# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Scott D. Bunge' _publ_contact_author_address ;Department of Chemistry Kent State University Kent, OH 44242 ; _publ_contact_author_email sbunge@kent.edu _publ_contact_author_phone '(+1) 330 672-9445' _publ_contact_author_fax '(+1) 330 672-3816' loop_ _publ_author_name _publ_author_address S.D.Bunge ;Department of Chemistry and Biochemistry Kent State University Kent, OH 44242 ; Yu.A.Getmanenko ;School of Chemistry and Biochemistry Georgia Institute of Technology Atlanta, GA 30332-0400, USA ; J.M.Hales ;The College of Optics and Photonics and Department of Physics University of Central Florida Orlando, FL 32816-2700 ; M.Balu ;The College of Optics and Photonics and Department of Physics University of Central Florida Orlando, FL 32816-2700 ; J.Fu ;The College of Optics and Photonics and Department of Physics University of Central Florida Orlando, FL 32816-2700 ; E.Zojer ;School of Chemistry and Biochemistry Georgia Institute of Technology Atlanta, GA 30332-0400, USA ; ; O.Kwon ; ;School of Chemistry and Biochemistry Georgia Institute of Technology Atlanta, GA 30332-0400, USA ; J.Mendez ;Beckman Institute California Institute of Technology Pasadena, CA 91125, USA ; S.Thayumanavan ;Beckman Institute California Institute of Technology Pasadena, CA 91125, USA ; G.Walker ;Department of Chemistry University of Arizona Tucson, AZ 85721, USA ; Q.Zhang ;School of Chemistry and Biochemistry Georgia Institute of Technology Atlanta, GA 30332-0400, USA ; J.-L.Bredas ;School of Chemistry and Biochemistry Georgia Institute of Technology Atlanta, GA 30332-0400, USA ; D.J.Hagan ;The College of Optics and Photonics and Department of Physics University of Central Florida Orlando, FL 32816-2700 ; ; E.W.van Stryland ; ;The College of Optics and Photonics and Department of Physics University of Central Florida Orlando, FL 32816-2700 ; S.Barlow ;School of Chemistry and Biochemistry Georgia Institute of Technology Atlanta, GA 30332-0400, USA ; S.R.Marder ;School of Chemistry and Biochemistry Georgia Institute of Technology Atlanta, GA 30332-0400, USA ; _publ_section_title ; Characterisation of a Dipolar Chromophore with Third-Harmonic Generation Applications in the Near-IR ; # Attachment '- Getmanenko&al.cif.txt' data_good _database_code_depnum_ccdc_archive 'CCDC 851132' #TrackingRef '- Getmanenko&al.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; E-2-tricyanovinyl-3-n-hexyl-5- [4-{bis(4-n-butylphenyl)amino}-2-methoxystyryl]-thiophene ; _chemical_name_common ; E-2-tricyanovinyl-3-n-hexyl-5-(4-(bis(4-n-butylphenyl)amino)- 2-methoxystyryl)-thiophene ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H48 N4 O S' _chemical_formula_weight 680.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 10.9857(8) _cell_length_b 15.0354(8) _cell_length_c 46.669(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.149(2) _cell_angle_gamma 90.00 _cell_volume 7708.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6349 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.05 _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2912 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9677 _exptl_absorpt_correction_T_max 0.9759 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '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 30633 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -55 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_theta_min 0.87 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6815 _reflns_number_gt 5410 _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.1899P] 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 6815 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1430 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.19023(4) 0.40110(3) 0.232985(9) 0.02547(15) Uani 1 1 d . . . O1 O 0.10468(13) 0.28604(8) 0.34456(3) 0.0314(3) Uani 1 1 d . . . N1 N 0.31286(16) 0.49379(12) 0.11650(4) 0.0366(4) Uani 1 1 d . . . N2 N 0.27899(18) 0.58665(11) 0.20192(4) 0.0410(5) Uani 1 1 d . . . N3 N 0.22520(16) 0.26179(11) 0.13133(4) 0.0366(4) Uani 1 1 d . . . N4 N -0.01636(15) 0.52106(10) 0.40916(3) 0.0273(4) Uani 1 1 d . . . C1 C 0.28605(17) 0.47440(12) 0.13940(4) 0.0265(4) Uani 1 1 d . . . C2 C 0.25558(16) 0.45204(12) 0.16824(4) 0.0244(4) Uani 1 1 d . . . C3 C 0.26597(17) 0.52478(13) 0.18774(4) 0.0276(4) Uani 1 1 d . . . C4 C 0.22354(15) 0.36565(12) 0.17567(4) 0.0219(4) Uani 1 1 d . . . C5 C 0.22331(16) 0.30562(12) 0.15143(4) 0.0249(4) Uani 1 1 d . . . C6 C 0.19408(15) 0.33120(12) 0.20317(4) 0.0217(4) Uani 1 1 d . . . C7 C 0.16905(15) 0.24235(12) 0.21113(4) 0.0227(4) Uani 1 1 d . . . C8 C 0.15626(18) 0.16363(12) 0.19111(4) 0.0275(4) Uani 1 1 d . . . H8A H 0.2356 0.1528 0.1817 0.033 Uiso 1 1 calc R . . H8B H 0.0966 0.1788 0.1759 0.033 Uiso 1 1 calc R . . C9 C 0.11554(18) 0.07848(12) 0.20580(4) 0.0284(4) Uani 1 1 d . . . H9A H 0.0377 0.0896 0.2158 0.034 Uiso 1 1 calc R . . H9B H 0.1769 0.0616 0.2204 0.034 Uiso 1 1 calc R . . C10 C 0.09864(18) 0.00166(12) 0.18498(4) 0.0297(4) Uani 1 1 d . . . H10A H 0.1759 -0.0086 0.1746 0.036 Uiso 1 1 calc R . . H10B H 0.0358 0.0179 0.1707 0.036 Uiso 1 1 calc R . . C11 C 0.06084(18) -0.08397(12) 0.19990(5) 0.0317(5) Uani 1 1 d . . . H11A H 0.1171 -0.0950 0.2161 0.038 Uiso 1 1 calc R . . H11B H -0.0218 -0.0759 0.2079 0.038 Uiso 1 1 calc R . . C12 C 0.0603(2) -0.16517(13) 0.18057(5) 0.0434(6) Uani 1 1 d . . . H12A H 0.0003 -0.1561 0.1650 0.052 Uiso 1 1 calc R . . H12B H 0.1416 -0.1719 0.1717 0.052 Uiso 1 1 calc R . . C13 C 0.0288(3) -0.24961(15) 0.19666(7) 0.0650(8) Uani 1 1 d . . . H13A H 0.0885 -0.2593 0.2120 0.097 Uiso 1 1 calc R . . H13B H 0.0303 -0.3002 0.1834 0.097 Uiso 1 1 calc R . . H13C H -0.0526 -0.2440 0.2050 0.097 Uiso 1 1 calc R . . C14 C 0.15223(16) 0.23494(12) 0.24046(4) 0.0246(4) Uani 1 1 d . . . H14 H 0.1389 0.1793 0.2496 0.030 Uiso 1 1 calc R . . C15 C 0.15618(15) 0.31411(12) 0.25557(4) 0.0240(4) Uani 1 1 d . . . C16 C 0.13107(16) 0.32551(12) 0.28539(4) 0.0240(4) Uani 1 1 d . . . H16 H 0.1319 0.2745 0.2974 0.029 Uiso 1 1 calc R . . C17 C 0.10607(16) 0.40568(12) 0.29731(4) 0.0239(4) Uani 1 1 d . . . H17 H 0.1097 0.4544 0.2844 0.029 Uiso 1 1 calc R . . C18 C 0.07496(16) 0.42958(12) 0.32627(4) 0.0226(4) Uani 1 1 d . . . C19 C 0.04074(16) 0.51811(12) 0.33163(4) 0.0250(4) Uani 1 1 d . . . H19 H 0.0398 0.5587 0.3160 0.030 Uiso 1 1 calc R . . C20 C 0.00861(17) 0.54894(12) 0.35823(4) 0.0265(4) Uani 1 1 d . . . H20 H -0.0159 0.6091 0.3606 0.032 Uiso 1 1 calc R . . C21 C 0.01202(16) 0.49145(12) 0.38188(4) 0.0237(4) Uani 1 1 d . . . C22 C 0.04521(17) 0.40222(12) 0.37726(4) 0.0245(4) Uani 1 1 d . . . H22 H 0.0474 0.3621 0.3930 0.029 Uiso 1 1 calc R . . C23 C 0.07451(16) 0.37237(12) 0.35026(4) 0.0236(4) Uani 1 1 d . . . C24 C 0.1127(3) 0.22492(14) 0.36791(5) 0.0462(6) Uani 1 1 d . . . H24A H 0.1761 0.2446 0.3813 0.069 Uiso 1 1 calc R . . H24B H 0.1331 0.1657 0.3606 0.069 Uiso 1 1 calc R . . H24C H 0.0343 0.2225 0.3779 0.069 Uiso 1 1 calc R . . C25 C -0.03846(17) 0.61383(12) 0.41482(4) 0.0257(4) Uani 1 1 d . . . C26 C -0.15068(18) 0.64000(14) 0.42533(4) 0.0310(5) Uani 1 1 d . . . H26 H -0.2117 0.5969 0.4292 0.037 Uiso 1 1 calc R . . C27 C -0.17329(18) 0.72951(14) 0.43016(4) 0.0324(5) Uani 1 1 d . . . H27 H -0.2501 0.7470 0.4376 0.039 Uiso 1 1 calc R . . C28 C -0.08679(18) 0.79411(13) 0.42443(4) 0.0300(4) Uani 1 1 d . . . C29 C 0.02628(18) 0.76596(13) 0.41442(4) 0.0314(5) Uani 1 1 d . . . H29 H 0.0879 0.8088 0.4108 0.038 Uiso 1 1 calc R . . C30 C 0.05046(17) 0.67677(12) 0.40967(4) 0.0286(4) Uani 1 1 d . . . H30 H 0.1281 0.6589 0.4029 0.034 Uiso 1 1 calc R . . C31 C -0.1149(2) 0.89178(14) 0.42751(4) 0.0403(5) Uani 1 1 d . . . H31A H -0.0497 0.9204 0.4389 0.048 Uiso 1 1 calc R . . H31B H -0.1923 0.8987 0.4381 0.048 Uiso 1 1 calc R . . C32 C -0.12564(19) 0.93867(14) 0.39876(4) 0.0348(5) Uani 1 1 d . . . H32A H -0.0450 0.9382 0.3894 0.042 Uiso 1 1 calc R . . H32B H -0.1825 0.9047 0.3864 0.042 Uiso 1 1 calc R . . C33 C -0.1700(2) 1.03409(14) 0.40071(5) 0.0424(5) Uani 1 1 d . . . H33A H -0.1716 1.0597 0.3812 0.051 Uiso 1 1 calc R . . H33B H -0.2546 1.0337 0.4079 0.051 Uiso 1 1 calc R . . C34 C -0.0952(3) 1.09353(15) 0.41955(6) 0.0558(7) Uani 1 1 d . . . H34A H -0.1031 1.0744 0.4395 0.084 Uiso 1 1 calc R . . H34B H -0.1239 1.1550 0.4176 0.084 Uiso 1 1 calc R . . H34C H -0.0096 1.0901 0.4138 0.084 Uiso 1 1 calc R . . C35 C -0.02937(18) 0.46078(12) 0.43296(4) 0.0275(4) Uani 1 1 d . . . C36 C 0.0488(2) 0.46766(14) 0.45597(4) 0.0370(5) Uani 1 1 d . . . H36 H 0.1120 0.5108 0.4558 0.044 Uiso 1 1 calc R . . C37 C 0.0353(2) 0.41171(15) 0.47942(4) 0.0409(5) Uani 1 1 d . . . H37 H 0.0895 0.4174 0.4952 0.049 Uiso 1 1 calc R . . C38 C -0.0554(2) 0.34774(14) 0.48029(4) 0.0358(5) Uani 1 1 d . . . C39 C -0.1332(2) 0.34155(14) 0.45682(4) 0.0388(5) Uani 1 1 d . . . H39 H -0.1963 0.2983 0.4569 0.047 Uiso 1 1 calc R . . C40 C -0.12085(19) 0.39687(14) 0.43337(4) 0.0350(5) Uani 1 1 d . . . H40 H -0.1748 0.3913 0.4175 0.042 Uiso 1 1 calc R . . C41 C -0.0708(2) 0.28803(15) 0.50614(5) 0.0433(5) Uani 1 1 d . . . H41A H -0.1564 0.2913 0.5126 0.052 Uiso 1 1 calc R . . H41B H -0.0187 0.3106 0.5219 0.052 Uiso 1 1 calc R . . C42 C -0.0383(2) 0.19065(15) 0.50041(5) 0.0401(5) Uani 1 1 d . . . H42A H -0.0555 0.1554 0.5179 0.048 Uiso 1 1 calc R . . H42B H -0.0912 0.1678 0.4849 0.048 Uiso 1 1 calc R . . C43 C 0.0934(2) 0.17653(18) 0.49203(5) 0.0524(6) Uani 1 1 d . . . H43A H 0.1463 0.2018 0.5072 0.063 Uiso 1 1 calc R . . H43B H 0.1096 0.2097 0.4741 0.063 Uiso 1 1 calc R . . C44 C 0.1278(2) 0.07940(19) 0.48752(6) 0.0588(7) Uani 1 1 d . . . H44A H 0.1158 0.0464 0.5054 0.088 Uiso 1 1 calc R . . H44B H 0.2134 0.0755 0.4818 0.088 Uiso 1 1 calc R . . H44C H 0.0764 0.0538 0.4724 0.088 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 S1 0.0327(3) 0.0218(3) 0.0220(3) -0.00274(18) 0.00201(19) -0.00285(19) O1 0.0506(9) 0.0178(7) 0.0257(7) 0.0013(5) -0.0005(6) 0.0050(6) N1 0.0384(10) 0.0382(10) 0.0333(10) 0.0034(8) 0.0017(8) -0.0047(8) N2 0.0536(12) 0.0272(10) 0.0421(11) -0.0047(8) -0.0015(9) -0.0056(8) N3 0.0487(11) 0.0307(10) 0.0305(10) -0.0038(8) 0.0056(8) -0.0016(8) N4 0.0404(9) 0.0221(8) 0.0195(8) 0.0010(6) 0.0063(7) -0.0017(7) C1 0.0263(10) 0.0246(10) 0.0285(11) 0.0001(8) -0.0001(8) -0.0024(8) C2 0.0241(9) 0.0232(10) 0.0259(10) -0.0014(8) -0.0004(7) 0.0008(7) C3 0.0313(10) 0.0224(10) 0.0291(10) 0.0025(9) 0.0018(8) -0.0008(8) C4 0.0188(9) 0.0257(10) 0.0210(9) -0.0027(7) -0.0012(7) 0.0019(7) C5 0.0267(10) 0.0235(10) 0.0246(10) 0.0010(8) 0.0039(7) -0.0017(8) C6 0.0207(9) 0.0206(9) 0.0238(10) -0.0050(7) -0.0002(7) 0.0015(7) C7 0.0210(9) 0.0228(9) 0.0245(9) -0.0005(7) -0.0003(7) 0.0024(7) C8 0.0339(10) 0.0237(10) 0.0250(10) -0.0031(8) 0.0022(8) 0.0009(8) C9 0.0321(10) 0.0236(10) 0.0294(10) 0.0001(8) 0.0004(8) -0.0004(8) C10 0.0304(10) 0.0237(10) 0.0350(11) -0.0043(8) -0.0010(8) -0.0002(8) C11 0.0290(10) 0.0240(10) 0.0420(12) -0.0021(9) -0.0041(9) 0.0005(8) C12 0.0382(12) 0.0270(11) 0.0649(16) -0.0127(11) -0.0050(11) -0.0020(9) C13 0.0606(17) 0.0249(12) 0.109(2) -0.0064(14) -0.0020(16) -0.0073(12) C14 0.0271(10) 0.0225(10) 0.0243(10) -0.0002(8) 0.0013(7) 0.0005(8) C15 0.0207(9) 0.0244(10) 0.0269(10) 0.0008(8) -0.0012(7) 0.0005(7) C16 0.0263(10) 0.0251(10) 0.0205(9) 0.0015(7) -0.0013(7) 0.0006(8) C17 0.0230(9) 0.0246(10) 0.0242(10) 0.0026(8) -0.0010(7) -0.0018(7) C18 0.0225(9) 0.0228(9) 0.0225(9) -0.0009(7) -0.0001(7) -0.0013(7) C19 0.0297(10) 0.0226(10) 0.0228(10) 0.0036(7) 0.0016(7) -0.0001(8) C20 0.0343(10) 0.0197(9) 0.0254(10) 0.0015(8) 0.0021(8) 0.0020(8) C21 0.0262(10) 0.0225(9) 0.0225(9) -0.0009(7) 0.0016(7) -0.0021(8) C22 0.0312(10) 0.0206(9) 0.0216(9) 0.0050(7) -0.0003(8) -0.0037(8) C23 0.0248(9) 0.0189(9) 0.0271(10) -0.0007(7) -0.0005(7) 0.0005(7) C24 0.0840(18) 0.0244(11) 0.0301(11) 0.0046(9) -0.0031(11) 0.0113(11) C25 0.0352(11) 0.0240(10) 0.0181(9) -0.0007(7) 0.0012(8) 0.0001(8) C26 0.0322(11) 0.0368(12) 0.0239(10) -0.0002(8) 0.0037(8) -0.0022(9) C27 0.0338(11) 0.0395(12) 0.0241(10) -0.0017(9) 0.0041(8) 0.0106(9) C28 0.0411(11) 0.0296(11) 0.0193(9) -0.0001(8) 0.0012(8) 0.0098(9) C29 0.0372(11) 0.0264(11) 0.0306(11) 0.0024(8) 0.0016(8) 0.0010(8) C30 0.0305(10) 0.0260(10) 0.0295(10) 0.0000(8) 0.0047(8) 0.0040(8) C31 0.0582(14) 0.0307(12) 0.0319(12) -0.0004(9) 0.0068(10) 0.0154(10) C32 0.0389(12) 0.0316(11) 0.0339(11) -0.0005(9) -0.0017(9) 0.0061(9) C33 0.0535(14) 0.0336(12) 0.0402(13) 0.0048(10) -0.0022(10) 0.0142(10) C34 0.0771(19) 0.0303(13) 0.0599(17) 0.0024(11) -0.0093(14) 0.0081(12) C35 0.0385(11) 0.0238(10) 0.0203(9) 0.0005(8) 0.0049(8) -0.0010(8) C36 0.0455(13) 0.0359(12) 0.0296(11) 0.0019(9) -0.0013(9) -0.0125(10) C37 0.0526(14) 0.0458(13) 0.0244(11) 0.0046(9) -0.0080(9) -0.0110(11) C38 0.0468(12) 0.0356(12) 0.0250(11) 0.0058(9) 0.0028(9) -0.0031(10) C39 0.0438(12) 0.0393(12) 0.0334(12) 0.0072(10) -0.0007(9) -0.0146(10) C40 0.0437(12) 0.0375(12) 0.0238(10) 0.0064(9) -0.0022(9) -0.0092(10) C41 0.0554(14) 0.0466(14) 0.0281(11) 0.0095(10) 0.0025(10) -0.0086(11) C42 0.0460(13) 0.0437(13) 0.0306(11) 0.0132(10) 0.0004(9) -0.0055(10) C43 0.0468(14) 0.0651(17) 0.0453(14) 0.0132(12) 0.0026(11) -0.0077(12) C44 0.0501(15) 0.080(2) 0.0464(15) 0.0091(14) 0.0007(11) 0.0099(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C15 1.7215(18) . ? S1 C6 1.7443(17) . ? O1 C23 1.366(2) . ? O1 C24 1.428(2) . ? N1 C1 1.147(2) . ? N2 C3 1.150(2) . ? N3 C5 1.147(2) . ? N4 C21 1.385(2) . ? N4 C25 1.440(2) . ? N4 C35 1.441(2) . ? C1 C2 1.428(3) . ? C2 C4 1.390(3) . ? C2 C3 1.427(3) . ? C4 C6 1.422(2) . ? C4 C5 1.447(2) . ? C6 C7 1.414(2) . ? C7 C14 1.386(3) . ? C7 C8 1.514(2) . ? C8 C9 1.520(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.521(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.522(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.515(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.430(2) . ? C16 C17 1.356(3) . ? C16 H16 0.9500 . ? C17 C18 1.440(3) . ? C17 H17 0.9500 . ? C18 C19 1.406(3) . ? C18 C23 1.412(3) . ? C19 C20 1.372(3) . ? C19 H19 0.9500 . ? C20 C21 1.402(2) . ? C20 H20 0.9500 . ? C21 C22 1.407(2) . ? C22 C23 1.377(3) . ? C22 H22 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C30 1.382(3) . ? C25 C26 1.385(3) . ? C26 C27 1.387(3) . ? C26 H26 0.9500 . ? C27 C28 1.385(3) . ? C27 H27 0.9500 . ? C28 C29 1.394(3) . ? C28 C31 1.508(3) . ? C29 C30 1.385(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.520(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.518(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.498(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.377(3) . ? C35 C40 1.391(3) . ? C36 C37 1.388(3) . ? C36 H36 0.9500 . ? C37 C38 1.386(3) . ? C37 H37 0.9500 . ? C38 C39 1.391(3) . ? C38 C41 1.513(3) . ? C39 C40 1.381(3) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C42 1.531(3) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.515(3) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.523(4) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 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 C15 S1 C6 92.09(9) . . ? C23 O1 C24 118.51(15) . . ? C21 N4 C25 121.22(15) . . ? C21 N4 C35 121.96(15) . . ? C25 N4 C35 116.79(14) . . ? N1 C1 C2 178.2(2) . . ? C4 C2 C3 125.25(17) . . ? C4 C2 C1 121.01(16) . . ? C3 C2 C1 113.71(16) . . ? N2 C3 C2 175.0(2) . . ? C2 C4 C6 128.59(16) . . ? C2 C4 C5 112.83(16) . . ? C6 C4 C5 118.58(16) . . ? N3 C5 C4 176.32(19) . . ? C7 C6 C4 128.76(16) . . ? C7 C6 S1 110.77(13) . . ? C4 C6 S1 120.44(13) . . ? C14 C7 C6 111.21(16) . . ? C14 C7 C8 122.28(16) . . ? C6 C7 C8 126.47(16) . . ? C7 C8 C9 114.03(15) . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 112.78(15) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 112.53(16) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 114.15(18) . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 112.3(2) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C7 115.46(17) . . ? C15 C14 H14 122.3 . . ? C7 C14 H14 122.3 . . ? C14 C15 C16 126.38(17) . . ? C14 C15 S1 110.37(14) . . ? C16 C15 S1 123.20(14) . . ? C17 C16 C15 123.08(17) . . ? C17 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? C16 C17 C18 130.96(17) . . ? C16 C17 H17 114.5 . . ? C18 C17 H17 114.5 . . ? C19 C18 C23 115.74(16) . . ? C19 C18 C17 117.87(16) . . ? C23 C18 C17 126.39(16) . . ? C20 C19 C18 123.39(17) . . ? C20 C19 H19 118.3 . . ? C18 C19 H19 118.3 . . ? C19 C20 C21 119.84(17) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? N4 C21 C20 121.32(16) . . ? N4 C21 C22 120.43(16) . . ? C20 C21 C22 118.25(16) . . ? C23 C22 C21 120.83(17) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? O1 C23 C22 123.05(16) . . ? O1 C23 C18 115.03(15) . . ? C22 C23 C18 121.91(16) . . ? O1 C24 H24A 109.5 . . ? O1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C30 C25 C26 119.83(17) . . ? C30 C25 N4 120.78(17) . . ? C26 C25 N4 119.38(17) . . ? C25 C26 C27 119.54(18) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 121.72(18) . . ? C28 C27 H27 119.1 . . ? C26 C27 H27 119.1 . . ? C27 C28 C29 117.64(18) . . ? C27 C28 C31 121.57(18) . . ? C29 C28 C31 120.72(19) . . ? C30 C29 C28 121.27(19) . . ? C30 C29 H29 119.4 . . ? C28 C29 H29 119.4 . . ? C25 C30 C29 119.96(18) . . ? C25 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C28 C31 C32 112.52(17) . . ? C28 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? C28 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? C33 C32 C31 114.16(17) . . ? C33 C32 H32A 108.7 . . ? C31 C32 H32A 108.7 . . ? C33 C32 H32B 108.7 . . ? C31 C32 H32B 108.7 . . ? H32A C32 H32B 107.6 . . ? C34 C33 C32 115.07(19) . . ? C34 C33 H33A 108.5 . . ? C32 C33 H33A 108.5 . . ? C34 C33 H33B 108.5 . . ? C32 C33 H33B 108.5 . . ? H33A C33 H33B 107.5 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 C35 C40 119.36(18) . . ? C36 C35 N4 119.40(17) . . ? C40 C35 N4 121.23(17) . . ? C35 C36 C37 120.10(19) . . ? C35 C36 H36 120.0 . . ? C37 C36 H36 120.0 . . ? C38 C37 C36 121.46(19) . . ? C38 C37 H37 119.3 . . ? C36 C37 H37 119.3 . . ? C37 C38 C39 117.65(18) . . ? C37 C38 C41 121.13(19) . . ? C39 C38 C41 121.21(19) . . ? C40 C39 C38 121.46(19) . . ? C40 C39 H39 119.3 . . ? C38 C39 H39 119.3 . . ? C39 C40 C35 119.97(19) . . ? C39 C40 H40 120.0 . . ? C35 C40 H40 120.0 . . ? C38 C41 C42 113.67(18) . . ? C38 C41 H41A 108.8 . . ? C42 C41 H41A 108.8 . . ? C38 C41 H41B 108.8 . . ? C42 C41 H41B 108.8 . . ? H41A C41 H41B 107.7 . . ? C43 C42 C41 113.75(19) . . ? C43 C42 H42A 108.8 . . ? C41 C42 H42A 108.8 . . ? C43 C42 H42B 108.8 . . ? C41 C42 H42B 108.8 . . ? H42A C42 H42B 107.7 . . ? C42 C43 C44 114.0(2) . . ? C42 C43 H43A 108.7 . . ? C44 C43 H43A 108.7 . . ? C42 C43 H43B 108.7 . . ? C44 C43 H43B 108.7 . . ? H43A C43 H43B 107.6 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.242 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.061