# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Shigeo Kohmoto' _publ_contact_author_email KOHMOTO@FACULTY.CHIBA-U.JP _publ_section_title ; Reversal of Regioselectivity (Straight vs. Cross Ring Closure) in the Intramolecular [2+2] Photocycloaddition of Phenanthrene Derivatives ; loop_ _publ_author_name 'Shigeo Kohmoto' 'Isao Azumaya' 'Shugo Hisamatsu' 'Keiki Kishikawa' 'Hyuma Masu' ; H.Mitsuhashi ; 'Masahiro Takahashi' #===END data_2a(a0601122mas) _database_code_depnum_ccdc_archive 'CCDC 606845' #TrackingRef 'CIF_kohmoto_compound_1a-3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H25 N O2' _chemical_formula_weight 467.54 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.05670(10) _cell_length_b 9.25440(10) _cell_length_c 19.7847(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.23 _cell_angle_gamma 90.00 _cell_volume 2352.65(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 8803 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 26.25 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26400 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4812 _reflns_number_gt 3985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+1.0098P] 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 4812 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 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 N1 N 1.03138(8) 0.54095(12) 0.16096(5) 0.0243(2) Uani 1 1 d . . . O2 O 1.12070(7) 0.72489(10) 0.22335(5) 0.0321(2) Uani 1 1 d . . . O1 O 0.92493(7) 0.34897(12) 0.12373(5) 0.0352(2) Uani 1 1 d . . . C4 C 0.79844(9) 0.40202(14) 0.30645(6) 0.0231(3) Uani 1 1 d . . . C20 C 0.82561(10) 0.74436(14) 0.37269(6) 0.0251(3) Uani 1 1 d . . . H20 H 0.7707 0.7603 0.3350 0.030 Uiso 1 1 calc R . . C30 C 1.10710(9) 0.52741(14) 0.34162(6) 0.0224(3) Uani 1 1 d . . . C18 C 0.92032(9) 0.62235(14) 0.29021(6) 0.0216(3) Uani 1 1 d . . . H18 H 0.9043 0.7055 0.2578 0.026 Uiso 1 1 calc R . . C3 C 0.85661(9) 0.48455(14) 0.25972(6) 0.0220(3) Uani 1 1 d . . . H3 H 0.8096 0.5088 0.2156 0.026 Uiso 1 1 calc R . . C25 C 1.09366(9) 0.57293(14) 0.40704(6) 0.0233(3) Uani 1 1 d . . . C10 C 0.93212(10) 0.20356(14) 0.32217(6) 0.0242(3) Uani 1 1 d . . . C9 C 0.83744(9) 0.27408(14) 0.33917(6) 0.0240(3) Uani 1 1 d . . . C19 C 0.91449(9) 0.67035(13) 0.36208(6) 0.0215(3) Uani 1 1 d . . . C24 C 0.99650(9) 0.64754(14) 0.41729(6) 0.0232(3) Uani 1 1 d . . . C15 C 0.98576(9) 0.26503(14) 0.27372(6) 0.0242(3) Uani 1 1 d . . . C27 C 1.26780(11) 0.48497(17) 0.45265(7) 0.0341(3) Uani 1 1 d . . . H27 H 1.3222 0.4707 0.4908 0.041 Uiso 1 1 calc R . . C21 C 0.81578(10) 0.79502(15) 0.43705(7) 0.0294(3) Uani 1 1 d . . . H21 H 0.7542 0.8435 0.4436 0.035 Uiso 1 1 calc R . . C29 C 1.20047(10) 0.46248(15) 0.33304(7) 0.0287(3) Uani 1 1 d . . . H29 H 1.2088 0.4315 0.2886 0.034 Uiso 1 1 calc R . . C2 C 0.95973(9) 0.41394(14) 0.24560(6) 0.0220(3) Uani 1 1 d . . . C8 C 0.77964(11) 0.20856(16) 0.38443(7) 0.0304(3) Uani 1 1 d . . . H8 H 0.8054 0.1229 0.4080 0.036 Uiso 1 1 calc R . . C28 C 1.28098(11) 0.44226(16) 0.38778(7) 0.0333(3) Uani 1 1 d . . . H28 H 1.3445 0.3996 0.3809 0.040 Uiso 1 1 calc R . . C7 C 0.68629(11) 0.26604(17) 0.39542(7) 0.0348(3) Uani 1 1 d . . . H7 H 0.6495 0.2208 0.4270 0.042 Uiso 1 1 calc R . . C26 C 1.17558(10) 0.54845(16) 0.46201(7) 0.0303(3) Uani 1 1 d . . . H26 H 1.1675 0.5763 0.5070 0.036 Uiso 1 1 calc R . . C11 C 0.96525(11) 0.06776(16) 0.34918(7) 0.0324(3) Uani 1 1 d . . . H11 H 0.9315 0.0256 0.3831 0.039 Uiso 1 1 calc R . . C5 C 0.70234(10) 0.45605(16) 0.31643(7) 0.0289(3) Uani 1 1 d . . . H5 H 0.6749 0.5404 0.2924 0.035 Uiso 1 1 calc R . . C16 C 1.06680(9) 0.61824(14) 0.22077(6) 0.0232(3) Uani 1 1 d . . . C23 C 0.98546(10) 0.70237(16) 0.48178(7) 0.0309(3) Uani 1 1 d . . . H23 H 1.0406 0.6896 0.5197 0.037 Uiso 1 1 calc R . . C14 C 1.06616(11) 0.18791(16) 0.25239(7) 0.0324(3) Uani 1 1 d . . . H14 H 1.1014 0.2292 0.2190 0.039 Uiso 1 1 calc R . . C6 C 0.64626(10) 0.38885(17) 0.36077(7) 0.0336(3) Uani 1 1 d . . . H6 H 0.5811 0.4268 0.3672 0.040 Uiso 1 1 calc R . . C31 C 1.05262(10) 0.58565(17) 0.09362(6) 0.0301(3) Uani 1 1 d . . . H31A H 1.0440 0.6917 0.0892 0.036 Uiso 1 1 calc R . . H31B H 1.0007 0.5402 0.0573 0.036 Uiso 1 1 calc R . . C17 C 1.02368(9) 0.54782(13) 0.27946(6) 0.0210(3) Uani 1 1 d . . . C22 C 0.89644(11) 0.77442(17) 0.49155(7) 0.0334(3) Uani 1 1 d . . . H22 H 0.8908 0.8098 0.5358 0.040 Uiso 1 1 calc R . . C1 C 0.96767(9) 0.42528(15) 0.16979(6) 0.0245(3) Uani 1 1 d . . . C12 C 1.04562(11) -0.00627(16) 0.32779(8) 0.0370(3) Uani 1 1 d . . . H12 H 1.0663 -0.0981 0.3469 0.044 Uiso 1 1 calc R . . C32 C 1.16144(11) 0.54526(18) 0.08215(7) 0.0377(4) Uani 1 1 d . . . H32A H 1.1705 0.5803 0.0363 0.045 Uiso 1 1 calc R . . H32B H 1.2133 0.5955 0.1168 0.045 Uiso 1 1 calc R . . C13 C 1.09579(11) 0.05310(16) 0.27870(8) 0.0378(3) Uani 1 1 d . . . H13 H 1.1502 0.0018 0.2631 0.045 Uiso 1 1 calc R . . C33 C 1.18350(13) 0.3847(2) 0.08655(9) 0.0497(4) Uani 1 1 d . . . H33A H 1.1892 0.3527 0.1343 0.075 Uiso 1 1 calc R . . H33B H 1.2490 0.3648 0.0705 0.075 Uiso 1 1 calc R . . H33C H 1.1266 0.3325 0.0577 0.075 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 N1 0.0266(5) 0.0276(6) 0.0201(5) 0.0003(4) 0.0081(4) -0.0017(5) O2 0.0388(5) 0.0257(5) 0.0349(5) -0.0012(4) 0.0152(4) -0.0095(4) O1 0.0337(5) 0.0449(6) 0.0276(5) -0.0111(5) 0.0072(4) -0.0099(5) C4 0.0217(6) 0.0259(7) 0.0216(6) -0.0048(5) 0.0041(5) -0.0058(5) C20 0.0261(6) 0.0225(7) 0.0272(6) 0.0003(5) 0.0058(5) 0.0009(5) C30 0.0231(6) 0.0187(6) 0.0257(6) 0.0002(5) 0.0052(5) -0.0036(5) C18 0.0226(6) 0.0212(6) 0.0213(6) 0.0021(5) 0.0051(5) 0.0003(5) C3 0.0218(6) 0.0238(7) 0.0206(6) 0.0001(5) 0.0040(5) 0.0003(5) C25 0.0243(6) 0.0212(7) 0.0248(6) 0.0003(5) 0.0051(5) -0.0030(5) C10 0.0244(6) 0.0221(7) 0.0251(6) -0.0022(5) 0.0014(5) -0.0061(5) C9 0.0244(6) 0.0253(7) 0.0218(6) -0.0036(5) 0.0029(5) -0.0076(5) C19 0.0248(6) 0.0170(6) 0.0241(6) -0.0001(5) 0.0079(5) -0.0029(5) C24 0.0252(6) 0.0209(6) 0.0240(6) -0.0003(5) 0.0063(5) -0.0031(5) C15 0.0237(6) 0.0206(7) 0.0282(6) -0.0029(5) 0.0039(5) -0.0037(5) C27 0.0281(7) 0.0370(8) 0.0338(7) -0.0003(6) -0.0031(6) 0.0030(6) C21 0.0291(7) 0.0282(7) 0.0337(7) -0.0036(6) 0.0131(5) 0.0008(6) C29 0.0273(7) 0.0296(7) 0.0303(7) -0.0048(6) 0.0079(5) 0.0009(6) C2 0.0224(6) 0.0226(7) 0.0218(6) -0.0015(5) 0.0062(5) -0.0030(5) C8 0.0352(7) 0.0316(8) 0.0247(6) 0.0000(6) 0.0062(5) -0.0097(6) C28 0.0249(7) 0.0326(8) 0.0423(8) -0.0036(6) 0.0053(6) 0.0053(6) C7 0.0322(7) 0.0469(9) 0.0274(7) -0.0042(6) 0.0114(6) -0.0153(7) C26 0.0308(7) 0.0336(8) 0.0261(6) -0.0023(6) 0.0036(5) -0.0002(6) C11 0.0331(7) 0.0272(8) 0.0360(7) 0.0044(6) 0.0035(6) -0.0067(6) C5 0.0248(6) 0.0328(8) 0.0292(7) -0.0042(6) 0.0052(5) -0.0025(6) C16 0.0234(6) 0.0218(7) 0.0257(6) 0.0001(5) 0.0075(5) 0.0014(5) C23 0.0287(7) 0.0394(8) 0.0242(6) -0.0052(6) 0.0041(5) -0.0017(6) C14 0.0306(7) 0.0253(7) 0.0436(8) -0.0020(6) 0.0129(6) -0.0018(6) C6 0.0237(6) 0.0461(9) 0.0332(7) -0.0093(7) 0.0107(5) -0.0063(6) C31 0.0317(7) 0.0387(8) 0.0216(6) 0.0038(6) 0.0096(5) -0.0012(6) C17 0.0237(6) 0.0193(6) 0.0214(6) -0.0007(5) 0.0076(5) -0.0016(5) C22 0.0351(7) 0.0409(9) 0.0264(7) -0.0088(6) 0.0117(6) -0.0013(7) C1 0.0219(6) 0.0273(7) 0.0249(6) -0.0030(6) 0.0065(5) -0.0002(5) C12 0.0350(8) 0.0206(7) 0.0533(9) 0.0041(7) 0.0016(7) 0.0003(6) C32 0.0342(8) 0.0520(10) 0.0302(7) 0.0017(7) 0.0152(6) 0.0006(7) C13 0.0320(7) 0.0249(8) 0.0576(9) -0.0036(7) 0.0114(7) 0.0021(6) C33 0.0450(9) 0.0558(11) 0.0521(10) -0.0121(9) 0.0186(8) 0.0082(8) _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 N1 C1 1.3857(17) . ? N1 C16 1.3899(16) . ? N1 C31 1.4677(15) . ? O2 C16 1.2079(15) . ? O1 C1 1.2084(15) . ? C4 C5 1.3970(18) . ? C4 C9 1.4011(19) . ? C4 C3 1.5047(17) . ? C20 C21 1.3841(18) . ? C20 C19 1.3952(17) . ? C20 H20 0.9500 . ? C30 C29 1.3963(18) . ? C30 C25 1.4015(17) . ? C30 C17 1.5030(17) . ? C18 C19 1.5044(16) . ? C18 C17 1.5634(16) . ? C18 C3 1.5823(18) . ? C18 H18 1.0000 . ? C3 C2 1.5656(17) . ? C3 H3 1.0000 . ? C25 C26 1.4020(18) . ? C25 C24 1.4895(17) . ? C10 C11 1.4036(19) . ? C10 C15 1.4040(17) . ? C10 C9 1.4884(18) . ? C9 C8 1.4068(17) . ? C19 C24 1.4032(17) . ? C24 C23 1.4043(17) . ? C15 C14 1.3952(18) . ? C15 C2 1.5023(18) . ? C27 C26 1.3814(19) . ? C27 C28 1.382(2) . ? C27 H27 0.9500 . ? C21 C22 1.380(2) . ? C21 H21 0.9500 . ? C29 C28 1.3816(19) . ? C29 H29 0.9500 . ? C2 C1 1.5254(16) . ? C2 C17 1.5755(17) . ? C8 C7 1.382(2) . ? C8 H8 0.9500 . ? C28 H28 0.9500 . ? C7 C6 1.381(2) . ? C7 H7 0.9500 . ? C26 H26 0.9500 . ? C11 C12 1.381(2) . ? C11 H11 0.9500 . ? C5 C6 1.3858(19) . ? C5 H5 0.9500 . ? C16 C17 1.5238(16) . ? C23 C22 1.3830(19) . ? C23 H23 0.9500 . ? C14 C13 1.380(2) . ? C14 H14 0.9500 . ? C6 H6 0.9500 . ? C31 C32 1.5246(18) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C22 H22 0.9500 . ? C12 C13 1.379(2) . ? C12 H12 0.9500 . ? C32 C33 1.513(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C13 H13 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 C1 N1 C16 113.99(10) . . ? C1 N1 C31 123.14(11) . . ? C16 N1 C31 122.68(11) . . ? C5 C4 C9 119.93(11) . . ? C5 C4 C3 117.98(12) . . ? C9 C4 C3 122.09(11) . . ? C21 C20 C19 121.35(12) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C29 C30 C25 119.79(12) . . ? C29 C30 C17 118.43(11) . . ? C25 C30 C17 121.77(11) . . ? C19 C18 C17 116.65(10) . . ? C19 C18 C3 119.14(10) . . ? C17 C18 C3 90.04(9) . . ? C19 C18 H18 109.8 . . ? C17 C18 H18 109.8 . . ? C3 C18 H18 109.8 . . ? C4 C3 C2 116.20(10) . . ? C4 C3 C18 117.61(10) . . ? C2 C3 C18 89.65(9) . . ? C4 C3 H3 110.6 . . ? C2 C3 H3 110.6 . . ? C18 C3 H3 110.6 . . ? C26 C25 C30 117.68(12) . . ? C26 C25 C24 121.35(11) . . ? C30 C25 C24 120.96(11) . . ? C11 C10 C15 117.74(12) . . ? C11 C10 C9 121.24(12) . . ? C15 C10 C9 120.78(12) . . ? C4 C9 C8 117.80(12) . . ? C4 C9 C10 120.96(11) . . ? C8 C9 C10 121.06(12) . . ? C20 C19 C24 119.79(11) . . ? C20 C19 C18 118.05(11) . . ? C24 C19 C18 122.12(11) . . ? C19 C24 C23 117.76(12) . . ? C19 C24 C25 120.96(11) . . ? C23 C24 C25 121.23(11) . . ? C14 C15 C10 119.50(12) . . ? C14 C15 C2 119.35(11) . . ? C10 C15 C2 121.13(11) . . ? C26 C27 C28 120.08(13) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C20 C21 C22 119.30(12) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C28 C29 C30 121.47(12) . . ? C28 C29 H29 119.3 . . ? C30 C29 H29 119.3 . . ? C15 C2 C1 112.13(10) . . ? C15 C2 C3 117.52(10) . . ? C1 C2 C3 110.94(10) . . ? C15 C2 C17 119.73(10) . . ? C1 C2 C17 103.92(10) . . ? C3 C2 C17 90.21(9) . . ? C7 C8 C9 121.47(14) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C29 C28 C27 119.10(13) . . ? C29 C28 H28 120.5 . . ? C27 C28 H28 120.5 . . ? C6 C7 C8 120.35(12) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C27 C26 C25 121.85(12) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C12 C11 C10 121.80(13) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C6 C5 C4 121.17(13) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? O2 C16 N1 124.04(11) . . ? O2 C16 C17 127.48(11) . . ? N1 C16 C17 108.46(10) . . ? C22 C23 C24 121.71(12) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C13 C14 C15 121.59(13) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C7 C6 C5 119.18(13) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C31 C32 113.41(11) . . ? N1 C31 H31A 108.9 . . ? C32 C31 H31A 108.9 . . ? N1 C31 H31B 108.9 . . ? C32 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? C30 C17 C16 111.41(10) . . ? C30 C17 C18 117.50(10) . . ? C16 C17 C18 111.08(10) . . ? C30 C17 C2 120.10(10) . . ? C16 C17 C2 104.60(9) . . ? C18 C17 C2 89.98(9) . . ? C21 C22 C23 120.07(12) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? O1 C1 N1 124.30(11) . . ? O1 C1 C2 126.77(12) . . ? N1 C1 C2 108.92(10) . . ? C11 C12 C13 120.02(14) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C33 C32 C31 113.90(13) . . ? C33 C32 H32A 108.8 . . ? C31 C32 H32A 108.8 . . ? C33 C32 H32B 108.8 . . ? C31 C32 H32B 108.8 . . ? H32A C32 H32B 107.7 . . ? C14 C13 C12 119.30(14) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.239 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.038 #===END data_3a(a0601121mas) _database_code_depnum_ccdc_archive 'CCDC 606846' #TrackingRef 'CIF_kohmoto_compound_1a-3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H25 N O2' _chemical_formula_weight 467.54 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.4729(12) _cell_length_b 13.3772(13) _cell_length_c 13.8882(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2317.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 2983 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 23.69 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_T_max 0.9836 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13053 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.20 _reflns_number_total 5198 _reflns_number_gt 4339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^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 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 -0.8(12) _refine_ls_number_reflns 5198 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 N1 N 0.08477(11) 0.71888(11) 0.23414(10) 0.0230(3) Uani 1 1 d . . . C24 C 0.22455(13) 0.80168(13) -0.10172(12) 0.0213(4) Uani 1 1 d . . . C30 C 0.15803(13) 0.90407(12) 0.03884(11) 0.0207(4) Uani 1 1 d . . . C23 C 0.25816(14) 0.79866(14) -0.19819(12) 0.0259(4) Uani 1 1 d . . . H23 H 0.2687 0.8595 -0.2321 0.031 Uiso 1 1 calc R . . C25 C 0.20846(13) 0.89943(12) -0.05159(12) 0.0210(4) Uani 1 1 d . . . C19 C 0.20600(12) 0.71065(12) -0.05495(11) 0.0196(4) Uani 1 1 d . . . C18 C 0.16922(13) 0.70847(12) 0.04896(11) 0.0194(3) Uani 1 1 d . . . H18 H 0.2260 0.6830 0.0935 0.023 Uiso 1 1 calc R . . C21 C 0.26238(15) 0.61942(14) -0.19655(12) 0.0289(4) Uani 1 1 d . . . H21 H 0.2764 0.5578 -0.2281 0.035 Uiso 1 1 calc R . . C17 C 0.11951(13) 0.80884(13) 0.08402(11) 0.0209(4) Uani 1 1 d . . . C16 C 0.12859(13) 0.80524(13) 0.19337(12) 0.0220(4) Uani 1 1 d . . . C20 C 0.22795(14) 0.62075(13) -0.10193(12) 0.0251(4) Uani 1 1 d . . . H20 H 0.2191 0.5594 -0.0683 0.030 Uiso 1 1 calc R . . C1 C 0.04661(14) 0.64045(13) 0.17792(12) 0.0232(4) Uani 1 1 d . . . C2 C 0.05514(13) 0.66018(13) 0.06989(11) 0.0219(4) Uani 1 1 d . . . C29 C 0.13703(13) 0.99665(13) 0.08081(12) 0.0252(4) Uani 1 1 d . . . H29 H 0.1010 0.9999 0.1410 0.030 Uiso 1 1 calc R . . C9 C -0.05546(14) 0.70785(15) -0.10726(13) 0.0292(4) Uani 1 1 d . . . C31 C 0.07263(14) 0.71335(14) 0.33964(11) 0.0261(4) Uani 1 1 d . . . H31A H 0.0009 0.6858 0.3546 0.031 Uiso 1 1 calc R . . H31B H 0.0758 0.7819 0.3663 0.031 Uiso 1 1 calc R . . C27 C 0.22172(15) 1.07997(14) -0.05178(13) 0.0299(4) Uani 1 1 d . . . H27 H 0.2444 1.1399 -0.0823 0.036 Uiso 1 1 calc R . . C28 C 0.16840(15) 1.08392(13) 0.03526(13) 0.0276(4) Uani 1 1 d . . . H28 H 0.1532 1.1468 0.0640 0.033 Uiso 1 1 calc R . . C8 C -0.08880(15) 0.73307(18) -0.20067(14) 0.0404(5) Uani 1 1 d . . . H8 H -0.1023 0.6814 -0.2460 0.049 Uiso 1 1 calc R . . C3 C 0.00480(13) 0.76625(12) 0.05687(12) 0.0222(4) Uani 1 1 d . . . H3 H -0.0504 0.7816 0.1069 0.027 Uiso 1 1 calc R . . C26 C 0.24193(14) 0.98870(14) -0.09420(12) 0.0261(4) Uani 1 1 d . . . H26 H 0.2794 0.9865 -0.1537 0.031 Uiso 1 1 calc R . . C4 C -0.03440(13) 0.78668(14) -0.04314(12) 0.0258(4) Uani 1 1 d . . . C5 C -0.05397(14) 0.88507(15) -0.07091(13) 0.0320(4) Uani 1 1 d . . . H5 H -0.0444 0.9375 -0.0255 0.038 Uiso 1 1 calc R . . C10 C -0.04132(14) 0.60171(15) -0.07740(12) 0.0291(4) Uani 1 1 d . . . C15 C 0.01471(14) 0.57722(13) 0.00713(12) 0.0256(4) Uani 1 1 d . . . C22 C 0.27616(14) 0.70897(14) -0.24468(12) 0.0293(4) Uani 1 1 d . . . H22 H 0.2981 0.7088 -0.3102 0.035 Uiso 1 1 calc R . . C11 C -0.08091(15) 0.52344(17) -0.13388(14) 0.0378(5) Uani 1 1 d . . . H11 H -0.1229 0.5383 -0.1891 0.045 Uiso 1 1 calc R . . C14 C 0.03723(15) 0.47740(14) 0.02857(13) 0.0309(4) Uani 1 1 d . . . H14 H 0.0776 0.4613 0.0845 0.037 Uiso 1 1 calc R . . C12 C -0.06011(17) 0.42479(17) -0.11085(14) 0.0413(5) Uani 1 1 d . . . H12 H -0.0880 0.3727 -0.1500 0.050 Uiso 1 1 calc R . . C7 C -0.10241(16) 0.83101(19) -0.22800(15) 0.0458(6) Uani 1 1 d . . . H7 H -0.1227 0.8460 -0.2923 0.055 Uiso 1 1 calc R . . C13 C 0.00115(17) 0.40193(15) -0.03108(13) 0.0376(5) Uani 1 1 d . . . H13 H 0.0185 0.3343 -0.0172 0.045 Uiso 1 1 calc R . . C6 C -0.08701(15) 0.90775(18) -0.16332(15) 0.0434(6) Uani 1 1 d . . . H6 H -0.0989 0.9752 -0.1820 0.052 Uiso 1 1 calc R . . C32 C 0.15639(18) 0.65020(15) 0.38934(12) 0.0380(5) Uani 1 1 d . . . H32A H 0.2285 0.6750 0.3717 0.046 Uiso 1 1 calc R . . H32B H 0.1503 0.5803 0.3665 0.046 Uiso 1 1 calc R . . C33 C 0.14466(18) 0.65220(15) 0.49857(12) 0.0376(5) Uani 1 1 d . . . H33A H 0.0722 0.6307 0.5163 0.056 Uiso 1 1 calc R . . H33B H 0.1570 0.7203 0.5221 0.056 Uiso 1 1 calc R . . H33C H 0.1973 0.6068 0.5275 0.056 Uiso 1 1 calc R . . O1 O 0.00818(11) 0.56672(9) 0.21460(8) 0.0328(3) Uani 1 1 d . . . O2 O 0.17011(10) 0.86826(8) 0.24333(8) 0.0286(3) 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 N1 0.0250(8) 0.0274(8) 0.0167(7) -0.0005(6) 0.0014(6) -0.0025(6) C24 0.0163(8) 0.0273(9) 0.0202(8) 0.0001(7) -0.0007(7) 0.0006(7) C30 0.0164(8) 0.0248(9) 0.0208(8) 0.0015(7) -0.0009(7) -0.0018(7) C23 0.0270(9) 0.0313(10) 0.0193(8) 0.0033(8) 0.0003(7) -0.0004(8) C25 0.0151(8) 0.0248(9) 0.0232(8) -0.0008(7) -0.0021(7) -0.0001(7) C19 0.0131(8) 0.0256(9) 0.0200(8) -0.0016(7) 0.0007(7) -0.0006(7) C18 0.0195(8) 0.0213(8) 0.0174(8) -0.0004(7) -0.0017(7) -0.0016(7) C21 0.0315(10) 0.0299(10) 0.0252(9) -0.0064(8) 0.0015(8) -0.0011(8) C17 0.0173(8) 0.0273(9) 0.0181(8) -0.0001(7) 0.0008(7) -0.0003(7) C16 0.0194(8) 0.0271(9) 0.0194(8) -0.0016(8) 0.0015(7) 0.0019(7) C20 0.0244(9) 0.0251(10) 0.0258(9) 0.0002(7) -0.0006(8) -0.0012(7) C1 0.0203(9) 0.0260(9) 0.0234(9) 0.0014(8) 0.0007(7) -0.0020(7) C2 0.0177(9) 0.0291(10) 0.0189(8) 0.0014(7) -0.0002(7) -0.0034(7) C29 0.0216(9) 0.0300(10) 0.0240(9) -0.0005(8) 0.0040(7) 0.0010(7) C9 0.0153(8) 0.0503(12) 0.0221(8) 0.0032(9) 0.0010(7) -0.0048(8) C31 0.0285(10) 0.0322(10) 0.0178(8) 0.0012(8) 0.0019(7) -0.0012(8) C27 0.0324(11) 0.0261(10) 0.0313(10) 0.0037(8) 0.0031(8) -0.0036(8) C28 0.0275(10) 0.0224(9) 0.0329(10) -0.0035(8) 0.0030(8) 0.0006(8) C8 0.0246(10) 0.0720(16) 0.0248(10) 0.0033(10) -0.0029(8) -0.0103(10) C3 0.0179(8) 0.0292(9) 0.0194(8) 0.0020(7) 0.0021(7) -0.0025(7) C26 0.0264(9) 0.0289(10) 0.0232(9) 0.0016(8) 0.0036(7) -0.0024(8) C4 0.0146(8) 0.0408(11) 0.0219(8) 0.0048(8) 0.0011(7) -0.0014(8) C5 0.0179(9) 0.0453(12) 0.0327(10) 0.0103(9) -0.0016(8) -0.0019(8) C10 0.0188(9) 0.0460(11) 0.0226(9) -0.0055(9) 0.0041(7) -0.0057(8) C15 0.0220(10) 0.0331(10) 0.0216(8) -0.0011(8) 0.0039(7) -0.0074(8) C22 0.0322(10) 0.0367(11) 0.0191(8) -0.0049(8) 0.0012(8) 0.0002(9) C11 0.0248(10) 0.0590(14) 0.0296(10) -0.0112(10) 0.0019(8) -0.0091(9) C14 0.0305(10) 0.0354(11) 0.0270(9) -0.0027(8) 0.0073(8) -0.0075(8) C12 0.0349(12) 0.0532(14) 0.0358(11) -0.0217(10) 0.0085(9) -0.0176(10) C7 0.0255(11) 0.0848(18) 0.0271(11) 0.0235(11) -0.0049(9) -0.0091(10) C13 0.0396(12) 0.0345(11) 0.0389(11) -0.0094(9) 0.0135(9) -0.0119(10) C6 0.0224(10) 0.0631(15) 0.0447(12) 0.0239(12) -0.0051(9) -0.0051(10) C32 0.0459(12) 0.0438(12) 0.0242(10) 0.0020(9) -0.0010(9) 0.0126(10) C33 0.0508(14) 0.0367(11) 0.0253(10) 0.0044(9) -0.0067(10) 0.0058(10) O1 0.0407(8) 0.0332(7) 0.0246(6) 0.0043(6) 0.0028(6) -0.0110(6) O2 0.0331(7) 0.0299(7) 0.0227(6) -0.0029(5) -0.0006(6) -0.0033(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 N1 C1 1.392(2) . ? N1 C16 1.398(2) . ? N1 C31 1.475(2) . ? C24 C19 1.399(2) . ? C24 C23 1.404(2) . ? C24 C25 1.495(2) . ? C30 C29 1.394(2) . ? C30 C25 1.406(2) . ? C30 C17 1.499(2) . ? C23 C22 1.381(2) . ? C23 H23 0.9500 . ? C25 C26 1.397(2) . ? C19 C20 1.395(2) . ? C19 C18 1.515(2) . ? C18 C17 1.557(2) . ? C18 C2 1.590(2) . ? C18 H18 1.0000 . ? C21 C22 1.383(2) . ? C21 C20 1.383(2) . ? C21 H21 0.9500 . ? C17 C16 1.524(2) . ? C17 C3 1.585(2) . ? C16 O2 1.2084(19) . ? C20 H20 0.9500 . ? C1 O1 1.2092(19) . ? C1 C2 1.527(2) . ? C2 C15 1.499(2) . ? C2 C3 1.562(2) . ? C29 C28 1.384(2) . ? C29 H29 0.9500 . ? C9 C8 1.403(3) . ? C9 C4 1.405(3) . ? C9 C10 1.490(3) . ? C31 C32 1.511(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C27 C26 1.379(2) . ? C27 C28 1.381(2) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C8 C7 1.374(3) . ? C8 H8 0.9500 . ? C3 C4 1.498(2) . ? C3 H3 1.0000 . ? C26 H26 0.9500 . ? C4 C5 1.393(3) . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C10 C11 1.398(3) . ? C10 C15 1.405(2) . ? C15 C14 1.397(2) . ? C22 H22 0.9500 . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C14 C13 1.381(2) . ? C14 H14 0.9500 . ? C12 C13 1.380(3) . ? C12 H12 0.9500 . ? C7 C6 1.378(3) . ? C7 H7 0.9500 . ? C13 H13 0.9500 . ? C6 H6 0.9500 . ? C32 C33 1.524(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 C1 N1 C16 121.97(13) . . ? C1 N1 C31 118.98(14) . . ? C16 N1 C31 118.95(14) . . ? C19 C24 C23 117.85(16) . . ? C19 C24 C25 121.52(14) . . ? C23 C24 C25 120.63(15) . . ? C29 C30 C25 119.80(15) . . ? C29 C30 C17 121.33(14) . . ? C25 C30 C17 118.67(14) . . ? C22 C23 C24 121.30(16) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C26 C25 C30 118.33(15) . . ? C26 C25 C24 120.69(14) . . ? C30 C25 C24 120.97(15) . . ? C20 C19 C24 120.04(15) . . ? C20 C19 C18 119.23(15) . . ? C24 C19 C18 120.60(14) . . ? C19 C18 C17 113.70(13) . . ? C19 C18 C2 116.95(13) . . ? C17 C18 C2 86.37(12) . . ? C19 C18 H18 112.5 . . ? C17 C18 H18 112.5 . . ? C2 C18 H18 112.5 . . ? C22 C21 C20 119.14(16) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C30 C17 C16 114.84(14) . . ? C30 C17 C18 118.31(13) . . ? C16 C17 C18 104.77(13) . . ? C30 C17 C3 119.67(13) . . ? C16 C17 C3 107.02(13) . . ? C18 C17 C3 88.58(12) . . ? O2 C16 N1 120.77(14) . . ? O2 C16 C17 125.60(16) . . ? N1 C16 C17 113.63(14) . . ? C21 C20 C19 121.10(16) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? O1 C1 N1 120.94(15) . . ? O1 C1 C2 125.62(15) . . ? N1 C1 C2 113.40(14) . . ? C15 C2 C1 114.84(13) . . ? C15 C2 C3 118.04(14) . . ? C1 C2 C3 104.05(13) . . ? C15 C2 C18 119.72(14) . . ? C1 C2 C18 108.20(13) . . ? C3 C2 C18 88.25(12) . . ? C28 C29 C30 120.34(15) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C8 C9 C4 117.44(19) . . ? C8 C9 C10 121.44(18) . . ? C4 C9 C10 121.12(16) . . ? N1 C31 C32 114.27(15) . . ? N1 C31 H31A 108.7 . . ? C32 C31 H31A 108.7 . . ? N1 C31 H31B 108.7 . . ? C32 C31 H31B 108.7 . . ? H31A C31 H31B 107.6 . . ? C26 C27 C28 119.74(17) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C27 C28 C29 120.27(16) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C7 C8 C9 121.4(2) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C4 C3 C2 113.85(14) . . ? C4 C3 C17 116.72(14) . . ? C2 C3 C17 86.34(12) . . ? C4 C3 H3 112.5 . . ? C2 C3 H3 112.5 . . ? C17 C3 H3 112.5 . . ? C27 C26 C25 121.42(16) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C5 C4 C9 120.06(16) . . ? C5 C4 C3 119.10(16) . . ? C9 C4 C3 120.79(17) . . ? C6 C5 C4 121.12(19) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C11 C10 C15 118.02(18) . . ? C11 C10 C9 121.05(17) . . ? C15 C10 C9 120.91(16) . . ? C14 C15 C10 120.08(16) . . ? C14 C15 C2 121.09(15) . . ? C10 C15 C2 118.73(16) . . ? C23 C22 C21 120.44(15) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C12 C11 C10 121.24(19) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C14 C15 120.36(18) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C13 C12 C11 120.08(18) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C8 C7 C6 120.86(18) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C12 C13 C14 119.99(19) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C7 C6 C5 118.9(2) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C31 C32 C33 112.25(16) . . ? C31 C32 H32A 109.2 . . ? C33 C32 H32A 109.2 . . ? C31 C32 H32B 109.2 . . ? C33 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.171 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.046 #===END # Attachment 'CIF_kohmoto_compound_1a-3a.cif' data_1a(a0902042mas) _database_code_depnum_ccdc_archive 'CCDC 759325' #TrackingRef 'CIF_kohmoto_compound_1a-3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H25 N O2' _chemical_formula_weight 467.54 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 Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' 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' _cell_length_a 9.4894(18) _cell_length_b 27.726(5) _cell_length_c 9.0631(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2384.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200 _cell_measurement_reflns_used 3032 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 26.76 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11320 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.24 _reflns_number_total 4220 _reflns_number_gt 3424 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0391P)^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 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 -0.9(12) _refine_ls_number_reflns 4220 _refine_ls_number_parameters 326 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 C1 C 0.78720(18) 0.40545(6) -0.0023(2) 0.0368(4) Uani 1 1 d . . . C2 C 0.82371(19) 0.36721(6) 0.1087(2) 0.0361(4) Uani 1 1 d . . . C3 C 0.75899(19) 0.36826(6) 0.2415(2) 0.0402(5) Uani 1 1 d . . . H3 H 0.6920 0.3930 0.2604 0.048 Uiso 1 1 calc R . . C4 C 0.7871(2) 0.33377(6) 0.3543(2) 0.0416(5) Uani 1 1 d . . . C5 C 0.7161(2) 0.33560(7) 0.4901(2) 0.0517(6) Uani 1 1 d . . . H5 H 0.6446 0.3591 0.5049 0.062 Uiso 1 1 calc R . . C6 C 0.7482(3) 0.30409(8) 0.6014(3) 0.0623(7) Uani 1 1 d . . . H6 H 0.6994 0.3057 0.6928 0.075 Uiso 1 1 calc R . . C7 C 0.8530(3) 0.26966(8) 0.5794(3) 0.0656(7) Uani 1 1 d . . . H7 H 0.8755 0.2477 0.6563 0.079 Uiso 1 1 calc R . . C8 C 0.9242(2) 0.26720(7) 0.4476(3) 0.0559(6) Uani 1 1 d . . . H8 H 0.9955 0.2435 0.4350 0.067 Uiso 1 1 calc R . . C9 C 0.8937(2) 0.29909(6) 0.3305(2) 0.0430(5) Uani 1 1 d . . . C10 C 0.9655(2) 0.29774(6) 0.1895(2) 0.0401(5) Uani 1 1 d . . . C11 C 1.0773(2) 0.26538(6) 0.1609(3) 0.0518(6) Uani 1 1 d . . . H11 H 1.1089 0.2445 0.2371 0.062 Uiso 1 1 calc R . . C12 C 1.1407(2) 0.26352(7) 0.0259(3) 0.0554(6) Uani 1 1 d . . . H12 H 1.2169 0.2419 0.0101 0.066 Uiso 1 1 calc R . . C13 C 1.0952(2) 0.29287(6) -0.0885(3) 0.0508(5) Uani 1 1 d . . . H13 H 1.1367 0.2901 -0.1835 0.061 Uiso 1 1 calc R . . C14 C 0.98972(19) 0.32602(6) -0.0639(2) 0.0425(5) Uani 1 1 d . . . H14 H 0.9602 0.3466 -0.1418 0.051 Uiso 1 1 calc R . . C15 C 0.92562(18) 0.32977(6) 0.0746(2) 0.0370(4) Uani 1 1 d . . . C16 C 0.8847(2) 0.46797(6) 0.1589(2) 0.0384(4) Uani 1 1 d . . . C17 C 1.02070(19) 0.44063(6) 0.1646(2) 0.0368(4) Uani 1 1 d . . . C18 C 1.09588(19) 0.43700(6) 0.0385(2) 0.0364(4) Uani 1 1 d . . . H18 H 1.0624 0.4527 -0.0479 0.044 Uiso 1 1 calc R . . C19 C 1.22432(19) 0.41017(6) 0.0313(2) 0.0385(4) Uani 1 1 d . . . C20 C 1.29913(19) 0.40701(7) -0.1009(2) 0.0451(5) Uani 1 1 d . . . H20 H 1.2695 0.4253 -0.1838 0.054 Uiso 1 1 calc R . . C21 C 1.4153(2) 0.37759(7) -0.1123(3) 0.0529(6) Uani 1 1 d . . . H21 H 1.4656 0.3753 -0.2027 0.064 Uiso 1 1 calc R . . C22 C 1.4582(2) 0.35122(7) 0.0106(3) 0.0573(6) Uani 1 1 d . . . H22 H 1.5377 0.3305 0.0030 0.069 Uiso 1 1 calc R . . C23 C 1.3884(2) 0.35453(7) 0.1409(3) 0.0532(6) Uani 1 1 d . . . H23 H 1.4204 0.3361 0.2227 0.064 Uiso 1 1 calc R . . C24 C 1.2695(2) 0.38470(6) 0.1580(2) 0.0421(5) Uani 1 1 d . . . C25 C 1.1930(2) 0.38992(6) 0.2951(2) 0.0436(5) Uani 1 1 d . . . C26 C 1.2328(3) 0.36603(7) 0.4263(3) 0.0584(6) Uani 1 1 d . . . H26 H 1.3132 0.3456 0.4254 0.070 Uiso 1 1 calc R . . C27 C 1.1587(3) 0.37155(8) 0.5545(3) 0.0654(7) Uani 1 1 d . . . H27 H 1.1879 0.3549 0.6409 0.079 Uiso 1 1 calc R . . C28 C 1.0412(3) 0.40129(8) 0.5595(2) 0.0594(6) Uani 1 1 d . . . H28 H 0.9910 0.4054 0.6493 0.071 Uiso 1 1 calc R . . C29 C 0.9980(2) 0.42461(7) 0.4347(2) 0.0506(5) Uani 1 1 d . . . H29 H 0.9172 0.4448 0.4387 0.061 Uiso 1 1 calc R . . C30 C 1.0706(2) 0.41938(6) 0.3009(2) 0.0403(5) Uani 1 1 d . . . C31 C 0.6860(2) 0.48849(6) -0.0040(2) 0.0452(5) Uani 1 1 d . . . H31A H 0.6588 0.4796 -0.1059 0.054 Uiso 1 1 calc R . . H31B H 0.7312 0.5206 -0.0078 0.054 Uiso 1 1 calc R . . C32 C 0.5547(2) 0.49160(7) 0.0899(3) 0.0504(5) Uani 1 1 d . . . H32A H 0.5819 0.4988 0.1931 0.060 Uiso 1 1 calc R . . H32B H 0.5061 0.4600 0.0890 0.060 Uiso 1 1 calc R . . C33 C 0.4542(3) 0.53034(8) 0.0352(3) 0.0701(7) Uani 1 1 d . . . H33A H 0.5040 0.5612 0.0289 0.105 Uiso 1 1 calc R . . H33B H 0.3750 0.5333 0.1041 0.105 Uiso 1 1 calc R . . H33C H 0.4186 0.5214 -0.0626 0.105 Uiso 1 1 calc R . . N1 N 0.78903(16) 0.45298(5) 0.05173(17) 0.0378(4) Uani 1 1 d . . . O1 O 0.74625(14) 0.39659(4) -0.12606(14) 0.0453(3) Uani 1 1 d . . . O2 O 0.86225(15) 0.50384(4) 0.23285(17) 0.0517(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 0.0286(10) 0.0392(10) 0.0426(12) -0.0027(8) -0.0002(9) 0.0003(7) C2 0.0339(10) 0.0288(9) 0.0457(12) -0.0001(8) -0.0079(9) -0.0020(7) C3 0.0389(11) 0.0326(9) 0.0491(12) -0.0012(9) -0.0027(10) -0.0036(8) C4 0.0455(12) 0.0337(9) 0.0457(12) 0.0005(8) -0.0050(10) -0.0120(8) C5 0.0581(14) 0.0455(11) 0.0515(14) 0.0033(10) 0.0001(11) -0.0139(10) C6 0.0825(18) 0.0559(13) 0.0485(14) 0.0066(11) 0.0012(12) -0.0205(13) C7 0.0862(19) 0.0511(13) 0.0596(17) 0.0178(12) -0.0186(15) -0.0164(13) C8 0.0646(16) 0.0400(11) 0.0631(15) 0.0093(11) -0.0162(13) -0.0049(10) C9 0.0472(12) 0.0296(9) 0.0524(14) 0.0035(9) -0.0140(10) -0.0112(8) C10 0.0385(11) 0.0257(9) 0.0561(14) -0.0015(8) -0.0099(9) -0.0035(8) C11 0.0473(13) 0.0312(10) 0.0768(17) 0.0043(10) -0.0141(12) 0.0025(9) C12 0.0423(12) 0.0353(10) 0.0885(18) -0.0037(11) -0.0043(13) 0.0083(9) C13 0.0435(12) 0.0371(10) 0.0717(16) -0.0071(11) 0.0070(12) 0.0016(9) C14 0.0407(11) 0.0310(9) 0.0558(13) -0.0033(9) -0.0031(10) 0.0003(8) C15 0.0334(10) 0.0283(9) 0.0492(13) -0.0027(8) -0.0042(9) -0.0029(7) C16 0.0439(11) 0.0314(9) 0.0400(11) 0.0024(8) 0.0022(9) -0.0026(8) C17 0.0398(11) 0.0284(9) 0.0422(11) -0.0001(8) -0.0061(9) -0.0044(8) C18 0.0369(10) 0.0303(9) 0.0418(11) 0.0046(8) -0.0064(9) -0.0026(7) C19 0.0339(10) 0.0309(9) 0.0506(12) 0.0040(8) -0.0088(9) -0.0054(7) C20 0.0361(11) 0.0413(10) 0.0579(15) 0.0034(9) -0.0044(10) -0.0016(8) C21 0.0377(12) 0.0478(11) 0.0734(17) 0.0034(11) 0.0012(11) 0.0022(9) C22 0.0357(12) 0.0466(12) 0.0895(19) 0.0091(12) -0.0118(13) 0.0051(9) C23 0.0394(12) 0.0454(11) 0.0749(17) 0.0152(11) -0.0151(12) -0.0004(9) C24 0.0353(11) 0.0341(10) 0.0570(13) 0.0088(9) -0.0169(10) -0.0087(8) C25 0.0491(12) 0.0322(9) 0.0496(13) 0.0071(9) -0.0184(10) -0.0113(9) C26 0.0679(16) 0.0455(11) 0.0617(16) 0.0123(11) -0.0262(14) -0.0102(11) C27 0.097(2) 0.0537(13) 0.0455(15) 0.0140(11) -0.0233(14) -0.0191(13) C28 0.0866(18) 0.0520(13) 0.0397(13) 0.0046(10) -0.0116(12) -0.0212(12) C29 0.0643(14) 0.0440(11) 0.0435(12) 0.0012(10) -0.0073(12) -0.0174(10) C30 0.0468(12) 0.0327(9) 0.0413(11) 0.0014(8) -0.0115(10) -0.0141(8) C31 0.0500(12) 0.0351(10) 0.0503(13) 0.0030(9) -0.0043(10) 0.0114(8) C32 0.0434(12) 0.0497(11) 0.0580(14) 0.0021(11) -0.0041(11) 0.0070(9) C33 0.0645(16) 0.0726(15) 0.0733(17) -0.0046(13) -0.0042(14) 0.0314(13) N1 0.0400(8) 0.0309(7) 0.0427(9) -0.0007(7) -0.0026(7) 0.0048(6) O1 0.0461(8) 0.0463(7) 0.0436(9) -0.0035(6) -0.0073(7) 0.0042(6) O2 0.0624(10) 0.0381(7) 0.0547(9) -0.0111(7) 0.0000(8) 0.0024(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 C1 O1 1.212(2) . ? C1 N1 1.406(2) . ? C1 C2 1.502(3) . ? C2 C3 1.351(3) . ? C2 C15 1.452(2) . ? C3 C4 1.425(3) . ? C3 H3 0.9500 . ? C4 C5 1.403(3) . ? C4 C9 1.412(3) . ? C5 C6 1.369(3) . ? C5 H5 0.9500 . ? C6 C7 1.393(3) . ? C6 H6 0.9500 . ? C7 C8 1.374(3) . ? C7 H7 0.9500 . ? C8 C9 1.411(3) . ? C8 H8 0.9500 . ? C9 C10 1.448(3) . ? C10 C11 1.413(3) . ? C10 C15 1.420(3) . ? C11 C12 1.365(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 C14 1.377(3) . ? C13 H13 0.9500 . ? C14 C15 1.398(3) . ? C14 H14 0.9500 . ? C16 O2 1.218(2) . ? C16 N1 1.393(2) . ? C16 C17 1.498(3) . ? C17 C18 1.352(3) . ? C17 C30 1.448(3) . ? C18 C19 1.429(2) . ? C18 H18 0.9500 . ? C19 C20 1.396(3) . ? C19 C24 1.415(3) . ? C20 C21 1.375(3) . ? C20 H20 0.9500 . ? C21 C22 1.393(3) . ? C21 H21 0.9500 . ? C22 C23 1.357(3) . ? C22 H22 0.9500 . ? C23 C24 1.413(3) . ? C23 H23 0.9500 . ? C24 C25 1.446(3) . ? C25 C26 1.413(3) . ? C25 C30 1.421(3) . ? C26 C27 1.367(3) . ? C26 H26 0.9500 . ? C27 C28 1.388(3) . ? C27 H27 0.9500 . ? C28 C29 1.365(3) . ? C28 H28 0.9500 . ? C29 C30 1.402(3) . ? C29 H29 0.9500 . ? C31 N1 1.477(2) . ? C31 C32 1.511(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.520(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 O1 C1 N1 121.09(16) . . ? O1 C1 C2 123.41(16) . . ? N1 C1 C2 115.17(16) . . ? C3 C2 C15 120.51(16) . . ? C3 C2 C1 118.46(16) . . ? C15 C2 C1 121.03(17) . . ? C2 C3 C4 122.65(17) . . ? C2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C5 C4 C9 120.18(18) . . ? C5 C4 C3 120.99(18) . . ? C9 C4 C3 118.75(18) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.4(2) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.5(2) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 117.3(2) . . ? C8 C9 C10 123.42(19) . . ? C4 C9 C10 119.31(17) . . ? C11 C10 C15 117.54(19) . . ? C11 C10 C9 122.11(18) . . ? C15 C10 C9 120.35(16) . . ? C12 C11 C10 121.3(2) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 120.70(19) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.76(19) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C14 C15 C10 119.71(16) . . ? C14 C15 C2 122.29(16) . . ? C10 C15 C2 117.92(17) . . ? O2 C16 N1 120.88(17) . . ? O2 C16 C17 123.03(17) . . ? N1 C16 C17 115.76(15) . . ? C18 C17 C30 121.27(17) . . ? C18 C17 C16 117.60(17) . . ? C30 C17 C16 121.13(17) . . ? C17 C18 C19 121.81(18) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C20 C19 C24 120.76(16) . . ? C20 C19 C18 120.35(17) . . ? C24 C19 C18 118.79(18) . . ? C21 C20 C19 120.65(19) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 119.0(2) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C23 C22 C21 121.20(19) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 121.68(19) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C23 C24 C19 116.64(19) . . ? C23 C24 C25 123.68(18) . . ? C19 C24 C25 119.67(17) . . ? C26 C25 C30 117.2(2) . . ? C26 C25 C24 122.80(19) . . ? C30 C25 C24 120.00(17) . . ? C27 C26 C25 121.7(2) . . ? C27 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C26 C27 C28 120.5(2) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C29 C28 C27 119.7(2) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C28 C29 C30 121.4(2) . . ? C28 C29 H29 119.3 . . ? C30 C29 H29 119.3 . . ? C29 C30 C25 119.54(18) . . ? C29 C30 C17 122.37(18) . . ? C25 C30 C17 117.98(18) . . ? N1 C31 C32 113.01(16) . . ? N1 C31 H31A 109.0 . . ? C32 C31 H31A 109.0 . . ? N1 C31 H31B 109.0 . . ? C32 C31 H31B 109.0 . . ? H31A C31 H31B 107.8 . . ? C31 C32 C33 111.96(18) . . ? C31 C32 H32A 109.2 . . ? C33 C32 H32A 109.2 . . ? C31 C32 H32B 109.2 . . ? C33 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C16 N1 C1 122.04(15) . . ? C16 N1 C31 118.12(14) . . ? C1 N1 C31 119.83(15) . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.108 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.030