# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Xufeng Lin' _publ_contact_author_email lxfok@zju.edu.cn loop_ _publ_author_name 'Xufeng Lin' 'Zhenjun Mao' 'Xixiang Dai' 'Ping Lu' 'Yanguang Wang' data_SHX97 _database_code_depnum_ccdc_archive 'CCDC 798900' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C27 H23 N O4' _chemical_formula_sum 'C27 H23 N O4' _chemical_formula_weight 425.46 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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 Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.8980(9) _cell_length_b 8.2290(4) _cell_length_c 15.4709(6) _cell_measurement_reflns_used 2902 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 67.6387 _cell_measurement_theta_min 2.8569 _cell_volume 2278.59(18) _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_crystal_F_000 896 _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.3592 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 5697 _diffrn_reflns_theta_full 25.26 _diffrn_reflns_theta_max 25.26 _diffrn_reflns_theta_min 2.28 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2601 _reflns_number_total 3307 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)/Bruker' _refine_diff_density_max 0.227 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.055 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0544 _refine_ls_abs_structure_Flack 4.1(18) _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 3307 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1461 _refine_ls_wR_factor_ref 0.1597 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.1104P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.7724(3) 0.3250(9) 0.5865(4) 0.0989(17) Uani 1 1 d . . . H1A H 0.8011 0.2441 0.5566 0.148 Uiso 1 1 calc R . . H1B H 0.7916 0.3380 0.6441 0.148 Uiso 1 1 calc R . . H1C H 0.7758 0.4265 0.5562 0.148 Uiso 1 1 calc R . . C2 C 0.6939(3) 0.2737(6) 0.5907(3) 0.0829(13) Uani 1 1 d . . . H2A H 0.6742 0.2592 0.5328 0.099 Uiso 1 1 calc R . . H2B H 0.6899 0.1711 0.6212 0.099 Uiso 1 1 calc R . . C3 C 0.5781(2) 0.3884(4) 0.63539(19) 0.0564(8) Uani 1 1 d . . . C4 C 0.5406(2) 0.5201(4) 0.6848(2) 0.0514(7) Uani 1 1 d . . . C5 C 0.57117(18) 0.6568(4) 0.7241(2) 0.0492(7) Uani 1 1 d . . . C6 C 0.64924(19) 0.7164(4) 0.7311(2) 0.0506(7) Uani 1 1 d . . . C7 C 0.6938(2) 0.7531(4) 0.6533(2) 0.0550(8) Uani 1 1 d . . . C8 C 0.7706(2) 0.7702(5) 0.6595(3) 0.0679(10) Uani 1 1 d . . . H8A H 0.7938 0.7568 0.7128 0.081 Uiso 1 1 calc R . . C9 C 0.8133(3) 0.8068(7) 0.5877(3) 0.0850(14) Uani 1 1 d . . . H9A H 0.8649 0.8157 0.5922 0.102 Uiso 1 1 calc R . . C10 C 0.7786(3) 0.8301(8) 0.5093(3) 0.0902(15) Uani 1 1 d . . . H10A H 0.8068 0.8568 0.4609 0.108 Uiso 1 1 calc R . . C11 C 0.7025(4) 0.8142(8) 0.5022(3) 0.0933(16) Uani 1 1 d . . . H11A H 0.6798 0.8294 0.4488 0.112 Uiso 1 1 calc R . . C12 C 0.6591(3) 0.7759(5) 0.5734(3) 0.0691(10) Uani 1 1 d . . . H12A H 0.6076 0.7656 0.5680 0.083 Uiso 1 1 calc R . . C13 C 0.52055(16) 0.8740(4) 0.8212(2) 0.0468(7) Uani 1 1 d . . . C14 C 0.5339(2) 1.0252(4) 0.7855(2) 0.0555(8) Uani 1 1 d . . . H14A H 0.5412 1.0348 0.7262 0.067 Uiso 1 1 calc R . . C15 C 0.5363(2) 1.1609(4) 0.8367(2) 0.0576(8) Uani 1 1 d . . . H15A H 0.5449 1.2621 0.8119 0.069 Uiso 1 1 calc R . . C16 C 0.5258(2) 1.1481(4) 0.9259(2) 0.0544(8) Uani 1 1 d . . . C17 C 0.5113(2) 0.9972(4) 0.9602(2) 0.0596(9) Uani 1 1 d . . . H17A H 0.5031 0.9873 1.0193 0.071 Uiso 1 1 calc R . . C18 C 0.5086(2) 0.8623(4) 0.9098(2) 0.0532(8) Uani 1 1 d . . . H18A H 0.4987 0.7616 0.9346 0.064 Uiso 1 1 calc R . . C19 C 0.5407(3) 1.4320(5) 0.9494(3) 0.0790(12) Uani 1 1 d . . . H19A H 0.5417 1.5079 0.9965 0.118 Uiso 1 1 calc R . . H19B H 0.5008 1.4597 0.9107 0.118 Uiso 1 1 calc R . . H19C H 0.5874 1.4361 0.9191 0.118 Uiso 1 1 calc R . . C20 C 0.3476(2) 0.8505(5) 0.7886(3) 0.0675(9) Uani 1 1 d . . . H20A H 0.3763 0.9323 0.7637 0.081 Uiso 1 1 calc R . . C21 C 0.2779(2) 0.8855(6) 0.8202(3) 0.0793(12) Uani 1 1 d . . . H21A H 0.2597 0.9912 0.8171 0.095 Uiso 1 1 calc R . . C22 C 0.2346(3) 0.7654(7) 0.8566(4) 0.0890(14) Uani 1 1 d . . . H22A H 0.1877 0.7903 0.8788 0.107 Uiso 1 1 calc R . . C23 C 0.2608(3) 0.6080(7) 0.8600(3) 0.0842(13) Uani 1 1 d . . . H23A H 0.2309 0.5261 0.8828 0.101 Uiso 1 1 calc R . . C24 C 0.3306(2) 0.5721(5) 0.8301(3) 0.0688(10) Uani 1 1 d . . . H24A H 0.3485 0.4662 0.8340 0.083 Uiso 1 1 calc R . . C25 C 0.3756(2) 0.6929(4) 0.7937(2) 0.0591(8) Uani 1 1 d . . . C26 C 0.44813(18) 0.6453(4) 0.7565(2) 0.0539(8) Uani 1 1 d . . . C27 C 0.4644(2) 0.5151(4) 0.7056(2) 0.0574(9) Uani 1 1 d . . . H27A H 0.4306 0.4361 0.6876 0.069 Uiso 1 1 calc R . . N1 N 0.51375(15) 0.7324(3) 0.76881(18) 0.0482(6) Uani 1 1 d . . . O1 O 0.5436(2) 0.2806(4) 0.6003(2) 0.0818(9) Uani 1 1 d . . . O2 O 0.65172(16) 0.3989(3) 0.63598(18) 0.0689(7) Uani 1 1 d . . . O3 O 0.67550(15) 0.7410(3) 0.80344(17) 0.0679(7) Uani 1 1 d . . . O4 O 0.52930(19) 1.2744(3) 0.98177(18) 0.0723(8) 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 0.081(3) 0.129(4) 0.087(3) -0.024(3) -0.002(3) 0.034(3) C2 0.097(3) 0.072(3) 0.080(3) -0.021(2) 0.010(3) 0.016(2) C3 0.080(2) 0.0505(17) 0.0385(15) -0.0102(15) 0.0048(15) 0.0007(17) C4 0.064(2) 0.0478(17) 0.0426(15) -0.0040(14) 0.0008(14) 0.0011(14) C5 0.0552(18) 0.0479(16) 0.0447(15) -0.0014(14) 0.0015(13) 0.0018(13) C6 0.0586(18) 0.0482(16) 0.0451(17) -0.0037(14) -0.0026(14) 0.0032(13) C7 0.064(2) 0.0469(17) 0.0537(17) -0.0034(14) 0.0021(16) 0.0012(14) C8 0.064(2) 0.081(3) 0.058(2) -0.0001(19) 0.0104(17) 0.0048(18) C9 0.074(3) 0.095(3) 0.085(3) 0.000(3) 0.025(3) -0.003(2) C10 0.100(4) 0.099(3) 0.071(3) 0.004(3) 0.025(3) -0.008(3) C11 0.118(4) 0.110(4) 0.052(2) 0.014(2) 0.006(2) -0.020(3) C12 0.081(3) 0.074(3) 0.052(2) 0.0094(19) -0.0030(18) -0.009(2) C13 0.0471(16) 0.0457(16) 0.0476(16) -0.0026(14) 0.0021(13) 0.0025(12) C14 0.073(2) 0.0457(16) 0.0474(16) 0.0029(15) 0.0058(16) 0.0009(14) C15 0.073(2) 0.0432(17) 0.0565(19) 0.0038(16) 0.0034(16) -0.0046(14) C16 0.064(2) 0.0442(18) 0.0547(18) -0.0085(15) 0.0020(15) 0.0017(15) C17 0.081(2) 0.0502(18) 0.0476(18) 0.0002(17) 0.0052(16) 0.0050(16) C18 0.070(2) 0.0421(16) 0.0473(17) 0.0014(15) 0.0044(15) 0.0000(14) C19 0.106(3) 0.0478(19) 0.083(3) -0.017(2) -0.005(2) -0.001(2) C20 0.064(2) 0.067(2) 0.071(2) -0.001(2) -0.0027(18) -0.0013(16) C21 0.062(2) 0.095(3) 0.081(3) -0.011(3) -0.004(2) 0.012(2) C22 0.059(2) 0.118(4) 0.089(3) -0.021(3) 0.009(2) 0.000(2) C23 0.070(3) 0.099(3) 0.083(3) -0.009(3) 0.018(2) -0.021(2) C24 0.068(2) 0.071(2) 0.068(2) -0.003(2) 0.0061(18) -0.0152(18) C25 0.0562(18) 0.0650(19) 0.0560(18) -0.0078(18) -0.0037(16) -0.0056(16) C26 0.0503(17) 0.0551(18) 0.0563(18) -0.0002(16) -0.0028(14) -0.0043(13) C27 0.063(2) 0.0513(18) 0.0581(19) -0.0059(17) -0.0020(15) -0.0055(15) N1 0.0540(15) 0.0444(13) 0.0462(14) -0.0043(12) 0.0021(11) -0.0008(10) O1 0.095(2) 0.0719(19) 0.0788(19) -0.0321(16) 0.0014(17) -0.0100(15) O2 0.0708(18) 0.0622(14) 0.0737(17) -0.0194(13) 0.0067(13) 0.0067(12) O3 0.0622(15) 0.0939(19) 0.0475(13) -0.0070(14) -0.0046(11) -0.0052(12) O4 0.108(2) 0.0460(14) 0.0628(16) -0.0117(13) 0.0008(15) 0.0007(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.468(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O2 1.457(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O1 1.210(4) . ? C3 O2 1.320(5) . ? C3 C4 1.486(5) . ? C4 C5 1.390(5) . ? C4 C27 1.403(5) . ? C5 N1 1.386(4) . ? C5 C6 1.485(5) . ? C6 O3 1.231(4) . ? C6 C7 1.475(5) . ? C7 C8 1.385(6) . ? C7 C12 1.397(6) . ? C8 C9 1.382(6) . ? C8 H8A 0.9300 . ? C9 C10 1.375(8) . ? C9 H9A 0.9300 . ? C10 C11 1.371(8) . ? C10 H10A 0.9300 . ? C11 C12 1.384(6) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.382(5) . ? C13 C18 1.390(5) . ? C13 N1 1.425(4) . ? C14 C15 1.370(5) . ? C14 H14A 0.9300 . ? C15 C16 1.398(5) . ? C15 H15A 0.9300 . ? C16 O4 1.353(4) . ? C16 C17 1.375(5) . ? C17 C18 1.357(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 O4 1.405(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.371(6) . ? C20 C25 1.392(6) . ? C20 H20A 0.9300 . ? C21 C22 1.377(7) . ? C21 H21A 0.9300 . ? C22 C23 1.379(8) . ? C22 H22A 0.9300 . ? C23 C24 1.365(6) . ? C23 H23A 0.9300 . ? C24 C25 1.399(5) . ? C24 H24A 0.9300 . ? C25 C26 1.472(5) . ? C26 C27 1.361(5) . ? C26 N1 1.389(4) . ? C27 H27A 0.9300 . ? 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 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 108.3(4) . . ? O2 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? O2 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? O1 C3 O2 124.1(3) . . ? O1 C3 C4 122.3(4) . . ? O2 C3 C4 113.5(3) . . ? C5 C4 C27 107.8(3) . . ? C5 C4 C3 129.6(3) . . ? C27 C4 C3 122.4(3) . . ? N1 C5 C4 106.9(3) . . ? N1 C5 C6 120.9(3) . . ? C4 C5 C6 132.0(3) . . ? O3 C6 C7 120.1(3) . . ? O3 C6 C5 118.7(3) . . ? C7 C6 C5 121.2(3) . . ? C8 C7 C12 119.2(4) . . ? C8 C7 C6 120.1(4) . . ? C12 C7 C6 120.6(4) . . ? C9 C8 C7 121.0(4) . . ? C9 C8 H8A 119.5 . . ? C7 C8 H8A 119.5 . . ? C10 C9 C8 119.3(5) . . ? C10 C9 H9A 120.4 . . ? C8 C9 H9A 120.4 . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C10 C11 C12 121.0(5) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C11 C12 C7 119.1(4) . . ? C11 C12 H12A 120.5 . . ? C7 C12 H12A 120.5 . . ? C14 C13 C18 118.9(3) . . ? C14 C13 N1 121.5(3) . . ? C18 C13 N1 119.4(3) . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? O4 C16 C17 117.1(3) . . ? O4 C16 C15 124.5(3) . . ? C17 C16 C15 118.3(3) . . ? C18 C17 C16 121.6(3) . . ? C18 C17 H17A 119.2 . . ? C16 C17 H17A 119.2 . . ? C17 C18 C13 120.3(3) . . ? C17 C18 H18A 119.9 . . ? C13 C18 H18A 119.9 . . ? O4 C19 H19A 109.5 . . ? O4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 120.2(4) . . ? C21 C20 H20A 119.9 . . ? C25 C20 H20A 119.9 . . ? C20 C21 C22 120.5(4) . . ? C20 C21 H21A 119.7 . . ? C22 C21 H21A 119.7 . . ? C21 C22 C23 119.9(4) . . ? C21 C22 H22A 120.1 . . ? C23 C22 H22A 120.1 . . ? C24 C23 C22 120.2(5) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C25 120.7(4) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C20 C25 C24 118.5(4) . . ? C20 C25 C26 122.9(3) . . ? C24 C25 C26 118.4(3) . . ? C27 C26 N1 107.8(3) . . ? C27 C26 C25 128.6(3) . . ? N1 C26 C25 123.6(3) . . ? C26 C27 C4 108.5(3) . . ? C26 C27 H27A 125.8 . . ? C4 C27 H27A 125.8 . . ? C5 N1 C26 109.1(3) . . ? C5 N1 C13 126.0(3) . . ? C26 N1 C13 124.9(3) . . ? C3 O2 C2 117.9(3) . . ? C16 O4 C19 119.2(3) . . ? # Attachment '- 6a-CIF.txt' data_101116_mzj1029 _database_code_depnum_ccdc_archive 'CCDC 801307' #TrackingRef '- 6a-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H27 N O2' _chemical_formula_sum 'C38 H27 N O2' _chemical_formula_weight 529.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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/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 12.5289(4) _cell_length_b 46.5485(11) _cell_length_c 10.4955(5) _cell_angle_alpha 90.00 _cell_angle_beta 113.316(5) _cell_angle_gamma 90.00 _cell_volume 5621.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9405 _cell_measurement_theta_min 2.8460 _cell_measurement_theta_max 67.0178 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 0.600 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_process_details ; CrysAlis PRO (Oxford Diffraction, 2009) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48239 _diffrn_reflns_av_R_equivalents 0.0659 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -55 _diffrn_reflns_limit_k_max 54 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 67.13 _reflns_number_total 10013 _reflns_number_gt 6761 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2009)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+1.2113P] 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 10013 _refine_ls_number_parameters 741 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.76374(16) 0.08191(4) 0.9154(3) 0.0874(7) Uani 1 1 d . . . O2 O 1.15907(14) 0.05852(4) 0.7951(2) 0.0698(5) Uani 1 1 d . . . O3 O 0.34646(16) 0.17177(4) 1.0510(2) 0.0738(5) Uani 1 1 d . . . O4 O 0.6827(2) 0.19810(7) 0.8439(3) 0.1250(10) Uani 1 1 d . . . N1 N 0.72883(14) 0.02523(3) 0.7875(2) 0.0460(4) Uani 1 1 d . . . N2 N 0.29931(14) 0.23033(4) 0.9525(2) 0.0459(4) Uani 1 1 d . . . C1 C 0.3998(2) -0.08354(5) 0.5226(3) 0.0600(6) Uani 1 1 d . . . H1 H 0.3966 -0.0700 0.4561 0.072 Uiso 1 1 calc R . . C2 C 0.3302(2) -0.10758(6) 0.4832(3) 0.0758(8) Uani 1 1 d . . . H2 H 0.2807 -0.1100 0.3906 0.091 Uiso 1 1 calc R . . C3 C 0.3330(2) -0.12788(6) 0.5783(3) 0.0697(8) Uani 1 1 d . . . H3 H 0.2845 -0.1438 0.5514 0.084 Uiso 1 1 calc R . . C4 C 0.4079(3) -0.12446(5) 0.7133(3) 0.0676(7) Uani 1 1 d . . . H4 H 0.4117 -0.1384 0.7784 0.081 Uiso 1 1 calc R . . C5 C 0.4786(2) -0.10026(5) 0.7545(3) 0.0601(6) Uani 1 1 d . . . H5 H 0.5293 -0.0982 0.8468 0.072 Uiso 1 1 calc R . . C6 C 0.47405(17) -0.07926(4) 0.6591(2) 0.0443(5) Uani 1 1 d . . . C7 C 0.54626(17) -0.05247(4) 0.6981(2) 0.0422(5) Uani 1 1 d . . . C8 C 0.50239(17) -0.02752(4) 0.7270(2) 0.0425(5) Uani 1 1 d . . . C9 C 0.57270(17) -0.00219(4) 0.7563(2) 0.0430(5) Uani 1 1 d . . . C10 C 0.68366(17) -0.00215(4) 0.7541(2) 0.0418(5) Uani 1 1 d . . . C11 C 0.73195(16) -0.02766(4) 0.7208(2) 0.0400(5) Uani 1 1 d . . . C12 C 0.66105(17) -0.05289(4) 0.6952(2) 0.0415(5) Uani 1 1 d . . . C13 C 0.70539(18) -0.07842(5) 0.6626(3) 0.0500(5) Uani 1 1 d . . . H13 H 0.6604 -0.0950 0.6448 0.060 Uiso 1 1 calc R . . C14 C 0.81241(19) -0.07961(5) 0.6564(3) 0.0560(6) Uani 1 1 d . . . H14 H 0.8395 -0.0968 0.6353 0.067 Uiso 1 1 calc R . . C15 C 0.88023(19) -0.05505(5) 0.6818(3) 0.0530(6) Uani 1 1 d . . . H15 H 0.9529 -0.0558 0.6774 0.064 Uiso 1 1 calc R . . C16 C 0.84126(18) -0.02973(4) 0.7130(2) 0.0478(5) Uani 1 1 d . . . H16 H 0.8880 -0.0135 0.7296 0.057 Uiso 1 1 calc R . . C17 C 0.38253(17) -0.02464(4) 0.7242(2) 0.0440(5) Uani 1 1 d . . . C18 C 0.3436(2) -0.04059(5) 0.8088(3) 0.0591(6) Uani 1 1 d . . . H18 H 0.3924 -0.0541 0.8691 0.071 Uiso 1 1 calc R . . C19 C 0.2329(2) -0.03657(6) 0.8044(3) 0.0724(8) Uani 1 1 d . . . H19 H 0.2076 -0.0476 0.8610 0.087 Uiso 1 1 calc R . . C20 C 0.1604(2) -0.01664(6) 0.7179(3) 0.0690(7) Uani 1 1 d . . . H20 H 0.0862 -0.0140 0.7162 0.083 Uiso 1 1 calc R . . C21 C 0.1966(2) -0.00054(6) 0.6335(3) 0.0623(6) Uani 1 1 d . . . H21 H 0.1473 0.0131 0.5746 0.075 Uiso 1 1 calc R . . C22 C 0.30683(19) -0.00459(5) 0.6359(3) 0.0528(6) Uani 1 1 d . . . H22 H 0.3306 0.0063 0.5775 0.063 Uiso 1 1 calc R . . C23 C 0.55077(18) 0.02584(4) 0.7905(2) 0.0484(5) Uani 1 1 d . . . H23 H 0.4835 0.0320 0.7996 0.058 Uiso 1 1 calc R . . C24 C 0.64560(18) 0.04246(4) 0.8081(2) 0.0484(5) Uani 1 1 d . . . C25 C 0.6659(2) 0.07259(5) 0.8540(3) 0.0566(6) Uani 1 1 d . . . C26 C 0.5628(2) 0.09128(5) 0.8297(3) 0.0531(6) Uani 1 1 d . . . C27 C 0.4559(2) 0.08795(5) 0.7198(3) 0.0646(7) Uani 1 1 d . . . H27 H 0.4452 0.0732 0.6562 0.077 Uiso 1 1 calc R . . C28 C 0.3657(3) 0.10631(7) 0.7042(3) 0.0820(9) Uani 1 1 d . . . H28 H 0.2941 0.1038 0.6306 0.098 Uiso 1 1 calc R . . C29 C 0.3807(3) 0.12843(7) 0.7969(4) 0.0909(10) Uani 1 1 d . . . H29 H 0.3192 0.1407 0.7861 0.109 Uiso 1 1 calc R . . C30 C 0.4852(3) 0.13226(6) 0.9040(3) 0.0858(9) Uani 1 1 d . . . H30 H 0.4950 0.1473 0.9661 0.103 Uiso 1 1 calc R . . C31 C 0.5771(3) 0.11406(5) 0.9215(3) 0.0699(7) Uani 1 1 d . . . H31 H 0.6486 0.1170 0.9946 0.084 Uiso 1 1 calc R . . C32 C 0.85179(19) 0.04409(5) 0.6740(2) 0.0498(5) Uani 1 1 d . . . H32 H 0.7867 0.0451 0.5909 0.060 Uiso 1 1 calc R . . C33 C 0.9596(2) 0.05185(5) 0.6782(3) 0.0542(6) Uani 1 1 d . . . H33 H 0.9668 0.0582 0.5979 0.065 Uiso 1 1 calc R . . C34 C 1.05661(19) 0.05027(5) 0.8010(3) 0.0498(5) Uani 1 1 d . . . C35 C 1.04541(19) 0.04066(5) 0.9196(2) 0.0525(6) Uani 1 1 d . . . H35 H 1.1106 0.0392 1.0024 0.063 Uiso 1 1 calc R . . C36 C 0.93681(18) 0.03321(5) 0.9149(2) 0.0484(5) Uani 1 1 d . . . H36 H 0.9294 0.0271 0.9953 0.058 Uiso 1 1 calc R . . C37 C 0.84045(17) 0.03475(4) 0.7934(2) 0.0434(5) Uani 1 1 d . . . C38 C 1.2630(2) 0.05504(9) 0.9154(4) 0.0947(11) Uani 1 1 d . . . H38C H 1.3279 0.0615 0.8963 0.142 Uiso 1 1 calc R . . H38A H 1.2731 0.0351 0.9412 0.142 Uiso 1 1 calc R . . H38B H 1.2582 0.0661 0.9901 0.142 Uiso 1 1 calc R . . C39 C 0.0009(2) 0.34735(5) 0.7782(3) 0.0619(6) Uani 1 1 d . . . H39 H 0.0051 0.3385 0.7009 0.074 Uiso 1 1 calc R . . C40 C -0.0647(2) 0.37216(6) 0.7612(4) 0.0772(9) Uani 1 1 d . . . H40 H -0.1049 0.3796 0.6728 0.093 Uiso 1 1 calc R . . C41 C -0.0704(3) 0.38564(6) 0.8737(5) 0.0868(11) Uani 1 1 d . . . H41 H -0.1151 0.4021 0.8622 0.104 Uiso 1 1 calc R . . C42 C -0.0099(3) 0.37471(6) 1.0039(4) 0.0851(10) Uani 1 1 d . . . H42 H -0.0122 0.3841 1.0809 0.102 Uiso 1 1 calc R . . C43 C 0.0547(2) 0.34974(5) 1.0214(3) 0.0644(7) Uani 1 1 d . . . H43 H 0.0948 0.3425 1.1102 0.077 Uiso 1 1 calc R . . C44 C 0.06038(18) 0.33547(4) 0.9087(3) 0.0485(5) Uani 1 1 d . . . C45 C 0.12748(17) 0.30828(4) 0.9252(2) 0.0428(5) Uani 1 1 d . . . C46 C 0.08772(16) 0.28273(4) 0.9556(2) 0.0404(5) Uani 1 1 d . . . C47 C 0.15395(17) 0.25713(4) 0.9642(2) 0.0403(4) Uani 1 1 d . . . C48 C 0.25662(17) 0.25800(4) 0.9407(2) 0.0414(5) Uani 1 1 d . . . C49 C 0.30223(18) 0.28425(4) 0.9119(2) 0.0441(5) Uani 1 1 d . . . C50 C 0.23713(18) 0.30951(4) 0.9084(2) 0.0454(5) Uani 1 1 d . . . C51 C 0.2851(2) 0.33620(5) 0.8958(3) 0.0591(6) Uani 1 1 d . . . H51 H 0.2445 0.3529 0.8955 0.071 Uiso 1 1 calc R . . C52 C 0.3891(2) 0.33818(5) 0.8839(3) 0.0712(8) Uani 1 1 d . . . H52 H 0.4202 0.3561 0.8792 0.085 Uiso 1 1 calc R . . C53 C 0.4488(2) 0.31339(5) 0.8789(3) 0.0706(8) Uani 1 1 d . . . H53 H 0.5179 0.3148 0.8660 0.085 Uiso 1 1 calc R . . C54 C 0.4071(2) 0.28707(5) 0.8926(3) 0.0593(6) Uani 1 1 d . . . H54 H 0.4484 0.2707 0.8891 0.071 Uiso 1 1 calc R . . C55 C -0.02063(17) 0.28075(4) 0.9827(2) 0.0425(5) Uani 1 1 d . . . C56 C -0.12691(19) 0.29034(5) 0.8875(3) 0.0549(6) Uani 1 1 d . . . H56 H -0.1323 0.2975 0.8024 0.066 Uiso 1 1 calc R . . C57 C -0.2249(2) 0.28941(6) 0.9169(3) 0.0714(8) Uani 1 1 d . . . H57 H -0.2956 0.2959 0.8516 0.086 Uiso 1 1 calc R . . C58 C -0.2189(2) 0.27891(7) 1.0423(4) 0.0773(8) Uani 1 1 d . . . H58 H -0.2848 0.2784 1.0623 0.093 Uiso 1 1 calc R . . C59 C -0.1138(2) 0.26912(6) 1.1379(3) 0.0705(7) Uani 1 1 d . . . H59 H -0.1088 0.2621 1.2230 0.085 Uiso 1 1 calc R . . C60 C -0.0157(2) 0.26967(5) 1.1079(3) 0.0538(6) Uani 1 1 d . . . H60 H 0.0543 0.2625 1.1722 0.065 Uiso 1 1 calc R . . C61 C 0.13411(18) 0.22803(4) 0.9869(2) 0.0463(5) Uani 1 1 d . . . H61 H 0.0716 0.2210 1.0041 0.056 Uiso 1 1 calc R . . C62 C 0.22301(18) 0.21198(4) 0.9791(2) 0.0474(5) Uani 1 1 d . . . C63 C 0.2471(2) 0.18089(5) 1.0028(3) 0.0520(6) Uani 1 1 d . . . C64 C 0.1469(2) 0.16088(4) 0.9659(3) 0.0525(6) Uani 1 1 d . . . C65 C 0.0422(2) 0.16628(5) 0.8592(3) 0.0648(7) Uani 1 1 d . . . H65 H 0.0303 0.1836 0.8113 0.078 Uiso 1 1 calc R . . C66 C -0.0460(3) 0.14604(7) 0.8223(4) 0.0856(9) Uani 1 1 d . . . H66 H -0.1164 0.1496 0.7485 0.103 Uiso 1 1 calc R . . C67 C -0.0293(3) 0.12072(7) 0.8948(4) 0.0901(10) Uani 1 1 d . . . H67 H -0.0889 0.1073 0.8712 0.108 Uiso 1 1 calc R . . C68 C 0.0744(4) 0.11535(6) 1.0011(4) 0.0918(11) Uani 1 1 d . . . H68 H 0.0852 0.0982 1.0504 0.110 Uiso 1 1 calc R . . C69 C 0.1632(3) 0.13486(5) 1.0364(3) 0.0720(7) Uani 1 1 d . . . H69 H 0.2345 0.1307 1.1076 0.086 Uiso 1 1 calc R . . C70 C 0.39997(17) 0.22128(4) 0.9284(2) 0.0448(5) Uani 1 1 d . . . C71 C 0.3872(2) 0.21282(6) 0.7978(3) 0.0605(6) Uani 1 1 d . . . H71 H 0.3139 0.2125 0.7259 0.073 Uiso 1 1 calc R . . C72 C 0.4833(3) 0.20484(7) 0.7735(3) 0.0789(8) Uani 1 1 d . . . H72 H 0.4743 0.1988 0.6854 0.095 Uiso 1 1 calc R . . C73 C 0.5918(2) 0.20578(7) 0.8776(3) 0.0739(8) Uani 1 1 d . . . C74 C 0.6047(2) 0.21387(6) 1.0091(3) 0.0709(8) Uani 1 1 d . . . H74 H 0.6781 0.2142 1.0809 0.085 Uiso 1 1 calc R . . C75 C 0.5074(2) 0.22157(5) 1.0343(3) 0.0580(6) Uani 1 1 d . . . H75 H 0.5156 0.2269 1.1231 0.070 Uiso 1 1 calc R . . C76 C 0.7927(4) 0.19788(14) 0.9431(7) 0.170(2) Uani 1 1 d . . . H76A H 0.8453 0.1910 0.9038 0.254 Uiso 1 1 calc R . . H76B H 0.7961 0.1855 1.0177 0.254 Uiso 1 1 calc R . . H76C H 0.8144 0.2170 0.9780 0.254 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 0.0602(11) 0.0571(11) 0.151(2) -0.0371(12) 0.0488(12) -0.0190(9) O2 0.0487(10) 0.0868(12) 0.0804(12) 0.0004(10) 0.0327(9) -0.0155(9) O3 0.0613(11) 0.0523(10) 0.1143(16) 0.0118(10) 0.0416(11) 0.0144(8) O4 0.0607(14) 0.183(3) 0.142(2) -0.025(2) 0.0507(15) 0.0280(15) N1 0.0392(9) 0.0361(9) 0.0655(12) -0.0033(8) 0.0235(9) -0.0024(7) N2 0.0408(9) 0.0373(9) 0.0647(12) 0.0000(8) 0.0264(9) 0.0040(7) C1 0.0483(13) 0.0524(13) 0.0689(16) 0.0039(12) 0.0121(12) -0.0048(11) C2 0.0567(15) 0.0624(16) 0.087(2) -0.0081(15) 0.0053(14) -0.0143(13) C3 0.0485(14) 0.0489(14) 0.113(2) -0.0150(15) 0.0329(16) -0.0119(11) C4 0.0807(18) 0.0446(13) 0.095(2) -0.0002(13) 0.0533(18) -0.0090(12) C5 0.0694(16) 0.0492(13) 0.0663(16) -0.0007(11) 0.0316(13) -0.0078(11) C6 0.0347(11) 0.0391(11) 0.0634(14) -0.0018(10) 0.0240(10) 0.0001(8) C7 0.0354(10) 0.0402(11) 0.0513(12) -0.0010(9) 0.0173(9) -0.0009(8) C8 0.0363(10) 0.0434(11) 0.0496(12) -0.0008(9) 0.0187(9) -0.0017(8) C9 0.0375(11) 0.0407(11) 0.0523(12) -0.0020(9) 0.0194(9) -0.0013(8) C10 0.0371(11) 0.0363(10) 0.0525(12) -0.0011(9) 0.0182(9) -0.0027(8) C11 0.0341(10) 0.0375(10) 0.0482(12) 0.0011(8) 0.0161(9) 0.0008(8) C12 0.0366(11) 0.0382(10) 0.0496(12) 0.0013(9) 0.0169(9) 0.0015(8) C13 0.0405(12) 0.0388(11) 0.0703(15) -0.0036(10) 0.0217(11) -0.0015(9) C14 0.0452(13) 0.0415(12) 0.0846(18) -0.0060(11) 0.0291(12) 0.0040(10) C15 0.0394(12) 0.0516(13) 0.0754(16) -0.0022(11) 0.0306(11) 0.0015(10) C16 0.0409(11) 0.0402(11) 0.0653(14) -0.0011(10) 0.0242(11) -0.0027(9) C17 0.0382(11) 0.0401(11) 0.0564(13) -0.0078(9) 0.0217(10) -0.0041(9) C18 0.0555(14) 0.0568(14) 0.0737(17) 0.0051(12) 0.0347(13) 0.0014(11) C19 0.0652(17) 0.0707(17) 0.101(2) 0.0032(16) 0.0542(16) -0.0067(14) C20 0.0431(13) 0.0703(17) 0.102(2) -0.0121(15) 0.0378(14) -0.0021(12) C21 0.0403(13) 0.0641(15) 0.0794(18) -0.0025(13) 0.0205(12) 0.0050(11) C22 0.0426(12) 0.0551(13) 0.0623(15) -0.0002(11) 0.0224(11) -0.0006(10) C23 0.0395(11) 0.0432(11) 0.0658(15) -0.0072(10) 0.0242(10) -0.0004(9) C24 0.0438(12) 0.0405(11) 0.0621(14) -0.0043(10) 0.0222(11) -0.0006(9) C25 0.0552(14) 0.0427(12) 0.0809(17) -0.0074(11) 0.0364(13) -0.0067(10) C26 0.0621(15) 0.0385(11) 0.0670(15) 0.0002(10) 0.0342(13) 0.0009(10) C27 0.0713(17) 0.0507(14) 0.0721(17) -0.0042(12) 0.0288(14) 0.0092(12) C28 0.0798(19) 0.0757(19) 0.081(2) 0.0003(16) 0.0220(16) 0.0248(16) C29 0.096(2) 0.078(2) 0.092(2) -0.0023(17) 0.031(2) 0.0420(18) C30 0.105(2) 0.0665(18) 0.084(2) -0.0143(15) 0.036(2) 0.0265(17) C31 0.0788(18) 0.0531(14) 0.0793(19) -0.0096(13) 0.0329(15) 0.0063(13) C32 0.0454(12) 0.0457(12) 0.0538(13) 0.0022(10) 0.0150(10) -0.0025(9) C33 0.0574(14) 0.0522(13) 0.0573(14) 0.0036(11) 0.0274(12) -0.0067(11) C34 0.0442(12) 0.0455(12) 0.0637(15) -0.0034(10) 0.0256(11) -0.0080(9) C35 0.0402(12) 0.0581(13) 0.0549(14) -0.0004(11) 0.0142(10) -0.0023(10) C36 0.0461(12) 0.0486(12) 0.0535(13) 0.0035(10) 0.0229(11) -0.0018(9) C37 0.0388(11) 0.0344(10) 0.0584(13) -0.0015(9) 0.0207(10) -0.0029(8) C38 0.0443(15) 0.137(3) 0.101(2) -0.008(2) 0.0263(16) -0.0219(17) C39 0.0499(13) 0.0547(14) 0.0803(18) 0.0090(13) 0.0249(13) 0.0062(11) C40 0.0519(15) 0.0615(16) 0.116(3) 0.0288(17) 0.0306(16) 0.0120(13) C41 0.0701(19) 0.0503(15) 0.165(4) 0.025(2) 0.073(2) 0.0182(13) C42 0.105(2) 0.0500(15) 0.134(3) -0.0081(18) 0.083(2) 0.0066(16) C43 0.0685(16) 0.0502(13) 0.0876(19) -0.0021(13) 0.0449(15) 0.0036(12) C44 0.0398(11) 0.0396(11) 0.0717(16) 0.0033(10) 0.0280(11) 0.0011(9) C45 0.0374(11) 0.0388(11) 0.0537(13) -0.0002(9) 0.0197(10) 0.0014(8) C46 0.0337(10) 0.0400(11) 0.0474(12) -0.0029(9) 0.0158(9) 0.0014(8) C47 0.0354(10) 0.0395(10) 0.0466(12) -0.0028(9) 0.0168(9) 0.0003(8) C48 0.0365(10) 0.0377(10) 0.0512(12) -0.0020(9) 0.0185(9) 0.0012(8) C49 0.0405(11) 0.0406(11) 0.0555(13) 0.0018(9) 0.0235(10) 0.0011(9) C50 0.0417(11) 0.0407(11) 0.0565(13) 0.0038(9) 0.0222(10) 0.0022(9) C51 0.0514(13) 0.0403(12) 0.0940(19) 0.0095(12) 0.0378(13) 0.0053(10) C52 0.0592(15) 0.0457(13) 0.125(2) 0.0168(14) 0.0534(16) 0.0013(11) C53 0.0546(15) 0.0565(14) 0.121(2) 0.0172(15) 0.0567(16) 0.0048(12) C54 0.0519(14) 0.0476(13) 0.0921(19) 0.0073(12) 0.0431(14) 0.0062(10) C55 0.0373(11) 0.0372(10) 0.0557(13) -0.0045(9) 0.0214(10) -0.0024(8) C56 0.0400(12) 0.0609(14) 0.0634(15) -0.0003(11) 0.0199(11) 0.0009(10) C57 0.0407(13) 0.0782(18) 0.096(2) 0.0039(16) 0.0282(14) 0.0032(12) C58 0.0528(16) 0.0854(19) 0.113(3) -0.0006(18) 0.0539(18) -0.0045(14) C59 0.0733(18) 0.0740(17) 0.0809(19) 0.0046(14) 0.0484(16) -0.0094(14) C60 0.0474(13) 0.0545(13) 0.0648(15) 0.0020(11) 0.0277(11) -0.0016(10) C61 0.0416(11) 0.0405(11) 0.0603(14) -0.0010(10) 0.0240(10) -0.0021(9) C62 0.0444(12) 0.0396(11) 0.0614(14) -0.0016(10) 0.0243(11) -0.0017(9) C63 0.0529(14) 0.0414(12) 0.0688(15) 0.0008(10) 0.0318(12) 0.0051(10) C64 0.0654(15) 0.0364(11) 0.0651(15) -0.0053(10) 0.0358(13) -0.0016(10) C65 0.0687(17) 0.0474(13) 0.0816(19) -0.0080(12) 0.0332(15) -0.0089(12) C66 0.0781(19) 0.0699(19) 0.106(2) -0.0216(17) 0.0339(18) -0.0193(15) C67 0.109(3) 0.069(2) 0.111(3) -0.0289(19) 0.063(2) -0.0436(19) C68 0.146(3) 0.0538(16) 0.091(2) -0.0094(16) 0.063(3) -0.0316(19) C69 0.100(2) 0.0435(13) 0.0771(18) -0.0015(12) 0.0397(16) -0.0075(14) C70 0.0385(11) 0.0392(11) 0.0603(14) 0.0015(9) 0.0233(10) 0.0047(8) C71 0.0504(13) 0.0719(16) 0.0588(15) -0.0007(12) 0.0212(12) 0.0130(12) C72 0.0680(18) 0.107(2) 0.0696(18) -0.0061(16) 0.0353(16) 0.0218(16) C73 0.0558(16) 0.088(2) 0.086(2) 0.0002(16) 0.0372(16) 0.0180(14) C74 0.0396(13) 0.0805(18) 0.085(2) 0.0011(15) 0.0169(13) 0.0063(12) C75 0.0459(13) 0.0663(15) 0.0590(15) -0.0063(12) 0.0176(12) 0.0026(11) C76 0.088(3) 0.217(6) 0.217(6) -0.048(5) 0.074(4) 0.022(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C25 1.217(3) . ? O2 C34 1.365(3) . ? O2 C38 1.419(4) . ? O3 C63 1.219(3) . ? O4 C76 1.360(5) . ? O4 C73 1.367(3) . ? N1 C10 1.382(3) . ? N1 C24 1.398(3) . ? N1 C37 1.445(3) . ? N2 C48 1.381(3) . ? N2 C62 1.391(3) . ? N2 C70 1.444(3) . ? C1 C2 1.377(3) . ? C1 C6 1.379(3) . ? C1 H1 0.9300 . ? C2 C3 1.364(4) . ? C2 H2 0.9300 . ? C3 C4 1.365(4) . ? C3 H3 0.9300 . ? C4 C5 1.392(3) . ? C4 H4 0.9300 . ? C5 C6 1.385(3) . ? C5 H5 0.9300 . ? C6 C7 1.500(3) . ? C7 C8 1.369(3) . ? C7 C12 1.451(3) . ? C8 C9 1.431(3) . ? C8 C17 1.497(3) . ? C9 C10 1.399(3) . ? C9 C23 1.409(3) . ? C10 C11 1.437(3) . ? C11 C16 1.407(3) . ? C11 C12 1.432(3) . ? C12 C13 1.410(3) . ? C13 C14 1.369(3) . ? C13 H13 0.9300 . ? C14 C15 1.386(3) . ? C14 H14 0.9300 . ? C15 C16 1.365(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.386(3) . ? C17 C22 1.391(3) . ? C18 C19 1.382(3) . ? C18 H18 0.9300 . ? C19 C20 1.363(4) . ? C19 H19 0.9300 . ? C20 C21 1.368(4) . ? C20 H20 0.9300 . ? C21 C22 1.384(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.368(3) . ? C23 H23 0.9300 . ? C24 C25 1.472(3) . ? C25 C26 1.493(3) . ? C26 C27 1.388(4) . ? C26 C31 1.396(3) . ? C27 C28 1.374(4) . ? C27 H27 0.9300 . ? C28 C29 1.378(4) . ? C28 H28 0.9300 . ? C29 C30 1.359(5) . ? C29 H29 0.9300 . ? C30 C31 1.382(4) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C33 1.381(3) . ? C32 C37 1.385(3) . ? C32 H32 0.9300 . ? C33 C34 1.380(3) . ? C33 H33 0.9300 . ? C34 C35 1.381(3) . ? C35 C36 1.386(3) . ? C35 H35 0.9300 . ? C36 C37 1.368(3) . ? C36 H36 0.9300 . ? C38 H38C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C39 C40 1.388(4) . ? C39 C44 1.388(3) . ? C39 H39 0.9300 . ? C40 C41 1.364(5) . ? C40 H40 0.9300 . ? C41 C42 1.371(5) . ? C41 H41 0.9300 . ? C42 C43 1.386(4) . ? C42 H42 0.9300 . ? C43 C44 1.383(3) . ? C43 H43 0.9300 . ? C44 C45 1.491(3) . ? C45 C46 1.375(3) . ? C45 C50 1.454(3) . ? C46 C47 1.434(3) . ? C46 C55 1.496(3) . ? C47 C48 1.403(3) . ? C47 C61 1.415(3) . ? C48 C49 1.431(3) . ? C49 C54 1.413(3) . ? C49 C50 1.423(3) . ? C50 C51 1.409(3) . ? C51 C52 1.360(3) . ? C51 H51 0.9300 . ? C52 C53 1.387(4) . ? C52 H52 0.9300 . ? C53 C54 1.361(3) . ? C53 H53 0.9300 . ? C54 H54 0.9300 . ? C55 C56 1.385(3) . ? C55 C60 1.390(3) . ? C56 C57 1.380(3) . ? C56 H56 0.9300 . ? C57 C58 1.378(4) . ? C57 H57 0.9300 . ? C58 C59 1.379(4) . ? C58 H58 0.9300 . ? C59 C60 1.384(3) . ? C59 H59 0.9300 . ? C60 H60 0.9300 . ? C61 C62 1.370(3) . ? C61 H61 0.9300 . ? C62 C63 1.479(3) . ? C63 C64 1.487(3) . ? C64 C65 1.369(4) . ? C64 C69 1.391(3) . ? C65 C66 1.386(4) . ? C65 H65 0.9300 . ? C66 C67 1.373(5) . ? C66 H66 0.9300 . ? C67 C68 1.360(5) . ? C67 H67 0.9300 . ? C68 C69 1.368(4) . ? C68 H68 0.9300 . ? C69 H69 0.9300 . ? C70 C75 1.365(3) . ? C70 C71 1.373(3) . ? C71 C72 1.377(4) . ? C71 H71 0.9300 . ? C72 C73 1.367(4) . ? C72 H72 0.9300 . ? C73 C74 1.377(4) . ? C74 C75 1.393(4) . ? C74 H74 0.9300 . ? C75 H75 0.9300 . ? C76 H76A 0.9600 . ? C76 H76B 0.9600 . ? C76 H76C 0.9600 . ? 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 C34 O2 C38 118.4(2) . . ? C76 O4 C73 120.0(3) . . ? C10 N1 C24 108.23(16) . . ? C10 N1 C37 125.84(17) . . ? C24 N1 C37 125.87(16) . . ? C48 N2 C62 108.57(16) . . ? C48 N2 C70 126.18(17) . . ? C62 N2 C70 125.01(17) . . ? C2 C1 C6 121.0(3) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 120.9(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.2(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C1 C6 C5 117.8(2) . . ? C1 C6 C7 119.4(2) . . ? C5 C6 C7 122.8(2) . . ? C8 C7 C12 120.29(18) . . ? C8 C7 C6 120.96(17) . . ? C12 C7 C6 118.61(17) . . ? C7 C8 C9 118.66(18) . . ? C7 C8 C17 124.03(18) . . ? C9 C8 C17 117.26(17) . . ? C10 C9 C23 107.35(17) . . ? C10 C9 C8 121.93(18) . . ? C23 C9 C8 130.73(19) . . ? N1 C10 C9 107.84(17) . . ? N1 C10 C11 130.86(18) . . ? C9 C10 C11 121.29(17) . . ? C16 C11 C12 118.61(18) . . ? C16 C11 C10 125.71(18) . . ? C12 C11 C10 115.68(17) . . ? C13 C12 C11 117.49(18) . . ? C13 C12 C7 120.37(18) . . ? C11 C12 C7 122.11(18) . . ? C14 C13 C12 122.2(2) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 119.7(2) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.5(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 121.47(19) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C18 C17 C22 117.8(2) . . ? C18 C17 C8 123.0(2) . . ? C22 C17 C8 119.19(19) . . ? C19 C18 C17 120.6(2) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 120.7(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 120.0(2) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C22 119.9(2) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C21 C22 C17 121.1(2) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? C24 C23 C9 108.15(19) . . ? C24 C23 H23 125.9 . . ? C9 C23 H23 125.9 . . ? C23 C24 N1 108.41(18) . . ? C23 C24 C25 127.7(2) . . ? N1 C24 C25 123.66(19) . . ? O1 C25 C24 121.3(2) . . ? O1 C25 C26 120.3(2) . . ? C24 C25 C26 118.3(2) . . ? C27 C26 C31 118.5(2) . . ? C27 C26 C25 124.2(2) . . ? C31 C26 C25 117.3(2) . . ? C28 C27 C26 120.5(3) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C29 120.3(3) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C30 C29 C28 120.0(3) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 120.6(3) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C30 C31 C26 120.1(3) . . ? C30 C31 H31 120.0 . . ? C26 C31 H31 120.0 . . ? C33 C32 C37 120.1(2) . . ? C33 C32 H32 119.9 . . ? C37 C32 H32 119.9 . . ? C34 C33 C32 120.3(2) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? O2 C34 C33 116.1(2) . . ? O2 C34 C35 124.4(2) . . ? C33 C34 C35 119.5(2) . . ? C34 C35 C36 119.8(2) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C37 C36 C35 120.8(2) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C36 C37 C32 119.41(19) . . ? C36 C37 N1 120.4(2) . . ? C32 C37 N1 120.12(19) . . ? O2 C38 H38C 109.5 . . ? O2 C38 H38A 109.5 . . ? H38C C38 H38A 109.5 . . ? O2 C38 H38B 109.5 . . ? H38C C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C40 C39 C44 121.2(3) . . ? C40 C39 H39 119.4 . . ? C44 C39 H39 119.4 . . ? C41 C40 C39 120.2(3) . . ? C41 C40 H40 119.9 . . ? C39 C40 H40 119.9 . . ? C40 C41 C42 119.6(3) . . ? C40 C41 H41 120.2 . . ? C42 C41 H41 120.2 . . ? C41 C42 C43 120.5(3) . . ? C41 C42 H42 119.8 . . ? C43 C42 H42 119.8 . . ? C44 C43 C42 120.9(3) . . ? C44 C43 H43 119.5 . . ? C42 C43 H43 119.5 . . ? C43 C44 C39 117.6(2) . . ? C43 C44 C45 121.7(2) . . ? C39 C44 C45 120.7(2) . . ? C46 C45 C50 120.59(18) . . ? C46 C45 C44 121.47(18) . . ? C50 C45 C44 117.93(17) . . ? C45 C46 C47 118.64(18) . . ? C45 C46 C55 122.47(17) . . ? C47 C46 C55 118.88(17) . . ? C48 C47 C61 106.95(17) . . ? C48 C47 C46 120.88(18) . . ? C61 C47 C46 132.09(19) . . ? N2 C48 C47 107.88(17) . . ? N2 C48 C49 129.98(18) . . ? C47 C48 C49 122.14(18) . . ? C54 C49 C50 118.40(19) . . ? C54 C49 C48 125.54(19) . . ? C50 C49 C48 116.01(18) . . ? C51 C50 C49 118.01(19) . . ? C51 C50 C45 120.32(19) . . ? C49 C50 C45 121.57(18) . . ? C52 C51 C50 121.9(2) . . ? C52 C51 H51 119.1 . . ? C50 C51 H51 119.1 . . ? C51 C52 C53 119.8(2) . . ? C51 C52 H52 120.1 . . ? C53 C52 H52 120.1 . . ? C54 C53 C52 120.7(2) . . ? C54 C53 H53 119.7 . . ? C52 C53 H53 119.7 . . ? C53 C54 C49 121.0(2) . . ? C53 C54 H54 119.5 . . ? C49 C54 H54 119.5 . . ? C56 C55 C60 118.2(2) . . ? C56 C55 C46 121.9(2) . . ? C60 C55 C46 119.87(19) . . ? C57 C56 C55 121.0(2) . . ? C57 C56 H56 119.5 . . ? C55 C56 H56 119.5 . . ? C58 C57 C56 120.5(3) . . ? C58 C57 H57 119.8 . . ? C56 C57 H57 119.8 . . ? C57 C58 C59 119.2(2) . . ? C57 C58 H58 120.4 . . ? C59 C58 H58 120.4 . . ? C58 C59 C60 120.4(3) . . ? C58 C59 H59 119.8 . . ? C60 C59 H59 119.8 . . ? C59 C60 C55 120.7(2) . . ? C59 C60 H60 119.7 . . ? C55 C60 H60 119.7 . . ? C62 C61 C47 108.13(18) . . ? C62 C61 H61 125.9 . . ? C47 C61 H61 125.9 . . ? C61 C62 N2 108.45(18) . . ? C61 C62 C63 129.8(2) . . ? N2 C62 C63 121.59(18) . . ? O3 C63 C62 121.2(2) . . ? O3 C63 C64 120.5(2) . . ? C62 C63 C64 118.3(2) . . ? C65 C64 C69 119.1(2) . . ? C65 C64 C63 122.3(2) . . ? C69 C64 C63 118.4(2) . . ? C64 C65 C66 120.2(3) . . ? C64 C65 H65 119.9 . . ? C66 C65 H65 119.9 . . ? C67 C66 C65 119.9(3) . . ? C67 C66 H66 120.0 . . ? C65 C66 H66 120.0 . . ? C68 C67 C66 119.9(3) . . ? C68 C67 H67 120.0 . . ? C66 C67 H67 120.0 . . ? C67 C68 C69 120.7(3) . . ? C67 C68 H68 119.7 . . ? C69 C68 H68 119.7 . . ? C68 C69 C64 120.1(3) . . ? C68 C69 H69 120.0 . . ? C64 C69 H69 120.0 . . ? C75 C70 C71 120.2(2) . . ? C75 C70 N2 120.1(2) . . ? C71 C70 N2 119.62(19) . . ? C70 C71 C72 119.8(2) . . ? C70 C71 H71 120.1 . . ? C72 C71 H71 120.1 . . ? C73 C72 C71 120.6(3) . . ? C73 C72 H72 119.7 . . ? C71 C72 H72 119.7 . . ? O4 C73 C72 116.8(3) . . ? O4 C73 C74 123.5(3) . . ? C72 C73 C74 119.7(2) . . ? C73 C74 C75 119.8(2) . . ? C73 C74 H74 120.1 . . ? C75 C74 H74 120.1 . . ? C70 C75 C74 119.9(2) . . ? C70 C75 H75 120.1 . . ? C74 C75 H75 120.1 . . ? O4 C76 H76A 109.5 . . ? O4 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? O4 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 67.13 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.533 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.041