C6 H62 0.98(2) . ? C6 H63 0.96(2) . ? C7 C8 1.2040(18) . ? C7 C24 1.4326(18) . ? C8 C9 1.4185(17) . ? C9 C10 1.3570(17) . ? C9 H9 0.954(17) . ? C11 C12 1.3921(17) . ? C11 C16 1.3960(18) . ? C12 C13 1.3940(17) . ? C12 H12 0.945(17) . ? C13 C14 1.3950(17) . ? C13 H13 0.954(17) . ? C14 C15 1.4029(19) . ? C15 C16 1.382(2) . ? C15 H15 0.954(19) . ? C16 H16 0.94(2) . ? C17 C18 1.3420(17) . ? C17 C19 1.4830(16) . ? C18 C20 1.5084(16) . ? C21 C26 1.3977(18) . ? C21 C22 1.4010(18) . ? C22 C23 1.3851(18) . ? C22 H22 0.929(17) . ? C23 C24 1.4027(17) . ? C23 H23 0.943(18) . ? C24 C25 1.4023(19) . ? C25 C26 1.380(2) . ? C25 H25 0.904(19) . ? C26 H26 0.91(2) . ? C27 H271 0.99(2) . ? C27 H272 0.97(2) . ? C27 H273 0.92(3) . ? C28 H281 0.94(2) . ? C28 H282 0.95(2) . ? C28 H283 0.90(2) . ? 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 C10 S1 C17 95.45(6) . . ? C18 S2 C10 95.37(6) . . ? C1 O1 C2 102.71(10) . . ? C19 O2 C27 114.55(11) . . ? C20 O4 C28 114.66(10) . . ? C1 N1 N2 106.24(11) . . ? C2 N2 N1 106.26(11) . . ? N1 C1 O1 112.45(11) . . ? N1 C1 C11 128.41(12) . . ? O1 C1 C11 119.11(11) . . ? N2 C2 O1 112.34(11) . . ? N2 C2 C21 128.31(12) . . ? O1 C2 C21 119.33(11) . . ? C14 C3 C4 112.70(11) . . ? C14 C3 C6 108.45(11) . . ? C4 C3 C6 108.92(12) . . ? C14 C3 C5 109.49(11) . . ? C4 C3 C5 108.02(12) . . ? C6 C3 C5 109.21(12) . . ? C3 C4 H41 110.9(10) . . ? C3 C4 H42 109.2(12) . . ? H41 C4 H42 109.0(15) . . ? C3 C4 H43 110.8(10) . . ? H41 C4 H43 108.6(14) . . ? H42 C4 H43 108.3(15) . . ? C3 C5 H51 110.6(10) . . ? C3 C5 H52 106.6(13) . . ? H51 C5 H52 108.7(15) . . ? C3 C5 H53 113.8(11) . . ? H51 C5 H53 109.0(15) . . ? H52 C5 H53 108.0(17) . . ? C3 C6 H61 109.7(11) . . ? C3 C6 H62 109.3(12) . . ? H61 C6 H62 107.7(16) . . ? C3 C6 H63 112.5(12) . . ? H61 C6 H63 109.7(16) . . ? H62 C6 H63 107.8(17) . . ? C8 C7 C24 174.73(14) . . ? C7 C8 C9 172.81(14) . . ? C10 C9 C8 119.15(12) . . ? C10 C9 H9 119.2(10) . . ? C8 C9 H9 121.6(10) . . ? C9 C10 S1 125.09(10) . . ? C9 C10 S2 120.61(9) . . ? S1 C10 S2 114.30(7) . . ? C12 C11 C16 119.03(12) . . ? C12 C11 C1 121.83(11) . . ? C16 C11 C1 119.11(12) . . ? C11 C12 C13 120.00(11) . . ? C11 C12 H12 120.1(10) . . ? C13 C12 H12 119.9(10) . . ? C12 C13 C14 121.63(12) . . ? C12 C13 H13 119.2(10) . . ? C14 C13 H13 119.2(10) . . ? C13 C14 C15 117.31(12) . . ? C13 C14 C3 122.83(11) . . ? C15 C14 C3 119.85(11) . . ? C16 C15 C14 121.54(12) . . ? C16 C15 H15 118.2(11) . . ? C14 C15 H15 120.3(11) . . ? C15 C16 C11 120.37(13) . . ? C15 C16 H16 122.3(13) . . ? C11 C16 H16 117.2(13) . . ? C18 C17 C19 122.31(11) . . ? C18 C17 S1 116.93(9) . . ? C19 C17 S1 120.72(9) . . ? C17 C18 C20 126.15(10) . . ? C17 C18 S2 117.89(9) . . ? C20 C18 S2 115.92(8) . . ? O3 C19 O2 125.07(11) . . ? O3 C19 C17 123.55(11) . . ? O2 C19 C17 111.37(10) . . ? O5 C20 O4 125.99(12) . . ? O5 C20 C18 122.75(11) . . ? O4 C20 C18 111.14(10) . . ? C26 C21 C22 119.75(12) . . ? C26 C21 C2 118.65(12) . . ? C22 C21 C2 121.60(11) . . ? C23 C22 C21 119.97(11) . . ? C23 C22 H22 118.7(11) . . ? C21 C22 H22 121.3(11) . . ? C22 C23 C24 120.43(12) . . ? C22 C23 H23 119.2(10) . . ? C24 C23 H23 120.3(10) . . ? C25 C24 C23 119.06(12) . . ? C25 C24 C7 118.54(11) . . ? C23 C24 C7 122.40(12) . . ? C26 C25 C24 120.62(12) . . ? C26 C25 H25 118.7(12) . . ? C24 C25 H25 120.6(12) . . ? C25 C26 C21 120.13(13) . . ? C25 C26 H26 120.8(13) . . ? C21 C26 H26 119.1(13) . . ? O2 C27 H271 109.8(11) . . ? O2 C27 H272 108.5(13) . . ? H271 C27 H272 110.4(17) . . ? O2 C27 H273 105.9(15) . . ? H271 C27 H273 109.1(18) . . ? H272 C27 H273 113(2) . . ? O4 C28 H281 111.1(12) . . ? O4 C28 H282 111.6(13) . . ? H281 C28 H282 105.7(17) . . ? O4 C28 H283 105.8(14) . . ? H281 C28 H283 111.4(18) . . ? H282 C28 H283 111.4(18) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.434 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.050 #==========================================END