# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Stephen Barlow' 'Mikhail Yu Antipin' 'Jean-Luc Bredas' 'Veaceslav Coropceanu' 'Simon C. Jones' 'Victor Khrustalev' 'Tiffany L. Kinnibrugh' 'Zerubba Levi' 'Seth R. Marder' 'Chad Risko' 'Neil M. Tucker' _publ_contact_author_name ' Stephen Barlow ' _publ_contact_author_address ; School of Chemistry and Biochemistry Georgia Institute of Technology 770 State Street Atlanta GA 30332-0400 UNITED STATES OF AMERICA ; _publ_contact_author_email ' stephen.barlow@chemistry.gatech.edu' _publ_contact_author_fax ' (404)385-6057' _publ_contact_author_phone ' (404)385-6053' _publ_section_title ; A mixed-valence bis(diarylamino)stilbene: crystal structure and comparison of electronic coupling with biphenyl and tolane analogues ; _publ_section_references ; Bruker (1998a) SAINTPlus Data Reduction and Correction Program v. 6.01, Bruker AXS, Madison, Wisconsin, USA. Bruker (1998b) SMART. Bruker Molecular Analysis Research Tool, v. 5.059. Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (1998a). SADABS v.2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (1998b). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; data_COMPOUND_4 _database_code_depnum_ccdc_archive 'CCDC 252359' _audit_creation_method SHELXL-97 _chemical_name_systematic ; E-4,4'-Bis[4-bis(4-methoxyphenyl)amino]stilbene ; _chemical_melting_point 'not measured' _chemical_formula_moiety 'C42 H38 N2 O4' _chemical_formula_sum 'C42 H38 N2 O4' _chemical_formula_weight 634.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(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 10.788(3) _cell_length_b 12.557(3) _cell_length_c 12.734(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.886(6) _cell_angle_gamma 90.00 _cell_volume 1659.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 710 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.65 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 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 12024 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.21 _reflns_number_total 4027 _reflns_number_gt 1907 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998b)' _computing_cell_refinement 'SAINTPlus (Bruker, 1998a)' _computing_data_reduction 'SAINTPlus (Bruker, 1998a)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0314P)^2^+0.6500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4027 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1148 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.24781(16) 0.94160(13) 0.09034(14) 0.0439(4) Uani 1 1 d . . . O1 O 0.42098(15) 1.14729(13) 0.49220(12) 0.0582(4) Uani 1 1 d . . . O2 O 0.19587(15) 1.20496(12) -0.27111(12) 0.0552(4) Uani 1 1 d . . . C1 C 0.03687(19) 0.52399(17) 0.04483(17) 0.0403(5) Uani 1 1 d . . . H1 H 0.0576(18) 0.4825(15) 0.1083(16) 0.044(6) Uiso 1 1 d . . . C2 C 0.09607(19) 0.62819(16) 0.05301(16) 0.0384(5) Uani 1 1 d . . . C3 C 0.0819(2) 0.69719(17) -0.03646(18) 0.0401(5) Uani 1 1 d . . . H3 H 0.0269(17) 0.6749(14) -0.1143(16) 0.038(5) Uiso 1 1 d . . . C4 C 0.13275(19) 0.79854(17) -0.02435(18) 0.0399(5) Uani 1 1 d . . . H4 H 0.1207(17) 0.8477(15) -0.0892(15) 0.037(5) Uiso 1 1 d . . . C5 C 0.20111(19) 0.83790(16) 0.07845(17) 0.0412(5) Uani 1 1 d . . . C6 C 0.2203(2) 0.76808(17) 0.16679(19) 0.0442(5) Uani 1 1 d . . . H6 H 0.2708(19) 0.7920(16) 0.2351(17) 0.049(6) Uiso 1 1 d . . . C7 C 0.1681(2) 0.66697(17) 0.15369(19) 0.0437(5) Uani 1 1 d . . . H7 H 0.1830(16) 0.6181(14) 0.2183(14) 0.030(5) Uiso 1 1 d . . . C8 C 0.2925(2) 0.99287(16) 0.19429(17) 0.0422(5) Uani 1 1 d . . . C9 C 0.2201(2) 0.99478(18) 0.26939(18) 0.0483(6) Uani 1 1 d . . . H9 H 0.1387(19) 0.9598(15) 0.2534(15) 0.041(6) Uiso 1 1 d . . . C10 C 0.2663(2) 1.04632(18) 0.36796(19) 0.0503(6) Uani 1 1 d . . . H10 H 0.210(2) 1.0467(16) 0.4215(17) 0.059(6) Uiso 1 1 d . . . C11 C 0.3843(2) 1.09784(17) 0.39259(17) 0.0440(5) Uani 1 1 d . . . C12 C 0.4557(2) 1.09832(18) 0.31810(19) 0.0473(6) Uani 1 1 d . . . H12 H 0.5365(19) 1.1367(16) 0.3297(15) 0.045(6) Uiso 1 1 d . . . C13 C 0.4084(2) 1.04587(17) 0.21949(19) 0.0458(5) Uani 1 1 d . . . H13 H 0.4529(18) 1.0488(15) 0.1648(16) 0.042(6) Uiso 1 1 d . . . C14 C 0.2363(2) 1.00794(16) -0.00386(16) 0.0399(5) Uani 1 1 d . . . C15 C 0.3185(2) 0.99691(17) -0.06827(18) 0.0466(6) Uani 1 1 d . . . H15 H 0.3911(18) 0.9429(16) -0.0496(15) 0.042(6) Uiso 1 1 d . . . C16 C 0.3072(2) 1.06108(17) -0.15898(18) 0.0447(5) Uani 1 1 d . . . H16 H 0.3682(18) 1.0509(15) -0.2076(15) 0.044(6) Uiso 1 1 d . . . C17 C 0.2141(2) 1.13935(16) -0.18363(17) 0.0414(5) Uani 1 1 d . . . C18 C 0.1312(2) 1.15174(19) -0.11809(19) 0.0496(6) Uani 1 1 d . . . H18 H 0.0662(19) 1.2059(16) -0.1387(16) 0.049(6) Uiso 1 1 d . . . C19 C 0.1431(2) 1.08676(19) -0.02938(19) 0.0499(6) Uani 1 1 d . . . H19 H 0.076(2) 1.0921(16) 0.0164(17) 0.054(6) Uiso 1 1 d . . . C20 C 0.2754(3) 1.1891(2) -0.3424(2) 0.0566(7) Uani 1 1 d . . . H20C H 0.366(2) 1.2062(16) -0.3053(16) 0.050(6) Uiso 1 1 d . . . H20B H 0.237(2) 1.2449(18) -0.4062(19) 0.065(7) Uiso 1 1 d . . . H20A H 0.262(2) 1.116(2) -0.372(2) 0.077(8) Uiso 1 1 d . . . C21 C 0.5375(3) 1.2055(3) 0.5173(3) 0.0647(8) Uani 1 1 d . . . H21C H 0.533(2) 1.258(2) 0.462(2) 0.070(8) Uiso 1 1 d . . . H21B H 0.612(3) 1.156(2) 0.519(2) 0.086(9) Uiso 1 1 d . . . H21A H 0.549(2) 1.238(2) 0.589(2) 0.090(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0575(11) 0.0364(10) 0.0394(11) -0.0055(8) 0.0159(9) -0.0091(9) O1 0.0649(10) 0.0603(11) 0.0464(10) -0.0084(8) 0.0102(8) -0.0183(9) O2 0.0710(11) 0.0463(10) 0.0446(9) 0.0075(7) 0.0094(8) 0.0036(8) C1 0.0435(13) 0.0361(12) 0.0422(14) 0.0000(10) 0.0131(10) 0.0084(10) C2 0.0397(12) 0.0364(12) 0.0409(13) -0.0015(10) 0.0139(10) 0.0040(10) C3 0.0388(12) 0.0403(13) 0.0415(13) -0.0026(10) 0.0115(10) 0.0052(10) C4 0.0425(12) 0.0373(12) 0.0415(13) 0.0013(10) 0.0143(10) 0.0023(10) C5 0.0421(12) 0.0383(13) 0.0458(14) -0.0025(10) 0.0162(10) 0.0001(10) C6 0.0487(14) 0.0418(14) 0.0389(13) -0.0027(11) 0.0066(11) 0.0002(11) C7 0.0511(13) 0.0375(13) 0.0420(14) 0.0049(10) 0.0120(11) 0.0062(11) C8 0.0510(13) 0.0364(12) 0.0401(13) -0.0020(9) 0.0140(10) -0.0020(10) C9 0.0498(14) 0.0504(14) 0.0480(14) -0.0060(11) 0.0188(11) -0.0166(12) C10 0.0585(15) 0.0524(15) 0.0464(15) -0.0057(11) 0.0252(12) -0.0136(12) C11 0.0510(13) 0.0409(13) 0.0388(13) -0.0013(10) 0.0099(10) -0.0063(11) C12 0.0406(13) 0.0458(14) 0.0542(15) -0.0009(11) 0.0106(11) -0.0073(11) C13 0.0434(13) 0.0498(14) 0.0472(14) -0.0027(11) 0.0178(11) -0.0005(11) C14 0.0480(13) 0.0327(12) 0.0394(13) -0.0039(9) 0.0127(10) -0.0032(10) C15 0.0532(14) 0.0382(13) 0.0511(15) 0.0055(10) 0.0188(11) 0.0092(11) C16 0.0520(13) 0.0419(13) 0.0441(13) 0.0031(10) 0.0195(11) 0.0045(11) C17 0.0478(13) 0.0352(12) 0.0379(12) -0.0042(9) 0.0061(10) -0.0033(10) C18 0.0475(14) 0.0462(14) 0.0502(15) -0.0022(11) 0.0048(11) 0.0124(12) C19 0.0475(13) 0.0564(15) 0.0481(15) -0.0060(12) 0.0171(11) 0.0053(12) C20 0.0702(19) 0.0537(17) 0.0446(15) 0.0058(13) 0.0138(14) -0.0104(15) C21 0.068(2) 0.065(2) 0.0513(19) -0.0082(15) 0.0000(14) -0.0198(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 N1 C5 1.389(2) . ? N1 C8 1.432(3) . ? N1 C14 1.438(3) . ? O1 C11 1.370(2) . ? O1 C21 1.413(3) . ? O2 C17 1.356(2) . ? O2 C20 1.423(3) . ? C1 C1 1.343(4) 3_565 ? C1 C2 1.447(3) . ? C1 H1 0.936(19) . ? C2 C7 1.393(3) . ? C2 C3 1.406(3) . ? C3 C4 1.378(3) . ? C3 H3 1.044(19) . ? C4 C5 1.405(3) . ? C4 H4 1.010(18) . ? C5 C6 1.396(3) . ? C6 C7 1.380(3) . ? C6 H6 0.94(2) . ? C7 H7 1.004(17) . ? C8 C13 1.374(3) . ? C8 C9 1.391(3) . ? C9 C10 1.378(3) . ? C9 H9 0.953(19) . ? C10 C11 1.386(3) . ? C10 H10 1.03(2) . ? C11 C12 1.376(3) . ? C12 C13 1.386(3) . ? C12 H12 0.97(2) . ? C13 H13 0.948(19) . ? C14 C15 1.370(3) . ? C14 C19 1.385(3) . ? C15 C16 1.386(3) . ? C15 H15 1.01(2) . ? C16 C17 1.378(3) . ? C16 H16 1.027(19) . ? C17 C18 1.389(3) . ? C18 C19 1.371(3) . ? C18 H18 0.96(2) . ? C19 H19 1.05(2) . ? C20 H20C 0.99(2) . ? C20 H20B 1.07(2) . ? C20 H20A 0.99(3) . ? C21 H21C 0.96(3) . ? C21 H21B 1.01(3) . ? C21 H21A 0.98(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 C5 N1 C8 122.86(17) . . ? C5 N1 C14 120.40(17) . . ? C8 N1 C14 116.18(16) . . ? C11 O1 C21 117.2(2) . . ? C17 O2 C20 117.47(19) . . ? C1 C1 C2 127.9(3) 3_565 . ? C1 C1 H1 115.5(12) 3_565 . ? C2 C1 H1 116.4(12) . . ? C7 C2 C3 116.1(2) . . ? C7 C2 C1 120.43(19) . . ? C3 C2 C1 123.43(19) . . ? C4 C3 C2 121.8(2) . . ? C4 C3 H3 117.3(10) . . ? C2 C3 H3 120.8(10) . . ? C3 C4 C5 121.4(2) . . ? C3 C4 H4 121.0(11) . . ? C5 C4 H4 117.6(11) . . ? N1 C5 C6 122.08(19) . . ? N1 C5 C4 120.90(19) . . ? C6 C5 C4 117.0(2) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 121.3(13) . . ? C5 C6 H6 117.7(13) . . ? C6 C7 C2 122.6(2) . . ? C6 C7 H7 119.7(10) . . ? C2 C7 H7 117.7(10) . . ? C13 C8 C9 118.5(2) . . ? C13 C8 N1 119.24(19) . . ? C9 C8 N1 122.20(19) . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.5(12) . . ? C8 C9 H9 120.3(11) . . ? C9 C10 C11 120.4(2) . . ? C9 C10 H10 118.4(12) . . ? C11 C10 H10 121.2(12) . . ? O1 C11 C12 124.2(2) . . ? O1 C11 C10 115.85(19) . . ? C12 C11 C10 120.0(2) . . ? C11 C12 C13 119.1(2) . . ? C11 C12 H12 123.1(12) . . ? C13 C12 H12 117.8(12) . . ? C8 C13 C12 121.9(2) . . ? C8 C13 H13 117.3(12) . . ? C12 C13 H13 120.8(12) . . ? C15 C14 C19 118.7(2) . . ? C15 C14 N1 121.23(19) . . ? C19 C14 N1 120.09(19) . . ? C14 C15 C16 121.1(2) . . ? C14 C15 H15 120.8(11) . . ? C16 C15 H15 118.1(11) . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 119.9(11) . . ? C15 C16 H16 120.3(11) . . ? O2 C17 C16 123.60(19) . . ? O2 C17 C18 116.9(2) . . ? C16 C17 C18 119.5(2) . . ? C19 C18 C17 119.9(2) . . ? C19 C18 H18 122.9(12) . . ? C17 C18 H18 117.2(12) . . ? C18 C19 C14 121.1(2) . . ? C18 C19 H19 119.9(11) . . ? C14 C19 H19 118.8(11) . . ? O2 C20 H20C 111.0(12) . . ? O2 C20 H20B 102.7(12) . . ? H20C C20 H20B 110.3(17) . . ? O2 C20 H20A 108.9(14) . . ? H20C C20 H20A 114.2(19) . . ? H20B C20 H20A 109.2(18) . . ? O1 C21 H21C 109.1(15) . . ? O1 C21 H21B 109.7(15) . . ? H21C C21 H21B 109(2) . . ? O1 C21 H21A 107.8(16) . . ? H21C C21 H21A 112(2) . . ? H21B C21 H21A 110(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C7 178.7(3) 3_565 . . . ? C1 C1 C2 C3 0.9(4) 3_565 . . . ? C7 C2 C3 C4 -2.1(3) . . . . ? C1 C2 C3 C4 175.70(18) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C8 N1 C5 C6 -14.5(3) . . . . ? C14 N1 C5 C6 174.33(19) . . . . ? C8 N1 C5 C4 165.96(19) . . . . ? C14 N1 C5 C4 -5.2(3) . . . . ? C3 C4 C5 N1 -177.57(18) . . . . ? C3 C4 C5 C6 2.9(3) . . . . ? N1 C5 C6 C7 177.11(19) . . . . ? C4 C5 C6 C7 -3.4(3) . . . . ? C5 C6 C7 C2 1.1(3) . . . . ? C3 C2 C7 C6 1.7(3) . . . . ? C1 C2 C7 C6 -176.24(19) . . . . ? C5 N1 C8 C13 132.4(2) . . . . ? C14 N1 C8 C13 -56.2(3) . . . . ? C5 N1 C8 C9 -50.4(3) . . . . ? C14 N1 C8 C9 121.1(2) . . . . ? C13 C8 C9 C10 -1.9(3) . . . . ? N1 C8 C9 C10 -179.1(2) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C21 O1 C11 C12 2.4(3) . . . . ? C21 O1 C11 C10 -176.6(2) . . . . ? C9 C10 C11 O1 179.5(2) . . . . ? C9 C10 C11 C12 0.5(4) . . . . ? O1 C11 C12 C13 -179.7(2) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C9 C8 C13 C12 1.7(3) . . . . ? N1 C8 C13 C12 179.0(2) . . . . ? C11 C12 C13 C8 -0.4(3) . . . . ? C5 N1 C14 C15 -78.5(3) . . . . ? C8 N1 C14 C15 109.8(2) . . . . ? C5 N1 C14 C19 103.3(2) . . . . ? C8 N1 C14 C19 -68.4(3) . . . . ? C19 C14 C15 C16 -1.7(3) . . . . ? N1 C14 C15 C16 -179.9(2) . . . . ? C14 C15 C16 C17 1.8(3) . . . . ? C20 O2 C17 C16 1.9(3) . . . . ? C20 O2 C17 C18 -176.5(2) . . . . ? C15 C16 C17 O2 -179.5(2) . . . . ? C15 C16 C17 C18 -1.1(3) . . . . ? O2 C17 C18 C19 178.9(2) . . . . ? C16 C17 C18 C19 0.4(3) . . . . ? C17 C18 C19 C14 -0.4(3) . . . . ? C15 C14 C19 C18 1.0(3) . . . . ? N1 C14 C19 C18 179.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.204 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.045 #===END data_COMPOUND_4_SBF6 _database_code_depnum_ccdc_archive 'CCDC 252360' _audit_creation_method SHELXL-97 _chemical_name_systematic ; E-4,4'-Bis[4-bis(4-methoxyphenyl)amino]stilbene ; _chemical_melting_point 'not measured' _chemical_formula_moiety 'C42 H38 N2 O4 1+, F6 Sb 1-' _chemical_formula_sum 'C42 H38 F6 N2 O4 Sb' _chemical_formula_weight 870.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 10.5478(10) _cell_length_b 35.449(3) _cell_length_c 11.1632(11) _cell_angle_alpha 90.00 _cell_angle_beta 116.442(2) _cell_angle_gamma 90.00 _cell_volume 3737.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7947 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 29.9 _exptl_crystal_description plate _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1764 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7923 _exptl_absorpt_correction_T_max 0.9377 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 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 43844 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -49 _diffrn_reflns_limit_k_max 50 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 30.19 _reflns_number_total 10983 _reflns_number_gt 8265 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998b)' _computing_cell_refinement 'SAINTPlus (Bruker, 1998a)' _computing_data_reduction 'SAINTPlus (Bruker, 1998a)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0700P)^2^+7.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10983 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1520 _refine_ls_wR_factor_gt 0.1433 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Sb1 Sb 0.72117(2) 0.117693(7) 0.11448(2) 0.03633(8) Uani 1 1 d . . . F1 F 0.8522(3) 0.11416(9) 0.2939(3) 0.0645(8) Uani 1 1 d . . . F2 F 0.5887(3) 0.12125(8) -0.0636(3) 0.0615(7) Uani 1 1 d . . . F3 F 0.6592(3) 0.16406(7) 0.1486(3) 0.0623(7) Uani 1 1 d . . . F4 F 0.5856(3) 0.09393(7) 0.1539(3) 0.0583(6) Uani 1 1 d . . . F5 F 0.7766(2) 0.07086(6) 0.0776(2) 0.0456(5) Uani 1 1 d . . . F6 F 0.8543(3) 0.14184(7) 0.0752(3) 0.0551(6) Uani 1 1 d . . . O1 O 1.2143(3) 0.04543(8) 1.4127(2) 0.0447(6) Uani 1 1 d . . . O2 O 1.4717(3) -0.00260(9) 0.7177(3) 0.0541(7) Uani 1 1 d . . . O3 O -0.2846(3) 0.31678(8) 0.2180(3) 0.0487(7) Uani 1 1 d . . . O4 O -0.1058(3) 0.23074(8) -0.4708(2) 0.0405(6) Uani 1 1 d . . . N1 N 1.0759(3) 0.05460(8) 0.8711(3) 0.0320(6) Uani 1 1 d . . . N2 N 0.0340(3) 0.21910(8) 0.0709(3) 0.0325(6) Uani 1 1 d . . . C1 C 0.5598(5) 0.12647(13) 0.5227(5) 0.0531(10) Uani 1 1 d . . . H1 H 0.5033 0.1335 0.5656 0.064 Uiso 1 1 calc R . . C2 C 0.6953(4) 0.10629(11) 0.6028(4) 0.0484(10) Uani 1 1 d . . . C3 C 0.8037(5) 0.09861(11) 0.5658(4) 0.0515(11) Uani 1 1 d . . . H3 H 0.7899 0.1054 0.4785 0.062 Uiso 1 1 calc R . . C4 C 0.9303(4) 0.08155(10) 0.6518(3) 0.0401(8) Uani 1 1 d . . . H4 H 1.0019 0.0771 0.6239 0.048 Uiso 1 1 calc R . . C5 C 0.9512(4) 0.07096(9) 0.7812(3) 0.0327(6) Uani 1 1 d . . . C6 C 0.8402(4) 0.07778(10) 0.8169(4) 0.0363(7) Uani 1 1 d . . . H6 H 0.8507 0.0702 0.9025 0.044 Uiso 1 1 calc R . . C7 C 0.7178(4) 0.09511(11) 0.7293(4) 0.0453(9) Uani 1 1 d . . . H7 H 0.6457 0.0996 0.7566 0.054 Uiso 1 1 calc R . . C8 C 1.1133(3) 0.05352(9) 1.0104(3) 0.0306(6) Uani 1 1 d . . . C9 C 1.0986(3) 0.08517(9) 1.0760(3) 0.0329(7) Uani 1 1 d . . . H9 H 1.0657 0.1081 1.0281 0.040 Uiso 1 1 calc R . . C10 C 1.1314(4) 0.08369(10) 1.2105(3) 0.0345(7) Uani 1 1 d . . . H10 H 1.1205 0.1054 1.2548 0.041 Uiso 1 1 calc R . . C11 C 1.1803(4) 0.05014(10) 1.2798(3) 0.0349(7) Uani 1 1 d . . . C12 C 1.1991(4) 0.01879(10) 1.2156(3) 0.0375(7) Uani 1 1 d . . . H12 H 1.2351 -0.0039 1.2643 0.045 Uiso 1 1 calc R . . C13 C 1.1662(4) 0.02018(10) 1.0821(3) 0.0342(7) Uani 1 1 d . . . H13 H 1.1794 -0.0014 1.0387 0.041 Uiso 1 1 calc R . . C14 C 1.1738(4) 0.03847(10) 0.8296(3) 0.0349(7) Uani 1 1 d . . . C15 C 1.1326(4) 0.01130(10) 0.7314(4) 0.0396(8) Uani 1 1 d . . . H15 H 1.0373 0.0027 0.6909 0.048 Uiso 1 1 calc R . . C16 C 1.2295(4) -0.00371(11) 0.6910(4) 0.0415(8) Uani 1 1 d . . . H16 H 1.2009 -0.0222 0.6224 0.050 Uiso 1 1 calc R . . C17 C 1.3689(4) 0.00892(11) 0.7530(4) 0.0432(8) Uani 1 1 d . . . C18 C 1.4120(4) 0.03533(11) 0.8543(4) 0.0437(8) Uani 1 1 d . . . H18 H 1.5080 0.0433 0.8971 0.052 Uiso 1 1 calc R . . C19 C 1.3153(4) 0.05012(11) 0.8932(4) 0.0402(8) Uani 1 1 d . . . H19 H 1.3447 0.0682 0.9632 0.048 Uiso 1 1 calc R . . C20 C 1.4332(5) -0.03045(13) 0.6161(5) 0.0519(10) Uani 1 1 d . . . H20A H 1.5149 -0.0362 0.5994 0.078 Uiso 1 1 calc R . . H20B H 1.3554 -0.0210 0.5337 0.078 Uiso 1 1 calc R . . H20C H 1.4028 -0.0534 0.6449 0.078 Uiso 1 1 calc R . . C21 C 1.1989(5) 0.07747(12) 1.4822(4) 0.0484(9) Uani 1 1 d . . . H21C H 1.2259 0.0707 1.5755 0.073 Uiso 1 1 calc R . . H21B H 1.1001 0.0859 1.4396 0.073 Uiso 1 1 calc R . . H21A H 1.2602 0.0979 1.4793 0.073 Uiso 1 1 calc R . . C22 C 0.5143(5) 0.13504(13) 0.3954(4) 0.0493(9) Uani 1 1 d . . . H22 H 0.5703 0.1270 0.3531 0.059 Uiso 1 1 calc R . . C23 C 0.3851(4) 0.15587(11) 0.3142(6) 0.0567(12) Uani 1 1 d . . . C24 C 0.3479(4) 0.15959(12) 0.1822(5) 0.0528(10) Uani 1 1 d . . . H24 H 0.4032 0.1478 0.1451 0.063 Uiso 1 1 calc R . . C25 C 0.2332(4) 0.17984(11) 0.1031(5) 0.0487(10) Uani 1 1 d . . . H25 H 0.2098 0.1824 0.0109 0.058 Uiso 1 1 calc R . . C26 C 0.1457(3) 0.19761(10) 0.1536(4) 0.0377(7) Uani 1 1 d . . . C27 C 0.1792(4) 0.19315(11) 0.2886(4) 0.0442(9) Uani 1 1 d . . . H27 H 0.1209 0.2039 0.3244 0.053 Uiso 1 1 calc R . . C28 C 0.2982(5) 0.17287(11) 0.3692(4) 0.0518(10) Uani 1 1 d . . . H28 H 0.3233 0.1700 0.4617 0.062 Uiso 1 1 calc R . . C29 C -0.0417(3) 0.24363(9) 0.1186(3) 0.0293(6) Uani 1 1 d . . . C30 C 0.0254(3) 0.27305(10) 0.2044(3) 0.0327(7) Uani 1 1 d . . . H30 H 0.1247 0.2762 0.2374 0.039 Uiso 1 1 calc R . . C31 C -0.0510(4) 0.29811(10) 0.2433(3) 0.0354(7) Uani 1 1 d . . . H31 H -0.0043 0.3181 0.3038 0.042 Uiso 1 1 calc R . . C32 C -0.1971(4) 0.29345(10) 0.1920(4) 0.0367(7) Uani 1 1 d . . . C33 C -0.2635(3) 0.26339(11) 0.1074(4) 0.0367(7) Uani 1 1 d . . . H33 H -0.3626 0.2599 0.0750 0.044 Uiso 1 1 calc R . . C34 C -0.1869(3) 0.23858(10) 0.0701(3) 0.0324(6) Uani 1 1 d . . . H34 H -0.2330 0.2182 0.0116 0.039 Uiso 1 1 calc R . . C35 C -0.0055(3) 0.22072(9) -0.0699(3) 0.0311(6) Uani 1 1 d . . . C36 C -0.0754(4) 0.19113(10) -0.1536(4) 0.0363(7) Uani 1 1 d . . . H36 H -0.0992 0.1693 -0.1186 0.044 Uiso 1 1 calc R . . C37 C -0.1109(4) 0.19336(11) -0.2890(4) 0.0401(8) Uani 1 1 d . . . H37 H -0.1584 0.1729 -0.3467 0.048 Uiso 1 1 calc R . . C38 C -0.0771(3) 0.22539(11) -0.3400(3) 0.0360(7) Uani 1 1 d . . . C39 C -0.0074(4) 0.25549(10) -0.2548(4) 0.0374(7) Uani 1 1 d . . . H39 H 0.0161 0.2775 -0.2892 0.045 Uiso 1 1 calc R . . C40 C 0.0268(4) 0.25301(10) -0.1207(4) 0.0352(7) Uani 1 1 d . . . H40 H 0.0727 0.2735 -0.0628 0.042 Uiso 1 1 calc R . . C41 C -0.2237(5) 0.34854(12) 0.3000(5) 0.0507(10) Uani 1 1 d . . . H41C H -0.2980 0.3631 0.3090 0.076 Uiso 1 1 calc R . . H41B H -0.1773 0.3644 0.2593 0.076 Uiso 1 1 calc R . . H41A H -0.1537 0.3402 0.3885 0.076 Uiso 1 1 calc R . . C42 C -0.1449(4) 0.19822(13) -0.5553(4) 0.0495(10) Uani 1 1 d . . . H42C H -0.1637 0.2056 -0.6463 0.074 Uiso 1 1 calc R . . H42B H -0.2302 0.1869 -0.5567 0.074 Uiso 1 1 calc R . . H42A H -0.0674 0.1798 -0.5210 0.074 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 Sb1 0.03495(13) 0.04044(14) 0.03788(13) -0.00124(10) 0.02006(10) 0.00282(10) F1 0.0520(15) 0.099(2) 0.0356(12) -0.0093(13) 0.0132(11) 0.0039(14) F2 0.0547(15) 0.0726(18) 0.0416(13) 0.0059(12) 0.0074(11) 0.0172(13) F3 0.0613(16) 0.0460(14) 0.096(2) -0.0187(13) 0.0495(16) 0.0018(12) F4 0.0562(15) 0.0580(15) 0.0804(18) -0.0055(13) 0.0481(14) -0.0053(12) F5 0.0557(13) 0.0374(11) 0.0553(13) 0.0041(10) 0.0350(11) 0.0085(10) F6 0.0585(15) 0.0451(13) 0.0839(18) 0.0040(12) 0.0517(14) 0.0012(11) O1 0.0540(16) 0.0455(15) 0.0294(12) 0.0047(11) 0.0138(12) 0.0023(12) O2 0.0400(15) 0.0586(18) 0.0670(19) -0.0202(15) 0.0267(14) -0.0024(13) O3 0.0386(14) 0.0466(15) 0.0669(18) -0.0178(13) 0.0287(14) -0.0003(12) O4 0.0351(13) 0.0537(16) 0.0330(12) -0.0060(11) 0.0155(10) -0.0029(11) N1 0.0333(14) 0.0333(14) 0.0293(13) 0.0022(11) 0.0138(11) 0.0040(11) N2 0.0273(13) 0.0366(14) 0.0321(13) -0.0023(11) 0.0119(11) 0.0037(11) C1 0.060(3) 0.055(2) 0.048(2) -0.0112(19) 0.027(2) -0.013(2) C2 0.039(2) 0.0318(17) 0.051(2) 0.0021(16) -0.0004(18) -0.0021(15) C3 0.074(3) 0.0315(18) 0.0261(16) 0.0036(14) 0.0014(18) -0.0099(18) C4 0.051(2) 0.0343(17) 0.0300(16) -0.0005(13) 0.0134(15) -0.0018(15) C5 0.0346(16) 0.0283(15) 0.0300(15) 0.0000(12) 0.0095(13) 0.0010(12) C6 0.0329(16) 0.0326(16) 0.0354(17) -0.0021(13) 0.0079(14) 0.0041(13) C7 0.0328(18) 0.0380(19) 0.048(2) -0.0022(16) 0.0030(16) 0.0037(15) C8 0.0251(14) 0.0351(16) 0.0277(14) 0.0023(12) 0.0081(12) 0.0020(12) C9 0.0301(15) 0.0310(15) 0.0329(16) 0.0041(12) 0.0098(13) 0.0024(12) C10 0.0323(16) 0.0346(16) 0.0319(16) -0.0023(13) 0.0101(13) -0.0007(13) C11 0.0287(15) 0.0444(19) 0.0274(15) 0.0016(13) 0.0089(13) -0.0017(13) C12 0.0381(18) 0.0345(17) 0.0317(16) 0.0069(13) 0.0083(14) 0.0015(14) C13 0.0311(16) 0.0327(16) 0.0342(16) 0.0006(13) 0.0103(13) 0.0041(13) C14 0.0390(18) 0.0340(16) 0.0345(16) 0.0047(13) 0.0187(14) 0.0073(14) C15 0.0391(18) 0.0363(18) 0.0438(19) -0.0031(15) 0.0187(16) -0.0045(14) C16 0.044(2) 0.0378(18) 0.0416(19) -0.0068(15) 0.0182(16) -0.0047(15) C17 0.0344(18) 0.0396(19) 0.054(2) -0.0030(16) 0.0181(17) 0.0021(15) C18 0.0334(18) 0.046(2) 0.048(2) -0.0062(17) 0.0151(16) -0.0024(15) C19 0.0352(17) 0.043(2) 0.0398(19) -0.0040(15) 0.0144(15) 0.0000(15) C20 0.046(2) 0.053(2) 0.059(2) -0.013(2) 0.025(2) 0.0033(18) C21 0.061(3) 0.051(2) 0.0333(18) 0.0006(16) 0.0211(18) 0.0014(19) C22 0.048(2) 0.051(2) 0.050(2) -0.0047(18) 0.0226(19) -0.0004(18) C23 0.0311(18) 0.0299(18) 0.097(4) -0.004(2) 0.017(2) 0.0018(14) C24 0.036(2) 0.045(2) 0.069(3) -0.006(2) 0.016(2) 0.0026(16) C25 0.0288(17) 0.0392(19) 0.072(3) -0.0083(18) 0.0164(18) -0.0007(14) C26 0.0254(15) 0.0315(16) 0.047(2) -0.0049(14) 0.0079(14) 0.0002(12) C27 0.0400(19) 0.0355(18) 0.0410(19) -0.0017(15) 0.0035(16) 0.0022(15) C28 0.049(2) 0.038(2) 0.044(2) 0.0006(16) -0.0022(18) -0.0042(17) C29 0.0258(14) 0.0333(16) 0.0286(15) 0.0017(12) 0.0119(12) 0.0047(12) C30 0.0249(14) 0.0375(17) 0.0306(15) -0.0022(13) 0.0078(12) 0.0002(12) C31 0.0318(16) 0.0383(18) 0.0350(17) -0.0073(13) 0.0139(14) -0.0031(13) C32 0.0339(17) 0.0378(18) 0.0428(18) -0.0029(14) 0.0210(15) 0.0019(14) C33 0.0245(15) 0.0417(18) 0.0424(18) -0.0023(15) 0.0135(14) -0.0005(13) C34 0.0284(15) 0.0350(16) 0.0315(15) -0.0018(13) 0.0114(13) -0.0015(12) C35 0.0278(15) 0.0332(16) 0.0343(16) -0.0023(12) 0.0157(13) 0.0040(12) C36 0.0346(17) 0.0365(17) 0.0430(18) -0.0067(14) 0.0220(15) -0.0060(14) C37 0.0370(18) 0.0420(19) 0.0446(19) -0.0156(15) 0.0211(16) -0.0087(15) C38 0.0251(15) 0.0465(19) 0.0379(17) -0.0043(15) 0.0153(13) 0.0016(13) C39 0.0382(18) 0.0365(18) 0.0408(18) -0.0010(14) 0.0206(15) 0.0009(14) C40 0.0338(16) 0.0330(16) 0.0384(18) -0.0069(13) 0.0157(14) -0.0028(13) C41 0.054(2) 0.047(2) 0.062(3) -0.0147(19) 0.035(2) -0.0005(18) C42 0.045(2) 0.066(3) 0.040(2) -0.0150(19) 0.0215(18) -0.0068(19) _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 Sb1 F6 1.856(2) . ? Sb1 F2 1.857(3) . ? Sb1 F1 1.863(3) . ? Sb1 F5 1.866(2) . ? Sb1 F3 1.869(2) . ? Sb1 F4 1.873(2) . ? O1 C11 1.372(4) . ? O1 C21 1.425(5) . ? O2 C17 1.370(5) . ? O2 C20 1.420(5) . ? O3 C32 1.364(4) . ? O3 C41 1.412(5) . ? O4 C38 1.366(4) . ? O4 C42 1.429(5) . ? N1 C5 1.377(4) . ? N1 C8 1.424(4) . ? N1 C14 1.427(4) . ? N2 C26 1.361(4) . ? N2 C29 1.434(4) . ? N2 C35 1.437(4) . ? C1 C22 1.316(6) . ? C1 C2 1.488(6) . ? C1 H1 0.9500 . ? C2 C7 1.382(6) . ? C2 C3 1.405(7) . ? C3 C4 1.389(6) . ? C3 H3 0.9500 . ? C4 C5 1.411(5) . ? C4 H4 0.9500 . ? C5 C6 1.416(5) . ? C6 C7 1.370(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.386(5) . ? C8 C13 1.397(5) . ? C9 C10 1.383(5) . ? C9 H9 0.9500 . ? C10 C11 1.387(5) . ? C10 H10 0.9500 . ? C11 C12 1.384(5) . ? C12 C13 1.372(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.376(5) . ? C14 C19 1.399(5) . ? C15 C16 1.394(5) . ? C15 H15 0.9500 . ? C16 C17 1.391(5) . ? C16 H16 0.9500 . ? C17 C18 1.380(5) . ? C18 C19 1.377(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21C 0.9800 . ? C21 H21B 0.9800 . ? C21 H21A 0.9800 . ? C22 C23 1.457(6) . ? C22 H22 0.9500 . ? C23 C24 1.352(7) . ? C23 C28 1.442(7) . ? C24 C25 1.344(6) . ? C24 H24 0.9500 . ? C25 C26 1.425(5) . ? C25 H25 0.9500 . ? C26 C27 1.395(6) . ? C27 C28 1.377(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.380(5) . ? C29 C34 1.390(4) . ? C30 C31 1.392(5) . ? C30 H30 0.9500 . ? C31 C32 1.394(5) . ? C31 H31 0.9500 . ? C32 C33 1.389(5) . ? C33 C34 1.378(5) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.379(5) . ? C35 C40 1.386(5) . ? C36 C37 1.389(5) . ? C36 H36 0.9500 . ? C37 C38 1.386(5) . ? C37 H37 0.9500 . ? C38 C39 1.401(5) . ? C39 C40 1.377(5) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 H41C 0.9800 . ? C41 H41B 0.9800 . ? C41 H41A 0.9800 . ? C42 H42C 0.9800 . ? C42 H42B 0.9800 . ? C42 H42A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F6 Sb1 F2 90.19(13) . . ? F6 Sb1 F1 90.45(13) . . ? F2 Sb1 F1 179.25(12) . . ? F6 Sb1 F5 90.80(10) . . ? F2 Sb1 F5 89.12(11) . . ? F1 Sb1 F5 91.26(12) . . ? F6 Sb1 F3 90.71(11) . . ? F2 Sb1 F3 89.64(13) . . ? F1 Sb1 F3 89.97(13) . . ? F5 Sb1 F3 178.04(11) . . ? F6 Sb1 F4 179.25(11) . . ? F2 Sb1 F4 89.60(13) . . ? F1 Sb1 F4 89.75(13) . . ? F5 Sb1 F4 89.91(10) . . ? F3 Sb1 F4 88.57(11) . . ? C11 O1 C21 116.9(3) . . ? C17 O2 C20 117.1(3) . . ? C32 O3 C41 117.8(3) . . ? C38 O4 C42 117.1(3) . . ? C5 N1 C8 121.2(3) . . ? C5 N1 C14 121.8(3) . . ? C8 N1 C14 117.1(3) . . ? C26 N2 C29 123.0(3) . . ? C26 N2 C35 120.5(3) . . ? C29 N2 C35 116.3(3) . . ? C22 C1 C2 123.4(4) . . ? C22 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C7 C2 C3 116.9(4) . . ? C7 C2 C1 115.7(4) . . ? C3 C2 C1 127.3(4) . . ? C4 C3 C2 122.6(4) . . ? C4 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C3 C4 C5 119.2(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 121.4(3) . . ? N1 C5 C6 120.5(3) . . ? C4 C5 C6 118.1(3) . . ? C7 C6 C5 120.7(4) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C2 122.4(4) . . ? C6 C7 H7 118.8 . . ? C2 C7 H7 118.8 . . ? C9 C8 C13 119.5(3) . . ? C9 C8 N1 120.9(3) . . ? C13 C8 N1 119.6(3) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.3(3) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? O1 C11 C12 115.7(3) . . ? O1 C11 C10 124.1(3) . . ? C12 C11 C10 120.2(3) . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 119.8(3) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? C15 C14 C19 119.9(3) . . ? C15 C14 N1 121.4(3) . . ? C19 C14 N1 118.7(3) . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 118.8(3) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? O2 C17 C18 115.1(3) . . ? O2 C17 C16 123.9(4) . . ? C18 C17 C16 121.0(4) . . ? C19 C18 C17 119.8(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C14 120.0(3) . . ? C18 C19 H19 120.0 . . ? C14 C19 H19 120.0 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 H21C 109.5 . . ? O1 C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? O1 C21 H21A 109.5 . . ? H21C C21 H21A 109.5 . . ? H21B C21 H21A 109.5 . . ? C1 C22 C23 125.4(5) . . ? C1 C22 H22 117.3 . . ? C23 C22 H22 117.3 . . ? C24 C23 C28 119.4(4) . . ? C24 C23 C22 117.7(4) . . ? C28 C23 C22 122.8(5) . . ? C25 C24 C23 120.5(4) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 121.9(5) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? N2 C26 C27 121.6(3) . . ? N2 C26 C25 119.7(4) . . ? C27 C26 C25 118.7(4) . . ? C28 C27 C26 118.9(4) . . ? C28 C27 H27 120.5 . . ? C26 C27 H27 120.5 . . ? C27 C28 C23 120.5(4) . . ? C27 C28 H28 119.8 . . ? C23 C28 H28 119.8 . . ? C30 C29 C34 120.2(3) . . ? C30 C29 N2 121.2(3) . . ? C34 C29 N2 118.4(3) . . ? C29 C30 C31 120.7(3) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C30 C31 C32 118.9(3) . . ? C30 C31 H31 120.5 . . ? C32 C31 H31 120.5 . . ? O3 C32 C33 115.2(3) . . ? O3 C32 C31 124.7(3) . . ? C33 C32 C31 120.0(3) . . ? C34 C33 C32 120.6(3) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C29 119.5(3) . . ? C33 C34 H34 120.3 . . ? C29 C34 H34 120.3 . . ? C36 C35 C40 120.4(3) . . ? C36 C35 N2 121.2(3) . . ? C40 C35 N2 118.4(3) . . ? C35 C36 C37 119.8(3) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C38 C37 C36 120.0(3) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? O4 C38 C37 125.3(3) . . ? O4 C38 C39 114.8(3) . . ? C37 C38 C39 119.9(3) . . ? C40 C39 C38 119.6(3) . . ? C40 C39 H39 120.2 . . ? C38 C39 H39 120.2 . . ? C39 C40 C35 120.3(3) . . ? C39 C40 H40 119.9 . . ? C35 C40 H40 119.9 . . ? O3 C41 H41C 109.5 . . ? O3 C41 H41B 109.5 . . ? H41C C41 H41B 109.5 . . ? O3 C41 H41A 109.5 . . ? H41C C41 H41A 109.5 . . ? H41B C41 H41A 109.5 . . ? O4 C42 H42C 109.5 . . ? O4 C42 H42B 109.5 . . ? H42C C42 H42B 109.5 . . ? O4 C42 H42A 109.5 . . ? H42C C42 H42A 109.5 . . ? H42B C42 H42A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 C1 C2 C7 -171.7(4) . . . . ? C22 C1 C2 C3 10.7(7) . . . . ? C7 C2 C3 C4 -1.8(6) . . . . ? C1 C2 C3 C4 175.9(4) . . . . ? C2 C3 C4 C5 0.8(6) . . . . ? C8 N1 C5 C4 162.3(3) . . . . ? C14 N1 C5 C4 -16.9(5) . . . . ? C8 N1 C5 C6 -17.4(5) . . . . ? C14 N1 C5 C6 163.4(3) . . . . ? C3 C4 C5 N1 -178.8(3) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? N1 C5 C6 C7 178.0(3) . . . . ? C4 C5 C6 C7 -1.8(5) . . . . ? C5 C6 C7 C2 0.8(6) . . . . ? C3 C2 C7 C6 0.9(6) . . . . ? C1 C2 C7 C6 -177.0(4) . . . . ? C5 N1 C8 C9 -45.3(5) . . . . ? C14 N1 C8 C9 133.9(3) . . . . ? C5 N1 C8 C13 135.0(3) . . . . ? C14 N1 C8 C13 -45.8(4) . . . . ? C13 C8 C9 C10 -2.1(5) . . . . ? N1 C8 C9 C10 178.2(3) . . . . ? C8 C9 C10 C11 0.4(5) . . . . ? C21 O1 C11 C12 178.7(3) . . . . ? C21 O1 C11 C10 -0.6(5) . . . . ? C9 C10 C11 O1 -179.2(3) . . . . ? C9 C10 C11 C12 1.5(5) . . . . ? O1 C11 C12 C13 179.0(3) . . . . ? C10 C11 C12 C13 -1.7(5) . . . . ? C11 C12 C13 C8 0.0(5) . . . . ? C9 C8 C13 C12 1.9(5) . . . . ? N1 C8 C13 C12 -178.4(3) . . . . ? C5 N1 C14 C15 -54.5(5) . . . . ? C8 N1 C14 C15 126.2(4) . . . . ? C5 N1 C14 C19 127.0(4) . . . . ? C8 N1 C14 C19 -52.2(4) . . . . ? C19 C14 C15 C16 -2.5(6) . . . . ? N1 C14 C15 C16 179.1(3) . . . . ? C14 C15 C16 C17 0.9(6) . . . . ? C20 O2 C17 C18 178.5(4) . . . . ? C20 O2 C17 C16 -3.2(6) . . . . ? C15 C16 C17 O2 -177.1(4) . . . . ? C15 C16 C17 C18 1.1(6) . . . . ? O2 C17 C18 C19 177.0(4) . . . . ? C16 C17 C18 C19 -1.4(6) . . . . ? C17 C18 C19 C14 -0.3(6) . . . . ? C15 C14 C19 C18 2.2(6) . . . . ? N1 C14 C19 C18 -179.3(3) . . . . ? C2 C1 C22 C23 -177.8(4) . . . . ? C1 C22 C23 C24 -174.7(4) . . . . ? C1 C22 C23 C28 6.3(7) . . . . ? C28 C23 C24 C25 1.9(6) . . . . ? C22 C23 C24 C25 -177.2(4) . . . . ? C23 C24 C25 C26 -0.9(6) . . . . ? C29 N2 C26 C27 11.0(5) . . . . ? C35 N2 C26 C27 -174.8(3) . . . . ? C29 N2 C26 C25 -167.5(3) . . . . ? C35 N2 C26 C25 6.8(5) . . . . ? C24 C25 C26 N2 177.3(4) . . . . ? C24 C25 C26 C27 -1.2(6) . . . . ? N2 C26 C27 C28 -176.3(3) . . . . ? C25 C26 C27 C28 2.2(5) . . . . ? C26 C27 C28 C23 -1.2(6) . . . . ? C24 C23 C28 C27 -0.8(6) . . . . ? C22 C23 C28 C27 178.2(4) . . . . ? C26 N2 C29 C30 60.6(5) . . . . ? C35 N2 C29 C30 -113.8(3) . . . . ? C26 N2 C29 C34 -123.2(4) . . . . ? C35 N2 C29 C34 62.4(4) . . . . ? C34 C29 C30 C31 -0.2(5) . . . . ? N2 C29 C30 C31 175.9(3) . . . . ? C29 C30 C31 C32 -1.2(5) . . . . ? C41 O3 C32 C33 -178.0(4) . . . . ? C41 O3 C32 C31 1.7(6) . . . . ? C30 C31 C32 O3 -177.4(3) . . . . ? C30 C31 C32 C33 2.3(5) . . . . ? O3 C32 C33 C34 177.8(3) . . . . ? C31 C32 C33 C34 -1.9(6) . . . . ? C32 C33 C34 C29 0.5(5) . . . . ? C30 C29 C34 C33 0.6(5) . . . . ? N2 C29 C34 C33 -175.6(3) . . . . ? C26 N2 C35 C36 75.2(4) . . . . ? C29 N2 C35 C36 -110.2(4) . . . . ? C26 N2 C35 C40 -105.5(4) . . . . ? C29 N2 C35 C40 69.1(4) . . . . ? C40 C35 C36 C37 1.4(5) . . . . ? N2 C35 C36 C37 -179.3(3) . . . . ? C35 C36 C37 C38 -0.5(5) . . . . ? C42 O4 C38 C37 -14.5(5) . . . . ? C42 O4 C38 C39 165.4(3) . . . . ? C36 C37 C38 O4 179.7(3) . . . . ? C36 C37 C38 C39 -0.2(5) . . . . ? O4 C38 C39 C40 -179.9(3) . . . . ? C37 C38 C39 C40 0.0(5) . . . . ? C38 C39 C40 C35 1.0(5) . . . . ? C36 C35 C40 C39 -1.6(5) . . . . ? N2 C35 C40 C39 179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.19 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.403 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.122 #===END