# 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 'Richmond Sarpong' _publ_contact_author_email rsarpong@berkeley.edu loop_ _publ_author_name 'Richmond Sarpong' 'Alison Narayan' 'Stephen Heller' data_sarpong13 _database_code_depnum_ccdc_archive 'CCDC 834076' #TrackingRef '- Compound64_txt.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; sarpong13 ; _chemical_name_common sarpong13 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 Cl N2 O' _chemical_formula_weight 274.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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)/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 8.4660(3) _cell_length_b 7.2644(2) _cell_length_c 22.2712(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.0810(10) _cell_angle_gamma 90.00 _cell_volume 1364.31(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9961 _cell_measurement_theta_min 3.99 _cell_measurement_theta_max 67.84 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 2.418 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7601 _exptl_absorpt_correction_T_max 0.8685 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 1.0 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _space_group.IT_number 14 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator 'HELIOS multilayer mirrors' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 14245 _diffrn_reflns_av_R_equivalents 0.0123 _diffrn_reflns_av_sigmaI/netI 0.0083 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 68.08 _reflns_number_total 2476 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2004 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.0521P)^2^+0.9929P] 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 2476 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.17912(18) 0.6227(2) 0.39579(7) 0.0200(3) Uani 1 1 d . . . H1 H 0.1152 0.6740 0.4245 0.024 Uiso 1 1 calc R . . C2 C 0.14417(19) 0.6408(2) 0.33578(8) 0.0225(4) Uani 1 1 d . . . H2 H 0.0605 0.7127 0.3166 0.027 Uiso 1 1 calc R . . C3 C 0.25655(19) 0.5315(2) 0.30563(7) 0.0199(3) Uani 1 1 d . . . C4 C 0.37896(18) 0.4593(2) 0.35542(7) 0.0163(3) Uani 1 1 d . . . C5 C 0.39059(18) 0.2482(2) 0.35968(7) 0.0168(3) Uani 1 1 d . . . H5 H 0.4267 0.1944 0.3219 0.020 Uiso 1 1 calc R . . C6 C 0.50857(18) 0.2087(2) 0.41331(7) 0.0182(3) Uani 1 1 d . . . H6 H 0.6019 0.1379 0.4104 0.022 Uiso 1 1 calc R . . C7 C 0.47028(18) 0.2813(2) 0.46459(7) 0.0183(3) Uani 1 1 d . . . H7 H 0.5359 0.2717 0.5013 0.022 Uiso 1 1 calc R . . C8 C 0.31345(18) 0.3806(2) 0.45949(7) 0.0172(3) Uani 1 1 d . . . H8 H 0.2889 0.4342 0.4990 0.021 Uiso 1 1 calc R . . C9 C 0.22694(18) 0.1699(2) 0.37279(7) 0.0180(3) Uani 1 1 d . . . H9A H 0.1441 0.2154 0.3422 0.022 Uiso 1 1 calc R . . H9B H 0.2288 0.0338 0.3706 0.022 Uiso 1 1 calc R . . C10 C 0.18849(18) 0.2317(2) 0.43640(7) 0.0176(3) Uani 1 1 d . . . C11 C 0.02491(19) 0.3001(2) 0.43768(7) 0.0200(3) Uani 1 1 d . . . C12 C 0.54002(19) 0.5483(2) 0.34575(7) 0.0202(3) Uani 1 1 d . . . H12A H 0.6193 0.5058 0.3781 0.024 Uiso 1 1 calc R . . H12B H 0.5745 0.5040 0.3069 0.024 Uiso 1 1 calc R . . C13 C 0.5396(2) 0.7590(2) 0.34519(8) 0.0239(4) Uani 1 1 d . . . H13A H 0.4695 0.8031 0.3102 0.029 Uiso 1 1 calc R . . H13B H 0.4965 0.8049 0.3823 0.029 Uiso 1 1 calc R . . C14 C 0.7035(2) 0.8348(2) 0.34158(8) 0.0271(4) Uani 1 1 d . . . H14 H 0.7835 0.7959 0.3715 0.033 Uiso 1 1 calc R . . C15 C 0.7455(2) 0.9507(3) 0.30041(10) 0.0358(5) Uani 1 1 d . . . H15A H 0.6692 0.9931 0.2697 0.043 Uiso 1 1 calc R . . H15B H 0.8522 0.9920 0.3014 0.043 Uiso 1 1 calc R . . N1 N 0.31522(15) 0.52351(18) 0.41200(6) 0.0164(3) Uani 1 1 d . . . N2 N -0.10062(16) 0.3548(2) 0.44036(7) 0.0266(3) Uani 1 1 d . . . O1 O 0.26542(15) 0.50210(17) 0.25209(5) 0.0269(3) Uani 1 1 d . . . Cl1 Cl 0.20051(4) 0.04144(5) 0.489440(17) 0.02291(14) 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 0.0215(8) 0.0142(7) 0.0248(8) -0.0018(6) 0.0052(6) -0.0011(6) C2 0.0225(8) 0.0177(8) 0.0269(9) 0.0036(6) -0.0008(6) 0.0018(6) C3 0.0256(8) 0.0157(8) 0.0181(8) 0.0029(6) -0.0009(6) -0.0029(6) C4 0.0201(8) 0.0165(8) 0.0125(7) -0.0010(6) 0.0025(6) 0.0002(6) C5 0.0196(7) 0.0159(8) 0.0150(7) -0.0009(6) 0.0021(6) 0.0006(6) C6 0.0184(7) 0.0154(7) 0.0206(8) 0.0021(6) -0.0002(6) -0.0001(6) C7 0.0182(7) 0.0179(8) 0.0181(8) 0.0019(6) -0.0025(6) -0.0026(6) C8 0.0210(7) 0.0170(8) 0.0138(7) -0.0007(6) 0.0017(6) -0.0031(6) C9 0.0212(8) 0.0164(7) 0.0161(7) -0.0016(6) 0.0000(6) -0.0008(6) C10 0.0193(8) 0.0163(7) 0.0171(7) 0.0026(6) 0.0015(6) -0.0011(6) C11 0.0240(9) 0.0179(8) 0.0182(8) -0.0004(6) 0.0022(6) -0.0043(7) C12 0.0219(8) 0.0200(8) 0.0195(8) 0.0012(6) 0.0059(6) -0.0006(6) C13 0.0276(9) 0.0203(8) 0.0247(8) 0.0010(6) 0.0079(7) -0.0021(7) C14 0.0300(9) 0.0246(9) 0.0277(9) -0.0034(7) 0.0087(7) -0.0041(7) C15 0.0379(10) 0.0309(10) 0.0411(11) 0.0024(8) 0.0173(9) -0.0035(8) N1 0.0199(6) 0.0155(6) 0.0144(6) -0.0008(5) 0.0037(5) -0.0010(5) N2 0.0212(7) 0.0270(8) 0.0316(8) -0.0006(6) 0.0028(6) -0.0007(6) O1 0.0398(7) 0.0245(6) 0.0156(6) 0.0021(5) -0.0016(5) 0.0011(5) Cl1 0.0264(2) 0.0201(2) 0.0223(2) 0.00591(14) 0.00249(15) -0.00258(14) _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 1.349(2) . ? C1 N1 1.380(2) . ? C1 H1 0.9500 . ? C2 C3 1.449(2) . ? C2 H2 0.9500 . ? C3 O1 1.220(2) . ? C3 C4 1.541(2) . ? C4 N1 1.4890(19) . ? C4 C5 1.539(2) . ? C4 C12 1.541(2) . ? C5 C6 1.515(2) . ? C5 C9 1.549(2) . ? C5 H5 1.0000 . ? C6 C7 1.324(2) . ? C6 H6 0.9500 . ? C7 C8 1.506(2) . ? C7 H7 0.9500 . ? C8 N1 1.4829(19) . ? C8 C10 1.568(2) . ? C8 H8 1.0000 . ? C9 C10 1.548(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.474(2) . ? C10 Cl1 1.8149(16) . ? C11 N2 1.141(2) . ? C12 C13 1.531(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.502(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.317(3) . ? C14 H14 0.9500 . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? 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 N1 114.51(14) . . ? C2 C1 H1 122.7 . . ? N1 C1 H1 122.7 . . ? C1 C2 C3 108.07(14) . . ? C1 C2 H2 126.0 . . ? C3 C2 H2 126.0 . . ? O1 C3 C2 130.42(15) . . ? O1 C3 C4 123.23(15) . . ? C2 C3 C4 106.28(13) . . ? N1 C4 C5 106.60(12) . . ? N1 C4 C3 103.39(12) . . ? C5 C4 C3 114.74(13) . . ? N1 C4 C12 112.24(12) . . ? C5 C4 C12 111.95(13) . . ? C3 C4 C12 107.69(12) . . ? C6 C5 C4 105.77(12) . . ? C6 C5 C9 108.66(12) . . ? C4 C5 C9 108.92(12) . . ? C6 C5 H5 111.1 . . ? C4 C5 H5 111.1 . . ? C9 C5 H5 111.1 . . ? C7 C6 C5 114.18(14) . . ? C7 C6 H6 122.9 . . ? C5 C6 H6 122.9 . . ? C6 C7 C8 114.03(14) . . ? C6 C7 H7 123.0 . . ? C8 C7 H7 123.0 . . ? N1 C8 C7 108.93(12) . . ? N1 C8 C10 107.36(12) . . ? C7 C8 C10 105.00(12) . . ? N1 C8 H8 111.7 . . ? C7 C8 H8 111.7 . . ? C10 C8 H8 111.7 . . ? C10 C9 C5 109.28(12) . . ? C10 C9 H9A 109.8 . . ? C5 C9 H9A 109.8 . . ? C10 C9 H9B 109.8 . . ? C5 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? C11 C10 C9 112.93(13) . . ? C11 C10 C8 111.62(13) . . ? C9 C10 C8 108.04(12) . . ? C11 C10 Cl1 104.06(10) . . ? C9 C10 Cl1 111.77(11) . . ? C8 C10 Cl1 108.35(10) . . ? N2 C11 C10 178.01(17) . . ? C13 C12 C4 114.76(13) . . ? C13 C12 H12A 108.6 . . ? C4 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C4 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 111.45(14) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 125.44(18) . . ? C15 C14 H14 117.3 . . ? C13 C14 H14 117.3 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? C1 N1 C8 119.42(12) . . ? C1 N1 C4 107.39(12) . . ? C8 N1 C4 114.32(12) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.357 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.052 # Attachment '- Cpd55txt.txt' data_sarpong18 _database_code_depnum_ccdc_archive 'CCDC 834077' #TrackingRef '- Cpd55txt.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; sarpong18 ; _chemical_name_common sarpong18 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N O4' _chemical_formula_weight 285.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.2396(13) _cell_length_b 12.8939(7) _cell_length_c 10.3090(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.568(3) _cell_angle_gamma 90.00 _cell_volume 2767.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4679 _cell_measurement_theta_min 4.03 _cell_measurement_theta_max 67.34 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.820 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9080 _exptl_absorpt_correction_T_max 0.9524 _exptl_absorpt_process_details TWINABS _diffrn_refln_scan_width 1.0 _diffrn_refln_scan_rate 5 _space_group.centring_type C-centered _space_group.IT_number 15 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator 'HELIOS multilayer mirrors' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 2466 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 68.18 _reflns_number_total 2466 _reflns_number_gt 2362 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2008 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.0719P)^2^+3.1407P] 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 2466 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1257 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.47681(9) 0.22610(14) 0.4584(2) 0.0202(4) Uani 1 1 d . . . H1 H 0.5107 0.2498 0.4300 0.024 Uiso 1 1 calc R . . C2 C 0.48592(8) 0.15518(14) 0.5592(2) 0.0210(4) Uani 1 1 d . . . H2 H 0.5259 0.1265 0.6155 0.025 Uiso 1 1 calc R . . C3 C 0.42392(9) 0.13071(13) 0.56614(19) 0.0180(4) Uani 1 1 d . . . C4 C 0.37503(8) 0.20459(14) 0.4654(2) 0.0177(4) Uani 1 1 d . . . C5 C 0.31945(8) 0.15165(14) 0.3488(2) 0.0188(4) Uani 1 1 d . . . H5 H 0.2911 0.1111 0.3870 0.023 Uiso 1 1 calc R . . C6 C 0.34948(8) 0.08127(14) 0.2654(2) 0.0184(4) Uani 1 1 d . . . H6 H 0.3770 0.0264 0.3264 0.022 Uiso 1 1 calc R . . C7 C 0.29800(9) 0.03324(14) 0.1427(2) 0.0219(4) Uani 1 1 d . . . C8 C 0.35563(9) 0.13423(14) 0.0459(2) 0.0209(4) Uani 1 1 d . . . C9 C 0.38874(8) 0.14761(14) 0.2001(2) 0.0185(4) Uani 1 1 d . . . H9 H 0.4340 0.1219 0.2295 0.022 Uiso 1 1 calc R . . C10 C 0.38729(9) 0.26232(14) 0.2456(2) 0.0201(4) Uani 1 1 d . . . H10 H 0.4122 0.3085 0.2051 0.024 Uiso 1 1 calc R . . C11 C 0.31782(9) 0.29483(14) 0.2012(2) 0.0218(4) Uani 1 1 d . . . H11 H 0.3009 0.3520 0.1414 0.026 Uiso 1 1 calc R . . C12 C 0.28252(8) 0.23678(14) 0.2527(2) 0.0212(4) Uani 1 1 d . . . H12 H 0.2378 0.2476 0.2312 0.025 Uiso 1 1 calc R . . C13 C 0.34909(9) 0.27711(15) 0.5523(2) 0.0215(4) Uani 1 1 d . . . H13A H 0.3163 0.3234 0.4888 0.026 Uiso 1 1 calc R . . H13B H 0.3275 0.2345 0.6029 0.026 Uiso 1 1 calc R . . C14 C 0.40037(9) 0.34399(15) 0.6571(2) 0.0243(5) Uani 1 1 d . . . H14A H 0.4290 0.2990 0.7309 0.029 Uiso 1 1 calc R . . H14B H 0.4268 0.3786 0.6099 0.029 Uiso 1 1 calc R . . C15 C 0.37086(10) 0.42435(16) 0.7208(2) 0.0303(5) Uani 1 1 d . . . H15 H 0.3376 0.4654 0.6591 0.036 Uiso 1 1 calc R . . C16 C 0.38642(13) 0.4436(2) 0.8532(3) 0.0436(6) Uani 1 1 d . . . H16A H 0.4194 0.4046 0.9191 0.052 Uiso 1 1 calc R . . H16B H 0.3647 0.4965 0.8835 0.052 Uiso 1 1 calc R . . N1 N 0.41474(7) 0.26192(12) 0.39915(17) 0.0183(4) Uani 1 1 d . . . O1 O 0.40961(6) 0.06840(10) 0.64048(14) 0.0228(3) Uani 1 1 d . . . O2 O 0.25668(7) -0.02591(11) 0.13922(16) 0.0311(4) Uani 1 1 d . . . O3 O 0.30250(6) 0.07097(10) 0.01920(14) 0.0220(3) Uani 1 1 d . . . O4 O 0.36922(6) 0.17105(12) -0.04585(15) 0.0282(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 0.0180(8) 0.0194(9) 0.0226(10) -0.0045(7) 0.0064(8) -0.0023(7) C2 0.0178(9) 0.0206(9) 0.0208(10) -0.0019(7) 0.0022(8) 0.0010(7) C3 0.0207(9) 0.0142(8) 0.0162(9) -0.0040(7) 0.0029(7) -0.0006(7) C4 0.0170(8) 0.0162(9) 0.0185(10) 0.0001(7) 0.0046(8) -0.0002(6) C5 0.0169(8) 0.0189(9) 0.0200(10) -0.0010(7) 0.0057(8) -0.0005(7) C6 0.0173(8) 0.0164(9) 0.0198(10) 0.0003(7) 0.0044(7) 0.0009(7) C7 0.0224(9) 0.0191(9) 0.0225(10) -0.0023(8) 0.0058(8) 0.0028(7) C8 0.0202(8) 0.0204(9) 0.0214(11) -0.0001(8) 0.0067(8) 0.0054(7) C9 0.0176(8) 0.0185(9) 0.0180(10) 0.0006(7) 0.0045(8) 0.0017(7) C10 0.0226(9) 0.0173(9) 0.0193(10) 0.0016(7) 0.0060(8) -0.0003(7) C11 0.0242(9) 0.0166(9) 0.0204(10) -0.0005(7) 0.0025(8) 0.0044(7) C12 0.0178(9) 0.0211(9) 0.0210(10) -0.0037(8) 0.0024(8) 0.0034(7) C13 0.0202(9) 0.0208(9) 0.0225(10) -0.0019(8) 0.0063(8) 0.0029(7) C14 0.0252(10) 0.0215(9) 0.0237(11) -0.0038(8) 0.0056(8) 0.0019(7) C15 0.0321(11) 0.0222(10) 0.0330(12) -0.0046(9) 0.0070(10) 0.0050(8) C16 0.0585(15) 0.0378(14) 0.0334(14) -0.0073(10) 0.0151(12) 0.0145(11) N1 0.0187(7) 0.0163(7) 0.0188(8) 0.0001(6) 0.0051(7) -0.0016(6) O1 0.0264(7) 0.0199(7) 0.0196(7) 0.0017(5) 0.0050(6) -0.0036(5) O2 0.0296(7) 0.0305(8) 0.0303(8) -0.0065(6) 0.0069(7) -0.0119(6) O3 0.0207(6) 0.0220(6) 0.0201(7) -0.0020(5) 0.0030(6) 0.0022(5) O4 0.0276(7) 0.0359(8) 0.0215(8) 0.0015(6) 0.0091(6) 0.0014(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 1.345(3) . ? C1 N1 1.378(2) . ? C1 H1 0.9500 . ? C2 C3 1.440(3) . ? C2 H2 0.9500 . ? C3 O1 1.227(2) . ? C3 C4 1.541(2) . ? C4 N1 1.489(2) . ? C4 C13 1.540(3) . ? C4 C5 1.548(2) . ? C5 C12 1.513(3) . ? C5 C6 1.553(3) . ? C5 H5 1.0000 . ? C6 C7 1.509(3) . ? C6 C9 1.536(3) . ? C6 H6 1.0000 . ? C7 O2 1.185(2) . ? C7 O3 1.399(3) . ? C8 O4 1.189(3) . ? C8 O3 1.381(2) . ? C8 C9 1.508(3) . ? C9 C10 1.556(3) . ? C9 H9 1.0000 . ? C10 N1 1.483(3) . ? C10 C11 1.508(3) . ? C10 H10 1.0000 . ? C11 C12 1.323(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.531(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.496(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.309(3) . ? C15 H15 0.9500 . ? C16 H16A 0.9500 . ? C16 H16B 0.9500 . ? 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 N1 115.18(17) . . ? C2 C1 H1 122.4 . . ? N1 C1 H1 122.4 . . ? C1 C2 C3 107.48(16) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? O1 C3 C2 129.59(17) . . ? O1 C3 C4 123.31(16) . . ? C2 C3 C4 106.99(15) . . ? N1 C4 C13 111.66(15) . . ? N1 C4 C3 102.96(14) . . ? C13 C4 C3 107.66(15) . . ? N1 C4 C5 107.63(15) . . ? C13 C4 C5 111.07(14) . . ? C3 C4 C5 115.64(14) . . ? C12 C5 C4 106.88(15) . . ? C12 C5 C6 107.56(15) . . ? C4 C5 C6 107.84(14) . . ? C12 C5 H5 111.4 . . ? C4 C5 H5 111.4 . . ? C6 C5 H5 111.4 . . ? C7 C6 C9 103.98(15) . . ? C7 C6 C5 110.90(14) . . ? C9 C6 C5 109.78(15) . . ? C7 C6 H6 110.7 . . ? C9 C6 H6 110.7 . . ? C5 C6 H6 110.7 . . ? O2 C7 O3 119.94(18) . . ? O2 C7 C6 129.9(2) . . ? O3 C7 C6 110.15(16) . . ? O4 C8 O3 121.05(18) . . ? O4 C8 C9 128.78(17) . . ? O3 C8 C9 110.16(16) . . ? C8 C9 C6 104.82(15) . . ? C8 C9 C10 111.87(15) . . ? C6 C9 C10 108.78(15) . . ? C8 C9 H9 110.4 . . ? C6 C9 H9 110.4 . . ? C10 C9 H9 110.4 . . ? N1 C10 C11 108.59(16) . . ? N1 C10 C9 105.92(15) . . ? C11 C10 C9 107.47(15) . . ? N1 C10 H10 111.5 . . ? C11 C10 H10 111.5 . . ? C9 C10 H10 111.5 . . ? C12 C11 C10 114.17(17) . . ? C12 C11 H11 122.9 . . ? C10 C11 H11 122.9 . . ? C11 C12 C5 114.27(16) . . ? C11 C12 H12 122.9 . . ? C5 C12 H12 122.9 . . ? C14 C13 C4 114.43(15) . . ? C14 C13 H13A 108.7 . . ? C4 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C4 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 111.50(16) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C14 126.4(2) . . ? C16 C15 H15 116.8 . . ? C14 C15 H15 116.8 . . ? C15 C16 H16A 120.0 . . ? C15 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? C1 N1 C10 116.53(16) . . ? C1 N1 C4 107.08(14) . . ? C10 N1 C4 113.79(14) . . ? C8 O3 C7 110.69(15) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 2.113 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.066