# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_exp_848 _audit_creation_date 2013-03-28 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H20 O5' _chemical_formula_sum 'C9 H0 N8 O4' _chemical_formula_weight 284.17 _chemical_absolute_configuration unk _chemical_melting_point ? 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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 8.7505(5) _cell_length_b 10.8915(6) _cell_length_c 15.6217(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1488.85(14) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1501 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.7210 _cell_measurement_theta_min 3.9540 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89372 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_unetI/netI 0.0512 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 3946 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.99 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9955 _diffrn_measured_fraction_theta_max 0.7913 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -81.00 -40.50 1.5000 6.0000 omega____ theta____ kappa____ phi______ frames - -19.3700 -57.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 2 omega -45.00 69.00 1.5000 6.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 -19.0000 0.0000 76 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0533609000 _diffrn_orient_matrix_UB_12 0.0352569000 _diffrn_orient_matrix_UB_13 -0.0237558000 _diffrn_orient_matrix_UB_21 -0.0251410000 _diffrn_orient_matrix_UB_22 -0.0539056000 _diffrn_orient_matrix_UB_23 -0.0211861000 _diffrn_orient_matrix_UB_31 -0.0555773000 _diffrn_orient_matrix_UB_32 -0.0094731000 _diffrn_orient_matrix_UB_33 0.0324083000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2239 _reflns_number_total 2759 _reflns_odcompleteness_completeness 99.55 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.267 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(16) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 2759 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0501 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.2195P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1048 _refine_ls_wR_factor_ref 0.1157 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H3 of C3, {H4A,H4B} of C4, H6 of C6, {H10A,H10B} of C10, H11 of C11 At 1.5 times of: H4 of O4, {H16A,H16B,H16C} of C16, {H15A,H15B,H15C} of C15, {H14A,H14B, H14C} of C14, {H13A,H13B,H13C} of C13 2.a Ternary CH refined with riding coordinates: C3(H3), C11(H11) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C10(H10A,H10B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B, H16C) 2.e Idealised tetrahedral OH refined as rotating group: O4(H4) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 -0.1041(2) -0.6632(2) -0.73018(13) 0.0567(6) Uani 1 1 d . . . O2 O -0.0033(2) -0.51068(19) -0.65974(12) 0.0439(5) Uani 1 1 d . . . O3 O -0.41411(19) -0.67639(17) -0.72072(10) 0.0347(4) Uani 1 1 d . . . O4 O -0.8130(2) -0.7720(2) -0.72587(15) 0.0548(6) Uani 1 1 d . . . H4 H -0.8909 -0.7303 -0.7268 0.082 Uiso 1 1 calc R . . O5 O -0.6180(2) -0.5855(2) -0.44815(11) 0.0546(6) Uani 1 1 d . . . C1 C -0.2577(3) -0.5760(2) -0.61954(15) 0.0299(6) Uani 1 1 d . . . C2 C -0.1229(3) -0.5870(3) -0.67502(17) 0.0374(6) Uani 1 1 d . . . C3 C -0.0235(3) -0.4082(3) -0.60076(17) 0.0409(7) Uani 1 1 d . . . H3 H -0.0929 -0.3478 -0.6263 0.049 Uiso 1 1 calc R . . C4 C -0.0927(4) -0.4569(3) -0.51986(17) 0.0450(7) Uani 1 1 d . . . H4A H -0.1096 -0.3900 -0.4800 0.054 Uiso 1 1 calc R . . H4B H -0.0233 -0.5151 -0.4934 0.054 Uiso 1 1 calc R . . C5 C -0.2421(3) -0.5189(3) -0.53992(16) 0.0343(6) Uani 1 1 d . . . C6 C -0.3602(3) -0.5199(3) -0.48088(17) 0.0391(7) Uani 1 1 d . . . H6 H -0.3482 -0.4822 -0.4279 0.047 Uiso 1 1 calc R . . C7 C -0.4963(3) -0.5776(3) -0.50166(15) 0.0364(6) Uani 1 1 d . . . C8 C -0.5195(3) -0.6315(2) -0.58230(15) 0.0315(6) Uani 1 1 d . . . C9 C -0.3995(3) -0.6308(2) -0.64035(15) 0.0285(5) Uani 1 1 d . . . C10 C -0.6718(3) -0.6868(3) -0.60556(17) 0.0391(7) Uani 1 1 d . . . H10A H -0.7535 -0.6356 -0.5833 0.047 Uiso 1 1 calc R . . H10B H -0.6811 -0.7675 -0.5799 0.047 Uiso 1 1 calc R . . C11 C -0.6866(3) -0.6971(3) -0.70206(17) 0.0356(6) Uani 1 1 d . . . H11 H -0.7005 -0.6149 -0.7263 0.043 Uiso 1 1 calc R . . C12 C -0.5449(3) -0.7547(2) -0.74087(16) 0.0323(6) Uani 1 1 d . . . C13 C 0.1339(4) -0.3510(3) -0.5899(2) 0.0582(9) Uani 1 1 d . . . H13A H 0.2021 -0.4101 -0.5651 0.087 Uiso 1 1 calc R . . H13B H 0.1266 -0.2807 -0.5531 0.087 Uiso 1 1 calc R . . H13C H 0.1723 -0.3261 -0.6448 0.087 Uiso 1 1 calc R . . C14 C -0.6011(4) -0.5348(4) -0.36370(18) 0.0714(11) Uani 1 1 d . . . H14A H -0.5901 -0.4472 -0.3676 0.107 Uiso 1 1 calc R . . H14B H -0.5121 -0.5691 -0.3369 0.107 Uiso 1 1 calc R . . H14C H -0.6899 -0.5540 -0.3302 0.107 Uiso 1 1 calc R . . C15 C -0.5132(4) -0.8817(2) -0.7077(2) 0.0499(8) Uani 1 1 d . . . H15A H -0.4317 -0.9180 -0.7401 0.075 Uiso 1 1 calc R . . H15B H -0.6035 -0.9311 -0.7132 0.075 Uiso 1 1 calc R . . H15C H -0.4841 -0.8771 -0.6485 0.075 Uiso 1 1 calc R . . C16 C -0.5520(3) -0.7521(3) -0.83806(17) 0.0479(8) Uani 1 1 d . . . H16A H -0.5705 -0.6696 -0.8571 0.072 Uiso 1 1 calc R . . H16B H -0.6333 -0.8044 -0.8574 0.072 Uiso 1 1 calc R . . H16C H -0.4568 -0.7807 -0.8611 0.072 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 0.0319(11) 0.0768(16) 0.0613(13) -0.0286(13) 0.0063(11) -0.0049(11) O2 0.0278(10) 0.0569(13) 0.0469(10) -0.0035(10) -0.0012(9) -0.0101(10) O3 0.0270(9) 0.0442(11) 0.0328(9) -0.0064(8) 0.0003(8) -0.0061(8) O4 0.0299(11) 0.0631(14) 0.0716(13) -0.0212(12) -0.0036(12) -0.0067(11) O5 0.0437(12) 0.0813(16) 0.0388(10) -0.0134(11) 0.0136(10) -0.0106(12) C1 0.0272(13) 0.0311(13) 0.0316(12) 0.0027(11) -0.0038(11) 0.0016(11) C2 0.0258(14) 0.0450(16) 0.0413(14) 0.0010(14) -0.0031(13) -0.0016(13) C3 0.0342(15) 0.0443(17) 0.0443(14) 0.0034(14) -0.0101(13) -0.0064(14) C4 0.0434(17) 0.0532(18) 0.0383(14) -0.0024(14) -0.0080(14) -0.0113(15) C5 0.0312(14) 0.0351(15) 0.0365(13) 0.0033(12) -0.0040(12) -0.0019(13) C6 0.0411(16) 0.0434(16) 0.0327(13) -0.0048(13) -0.0008(13) -0.0019(14) C7 0.0335(14) 0.0419(15) 0.0337(13) 0.0011(13) 0.0043(13) 0.0030(13) C8 0.0265(13) 0.0340(14) 0.0342(13) -0.0007(11) 0.0010(12) 0.0019(12) C9 0.0288(13) 0.0263(12) 0.0304(12) -0.0007(10) -0.0024(12) 0.0002(11) C10 0.0288(14) 0.0445(17) 0.0442(15) -0.0046(14) 0.0052(13) -0.0030(13) C11 0.0234(13) 0.0372(15) 0.0463(15) -0.0058(13) -0.0022(13) -0.0024(12) C12 0.0242(14) 0.0342(14) 0.0386(13) -0.0038(13) -0.0007(12) -0.0039(11) C13 0.0480(19) 0.062(2) 0.065(2) 0.0062(18) -0.0105(17) -0.0218(17) C14 0.061(2) 0.109(3) 0.0451(17) -0.024(2) 0.0165(18) -0.005(2) C15 0.0483(18) 0.0326(15) 0.069(2) -0.0029(15) 0.0023(17) 0.0019(14) C16 0.0377(16) 0.065(2) 0.0409(15) -0.0081(16) -0.0007(14) -0.0057(16) _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 C2 1.208(3) . ? O2 C2 1.358(3) . ? O2 C3 1.458(3) . ? O3 C9 1.356(3) . ? O3 C12 1.461(3) . ? O4 C11 1.424(3) . ? O5 C7 1.356(3) . ? O5 C14 1.438(3) . ? C1 C2 1.469(4) . ? C1 C5 1.397(3) . ? C1 C9 1.414(3) . ? C3 C4 1.498(4) . ? C3 C13 1.521(4) . ? C4 C5 1.505(4) . ? C5 C6 1.385(4) . ? C6 C7 1.386(4) . ? C7 C8 1.405(3) . ? C8 C9 1.387(3) . ? C8 C10 1.507(4) . ? C10 C11 1.517(4) . ? C11 C12 1.516(3) . ? C12 C15 1.503(4) . ? C12 C16 1.520(4) . ? 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 O2 C3 119.1(2) . . ? C9 O3 C12 119.15(19) . . ? C7 O5 C14 117.4(2) . . ? C5 C1 C2 118.9(2) . . ? C5 C1 C9 118.6(2) . . ? C9 C1 C2 122.3(2) . . ? O1 C2 O2 116.2(2) . . ? O1 C2 C1 125.9(3) . . ? O2 C2 C1 117.8(2) . . ? O2 C3 C4 108.1(2) . . ? O2 C3 C13 105.9(2) . . ? C4 C3 C13 114.6(2) . . ? C3 C4 C5 109.5(2) . . ? C1 C5 C4 118.0(2) . . ? C6 C5 C1 121.1(2) . . ? C6 C5 C4 120.8(2) . . ? C5 C6 C7 119.2(2) . . ? O5 C7 C6 124.0(2) . . ? O5 C7 C8 114.4(2) . . ? C6 C7 C8 121.6(2) . . ? C7 C8 C10 120.7(2) . . ? C9 C8 C7 118.4(2) . . ? C9 C8 C10 120.9(2) . . ? O3 C9 C1 116.8(2) . . ? O3 C9 C8 122.1(2) . . ? C8 C9 C1 121.0(2) . . ? C8 C10 C11 110.1(2) . . ? O4 C11 C10 111.6(2) . . ? O4 C11 C12 107.1(2) . . ? C12 C11 C10 111.0(2) . . ? O3 C12 C11 108.2(2) . . ? O3 C12 C15 108.6(2) . . ? O3 C12 C16 103.7(2) . . ? C11 C12 C16 111.0(2) . . ? C15 C12 C11 113.2(2) . . ? C15 C12 C16 111.7(3) . . ? _database_code_depnum_ccdc_archive 'CCDC 938907'