Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_year 2006 _publ_contact_author M.Bryce _publ_contact_author_email M.R.BRYCE@DURHAM.AC.UK _journal_volume ? _journal_page_first ? _journal_page_last ? _database_code_depnum_ccdc_journal ? _publ_section_title ; New electroluminescent bipolar compounds for balanced charge-transport and tuneable colour in single-layer organic light emitting diodes: triphenylamine-oxadiazole-fluorene triad molecules ; _publ_contact_author_name M.Bryce loop_ _publ_author_name K.T.Kamtekar C.Wang S.Bettington A.S.Batsanov I.F.Perepichka ; M.R.Bryce ; J.H.Ahn M.Rabinal M.C.Petty #=====================================END data_(12) _database_code_depnum_ccdc_archive 'CCDC 602976' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(4-tert-Butylphenyl)-5-{4-[9,9-dihexyl-2-(trimethylsilyl)-fluoren-7- yl]phenyl}-1,3,4-oxadiazole ; _chemical_name_common ; 2-(4-tert-Butylphenyl)-5-(4-(9,9-dihexyl-2-(trimethylsilyl)- fluoren-7-yl)phenyl)-1,3,4-oxadiazole ; _chemical_melting_point 417.6(4) _chemical_formula_moiety 'C46 H58 N2 O Si' _chemical_formula_sum 'C46 H58 N2 O Si' _chemical_formula_weight 683.03 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 14.695(2) _cell_length_b 13.3300(14) _cell_length_c 41.182(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.32(1) _cell_angle_gamma 90.00 _cell_volume 8044(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 848 _cell_measurement_theta_min 10.25 _cell_measurement_theta_max 19.24 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.128 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2960 _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 ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 -1.00 1.00 0.0650 1.00 1.00 -1.00 0.0650 1.00 -1.00 0.00 0.0700 -1.00 1.00 0.00 0.0700 0.00 0.00 1.00 0.0150 0.00 0.00 -1.00 0.0150 _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 (45 sec exposure) covering 0.3\% in \w. Crystal to detector distance 6.84 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 'Bruker SMART 6K CCD area detector' _diffrn_measurement_method '\W scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_reflns_number 34477 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7093 _reflns_number_gt 4312 _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 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _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^)+(0.0566P)^2^] 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 7093 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _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 Si Si -0.08774(5) 0.27706(5) 0.532489(16) 0.03373(19) Uani 1 1 d . . . O O 0.74757(10) 0.55596(10) 0.75457(3) 0.0278(4) Uani 1 1 d . . . N1 N 0.71142(13) 0.71245(14) 0.74123(4) 0.0332(5) Uani 1 1 d . . . N2 N 0.79884(13) 0.71200(14) 0.75792(4) 0.0336(5) Uani 1 1 d . . . C1 C 0.05794(15) 0.38443(17) 0.56743(5) 0.0302(5) Uani 1 1 d . . . H1 H 0.0508 0.4325 0.5504 0.036 Uiso 1 1 d R . . C2 C 0.00149(15) 0.29937(16) 0.56657(5) 0.0298(5) Uani 1 1 d . . . C3 C 0.01473(15) 0.23046(17) 0.59211(5) 0.0315(6) Uani 1 1 d . . . H3 H -0.0228 0.1724 0.5919 0.038 Uiso 1 1 d R . . C4 C 0.08005(15) 0.24347(16) 0.61760(5) 0.0294(5) Uani 1 1 d . . . H4 H 0.0874 0.1953 0.6346 0.035 Uiso 1 1 d R . . C5 C 0.24846(15) 0.31975(16) 0.66934(5) 0.0288(5) Uani 1 1 d . . . H5 H 0.2241 0.2597 0.6776 0.035 Uiso 1 1 d R . . C6 C 0.32198(15) 0.36677(16) 0.68573(5) 0.0290(5) Uani 1 1 d . . . H6 H 0.3479 0.3383 0.7055 0.035 Uiso 1 1 d R . . C7 C 0.35939(15) 0.45469(16) 0.67418(5) 0.0259(5) Uani 1 1 d . . . C8 C 0.31935(15) 0.49774(16) 0.64564(5) 0.0273(5) Uani 1 1 d . . . H8 H 0.3426 0.5588 0.6378 0.033 Uiso 1 1 d R . . C9 C 0.19484(15) 0.48245(15) 0.59692(5) 0.0258(5) Uani 1 1 d . . . C10 C 0.12384(15) 0.39913(16) 0.59276(5) 0.0267(5) Uani 1 1 d . . . C11 C 0.13524(15) 0.32869(16) 0.61789(5) 0.0264(5) Uani 1 1 d . . . C12 C 0.21082(15) 0.36188(16) 0.64056(5) 0.0254(5) Uani 1 1 d . . . C13 C 0.24605(15) 0.45149(15) 0.62895(5) 0.0252(5) Uani 1 1 d . . . C14 C 0.15223(15) 0.58803(16) 0.59846(5) 0.0279(5) Uani 1 1 d . . . H14A H 0.2021 0.6370 0.6033 0.036 Uiso 1 1 d R . . H14B H 0.1232 0.6045 0.5766 0.036 Uiso 1 1 d R . . C15 C 0.08148(16) 0.60263(17) 0.62335(6) 0.0336(6) Uani 1 1 d . . . H15A H 0.0360 0.5478 0.6210 0.044 Uiso 1 1 d R . . H15B H 0.1121 0.5986 0.6456 0.044 Uiso 1 1 d R . . C16 C 0.03233(16) 0.70318(17) 0.61924(6) 0.0365(6) Uani 1 1 d . . . H16A H 0.0114 0.7118 0.5960 0.047 Uiso 1 1 d R . . H16B H -0.0225 0.7015 0.6318 0.047 Uiso 1 1 d R . . C17 C 0.08959(17) 0.79330(18) 0.63008(6) 0.0414(6) Uani 1 1 d . . . H17A H 0.1500 0.7877 0.6211 0.054 Uiso 1 1 d R . . H17B H 0.0995 0.7925 0.6541 0.054 Uiso 1 1 d R . . C18 C 0.04635(18) 0.89360(19) 0.61944(6) 0.0459(7) Uani 1 1 d . . . H18A H -0.0194 0.8920 0.6232 0.060 Uiso 1 1 d R . . H18B H 0.0750 0.9478 0.6331 0.060 Uiso 1 1 d R . . C19 C 0.0566(2) 0.9174(2) 0.58419(7) 0.0663(9) Uani 1 1 d . . . H19A H 0.1212 0.9277 0.5808 0.082(6) Uiso 1 1 d R . . H19B H 0.0222 0.9784 0.5781 0.082(6) Uiso 1 1 d R . . H19C H 0.0329 0.8614 0.5706 0.082(6) Uiso 1 1 d R . . C20 C 0.25755(16) 0.48123(16) 0.56839(5) 0.0305(6) Uani 1 1 d . . . H20A H 0.2220 0.5060 0.5486 0.040 Uiso 1 1 d R . . H20B H 0.3082 0.5291 0.5734 0.040 Uiso 1 1 d R . . C21 C 0.29832(17) 0.38003(17) 0.56060(5) 0.0352(6) Uani 1 1 d . . . H21A H 0.2503 0.3280 0.5612 0.046 Uiso 1 1 d R . . H21B H 0.3470 0.3634 0.5777 0.046 Uiso 1 1 d R . . C22 C 0.33822(17) 0.37678(18) 0.52746(5) 0.0377(6) Uani 1 1 d . . . H22A H 0.3861 0.4289 0.5270 0.049 Uiso 1 1 d R . . H22B H 0.3680 0.3109 0.5250 0.049 Uiso 1 1 d R . . C23 C 0.26960(18) 0.39289(19) 0.49838(5) 0.0423(6) Uani 1 1 d . . . H23A H 0.2192 0.3441 0.4997 0.055 Uiso 1 1 d R . . H23B H 0.2433 0.4610 0.4999 0.055 Uiso 1 1 d R . . C24 C 0.3088(2) 0.3819(2) 0.46550(6) 0.0495(7) Uani 1 1 d . . . H24A H 0.3585 0.4315 0.4640 0.064 Uiso 1 1 d R . . H24B H 0.3358 0.3142 0.4641 0.064 Uiso 1 1 d R . . C25 C 0.2395(2) 0.3967(2) 0.43682(6) 0.0589(9) Uani 1 1 d . . . H25A H 0.1875 0.3517 0.4389 0.064(5) Uiso 1 1 d R . . H25B H 0.2678 0.3816 0.4166 0.064(5) Uiso 1 1 d R . . H25C H 0.2182 0.4664 0.4363 0.064(5) Uiso 1 1 d R . . C26 C 0.44242(15) 0.49946(17) 0.69139(5) 0.0273(5) Uani 1 1 d . . . C27 C 0.45611(16) 0.60284(17) 0.69388(5) 0.0315(6) Uani 1 1 d . . . H27 H 0.4111 0.6472 0.6844 0.038 Uiso 1 1 d R . . C28 C 0.53411(16) 0.64151(17) 0.70995(5) 0.0337(6) Uani 1 1 d . . . H28 H 0.5419 0.7121 0.7116 0.040 Uiso 1 1 d R . . C29 C 0.60161(15) 0.57796(17) 0.72381(5) 0.0271(5) Uani 1 1 d . . . C30 C 0.58923(15) 0.47464(16) 0.72122(5) 0.0289(6) Uani 1 1 d . . . H30 H 0.6346 0.4302 0.7305 0.035 Uiso 1 1 d R . . C31 C 0.51109(15) 0.43708(17) 0.70524(5) 0.0310(6) Uani 1 1 d . . . H31 H 0.5036 0.3664 0.7036 0.037 Uiso 1 1 d R . . C32 C 0.68464(15) 0.62014(16) 0.73971(5) 0.0268(5) Uani 1 1 d . . . C33 C 0.81720(15) 0.61935(16) 0.76513(5) 0.0278(5) Uani 1 1 d . . . C34 C 0.89916(15) 0.57687(16) 0.78184(5) 0.0269(5) Uani 1 1 d . . . C35 C 0.97420(16) 0.63790(17) 0.78922(5) 0.0316(6) Uani 1 1 d . . . H35 H 0.9715 0.7068 0.7833 0.038 Uiso 1 1 d R . . C36 C 1.05261(16) 0.60024(17) 0.80506(5) 0.0309(6) Uani 1 1 d . . . H36 H 1.1032 0.6437 0.8098 0.037 Uiso 1 1 d R . . C37 C 1.05973(15) 0.49965(17) 0.81438(5) 0.0270(5) Uani 1 1 d . . . C38 C 0.98314(15) 0.43923(17) 0.80681(5) 0.0312(6) Uani 1 1 d . . . H38 H 0.9854 0.3706 0.8130 0.037 Uiso 1 1 d R . . C39 C 0.90440(16) 0.47614(16) 0.79066(5) 0.0302(6) Uani 1 1 d . . . H39 H 0.8540 0.4329 0.7856 0.036 Uiso 1 1 d R . . C40 C 1.14626(15) 0.45373(17) 0.83100(5) 0.0326(6) Uani 1 1 d . . . C41 C 1.18377(16) 0.37645(18) 0.80782(6) 0.0388(6) Uani 1 1 d . . . H41A H 1.1384 0.3234 0.8032 0.048(4) Uiso 1 1 d R . . H41B H 1.2400 0.3470 0.8180 0.048(4) Uiso 1 1 d R . . H41C H 1.1969 0.4095 0.7874 0.048(4) Uiso 1 1 d R . . C42 C 1.12520(17) 0.4017(2) 0.86269(6) 0.0505(8) Uani 1 1 d . . . H42A H 1.1022 0.4511 0.8777 0.059(5) Uiso 1 1 d R . . H42B H 1.1810 0.3709 0.8727 0.059(5) Uiso 1 1 d R . . H42C H 1.0789 0.3497 0.8580 0.059(5) Uiso 1 1 d R . . C43 C 1.22023(16) 0.53328(19) 0.83914(6) 0.0421(7) Uani 1 1 d . . . H43A H 1.2370 0.5651 0.8190 0.045(4) Uiso 1 1 d R . . H43B H 1.2741 0.5013 0.8501 0.045(4) Uiso 1 1 d R . . H43C H 1.1967 0.5842 0.8535 0.045(4) Uiso 1 1 d R . . C44 C -0.07470(18) 0.14845(19) 0.51604(6) 0.0466(7) Uani 1 1 d . . . H44A H -0.0186 0.1448 0.5046 0.069(5) Uiso 1 1 d R . . H44B H -0.1272 0.1327 0.5008 0.069(5) Uiso 1 1 d R . . H44C H -0.0714 0.1000 0.5340 0.069(5) Uiso 1 1 d R . . C45 C -0.07550(19) 0.3708(2) 0.49986(6) 0.0517(8) Uani 1 1 d . . . H45A H -0.0808 0.4385 0.5088 0.076(5) Uiso 1 1 d R . . H45B H -0.1236 0.3605 0.4824 0.076(5) Uiso 1 1 d R . . H45C H -0.0156 0.3631 0.4911 0.076(5) Uiso 1 1 d R . . C46 C -0.20238(17) 0.2887(2) 0.54869(6) 0.0485(7) Uani 1 1 d . . . H46A H -0.2055 0.2446 0.5676 0.081(6) Uiso 1 1 d R . . H46B H -0.2495 0.2692 0.5318 0.081(6) Uiso 1 1 d R . . H46C H -0.2123 0.3583 0.5552 0.081(6) Uiso 1 1 d 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 Si 0.0377(4) 0.0328(4) 0.0306(4) 0.0017(3) 0.0022(3) -0.0072(3) O 0.0324(9) 0.0246(8) 0.0262(8) 0.0014(7) 0.0011(7) -0.0013(7) N1 0.0414(12) 0.0286(12) 0.0295(11) 0.0033(9) 0.0010(9) 0.0008(10) N2 0.0420(13) 0.0275(12) 0.0306(11) 0.0031(9) -0.0008(9) -0.0004(9) C1 0.0373(14) 0.0302(13) 0.0234(12) 0.0040(10) 0.0045(10) -0.0023(11) C2 0.0347(14) 0.0288(13) 0.0269(13) -0.0001(10) 0.0080(10) -0.0025(11) C3 0.0366(14) 0.0265(13) 0.0320(13) 0.0007(11) 0.0072(11) -0.0039(11) C4 0.0384(14) 0.0241(13) 0.0269(13) 0.0047(10) 0.0096(11) -0.0002(11) C5 0.0361(14) 0.0236(12) 0.0278(13) 0.0044(10) 0.0085(10) 0.0033(11) C6 0.0340(14) 0.0297(13) 0.0236(12) 0.0051(10) 0.0042(10) 0.0078(11) C7 0.0320(14) 0.0250(13) 0.0215(12) -0.0006(10) 0.0073(10) 0.0084(10) C8 0.0358(14) 0.0211(12) 0.0260(12) 0.0002(10) 0.0083(10) 0.0028(10) C9 0.0350(14) 0.0231(12) 0.0197(11) 0.0034(9) 0.0036(10) -0.0013(10) C10 0.0330(13) 0.0248(12) 0.0229(12) 0.0005(10) 0.0063(10) -0.0001(10) C11 0.0332(14) 0.0254(12) 0.0215(12) -0.0001(10) 0.0082(10) 0.0039(10) C12 0.0312(13) 0.0236(12) 0.0223(12) 0.0010(10) 0.0077(10) 0.0045(10) C13 0.0312(13) 0.0236(12) 0.0215(12) -0.0005(10) 0.0058(10) 0.0042(10) C14 0.0337(14) 0.0277(13) 0.0223(12) 0.0034(10) 0.0021(10) -0.0016(10) C15 0.0377(15) 0.0305(14) 0.0336(13) 0.0056(11) 0.0090(11) 0.0009(11) C16 0.0327(14) 0.0389(15) 0.0389(14) 0.0065(12) 0.0088(11) 0.0020(11) C17 0.0417(16) 0.0408(16) 0.0420(15) -0.0057(12) 0.0062(12) 0.0025(12) C18 0.0431(16) 0.0380(16) 0.0578(18) -0.0039(13) 0.0128(13) 0.0055(13) C19 0.073(2) 0.051(2) 0.078(2) 0.0242(17) 0.0274(18) 0.0138(16) C20 0.0410(15) 0.0271(13) 0.0243(12) 0.0008(10) 0.0088(10) -0.0027(11) C21 0.0447(16) 0.0311(14) 0.0310(13) 0.0020(11) 0.0104(11) -0.0023(11) C22 0.0446(16) 0.0345(14) 0.0349(14) -0.0033(11) 0.0084(12) 0.0002(12) C23 0.0571(18) 0.0367(15) 0.0341(14) -0.0018(12) 0.0092(12) 0.0025(13) C24 0.078(2) 0.0409(16) 0.0311(15) -0.0022(12) 0.0127(14) -0.0070(14) C25 0.104(3) 0.0410(17) 0.0321(15) 0.0003(13) 0.0066(16) 0.0120(16) C26 0.0329(14) 0.0299(13) 0.0195(11) 0.0014(10) 0.0050(10) 0.0052(11) C27 0.0391(15) 0.0292(14) 0.0258(12) 0.0025(10) -0.0006(11) 0.0077(11) C28 0.0491(16) 0.0232(13) 0.0283(13) -0.0011(10) -0.0007(12) 0.0022(11) C29 0.0341(14) 0.0291(13) 0.0186(11) 0.0005(10) 0.0058(10) 0.0039(10) C30 0.0307(14) 0.0289(14) 0.0273(12) 0.0046(10) 0.0036(10) 0.0045(10) C31 0.0384(15) 0.0224(12) 0.0324(13) 0.0021(10) 0.0052(11) 0.0018(11) C32 0.0374(14) 0.0254(13) 0.0179(11) 0.0038(10) 0.0047(10) 0.0051(11) C33 0.0379(15) 0.0255(13) 0.0206(12) -0.0016(10) 0.0067(10) -0.0046(11) C34 0.0345(14) 0.0271(13) 0.0195(11) -0.0001(10) 0.0057(10) -0.0014(10) C35 0.0449(16) 0.0223(13) 0.0278(13) 0.0001(10) 0.0033(11) -0.0067(11) C36 0.0334(14) 0.0334(14) 0.0264(12) -0.0052(11) 0.0046(10) -0.0087(11) C37 0.0322(14) 0.0297(13) 0.0201(11) -0.0029(10) 0.0081(10) -0.0023(11) C38 0.0385(15) 0.0231(12) 0.0322(13) 0.0020(10) 0.0035(11) -0.0013(11) C39 0.0337(14) 0.0275(13) 0.0293(13) 0.0019(10) 0.0015(10) -0.0063(11) C40 0.0314(14) 0.0386(15) 0.0282(13) 0.0017(11) 0.0054(10) -0.0021(11) C41 0.0362(15) 0.0354(15) 0.0454(15) 0.0005(12) 0.0063(12) 0.0025(11) C42 0.0353(16) 0.075(2) 0.0410(16) 0.0186(15) 0.0039(12) 0.0046(14) C43 0.0347(15) 0.0477(16) 0.0436(15) -0.0060(13) 0.0004(12) -0.0017(12) C44 0.0502(18) 0.0480(17) 0.0412(16) -0.0050(13) 0.0014(13) -0.0044(13) C45 0.0530(18) 0.0578(18) 0.0420(16) 0.0115(14) -0.0108(13) -0.0169(14) C46 0.0420(16) 0.0529(18) 0.0507(17) -0.0075(14) 0.0031(13) -0.0060(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si C45 1.854(3) . ? Si C44 1.859(3) . ? Si C46 1.865(3) . ? Si C2 1.871(2) . ? O C32 1.370(2) . ? O C33 1.372(3) . ? N1 C32 1.292(3) . ? N1 N2 1.411(2) . ? N2 C33 1.294(3) . ? C1 C10 1.383(3) . ? C1 C2 1.404(3) . ? C2 C3 1.399(3) . ? C3 C4 1.379(3) . ? C4 C11 1.395(3) . ? C5 C6 1.381(3) . ? C5 C12 1.388(3) . ? C6 C7 1.393(3) . ? C7 C8 1.398(3) . ? C7 C26 1.489(3) . ? C8 C13 1.379(3) . ? C9 C10 1.525(3) . ? C9 C13 1.525(3) . ? C9 C14 1.544(3) . ? C9 C20 1.547(3) . ? C10 C11 1.398(3) . ? C11 C12 1.465(3) . ? C12 C13 1.400(3) . ? C14 C15 1.526(3) . ? C15 C16 1.526(3) . ? C16 C17 1.515(3) . ? C17 C18 1.530(3) . ? C18 C19 1.504(4) . ? C20 C21 1.520(3) . ? C21 C22 1.526(3) . ? C22 C23 1.522(3) . ? C23 C24 1.518(3) . ? C24 C25 1.513(3) . ? C26 C27 1.395(3) . ? C26 C31 1.396(3) . ? C27 C28 1.380(3) . ? C28 C29 1.393(3) . ? C29 C30 1.392(3) . ? C29 C32 1.454(3) . ? C30 C31 1.374(3) . ? C33 C34 1.456(3) . ? C34 C35 1.386(3) . ? C34 C39 1.392(3) . ? C35 C36 1.375(3) . ? C36 C37 1.396(3) . ? C37 C38 1.400(3) . ? C37 C40 1.526(3) . ? C38 C39 1.381(3) . ? C40 C42 1.530(3) . ? C40 C41 1.535(3) . ? C40 C43 1.537(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 C45 Si C44 109.84(13) . . ? C45 Si C46 110.06(13) . . ? C44 Si C46 109.13(12) . . ? C45 Si C2 109.62(11) . . ? C44 Si C2 109.54(11) . . ? C46 Si C2 108.64(11) . . ? C32 O C33 102.66(16) . . ? C32 N1 N2 106.40(17) . . ? C33 N2 N1 106.41(18) . . ? C10 C1 C2 120.8(2) . . ? C3 C2 C1 117.6(2) . . ? C3 C2 Si 120.63(17) . . ? C1 C2 Si 121.80(16) . . ? C4 C3 C2 122.6(2) . . ? C3 C4 C11 118.7(2) . . ? C6 C5 C12 118.7(2) . . ? C5 C6 C7 122.0(2) . . ? C6 C7 C8 118.7(2) . . ? C6 C7 C26 120.33(19) . . ? C8 C7 C26 120.9(2) . . ? C13 C8 C7 120.0(2) . . ? C10 C9 C13 100.89(16) . . ? C10 C9 C14 113.11(18) . . ? C13 C9 C14 112.73(17) . . ? C10 C9 C20 110.41(17) . . ? C13 C9 C20 111.76(18) . . ? C14 C9 C20 107.90(17) . . ? C1 C10 C11 120.1(2) . . ? C1 C10 C9 128.49(19) . . ? C11 C10 C9 111.30(18) . . ? C4 C11 C10 120.2(2) . . ? C4 C11 C12 131.6(2) . . ? C10 C11 C12 108.16(19) . . ? C5 C12 C13 120.2(2) . . ? C5 C12 C11 131.0(2) . . ? C13 C12 C11 108.80(18) . . ? C8 C13 C12 120.42(19) . . ? C8 C13 C9 128.8(2) . . ? C12 C13 C9 110.79(18) . . ? C15 C14 C9 116.27(18) . . ? C16 C15 C14 112.21(19) . . ? C17 C16 C15 114.6(2) . . ? C16 C17 C18 113.5(2) . . ? C19 C18 C17 113.0(2) . . ? C21 C20 C9 115.87(18) . . ? C20 C21 C22 113.45(19) . . ? C23 C22 C21 115.0(2) . . ? C24 C23 C22 114.5(2) . . ? C25 C24 C23 113.9(2) . . ? C27 C26 C31 117.6(2) . . ? C27 C26 C7 122.63(19) . . ? C31 C26 C7 119.8(2) . . ? C28 C27 C26 120.9(2) . . ? C27 C28 C29 120.6(2) . . ? C30 C29 C28 119.0(2) . . ? C30 C29 C32 121.2(2) . . ? C28 C29 C32 119.8(2) . . ? C31 C30 C29 119.8(2) . . ? C30 C31 C26 122.1(2) . . ? N1 C32 O 112.34(19) . . ? N1 C32 C29 129.2(2) . . ? O C32 C29 118.38(19) . . ? N2 C33 O 112.18(19) . . ? N2 C33 C34 129.1(2) . . ? O C33 C34 118.73(19) . . ? C35 C34 C39 118.8(2) . . ? C35 C34 C33 119.4(2) . . ? C39 C34 C33 121.8(2) . . ? C36 C35 C34 120.9(2) . . ? C35 C36 C37 121.6(2) . . ? C36 C37 C38 116.7(2) . . ? C36 C37 C40 123.4(2) . . ? C38 C37 C40 119.9(2) . . ? C39 C38 C37 122.2(2) . . ? C38 C39 C34 119.8(2) . . ? C37 C40 C42 110.44(19) . . ? C37 C40 C41 108.44(18) . . ? C42 C40 C41 109.3(2) . . ? C37 C40 C43 111.88(19) . . ? C42 C40 C43 108.19(19) . . ? C41 C40 C43 108.50(19) . . ? 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 C45 Si C2 C1 8.2(2) . . . . ? C8 C7 C26 C27 37.7(3) . . . . ? C28 C29 C32 N1 -6.1(4) . . . . ? N2 C33 C34 C35 -6.7(4) . . . . ? C36 C37 C40 C43 5.6(3) . . . . ? C19 C18 C17 C16 -77.7(3) . . . . ? C18 C17 C16 C15 168.2(2) . . . . ? C17 C16 C15 C14 -72.7(3) . . . . ? C16 C15 C14 C9 -170.61(19) . . . . ? C15 C14 C9 C20 175.08(18) . . . . ? C14 C9 C20 C21 -173.81(19) . . . . ? C9 C20 C21 C22 164.89(19) . . . . ? C20 C21 C22 C23 -63.1(3) . . . . ? C21 C22 C23 C24 -175.7(2) . . . . ? C22 C23 C24 C25 179.2(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.359 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.042 #===================================END data_(13) _database_code_depnum_ccdc_archive 'CCDC 602977' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(4-tert-Butylphenyl)-5-[4-(9,9-dihexyl-2-bromofluoren-7- yl)phenyl]-1,3,4-oxadiazole ; _chemical_name_common ; 2-(4-tert-Butylphenyl)-5-(4-(9,9-dihexyl-2-bromofluoren-7- yl)phenyl)-1,3,4-oxadiazole ; _chemical_melting_point 407.6(5) _chemical_formula_moiety 'C43 H49 Br N2 O' _chemical_formula_sum 'C43 H49 Br N2 O' _chemical_formula_weight 689.75 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' Br Br -0.2901 2.4595 '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 10.945(5) _cell_length_b 12.714(3) _cell_length_c 13.128(4) _cell_angle_alpha 96.10(1) _cell_angle_beta 93.84(1) _cell_angle_gamma 94.38(1) _cell_volume 1806.0(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 993 _cell_measurement_theta_min 12.08 _cell_measurement_theta_max 23.26 _exptl_crystal_description trapetsoid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 1.174 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7113 _exptl_absorpt_correction_T_max 0.8594 _exptl_absorpt_process_details 'XPREP v.6.12 (Bruker,2001), R(int)=0.061 before correction' 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 0.00 0.1500 0.00 1.00 0.00 0.1500 -1.00 0.00 -1.00 0.0800 0.00 0.00 -1.00 0.0700 0.00 0.00 1.00 0.0800 3.00 1.00 0.00 0.1600 _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 (5 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.85 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 'Bruker SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_reflns_number 32533 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 30.00 _reflns_number_total 10531 _reflns_number_gt 7932 _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 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _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. Atoms C(19), C(40), C(41), C(42) and C(43) (with their H) are disordered between positions A and B, occupancies 82.0(2)% and 18.0(2)%, respectively. all C(40)---C(Me) bond lengths were restrained to similarity. The ordered methyl group C(25)H~3~ was refined as rigid body, other H atoms were included in riding mode. ; _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^)+(0.0505P)^2^] 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 10531 _refine_ls_number_parameters 447 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.033 _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 Br Br 0.702749(15) -0.039572(12) 0.137215(14) 0.03994(6) Uani 1 1 d . . . O O -0.06775(9) 0.84734(7) 0.53665(7) 0.0226(2) Uani 1 1 d . . . N1 N -0.17002(11) 0.77223(10) 0.39288(10) 0.0294(3) Uani 1 1 d . . . N2 N -0.23040(12) 0.86014(10) 0.43066(10) 0.0310(3) Uani 1 1 d . . . C1 C 0.53812(12) 0.12176(10) 0.16824(11) 0.0220(3) Uani 1 1 d . . . H1 H 0.5213 0.1111 0.0958 0.026 Uiso 1 1 d R . . C2 C 0.62136(13) 0.06296(11) 0.21778(12) 0.0260(3) Uani 1 1 d . . . C3 C 0.64797(13) 0.07673(11) 0.32330(12) 0.0274(3) Uani 1 1 d . . . H3 H 0.7050 0.0350 0.3546 0.033 Uiso 1 1 d R . . C4 C 0.58989(13) 0.15195(11) 0.38280(11) 0.0242(3) Uani 1 1 d . . . H4 H 0.6077 0.1629 0.4551 0.029 Uiso 1 1 d R . . C5 C 0.42013(13) 0.33854(11) 0.47838(10) 0.0241(3) Uani 1 1 d . . . H5 H 0.4684 0.3167 0.5339 0.029 Uiso 1 1 d R . . C6 C 0.33924(13) 0.41627(11) 0.49585(10) 0.0240(3) Uani 1 1 d . . . H6 H 0.3332 0.4480 0.5640 0.029 Uiso 1 1 d R . . C7 C 0.26608(12) 0.44898(10) 0.41523(10) 0.0202(3) Uani 1 1 d . . . C8 C 0.27694(11) 0.40225(10) 0.31458(10) 0.0188(2) Uani 1 1 d . . . H8 H 0.2284 0.4235 0.2588 0.023 Uiso 1 1 d R . . C9 C 0.38870(11) 0.27161(10) 0.19392(9) 0.0171(2) Uani 1 1 d . . . C10 C 0.48084(11) 0.19633(10) 0.22860(10) 0.0184(2) Uani 1 1 d . . . C11 C 0.50579(11) 0.21135(10) 0.33545(10) 0.0196(3) Uani 1 1 d . . . C12 C 0.42955(11) 0.29302(10) 0.37806(10) 0.0190(2) Uani 1 1 d . . . C13 C 0.35801(11) 0.32574(10) 0.29685(10) 0.0172(2) Uani 1 1 d . . . C14 C 0.45004(11) 0.35442(10) 0.13047(10) 0.0190(2) Uani 1 1 d . . . H141 H 0.4806 0.3161 0.0689 0.025 Uiso 1 1 d R . . H142 H 0.3866 0.3994 0.1064 0.025 Uiso 1 1 d R . . C15 C 0.55617(12) 0.42642(10) 0.18740(10) 0.0216(3) Uani 1 1 d . . . H151 H 0.5243 0.4713 0.2443 0.028 Uiso 1 1 d R . . H152 H 0.6161 0.3819 0.2179 0.028 Uiso 1 1 d R . . C16 C 0.62183(12) 0.49763(11) 0.11854(11) 0.0235(3) Uani 1 1 d . . . H161 H 0.5620 0.5416 0.0873 0.031 Uiso 1 1 d R . . H162 H 0.6552 0.4530 0.0623 0.031 Uiso 1 1 d R . . C17 C 0.72614(14) 0.56983(12) 0.17749(12) 0.0328(3) Uani 1 1 d . A . H171 H 0.6915 0.6147 0.2329 0.043 Uiso 1 1 d R . . H172 H 0.7838 0.5251 0.2105 0.043 Uiso 1 1 d R . . C18 C 0.79852(16) 0.64104(14) 0.11364(15) 0.0430(4) Uani 1 1 d . . . H18 H 0.7447 0.6838 0.0786 0.056 Uiso 1 1 d R A . H18A H 0.8548 0.6879 0.1599 0.052 Uiso 0.820(2) 1 d PR A 1 H18B H 0.8271 0.5937 0.0602 0.052 Uiso 0.180(2) 1 d PR A 2 C19A C 0.8732(2) 0.57888(19) 0.0410(2) 0.0497(6) Uani 0.820(2) 1 d P A 1 H191 H 0.9189 0.6273 0.0011 0.075 Uiso 0.820(2) 1 d PR A 1 H192 H 0.8181 0.5284 -0.0056 0.075 Uiso 0.820(2) 1 d PR A 1 H193 H 0.9311 0.5401 0.0798 0.075 Uiso 0.820(2) 1 d PR A 1 C19B C 0.9001(9) 0.7085(7) 0.1429(8) 0.039(2) Uiso 0.180(2) 1 d P A 2 H194 H 0.9289 0.7442 0.0853 0.059 Uiso 0.180(2) 1 d PR A 2 H195 H 0.9660 0.6698 0.1713 0.059 Uiso 0.180(2) 1 d PR A 2 H196 H 0.8767 0.7615 0.1962 0.059 Uiso 0.180(2) 1 d PR A 2 C20 C 0.27542(11) 0.21442(10) 0.12996(10) 0.0188(2) Uani 1 1 d . . . H201 H 0.2174 0.2679 0.1152 0.024 Uiso 1 1 d R . . H202 H 0.3019 0.1836 0.0634 0.024 Uiso 1 1 d R . . C21 C 0.20676(12) 0.12671(10) 0.17918(10) 0.0218(3) Uani 1 1 d . . . H211 H 0.1869 0.1550 0.2487 0.028 Uiso 1 1 d R . . H212 H 0.2609 0.0687 0.1867 0.028 Uiso 1 1 d R . . C22 C 0.08798(12) 0.08164(11) 0.11622(11) 0.0250(3) Uani 1 1 d . . . H221 H 0.1087 0.0533 0.0469 0.033 Uiso 1 1 d R . . H222 H 0.0514 0.0215 0.1492 0.033 Uiso 1 1 d R . . C23 C -0.00851(13) 0.16139(11) 0.10457(11) 0.0268(3) Uani 1 1 d . . . H231 H 0.0255 0.2186 0.0664 0.035 Uiso 1 1 d R . . H232 H -0.0813 0.1250 0.0629 0.035 Uiso 1 1 d R . . C24 C -0.04958(14) 0.21134(13) 0.20583(13) 0.0335(3) Uani 1 1 d . . . H241 H -0.0821 0.1545 0.2451 0.043 Uiso 1 1 d R . . H242 H 0.0223 0.2501 0.2469 0.043 Uiso 1 1 d R . . C25 C -0.14816(16) 0.28779(14) 0.18987(15) 0.0429(4) Uani 1 1 d . . . H251 H -0.1162 0.3445 0.1513 0.057(3) Uiso 1 1 d R . . H252 H -0.1711 0.3188 0.2567 0.057(3) Uiso 1 1 d R . . H253 H -0.2206 0.2492 0.1512 0.057(3) Uiso 1 1 d R . . C26 C 0.17810(12) 0.53063(10) 0.43236(10) 0.0210(3) Uani 1 1 d . . . C27 C 0.20526(12) 0.62128(11) 0.50255(11) 0.0242(3) Uani 1 1 d . . . H27 H 0.2808 0.6296 0.5437 0.029 Uiso 1 1 d R . . C28 C 0.12322(13) 0.69947(11) 0.51307(11) 0.0248(3) Uani 1 1 d . . . H28 H 0.1430 0.7607 0.5611 0.030 Uiso 1 1 d R . . C29 C 0.01249(12) 0.68798(10) 0.45325(10) 0.0218(3) Uani 1 1 d . . . C30 C -0.01693(13) 0.59617(11) 0.38490(11) 0.0250(3) Uani 1 1 d . . . H30 H -0.0936 0.5868 0.3453 0.030 Uiso 1 1 d R . . C31 C 0.06484(12) 0.51942(11) 0.37489(10) 0.0238(3) Uani 1 1 d . . . H31 H 0.0438 0.4575 0.3279 0.029 Uiso 1 1 d R . . C32 C -0.07638(12) 0.76769(10) 0.45730(10) 0.0224(3) Uani 1 1 d . . . C33 C -0.16806(13) 0.90083(10) 0.51418(11) 0.0238(3) Uani 1 1 d . . . C34 C -0.19670(13) 0.99026(10) 0.58529(11) 0.0243(3) Uani 1 1 d . A . C35 C -0.10636(15) 1.05282(11) 0.64891(11) 0.0286(3) Uani 1 1 d . . . H35 H -0.0226 1.0392 0.6451 0.034 Uiso 1 1 d R . . C36 C -0.13822(16) 1.13494(12) 0.71780(12) 0.0328(3) Uani 1 1 d . A . H36 H -0.0754 1.1778 0.7598 0.039 Uiso 1 1 d R . . C37 C -0.26044(16) 1.15547(11) 0.72666(12) 0.0329(4) Uani 1 1 d D . . C38 C -0.34952(15) 1.09244(12) 0.66191(12) 0.0332(3) Uani 1 1 d . A . H38 H -0.4334 1.1056 0.6659 0.040 Uiso 1 1 d R . . C39 C -0.31897(14) 1.01111(12) 0.59173(12) 0.0289(3) Uani 1 1 d . . . H39 H -0.3814 0.9697 0.5481 0.035 Uiso 1 1 d R A . C40A C -0.2923(2) 1.24149(16) 0.80949(16) 0.0296(5) Uani 0.820(2) 1 d PD A 1 C41A C -0.3835(2) 1.31060(18) 0.76057(18) 0.0522(7) Uani 0.820(2) 1 d PD A 1 H411 H -0.3437 1.3443 0.7062 0.078 Uiso 0.820(2) 1 d PR A 1 H412 H -0.4043 1.3654 0.8133 0.078 Uiso 0.820(2) 1 d PR A 1 H413 H -0.4586 1.2683 0.7312 0.078 Uiso 0.820(2) 1 d PR A 1 C42A C -0.3512(2) 1.18461(18) 0.89365(16) 0.0406(5) Uani 0.820(2) 1 d PD A 1 H421 H -0.2905 1.1402 0.9212 0.061 Uiso 0.820(2) 1 d PR A 1 H422 H -0.4258 1.1401 0.8669 0.061 Uiso 0.820(2) 1 d PR A 1 H423 H -0.3712 1.2377 0.9484 0.061 Uiso 0.820(2) 1 d PR A 1 C43A C -0.1817(2) 1.31433(17) 0.85875(18) 0.0485(6) Uani 0.820(2) 1 d PD A 1 H431 H -0.1231 1.2708 0.8905 0.073 Uiso 0.820(2) 1 d PR A 1 H432 H -0.2078 1.3668 0.9113 0.073 Uiso 0.820(2) 1 d PR A 1 H433 H -0.1424 1.3510 0.8060 0.073 Uiso 0.820(2) 1 d PR A 1 C40B C -0.3372(7) 1.2343(7) 0.7947(7) 0.022(2) Uiso 0.180(2) 1 d PD A 2 C41B C -0.2884(11) 1.2095(10) 0.9017(8) 0.056(3) Uiso 0.180(2) 1 d PD A 2 H414 H -0.3068 1.1324 0.8967 0.084 Uiso 0.180(2) 1 d PR A 2 H415 H -0.3475 1.2446 0.9437 0.084 Uiso 0.180(2) 1 d PR A 2 H416 H -0.2051 1.2284 0.9337 0.084 Uiso 0.180(2) 1 d PR A 2 C42B C -0.2771(9) 1.3433(7) 0.7797(8) 0.048(3) Uiso 0.180(2) 1 d PD A 2 H424 H -0.2790 1.3399 0.7047 0.072 Uiso 0.180(2) 1 d PR A 2 H425 H -0.1971 1.3759 0.8100 0.072 Uiso 0.180(2) 1 d PR A 2 H426 H -0.3421 1.3860 0.8046 0.072 Uiso 0.180(2) 1 d PR A 2 C43B C -0.4748(7) 1.2365(8) 0.7911(8) 0.042(2) Uiso 0.180(2) 1 d PD A 2 H434 H -0.5115 1.1686 0.8085 0.063 Uiso 0.180(2) 1 d PR A 2 H435 H -0.5001 1.2448 0.7196 0.063 Uiso 0.180(2) 1 d PR A 2 H436 H -0.5026 1.2947 0.8365 0.063 Uiso 0.180(2) 1 d PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.03863(10) 0.03322(9) 0.04841(11) -0.00703(7) 0.00693(7) 0.01892(7) O 0.0264(5) 0.0198(4) 0.0221(5) -0.0002(4) 0.0045(4) 0.0068(4) N1 0.0330(7) 0.0268(6) 0.0284(7) -0.0022(5) -0.0019(5) 0.0138(5) N2 0.0365(7) 0.0268(6) 0.0308(7) -0.0007(5) 0.0007(5) 0.0157(5) C1 0.0221(6) 0.0207(6) 0.0232(7) -0.0001(5) 0.0034(5) 0.0036(5) C2 0.0245(7) 0.0194(6) 0.0343(8) -0.0011(5) 0.0051(6) 0.0059(5) C3 0.0245(7) 0.0232(7) 0.0353(8) 0.0049(6) -0.0017(6) 0.0087(5) C4 0.0240(7) 0.0246(7) 0.0244(7) 0.0038(5) -0.0020(5) 0.0056(5) C5 0.0264(7) 0.0279(7) 0.0180(6) 0.0018(5) -0.0019(5) 0.0070(5) C6 0.0261(7) 0.0285(7) 0.0171(6) -0.0016(5) 0.0015(5) 0.0053(5) C7 0.0189(6) 0.0204(6) 0.0207(6) -0.0013(5) 0.0016(5) 0.0031(5) C8 0.0182(6) 0.0202(6) 0.0178(6) 0.0010(5) -0.0007(5) 0.0036(5) C9 0.0169(6) 0.0175(6) 0.0168(6) 0.0007(5) 0.0008(4) 0.0032(5) C10 0.0170(6) 0.0168(6) 0.0212(6) 0.0015(5) 0.0015(5) 0.0016(5) C11 0.0182(6) 0.0181(6) 0.0226(7) 0.0021(5) 0.0011(5) 0.0029(5) C12 0.0186(6) 0.0188(6) 0.0198(6) 0.0024(5) 0.0009(5) 0.0033(5) C13 0.0177(6) 0.0165(6) 0.0171(6) 0.0009(4) 0.0014(5) 0.0011(4) C14 0.0188(6) 0.0199(6) 0.0183(6) 0.0017(5) 0.0015(5) 0.0022(5) C15 0.0201(6) 0.0227(6) 0.0214(6) 0.0034(5) -0.0024(5) 0.0006(5) C16 0.0219(6) 0.0240(7) 0.0238(7) 0.0035(5) -0.0009(5) -0.0007(5) C17 0.0296(8) 0.0295(8) 0.0371(9) 0.0085(6) -0.0103(6) -0.0074(6) C18 0.0371(9) 0.0334(9) 0.0568(11) 0.0100(8) 0.0004(8) -0.0122(7) C19A 0.0330(11) 0.0493(13) 0.0696(17) 0.0227(12) 0.0106(11) -0.0067(10) C20 0.0188(6) 0.0196(6) 0.0175(6) -0.0001(5) 0.0005(5) 0.0017(5) C21 0.0218(6) 0.0195(6) 0.0241(7) 0.0040(5) 0.0002(5) 0.0009(5) C22 0.0231(7) 0.0216(6) 0.0292(7) 0.0006(5) 0.0011(5) -0.0013(5) C23 0.0204(7) 0.0287(7) 0.0304(8) 0.0038(6) -0.0025(5) -0.0006(5) C24 0.0263(7) 0.0369(8) 0.0360(9) -0.0017(7) -0.0023(6) 0.0071(6) C25 0.0317(9) 0.0437(10) 0.0528(11) -0.0020(8) 0.0008(8) 0.0130(7) C26 0.0218(6) 0.0219(6) 0.0193(6) -0.0003(5) 0.0034(5) 0.0049(5) C27 0.0202(6) 0.0273(7) 0.0236(7) -0.0044(5) -0.0012(5) 0.0050(5) C28 0.0253(7) 0.0229(6) 0.0247(7) -0.0059(5) 0.0018(5) 0.0039(5) C29 0.0236(6) 0.0211(6) 0.0212(7) 0.0006(5) 0.0043(5) 0.0057(5) C30 0.0231(7) 0.0273(7) 0.0235(7) -0.0028(5) -0.0021(5) 0.0057(5) C31 0.0246(7) 0.0236(7) 0.0217(7) -0.0053(5) 0.0001(5) 0.0048(5) C32 0.0263(7) 0.0199(6) 0.0210(6) -0.0003(5) 0.0038(5) 0.0043(5) C33 0.0282(7) 0.0212(6) 0.0242(7) 0.0055(5) 0.0065(5) 0.0078(5) C34 0.0335(7) 0.0189(6) 0.0233(7) 0.0058(5) 0.0106(6) 0.0077(5) C35 0.0358(8) 0.0231(7) 0.0285(7) 0.0036(6) 0.0110(6) 0.0037(6) C36 0.0491(9) 0.0223(7) 0.0280(8) 0.0025(6) 0.0110(7) 0.0026(6) C37 0.0571(10) 0.0207(7) 0.0250(7) 0.0069(6) 0.0176(7) 0.0113(7) C38 0.0418(9) 0.0305(8) 0.0331(8) 0.0112(6) 0.0166(7) 0.0170(7) C39 0.0342(8) 0.0260(7) 0.0297(8) 0.0076(6) 0.0090(6) 0.0104(6) C40A 0.0369(13) 0.0264(10) 0.0269(11) -0.0006(7) 0.0101(10) 0.0101(9) C41A 0.0736(18) 0.0391(12) 0.0471(14) -0.0030(10) 0.0091(12) 0.0325(12) C42A 0.0515(14) 0.0415(12) 0.0299(11) -0.0017(9) 0.0207(10) 0.0044(11) C43A 0.0584(15) 0.0355(11) 0.0484(14) -0.0160(10) 0.0211(11) -0.0022(10) _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 Br C2 1.9031(14) . ? O C32 1.3667(16) . ? O C33 1.3668(16) . ? N1 C32 1.2932(19) . ? N1 N2 1.4040(16) . ? N2 C33 1.2886(19) . ? C1 C10 1.3847(18) . ? C1 C2 1.3929(19) . ? C2 C3 1.386(2) . ? C3 C4 1.3890(19) . ? C4 C11 1.3904(18) . ? C5 C6 1.3877(19) . ? C5 C12 1.3947(18) . ? C6 C7 1.4018(19) . ? C7 C8 1.4064(18) . ? C7 C26 1.4792(18) . ? C8 C13 1.3781(17) . ? C9 C13 1.5201(17) . ? C9 C10 1.5228(17) . ? C9 C20 1.5376(18) . ? C9 C14 1.5513(18) . ? C10 C11 1.4009(19) . ? C11 C12 1.4693(17) . ? C12 C13 1.3983(18) . ? C14 C15 1.5237(18) . ? C15 C16 1.5215(19) . ? C16 C17 1.5217(19) . ? C17 C18 1.513(2) . ? C18 C19B 1.359(9) . ? C18 C19A 1.498(3) . ? C20 C21 1.5218(18) . ? C21 C22 1.5309(19) . ? C22 C23 1.530(2) . ? C23 C24 1.522(2) . ? C24 C25 1.525(2) . ? C26 C27 1.3967(18) . ? C26 C31 1.3968(19) . ? C27 C28 1.3918(19) . ? C28 C29 1.389(2) . ? C29 C30 1.3974(19) . ? C29 C32 1.4567(18) . ? C30 C31 1.3756(19) . ? C33 C34 1.4597(19) . ? C34 C39 1.390(2) . ? C34 C35 1.391(2) . ? C35 C36 1.388(2) . ? C36 C37 1.392(2) . ? C37 C38 1.393(2) . ? C37 C40A 1.535(2) . ? C37 C40B 1.596(9) . ? C38 C39 1.386(2) . ? C40A C43A 1.529(3) . ? C40A C41A 1.532(3) . ? C40A C42A 1.534(3) . ? C40B C43B 1.506(10) . ? C40B C42B 1.527(10) . ? C40B C41B 1.541(11) . ? 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 C32 O C33 102.13(10) . . ? C32 N1 N2 106.21(11) . . ? C33 N2 N1 106.29(11) . . ? C10 C1 C2 117.48(13) . . ? C3 C2 C1 122.61(12) . . ? C3 C2 Br 118.72(10) . . ? C1 C2 Br 118.67(11) . . ? C2 C3 C4 119.23(13) . . ? C3 C4 C11 119.40(13) . . ? C6 C5 C12 119.04(12) . . ? C5 C6 C7 121.49(12) . . ? C6 C7 C8 118.65(12) . . ? C6 C7 C26 122.35(12) . . ? C8 C7 C26 119.00(12) . . ? C13 C8 C7 120.00(12) . . ? C13 C9 C10 100.88(10) . . ? C13 C9 C20 112.99(10) . . ? C10 C9 C20 113.33(10) . . ? C13 C9 C14 109.95(10) . . ? C10 C9 C14 110.87(10) . . ? C20 C9 C14 108.66(10) . . ? C1 C10 C11 120.96(12) . . ? C1 C10 C9 127.97(12) . . ? C11 C10 C9 111.06(11) . . ? C4 C11 C10 120.32(12) . . ? C4 C11 C12 131.33(12) . . ? C10 C11 C12 108.34(11) . . ? C5 C12 C13 120.02(12) . . ? C5 C12 C11 131.82(12) . . ? C13 C12 C11 108.16(11) . . ? C8 C13 C12 120.79(12) . . ? C8 C13 C9 127.75(12) . . ? C12 C13 C9 111.37(11) . . ? C15 C14 C9 115.27(11) . . ? C16 C15 C14 113.05(11) . . ? C15 C16 C17 112.03(12) . . ? C18 C17 C16 115.26(14) . . ? C19B C18 C19A 88.7(4) . . ? C19B C18 C17 128.8(4) . . ? C19A C18 C17 111.75(15) . . ? C21 C20 C9 115.69(11) . . ? C20 C21 C22 112.57(11) . . ? C23 C22 C21 114.75(11) . . ? C24 C23 C22 114.28(12) . . ? C23 C24 C25 112.17(14) . . ? C27 C26 C31 118.06(12) . . ? C27 C26 C7 122.31(12) . . ? C31 C26 C7 119.60(12) . . ? C28 C27 C26 120.99(13) . . ? C29 C28 C27 119.98(13) . . ? C28 C29 C30 119.41(12) . . ? C28 C29 C32 123.30(12) . . ? C30 C29 C32 117.29(12) . . ? C31 C30 C29 120.18(13) . . ? C30 C31 C26 121.35(13) . . ? N1 C32 O 112.59(12) . . ? N1 C32 C29 126.99(12) . . ? O C32 C29 120.40(12) . . ? N2 C33 O 112.77(12) . . ? N2 C33 C34 127.60(13) . . ? O C33 C34 119.55(12) . . ? C39 C34 C35 119.14(13) . . ? C39 C34 C33 118.59(14) . . ? C35 C34 C33 122.23(13) . . ? C36 C35 C34 120.28(15) . . ? C35 C36 C37 121.28(16) . . ? C36 C37 C38 117.61(14) . . ? C36 C37 C40A 119.55(17) . . ? C38 C37 C40A 122.78(17) . . ? C36 C37 C40B 138.2(3) . . ? C38 C37 C40B 104.1(3) . . ? C40A C37 C40B 18.7(3) . . ? C39 C38 C37 121.76(15) . . ? C38 C39 C34 119.91(15) . . ? C43A C40A C41A 107.96(19) . . ? C43A C40A C42A 108.49(19) . . ? C41A C40A C42A 110.4(2) . . ? C43A C40A C37 114.17(18) . . ? C41A C40A C37 108.55(18) . . ? C42A C40A C37 107.24(16) . . ? C43B C40B C42B 110.2(7) . . ? C43B C40B C41B 109.7(8) . . ? C42B C40B C41B 106.6(8) . . ? C43B C40B C37 127.3(7) . . ? C42B C40B C37 102.7(7) . . ? C41B C40B C37 98.4(7) . . ? 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 C19A C18 C17 C16 -68.9(2) . . . . ? C18 C17 C16 C15 178.31(14) . . . . ? C17 C16 C15 C14 179.16(12) . . . . ? C16 C15 C14 C9 173.68(11) . . . . ? C15 C14 C9 C20 173.77(10) . . . . ? C14 C9 C20 C21 177.57(10) . . . . ? C9 C20 C21 C22 173.98(11) . . . . ? C20 C21 C22 C23 -62.83(16) . . . . ? C21 C22 C23 C24 -58.47(17) . . . . ? C22 C23 C24 C25 -178.44(13) . . . . ? C19B C18 C17 C16 -175.7(5) . . . . ? C6 C7 C26 C27 39.8(2) . . . . ? C28 C29 C32 O -14.8(2) . . . . ? O C33 C34 C35 28.4(2) . . . . ? C36 C37 C40A C43A 13.5(2) . . . . ? C36 C37 C40B C43B -177.1(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.517 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.053 #=====================================END data_(20) _database_code_depnum_ccdc_archive 'CCDC 602978' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-Bis[2-(4-diphenylaminophenyl)-1,3,4-oxadiazol-5- yl]pyridine, deuterochloroform trisolvate ; _chemical_name_common ; 2,5-Bis(2-(4-diphenylaminophenyl)-1,3,4-oxadiazol-5- yl)pyridine, deuterochloroform trisolvate ; _chemical_melting_point 543.1(4) _chemical_formula_moiety 'C45 H31 N7 O2,3(C D Cl3)' _chemical_formula_sum 'C48 H31 Cl9 D3 N7 O2' _chemical_formula_weight 1062.89 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' D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 21.462(6) _cell_length_b 9.581(3) _cell_length_c 23.428(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.48(2) _cell_angle_gamma 90.00 _cell_volume 4787(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 999 _cell_measurement_theta_min 12.08 _cell_measurement_theta_max 22.75 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2160 _exptl_absorpt_coefficient_mu 0.575 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7895 _exptl_absorpt_correction_T_max 0.9352 _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 0.00 1.00 0.0800 0.00 0.00 -1.00 0.0800 1.00 0.00 0.00 0.0600 -1.00 0.00 0.00 0.0600 0.00 -1.00 0.00 0.3000 0.00 1.00 0.00 0.3000 _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 (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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 21479 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4224 _reflns_number_gt 3572 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.049 (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. H(3) - refall, other H atoms - "riding" (constr). ; _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^)+(0.0644P)^2^+1.5036P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4224 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1656 _refine_ls_wR_factor_gt 0.1607 _refine_ls_goodness_of_fit_ref 1.681 _refine_ls_restrained_S_all 1.681 _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 O O 0.51344(8) 0.35916(19) 0.44422(7) 0.0257(4) Uani 1 1 d . . . N2 N 0.59864(12) 0.3206(3) 0.50447(10) 0.0357(6) Uani 1 1 d . . . N3 N 0.60103(11) 0.4573(3) 0.48355(10) 0.0347(6) Uani 1 1 d . . . N4 N 0.48716(10) 0.9629(2) 0.31782(10) 0.0283(5) Uani 1 1 d . . . C1 C 0.56036(13) 0.0372(3) 0.52279(11) 0.0327(6) Uani 0.50 1 d P . 1 H1 H 0.6023 0.0621 0.5386 0.039 Uiso 0.50 1 d PR . 1 N1 N 0.56036(13) 0.0372(3) 0.52279(11) 0.0327(6) Uani 0.50 1 d P . 2 C2 C 0.52231(13) 0.1290(3) 0.48925(11) 0.0291(6) Uani 1 1 d . . . C3 C 0.46261(14) 0.0900(3) 0.46645(12) 0.0303(6) Uani 1 1 d . . . H3 H 0.4346(16) 0.149(3) 0.4484(14) 0.041(9) Uiso 1 1 d . . . C4 C 0.54722(13) 0.2675(3) 0.48062(11) 0.0277(6) Uani 1 1 d . . . C5 C 0.55084(12) 0.4755(3) 0.44804(11) 0.0266(6) Uani 1 1 d . . . C11 C 0.53279(12) 0.5980(3) 0.41417(11) 0.0253(6) Uani 1 1 d . . . C12 C 0.47883(12) 0.6022(3) 0.37432(11) 0.0264(6) Uani 1 1 d . . . H12 H 0.4524 0.5227 0.3692 0.032 Uiso 1 1 d R . . C13 C 0.46403(12) 0.7213(3) 0.34243(11) 0.0266(6) Uani 1 1 d . . . H13 H 0.4277 0.7225 0.3154 0.032 Uiso 1 1 d R . . C14 C 0.50213(12) 0.8405(3) 0.34975(11) 0.0249(6) Uani 1 1 d . . . C15 C 0.55615(12) 0.8350(3) 0.38903(12) 0.0270(6) Uani 1 1 d . . . H15 H 0.5827 0.9142 0.3942 0.032 Uiso 1 1 d R . . C16 C 0.57143(12) 0.7162(3) 0.42032(11) 0.0277(6) Uani 1 1 d . . . H16 H 0.6086 0.7138 0.4463 0.033 Uiso 1 1 d R . . C21 C 0.53758(12) 1.0566(3) 0.30919(12) 0.0261(6) Uani 1 1 d . . . C22 C 0.58856(13) 1.0079(3) 0.28365(13) 0.0327(7) Uani 1 1 d . . . H22 H 0.5889 0.9155 0.2692 0.039 Uiso 1 1 d R . . C23 C 0.63894(13) 1.0955(4) 0.27928(13) 0.0399(8) Uani 1 1 d . . . H23 H 0.6746 1.0616 0.2632 0.048 Uiso 1 1 d R . . C24 C 0.63810(14) 1.2328(4) 0.29871(13) 0.0403(8) Uani 1 1 d . . . H24 H 0.6728 1.2924 0.2955 0.048 Uiso 1 1 d R . . C25 C 0.58634(15) 1.2812(3) 0.32259(12) 0.0372(7) Uani 1 1 d . . . H25 H 0.5851 1.3750 0.3353 0.045 Uiso 1 1 d R . . C26 C 0.53624(13) 1.1934(3) 0.32766(12) 0.0309(6) Uani 1 1 d . . . H26 H 0.5007 1.2272 0.3440 0.037 Uiso 1 1 d R . . C31 C 0.42468(12) 1.0055(3) 0.29946(12) 0.0268(6) Uani 1 1 d . . . C32 C 0.41201(13) 1.0850(3) 0.24994(12) 0.0299(6) Uani 1 1 d . . . H32 H 0.4452 1.1105 0.2285 0.036 Uiso 1 1 d R . . C33 C 0.35109(13) 1.1267(3) 0.23130(13) 0.0339(7) Uani 1 1 d . . . H33 H 0.3429 1.1821 0.1977 0.041 Uiso 1 1 d R . . C34 C 0.30214(13) 1.0883(3) 0.26209(14) 0.0356(7) Uani 1 1 d . . . H34 H 0.2604 1.1151 0.2492 0.043 Uiso 1 1 d R . . C35 C 0.31453(13) 1.0108(3) 0.31153(14) 0.0361(7) Uani 1 1 d . . . H35 H 0.2811 0.9849 0.3326 0.043 Uiso 1 1 d R . . C36 C 0.37519(13) 0.9699(3) 0.33094(13) 0.0316(6) Uani 1 1 d . . . H36 H 0.3831 0.9177 0.3654 0.038 Uiso 1 1 d R . . Cl1 Cl 0.69876(4) 0.35401(10) 0.64017(4) 0.0519(3) Uani 1 1 d . . . Cl2 Cl 0.78068(4) 0.51904(11) 0.57848(4) 0.0581(3) Uani 1 1 d . . . Cl3 Cl 0.67678(6) 0.64912(12) 0.62809(5) 0.0731(4) Uani 1 1 d . . . C6 C 0.70378(15) 0.4990(4) 0.59504(14) 0.0436(8) Uani 1 1 d . . . D6 D 0.6760 0.4821 0.5586 0.052 Uiso 1 1 d R . . Cl4 Cl 0.69408(11) 0.0783(3) 0.42999(8) 0.0673(6) Uani 0.50 1 d P A -1 Cl5 Cl 0.71774(13) -0.1090(3) 0.52507(13) 0.0964(9) Uani 0.50 1 d P A -1 Cl6 Cl 0.77975(12) 0.1546(3) 0.52482(18) 0.1137(13) Uani 0.50 1 d P A -1 C7 C 0.7119(3) 0.0646(9) 0.5043(3) 0.0549(18) Uani 0.50 1 d P A -1 D7 D 0.6772 0.1086 0.5229 0.066 Uiso 0.50 1 d PR A -1 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 O 0.0292(10) 0.0250(10) 0.0228(9) 0.0020(7) 0.0026(7) 0.0017(8) N2 0.0373(14) 0.0391(15) 0.0297(13) 0.0076(11) -0.0012(11) 0.0018(11) N3 0.0333(13) 0.0366(14) 0.0331(13) 0.0050(11) -0.0008(10) -0.0021(11) N4 0.0223(11) 0.0222(12) 0.0403(14) 0.0025(10) 0.0029(10) -0.0005(9) C1 0.0402(15) 0.0342(15) 0.0237(13) 0.0066(11) 0.0039(11) 0.0062(12) N1 0.0402(15) 0.0342(15) 0.0237(13) 0.0066(11) 0.0039(11) 0.0062(12) C2 0.0369(15) 0.0323(16) 0.0189(13) 0.0061(11) 0.0069(11) 0.0077(12) C3 0.0382(16) 0.0294(16) 0.0232(14) 0.0085(12) 0.0028(12) 0.0088(13) C4 0.0309(14) 0.0337(16) 0.0188(13) 0.0034(11) 0.0045(11) 0.0058(12) C5 0.0275(14) 0.0301(15) 0.0230(13) -0.0018(11) 0.0062(11) -0.0004(11) C11 0.0255(13) 0.0265(14) 0.0244(13) -0.0015(11) 0.0056(11) 0.0019(11) C12 0.0257(13) 0.0230(14) 0.0313(14) -0.0034(11) 0.0067(11) -0.0025(11) C13 0.0220(13) 0.0270(14) 0.0305(14) -0.0015(12) 0.0013(11) 0.0003(11) C14 0.0242(13) 0.0233(14) 0.0278(14) -0.0021(11) 0.0058(11) 0.0018(10) C15 0.0260(14) 0.0237(14) 0.0320(15) -0.0042(11) 0.0061(11) -0.0029(11) C16 0.0257(14) 0.0300(15) 0.0269(14) -0.0048(11) 0.0005(11) 0.0002(11) C21 0.0210(13) 0.0252(14) 0.0318(14) 0.0010(11) 0.0014(11) -0.0010(11) C22 0.0282(15) 0.0315(16) 0.0385(16) 0.0056(13) 0.0041(12) 0.0068(12) C23 0.0243(14) 0.052(2) 0.0441(18) 0.0176(15) 0.0065(13) 0.0059(13) C24 0.0318(16) 0.0463(19) 0.0406(17) 0.0152(15) -0.0059(13) -0.0152(14) C25 0.0471(18) 0.0319(17) 0.0317(16) 0.0009(13) 0.0001(13) -0.0128(14) C26 0.0327(15) 0.0290(15) 0.0313(15) -0.0014(12) 0.0044(12) -0.0034(12) C31 0.0239(13) 0.0189(13) 0.0374(15) -0.0046(11) 0.0026(11) 0.0006(10) C32 0.0293(14) 0.0232(15) 0.0370(16) -0.0024(12) 0.0032(12) -0.0039(11) C33 0.0315(16) 0.0237(15) 0.0447(17) 0.0003(12) -0.0044(13) -0.0015(12) C34 0.0241(14) 0.0265(15) 0.0539(19) -0.0029(14) -0.0048(13) 0.0019(11) C35 0.0256(15) 0.0293(16) 0.0545(19) -0.0036(14) 0.0093(13) 0.0009(12) C36 0.0270(14) 0.0293(16) 0.0390(16) -0.0001(12) 0.0056(12) 0.0023(12) Cl1 0.0368(5) 0.0645(6) 0.0549(5) 0.0063(4) 0.0072(4) -0.0039(4) Cl2 0.0406(5) 0.0793(7) 0.0551(6) 0.0061(5) 0.0082(4) -0.0112(4) Cl3 0.0746(7) 0.0612(7) 0.0807(8) -0.0166(5) -0.0039(6) 0.0209(5) C6 0.0326(16) 0.056(2) 0.0400(18) -0.0057(15) -0.0028(13) -0.0006(15) Cl4 0.0782(14) 0.0819(15) 0.0452(10) 0.0073(10) 0.0217(10) -0.0083(12) Cl5 0.0846(17) 0.0846(18) 0.119(2) 0.0501(16) 0.0053(15) -0.0018(13) Cl6 0.0614(14) 0.0803(18) 0.189(3) -0.064(2) -0.0316(18) 0.0051(13) C7 0.055(5) 0.054(5) 0.058(5) 0.005(4) 0.016(4) 0.007(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 O C5 1.371(3) . ? O C4 1.372(3) . ? N2 C4 1.284(4) . ? N2 N3 1.401(3) . ? N3 C5 1.296(4) . ? N4 C14 1.409(3) . ? N4 C31 1.421(3) . ? N4 C21 1.438(3) . ? C1 C3 1.349(4) 5_656 ? C1 C2 1.383(4) . ? C1 H1 0.9634 . ? C2 C3 1.383(4) . ? C2 C4 1.454(4) . ? C3 N1 1.349(4) 5_656 ? C3 C1 1.349(4) 5_656 ? C3 H3 0.89(3) . ? C5 C11 1.445(4) . ? C11 C16 1.401(4) . ? C11 C12 1.404(4) . ? C12 C13 1.381(4) . ? C12 H12 0.9483 . ? C13 C14 1.403(4) . ? C13 H13 0.9485 . ? C14 C15 1.398(4) . ? C15 C16 1.373(4) . ? C15 H15 0.9481 . ? C16 H16 0.9485 . ? C21 C26 1.382(4) . ? C21 C22 1.386(4) . ? C22 C23 1.382(4) . ? C22 H22 0.9483 . ? C23 C24 1.393(5) . ? C23 H23 0.9483 . ? C24 C25 1.379(5) . ? C24 H24 0.9482 . ? C25 C26 1.380(4) . ? C25 H25 0.9484 . ? C26 H26 0.9481 . ? C31 C32 1.388(4) . ? C31 C36 1.402(4) . ? C32 C33 1.390(4) . ? C32 H32 0.9482 . ? C33 C34 1.389(4) . ? C33 H33 0.9490 . ? C34 C35 1.376(4) . ? C34 H34 0.9484 . ? C35 C36 1.386(4) . ? C35 H35 0.9483 . ? C36 H36 0.9484 . ? Cl1 C6 1.756(4) . ? Cl2 C6 1.748(3) . ? Cl3 C6 1.762(4) . ? C6 D6 0.9984 . ? Cl4 C7 1.744(8) . ? Cl5 C7 1.734(9) . ? Cl6 C7 1.714(8) . ? C7 D7 0.9981 . ? 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 C5 O C4 102.4(2) . . ? C4 N2 N3 106.3(2) . . ? C5 N3 N2 106.9(2) . . ? C14 N4 C31 123.4(2) . . ? C14 N4 C21 117.7(2) . . ? C31 N4 C21 118.5(2) . . ? C3 C1 C2 118.4(3) 5_656 . ? C3 C1 H1 119.8 5_656 . ? C2 C1 H1 121.8 . . ? C3 C2 C1 120.6(3) . . ? C3 C2 C4 122.2(2) . . ? C1 C2 C4 117.2(3) . . ? N1 C3 C2 120.9(3) 5_656 . ? C1 C3 C2 120.9(3) 5_656 . ? N1 C3 H3 115(2) 5_656 . ? C1 C3 H3 115(2) 5_656 . ? C2 C3 H3 124(2) . . ? N2 C4 O 112.6(3) . . ? N2 C4 C2 127.8(3) . . ? O C4 C2 119.6(2) . . ? N3 C5 O 111.7(2) . . ? N3 C5 C11 127.9(3) . . ? O C5 C11 120.4(2) . . ? C16 C11 C12 118.7(2) . . ? C16 C11 C5 118.7(2) . . ? C12 C11 C5 122.6(2) . . ? C13 C12 C11 120.3(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.7(2) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 118.6(2) . . ? C15 C14 N4 120.2(2) . . ? C13 C14 N4 121.2(2) . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 120.8(2) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.5 . . ? C26 C21 C22 120.0(3) . . ? C26 C21 N4 120.4(2) . . ? C22 C21 N4 119.6(2) . . ? C23 C22 C21 119.3(3) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.6 . . ? C25 C24 C23 119.4(3) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 120.1(3) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.4(3) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C32 C31 C36 119.0(2) . . ? C32 C31 N4 120.0(2) . . ? C36 C31 N4 121.0(3) . . ? C31 C32 C33 120.6(3) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 120.0(3) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 120.1 . . ? C35 C34 C33 119.6(3) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.3 . . ? C34 C35 C36 120.9(3) . . ? C34 C35 H35 119.5 . . ? C36 C35 H35 119.5 . . ? C35 C36 C31 119.8(3) . . ? C35 C36 H36 120.0 . . ? C31 C36 H36 120.2 . . ? Cl2 C6 Cl1 110.13(18) . . ? Cl2 C6 Cl3 111.91(19) . . ? Cl1 C6 Cl3 109.60(19) . . ? Cl2 C6 D6 108.4 . . ? Cl1 C6 D6 108.4 . . ? Cl3 C6 D6 108.3 . . ? Cl6 C7 Cl5 111.8(4) . . ? Cl6 C7 Cl4 109.0(5) . . ? Cl5 C7 Cl4 110.7(5) . . ? Cl6 C7 D7 108.5 . . ? Cl5 C7 D7 108.4 . . ? Cl4 C7 D7 108.4 . . ? 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 N1 C2 C4 N2 -6.6(4) . . . . ? N3 C5 C11 C16 -2.5(4) . . . . ? C13 C14 N4 C31 32.1(4) . . . . ? C14 N4 C31 C36 28.9(4) . . . . ? C15 C14 N4 C21 23.9(4) . . . . ? C14 N4 C21 C22 56.6(3) . . . . ? 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 C6 D6 N3 1.00 2.26 3.247(4) 171.0 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.693 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.062 #=====================================END #====================================================================== data_(11) _database_code_depnum_ccdc_archive 'CCDC 602979' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(4-tert-butylphenyl)-5-(4-bromophenyl)-1,3,4-oxadiazole ; _chemical_name_common 2-(4-tert-butylphenyl)-5-(4-bromophenyl)-1,3,4-oxadiazole _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Br N2 O' _chemical_formula_sum 'C18 H17 Br N2 O' _chemical_formula_weight 357.25 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3569(11) _cell_length_b 6.1392(10) _cell_length_c 34.909(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.43(2) _cell_angle_gamma 90.00 _cell_volume 1576.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5629 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 27.28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 2.611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7375 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS 2.03 (Bruker, 2001)' _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 10s exposure), every run at a different \f angle. Crystal to detector distance 5.93 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '60W microfocus Bede Microsource with glass polycapillary optics' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ProteumM APEX CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 14799 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3504 _reflns_number_gt 3114 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 6.28A (Bruker, 2002)' _computing_data_reduction 'SAINT version 6.28A (Bruker, 2002)' _computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)' _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. Max/min \D\r features occur near the Br atom. ; _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^)+(0.0002P)^2^+20.0841P] 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 3504 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0760 _refine_ls_wR_factor_ref 0.1710 _refine_ls_wR_factor_gt 0.1678 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.158 _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 Br Br 0.79228(9) 0.82499(12) 0.08781(2) 0.0270(2) Uani 1 1 d . . . O O 0.4732(6) 0.6075(7) 0.26789(12) 0.0168(9) Uani 1 1 d . . . N1 N 0.3575(7) 0.2819(9) 0.28070(15) 0.0210(11) Uani 1 1 d . . . N2 N 0.4234(7) 0.2794(9) 0.24311(15) 0.0207(11) Uani 1 1 d . . . C1 C 0.3885(8) 0.4803(10) 0.29376(17) 0.0163(12) Uani 1 1 d . . . C2 C 0.4895(8) 0.4730(10) 0.23723(17) 0.0169(12) Uani 1 1 d . . . C11 C 0.3460(7) 0.5671(10) 0.33152(16) 0.0145(11) Uani 1 1 d . . . C12 C 0.4079(8) 0.7736(10) 0.34268(17) 0.0169(12) Uani 1 1 d . . . H12 H 0.4720 0.8630 0.3254 0.020 Uiso 1 1 d R . . C13 C 0.3763(9) 0.8473(10) 0.37941(18) 0.0207(13) Uani 1 1 d . . . H13 H 0.4213 0.9859 0.3872 0.025 Uiso 1 1 d R . . C14 C 0.2780(8) 0.7218(10) 0.40564(16) 0.0161(12) Uani 1 1 d . . . C15 C 0.2120(8) 0.5208(10) 0.39306(17) 0.0176(12) Uani 1 1 d . . . H15 H 0.1420 0.4350 0.4099 0.021 Uiso 1 1 d R . . C16 C 0.2477(8) 0.4424(10) 0.35651(17) 0.0159(12) Uani 1 1 d . . . H16 H 0.2024 0.3040 0.3487 0.019 Uiso 1 1 d R . . C17 C 0.2636(9) 0.7936(10) 0.44759(17) 0.0187(12) Uani 1 1 d . . . C18 C 0.4488(10) 0.7509(13) 0.46781(19) 0.0309(16) Uani 1 1 d . . . H18A H 0.4829 0.5979 0.4644 0.046 Uiso 1 1 d R . . H18B H 0.4392 0.7824 0.4952 0.046 Uiso 1 1 d R . . H18C H 0.5419 0.8448 0.4569 0.046 Uiso 1 1 d R . . C19 C 0.2207(9) 1.0378(10) 0.45056(18) 0.0211(13) Uani 1 1 d . . . H19A H 0.3187 1.1226 0.4393 0.032 Uiso 1 1 d R . . H19B H 0.2100 1.0775 0.4776 0.032 Uiso 1 1 d R . . H19C H 0.1058 1.0690 0.4368 0.032 Uiso 1 1 d R . . C20 C 0.1163(12) 0.6688(13) 0.4687(2) 0.0360(18) Uani 1 1 d . . . H20A H -0.0026 0.6967 0.4564 0.054 Uiso 1 1 d R . . H20B H 0.1145 0.7174 0.4955 0.054 Uiso 1 1 d R . . H20C H 0.1424 0.5122 0.4679 0.054 Uiso 1 1 d R . . C21 C 0.5685(7) 0.5559(10) 0.20227(17) 0.0153(12) Uani 1 1 d . . . C22 C 0.6392(8) 0.7688(10) 0.20072(18) 0.0185(12) Uani 1 1 d . . . H22 H 0.6415 0.8585 0.2229 0.022 Uiso 1 1 d R . . C23 C 0.7063(8) 0.8470(11) 0.16649(18) 0.0204(13) Uani 1 1 d . . . H23 H 0.7512 0.9918 0.1649 0.024 Uiso 1 1 d R . . C24 C 0.7063(8) 0.7142(10) 0.13499(17) 0.0190(13) Uani 1 1 d . . . C25 C 0.6388(9) 0.5011(11) 0.13603(19) 0.0213(13) Uani 1 1 d . . . H25 H 0.6413 0.4101 0.1140 0.026 Uiso 1 1 d R . . C26 C 0.5687(8) 0.4254(11) 0.16975(18) 0.0188(12) Uani 1 1 d . . . H26 H 0.5211 0.2817 0.1707 0.023 Uiso 1 1 d 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 Br 0.0225(3) 0.0334(4) 0.0253(3) 0.0115(3) 0.0065(2) 0.0033(3) O 0.018(2) 0.015(2) 0.018(2) -0.0008(17) 0.0034(16) 0.0012(17) N1 0.026(3) 0.018(3) 0.019(2) -0.001(2) 0.002(2) -0.009(2) N2 0.025(3) 0.017(3) 0.020(2) -0.001(2) 0.002(2) -0.003(2) C1 0.014(3) 0.013(3) 0.022(3) -0.002(2) 0.000(2) 0.003(2) C2 0.017(3) 0.016(3) 0.018(3) -0.001(2) -0.003(2) 0.000(2) C11 0.011(3) 0.016(3) 0.016(3) 0.001(2) -0.007(2) -0.001(2) C12 0.015(3) 0.013(3) 0.022(3) 0.003(2) -0.002(2) -0.004(2) C13 0.026(3) 0.013(3) 0.023(3) 0.000(3) 0.001(2) -0.004(3) C14 0.018(3) 0.013(3) 0.018(3) 0.003(2) 0.001(2) 0.001(2) C15 0.019(3) 0.014(3) 0.019(3) 0.003(2) -0.001(2) 0.000(2) C16 0.016(3) 0.010(3) 0.022(3) 0.000(2) -0.004(2) -0.001(2) C17 0.028(3) 0.011(3) 0.017(3) 0.000(2) 0.002(2) -0.001(3) C18 0.040(4) 0.030(4) 0.023(3) -0.001(3) -0.004(3) 0.014(3) C19 0.028(3) 0.015(3) 0.021(3) -0.003(2) -0.002(3) 0.003(3) C20 0.059(5) 0.028(4) 0.022(3) -0.005(3) 0.018(3) -0.013(4) C21 0.009(2) 0.018(3) 0.019(3) 0.000(2) -0.004(2) -0.002(2) C22 0.018(3) 0.015(3) 0.022(3) 0.000(2) 0.000(2) -0.004(2) C23 0.020(3) 0.014(3) 0.027(3) 0.005(3) -0.002(2) 0.004(3) C24 0.019(3) 0.019(3) 0.019(3) 0.007(2) 0.004(2) 0.001(2) C25 0.021(3) 0.020(3) 0.023(3) -0.003(3) 0.001(2) 0.000(3) C26 0.016(3) 0.018(3) 0.022(3) -0.001(2) 0.000(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br C24 1.905(6) . ? O C1 1.357(7) . ? O C2 1.359(7) . ? N1 C1 1.318(8) . ? N1 N2 1.410(7) . ? N2 C2 1.302(8) . ? C1 C11 1.463(8) . ? C2 C21 1.457(8) . ? C11 C16 1.379(8) . ? C11 C12 1.399(8) . ? C12 C13 1.385(9) . ? C13 C14 1.410(8) . ? C14 C15 1.393(8) . ? C14 C17 1.536(8) . ? C15 C16 1.395(8) . ? C17 C20 1.532(9) . ? C17 C19 1.536(8) . ? C17 C18 1.542(9) . ? C21 C26 1.390(8) . ? C21 C22 1.408(9) . ? C22 C23 1.390(9) . ? C23 C24 1.369(9) . ? C24 C25 1.400(9) . ? C25 C26 1.378(9) . ? 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 O C2 103.0(5) . . ? C1 N1 N2 105.7(5) . . ? C2 N2 N1 106.0(5) . . ? N1 C1 O 112.3(5) . . ? N1 C1 C11 127.5(6) . . ? O C1 C11 120.1(5) . . ? N2 C2 O 112.9(5) . . ? N2 C2 C21 127.5(6) . . ? O C2 C21 119.5(5) . . ? C16 C11 C12 119.9(6) . . ? C16 C11 C1 119.7(5) . . ? C12 C11 C1 120.4(6) . . ? C13 C12 C11 119.5(6) . . ? C12 C13 C14 121.5(6) . . ? C15 C14 C13 117.4(5) . . ? C15 C14 C17 121.5(5) . . ? C13 C14 C17 120.7(5) . . ? C14 C15 C16 121.5(6) . . ? C11 C16 C15 120.0(6) . . ? C20 C17 C14 112.5(5) . . ? C20 C17 C19 107.9(6) . . ? C14 C17 C19 111.3(5) . . ? C20 C17 C18 108.8(6) . . ? C14 C17 C18 107.8(5) . . ? C19 C17 C18 108.4(5) . . ? C26 C21 C22 119.7(6) . . ? C26 C21 C2 119.5(6) . . ? C22 C21 C2 120.8(6) . . ? C23 C22 C21 119.6(6) . . ? C24 C23 C22 119.5(6) . . ? C23 C24 C25 121.9(6) . . ? C23 C24 Br 119.2(5) . . ? C25 C24 Br 118.8(5) . . ? C26 C25 C24 118.6(6) . . ? C25 C26 C21 120.8(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 C21 C2 O 4.3(9) . . . . ? C21 C2 O C1 177.3(5) . . . . ? C2 O C1 C11 179.8(5) . . . . ? O C1 C11 C12 -6.4(8) . . . . ? C13 C14 C17 C19 45.0(8) . . . . ? C15 C14 C17 C20 -20.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 2.007 _refine_diff_density_min -2.067 _refine_diff_density_rms 0.141