# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Albert Moyano' _publ_contact_author_email amoyano@ub.edu loop_ _publ_author_name X.Companyo G.Valero O.Pineda T.Calvet M.Font-Bardia A.Moyano R.Rios data_raom20a _database_code_depnum_ccdc_archive 'CCDC 831712' #TrackingRef 'CIFenantiopure3a.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 N2 O2' _chemical_formula_sum 'C15 H14 N2 O2' _chemical_formula_weight 254.28 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.021(7) _cell_length_b 12.749(6) _cell_length_c 10.714(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1368.8(14) _cell_formula_units_Z 4 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 104 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 105(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 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14664 _diffrn_reflns_av_R_equivalents 0.0787 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 32.60 _reflns_number_total 4508 _reflns_number_gt 3309 _reflns_threshold_expression >2sigma(I) _computing_data_collection MARXDS _computing_cell_refinement AUTOMAR _computing_data_reduction MARSCALE _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0764P)^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 SHELXL _refine_ls_extinction_coef 0.059(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _chemical_absolute_configuration rm _refine_ls_number_reflns 4508 _refine_ls_number_parameters 189 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1577 _refine_ls_wR_factor_gt 0.1442 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.076 _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 -0.33198(12) 0.11547(11) 0.15763(14) 0.0586(3) Uani 1 1 d D . . H1O H -0.4046(16) 0.129(2) 0.123(2) 0.088 Uiso 1 1 d D . . O2 O -0.06350(13) 0.32381(11) -0.03919(14) 0.0573(3) Uani 1 1 d . . . N1 N -0.23176(14) 0.15379(12) 0.07278(15) 0.0501(3) Uani 1 1 d . . . N2 N 0.08251(15) 0.24560(12) 0.09939(16) 0.0523(4) Uani 1 1 d . . . H2N H 0.1561 0.2629 0.0636 0.063 Uiso 1 1 calc R . . C1 C -0.09292(18) 0.07336(16) -0.08877(19) 0.0550(4) Uani 1 1 d . . . H1 H -0.0995 0.1356 -0.1335 0.066 Uiso 1 1 calc R . . C2 C -0.0175(2) -0.00967(17) -0.1360(2) 0.0661(6) Uani 1 1 d . . . H2 H 0.0288 -0.0019 -0.2107 0.079 Uiso 1 1 calc R . . C3 C -0.0117(2) -0.10372(18) -0.0715(2) 0.0661(5) Uani 1 1 d . . . H3 H 0.0361 -0.1599 -0.1041 0.079 Uiso 1 1 calc R . . C4 C -0.0769(2) -0.11368(19) 0.0408(2) 0.0695(6) Uani 1 1 d . . . H4 H -0.0711 -0.1766 0.0844 0.083 Uiso 1 1 calc R . . C5 C -0.1517(2) -0.03100(16) 0.0909(2) 0.0589(4) Uani 1 1 d . . . H5 H -0.1962 -0.0388 0.1665 0.071 Uiso 1 1 calc R . . C6 C -0.15844(17) 0.06322(14) 0.02525(18) 0.0502(4) Uani 1 1 d . . . C7 C -0.14519(17) 0.22744(15) 0.14621(18) 0.0512(4) Uani 1 1 d . . . C8 C -0.2304(2) 0.31675(18) 0.1987(2) 0.0631(5) Uani 1 1 d . . . H8A H -0.2823 0.3473 0.1328 0.095 Uiso 1 1 calc R . . H8B H -0.1733 0.3693 0.2344 0.095 Uiso 1 1 calc R . . H8C H -0.2889 0.2897 0.2619 0.095 Uiso 1 1 calc R . . C9 C -0.04085(17) 0.27239(14) 0.05615(19) 0.0503(4) Uani 1 1 d . . . C10 C 0.07421(16) 0.18568(15) 0.21077(18) 0.0505(4) Uani 1 1 d . . . C11 C 0.17694(19) 0.14382(17) 0.2795(2) 0.0594(5) Uani 1 1 d . . . H11 H 0.2652 0.1510 0.2542 0.071 Uiso 1 1 calc R . . C12 C 0.1438(2) 0.08991(18) 0.3891(2) 0.0639(5) Uani 1 1 d . . . C13 C 0.0105(2) 0.07935(17) 0.4260(2) 0.0621(5) Uani 1 1 d . . . C14 C -0.0924(2) 0.12189(17) 0.3543(2) 0.0594(5) Uani 1 1 d . . . C15 C -0.05936(18) 0.17420(15) 0.24461(17) 0.0510(4) Uani 1 1 d . . . H14 H -0.188(3) 0.114(2) 0.378(2) 0.080(8) Uiso 1 1 d . . . H12 H 0.209(2) 0.046(2) 0.444(3) 0.078(7) Uiso 1 1 d . . . H13 H -0.012(2) 0.0438(18) 0.504(2) 0.062(6) 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 0.0425(5) 0.0683(8) 0.0650(8) 0.0142(7) 0.0074(6) -0.0042(6) O2 0.0519(6) 0.0579(7) 0.0622(8) 0.0111(6) -0.0025(6) 0.0002(5) N1 0.0409(6) 0.0506(8) 0.0588(9) 0.0059(7) 0.0035(6) -0.0047(5) N2 0.0410(6) 0.0569(8) 0.0589(9) 0.0082(7) 0.0023(6) -0.0008(6) C1 0.0505(9) 0.0550(9) 0.0595(10) -0.0009(8) -0.0004(8) -0.0063(7) C2 0.0542(9) 0.0675(13) 0.0767(14) -0.0120(11) 0.0015(10) -0.0065(9) C3 0.0574(10) 0.0610(11) 0.0800(14) -0.0127(10) -0.0059(10) 0.0075(9) C4 0.0660(11) 0.0629(12) 0.0795(14) 0.0031(11) -0.0114(12) 0.0036(10) C5 0.0604(10) 0.0571(10) 0.0593(10) 0.0106(9) -0.0060(9) -0.0047(9) C6 0.0417(7) 0.0505(8) 0.0586(9) 0.0034(7) 0.0018(8) 0.0011(7) C7 0.0449(7) 0.0521(9) 0.0567(9) 0.0031(8) 0.0018(8) -0.0004(7) C8 0.0548(9) 0.0624(11) 0.0722(13) -0.0040(10) 0.0022(10) 0.0047(8) C9 0.0458(8) 0.0457(8) 0.0594(10) 0.0039(8) -0.0047(8) -0.0020(6) C10 0.0439(8) 0.0529(9) 0.0549(9) 0.0032(8) -0.0027(8) -0.0017(7) C11 0.0490(9) 0.0642(11) 0.0649(11) 0.0060(9) -0.0019(9) 0.0061(8) C12 0.0608(10) 0.0647(12) 0.0663(12) 0.0088(10) -0.0028(10) 0.0054(9) C13 0.0657(11) 0.0632(12) 0.0574(11) 0.0100(9) -0.0030(10) -0.0070(9) C14 0.0559(9) 0.0637(11) 0.0587(10) 0.0060(9) 0.0007(9) -0.0023(8) C15 0.0509(9) 0.0506(9) 0.0513(9) 0.0012(7) 0.0008(8) -0.0035(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 N1 1.440(2) . ? O1 H1O 0.834(7) . ? O2 C9 1.235(2) . ? N1 C6 1.460(2) . ? N1 C7 1.501(2) . ? N2 C9 1.364(2) . ? N2 C10 1.419(3) . ? N2 H2N 0.8600 . ? C1 C6 1.393(3) . ? C1 C2 1.396(3) . ? C1 H1 0.9300 . ? C2 C3 1.385(3) . ? C2 H2 0.9300 . ? C3 C4 1.375(4) . ? C3 H3 0.9300 . ? C4 C5 1.401(3) . ? C4 H4 0.9300 . ? C5 C6 1.394(3) . ? C5 H5 0.9300 . ? C7 C15 1.520(3) . ? C7 C8 1.530(3) . ? C7 C9 1.534(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.373(3) . ? C10 C15 1.394(3) . ? C11 C12 1.400(3) . ? C11 H11 0.9300 . ? C12 C13 1.400(3) . ? C12 H12 1.04(3) . ? C13 C14 1.396(3) . ? C13 H13 0.98(2) . ? C14 C15 1.391(3) . ? C14 H14 0.99(3) . ? 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 N1 O1 H1O 105(2) . . ? O1 N1 C6 107.62(14) . . ? O1 N1 C7 106.53(14) . . ? C6 N1 C7 112.75(14) . . ? C9 N2 C10 111.55(15) . . ? C9 N2 H2N 124.2 . . ? C10 N2 H2N 124.2 . . ? C6 C1 C2 120.2(2) . . ? C6 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.4(2) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 118.8(2) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C1 C6 C5 119.99(18) . . ? C1 C6 N1 118.01(17) . . ? C5 C6 N1 121.99(17) . . ? N1 C7 C15 114.28(15) . . ? N1 C7 C8 109.62(16) . . ? C15 C7 C8 113.13(17) . . ? N1 C7 C9 107.33(15) . . ? C15 C7 C9 102.56(14) . . ? C8 C7 C9 109.48(16) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 N2 125.50(17) . . ? O2 C9 C7 126.41(16) . . ? N2 C9 C7 108.10(16) . . ? C11 C10 C15 122.64(18) . . ? C11 C10 N2 128.01(16) . . ? C15 C10 N2 109.35(15) . . ? C10 C11 C12 117.52(18) . . ? C10 C11 H11 121.2 . . ? C12 C11 H11 121.2 . . ? C13 C12 C11 120.7(2) . . ? C13 C12 H12 112.9(14) . . ? C11 C12 H12 125.9(14) . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13 118.7(15) . . ? C12 C13 H13 120.5(15) . . ? C15 C14 C13 118.40(19) . . ? C15 C14 H14 119.7(15) . . ? C13 C14 H14 121.9(15) . . ? C14 C15 C10 119.90(17) . . ? C14 C15 C7 131.68(17) . . ? C10 C15 C7 108.41(16) . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.175 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.046 # Attachment 'CIFracemic3a.txt' data_conm117a _database_code_depnum_ccdc_archive 'CCDC 831713' #TrackingRef 'CIFracemic3a.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 N2 O2' _chemical_formula_sum 'C15 H14 N2 O2' _chemical_formula_weight 254.28 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.891(7) _cell_length_b 8.626(4) _cell_length_c 10.666(8) _cell_angle_alpha 71.25(5) _cell_angle_beta 83.35(5) _cell_angle_gamma 74.83(4) _cell_volume 663.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 571 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _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 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5704 _diffrn_reflns_av_R_equivalents 0.0711 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 32.25 _reflns_number_total 3183 _reflns_number_gt 1955 _reflns_threshold_expression >2sigma(I) _computing_data_collection MARXDS _computing_cell_refinement AUTOMAR _computing_data_reduction MARSCALE _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0757P)^2^+0.0137P] 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 3183 _refine_ls_number_parameters 175 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1709 _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_restrained_S_all 1.211 _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 0.5762(2) -0.0086(2) 0.83082(16) 0.0737(5) Uani 1 1 d . . . O2 O 0.2818(2) 0.0763(2) 0.48734(15) 0.0687(5) Uani 1 1 d D . . H2 H 0.3875(17) 0.056(4) 0.451(3) 0.103 Uiso 1 1 d D . . N1 N 0.2947(2) 0.0803(2) 0.90986(17) 0.0593(5) Uani 1 1 d . . . H1 H 0.3153 0.0493 0.9929 0.071 Uiso 1 1 calc R . . N2 N 0.3642(2) -0.0007(2) 0.61522(17) 0.0613(5) Uani 1 1 d . . . C1 C 0.1262(3) 0.1634(3) 0.8557(2) 0.0556(5) Uani 1 1 d . . . C2 C -0.0321(3) 0.2072(3) 0.9240(2) 0.0671(6) Uani 1 1 d . . . H2A H -0.0392 0.1802 1.0159 0.081 Uiso 1 1 calc R . . C3 C -0.1777(4) 0.2927(3) 0.8477(3) 0.0779(7) Uani 1 1 d . . . H3 H -0.2858 0.3244 0.8889 0.094 Uiso 1 1 calc R . . C4 C -0.1653(4) 0.3313(4) 0.7126(3) 0.0847(8) Uani 1 1 d . . . H4 H -0.2661 0.3877 0.6644 0.102 Uiso 1 1 calc R . . C5 C -0.0076(3) 0.2893(3) 0.6453(3) 0.0720(6) Uani 1 1 d . . . H5 H -0.0010 0.3201 0.5532 0.086 Uiso 1 1 calc R . . C6 C 0.1403(3) 0.2000(3) 0.7191(2) 0.0590(5) Uani 1 1 d . . . C7 C 0.3286(3) 0.1375(3) 0.6781(2) 0.0600(5) Uani 1 1 d U . . C8 C 0.4174(3) 0.0567(3) 0.8152(2) 0.0579(5) Uani 1 1 d . . . C9 C 0.4145(4) 0.2780(4) 0.5941(3) 0.0790(7) Uani 1 1 d U . . H9A H 0.5335 0.2301 0.5711 0.119 Uiso 1 1 calc R . . H9B H 0.4137 0.3536 0.6435 0.119 Uiso 1 1 calc R . . H9C H 0.3503 0.3386 0.5148 0.119 Uiso 1 1 calc R . . C10 C 0.2885(3) -0.1422(3) 0.6888(2) 0.0577(5) Uani 1 1 d . . . C11 C 0.3956(3) -0.2808(3) 0.7747(2) 0.0693(6) Uani 1 1 d . . . H11 H 0.5108 -0.2804 0.7853 0.083 Uiso 1 1 calc R . . C12 C 0.3300(4) -0.4199(4) 0.8446(3) 0.0852(8) Uani 1 1 d . . . H12 H 0.4010 -0.5131 0.9022 0.102 Uiso 1 1 calc R . . C13 C 0.1585(4) -0.4196(4) 0.8281(3) 0.0902(9) Uani 1 1 d . . . H13 H 0.1139 -0.5120 0.8763 0.108 Uiso 1 1 calc R . . C14 C 0.0544(4) -0.2850(4) 0.7421(3) 0.0858(8) Uani 1 1 d U . . H14 H -0.0597 -0.2874 0.7302 0.103 Uiso 1 1 calc R . . C15 C 0.1175(3) -0.1447(3) 0.6722(3) 0.0723(6) Uani 1 1 d U . . H15 H 0.0455 -0.0525 0.6143 0.087 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 0.0630(11) 0.0911(12) 0.0693(11) -0.0276(9) -0.0045(7) -0.0170(9) O2 0.0633(10) 0.0856(12) 0.0565(9) -0.0210(8) -0.0033(7) -0.0165(9) N1 0.0603(12) 0.0660(11) 0.0531(10) -0.0197(8) -0.0027(8) -0.0151(9) N2 0.0620(11) 0.0727(12) 0.0514(10) -0.0192(8) -0.0016(8) -0.0195(9) C1 0.0537(12) 0.0562(12) 0.0584(13) -0.0181(9) -0.0009(9) -0.0153(9) C2 0.0683(15) 0.0655(14) 0.0681(14) -0.0218(10) 0.0049(11) -0.0181(11) C3 0.0653(16) 0.0795(17) 0.0854(18) -0.0253(13) 0.0031(12) -0.0135(13) C4 0.0719(18) 0.0842(19) 0.096(2) -0.0252(15) -0.0100(14) -0.0148(14) C5 0.0696(16) 0.0751(16) 0.0692(15) -0.0186(12) -0.0070(11) -0.0157(12) C6 0.0568(12) 0.0626(13) 0.0587(13) -0.0184(9) -0.0004(9) -0.0168(10) C7 0.0583(13) 0.0700(13) 0.0541(12) -0.0202(9) -0.0008(9) -0.0180(10) C8 0.0553(13) 0.0651(13) 0.0563(12) -0.0206(9) -0.0031(9) -0.0163(10) C9 0.0814(18) 0.0850(17) 0.0724(16) -0.0181(12) 0.0040(12) -0.0329(13) C10 0.0554(12) 0.0658(13) 0.0546(12) -0.0217(9) 0.0007(9) -0.0158(10) C11 0.0644(15) 0.0725(15) 0.0718(15) -0.0247(12) 0.0004(11) -0.0153(12) C12 0.085(2) 0.0765(17) 0.092(2) -0.0271(14) 0.0028(15) -0.0157(15) C13 0.096(2) 0.0832(19) 0.097(2) -0.0322(16) 0.0090(16) -0.0302(16) C14 0.084(2) 0.0930(19) 0.092(2) -0.0337(14) 0.0012(15) -0.0350(15) C15 0.0683(16) 0.0828(16) 0.0706(15) -0.0261(11) -0.0058(11) -0.0209(12) _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 1.238(3) . ? O2 N2 1.456(3) . ? O2 H2 0.876(7) . ? N1 C8 1.342(3) . ? N1 C1 1.424(3) . ? N1 H1 0.8600 . ? N2 C10 1.456(3) . ? N2 C7 1.499(3) . ? C1 C6 1.386(3) . ? C1 C2 1.397(3) . ? C2 C3 1.383(4) . ? C2 H2A 0.9300 . ? C3 C4 1.368(4) . ? C3 H3 0.9300 . ? C4 C5 1.386(4) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C5 H5 0.9300 . ? C6 C7 1.507(3) . ? C7 C9 1.523(3) . ? C7 C8 1.562(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.388(3) . ? C10 C11 1.389(3) . ? C11 C12 1.387(4) . ? C11 H11 0.9300 . ? C12 C13 1.384(4) . ? C12 H12 0.9300 . ? C13 C14 1.362(4) . ? C13 H13 0.9300 . ? C14 C15 1.385(4) . ? C14 H14 0.9300 . ? C15 H15 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 N2 O2 H2 87(2) . . ? C8 N1 C1 111.56(19) . . ? C8 N1 H1 124.2 . . ? C1 N1 H1 124.2 . . ? C10 N2 O2 107.92(17) . . ? C10 N2 C7 114.12(17) . . ? O2 N2 C7 105.35(16) . . ? C6 C1 C2 123.1(2) . . ? C6 C1 N1 109.32(19) . . ? C2 C1 N1 127.6(2) . . ? C3 C2 C1 116.4(2) . . ? C3 C2 H2A 121.8 . . ? C1 C2 H2A 121.8 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 122.2(3) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C4 C5 C6 118.1(3) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C1 C6 C5 119.0(2) . . ? C1 C6 C7 109.3(2) . . ? C5 C6 C7 131.6(2) . . ? N2 C7 C6 116.37(18) . . ? N2 C7 C9 109.85(19) . . ? C6 C7 C9 113.6(2) . . ? N2 C7 C8 105.87(18) . . ? C6 C7 C8 101.47(18) . . ? C9 C7 C8 108.88(19) . . ? O1 C8 N1 126.8(2) . . ? O1 C8 C7 124.8(2) . . ? N1 C8 C7 108.3(2) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 119.8(2) . . ? C15 C10 N2 122.3(2) . . ? C11 C10 N2 117.8(2) . . ? C12 C11 C10 119.7(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 119.8(3) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.4(3) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 119.7(3) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 120.1 . . ? _diffrn_measured_fraction_theta_max 0.681 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.212 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.042