# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a1 _database_code_depnum_ccdc_archive 'CCDC 905874' #TrackingRef 'cif-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 N O4' _chemical_formula_weight 385.40 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 ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8796(3) _cell_length_b 18.3527(7) _cell_length_c 7.5914(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.610(2) _cell_angle_gamma 90.00 _cell_volume 957.49(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9644 _exptl_absorpt_correction_T_max 0.9820 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11245 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.40 _reflns_number_total 3620 _reflns_number_gt 3140 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.0403P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.3(10) _refine_ls_number_reflns 3620 _refine_ls_number_parameters 264 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.26605(18) 1.13210(8) 0.7325(2) 0.0543(4) Uani 1 1 d . . . O2 O 1.3542(2) 1.01964(10) 0.8125(3) 0.0781(5) Uani 1 1 d . . . O3 O 0.9331(2) 1.10202(9) 1.0246(2) 0.0655(4) Uani 1 1 d . . . O4 O 1.3141(2) 1.02111(9) 0.3586(2) 0.0692(5) Uani 1 1 d . . . N1 N 0.8480(2) 0.88992(8) 0.67220(19) 0.0419(3) Uani 1 1 d . . . C1 C 1.4491(3) 1.15950(16) 0.8067(4) 0.0724(7) Uani 1 1 d . . . H1A H 1.4686 1.1422 0.9256 0.109 Uiso 1 1 calc R . . H1B H 1.4468 1.2118 0.8065 0.109 Uiso 1 1 calc R . . H1C H 1.5533 1.1427 0.7373 0.109 Uiso 1 1 calc R . . C2 C 1.2377(3) 1.06097(11) 0.7453(3) 0.0468(4) Uani 1 1 d . . . C3 C 1.0391(2) 1.03583(10) 0.6668(2) 0.0393(4) Uani 1 1 d . . . C4 C 1.0706(2) 0.97291(10) 0.5434(2) 0.0400(4) Uani 1 1 d . . . C5 C 0.9743(2) 0.90863(9) 0.5435(2) 0.0381(4) Uani 1 1 d . . . C6 C 0.7355(2) 0.82339(10) 0.6711(2) 0.0389(4) Uani 1 1 d . . . C7 C 0.5439(3) 0.82497(13) 0.6114(3) 0.0590(5) Uani 1 1 d . . . H7 H 0.4880 0.8681 0.5691 0.071 Uiso 1 1 calc R . . C8 C 0.4350(3) 0.76127(16) 0.6149(4) 0.0740(7) Uani 1 1 d . . . H8 H 0.3049 0.7619 0.5758 0.089 Uiso 1 1 calc R . . C9 C 0.5168(4) 0.69800(14) 0.6750(3) 0.0642(6) Uani 1 1 d . . . H9 H 0.4427 0.6556 0.6753 0.077 Uiso 1 1 calc R . . C10 C 0.8340(2) 0.93949(10) 0.8086(2) 0.0400(4) Uani 1 1 d . . . C11 C 0.7165(3) 0.92393(11) 0.9654(2) 0.0475(4) Uani 1 1 d . . . H11A H 0.7650 0.8812 1.0284 0.057 Uiso 1 1 calc R . . H11B H 0.5805 0.9166 0.9308 0.057 Uiso 1 1 calc R . . C12 C 0.7445(3) 0.99281(11) 1.0780(3) 0.0492(5) Uani 1 1 d . . . H12A H 0.6205 1.0164 1.0945 0.059 Uiso 1 1 calc R . . H12B H 0.8037 0.9808 1.1928 0.059 Uiso 1 1 calc R . . C13 C 0.8768(3) 1.04206(11) 0.9773(2) 0.0460(4) Uani 1 1 d . . . C14 C 0.9222(2) 1.00486(10) 0.8140(2) 0.0402(4) Uani 1 1 d . . . C15 C 0.7073(3) 0.69633(12) 0.7350(3) 0.0539(5) Uani 1 1 d . . . H15 H 0.7624 0.6530 0.7763 0.065 Uiso 1 1 calc R . . C16 C 0.8176(3) 0.75928(10) 0.7342(2) 0.0437(4) Uani 1 1 d . . . H16 H 0.9467 0.7585 0.7760 0.052 Uiso 1 1 calc R . . C17 C 1.0258(3) 0.86267(10) 0.3885(2) 0.0401(4) Uani 1 1 d . . . C18 C 1.1632(3) 0.90376(11) 0.2996(2) 0.0456(4) Uani 1 1 d . . . C19 C 1.1993(3) 0.97365(11) 0.3951(3) 0.0478(4) Uani 1 1 d . . . C20 C 1.2414(3) 0.87865(13) 0.1488(3) 0.0595(6) Uani 1 1 d . . . H20 H 1.3301 0.9066 0.0894 0.071 Uiso 1 1 calc R . . C21 C 1.1852(3) 0.81027(13) 0.0864(3) 0.0587(5) Uani 1 1 d . . . H21 H 1.2400 0.7916 -0.0139 0.070 Uiso 1 1 calc R . . C22 C 1.0494(3) 0.76984(12) 0.1712(3) 0.0521(5) Uani 1 1 d . . . H22 H 1.0121 0.7245 0.1264 0.062 Uiso 1 1 calc R . . C23 C 0.9667(3) 0.79595(11) 0.3241(2) 0.0454(4) Uani 1 1 d . . . H23 H 0.8739 0.7688 0.3806 0.054 Uiso 1 1 calc R . . C24 C 0.9249(3) 1.09638(10) 0.5682(3) 0.0455(4) Uani 1 1 d . . . H24A H 0.9998 1.1145 0.4740 0.068 Uiso 1 1 calc R . . H24B H 0.8995 1.1353 0.6483 0.068 Uiso 1 1 calc R . . H24C H 0.8038 1.0771 0.5205 0.068 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 0.0435(7) 0.0462(8) 0.0728(9) -0.0045(7) -0.0015(6) -0.0068(6) O2 0.0565(9) 0.0637(12) 0.1114(14) 0.0159(10) -0.0255(9) 0.0043(8) O3 0.0853(10) 0.0537(10) 0.0581(9) -0.0134(7) 0.0088(8) -0.0107(8) O4 0.0694(9) 0.0552(10) 0.0860(11) -0.0046(8) 0.0353(8) -0.0170(8) N1 0.0455(8) 0.0391(8) 0.0418(8) 0.0018(6) 0.0091(6) -0.0030(6) C1 0.0508(11) 0.0771(18) 0.0888(18) -0.0125(13) -0.0027(12) -0.0176(11) C2 0.0415(9) 0.0453(11) 0.0536(11) 0.0027(8) 0.0020(8) 0.0016(8) C3 0.0372(8) 0.0359(9) 0.0448(9) 0.0030(7) 0.0035(7) 0.0016(7) C4 0.0390(8) 0.0373(9) 0.0442(9) 0.0045(8) 0.0057(7) 0.0012(7) C5 0.0382(8) 0.0347(9) 0.0414(9) 0.0046(7) 0.0023(7) 0.0041(7) C6 0.0419(9) 0.0376(9) 0.0376(9) 0.0021(7) 0.0046(7) -0.0034(7) C7 0.0471(10) 0.0576(13) 0.0712(14) 0.0144(11) -0.0082(10) 0.0034(9) C8 0.0488(12) 0.0796(19) 0.0918(19) 0.0043(14) -0.0158(12) -0.0134(12) C9 0.0687(13) 0.0550(13) 0.0687(14) -0.0017(11) 0.0031(11) -0.0243(11) C10 0.0373(8) 0.0399(9) 0.0429(9) 0.0030(7) 0.0025(7) 0.0042(7) C11 0.0523(10) 0.0466(11) 0.0446(10) 0.0051(8) 0.0128(8) 0.0026(8) C12 0.0519(10) 0.0541(12) 0.0421(10) 0.0009(9) 0.0076(8) 0.0050(8) C13 0.0489(10) 0.0439(11) 0.0449(10) -0.0011(8) 0.0003(8) 0.0054(8) C14 0.0399(9) 0.0393(9) 0.0414(9) 0.0020(7) 0.0030(7) 0.0032(7) C15 0.0731(13) 0.0389(10) 0.0501(11) 0.0058(8) 0.0072(9) -0.0011(9) C16 0.0420(9) 0.0455(11) 0.0436(10) 0.0029(8) 0.0015(7) 0.0023(7) C17 0.0426(9) 0.0374(10) 0.0403(9) 0.0050(7) 0.0018(7) 0.0062(7) C18 0.0419(9) 0.0458(11) 0.0496(10) 0.0018(8) 0.0082(8) 0.0036(8) C19 0.0435(10) 0.0443(10) 0.0566(11) 0.0035(8) 0.0114(8) 0.0004(8) C20 0.0526(12) 0.0674(15) 0.0602(12) -0.0060(11) 0.0217(9) -0.0021(10) C21 0.0624(12) 0.0655(15) 0.0489(11) -0.0104(10) 0.0104(9) 0.0093(10) C22 0.0645(12) 0.0457(11) 0.0457(11) -0.0037(8) -0.0010(9) 0.0079(9) C23 0.0546(10) 0.0410(10) 0.0406(9) 0.0043(8) 0.0021(8) 0.0011(8) C24 0.0461(9) 0.0386(10) 0.0517(10) 0.0049(8) 0.0006(8) 0.0041(7) _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 C2 1.324(2) . ? O1 C1 1.446(3) . ? O2 C2 1.200(2) . ? O3 C13 1.215(3) . ? O4 C19 1.217(2) . ? N1 C5 1.380(2) . ? N1 C10 1.385(2) . ? N1 C6 1.446(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.536(3) . ? C3 C4 1.509(3) . ? C3 C14 1.517(2) . ? C3 C24 1.536(2) . ? C4 C5 1.353(3) . ? C4 C19 1.463(3) . ? C5 C17 1.503(3) . ? C6 C7 1.374(3) . ? C6 C16 1.381(3) . ? C7 C8 1.390(3) . ? C7 H7 0.9300 . ? C8 C9 1.360(4) . ? C8 H8 0.9300 . ? C9 C15 1.368(3) . ? C9 H9 0.9300 . ? C10 C14 1.344(3) . ? C10 C11 1.497(2) . ? C11 C12 1.533(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.515(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.462(3) . ? C15 C16 1.382(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C23 1.373(3) . ? C17 C18 1.406(3) . ? C18 C20 1.367(3) . ? C18 C19 1.489(3) . ? C20 C21 1.390(3) . ? C20 H20 0.9300 . ? C21 C22 1.375(3) . ? C21 H21 0.9300 . ? C22 C23 1.400(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 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 C2 O1 C1 116.30(18) . . ? C5 N1 C10 115.68(14) . . ? C5 N1 C6 124.10(15) . . ? C10 N1 C6 120.23(14) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 123.80(18) . . ? O2 C2 C3 122.68(19) . . ? O1 C2 C3 113.52(16) . . ? C4 C3 C14 105.45(15) . . ? C4 C3 C2 108.71(14) . . ? C14 C3 C2 108.57(14) . . ? C4 C3 C24 109.62(14) . . ? C14 C3 C24 110.69(14) . . ? C2 C3 C24 113.47(16) . . ? C5 C4 C19 108.78(16) . . ? C5 C4 C3 125.66(15) . . ? C19 C4 C3 125.40(16) . . ? C4 C5 N1 122.78(16) . . ? C4 C5 C17 110.85(14) . . ? N1 C5 C17 126.37(16) . . ? C7 C6 C16 120.22(17) . . ? C7 C6 N1 119.30(16) . . ? C16 C6 N1 120.45(15) . . ? C6 C7 C8 119.1(2) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C15 120.4(2) . . ? C8 C9 H9 119.8 . . ? C15 C9 H9 119.8 . . ? C14 C10 N1 124.23(15) . . ? C14 C10 C11 113.91(16) . . ? N1 C10 C11 121.86(16) . . ? C10 C11 C12 103.16(15) . . ? C10 C11 H11A 111.1 . . ? C12 C11 H11A 111.1 . . ? C10 C11 H11B 111.1 . . ? C12 C11 H11B 111.1 . . ? H11A C11 H11B 109.1 . . ? C13 C12 C11 105.88(15) . . ? C13 C12 H12A 110.6 . . ? C11 C12 H12A 110.6 . . ? C13 C12 H12B 110.6 . . ? C11 C12 H12B 110.6 . . ? H12A C12 H12B 108.7 . . ? O3 C13 C14 126.58(18) . . ? O3 C13 C12 125.60(18) . . ? C14 C13 C12 107.82(17) . . ? C10 C14 C13 109.22(16) . . ? C10 C14 C3 124.45(16) . . ? C13 C14 C3 126.22(17) . . ? C9 C15 C16 119.8(2) . . ? C9 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C6 C16 C15 119.83(18) . . ? C6 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C23 C17 C18 120.13(17) . . ? C23 C17 C5 134.64(17) . . ? C18 C17 C5 105.22(16) . . ? C20 C18 C17 121.35(19) . . ? C20 C18 C19 129.45(18) . . ? C17 C18 C19 109.20(15) . . ? O4 C19 C4 127.15(19) . . ? O4 C19 C18 126.96(18) . . ? C4 C19 C18 105.88(15) . . ? C18 C20 C21 118.41(19) . . ? C18 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C22 C21 C20 120.79(19) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 120.9(2) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C17 C23 C22 118.38(18) . . ? C17 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? C3 C24 H24A 109.5 . . ? C3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.121 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.037 data_a2 _database_code_depnum_ccdc_archive 'CCDC 905875' #TrackingRef 'cif-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H33 N O6' _chemical_formula_weight 527.59 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 ? _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 13.2463(15) _cell_length_b 10.6252(13) _cell_length_c 21.094(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.473(5) _cell_angle_gamma 90.00 _cell_volume 2887.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9802 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17581 _diffrn_reflns_av_R_equivalents 0.0964 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 24.88 _reflns_number_total 4742 _reflns_number_gt 2532 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0863P)^2^+1.4865P] 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 0.0058(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4742 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.2159 _refine_ls_wR_factor_gt 0.1789 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4520(3) -0.2175(3) 0.07275(17) 0.0964(11) Uani 1 1 d . . . O2 O 0.4853(5) -0.0196(4) 0.0754(2) 0.187(3) Uani 1 1 d . . . O3 O 0.6681(2) 0.1085(3) 0.26128(17) 0.0821(10) Uani 1 1 d . . . O4 O 0.3697(2) -0.2642(3) 0.24887(16) 0.0809(9) Uani 1 1 d . . . O5 O 0.4759(2) -0.0294(3) 0.33036(15) 0.0756(9) Uani 1 1 d . . . O6 O 0.5845(2) -0.1660(3) 0.30028(16) 0.0781(9) Uani 1 1 d . . . N1 N 0.3187(2) 0.1319(3) 0.14202(15) 0.0509(8) Uani 1 1 d . . . C1 C 0.2595(4) 0.2752(7) -0.0848(3) 0.130(2) Uani 1 1 d . . . H1A H 0.2150 0.3299 -0.1153 0.194 Uiso 1 1 calc R . . H1B H 0.2520 0.1905 -0.1009 0.194 Uiso 1 1 calc R . . H1C H 0.3303 0.3016 -0.0795 0.194 Uiso 1 1 calc R . . C2 C 0.2307(4) 0.2811(5) -0.0213(2) 0.0806(14) Uani 1 1 d . . . C3 C 0.2836(3) 0.2012(4) 0.0303(2) 0.0691(12) Uani 1 1 d . . . H3 H 0.3349 0.1462 0.0239 0.083 Uiso 1 1 calc R . . C4 C 0.2579(3) 0.2069(4) 0.0894(2) 0.0570(10) Uani 1 1 d . . . C5 C 0.2847(3) 0.0139(3) 0.15954(19) 0.0509(10) Uani 1 1 d . . . C6 C 0.3511(3) -0.0682(3) 0.19655(19) 0.0506(10) Uani 1 1 d . . . C7 C 0.4692(3) -0.0504(3) 0.2160(2) 0.0521(10) Uani 1 1 d . . . C8 C 0.5252(3) -0.1341(4) 0.1746(2) 0.0659(12) Uani 1 1 d . . . H8A H 0.5990 -0.1158 0.1865 0.079 Uiso 1 1 calc R . . H8B H 0.5161 -0.2218 0.1848 0.079 Uiso 1 1 calc R . . C9 C 0.4866(4) -0.1154(4) 0.1034(3) 0.0803(15) Uani 1 1 d . . . C10 C 0.4157(5) -0.2134(7) 0.0018(3) 0.118(2) Uani 1 1 d . . . H10A H 0.3524 -0.1643 -0.0104 0.141 Uiso 1 1 calc R . . H10B H 0.4678 -0.1749 -0.0175 0.141 Uiso 1 1 calc R . . C11 C 0.3965(6) -0.3429(7) -0.0210(3) 0.149(3) Uani 1 1 d . . . H11A H 0.4598 -0.3902 -0.0091 0.224 Uiso 1 1 calc R . . H11B H 0.3717 -0.3434 -0.0675 0.224 Uiso 1 1 calc R . . H11C H 0.3453 -0.3803 -0.0013 0.224 Uiso 1 1 calc R . . C12 C 0.4199(3) 0.1655(3) 0.17042(18) 0.0466(9) Uani 1 1 d . . . C13 C 0.4660(3) 0.2927(3) 0.16856(18) 0.0479(9) Uani 1 1 d . . . C14 C 0.5681(3) 0.2838(3) 0.20445(19) 0.0527(10) Uani 1 1 d . . . C15 C 0.5871(3) 0.1525(4) 0.2292(2) 0.0555(10) Uani 1 1 d . . . C16 C 0.4886(3) 0.0864(3) 0.20678(19) 0.0496(10) Uani 1 1 d . . . C17 C 0.6339(3) 0.3856(4) 0.2152(2) 0.0670(12) Uani 1 1 d . . . H17 H 0.7019 0.3781 0.2396 0.080 Uiso 1 1 calc R . . C18 C 0.5948(4) 0.5004(4) 0.1883(2) 0.0769(13) Uani 1 1 d . . . H18 H 0.6374 0.5711 0.1943 0.092 Uiso 1 1 calc R . . C19 C 0.4953(4) 0.5101(4) 0.1533(2) 0.0779(14) Uani 1 1 d . . . H19 H 0.4709 0.5879 0.1361 0.094 Uiso 1 1 calc R . . C20 C 0.4286(3) 0.4066(4) 0.1426(2) 0.0668(12) Uani 1 1 d . . . H20 H 0.3606 0.4146 0.1184 0.080 Uiso 1 1 calc R . . C21 C 0.1553(4) 0.3584(5) -0.0080(3) 0.0857(15) Uani 1 1 d . . . H21 H 0.1204 0.4112 -0.0411 0.103 Uiso 1 1 calc R . . C22 C 0.1283(4) 0.3633(5) 0.0496(3) 0.0855(14) Uani 1 1 d . . . H22 H 0.0757 0.4166 0.0557 0.103 Uiso 1 1 calc R . . C23 C 0.1808(3) 0.2869(4) 0.0996(2) 0.0678(12) Uani 1 1 d . . . H23 H 0.1643 0.2893 0.1401 0.081 Uiso 1 1 calc R . . C24 C 0.1701(3) -0.0091(4) 0.1378(2) 0.0644(11) Uani 1 1 d . . . H24A H 0.1463 0.0218 0.0935 0.077 Uiso 1 1 calc R . . H24B H 0.1353 0.0396 0.1652 0.077 Uiso 1 1 calc R . . C25 C 0.1376(3) -0.1471(4) 0.1397(2) 0.0679(12) Uani 1 1 d . . . C26 C 0.0214(3) -0.1534(5) 0.1345(3) 0.0987(17) Uani 1 1 d . . . H26A H 0.0008 -0.2395 0.1370 0.148 Uiso 1 1 calc R . . H26B H -0.0148 -0.1180 0.0936 0.148 Uiso 1 1 calc R . . H26C H 0.0047 -0.1065 0.1696 0.148 Uiso 1 1 calc R . . C27 C 0.1951(3) -0.2018(4) 0.2046(2) 0.0781(14) Uani 1 1 d . . . H27A H 0.1693 -0.1623 0.2392 0.094 Uiso 1 1 calc R . . H27B H 0.1799 -0.2911 0.2051 0.094 Uiso 1 1 calc R . . C28 C 0.3109(3) -0.1846(4) 0.2185(2) 0.0611(11) Uani 1 1 d . . . C29 C 0.1643(4) -0.2215(5) 0.0840(3) 0.0987(17) Uani 1 1 d . . . H29A H 0.1408 -0.3068 0.0852 0.148 Uiso 1 1 calc R . . H29B H 0.2381 -0.2209 0.0885 0.148 Uiso 1 1 calc R . . H29C H 0.1307 -0.1838 0.0431 0.148 Uiso 1 1 calc R . . C30 C 0.5082(3) -0.0803(4) 0.2880(2) 0.0614(11) Uani 1 1 d . . . C31 C 0.6201(5) -0.2095(6) 0.3668(3) 0.116(2) Uani 1 1 d . . . H31A H 0.6748 -0.1547 0.3902 0.139 Uiso 1 1 calc R . . H31B H 0.5633 -0.2074 0.3886 0.139 Uiso 1 1 calc R . . C32 C 0.6586(6) -0.3357(6) 0.3665(3) 0.150(3) Uani 1 1 d . . . H32A H 0.6048 -0.3890 0.3420 0.225 Uiso 1 1 calc R . . H32B H 0.6797 -0.3661 0.4104 0.225 Uiso 1 1 calc R . . H32C H 0.7169 -0.3366 0.3467 0.225 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 0.129(3) 0.086(2) 0.063(3) 0.0059(19) -0.001(2) -0.019(2) O2 0.420(9) 0.076(3) 0.097(3) 0.009(2) 0.125(5) 0.015(4) O3 0.0482(17) 0.078(2) 0.108(3) 0.0029(18) -0.0051(17) 0.0014(15) O4 0.086(2) 0.0621(18) 0.093(3) 0.0192(17) 0.0167(19) -0.0055(16) O5 0.084(2) 0.085(2) 0.057(2) -0.0012(16) 0.0149(17) 0.0045(16) O6 0.074(2) 0.081(2) 0.073(2) 0.0049(17) 0.0039(17) 0.0186(16) N1 0.0418(17) 0.0513(17) 0.054(2) 0.0035(16) 0.0010(15) -0.0085(14) C1 0.106(4) 0.204(7) 0.086(5) 0.028(4) 0.037(4) 0.005(4) C2 0.067(3) 0.115(4) 0.056(3) 0.008(3) 0.007(3) -0.029(3) C3 0.057(3) 0.083(3) 0.065(3) 0.003(3) 0.010(2) -0.017(2) C4 0.051(2) 0.062(2) 0.052(3) 0.006(2) -0.002(2) -0.018(2) C5 0.052(2) 0.049(2) 0.051(3) -0.0039(18) 0.0110(19) -0.0144(18) C6 0.048(2) 0.048(2) 0.053(3) -0.0012(19) 0.0077(19) -0.0055(17) C7 0.052(2) 0.048(2) 0.056(3) -0.0006(18) 0.012(2) 0.0006(17) C8 0.068(3) 0.056(2) 0.077(4) -0.004(2) 0.024(2) 0.007(2) C9 0.114(4) 0.057(3) 0.085(4) 0.014(3) 0.053(3) 0.019(3) C10 0.128(5) 0.152(6) 0.063(4) 0.017(4) 0.004(4) -0.022(4) C11 0.181(7) 0.160(7) 0.090(5) -0.034(5) -0.005(5) 0.023(6) C12 0.042(2) 0.048(2) 0.049(3) -0.0056(18) 0.0110(19) -0.0045(17) C13 0.048(2) 0.047(2) 0.046(3) -0.0047(18) 0.0071(19) -0.0073(17) C14 0.051(2) 0.055(2) 0.052(3) -0.0072(19) 0.012(2) -0.0052(18) C15 0.045(2) 0.063(2) 0.057(3) -0.006(2) 0.009(2) -0.0019(19) C16 0.047(2) 0.046(2) 0.055(3) -0.0064(18) 0.012(2) -0.0041(17) C17 0.054(2) 0.072(3) 0.072(3) -0.013(2) 0.009(2) -0.018(2) C18 0.083(3) 0.061(3) 0.082(4) -0.005(2) 0.010(3) -0.032(2) C19 0.082(3) 0.054(2) 0.087(4) 0.001(2) -0.003(3) -0.018(2) C20 0.055(2) 0.059(2) 0.079(3) 0.004(2) 0.001(2) -0.010(2) C21 0.064(3) 0.099(4) 0.088(4) 0.015(3) 0.005(3) -0.005(3) C22 0.073(3) 0.087(3) 0.093(4) 0.011(3) 0.011(3) 0.007(3) C23 0.059(3) 0.070(3) 0.068(3) 0.005(2) 0.002(2) -0.002(2) C24 0.047(2) 0.069(3) 0.073(3) 0.002(2) 0.005(2) -0.0186(19) C25 0.059(3) 0.072(3) 0.073(3) -0.007(2) 0.016(2) -0.027(2) C26 0.064(3) 0.100(4) 0.132(5) 0.008(3) 0.021(3) -0.035(3) C27 0.084(3) 0.070(3) 0.084(4) 0.005(3) 0.027(3) -0.024(2) C28 0.065(3) 0.058(2) 0.061(3) 0.000(2) 0.016(2) -0.012(2) C29 0.102(4) 0.096(4) 0.096(4) -0.028(3) 0.021(3) -0.030(3) C30 0.060(3) 0.060(2) 0.062(3) 0.001(2) 0.009(2) -0.003(2) C31 0.119(5) 0.140(5) 0.067(4) 0.011(4) -0.020(3) 0.051(4) C32 0.202(7) 0.098(5) 0.125(6) 0.038(4) -0.012(5) 0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.291(5) . ? O1 C10 1.462(6) . ? O2 C9 1.175(5) . ? O3 C15 1.221(4) . ? O4 C28 1.225(5) . ? O5 C30 1.204(5) . ? O6 C30 1.341(5) . ? O6 C31 1.447(6) . ? N1 C12 1.381(4) . ? N1 C5 1.411(4) . ? N1 C4 1.449(5) . ? C1 C2 1.477(7) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C21 1.372(7) . ? C2 C3 1.430(6) . ? C3 C4 1.367(6) . ? C3 H3 0.9300 . ? C4 C23 1.383(6) . ? C5 C6 1.351(5) . ? C5 C24 1.499(5) . ? C6 C28 1.464(5) . ? C6 C7 1.534(5) . ? C7 C16 1.496(5) . ? C7 C30 1.519(6) . ? C7 C8 1.552(5) . ? C8 C9 1.483(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C11 1.460(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C16 1.341(5) . ? C12 C13 1.488(5) . ? C13 C20 1.373(5) . ? C13 C14 1.390(5) . ? C14 C17 1.375(5) . ? C14 C15 1.490(5) . ? C15 C16 1.460(5) . ? C17 C18 1.394(6) . ? C17 H17 0.9300 . ? C18 C19 1.355(6) . ? C18 H18 0.9300 . ? C19 C20 1.396(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.346(7) . ? C21 H21 0.9300 . ? C22 C23 1.383(6) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.532(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C27 1.519(6) . ? C25 C26 1.520(5) . ? C25 C29 1.524(6) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.504(6) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C31 C32 1.435(7) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 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 C9 O1 C10 118.7(4) . . ? C30 O6 C31 117.7(4) . . ? C12 N1 C5 116.9(3) . . ? C12 N1 C4 120.0(3) . . ? C5 N1 C4 122.3(3) . . ? 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 . . ? C21 C2 C3 116.8(4) . . ? C21 C2 C1 124.4(5) . . ? C3 C2 C1 118.8(5) . . ? C4 C3 C2 119.1(4) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C23 121.2(4) . . ? C3 C4 N1 117.5(4) . . ? C23 C4 N1 121.2(4) . . ? C6 C5 N1 121.4(3) . . ? C6 C5 C24 123.3(3) . . ? N1 C5 C24 115.2(3) . . ? C5 C6 C28 119.5(3) . . ? C5 C6 C7 124.1(3) . . ? C28 C6 C7 116.3(3) . . ? C16 C7 C30 107.7(3) . . ? C16 C7 C6 106.3(3) . . ? C30 C7 C6 109.2(3) . . ? C16 C7 C8 111.4(3) . . ? C30 C7 C8 110.4(3) . . ? C6 C7 C8 111.7(3) . . ? C9 C8 C7 113.4(3) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? O2 C9 O1 121.0(5) . . ? O2 C9 C8 125.9(5) . . ? O1 C9 C8 113.1(4) . . ? C11 C10 O1 107.4(5) . . ? C11 C10 H10A 110.2 . . ? O1 C10 H10A 110.2 . . ? C11 C10 H10B 110.2 . . ? O1 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C16 C12 N1 123.2(3) . . ? C16 C12 C13 110.8(3) . . ? N1 C12 C13 125.9(3) . . ? C20 C13 C14 119.5(3) . . ? C20 C13 C12 134.4(3) . . ? C14 C13 C12 106.1(3) . . ? C17 C14 C13 122.4(4) . . ? C17 C14 C15 129.0(4) . . ? C13 C14 C15 108.6(3) . . ? O3 C15 C16 126.8(4) . . ? O3 C15 C14 127.4(3) . . ? C16 C15 C14 105.7(3) . . ? C12 C16 C15 108.7(3) . . ? C12 C16 C7 124.7(3) . . ? C15 C16 C7 126.3(3) . . ? C14 C17 C18 117.3(4) . . ? C14 C17 H17 121.3 . . ? C18 C17 H17 121.3 . . ? C19 C18 C17 120.7(4) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 121.8(4) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? C13 C20 C19 118.3(4) . . ? C13 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? C22 C21 C2 124.6(5) . . ? C22 C21 H21 117.7 . . ? C2 C21 H21 117.7 . . ? C21 C22 C23 118.3(5) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? C22 C23 C4 120.1(5) . . ? C22 C23 H23 120.0 . . ? C4 C23 H23 120.0 . . ? C5 C24 C25 114.7(3) . . ? C5 C24 H24A 108.6 . . ? C25 C24 H24A 108.6 . . ? C5 C24 H24B 108.6 . . ? C25 C24 H24B 108.6 . . ? H24A C24 H24B 107.6 . . ? C27 C25 C26 109.6(4) . . ? C27 C25 C29 109.8(4) . . ? C26 C25 C29 109.6(4) . . ? C27 C25 C24 107.8(3) . . ? C26 C25 C24 109.0(4) . . ? C29 C25 C24 111.1(4) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C25 113.8(3) . . ? C28 C27 H27A 108.8 . . ? C25 C27 H27A 108.8 . . ? C28 C27 H27B 108.8 . . ? C25 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? O4 C28 C6 121.0(4) . . ? O4 C28 C27 120.9(4) . . ? C6 C28 C27 118.1(4) . . ? C25 C29 H29A 109.5 . . ? C25 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O5 C30 O6 123.0(4) . . ? O5 C30 C7 123.4(4) . . ? O6 C30 C7 113.6(4) . . ? C32 C31 O6 109.3(5) . . ? C32 C31 H31A 109.8 . . ? O6 C31 H31A 109.8 . . ? C32 C31 H31B 109.8 . . ? O6 C31 H31B 109.8 . . ? H31A C31 H31B 108.3 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 24.88 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.273 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.049 data_a3 _database_code_depnum_ccdc_archive 'CCDC 905876' #TrackingRef 'cif-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H25 N O6' _chemical_formula_weight 507.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 15.366(2) _cell_length_b 10.1563(14) _cell_length_c 18.420(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.313(2) _cell_angle_gamma 90.00 _cell_volume 2744.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9798 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18803 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 25.38 _reflns_number_total 4982 _reflns_number_gt 2957 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1184P)^2^+0.5553P] 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 0.0023(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4982 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.2192 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.07911(17) 0.3321(3) -0.07118(13) 0.0869(7) Uani 1 1 d . . . O2 O 0.1100(2) 0.4299(3) 0.04085(14) 0.1068(9) Uani 1 1 d . . . O3 O 0.20892(15) 0.4910(2) -0.19977(11) 0.0765(7) Uani 1 1 d . . . O4 O 0.15397(19) 0.8244(3) 0.05045(14) 0.0985(8) Uani 1 1 d . . . O5 O 0.14021(19) 0.7862(3) -0.13567(14) 0.0962(8) Uani 1 1 d . . . O6 O 0.28934(16) 0.7861(2) -0.07524(13) 0.0788(7) Uani 1 1 d . . . N1 N 0.36085(15) 0.4731(2) 0.06509(11) 0.0551(6) Uani 1 1 d . . . C1 C 0.4321(4) 0.1829(4) 0.1911(3) 0.1065(14) Uani 1 1 d . . . C2 C 0.3779(3) 0.2728(3) 0.1390(2) 0.0771(9) Uani 1 1 d . . . H2 H 0.3158 0.2579 0.1179 0.093 Uiso 1 1 calc R . . C3 C 0.4175(2) 0.3819(3) 0.11953(15) 0.0592(8) Uani 1 1 d . . . C4 C 0.31308(19) 0.5729(3) 0.08666(14) 0.0532(7) Uani 1 1 d . . . C5 C 0.24458(19) 0.6387(3) 0.03706(15) 0.0546(7) Uani 1 1 d . . . C6 C 0.20551(18) 0.6096(3) -0.04661(14) 0.0539(7) Uani 1 1 d . . . C7 C 0.1055(2) 0.5583(3) -0.06769(16) 0.0673(8) Uani 1 1 d . . . H7A H 0.0671 0.6251 -0.0552 0.081 Uiso 1 1 calc R . . H7B H 0.0832 0.5423 -0.1220 0.081 Uiso 1 1 calc R . . C8 C 0.0993(2) 0.4357(4) -0.02653(18) 0.0699(9) Uani 1 1 d . . . C9 C 0.0727(3) 0.2057(4) -0.0346(2) 0.1018(12) Uani 1 1 d . . . H9A H 0.0313 0.2133 -0.0041 0.122 Uiso 1 1 calc R . . H9B H 0.1322 0.1805 -0.0015 0.122 Uiso 1 1 calc R . . C10 C 0.0392(4) 0.1051(5) -0.0940(3) 0.1294(17) Uani 1 1 d . . . H10A H -0.0218 0.1268 -0.1238 0.194 Uiso 1 1 calc R . . H10B H 0.0393 0.0206 -0.0706 0.194 Uiso 1 1 calc R . . H10C H 0.0781 0.1024 -0.1261 0.194 Uiso 1 1 calc R . . C11 C 0.2123(2) 0.7425(3) 0.07789(18) 0.0689(8) Uani 1 1 d . . . C12 C 0.2688(2) 0.7304(3) 0.15911(17) 0.0681(8) Uani 1 1 d . . . C13 C 0.2667(3) 0.8056(4) 0.2207(2) 0.0900(11) Uani 1 1 d . . . H13 H 0.2242 0.8728 0.2160 0.108 Uiso 1 1 calc R . . C14 C 0.3302(3) 0.7775(4) 0.2901(2) 0.0977(13) Uani 1 1 d . . . H14 H 0.3311 0.8276 0.3326 0.117 Uiso 1 1 calc R . . C15 C 0.3906(3) 0.6786(4) 0.29679(19) 0.0920(11) Uani 1 1 d . . . H15 H 0.4323 0.6617 0.3440 0.110 Uiso 1 1 calc R . . C16 C 0.3922(2) 0.6005(4) 0.23431(16) 0.0775(9) Uani 1 1 d . . . H16 H 0.4339 0.5321 0.2397 0.093 Uiso 1 1 calc R . . C17 C 0.33068(19) 0.6279(3) 0.16529(14) 0.0586(7) Uani 1 1 d . . . C18 C 0.33733(18) 0.4470(3) -0.01165(14) 0.0508(7) Uani 1 1 d . . . C19 C 0.3841(2) 0.3527(3) -0.04995(15) 0.0585(7) Uani 1 1 d . . . C20 C 0.3359(2) 0.3575(3) -0.12760(15) 0.0597(7) Uani 1 1 d . . . C21 C 0.3625(3) 0.2838(4) -0.18001(19) 0.0813(10) Uani 1 1 d . . . H21 H 0.3292 0.2861 -0.2312 0.098 Uiso 1 1 calc R . . C22 C 0.4397(3) 0.2066(4) -0.1551(2) 0.0991(13) Uani 1 1 d . . . H22 H 0.4586 0.1557 -0.1896 0.119 Uiso 1 1 calc R . . C23 C 0.4883(3) 0.2050(4) -0.0799(2) 0.1014(13) Uani 1 1 d . . . H23 H 0.5405 0.1534 -0.0642 0.122 Uiso 1 1 calc R . . C24 C 0.4620(2) 0.2783(4) -0.0258(2) 0.0826(10) Uani 1 1 d . . . H24 H 0.4964 0.2768 0.0252 0.099 Uiso 1 1 calc R . . C25 C 0.26232(19) 0.4573(3) -0.13905(15) 0.0569(7) Uani 1 1 d . . . C26 C 0.26789(17) 0.5087(3) -0.06386(13) 0.0495(7) Uani 1 1 d . . . C27 C 0.5224(4) 0.2054(6) 0.2200(2) 0.1180(18) Uani 1 1 d . . . H27 H 0.5586 0.1447 0.2535 0.142 Uiso 1 1 calc R . . C28 C 0.5607(3) 0.3137(6) 0.2014(2) 0.1057(14) Uani 1 1 d . . . H28 H 0.6228 0.3282 0.2229 0.127 Uiso 1 1 calc R . . C29 C 0.5085(2) 0.4049(4) 0.15017(18) 0.0800(10) Uani 1 1 d . . . H29 H 0.5352 0.4799 0.1372 0.096 Uiso 1 1 calc R . . C30 C 0.2054(2) 0.7375(3) -0.09205(17) 0.0654(8) Uani 1 1 d . . . C31 C 0.2984(3) 0.9175(4) -0.1045(2) 0.1050(13) Uani 1 1 d . . . H31A H 0.3571 0.9254 -0.1138 0.126 Uiso 1 1 calc R . . H31B H 0.2512 0.9309 -0.1524 0.126 Uiso 1 1 calc R . . C32 C 0.2906(3) 1.0167(4) -0.0501(3) 0.1285(17) Uani 1 1 d . . . H32A H 0.2324 1.0089 -0.0412 0.193 Uiso 1 1 calc R . . H32B H 0.2962 1.1027 -0.0699 0.193 Uiso 1 1 calc R . . H32C H 0.3382 1.0042 -0.0032 0.193 Uiso 1 1 calc R . . C50 C 0.3959(5) 0.0702(6) 0.2183(4) 0.199(3) Uani 1 1 d . . . H50A H 0.4145 0.0714 0.2729 0.298 Uiso 1 1 calc R . . H50B H 0.4184 -0.0083 0.2011 0.298 Uiso 1 1 calc R . . H50C H 0.3306 0.0717 0.1994 0.298 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 0.1084(18) 0.0868(17) 0.0703(15) -0.0044(13) 0.0342(13) -0.0090(14) O2 0.140(2) 0.119(2) 0.0605(16) 0.0051(14) 0.0283(14) -0.0411(18) O3 0.0852(14) 0.0989(17) 0.0376(11) -0.0037(11) 0.0064(10) 0.0066(13) O4 0.1049(18) 0.109(2) 0.0783(16) -0.0088(14) 0.0222(14) 0.0438(16) O5 0.1076(19) 0.0951(18) 0.0747(16) 0.0286(14) 0.0101(14) 0.0209(15) O6 0.0965(17) 0.0605(14) 0.0835(16) 0.0081(11) 0.0332(13) -0.0071(12) N1 0.0678(14) 0.0603(14) 0.0333(12) 0.0002(10) 0.0091(10) 0.0091(11) C1 0.153(4) 0.078(3) 0.107(3) 0.039(2) 0.068(3) 0.037(3) C2 0.093(2) 0.067(2) 0.079(2) 0.0091(18) 0.0361(19) 0.0123(18) C3 0.0741(19) 0.0642(19) 0.0385(15) 0.0012(13) 0.0156(13) 0.0122(15) C4 0.0635(16) 0.0591(17) 0.0383(14) -0.0024(12) 0.0170(12) -0.0008(14) C5 0.0626(16) 0.0620(17) 0.0410(15) -0.0021(13) 0.0181(13) 0.0015(14) C6 0.0591(16) 0.0614(17) 0.0401(14) 0.0006(13) 0.0130(12) 0.0039(13) C7 0.0617(17) 0.089(2) 0.0491(16) 0.0016(16) 0.0127(13) 0.0010(16) C8 0.0660(19) 0.094(3) 0.0490(18) -0.0014(18) 0.0166(14) -0.0105(17) C9 0.125(3) 0.087(3) 0.102(3) 0.000(2) 0.047(3) -0.009(2) C10 0.160(5) 0.093(3) 0.141(4) -0.020(3) 0.054(4) -0.004(3) C11 0.074(2) 0.078(2) 0.0569(19) -0.0069(16) 0.0231(15) 0.0108(18) C12 0.0744(19) 0.082(2) 0.0519(18) -0.0116(15) 0.0251(15) -0.0016(17) C13 0.103(3) 0.105(3) 0.065(2) -0.029(2) 0.031(2) 0.008(2) C14 0.120(3) 0.121(3) 0.057(2) -0.032(2) 0.034(2) -0.007(3) C15 0.107(3) 0.120(3) 0.0456(19) -0.015(2) 0.0174(18) 0.000(3) C16 0.088(2) 0.096(2) 0.0424(17) -0.0123(16) 0.0115(15) 0.0032(19) C17 0.0674(17) 0.0701(19) 0.0407(16) -0.0066(13) 0.0196(13) -0.0054(15) C18 0.0616(16) 0.0530(16) 0.0372(14) -0.0026(12) 0.0139(12) -0.0025(13) C19 0.0712(18) 0.0565(17) 0.0488(16) -0.0043(13) 0.0193(14) 0.0013(14) C20 0.0743(18) 0.0603(17) 0.0456(16) -0.0090(13) 0.0196(14) -0.0044(15) C21 0.102(3) 0.090(2) 0.0539(19) -0.0183(17) 0.0253(18) 0.008(2) C22 0.121(3) 0.104(3) 0.077(3) -0.024(2) 0.037(2) 0.027(3) C23 0.110(3) 0.114(3) 0.082(3) -0.010(2) 0.030(2) 0.048(2) C24 0.089(2) 0.092(3) 0.062(2) -0.0073(18) 0.0152(17) 0.028(2) C25 0.0659(17) 0.0625(18) 0.0420(15) -0.0015(13) 0.0155(13) -0.0049(14) C26 0.0562(15) 0.0557(16) 0.0364(14) -0.0019(12) 0.0136(11) -0.0045(12) C27 0.138(5) 0.139(5) 0.078(3) 0.032(3) 0.034(3) 0.073(4) C28 0.084(3) 0.147(4) 0.069(2) -0.003(3) -0.004(2) 0.040(3) C29 0.071(2) 0.102(3) 0.0571(19) 0.0015(18) 0.0039(16) 0.0057(19) C30 0.085(2) 0.065(2) 0.0473(17) 0.0040(15) 0.0222(16) 0.0122(18) C31 0.152(4) 0.067(2) 0.106(3) 0.014(2) 0.054(3) -0.011(2) C32 0.152(4) 0.071(3) 0.160(5) -0.004(3) 0.042(4) -0.006(3) C50 0.242(8) 0.127(5) 0.260(8) 0.089(5) 0.125(7) 0.037(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.314(4) . ? O1 C9 1.467(5) . ? O2 C8 1.204(4) . ? O3 C25 1.223(3) . ? O4 C11 1.217(4) . ? O5 C30 1.189(4) . ? O6 C30 1.329(4) . ? O6 C31 1.461(4) . ? N1 C18 1.376(3) . ? N1 C4 1.378(3) . ? N1 C3 1.449(3) . ? C1 C27 1.350(7) . ? C1 C2 1.404(5) . ? C1 C50 1.427(7) . ? C2 C3 1.363(4) . ? C2 H2 0.9300 . ? C3 C29 1.363(4) . ? C4 C5 1.348(4) . ? C4 C17 1.500(4) . ? C5 C11 1.465(4) . ? C5 C6 1.508(4) . ? C6 C26 1.500(4) . ? C6 C30 1.545(4) . ? C6 C7 1.559(4) . ? C7 C8 1.476(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C10 1.472(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.495(4) . ? C12 C13 1.376(4) . ? C12 C17 1.392(4) . ? C13 C14 1.387(5) . ? C13 H13 0.9300 . ? C14 C15 1.348(5) . ? C14 H14 0.9300 . ? C15 C16 1.404(5) . ? C15 H15 0.9300 . ? C16 C17 1.368(4) . ? C16 H16 0.9300 . ? C18 C26 1.358(4) . ? C18 C19 1.495(4) . ? C19 C24 1.373(4) . ? C19 C20 1.402(4) . ? C20 C21 1.376(4) . ? C20 C25 1.486(4) . ? C21 C22 1.382(5) . ? C21 H21 0.9300 . ? C22 C23 1.364(5) . ? C22 H22 0.9300 . ? C23 C24 1.396(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.458(4) . ? C27 C28 1.339(7) . ? C27 H27 0.9300 . ? C28 C29 1.394(5) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C31 C32 1.452(6) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 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 C8 O1 C9 116.7(3) . . ? C30 O6 C31 116.4(3) . . ? C18 N1 C4 116.0(2) . . ? C18 N1 C3 120.5(2) . . ? C4 N1 C3 122.2(2) . . ? C27 C1 C2 119.4(4) . . ? C27 C1 C50 117.3(5) . . ? C2 C1 C50 123.3(6) . . ? C3 C2 C1 119.2(4) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C29 120.9(3) . . ? C2 C3 N1 118.6(3) . . ? C29 C3 N1 120.5(3) . . ? C5 C4 N1 123.0(2) . . ? C5 C4 C17 110.5(2) . . ? N1 C4 C17 126.4(2) . . ? C4 C5 C11 108.9(2) . . ? C4 C5 C6 126.1(2) . . ? C11 C5 C6 125.0(3) . . ? C26 C6 C5 105.4(2) . . ? C26 C6 C30 110.9(2) . . ? C5 C6 C30 108.9(2) . . ? C26 C6 C7 111.4(2) . . ? C5 C6 C7 112.6(2) . . ? C30 C6 C7 107.7(2) . . ? C8 C7 C6 111.3(2) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O2 C8 O1 122.7(3) . . ? O2 C8 C7 124.1(3) . . ? O1 C8 C7 113.2(3) . . ? O1 C9 C10 108.8(4) . . ? O1 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? O1 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 C5 126.8(3) . . ? O4 C11 C12 127.5(3) . . ? C5 C11 C12 105.7(3) . . ? C13 C12 C17 122.1(3) . . ? C13 C12 C11 129.1(3) . . ? C17 C12 C11 108.8(3) . . ? C12 C13 C14 117.6(4) . . ? C12 C13 H13 121.2 . . ? C14 C13 H13 121.2 . . ? C15 C14 C13 120.9(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 121.7(3) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 118.1(3) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C16 C17 C12 119.6(3) . . ? C16 C17 C4 134.2(3) . . ? C12 C17 C4 106.1(2) . . ? C26 C18 N1 123.3(2) . . ? C26 C18 C19 110.4(2) . . ? N1 C18 C19 126.3(2) . . ? C24 C19 C20 119.7(3) . . ? C24 C19 C18 134.0(3) . . ? C20 C19 C18 106.1(2) . . ? C21 C20 C19 121.3(3) . . ? C21 C20 C25 130.1(3) . . ? C19 C20 C25 108.5(2) . . ? C20 C21 C22 118.8(3) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C23 C22 C21 119.9(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 122.2(4) . . ? C22 C23 H23 118.9 . . ? C24 C23 H23 118.9 . . ? C19 C24 C23 118.1(3) . . ? C19 C24 H24 121.0 . . ? C23 C24 H24 121.0 . . ? O3 C25 C26 127.1(3) . . ? O3 C25 C20 126.5(3) . . ? C26 C25 C20 106.4(2) . . ? C18 C26 C25 108.6(2) . . ? C18 C26 C6 125.6(2) . . ? C25 C26 C6 125.8(2) . . ? C28 C27 C1 121.1(4) . . ? C28 C27 H27 119.5 . . ? C1 C27 H27 119.5 . . ? C27 C28 C29 120.7(4) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C3 C29 C28 118.6(4) . . ? C3 C29 H29 120.7 . . ? C28 C29 H29 120.7 . . ? O5 C30 O6 124.5(3) . . ? O5 C30 C6 125.5(3) . . ? O6 C30 C6 110.0(3) . . ? C32 C31 O6 110.0(3) . . ? C32 C31 H31A 109.7 . . ? O6 C31 H31A 109.7 . . ? C32 C31 H31B 109.7 . . ? O6 C31 H31B 109.7 . . ? H31A C31 H31B 108.2 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C1 C50 H50A 109.5 . . ? C1 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C1 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.755 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.044 data_a4 _database_code_depnum_ccdc_archive 'CCDC 905877' #TrackingRef 'cif-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H21 N O4' _chemical_formula_weight 447.47 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 ? _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 8.4764(13) _cell_length_b 26.185(4) _cell_length_c 10.0293(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.002(4) _cell_angle_gamma 90.00 _cell_volume 2223.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9804 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7607 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 21.35 _reflns_number_total 2484 _reflns_number_gt 1856 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+1.8004P] 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 0.0049(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2484 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1302 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.6851(5) 0.81376(13) 1.0686(3) 0.0946(12) Uani 1 1 d . . . O2 O 0.8377(5) 0.75848(13) 0.9609(4) 0.1301(17) Uani 1 1 d . . . O3 O 1.0955(4) 0.79181(11) 1.2002(3) 0.0885(11) Uani 1 1 d . . . O4 O 0.8592(3) 1.03351(9) 1.1795(2) 0.0578(7) Uani 1 1 d . . . C1 C 0.6468(7) 0.84866(18) 0.5120(5) 0.0800(14) Uani 1 1 d . . . H1 H 0.6100 0.8408 0.4254 0.096 Uiso 1 1 calc R . . C2 C 0.5721(6) 0.82933(16) 0.6179(5) 0.0753(14) Uani 1 1 d . . . H2 H 0.4869 0.8073 0.6036 0.090 Uiso 1 1 calc R . . C3 C 0.6225(5) 0.84238(14) 0.7464(4) 0.0586(11) Uani 1 1 d . . . H3 H 0.5693 0.8303 0.8188 0.070 Uiso 1 1 calc R . . C4 C 0.7523(4) 0.87356(14) 0.7664(3) 0.0470(10) Uani 1 1 d . . . N1 N 0.8105(3) 0.88688(11) 0.9002(3) 0.0460(8) Uani 1 1 d . . . C6 C 0.9099(5) 0.84675(13) 0.9712(4) 0.0549(11) Uani 1 1 d . . . C7 C 0.9759(4) 0.86736(14) 1.1018(3) 0.0478(10) Uani 1 1 d . . . C8 C 1.0673(5) 0.83764(15) 1.2015(4) 0.0561(11) Uani 1 1 d . . . C9 C 1.1162(4) 0.87412(14) 1.3100(4) 0.0483(10) Uani 1 1 d . . . C10 C 1.2054(5) 0.86675(16) 1.4258(4) 0.0602(11) Uani 1 1 d . . . H10 H 1.2466 0.8347 1.4477 0.072 Uiso 1 1 calc R . . C11 C 1.2328(5) 0.90818(16) 1.5100(4) 0.0602(11) Uani 1 1 d . . . H11 H 1.2916 0.9039 1.5902 0.072 Uiso 1 1 calc R . . C12 C 1.1742(4) 0.95511(15) 1.4761(4) 0.0553(10) Uani 1 1 d . . . H12 H 1.1956 0.9826 1.5330 0.066 Uiso 1 1 calc R . . C13 C 1.0530(4) 0.92199(13) 1.2754(3) 0.0424(9) Uani 1 1 d . . . C14 C 0.9614(4) 0.91639(13) 1.1450(3) 0.0418(9) Uani 1 1 d . . . C15 C 0.8675(4) 0.95134(12) 1.0679(3) 0.0403(9) Uani 1 1 d . . . C16 C 0.8214(4) 1.00423(14) 1.0880(3) 0.0436(9) Uani 1 1 d . . . C17 C 0.7123(4) 1.01758(13) 0.9711(3) 0.0415(9) Uani 1 1 d . . . C18 C 0.6336(4) 1.06248(14) 0.9450(4) 0.0529(10) Uani 1 1 d . . . H18 H 0.6470 1.0903 1.0021 0.064 Uiso 1 1 calc R . . C19 C 0.5333(5) 1.06543(15) 0.8310(4) 0.0585(11) Uani 1 1 d . . . H19 H 0.4790 1.0956 0.8111 0.070 Uiso 1 1 calc R . . C20 C 0.5140(4) 1.02419(16) 0.7480(4) 0.0578(11) Uani 1 1 d . . . H20 H 0.4460 1.0268 0.6725 0.069 Uiso 1 1 calc R . . C21 C 0.5937(4) 0.97850(14) 0.7735(4) 0.0519(10) Uani 1 1 d . . . H21 H 0.5798 0.9507 0.7164 0.062 Uiso 1 1 calc R . . C22 C 0.6942(4) 0.97567(13) 0.8863(3) 0.0408(9) Uani 1 1 d . . . C23 C 0.7937(4) 0.93415(13) 0.9486(3) 0.0419(9) Uani 1 1 d . . . C24 C 0.8072(7) 0.80134(18) 0.9975(6) 0.0845(16) Uani 1 1 d . . . C25 C 0.5779(11) 0.7734(3) 1.1117(9) 0.190(4) Uani 1 1 d . . . H25A H 0.6315 0.7411 1.1010 0.228 Uiso 1 1 calc R . . H25B H 0.5664 0.7780 1.2067 0.228 Uiso 1 1 calc R . . C26 C 1.0455(6) 0.83114(19) 0.8831(4) 0.0891(16) Uani 1 1 d . . . H26A H 1.0025 0.8158 0.8022 0.134 Uiso 1 1 calc R . . H26B H 1.1129 0.8070 0.9305 0.134 Uiso 1 1 calc R . . H26C H 1.1057 0.8608 0.8618 0.134 Uiso 1 1 calc R . . C27 C 0.7769(6) 0.87980(19) 0.5330(4) 0.0779(13) Uani 1 1 d . . . H27 H 0.8284 0.8926 0.4605 0.093 Uiso 1 1 calc R . . C28 C 0.8304(5) 0.89186(15) 0.6602(4) 0.0591(11) Uani 1 1 d . . . H28 H 0.9193 0.9124 0.6744 0.071 Uiso 1 1 calc R . . C29 C 1.0827(4) 0.96302(14) 1.3579(3) 0.0496(10) Uani 1 1 d . . . H29 H 1.0430 0.9952 1.3358 0.060 Uiso 1 1 calc R . . C30 C 0.4446(8) 0.7689(4) 1.0593(12) 0.241(6) Uani 1 1 d . . . H30A H 0.3899 0.7420 1.1024 0.361 Uiso 1 1 calc R . . H30B H 0.4517 0.7610 0.9664 0.361 Uiso 1 1 calc R . . H30C H 0.3878 0.8004 1.0681 0.361 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 0.115(3) 0.071(2) 0.097(3) 0.0201(19) -0.002(2) -0.046(2) O2 0.125(3) 0.039(2) 0.215(4) -0.014(2) -0.087(3) 0.003(2) O3 0.119(3) 0.0462(19) 0.095(2) -0.0082(16) -0.036(2) 0.0171(18) O4 0.0714(18) 0.0465(16) 0.0546(16) -0.0107(14) -0.0048(14) 0.0056(14) C1 0.110(4) 0.070(3) 0.057(3) -0.012(3) -0.022(3) 0.013(3) C2 0.081(3) 0.053(3) 0.087(4) 0.003(3) -0.044(3) -0.011(2) C3 0.057(3) 0.051(3) 0.065(3) 0.010(2) -0.020(2) -0.014(2) C4 0.053(2) 0.041(2) 0.045(2) -0.0020(18) -0.0068(19) -0.0005(19) N1 0.0484(19) 0.042(2) 0.0471(19) -0.0056(15) -0.0062(14) -0.0008(15) C6 0.058(3) 0.035(2) 0.069(3) -0.0104(19) -0.018(2) 0.007(2) C7 0.045(2) 0.040(2) 0.057(2) -0.0064(19) -0.0108(18) 0.0000(18) C8 0.059(3) 0.044(3) 0.065(3) -0.003(2) -0.011(2) 0.006(2) C9 0.046(2) 0.047(2) 0.051(2) 0.0014(19) -0.0053(19) 0.0018(19) C10 0.062(3) 0.054(3) 0.063(3) 0.005(2) -0.011(2) 0.005(2) C11 0.064(3) 0.066(3) 0.049(2) 0.000(2) -0.014(2) 0.001(2) C12 0.059(3) 0.056(3) 0.050(2) -0.009(2) -0.003(2) -0.001(2) C13 0.041(2) 0.043(2) 0.044(2) -0.0012(18) 0.0030(17) -0.0041(18) C14 0.034(2) 0.044(2) 0.047(2) -0.0003(18) 0.0008(17) -0.0003(17) C15 0.038(2) 0.037(2) 0.046(2) -0.0030(17) -0.0006(17) 0.0015(17) C16 0.045(2) 0.045(2) 0.041(2) -0.0025(19) 0.0049(17) -0.0028(18) C17 0.039(2) 0.039(2) 0.046(2) 0.0009(18) 0.0059(17) -0.0007(17) C18 0.052(2) 0.043(2) 0.065(3) 0.0006(19) 0.007(2) 0.005(2) C19 0.055(3) 0.049(3) 0.071(3) 0.012(2) -0.001(2) 0.011(2) C20 0.051(2) 0.059(3) 0.062(3) 0.011(2) -0.008(2) 0.003(2) C21 0.050(2) 0.052(3) 0.054(2) 0.0027(19) 0.002(2) -0.002(2) C22 0.037(2) 0.041(2) 0.044(2) 0.0072(18) 0.0039(17) -0.0024(17) C23 0.043(2) 0.036(2) 0.047(2) -0.0008(18) 0.0047(17) -0.0048(18) C24 0.111(5) 0.042(3) 0.094(4) 0.008(3) -0.058(3) -0.007(3) C25 0.183(8) 0.145(6) 0.234(9) 0.108(6) -0.063(7) -0.119(7) C26 0.083(3) 0.104(4) 0.078(3) -0.036(3) -0.021(3) 0.045(3) C27 0.088(4) 0.090(4) 0.056(3) -0.001(3) 0.008(3) 0.005(3) C28 0.057(3) 0.063(3) 0.057(3) -0.004(2) 0.002(2) -0.006(2) C29 0.051(2) 0.048(2) 0.049(2) -0.001(2) 0.0011(19) 0.0021(19) C30 0.078(5) 0.234(10) 0.406(15) 0.204(11) -0.026(7) -0.042(6) _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 C24 1.328(6) . ? O1 C25 1.473(6) . ? O2 C24 1.213(6) . ? O3 C8 1.224(4) . ? O4 C16 1.226(4) . ? C1 C2 1.362(6) . ? C1 C27 1.379(6) . ? C1 H1 0.9300 . ? C2 C3 1.379(5) . ? C2 H2 0.9300 . ? C3 C4 1.376(5) . ? C3 H3 0.9300 . ? C4 C28 1.370(5) . ? C4 N1 1.448(4) . ? N1 C23 1.340(4) . ? N1 C6 1.503(4) . ? C6 C7 1.498(5) . ? C6 C24 1.505(6) . ? C6 C26 1.541(6) . ? C7 C14 1.363(5) . ? C7 C8 1.457(5) . ? C8 C9 1.490(5) . ? C9 C10 1.366(5) . ? C9 C13 1.400(5) . ? C10 C11 1.387(5) . ? C10 H10 0.9300 . ? C11 C12 1.362(5) . ? C11 H11 0.9300 . ? C12 C29 1.398(5) . ? C12 H12 0.9300 . ? C13 C29 1.371(5) . ? C13 C14 1.492(5) . ? C14 C15 1.416(5) . ? C15 C23 1.395(5) . ? C15 C16 1.456(5) . ? C16 C17 1.497(5) . ? C17 C18 1.370(5) . ? C17 C22 1.391(5) . ? C18 C19 1.391(5) . ? C18 H18 0.9300 . ? C19 C20 1.368(5) . ? C19 H19 0.9300 . ? C20 C21 1.391(5) . ? C20 H20 0.9300 . ? C21 C22 1.382(5) . ? C21 H21 0.9300 . ? C22 C23 1.493(5) . ? C25 C30 1.227(9) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.368(6) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 C24 O1 C25 119.5(6) . . ? C2 C1 C27 120.1(4) . . ? C2 C1 H1 120.0 . . ? C27 C1 H1 120.0 . . ? C1 C2 C3 120.2(4) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.3(4) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C28 C4 C3 120.6(4) . . ? C28 C4 N1 118.8(3) . . ? C3 C4 N1 120.6(3) . . ? C23 N1 C4 121.4(3) . . ? C23 N1 C6 122.8(3) . . ? C4 N1 C6 115.2(3) . . ? C7 C6 N1 109.7(3) . . ? C7 C6 C24 108.9(3) . . ? N1 C6 C24 108.7(3) . . ? C7 C6 C26 110.0(3) . . ? N1 C6 C26 109.3(3) . . ? C24 C6 C26 110.3(4) . . ? C14 C7 C8 109.8(3) . . ? C14 C7 C6 125.6(3) . . ? C8 C7 C6 124.6(3) . . ? O3 C8 C7 127.8(3) . . ? O3 C8 C9 126.1(3) . . ? C7 C8 C9 106.0(3) . . ? C10 C9 C13 121.7(3) . . ? C10 C9 C8 130.6(4) . . ? C13 C9 C8 107.7(3) . . ? C9 C10 C11 118.3(4) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C12 C11 C10 120.4(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C29 121.6(4) . . ? C11 C12 H12 119.2 . . ? C29 C12 H12 119.2 . . ? C29 C13 C9 119.7(3) . . ? C29 C13 C14 132.6(3) . . ? C9 C13 C14 107.7(3) . . ? C7 C14 C15 119.5(3) . . ? C7 C14 C13 108.6(3) . . ? C15 C14 C13 131.8(3) . . ? C23 C15 C14 118.3(3) . . ? C23 C15 C16 108.3(3) . . ? C14 C15 C16 133.3(3) . . ? O4 C16 C15 129.6(3) . . ? O4 C16 C17 124.6(3) . . ? C15 C16 C17 105.8(3) . . ? C18 C17 C22 121.6(3) . . ? C18 C17 C16 128.7(3) . . ? C22 C17 C16 109.7(3) . . ? C17 C18 C19 118.4(4) . . ? C17 C18 H18 120.8 . . ? C19 C18 H18 120.8 . . ? C20 C19 C18 120.3(4) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 121.7(4) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C22 C21 C20 118.0(4) . . ? C22 C21 H21 121.0 . . ? C20 C21 H21 121.0 . . ? C21 C22 C17 120.1(3) . . ? C21 C22 C23 133.8(3) . . ? C17 C22 C23 106.1(3) . . ? N1 C23 C15 123.9(3) . . ? N1 C23 C22 126.1(3) . . ? C15 C23 C22 110.0(3) . . ? O2 C24 O1 125.0(6) . . ? O2 C24 C6 122.9(6) . . ? O1 C24 C6 112.0(4) . . ? C30 C25 O1 120.8(7) . . ? C30 C25 H25A 107.1 . . ? O1 C25 H25A 107.1 . . ? C30 C25 H25B 107.1 . . ? O1 C25 H25B 107.1 . . ? H25A C25 H25B 106.8 . . ? C6 C26 H26A 109.5 . . ? C6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C1 120.2(4) . . ? C28 C27 H27 119.9 . . ? C1 C27 H27 119.9 . . ? C27 C28 C4 119.6(4) . . ? C27 C28 H28 120.2 . . ? C4 C28 H28 120.2 . . ? C13 C29 C12 118.2(3) . . ? C13 C29 H29 120.9 . . ? C12 C29 H29 120.9 . . ? C25 C30 H30A 109.5 . . ? C25 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C25 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 21.35 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.425 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.043