# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'Jones, Simon' 'Atherton, J. C. Christian' _publ_contact_author_name 'Dr Simon Jones' _publ_contact_author_address ; Department of Chemistry University of Newcastle upon Tyne Bedson Building Newcastle upon Tyne Tyne and Wear NE1 7RU UNITED KINGDOM ; _publ_contact_author_email 'S.JONES@NCL.AC.UK' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; Mechanistic Investigations in Diastereoselective Diels-Alder Additions of Chiral 9-Anthranylethanol Derivatives ; data_compound5 _database_code_CSD 189242 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 O4' _chemical_formula_weight 334.35 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' '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 9.5923(8) _cell_length_b 10.1129(8) _cell_length_c 10.9661(9) _cell_angle_alpha 112.886(2) _cell_angle_beta 94.278(2) _cell_angle_gamma 117.285(2) _cell_volume 828.41(12) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 4879 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.26 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.092 _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 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5885 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2885 _reflns_number_gt 2332 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0388P)^2^+0.5015P] 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 0.013(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2885 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _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 0.2543(3) -0.0219(3) 0.1484(2) 0.0249(5) Uani 1 1 d . . . H1 H 0.1681 -0.0400 0.0830 0.030 Uiso 1 1 calc R . . C2 C 0.2237(3) -0.1400(3) 0.1945(3) 0.0309(6) Uani 1 1 d . . . H2 H 0.1159 -0.2373 0.1616 0.037 Uiso 1 1 calc R . . C3 C 0.3487(3) -0.1168(3) 0.2876(3) 0.0333(6) Uani 1 1 d . . . H3 H 0.3266 -0.1979 0.3187 0.040 Uiso 1 1 calc R . . C4 C 0.5065(3) 0.0250(3) 0.3358(2) 0.0277(5) Uani 1 1 d . . . H4 H 0.5931 0.0405 0.3987 0.033 Uiso 1 1 calc R . . C5 C 0.7915(3) 0.6040(3) 0.5022(2) 0.0280(5) Uani 1 1 d . . . H5 H 0.8743 0.6143 0.5649 0.034 Uiso 1 1 calc R . . C6 C 0.7729(3) 0.7403(3) 0.5310(2) 0.0320(6) Uani 1 1 d . . . H6 H 0.8425 0.8441 0.6143 0.038 Uiso 1 1 calc R . . C7 C 0.6537(3) 0.7255(3) 0.4391(2) 0.0295(5) Uani 1 1 d . . . H7 H 0.6428 0.8199 0.4593 0.035 Uiso 1 1 calc R . . C8 C 0.5493(3) 0.5745(3) 0.3173(2) 0.0228(5) Uani 1 1 d . . . H8 H 0.4683 0.5660 0.2542 0.027 Uiso 1 1 calc R . . C9 C 0.7034(3) 0.2992(3) 0.3298(2) 0.0225(5) Uani 1 1 d . . . H9 H 0.7904 0.3136 0.3989 0.027 Uiso 1 1 calc R . . C10 C 0.4673(2) 0.2630(3) 0.1559(2) 0.0195(5) Uani 1 1 d . . . C11 C 0.4112(3) 0.1228(3) 0.1981(2) 0.0207(5) Uani 1 1 d . . . C12 C 0.5370(3) 0.1440(3) 0.2914(2) 0.0221(5) Uani 1 1 d . . . C13 C 0.6880(3) 0.4528(3) 0.3811(2) 0.0218(5) Uani 1 1 d . . . C14 C 0.5644(2) 0.4356(3) 0.2886(2) 0.0192(5) Uani 1 1 d . . . C15 C 0.7413(3) 0.2735(3) 0.1889(2) 0.0213(5) Uani 1 1 d . . . H15 H 0.7518 0.1725 0.1480 0.026 Uiso 1 1 calc R . . C16 C 0.6041(2) 0.2521(3) 0.0863(2) 0.0196(5) Uani 1 1 d . . . H16 H 0.5526 0.1408 -0.0002 0.023 Uiso 1 1 calc R . . C17 C 0.8969(3) 0.4296(3) 0.2093(2) 0.0266(5) Uani 1 1 d . . . C18 C 0.6950(3) 0.3958(3) 0.0531(2) 0.0219(5) Uani 1 1 d . . . C19 C 0.3322(3) 0.2472(3) 0.0561(2) 0.0222(5) Uani 1 1 d . . . H19 H 0.3855 0.3434 0.0348 0.027 Uiso 1 1 calc R . . C20 C 0.1922(3) 0.2526(3) 0.1128(2) 0.0271(5) Uani 1 1 d . . . H20A H 0.1381 0.2872 0.0631 0.041 Uiso 1 1 calc R . . H20B H 0.2376 0.3342 0.2123 0.041 Uiso 1 1 calc R . . H20C H 0.1115 0.1400 0.0992 0.041 Uiso 1 1 calc R . . C21 C 0.2061(3) 0.0984(3) -0.1889(2) 0.0357(6) Uani 1 1 d . . . H21A H 0.1141 0.1152 -0.1783 0.054 Uiso 1 1 calc R . . H21B H 0.1676 -0.0083 -0.2730 0.054 Uiso 1 1 calc R . . H21C H 0.2935 0.1925 -0.1970 0.054 Uiso 1 1 calc R . . O1 O 1.0334(2) 0.4979(2) 0.28256(19) 0.0394(5) Uani 1 1 d . . . O2 O 0.86159(18) 0.49271(19) 0.12776(16) 0.0284(4) Uani 1 1 d . . . O3 O 0.6443(2) 0.4314(2) -0.02372(17) 0.0313(4) Uani 1 1 d . . . O4 O 0.26869(18) 0.09254(18) -0.07118(15) 0.0262(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 0.0248(12) 0.0221(11) 0.0287(12) 0.0123(10) 0.0125(10) 0.0124(10) C2 0.0333(13) 0.0202(12) 0.0396(14) 0.0165(11) 0.0209(11) 0.0113(10) C3 0.0508(16) 0.0277(13) 0.0377(14) 0.0253(12) 0.0258(12) 0.0229(12) C4 0.0384(14) 0.0317(13) 0.0286(13) 0.0205(11) 0.0156(11) 0.0241(11) C5 0.0254(12) 0.0316(13) 0.0220(12) 0.0109(11) 0.0042(10) 0.0136(11) C6 0.0332(13) 0.0227(12) 0.0228(12) 0.0032(10) 0.0033(10) 0.0094(11) C7 0.0346(13) 0.0212(12) 0.0319(13) 0.0107(11) 0.0128(11) 0.0157(11) C8 0.0252(12) 0.0237(11) 0.0248(12) 0.0138(10) 0.0089(9) 0.0148(10) C9 0.0222(11) 0.0249(12) 0.0235(12) 0.0138(10) 0.0052(9) 0.0132(10) C10 0.0200(11) 0.0180(11) 0.0203(11) 0.0100(9) 0.0067(9) 0.0091(9) C11 0.0238(11) 0.0176(11) 0.0229(11) 0.0103(9) 0.0121(9) 0.0115(9) C12 0.0272(12) 0.0225(11) 0.0245(12) 0.0140(10) 0.0126(10) 0.0159(10) C13 0.0222(11) 0.0232(11) 0.0216(11) 0.0131(10) 0.0088(9) 0.0109(9) C14 0.0183(11) 0.0176(11) 0.0201(11) 0.0101(9) 0.0073(9) 0.0073(9) C15 0.0222(11) 0.0198(11) 0.0273(12) 0.0128(10) 0.0098(9) 0.0135(9) C16 0.0227(11) 0.0159(10) 0.0211(11) 0.0092(9) 0.0074(9) 0.0105(9) C17 0.0254(13) 0.0267(12) 0.0298(13) 0.0135(11) 0.0114(10) 0.0149(10) C18 0.0238(12) 0.0219(11) 0.0245(12) 0.0127(10) 0.0100(9) 0.0138(10) C19 0.0226(11) 0.0168(11) 0.0230(11) 0.0083(9) 0.0035(9) 0.0089(9) C20 0.0227(12) 0.0274(12) 0.0301(13) 0.0127(11) 0.0053(10) 0.0139(10) C21 0.0367(14) 0.0374(14) 0.0250(13) 0.0124(11) 0.0005(11) 0.0171(12) O1 0.0213(9) 0.0441(11) 0.0500(11) 0.0264(9) 0.0063(8) 0.0128(8) O2 0.0237(8) 0.0258(9) 0.0373(9) 0.0209(8) 0.0095(7) 0.0094(7) O3 0.0371(10) 0.0354(10) 0.0367(10) 0.0265(8) 0.0155(8) 0.0220(8) O4 0.0287(8) 0.0217(8) 0.0215(8) 0.0071(7) 0.0002(7) 0.0123(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 C1 C2 1.392(3) . ? C1 C11 1.394(3) . ? C2 C3 1.382(3) . ? C3 C4 1.389(3) . ? C4 C12 1.387(3) . ? C5 C6 1.388(3) . ? C5 C13 1.385(3) . ? C6 C7 1.378(3) . ? C7 C8 1.389(3) . ? C8 C14 1.393(3) . ? C9 C12 1.509(3) . ? C9 C13 1.514(3) . ? C9 C15 1.564(3) . ? C10 C11 1.537(3) . ? C10 C14 1.537(3) . ? C10 C16 1.591(3) . ? C10 C19 1.538(3) . ? C11 C12 1.398(3) . ? C13 C14 1.401(3) . ? C15 C16 1.541(3) . ? C15 C17 1.511(3) . ? C16 C18 1.517(3) . ? C17 O1 1.192(3) . ? C17 O2 1.385(3) . ? C18 O2 1.389(3) . ? C18 O3 1.188(3) . ? C19 C20 1.536(3) . ? C19 O4 1.438(2) . ? C21 O4 1.417(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 C2 C1 C11 120.1(2) . . ? C1 C2 C3 120.5(2) . . ? C2 C3 C4 120.0(2) . . ? C3 C4 C12 119.6(2) . . ? C6 C5 C13 119.4(2) . . ? C5 C6 C7 120.1(2) . . ? C6 C7 C8 121.0(2) . . ? C7 C8 C14 119.5(2) . . ? C12 C9 C13 109.15(17) . . ? C12 C9 C15 104.93(17) . . ? C13 C9 C15 105.85(16) . . ? C11 C10 C14 108.56(16) . . ? C11 C10 C16 103.10(15) . . ? C11 C10 C19 116.06(17) . . ? C14 C10 C16 104.05(16) . . ? C14 C10 C19 112.95(17) . . ? C16 C10 C19 111.01(16) . . ? C1 C11 C10 126.91(19) . . ? C1 C11 C12 118.79(19) . . ? C10 C11 C12 114.22(18) . . ? C4 C12 C9 125.3(2) . . ? C4 C12 C11 120.9(2) . . ? C9 C12 C11 113.72(18) . . ? C5 C13 C9 125.2(2) . . ? C5 C13 C14 120.8(2) . . ? C9 C13 C14 113.81(18) . . ? C8 C14 C10 126.63(19) . . ? C8 C14 C13 119.20(19) . . ? C10 C14 C13 113.95(18) . . ? C9 C15 C16 110.15(16) . . ? C9 C15 C17 110.74(17) . . ? C16 C15 C17 104.95(16) . . ? C10 C16 C15 110.47(16) . . ? C10 C16 C18 112.74(16) . . ? C15 C16 C18 103.70(16) . . ? C15 C17 O1 129.3(2) . . ? C15 C17 O2 109.79(18) . . ? O1 C17 O2 120.9(2) . . ? C16 C18 O2 110.25(17) . . ? C16 C18 O3 129.9(2) . . ? O2 C18 O3 119.89(19) . . ? C10 C19 C20 114.98(18) . . ? C10 C19 O4 107.25(16) . . ? C20 C19 O4 110.87(17) . . ? C17 O2 C18 111.28(16) . . ? C19 O4 C21 112.70(17) . . ? 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 C11 C1 C2 C3 -1.2(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C12 1.0(3) . . . . ? C13 C5 C6 C7 -0.7(3) . . . . ? C5 C6 C7 C8 0.7(4) . . . . ? C6 C7 C8 C14 0.7(3) . . . . ? C2 C1 C11 C10 178.4(2) . . . . ? C2 C1 C11 C12 1.7(3) . . . . ? C14 C10 C11 C1 133.1(2) . . . . ? C14 C10 C11 C12 -50.1(2) . . . . ? C16 C10 C11 C1 -116.9(2) . . . . ? C16 C10 C11 C12 59.8(2) . . . . ? C19 C10 C11 C1 4.7(3) . . . . ? C19 C10 C11 C12 -178.59(18) . . . . ? C3 C4 C12 C9 -177.0(2) . . . . ? C3 C4 C12 C11 -0.4(3) . . . . ? C1 C11 C12 C4 -1.0(3) . . . . ? C1 C11 C12 C9 176.04(19) . . . . ? C10 C11 C12 C4 -178.00(19) . . . . ? C10 C11 C12 C9 -1.0(3) . . . . ? C13 C9 C12 C4 -129.9(2) . . . . ? C13 C9 C12 C11 53.2(2) . . . . ? C15 C9 C12 C4 117.0(2) . . . . ? C15 C9 C12 C11 -59.8(2) . . . . ? C6 C5 C13 C9 174.2(2) . . . . ? C6 C5 C13 C14 -0.6(3) . . . . ? C12 C9 C13 C5 131.3(2) . . . . ? C12 C9 C13 C14 -53.5(2) . . . . ? C15 C9 C13 C5 -116.2(2) . . . . ? C15 C9 C13 C14 58.9(2) . . . . ? C7 C8 C14 C10 -176.1(2) . . . . ? C7 C8 C14 C13 -1.9(3) . . . . ? C5 C13 C14 C8 1.9(3) . . . . ? C5 C13 C14 C10 176.80(19) . . . . ? C9 C13 C14 C8 -173.46(18) . . . . ? C9 C13 C14 C10 1.4(2) . . . . ? C11 C10 C14 C8 -135.9(2) . . . . ? C11 C10 C14 C13 49.7(2) . . . . ? C16 C10 C14 C8 114.8(2) . . . . ? C16 C10 C14 C13 -59.6(2) . . . . ? C19 C10 C14 C8 -5.7(3) . . . . ? C19 C10 C14 C13 179.93(17) . . . . ? C12 C9 C15 C16 58.0(2) . . . . ? C12 C9 C15 C17 173.66(17) . . . . ? C13 C9 C15 C16 -57.4(2) . . . . ? C13 C9 C15 C17 58.3(2) . . . . ? C9 C15 C16 C10 0.0(2) . . . . ? C9 C15 C16 C18 121.06(18) . . . . ? C17 C15 C16 C10 -119.22(17) . . . . ? C17 C15 C16 C18 1.8(2) . . . . ? C11 C10 C16 C15 -56.8(2) . . . . ? C11 C10 C16 C18 -172.27(17) . . . . ? C14 C10 C16 C15 56.5(2) . . . . ? C14 C10 C16 C18 -59.0(2) . . . . ? C19 C10 C16 C15 178.30(16) . . . . ? C19 C10 C16 C18 62.8(2) . . . . ? C9 C15 C17 O1 59.0(3) . . . . ? C9 C15 C17 O2 -120.40(19) . . . . ? C16 C15 C17 O1 177.8(2) . . . . ? C16 C15 C17 O2 -1.6(2) . . . . ? C10 C16 C18 O2 117.92(18) . . . . ? C10 C16 C18 O3 -62.5(3) . . . . ? C15 C16 C18 O2 -1.6(2) . . . . ? C15 C16 C18 O3 178.0(2) . . . . ? C11 C10 C19 C20 61.5(2) . . . . ? C11 C10 C19 O4 -62.2(2) . . . . ? C14 C10 C19 C20 -64.8(2) . . . . ? C14 C10 C19 O4 171.45(16) . . . . ? C16 C10 C19 C20 178.81(17) . . . . ? C16 C10 C19 O4 55.0(2) . . . . ? C15 C17 O2 C18 0.6(2) . . . . ? O1 C17 O2 C18 -178.8(2) . . . . ? C16 C18 O2 C17 0.7(2) . . . . ? O3 C18 O2 C17 -179.0(2) . . . . ? C10 C19 O4 C21 -151.95(18) . . . . ? C20 C19 O4 C21 81.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.279 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.044 #===END data_compound7 _database_code_CSD 189243 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 N O3' _chemical_formula_weight 347.40 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 'P 21/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 10.7625(7) _cell_length_b 9.6850(6) _cell_length_c 16.7021(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.067(2) _cell_angle_gamma 90.00 _cell_volume 1738.45(19) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 11489 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 28.78 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.088 _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 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14775 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.78 _reflns_number_total 4136 _reflns_number_gt 3506 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0496P)^2^+1.7203P] 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 4136 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1459 _refine_ls_goodness_of_fit_ref 1.204 _refine_ls_restrained_S_all 1.204 _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 0.39360(17) 0.06692(17) 0.59249(10) 0.0339(4) Uani 1 1 d . . . O2 O 0.14332(14) 0.44486(16) 0.58331(9) 0.0264(4) Uani 1 1 d . . . O3 O 0.27355(13) 0.67859(15) 0.45052(9) 0.0221(3) Uani 1 1 d . . . N1 N 0.25665(16) 0.24622(18) 0.60148(10) 0.0200(4) Uani 1 1 d . . . C1 C 0.44199(18) 0.5525(2) 0.32844(11) 0.0184(4) Uani 1 1 d . . . H1 H 0.3977 0.6374 0.3265 0.022 Uiso 1 1 calc R . . C2 C 0.5524(2) 0.5388(2) 0.28849(12) 0.0235(4) Uani 1 1 d . . . H2 H 0.5822 0.6146 0.2589 0.028 Uiso 1 1 calc R . . C3 C 0.6188(2) 0.4162(2) 0.29156(12) 0.0237(4) Uani 1 1 d . . . H3 H 0.6935 0.4083 0.2640 0.028 Uiso 1 1 calc R . . C4 C 0.57663(18) 0.3048(2) 0.33484(12) 0.0197(4) Uani 1 1 d . . . H4 H 0.6223 0.2209 0.3377 0.024 Uiso 1 1 calc R . . C5 C 0.2286(2) 0.0577(2) 0.37727(13) 0.0235(4) Uani 1 1 d . . . H5 H 0.2785 -0.0233 0.3790 0.028 Uiso 1 1 calc R . . C6 C 0.1020(2) 0.0504(2) 0.35390(14) 0.0302(5) Uani 1 1 d . . . H6 H 0.0663 -0.0355 0.3375 0.036 Uiso 1 1 calc R . . C7 C 0.0287(2) 0.1672(2) 0.35459(14) 0.0276(5) Uani 1 1 d . . . H7 H -0.0578 0.1602 0.3404 0.033 Uiso 1 1 calc R . . C8 C 0.07946(18) 0.2954(2) 0.37572(12) 0.0209(4) Uani 1 1 d . . . H8 H 0.0279 0.3749 0.3769 0.025 Uiso 1 1 calc R . . C9 C 0.27960(17) 0.43617(19) 0.41991(11) 0.0147(4) Uani 1 1 d . . . C10 C 0.41397(18) 0.2073(2) 0.42621(11) 0.0166(4) Uani 1 1 d . . . H10 H 0.4638 0.1201 0.4260 0.020 Uiso 1 1 calc R . . C11 C 0.39744(17) 0.4407(2) 0.37107(11) 0.0157(4) Uani 1 1 d . . . C12 C 0.46626(18) 0.3181(2) 0.37394(11) 0.0166(4) Uani 1 1 d . . . C13 C 0.28008(18) 0.1850(2) 0.39783(11) 0.0171(4) Uani 1 1 d . . . C14 C 0.20714(18) 0.3055(2) 0.39511(11) 0.0168(4) Uani 1 1 d . . . C15 C 0.41409(17) 0.27455(19) 0.51089(11) 0.0157(4) Uani 1 1 d . . . H15 H 0.5011 0.2995 0.5293 0.019 Uiso 1 1 calc R . . C16 C 0.33164(17) 0.40555(19) 0.50843(11) 0.0137(4) Uani 1 1 d . . . H16 H 0.3822 0.4861 0.5288 0.016 Uiso 1 1 calc R . . C17 C 0.35845(19) 0.1806(2) 0.57188(12) 0.0202(4) Uani 1 1 d . . . C18 C 0.23114(18) 0.3740(2) 0.56686(11) 0.0172(4) Uani 1 1 d . . . C19 C 0.1865(2) 0.1887(3) 0.66561(16) 0.0354(6) Uani 1 1 d . . . H19A H 0.2439 0.1449 0.7055 0.053 Uiso 1 1 calc R . . H19B H 0.1276 0.1197 0.6434 0.053 Uiso 1 1 calc R . . H19C H 0.1408 0.2627 0.6912 0.053 Uiso 1 1 calc R . . C20 C 0.19953(18) 0.5676(2) 0.41614(12) 0.0175(4) Uani 1 1 d . . . H20 H 0.1273 0.5528 0.4504 0.021 Uiso 1 1 calc R . . C21 C 0.1480(2) 0.6087(2) 0.33171(13) 0.0252(5) Uani 1 1 d . . . H21A H 0.2047 0.5760 0.2918 0.038 Uiso 1 1 calc R . . H21B H 0.1407 0.7094 0.3284 0.038 Uiso 1 1 calc R . . H21C H 0.0659 0.5668 0.3213 0.038 Uiso 1 1 calc R . . C22 C 0.2054(2) 0.7649(2) 0.50140(14) 0.0286(5) Uani 1 1 d . . . H22A H 0.1797 0.7113 0.5475 0.043 Uiso 1 1 calc R . . H22B H 0.1315 0.8007 0.4714 0.043 Uiso 1 1 calc R . . H22C H 0.2580 0.8421 0.5203 0.043 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 0.0447(10) 0.0253(8) 0.0329(9) 0.0110(7) 0.0130(7) 0.0129(7) O2 0.0226(8) 0.0300(8) 0.0275(8) 0.0042(6) 0.0103(6) 0.0079(6) O3 0.0218(7) 0.0175(7) 0.0273(8) -0.0032(6) 0.0037(6) 0.0001(6) N1 0.0203(8) 0.0201(8) 0.0201(8) 0.0032(7) 0.0064(7) -0.0011(7) C1 0.0191(9) 0.0217(10) 0.0144(9) 0.0023(7) -0.0004(7) -0.0003(8) C2 0.0235(10) 0.0302(11) 0.0171(10) 0.0047(8) 0.0032(8) -0.0068(9) C3 0.0189(10) 0.0357(12) 0.0170(10) -0.0009(8) 0.0055(8) -0.0009(9) C4 0.0156(9) 0.0255(10) 0.0181(9) -0.0031(8) 0.0023(7) 0.0027(8) C5 0.0266(11) 0.0214(10) 0.0233(10) -0.0037(8) 0.0086(8) -0.0036(8) C6 0.0309(12) 0.0287(12) 0.0316(12) -0.0109(9) 0.0066(9) -0.0129(10) C7 0.0183(10) 0.0376(13) 0.0270(11) -0.0088(10) 0.0019(8) -0.0099(9) C8 0.0160(9) 0.0288(11) 0.0182(9) -0.0026(8) 0.0036(7) -0.0017(8) C9 0.0136(8) 0.0163(9) 0.0144(8) 0.0006(7) 0.0018(7) 0.0020(7) C10 0.0166(9) 0.0154(9) 0.0182(9) -0.0014(7) 0.0038(7) 0.0019(7) C11 0.0144(9) 0.0202(9) 0.0126(8) -0.0016(7) 0.0012(7) -0.0016(7) C12 0.0167(9) 0.0199(9) 0.0133(9) -0.0020(7) 0.0007(7) -0.0017(7) C13 0.0178(9) 0.0200(9) 0.0140(9) -0.0015(7) 0.0054(7) -0.0019(7) C14 0.0177(9) 0.0215(9) 0.0116(8) -0.0016(7) 0.0037(7) -0.0026(8) C15 0.0139(8) 0.0169(9) 0.0164(9) -0.0003(7) 0.0006(7) 0.0018(7) C16 0.0123(8) 0.0149(8) 0.0141(8) 0.0006(7) 0.0019(7) 0.0009(7) C17 0.0226(10) 0.0208(10) 0.0170(9) 0.0008(7) 0.0008(8) 0.0013(8) C18 0.0174(9) 0.0188(9) 0.0154(9) -0.0011(7) 0.0017(7) -0.0005(7) C19 0.0368(13) 0.0335(13) 0.0380(14) 0.0119(11) 0.0205(11) 0.0005(11) C20 0.0147(9) 0.0174(9) 0.0203(9) 0.0013(7) 0.0019(7) 0.0013(7) C21 0.0224(10) 0.0274(11) 0.0252(11) 0.0046(9) -0.0036(8) 0.0054(9) C22 0.0345(12) 0.0222(11) 0.0295(12) -0.0033(9) 0.0058(9) 0.0053(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 C17 1.209(3) . ? O2 C18 1.212(2) . ? O3 C20 1.439(2) . ? O3 C22 1.423(3) . ? N1 C17 1.381(3) . ? N1 C18 1.387(3) . ? N1 C19 1.454(3) . ? C1 C2 1.400(3) . ? C1 C11 1.395(3) . ? C2 C3 1.385(3) . ? C3 C4 1.388(3) . ? C4 C12 1.392(3) . ? C5 C6 1.399(3) . ? C5 C13 1.388(3) . ? C6 C7 1.380(3) . ? C7 C8 1.394(3) . ? C8 C14 1.398(3) . ? C9 C11 1.545(3) . ? C9 C14 1.532(3) . ? C9 C16 1.581(3) . ? C9 C20 1.537(3) . ? C10 C12 1.511(3) . ? C10 C13 1.508(3) . ? C10 C15 1.557(3) . ? C11 C12 1.399(3) . ? C13 C14 1.405(3) . ? C15 C16 1.548(3) . ? C15 C17 1.513(3) . ? C16 C18 1.526(3) . ? C20 C21 1.540(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 C20 O3 C22 112.63(16) . . ? C17 N1 C18 113.84(16) . . ? C17 N1 C19 122.74(18) . . ? C18 N1 C19 123.37(18) . . ? C2 C1 C11 119.54(19) . . ? C1 C2 C3 120.87(19) . . ? C2 C3 C4 120.18(19) . . ? C3 C4 C12 118.93(19) . . ? C6 C5 C13 118.9(2) . . ? C5 C6 C7 120.3(2) . . ? C6 C7 C8 121.0(2) . . ? C7 C8 C14 119.2(2) . . ? C11 C9 C14 107.51(15) . . ? C11 C9 C16 103.84(14) . . ? C11 C9 C20 115.43(15) . . ? C14 C9 C16 104.34(14) . . ? C14 C9 C20 113.40(15) . . ? C16 C9 C20 111.32(15) . . ? C12 C10 C13 107.41(15) . . ? C12 C10 C15 104.22(15) . . ? C13 C10 C15 107.44(15) . . ? C1 C11 C9 127.27(17) . . ? C1 C11 C12 118.72(17) . . ? C9 C11 C12 113.97(16) . . ? C4 C12 C10 124.00(18) . . ? C4 C12 C11 121.74(18) . . ? C10 C12 C11 114.17(16) . . ? C5 C13 C10 124.53(18) . . ? C5 C13 C14 120.99(18) . . ? C10 C13 C14 114.46(17) . . ? C8 C14 C9 126.88(18) . . ? C8 C14 C13 119.32(18) . . ? C9 C14 C13 113.68(16) . . ? C10 C15 C16 110.26(15) . . ? C10 C15 C17 112.27(16) . . ? C16 C15 C17 105.29(15) . . ? C9 C16 C15 110.65(14) . . ? C9 C16 C18 114.07(15) . . ? C15 C16 C18 104.11(15) . . ? O1 C17 N1 124.0(2) . . ? O1 C17 C15 127.63(19) . . ? N1 C17 C15 108.35(17) . . ? O2 C18 N1 123.39(18) . . ? O2 C18 C16 128.29(18) . . ? N1 C18 C16 108.31(16) . . ? O3 C20 C9 107.77(15) . . ? O3 C20 C21 109.70(16) . . ? C9 C20 C21 115.17(16) . . ? 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 C11 C1 C2 C3 -0.8(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C12 0.8(3) . . . . ? C13 C5 C6 C7 -2.7(3) . . . . ? C5 C6 C7 C8 2.3(3) . . . . ? C6 C7 C8 C14 1.1(3) . . . . ? C2 C1 C11 C9 178.83(18) . . . . ? C2 C1 C11 C12 1.2(3) . . . . ? C14 C9 C11 C1 131.72(19) . . . . ? C14 C9 C11 C12 -50.6(2) . . . . ? C16 C9 C11 C1 -118.1(2) . . . . ? C16 C9 C11 C12 59.61(19) . . . . ? C20 C9 C11 C1 4.0(3) . . . . ? C20 C9 C11 C12 -178.26(16) . . . . ? C3 C4 C12 C10 -176.81(18) . . . . ? C3 C4 C12 C11 -0.3(3) . . . . ? C1 C11 C12 C4 -0.7(3) . . . . ? C1 C11 C12 C10 176.11(17) . . . . ? C9 C11 C12 C4 -178.58(17) . . . . ? C9 C11 C12 C10 -1.8(2) . . . . ? C13 C10 C12 C4 -128.94(19) . . . . ? C13 C10 C12 C11 54.4(2) . . . . ? C15 C10 C12 C4 117.27(19) . . . . ? C15 C10 C12 C11 -59.4(2) . . . . ? C6 C5 C13 C10 178.23(19) . . . . ? C6 C5 C13 C14 -0.3(3) . . . . ? C12 C10 C13 C5 127.2(2) . . . . ? C12 C10 C13 C14 -54.3(2) . . . . ? C15 C10 C13 C5 -121.2(2) . . . . ? C15 C10 C13 C14 57.3(2) . . . . ? C7 C8 C14 C9 -179.79(19) . . . . ? C7 C8 C14 C13 -4.0(3) . . . . ? C5 C13 C14 C8 3.6(3) . . . . ? C5 C13 C14 C9 179.92(18) . . . . ? C10 C13 C14 C8 -175.03(17) . . . . ? C10 C13 C14 C9 1.3(2) . . . . ? C11 C9 C14 C8 -133.3(2) . . . . ? C11 C9 C14 C13 50.7(2) . . . . ? C16 C9 C14 C8 116.8(2) . . . . ? C16 C9 C14 C13 -59.17(19) . . . . ? C20 C9 C14 C8 -4.5(3) . . . . ? C20 C9 C14 C13 179.52(16) . . . . ? C12 C10 C15 C16 60.21(19) . . . . ? C12 C10 C15 C17 177.27(15) . . . . ? C13 C10 C15 C16 -53.6(2) . . . . ? C13 C10 C15 C17 63.5(2) . . . . ? C10 C15 C16 C9 -3.6(2) . . . . ? C10 C15 C16 C18 119.39(16) . . . . ? C17 C15 C16 C9 -124.89(16) . . . . ? C17 C15 C16 C18 -1.93(19) . . . . ? C11 C9 C16 C15 -54.08(18) . . . . ? C11 C9 C16 C18 -171.06(15) . . . . ? C14 C9 C16 C15 58.43(18) . . . . ? C14 C9 C16 C18 -58.54(19) . . . . ? C20 C9 C16 C15 -178.90(15) . . . . ? C20 C9 C16 C18 64.1(2) . . . . ? C18 N1 C17 O1 -177.7(2) . . . . ? C18 N1 C17 C15 1.9(2) . . . . ? C19 N1 C17 O1 4.9(3) . . . . ? C19 N1 C17 C15 -175.5(2) . . . . ? C10 C15 C17 O1 59.8(3) . . . . ? C10 C15 C17 N1 -119.78(18) . . . . ? C16 C15 C17 O1 179.8(2) . . . . ? C16 C15 C17 N1 0.2(2) . . . . ? C17 N1 C18 O2 177.66(19) . . . . ? C17 N1 C18 C16 -3.2(2) . . . . ? C19 N1 C18 O2 -5.0(3) . . . . ? C19 N1 C18 C16 174.2(2) . . . . ? C9 C16 C18 O2 -57.2(3) . . . . ? C9 C16 C18 N1 123.74(17) . . . . ? C15 C16 C18 O2 -177.9(2) . . . . ? C15 C16 C18 N1 3.0(2) . . . . ? C22 O3 C20 C9 -137.74(17) . . . . ? C22 O3 C20 C21 96.2(2) . . . . ? C11 C9 C20 O3 -62.7(2) . . . . ? C11 C9 C20 C21 60.1(2) . . . . ? C14 C9 C20 O3 172.59(15) . . . . ? C14 C9 C20 C21 -64.6(2) . . . . ? C16 C9 C20 O3 55.30(19) . . . . ? C16 C9 C20 C21 178.10(16) . . . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.465 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.060