# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_cd212341 _database_code_depnum_ccdc_archive 'CCDC 889520' #TrackingRef 'cd212341.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H15 N O4' _chemical_formula_weight 345.34 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 14.5884(15) _cell_length_b 7.8609(8) _cell_length_c 14.6943(15) _cell_angle_alpha 90.00 _cell_angle_beta 102.614(2) _cell_angle_gamma 90.00 _cell_volume 1644.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1848 _cell_measurement_theta_min 5.682 _cell_measurement_theta_max 45.522 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.313 _exptl_crystal_size_mid 0.212 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.14521 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9679 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3238 _reflns_number_gt 2271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.0107P] 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 SHELXL _refine_ls_extinction_coef 0.0058(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3238 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 N1 N -0.04149(11) 0.2838(2) 0.31854(13) 0.0651(5) Uani 1 1 d . . . O1 O 0.48368(8) -0.15650(15) 0.91430(7) 0.0523(3) Uani 1 1 d . . . O2 O 0.35299(7) 0.16790(16) 0.57516(7) 0.0513(3) Uani 1 1 d . . . H2 H 0.4078 0.1990 0.5906 0.077 Uiso 1 1 calc R . . O3 O -0.02928(10) 0.2371(3) 0.24300(11) 0.0938(6) Uani 1 1 d . . . O4 O -0.10752(11) 0.3704(2) 0.32796(11) 0.1017(6) Uani 1 1 d . . . C1 C 0.35581(10) -0.0235(2) 0.80256(10) 0.0390(4) Uani 1 1 d . . . C2 C 0.40328(11) -0.1060(2) 0.89144(10) 0.0409(4) Uani 1 1 d . . . C3 C 0.33296(11) -0.1198(2) 0.95213(11) 0.0548(5) Uani 1 1 d . . . H3A H 0.3486 -0.0412 1.0041 0.066 Uiso 1 1 calc R . . H3B H 0.3325 -0.2343 0.9766 0.066 Uiso 1 1 calc R . . C4 C 0.23805(11) -0.0764(3) 0.89167(11) 0.0561(5) Uani 1 1 d . . . H4A H 0.1981 -0.1763 0.8802 0.067 Uiso 1 1 calc R . . H4B H 0.2069 0.0106 0.9206 0.067 Uiso 1 1 calc R . . C5 C 0.26075(10) -0.0122(2) 0.80268(10) 0.0424(4) Uani 1 1 d . . . C6 C 0.19776(11) 0.0439(2) 0.72421(11) 0.0449(4) Uani 1 1 d . . . H6 H 0.1340 0.0471 0.7239 0.054 Uiso 1 1 calc R . . C7 C 0.22883(10) 0.0957(2) 0.64596(11) 0.0405(4) Uani 1 1 d . . . C8 C 0.32623(10) 0.0968(2) 0.64967(10) 0.0395(4) Uani 1 1 d . . . C9 C 0.39135(10) 0.0296(2) 0.72559(10) 0.0375(4) Uani 1 1 d . . . C10 C 0.49246(10) 0.01641(19) 0.72139(10) 0.0377(4) Uani 1 1 d . . . C11 C 0.51858(11) -0.0547(2) 0.64452(11) 0.0432(4) Uani 1 1 d . . . H11 H 0.4724 -0.0923 0.5945 0.052 Uiso 1 1 calc R . . C12 C 0.61178(12) -0.0706(2) 0.64094(12) 0.0523(5) Uani 1 1 d . . . H12 H 0.6281 -0.1206 0.5893 0.063 Uiso 1 1 calc R . . C13 C 0.68085(12) -0.0125(2) 0.71372(13) 0.0574(5) Uani 1 1 d . . . H13 H 0.7438 -0.0228 0.7113 0.069 Uiso 1 1 calc R . . C14 C 0.65621(11) 0.0604(2) 0.78975(12) 0.0520(5) Uani 1 1 d . . . H14 H 0.7027 0.1011 0.8387 0.062 Uiso 1 1 calc R . . C15 C 0.56322(10) 0.0739(2) 0.79416(11) 0.0428(4) Uani 1 1 d . . . H15 H 0.5475 0.1221 0.8465 0.051 Uiso 1 1 calc R . . C16 C 0.15964(10) 0.1459(2) 0.56018(11) 0.0417(4) Uani 1 1 d . . . C17 C 0.08101(12) 0.2402(2) 0.56651(12) 0.0561(5) Uani 1 1 d . . . H17 H 0.0733 0.2760 0.6247 0.067 Uiso 1 1 calc R . . C18 C 0.01420(12) 0.2818(2) 0.48805(13) 0.0601(5) Uani 1 1 d . . . H18 H -0.0386 0.3443 0.4930 0.072 Uiso 1 1 calc R . . C19 C 0.02658(11) 0.2301(2) 0.40297(12) 0.0507(5) Uani 1 1 d . . . C20 C 0.10224(11) 0.1345(2) 0.39368(12) 0.0541(5) Uani 1 1 d . . . H20 H 0.1089 0.0986 0.3352 0.065 Uiso 1 1 calc R . . C21 C 0.16847(11) 0.0923(2) 0.47255(11) 0.0503(5) Uani 1 1 d . . . H21 H 0.2200 0.0268 0.4669 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0376(9) 0.0861(12) 0.0635(11) 0.0184(9) -0.0066(8) -0.0068(8) O1 0.0414(7) 0.0617(8) 0.0499(7) 0.0035(6) 0.0017(5) 0.0117(6) O2 0.0328(6) 0.0765(9) 0.0417(7) 0.0135(6) 0.0020(5) -0.0086(6) O3 0.0570(9) 0.1701(17) 0.0484(9) 0.0210(10) -0.0015(7) -0.0041(9) O4 0.0659(10) 0.1256(14) 0.0973(12) 0.0137(10) -0.0179(9) 0.0347(10) C1 0.0339(8) 0.0434(9) 0.0380(8) -0.0022(7) 0.0044(7) 0.0021(7) C2 0.0394(9) 0.0424(9) 0.0381(8) -0.0044(7) 0.0021(7) 0.0006(7) C3 0.0476(10) 0.0760(13) 0.0401(9) 0.0090(9) 0.0083(8) 0.0036(9) C4 0.0431(10) 0.0805(14) 0.0455(10) 0.0115(9) 0.0116(8) 0.0084(9) C5 0.0357(9) 0.0509(10) 0.0408(9) 0.0023(7) 0.0084(7) 0.0038(7) C6 0.0299(8) 0.0582(11) 0.0463(9) 0.0034(8) 0.0079(7) 0.0024(7) C7 0.0332(8) 0.0465(9) 0.0393(9) 0.0001(7) 0.0026(7) 0.0002(7) C8 0.0356(8) 0.0468(9) 0.0351(8) -0.0001(7) 0.0057(7) -0.0036(7) C9 0.0316(8) 0.0424(9) 0.0368(8) -0.0041(7) 0.0040(7) -0.0014(6) C10 0.0331(8) 0.0399(9) 0.0393(8) 0.0023(7) 0.0060(7) -0.0007(7) C11 0.0420(9) 0.0478(10) 0.0393(9) -0.0013(7) 0.0076(7) -0.0028(7) C12 0.0505(10) 0.0597(11) 0.0516(10) -0.0017(8) 0.0216(9) 0.0036(8) C13 0.0343(9) 0.0767(13) 0.0628(12) 0.0049(10) 0.0143(9) 0.0029(9) C14 0.0344(9) 0.0659(12) 0.0517(10) 0.0013(9) 0.0005(8) -0.0043(8) C15 0.0371(9) 0.0472(10) 0.0421(9) -0.0024(7) 0.0045(7) 0.0008(7) C16 0.0318(8) 0.0489(10) 0.0426(9) 0.0036(7) 0.0040(7) -0.0022(7) C17 0.0473(11) 0.0740(12) 0.0458(10) 0.0007(9) 0.0076(8) 0.0153(9) C18 0.0424(10) 0.0727(13) 0.0627(12) 0.0069(10) 0.0059(9) 0.0163(9) C19 0.0325(9) 0.0649(12) 0.0495(11) 0.0116(9) -0.0024(8) -0.0045(8) C20 0.0374(9) 0.0795(13) 0.0425(10) -0.0023(9) 0.0026(8) -0.0035(9) C21 0.0327(9) 0.0689(12) 0.0467(10) -0.0021(8) 0.0032(7) 0.0064(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 O4 1.212(2) . ? N1 O3 1.219(2) . ? N1 C19 1.471(2) . ? O1 C2 1.2140(18) . ? O2 C8 1.3601(17) . ? O2 H2 0.8200 . ? C1 C5 1.390(2) . ? C1 C9 1.407(2) . ? C1 C2 1.487(2) . ? C2 C3 1.503(2) . ? C3 C4 1.512(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.505(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.381(2) . ? C6 C7 1.386(2) . ? C6 H6 0.9300 . ? C7 C8 1.410(2) . ? C7 C16 1.486(2) . ? C8 C9 1.401(2) . ? C9 C10 1.493(2) . ? C10 C11 1.386(2) . ? C10 C15 1.390(2) . ? C11 C12 1.378(2) . ? C11 H11 0.9300 . ? C12 C13 1.377(2) . ? C12 H12 0.9300 . ? C13 C14 1.372(2) . ? C13 H13 0.9300 . ? C14 C15 1.376(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.386(2) . ? C16 C21 1.387(2) . ? C17 C18 1.377(2) . ? C17 H17 0.9300 . ? C18 C19 1.364(2) . ? C18 H18 0.9300 . ? C19 C20 1.367(2) . ? C20 C21 1.378(2) . ? C20 H20 0.9300 . ? C21 H21 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 O4 N1 O3 123.45(17) . . ? O4 N1 C19 118.15(18) . . ? O3 N1 C19 118.39(18) . . ? C8 O2 H2 109.5 . . ? C5 C1 C9 121.66(13) . . ? C5 C1 C2 107.47(13) . . ? C9 C1 C2 130.78(13) . . ? O1 C2 C1 128.46(15) . . ? O1 C2 C3 123.76(14) . . ? C1 C2 C3 107.77(13) . . ? C2 C3 C4 106.94(13) . . ? C2 C3 H3A 110.3 . . ? C4 C3 H3A 110.3 . . ? C2 C3 H3B 110.3 . . ? C4 C3 H3B 110.3 . . ? H3A C3 H3B 108.6 . . ? C5 C4 C3 103.84(13) . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C1 120.11(14) . . ? C6 C5 C4 126.91(14) . . ? C1 C5 C4 112.87(14) . . ? C5 C6 C7 120.54(14) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 118.63(13) . . ? C6 C7 C16 119.81(13) . . ? C8 C7 C16 121.56(14) . . ? O2 C8 C9 122.14(13) . . ? O2 C8 C7 115.81(13) . . ? C9 C8 C7 122.05(14) . . ? C8 C9 C1 116.57(13) . . ? C8 C9 C10 119.83(13) . . ? C1 C9 C10 123.60(13) . . ? C11 C10 C15 117.90(14) . . ? C11 C10 C9 120.76(13) . . ? C15 C10 C9 121.34(14) . . ? C12 C11 C10 121.12(15) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 120.07(16) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 119.58(15) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 120.45(15) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 120.87(15) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? C17 C16 C21 118.07(14) . . ? C17 C16 C7 120.27(14) . . ? C21 C16 C7 121.56(14) . . ? C18 C17 C16 121.06(17) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.05(17) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C18 C19 C20 121.81(15) . . ? C18 C19 N1 119.17(17) . . ? C20 C19 N1 118.99(17) . . ? C19 C20 C21 118.81(16) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C20 C21 C16 121.17(15) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? 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 C5 C1 C2 O1 171.02(16) . . . . ? C9 C1 C2 O1 -5.6(3) . . . . ? C5 C1 C2 C3 -8.57(18) . . . . ? C9 C1 C2 C3 174.86(16) . . . . ? O1 C2 C3 C4 -168.71(16) . . . . ? C1 C2 C3 C4 10.90(19) . . . . ? C2 C3 C4 C5 -8.85(19) . . . . ? C9 C1 C5 C6 3.5(2) . . . . ? C2 C1 C5 C6 -173.49(14) . . . . ? C9 C1 C5 C4 179.84(15) . . . . ? C2 C1 C5 C4 2.89(19) . . . . ? C3 C4 C5 C6 179.91(17) . . . . ? C3 C4 C5 C1 3.8(2) . . . . ? C1 C5 C6 C7 -2.5(2) . . . . ? C4 C5 C6 C7 -178.31(16) . . . . ? C5 C6 C7 C8 -2.8(2) . . . . ? C5 C6 C7 C16 176.33(14) . . . . ? C6 C7 C8 O2 -172.37(14) . . . . ? C16 C7 C8 O2 8.6(2) . . . . ? C6 C7 C8 C9 7.3(2) . . . . ? C16 C7 C8 C9 -171.72(14) . . . . ? O2 C8 C9 C1 173.37(14) . . . . ? C7 C8 C9 C1 -6.3(2) . . . . ? O2 C8 C9 C10 -7.1(2) . . . . ? C7 C8 C9 C10 173.19(14) . . . . ? C5 C1 C9 C8 0.9(2) . . . . ? C2 C1 C9 C8 177.05(15) . . . . ? C5 C1 C9 C10 -178.60(15) . . . . ? C2 C1 C9 C10 -2.4(3) . . . . ? C8 C9 C10 C11 -48.7(2) . . . . ? C1 C9 C10 C11 130.78(16) . . . . ? C8 C9 C10 C15 131.59(16) . . . . ? C1 C9 C10 C15 -48.9(2) . . . . ? C15 C10 C11 C12 1.1(2) . . . . ? C9 C10 C11 C12 -178.63(15) . . . . ? C10 C11 C12 C13 -1.2(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C13 C14 C15 C10 -0.9(3) . . . . ? C11 C10 C15 C14 0.0(2) . . . . ? C9 C10 C15 C14 179.71(15) . . . . ? C6 C7 C16 C17 39.9(2) . . . . ? C8 C7 C16 C17 -141.00(16) . . . . ? C6 C7 C16 C21 -136.30(17) . . . . ? C8 C7 C16 C21 42.8(2) . . . . ? C21 C16 C17 C18 -0.9(3) . . . . ? C7 C16 C17 C18 -177.29(16) . . . . ? C16 C17 C18 C19 -0.6(3) . . . . ? C17 C18 C19 C20 1.7(3) . . . . ? C17 C18 C19 N1 -176.07(17) . . . . ? O4 N1 C19 C18 -1.2(3) . . . . ? O3 N1 C19 C18 179.74(18) . . . . ? O4 N1 C19 C20 -179.04(18) . . . . ? O3 N1 C19 C20 1.9(3) . . . . ? C18 C19 C20 C21 -1.2(3) . . . . ? N1 C19 C20 C21 176.53(15) . . . . ? C19 C20 C21 C16 -0.3(3) . . . . ? C17 C16 C21 C20 1.4(3) . . . . ? C7 C16 C21 C20 177.71(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.82 1.96 2.7287(15) 155.3 2_656 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.158 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.036