# Electronic Supplementary Material (ESI) for Chemical Communications # 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_7a _database_code_depnum_ccdc_archive 'CCDC 923923' #TrackingRef '7a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 N2 O4' _chemical_formula_sum 'C26 H26 N2 O4' _chemical_formula_weight 430.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5876(2) _cell_length_b 20.5244(3) _cell_length_c 12.2009(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.667(2) _cell_angle_gamma 90.00 _cell_volume 2135.93(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123.00(10) _cell_measurement_reflns_used 3749 _cell_measurement_theta_min 3.6443 _cell_measurement_theta_max 74.2165 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.0853 _exptl_crystal_size_mid 0.0678 _exptl_crystal_size_min 0.0314 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.733 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93471 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123.00(10) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.2640 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8314 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 74.38 _reflns_number_total 4185 _reflns_number_gt 3330 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SIR-2004 (Altomare, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2006)' _computing_publication_material 'SHELXL-97(Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0572P)^2^+0.5719P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4185 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.16794(13) 0.06992(6) 0.10582(9) 0.0272(3) Uani 1 1 d . . . O2 O 0.03830(16) 0.07016(6) -0.06582(10) 0.0330(3) Uani 1 1 d . . . O3 O 0.15985(16) 0.24120(7) 0.69743(10) 0.0412(3) Uani 1 1 d . . . N2 N -0.02483(18) 0.19628(7) 0.57802(11) 0.0275(3) Uani 1 1 d . . . N1 N -0.08037(16) 0.10687(6) 0.08119(11) 0.0238(3) Uani 1 1 d . . . C1 C -0.2183(2) 0.13074(7) 0.01987(13) 0.0245(3) Uani 1 1 d . . . C6 C -0.31449(19) 0.15621(8) 0.09508(13) 0.0243(3) Uani 1 1 d . . . C24 C -0.3166(2) -0.03051(8) 0.52052(14) 0.0281(4) Uani 1 1 d . . . H24 H -0.3593 -0.0357 0.5866 0.034 Uiso 1 1 calc R . . O4 O 0.15381(17) 0.26812(9) 0.51899(12) 0.0499(4) Uani 1 1 d . . . C7 C -0.23383(19) 0.14660(7) 0.20405(13) 0.0229(3) Uani 1 1 d . . . C8 C -0.09446(19) 0.11726(7) 0.19494(13) 0.0228(3) Uani 1 1 d . . . C25 C -0.2267(2) 0.02406(8) 0.50511(14) 0.0263(3) Uani 1 1 d . . . H25 H -0.2100 0.0547 0.5614 0.032 Uiso 1 1 calc R . . C10 C -0.06065(19) 0.09509(8) 0.39734(13) 0.0228(3) Uani 1 1 d . . . H10 H 0.0213 0.0955 0.4603 0.027 Uiso 1 1 calc R . . C2 C -0.2635(2) 0.13197(8) -0.09339(14) 0.0292(4) Uani 1 1 d . . . H2 H -0.2001 0.1146 -0.1429 0.035 Uiso 1 1 calc R . . C16 C -0.1400(2) 0.19996(8) 0.48355(13) 0.0258(3) Uani 1 1 d . . . H16 H -0.2053 0.2363 0.4770 0.031 Uiso 1 1 calc R . . C21 C -0.1900(2) -0.01244(8) 0.32429(14) 0.0276(4) Uani 1 1 d . . . H21 H -0.1491 -0.0070 0.2576 0.033 Uiso 1 1 calc R . . C5 C -0.4594(2) 0.18420(8) 0.05677(14) 0.0280(4) Uani 1 1 d . . . H5 H -0.5242 0.2010 0.1059 0.034 Uiso 1 1 calc R . . C3 C -0.4071(2) 0.16018(9) -0.12946(14) 0.0321(4) Uani 1 1 d . . . H3 H -0.4399 0.1618 -0.2048 0.039 Uiso 1 1 calc R . . C17 C 0.0993(2) 0.23784(10) 0.58991(14) 0.0329(4) Uani 1 1 d . . . C23 C -0.3440(2) -0.07767(8) 0.43863(15) 0.0281(4) Uani 1 1 d . . . C12 C -0.29114(19) 0.16299(8) 0.31202(13) 0.0248(3) Uani 1 1 d . . . H12A H -0.3774 0.1344 0.3244 0.030 Uiso 1 1 calc R . . H12B H -0.3291 0.2075 0.3102 0.030 Uiso 1 1 calc R . . C9 C 0.02081(19) 0.09736(8) 0.29075(13) 0.0243(3) Uani 1 1 d . . . H9B H 0.1069 0.1282 0.2998 0.029 Uiso 1 1 calc R . . H9A H 0.0633 0.0548 0.2768 0.029 Uiso 1 1 calc R . . C13 C 0.0443(2) 0.08103(8) 0.03200(14) 0.0257(3) Uani 1 1 d . . . C4 C -0.5040(2) 0.18627(8) -0.05604(15) 0.0308(4) Uani 1 1 d . . . H4 H -0.5992 0.2052 -0.0831 0.037 Uiso 1 1 calc R . . C22 C -0.2807(2) -0.06724(8) 0.34071(15) 0.0302(4) Uani 1 1 d . . . H22 H -0.2991 -0.0977 0.2842 0.036 Uiso 1 1 calc R . . C14 C 0.3027(2) 0.04167(8) 0.06151(15) 0.0294(4) Uani 1 1 d . . . H14B H 0.3457 0.0722 0.0124 0.035 Uiso 1 1 calc R . . H14A H 0.2727 0.0022 0.0206 0.035 Uiso 1 1 calc R . . C11 C -0.16025(18) 0.15523(8) 0.40474(13) 0.0226(3) Uani 1 1 d . . . C20 C -0.16037(19) 0.03423(8) 0.40701(13) 0.0234(3) Uani 1 1 d . . . C18 C 0.0646(2) 0.20331(10) 0.76398(14) 0.0366(4) Uani 1 1 d . . . H18B H 0.0293 0.2299 0.8221 0.044 Uiso 1 1 calc R . . H18A H 0.1233 0.1665 0.7973 0.044 Uiso 1 1 calc R . . C26 C -0.4376(2) -0.13793(9) 0.45689(18) 0.0393(4) Uani 1 1 d . . . H26A H -0.5465 -0.1267 0.4546 0.059 Uiso 1 1 calc R . . H26B H -0.4014 -0.1563 0.5276 0.059 Uiso 1 1 calc R . . H26C H -0.4247 -0.1692 0.4001 0.059 Uiso 1 1 calc R . . C19 C -0.0733(3) 0.18027(10) 0.68488(14) 0.0389(4) Uani 1 1 d . . . H19A H -0.0899 0.1338 0.6919 0.047 Uiso 1 1 calc R . . H19B H -0.1686 0.2032 0.6970 0.047 Uiso 1 1 calc R . . C15 C 0.4215(2) 0.02652(10) 0.15847(16) 0.0366(4) Uani 1 1 d . . . H15B H 0.4479 0.0657 0.1993 0.055 Uiso 1 1 calc R . . H15A H 0.5141 0.0088 0.1327 0.055 Uiso 1 1 calc R . . H15C H 0.3785 -0.0046 0.2053 0.055 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 0.0267(6) 0.0275(6) 0.0279(6) -0.0028(5) 0.0051(5) 0.0030(5) O2 0.0405(7) 0.0349(7) 0.0240(6) -0.0022(5) 0.0058(5) 0.0020(5) O3 0.0423(8) 0.0507(8) 0.0283(7) 0.0001(6) -0.0063(6) -0.0072(6) N2 0.0338(8) 0.0273(7) 0.0207(7) -0.0016(6) 0.0004(6) 0.0001(6) N1 0.0263(7) 0.0222(6) 0.0224(7) -0.0001(5) 0.0012(5) 0.0015(5) C1 0.0303(8) 0.0177(7) 0.0244(8) 0.0017(6) -0.0017(6) -0.0028(6) C6 0.0278(8) 0.0193(7) 0.0248(8) 0.0019(6) -0.0019(6) -0.0030(6) C24 0.0293(9) 0.0274(8) 0.0281(8) 0.0042(7) 0.0053(7) 0.0032(7) O4 0.0380(8) 0.0730(11) 0.0375(8) 0.0144(7) -0.0003(6) -0.0151(7) C7 0.0251(8) 0.0195(7) 0.0234(8) 0.0012(6) 0.0006(6) -0.0001(6) C8 0.0267(8) 0.0200(7) 0.0213(8) 0.0009(6) 0.0011(6) -0.0019(6) C25 0.0290(9) 0.0243(8) 0.0248(8) -0.0023(7) 0.0001(6) 0.0031(6) C10 0.0249(8) 0.0223(7) 0.0203(7) -0.0001(6) -0.0011(6) 0.0023(6) C2 0.0375(10) 0.0261(8) 0.0236(8) 0.0013(7) 0.0016(7) -0.0041(7) C16 0.0299(9) 0.0225(8) 0.0244(8) 0.0016(6) 0.0006(7) 0.0023(6) C21 0.0326(9) 0.0247(8) 0.0256(8) 0.0002(7) 0.0039(7) -0.0003(7) C5 0.0283(9) 0.0223(8) 0.0325(9) 0.0023(7) -0.0004(7) -0.0016(6) C3 0.0391(10) 0.0291(8) 0.0258(8) 0.0043(7) -0.0058(7) -0.0091(7) C17 0.0308(9) 0.0409(10) 0.0260(8) 0.0023(8) -0.0005(7) 0.0006(8) C23 0.0254(8) 0.0233(8) 0.0346(9) 0.0027(7) -0.0004(7) 0.0018(6) C12 0.0240(8) 0.0240(8) 0.0259(8) -0.0009(6) 0.0001(6) 0.0028(6) C9 0.0240(8) 0.0242(8) 0.0244(8) 0.0003(6) 0.0017(6) 0.0022(6) C13 0.0313(9) 0.0197(7) 0.0265(8) 0.0003(6) 0.0047(7) -0.0018(6) C4 0.0299(9) 0.0260(8) 0.0341(9) 0.0063(7) -0.0061(7) -0.0031(7) C22 0.0345(9) 0.0240(8) 0.0307(9) -0.0057(7) -0.0018(7) -0.0001(7) C14 0.0283(8) 0.0274(8) 0.0338(9) -0.0035(7) 0.0093(7) 0.0001(7) C11 0.0242(8) 0.0210(7) 0.0228(8) 0.0018(6) 0.0034(6) 0.0000(6) C20 0.0232(8) 0.0215(7) 0.0246(8) 0.0018(6) -0.0013(6) 0.0043(6) C18 0.0478(11) 0.0392(10) 0.0226(9) -0.0006(8) 0.0033(8) 0.0028(8) C26 0.0411(11) 0.0313(9) 0.0461(11) 0.0014(8) 0.0075(9) -0.0057(8) C19 0.0502(12) 0.0427(11) 0.0237(9) 0.0019(8) 0.0039(8) -0.0107(9) C15 0.0297(9) 0.0383(10) 0.0418(10) -0.0060(8) 0.0043(8) 0.0025(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C13 1.330(2) . ? O1 C14 1.454(2) . ? O2 C13 1.209(2) . ? O3 C17 1.356(2) . ? O3 C18 1.445(2) . ? N2 C17 1.360(2) . ? N2 C16 1.431(2) . ? N2 C19 1.452(2) . ? N1 C13 1.391(2) . ? N1 C1 1.413(2) . ? N1 C8 1.423(2) . ? C1 C2 1.392(2) . ? C1 C6 1.405(2) . ? C6 C5 1.401(2) . ? C6 C7 1.440(2) . ? C24 C25 1.386(2) . ? C24 C23 1.391(2) . ? C24 H24 0.9300 . ? O4 C17 1.203(2) . ? C7 C8 1.356(2) . ? C7 C12 1.497(2) . ? C8 C9 1.498(2) . ? C25 C20 1.400(2) . ? C25 H25 0.9300 . ? C10 C11 1.510(2) . ? C10 C20 1.527(2) . ? C10 C9 1.547(2) . ? C10 H10 0.9800 . ? C2 C3 1.387(3) . ? C2 H2 0.9300 . ? C16 C11 1.326(2) . ? C16 H16 0.9300 . ? C21 C20 1.393(2) . ? C21 C22 1.395(2) . ? C21 H21 0.9300 . ? C5 C4 1.386(2) . ? C5 H5 0.9300 . ? C3 C4 1.398(3) . ? C3 H3 0.9300 . ? C23 C22 1.386(3) . ? C23 C26 1.506(2) . ? C12 C11 1.508(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? C4 H4 0.9300 . ? C22 H22 0.9300 . ? C14 C15 1.502(3) . ? C14 H14B 0.9700 . ? C14 H14A 0.9700 . ? C18 C19 1.514(3) . ? C18 H18B 0.9700 . ? C18 H18A 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C15 H15B 0.9600 . ? C15 H15A 0.9600 . ? C15 H15C 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 C13 O1 C14 115.10(13) . . ? C17 O3 C18 109.74(14) . . ? C17 N2 C16 120.85(14) . . ? C17 N2 C19 110.44(14) . . ? C16 N2 C19 119.46(15) . . ? C13 N1 C1 122.90(14) . . ? C13 N1 C8 129.38(14) . . ? C1 N1 C8 107.67(13) . . ? C2 C1 C6 121.61(15) . . ? C2 C1 N1 130.72(16) . . ? C6 C1 N1 107.67(13) . . ? C5 C6 C1 120.11(15) . . ? C5 C6 C7 132.68(16) . . ? C1 C6 C7 107.20(14) . . ? C25 C24 C23 121.01(16) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C8 C7 C6 108.65(14) . . ? C8 C7 C12 123.74(14) . . ? C6 C7 C12 127.58(14) . . ? C7 C8 N1 108.80(14) . . ? C7 C8 C9 124.52(15) . . ? N1 C8 C9 126.64(14) . . ? C24 C25 C20 121.68(15) . . ? C24 C25 H25 119.2 . . ? C20 C25 H25 119.2 . . ? C11 C10 C20 109.72(13) . . ? C11 C10 C9 109.88(13) . . ? C20 C10 C9 113.70(13) . . ? C11 C10 H10 107.8 . . ? C20 C10 H10 107.8 . . ? C9 C10 H10 107.8 . . ? C3 C2 C1 117.28(17) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C11 C16 N2 124.57(15) . . ? C11 C16 H16 117.7 . . ? N2 C16 H16 117.7 . . ? C20 C21 C22 120.55(16) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C4 C5 C6 118.45(17) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C2 C3 C4 122.00(16) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? O4 C17 O3 122.14(18) . . ? O4 C17 N2 127.79(17) . . ? O3 C17 N2 110.07(15) . . ? C22 C23 C24 117.47(16) . . ? C22 C23 C26 121.62(16) . . ? C24 C23 C26 120.91(17) . . ? C7 C12 C11 110.12(13) . . ? C7 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? C7 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.2 . . ? C8 C9 C10 109.99(13) . . ? C8 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? H9B C9 H9A 108.2 . . ? O2 C13 O1 125.14(16) . . ? O2 C13 N1 123.33(16) . . ? O1 C13 N1 111.53(14) . . ? C5 C4 C3 120.54(16) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C23 C22 C21 121.98(16) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? O1 C14 C15 106.68(14) . . ? O1 C14 H14B 110.4 . . ? C15 C14 H14B 110.4 . . ? O1 C14 H14A 110.4 . . ? C15 C14 H14A 110.4 . . ? H14B C14 H14A 108.6 . . ? C16 C11 C12 119.62(15) . . ? C16 C11 C10 125.57(15) . . ? C12 C11 C10 114.80(13) . . ? C21 C20 C25 117.29(15) . . ? C21 C20 C10 124.30(15) . . ? C25 C20 C10 118.41(14) . . ? O3 C18 C19 105.19(14) . . ? O3 C18 H18B 110.7 . . ? C19 C18 H18B 110.7 . . ? O3 C18 H18A 110.7 . . ? C19 C18 H18A 110.7 . . ? H18B C18 H18A 108.8 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N2 C19 C18 102.54(16) . . ? N2 C19 H19A 111.3 . . ? C18 C19 H19A 111.3 . . ? N2 C19 H19B 111.3 . . ? C18 C19 H19B 111.3 . . ? H19A C19 H19B 109.2 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15A 109.5 . . ? H15B C15 H15A 109.5 . . ? C14 C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H15A C15 H15C 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 C13 N1 C1 C2 2.9(3) . . . . ? C8 N1 C1 C2 -179.56(16) . . . . ? C13 N1 C1 C6 -176.80(14) . . . . ? C8 N1 C1 C6 0.78(17) . . . . ? C2 C1 C6 C5 -0.5(2) . . . . ? N1 C1 C6 C5 179.17(14) . . . . ? C2 C1 C6 C7 179.46(14) . . . . ? N1 C1 C6 C7 -0.84(17) . . . . ? C5 C6 C7 C8 -179.41(17) . . . . ? C1 C6 C7 C8 0.60(18) . . . . ? C5 C6 C7 C12 2.7(3) . . . . ? C1 C6 C7 C12 -177.27(15) . . . . ? C6 C7 C8 N1 -0.11(18) . . . . ? C12 C7 C8 N1 177.86(14) . . . . ? C6 C7 C8 C9 -178.04(14) . . . . ? C12 C7 C8 C9 -0.1(3) . . . . ? C13 N1 C8 C7 176.96(15) . . . . ? C1 N1 C8 C7 -0.41(17) . . . . ? C13 N1 C8 C9 -5.2(3) . . . . ? C1 N1 C8 C9 177.46(15) . . . . ? C23 C24 C25 C20 0.3(3) . . . . ? C6 C1 C2 C3 0.8(2) . . . . ? N1 C1 C2 C3 -178.82(16) . . . . ? C17 N2 C16 C11 111.2(2) . . . . ? C19 N2 C16 C11 -105.2(2) . . . . ? C1 C6 C5 C4 -0.3(2) . . . . ? C7 C6 C5 C4 179.71(17) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C18 O3 C17 O4 176.23(19) . . . . ? C18 O3 C17 N2 -4.3(2) . . . . ? C16 N2 C17 O4 -21.7(3) . . . . ? C19 N2 C17 O4 -168.2(2) . . . . ? C16 N2 C17 O3 158.91(15) . . . . ? C19 N2 C17 O3 12.4(2) . . . . ? C25 C24 C23 C22 -1.3(3) . . . . ? C25 C24 C23 C26 178.12(16) . . . . ? C8 C7 C12 C11 11.7(2) . . . . ? C6 C7 C12 C11 -170.75(15) . . . . ? C7 C8 C9 C10 17.4(2) . . . . ? N1 C8 C9 C10 -160.12(14) . . . . ? C11 C10 C9 C8 -45.46(17) . . . . ? C20 C10 C9 C8 77.94(16) . . . . ? C14 O1 C13 O2 -0.9(2) . . . . ? C14 O1 C13 N1 178.87(13) . . . . ? C1 N1 C13 O2 -8.5(2) . . . . ? C8 N1 C13 O2 174.45(15) . . . . ? C1 N1 C13 O1 171.73(13) . . . . ? C8 N1 C13 O1 -5.3(2) . . . . ? C6 C5 C4 C3 0.8(2) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C24 C23 C22 C21 1.2(3) . . . . ? C26 C23 C22 C21 -178.15(17) . . . . ? C20 C21 C22 C23 -0.2(3) . . . . ? C13 O1 C14 C15 -174.12(14) . . . . ? N2 C16 C11 C12 176.96(15) . . . . ? N2 C16 C11 C10 -3.7(3) . . . . ? C7 C12 C11 C16 136.77(16) . . . . ? C7 C12 C11 C10 -42.67(18) . . . . ? C20 C10 C11 C16 116.49(18) . . . . ? C9 C10 C11 C16 -117.80(18) . . . . ? C20 C10 C11 C12 -64.11(17) . . . . ? C9 C10 C11 C12 61.60(17) . . . . ? C22 C21 C20 C25 -0.9(2) . . . . ? C22 C21 C20 C10 178.99(15) . . . . ? C24 C25 C20 C21 0.8(2) . . . . ? C24 C25 C20 C10 -179.04(15) . . . . ? C11 C10 C20 C21 117.40(17) . . . . ? C9 C10 C20 C21 -6.1(2) . . . . ? C11 C10 C20 C25 -62.74(18) . . . . ? C9 C10 C20 C25 173.76(14) . . . . ? C17 O3 C18 C19 -4.9(2) . . . . ? C17 N2 C19 C18 -14.6(2) . . . . ? C16 N2 C19 C18 -161.61(15) . . . . ? O3 C18 C19 N2 11.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.347 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.047 data_7a' _database_code_depnum_ccdc_archive 'CCDC 923924' #TrackingRef '7a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H44 N4 O8' _chemical_formula_sum 'C52 H44 N4 O8' _chemical_formula_weight 852.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall 'C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.7207(19) _cell_length_b 5.8026(2) _cell_length_c 28.3766(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.018(7) _cell_angle_gamma 90.00 _cell_volume 4480.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123.0(3) _cell_measurement_reflns_used 4931 _cell_measurement_theta_min 3.2242 _cell_measurement_theta_max 74.5999 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2028 _exptl_crystal_size_mid 0.0460 _exptl_crystal_size_min 0.0157 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.699 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.79819 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123.0(3) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.2640 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17465 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 88.49 _reflns_number_total 4272 _reflns_number_gt 3449 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SIR-2004 (Altomare, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2006)' _computing_publication_material 'SHELXL-97(Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.1239P)^2^+3.4169P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4272 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.1972 _refine_ls_wR_factor_gt 0.1809 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 C1 C 0.63097(8) 0.5090(4) 0.17568(8) 0.0315(5) Uani 1 1 d . . . C2 C 0.60517(8) 0.6467(4) 0.19987(8) 0.0324(5) Uani 1 1 d . . . C3 C 0.55268(8) 0.5490(4) 0.19122(8) 0.0315(5) Uani 1 1 d . . . H3 H 0.5476 0.4713 0.2206 0.038 Uiso 1 1 calc R . . C4 C 0.54676(8) 0.3710(4) 0.15045(8) 0.0303(5) Uani 1 1 d . . . C5 C 0.50076(8) 0.2961(4) 0.12176(8) 0.0310(5) Uani 1 1 d . . . H5 H 0.5016 0.1976 0.0961 0.037 Uiso 1 1 calc R . . C6 C 0.45224(8) 0.3685(4) 0.13119(8) 0.0297(5) Uani 1 1 d . . . H6 H 0.4423 0.2500 0.1520 0.036 Uiso 1 1 calc R . . C7 C 0.45789(8) 0.5930(4) 0.16050(7) 0.0295(5) Uani 1 1 d . . . C8 C 0.50808(8) 0.7187(4) 0.17401(8) 0.0332(5) Uani 1 1 d . . . H8A H 0.5064 0.8285 0.1994 0.040 Uiso 1 1 calc R . . H8B H 0.5141 0.8044 0.1463 0.040 Uiso 1 1 calc R . . C9 C 0.68160(9) 0.5561(4) 0.18052(8) 0.0376(5) Uani 1 1 d . . . H9 H 0.7008 0.4591 0.1656 0.045 Uiso 1 1 calc R . . C10 C 0.70463(9) 0.7507(5) 0.20791(9) 0.0404(6) Uani 1 1 d . . . H10 H 0.7380 0.7777 0.2099 0.048 Uiso 1 1 calc R . . C11 C 0.67829(9) 0.8916(4) 0.23024(9) 0.0402(6) Uani 1 1 d . . . H11 H 0.6924 1.0191 0.2474 0.048 Uiso 1 1 calc R . . C12 C 0.62834(9) 0.8383(4) 0.22661(8) 0.0367(5) Uani 1 1 d . . . H12 H 0.6094 0.9325 0.2424 0.044 Uiso 1 1 calc R . . C13 C 0.42000(8) 0.6857(4) 0.17341(8) 0.0304(5) Uani 1 1 d . . . H13 H 0.4247 0.8240 0.1902 0.036 Uiso 1 1 calc R . . C14 C 0.32398(9) 0.7233(4) 0.13905(9) 0.0396(6) Uani 1 1 d . . . C15 C 0.28380(10) 0.5755(4) 0.14993(12) 0.0481(7) Uani 1 1 d . . . C16 C 0.36000(9) 0.3800(4) 0.17797(8) 0.0328(5) Uani 1 1 d . . . C17 C 0.61069(9) 0.1812(4) 0.11676(8) 0.0339(5) Uani 1 1 d . . . C18 C 0.58472(10) -0.1273(4) 0.06015(9) 0.0442(6) Uani 1 1 d . . . H18A H 0.6102 -0.2278 0.0772 0.053 Uiso 1 1 calc R . . H18B H 0.5977 -0.0502 0.0349 0.053 Uiso 1 1 calc R . . C19 C 0.53850(10) -0.2761(4) 0.03715(9) 0.0446(6) Uani 1 1 d . . . H19A H 0.5264 -0.3569 0.0620 0.067 Uiso 1 1 calc R . . H19B H 0.5478 -0.3852 0.0151 0.067 Uiso 1 1 calc R . . H19C H 0.5133 -0.1767 0.0204 0.067 Uiso 1 1 calc R . . C20 C 0.40753(8) 0.3790(4) 0.08179(8) 0.0306(5) Uani 1 1 d . . . C21 C 0.37353(9) 0.1963(4) 0.06647(9) 0.0373(5) Uani 1 1 d . . . H21 H 0.3759 0.0641 0.0853 0.045 Uiso 1 1 calc R . . C22 C 0.33307(10) 0.2033(5) 0.02078(9) 0.0428(6) Uani 1 1 d . . . H22 H 0.3125 0.0763 0.0138 0.051 Uiso 1 1 calc R . . C23 C 0.32577(9) 0.3919(5) -0.01078(9) 0.0418(6) Uani 1 1 d . . . C24 C 0.35996(10) 0.5745(4) 0.00466(9) 0.0413(6) Uani 1 1 d . . . H24 H 0.3576 0.7064 -0.0142 0.050 Uiso 1 1 calc R . . C25 C 0.40008(9) 0.5684(4) 0.04999(8) 0.0365(5) Uani 1 1 d . . . H25 H 0.4206 0.6959 0.0569 0.044 Uiso 1 1 calc R . . C26 C 0.28286(11) 0.3967(6) -0.06081(10) 0.0574(8) Uani 1 1 d . . . H26A H 0.2949 0.3183 -0.0860 0.086 Uiso 1 1 calc R . . H26B H 0.2753 0.5536 -0.0701 0.086 Uiso 1 1 calc R . . H26C H 0.2537 0.3210 -0.0551 0.086 Uiso 1 1 calc R . . N1 N 0.59686(7) 0.3343(3) 0.14726(7) 0.0329(5) Uani 1 1 d . . . N2 N 0.37059(7) 0.5906(3) 0.16365(7) 0.0328(5) Uani 1 1 d . . . O1 O 0.65280(7) 0.1774(3) 0.11281(7) 0.0454(5) Uani 1 1 d . . . O2 O 0.57223(6) 0.0397(3) 0.09246(6) 0.0380(4) Uani 1 1 d . . . O3 O 0.38995(6) 0.2285(3) 0.19874(6) 0.0404(4) Uani 1 1 d . . . O4 O 0.30857(6) 0.3539(3) 0.16563(7) 0.0415(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0369(12) 0.0333(11) 0.0270(10) 0.0034(9) 0.0130(9) 0.0013(9) C2 0.0370(12) 0.0358(11) 0.0275(11) 0.0029(9) 0.0138(9) 0.0016(9) C3 0.0390(13) 0.0317(11) 0.0279(11) 0.0001(9) 0.0167(9) 0.0009(9) C4 0.0382(12) 0.0274(10) 0.0294(11) 0.0029(8) 0.0172(9) 0.0040(9) C5 0.0424(13) 0.0267(10) 0.0287(11) 0.0014(8) 0.0191(9) 0.0016(9) C6 0.0389(12) 0.0258(10) 0.0289(11) 0.0020(8) 0.0174(9) 0.0010(9) C7 0.0399(12) 0.0268(10) 0.0255(10) 0.0022(8) 0.0155(9) 0.0005(9) C8 0.0419(13) 0.0292(11) 0.0335(11) -0.0024(9) 0.0194(10) -0.0006(9) C9 0.0366(12) 0.0433(13) 0.0370(12) 0.0056(10) 0.0173(10) 0.0067(10) C10 0.0361(13) 0.0452(14) 0.0432(14) 0.0081(11) 0.0160(11) -0.0028(10) C11 0.0432(14) 0.0410(13) 0.0379(13) -0.0011(10) 0.0119(11) -0.0076(11) C12 0.0417(13) 0.0373(12) 0.0345(12) -0.0015(10) 0.0157(10) -0.0017(10) C13 0.0386(12) 0.0257(10) 0.0309(11) -0.0002(8) 0.0168(9) -0.0010(9) C14 0.0357(13) 0.0370(12) 0.0492(14) 0.0067(10) 0.0163(11) 0.0067(10) C15 0.0419(15) 0.0354(13) 0.0728(19) 0.0025(12) 0.0257(13) 0.0006(11) C16 0.0421(13) 0.0288(11) 0.0333(11) -0.0015(9) 0.0221(10) -0.0017(9) C17 0.0386(12) 0.0357(11) 0.0314(11) 0.0026(9) 0.0166(10) 0.0061(10) C18 0.0570(16) 0.0401(13) 0.0432(14) -0.0084(11) 0.0291(12) 0.0052(12) C19 0.0651(17) 0.0361(12) 0.0399(13) -0.0042(10) 0.0280(12) 0.0001(12) C20 0.0367(12) 0.0303(11) 0.0297(11) -0.0027(8) 0.0184(9) 0.0017(9) C21 0.0469(14) 0.0316(11) 0.0380(13) -0.0009(9) 0.0197(11) -0.0036(10) C22 0.0477(15) 0.0458(14) 0.0395(13) -0.0067(11) 0.0195(11) -0.0088(11) C23 0.0413(14) 0.0551(15) 0.0329(12) -0.0033(11) 0.0167(11) 0.0037(11) C24 0.0500(15) 0.0418(13) 0.0363(13) 0.0070(10) 0.0191(11) 0.0048(11) C25 0.0439(14) 0.0346(12) 0.0347(12) 0.0019(9) 0.0170(10) -0.0017(10) C26 0.0487(16) 0.086(2) 0.0386(15) 0.0010(14) 0.0108(13) -0.0016(16) N1 0.0369(11) 0.0337(10) 0.0322(10) -0.0007(8) 0.0170(8) 0.0025(8) N2 0.0368(11) 0.0303(9) 0.0359(10) 0.0006(7) 0.0186(8) 0.0016(8) O1 0.0444(10) 0.0510(11) 0.0480(10) -0.0050(8) 0.0270(8) 0.0043(8) O2 0.0454(10) 0.0366(9) 0.0386(9) -0.0064(7) 0.0244(7) 0.0033(7) O3 0.0518(11) 0.0326(8) 0.0442(9) 0.0060(7) 0.0277(8) 0.0022(7) O4 0.0427(10) 0.0354(9) 0.0530(11) -0.0006(7) 0.0258(8) -0.0028(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.345(3) . ? C1 C9 1.411(3) . ? C1 N1 1.510(3) . ? C2 C12 1.428(3) . ? C2 C3 1.537(3) . ? C3 C4 1.536(3) . ? C3 C8 1.583(3) . ? C3 H3 0.9800 . ? C4 N1 1.425(3) . ? C4 C5 1.442(3) . ? C5 C6 1.482(3) . ? C5 H5 0.9300 . ? C6 C7 1.537(3) . ? C6 C20 1.685(3) . ? C6 H6 0.9800 . ? C7 C13 1.294(3) . ? C7 C8 1.553(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.448(4) . ? C9 H9 0.9300 . ? C10 C11 1.334(4) . ? C10 H10 0.9300 . ? C11 C12 1.403(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N2 1.453(3) . ? C13 H13 0.9300 . ? C14 C15 1.484(3) . ? C14 N2 1.551(3) . ? C15 O4 1.485(3) . ? C16 O3 1.274(3) . ? C16 N2 1.338(3) . ? C16 O4 1.410(3) . ? C17 O1 1.194(3) . ? C17 N1 1.347(3) . ? C17 O2 1.416(3) . ? C18 O2 1.422(3) . ? C18 C19 1.579(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.412(3) . ? C20 C21 1.430(3) . ? C21 C22 1.544(4) . ? C21 H21 0.9300 . ? C22 C23 1.404(4) . ? C22 H22 0.9300 . ? C23 C24 1.433(4) . ? C23 C26 1.669(4) . ? C24 C25 1.532(4) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 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 C1 C9 116.9(2) . . ? C2 C1 N1 109.35(19) . . ? C9 C1 N1 133.8(2) . . ? C1 C2 C12 120.3(2) . . ? C1 C2 C3 106.2(2) . . ? C12 C2 C3 133.5(2) . . ? C4 C3 C2 109.26(17) . . ? C4 C3 C8 102.78(18) . . ? C2 C3 C8 118.68(18) . . ? C4 C3 H3 108.6 . . ? C2 C3 H3 108.6 . . ? C8 C3 H3 108.6 . . ? N1 C4 C5 133.35(19) . . ? N1 C4 C3 100.55(18) . . ? C5 C4 C3 125.67(19) . . ? C4 C5 C6 123.23(19) . . ? C4 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C5 C6 C7 109.62(19) . . ? C5 C6 C20 114.12(16) . . ? C7 C6 C20 113.70(17) . . ? C5 C6 H6 106.3 . . ? C7 C6 H6 106.3 . . ? C20 C6 H6 106.3 . . ? C13 C7 C6 120.1(2) . . ? C13 C7 C8 118.2(2) . . ? C6 C7 C8 121.69(18) . . ? C7 C8 C3 113.23(17) . . ? C7 C8 H8A 108.9 . . ? C3 C8 H8A 108.9 . . ? C7 C8 H8B 108.9 . . ? C3 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C1 C9 C10 122.1(2) . . ? C1 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 120.5(2) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 116.9(2) . . ? C10 C11 H11 121.6 . . ? C12 C11 H11 121.6 . . ? C11 C12 C2 123.2(2) . . ? C11 C12 H12 118.4 . . ? C2 C12 H12 118.4 . . ? C7 C13 N2 125.1(2) . . ? C7 C13 H13 117.5 . . ? N2 C13 H13 117.5 . . ? C15 C14 N2 102.30(19) . . ? C14 C15 O4 103.92(19) . . ? O3 C16 N2 127.5(2) . . ? O3 C16 O4 125.44(19) . . ? N2 C16 O4 107.0(2) . . ? O1 C17 N1 118.4(2) . . ? O1 C17 O2 127.0(2) . . ? N1 C17 O2 114.53(19) . . ? O2 C18 C19 111.1(2) . . ? O2 C18 H18A 109.4 . . ? C19 C18 H18A 109.4 . . ? O2 C18 H18B 109.4 . . ? C19 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 112.0(2) . . ? C25 C20 C6 123.7(2) . . ? C21 C20 C6 124.29(19) . . ? C20 C21 C22 124.5(2) . . ? C20 C21 H21 117.7 . . ? C22 C21 H21 117.7 . . ? C23 C22 C21 123.3(2) . . ? C23 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? C22 C23 C24 112.0(2) . . ? C22 C23 C26 123.2(2) . . ? C24 C23 C26 124.7(2) . . ? C23 C24 C25 124.8(2) . . ? C23 C24 H24 117.6 . . ? C25 C24 H24 117.6 . . ? C20 C25 C24 123.3(2) . . ? C20 C25 H25 118.4 . . ? C24 C25 H25 118.4 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C17 N1 C4 122.7(2) . . ? C17 N1 C1 124.06(19) . . ? C4 N1 C1 112.61(17) . . ? C16 N2 C13 122.9(2) . . ? C16 N2 C14 112.21(19) . . ? C13 N2 C14 124.80(18) . . ? C17 O2 C18 117.09(18) . . ? C16 O4 C15 111.66(17) . . ? 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 C1 C2 C12 3.6(3) . . . . ? N1 C1 C2 C12 -175.06(19) . . . . ? C9 C1 C2 C3 -176.28(19) . . . . ? N1 C1 C2 C3 5.1(2) . . . . ? C1 C2 C3 C4 -12.4(2) . . . . ? C12 C2 C3 C4 167.7(2) . . . . ? C1 C2 C3 C8 -129.7(2) . . . . ? C12 C2 C3 C8 50.5(3) . . . . ? C2 C3 C4 N1 14.2(2) . . . . ? C8 C3 C4 N1 141.09(16) . . . . ? C2 C3 C4 C5 -159.1(2) . . . . ? C8 C3 C4 C5 -32.2(3) . . . . ? N1 C4 C5 C6 -176.7(2) . . . . ? C3 C4 C5 C6 -5.7(3) . . . . ? C4 C5 C6 C7 21.7(3) . . . . ? C4 C5 C6 C20 150.56(19) . . . . ? C5 C6 C7 C13 -179.02(19) . . . . ? C20 C6 C7 C13 51.9(3) . . . . ? C5 C6 C7 C8 3.0(3) . . . . ? C20 C6 C7 C8 -126.1(2) . . . . ? C13 C7 C8 C3 139.2(2) . . . . ? C6 C7 C8 C3 -42.7(3) . . . . ? C4 C3 C8 C7 52.1(2) . . . . ? C2 C3 C8 C7 172.72(17) . . . . ? C2 C1 C9 C10 -3.4(3) . . . . ? N1 C1 C9 C10 174.8(2) . . . . ? C1 C9 C10 C11 0.9(4) . . . . ? C9 C10 C11 C12 1.4(4) . . . . ? C10 C11 C12 C2 -1.2(4) . . . . ? C1 C2 C12 C11 -1.4(4) . . . . ? C3 C2 C12 C11 178.4(2) . . . . ? C6 C7 C13 N2 2.0(3) . . . . ? C8 C7 C13 N2 -179.97(19) . . . . ? N2 C14 C15 O4 -15.5(3) . . . . ? C5 C6 C20 C25 -82.9(2) . . . . ? C7 C6 C20 C25 43.9(3) . . . . ? C5 C6 C20 C21 95.6(2) . . . . ? C7 C6 C20 C21 -137.7(2) . . . . ? C25 C20 C21 C22 -0.3(3) . . . . ? C6 C20 C21 C22 -178.90(19) . . . . ? C20 C21 C22 C23 0.4(4) . . . . ? C21 C22 C23 C24 -0.3(3) . . . . ? C21 C22 C23 C26 178.5(2) . . . . ? C22 C23 C24 C25 0.1(3) . . . . ? C26 C23 C24 C25 -178.6(2) . . . . ? C21 C20 C25 C24 0.2(3) . . . . ? C6 C20 C25 C24 178.79(18) . . . . ? C23 C24 C25 C20 -0.1(4) . . . . ? O1 C17 N1 C4 172.5(2) . . . . ? O2 C17 N1 C4 -7.4(3) . . . . ? O1 C17 N1 C1 2.4(3) . . . . ? O2 C17 N1 C1 -177.58(18) . . . . ? C5 C4 N1 C17 -10.0(4) . . . . ? C3 C4 N1 C17 177.5(2) . . . . ? C5 C4 N1 C1 161.2(2) . . . . ? C3 C4 N1 C1 -11.4(2) . . . . ? C2 C1 N1 C17 175.5(2) . . . . ? C9 C1 N1 C17 -2.8(4) . . . . ? C2 C1 N1 C4 4.4(2) . . . . ? C9 C1 N1 C4 -173.9(2) . . . . ? O3 C16 N2 C13 -4.7(3) . . . . ? O4 C16 N2 C13 175.48(17) . . . . ? O3 C16 N2 C14 179.2(2) . . . . ? O4 C16 N2 C14 -0.6(2) . . . . ? C7 C13 N2 C16 57.6(3) . . . . ? C7 C13 N2 C14 -126.8(2) . . . . ? C15 C14 N2 C16 10.8(3) . . . . ? C15 C14 N2 C13 -165.2(2) . . . . ? O1 C17 O2 C18 0.7(3) . . . . ? N1 C17 O2 C18 -179.3(2) . . . . ? C19 C18 O2 C17 178.25(19) . . . . ? O3 C16 O4 C15 169.8(2) . . . . ? N2 C16 O4 C15 -10.4(2) . . . . ? C14 C15 O4 C16 17.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.833 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.713 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.068 data_ruben _database_code_depnum_ccdc_archive 'CCDC 924119' #TrackingRef '17653_web_deposit_cif_file_0_RubenVicente_1360584081.ruben.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H45 Cl2 N3 O7' _chemical_formula_weight 714.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _cell_length_a 12.9978(8) _cell_length_b 22.7937(14) _cell_length_c 12.2394(8) _cell_angle_alpha 90.0 _cell_angle_beta 91.808(5) _cell_angle_gamma 90.0 _cell_volume 3624.4(4) _cell_formula_units_Z 4.00000 _cell_measurement_temperature 123.00(10) _cell_measurement_reflns_used 1270 _cell_measurement_theta_min 3.3992 _cell_measurement_theta_max 40.6523 _exptl_crystal_size_max 0.1248 _exptl_crystal_size_mid 0.0625 _exptl_crystal_size_min 0.0317 _diffrn_ambient_temperature 123.00(10) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_detector_area_resol_mean 8.2640 _diffrn_reflns_number 4608 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.3992 _diffrn_reflns_theta_max 40.6523 _diffrn_orient_matrix_UB_11 0.0843732000 _diffrn_orient_matrix_UB_12 -0.0328469000 _diffrn_orient_matrix_UB_13 0.0667268000 _diffrn_orient_matrix_UB_21 -0.0825642000 _diffrn_orient_matrix_UB_22 -0.0264388000 _diffrn_orient_matrix_UB_23 0.0729727000 _diffrn_orient_matrix_UB_31 -0.0110494000 _diffrn_orient_matrix_UB_32 -0.0528289000 _diffrn_orient_matrix_UB_33 -0.0779941000 _diffrn_measurement_method '\w scans' _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_cell_setting monoclinic _reflns_odcompleteness_completeness 99.26 _reflns_odcompleteness_theta 39.93 _reflns_odcompleteness_iscentric 1 _chemical_oxdiff_formula 'C32 H33 N3 O6' _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^)+(0.2000P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2219 _refine_ls_number_parameters 431 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1387 _refine_ls_R_factor_gt 0.1129 _refine_ls_wR_factor_ref 0.3450 _refine_ls_wR_factor_gt 0.3185 _refine_ls_goodness_of_fit_ref 1.429 _refine_ls_restrained_S_all 1.429 _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 C1 C 0.6301(9) 0.5957(6) 0.4359(10) 0.054(4) Uani 1 1 d . . . H1 H 0.6151 0.5983 0.3571 0.065 Uiso 1 1 calc R . . C2 C 0.6803(10) 0.6533(5) 0.4721(11) 0.052(3) Uani 1 1 d . . . H2 H 0.6254 0.6828 0.4733 0.063 Uiso 1 1 calc R . . C3 C 0.7213(9) 0.6470(5) 0.5871(13) 0.059(4) Uani 1 1 d . . . C4 C 0.8049(9) 0.5998(7) 0.6017(10) 0.066(4) Uani 1 1 d . . . H4A H 0.8710 0.6162 0.5832 0.079 Uiso 1 1 calc R . . H4B H 0.8092 0.5875 0.6775 0.079 Uiso 1 1 calc R . . C5 C 0.7818(14) 0.5471(7) 0.5299(13) 0.050(3) Uani 1 1 d . . . C6 C 0.8347(13) 0.4936(8) 0.5258(13) 0.058(4) Uani 1 1 d . . . C7 C 0.9187(13) 0.4715(8) 0.5858(11) 0.064(4) Uani 1 1 d . . . H7 H 0.9501 0.4933 0.6418 0.076 Uiso 1 1 calc R . . C8 C 0.9547(9) 0.4157(8) 0.5594(12) 0.068(4) Uani 1 1 d . . . H8 H 1.0113 0.4002 0.5979 0.081 Uiso 1 1 calc R . . C9 C 0.9083(10) 0.3836(6) 0.4787(12) 0.068(4) Uani 1 1 d U . . H9 H 0.9324 0.3460 0.4647 0.082 Uiso 1 1 calc R . . C10 C 0.8267(9) 0.4052(6) 0.4169(11) 0.060(3) Uani 1 1 d U . . H10 H 0.7983 0.3838 0.3587 0.072 Uiso 1 1 calc R . . C11 C 0.7880(13) 0.4597(7) 0.4439(14) 0.060(4) Uani 1 1 d U . . N12 N 0.7065(10) 0.4933(6) 0.3949(12) 0.057(3) Uani 1 1 d . . . C13 C 0.7055(13) 0.5468(7) 0.4548(15) 0.052(3) Uani 1 1 d . . . C14 C 0.6386(15) 0.4792(9) 0.3081(14) 0.065(4) Uani 1 1 d . . . O15 O 0.5677(9) 0.5092(5) 0.2801(8) 0.085(4) Uani 1 1 d . . . O16 O 0.6670(6) 0.4281(5) 0.2640(9) 0.073(3) Uani 1 1 d . . . C17 C 0.5998(11) 0.4098(7) 0.1743(15) 0.095(5) Uani 1 1 d . . . H17A H 0.5910 0.4416 0.1221 0.114 Uiso 1 1 calc R . . H17B H 0.5327 0.3995 0.2011 0.114 Uiso 1 1 calc R . . C18 C 0.6471(11) 0.3578(7) 0.1202(13) 0.113(6) Uani 1 1 d . . . H18A H 0.6047 0.3462 0.0583 0.170 Uiso 1 1 calc R . . H18B H 0.6524 0.3259 0.1713 0.170 Uiso 1 1 calc R . . H18C H 0.7144 0.3680 0.0964 0.170 Uiso 1 1 calc R . . C19 C 0.5267(10) 0.5865(5) 0.4931(9) 0.054(4) Uani 1 1 d . . . H19A H 0.5050 0.5463 0.4812 0.065 Uiso 1 1 calc R . . H19B H 0.5388 0.5917 0.5711 0.065 Uiso 1 1 calc R . . C20 C 0.4429(11) 0.6248(8) 0.4583(12) 0.059(4) Uani 1 1 d . . . H20 H 0.4183 0.6213 0.3864 0.071 Uiso 1 1 calc R . . C21 C 0.3990(14) 0.6638(8) 0.5194(11) 0.056(4) Uani 1 1 d . . . H21 H 0.4225 0.6676 0.5916 0.067 Uiso 1 1 calc R . . N22 N 0.3205(12) 0.6992(7) 0.4833(11) 0.062(4) Uani 1 1 d . . . C23 C 0.2666(14) 0.7330(8) 0.5504(18) 0.063(5) Uani 1 1 d . . . O24 O 0.2852(7) 0.7436(4) 0.6463(10) 0.076(3) Uani 1 1 d . . . O25 O 0.1855(8) 0.7577(4) 0.4984(10) 0.078(3) Uani 1 1 d . . . C26 C 0.1802(10) 0.7379(6) 0.3874(14) 0.084(5) Uani 1 1 d . . . H26A H 0.1889 0.7705 0.3376 0.101 Uiso 1 1 calc R . . H26B H 0.1142 0.7194 0.3708 0.101 Uiso 1 1 calc R . . C27 C 0.2665(12) 0.6942(6) 0.3770(12) 0.079(4) Uani 1 1 d . . . H27A H 0.2402 0.6548 0.3651 0.095 Uiso 1 1 calc R . . H27B H 0.3110 0.7046 0.3179 0.095 Uiso 1 1 calc R . . C28 C 0.7618(10) 0.6769(7) 0.3978(12) 0.052(3) Uani 1 1 d . . . C29 C 0.8116(12) 0.7278(8) 0.4226(11) 0.064(4) Uani 1 1 d . . . H29 H 0.7976 0.7464 0.4882 0.077 Uiso 1 1 calc R . . C30 C 0.8800(12) 0.7526(6) 0.3569(17) 0.075(4) Uani 1 1 d . . . H30 H 0.9112 0.7878 0.3777 0.090 Uiso 1 1 calc R . . C31 C 0.9050(9) 0.7273(8) 0.2601(15) 0.072(4) Uani 1 1 d . . . C32 C 0.9798(10) 0.7570(6) 0.1820(11) 0.087(4) Uiso 1 1 d . . . H32A H 0.9875 0.7329 0.1185 0.131 Uiso 1 1 calc R . . H32B H 1.0456 0.7621 0.2186 0.131 Uiso 1 1 calc R . . H32C H 0.9529 0.7946 0.1602 0.131 Uiso 1 1 calc R . . C33 C 0.8558(11) 0.6758(7) 0.2320(12) 0.076(4) Uani 1 1 d U . . H33 H 0.8693 0.6577 0.1659 0.091 Uiso 1 1 calc R . . C34 C 0.7863(9) 0.6510(6) 0.3017(13) 0.069(4) Uani 1 1 d U . . H34 H 0.7554 0.6155 0.2825 0.083 Uiso 1 1 calc R . . C35 C 0.6863(11) 0.6750(6) 0.6779(11) 0.060(4) Uiso 1 1 d . . . H35 H 0.7151 0.6626 0.7445 0.072 Uiso 1 1 calc R . . N36 N 0.6153(8) 0.7184(5) 0.6833(12) 0.068(4) Uani 1 1 d . . . C37 C 0.5755(12) 0.7271(7) 0.784(2) 0.078(6) Uani 1 1 d . . . O38 O 0.5814(8) 0.6969(6) 0.8647(10) 0.097(4) Uani 1 1 d . . . O39 O 0.5241(7) 0.7785(6) 0.7825(9) 0.088(3) Uani 1 1 d . . . C40 C 0.5257(10) 0.8055(6) 0.6746(15) 0.083(4) Uani 1 1 d . . . H40A H 0.5456 0.8465 0.6800 0.099 Uiso 1 1 calc R . . H40B H 0.4585 0.8030 0.6379 0.099 Uiso 1 1 calc R . . C41 C 0.6052(11) 0.7704(6) 0.6133(12) 0.074(4) Uani 1 1 d . . . H41C H 0.5804 0.7603 0.5401 0.089 Uiso 1 1 calc R . . H41D H 0.6699 0.7914 0.6092 0.089 Uiso 1 1 calc R . . C80 C 0.1570(17) 0.8918(9) 0.6436(14) 0.139(7) Uani 1 1 d . . . H80A H 0.1652 0.8570 0.6874 0.208 Uiso 1 1 calc R . . H80B H 0.1570 0.8814 0.5676 0.208 Uiso 1 1 calc R . . H80C H 0.0930 0.9104 0.6596 0.208 Uiso 1 1 calc R . . C81 C 0.7519(18) 0.4350(13) -0.1702(17) 0.172(10) Uani 1 1 d . . . H81A H 0.7601 0.4524 -0.2416 0.207 Uiso 1 1 calc R . . H81B H 0.6871 0.4138 -0.1711 0.207 Uiso 1 1 calc R . . O82 O 0.7513(12) 0.4790(6) -0.0900(13) 0.148(5) Uani 1 1 d . . . C83 C 0.3205(19) 0.4783(11) 0.110(2) 0.187(10) Uani 1 1 d U . . H83A H 0.3060 0.4595 0.1788 0.225 Uiso 1 1 calc R . . H83B H 0.3877 0.4966 0.1177 0.225 Uiso 1 1 calc R . . C84 C 0.325(2) 0.4304(10) 0.020(2) 0.215(10) Uani 1 1 d U . . H84A H 0.3738 0.4008 0.0423 0.323 Uiso 1 1 calc R . . H84B H 0.3455 0.4479 -0.0471 0.323 Uiso 1 1 calc R . . H84C H 0.2581 0.4129 0.0097 0.323 Uiso 1 1 calc R . . C901 C 1.104(2) 0.5452(12) 0.860(2) 0.078(9) Uiso 0.56(3) 1 d P A 1 H90A H 1.1128 0.5397 0.9380 0.094 Uiso 0.56(3) 1 calc PR A 1 H90B H 1.1679 0.5632 0.8374 0.094 Uiso 0.56(3) 1 calc PR A 1 Cl21 Cl 1.0284(13) 0.5953(7) 0.8509(11) 0.178(7) Uiso 0.56(3) 1 d P A 1 C902 C 1.051(3) 0.5205(13) 0.902(2) 0.063(11) Uiso 0.44(3) 1 d P A 2 H90C H 1.0136 0.4934 0.9468 0.076 Uiso 0.44(3) 1 calc PR A 2 H90D H 1.1050 0.5370 0.9493 0.076 Uiso 0.44(3) 1 calc PR A 2 Cl22 Cl 0.9795(17) 0.5692(10) 0.8783(14) 0.180(9) Uiso 0.44(3) 1 d P A 2 Cl1 Cl 1.1130(4) 0.4781(3) 0.8121(5) 0.165(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.032(9) 0.077(11) 0.054(8) 0.002(8) 0.005(7) -0.014(10) C2 0.041(9) 0.065(10) 0.051(10) -0.001(8) -0.011(9) 0.005(8) C3 0.030(8) 0.039(8) 0.106(14) -0.004(8) 0.000(8) 0.003(7) C4 0.061(10) 0.086(11) 0.050(8) -0.008(10) 0.009(7) -0.005(10) C5 0.025(10) 0.063(13) 0.062(11) -0.005(11) 0.011(9) 0.010(11) C6 0.022(10) 0.087(15) 0.067(12) 0.016(12) 0.023(10) 0.003(12) C7 0.046(11) 0.077(12) 0.070(10) -0.016(9) 0.013(10) -0.010(9) C8 0.041(9) 0.079(12) 0.084(12) 0.011(10) 0.016(9) 0.015(9) C9 0.054(8) 0.073(9) 0.078(9) -0.015(8) 0.011(7) -0.006(8) C10 0.039(7) 0.075(8) 0.067(8) -0.011(7) 0.017(6) -0.011(7) C11 0.042(9) 0.076(9) 0.063(9) -0.007(9) 0.020(7) -0.010(10) N12 0.043(10) 0.060(10) 0.070(10) 0.003(10) 0.017(9) 0.000(8) C13 0.035(11) 0.058(14) 0.063(11) 0.003(11) 0.009(10) 0.001(11) C14 0.055(14) 0.085(17) 0.054(12) -0.006(12) 0.002(13) -0.018(13) O15 0.061(7) 0.094(8) 0.099(8) -0.011(6) -0.014(6) 0.014(6) O16 0.061(7) 0.073(7) 0.084(8) -0.026(6) 0.007(6) 0.001(6) C17 0.062(10) 0.088(12) 0.134(14) -0.037(11) -0.016(11) -0.009(9) C18 0.087(11) 0.132(15) 0.121(13) -0.032(12) 0.001(10) -0.013(11) C19 0.048(9) 0.059(8) 0.057(9) -0.001(7) 0.019(8) -0.017(9) C20 0.017(9) 0.086(11) 0.075(10) 0.020(10) -0.001(8) 0.000(9) C21 0.020(9) 0.070(10) 0.080(11) -0.004(10) 0.020(9) 0.012(9) N22 0.036(9) 0.070(8) 0.083(12) -0.016(9) 0.024(10) 0.006(8) C23 0.029(11) 0.077(12) 0.084(16) 0.029(14) -0.010(14) 0.012(10) O24 0.063(7) 0.096(8) 0.067(7) -0.006(6) 0.006(6) 0.009(5) O25 0.061(7) 0.103(7) 0.070(8) -0.007(6) 0.022(6) 0.019(6) C26 0.054(10) 0.107(12) 0.093(15) -0.004(10) 0.020(9) 0.034(9) C27 0.075(11) 0.116(13) 0.047(10) 0.001(9) -0.009(9) -0.008(11) C28 0.040(9) 0.054(10) 0.061(12) 0.007(9) 0.008(9) -0.016(9) C29 0.044(9) 0.086(13) 0.064(10) 0.017(10) 0.025(10) -0.004(9) C30 0.056(11) 0.082(11) 0.087(13) 0.012(12) 0.007(10) -0.005(9) C31 0.028(8) 0.112(14) 0.076(12) 0.050(11) 0.023(9) -0.003(9) C33 0.054(8) 0.093(10) 0.080(10) -0.001(8) 0.007(7) -0.027(8) C34 0.043(8) 0.086(9) 0.078(10) 0.005(8) 0.011(7) -0.030(7) N36 0.048(7) 0.090(11) 0.068(9) -0.039(9) 0.020(7) 0.029(7) C37 0.041(10) 0.037(13) 0.15(3) -0.047(13) -0.012(15) 0.006(9) O38 0.085(8) 0.120(11) 0.088(9) -0.007(7) 0.023(7) -0.012(7) O39 0.067(7) 0.114(10) 0.083(9) -0.029(7) 0.013(6) 0.000(7) C40 0.052(10) 0.079(11) 0.116(15) -0.021(12) -0.008(9) 0.020(8) C41 0.076(10) 0.062(9) 0.085(11) 0.017(10) 0.004(9) 0.009(8) C80 0.143(17) 0.159(17) 0.112(15) 0.004(13) -0.018(13) 0.037(15) C81 0.15(2) 0.25(3) 0.114(17) -0.09(2) 0.018(16) -0.04(2) O82 0.163(13) 0.131(11) 0.147(12) 0.028(10) -0.053(10) -0.015(9) C83 0.159(17) 0.16(2) 0.23(3) 0.058(17) -0.081(19) -0.016(17) C84 0.232(18) 0.15(2) 0.26(3) 0.035(16) -0.11(2) 0.008(17) Cl1 0.152(5) 0.183(5) 0.160(5) -0.010(4) 0.000(4) 0.012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C13 1.499(17) . ? C1 C2 1.526(15) . ? C1 C19 1.548(14) . ? C2 C3 1.496(16) . ? C2 C28 1.516(16) . ? C3 C35 1.371(16) . ? C3 C4 1.536(15) . ? C4 C5 1.512(17) . ? C5 C13 1.331(15) . ? C5 C6 1.401(17) . ? C6 C11 1.389(17) . ? C6 C7 1.391(18) . ? C7 C8 1.397(16) . ? C8 C9 1.355(16) . ? C9 C10 1.374(16) . ? C10 C11 1.385(18) . ? C11 N12 1.424(18) . ? N12 C14 1.397(17) . ? N12 C13 1.422(16) . ? C14 O15 1.188(17) . ? C14 O16 1.342(17) . ? O16 C17 1.442(15) . ? C17 C18 1.499(18) . ? C19 C20 1.449(16) . ? C20 C21 1.304(17) . ? C21 N22 1.364(17) . ? N22 C23 1.341(18) . ? N22 C27 1.462(16) . ? C23 O24 1.215(17) . ? C23 O25 1.337(15) . ? O25 C26 1.432(15) . ? C26 C27 1.509(16) . ? C28 C29 1.358(15) . ? C28 C34 1.363(16) . ? C29 C30 1.343(18) . ? C30 C31 1.366(18) . ? C31 C33 1.374(18) . ? C31 C32 1.542(18) . ? C33 C34 1.384(17) . ? C35 N36 1.358(16) . ? N36 C37 1.37(2) . ? N36 C41 1.465(14) . ? C37 O38 1.20(2) . ? C37 O39 1.347(16) . ? O39 C40 1.458(15) . ? C40 C41 1.523(17) . ? C80 C81 1.57(3) 2_655 ? C81 O82 1.40(2) . ? C81 C80 1.57(3) 2_645 ? O82 C83 1.36(2) 3_665 ? C83 O82 1.36(2) 3_665 ? C83 C84 1.55(3) . ? C901 Cl21 1.51(2) . ? C901 Cl1 1.64(2) . ? C902 Cl22 1.47(3) . ? C902 Cl1 1.69(3) . ? 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 C13 C1 C2 108.9(11) . . ? C13 C1 C19 113.7(10) . . ? C2 C1 C19 110.8(10) . . ? C3 C2 C28 111.4(10) . . ? C3 C2 C1 109.0(10) . . ? C28 C2 C1 115.6(11) . . ? C35 C3 C2 126.9(11) . . ? C35 C3 C4 118.9(13) . . ? C2 C3 C4 114.0(11) . . ? C5 C4 C3 111.2(11) . . ? C13 C5 C6 109.0(13) . . ? C13 C5 C4 122.4(17) . . ? C6 C5 C4 128.5(18) . . ? C11 C6 C7 119.8(17) . . ? C11 C6 C5 107.8(14) . . ? C7 C6 C5 132.4(18) . . ? C6 C7 C8 118.1(13) . . ? C9 C8 C7 121.0(13) . . ? C8 C9 C10 121.8(13) . . ? C9 C10 C11 118.0(13) . . ? C10 C11 C6 121.2(18) . . ? C10 C11 N12 130.8(16) . . ? C6 C11 N12 107.9(14) . . ? C14 N12 C13 125.0(15) . . ? C14 N12 C11 129.8(16) . . ? C13 N12 C11 105.2(13) . . ? C5 C13 N12 110.0(13) . . ? C5 C13 C1 124.9(17) . . ? N12 C13 C1 125.1(17) . . ? O15 C14 O16 127.2(17) . . ? O15 C14 N12 123.5(17) . . ? O16 C14 N12 109.3(18) . . ? C14 O16 C17 112.9(13) . . ? O16 C17 C18 108.5(13) . . ? C20 C19 C1 116.2(10) . . ? C21 C20 C19 125.5(14) . . ? C20 C21 N22 123.6(13) . . ? C23 N22 C21 122.8(14) . . ? C23 N22 C27 110.2(14) . . ? C21 N22 C27 125.1(13) . . ? O24 C23 O25 120(2) . . ? O24 C23 N22 127.9(16) . . ? O25 C23 N22 111.6(18) . . ? C23 O25 C26 109.5(13) . . ? O25 C26 C27 105.9(11) . . ? N22 C27 C26 102.2(12) . . ? C29 C28 C34 116.2(12) . . ? C29 C28 C2 120.4(14) . . ? C34 C28 C2 123.4(14) . . ? C30 C29 C28 123.0(13) . . ? C29 C30 C31 121.5(13) . . ? C30 C31 C33 117.1(12) . . ? C30 C31 C32 121.5(18) . . ? C33 C31 C32 121.2(18) . . ? C31 C33 C34 120.2(13) . . ? C28 C34 C33 121.9(12) . . ? N36 C35 C3 128.5(12) . . ? C35 N36 C37 115.2(13) . . ? C35 N36 C41 127.6(12) . . ? C37 N36 C41 112.4(13) . . ? O38 C37 O39 122(2) . . ? O38 C37 N36 129.7(16) . . ? O39 C37 N36 108.1(18) . . ? C37 O39 C40 111.3(14) . . ? O39 C40 C41 104.6(10) . . ? N36 C41 C40 100.8(11) . . ? O82 C81 C80 109.0(19) . 2_645 ? C83 O82 C81 114(2) 3_665 . ? O82 C83 C84 115(2) 3_665 . ? Cl21 C901 Cl1 137.0(17) . . ? Cl22 C902 Cl1 128(2) . . ? C901 Cl1 C902 36.4(10) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 40.69 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.471 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.093