# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_masha07 _database_code_depnum_ccdc_archive 'CCDC 923056' #TrackingRef 'web_deposit_cif_file_2_Louis-PhilippeBonhomme-Beaulieu_1359991019.Compound 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 N O' _chemical_formula_weight 259.29 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 17.1888(15) _cell_length_b 7.7634(6) _cell_length_c 19.7711(18) _cell_angle_alpha 90.00 _cell_angle_beta 107.401(4) _cell_angle_gamma 90.00 _cell_volume 2517.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9508 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61638 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5142 _reflns_number_gt 3553 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ATOMS V.5.0' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0948P)^2^+0.6662P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5142 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.11109(7) 0.46019(14) -0.11654(6) 0.0275(3) Uani 1 1 d . . . N1 N 0.30712(7) 0.72248(15) 0.06866(6) 0.0156(3) Uani 1 1 d . . . C1 C 0.23789(9) 0.74223(18) 0.09221(8) 0.0165(3) Uani 1 1 d . . . C2 C 0.23171(9) 0.81935(18) 0.15366(8) 0.0178(3) Uani 1 1 d . . . H2 H 0.2777 0.8698 0.1871 0.021 Uiso 1 1 calc R . . C3 C 0.15571(10) 0.81988(19) 0.16437(8) 0.0208(4) Uani 1 1 d . . . H3 H 0.1496 0.8711 0.2061 0.025 Uiso 1 1 calc R . . C4 C 0.08762(10) 0.74656(19) 0.11496(8) 0.0222(4) Uani 1 1 d . . . H4 H 0.0363 0.7486 0.1239 0.027 Uiso 1 1 calc R . . C5 C 0.09391(9) 0.67128(19) 0.05346(8) 0.0206(3) Uani 1 1 d . . . H5 H 0.0473 0.6231 0.0200 0.025 Uiso 1 1 calc R . . C6 C 0.16998(9) 0.66722(18) 0.04132(7) 0.0167(3) Uani 1 1 d . . . C7 C 0.20134(9) 0.60120(18) -0.01328(7) 0.0166(3) Uani 1 1 d . . . C8 C 0.17832(9) 0.51279(18) -0.08084(8) 0.0191(3) Uani 1 1 d . . . C9 C 0.25664(9) 0.49941(18) -0.10082(8) 0.0186(3) Uani 1 1 d . . . C10 C 0.32137(9) 0.57609(18) -0.04731(7) 0.0171(3) Uani 1 1 d . . . C11 C 0.28320(9) 0.63791(17) 0.00604(7) 0.0153(3) Uani 1 1 d . . . C12 C 0.26911(10) 0.42888(19) -0.16031(8) 0.0230(4) Uani 1 1 d . . . H12 H 0.2254 0.3776 -0.1959 0.028 Uiso 1 1 calc R . . C13 C 0.34757(10) 0.4341(2) -0.16740(8) 0.0248(4) Uani 1 1 d . . . H13 H 0.3573 0.3858 -0.2083 0.030 Uiso 1 1 calc R . . C14 C 0.41104(10) 0.5086(2) -0.11554(8) 0.0230(4) Uani 1 1 d . . . H14 H 0.4639 0.5118 -0.1215 0.028 Uiso 1 1 calc R . . C15 C 0.39889(10) 0.57999(19) -0.05416(8) 0.0203(3) Uani 1 1 d . . . H15 H 0.4429 0.6296 -0.0183 0.024 Uiso 1 1 calc R . . C16 C 0.38862(9) 0.78776(19) 0.10559(7) 0.0176(3) Uani 1 1 d . . . H16B H 0.3851 0.9129 0.1138 0.021 Uiso 1 1 calc R . . H16A H 0.4242 0.7715 0.0749 0.021 Uiso 1 1 calc R . . C17 C 0.42673(8) 0.70101(19) 0.17496(7) 0.0176(3) Uani 1 1 d . . . H17 H 0.4240 0.5791 0.1774 0.021 Uiso 1 1 calc R . . C18 C 0.46414(9) 0.7876(2) 0.23299(8) 0.0235(4) Uani 1 1 d . . . H18B H 0.4675 0.9096 0.2315 0.028 Uiso 1 1 calc R . . H18A H 0.4877 0.7279 0.2762 0.028 Uiso 1 1 calc R . . O1A O 0.39700(6) 0.20942(14) 0.61079(5) 0.0250(3) Uani 1 1 d . . . N1A N 0.19161(7) 0.46680(15) 0.43120(6) 0.0152(3) Uani 1 1 d . . . C1A C 0.18501(9) 0.31687(18) 0.54894(7) 0.0168(3) Uani 1 1 d . . . C2A C 0.10859(10) 0.31446(18) 0.55843(8) 0.0198(3) Uani 1 1 d . . . H2A H 0.0628 0.3620 0.5238 0.024 Uiso 1 1 calc R . . C3A C 0.10047(10) 0.23975(19) 0.62067(8) 0.0212(4) Uani 1 1 d . . . H3A H 0.0484 0.2371 0.6282 0.025 Uiso 1 1 calc R . . C4A C 0.16673(10) 0.17011(19) 0.67109(8) 0.0219(4) Uani 1 1 d . . . H4A H 0.1598 0.1209 0.7129 0.026 Uiso 1 1 calc R . . C5A C 0.24397(10) 0.17129(19) 0.66129(8) 0.0206(4) Uani 1 1 d . . . H5A H 0.2896 0.1230 0.6959 0.025 Uiso 1 1 calc R . . C6A C 0.25253(9) 0.24339(18) 0.60081(7) 0.0181(3) Uani 1 1 d . . . C7A C 0.32839(9) 0.26020(18) 0.57738(7) 0.0181(3) Uani 1 1 d . . . C8A C 0.30125(9) 0.34879(18) 0.51001(7) 0.0165(3) Uani 1 1 d . . . C9A C 0.21912(9) 0.38176(17) 0.49343(7) 0.0153(3) Uani 1 1 d . . . C10A C 0.32902(9) 0.41914(17) 0.45403(7) 0.0155(3) Uani 1 1 d . . . C11A C 0.40387(9) 0.43005(18) 0.43983(8) 0.0184(3) Uani 1 1 d . . . H11A H 0.4518 0.3827 0.4718 0.022 Uiso 1 1 calc R . . C12A C 0.40669(9) 0.51123(19) 0.37830(8) 0.0192(3) Uani 1 1 d . . . H12A H 0.4571 0.5195 0.3681 0.023 Uiso 1 1 calc R . . C13A C 0.33624(9) 0.58152(19) 0.33085(8) 0.0179(3) Uani 1 1 d . . . H13A H 0.3399 0.6361 0.2889 0.021 Uiso 1 1 calc R . . C14A C 0.26150(9) 0.57327(18) 0.34366(7) 0.0165(3) Uani 1 1 d . . . H14A H 0.2139 0.6213 0.3115 0.020 Uiso 1 1 calc R . . C15A C 0.25907(8) 0.49187(18) 0.40542(7) 0.0152(3) Uani 1 1 d . . . C16A C 0.10888(8) 0.52862(19) 0.39675(7) 0.0165(3) Uani 1 1 d . . . H16D H 0.1101 0.6554 0.3916 0.020 Uiso 1 1 calc R . . H16C H 0.0741 0.5018 0.4273 0.020 Uiso 1 1 calc R . . C17A C 0.07196(8) 0.44946(19) 0.32523(7) 0.0181(3) Uani 1 1 d . . . H17A H 0.0758 0.3283 0.3203 0.022 Uiso 1 1 calc R . . C18A C 0.03445(9) 0.5411(2) 0.26906(8) 0.0247(4) Uani 1 1 d . . . H18D H 0.0300 0.6624 0.2729 0.030 Uiso 1 1 calc R . . H18C H 0.0118 0.4860 0.2246 0.030 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 0.0249(6) 0.0238(6) 0.0251(6) -0.0035(5) -0.0058(5) -0.0035(5) N1 0.0173(6) 0.0151(6) 0.0126(6) 0.0006(5) 0.0014(5) -0.0004(5) C1 0.0193(8) 0.0108(7) 0.0176(7) 0.0058(5) 0.0027(6) 0.0023(6) C2 0.0220(8) 0.0133(7) 0.0165(7) 0.0023(6) 0.0033(6) 0.0021(6) C3 0.0284(9) 0.0165(8) 0.0181(8) 0.0034(6) 0.0077(7) 0.0054(6) C4 0.0211(8) 0.0179(8) 0.0289(9) 0.0069(6) 0.0096(7) 0.0057(6) C5 0.0200(8) 0.0153(8) 0.0224(8) 0.0041(6) -0.0001(6) 0.0008(6) C6 0.0221(8) 0.0097(7) 0.0159(7) 0.0038(5) 0.0020(6) 0.0021(6) C7 0.0188(7) 0.0113(7) 0.0158(7) 0.0028(5) -0.0006(6) 0.0003(6) C8 0.0234(8) 0.0108(7) 0.0181(8) 0.0034(6) -0.0015(6) 0.0008(6) C9 0.0270(8) 0.0104(7) 0.0156(7) 0.0049(5) 0.0020(6) 0.0028(6) C10 0.0265(8) 0.0100(7) 0.0131(7) 0.0040(5) 0.0035(6) 0.0030(6) C11 0.0200(8) 0.0099(7) 0.0129(7) 0.0037(5) 0.0001(6) 0.0008(5) C12 0.0344(9) 0.0132(8) 0.0171(8) 0.0016(6) 0.0012(7) 0.0029(6) C13 0.0415(10) 0.0174(8) 0.0162(8) 0.0023(6) 0.0099(7) 0.0067(7) C14 0.0300(9) 0.0173(8) 0.0246(8) 0.0052(6) 0.0124(7) 0.0064(7) C15 0.0248(8) 0.0159(8) 0.0184(8) 0.0027(6) 0.0038(6) 0.0017(6) C16 0.0165(8) 0.0173(8) 0.0163(8) 0.0005(6) 0.0007(6) -0.0050(6) C17 0.0146(7) 0.0177(8) 0.0188(8) 0.0020(6) 0.0026(6) 0.0010(6) C18 0.0245(8) 0.0264(9) 0.0187(8) 0.0003(6) 0.0051(7) -0.0032(7) O1A 0.0211(6) 0.0235(6) 0.0241(6) 0.0039(5) -0.0027(5) 0.0024(5) N1A 0.0168(6) 0.0157(6) 0.0122(6) 0.0002(5) 0.0032(5) -0.0011(5) C1A 0.0282(8) 0.0092(7) 0.0121(7) -0.0031(5) 0.0049(6) -0.0050(6) C2A 0.0266(8) 0.0148(7) 0.0171(8) -0.0014(6) 0.0054(6) -0.0021(6) C3A 0.0284(9) 0.0180(8) 0.0201(8) -0.0022(6) 0.0117(7) -0.0035(6) C4A 0.0370(9) 0.0157(8) 0.0141(8) -0.0022(6) 0.0095(7) -0.0047(7) C5A 0.0301(9) 0.0139(8) 0.0156(8) -0.0012(6) 0.0033(7) -0.0022(6) C6A 0.0259(8) 0.0110(7) 0.0155(7) -0.0049(5) 0.0035(6) -0.0034(6) C7A 0.0236(8) 0.0116(7) 0.0152(7) -0.0021(5) 0.0001(6) -0.0023(6) C8A 0.0201(7) 0.0119(7) 0.0143(7) -0.0023(5) 0.0004(6) -0.0017(6) C9A 0.0196(7) 0.0100(7) 0.0135(7) -0.0033(5) 0.0007(6) -0.0016(5) C10A 0.0219(8) 0.0103(7) 0.0135(7) -0.0033(5) 0.0041(6) -0.0034(6) C11A 0.0190(8) 0.0134(7) 0.0199(8) -0.0014(6) 0.0015(6) 0.0011(6) C12A 0.0188(8) 0.0168(8) 0.0240(8) -0.0032(6) 0.0093(6) -0.0029(6) C13A 0.0243(8) 0.0151(8) 0.0154(7) -0.0022(6) 0.0076(6) -0.0037(6) C14A 0.0198(8) 0.0128(7) 0.0154(7) -0.0024(5) 0.0031(6) -0.0025(6) C15A 0.0178(7) 0.0118(7) 0.0161(7) -0.0058(5) 0.0050(6) -0.0028(6) C16A 0.0144(7) 0.0169(8) 0.0158(7) -0.0002(6) 0.0006(6) 0.0027(6) C17A 0.0135(7) 0.0189(8) 0.0204(8) -0.0018(6) 0.0029(6) -0.0007(6) C18A 0.0252(9) 0.0258(9) 0.0213(8) 0.0010(6) 0.0043(7) 0.0021(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 O1 C8 1.2298(18) . ? N1 C11 1.3522(18) . ? N1 C1 1.4098(18) . ? N1 C16 1.4631(18) . ? C1 C2 1.387(2) . ? C1 C6 1.418(2) . ? C2 C3 1.384(2) . ? C3 C4 1.401(2) . ? C4 C5 1.382(2) . ? C5 C6 1.399(2) . ? C6 C7 1.438(2) . ? C7 C11 1.373(2) . ? C7 C8 1.448(2) . ? C8 C9 1.516(2) . ? C9 C12 1.371(2) . ? C9 C10 1.417(2) . ? C10 C15 1.379(2) . ? C10 C11 1.479(2) . ? C12 C13 1.398(2) . ? C13 C14 1.381(2) . ? C14 C15 1.405(2) . ? C16 C17 1.4922(19) . ? C17 C18 1.319(2) . ? O1A C7A 1.2315(18) . ? N1A C9A 1.3510(17) . ? N1A C15A 1.4127(18) . ? N1A C16A 1.4619(18) . ? C1A C2A 1.382(2) . ? C1A C6A 1.419(2) . ? C1A C9A 1.4788(19) . ? C2A C3A 1.405(2) . ? C3A C4A 1.380(2) . ? C4A C5A 1.398(2) . ? C5A C6A 1.367(2) . ? C6A C7A 1.514(2) . ? C7A C8A 1.447(2) . ? C8A C9A 1.375(2) . ? C8A C10A 1.438(2) . ? C10A C11A 1.399(2) . ? C10A C15A 1.413(2) . ? C11A C12A 1.384(2) . ? C12A C13A 1.402(2) . ? C13A C14A 1.383(2) . ? C14A C15A 1.387(2) . ? C16A C17A 1.4976(19) . ? C17A C18A 1.314(2) . ? 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 N1 C1 107.43(12) . . ? C11 N1 C16 127.49(12) . . ? C1 N1 C16 125.06(12) . . ? C2 C1 N1 129.02(13) . . ? C2 C1 C6 122.43(14) . . ? N1 C1 C6 108.55(12) . . ? C3 C2 C1 117.27(14) . . ? C2 C3 C4 121.45(14) . . ? C5 C4 C3 121.08(14) . . ? C4 C5 C6 118.92(14) . . ? C5 C6 C1 118.84(13) . . ? C5 C6 C7 135.78(14) . . ? C1 C6 C7 105.38(13) . . ? C11 C7 C6 107.47(13) . . ? C11 C7 C8 109.24(14) . . ? C6 C7 C8 143.28(14) . . ? O1 C8 C7 129.60(14) . . ? O1 C8 C9 125.67(14) . . ? C7 C8 C9 104.72(12) . . ? C12 C9 C10 121.27(15) . . ? C12 C9 C8 129.03(14) . . ? C10 C9 C8 109.70(13) . . ? C15 C10 C9 120.13(14) . . ? C15 C10 C11 135.27(14) . . ? C9 C10 C11 104.60(13) . . ? N1 C11 C7 111.17(13) . . ? N1 C11 C10 137.08(13) . . ? C7 C11 C10 111.74(13) . . ? C9 C12 C13 118.53(15) . . ? C14 C13 C12 120.61(14) . . ? C13 C14 C15 121.20(15) . . ? C10 C15 C14 118.26(14) . . ? N1 C16 C17 113.20(12) . . ? C18 C17 C16 122.36(14) . . ? C9A N1A C15A 107.12(11) . . ? C9A N1A C16A 127.70(12) . . ? C15A N1A C16A 125.15(12) . . ? C2A C1A C6A 120.13(13) . . ? C2A C1A C9A 135.19(14) . . ? C6A C1A C9A 104.68(13) . . ? C1A C2A C3A 118.17(14) . . ? C4A C3A C2A 121.20(15) . . ? C3A C4A C5A 120.67(14) . . ? C6A C5A C4A 118.62(14) . . ? C5A C6A C1A 121.21(14) . . ? C5A C6A C7A 129.08(14) . . ? C1A C6A C7A 109.71(12) . . ? O1A C7A C8A 129.74(14) . . ? O1A C7A C6A 125.62(13) . . ? C8A C7A C6A 104.63(12) . . ? C9A C8A C10A 107.43(13) . . ? C9A C8A C7A 109.47(13) . . ? C10A C8A C7A 143.08(14) . . ? N1A C9A C8A 111.28(13) . . ? N1A C9A C1A 137.22(14) . . ? C8A C9A C1A 111.50(13) . . ? C11A C10A C15A 119.07(13) . . ? C11A C10A C8A 135.60(13) . . ? C15A C10A C8A 105.33(12) . . ? C12A C11A C10A 118.69(14) . . ? C11A C12A C13A 121.03(14) . . ? C14A C13A C12A 121.54(14) . . ? C13A C14A C15A 117.17(14) . . ? C14A C15A N1A 128.66(13) . . ? C14A C15A C10A 122.50(13) . . ? N1A C15A C10A 108.84(12) . . ? N1A C16A C17A 112.56(12) . . ? C18A C17A C16A 122.55(14) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.462 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.056 data_baracb _database_code_depnum_ccdc_archive 'CCDC 923057' #TrackingRef 'web_deposit_cif_file_3_Louis-PhilippeBonhomme-Beaulieu_1359991019.Compound 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 N2 O3' _chemical_formula_weight 408.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.4793(18) _cell_length_b 20.849(7) _cell_length_c 17.361(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.866(18) _cell_angle_gamma 90.00 _cell_volume 1959.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9643 _exptl_absorpt_correction_T_max 0.9995 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38280 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.3444 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3457 _reflns_number_gt 1520 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction 'SAINT (Bruker, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ATOMS V.5.0' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0000P)^2^+0.0003P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0186(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3457 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2642 _refine_ls_R_factor_gt 0.1245 _refine_ls_wR_factor_ref 0.3401 _refine_ls_wR_factor_gt 0.2698 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.9450(7) 0.26838(12) 0.56499(16) 0.0794(13) Uani 1 1 d . . . O2 O 0.7177(7) 0.04379(11) 0.32821(14) 0.0493(9) Uani 1 1 d . . . O3 O 0.7508(8) -0.12351(14) -0.12241(17) 0.0685(11) Uani 1 1 d . . . H3 H 0.8540 -0.1513 -0.1037 0.082 Uiso 1 1 calc R . . N1 N 0.6483(12) 0.1957(2) 0.4950(3) 0.105(2) Uani 1 1 d . . . N2 N 0.7698(8) 0.02090(13) 0.25333(19) 0.0478(11) Uani 1 1 d . . . C1 C 0.1475(10) 0.0884(2) 0.5014(2) 0.0544(14) Uani 1 1 d . . . H1 H 0.0539 0.0627 0.4624 0.065 Uiso 1 1 calc R . . C2 C 0.0976(9) 0.08879(19) 0.5789(2) 0.0524(13) Uani 1 1 d . . . H2 H -0.0286 0.0618 0.5926 0.063 Uiso 1 1 calc R . . C3 C 0.2269(9) 0.12716(19) 0.6345(2) 0.0430(12) Uani 1 1 d . . . H3A H 0.1834 0.1282 0.6854 0.052 Uiso 1 1 calc R . . C4 C 0.4218(10) 0.16485(19) 0.6177(3) 0.0559(14) Uani 1 1 d . . . H4 H 0.5169 0.1907 0.6563 0.067 Uiso 1 1 calc R . . C5 C 0.4705(9) 0.16257(19) 0.5399(3) 0.0475(13) Uani 1 1 d . . . C6 C 0.3258(10) 0.1245(2) 0.4855(2) 0.0497(14) Uani 1 1 d . . . C7 C 0.4102(8) 0.13106(17) 0.4063(2) 0.0336(11) Uani 1 1 d . . . C8 C 0.5881(10) 0.1719(2) 0.4173(3) 0.0484(13) Uani 1 1 d . . . C9 C 0.8562(12) 0.2373(2) 0.5045(3) 0.0770(19) Uani 1 1 d . . . C10 C 0.9208(10) 0.24136(19) 0.4179(2) 0.0419(12) Uani 1 1 d . . . C11 C 1.0981(9) 0.27612(17) 0.3959(2) 0.0394(12) Uani 1 1 d . . . H11 H 1.2014 0.3019 0.4325 0.047 Uiso 1 1 calc R . . C12 C 1.1327(9) 0.27444(17) 0.3158(2) 0.0547(15) Uani 1 1 d . . . H12 H 1.2610 0.2989 0.2990 0.066 Uiso 1 1 calc R . . C13 C 0.9782(9) 0.23701(18) 0.2629(2) 0.0477(13) Uani 1 1 d . . . H13 H 1.0002 0.2369 0.2097 0.057 Uiso 1 1 calc R . . C14 C 0.7938(10) 0.20000(18) 0.2859(3) 0.0576(15) Uani 1 1 d . . . H14 H 0.6905 0.1739 0.2497 0.069 Uiso 1 1 calc R . . C15 C 0.7636(10) 0.20236(19) 0.3657(3) 0.0574(14) Uani 1 1 d . . . C16 C 0.3247(10) 0.09523(16) 0.3360(2) 0.0619(16) Uani 1 1 d . . . H16B H 0.3522 0.1206 0.2899 0.074 Uiso 1 1 calc R . . H16A H 0.1453 0.0870 0.3321 0.074 Uiso 1 1 calc R . . C17 C 0.4639(9) 0.03119(19) 0.3368(2) 0.0486(13) Uani 1 1 d . . . H17 H 0.4566 0.0078 0.3867 0.058 Uiso 1 1 calc R . . C18 C 0.3675(8) -0.01159(17) 0.2672(2) 0.0408(12) Uani 1 1 d . . . H18B H 0.3364 -0.0558 0.2840 0.049 Uiso 1 1 calc R . . H18A H 0.2138 0.0060 0.2371 0.049 Uiso 1 1 calc R . . C19 C 0.5760(9) -0.00982(16) 0.2204(2) 0.0371(12) Uani 1 1 d . . . C20 C 0.5739(8) -0.03918(17) 0.1418(2) 0.0356(12) Uani 1 1 d . . . C21 C 0.7582(8) -0.02871(16) 0.0960(2) 0.0346(11) Uani 1 1 d . . . H21 H 0.8928 -0.0014 0.1151 0.041 Uiso 1 1 calc R . . C22 C 0.7502(9) -0.05704(15) 0.0235(2) 0.0408(13) Uani 1 1 d . . . H22 H 0.8763 -0.0483 -0.0069 0.049 Uiso 1 1 calc R . . C23 C 0.5575(10) -0.09828(17) -0.0048(2) 0.0399(12) Uani 1 1 d . . . C24 C 0.3732(9) -0.10979(16) 0.0398(2) 0.0441(13) Uani 1 1 d . . . H24 H 0.2396 -0.1373 0.0205 0.053 Uiso 1 1 calc R . . C25 C 0.3821(8) -0.08089(15) 0.1139(2) 0.0378(12) Uani 1 1 d . . . H25 H 0.2571 -0.0899 0.1447 0.045 Uiso 1 1 calc R . . C26 C 0.5354(11) -0.1292(2) -0.0876(2) 0.0594(15) Uani 1 1 d . . . H26B H 0.4954 -0.1753 -0.0836 0.071 Uiso 1 1 calc R . . H26A H 0.3964 -0.1087 -0.1221 0.071 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 0.111(3) 0.0397(16) 0.0641(19) -0.0071(15) -0.061(2) -0.0054(19) O2 0.066(3) 0.0445(16) 0.0317(17) -0.0116(13) -0.0119(16) 0.0034(18) O3 0.092(3) 0.063(2) 0.0517(19) -0.0002(15) 0.016(2) 0.027(2) N1 0.107(6) 0.068(3) 0.128(5) -0.018(3) -0.026(4) 0.038(4) N2 0.059(3) 0.0326(18) 0.047(2) 0.0020(17) -0.009(2) -0.001(2) C1 0.052(4) 0.058(3) 0.054(3) 0.000(2) 0.011(3) 0.008(3) C2 0.058(4) 0.053(3) 0.047(3) 0.010(2) 0.012(3) 0.019(3) C3 0.051(4) 0.048(3) 0.029(2) 0.003(2) 0.004(3) 0.010(3) C4 0.059(4) 0.044(3) 0.059(3) 0.016(2) -0.006(3) 0.004(3) C5 0.048(4) 0.040(3) 0.063(3) 0.031(2) 0.034(3) -0.001(2) C6 0.053(4) 0.044(3) 0.048(3) 0.009(2) -0.008(3) 0.003(3) C7 0.034(3) 0.026(2) 0.039(3) -0.0140(19) 0.000(2) 0.002(2) C8 0.049(4) 0.035(2) 0.055(3) -0.002(2) -0.011(3) 0.012(3) C9 0.078(5) 0.022(3) 0.120(5) 0.016(3) -0.019(4) 0.019(3) C10 0.053(4) 0.035(2) 0.039(3) 0.004(2) 0.012(3) 0.000(3) C11 0.045(4) 0.030(2) 0.042(3) 0.0052(19) 0.004(2) 0.006(2) C12 0.080(5) 0.033(2) 0.048(3) 0.004(2) 0.000(3) 0.004(2) C13 0.053(4) 0.047(3) 0.041(3) -0.010(2) 0.001(2) 0.004(3) C14 0.062(4) 0.036(2) 0.069(4) -0.002(2) -0.010(3) -0.007(3) C15 0.055(4) 0.037(3) 0.081(4) 0.029(3) 0.015(3) 0.019(3) C16 0.072(4) 0.048(3) 0.054(3) -0.029(2) -0.027(3) 0.010(3) C17 0.035(4) 0.057(3) 0.048(3) -0.001(2) -0.009(3) 0.012(3) C18 0.038(4) 0.037(2) 0.043(2) -0.0134(19) -0.006(2) -0.003(2) C19 0.042(4) 0.028(2) 0.040(3) 0.003(2) 0.001(3) 0.000(2) C20 0.040(4) 0.027(2) 0.038(3) 0.0029(19) 0.001(2) 0.008(2) C21 0.034(3) 0.031(2) 0.037(3) -0.001(2) -0.002(2) -0.003(2) C22 0.047(4) 0.026(2) 0.047(3) 0.006(2) 0.000(2) 0.008(2) C23 0.054(4) 0.025(2) 0.038(3) 0.0026(19) -0.003(3) 0.001(2) C24 0.067(4) 0.029(2) 0.031(2) -0.001(2) -0.008(3) -0.011(2) C25 0.047(4) 0.029(2) 0.035(2) 0.0079(19) 0.000(2) 0.003(2) C26 0.082(5) 0.056(3) 0.042(3) -0.012(2) 0.016(3) -0.008(3) _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 C9 1.265(5) . ? O2 C17 1.445(5) . ? O2 N2 1.454(4) . ? O3 C26 1.411(5) . ? N1 C9 1.422(7) . ? N1 C8 1.426(5) . ? N1 C5 1.506(7) . ? N2 C19 1.295(5) . ? C1 C6 1.296(6) . ? C1 C2 1.414(5) . ? C2 C3 1.365(5) . ? C3 C4 1.393(6) . ? C4 C5 1.417(6) . ? C5 C6 1.386(6) . ? C6 C7 1.523(6) . ? C7 C8 1.287(6) . ? C7 C16 1.446(5) . ? C8 C15 1.548(7) . ? C9 C10 1.599(7) . ? C10 C11 1.315(6) . ? C10 C15 1.409(6) . ? C11 C12 1.432(5) . ? C12 C13 1.389(5) . ? C13 C14 1.379(6) . ? C14 C15 1.421(6) . ? C16 C17 1.537(5) . ? C17 C18 1.530(5) . ? C18 C19 1.500(5) . ? C19 C20 1.493(5) . ? C20 C25 1.392(5) . ? C20 C21 1.396(5) . ? C21 C22 1.385(5) . ? C22 C23 1.391(5) . ? C23 C24 1.385(6) . ? C23 C26 1.564(5) . ? C24 C25 1.414(5) . ? 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 C17 O2 N2 111.0(3) . . ? C9 N1 C8 112.7(6) . . ? C9 N1 C5 142.2(5) . . ? C8 N1 C5 104.9(4) . . ? C19 N2 O2 107.2(4) . . ? C6 C1 C2 117.5(4) . . ? C3 C2 C1 121.4(5) . . ? C2 C3 C4 120.9(4) . . ? C3 C4 C5 116.4(4) . . ? C6 C5 C4 119.8(4) . . ? C6 C5 N1 104.9(4) . . ? C4 C5 N1 135.3(5) . . ? C1 C6 C5 123.9(4) . . ? C1 C6 C7 126.0(4) . . ? C5 C6 C7 110.0(4) . . ? C8 C7 C16 127.4(4) . . ? C8 C7 C6 104.7(4) . . ? C16 C7 C6 127.7(4) . . ? C7 C8 N1 115.5(5) . . ? C7 C8 C15 135.2(4) . . ? N1 C8 C15 109.4(5) . . ? O1 C9 N1 127.4(6) . . ? O1 C9 C10 129.8(5) . . ? N1 C9 C10 102.3(5) . . ? C11 C10 C15 122.5(4) . . ? C11 C10 C9 125.7(4) . . ? C15 C10 C9 111.9(5) . . ? C10 C11 C12 118.9(4) . . ? C13 C12 C11 119.8(5) . . ? C14 C13 C12 121.5(4) . . ? C13 C14 C15 117.6(4) . . ? C10 C15 C14 119.7(5) . . ? C10 C15 C8 103.7(4) . . ? C14 C15 C8 136.6(5) . . ? C7 C16 C17 110.2(3) . . ? O2 C17 C18 104.1(4) . . ? O2 C17 C16 109.0(4) . . ? C18 C17 C16 112.9(3) . . ? C19 C18 C17 102.4(4) . . ? N2 C19 C20 119.8(4) . . ? N2 C19 C18 114.4(3) . . ? C20 C19 C18 125.8(4) . . ? C25 C20 C21 118.2(3) . . ? C25 C20 C19 118.2(4) . . ? C21 C20 C19 123.5(4) . . ? C22 C21 C20 121.8(4) . . ? C21 C22 C23 120.0(4) . . ? C24 C23 C22 119.3(4) . . ? C24 C23 C26 118.9(4) . . ? C22 C23 C26 121.8(4) . . ? C23 C24 C25 120.6(4) . . ? C20 C25 C24 120.1(4) . . ? O3 C26 C23 114.0(4) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.686 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.093 data_mc1a_0m _database_code_depnum_ccdc_archive 'CCDC 923165' #TrackingRef 'web_deposit_cif_file_0_Louis-PhilippeBonhomme-Beaulieu_1359991019.Compound 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N2 O2' _chemical_formula_weight 318.36 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 P21/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 7.7470(5) _cell_length_b 26.1530(19) _cell_length_c 8.5985(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.664(3) _cell_angle_gamma 90.00 _cell_volume 1650.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 7824 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 26.37 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9673 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _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 Kappa APEX II CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27855 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 26.49 _reflns_number_total 3371 _reflns_number_gt 2521 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2 _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _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^)+(0.0458P)^2^+0.5763P] 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 3371 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 -0.03022(15) 0.09656(4) 1.10497(13) 0.0239(3) Uani 1 1 d . . . O2 O 0.61572(15) 0.24184(4) 1.02722(13) 0.0228(3) Uani 1 1 d . . . N1 N -0.00310(17) 0.11346(5) 0.85569(15) 0.0175(3) Uani 1 1 d . . . N2 N 0.36368(17) 0.21583(5) 0.82305(15) 0.0162(3) Uani 1 1 d . . . H2 H 0.2825 0.2256 0.7304 0.019 Uiso 1 1 calc R . . C1 C 0.0603(2) 0.09461(6) 1.01079(18) 0.0162(3) Uani 1 1 d . . . C2 C 0.2442(2) 0.06955(6) 1.06706(17) 0.0154(3) Uani 1 1 d . . . C3 C 0.2509(2) 0.01947(6) 1.12422(18) 0.0196(4) Uani 1 1 d . . . H3 H 0.1407 0.0016 1.1127 0.023 Uiso 1 1 calc R . . C4 C 0.4158(2) -0.00454(6) 1.19745(19) 0.0241(4) Uani 1 1 d . . . H4 H 0.4191 -0.0391 1.2319 0.029 Uiso 1 1 calc R . . C5 C 0.5768(2) 0.02232(6) 1.2203(2) 0.0244(4) Uani 1 1 d . . . H5 H 0.6906 0.0062 1.2724 0.029 Uiso 1 1 calc R . . C6 C 0.5720(2) 0.07228(6) 1.16764(19) 0.0216(4) Uani 1 1 d . . . H6 H 0.6830 0.0904 1.1862 0.026 Uiso 1 1 calc R . . C7 C 0.4063(2) 0.09674(6) 1.08717(17) 0.0166(3) Uani 1 1 d . . . C8 C 0.4123(2) 0.15019(6) 1.03316(18) 0.0170(3) Uani 1 1 d . . . H8 H 0.4708 0.1748 1.1141 0.020 Uiso 1 1 calc R . . C9 C 0.3410(2) 0.16613(6) 0.87857(18) 0.0149(3) Uani 1 1 d . . . C10 C 0.2445(2) 0.13131(6) 0.74189(17) 0.0140(3) Uani 1 1 d . . . C11 C 0.3184(2) 0.12372(6) 0.61429(18) 0.0167(3) Uani 1 1 d . . . H11 H 0.4258 0.1416 0.6164 0.020 Uiso 1 1 calc R . . C12 C 0.2386(2) 0.09103(6) 0.48653(19) 0.0194(4) Uani 1 1 d . . . H12 H 0.2922 0.0859 0.4026 0.023 Uiso 1 1 calc R . . C13 C 0.0792(2) 0.06556(6) 0.48045(19) 0.0206(4) Uani 1 1 d . . . H13 H 0.0221 0.0434 0.3913 0.025 Uiso 1 1 calc R . . C14 C 0.0041(2) 0.07253(6) 0.60447(18) 0.0189(4) Uani 1 1 d . . . H14 H -0.1045 0.0549 0.6005 0.023 Uiso 1 1 calc R . . C15 C 0.0859(2) 0.10506(6) 0.73494(17) 0.0148(3) Uani 1 1 d . . . C16 C -0.1843(2) 0.13769(6) 0.7984(2) 0.0226(4) Uani 1 1 d . . . H16A H -0.2413 0.1352 0.8860 0.027 Uiso 1 1 calc R . . H16B H -0.2623 0.1188 0.7016 0.027 Uiso 1 1 calc R . . C17 C -0.1762(2) 0.19233(7) 0.7534(2) 0.0310(4) Uani 1 1 d . . . H17 H -0.1033 0.2149 0.8346 0.037 Uiso 1 1 calc R . . C18 C -0.2636(3) 0.21129(8) 0.6084(3) 0.0426(5) Uani 1 1 d . . . H18A H -0.3376 0.1897 0.5245 0.051 Uiso 1 1 calc R . . H18B H -0.2529 0.2466 0.5872 0.051 Uiso 1 1 calc R . . C19 C 0.4959(2) 0.25026(6) 0.89592(18) 0.0184(3) Uani 1 1 d . . . C20 C 0.4863(2) 0.29975(6) 0.8061(2) 0.0271(4) Uani 1 1 d . . . H20A H 0.4557 0.3275 0.8694 0.041 Uiso 1 1 calc R . . H20B H 0.3924 0.2974 0.6983 0.041 Uiso 1 1 calc R . . H20C H 0.6045 0.3068 0.7917 0.041 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 0.0200(6) 0.0347(7) 0.0205(6) 0.0025(5) 0.0113(5) 0.0024(5) O2 0.0194(6) 0.0247(6) 0.0188(6) 0.0005(5) -0.0018(5) -0.0037(5) N1 0.0123(7) 0.0249(7) 0.0165(7) 0.0032(5) 0.0064(5) 0.0022(5) N2 0.0143(7) 0.0171(7) 0.0145(6) 0.0010(5) 0.0008(5) -0.0001(5) C1 0.0169(8) 0.0148(8) 0.0173(8) -0.0024(6) 0.0061(6) -0.0036(6) C2 0.0162(8) 0.0204(8) 0.0097(7) -0.0018(6) 0.0041(6) -0.0006(6) C3 0.0211(9) 0.0206(8) 0.0170(8) -0.0006(6) 0.0060(6) -0.0038(7) C4 0.0288(10) 0.0190(8) 0.0227(9) 0.0045(7) 0.0057(7) 0.0028(7) C5 0.0194(9) 0.0284(9) 0.0236(9) 0.0067(7) 0.0045(7) 0.0073(7) C6 0.0151(8) 0.0297(9) 0.0195(8) 0.0038(7) 0.0048(6) -0.0014(7) C7 0.0177(8) 0.0211(8) 0.0110(7) -0.0005(6) 0.0048(6) 0.0003(7) C8 0.0152(8) 0.0194(8) 0.0161(8) -0.0030(6) 0.0044(6) -0.0027(6) C9 0.0115(8) 0.0168(8) 0.0169(8) -0.0008(6) 0.0054(6) -0.0002(6) C10 0.0134(8) 0.0144(8) 0.0135(7) 0.0018(6) 0.0032(6) 0.0028(6) C11 0.0140(8) 0.0203(8) 0.0162(8) 0.0031(6) 0.0052(6) 0.0019(6) C12 0.0238(9) 0.0200(8) 0.0146(8) 0.0017(6) 0.0063(6) 0.0056(7) C13 0.0273(9) 0.0153(8) 0.0158(8) -0.0004(6) 0.0020(7) -0.0004(7) C14 0.0177(8) 0.0178(8) 0.0184(8) 0.0025(6) 0.0021(6) -0.0026(6) C15 0.0140(8) 0.0178(8) 0.0121(7) 0.0043(6) 0.0034(6) 0.0033(6) C16 0.0127(8) 0.0321(10) 0.0242(9) 0.0067(7) 0.0076(7) 0.0039(7) C17 0.0198(9) 0.0285(10) 0.0477(12) 0.0014(8) 0.0148(8) 0.0053(8) C18 0.0323(11) 0.0433(12) 0.0616(14) 0.0262(10) 0.0281(10) 0.0113(9) C19 0.0164(8) 0.0202(8) 0.0176(8) -0.0024(6) 0.0042(7) -0.0004(6) C20 0.0270(10) 0.0218(9) 0.0257(9) 0.0019(7) -0.0007(7) -0.0064(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 O1 C1 1.2303(19) . ? O2 C19 1.2305(18) . ? N1 C1 1.3578(19) . ? N1 C15 1.4353(19) . ? N1 C16 1.4736(19) . ? N2 C19 1.357(2) . ? N2 C9 1.415(2) . ? C1 C2 1.501(2) . ? C2 C3 1.394(2) . ? C2 C7 1.405(2) . ? C3 C4 1.381(2) . ? C4 C5 1.389(2) . ? C5 C6 1.379(2) . ? C6 C7 1.403(2) . ? C7 C8 1.478(2) . ? C8 C9 1.333(2) . ? C9 C10 1.486(2) . ? C10 C15 1.392(2) . ? C10 C11 1.404(2) . ? C11 C12 1.373(2) . ? C12 C13 1.389(2) . ? C13 C14 1.381(2) . ? C14 C15 1.389(2) . ? C16 C17 1.487(2) . ? C17 C18 1.311(3) . ? C19 C20 1.497(2) . ? 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 C15 123.25(12) . . ? C1 N1 C16 119.41(13) . . ? C15 N1 C16 116.78(12) . . ? C19 N2 C9 127.64(12) . . ? O1 C1 N1 121.88(14) . . ? O1 C1 C2 119.21(13) . . ? N1 C1 C2 118.89(13) . . ? C3 C2 C7 120.06(14) . . ? C3 C2 C1 116.67(14) . . ? C7 C2 C1 122.52(13) . . ? C4 C3 C2 120.85(15) . . ? C3 C4 C5 119.47(15) . . ? C6 C5 C4 120.25(15) . . ? C5 C6 C7 121.21(15) . . ? C6 C7 C2 118.08(14) . . ? C6 C7 C8 118.07(14) . . ? C2 C7 C8 123.81(14) . . ? C9 C8 C7 124.37(14) . . ? C8 C9 N2 124.57(13) . . ? C8 C9 C10 122.70(14) . . ? N2 C9 C10 112.44(12) . . ? C15 C10 C11 118.13(13) . . ? C15 C10 C9 123.37(13) . . ? C11 C10 C9 118.49(13) . . ? C12 C11 C10 121.43(15) . . ? C11 C12 C13 119.73(15) . . ? C14 C13 C12 119.79(14) . . ? C13 C14 C15 120.56(15) . . ? C14 C15 C10 120.35(14) . . ? C14 C15 N1 118.51(14) . . ? C10 C15 N1 121.02(13) . . ? N1 C16 C17 112.67(14) . . ? C18 C17 C16 124.01(19) . . ? O2 C19 N2 122.77(14) . . ? O2 C19 C20 121.77(14) . . ? N2 C19 C20 115.47(13) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.230 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.051 data_mc2_0m _database_code_depnum_ccdc_archive 'CCDC 923166' #TrackingRef 'web_deposit_cif_file_1_Louis-PhilippeBonhomme-Beaulieu_1359991019.Compound 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 N O' _chemical_formula_sum 'C18 H13 N O' _chemical_formula_weight 259.29 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 'P 21/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 17.1588(13) _cell_length_b 7.6525(7) _cell_length_c 20.1851(16) _cell_angle_alpha 90.00 _cell_angle_beta 107.382(3) _cell_angle_gamma 90.00 _cell_volume 2529.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9942 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 28.26 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9590 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX II CCD' _diffrn_measurement_method ' \f & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 59114 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 24.71 _reflns_number_total 4276 _reflns_number_gt 3305 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2 _computing_cell_refinement 'SAINT (Bruker 2001)' _computing_data_reduction 'SAINT (Bruker 2001)' _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^)+(0.0602P)^2^+0.3815P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4276 _refine_ls_number_parameters 465 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.40257(5) 0.76674(11) 1.09674(4) 0.0241(2) Uani 1 1 d . . . O2 O 0.89706(5) 0.48509(12) 0.60417(4) 0.0281(2) Uani 1 1 d . . . C29 C 0.68854(7) 0.71917(15) 0.42937(6) 0.0159(3) Uani 1 1 d . . . C9 C 0.18446(7) 0.53117(15) 0.93089(6) 0.0157(3) Uani 1 1 d . . . C34 C 0.90690(8) 0.66116(16) 0.45390(7) 0.0223(3) Uani 1 1 d . . . C3 C 0.25800(8) 0.82561(17) 1.16097(6) 0.0223(3) Uani 1 1 d . . . C7 C 0.18903(7) 0.68353(15) 1.05114(6) 0.0179(3) Uani 1 1 d . . . C2 C 0.26000(7) 0.75199(16) 1.09910(6) 0.0185(3) Uani 1 1 d . . . C30 C 0.76163(7) 0.73721(15) 0.40679(6) 0.0168(3) Uani 1 1 d . . . C35 C 0.82813(7) 0.66501(15) 0.45899(6) 0.0176(3) Uani 1 1 d . . . N2 N 0.79672(6) 0.60443(13) 0.51111(5) 0.0171(2) Uani 1 1 d . . . C5 C 0.11321(8) 0.76424(16) 1.12817(6) 0.0230(3) Uani 1 1 d . . . C31 C 0.77527(8) 0.80617(16) 0.34738(6) 0.0200(3) Uani 1 1 d . . . C32 C 0.85365(8) 0.80101(17) 0.34124(7) 0.0242(3) Uani 1 1 d . . . C4 C 0.18350(8) 0.83098(17) 1.17523(7) 0.0232(3) Uani 1 1 d . . . C6 C 0.11478(8) 0.68967(16) 1.06577(6) 0.0201(3) Uani 1 1 d . . . N1 N 0.29714(6) 0.64487(13) 1.00799(5) 0.0167(2) Uani 1 1 d . . . C36 C 0.60415(7) 0.78078(18) 0.39109(6) 0.0194(3) Uani 1 1 d . . . C37 C 0.56751(7) 0.69187(17) 0.32254(6) 0.0189(3) Uani 1 1 d . . . C1 C 0.33073(7) 0.72808(15) 1.07164(6) 0.0178(3) Uani 1 1 d . . . C17 C 0.06482(7) 0.55444(17) 0.82401(6) 0.0189(3) Uani 1 1 d . . . C14 C 0.40142(7) 0.57483(16) 0.94563(6) 0.0200(3) Uani 1 1 d . . . C10 C 0.25481(7) 0.50756(15) 0.90492(6) 0.0162(3) Uani 1 1 d . . . C8 C 0.21301(7) 0.61451(15) 0.99279(6) 0.0161(3) Uani 1 1 d . . . C15 C 0.32429(7) 0.57875(15) 0.95412(6) 0.0168(3) Uani 1 1 d . . . C16 C 0.09858(7) 0.47427(17) 0.89483(6) 0.0185(3) Uani 1 1 d . . . C21 C 0.82597(7) 0.52382(16) 0.57560(6) 0.0204(3) Uani 1 1 d . . . C22 C 0.75219(7) 0.50365(16) 0.59932(6) 0.0205(3) Uani 1 1 d . . . C28 C 0.71272(7) 0.63755(15) 0.49204(6) 0.0164(3) Uani 1 1 d . . . C26 C 0.60754(8) 0.56989(16) 0.55917(6) 0.0220(3) Uani 1 1 d . . . C27 C 0.68374(7) 0.57242(15) 0.54839(6) 0.0181(3) Uani 1 1 d . . . C13 C 0.40835(8) 0.49787(17) 0.88524(6) 0.0217(3) Uani 1 1 d . . . C11 C 0.26348(7) 0.43149(16) 0.84487(6) 0.0176(3) Uani 1 1 d . . . C38 C 0.53426(8) 0.7755(2) 0.26398(7) 0.0281(3) Uani 1 1 d . . . C12 C 0.34036(7) 0.42821(17) 0.83544(6) 0.0195(3) Uani 1 1 d . . . C18 C 0.03373(8) 0.4642(2) 0.76676(7) 0.0274(3) Uani 1 1 d . . . C23 C 0.74580(9) 0.43339(17) 0.66060(7) 0.0275(3) Uani 1 1 d . . . C25 C 0.60162(9) 0.50019(18) 0.62114(7) 0.0280(3) Uani 1 1 d . . . C24 C 0.66928(9) 0.43270(18) 0.67104(7) 0.0300(3) Uani 1 1 d . . . C33 C 0.91848(8) 0.72921(17) 0.39388(7) 0.0256(3) Uani 1 1 d . . . H16A H 0.0632(7) 0.5015(16) 0.9234(6) 0.014(3) Uiso 1 1 d . . . H17 H 0.0679(8) 0.6840(19) 0.8224(6) 0.026(3) Uiso 1 1 d . . . H32 H 0.8648(8) 0.8459(17) 0.2987(7) 0.026(3) Uiso 1 1 d . . . H6 H 0.0630(8) 0.6403(17) 1.0328(7) 0.025(3) Uiso 1 1 d . . . H11 H 0.2165(7) 0.3756(17) 0.8083(6) 0.017(3) Uiso 1 1 d . . . H12 H 0.3474(7) 0.3768(17) 0.7935(7) 0.021(3) Uiso 1 1 d . . . H3 H 0.3060(9) 0.8748(18) 1.1932(7) 0.027(4) Uiso 1 1 d . . . H16B H 0.0955(7) 0.3446(19) 0.8908(6) 0.024(3) Uiso 1 1 d . . . H33 H 0.9726(9) 0.7268(17) 0.3878(7) 0.027(4) Uiso 1 1 d . . . H26 H 0.5568(8) 0.6216(17) 0.5233(6) 0.023(3) Uiso 1 1 d . . . H34 H 0.9509(8) 0.6122(17) 0.4907(6) 0.022(3) Uiso 1 1 d . . . H31 H 0.7311(8) 0.8617(18) 0.3096(7) 0.027(4) Uiso 1 1 d . . . H5 H 0.0601(8) 0.7736(16) 1.1387(6) 0.022(3) Uiso 1 1 d . . . H4 H 0.1801(8) 0.8818(18) 1.2194(7) 0.028(3) Uiso 1 1 d . . . H36A H 0.5678(8) 0.7611(16) 0.4196(6) 0.021(3) Uiso 1 1 d . . . H37 H 0.5701(8) 0.5616(19) 0.3246(6) 0.028(4) Uiso 1 1 d . . . H23 H 0.7950(9) 0.382(2) 0.6969(7) 0.037(4) Uiso 1 1 d . . . H13 H 0.4619(8) 0.4894(16) 0.8776(6) 0.022(3) Uiso 1 1 d . . . H36B H 0.6043(8) 0.9087(19) 0.3823(6) 0.030(4) Uiso 1 1 d . . . H18B H 0.0104(9) 0.522(2) 0.7208(8) 0.038(4) Uiso 1 1 d . . . H14 H 0.4492(8) 0.6258(18) 0.9807(7) 0.027(4) Uiso 1 1 d . . . H25 H 0.5472(8) 0.5012(17) 0.6299(6) 0.027(4) Uiso 1 1 d . . . H24 H 0.6620(8) 0.384(2) 0.7134(8) 0.038(4) Uiso 1 1 d . . . H18A H 0.0341(9) 0.334(2) 0.7698(8) 0.046(4) Uiso 1 1 d . . . H38A H 0.5334(10) 0.904(2) 0.2642(8) 0.051(5) Uiso 1 1 d . . . H38B H 0.5081(9) 0.715(2) 0.2195(8) 0.039(4) Uiso 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 O1 0.0198(5) 0.0220(5) 0.0255(5) -0.0026(4) -0.0008(4) -0.0009(4) O2 0.0244(5) 0.0235(5) 0.0285(5) 0.0009(4) -0.0041(4) 0.0034(4) C29 0.0180(6) 0.0121(6) 0.0166(6) -0.0040(5) 0.0034(5) -0.0004(5) C9 0.0176(6) 0.0119(7) 0.0162(6) 0.0035(5) 0.0030(5) 0.0008(5) C34 0.0180(7) 0.0154(7) 0.0308(7) -0.0061(6) 0.0032(6) -0.0007(5) C3 0.0307(8) 0.0142(7) 0.0189(7) 0.0011(5) 0.0026(6) 0.0003(5) C7 0.0262(7) 0.0105(6) 0.0167(6) 0.0043(5) 0.0059(5) 0.0032(5) C2 0.0232(7) 0.0110(7) 0.0190(6) 0.0044(5) 0.0030(5) 0.0017(5) C30 0.0187(6) 0.0112(7) 0.0190(6) -0.0046(5) 0.0035(5) -0.0011(5) C35 0.0199(6) 0.0124(6) 0.0197(6) -0.0046(5) 0.0047(5) -0.0027(5) N2 0.0159(5) 0.0148(6) 0.0182(5) -0.0010(4) 0.0015(4) 0.0001(4) C5 0.0304(8) 0.0164(7) 0.0251(7) 0.0021(6) 0.0127(6) 0.0019(6) C31 0.0251(7) 0.0134(7) 0.0216(7) -0.0029(5) 0.0072(6) -0.0021(5) C32 0.0311(8) 0.0168(7) 0.0287(7) -0.0052(6) 0.0149(6) -0.0058(6) C4 0.0363(8) 0.0163(7) 0.0188(7) 0.0011(5) 0.0110(6) 0.0019(6) C6 0.0247(7) 0.0148(7) 0.0212(7) 0.0029(5) 0.0077(6) 0.0016(5) N1 0.0170(5) 0.0148(6) 0.0163(5) 0.0003(4) 0.0019(4) 0.0008(4) C36 0.0178(7) 0.0193(8) 0.0202(7) -0.0002(5) 0.0044(6) 0.0035(5) C37 0.0139(6) 0.0199(8) 0.0221(7) -0.0008(5) 0.0042(5) 0.0007(5) C1 0.0201(7) 0.0115(7) 0.0181(6) 0.0024(5) -0.0001(5) 0.0007(5) C17 0.0126(6) 0.0195(8) 0.0227(7) 0.0008(5) 0.0026(5) 0.0013(5) C14 0.0190(7) 0.0155(7) 0.0232(7) 0.0037(5) 0.0026(5) 0.0005(5) C10 0.0189(6) 0.0104(6) 0.0178(6) 0.0051(5) 0.0033(5) 0.0019(5) C8 0.0149(6) 0.0127(6) 0.0195(6) 0.0046(5) 0.0032(5) 0.0020(5) C15 0.0214(7) 0.0123(6) 0.0166(6) 0.0037(5) 0.0055(5) 0.0036(5) C16 0.0169(6) 0.0176(8) 0.0204(6) 0.0005(5) 0.0048(5) -0.0004(5) C21 0.0237(7) 0.0120(7) 0.0196(6) -0.0029(5) -0.0024(5) 0.0008(5) C22 0.0285(7) 0.0109(7) 0.0196(6) -0.0040(5) 0.0032(5) -0.0025(5) C28 0.0150(6) 0.0130(6) 0.0195(6) -0.0054(5) 0.0023(5) -0.0003(5) C26 0.0270(7) 0.0165(7) 0.0240(7) -0.0055(5) 0.0096(6) -0.0049(5) C27 0.0256(7) 0.0114(6) 0.0170(6) -0.0051(5) 0.0057(5) -0.0038(5) C13 0.0198(7) 0.0184(7) 0.0288(7) 0.0032(6) 0.0100(6) 0.0024(5) C11 0.0207(7) 0.0131(7) 0.0180(6) 0.0027(5) 0.0043(5) 0.0019(5) C38 0.0252(7) 0.0341(9) 0.0231(8) 0.0003(6) 0.0042(6) 0.0044(6) C12 0.0236(7) 0.0164(7) 0.0201(7) 0.0021(5) 0.0088(5) 0.0027(5) C18 0.0253(7) 0.0314(9) 0.0230(7) -0.0021(6) 0.0034(6) -0.0024(6) C23 0.0445(9) 0.0141(7) 0.0213(7) -0.0013(5) 0.0058(6) -0.0025(6) C25 0.0383(8) 0.0208(7) 0.0292(7) -0.0075(6) 0.0168(7) -0.0098(6) C24 0.0510(9) 0.0203(8) 0.0220(7) -0.0022(6) 0.0159(7) -0.0090(6) C33 0.0216(7) 0.0190(7) 0.0397(8) -0.0085(6) 0.0146(6) -0.0054(5) _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 C1 1.2208(15) . ? O2 C21 1.2199(15) . ? C29 C28 1.3598(17) . ? C29 C30 1.4633(17) . ? C29 C36 1.4992(17) . ? C9 C8 1.3573(16) . ? C9 C10 1.4639(16) . ? C9 C16 1.5000(17) . ? C34 C35 1.3861(17) . ? C34 C33 1.3863(19) . ? C34 H34 0.962(13) . ? C3 C2 1.3797(17) . ? C3 C4 1.3923(19) . ? C3 H3 0.961(14) . ? C7 C6 1.3919(18) . ? C7 C2 1.4107(17) . ? C7 C8 1.4578(17) . ? C2 C1 1.4886(17) . ? C30 C31 1.3924(17) . ? C30 C35 1.4140(17) . ? C35 N2 1.3967(15) . ? N2 C21 1.3916(15) . ? N2 C28 1.3993(16) . ? C5 C6 1.3903(18) . ? C5 C4 1.3904(19) . ? C5 H5 0.998(13) . ? C31 C32 1.3875(18) . ? C31 H31 0.996(14) . ? C32 C33 1.401(2) . ? C32 H32 0.996(13) . ? C4 H4 0.989(14) . ? C6 H6 1.011(14) . ? N1 C1 1.3949(15) . ? N1 C15 1.3993(15) . ? N1 C8 1.4026(16) . ? C36 C37 1.5010(17) . ? C36 H36A 0.978(13) . ? C36 H36B 0.995(14) . ? C37 C38 1.3150(18) . ? C37 H37 0.998(14) . ? C17 C18 1.3147(18) . ? C17 C16 1.5037(17) . ? C17 H17 0.994(14) . ? C14 C15 1.3847(17) . ? C14 C13 1.3905(18) . ? C14 H14 0.989(14) . ? C10 C11 1.3920(17) . ? C10 C15 1.4132(17) . ? C16 H16A 0.977(12) . ? C16 H16B 0.996(14) . ? C21 C22 1.4894(18) . ? C22 C23 1.3827(18) . ? C22 C27 1.4113(17) . ? C28 C27 1.4586(17) . ? C26 C27 1.3882(18) . ? C26 C25 1.3912(18) . ? C26 H26 1.031(13) . ? C13 C12 1.3981(18) . ? C13 H13 0.978(13) . ? C11 C12 1.3882(17) . ? C11 H11 1.011(13) . ? C38 H38A 0.983(18) . ? C38 H38B 0.990(15) . ? C12 H12 0.973(13) . ? C18 H18B 0.997(15) . ? C18 H18A 0.998(18) . ? C23 C24 1.391(2) . ? C23 H23 1.015(15) . ? C25 C24 1.389(2) . ? C25 H25 1.001(13) . ? C24 H24 0.975(15) . ? C33 H33 0.973(14) . ? 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 C28 C29 C30 106.34(10) . . ? C28 C29 C36 127.10(11) . . ? C30 C29 C36 126.56(11) . . ? C8 C9 C10 106.15(10) . . ? C8 C9 C16 127.97(11) . . ? C10 C9 C16 125.88(10) . . ? C35 C34 C33 117.02(12) . . ? C35 C34 H34 120.5(7) . . ? C33 C34 H34 122.4(7) . . ? C2 C3 C4 118.15(12) . . ? C2 C3 H3 121.6(8) . . ? C4 C3 H3 120.2(8) . . ? C6 C7 C2 119.93(11) . . ? C6 C7 C8 132.91(11) . . ? C2 C7 C8 107.15(10) . . ? C3 C2 C7 121.54(12) . . ? C3 C2 C1 129.10(11) . . ? C7 C2 C1 109.35(10) . . ? C31 C30 C35 118.95(11) . . ? C31 C30 C29 133.17(11) . . ? C35 C30 C29 107.87(10) . . ? C34 C35 N2 130.78(11) . . ? C34 C35 C30 122.73(11) . . ? N2 C35 C30 106.49(10) . . ? C21 N2 C35 137.65(10) . . ? C21 N2 C28 113.05(10) . . ? C35 N2 C28 109.29(10) . . ? C6 C5 C4 121.47(13) . . ? C6 C5 H5 119.2(7) . . ? C4 C5 H5 119.3(7) . . ? C32 C31 C30 118.88(12) . . ? C32 C31 H31 118.7(7) . . ? C30 C31 H31 122.4(7) . . ? C31 C32 C33 120.97(13) . . ? C31 C32 H32 120.6(7) . . ? C33 C32 H32 118.4(7) . . ? C5 C4 C3 120.69(12) . . ? C5 C4 H4 119.1(8) . . ? C3 C4 H4 120.2(8) . . ? C5 C6 C7 118.22(12) . . ? C5 C6 H6 119.9(7) . . ? C7 C6 H6 121.9(7) . . ? C1 N1 C15 137.63(10) . . ? C1 N1 C8 113.09(10) . . ? C15 N1 C8 109.26(9) . . ? C29 C36 C37 113.99(10) . . ? C29 C36 H36A 109.6(7) . . ? C37 C36 H36A 107.9(7) . . ? C29 C36 H36B 110.3(8) . . ? C37 C36 H36B 107.7(7) . . ? H36A C36 H36B 107.1(10) . . ? C38 C37 C36 123.91(13) . . ? C38 C37 H37 121.7(7) . . ? C36 C37 H37 114.4(7) . . ? O1 C1 N1 125.53(11) . . ? O1 C1 C2 130.55(11) . . ? N1 C1 C2 103.92(10) . . ? C18 C17 C16 124.15(13) . . ? C18 C17 H17 120.4(7) . . ? C16 C17 H17 115.4(7) . . ? C15 C14 C13 116.92(11) . . ? C15 C14 H14 121.4(7) . . ? C13 C14 H14 121.7(8) . . ? C11 C10 C15 119.08(11) . . ? C11 C10 C9 132.65(11) . . ? C15 C10 C9 108.27(10) . . ? C9 C8 N1 110.13(10) . . ? C9 C8 C7 143.38(11) . . ? N1 C8 C7 106.48(10) . . ? C14 C15 N1 131.03(11) . . ? C14 C15 C10 122.79(11) . . ? N1 C15 C10 106.18(10) . . ? C9 C16 C17 112.73(10) . . ? C9 C16 H16A 110.2(7) . . ? C17 C16 H16A 110.1(7) . . ? C9 C16 H16B 110.5(7) . . ? C17 C16 H16B 109.5(7) . . ? H16A C16 H16B 103.5(10) . . ? O2 C21 N2 125.47(12) . . ? O2 C21 C22 130.45(11) . . ? N2 C21 C22 104.06(10) . . ? C23 C22 C27 121.70(12) . . ? C23 C22 C21 129.05(11) . . ? C27 C22 C21 109.24(10) . . ? C29 C28 N2 110.00(11) . . ? C29 C28 C27 143.33(11) . . ? N2 C28 C27 106.67(10) . . ? C27 C26 C25 118.13(12) . . ? C27 C26 H26 121.5(7) . . ? C25 C26 H26 120.4(7) . . ? C26 C27 C22 119.90(11) . . ? C26 C27 C28 133.12(11) . . ? C22 C27 C28 106.97(10) . . ? C14 C13 C12 121.35(12) . . ? C14 C13 H13 119.8(7) . . ? C12 C13 H13 118.8(7) . . ? C12 C11 C10 118.69(11) . . ? C12 C11 H11 118.4(7) . . ? C10 C11 H11 122.9(7) . . ? C37 C38 H38A 119.0(9) . . ? C37 C38 H38B 123.1(9) . . ? H38A C38 H38B 117.8(13) . . ? C11 C12 C13 121.17(12) . . ? C11 C12 H12 119.8(7) . . ? C13 C12 H12 119.1(7) . . ? C17 C18 H18B 121.8(9) . . ? C17 C18 H18A 118.5(9) . . ? H18B C18 H18A 119.7(12) . . ? C22 C23 C24 117.90(13) . . ? C22 C23 H23 121.6(8) . . ? C24 C23 H23 120.5(8) . . ? C24 C25 C26 121.64(13) . . ? C24 C25 H25 119.8(7) . . ? C26 C25 H25 118.6(7) . . ? C25 C24 C23 120.73(13) . . ? C25 C24 H24 118.7(8) . . ? C23 C24 H24 120.5(8) . . ? C34 C33 C32 121.44(12) . . ? C34 C33 H33 119.7(8) . . ? C32 C33 H33 118.9(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.181 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.038