# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland ; _publ_contact_author_email gabro@ch.pw.edu.pl _publ_contact_author_name 'Karolina Tomczyk' loop_ _publ_author_name K.Tomczyk P.Gunka P.Parzuchowski J.Zachara G.Rokicki data_comp15 _database_code_depnum_ccdc_archive 'CCDC 868593' #TrackingRef '- Comp_15_20.cif' _audit_creation_date 2012-01-22 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 2,4,7-trioxa-3-oxy-bicyclo[3.3.0]octane ; _chemical_formula_moiety 'C5 H6 O4' _chemical_formula_sum 'C5 H6 O4' _chemical_formula_weight 130.10 _chemical_absolute_configuration ad _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 0.0181 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' O O 0.0492 0.0322 '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' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _cell_length_a 4.25566(10) _cell_length_b 10.2167(2) _cell_length_c 12.2711(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 533.53(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6224 _cell_measurement_temperature 100 _cell_measurement_theta_max 66.8895 _cell_measurement_theta_min 3.5989 _exptl_absorpt_coefficient_mu 1.252 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61950 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0111 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7552 _diffrn_reflns_theta_full 67.00 _diffrn_reflns_theta_max 67.00 _diffrn_reflns_theta_min 5.63 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 10.3347 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -97.00 -21.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -40.9488 125.0000 -90.0000 76 #__ type_ start__ end____ width___ exp.time_ 2 omega -26.00 67.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 40.9488 -37.0000 -30.0000 93 #__ type_ start__ end____ width___ exp.time_ 3 omega 17.00 113.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 40.9488 37.0000 150.0000 96 #__ type_ start__ end____ width___ exp.time_ 4 omega 9.00 35.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -92.0000 51.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 30.00 69.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -45.0000 120.0000 39 #__ type_ start__ end____ width___ exp.time_ 6 omega 68.00 152.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 45.0000 -30.0000 84 #__ type_ start__ end____ width___ exp.time_ 7 omega 137.00 163.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 125.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 74.00 113.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 125.0000 30.0000 39 #__ type_ start__ end____ width___ exp.time_ 9 omega 52.00 77.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -45.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 10 omega 19.00 74.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -45.0000 -30.0000 55 #__ type_ start__ end____ width___ exp.time_ 11 omega 119.00 147.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 125.0000 -90.0000 28 #__ type_ start__ end____ width___ exp.time_ 12 omega 40.00 89.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -77.0000 -30.0000 49 #__ type_ start__ end____ width___ exp.time_ 13 omega 32.00 126.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 15.0000 150.0000 94 #__ type_ start__ end____ width___ exp.time_ 14 omega 60.00 86.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -77.0000 90.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega 98.00 126.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -77.0000 90.0000 28 #__ type_ start__ end____ width___ exp.time_ 16 omega 11.00 117.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -15.0000 150.0000 106 #__ type_ start__ end____ width___ exp.time_ 17 omega 121.00 154.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -15.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 18 omega 47.00 132.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -92.0000 51.0000 85 #__ type_ start__ end____ width___ exp.time_ 19 omega 73.00 99.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -88.0000 -106.0000 26 #__ type_ start__ end____ width___ exp.time_ 20 omega 126.00 151.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 125.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 21 omega 67.00 96.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 77.0000 90.0000 29 #__ type_ start__ end____ width___ exp.time_ 22 omega 32.00 132.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 -90.0000 -140.0000 100 #__ type_ start__ end____ width___ exp.time_ 23 omega 7.00 120.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 40.9488 77.0000 30.0000 113 #__ type_ start__ end____ width___ exp.time_ 24 omega 7.00 120.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 40.9488 77.0000 -180.0000 113 #__ type_ start__ end____ width___ exp.time_ 25 omega 7.00 120.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 40.9488 77.0000 -90.0000 113 #__ type_ start__ end____ width___ exp.time_ 26 omega -35.00 67.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 40.9488 -37.0000 60.0000 102 #__ type_ start__ end____ width___ exp.time_ 27 omega -121.00 -42.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 125.0000 0.0000 79 #__ type_ start__ end____ width___ exp.time_ 28 omega -166.00 -58.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 -71.0000 -177.0000 108 #__ type_ start__ end____ width___ exp.time_ 29 omega -169.00 -56.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -90.0000 -77.0000 150.0000 113 #__ type_ start__ end____ width___ exp.time_ 30 omega 60.00 172.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 77.0000 0.0000 112 #__ type_ start__ end____ width___ exp.time_ 31 omega 66.00 168.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 45.0000 -120.0000 102 #__ type_ start__ end____ width___ exp.time_ 32 omega 60.00 172.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 93.5000 77.0000 -90.0000 112 ; _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0245235000 _diffrn_orient_matrix_UB_12 -0.1465017000 _diffrn_orient_matrix_UB_13 -0.0284914000 _diffrn_orient_matrix_UB_21 0.1168805000 _diffrn_orient_matrix_UB_22 -0.0357042000 _diffrn_orient_matrix_UB_23 0.1150441000 _diffrn_orient_matrix_UB_31 -0.3417344000 _diffrn_orient_matrix_UB_32 -0.0016977000 _diffrn_orient_matrix_UB_33 0.0413815000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 913 _reflns_number_total 945 _reflns_threshold_expression I>2u(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _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 ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.145 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack H D (1983), Acta Cryst. A39, 876-881. 356 Friedel pairs ; _refine_ls_abs_structure_Flack 0.13(19) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 88 _refine_ls_number_reflns 945 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0225 _refine_ls_restrained_S_all 1.062 _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^)+(0.0353P)^2^+0.1007P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.0587 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _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 0.3772(2) 0.26503(9) 0.27725(8) 0.0291(3) Uani 1 1 d . . . O2 O 0.0637(2) 0.31422(8) 0.41782(7) 0.0211(2) Uani 1 1 d . . . O3 O 0.0897(2) 0.44926(9) 0.27642(6) 0.0209(2) Uani 1 1 d . . . O4 O 0.2378(2) 0.58694(8) 0.48715(7) 0.0227(2) Uani 1 1 d . . . C1 C 0.1914(3) 0.33649(12) 0.31995(11) 0.0200(3) Uani 1 1 d . . . C2 C -0.1300(3) 0.42376(12) 0.45099(9) 0.0186(3) Uani 1 1 d . . . H2 H -0.336(4) 0.3920(15) 0.4684(11) 0.022 Uiso 1 1 d . . . C3 C 0.0285(3) 0.49908(13) 0.54196(10) 0.0227(3) Uani 1 1 d . . . H3A H -0.1279 0.5480 0.5857 0.027 Uiso 1 1 calc R . . H3B H 0.1459 0.4393 0.5907 0.027 Uiso 1 1 calc R . . C4 C 0.0540(3) 0.63671(12) 0.39803(11) 0.0210(3) Uani 1 1 d . . . H4A H 0.1904 0.6772 0.3421 0.025 Uiso 1 1 calc R . . H4B H -0.0994 0.7026 0.4238 0.025 Uiso 1 1 calc R . . C5 C -0.1123(3) 0.51737(12) 0.35290(10) 0.0173(3) Uani 1 1 d . . . H5 H -0.308(4) 0.5361(14) 0.3179(12) 0.021 Uiso 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 O1 0.0269(5) 0.0281(5) 0.0323(5) -0.0120(4) -0.0011(4) 0.0060(4) O2 0.0222(5) 0.0178(4) 0.0235(5) 0.0012(4) -0.0010(4) 0.0023(3) O3 0.0233(5) 0.0209(4) 0.0184(4) -0.0010(3) 0.0023(4) 0.0013(4) O4 0.0211(5) 0.0229(5) 0.0240(4) -0.0030(4) -0.0027(4) -0.0022(4) C1 0.0186(6) 0.0197(6) 0.0216(6) -0.0039(5) -0.0032(5) -0.0029(5) C2 0.0160(6) 0.0191(6) 0.0208(6) 0.0019(5) 0.0010(5) 0.0013(5) C3 0.0244(7) 0.0255(7) 0.0182(6) -0.0013(5) 0.0011(5) 0.0001(5) C4 0.0210(6) 0.0185(6) 0.0234(6) 0.0015(5) 0.0017(6) 0.0004(5) C5 0.0147(6) 0.0188(6) 0.0185(6) 0.0005(4) 0.0011(5) 0.0011(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 C1 1.1969(16) . ? O2 C1 1.3379(16) . ? O2 C2 1.4483(15) . ? O3 C1 1.3417(16) . ? O3 C5 1.4504(15) . ? O4 C3 1.4323(16) . ? O4 C4 1.4376(16) . ? C2 H2 0.960(17) . ? C2 C3 1.5145(18) . ? C2 C5 1.5391(17) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.5146(18) . ? C5 H5 0.956(17) . ? 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 O2 C2 110.62(9) . . ? C1 O3 C5 110.22(9) . . ? C3 O4 C4 103.91(9) . . ? O1 C1 O2 123.90(12) . . ? O1 C1 O3 124.24(12) . . ? O2 C1 O3 111.85(10) . . ? O2 C2 H2 108.7(9) . . ? O2 C2 C3 110.26(10) . . ? O2 C2 C5 103.44(9) . . ? C3 C2 H2 114.5(9) . . ? C3 C2 C5 103.82(10) . . ? C5 C2 H2 115.4(9) . . ? O4 C3 C2 104.44(9) . . ? O4 C3 H3A 110.9 . . ? O4 C3 H3B 110.9 . . ? C2 C3 H3A 110.9 . . ? C2 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? O4 C4 H4A 110.9 . . ? O4 C4 H4B 110.9 . . ? O4 C4 C5 104.34(10) . . ? H4A C4 H4B 108.9 . . ? C5 C4 H4A 110.9 . . ? C5 C4 H4B 110.9 . . ? O3 C5 C2 103.71(9) . . ? O3 C5 C4 110.25(10) . . ? O3 C5 H5 108.7(9) . . ? C2 C5 H5 115.6(9) . . ? C4 C5 C2 103.72(10) . . ? C4 C5 H5 114.2(9) . . ? 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 O2 C2 C3 O4 84.45(11) . . . . ? O2 C2 C5 O3 -0.08(12) . . . . ? O2 C2 C5 C4 -115.30(10) . . . . ? O4 C4 C5 O3 -84.59(11) . . . . ? O4 C4 C5 C2 25.90(12) . . . . ? C1 O2 C2 C3 -108.07(11) . . . . ? C1 O2 C2 C5 2.42(13) . . . . ? C1 O3 C5 C2 -2.28(13) . . . . ? C1 O3 C5 C4 108.22(11) . . . . ? C2 O2 C1 O1 174.98(12) . . . . ? C2 O2 C1 O3 -4.11(13) . . . . ? C3 O4 C4 C5 -43.44(12) . . . . ? C3 C2 C5 O3 115.10(11) . . . . ? C3 C2 C5 C4 -0.13(13) . . . . ? C4 O4 C3 C2 43.36(12) . . . . ? C5 O3 C1 O1 -175.05(12) . . . . ? C5 O3 C1 O2 4.04(13) . . . . ? C5 C2 C3 O4 -25.80(13) . . . . ? #====END data_comp20 _database_code_depnum_ccdc_archive 'CCDC 868594' #TrackingRef '- Comp_15_20.cif' _audit_creation_date 2012-01-19 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; 6-(1,3-dioxolan-2-one-4-yl)-2,4,7-trioxa-3-oxy-bicyclo[3.3.0]octane ; _chemical_formula_moiety 'C8 H8 O7' _chemical_formula_sum 'C8 H8 O7' _chemical_formula_weight 216.14 _chemical_absolute_configuration syn _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 0.0000 '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 0.0000 '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' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _cell_length_a 7.9412(2) _cell_length_b 10.0129(3) _cell_length_c 10.8310(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 861.22(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4403 _cell_measurement_temperature 100 _cell_measurement_theta_max 29.4573 _cell_measurement_theta_min 3.2676 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86045 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 448 _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 11362 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 29.52 _diffrn_reflns_theta_min 3.27 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 10.3347 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.947 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -15.00 68.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -11.4008 19.0000 90.0000 83 #__ type_ start__ end____ width___ exp.time_ 2 omega -15.00 40.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 11.7133 19.0000 30.0000 55 #__ type_ start__ end____ width___ exp.time_ 3 omega -31.00 24.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 11.7133 100.0000 96.0000 55 #__ type_ start__ end____ width___ exp.time_ 4 omega -64.00 38.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 11.7133 -38.0000 150.0000 102 #__ type_ start__ end____ width___ exp.time_ 5 omega -62.00 38.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 11.7133 -60.0000 -4.0000 100 #__ type_ start__ end____ width___ exp.time_ 6 omega -62.00 41.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 11.7133 -57.0000 -90.0000 103 ; _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0267267000 _diffrn_orient_matrix_UB_12 -0.0473596000 _diffrn_orient_matrix_UB_13 -0.0445899000 _diffrn_orient_matrix_UB_21 0.0570905000 _diffrn_orient_matrix_UB_22 -0.0275689000 _diffrn_orient_matrix_UB_23 0.0434380000 _diffrn_orient_matrix_UB_31 -0.0632783000 _diffrn_orient_matrix_UB_32 -0.0448838000 _diffrn_orient_matrix_UB_33 0.0203510000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1224 _reflns_number_total 1321 _reflns_threshold_expression I>2u(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _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 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.267 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor. All Friedel pairs were merged. ; _refine_ls_abs_structure_Flack 0(10) _refine_ls_extinction_coef 0.042(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 143 _refine_ls_number_reflns 1321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0276 _refine_ls_restrained_S_all 1.059 _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^)+(0.0296P)^2^+0.24P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.0632 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _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 0.65997(15) 0.35366(12) 0.78101(11) 0.0183(3) Uani 1 1 d . . . O2 O 0.64281(14) 0.36389(11) 0.57473(10) 0.0122(2) Uani 1 1 d . . . O3 O 0.70981(16) 0.54589(11) 0.68109(10) 0.0150(3) Uani 1 1 d . . . O4 O 0.44285(14) 0.61854(11) 0.49309(11) 0.0147(3) Uani 1 1 d . . . O5 O 0.29781(14) 0.37358(11) 0.53198(10) 0.0147(3) Uani 1 1 d . . . O6 O 0.07664(15) 0.45732(12) 0.43356(12) 0.0183(3) Uani 1 1 d . . . O7 O 0.05099(16) 0.39193(13) 0.63009(12) 0.0219(3) Uani 1 1 d . . . C1 C 0.66960(19) 0.41596(16) 0.68692(15) 0.0125(3) Uani 1 1 d . . . C2 C 0.7239(2) 0.58847(16) 0.55325(14) 0.0127(3) Uani 1 1 d . . . H2 H 0.837(3) 0.6155(19) 0.5418(17) 0.015 Uiso 1 1 d . . . C3 C 0.6675(2) 0.46425(15) 0.48033(15) 0.0106(3) Uani 1 1 d . . . H3 H 0.752(3) 0.4306(18) 0.4223(18) 0.013 Uiso 1 1 d . . . C4 C 0.5916(2) 0.69306(15) 0.52415(16) 0.0146(3) Uani 1 1 d . . . H4A H 0.5710 0.7510 0.5967 0.018 Uiso 1 1 calc R . . H4B H 0.6276 0.7495 0.4539 0.018 Uiso 1 1 calc R . . C5 C 0.50199(19) 0.50842(15) 0.42045(15) 0.0117(3) Uani 1 1 d . . . H5 H 0.5276 0.5420 0.3356 0.014 Uiso 1 1 calc R . . C6 C 0.3632(2) 0.40586(16) 0.41062(14) 0.0120(3) Uani 1 1 d . . . H6 H 0.4068 0.3232 0.3698 0.014 Uiso 1 1 calc R . . C7 C 0.2072(2) 0.45742(17) 0.34103(15) 0.0150(3) Uani 1 1 d . . . H7A H 0.2264 0.5486 0.3086 0.018 Uiso 1 1 calc R . . H7B H 0.1778 0.3975 0.2716 0.018 Uiso 1 1 calc R . . C8 C 0.1352(2) 0.40644(17) 0.53885(15) 0.0154(3) 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 O1 0.0205(6) 0.0210(6) 0.0134(5) 0.0029(5) 0.0013(5) -0.0015(5) O2 0.0136(5) 0.0113(5) 0.0116(5) 0.0007(4) -0.0010(4) -0.0003(4) O3 0.0191(6) 0.0137(5) 0.0122(5) -0.0004(4) -0.0013(5) -0.0016(4) O4 0.0104(5) 0.0121(5) 0.0217(6) -0.0040(5) -0.0003(5) 0.0010(4) O5 0.0120(5) 0.0191(6) 0.0132(5) 0.0024(4) 0.0010(5) -0.0029(5) O6 0.0120(5) 0.0231(6) 0.0197(6) 0.0027(5) 0.0024(5) 0.0030(5) O7 0.0198(6) 0.0262(7) 0.0198(6) -0.0037(5) 0.0066(5) -0.0058(6) C1 0.0093(7) 0.0145(7) 0.0138(7) -0.0015(6) 0.0002(6) 0.0016(6) C2 0.0119(7) 0.0134(7) 0.0127(7) 0.0006(6) 0.0006(6) -0.0022(6) C3 0.0095(6) 0.0114(7) 0.0109(7) 0.0007(6) 0.0012(6) 0.0004(6) C4 0.0131(7) 0.0113(7) 0.0194(8) -0.0007(6) -0.0014(7) -0.0008(6) C5 0.0110(7) 0.0128(7) 0.0111(6) -0.0008(6) 0.0006(6) 0.0009(6) C6 0.0124(7) 0.0134(7) 0.0102(7) -0.0004(6) 0.0001(6) -0.0006(6) C7 0.0111(7) 0.0193(8) 0.0145(7) -0.0001(6) 0.0002(6) 0.0011(6) C8 0.0147(7) 0.0132(7) 0.0183(8) -0.0045(6) 0.0005(6) -0.0042(6) _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 1.1972(19) . ? O2 C1 1.3393(19) . ? O2 C3 1.4470(18) . ? O3 C1 1.3411(19) . ? O3 C2 1.4531(18) . ? O4 C4 1.4373(19) . ? O4 C5 1.4337(18) . ? O5 C6 1.4496(18) . ? O5 C8 1.335(2) . ? O6 C7 1.442(2) . ? O6 C8 1.333(2) . ? O7 C8 1.202(2) . ? C2 H2 0.95(2) . ? C2 C3 1.540(2) . ? C2 C4 1.516(2) . ? C3 H3 0.98(2) . ? C3 C5 1.531(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5 1.0000 . ? C5 C6 1.510(2) . ? C6 H6 1.0000 . ? C6 C7 1.539(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? 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 O2 C3 110.44(12) . . ? C1 O3 C2 110.35(12) . . ? C5 O4 C4 104.98(11) . . ? C8 O5 C6 109.99(13) . . ? C8 O6 C7 110.13(13) . . ? O1 C1 O2 124.00(14) . . ? O1 C1 O3 124.11(15) . . ? O2 C1 O3 111.89(13) . . ? O3 C2 H2 106.4(12) . . ? O3 C2 C3 103.26(12) . . ? O3 C2 C4 110.33(13) . . ? C3 C2 H2 116.1(12) . . ? C4 C2 H2 115.6(12) . . ? C4 C2 C3 104.47(13) . . ? O2 C3 C2 103.77(12) . . ? O2 C3 H3 107.9(11) . . ? O2 C3 C5 112.55(12) . . ? C2 C3 H3 114.0(11) . . ? C5 C3 C2 103.50(12) . . ? C5 C3 H3 114.6(11) . . ? O4 C4 C2 105.04(12) . . ? O4 C4 H4A 110.7 . . ? O4 C4 H4B 110.7 . . ? C2 C4 H4A 110.7 . . ? C2 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? O4 C5 C3 105.72(12) . . ? O4 C5 H5 108.2 . . ? O4 C5 C6 108.81(13) . . ? C3 C5 H5 108.2 . . ? C6 C5 C3 117.40(13) . . ? C6 C5 H5 108.2 . . ? O5 C6 C5 110.42(12) . . ? O5 C6 H6 109.9 . . ? O5 C6 C7 103.34(12) . . ? C5 C6 H6 109.9 . . ? C5 C6 C7 113.20(13) . . ? C7 C6 H6 109.9 . . ? O6 C7 C6 103.77(12) . . ? O6 C7 H7A 111.0 . . ? O6 C7 H7B 111.0 . . ? C6 C7 H7A 111.0 . . ? C6 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? O6 C8 O5 112.60(14) . . ? O7 C8 O5 123.67(16) . . ? O7 C8 O6 123.74(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C3 C5 O4 89.87(14) . . . . ? O2 C3 C5 C6 -31.68(19) . . . . ? O3 C2 C3 O2 -4.77(15) . . . . ? O3 C2 C3 C5 112.93(13) . . . . ? O3 C2 C4 O4 -84.76(15) . . . . ? O4 C5 C6 O5 -51.19(16) . . . . ? O4 C5 C6 C7 64.11(17) . . . . ? O5 C6 C7 O6 4.09(16) . . . . ? C1 O2 C3 C2 2.74(16) . . . . ? C1 O2 C3 C5 -108.48(14) . . . . ? C1 O3 C2 C3 5.46(17) . . . . ? C1 O3 C2 C4 116.63(14) . . . . ? C2 O3 C1 O1 175.40(15) . . . . ? C2 O3 C1 O2 -4.09(17) . . . . ? C2 C3 C5 O4 -21.52(15) . . . . ? C2 C3 C5 C6 -143.07(14) . . . . ? C3 O2 C1 O1 -178.83(15) . . . . ? C3 O2 C1 O3 0.66(17) . . . . ? C3 C2 C4 O4 25.62(16) . . . . ? C3 C5 C6 O5 68.74(18) . . . . ? C3 C5 C6 C7 -175.96(13) . . . . ? C4 O4 C5 C3 38.78(15) . . . . ? C4 O4 C5 C6 165.71(12) . . . . ? C4 C2 C3 O2 -120.21(12) . . . . ? C4 C2 C3 C5 -2.50(15) . . . . ? C5 O4 C4 C2 -40.34(16) . . . . ? C5 C6 C7 O6 -115.37(14) . . . . ? C6 O5 C8 O6 0.98(18) . . . . ? C6 O5 C8 O7 -178.90(15) . . . . ? C7 O6 C8 O5 1.96(19) . . . . ? C7 O6 C8 O7 -178.16(16) . . . . ? C8 O5 C6 C5 118.14(14) . . . . ? C8 O5 C6 C7 -3.21(16) . . . . ? C8 O6 C7 C6 -3.79(17) . . . . ? #===END