# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Jian-Wu Xie' _publ_contact_author_name 'Jian-Wu Xie' _publ_contact_author_email xiejw@zjnu.cn data_a _database_code_depnum_ccdc_archive 'CCDC 887775' #TrackingRef '- 4gb.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Cl N O8 ' _chemical_formula_sum 'C18 H20 Cl N O8' _chemical_formula_weight 413.80 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.7433(3) _cell_length_b 11.3443(4) _cell_length_c 18.2730(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2019.73(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2622 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max .36 _exptl_crystal_size_mid .26 _exptl_crystal_size_min .12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min .0000 _exptl_absorpt_correction_T_max .0000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEXII area-detector diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 17114 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4646 _reflns_number_gt 2202 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEXII (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^+0.0000P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0062(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(10) _refine_ls_number_reflns 4646 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_ref 0.1337 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Cl Cl -0.05831(12) -0.42036(11) -0.06776(7) 0.1147(5) Uani 1 1 d . . . N1 N -0.4777(2) -0.7153(2) -0.12971(14) 0.0449(6) Uani 1 1 d . . . O1 O -0.2451(2) -0.4116(2) -0.23918(14) 0.0783(8) Uani 1 1 d . . . O2 O -0.3198(3) -0.5741(2) -0.29635(15) 0.0796(8) Uani 1 1 d . . . O3 O -0.4702(3) -0.3937(2) -0.08734(17) 0.0981(9) Uani 1 1 d . . . O4 O -0.48605(19) -0.63326(17) -0.19106(11) 0.0517(6) Uani 1 1 d . . . O5 O -0.56754(19) -0.79254(19) -0.12995(12) 0.0567(6) Uani 1 1 d . . . O6 O -0.2947(2) -0.6804(2) 0.03253(12) 0.0695(7) Uani 1 1 d . . . H6D H -0.2291 -0.7113 0.0530 0.104 Uiso 1 1 calc R . . O7 O -0.1555(3) -0.8800(2) 0.00619(16) 0.0888(9) Uani 1 1 d . . . O8 O -0.3013(3) -0.9354(2) -0.08043(16) 0.0891(9) Uani 1 1 d . . . C1 C -0.1953(6) -0.6408(6) -0.3989(3) 0.160(3) Uani 1 1 d . . . H1A H -0.1456 -0.6162 -0.4416 0.239 Uiso 1 1 calc R . . H1B H -0.2715 -0.6893 -0.4134 0.239 Uiso 1 1 calc R . . H1C H -0.1356 -0.6852 -0.3675 0.239 Uiso 1 1 calc R . . C2 C -0.2433(6) -0.5429(4) -0.3620(3) 0.124(2) Uani 1 1 d . . . H2A H -0.3021 -0.4977 -0.3943 0.149 Uiso 1 1 calc R . . H2B H -0.1661 -0.4934 -0.3485 0.149 Uiso 1 1 calc R . . C3 C -0.3105(3) -0.5008(4) -0.2411(2) 0.0590(9) Uani 1 1 d . . . C4 C -0.3920(3) -0.5394(3) -0.17394(18) 0.0479(8) Uani 1 1 d . . . C5 C -0.4813(3) -0.4334(3) -0.1485(2) 0.0631(10) Uani 1 1 d . . . C6 C -0.5816(3) -0.3878(4) -0.2017(2) 0.0831(12) Uani 1 1 d . . . H6A H -0.6309 -0.3230 -0.1804 0.125 Uiso 1 1 calc R . . H6B H -0.6450 -0.4492 -0.2146 0.125 Uiso 1 1 calc R . . H6C H -0.5344 -0.3614 -0.2448 0.125 Uiso 1 1 calc R . . C7 C -0.2963(3) -0.5865(3) -0.11249(17) 0.0468(8) Uani 1 1 d . . . H7A H -0.2923 -0.5287 -0.0727 0.056 Uiso 1 1 calc R . . C8 C -0.1510(3) -0.6171(3) -0.13665(18) 0.0539(9) Uani 1 1 d . . . C9 C -0.1280(3) -0.7162(4) -0.1779(2) 0.0704(11) Uani 1 1 d . . . H9A H -0.2016 -0.7650 -0.1894 0.084 Uiso 1 1 calc R . . C10 C 0.0021(4) -0.7457(4) -0.2029(2) 0.0887(13) Uani 1 1 d . . . H10A H 0.0152 -0.8130 -0.2311 0.106 Uiso 1 1 calc R . . C11 C 0.1084(5) -0.6765(6) -0.1860(3) 0.1047(18) Uani 1 1 d . . . H11A H 0.1953 -0.6962 -0.2031 0.126 Uiso 1 1 calc R . . C12 C 0.0928(4) -0.5770(5) -0.1439(2) 0.0919(15) Uani 1 1 d . . . H12A H 0.1678 -0.5301 -0.1319 0.110 Uiso 1 1 calc R . . C13 C -0.0409(3) -0.5478(3) -0.1194(2) 0.0728(11) Uani 1 1 d . . . C14 C -0.3751(3) -0.6906(2) -0.08779(17) 0.0429(8) Uani 1 1 d . . . C15 C -0.3503(3) -0.7597(3) -0.01932(18) 0.0523(9) Uani 1 1 d . . . H15A H -0.4388 -0.7882 -0.0010 0.063 Uiso 1 1 calc R . . C16 C -0.2559(4) -0.8640(3) -0.0288(2) 0.0617(9) Uani 1 1 d . . . C17 C -0.2195(6) -1.0440(4) -0.0920(4) 0.167(3) Uani 1 1 d . . . H17A H -0.1402 -1.0261 -0.1221 0.200 Uiso 1 1 calc R . . H17B H -0.1868 -1.0732 -0.0452 0.200 Uiso 1 1 calc R . . C18 C -0.2949(8) -1.1265(6) -0.1244(5) 0.213(4) Uani 1 1 d . . . H18A H -0.2405 -1.1962 -0.1313 0.320 Uiso 1 1 calc R . . H18B H -0.3258 -1.0980 -0.1711 0.320 Uiso 1 1 calc R . . H18C H -0.3728 -1.1448 -0.0943 0.320 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 Cl 0.0996(8) 0.1114(9) 0.1331(10) -0.0087(8) -0.0161(8) -0.0518(7) N1 0.0398(13) 0.0477(16) 0.0473(17) 0.0007(13) 0.0060(13) 0.0005(13) O1 0.0719(15) 0.0735(17) 0.0894(19) 0.0211(15) 0.0061(15) -0.0193(15) O2 0.103(2) 0.0718(17) 0.0646(17) 0.0081(15) 0.0278(16) 0.0060(15) O3 0.115(2) 0.0822(19) 0.097(2) -0.0161(18) -0.002(2) 0.0333(17) O4 0.0430(11) 0.0587(13) 0.0533(14) 0.0086(11) -0.0056(10) -0.0061(10) O5 0.0446(11) 0.0578(14) 0.0678(16) -0.0028(12) 0.0034(12) -0.0144(11) O6 0.0854(16) 0.0649(15) 0.0582(16) -0.0049(13) -0.0174(14) 0.0141(13) O7 0.0740(17) 0.0825(18) 0.110(2) -0.0168(16) -0.0331(16) 0.0195(15) O8 0.0932(17) 0.0597(16) 0.114(2) -0.0251(16) -0.0378(17) 0.0218(13) C1 0.201(6) 0.147(5) 0.131(5) 0.023(4) 0.093(5) 0.033(5) C2 0.194(5) 0.092(4) 0.087(3) 0.012(3) 0.077(4) 0.009(4) C3 0.049(2) 0.060(2) 0.068(3) 0.015(2) 0.003(2) 0.0097(19) C4 0.0406(16) 0.0454(19) 0.058(2) 0.0053(16) 0.0022(17) -0.0022(14) C5 0.057(2) 0.054(2) 0.078(3) 0.007(2) 0.009(2) 0.0028(18) C6 0.057(2) 0.096(3) 0.096(3) 0.019(3) 0.000(2) 0.029(2) C7 0.0418(15) 0.0458(18) 0.053(2) -0.0007(16) -0.0011(15) 0.0011(15) C8 0.0400(17) 0.062(2) 0.060(2) 0.0186(19) -0.0002(16) 0.0006(16) C9 0.055(2) 0.074(3) 0.083(3) 0.009(2) 0.010(2) 0.0153(19) C10 0.062(2) 0.105(3) 0.099(4) 0.022(3) 0.013(3) 0.028(2) C11 0.056(3) 0.162(5) 0.095(4) 0.057(4) 0.015(3) 0.034(3) C12 0.045(2) 0.135(5) 0.096(4) 0.045(3) -0.012(2) -0.016(3) C13 0.055(2) 0.082(3) 0.082(3) 0.027(2) -0.011(2) -0.015(2) C14 0.0331(15) 0.0451(18) 0.051(2) -0.0048(16) 0.0018(15) 0.0042(14) C15 0.0529(19) 0.054(2) 0.050(2) 0.0012(18) -0.0024(17) -0.0020(16) C16 0.063(2) 0.052(2) 0.070(3) 0.003(2) -0.009(2) 0.0019(19) C17 0.164(5) 0.084(4) 0.252(8) -0.083(5) -0.077(5) 0.051(4) C18 0.249(9) 0.111(5) 0.280(9) -0.070(6) -0.025(8) 0.039(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 Cl C13 1.735(4) . ? N1 O5 1.238(3) . ? N1 C14 1.290(3) . ? N1 O4 1.460(3) . ? O1 C3 1.197(4) . ? O2 C3 1.311(4) . ? O2 C2 1.456(4) . ? O3 C5 1.209(4) . ? O4 C4 1.439(3) . ? O6 C15 1.414(4) . ? O6 H6D 0.8200 . ? O7 C16 1.183(4) . ? O8 C16 1.319(4) . ? O8 C17 1.483(5) . ? C1 C2 1.382(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.526(4) . ? C4 C7 1.554(4) . ? C4 C5 1.556(4) . ? C5 C6 1.473(5) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C14 1.478(4) . ? C7 C8 1.523(4) . ? C7 H7A 0.9800 . ? C8 C13 1.367(4) . ? C8 C9 1.372(5) . ? C9 C10 1.389(5) . ? C9 H9A 0.9300 . ? C10 C11 1.336(7) . ? C10 H10A 0.9300 . ? C11 C12 1.373(6) . ? C11 H11A 0.9300 . ? C12 C13 1.417(6) . ? C12 H12A 0.9300 . ? C14 C15 1.496(4) . ? C15 C16 1.509(4) . ? C15 H15A 0.9800 . ? C17 C18 1.329(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 O5 N1 C14 134.7(3) . . ? O5 N1 O4 114.1(2) . . ? C14 N1 O4 111.1(2) . . ? C3 O2 C2 116.4(3) . . ? C4 O4 N1 105.6(2) . . ? C15 O6 H6D 109.5 . . ? C16 O8 C17 115.6(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 O2 112.4(4) . . ? C1 C2 H2A 109.1 . . ? O2 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? O2 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? O1 C3 O2 126.5(3) . . ? O1 C3 C4 119.8(4) . . ? O2 C3 C4 113.7(3) . . ? O4 C4 C3 111.6(3) . . ? O4 C4 C7 106.5(2) . . ? C3 C4 C7 111.6(2) . . ? O4 C4 C5 106.3(2) . . ? C3 C4 C5 108.0(3) . . ? C7 C4 C5 112.7(3) . . ? O3 C5 C6 122.6(3) . . ? O3 C5 C4 120.9(3) . . ? C6 C5 C4 116.4(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C14 C7 C8 112.9(3) . . ? C14 C7 C4 100.6(2) . . ? C8 C7 C4 115.2(2) . . ? C14 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C4 C7 H7A 109.2 . . ? C13 C8 C9 118.0(3) . . ? C13 C8 C7 122.2(3) . . ? C9 C8 C7 119.8(3) . . ? C8 C9 C10 121.8(4) . . ? C8 C9 H9A 119.1 . . ? C10 C9 H9A 119.1 . . ? C11 C10 C9 119.4(4) . . ? C11 C10 H10A 120.3 . . ? C9 C10 H10A 120.3 . . ? C10 C11 C12 121.8(4) . . ? C10 C11 H11A 119.1 . . ? C12 C11 H11A 119.1 . . ? C11 C12 C13 118.1(4) . . ? C11 C12 H12A 121.0 . . ? C13 C12 H12A 121.0 . . ? C8 C13 C12 121.0(4) . . ? C8 C13 Cl 121.8(3) . . ? C12 C13 Cl 117.2(3) . . ? N1 C14 C7 113.3(3) . . ? N1 C14 C15 120.5(3) . . ? C7 C14 C15 126.2(3) . . ? O6 C15 C14 106.8(2) . . ? O6 C15 C16 110.0(3) . . ? C14 C15 C16 114.4(3) . . ? O6 C15 H15A 108.5 . . ? C14 C15 H15A 108.5 . . ? C16 C15 H15A 108.5 . . ? O7 C16 O8 124.7(3) . . ? O7 C16 C15 124.2(4) . . ? O8 C16 C15 111.0(3) . . ? C18 C17 O8 110.6(5) . . ? C18 C17 H17A 109.5 . . ? O8 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? O8 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 O5 N1 O4 C4 169.5(2) . . . . ? C14 N1 O4 C4 -11.4(3) . . . . ? C3 O2 C2 C1 146.9(5) . . . . ? C2 O2 C3 O1 -0.5(5) . . . . ? C2 O2 C3 C4 -179.4(3) . . . . ? N1 O4 C4 C3 138.7(2) . . . . ? N1 O4 C4 C7 16.7(3) . . . . ? N1 O4 C4 C5 -103.7(3) . . . . ? O1 C3 C4 O4 167.7(3) . . . . ? O2 C3 C4 O4 -13.3(4) . . . . ? O1 C3 C4 C7 -73.2(4) . . . . ? O2 C3 C4 C7 105.8(3) . . . . ? O1 C3 C4 C5 51.1(4) . . . . ? O2 C3 C4 C5 -129.8(3) . . . . ? O4 C4 C5 O3 118.2(4) . . . . ? C3 C4 C5 O3 -121.9(4) . . . . ? C7 C4 C5 O3 1.9(4) . . . . ? O4 C4 C5 C6 -59.9(4) . . . . ? C3 C4 C5 C6 60.1(4) . . . . ? C7 C4 C5 C6 -176.2(3) . . . . ? O4 C4 C7 C14 -15.7(3) . . . . ? C3 C4 C7 C14 -137.8(3) . . . . ? C5 C4 C7 C14 100.5(3) . . . . ? O4 C4 C7 C8 106.0(3) . . . . ? C3 C4 C7 C8 -16.1(4) . . . . ? C5 C4 C7 C8 -137.8(3) . . . . ? C14 C7 C8 C13 -139.0(3) . . . . ? C4 C7 C8 C13 106.1(3) . . . . ? C14 C7 C8 C9 41.8(4) . . . . ? C4 C7 C8 C9 -73.0(4) . . . . ? C13 C8 C9 C10 -1.0(5) . . . . ? C7 C8 C9 C10 178.2(3) . . . . ? C8 C9 C10 C11 0.5(6) . . . . ? C9 C10 C11 C12 0.5(7) . . . . ? C10 C11 C12 C13 -1.0(7) . . . . ? C9 C8 C13 C12 0.6(5) . . . . ? C7 C8 C13 C12 -178.6(3) . . . . ? C9 C8 C13 Cl 179.9(3) . . . . ? C7 C8 C13 Cl 0.7(5) . . . . ? C11 C12 C13 C8 0.4(6) . . . . ? C11 C12 C13 Cl -178.9(3) . . . . ? O5 N1 C14 C7 179.6(3) . . . . ? O4 N1 C14 C7 0.7(3) . . . . ? O5 N1 C14 C15 -4.1(5) . . . . ? O4 N1 C14 C15 177.1(2) . . . . ? C8 C7 C14 N1 -114.1(3) . . . . ? C4 C7 C14 N1 9.3(3) . . . . ? C8 C7 C14 C15 69.8(4) . . . . ? C4 C7 C14 C15 -166.8(3) . . . . ? N1 C14 C15 O6 -146.3(3) . . . . ? C7 C14 C15 O6 29.5(4) . . . . ? N1 C14 C15 C16 91.7(3) . . . . ? C7 C14 C15 C16 -92.4(4) . . . . ? C17 O8 C16 O7 1.9(6) . . . . ? C17 O8 C16 C15 -177.3(4) . . . . ? O6 C15 C16 O7 5.0(5) . . . . ? C14 C15 C16 O7 125.1(4) . . . . ? O6 C15 C16 O8 -175.9(3) . . . . ? C14 C15 C16 O8 -55.7(4) . . . . ? C16 O8 C17 C18 158.3(6) . . . . ? 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 O6 H6D O5 0.82 2.11 2.857(3) 151.3 4_535 O6 H6D O7 0.82 2.22 2.683(3) 116.4 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.187 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.038 _publ_section_references ; Sheldrick G.M.(1996), SADABS, Absorption Correction Program, University of Goeltingen, German Siemens(1994), SAINT Software Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA Siemens(1996), SMART Software Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA Siemens(1994), SHELXTL^TM^ Version 5 Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA ;