# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_alb117 _database_code_depnum_ccdc_archive 'CCDC 870677' #TrackingRef 'alb117.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O' _chemical_formula_sum 'C15 H13 N3 O' _chemical_formula_weight 251.28 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' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.9056(6) _cell_length_b 7.3192(3) _cell_length_c 13.5734(6) _cell_angle_alpha 90.00 _cell_angle_beta 117.911(6) _cell_angle_gamma 90.00 _cell_volume 1220.77(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2251 _cell_measurement_theta_min 3.3091 _cell_measurement_theta_max 24.0614 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1682 _exptl_crystal_size_mid 0.1288 _exptl_crystal_size_min 0.0397 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.807 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5503 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 24.11 _reflns_number_total 1933 _reflns_number_gt 1557 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^ > 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^)+(0.0497P)^2^+0.3967P] 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 1933 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.67676(14) 0.1625(2) 0.71711(15) 0.0174(4) Uani 1 1 d . . . C2 C 0.68240(15) 0.2149(3) 0.81771(16) 0.0217(5) Uani 1 1 d . . . H2 H 0.7503 0.2163 0.8837 0.026 Uiso 1 1 calc R . . C3 C 0.58780(16) 0.2651(3) 0.82097(17) 0.0259(5) Uani 1 1 d . . . H3 H 0.5914 0.3025 0.8896 0.031 Uiso 1 1 calc R . . C8 C 0.48877(16) 0.2616(3) 0.72625(17) 0.0254(5) Uani 1 1 d . . . H8 H 0.4246 0.2982 0.7292 0.030 Uiso 1 1 calc R . . C7 C 0.48343(16) 0.2043(3) 0.62646(17) 0.0255(5) Uani 1 1 d . . . H7 H 0.4151 0.1989 0.5611 0.031 Uiso 1 1 calc R . . C6 C 0.57698(15) 0.1551(3) 0.62150(16) 0.0218(5) Uani 1 1 d . . . H6 H 0.5730 0.1163 0.5529 0.026 Uiso 1 1 calc R . . N1 N 0.77375(12) 0.1210(2) 0.71043(12) 0.0161(4) Uani 1 1 d . . . C5 C 0.88287(14) 0.1388(2) 0.79216(15) 0.0170(4) Uani 1 1 d . . . O O 0.91549(10) 0.18388(17) 0.89102(10) 0.0211(3) Uani 1 1 d . . . C4 C 0.94016(14) 0.0926(2) 0.73222(15) 0.0167(4) Uani 1 1 d . . . C9 C 1.05786(14) 0.0932(2) 0.77174(15) 0.0175(4) Uani 1 1 d . . . C10 C 1.12788(15) 0.0312(3) 0.87892(16) 0.0202(4) Uani 1 1 d . . . H10 H 1.0990 -0.0124 0.9256 0.024 Uiso 1 1 calc R . . C11 C 1.23953(15) 0.0328(3) 0.91768(17) 0.0254(5) Uani 1 1 d . . . H11 H 1.2867 -0.0109 0.9905 0.030 Uiso 1 1 calc R . . C12 C 1.28280(16) 0.0978(3) 0.85098(17) 0.0261(5) Uani 1 1 d . . . H12 H 1.3593 0.0975 0.8774 0.031 Uiso 1 1 calc R . . C13 C 1.21377(16) 0.1633(3) 0.74550(17) 0.0254(5) Uani 1 1 d . . . H13 H 1.2433 0.2095 0.6999 0.030 Uiso 1 1 calc R . . C14 C 1.10242(15) 0.1621(3) 0.70580(16) 0.0208(5) Uani 1 1 d . . . H14 H 1.0559 0.2083 0.6335 0.025 Uiso 1 1 calc R . . C15 C 0.87914(15) -0.0193(3) 0.53495(15) 0.0206(4) Uani 1 1 d . . . H15A H 0.8137 -0.0850 0.4825 0.031 Uiso 1 1 calc R . . H15B H 0.9417 -0.1023 0.5635 0.031 Uiso 1 1 calc R . . H15C H 0.8924 0.0835 0.4966 0.031 Uiso 1 1 calc R . . N2 N 0.76251(12) 0.0656(2) 0.61002(12) 0.0183(4) Uani 1 1 d . . . N3 N 0.86375(12) 0.0494(2) 0.62766(12) 0.0170(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 0.0188(10) 0.0169(10) 0.0215(10) 0.0025(8) 0.0135(8) -0.0004(8) C2 0.0201(10) 0.0268(11) 0.0198(10) -0.0045(9) 0.0107(8) -0.0039(8) C3 0.0257(11) 0.0313(12) 0.0281(11) -0.0065(9) 0.0189(9) -0.0019(9) C8 0.0218(11) 0.0265(11) 0.0355(12) 0.0022(10) 0.0199(9) 0.0024(8) C7 0.0172(10) 0.0324(12) 0.0262(11) 0.0071(9) 0.0094(9) 0.0010(8) C6 0.0217(11) 0.0286(11) 0.0181(10) 0.0007(9) 0.0119(9) -0.0004(8) N1 0.0173(8) 0.0197(8) 0.0144(8) 0.0003(7) 0.0101(6) -0.0007(6) C5 0.0183(10) 0.0165(10) 0.0182(10) -0.0004(8) 0.0101(8) -0.0008(7) O 0.0197(7) 0.0278(8) 0.0174(7) -0.0047(6) 0.0102(6) -0.0014(6) C4 0.0190(10) 0.0163(10) 0.0163(10) 0.0022(8) 0.0096(8) 0.0008(7) C9 0.0196(10) 0.0131(9) 0.0229(10) -0.0040(8) 0.0124(8) -0.0010(7) C10 0.0231(10) 0.0167(10) 0.0232(10) -0.0029(8) 0.0130(8) -0.0010(8) C11 0.0223(11) 0.0230(11) 0.0262(11) -0.0042(9) 0.0075(9) 0.0012(8) C12 0.0170(10) 0.0298(11) 0.0324(12) -0.0115(10) 0.0123(9) -0.0020(9) C13 0.0250(11) 0.0297(11) 0.0295(12) -0.0103(9) 0.0196(9) -0.0060(9) C14 0.0227(11) 0.0214(10) 0.0212(10) -0.0042(8) 0.0128(9) -0.0025(8) C15 0.0225(10) 0.0258(11) 0.0180(10) -0.0014(8) 0.0131(8) 0.0009(8) N2 0.0192(9) 0.0223(9) 0.0165(8) 0.0011(7) 0.0109(7) 0.0011(6) N3 0.0175(8) 0.0194(8) 0.0182(8) 0.0020(7) 0.0117(7) 0.0011(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 C2 1.385(3) . ? C1 C6 1.388(3) . ? C1 N1 1.426(2) . ? C2 C3 1.386(3) . ? C2 H2 0.9500 . ? C3 C8 1.376(3) . ? C3 H3 0.9500 . ? C8 C7 1.386(3) . ? C8 H8 0.9500 . ? C7 C6 1.382(3) . ? C7 H7 0.9500 . ? C6 H6 0.9500 . ? N1 N2 1.359(2) . ? N1 C5 1.405(2) . ? C5 O 1.243(2) . ? C5 C4 1.421(3) . ? C4 N3 1.353(2) . ? C4 C9 1.464(3) . ? C9 C10 1.394(3) . ? C9 C14 1.400(3) . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.381(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N3 1.461(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N2 N3 1.318(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 C2 C1 C6 120.22(17) . . ? C2 C1 N1 120.20(16) . . ? C6 C1 N1 119.56(16) . . ? C1 C2 C3 119.23(18) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C8 C3 C2 120.99(19) . . ? C8 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C8 C7 119.41(18) . . ? C3 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C6 C7 C8 120.37(18) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C6 C1 119.74(18) . . ? C7 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N2 N1 C5 113.22(14) . . ? N2 N1 C1 117.33(14) . . ? C5 N1 C1 129.34(15) . . ? O C5 N1 126.19(17) . . ? O C5 C4 131.48(17) . . ? N1 C5 C4 102.33(15) . . ? N3 C4 C5 106.30(16) . . ? N3 C4 C9 125.39(16) . . ? C5 C4 C9 128.29(17) . . ? C10 C9 C14 118.86(17) . . ? C10 C9 C4 119.74(17) . . ? C14 C9 C4 121.35(17) . . ? C11 C10 C9 120.27(18) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 120.46(19) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 119.48(18) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C14 C13 C12 120.64(18) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C9 120.26(18) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 N2 N1 103.46(13) . . ? N2 N3 C4 114.66(14) . . ? N2 N3 C15 116.68(14) . . ? C4 N3 C15 128.61(15) . . ? 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 -2.0(3) . . . . ? N1 C1 C2 C3 176.18(17) . . . . ? C1 C2 C3 C8 0.7(3) . . . . ? C2 C3 C8 C7 1.0(3) . . . . ? C3 C8 C7 C6 -1.5(3) . . . . ? C8 C7 C6 C1 0.2(3) . . . . ? C2 C1 C6 C7 1.6(3) . . . . ? N1 C1 C6 C7 -176.66(17) . . . . ? C2 C1 N1 N2 178.19(16) . . . . ? C6 C1 N1 N2 -3.6(2) . . . . ? C2 C1 N1 C5 -6.0(3) . . . . ? C6 C1 N1 C5 172.24(18) . . . . ? N2 N1 C5 O -178.55(17) . . . . ? C1 N1 C5 O 5.5(3) . . . . ? N2 N1 C5 C4 1.26(19) . . . . ? C1 N1 C5 C4 -174.72(16) . . . . ? O C5 C4 N3 178.21(19) . . . . ? N1 C5 C4 N3 -1.59(19) . . . . ? O C5 C4 C9 -2.9(3) . . . . ? N1 C5 C4 C9 177.30(17) . . . . ? N3 C4 C9 C10 -141.37(19) . . . . ? C5 C4 C9 C10 39.9(3) . . . . ? N3 C4 C9 C14 41.4(3) . . . . ? C5 C4 C9 C14 -137.3(2) . . . . ? C14 C9 C10 C11 -2.0(3) . . . . ? C4 C9 C10 C11 -179.35(17) . . . . ? C9 C10 C11 C12 0.7(3) . . . . ? C10 C11 C12 C13 0.7(3) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C12 C13 C14 C9 -0.5(3) . . . . ? C10 C9 C14 C13 1.9(3) . . . . ? C4 C9 C14 C13 179.20(17) . . . . ? C5 N1 N2 N3 -0.40(19) . . . . ? C1 N1 N2 N3 176.11(14) . . . . ? N1 N2 N3 C4 -0.74(19) . . . . ? N1 N2 N3 C15 176.71(14) . . . . ? C5 C4 N3 N2 1.6(2) . . . . ? C9 C4 N3 N2 -177.37(16) . . . . ? C5 C4 N3 C15 -175.54(17) . . . . ? C9 C4 N3 C15 5.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.11 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.172 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.047