# Electronic Supplementary Material (ESI) for Chemical Science # 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_1 _database_code_depnum_ccdc_archive 'CCDC 892907' #TrackingRef '12725_web_deposit_cif_file_0_JinXie_1342766074.Xiejin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 N O4' _chemical_formula_sum 'C23 H25 N O4' _chemical_formula_weight 379.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.485(12) _cell_length_b 5.944(3) _cell_length_c 18.057(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.841(13) _cell_angle_gamma 90.00 _cell_volume 1982(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1304 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 22.81 _exptl_crystal_description rod-like _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9761 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details 'SADABS; Bruker, 2008' _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 'Bruker Smart Aepex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9500 _diffrn_reflns_av_R_equivalents 0.0964 _diffrn_reflns_av_sigmaI/netI 0.1049 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3353 _reflns_number_gt 1681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.5000P] 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 3353 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1235 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1862 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.29332(12) 0.6823(4) -0.05006(12) 0.0442(6) Uani 1 1 d . . . O4 O 0.24944(11) 1.0427(3) 0.06127(11) 0.0391(6) Uani 1 1 d . . . N1 N 0.24402(14) 0.8217(4) 0.09528(14) 0.0377(7) Uani 1 1 d . . . O2 O 0.27033(15) 0.9801(4) -0.12548(14) 0.0633(8) Uani 1 1 d . . . C4 C 0.30978(17) 0.7597(5) 0.13168(17) 0.0366(8) Uani 1 1 d . . . C16 C 0.17978(17) 1.0502(5) 0.02342(18) 0.0403(8) Uani 1 1 d . . . O3 O 0.13037(13) 0.7792(4) -0.06528(15) 0.0601(7) Uani 1 1 d . . . C19 C 0.25499(19) 0.8536(6) -0.07661(19) 0.0437(9) Uani 1 1 d . . . C9 C 0.13110(17) 1.1660(6) 0.19894(19) 0.0441(9) Uani 1 1 d . . . C15 C 0.12718(18) 0.9732(6) 0.08254(18) 0.0427(8) Uani 1 1 d . . . H15A H 0.0887 0.8763 0.0611 0.051 Uiso 1 1 calc R . . C3 C 0.37294(18) 0.8812(6) 0.12560(18) 0.0439(9) Uani 1 1 d . . . H3 H 0.3721 1.0173 0.1001 0.053 Uiso 1 1 calc R . . C17 C 0.1693(2) 1.2828(6) -0.0096(2) 0.0497(9) Uani 1 1 d . . . H17A H 0.1750 1.3936 0.0289 0.075 Uiso 1 1 calc R . . H17B H 0.1216 1.2942 -0.0329 0.075 Uiso 1 1 calc R . . H17C H 0.2048 1.3081 -0.0458 0.075 Uiso 1 1 calc R . . C7 C 0.17838(17) 0.8434(6) 0.13688(18) 0.0427(8) Uani 1 1 d . . . H7A H 0.1584 0.6946 0.1471 0.051 Uiso 1 1 calc R . . C14 C 0.09719(17) 1.1579(6) 0.1289(2) 0.0448(9) Uani 1 1 d . . . C20 C 0.36315(18) 0.6120(6) -0.07992(18) 0.0427(8) Uani 1 1 d . . . C18 C 0.18261(19) 0.8768(6) -0.03970(18) 0.0415(8) Uani 1 1 d . . . C8 C 0.1861(2) 0.9822(6) 0.20827(18) 0.0524(10) Uani 1 1 d . . . H8A H 0.1766 0.8901 0.2510 0.063 Uiso 1 1 calc R . . H8B H 0.2345 1.0444 0.2147 0.063 Uiso 1 1 calc R . . C5 C 0.3117(2) 0.5611(6) 0.1713(2) 0.0528(10) Uani 1 1 d . . . H5 H 0.2695 0.4791 0.1766 0.063 Uiso 1 1 calc R . . C10 C 0.1114(2) 1.3279(7) 0.2495(2) 0.0562(10) Uani 1 1 d . . . H10 H 0.1351 1.3363 0.2961 0.067 Uiso 1 1 calc R . . C21 C 0.3875(2) 0.4277(6) -0.0272(2) 0.0556(10) Uani 1 1 d . . . H21A H 0.3929 0.4872 0.0222 0.083 Uiso 1 1 calc R . . H21B H 0.4330 0.3687 -0.0416 0.083 Uiso 1 1 calc R . . H21C H 0.3520 0.3096 -0.0286 0.083 Uiso 1 1 calc R . . C22 C 0.4167(2) 0.8030(6) -0.0785(2) 0.0559(10) Uani 1 1 d . . . H22A H 0.4021 0.9116 -0.1156 0.084 Uiso 1 1 calc R . . H22B H 0.4638 0.7461 -0.0883 0.084 Uiso 1 1 calc R . . H22C H 0.4182 0.8731 -0.0305 0.084 Uiso 1 1 calc R . . C1 C 0.4385(2) 0.6032(7) 0.1957(2) 0.0580(11) Uani 1 1 d . . . H1 H 0.4820 0.5497 0.2170 0.070 Uiso 1 1 calc R . . C23 C 0.3476(2) 0.5216(6) -0.15837(19) 0.0562(10) Uani 1 1 d . . . H23A H 0.3105 0.4087 -0.1576 0.084 Uiso 1 1 calc R . . H23B H 0.3909 0.4567 -0.1764 0.084 Uiso 1 1 calc R . . H23C H 0.3316 0.6425 -0.1904 0.084 Uiso 1 1 calc R . . C12 C 0.0220(2) 1.4661(7) 0.1617(3) 0.0660(12) Uani 1 1 d . . . H12 H -0.0150 1.5681 0.1498 0.079 Uiso 1 1 calc R . . C2 C 0.4370(2) 0.8009(7) 0.1572(2) 0.0520(10) Uani 1 1 d . . . H2 H 0.4796 0.8819 0.1524 0.062 Uiso 1 1 calc R . . C6 C 0.3765(2) 0.4847(7) 0.2028(2) 0.0601(11) Uani 1 1 d . . . H6 H 0.3778 0.3505 0.2293 0.072 Uiso 1 1 calc R . . C11 C 0.0571(2) 1.4744(7) 0.2301(3) 0.0649(12) Uani 1 1 d . . . H11 H 0.0436 1.5823 0.2641 0.078 Uiso 1 1 calc R . . C13 C 0.04093(19) 1.3072(6) 0.1100(2) 0.0563(10) Uani 1 1 d . . . H13 H 0.0167 1.3001 0.0637 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 0.0512(14) 0.0389(15) 0.0436(14) 0.0043(10) 0.0125(11) 0.0067(11) O4 0.0445(13) 0.0352(14) 0.0375(13) 0.0052(10) 0.0019(10) -0.0056(10) N1 0.0413(15) 0.0363(17) 0.0358(15) 0.0097(12) 0.0052(12) -0.0050(12) O2 0.0831(19) 0.0528(18) 0.0560(17) 0.0207(13) 0.0223(15) 0.0097(14) C4 0.0430(19) 0.038(2) 0.0288(17) -0.0013(14) 0.0044(14) -0.0026(15) C16 0.0444(19) 0.036(2) 0.0402(19) 0.0027(15) 0.0021(16) -0.0025(15) O3 0.0493(15) 0.0682(19) 0.0621(18) -0.0160(13) -0.0054(13) -0.0042(13) C19 0.056(2) 0.037(2) 0.038(2) -0.0033(16) 0.0012(17) 0.0018(17) C9 0.0413(19) 0.048(2) 0.044(2) -0.0009(16) 0.0135(16) -0.0049(16) C15 0.0438(19) 0.043(2) 0.042(2) 0.0023(16) 0.0066(16) -0.0058(15) C3 0.050(2) 0.045(2) 0.0373(19) 0.0030(15) 0.0029(16) -0.0005(17) C17 0.059(2) 0.043(2) 0.048(2) 0.0055(17) 0.0078(18) 0.0066(17) C7 0.0461(19) 0.041(2) 0.042(2) 0.0050(15) 0.0117(16) -0.0015(15) C14 0.0365(18) 0.050(2) 0.049(2) 0.0002(17) 0.0119(16) -0.0047(16) C20 0.051(2) 0.043(2) 0.0353(19) -0.0044(15) 0.0089(16) 0.0005(16) C18 0.045(2) 0.040(2) 0.039(2) 0.0054(15) -0.0021(16) 0.0041(16) C8 0.061(2) 0.059(3) 0.038(2) 0.0035(17) 0.0092(18) -0.0002(19) C5 0.058(2) 0.048(2) 0.053(2) 0.0120(18) 0.0050(19) -0.0048(18) C10 0.059(2) 0.060(3) 0.050(2) -0.0049(19) 0.0177(19) -0.005(2) C21 0.064(2) 0.052(3) 0.051(2) 0.0018(18) 0.0045(19) 0.0110(19) C22 0.055(2) 0.055(3) 0.059(2) -0.0035(19) 0.0143(19) -0.0088(18) C1 0.051(2) 0.080(3) 0.043(2) 0.005(2) 0.0016(18) 0.014(2) C23 0.067(2) 0.060(3) 0.043(2) -0.0101(18) 0.0082(19) 0.0012(19) C12 0.056(2) 0.065(3) 0.079(3) 0.007(2) 0.026(2) 0.013(2) C2 0.051(2) 0.066(3) 0.039(2) 0.0022(19) 0.0016(17) -0.0050(19) C6 0.072(3) 0.059(3) 0.050(2) 0.0152(19) 0.004(2) 0.012(2) C11 0.070(3) 0.053(3) 0.075(3) -0.005(2) 0.035(2) 0.000(2) C13 0.045(2) 0.065(3) 0.060(3) 0.004(2) 0.0122(19) 0.0036(19) _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 C19 1.317(4) . ? O1 C20 1.483(4) . ? O4 C16 1.428(4) . ? O4 N1 1.456(3) . ? N1 C4 1.402(4) . ? N1 C7 1.464(4) . ? O2 C19 1.204(4) . ? C4 C5 1.380(5) . ? C4 C3 1.382(4) . ? C16 C17 1.514(4) . ? C16 C18 1.540(5) . ? C16 C15 1.548(4) . ? O3 C18 1.199(4) . ? C19 C18 1.530(5) . ? C9 C14 1.384(5) . ? C9 C10 1.387(5) . ? C9 C8 1.496(5) . ? C15 C14 1.503(5) . ? C15 C7 1.537(4) . ? C15 H15A 0.9800 . ? C3 C2 1.375(5) . ? C3 H3 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C7 C8 1.531(5) . ? C7 H7A 0.9800 . ? C14 C13 1.397(5) . ? C20 C21 1.505(5) . ? C20 C22 1.506(5) . ? C20 C23 1.529(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C5 C6 1.378(5) . ? C5 H5 0.9300 . ? C10 C11 1.362(5) . ? C10 H10 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C1 C6 1.357(6) . ? C1 C2 1.365(5) . ? C1 H1 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C12 C11 1.367(6) . ? C12 C13 1.385(6) . ? C12 H12 0.9300 . ? C2 H2 0.9300 . ? C6 H6 0.9300 . ? C11 H11 0.9300 . ? C13 H13 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 C19 O1 C20 123.2(3) . . ? C16 O4 N1 98.7(2) . . ? C4 N1 O4 111.0(2) . . ? C4 N1 C7 120.3(3) . . ? O4 N1 C7 102.3(2) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 N1 117.9(3) . . ? C3 C4 N1 122.8(3) . . ? O4 C16 C17 108.1(3) . . ? O4 C16 C18 105.7(3) . . ? C17 C16 C18 109.1(3) . . ? O4 C16 C15 104.1(2) . . ? C17 C16 C15 118.0(3) . . ? C18 C16 C15 111.0(3) . . ? O2 C19 O1 127.4(3) . . ? O2 C19 C18 120.4(3) . . ? O1 C19 C18 112.2(3) . . ? C14 C9 C10 120.2(3) . . ? C14 C9 C8 110.6(3) . . ? C10 C9 C8 129.2(3) . . ? C14 C15 C7 104.1(3) . . ? C14 C15 C16 115.5(3) . . ? C7 C15 C16 101.6(2) . . ? C14 C15 H15A 111.7 . . ? C7 C15 H15A 111.7 . . ? C16 C15 H15A 111.7 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C7 C8 115.8(3) . . ? N1 C7 C15 102.5(3) . . ? C8 C7 C15 107.2(3) . . ? N1 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? C15 C7 H7A 110.3 . . ? C9 C14 C13 119.9(3) . . ? C9 C14 C15 111.8(3) . . ? C13 C14 C15 128.3(3) . . ? O1 C20 C21 102.3(3) . . ? O1 C20 C22 111.3(3) . . ? C21 C20 C22 111.2(3) . . ? O1 C20 C23 108.0(3) . . ? C21 C20 C23 111.5(3) . . ? C22 C20 C23 112.0(3) . . ? O3 C18 C19 119.6(3) . . ? O3 C18 C16 123.6(3) . . ? C19 C18 C16 116.4(3) . . ? C9 C8 C7 105.3(3) . . ? C9 C8 H8A 110.7 . . ? C7 C8 H8A 110.7 . . ? C9 C8 H8B 110.7 . . ? C7 C8 H8B 110.7 . . ? H8A C8 H8B 108.8 . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C11 C10 C9 119.3(4) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C6 C1 C2 119.9(4) . . ? C6 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C11 C12 C13 120.6(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C1 C2 C3 120.4(4) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C1 C6 C5 120.7(4) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C10 C11 C12 121.3(4) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C12 C13 C14 118.7(4) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 O4 N1 C4 174.5(3) . . . . ? C16 O4 N1 C7 -56.0(3) . . . . ? O4 N1 C4 C5 175.4(3) . . . . ? C7 N1 C4 C5 56.2(4) . . . . ? O4 N1 C4 C3 -8.7(4) . . . . ? C7 N1 C4 C3 -128.0(3) . . . . ? N1 O4 C16 C17 173.3(2) . . . . ? N1 O4 C16 C18 -69.9(3) . . . . ? N1 O4 C16 C15 47.1(3) . . . . ? C20 O1 C19 O2 -2.5(5) . . . . ? C20 O1 C19 C18 175.4(3) . . . . ? O4 C16 C15 C14 90.0(3) . . . . ? C17 C16 C15 C14 -29.7(4) . . . . ? C18 C16 C15 C14 -156.7(3) . . . . ? O4 C16 C15 C7 -21.9(3) . . . . ? C17 C16 C15 C7 -141.6(3) . . . . ? C18 C16 C15 C7 91.4(3) . . . . ? C5 C4 C3 C2 1.6(5) . . . . ? N1 C4 C3 C2 -174.2(3) . . . . ? C4 N1 C7 C8 48.6(4) . . . . ? O4 N1 C7 C8 -74.9(3) . . . . ? C4 N1 C7 C15 164.9(3) . . . . ? O4 N1 C7 C15 41.4(3) . . . . ? C14 C15 C7 N1 -132.1(3) . . . . ? C16 C15 C7 N1 -11.9(3) . . . . ? C14 C15 C7 C8 -9.8(3) . . . . ? C16 C15 C7 C8 110.4(3) . . . . ? C10 C9 C14 C13 -2.6(5) . . . . ? C8 C9 C14 C13 176.4(3) . . . . ? C10 C9 C14 C15 179.1(3) . . . . ? C8 C9 C14 C15 -1.9(4) . . . . ? C7 C15 C14 C9 7.4(4) . . . . ? C16 C15 C14 C9 -103.0(3) . . . . ? C7 C15 C14 C13 -170.7(3) . . . . ? C16 C15 C14 C13 78.9(4) . . . . ? C19 O1 C20 C21 175.0(3) . . . . ? C19 O1 C20 C22 56.1(4) . . . . ? C19 O1 C20 C23 -67.3(4) . . . . ? O2 C19 C18 O3 88.8(4) . . . . ? O1 C19 C18 O3 -89.2(4) . . . . ? O2 C19 C18 C16 -83.8(4) . . . . ? O1 C19 C18 C16 98.1(3) . . . . ? O4 C16 C18 O3 152.1(3) . . . . ? C17 C16 C18 O3 -91.8(4) . . . . ? C15 C16 C18 O3 39.9(4) . . . . ? O4 C16 C18 C19 -35.5(4) . . . . ? C17 C16 C18 C19 80.6(3) . . . . ? C15 C16 C18 C19 -147.7(3) . . . . ? C14 C9 C8 C7 -4.5(4) . . . . ? C10 C9 C8 C7 174.4(3) . . . . ? N1 C7 C8 C9 122.5(3) . . . . ? C15 C7 C8 C9 8.9(4) . . . . ? C3 C4 C5 C6 -1.3(5) . . . . ? N1 C4 C5 C6 174.8(3) . . . . ? C14 C9 C10 C11 1.8(5) . . . . ? C8 C9 C10 C11 -177.0(4) . . . . ? C6 C1 C2 C3 0.0(6) . . . . ? C4 C3 C2 C1 -1.0(5) . . . . ? C2 C1 C6 C5 0.4(6) . . . . ? C4 C5 C6 C1 0.3(6) . . . . ? C9 C10 C11 C12 -0.5(6) . . . . ? C13 C12 C11 C10 0.0(6) . . . . ? C11 C12 C13 C14 -0.8(6) . . . . ? C9 C14 C13 C12 2.1(5) . . . . ? C15 C14 C13 C12 -179.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.247 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.062