# 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_C13H19Cl3O6compound2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Sugar _chemical_melting_point '136-138 degree centigrade' _chemical_formula_moiety 'C13 H19 Cl3 O6' _chemical_formula_sum 'C13 H19 Cl3 O6' _chemical_formula_weight 377.63 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.8916(4) _cell_length_b 9.9811(6) _cell_length_c 14.2720(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.639(1) _cell_angle_gamma 90.00 _cell_volume 839.21(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3785 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.97 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.570 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8042 _exptl_absorpt_correction_T_max 0.9194 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4225 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2381 _reflns_number_gt 2355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, PyMOL and PLATON' _computing_publication_material SHELXTL _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^)+(0.0372P)^2^+0.0925P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.078(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_number_reflns 2381 _refine_ls_number_parameters 205 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.138 _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 Cl1 Cl 0.67458(12) 0.72071(6) 0.39581(4) 0.05302(18) Uani 1 1 d . . . Cl2 Cl 0.34280(8) 0.91446(7) 0.45305(3) 0.04550(16) Uani 1 1 d . . . Cl3 Cl 0.80837(9) 0.94002(7) 0.51288(3) 0.04803(17) Uani 1 1 d . . . O1 O 0.3406(2) 1.06848(15) 0.26251(11) 0.0376(3) Uani 1 1 d . . . O2 O 0.5435(3) 1.25954(18) 0.22656(13) 0.0535(5) Uani 1 1 d . . . O3 O 0.8461(3) 1.20247(16) 0.31945(11) 0.0434(4) Uani 1 1 d . . . O4 O 0.5414(3) 0.74615(17) 0.18024(10) 0.0471(4) Uani 1 1 d . . . O5 O 0.3218(3) 0.81501(19) 0.05866(11) 0.0506(4) Uani 1 1 d . . . O6 O 0.8985(2) 0.94381(16) 0.30239(10) 0.0374(3) Uani 1 1 d . . . H6 H 0.9781 1.0111 0.3002 0.056 Uiso 1 1 calc R . . C1 C 0.4509(4) 1.1817(2) 0.29977(15) 0.0393(5) Uani 1 1 d . . . H1 H 0.3497 1.2347 0.3392 0.047 Uiso 1 1 calc R . . C2 C 0.6593(4) 1.1321(2) 0.35477(14) 0.0347(5) Uani 1 1 d . . . H2 H 0.6427 1.1458 0.4223 0.042 Uiso 1 1 calc R . . C3 C 0.6798(3) 0.9793(2) 0.32945(13) 0.0291(4) Uani 1 1 d . . . C4 C 0.5091(3) 0.9675(2) 0.24531(13) 0.0327(4) Uani 1 1 d . . . H4 H 0.5913 0.9960 0.1894 0.039 Uiso 1 1 calc R . . C5 C 0.3834(4) 0.8390(2) 0.21872(15) 0.0377(5) Uani 1 1 d . . . H5 H 0.3087 0.8005 0.2735 0.045 Uiso 1 1 calc R . . C6 C 0.2095(4) 0.8637(3) 0.13856(16) 0.0501(6) Uani 1 1 d . . . H6A H 0.0698 0.8149 0.1492 0.060 Uiso 1 1 calc R . . H6B H 0.1750 0.9583 0.1323 0.060 Uiso 1 1 calc R . . C7 C 0.4602(4) 0.7066(3) 0.08933(15) 0.0455(5) Uani 1 1 d . . . C8 C 0.6601(6) 0.6966(5) 0.0249(2) 0.0772(10) Uani 1 1 d . . . H8A H 0.6083 0.6714 -0.0366 0.116 Uiso 1 1 calc R . . H8B H 0.7640 0.6301 0.0483 0.116 Uiso 1 1 calc R . . H8C H 0.7355 0.7817 0.0219 0.116 Uiso 1 1 calc R . . C9 C 0.3234(6) 0.5797(3) 0.0960(3) 0.0810(11) Uani 1 1 d . . . H9A H 0.2173 0.5874 0.1463 0.122 Uiso 1 1 calc R . . H9B H 0.4232 0.5054 0.1078 0.122 Uiso 1 1 calc R . . H9C H 0.2423 0.5653 0.0382 0.122 Uiso 1 1 calc R . . C10 C 0.7726(4) 1.2933(2) 0.24602(15) 0.0384(5) Uani 1 1 d . . . C11 C 0.7923(6) 1.4343(3) 0.28330(18) 0.0614(7) Uani 1 1 d . . . H11A H 0.7446 1.4965 0.2357 0.092 Uiso 1 1 calc R . . H11B H 0.9473 1.4521 0.3007 0.092 Uiso 1 1 calc R . . H11C H 0.6976 1.4440 0.3372 0.092 Uiso 1 1 calc R . . C12 C 0.9116(5) 1.2689(4) 0.16012(19) 0.0637(8) Uani 1 1 d . . . H12A H 0.9019 1.1760 0.1430 0.096 Uiso 1 1 calc R . . H12B H 1.0671 1.2919 0.1729 0.096 Uiso 1 1 calc R . . H12C H 0.8546 1.3231 0.1095 0.096 Uiso 1 1 calc R . . C13 C 0.6262(3) 0.8928(2) 0.41730(14) 0.0352(5) 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 Cl1 0.0730(4) 0.0325(3) 0.0535(3) 0.0063(3) -0.0012(3) 0.0059(3) Cl2 0.0355(3) 0.0638(4) 0.0374(2) 0.0018(2) 0.00673(19) -0.0031(3) Cl3 0.0447(3) 0.0651(4) 0.0341(2) 0.0038(3) -0.0095(2) -0.0021(3) O1 0.0335(8) 0.0336(8) 0.0455(8) -0.0040(6) -0.0040(6) 0.0041(6) O2 0.0461(10) 0.0506(10) 0.0634(11) 0.0216(8) -0.0160(8) -0.0058(7) O3 0.0409(9) 0.0376(9) 0.0515(8) 0.0120(7) -0.0125(7) -0.0077(7) O4 0.0548(10) 0.0460(10) 0.0402(8) -0.0139(7) -0.0134(7) 0.0131(7) O5 0.0609(11) 0.0562(11) 0.0345(8) -0.0042(8) -0.0085(7) 0.0115(8) O6 0.0281(7) 0.0412(9) 0.0429(7) -0.0026(7) 0.0057(6) 0.0007(6) C1 0.0387(12) 0.0317(11) 0.0476(11) -0.0028(9) -0.0005(9) 0.0043(8) C2 0.0399(11) 0.0325(11) 0.0315(9) -0.0038(8) -0.0016(8) 0.0002(9) C3 0.0287(10) 0.0304(11) 0.0282(9) -0.0008(8) 0.0014(7) 0.0021(7) C4 0.0346(10) 0.0345(12) 0.0288(9) -0.0013(8) -0.0003(8) 0.0042(8) C5 0.0397(12) 0.0394(13) 0.0340(11) -0.0059(9) -0.0039(9) 0.0011(9) C6 0.0478(13) 0.0557(16) 0.0464(13) -0.0175(11) -0.0126(11) 0.0072(12) C7 0.0529(14) 0.0452(13) 0.0381(10) -0.0142(10) -0.0093(9) 0.0068(11) C8 0.0687(19) 0.110(3) 0.0530(14) -0.0153(18) 0.0034(13) 0.026(2) C9 0.085(2) 0.0527(19) 0.104(3) -0.0125(17) -0.032(2) -0.0091(16) C10 0.0435(12) 0.0346(12) 0.0369(11) 0.0043(9) -0.0089(9) -0.0023(9) C11 0.096(2) 0.0341(13) 0.0538(13) 0.0035(12) -0.0152(14) -0.0052(14) C12 0.0656(17) 0.082(2) 0.0438(13) 0.0011(13) -0.0001(12) 0.0049(15) C13 0.0356(10) 0.0379(12) 0.0320(9) 0.0015(8) -0.0006(8) 0.0016(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 Cl1 C13 1.768(2) . ? Cl2 C13 1.765(2) . ? Cl3 C13 1.789(2) . ? O1 C1 1.405(3) . ? O1 C4 1.438(2) . ? O2 C10 1.416(3) . ? O2 C1 1.416(3) . ? O3 C2 1.404(3) . ? O3 C10 1.448(3) . ? O4 C5 1.428(3) . ? O4 C7 1.433(2) . ? O5 C6 1.411(3) . ? O5 C7 1.421(3) . ? O6 C3 1.395(2) . ? O6 H6 0.8200 . ? C1 C2 1.532(3) . ? C1 H1 0.9800 . ? C2 C3 1.572(3) . ? C2 H2 0.9800 . ? C3 C13 1.558(3) . ? C3 C4 1.562(3) . ? C4 C5 1.527(3) . ? C4 H4 0.9800 . ? C5 C6 1.547(3) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.505(4) . ? C7 C8 1.506(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C12 1.502(4) . ? C10 C11 1.509(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C1 O1 C4 108.11(15) . . ? C10 O2 C1 111.10(17) . . ? C2 O3 C10 110.11(16) . . ? C5 O4 C7 108.31(16) . . ? C6 O5 C7 106.61(17) . . ? C3 O6 H6 109.5 . . ? O1 C1 O2 110.02(18) . . ? O1 C1 C2 107.39(17) . . ? O2 C1 C2 104.03(18) . . ? O1 C1 H1 111.7 . . ? O2 C1 H1 111.7 . . ? C2 C1 H1 111.7 . . ? O3 C2 C1 106.33(16) . . ? O3 C2 C3 109.91(17) . . ? C1 C2 C3 104.99(16) . . ? O3 C2 H2 111.8 . . ? C1 C2 H2 111.8 . . ? C3 C2 H2 111.8 . . ? O6 C3 C13 106.16(15) . . ? O6 C3 C4 110.90(15) . . ? C13 C3 C4 116.27(16) . . ? O6 C3 C2 112.54(17) . . ? C13 C3 C2 109.64(16) . . ? C4 C3 C2 101.50(15) . . ? O1 C4 C5 107.30(16) . . ? O1 C4 C3 104.82(15) . . ? C5 C4 C3 124.10(16) . . ? O1 C4 H4 106.5 . . ? C5 C4 H4 106.5 . . ? C3 C4 H4 106.5 . . ? O4 C5 C4 108.93(17) . . ? O4 C5 C6 104.37(16) . . ? C4 C5 C6 111.43(18) . . ? O4 C5 H5 110.6 . . ? C4 C5 H5 110.6 . . ? C6 C5 H5 110.6 . . ? O5 C6 C5 103.31(18) . . ? O5 C6 H6A 111.1 . . ? C5 C6 H6A 111.1 . . ? O5 C6 H6B 111.1 . . ? C5 C6 H6B 111.1 . . ? H6A C6 H6B 109.1 . . ? O5 C7 O4 104.72(18) . . ? O5 C7 C9 110.8(2) . . ? O4 C7 C9 110.4(2) . . ? O5 C7 C8 108.2(2) . . ? O4 C7 C8 108.4(2) . . ? C9 C7 C8 113.9(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 O3 105.66(17) . . ? O2 C10 C12 109.2(2) . . ? O3 C10 C12 109.1(2) . . ? O2 C10 C11 111.1(2) . . ? O3 C10 C11 107.90(17) . . ? C12 C10 C11 113.5(2) . . ? 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 . . ? C3 C13 Cl2 111.44(13) . . ? C3 C13 Cl1 111.36(14) . . ? Cl2 C13 Cl1 108.91(12) . . ? C3 C13 Cl3 110.02(14) . . ? Cl2 C13 Cl3 107.98(11) . . ? Cl1 C13 Cl3 106.96(11) . . ? 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 C4 O1 C1 O2 82.3(2) . . . . ? C4 O1 C1 C2 -30.3(2) . . . . ? C10 O2 C1 O1 -131.28(19) . . . . ? C10 O2 C1 C2 -16.5(2) . . . . ? C10 O3 C2 C1 0.0(2) . . . . ? C10 O3 C2 C3 113.12(18) . . . . ? O1 C1 C2 O3 126.42(18) . . . . ? O2 C1 C2 O3 9.8(2) . . . . ? O1 C1 C2 C3 9.9(2) . . . . ? O2 C1 C2 C3 -106.68(19) . . . . ? O3 C2 C3 O6 16.4(2) . . . . ? C1 C2 C3 O6 130.41(17) . . . . ? O3 C2 C3 C13 134.32(16) . . . . ? C1 C2 C3 C13 -111.69(18) . . . . ? O3 C2 C3 C4 -102.17(17) . . . . ? C1 C2 C3 C4 11.8(2) . . . . ? C1 O1 C4 C5 171.80(16) . . . . ? C1 O1 C4 C3 38.2(2) . . . . ? O6 C3 C4 O1 -149.19(17) . . . . ? C13 C3 C4 O1 89.44(19) . . . . ? C2 C3 C4 O1 -29.43(19) . . . . ? O6 C3 C4 C5 87.4(2) . . . . ? C13 C3 C4 C5 -34.0(3) . . . . ? C2 C3 C4 C5 -152.85(19) . . . . ? C7 O4 C5 C4 -124.64(19) . . . . ? C7 O4 C5 C6 -5.5(2) . . . . ? O1 C4 C5 O4 166.63(15) . . . . ? C3 C4 C5 O4 -71.1(2) . . . . ? O1 C4 C5 C6 52.0(2) . . . . ? C3 C4 C5 C6 174.32(18) . . . . ? C7 O5 C6 C5 32.3(2) . . . . ? O4 C5 C6 O5 -16.2(2) . . . . ? C4 C5 C6 O5 101.2(2) . . . . ? C6 O5 C7 O4 -36.6(2) . . . . ? C6 O5 C7 C9 82.4(3) . . . . ? C6 O5 C7 C8 -152.1(2) . . . . ? C5 O4 C7 O5 25.3(2) . . . . ? C5 O4 C7 C9 -93.9(3) . . . . ? C5 O4 C7 C8 140.7(3) . . . . ? C1 O2 C10 O3 16.8(3) . . . . ? C1 O2 C10 C12 134.1(2) . . . . ? C1 O2 C10 C11 -100.0(2) . . . . ? C2 O3 C10 O2 -9.9(2) . . . . ? C2 O3 C10 C12 -127.2(2) . . . . ? C2 O3 C10 C11 109.1(2) . . . . ? O6 C3 C13 Cl2 -174.13(13) . . . . ? C4 C3 C13 Cl2 -50.3(2) . . . . ? C2 C3 C13 Cl2 64.06(19) . . . . ? O6 C3 C13 Cl1 -52.29(18) . . . . ? C4 C3 C13 Cl1 71.56(19) . . . . ? C2 C3 C13 Cl1 -174.09(13) . . . . ? O6 C3 C13 Cl3 66.13(18) . . . . ? C4 C3 C13 Cl3 -170.01(13) . . . . ? C2 C3 C13 Cl3 -55.67(19) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.312 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 936034' ####################################################################### # # 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_C20H26N4O6compound3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Sugar _chemical_melting_point '146-148degree centigrade' _chemical_formula_moiety 'C20 H26 N4 O6' _chemical_formula_sum 'C20 H26 N4 O6' _chemical_formula_weight 418.45 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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.7965(6) _cell_length_b 10.6180(7) _cell_length_c 21.199(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2205.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3358 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 21.74 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9733 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11224 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3887 _reflns_number_gt 3283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, PyMOL and PLATON' _computing_publication_material SHELXTL _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^)+(0.0539P)^2^+0.2283P] 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 riding _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 -0.7(14) _refine_ls_number_reflns 3887 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.57027(18) -0.04577(16) 0.87501(7) 0.0618(5) Uani 1 1 d . A . O2 O 0.6075(13) 0.098(2) 0.8022(8) 0.082(4) Uani 0.40 1 d P A 1 O2' O 0.5509(9) 0.1098(12) 0.7943(5) 0.079(2) Uani 0.60 1 d P A 2 O3 O 0.5748(2) 0.25127(16) 0.87261(7) 0.0691(5) Uani 1 1 d . A . O4 O 0.6947(2) -0.06947(16) 1.03416(8) 0.0724(5) Uani 1 1 d . A . O5 O 0.8673(2) -0.1868(2) 0.99895(10) 0.0983(7) Uani 1 1 d . A . O6 O 0.72723(14) 0.21312(15) 0.99834(8) 0.0575(4) Uani 1 1 d . . . N1 N 0.40972(18) 0.04476(17) 0.98418(9) 0.0475(4) Uani 1 1 d . A . N2 N 0.4119(2) 0.01809(19) 1.04029(10) 0.0562(5) Uani 1 1 d . . . N3 N 0.3978(3) -0.0102(3) 1.09078(12) 0.0950(9) Uani 1 1 d . . . N4 N 0.51782(16) 0.27689(16) 1.02864(8) 0.0448(4) Uani 1 1 d . . . H4 H 0.4315 0.2627 1.0268 0.054 Uiso 1 1 calc R . . C1 C 0.4983(3) 0.0526(2) 0.84600(11) 0.0602(7) Uani 1 1 d . . . H1 H 0.4132 0.0272 0.8253 0.072 Uiso 1 1 calc R A 1 C2 C 0.4834(2) 0.1585(2) 0.89345(10) 0.0497(5) Uani 1 1 d . A . H2 H 0.3895 0.1896 0.8964 0.060 Uiso 1 1 calc R . . C3 C 0.53452(19) 0.10159(19) 0.95604(9) 0.0393(5) Uani 1 1 d . . . C4 C 0.6322(2) -0.0005(2) 0.93180(10) 0.0474(5) Uani 1 1 d . A . H4A H 0.7209 0.0374 0.9219 0.057 Uiso 1 1 calc R . . C5 C 0.6526(3) -0.1127(2) 0.97421(11) 0.0575(6) Uani 1 1 d . . . H5 H 0.5672 -0.1602 0.9780 0.069 Uiso 1 1 calc R A . C6 C 0.7678(3) -0.1999(3) 0.95291(15) 0.0837(9) Uani 1 1 d . A . H6A H 0.7364 -0.2864 0.9504 0.100 Uiso 1 1 calc R . . H6B H 0.8025 -0.1747 0.9120 0.100 Uiso 1 1 calc R . . C7 C 0.8019(3) -0.1473(3) 1.05484(13) 0.0772(8) Uani 1 1 d . . . C8 C 0.9007(5) -0.0685(5) 1.0933(2) 0.1314(16) Uani 1 1 d . A . H8A H 0.8564 -0.0401 1.1311 0.197 Uiso 1 1 calc R . . H8B H 0.9295 0.0029 1.0689 0.197 Uiso 1 1 calc R . . H8C H 0.9789 -0.1186 1.1042 0.197 Uiso 1 1 calc R . . C9 C 0.7443(5) -0.2568(3) 1.09111(18) 0.1202(15) Uani 1 1 d . A . H9A H 0.6836 -0.3038 1.0645 0.180 Uiso 1 1 calc R . . H9B H 0.6951 -0.2262 1.1272 0.180 Uiso 1 1 calc R . . H9C H 0.8174 -0.3104 1.1049 0.180 Uiso 1 1 calc R . . C10 C 0.6089(3) 0.2290(3) 0.80878(12) 0.0665(7) Uani 1 1 d . . . C11 C 0.5299(5) 0.3137(5) 0.76654(16) 0.1314(17) Uani 1 1 d . A . H11A H 0.4340 0.2984 0.7721 0.197 Uiso 1 1 calc R . . H11B H 0.5547 0.2977 0.7235 0.197 Uiso 1 1 calc R . . H11C H 0.5498 0.3998 0.7768 0.197 Uiso 1 1 calc R . . C12 C 0.7592(4) 0.2435(8) 0.8007(2) 0.166(2) Uani 1 1 d . A . H12A H 0.7802 0.2525 0.7567 0.248 Uiso 1 1 calc R . . H12B H 0.8046 0.1704 0.8171 0.248 Uiso 1 1 calc R . . H12C H 0.7895 0.3169 0.8232 0.19(3) Uiso 1 1 calc R . . C13 C 0.60284(19) 0.20216(19) 0.99666(9) 0.0407(5) Uani 1 1 d . A . C14 C 0.5674(2) 0.3818(2) 1.06656(11) 0.0556(6) Uani 1 1 d . . . H14A H 0.5028 0.4507 1.0632 0.067 Uiso 1 1 calc R . . H14B H 0.6535 0.4105 1.0491 0.067 Uiso 1 1 calc R . . C15 C 0.5880(3) 0.3517(3) 1.13475(12) 0.0623(7) Uani 1 1 d . . . C16 C 0.5741(4) 0.4466(4) 1.17905(16) 0.1000(11) Uani 1 1 d . . . H16 H 0.5512 0.5276 1.1661 0.120 Uiso 1 1 calc R . . C17 C 0.5938(6) 0.4221(7) 1.2422(2) 0.1329(18) Uani 1 1 d . . . H17 H 0.5815 0.4861 1.2716 0.159 Uiso 1 1 calc R . . C18 C 0.6306(5) 0.3064(7) 1.26190(17) 0.1321(18) Uani 1 1 d . . . H18 H 0.6460 0.2912 1.3045 0.159 Uiso 1 1 calc R . . C19 C 0.6453(4) 0.2107(5) 1.21860(17) 0.1087(12) Uani 1 1 d . . . H19 H 0.6690 0.1303 1.2320 0.130 Uiso 1 1 calc R . . C20 C 0.6246(3) 0.2343(3) 1.15485(13) 0.0752(8) Uani 1 1 d . . . H20 H 0.6358 0.1697 1.1257 0.090 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 0.0801(11) 0.0544(9) 0.0509(9) -0.0137(8) -0.0085(9) 0.0072(9) O2 0.108(9) 0.082(5) 0.057(7) 0.002(5) 0.024(6) 0.013(7) O2' 0.124(7) 0.072(4) 0.041(2) 0.003(2) 0.006(4) -0.006(5) O3 0.0999(13) 0.0556(10) 0.0518(9) 0.0049(8) 0.0051(9) -0.0178(10) O4 0.0988(14) 0.0598(11) 0.0587(10) -0.0034(9) -0.0169(9) 0.0312(10) O5 0.0863(14) 0.1199(18) 0.0885(14) 0.0041(14) -0.0009(12) 0.0429(13) O6 0.0326(8) 0.0600(10) 0.0800(11) -0.0163(9) 0.0023(7) -0.0038(7) N1 0.0420(9) 0.0483(10) 0.0522(11) -0.0023(9) -0.0009(8) -0.0059(8) N2 0.0578(12) 0.0538(12) 0.0570(13) 0.0003(10) 0.0042(10) -0.0172(10) N3 0.113(2) 0.109(2) 0.0632(15) 0.0160(15) 0.0135(14) -0.0434(18) N4 0.0320(8) 0.0467(10) 0.0556(11) -0.0123(9) 0.0008(8) -0.0023(8) C1 0.0744(17) 0.0558(15) 0.0504(14) -0.0002(12) -0.0135(13) -0.0095(14) C2 0.0481(12) 0.0474(13) 0.0538(13) 0.0066(11) -0.0032(10) 0.0006(11) C3 0.0367(10) 0.0380(10) 0.0432(11) 0.0001(9) -0.0004(9) 0.0001(9) C4 0.0473(12) 0.0460(12) 0.0488(12) -0.0058(10) -0.0016(10) 0.0015(10) C5 0.0662(15) 0.0452(13) 0.0613(15) -0.0037(12) -0.0037(12) 0.0139(11) C6 0.102(2) 0.0631(17) 0.086(2) -0.0115(15) -0.0152(18) 0.0380(17) C7 0.087(2) 0.0774(19) 0.0668(17) 0.0136(15) -0.0034(16) 0.0239(17) C8 0.119(3) 0.171(4) 0.104(3) -0.008(3) -0.041(3) -0.008(3) C9 0.177(4) 0.081(2) 0.102(3) 0.033(2) 0.012(3) 0.032(3) C10 0.0756(17) 0.0677(19) 0.0563(15) 0.0135(13) 0.0055(13) -0.0016(15) C11 0.183(4) 0.141(4) 0.071(2) 0.040(2) 0.005(2) 0.053(3) C12 0.087(3) 0.276(7) 0.133(4) 0.017(5) 0.019(3) -0.041(4) C13 0.0335(10) 0.0403(11) 0.0482(11) 0.0014(10) 0.0013(9) -0.0010(8) C14 0.0460(12) 0.0473(13) 0.0736(16) -0.0155(12) 0.0023(11) -0.0011(11) C15 0.0483(13) 0.0759(18) 0.0627(15) -0.0186(14) 0.0043(12) -0.0121(14) C16 0.111(3) 0.105(3) 0.084(2) -0.0421(19) 0.0153(19) -0.030(2) C17 0.159(4) 0.168(5) 0.072(3) -0.050(3) 0.005(3) -0.034(4) C18 0.152(4) 0.189(5) 0.055(2) -0.020(3) -0.013(2) -0.032(4) C19 0.108(3) 0.142(3) 0.076(2) 0.012(2) -0.0137(19) -0.021(3) C20 0.0651(17) 0.100(2) 0.0605(16) -0.0108(16) -0.0048(13) -0.0106(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.402(3) . ? O1 C4 1.432(3) . ? O2 C10 1.40(2) . ? O2 C1 1.495(18) . ? O2' C1 1.356(12) . ? O2' C10 1.421(13) . ? O3 C2 1.403(3) . ? O3 C10 1.414(3) . ? O4 C7 1.406(3) . ? O4 C5 1.413(3) . ? O5 C6 1.386(4) . ? O5 C7 1.411(3) . ? O6 C13 1.225(2) . ? N1 N2 1.223(3) . ? N1 C3 1.488(3) . ? N2 N3 1.120(3) . ? N4 C13 1.335(3) . ? N4 C14 1.457(3) . ? N4 H4 0.8600 . ? C1 C2 1.516(3) . ? C1 H1 0.9800 . ? C2 C3 1.541(3) . ? C2 H2 0.9800 . ? C3 C13 1.526(3) . ? C3 C4 1.534(3) . ? C4 C5 1.507(3) . ? C4 H4A 0.9800 . ? C5 C6 1.527(4) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C9 1.504(5) . ? C7 C8 1.517(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.487(4) . ? C10 C12 1.490(5) . ? 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 1.494(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.365(4) . ? C15 C16 1.384(4) . ? C16 C17 1.378(6) . ? C16 H16 0.9300 . ? C17 C18 1.347(7) . ? C17 H17 0.9300 . ? C18 C19 1.376(7) . ? C18 H18 0.9300 . ? C19 C20 1.389(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 C1 O1 C4 109.37(17) . . ? C10 O2 C1 105.4(11) . . ? C1 O2' C10 112.1(8) . . ? C2 O3 C10 109.55(19) . . ? C7 O4 C5 107.89(19) . . ? C6 O5 C7 107.6(2) . . ? N2 N1 C3 118.02(18) . . ? N3 N2 N1 171.6(3) . . ? C13 N4 C14 121.76(17) . . ? C13 N4 H4 119.1 . . ? C14 N4 H4 119.1 . . ? O2' C1 O1 119.8(4) . . ? O2' C1 O2 23.3(6) . . ? O1 C1 O2 98.7(6) . . ? O2' C1 C2 103.9(6) . . ? O1 C1 C2 108.05(18) . . ? O2 C1 C2 104.1(8) . . ? O2' C1 H1 94.9 . . ? O1 C1 H1 114.8 . . ? O2 C1 H1 114.8 . . ? C2 C1 H1 114.8 . . ? O3 C2 C1 104.52(18) . . ? O3 C2 C3 109.83(18) . . ? C1 C2 C3 104.43(18) . . ? O3 C2 H2 112.5 . . ? C1 C2 H2 112.5 . . ? C3 C2 H2 112.5 . . ? N1 C3 C13 114.69(16) . . ? N1 C3 C4 111.13(17) . . ? C13 C3 C4 114.17(16) . . ? N1 C3 C2 103.73(16) . . ? C13 C3 C2 110.72(17) . . ? C4 C3 C2 101.01(16) . . ? O1 C4 C5 106.98(18) . . ? O1 C4 C3 104.74(17) . . ? C5 C4 C3 116.22(18) . . ? O1 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? O4 C5 C4 108.55(18) . . ? O4 C5 C6 104.3(2) . . ? C4 C5 C6 113.7(2) . . ? O4 C5 H5 110.0 . . ? C4 C5 H5 110.0 . . ? C6 C5 H5 110.0 . . ? O5 C6 C5 104.5(2) . . ? O5 C6 H6A 110.9 . . ? C5 C6 H6A 110.9 . . ? O5 C6 H6B 110.9 . . ? C5 C6 H6B 110.9 . . ? H6A C6 H6B 108.9 . . ? O4 C7 O5 104.6(2) . . ? O4 C7 C9 109.5(3) . . ? O5 C7 C9 111.7(3) . . ? O4 C7 C8 108.7(3) . . ? O5 C7 C8 109.0(3) . . ? C9 C7 C8 113.0(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 O3 105.0(7) . . ? O2 C10 O2' 24.2(6) . . ? O3 C10 O2' 105.2(5) . . ? O2 C10 C11 122.5(6) . . ? O3 C10 C11 110.6(3) . . ? O2' C10 C11 101.6(4) . . ? O2 C10 C12 95.8(7) . . ? O3 C10 C12 109.0(3) . . ? O2' C10 C12 117.5(5) . . ? C11 C10 C12 112.5(4) . . ? 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 . . ? O6 C13 N4 123.33(19) . . ? O6 C13 C3 121.28(18) . . ? N4 C13 C3 115.39(16) . . ? N4 C14 C15 114.5(2) . . ? N4 C14 H14A 108.6 . . ? C15 C14 H14A 108.6 . . ? N4 C14 H14B 108.6 . . ? C15 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C20 C15 C16 118.6(3) . . ? C20 C15 C14 122.2(2) . . ? C16 C15 C14 119.2(3) . . ? C17 C16 C15 120.6(5) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.7(4) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 119.7(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C20 120.0(5) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C15 C20 C19 120.4(3) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? 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 C3 N1 N2 N3 175.8(19) . . . . ? C10 O2' C1 O1 -103.0(6) . . . . ? C10 O2' C1 O2 -76(3) . . . . ? C10 O2' C1 C2 17.7(6) . . . . ? C4 O1 C1 O2' 104.4(6) . . . . ? C4 O1 C1 O2 93.7(8) . . . . ? C4 O1 C1 C2 -14.2(3) . . . . ? C10 O2 C1 O2' 71(3) . . . . ? C10 O2 C1 O1 -133.2(6) . . . . ? C10 O2 C1 C2 -22.0(8) . . . . ? C10 O3 C2 C1 18.3(3) . . . . ? C10 O3 C2 C3 129.8(2) . . . . ? O2' C1 C2 O3 -21.7(4) . . . . ? O1 C1 C2 O3 106.6(2) . . . . ? O2 C1 C2 O3 2.3(5) . . . . ? O2' C1 C2 C3 -137.1(4) . . . . ? O1 C1 C2 C3 -8.8(3) . . . . ? O2 C1 C2 C3 -113.0(5) . . . . ? N2 N1 C3 C13 -42.6(3) . . . . ? N2 N1 C3 C4 88.8(2) . . . . ? N2 N1 C3 C2 -163.47(19) . . . . ? O3 C2 C3 N1 159.31(17) . . . . ? C1 C2 C3 N1 -89.1(2) . . . . ? O3 C2 C3 C13 35.8(2) . . . . ? C1 C2 C3 C13 147.40(19) . . . . ? O3 C2 C3 C4 -85.5(2) . . . . ? C1 C2 C3 C4 26.1(2) . . . . ? C1 O1 C4 C5 155.5(2) . . . . ? C1 O1 C4 C3 31.6(2) . . . . ? N1 C3 C4 O1 74.6(2) . . . . ? C13 C3 C4 O1 -153.76(17) . . . . ? C2 C3 C4 O1 -34.9(2) . . . . ? N1 C3 C4 C5 -43.2(2) . . . . ? C13 C3 C4 C5 88.5(2) . . . . ? C2 C3 C4 C5 -152.69(19) . . . . ? C7 O4 C5 C4 -136.3(2) . . . . ? C7 O4 C5 C6 -14.8(3) . . . . ? O1 C4 C5 O4 -171.43(19) . . . . ? C3 C4 C5 O4 -54.9(3) . . . . ? O1 C4 C5 C6 73.0(3) . . . . ? C3 C4 C5 C6 -170.5(2) . . . . ? C7 O5 C6 C5 24.6(3) . . . . ? O4 C5 C6 O5 -6.0(3) . . . . ? C4 C5 C6 O5 112.1(3) . . . . ? C5 O4 C7 O5 30.1(3) . . . . ? C5 O4 C7 C9 -89.8(3) . . . . ? C5 O4 C7 C8 146.4(3) . . . . ? C6 O5 C7 O4 -34.4(3) . . . . ? C6 O5 C7 C9 84.0(3) . . . . ? C6 O5 C7 C8 -150.4(3) . . . . ? C1 O2 C10 O3 33.3(8) . . . . ? C1 O2 C10 O2' -60(2) . . . . ? C1 O2 C10 C11 -93.8(9) . . . . ? C1 O2 C10 C12 144.8(7) . . . . ? C2 O3 C10 O2 -33.3(6) . . . . ? C2 O3 C10 O2' -8.1(4) . . . . ? C2 O3 C10 C11 100.8(3) . . . . ? C2 O3 C10 C12 -135.0(4) . . . . ? C1 O2' C10 O2 86(3) . . . . ? C1 O2' C10 O3 -7.0(6) . . . . ? C1 O2' C10 C11 -122.3(5) . . . . ? C1 O2' C10 C12 114.5(6) . . . . ? C14 N4 C13 O6 2.5(3) . . . . ? C14 N4 C13 C3 -176.41(18) . . . . ? N1 C3 C13 O6 143.9(2) . . . . ? C4 C3 C13 O6 14.0(3) . . . . ? C2 C3 C13 O6 -99.2(2) . . . . ? N1 C3 C13 N4 -37.2(2) . . . . ? C4 C3 C13 N4 -167.05(18) . . . . ? C2 C3 C13 N4 79.8(2) . . . . ? C13 N4 C14 C15 -94.5(2) . . . . ? N4 C14 C15 C20 31.1(3) . . . . ? N4 C14 C15 C16 -151.1(3) . . . . ? C20 C15 C16 C17 -1.4(5) . . . . ? C14 C15 C16 C17 -179.4(3) . . . . ? C15 C16 C17 C18 1.8(8) . . . . ? C16 C17 C18 C19 -1.7(9) . . . . ? C17 C18 C19 C20 1.2(7) . . . . ? C16 C15 C20 C19 1.0(4) . . . . ? C14 C15 C20 C19 178.8(3) . . . . ? C18 C19 C20 C15 -0.8(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.153 _refine_diff_density_min -0.115 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 936035'