Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Tahsin Chow' _publ_contact_author_email TJCHOW@CHEM.SINICA.EDU.TW _publ_section_title ; White Light-Emitting Devices with Single Emitting Layer Based on Bisindolylmaleimide Fluorophores ; loop_ _publ_author_name 'Tahsin Chow.' 'Zhenghuan Lin.' 'Yuh-Sheng Wen.' # Attachment 'i9915_revised.cif' data_i9915 _database_code_depnum_ccdc_archive 'CCDC 715885' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H31 N3 O2,CH2Cl2' _chemical_formula_sum 'C42 H33 Cl2 N3 O2' _chemical_formula_weight 682.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 20.9958(9) _cell_length_b 7.6820(3) _cell_length_c 22.6056(10) _cell_angle_alpha 90.00 _cell_angle_beta 113.5850(10) _cell_angle_gamma 90.00 _cell_volume 3341.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 3995 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 24.69 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.125 _exptl_absorpt_correction_T_max 0.205 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21248 _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5886 _reflns_number_gt 3336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+0.6506P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5886 _refine_ls_number_parameters 443 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1066 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Cl1 Cl 0.18696(5) 0.45978(11) 0.29435(4) 0.0522(3) Uani 1 1 d . . . Cl2 Cl 0.20864(5) 0.46609(11) 0.43015(4) 0.0551(3) Uani 1 1 d . . . O1 O 0.32987(10) 0.7266(2) 0.11689(9) 0.0326(5) Uani 1 1 d . . . O2 O 0.11843(11) 0.7805(2) 0.12662(9) 0.0337(5) Uani 1 1 d . . . N1 N 0.21624(12) 0.7305(3) 0.10677(11) 0.0256(6) Uani 1 1 d . . . N15 N 0.48040(12) 0.9528(3) 0.29824(11) 0.0264(6) Uani 1 1 d . . . N31 N 0.14786(13) 1.0233(3) 0.30433(11) 0.0282(6) Uani 1 1 d . . . C2 C 0.28722(15) 0.7625(3) 0.13874(14) 0.0262(7) Uani 1 1 d . . . C3 C 0.29796(15) 0.8484(3) 0.20105(13) 0.0237(7) Uani 1 1 d . . . C4 C 0.23558(15) 0.8583(3) 0.20573(13) 0.0240(7) Uani 1 1 d . . . C5 C 0.18121(16) 0.7870(3) 0.14373(14) 0.0260(7) Uani 1 1 d . . . C6 C 0.18155(16) 0.6668(4) 0.04052(13) 0.0314(8) Uani 1 1 d . . . H6A H 0.2133 0.6768 0.0192 0.038 Uiso 1 1 calc R . . H6B H 0.1418 0.7406 0.0175 0.038 Uiso 1 1 calc R . . C7 C 0.15730(16) 0.4811(4) 0.03601(13) 0.0268(7) Uani 1 1 d . . . C8 C 0.20183(17) 0.3490(4) 0.07005(15) 0.0392(9) Uani 1 1 d . . . H8 H 0.2473 0.3751 0.0976 0.047 Uiso 1 1 calc R . . C9 C 0.17896(19) 0.1792(4) 0.06328(17) 0.0478(10) Uani 1 1 d . . . H9 H 0.2089 0.0915 0.0868 0.057 Uiso 1 1 calc R . . C10 C 0.11186(19) 0.1383(4) 0.02185(16) 0.0446(9) Uani 1 1 d . . . H10 H 0.0969 0.0232 0.0170 0.053 Uiso 1 1 calc R . . C11 C 0.06725(17) 0.2679(4) -0.01214(15) 0.0393(9) Uani 1 1 d . . . H11 H 0.0220 0.2410 -0.0401 0.047 Uiso 1 1 calc R . . C12 C 0.08995(16) 0.4385(4) -0.00466(14) 0.0338(8) Uani 1 1 d . . . H12 H 0.0594 0.5262 -0.0274 0.041 Uiso 1 1 calc R . . C13 C 0.36502(15) 0.9223(3) 0.24165(13) 0.0242(7) Uani 1 1 d . . . C14 C 0.42850(15) 0.8433(4) 0.26054(13) 0.0272(7) Uani 1 1 d . . . H14 H 0.4355 0.7306 0.2493 0.033 Uiso 1 1 calc R . . C16 C 0.45020(15) 1.1087(3) 0.30453(13) 0.0245(7) Uani 1 1 d . . . C17 C 0.48132(16) 1.2597(4) 0.33779(14) 0.0327(8) Uani 1 1 d . . . H17 H 0.5290 1.2664 0.3618 0.039 Uiso 1 1 calc R . . C18 C 0.43792(16) 1.3994(4) 0.33344(14) 0.0328(8) Uani 1 1 d . . . H18 H 0.4569 1.5018 0.3554 0.039 Uiso 1 1 calc R . . C19 C 0.36623(16) 1.3902(4) 0.29687(15) 0.0349(8) Uani 1 1 d . . . H19 H 0.3388 1.4874 0.2940 0.042 Uiso 1 1 calc R . . C20 C 0.33556(15) 1.2397(4) 0.26495(14) 0.0304(8) Uani 1 1 d . . . H20 H 0.2878 1.2339 0.2414 0.036 Uiso 1 1 calc R . . C21 C 0.37787(15) 1.0959(3) 0.26880(13) 0.0255(7) Uani 1 1 d . . . C22 C 0.55279(15) 0.9010(4) 0.33335(14) 0.0307(8) Uani 1 1 d . . . H22A H 0.5813 1.0046 0.3475 0.037 Uiso 1 1 calc R . . H22B H 0.5682 0.8376 0.3044 0.037 Uiso 1 1 calc R . . C23 C 0.56330(15) 0.7882(4) 0.39147(14) 0.0271(7) Uani 1 1 d . . . C24 C 0.53241(15) 0.8316(4) 0.43377(14) 0.0318(8) Uani 1 1 d . . . H24 H 0.5047 0.9304 0.4262 0.038 Uiso 1 1 calc R . . C25 C 0.54279(16) 0.7283(4) 0.48692(15) 0.0372(8) Uani 1 1 d . . . H25 H 0.5222 0.7581 0.5151 0.045 Uiso 1 1 calc R . . C26 C 0.58370(16) 0.5806(4) 0.49834(15) 0.0379(8) Uani 1 1 d . . . H26 H 0.5909 0.5117 0.5343 0.046 Uiso 1 1 calc R . . C27 C 0.61375(17) 0.5359(4) 0.45636(15) 0.0391(9) Uani 1 1 d . . . H27 H 0.6410 0.4362 0.4638 0.047 Uiso 1 1 calc R . . C28 C 0.60350(15) 0.6395(4) 0.40295(15) 0.0346(8) Uani 1 1 d . . . H28 H 0.6239 0.6086 0.3747 0.042 Uiso 1 1 calc R . . C29 C 0.21602(15) 0.9181(3) 0.25642(14) 0.0239(7) Uani 1 1 d . . . C30 C 0.15048(16) 0.9744(3) 0.24749(14) 0.0289(7) Uani 1 1 d . . . H30 H 0.1129 0.9784 0.2077 0.035 Uiso 1 1 calc R . . C32 C 0.21269(16) 0.9947(3) 0.35349(14) 0.0269(7) Uani 1 1 d . . . C33 C 0.23395(17) 1.0187(4) 0.41960(14) 0.0324(8) Uani 1 1 d . . . H33 H 0.2038 1.0627 0.4369 0.039 Uiso 1 1 calc R . . C34 C 0.30140(17) 0.9747(4) 0.45855(15) 0.0365(8) Uani 1 1 d . . . H34 H 0.3174 0.9904 0.5029 0.044 Uiso 1 1 calc R . . C35 C 0.34610(16) 0.9069(4) 0.43251(15) 0.0332(8) Uani 1 1 d . . . H35 H 0.3913 0.8777 0.4600 0.040 Uiso 1 1 calc R . . C36 C 0.32492(16) 0.8821(4) 0.36694(14) 0.0290(7) Uani 1 1 d . . . H36 H 0.3552 0.8351 0.3504 0.035 Uiso 1 1 calc R . . C37 C 0.25690(15) 0.9287(3) 0.32544(14) 0.0238(7) Uani 1 1 d . . . C38 C 0.08646(15) 1.0880(4) 0.31187(15) 0.0339(8) Uani 1 1 d . . . H38A H 0.0557 1.1405 0.2715 0.041 Uiso 1 1 calc R . . H38B H 0.1005 1.1784 0.3445 0.041 Uiso 1 1 calc R . . C39 C 0.04647(16) 0.9496(4) 0.33082(13) 0.0295(8) Uani 1 1 d . . . C40 C 0.07164(16) 0.7815(4) 0.34708(14) 0.0368(8) Uani 1 1 d . . . H40 H 0.1126 0.7484 0.3437 0.044 Uiso 1 1 calc R . . C41 C 0.03566(17) 0.6624(4) 0.36847(15) 0.0428(9) Uani 1 1 d . . . H41 H 0.0527 0.5499 0.3793 0.051 Uiso 1 1 calc R . . C42 C -0.02494(18) 0.7101(5) 0.37365(15) 0.0450(9) Uani 1 1 d . . . H42 H -0.0481 0.6309 0.3892 0.054 Uiso 1 1 calc R . . C43 C -0.05153(17) 0.8749(5) 0.35590(15) 0.0432(9) Uani 1 1 d . . . H43 H -0.0933 0.9061 0.3581 0.052 Uiso 1 1 calc R . . C44 C -0.01576(16) 0.9939(4) 0.33471(14) 0.0370(8) Uani 1 1 d . . . H44 H -0.0337 1.1053 0.3229 0.044 Uiso 1 1 calc R . . C50 C 0.24864(17) 0.4608(4) 0.37480(16) 0.0491(10) Uani 1 1 d . . . H50A H 0.2785 0.5617 0.3816 0.059 Uiso 1 1 calc R . . H50B H 0.2774 0.3575 0.3825 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0474(6) 0.0492(6) 0.0539(6) 0.0020(4) 0.0139(5) -0.0012(4) Cl2 0.0514(6) 0.0546(6) 0.0566(6) -0.0032(5) 0.0188(5) 0.0070(5) O1 0.0307(13) 0.0367(13) 0.0344(13) -0.0044(10) 0.0175(11) -0.0005(10) O2 0.0243(13) 0.0420(13) 0.0318(13) -0.0034(10) 0.0079(11) -0.0038(10) N1 0.0220(15) 0.0303(14) 0.0243(14) -0.0031(11) 0.0090(12) -0.0008(11) N15 0.0206(15) 0.0305(14) 0.0268(14) -0.0019(11) 0.0082(12) -0.0004(12) N31 0.0284(16) 0.0311(14) 0.0280(15) -0.0001(12) 0.0142(13) 0.0042(12) C2 0.025(2) 0.0244(17) 0.0297(18) 0.0039(14) 0.0107(16) 0.0004(14) C3 0.0250(18) 0.0213(15) 0.0241(17) 0.0017(13) 0.0093(15) 0.0017(13) C4 0.0258(18) 0.0211(16) 0.0233(17) -0.0020(13) 0.0079(15) -0.0031(13) C5 0.027(2) 0.0240(16) 0.0279(18) 0.0007(14) 0.0114(16) -0.0044(14) C6 0.036(2) 0.0301(18) 0.0249(18) -0.0026(14) 0.0088(16) 0.0000(15) C7 0.034(2) 0.0272(17) 0.0195(17) 0.0009(13) 0.0106(16) 0.0025(14) C8 0.036(2) 0.040(2) 0.037(2) 0.0033(16) 0.0091(17) 0.0024(17) C9 0.058(3) 0.032(2) 0.052(2) 0.0147(17) 0.021(2) 0.0108(18) C10 0.061(3) 0.0304(19) 0.049(2) -0.0068(17) 0.029(2) -0.0072(19) C11 0.040(2) 0.044(2) 0.032(2) -0.0047(16) 0.0122(17) -0.0091(17) C12 0.034(2) 0.0357(19) 0.0267(18) -0.0033(15) 0.0068(16) -0.0023(16) C13 0.0232(18) 0.0266(16) 0.0242(17) 0.0008(13) 0.0110(15) -0.0010(14) C14 0.0268(19) 0.0277(16) 0.0293(18) -0.0030(14) 0.0136(15) -0.0038(14) C16 0.0270(19) 0.0244(16) 0.0244(17) -0.0001(13) 0.0125(15) -0.0002(14) C17 0.0281(19) 0.0364(19) 0.0322(19) -0.0030(15) 0.0106(16) -0.0037(15) C18 0.039(2) 0.0269(18) 0.036(2) -0.0041(14) 0.0177(17) -0.0059(15) C19 0.035(2) 0.0281(18) 0.043(2) -0.0003(15) 0.0172(18) 0.0009(15) C20 0.0255(19) 0.0303(18) 0.0341(19) 0.0030(15) 0.0106(16) 0.0023(14) C21 0.0308(19) 0.0250(16) 0.0240(17) 0.0004(13) 0.0144(15) -0.0029(14) C22 0.0244(19) 0.0337(18) 0.0329(19) -0.0037(15) 0.0103(16) -0.0020(14) C23 0.0224(18) 0.0269(17) 0.0295(18) -0.0029(14) 0.0078(15) -0.0039(14) C24 0.0291(19) 0.0304(17) 0.034(2) -0.0015(15) 0.0107(16) 0.0025(14) C25 0.038(2) 0.044(2) 0.032(2) -0.0039(16) 0.0158(17) -0.0049(17) C26 0.036(2) 0.039(2) 0.033(2) 0.0018(16) 0.0076(17) -0.0020(16) C27 0.034(2) 0.0344(19) 0.041(2) -0.0039(17) 0.0059(18) 0.0017(15) C28 0.029(2) 0.0377(19) 0.034(2) -0.0023(16) 0.0094(16) 0.0012(16) C29 0.0219(18) 0.0248(16) 0.0262(17) 0.0014(13) 0.0108(15) -0.0026(13) C30 0.030(2) 0.0308(17) 0.0260(18) 0.0017(14) 0.0118(16) -0.0020(15) C32 0.0287(19) 0.0250(17) 0.0276(18) 0.0021(14) 0.0119(16) -0.0009(14) C33 0.036(2) 0.0357(18) 0.0299(19) -0.0015(15) 0.0175(17) -0.0045(15) C34 0.040(2) 0.045(2) 0.0274(19) -0.0034(16) 0.0160(18) -0.0070(17) C35 0.0252(19) 0.0386(19) 0.032(2) 0.0020(15) 0.0079(16) -0.0041(15) C36 0.031(2) 0.0256(17) 0.0338(19) -0.0018(14) 0.0165(16) -0.0046(14) C37 0.0220(18) 0.0249(16) 0.0274(18) 0.0004(13) 0.0130(15) -0.0018(13) C38 0.033(2) 0.0392(19) 0.0318(19) 0.0024(15) 0.0149(16) 0.0088(15) C39 0.0288(19) 0.0387(19) 0.0219(17) -0.0036(14) 0.0109(15) -0.0009(15) C40 0.031(2) 0.041(2) 0.038(2) 0.0013(16) 0.0140(17) -0.0011(16) C41 0.041(2) 0.044(2) 0.041(2) -0.0024(17) 0.0147(19) -0.0094(18) C42 0.042(2) 0.063(3) 0.035(2) -0.0088(18) 0.0213(19) -0.023(2) C43 0.025(2) 0.068(3) 0.041(2) -0.0123(19) 0.0181(18) -0.0112(19) C44 0.029(2) 0.052(2) 0.0294(19) -0.0063(16) 0.0106(17) 0.0025(17) C50 0.038(2) 0.043(2) 0.060(2) 0.0076(18) 0.013(2) -0.0058(17) _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 Cl1 C50 1.761(3) . ? Cl2 C50 1.764(4) . ? O1 C2 1.215(3) . ? O2 C5 1.217(3) . ? N1 C5 1.386(4) . ? N1 C2 1.394(3) . ? N1 C6 1.463(3) . ? N15 C14 1.371(3) . ? N15 C16 1.389(3) . ? N15 C22 1.460(3) . ? N31 C30 1.361(3) . ? N31 C32 1.388(3) . ? N31 C38 1.454(4) . ? C2 C3 1.488(4) . ? C3 C4 1.358(4) . ? C3 C13 1.454(4) . ? C4 C29 1.438(4) . ? C4 C5 1.512(4) . ? C6 C7 1.505(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.383(4) . ? C7 C8 1.386(4) . ? C8 C9 1.377(4) . ? C8 H8 0.9300 . ? C9 C10 1.380(4) . ? C9 H9 0.9300 . ? C10 C11 1.372(4) . ? C10 H10 0.9300 . ? C11 C12 1.382(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.368(4) . ? C13 C21 1.448(4) . ? C14 H14 0.9300 . ? C16 C17 1.395(4) . ? C16 C21 1.409(4) . ? C17 C18 1.385(4) . ? C17 H17 0.9300 . ? C18 C19 1.399(4) . ? C18 H18 0.9300 . ? C19 C20 1.378(4) . ? C19 H19 0.9300 . ? C20 C21 1.398(4) . ? C20 H20 0.9300 . ? C22 C23 1.515(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C28 1.382(4) . ? C23 C24 1.393(4) . ? C24 C25 1.382(4) . ? C24 H24 0.9300 . ? C25 C26 1.383(4) . ? C25 H25 0.9300 . ? C26 C27 1.377(4) . ? C26 H26 0.9300 . ? C27 C28 1.389(4) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.378(4) . ? C29 C37 1.451(4) . ? C30 H30 0.9300 . ? C32 C33 1.390(4) . ? C32 C37 1.411(4) . ? C33 C34 1.377(4) . ? C33 H33 0.9300 . ? C34 C35 1.393(4) . ? C34 H34 0.9300 . ? C35 C36 1.380(4) . ? C35 H35 0.9300 . ? C36 C37 1.406(4) . ? C36 H36 0.9300 . ? C38 C39 1.519(4) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.388(4) . ? C39 C44 1.386(4) . ? C40 C41 1.391(4) . ? C40 H40 0.9300 . ? C41 C42 1.373(4) . ? C41 H41 0.9300 . ? C42 C43 1.377(5) . ? C42 H42 0.9300 . ? C43 C44 1.385(4) . ? C43 H43 0.9300 . ? C44 H44 0.9300 . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? 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 N1 C2 110.3(2) . . ? C5 N1 C6 123.7(2) . . ? C2 N1 C6 125.5(2) . . ? C14 N15 C16 108.1(2) . . ? C14 N15 C22 124.5(2) . . ? C16 N15 C22 126.7(2) . . ? C30 N31 C32 108.4(2) . . ? C30 N31 C38 125.3(3) . . ? C32 N31 C38 126.3(2) . . ? O1 C2 N1 123.9(3) . . ? O1 C2 C3 128.9(3) . . ? N1 C2 C3 107.2(3) . . ? C4 C3 C13 130.5(3) . . ? C4 C3 C2 108.2(2) . . ? C13 C3 C2 120.8(3) . . ? C3 C4 C29 132.2(3) . . ? C3 C4 C5 107.5(3) . . ? C29 C4 C5 120.2(3) . . ? O2 C5 N1 124.3(3) . . ? O2 C5 C4 129.0(3) . . ? N1 C5 C4 106.6(2) . . ? N1 C6 C7 113.7(2) . . ? N1 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? N1 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C12 C7 C8 118.7(3) . . ? C12 C7 C6 119.8(3) . . ? C8 C7 C6 121.5(3) . . ? C9 C8 C7 120.3(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.7(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 121.1(3) . . ? C7 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C21 106.5(2) . . ? C14 C13 C3 126.9(3) . . ? C21 C13 C3 126.7(3) . . ? C13 C14 N15 110.8(3) . . ? C13 C14 H14 124.6 . . ? N15 C14 H14 124.6 . . ? N15 C16 C17 129.6(3) . . ? N15 C16 C21 108.2(2) . . ? C17 C16 C21 122.1(3) . . ? C18 C17 C16 116.9(3) . . ? C18 C17 H17 121.5 . . ? C16 C17 H17 121.5 . . ? C17 C18 C19 121.6(3) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? C20 C19 C18 121.2(3) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 118.5(3) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C16 119.5(3) . . ? C20 C21 C13 134.1(3) . . ? C16 C21 C13 106.4(2) . . ? N15 C22 C23 112.7(2) . . ? N15 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? N15 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? C28 C23 C24 119.1(3) . . ? C28 C23 C22 120.1(3) . . ? C24 C23 C22 120.8(3) . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 120.2(3) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C27 C26 C25 119.8(3) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C28 120.1(3) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C23 C28 C27 120.5(3) . . ? C23 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C30 C29 C4 124.8(3) . . ? C30 C29 C37 105.4(3) . . ? C4 C29 C37 129.8(3) . . ? N31 C30 C29 111.3(3) . . ? N31 C30 H30 124.3 . . ? C29 C30 H30 124.3 . . ? N31 C32 C33 129.1(3) . . ? N31 C32 C37 107.9(2) . . ? C33 C32 C37 123.0(3) . . ? C34 C33 C32 117.4(3) . . ? C34 C33 H33 121.3 . . ? C32 C33 H33 121.3 . . ? C33 C34 C35 121.0(3) . . ? C33 C34 H34 119.5 . . ? C35 C34 H34 119.5 . . ? C36 C35 C34 121.6(3) . . ? C36 C35 H35 119.2 . . ? C34 C35 H35 119.2 . . ? C35 C36 C37 119.1(3) . . ? C35 C36 H36 120.4 . . ? C37 C36 H36 120.4 . . ? C36 C37 C32 117.8(3) . . ? C36 C37 C29 135.2(3) . . ? C32 C37 C29 106.9(2) . . ? N31 C38 C39 114.2(2) . . ? N31 C38 H38A 108.7 . . ? C39 C38 H38A 108.7 . . ? N31 C38 H38B 108.7 . . ? C39 C38 H38B 108.7 . . ? H38A C38 H38B 107.6 . . ? C40 C39 C44 118.7(3) . . ? C40 C39 C38 122.1(3) . . ? C44 C39 C38 119.2(3) . . ? C39 C40 C41 120.1(3) . . ? C39 C40 H40 119.9 . . ? C41 C40 H40 119.9 . . ? C42 C41 C40 120.3(3) . . ? C42 C41 H41 119.9 . . ? C40 C41 H41 119.9 . . ? C41 C42 C43 120.1(3) . . ? C41 C42 H42 119.9 . . ? C43 C42 H42 119.9 . . ? C42 C43 C44 119.7(3) . . ? C42 C43 H43 120.2 . . ? C44 C43 H43 120.2 . . ? C43 C44 C39 121.0(3) . . ? C43 C44 H44 119.5 . . ? C39 C44 H44 119.5 . . ? Cl1 C50 Cl2 111.74(19) . . ? Cl1 C50 H50A 109.3 . . ? Cl2 C50 H50A 109.3 . . ? Cl1 C50 H50B 109.3 . . ? Cl2 C50 H50B 109.3 . . ? H50A C50 H50B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.268 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.059 # Attachment 'i9989_revised.cif' data_i9989 _database_code_depnum_ccdc_archive 'CCDC 715886' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H26 F5 N3 O2,CH2Cl2 ' _chemical_formula_sum 'C42 H28 Cl2 F5 N3 O2' _chemical_formula_weight 772.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 20.2844(14) _cell_length_b 8.0018(6) _cell_length_c 22.3701(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.289(3) _cell_angle_gamma 90.00 _cell_volume 3572.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used 3149 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 20.97 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS, 1996' _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 0.745 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23167 _diffrn_reflns_av_R_equivalents 0.1055 _diffrn_reflns_av_sigmaI/netI 0.1447 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6105 _reflns_number_gt 2738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6105 _refine_ls_number_parameters 488 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1707 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1841 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 Cl1 Cl 0.67003(11) 0.5723(2) 0.28105(8) 0.1052(7) Uani 1 1 d . . . Cl2 Cl 0.52754(13) 0.6112(4) 0.27664(13) 0.1823(13) Uani 1 1 d . . . F8 F 0.76572(12) 0.5974(3) 0.14584(12) 0.0506(8) Uani 1 1 d . . . F9 F 0.70932(14) 0.9010(4) 0.14256(14) 0.0647(9) Uani 1 1 d . . . F10 F 0.57412(15) 0.9333(4) 0.11695(15) 0.0725(9) Uani 1 1 d . . . F11 F 0.49687(15) 0.6566(4) 0.09336(19) 0.0984(13) Uani 1 1 d . . . F12 F 0.55301(13) 0.3545(4) 0.09226(16) 0.0760(10) Uani 1 1 d . . . O1 O 0.83720(14) 0.2535(4) 0.16054(13) 0.0343(8) Uani 1 1 d . . . O2 O 0.63722(14) 0.1846(4) 0.22193(13) 0.0394(8) Uani 1 1 d . . . N1 N 0.72927(16) 0.2500(4) 0.17935(15) 0.0287(9) Uani 1 1 d . . . N15 N 0.98864(16) 0.0489(5) 0.30564(15) 0.0305(9) Uani 1 1 d . . . N31 N 0.68036(18) -0.0380(5) 0.40012(18) 0.0365(10) Uani 1 1 d . . . C2 C 0.7972(2) 0.2193(5) 0.1936(2) 0.0294(11) Uani 1 1 d . . . C3 C 0.8107(2) 0.1388(5) 0.25474(18) 0.0282(11) Uani 1 1 d . . . C4 C 0.7516(2) 0.1259(5) 0.27428(18) 0.0289(11) Uani 1 1 d . . . C5 C 0.6977(2) 0.1877(5) 0.2251(2) 0.0302(11) Uani 1 1 d . . . C6 C 0.6935(2) 0.2970(5) 0.11980(19) 0.0303(11) Uani 1 1 d . . . H6A H 0.6590 0.2144 0.1063 0.036 Uiso 1 1 calc R . . H6B H 0.7244 0.2960 0.0914 0.036 Uiso 1 1 calc R . . C7 C 0.6614(2) 0.4668(6) 0.11866(19) 0.0299(11) Uani 1 1 d . . . C8 C 0.6983(2) 0.6102(6) 0.13180(19) 0.0353(12) Uani 1 1 d . . . C9 C 0.6703(3) 0.7650(6) 0.1312(2) 0.0423(13) Uani 1 1 d . . . C10 C 0.6022(3) 0.7825(7) 0.1174(2) 0.0464(13) Uani 1 1 d . . . C11 C 0.5640(2) 0.6421(8) 0.1052(2) 0.0567(15) Uani 1 1 d . . . C12 C 0.5934(2) 0.4876(7) 0.1058(2) 0.0464(14) Uani 1 1 d . . . C13 C 0.8759(2) 0.0747(6) 0.27960(19) 0.0291(11) Uani 1 1 d . . . C14 C 0.9370(2) 0.1492(6) 0.28054(18) 0.0313(11) Uani 1 1 d . . . H14 H 0.9425 0.2560 0.2657 0.038 Uiso 1 1 calc R . . C16 C 0.9619(2) -0.1023(6) 0.32216(18) 0.0300(11) Uani 1 1 d . . . C17 C 0.9935(2) -0.2463(6) 0.34782(19) 0.0342(12) Uani 1 1 d . . . H17 H 1.0399 -0.2522 0.3585 0.041 Uiso 1 1 calc R . . C18 C 0.9537(2) -0.3793(6) 0.3568(2) 0.0434(13) Uani 1 1 d . . . H18 H 0.9735 -0.4768 0.3742 0.052 Uiso 1 1 calc R . . C19 C 0.8838(2) -0.3705(6) 0.3400(2) 0.0428(13) Uani 1 1 d . . . H19 H 0.8581 -0.4635 0.3458 0.051 Uiso 1 1 calc R . . C20 C 0.8522(2) -0.2281(6) 0.3153(2) 0.0363(12) Uani 1 1 d . . . H20 H 0.8057 -0.2238 0.3049 0.044 Uiso 1 1 calc R . . C21 C 0.8912(2) -0.0899(6) 0.30604(18) 0.0286(11) Uani 1 1 d . . . C22 C 1.0578(2) 0.1036(6) 0.3212(2) 0.0362(12) Uani 1 1 d . . . H22A H 1.0694 0.1653 0.2872 0.043 Uiso 1 1 calc R . . H22B H 1.0866 0.0063 0.3279 0.043 Uiso 1 1 calc R . . C23 C 1.0704(2) 0.2125(6) 0.3771(2) 0.0321(11) Uani 1 1 d . . . C24 C 1.1135(2) 0.3483(6) 0.3800(2) 0.0415(13) Uani 1 1 d . . . H24 H 1.1325 0.3758 0.3464 0.050 Uiso 1 1 calc R . . C25 C 1.1284(3) 0.4426(6) 0.4322(2) 0.0529(14) Uani 1 1 d . . . H25 H 1.1581 0.5318 0.4338 0.064 Uiso 1 1 calc R . . C26 C 1.0998(3) 0.4058(7) 0.4818(2) 0.0515(14) Uani 1 1 d . . . H26 H 1.1103 0.4693 0.5171 0.062 Uiso 1 1 calc R . . C27 C 1.0560(2) 0.2755(7) 0.4791(2) 0.0463(14) Uani 1 1 d . . . H27 H 1.0360 0.2515 0.5124 0.056 Uiso 1 1 calc R . . C28 C 1.0411(2) 0.1796(6) 0.4276(2) 0.0377(12) Uani 1 1 d . . . H28 H 1.0111 0.0914 0.4264 0.045 Uiso 1 1 calc R . . C29 C 0.7371(2) 0.0708(5) 0.3315(2) 0.0294(11) Uani 1 1 d . . . C30 C 0.6777(2) -0.0005(5) 0.3404(2) 0.0354(12) Uani 1 1 d . . . H30 H 0.6410 -0.0202 0.3099 0.042 Uiso 1 1 calc R . . C32 C 0.7415(2) 0.0114(5) 0.4326(2) 0.0332(12) Uani 1 1 d . . . C33 C 0.7651(2) 0.0031(6) 0.4939(2) 0.0421(13) Uani 1 1 d . . . H33 H 0.7403 -0.0479 0.5200 0.050 Uiso 1 1 calc R . . C34 C 0.8268(3) 0.0730(6) 0.5156(2) 0.0462(14) Uani 1 1 d . . . H34 H 0.8437 0.0716 0.5571 0.055 Uiso 1 1 calc R . . C35 C 0.8646(2) 0.1465(6) 0.4756(2) 0.0451(13) Uani 1 1 d . . . H35 H 0.9062 0.1927 0.4910 0.054 Uiso 1 1 calc R . . C36 C 0.8410(2) 0.1512(6) 0.4142(2) 0.0357(12) Uani 1 1 d . . . H36 H 0.8663 0.2002 0.3881 0.043 Uiso 1 1 calc R . . C37 C 0.7785(2) 0.0815(5) 0.3913(2) 0.0316(11) Uani 1 1 d . . . C38 C 0.6268(2) -0.1166(5) 0.4252(2) 0.0404(13) Uani 1 1 d . . . H38A H 0.5858 -0.1091 0.3955 0.048 Uiso 1 1 calc R . . H38B H 0.6201 -0.0540 0.4608 0.048 Uiso 1 1 calc R . . C39 C 0.6387(2) -0.2975(6) 0.44302(19) 0.0326(12) Uani 1 1 d . . . C42 C 0.6509(2) -0.6357(6) 0.4726(2) 0.0418(13) Uani 1 1 d . . . H42 H 0.6547 -0.7490 0.4819 0.050 Uiso 1 1 calc R . . C43 C 0.5928(2) -0.5514(6) 0.4762(2) 0.0442(13) Uani 1 1 d . . . H43 H 0.5573 -0.6072 0.4886 0.053 Uiso 1 1 calc R . . C44 C 0.5872(2) -0.3849(6) 0.4617(2) 0.0374(12) Uani 1 1 d . . . H44 H 0.5476 -0.3292 0.4644 0.045 Uiso 1 1 calc R . . C50 C 0.5960(3) 0.4840(8) 0.2985(3) 0.0787(19) Uani 1 1 d . . . H50A H 0.5879 0.3770 0.2781 0.094 Uiso 1 1 calc R . . H50B H 0.6018 0.4643 0.3419 0.094 Uiso 1 1 calc R . . C40 C 0.6974(2) -0.3826(6) 0.4407(2) 0.0421(13) Uani 1 1 d . . . H40 H 0.7333 -0.3264 0.4292 0.051 Uiso 1 1 calc R . . C41 C 0.7034(2) -0.5516(6) 0.4551(2) 0.0461(13) Uani 1 1 d . . . H41 H 0.7430 -0.6078 0.4530 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1694(19) 0.0832(14) 0.0768(13) -0.0241(10) 0.0591(13) -0.0434(13) Cl2 0.168(2) 0.200(3) 0.163(2) -0.013(2) -0.0140(19) 0.110(2) F8 0.0370(16) 0.0411(18) 0.072(2) -0.0110(15) 0.0059(14) -0.0070(14) F9 0.066(2) 0.0337(19) 0.091(2) -0.0108(17) 0.0055(17) -0.0072(16) F10 0.072(2) 0.041(2) 0.101(3) 0.0042(18) 0.0072(18) 0.0161(18) F11 0.042(2) 0.056(2) 0.186(4) 0.019(2) -0.008(2) 0.0092(17) F12 0.0412(17) 0.041(2) 0.133(3) 0.0119(19) -0.0172(18) -0.0086(15) O1 0.0359(18) 0.035(2) 0.0338(19) 0.0040(15) 0.0104(15) 0.0010(15) O2 0.0298(19) 0.046(2) 0.042(2) 0.0032(16) 0.0071(15) 0.0004(16) N1 0.029(2) 0.027(2) 0.030(2) 0.0070(18) 0.0037(17) -0.0001(17) N15 0.029(2) 0.031(2) 0.030(2) 0.0051(19) 0.0038(17) 0.0032(19) N31 0.041(2) 0.030(2) 0.042(3) 0.005(2) 0.018(2) 0.001(2) C2 0.029(3) 0.027(3) 0.034(3) -0.009(2) 0.009(2) -0.004(2) C3 0.034(3) 0.024(3) 0.026(3) 0.006(2) 0.003(2) -0.004(2) C4 0.037(3) 0.022(3) 0.028(3) 0.004(2) 0.005(2) 0.001(2) C5 0.037(3) 0.021(3) 0.034(3) -0.007(2) 0.008(2) -0.003(2) C6 0.032(3) 0.026(3) 0.031(3) 0.003(2) 0.001(2) -0.004(2) C7 0.029(3) 0.032(3) 0.028(3) 0.005(2) 0.003(2) 0.000(2) C8 0.029(3) 0.041(4) 0.036(3) -0.002(3) 0.006(2) -0.007(3) C9 0.059(4) 0.025(3) 0.041(3) -0.005(3) 0.005(3) -0.005(3) C10 0.051(3) 0.032(4) 0.052(3) 0.007(3) -0.001(3) 0.009(3) C11 0.033(3) 0.053(4) 0.078(4) 0.005(3) -0.007(3) 0.000(3) C12 0.041(3) 0.033(3) 0.061(4) 0.009(3) -0.002(3) -0.005(3) C13 0.026(3) 0.030(3) 0.032(3) -0.001(2) 0.008(2) 0.001(2) C14 0.041(3) 0.031(3) 0.022(3) 0.003(2) 0.006(2) 0.006(2) C16 0.043(3) 0.026(3) 0.022(3) 0.000(2) 0.009(2) 0.002(2) C17 0.038(3) 0.040(3) 0.025(3) 0.006(2) 0.008(2) 0.011(3) C18 0.056(3) 0.035(3) 0.041(3) 0.007(3) 0.014(3) 0.008(3) C19 0.046(3) 0.035(3) 0.051(3) 0.002(3) 0.017(3) -0.004(3) C20 0.035(3) 0.029(3) 0.046(3) 0.007(3) 0.010(2) 0.006(2) C21 0.035(3) 0.027(3) 0.025(3) -0.001(2) 0.008(2) 0.006(2) C22 0.030(3) 0.040(3) 0.040(3) 0.005(3) 0.010(2) 0.004(2) C23 0.028(3) 0.032(3) 0.035(3) 0.002(2) 0.003(2) 0.009(2) C24 0.041(3) 0.040(3) 0.042(3) 0.009(3) 0.004(2) -0.003(3) C25 0.067(4) 0.040(3) 0.051(4) -0.002(3) 0.008(3) -0.014(3) C26 0.069(4) 0.041(4) 0.043(3) -0.008(3) 0.004(3) -0.005(3) C27 0.056(3) 0.046(4) 0.037(3) -0.004(3) 0.009(3) -0.002(3) C28 0.039(3) 0.034(3) 0.040(3) 0.004(3) 0.008(2) -0.002(2) C29 0.030(3) 0.020(3) 0.039(3) 0.002(2) 0.011(2) 0.003(2) C30 0.041(3) 0.029(3) 0.037(3) 0.000(2) 0.011(2) 0.006(2) C32 0.041(3) 0.027(3) 0.034(3) 0.004(2) 0.013(2) 0.007(2) C33 0.048(3) 0.039(3) 0.043(3) 0.003(3) 0.017(3) 0.010(3) C34 0.061(4) 0.048(4) 0.031(3) -0.003(3) 0.010(3) 0.013(3) C35 0.048(3) 0.042(3) 0.046(3) -0.006(3) 0.010(3) 0.004(3) C36 0.044(3) 0.032(3) 0.034(3) -0.002(2) 0.015(2) 0.001(2) C37 0.040(3) 0.023(3) 0.035(3) 0.005(2) 0.014(2) 0.002(2) C38 0.041(3) 0.032(3) 0.055(3) 0.006(3) 0.027(2) 0.002(2) C39 0.033(3) 0.031(3) 0.035(3) 0.000(2) 0.013(2) 0.000(2) C42 0.061(3) 0.021(3) 0.042(3) 0.003(2) 0.005(3) -0.002(3) C43 0.053(3) 0.035(4) 0.048(3) 0.008(3) 0.021(3) -0.003(3) C44 0.034(3) 0.034(3) 0.045(3) 0.004(3) 0.008(2) 0.002(2) C50 0.088(5) 0.088(5) 0.065(4) -0.006(4) 0.027(4) 0.003(4) C40 0.035(3) 0.034(3) 0.062(4) 0.001(3) 0.022(2) -0.003(3) C41 0.049(3) 0.033(4) 0.057(4) -0.001(3) 0.013(3) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C50 1.766(5) . ? Cl2 C50 1.720(6) . ? F8 C8 1.352(5) . ? F9 C9 1.343(5) . ? F10 C10 1.334(5) . ? F11 C11 1.344(5) . ? F12 C12 1.345(5) . ? O1 C2 1.223(4) . ? O2 C5 1.216(5) . ? N1 C2 1.380(5) . ? N1 C5 1.393(5) . ? N1 C6 1.448(5) . ? N15 C14 1.358(5) . ? N15 C16 1.403(5) . ? N15 C22 1.451(5) . ? N31 C30 1.360(5) . ? N31 C32 1.379(5) . ? N31 C38 1.452(5) . ? C2 C3 1.492(6) . ? C3 C4 1.352(5) . ? C3 C13 1.435(6) . ? C4 C29 1.434(6) . ? C4 C5 1.489(6) . ? C6 C7 1.505(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.367(6) . ? C7 C8 1.372(6) . ? C8 C9 1.362(6) . ? C9 C10 1.367(6) . ? C10 C11 1.365(7) . ? C11 C12 1.372(7) . ? C13 C14 1.372(5) . ? C13 C21 1.454(6) . ? C14 H14 0.9300 . ? C16 C17 1.392(6) . ? C16 C21 1.417(5) . ? C17 C18 1.371(6) . ? C17 H17 0.9300 . ? C18 C19 1.404(6) . ? C18 H18 0.9300 . ? C19 C20 1.375(6) . ? C19 H19 0.9300 . ? C20 C21 1.397(6) . ? C20 H20 0.9300 . ? C22 C23 1.509(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.388(6) . ? C23 C28 1.391(6) . ? C24 C25 1.376(6) . ? C24 H24 0.9300 . ? C25 C26 1.375(6) . ? C25 H25 0.9300 . ? C26 C27 1.365(6) . ? C26 H26 0.9300 . ? C27 C28 1.373(6) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.378(5) . ? C29 C37 1.449(6) . ? C30 H30 0.9300 . ? C32 C33 1.372(6) . ? C32 C37 1.405(5) . ? C33 C34 1.378(6) . ? C33 H33 0.9300 . ? C34 C35 1.406(6) . ? C34 H34 0.9300 . ? C35 C36 1.372(6) . ? C35 H35 0.9300 . ? C36 C37 1.396(6) . ? C36 H36 0.9300 . ? C38 C39 1.509(6) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.380(6) . ? C39 C44 1.383(5) . ? C42 C43 1.372(6) . ? C42 C41 1.375(6) . ? C42 H42 0.9300 . ? C43 C44 1.372(6) . ? C43 H43 0.9300 . ? C44 H44 0.9300 . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C40 C41 1.390(6) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? 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 N1 C5 109.7(4) . . ? C2 N1 C6 125.1(3) . . ? C5 N1 C6 123.2(3) . . ? C14 N15 C16 108.2(3) . . ? C14 N15 C22 124.2(4) . . ? C16 N15 C22 126.9(4) . . ? C30 N31 C32 109.1(4) . . ? C30 N31 C38 125.1(4) . . ? C32 N31 C38 125.9(4) . . ? O1 C2 N1 124.3(4) . . ? O1 C2 C3 128.2(4) . . ? N1 C2 C3 107.5(3) . . ? C4 C3 C13 131.1(4) . . ? C4 C3 C2 107.5(4) . . ? C13 C3 C2 121.0(3) . . ? C3 C4 C29 130.3(4) . . ? C3 C4 C5 108.2(4) . . ? C29 C4 C5 121.4(4) . . ? O2 C5 N1 123.8(4) . . ? O2 C5 C4 129.5(4) . . ? N1 C5 C4 106.8(3) . . ? N1 C6 C7 113.2(4) . . ? N1 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? N1 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C12 C7 C8 115.7(4) . . ? C12 C7 C6 122.0(4) . . ? C8 C7 C6 122.3(4) . . ? F8 C8 C9 118.3(4) . . ? F8 C8 C7 118.5(4) . . ? C9 C8 C7 123.2(4) . . ? F9 C9 C8 120.3(5) . . ? F9 C9 C10 119.8(5) . . ? C8 C9 C10 119.9(5) . . ? F10 C10 C11 121.1(5) . . ? F10 C10 C9 120.5(5) . . ? C11 C10 C9 118.4(5) . . ? F11 C11 C10 119.2(5) . . ? F11 C11 C12 120.3(5) . . ? C10 C11 C12 120.5(5) . . ? F12 C12 C7 120.2(5) . . ? F12 C12 C11 117.6(4) . . ? C7 C12 C11 122.2(5) . . ? C14 C13 C3 128.2(4) . . ? C14 C13 C21 105.1(4) . . ? C3 C13 C21 126.6(4) . . ? N15 C14 C13 112.1(4) . . ? N15 C14 H14 123.9 . . ? C13 C14 H14 123.9 . . ? C17 C16 N15 130.6(4) . . ? C17 C16 C21 122.2(4) . . ? N15 C16 C21 107.1(4) . . ? C18 C17 C16 117.6(4) . . ? C18 C17 H17 121.2 . . ? C16 C17 H17 121.2 . . ? C17 C18 C19 121.0(5) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 121.7(5) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C19 C20 C21 118.7(4) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C16 118.8(4) . . ? C20 C21 C13 133.7(4) . . ? C16 C21 C13 107.4(4) . . ? N15 C22 C23 112.8(3) . . ? N15 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? N15 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C24 C23 C28 117.8(4) . . ? C24 C23 C22 120.2(4) . . ? C28 C23 C22 121.9(4) . . ? C25 C24 C23 120.7(4) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C26 C25 C24 120.4(5) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C27 C26 C25 119.6(5) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C28 120.5(5) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C23 120.9(5) . . ? C27 C28 H28 119.5 . . ? C23 C28 H28 119.5 . . ? C30 C29 C4 125.4(4) . . ? C30 C29 C37 105.6(4) . . ? C4 C29 C37 129.0(4) . . ? N31 C30 C29 110.6(4) . . ? N31 C30 H30 124.7 . . ? C29 C30 H30 124.7 . . ? C33 C32 N31 129.2(4) . . ? C33 C32 C37 123.0(4) . . ? N31 C32 C37 107.7(4) . . ? C32 C33 C34 117.7(4) . . ? C32 C33 H33 121.2 . . ? C34 C33 H33 121.2 . . ? C33 C34 C35 120.7(5) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.7 . . ? C36 C35 C34 121.1(5) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C35 C36 C37 119.2(4) . . ? C35 C36 H36 120.4 . . ? C37 C36 H36 120.4 . . ? C36 C37 C32 118.4(4) . . ? C36 C37 C29 134.5(4) . . ? C32 C37 C29 107.0(4) . . ? N31 C38 C39 115.0(3) . . ? N31 C38 H38A 108.5 . . ? C39 C38 H38A 108.5 . . ? N31 C38 H38B 108.5 . . ? C39 C38 H38B 108.5 . . ? H38A C38 H38B 107.5 . . ? C40 C39 C44 117.7(4) . . ? C40 C39 C38 124.2(4) . . ? C44 C39 C38 118.1(4) . . ? C43 C42 C41 119.6(5) . . ? C43 C42 H42 120.2 . . ? C41 C42 H42 120.2 . . ? C44 C43 C42 119.9(4) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C43 C44 C39 121.9(4) . . ? C43 C44 H44 119.1 . . ? C39 C44 H44 119.1 . . ? Cl2 C50 Cl1 112.1(4) . . ? Cl2 C50 H50A 109.2 . . ? Cl1 C50 H50A 109.2 . . ? Cl2 C50 H50B 109.2 . . ? Cl1 C50 H50B 109.2 . . ? H50A C50 H50B 107.9 . . ? C39 C40 C41 120.8(4) . . ? C39 C40 H40 119.6 . . ? C41 C40 H40 119.6 . . ? C42 C41 C40 120.1(4) . . ? C42 C41 H41 119.9 . . ? C40 C41 H41 119.9 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.365 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.066