# 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 _publ_contact_author_name 'Prof Jie Zhang' _publ_contact_author_address ; State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences Fuzhou, Fujian, 350002, CHINA ; _publ_contact_author_email Zhangjie@fjirsm.ac.cn _publ_author_name 'Jie Zhang' data_From1 _database_code_depnum_ccdc_archive 'CCDC 822542' #TrackingRef 'Form1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 N2 O8' _chemical_formula_sum 'C18 H26 N2 O8' _chemical_formula_weight 398.41 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 7.1632(18) _cell_length_b 18.563(4) _cell_length_c 15.136(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.10(2) _cell_angle_gamma 90.00 _cell_volume 2012.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5418 _cell_measurement_theta_min 2.1943 _cell_measurement_theta_max 27.5438 _exptl_crystal_description column-like _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5911 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15322 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4439 _reflns_number_gt 3574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0728P)^2^+1.5531P] 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 4439 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1906 _refine_ls_wR_factor_gt 0.1692 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 -0.0634(3) -0.10136(11) 0.21876(16) 0.0675(6) Uani 1 1 d . . . O1W O 0.2455(3) 0.17555(11) 0.25267(15) 0.0667(6) Uani 1 1 d . . . H1A H 0.1549 0.1874 0.2187 0.100 Uiso 1 1 d R . . H1B H 0.2628 0.2092 0.2904 0.100 Uiso 1 1 d R . . O2 O -0.2809(3) -0.01698(10) 0.20512(14) 0.0540(5) Uani 1 1 d . . . O2W O 0.6141(3) 0.12672(11) 0.22873(14) 0.0595(5) Uani 1 1 d . . . H2A H 0.4962 0.1365 0.2296 0.089 Uiso 1 1 d R . . H2B H 0.6237 0.0833 0.2097 0.089 Uiso 1 1 d R . . O3W O 0.8808(3) 0.23153(11) 0.17805(15) 0.0690(6) Uani 1 1 d . . . H3A H 0.8197 0.2021 0.2098 0.104 Uiso 1 1 d R . . H3B H 0.8239 0.2373 0.1289 0.104 Uiso 1 1 d R . . O4W O 0.3141(4) 0.23914(11) 0.50086(15) 0.0752(7) Uani 1 1 d . . . H4A H 0.3291 0.1942 0.4905 0.113 Uiso 1 1 d R . . H4B H 0.3133 0.2617 0.4519 0.113 Uiso 1 1 d R . . O5W O 0.4986(3) 0.13644(11) 0.74968(14) 0.0587(5) Uani 1 1 d . . . H5A H 0.4264 0.1018 0.7617 0.088 Uiso 1 1 d R . . H5B H 0.4376 0.1713 0.7277 0.088 Uiso 1 1 d R . . O6W O 0.7957(3) 0.19171(10) 0.83788(15) 0.0631(6) Uani 1 1 d . . . H6A H 0.6982 0.1720 0.8164 0.095 Uiso 1 1 d R . . H6B H 0.8904 0.1667 0.8214 0.095 Uiso 1 1 d R . . N1 N 0.3611(3) 0.21137(10) -0.01057(13) 0.0397(5) Uani 1 1 d . . . N2 N 0.2284(4) 0.58713(12) 0.01844(19) 0.0593(6) Uani 1 1 d . . . C1 C -0.1172(4) -0.04082(13) 0.19232(17) 0.0426(5) Uani 1 1 d . . . C2 C 0.0176(3) 0.00603(11) 0.14168(15) 0.0348(5) Uani 1 1 d . . . C3 C -0.0500(3) 0.06131(12) 0.08695(15) 0.0386(5) Uani 1 1 d . . . H3 H -0.1802 0.0709 0.0847 0.046 Uiso 1 1 calc R . . C4 C 0.0716(3) 0.10191(12) 0.03630(16) 0.0406(5) Uani 1 1 d . . . H4 H 0.0239 0.1387 -0.0011 0.049 Uiso 1 1 calc R . . C5 C 0.2644(3) 0.08930(11) 0.03971(14) 0.0341(5) Uani 1 1 d . . . C6 C 0.3317(3) 0.03447(11) 0.09301(16) 0.0374(5) Uani 1 1 d . . . H6 H 0.4619 0.0248 0.0951 0.045 Uiso 1 1 calc R . . C7 C 0.2092(3) -0.00650(11) 0.14353(15) 0.0374(5) Uani 1 1 d . . . H7 H 0.2572 -0.0438 0.1800 0.045 Uiso 1 1 calc R . . C8 C 0.3980(4) 0.13250(12) -0.01724(18) 0.0438(6) Uani 1 1 d . . . H8A H 0.5278 0.1225 0.0016 0.053 Uiso 1 1 calc R . . H8B H 0.3848 0.1172 -0.0796 0.053 Uiso 1 1 calc R . . C9 C 0.2950(4) 0.24775(13) -0.08014(17) 0.0480(6) Uani 1 1 d . . . H9 H 0.2689 0.2229 -0.1336 0.058 Uiso 1 1 calc R . . C10 C 0.2645(4) 0.32073(13) -0.07515(17) 0.0499(7) Uani 1 1 d . . . H10 H 0.2198 0.3460 -0.1255 0.060 Uiso 1 1 calc R . . C11 C 0.2983(3) 0.35788(12) 0.00273(16) 0.0385(5) Uani 1 1 d . . . C12 C 0.3615(4) 0.31812(13) 0.07402(17) 0.0492(6) Uani 1 1 d . . . H12 H 0.3842 0.3412 0.1290 0.059 Uiso 1 1 calc R . . C13 C 0.3915(4) 0.24530(13) 0.06548(17) 0.0490(6) Uani 1 1 d . . . H13 H 0.4349 0.2186 0.1150 0.059 Uiso 1 1 calc R . . C14 C 0.2711(3) 0.43735(12) 0.00826(17) 0.0411(5) Uani 1 1 d . . . C15 C 0.2743(4) 0.47984(14) -0.06671(19) 0.0535(7) Uani 1 1 d . . . H15 H 0.2907 0.4586 -0.1233 0.064 Uiso 1 1 calc R . . C16 C 0.2535(5) 0.55374(15) -0.0586(2) 0.0625(8) Uani 1 1 d . . . H16 H 0.2573 0.5822 -0.1107 0.075 Uiso 1 1 calc R . . C17 C 0.2255(5) 0.54602(16) 0.0894(2) 0.0715(10) Uani 1 1 d . . . H17 H 0.2097 0.5687 0.1452 0.086 Uiso 1 1 calc R . . C18 C 0.2439(5) 0.47196(15) 0.0877(2) 0.0627(8) Uani 1 1 d . . . H18 H 0.2379 0.4450 0.1410 0.075 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 0.0590(13) 0.0450(11) 0.0986(17) 0.0311(11) 0.0219(11) 0.0081(9) O1W 0.0804(16) 0.0539(12) 0.0658(13) -0.0075(10) -0.0064(11) 0.0097(10) O2 0.0440(11) 0.0428(10) 0.0752(13) 0.0111(9) 0.0122(9) 0.0015(8) O2W 0.0642(13) 0.0477(11) 0.0667(13) -0.0097(9) -0.0007(10) -0.0008(9) O3W 0.0861(16) 0.0531(12) 0.0678(13) -0.0091(10) -0.0088(12) -0.0126(11) O4W 0.116(2) 0.0433(11) 0.0668(14) -0.0033(10) 0.0007(13) -0.0151(12) O5W 0.0514(12) 0.0513(11) 0.0732(13) 0.0119(9) -0.0079(10) -0.0083(9) O6W 0.0679(14) 0.0443(10) 0.0770(14) -0.0097(9) -0.0125(11) 0.0040(9) N1 0.0447(11) 0.0272(9) 0.0470(11) 0.0040(8) 0.0039(9) -0.0031(8) N2 0.0577(15) 0.0348(11) 0.0855(18) -0.0030(11) -0.0025(13) 0.0044(10) C1 0.0445(14) 0.0346(11) 0.0488(13) 0.0048(10) 0.0046(11) -0.0002(10) C2 0.0395(12) 0.0270(10) 0.0378(11) -0.0010(8) -0.0034(9) -0.0003(8) C3 0.0383(13) 0.0345(11) 0.0432(12) 0.0037(9) -0.0021(10) 0.0059(9) C4 0.0459(14) 0.0323(11) 0.0436(12) 0.0074(9) 0.0006(10) 0.0068(9) C5 0.0428(13) 0.0257(9) 0.0338(10) -0.0017(8) 0.0005(9) 0.0003(8) C6 0.0339(12) 0.0303(10) 0.0480(13) -0.0005(9) -0.0043(10) 0.0016(9) C7 0.0428(13) 0.0289(10) 0.0405(11) 0.0043(8) -0.0066(10) 0.0011(9) C8 0.0484(14) 0.0281(11) 0.0551(14) 0.0021(9) 0.0097(11) 0.0020(9) C9 0.0676(18) 0.0348(12) 0.0415(13) -0.0026(10) -0.0060(12) -0.0006(11) C10 0.0734(19) 0.0363(12) 0.0400(13) 0.0034(10) -0.0114(12) 0.0035(12) C11 0.0424(13) 0.0307(11) 0.0423(12) 0.0015(9) 0.0016(10) -0.0043(9) C12 0.0739(19) 0.0353(12) 0.0384(12) 0.0000(9) -0.0015(12) -0.0047(12) C13 0.0695(18) 0.0365(12) 0.0411(13) 0.0086(10) -0.0055(12) -0.0024(11) C14 0.0417(13) 0.0305(11) 0.0511(13) 0.0005(9) -0.0004(11) -0.0026(9) C15 0.077(2) 0.0352(12) 0.0483(14) 0.0029(10) -0.0145(13) -0.0044(12) C16 0.086(2) 0.0365(13) 0.0652(18) 0.0085(12) -0.0210(16) -0.0019(14) C17 0.093(3) 0.0420(15) 0.079(2) -0.0130(15) 0.0274(19) 0.0042(15) C18 0.089(2) 0.0393(14) 0.0597(17) -0.0005(12) 0.0221(16) 0.0025(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 O1 C1 1.253(3) . ? O1W H1A 0.8556 . ? O1W H1B 0.8553 . ? O2 C1 1.269(3) . ? O2W H2A 0.8640 . ? O2W H2B 0.8582 . ? O3W H3A 0.8493 . ? O3W H3B 0.8546 . ? O4W H4A 0.8558 . ? O4W H4B 0.8511 . ? O5W H5A 0.8449 . ? O5W H5B 0.8482 . ? O6W H6A 0.8529 . ? O6W H6B 0.8600 . ? N1 C13 1.330(3) . ? N1 C9 1.337(3) . ? N1 C8 1.491(3) . ? N2 C17 1.318(4) . ? N2 C16 1.333(4) . ? C1 C2 1.509(3) . ? C2 C7 1.392(3) . ? C2 C3 1.404(3) . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.402(3) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 C8 1.518(3) . ? C6 C7 1.391(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.374(3) . ? C9 H9 0.9500 . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 C14 1.490(3) . ? C12 C13 1.375(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C18 1.378(4) . ? C14 C15 1.382(4) . ? C15 C16 1.385(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.381(4) . ? C17 H17 0.9500 . ? C18 H18 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 H1A O1W H1B 108.8 . . ? H2A O2W H2B 106.3 . . ? H3A O3W H3B 109.1 . . ? H4A O4W H4B 108.8 . . ? H5A O5W H5B 110.4 . . ? H6A O6W H6B 107.6 . . ? C13 N1 C9 120.0(2) . . ? C13 N1 C8 119.7(2) . . ? C9 N1 C8 120.3(2) . . ? C17 N2 C16 116.5(2) . . ? O1 C1 O2 123.2(2) . . ? O1 C1 C2 118.8(2) . . ? O2 C1 C2 118.0(2) . . ? C7 C2 C3 118.2(2) . . ? C7 C2 C1 121.7(2) . . ? C3 C2 C1 120.0(2) . . ? C4 C3 C2 120.5(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.1(2) . . ? C6 C5 C8 120.0(2) . . ? C4 C5 C8 120.8(2) . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 121.4(2) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? N1 C8 C5 111.61(19) . . ? N1 C8 H8A 109.3 . . ? C5 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C5 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N1 C9 C10 120.7(2) . . ? N1 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C11 120.6(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 117.0(2) . . ? C12 C11 C14 121.8(2) . . ? C10 C11 C14 121.1(2) . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N1 C13 C12 121.4(2) . . ? N1 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C18 C14 C15 116.9(2) . . ? C18 C14 C11 122.0(2) . . ? C15 C14 C11 121.1(2) . . ? C14 C15 C16 119.3(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N2 C16 C15 123.6(3) . . ? N2 C16 H16 118.2 . . ? C15 C16 H16 118.2 . . ? N2 C17 C18 124.0(3) . . ? N2 C17 H17 118.0 . . ? C18 C17 H17 118.0 . . ? C14 C18 C17 119.6(3) . . ? C14 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.232 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.056 data_Form2 _database_code_depnum_ccdc_archive 'CCDC 822543' #TrackingRef 'Form2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N2 O3' _chemical_formula_sum 'C18 H16 N2 O3' _chemical_formula_weight 308.33 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 P21/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 7.338(7) _cell_length_b 23.989(19) _cell_length_c 9.246(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.977(16) _cell_angle_gamma 90.00 _cell_volume 1520(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1348 _cell_measurement_theta_min 2.9069 _cell_measurement_theta_max 27.3028 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2345 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11684 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3469 _reflns_number_gt 2331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0765P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3469 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 -0.21992(17) 0.14439(5) 0.08472(14) 0.0617(4) Uani 1 1 d . . . O1W O 0.2559(2) 0.49008(7) 0.51171(16) 0.0752(4) Uani 1 1 d . . . H1WB H 0.1895 0.4647 0.5395 0.135(11) Uiso 1 1 d R . . H1WA H 0.1813 0.5197 0.4857 0.098(9) Uiso 1 1 d R . . O2 O 0.0021(2) 0.08030(5) 0.09332(15) 0.0665(4) Uani 1 1 d . . . N1 N 0.1230(2) 0.62786(7) -0.09469(19) 0.0661(4) Uani 1 1 d . . . N2 N 0.45571(19) 0.35883(5) 0.18416(16) 0.0517(4) Uani 1 1 d . . . C1 C -0.0515(3) 0.12953(7) 0.10145(16) 0.0475(4) Uani 1 1 d . . . C2 C 0.1032(2) 0.17430(6) 0.13717(16) 0.0451(4) Uani 1 1 d . . . C3 C 0.2828(2) 0.16463(7) 0.12537(18) 0.0535(4) Uani 1 1 d . . . H3 H 0.3114 0.1288 0.0955 0.064 Uiso 1 1 calc R . . C4 C 0.4225(3) 0.20654(7) 0.15650(19) 0.0550(4) Uani 1 1 d . . . H4 H 0.5443 0.1993 0.1457 0.066 Uiso 1 1 calc R . . C5 C 0.3853(2) 0.25848(7) 0.20287(19) 0.0523(4) Uani 1 1 d . . . C6 C 0.2067(3) 0.26788(8) 0.2179(3) 0.0696(6) Uani 1 1 d . . . H6 H 0.1803 0.3032 0.2525 0.084 Uiso 1 1 calc R . . C7 C 0.0673(3) 0.22678(7) 0.1834(2) 0.0629(5) Uani 1 1 d . . . H7 H -0.0557 0.2345 0.1913 0.075 Uiso 1 1 calc R . . C8 C 0.5399(3) 0.30323(7) 0.2403(2) 0.0625(5) Uani 1 1 d . . . H8A H 0.6094 0.3048 0.3538 0.075 Uiso 1 1 calc R . . H8B H 0.6363 0.2935 0.1920 0.075 Uiso 1 1 calc R . . C9 C 0.3744(3) 0.36815(7) 0.0307(2) 0.0613(5) Uani 1 1 d . . . H9 H 0.3688 0.3388 -0.0396 0.074 Uiso 1 1 calc R . . C10 C 0.3002(3) 0.41889(7) -0.02502(19) 0.0570(4) Uani 1 1 d . . . H10 H 0.2433 0.4245 -0.1337 0.068 Uiso 1 1 calc R . . C11 C 0.3063(2) 0.46286(6) 0.07508(16) 0.0425(4) Uani 1 1 d . . . C12 C 0.3873(2) 0.45123(8) 0.23228(18) 0.0542(4) Uani 1 1 d . . . H12 H 0.3908 0.4795 0.3051 0.065 Uiso 1 1 calc R . . C13 C 0.4621(3) 0.39994(7) 0.28386(19) 0.0566(4) Uani 1 1 d . . . H13 H 0.5195 0.3932 0.3921 0.068 Uiso 1 1 calc R . . C14 C 0.2371(2) 0.51928(6) 0.01733(17) 0.0440(4) Uani 1 1 d . . . C15 C 0.1673(3) 0.53158(7) -0.13952(19) 0.0559(4) Uani 1 1 d . . . H15 H 0.1571 0.5030 -0.2131 0.067 Uiso 1 1 calc R . . C16 C 0.1131(3) 0.58501(8) -0.1884(2) 0.0641(5) Uani 1 1 d . . . H16 H 0.0650 0.5919 -0.2968 0.077 Uiso 1 1 calc R . . C17 C 0.1845(3) 0.61562(8) 0.0554(2) 0.0680(5) Uani 1 1 d . . . H17 H 0.1890 0.6449 0.1257 0.082 Uiso 1 1 calc R . . C18 C 0.2419(3) 0.56345(7) 0.11584(19) 0.0583(5) Uani 1 1 d . . . H18 H 0.2846 0.5576 0.2245 0.070 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 0.0466(7) 0.0674(8) 0.0617(8) -0.0063(6) 0.0080(6) 0.0002(6) O1W 0.0590(9) 0.0853(10) 0.0864(10) -0.0124(8) 0.0321(7) -0.0033(8) O2 0.0719(9) 0.0512(7) 0.0746(9) -0.0080(6) 0.0241(7) 0.0025(6) N1 0.0673(11) 0.0628(9) 0.0676(10) 0.0032(8) 0.0233(8) 0.0019(8) N2 0.0417(8) 0.0560(8) 0.0502(8) -0.0020(6) 0.0075(6) -0.0040(6) C1 0.0523(10) 0.0533(9) 0.0313(7) -0.0001(6) 0.0083(7) 0.0054(8) C2 0.0449(9) 0.0499(8) 0.0355(8) 0.0030(6) 0.0081(6) 0.0085(7) C3 0.0571(11) 0.0506(9) 0.0536(10) -0.0008(7) 0.0210(8) 0.0107(8) C4 0.0501(10) 0.0604(10) 0.0558(10) 0.0032(8) 0.0205(8) 0.0101(8) C5 0.0449(9) 0.0560(9) 0.0502(10) 0.0030(7) 0.0098(7) 0.0046(8) C6 0.0534(11) 0.0547(10) 0.1007(16) -0.0178(10) 0.0274(10) 0.0036(9) C7 0.0446(10) 0.0583(10) 0.0849(13) -0.0098(9) 0.0222(9) 0.0063(8) C8 0.0464(10) 0.0630(11) 0.0674(12) 0.0035(9) 0.0074(9) 0.0045(8) C9 0.0679(12) 0.0587(10) 0.0465(10) -0.0105(8) 0.0073(8) -0.0027(9) C10 0.0635(11) 0.0605(10) 0.0373(9) -0.0070(7) 0.0061(8) -0.0061(9) C11 0.0328(7) 0.0566(9) 0.0376(8) -0.0050(7) 0.0120(6) -0.0082(7) C12 0.0514(10) 0.0681(10) 0.0398(9) -0.0076(8) 0.0123(7) 0.0027(9) C13 0.0518(10) 0.0712(11) 0.0405(9) -0.0021(8) 0.0088(7) 0.0026(9) C14 0.0339(8) 0.0573(9) 0.0406(8) -0.0059(7) 0.0131(6) -0.0083(7) C15 0.0606(11) 0.0613(10) 0.0419(9) -0.0056(7) 0.0134(8) -0.0017(9) C16 0.0665(12) 0.0725(11) 0.0477(10) 0.0041(9) 0.0136(9) 0.0013(10) C17 0.0778(14) 0.0616(11) 0.0649(12) -0.0110(9) 0.0258(10) -0.0011(10) C18 0.0669(12) 0.0635(10) 0.0434(9) -0.0069(8) 0.0183(8) -0.0031(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 O1 C1 1.241(2) . ? O1W H1WB 0.8737 . ? O1W H1WA 0.8760 . ? O2 C1 1.256(2) . ? N1 C17 1.330(3) . ? N1 C16 1.330(2) . ? N2 C13 1.339(2) . ? N2 C9 1.346(2) . ? N2 C8 1.483(2) . ? C1 C2 1.511(2) . ? C2 C3 1.380(3) . ? C2 C7 1.385(2) . ? C3 C4 1.390(3) . ? C3 H3 0.9500 . ? C4 C5 1.376(2) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 C8 1.509(3) . ? C6 C7 1.374(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.358(3) . ? C9 H9 0.9500 . ? C10 C11 1.393(2) . ? C10 H10 0.9500 . ? C11 C12 1.388(2) . ? C11 C14 1.477(2) . ? C12 C13 1.362(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 C18 1.390(2) . ? C15 C16 1.370(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.374(3) . ? C17 H17 0.9500 . ? C18 H18 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 H1WB O1W H1WA 106.5 . . ? C17 N1 C16 115.38(17) . . ? C13 N2 C9 119.74(15) . . ? C13 N2 C8 120.92(15) . . ? C9 N2 C8 119.34(14) . . ? O1 C1 O2 125.57(16) . . ? O1 C1 C2 117.37(15) . . ? O2 C1 C2 117.05(16) . . ? C3 C2 C7 117.99(16) . . ? C3 C2 C1 121.82(15) . . ? C7 C2 C1 120.19(16) . . ? C2 C3 C4 121.07(16) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.37(17) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 118.60(16) . . ? C4 C5 C8 119.93(17) . . ? C6 C5 C8 121.45(16) . . ? C7 C6 C5 120.83(17) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C2 121.09(18) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? N2 C8 C5 112.00(15) . . ? N2 C8 H8A 109.2 . . ? C5 C8 H8A 109.2 . . ? N2 C8 H8B 109.2 . . ? C5 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N2 C9 C10 121.02(15) . . ? N2 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 120.89(16) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 116.32(16) . . ? C12 C11 C14 121.73(14) . . ? C10 C11 C14 121.90(15) . . ? C13 C12 C11 121.08(15) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? N2 C13 C12 120.92(16) . . ? N2 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C18 115.90(16) . . ? C15 C14 C11 121.60(14) . . ? C18 C14 C11 122.49(15) . . ? C16 C15 C14 119.96(16) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N1 C16 C15 124.52(18) . . ? N1 C16 H16 117.7 . . ? C15 C16 H16 117.7 . . ? N1 C17 C18 124.45(17) . . ? N1 C17 H17 117.8 . . ? C18 C17 H17 117.8 . . ? C17 C18 C14 119.74(17) . . ? C17 C18 H18 120.1 . . ? C14 C18 H18 120.1 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.192 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.034