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 'Samson Jenekhe' 'Amit Babel' 'Jessica M. Hancock' 'Christopher J. Tonzola' _publ_contact_author_name 'Samson Jenekhe' _publ_contact_author_address ; Department of Chemical Engineering University of Washington Box 351750 Benson Hall, Room 105 Seattle Washington 98195-1750 UNITED STATES OF AMERICA ; _publ_contact_author_email JENEKHE@U.WASHINGTON.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Quinoidal Oligoquinoline: A Novel Quinodimethane Exhibiting High Electroluminescence Efficiency and p-Channel Field Effect Charge Transport ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map and were refined with a riding model. H atoms were placed in geometrically idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A. U~iso~ values were fixed such that they were 1.2U~eq~ of their parent atom U~eq~ for CH's and 1.5U~eq~ of their parent atom U~eq~ in case of methyl groups. ; _publ_section_references ; Altomare, A.; Cascarano, G.; Giacovazzo, C.; Burla, M.C.; Polidori, G.; Camalli, M. (1994) J. Appl. Cryst. 27, 435-442. MacKay, S.; Gilmore, C.J.; Edwards, C.; Tremayne, M.; Stewart, N.; Shankland, K. (1998) "maXus: a computer program for the solution and refinement of crystal structures from diffraction data" University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan. Otinowski, Z.; Minor, W. (1996) Methods in Enzymology, 276, 307-326. Sheldrick, G. M. (1997) SHELXL97 University of G\"ottingen, Germany. ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 282777' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'BDBPQ' ; _chemical_name_common BDBPQ _chemical_melting_point ? _chemical_formula_moiety 'C56 H40 N2, 2(C H Cl3)' _chemical_formula_sum 'C58 H42 Cl6 N2' _chemical_formula_weight 979.64 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P c' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P -2yc' _symmetry_Int_Tables_number 7 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 17.7390(7) _cell_length_b 5.9890(2) _cell_length_c 25.1160(10) _cell_angle_alpha 90.00 _cell_angle_beta 120.6771(16) _cell_angle_gamma 90.00 _cell_volume 2294.88(15) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 536 _exptl_crystal_description neddle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 0.418 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7904 _exptl_absorpt_correction_T_max 0.9633 _exptl_absorpt_process_details Denzo2000 _exptl_special_details ; Data was collected with \w and \f scans in 1.4^o^ increments with 40 second exposures per degree. Crystal-to-detector distance was 30 mm. 44843 full and partial reflection were integrated. ; _diffrn_ambient_temperature 130(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 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 7818 _diffrn_reflns_av_R_equivalents 0.0894 _diffrn_reflns_av_sigmaI/netI 0.1650 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.68 _reflns_number_total 7818 _reflns_number_gt 3951 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus, Zortep' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. 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^)+(0.0650P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack (1983), 3454 Friedel pairs' _refine_ls_abs_structure_Flack 0.4(1) _refine_ls_number_reflns 7818 _refine_ls_number_parameters 596 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1616 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1680 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 -0.1647(2) 0.3552(4) 0.44968(12) 0.0796(7) Uani 1 1 d . . . Cl2 Cl -0.25920(15) -0.0553(4) 0.41772(10) 0.0714(7) Uani 1 1 d . . . Cl3 Cl -0.07151(15) -0.0645(4) 0.48113(10) 0.0707(7) Uani 1 1 d . . . Cl4 Cl 0.06826(15) 0.3308(4) 0.45483(10) 0.0673(6) Uani 1 1 d . . . Cl5 Cl 0.25337(16) 0.3695(5) 0.50517(10) 0.0881(9) Uani 1 1 d . . . Cl6 Cl 0.14098(18) 0.7472(3) 0.44606(11) 0.0714(7) Uani 1 1 d . . . N1 N -0.2963(4) 0.8822(9) 0.5606(2) 0.0264(13) Uani 1 1 d . . . N2 N -0.6972(3) -0.4026(8) 0.3599(2) 0.0214(13) Uani 1 1 d . . . C1 C -0.2433(4) 1.2048(10) 0.6292(3) 0.0256(17) Uani 1 1 d . . . H1 H -0.2763 1.3382 0.6042 0.031 Uiso 1 1 calc R . . C2 C -0.3049(5) 1.0063(10) 0.6006(3) 0.0258(17) Uani 1 1 d . . . C3 C -0.3715(4) 0.9703(10) 0.6146(3) 0.0231(16) Uani 1 1 d . . . H3 H -0.3758 1.0674 0.6429 0.028 Uiso 1 1 calc R . . C4 C -0.4305(4) 0.7972(10) 0.5883(3) 0.0232(16) Uani 1 1 d . . . C5 C -0.4217(4) 0.6551(10) 0.5455(3) 0.0235(16) Uani 1 1 d . . . C6 C -0.3548(4) 0.7058(10) 0.5331(3) 0.0218(16) Uani 1 1 d . . . C7 C -0.3442(5) 0.5690(10) 0.4925(3) 0.0277(17) Uani 1 1 d . . . H7 H -0.2997 0.6022 0.4833 0.033 Uiso 1 1 calc R . . C8 C -0.3972(4) 0.3871(10) 0.4659(3) 0.0240(16) Uani 1 1 d . . . H8 H -0.3860 0.2906 0.4406 0.029 Uiso 1 1 calc R . . C9 C -0.4679(4) 0.3386(11) 0.4747(3) 0.0241(16) Uani 1 1 d . . . C10 C -0.4791(4) 0.4740(10) 0.5142(3) 0.0213(16) Uani 1 1 d . . . H10 H -0.5264 0.4458 0.5209 0.026 Uiso 1 1 calc R . . C11 C -0.7541(4) -0.7249(10) 0.2919(3) 0.0211(16) Uani 1 1 d . . . H11 H -0.7228 -0.8577 0.3180 0.025 Uiso 1 1 calc R . . C12 C -0.6897(4) -0.5261(10) 0.3205(3) 0.0209(16) Uani 1 1 d . . . C13 C -0.6249(5) -0.4899(10) 0.3044(3) 0.0235(17) Uani 1 1 d . . . H13 H -0.6214 -0.5885 0.2761 0.028 Uiso 1 1 calc R . . C14 C -0.5673(4) -0.3152(10) 0.3288(3) 0.0208(16) Uani 1 1 d . . . C15 C -0.5731(4) -0.1773(10) 0.3730(3) 0.0208(15) Uani 1 1 d . . . C16 C -0.6390(4) -0.2278(10) 0.3867(3) 0.0231(16) Uani 1 1 d . . . C17 C -0.6490(4) -0.0881(10) 0.4285(3) 0.0238(16) Uani 1 1 d . . . H17 H -0.6931 -0.1205 0.4383 0.029 Uiso 1 1 calc R . . C18 C -0.5957(5) 0.0919(11) 0.4546(3) 0.0287(18) Uani 1 1 d . . . H18 H -0.6049 0.1859 0.4812 0.034 Uiso 1 1 calc R . . C19 C -0.5271(4) 0.1443(11) 0.4435(3) 0.0214(16) Uani 1 1 d . . . C20 C -0.5163(5) 0.0067(10) 0.4033(3) 0.0255(17) Uani 1 1 d . . . H20 H -0.4698 0.0362 0.3959 0.031 Uiso 1 1 calc R . . C21 C -0.4950(4) 0.7553(11) 0.6079(3) 0.0200(15) Uani 1 1 d . . . C22 C -0.5552(4) 0.9204(10) 0.6010(3) 0.0241(16) Uani 1 1 d . . . H22 H -0.5536 1.0603 0.5838 0.029 Uiso 1 1 calc R . . C23 C -0.6157(4) 0.8877(11) 0.6179(3) 0.0301(17) Uani 1 1 d . . . H23 H -0.6559 1.0028 0.6124 0.036 Uiso 1 1 calc R . . C24 C -0.6183(5) 0.6816(11) 0.6436(3) 0.0310(18) Uani 1 1 d . . . H24 H -0.6608 0.6557 0.6553 0.037 Uiso 1 1 calc R . . C25 C -0.5588(5) 0.5169(11) 0.6519(3) 0.0298(18) Uani 1 1 d . . . H25 H -0.5598 0.3786 0.6700 0.036 Uiso 1 1 calc R . . C26 C -0.4979(4) 0.5509(10) 0.6340(3) 0.0247(17) Uani 1 1 d . . . H26 H -0.4579 0.4355 0.6395 0.030 Uiso 1 1 calc R . . C27 C -0.5020(4) -0.2736(10) 0.3095(3) 0.0255(16) Uani 1 1 d . . . C28 C -0.4423(4) -0.4407(10) 0.3160(3) 0.0266(17) Uani 1 1 d . . . H28 H -0.4425 -0.5809 0.3336 0.032 Uiso 1 1 calc R . . C29 C -0.3834(5) -0.4007(11) 0.2966(3) 0.0298(17) Uani 1 1 d . . . H29 H -0.3427 -0.5135 0.3013 0.036 Uiso 1 1 calc R . . C30 C -0.3830(4) -0.2007(11) 0.2708(3) 0.0283(17) Uani 1 1 d . . . H30 H -0.3418 -0.1750 0.2580 0.034 Uiso 1 1 calc R . . C31 C -0.4421(5) -0.0348(11) 0.2632(3) 0.0267(17) Uani 1 1 d . . . H31 H -0.4425 0.1034 0.2444 0.032 Uiso 1 1 calc R . . C32 C -0.5014(5) -0.0742(10) 0.2837(3) 0.0235(16) Uani 1 1 d . . . H32 H -0.5415 0.0394 0.2794 0.028 Uiso 1 1 calc R . . C33 C -0.2188(4) 1.2543(10) 0.6952(3) 0.0267(16) Uani 1 1 d . . . C34 C -0.1760(5) 1.0926(10) 0.7424(3) 0.0269(16) Uani 1 1 d . . . H34 H -0.1665 0.9468 0.7321 0.032 Uiso 1 1 calc R . . C35 C -0.1480(5) 1.1442(13) 0.8032(3) 0.0363(18) Uani 1 1 d . . . H35 H -0.1178 1.0353 0.8346 0.044 Uiso 1 1 calc R . . C36 C -0.1635(5) 1.3518(13) 0.8186(4) 0.0390(19) Uani 1 1 d . . . H36 H -0.1428 1.3869 0.8607 0.047 Uiso 1 1 calc R . . C37 C -0.2078(5) 1.5071(13) 0.7744(4) 0.040(2) Uani 1 1 d . . . H37 H -0.2205 1.6478 0.7855 0.048 Uiso 1 1 calc R . . C38 C -0.2355(4) 1.4620(10) 0.7116(3) 0.0261(17) Uani 1 1 d . . . H38 H -0.2654 1.5733 0.6809 0.031 Uiso 1 1 calc R . . C39 C -0.1597(4) 1.1916(10) 0.6252(3) 0.0260(17) Uani 1 1 d . . . C40 C -0.1059(5) 1.0066(12) 0.6447(3) 0.0332(19) Uani 1 1 d . . . H40 H -0.1235 0.8767 0.6573 0.040 Uiso 1 1 calc R . . C41 C -0.0266(5) 1.0067(13) 0.6461(3) 0.0352(19) Uani 1 1 d . . . H41 H 0.0096 0.8776 0.6597 0.042 Uiso 1 1 calc R . . C42 C -0.0002(5) 1.1943(13) 0.6279(3) 0.041(2) Uani 1 1 d . . . H42 H 0.0537 1.1938 0.6283 0.050 Uiso 1 1 calc R . . C43 C -0.0529(5) 1.3836(12) 0.6090(3) 0.0341(18) Uani 1 1 d . . . H43 H -0.0353 1.5131 0.5963 0.041 Uiso 1 1 calc R . . C44 C -0.1309(5) 1.3830(12) 0.6088(3) 0.0318(18) Uani 1 1 d . . . H44 H -0.1656 1.5146 0.5973 0.038 Uiso 1 1 calc R . . C45 C -0.8365(4) -0.7016(10) 0.2941(3) 0.0259(17) Uani 1 1 d . . . C46 C -0.8877(5) -0.5060(12) 0.2747(3) 0.0293(18) Uani 1 1 d . . . H46 H -0.8674 -0.3788 0.2631 0.035 Uiso 1 1 calc R . . C47 C -0.9671(5) -0.4972(12) 0.2725(3) 0.0314(19) Uani 1 1 d . . . H47 H -1.0018 -0.3656 0.2583 0.038 Uiso 1 1 calc R . . C48 C -0.9961(5) -0.6780(12) 0.2908(3) 0.0336(18) Uani 1 1 d . . . H48 H -1.0507 -0.6717 0.2893 0.040 Uiso 1 1 calc R . . C49 C -0.9451(5) -0.8702(13) 0.3116(3) 0.0366(19) Uani 1 1 d . . . H49 H -0.9645 -0.9943 0.3250 0.044 Uiso 1 1 calc R . . C50 C -0.8667(4) -0.8820(11) 0.3128(3) 0.0281(17) Uani 1 1 d . . . H50 H -0.8329 -1.0150 0.3265 0.034 Uiso 1 1 calc R . . C51 C -0.7758(4) -0.7832(11) 0.2261(3) 0.0254(16) Uani 1 1 d . . . C52 C -0.8212(5) -0.6347(11) 0.1774(3) 0.0318(17) Uani 1 1 d . . . H52 H -0.8353 -0.4906 0.1856 0.038 Uiso 1 1 calc R . . C53 C -0.8463(5) -0.6919(12) 0.1175(3) 0.0360(18) Uani 1 1 d . . . H53 H -0.8776 -0.5885 0.0847 0.043 Uiso 1 1 calc R . . C54 C -0.8252(5) -0.9038(12) 0.1053(3) 0.0347(19) Uani 1 1 d . . . H54 H -0.8414 -0.9448 0.0642 0.042 Uiso 1 1 calc R . . C55 C -0.7813(5) -1.0506(11) 0.1529(3) 0.0300(17) Uani 1 1 d . . . H55 H -0.7675 -1.1953 0.1448 0.036 Uiso 1 1 calc R . . C56 C -0.7563(5) -0.9908(11) 0.2133(3) 0.0287(17) Uani 1 1 d . . . H56 H -0.7255 -1.0948 0.2460 0.034 Uiso 1 1 calc R . . C57 C -0.1659(5) 0.0789(11) 0.4722(4) 0.041(2) Uani 1 1 d . . . H57 H -0.1640 0.0789 0.5127 0.049 Uiso 1 1 calc R . . C58 C 0.1487(5) 0.4558(12) 0.4457(4) 0.045(2) Uani 1 1 d . . . H58 H 0.1409 0.4083 0.4050 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 0.118(2) 0.0575(14) 0.0668(14) 0.0082(13) 0.0500(15) -0.0050(15) Cl2 0.0613(16) 0.0875(18) 0.0540(14) -0.0145(13) 0.0211(12) -0.0185(13) Cl3 0.0665(16) 0.0779(17) 0.0589(14) -0.0119(12) 0.0256(12) 0.0048(13) Cl4 0.0746(16) 0.0696(15) 0.0579(13) -0.0040(12) 0.0339(12) -0.0145(12) Cl5 0.0604(16) 0.140(2) 0.0468(13) 0.0118(15) 0.0149(12) 0.0360(16) Cl6 0.117(2) 0.0375(12) 0.0801(15) -0.0029(12) 0.0647(15) -0.0017(12) N1 0.030(4) 0.025(3) 0.020(3) -0.003(3) 0.010(3) -0.004(3) N2 0.016(3) 0.022(3) 0.020(3) 0.000(2) 0.005(3) 0.000(2) C1 0.020(4) 0.021(4) 0.029(4) 0.000(3) 0.008(3) 0.006(3) C2 0.029(5) 0.019(4) 0.026(4) 0.003(3) 0.011(4) 0.002(3) C3 0.020(4) 0.023(4) 0.026(4) 0.000(3) 0.012(4) 0.003(3) C4 0.022(4) 0.025(4) 0.019(3) -0.001(3) 0.008(3) 0.001(3) C5 0.032(5) 0.014(4) 0.024(4) 0.003(3) 0.014(3) 0.005(3) C6 0.021(4) 0.021(4) 0.022(4) 0.004(3) 0.010(3) 0.001(3) C7 0.031(5) 0.027(4) 0.024(4) 0.000(3) 0.013(4) -0.003(3) C8 0.025(4) 0.024(4) 0.025(4) 0.000(3) 0.014(3) -0.003(3) C9 0.026(4) 0.032(4) 0.013(3) 0.003(3) 0.009(3) 0.006(3) C10 0.016(4) 0.024(4) 0.024(4) 0.002(3) 0.010(3) 0.000(3) C11 0.021(4) 0.017(3) 0.023(4) -0.006(3) 0.010(3) -0.005(3) C12 0.013(4) 0.025(4) 0.018(3) 0.001(3) 0.002(3) 0.001(3) C13 0.025(5) 0.024(4) 0.021(4) 0.002(3) 0.012(4) 0.004(3) C14 0.024(4) 0.016(4) 0.023(4) -0.001(3) 0.013(3) 0.002(3) C15 0.014(4) 0.023(4) 0.023(3) -0.003(3) 0.008(3) 0.001(3) C16 0.022(4) 0.023(4) 0.018(3) 0.003(3) 0.006(3) 0.003(3) C17 0.016(4) 0.030(4) 0.022(4) -0.001(3) 0.007(3) -0.001(3) C18 0.041(5) 0.025(4) 0.021(4) -0.002(3) 0.016(4) 0.008(3) C19 0.022(4) 0.022(4) 0.017(3) 0.000(3) 0.007(3) -0.005(3) C20 0.032(5) 0.018(3) 0.027(4) 0.001(3) 0.016(4) -0.001(3) C21 0.012(4) 0.030(4) 0.016(3) -0.012(3) 0.006(3) -0.006(3) C22 0.030(5) 0.017(4) 0.025(4) 0.000(3) 0.013(4) 0.004(3) C23 0.022(4) 0.029(4) 0.036(4) -0.002(3) 0.012(4) 0.007(3) C24 0.027(4) 0.033(5) 0.036(4) -0.003(3) 0.018(4) -0.005(3) C25 0.035(5) 0.026(4) 0.027(4) -0.002(3) 0.015(4) -0.006(3) C26 0.025(4) 0.015(4) 0.023(4) 0.000(3) 0.004(4) 0.005(3) C27 0.023(4) 0.026(4) 0.025(4) 0.000(3) 0.010(3) 0.001(3) C28 0.023(4) 0.021(4) 0.028(4) -0.004(3) 0.007(4) -0.001(3) C29 0.028(4) 0.034(4) 0.023(4) -0.003(3) 0.010(4) -0.003(3) C30 0.022(4) 0.040(5) 0.025(4) -0.001(3) 0.013(3) -0.001(3) C31 0.026(4) 0.026(4) 0.019(4) -0.004(3) 0.005(3) -0.004(3) C32 0.025(4) 0.027(4) 0.023(4) -0.006(3) 0.016(3) -0.003(3) C33 0.018(4) 0.023(4) 0.036(4) -0.002(3) 0.012(3) 0.000(3) C34 0.027(4) 0.024(4) 0.025(4) -0.004(3) 0.010(3) 0.001(3) C35 0.029(5) 0.049(5) 0.032(4) 0.002(4) 0.016(4) 0.002(4) C36 0.029(5) 0.049(5) 0.038(5) -0.005(4) 0.016(4) -0.015(4) C37 0.043(6) 0.040(5) 0.051(5) -0.014(4) 0.033(5) -0.017(4) C38 0.026(4) 0.019(4) 0.036(4) -0.001(3) 0.019(4) -0.001(3) C39 0.023(4) 0.029(4) 0.021(4) 0.005(3) 0.009(3) 0.001(3) C40 0.028(5) 0.034(4) 0.026(4) 0.000(3) 0.005(4) 0.001(4) C41 0.011(5) 0.053(5) 0.032(4) -0.006(4) 0.004(4) 0.004(3) C42 0.035(5) 0.045(5) 0.045(5) -0.009(4) 0.020(4) -0.006(4) C43 0.025(5) 0.041(5) 0.035(4) -0.006(4) 0.014(4) -0.004(4) C44 0.036(5) 0.028(4) 0.034(4) -0.004(3) 0.020(4) -0.006(3) C45 0.028(4) 0.022(4) 0.024(4) -0.002(3) 0.010(3) -0.005(3) C46 0.023(5) 0.039(4) 0.021(4) 0.003(3) 0.008(4) 0.001(3) C47 0.035(6) 0.034(4) 0.025(4) -0.008(3) 0.014(4) -0.004(3) C48 0.023(4) 0.046(5) 0.029(4) -0.006(4) 0.011(4) 0.001(4) C49 0.035(5) 0.042(5) 0.030(4) -0.014(4) 0.015(4) -0.018(4) C50 0.020(4) 0.027(4) 0.033(4) -0.001(3) 0.010(4) 0.003(3) C51 0.021(4) 0.030(4) 0.024(4) 0.000(3) 0.011(3) -0.005(3) C52 0.031(4) 0.029(4) 0.038(4) 0.002(3) 0.020(4) 0.007(3) C53 0.028(4) 0.046(5) 0.029(4) 0.005(4) 0.011(3) -0.002(4) C54 0.029(5) 0.055(5) 0.023(4) -0.008(4) 0.016(4) -0.009(4) C55 0.034(5) 0.033(4) 0.034(4) -0.009(3) 0.025(4) -0.005(3) C56 0.028(5) 0.022(4) 0.032(4) 0.001(3) 0.013(4) -0.002(3) C57 0.042(5) 0.030(4) 0.040(4) -0.003(3) 0.012(4) -0.004(4) C58 0.039(5) 0.057(5) 0.037(4) -0.001(4) 0.016(4) 0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C57 1.753(7) . ? Cl2 C57 1.717(8) . ? Cl3 C57 1.791(8) . ? Cl4 C58 1.728(8) . ? Cl5 C58 1.765(8) . ? Cl6 C58 1.751(7) . ? N1 C2 1.321(8) . ? N1 C6 1.393(8) . ? N2 C12 1.297(8) . ? N2 C16 1.380(8) . ? C1 C33 1.515(9) . ? C1 C2 1.524(9) . ? C1 C39 1.537(9) . ? C1 H1 1.0000 . ? C2 C3 1.410(9) . ? C3 C4 1.379(9) . ? C3 H3 0.9500 . ? C4 C5 1.440(8) . ? C4 C21 1.481(9) . ? C5 C6 1.405(9) . ? C5 C10 1.419(9) . ? C6 C7 1.393(9) . ? C7 C8 1.370(9) . ? C7 H7 0.9500 . ? C8 C9 1.412(9) . ? C8 H8 0.9500 . ? C9 C10 1.372(8) . ? C9 C19 1.494(8) . ? C10 H10 0.9500 . ? C11 C45 1.497(9) . ? C11 C51 1.534(8) . ? C11 C12 1.550(9) . ? C11 H11 1.0000 . ? C12 C13 1.415(9) . ? C13 C14 1.370(9) . ? C13 H13 0.9500 . ? C14 C15 1.428(8) . ? C14 C27 1.488(9) . ? C15 C16 1.410(8) . ? C15 C20 1.423(9) . ? C16 C17 1.423(9) . ? C17 C18 1.361(9) . ? C17 H17 0.9500 . ? C18 C19 1.415(9) . ? C18 H18 0.9500 . ? C19 C20 1.391(8) . ? C20 H20 0.9500 . ? C21 C22 1.399(8) . ? C21 C26 1.402(8) . ? C22 C23 1.355(9) . ? C22 H22 0.9500 . ? C23 C24 1.406(9) . ? C23 H23 0.9500 . ? C24 C25 1.381(9) . ? C24 H24 0.9500 . ? C25 C26 1.379(10) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C32 1.362(8) . ? C27 C28 1.405(9) . ? C28 C29 1.380(9) . ? C28 H28 0.9500 . ? C29 C30 1.364(9) . ? C29 H29 0.9500 . ? C30 C31 1.385(9) . ? C30 H30 0.9500 . ? C31 C32 1.408(9) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C38 1.389(8) . ? C33 C34 1.414(9) . ? C34 C35 1.377(9) . ? C34 H34 0.9500 . ? C35 C36 1.371(10) . ? C35 H35 0.9500 . ? C36 C37 1.350(10) . ? C36 H36 0.9500 . ? C37 C38 1.417(10) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C39 C40 1.379(9) . ? C39 C44 1.400(9) . ? C40 C41 1.389(10) . ? C40 H40 0.9500 . ? C41 C42 1.382(10) . ? C41 H41 0.9500 . ? C42 C43 1.391(10) . ? C42 H42 0.9500 . ? C43 C44 1.381(9) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C50 1.389(9) . ? C45 C46 1.408(9) . ? C46 C47 1.382(10) . ? C46 H46 0.9500 . ? C47 C48 1.375(9) . ? C47 H47 0.9500 . ? C48 C49 1.391(10) . ? C48 H48 0.9500 . ? C49 C50 1.377(9) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? C51 C56 1.371(9) . ? C51 C52 1.390(9) . ? C52 C53 1.378(9) . ? C52 H52 0.9500 . ? C53 C54 1.400(10) . ? C53 H53 0.9500 . ? C54 C55 1.365(9) . ? C54 H54 0.9500 . ? C55 C56 1.392(9) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C57 H57 1.0000 . ? C58 H58 1.0000 . ? 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 C6 117.2(6) . . ? C12 N2 C16 117.5(5) . . ? C33 C1 C2 113.8(5) . . ? C33 C1 C39 109.5(5) . . ? C2 C1 C39 114.5(5) . . ? C33 C1 H1 106.1 . . ? C2 C1 H1 106.1 . . ? C39 C1 H1 106.1 . . ? N1 C2 C3 122.8(6) . . ? N1 C2 C1 117.5(6) . . ? C3 C2 C1 119.6(6) . . ? C4 C3 C2 121.5(6) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 117.2(6) . . ? C3 C4 C21 119.6(6) . . ? C5 C4 C21 123.1(6) . . ? C6 C5 C10 119.4(6) . . ? C6 C5 C4 117.6(6) . . ? C10 C5 C4 122.9(6) . . ? N1 C6 C7 117.6(6) . . ? N1 C6 C5 123.6(6) . . ? C7 C6 C5 118.7(6) . . ? C8 C7 C6 120.7(6) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 122.0(6) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C10 C9 C8 117.4(6) . . ? C10 C9 C19 121.1(5) . . ? C8 C9 C19 121.4(5) . . ? C9 C10 C5 121.6(6) . . ? C9 C10 H10 119.2 . . ? C5 C10 H10 119.2 . . ? C45 C11 C51 110.4(5) . . ? C45 C11 C12 114.5(5) . . ? C51 C11 C12 113.2(5) . . ? C45 C11 H11 106.0 . . ? C51 C11 H11 106.0 . . ? C12 C11 H11 106.0 . . ? N2 C12 C13 123.0(6) . . ? N2 C12 C11 117.0(6) . . ? C13 C12 C11 120.0(6) . . ? C14 C13 C12 121.2(6) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 117.1(6) . . ? C13 C14 C27 120.6(6) . . ? C15 C14 C27 122.2(6) . . ? C16 C15 C20 118.9(6) . . ? C16 C15 C14 117.6(6) . . ? C20 C15 C14 123.5(6) . . ? N2 C16 C15 123.4(6) . . ? N2 C16 C17 117.5(6) . . ? C15 C16 C17 119.0(6) . . ? C18 C17 C16 120.2(6) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 122.5(6) . . ? C17 C18 H18 118.7 . . ? C19 C18 H18 118.7 . . ? C20 C19 C18 117.5(6) . . ? C20 C19 C9 121.5(5) . . ? C18 C19 C9 121.0(5) . . ? C19 C20 C15 121.7(6) . . ? C19 C20 H20 119.2 . . ? C15 C20 H20 119.2 . . ? C22 C21 C26 117.9(6) . . ? C22 C21 C4 120.6(6) . . ? C26 C21 C4 121.5(6) . . ? C23 C22 C21 122.3(6) . . ? C23 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C22 C23 C24 119.3(6) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C25 C24 C23 119.6(6) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C26 C25 C24 120.8(6) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C21 120.1(6) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C32 C27 C28 119.5(6) . . ? C32 C27 C14 119.9(6) . . ? C28 C27 C14 120.6(6) . . ? C29 C28 C27 119.8(6) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C30 C29 C28 120.5(7) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C29 C30 C31 120.6(7) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C30 C31 C32 118.9(6) . . ? C30 C31 H31 120.6 . . ? C32 C31 H31 120.6 . . ? C27 C32 C31 120.7(6) . . ? C27 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C38 C33 C34 118.0(6) . . ? C38 C33 C1 121.0(6) . . ? C34 C33 C1 121.0(6) . . ? C35 C34 C33 120.7(6) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C36 C35 C34 120.3(7) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.9 . . ? C37 C36 C35 120.6(7) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C36 C37 C38 120.6(7) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C33 C38 C37 119.7(7) . . ? C33 C38 H38 120.2 . . ? C37 C38 H38 120.2 . . ? C40 C39 C44 118.2(7) . . ? C40 C39 C1 122.3(6) . . ? C44 C39 C1 119.1(6) . . ? C39 C40 C41 121.2(7) . . ? C39 C40 H40 119.4 . . ? C41 C40 H40 119.4 . . ? C42 C41 C40 120.2(7) . . ? C42 C41 H41 119.9 . . ? C40 C41 H41 119.9 . . ? C41 C42 C43 119.5(7) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? C44 C43 C42 119.9(7) . . ? C44 C43 H43 120.1 . . ? C42 C43 H43 120.1 . . ? C43 C44 C39 121.1(7) . . ? C43 C44 H44 119.5 . . ? C39 C44 H44 119.5 . . ? C50 C45 C46 118.2(7) . . ? C50 C45 C11 119.4(6) . . ? C46 C45 C11 122.3(6) . . ? C47 C46 C45 120.7(7) . . ? C47 C46 H46 119.7 . . ? C45 C46 H46 119.7 . . ? C48 C47 C46 120.3(7) . . ? C48 C47 H47 119.9 . . ? C46 C47 H47 119.9 . . ? C47 C48 C49 119.6(7) . . ? C47 C48 H48 120.2 . . ? C49 C48 H48 120.2 . . ? C50 C49 C48 120.5(7) . . ? C50 C49 H49 119.8 . . ? C48 C49 H49 119.8 . . ? C49 C50 C45 120.8(7) . . ? C49 C50 H50 119.6 . . ? C45 C50 H50 119.6 . . ? C56 C51 C52 118.4(6) . . ? C56 C51 C11 120.3(6) . . ? C52 C51 C11 121.1(6) . . ? C53 C52 C51 121.4(6) . . ? C53 C52 H52 119.3 . . ? C51 C52 H52 119.3 . . ? C52 C53 C54 119.4(7) . . ? C52 C53 H53 120.3 . . ? C54 C53 H53 120.3 . . ? C55 C54 C53 119.2(6) . . ? C55 C54 H54 120.4 . . ? C53 C54 H54 120.4 . . ? C54 C55 C56 120.8(6) . . ? C54 C55 H55 119.6 . . ? C56 C55 H55 119.6 . . ? C51 C56 C55 120.7(6) . . ? C51 C56 H56 119.7 . . ? C55 C56 H56 119.7 . . ? Cl2 C57 Cl1 110.5(4) . . ? Cl2 C57 Cl3 109.5(4) . . ? Cl1 C57 Cl3 109.2(4) . . ? Cl2 C57 H57 109.2 . . ? Cl1 C57 H57 109.2 . . ? Cl3 C57 H57 109.2 . . ? Cl4 C58 Cl6 111.0(4) . . ? Cl4 C58 Cl5 110.1(4) . . ? Cl6 C58 Cl5 109.8(4) . . ? Cl4 C58 H58 108.6 . . ? Cl6 C58 H58 108.6 . . ? Cl5 C58 H58 108.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 -1.8(9) . . . . ? C6 N1 C2 C1 -177.8(5) . . . . ? C33 C1 C2 N1 -146.7(6) . . . . ? C39 C1 C2 N1 -19.7(8) . . . . ? C33 C1 C2 C3 37.2(8) . . . . ? C39 C1 C2 C3 164.1(6) . . . . ? N1 C2 C3 C4 1.9(10) . . . . ? C1 C2 C3 C4 177.8(5) . . . . ? C2 C3 C4 C5 -0.3(9) . . . . ? C2 C3 C4 C21 175.4(6) . . . . ? C3 C4 C5 C6 -1.1(8) . . . . ? C21 C4 C5 C6 -176.6(6) . . . . ? C3 C4 C5 C10 -178.7(6) . . . . ? C21 C4 C5 C10 5.7(9) . . . . ? C2 N1 C6 C7 -177.7(6) . . . . ? C2 N1 C6 C5 0.3(9) . . . . ? C10 C5 C6 N1 178.9(5) . . . . ? C4 C5 C6 N1 1.2(9) . . . . ? C10 C5 C6 C7 -3.1(9) . . . . ? C4 C5 C6 C7 179.1(5) . . . . ? N1 C6 C7 C8 177.3(6) . . . . ? C5 C6 C7 C8 -0.8(9) . . . . ? C6 C7 C8 C9 4.3(10) . . . . ? C7 C8 C9 C10 -3.7(9) . . . . ? C7 C8 C9 C19 177.8(5) . . . . ? C8 C9 C10 C5 -0.4(9) . . . . ? C19 C9 C10 C5 178.1(5) . . . . ? C6 C5 C10 C9 3.8(9) . . . . ? C4 C5 C10 C9 -178.6(6) . . . . ? C16 N2 C12 C13 0.4(9) . . . . ? C16 N2 C12 C11 178.7(5) . . . . ? C45 C11 C12 N2 22.0(8) . . . . ? C51 C11 C12 N2 149.8(6) . . . . ? C45 C11 C12 C13 -159.6(6) . . . . ? C51 C11 C12 C13 -31.9(8) . . . . ? N2 C12 C13 C14 -1.9(10) . . . . ? C11 C12 C13 C14 179.8(6) . . . . ? C12 C13 C14 C15 2.5(9) . . . . ? C12 C13 C14 C27 -177.4(6) . . . . ? C13 C14 C15 C16 -1.7(8) . . . . ? C27 C14 C15 C16 178.2(6) . . . . ? C13 C14 C15 C20 178.5(6) . . . . ? C27 C14 C15 C20 -1.6(9) . . . . ? C12 N2 C16 C15 0.4(9) . . . . ? C12 N2 C16 C17 178.0(6) . . . . ? C20 C15 C16 N2 -179.9(6) . . . . ? C14 C15 C16 N2 0.3(9) . . . . ? C20 C15 C16 C17 2.5(9) . . . . ? C14 C15 C16 C17 -177.4(6) . . . . ? N2 C16 C17 C18 -177.6(6) . . . . ? C15 C16 C17 C18 0.2(9) . . . . ? C16 C17 C18 C19 -2.2(10) . . . . ? C17 C18 C19 C20 1.3(9) . . . . ? C17 C18 C19 C9 -177.8(5) . . . . ? C10 C9 C19 C20 179.9(7) . . . . ? C8 C9 C19 C20 -1.6(8) . . . . ? C10 C9 C19 C18 -1.0(8) . . . . ? C8 C9 C19 C18 177.5(7) . . . . ? C18 C19 C20 C15 1.5(9) . . . . ? C9 C19 C20 C15 -179.4(5) . . . . ? C16 C15 C20 C19 -3.4(9) . . . . ? C14 C15 C20 C19 176.4(6) . . . . ? C3 C4 C21 C22 59.6(8) . . . . ? C5 C4 C21 C22 -124.9(6) . . . . ? C3 C4 C21 C26 -120.3(6) . . . . ? C5 C4 C21 C26 55.2(8) . . . . ? C26 C21 C22 C23 -0.7(9) . . . . ? C4 C21 C22 C23 179.4(6) . . . . ? C21 C22 C23 C24 0.3(10) . . . . ? C22 C23 C24 C25 0.7(10) . . . . ? C23 C24 C25 C26 -1.2(10) . . . . ? C24 C25 C26 C21 0.8(10) . . . . ? C22 C21 C26 C25 0.1(9) . . . . ? C4 C21 C26 C25 -180.0(6) . . . . ? C13 C14 C27 C32 121.3(7) . . . . ? C15 C14 C27 C32 -58.6(9) . . . . ? C13 C14 C27 C28 -56.8(8) . . . . ? C15 C14 C27 C28 123.3(6) . . . . ? C32 C27 C28 C29 0.5(9) . . . . ? C14 C27 C28 C29 178.7(6) . . . . ? C27 C28 C29 C30 -0.5(10) . . . . ? C28 C29 C30 C31 -0.4(9) . . . . ? C29 C30 C31 C32 1.3(9) . . . . ? C28 C27 C32 C31 0.3(10) . . . . ? C14 C27 C32 C31 -177.9(6) . . . . ? C30 C31 C32 C27 -1.2(10) . . . . ? C2 C1 C33 C38 -122.4(7) . . . . ? C39 C1 C33 C38 108.1(7) . . . . ? C2 C1 C33 C34 59.5(8) . . . . ? C39 C1 C33 C34 -70.0(8) . . . . ? C38 C33 C34 C35 -3.2(10) . . . . ? C1 C33 C34 C35 175.0(6) . . . . ? C33 C34 C35 C36 1.9(11) . . . . ? C34 C35 C36 C37 1.3(11) . . . . ? C35 C36 C37 C38 -3.1(11) . . . . ? C34 C33 C38 C37 1.5(10) . . . . ? C1 C33 C38 C37 -176.7(6) . . . . ? C36 C37 C38 C33 1.6(10) . . . . ? C33 C1 C39 C40 77.8(7) . . . . ? C2 C1 C39 C40 -51.3(8) . . . . ? C33 C1 C39 C44 -93.9(7) . . . . ? C2 C1 C39 C44 136.9(6) . . . . ? C44 C39 C40 C41 -2.0(10) . . . . ? C1 C39 C40 C41 -173.8(6) . . . . ? C39 C40 C41 C42 0.0(11) . . . . ? C40 C41 C42 C43 1.0(11) . . . . ? C41 C42 C43 C44 0.2(10) . . . . ? C42 C43 C44 C39 -2.3(10) . . . . ? C40 C39 C44 C43 3.2(10) . . . . ? C1 C39 C44 C43 175.3(6) . . . . ? C51 C11 C45 C50 96.1(7) . . . . ? C12 C11 C45 C50 -134.7(6) . . . . ? C51 C11 C45 C46 -80.4(7) . . . . ? C12 C11 C45 C46 48.7(8) . . . . ? C50 C45 C46 C47 -2.1(9) . . . . ? C11 C45 C46 C47 174.5(6) . . . . ? C45 C46 C47 C48 1.7(10) . . . . ? C46 C47 C48 C49 0.0(10) . . . . ? C47 C48 C49 C50 -1.2(10) . . . . ? C48 C49 C50 C45 0.8(10) . . . . ? C46 C45 C50 C49 0.8(9) . . . . ? C11 C45 C50 C49 -175.9(6) . . . . ? C45 C11 C51 C56 -110.6(7) . . . . ? C12 C11 C51 C56 119.6(7) . . . . ? C45 C11 C51 C52 64.5(8) . . . . ? C12 C11 C51 C52 -65.4(8) . . . . ? C56 C51 C52 C53 -0.2(10) . . . . ? C11 C51 C52 C53 -175.4(6) . . . . ? C51 C52 C53 C54 -0.3(11) . . . . ? C52 C53 C54 C55 0.9(10) . . . . ? C53 C54 C55 C56 -0.9(11) . . . . ? C52 C51 C56 C55 0.2(10) . . . . ? C11 C51 C56 C55 175.4(6) . . . . ? C54 C55 C56 C51 0.3(11) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.731 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.082