# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_111123 _database_code_depnum_ccdc_archive 'CCDC 899391' #TrackingRef 'web_deposit_cif_file_0_ZiLiu_1346464895.111123.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 N O3' _chemical_formula_weight 359.41 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' O O 0.0492 0.0322 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 18.5722(6) _cell_length_b 6.3147(3) _cell_length_c 16.7573(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.197(3) _cell_angle_gamma 90.00 _cell_volume 1962.20(14) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 2942 _cell_measurement_theta_min 3.4550 _cell_measurement_theta_max 69.3958 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7871 _exptl_absorpt_correction_T_max 0.8638 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8531 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.77 _diffrn_reflns_theta_max 69.52 _reflns_number_total 3615 _reflns_number_gt 2540 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0869P)^2^+0.0867P] 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 0.0012(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3615 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1614 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.39089(6) 0.0468(3) 0.20563(8) 0.0733(4) Uani 1 1 d . . . O2 O 0.20768(6) 0.3737(3) 0.32977(8) 0.0764(4) Uani 1 1 d . . . N1 N 0.23536(9) -0.1475(3) 0.03465(10) 0.0728(5) Uani 1 1 d . . . C10 C 0.30076(8) 0.2192(3) 0.25973(11) 0.0619(5) Uani 1 1 d . . . O3 O 0.39407(8) -0.3224(3) 0.12841(11) 0.1073(6) Uani 1 1 d . . . C4 C 0.19143(9) 0.0037(3) 0.19594(11) 0.0600(5) Uani 1 1 d . . . C7 C 0.26912(9) 0.0548(3) 0.20929(11) 0.0616(5) Uani 1 1 d . . . C9 C 0.37355(9) 0.2081(4) 0.25399(11) 0.0670(5) Uani 1 1 d . . . C17 C 0.33652(10) -0.2284(4) 0.12546(12) 0.0722(6) Uani 1 1 d . . . C11 C 0.27074(9) 0.3718(3) 0.31387(11) 0.0639(5) Uani 1 1 d . . . C13 C 0.40133(10) 0.4497(4) 0.36683(12) 0.0727(6) Uani 1 1 d . . . C8 C 0.32622(9) -0.0456(4) 0.17689(11) 0.0675(5) Uani 1 1 d . . . C5 C 0.14350(10) 0.1554(4) 0.16589(13) 0.0735(6) Uani 1 1 d . . . H5 H 0.1592 0.2933 0.1581 0.088 Uiso 1 1 calc R . . C3 C 0.16518(10) -0.1960(4) 0.21037(14) 0.0774(6) Uani 1 1 d . . . H3 H 0.1962 -0.2992 0.2321 0.093 Uiso 1 1 calc R . . C14 C 0.42990(9) 0.3443(4) 0.29187(12) 0.0762(6) Uani 1 1 d . . . H14A H 0.4436 0.4523 0.2544 0.091 Uiso 1 1 calc R . . H14B H 0.4723 0.2602 0.3067 0.091 Uiso 1 1 calc R . . C18 C 0.27692(10) -0.2984(3) 0.06846(11) 0.0662(5) Uani 1 1 d . . . C1 C 0.04642(10) -0.0982(4) 0.16021(15) 0.0843(7) Uani 1 1 d . . . C22 C 0.18429(13) -0.2122(5) -0.01918(14) 0.0882(7) Uani 1 1 d . . . H22 H 0.1549 -0.1103 -0.0444 0.106 Uiso 1 1 calc R . . C2 C 0.09360(11) -0.2452(4) 0.19304(16) 0.0870(7) Uani 1 1 d . . . H2 H 0.0771 -0.3806 0.2039 0.104 Uiso 1 1 calc R . . C12 C 0.32469(10) 0.5331(4) 0.34709(13) 0.0746(6) Uani 1 1 d . . . H12B H 0.3065 0.5928 0.3954 0.090 Uiso 1 1 calc R . . H12A H 0.3275 0.6472 0.3086 0.090 Uiso 1 1 calc R . . C6 C 0.07223(11) 0.1026(4) 0.14744(15) 0.0857(7) Uani 1 1 d . . . H6 H 0.0410 0.2054 0.1259 0.103 Uiso 1 1 calc R . . C15 C 0.45019(13) 0.6358(4) 0.39246(17) 0.0994(9) Uani 1 1 d . . . H15A H 0.4509 0.7368 0.3497 0.149 Uiso 1 1 calc R . . H15C H 0.4982 0.5850 0.4050 0.149 Uiso 1 1 calc R . . H15B H 0.4321 0.7023 0.4388 0.149 Uiso 1 1 calc R . . C19 C 0.26898(14) -0.5110(4) 0.05109(14) 0.0855(6) Uani 1 1 d . . . H H 0.2993 -0.6109 0.0762 0.103 Uiso 1 1 calc R . . C16 C 0.40027(13) 0.2881(5) 0.43468(14) 0.0963(8) Uani 1 1 d . . . H16B H 0.3815 0.3535 0.4809 0.145 Uiso 1 1 calc R . . H16C H 0.4484 0.2387 0.4475 0.145 Uiso 1 1 calc R . . H16A H 0.3702 0.1706 0.4182 0.145 Uiso 1 1 calc R . . C20 C 0.21553(16) -0.5723(5) -0.00401(17) 0.1012(8) Uani 1 1 d . . . H20 H 0.2087 -0.7144 -0.0169 0.121 Uiso 1 1 calc R . . C21 C 0.17275(15) -0.4202(5) -0.03933(16) 0.1001(9) Uani 1 1 d . . . H21 H 0.1360 -0.4570 -0.0768 0.120 Uiso 1 1 calc R . . C23 C -0.03132(13) -0.1575(6) 0.1374(2) 0.1292(12) Uani 1 1 d . . . H24B H -0.0628 -0.0488 0.1552 0.194 Uiso 1 1 calc R . . H24C H -0.0427 -0.2894 0.1623 0.194 Uiso 1 1 calc R . . H24A H -0.0376 -0.1718 0.0804 0.194 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 0.0378(6) 0.1075(12) 0.0742(8) -0.0164(8) -0.0005(5) 0.0002(6) O2 0.0420(7) 0.1052(12) 0.0822(9) -0.0105(8) 0.0043(6) 0.0027(6) N1 0.0645(10) 0.0805(12) 0.0722(10) 0.0043(9) -0.0069(8) -0.0089(8) C10 0.0369(8) 0.0891(14) 0.0592(10) -0.0032(9) -0.0017(7) -0.0019(8) O3 0.0652(10) 0.1356(16) 0.1193(14) -0.0309(12) -0.0106(9) 0.0311(10) C4 0.0389(8) 0.0776(13) 0.0627(10) 0.0006(9) -0.0029(7) -0.0017(8) C7 0.0407(9) 0.0826(13) 0.0609(10) 0.0025(9) -0.0027(7) 0.0003(8) C9 0.0406(9) 0.0996(16) 0.0604(10) -0.0083(10) -0.0001(7) -0.0008(9) C17 0.0517(10) 0.0944(16) 0.0704(11) -0.0042(10) 0.0014(8) 0.0082(10) C11 0.0418(9) 0.0877(14) 0.0615(10) 0.0018(9) -0.0025(7) 0.0014(8) C13 0.0455(9) 0.1058(17) 0.0661(11) -0.0102(11) -0.0035(8) -0.0092(10) C8 0.0414(9) 0.0945(15) 0.0657(11) -0.0059(10) -0.0044(7) 0.0006(9) C5 0.0479(10) 0.0788(14) 0.0926(14) 0.0014(11) -0.0065(9) 0.0018(9) C3 0.0502(10) 0.0868(16) 0.0947(15) 0.0147(12) -0.0016(9) -0.0010(10) C14 0.0395(9) 0.1149(18) 0.0734(12) -0.0118(12) -0.0031(8) -0.0073(10) C18 0.0568(10) 0.0796(14) 0.0628(10) -0.0042(10) 0.0093(8) -0.0017(10) C1 0.0441(10) 0.1070(19) 0.1010(16) -0.0128(13) -0.0035(10) -0.0082(11) C22 0.0754(14) 0.1047(19) 0.0824(14) 0.0069(13) -0.0152(11) -0.0169(13) C2 0.0567(12) 0.0893(16) 0.1151(19) 0.0060(13) 0.0039(11) -0.0143(11) C12 0.0525(10) 0.0982(16) 0.0729(12) -0.0142(11) 0.0007(9) -0.0042(10) C6 0.0456(10) 0.1004(18) 0.1092(17) 0.0016(13) -0.0137(10) 0.0093(11) C15 0.0623(13) 0.135(2) 0.1001(17) -0.0330(16) -0.0018(11) -0.0236(14) C19 0.0956(17) 0.0796(16) 0.0819(14) -0.0053(12) 0.0107(12) 0.0039(13) C16 0.0732(14) 0.144(2) 0.0704(13) 0.0000(14) -0.0117(10) -0.0034(14) C20 0.117(2) 0.0882(19) 0.0996(18) -0.0230(15) 0.0127(16) -0.0266(16) C21 0.0973(18) 0.115(2) 0.0863(16) -0.0105(15) -0.0080(13) -0.0392(17) C23 0.0507(13) 0.170(3) 0.164(3) -0.026(2) -0.0159(15) -0.0215(16) _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 1.352(2) . ? O1 C8 1.397(2) . ? O2 C11 1.215(2) . ? N1 C18 1.333(3) . ? N1 C22 1.336(3) . ? C10 C9 1.362(2) . ? C10 C7 1.443(3) . ? C10 C11 1.456(3) . ? O3 C17 1.221(2) . ? C4 C3 1.379(3) . ? C4 C5 1.383(3) . ? C4 C7 1.483(2) . ? C7 C8 1.373(3) . ? C9 C14 1.471(3) . ? C17 C8 1.460(3) . ? C17 C18 1.488(3) . ? C11 C12 1.513(3) . ? C13 C16 1.529(3) . ? C13 C15 1.532(3) . ? C13 C12 1.536(3) . ? C13 C14 1.542(3) . ? C5 C6 1.383(3) . ? C5 H5 0.9300 . ? C3 C2 1.380(3) . ? C3 H3 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C18 C19 1.380(3) . ? C1 C2 1.370(3) . ? C1 C6 1.377(3) . ? C1 C23 1.520(3) . ? C22 C21 1.370(4) . ? C22 H22 0.9300 . ? C2 H2 0.9300 . ? C12 H12B 0.9700 . ? C12 H12A 0.9700 . ? C6 H6 0.9300 . ? C15 H15A 0.9600 . ? C15 H15C 0.9600 . ? C15 H15B 0.9600 . ? C19 C20 1.373(3) . ? C19 H 0.9300 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C16 H16A 0.9600 . ? C20 C21 1.361(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C23 H24B 0.9600 . ? C23 H24C 0.9600 . ? C23 H24A 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 C8 107.01(13) . . ? C18 N1 C22 116.2(2) . . ? C9 C10 C7 107.17(17) . . ? C9 C10 C11 119.59(17) . . ? C7 C10 C11 133.14(15) . . ? C3 C4 C5 118.08(17) . . ? C3 C4 C7 121.54(18) . . ? C5 C4 C7 120.35(18) . . ? C8 C7 C10 105.39(15) . . ? C8 C7 C4 127.31(19) . . ? C10 C7 C4 127.29(17) . . ? O1 C9 C10 110.58(16) . . ? O1 C9 C14 120.78(15) . . ? C10 C9 C14 128.64(19) . . ? O3 C17 C8 120.24(19) . . ? O3 C17 C18 120.0(2) . . ? C8 C17 C18 119.78(17) . . ? O2 C11 C10 123.38(18) . . ? O2 C11 C12 122.63(19) . . ? C10 C11 C12 113.97(15) . . ? C16 C13 C15 109.61(18) . . ? C16 C13 C12 109.81(17) . . ? C15 C13 C12 108.9(2) . . ? C16 C13 C14 109.7(2) . . ? C15 C13 C14 109.52(17) . . ? C12 C13 C14 109.24(15) . . ? C7 C8 O1 109.81(18) . . ? C7 C8 C17 136.73(18) . . ? O1 C8 C17 113.31(15) . . ? C6 C5 C4 120.2(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C9 C14 C13 109.58(15) . . ? C9 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? C9 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 108.2 . . ? N1 C18 C19 123.6(2) . . ? N1 C18 C17 116.94(19) . . ? C19 C18 C17 119.4(2) . . ? C2 C1 C6 117.77(19) . . ? C2 C1 C23 120.8(2) . . ? C6 C1 C23 121.5(2) . . ? N1 C22 C21 123.7(3) . . ? N1 C22 H22 118.1 . . ? C21 C22 H22 118.1 . . ? C1 C2 C3 121.3(2) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C11 C12 C13 115.8(2) . . ? C11 C12 H12B 108.3 . . ? C13 C12 H12B 108.3 . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12A 108.3 . . ? H12B C12 H12A 107.4 . . ? C1 C6 C5 121.6(2) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? H15C C15 H15B 109.5 . . ? C20 C19 C18 118.7(2) . . ? C20 C19 H 120.6 . . ? C18 C19 H 120.6 . . ? C13 C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? C21 C20 C19 118.5(3) . . ? C21 C20 H20 120.8 . . ? C19 C20 H20 120.8 . . ? C20 C21 C22 119.3(2) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C1 C23 H24B 109.5 . . ? C1 C23 H24C 109.5 . . ? H24B C23 H24C 109.5 . . ? C1 C23 H24A 109.5 . . ? H24B C23 H24A 109.5 . . ? H24C C23 H24A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C10 C7 C8 0.5(2) . . . . ? C11 C10 C7 C8 -175.8(2) . . . . ? C9 C10 C7 C4 179.88(19) . . . . ? C11 C10 C7 C4 3.7(4) . . . . ? C3 C4 C7 C8 55.7(3) . . . . ? C5 C4 C7 C8 -122.1(2) . . . . ? C3 C4 C7 C10 -123.6(2) . . . . ? C5 C4 C7 C10 58.6(3) . . . . ? C8 O1 C9 C10 2.0(2) . . . . ? C8 O1 C9 C14 -177.67(18) . . . . ? C7 C10 C9 O1 -1.5(2) . . . . ? C11 C10 C9 O1 175.29(18) . . . . ? C7 C10 C9 C14 178.1(2) . . . . ? C11 C10 C9 C14 -5.1(3) . . . . ? C9 C10 C11 O2 -170.5(2) . . . . ? C7 C10 C11 O2 5.3(4) . . . . ? C9 C10 C11 C12 11.1(3) . . . . ? C7 C10 C11 C12 -173.0(2) . . . . ? C10 C7 C8 O1 0.8(2) . . . . ? C4 C7 C8 O1 -178.67(17) . . . . ? C10 C7 C8 C17 175.8(2) . . . . ? C4 C7 C8 C17 -3.6(4) . . . . ? C9 O1 C8 C7 -1.7(2) . . . . ? C9 O1 C8 C17 -178.04(18) . . . . ? O3 C17 C8 C7 -154.7(3) . . . . ? C18 C17 C8 C7 26.2(4) . . . . ? O3 C17 C8 O1 20.3(3) . . . . ? C18 C17 C8 O1 -158.84(18) . . . . ? C3 C4 C5 C6 -3.2(3) . . . . ? C7 C4 C5 C6 174.8(2) . . . . ? C5 C4 C3 C2 2.0(3) . . . . ? C7 C4 C3 C2 -175.9(2) . . . . ? O1 C9 C14 C13 -157.3(2) . . . . ? C10 C9 C14 C13 23.1(3) . . . . ? C16 C13 C14 C9 75.6(2) . . . . ? C15 C13 C14 C9 -164.1(2) . . . . ? C12 C13 C14 C9 -44.8(3) . . . . ? C22 N1 C18 C19 -0.6(3) . . . . ? C22 N1 C18 C17 176.94(18) . . . . ? O3 C17 C18 N1 -143.8(2) . . . . ? C8 C17 C18 N1 35.3(3) . . . . ? O3 C17 C18 C19 33.8(3) . . . . ? C8 C17 C18 C19 -147.0(2) . . . . ? C18 N1 C22 C21 1.0(3) . . . . ? C6 C1 C2 C3 -2.1(4) . . . . ? C23 C1 C2 C3 176.8(3) . . . . ? C4 C3 C2 C1 0.7(4) . . . . ? O2 C11 C12 C13 144.06(19) . . . . ? C10 C11 C12 C13 -37.6(2) . . . . ? C16 C13 C12 C11 -64.9(2) . . . . ? C15 C13 C12 C11 175.00(18) . . . . ? C14 C13 C12 C11 55.4(2) . . . . ? C2 C1 C6 C5 0.9(4) . . . . ? C23 C1 C6 C5 -178.0(2) . . . . ? C4 C5 C6 C1 1.8(4) . . . . ? N1 C18 C19 C20 0.0(3) . . . . ? C17 C18 C19 C20 -177.4(2) . . . . ? C18 C19 C20 C21 0.2(4) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? N1 C22 C21 C20 -0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 69.52 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.210 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.032