# 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_shelx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 N2 O2' _chemical_formula_weight 444.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.329(4) _cell_length_b 10.683(4) _cell_length_c 21.433(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.916(6) _cell_angle_gamma 90.00 _cell_volume 2361.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7908 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9844 _exptl_absorpt_correction_T_max 0.9906 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.22 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28992 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.88 _reflns_number_total 5627 _reflns_number_gt 4947 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0614P)^2^+0.1877P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5627 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1311 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.35034(9) 0.56393(9) 1.09917(4) 0.0323(2) Uani 1 1 d . . . O2 O 0.20998(8) 0.70062(9) 1.05137(4) 0.0296(2) Uani 1 1 d . . . N1 N 0.52482(11) 0.33580(11) 1.03652(6) 0.0321(3) Uani 1 1 d . . . N2 N 0.14015(12) 0.24626(12) 1.09289(6) 0.0370(3) Uani 1 1 d . . . C1 C 0.41601(12) 0.35178(12) 1.02624(6) 0.0250(3) Uani 1 1 d . . . C2 C 0.20267(12) 0.29500(12) 1.05736(6) 0.0258(3) Uani 1 1 d . . . C3 C 0.27473(11) 0.36478(12) 1.01033(6) 0.0226(3) Uani 1 1 d . . . C4 C 0.23621(11) 0.31720(12) 0.94149(6) 0.0216(3) Uani 1 1 d . . . C5 C 0.33881(11) 0.35788(12) 0.89538(6) 0.0232(3) Uani 1 1 d . . . H5A H 0.3774 0.4397 0.9075 0.028 Uiso 1 1 calc R . . H5B H 0.4087 0.2948 0.8934 0.028 Uiso 1 1 calc R . . C6 C 0.26016(11) 0.36708(12) 0.83261(6) 0.0224(3) Uani 1 1 d . . . H6 H 0.2356 0.2805 0.8189 0.027 Uiso 1 1 calc R . . C7 C 0.13525(11) 0.43669(12) 0.85012(6) 0.0217(3) Uani 1 1 d . . . H7 H 0.1540 0.5284 0.8481 0.026 Uiso 1 1 calc R . . C8 C 0.11940(11) 0.40367(12) 0.92055(6) 0.0219(3) Uani 1 1 d . . . H8 H 0.0347 0.3612 0.9266 0.026 Uiso 1 1 calc R . . C9 C 0.13643(12) 0.51543(12) 0.96234(6) 0.0229(3) Uani 1 1 d . . . H9 H 0.0892 0.5910 0.9558 0.027 Uiso 1 1 calc R . . C10 C 0.22365(12) 0.49947(12) 1.00948(6) 0.0226(3) Uani 1 1 d . . . C11 C 0.26895(12) 0.58928(12) 1.05848(6) 0.0244(3) Uani 1 1 d . . . C12 C 0.26034(15) 0.79731(14) 1.09372(7) 0.0379(4) Uani 1 1 d . . . H12A H 0.2474 0.7721 1.1369 0.057 Uiso 1 1 calc R . . H12B H 0.2145 0.8761 1.0847 0.057 Uiso 1 1 calc R . . H12C H 0.3531 0.8089 1.0881 0.057 Uiso 1 1 calc R . . C13 C 0.01343(12) 0.41300(12) 0.80865(6) 0.0240(3) Uani 1 1 d . . . C14 C -0.07690(13) 0.50863(14) 0.80007(7) 0.0322(3) Uani 1 1 d . . . H14 H -0.0589 0.5885 0.8179 0.039 Uiso 1 1 calc R . . C15 C -0.19334(14) 0.48949(15) 0.76581(8) 0.0407(4) Uani 1 1 d . . . H15 H -0.2540 0.5560 0.7607 0.049 Uiso 1 1 calc R . . C16 C -0.22107(14) 0.37466(17) 0.73930(7) 0.0404(4) Uani 1 1 d . . . H16 H -0.2999 0.3618 0.7153 0.048 Uiso 1 1 calc R . . C17 C -0.13296(15) 0.27839(17) 0.74797(9) 0.0481(4) Uani 1 1 d . . . H17 H -0.1519 0.1984 0.7304 0.058 Uiso 1 1 calc R . . C18 C -0.01643(14) 0.29748(15) 0.78227(8) 0.0421(4) Uani 1 1 d . . . H18 H 0.0434 0.2303 0.7876 0.050 Uiso 1 1 calc R . . C19 C 0.33076(12) 0.42933(12) 0.78058(6) 0.0247(3) Uani 1 1 d . . . C20 C 0.40091(13) 0.53988(13) 0.79093(7) 0.0314(3) Uani 1 1 d . . . H20 H 0.4029 0.5783 0.8309 0.038 Uiso 1 1 calc R . . C21 C 0.46775(13) 0.59414(15) 0.74320(7) 0.0374(4) Uani 1 1 d . . . H21 H 0.5142 0.6699 0.7506 0.045 Uiso 1 1 calc R . . C22 C 0.46701(14) 0.53846(16) 0.68491(7) 0.0406(4) Uani 1 1 d . . . H22 H 0.5155 0.5739 0.6528 0.049 Uiso 1 1 calc R . . C23 C 0.39565(16) 0.43148(16) 0.67368(7) 0.0439(4) Uani 1 1 d . . . H23 H 0.3933 0.3940 0.6334 0.053 Uiso 1 1 calc R . . C24 C 0.32673(14) 0.37786(14) 0.72114(7) 0.0340(3) Uani 1 1 d . . . H24 H 0.2762 0.3049 0.7126 0.041 Uiso 1 1 calc R . . C25 C 0.21365(12) 0.17625(12) 0.93852(6) 0.0251(3) Uani 1 1 d . . . C26 C 0.09575(15) 0.12329(15) 0.91977(9) 0.0466(4) Uani 1 1 d . . . H26 H 0.0239 0.1762 0.9096 0.056 Uiso 1 1 calc R . . C27 C 0.08034(19) -0.00556(16) 0.91554(10) 0.0590(5) Uani 1 1 d . . . H27 H -0.0013 -0.0396 0.9020 0.071 Uiso 1 1 calc R . . C28 C 0.18213(18) -0.08412(15) 0.93083(8) 0.0471(4) Uani 1 1 d . . . H28 H 0.1711 -0.1723 0.9283 0.057 Uiso 1 1 calc R . . C29 C 0.29977(17) -0.03429(14) 0.94982(7) 0.0421(4) Uani 1 1 d . . . H29 H 0.3706 -0.0882 0.9605 0.050 Uiso 1 1 calc R . . C30 C 0.31616(14) 0.09475(13) 0.95352(7) 0.0326(3) Uani 1 1 d . . . H30 H 0.3985 0.1280 0.9665 0.039 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 0.0261(5) 0.0423(6) 0.0280(5) -0.0023(4) -0.0032(4) -0.0009(4) O2 0.0264(5) 0.0285(5) 0.0335(5) -0.0082(4) -0.0016(4) -0.0008(4) N1 0.0246(6) 0.0354(7) 0.0360(7) 0.0019(5) -0.0017(5) -0.0002(5) N2 0.0395(7) 0.0393(7) 0.0326(7) 0.0007(5) 0.0050(5) -0.0117(6) C1 0.0240(7) 0.0253(7) 0.0256(6) 0.0018(5) -0.0006(5) -0.0007(5) C2 0.0238(7) 0.0272(7) 0.0263(7) 0.0008(5) -0.0014(5) -0.0031(5) C3 0.0173(6) 0.0257(7) 0.0247(6) 0.0021(5) -0.0003(5) -0.0021(5) C4 0.0177(6) 0.0236(6) 0.0233(6) 0.0013(5) 0.0000(5) -0.0022(5) C5 0.0175(6) 0.0254(7) 0.0267(6) 0.0029(5) 0.0002(5) -0.0001(5) C6 0.0184(6) 0.0222(6) 0.0265(6) 0.0012(5) 0.0002(5) -0.0008(5) C7 0.0193(6) 0.0203(6) 0.0254(6) 0.0002(5) -0.0013(5) -0.0004(5) C8 0.0157(6) 0.0238(6) 0.0261(6) -0.0006(5) 0.0000(5) -0.0017(5) C9 0.0166(6) 0.0241(6) 0.0281(7) -0.0004(5) 0.0028(5) -0.0003(5) C10 0.0175(6) 0.0248(7) 0.0258(6) 0.0004(5) 0.0025(5) -0.0024(5) C11 0.0184(6) 0.0291(7) 0.0259(6) -0.0013(5) 0.0040(5) -0.0032(5) C12 0.0361(8) 0.0367(8) 0.0407(8) -0.0169(7) 0.0003(6) -0.0044(6) C13 0.0188(6) 0.0296(7) 0.0236(6) -0.0003(5) 0.0000(5) -0.0008(5) C14 0.0241(7) 0.0321(8) 0.0399(8) -0.0005(6) -0.0037(6) 0.0019(6) C15 0.0251(7) 0.0436(9) 0.0524(10) 0.0060(7) -0.0087(7) 0.0045(6) C16 0.0237(7) 0.0626(11) 0.0340(8) -0.0043(7) -0.0080(6) -0.0025(7) C17 0.0303(8) 0.0550(11) 0.0579(11) -0.0256(9) -0.0084(7) -0.0017(7) C18 0.0271(8) 0.0390(9) 0.0588(10) -0.0185(7) -0.0100(7) 0.0053(6) C19 0.0186(6) 0.0288(7) 0.0265(7) 0.0057(5) -0.0012(5) 0.0029(5) C20 0.0266(7) 0.0331(8) 0.0345(7) 0.0052(6) 0.0012(6) -0.0028(6) C21 0.0232(7) 0.0409(9) 0.0479(9) 0.0172(7) 0.0011(6) -0.0043(6) C22 0.0296(8) 0.0549(10) 0.0379(8) 0.0234(7) 0.0064(6) 0.0069(7) C23 0.0509(10) 0.0550(11) 0.0261(7) 0.0086(7) 0.0044(7) 0.0018(8) C24 0.0360(8) 0.0377(8) 0.0280(7) 0.0041(6) -0.0010(6) -0.0024(6) C25 0.0265(7) 0.0244(7) 0.0247(6) 0.0009(5) 0.0040(5) -0.0011(5) C26 0.0325(8) 0.0272(8) 0.0795(13) 0.0007(8) -0.0038(8) -0.0056(6) C27 0.0488(11) 0.0306(9) 0.0973(16) -0.0013(9) -0.0009(10) -0.0128(8) C28 0.0677(12) 0.0217(8) 0.0525(10) 0.0020(7) 0.0085(9) -0.0061(7) C29 0.0591(11) 0.0276(8) 0.0397(9) 0.0032(6) 0.0037(7) 0.0099(7) C30 0.0355(8) 0.0283(7) 0.0337(7) 0.0004(6) -0.0006(6) 0.0038(6) _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 C11 1.2108(15) . ? O2 C11 1.3415(16) . ? O2 C12 1.4538(16) . ? N1 C1 1.1471(17) . ? N2 C2 1.1480(17) . ? C1 C3 1.4880(18) . ? C2 C3 1.4839(18) . ? C3 C10 1.5323(18) . ? C3 C4 1.5918(18) . ? C4 C25 1.5246(18) . ? C4 C5 1.5476(17) . ? C4 C8 1.5669(17) . ? C5 C6 1.5391(17) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C19 1.5165(18) . ? C6 C7 1.5516(17) . ? C6 H6 1.0000 . ? C7 C13 1.5242(17) . ? C7 C8 1.5670(18) . ? C7 H7 1.0000 . ? C8 C9 1.4975(18) . ? C8 H8 1.0000 . ? C9 C10 1.3300(17) . ? C9 H9 0.9500 . ? C10 C11 1.4806(18) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.386(2) . ? C13 C14 1.3894(19) . ? C14 C15 1.392(2) . ? C14 H14 0.9500 . ? C15 C16 1.376(2) . ? C15 H15 0.9500 . ? C16 C17 1.380(2) . ? C16 H16 0.9500 . ? C17 C18 1.393(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.3864(19) . ? C19 C20 1.3974(19) . ? C20 C21 1.390(2) . ? C20 H20 0.9500 . ? C21 C22 1.383(2) . ? C21 H21 0.9500 . ? C22 C23 1.375(2) . ? C22 H22 0.9500 . ? C23 C24 1.394(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.384(2) . ? C25 C30 1.3957(19) . ? C26 C27 1.388(2) . ? C26 H26 0.9500 . ? C27 C28 1.372(3) . ? C27 H27 0.9500 . ? C28 C29 1.369(2) . ? C28 H28 0.9500 . ? C29 C30 1.391(2) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O2 C12 114.39(11) . . ? N1 C1 C3 176.17(14) . . ? N2 C2 C3 175.47(14) . . ? C2 C3 C1 108.51(10) . . ? C2 C3 C10 107.19(10) . . ? C1 C3 C10 115.05(10) . . ? C2 C3 C4 111.03(10) . . ? C1 C3 C4 112.24(10) . . ? C10 C3 C4 102.66(9) . . ? C25 C4 C5 111.03(10) . . ? C25 C4 C8 117.16(10) . . ? C5 C4 C8 101.18(10) . . ? C25 C4 C3 112.62(10) . . ? C5 C4 C3 110.81(10) . . ? C8 C4 C3 103.28(10) . . ? C6 C5 C4 103.19(10) . . ? C6 C5 H5A 111.1 . . ? C4 C5 H5A 111.1 . . ? C6 C5 H5B 111.1 . . ? C4 C5 H5B 111.1 . . ? H5A C5 H5B 109.1 . . ? C19 C6 C5 114.75(10) . . ? C19 C6 C7 113.86(10) . . ? C5 C6 C7 103.15(10) . . ? C19 C6 H6 108.3 . . ? C5 C6 H6 108.3 . . ? C7 C6 H6 108.3 . . ? C13 C7 C6 116.83(11) . . ? C13 C7 C8 113.62(10) . . ? C6 C7 C8 104.72(9) . . ? C13 C7 H7 107.0 . . ? C6 C7 H7 107.0 . . ? C8 C7 H7 107.0 . . ? C9 C8 C4 103.50(10) . . ? C9 C8 C7 112.45(11) . . ? C4 C8 C7 106.98(9) . . ? C9 C8 H8 111.2 . . ? C4 C8 H8 111.2 . . ? C7 C8 H8 111.2 . . ? C10 C9 C8 113.99(11) . . ? C10 C9 H9 123.0 . . ? C8 C9 H9 123.0 . . ? C9 C10 C11 129.29(12) . . ? C9 C10 C3 110.42(11) . . ? C11 C10 C3 120.25(11) . . ? O1 C11 O2 125.08(12) . . ? O1 C11 C10 123.28(12) . . ? O2 C11 C10 111.63(11) . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 117.82(12) . . ? C18 C13 C7 123.08(12) . . ? C14 C13 C7 118.95(12) . . ? C13 C14 C15 121.21(14) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 120.33(14) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.13(14) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C18 120.56(15) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 120.94(14) . . ? C13 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C24 C19 C20 118.17(13) . . ? C24 C19 C6 120.58(12) . . ? C20 C19 C6 121.25(12) . . ? C21 C20 C19 120.58(14) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 120.36(15) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C23 C22 C21 119.60(14) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 120.21(15) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C19 C24 C23 121.00(14) . . ? C19 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C26 C25 C30 117.26(13) . . ? C26 C25 C4 123.12(12) . . ? C30 C25 C4 119.60(12) . . ? C25 C26 C27 121.38(16) . . ? C25 C26 H26 119.3 . . ? C27 C26 H26 119.3 . . ? C28 C27 C26 120.47(17) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C29 C28 C27 119.40(15) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? C28 C29 C30 120.39(15) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C29 C30 C25 121.09(14) . . ? C29 C30 H30 119.5 . . ? C25 C30 H30 119.5 . . ? 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 N2 C2 C3 C1 154.1(17) . . . . ? N2 C2 C3 C10 29.3(18) . . . . ? N2 C2 C3 C4 -82.0(18) . . . . ? N1 C1 C3 C2 89(2) . . . . ? N1 C1 C3 C10 -151(2) . . . . ? N1 C1 C3 C4 -34(2) . . . . ? C2 C3 C4 C25 -37.16(14) . . . . ? C1 C3 C4 C25 84.48(13) . . . . ? C10 C3 C4 C25 -151.41(10) . . . . ? C2 C3 C4 C5 -162.20(10) . . . . ? C1 C3 C4 C5 -40.56(14) . . . . ? C10 C3 C4 C5 83.55(11) . . . . ? C2 C3 C4 C8 90.17(12) . . . . ? C1 C3 C4 C8 -148.18(10) . . . . ? C10 C3 C4 C8 -24.08(11) . . . . ? C25 C4 C5 C6 81.90(12) . . . . ? C8 C4 C5 C6 -43.16(11) . . . . ? C3 C4 C5 C6 -152.17(10) . . . . ? C4 C5 C6 C19 168.88(10) . . . . ? C4 C5 C6 C7 44.47(12) . . . . ? C19 C6 C7 C13 81.20(14) . . . . ? C5 C6 C7 C13 -153.81(11) . . . . ? C19 C6 C7 C8 -152.13(10) . . . . ? C5 C6 C7 C8 -27.14(12) . . . . ? C25 C4 C8 C9 146.20(11) . . . . ? C5 C4 C8 C9 -92.97(11) . . . . ? C3 C4 C8 C9 21.78(12) . . . . ? C25 C4 C8 C7 -94.86(12) . . . . ? C5 C4 C8 C7 25.97(12) . . . . ? C3 C4 C8 C7 140.73(10) . . . . ? C13 C7 C8 C9 -117.91(12) . . . . ? C6 C7 C8 C9 113.46(11) . . . . ? C13 C7 C8 C4 129.12(11) . . . . ? C6 C7 C8 C4 0.50(12) . . . . ? C4 C8 C9 C10 -11.68(14) . . . . ? C7 C8 C9 C10 -126.78(12) . . . . ? C8 C9 C10 C11 177.85(12) . . . . ? C8 C9 C10 C3 -4.57(15) . . . . ? C2 C3 C10 C9 -98.57(12) . . . . ? C1 C3 C10 C9 140.68(12) . . . . ? C4 C3 C10 C9 18.45(13) . . . . ? C2 C3 C10 C11 79.26(14) . . . . ? C1 C3 C10 C11 -41.49(16) . . . . ? C4 C3 C10 C11 -163.72(10) . . . . ? C12 O2 C11 O1 5.75(18) . . . . ? C12 O2 C11 C10 -173.50(11) . . . . ? C9 C10 C11 O1 -179.49(13) . . . . ? C3 C10 C11 O1 3.13(19) . . . . ? C9 C10 C11 O2 -0.23(19) . . . . ? C3 C10 C11 O2 -177.60(10) . . . . ? C6 C7 C13 C18 36.47(18) . . . . ? C8 C7 C13 C18 -85.66(16) . . . . ? C6 C7 C13 C14 -148.10(12) . . . . ? C8 C7 C13 C14 89.77(15) . . . . ? C18 C13 C14 C15 -0.4(2) . . . . ? C7 C13 C14 C15 -176.04(13) . . . . ? C13 C14 C15 C16 -0.3(2) . . . . ? C14 C15 C16 C17 1.0(2) . . . . ? C15 C16 C17 C18 -1.0(3) . . . . ? C14 C13 C18 C17 0.4(2) . . . . ? C7 C13 C18 C17 175.86(15) . . . . ? C16 C17 C18 C13 0.3(3) . . . . ? C5 C6 C19 C24 135.22(13) . . . . ? C7 C6 C19 C24 -106.23(14) . . . . ? C5 C6 C19 C20 -45.07(17) . . . . ? C7 C6 C19 C20 73.47(15) . . . . ? C24 C19 C20 C21 -1.9(2) . . . . ? C6 C19 C20 C21 178.40(12) . . . . ? C19 C20 C21 C22 -0.8(2) . . . . ? C20 C21 C22 C23 2.5(2) . . . . ? C21 C22 C23 C24 -1.4(2) . . . . ? C20 C19 C24 C23 3.0(2) . . . . ? C6 C19 C24 C23 -177.32(13) . . . . ? C22 C23 C24 C19 -1.3(2) . . . . ? C5 C4 C25 C26 -116.95(15) . . . . ? C8 C4 C25 C26 -1.44(19) . . . . ? C3 C4 C25 C26 118.13(15) . . . . ? C5 C4 C25 C30 61.19(15) . . . . ? C8 C4 C25 C30 176.70(11) . . . . ? C3 C4 C25 C30 -63.73(15) . . . . ? C30 C25 C26 C27 -0.5(2) . . . . ? C4 C25 C26 C27 177.65(16) . . . . ? C25 C26 C27 C28 0.9(3) . . . . ? C26 C27 C28 C29 -0.6(3) . . . . ? C27 C28 C29 C30 -0.1(3) . . . . ? C28 C29 C30 C25 0.5(2) . . . . ? C26 C25 C30 C29 -0.1(2) . . . . ? C4 C25 C30 C29 -178.40(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.178 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 963723'