# 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 N2 O0' _chemical_formula_weight 244.29 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8303(9) _cell_length_b 8.7435(10) _cell_length_c 10.6132(11) _cell_angle_alpha 89.682(9) _cell_angle_beta 88.864(9) _cell_angle_gamma 67.949(11) _cell_volume 673.34(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9829 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4132 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2382 _reflns_number_gt 1580 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2382 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1390 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5507(3) 0.4268(3) 0.7218(2) 0.0482(6) Uani 1 1 d . . . H1 H 0.5831 0.4971 0.7729 0.058 Uiso 1 1 calc R . . C2 C 0.3911(3) 0.4876(3) 0.6549(2) 0.0550(7) Uani 1 1 d . . . H2 H 0.3165 0.5989 0.6605 0.066 Uiso 1 1 calc R . . C3 C 0.3409(3) 0.3851(3) 0.5799(2) 0.0527(6) Uani 1 1 d . . . H3 H 0.2326 0.4267 0.5346 0.063 Uiso 1 1 calc R . . C4 C 0.4509(3) 0.2211(3) 0.5718(2) 0.0535(6) Uani 1 1 d . . . H4 H 0.4169 0.1511 0.5212 0.064 Uiso 1 1 calc R . . C5 C 0.6111(3) 0.1599(3) 0.6380(2) 0.0475(6) Uani 1 1 d . . . H5 H 0.6851 0.0485 0.6318 0.057 Uiso 1 1 calc R . . C6 C 0.6638(2) 0.2617(2) 0.71375(19) 0.0368(5) Uani 1 1 d . . . C7 C 0.8383(2) 0.1938(2) 0.7842(2) 0.0375(5) Uani 1 1 d . . . H7 H 0.8379 0.1180 0.8525 0.045 Uiso 1 1 calc R . . C8 C 1.0235(2) 0.1446(2) 0.70951(19) 0.0371(5) Uani 1 1 d . . . C9 C 1.0155(3) 0.1845(3) 0.5775(2) 0.0432(5) Uani 1 1 d . . . C10 C 1.1735(3) -0.0047(3) 0.7425(2) 0.0442(5) Uani 1 1 d . . . C11 C 0.9584(3) 0.2879(2) 0.80537(19) 0.0373(5) Uani 1 1 d . . . H11 H 0.9147 0.3983 0.7678 0.045 Uiso 1 1 calc R . . C12 C 1.0628(3) 0.2716(2) 0.9240(2) 0.0382(5) Uani 1 1 d . . . C13 C 1.2447(3) 0.2565(3) 0.9206(2) 0.0544(6) Uani 1 1 d . . . H13 H 1.3033 0.2565 0.8435 0.065 Uiso 1 1 calc R . . C14 C 1.3399(3) 0.2414(3) 1.0304(2) 0.0621(7) Uani 1 1 d . . . H14 H 1.4632 0.2291 1.0270 0.075 Uiso 1 1 calc R . . C15 C 1.2547(3) 0.2442(3) 1.1447(2) 0.0554(6) Uani 1 1 d . . . H15 H 1.3194 0.2345 1.2187 0.066 Uiso 1 1 calc R . . C16 C 1.0743(3) 0.2614(3) 1.1494(2) 0.0574(7) Uani 1 1 d . . . H16 H 1.0157 0.2639 1.2269 0.069 Uiso 1 1 calc R . . C17 C 0.9781(3) 0.2753(3) 1.0394(2) 0.0504(6) Uani 1 1 d . . . H17 H 0.8550 0.2871 1.0434 0.060 Uiso 1 1 calc R . . N1 N 1.0101(3) 0.2156(3) 0.4728(2) 0.0629(6) Uani 1 1 d . . . N2 N 1.2926(3) -0.1220(3) 0.7692(2) 0.0637(6) 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 0.0404(11) 0.0424(13) 0.0622(16) -0.0104(11) -0.0028(11) -0.0157(10) C2 0.0388(12) 0.0370(12) 0.0827(19) -0.0001(12) -0.0070(12) -0.0065(10) C3 0.0349(11) 0.0601(16) 0.0615(16) 0.0073(13) -0.0107(10) -0.0157(11) C4 0.0428(12) 0.0554(16) 0.0617(16) -0.0135(12) -0.0109(11) -0.0171(12) C5 0.0354(11) 0.0401(13) 0.0620(16) -0.0112(11) -0.0067(10) -0.0081(9) C6 0.0312(10) 0.0399(12) 0.0391(13) -0.0023(10) 0.0018(9) -0.0132(9) C7 0.0360(11) 0.0422(12) 0.0358(12) 0.0000(9) -0.0021(9) -0.0163(9) C8 0.0331(10) 0.0417(12) 0.0338(12) -0.0022(9) -0.0053(9) -0.0107(9) C9 0.0331(11) 0.0530(14) 0.0412(15) -0.0057(11) -0.0059(10) -0.0131(10) C10 0.0398(12) 0.0479(14) 0.0447(14) -0.0048(11) -0.0095(10) -0.0159(11) C11 0.0383(10) 0.0399(12) 0.0328(12) 0.0011(9) -0.0060(9) -0.0133(9) C12 0.0405(11) 0.0393(12) 0.0361(13) -0.0014(9) -0.0052(9) -0.0164(9) C13 0.0487(13) 0.0827(18) 0.0402(14) -0.0033(13) -0.0041(10) -0.0341(13) C14 0.0497(13) 0.086(2) 0.0565(17) -0.0039(14) -0.0140(12) -0.0322(13) C15 0.0671(15) 0.0580(15) 0.0437(15) 0.0008(12) -0.0194(12) -0.0257(13) C16 0.0667(15) 0.0748(17) 0.0352(14) -0.0021(12) -0.0018(11) -0.0317(13) C17 0.0452(12) 0.0667(16) 0.0413(14) -0.0029(12) -0.0036(10) -0.0232(11) N1 0.0541(12) 0.0874(17) 0.0406(14) 0.0006(12) -0.0053(10) -0.0188(11) N2 0.0488(11) 0.0550(13) 0.0795(17) -0.0031(12) -0.0207(11) -0.0095(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(3) . ? C1 C6 1.383(3) . ? C1 H1 0.9300 . ? C2 C3 1.369(3) . ? C2 H2 0.9300 . ? C3 C4 1.370(3) . ? C3 H3 0.9300 . ? C4 C5 1.371(3) . ? C4 H4 0.9300 . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 C7 1.485(3) . ? C7 C11 1.484(3) . ? C7 C8 1.551(2) . ? C7 H7 0.9800 . ? C8 C10 1.437(3) . ? C8 C9 1.439(3) . ? C8 C11 1.543(3) . ? C9 N1 1.139(3) . ? C10 N2 1.136(3) . ? C11 C12 1.492(3) . ? C11 H11 0.9800 . ? C12 C17 1.376(3) . ? C12 C13 1.379(3) . ? C13 C14 1.375(3) . ? C13 H13 0.9300 . ? C14 C15 1.368(3) . ? C14 H14 0.9300 . ? C15 C16 1.363(3) . ? C15 H15 0.9300 . ? C16 C17 1.381(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.6(2) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C3 C2 C1 120.3(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.8(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 118.4(2) . . ? C5 C6 C7 120.16(18) . . ? C1 C6 C7 121.45(19) . . ? C11 C7 C6 122.94(18) . . ? C11 C7 C8 61.05(12) . . ? C6 C7 C8 118.53(17) . . ? C11 C7 H7 114.6 . . ? C6 C7 H7 114.6 . . ? C8 C7 H7 114.6 . . ? C10 C8 C9 114.46(17) . . ? C10 C8 C11 118.59(18) . . ? C9 C8 C11 118.15(17) . . ? C10 C8 C7 119.09(17) . . ? C9 C8 C7 117.58(17) . . ? C11 C8 C7 57.35(12) . . ? N1 C9 C8 179.7(3) . . ? N2 C10 C8 179.4(2) . . ? C7 C11 C12 121.86(17) . . ? C7 C11 C8 61.60(12) . . ? C12 C11 C8 118.82(17) . . ? C7 C11 H11 114.8 . . ? C12 C11 H11 114.8 . . ? C8 C11 H11 114.8 . . ? C17 C12 C13 118.6(2) . . ? C17 C12 C11 120.53(18) . . ? C13 C12 C11 120.83(18) . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 119.6(2) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 120.6(2) . . ? C12 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.5(3) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C4 C5 C6 C7 -179.60(19) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? C2 C1 C6 C7 179.29(19) . . . . ? C5 C6 C7 C11 144.1(2) . . . . ? C1 C6 C7 C11 -35.8(3) . . . . ? C5 C6 C7 C8 71.8(2) . . . . ? C1 C6 C7 C8 -108.1(2) . . . . ? C11 C7 C8 C10 107.1(2) . . . . ? C6 C7 C8 C10 -138.9(2) . . . . ? C11 C7 C8 C9 -107.3(2) . . . . ? C6 C7 C8 C9 6.7(3) . . . . ? C6 C7 C8 C11 114.0(2) . . . . ? C10 C8 C9 N1 -16(49) . . . . ? C11 C8 C9 N1 131(49) . . . . ? C7 C8 C9 N1 -164(100) . . . . ? C9 C8 C10 N2 122(27) . . . . ? C11 C8 C10 N2 -25(27) . . . . ? C7 C8 C10 N2 -92(27) . . . . ? C6 C7 C11 C12 145.01(19) . . . . ? C8 C7 C11 C12 -108.0(2) . . . . ? C6 C7 C11 C8 -107.0(2) . . . . ? C10 C8 C11 C7 -107.96(19) . . . . ? C9 C8 C11 C7 106.3(2) . . . . ? C10 C8 C11 C12 4.8(2) . . . . ? C9 C8 C11 C12 -140.89(18) . . . . ? C7 C8 C11 C12 112.8(2) . . . . ? C7 C11 C12 C17 -46.0(3) . . . . ? C8 C11 C12 C17 -118.7(2) . . . . ? C7 C11 C12 C13 135.6(2) . . . . ? C8 C11 C12 C13 62.8(3) . . . . ? C17 C12 C13 C14 1.5(3) . . . . ? C11 C12 C13 C14 -179.9(2) . . . . ? C12 C13 C14 C15 -1.2(4) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C14 C15 C16 C17 0.3(4) . . . . ? C13 C12 C17 C16 -1.0(3) . . . . ? C11 C12 C17 C16 -179.5(2) . . . . ? C15 C16 C17 C12 0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.187 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 948733' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 N2 O' _chemical_formula_weight 272.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.3178(6) _cell_length_b 15.0624(7) _cell_length_c 8.1854(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.093(5) _cell_angle_gamma 90.00 _cell_volume 1384.71(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9708 _exptl_absorpt_correction_T_max 0.9796 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5283 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2438 _reflns_number_gt 1903 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.2539P] 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 2438 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.93322(10) 0.38522(8) 1.04270(16) 0.0601(4) Uani 1 1 d . . . C7 C 0.83450(13) 0.37104(10) 0.97034(19) 0.0437(4) Uani 1 1 d . . . C1 C 0.85853(15) 0.20859(11) 0.9993(2) 0.0502(4) Uani 1 1 d . . . H1 H 0.9294 0.2192 1.0668 0.060 Uiso 1 1 calc R . . C9 C 0.80786(13) 0.52960(10) 0.85228(18) 0.0415(4) Uani 1 1 d . . . H9 H 0.8948 0.5260 0.8587 0.050 Uiso 1 1 calc R . . C10 C 0.76476(13) 0.53356(10) 1.02309(19) 0.0426(4) Uani 1 1 d . . . C8 C 0.75466(13) 0.44824(10) 0.91810(19) 0.0442(4) Uani 1 1 d . . . H8 H 0.6743 0.4330 0.8672 0.053 Uiso 1 1 calc R . . C5 C 0.68721(15) 0.26252(11) 0.8283(2) 0.0509(4) Uani 1 1 d . . . H5 H 0.6414 0.3093 0.7811 0.061 Uiso 1 1 calc R . . C010 C 0.85497(15) 0.54536(11) 1.1631(2) 0.0484(4) Uiso 1 1 d . . . C11 C 0.75427(14) 0.58420(10) 0.71059(18) 0.0426(4) Uani 1 1 d . . . C6 C 0.79101(13) 0.27982(10) 0.93078(18) 0.0400(4) Uani 1 1 d . . . C16 C 0.63773(16) 0.57633(12) 0.6388(2) 0.0569(5) Uani 1 1 d . . . H16 H 0.5874 0.5354 0.6797 0.068 Uiso 1 1 calc R . . C12 C 0.82672(16) 0.64616(12) 0.6479(2) 0.0555(5) Uani 1 1 d . . . H12 H 0.9053 0.6523 0.6953 0.067 Uiso 1 1 calc R . . C3 C 0.71745(17) 0.10683(12) 0.8674(2) 0.0605(5) Uani 1 1 d . . . H3 H 0.6918 0.0487 0.8478 0.073 Uiso 1 1 calc R . . C2 C 0.82125(17) 0.12302(11) 0.9681(2) 0.0586(5) Uani 1 1 d . . . H2 H 0.8664 0.0759 1.0152 0.070 Uiso 1 1 calc R . . C14 C 0.6687(2) 0.69047(14) 0.4448(2) 0.0669(6) Uani 1 1 d . . . H14 H 0.6398 0.7259 0.3556 0.080 Uiso 1 1 calc R . . C018 C 0.65133(16) 0.57367(11) 1.04268(19) 0.0468(4) Uiso 1 1 d . . . C4 C 0.65106(16) 0.17599(13) 0.7953(2) 0.0614(5) Uani 1 1 d . . . H4 H 0.5820 0.1646 0.7245 0.074 Uiso 1 1 calc R . . C15 C 0.59579(19) 0.62932(14) 0.5060(2) 0.0681(6) Uani 1 1 d . . . H15 H 0.5174 0.6234 0.4577 0.082 Uiso 1 1 calc R . . C13 C 0.7839(2) 0.69908(14) 0.5156(2) 0.0679(5) Uani 1 1 d . . . H13 H 0.8336 0.7406 0.4749 0.082 Uiso 1 1 calc R . . N2 N 0.55995(14) 0.60167(11) 1.0593(2) 0.0646(4) Uani 1 1 d . . . N1 N 0.92471(14) 0.56023(11) 1.27207(19) 0.0685(5) 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 O1 0.0371(6) 0.0526(7) 0.0852(9) 0.0012(6) -0.0133(6) -0.0018(5) C7 0.0321(8) 0.0489(9) 0.0490(9) 0.0023(7) 0.0002(7) -0.0012(7) C1 0.0448(10) 0.0520(10) 0.0524(10) 0.0000(8) 0.0011(8) 0.0041(8) C9 0.0327(8) 0.0446(9) 0.0465(9) -0.0014(7) 0.0015(7) 0.0004(7) C10 0.0344(8) 0.0455(9) 0.0462(9) 0.0007(7) -0.0015(7) -0.0014(7) C8 0.0321(8) 0.0448(9) 0.0533(9) -0.0029(7) -0.0045(7) -0.0022(7) C5 0.0410(9) 0.0496(10) 0.0599(10) -0.0018(8) -0.0024(8) -0.0009(8) C11 0.0419(9) 0.0438(9) 0.0412(8) -0.0060(7) 0.0018(7) 0.0059(7) C6 0.0336(8) 0.0462(9) 0.0404(8) 0.0010(7) 0.0053(7) -0.0010(7) C16 0.0478(10) 0.0645(11) 0.0555(10) 0.0026(9) -0.0052(8) 0.0016(9) C12 0.0499(10) 0.0602(11) 0.0563(10) 0.0057(9) 0.0064(8) 0.0021(9) C3 0.0639(12) 0.0475(10) 0.0727(12) -0.0111(9) 0.0182(10) -0.0078(9) C2 0.0641(12) 0.0454(10) 0.0660(11) 0.0010(8) 0.0066(10) 0.0076(9) C14 0.0839(15) 0.0688(13) 0.0466(10) 0.0066(9) 0.0028(10) 0.0255(11) C4 0.0484(10) 0.0627(12) 0.0708(12) -0.0124(10) -0.0014(9) -0.0105(9) C15 0.0605(12) 0.0832(14) 0.0555(11) 0.0012(10) -0.0137(9) 0.0151(11) C13 0.0760(14) 0.0668(12) 0.0621(11) 0.0149(10) 0.0127(11) 0.0090(11) N2 0.0504(9) 0.0712(10) 0.0715(10) -0.0080(8) 0.0047(8) 0.0105(8) N1 0.0580(10) 0.0866(12) 0.0571(9) -0.0071(8) -0.0087(8) -0.0029(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2171(17) . ? C7 C6 1.482(2) . ? C7 C8 1.502(2) . ? C1 C2 1.370(2) . ? C1 C6 1.394(2) . ? C1 H1 0.9300 . ? C9 C11 1.488(2) . ? C9 C8 1.495(2) . ? C9 C10 1.538(2) . ? C9 H9 0.9800 . ? C10 C018 1.446(2) . ? C10 C010 1.449(2) . ? C10 C8 1.542(2) . ? C8 H8 0.9800 . ? C5 C6 1.382(2) . ? C5 C4 1.383(2) . ? C5 H5 0.9300 . ? C010 N1 1.138(2) . ? C11 C16 1.381(2) . ? C11 C12 1.382(2) . ? C16 C15 1.384(3) . ? C16 H16 0.9300 . ? C12 C13 1.383(3) . ? C12 H12 0.9300 . ? C3 C2 1.371(3) . ? C3 C4 1.374(3) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C14 C13 1.366(3) . ? C14 C15 1.372(3) . ? C14 H14 0.9300 . ? C018 N2 1.141(2) . ? C4 H4 0.9300 . ? C15 H15 0.9300 . ? C13 H13 0.9300 . ? 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 C7 C6 121.96(14) . . ? O1 C7 C8 119.11(14) . . ? C6 C7 C8 118.93(13) . . ? C2 C1 C6 120.52(16) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C11 C9 C8 126.17(13) . . ? C11 C9 C10 122.86(13) . . ? C8 C9 C10 61.12(10) . . ? C11 C9 H9 112.5 . . ? C8 C9 H9 112.5 . . ? C10 C9 H9 112.5 . . ? C018 C10 C010 114.18(14) . . ? C018 C10 C9 120.19(13) . . ? C010 C10 C9 116.90(13) . . ? C018 C10 C8 113.85(13) . . ? C010 C10 C8 122.66(13) . . ? C9 C10 C8 58.07(10) . . ? C9 C8 C7 118.84(13) . . ? C9 C8 C10 60.81(10) . . ? C7 C8 C10 119.06(13) . . ? C9 C8 H8 115.7 . . ? C7 C8 H8 115.7 . . ? C10 C8 H8 115.7 . . ? C6 C5 C4 120.34(16) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? N1 C010 C10 175.69(18) . . ? C16 C11 C12 118.62(15) . . ? C16 C11 C9 124.06(15) . . ? C12 C11 C9 117.32(14) . . ? C5 C6 C1 118.81(15) . . ? C5 C6 C7 122.83(14) . . ? C1 C6 C7 118.35(14) . . ? C11 C16 C15 120.10(18) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C11 C12 C13 120.87(18) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C2 C3 C4 120.38(17) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C1 C2 C3 120.04(17) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C13 C14 C15 119.61(17) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? N2 C018 C10 176.98(18) . . ? C3 C4 C5 119.86(17) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C14 C15 C16 120.70(19) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C9 C10 C018 15.6(2) . . . . ? C8 C9 C10 C018 -100.87(16) . . . . ? C11 C9 C10 C010 -130.12(15) . . . . ? C8 C9 C10 C010 113.38(15) . . . . ? C11 C9 C10 C8 116.50(16) . . . . ? C11 C9 C8 C7 139.51(15) . . . . ? C10 C9 C8 C7 -109.13(15) . . . . ? C11 C9 C8 C10 -111.36(17) . . . . ? O1 C7 C8 C9 39.6(2) . . . . ? C6 C7 C8 C9 -139.83(14) . . . . ? O1 C7 C8 C10 -31.1(2) . . . . ? C6 C7 C8 C10 149.50(14) . . . . ? C018 C10 C8 C9 111.86(15) . . . . ? C010 C10 C8 C9 -103.52(16) . . . . ? C018 C10 C8 C7 -139.38(15) . . . . ? C010 C10 C8 C7 5.2(2) . . . . ? C9 C10 C8 C7 108.76(16) . . . . ? C018 C10 C010 N1 -56(2) . . . . ? C9 C10 C010 N1 92(2) . . . . ? C8 C10 C010 N1 159(2) . . . . ? C8 C9 C11 C16 12.3(2) . . . . ? C10 C9 C11 C16 -63.8(2) . . . . ? C8 C9 C11 C12 -167.50(15) . . . . ? C10 C9 C11 C12 116.38(17) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? C4 C5 C6 C7 179.83(16) . . . . ? C2 C1 C6 C5 -1.3(2) . . . . ? C2 C1 C6 C7 179.17(15) . . . . ? O1 C7 C6 C5 -170.12(16) . . . . ? C8 C7 C6 C5 9.3(2) . . . . ? O1 C7 C6 C1 9.4(2) . . . . ? C8 C7 C6 C1 -171.19(14) . . . . ? C12 C11 C16 C15 0.5(3) . . . . ? C9 C11 C16 C15 -179.26(16) . . . . ? C16 C11 C12 C13 -0.2(3) . . . . ? C9 C11 C12 C13 179.56(16) . . . . ? C6 C1 C2 C3 0.7(3) . . . . ? C4 C3 C2 C1 0.9(3) . . . . ? C010 C10 C018 N2 -105(3) . . . . ? C9 C10 C018 N2 109(3) . . . . ? C8 C10 C018 N2 43(3) . . . . ? C2 C3 C4 C5 -1.9(3) . . . . ? C6 C5 C4 C3 1.3(3) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C11 C16 C15 C14 -0.4(3) . . . . ? C15 C14 C13 C12 0.2(3) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.142 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 948734'