data_global _journal_coden_Cambridge 207 #--------------------------------------------------------------------------- #-- _publ_requested_journal 'Perkin Transactions 1 ' _publ_contact_author 'Dr T Donohoe' _publ_contact_author_address ; Dr T Donohoe Department of Chemistry The University of Manchester Oxford Road Manchester M13 9PL UK ; _publ_contact_letter ; ENTER TEXT OF LETTER ; loop_ _publ_author_name 'Donohoe, T.' 'Helliwell, Madeleine' 'McRiner, Andrew J.' 'Sheldrake, Peter' _publ_section_title ; ENTER SECTION TITLE ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; The structure was solved by direct methods. C10 was disordered over two sites, A and B, whose occupancies were constrained to sum to 1.0. Non-H atoms, except C10A and C10B, were refined anisotropically and H atoms were included in constrained positions. ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Sheldrick, G.M. (1985). In: "Crystallographic Computing 3" (Eds G.M. Sheldrick, C. Kruger and R. Goddard) Oxford University Press, pp. 175-189. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; data_compound_11 _database_code_CSD 159038 _audit_creation_date '19100-04-05' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H23 N O4' _chemical_formula_weight 281.34 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 'C 2/c ' _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall ? 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 25.365(11) _cell_length_b 11.860(5) _cell_length_c 12.158(6) _cell_angle_alpha 90.00 _cell_angle_beta 116.14(4) _cell_angle_gamma 90.00 _cell_volume 3284(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 14.8 _cell_measurement_theta_max 16.7 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.671 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.846 _exptl_special_details ; The scan width was (1.31+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #--------------------------------------------------------------------------- #-- _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -2.55 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 0 4 2 4 1 -7 1 -1 _diffrn_reflns_number 2953 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 70.10 _reflns_number_total 2886 _reflns_number_gt 1898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SHELXS86 (Sheldrick, 1985) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'teXsan (MSC, 1995)' _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 w=1/[\s^2^(Fo^2^)+(0.1447P)^2^+2.4372P] 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 SHELXL _refine_ls_extinction_coef 0.0007(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2886 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1106 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.2549 _refine_ls_wR_factor_gt 0.2223 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.005 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.65050(11) 0.3800(2) 0.7258(3) 0.0890(8) Uani 1 d . . . O2 O 0.66349(14) 0.1924(3) 0.7238(3) 0.1143(11) Uani 1 d . . . O3 O 0.40388(12) 0.1903(2) 0.2899(2) 0.0858(8) Uani 1 d . . . O4 O 0.44902(13) 0.3579(2) 0.3315(2) 0.0877(9) Uani 1 d . . . N1 N 0.47228(11) 0.3499(2) 0.5723(2) 0.0595(7) Uani 1 d . . . C1 C 0.53120(14) 0.3557(3) 0.6264(3) 0.0585(8) Uani 1 d . . . H1 H 0.5486 0.4253 0.6559 0.070 Uiso 1 calc R . . C2 C 0.56707(15) 0.2655(3) 0.6408(3) 0.0649(8) Uani 1 d . . . C3 C 0.53882(19) 0.1568(3) 0.6063(3) 0.0768(10) Uani 1 d . . . H3 H 0.5616 0.0917 0.6289 0.092 Uiso 1 calc R . . C4 C 0.48140(19) 0.1484(3) 0.5435(3) 0.0776(10) Uani 1 d . . . H4 H 0.4644 0.0771 0.5277 0.093 Uiso 1 calc R . . C5 C 0.44199(15) 0.2510(3) 0.4958(3) 0.0642(8) Uani 1 d . . . C6 C 0.38255(18) 0.2294(4) 0.4974(4) 0.0858(12) Uani 1 d . . . H6A H 0.3885 0.2194 0.5805 0.129 Uiso 1 calc R . . H6B H 0.3650 0.1627 0.4510 0.129 Uiso 1 calc R . . H6C H 0.3571 0.2927 0.4619 0.129 Uiso 1 calc R . . C7 C 0.43700(15) 0.4497(3) 0.5668(3) 0.0685(9) Uani 1 d . . . H7A H 0.4116 0.4327 0.6043 0.103 Uiso 1 calc R . . H7B H 0.4138 0.4707 0.4829 0.103 Uiso 1 calc R . . H7C H 0.4625 0.5109 0.6098 0.103 Uiso 1 calc R . . C8 C 0.63060(17) 0.2734(3) 0.7004(3) 0.0757(9) Uani 1 d . . . C9 C 0.71405(17) 0.3967(4) 0.7891(4) 0.0953(13) Uani 1 d . . . H9 H 0.7341 0.3307 0.7767 0.114 Uiso 1 calc R . . C10 C 0.7304(2) 0.4104(6) 0.9197(5) 0.140(2) Uani 1 d . . . H10A H 0.7716 0.4267 0.9627 0.209 Uiso 1 calc R . . H10B H 0.7220 0.3421 0.9513 0.209 Uiso 1 calc R . . H10C H 0.7084 0.4714 0.9309 0.209 Uiso 1 calc R . . C11 C 0.72714(18) 0.4980(5) 0.7326(4) 0.190(4) Uani 1 d . . . H11A H 0.7064 0.5620 0.7425 0.286 Uiso 1 calc R . . H11B H 0.7148 0.4845 0.6469 0.286 Uiso 1 calc R . . H11C H 0.7686 0.5127 0.7720 0.286 Uiso 1 calc R . . C12 C 0.43217(11) 0.2758(2) 0.3635(2) 0.0649(9) Uani 1 d R . . C13 C 0.39326(13) 0.1959(2) 0.1611(2) 0.0869(11) Uani 1 d R . . H13 H 0.4270 0.2361 0.1609 0.104 Uiso 1 calc R A 1 C14 C 0.3965(4) 0.0804(5) 0.1211(5) 0.161(3) Uani 1 d . . . H14A H 0.3711 0.0323 0.1397 0.242 Uiso 1 calc R . . H14B H 0.4362 0.0535 0.1630 0.242 Uiso 1 calc R . . H14C H 0.3845 0.0799 0.0343 0.242 Uiso 1 calc R . . C15A C 0.3433(4) 0.2620(8) 0.0894(8) 0.124(3) Uiso 0.66 d P B 1 H15A H 0.3110 0.2399 0.1058 0.186 Uiso 0.66 calc PR B 1 H15B H 0.3329 0.2508 0.0041 0.186 Uiso 0.66 calc PR B 1 H15C H 0.3520 0.3402 0.1096 0.186 Uiso 0.66 calc PR B 1 C15B C 0.3190(9) 0.1813(18) 0.093(2) 0.152(7) Uiso 0.34 d P B 2 H15D H 0.3065 0.1520 0.1517 0.228 Uiso 0.34 calc PR B 2 H15E H 0.3075 0.1301 0.0254 0.228 Uiso 0.34 calc PR B 2 H15F H 0.3010 0.2534 0.0644 0.228 Uiso 0.34 calc PR B 2 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 0.0637(15) 0.0893(18) 0.1057(19) -0.0106(15) 0.0297(13) -0.0045(13) O2 0.096(2) 0.094(2) 0.143(3) 0.0035(19) 0.044(2) 0.0272(17) O3 0.120(2) 0.0703(15) 0.0615(14) -0.0164(11) 0.0351(14) -0.0314(14) O4 0.131(2) 0.0711(15) 0.0725(15) -0.0113(12) 0.0551(16) -0.0357(15) N1 0.0697(17) 0.0534(14) 0.0557(14) -0.0087(11) 0.0280(12) -0.0065(11) C1 0.070(2) 0.0579(17) 0.0478(15) -0.0060(13) 0.0259(14) -0.0112(14) C2 0.077(2) 0.0603(18) 0.0582(18) -0.0036(14) 0.0311(16) -0.0004(15) C3 0.098(3) 0.0582(19) 0.067(2) 0.0006(16) 0.030(2) 0.0060(18) C4 0.103(3) 0.0477(17) 0.078(2) -0.0043(16) 0.036(2) -0.0139(17) C5 0.077(2) 0.0589(17) 0.0592(17) -0.0086(14) 0.0328(16) -0.0175(15) C6 0.094(3) 0.092(3) 0.082(2) -0.018(2) 0.048(2) -0.035(2) C7 0.075(2) 0.0661(19) 0.0658(19) -0.0066(15) 0.0329(16) -0.0008(16) C8 0.076(2) 0.083(2) 0.069(2) 0.0004(18) 0.0326(17) 0.0064(19) C9 0.064(2) 0.119(3) 0.100(3) -0.010(3) 0.034(2) -0.007(2) C10 0.085(3) 0.204(7) 0.119(4) -0.011(4) 0.035(3) -0.008(4) C11 0.118(5) 0.267(9) 0.168(6) 0.051(6) 0.047(4) -0.071(6) C12 0.077(2) 0.0573(17) 0.0604(18) -0.0115(14) 0.0303(16) -0.0143(15) C13 0.110(3) 0.082(2) 0.059(2) -0.0141(18) 0.029(2) -0.012(2) C14 0.254(8) 0.127(5) 0.102(4) -0.018(3) 0.078(5) 0.036(5) _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 C8 1.345(5) . ? O1 C9 1.462(5) . ? O2 C8 1.221(4) . ? O3 C12 1.334(3) . ? O3 C13 1.468(3) . ? O4 C12 1.195(3) . ? N1 C1 1.343(4) . ? N1 C7 1.467(4) . ? N1 C5 1.484(4) . ? C1 C2 1.365(4) . ? C1 H1 0.9300 . ? C2 C3 1.444(5) . ? C2 C8 1.450(5) . ? C3 C4 1.317(6) . ? C3 H3 0.9300 . ? C4 C5 1.518(5) . ? C4 H4 0.9300 . ? C5 C6 1.538(5) . ? C5 C12 1.545(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 C10 1.463(7) . ? C9 C11 1.492(5) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C13 C15A 1.417(9) . ? C13 C14 1.469(6) . ? C13 C15B 1.70(2) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15A H15A 0.9600 . ? C15A H15B 0.9600 . ? C15A H15C 0.9600 . ? C15B H15D 0.9600 . ? C15B H15E 0.9600 . ? C15B H15F 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 C8 O1 C9 117.6(3) . . ? C12 O3 C13 118.1(2) . . ? C1 N1 C7 120.4(3) . . ? C1 N1 C5 120.3(3) . . ? C7 N1 C5 118.2(3) . . ? N1 C1 C2 123.9(3) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 116.4(3) . . ? C1 C2 C8 123.0(3) . . ? C3 C2 C8 120.2(3) . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 122.3(3) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? N1 C5 C4 108.8(3) . . ? N1 C5 C6 111.3(3) . . ? C4 C5 C6 110.3(3) . . ? N1 C5 C12 107.6(2) . . ? C4 C5 C12 109.1(3) . . ? C6 C5 C12 109.6(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 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 O1 122.5(4) . . ? O2 C8 C2 124.1(4) . . ? O1 C8 C2 113.4(3) . . ? O1 C9 C10 107.8(4) . . ? O1 C9 C11 106.5(3) . . ? C10 C9 C11 113.3(5) . . ? O1 C9 H9 109.7 . . ? C10 C9 H9 109.7 . . ? C11 C9 H9 109.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O4 C12 O3 124.4(3) . . ? O4 C12 C5 125.3(2) . . ? O3 C12 C5 110.2(2) . . ? C15A C13 C14 118.5(5) . . ? C15A C13 O3 112.1(4) . . ? C14 C13 O3 107.5(3) . . ? C15A C13 C15B 42.1(7) . . ? C14 C13 C15B 87.5(8) . . ? O3 C13 C15B 99.0(7) . . ? C15A C13 H13 106.0 . . ? C14 C13 H13 105.9 . . ? O3 C13 H13 105.9 . . ? C15B C13 H13 146.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15A H15A 109.5 . . ? C13 C15A H15B 109.5 . . ? C13 C15A H15C 109.5 . . ? C13 C15B H15D 109.5 . . ? C13 C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C13 C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 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 C7 N1 C1 C2 176.5(3) . . . . ? C5 N1 C1 C2 -15.9(4) . . . . ? N1 C1 C2 C3 -6.6(4) . . . . ? N1 C1 C2 C8 -179.5(3) . . . . ? C1 C2 C3 C4 12.4(5) . . . . ? C8 C2 C3 C4 -174.5(3) . . . . ? C2 C3 C4 C5 4.4(6) . . . . ? C1 N1 C5 C4 29.4(4) . . . . ? C7 N1 C5 C4 -162.8(3) . . . . ? C1 N1 C5 C6 151.1(3) . . . . ? C7 N1 C5 C6 -41.1(4) . . . . ? C1 N1 C5 C12 -88.7(3) . . . . ? C7 N1 C5 C12 79.1(3) . . . . ? C3 C4 C5 N1 -24.0(5) . . . . ? C3 C4 C5 C6 -146.3(4) . . . . ? C3 C4 C5 C12 93.2(4) . . . . ? C9 O1 C8 O2 -3.0(6) . . . . ? C9 O1 C8 C2 178.4(3) . . . . ? C1 C2 C8 O2 173.3(4) . . . . ? C3 C2 C8 O2 0.7(6) . . . . ? C1 C2 C8 O1 -8.1(5) . . . . ? C3 C2 C8 O1 179.4(3) . . . . ? C8 O1 C9 C10 -97.5(5) . . . . ? C8 O1 C9 C11 140.5(4) . . . . ? C13 O3 C12 O4 0.9(5) . . . . ? C13 O3 C12 C5 -176.9(2) . . . . ? N1 C5 C12 O4 3.6(4) . . . . ? C4 C5 C12 O4 -114.3(4) . . . . ? C6 C5 C12 O4 124.8(3) . . . . ? N1 C5 C12 O3 -178.7(3) . . . . ? C4 C5 C12 O3 63.4(3) . . . . ? C6 C5 C12 O3 -57.5(3) . . . . ? C12 O3 C13 C15A -81.9(5) . . . . ? C12 O3 C13 C14 146.1(4) . . . . ? C12 O3 C13 C15B -123.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.439 _diffrn_reflns_theta_full 70.10 _diffrn_measured_fraction_theta_full 0.439 _refine_diff_density_max 0.425 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.046 data_compound_23 _database_code_CSD 159039 #--------------------------------------------------------------------------- _audit_creation_date '19100-05-31' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H23 N O4' _chemical_formula_weight 293.35 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' '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 triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' _cell_length_a 9.886(5) _cell_length_b 12.422(5) _cell_length_c 7.391(2) _cell_angle_alpha 93.16(3) _cell_angle_beta 95.88(3) _cell_angle_gamma 111.93(3) _cell_volume 833.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 7.0 _cell_measurement_theta_max 9.6 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.933 _exptl_special_details ; The scan width was (1.15+0.30tan\q)\% with an \w scan speed of 8\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #--------------------------------------------------------------------------- #-- _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -2.58 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 2 -1 2 -3 -2 3 -2 -2 _diffrn_reflns_number 3122 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.1117 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2937 _reflns_number_gt 1252 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SHELXS86 (Sheldrick, 1985) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'teXsan (MSC, 1995)' _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 w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.3567P] 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_number_reflns 2937 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2236 _refine_ls_R_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.2176 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7633(4) -0.3031(3) 0.1723(5) 0.0762(11) Uani 1 d . . . O2 O 0.5554(5) -0.3039(4) 0.0144(5) 0.0991(14) Uani 1 d . . . O3 O 0.6995(4) 0.1815(3) 0.3926(4) 0.0762(11) Uani 1 d . . . O4 O 0.8362(4) 0.1004(3) 0.5457(5) 0.0847(12) Uani 1 d . . . N1 N 0.9432(4) 0.0503(4) 0.2408(5) 0.0548(10) Uani 1 d . . . C1 C 0.8844(5) -0.0655(5) 0.2099(6) 0.0537(12) Uani 1 d . . . H1 H 0.9412 -0.1075 0.2465 0.064 Uiso 1 calc R . . C2 C 0.7445(5) -0.1247(5) 0.1269(6) 0.0550(12) Uani 1 d . . . C3 C 0.6701(6) -0.0552(5) 0.0452(7) 0.0695(15) Uani 1 d . . . H3 H 0.5830 -0.0923 -0.0338 0.083 Uiso 1 calc R . . C4 C 0.7216(6) 0.0586(6) 0.0794(7) 0.0731(16) Uani 1 d . . . H4 H 0.6781 0.1017 0.0140 0.088 Uiso 1 calc R . . C5 C 0.8512(5) 0.1196(4) 0.2243(6) 0.0553(13) Uani 1 d . . . C6 C 0.9622(6) 0.2370(5) 0.1849(7) 0.0809(17) Uani 1 d . . . H6A H 0.9705 0.2385 0.0553 0.097 Uiso 1 calc R . . H6B H 0.9339 0.3003 0.2252 0.097 Uiso 1 calc R . . C7 C 1.1046(6) 0.2462(5) 0.2930(8) 0.0870(17) Uani 1 d . . . H7A H 1.1878 0.2927 0.2348 0.104 Uiso 1 calc R . . H7B H 1.1146 0.2822 0.4161 0.104 Uiso 1 calc R . . C8 C 1.0973(5) 0.1231(4) 0.2970(6) 0.0648(14) Uani 1 d . . . H8A H 1.1585 0.1073 0.2131 0.078 Uiso 1 calc R . . H8B H 1.1296 0.1096 0.4190 0.078 Uiso 1 calc R . . C9 C 0.6766(7) -0.2500(5) 0.0966(7) 0.0734(16) Uani 1 d . . . C10 C 0.6990(7) -0.4299(5) 0.1556(8) 0.0840(17) Uani 1 d . . . H10 H 0.6393 -0.4591 0.0359 0.101 Uiso 1 calc R . . C11 C 0.8261(8) -0.4678(5) 0.1688(11) 0.130(3) Uani 1 d . . . H11A H 0.8759 -0.4485 0.0631 0.195 Uiso 1 calc R . . H11B H 0.7909 -0.5506 0.1746 0.195 Uiso 1 calc R . . H11C H 0.8930 -0.4288 0.2769 0.195 Uiso 1 calc R . . C12 C 0.6041(8) -0.4682(5) 0.3029(9) 0.119(2) Uani 1 d . . . H12A H 0.6635 -0.4423 0.4201 0.178 Uiso 1 calc R . . H12B H 0.5576 -0.5518 0.2899 0.178 Uiso 1 calc R . . H12C H 0.5303 -0.4353 0.2937 0.178 Uiso 1 calc R . . C13 C 0.7984(5) 0.1328(4) 0.4085(7) 0.0624(14) Uani 1 d . . . C14 C 0.6288(6) 0.1935(5) 0.5528(7) 0.0778(17) Uani 1 d . . . H14 H 0.6195 0.1284 0.6262 0.093 Uiso 1 calc R . . C15 C 0.7207(7) 0.3060(6) 0.6649(9) 0.126(3) Uani 1 d . . . H15A H 0.7360 0.3693 0.5903 0.188 Uiso 1 calc R . . H15B H 0.8140 0.3040 0.7112 0.188 Uiso 1 calc R . . H15C H 0.6712 0.3170 0.7653 0.188 Uiso 1 calc R . . C16 C 0.4790(6) 0.1866(5) 0.4783(8) 0.100(2) Uani 1 d . . . H16A H 0.4268 0.1944 0.5776 0.150 Uiso 1 calc R . . H16B H 0.4259 0.1126 0.4079 0.150 Uiso 1 calc R . . H16C H 0.4880 0.2482 0.4017 0.150 Uiso 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 0.078(3) 0.060(3) 0.084(3) 0.0019(19) 0.002(2) 0.021(2) O2 0.080(3) 0.103(3) 0.093(3) -0.018(2) -0.019(2) 0.022(3) O3 0.090(3) 0.105(3) 0.068(2) 0.025(2) 0.028(2) 0.069(2) O4 0.107(3) 0.127(3) 0.055(2) 0.023(2) 0.015(2) 0.082(3) N1 0.050(3) 0.064(3) 0.056(3) 0.006(2) 0.002(2) 0.029(2) C1 0.064(4) 0.072(4) 0.039(3) 0.010(2) 0.018(3) 0.038(3) C2 0.050(3) 0.073(4) 0.041(3) -0.001(2) 0.004(2) 0.025(3) C3 0.061(3) 0.097(4) 0.058(3) 0.001(3) -0.001(3) 0.042(4) C4 0.082(4) 0.106(5) 0.054(3) 0.019(3) 0.008(3) 0.061(4) C5 0.057(3) 0.072(3) 0.051(3) 0.014(3) 0.011(3) 0.038(3) C6 0.083(4) 0.087(4) 0.091(4) 0.035(3) 0.033(3) 0.045(4) C7 0.079(4) 0.072(4) 0.111(5) 0.008(3) 0.024(4) 0.028(3) C8 0.061(4) 0.083(4) 0.056(3) 0.010(3) 0.011(3) 0.033(3) C9 0.081(4) 0.086(5) 0.058(4) -0.001(3) 0.009(3) 0.038(4) C10 0.097(5) 0.070(4) 0.072(4) 0.001(3) 0.011(4) 0.019(4) C11 0.119(6) 0.074(4) 0.199(8) 0.004(5) 0.010(5) 0.043(4) C12 0.148(6) 0.086(5) 0.100(5) 0.008(4) 0.026(5) 0.018(4) C13 0.065(3) 0.076(4) 0.063(4) 0.014(3) 0.014(3) 0.044(3) C14 0.087(4) 0.105(5) 0.069(4) 0.016(3) 0.029(3) 0.062(4) C15 0.099(5) 0.150(7) 0.121(6) -0.035(5) -0.009(4) 0.052(5) C16 0.083(4) 0.137(6) 0.097(5) 0.003(4) 0.026(4) 0.059(4) _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 C9 1.360(6) . ? O1 C10 1.454(6) . ? O2 C9 1.208(6) . ? O3 C13 1.327(5) . ? O3 C14 1.463(5) . ? O4 C13 1.187(5) . ? N1 C1 1.331(5) . ? N1 C8 1.453(6) . ? N1 C5 1.469(5) . ? C1 C2 1.359(6) . ? C1 H1 0.9300 . ? C2 C9 1.441(7) . ? C2 C3 1.446(6) . ? C3 C4 1.310(7) . ? C3 H3 0.9300 . ? C4 C5 1.505(7) . ? C4 H4 0.9300 . ? C5 C6 1.527(6) . ? C5 C13 1.529(6) . ? C6 C7 1.508(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.506(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C12 1.492(7) . ? C10 C11 1.494(7) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C14 C15 1.495(8) . ? C14 C16 1.495(7) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 C9 O1 C10 115.9(5) . . ? C13 O3 C14 118.2(4) . . ? C1 N1 C8 126.9(4) . . ? C1 N1 C5 121.2(4) . . ? C8 N1 C5 111.9(4) . . ? N1 C1 C2 122.5(4) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C9 123.7(5) . . ? C1 C2 C3 116.3(5) . . ? C9 C2 C3 119.5(5) . . ? C4 C3 C2 121.9(5) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 120.2(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 109.2(4) . . ? N1 C5 C6 101.5(4) . . ? C4 C5 C6 116.8(4) . . ? N1 C5 C13 108.9(4) . . ? C4 C5 C13 110.2(4) . . ? C6 C5 C13 109.8(4) . . ? C7 C6 C5 103.9(4) . . ? C7 C6 H6A 111.0 . . ? C5 C6 H6A 111.0 . . ? C7 C6 H6B 111.0 . . ? C5 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? C8 C7 C6 105.9(4) . . ? C8 C7 H7A 110.5 . . ? C6 C7 H7A 110.5 . . ? C8 C7 H7B 110.5 . . ? C6 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? N1 C8 C7 104.7(4) . . ? N1 C8 H8A 110.8 . . ? C7 C8 H8A 110.8 . . ? N1 C8 H8B 110.8 . . ? C7 C8 H8B 110.8 . . ? H8A C8 H8B 108.9 . . ? O2 C9 O1 122.7(6) . . ? O2 C9 C2 124.6(5) . . ? O1 C9 C2 112.8(5) . . ? O1 C10 C12 108.8(5) . . ? O1 C10 C11 105.6(5) . . ? C12 C10 C11 113.5(6) . . ? O1 C10 H10 109.6 . . ? C12 C10 H10 109.6 . . ? C11 C10 H10 109.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O4 C13 O3 124.4(5) . . ? O4 C13 C5 125.0(4) . . ? O3 C13 C5 110.5(4) . . ? O3 C14 C15 109.2(5) . . ? O3 C14 C16 105.4(4) . . ? C15 C14 C16 113.7(5) . . ? O3 C14 H14 109.5 . . ? C15 C14 H14 109.5 . . ? C16 C14 H14 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C8 N1 C1 C2 -167.9(4) . . . . ? C5 N1 C1 C2 13.7(6) . . . . ? N1 C1 C2 C9 -178.1(4) . . . . ? N1 C1 C2 C3 10.2(6) . . . . ? C1 C2 C3 C4 -13.1(7) . . . . ? C9 C2 C3 C4 174.8(5) . . . . ? C2 C3 C4 C5 -7.7(7) . . . . ? C1 N1 C5 C4 -31.5(6) . . . . ? C8 N1 C5 C4 149.9(4) . . . . ? C1 N1 C5 C6 -155.4(4) . . . . ? C8 N1 C5 C6 26.0(5) . . . . ? C1 N1 C5 C13 88.8(5) . . . . ? C8 N1 C5 C13 -89.8(4) . . . . ? C3 C4 C5 N1 28.2(6) . . . . ? C3 C4 C5 C6 142.6(5) . . . . ? C3 C4 C5 C13 -91.4(6) . . . . ? N1 C5 C6 C7 -34.1(5) . . . . ? C4 C5 C6 C7 -152.6(4) . . . . ? C13 C5 C6 C7 81.1(5) . . . . ? C5 C6 C7 C8 31.2(5) . . . . ? C1 N1 C8 C7 174.4(4) . . . . ? C5 N1 C8 C7 -7.1(5) . . . . ? C6 C7 C8 N1 -15.4(5) . . . . ? C10 O1 C9 O2 -2.6(7) . . . . ? C10 O1 C9 C2 176.9(4) . . . . ? C1 C2 C9 O2 -175.8(5) . . . . ? C3 C2 C9 O2 -4.3(8) . . . . ? C1 C2 C9 O1 4.7(6) . . . . ? C3 C2 C9 O1 176.2(4) . . . . ? C9 O1 C10 C12 -82.3(6) . . . . ? C9 O1 C10 C11 155.5(5) . . . . ? C14 O3 C13 O4 -1.9(8) . . . . ? C14 O3 C13 C5 175.8(4) . . . . ? N1 C5 C13 O4 5.9(7) . . . . ? C4 C5 C13 O4 125.6(6) . . . . ? C6 C5 C13 O4 -104.5(6) . . . . ? N1 C5 C13 O3 -171.8(4) . . . . ? C4 C5 C13 O3 -52.0(6) . . . . ? C6 C5 C13 O3 77.9(5) . . . . ? C13 O3 C14 C15 87.6(6) . . . . ? C13 O3 C14 C16 -149.9(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.180 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.052 data_compound_29 _database_code_CSD 159040 _audit_creation_date '19100-10-24' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #--------------------------------------------------------------------------- _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H25 N O4' _chemical_formula_weight 295.37 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 triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.310 _cell_length_b 10.038 _cell_length_c 12.314 _cell_angle_alpha 111.20 _cell_angle_beta 93.03 _cell_angle_gamma 95.48 _cell_volume 834.8 _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 'one image' _cell_measurement_theta_min 5 _cell_measurement_theta_max 20 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku RAXIS' _diffrn_measurement_method '90 x 4 degree phi scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 14636 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.31 _reflns_number_total 2152 _reflns_number_gt 1843 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_publication_material 'teXsan (MSC, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.1042P] 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_number_reflns 2152 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.33962(17) 0.23738(13) 0.80089(10) 0.0597(4) Uani 1 d . . . O2 O 0.47184(19) 0.44647(14) 0.79399(11) 0.0711(4) Uani 1 d . . . O3 O 0.11872(16) 0.29946(13) 0.31433(11) 0.0590(4) Uani 1 d . . . O4 O -0.04627(17) 0.16309(15) 0.39216(13) 0.0700(4) Uani 1 d . . . N1 N 0.25632(19) 0.05066(13) 0.44417(11) 0.0451(4) Uani 1 d . . . C1 C 0.2946(2) 0.11470(17) 0.56103(14) 0.0434(4) Uani 1 d . . . H1 H 0.2714 0.0598 0.6067 0.052 Uiso 1 calc R . . C2 C 0.3657(2) 0.25566(17) 0.61584(14) 0.0448(4) Uani 1 d . . . C3 C 0.4201(3) 0.34571(18) 0.54458(15) 0.0533(5) Uani 1 d . . . H3A H 0.5356 0.4060 0.5797 0.064 Uiso 1 calc R . . H3B H 0.3265 0.4082 0.5452 0.064 Uiso 1 calc R . . C4 C 0.4419(2) 0.25060(18) 0.41833(15) 0.0518(5) Uani 1 d . . . H4A H 0.5544 0.2060 0.4158 0.062 Uiso 1 calc R . . H4B H 0.4519 0.3094 0.3709 0.062 Uiso 1 calc R . . C5 C 0.2769(2) 0.13374(17) 0.36826(14) 0.0452(4) Uani 1 d . . . C6 C 0.2977(3) 0.0158(2) 0.24950(16) 0.0600(5) Uani 1 d . . . H6A H 0.2535 0.0424 0.1854 0.072 Uiso 1 calc R . . H6B H 0.4255 -0.0015 0.2419 0.072 Uiso 1 calc R . . C7 C 0.1792(3) -0.1160(2) 0.25156(16) 0.0652(5) Uani 1 d . . . H7A H 0.2235 -0.2036 0.2017 0.078 Uiso 1 calc R . . H7B H 0.0516 -0.1167 0.2250 0.078 Uiso 1 calc R . . C8 C 0.1967(2) -0.10314(17) 0.37898(15) 0.0494(4) Uani 1 d . . . H8A H 0.0793 -0.1328 0.4017 0.059 Uiso 1 calc R . . H8B H 0.2876 -0.1614 0.3920 0.059 Uiso 1 calc R . . C9 C 0.3987(2) 0.32317(19) 0.74247(16) 0.0519(5) Uani 1 d . . . C10 C 0.3574(3) 0.3031(2) 0.92907(15) 0.0633(5) Uani 1 d . . . H10 H 0.4777 0.3619 0.9562 0.076 Uiso 1 calc R . . C11 C 0.3481(4) 0.1811(3) 0.9726(2) 0.0994(8) Uani 1 d . . . H11A H 0.2332 0.1203 0.9424 0.149 Uiso 1 calc R . . H11B H 0.3564 0.2190 1.0566 0.149 Uiso 1 calc R . . H11C H 0.4486 0.1262 0.9467 0.149 Uiso 1 calc R . . C12 C 0.2064(3) 0.3973(2) 0.96928(18) 0.0804(7) Uani 1 d . . . H12A H 0.2119 0.4686 0.9341 0.121 Uiso 1 calc R . . H12B H 0.2226 0.4441 1.0529 0.121 Uiso 1 calc R . . H12C H 0.0885 0.3391 0.9464 0.121 Uiso 1 calc R . . C13 C 0.0971(2) 0.19853(17) 0.36112(14) 0.0466(4) Uani 1 d . . . C14 C -0.0420(2) 0.3714(2) 0.30139(17) 0.0598(5) Uani 1 d . . . H14 H -0.1184 0.3791 0.3659 0.072 Uiso 1 calc R . . C15 C 0.0355(3) 0.5196(2) 0.31102(19) 0.0714(6) Uani 1 d . . . H15A H 0.1006 0.5698 0.3870 0.107 Uiso 1 calc R . . H15B H -0.0634 0.5713 0.3002 0.107 Uiso 1 calc R . . H15C H 0.1188 0.5124 0.2520 0.107 Uiso 1 calc R . . C16 C -0.1533(3) 0.2842(2) 0.1875(2) 0.0918(8) Uani 1 d . . . H16A H -0.0773 0.2729 0.1242 0.138 Uiso 1 calc R . . H16B H -0.2563 0.3327 0.1775 0.138 Uiso 1 calc R . . H16C H -0.1977 0.1912 0.1878 0.138 Uiso 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 0.0731(9) 0.0574(8) 0.0442(7) 0.0152(6) 0.0039(6) 0.0022(7) O2 0.0771(9) 0.0590(8) 0.0638(9) 0.0136(7) -0.0080(7) -0.0113(7) O3 0.0519(7) 0.0671(8) 0.0799(9) 0.0492(7) 0.0165(6) 0.0183(6) O4 0.0510(8) 0.0845(10) 0.0988(11) 0.0602(9) 0.0179(7) 0.0117(7) N1 0.0542(8) 0.0376(7) 0.0462(9) 0.0189(6) 0.0035(6) 0.0048(6) C1 0.0385(9) 0.0496(10) 0.0481(11) 0.0242(8) 0.0044(7) 0.0097(8) C2 0.0415(9) 0.0440(9) 0.0488(10) 0.0173(8) 0.0014(7) 0.0049(8) C3 0.0505(10) 0.0468(10) 0.0636(12) 0.0240(9) -0.0001(8) -0.0004(8) C4 0.0463(10) 0.0555(10) 0.0633(12) 0.0322(9) 0.0102(8) 0.0078(8) C5 0.0488(10) 0.0456(9) 0.0477(10) 0.0236(8) 0.0081(7) 0.0088(8) C6 0.0717(13) 0.0606(11) 0.0507(11) 0.0206(9) 0.0131(9) 0.0182(10) C7 0.0783(13) 0.0531(11) 0.0568(12) 0.0120(9) 0.0012(10) 0.0089(10) C8 0.0478(10) 0.0410(9) 0.0585(11) 0.0175(8) 0.0021(8) 0.0072(8) C9 0.0458(10) 0.0513(11) 0.0572(12) 0.0191(9) -0.0002(8) 0.0050(9) C10 0.0677(12) 0.0726(13) 0.0419(11) 0.0137(9) -0.0009(9) 0.0052(11) C11 0.144(2) 0.1007(19) 0.0622(15) 0.0377(14) 0.0144(14) 0.0249(17) C12 0.0759(14) 0.0918(16) 0.0576(13) 0.0086(11) 0.0060(10) 0.0106(13) C13 0.0497(10) 0.0476(10) 0.0474(10) 0.0234(8) 0.0050(8) 0.0051(8) C14 0.0538(11) 0.0671(12) 0.0736(13) 0.0404(10) 0.0097(9) 0.0201(10) C15 0.0722(14) 0.0639(13) 0.0882(16) 0.0384(11) 0.0051(11) 0.0169(11) C16 0.0900(17) 0.0786(15) 0.109(2) 0.0431(14) -0.0224(14) 0.0044(13) _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 C9 1.362(2) . ? O1 C10 1.467(2) . ? O2 C9 1.221(2) . ? O3 C13 1.3359(19) . ? O3 C14 1.467(2) . ? O4 C13 1.200(2) . ? N1 C1 1.348(2) . ? N1 C8 1.468(2) . ? N1 C5 1.465(2) . ? C1 C2 1.364(2) . ? C1 H1 0.9300 . ? C2 C9 1.454(2) . ? C2 C3 1.512(2) . ? C3 C4 1.528(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.530(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C13 1.533(2) . ? C5 C6 1.539(2) . ? C6 C7 1.519(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.525(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C11 1.501(3) . ? C10 C12 1.509(3) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C14 C16 1.501(3) . ? C14 C15 1.500(3) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 C9 O1 C10 116.76(14) . . ? C13 O3 C14 117.83(13) . . ? C1 N1 C8 126.12(13) . . ? C1 N1 C5 120.86(13) . . ? C8 N1 C5 113.00(13) . . ? N1 C1 C2 123.48(15) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C9 122.17(15) . . ? C1 C2 C3 120.07(15) . . ? C9 C2 C3 117.71(14) . . ? C2 C3 C4 111.12(14) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 110.73(13) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? N1 C5 C4 109.16(13) . . ? N1 C5 C13 108.27(13) . . ? C4 C5 C13 111.62(14) . . ? N1 C5 C6 101.96(13) . . ? C4 C5 C6 115.54(14) . . ? C13 C5 C6 109.66(14) . . ? C7 C6 C5 103.92(14) . . ? C7 C6 H6A 111.0 . . ? C5 C6 H6A 111.0 . . ? C7 C6 H6B 111.0 . . ? C5 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? C6 C7 C8 105.17(14) . . ? C6 C7 H7A 110.7 . . ? C8 C7 H7A 110.7 . . ? C6 C7 H7B 110.7 . . ? C8 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? N1 C8 C7 103.83(14) . . ? N1 C8 H8A 111.0 . . ? C7 C8 H8A 111.0 . . ? N1 C8 H8B 111.0 . . ? C7 C8 H8B 111.0 . . ? H8A C8 H8B 109.0 . . ? O2 C9 O1 121.78(16) . . ? O2 C9 C2 123.84(17) . . ? O1 C9 C2 114.38(14) . . ? O1 C10 C11 106.40(16) . . ? O1 C10 C12 109.83(15) . . ? C11 C10 C12 112.6(2) . . ? O1 C10 H10 109.3 . . ? C11 C10 H10 109.3 . . ? C12 C10 H10 109.3 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O4 C13 O3 123.69(16) . . ? O4 C13 C5 124.92(15) . . ? O3 C13 C5 111.39(14) . . ? O3 C14 C16 109.28(17) . . ? O3 C14 C15 105.43(14) . . ? C16 C14 C15 114.33(17) . . ? O3 C14 H14 109.2 . . ? C16 C14 H14 109.2 . . ? C15 C14 H14 109.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C8 N1 C1 C2 173.76(15) . . . . ? C5 N1 C1 C2 -4.6(2) . . . . ? N1 C1 C2 C9 177.51(14) . . . . ? N1 C1 C2 C3 -5.0(2) . . . . ? C1 C2 C3 C4 -17.8(2) . . . . ? C9 C2 C3 C4 159.85(14) . . . . ? C2 C3 C4 C5 47.66(19) . . . . ? C1 N1 C5 C4 35.20(19) . . . . ? C8 N1 C5 C4 -143.34(14) . . . . ? C1 N1 C5 C13 -86.51(17) . . . . ? C8 N1 C5 C13 94.95(15) . . . . ? C1 N1 C5 C6 157.89(14) . . . . ? C8 N1 C5 C6 -20.65(18) . . . . ? C3 C4 C5 N1 -55.92(17) . . . . ? C3 C4 C5 C13 63.74(18) . . . . ? C3 C4 C5 C6 -170.07(14) . . . . ? N1 C5 C6 C7 32.75(17) . . . . ? C4 C5 C6 C7 150.98(15) . . . . ? C13 C5 C6 C7 -81.83(17) . . . . ? C5 C6 C7 C8 -33.87(18) . . . . ? C1 N1 C8 C7 -178.41(15) . . . . ? C5 N1 C8 C7 0.04(18) . . . . ? C6 C7 C8 N1 21.16(18) . . . . ? C10 O1 C9 O2 3.8(2) . . . . ? C10 O1 C9 C2 -175.79(14) . . . . ? C1 C2 C9 O2 175.59(17) . . . . ? C3 C2 C9 O2 -2.0(3) . . . . ? C1 C2 C9 O1 -4.9(2) . . . . ? C3 C2 C9 O1 177.57(14) . . . . ? C9 O1 C10 C11 -160.76(18) . . . . ? C9 O1 C10 C12 77.1(2) . . . . ? C14 O3 C13 O4 0.6(2) . . . . ? C14 O3 C13 C5 179.85(14) . . . . ? N1 C5 C13 O4 -13.9(2) . . . . ? C4 C5 C13 O4 -134.08(18) . . . . ? C6 C5 C13 O4 96.6(2) . . . . ? N1 C5 C13 O3 166.82(13) . . . . ? C4 C5 C13 O3 46.64(18) . . . . ? C6 C5 C13 O3 -82.71(17) . . . . ? C13 O3 C14 C16 -86.3(2) . . . . ? C13 O3 C14 C15 150.33(16) . . . . ? _diffrn_measured_fraction_theta_max 0.633 _diffrn_reflns_theta_full 26.31 _diffrn_measured_fraction_theta_full 0.633 _refine_diff_density_max 0.120 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.028