# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email kaj@chem.au.dk _publ_contact_author_name 'Karl Anker Joergensen' loop_ _publ_author_name D.Cruz P.Sanchez-Murcia K.Jorgensen data_12jo0007s _database_code_depnum_ccdc_archive 'CCDC 872154' #TrackingRef 'web_deposit_cif_file_0_HaoJiang_1332178165.12jo0007s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Cl N O5' _chemical_formula_weight 367.82 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' Cl Cl 0.1484 0.1585 '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' _cell_length_a 10.1884(3) _cell_length_b 8.84867(18) _cell_length_c 10.8335(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.663(4) _cell_angle_gamma 90.00 _cell_volume 901.26(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 3524 _diffrn_reflns_av_R_equivalents 0.0116 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.59 _reflns_number_total 2659 _reflns_number_gt 2530 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_number_reflns 2659 _refine_ls_number_parameters 230 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0269 _refine_ls_R_factor_gt 0.0252 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 0.703 _refine_ls_restrained_S_all 0.703 _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 Cl1 Cl -0.19295(4) -0.31816(5) -0.24579(4) 0.02003(12) Uani 1 1 d . . . O1 O -1.28602(13) 0.04322(15) -0.82212(11) 0.0159(3) Uani 1 1 d . . . O2 O -1.09111(13) 0.04030(15) -0.88500(11) 0.0156(3) Uani 1 1 d . . . O3 O -0.76273(15) -0.25080(16) -0.66068(12) 0.0201(3) Uani 1 1 d . . . O4 O -0.99858(14) -0.22415(15) -0.74577(11) 0.0181(3) Uani 1 1 d . . . C5 C -0.47855(17) -0.3140(2) -0.32309(14) 0.0162(3) Uani 1 1 d . . . H5 H -0.4704 -0.4171 -0.2966 0.019 Uiso 1 1 calc R . . O6 O -0.78077(15) 0.10823(15) -0.42600(12) 0.0205(3) Uani 1 1 d . . . N7 N -0.87756(16) -0.09018(18) -0.56292(13) 0.0147(3) Uani 1 1 d . . . C8 C -0.35858(18) -0.2306(2) -0.30907(15) 0.0153(3) Uani 1 1 d . . . C9 C -0.76236(19) -0.0147(2) -0.46639(15) 0.0151(3) Uani 1 1 d . . . C10 C -1.36277(18) 0.1463(2) -0.92784(16) 0.0177(4) Uani 1 1 d . . . H10A H -1.4258 0.2099 -0.8991 0.021 Uiso 1 1 calc R . . H10B H -1.4233 0.0882 -1.0075 0.021 Uiso 1 1 calc R . . C11 C -1.10472(19) -0.1315(2) -0.72319(16) 0.0147(3) Uani 1 1 d . . . H11 H -1.1705 -0.1982 -0.6991 0.018 Uiso 1 1 calc R . . C12 C -0.49942(19) -0.0088(2) -0.39181(15) 0.0159(3) Uani 1 1 d . . . H12 H -0.5067 0.0960 -0.4126 0.019 Uiso 1 1 calc R . . C13 C -0.36641(19) -0.0778(2) -0.34094(16) 0.0169(3) Uani 1 1 d . . . H13 H -0.2827 -0.0217 -0.3283 0.020 Uiso 1 1 calc R . . C14 C -1.18931(18) -0.0492(2) -0.85418(15) 0.0140(3) Uani 1 1 d . . . C15 C -1.15745(19) 0.1434(2) -0.99422(16) 0.0183(4) Uani 1 1 d . . . H15A H -1.2085 0.0854 -1.0771 0.022 Uiso 1 1 calc R . . H15B H -1.0834 0.2050 -1.0085 0.022 Uiso 1 1 calc R . . C16 C -0.62156(18) -0.0922(2) -0.41231(15) 0.0142(3) Uani 1 1 d . . . C17 C -1.2653(2) -0.1649(2) -0.96248(17) 0.0202(4) Uani 1 1 d . . . H17A H -1.3225 -0.1123 -1.0455 0.030 Uiso 1 1 calc R . . H17B H -1.3274 -0.2276 -0.9335 0.030 Uiso 1 1 calc R . . H17C H -1.1948 -0.2291 -0.9781 0.030 Uiso 1 1 calc R . . C18 C -1.2626(2) 0.2480(2) -0.96533(17) 0.0189(4) Uani 1 1 d . . . C19 C -0.86727(19) -0.1936(2) -0.65605(15) 0.0156(3) Uani 1 1 d . . . C20 C -1.02259(18) -0.0293(2) -0.60333(14) 0.0142(3) Uani 1 1 d . . . H20 H -1.0257 0.0782 -0.6330 0.017 Uiso 1 1 calc R . . C21 C -0.61045(19) -0.2448(2) -0.37629(16) 0.0161(3) Uani 1 1 d . . . H21 H -0.6938 -0.3012 -0.3884 0.019 Uiso 1 1 calc R . . C22 C -1.3492(2) 0.3364(3) -1.09252(19) 0.0265(4) Uani 1 1 d . . . H22A H -1.4161 0.4036 -1.0744 0.040 Uiso 1 1 calc R . . H22B H -1.4020 0.2655 -1.1639 0.040 Uiso 1 1 calc R . . H22C H -1.2847 0.3966 -1.1205 0.040 Uiso 1 1 calc R . . C23 C -1.07887(19) -0.0418(2) -0.49206(16) 0.0189(4) Uani 1 1 d . . . H23A H -1.0228 0.0235 -0.4173 0.028 Uiso 1 1 calc R . . H23B H -1.0712 -0.1468 -0.4612 0.028 Uiso 1 1 calc R . . H23C H -1.1788 -0.0103 -0.5262 0.028 Uiso 1 1 calc R . . C24 C -1.1831(2) 0.3570(2) -0.85085(19) 0.0257(4) Uani 1 1 d . . . H24A H -1.1293 0.2991 -0.7700 0.039 Uiso 1 1 calc R . . H24B H -1.2517 0.4226 -0.8336 0.039 Uiso 1 1 calc R . . H24C H -1.1174 0.4190 -0.8758 0.039 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 Cl1 0.01487(18) 0.0249(2) 0.01930(18) -0.00095(17) 0.00542(14) 0.00489(17) O1 0.0148(6) 0.0196(7) 0.0141(5) 0.0030(5) 0.0067(4) 0.0033(5) O2 0.0121(6) 0.0191(7) 0.0149(5) 0.0039(5) 0.0043(4) 0.0003(5) O3 0.0216(7) 0.0207(7) 0.0175(5) -0.0015(5) 0.0069(5) 0.0069(5) O4 0.0207(7) 0.0143(6) 0.0151(5) -0.0023(5) 0.0022(5) 0.0044(5) C5 0.0186(7) 0.0144(8) 0.0149(6) -0.0004(7) 0.0058(6) 0.0010(8) O6 0.0225(7) 0.0166(7) 0.0199(5) -0.0049(5) 0.0055(5) 0.0040(6) N7 0.0161(7) 0.0145(8) 0.0128(6) 0.0002(5) 0.0048(5) 0.0032(6) C8 0.0149(8) 0.0205(9) 0.0097(6) -0.0011(6) 0.0039(6) 0.0039(7) C9 0.0162(8) 0.0156(9) 0.0129(6) 0.0017(6) 0.0049(6) 0.0008(7) C10 0.0134(7) 0.0234(10) 0.0149(7) 0.0036(7) 0.0039(6) 0.0045(7) C11 0.0158(8) 0.0136(8) 0.0132(7) 0.0004(6) 0.0039(6) 0.0017(7) C12 0.0191(8) 0.0132(8) 0.0155(7) 0.0013(6) 0.0067(6) -0.0012(7) C13 0.0139(8) 0.0200(9) 0.0159(7) -0.0015(7) 0.0050(6) -0.0033(7) C14 0.0118(8) 0.0158(9) 0.0141(7) 0.0001(7) 0.0047(6) 0.0013(7) C15 0.0165(8) 0.0224(10) 0.0159(7) 0.0055(7) 0.0061(6) 0.0028(7) C16 0.0148(8) 0.0163(9) 0.0106(6) -0.0010(6) 0.0038(6) 0.0018(7) C17 0.0191(8) 0.0230(10) 0.0155(7) -0.0043(7) 0.0034(6) -0.0026(7) C18 0.0185(9) 0.0214(10) 0.0159(7) 0.0057(7) 0.0058(7) 0.0036(7) C19 0.0217(9) 0.0116(8) 0.0129(7) 0.0009(6) 0.0061(6) 0.0018(7) C20 0.0148(8) 0.0125(8) 0.0132(6) 0.0004(6) 0.0030(6) 0.0030(7) C21 0.0157(8) 0.0167(9) 0.0152(7) -0.0007(6) 0.0053(6) -0.0026(7) C22 0.0291(10) 0.0293(11) 0.0218(8) 0.0112(8) 0.0107(8) 0.0135(9) C23 0.0190(8) 0.0220(10) 0.0162(7) 0.0010(7) 0.0074(6) 0.0049(7) C24 0.0302(11) 0.0186(10) 0.0257(9) 0.0007(8) 0.0080(9) 0.0003(9) _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 Cl1 C8 1.7398(18) . ? O1 C14 1.423(2) . ? O1 C10 1.437(2) . ? O2 C14 1.413(2) . ? O2 C15 1.440(2) . ? O3 C19 1.197(2) . ? O4 C19 1.344(2) . ? O4 C11 1.451(2) . ? C5 C21 1.384(2) . ? C5 C8 1.386(2) . ? O6 C9 1.214(2) . ? N7 C19 1.396(2) . ? N7 C9 1.404(2) . ? N7 C20 1.472(2) . ? C8 C13 1.389(3) . ? C9 C16 1.491(2) . ? C10 C18 1.528(3) . ? C11 C14 1.531(2) . ? C11 C20 1.539(2) . ? C12 C16 1.389(2) . ? C12 C13 1.392(2) . ? C14 C17 1.524(2) . ? C15 C18 1.536(3) . ? C16 C21 1.398(3) . ? C18 C24 1.533(3) . ? C18 C22 1.534(2) . ? C20 C23 1.525(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 C14 O1 C10 112.69(11) . . ? C14 O2 C15 113.47(13) . . ? C19 O4 C11 111.32(13) . . ? C21 C5 C8 118.92(18) . . ? C19 N7 C9 125.19(14) . . ? C19 N7 C20 111.81(13) . . ? C9 N7 C20 120.16(15) . . ? C5 C8 C13 121.84(17) . . ? C5 C8 Cl1 119.11(14) . . ? C13 C8 Cl1 119.03(14) . . ? O6 C9 N7 119.60(16) . . ? O6 C9 C16 121.97(16) . . ? N7 C9 C16 118.38(16) . . ? O1 C10 C18 111.80(14) . . ? O4 C11 C14 107.61(12) . . ? O4 C11 C20 106.03(13) . . ? C14 C11 C20 115.54(15) . . ? C16 C12 C13 120.36(16) . . ? C8 C13 C12 118.63(17) . . ? O2 C14 O1 110.82(14) . . ? O2 C14 C17 112.97(13) . . ? O1 C14 C17 112.32(14) . . ? O2 C14 C11 106.78(13) . . ? O1 C14 C11 104.05(11) . . ? C17 C14 C11 109.36(15) . . ? O2 C15 C18 110.95(13) . . ? C12 C16 C21 119.83(16) . . ? C12 C16 C9 119.03(16) . . ? C21 C16 C9 121.07(16) . . ? C10 C18 C24 110.74(14) . . ? C10 C18 C22 109.10(16) . . ? C24 C18 C22 110.32(17) . . ? C10 C18 C15 106.81(16) . . ? C24 C18 C15 110.58(16) . . ? C22 C18 C15 109.22(14) . . ? O3 C19 O4 122.59(15) . . ? O3 C19 N7 128.54(16) . . ? O4 C19 N7 108.87(14) . . ? N7 C20 C23 112.22(13) . . ? N7 C20 C11 101.12(13) . . ? C23 C20 C11 112.10(15) . . ? C5 C21 C16 120.33(17) . . ? _diffrn_measured_fraction_theta_max 0.845 _diffrn_reflns_theta_full 28.59 _diffrn_measured_fraction_theta_full 0.845 _refine_diff_density_max 0.258 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.038