# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jason Clyburne' 'Dharinee D. Choytun' 'Jason A. C. Clyburne' 'Thomas P. Johansson' 'Lisa D. Langlois' 'Gary W. Leach' 'Charles L. B. Macdonald' 'Noham Weinberg' _publ_contact_author_name 'Dr Jason Clyburne' _publ_contact_author_address ; Department of Chemistry Simon Fraser University Burnaby BC V5A1S6 CANADA ; _publ_contact_author_email CLYBURNE@SFU.CA _publ_requested_journal 'Chemical Communications' _publ_section_title ; Azines Possessing Strong Push/Pull Donors/Acceptors ; data_cmjc61 _database_code_depnum_ccdc_archive 'CCDC 236035' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H30 Cl2 N4' _chemical_formula_weight 565.52 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 10.5020(5) _cell_length_b 11.0120(5) _cell_length_c 25.2110(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2915.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8333 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.253 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 11349 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 20.00 _reflns_number_total 2700 _reflns_number_gt 2246 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0353P)^2^+0.6365P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.24(12) _refine_ls_number_reflns 2700 _refine_ls_number_parameters 495 _refine_ls_number_restraints 2030 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 0.827 _refine_ls_shift/su_max 0.357 _refine_ls_shift/su_mean 0.046 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 N11 N 1.2640(5) 1.0500(5) 0.3408(2) 0.0287(11) Uani 0.6564(17) 1 d PDU A 1 N12 N 1.2054(5) 1.0105(5) 0.29605(19) 0.0282(9) Uani 0.6564(17) 1 d PDU A 1 C100 C 1.3608(9) 1.1260(9) 0.3309(3) 0.0269(15) Uani 0.6564(17) 1 d PDU A 1 N13 N 1.4111(8) 1.1762(9) 0.2852(3) 0.0334(16) Uani 0.6564(17) 1 d PDU A 1 C101 C 1.5079(11) 1.2576(10) 0.3012(3) 0.033(2) Uani 0.6564(17) 1 d PDU A 1 H101 H 1.5589 1.3037 0.2787 0.040 Uiso 0.6564(17) 1 calc PR A 1 C102 C 1.5130(10) 1.2568(10) 0.3539(3) 0.031(2) Uani 0.6564(17) 1 d PDU A 1 H102 H 1.5695 1.3005 0.3749 0.038 Uiso 0.6564(17) 1 calc PR A 1 N14 N 1.4199(9) 1.1798(9) 0.3715(3) 0.0325(17) Uani 0.6564(17) 1 d PDU A 1 C111 C 1.1025(6) 0.9452(7) 0.3047(2) 0.0259(10) Uani 0.6564(17) 1 d PDU A 1 C112 C 1.0265(6) 0.9055(7) 0.2610(2) 0.0271(13) Uani 0.6564(17) 1 d PDU A 1 C113 C 1.0475(7) 0.9041(7) 0.2068(2) 0.0351(15) Uani 0.6564(17) 1 d PDU A 1 H113 H 1.1214 0.9368 0.1923 0.042 Uiso 0.6564(17) 1 calc PR A 1 C114 C 0.9561(6) 0.8532(7) 0.1749(2) 0.0344(14) Uani 0.6564(17) 1 d PDU A 1 Cl11 Cl 0.9876(2) 0.8430(2) 0.10712(8) 0.0611(5) Uani 0.6564(17) 1 d PDU A 1 C115 C 0.8433(8) 0.8060(9) 0.1942(3) 0.0457(18) Uani 0.6564(17) 1 d PDU A 1 H115 H 0.7836 0.7735 0.1709 0.055 Uiso 0.6564(17) 1 calc PR A 1 C116 C 0.8193(8) 0.8071(11) 0.2485(3) 0.0377(17) Uani 0.6564(17) 1 d PDU A 1 H116 H 0.7423 0.7791 0.2620 0.045 Uiso 0.6564(17) 1 calc PR A 1 C117 C 0.9152(6) 0.8519(8) 0.2825(2) 0.0301(14) Uani 0.6564(17) 1 d PDU A 1 C118 C 0.9206(6) 0.8565(8) 0.3396(2) 0.0264(14) Uani 0.6564(17) 1 d PDU A 1 C119 C 0.8406(8) 0.8178(9) 0.3781(2) 0.0332(15) Uani 0.6564(17) 1 d PDU A 1 H119 H 0.7612 0.7875 0.3686 0.040 Uiso 0.6564(17) 1 calc PR A 1 C120 C 0.8733(7) 0.8218(8) 0.4310(3) 0.0349(15) Uani 0.6564(17) 1 d PDU A 1 H120 H 0.8196 0.7893 0.4567 0.042 Uiso 0.6564(17) 1 calc PR A 1 C121 C 0.9894(7) 0.8759(8) 0.4453(2) 0.0436(17) Uani 0.6564(17) 1 d PDU A 1 Cl12 Cl 1.0341(2) 0.8731(2) 0.51208(8) 0.0685(6) Uani 0.6564(17) 1 d PDU A 1 C122 C 1.0725(7) 0.9171(7) 0.4080(3) 0.0358(15) Uani 0.6564(17) 1 d PDU A 1 H122 H 1.1505 0.9497 0.4180 0.043 Uiso 0.6564(17) 1 calc PR A 1 C123 C 1.0389(6) 0.9098(7) 0.3543(2) 0.0261(12) Uani 0.6564(17) 1 d PDU A 1 C131 C 1.3808(12) 1.1458(11) 0.2313(3) 0.0305(19) Uani 0.6564(17) 1 d PDU A 1 C132 C 1.4287(19) 1.0360(14) 0.2133(4) 0.039(2) Uani 0.6564(17) 1 d PDU A 1 C133 C 1.3928(12) 1.0002(13) 0.1621(4) 0.041(2) Uani 0.6564(17) 1 d PDU A 1 H133 H 1.4177 0.9241 0.1500 0.049 Uiso 0.6564(17) 1 calc PR A 1 C134 C 1.3215(10) 1.0742(11) 0.1286(3) 0.041(2) Uani 0.6564(17) 1 d PDU A 1 C135 C 1.2865(12) 1.1834(10) 0.1493(3) 0.040(2) Uani 0.6564(17) 1 d PDU A 1 H134 H 1.2426 1.2364 0.1271 0.048 Uiso 0.6564(17) 1 calc PR A 1 C136 C 1.3104(9) 1.2213(10) 0.1994(3) 0.030(2) Uani 0.6564(17) 1 d PDU A 1 C137 C 1.504(2) 0.956(2) 0.2499(5) 0.044(3) Uani 0.6564(17) 1 d PDU A 1 H37A H 1.5334 0.8856 0.2308 0.066 Uiso 0.6564(17) 1 calc PR A 1 H37B H 1.4508 0.9299 0.2788 0.066 Uiso 0.6564(17) 1 calc PR A 1 H37C H 1.5756 0.9997 0.2635 0.066 Uiso 0.6564(17) 1 calc PR A 1 C138 C 1.2911(12) 1.0284(13) 0.0749(3) 0.060(2) Uani 0.6564(17) 1 d PDU A 1 H38A H 1.2790 1.0958 0.0513 0.090 Uiso 0.6564(17) 1 calc PR A 1 H38B H 1.2146 0.9808 0.0763 0.090 Uiso 0.6564(17) 1 calc PR A 1 H38C H 1.3600 0.9789 0.0624 0.090 Uiso 0.6564(17) 1 calc PR A 1 C139 C 1.270(2) 1.3479(14) 0.2179(5) 0.054(3) Uani 0.6564(17) 1 d PDU A 1 H39A H 1.2014 1.3766 0.1963 0.080 Uiso 0.6564(17) 1 calc PR A 1 H39B H 1.3412 1.4025 0.2149 0.080 Uiso 0.6564(17) 1 calc PR A 1 H39C H 1.2433 1.3441 0.2542 0.080 Uiso 0.6564(17) 1 calc PR A 1 C141 C 1.4013(16) 1.1400(12) 0.4249(3) 0.0325(17) Uani 0.6564(17) 1 d PDU A 1 C142 C 1.446(2) 1.0274(15) 0.4417(4) 0.038(2) Uani 0.6564(17) 1 d PDU A 1 C143 C 1.424(2) 0.9912(15) 0.4927(4) 0.044(2) Uani 0.6564(17) 1 d PDU A 1 H143 H 1.4593 0.9189 0.5046 0.052 Uiso 0.6564(17) 1 calc PR A 1 C144 C 1.350(2) 1.0586(16) 0.5268(5) 0.046(2) Uani 0.6564(17) 1 d PDU A 1 C145 C 1.3096(14) 1.1752(12) 0.5112(3) 0.039(2) Uani 0.6564(17) 1 d PDU A 1 H145 H 1.2691 1.2256 0.5355 0.047 Uiso 0.6564(17) 1 calc PR A 1 C146 C 1.330(2) 1.2153(15) 0.4587(4) 0.0342(19) Uani 0.6564(17) 1 d PDU A 1 C147 C 1.5335(10) 0.9526(11) 0.4070(4) 0.044(2) Uani 0.6564(17) 1 d PDU A 1 H47A H 1.5879 1.0057 0.3870 0.066 Uiso 0.6564(17) 1 calc PR A 1 H47B H 1.4836 0.9043 0.3831 0.066 Uiso 0.6564(17) 1 calc PR A 1 H47C H 1.5846 0.9004 0.4288 0.066 Uiso 0.6564(17) 1 calc PR A 1 C148 C 1.320(3) 1.0161(19) 0.5829(5) 0.072(3) Uani 0.6564(17) 1 d PDU A 1 H48A H 1.2321 0.9909 0.5845 0.108 Uiso 0.6564(17) 1 calc PR A 1 H48B H 1.3333 1.0816 0.6073 0.108 Uiso 0.6564(17) 1 calc PR A 1 H48C H 1.3736 0.9490 0.5920 0.108 Uiso 0.6564(17) 1 calc PR A 1 C149 C 1.2826(13) 1.3365(11) 0.4427(3) 0.037(2) Uani 0.6564(17) 1 d PDU A 1 H49A H 1.3533 1.3887 0.4348 0.056 Uiso 0.6564(17) 1 calc PR A 1 H49B H 1.2337 1.3709 0.4712 0.056 Uiso 0.6564(17) 1 calc PR A 1 H49C H 1.2298 1.3286 0.4118 0.056 Uiso 0.6564(17) 1 calc PR A 1 N21 N 1.2691(10) 1.0509(11) 0.3033(4) 0.0287(11) Uani 0.3436(17) 1 d PDU A 2 N22 N 1.2066(9) 1.0118(11) 0.3476(4) 0.0282(9) Uani 0.3436(17) 1 d PDU A 2 C200 C 1.358(2) 1.138(2) 0.3112(5) 0.0269(15) Uani 0.3436(17) 1 d PDU A 2 N23 N 1.4188(19) 1.1817(18) 0.3560(6) 0.0334(16) Uani 0.3436(17) 1 d PDU A 2 C201 C 1.504(2) 1.2731(19) 0.3375(7) 0.033(2) Uani 0.3436(17) 1 d PDU A 2 H201 H 1.5514 1.3249 0.3588 0.040 Uiso 0.3436(17) 1 calc PR A 2 C202 C 1.504(2) 1.272(2) 0.2848(7) 0.031(2) Uani 0.3436(17) 1 d PDU A 2 H202 H 1.5505 1.3226 0.2626 0.038 Uiso 0.3436(17) 1 calc PR A 2 N24 N 1.4207(18) 1.1826(16) 0.2696(6) 0.0325(17) Uani 0.3436(17) 1 d PDU A 2 C211 C 1.1033(11) 0.9479(14) 0.3402(4) 0.0259(10) Uani 0.3436(17) 1 d PDU A 2 C212 C 1.0327(13) 0.9028(16) 0.3849(4) 0.0261(12) Uani 0.3436(17) 1 d PDU A 2 C213 C 1.0578(13) 0.9023(15) 0.4401(4) 0.0358(15) Uani 0.3436(17) 1 d PDU A 2 H21A H 1.1322 0.9361 0.4537 0.043 Uiso 0.3436(17) 1 calc PR A 2 C214 C 0.9671(13) 0.8493(17) 0.4737(4) 0.0436(17) Uani 0.3436(17) 1 d PDU A 2 Cl21 Cl 1.0003(5) 0.8388(6) 0.54196(17) 0.0685(6) Uani 0.3436(17) 1 d PDU A 2 C215 C 0.8531(13) 0.7992(17) 0.4555(4) 0.0349(15) Uani 0.3436(17) 1 d PDU A 2 H21B H 0.7948 0.7664 0.4792 0.042 Uiso 0.3436(17) 1 calc PR A 2 C216 C 0.8276(17) 0.799(2) 0.4004(5) 0.0332(15) Uani 0.3436(17) 1 d PDU A 2 H21C H 0.7520 0.7671 0.3873 0.040 Uiso 0.3436(17) 1 calc PR A 2 C217 C 0.9201(14) 0.8487(18) 0.3658(4) 0.0264(14) Uani 0.3436(17) 1 d PDU A 2 C218 C 0.9131(13) 0.863(2) 0.3087(4) 0.0301(14) Uani 0.3436(17) 1 d PDU A 2 C219 C 0.8419(17) 0.815(2) 0.2695(5) 0.0377(17) Uani 0.3436(17) 1 d PDU A 2 H21D H 0.7733 0.7666 0.2796 0.045 Uiso 0.3436(17) 1 calc PR A 2 C220 C 0.8616(16) 0.830(2) 0.2160(5) 0.0457(18) Uani 0.3436(17) 1 d PDU A 2 H22A H 0.7990 0.8157 0.1907 0.055 Uiso 0.3436(17) 1 calc PR A 2 C221 C 0.9854(13) 0.8691(16) 0.2032(4) 0.0344(14) Uani 0.3436(17) 1 d PDU A 2 Cl22 Cl 1.0224(4) 0.8799(4) 0.13669(17) 0.0611(5) Uani 0.3436(17) 1 d PDU A 2 C222 C 1.0640(14) 0.9237(16) 0.2391(4) 0.0351(15) Uani 0.3436(17) 1 d PDU A 2 H22B H 1.1333 0.9702 0.2285 0.042 Uiso 0.3436(17) 1 calc PR A 2 C223 C 1.0351(11) 0.9064(14) 0.2930(4) 0.0271(13) Uani 0.3436(17) 1 d PDU A 2 C231 C 1.397(3) 1.148(2) 0.4106(7) 0.0325(17) Uani 0.3436(17) 1 d PDU A 2 C232 C 1.444(5) 1.034(3) 0.4264(9) 0.038(2) Uani 0.3436(17) 1 d PDU A 2 C233 C 1.411(4) 1.002(3) 0.4785(9) 0.044(2) Uani 0.3436(17) 1 d PDU A 2 H233 H 1.4331 0.9244 0.4901 0.052 Uiso 0.3436(17) 1 calc PR A 2 C234 C 1.346(5) 1.076(3) 0.5139(11) 0.046(2) Uani 0.3436(17) 1 d PDU A 2 C235 C 1.302(3) 1.184(2) 0.4933(7) 0.039(2) Uani 0.3436(17) 1 d PDU A 2 H235 H 1.2509 1.2326 0.5146 0.047 Uiso 0.3436(17) 1 calc PR A 2 C236 C 1.330(5) 1.224(3) 0.4442(9) 0.0342(19) Uani 0.3436(17) 1 d PDU A 2 C237 C 1.504(2) 0.951(2) 0.3863(7) 0.044(2) Uani 0.3436(17) 1 d PDU A 2 H37D H 1.5474 0.8861 0.4043 0.066 Uiso 0.3436(17) 1 calc PR A 2 H37E H 1.5632 0.9952 0.3649 0.066 Uiso 0.3436(17) 1 calc PR A 2 H37F H 1.4384 0.9170 0.3640 0.066 Uiso 0.3436(17) 1 calc PR A 2 C238 C 1.314(6) 1.033(4) 0.5681(11) 0.072(3) Uani 0.3436(17) 1 d PDU A 2 H39D H 1.2239 1.0382 0.5734 0.108 Uiso 0.3436(17) 1 calc PR A 2 H38E H 1.3567 1.0833 0.5938 0.108 Uiso 0.3436(17) 1 calc PR A 2 H38F H 1.3414 0.9505 0.5723 0.108 Uiso 0.3436(17) 1 calc PR A 2 C239 C 1.280(3) 1.345(2) 0.4223(7) 0.037(2) Uani 0.3436(17) 1 d PDU A 2 H39D' H 1.2107 1.3729 0.4439 0.056 Uiso 0.3436(17) 1 calc PR A 2 H39E H 1.2510 1.3336 0.3865 0.056 Uiso 0.3436(17) 1 calc PR A 2 H39F H 1.3473 1.4038 0.4228 0.056 Uiso 0.3436(17) 1 calc PR A 2 C241 C 1.401(2) 1.143(2) 0.2161(6) 0.0305(19) Uani 0.3436(17) 1 d PDU A 2 C242 C 1.441(4) 1.029(3) 0.1981(8) 0.039(2) Uani 0.3436(17) 1 d PDU A 2 C243 C 1.417(3) 0.995(2) 0.1474(7) 0.041(2) Uani 0.3436(17) 1 d PDU A 2 H243 H 1.4454 0.9194 0.1357 0.049 Uiso 0.3436(17) 1 calc PR A 2 C244 C 1.350(2) 1.068(2) 0.1133(7) 0.041(2) Uani 0.3436(17) 1 d PDU A 2 C245 C 1.302(3) 1.180(2) 0.1308(6) 0.040(2) Uani 0.3436(17) 1 d PDU A 2 H245 H 1.2487 1.2257 0.1090 0.048 Uiso 0.3436(17) 1 calc PR A 2 C246 C 1.335(2) 1.2221(18) 0.1821(6) 0.030(2) Uani 0.3436(17) 1 d PDU A 2 C247 C 1.515(4) 0.947(4) 0.2348(12) 0.044(3) Uani 0.3436(17) 1 d PDU A 2 H47D H 1.5471 0.8789 0.2153 0.066 Uiso 0.3436(17) 1 calc PR A 2 H47E H 1.4604 0.9192 0.2627 0.066 Uiso 0.3436(17) 1 calc PR A 2 H47F H 1.5852 0.9915 0.2499 0.066 Uiso 0.3436(17) 1 calc PR A 2 C248 C 1.313(3) 1.027(3) 0.0572(6) 0.060(2) Uani 0.3436(17) 1 d PDU A 2 H48D H 1.2216 1.0217 0.0548 0.090 Uiso 0.3436(17) 1 calc PR A 2 H48E H 1.3493 0.9488 0.0500 0.090 Uiso 0.3436(17) 1 calc PR A 2 H48F H 1.3434 1.0849 0.0318 0.090 Uiso 0.3436(17) 1 calc PR A 2 C249 C 1.283(5) 1.340(3) 0.2023(12) 0.054(3) Uani 0.3436(17) 1 d PDU A 2 H49D H 1.3229 1.4062 0.1837 0.080 Uiso 0.3436(17) 1 calc PR A 2 H49E H 1.3005 1.3472 0.2395 0.080 Uiso 0.3436(17) 1 calc PR A 2 H49F H 1.1929 1.3427 0.1965 0.080 Uiso 0.3436(17) 1 calc PR A 2 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 N11 0.014(2) 0.022(2) 0.050(3) -0.005(3) -0.003(3) -0.0034(16) N12 0.014(3) 0.025(2) 0.045(2) -0.004(3) -0.003(3) -0.0026(17) C100 0.021(2) 0.016(3) 0.043(4) 0.009(4) -0.006(4) 0.0024(19) N13 0.026(3) 0.026(3) 0.047(4) 0.001(3) 0.006(3) -0.005(2) C101 0.036(4) 0.015(4) 0.048(5) 0.013(5) 0.000(5) -0.009(3) C102 0.027(3) 0.018(4) 0.049(5) 0.018(4) -0.014(4) -0.007(3) N14 0.032(3) 0.024(3) 0.042(4) -0.003(3) 0.009(3) -0.007(2) C111 0.011(2) 0.014(2) 0.053(3) -0.006(4) 0.006(3) -0.0018(16) C112 0.018(2) 0.021(3) 0.043(3) 0.009(4) -0.006(3) 0.005(2) C113 0.044(4) 0.010(4) 0.050(3) 0.003(4) 0.006(3) -0.014(3) C114 0.039(4) 0.013(3) 0.051(3) 0.003(4) -0.009(3) -0.001(3) Cl11 0.0673(13) 0.0613(13) 0.0546(13) -0.0032(11) -0.0053(10) -0.0155(10) C115 0.042(3) 0.031(5) 0.065(4) -0.006(5) -0.010(4) -0.012(3) C116 0.017(3) 0.034(4) 0.062(4) 0.010(5) -0.012(4) 0.009(3) C117 0.026(3) 0.015(3) 0.050(3) 0.001(4) -0.001(3) -0.004(2) C118 0.015(2) 0.016(3) 0.048(4) 0.025(5) -0.003(4) 0.001(2) C119 0.025(3) 0.018(4) 0.057(4) 0.010(5) 0.006(4) -0.012(3) C120 0.030(3) 0.027(4) 0.047(4) 0.009(4) 0.023(3) 0.005(3) C121 0.035(4) 0.045(5) 0.052(4) 0.002(4) 0.010(3) -0.008(3) Cl12 0.0636(13) 0.0897(16) 0.0521(15) -0.0041(13) 0.0068(11) -0.0089(11) C122 0.021(3) 0.032(4) 0.055(3) 0.008(5) -0.001(3) 0.007(3) C123 0.016(3) 0.014(3) 0.048(3) 0.002(4) -0.002(3) -0.002(2) C131 0.018(4) 0.027(3) 0.047(4) -0.007(4) 0.014(4) -0.002(3) C132 0.025(5) 0.037(3) 0.057(6) -0.009(4) 0.011(6) 0.004(2) C133 0.038(6) 0.037(3) 0.046(6) -0.015(4) 0.031(5) -0.005(3) C134 0.036(5) 0.058(4) 0.030(5) -0.008(4) 0.033(4) 0.000(3) C135 0.041(4) 0.043(3) 0.036(5) 0.005(4) 0.028(5) 0.000(3) C136 0.024(4) 0.026(3) 0.040(5) 0.002(4) 0.027(4) -0.005(3) C137 0.030(4) 0.020(4) 0.082(8) -0.012(7) 0.007(7) 0.001(3) C138 0.063(6) 0.092(5) 0.026(5) -0.007(5) 0.041(5) 0.000(4) C139 0.052(6) 0.035(4) 0.073(9) -0.012(4) 0.013(7) 0.009(3) C141 0.034(3) 0.023(3) 0.041(4) 0.004(3) 0.002(4) -0.001(2) C142 0.030(3) 0.017(3) 0.068(7) 0.012(5) -0.010(8) -0.006(3) C143 0.033(5) 0.038(4) 0.060(6) 0.015(4) -0.025(6) 0.005(3) C144 0.041(3) 0.043(5) 0.053(6) 0.014(4) -0.019(6) -0.005(4) C145 0.042(3) 0.046(4) 0.028(5) -0.005(5) -0.011(6) 0.008(3) C146 0.039(3) 0.036(4) 0.027(6) 0.001(4) -0.008(7) -0.001(3) C147 0.026(5) 0.034(4) 0.072(7) 0.006(5) -0.021(4) 0.013(4) C148 0.084(4) 0.076(7) 0.055(8) 0.022(5) -0.011(9) -0.013(5) C149 0.054(3) 0.037(4) 0.021(7) -0.002(5) -0.005(6) 0.007(3) N21 0.014(2) 0.022(2) 0.050(3) -0.005(3) -0.003(3) -0.0034(16) N22 0.014(3) 0.025(2) 0.045(2) -0.004(3) -0.003(3) -0.0026(17) C200 0.021(2) 0.016(3) 0.043(4) 0.009(4) -0.006(4) 0.0024(19) N23 0.026(3) 0.026(3) 0.047(4) 0.001(3) 0.006(3) -0.005(2) C201 0.036(4) 0.015(4) 0.048(5) 0.013(5) 0.000(5) -0.009(3) C202 0.027(3) 0.018(4) 0.049(5) 0.018(4) -0.014(4) -0.007(3) N24 0.032(3) 0.024(3) 0.042(4) -0.003(3) 0.009(3) -0.007(2) C211 0.011(2) 0.014(2) 0.053(3) -0.006(4) 0.006(3) -0.0018(16) C212 0.016(3) 0.014(3) 0.048(3) 0.002(4) -0.002(3) -0.002(2) C213 0.021(3) 0.032(4) 0.055(3) 0.008(5) -0.001(3) 0.007(3) C214 0.035(4) 0.045(5) 0.052(4) 0.002(4) 0.010(3) -0.008(3) Cl21 0.0636(13) 0.0897(16) 0.0521(15) -0.0041(13) 0.0068(11) -0.0089(11) C215 0.030(3) 0.027(4) 0.047(4) 0.009(4) 0.023(3) 0.005(3) C216 0.025(3) 0.018(4) 0.057(4) 0.010(5) 0.006(4) -0.012(3) C217 0.015(2) 0.016(3) 0.048(4) 0.025(5) -0.003(4) 0.001(2) C218 0.026(3) 0.015(3) 0.050(3) 0.001(4) -0.001(3) -0.004(2) C219 0.017(3) 0.034(4) 0.062(4) 0.010(5) -0.012(4) 0.009(3) C220 0.042(3) 0.031(5) 0.065(4) -0.006(5) -0.010(4) -0.012(3) C221 0.039(4) 0.013(3) 0.051(3) 0.003(4) -0.009(3) -0.001(3) Cl22 0.0673(13) 0.0613(13) 0.0546(13) -0.0032(11) -0.0053(10) -0.0155(10) C222 0.044(4) 0.010(4) 0.050(3) 0.003(4) 0.006(3) -0.014(3) C223 0.018(2) 0.021(3) 0.043(3) 0.009(4) -0.006(3) 0.005(2) C231 0.034(3) 0.023(3) 0.041(4) 0.004(3) 0.002(4) -0.001(2) C232 0.030(3) 0.017(3) 0.068(7) 0.012(5) -0.010(8) -0.006(3) C233 0.033(5) 0.038(4) 0.060(6) 0.015(4) -0.025(6) 0.005(3) C234 0.041(3) 0.043(5) 0.053(6) 0.014(4) -0.019(6) -0.005(4) C235 0.042(3) 0.046(4) 0.028(5) -0.005(5) -0.011(6) 0.008(3) C236 0.039(3) 0.036(4) 0.027(6) 0.001(4) -0.008(7) -0.001(3) C237 0.026(5) 0.034(4) 0.072(7) 0.006(5) -0.021(4) 0.013(4) C238 0.084(4) 0.076(7) 0.055(8) 0.022(5) -0.011(9) -0.013(5) C239 0.054(3) 0.037(4) 0.021(7) -0.002(5) -0.005(6) 0.007(3) C241 0.018(4) 0.027(3) 0.047(4) -0.007(4) 0.014(4) -0.002(3) C242 0.025(5) 0.037(3) 0.057(6) -0.009(4) 0.011(6) 0.004(2) C243 0.038(6) 0.037(3) 0.046(6) -0.015(4) 0.031(5) -0.005(3) C244 0.036(5) 0.058(4) 0.030(5) -0.008(4) 0.033(4) 0.000(3) C245 0.041(4) 0.043(3) 0.036(5) 0.005(4) 0.028(5) 0.000(3) C246 0.024(4) 0.026(3) 0.040(5) 0.002(4) 0.027(4) -0.005(3) C247 0.030(4) 0.020(4) 0.082(8) -0.012(7) 0.007(7) 0.001(3) C248 0.063(6) 0.092(5) 0.026(5) -0.007(5) 0.041(5) 0.000(4) C249 0.052(6) 0.035(4) 0.073(9) -0.012(4) 0.013(7) 0.009(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 N11 C100 1.340(6) . ? N11 N12 1.358(6) . ? N12 C111 1.316(6) . ? C100 N14 1.335(9) . ? C100 N13 1.384(8) . ? N13 C101 1.414(9) . ? N13 C131 1.434(10) . ? C101 C102 1.330(6) . ? C102 N14 1.368(9) . ? N14 C141 1.431(9) . ? C111 C112 1.429(7) . ? C111 C123 1.470(7) . ? C112 C113 1.386(7) . ? C112 C117 1.416(8) . ? C113 C114 1.371(7) . ? C114 C115 1.382(7) . ? C114 Cl11 1.745(6) . ? C115 C116 1.392(8) . ? C116 C117 1.412(7) . ? C117 C118 1.442(6) . ? C118 C119 1.352(7) . ? C118 C123 1.423(8) . ? C119 C120 1.378(8) . ? C120 C121 1.404(8) . ? C121 C122 1.360(8) . ? C121 Cl12 1.748(6) . ? C122 C123 1.401(8) . ? C131 C136 1.374(13) . ? C131 C132 1.387(13) . ? C132 C133 1.401(12) . ? C132 C137 1.504(14) . ? C133 C134 1.391(14) . ? C134 C135 1.361(11) . ? C134 C138 1.479(10) . ? C135 C136 1.353(10) . ? C136 C139 1.530(13) . ? C141 C142 1.392(13) . ? C141 C146 1.403(13) . ? C142 C143 1.365(11) . ? C142 C147 1.514(14) . ? C143 C144 1.372(14) . ? C144 C145 1.409(12) . ? C144 C148 1.525(11) . ? C145 C146 1.414(10) . ? C146 C149 1.481(12) . ? N21 C200 1.347(10) . ? N21 N22 1.365(10) . ? N22 C211 1.306(10) . ? C200 N24 1.337(13) . ? C200 N23 1.387(13) . ? N23 C201 1.422(13) . ? N23 C231 1.444(14) . ? C201 C202 1.330(12) . ? C202 N24 1.370(14) . ? N24 C241 1.434(14) . ? C211 C223 1.461(10) . ? C211 C212 1.438(9) . ? C212 C217 1.409(12) . ? C212 C213 1.417(10) . ? C213 C214 1.403(10) . ? C214 C215 1.396(10) . ? C214 Cl21 1.759(10) . ? C215 C216 1.413(10) . ? C216 C217 1.416(10) . ? C217 C218 1.450(9) . ? C218 C219 1.351(12) . ? C218 C223 1.421(12) . ? C219 C220 1.374(13) . ? C220 C221 1.407(13) . ? C221 C222 1.366(12) . ? C221 Cl22 1.724(10) . ? C222 C223 1.406(11) . ? C231 C236 1.384(18) . ? C231 C232 1.404(18) . ? C232 C233 1.409(16) . ? C232 C237 1.502(18) . ? C233 C234 1.384(19) . ? C234 C235 1.381(16) . ? C234 C238 1.485(15) . ? C235 C236 1.342(14) . ? C236 C239 1.537(17) . ? C241 C242 1.395(18) . ? C241 C246 1.404(18) . ? C242 C243 1.358(16) . ? C242 C247 1.511(19) . ? C243 C244 1.368(19) . ? C244 C245 1.408(17) . ? C244 C248 1.536(15) . ? C245 C246 1.419(14) . ? C246 C249 1.499(17) . ? 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 C100 N11 N12 112.9(6) . . ? C111 N12 N11 114.1(5) . . ? N14 C100 N11 119.2(6) . . ? N14 C100 N13 106.5(4) . . ? N11 C100 N13 134.0(6) . . ? C100 N13 C101 106.9(6) . . ? C100 N13 C131 127.7(7) . . ? C101 N13 C131 125.2(7) . . ? C102 C101 N13 108.0(7) . . ? C101 C102 N14 107.4(7) . . ? C100 N14 C102 111.1(6) . . ? C100 N14 C141 121.4(8) . . ? C102 N14 C141 126.4(8) . . ? N12 C111 C112 119.8(5) . . ? N12 C111 C123 131.3(5) . . ? C112 C111 C123 108.7(4) . . ? C113 C112 C117 120.3(6) . . ? C113 C112 C111 132.5(6) . . ? C117 C112 C111 107.1(5) . . ? C114 C113 C112 118.1(6) . . ? C113 C114 C115 123.3(6) . . ? C113 C114 Cl11 117.8(5) . . ? C115 C114 Cl11 118.8(5) . . ? C114 C115 C116 119.8(6) . . ? C115 C116 C117 118.1(7) . . ? C116 C117 C112 120.1(5) . . ? C116 C117 C118 130.3(6) . . ? C112 C117 C118 109.6(6) . . ? C119 C118 C123 119.0(5) . . ? C119 C118 C117 132.9(6) . . ? C123 C118 C117 108.0(5) . . ? C118 C119 C120 122.0(6) . . ? C119 C120 C121 118.6(5) . . ? C122 C121 C120 121.4(6) . . ? C122 C121 Cl12 119.9(5) . . ? C120 C121 Cl12 118.2(5) . . ? C121 C122 C123 119.2(6) . . ? C122 C123 C118 119.7(6) . . ? C122 C123 C111 133.8(5) . . ? C118 C123 C111 106.5(5) . . ? C136 C131 C132 122.0(8) . . ? C136 C131 N13 122.3(9) . . ? C132 C131 N13 115.7(9) . . ? C131 C132 C133 116.7(10) . . ? C131 C132 C137 120.2(9) . . ? C133 C132 C137 122.8(10) . . ? C134 C133 C132 122.6(9) . . ? C135 C134 C133 115.5(8) . . ? C135 C134 C138 126.4(10) . . ? C133 C134 C138 118.1(9) . . ? C136 C135 C134 125.4(9) . . ? C135 C136 C131 117.4(8) . . ? C135 C136 C139 121.0(9) . . ? C131 C136 C139 121.3(9) . . ? C142 C141 C146 121.4(8) . . ? C142 C141 N14 120.9(9) . . ? C146 C141 N14 117.6(9) . . ? C143 C142 C141 119.3(10) . . ? C143 C142 C147 119.3(9) . . ? C141 C142 C147 120.9(9) . . ? C142 C143 C144 121.8(9) . . ? C143 C144 C145 119.3(8) . . ? C143 C144 C148 122.3(10) . . ? C145 C144 C148 118.2(10) . . ? C144 C145 C146 119.9(9) . . ? C141 C146 C145 117.7(8) . . ? C141 C146 C149 123.2(7) . . ? C145 C146 C149 119.0(8) . . ? C200 N21 N22 115.8(11) . . ? C211 N22 N21 116.9(9) . . ? N24 C200 N21 119.3(11) . . ? N24 C200 N23 106.2(9) . . ? N21 C200 N23 133.5(11) . . ? C200 N23 C201 105.8(9) . . ? C200 N23 C231 127.9(15) . . ? C201 N23 C231 126.3(15) . . ? C202 C201 N23 108.7(11) . . ? C201 C202 N24 106.6(11) . . ? C200 N24 C202 111.2(11) . . ? C200 N24 C241 123.6(13) . . ? C202 N24 C241 125.2(13) . . ? N22 C211 C223 133.8(9) . . ? N22 C211 C212 120.1(9) . . ? C223 C211 C212 106.1(8) . . ? C217 C212 C213 119.4(9) . . ? C217 C212 C211 108.1(8) . . ? C213 C212 C211 132.5(10) . . ? C214 C213 C212 118.0(10) . . ? C215 C214 C213 123.2(10) . . ? C215 C214 Cl21 117.8(8) . . ? C213 C214 Cl21 118.9(8) . . ? C214 C215 C216 119.2(10) . . ? C217 C216 C215 118.3(11) . . ? C216 C217 C212 121.9(9) . . ? C216 C217 C218 128.4(11) . . ? C212 C217 C218 109.5(9) . . ? C219 C218 C223 115.3(10) . . ? C219 C218 C217 135.2(13) . . ? C223 C218 C217 105.5(10) . . ? C218 C219 C220 125.9(14) . . ? C219 C220 C221 113.7(11) . . ? C222 C221 C220 122.7(10) . . ? C222 C221 Cl22 118.6(9) . . ? C220 C221 Cl22 117.0(9) . . ? C221 C222 C223 116.9(11) . . ? C222 C223 C218 120.6(10) . . ? C222 C223 C211 129.6(9) . . ? C218 C223 C211 108.7(8) . . ? C236 C231 C232 122.9(13) . . ? C236 C231 N23 120.6(15) . . ? C232 C231 N23 116.4(15) . . ? C231 C232 C233 113.8(15) . . ? C231 C232 C237 120.2(14) . . ? C233 C232 C237 125.2(17) . . ? C234 C233 C232 125.0(16) . . ? C235 C234 C233 115.5(14) . . ? C235 C234 C238 122.9(18) . . ? C233 C234 C238 121.2(18) . . ? C236 C235 C234 123.6(16) . . ? C235 C236 C231 118.8(15) . . ? C235 C236 C239 122.6(15) . . ? C231 C236 C239 118.4(13) . . ? C242 C241 C246 120.5(12) . . ? C242 C241 N24 122.4(15) . . ? C246 C241 N24 117.1(15) . . ? C243 C242 C241 120.1(15) . . ? C243 C242 C247 120.4(17) . . ? C241 C242 C247 119.5(17) . . ? C242 C243 C244 121.4(16) . . ? C243 C244 C245 120.3(14) . . ? C243 C244 C248 122.6(15) . . ? C245 C244 C248 116.7(15) . . ? C244 C245 C246 118.8(15) . . ? C241 C246 C245 118.3(14) . . ? C241 C246 C249 120.7(15) . . ? C245 C246 C249 120.2(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 20.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.111 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.027 data_p1b _database_code_depnum_ccdc_archive 'CCDC 236036' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H30 Br2 N4' _chemical_formula_weight 654.44 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1477(7) _cell_length_b 20.9731(13) _cell_length_c 14.0060(8) _cell_angle_alpha 90.00 _cell_angle_beta 113.242(2) _cell_angle_gamma 90.00 _cell_volume 3008.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 2.724 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The crystal was coated in Nujol and placed rapidly in the 173K N2 boil-off cold stream ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28975 _diffrn_reflns_av_R_equivalents 0.1293 _diffrn_reflns_av_sigmaI/netI 0.1361 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6935 _reflns_number_gt 2909 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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. ; _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^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6935 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1996 _refine_ls_R_factor_gt 0.0845 _refine_ls_wR_factor_ref 0.2282 _refine_ls_wR_factor_gt 0.1859 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.028 _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 C01 C 0.3267(7) 0.0851(3) 0.1859(6) 0.0390(17) Uani 1 1 d . . . C03 C 0.2031(7) 0.0421(4) 0.2611(6) 0.046(2) Uani 1 1 d . . . H03 H 0.1750 0.0284 0.3120 0.056 Uiso 1 1 calc R . . C04 C 0.1354(8) 0.0385(4) 0.1585(6) 0.051(2) Uani 1 1 d . . . H04 H 0.0523 0.0213 0.1250 0.062 Uiso 1 1 calc R . . C11 C 0.5106(7) 0.1566(3) 0.0722(5) 0.0349(16) Uani 1 1 d . . . C12 C 0.6507(7) 0.1674(3) 0.1436(5) 0.0359(17) Uani 1 1 d . . . C13 C 0.7166(7) 0.1550(3) 0.2467(6) 0.0397(17) Uani 1 1 d . . . H13 H 0.6751 0.1361 0.2855 0.048 Uiso 1 1 calc R . . C14 C 0.8482(8) 0.1716(4) 0.2921(5) 0.045(2) Uani 1 1 d . . . C15 C 0.9133(7) 0.2007(3) 0.2365(6) 0.0413(18) Uani 1 1 d . . . H15 H 1.0014 0.2111 0.2688 0.050 Uiso 1 1 calc R . . C16 C 0.8436(7) 0.2139(3) 0.1321(6) 0.0438(19) Uani 1 1 d . . . H16 H 0.8851 0.2334 0.0939 0.053 Uiso 1 1 calc R . . C17 C 0.7114(7) 0.1979(3) 0.0839(6) 0.0379(17) Uani 1 1 d . . . C18 C 0.6170(7) 0.2057(3) -0.0217(6) 0.0392(17) Uani 1 1 d . . . C19 C 0.6248(8) 0.2329(4) -0.1087(6) 0.0452(19) Uani 1 1 d . . . H19 H 0.7030 0.2503 -0.1055 0.054 Uiso 1 1 calc R . . C21 C 0.4221(7) 0.0874(4) 0.3787(6) 0.045(2) Uani 1 1 d . . . C22 C 0.5407(9) 0.0546(4) 0.4129(7) 0.058(2) Uani 1 1 d . . . C23 C 0.6344(8) 0.0737(5) 0.5107(7) 0.064(3) Uani 1 1 d . . . H23 H 0.7161 0.0543 0.5354 0.076 Uiso 1 1 calc R . . C24 C 0.6104(9) 0.1195(4) 0.5706(7) 0.060(2) Uani 1 1 d . . . C25 C 0.4909(8) 0.1492(4) 0.5319(7) 0.056(2) Uani 1 1 d . . . H25 H 0.4731 0.1805 0.5714 0.068 Uiso 1 1 calc R . . C26 C 0.3961(7) 0.1335(4) 0.4355(6) 0.0447(19) Uani 1 1 d . . . C31 C 0.1796(7) 0.0590(3) 0.0007(6) 0.0429(18) Uani 1 1 d . . . C32 C 0.2360(8) 0.0093(4) -0.0332(6) 0.052(2) Uani 1 1 d . . . C33 C 0.2050(8) 0.0033(4) -0.1378(6) 0.056(2) Uani 1 1 d . . . H33 H 0.2438 -0.0291 -0.1609 0.067 Uiso 1 1 calc R . . C34 C 0.1172(8) 0.0442(4) -0.2106(6) 0.048(2) Uani 1 1 d . . . C35 C 0.0643(7) 0.0931(4) -0.1733(6) 0.047(2) Uani 1 1 d . . . H35 H 0.0076 0.1217 -0.2205 0.057 Uiso 1 1 calc R . . C36 C 0.0926(7) 0.1012(4) -0.0677(6) 0.0420(18) Uani 1 1 d . . . C110 C 0.5138(8) 0.2341(4) -0.2018(6) 0.054(2) Uani 1 1 d . . . H110 H 0.5179 0.2527 -0.2608 0.064 Uiso 1 1 calc R . . C111 C 0.3992(8) 0.2079(4) -0.2062(6) 0.050(2) Uani 1 1 d . . . C112 C 0.3863(8) 0.1804(4) -0.1237(6) 0.049(2) Uani 1 1 d . . . H112 H 0.3076 0.1622 -0.1298 0.058 Uiso 1 1 calc R . . C113 C 0.4946(7) 0.1800(3) -0.0288(6) 0.0372(17) Uani 1 1 d . . . C221 C 0.5685(9) 0.0023(5) 0.3514(8) 0.077(3) Uani 1 1 d . . . H22A H 0.4938 -0.0040 0.2876 0.115 Uiso 1 1 calc R . . H22B H 0.5871 -0.0365 0.3910 0.115 Uiso 1 1 calc R . . H22C H 0.6424 0.0138 0.3362 0.115 Uiso 1 1 calc R . . C241 C 0.7129(10) 0.1359(5) 0.6765(8) 0.096(4) Uani 1 1 d . . . H24A H 0.6808 0.1691 0.7072 0.143 Uiso 1 1 calc R . . H24B H 0.7908 0.1501 0.6693 0.143 Uiso 1 1 calc R . . H24C H 0.7322 0.0988 0.7201 0.143 Uiso 1 1 calc R . . C261 C 0.2668(7) 0.1687(4) 0.3941(6) 0.054(2) Uani 1 1 d . . . H26A H 0.2656 0.1994 0.4445 0.081 Uiso 1 1 calc R . . H26B H 0.1968 0.1388 0.3809 0.081 Uiso 1 1 calc R . . H26C H 0.2562 0.1901 0.3307 0.081 Uiso 1 1 calc R . . C321 C 0.3356(11) -0.0344(4) 0.0452(7) 0.085(3) Uani 1 1 d . . . H32A H 0.3448 -0.0230 0.1141 0.128 Uiso 1 1 calc R . . H32B H 0.4183 -0.0299 0.0396 0.128 Uiso 1 1 calc R . . H32C H 0.3067 -0.0778 0.0314 0.128 Uiso 1 1 calc R . . C341 C 0.0855(9) 0.0365(4) -0.3253(6) 0.066(3) Uani 1 1 d . . . H34A H 0.1315 0.0003 -0.3360 0.098 Uiso 1 1 calc R . . H34B H 0.1117 0.0742 -0.3511 0.098 Uiso 1 1 calc R . . H34C H -0.0067 0.0302 -0.3619 0.098 Uiso 1 1 calc R . . C361 C 0.0348(9) 0.1549(4) -0.0311(7) 0.069(3) Uani 1 1 d . . . H36A H -0.0226 0.1788 -0.0898 0.104 Uiso 1 1 calc R . . H36B H 0.1032 0.1822 0.0133 0.104 Uiso 1 1 calc R . . H36C H -0.0136 0.1383 0.0069 0.104 Uiso 1 1 calc R . . N1 N 0.4357(6) 0.1135(3) 0.1827(4) 0.0422(15) Uani 1 1 d . . . N2 N 0.4088(6) 0.1318(3) 0.0863(4) 0.0402(15) Uani 1 1 d . . . N02 N 0.3243(6) 0.0703(3) 0.2783(5) 0.0438(15) Uani 1 1 d . . . N05 N 0.2128(6) 0.0655(3) 0.1105(5) 0.0433(15) Uani 1 1 d . . . Br1 Br 0.94232(8) 0.15389(4) 0.43552(6) 0.0564(3) Uani 1 1 d . . . Br2 Br 0.24978(10) 0.20984(5) -0.33481(7) 0.0747(4) 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 C01 0.028(4) 0.033(4) 0.061(5) -0.006(4) 0.023(4) -0.001(3) C03 0.030(4) 0.061(5) 0.056(5) 0.003(4) 0.026(4) -0.011(4) C04 0.050(5) 0.054(5) 0.062(6) 0.008(4) 0.034(5) -0.008(4) C11 0.033(4) 0.032(4) 0.047(4) -0.005(3) 0.023(3) -0.001(3) C12 0.042(4) 0.029(4) 0.047(4) 0.002(3) 0.029(4) 0.001(3) C13 0.038(4) 0.036(4) 0.056(5) 0.001(4) 0.031(4) 0.000(4) C14 0.049(5) 0.052(5) 0.033(4) 0.010(4) 0.015(4) 0.025(4) C15 0.029(4) 0.050(5) 0.050(5) 0.000(4) 0.022(4) 0.006(3) C16 0.045(5) 0.043(5) 0.059(5) 0.008(4) 0.037(4) -0.001(4) C17 0.040(4) 0.034(4) 0.052(5) 0.000(3) 0.031(4) 0.002(3) C18 0.039(4) 0.033(4) 0.049(4) -0.002(3) 0.022(4) 0.000(3) C19 0.044(5) 0.047(5) 0.050(5) 0.006(4) 0.025(4) -0.017(4) C21 0.022(4) 0.063(5) 0.046(5) 0.017(4) 0.011(4) 0.000(4) C22 0.054(6) 0.052(5) 0.085(7) 0.024(5) 0.043(5) 0.007(4) C23 0.023(4) 0.090(7) 0.076(6) 0.043(6) 0.016(5) 0.003(5) C24 0.048(6) 0.055(5) 0.070(6) 0.016(5) 0.016(5) -0.008(5) C25 0.042(5) 0.055(5) 0.062(5) 0.014(4) 0.009(4) 0.002(4) C26 0.035(4) 0.052(5) 0.049(5) 0.009(4) 0.019(4) -0.006(4) C31 0.044(5) 0.030(4) 0.062(5) 0.001(4) 0.029(4) 0.000(4) C32 0.067(6) 0.034(4) 0.067(6) 0.000(4) 0.039(5) -0.002(4) C33 0.065(6) 0.047(5) 0.064(6) -0.010(4) 0.034(5) 0.008(4) C34 0.040(5) 0.053(5) 0.060(5) -0.009(4) 0.031(4) -0.012(4) C35 0.028(4) 0.043(5) 0.069(6) 0.007(4) 0.017(4) -0.006(3) C36 0.039(4) 0.046(5) 0.046(5) -0.006(4) 0.022(4) -0.004(4) C110 0.056(5) 0.063(6) 0.047(5) 0.007(4) 0.025(4) -0.023(4) C111 0.050(5) 0.054(5) 0.040(4) 0.007(4) 0.011(4) -0.002(4) C112 0.040(5) 0.048(5) 0.058(5) -0.008(4) 0.019(4) -0.012(4) C113 0.037(4) 0.029(4) 0.058(5) -0.005(3) 0.032(4) -0.006(3) C221 0.067(7) 0.068(7) 0.111(8) 0.021(6) 0.052(6) 0.010(5) C241 0.058(6) 0.077(7) 0.100(8) 0.017(6) -0.024(6) -0.021(5) C261 0.038(5) 0.065(6) 0.062(5) 0.000(4) 0.022(4) 0.001(4) C321 0.129(10) 0.045(6) 0.089(7) 0.008(5) 0.050(7) 0.046(6) C341 0.069(6) 0.073(6) 0.063(6) -0.005(5) 0.036(5) -0.012(5) C361 0.054(6) 0.063(6) 0.088(7) -0.015(5) 0.025(5) 0.013(5) N1 0.037(4) 0.045(4) 0.042(4) 0.003(3) 0.013(3) 0.007(3) N2 0.048(4) 0.035(3) 0.039(4) 0.000(3) 0.020(3) 0.009(3) N02 0.039(4) 0.048(4) 0.053(4) 0.007(3) 0.028(3) -0.001(3) N05 0.057(4) 0.039(4) 0.048(4) 0.001(3) 0.036(4) 0.000(3) Br1 0.0487(5) 0.0706(6) 0.0501(5) 0.0130(4) 0.0198(4) 0.0126(4) Br2 0.0607(6) 0.0936(8) 0.0555(6) 0.0085(5) 0.0075(5) -0.0183(5) _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 C01 N02 1.342(9) . ? C01 N05 1.356(9) . ? C01 N1 1.370(9) . ? C03 C04 1.335(10) . ? C03 N02 1.405(9) . ? C04 N05 1.406(9) . ? C11 N2 1.331(9) . ? C11 C113 1.440(10) . ? C11 C12 1.503(10) . ? C12 C13 1.363(10) . ? C12 C17 1.419(9) . ? C13 C14 1.393(10) . ? C14 C15 1.398(10) . ? C14 Br1 1.900(7) . ? C15 C16 1.385(10) . ? C16 C17 1.398(10) . ? C17 C18 1.447(10) . ? C18 C19 1.378(9) . ? C18 C113 1.434(9) . ? C19 C110 1.400(11) . ? C21 C26 1.354(10) . ? C21 C22 1.397(11) . ? C21 N02 1.444(9) . ? C22 C23 1.414(12) . ? C22 C221 1.501(12) . ? C23 C24 1.371(13) . ? C24 C25 1.372(12) . ? C24 C241 1.511(12) . ? C25 C26 1.386(10) . ? C26 C261 1.517(10) . ? C31 C36 1.383(10) . ? C31 C32 1.395(10) . ? C31 N05 1.438(9) . ? C32 C33 1.371(11) . ? C32 C321 1.521(11) . ? C33 C34 1.396(11) . ? C34 C35 1.384(10) . ? C34 C341 1.511(10) . ? C35 C36 1.396(10) . ? C36 C361 1.485(10) . ? C110 C111 1.370(11) . ? C111 C112 1.348(10) . ? C111 Br2 1.912(8) . ? C112 C113 1.399(10) . ? N1 N2 1.319(7) . ? 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 N02 C01 N05 108.2(6) . . ? N02 C01 N1 119.3(7) . . ? N05 C01 N1 132.5(7) . . ? C04 C03 N02 107.8(6) . . ? C03 C04 N05 107.4(7) . . ? N2 C11 C113 119.8(6) . . ? N2 C11 C12 133.0(6) . . ? C113 C11 C12 107.2(6) . . ? C13 C12 C17 121.9(7) . . ? C13 C12 C11 131.3(6) . . ? C17 C12 C11 106.8(6) . . ? C12 C13 C14 117.8(7) . . ? C13 C14 C15 122.7(7) . . ? C13 C14 Br1 118.5(6) . . ? C15 C14 Br1 118.9(6) . . ? C16 C15 C14 118.5(7) . . ? C15 C16 C17 120.5(7) . . ? C16 C17 C12 118.7(7) . . ? C16 C17 C18 132.1(6) . . ? C12 C17 C18 109.2(6) . . ? C19 C18 C113 119.0(7) . . ? C19 C18 C17 132.5(7) . . ? C113 C18 C17 108.4(6) . . ? C18 C19 C110 119.4(7) . . ? C26 C21 C22 122.9(8) . . ? C26 C21 N02 119.7(7) . . ? C22 C21 N02 117.4(8) . . ? C21 C22 C23 115.5(8) . . ? C21 C22 C221 123.0(9) . . ? C23 C22 C221 121.5(8) . . ? C24 C23 C22 122.9(8) . . ? C25 C24 C23 118.0(9) . . ? C25 C24 C241 121.7(10) . . ? C23 C24 C241 120.3(9) . . ? C24 C25 C26 121.7(9) . . ? C21 C26 C25 119.0(7) . . ? C21 C26 C261 121.0(7) . . ? C25 C26 C261 120.0(7) . . ? C36 C31 C32 122.0(7) . . ? C36 C31 N05 119.6(6) . . ? C32 C31 N05 118.3(7) . . ? C33 C32 C31 118.3(8) . . ? C33 C32 C321 121.4(7) . . ? C31 C32 C321 120.2(7) . . ? C32 C33 C34 122.3(8) . . ? C35 C34 C33 117.4(7) . . ? C35 C34 C341 121.6(8) . . ? C33 C34 C341 121.0(7) . . ? C34 C35 C36 122.6(7) . . ? C31 C36 C35 117.4(7) . . ? C31 C36 C361 121.8(7) . . ? C35 C36 C361 120.8(7) . . ? C111 C110 C19 120.0(7) . . ? C112 C111 C110 123.1(7) . . ? C112 C111 Br2 118.0(6) . . ? C110 C111 Br2 118.9(6) . . ? C111 C112 C113 118.2(7) . . ? C112 C113 C18 120.2(6) . . ? C112 C113 C11 131.4(6) . . ? C18 C113 C11 108.4(6) . . ? N2 N1 C01 108.3(6) . . ? N1 N2 C11 113.8(6) . . ? C01 N02 C03 108.4(6) . . ? C01 N02 C21 125.9(6) . . ? C03 N02 C21 125.3(6) . . ? C01 N05 C04 108.2(6) . . ? C01 N05 C31 129.0(6) . . ? C04 N05 C31 121.6(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.164 _refine_diff_density_min -0.784 _refine_diff_density_rms 0.123 data_dd1 _database_code_depnum_ccdc_archive 'CCDC 236037' _audit_creation_method SHELXL-97 _chemical_name_systematic ; CLB Macdonald for JAC Clyburne - DD1 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H34 F N4' _chemical_formula_weight 553.68 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' F F 0.0171 0.0103 '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 10.5060(6) _cell_length_b 11.5012(7) _cell_length_c 25.6373(16) _cell_angle_alpha 80.3250(10) _cell_angle_beta 81.3250(10) _cell_angle_gamma 89.4250(10) _cell_volume 3018.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6421 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour yellow/orang _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 26256 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 0.82 _diffrn_reflns_theta_max 27.49 _reflns_number_total 13150 _reflns_number_gt 9662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0713P)^2^+2.2321P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13150 _refine_ls_number_parameters 769 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0992 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.1929 _refine_ls_wR_factor_gt 0.1807 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 3.569 _refine_ls_shift/su_mean 0.043 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 C1 C -0.1334(2) 1.2169(2) 0.27786(11) 0.0376(5) Uani 1 1 d . . . C11 C 0.1325(2) 1.3755(2) 0.21192(11) 0.0399(6) Uani 1 1 d . . . C12 C 0.2142(3) 1.3948(2) 0.16020(11) 0.0451(6) Uani 1 1 d . . . C13 C 0.2031(3) 1.3596(3) 0.11209(12) 0.0564(7) Uani 1 1 d . . . H13A H 0.1281 1.3181 0.1084 0.068 Uiso 1 1 calc R . . C14 C 0.3004(4) 1.3846(3) 0.06979(15) 0.0691(9) Uani 1 1 d . . . C15 C 0.4097(4) 1.4452(3) 0.07486(14) 0.0688(9) Uani 1 1 d . . . H15A H 0.4775 1.4603 0.0455 0.083 Uiso 1 1 calc R . . C16 C 0.4217(3) 1.4840(3) 0.12203(13) 0.0576(8) Uani 1 1 d . . . H16A H 0.4962 1.5276 0.1246 0.069 Uiso 1 1 calc R . . C17 C 0.3256(3) 1.4593(2) 0.16518(12) 0.0457(6) Uani 1 1 d . . . C18 C 0.3122(2) 1.4845(2) 0.21949(12) 0.0432(6) Uani 1 1 d . . . C19 C 0.3938(3) 1.5448(2) 0.24445(13) 0.0509(7) Uani 1 1 d . . . H19A H 0.4727 1.5784 0.2249 0.061 Uiso 1 1 calc R . . C110 C 0.3595(3) 1.5554(2) 0.29733(14) 0.0553(8) Uani 1 1 d . . . H11A H 0.4142 1.5956 0.3150 0.066 Uiso 1 1 calc R . . C111 C 0.2408(3) 1.5049(2) 0.32486(13) 0.0501(7) Uani 1 1 d . . . C112 C 0.1603(2) 1.4457(2) 0.30112(12) 0.0439(6) Uani 1 1 d . . . H11B H 0.0815 1.4128 0.3209 0.053 Uiso 1 1 calc R . . C113 C 0.1938(2) 1.4340(2) 0.24837(11) 0.0394(6) Uani 1 1 d . . . C114 C -0.2889(2) 1.0951(2) 0.32659(12) 0.0455(6) Uani 1 1 d . . . H11C H -0.3429 1.0518 0.3565 0.055 Uiso 1 1 calc R . . C115 C -0.2930(2) 1.0905(2) 0.27551(12) 0.0446(6) Uani 1 1 d . . . H11D H -0.3510 1.0439 0.2623 0.054 Uiso 1 1 calc R . . 116 C -0.1449(2) 1.2029(2) 0.37488(11) 0.0452(6) Uani 1 1 d . . . 117 C -0.0601(3) 1.1264(3) 0.39920(12) 0.0544(8) Uani 1 1 d . . . 118 C -0.0076(3) 1.1608(4) 0.44091(13) 0.0690(10) Uani 1 1 d . . . H18A H 0.0506 1.1097 0.4582 0.083 Uiso 1 1 calc R . . 119 C -0.0371(4) 1.2662(4) 0.45798(13) 0.0720(10) Uani 1 1 d . . . 120 C -0.1250(3) 1.3387(3) 0.43355(13) 0.0651(9) Uani 1 1 d . . . H20A H -0.1478 1.4107 0.4458 0.078 Uiso 1 1 calc R . . 121 C -0.1805(3) 1.3089(3) 0.39154(12) 0.0516(7) Uani 1 1 d . . . 122 C -0.0277(3) 1.0105(3) 0.38088(14) 0.0669(9) Uani 1 1 d . . . H12A H -0.0740 1.0027 0.3512 0.100 Uiso 0.50 1 calc PR . . H12B H -0.0532 0.9457 0.4106 0.100 Uiso 0.50 1 calc PR . . H12C H 0.0652 1.0078 0.3689 0.100 Uiso 0.50 1 calc PR . . H12D H 0.0327 0.9681 0.4026 0.100 Uiso 0.50 1 calc PR . . H12E H 0.0119 1.0251 0.3432 0.100 Uiso 0.50 1 calc PR . . H12F H -0.1065 0.9630 0.3849 0.100 Uiso 0.50 1 calc PR . . 123 C 0.0256(5) 1.3042(5) 0.50221(16) 0.1081(17) Uani 1 1 d . . . H23A H 0.0850 1.2432 0.5148 0.162 Uiso 1 1 calc R . . H23B H -0.0410 1.3154 0.5320 0.162 Uiso 1 1 calc R . . H23C H 0.0733 1.3785 0.4884 0.162 Uiso 1 1 calc R . . 124 C -0.2719(3) 1.3900(3) 0.36430(15) 0.0648(9) Uani 1 1 d . . . H12G H -0.2853 1.4597 0.3817 0.097 Uiso 0.50 1 calc PR . . H12H H -0.3544 1.3488 0.3669 0.097 Uiso 0.50 1 calc PR . . H12I H -0.2357 1.4144 0.3265 0.097 Uiso 0.50 1 calc PR . . H12J H -0.2983 1.3556 0.3350 0.097 Uiso 0.50 1 calc PR . . H12K H -0.2292 1.4665 0.3499 0.097 Uiso 0.50 1 calc PR . . H12L H -0.3479 1.4009 0.3902 0.097 Uiso 0.50 1 calc PR . . 125 C -0.1869(2) 1.2047(2) 0.18740(10) 0.0385(5) Uani 1 1 d . . . 126 C -0.1206(2) 1.1364(2) 0.15262(11) 0.0431(6) Uani 1 1 d . . . 127 C -0.1055(3) 1.1807(2) 0.09837(12) 0.0475(7) Uani 1 1 d . . . H27A H -0.0594 1.1359 0.0740 0.057 Uiso 1 1 calc R . . 128 C -0.1554(3) 1.2888(2) 0.07830(11) 0.0473(6) Uani 1 1 d . . . 129 C -0.2264(3) 1.3503(2) 0.11460(11) 0.0455(6) Uani 1 1 d . . . H29A H -0.2650 1.4221 0.1014 0.055 Uiso 1 1 calc R . . 130 C -0.2430(2) 1.3111(2) 0.16925(11) 0.0411(6) Uani 1 1 d . . . 131 C -0.0666(3) 1.0187(3) 0.17350(13) 0.0578(8) Uani 1 1 d . . . H13B H -0.0868 1.0027 0.2126 0.087 Uiso 0.50 1 calc PR . . H13C H 0.0270 1.0204 0.1628 0.087 Uiso 0.50 1 calc PR . . H13D H -0.1050 0.9567 0.1587 0.087 Uiso 0.50 1 calc PR . . H13E H -0.0230 0.9838 0.1434 0.087 Uiso 0.50 1 calc PR . . H13F H -0.1369 0.9661 0.1933 0.087 Uiso 0.50 1 calc PR . . H13G H -0.0049 1.0298 0.1974 0.087 Uiso 0.50 1 calc PR . . 132 C -0.1315(4) 1.3386(3) 0.01923(13) 0.0689(9) Uani 1 1 d . . . H32A H -0.1739 1.4149 0.0129 0.103 Uiso 1 1 calc R . . H32B H -0.1663 1.2840 -0.0007 0.103 Uiso 1 1 calc R . . H32C H -0.0386 1.3495 0.0072 0.103 Uiso 1 1 calc R . . 133 C -0.3169(3) 1.3821(2) 0.20756(12) 0.0547(7) Uani 1 1 d . . . H33A H -0.3487 1.4537 0.1874 0.082 Uiso 1 1 calc R . . H33B H -0.2602 1.4039 0.2315 0.082 Uiso 1 1 calc R . . H33C H -0.3899 1.3350 0.2287 0.082 Uiso 1 1 calc R . . C2 C 0.3836(2) 0.96521(19) 0.25711(9) 0.0323(5) Uani 1 1 d . . . C21 C 0.6402(2) 0.78311(19) 0.24035(10) 0.0330(5) Uani 1 1 d . . . C22 C 0.7169(2) 0.7303(2) 0.19829(10) 0.0358(5) Uani 1 1 d . . . C23 C 0.6986(3) 0.7248(2) 0.14663(10) 0.0415(6) Uani 1 1 d . . . H23D H 0.6260 0.7600 0.1326 0.050 Uiso 1 1 calc R . . C24 C 0.7885(3) 0.6667(2) 0.11596(12) 0.0514(7) Uani 1 1 d . . . C25 C 0.8957(3) 0.6142(2) 0.13481(13) 0.0528(7) Uani 1 1 d . . . H25A H 0.9556 0.5750 0.1124 0.063 Uiso 1 1 calc R . . C26 C 0.9144(2) 0.6197(2) 0.18653(13) 0.0489(7) Uani 1 1 d . . . H26A H 0.9873 0.5840 0.2001 0.059 Uiso 1 1 calc R . . C27 C 0.8262(2) 0.6775(2) 0.21850(11) 0.0396(6) Uani 1 1 d . . . C28 C 0.8185(2) 0.6955(2) 0.27379(11) 0.0407(6) Uani 1 1 d . . . C29 C 0.9021(3) 0.6632(2) 0.31077(13) 0.0527(7) Uani 1 1 d . . . H29B H 0.9800 0.6244 0.3009 0.063 Uiso 1 1 calc R . . C210 C 0.8708(3) 0.6880(3) 0.36163(14) 0.0610(8) Uani 1 1 d . . . H21A H 0.9273 0.6660 0.3871 0.073 Uiso 1 1 calc R . . C211 C 0.7568(3) 0.7450(3) 0.37606(15) 0.0583(8) Uani 1 1 d . . . C212 C 0.6730(3) 0.7798(2) 0.33957(11) 0.0454(6) Uani 1 1 d . . . H21B H 0.5955 0.8191 0.3498 0.054 Uiso 1 1 calc R . . C213 C 0.7043(2) 0.7564(2) 0.28835(10) 0.0361(5) Uani 1 1 d . . . C214 C 0.2290(2) 1.1006(2) 0.26592(11) 0.0417(6) Uani 1 1 d . . . H21C H 0.1706 1.1537 0.2812 0.050 Uiso 1 1 calc R . . C215 C 0.2439(2) 1.0830(2) 0.21582(11) 0.0432(6) Uani 1 1 d . . . H21D H 0.1979 1.1211 0.1887 0.052 Uiso 1 1 calc R . . 216 C 0.3269(2) 1.0203(2) 0.34769(10) 0.0355(5) Uani 1 1 d . . . 217 C 0.2904(2) 0.9169(2) 0.38368(11) 0.0406(6) Uani 1 1 d . . . 218 C 0.2965(3) 0.9162(3) 0.43724(11) 0.0479(7) Uani 1 1 d . . . H18B H 0.2731 0.8460 0.4621 0.058 Uiso 1 1 calc R . . 219 C 0.3356(3) 1.0144(3) 0.45591(11) 0.0503(7) Uani 1 1 d . . . 220 C 0.3716(2) 1.1150(3) 0.41892(12) 0.0474(7) Uani 1 1 d . . . H20B H 0.3995 1.1827 0.4311 0.057 Uiso 1 1 calc R . . 221 C 0.3684(2) 1.1204(2) 0.36465(11) 0.0394(6) Uani 1 1 d . . . 222 C 0.2426(3) 0.8099(2) 0.36522(12) 0.0523(7) Uani 1 1 d . . . H22D H 0.2219 0.7464 0.3960 0.078 Uiso 1 1 calc R . . H22E H 0.3096 0.7838 0.3389 0.078 Uiso 1 1 calc R . . H22F H 0.1652 0.8300 0.3487 0.078 Uiso 1 1 calc R . . 223 C 0.3345(3) 1.0122(4) 0.51498(13) 0.0722(10) Uani 1 1 d . . . H23E H 0.3066 0.9339 0.5347 0.108 Uiso 1 1 calc R . . H23F H 0.2749 1.0716 0.5272 0.108 Uiso 1 1 calc R . . H23G H 0.4213 1.0298 0.5214 0.108 Uiso 1 1 calc R . . 224 C 0.4101(3) 1.2314(2) 0.32557(12) 0.0504(7) Uani 1 1 d . . . H22A H 0.4358 1.2916 0.3450 0.076 Uiso 0.50 1 calc PR . . H22B H 0.3384 1.2604 0.3068 0.076 Uiso 0.50 1 calc PR . . H22C H 0.4831 1.2142 0.2995 0.076 Uiso 0.50 1 calc PR . . H22G H 0.4024 1.2192 0.2892 0.076 Uiso 0.50 1 calc PR . . H22H H 0.4998 1.2504 0.3274 0.076 Uiso 0.50 1 calc PR . . H22I H 0.3551 1.2966 0.3347 0.076 Uiso 0.50 1 calc PR . . 225 C 0.3679(2) 0.9452(2) 0.16198(10) 0.0366(5) Uani 1 1 d . . . 226 C 0.2982(2) 0.8451(2) 0.15899(11) 0.0425(6) Uani 1 1 d . . . 227 C 0.3287(3) 0.7943(2) 0.11347(12) 0.0514(7) Uani 1 1 d . . . H27B H 0.2827 0.7256 0.1105 0.062 Uiso 1 1 calc R . . 228 C 0.4243(3) 0.8406(3) 0.07213(11) 0.0538(8) Uani 1 1 d . . . 229 C 0.4894(3) 0.9417(3) 0.07652(11) 0.0494(7) Uani 1 1 d . . . H29C H 0.5544 0.9746 0.0481 0.059 Uiso 1 1 calc R . . 230 C 0.4627(2) 0.9965(2) 0.12106(10) 0.0408(6) Uani 1 1 d . . . 231 C 0.1972(3) 0.7918(2) 0.20444(13) 0.0557(8) Uani 1 1 d . . . H31D H 0.1585 0.7223 0.1952 0.084 Uiso 1 1 calc R . . H31E H 0.1304 0.8500 0.2110 0.084 Uiso 1 1 calc R . . H31F H 0.2369 0.7685 0.2368 0.084 Uiso 1 1 calc R . . 232 C 0.4606(5) 0.7802(3) 0.02406(14) 0.0848(12) Uani 1 1 d . . . H32D H 0.5300 0.8252 -0.0007 0.127 Uiso 1 1 calc R . . H32E H 0.3854 0.7762 0.0059 0.127 Uiso 1 1 calc R . . H32F H 0.4898 0.7003 0.0358 0.127 Uiso 1 1 calc R . . 233 C 0.5366(3) 1.1046(3) 0.12670(12) 0.0566(8) Uani 1 1 d . . . H23H H 0.5034 1.1294 0.1609 0.085 Uiso 0.50 1 calc PR . . H23I H 0.5263 1.1685 0.0972 0.085 Uiso 0.50 1 calc PR . . H23J H 0.6281 1.0859 0.1257 0.085 Uiso 0.50 1 calc PR . . H23K H 0.6018 1.1264 0.0950 0.085 Uiso 0.50 1 calc PR . . H23L H 0.5788 1.0874 0.1587 0.085 Uiso 0.50 1 calc PR . . H23M H 0.4771 1.1700 0.1301 0.085 Uiso 0.50 1 calc PR . . N11 N 0.0280(2) 1.30757(18) 0.22042(9) 0.0419(5) Uani 1 1 d . . . N12 N -0.0325(2) 1.29129(19) 0.27088(9) 0.0429(5) Uani 1 1 d . . . N13 N -0.19141(19) 1.17451(18) 0.32854(9) 0.0416(5) Uani 1 1 d . . . N14 N -0.19680(19) 1.16656(17) 0.24438(9) 0.0396(5) Uani 1 1 d . . . N21 N 0.53904(18) 0.84554(16) 0.23061(8) 0.0336(4) Uani 1 1 d . . . N22 N 0.47733(18) 0.89369(16) 0.27217(8) 0.0347(4) Uani 1 1 d . . . N23 N 0.33928(19) 0.99803(17) 0.20941(8) 0.0370(5) Uani 1 1 d . . . N24 N 0.31414(18) 1.02743(17) 0.29250(8) 0.0353(4) Uani 1 1 d . . . C41 C -0.1093(3) 0.9337(3) 0.02129(14) 0.0635(8) Uani 1 1 d . . . H41A H -0.1850 0.8881 0.0360 0.076 Uiso 1 1 calc R . . C42 C 0.0014(4) 0.9109(3) 0.04286(13) 0.0607(8) Uani 1 1 d . . . H42A H 0.0026 0.8491 0.0725 0.073 Uiso 1 1 calc R . . C43 C 0.1110(3) 0.9772(3) 0.02188(14) 0.0620(8) Uani 1 1 d . . . H43A H 0.1878 0.9616 0.0371 0.074 Uiso 1 1 calc R . . C31 C 0.4289(6) 0.4438(6) 0.4720(3) 0.130(2) Uani 1 1 d . . . H31G H 0.3774 0.4036 0.4530 0.156 Uiso 1 1 calc R . . C32 C 0.4239(6) 0.5613(6) 0.4671(2) 0.1176(18) Uani 1 1 d . . . H32G H 0.3723 0.6046 0.4434 0.141 Uiso 1 1 calc R . . C33 C 0.4923(7) 0.6188(5) 0.4960(3) 0.129(2) Uani 1 1 d . . . H33G H 0.4856 0.7018 0.4941 0.155 Uiso 1 1 calc R . . F1 F 0.2095(2) 1.5162(2) 0.37559(11) 0.0670(8) Uani 0.807(6) 1 d P . . F1A F 0.2811(10) 1.3602(8) 0.0258(4) 0.0670(8) Uani 0.193(6) 1 d P . . F2 F 0.7710(3) 0.6570(3) 0.06713(16) 0.0653(9) Uani 0.631(4) 1 d P . . F2A F 0.7364(5) 0.7739(5) 0.42037(19) 0.0653(9) Uani 0.369(4) 1 d P . . H14 H 0.2919 1.3614 0.0375 0.25(10) Uiso 0.807(6) 1 d P . . H111 H 0.2192 1.5117 0.3612 2.0(5) Uiso 0.193(6) 1 d P . . H211 H 0.7359 0.7577 0.4114 0.31(12) Uiso 0.631(4) 1 d P . . H24 H 0.7750 0.6613 0.0810 0.00(2) Uiso 0.369(4) 1 d P . . 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 C1 0.0288(12) 0.0302(12) 0.0545(16) -0.0065(11) -0.0098(11) 0.0041(9) C11 0.0341(13) 0.0311(12) 0.0555(16) -0.0027(11) -0.0155(11) 0.0081(10) C12 0.0451(15) 0.0317(13) 0.0531(16) 0.0059(11) -0.0053(12) 0.0071(11) C13 0.0635(19) 0.0555(18) 0.0528(18) -0.0071(14) -0.0200(15) 0.0093(15) C14 0.083(3) 0.071(2) 0.0488(19) 0.0000(16) -0.0059(17) 0.0086(19) C15 0.071(2) 0.068(2) 0.058(2) 0.0049(17) 0.0034(17) 0.0014(18) C16 0.0507(17) 0.0457(16) 0.068(2) 0.0065(14) 0.0005(15) -0.0001(13) C17 0.0414(14) 0.0307(13) 0.0612(18) 0.0031(12) -0.0080(12) 0.0042(10) C18 0.0272(12) 0.0244(11) 0.0731(19) 0.0021(11) -0.0039(12) 0.0042(9) C19 0.0356(14) 0.0339(13) 0.079(2) -0.0091(13) 0.0032(13) 0.0032(11) C110 0.0450(16) 0.0388(15) 0.087(2) -0.0228(15) -0.0129(15) 0.0046(12) C111 0.0508(16) 0.0430(15) 0.0593(18) -0.0180(13) -0.0085(14) 0.0176(13) C112 0.0366(13) 0.0316(13) 0.0650(18) -0.0096(12) -0.0116(12) 0.0060(10) C113 0.0344(12) 0.0280(12) 0.0536(16) -0.0032(11) -0.0049(11) 0.0098(10) C114 0.0344(13) 0.0393(14) 0.0592(18) 0.0028(12) -0.0074(12) -0.0066(11) C115 0.0351(13) 0.0333(13) 0.0640(18) -0.0016(12) -0.0099(12) -0.0092(10) 116 0.0347(13) 0.0510(16) 0.0474(15) 0.0000(12) -0.0065(11) -0.0114(11) 117 0.0310(13) 0.069(2) 0.0555(18) 0.0086(15) -0.0036(12) -0.0030(13) 118 0.0430(17) 0.101(3) 0.057(2) 0.0149(19) -0.0161(14) -0.0123(17) 119 0.064(2) 0.100(3) 0.0500(19) -0.0004(19) -0.0133(16) -0.029(2) 120 0.065(2) 0.071(2) 0.059(2) -0.0119(16) -0.0075(16) -0.0233(17) 121 0.0454(15) 0.0515(17) 0.0561(17) -0.0041(13) -0.0070(13) -0.0141(13) 122 0.0419(16) 0.073(2) 0.076(2) 0.0089(18) -0.0047(15) 0.0164(15) 123 0.102(3) 0.158(5) 0.067(3) -0.006(3) -0.035(2) -0.046(3) 124 0.072(2) 0.0458(17) 0.082(2) -0.0143(16) -0.0223(18) 0.0001(15) 125 0.0352(12) 0.0319(12) 0.0504(15) -0.0079(11) -0.0110(11) -0.0024(10) 126 0.0412(14) 0.0345(13) 0.0601(17) -0.0153(12) -0.0200(12) 0.0028(11) 127 0.0497(16) 0.0428(15) 0.0571(17) -0.0227(13) -0.0154(13) 0.0065(12) 128 0.0539(16) 0.0398(14) 0.0517(16) -0.0103(12) -0.0159(13) -0.0025(12) 129 0.0476(15) 0.0311(13) 0.0583(17) -0.0042(12) -0.0139(13) 0.0026(11) 130 0.0367(13) 0.0316(12) 0.0545(16) -0.0053(11) -0.0078(11) 0.0001(10) 131 0.0659(19) 0.0452(16) 0.068(2) -0.0149(14) -0.0245(16) 0.0200(14) 132 0.094(3) 0.059(2) 0.056(2) -0.0143(16) -0.0138(18) 0.0063(18) 133 0.0585(18) 0.0387(15) 0.0600(18) -0.0009(13) 0.0039(14) 0.0122(13) C2 0.0328(12) 0.0239(11) 0.0393(13) -0.0017(9) -0.0068(10) 0.0001(9) C21 0.0327(12) 0.0248(11) 0.0423(13) -0.0043(9) -0.0100(10) -0.0017(9) C22 0.0325(12) 0.0255(11) 0.0476(14) -0.0038(10) -0.0032(10) -0.0015(9) C23 0.0458(14) 0.0312(12) 0.0456(15) -0.0026(11) -0.0055(11) -0.0006(10) C24 0.0621(18) 0.0387(14) 0.0505(17) -0.0096(12) 0.0034(14) -0.0036(13) C25 0.0459(16) 0.0383(14) 0.071(2) -0.0154(14) 0.0099(14) 0.0015(12) C26 0.0331(13) 0.0354(14) 0.078(2) -0.0116(13) -0.0047(13) 0.0043(10) C27 0.0325(12) 0.0272(12) 0.0597(16) -0.0069(11) -0.0087(11) -0.0020(9) C28 0.0311(12) 0.0249(11) 0.0679(18) -0.0069(11) -0.0144(12) 0.0016(9) C29 0.0451(15) 0.0373(14) 0.082(2) -0.0129(14) -0.0282(15) 0.0104(12) C210 0.066(2) 0.0498(17) 0.078(2) -0.0118(16) -0.0453(17) 0.0105(15) C211 0.071(2) 0.0499(17) 0.064(2) -0.0190(15) -0.0312(16) 0.0072(15) C212 0.0468(15) 0.0376(14) 0.0563(17) -0.0116(12) -0.0187(13) 0.0060(11) C213 0.0352(12) 0.0247(11) 0.0512(15) -0.0067(10) -0.0149(11) 0.0015(9) C214 0.0364(13) 0.0330(13) 0.0541(16) -0.0022(11) -0.0086(11) 0.0109(10) C215 0.0383(13) 0.0360(13) 0.0553(17) -0.0012(12) -0.0150(12) 0.0121(10) 216 0.0288(11) 0.0344(12) 0.0421(14) -0.0054(10) -0.0034(10) 0.0099(9) 217 0.0323(12) 0.0348(13) 0.0507(16) -0.0026(11) 0.0006(11) 0.0072(10) 218 0.0389(14) 0.0505(16) 0.0473(16) 0.0048(12) 0.0013(12) 0.0071(12) 219 0.0331(13) 0.072(2) 0.0453(16) -0.0120(14) -0.0024(11) 0.0082(13) 220 0.0360(14) 0.0515(16) 0.0588(18) -0.0226(14) -0.0055(12) 0.0049(12) 221 0.0281(12) 0.0355(13) 0.0551(16) -0.0101(11) -0.0051(11) 0.0082(10) 222 0.0552(17) 0.0336(14) 0.0629(18) -0.0057(12) 0.0050(14) -0.0024(12) 223 0.0555(19) 0.112(3) 0.0491(18) -0.0217(19) 0.0005(15) 0.0015(19) 224 0.0456(15) 0.0333(13) 0.073(2) -0.0063(13) -0.0145(14) 0.0034(11) 225 0.0375(13) 0.0314(12) 0.0424(14) -0.0024(10) -0.0154(11) 0.0062(10) 226 0.0399(14) 0.0317(12) 0.0572(16) -0.0006(11) -0.0196(12) 0.0057(10) 227 0.0642(18) 0.0329(14) 0.0639(19) -0.0073(13) -0.0325(15) 0.0047(12) 228 0.080(2) 0.0439(16) 0.0427(16) -0.0091(12) -0.0267(15) 0.0173(15) 229 0.0564(17) 0.0508(16) 0.0394(15) 0.0014(12) -0.0127(12) 0.0078(13) 230 0.0433(14) 0.0406(14) 0.0391(14) -0.0008(11) -0.0143(11) 0.0020(11) 231 0.0451(16) 0.0384(15) 0.082(2) -0.0012(14) -0.0121(15) -0.0034(12) 232 0.149(4) 0.057(2) 0.053(2) -0.0150(16) -0.024(2) 0.014(2) 233 0.0612(18) 0.0610(19) 0.0460(16) -0.0029(14) -0.0079(14) -0.0222(15) N11 0.0407(12) 0.0358(11) 0.0506(13) -0.0045(9) -0.0152(10) 0.0054(9) N12 0.0331(11) 0.0404(12) 0.0523(14) -0.0031(10) -0.0030(10) 0.0030(9) N13 0.0327(11) 0.0376(11) 0.0527(13) -0.0008(10) -0.0083(9) -0.0039(9) N14 0.0351(11) 0.0293(10) 0.0544(13) -0.0041(9) -0.0095(9) -0.0015(8) N21 0.0299(10) 0.0280(10) 0.0432(11) -0.0053(8) -0.0071(8) 0.0009(8) N22 0.0310(10) 0.0283(10) 0.0452(12) -0.0067(8) -0.0064(8) 0.0031(8) N23 0.0357(11) 0.0301(10) 0.0442(12) -0.0016(9) -0.0088(9) 0.0059(8) N24 0.0315(10) 0.0305(10) 0.0429(12) -0.0043(8) -0.0054(8) 0.0072(8) C41 0.065(2) 0.0482(17) 0.073(2) -0.0090(16) 0.0028(17) -0.0025(15) C42 0.088(2) 0.0382(15) 0.0522(18) -0.0055(13) -0.0020(17) 0.0081(15) C43 0.067(2) 0.0521(18) 0.070(2) -0.0179(16) -0.0135(17) 0.0118(16) C31 0.109(4) 0.121(5) 0.186(6) -0.075(4) -0.054(4) 0.023(4) C32 0.128(5) 0.125(5) 0.101(4) -0.013(3) -0.033(3) 0.048(4) C33 0.137(5) 0.078(3) 0.175(6) -0.018(4) -0.039(4) 0.009(3) F1 0.0747(15) 0.0648(14) 0.0672(15) -0.0266(11) -0.0113(11) 0.0001(11) F1A 0.0747(15) 0.0648(14) 0.0672(15) -0.0266(11) -0.0113(11) 0.0001(11) F2 0.088(2) 0.0655(18) 0.0439(14) -0.0165(12) -0.0082(12) 0.0080(13) F2A 0.088(2) 0.0655(18) 0.0439(14) -0.0165(12) -0.0082(12) 0.0080(13) _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 C1 N12 1.341(3) . ? C1 N13 1.361(3) . ? C1 N14 1.365(3) . ? C11 N11 1.324(3) . ? C11 C12 1.451(4) . ? C11 C113 1.463(4) . ? C12 C13 1.382(4) . ? C12 C17 1.425(4) . ? C13 C14 1.368(5) . ? C14 F1A 1.253(12) . ? C14 C15 1.383(5) . ? C15 C16 1.380(5) . ? C16 C17 1.374(4) . ? C17 C18 1.456(4) . ? C18 C19 1.397(4) . ? C18 C113 1.424(3) . ? C19 C110 1.375(4) . ? C110 C111 1.416(4) . ? C111 F1 1.320(4) . ? C111 C112 1.361(4) . ? C112 C113 1.374(4) . ? C114 C115 1.326(4) . ? C114 N13 1.392(3) . ? C115 N14 1.402(3) . ? 116 117 1.388(4) . ? 116 121 1.388(4) . ? 116 N13 1.437(3) . ? 117 118 1.389(5) . ? 117 122 1.505(5) . ? 118 119 1.374(5) . ? 119 120 1.387(5) . ? 119 123 1.520(5) . ? 120 121 1.391(4) . ? 121 124 1.498(4) . ? 125 130 1.391(3) . ? 125 126 1.391(4) . ? 125 N14 1.441(3) . ? 126 127 1.385(4) . ? 126 131 1.507(4) . ? 127 128 1.391(4) . ? 128 129 1.387(4) . ? 128 132 1.511(4) . ? 129 130 1.383(4) . ? 130 133 1.504(4) . ? C2 N22 1.337(3) . ? C2 N23 1.367(3) . ? C2 N24 1.370(3) . ? C21 N21 1.308(3) . ? C21 C22 1.459(3) . ? C21 C213 1.477(3) . ? C22 C23 1.379(4) . ? C22 C27 1.419(3) . ? C23 C24 1.377(4) . ? C24 F2 1.316(5) . ? C24 C25 1.385(4) . ? C25 C26 1.381(4) . ? C26 C27 1.384(4) . ? C27 C28 1.457(4) . ? C28 C29 1.391(4) . ? C28 C213 1.416(3) . ? C29 C210 1.372(4) . ? C210 C211 1.390(5) . ? C211 F2A 1.225(6) . ? C211 C212 1.389(4) . ? C212 C213 1.375(4) . ? C214 C215 1.320(4) . ? C214 N24 1.396(3) . ? C215 N23 1.404(3) . ? 216 221 1.392(3) . ? 216 217 1.395(3) . ? 216 N24 1.430(3) . ? 217 218 1.383(4) . ? 217 222 1.507(4) . ? 218 219 1.387(4) . ? 219 220 1.383(4) . ? 219 223 1.509(4) . ? 220 221 1.388(4) . ? 221 224 1.508(4) . ? 225 226 1.389(3) . ? 225 230 1.389(4) . ? 225 N23 1.440(3) . ? 226 227 1.385(4) . ? 226 231 1.503(4) . ? 227 228 1.384(4) . ? 228 229 1.384(4) . ? 228 232 1.512(4) . ? 229 230 1.386(4) . ? 230 233 1.511(4) . ? N11 N12 1.336(3) . ? N21 N22 1.358(3) . ? C41 C42 1.365(5) . ? C41 C43 1.378(5) 2_575 ? C42 C43 1.375(5) . ? C43 C41 1.378(5) 2_575 ? C31 C32 1.337(8) . ? C31 C33 1.368(8) 2_666 ? C32 C33 1.355(8) . ? C33 C31 1.368(8) 2_666 ? 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 N12 C1 N13 118.9(2) . . ? N12 C1 N14 134.6(2) . . ? N13 C1 N14 106.5(2) . . ? N11 C11 C12 120.8(2) . . ? N11 C11 C113 131.1(2) . . ? C12 C11 C113 107.9(2) . . ? C13 C12 C17 119.9(3) . . ? C13 C12 C11 132.3(3) . . ? C17 C12 C11 107.7(2) . . ? C14 C13 C12 119.8(3) . . ? F1A C14 C13 117.3(6) . . ? F1A C14 C15 122.0(5) . . ? C13 C14 C15 120.4(4) . . ? C16 C15 C14 121.0(3) . . ? C17 C16 C15 119.7(3) . . ? C16 C17 C12 119.2(3) . . ? C16 C17 C18 132.4(3) . . ? C12 C17 C18 108.4(2) . . ? C19 C18 C113 120.5(3) . . ? C19 C18 C17 131.0(2) . . ? C113 C18 C17 108.5(2) . . ? C110 C19 C18 119.8(3) . . ? C19 C110 C111 118.4(3) . . ? F1 C111 C112 120.0(3) . . ? F1 C111 C110 117.4(3) . . ? C112 C111 C110 122.6(3) . . ? C111 C112 C113 119.7(3) . . ? C112 C113 C18 119.1(2) . . ? C112 C113 C11 133.5(2) . . ? C18 C113 C11 107.4(2) . . ? C115 C114 N13 107.8(2) . . ? C114 C115 N14 108.0(2) . . ? 117 116 121 122.7(3) . . ? 117 116 N13 118.5(3) . . ? 121 116 N13 118.7(2) . . ? 116 117 118 117.4(3) . . ? 116 117 122 120.7(3) . . ? 118 117 122 121.9(3) . . ? 119 118 117 122.2(3) . . ? 118 119 120 118.6(3) . . ? 118 119 123 121.2(4) . . ? 120 119 123 120.2(4) . . ? 119 120 121 121.8(3) . . ? 116 121 120 117.4(3) . . ? 116 121 124 121.4(3) . . ? 120 121 124 121.2(3) . . ? 130 125 126 122.3(3) . . ? 130 125 N14 118.0(2) . . ? 126 125 N14 119.6(2) . . ? 127 126 125 117.6(2) . . ? 127 126 131 121.4(2) . . ? 125 126 131 121.0(3) . . ? 126 127 128 122.3(3) . . ? 129 128 127 117.7(3) . . ? 129 128 132 121.0(3) . . ? 127 128 132 121.4(3) . . ? 130 129 128 122.5(2) . . ? 129 130 125 117.5(2) . . ? 129 130 133 121.1(2) . . ? 125 130 133 121.4(2) . . ? N22 C2 N23 133.1(2) . . ? N22 C2 N24 120.6(2) . . ? N23 C2 N24 106.26(19) . . ? N21 C21 C22 120.7(2) . . ? N21 C21 C213 132.2(2) . . ? C22 C21 C213 107.1(2) . . ? C23 C22 C27 120.1(2) . . ? C23 C22 C21 131.4(2) . . ? C27 C22 C21 108.5(2) . . ? C24 C23 C22 118.1(3) . . ? F2 C24 C23 119.2(3) . . ? F2 C24 C25 117.9(3) . . ? C23 C24 C25 122.8(3) . . ? C26 C25 C24 119.2(3) . . ? C25 C26 C27 119.6(3) . . ? C26 C27 C22 120.1(3) . . ? C26 C27 C28 132.1(2) . . ? C22 C27 C28 107.8(2) . . ? C29 C28 C213 119.9(3) . . ? C29 C28 C27 130.6(2) . . ? C213 C28 C27 109.4(2) . . ? C210 C29 C28 119.3(3) . . ? C29 C210 C211 120.4(3) . . ? F2A C211 C212 119.6(4) . . ? F2A C211 C210 118.8(4) . . ? C212 C211 C210 121.3(3) . . ? C213 C212 C211 118.7(3) . . ? C212 C213 C28 120.3(2) . . ? C212 C213 C21 132.6(2) . . ? C28 C213 C21 107.1(2) . . ? C215 C214 N24 107.9(2) . . ? C214 C215 N23 108.3(2) . . ? 221 216 217 121.6(2) . . ? 221 216 N24 118.5(2) . . ? 217 216 N24 119.8(2) . . ? 218 217 216 118.0(2) . . ? 218 217 222 120.7(2) . . ? 216 217 222 121.3(2) . . ? 217 218 219 122.3(3) . . ? 220 219 218 117.9(3) . . ? 220 219 223 121.3(3) . . ? 218 219 223 120.8(3) . . ? 219 220 221 122.2(3) . . ? 220 221 216 118.0(2) . . ? 220 221 224 120.5(2) . . ? 216 221 224 121.5(2) . . ? 226 225 230 122.8(2) . . ? 226 225 N23 118.3(2) . . ? 230 225 N23 119.0(2) . . ? 227 226 225 117.4(3) . . ? 227 226 231 121.5(3) . . ? 225 226 231 121.0(3) . . ? 228 227 226 122.0(3) . . ? 229 228 227 118.5(3) . . ? 229 228 232 120.5(3) . . ? 227 228 232 121.0(3) . . ? 228 229 230 122.1(3) . . ? 229 230 225 117.3(2) . . ? 229 230 233 122.1(3) . . ? 225 230 233 120.5(2) . . ? C11 N11 N12 114.0(2) . . ? N11 N12 C1 111.5(2) . . ? C1 N13 C114 109.2(2) . . ? C1 N13 116 122.2(2) . . ? C114 N13 116 128.3(2) . . ? C1 N14 C115 108.5(2) . . ? C1 N14 125 125.4(2) . . ? C115 N14 125 124.8(2) . . ? C21 N21 N22 115.6(2) . . ? C2 N22 N21 111.40(19) . . ? C2 N23 C215 108.5(2) . . ? C2 N23 225 127.56(19) . . ? C215 N23 225 123.3(2) . . ? C2 N24 C214 109.0(2) . . ? C2 N24 216 125.94(19) . . ? C214 N24 216 125.0(2) . . ? C42 C41 C43 120.0(3) . 2_575 ? C41 C42 C43 120.2(3) . . ? C42 C43 C41 119.8(3) . 2_575 ? C32 C31 C33 120.4(5) . 2_666 ? C31 C32 C33 120.1(5) . . ? C32 C33 C31 119.4(5) . 2_666 ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.692 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.058 data_jcc10 _database_code_depnum_ccdc_archive 'CCDC 236038' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 N4' _chemical_formula_weight 496.64 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' _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 9.7936(6) _cell_length_b 10.0529(7) _cell_length_c 16.2514(10) _cell_angle_alpha 75.7650(10) _cell_angle_beta 79.7110(10) _cell_angle_gamma 64.3210(10) _cell_volume 1392.95(16) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max .3 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 6990 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4634 _reflns_number_gt 3619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0858P)^2^+0.4728P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4634 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1622 _refine_ls_wR_factor_gt 0.1485 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.011 _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 N1 N 0.6926(2) 0.8679(2) 0.12256(11) 0.0477(5) Uani 1 1 d . . . N2 N 0.6680(2) 0.8578(2) 0.25981(11) 0.0445(4) Uani 1 1 d . . . N3 N 0.9226(2) 0.7883(2) 0.18405(10) 0.0437(4) Uani 1 1 d . . . N4 N 0.9681(2) 0.8036(2) 0.25477(10) 0.0414(4) Uani 1 1 d . . . C1 C 0.5389(3) 0.9087(3) 0.14957(15) 0.0581(7) Uani 1 1 d . . . H2B H 0.4602 0.9358 0.1150 0.070 Uiso 1 1 calc R . . C2 C 0.5241(3) 0.9025(3) 0.23330(15) 0.0552(6) Uani 1 1 d . . . H3A H 0.4327 0.9243 0.2684 0.066 Uiso 1 1 calc R . . C3 C 0.7727(2) 0.8363(2) 0.19079(13) 0.0410(5) Uani 1 1 d . . . C11 C 0.7602(3) 0.8594(3) 0.03669(13) 0.0463(5) Uani 1 1 d . . . C12 C 0.7927(3) 0.9780(3) -0.01150(14) 0.0485(6) Uani 1 1 d . . . C13 C 0.8596(3) 0.9655(3) -0.09360(15) 0.0551(6) Uani 1 1 d . . . H13A H 0.8824 1.0448 -0.1274 0.066 Uiso 1 1 calc R . . C14 C 0.8938(3) 0.8398(3) -0.12728(15) 0.0598(7) Uani 1 1 d . . . C15 C 0.8584(4) 0.7245(3) -0.07672(16) 0.0673(8) Uani 1 1 d . . . H15A H 0.8794 0.6394 -0.0993 0.081 Uiso 1 1 calc R . . C16 C 0.7933(3) 0.7304(3) 0.00587(15) 0.0584(7) Uani 1 1 d . . . C17 C 0.7574(4) 1.1155(3) 0.02376(18) 0.0734(8) Uani 1 1 d . . . H17A H 0.7876 1.1860 -0.0191 0.110 Uiso 1 1 calc R . . H17B H 0.8126 1.0867 0.0737 0.110 Uiso 1 1 calc R . . H17C H 0.6491 1.1623 0.0394 0.110 Uiso 1 1 calc R . . C18 C 0.9687(4) 0.8282(4) -0.21668(18) 0.0903(10) Uani 1 1 d . . . H18A H 0.9832 0.7335 -0.2295 0.136 Uiso 1 1 calc R . . H18B H 1.0665 0.8332 -0.2208 0.136 Uiso 1 1 calc R . . H18C H 0.9044 0.9107 -0.2570 0.136 Uiso 1 1 calc R . . C19 C 0.7587(5) 0.6023(4) 0.06144(19) 0.0914(11) Uani 1 1 d . . . H19A H 0.7887 0.5223 0.0299 0.137 Uiso 1 1 calc R . . H19B H 0.6505 0.6380 0.0783 0.137 Uiso 1 1 calc R . . H19C H 0.8145 0.5645 0.1118 0.137 Uiso 1 1 calc R . . C21 C 0.7011(2) 0.8125(2) 0.34796(13) 0.0408(5) Uani 1 1 d . . . C22 C 0.7637(2) 0.6600(2) 0.38272(13) 0.0431(5) Uani 1 1 d . . . C23 C 0.7948(2) 0.6182(3) 0.46759(14) 0.0473(5) Uani 1 1 d . . . H23A H 0.8372 0.5155 0.4923 0.057 Uiso 1 1 calc R . . C24 C 0.7650(2) 0.7239(3) 0.51696(13) 0.0470(5) Uani 1 1 d . . . C25 C 0.7016(3) 0.8755(3) 0.47950(13) 0.0483(6) Uani 1 1 d . . . H25A H 0.6797 0.9481 0.5126 0.058 Uiso 1 1 calc R . . C26 C 0.6698(2) 0.9226(3) 0.39474(13) 0.0450(5) Uani 1 1 d . . . C27 C 0.8036(3) 0.5436(3) 0.32883(16) 0.0561(6) Uani 1 1 d . . . H27A H 0.7745 0.5933 0.2715 0.084 Uiso 1 1 calc R . . H27B H 0.7497 0.4798 0.3534 0.084 Uiso 1 1 calc R . . H27C H 0.9122 0.4827 0.3269 0.084 Uiso 1 1 calc R . . C28 C 0.8052(3) 0.6756(3) 0.60814(15) 0.0654(7) Uani 1 1 d . . . H28A H 0.8476 0.5667 0.6234 0.098 Uiso 1 1 calc R . . H28B H 0.7144 0.7174 0.6453 0.098 Uiso 1 1 calc R . . H28C H 0.8794 0.7116 0.6143 0.098 Uiso 1 1 calc R . . C29 C 0.6166(3) 1.0854(3) 0.35262(16) 0.0628(7) Uani 1 1 d . . . H29A H 0.6008 1.1456 0.3946 0.094 Uiso 1 1 calc R . . H29B H 0.5218 1.1170 0.3278 0.094 Uiso 1 1 calc R . . H29C H 0.6927 1.0987 0.3082 0.094 Uiso 1 1 calc R . . C30 C 1.1121(2) 0.7296(2) 0.26731(12) 0.0385(5) Uani 1 1 d . . . C31 C 1.1716(2) 0.7428(2) 0.34039(13) 0.0397(5) Uani 1 1 d . . . C32 C 1.1004(3) 0.8284(3) 0.40308(14) 0.0493(6) Uani 1 1 d . . . H32A H 0.9964 0.8923 0.4027 0.059 Uiso 1 1 calc R . . C33 C 1.1838(3) 0.8185(3) 0.46587(16) 0.0571(6) Uani 1 1 d . . . H33A H 1.1365 0.8765 0.5084 0.069 Uiso 1 1 calc R . . C34 C 1.3371(3) 0.7236(3) 0.46681(15) 0.0566(6) Uani 1 1 d . . . H34A H 1.3926 0.7189 0.5098 0.068 Uiso 1 1 calc R . . C35 C 1.4095(3) 0.6357(3) 0.40541(14) 0.0499(6) Uani 1 1 d . . . H35A H 1.5129 0.5702 0.4071 0.060 Uiso 1 1 calc R . . C36 C 1.3268(2) 0.6460(2) 0.34119(13) 0.0398(5) Uani 1 1 d . . . C37 C 1.3701(2) 0.5695(2) 0.26841(13) 0.0408(5) Uani 1 1 d . . . C38 C 1.5077(3) 0.4617(3) 0.24261(15) 0.0496(6) Uani 1 1 d . . . H38A H 1.5935 0.4272 0.2731 0.059 Uiso 1 1 calc R . . C39 C 1.5164(3) 0.4057(3) 0.17134(16) 0.0579(6) Uani 1 1 d . . . H39A H 1.6093 0.3334 0.1528 0.069 Uiso 1 1 calc R . . C40 C 1.3893(3) 0.4553(3) 0.12674(16) 0.0577(6) Uani 1 1 d . . . H40A H 1.3974 0.4154 0.0786 0.069 Uiso 1 1 calc R . . C41 C 1.2507(3) 0.5627(3) 0.15197(14) 0.0493(6) Uani 1 1 d . . . H41A H 1.1653 0.5955 0.1214 0.059 Uiso 1 1 calc R . . C42 C 1.2403(2) 0.6208(2) 0.22326(13) 0.0399(5) 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 N1 0.0436(10) 0.0680(12) 0.0353(10) -0.0074(8) -0.0099(8) -0.0251(9) N2 0.0419(10) 0.0556(11) 0.0357(9) -0.0057(8) -0.0084(8) -0.0194(9) N3 0.0443(10) 0.0553(11) 0.0354(9) -0.0069(8) -0.0101(8) -0.0222(9) N4 0.0458(11) 0.0490(10) 0.0334(9) -0.0057(8) -0.0075(7) -0.0225(9) C1 0.0439(14) 0.0834(18) 0.0491(14) -0.0059(12) -0.0150(11) -0.0272(13) C2 0.0382(12) 0.0750(17) 0.0486(14) -0.0063(12) -0.0097(10) -0.0201(11) C3 0.0425(12) 0.0476(12) 0.0344(11) -0.0053(9) -0.0088(9) -0.0190(10) C11 0.0479(13) 0.0613(14) 0.0352(11) -0.0058(10) -0.0115(9) -0.0261(11) C12 0.0498(13) 0.0520(13) 0.0449(13) -0.0072(10) -0.0115(10) -0.0201(11) C13 0.0621(15) 0.0579(15) 0.0454(13) -0.0005(11) -0.0051(11) -0.0293(12) C14 0.0673(17) 0.0738(17) 0.0428(13) -0.0128(12) -0.0027(11) -0.0328(14) C15 0.098(2) 0.0729(18) 0.0482(14) -0.0210(13) -0.0026(14) -0.0467(17) C16 0.0816(18) 0.0674(16) 0.0446(13) -0.0086(12) -0.0095(12) -0.0468(15) C17 0.097(2) 0.0583(17) 0.0651(18) -0.0132(13) -0.0064(15) -0.0315(16) C18 0.117(3) 0.105(3) 0.0529(17) -0.0227(17) 0.0156(17) -0.053(2) C19 0.151(3) 0.090(2) 0.0641(19) -0.0103(16) -0.0036(19) -0.082(2) C21 0.0369(11) 0.0519(13) 0.0338(11) -0.0049(9) -0.0064(8) -0.0187(10) C22 0.0391(11) 0.0495(13) 0.0440(12) -0.0068(10) -0.0076(9) -0.0204(10) C23 0.0448(12) 0.0487(13) 0.0468(13) 0.0015(10) -0.0090(10) -0.0213(10) C24 0.0440(12) 0.0631(15) 0.0358(11) -0.0019(10) -0.0041(9) -0.0271(11) C25 0.0529(13) 0.0612(15) 0.0368(12) -0.0147(10) 0.0031(10) -0.0284(12) C26 0.0437(12) 0.0504(13) 0.0384(12) -0.0077(10) 0.0002(9) -0.0188(10) C27 0.0606(15) 0.0519(14) 0.0607(15) -0.0121(11) -0.0109(12) -0.0245(12) C28 0.0653(17) 0.089(2) 0.0396(13) -0.0009(13) -0.0107(12) -0.0333(15) C29 0.0777(18) 0.0501(14) 0.0520(15) -0.0083(11) 0.0006(13) -0.0212(13) C30 0.0402(11) 0.0429(11) 0.0357(11) -0.0050(9) -0.0067(9) -0.0199(9) C31 0.0417(12) 0.0437(12) 0.0378(11) -0.0048(9) -0.0073(9) -0.0214(10) C32 0.0459(13) 0.0551(14) 0.0471(13) -0.0168(11) -0.0053(10) -0.0166(11) C33 0.0611(16) 0.0619(15) 0.0525(14) -0.0237(12) -0.0090(12) -0.0205(13) C34 0.0616(16) 0.0651(16) 0.0514(14) -0.0178(12) -0.0184(12) -0.0248(13) C35 0.0434(12) 0.0553(14) 0.0544(14) -0.0119(11) -0.0135(10) -0.0189(11) C36 0.0416(12) 0.0402(11) 0.0417(11) -0.0057(9) -0.0074(9) -0.0201(9) C37 0.0443(12) 0.0393(11) 0.0428(12) -0.0048(9) -0.0059(9) -0.0215(10) C38 0.0445(13) 0.0462(13) 0.0608(15) -0.0139(11) -0.0068(11) -0.0181(10) C39 0.0568(15) 0.0515(14) 0.0660(16) -0.0238(12) 0.0007(12) -0.0182(12) C40 0.0676(17) 0.0596(15) 0.0520(14) -0.0245(12) -0.0029(12) -0.0248(13) C41 0.0572(14) 0.0504(13) 0.0436(12) -0.0104(10) -0.0092(10) -0.0224(11) C42 0.0464(12) 0.0414(11) 0.0364(11) -0.0042(9) -0.0053(9) -0.0232(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 N1 C3 1.366(3) . ? N1 C1 1.394(3) . ? N1 C11 1.440(3) . ? N2 C3 1.368(3) . ? N2 C2 1.395(3) . ? N2 C21 1.443(3) . ? N3 C3 1.325(3) . ? N3 N4 1.369(2) . ? N4 C30 1.304(3) . ? C1 C2 1.331(3) . ? C11 C12 1.385(3) . ? C11 C16 1.391(3) . ? C12 C13 1.387(3) . ? C12 C17 1.504(3) . ? C13 C14 1.384(4) . ? C14 C15 1.384(4) . ? C14 C18 1.514(3) . ? C15 C16 1.383(3) . ? C16 C19 1.511(4) . ? C21 C22 1.388(3) . ? C21 C26 1.390(3) . ? C22 C23 1.388(3) . ? C22 C27 1.509(3) . ? C23 C24 1.388(3) . ? C24 C25 1.392(3) . ? C24 C28 1.508(3) . ? C25 C26 1.387(3) . ? C26 C29 1.502(3) . ? C30 C42 1.470(3) . ? C30 C31 1.470(3) . ? C31 C32 1.387(3) . ? C31 C36 1.405(3) . ? C32 C33 1.377(3) . ? C33 C34 1.387(3) . ? C34 C35 1.385(3) . ? C35 C36 1.390(3) . ? C36 C37 1.468(3) . ? C37 C38 1.387(3) . ? C37 C42 1.414(3) . ? C38 C39 1.381(3) . ? C39 C40 1.390(4) . ? C40 C41 1.387(3) . ? C41 C42 1.390(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C1 109.50(18) . . ? C3 N1 C11 124.02(18) . . ? C1 N1 C11 126.48(18) . . ? C3 N2 C2 109.10(17) . . ? C3 N2 C21 126.05(17) . . ? C2 N2 C21 123.67(18) . . ? C3 N3 N4 109.73(17) . . ? C30 N4 N3 116.71(17) . . ? C2 C1 N1 107.5(2) . . ? C1 C2 N2 108.0(2) . . ? N3 C3 N1 122.38(19) . . ? N3 C3 N2 131.67(19) . . ? N1 C3 N2 105.88(18) . . ? C12 C11 C16 122.5(2) . . ? C12 C11 N1 119.0(2) . . ? C16 C11 N1 118.5(2) . . ? C11 C12 C13 117.6(2) . . ? C11 C12 C17 121.4(2) . . ? C13 C12 C17 121.1(2) . . ? C14 C13 C12 122.1(2) . . ? C13 C14 C15 118.1(2) . . ? C13 C14 C18 121.0(2) . . ? C15 C14 C18 120.9(2) . . ? C16 C15 C14 122.2(2) . . ? C15 C16 C11 117.5(2) . . ? C15 C16 C19 121.9(2) . . ? C11 C16 C19 120.6(2) . . ? C22 C21 C26 122.50(19) . . ? C22 C21 N2 118.52(19) . . ? C26 C21 N2 119.0(2) . . ? C23 C22 C21 117.9(2) . . ? C23 C22 C27 121.1(2) . . ? C21 C22 C27 121.0(2) . . ? C22 C23 C24 121.7(2) . . ? C23 C24 C25 118.4(2) . . ? C23 C24 C28 120.8(2) . . ? C25 C24 C28 120.8(2) . . ? C26 C25 C24 121.9(2) . . ? C25 C26 C21 117.6(2) . . ? C25 C26 C29 121.4(2) . . ? C21 C26 C29 120.8(2) . . ? N4 C30 C42 132.96(18) . . ? N4 C30 C31 120.35(18) . . ? C42 C30 C31 106.62(17) . . ? C32 C31 C36 120.52(19) . . ? C32 C31 C30 131.0(2) . . ? C36 C31 C30 108.47(17) . . ? C33 C32 C31 119.2(2) . . ? C32 C33 C34 120.5(2) . . ? C33 C34 C35 121.0(2) . . ? C34 C35 C36 118.9(2) . . ? C35 C36 C31 119.79(19) . . ? C35 C36 C37 131.8(2) . . ? C31 C36 C37 108.44(18) . . ? C38 C37 C42 120.8(2) . . ? C38 C37 C36 130.8(2) . . ? C42 C37 C36 108.33(18) . . ? C39 C38 C37 118.8(2) . . ? C38 C39 C40 120.7(2) . . ? C41 C40 C39 121.2(2) . . ? C40 C41 C42 118.8(2) . . ? C41 C42 C37 119.7(2) . . ? C41 C42 C30 132.2(2) . . ? C37 C42 C30 108.13(17) . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.382 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.038 data_pbca _database_code_depnum_ccdc_archive 'CCDC 236039' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 N4' _chemical_formula_weight 372.50 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0490(6) _cell_length_b 18.8681(10) _cell_length_c 19.8287(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4133.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4646 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 23.07 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 '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 38365 _diffrn_reflns_av_R_equivalents 0.1136 _diffrn_reflns_av_sigmaI/netI 0.0678 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.54 _reflns_number_total 4770 _reflns_number_gt 2656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0609P)^2^+0.9434P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4770 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1237 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 C1 C 1.07957(19) 0.10535(11) 0.09142(11) 0.0310(5) Uani 1 1 d . . . C3 C 1.22408(18) 0.02902(11) 0.05790(10) 0.0310(5) Uani 1 1 d . . . C4 C 1.26494(19) 0.09459(12) 0.04598(11) 0.0341(5) Uani 1 1 d . . . C11 C 0.78430(19) 0.12808(11) 0.14255(11) 0.0321(5) Uani 1 1 d . . . C12 C 0.76128(19) 0.20048(12) 0.16674(11) 0.0332(5) Uani 1 1 d . . . C13 C 0.8315(2) 0.26176(12) 0.16640(12) 0.0377(6) Uani 1 1 d . . . H13 H 0.911(2) 0.26101(12) 0.1491(5) 0.045 Uiso 1 1 calc R . . C14 C 0.7825(2) 0.32410(14) 0.19201(12) 0.0453(6) Uani 1 1 d . . . H14 H 0.8334(13) 0.3694(12) 0.19221(12) 0.054 Uiso 1 1 calc R . . C15 C 0.6657(2) 0.32568(14) 0.21724(13) 0.0494(7) Uani 1 1 d . . . H15 H 0.6337(9) 0.3694(12) 0.2349(5) 0.059 Uiso 1 1 calc R . . C16 C 0.5946(2) 0.26560(14) 0.21744(13) 0.0474(7) Uani 1 1 d . . . H16 H 0.516(2) 0.26717(14) 0.2342(5) 0.057 Uiso 1 1 calc R . . C17 C 0.64186(19) 0.20297(12) 0.19242(11) 0.0359(5) Uani 1 1 d . . . C18 C 0.5871(2) 0.13262(13) 0.18482(11) 0.0375(6) Uani 1 1 d . . . C19 C 0.4741(2) 0.10657(15) 0.20315(12) 0.0450(6) Uani 1 1 d . . . H19 H 0.4172(16) 0.1360(8) 0.2256(6) 0.054 Uiso 1 1 calc R . . C21 C 1.0436(2) -0.02216(11) 0.12431(11) 0.0319(5) Uani 1 1 d . . . H21 H 0.9751(17) 0.0004(6) 0.1471(6) 0.038 Uiso 1 1 calc R . . C22 C 1.1224(2) -0.05411(13) 0.17905(12) 0.0411(6) Uani 1 1 d . . . H22A H 1.1914 -0.0784 0.1584 0.062 Uiso 1 1 calc R . . H22B H 1.0748 -0.0882 0.2053 0.062 Uiso 1 1 calc R . . H22C H 1.1518 -0.0164 0.2088 0.062 Uiso 1 1 calc R . . C23 C 0.9907(2) -0.07648(13) 0.07636(13) 0.0484(7) Uani 1 1 d . . . H23A H 0.9352 -0.0530 0.0450 0.073 Uiso 1 1 calc R . . H23B H 0.9466 -0.1125 0.1021 0.073 Uiso 1 1 calc R . . H23C H 1.0562 -0.0991 0.0509 0.073 Uiso 1 1 calc R . . C31 C 1.2808(2) -0.04000(12) 0.03825(12) 0.0406(6) Uani 1 1 d . . . H31A H 1.3584 -0.0310 0.0159 0.061 Uiso 1 1 calc R . . H31B H 1.2269 -0.0654 0.0073 0.061 Uiso 1 1 calc R . . H31C H 1.2942 -0.0688 0.0787 0.061 Uiso 1 1 calc R . . C41 C 1.3826(2) 0.11642(14) 0.01525(13) 0.0474(6) Uani 1 1 d . . . H41A H 1.4259 0.0743 -0.0007 0.071 Uiso 1 1 calc R . . H41B H 1.4318 0.1409 0.0491 0.071 Uiso 1 1 calc R . . H41C H 1.3673 0.1483 -0.0228 0.071 Uiso 1 1 calc R . . C51 C 1.1776(2) 0.22049(12) 0.06607(14) 0.0485(7) Uani 1 1 d . . . H51 H 1.095(2) 0.2338(4) 0.0877(6) 0.058 Uiso 1 1 calc R . . C52 C 1.2662(4) 0.25016(16) 0.11418(18) 0.0933(13) Uani 1 1 d . . . H52A H 1.3482 0.2442 0.0961 0.140 Uiso 1 1 calc R . . H52B H 1.2596 0.2253 0.1574 0.140 Uiso 1 1 calc R . . H52C H 1.2497 0.3007 0.1209 0.140 Uiso 1 1 calc R . . C53 C 1.1688(4) 0.25085(16) -0.00166(17) 0.1000(15) Uani 1 1 d . . . H53A H 1.2413 0.2385 -0.0276 0.150 Uiso 1 1 calc R . . H53B H 1.1622 0.3025 0.0016 0.150 Uiso 1 1 calc R . . H53C H 1.0970 0.2319 -0.0244 0.150 Uiso 1 1 calc R . . C110 C 0.4463(2) 0.03697(15) 0.18809(13) 0.0492(7) Uani 1 1 d . . . H110 H 0.368(2) 0.0184(5) 0.2003(4) 0.059 Uiso 1 1 calc R . . C111 C 0.5293(2) -0.00684(15) 0.15551(13) 0.0457(6) Uani 1 1 d . . . H111 H 0.5062(6) -0.0569(13) 0.1441(3) 0.055 Uiso 1 1 calc R . . C112 C 0.6432(2) 0.01808(13) 0.13876(12) 0.0388(6) Uani 1 1 d . . . H112 H 0.7021(15) -0.0130(8) 0.1171(6) 0.047 Uiso 1 1 calc R . . C113 C 0.67254(19) 0.08823(12) 0.15329(11) 0.0331(5) Uani 1 1 d . . . N2 N 1.10855(15) 0.03489(9) 0.08761(9) 0.0294(4) Uani 1 1 d . . . N5 N 1.17604(16) 0.14203(9) 0.06718(10) 0.0352(5) Uani 1 1 d . . . N11 N 0.98064(16) 0.13988(10) 0.11275(9) 0.0342(4) Uani 1 1 d . . . N12 N 0.88140(16) 0.09816(9) 0.11757(9) 0.0331(4) 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 C1 0.0284(12) 0.0289(12) 0.0358(12) -0.0026(10) -0.0027(10) -0.0004(9) C3 0.0262(11) 0.0370(12) 0.0298(12) 0.0013(10) 0.0000(9) 0.0014(9) C4 0.0267(12) 0.0395(13) 0.0362(13) 0.0022(10) 0.0007(10) -0.0012(10) C11 0.0291(12) 0.0355(13) 0.0318(12) -0.0002(10) -0.0023(9) 0.0046(10) C12 0.0310(12) 0.0393(13) 0.0292(12) -0.0026(10) -0.0050(10) 0.0062(10) C13 0.0353(13) 0.0405(14) 0.0375(13) -0.0029(11) -0.0056(10) 0.0027(11) C14 0.0492(15) 0.0418(14) 0.0448(15) -0.0076(12) -0.0124(12) 0.0056(12) C15 0.0491(16) 0.0476(16) 0.0517(16) -0.0154(13) -0.0090(13) 0.0191(13) C16 0.0406(15) 0.0578(17) 0.0439(15) -0.0072(12) 0.0003(12) 0.0132(13) C17 0.0289(12) 0.0463(14) 0.0325(13) -0.0030(10) -0.0036(10) 0.0070(10) C18 0.0317(12) 0.0508(15) 0.0301(12) 0.0015(10) -0.0024(10) 0.0046(11) C19 0.0298(13) 0.0659(18) 0.0393(14) 0.0022(13) 0.0005(11) 0.0043(12) C21 0.0294(11) 0.0313(12) 0.0348(12) 0.0036(10) 0.0001(9) -0.0021(10) C22 0.0401(13) 0.0472(14) 0.0361(13) 0.0066(11) 0.0019(11) -0.0032(11) C23 0.0520(16) 0.0511(16) 0.0422(15) 0.0031(12) -0.0076(12) -0.0185(13) C31 0.0343(13) 0.0440(14) 0.0435(14) -0.0029(11) 0.0027(11) 0.0071(11) C41 0.0365(14) 0.0528(15) 0.0528(16) 0.0027(12) 0.0088(12) -0.0051(12) C51 0.0471(16) 0.0311(13) 0.0673(19) 0.0029(12) -0.0014(13) -0.0075(11) C52 0.158(4) 0.0432(18) 0.079(2) -0.0150(16) -0.025(2) -0.011(2) C53 0.198(5) 0.0399(16) 0.062(2) 0.0074(15) -0.024(3) 0.011(2) C110 0.0300(13) 0.0698(19) 0.0478(16) 0.0133(14) -0.0021(11) -0.0090(13) C111 0.0374(14) 0.0508(16) 0.0489(16) 0.0078(12) -0.0091(11) -0.0076(12) C112 0.0337(13) 0.0420(14) 0.0406(13) 0.0025(11) -0.0029(10) -0.0009(11) C113 0.0286(12) 0.0408(13) 0.0300(12) 0.0014(10) -0.0031(9) 0.0027(10) N2 0.0243(9) 0.0299(10) 0.0341(10) 0.0006(8) 0.0022(8) 0.0007(8) N5 0.0298(10) 0.0309(10) 0.0448(12) 0.0003(9) 0.0020(8) -0.0026(8) N11 0.0290(10) 0.0327(10) 0.0408(11) -0.0013(8) 0.0004(8) 0.0015(8) N12 0.0283(10) 0.0364(10) 0.0345(10) -0.0008(8) -0.0022(8) 0.0003(8) _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 C1 N11 1.341(3) . ? C1 N5 1.359(3) . ? C1 N2 1.370(3) . ? C3 C4 1.338(3) . ? C3 N2 1.410(3) . ? C3 C31 1.497(3) . ? C4 N5 1.394(3) . ? C4 C41 1.494(3) . ? C11 N12 1.310(3) . ? C11 C113 1.461(3) . ? C11 C12 1.470(3) . ? C12 C13 1.392(3) . ? C12 C17 1.415(3) . ? C13 C14 1.391(3) . ? C14 C15 1.384(4) . ? C15 C16 1.380(4) . ? C16 C17 1.384(3) . ? C17 C18 1.467(3) . ? C18 C19 1.390(3) . ? C18 C113 1.408(3) . ? C19 C110 1.381(4) . ? C21 N2 1.485(3) . ? C21 C23 1.515(3) . ? C21 C22 1.516(3) . ? C51 C53 1.463(4) . ? C51 C52 1.477(4) . ? C51 N5 1.481(3) . ? C110 C111 1.393(4) . ? C111 C112 1.385(3) . ? C112 C113 1.393(3) . ? N11 N12 1.353(2) . ? 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 N11 C1 N5 120.23(19) . . ? N11 C1 N2 132.8(2) . . ? N5 C1 N2 106.95(18) . . ? C4 C3 N2 107.85(18) . . ? C4 C3 C31 128.12(19) . . ? N2 C3 C31 123.78(19) . . ? C3 C4 N5 107.63(18) . . ? C3 C4 C41 128.4(2) . . ? N5 C4 C41 124.0(2) . . ? N12 C11 C113 121.71(19) . . ? N12 C11 C12 131.7(2) . . ? C113 C11 C12 106.52(18) . . ? C13 C12 C17 119.6(2) . . ? C13 C12 C11 132.3(2) . . ? C17 C12 C11 108.0(2) . . ? C14 C13 C12 118.9(2) . . ? C15 C14 C13 120.9(3) . . ? C16 C15 C14 121.0(2) . . ? C15 C16 C17 119.0(2) . . ? C16 C17 C12 120.6(2) . . ? C16 C17 C18 130.8(2) . . ? C12 C17 C18 108.51(19) . . ? C19 C18 C113 120.5(2) . . ? C19 C18 C17 131.6(2) . . ? C113 C18 C17 107.91(19) . . ? C110 C19 C18 118.7(2) . . ? N2 C21 C23 111.67(19) . . ? N2 C21 C22 111.20(17) . . ? C23 C21 C22 113.67(19) . . ? C53 C51 C52 119.3(3) . . ? C53 C51 N5 113.8(2) . . ? C52 C51 N5 112.2(2) . . ? C19 C110 C111 121.2(2) . . ? C112 C111 C110 120.5(3) . . ? C111 C112 C113 119.0(2) . . ? C112 C113 C18 120.1(2) . . ? C112 C113 C11 130.9(2) . . ? C18 C113 C11 109.0(2) . . ? C1 N2 C3 108.11(17) . . ? C1 N2 C21 124.31(17) . . ? C3 N2 C21 125.85(17) . . ? C1 N5 C4 109.41(17) . . ? C1 N5 C51 121.60(19) . . ? C4 N5 C51 128.99(19) . . ? C1 N11 N12 113.59(18) . . ? C11 N12 N11 116.09(18) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.240 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.042 data_p1b_2 _database_code_depnum_ccdc_archive 'CCDC 236040' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H56 N8' _chemical_formula_weight 793.05 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' _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 9.4223(6) _cell_length_b 15.6479(10) _cell_length_c 16.0880(10) _cell_angle_alpha 79.4400(10) _cell_angle_beta 82.2910(10) _cell_angle_gamma 74.5940(10) _cell_volume 2238.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3635 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 23.87 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 '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 22193 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.1075 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.60 _reflns_number_total 10308 _reflns_number_gt 4693 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0702P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10308 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1587 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1357 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _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 C11 C 0.5989(3) 0.20869(16) 0.56565(16) 0.0403(6) Uani 1 1 d . . . C13 C 0.7234(3) 0.20610(18) 0.67551(18) 0.0554(8) Uani 1 1 d . . . H13 H 0.7516 0.2227 0.7222 0.066 Uiso 1 1 calc R . . C14 C 0.7891(3) 0.13285(18) 0.64138(18) 0.0550(8) Uani 1 1 d . . . H14 H 0.8713 0.0889 0.6599 0.066 Uiso 1 1 calc R . . C21 C 0.6743(3) 0.19437(16) 0.07512(17) 0.0396(6) Uani 1 1 d . . . C23 C 0.4974(3) 0.17845(19) 0.18008(17) 0.0512(7) Uani 1 1 d . . . H23 H 0.4057 0.1863 0.2114 0.061 Uiso 1 1 calc R . . C24 C 0.6218(3) 0.12218(19) 0.20453(17) 0.0515(7) Uani 1 1 d . . . H24 H 0.6330 0.0835 0.2558 0.062 Uiso 1 1 calc R . . C121 C 0.5241(3) 0.34355(16) 0.64090(16) 0.0385(6) Uani 1 1 d . . . C122 C 0.3974(3) 0.35496(17) 0.69545(16) 0.0418(6) Uani 1 1 d . . . C123 C 0.3258(3) 0.44219(17) 0.70753(16) 0.0426(7) Uani 1 1 d . . . H123 H 0.2392 0.4521 0.7436 0.051 Uiso 1 1 calc R . . C124 C 0.3795(3) 0.51460(17) 0.66756(17) 0.0435(7) Uani 1 1 d . . . C125 C 0.5079(3) 0.49923(17) 0.61493(17) 0.0452(7) Uani 1 1 d . . . H125 H 0.5447 0.5478 0.5879 0.054 Uiso 1 1 calc R . . C126 C 0.5846(3) 0.41329(18) 0.60084(16) 0.0432(7) Uani 1 1 d . . . C127 C 0.3392(3) 0.27693(18) 0.73954(19) 0.0623(9) Uani 1 1 d . . . H12A H 0.2502 0.2979 0.7745 0.093 Uiso 0.50 1 calc PR . . H12B H 0.4116 0.2367 0.7744 0.093 Uiso 0.50 1 calc PR . . H12C H 0.3182 0.2460 0.6981 0.093 Uiso 0.50 1 calc PR . . H12D H 0.4032 0.2225 0.7235 0.093 Uiso 0.50 1 calc PR . . H12E H 0.2417 0.2837 0.7236 0.093 Uiso 0.50 1 calc PR . . H12F H 0.3352 0.2744 0.7999 0.093 Uiso 0.50 1 calc PR . . C128 C 0.2970(3) 0.60890(17) 0.68043(18) 0.0570(8) Uani 1 1 d . . . H12G H 0.2104 0.6070 0.7190 0.085 Uiso 0.50 1 calc PR . . H12H H 0.2682 0.6435 0.6269 0.085 Uiso 0.50 1 calc PR . . H12I H 0.3598 0.6361 0.7035 0.085 Uiso 0.50 1 calc PR . . H12J H 0.3486 0.6508 0.6473 0.085 Uiso 0.50 1 calc PR . . H12K H 0.2908 0.6142 0.7394 0.085 Uiso 0.50 1 calc PR . . H12L H 0.1991 0.6216 0.6628 0.085 Uiso 0.50 1 calc PR . . C129 C 0.7277(3) 0.3975(2) 0.54576(18) 0.0592(8) Uani 1 1 d . . . H12M H 0.7512 0.4538 0.5236 0.089 Uiso 0.50 1 calc PR . . H12N H 0.7186 0.3687 0.4996 0.089 Uiso 0.50 1 calc PR . . H12O H 0.8050 0.3597 0.5788 0.089 Uiso 0.50 1 calc PR . . H12P H 0.7653 0.3343 0.5444 0.089 Uiso 0.50 1 calc PR . . H12Q H 0.7980 0.4195 0.5684 0.089 Uiso 0.50 1 calc PR . . H12R H 0.7115 0.4284 0.4892 0.089 Uiso 0.50 1 calc PR . . C131 C 0.7468(3) 0.06687(17) 0.51809(16) 0.0412(6) Uani 1 1 d . . . C132 C 0.8317(3) 0.08126(16) 0.44268(17) 0.0435(7) Uani 1 1 d . . . C133 C 0.8570(3) 0.01791(18) 0.38845(17) 0.0463(7) Uani 1 1 d . . . H133 H 0.9125 0.0265 0.3367 0.056 Uiso 1 1 calc R . . C134 C 0.8019(3) -0.05734(19) 0.40947(18) 0.0493(7) Uani 1 1 d . . . C135 C 0.7203(3) -0.06969(19) 0.48610(18) 0.0545(8) Uani 1 1 d . . . H135 H 0.6844 -0.1209 0.5011 0.065 Uiso 1 1 calc R . . C136 C 0.6899(3) -0.00743(19) 0.54208(17) 0.0487(7) Uani 1 1 d . . . C137 C 0.8973(3) 0.16063(18) 0.4200(2) 0.0666(9) Uani 1 1 d . . . H13A H 0.9525 0.1589 0.3654 0.100 Uiso 0.50 1 calc PR . . H13B H 0.9618 0.1592 0.4619 0.100 Uiso 0.50 1 calc PR . . H13C H 0.8196 0.2148 0.4181 0.100 Uiso 0.50 1 calc PR . . H13D H 0.8701 0.1963 0.4649 0.100 Uiso 0.50 1 calc PR . . H13E H 0.8608 0.1961 0.3684 0.100 Uiso 0.50 1 calc PR . . H13F H 1.0030 0.1404 0.4122 0.100 Uiso 0.50 1 calc PR . . C138 C 0.8278(4) -0.1250(2) 0.3497(2) 0.0720(10) Uani 1 1 d . . . H13G H 0.8865 -0.1068 0.2993 0.108 Uiso 0.50 1 calc PR . . H13H H 0.7346 -0.1286 0.3346 0.108 Uiso 0.50 1 calc PR . . H13I H 0.8789 -0.1828 0.3770 0.108 Uiso 0.50 1 calc PR . . H13J H 0.7802 -0.1720 0.3746 0.108 Uiso 0.50 1 calc PR . . H13K H 0.9321 -0.1502 0.3394 0.108 Uiso 0.50 1 calc PR . . H13L H 0.7878 -0.0960 0.2969 0.108 Uiso 0.50 1 calc PR . . C139 C 0.6008(4) -0.0234(2) 0.62564(19) 0.0703(9) Uani 1 1 d . . . H13M H 0.5712 -0.0784 0.6300 0.106 Uiso 0.50 1 calc PR . . H13N H 0.5146 0.0255 0.6291 0.106 Uiso 0.50 1 calc PR . . H13O H 0.6597 -0.0276 0.6712 0.106 Uiso 0.50 1 calc PR . . H13P H 0.5925 0.0247 0.6568 0.106 Uiso 0.50 1 calc PR . . H13Q H 0.6491 -0.0792 0.6578 0.106 Uiso 0.50 1 calc PR . . H13R H 0.5040 -0.0261 0.6156 0.106 Uiso 0.50 1 calc PR . . C141 C 0.2988(3) 0.31583(17) 0.45826(18) 0.0441(7) Uani 1 1 d . . . C142 C 0.1559(3) 0.37781(19) 0.4666(2) 0.0574(8) Uani 1 1 d . . . H142 H 0.1121 0.4017 0.5154 0.069 Uiso 1 1 calc R . . C143 C 0.0973(4) 0.3951(2) 0.3928(2) 0.0715(10) Uani 1 1 d . . . H143 H 0.0052 0.4327 0.3814 0.086 Uiso 1 1 calc R . . C144 C 0.2008(4) 0.3456(2) 0.3335(2) 0.0730(10) Uani 1 1 d . . . H144 H 0.1861 0.3466 0.2773 0.088 Uiso 1 1 calc R . . C145 C 0.3213(3) 0.29788(19) 0.37188(19) 0.0565(8) Uani 1 1 d . . . H145 H 0.4039 0.2603 0.3475 0.068 Uiso 1 1 calc R . . C221 C 0.4237(3) 0.29994(17) 0.05907(16) 0.0403(6) Uani 1 1 d . . . C222 C 0.4184(3) 0.38384(18) 0.07755(17) 0.0452(7) Uani 1 1 d . . . C223 C 0.3231(3) 0.45760(19) 0.03571(17) 0.0503(7) Uani 1 1 d . . . H223 H 0.3190 0.5145 0.0468 0.060 Uiso 1 1 calc R . . C224 C 0.2341(3) 0.44880(18) -0.02204(17) 0.0465(7) Uani 1 1 d . . . C225 C 0.2392(3) 0.36382(18) -0.03596(17) 0.0478(7) Uani 1 1 d . . . H225 H 0.1771 0.3571 -0.0733 0.057 Uiso 1 1 calc R . . C226 C 0.3336(3) 0.28791(17) 0.00364(16) 0.0421(6) Uani 1 1 d . . . C227 C 0.5161(3) 0.3947(2) 0.13951(19) 0.0632(9) Uani 1 1 d . . . H22A H 0.4976 0.4571 0.1443 0.095 Uiso 0.50 1 calc PR . . H22B H 0.6178 0.3728 0.1197 0.095 Uiso 0.50 1 calc PR . . H22C H 0.4952 0.3614 0.1940 0.095 Uiso 0.50 1 calc PR . . H22D H 0.5762 0.3371 0.1610 0.095 Uiso 0.50 1 calc PR . . H22E H 0.4560 0.4214 0.1857 0.095 Uiso 0.50 1 calc PR . . H22F H 0.5786 0.4328 0.1113 0.095 Uiso 0.50 1 calc PR . . C228 C 0.1361(3) 0.53028(19) -0.06989(19) 0.0619(8) Uani 1 1 d . . . H22G H 0.0827 0.5116 -0.1072 0.093 Uiso 0.50 1 calc PR . . H22H H 0.1957 0.5679 -0.1026 0.093 Uiso 0.50 1 calc PR . . H22I H 0.0674 0.5632 -0.0303 0.093 Uiso 0.50 1 calc PR . . H22J H 0.1479 0.5835 -0.0529 0.093 Uiso 0.50 1 calc PR . . H22K H 0.0348 0.5273 -0.0575 0.093 Uiso 0.50 1 calc PR . . H22L H 0.1631 0.5319 -0.1297 0.093 Uiso 0.50 1 calc PR . . C229 C 0.3419(3) 0.19690(18) -0.01601(19) 0.0594(8) Uani 1 1 d . . . H22M H 0.2712 0.2017 -0.0555 0.089 Uiso 0.50 1 calc PR . . H22N H 0.3203 0.1586 0.0353 0.089 Uiso 0.50 1 calc PR . . H22O H 0.4395 0.1720 -0.0405 0.089 Uiso 0.50 1 calc PR . . H22P H 0.4161 0.1531 0.0150 0.089 Uiso 0.50 1 calc PR . . H22Q H 0.3670 0.1963 -0.0758 0.089 Uiso 0.50 1 calc PR . . H22R H 0.2478 0.1828 0.0001 0.089 Uiso 0.50 1 calc PR . . C231 C 0.8854(3) 0.08475(17) 0.14075(15) 0.0405(6) Uani 1 1 d . . . C232 C 0.9304(3) -0.00189(17) 0.12126(16) 0.0460(7) Uani 1 1 d . . . C233 C 1.0785(3) -0.04468(18) 0.12213(17) 0.0520(7) Uani 1 1 d . . . H233 H 1.1105 -0.1026 0.1091 0.062 Uiso 1 1 calc R . . C234 C 1.1804(3) -0.00464(19) 0.14164(17) 0.0494(7) Uani 1 1 d . . . C235 C 1.1307(3) 0.08179(18) 0.16139(17) 0.0487(7) Uani 1 1 d . . . H235 H 1.1985 0.1092 0.1755 0.058 Uiso 1 1 calc R . . C236 C 0.9851(3) 0.12791(17) 0.16072(16) 0.0435(7) Uani 1 1 d . . . C237 C 0.8232(4) -0.0473(2) 0.0975(2) 0.0678(9) Uani 1 1 d . . . H23A H 0.7256 -0.0083 0.1002 0.102 Uiso 0.50 1 calc PR . . H23B H 0.8243 -0.1020 0.1363 0.102 Uiso 0.50 1 calc PR . . H23C H 0.8513 -0.0608 0.0408 0.102 Uiso 0.50 1 calc PR . . H23D H 0.8752 -0.1057 0.0847 0.102 Uiso 0.50 1 calc PR . . H23E H 0.7765 -0.0121 0.0486 0.102 Uiso 0.50 1 calc PR . . H23F H 0.7495 -0.0533 0.1441 0.102 Uiso 0.50 1 calc PR . . C238 C 1.3431(3) -0.0504(2) 0.1377(2) 0.0745(10) Uani 1 1 d . . . H23G H 1.3965 -0.0122 0.1533 0.112 Uiso 0.50 1 calc PR . . H23H H 1.3776 -0.0621 0.0810 0.112 Uiso 0.50 1 calc PR . . H23I H 1.3588 -0.1059 0.1763 0.112 Uiso 0.50 1 calc PR . . H23J H 1.3588 -0.1080 0.1204 0.112 Uiso 0.50 1 calc PR . . H23K H 1.3777 -0.0580 0.1927 0.112 Uiso 0.50 1 calc PR . . H23L H 1.3964 -0.0142 0.0974 0.112 Uiso 0.50 1 calc PR . . C239 C 0.9348(3) 0.22291(18) 0.1781(2) 0.0625(8) Uani 1 1 d . . . H23M H 0.8299 0.2438 0.1751 0.094 Uiso 0.50 1 calc PR . . H23N H 0.9839 0.2603 0.1366 0.094 Uiso 0.50 1 calc PR . . H23O H 0.9583 0.2253 0.2338 0.094 Uiso 0.50 1 calc PR . . H23P H 1.0182 0.2425 0.1885 0.094 Uiso 0.50 1 calc PR . . H23Q H 0.8641 0.2260 0.2271 0.094 Uiso 0.50 1 calc PR . . H23R H 0.8898 0.2610 0.1299 0.094 Uiso 0.50 1 calc PR . . C241 C 0.7542(3) 0.31304(16) -0.11516(16) 0.0376(6) Uani 1 1 d . . . C242 C 0.6847(3) 0.37581(17) -0.18473(16) 0.0425(6) Uani 1 1 d . . . H242 H 0.5852 0.3897 -0.1938 0.051 Uiso 1 1 calc R . . C243 C 0.7872(3) 0.40994(19) -0.23302(18) 0.0552(8) Uani 1 1 d . . . H243 H 0.7719 0.4526 -0.2816 0.066 Uiso 1 1 calc R . . C244 C 0.9265(3) 0.3701(2) -0.1979(2) 0.0768(11) Uani 1 1 d . . . H244 H 1.0162 0.3826 -0.2208 0.092 Uiso 1 1 calc R . . C245 C 0.9076(3) 0.3125(2) -0.1275(2) 0.0654(9) Uani 1 1 d . . . H245 H 0.9806 0.2785 -0.0930 0.078 Uiso 1 1 calc R . . N10 N 0.5120(2) 0.22664(13) 0.50350(13) 0.0421(5) Uani 1 1 d . . . N11 N 0.3847(2) 0.28777(13) 0.52015(14) 0.0418(5) Uani 1 1 d . . . N12 N 0.6058(2) 0.25332(14) 0.62944(13) 0.0431(5) Uani 1 1 d . . . N15 N 0.7133(2) 0.13394(14) 0.57341(14) 0.0463(6) Uani 1 1 d . . . N20 N 0.7589(2) 0.21945(13) 0.00795(13) 0.0412(5) Uani 1 1 d . . . N21 N 0.6784(2) 0.27356(13) -0.05384(13) 0.0402(5) Uani 1 1 d . . . N22 N 0.5272(2) 0.22367(14) 0.09971(13) 0.0426(5) Uani 1 1 d . . . N25 N 0.7324(2) 0.13132(14) 0.13998(13) 0.0433(5) 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 C11 0.0447(16) 0.0333(14) 0.0416(16) -0.0103(12) -0.0050(13) -0.0036(12) C13 0.0595(19) 0.0493(18) 0.0548(19) -0.0210(15) -0.0230(15) 0.0085(15) C14 0.0549(18) 0.0463(17) 0.0585(19) -0.0175(15) -0.0235(15) 0.0121(14) C21 0.0417(16) 0.0354(15) 0.0415(16) -0.0129(12) -0.0056(13) -0.0038(12) C23 0.0449(17) 0.0605(19) 0.0452(18) -0.0085(15) -0.0010(14) -0.0092(15) C24 0.0517(18) 0.0579(19) 0.0405(17) 0.0002(14) -0.0023(14) -0.0124(15) C121 0.0405(15) 0.0340(15) 0.0416(15) -0.0136(12) -0.0124(13) -0.0006(12) C122 0.0446(16) 0.0377(15) 0.0440(16) -0.0119(12) -0.0084(13) -0.0055(13) C123 0.0408(15) 0.0403(16) 0.0471(16) -0.0184(13) -0.0068(13) -0.0013(13) C124 0.0542(18) 0.0317(15) 0.0454(16) -0.0130(12) -0.0178(14) -0.0006(13) C125 0.0552(18) 0.0364(15) 0.0459(17) -0.0047(13) -0.0137(14) -0.0115(13) C126 0.0453(16) 0.0456(16) 0.0396(15) -0.0110(13) -0.0105(13) -0.0062(13) C127 0.072(2) 0.0470(18) 0.069(2) -0.0186(16) 0.0090(17) -0.0166(16) C128 0.076(2) 0.0355(16) 0.0577(19) -0.0175(14) -0.0188(16) 0.0025(14) C129 0.0570(19) 0.066(2) 0.0532(19) -0.0101(15) -0.0007(15) -0.0138(16) C131 0.0419(15) 0.0339(15) 0.0448(16) -0.0129(12) -0.0077(13) 0.0022(12) C132 0.0453(16) 0.0304(14) 0.0487(17) -0.0051(13) -0.0074(14) 0.0021(12) C133 0.0452(16) 0.0446(17) 0.0419(16) -0.0085(13) -0.0030(13) 0.0018(13) C134 0.0472(17) 0.0520(18) 0.0522(18) -0.0220(14) -0.0050(14) -0.0085(14) C135 0.064(2) 0.0458(17) 0.059(2) -0.0173(15) 0.0020(16) -0.0206(15) C136 0.0495(17) 0.0482(17) 0.0472(17) -0.0120(14) -0.0007(14) -0.0090(14) C137 0.080(2) 0.0399(17) 0.073(2) -0.0061(16) 0.0026(18) -0.0092(16) C138 0.080(2) 0.073(2) 0.076(2) -0.0420(19) -0.0003(19) -0.0237(19) C139 0.081(2) 0.076(2) 0.058(2) -0.0184(17) 0.0125(18) -0.0310(19) C141 0.0445(16) 0.0367(15) 0.0521(18) -0.0078(13) -0.0103(14) -0.0083(13) C142 0.0451(17) 0.0546(19) 0.072(2) -0.0163(16) -0.0123(16) -0.0043(15) C143 0.056(2) 0.063(2) 0.097(3) -0.005(2) -0.033(2) -0.0091(17) C144 0.082(3) 0.076(2) 0.065(2) -0.0052(19) -0.034(2) -0.017(2) C145 0.065(2) 0.0530(19) 0.0539(19) -0.0105(15) -0.0162(16) -0.0112(16) C221 0.0382(15) 0.0400(16) 0.0408(15) -0.0105(12) -0.0052(12) -0.0028(12) C222 0.0453(16) 0.0456(17) 0.0453(16) -0.0145(13) -0.0062(13) -0.0060(13) C223 0.0556(18) 0.0431(17) 0.0524(18) -0.0178(14) -0.0013(15) -0.0072(14) C224 0.0402(16) 0.0460(17) 0.0487(17) -0.0094(14) -0.0044(13) -0.0011(13) C225 0.0404(16) 0.0558(19) 0.0481(17) -0.0145(14) -0.0090(13) -0.0064(14) C226 0.0385(15) 0.0459(16) 0.0415(16) -0.0161(13) 0.0003(13) -0.0054(13) C227 0.070(2) 0.059(2) 0.069(2) -0.0194(17) -0.0212(17) -0.0165(17) C228 0.0560(19) 0.0553(19) 0.065(2) -0.0045(16) -0.0084(16) -0.0001(15) C229 0.070(2) 0.0539(19) 0.0591(19) -0.0178(15) -0.0161(16) -0.0125(16) C231 0.0445(16) 0.0386(15) 0.0337(14) -0.0049(12) -0.0050(12) -0.0021(13) C232 0.0581(18) 0.0404(16) 0.0379(16) -0.0065(12) -0.0061(13) -0.0080(14) C233 0.064(2) 0.0374(16) 0.0486(18) -0.0123(13) -0.0091(15) 0.0030(15) C234 0.0479(17) 0.0497(18) 0.0400(16) -0.0029(13) -0.0075(13) 0.0051(14) C235 0.0512(18) 0.0497(18) 0.0456(17) -0.0065(14) -0.0101(14) -0.0111(14) C236 0.0481(17) 0.0391(15) 0.0407(16) -0.0087(12) -0.0091(13) -0.0024(13) C237 0.086(2) 0.058(2) 0.068(2) -0.0169(17) -0.0170(18) -0.0235(18) C238 0.063(2) 0.069(2) 0.075(2) -0.0096(18) -0.0065(18) 0.0128(18) C239 0.071(2) 0.0443(18) 0.075(2) -0.0184(16) -0.0195(17) -0.0070(16) C241 0.0415(15) 0.0318(14) 0.0395(15) -0.0112(12) -0.0056(13) -0.0045(12) C242 0.0448(16) 0.0421(16) 0.0410(16) -0.0102(13) -0.0134(13) -0.0042(13) C243 0.063(2) 0.0524(18) 0.0478(18) 0.0013(14) -0.0134(16) -0.0127(16) C244 0.050(2) 0.087(3) 0.084(3) 0.025(2) -0.0116(18) -0.0239(18) C245 0.0463(18) 0.068(2) 0.072(2) 0.0146(18) -0.0140(16) -0.0099(16) N10 0.0438(13) 0.0353(12) 0.0463(14) -0.0121(10) -0.0095(11) -0.0015(10) N11 0.0410(13) 0.0338(12) 0.0499(14) -0.0108(10) -0.0054(11) -0.0045(10) N12 0.0433(13) 0.0385(13) 0.0446(13) -0.0134(10) -0.0110(11) 0.0027(10) N15 0.0482(14) 0.0381(13) 0.0492(14) -0.0169(11) -0.0111(11) 0.0053(11) N20 0.0442(13) 0.0360(12) 0.0390(13) -0.0041(10) -0.0074(11) -0.0016(10) N21 0.0452(13) 0.0353(12) 0.0376(13) -0.0119(10) -0.0074(11) 0.0003(10) N22 0.0431(13) 0.0441(13) 0.0379(13) -0.0090(10) -0.0060(10) -0.0032(11) N25 0.0431(13) 0.0406(13) 0.0422(13) -0.0038(10) -0.0049(11) -0.0045(11) _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 C11 N10 1.321(3) . ? C11 N12 1.360(3) . ? C11 N15 1.363(3) . ? C13 C14 1.327(3) . ? C13 N12 1.381(3) . ? C14 N15 1.380(3) . ? C21 N20 1.318(3) . ? C21 N25 1.361(3) . ? C21 N22 1.368(3) . ? C23 C24 1.324(4) . ? C23 N22 1.387(3) . ? C24 N25 1.385(3) . ? C121 C122 1.375(3) . ? C121 C126 1.380(3) . ? C121 N12 1.449(3) . ? C122 C123 1.389(3) . ? C122 C127 1.493(4) . ? C123 C124 1.379(4) . ? C124 C125 1.372(4) . ? C124 C128 1.511(3) . ? C125 C126 1.391(3) . ? C126 C129 1.499(3) . ? C131 C132 1.378(3) . ? C131 C136 1.378(4) . ? C131 N15 1.444(3) . ? C132 C133 1.392(3) . ? C132 C137 1.496(4) . ? C133 C134 1.379(4) . ? C134 C135 1.373(4) . ? C134 C138 1.510(4) . ? C135 C136 1.395(4) . ? C136 C139 1.504(4) . ? C141 N11 1.306(3) . ? C141 C142 1.441(4) . ? C141 C145 1.445(4) . ? C142 C143 1.329(4) . ? C143 C144 1.443(4) . ? C144 C145 1.340(4) . ? C221 C226 1.379(3) . ? C221 C222 1.385(3) . ? C221 N22 1.438(3) . ? C222 C223 1.385(4) . ? C222 C227 1.504(4) . ? C223 C224 1.379(4) . ? C224 C225 1.376(4) . ? C224 C228 1.509(4) . ? C225 C226 1.386(4) . ? C226 C229 1.494(4) . ? C231 C232 1.390(3) . ? C231 C236 1.393(4) . ? C231 N25 1.433(3) . ? C232 C233 1.379(4) . ? C232 C237 1.502(4) . ? C233 C234 1.373(4) . ? C234 C235 1.389(4) . ? C234 C238 1.507(4) . ? C235 C236 1.370(3) . ? C236 C239 1.502(3) . ? C241 N21 1.299(3) . ? C241 C245 1.431(4) . ? C241 C242 1.448(3) . ? C242 C243 1.320(4) . ? C243 C244 1.437(4) . ? C244 C245 1.336(4) . ? N10 N11 1.351(3) . ? N20 N21 1.354(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N10 C11 N12 133.1(2) . . ? N10 C11 N15 121.4(2) . . ? N12 C11 N15 105.5(2) . . ? C14 C13 N12 108.0(2) . . ? C13 C14 N15 107.4(2) . . ? N20 C21 N25 121.1(2) . . ? N20 C21 N22 132.6(2) . . ? N25 C21 N22 106.1(2) . . ? C24 C23 N22 108.3(2) . . ? C23 C24 N25 107.7(2) . . ? C122 C121 C126 123.4(2) . . ? C122 C121 N12 118.9(2) . . ? C126 C121 N12 117.5(2) . . ? C121 C122 C123 117.1(2) . . ? C121 C122 C127 121.4(2) . . ? C123 C122 C127 121.5(2) . . ? C124 C123 C122 121.9(2) . . ? C125 C124 C123 118.6(2) . . ? C125 C124 C128 120.8(3) . . ? C123 C124 C128 120.6(3) . . ? C124 C125 C126 122.0(3) . . ? C121 C126 C125 116.9(2) . . ? C121 C126 C129 121.8(2) . . ? C125 C126 C129 121.2(3) . . ? C132 C131 C136 123.0(2) . . ? C132 C131 N15 118.2(2) . . ? C136 C131 N15 118.7(2) . . ? C131 C132 C133 117.4(3) . . ? C131 C132 C137 121.8(2) . . ? C133 C132 C137 120.8(3) . . ? C134 C133 C132 121.7(3) . . ? C135 C134 C133 118.8(2) . . ? C135 C134 C138 119.8(3) . . ? C133 C134 C138 121.4(3) . . ? C134 C135 C136 121.7(3) . . ? C131 C136 C135 117.4(3) . . ? C131 C136 C139 122.4(2) . . ? C135 C136 C139 120.2(3) . . ? N11 C141 C142 122.6(3) . . ? N11 C141 C145 130.9(3) . . ? C142 C141 C145 106.4(2) . . ? C143 C142 C141 108.5(3) . . ? C142 C143 C144 108.4(3) . . ? C145 C144 C143 109.6(3) . . ? C144 C145 C141 107.1(3) . . ? C226 C221 C222 122.1(2) . . ? C226 C221 N22 119.8(2) . . ? C222 C221 N22 118.1(2) . . ? C223 C222 C221 118.0(2) . . ? C223 C222 C227 121.0(3) . . ? C221 C222 C227 121.0(2) . . ? C224 C223 C222 121.7(3) . . ? C225 C224 C223 118.2(3) . . ? C225 C224 C228 120.9(3) . . ? C223 C224 C228 120.9(3) . . ? C224 C225 C226 122.4(3) . . ? C221 C226 C225 117.5(2) . . ? C221 C226 C229 121.3(2) . . ? C225 C226 C229 121.1(2) . . ? C232 C231 C236 121.9(2) . . ? C232 C231 N25 119.2(2) . . ? C236 C231 N25 118.9(2) . . ? C233 C232 C231 117.8(3) . . ? C233 C232 C237 120.5(3) . . ? C231 C232 C237 121.7(3) . . ? C234 C233 C232 122.3(3) . . ? C233 C234 C235 118.1(3) . . ? C233 C234 C238 121.6(3) . . ? C235 C234 C238 120.2(3) . . ? C236 C235 C234 122.2(3) . . ? C235 C236 C231 117.8(2) . . ? C235 C236 C239 121.4(3) . . ? C231 C236 C239 120.8(2) . . ? N21 C241 C245 131.4(2) . . ? N21 C241 C242 122.0(2) . . ? C245 C241 C242 106.4(2) . . ? C243 C242 C241 108.1(2) . . ? C242 C243 C244 108.5(3) . . ? C245 C244 C243 109.7(3) . . ? C244 C245 C241 107.2(3) . . ? C11 N10 N11 111.6(2) . . ? C141 N11 N10 115.4(2) . . ? C11 N12 C13 109.4(2) . . ? C11 N12 C121 127.2(2) . . ? C13 N12 C121 122.5(2) . . ? C11 N15 C14 109.7(2) . . ? C11 N15 C131 124.0(2) . . ? C14 N15 C131 126.2(2) . . ? C21 N20 N21 111.9(2) . . ? C241 N21 N20 114.8(2) . . ? C21 N22 C23 108.6(2) . . ? C21 N22 C221 127.0(2) . . ? C23 N22 C221 123.4(2) . . ? C21 N25 C24 109.3(2) . . ? C21 N25 C231 124.3(2) . . ? C24 N25 C231 126.4(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.219 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.039 data_p212121 _database_code_depnum_ccdc_archive 'CCDC 236041' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 N2 S2' _chemical_formula_weight 294.38 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6383(4) _cell_length_b 10.1038(5) _cell_length_c 15.5131(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1353.98(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9222 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.51 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.382 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 12173 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3112 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0000P)^2^+0.7330P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(11) _refine_ls_number_reflns 3112 _refine_ls_number_parameters 242 _refine_ls_number_restraints 55 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.211 _refine_ls_restrained_S_all 1.204 _refine_ls_shift/su_max 0.391 _refine_ls_shift/su_mean 0.071 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 C1 C 0.0196(4) 0.8105(3) 0.8425(2) 0.0190(7) Uani 0.7527(12) 1 d PD A 1 C3 C 0.2819(6) 0.7852(4) 0.9182(3) 0.0266(9) Uani 0.7527(12) 1 d PD A 1 H3 H 0.3620 0.7875 0.9582 0.032 Uiso 0.7527(12) 1 calc PR A 1 C4 C 0.3005(5) 0.7285(5) 0.8422(3) 0.0237(9) Uani 0.7527(12) 1 d PD A 1 H4 H 0.3955 0.6934 0.8257 0.028 Uiso 0.7527(12) 1 calc PR A 1 C6 C -0.3272(6) 0.9573(8) 0.8709(5) 0.0208(11) Uani 0.7527(12) 1 d PD A 1 C7 C -0.4266(9) 0.9641(10) 0.7938(4) 0.0211(11) Uani 0.7527(12) 1 d PD A 1 C8 C -0.4097(5) 0.9116(6) 0.7117(3) 0.0214(10) Uani 0.7527(12) 1 d PD A 1 H8 H -0.3238 0.8607 0.6973 0.026 Uiso 0.7527(12) 1 calc PR A 1 C9 C -0.5261(8) 0.9376(7) 0.6513(4) 0.0285(12) Uani 0.7527(12) 1 d PD A 1 H9 H -0.5186 0.9002 0.5966 0.034 Uiso 0.7527(12) 1 calc PR A 1 C10 C -0.6526(13) 1.0175(17) 0.6701(7) 0.0347(16) Uani 0.7527(12) 1 d PD A 1 H10 H -0.7255 1.0367 0.6279 0.042 Uiso 0.7527(12) 1 calc PR A 1 C11 C -0.6691(19) 1.069(2) 0.7532(8) 0.0282(13) Uani 0.7527(12) 1 d PD A 1 H11 H -0.7564 1.1176 0.7678 0.034 Uiso 0.7527(12) 1 calc PR A 1 C12 C -0.5548(6) 1.0459(5) 0.8132(5) 0.0204(11) Uani 0.7527(12) 1 d PD A 1 C13 C -0.5479(11) 1.0789(12) 0.9060(4) 0.0203(11) Uani 0.7527(12) 1 d PD A 1 C14 C -0.6441(14) 1.1558(14) 0.9567(6) 0.0222(13) Uani 0.7527(12) 1 d PD A 1 H14 H -0.7333 1.1942 0.9343 0.027 Uiso 0.7527(12) 1 calc PR A 1 C15 C -0.6022(12) 1.1733(11) 1.0426(6) 0.0271(14) Uani 0.7527(12) 1 d PD A 1 H15 H -0.6660 1.2244 1.0777 0.032 Uiso 0.7527(12) 1 calc PR A 1 C16 C -0.4712(10) 1.1187(7) 1.0780(4) 0.0270(12) Uani 0.7527(12) 1 d PD A 1 H16 H -0.4498 1.1303 1.1363 0.032 Uiso 0.7527(12) 1 calc PR A 1 C17 C -0.3711(9) 1.0463(6) 1.0268(4) 0.0252(11) Uani 0.7527(12) 1 d PD A 1 H17 H -0.2798 1.0119 1.0493 0.030 Uiso 0.7527(12) 1 calc PR A 1 C18 C -0.4101(9) 1.0262(10) 0.9408(4) 0.0213(12) Uani 0.7527(12) 1 d PD A 1 N1 N -0.1219(4) 0.8385(3) 0.81935(19) 0.0256(6) Uani 0.7527(12) 1 d PD A 1 N2 N -0.1936(4) 0.9041(3) 0.8876(2) 0.0241(7) Uani 0.7527(12) 1 d PD A 1 S2 S 0.10279(11) 0.85539(10) 0.94078(6) 0.02485(19) Uani 0.7527(12) 1 d PD A 1 S5 S 0.14086(12) 0.72181(10) 0.77399(6) 0.0272(2) Uani 0.7527(12) 1 d PD A 1 C21 C 0.0249(11) 0.8363(10) 0.8926(6) 0.0190(7) Uani 0.2473(12) 1 d PD A 2 C23 C 0.2602(15) 0.7297(18) 0.8209(10) 0.0266(9) Uani 0.2473(12) 1 d PD A 2 H23 H 0.3266 0.6896 0.7816 0.032 Uiso 0.2473(12) 1 calc PR A 2 C24 C 0.3055(17) 0.7542(15) 0.8999(10) 0.0237(9) Uani 0.2473(12) 1 d PD A 2 H24 H 0.4063 0.7372 0.9178 0.028 Uiso 0.2473(12) 1 calc PR A 2 C26 C -0.338(2) 0.942(3) 0.8527(15) 0.0208(11) Uani 0.2473(12) 1 d PD A 2 C27 C -0.403(3) 1.021(3) 0.9240(13) 0.0211(11) Uani 0.2473(12) 1 d PD A 2 C28 C -0.368(3) 1.026(2) 1.0100(13) 0.0214(10) Uani 0.2473(12) 1 d PD A 2 H28 H -0.2817 0.9820 1.0313 0.026 Uiso 0.2473(12) 1 calc PR A 2 C29 C -0.462(4) 1.099(3) 1.0652(15) 0.0285(12) Uani 0.2473(12) 1 d PD A 2 H29 H -0.4317 1.1078 1.1224 0.034 Uiso 0.2473(12) 1 calc PR A 2 C210 C -0.601(4) 1.159(4) 1.040(2) 0.0347(16) Uani 0.2473(12) 1 d PD A 2 H210 H -0.6634 1.2062 1.0782 0.042 Uiso 0.2473(12) 1 calc PR A 2 C211 C -0.639(5) 1.144(5) 0.953(2) 0.0282(13) Uani 0.2473(12) 1 d PD A 2 H211 H -0.7333 1.1774 0.9331 0.034 Uiso 0.2473(12) 1 calc PR A 2 C212 C -0.542(3) 1.081(3) 0.8958(13) 0.0204(11) Uani 0.2473(12) 1 d PD A 2 C213 C -0.574(2) 1.028(2) 0.8100(14) 0.0203(11) Uani 0.2473(12) 1 d PD A 2 C214 C -0.682(6) 1.071(7) 0.751(2) 0.0222(13) Uani 0.2473(12) 1 d PD A 2 H214 H -0.7601 1.1302 0.7667 0.027 Uiso 0.2473(12) 1 calc PR A 2 C215 C -0.671(4) 1.024(5) 0.6670(18) 0.0271(14) Uani 0.2473(12) 1 d PD A 2 H215 H -0.7512 1.0446 0.6292 0.032 Uiso 0.2473(12) 1 calc PR A 2 C216 C -0.551(2) 0.950(2) 0.6358(13) 0.0270(12) Uani 0.2473(12) 1 d PD A 2 H216 H -0.5449 0.9252 0.5783 0.032 Uiso 0.2473(12) 1 calc PR A 2 C217 C -0.441(2) 0.916(2) 0.6948(12) 0.0252(11) Uani 0.2473(12) 1 d PD A 2 H217 H -0.3650 0.8556 0.6783 0.030 Uiso 0.2473(12) 1 calc PR A 2 C218 C -0.437(3) 0.965(4) 0.7776(13) 0.0213(12) Uani 0.2473(12) 1 d PD A 2 N21 N -0.1105(11) 0.8900(10) 0.9123(6) 0.0256(6) Uani 0.2473(12) 1 d PD A 2 N22 N -0.2020(11) 0.8880(11) 0.8400(7) 0.0241(7) Uani 0.2473(12) 1 d PD A 2 S22 S 0.0750(4) 0.7733(3) 0.79157(19) 0.02485(19) Uani 0.2473(12) 1 d PD A 2 S25 S 0.1666(4) 0.8209(3) 0.9707(2) 0.0272(2) Uani 0.2473(12) 1 d PD A 2 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 C1 0.0220(16) 0.0198(16) 0.0152(16) -0.0027(14) 0.0007(15) 0.0045(13) C3 0.020(2) 0.028(2) 0.032(2) 0.0075(19) -0.0014(16) 0.0001(17) C4 0.0123(18) 0.0222(17) 0.037(3) 0.001(2) 0.0007(16) 0.0033(16) C6 0.0185(17) 0.016(3) 0.028(4) -0.001(2) -0.0011(16) -0.0039(17) C7 0.024(2) 0.0181(17) 0.021(3) 0.007(2) 0.001(2) -0.0035(18) C8 0.018(2) 0.0203(17) 0.026(2) 0.0014(18) -0.0028(17) -0.0015(18) C9 0.041(3) 0.024(2) 0.020(3) 0.0034(19) -0.002(2) -0.006(2) C10 0.036(4) 0.032(3) 0.036(3) 0.002(2) -0.011(3) -0.010(3) C11 0.026(4) 0.022(3) 0.036(3) 0.004(2) -0.005(2) -0.003(3) C12 0.015(2) 0.014(2) 0.032(2) 0.0004(17) 0.0025(17) -0.0116(15) C13 0.023(2) 0.0217(18) 0.016(2) 0.004(2) 0.000(2) 0.0014(17) C14 0.021(2) 0.019(4) 0.027(2) 0.0008(19) 0.0042(18) -0.001(2) C15 0.026(2) 0.023(3) 0.032(2) -0.0032(19) 0.010(2) -0.005(2) C16 0.033(2) 0.027(3) 0.022(3) -0.0043(17) 0.000(2) -0.009(2) C17 0.0230(19) 0.025(3) 0.027(3) -0.0048(17) -0.006(2) -0.002(2) C18 0.018(2) 0.0215(19) 0.024(3) 0.003(3) 0.000(2) -0.0027(15) N1 0.0214(15) 0.0302(16) 0.0252(15) -0.0038(13) 0.0005(13) 0.0063(13) N2 0.0202(14) 0.0276(15) 0.0245(18) -0.0007(16) 0.0021(15) 0.0027(12) S2 0.0196(4) 0.0295(4) 0.0255(4) -0.0020(4) -0.0017(4) 0.0020(4) S5 0.0242(4) 0.0297(4) 0.0277(5) -0.0012(4) 0.0026(4) 0.0069(4) C21 0.0220(16) 0.0198(16) 0.0152(16) -0.0027(14) 0.0007(15) 0.0045(13) C23 0.020(2) 0.028(2) 0.032(2) 0.0075(19) -0.0014(16) 0.0001(17) C24 0.0123(18) 0.0222(17) 0.037(3) 0.001(2) 0.0007(16) 0.0033(16) C26 0.0185(17) 0.016(3) 0.028(4) -0.001(2) -0.0011(16) -0.0039(17) C27 0.024(2) 0.0181(17) 0.021(3) 0.007(2) 0.001(2) -0.0035(18) C28 0.018(2) 0.0203(17) 0.026(2) 0.0014(18) -0.0028(17) -0.0015(18) C29 0.041(3) 0.024(2) 0.020(3) 0.0034(19) -0.002(2) -0.006(2) C210 0.036(4) 0.032(3) 0.036(3) 0.002(2) -0.011(3) -0.010(3) C211 0.026(4) 0.022(3) 0.036(3) 0.004(2) -0.005(2) -0.003(3) C212 0.015(2) 0.014(2) 0.032(2) 0.0004(17) 0.0025(17) -0.0116(15) C213 0.023(2) 0.0217(18) 0.016(2) 0.004(2) 0.000(2) 0.0014(17) C214 0.021(2) 0.019(4) 0.027(2) 0.0008(19) 0.0042(18) -0.001(2) C215 0.026(2) 0.023(3) 0.032(2) -0.0032(19) 0.010(2) -0.005(2) C216 0.033(2) 0.027(3) 0.022(3) -0.0043(17) 0.000(2) -0.009(2) C217 0.0230(19) 0.025(3) 0.027(3) -0.0048(17) -0.006(2) -0.002(2) C218 0.018(2) 0.0215(19) 0.024(3) 0.003(3) 0.000(2) -0.0027(15) N21 0.0214(15) 0.0302(16) 0.0252(15) -0.0038(13) 0.0005(13) 0.0063(13) N22 0.0202(14) 0.0276(15) 0.0245(18) -0.0007(16) 0.0021(15) 0.0027(12) S22 0.0196(4) 0.0295(4) 0.0255(4) -0.0020(4) -0.0017(4) 0.0020(4) S25 0.0242(4) 0.0297(4) 0.0277(5) -0.0012(4) 0.0026(4) 0.0069(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 C1 N1 1.306(4) . ? C1 S5 1.741(3) . ? C1 S2 1.745(3) . ? C3 C4 1.321(6) . ? C3 S2 1.738(5) . ? C4 S5 1.739(4) . ? C6 N2 1.299(5) . ? C6 C18 1.474(6) . ? C6 C7 1.475(6) . ? C7 C8 1.387(7) . ? C7 C12 1.415(7) . ? C8 C9 1.400(6) . ? C9 C10 1.390(10) . ? C10 C11 1.395(10) . ? C11 C12 1.376(9) . ? C12 C13 1.478(6) . ? C13 C14 1.383(8) . ? C13 C18 1.411(8) . ? C14 C15 1.393(9) . ? C15 C16 1.374(9) . ? C16 C17 1.383(7) . ? C17 C18 1.391(7) . ? N1 N2 1.394(4) . ? C21 N21 1.324(11) . ? C21 S25 1.730(9) . ? C21 S22 1.746(9) . ? C23 C24 1.310(14) . ? C23 S22 1.721(12) . ? C24 S25 1.760(12) . ? C26 N22 1.312(14) . ? C26 C218 1.461(17) . ? C26 C27 1.479(17) . ? C27 C28 1.370(18) . ? C27 C212 1.413(19) . ? C28 C29 1.392(17) . ? C29 C210 1.40(2) . ? C210 C211 1.40(2) . ? C211 C212 1.38(2) . ? C212 C213 1.461(14) . ? C213 C214 1.38(2) . ? C213 C218 1.438(19) . ? C214 C215 1.39(2) . ? C215 C216 1.37(2) . ? C216 C217 1.365(15) . ? C217 C218 1.380(18) . ? N21 N22 1.372(11) . ? 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 N1 C1 S5 120.5(3) . . ? N1 C1 S2 124.7(3) . . ? S5 C1 S2 114.8(2) . . ? C4 C3 S2 117.7(4) . . ? C3 C4 S5 117.6(4) . . ? N2 C6 C18 118.7(5) . . ? N2 C6 C7 134.3(5) . . ? C18 C6 C7 107.0(4) . . ? C8 C7 C12 120.1(5) . . ? C8 C7 C6 131.8(5) . . ? C12 C7 C6 108.0(5) . . ? C7 C8 C9 117.9(5) . . ? C10 C9 C8 122.2(6) . . ? C11 C10 C9 119.4(7) . . ? C12 C11 C10 119.3(9) . . ? C11 C12 C7 121.0(7) . . ? C11 C12 C13 130.5(8) . . ? C7 C12 C13 107.9(6) . . ? C14 C13 C18 120.1(7) . . ? C14 C13 C12 131.0(7) . . ? C18 C13 C12 108.8(6) . . ? C13 C14 C15 117.4(8) . . ? C16 C15 C14 123.1(6) . . ? C15 C16 C17 119.8(6) . . ? C16 C17 C18 118.5(6) . . ? C17 C18 C13 121.1(5) . . ? C17 C18 C6 131.0(5) . . ? C13 C18 C6 107.9(5) . . ? C1 N1 N2 108.1(3) . . ? C6 N2 N1 116.1(4) . . ? C3 S2 C1 94.8(2) . . ? C4 S5 C1 94.91(19) . . ? N21 C21 S25 120.0(7) . . ? N21 C21 S22 125.2(8) . . ? S25 C21 S22 114.8(5) . . ? C24 C23 S22 118.5(13) . . ? C23 C24 S25 116.9(13) . . ? N22 C26 C218 118.1(17) . . ? N22 C26 C27 132.6(15) . . ? C218 C26 C27 106.7(11) . . ? C28 C27 C212 118.3(16) . . ? C28 C27 C26 131.6(18) . . ? C212 C27 C26 108.9(15) . . ? C27 C28 C29 119.2(19) . . ? C28 C29 C210 124(2) . . ? C211 C210 C29 115(2) . . ? C212 C211 C210 122(2) . . ? C211 C212 C27 121.1(19) . . ? C211 C212 C213 130(2) . . ? C27 C212 C213 106.7(18) . . ? C214 C213 C218 117.8(19) . . ? C214 C213 C212 128(2) . . ? C218 C213 C212 108.9(17) . . ? C213 C214 C215 118(2) . . ? C216 C215 C214 125(2) . . ? C215 C216 C217 116(2) . . ? C216 C217 C218 123.3(18) . . ? C217 C218 C213 117.6(16) . . ? C217 C218 C26 134.3(17) . . ? C213 C218 C26 105.9(14) . . ? C21 N21 N22 108.3(8) . . ? C26 N22 N21 113.0(11) . . ? C23 S22 C21 95.0(6) . . ? C21 S25 C24 94.6(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.275 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.053