# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_xw10 _database_code_depnum_ccdc_archive 'CCDC 835399' #TrackingRef 'xw10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 N2 O6, 0.5(H2 O)' _chemical_formula_sum 'C10 H15 N2 O6.50' _chemical_formula_weight 267.24 _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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 13.9973(5) _cell_length_b 17.2440(6) _cell_length_c 4.8028(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1159.25(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9892 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 30.46 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9573 _exptl_absorpt_correction_T_max 0.9672 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method '\w scans at 9 \f settings' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30650 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 30.52 _reflns_number_total 3535 _reflns_number_gt 3342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v5.630' _computing_cell_refinement 'Bruker SAINT-Plus v7.66A' _computing_data_reduction 'Bruker SAINT-Plus v7.66A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker XP v5.1' _computing_publication_material 'Bruker XCIF 2008' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type 'Full matrix' _refine_ls_weighting_scheme Sigma _refine_ls_weighting_details w=1/s^2^(Fo^2^) _atom_sites_solution_primary 'Direct methods' _atom_sites_solution_secondary 'Difference Fourier map' _atom_sites_solution_hydrogens 'Difference Fourier map' _refine_ls_hydrogen_treatment Unrestrained _chemical_absolute_configuration ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(6) _refine_ls_number_reflns 3535 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0558 _refine_ls_wR_factor_gt 0.0554 _refine_ls_goodness_of_fit_ref 2.877 _refine_ls_restrained_S_all 2.877 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _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 0.79142(5) 0.34093(4) 0.71108(16) 0.01332(16) Uani 1 1 d . . . O2 O 0.63185(6) 0.41169(5) 0.39154(18) 0.01589(17) Uani 1 1 d . . . O3 O 0.87561(6) 0.50776(5) 0.32991(17) 0.01588(17) Uani 1 1 d . . . O4 O 0.99160(6) 0.40749(5) 0.63228(18) 0.01758(18) Uani 1 1 d . . . O5 O 0.99355(6) 0.19022(5) 0.45507(18) 0.01796(18) Uani 1 1 d . . . O6 O 0.78819(6) 0.07838(5) -0.15967(18) 0.02026(19) Uani 1 1 d . . . N1 N 0.84704(6) 0.24595(5) 0.3956(2) 0.01195(19) Uani 1 1 d . . . N2 N 0.88821(7) 0.13549(5) 0.1479(2) 0.0138(2) Uani 1 1 d . . . C1 C 0.78396(8) 0.42292(6) 0.6431(2) 0.0114(2) Uani 1 1 d . . . C2 C 0.68002(8) 0.44567(7) 0.6257(3) 0.0152(2) Uani 1 1 d . . . C3 C 0.84323(7) 0.43115(6) 0.3794(2) 0.0107(2) Uani 1 1 d . . . C4 C 0.92648(8) 0.37609(6) 0.4383(2) 0.0125(2) Uani 1 1 d . . . C5 C 0.87516(8) 0.30958(6) 0.5887(2) 0.0117(2) Uani 1 1 d . . . C6 C 0.91484(7) 0.19005(6) 0.3415(2) 0.0126(2) Uani 1 1 d . . . C7 C 0.80123(8) 0.13136(6) 0.0103(2) 0.0136(2) Uani 1 1 d . . . C8 C 0.73327(7) 0.19118(6) 0.0782(2) 0.0122(2) Uani 1 1 d . . . C9 C 0.63753(8) 0.19190(7) -0.0634(3) 0.0166(2) Uani 1 1 d . . . C10 C 0.75927(8) 0.24572(7) 0.2641(2) 0.0122(2) Uani 1 1 d . . . H1N H 0.9302(10) 0.1000(8) 0.109(3) 0.026(4) Uiso 1 1 d . . . H1 H 0.8148(8) 0.4527(7) 0.793(3) 0.010(3) Uiso 1 1 d . . . H2 H 0.5918(12) 0.3816(10) 0.454(4) 0.047(5) Uiso 1 1 d . . . H3 H 0.8274(11) 0.5338(9) 0.275(3) 0.037(5) Uiso 1 1 d . . . H4 H 1.0307(11) 0.4374(8) 0.537(4) 0.035(5) Uiso 1 1 d . . . H5 H 0.9155(8) 0.2857(7) 0.734(3) 0.011(3) Uiso 1 1 d . . . H10 H 0.7204(9) 0.2876(7) 0.322(3) 0.010(3) Uiso 1 1 d . . . H2A H 0.6485(9) 0.4336(7) 0.799(3) 0.014(3) Uiso 1 1 d . . . H3A H 0.8062(8) 0.4108(6) 0.223(2) 0.003(3) Uiso 1 1 d . . . H4A H 0.9576(8) 0.3567(6) 0.270(3) 0.008(3) Uiso 1 1 d . . . H9A H 0.5993(9) 0.1468(8) -0.009(3) 0.027(4) Uiso 1 1 d . . . H2B H 0.6769(8) 0.5044(7) 0.602(2) 0.009(3) Uiso 1 1 d . . . H9B H 0.6452(9) 0.1876(8) -0.260(3) 0.027(4) Uiso 1 1 d . . . H9C H 0.6007(10) 0.2408(9) -0.015(3) 0.030(4) Uiso 1 1 d . . . O11 O 0.5000 0.5000 0.0594(3) 0.0161(2) Uani 1 2 d S . . H11 H 0.5453(10) 0.4811(9) 0.172(3) 0.045(5) Uiso 1 1 d . . . _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 0.0155(4) 0.0095(4) 0.0150(4) 0.0018(3) 0.0038(3) 0.0003(3) O2 0.0127(4) 0.0158(4) 0.0193(4) 0.0016(4) 0.0001(3) -0.0030(3) O3 0.0140(4) 0.0116(4) 0.0221(4) 0.0060(3) -0.0008(3) -0.0017(3) O4 0.0142(4) 0.0152(4) 0.0233(4) 0.0026(4) -0.0073(3) -0.0043(3) O5 0.0130(4) 0.0154(4) 0.0255(4) -0.0019(4) -0.0044(3) 0.0025(3) O6 0.0186(4) 0.0171(4) 0.0251(5) -0.0083(4) -0.0029(4) 0.0004(3) N1 0.0116(4) 0.0087(4) 0.0155(5) -0.0010(4) -0.0015(4) 0.0004(3) N2 0.0115(5) 0.0107(4) 0.0193(5) -0.0025(4) 0.0001(4) 0.0022(4) C1 0.0149(5) 0.0080(5) 0.0112(5) 0.0003(4) 0.0014(4) -0.0005(4) C2 0.0150(5) 0.0148(6) 0.0156(6) -0.0012(5) 0.0028(5) 0.0012(4) C3 0.0104(5) 0.0094(5) 0.0123(5) 0.0005(4) 0.0006(4) -0.0017(4) C4 0.0106(5) 0.0121(5) 0.0148(6) 0.0002(4) -0.0001(4) -0.0012(4) C5 0.0123(5) 0.0102(5) 0.0125(5) -0.0006(4) -0.0021(4) 0.0007(4) C6 0.0121(5) 0.0095(5) 0.0163(6) 0.0027(5) 0.0004(4) -0.0012(4) C7 0.0136(5) 0.0127(5) 0.0147(5) 0.0022(4) 0.0005(4) -0.0025(4) C8 0.0116(5) 0.0107(5) 0.0142(5) 0.0012(4) -0.0005(4) -0.0013(4) C9 0.0139(6) 0.0176(6) 0.0183(6) -0.0023(5) -0.0034(5) 0.0000(5) C10 0.0097(5) 0.0121(5) 0.0149(5) 0.0022(4) 0.0007(4) 0.0014(4) O11 0.0124(6) 0.0173(6) 0.0185(6) 0.000 0.000 0.0022(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. ; _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 C5 1.4183(13) . ? O1 C1 1.4550(13) . ? O2 C2 1.4361(15) . ? O2 H2 0.820(17) . ? O3 C3 1.4167(13) . ? O3 H3 0.853(15) . ? O4 C4 1.4115(13) . ? O4 H4 0.879(16) . ? O5 C6 1.2293(13) . ? O6 C7 1.2387(14) . ? N1 C6 1.3775(14) . ? N1 C10 1.3812(14) . ? N1 C5 1.4897(14) . ? N2 C6 1.3743(14) . ? N2 C7 1.3871(14) . ? N2 H1N 0.868(14) . ? C1 C2 1.5093(16) . ? C1 C3 1.5204(15) . ? C1 H1 0.985(12) . ? C2 H2A 0.964(13) . ? C2 H2B 1.021(12) . ? C3 C4 1.5294(15) . ? C3 H3A 0.976(11) . ? C4 C5 1.5343(15) . ? C4 H4A 0.975(12) . ? C5 H5 0.988(12) . ? C7 C8 1.4406(15) . ? C8 C10 1.3469(16) . ? C8 C9 1.5029(15) . ? C9 H9A 0.979(14) . ? C9 H9B 0.953(15) . ? C9 H9C 1.016(15) . ? C10 H10 0.946(12) . ? O11 H11 0.895(15) . ? _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 C5 O1 C1 109.68(8) . . ? C2 O2 H2 107.1(13) . . ? C3 O3 H3 106.8(10) . . ? C4 O4 H4 106.5(11) . . ? C6 N1 C10 121.64(9) . . ? C6 N1 C5 116.79(8) . . ? C10 N1 C5 121.45(9) . . ? C6 N2 C7 126.55(10) . . ? C6 N2 H1N 116.3(10) . . ? C7 N2 H1N 117.1(10) . . ? O1 C1 C2 109.52(9) . . ? O1 C1 C3 103.80(8) . . ? C2 C1 C3 117.11(10) . . ? O1 C1 H1 108.1(7) . . ? C2 C1 H1 109.1(7) . . ? C3 C1 H1 108.8(7) . . ? O2 C2 C1 112.95(9) . . ? O2 C2 H2A 111.8(7) . . ? C1 C2 H2A 109.7(8) . . ? O2 C2 H2B 107.2(6) . . ? C1 C2 H2B 107.8(6) . . ? H2A C2 H2B 107.0(10) . . ? O3 C3 C1 113.67(9) . . ? O3 C3 C4 111.47(9) . . ? C1 C3 C4 101.77(9) . . ? O3 C3 H3A 112.1(6) . . ? C1 C3 H3A 108.4(6) . . ? C4 C3 H3A 108.9(6) . . ? O4 C4 C3 112.07(9) . . ? O4 C4 C5 106.15(9) . . ? C3 C4 C5 101.20(8) . . ? O4 C4 H4A 112.9(7) . . ? C3 C4 H4A 113.6(7) . . ? C5 C4 H4A 110.0(7) . . ? O1 C5 N1 108.68(8) . . ? O1 C5 C4 107.29(9) . . ? N1 C5 C4 112.40(9) . . ? O1 C5 H5 109.8(7) . . ? N1 C5 H5 106.5(7) . . ? C4 C5 H5 112.2(7) . . ? O5 C6 N2 123.02(10) . . ? O5 C6 N1 122.15(10) . . ? N2 C6 N1 114.82(9) . . ? O6 C7 N2 118.76(10) . . ? O6 C7 C8 125.45(10) . . ? N2 C7 C8 115.79(10) . . ? C10 C8 C7 118.14(10) . . ? C10 C8 C9 122.36(10) . . ? C7 C8 C9 119.49(10) . . ? C8 C9 H9A 111.1(8) . . ? C8 C9 H9B 110.3(8) . . ? H9A C9 H9B 105.2(12) . . ? C8 C9 H9C 110.8(8) . . ? H9A C9 H9C 108.7(11) . . ? H9B C9 H9C 110.5(12) . . ? C8 C10 N1 123.05(10) . . ? C8 C10 H10 124.9(7) . . ? N1 C10 H10 112.0(7) . . ? _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H1N O11 0.868(14) 2.142(14) 2.9830(10) 163.2(13) 3 O2 H2 O5 0.820(17) 1.902(17) 2.7163(11) 171.9(18) 3_456 O3 H3 O6 0.853(15) 1.875(16) 2.7219(12) 172.1(15) 4_655 O4 H4 O3 0.879(16) 1.899(16) 2.7748(11) 173.7(14) 2_765 O11 H11 O2 0.895(15) 2.003(15) 2.8756(10) 164.7(15) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.269 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.052