# 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_sa1765 _database_code_depnum_ccdc_archive 'CCDC 857572' #TrackingRef 'sa1765.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H19 Cl N2 O3' _chemical_formula_sum 'C28 H19 Cl N2 O3' _chemical_formula_weight 466.90 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.592(2) _cell_length_b 10.080(3) _cell_length_c 11.857(3) _cell_angle_alpha 89.893(10) _cell_angle_beta 76.026(7) _cell_angle_gamma 80.083(8) _cell_volume 1095.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3813 _cell_measurement_theta_min 1.77 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9359 _exptl_absorpt_correction_T_max 0.9753 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14459 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5004 _reflns_number_gt 4574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELX97 (Sheldrick, 2008)' _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^)+(0.0365P)^2^+0.5168P] 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 5004 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 Cl1 Cl 0.93400(7) 0.18782(8) -0.19695(5) 0.0627(2) Uani 1 1 d . . . O1 O 0.55739(16) -0.17546(14) 0.19599(12) 0.0386(3) Uani 1 1 d . . . O2 O 0.88334(14) -0.15357(13) 0.50000(12) 0.0333(3) Uani 1 1 d . . . O3 O 0.43450(15) 0.43418(13) 0.40145(11) 0.0339(3) Uani 1 1 d . . . N1 N 0.70614(16) 0.08399(14) 0.46099(12) 0.0247(3) Uani 1 1 d . . . N2 N 0.60647(17) 0.29411(16) 0.52143(13) 0.0296(3) Uani 1 1 d . . . H2 H 0.5468 0.3721 0.5296 0.035 Uiso 1 1 calc R . . C1 C 0.56374(18) 0.08288(17) 0.27325(14) 0.0237(4) Uani 1 1 d . . . H1 H 0.4685 0.0654 0.2616 0.028 Uiso 1 1 calc R . . C2 C 0.53137(19) 0.20339(17) 0.35886(15) 0.0246(4) Uani 1 1 d . . . C3 C 0.60932(19) 0.19819(17) 0.44404(14) 0.0239(4) Uani 1 1 d . . . C4 C 0.7112(2) 0.25800(19) 0.59139(16) 0.0310(4) Uani 1 1 d . . . H4A H 0.6649 0.2775 0.6752 0.037 Uiso 1 1 calc R . . H4B H 0.7941 0.3069 0.5681 0.037 Uiso 1 1 calc R . . C5 C 0.7608(2) 0.10692(19) 0.56495(16) 0.0301(4) Uani 1 1 d . . . H5B H 0.8685 0.0821 0.5477 0.036 Uiso 1 1 calc R . . H5A H 0.7172 0.0546 0.6308 0.036 Uiso 1 1 calc R . . C6 C 0.70844(18) -0.03774(17) 0.40659(15) 0.0235(4) Uani 1 1 d . . . C7 C 0.63634(18) -0.04251(17) 0.32104(15) 0.0239(4) Uani 1 1 d . . . C8 C 0.63131(19) -0.17136(18) 0.26713(16) 0.0272(4) Uani 1 1 d . . . C9 C 0.71558(19) -0.29683(18) 0.29973(16) 0.0273(4) Uani 1 1 d . . . C10 C 0.79630(19) -0.29162(18) 0.38215(15) 0.0268(4) Uani 1 1 d . . . C11 C 0.80148(19) -0.16135(18) 0.43681(15) 0.0255(4) Uani 1 1 d . . . C12 C 0.8783(2) -0.4095(2) 0.41029(17) 0.0357(4) Uani 1 1 d . . . H12 H 0.9333 -0.4061 0.4666 0.043 Uiso 1 1 calc R . . C13 C 0.8795(2) -0.5313(2) 0.35615(19) 0.0411(5) Uani 1 1 d . . . H13 H 0.9353 -0.6116 0.3753 0.049 Uiso 1 1 calc R . . C14 C 0.7993(3) -0.5361(2) 0.2741(2) 0.0429(5) Uani 1 1 d . . . H14 H 0.8006 -0.6198 0.2368 0.051 Uiso 1 1 calc R . . C15 C 0.7173(2) -0.4196(2) 0.24594(18) 0.0359(4) Uani 1 1 d . . . H15 H 0.6621 -0.4236 0.1898 0.043 Uiso 1 1 calc R . . C16 C 0.65833(19) 0.10880(17) 0.15425(15) 0.0242(4) Uani 1 1 d . . . C17 C 0.8030(2) 0.12392(18) 0.14061(16) 0.0285(4) Uani 1 1 d . . . H17 H 0.8439 0.1174 0.2062 0.034 Uiso 1 1 calc R . . C18 C 0.8880(2) 0.1482(2) 0.03341(17) 0.0339(4) Uani 1 1 d . . . H18 H 0.9864 0.1589 0.0251 0.041 Uiso 1 1 calc R . . C19 C 0.8276(2) 0.1567(2) -0.06124(16) 0.0355(4) Uani 1 1 d . . . C20 C 0.6857(2) 0.1420(2) -0.05109(17) 0.0397(5) Uani 1 1 d . . . H20 H 0.6456 0.1482 -0.1172 0.048 Uiso 1 1 calc R . . C21 C 0.6016(2) 0.1180(2) 0.05693(16) 0.0325(4) Uani 1 1 d . . . H21 H 0.5032 0.1076 0.0645 0.039 Uiso 1 1 calc R . . C22 C 0.44262(19) 0.32859(18) 0.34352(15) 0.0268(4) Uani 1 1 d . . . C23 C 0.3569(2) 0.33879(19) 0.25157(15) 0.0293(4) Uani 1 1 d . . . C24 C 0.2617(2) 0.2517(2) 0.24434(17) 0.0341(4) Uani 1 1 d . . . H24 H 0.2500 0.1821 0.2981 0.041 Uiso 1 1 calc R . . C25 C 0.1834(2) 0.2654(3) 0.15937(19) 0.0453(5) Uani 1 1 d . . . H25 H 0.1183 0.2054 0.1552 0.054 Uiso 1 1 calc R . . C26 C 0.2001(3) 0.3658(3) 0.0812(2) 0.0515(6) Uani 1 1 d . . . H26 H 0.1481 0.3739 0.0220 0.062 Uiso 1 1 calc R . . C27 C 0.2922(3) 0.4547(2) 0.0884(2) 0.0505(6) Uani 1 1 d . . . H27 H 0.3027 0.5246 0.0348 0.061 Uiso 1 1 calc R . . C28 C 0.3695(2) 0.4420(2) 0.17394(18) 0.0391(5) Uani 1 1 d . . . H28 H 0.4315 0.5044 0.1795 0.047 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 Cl1 0.0396(3) 0.1096(6) 0.0324(3) 0.0230(3) -0.0001(2) -0.0078(3) O1 0.0433(8) 0.0346(8) 0.0449(8) -0.0049(6) -0.0243(7) -0.0064(6) O2 0.0327(7) 0.0357(7) 0.0342(7) 0.0019(6) -0.0160(6) -0.0026(6) O3 0.0413(8) 0.0280(7) 0.0320(7) -0.0044(6) -0.0131(6) 0.0014(6) N1 0.0270(7) 0.0250(7) 0.0238(7) 0.0001(6) -0.0108(6) -0.0022(6) N2 0.0336(8) 0.0297(8) 0.0263(8) -0.0037(6) -0.0120(6) -0.0010(6) C1 0.0226(8) 0.0261(9) 0.0228(8) 0.0000(7) -0.0068(7) -0.0039(7) C2 0.0260(9) 0.0260(9) 0.0215(8) 0.0005(7) -0.0057(7) -0.0042(7) C3 0.0242(8) 0.0249(9) 0.0212(8) 0.0003(7) -0.0039(7) -0.0032(7) C4 0.0361(10) 0.0332(10) 0.0277(9) 0.0005(8) -0.0140(8) -0.0082(8) C5 0.0334(10) 0.0335(10) 0.0260(9) -0.0010(7) -0.0127(8) -0.0053(8) C6 0.0213(8) 0.0252(9) 0.0236(8) 0.0006(7) -0.0037(7) -0.0054(6) C7 0.0209(8) 0.0263(9) 0.0237(8) 0.0005(7) -0.0041(7) -0.0035(7) C8 0.0251(9) 0.0295(9) 0.0277(9) 0.0006(7) -0.0062(7) -0.0066(7) C9 0.0259(9) 0.0259(9) 0.0287(9) 0.0006(7) -0.0024(7) -0.0067(7) C10 0.0243(9) 0.0273(9) 0.0263(9) 0.0016(7) -0.0015(7) -0.0044(7) C11 0.0234(8) 0.0281(9) 0.0235(8) 0.0041(7) -0.0033(7) -0.0041(7) C12 0.0375(11) 0.0339(10) 0.0336(10) 0.0046(8) -0.0092(9) 0.0002(8) C13 0.0473(12) 0.0273(10) 0.0434(12) 0.0025(9) -0.0073(10) 0.0028(9) C14 0.0524(13) 0.0260(10) 0.0471(12) -0.0046(9) -0.0082(10) -0.0040(9) C15 0.0376(11) 0.0314(10) 0.0385(11) -0.0037(8) -0.0083(9) -0.0072(8) C16 0.0272(9) 0.0223(8) 0.0227(8) -0.0011(7) -0.0061(7) -0.0032(7) C17 0.0294(9) 0.0331(10) 0.0254(9) -0.0001(7) -0.0102(7) -0.0076(7) C18 0.0279(9) 0.0433(11) 0.0320(10) 0.0025(8) -0.0077(8) -0.0097(8) C19 0.0317(10) 0.0467(12) 0.0242(9) 0.0054(8) -0.0018(8) -0.0033(8) C20 0.0323(10) 0.0621(14) 0.0243(9) 0.0021(9) -0.0110(8) -0.0017(9) C21 0.0244(9) 0.0477(12) 0.0259(9) 0.0006(8) -0.0079(7) -0.0055(8) C22 0.0272(9) 0.0296(9) 0.0214(8) -0.0001(7) -0.0038(7) -0.0017(7) C23 0.0288(9) 0.0318(10) 0.0244(9) -0.0018(7) -0.0066(7) 0.0030(7) C24 0.0265(9) 0.0442(11) 0.0298(10) 0.0024(8) -0.0068(8) -0.0018(8) C25 0.0333(11) 0.0672(15) 0.0381(11) 0.0011(11) -0.0140(9) -0.0091(10) C26 0.0503(14) 0.0713(17) 0.0379(12) 0.0056(11) -0.0260(11) -0.0032(12) C27 0.0645(16) 0.0525(14) 0.0362(12) 0.0129(10) -0.0210(11) -0.0028(12) C28 0.0470(12) 0.0372(11) 0.0346(11) 0.0023(9) -0.0155(9) -0.0032(9) _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 Cl1 C19 1.745(2) . ? O1 C8 1.231(2) . ? O2 C11 1.221(2) . ? O3 C22 1.249(2) . ? N1 C6 1.382(2) . ? N1 C3 1.396(2) . ? N1 C5 1.484(2) . ? N2 C3 1.326(2) . ? N2 C4 1.451(2) . ? N2 H2 0.8800 . ? C1 C7 1.513(2) . ? C1 C2 1.525(2) . ? C1 C16 1.531(2) . ? C1 H1 1.0000 . ? C2 C3 1.390(2) . ? C2 C22 1.433(2) . ? C4 C5 1.525(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C6 C7 1.364(2) . ? C6 C11 1.499(2) . ? C7 C8 1.462(2) . ? C8 C9 1.483(3) . ? C9 C15 1.389(3) . ? C9 C10 1.392(3) . ? C10 C12 1.394(3) . ? C10 C11 1.479(3) . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.386(2) . ? C16 C17 1.393(2) . ? C17 C18 1.381(3) . ? C17 H17 0.9500 . ? C18 C19 1.378(3) . ? C18 H18 0.9500 . ? C19 C20 1.371(3) . ? C20 C21 1.384(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.510(2) . ? C23 C24 1.387(3) . ? C23 C28 1.389(3) . ? C24 C25 1.388(3) . ? C24 H24 0.9500 . ? C25 C26 1.375(3) . ? C25 H25 0.9500 . ? C26 C27 1.378(4) . ? C26 H26 0.9500 . ? C27 C28 1.387(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C3 119.85(14) . . ? C6 N1 C5 127.74(14) . . ? C3 N1 C5 109.77(14) . . ? C3 N2 C4 113.54(15) . . ? C3 N2 H2 123.2 . . ? C4 N2 H2 123.2 . . ? C7 C1 C2 111.25(14) . . ? C7 C1 C16 109.51(14) . . ? C2 C1 C16 112.55(14) . . ? C7 C1 H1 107.8 . . ? C2 C1 H1 107.8 . . ? C16 C1 H1 107.8 . . ? C3 C2 C22 118.61(16) . . ? C3 C2 C1 118.10(15) . . ? C22 C2 C1 122.49(15) . . ? N2 C3 C2 128.23(16) . . ? N2 C3 N1 108.62(15) . . ? C2 C3 N1 123.16(15) . . ? N2 C4 C5 102.96(14) . . ? N2 C4 H4A 111.2 . . ? C5 C4 H4A 111.2 . . ? N2 C4 H4B 111.2 . . ? C5 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? N1 C5 C4 103.01(14) . . ? N1 C5 H5B 111.2 . . ? C4 C5 H5B 111.2 . . ? N1 C5 H5A 111.2 . . ? C4 C5 H5A 111.2 . . ? H5B C5 H5A 109.1 . . ? C7 C6 N1 120.23(15) . . ? C7 C6 C11 121.10(16) . . ? N1 C6 C11 118.49(15) . . ? C6 C7 C8 120.78(16) . . ? C6 C7 C1 122.68(15) . . ? C8 C7 C1 116.49(15) . . ? O1 C8 C7 120.28(16) . . ? O1 C8 C9 120.52(16) . . ? C7 C8 C9 119.20(15) . . ? C15 C9 C10 119.71(17) . . ? C15 C9 C8 120.12(17) . . ? C10 C9 C8 120.15(16) . . ? C9 C10 C12 119.89(17) . . ? C9 C10 C11 120.72(16) . . ? C12 C10 C11 119.34(17) . . ? O2 C11 C10 121.36(16) . . ? O2 C11 C6 121.01(16) . . ? C10 C11 C6 117.54(15) . . ? C13 C12 C10 120.00(19) . . ? C13 C12 H12 120.0 . . ? C10 C12 H12 120.0 . . ? C12 C13 C14 119.97(19) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 120.36(19) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C9 120.06(19) . . ? C14 C15 H15 120.0 . . ? C9 C15 H15 120.0 . . ? C21 C16 C17 118.20(16) . . ? C21 C16 C1 120.60(16) . . ? C17 C16 C1 121.20(15) . . ? C18 C17 C16 121.20(17) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 118.85(18) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C20 C19 C18 121.54(18) . . ? C20 C19 Cl1 119.27(15) . . ? C18 C19 Cl1 119.19(16) . . ? C19 C20 C21 119.00(18) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C20 C21 C16 121.22(18) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? O3 C22 C2 123.01(16) . . ? O3 C22 C23 116.65(16) . . ? C2 C22 C23 120.31(15) . . ? C24 C23 C28 118.66(18) . . ? C24 C23 C22 122.38(17) . . ? C28 C23 C22 118.92(18) . . ? C23 C24 C25 120.7(2) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 119.9(2) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.2(2) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C26 C27 C28 120.0(2) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C27 C28 C23 120.6(2) . . ? C27 C28 H28 119.7 . . ? C23 C28 H28 119.7 . . ? 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 C7 C1 C2 C3 20.6(2) . . . . ? C16 C1 C2 C3 -102.76(18) . . . . ? C7 C1 C2 C22 -169.81(15) . . . . ? C16 C1 C2 C22 66.9(2) . . . . ? C4 N2 C3 C2 -175.13(18) . . . . ? C4 N2 C3 N1 5.3(2) . . . . ? C22 C2 C3 N2 4.8(3) . . . . ? C1 C2 C3 N2 174.84(17) . . . . ? C22 C2 C3 N1 -175.69(16) . . . . ? C1 C2 C3 N1 -5.6(3) . . . . ? C6 N1 C3 N2 167.78(15) . . . . ? C5 N1 C3 N2 4.8(2) . . . . ? C6 N1 C3 C2 -11.8(3) . . . . ? C5 N1 C3 C2 -174.82(16) . . . . ? C3 N2 C4 C5 -12.6(2) . . . . ? C6 N1 C5 C4 -173.27(16) . . . . ? C3 N1 C5 C4 -11.97(19) . . . . ? N2 C4 C5 N1 13.94(18) . . . . ? C3 N1 C6 C7 11.7(2) . . . . ? C5 N1 C6 C7 171.30(16) . . . . ? C3 N1 C6 C11 -173.32(15) . . . . ? C5 N1 C6 C11 -13.7(3) . . . . ? N1 C6 C7 C8 -176.68(15) . . . . ? C11 C6 C7 C8 8.4(2) . . . . ? N1 C6 C7 C1 6.0(3) . . . . ? C11 C6 C7 C1 -168.85(15) . . . . ? C2 C1 C7 C6 -21.5(2) . . . . ? C16 C1 C7 C6 103.58(18) . . . . ? C2 C1 C7 C8 161.14(15) . . . . ? C16 C1 C7 C8 -73.81(18) . . . . ? C6 C7 C8 O1 174.80(17) . . . . ? C1 C7 C8 O1 -7.8(2) . . . . ? C6 C7 C8 C9 -4.9(2) . . . . ? C1 C7 C8 C9 172.58(15) . . . . ? O1 C8 C9 C15 3.1(3) . . . . ? C7 C8 C9 C15 -177.26(17) . . . . ? O1 C8 C9 C10 -178.58(17) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C15 C9 C10 C12 0.0(3) . . . . ? C8 C9 C10 C12 -178.38(17) . . . . ? C15 C9 C10 C11 177.27(17) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 O2 -172.36(17) . . . . ? C12 C10 C11 O2 5.0(3) . . . . ? C9 C10 C11 C6 4.3(2) . . . . ? C12 C10 C11 C6 -178.34(16) . . . . ? C7 C6 C11 O2 168.58(17) . . . . ? N1 C6 C11 O2 -6.4(2) . . . . ? C7 C6 C11 C10 -8.1(2) . . . . ? N1 C6 C11 C10 176.88(15) . . . . ? C9 C10 C12 C13 0.1(3) . . . . ? C11 C10 C12 C13 -177.22(18) . . . . ? C10 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C13 C14 C15 C9 0.3(3) . . . . ? C10 C9 C15 C14 -0.2(3) . . . . ? C8 C9 C15 C14 178.18(18) . . . . ? C7 C1 C16 C21 123.12(18) . . . . ? C2 C1 C16 C21 -112.58(18) . . . . ? C7 C1 C16 C17 -57.0(2) . . . . ? C2 C1 C16 C17 67.3(2) . . . . ? C21 C16 C17 C18 0.4(3) . . . . ? C1 C16 C17 C18 -179.55(17) . . . . ? C16 C17 C18 C19 -0.4(3) . . . . ? C17 C18 C19 C20 0.2(3) . . . . ? C17 C18 C19 Cl1 179.81(15) . . . . ? C18 C19 C20 C21 -0.1(3) . . . . ? Cl1 C19 C20 C21 -179.67(16) . . . . ? C19 C20 C21 C16 0.1(3) . . . . ? C17 C16 C21 C20 -0.2(3) . . . . ? C1 C16 C21 C20 179.70(18) . . . . ? C3 C2 C22 O3 1.6(3) . . . . ? C1 C2 C22 O3 -167.96(16) . . . . ? C3 C2 C22 C23 179.67(16) . . . . ? C1 C2 C22 C23 10.1(3) . . . . ? O3 C22 C23 C24 -128.40(19) . . . . ? C2 C22 C23 C24 53.4(2) . . . . ? O3 C22 C23 C28 49.2(2) . . . . ? C2 C22 C23 C28 -128.98(19) . . . . ? C28 C23 C24 C25 1.6(3) . . . . ? C22 C23 C24 C25 179.22(18) . . . . ? C23 C24 C25 C26 0.1(3) . . . . ? C24 C25 C26 C27 -1.3(4) . . . . ? C25 C26 C27 C28 0.7(4) . . . . ? C26 C27 C28 C23 1.1(4) . . . . ? C24 C23 C28 C27 -2.2(3) . . . . ? C22 C23 C28 C27 -179.90(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O3 0.88 2.10 2.657(2) 120.5 . N2 H2 O3 0.88 2.17 2.821(2) 130.3 2_666 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.281 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.044 data_a _database_code_depnum_ccdc_archive 'CCDC 909448' #TrackingRef 'web_deposit_cif_file_0_QiangWang_1352184297.VI 16B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 O4' _chemical_formula_sum 'C17 H18 O4' _chemical_formula_weight 286.31 _symmetry_space_group_name_Hall '-P 2ybc' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/C 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 9.4369(19) _cell_length_b 17.895(4) _cell_length_c 8.6611(17) _cell_angle_alpha 90.00 _cell_angle_beta 91.58(3) _cell_angle_gamma 90.00 _cell_volume 1462.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4101 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8887 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 APEX CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7987 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2556 _reflns_number_gt 2213 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0640P)^2^+0.2179P] 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 2556 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 O2 O 0.82422(15) 1.06010(7) 0.40156(16) 0.0579(4) Uani 1 1 d . . . O3 O 0.75499(14) 0.94759(7) 0.31024(17) 0.0579(4) Uani 1 1 d . . . O4 O 0.95353(16) 0.79725(8) 0.28003(16) 0.0618(4) Uani 1 1 d . . . C10 C 0.89166(19) 0.81762(10) 0.1636(2) 0.0425(4) Uani 1 1 d . . . C9 C 0.93442(19) 0.88683(10) 0.0777(2) 0.0434(4) Uani 1 1 d . . . H9A H 0.9720 0.8717 -0.0206 0.052 Uiso 1 1 calc R . . H9B H 0.8499 0.9163 0.0558 0.052 Uiso 1 1 calc R . . O1 O 1.17995(17) 1.08326(8) 0.29412(18) 0.0658(4) Uani 1 1 d . . . C8 C 1.0423(2) 0.93631(10) 0.1586(2) 0.0430(4) Uani 1 1 d . . . C7 C 1.1814(2) 0.93233(11) 0.1331(2) 0.0506(5) Uani 1 1 d . . . H7 H 1.2379 0.9648 0.1917 0.061 Uiso 1 1 calc R . . C13 C 1.0574(2) 1.06226(10) 0.3114(2) 0.0512(5) Uani 1 1 d . . . C12 C 0.9868(2) 0.99494(10) 0.2596(2) 0.0446(5) Uani 1 1 d . . . C15 C 0.8543(2) 0.99887(10) 0.3206(2) 0.0483(5) Uani 1 1 d . . . C14 C 0.9486(2) 1.10750(11) 0.3955(3) 0.0593(6) Uani 1 1 d . . . H14A H 0.9831 1.1200 0.4989 0.071 Uiso 1 1 calc R . . H14B H 0.9268 1.1534 0.3402 0.071 Uiso 1 1 calc R . . C6 C 1.2581(2) 0.88392(11) 0.0259(2) 0.0497(5) Uani 1 1 d . . . C1 C 1.2207(2) 0.81083(11) -0.0137(3) 0.0578(5) Uani 1 1 d . . . H1 H 1.1433 0.7887 0.0323 0.069 Uiso 1 1 calc R . . C16 C 0.6254(2) 0.95796(12) 0.3959(3) 0.0600(6) Uani 1 1 d . . . H16A H 0.5717 1.0000 0.3546 0.072 Uiso 1 1 calc R . . H16B H 0.6481 0.9675 0.5040 0.072 Uiso 1 1 calc R . . C11 C 0.7718(2) 0.77359(12) 0.0935(3) 0.0629(6) Uani 1 1 d . . . H11A H 0.7551 0.7302 0.1555 0.094 Uiso 1 1 calc R . . H11B H 0.7953 0.7583 -0.0090 0.094 Uiso 1 1 calc R . . H11C H 0.6879 0.8039 0.0888 0.094 Uiso 1 1 calc R . . C5 C 1.3792(2) 0.91228(13) -0.0416(3) 0.0657(6) Uani 1 1 d . . . H5 H 1.4091 0.9603 -0.0160 0.079 Uiso 1 1 calc R . . C2 C 1.2960(2) 0.77066(14) -0.1197(3) 0.0693(6) Uani 1 1 d . . . H2 H 1.2672 0.7225 -0.1461 0.083 Uiso 1 1 calc R . . C3 C 1.4129(3) 0.80087(15) -0.1865(3) 0.0756(7) Uani 1 1 d . . . H3 H 1.4623 0.7738 -0.2592 0.091 Uiso 1 1 calc R . . C4 C 1.4562(3) 0.87139(16) -0.1453(3) 0.0772(8) Uani 1 1 d . . . H4 H 1.5373 0.8917 -0.1871 0.093 Uiso 1 1 calc R . . C17 C 0.5421(2) 0.88787(13) 0.3788(3) 0.0749(7) Uani 1 1 d . . . H17A H 0.5159 0.8805 0.2720 0.112 Uiso 1 1 calc R . . H17B H 0.4581 0.8914 0.4385 0.112 Uiso 1 1 calc R . . H17C H 0.5984 0.8464 0.4149 0.112 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 O2 0.0693(10) 0.0468(8) 0.0577(9) -0.0099(7) 0.0026(7) 0.0109(7) O3 0.0532(8) 0.0522(8) 0.0691(9) -0.0113(7) 0.0149(7) 0.0006(6) O4 0.0708(10) 0.0585(9) 0.0559(9) 0.0121(7) -0.0040(8) -0.0098(7) C10 0.0430(10) 0.0431(10) 0.0419(10) -0.0065(8) 0.0082(8) 0.0019(8) C9 0.0462(11) 0.0446(10) 0.0396(10) -0.0006(8) 0.0019(8) 0.0029(8) O1 0.0748(11) 0.0542(9) 0.0680(10) -0.0022(8) -0.0040(8) -0.0174(8) C8 0.0500(11) 0.0380(9) 0.0409(10) 0.0052(8) 0.0016(8) -0.0013(8) C7 0.0499(12) 0.0470(11) 0.0547(12) 0.0010(9) -0.0009(9) -0.0048(9) C13 0.0696(14) 0.0410(10) 0.0426(11) 0.0064(9) -0.0057(10) -0.0012(10) C12 0.0529(11) 0.0381(9) 0.0426(10) 0.0020(8) -0.0009(8) 0.0019(8) C15 0.0592(12) 0.0399(10) 0.0456(11) -0.0019(9) -0.0012(9) 0.0068(9) C14 0.0854(16) 0.0386(10) 0.0534(12) -0.0032(9) -0.0070(11) 0.0010(10) C6 0.0426(11) 0.0546(12) 0.0519(11) 0.0058(9) 0.0036(9) 0.0027(8) C1 0.0526(12) 0.0527(12) 0.0686(14) 0.0022(10) 0.0126(10) 0.0033(9) C16 0.0528(12) 0.0640(13) 0.0639(13) -0.0045(11) 0.0145(10) 0.0096(10) C11 0.0591(13) 0.0578(12) 0.0719(14) -0.0122(11) 0.0023(11) -0.0114(10) C5 0.0491(13) 0.0648(14) 0.0833(16) 0.0099(12) 0.0077(11) -0.0045(10) C2 0.0661(15) 0.0641(14) 0.0783(15) -0.0055(12) 0.0106(12) 0.0133(11) C3 0.0693(16) 0.0856(19) 0.0728(16) 0.0081(14) 0.0193(13) 0.0283(14) C4 0.0520(13) 0.0923(19) 0.0886(18) 0.0263(16) 0.0239(12) 0.0120(13) C17 0.0605(14) 0.0728(16) 0.0923(18) -0.0072(13) 0.0186(13) 0.0005(12) _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 O2 C15 1.336(2) . ? O2 C14 1.450(3) . ? O3 C15 1.313(2) . ? O3 C16 1.459(2) . ? O4 C10 1.208(2) . ? C10 C11 1.494(3) . ? C10 C9 1.505(2) . ? C9 C8 1.507(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? O1 C13 1.229(2) . ? C8 C7 1.339(3) . ? C8 C12 1.472(3) . ? C7 C6 1.474(3) . ? C7 H7 0.9300 . ? C13 C12 1.442(3) . ? C13 C14 1.511(3) . ? C12 C15 1.373(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C6 C5 1.394(3) . ? C6 C1 1.395(3) . ? C1 C2 1.378(3) . ? C1 H1 0.9300 . ? C16 C17 1.486(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C5 C4 1.380(3) . ? C5 H5 0.9300 . ? C2 C3 1.371(3) . ? C2 H2 0.9300 . ? C3 C4 1.371(4) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 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 C15 O2 C14 106.09(16) . . ? C15 O3 C16 118.87(16) . . ? O4 C10 C11 121.57(18) . . ? O4 C10 C9 122.06(16) . . ? C11 C10 C9 116.32(17) . . ? C8 C9 C10 116.14(15) . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C7 C8 C12 120.13(17) . . ? C7 C8 C9 123.03(17) . . ? C12 C8 C9 116.65(16) . . ? C8 C7 C6 129.42(18) . . ? C8 C7 H7 115.3 . . ? C6 C7 H7 115.3 . . ? O1 C13 C12 130.2(2) . . ? O1 C13 C14 123.32(18) . . ? C12 C13 C14 106.47(18) . . ? C15 C12 C13 104.80(17) . . ? C15 C12 C8 127.45(17) . . ? C13 C12 C8 127.72(18) . . ? O3 C15 O2 116.60(17) . . ? O3 C15 C12 126.44(17) . . ? O2 C15 C12 116.94(18) . . ? O2 C14 C13 105.39(15) . . ? O2 C14 H14A 110.7 . . ? C13 C14 H14A 110.7 . . ? O2 C14 H14B 110.7 . . ? C13 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? C5 C6 C1 116.30(19) . . ? C5 C6 C7 118.20(19) . . ? C1 C6 C7 125.50(18) . . ? C2 C1 C6 121.4(2) . . ? C2 C1 H1 119.3 . . ? C6 C1 H1 119.3 . . ? O3 C16 C17 106.89(17) . . ? O3 C16 H16A 110.3 . . ? C17 C16 H16A 110.3 . . ? O3 C16 H16B 110.3 . . ? C17 C16 H16B 110.3 . . ? H16A C16 H16B 108.6 . . ? 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 . . ? C4 C5 C6 122.1(2) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C3 C2 C1 120.7(2) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 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 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.126 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.031 data_4aa _database_code_depnum_ccdc_archive 'CCDC 913070' #TrackingRef 'web_deposit_cif_file_0_QiangWang_1354102642.4aa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (E)-ethyl 2-(2-(2-(2,4-dinitrophenyl)hydrazono)-2-phenylethyl)-2,5-dimethyl-7-phenylbenzo[d][1,3]dioxole-4-carboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H27 N4 O8' _chemical_formula_sum 'C32 H27 N4 O8' _chemical_formula_weight 595.58 _symmetry_space_group_name_Hall -p1 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.085(2) _cell_length_b 11.302(2) _cell_length_c 13.269(3) _cell_angle_alpha 80.76(3) _cell_angle_beta 78.81(3) _cell_angle_gamma 82.30(3) _cell_volume 1456.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3933 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 622 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9452 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 APEX CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14697 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5103 _reflns_number_gt 4057 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0772P)^2^+0.3862P] 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 5103 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0884 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.1756 _refine_ls_wR_factor_gt 0.1609 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 O6 O 0.30560(16) 0.69617(15) 0.34375(13) 0.0466(5) Uani 1 1 d . . . O5 O 0.18934(17) 0.63298(16) 0.50645(13) 0.0473(5) Uani 1 1 d . . . N4 N 0.1535(2) 0.91895(19) 0.53675(16) 0.0464(5) Uani 1 1 d . . . O7 O 0.5392(2) 0.72483(19) 0.21687(15) 0.0624(6) Uani 1 1 d . . . N3 N 0.0682(2) 0.8525(2) 0.61184(16) 0.0500(6) Uani 1 1 d . . . C7 C 0.1658(2) 0.8990(2) 0.44177(19) 0.0422(6) Uani 1 1 d . . . C26 C 0.5252(3) 0.7096(2) 0.3954(2) 0.0446(6) Uani 1 1 d . . . C4 C 0.0695(3) 0.8613(2) 0.71233(19) 0.0448(6) Uani 1 1 d . . . C24 C 0.3230(2) 0.6453(2) 0.5119(2) 0.0420(6) Uani 1 1 d . . . C25 C 0.3911(3) 0.6836(2) 0.41459(19) 0.0416(6) Uani 1 1 d . . . C8 C 0.2656(3) 0.9675(2) 0.36556(19) 0.0426(6) Uani 1 1 d . . . C14 C 0.0912(2) 0.8100(2) 0.40609(19) 0.0445(6) Uani 1 1 d . . . H14A H 0.0720 0.8418 0.3375 0.053 Uiso 1 1 calc R . . H14B H 0.0049 0.8021 0.4526 0.053 Uiso 1 1 calc R . . N2 N -0.1017(2) 0.7120(2) 0.7789(2) 0.0583(6) Uani 1 1 d . . . O4 O -0.1057(2) 0.6979(2) 0.68877(17) 0.0759(7) Uani 1 1 d . . . C23 C 0.3827(3) 0.6257(2) 0.5991(2) 0.0449(6) Uani 1 1 d . . . C27 C 0.5906(3) 0.6905(2) 0.4829(2) 0.0509(7) Uani 1 1 d . . . C3 C -0.0088(3) 0.7909(2) 0.7956(2) 0.0476(6) Uani 1 1 d . . . O8 O 0.6857(2) 0.8201(2) 0.27148(18) 0.0808(7) Uani 1 1 d . . . C5 C 0.1491(3) 0.9404(2) 0.7398(2) 0.0528(7) Uani 1 1 d . . . H5 H 0.1973 0.9916 0.6878 0.063 Uiso 1 1 calc R . . C28 C 0.5200(3) 0.6485(2) 0.5788(2) 0.0526(7) Uani 1 1 d . . . H28 H 0.5664 0.6342 0.6344 0.063 Uiso 1 1 calc R . . O3 O -0.1737(3) 0.6620(2) 0.85311(18) 0.0867(8) Uani 1 1 d . . . C13 C 0.2644(3) 0.9835(2) 0.2598(2) 0.0526(7) Uani 1 1 d . . . H13 H 0.1980 0.9521 0.2353 0.063 Uiso 1 1 calc R . . C6 C 0.1571(3) 0.9440(3) 0.8407(2) 0.0567(7) Uani 1 1 d . . . H6 H 0.2098 0.9975 0.8568 0.068 Uiso 1 1 calc R . . C1 C 0.0868(3) 0.8678(3) 0.9190(2) 0.0548(7) Uani 1 1 d . . . C2 C 0.0023(3) 0.7936(2) 0.8974(2) 0.0539(7) Uani 1 1 d . . . H2 H -0.0474 0.7453 0.9510 0.065 Uiso 1 1 calc R . . C30 C 0.5935(3) 0.7578(2) 0.2904(2) 0.0516(7) Uani 1 1 d . . . C9 C 0.3679(3) 1.0143(2) 0.3992(2) 0.0519(7) Uani 1 1 d . . . H9 H 0.3714 1.0038 0.4696 0.062 Uiso 1 1 calc R . . C10 C 0.4634(3) 1.0757(3) 0.3300(2) 0.0597(8) Uani 1 1 d . . . H10 H 0.5307 1.1067 0.3539 0.072 Uiso 1 1 calc R . . C17 C 0.2026(3) 0.5189(2) 0.7237(2) 0.0550(7) Uani 1 1 d . . . H17 H 0.1719 0.4979 0.6679 0.066 Uiso 1 1 calc R . . C22 C 0.3112(3) 0.5873(2) 0.7055(2) 0.0488(7) Uani 1 1 d . . . C12 C 0.3603(3) 1.0453(3) 0.1908(2) 0.0627(8) Uani 1 1 d . . . H12 H 0.3579 1.0560 0.1202 0.075 Uiso 1 1 calc R . . C11 C 0.4600(3) 1.0915(3) 0.2262(2) 0.0635(8) Uani 1 1 d . . . H11 H 0.5247 1.1332 0.1794 0.076 Uiso 1 1 calc R . . C19 C 0.1817(4) 0.5125(3) 0.9069(2) 0.0718(9) Uani 1 1 d . . . H19 H 0.1387 0.4872 0.9740 0.086 Uiso 1 1 calc R . . C21 C 0.3518(3) 0.6182(3) 0.7917(2) 0.0637(8) Uani 1 1 d . . . H21 H 0.4236 0.6649 0.7822 0.076 Uiso 1 1 calc R . . N1 N 0.1028(3) 0.8650(3) 1.0263(2) 0.0758(8) Uani 1 1 d . . . O2 O 0.0425(3) 0.7963(3) 1.09373(19) 0.1106(10) Uani 1 1 d . . . C18 C 0.1392(3) 0.4814(3) 0.8236(2) 0.0688(9) Uani 1 1 d . . . H18 H 0.0671 0.4348 0.8344 0.083 Uiso 1 1 calc R . . C29 C 0.7372(3) 0.7144(3) 0.4741(3) 0.0714(9) Uani 1 1 d . . . H29A H 0.7420 0.7997 0.4669 0.107 Uiso 1 1 calc R . . H29B H 0.7913 0.6829 0.4145 0.107 Uiso 1 1 calc R . . H29C H 0.7709 0.6757 0.5354 0.107 Uiso 1 1 calc R . . C31 C 0.5917(3) 0.7690(3) 0.1101(2) 0.0728(9) Uani 1 1 d . . . H31A H 0.6867 0.7388 0.0918 0.087 Uiso 1 1 calc R . . H31B H 0.5839 0.8564 0.0992 0.087 Uiso 1 1 calc R . . C20 C 0.2871(4) 0.5806(3) 0.8908(2) 0.0736(9) Uani 1 1 d . . . H20 H 0.3158 0.6020 0.9473 0.088 Uiso 1 1 calc R . . O1 O 0.1771(3) 0.9337(3) 1.04352(19) 0.1020(9) Uani 1 1 d . . . C32 C 0.5082(5) 0.7240(4) 0.0466(3) 0.1042(14) Uani 1 1 d . . . H32A H 0.5024 0.6393 0.0681 0.156 Uiso 1 1 calc R . . H32B H 0.5496 0.7372 -0.0253 0.156 Uiso 1 1 calc R . . H32C H 0.4186 0.7664 0.0558 0.156 Uiso 1 1 calc R . . C15 C 0.1708(2) 0.6848(2) 0.40248(19) 0.0442(6) Uani 1 1 d . . . C16 C 0.1036(3) 0.6007(3) 0.3564(2) 0.0596(8) Uani 1 1 d . . . H16A H 0.1615 0.5265 0.3511 0.089 Uiso 1 1 calc R . . H16B H 0.0881 0.6372 0.2886 0.089 Uiso 1 1 calc R . . H16C H 0.0184 0.5848 0.4000 0.089 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 O6 0.0394(10) 0.0589(11) 0.0428(10) -0.0037(8) -0.0097(8) -0.0103(8) O5 0.0422(10) 0.0560(11) 0.0449(10) 0.0034(8) -0.0121(8) -0.0158(8) N4 0.0486(13) 0.0488(13) 0.0402(12) -0.0027(10) -0.0026(10) -0.0115(10) O7 0.0550(12) 0.0768(14) 0.0531(12) -0.0031(10) -0.0017(10) -0.0171(10) N3 0.0544(14) 0.0581(14) 0.0362(12) -0.0005(10) -0.0044(10) -0.0137(11) C7 0.0423(14) 0.0417(14) 0.0417(15) -0.0024(11) -0.0086(11) -0.0035(11) C26 0.0383(14) 0.0400(14) 0.0573(16) -0.0116(12) -0.0095(12) -0.0033(11) C4 0.0440(15) 0.0473(15) 0.0422(15) -0.0045(12) -0.0065(11) -0.0052(12) C24 0.0385(14) 0.0386(13) 0.0516(16) -0.0043(11) -0.0142(12) -0.0068(11) C25 0.0444(14) 0.0378(14) 0.0455(15) -0.0067(11) -0.0139(12) -0.0054(11) C8 0.0466(15) 0.0392(14) 0.0409(14) -0.0037(11) -0.0071(11) -0.0039(11) C14 0.0377(14) 0.0556(16) 0.0420(14) -0.0017(12) -0.0110(11) -0.0117(12) N2 0.0626(16) 0.0565(15) 0.0536(15) 0.0012(12) -0.0052(12) -0.0160(12) O4 0.0906(17) 0.0873(16) 0.0588(14) -0.0072(12) -0.0139(12) -0.0440(13) C23 0.0532(16) 0.0367(14) 0.0472(15) -0.0044(11) -0.0161(12) -0.0041(12) C27 0.0393(15) 0.0473(15) 0.0707(19) -0.0155(14) -0.0161(14) -0.0031(12) C3 0.0491(16) 0.0490(15) 0.0442(15) -0.0061(12) -0.0053(12) -0.0076(12) O8 0.0694(15) 0.0845(16) 0.0898(17) -0.0082(13) 0.0007(12) -0.0393(13) C5 0.0562(17) 0.0535(16) 0.0492(16) -0.0093(13) -0.0037(13) -0.0133(13) C28 0.0529(17) 0.0511(16) 0.0609(18) -0.0098(14) -0.0274(14) -0.0028(13) O3 0.0907(17) 0.0997(18) 0.0672(15) 0.0135(13) -0.0002(13) -0.0514(15) C13 0.0634(18) 0.0542(17) 0.0424(15) -0.0034(13) -0.0123(13) -0.0134(14) C6 0.0571(18) 0.0611(18) 0.0560(18) -0.0172(14) -0.0105(14) -0.0095(14) C1 0.0648(19) 0.0583(17) 0.0423(15) -0.0119(13) -0.0128(14) 0.0006(14) C2 0.0594(18) 0.0530(17) 0.0435(16) -0.0014(13) -0.0017(13) -0.0026(13) C30 0.0399(15) 0.0471(16) 0.0662(19) -0.0092(14) -0.0053(13) -0.0035(12) C9 0.0569(17) 0.0547(17) 0.0462(15) -0.0040(13) -0.0110(13) -0.0145(13) C10 0.0608(19) 0.0581(18) 0.0637(19) -0.0025(15) -0.0146(15) -0.0209(15) C17 0.0670(19) 0.0515(16) 0.0482(16) -0.0003(13) -0.0151(14) -0.0130(14) C22 0.0574(17) 0.0398(14) 0.0521(16) -0.0023(12) -0.0220(13) -0.0025(12) C12 0.082(2) 0.0587(18) 0.0438(16) 0.0035(14) -0.0063(15) -0.0156(16) C11 0.070(2) 0.0556(18) 0.062(2) 0.0043(15) -0.0029(16) -0.0220(15) C19 0.089(3) 0.069(2) 0.0507(19) 0.0097(16) -0.0116(17) -0.0071(19) C21 0.080(2) 0.0607(19) 0.0547(18) -0.0046(15) -0.0227(16) -0.0121(16) N1 0.095(2) 0.084(2) 0.0496(17) -0.0197(16) -0.0166(16) 0.0060(17) O2 0.160(3) 0.124(2) 0.0467(15) 0.0037(15) -0.0181(17) -0.030(2) C18 0.078(2) 0.064(2) 0.063(2) 0.0044(16) -0.0136(17) -0.0179(17) C29 0.0429(17) 0.088(2) 0.090(2) -0.0235(19) -0.0170(16) -0.0097(16) C31 0.071(2) 0.080(2) 0.0546(19) 0.0071(16) 0.0076(16) -0.0079(18) C20 0.099(3) 0.075(2) 0.0513(19) -0.0060(16) -0.0259(18) -0.010(2) O1 0.129(2) 0.125(2) 0.0685(17) -0.0343(15) -0.0363(16) -0.0187(19) C32 0.121(4) 0.128(4) 0.061(2) 0.004(2) -0.021(2) -0.018(3) C15 0.0397(14) 0.0550(16) 0.0402(14) -0.0007(12) -0.0114(11) -0.0143(12) C16 0.0613(19) 0.0656(19) 0.0610(18) -0.0122(15) -0.0194(15) -0.0223(15) _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 O6 C25 1.374(3) . ? O6 C15 1.441(3) . ? O5 C24 1.390(3) . ? O5 C15 1.447(3) . ? N4 C7 1.295(3) . ? N4 N3 1.377(3) . ? O7 C30 1.330(3) . ? O7 C31 1.445(3) . ? N3 C4 1.356(3) . ? C7 C8 1.483(3) . ? C7 C14 1.515(3) . ? C26 C25 1.388(3) . ? C26 C27 1.417(4) . ? C26 C30 1.482(4) . ? C4 C5 1.410(4) . ? C4 C3 1.423(4) . ? C24 C25 1.372(4) . ? C24 C23 1.379(3) . ? C8 C13 1.388(3) . ? C8 C9 1.394(4) . ? C14 C15 1.533(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N2 O3 1.213(3) . ? N2 O4 1.240(3) . ? N2 C3 1.445(3) . ? C23 C28 1.409(4) . ? C23 C22 1.480(4) . ? C27 C28 1.378(4) . ? C27 C29 1.517(4) . ? C3 C2 1.383(4) . ? O8 C30 1.205(3) . ? C5 C6 1.363(4) . ? C5 H5 0.9300 . ? C28 H28 0.9300 . ? C13 C12 1.376(4) . ? C13 H13 0.9300 . ? C6 C1 1.384(4) . ? C6 H6 0.9300 . ? C1 C2 1.370(4) . ? C1 N1 1.458(4) . ? C2 H2 0.9300 . ? C9 C10 1.372(4) . ? C9 H9 0.9300 . ? C10 C11 1.368(4) . ? C10 H10 0.9300 . ? C17 C18 1.382(4) . ? C17 C22 1.387(4) . ? C17 H17 0.9300 . ? C22 C21 1.395(4) . ? C12 C11 1.381(4) . ? C12 H12 0.9300 . ? C11 H11 0.9300 . ? C19 C20 1.358(5) . ? C19 C18 1.370(4) . ? C19 H19 0.9300 . ? C21 C20 1.377(4) . ? C21 H21 0.9300 . ? N1 O2 1.211(4) . ? N1 O1 1.223(4) . ? C18 H18 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C31 C32 1.486(5) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C20 H20 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C15 C16 1.502(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 C25 O6 C15 106.61(18) . . ? C24 O5 C15 106.05(18) . . ? C7 N4 N3 117.7(2) . . ? C30 O7 C31 117.9(2) . . ? C4 N3 N4 117.6(2) . . ? N4 C7 C8 115.2(2) . . ? N4 C7 C14 125.1(2) . . ? C8 C7 C14 119.7(2) . . ? C25 C26 C27 115.8(2) . . ? C25 C26 C30 121.8(2) . . ? C27 C26 C30 122.4(2) . . ? N3 C4 C5 121.7(2) . . ? N3 C4 C3 121.8(2) . . ? C5 C4 C3 116.5(2) . . ? C25 C24 C23 123.1(2) . . ? C25 C24 O5 109.3(2) . . ? C23 C24 O5 127.6(2) . . ? O6 C25 C24 109.9(2) . . ? O6 C25 C26 127.0(2) . . ? C24 C25 C26 123.1(2) . . ? C13 C8 C9 118.0(2) . . ? C13 C8 C7 122.1(2) . . ? C9 C8 C7 119.9(2) . . ? C7 C14 C15 113.5(2) . . ? C7 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C7 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? O3 N2 O4 122.0(3) . . ? O3 N2 C3 119.2(3) . . ? O4 N2 C3 118.9(2) . . ? C24 C23 C28 113.7(2) . . ? C24 C23 C22 124.4(2) . . ? C28 C23 C22 121.8(2) . . ? C28 C27 C26 119.4(2) . . ? C28 C27 C29 118.7(3) . . ? C26 C27 C29 121.9(3) . . ? C2 C3 C4 121.0(3) . . ? C2 C3 N2 116.6(2) . . ? C4 C3 N2 122.4(2) . . ? C6 C5 C4 121.8(3) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C27 C28 C23 124.9(2) . . ? C27 C28 H28 117.5 . . ? C23 C28 H28 117.5 . . ? C12 C13 C8 120.7(3) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C5 C6 C1 119.8(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C2 C1 C6 120.9(3) . . ? C2 C1 N1 119.0(3) . . ? C6 C1 N1 120.1(3) . . ? C1 C2 C3 119.7(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? O8 C30 O7 122.9(3) . . ? O8 C30 C26 125.7(3) . . ? O7 C30 C26 111.5(2) . . ? C10 C9 C8 121.1(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C18 C17 C22 120.9(3) . . ? C18 C17 H17 119.6 . . ? C22 C17 H17 119.6 . . ? C17 C22 C21 117.3(3) . . ? C17 C22 C23 121.7(2) . . ? C21 C22 C23 121.0(3) . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C10 C11 C12 119.9(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C20 C19 C18 119.6(3) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C20 C21 C22 121.0(3) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? O2 N1 O1 123.1(3) . . ? O2 N1 C1 119.3(3) . . ? O1 N1 C1 117.6(3) . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O7 C31 C32 106.1(3) . . ? O7 C31 H31A 110.5 . . ? C32 C31 H31A 110.5 . . ? O7 C31 H31B 110.5 . . ? C32 C31 H31B 110.5 . . ? H31A C31 H31B 108.7 . . ? C19 C20 C21 120.6(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? 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 . . ? O6 C15 O5 105.63(18) . . ? O6 C15 C16 109.0(2) . . ? O5 C15 C16 110.0(2) . . ? O6 C15 C14 109.71(19) . . ? O5 C15 C14 108.9(2) . . ? C16 C15 C14 113.4(2) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.479 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.038