# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address R.Jaiswal '' M.H.Dickman '' N.Kuhnert '' _publ_contact_author_email n.kuhnert@jacobs-university.de #TrackingRef '5014_web_deposit_cif_file_0_AbhishekBanerjee_1302613529.cif' _publ_contact_author_name 'Nikolai Kuhnert' data_mtc _database_code_depnum_ccdc_archive 'CCDC 821571' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 Cl3 O4' _chemical_formula_weight 311.53 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6867(2) _cell_length_b 10.1514(4) _cell_length_c 22.3376(9) _cell_angle_alpha 85.717(2) _cell_angle_beta 83.067(2) _cell_angle_gamma 84.035(2) _cell_volume 1270.62(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3520 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 26.24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.723 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7526 _exptl_absorpt_correction_T_max 0.8589 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17407 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 5802 _reflns_number_gt 3945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. Highest peak 0.34 at 0.8230 0.6390 0.2386 [ 0.83 A from CL6 ] Deepest hole -0.41 at 0.5736 0.5765 0.2455 [ 0.78 A from CL6 ] ; _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^)+(0.0370P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0183(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5802 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.342 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.069 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 C1 C 0.8732(4) 0.5329(2) 0.07320(11) 0.0251(5) Uani 1 1 d . . . C2 C 0.7890(4) 0.6457(2) 0.03957(11) 0.0266(6) Uani 1 1 d . . . H2A H 0.656(4) 0.645(2) 0.0189(10) 0.014(6) Uiso 1 1 d . . . C3 C 0.9025(4) 0.7608(2) 0.03467(11) 0.0268(6) Uani 1 1 d . . . C4 C 1.1041(4) 0.7644(2) 0.06436(11) 0.0279(6) Uani 1 1 d . . . C5 C 1.1875(4) 0.6543(3) 0.09815(12) 0.0309(6) Uani 1 1 d . . . H5A H 1.331(4) 0.655(2) 0.1194(10) 0.024(6) Uiso 1 1 d . . . C6 C 1.0733(4) 0.5391(3) 0.10272(12) 0.0288(6) Uani 1 1 d . . . H6A H 1.138(4) 0.468(2) 0.1258(11) 0.024(6) Uiso 1 1 d . . . C7 C 0.7459(5) 0.4150(3) 0.07626(11) 0.0280(6) Uani 1 1 d . . . H7A H 0.624(4) 0.420(2) 0.0549(11) 0.027(7) Uiso 1 1 d . . . C8 C 0.7933(5) 0.2990(3) 0.10661(12) 0.0295(6) Uani 1 1 d . . . H8A H 0.917(4) 0.285(2) 0.1306(11) 0.035(7) Uiso 1 1 d . . . C9 C 0.6448(5) 0.1903(3) 0.10529(12) 0.0306(6) Uani 1 1 d . . . C10 C 0.5685(5) -0.0221(3) 0.15305(12) 0.0289(6) Uani 1 1 d . . . H10A H 0.469(4) -0.019(2) 0.1257(11) 0.021(6) Uiso 1 1 d . . . H10B H 0.671(4) -0.108(3) 0.1528(11) 0.038(8) Uiso 1 1 d . . . C11 C 0.4268(4) -0.0169(2) 0.21496(11) 0.0251(5) Uani 1 1 d . . . O1 O 0.8312(3) 0.87329(18) 0.00108(9) 0.0394(5) Uani 1 1 d . . . H1O1 H 0.727(5) 0.852(3) -0.0192(13) 0.043(9) Uiso 1 1 d . . . O2 O 1.2229(4) 0.8762(2) 0.05992(9) 0.0410(5) Uani 1 1 d . . . H1O2 H 1.161(6) 0.936(3) 0.0397(15) 0.062(11) Uiso 1 1 d . . . O3 O 0.4818(4) 0.19025(18) 0.07535(8) 0.0443(5) Uani 1 1 d . . . O4 O 0.7126(3) 0.08654(16) 0.14350(8) 0.0307(4) Uani 1 1 d . . . Cl1 Cl 0.24281(12) 0.13375(7) 0.22261(3) 0.03939(19) Uani 1 1 d . . . Cl2 Cl 0.62157(11) -0.03184(7) 0.27238(3) 0.03347(18) Uani 1 1 d . . . Cl3 Cl 0.24822(11) -0.15133(6) 0.22504(3) 0.03755(19) Uani 1 1 d . . . C12 C -0.0823(4) 1.0593(2) 0.42592(11) 0.0239(5) Uani 1 1 d . . . C13 C -0.1842(4) 1.1596(2) 0.46301(11) 0.0260(6) Uani 1 1 d . . . H13A H -0.321(4) 1.1557(19) 0.4849(9) 0.005(5) Uiso 1 1 d . . . C14 C -0.0652(4) 1.2677(2) 0.47045(11) 0.0256(5) Uani 1 1 d . . . C15 C 0.1594(4) 1.2795(2) 0.43919(11) 0.0261(6) Uani 1 1 d . . . C16 C 0.2609(5) 1.1827(3) 0.40142(12) 0.0319(6) Uani 1 1 d . . . H16A H 0.407(5) 1.193(3) 0.3812(12) 0.042(8) Uiso 1 1 d . . . C17 C 0.1425(4) 1.0732(3) 0.39470(12) 0.0293(6) Uani 1 1 d . . . H17A H 0.220(4) 1.006(2) 0.3684(12) 0.034(7) Uiso 1 1 d . . . C18 C -0.2112(5) 0.9439(3) 0.42100(11) 0.0265(6) Uani 1 1 d . . . H18A H -0.365(5) 0.948(3) 0.4385(12) 0.047(8) Uiso 1 1 d . . . C19 C -0.1274(5) 0.8340(3) 0.39361(12) 0.0278(6) Uani 1 1 d . . . H19A H 0.027(4) 0.823(2) 0.3743(11) 0.028(7) Uiso 1 1 d . . . C20 C -0.2734(4) 0.7246(2) 0.39206(11) 0.0267(6) Uani 1 1 d . . . C21 C -0.2588(5) 0.5095(3) 0.35316(13) 0.0332(6) Uani 1 1 d . . . H21B H -0.202(5) 0.438(3) 0.3809(14) 0.058(10) Uiso 1 1 d . . . H21A H -0.432(5) 0.529(2) 0.3577(11) 0.039(8) Uiso 1 1 d . . . C22 C -0.1799(4) 0.4756(2) 0.28840(11) 0.0258(6) Uani 1 1 d . . . O5 O -0.1554(4) 1.36831(19) 0.50723(9) 0.0363(5) Uani 1 1 d . . . H1O5 H -0.266(6) 1.347(3) 0.5245(15) 0.057(11) Uiso 1 1 d . . . O6 O 0.2845(3) 1.3847(2) 0.44518(10) 0.0392(5) Uani 1 1 d . . . H1O6 H 0.213(5) 1.432(3) 0.4670(12) 0.032(9) Uiso 1 1 d . . . O7 O -0.4783(3) 0.72001(18) 0.41257(9) 0.0443(5) Uani 1 1 d . . . O8 O -0.1460(3) 0.62423(18) 0.36271(9) 0.0407(5) Uani 1 1 d . . . Cl4 Cl -0.28901(12) 0.32275(7) 0.27755(3) 0.03930(19) Uani 1 1 d . . . Cl5 Cl 0.13349(11) 0.45896(7) 0.27324(3) 0.0423(2) Uani 1 1 d . . . Cl6 Cl -0.29866(13) 0.60002(8) 0.23792(4) 0.0498(2) 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 C1 0.0282(13) 0.0283(14) 0.0188(13) 0.0005(11) -0.0023(10) -0.0053(11) C2 0.0267(13) 0.0288(14) 0.0264(14) -0.0032(11) -0.0066(11) -0.0068(11) C3 0.0284(13) 0.0266(14) 0.0258(14) 0.0005(11) -0.0053(10) -0.0039(11) C4 0.0278(13) 0.0300(14) 0.0274(15) -0.0018(12) -0.0040(11) -0.0096(11) C5 0.0266(14) 0.0375(16) 0.0304(15) -0.0013(12) -0.0091(11) -0.0048(12) C6 0.0316(14) 0.0274(15) 0.0276(15) 0.0019(12) -0.0055(11) -0.0035(12) C7 0.0310(14) 0.0326(15) 0.0217(14) -0.0011(12) -0.0058(11) -0.0067(12) C8 0.0336(15) 0.0329(15) 0.0242(14) 0.0017(12) -0.0077(11) -0.0112(12) C9 0.0370(15) 0.0295(15) 0.0263(15) 0.0022(12) -0.0077(12) -0.0064(12) C10 0.0344(15) 0.0230(14) 0.0303(16) 0.0004(12) -0.0068(12) -0.0049(12) C11 0.0231(12) 0.0211(13) 0.0316(15) -0.0038(11) -0.0048(10) -0.0001(10) O1 0.0451(12) 0.0302(11) 0.0489(13) 0.0091(9) -0.0268(10) -0.0160(9) O2 0.0458(12) 0.0324(11) 0.0503(13) 0.0078(10) -0.0237(10) -0.0164(10) O3 0.0596(13) 0.0398(12) 0.0409(12) 0.0108(10) -0.0285(10) -0.0224(10) O4 0.0332(10) 0.0277(10) 0.0323(10) 0.0068(8) -0.0081(8) -0.0095(8) Cl1 0.0365(4) 0.0298(4) 0.0502(5) -0.0061(3) -0.0089(3) 0.0115(3) Cl2 0.0308(3) 0.0407(4) 0.0292(4) 0.0010(3) -0.0095(3) -0.0001(3) Cl3 0.0307(4) 0.0324(4) 0.0497(5) 0.0019(3) -0.0026(3) -0.0095(3) C12 0.0258(13) 0.0241(13) 0.0221(13) -0.0030(11) -0.0025(10) -0.0022(10) C13 0.0236(13) 0.0259(14) 0.0264(14) -0.0006(11) 0.0070(11) -0.0041(11) C14 0.0295(13) 0.0238(13) 0.0220(14) -0.0024(11) 0.0028(10) -0.0023(11) C15 0.0252(13) 0.0239(14) 0.0295(15) -0.0002(11) -0.0012(10) -0.0068(11) C16 0.0235(14) 0.0345(16) 0.0366(16) -0.0070(13) 0.0052(11) -0.0052(12) C17 0.0278(14) 0.0307(15) 0.0279(15) -0.0077(12) 0.0059(11) -0.0019(12) C18 0.0268(14) 0.0284(15) 0.0235(14) -0.0008(11) 0.0014(11) -0.0046(11) C19 0.0269(14) 0.0322(15) 0.0248(14) -0.0056(12) -0.0012(11) -0.0043(12) C20 0.0321(14) 0.0257(14) 0.0216(14) -0.0035(11) 0.0004(11) -0.0016(11) C21 0.0380(17) 0.0298(16) 0.0330(17) -0.0102(13) 0.0000(13) -0.0084(13) C22 0.0183(12) 0.0228(13) 0.0363(15) -0.0056(11) -0.0018(10) -0.0012(10) O5 0.0358(12) 0.0304(11) 0.0413(12) -0.0123(9) 0.0146(9) -0.0122(9) O6 0.0318(11) 0.0326(12) 0.0533(14) -0.0174(11) 0.0110(9) -0.0113(9) O7 0.0437(12) 0.0351(11) 0.0521(13) -0.0158(10) 0.0222(9) -0.0170(9) O8 0.0331(10) 0.0343(11) 0.0575(13) -0.0257(10) 0.0023(9) -0.0081(9) Cl4 0.0331(4) 0.0305(4) 0.0564(5) -0.0191(3) 0.0004(3) -0.0079(3) Cl5 0.0196(3) 0.0450(4) 0.0635(5) -0.0216(4) 0.0000(3) -0.0006(3) Cl6 0.0492(5) 0.0457(5) 0.0528(5) 0.0114(4) -0.0128(4) 0.0019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.391(3) . ? C1 C2 1.397(3) . ? C1 C7 1.456(3) . ? C2 C3 1.383(3) . ? C2 H2A 0.93(2) . ? C3 O1 1.371(3) . ? C3 C4 1.397(3) . ? C4 O2 1.372(3) . ? C4 C5 1.376(3) . ? C5 C6 1.388(3) . ? C5 H5A 0.99(2) . ? C6 H6A 0.93(2) . ? C7 C8 1.333(3) . ? C7 H7A 0.88(2) . ? C8 C9 1.462(3) . ? C8 H8A 0.93(2) . ? C9 O3 1.207(3) . ? C9 O4 1.359(3) . ? C10 O4 1.430(3) . ? C10 C11 1.516(4) . ? C10 H10A 0.88(2) . ? C10 H10B 1.00(3) . ? C11 Cl1 1.768(2) . ? C11 Cl3 1.770(2) . ? C11 Cl2 1.782(2) . ? O1 H1O1 0.84(3) . ? O2 H1O2 0.81(3) . ? C12 C13 1.395(3) . ? C12 C17 1.396(3) . ? C12 C18 1.463(3) . ? C13 C14 1.378(3) . ? C13 H13A 0.87(2) . ? C14 O5 1.377(3) . ? C14 C15 1.392(3) . ? C15 O6 1.366(3) . ? C15 C16 1.378(3) . ? C16 C17 1.385(4) . ? C16 H16A 0.91(3) . ? C17 H17A 0.97(3) . ? C18 C19 1.329(4) . ? C18 H18A 0.91(3) . ? C19 C20 1.459(3) . ? C19 H19A 0.93(2) . ? C20 O7 1.204(3) . ? C20 O8 1.351(3) . ? C21 O8 1.428(3) . ? C21 C22 1.516(4) . ? C21 H21B 0.97(3) . ? C21 H21A 0.98(3) . ? C22 Cl6 1.765(2) . ? C22 Cl5 1.766(2) . ? C22 Cl4 1.773(2) . ? O5 H1O5 0.74(3) . ? O6 H1O6 0.76(3) . ? 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 C6 C1 C2 118.4(2) . . ? C6 C1 C7 123.1(2) . . ? C2 C1 C7 118.4(2) . . ? C3 C2 C1 121.3(2) . . ? C3 C2 H2A 118.2(13) . . ? C1 C2 H2A 120.5(13) . . ? O1 C3 C2 123.7(2) . . ? O1 C3 C4 117.0(2) . . ? C2 C3 C4 119.3(2) . . ? O2 C4 C5 119.1(2) . . ? O2 C4 C3 120.9(2) . . ? C5 C4 C3 120.0(2) . . ? C4 C5 C6 120.4(2) . . ? C4 C5 H5A 121.0(13) . . ? C6 C5 H5A 118.6(13) . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6A 116.6(14) . . ? C1 C6 H6A 122.8(14) . . ? C8 C7 C1 127.9(2) . . ? C8 C7 H7A 115.7(16) . . ? C1 C7 H7A 116.4(16) . . ? C7 C8 C9 120.9(2) . . ? C7 C8 H8A 121.7(16) . . ? C9 C8 H8A 117.4(16) . . ? O3 C9 O4 123.3(2) . . ? O3 C9 C8 126.0(2) . . ? O4 C9 C8 110.7(2) . . ? O4 C10 C11 109.2(2) . . ? O4 C10 H10A 111.4(15) . . ? C11 C10 H10A 108.7(16) . . ? O4 C10 H10B 110.1(14) . . ? C11 C10 H10B 106.9(15) . . ? H10A C10 H10B 110(2) . . ? C10 C11 Cl1 111.77(18) . . ? C10 C11 Cl3 108.12(17) . . ? Cl1 C11 Cl3 109.42(12) . . ? C10 C11 Cl2 110.41(17) . . ? Cl1 C11 Cl2 108.02(13) . . ? Cl3 C11 Cl2 109.07(13) . . ? C3 O1 H1O1 105.9(19) . . ? C4 O2 H1O2 112(2) . . ? C9 O4 C10 117.98(19) . . ? C13 C12 C17 118.1(2) . . ? C13 C12 C18 119.8(2) . . ? C17 C12 C18 122.2(2) . . ? C14 C13 C12 121.5(2) . . ? C14 C13 H13A 115.5(13) . . ? C12 C13 H13A 122.8(13) . . ? C13 C14 O5 124.0(2) . . ? C13 C14 C15 119.6(2) . . ? O5 C14 C15 116.4(2) . . ? O6 C15 C16 118.6(2) . . ? O6 C15 C14 121.8(2) . . ? C16 C15 C14 119.7(2) . . ? C15 C16 C17 120.6(2) . . ? C15 C16 H16A 117.9(17) . . ? C17 C16 H16A 121.5(17) . . ? C16 C17 C12 120.5(3) . . ? C16 C17 H17A 118.4(15) . . ? C12 C17 H17A 121.1(15) . . ? C19 C18 C12 126.7(2) . . ? C19 C18 H18A 116.9(18) . . ? C12 C18 H18A 116.4(18) . . ? C18 C19 C20 121.7(2) . . ? C18 C19 H19A 121.6(15) . . ? C20 C19 H19A 116.7(15) . . ? O7 C20 O8 122.6(2) . . ? O7 C20 C19 127.3(2) . . ? O8 C20 C19 110.1(2) . . ? O8 C21 C22 106.7(2) . . ? O8 C21 H21B 107.3(17) . . ? C22 C21 H21B 110.1(18) . . ? O8 C21 H21A 110.4(15) . . ? C22 C21 H21A 108.1(15) . . ? H21B C21 H21A 114(2) . . ? C21 C22 Cl6 110.27(19) . . ? C21 C22 Cl5 111.31(18) . . ? Cl6 C22 Cl5 109.14(13) . . ? C21 C22 Cl4 107.87(17) . . ? Cl6 C22 Cl4 109.18(13) . . ? Cl5 C22 Cl4 109.04(13) . . ? C14 O5 H1O5 107(3) . . ? C15 O6 H1O6 110(2) . . ? C20 O8 C21 119.4(2) . . ? 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 C6 C1 C2 C3 1.0(4) . . . . ? C7 C1 C2 C3 -179.7(2) . . . . ? C1 C2 C3 O1 178.3(2) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? O1 C3 C4 O2 0.3(4) . . . . ? C2 C3 C4 O2 179.2(2) . . . . ? O1 C3 C4 C5 -179.1(2) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? O2 C4 C5 C6 -179.0(2) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? C2 C1 C6 C5 -0.8(4) . . . . ? C7 C1 C6 C5 180.0(2) . . . . ? C6 C1 C7 C8 0.8(4) . . . . ? C2 C1 C7 C8 -178.5(3) . . . . ? C1 C7 C8 C9 179.4(2) . . . . ? C7 C8 C9 O3 4.8(5) . . . . ? C7 C8 C9 O4 -174.5(2) . . . . ? O4 C10 C11 Cl1 58.9(2) . . . . ? O4 C10 C11 Cl3 179.38(16) . . . . ? O4 C10 C11 Cl2 -61.4(2) . . . . ? O3 C9 O4 C10 -6.5(4) . . . . ? C8 C9 O4 C10 172.9(2) . . . . ? C11 C10 O4 C9 -105.6(2) . . . . ? C17 C12 C13 C14 -2.0(4) . . . . ? C18 C12 C13 C14 177.8(2) . . . . ? C12 C13 C14 O5 -178.9(2) . . . . ? C12 C13 C14 C15 1.7(4) . . . . ? C13 C14 C15 O6 -179.9(2) . . . . ? O5 C14 C15 O6 0.7(4) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? O5 C14 C15 C16 -179.9(2) . . . . ? O6 C15 C16 C17 178.9(2) . . . . ? C14 C15 C16 C17 -0.6(4) . . . . ? C15 C16 C17 C12 0.2(4) . . . . ? C13 C12 C17 C16 1.0(4) . . . . ? C18 C12 C17 C16 -178.8(2) . . . . ? C13 C12 C18 C19 -171.4(3) . . . . ? C17 C12 C18 C19 8.3(4) . . . . ? C12 C18 C19 C20 179.6(2) . . . . ? C18 C19 C20 O7 2.0(4) . . . . ? C18 C19 C20 O8 -178.8(2) . . . . ? O8 C21 C22 Cl6 -67.5(2) . . . . ? O8 C21 C22 Cl5 53.8(3) . . . . ? O8 C21 C22 Cl4 173.40(18) . . . . ? O7 C20 O8 C21 2.5(4) . . . . ? C19 C20 O8 C21 -176.7(2) . . . . ? C22 C21 O8 C20 135.9(2) . . . . ? loop_ _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 O1 H1O1 O3 0.84(3) 1.93(3) 2.763(2) 172(3) 2_665 O2 H1O2 O1 0.81(3) 2.08(3) 2.800(3) 148(3) 2_775 O2 H1O2 O1 0.81(3) 2.32(3) 2.724(3) 112(3) . O5 H1O5 O7 0.74(3) 2.03(3) 2.757(3) 167(3) 2_476 O6 H1O6 O5 0.76(3) 2.13(3) 2.790(3) 145(3) 2_586 O6 H1O6 O5 0.76(3) 2.31(3) 2.724(3) 115(2) . # Attachment '5015_web_deposit_cif_file_1_AbhishekBanerjee_1302613529.cif' data_s3 _database_code_depnum_ccdc_archive 'CCDC 821572' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 O8' _chemical_formula_weight 320.33 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0784(8) _cell_length_b 9.5830(7) _cell_length_c 9.3296(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.683(4) _cell_angle_gamma 90.00 _cell_volume 785.15(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9912 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 26.96 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.80 _exptl_crystal_size_min 0.60 _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9164 _exptl_absorpt_correction_T_max 0.9364 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27061 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.10 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 3291 _reflns_number_gt 2831 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0575P)^2^+0.2130P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.088(7) _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 0.2(10) _refine_ls_number_reflns 3291 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.444 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.059 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 C1 C 0.0422(2) 0.7008(2) 0.7127(2) 0.0212(4) Uani 1 1 d . . . C2 C -0.0395(2) 0.59285(19) 0.7870(2) 0.0209(4) Uani 1 1 d . . . H2A H -0.0068 0.6053 0.8958 0.025 Uiso 1 1 calc R . . H2B H -0.1507 0.6095 0.7551 0.025 Uiso 1 1 calc R . . C3 C -0.0065(2) 0.4443(2) 0.7489(2) 0.0195(4) Uani 1 1 d . . . H3A H -0.0514 0.3799 0.8109 0.023 Uiso 1 1 calc R . . C4 C 0.1650(2) 0.42402(19) 0.79179(19) 0.0182(4) Uani 1 1 d . . . H4A H 0.2041 0.4437 0.9000 0.022 Uiso 1 1 calc R . . C5 C 0.2424(2) 0.5220(2) 0.7064(2) 0.0201(4) Uani 1 1 d . . . H5A H 0.2018 0.5065 0.5975 0.024 Uiso 1 1 calc R . . C6 C 0.2147(2) 0.6722(2) 0.7449(2) 0.0235(4) Uani 1 1 d . . . H6A H 0.2612 0.7363 0.6857 0.028 Uiso 1 1 calc R . . H6B H 0.2630 0.6893 0.8511 0.028 Uiso 1 1 calc R . . C7 C 0.4435(2) 0.3562(2) 0.7256(2) 0.0277(5) Uani 1 1 d . . . C8 C 0.3577(2) 0.2545(2) 0.8060(2) 0.0266(5) Uani 1 1 d . . . C9 C 0.0178(2) 0.8431(2) 0.7790(2) 0.0236(4) Uani 1 1 d . . . C10 C -0.0920(3) 1.0654(2) 0.7398(3) 0.0353(5) Uani 1 1 d . . . H10A H -0.1495 1.1242 0.6589 0.053 Uiso 1 1 calc R . . H10B H 0.0036 1.1119 0.7888 0.053 Uiso 1 1 calc R . . H10C H -0.1525 1.0499 0.8117 0.053 Uiso 1 1 calc R . . C11 C 0.6146(2) 0.3474(3) 0.7853(3) 0.0407(6) Uani 1 1 d . . . H11A H 0.6636 0.4135 0.7319 0.061 Uiso 1 1 calc R . . H11B H 0.6488 0.2525 0.7716 0.061 Uiso 1 1 calc R . . H11C H 0.6421 0.3705 0.8911 0.061 Uiso 1 1 calc R . . C12 C 0.4569(3) 0.3993(4) 0.4765(3) 0.0574(8) Uani 1 1 d . . . H12A H 0.4152 0.3660 0.3750 0.086 Uiso 1 1 calc R . . H12B H 0.5679 0.3887 0.5034 0.086 Uiso 1 1 calc R . . H12C H 0.4308 0.4979 0.4830 0.086 Uiso 1 1 calc R . . C13 C 0.3724(3) 0.1024(3) 0.7644(4) 0.0481(7) Uani 1 1 d . . . H13A H 0.3158 0.0432 0.8175 0.072 Uiso 1 1 calc R . . H13B H 0.4800 0.0754 0.7915 0.072 Uiso 1 1 calc R . . H13C H 0.3309 0.0907 0.6574 0.072 Uiso 1 1 calc R . . C14 C 0.3442(3) 0.2150(4) 1.0562(3) 0.0562(8) Uani 1 1 d . . . H14A H 0.3955 0.2396 1.1586 0.084 Uiso 1 1 calc R . . H14B H 0.3475 0.1136 1.0437 0.084 Uiso 1 1 calc R . . H14C H 0.2379 0.2460 1.0340 0.084 Uiso 1 1 calc R . . O1 O 0.40370(14) 0.49696(14) 0.74865(16) 0.0257(3) Uani 1 1 d . . . O2 O 0.19905(14) 0.28316(14) 0.76481(15) 0.0232(3) Uani 1 1 d . . . O3 O -0.02799(16) 0.69067(15) 0.55883(14) 0.0257(3) Uani 1 1 d . . . H3 H -0.0048 0.7608 0.5151 0.039 Uiso 1 1 calc R . . O4 O 0.0628(2) 0.86821(18) 0.90873(17) 0.0471(5) Uani 1 1 d . . . O5 O -0.05906(17) 0.93261(15) 0.68069(15) 0.0309(4) Uani 1 1 d . . . O6 O -0.07306(14) 0.41186(14) 0.59602(14) 0.0241(3) Uani 1 1 d . . . H6 H -0.0127 0.3619 0.5635 0.036 Uiso 1 1 calc R . . O7 O 0.39411(18) 0.31974(18) 0.57562(17) 0.0389(4) Uani 1 1 d . . . O8 O 0.41928(17) 0.28169(18) 0.95759(17) 0.0371(4) 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 C1 0.0250(10) 0.0186(10) 0.0195(9) -0.0012(8) 0.0046(7) 0.0020(8) C2 0.0198(10) 0.0216(11) 0.0219(9) 0.0016(8) 0.0069(8) 0.0040(8) C3 0.0183(9) 0.0197(10) 0.0215(9) 0.0019(7) 0.0071(7) 0.0003(7) C4 0.0194(9) 0.0154(9) 0.0194(8) 0.0017(7) 0.0040(7) 0.0032(7) C5 0.0165(9) 0.0194(10) 0.0242(10) -0.0008(7) 0.0047(7) -0.0011(7) C6 0.0226(10) 0.0192(11) 0.0289(10) 0.0009(8) 0.0070(8) -0.0004(8) C7 0.0209(10) 0.0256(11) 0.0379(11) -0.0048(9) 0.0100(8) 0.0011(8) C8 0.0193(10) 0.0229(11) 0.0378(11) 0.0004(8) 0.0076(8) 0.0061(8) C9 0.0264(10) 0.0179(10) 0.0264(10) -0.0027(8) 0.0069(8) 0.0007(8) C10 0.0454(14) 0.0203(11) 0.0409(13) -0.0027(9) 0.0121(10) 0.0088(9) C11 0.0192(11) 0.0368(14) 0.0668(16) -0.0031(11) 0.0119(10) 0.0034(9) C12 0.0571(17) 0.077(2) 0.0481(16) 0.0047(14) 0.0326(13) 0.0093(15) C13 0.0352(13) 0.0237(13) 0.090(2) -0.0023(13) 0.0243(13) 0.0061(10) C14 0.0586(17) 0.067(2) 0.0450(15) 0.0298(14) 0.0170(13) 0.0174(15) O1 0.0162(7) 0.0208(7) 0.0403(8) -0.0035(6) 0.0075(6) -0.0006(5) O2 0.0206(7) 0.0164(7) 0.0337(8) 0.0004(6) 0.0087(6) 0.0011(5) O3 0.0373(8) 0.0199(7) 0.0185(7) 0.0017(5) 0.0046(6) 0.0012(6) O4 0.0697(12) 0.0345(10) 0.0288(9) -0.0115(7) -0.0027(8) 0.0165(8) O5 0.0447(9) 0.0189(8) 0.0281(7) -0.0012(6) 0.0073(6) 0.0095(6) O6 0.0211(7) 0.0256(8) 0.0243(7) -0.0049(6) 0.0033(5) 0.0004(6) O7 0.0395(9) 0.0453(10) 0.0367(8) -0.0091(7) 0.0182(7) -0.0009(8) O8 0.0274(8) 0.0464(10) 0.0351(8) 0.0087(7) 0.0037(6) 0.0079(7) _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 C1 O3 1.418(2) . ? C1 C9 1.537(3) . ? C1 C2 1.537(3) . ? C1 C6 1.542(3) . ? C2 C3 1.516(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O6 1.435(2) . ? C3 C4 1.518(2) . ? C3 H3A 1.0000 . ? C4 O2 1.421(2) . ? C4 C5 1.515(3) . ? C4 H4A 1.0000 . ? C5 O1 1.437(2) . ? C5 C6 1.519(3) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O7 1.401(3) . ? C7 O1 1.427(3) . ? C7 C11 1.514(3) . ? C7 C8 1.554(3) . ? C8 O8 1.407(3) . ? C8 O2 1.420(2) . ? C8 C13 1.523(3) . ? C9 O4 1.199(3) . ? C9 O5 1.319(2) . ? C10 O5 1.448(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O7 1.424(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O8 1.428(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O3 H3 0.8400 . ? O6 H6 0.8400 . ? 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 O3 C1 C9 113.26(15) . . ? O3 C1 C2 105.43(15) . . ? C9 C1 C2 106.26(14) . . ? O3 C1 C6 111.04(16) . . ? C9 C1 C6 108.79(16) . . ? C2 C1 C6 111.98(15) . . ? C3 C2 C1 112.31(15) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? O6 C3 C2 112.20(15) . . ? O6 C3 C4 112.30(14) . . ? C2 C3 C4 108.00(16) . . ? O6 C3 H3A 108.1 . . ? C2 C3 H3A 108.1 . . ? C4 C3 H3A 108.1 . . ? O2 C4 C5 110.16(14) . . ? O2 C4 C3 109.24(15) . . ? C5 C4 C3 111.33(14) . . ? O2 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? O1 C5 C4 109.18(15) . . ? O1 C5 C6 108.18(15) . . ? C4 C5 C6 109.61(15) . . ? O1 C5 H5A 109.9 . . ? C4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? C5 C6 C1 110.08(16) . . ? C5 C6 H6A 109.6 . . ? C1 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C1 C6 H6B 109.6 . . ? H6A C6 H6B 108.2 . . ? O7 C7 O1 110.90(17) . . ? O7 C7 C11 113.08(18) . . ? O1 C7 C11 105.81(17) . . ? O7 C7 C8 104.68(16) . . ? O1 C7 C8 110.08(16) . . ? C11 C7 C8 112.38(18) . . ? O8 C8 O2 110.73(16) . . ? O8 C8 C13 113.30(19) . . ? O2 C8 C13 105.35(18) . . ? O8 C8 C7 104.40(17) . . ? O2 C8 C7 110.22(16) . . ? C13 C8 C7 112.94(19) . . ? O4 C9 O5 123.78(18) . . ? O4 C9 C1 122.52(18) . . ? O5 C9 C1 113.68(16) . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O7 C12 H12A 109.5 . . ? O7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O8 C14 H14A 109.5 . . ? O8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 O1 C5 113.32(14) . . ? C8 O2 C4 112.78(14) . . ? C1 O3 H3 109.5 . . ? C9 O5 C10 115.50(16) . . ? C3 O6 H6 109.5 . . ? C7 O7 C12 115.8(2) . . ? C8 O8 C14 115.6(2) . . ? 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 O3 C1 C2 C3 67.75(18) . . . . ? C9 C1 C2 C3 -171.78(16) . . . . ? C6 C1 C2 C3 -53.1(2) . . . . ? C1 C2 C3 O6 -68.31(19) . . . . ? C1 C2 C3 C4 55.98(19) . . . . ? O6 C3 C4 O2 -58.93(19) . . . . ? C2 C3 C4 O2 176.84(14) . . . . ? O6 C3 C4 C5 63.0(2) . . . . ? C2 C3 C4 C5 -61.28(19) . . . . ? O2 C4 C5 O1 -57.54(18) . . . . ? C3 C4 C5 O1 -178.88(15) . . . . ? O2 C4 C5 C6 -175.87(16) . . . . ? C3 C4 C5 C6 62.78(19) . . . . ? O1 C5 C6 C1 -175.66(16) . . . . ? C4 C5 C6 C1 -56.7(2) . . . . ? O3 C1 C6 C5 -65.1(2) . . . . ? C9 C1 C6 C5 169.58(15) . . . . ? C2 C1 C6 C5 52.4(2) . . . . ? O7 C7 C8 O8 174.11(15) . . . . ? O1 C7 C8 O8 -66.6(2) . . . . ? C11 C7 C8 O8 51.0(2) . . . . ? O7 C7 C8 O2 -66.9(2) . . . . ? O1 C7 C8 O2 52.3(2) . . . . ? C11 C7 C8 O2 169.96(18) . . . . ? O7 C7 C8 C13 50.6(2) . . . . ? O1 C7 C8 C13 169.84(19) . . . . ? C11 C7 C8 C13 -72.5(2) . . . . ? O3 C1 C9 O4 176.4(2) . . . . ? C2 C1 C9 O4 61.1(3) . . . . ? C6 C1 C9 O4 -59.6(3) . . . . ? O3 C1 C9 O5 -2.4(2) . . . . ? C2 C1 C9 O5 -117.67(17) . . . . ? C6 C1 C9 O5 121.60(19) . . . . ? O7 C7 O1 C5 60.7(2) . . . . ? C11 C7 O1 C5 -176.29(17) . . . . ? C8 C7 O1 C5 -54.6(2) . . . . ? C4 C5 O1 C7 57.3(2) . . . . ? C6 C5 O1 C7 176.55(16) . . . . ? O8 C8 O2 C4 59.2(2) . . . . ? C13 C8 O2 C4 -177.99(18) . . . . ? C7 C8 O2 C4 -55.9(2) . . . . ? C5 C4 O2 C8 59.06(18) . . . . ? C3 C4 O2 C8 -178.35(15) . . . . ? O4 C9 O5 C10 -2.1(3) . . . . ? C1 C9 O5 C10 176.68(17) . . . . ? O1 C7 O7 C12 61.1(2) . . . . ? C11 C7 O7 C12 -57.5(3) . . . . ? C8 C7 O7 C12 179.8(2) . . . . ? O2 C8 O8 C14 52.9(2) . . . . ? C13 C8 O8 C14 -65.2(2) . . . . ? C7 C8 O8 C14 171.52(19) . . . . ? loop_ _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 O3 H3 O6 0.84 2.01 2.8449(19) 172.1 2_556 O6 H6 O3 0.84 2.08 2.8449(19) 150.3 2_546 O6 H6 O2 0.84 2.44 2.8515(18) 110.9 . O6 H6 O5 0.84 2.61 3.116(2) 119.8 2_546 # Attachment '5016_web_deposit_cif_file_2_AbhishekBanerjee_1302613529.cif' data_s4 _database_code_depnum_ccdc_archive 'CCDC 821573' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 O8' _chemical_formula_weight 320.33 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 10.0094(11) _cell_length_b 12.1210(10) _cell_length_c 12.9524(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1571.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8566 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 26.07 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.57 _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8085 _exptl_absorpt_correction_T_max 0.9394 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28020 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 27.10 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 3445 _reflns_number_gt 2807 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. Highest peak 0.18 at 0.0153 0.1995 0.9343 [ 1.18 A from H11B ] Deepest hole -0.21 at 0.1780 0.8235 0.4065 [ 0.77 A from C7 ] ; _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^)+(0.0557P)^2^+0.0800P] 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 none _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 -0.4(9) _refine_ls_number_reflns 3445 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.183 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.056 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 C1 C 0.04901(18) 0.19077(15) 0.59309(12) 0.0233(4) Uani 1 1 d . . . C2 C 0.18435(18) 0.16856(15) 0.64429(12) 0.0236(4) Uani 1 1 d . . . H2A H 0.2004 0.0881 0.6477 0.028 Uiso 1 1 calc R . . H2B H 0.2565 0.2022 0.6025 0.028 Uiso 1 1 calc R . . C3 C 0.18626(17) 0.21689(13) 0.75250(13) 0.0201(4) Uani 1 1 d . . . H3A H 0.1141 0.1821 0.7949 0.024 Uiso 1 1 calc R . . C4 C 0.16398(17) 0.34004(14) 0.74722(13) 0.0190(4) Uani 1 1 d . . . H4A H 0.2312 0.3741 0.6999 0.023 Uiso 1 1 calc R . . C5 C 0.02432(19) 0.36230(14) 0.70702(13) 0.0231(4) Uani 1 1 d . . . H5A H -0.0427 0.3267 0.7536 0.028 Uiso 1 1 calc R . . C6 C 0.01239(19) 0.31361(14) 0.59871(13) 0.0238(4) Uani 1 1 d . . . H6A H 0.0716 0.3553 0.5515 0.029 Uiso 1 1 calc R . . H6B H -0.0806 0.3232 0.5742 0.029 Uiso 1 1 calc R . . C7 C 0.32793(17) 0.23880(15) 0.89840(13) 0.0209(4) Uani 1 1 d . . . C8 C 0.30275(18) 0.36512(14) 0.89513(13) 0.0207(4) Uani 1 1 d . . . C9 C 0.04880(19) 0.15567(15) 0.47961(13) 0.0248(4) Uani 1 1 d . . . C10 C 0.1461(2) 0.1790(2) 0.31551(14) 0.0405(5) Uani 1 1 d . . . H10A H 0.2210 0.2173 0.2825 0.061 Uiso 1 1 calc R . . H10B H 0.0619 0.2043 0.2850 0.061 Uiso 1 1 calc R . . H10C H 0.1553 0.0993 0.3049 0.061 Uiso 1 1 calc R . . C11 C 0.46663(19) 0.20801(16) 0.93310(13) 0.0281(4) Uani 1 1 d . . . H11A H 0.4760 0.1275 0.9327 0.042 Uiso 1 1 calc R . . H11B H 0.4818 0.2359 1.0031 0.042 Uiso 1 1 calc R . . H11C H 0.5324 0.2405 0.8860 0.042 Uiso 1 1 calc R . . C12 C 0.2289(2) 0.08373(17) 0.98661(17) 0.0383(5) Uani 1 1 d . . . H12A H 0.1551 0.0657 1.0334 0.057 Uiso 1 1 calc R . . H12B H 0.3139 0.0642 1.0194 0.057 Uiso 1 1 calc R . . H12C H 0.2189 0.0421 0.9222 0.057 Uiso 1 1 calc R . . C13 C 0.29813(19) 0.41750(16) 1.00154(13) 0.0263(4) Uani 1 1 d . . . H13A H 0.2817 0.4969 0.9947 0.039 Uiso 1 1 calc R . . H13B H 0.3836 0.4056 1.0367 0.039 Uiso 1 1 calc R . . H13C H 0.2261 0.3838 1.0420 0.039 Uiso 1 1 calc R . . C14 C 0.4039(2) 0.52288(16) 0.81242(16) 0.0387(5) Uani 1 1 d . . . H14A H 0.4805 0.5428 0.7691 0.058 Uiso 1 1 calc R . . H14B H 0.4080 0.5641 0.8774 0.058 Uiso 1 1 calc R . . H14C H 0.3209 0.5410 0.7761 0.058 Uiso 1 1 calc R . . O1 O 0.31392(12) 0.19271(10) 0.79739(8) 0.0211(3) Uani 1 1 d . . . O2 O 0.17614(11) 0.38779(9) 0.84863(8) 0.0205(3) Uani 1 1 d . . . O3 O -0.05124(14) 0.12768(11) 0.64431(9) 0.0307(3) Uani 1 1 d . . . H3 H -0.0905 0.0872 0.6013 0.046 Uiso 1 1 calc R . . O4 O -0.03359(16) 0.09428(13) 0.44441(10) 0.0426(4) Uani 1 1 d . . . O5 O 0.14616(14) 0.20279(11) 0.42559(9) 0.0319(3) Uani 1 1 d . . . O6 O -0.00549(15) 0.47564(11) 0.69692(10) 0.0365(4) Uani 1 1 d . . . H6 H 0.0275 0.5104 0.7469 0.055 Uiso 1 1 calc R . . O7 O 0.22722(12) 0.19856(10) 0.96469(9) 0.0243(3) Uani 1 1 d . . . O8 O 0.40742(12) 0.40754(11) 0.83367(9) 0.0258(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 C1 0.0277(10) 0.0215(10) 0.0207(8) 0.0005(7) -0.0027(7) -0.0039(8) C2 0.0289(10) 0.0185(9) 0.0234(9) -0.0043(7) -0.0036(7) 0.0025(8) C3 0.0195(9) 0.0187(9) 0.0221(8) -0.0008(7) -0.0037(7) 0.0018(7) C4 0.0207(9) 0.0181(9) 0.0182(8) -0.0027(7) -0.0017(7) 0.0004(7) C5 0.0256(10) 0.0198(10) 0.0240(8) -0.0019(7) -0.0016(7) 0.0037(8) C6 0.0268(10) 0.0233(10) 0.0213(8) 0.0006(7) -0.0052(7) 0.0011(8) C7 0.0214(10) 0.0225(10) 0.0186(8) -0.0004(7) 0.0007(7) -0.0008(7) C8 0.0179(9) 0.0220(10) 0.0222(8) -0.0006(7) -0.0010(7) -0.0022(7) C9 0.0288(10) 0.0199(10) 0.0255(9) 0.0006(7) -0.0063(8) 0.0001(8) C10 0.0475(13) 0.0521(14) 0.0218(9) -0.0028(9) -0.0036(9) -0.0029(11) C11 0.0250(10) 0.0319(11) 0.0273(9) 0.0007(8) -0.0039(8) 0.0048(8) C12 0.0398(13) 0.0279(11) 0.0473(12) 0.0136(9) 0.0047(10) 0.0007(9) C13 0.0250(10) 0.0283(10) 0.0255(9) -0.0072(8) -0.0017(7) -0.0004(8) C14 0.0468(14) 0.0257(11) 0.0437(11) 0.0012(9) 0.0057(10) -0.0083(10) O1 0.0214(6) 0.0214(6) 0.0204(6) -0.0033(5) -0.0034(5) 0.0063(5) O2 0.0222(6) 0.0183(7) 0.0211(6) -0.0042(5) -0.0022(5) 0.0023(5) O3 0.0366(8) 0.0300(8) 0.0256(7) 0.0040(5) -0.0036(6) -0.0137(6) O4 0.0510(10) 0.0483(9) 0.0284(7) -0.0058(7) -0.0071(7) -0.0241(8) O5 0.0334(8) 0.0413(8) 0.0211(6) -0.0057(6) -0.0013(5) -0.0063(6) O6 0.0480(9) 0.0272(8) 0.0344(7) -0.0072(6) -0.0136(6) 0.0142(7) O7 0.0245(7) 0.0235(7) 0.0250(6) 0.0032(5) 0.0031(5) -0.0015(5) O8 0.0247(7) 0.0233(7) 0.0293(6) -0.0008(5) 0.0042(5) -0.0038(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 C1 O3 1.425(2) . ? C1 C9 1.530(2) . ? C1 C2 1.532(2) . ? C1 C6 1.535(2) . ? C2 C3 1.519(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O1 1.434(2) . ? C3 C4 1.511(2) . ? C3 H3A 1.0000 . ? C4 O2 1.4406(19) . ? C4 C5 1.516(3) . ? C4 H4A 1.0000 . ? C5 O6 1.412(2) . ? C5 C6 1.527(2) . ? C5 H5A 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O7 1.411(2) . ? C7 O1 1.430(2) . ? C7 C11 1.506(2) . ? C7 C8 1.552(2) . ? C8 O8 1.413(2) . ? C8 O2 1.430(2) . ? C8 C13 1.518(2) . ? C9 O4 1.201(2) . ? C9 O5 1.329(2) . ? C10 O5 1.455(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O7 1.421(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O8 1.425(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O3 H3 0.8400 . ? O6 H6 0.8400 . ? 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 O3 C1 C9 107.27(14) . . ? O3 C1 C2 109.07(13) . . ? C9 C1 C2 111.59(15) . . ? O3 C1 C6 109.29(15) . . ? C9 C1 C6 108.35(14) . . ? C2 C1 C6 111.16(14) . . ? C3 C2 C1 110.04(14) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? O1 C3 C4 110.60(13) . . ? O1 C3 C2 107.84(13) . . ? C4 C3 C2 109.71(14) . . ? O1 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? O2 C4 C3 110.07(13) . . ? O2 C4 C5 108.64(13) . . ? C3 C4 C5 109.12(13) . . ? O2 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? O6 C5 C4 113.57(15) . . ? O6 C5 C6 105.93(14) . . ? C4 C5 C6 108.60(14) . . ? O6 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? C5 C6 C1 113.57(14) . . ? C5 C6 H6A 108.9 . . ? C1 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C1 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? O7 C7 O1 110.60(14) . . ? O7 C7 C11 113.03(14) . . ? O1 C7 C11 105.47(14) . . ? O7 C7 C8 103.98(14) . . ? O1 C7 C8 110.15(13) . . ? C11 C7 C8 113.71(15) . . ? O8 C8 O2 110.49(13) . . ? O8 C8 C13 112.46(14) . . ? O2 C8 C13 105.97(14) . . ? O8 C8 C7 104.71(13) . . ? O2 C8 C7 110.18(13) . . ? C13 C8 C7 113.12(14) . . ? O4 C9 O5 124.76(16) . . ? O4 C9 C1 122.54(17) . . ? O5 C9 C1 112.67(15) . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O7 C12 H12A 109.5 . . ? O7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O8 C14 H14A 109.5 . . ? O8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 O1 C3 112.25(13) . . ? C8 O2 C4 112.45(12) . . ? C1 O3 H3 109.5 . . ? C9 O5 C10 115.50(15) . . ? C5 O6 H6 109.5 . . ? C7 O7 C12 116.85(15) . . ? C8 O8 C14 116.59(14) . . ? 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 O3 C1 C2 C3 -68.49(18) . . . . ? C9 C1 C2 C3 173.17(15) . . . . ? C6 C1 C2 C3 52.08(19) . . . . ? C1 C2 C3 O1 179.26(14) . . . . ? C1 C2 C3 C4 -60.22(18) . . . . ? O1 C3 C4 O2 -56.63(17) . . . . ? C2 C3 C4 O2 -175.48(14) . . . . ? O1 C3 C4 C5 -175.76(13) . . . . ? C2 C3 C4 C5 65.40(18) . . . . ? O2 C4 C5 O6 61.35(18) . . . . ? C3 C4 C5 O6 -178.63(15) . . . . ? O2 C4 C5 C6 178.92(14) . . . . ? C3 C4 C5 C6 -61.07(18) . . . . ? O6 C5 C6 C1 176.87(15) . . . . ? C4 C5 C6 C1 54.54(19) . . . . ? O3 C1 C6 C5 69.91(18) . . . . ? C9 C1 C6 C5 -173.51(15) . . . . ? C2 C1 C6 C5 -50.5(2) . . . . ? O7 C7 C8 O8 176.80(12) . . . . ? O1 C7 C8 O8 -64.68(16) . . . . ? C11 C7 C8 O8 53.45(17) . . . . ? O7 C7 C8 O2 -64.39(16) . . . . ? O1 C7 C8 O2 54.14(17) . . . . ? C11 C7 C8 O2 172.27(14) . . . . ? O7 C7 C8 C13 54.01(18) . . . . ? O1 C7 C8 C13 172.53(14) . . . . ? C11 C7 C8 C13 -69.34(19) . . . . ? O3 C1 C9 O4 7.0(3) . . . . ? C2 C1 C9 O4 126.4(2) . . . . ? C6 C1 C9 O4 -110.9(2) . . . . ? O3 C1 C9 O5 -174.84(15) . . . . ? C2 C1 C9 O5 -55.4(2) . . . . ? C6 C1 C9 O5 67.3(2) . . . . ? O7 C7 O1 C3 58.52(18) . . . . ? C11 C7 O1 C3 -178.95(13) . . . . ? C8 C7 O1 C3 -55.85(17) . . . . ? C4 C3 O1 C7 57.68(17) . . . . ? C2 C3 O1 C7 177.64(13) . . . . ? O8 C8 O2 C4 59.56(17) . . . . ? C13 C8 O2 C4 -178.36(13) . . . . ? C7 C8 O2 C4 -55.66(17) . . . . ? C3 C4 O2 C8 57.16(17) . . . . ? C5 C4 O2 C8 176.58(13) . . . . ? O4 C9 O5 C10 2.3(3) . . . . ? C1 C9 O5 C10 -175.88(16) . . . . ? O1 C7 O7 C12 64.64(19) . . . . ? C11 C7 O7 C12 -53.4(2) . . . . ? C8 C7 O7 C12 -177.14(14) . . . . ? O2 C8 O8 C14 57.65(18) . . . . ? C13 C8 O8 C14 -60.53(19) . . . . ? C7 C8 O8 C14 176.26(14) . . . . ? loop_ _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 O3 H3 O4 0.84 2.11 2.6265(17) 119.3 . O3 H3 O2 0.84 2.65 3.1664(16) 121.5 3_546 O6 H6 O3 0.84 2.02 2.8192(18) 159.9 3_556 O6 H6 O2 0.84 2.48 2.8811(17) 110.2 . # Attachment '5017_web_deposit_cif_file_3_AbhishekBanerjee_1302613529.cif' data_s1 _database_code_depnum_ccdc_archive 'CCDC 821574' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 O4' _chemical_formula_weight 260.28 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7884(5) _cell_length_b 9.8407(4) _cell_length_c 17.4343(10) _cell_angle_alpha 79.265(3) _cell_angle_beta 85.517(4) _cell_angle_gamma 66.444(3) _cell_volume 1357.94(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3046 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 20.95 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9612 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41389 _diffrn_reflns_av_R_equivalents 0.0973 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 24.71 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 4616 _reflns_number_gt 2573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. Acidic H-atoms involved in H-bonding dimer formation were located on a Fourier map and refined freely. The remaining H-atoms were placed in calculated positions using a riding model. ; _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^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4616 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.325 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.050 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 C1 C -0.6520(3) 0.6353(2) 0.65429(14) 0.0315(6) Uani 1 1 d . . . C2 C -0.6889(3) 0.5602(3) 0.72558(14) 0.0333(6) Uani 1 1 d . . . H2A H -0.6199 0.4580 0.7435 0.040 Uiso 1 1 calc R . . C3 C -0.8232(3) 0.6330(2) 0.76945(13) 0.0305(6) Uani 1 1 d . . . C4 C -0.9285(3) 0.7838(2) 0.74251(14) 0.0306(6) Uani 1 1 d . . . C5 C -0.8951(3) 0.8571(3) 0.67239(14) 0.0362(6) Uani 1 1 d . . . H5A H -0.9662 0.9583 0.6537 0.043 Uiso 1 1 calc R . . C6 C -0.7580(3) 0.7837(3) 0.62904(14) 0.0377(6) Uani 1 1 d . . . H6A H -0.7356 0.8358 0.5808 0.045 Uiso 1 1 calc R . . C7 C -0.5075(3) 0.5625(3) 0.60791(14) 0.0352(6) Uani 1 1 d . . . H7A H -0.4861 0.6254 0.5638 0.042 Uiso 1 1 calc R . . C8 C -0.4008(3) 0.4189(3) 0.61911(14) 0.0356(6) Uani 1 1 d . . . H8A H -0.4197 0.3514 0.6616 0.043 Uiso 1 1 calc R . . C9 C -0.2571(3) 0.3613(3) 0.56923(14) 0.0337(6) Uani 1 1 d . . . C10 C -0.7550(3) 0.4221(2) 0.87349(14) 0.0378(6) Uani 1 1 d . . . H10A H -0.6410 0.4182 0.8752 0.045 Uiso 1 1 calc R . . H10B H -0.7536 0.3486 0.8414 0.045 Uiso 1 1 calc R . . C11 C -0.8143(3) 0.3859(3) 0.95330(15) 0.0476(7) Uani 1 1 d . . . H11A H -0.8292 0.4530 0.9886 0.057 Uiso 1 1 calc R . . C12 C -0.8476(4) 0.2667(3) 0.97804(19) 0.0741(10) Uani 1 1 d . . . H12A H -0.8339 0.1976 0.9440 0.089 Uiso 1 1 calc R . . H12B H -0.8854 0.2492 1.0300 0.089 Uiso 1 1 calc R . . C13 C -1.1518(3) 1.0052(2) 0.77369(15) 0.0392(7) Uani 1 1 d . . . H13A H -1.2279 1.0293 0.7296 0.047 Uiso 1 1 calc R . . H13B H -1.0775 1.0597 0.7594 0.047 Uiso 1 1 calc R . . C14 C -1.2473(4) 1.0489(3) 0.84546(17) 0.0481(7) Uani 1 1 d . . . H14A H -1.1860 1.0337 0.8910 0.058 Uiso 1 1 calc R . . C15 C -1.4080(4) 1.1061(3) 0.85090(19) 0.0618(9) Uani 1 1 d . . . H15A H -1.4739 1.1231 0.8067 0.074 Uiso 1 1 calc R . . H15B H -1.4599 1.1311 0.8991 0.074 Uiso 1 1 calc R . . O1 O -0.2284(2) 0.45309(18) 0.51320(10) 0.0444(5) Uani 1 1 d . . . H1O1 H -0.115(5) 0.400(4) 0.480(2) 0.131(14) Uiso 1 1 d . . . O2 O -0.1642(2) 0.22311(18) 0.58232(10) 0.0498(5) Uani 1 1 d . . . O3 O -0.86680(19) 0.57110(16) 0.84041(9) 0.0371(4) Uani 1 1 d . . . O4 O -1.05627(19) 0.84534(16) 0.79138(9) 0.0390(5) Uani 1 1 d . . . C16 C 0.5404(3) -0.0606(3) 0.36435(14) 0.0318(6) Uani 1 1 d . . . C17 C 0.5796(3) 0.0127(3) 0.29311(14) 0.0326(6) Uani 1 1 d . . . H17A H 0.5080 0.1131 0.2731 0.039 Uiso 1 1 calc R . . C18 C 0.7206(3) -0.0592(2) 0.25188(14) 0.0316(6) Uani 1 1 d . . . C19 C 0.8278(3) -0.2079(2) 0.28164(14) 0.0313(6) Uani 1 1 d . . . C20 C 0.7903(3) -0.2811(3) 0.35063(14) 0.0362(6) Uani 1 1 d . . . H20A H 0.8619 -0.3815 0.3705 0.043 Uiso 1 1 calc R . . C21 C 0.6477(3) -0.2082(3) 0.39121(15) 0.0386(6) Uani 1 1 d . . . H21A H 0.6224 -0.2603 0.4387 0.046 Uiso 1 1 calc R . . C22 C 0.3924(3) 0.0105(3) 0.40867(14) 0.0350(6) Uani 1 1 d . . . H22A H 0.3707 -0.0522 0.4527 0.042 Uiso 1 1 calc R . . C23 C 0.2831(3) 0.1523(3) 0.39574(14) 0.0375(6) Uani 1 1 d . . . H23A H 0.3021 0.2198 0.3533 0.045 Uiso 1 1 calc R . . C24 C 0.1347(3) 0.2088(3) 0.44396(14) 0.0349(6) Uani 1 1 d . . . C25 C 0.6569(3) 0.1505(3) 0.14784(14) 0.0390(6) Uani 1 1 d . . . H25A H 0.6333 0.2200 0.1857 0.047 Uiso 1 1 calc R . . H25B H 0.5506 0.1494 0.1336 0.047 Uiso 1 1 calc R . . C26 C 0.7389(4) 0.2012(3) 0.07709(18) 0.0567(8) Uani 1 1 d . . . H26A H 0.8528 0.1829 0.0816 0.068 Uiso 1 1 calc R . . C27 C 0.6719(5) 0.2660(4) 0.01184(19) 0.0781(10) Uani 1 1 d . . . H27A H 0.5582 0.2867 0.0045 0.094 Uiso 1 1 calc R . . H27B H 0.7348 0.2942 -0.0301 0.094 Uiso 1 1 calc R . . C28 C 1.0763(3) -0.4204(2) 0.26122(14) 0.0347(6) Uani 1 1 d . . . H28A H 1.0200 -0.4899 0.2618 0.042 Uiso 1 1 calc R . . H28B H 1.1163 -0.4324 0.3146 0.042 Uiso 1 1 calc R . . C29 C 1.2170(3) -0.4536(3) 0.20534(15) 0.0435(7) Uani 1 1 d . . . H29A H 1.2793 -0.3925 0.1991 0.052 Uiso 1 1 calc R . . C30 C 1.2607(3) -0.5610(3) 0.16424(16) 0.0542(8) Uani 1 1 d . . . H30A H 1.2010 -0.6241 0.1691 0.065 Uiso 1 1 calc R . . H30B H 1.3524 -0.5764 0.1293 0.065 Uiso 1 1 calc R . . O5 O 0.1058(2) 0.11484(18) 0.49813(10) 0.0440(5) Uani 1 1 d . . . H1O5 H -0.009(5) 0.165(4) 0.529(2) 0.142(15) Uiso 1 1 d . . . O6 O 0.0405(2) 0.34665(18) 0.43029(10) 0.0464(5) Uani 1 1 d . . . O7 O 0.76677(19) 0.00211(17) 0.18176(9) 0.0403(5) Uani 1 1 d . . . O8 O 0.96328(19) -0.26708(16) 0.23565(9) 0.0381(4) 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 C1 0.0302(15) 0.0317(14) 0.0312(15) -0.0053(11) 0.0031(12) -0.0114(12) C2 0.0314(15) 0.0266(13) 0.0380(16) -0.0061(11) 0.0007(12) -0.0073(11) C3 0.0305(15) 0.0302(13) 0.0292(15) -0.0040(11) 0.0022(12) -0.0112(11) C4 0.0268(14) 0.0295(13) 0.0339(15) -0.0060(11) 0.0026(12) -0.0098(11) C5 0.0359(16) 0.0256(13) 0.0403(16) -0.0033(12) -0.0006(13) -0.0059(11) C6 0.0389(16) 0.0350(14) 0.0349(15) -0.0023(12) 0.0021(13) -0.0119(12) C7 0.0358(16) 0.0378(15) 0.0305(15) -0.0040(12) 0.0007(12) -0.0137(12) C8 0.0336(15) 0.0372(15) 0.0334(15) -0.0066(12) 0.0059(12) -0.0122(12) C9 0.0299(15) 0.0345(15) 0.0346(16) -0.0096(12) 0.0012(12) -0.0090(12) C10 0.0364(15) 0.0314(14) 0.0359(16) 0.0001(11) 0.0012(12) -0.0059(12) C11 0.0421(17) 0.0459(17) 0.0394(17) 0.0026(13) 0.0051(13) -0.0066(13) C12 0.073(2) 0.060(2) 0.071(2) 0.0095(17) 0.0220(18) -0.0204(18) C13 0.0327(15) 0.0231(13) 0.0521(18) -0.0038(12) 0.0012(13) -0.0023(11) C14 0.045(2) 0.0348(15) 0.0539(19) -0.0112(13) -0.0008(15) -0.0034(13) C15 0.051(2) 0.0520(18) 0.081(2) -0.0301(17) 0.0130(17) -0.0128(16) O1 0.0430(12) 0.0371(10) 0.0429(12) -0.0007(9) 0.0124(9) -0.0100(9) O2 0.0487(12) 0.0352(11) 0.0490(12) -0.0031(9) 0.0168(9) -0.0043(9) O3 0.0348(10) 0.0287(9) 0.0368(11) -0.0005(8) 0.0057(8) -0.0044(8) O4 0.0352(11) 0.0277(9) 0.0439(11) -0.0057(8) 0.0089(9) -0.0035(8) C16 0.0314(15) 0.0313(14) 0.0329(15) -0.0085(11) 0.0041(12) -0.0120(12) C17 0.0287(15) 0.0279(13) 0.0368(15) -0.0061(11) 0.0006(12) -0.0065(11) C18 0.0322(15) 0.0301(13) 0.0313(15) -0.0017(11) 0.0012(12) -0.0128(12) C19 0.0251(14) 0.0308(14) 0.0374(16) -0.0115(12) 0.0065(12) -0.0089(11) C20 0.0360(16) 0.0284(14) 0.0381(16) -0.0029(12) 0.0034(13) -0.0082(12) C21 0.0389(16) 0.0365(15) 0.0365(16) -0.0017(12) 0.0065(13) -0.0138(13) C22 0.0343(15) 0.0363(15) 0.0333(15) -0.0070(12) 0.0073(12) -0.0136(12) C23 0.0381(16) 0.0379(15) 0.0355(15) -0.0068(12) 0.0094(13) -0.0154(13) C24 0.0324(15) 0.0365(15) 0.0350(16) -0.0081(13) 0.0022(12) -0.0122(13) C25 0.0389(16) 0.0315(14) 0.0382(16) 0.0015(11) 0.0009(13) -0.0083(12) C26 0.0515(19) 0.0451(17) 0.055(2) 0.0059(15) 0.0052(16) -0.0069(14) C27 0.091(3) 0.076(2) 0.051(2) 0.0022(19) 0.005(2) -0.023(2) C28 0.0321(15) 0.0285(13) 0.0385(15) -0.0055(11) 0.0006(12) -0.0067(11) C29 0.0362(16) 0.0366(15) 0.0516(18) -0.0066(13) 0.0060(14) -0.0097(12) C30 0.0420(18) 0.0458(17) 0.0572(19) -0.0082(15) 0.0097(15) -0.0013(14) O5 0.0399(12) 0.0391(10) 0.0413(11) 0.0004(9) 0.0118(9) -0.0085(9) O6 0.0418(11) 0.0326(10) 0.0529(12) -0.0036(9) 0.0114(9) -0.0062(9) O7 0.0361(10) 0.0311(9) 0.0385(11) 0.0023(8) 0.0108(8) -0.0030(8) O8 0.0347(10) 0.0270(9) 0.0422(11) -0.0036(8) 0.0082(8) -0.0038(8) _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 C1 C6 1.390(3) . ? C1 C2 1.408(3) . ? C1 C7 1.451(3) . ? C2 C3 1.370(3) . ? C2 H2A 0.9500 . ? C3 O3 1.371(3) . ? C3 C4 1.411(3) . ? C4 O4 1.361(3) . ? C4 C5 1.373(3) . ? C5 C6 1.382(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.334(3) . ? C7 H7A 0.9500 . ? C8 C9 1.454(3) . ? C8 H8A 0.9500 . ? C9 O2 1.262(3) . ? C9 O1 1.284(3) . ? C10 O3 1.439(2) . ? C10 C11 1.478(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.309(4) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C12 H12B 0.9500 . ? C13 O4 1.442(2) . ? C13 C14 1.484(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.298(3) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? O1 H1O1 1.09(4) . ? C16 C21 1.392(3) . ? C16 C17 1.407(3) . ? C16 C22 1.447(3) . ? C17 C18 1.379(3) . ? C17 H17A 0.9500 . ? C18 O7 1.366(3) . ? C18 C19 1.411(3) . ? C19 O8 1.367(3) . ? C19 C20 1.371(3) . ? C20 C21 1.385(3) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.329(3) . ? C22 H22A 0.9500 . ? C23 C24 1.463(3) . ? C23 H23A 0.9500 . ? C24 O6 1.263(3) . ? C24 O5 1.280(3) . ? C25 O7 1.434(3) . ? C25 C26 1.486(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.258(4) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C27 H27B 0.9500 . ? C28 O8 1.443(2) . ? C28 C29 1.481(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.301(3) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C30 H30B 0.9500 . ? O5 H1O5 1.08(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 C6 C1 C2 118.0(2) . . ? C6 C1 C7 120.1(2) . . ? C2 C1 C7 121.9(2) . . ? C3 C2 C1 120.8(2) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C2 C3 O3 125.1(2) . . ? C2 C3 C4 120.0(2) . . ? O3 C3 C4 114.8(2) . . ? O4 C4 C5 125.5(2) . . ? O4 C4 C3 114.9(2) . . ? C5 C4 C3 119.6(2) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C5 C6 C1 121.6(2) . . ? C5 C6 H6A 119.2 . . ? C1 C6 H6A 119.2 . . ? C8 C7 C1 128.5(2) . . ? C8 C7 H7A 115.7 . . ? C1 C7 H7A 115.7 . . ? C7 C8 C9 122.9(2) . . ? C7 C8 H8A 118.5 . . ? C9 C8 H8A 118.5 . . ? O2 C9 O1 122.0(2) . . ? O2 C9 C8 119.2(2) . . ? O1 C9 C8 118.7(2) . . ? O3 C10 C11 107.59(19) . . ? O3 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? O3 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? C12 C11 C10 123.7(3) . . ? C12 C11 H11A 118.1 . . ? C10 C11 H11A 118.1 . . ? C11 C12 H12A 120.0 . . ? C11 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? O4 C13 C14 106.35(19) . . ? O4 C13 H13A 110.5 . . ? C14 C13 H13A 110.5 . . ? O4 C13 H13B 110.5 . . ? C14 C13 H13B 110.5 . . ? H13A C13 H13B 108.7 . . ? C15 C14 C13 125.2(3) . . ? C15 C14 H14A 117.4 . . ? C13 C14 H14A 117.4 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? C9 O1 H1O1 113.1(19) . . ? C3 O3 C10 116.80(17) . . ? C4 O4 C13 117.60(18) . . ? C21 C16 C17 117.7(2) . . ? C21 C16 C22 119.8(2) . . ? C17 C16 C22 122.4(2) . . ? C18 C17 C16 120.9(2) . . ? C18 C17 H17A 119.5 . . ? C16 C17 H17A 119.5 . . ? O7 C18 C17 124.9(2) . . ? O7 C18 C19 115.4(2) . . ? C17 C18 C19 119.7(2) . . ? O8 C19 C20 125.7(2) . . ? O8 C19 C18 114.3(2) . . ? C20 C19 C18 120.0(2) . . ? C19 C20 C21 119.8(2) . . ? C19 C20 H20A 120.1 . . ? C21 C20 H20A 120.1 . . ? C20 C21 C16 121.8(2) . . ? C20 C21 H21A 119.1 . . ? C16 C21 H21A 119.1 . . ? C23 C22 C16 128.4(2) . . ? C23 C22 H22A 115.8 . . ? C16 C22 H22A 115.8 . . ? C22 C23 C24 122.8(2) . . ? C22 C23 H23A 118.6 . . ? C24 C23 H23A 118.6 . . ? O6 C24 O5 122.9(2) . . ? O6 C24 C23 119.2(2) . . ? O5 C24 C23 117.9(2) . . ? O7 C25 C26 108.0(2) . . ? O7 C25 H25A 110.1 . . ? C26 C25 H25A 110.1 . . ? O7 C25 H25B 110.1 . . ? C26 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? C27 C26 C25 126.2(3) . . ? C27 C26 H26A 116.9 . . ? C25 C26 H26A 116.9 . . ? C26 C27 H27A 120.0 . . ? C26 C27 H27B 120.0 . . ? H27A C27 H27B 120.0 . . ? O8 C28 C29 107.00(18) . . ? O8 C28 H28A 110.3 . . ? C29 C28 H28A 110.3 . . ? O8 C28 H28B 110.3 . . ? C29 C28 H28B 110.3 . . ? H28A C28 H28B 108.6 . . ? C30 C29 C28 124.2(2) . . ? C30 C29 H29A 117.9 . . ? C28 C29 H29A 117.9 . . ? C29 C30 H30A 120.0 . . ? C29 C30 H30B 120.0 . . ? H30A C30 H30B 120.0 . . ? C24 O5 H1O5 113(2) . . ? C18 O7 C25 117.06(18) . . ? C19 O8 C28 117.48(17) . . ? 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 C6 C1 C2 C3 -1.5(3) . . . . ? C7 C1 C2 C3 178.0(2) . . . . ? C1 C2 C3 O3 -178.2(2) . . . . ? C1 C2 C3 C4 1.4(3) . . . . ? C2 C3 C4 O4 -178.98(19) . . . . ? O3 C3 C4 O4 0.6(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? O3 C3 C4 C5 179.3(2) . . . . ? O4 C4 C5 C6 177.9(2) . . . . ? C3 C4 C5 C6 -0.7(3) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? C2 C1 C6 C5 0.6(3) . . . . ? C7 C1 C6 C5 -178.9(2) . . . . ? C6 C1 C7 C8 -173.8(2) . . . . ? C2 C1 C7 C8 6.7(4) . . . . ? C1 C7 C8 C9 -178.0(2) . . . . ? C7 C8 C9 O2 -178.1(2) . . . . ? C7 C8 C9 O1 2.1(4) . . . . ? O3 C10 C11 C12 124.8(3) . . . . ? O4 C13 C14 C15 -117.8(3) . . . . ? C2 C3 O3 C10 4.9(3) . . . . ? C4 C3 O3 C10 -174.64(19) . . . . ? C11 C10 O3 C3 172.9(2) . . . . ? C5 C4 O4 C13 -8.6(3) . . . . ? C3 C4 O4 C13 170.0(2) . . . . ? C14 C13 O4 C4 -164.2(2) . . . . ? C21 C16 C17 C18 -0.6(3) . . . . ? C22 C16 C17 C18 -179.1(2) . . . . ? C16 C17 C18 O7 178.8(2) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? O7 C18 C19 O8 0.7(3) . . . . ? C17 C18 C19 O8 -179.96(19) . . . . ? O7 C18 C19 C20 -178.3(2) . . . . ? C17 C18 C19 C20 1.0(3) . . . . ? O8 C19 C20 C21 -179.4(2) . . . . ? C18 C19 C20 C21 -0.5(4) . . . . ? C19 C20 C21 C16 -0.6(4) . . . . ? C17 C16 C21 C20 1.1(4) . . . . ? C22 C16 C21 C20 179.7(2) . . . . ? C21 C16 C22 C23 174.4(2) . . . . ? C17 C16 C22 C23 -7.1(4) . . . . ? C16 C22 C23 C24 177.9(2) . . . . ? C22 C23 C24 O6 176.8(2) . . . . ? C22 C23 C24 O5 -3.9(4) . . . . ? O7 C25 C26 C27 135.5(3) . . . . ? O8 C28 C29 C30 -121.2(3) . . . . ? C17 C18 O7 C25 -2.1(3) . . . . ? C19 C18 O7 C25 177.2(2) . . . . ? C26 C25 O7 C18 174.0(2) . . . . ? C20 C19 O8 C28 0.7(3) . . . . ? C18 C19 O8 C28 -178.27(19) . . . . ? C29 C28 O8 C19 -175.90(19) . . . . ? loop_ _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 O1 H1O1 O6 1.09(4) 1.52(4) 2.612(2) 172(3) . O5 H1O5 O2 1.08(4) 1.56(4) 2.633(2) 173(3) .