# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Peter Holliman' _publ_contact_author_email p.j.holliman@bangor.ac.uk _publ_contact_author_address ; School of Chemistry, Bangor University, Gwynedd LL57 2UW, Unioted Kingdom ; _publ_contact_author_phone '(+44) 01248 383635' loop_ _publ_author_name _publ_author_address 'Peter J. Holliman' ;School of Chemistry, Bangor University, Gwynedd LL57 2UW, United Kingdom ; 'Moneer Mohsen' ;School of Chemistry, Bangor University, Gwynedd LL57 2UW, United Kingdom ; 'Arthur Connell' ;School of Chemistry, Bangor University, Gwynedd LL57 2UW, United Kingdom ; 'Matthew L. Davies' ;School of Chemistry, Bangor University, Gwynedd LL57 2UW, United Kingdom ; 'Mateusz B. Pitak' ;School of Chemistry, University of Southampton, Highfield Campus, Southampton SO17 1BJ, United Kingdom ; ; G.J.Tizzard ; ;School of Chemistry, University of Southampton, Highfield Campus, Southampton SO17 1BJ, United Kingdom ; 'Simon J. Coles' ;School of Chemistry, University of Southampton, Highfield Campus, Southampton SO17 1BJ, United Kingdom ; 'Ross W. Harrington' ;School of Chemistry, Newcastle University, Newcastle upon Tyne NE1 7RU, United Kingdom ; 'William Clegg' ;School of Chemistry, Newcastle University, Newcastle upon Tyne NE1 7RU, United Kingdom ; 'Carlos Serpa' 'Chemistry Department, University of Coimbra, P3004-535 Coimbra, Portugal' 'Octavio Fontes ' 'Chemistry Department, University of Coimbra, P3004-535 Coimbra, Portugal' _publ_section_title ; Ultra-fast Co-Sensitization and Tri-Sensitization of Dye-Sensitized Solar Cells with N719, SQ1 and Triarylamine Dyes ; #TrackingRef '- Holliman_dyes_combined.cif' _publ_contact_author 'Mateusz B. Pitak' #===END ############################################################## data_2009src1319_compound_3 _database_code_depnum_ccdc_archive 'CCDC 838485' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H21 N O' _chemical_formula_sum 'C27 H21 N O' _chemical_formula_weight 375.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1895(10) _cell_length_b 11.4764(16) _cell_length_c 17.763(3) _cell_angle_alpha 102.487(5) _cell_angle_beta 96.931(8) _cell_angle_gamma 101.360(8) _cell_volume 1959.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 71743 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9692 _exptl_absorpt_correction_T_max 0.9962 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.5177 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30858 _diffrn_reflns_av_R_equivalents 0.1570 _diffrn_reflns_av_sigmaI/netI 0.1511 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6734 _reflns_number_gt 3732 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (L. J. Farrugia 1997)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0852P)^2^+1.1548P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6734 _refine_ls_number_parameters 523 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1911 _refine_ls_R_factor_gt 0.1076 _refine_ls_wR_factor_ref 0.2430 _refine_ls_wR_factor_gt 0.2051 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 O1 O 0.2531(4) 0.6488(4) 0.6117(3) 0.0670(11) Uani 1 1 d . . . N1 N -0.0966(4) 1.2972(3) 0.1396(3) 0.0440(10) Uani 1 1 d . . . C1 C -0.1400(4) 1.4079(4) 0.1580(3) 0.0373(11) Uani 1 1 d . . . C2 C -0.2062(4) 1.4347(4) 0.2210(3) 0.0440(12) Uani 1 1 d . . . H2 H -0.2204 1.3792 0.2534 0.053 Uiso 1 1 calc R . . C3 C -0.2521(5) 1.5426(4) 0.2371(3) 0.0518(14) Uani 1 1 d . . . H3 H -0.2945 1.5619 0.2815 0.062 Uiso 1 1 calc R . . C4 C -0.2361(6) 1.6214(5) 0.1884(4) 0.0612(16) Uani 1 1 d . . . H4 H -0.2711 1.6931 0.1980 0.073 Uiso 1 1 calc R . . C5 C -0.1697(5) 1.5963(4) 0.1264(4) 0.0553(15) Uani 1 1 d . . . H5 H -0.1558 1.6523 0.0942 0.066 Uiso 1 1 calc R . . C6 C -0.1222(5) 1.4892(4) 0.1100(3) 0.0501(13) Uani 1 1 d . . . H6 H -0.0779 1.4715 0.0662 0.060 Uiso 1 1 calc R . . C7 C -0.0958(5) 1.2381(4) 0.0604(3) 0.0416(12) Uani 1 1 d . . . C8 C -0.2083(5) 1.2187(4) 0.0021(3) 0.0467(13) Uani 1 1 d . . . H8 H -0.2868 1.2462 0.0149 0.056 Uiso 1 1 calc R . . C9 C -0.2064(5) 1.1595(4) -0.0745(3) 0.0465(12) Uani 1 1 d . . . H9 H -0.2825 1.1477 -0.1142 0.056 Uiso 1 1 calc R . . C10 C -0.0937(5) 1.1181(4) -0.0927(3) 0.0442(12) Uani 1 1 d . . . H10 H -0.0926 1.0766 -0.1449 0.053 Uiso 1 1 calc R . . C11 C 0.0163(5) 1.1363(4) -0.0363(3) 0.0439(12) Uani 1 1 d . . . H11 H 0.0938 1.1073 -0.0494 0.053 Uiso 1 1 calc R . . C12 C 0.0164(4) 1.1964(4) 0.0397(3) 0.0419(12) Uani 1 1 d . . . H12 H 0.0943 1.2094 0.0784 0.050 Uiso 1 1 calc R . . C13 C -0.0666(4) 1.2334(4) 0.1968(3) 0.0401(12) Uani 1 1 d . . . C14 C -0.1115(4) 1.1052(4) 0.1776(3) 0.0401(12) Uani 1 1 d . . . H14 H -0.1631 1.0635 0.1274 0.048 Uiso 1 1 calc R . . C15 C -0.0809(4) 1.0394(4) 0.2313(3) 0.0438(12) Uani 1 1 d . . . H15 H -0.1111 0.9526 0.2170 0.053 Uiso 1 1 calc R . . C16 C -0.0077(4) 1.0961(4) 0.3052(3) 0.0413(12) Uani 1 1 d . . . C17 C 0.0332(4) 1.2244(4) 0.3249(3) 0.0413(12) Uani 1 1 d . . . H17 H 0.0811 1.2663 0.3759 0.050 Uiso 1 1 calc R . . C18 C 0.0047(4) 1.2910(4) 0.2710(3) 0.0451(13) Uani 1 1 d . . . H18 H 0.0348 1.3778 0.2853 0.054 Uiso 1 1 calc R . . C19 C 0.0343(4) 1.0275(4) 0.3614(3) 0.0415(12) Uani 1 1 d . . . H19 H 0.0696 1.0732 0.4137 0.050 Uiso 1 1 calc R . . C20 C 0.0275(4) 0.9075(4) 0.3457(3) 0.0431(12) Uani 1 1 d . . . H20 H -0.0098 0.8629 0.2933 0.052 Uiso 1 1 calc R . . C21 C 0.0700(4) 0.8358(4) 0.3985(3) 0.0399(12) Uani 1 1 d . . . C22 C 0.0496(5) 0.7098(4) 0.3713(3) 0.0474(13) Uani 1 1 d . . . H22 H 0.0106 0.6719 0.3181 0.057 Uiso 1 1 calc R . . C23 C 0.0850(5) 0.6387(4) 0.4202(3) 0.0484(13) Uani 1 1 d . . . H23 H 0.0683 0.5524 0.4004 0.058 Uiso 1 1 calc R . . C24 C 0.1444(4) 0.6905(4) 0.4976(3) 0.0415(12) Uani 1 1 d . . . C25 C 0.1681(4) 0.8165(4) 0.5253(3) 0.0471(13) Uani 1 1 d . . . H25 H 0.2104 0.8540 0.5780 0.057 Uiso 1 1 calc R . . C26 C 0.1306(5) 0.8885(4) 0.4769(3) 0.0444(12) Uani 1 1 d . . . H26 H 0.1462 0.9746 0.4971 0.053 Uiso 1 1 calc R . . C27 C 0.1836(5) 0.6122(5) 0.5476(4) 0.0537(14) Uani 1 1 d . . . H27 H 0.1518 0.5260 0.5280 0.064 Uiso 1 1 calc R . . O101 O 0.2978(4) 1.4413(3) 0.4309(2) 0.0664(11) Uani 1 1 d . . . N101 N 0.6030(4) 0.7053(3) 0.8635(2) 0.0440(10) Uani 1 1 d . . . C101 C 0.6446(4) 0.5958(4) 0.8340(3) 0.0412(12) Uani 1 1 d . . . C102 C 0.6045(5) 0.5349(5) 0.7564(3) 0.0540(14) Uani 1 1 d . . . H102 H 0.5475 0.5659 0.7232 0.065 Uiso 1 1 calc R . . C103 C 0.6458(6) 0.4292(5) 0.7259(4) 0.0648(16) Uani 1 1 d . . . H103 H 0.6194 0.3897 0.6718 0.078 Uiso 1 1 calc R . . C104 C 0.7248(6) 0.3812(5) 0.7737(5) 0.0669(18) Uani 1 1 d . . . H104 H 0.7528 0.3082 0.7533 0.080 Uiso 1 1 calc R . . C105 C 0.7627(5) 0.4404(5) 0.8514(4) 0.0570(15) Uani 1 1 d . . . H105 H 0.8162 0.4068 0.8848 0.068 Uiso 1 1 calc R . . C106 C 0.7252(4) 0.5477(4) 0.8824(3) 0.0475(13) Uani 1 1 d . . . H106 H 0.7541 0.5882 0.9363 0.057 Uiso 1 1 calc R . . C107 C 0.5824(4) 0.7418(4) 0.9418(3) 0.0407(12) Uani 1 1 d . . . C108 C 0.5298(5) 0.6562(4) 0.9814(3) 0.0448(13) Uani 1 1 d . . . H108 H 0.5041 0.5717 0.9552 0.054 Uiso 1 1 calc R . . C109 C 0.5145(5) 0.6930(5) 1.0582(3) 0.0479(13) Uani 1 1 d . . . H109 H 0.4826 0.6333 1.0854 0.058 Uiso 1 1 calc R . . C110 C 0.5453(4) 0.8162(5) 1.0961(3) 0.0463(13) Uani 1 1 d . . . H110 H 0.5355 0.8417 1.1493 0.056 Uiso 1 1 calc R . . C111 C 0.5904(4) 0.9011(4) 1.0553(3) 0.0445(13) Uani 1 1 d . . . H111 H 0.6075 0.9860 1.0801 0.053 Uiso 1 1 calc R . . C112 C 0.6112(4) 0.8657(4) 0.9798(3) 0.0405(12) Uani 1 1 d . . . H112 H 0.6454 0.9257 0.9534 0.049 Uiso 1 1 calc R . . C113 C 0.5826(4) 0.7841(4) 0.8134(3) 0.0393(11) Uani 1 1 d . . . C114 C 0.4631(4) 0.8264(4) 0.8065(3) 0.0422(12) Uani 1 1 d . . . H114 H 0.3949 0.8031 0.8359 0.051 Uiso 1 1 calc R . . C115 C 0.4438(4) 0.9016(4) 0.7575(3) 0.0402(12) Uani 1 1 d . . . H115 H 0.3608 0.9274 0.7525 0.048 Uiso 1 1 calc R . . C116 C 0.5425(4) 0.9406(4) 0.7154(3) 0.0415(12) Uani 1 1 d . . . C117 C 0.6614(4) 0.8976(4) 0.7230(3) 0.0432(12) Uani 1 1 d . . . H117 H 0.7298 0.9216 0.6938 0.052 Uiso 1 1 calc R . . C118 C 0.6827(5) 0.8218(4) 0.7712(3) 0.0432(12) Uani 1 1 d . . . H118 H 0.7653 0.7952 0.7757 0.052 Uiso 1 1 calc R . . C119 C 0.5283(5) 1.0207(4) 0.6633(3) 0.0415(12) Uani 1 1 d . . . H119 H 0.6011 1.0373 0.6356 0.050 Uiso 1 1 calc R . . C120 C 0.4254(5) 1.0742(4) 0.6495(3) 0.0426(12) Uani 1 1 d . . . H120 H 0.3534 1.0614 0.6784 0.051 Uiso 1 1 calc R . . C121 C 0.4140(4) 1.1505(4) 0.5939(3) 0.0423(12) Uani 1 1 d . . . C122 C 0.3109(5) 1.2148(4) 0.5937(3) 0.0471(13) Uani 1 1 d . . . H122 H 0.2490 1.2079 0.6292 0.057 Uiso 1 1 calc R . . C123 C 0.2980(5) 1.2889(4) 0.5420(3) 0.0487(13) Uani 1 1 d . . . H123 H 0.2268 1.3312 0.5420 0.058 Uiso 1 1 calc R . . C124 C 0.3888(5) 1.3010(4) 0.4909(3) 0.0438(12) Uani 1 1 d . . . C125 C 0.4895(5) 1.2363(4) 0.4903(3) 0.0437(12) Uani 1 1 d . . . H125 H 0.5508 1.2430 0.4544 0.052 Uiso 1 1 calc R . . C126 C 0.5028(5) 1.1626(4) 0.5408(3) 0.0454(13) Uani 1 1 d . . . H126 H 0.5733 1.1193 0.5395 0.054 Uiso 1 1 calc R . . C127 C 0.3811(5) 1.3814(4) 0.4365(3) 0.0517(14) Uani 1 1 d . . . H127 H 0.4474 1.3861 0.4034 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.082(3) 0.077(3) 0.052(3) 0.031(2) 0.012(2) 0.025(2) N1 0.058(2) 0.039(2) 0.044(3) 0.016(2) 0.013(2) 0.0215(18) C1 0.042(2) 0.034(3) 0.036(3) 0.009(2) 0.004(2) 0.0105(19) C2 0.042(3) 0.035(3) 0.052(4) 0.008(2) 0.001(2) 0.008(2) C3 0.053(3) 0.052(3) 0.047(4) 0.007(3) -0.006(2) 0.018(2) C4 0.072(4) 0.050(3) 0.059(4) 0.005(3) -0.008(3) 0.028(3) C5 0.065(3) 0.039(3) 0.060(4) 0.022(3) -0.011(3) 0.009(2) C6 0.056(3) 0.045(3) 0.050(4) 0.017(3) 0.000(3) 0.013(2) C7 0.051(3) 0.036(3) 0.043(4) 0.017(3) 0.010(2) 0.014(2) C8 0.055(3) 0.045(3) 0.049(4) 0.023(3) 0.013(3) 0.016(2) C9 0.055(3) 0.051(3) 0.037(4) 0.014(3) 0.006(2) 0.017(2) C10 0.059(3) 0.041(3) 0.038(3) 0.014(2) 0.017(3) 0.017(2) C11 0.047(3) 0.044(3) 0.046(4) 0.016(3) 0.015(3) 0.014(2) C12 0.043(3) 0.041(3) 0.046(4) 0.019(3) 0.007(2) 0.014(2) C13 0.044(3) 0.039(3) 0.043(3) 0.015(3) 0.011(2) 0.019(2) C14 0.042(2) 0.040(3) 0.044(3) 0.016(3) 0.008(2) 0.014(2) C15 0.045(3) 0.038(3) 0.051(4) 0.013(3) 0.011(2) 0.011(2) C16 0.044(3) 0.046(3) 0.040(3) 0.018(3) 0.011(2) 0.017(2) C17 0.044(3) 0.041(3) 0.040(3) 0.008(2) 0.009(2) 0.014(2) C18 0.049(3) 0.041(3) 0.049(4) 0.013(3) 0.009(3) 0.015(2) C19 0.037(2) 0.043(3) 0.046(3) 0.013(3) 0.010(2) 0.010(2) C20 0.044(3) 0.046(3) 0.045(3) 0.017(3) 0.013(2) 0.016(2) C21 0.039(2) 0.040(3) 0.047(4) 0.015(3) 0.012(2) 0.016(2) C22 0.059(3) 0.040(3) 0.044(3) 0.012(3) 0.005(2) 0.014(2) C23 0.048(3) 0.040(3) 0.059(4) 0.015(3) 0.006(3) 0.013(2) C24 0.050(3) 0.040(3) 0.040(3) 0.015(3) 0.010(2) 0.016(2) C25 0.047(3) 0.051(3) 0.046(4) 0.016(3) 0.008(2) 0.012(2) C26 0.057(3) 0.039(3) 0.042(4) 0.016(3) 0.015(3) 0.013(2) C27 0.056(3) 0.053(3) 0.066(5) 0.027(3) 0.026(3) 0.024(3) O101 0.083(3) 0.056(2) 0.072(3) 0.028(2) 0.013(2) 0.029(2) N101 0.062(2) 0.036(2) 0.039(3) 0.011(2) 0.010(2) 0.0177(18) C101 0.045(3) 0.034(3) 0.045(4) 0.009(3) 0.016(2) 0.006(2) C102 0.068(3) 0.044(3) 0.051(4) 0.015(3) 0.015(3) 0.010(2) C103 0.089(4) 0.041(3) 0.062(4) 0.003(3) 0.028(3) 0.010(3) C104 0.083(4) 0.035(3) 0.091(6) 0.013(4) 0.045(4) 0.018(3) C105 0.056(3) 0.048(3) 0.080(5) 0.027(3) 0.027(3) 0.023(2) C106 0.047(3) 0.038(3) 0.062(4) 0.018(3) 0.016(3) 0.012(2) C107 0.044(3) 0.040(3) 0.045(3) 0.016(3) 0.011(2) 0.017(2) C108 0.059(3) 0.035(3) 0.050(4) 0.017(3) 0.017(3) 0.019(2) C109 0.061(3) 0.048(3) 0.051(4) 0.027(3) 0.024(3) 0.027(2) C110 0.049(3) 0.058(3) 0.042(3) 0.016(3) 0.012(2) 0.028(2) C111 0.044(3) 0.042(3) 0.049(4) 0.015(3) 0.002(2) 0.016(2) C112 0.041(2) 0.039(3) 0.047(4) 0.016(3) 0.010(2) 0.014(2) C113 0.051(3) 0.033(3) 0.034(3) 0.006(2) 0.008(2) 0.009(2) C114 0.047(3) 0.043(3) 0.038(3) 0.007(2) 0.013(2) 0.013(2) C115 0.041(3) 0.040(3) 0.040(3) 0.009(2) 0.005(2) 0.015(2) C116 0.047(3) 0.036(3) 0.042(3) 0.009(2) 0.011(2) 0.009(2) C117 0.039(3) 0.048(3) 0.049(4) 0.019(3) 0.012(2) 0.013(2) C118 0.049(3) 0.046(3) 0.041(3) 0.013(3) 0.010(2) 0.019(2) C119 0.047(3) 0.040(3) 0.039(3) 0.009(2) 0.012(2) 0.011(2) C120 0.052(3) 0.041(3) 0.039(3) 0.012(2) 0.013(2) 0.015(2) C121 0.045(3) 0.035(3) 0.046(3) 0.011(2) 0.004(2) 0.008(2) C122 0.053(3) 0.043(3) 0.051(4) 0.015(3) 0.017(2) 0.015(2) C123 0.057(3) 0.046(3) 0.048(4) 0.013(3) 0.008(3) 0.022(2) C124 0.055(3) 0.035(3) 0.038(3) 0.006(2) 0.001(2) 0.010(2) C125 0.056(3) 0.042(3) 0.033(3) 0.009(2) 0.011(2) 0.009(2) C126 0.048(3) 0.044(3) 0.044(4) 0.011(3) 0.004(2) 0.012(2) C127 0.058(3) 0.046(3) 0.051(4) 0.014(3) 0.004(3) 0.014(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 C27 1.205(7) . ? N1 C13 1.413(6) . ? N1 C1 1.413(6) . ? N1 C7 1.425(6) . ? C1 C2 1.383(7) . ? C1 C6 1.394(6) . ? C2 C3 1.393(6) . ? C2 H2 0.9500 . ? C3 C4 1.381(7) . ? C3 H3 0.9500 . ? C4 C5 1.370(8) . ? C4 H4 0.9500 . ? C5 C6 1.394(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.383(6) . ? C7 C8 1.397(7) . ? C8 C9 1.388(7) . ? C8 H8 0.9500 . ? C9 C10 1.373(6) . ? C9 H9 0.9500 . ? C10 C11 1.361(7) . ? C10 H10 0.9500 . ? C11 C12 1.376(7) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.380(7) . ? C13 C14 1.403(6) . ? C14 C15 1.383(6) . ? C14 H14 0.9500 . ? C15 C16 1.380(7) . ? C15 H15 0.9500 . ? C16 C17 1.402(6) . ? C16 C19 1.472(6) . ? C17 C18 1.386(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.331(6) . ? C19 H19 0.9500 . ? C20 C21 1.457(6) . ? C20 H20 0.9500 . ? C21 C22 1.387(6) . ? C21 C26 1.402(7) . ? C22 C23 1.377(6) . ? C22 H22 0.9500 . ? C23 C24 1.384(7) . ? C23 H23 0.9500 . ? C24 C25 1.385(6) . ? C24 C27 1.469(7) . ? C25 C26 1.385(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? O101 C127 1.200(5) . ? N101 C107 1.417(6) . ? N101 C101 1.419(6) . ? N101 C113 1.426(6) . ? C101 C102 1.375(7) . ? C101 C106 1.389(6) . ? C102 C103 1.384(7) . ? C102 H102 0.9500 . ? C103 C104 1.372(8) . ? C103 H103 0.9500 . ? C104 C105 1.370(8) . ? C104 H104 0.9500 . ? C105 C106 1.382(7) . ? C105 H105 0.9500 . ? C106 H106 0.9500 . ? C107 C108 1.388(6) . ? C107 C112 1.391(6) . ? C108 C109 1.375(7) . ? C108 H108 0.9500 . ? C109 C110 1.383(7) . ? C109 H109 0.9500 . ? C110 C111 1.377(7) . ? C110 H110 0.9500 . ? C111 C112 1.369(7) . ? C111 H111 0.9500 . ? C112 H112 0.9500 . ? C113 C118 1.393(6) . ? C113 C114 1.398(6) . ? C114 C115 1.374(6) . ? C114 H114 0.9500 . ? C115 C116 1.386(6) . ? C115 H115 0.9500 . ? C116 C117 1.398(6) . ? C116 C119 1.453(6) . ? C117 C118 1.374(6) . ? C117 H117 0.9500 . ? C118 H118 0.9500 . ? C119 C120 1.338(6) . ? C119 H119 0.9500 . ? C120 C121 1.464(6) . ? C120 H120 0.9500 . ? C121 C126 1.393(7) . ? C121 C122 1.398(6) . ? C122 C123 1.390(7) . ? C122 H122 0.9500 . ? C123 C124 1.381(7) . ? C123 H123 0.9500 . ? C124 C125 1.380(6) . ? C124 C127 1.478(7) . ? C125 C126 1.371(6) . ? C125 H125 0.9500 . ? C126 H126 0.9500 . ? C127 H127 0.9500 . ? 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 C13 N1 C1 122.0(4) . . ? C13 N1 C7 116.9(4) . . ? C1 N1 C7 120.7(4) . . ? C2 C1 C6 119.1(4) . . ? C2 C1 N1 121.1(4) . . ? C6 C1 N1 119.8(5) . . ? C1 C2 C3 120.5(5) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.9(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.0(5) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.5(5) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.9(5) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 C7 C8 118.2(5) . . ? C12 C7 N1 120.5(4) . . ? C8 C7 N1 121.3(4) . . ? C9 C8 C7 120.5(4) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 119.6(5) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C9 120.4(5) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 120.5(4) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 120.8(5) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C18 C13 C14 118.2(4) . . ? C18 C13 N1 123.2(4) . . ? C14 C13 N1 118.7(5) . . ? C15 C14 C13 120.3(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 121.9(4) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C15 C16 C17 117.5(4) . . ? C15 C16 C19 122.9(4) . . ? C17 C16 C19 119.6(5) . . ? C18 C17 C16 120.9(5) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C13 C18 C17 121.2(4) . . ? C13 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C20 C19 C16 126.0(5) . . ? C20 C19 H19 117.0 . . ? C16 C19 H19 117.0 . . ? C19 C20 C21 128.2(5) . . ? C19 C20 H20 115.9 . . ? C21 C20 H20 115.9 . . ? C22 C21 C26 117.7(4) . . ? C22 C21 C20 119.4(5) . . ? C26 C21 C20 122.9(4) . . ? C23 C22 C21 121.0(5) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 121.3(5) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C23 C24 C25 118.4(4) . . ? C23 C24 C27 119.8(5) . . ? C25 C24 C27 121.7(5) . . ? C26 C25 C24 120.6(5) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C21 120.9(5) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? O1 C27 C24 125.1(5) . . ? O1 C27 H27 117.5 . . ? C24 C27 H27 117.5 . . ? C107 N101 C101 122.8(4) . . ? C107 N101 C113 117.8(4) . . ? C101 N101 C113 119.4(4) . . ? C102 C101 C106 118.9(5) . . ? C102 C101 N101 120.0(5) . . ? C106 C101 N101 121.1(5) . . ? C101 C102 C103 121.1(5) . . ? C101 C102 H102 119.4 . . ? C103 C102 H102 119.4 . . ? C104 C103 C102 120.1(6) . . ? C104 C103 H103 120.0 . . ? C102 C103 H103 120.0 . . ? C105 C104 C103 118.9(5) . . ? C105 C104 H104 120.6 . . ? C103 C104 H104 120.6 . . ? C104 C105 C106 121.8(6) . . ? C104 C105 H105 119.1 . . ? C106 C105 H105 119.1 . . ? C105 C106 C101 119.2(6) . . ? C105 C106 H106 120.4 . . ? C101 C106 H106 120.4 . . ? C108 C107 C112 118.6(5) . . ? C108 C107 N101 121.3(4) . . ? C112 C107 N101 120.0(4) . . ? C109 C108 C107 120.5(5) . . ? C109 C108 H108 119.7 . . ? C107 C108 H108 119.7 . . ? C108 C109 C110 120.5(5) . . ? C108 C109 H109 119.8 . . ? C110 C109 H109 119.8 . . ? C111 C110 C109 118.8(5) . . ? C111 C110 H110 120.6 . . ? C109 C110 H110 120.6 . . ? C112 C111 C110 121.3(5) . . ? C112 C111 H111 119.3 . . ? C110 C111 H111 119.3 . . ? C111 C112 C107 120.1(5) . . ? C111 C112 H112 120.0 . . ? C107 C112 H112 120.0 . . ? C118 C113 C114 118.8(4) . . ? C118 C113 N101 120.4(4) . . ? C114 C113 N101 120.8(4) . . ? C115 C114 C113 120.5(4) . . ? C115 C114 H114 119.8 . . ? C113 C114 H114 119.8 . . ? C114 C115 C116 121.5(4) . . ? C114 C115 H115 119.2 . . ? C116 C115 H115 119.2 . . ? C115 C116 C117 117.3(4) . . ? C115 C116 C119 124.0(4) . . ? C117 C116 C119 118.7(4) . . ? C118 C117 C116 122.2(4) . . ? C118 C117 H117 118.9 . . ? C116 C117 H117 118.9 . . ? C117 C118 C113 119.6(4) . . ? C117 C118 H118 120.2 . . ? C113 C118 H118 120.2 . . ? C120 C119 C116 128.1(4) . . ? C120 C119 H119 116.0 . . ? C116 C119 H119 116.0 . . ? C119 C120 C121 125.7(4) . . ? C119 C120 H120 117.1 . . ? C121 C120 H120 117.1 . . ? C126 C121 C122 118.0(4) . . ? C126 C121 C120 122.6(4) . . ? C122 C121 C120 119.4(4) . . ? C123 C122 C121 120.8(5) . . ? C123 C122 H122 119.6 . . ? C121 C122 H122 119.6 . . ? C124 C123 C122 120.1(4) . . ? C124 C123 H123 120.0 . . ? C122 C123 H123 120.0 . . ? C125 C124 C123 119.2(4) . . ? C125 C124 C127 119.0(5) . . ? C123 C124 C127 121.8(4) . . ? C126 C125 C124 121.2(5) . . ? C126 C125 H125 119.4 . . ? C124 C125 H125 119.4 . . ? C125 C126 C121 120.7(4) . . ? C125 C126 H126 119.7 . . ? C121 C126 H126 119.7 . . ? O101 C127 C124 125.4(5) . . ? O101 C127 H127 117.3 . . ? C124 C127 H127 117.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 N1 C1 C2 -26.1(7) . . . . ? C7 N1 C1 C2 146.8(4) . . . . ? C13 N1 C1 C6 157.1(4) . . . . ? C7 N1 C1 C6 -29.9(6) . . . . ? C6 C1 C2 C3 -1.2(7) . . . . ? N1 C1 C2 C3 -178.1(4) . . . . ? C1 C2 C3 C4 2.3(7) . . . . ? C2 C3 C4 C5 -2.9(8) . . . . ? C3 C4 C5 C6 2.4(8) . . . . ? C4 C5 C6 C1 -1.3(8) . . . . ? C2 C1 C6 C5 0.7(7) . . . . ? N1 C1 C6 C5 177.6(4) . . . . ? C13 N1 C7 C12 -53.7(6) . . . . ? C1 N1 C7 C12 133.0(4) . . . . ? C13 N1 C7 C8 125.0(4) . . . . ? C1 N1 C7 C8 -48.2(6) . . . . ? C12 C7 C8 C9 -0.3(6) . . . . ? N1 C7 C8 C9 -179.1(4) . . . . ? C7 C8 C9 C10 1.1(7) . . . . ? C8 C9 C10 C11 -0.9(7) . . . . ? C9 C10 C11 C12 0.0(7) . . . . ? C10 C11 C12 C7 0.8(7) . . . . ? C8 C7 C12 C11 -0.6(6) . . . . ? N1 C7 C12 C11 178.2(4) . . . . ? C1 N1 C13 C18 -42.2(6) . . . . ? C7 N1 C13 C18 144.6(4) . . . . ? C1 N1 C13 C14 137.7(4) . . . . ? C7 N1 C13 C14 -35.5(6) . . . . ? C18 C13 C14 C15 -1.8(6) . . . . ? N1 C13 C14 C15 178.2(4) . . . . ? C13 C14 C15 C16 0.8(7) . . . . ? C14 C15 C16 C17 1.1(7) . . . . ? C14 C15 C16 C19 -175.6(4) . . . . ? C15 C16 C17 C18 -2.1(6) . . . . ? C19 C16 C17 C18 174.7(4) . . . . ? C14 C13 C18 C17 0.9(7) . . . . ? N1 C13 C18 C17 -179.2(4) . . . . ? C16 C17 C18 C13 1.1(7) . . . . ? C15 C16 C19 C20 11.1(7) . . . . ? C17 C16 C19 C20 -165.5(4) . . . . ? C16 C19 C20 C21 178.7(4) . . . . ? C19 C20 C21 C22 177.6(4) . . . . ? C19 C20 C21 C26 -2.0(7) . . . . ? C26 C21 C22 C23 1.5(7) . . . . ? C20 C21 C22 C23 -178.2(4) . . . . ? C21 C22 C23 C24 -1.3(7) . . . . ? C22 C23 C24 C25 -0.1(7) . . . . ? C22 C23 C24 C27 -178.6(4) . . . . ? C23 C24 C25 C26 1.3(7) . . . . ? C27 C24 C25 C26 179.7(4) . . . . ? C24 C25 C26 C21 -1.1(7) . . . . ? C22 C21 C26 C25 -0.3(7) . . . . ? C20 C21 C26 C25 179.3(4) . . . . ? C23 C24 C27 O1 168.6(5) . . . . ? C25 C24 C27 O1 -9.8(8) . . . . ? C107 N101 C101 C102 149.6(5) . . . . ? C113 N101 C101 C102 -31.4(6) . . . . ? C107 N101 C101 C106 -30.0(6) . . . . ? C113 N101 C101 C106 149.0(4) . . . . ? C106 C101 C102 C103 -1.6(7) . . . . ? N101 C101 C102 C103 178.8(4) . . . . ? C101 C102 C103 C104 2.0(8) . . . . ? C102 C103 C104 C105 -0.6(8) . . . . ? C103 C104 C105 C106 -1.0(8) . . . . ? C104 C105 C106 C101 1.3(7) . . . . ? C102 C101 C106 C105 0.0(7) . . . . ? N101 C101 C106 C105 179.6(4) . . . . ? C101 N101 C107 C108 -35.4(6) . . . . ? C113 N101 C107 C108 145.6(4) . . . . ? C101 N101 C107 C112 146.5(4) . . . . ? C113 N101 C107 C112 -32.4(6) . . . . ? C112 C107 C108 C109 -4.0(6) . . . . ? N101 C107 C108 C109 177.9(4) . . . . ? C107 C108 C109 C110 3.1(7) . . . . ? C108 C109 C110 C111 0.5(7) . . . . ? C109 C110 C111 C112 -3.1(6) . . . . ? C110 C111 C112 C107 2.2(6) . . . . ? C108 C107 C112 C111 1.4(6) . . . . ? N101 C107 C112 C111 179.5(4) . . . . ? C107 N101 C113 C118 128.1(5) . . . . ? C101 N101 C113 C118 -50.9(6) . . . . ? C107 N101 C113 C114 -51.0(6) . . . . ? C101 N101 C113 C114 130.0(5) . . . . ? C118 C113 C114 C115 1.5(7) . . . . ? N101 C113 C114 C115 -179.5(4) . . . . ? C113 C114 C115 C116 -1.8(7) . . . . ? C114 C115 C116 C117 1.7(7) . . . . ? C114 C115 C116 C119 -179.5(5) . . . . ? C115 C116 C117 C118 -1.3(7) . . . . ? C119 C116 C117 C118 179.8(5) . . . . ? C116 C117 C118 C113 1.0(8) . . . . ? C114 C113 C118 C117 -1.1(7) . . . . ? N101 C113 C118 C117 179.9(5) . . . . ? C115 C116 C119 C120 3.3(8) . . . . ? C117 C116 C119 C120 -177.9(5) . . . . ? C116 C119 C120 C121 -177.5(5) . . . . ? C119 C120 C121 C126 8.9(8) . . . . ? C119 C120 C121 C122 -170.8(5) . . . . ? C126 C121 C122 C123 -0.2(7) . . . . ? C120 C121 C122 C123 179.5(5) . . . . ? C121 C122 C123 C124 -0.9(8) . . . . ? C122 C123 C124 C125 1.7(7) . . . . ? C122 C123 C124 C127 -178.3(5) . . . . ? C123 C124 C125 C126 -1.4(7) . . . . ? C127 C124 C125 C126 178.5(5) . . . . ? C124 C125 C126 C121 0.4(7) . . . . ? C122 C121 C126 C125 0.5(7) . . . . ? C120 C121 C126 C125 -179.2(5) . . . . ? C125 C124 C127 O101 179.3(5) . . . . ? C123 C124 C127 O101 -0.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.257 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.066 #===END ################################################################# data_2010src0452_compound_4 _database_code_depnum_ccdc_archive 'CCDC 838486' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H25 N O2' _chemical_formula_sum 'C29 H25 N O2' _chemical_formula_weight 419.50 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2472(4) _cell_length_b 13.4462(4) _cell_length_c 30.0363(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.5670(10) _cell_angle_gamma 90.00 _cell_volume 4542.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 44826 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour Green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9849 _exptl_absorpt_correction_T_max 0.9970 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32084 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7961 _reflns_number_gt 5368 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 for Windows (L. J. Farrugia 1997)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^+6.7595P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7961 _refine_ls_number_parameters 579 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1307 _refine_ls_R_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _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 0.9391(3) 0.9610(3) 0.23028(11) 0.0337(8) Uani 1 1 d . . . C2 C 1.0018(3) 0.8809(3) 0.24815(12) 0.0369(9) Uani 1 1 d . . . H2 H 1.0101 0.8214 0.2314 0.044 Uiso 1 1 calc R . . C3 C 1.0522(3) 0.8879(3) 0.29018(12) 0.0443(10) Uani 1 1 d . . . H3 H 1.0934 0.8323 0.3024 0.053 Uiso 1 1 calc R . . C4 C 1.0435(4) 0.9745(3) 0.31478(12) 0.0484(11) Uani 1 1 d . . . H4 H 1.0793 0.9791 0.3435 0.058 Uiso 1 1 calc R . . C5 C 0.9823(4) 1.0540(3) 0.29698(13) 0.0477(10) Uani 1 1 d . . . H5 H 0.9761 1.1137 0.3137 0.057 Uiso 1 1 calc R . . C6 C 0.9296(3) 1.0483(3) 0.25513(12) 0.0398(9) Uani 1 1 d . . . H6 H 0.8872 1.1036 0.2434 0.048 Uiso 1 1 calc R . . C7 C 0.8579(3) 1.0430(3) 0.16272(11) 0.0332(8) Uani 1 1 d . . . C8 C 0.7420(3) 1.0749(3) 0.16189(13) 0.0444(10) Uani 1 1 d . . . H8 H 0.6829 1.0388 0.1775 0.053 Uiso 1 1 calc R . . C9 C 0.7112(4) 1.1599(3) 0.13823(15) 0.0543(11) Uani 1 1 d . . . H9 H 0.6311 1.1822 0.1379 0.065 Uiso 1 1 calc R . . C10 C 0.7957(4) 1.2116(3) 0.11534(14) 0.0518(11) Uani 1 1 d . . . H10 H 0.7743 1.2694 0.0989 0.062 Uiso 1 1 calc R . . C11 C 0.9112(4) 1.1795(3) 0.11620(13) 0.0495(11) Uani 1 1 d . . . H11 H 0.9700 1.2156 0.1005 0.059 Uiso 1 1 calc R . . C12 C 0.9432(3) 1.0949(3) 0.13982(12) 0.0420(10) Uani 1 1 d . . . H12 H 1.0234 1.0729 0.1402 0.050 Uiso 1 1 calc R . . C13 C 0.8405(3) 0.8640(3) 0.17064(11) 0.0312(8) Uani 1 1 d . . . C14 C 0.8597(3) 0.8352(3) 0.12655(11) 0.0320(8) Uani 1 1 d . . . H14 H 0.9061 0.8762 0.1077 0.038 Uiso 1 1 calc R . . C15 C 0.8121(3) 0.7479(3) 0.11014(12) 0.0322(8) Uani 1 1 d . . . H15 H 0.8262 0.7296 0.0801 0.039 Uiso 1 1 calc R . . C16 C 0.7433(3) 0.6858(3) 0.13701(11) 0.0307(8) Uani 1 1 d . . . C17 C 0.7247(3) 0.7158(3) 0.18075(12) 0.0352(9) Uani 1 1 d . . . H17 H 0.6789 0.6747 0.1997 0.042 Uiso 1 1 calc R . . C18 C 0.7711(3) 0.8037(3) 0.19738(11) 0.0344(9) Uani 1 1 d . . . H18 H 0.7553 0.8229 0.2272 0.041 Uiso 1 1 calc R . . C19 C 0.6885(3) 0.5937(3) 0.12095(12) 0.0323(8) Uani 1 1 d . . . H19 H 0.6565 0.5509 0.1430 0.039 Uiso 1 1 calc R . . C20 C 0.6782(3) 0.5627(3) 0.07853(12) 0.0334(8) Uani 1 1 d . . . H20 H 0.7108 0.6044 0.0562 0.040 Uiso 1 1 calc R . . C21 C 0.6214(3) 0.4708(3) 0.06382(11) 0.0304(8) Uani 1 1 d . . . C22 C 0.6301(3) 0.4412(3) 0.01953(12) 0.0404(9) Uani 1 1 d . . . H22 H 0.6734 0.4815 -0.0006 0.048 Uiso 1 1 calc R . . C23 C 0.5777(3) 0.3548(3) 0.00416(12) 0.0377(9) Uani 1 1 d . . . H23 H 0.5849 0.3366 -0.0262 0.045 Uiso 1 1 calc R . . C24 C 0.5144(3) 0.2947(3) 0.03290(11) 0.0307(8) Uani 1 1 d . . . C25 C 0.5053(3) 0.3231(3) 0.07742(11) 0.0356(9) Uani 1 1 d . . . H25 H 0.4629 0.2822 0.0976 0.043 Uiso 1 1 calc R . . C26 C 0.5570(3) 0.4096(3) 0.09238(12) 0.0353(9) Uani 1 1 d . . . H26 H 0.5487 0.4281 0.1227 0.042 Uiso 1 1 calc R . . C27 C 0.4580(3) 0.1997(3) 0.01900(12) 0.0327(8) Uani 1 1 d . . . C28 C 0.3987(3) 0.0973(3) -0.04133(12) 0.0399(9) Uani 1 1 d . . . H28A H 0.3115 0.0973 -0.0372 0.048 Uiso 1 1 calc R . . H28B H 0.4329 0.0406 -0.0245 0.048 Uiso 1 1 calc R . . C29 C 0.4270(3) 0.0878(3) -0.08967(12) 0.0455(10) Uani 1 1 d . . . H29A H 0.3921 0.1438 -0.1061 0.068 Uiso 1 1 calc R . . H29B H 0.3941 0.0253 -0.1012 0.068 Uiso 1 1 calc R . . H29C H 0.5135 0.0879 -0.0934 0.068 Uiso 1 1 calc R . . N1 N 0.8897(3) 0.9540(2) 0.18694(9) 0.0365(7) Uani 1 1 d . . . O1 O 0.4223(2) 0.13785(19) 0.04484(8) 0.0456(7) Uani 1 1 d . . . O2 O 0.4493(2) 0.19030(17) -0.02519(8) 0.0368(6) Uani 1 1 d . . . C101 C 0.4321(3) 0.9354(3) 0.23388(11) 0.0350(9) Uani 1 1 d . . . C102 C 0.4498(3) 0.8500(3) 0.25966(12) 0.0412(9) Uani 1 1 d . . . H102 H 0.4007 0.7934 0.2550 0.049 Uiso 1 1 calc R . . C103 C 0.5383(4) 0.8475(3) 0.29180(12) 0.0485(11) Uani 1 1 d . . . H103 H 0.5501 0.7885 0.3087 0.058 Uiso 1 1 calc R . . C104 C 0.6100(4) 0.9293(3) 0.29981(13) 0.0484(11) Uani 1 1 d . . . H104 H 0.6720 0.9265 0.3215 0.058 Uiso 1 1 calc R . . C105 C 0.5894(3) 1.0153(3) 0.27554(13) 0.0454(10) Uani 1 1 d . . . H105 H 0.6359 1.0729 0.2814 0.055 Uiso 1 1 calc R . . C106 C 0.5020(3) 1.0182(3) 0.24295(12) 0.0389(9) Uani 1 1 d . . . H106 H 0.4895 1.0777 0.2265 0.047 Uiso 1 1 calc R . . C107 C 0.2927(3) 1.0308(3) 0.18728(11) 0.0320(8) Uani 1 1 d . . . C108 C 0.3110(3) 1.0705(3) 0.14541(12) 0.0362(9) Uani 1 1 d . . . H108 H 0.3574 1.0352 0.1244 0.043 Uiso 1 1 calc R . . C109 C 0.2619(3) 1.1616(3) 0.13400(13) 0.0392(9) Uani 1 1 d . . . H109 H 0.2742 1.1884 0.1051 0.047 Uiso 1 1 calc R . . C110 C 0.1949(3) 1.2136(3) 0.16460(13) 0.0403(9) Uani 1 1 d . . . H110 H 0.1620 1.2765 0.1570 0.048 Uiso 1 1 calc R . . C111 C 0.1762(3) 1.1734(3) 0.20633(13) 0.0415(10) Uani 1 1 d . . . H111 H 0.1298 1.2086 0.2274 0.050 Uiso 1 1 calc R . . C112 C 0.2246(3) 1.0827(3) 0.21748(12) 0.0367(9) Uani 1 1 d . . . H112 H 0.2110 1.0554 0.2462 0.044 Uiso 1 1 calc R . . C113 C 0.3174(3) 0.8524(2) 0.17408(11) 0.0304(8) Uani 1 1 d . . . C114 C 0.2022(3) 0.8383(3) 0.15744(11) 0.0319(8) Uani 1 1 d . . . H114 H 0.1428 0.8869 0.1629 0.038 Uiso 1 1 calc R . . C115 C 0.1739(3) 0.7548(3) 0.13319(11) 0.0323(8) Uani 1 1 d . . . H115 H 0.0948 0.7466 0.1224 0.039 Uiso 1 1 calc R . . C116 C 0.2588(3) 0.6816(3) 0.12392(11) 0.0304(8) Uani 1 1 d . . . C117 C 0.3740(3) 0.6981(3) 0.13935(11) 0.0343(9) Uani 1 1 d . . . H117 H 0.4341 0.6508 0.1328 0.041 Uiso 1 1 calc R . . C118 C 0.4035(3) 0.7813(3) 0.16389(11) 0.0338(9) Uani 1 1 d . . . H118 H 0.4831 0.7904 0.1740 0.041 Uiso 1 1 calc R . . C119 C 0.2319(3) 0.5895(3) 0.09974(11) 0.0322(8) Uani 1 1 d . . . H119 H 0.2976 0.5481 0.0928 0.039 Uiso 1 1 calc R . . C120 C 0.1252(3) 0.5577(3) 0.08640(11) 0.0331(8) Uani 1 1 d . . . H120 H 0.0597 0.5998 0.0928 0.040 Uiso 1 1 calc R . . C121 C 0.0979(3) 0.4649(3) 0.06301(11) 0.0301(8) Uani 1 1 d . . . C122 C -0.0187(3) 0.4457(3) 0.04940(11) 0.0342(8) Uani 1 1 d . . . H122 H -0.0791 0.4927 0.0560 0.041 Uiso 1 1 calc R . . C123 C -0.0485(3) 0.3600(3) 0.02650(11) 0.0326(8) Uani 1 1 d . . . H123 H -0.1288 0.3485 0.0178 0.039 Uiso 1 1 calc R . . C124 C 0.0383(3) 0.2909(3) 0.01624(11) 0.0305(8) Uani 1 1 d . . . C125 C 0.1553(3) 0.3083(3) 0.02990(11) 0.0334(8) Uani 1 1 d . . . H125 H 0.2154 0.2610 0.0232 0.040 Uiso 1 1 calc R . . C126 C 0.1845(3) 0.3939(3) 0.05312(11) 0.0329(8) Uani 1 1 d . . . H126 H 0.2644 0.4046 0.0625 0.040 Uiso 1 1 calc R . . C127 C 0.0111(3) 0.1957(3) -0.00723(11) 0.0323(8) Uani 1 1 d . . . C128 C -0.1422(3) 0.0890(3) -0.03283(13) 0.0418(10) Uani 1 1 d . . . H12A H -0.1143 0.0338 -0.0136 0.050 Uiso 1 1 calc R . . H12B H -0.1097 0.0796 -0.0631 0.050 Uiso 1 1 calc R . . C129 C -0.2749(3) 0.0924(3) -0.03442(14) 0.0462(10) Uani 1 1 d . . . H12C H -0.3053 0.1042 -0.0044 0.069 Uiso 1 1 calc R . . H12D H -0.3056 0.0289 -0.0457 0.069 Uiso 1 1 calc R . . H12E H -0.3008 0.1463 -0.0542 0.069 Uiso 1 1 calc R . . N101 N 0.3448(3) 0.9375(2) 0.19958(9) 0.0356(7) Uani 1 1 d . . . O101 O 0.0857(2) 0.13549(19) -0.01773(8) 0.0417(6) Uani 1 1 d . . . O102 O -0.1048(2) 0.18475(17) -0.01445(8) 0.0394(6) 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 0.036(2) 0.039(2) 0.0262(18) 0.0054(17) 0.0022(16) -0.0086(17) C2 0.039(2) 0.038(2) 0.033(2) 0.0042(17) 0.0040(17) -0.0084(18) C3 0.044(2) 0.054(3) 0.035(2) 0.012(2) -0.0035(18) -0.006(2) C4 0.052(3) 0.072(3) 0.0215(19) -0.002(2) -0.0019(18) -0.010(2) C5 0.052(3) 0.055(3) 0.036(2) -0.007(2) 0.011(2) -0.005(2) C6 0.044(2) 0.047(2) 0.029(2) 0.0034(18) 0.0039(17) -0.0003(19) C7 0.042(2) 0.034(2) 0.0237(18) 0.0004(16) -0.0013(16) -0.0044(18) C8 0.037(2) 0.048(2) 0.048(2) 0.006(2) 0.0072(19) -0.0021(19) C9 0.048(3) 0.052(3) 0.063(3) 0.002(2) 0.002(2) 0.013(2) C10 0.062(3) 0.040(2) 0.054(3) 0.011(2) -0.011(2) 0.001(2) C11 0.052(3) 0.052(3) 0.045(2) 0.017(2) -0.001(2) -0.011(2) C12 0.041(2) 0.043(2) 0.042(2) 0.0085(19) -0.0037(18) -0.0070(19) C13 0.0304(19) 0.031(2) 0.0325(19) 0.0059(16) -0.0016(16) -0.0014(16) C14 0.0314(19) 0.033(2) 0.0313(19) 0.0035(16) 0.0043(16) -0.0040(16) C15 0.0303(19) 0.035(2) 0.0316(19) -0.0019(17) 0.0043(16) 0.0023(16) C16 0.0302(19) 0.031(2) 0.0307(19) 0.0017(16) 0.0004(16) 0.0005(16) C17 0.035(2) 0.039(2) 0.032(2) 0.0065(17) 0.0021(16) -0.0006(17) C18 0.042(2) 0.038(2) 0.0237(18) -0.0012(16) -0.0010(16) 0.0003(18) C19 0.0303(19) 0.031(2) 0.036(2) 0.0025(17) 0.0043(16) 0.0014(16) C20 0.033(2) 0.031(2) 0.036(2) 0.0026(17) 0.0068(16) -0.0014(16) C21 0.0284(19) 0.0308(19) 0.0322(19) 0.0000(16) 0.0013(16) 0.0019(16) C22 0.047(2) 0.037(2) 0.037(2) -0.0010(18) 0.0093(18) -0.0061(19) C23 0.045(2) 0.037(2) 0.032(2) -0.0046(17) 0.0090(17) -0.0012(18) C24 0.0262(18) 0.031(2) 0.0353(19) 0.0020(16) 0.0021(16) -0.0003(16) C25 0.036(2) 0.041(2) 0.0298(19) 0.0058(17) 0.0064(16) -0.0042(18) C26 0.036(2) 0.040(2) 0.0298(19) -0.0025(17) 0.0047(16) -0.0035(18) C27 0.0274(19) 0.037(2) 0.034(2) 0.0007(18) 0.0043(16) 0.0032(16) C28 0.041(2) 0.037(2) 0.042(2) 0.0005(18) -0.0012(18) -0.0045(18) C29 0.045(2) 0.052(3) 0.040(2) -0.006(2) 0.0006(19) -0.002(2) N1 0.0467(19) 0.0326(17) 0.0302(16) 0.0042(14) -0.0071(14) -0.0065(15) O1 0.0579(18) 0.0406(16) 0.0386(15) 0.0007(13) 0.0075(13) -0.0132(14) O2 0.0438(15) 0.0319(14) 0.0347(14) -0.0003(11) -0.0010(12) -0.0039(12) C101 0.038(2) 0.039(2) 0.0281(19) -0.0077(17) 0.0066(16) 0.0030(18) C102 0.048(2) 0.044(2) 0.031(2) -0.0025(18) -0.0021(18) -0.0035(19) C103 0.057(3) 0.058(3) 0.031(2) -0.002(2) -0.0007(19) 0.005(2) C104 0.043(2) 0.070(3) 0.033(2) -0.014(2) -0.0016(18) 0.009(2) C105 0.040(2) 0.054(3) 0.042(2) -0.016(2) 0.0031(19) -0.003(2) C106 0.042(2) 0.042(2) 0.033(2) -0.0036(18) 0.0042(18) 0.0028(18) C107 0.038(2) 0.031(2) 0.0275(18) -0.0039(16) 0.0003(16) -0.0037(17) C108 0.038(2) 0.037(2) 0.034(2) -0.0053(17) 0.0079(17) 0.0013(17) C109 0.036(2) 0.038(2) 0.044(2) 0.0043(19) 0.0041(18) -0.0059(18) C110 0.039(2) 0.029(2) 0.053(2) -0.0017(19) -0.0044(19) 0.0011(17) C111 0.041(2) 0.042(2) 0.041(2) -0.0129(19) 0.0035(18) 0.0050(19) C112 0.038(2) 0.041(2) 0.0310(19) -0.0066(17) 0.0012(17) -0.0007(18) C113 0.037(2) 0.0260(19) 0.0283(18) -0.0035(15) 0.0019(16) -0.0025(16) C114 0.032(2) 0.028(2) 0.035(2) 0.0030(16) 0.0075(16) 0.0033(16) C115 0.031(2) 0.032(2) 0.033(2) 0.0046(17) 0.0019(16) -0.0005(16) C116 0.033(2) 0.0295(19) 0.0283(18) 0.0039(16) 0.0015(15) -0.0029(16) C117 0.040(2) 0.030(2) 0.033(2) -0.0003(16) 0.0027(17) 0.0047(17) C118 0.031(2) 0.039(2) 0.0317(19) 0.0017(17) 0.0040(16) 0.0003(17) C119 0.036(2) 0.033(2) 0.0271(18) -0.0006(16) 0.0052(16) 0.0024(17) C120 0.037(2) 0.036(2) 0.0266(18) 0.0014(16) 0.0034(16) 0.0034(17) C121 0.039(2) 0.031(2) 0.0211(17) 0.0049(15) 0.0005(15) -0.0048(17) C122 0.038(2) 0.032(2) 0.0323(19) 0.0004(17) 0.0011(17) 0.0056(17) C123 0.035(2) 0.033(2) 0.0298(19) 0.0048(16) 0.0015(16) -0.0006(17) C124 0.035(2) 0.031(2) 0.0248(17) 0.0052(15) 0.0021(15) -0.0012(16) C125 0.037(2) 0.031(2) 0.0324(19) 0.0014(17) 0.0051(16) 0.0066(17) C126 0.031(2) 0.035(2) 0.033(2) 0.0025(17) 0.0013(16) 0.0011(17) C127 0.038(2) 0.029(2) 0.0306(19) 0.0056(16) 0.0019(16) -0.0001(18) C128 0.049(2) 0.027(2) 0.049(2) -0.0047(18) -0.003(2) -0.0047(18) C129 0.045(2) 0.040(2) 0.054(3) -0.003(2) -0.002(2) -0.0105(19) N101 0.0431(18) 0.0293(17) 0.0344(17) -0.0005(14) -0.0039(14) 0.0014(14) O101 0.0439(16) 0.0367(15) 0.0445(16) -0.0071(13) 0.0049(13) 0.0003(13) O102 0.0343(14) 0.0322(14) 0.0515(16) -0.0045(12) -0.0049(12) 0.0004(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.392(5) . ? C1 C6 1.396(5) . ? C1 N1 1.413(4) . ? C2 C3 1.382(5) . ? C2 H2 0.9500 . ? C3 C4 1.384(6) . ? C3 H3 0.9500 . ? C4 C5 1.376(6) . ? C4 H4 0.9500 . ? C5 C6 1.387(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.372(5) . ? C7 C12 1.377(5) . ? C7 N1 1.443(4) . ? C8 C9 1.388(5) . ? C8 H8 0.9500 . ? C9 C10 1.368(6) . ? C9 H9 0.9500 . ? C10 C11 1.369(6) . ? C10 H10 0.9500 . ? C11 C12 1.386(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.387(5) . ? C13 C14 1.399(5) . ? C13 N1 1.417(4) . ? C14 C15 1.379(5) . ? C14 H14 0.9500 . ? C15 C16 1.399(5) . ? C15 H15 0.9500 . ? C16 C17 1.392(5) . ? C16 C19 1.464(5) . ? C17 C18 1.383(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.344(5) . ? C19 H19 0.9500 . ? C20 C21 1.458(5) . ? C20 H20 0.9500 . ? C21 C22 1.393(5) . ? C21 C26 1.397(5) . ? C22 C23 1.380(5) . ? C22 H22 0.9500 . ? C23 C24 1.384(5) . ? C23 H23 0.9500 . ? C24 C25 1.395(5) . ? C24 C27 1.485(5) . ? C25 C26 1.374(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O1 1.209(4) . ? C27 O2 1.336(4) . ? C28 O2 1.455(4) . ? C28 C29 1.495(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C101 C106 1.389(5) . ? C101 C102 1.398(5) . ? C101 N101 1.416(4) . ? C102 C103 1.380(5) . ? C102 H102 0.9500 . ? C103 C104 1.384(6) . ? C103 H103 0.9500 . ? C104 C105 1.386(6) . ? C104 H104 0.9500 . ? C105 C106 1.381(5) . ? C105 H105 0.9500 . ? C106 H106 0.9500 . ? C107 C112 1.382(5) . ? C107 C108 1.384(5) . ? C107 N101 1.432(4) . ? C108 C109 1.385(5) . ? C108 H108 0.9500 . ? C109 C110 1.383(5) . ? C109 H109 0.9500 . ? C110 C111 1.383(5) . ? C110 H110 0.9500 . ? C111 C112 1.376(5) . ? C111 H111 0.9500 . ? C112 H112 0.9500 . ? C113 C118 1.397(5) . ? C113 C114 1.397(5) . ? C113 N101 1.410(4) . ? C114 C115 1.373(5) . ? C114 H114 0.9500 . ? C115 C116 1.402(5) . ? C115 H115 0.9500 . ? C116 C117 1.390(5) . ? C116 C119 1.465(5) . ? C117 C118 1.378(5) . ? C117 H117 0.9500 . ? C118 H118 0.9500 . ? C119 C120 1.332(5) . ? C119 H119 0.9500 . ? C120 C121 1.462(5) . ? C120 H120 0.9500 . ? C121 C122 1.394(5) . ? C121 C126 1.398(5) . ? C122 C123 1.381(5) . ? C122 H122 0.9500 . ? C123 C124 1.385(5) . ? C123 H123 0.9500 . ? C124 C125 1.395(5) . ? C124 C127 1.492(5) . ? C125 C126 1.384(5) . ? C125 H125 0.9500 . ? C126 H126 0.9500 . ? C127 O101 1.210(4) . ? C127 O102 1.327(4) . ? C128 O102 1.460(4) . ? C128 C129 1.493(5) . ? C128 H12A 0.9900 . ? C128 H12B 0.9900 . ? C129 H12C 0.9800 . ? C129 H12D 0.9800 . ? C129 H12E 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.0(3) . . ? C2 C1 N1 119.8(3) . . ? C6 C1 N1 121.1(3) . . ? C3 C2 C1 120.1(4) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.9(4) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.9(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.1(4) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 119.8(4) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C8 C7 C12 119.9(3) . . ? C8 C7 N1 120.0(3) . . ? C12 C7 N1 120.1(3) . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.3(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.6(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.6(4) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C7 C12 C11 119.6(4) . . ? C7 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C18 C13 C14 118.7(3) . . ? C18 C13 N1 121.3(3) . . ? C14 C13 N1 120.0(3) . . ? C15 C14 C13 120.7(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 121.1(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 117.4(3) . . ? C17 C16 C19 119.3(3) . . ? C15 C16 C19 123.2(3) . . ? C18 C17 C16 121.9(3) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C17 C18 C13 120.1(3) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? C20 C19 C16 127.3(3) . . ? C20 C19 H19 116.3 . . ? C16 C19 H19 116.3 . . ? C19 C20 C21 125.7(3) . . ? C19 C20 H20 117.2 . . ? C21 C20 H20 117.2 . . ? C22 C21 C26 117.4(3) . . ? C22 C21 C20 119.8(3) . . ? C26 C21 C20 122.8(3) . . ? C23 C22 C21 121.8(3) . . ? C23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C22 C23 C24 120.2(3) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C25 118.8(3) . . ? C23 C24 C27 123.2(3) . . ? C25 C24 C27 118.0(3) . . ? C26 C25 C24 120.7(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C21 121.2(3) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? O1 C27 O2 123.5(3) . . ? O1 C27 C24 123.7(3) . . ? O2 C27 C24 112.8(3) . . ? O2 C28 C29 108.1(3) . . ? O2 C28 H28A 110.1 . . ? C29 C28 H28A 110.1 . . ? O2 C28 H28B 110.1 . . ? C29 C28 H28B 110.1 . . ? H28A C28 H28B 108.4 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C1 N1 C13 121.6(3) . . ? C1 N1 C7 120.2(3) . . ? C13 N1 C7 116.1(3) . . ? C27 O2 C28 115.9(3) . . ? C106 C101 C102 118.2(3) . . ? C106 C101 N101 120.9(3) . . ? C102 C101 N101 120.9(3) . . ? C103 C102 C101 120.4(4) . . ? C103 C102 H102 119.8 . . ? C101 C102 H102 119.8 . . ? C102 C103 C104 121.1(4) . . ? C102 C103 H103 119.4 . . ? C104 C103 H103 119.4 . . ? C103 C104 C105 118.6(4) . . ? C103 C104 H104 120.7 . . ? C105 C104 H104 120.7 . . ? C106 C105 C104 120.7(4) . . ? C106 C105 H105 119.7 . . ? C104 C105 H105 119.7 . . ? C105 C106 C101 121.0(4) . . ? C105 C106 H106 119.5 . . ? C101 C106 H106 119.5 . . ? C112 C107 C108 119.4(3) . . ? C112 C107 N101 120.1(3) . . ? C108 C107 N101 120.6(3) . . ? C107 C108 C109 120.2(3) . . ? C107 C108 H108 119.9 . . ? C109 C108 H108 119.9 . . ? C110 C109 C108 120.0(4) . . ? C110 C109 H109 120.0 . . ? C108 C109 H109 120.0 . . ? C111 C110 C109 119.6(4) . . ? C111 C110 H110 120.2 . . ? C109 C110 H110 120.2 . . ? C112 C111 C110 120.2(4) . . ? C112 C111 H111 119.9 . . ? C110 C111 H111 119.9 . . ? C111 C112 C107 120.5(4) . . ? C111 C112 H112 119.7 . . ? C107 C112 H112 119.7 . . ? C118 C113 C114 118.1(3) . . ? C118 C113 N101 121.8(3) . . ? C114 C113 N101 120.1(3) . . ? C115 C114 C113 120.7(3) . . ? C115 C114 H114 119.7 . . ? C113 C114 H114 119.7 . . ? C114 C115 C116 121.7(3) . . ? C114 C115 H115 119.2 . . ? C116 C115 H115 119.2 . . ? C117 C116 C115 117.1(3) . . ? C117 C116 C119 119.2(3) . . ? C115 C116 C119 123.7(3) . . ? C118 C117 C116 121.8(3) . . ? C118 C117 H117 119.1 . . ? C116 C117 H117 119.1 . . ? C117 C118 C113 120.6(3) . . ? C117 C118 H118 119.7 . . ? C113 C118 H118 119.7 . . ? C120 C119 C116 127.0(3) . . ? C120 C119 H119 116.5 . . ? C116 C119 H119 116.5 . . ? C119 C120 C121 127.1(3) . . ? C119 C120 H120 116.5 . . ? C121 C120 H120 116.5 . . ? C122 C121 C126 117.8(3) . . ? C122 C121 C120 119.4(3) . . ? C126 C121 C120 122.8(3) . . ? C123 C122 C121 121.6(3) . . ? C123 C122 H122 119.2 . . ? C121 C122 H122 119.2 . . ? C122 C123 C124 120.2(3) . . ? C122 C123 H123 119.9 . . ? C124 C123 H123 119.9 . . ? C123 C124 C125 119.2(3) . . ? C123 C124 C127 122.7(3) . . ? C125 C124 C127 118.1(3) . . ? C126 C125 C124 120.4(3) . . ? C126 C125 H125 119.8 . . ? C124 C125 H125 119.8 . . ? C125 C126 C121 120.9(3) . . ? C125 C126 H126 119.6 . . ? C121 C126 H126 119.6 . . ? O101 C127 O102 124.5(3) . . ? O101 C127 C124 123.9(3) . . ? O102 C127 C124 111.6(3) . . ? O102 C128 C129 105.6(3) . . ? O102 C128 H12A 110.6 . . ? C129 C128 H12A 110.6 . . ? O102 C128 H12B 110.6 . . ? C129 C128 H12B 110.6 . . ? H12A C128 H12B 108.7 . . ? C128 C129 H12C 109.5 . . ? C128 C129 H12D 109.5 . . ? H12C C129 H12D 109.5 . . ? C128 C129 H12E 109.5 . . ? H12C C129 H12E 109.5 . . ? H12D C129 H12E 109.5 . . ? C113 N101 C101 121.7(3) . . ? C113 N101 C107 119.0(3) . . ? C101 N101 C107 119.0(3) . . ? C127 O102 C128 116.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.0(5) . . . . ? N1 C1 C2 C3 178.8(3) . . . . ? C1 C2 C3 C4 -1.4(6) . . . . ? C2 C3 C4 C5 0.8(6) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? C4 C5 C6 C1 -0.4(6) . . . . ? C2 C1 C6 C5 -0.1(5) . . . . ? N1 C1 C6 C5 -177.9(3) . . . . ? C12 C7 C8 C9 -0.5(6) . . . . ? N1 C7 C8 C9 -179.4(3) . . . . ? C7 C8 C9 C10 0.6(6) . . . . ? C8 C9 C10 C11 -0.6(7) . . . . ? C9 C10 C11 C12 0.4(6) . . . . ? C8 C7 C12 C11 0.3(6) . . . . ? N1 C7 C12 C11 179.2(3) . . . . ? C10 C11 C12 C7 -0.2(6) . . . . ? C18 C13 C14 C15 -0.9(5) . . . . ? N1 C13 C14 C15 -179.8(3) . . . . ? C13 C14 C15 C16 0.0(5) . . . . ? C14 C15 C16 C17 0.2(5) . . . . ? C14 C15 C16 C19 178.5(3) . . . . ? C15 C16 C17 C18 0.5(5) . . . . ? C19 C16 C17 C18 -177.9(3) . . . . ? C16 C17 C18 C13 -1.4(5) . . . . ? C14 C13 C18 C17 1.6(5) . . . . ? N1 C13 C18 C17 -179.5(3) . . . . ? C17 C16 C19 C20 166.8(4) . . . . ? C15 C16 C19 C20 -11.5(6) . . . . ? C16 C19 C20 C21 -179.2(3) . . . . ? C19 C20 C21 C22 -171.7(4) . . . . ? C19 C20 C21 C26 8.4(6) . . . . ? C26 C21 C22 C23 0.0(5) . . . . ? C20 C21 C22 C23 -179.9(3) . . . . ? C21 C22 C23 C24 -0.2(6) . . . . ? C22 C23 C24 C25 -0.1(5) . . . . ? C22 C23 C24 C27 -178.6(3) . . . . ? C23 C24 C25 C26 0.7(5) . . . . ? C27 C24 C25 C26 179.2(3) . . . . ? C24 C25 C26 C21 -0.9(5) . . . . ? C22 C21 C26 C25 0.6(5) . . . . ? C20 C21 C26 C25 -179.5(3) . . . . ? C23 C24 C27 O1 165.6(4) . . . . ? C25 C24 C27 O1 -12.9(5) . . . . ? C23 C24 C27 O2 -15.3(5) . . . . ? C25 C24 C27 O2 166.3(3) . . . . ? C2 C1 N1 C13 36.7(5) . . . . ? C6 C1 N1 C13 -145.6(3) . . . . ? C2 C1 N1 C7 -160.7(3) . . . . ? C6 C1 N1 C7 17.1(5) . . . . ? C18 C13 N1 C1 41.1(5) . . . . ? C14 C13 N1 C1 -140.0(3) . . . . ? C18 C13 N1 C7 -122.2(4) . . . . ? C14 C13 N1 C7 56.6(4) . . . . ? C8 C7 N1 C1 -98.4(4) . . . . ? C12 C7 N1 C1 82.7(4) . . . . ? C8 C7 N1 C13 65.2(4) . . . . ? C12 C7 N1 C13 -113.7(4) . . . . ? O1 C27 O2 C28 -3.0(5) . . . . ? C24 C27 O2 C28 177.9(3) . . . . ? C29 C28 O2 C27 -164.3(3) . . . . ? C106 C101 C102 C103 -2.9(5) . . . . ? N101 C101 C102 C103 177.4(3) . . . . ? C101 C102 C103 C104 1.0(6) . . . . ? C102 C103 C104 C105 1.6(6) . . . . ? C103 C104 C105 C106 -2.3(6) . . . . ? C104 C105 C106 C101 0.4(6) . . . . ? C102 C101 C106 C105 2.2(5) . . . . ? N101 C101 C106 C105 -178.1(3) . . . . ? C112 C107 C108 C109 0.3(5) . . . . ? N101 C107 C108 C109 -178.9(3) . . . . ? C107 C108 C109 C110 0.5(5) . . . . ? C108 C109 C110 C111 -0.8(5) . . . . ? C109 C110 C111 C112 0.5(6) . . . . ? C110 C111 C112 C107 0.3(6) . . . . ? C108 C107 C112 C111 -0.7(5) . . . . ? N101 C107 C112 C111 178.6(3) . . . . ? C118 C113 C114 C115 2.4(5) . . . . ? N101 C113 C114 C115 -178.9(3) . . . . ? C113 C114 C115 C116 -0.6(5) . . . . ? C114 C115 C116 C117 -1.6(5) . . . . ? C114 C115 C116 C119 177.5(3) . . . . ? C115 C116 C117 C118 1.9(5) . . . . ? C119 C116 C117 C118 -177.3(3) . . . . ? C116 C117 C118 C113 0.0(5) . . . . ? C114 C113 C118 C117 -2.1(5) . . . . ? N101 C113 C118 C117 179.2(3) . . . . ? C117 C116 C119 C120 173.3(3) . . . . ? C115 C116 C119 C120 -5.9(6) . . . . ? C116 C119 C120 C121 -178.7(3) . . . . ? C119 C120 C121 C122 -176.6(3) . . . . ? C119 C120 C121 C126 2.8(5) . . . . ? C126 C121 C122 C123 -0.6(5) . . . . ? C120 C121 C122 C123 178.8(3) . . . . ? C121 C122 C123 C124 -0.4(5) . . . . ? C122 C123 C124 C125 1.0(5) . . . . ? C122 C123 C124 C127 178.2(3) . . . . ? C123 C124 C125 C126 -0.5(5) . . . . ? C127 C124 C125 C126 -177.8(3) . . . . ? C124 C125 C126 C121 -0.6(5) . . . . ? C122 C121 C126 C125 1.1(5) . . . . ? C120 C121 C126 C125 -178.3(3) . . . . ? C123 C124 C127 O101 177.7(3) . . . . ? C125 C124 C127 O101 -5.0(5) . . . . ? C123 C124 C127 O102 -3.3(5) . . . . ? C125 C124 C127 O102 174.0(3) . . . . ? C118 C113 N101 C101 -32.9(5) . . . . ? C114 C113 N101 C101 148.5(3) . . . . ? C118 C113 N101 C107 140.1(3) . . . . ? C114 C113 N101 C107 -38.5(5) . . . . ? C106 C101 N101 C113 146.4(3) . . . . ? C102 C101 N101 C113 -33.9(5) . . . . ? C106 C101 N101 C107 -26.6(5) . . . . ? C102 C101 N101 C107 153.1(3) . . . . ? C112 C107 N101 C113 122.2(4) . . . . ? C108 C107 N101 C113 -58.5(5) . . . . ? C112 C107 N101 C101 -64.6(4) . . . . ? C108 C107 N101 C101 114.7(4) . . . . ? O101 C127 O102 C128 5.5(5) . . . . ? C124 C127 O102 C128 -173.5(3) . . . . ? C129 C128 O102 C127 175.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.262 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.056 #===END ################################################################# data_2010src0522_compound_6 _database_code_depnum_ccdc_archive 'CCDC 838487' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H21 N O2' _chemical_formula_sum 'C27 H21 N O2' _chemical_formula_weight 391.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.1248(5) _cell_length_b 9.6815(2) _cell_length_c 12.9988(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.727(2) _cell_angle_gamma 90.00 _cell_volume 2015.63(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 37097 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour 'Light Yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28268 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4613 _reflns_number_gt 3640 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (L. J. Farrugia 1997)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0417P)^2^+0.9001P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4613 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.32642(9) -0.01006(15) 0.06354(12) 0.0209(3) Uani 1 1 d . . . C2 C 0.35337(10) -0.14533(16) 0.09065(13) 0.0254(3) Uani 1 1 d . . . H2 H 0.3773 -0.1723 0.1656 0.030 Uiso 1 1 calc R . . C3 C 0.34514(11) -0.24026(16) 0.00803(13) 0.0283(4) Uani 1 1 d . . . H3 H 0.3628 -0.3330 0.0264 0.034 Uiso 1 1 calc R . . C4 C 0.31135(10) -0.20105(16) -0.10140(13) 0.0257(3) Uani 1 1 d . . . H4 H 0.3065 -0.2663 -0.1579 0.031 Uiso 1 1 calc R . . C5 C 0.28471(10) -0.06655(16) -0.12807(12) 0.0248(3) Uani 1 1 d . . . H5 H 0.2613 -0.0396 -0.2031 0.030 Uiso 1 1 calc R . . C6 C 0.29194(10) 0.02905(16) -0.04601(12) 0.0234(3) Uani 1 1 d . . . H6 H 0.2733 0.1212 -0.0647 0.028 Uiso 1 1 calc R . . C7 C 0.37958(9) 0.21065(15) 0.15551(11) 0.0207(3) Uani 1 1 d . . . C8 C 0.44351(10) 0.21390(16) 0.11149(12) 0.0244(3) Uani 1 1 d . . . H8 H 0.4570 0.1328 0.0802 0.029 Uiso 1 1 calc R . . C9 C 0.48708(10) 0.33522(17) 0.11360(13) 0.0271(3) Uani 1 1 d . . . H9 H 0.5294 0.3368 0.0821 0.033 Uiso 1 1 calc R . . C10 C 0.46996(10) 0.45381(17) 0.16077(13) 0.0276(4) Uani 1 1 d . . . H10 H 0.5005 0.5362 0.1624 0.033 Uiso 1 1 calc R . . C11 C 0.40754(10) 0.45102(16) 0.20571(12) 0.0254(3) Uani 1 1 d . . . H11 H 0.3959 0.5318 0.2392 0.030 Uiso 1 1 calc R . . C12 C 0.36198(10) 0.33120(16) 0.20211(12) 0.0226(3) Uani 1 1 d . . . H12 H 0.3185 0.3313 0.2316 0.027 Uiso 1 1 calc R . . C13 C 0.28983(9) 0.05909(15) 0.22132(11) 0.0200(3) Uani 1 1 d . . . C14 C 0.32091(9) 0.10211(15) 0.33128(12) 0.0210(3) Uani 1 1 d . . . H14 H 0.3730 0.1488 0.3591 0.025 Uiso 1 1 calc R . . C15 C 0.27638(9) 0.07717(15) 0.39945(12) 0.0207(3) Uani 1 1 d . . . H15 H 0.2979 0.1093 0.4732 0.025 Uiso 1 1 calc R . . C16 C 0.20040(9) 0.00585(15) 0.36309(12) 0.0212(3) Uani 1 1 d . . . C17 C 0.17243(9) -0.04343(15) 0.25537(12) 0.0220(3) Uani 1 1 d . . . H17 H 0.1227 -0.0968 0.2296 0.026 Uiso 1 1 calc R . . C18 C 0.21531(9) -0.01666(15) 0.18458(12) 0.0213(3) Uani 1 1 d . . . H18 H 0.1940 -0.0498 0.1111 0.026 Uiso 1 1 calc R . . C19 C 0.15399(9) -0.01848(16) 0.43731(12) 0.0231(3) Uani 1 1 d . . . H19 H 0.1200 -0.0986 0.4265 0.028 Uiso 1 1 calc R . . C20 C 0.15760(9) 0.06752(16) 0.51940(12) 0.0224(3) Uani 1 1 d . . . H20 H 0.1874 0.1510 0.5222 0.027 Uiso 1 1 calc R . . C21 C 0.12168(9) 0.05012(15) 0.60560(12) 0.0214(3) Uani 1 1 d . . . C22 C 0.12633(9) 0.16136(15) 0.67621(12) 0.0227(3) Uani 1 1 d . . . H22 H 0.1485 0.2469 0.6635 0.027 Uiso 1 1 calc R . . C23 C 0.09929(9) 0.14907(15) 0.76410(12) 0.0221(3) Uani 1 1 d . . . H23 H 0.1022 0.2262 0.8105 0.027 Uiso 1 1 calc R . . C24 C 0.06775(9) 0.02371(15) 0.78471(12) 0.0209(3) Uani 1 1 d . . . C25 C 0.06103(10) -0.08736(16) 0.71371(13) 0.0239(3) Uani 1 1 d . . . H25 H 0.0384 -0.1725 0.7264 0.029 Uiso 1 1 calc R . . C26 C 0.08715(10) -0.07430(16) 0.62479(12) 0.0239(3) Uani 1 1 d . . . H26 H 0.0816 -0.1502 0.5764 0.029 Uiso 1 1 calc R . . C27 C 0.04180(9) 0.01155(15) 0.88123(12) 0.0218(3) Uani 1 1 d . . . N1 N 0.33331(8) 0.08781(13) 0.14923(10) 0.0228(3) Uani 1 1 d . . . O1 O 0.03574(7) 0.11631(11) 0.93400(9) 0.0284(3) Uani 1 1 d . . . O2 O 0.02571(8) -0.11214(11) 0.90667(9) 0.0302(3) Uani 1 1 d . . . H2A H 0.0065 -0.1078 0.9578 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0256(8) 0.0191(7) 0.0204(7) -0.0023(6) 0.0110(6) -0.0014(6) C2 0.0349(9) 0.0210(8) 0.0204(7) 0.0013(6) 0.0100(6) 0.0021(6) C3 0.0372(10) 0.0183(7) 0.0295(8) -0.0014(6) 0.0119(7) 0.0013(7) C4 0.0298(8) 0.0250(8) 0.0244(8) -0.0079(6) 0.0120(6) -0.0045(7) C5 0.0293(8) 0.0269(8) 0.0185(7) 0.0003(6) 0.0088(6) -0.0034(6) C6 0.0283(8) 0.0189(7) 0.0239(7) 0.0020(6) 0.0103(6) 0.0003(6) C7 0.0252(8) 0.0188(7) 0.0174(7) 0.0016(6) 0.0067(6) -0.0002(6) C8 0.0267(8) 0.0254(8) 0.0213(7) 0.0012(6) 0.0087(6) 0.0041(6) C9 0.0216(8) 0.0362(9) 0.0242(8) 0.0022(7) 0.0089(6) -0.0023(7) C10 0.0279(8) 0.0251(8) 0.0272(8) 0.0026(7) 0.0067(7) -0.0074(7) C11 0.0324(9) 0.0200(7) 0.0237(8) -0.0015(6) 0.0099(6) -0.0019(6) C12 0.0266(8) 0.0220(7) 0.0203(7) 0.0000(6) 0.0096(6) -0.0006(6) C13 0.0271(8) 0.0161(7) 0.0191(7) 0.0018(6) 0.0107(6) 0.0027(6) C14 0.0236(8) 0.0191(7) 0.0206(7) -0.0003(6) 0.0081(6) -0.0003(6) C15 0.0260(8) 0.0190(7) 0.0175(7) -0.0001(6) 0.0080(6) 0.0013(6) C16 0.0257(8) 0.0166(7) 0.0224(7) 0.0028(6) 0.0097(6) 0.0036(6) C17 0.0226(7) 0.0178(7) 0.0241(7) 0.0012(6) 0.0067(6) -0.0003(6) C18 0.0261(8) 0.0189(7) 0.0178(7) -0.0006(6) 0.0063(6) 0.0010(6) C19 0.0231(8) 0.0221(7) 0.0245(7) 0.0034(6) 0.0087(6) -0.0007(6) C20 0.0228(8) 0.0217(7) 0.0241(7) 0.0018(6) 0.0100(6) -0.0002(6) C21 0.0205(7) 0.0217(7) 0.0222(7) 0.0013(6) 0.0080(6) 0.0018(6) C22 0.0239(8) 0.0184(7) 0.0279(8) 0.0017(6) 0.0115(6) -0.0003(6) C23 0.0243(8) 0.0187(7) 0.0243(7) -0.0003(6) 0.0097(6) 0.0023(6) C24 0.0198(7) 0.0206(7) 0.0237(7) 0.0017(6) 0.0097(6) 0.0021(6) C25 0.0258(8) 0.0204(7) 0.0278(8) 0.0003(6) 0.0121(6) -0.0035(6) C26 0.0279(8) 0.0209(7) 0.0243(7) -0.0034(6) 0.0109(6) -0.0032(6) C27 0.0215(7) 0.0202(7) 0.0243(7) 0.0007(6) 0.0089(6) 0.0000(6) N1 0.0329(7) 0.0186(6) 0.0206(6) -0.0031(5) 0.0141(5) -0.0028(5) O1 0.0380(7) 0.0234(6) 0.0288(6) -0.0024(5) 0.0178(5) -0.0002(5) O2 0.0415(7) 0.0243(6) 0.0325(6) 0.0017(5) 0.0227(5) -0.0029(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.387(2) . ? C1 C2 1.392(2) . ? C1 N1 1.4351(18) . ? C2 C3 1.382(2) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.383(2) . ? C4 H4 0.9500 . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.396(2) . ? C7 C8 1.404(2) . ? C7 N1 1.4153(19) . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 C10 1.381(2) . ? C9 H9 0.9500 . ? C10 C11 1.388(2) . ? C10 H10 0.9500 . ? C11 C12 1.390(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.400(2) . ? C13 C18 1.401(2) . ? C13 N1 1.4156(18) . ? C14 C15 1.380(2) . ? C14 H14 0.9500 . ? C15 C16 1.399(2) . ? C15 H15 0.9500 . ? C16 C17 1.394(2) . ? C16 C19 1.470(2) . ? C17 C18 1.390(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.338(2) . ? C19 H19 0.9500 . ? C20 C21 1.466(2) . ? C20 H20 0.9500 . ? C21 C22 1.399(2) . ? C21 C26 1.403(2) . ? C22 C23 1.381(2) . ? C22 H22 0.9500 . ? C23 C24 1.392(2) . ? C23 H23 0.9500 . ? C24 C25 1.395(2) . ? C24 C27 1.477(2) . ? C25 C26 1.385(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O1 1.2492(18) . ? C27 O2 1.2976(18) . ? O2 H2A 0.8400 . ? 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 C6 C1 C2 119.95(13) . . ? C6 C1 N1 120.31(13) . . ? C2 C1 N1 119.73(13) . . ? C3 C2 C1 119.69(14) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.41(15) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.75(14) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.32(14) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 119.87(14) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 C7 C8 118.51(14) . . ? C12 C7 N1 121.67(13) . . ? C8 C7 N1 119.79(13) . . ? C9 C8 C7 120.19(14) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 121.04(14) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 119.13(14) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C12 120.59(14) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 120.51(14) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C14 C13 C18 118.35(13) . . ? C14 C13 N1 121.22(13) . . ? C18 C13 N1 120.41(13) . . ? C15 C14 C13 120.45(14) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 121.92(13) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C17 C16 C15 117.13(13) . . ? C17 C16 C19 122.08(14) . . ? C15 C16 C19 120.77(13) . . ? C18 C17 C16 121.81(14) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C13 120.19(13) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? C20 C19 C16 122.73(14) . . ? C20 C19 H19 118.6 . . ? C16 C19 H19 118.6 . . ? C19 C20 C21 128.66(14) . . ? C19 C20 H20 115.7 . . ? C21 C20 H20 115.7 . . ? C22 C21 C26 118.31(13) . . ? C22 C21 C20 118.10(13) . . ? C26 C21 C20 123.49(13) . . ? C23 C22 C21 121.22(14) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 120.04(14) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C25 119.43(13) . . ? C23 C24 C27 119.14(13) . . ? C25 C24 C27 121.43(13) . . ? C26 C25 C24 120.42(14) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C21 120.52(14) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? O1 C27 O2 122.88(13) . . ? O1 C27 C24 120.69(13) . . ? O2 C27 C24 116.43(13) . . ? C7 N1 C13 122.80(12) . . ? C7 N1 C1 119.35(12) . . ? C13 N1 C1 117.78(12) . . ? C27 O2 H2A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(2) . . . . ? N1 C1 C2 C3 178.68(14) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? N1 C1 C6 C5 -179.27(14) . . . . ? C12 C7 C8 C9 -0.7(2) . . . . ? N1 C7 C8 C9 177.59(14) . . . . ? C7 C8 C9 C10 1.4(2) . . . . ? C8 C9 C10 C11 -0.6(2) . . . . ? C9 C10 C11 C12 -0.9(2) . . . . ? C10 C11 C12 C7 1.5(2) . . . . ? C8 C7 C12 C11 -0.7(2) . . . . ? N1 C7 C12 C11 -179.00(13) . . . . ? C18 C13 C14 C15 -3.7(2) . . . . ? N1 C13 C14 C15 177.89(13) . . . . ? C13 C14 C15 C16 1.6(2) . . . . ? C14 C15 C16 C17 2.0(2) . . . . ? C14 C15 C16 C19 -179.59(13) . . . . ? C15 C16 C17 C18 -3.6(2) . . . . ? C19 C16 C17 C18 178.09(14) . . . . ? C16 C17 C18 C13 1.5(2) . . . . ? C14 C13 C18 C17 2.2(2) . . . . ? N1 C13 C18 C17 -179.37(13) . . . . ? C17 C16 C19 C20 -152.07(15) . . . . ? C15 C16 C19 C20 29.6(2) . . . . ? C16 C19 C20 C21 -173.50(14) . . . . ? C19 C20 C21 C22 -173.39(15) . . . . ? C19 C20 C21 C26 10.3(3) . . . . ? C26 C21 C22 C23 1.3(2) . . . . ? C20 C21 C22 C23 -175.26(14) . . . . ? C21 C22 C23 C24 0.9(2) . . . . ? C22 C23 C24 C25 -2.3(2) . . . . ? C22 C23 C24 C27 178.00(14) . . . . ? C23 C24 C25 C26 1.4(2) . . . . ? C27 C24 C25 C26 -178.85(14) . . . . ? C24 C25 C26 C21 0.8(2) . . . . ? C22 C21 C26 C25 -2.1(2) . . . . ? C20 C21 C26 C25 174.21(14) . . . . ? C23 C24 C27 O1 11.0(2) . . . . ? C25 C24 C27 O1 -168.70(14) . . . . ? C23 C24 C27 O2 -169.27(14) . . . . ? C25 C24 C27 O2 11.0(2) . . . . ? C12 C7 N1 C13 -24.2(2) . . . . ? C8 C7 N1 C13 157.51(14) . . . . ? C12 C7 N1 C1 152.89(14) . . . . ? C8 C7 N1 C1 -25.4(2) . . . . ? C14 C13 N1 C7 -34.5(2) . . . . ? C18 C13 N1 C7 147.16(14) . . . . ? C14 C13 N1 C1 148.36(14) . . . . ? C18 C13 N1 C1 -30.0(2) . . . . ? C6 C1 N1 C7 -58.7(2) . . . . ? C2 C1 N1 C7 122.29(16) . . . . ? C6 C1 N1 C13 118.57(15) . . . . ? C2 C1 N1 C13 -60.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A O1 0.84 1.80 2.6346(15) 174.5 3_557 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.213 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.051 #===END # Attachment '- Holliman_dyes_combined.cif' #TrackingRef '- Holliman_dyes_combined.cif' data_ssj0089_compound_2 _database_code_depnum_ccdc_archive 'CCDC 838488' #TrackingRef '- Holliman_dyes_combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 N' _chemical_formula_sum 'C20 H17 N' _chemical_formula_weight 271.35 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.000(2) _cell_length_b 18.679(4) _cell_length_c 15.789(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.675(2) _cell_angle_gamma 90.00 _cell_volume 2948.0(11) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9909 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _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 120(2) _diffrn_radiation_wavelength 0.6889 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Diamond beamline I19' _diffrn_radiation_monochromator 'silicon double crystal' _diffrn_measurement_device_type 'Crystal Logic diffractometer and Rigaku Saturn 724+ detector' _diffrn_measurement_method 'thick-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25445 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5998 _reflns_number_gt 4684 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Rigaku CrystalClear' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0613P)^2^+2.5596P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5998 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1633 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.46372(19) 0.23310(10) 0.75452(11) 0.0311(4) Uani 1 1 d . . . C1 C 0.4250(2) 0.16887(11) 0.79627(13) 0.0292(5) Uani 1 1 d . . . C2 C 0.2979(2) 0.16141(12) 0.82842(14) 0.0304(5) Uani 1 1 d . . . H2 H 0.2370 0.2004 0.8257 0.036 Uiso 1 1 calc R . . C3 C 0.2597(2) 0.09728(13) 0.86438(14) 0.0335(5) Uani 1 1 d . . . H3 H 0.1732 0.0928 0.8872 0.040 Uiso 1 1 calc R . . C4 C 0.3473(2) 0.03942(13) 0.86733(14) 0.0353(5) Uani 1 1 d . . . H4 H 0.3199 -0.0051 0.8902 0.042 Uiso 1 1 calc R . . C5 C 0.4745(2) 0.04733(13) 0.83675(14) 0.0351(5) Uani 1 1 d . . . H5 H 0.5355 0.0084 0.8401 0.042 Uiso 1 1 calc R . . C6 C 0.5140(2) 0.11152(12) 0.80130(14) 0.0319(5) Uani 1 1 d . . . H6 H 0.6017 0.1164 0.7804 0.038 Uiso 1 1 calc R . . C7 C 0.5199(2) 0.22639(12) 0.67302(13) 0.0284(5) Uani 1 1 d . . . C8 C 0.4765(2) 0.17110(12) 0.61971(14) 0.0309(5) Uani 1 1 d . . . H8 H 0.4071 0.1401 0.6370 0.037 Uiso 1 1 calc R . . C9 C 0.5335(2) 0.16104(13) 0.54177(14) 0.0334(5) Uani 1 1 d . . . H9 H 0.5039 0.1227 0.5064 0.040 Uiso 1 1 calc R . . C10 C 0.6332(2) 0.20615(13) 0.51493(14) 0.0328(5) Uani 1 1 d . . . H10 H 0.6723 0.1991 0.4615 0.039 Uiso 1 1 calc R . . C11 C 0.6752(2) 0.26197(13) 0.56734(14) 0.0331(5) Uani 1 1 d . . . H11 H 0.7427 0.2937 0.5490 0.040 Uiso 1 1 calc R . . C12 C 0.6203(2) 0.27211(12) 0.64590(14) 0.0319(5) Uani 1 1 d . . . H12 H 0.6509 0.3102 0.6813 0.038 Uiso 1 1 calc R . . C13 C 0.4408(2) 0.30001(12) 0.79294(14) 0.0287(5) Uani 1 1 d . . . C14 C 0.4112(2) 0.36139(12) 0.74545(14) 0.0313(5) Uani 1 1 d . . . H14 H 0.4068 0.3587 0.6853 0.038 Uiso 1 1 calc R . . C15 C 0.3883(2) 0.42594(12) 0.78514(14) 0.0316(5) Uani 1 1 d . . . H15 H 0.3701 0.4673 0.7516 0.038 Uiso 1 1 calc R . . C16 C 0.3912(2) 0.43195(12) 0.87369(14) 0.0287(5) Uani 1 1 d . . . C17 C 0.4202(2) 0.37036(12) 0.92017(14) 0.0299(5) Uani 1 1 d . . . H17 H 0.4227 0.3729 0.9803 0.036 Uiso 1 1 calc R . . C18 C 0.4454(2) 0.30542(12) 0.88151(14) 0.0296(5) Uani 1 1 d . . . H18 H 0.4658 0.2644 0.9151 0.036 Uiso 1 1 calc R . . C19 C 0.3656(2) 0.49929(12) 0.91854(15) 0.0324(5) Uani 1 1 d . . . H19 H 0.3697 0.4972 0.9787 0.039 Uiso 1 1 calc R . . C20 C 0.3375(2) 0.56278(13) 0.88451(16) 0.0377(6) Uani 1 1 d . . . H20A H 0.3322 0.5681 0.8247 0.045 Uiso 1 1 calc R . . H20B H 0.3227 0.6029 0.9200 0.045 Uiso 1 1 calc R . . N101 N 0.46556(19) 0.21593(10) 0.25359(12) 0.0316(4) Uani 1 1 d . . . C101 C 0.5199(2) 0.20122(12) 0.17303(13) 0.0286(5) Uani 1 1 d . . . C102 C 0.6265(2) 0.24071(13) 0.14283(14) 0.0333(5) Uani 1 1 d . . . H102 H 0.6640 0.2785 0.1760 0.040 Uiso 1 1 calc R . . C103 C 0.6780(2) 0.22497(13) 0.06423(14) 0.0360(5) Uani 1 1 d . . . H103 H 0.7496 0.2527 0.0434 0.043 Uiso 1 1 calc R . . C104 C 0.6256(2) 0.16920(13) 0.01597(14) 0.0351(5) Uani 1 1 d . . . H104 H 0.6613 0.1584 -0.0376 0.042 Uiso 1 1 calc R . . C105 C 0.5208(2) 0.12936(13) 0.04633(14) 0.0339(5) Uani 1 1 d . . . H105 H 0.4849 0.0908 0.0137 0.041 Uiso 1 1 calc R . . C106 C 0.4679(2) 0.14545(12) 0.12440(14) 0.0308(5) Uani 1 1 d . . . H106 H 0.3954 0.1180 0.1446 0.037 Uiso 1 1 calc R . . C107 C 0.4307(2) 0.15592(12) 0.30463(13) 0.0292(5) Uani 1 1 d . . . C108 C 0.5217(2) 0.10021(12) 0.31530(14) 0.0316(5) Uani 1 1 d . . . H108 H 0.6081 0.1038 0.2922 0.038 Uiso 1 1 calc R . . C109 C 0.4865(2) 0.03933(12) 0.35962(14) 0.0329(5) Uani 1 1 d . . . H109 H 0.5487 0.0011 0.3663 0.040 Uiso 1 1 calc R . . C110 C 0.3618(2) 0.03395(12) 0.39409(14) 0.0343(5) Uani 1 1 d . . . H110 H 0.3376 -0.0081 0.4239 0.041 Uiso 1 1 calc R . . C111 C 0.2720(2) 0.09001(13) 0.38513(14) 0.0338(5) Uani 1 1 d . . . H111 H 0.1867 0.0867 0.4098 0.041 Uiso 1 1 calc R . . C112 C 0.3057(2) 0.15098(12) 0.34049(14) 0.0312(5) Uani 1 1 d . . . H112 H 0.2436 0.1893 0.3344 0.037 Uiso 1 1 calc R . . C113 C 0.4337(2) 0.28650(12) 0.27790(14) 0.0283(5) Uani 1 1 d . . . C114 C 0.4323(2) 0.30508(12) 0.36364(14) 0.0299(5) Uani 1 1 d . . . H114 H 0.4501 0.2695 0.4055 0.036 Uiso 1 1 calc R . . C115 C 0.4055(2) 0.37433(12) 0.38841(14) 0.0303(5) Uani 1 1 d . . . H115 H 0.4051 0.3855 0.4471 0.036 Uiso 1 1 calc R . . C116 C 0.3789(2) 0.42854(12) 0.32893(14) 0.0301(5) Uani 1 1 d . . . C117 C 0.3794(2) 0.40919(12) 0.24361(14) 0.0318(5) Uani 1 1 d . . . H117 H 0.3620 0.4448 0.2018 0.038 Uiso 1 1 calc R . . C118 C 0.4046(2) 0.33958(12) 0.21793(14) 0.0315(5) Uani 1 1 d . . . H118 H 0.4020 0.3280 0.1593 0.038 Uiso 1 1 calc R . . C119 C 0.3532(2) 0.50290(13) 0.35336(16) 0.0355(5) Uani 1 1 d . . . H119 H 0.3383 0.5360 0.3084 0.043 Uiso 1 1 calc R . . C120 C 0.3485(3) 0.52885(15) 0.43082(18) 0.0495(7) Uani 1 1 d . . . H12A H 0.3626 0.4981 0.4782 0.059 Uiso 1 1 calc R . . H12B H 0.3309 0.5783 0.4393 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0383(10) 0.0247(10) 0.0306(9) -0.0010(7) 0.0083(8) 0.0002(8) C1 0.0336(11) 0.0257(11) 0.0283(10) -0.0029(9) 0.0023(9) -0.0012(9) C2 0.0292(11) 0.0298(12) 0.0323(11) -0.0007(9) 0.0010(9) 0.0033(9) C3 0.0313(11) 0.0373(13) 0.0319(11) 0.0027(10) 0.0002(9) -0.0042(10) C4 0.0443(13) 0.0287(12) 0.0326(11) 0.0012(9) -0.0002(10) -0.0049(10) C5 0.0434(13) 0.0292(12) 0.0327(11) -0.0010(9) 0.0006(10) 0.0064(10) C6 0.0334(12) 0.0321(12) 0.0302(11) -0.0020(9) 0.0042(9) 0.0022(9) C7 0.0282(11) 0.0284(11) 0.0288(11) 0.0001(9) 0.0037(8) 0.0034(9) C8 0.0279(11) 0.0302(12) 0.0347(11) -0.0004(9) 0.0012(9) -0.0004(9) C9 0.0390(12) 0.0306(12) 0.0303(11) -0.0047(9) -0.0024(9) 0.0030(10) C10 0.0341(12) 0.0366(13) 0.0280(11) 0.0004(9) 0.0037(9) 0.0072(10) C11 0.0289(11) 0.0362(13) 0.0344(12) 0.0025(10) 0.0042(9) -0.0017(9) C12 0.0312(11) 0.0318(12) 0.0327(11) -0.0036(9) 0.0010(9) -0.0018(9) C13 0.0265(10) 0.0266(11) 0.0332(11) -0.0028(9) 0.0055(8) -0.0016(8) C14 0.0322(11) 0.0319(12) 0.0302(11) -0.0005(9) 0.0041(9) -0.0005(9) C15 0.0299(11) 0.0288(12) 0.0363(12) 0.0025(9) 0.0030(9) 0.0011(9) C16 0.0245(10) 0.0261(11) 0.0356(11) -0.0024(9) 0.0033(8) -0.0008(8) C17 0.0293(11) 0.0309(12) 0.0297(11) -0.0019(9) 0.0029(9) -0.0020(9) C18 0.0336(11) 0.0242(11) 0.0311(11) 0.0011(9) 0.0021(9) -0.0017(9) C19 0.0309(11) 0.0314(12) 0.0351(12) -0.0040(9) 0.0034(9) 0.0010(9) C20 0.0387(13) 0.0310(13) 0.0435(13) -0.0047(10) 0.0047(10) 0.0022(10) N101 0.0399(11) 0.0244(10) 0.0311(9) 0.0003(7) 0.0093(8) 0.0005(8) C101 0.0307(11) 0.0273(11) 0.0278(10) 0.0005(8) 0.0026(8) 0.0049(9) C102 0.0345(12) 0.0338(13) 0.0316(11) -0.0023(9) 0.0020(9) -0.0026(10) C103 0.0332(12) 0.0422(14) 0.0329(12) 0.0020(10) 0.0043(9) -0.0011(10) C104 0.0364(12) 0.0402(14) 0.0289(11) -0.0004(10) 0.0043(9) 0.0092(10) C105 0.0362(12) 0.0329(12) 0.0322(11) -0.0047(9) -0.0033(9) 0.0055(10) C106 0.0306(11) 0.0278(12) 0.0340(11) 0.0008(9) 0.0008(9) 0.0029(9) C107 0.0334(11) 0.0268(11) 0.0276(10) -0.0015(9) 0.0024(8) -0.0013(9) C108 0.0306(11) 0.0328(12) 0.0315(11) -0.0015(9) 0.0042(9) 0.0026(9) C109 0.0415(13) 0.0257(12) 0.0315(11) -0.0002(9) -0.0001(9) 0.0065(9) C110 0.0423(13) 0.0252(12) 0.0354(12) 0.0026(9) -0.0002(10) -0.0044(10) C111 0.0312(12) 0.0347(13) 0.0356(12) 0.0006(10) 0.0035(9) -0.0048(9) C112 0.0300(11) 0.0309(12) 0.0327(11) 0.0016(9) 0.0004(9) 0.0015(9) C113 0.0271(10) 0.0260(11) 0.0322(11) -0.0016(9) 0.0056(8) -0.0013(8) C114 0.0293(11) 0.0301(12) 0.0305(11) 0.0016(9) 0.0030(9) 0.0002(9) C115 0.0285(11) 0.0311(12) 0.0315(11) -0.0036(9) 0.0049(9) -0.0014(9) C116 0.0244(10) 0.0288(12) 0.0373(12) -0.0013(9) 0.0042(9) -0.0012(9) C117 0.0309(11) 0.0292(12) 0.0355(12) 0.0054(9) 0.0039(9) 0.0009(9) C118 0.0340(11) 0.0316(12) 0.0288(11) -0.0004(9) 0.0027(9) -0.0007(9) C119 0.0339(12) 0.0297(12) 0.0431(13) 0.0011(10) 0.0060(10) 0.0033(9) C120 0.0647(18) 0.0333(14) 0.0505(15) -0.0073(12) 0.0025(13) 0.0114(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 N1 C1 1.428(3) . ? N1 C7 1.424(3) . ? N1 C13 1.411(3) . ? C1 C2 1.389(3) . ? C1 C6 1.394(3) . ? C2 H2 0.950 . ? C2 C3 1.384(3) . ? C3 H3 0.950 . ? C3 C4 1.391(3) . ? C4 H4 0.950 . ? C4 C5 1.382(3) . ? C5 H5 0.950 . ? C5 C6 1.385(3) . ? C6 H6 0.950 . ? C7 C8 1.394(3) . ? C7 C12 1.395(3) . ? C8 H8 0.950 . ? C8 C9 1.384(3) . ? C9 H9 0.950 . ? C9 C10 1.381(3) . ? C10 H10 0.950 . ? C10 C11 1.389(3) . ? C11 H11 0.950 . ? C11 C12 1.384(3) . ? C12 H12 0.950 . ? C13 C14 1.397(3) . ? C13 C18 1.402(3) . ? C14 H14 0.950 . ? C14 C15 1.381(3) . ? C15 H15 0.950 . ? C15 C16 1.402(3) . ? C16 C17 1.390(3) . ? C16 C19 1.470(3) . ? C17 H17 0.950 . ? C17 C18 1.384(3) . ? C18 H18 0.950 . ? C19 H19 0.950 . ? C19 C20 1.329(3) . ? C20 H20A 0.950 . ? C20 H20B 0.950 . ? N101 C101 1.424(3) . ? N101 C107 1.430(3) . ? N101 C113 1.412(3) . ? C101 C102 1.392(3) . ? C101 C106 1.386(3) . ? C102 H102 0.950 . ? C102 C103 1.389(3) . ? C103 H103 0.950 . ? C103 C104 1.385(3) . ? C104 H104 0.950 . ? C104 C105 1.382(3) . ? C105 H105 0.950 . ? C105 C106 1.389(3) . ? C106 H106 0.950 . ? C107 C108 1.389(3) . ? C107 C112 1.391(3) . ? C108 H108 0.950 . ? C108 C109 1.386(3) . ? C109 H109 0.950 . ? C109 C110 1.379(3) . ? C110 H110 0.950 . ? C110 C111 1.384(3) . ? C111 H111 0.950 . ? C111 C112 1.386(3) . ? C112 H112 0.950 . ? C113 C114 1.398(3) . ? C113 C118 1.396(3) . ? C114 H114 0.950 . ? C114 C115 1.380(3) . ? C115 H115 0.950 . ? C115 C116 1.401(3) . ? C116 C117 1.395(3) . ? C116 C119 1.466(3) . ? C117 H117 0.950 . ? C117 C118 1.387(3) . ? C118 H118 0.950 . ? C119 H119 0.950 . ? C119 C120 1.318(4) . ? C120 H12A 0.950 . ? C120 H12B 0.950 . ? 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 C1 N1 C7 117.55(17) . . ? C1 N1 C13 119.73(17) . . ? C7 N1 C13 122.67(18) . . ? N1 C1 C2 121.1(2) . . ? N1 C1 C6 119.4(2) . . ? C2 C1 C6 119.4(2) . . ? C1 C2 H2 119.9 . . ? C1 C2 C3 120.2(2) . . ? H2 C2 C3 119.9 . . ? C2 C3 H3 119.8 . . ? C2 C3 C4 120.3(2) . . ? H3 C3 C4 119.8 . . ? C3 C4 H4 120.3 . . ? C3 C4 C5 119.4(2) . . ? H4 C4 C5 120.3 . . ? C4 C5 H5 119.7 . . ? C4 C5 C6 120.6(2) . . ? H5 C5 C6 119.7 . . ? C1 C6 C5 119.9(2) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? N1 C7 C8 119.13(19) . . ? N1 C7 C12 122.0(2) . . ? C8 C7 C12 118.9(2) . . ? C7 C8 H8 119.7 . . ? C7 C8 C9 120.5(2) . . ? H8 C8 C9 119.7 . . ? C8 C9 H9 119.7 . . ? C8 C9 C10 120.6(2) . . ? H9 C9 C10 119.7 . . ? C9 C10 H10 120.5 . . ? C9 C10 C11 118.9(2) . . ? H10 C10 C11 120.5 . . ? C10 C11 H11 119.5 . . ? C10 C11 C12 121.0(2) . . ? H11 C11 C12 119.5 . . ? C7 C12 C11 120.0(2) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? N1 C13 C14 122.06(19) . . ? N1 C13 C18 119.47(19) . . ? C14 C13 C18 118.5(2) . . ? C13 C14 H14 119.7 . . ? C13 C14 C15 120.6(2) . . ? H14 C14 C15 119.7 . . ? C14 C15 H15 119.2 . . ? C14 C15 C16 121.6(2) . . ? H15 C15 C16 119.2 . . ? C15 C16 C17 117.3(2) . . ? C15 C16 C19 123.4(2) . . ? C17 C16 C19 119.3(2) . . ? C16 C17 H17 119.0 . . ? C16 C17 C18 122.0(2) . . ? H17 C17 C18 119.0 . . ? C13 C18 C17 120.1(2) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C16 C19 H19 116.3 . . ? C16 C19 C20 127.4(2) . . ? H19 C19 C20 116.3 . . ? C19 C20 H20A 120.0 . . ? C19 C20 H20B 120.0 . . ? H20A C20 H20B 120.0 . . ? C101 N101 C107 117.24(18) . . ? C101 N101 C113 121.19(18) . . ? C107 N101 C113 121.21(17) . . ? N101 C101 C102 121.3(2) . . ? N101 C101 C106 119.5(2) . . ? C102 C101 C106 119.2(2) . . ? C101 C102 H102 119.9 . . ? C101 C102 C103 120.1(2) . . ? H102 C102 C103 119.9 . . ? C102 C103 H103 119.8 . . ? C102 C103 C104 120.4(2) . . ? H103 C103 C104 119.8 . . ? C103 C104 H104 120.2 . . ? C103 C104 C105 119.5(2) . . ? H104 C104 C105 120.2 . . ? C104 C105 H105 119.9 . . ? C104 C105 C106 120.3(2) . . ? H105 C105 C106 119.9 . . ? C101 C106 C105 120.5(2) . . ? C101 C106 H106 119.8 . . ? C105 C106 H106 119.8 . . ? N101 C107 C108 119.1(2) . . ? N101 C107 C112 121.2(2) . . ? C108 C107 C112 119.6(2) . . ? C107 C108 H108 120.0 . . ? C107 C108 C109 120.1(2) . . ? H108 C108 C109 120.0 . . ? C108 C109 H109 119.8 . . ? C108 C109 C110 120.3(2) . . ? H109 C109 C110 119.8 . . ? C109 C110 H110 120.1 . . ? C109 C110 C111 119.7(2) . . ? H110 C110 C111 120.1 . . ? C110 C111 H111 119.8 . . ? C110 C111 C112 120.5(2) . . ? H111 C111 C112 119.8 . . ? C107 C112 C111 119.7(2) . . ? C107 C112 H112 120.1 . . ? C111 C112 H112 120.1 . . ? N101 C113 C114 120.2(2) . . ? N101 C113 C118 121.54(19) . . ? C114 C113 C118 118.2(2) . . ? C113 C114 H114 119.5 . . ? C113 C114 C115 121.0(2) . . ? H114 C114 C115 119.5 . . ? C114 C115 H115 119.3 . . ? C114 C115 C116 121.5(2) . . ? H115 C115 C116 119.3 . . ? C115 C116 C117 117.0(2) . . ? C115 C116 C119 122.6(2) . . ? C117 C116 C119 120.4(2) . . ? C116 C117 H117 119.0 . . ? C116 C117 C118 122.1(2) . . ? H117 C117 C118 119.0 . . ? C113 C118 C117 120.2(2) . . ? C113 C118 H118 119.9 . . ? C117 C118 H118 119.9 . . ? C116 C119 H119 116.4 . . ? C116 C119 C120 127.2(2) . . ? H119 C119 C120 116.4 . . ? C119 C120 H12A 120.0 . . ? C119 C120 H12B 120.0 . . ? H12A C120 H12B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C1 C2 -128.4(2) . . . . ? C7 N1 C1 C6 48.6(3) . . . . ? C13 N1 C1 C2 49.1(3) . . . . ? C13 N1 C1 C6 -133.9(2) . . . . ? N1 C1 C2 C3 176.3(2) . . . . ? C6 C1 C2 C3 -0.6(3) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C2 C3 C4 C5 2.3(3) . . . . ? C3 C4 C5 C6 -1.7(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? N1 C1 C6 C5 -175.8(2) . . . . ? C2 C1 C6 C5 1.2(3) . . . . ? C1 N1 C7 C8 32.5(3) . . . . ? C1 N1 C7 C12 -145.3(2) . . . . ? C13 N1 C7 C8 -144.9(2) . . . . ? C13 N1 C7 C12 37.2(3) . . . . ? N1 C7 C8 C9 -176.9(2) . . . . ? C12 C7 C8 C9 1.0(3) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C12 1.0(3) . . . . ? C10 C11 C12 C7 -0.8(3) . . . . ? N1 C7 C12 C11 177.7(2) . . . . ? C8 C7 C12 C11 -0.2(3) . . . . ? C1 N1 C13 C14 -147.1(2) . . . . ? C1 N1 C13 C18 31.8(3) . . . . ? C7 N1 C13 C14 30.2(3) . . . . ? C7 N1 C13 C18 -150.8(2) . . . . ? N1 C13 C14 C15 179.5(2) . . . . ? C18 C13 C14 C15 0.6(3) . . . . ? C13 C14 C15 C16 -1.3(3) . . . . ? C14 C15 C16 C17 0.9(3) . . . . ? C14 C15 C16 C19 -179.1(2) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? C19 C16 C17 C18 -179.9(2) . . . . ? C16 C17 C18 C13 -0.7(3) . . . . ? N1 C13 C18 C17 -178.58(19) . . . . ? C14 C13 C18 C17 0.4(3) . . . . ? C15 C16 C19 C20 -0.4(4) . . . . ? C17 C16 C19 C20 179.6(2) . . . . ? C107 N101 C101 C102 -138.9(2) . . . . ? C107 N101 C101 C106 39.6(3) . . . . ? C113 N101 C101 C102 48.0(3) . . . . ? C113 N101 C101 C106 -133.5(2) . . . . ? N101 C101 C102 C103 179.6(2) . . . . ? C106 C101 C102 C103 1.2(3) . . . . ? C101 C102 C103 C104 -1.2(4) . . . . ? C102 C103 C104 C105 0.3(4) . . . . ? C103 C104 C105 C106 0.5(3) . . . . ? N101 C101 C106 C105 -178.9(2) . . . . ? C102 C101 C106 C105 -0.3(3) . . . . ? C104 C105 C106 C101 -0.5(3) . . . . ? C101 N101 C107 C108 47.6(3) . . . . ? C101 N101 C107 C112 -129.6(2) . . . . ? C113 N101 C107 C108 -139.3(2) . . . . ? C113 N101 C107 C112 43.6(3) . . . . ? N101 C107 C108 C109 -175.5(2) . . . . ? C112 C107 C108 C109 1.6(3) . . . . ? C107 C108 C109 C110 -0.7(3) . . . . ? C108 C109 C110 C111 -0.7(3) . . . . ? C109 C110 C111 C112 1.2(3) . . . . ? C110 C111 C112 C107 -0.2(3) . . . . ? N101 C107 C112 C111 175.9(2) . . . . ? C108 C107 C112 C111 -1.2(3) . . . . ? C101 N101 C113 C114 -154.4(2) . . . . ? C101 N101 C113 C118 24.7(3) . . . . ? C107 N101 C113 C114 32.7(3) . . . . ? C107 N101 C113 C118 -148.1(2) . . . . ? N101 C113 C114 C115 177.95(19) . . . . ? C118 C113 C114 C115 -1.2(3) . . . . ? C113 C114 C115 C116 -0.1(3) . . . . ? C114 C115 C116 C117 0.6(3) . . . . ? C114 C115 C116 C119 -178.5(2) . . . . ? C115 C116 C117 C118 0.2(3) . . . . ? C119 C116 C117 C118 179.4(2) . . . . ? C116 C117 C118 C113 -1.6(3) . . . . ? N101 C113 C118 C117 -177.1(2) . . . . ? C114 C113 C118 C117 2.0(3) . . . . ? C115 C116 C119 C120 -1.5(4) . . . . ? C117 C116 C119 C120 179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.259 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.055