# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_shelxl _audit_creation_date 2013-09-11 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C35 H41 N O4' _chemical_formula_sum 'C1 H1 N1 O1 ' _chemical_formula_weight 539.69 _chemical_absolute_configuration unk _chemical_melting_point ? 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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 'x+1/2, -y+1/2, -z' 3 '-x, y+1/2, -z+1/2' 4 '-x+1/2, -y, z+1/2' _cell_length_a 7.5322(15) _cell_length_b 16.363(3) _cell_length_c 24.127(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2973.6(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5303 _cell_measurement_temperature 293.1500 _cell_measurement_theta_max 25.3491 _cell_measurement_theta_min 3.0088 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7357 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details ? _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1160 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1920 _diffrn_reflns_av_unetI/netI 0.1536 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 29125 _diffrn_reflns_theta_full 25.35 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_min 3.01 _diffrn_ambient_temperature 293.1500 _diffrn_detector_area_resol_mean 14.6306 _diffrn_measured_fraction_theta_full 100.0000 _diffrn_measured_fraction_theta_max 25.3491 _diffrn_measurement_details ; scan: Number of images: 360 Slice: -80.0000 - 100.0000 Image width: 0.5000 Exp time: 6.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 35.2974 2theta: 9.9856 scan: Number of images: 360 Slice: -80.0000 - 100.0000 Image width: 0.5000 Exp time: 6.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 35.2974 2theta: 9.9856 ; _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_measurement_device_details ; AFC8: Eulerian 3-circle ; _diffrn_measurement_device_type ? _diffrn_measurement_method dtprofit.ref _diffrn_number_total 0 _diffrn_orient_matrix_type d*Trek _diffrn_orient_matrix_UB_11 0.0033 _diffrn_orient_matrix_UB_12 -0.0383 _diffrn_orient_matrix_UB_13 -0.1271 _diffrn_orient_matrix_UB_21 0.0453 _diffrn_orient_matrix_UB_22 0.0396 _diffrn_orient_matrix_UB_23 -0.0108 _diffrn_orient_matrix_UB_31 0.0278 _diffrn_orient_matrix_UB_32 -0.0292 _diffrn_orient_matrix_UB_33 0.0095 _diffrn_radiation_detector CCD _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_type Molybdenum _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Sealed Tube' _diffrn_source_current 40.0000 _diffrn_source_power 2.0000 _diffrn_source_voltage 50.0000 _diffrn_special_details ; ? ; _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2720 _reflns_number_total 5428 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; ???? ; _refine_diff_density_max 0.183 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.043 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(4) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 415 _refine_ls_number_reflns 5428 _refine_ls_number_restraints 1694 _refine_ls_R_factor_all 0.2486 _refine_ls_R_factor_gt 0.1379 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+1.4921P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2417 _refine_ls_wR_factor_ref 0.2804 _refine_special_details 47 _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O3 O 0.4411(6) 0.6801(3) 0.6516(2) 0.0675(13) Uani 1 1 d U . . O4 O 0.7763(8) 0.6930(3) 0.4953(2) 0.0918(18) Uani 1 1 d U . . N1 N 0.6283(8) 0.7033(4) 0.5773(3) 0.0697(15) Uani 1 1 d U B . C1 C 0.3717(10) 0.6268(4) 0.5592(3) 0.0609(16) Uani 1 1 d U . . H1 H 0.2634 0.6568 0.5495 0.073 Uiso 1 1 calc R . . C2 C 0.4953(9) 0.6217(4) 0.5092(3) 0.0577(16) Uani 1 1 d U . . H2 H 0.4349 0.6444 0.4767 0.069 Uiso 1 1 calc R . . C3 C 0.5396(9) 0.5291(4) 0.4983(3) 0.0563(16) Uani 1 1 d U . . C4 C 0.6742(10) 0.5204(4) 0.4507(3) 0.0618(17) Uani 1 1 d U . . H4A H 0.7905 0.5372 0.4636 0.074 Uiso 1 1 calc R . . H4B H 0.6402 0.5565 0.4206 0.074 Uiso 1 1 calc R . . C5 C 0.6847(9) 0.4329(4) 0.4290(3) 0.0605(17) Uani 1 1 d U . . H5A H 0.7692 0.4303 0.3987 0.073 Uiso 1 1 calc R . . H5B H 0.7263 0.3971 0.4583 0.073 Uiso 1 1 calc R . . C6 C 0.5038(9) 0.4040(4) 0.4089(3) 0.0586(16) Uani 1 1 d U A . H6 H 0.4597 0.4489 0.3858 0.070 Uiso 1 1 calc R . . C7 C 0.5058(10) 0.3292(4) 0.3701(3) 0.0671(18) Uani 1 1 d U . . C8 C 0.3154(10) 0.3129(5) 0.3506(3) 0.0747(19) Uani 1 1 d U A . H8A H 0.2765 0.3582 0.3276 0.090 Uiso 1 1 calc R . . H8B H 0.3141 0.2639 0.3280 0.090 Uiso 1 1 calc R . . C9 C 0.1850(10) 0.3023(5) 0.3985(3) 0.0730(19) Uani 1 1 d U . . H9A H 0.0668 0.2929 0.3839 0.088 Uiso 1 1 calc R A . H9B H 0.2186 0.2550 0.4203 0.088 Uiso 1 1 calc R . . C10 C 0.1834(11) 0.3787(5) 0.4358(3) 0.073(2) Uani 1 1 d U A . H10A H 0.1033 0.3695 0.4667 0.088 Uiso 1 1 calc R . . H10B H 0.1384 0.4248 0.4147 0.088 Uiso 1 1 calc R . . C11 C 0.3723(9) 0.4004(4) 0.4589(3) 0.0604(16) Uani 1 1 d U . . C12 C 0.3591(9) 0.4884(4) 0.4830(3) 0.0534(16) Uani 1 1 d U A . H12 H 0.3078 0.5221 0.4535 0.064 Uiso 1 1 calc R . . C13 C 0.2300(9) 0.4958(5) 0.5332(3) 0.0655(17) Uani 1 1 d U . . H13A H 0.1248 0.5260 0.5223 0.079 Uiso 1 1 calc R A . H13B H 0.1934 0.4418 0.5452 0.079 Uiso 1 1 calc R . . C14 C 0.3242(10) 0.5406(4) 0.5813(3) 0.0619(16) Uani 1 1 d U A . H14 H 0.2476 0.5439 0.6140 0.074 Uiso 1 1 calc R . . C15 C 0.616(3) 0.255(2) 0.3960(14) 0.074(5) Uani 0.50 1 d PU A 1 H15A H 0.7334 0.2735 0.4055 0.111 Uiso 0.50 1 calc PR A 1 H15B H 0.6244 0.2116 0.3694 0.111 Uiso 0.50 1 calc PR A 1 H15C H 0.5573 0.2355 0.4287 0.111 Uiso 0.50 1 calc PR A 1 C15A C 0.562(3) 0.2455(19) 0.3957(14) 0.067(5) Uani 0.50 1 d PU A 2 H15D H 0.6639 0.2533 0.4192 0.101 Uiso 0.50 1 calc PR A 2 H15E H 0.5921 0.2080 0.3665 0.101 Uiso 0.50 1 calc PR A 2 H15F H 0.4662 0.2236 0.4172 0.101 Uiso 0.50 1 calc PR A 2 C16 C 0.6089(12) 0.3534(5) 0.3186(3) 0.0711(19) Uani 1 1 d U A . C18 C 0.4254(11) 0.3368(4) 0.5047(3) 0.074(2) Uani 1 1 d U A . H18A H 0.3921 0.3574 0.5405 0.111 Uiso 1 1 calc R . . H18B H 0.5514 0.3280 0.5037 0.111 Uiso 1 1 calc R . . H18C H 0.3652 0.2860 0.4980 0.111 Uiso 1 1 calc R . . C19 C 0.6055(9) 0.4942(4) 0.5525(3) 0.0589(16) Uani 1 1 d U A . H19 H 0.7161 0.4694 0.5556 0.071 Uiso 1 1 calc R . . C20 C 0.4980(10) 0.5009(4) 0.5949(3) 0.0593(16) Uani 1 1 d U . . C21 C 0.563(2) 0.4697(16) 0.6542(11) 0.062(3) Uani 0.50 1 d PU A 1 H21 H 0.5235 0.5106 0.6812 0.074 Uiso 0.50 1 calc PR A 1 C22 C 0.457(3) 0.3912(16) 0.6667(12) 0.079(5) Uani 0.50 1 d PU A 1 H22A H 0.4687 0.3776 0.7052 0.119 Uiso 0.50 1 calc PR A 1 H22B H 0.5019 0.3471 0.6445 0.119 Uiso 0.50 1 calc PR A 1 H22C H 0.3339 0.4000 0.6581 0.119 Uiso 0.50 1 calc PR A 1 C23 C 0.761(2) 0.4625(16) 0.6612(11) 0.077(4) Uani 0.50 1 d PU A 1 H23A H 0.8040 0.4168 0.6400 0.116 Uiso 0.50 1 calc PR A 1 H23B H 0.7891 0.4543 0.6996 0.116 Uiso 0.50 1 calc PR A 1 H23C H 0.8173 0.5116 0.6483 0.116 Uiso 0.50 1 calc PR A 1 C21A C 0.500(2) 0.4728(16) 0.6548(10) 0.061(3) Uani 0.50 1 d PDU A 2 H21A H 0.4680 0.5195 0.6782 0.074 Uiso 0.50 1 calc PR A 2 C22A C 0.374(3) 0.4014(15) 0.6690(11) 0.073(5) Uani 0.50 1 d PU A 2 H22D H 0.3980 0.3561 0.6449 0.110 Uiso 0.50 1 calc PR A 2 H22E H 0.2532 0.4188 0.6642 0.110 Uiso 0.50 1 calc PR A 2 H22F H 0.3922 0.3851 0.7068 0.110 Uiso 0.50 1 calc PR A 2 C23A C 0.695(2) 0.4484(16) 0.6690(11) 0.077(4) Uani 0.50 1 d PDU A 2 H23D H 0.7675 0.4965 0.6698 0.116 Uiso 0.50 1 calc PR A 2 H23E H 0.7385 0.4115 0.6413 0.116 Uiso 0.50 1 calc PR A 2 H23F H 0.6975 0.4223 0.7046 0.116 Uiso 0.50 1 calc PR A 2 C24 C 0.4757(10) 0.6731(4) 0.6019(3) 0.0660(17) Uani 1 1 d U . . C25 C 0.6524(11) 0.6749(5) 0.5235(3) 0.0675(17) Uani 1 1 d U . . C26 C 0.7601(11) 0.7513(5) 0.6086(3) 0.0776(18) Uani 1 1 d U . . C27 C 0.9248(12) 0.7175(6) 0.6188(4) 0.090(2) Uani 1 1 d U B 1 H27 H 0.9541 0.6667 0.6042 0.108 Uiso 1 1 calc R B 1 C28 C 1.0452(13) 0.7596(7) 0.6509(4) 0.105(2) Uani 1 1 d U B 1 H28 H 1.1584 0.7383 0.6559 0.126 Uiso 1 1 calc R B 1 C29 C 1.0023(13) 0.8309(6) 0.6749(4) 0.101(2) Uani 1 1 d U B 1 H29 H 1.0840 0.8575 0.6975 0.121 Uiso 1 1 calc R B 1 C30 C 0.8355(13) 0.8652(6) 0.6660(4) 0.086(2) Uani 1 1 d U B 1 C31 C 0.7785(14) 0.9375(6) 0.6928(4) 0.092(2) Uani 1 1 d U B 1 H31 H 0.8596 0.9649 0.7151 0.111 Uiso 1 1 calc R B 1 C32 C 0.6206(15) 0.9679(5) 0.6881(4) 0.090(2) Uani 1 1 d U B 1 H32 H 0.5888 1.0146 0.7077 0.108 Uiso 1 1 calc R B 1 C33 C 0.4992(13) 0.9296(5) 0.6532(3) 0.089(2) Uani 1 1 d U B 1 H33 H 0.3875 0.9529 0.6488 0.107 Uiso 1 1 calc R B 1 C34 C 0.5375(12) 0.8591(5) 0.6253(3) 0.081(2) Uani 1 1 d U . . H34 H 0.4533 0.8344 0.6026 0.097 Uiso 1 1 calc R B 1 C35 C 0.7069(11) 0.8247(5) 0.6317(3) 0.0748(18) Uani 1 1 d U B . O1 O 0.758(2) 0.3104(12) 0.3068(9) 0.075(2) Uani 0.50 1 d PU A 1 O2 O 0.6295(19) 0.4238(9) 0.3010(6) 0.079(4) Uani 0.50 1 d PU A 1 C17 C 0.869(3) 0.3284(17) 0.2587(10) 0.081(4) Uani 0.50 1 d PU A 1 H17A H 0.8298 0.3781 0.2416 0.122 Uiso 0.50 1 calc PR A 1 H17B H 0.8609 0.2843 0.2325 0.122 Uiso 0.50 1 calc PR A 1 H17C H 0.9906 0.3344 0.2703 0.122 Uiso 0.50 1 calc PR A 1 C17A C 0.808(3) 0.3103(17) 0.2533(10) 0.081(4) Uani 0.50 1 d PDU A 2 H17D H 0.8396 0.3671 0.2519 0.122 Uiso 0.50 1 calc PR A 2 H17E H 0.7359 0.2970 0.2217 0.122 Uiso 0.50 1 calc PR A 2 H17F H 0.9136 0.2776 0.2529 0.122 Uiso 0.50 1 calc PR A 2 O1A O 0.710(2) 0.2943(12) 0.3032(8) 0.075(2) Uani 0.50 1 d PDU A 2 O2A O 0.5458(19) 0.4039(9) 0.2857(6) 0.082(4) Uani 0.50 1 d PU A 2 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 O3 0.068(3) 0.065(3) 0.070(3) 0.001(3) 0.010(3) -0.002(3) O4 0.103(4) 0.091(4) 0.081(3) -0.002(3) 0.033(3) -0.038(4) N1 0.065(3) 0.067(3) 0.078(3) 0.006(3) 0.009(3) -0.006(3) C1 0.055(3) 0.059(3) 0.069(3) 0.006(3) 0.002(3) 0.002(3) C2 0.058(4) 0.057(3) 0.058(3) 0.009(3) 0.014(3) 0.001(3) C3 0.052(3) 0.062(3) 0.054(3) 0.005(3) 0.006(3) 0.003(3) C4 0.062(4) 0.058(4) 0.066(4) 0.005(3) 0.011(3) -0.002(3) C5 0.049(4) 0.064(4) 0.069(4) 0.005(3) 0.011(3) -0.002(3) C6 0.059(4) 0.054(3) 0.063(3) 0.013(3) 0.000(3) 0.003(3) C7 0.072(4) 0.066(4) 0.064(4) 0.001(3) 0.004(3) -0.001(4) C8 0.085(4) 0.064(4) 0.075(4) -0.010(4) -0.001(4) 0.001(4) C9 0.066(4) 0.070(4) 0.083(4) -0.008(4) 0.004(4) -0.007(4) C10 0.076(4) 0.075(4) 0.068(4) 0.002(3) 0.002(4) 0.000(4) C11 0.056(3) 0.064(3) 0.062(3) 0.006(3) 0.002(3) 0.000(3) C12 0.053(3) 0.052(3) 0.055(3) 0.010(3) 0.009(3) 0.002(3) C13 0.061(4) 0.067(4) 0.068(3) 0.000(3) 0.010(3) -0.006(3) C14 0.056(3) 0.070(3) 0.059(3) -0.008(3) 0.009(3) -0.005(3) C15 0.084(9) 0.061(8) 0.077(8) 0.010(7) 0.011(9) -0.003(8) C15A 0.057(9) 0.060(9) 0.084(8) 0.006(8) -0.002(9) 0.014(8) C16 0.078(5) 0.062(4) 0.073(4) 0.002(4) 0.003(4) 0.007(4) C18 0.085(5) 0.056(4) 0.081(5) 0.008(4) 0.004(4) 0.004(4) C19 0.051(3) 0.060(3) 0.066(3) 0.000(3) -0.001(3) 0.002(3) C20 0.064(3) 0.054(3) 0.060(3) -0.001(3) 0.001(3) -0.006(3) C21 0.057(6) 0.063(5) 0.064(5) -0.002(5) 0.005(6) 0.002(6) C22 0.070(11) 0.076(10) 0.092(9) 0.013(8) 0.011(10) -0.004(10) C23 0.075(9) 0.087(7) 0.070(7) 0.020(5) -0.004(8) -0.011(8) C21A 0.057(6) 0.064(6) 0.064(5) 0.000(5) 0.004(6) 0.000(6) C22A 0.077(10) 0.064(9) 0.078(9) -0.001(7) 0.020(10) 0.010(10) C23A 0.075(9) 0.087(7) 0.070(7) 0.020(5) -0.004(8) -0.011(8) C24 0.065(4) 0.065(3) 0.068(3) 0.003(3) 0.005(3) 0.004(3) C25 0.070(4) 0.064(4) 0.069(4) 0.007(3) 0.010(3) -0.009(4) C26 0.070(4) 0.085(4) 0.077(4) 0.008(3) 0.014(3) -0.005(4) C27 0.071(4) 0.097(5) 0.102(4) -0.010(4) 0.007(4) 0.005(4) C28 0.061(5) 0.136(6) 0.117(5) -0.003(5) 0.005(4) 0.000(5) C29 0.083(5) 0.116(5) 0.104(5) -0.004(4) 0.006(4) -0.024(5) C30 0.082(4) 0.092(4) 0.083(4) 0.000(4) 0.008(4) -0.014(4) C31 0.089(5) 0.096(5) 0.092(5) 0.011(4) -0.003(4) -0.029(5) C32 0.113(6) 0.068(5) 0.089(5) 0.009(4) 0.004(5) -0.023(5) C33 0.104(5) 0.073(5) 0.092(5) 0.006(4) -0.024(5) 0.005(5) C34 0.085(4) 0.072(4) 0.085(4) 0.012(4) -0.009(4) -0.004(4) C35 0.068(4) 0.078(4) 0.078(4) 0.002(3) 0.004(3) -0.006(4) O1 0.075(5) 0.072(5) 0.077(3) -0.004(4) 0.008(4) -0.011(4) O2 0.081(8) 0.076(8) 0.081(7) 0.005(6) 0.019(6) 0.000(7) C17 0.089(10) 0.081(9) 0.073(6) -0.007(6) 0.018(7) -0.009(8) C17A 0.089(10) 0.081(9) 0.073(6) -0.007(6) 0.018(7) -0.009(8) O1A 0.075(5) 0.072(5) 0.077(3) -0.004(4) 0.008(4) -0.011(4) O2A 0.089(8) 0.073(7) 0.085(7) 0.016(6) 0.000(7) 0.005(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C24 1.231(8) . ? O4 C25 1.192(8) . ? N1 C24 1.385(9) . ? N1 C25 1.391(9) . ? N1 C26 1.474(10) . ? C1 H1 0.9800 . ? C1 C2 1.526(9) . ? C1 C14 1.550(10) . ? C1 C24 1.499(9) . ? C2 H2 0.9800 . ? C2 C3 1.574(9) . ? C2 C25 1.509(10) . ? C3 C4 1.539(9) . ? C3 C12 1.559(9) . ? C3 C19 1.511(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C5 1.526(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C6 1.521(9) . ? C6 H6 0.9800 . ? C6 C7 1.542(9) . ? C6 C11 1.561(9) . ? C7 C8 1.532(10) . ? C7 C15 1.60(3) . ? C7 C15A 1.56(3) . ? C7 C16 1.518(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.526(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.540(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.568(10) . ? C11 C12 1.555(9) . ? C11 C18 1.571(9) . ? C12 H12 0.9800 . ? C12 C13 1.558(9) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.545(9) . ? C14 H14 0.9800 . ? C14 C20 1.498(10) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C15A H15D 0.9600 . ? C15A H15E 0.9600 . ? C15A H15F 0.9600 . ? C16 O1 1.36(2) . ? C16 O2 1.236(16) . ? C16 O1A 1.29(2) . ? C16 O2A 1.239(16) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19 0.9300 . ? C19 C20 1.310(9) . ? C20 C21 1.60(3) . ? C20 C21A 1.52(3) . ? C21 H21 0.9800 . ? C21 C22 1.54(3) . ? C21 C23 1.51(2) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C21A H21A 0.9800 . ? C21A C22A 1.55(3) . ? C21A C23A 1.554(9) . ? C22A H22D 0.9600 . ? C22A H22E 0.9600 . ? C22A H22F 0.9600 . ? C23A H23D 0.9600 . ? C23A H23E 0.9600 . ? C23A H23F 0.9600 . ? C26 C27 1.380(11) . ? C26 C35 1.384(11) . ? C27 H27 0.9300 . ? C27 C28 1.377(12) . ? C28 H28 0.9300 . ? C28 C29 1.342(12) . ? C29 H29 0.9300 . ? C29 C30 1.393(13) . ? C30 C31 1.415(12) . ? C30 C35 1.435(11) . ? C31 H31 0.9300 . ? C31 C32 1.294(12) . ? C32 H32 0.9300 . ? C32 C33 1.392(11) . ? C33 H33 0.9300 . ? C33 C34 1.368(10) . ? C34 H34 0.9300 . ? C34 C35 1.403(11) . ? O1 C17 1.461(19) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17A H17D 0.9600 . ? C17A H17E 0.9600 . ? C17A H17F 0.9600 . ? C17A O1A 1.437(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C24 N1 C25 112.9(7) . . ? C24 N1 C26 122.0(6) . . ? C25 N1 C26 124.6(6) . . ? C2 C1 H1 110.2 . . ? C2 C1 C14 111.2(6) . . ? C14 C1 H1 110.2 . . ? C24 C1 H1 110.2 . . ? C24 C1 C2 104.6(6) . . ? C24 C1 C14 110.2(6) . . ? C1 C2 H2 109.2 . . ? C1 C2 C3 108.3(5) . . ? C3 C2 H2 109.2 . . ? C25 C2 C1 105.5(6) . . ? C25 C2 H2 109.2 . . ? C25 C2 C3 115.3(6) . . ? C4 C3 C2 110.7(5) . . ? C4 C3 C12 111.0(5) . . ? C12 C3 C2 105.5(5) . . ? C19 C3 C2 106.7(5) . . ? C19 C3 C4 113.3(6) . . ? C19 C3 C12 109.3(5) . . ? C3 C4 H4A 109.2 . . ? C3 C4 H4B 109.2 . . ? C3 C4 C5 112.1(6) . . ? H4A C4 H4B 107.9 . . ? C5 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C6 C5 C4 110.7(6) . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? C5 C6 H6 104.6 . . ? C5 C6 C7 115.6(6) . . ? C5 C6 C11 109.5(5) . . ? C7 C6 H6 104.6 . . ? C7 C6 C11 116.5(6) . . ? C11 C6 H6 104.6 . . ? C6 C7 C15A 117.3(13) . . ? C8 C7 C6 108.4(6) . . ? C8 C7 C15A 103.0(10) . . ? C15 C7 C6 111.7(13) . . ? C15 C7 C8 118.4(11) . . ? C15 C7 C15A 15.7(15) . . ? C15 C7 C16 104.6(12) . . ? C16 C7 C6 107.1(6) . . ? C16 C7 C8 105.9(6) . . ? C16 C7 C15A 114.4(13) . . ? C7 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C9 C8 C7 112.9(6) . . ? C9 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C10 C9 C8 110.8(6) . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C9 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C9 C10 C11 112.6(6) . . ? H10A C10 H10B 107.8 . . ? C11 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C6 C11 C10 108.1(5) . . ? C6 C11 C12 107.2(5) . . ? C6 C11 C18 114.0(6) . . ? C10 C11 C18 109.3(6) . . ? C12 C11 C10 106.5(6) . . ? C12 C11 C18 111.5(5) . . ? C3 C12 C11 115.4(5) . . ? C3 C12 H12 106.0 . . ? C3 C12 C13 109.1(5) . . ? C11 C12 H12 106.0 . . ? C11 C12 C13 113.8(5) . . ? C13 C12 H12 106.0 . . ? C12 C13 H13A 109.8 . . ? C12 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C14 C13 C12 109.5(5) . . ? C14 C13 H13A 109.8 . . ? C14 C13 H13B 109.8 . . ? C1 C14 H14 111.2 . . ? C13 C14 C1 106.3(6) . . ? C13 C14 H14 111.2 . . ? C20 C14 C1 105.6(6) . . ? C20 C14 C13 111.2(6) . . ? C20 C14 H14 111.2 . . ? C7 C15 H15A 109.5 . . ? C7 C15 H15B 109.5 . . ? C7 C15 H15C 109.5 . . ? C7 C15A H15D 109.5 . . ? C7 C15A H15E 109.5 . . ? C7 C15A H15F 109.5 . . ? H15D C15A H15E 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? O1 C16 C7 117.4(11) . . ? O2 C16 C7 126.1(10) . . ? O2 C16 O1 107.8(13) . . ? O1A C16 C7 110.0(11) . . ? O1A C16 O1 19.7(12) . . ? O1A C16 O2 121.8(12) . . ? O2A C16 C7 120.1(10) . . ? O2A C16 O1 121.9(13) . . ? O2A C16 O2 37.7(8) . . ? O2A C16 O1A 122.9(14) . . ? C11 C18 H18A 109.5 . . ? C11 C18 H18B 109.5 . . ? C11 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C3 C19 H19 121.9 . . ? C20 C19 C3 116.2(6) . . ? C20 C19 H19 121.9 . . ? C14 C20 C21 127.2(9) . . ? C14 C20 C21A 110.6(8) . . ? C19 C20 C14 113.9(6) . . ? C19 C20 C21 118.9(9) . . ? C19 C20 C21A 135.4(9) . . ? C21 C20 C21A 17.3(9) . . ? C20 C21 H21 106.4 . . ? C20 C21 C22 106.3(17) . . ? C20 C21 C23 115.4(16) . . ? C22 C21 H21 106.4 . . ? C23 C21 H21 106.4 . . ? C23 C21 C22 115.3(19) . . ? C20 C21A H21A 107.9 . . ? C22A C21A C20 115.7(17) . . ? C22A C21A H21A 107.9 . . ? C22A C21A C23A 109.7(17) . . ? C23A C21A C20 107.4(15) . . ? C23A C21A H21A 107.9 . . ? C21A C22A H22D 109.5 . . ? C21A C22A H22E 109.5 . . ? C21A C22A H22F 109.5 . . ? H22D C22A H22E 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? C21A C23A H23D 109.5 . . ? C21A C23A H23E 109.5 . . ? C21A C23A H23F 109.5 . . ? H23D C23A H23E 109.5 . . ? H23D C23A H23F 109.5 . . ? H23E C23A H23F 109.5 . . ? O3 C24 N1 124.0(7) . . ? O3 C24 C1 127.2(7) . . ? N1 C24 C1 108.6(6) . . ? O4 C25 N1 123.5(8) . . ? O4 C25 C2 128.8(7) . . ? N1 C25 C2 107.7(6) . . ? C27 C26 N1 118.9(8) . . ? C27 C26 C35 122.5(9) . . ? C35 C26 N1 118.2(8) . . ? C26 C27 H27 120.3 . . ? C26 C27 C28 119.4(9) . . ? C28 C27 H27 120.3 . . ? C27 C28 H28 119.4 . . ? C29 C28 C27 121.3(10) . . ? C29 C28 H28 119.4 . . ? C28 C29 H29 120.0 . . ? C28 C29 C30 120.0(10) . . ? C30 C29 H29 120.0 . . ? C29 C30 C31 122.7(10) . . ? C29 C30 C35 120.8(9) . . ? C31 C30 C35 116.4(9) . . ? C30 C31 H31 118.0 . . ? C32 C31 C30 124.1(10) . . ? C32 C31 H31 118.0 . . ? C31 C32 H32 120.5 . . ? C31 C32 C33 118.9(10) . . ? C33 C32 H32 120.5 . . ? C32 C33 H33 118.7 . . ? C34 C33 C32 122.6(9) . . ? C34 C33 H33 118.7 . . ? C33 C34 H34 120.8 . . ? C33 C34 C35 118.4(9) . . ? C35 C34 H34 120.8 . . ? C26 C35 C30 115.9(8) . . ? C26 C35 C34 124.5(8) . . ? C34 C35 C30 119.5(8) . . ? C16 O1 C17 122.5(18) . . ? H17D C17A H17E 109.5 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? O1A C17A H17D 109.5 . . ? O1A C17A H17E 109.5 . . ? O1A C17A H17F 109.5 . . ? C16 O1A C17A 114.1(18) . . ? 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 N1 C26 C27 C28 -176.1(8) . . . . ? N1 C26 C35 C30 174.5(7) . . . . ? N1 C26 C35 C34 -3.1(12) . . . . ? C1 C2 C3 C4 -176.2(6) . . . . ? C1 C2 C3 C12 63.7(7) . . . . ? C1 C2 C3 C19 -52.5(7) . . . . ? C1 C2 C25 O4 -174.9(8) . . . . ? C1 C2 C25 N1 3.5(8) . . . . ? C1 C14 C20 C19 -59.8(8) . . . . ? C1 C14 C20 C21 118.5(13) . . . . ? C1 C14 C20 C21A 124.2(12) . . . . ? C2 C1 C14 C13 -60.5(7) . . . . ? C2 C1 C14 C20 57.7(7) . . . . ? C2 C1 C24 O3 -166.9(7) . . . . ? C2 C1 C24 N1 8.8(7) . . . . ? C2 C3 C4 C5 -165.4(6) . . . . ? C2 C3 C12 C11 168.3(5) . . . . ? C2 C3 C12 C13 -62.2(7) . . . . ? C2 C3 C19 C20 56.8(8) . . . . ? C3 C2 C25 O4 65.7(10) . . . . ? C3 C2 C25 N1 -115.9(6) . . . . ? C3 C4 C5 C6 58.2(8) . . . . ? C3 C12 C13 C14 -0.2(8) . . . . ? C3 C19 C20 C14 1.7(9) . . . . ? C3 C19 C20 C21 -176.8(12) . . . . ? C3 C19 C20 C21A 176.4(15) . . . . ? C4 C3 C12 C11 48.4(8) . . . . ? C4 C3 C12 C13 177.9(5) . . . . ? C4 C3 C19 C20 178.9(6) . . . . ? C4 C5 C6 C7 161.6(5) . . . . ? C4 C5 C6 C11 -64.4(7) . . . . ? C5 C6 C7 C8 -175.7(6) . . . . ? C5 C6 C7 C15 52.1(13) . . . . ? C5 C6 C7 C15A 68.3(12) . . . . ? C5 C6 C7 C16 -61.9(8) . . . . ? C5 C6 C11 C10 174.6(6) . . . . ? C5 C6 C11 C12 60.2(7) . . . . ? C5 C6 C11 C18 -63.7(8) . . . . ? C6 C7 C8 C9 -55.2(8) . . . . ? C6 C7 C16 O1 119.0(10) . . . . ? C6 C7 C16 O2 -24.5(15) . . . . ? C6 C7 C16 O1A 139.0(10) . . . . ? C6 C7 C16 O2A -69.4(12) . . . . ? C6 C11 C12 C3 -53.5(7) . . . . ? C6 C11 C12 C13 179.3(5) . . . . ? C7 C6 C11 C10 -51.9(8) . . . . ? C7 C6 C11 C12 -166.3(6) . . . . ? C7 C6 C11 C18 69.8(8) . . . . ? C7 C8 C9 C10 58.4(9) . . . . ? C7 C16 O1 C17 -179.5(13) . . . . ? C7 C16 O1A C17A 177.6(13) . . . . ? C8 C7 C16 O1 -125.5(10) . . . . ? C8 C7 C16 O2 91.0(13) . . . . ? C8 C7 C16 O1A -105.5(11) . . . . ? C8 C7 C16 O2A 46.1(12) . . . . ? C8 C9 C10 C11 -56.5(8) . . . . ? C9 C10 C11 C6 51.7(8) . . . . ? C9 C10 C11 C12 166.5(6) . . . . ? C9 C10 C11 C18 -72.9(7) . . . . ? C10 C11 C12 C3 -169.0(5) . . . . ? C10 C11 C12 C13 63.8(7) . . . . ? C11 C6 C7 C8 53.6(8) . . . . ? C11 C6 C7 C15 -78.6(12) . . . . ? C11 C6 C7 C15A -62.4(12) . . . . ? C11 C6 C7 C16 167.4(6) . . . . ? C11 C12 C13 C14 130.1(6) . . . . ? C12 C3 C4 C5 -48.6(8) . . . . ? C12 C3 C19 C20 -56.8(8) . . . . ? C12 C13 C14 C1 61.4(7) . . . . ? C12 C13 C14 C20 -53.0(8) . . . . ? C13 C14 C20 C19 55.0(8) . . . . ? C13 C14 C20 C21 -126.7(13) . . . . ? C13 C14 C20 C21A -121.0(12) . . . . ? C14 C1 C2 C3 -2.3(8) . . . . ? C14 C1 C2 C25 -126.3(6) . . . . ? C14 C1 C24 O3 -47.3(10) . . . . ? C14 C1 C24 N1 128.5(6) . . . . ? C14 C20 C21 C22 73.2(19) . . . . ? C14 C20 C21 C23 -157.5(15) . . . . ? C14 C20 C21A C22A 68.1(18) . . . . ? C14 C20 C21A C23A -169.0(14) . . . . ? C15 C7 C8 C9 73.3(16) . . . . ? C15 C7 C16 O1 0.3(15) . . . . ? C15 C7 C16 O2 -143.2(17) . . . . ? C15 C7 C16 O1A 20.3(16) . . . . ? C15 C7 C16 O2A 171.9(15) . . . . ? C15A C7 C8 C9 69.7(14) . . . . ? C15A C7 C16 O1 -12.8(17) . . . . ? C15A C7 C16 O2 -156.3(16) . . . . ? C15A C7 C16 O1A 7.2(16) . . . . ? C15A C7 C16 O2A 158.8(15) . . . . ? C16 C7 C8 C9 -169.8(6) . . . . ? C18 C11 C12 C3 71.8(7) . . . . ? C18 C11 C12 C13 -55.3(8) . . . . ? C19 C3 C4 C5 74.8(7) . . . . ? C19 C3 C12 C11 -77.3(7) . . . . ? C19 C3 C12 C13 52.2(7) . . . . ? C19 C20 C21 C22 -108.5(13) . . . . ? C19 C20 C21 C23 21(2) . . . . ? C19 C20 C21A C22A -106.7(15) . . . . ? C19 C20 C21A C23A 16(3) . . . . ? C21 C20 C21A C22A -127(7) . . . . ? C21 C20 C21A C23A -4(5) . . . . ? C21A C20 C21 C22 55(6) . . . . ? C21A C20 C21 C23 -176(8) . . . . ? C24 N1 C25 O4 -179.3(7) . . . . ? C24 N1 C25 C2 2.1(8) . . . . ? C24 N1 C26 C27 111.4(9) . . . . ? C24 N1 C26 C35 -61.7(10) . . . . ? C24 C1 C2 C3 116.6(6) . . . . ? C24 C1 C2 C25 -7.3(7) . . . . ? C24 C1 C14 C13 -176.0(6) . . . . ? C24 C1 C14 C20 -57.8(7) . . . . ? C25 N1 C24 O3 168.8(7) . . . . ? C25 N1 C24 C1 -7.1(8) . . . . ? C25 N1 C26 C27 -60.0(11) . . . . ? C25 N1 C26 C35 126.9(8) . . . . ? C25 C2 C3 C4 -58.3(7) . . . . ? C25 C2 C3 C12 -178.4(5) . . . . ? C25 C2 C3 C19 65.4(7) . . . . ? C26 N1 C24 O3 -3.5(12) . . . . ? C26 N1 C24 C1 -179.4(6) . . . . ? C26 N1 C25 O4 -7.2(12) . . . . ? C26 N1 C25 C2 174.2(7) . . . . ? C26 C27 C28 C29 3.7(15) . . . . ? C27 C26 C35 C30 1.6(12) . . . . ? C27 C26 C35 C34 -176.0(8) . . . . ? C27 C28 C29 C30 -2.4(15) . . . . ? C28 C29 C30 C31 176.0(9) . . . . ? C28 C29 C30 C35 0.7(14) . . . . ? C29 C30 C31 C32 -175.4(9) . . . . ? C29 C30 C35 C26 -0.3(12) . . . . ? C29 C30 C35 C34 177.4(8) . . . . ? C30 C31 C32 C33 -2.4(14) . . . . ? C31 C30 C35 C26 -175.9(7) . . . . ? C31 C30 C35 C34 1.8(12) . . . . ? C31 C32 C33 C34 2.7(13) . . . . ? C32 C33 C34 C35 -0.8(12) . . . . ? C33 C34 C35 C26 176.0(8) . . . . ? C33 C34 C35 C30 -1.5(12) . . . . ? C35 C26 C27 C28 -3.3(13) . . . . ? C35 C30 C31 C32 0.2(13) . . . . ? O1 C16 O1A C17A -67(5) . . . . ? O2 C16 O1 C17 -29.9(19) . . . . ? O2 C16 O1A C17A -18(2) . . . . ? O1A C16 O1 C17 108(6) . . . . ? O2A C16 O1 C17 9(2) . . . . ? O2A C16 O1A C17A 27(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 948184' ####################################################################### # # 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_whs-zyt-5f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H40 N2 O4' _chemical_formula_weight 540.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.54394(18) _cell_length_b 14.0556(4) _cell_length_c 24.3015(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2918.37(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36456 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5974 _reflns_number_gt 5434 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.5494P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(14) _refine_ls_number_reflns 5974 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.9495(4) 0.36923(18) -0.02042(10) 0.1368(11) Uani 1 1 d . . . O2 O 0.8854(3) 0.35903(14) 0.06587(9) 0.0992(7) Uani 1 1 d . . . O3 O 1.30550(18) 0.71098(13) 0.19948(8) 0.0728(5) Uani 1 1 d . . . O4 O 0.9958(2) 0.92417(13) 0.28818(7) 0.0724(5) Uani 1 1 d . . . N1 N 1.3741(2) 0.76487(14) 0.32668(8) 0.0607(5) Uani 1 1 d . . . N2 N 1.1785(2) 0.83113(12) 0.24505(7) 0.0531(4) Uani 1 1 d . . . C0AA C 0.8836(3) 0.40201(16) 0.01789(10) 0.0640(6) Uani 1 1 d . . . C1 C 1.4718(3) 0.7336(2) 0.36451(11) 0.0796(7) Uani 1 1 d . . . H1 H 1.4453 0.6776 0.3826 0.095 Uiso 1 1 calc R . . C2 C 1.6109(3) 0.7772(2) 0.37962(12) 0.0825(8) Uani 1 1 d . . . H2 H 1.6744 0.7505 0.4066 0.099 Uiso 1 1 calc R . . C3 C 1.6526(3) 0.8592(2) 0.35441(10) 0.0700(6) Uani 1 1 d . . . H3 H 1.7459 0.8893 0.3636 0.084 Uiso 1 1 calc R . . C4 C 1.5533(2) 0.89838(15) 0.31418(8) 0.0532(5) Uani 1 1 d . . . C5 C 1.5855(3) 0.98556(16) 0.28715(9) 0.0578(5) Uani 1 1 d . . . H5 H 1.6753 1.0197 0.2961 0.069 Uiso 1 1 calc R . . C6 C 1.4872(3) 1.01909(17) 0.24873(11) 0.0669(6) Uani 1 1 d . . . H6 H 1.5086 1.0768 0.2316 0.080 Uiso 1 1 calc R . . C7 C 1.3494(3) 0.96696(16) 0.23383(10) 0.0615(6) Uani 1 1 d . . . H7 H 1.2828 0.9897 0.2066 0.074 Uiso 1 1 calc R . . C8 C 1.3177(2) 0.88436(15) 0.25994(9) 0.0528(5) Uani 1 1 d . . . C9 C 1.4151(2) 0.84724(15) 0.30102(8) 0.0497(4) Uani 1 1 d . . . C10 C 1.1854(2) 0.74601(15) 0.21497(8) 0.0511(5) Uani 1 1 d . . . C11 C 1.0191(2) 0.71051(14) 0.20657(7) 0.0439(4) Uani 1 1 d . . . H11 H 1.0059 0.6489 0.2248 0.053 Uiso 1 1 calc R . . C12 C 0.9158(2) 0.78524(14) 0.23481(8) 0.0465(4) Uani 1 1 d . . . H12 H 0.8522 0.7552 0.2635 0.056 Uiso 1 1 calc R . . C13 C 1.0280(2) 0.85623(16) 0.26045(8) 0.0523(5) Uani 1 1 d . . . C14 C 0.8078(2) 0.83261(14) 0.19108(8) 0.0461(4) Uani 1 1 d . . . H14 H 0.7467 0.8846 0.2072 0.055 Uiso 1 1 calc R . . C15 C 0.7002(2) 0.75332(15) 0.16885(8) 0.0489(4) Uani 1 1 d . . . H15A H 0.6296 0.7796 0.1416 0.059 Uiso 1 1 calc R . . H15B H 0.6377 0.7277 0.1987 0.059 Uiso 1 1 calc R . . C16 C 0.7985(2) 0.67258(12) 0.14258(7) 0.0387(4) Uani 1 1 d . . . H16 H 0.7877 0.6174 0.1669 0.046 Uiso 1 1 calc R . . C17 C 0.97616(19) 0.70101(12) 0.14389(7) 0.0369(4) Uani 1 1 d . . . C18 C 0.9933(2) 0.79962(12) 0.12070(7) 0.0398(4) Uani 1 1 d . . . H18 H 1.0600 0.8122 0.0913 0.048 Uiso 1 1 calc R . . C19 C 0.9089(2) 0.86797(13) 0.14409(8) 0.0435(4) Uani 1 1 d . . . C20 C 0.8997(3) 0.96990(14) 0.12387(9) 0.0582(5) Uani 1 1 d . . . H20 H 0.9825 0.9787 0.0964 0.070 Uiso 1 1 calc R . . C21 C 0.9267(4) 1.04284(16) 0.16972(12) 0.0814(8) Uani 1 1 d . . . H21A H 0.8507 1.0335 0.1983 0.122 Uiso 1 1 calc R . . H21B H 0.9163 1.1059 0.1550 0.122 Uiso 1 1 calc R . . H21C H 1.0300 1.0348 0.1846 0.122 Uiso 1 1 calc R . . C22 C 0.7444(4) 0.9889(2) 0.09573(12) 0.0846(8) Uani 1 1 d . . . H22A H 0.7311 0.9452 0.0658 0.127 Uiso 1 1 calc R . . H22B H 0.7431 1.0529 0.0819 0.127 Uiso 1 1 calc R . . H22C H 0.6608 0.9807 0.1217 0.127 Uiso 1 1 calc R . . C23 C 0.7389(2) 0.64014(13) 0.08483(7) 0.0402(4) Uani 1 1 d . . . C24 C 0.5710(2) 0.60202(17) 0.09170(9) 0.0558(5) Uani 1 1 d . . . H24A H 0.5679 0.5598 0.1233 0.067 Uiso 1 1 calc R . . H24B H 0.5014 0.6550 0.0992 0.067 Uiso 1 1 calc R . . C25 C 0.5111(3) 0.54836(18) 0.04115(10) 0.0641(6) Uani 1 1 d . . . H25A H 0.4059 0.5254 0.0482 0.077 Uiso 1 1 calc R . . H25B H 0.5068 0.5914 0.0100 0.077 Uiso 1 1 calc R . . C26 C 0.6158(3) 0.46556(17) 0.02755(10) 0.0629(6) Uani 1 1 d . . . H26A H 0.5765 0.4346 -0.0053 0.075 Uiso 1 1 calc R . . H26B H 0.6108 0.4198 0.0574 0.075 Uiso 1 1 calc R . . C27 C 0.7902(2) 0.49375(15) 0.01800(8) 0.0504(5) Uani 1 1 d . . . C28 C 0.8115(3) 0.53995(19) -0.03853(8) 0.0651(6) Uani 1 1 d . . . H28A H 0.7495 0.5968 -0.0405 0.098 Uiso 1 1 calc R . . H28B H 0.7785 0.4964 -0.0666 0.098 Uiso 1 1 calc R . . H28C H 0.9198 0.5556 -0.0439 0.098 Uiso 1 1 calc R . . C29 C 0.8472(2) 0.55590(13) 0.06762(7) 0.0409(4) Uani 1 1 d . . . H29 H 0.8475 0.5128 0.0993 0.049 Uiso 1 1 calc R . . C30 C 1.0161(2) 0.58923(13) 0.06179(8) 0.0447(4) Uani 1 1 d . . . H30A H 1.0215 0.6400 0.0348 0.054 Uiso 1 1 calc R . . H30B H 1.0804 0.5370 0.0488 0.054 Uiso 1 1 calc R . . C31 C 1.0787(2) 0.62490(13) 0.11707(8) 0.0432(4) Uani 1 1 d . . . H31A H 1.0878 0.5713 0.1420 0.052 Uiso 1 1 calc R . . H31B H 1.1828 0.6507 0.1116 0.052 Uiso 1 1 calc R . . C32 C 0.7353(3) 0.72251(15) 0.04290(8) 0.0518(5) Uani 1 1 d . . . H32A H 0.6802 0.7756 0.0584 0.078 Uiso 1 1 calc R . . H32B H 0.6831 0.7020 0.0100 0.078 Uiso 1 1 calc R . . H32C H 0.8405 0.7412 0.0341 0.078 Uiso 1 1 calc R . . C33 C 0.9596(5) 0.2680(2) 0.06906(19) 0.1268(15) Uani 1 1 d . . . H33A H 1.0565 0.2696 0.0491 0.190 Uiso 1 1 calc R . . H33B H 0.8921 0.2206 0.0534 0.190 Uiso 1 1 calc R . . H33C H 0.9799 0.2526 0.1069 0.190 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 0.209(3) 0.1018(16) 0.0998(16) -0.0206(14) 0.0363(18) 0.0618(19) O2 0.144(2) 0.0612(10) 0.0923(14) 0.0075(10) 0.0010(13) 0.0311(12) O3 0.0458(8) 0.0761(10) 0.0964(12) -0.0321(9) -0.0174(8) 0.0152(8) O4 0.0603(9) 0.0879(12) 0.0689(10) -0.0372(9) 0.0024(8) 0.0027(9) N1 0.0593(11) 0.0636(11) 0.0593(10) 0.0059(9) -0.0077(9) -0.0166(9) N2 0.0468(9) 0.0562(9) 0.0564(10) -0.0131(8) -0.0079(8) 0.0023(8) C0AA 0.0721(15) 0.0535(12) 0.0665(14) -0.0166(11) -0.0011(12) -0.0032(11) C1 0.0778(17) 0.0869(18) 0.0741(16) 0.0203(14) -0.0131(14) -0.0193(14) C2 0.0688(15) 0.104(2) 0.0748(16) 0.0220(15) -0.0163(13) -0.0120(15) C3 0.0579(13) 0.0896(17) 0.0625(13) -0.0040(13) -0.0039(11) -0.0192(13) C4 0.0468(11) 0.0601(12) 0.0528(11) -0.0183(9) 0.0111(9) -0.0120(9) C5 0.0536(12) 0.0605(13) 0.0593(12) -0.0152(10) 0.0070(10) -0.0102(10) C6 0.0710(14) 0.0512(12) 0.0787(15) -0.0038(11) 0.0161(13) -0.0064(11) C7 0.0671(14) 0.0540(12) 0.0633(13) 0.0013(10) 0.0021(11) 0.0081(11) C8 0.0492(11) 0.0523(11) 0.0570(11) -0.0090(9) 0.0048(9) 0.0001(9) C9 0.0501(11) 0.0525(11) 0.0465(10) -0.0078(9) 0.0028(8) -0.0037(9) C10 0.0460(10) 0.0556(11) 0.0516(11) -0.0057(9) -0.0108(9) 0.0087(10) C11 0.0465(10) 0.0441(9) 0.0412(9) 0.0044(7) -0.0052(8) 0.0012(8) C12 0.0448(10) 0.0570(11) 0.0377(9) -0.0015(8) 0.0041(8) -0.0022(9) C13 0.0510(11) 0.0650(13) 0.0408(10) -0.0086(9) -0.0009(8) 0.0013(10) C14 0.0409(9) 0.0500(10) 0.0475(10) -0.0089(8) 0.0032(8) 0.0067(8) C15 0.0382(9) 0.0602(12) 0.0483(10) -0.0063(9) 0.0059(8) 0.0012(9) C16 0.0356(8) 0.0429(9) 0.0375(8) 0.0030(7) 0.0036(7) -0.0028(7) C17 0.0354(8) 0.0389(8) 0.0366(8) 0.0009(7) 0.0002(7) 0.0018(7) C18 0.0394(9) 0.0405(9) 0.0395(8) 0.0027(7) 0.0034(7) -0.0019(8) C19 0.0436(9) 0.0424(9) 0.0444(9) -0.0020(8) -0.0030(8) 0.0033(8) C20 0.0684(13) 0.0436(10) 0.0626(12) 0.0028(9) 0.0035(11) 0.0075(10) C21 0.104(2) 0.0438(11) 0.0959(19) -0.0053(12) -0.0168(16) 0.0049(13) C22 0.105(2) 0.0580(14) 0.0907(19) 0.0015(13) -0.0284(16) 0.0234(15) C23 0.0365(9) 0.0453(10) 0.0388(9) -0.0006(7) -0.0002(7) -0.0002(7) C24 0.0417(10) 0.0673(13) 0.0585(12) -0.0088(10) 0.0026(9) -0.0086(10) C25 0.0463(11) 0.0770(15) 0.0689(13) -0.0105(11) -0.0026(10) -0.0126(11) C26 0.0598(13) 0.0651(13) 0.0637(13) -0.0118(11) -0.0076(11) -0.0140(11) C27 0.0530(11) 0.0515(11) 0.0467(10) -0.0077(9) -0.0015(9) -0.0030(9) C28 0.0728(14) 0.0815(15) 0.0410(10) -0.0074(10) -0.0048(10) 0.0014(13) C29 0.0444(10) 0.0412(9) 0.0372(8) 0.0006(7) -0.0001(7) -0.0020(8) C30 0.0423(9) 0.0447(9) 0.0471(10) -0.0042(8) 0.0065(8) 0.0034(8) C31 0.0357(9) 0.0427(9) 0.0511(10) -0.0046(8) -0.0010(8) 0.0045(8) C32 0.0568(12) 0.0514(11) 0.0472(10) 0.0028(9) -0.0088(9) 0.0077(9) C33 0.152(4) 0.0628(17) 0.165(4) 0.009(2) -0.024(3) 0.030(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C0AA 1.181(3) . ? O2 C0AA 1.313(3) . ? O2 C33 1.431(4) . ? O3 C10 1.199(3) . ? O4 C13 1.201(3) . ? N1 C1 1.317(3) . ? N1 C9 1.361(3) . ? N2 C13 1.385(3) . ? N2 C10 1.403(3) . ? N2 C8 1.451(3) . ? C0AA C27 1.517(3) . ? C1 C2 1.386(4) . ? C1 H1 0.9300 . ? C2 C3 1.353(4) . ? C2 H2 0.9300 . ? C3 C4 1.407(3) . ? C3 H3 0.9300 . ? C4 C5 1.417(3) . ? C4 C9 1.419(3) . ? C5 C6 1.342(4) . ? C5 H5 0.9300 . ? C6 C7 1.433(3) . ? C6 H6 0.9300 . ? C7 C8 1.351(3) . ? C7 H7 0.9300 . ? C8 C9 1.401(3) . ? C10 C11 1.519(3) . ? C11 C12 1.534(3) . ? C11 C17 1.572(2) . ? C11 H11 0.9800 . ? C12 C13 1.517(3) . ? C12 C14 1.557(3) . ? C12 H12 0.9800 . ? C14 C19 1.516(3) . ? C14 C15 1.543(3) . ? C14 H14 0.9800 . ? C15 C16 1.550(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C23 1.561(2) . ? C16 C17 1.570(2) . ? C16 H16 0.9800 . ? C17 C18 1.503(2) . ? C17 C31 1.529(2) . ? C18 C19 1.329(3) . ? C18 H18 0.9300 . ? C19 C20 1.517(3) . ? C20 C22 1.516(4) . ? C20 C21 1.532(3) . ? C20 H20 0.9800 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.541(3) . ? C23 C32 1.543(3) . ? C23 C29 1.560(3) . ? C24 C25 1.530(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.505(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.559(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.530(3) . ? C27 C29 1.567(3) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.523(3) . ? C29 H29 0.9800 . ? C30 C31 1.531(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 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 C0AA O2 C33 117.7(3) . . ? C1 N1 C9 116.1(2) . . ? C13 N2 C10 113.38(17) . . ? C13 N2 C8 124.22(16) . . ? C10 N2 C8 122.35(16) . . ? O1 C0AA O2 121.0(3) . . ? O1 C0AA C27 125.7(3) . . ? O2 C0AA C27 113.3(2) . . ? N1 C1 C2 125.5(3) . . ? N1 C1 H1 117.2 . . ? C2 C1 H1 117.2 . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 122.91(19) . . ? C3 C4 C9 117.4(2) . . ? C5 C4 C9 119.7(2) . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.7(2) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 119.1(2) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 122.4(2) . . ? C7 C8 N2 119.4(2) . . ? C9 C8 N2 118.23(18) . . ? N1 C9 C8 119.35(18) . . ? N1 C9 C4 122.8(2) . . ? C8 C9 C4 117.82(19) . . ? O3 C10 N2 123.33(19) . . ? O3 C10 C11 128.56(18) . . ? N2 C10 C11 108.10(16) . . ? C10 C11 C12 104.66(16) . . ? C10 C11 C17 112.10(16) . . ? C12 C11 C17 110.94(14) . . ? C10 C11 H11 109.7 . . ? C12 C11 H11 109.7 . . ? C17 C11 H11 109.7 . . ? C13 C12 C11 105.68(16) . . ? C13 C12 C14 111.92(16) . . ? C11 C12 C14 109.16(14) . . ? C13 C12 H12 110.0 . . ? C11 C12 H12 110.0 . . ? C14 C12 H12 110.0 . . ? O4 C13 N2 124.5(2) . . ? O4 C13 C12 127.50(19) . . ? N2 C13 C12 107.95(16) . . ? C19 C14 C15 108.23(15) . . ? C19 C14 C12 108.50(15) . . ? C15 C14 C12 106.45(16) . . ? C19 C14 H14 111.2 . . ? C15 C14 H14 111.2 . . ? C12 C14 H14 111.2 . . ? C14 C15 C16 110.50(15) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C23 114.05(15) . . ? C15 C16 C17 109.23(14) . . ? C23 C16 C17 114.07(13) . . ? C15 C16 H16 106.3 . . ? C23 C16 H16 106.3 . . ? C17 C16 H16 106.3 . . ? C18 C17 C31 115.43(14) . . ? C18 C17 C16 108.74(14) . . ? C31 C17 C16 111.56(14) . . ? C18 C17 C11 105.19(14) . . ? C31 C17 C11 109.80(14) . . ? C16 C17 C11 105.47(14) . . ? C19 C18 C17 116.96(15) . . ? C19 C18 H18 121.5 . . ? C17 C18 H18 121.5 . . ? C18 C19 C14 113.22(16) . . ? C18 C19 C20 124.93(18) . . ? C14 C19 C20 121.63(16) . . ? C22 C20 C19 111.0(2) . . ? C22 C20 C21 110.0(2) . . ? C19 C20 C21 112.88(18) . . ? C22 C20 H20 107.6 . . ? C19 C20 H20 107.6 . . ? C21 C20 H20 107.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C32 108.30(16) . . ? C24 C23 C29 108.50(16) . . ? C32 C23 C29 113.86(15) . . ? C24 C23 C16 107.93(14) . . ? C32 C23 C16 112.41(15) . . ? C29 C23 C16 105.63(14) . . ? C25 C24 C23 113.34(17) . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C26 C25 C24 111.01(19) . . ? C26 C25 H25A 109.4 . . ? C24 C25 H25A 109.4 . . ? C26 C25 H25B 109.4 . . ? C24 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C27 113.86(18) . . ? C25 C26 H26A 108.8 . . ? C27 C26 H26A 108.8 . . ? C25 C26 H26B 108.8 . . ? C27 C26 H26B 108.8 . . ? H26A C26 H26B 107.7 . . ? C0AA C27 C28 107.26(18) . . ? C0AA C27 C26 106.70(18) . . ? C28 C27 C26 110.78(19) . . ? C0AA C27 C29 108.17(16) . . ? C28 C27 C29 114.67(17) . . ? C26 C27 C29 108.92(16) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 C23 110.68(15) . . ? C30 C29 C27 113.22(15) . . ? C23 C29 C27 116.45(15) . . ? C30 C29 H29 105.1 . . ? C23 C29 H29 105.1 . . ? C27 C29 H29 105.1 . . ? C29 C30 C31 110.51(15) . . ? C29 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C17 C31 C30 113.76(15) . . ? C17 C31 H31A 108.8 . . ? C30 C31 H31A 108.8 . . ? C17 C31 H31B 108.8 . . ? C30 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C23 C32 H32A 109.5 . . ? C23 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C23 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O2 C33 H33A 109.5 . . ? O2 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O2 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 C33 O2 C0AA O1 -4.5(5) . . . . ? C33 O2 C0AA C27 175.0(3) . . . . ? C9 N1 C1 C2 -0.3(4) . . . . ? N1 C1 C2 C3 0.5(5) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 177.8(2) . . . . ? C2 C3 C4 C9 -1.9(3) . . . . ? C3 C4 C5 C6 179.4(2) . . . . ? C9 C4 C5 C6 -0.9(3) . . . . ? C4 C5 C6 C7 -0.9(3) . . . . ? C5 C6 C7 C8 1.5(3) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C6 C7 C8 N2 -179.96(19) . . . . ? C13 N2 C8 C7 -75.4(3) . . . . ? C10 N2 C8 C7 107.2(2) . . . . ? C13 N2 C8 C9 105.0(2) . . . . ? C10 N2 C8 C9 -72.5(3) . . . . ? C1 N1 C9 C8 179.4(2) . . . . ? C1 N1 C9 C4 -0.9(3) . . . . ? C7 C8 C9 N1 178.3(2) . . . . ? N2 C8 C9 N1 -2.1(3) . . . . ? C7 C8 C9 C4 -1.4(3) . . . . ? N2 C8 C9 C4 178.22(17) . . . . ? C3 C4 C9 N1 2.0(3) . . . . ? C5 C4 C9 N1 -177.64(19) . . . . ? C3 C4 C9 C8 -178.3(2) . . . . ? C5 C4 C9 C8 2.0(3) . . . . ? C13 N2 C10 O3 -177.6(2) . . . . ? C8 N2 C10 O3 0.1(3) . . . . ? C13 N2 C10 C11 2.7(2) . . . . ? C8 N2 C10 C11 -179.60(18) . . . . ? O3 C10 C11 C12 -179.3(2) . . . . ? N2 C10 C11 C12 0.4(2) . . . . ? O3 C10 C11 C17 -58.9(3) . . . . ? N2 C10 C11 C17 120.76(17) . . . . ? C10 C11 C12 C13 -3.02(19) . . . . ? C17 C11 C12 C13 -124.12(16) . . . . ? C10 C11 C12 C14 117.51(17) . . . . ? C17 C11 C12 C14 -3.6(2) . . . . ? C10 N2 C13 O4 177.0(2) . . . . ? C8 N2 C13 O4 -0.7(4) . . . . ? C10 N2 C13 C12 -4.7(2) . . . . ? C8 N2 C13 C12 177.64(19) . . . . ? C11 C12 C13 O4 -177.1(2) . . . . ? C14 C12 C13 O4 64.2(3) . . . . ? C11 C12 C13 N2 4.7(2) . . . . ? C14 C12 C13 N2 -114.03(19) . . . . ? C13 C12 C14 C19 64.07(19) . . . . ? C11 C12 C14 C19 -52.6(2) . . . . ? C13 C12 C14 C15 -179.66(15) . . . . ? C11 C12 C14 C15 63.72(19) . . . . ? C19 C14 C15 C16 56.7(2) . . . . ? C12 C14 C15 C16 -59.77(19) . . . . ? C14 C15 C16 C23 -132.47(16) . . . . ? C14 C15 C16 C17 -3.5(2) . . . . ? C15 C16 C17 C18 -50.08(18) . . . . ? C23 C16 C17 C18 78.87(17) . . . . ? C15 C16 C17 C31 -178.52(15) . . . . ? C23 C16 C17 C31 -49.57(19) . . . . ? C15 C16 C17 C11 62.31(17) . . . . ? C23 C16 C17 C11 -168.74(14) . . . . ? C10 C11 C17 C18 -60.37(19) . . . . ? C12 C11 C17 C18 56.23(18) . . . . ? C10 C11 C17 C31 64.42(19) . . . . ? C12 C11 C17 C31 -178.97(15) . . . . ? C10 C11 C17 C16 -175.25(15) . . . . ? C12 C11 C17 C16 -58.64(18) . . . . ? C31 C17 C18 C19 -178.24(16) . . . . ? C16 C17 C18 C19 55.5(2) . . . . ? C11 C17 C18 C19 -57.1(2) . . . . ? C17 C18 C19 C14 -0.1(2) . . . . ? C17 C18 C19 C20 -174.77(17) . . . . ? C15 C14 C19 C18 -57.3(2) . . . . ? C12 C14 C19 C18 57.8(2) . . . . ? C15 C14 C19 C20 117.56(19) . . . . ? C12 C14 C19 C20 -127.32(19) . . . . ? C18 C19 C20 C22 105.5(2) . . . . ? C14 C19 C20 C22 -68.7(3) . . . . ? C18 C19 C20 C21 -130.5(2) . . . . ? C14 C19 C20 C21 55.3(3) . . . . ? C15 C16 C23 C24 -61.1(2) . . . . ? C17 C16 C23 C24 172.46(15) . . . . ? C15 C16 C23 C32 58.3(2) . . . . ? C17 C16 C23 C32 -68.18(19) . . . . ? C15 C16 C23 C29 -176.98(14) . . . . ? C17 C16 C23 C29 56.55(18) . . . . ? C32 C23 C24 C25 70.5(2) . . . . ? C29 C23 C24 C25 -53.6(2) . . . . ? C16 C23 C24 C25 -167.60(18) . . . . ? C23 C24 C25 C26 58.3(3) . . . . ? C24 C25 C26 C27 -56.5(3) . . . . ? O1 C0AA C27 C28 -5.6(4) . . . . ? O2 C0AA C27 C28 174.8(2) . . . . ? O1 C0AA C27 C26 113.1(3) . . . . ? O2 C0AA C27 C26 -66.4(3) . . . . ? O1 C0AA C27 C29 -129.8(3) . . . . ? O2 C0AA C27 C29 50.6(3) . . . . ? C25 C26 C27 C0AA 167.37(19) . . . . ? C25 C26 C27 C28 -76.2(2) . . . . ? C25 C26 C27 C29 50.8(2) . . . . ? C24 C23 C29 C30 -178.43(16) . . . . ? C32 C23 C29 C30 60.9(2) . . . . ? C16 C23 C29 C30 -62.92(18) . . . . ? C24 C23 C29 C27 50.4(2) . . . . ? C32 C23 C29 C27 -70.3(2) . . . . ? C16 C23 C29 C27 165.90(15) . . . . ? C0AA C27 C29 C30 65.6(2) . . . . ? C28 C27 C29 C30 -54.0(2) . . . . ? C26 C27 C29 C30 -178.76(17) . . . . ? C0AA C27 C29 C23 -164.38(17) . . . . ? C28 C27 C29 C23 76.0(2) . . . . ? C26 C27 C29 C23 -48.8(2) . . . . ? C23 C29 C30 C31 62.82(19) . . . . ? C27 C29 C30 C31 -164.34(16) . . . . ? C18 C17 C31 C30 -78.4(2) . . . . ? C16 C17 C31 C30 46.4(2) . . . . ? C11 C17 C31 C30 162.92(15) . . . . ? C29 C30 C31 C17 -53.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.194 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.030 _database_code_depnum_ccdc_archive 'CCDC 948185'