# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Brad Holliday' _publ_contact_author_email BHOLLIDAY@CM.UTEXAS.EDU _publ_section_title ; Synthesis, Characterization, and Photophysical Properties of a Thiophene-Functionalized Bis(pyrazolyl) Pyridine (BPP) Tricarbonyl Rhenium(I) Complex ; loop_ _publ_author_name L.Lytwak M.Mejia J.M.Stanley B.J.Holliday # Attachment '- Complex 1 (CCDC 764347).cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 764347' #TrackingRef '- Complex 1 (CCDC 764347).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H17 N5 S2, Re, Br, 3 C O' _chemical_formula_sum 'C24 H17 Br N5 O3 Re S2' _chemical_formula_weight 753.66 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.664(2) _cell_length_b 9.8970(10) _cell_length_c 17.330(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.493(2) _cell_angle_gamma 90.00 _cell_volume 2455.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 19278 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description yellow _exptl_crystal_colour prisms _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.039 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 6.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.385 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Abscor. T. Higashi (2001). The Rigaku Corporation. Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC-12 with Saturn 724+ CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22033 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0089 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 27.50 _reflns_number_total 22036 _reflns_number_gt 20518 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Cooper, R. I., Gould, R. O., Parsons, S. and Watkin, D. J. (2002). ROTAX. J. Applied Cryst. 35, 168-174. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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. The data crystal was twinned. The twin law was determined using TwinSolve (Rigaku Corporation, Tokyo, Japan). The twin resulted from a 180 degree rotation about the 101 direct lattice direction with twin matrix [-0.21, 0, 0.79; 0, -1, 0; 1.21, 0, 0.21]. The twin fraction refined to 0.288(1). ; _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^)+(0.0703P)^2^+14.6569P] 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 22036 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1896 _refine_ls_wR_factor_gt 0.1840 _refine_ls_goodness_of_fit_ref 1.843 _refine_ls_restrained_S_all 1.843 _refine_ls_shift/su_max 0.002 _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 Re1 Re -0.033379(15) -0.07429(2) 0.747913(13) 0.01745(8) Uani 1 1 d . . . Br1 Br 0.06161(4) -0.22269(6) 0.66756(3) 0.02367(14) Uani 1 1 d . . . S1 S 0.37352(13) -0.0116(2) 1.04639(11) 0.0372(4) Uani 1 1 d . . . S2 S -0.40090(11) -0.02452(19) 0.46436(11) 0.0316(4) Uani 1 1 d . . . O1 O -0.1417(3) 0.1081(5) 0.8388(3) 0.0324(11) Uani 1 1 d . . . O2 O 0.1060(3) -0.1485(4) 0.9023(3) 0.0284(10) Uani 1 1 d . . . O3 O -0.1462(3) -0.3138(5) 0.7878(3) 0.0276(10) Uani 1 1 d . . . N1 N 0.1289(3) 0.1534(5) 0.9518(3) 0.0228(11) Uani 1 1 d . . . N2 N 0.0841(3) 0.1665(5) 0.8756(3) 0.0211(10) Uani 1 1 d . . . N3 N 0.0475(3) 0.0958(5) 0.7071(3) 0.0161(9) Uani 1 1 d . . . N4 N -0.1110(3) -0.0185(5) 0.6334(3) 0.0203(10) Uani 1 1 d . . . N5 N -0.1947(3) -0.0539(5) 0.5858(3) 0.0194(10) Uani 1 1 d . . . C1 C 0.4133(5) 0.0265(8) 1.1437(4) 0.0368(16) Uani 1 1 d . . . H1 H 0.4661 -0.0161 1.1760 0.044 Uiso 1 1 calc R . . C2 C 0.3625(4) 0.1237(8) 1.1711(4) 0.0301(14) Uani 1 1 d . . . H2 H 0.3754 0.1575 1.2237 0.036 Uiso 1 1 calc R . . C3 C 0.2876(5) 0.1674(7) 1.1096(4) 0.0290(14) Uani 1 1 d . . . H3 H 0.2434 0.2336 1.1172 0.035 Uiso 1 1 calc R . . C4 C 0.2848(4) 0.1047(7) 1.0375(4) 0.0237(13) Uani 1 1 d . . . C5 C 0.2210(4) 0.1246(6) 0.9608(3) 0.0208(12) Uani 1 1 d . . . C6 C 0.2369(4) 0.1201(6) 0.8847(3) 0.0204(12) Uani 1 1 d . . . H6 H 0.2947 0.1045 0.8699 0.025 Uiso 1 1 calc R . . C7 C 0.1509(4) 0.1429(6) 0.8350(3) 0.0206(12) Uani 1 1 d . . . C8 C 0.1260(4) 0.1557(6) 0.7473(3) 0.0189(11) Uani 1 1 d . . . C9 C 0.1821(4) 0.2336(6) 0.7089(4) 0.0236(13) Uani 1 1 d . . . H9 H 0.2390 0.2704 0.7381 0.028 Uiso 1 1 calc R . . C10 C 0.1556(4) 0.2573(6) 0.6293(4) 0.0231(13) Uani 1 1 d . . . H10 H 0.1945 0.3081 0.6028 0.028 Uiso 1 1 calc R . . C11 C 0.0720(4) 0.2066(6) 0.5884(3) 0.0204(12) Uani 1 1 d . . . H11 H 0.0503 0.2269 0.5339 0.024 Uiso 1 1 calc R . . C12 C 0.0192(4) 0.1246(6) 0.6279(3) 0.0191(11) Uani 1 1 d . . . C13 C -0.0697(4) 0.0666(6) 0.5891(3) 0.0175(11) Uani 1 1 d . . . C14 C -0.1267(4) 0.0827(6) 0.5145(4) 0.0195(12) Uani 1 1 d . . . H14 H -0.1132 0.1353 0.4724 0.023 Uiso 1 1 calc R . . C15 C -0.2073(4) 0.0076(6) 0.5127(4) 0.0233(13) Uani 1 1 d . . . C16 C -0.2883(4) -0.0020(6) 0.4511(4) 0.0225(12) Uani 1 1 d . . . C17 C -0.2928(4) 0.0151(7) 0.3690(4) 0.0265(13) Uani 1 1 d . . . H17 H -0.2393 0.0309 0.3476 0.032 Uiso 1 1 calc R . . C18 C -0.3806(5) 0.0067(7) 0.3241(4) 0.0329(15) Uani 1 1 d . . . H18 H -0.3940 0.0140 0.2682 0.039 Uiso 1 1 calc R . . C19 C -0.4484(5) -0.0132(7) 0.3664(4) 0.0333(15) Uani 1 1 d . . . H19 H -0.5134 -0.0198 0.3438 0.040 Uiso 1 1 calc R . . C20 C -0.2524(5) -0.1559(7) 0.6124(4) 0.0319(15) Uani 1 1 d . . . H20A H -0.2252 -0.1797 0.6674 0.048 Uiso 1 1 calc R . . H20B H -0.2554 -0.2365 0.5791 0.048 Uiso 1 1 calc R . . H20C H -0.3155 -0.1201 0.6086 0.048 Uiso 1 1 calc R . . C21 C 0.0740(5) 0.1638(7) 1.0125(4) 0.0303(15) Uani 1 1 d . . . H21A H 0.0089 0.1846 0.9876 0.045 Uiso 1 1 calc R . . H21B H 0.0995 0.2359 1.0497 0.045 Uiso 1 1 calc R . . H21C H 0.0767 0.0778 1.0410 0.045 Uiso 1 1 calc R . . C22 C -0.1040(4) -0.2238(6) 0.7717(3) 0.0200(12) Uani 1 1 d . . . C23 C 0.0530(4) -0.1164(6) 0.8430(3) 0.0189(11) Uani 1 1 d . . . C24 C -0.1007(4) 0.0429(7) 0.8039(3) 0.0245(13) Uani 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 Re1 0.01830(12) 0.01790(14) 0.01831(12) 0.00289(8) 0.00868(8) 0.00070(8) Br1 0.0263(3) 0.0231(3) 0.0252(3) 0.0024(2) 0.0135(2) 0.0036(2) S1 0.0363(9) 0.0364(11) 0.0354(9) -0.0104(8) 0.0003(7) 0.0099(8) S2 0.0210(7) 0.0341(10) 0.0396(9) -0.0010(8) 0.0063(7) -0.0021(7) O1 0.035(2) 0.027(3) 0.042(3) -0.001(2) 0.022(2) 0.007(2) O2 0.033(2) 0.021(2) 0.032(2) -0.0011(19) 0.011(2) -0.0059(19) O3 0.027(2) 0.025(2) 0.035(2) 0.005(2) 0.0162(19) -0.0011(19) N1 0.024(2) 0.024(3) 0.022(2) -0.006(2) 0.009(2) 0.000(2) N2 0.023(2) 0.023(3) 0.016(2) 0.001(2) 0.0034(18) -0.001(2) N3 0.021(2) 0.014(2) 0.016(2) 0.0030(18) 0.0096(18) 0.0038(18) N4 0.014(2) 0.029(3) 0.019(2) -0.001(2) 0.0047(18) -0.003(2) N5 0.024(2) 0.025(3) 0.007(2) 0.0026(18) -0.0008(17) -0.0007(19) C1 0.042(4) 0.039(4) 0.027(3) 0.005(3) 0.001(3) 0.003(3) C2 0.026(3) 0.040(4) 0.025(3) 0.002(3) 0.006(2) -0.006(3) C3 0.037(3) 0.029(4) 0.024(3) -0.004(3) 0.013(3) -0.001(3) C4 0.023(3) 0.023(3) 0.025(3) 0.001(2) 0.004(2) -0.001(2) C5 0.027(3) 0.014(3) 0.024(3) 0.004(2) 0.010(2) -0.004(2) C6 0.023(3) 0.017(3) 0.021(3) 0.001(2) 0.007(2) -0.003(2) C7 0.019(3) 0.023(3) 0.022(3) 0.001(2) 0.008(2) -0.006(2) C8 0.020(3) 0.018(3) 0.021(3) 0.001(2) 0.009(2) -0.001(2) C9 0.022(3) 0.025(3) 0.025(3) -0.001(3) 0.007(2) -0.004(2) C10 0.027(3) 0.021(3) 0.025(3) 0.004(3) 0.014(3) 0.000(2) C11 0.024(3) 0.021(3) 0.018(3) 0.002(2) 0.009(2) -0.001(2) C12 0.018(3) 0.015(3) 0.027(3) 0.002(2) 0.011(2) -0.001(2) C13 0.019(3) 0.015(3) 0.021(3) 0.003(2) 0.010(2) 0.003(2) C14 0.022(3) 0.015(3) 0.024(3) 0.003(2) 0.011(2) 0.001(2) C15 0.024(3) 0.022(3) 0.025(3) 0.001(3) 0.010(2) 0.002(2) C16 0.023(3) 0.023(3) 0.021(3) -0.001(2) 0.004(2) 0.003(2) C17 0.029(3) 0.029(4) 0.022(3) 0.010(3) 0.005(2) 0.008(3) C18 0.040(4) 0.024(4) 0.030(3) -0.003(3) -0.004(3) -0.007(3) C19 0.029(3) 0.021(4) 0.041(4) 0.000(3) -0.011(3) -0.005(3) C20 0.037(3) 0.026(4) 0.033(3) 0.010(3) 0.008(3) -0.014(3) C21 0.041(4) 0.033(4) 0.023(3) 0.005(3) 0.020(3) 0.008(3) C22 0.021(3) 0.021(3) 0.019(3) 0.005(2) 0.008(2) 0.006(2) C23 0.021(3) 0.014(3) 0.023(3) -0.001(2) 0.009(2) -0.001(2) C24 0.025(3) 0.031(4) 0.019(3) 0.000(3) 0.008(2) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C23 1.895(6) . ? Re1 C22 1.902(6) . ? Re1 C24 1.917(6) . ? Re1 N4 2.135(5) . ? Re1 N3 2.259(4) . ? Re1 Br1 2.6222(6) . ? S1 C1 1.704(7) . ? S1 C4 1.719(6) . ? S2 C19 1.694(7) . ? S2 C16 1.730(6) . ? O1 C24 1.141(7) . ? O2 C23 1.190(7) . ? O3 C22 1.153(7) . ? N1 N2 1.347(7) . ? N1 C5 1.356(7) . ? N1 C21 1.460(7) . ? N2 C7 1.343(7) . ? N3 C8 1.348(7) . ? N3 C12 1.375(7) . ? N4 C13 1.366(7) . ? N4 N5 1.369(6) . ? N5 C15 1.381(7) . ? N5 C20 1.454(7) . ? C1 C2 1.363(10) . ? C1 H1 0.9500 . ? C2 C3 1.423(9) . ? C2 H2 0.9500 . ? C3 C4 1.388(9) . ? C3 H3 0.9500 . ? C4 C5 1.463(9) . ? C5 C6 1.389(8) . ? C6 C7 1.383(8) . ? C6 H6 0.9500 . ? C7 C8 1.491(8) . ? C8 C9 1.397(7) . ? C9 C10 1.370(8) . ? C9 H9 0.9500 . ? C10 C11 1.371(8) . ? C10 H10 0.9500 . ? C11 C12 1.399(7) . ? C11 H11 0.9500 . ? C12 C13 1.450(8) . ? C13 C14 1.390(8) . ? C14 C15 1.391(8) . ? C14 H14 0.9500 . ? C15 C16 1.418(9) . ? C16 C17 1.420(8) . ? C17 C18 1.355(9) . ? C17 H17 0.9500 . ? C18 C19 1.371(9) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 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 C23 Re1 C22 86.2(2) . . ? C23 Re1 C24 90.8(3) . . ? C22 Re1 C24 89.8(2) . . ? C23 Re1 N4 170.6(2) . . ? C22 Re1 N4 101.3(2) . . ? C24 Re1 N4 94.9(2) . . ? C23 Re1 N3 98.0(2) . . ? C22 Re1 N3 174.3(2) . . ? C24 Re1 N3 94.0(2) . . ? N4 Re1 N3 74.14(18) . . ? C23 Re1 Br1 90.38(17) . . ? C22 Re1 Br1 93.20(16) . . ? C24 Re1 Br1 176.81(19) . . ? N4 Re1 Br1 83.62(13) . . ? N3 Re1 Br1 82.87(11) . . ? C1 S1 C4 91.8(3) . . ? C19 S2 C16 93.2(3) . . ? N2 N1 C5 113.3(4) . . ? N2 N1 C21 118.2(5) . . ? C5 N1 C21 128.4(5) . . ? C7 N2 N1 103.9(4) . . ? C8 N3 C12 117.7(5) . . ? C8 N3 Re1 127.8(4) . . ? C12 N3 Re1 113.7(4) . . ? C13 N4 N5 105.5(5) . . ? C13 N4 Re1 118.0(4) . . ? N5 N4 Re1 136.3(4) . . ? N4 N5 C15 111.4(5) . . ? N4 N5 C20 119.6(5) . . ? C15 N5 C20 128.7(5) . . ? C2 C1 S1 113.9(5) . . ? C2 C1 H1 123.1 . . ? S1 C1 H1 123.1 . . ? C1 C2 C3 110.2(6) . . ? C1 C2 H2 124.9 . . ? C3 C2 H2 124.9 . . ? C4 C3 C2 113.9(6) . . ? C4 C3 H3 123.0 . . ? C2 C3 H3 123.0 . . ? C3 C4 C5 130.2(6) . . ? C3 C4 S1 110.2(5) . . ? C5 C4 S1 119.7(5) . . ? N1 C5 C6 105.3(5) . . ? N1 C5 C4 124.0(5) . . ? C6 C5 C4 130.7(5) . . ? C7 C6 C5 105.6(5) . . ? C7 C6 H6 127.2 . . ? C5 C6 H6 127.2 . . ? N2 C7 C6 111.8(5) . . ? N2 C7 C8 118.3(5) . . ? C6 C7 C8 129.6(5) . . ? N3 C8 C9 121.5(5) . . ? N3 C8 C7 118.9(5) . . ? C9 C8 C7 119.6(5) . . ? C10 C9 C8 120.4(6) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 119.1(5) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 119.1(5) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N3 C12 C11 122.0(5) . . ? N3 C12 C13 115.3(5) . . ? C11 C12 C13 122.7(5) . . ? N4 C13 C14 110.1(5) . . ? N4 C13 C12 116.6(5) . . ? C14 C13 C12 133.3(5) . . ? C13 C14 C15 107.2(5) . . ? C13 C14 H14 126.4 . . ? C15 C14 H14 126.4 . . ? N5 C15 C14 105.8(5) . . ? N5 C15 C16 125.8(5) . . ? C14 C15 C16 128.4(6) . . ? C15 C16 C17 126.6(5) . . ? C15 C16 S2 125.2(4) . . ? C17 C16 S2 108.0(5) . . ? C18 C17 C16 113.5(6) . . ? C18 C17 H17 123.2 . . ? C16 C17 H17 123.2 . . ? C17 C18 C19 114.3(6) . . ? C17 C18 H18 122.8 . . ? C19 C18 H18 122.8 . . ? C18 C19 S2 110.9(5) . . ? C18 C19 H19 124.6 . . ? S2 C19 H19 124.6 . . ? N5 C20 H20A 109.5 . . ? N5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N1 C21 H21A 109.5 . . ? N1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O3 C22 Re1 178.6(5) . . ? O2 C23 Re1 177.2(5) . . ? O1 C24 Re1 177.2(6) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 3.192 _refine_diff_density_min -2.645 _refine_diff_density_rms 0.308 # Attachment '- Ligand (CCDC 772116).cif' data_shelxl_2 _database_code_depnum_ccdc_archive 'CCDC 772116' #TrackingRef '- Ligand (CCDC 772116).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H17 N5 S2' _chemical_formula_sum 'C21 H17 N5 S2' _chemical_formula_weight 403.52 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.045(2) _cell_length_b 10.104(2) _cell_length_c 20.422(4) _cell_angle_alpha 100.221(8) _cell_angle_beta 101.683(9) _cell_angle_gamma 91.634(8) _cell_volume 1993.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 10240 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8326 _exptl_absorpt_correction_T_max 0.9172 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (2008). SHELXL-97. Acat Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _diffrn_ambient_temperature 233(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCX-Mini with Mercury CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28171 _diffrn_reflns_av_R_equivalents 0.0916 _diffrn_reflns_av_sigmaI/netI 0.0783 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8946 _reflns_number_gt 6903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear 1.40 (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear 1.40 (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear 1.40 (Rigaku Inc., 2008)' _computing_structure_solution ;SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XL SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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. One of the thiophene groups was disordered by rotation about about the pyrazol carbon, C24A, to thiophene ring carbon, C1AA, bond. The disorder was modeled by assinging the variable x to the site occupancy factor of the atoms in one orientation, S1AA, C1AA, C2AA, C3AA, C4AA, and (1-x) to the site occupancy factor of the alternate orientation composed of S1AB, C1AB, C2AB, C3AB and C4AB. A common isotropic displacement parameter was refined for the atoms of the ring while geometric restraints were applied throughout the refinement. In this way, the site occupancy factor for atoms S1AA, C1AA, C2AA, C3AA, C4AA refined to 56(2)%. The atoms of the major component and the minor component were refined anisotropically while restraining their displacement parameters to be approximately isotropic. The other three thiophene rings were refined in a similar manner. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+2.0873P] 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 8946 _refine_ls_number_parameters 635 _refine_ls_number_restraints 825 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1781 _refine_ls_wR_factor_gt 0.1668 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.061 _refine_ls_shift/su_mean 0.002 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 N6 N 0.1494(2) 0.2702(2) 0.64872(10) 0.0291(4) Uani 1 1 d . . . N7 N 0.2325(3) -0.0698(2) 0.58693(11) 0.0399(5) Uani 1 1 d . . . N8 N 0.2578(2) 0.26672(19) 0.85160(10) 0.0292(4) Uani 1 1 d . . . N9 N 0.0340(2) 0.6900(2) 0.72559(12) 0.0385(5) Uani 1 1 d . . . C1 C 0.1637(3) 0.2344(2) 0.88530(12) 0.0308(5) Uani 1 1 d . . . N11 N -0.0704(2) 0.1428(2) 0.87111(11) 0.0368(5) Uani 1 1 d . . . N12 N 0.6654(2) 0.4198(2) 0.82569(13) 0.0411(5) Uani 1 1 d . . . N13 N 0.0326(3) 0.6082(2) 0.66510(12) 0.0387(5) Uani 1 1 d . . . N14 N -0.1779(2) 0.1053(2) 0.81801(11) 0.0360(5) Uani 1 1 d . . . N1 N 0.2881(3) -0.1519(2) 0.62952(12) 0.0394(5) Uani 1 1 d . . . N2 N 0.6086(2) 0.3929(2) 0.87730(12) 0.0400(5) Uani 1 1 d . . . C18 C 0.0289(3) 0.1854(2) 0.84324(12) 0.0294(5) Uani 1 1 d . . . C19 C 0.0942(3) 0.3788(3) 0.62775(12) 0.0326(5) Uani 1 1 d . . . C22 C 0.3829(3) 0.3128(2) 0.88752(13) 0.0330(5) Uani 1 1 d . . . C23 C 0.1579(3) 0.1616(3) 0.60127(12) 0.0330(5) Uani 1 1 d . . . C26 C 0.1169(3) 0.5025(2) 0.75167(13) 0.0315(5) Uani 1 1 d . . . H26 H 0.1542 0.4358 0.7753 0.038 Uiso 1 1 calc R . . C27 C 0.2166(3) 0.0453(2) 0.62850(13) 0.0324(5) Uani 1 1 d . . . C30 C 0.0832(3) 0.4939(2) 0.68129(13) 0.0318(5) Uani 1 1 d . . . C33 C 0.2616(3) 0.0367(2) 0.69694(13) 0.0318(5) Uani 1 1 d . . . H33 H 0.2610 0.1037 0.7352 0.038 Uiso 1 1 calc R . . C35 C 0.4796(3) 0.3497(2) 0.84730(13) 0.0336(5) Uani 1 1 d . . . C36 C -0.0144(3) 0.1755(2) 0.77288(12) 0.0296(5) Uani 1 1 d . . . H36 H 0.0364 0.1995 0.7423 0.035 Uiso 1 1 calc R . . C39 C 0.1129(4) 0.1582(3) 0.53173(14) 0.0476(7) Uani 1 1 d . . . H39 H 0.1206 0.0812 0.4997 0.057 Uiso 1 1 calc R . . C40 C -0.3043(3) 0.0535(4) 0.83191(16) 0.0531(8) Uani 1 1 d . . . H40A H -0.3169 -0.0430 0.8151 0.080 Uiso 1 1 calc R . . H40B H -0.3803 0.0972 0.8093 0.080 Uiso 1 1 calc R . . H40C H -0.2999 0.0718 0.8806 0.080 Uiso 1 1 calc R . . C42 C 0.4539(3) 0.3497(3) 0.77730(13) 0.0344(5) Uani 1 1 d . . . H42 H 0.3713 0.3241 0.7457 0.041 Uiso 1 1 calc R . . C43 C 0.8076(3) 0.4723(4) 0.84277(19) 0.0561(8) Uani 1 1 d . . . H43A H 0.8118 0.5680 0.8418 0.084 Uiso 1 1 calc R . . H43B H 0.8559 0.4256 0.8099 0.084 Uiso 1 1 calc R . . H43C H 0.8494 0.4584 0.8880 0.084 Uiso 1 1 calc R . . C45 C 0.4178(3) 0.3271(4) 0.95833(15) 0.0503(8) Uani 1 1 d . . . H45 H 0.5063 0.3583 0.9824 0.060 Uiso 1 1 calc R . . C47 C 0.0459(4) 0.3827(3) 0.55920(14) 0.0486(7) Uani 1 1 d . . . H47 H 0.0070 0.4599 0.5460 0.058 Uiso 1 1 calc R . . C49 C 0.0565(4) 0.2713(3) 0.51122(15) 0.0566(9) Uani 1 1 d . . . H49 H 0.0256 0.2721 0.4647 0.068 Uiso 1 1 calc R . . C50 C 0.1903(3) 0.2478(4) 0.95592(14) 0.0487(7) Uani 1 1 d . . . H50 H 0.1221 0.2258 0.9784 0.058 Uiso 1 1 calc R . . C52 C 0.3171(4) -0.2880(3) 0.59943(18) 0.0562(8) Uani 1 1 d . . . H52A H 0.4143 -0.2981 0.6109 0.084 Uiso 1 1 calc R . . H52B H 0.2867 -0.3022 0.5503 0.084 Uiso 1 1 calc R . . H52C H 0.2694 -0.3539 0.6172 0.084 Uiso 1 1 calc R . . C55 C 0.3196(4) 0.2943(4) 0.99200(15) 0.0616(10) Uani 1 1 d . . . H55 H 0.3406 0.3036 1.0396 0.074 Uiso 1 1 calc R . . C3 C -0.0200(4) 0.8223(3) 0.72522(19) 0.0561(8) Uani 1 1 d . . . H20A H 0.0485 0.8913 0.7518 0.084 Uiso 1 1 calc R . . H3B H -0.1003 0.8265 0.7449 0.084 Uiso 1 1 calc R . . H3C H -0.0443 0.8371 0.6788 0.084 Uiso 1 1 calc R . . S1AA S 0.4318(2) -0.30615(15) 0.74898(9) 0.0528(4) Uani 0.56 1 d PDU A 1 C1AA C 0.3635(3) -0.1516(2) 0.75507(13) 0.0377(5) Uani 0.56 1 d PDU A 1 C2AA C 0.3659(5) -0.0940(5) 0.8185(3) 0.0498(9) Uani 0.56 1 d PDU A 1 H2AA H 0.3318 -0.0092 0.8301 0.060 Uiso 0.56 1 calc PR A 1 C3AA C 0.4237(7) -0.1695(6) 0.8676(3) 0.0510(6) Uani 0.56 1 d PDU A 1 H3AA H 0.4330 -0.1408 0.9147 0.061 Uiso 0.56 1 calc PR A 1 C4AA C 0.4645(8) -0.2893(6) 0.8383(3) 0.0510(6) Uani 0.56 1 d PDU A 1 H4AA H 0.5047 -0.3541 0.8625 0.061 Uiso 0.56 1 calc PR A 1 S1AB S 0.3663(2) -0.0571(2) 0.83707(11) 0.0509(5) Uani 0.44 1 d PDU A 2 C1AB C 0.3635(3) -0.1516(2) 0.75507(13) 0.0377(5) Uani 0.44 1 d PDU A 2 C2AB C 0.4243(7) -0.2721(6) 0.7624(4) 0.0498(9) Uani 0.44 1 d PDU A 2 H2AB H 0.4336 -0.3379 0.7251 0.060 Uiso 0.44 1 calc PR A 2 C3AB C 0.4706(10) -0.2863(8) 0.8304(4) 0.0510(6) Uani 0.44 1 d PDU A 2 H3AB H 0.5139 -0.3618 0.8432 0.061 Uiso 0.44 1 calc PR A 2 C4AB C 0.4457(8) -0.1793(8) 0.8753(3) 0.0510(6) Uani 0.44 1 d PDU A 2 H4AB H 0.4697 -0.1728 0.9228 0.061 Uiso 0.44 1 calc PR A 2 C24A C 0.3073(3) -0.0916(2) 0.69635(13) 0.0334(5) Uani 1 1 d U . . S1AC S -0.1883(2) 0.1249(3) 0.62283(9) 0.0691(5) Uani 0.68 1 d PDU B 1 C1AC C -0.2394(3) 0.0882(3) 0.69161(13) 0.0391(6) Uani 0.68 1 d PDU B 1 C2AC C -0.3699(10) 0.0250(6) 0.6738(6) 0.071(2) Uani 0.68 1 d PDU B 1 H2AC H -0.4182 -0.0038 0.7042 0.085 Uiso 0.68 1 calc PR B 1 C3AC C -0.4201(8) 0.0104(8) 0.6004(3) 0.0776(18) Uani 0.68 1 d PDU B 1 H3AC H -0.5067 -0.0299 0.5779 0.093 Uiso 0.68 1 calc PR B 1 C4AC C -0.3326(6) 0.0590(8) 0.5680(3) 0.0640(16) Uani 0.68 1 d PDU B 1 H4AC H -0.3494 0.0567 0.5208 0.077 Uiso 0.68 1 calc PR B 1 S1AD S -0.3782(6) -0.0191(6) 0.6695(3) 0.0791(13) Uani 0.32 1 d PDU B 2 C1AD C -0.2394(3) 0.0882(3) 0.69161(13) 0.0391(6) Uani 0.32 1 d PDU B 2 C2AD C -0.2048(13) 0.1272(14) 0.6348(6) 0.059(3) Uani 0.32 1 d PDU B 2 H2AD H -0.1305 0.1868 0.6356 0.071 Uiso 0.32 1 calc PR B 2 C3AD C -0.3020(13) 0.0609(17) 0.5737(4) 0.062(2) Uani 0.32 1 d PDU B 2 H3AD H -0.2969 0.0740 0.5298 0.074 Uiso 0.32 1 calc PR B 2 C4AD C -0.3985(12) -0.0198(13) 0.5853(4) 0.067(3) Uani 0.32 1 d PDU B 2 H4AD H -0.4680 -0.0700 0.5514 0.081 Uiso 0.32 1 calc PR B 2 C31C C -0.1480(3) 0.1229(2) 0.75791(12) 0.0305(5) Uani 1 1 d DU . . S1A S 0.17157(17) 0.59752(13) 0.91126(6) 0.0509(3) Uani 0.76 1 d PDU C 1 C1A C 0.0993(3) 0.6897(2) 0.85134(14) 0.0381(6) Uani 0.76 1 d PDU C 1 C2A C 0.0710(6) 0.8127(7) 0.8822(4) 0.0529(14) Uani 0.76 1 d PDU C 1 H2A H 0.0313 0.8782 0.8585 0.064 Uiso 0.76 1 calc PR C 1 C3A C 0.1086(8) 0.8321(7) 0.9560(3) 0.0589(14) Uani 0.76 1 d PDU C 1 H3A H 0.0957 0.9113 0.9854 0.071 Uiso 0.76 1 calc PR C 1 C4A C 0.1638(8) 0.7238(6) 0.9774(3) 0.0583(13) Uani 0.76 1 d PDU C 1 H4A H 0.1945 0.7183 1.0234 0.070 Uiso 0.76 1 calc PR C 1 S1AE S 0.0404(7) 0.8405(5) 0.8817(4) 0.0625(15) Uani 0.24 1 d PDU C 2 C1AE C 0.0993(3) 0.6897(2) 0.85134(14) 0.0381(6) Uani 0.24 1 d PDU C 2 C2AE C 0.1568(15) 0.6283(12) 0.9027(6) 0.055(3) Uani 0.24 1 d PDU C 2 H2AE H 0.1950 0.5444 0.8962 0.066 Uiso 0.24 1 calc PR C 2 C3AE C 0.153(3) 0.7067(18) 0.9692(4) 0.058(3) Uani 0.24 1 d PDU C 2 H3AE H 0.1882 0.6794 1.0106 0.069 Uiso 0.24 1 calc PR C 2 C4AE C 0.093(2) 0.8228(16) 0.9645(4) 0.051(3) Uani 0.24 1 d PDU C 2 H4AE H 0.0808 0.8864 1.0021 0.061 Uiso 0.24 1 calc PR C 2 C24 C 0.0840(3) 0.6294(3) 0.77959(13) 0.0339(5) Uani 1 1 d DU . . S1AF S 0.73843(15) 0.50983(18) 0.68885(8) 0.0697(4) Uani 0.78 1 d PDU D 1 C1AF C 0.6016(3) 0.4172(3) 0.69938(16) 0.0452(7) Uani 0.78 1 d PDU D 1 C2AF C 0.5174(8) 0.3718(7) 0.6392(4) 0.0633(16) Uani 0.78 1 d PDU D 1 H2AF H 0.4366 0.3188 0.6347 0.076 Uiso 0.78 1 calc PR D 1 C3AF C 0.5598(7) 0.4103(7) 0.5824(3) 0.0671(13) Uani 0.78 1 d PDU D 1 H3AF H 0.5110 0.3864 0.5371 0.080 Uiso 0.78 1 calc PR D 1 C4AF C 0.6784(7) 0.4847(7) 0.6019(3) 0.0692(14) Uani 0.78 1 d PDU D 1 H4AF H 0.7235 0.5192 0.5718 0.083 Uiso 0.78 1 calc PR D 1 S1AG S 0.4832(7) 0.3587(8) 0.6266(4) 0.0713(19) Uani 0.22 1 d PDU D 2 C1AG C 0.6016(3) 0.4172(3) 0.69938(16) 0.0452(7) Uani 0.22 1 d PDU D 2 C2AG C 0.7023(13) 0.4917(15) 0.6864(8) 0.067(3) Uani 0.22 1 d PDU D 2 H2AG H 0.7768 0.5325 0.7205 0.080 Uiso 0.22 1 calc PR D 2 C3AG C 0.687(2) 0.504(3) 0.6170(6) 0.069(3) Uani 0.22 1 d PDU D 2 H3AG H 0.7497 0.5533 0.6002 0.083 Uiso 0.22 1 calc PR D 2 C4AG C 0.573(2) 0.437(2) 0.5788(5) 0.065(3) Uani 0.22 1 d PDU D 2 H4AG H 0.5449 0.4332 0.5316 0.079 Uiso 0.22 1 calc PR D 2 C31 C 0.5748(3) 0.3950(3) 0.76448(14) 0.0373(6) Uani 1 1 d DU . . 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 N6 0.0285(11) 0.0317(10) 0.0281(10) 0.0078(8) 0.0069(8) 0.0002(8) N7 0.0494(14) 0.0322(11) 0.0391(12) 0.0031(9) 0.0150(10) 0.0032(10) N8 0.0298(11) 0.0271(10) 0.0296(10) 0.0042(8) 0.0047(8) 0.0013(8) N9 0.0423(13) 0.0294(11) 0.0478(13) 0.0121(9) 0.0134(10) 0.0078(9) C1 0.0319(13) 0.0303(12) 0.0309(12) 0.0068(9) 0.0075(10) 0.0028(10) N11 0.0368(12) 0.0421(12) 0.0320(11) 0.0057(9) 0.0103(9) -0.0047(10) N12 0.0264(12) 0.0398(12) 0.0559(14) 0.0064(10) 0.0084(10) -0.0016(9) N13 0.0435(13) 0.0344(11) 0.0421(12) 0.0154(9) 0.0106(10) 0.0057(10) N14 0.0294(11) 0.0424(12) 0.0358(11) 0.0031(9) 0.0110(9) -0.0049(9) N1 0.0450(14) 0.0299(11) 0.0445(12) 0.0010(9) 0.0177(10) 0.0039(9) N2 0.0288(12) 0.0411(12) 0.0476(13) 0.0055(10) 0.0051(10) -0.0011(9) C18 0.0293(13) 0.0281(11) 0.0321(12) 0.0051(9) 0.0102(10) 0.0016(9) C19 0.0342(14) 0.0346(13) 0.0317(12) 0.0112(10) 0.0089(10) 0.0018(10) C22 0.0298(13) 0.0310(12) 0.0358(13) 0.0044(10) 0.0028(10) 0.0026(10) C23 0.0332(13) 0.0345(13) 0.0318(12) 0.0061(10) 0.0087(10) -0.0004(10) C26 0.0321(13) 0.0288(12) 0.0365(13) 0.0100(10) 0.0100(10) 0.0043(10) C27 0.0322(13) 0.0309(12) 0.0348(12) 0.0035(10) 0.0109(10) 0.0005(10) C30 0.0311(13) 0.0303(12) 0.0371(13) 0.0122(10) 0.0093(10) 0.0035(10) C33 0.0324(13) 0.0285(12) 0.0349(12) 0.0041(9) 0.0096(10) 0.0023(10) C35 0.0280(13) 0.0295(12) 0.0413(13) 0.0050(10) 0.0046(10) 0.0011(10) C36 0.0273(12) 0.0307(12) 0.0317(12) 0.0051(9) 0.0094(9) 0.0013(9) C39 0.064(2) 0.0461(16) 0.0305(13) 0.0015(11) 0.0099(13) 0.0039(14) C40 0.0418(17) 0.069(2) 0.0513(17) 0.0073(15) 0.0220(14) -0.0136(15) C42 0.0276(13) 0.0330(13) 0.0405(13) 0.0046(10) 0.0049(10) -0.0006(10) C43 0.0281(15) 0.064(2) 0.073(2) 0.0074(17) 0.0107(14) -0.0080(14) C45 0.0370(16) 0.069(2) 0.0371(15) 0.0068(14) -0.0063(12) -0.0056(14) C47 0.068(2) 0.0460(16) 0.0346(14) 0.0175(12) 0.0067(13) 0.0104(14) C49 0.084(3) 0.0585(19) 0.0273(13) 0.0133(13) 0.0054(14) 0.0098(17) C50 0.0436(17) 0.071(2) 0.0326(14) 0.0138(13) 0.0080(12) -0.0046(15) C52 0.074(2) 0.0341(15) 0.063(2) -0.0014(14) 0.0300(18) 0.0119(15) C55 0.056(2) 0.097(3) 0.0267(14) 0.0120(15) -0.0021(13) -0.0054(19) C3 0.068(2) 0.0360(15) 0.072(2) 0.0200(15) 0.0207(18) 0.0186(15) S1AA 0.0627(9) 0.0328(7) 0.0571(9) 0.0066(6) -0.0017(7) 0.0190(6) C1AA 0.0343(12) 0.0311(11) 0.0487(13) 0.0092(10) 0.0095(10) 0.0016(10) C2AA 0.0501(15) 0.0398(16) 0.0577(16) 0.0113(14) 0.0048(14) 0.0072(14) C3AA 0.0532(12) 0.0422(9) 0.0558(11) 0.0167(9) 0.0003(9) 0.0087(9) C4AA 0.0532(12) 0.0422(9) 0.0558(11) 0.0167(9) 0.0003(9) 0.0087(9) S1AB 0.0551(11) 0.0490(11) 0.0546(12) 0.0194(9) 0.0158(9) 0.0111(9) C1AB 0.0343(12) 0.0311(11) 0.0487(13) 0.0092(10) 0.0095(10) 0.0016(10) C2AB 0.0501(15) 0.0398(16) 0.0577(16) 0.0113(14) 0.0048(14) 0.0072(14) C3AB 0.0532(12) 0.0422(9) 0.0558(11) 0.0167(9) 0.0003(9) 0.0087(9) C4AB 0.0532(12) 0.0422(9) 0.0558(11) 0.0167(9) 0.0003(9) 0.0087(9) C24A 0.0299(13) 0.0296(12) 0.0420(13) 0.0050(10) 0.0123(10) 0.0009(10) S1AC 0.0504(9) 0.1181(13) 0.0348(7) 0.0113(7) 0.0064(6) -0.0230(9) C1AC 0.0300(13) 0.0498(14) 0.0365(12) 0.0069(11) 0.0060(10) -0.0016(11) C2AC 0.061(3) 0.097(4) 0.047(3) 0.019(3) -0.005(3) -0.040(3) C3AC 0.047(3) 0.122(4) 0.053(3) 0.007(3) -0.004(2) -0.024(3) C4AC 0.039(3) 0.109(3) 0.039(2) 0.012(2) -0.003(2) 0.005(3) S1AD 0.059(2) 0.109(3) 0.0581(19) 0.020(2) -0.0102(15) -0.042(2) C1AD 0.0300(13) 0.0498(14) 0.0365(12) 0.0069(11) 0.0060(10) -0.0016(11) C2AD 0.045(4) 0.081(5) 0.046(5) 0.001(4) 0.007(4) -0.005(4) C3AD 0.042(4) 0.102(4) 0.039(4) 0.011(4) 0.005(3) 0.004(4) C4AD 0.045(4) 0.103(5) 0.043(4) -0.002(4) 0.000(4) -0.005(4) C31C 0.0286(13) 0.0292(12) 0.0348(12) 0.0047(9) 0.0100(10) 0.0026(9) S1A 0.0704(8) 0.0440(6) 0.0378(5) 0.0037(4) 0.0133(5) 0.0093(5) C1A 0.0374(14) 0.0335(12) 0.0460(14) 0.0048(11) 0.0176(11) 0.0002(10) C2A 0.062(3) 0.041(3) 0.058(2) -0.006(2) 0.028(2) 0.016(2) C3A 0.070(3) 0.054(2) 0.053(2) -0.009(2) 0.031(2) 0.002(2) C4A 0.066(3) 0.060(3) 0.047(2) -0.001(2) 0.018(2) -0.005(2) S1AE 0.072(3) 0.042(2) 0.077(3) -0.009(2) 0.038(2) 0.016(2) C1AE 0.0374(14) 0.0335(12) 0.0460(14) 0.0048(11) 0.0176(11) 0.0002(10) C2AE 0.060(4) 0.048(4) 0.055(4) -0.001(4) 0.019(4) 0.000(4) C3AE 0.065(4) 0.054(4) 0.052(4) 0.002(4) 0.017(4) -0.003(4) C4AE 0.061(5) 0.053(4) 0.044(4) 0.001(4) 0.031(4) 0.001(4) C24 0.0320(13) 0.0304(12) 0.0421(13) 0.0090(10) 0.0124(11) 0.0013(10) S1AF 0.0522(8) 0.0876(9) 0.0766(8) 0.0232(7) 0.0266(6) -0.0176(7) C1AF 0.0385(15) 0.0466(15) 0.0563(16) 0.0136(13) 0.0198(12) 0.0039(12) C2AF 0.056(3) 0.078(3) 0.059(3) 0.016(3) 0.016(2) -0.004(3) C3AF 0.065(3) 0.083(3) 0.060(2) 0.023(2) 0.022(2) 0.001(2) C4AF 0.069(3) 0.086(3) 0.063(3) 0.022(3) 0.033(2) -0.001(2) S1AG 0.067(4) 0.097(4) 0.052(3) 0.015(2) 0.018(3) -0.008(3) C1AG 0.0385(15) 0.0466(15) 0.0563(16) 0.0136(13) 0.0198(12) 0.0039(12) C2AG 0.058(5) 0.077(4) 0.068(4) 0.015(4) 0.024(4) -0.003(4) C3AG 0.061(4) 0.083(5) 0.069(5) 0.020(4) 0.024(4) -0.003(4) C4AG 0.065(5) 0.078(5) 0.062(5) 0.024(4) 0.024(4) 0.001(5) C31 0.0325(14) 0.0327(13) 0.0475(15) 0.0060(11) 0.0117(11) 0.0027(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N6 C23 1.346(3) . ? N6 C19 1.342(3) . ? N7 C27 1.347(3) . ? N7 N1 1.357(3) . ? N8 C1 1.341(3) . ? N8 C22 1.344(3) . ? N9 N13 1.356(3) . ? N9 C24 1.369(3) . ? N9 C3 1.458(4) . ? C1 C50 1.394(4) . ? C1 C18 1.468(3) . ? N11 C18 1.340(3) . ? N11 N14 1.357(3) . ? N12 N2 1.359(3) . ? N12 C31 1.367(4) . ? N12 C43 1.461(4) . ? N13 C30 1.342(3) . ? N14 C31C 1.361(3) . ? N14 C40 1.459(4) . ? N1 C24A 1.365(3) . ? N1 C52 1.466(3) . ? N2 C35 1.340(3) . ? C18 C36 1.399(3) . ? C19 C47 1.394(4) . ? C19 C30 1.472(4) . ? C22 C45 1.397(4) . ? C22 C35 1.473(4) . ? C23 C39 1.394(4) . ? C23 C27 1.475(4) . ? C26 C24 1.385(3) . ? C26 C30 1.394(3) . ? C26 H26 0.9400 . ? C27 C33 1.398(3) . ? C33 C24A 1.386(3) . ? C33 H33 0.9400 . ? C35 C42 1.400(4) . ? C36 C31C 1.383(4) . ? C36 H36 0.9400 . ? C39 C49 1.383(5) . ? C39 H39 0.9400 . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C40 H40C 0.9700 . ? C42 C31 1.376(4) . ? C42 H42 0.9400 . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C43 H43C 0.9700 . ? C45 C55 1.376(5) . ? C45 H45 0.9400 . ? C47 C49 1.377(5) . ? C47 H47 0.9400 . ? C49 H49 0.9400 . ? C50 C55 1.380(5) . ? C50 H50 0.9400 . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C52 H52C 0.9700 . ? C55 H55 0.9400 . ? C3 H20A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? S1AA C1AA 1.717(3) . ? S1AA C4AA 1.764(6) . ? C1AA C2AA 1.318(6) . ? C1AA C24A 1.459(4) . ? C2AA C3AA 1.409(7) . ? C2AA H2AA 0.9400 . ? C3AA C4AA 1.364(7) . ? C3AA H3AA 0.9400 . ? C4AA H4AA 0.9400 . ? S1AB C4AB 1.708(6) . ? C2AB C3AB 1.408(8) . ? C2AB H2AB 0.9400 . ? C3AB C4AB 1.352(8) . ? C3AB H3AB 0.9400 . ? C4AB H4AB 0.9400 . ? S1AC C1AC 1.685(3) . ? S1AC C4AC 1.679(5) . ? C1AC C2AC 1.391(10) . ? C1AC C31C 1.453(4) . ? C2AC C3AC 1.460(12) . ? C2AC H2AC 0.9400 . ? C3AC C4AC 1.334(7) . ? C3AC H3AC 0.9400 . ? C4AC H4AC 0.9400 . ? S1AD C4AD 1.688(7) . ? C2AD C3AD 1.460(12) . ? C2AD H2AD 0.9400 . ? C3AD C4AD 1.333(8) . ? C3AD H3AD 0.9400 . ? C4AD H4AD 0.9400 . ? S1A C4A 1.701(5) . ? S1A C1A 1.725(3) . ? C1A C2A 1.355(7) . ? C1A C24 1.459(4) . ? C2A C3A 1.453(9) . ? C2A H2A 0.9400 . ? C3A C4A 1.342(6) . ? C3A H3A 0.9400 . ? C4A H4A 0.9400 . ? S1AE C4AE 1.708(6) . ? C2AE C3AE 1.455(10) . ? C2AE H2AE 0.9400 . ? C3AE C4AE 1.344(7) . ? C3AE H3AE 0.9400 . ? C4AE H4AE 0.9400 . ? S1AF C1AF 1.712(3) . ? S1AF C4AF 1.726(6) . ? C1AF C2AF 1.339(9) . ? C1AF C31 1.462(4) . ? C2AF C3AF 1.424(11) . ? C2AF H2AF 0.9400 . ? C3AF C4AF 1.339(6) . ? C3AF H3AF 0.9400 . ? C4AF H4AF 0.9400 . ? S1AG C4AG 1.728(8) . ? C2AG C3AG 1.424(12) . ? C2AG H2AG 0.9400 . ? C3AG C4AG 1.341(7) . ? C3AG H3AG 0.9400 . ? C4AG H4AG 0.9400 . ? 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 C23 N6 C19 118.2(2) . . ? C27 N7 N1 104.6(2) . . ? C1 N8 C22 118.5(2) . . ? N13 N9 C24 112.0(2) . . ? N13 N9 C3 118.5(2) . . ? C24 N9 C3 129.4(3) . . ? N8 C1 C50 122.6(2) . . ? N8 C1 C18 115.9(2) . . ? C50 C1 C18 121.5(2) . . ? C18 N11 N14 104.7(2) . . ? N2 N12 C31 112.3(2) . . ? N2 N12 C43 117.6(2) . . ? C31 N12 C43 130.1(3) . . ? C30 N13 N9 105.1(2) . . ? N11 N14 C31C 112.2(2) . . ? N11 N14 C40 118.1(2) . . ? C31C N14 C40 129.7(2) . . ? N7 N1 C24A 112.3(2) . . ? N7 N1 C52 118.1(2) . . ? C24A N1 C52 129.6(3) . . ? C35 N2 N12 104.4(2) . . ? N11 C18 C36 111.6(2) . . ? N11 C18 C1 120.9(2) . . ? C36 C18 C1 127.5(2) . . ? N6 C19 C47 122.5(2) . . ? N6 C19 C30 116.5(2) . . ? C47 C19 C30 121.0(2) . . ? N8 C22 C45 122.2(3) . . ? N8 C22 C35 115.4(2) . . ? C45 C22 C35 122.4(2) . . ? N6 C23 C39 122.7(2) . . ? N6 C23 C27 114.8(2) . . ? C39 C23 C27 122.4(2) . . ? C24 C26 C30 105.9(2) . . ? C24 C26 H26 127.1 . . ? C30 C26 H26 127.1 . . ? N7 C27 C33 111.5(2) . . ? N7 C27 C23 121.4(2) . . ? C33 C27 C23 127.1(2) . . ? N13 C30 C26 111.2(2) . . ? N13 C30 C19 120.7(2) . . ? C26 C30 C19 128.1(2) . . ? C24A C33 C27 105.4(2) . . ? C24A C33 H33 127.3 . . ? C27 C33 H33 127.3 . . ? N2 C35 C42 111.6(2) . . ? N2 C35 C22 120.8(2) . . ? C42 C35 C22 127.6(2) . . ? C31C C36 C18 105.2(2) . . ? C31C C36 H36 127.4 . . ? C18 C36 H36 127.4 . . ? C49 C39 C23 118.2(3) . . ? C49 C39 H39 120.9 . . ? C23 C39 H39 120.9 . . ? N14 C40 H40A 109.5 . . ? N14 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? N14 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C31 C42 C35 105.6(2) . . ? C31 C42 H42 127.2 . . ? C35 C42 H42 127.2 . . ? N12 C43 H43A 109.5 . . ? N12 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N12 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C55 C45 C22 118.4(3) . . ? C55 C45 H45 120.8 . . ? C22 C45 H45 120.8 . . ? C49 C47 C19 118.6(3) . . ? C49 C47 H47 120.7 . . ? C19 C47 H47 120.7 . . ? C47 C49 C39 119.8(3) . . ? C47 C49 H49 120.1 . . ? C39 C49 H49 120.1 . . ? C55 C50 C1 118.2(3) . . ? C55 C50 H50 120.9 . . ? C1 C50 H50 120.9 . . ? N1 C52 H52A 109.5 . . ? N1 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? N1 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C45 C55 C50 120.1(3) . . ? C45 C55 H55 119.9 . . ? C50 C55 H55 119.9 . . ? N9 C3 H20A 109.5 . . ? N9 C3 H3B 109.5 . . ? H20A C3 H3B 109.5 . . ? N9 C3 H3C 109.5 . . ? H20A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1AA S1AA C4AA 90.2(2) . . ? C2AA C1AA C24A 123.6(3) . . ? C2AA C1AA S1AA 112.7(3) . . ? C24A C1AA S1AA 123.7(2) . . ? C1AA C2AA C3AA 114.6(5) . . ? C1AA C2AA H2AA 122.7 . . ? C3AA C2AA H2AA 122.7 . . ? C4AA C3AA C2AA 111.8(5) . . ? C4AA C3AA H3AA 124.1 . . ? C2AA C3AA H3AA 124.1 . . ? C3AA C4AA S1AA 110.8(4) . . ? C3AA C4AA H4AA 124.6 . . ? S1AA C4AA H4AA 124.6 . . ? C3AB C2AB H2AB 122.9 . . ? C4AB C3AB C2AB 112.5(5) . . ? C4AB C3AB H3AB 123.8 . . ? C2AB C3AB H3AB 123.8 . . ? C3AB C4AB S1AB 113.2(5) . . ? C3AB C4AB H4AB 123.4 . . ? S1AB C4AB H4AB 123.4 . . ? N1 C24A C33 106.3(2) . . ? N1 C24A C1AA 126.5(2) . . ? C33 C24A C1AA 127.3(2) . . ? C1AC S1AC C4AC 94.5(3) . . ? C2AC C1AC C31C 129.6(5) . . ? C2AC C1AC S1AC 111.1(5) . . ? C31C C1AC S1AC 119.3(2) . . ? C1AC C2AC C3AC 109.3(8) . . ? C1AC C2AC H2AC 125.3 . . ? C3AC C2AC H2AC 125.3 . . ? C4AC C3AC C2AC 114.2(7) . . ? C4AC C3AC H3AC 122.9 . . ? C2AC C3AC H3AC 122.9 . . ? C3AC C4AC S1AC 110.9(6) . . ? C3AC C4AC H4AC 124.6 . . ? S1AC C4AC H4AC 124.6 . . ? C3AD C2AD H2AD 125.4 . . ? C4AD C3AD C2AD 114.5(8) . . ? C4AD C3AD H3AD 122.8 . . ? C2AD C3AD H3AD 122.7 . . ? C3AD C4AD S1AD 110.4(7) . . ? C3AD C4AD H4AD 124.8 . . ? S1AD C4AD H4AD 124.8 . . ? N14 C31C C36 106.4(2) . . ? N14 C31C C1AC 125.6(2) . . ? C36 C31C C1AC 127.9(2) . . ? C4A S1A C1A 92.8(2) . . ? C2A C1A C24 131.5(4) . . ? C2A C1A S1A 110.3(4) . . ? C24 C1A S1A 118.10(18) . . ? C1A C2A C3A 112.7(6) . . ? C1A C2A H2A 123.7 . . ? C3A C2A H2A 123.7 . . ? C4A C3A C2A 112.1(6) . . ? C4A C3A H3A 123.9 . . ? C2A C3A H3A 123.9 . . ? C3A C4A S1A 112.0(5) . . ? C3A C4A H4A 124.0 . . ? S1A C4A H4A 124.0 . . ? C3AE C2AE H2AE 123.8 . . ? C4AE C3AE C2AE 112.0(6) . . ? C4AE C3AE H3AE 124.0 . . ? C2AE C3AE H3AE 124.0 . . ? C3AE C4AE S1AE 111.7(6) . . ? C3AE C4AE H4AE 124.2 . . ? S1AE C4AE H4AE 124.2 . . ? N9 C24 C26 105.9(2) . . ? N9 C24 C1A 125.9(2) . . ? C26 C24 C1A 128.2(2) . . ? C1AF S1AF C4AF 91.9(2) . . ? C2AF C1AF C31 123.9(5) . . ? C2AF C1AF S1AF 110.3(5) . . ? C31 C1AF S1AF 125.7(2) . . ? C1AF C2AF C3AF 114.8(7) . . ? C1AF C2AF H2AF 122.6 . . ? C3AF C2AF H2AF 122.6 . . ? C4AF C3AF C2AF 111.2(6) . . ? C4AF C3AF H3AF 124.4 . . ? C2AF C3AF H3AF 124.4 . . ? C3AF C4AF S1AF 111.9(5) . . ? C3AF C4AF H4AF 124.0 . . ? S1AF C4AF H4AF 124.0 . . ? C3AG C2AG H2AG 122.6 . . ? C4AG C3AG C2AG 111.1(7) . . ? C4AG C3AG H3AG 124.5 . . ? C2AG C3AG H3AG 124.5 . . ? C3AG C4AG S1AG 111.8(6) . . ? C3AG C4AG H4AG 124.1 . . ? S1AG C4AG H4AG 124.1 . . ? C42 C31 N12 106.1(2) . . ? C42 C31 C1AF 127.5(3) . . ? N12 C31 C1AF 126.3(3) . . ? 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 N8 C1 C50 0.5(4) . . . . ? C22 N8 C1 C18 179.7(2) . . . . ? C24 N9 N13 C30 -0.2(3) . . . . ? C3 N9 N13 C30 -177.9(3) . . . . ? C18 N11 N14 C31C 0.2(3) . . . . ? C18 N11 N14 C40 -179.9(3) . . . . ? C27 N7 N1 C24A 0.1(3) . . . . ? C27 N7 N1 C52 179.4(3) . . . . ? C31 N12 N2 C35 0.3(3) . . . . ? C43 N12 N2 C35 178.7(3) . . . . ? N14 N11 C18 C36 0.1(3) . . . . ? N14 N11 C18 C1 -179.7(2) . . . . ? N8 C1 C18 N11 176.1(2) . . . . ? C50 C1 C18 N11 -4.8(4) . . . . ? N8 C1 C18 C36 -3.8(4) . . . . ? C50 C1 C18 C36 175.4(3) . . . . ? C23 N6 C19 C47 0.0(4) . . . . ? C23 N6 C19 C30 178.3(2) . . . . ? C1 N8 C22 C45 0.4(4) . . . . ? C1 N8 C22 C35 -178.4(2) . . . . ? C19 N6 C23 C39 0.5(4) . . . . ? C19 N6 C23 C27 -178.5(2) . . . . ? N1 N7 C27 C33 -0.1(3) . . . . ? N1 N7 C27 C23 -179.9(2) . . . . ? N6 C23 C27 N7 -179.4(2) . . . . ? C39 C23 C27 N7 1.5(4) . . . . ? N6 C23 C27 C33 0.8(4) . . . . ? C39 C23 C27 C33 -178.3(3) . . . . ? N9 N13 C30 C26 -0.1(3) . . . . ? N9 N13 C30 C19 178.5(2) . . . . ? C24 C26 C30 N13 0.3(3) . . . . ? C24 C26 C30 C19 -178.1(3) . . . . ? N6 C19 C30 N13 178.2(2) . . . . ? C47 C19 C30 N13 -3.4(4) . . . . ? N6 C19 C30 C26 -3.5(4) . . . . ? C47 C19 C30 C26 174.9(3) . . . . ? N7 C27 C33 C24A 0.0(3) . . . . ? C23 C27 C33 C24A 179.9(3) . . . . ? N12 N2 C35 C42 -0.3(3) . . . . ? N12 N2 C35 C22 -178.7(2) . . . . ? N8 C22 C35 N2 -177.9(2) . . . . ? C45 C22 C35 N2 3.3(4) . . . . ? N8 C22 C35 C42 4.0(4) . . . . ? C45 C22 C35 C42 -174.8(3) . . . . ? N11 C18 C36 C31C -0.4(3) . . . . ? C1 C18 C36 C31C 179.5(2) . . . . ? N6 C23 C39 C49 -0.4(5) . . . . ? C27 C23 C39 C49 178.6(3) . . . . ? N2 C35 C42 C31 0.3(3) . . . . ? C22 C35 C42 C31 178.5(2) . . . . ? N8 C22 C45 C55 -0.9(5) . . . . ? C35 C22 C45 C55 177.8(3) . . . . ? N6 C19 C47 C49 -0.6(5) . . . . ? C30 C19 C47 C49 -178.8(3) . . . . ? C19 C47 C49 C39 0.7(5) . . . . ? C23 C39 C49 C47 -0.2(5) . . . . ? N8 C1 C50 C55 -1.0(5) . . . . ? C18 C1 C50 C55 179.9(3) . . . . ? C22 C45 C55 C50 0.4(6) . . . . ? C1 C50 C55 C45 0.5(6) . . . . ? C4AA S1AA C1AA C2AA 0.07(15) . . . . ? C4AA S1AA C1AA C24A -179.1(3) . . . . ? C24A C1AA C2AA C3AA 179.5(3) . . . . ? S1AA C1AA C2AA C3AA 0.3(2) . . . . ? C1AA C2AA C3AA C4AA -0.6(4) . . . . ? C2AA C3AA C4AA S1AA 0.6(4) . . . . ? C1AA S1AA C4AA C3AA -0.4(3) . . . . ? C2AB C3AB C4AB S1AB -0.3(4) . . . . ? N7 N1 C24A C33 0.0(3) . . . . ? C52 N1 C24A C33 -179.3(3) . . . . ? N7 N1 C24A C1AA 179.4(2) . . . . ? C52 N1 C24A C1AA 0.2(5) . . . . ? C27 C33 C24A N1 0.0(3) . . . . ? C27 C33 C24A C1AA -179.4(2) . . . . ? C2AA C1AA C24A N1 -172.3(3) . . . . ? S1AA C1AA C24A N1 6.8(4) . . . . ? C2AA C1AA C24A C33 7.1(4) . . . . ? S1AA C1AA C24A C33 -173.8(2) . . . . ? C4AC S1AC C1AC C2AC -0.45(15) . . . . ? C4AC S1AC C1AC C31C 179.0(3) . . . . ? C31C C1AC C2AC C3AC -179.1(4) . . . . ? S1AC C1AC C2AC C3AC 0.27(19) . . . . ? C1AC C2AC C3AC C4AC 0.1(4) . . . . ? C2AC C3AC C4AC S1AC -0.4(5) . . . . ? C1AC S1AC C4AC C3AC 0.5(3) . . . . ? C2AD C3AD C4AD S1AD 0.4(5) . . . . ? N11 N14 C31C C36 -0.4(3) . . . . ? C40 N14 C31C C36 179.7(3) . . . . ? N11 N14 C31C C1AC 177.9(2) . . . . ? C40 N14 C31C C1AC -2.0(5) . . . . ? C18 C36 C31C N14 0.5(3) . . . . ? C18 C36 C31C C1AC -177.8(2) . . . . ? C2AC C1AC C31C N14 -3.9(4) . . . . ? S1AC C1AC C31C N14 176.7(2) . . . . ? C2AC C1AC C31C C36 174.0(3) . . . . ? S1AC C1AC C31C C36 -5.4(4) . . . . ? C4A S1A C1A C2A -0.08(14) . . . . ? C4A S1A C1A C24 177.6(3) . . . . ? C24 C1A C2A C3A -177.4(4) . . . . ? S1A C1A C2A C3A -0.07(19) . . . . ? C1A C2A C3A C4A 0.2(4) . . . . ? C2A C3A C4A S1A -0.3(4) . . . . ? C1A S1A C4A C3A 0.2(3) . . . . ? C2AE C3AE C4AE S1AE -0.1(5) . . . . ? N13 N9 C24 C26 0.4(3) . . . . ? C3 N9 C24 C26 177.7(3) . . . . ? N13 N9 C24 C1A 179.9(2) . . . . ? C3 N9 C24 C1A -2.8(5) . . . . ? C30 C26 C24 N9 -0.4(3) . . . . ? C30 C26 C24 C1A -179.9(3) . . . . ? C2A C1A C24 N9 -0.2(4) . . . . ? S1A C1A C24 N9 -177.3(2) . . . . ? C2A C1A C24 C26 179.3(3) . . . . ? S1A C1A C24 C26 2.1(4) . . . . ? C4AF S1AF C1AF C2AF -0.13(15) . . . . ? C4AF S1AF C1AF C31 -177.3(4) . . . . ? C31 C1AF C2AF C3AF 177.1(4) . . . . ? S1AF C1AF C2AF C3AF -0.1(2) . . . . ? C1AF C2AF C3AF C4AF 0.4(4) . . . . ? C2AF C3AF C4AF S1AF -0.5(4) . . . . ? C1AF S1AF C4AF C3AF 0.4(3) . . . . ? C2AG C3AG C4AG S1AG 0.0(5) . . . . ? C35 C42 C31 N12 -0.1(3) . . . . ? C35 C42 C31 C1AF -178.1(3) . . . . ? N2 N12 C31 C42 -0.1(3) . . . . ? C43 N12 C31 C42 -178.3(3) . . . . ? N2 N12 C31 C1AF 178.0(2) . . . . ? C43 N12 C31 C1AF -0.2(5) . . . . ? C2AF C1AF C31 C42 -13.4(4) . . . . ? S1AF C1AF C31 C42 163.4(3) . . . . ? C2AF C1AF C31 N12 168.9(3) . . . . ? S1AF C1AF C31 N12 -14.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.509 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.061