# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_coeditor_code ? _journal_date_accepted ? _journal_date_from_coeditor ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Ken Takaki' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; 'Kazuhiro Shiraishi' '' '' 'Kosuke Okinaga' '' '' 'Shintaro Takahashi' '' '' 'Kimihiro Komeyama' '' '' _publ_contact_author_email ktakaki@hiroshima-u.ac.jp _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Ken Takaki' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; data_3,4-dihydro-2H-pyran-2-one/4m _database_code_depnum_ccdc_archive 'CCDC 825847' #TrackingRef '- Product 4m .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H30 Cl2 O3' _chemical_formula_weight 593.51 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 9.707(5) _cell_length_b 10.540(6) _cell_length_c 15.245(8) _cell_angle_alpha 98.505(8) _cell_angle_beta 103.665(7) _cell_angle_gamma 101.424(7) _cell_volume 1454.2(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 3571 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.45 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9376 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 8.333 _diffrn_reflns_number 7117 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5280 _reflns_number_gt 4086 _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. ; _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^)+(0.1070P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5280 _refine_ls_number_parameters 499 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1522 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.18606(7) 0.98999(7) 0.56556(4) 0.0259(2) Uani 1 1 d . . . Cl2 Cl -0.17796(6) -0.78434(7) -0.00150(4) 0.0229(2) Uani 1 1 d . . . O1 O 0.23661(17) 0.38357(19) 0.42235(11) 0.0204(4) Uani 1 1 d . . . O2 O 0.37418(18) 0.2426(2) 0.41819(12) 0.0233(5) Uani 1 1 d . . . O3 O -0.09887(18) -0.1871(2) 0.25101(12) 0.0244(5) Uani 1 1 d . . . C1 C 0.1122(2) 0.4277(3) 0.38346(17) 0.0192(6) Uani 1 1 d . . . C2 C 0.0000(3) 0.3457(3) 0.31940(17) 0.0192(6) Uani 1 1 d . . . C3 C 0.0065(2) 0.2080(3) 0.28255(18) 0.0202(6) Uani 1 1 d . . . C4 C 0.1647(2) 0.2045(3) 0.28511(17) 0.0176(6) Uani 1 1 d . . . C5 C 0.2666(2) 0.2733(3) 0.37889(17) 0.0175(6) Uani 1 1 d . . . C6 C 0.1837(2) 0.0658(3) 0.25093(16) 0.0160(5) Uani 1 1 d . . . C7 C 0.1814(3) -0.0245(3) 0.32212(17) 0.0185(6) Uani 1 1 d . . . C8 C 0.1573(3) -0.1684(3) 0.27763(17) 0.0184(6) Uani 1 1 d . . . C9 C -0.0029(2) -0.2407(3) 0.23783(16) 0.0176(6) Uani 1 1 d . . . C10 C 0.1294(3) 0.5649(3) 0.42709(16) 0.0177(6) Uani 1 1 d . . . C11 C 0.0078(3) 0.6203(3) 0.42486(17) 0.0208(6) Uani 1 1 d . . . C12 C 0.0245(3) 0.7490(3) 0.46583(17) 0.0203(6) Uani 1 1 d . . . C13 C 0.1638(3) 0.8276(3) 0.51105(17) 0.0216(6) Uani 1 1 d . . . C14 C 0.2859(3) 0.7761(3) 0.51433(18) 0.0228(6) Uani 1 1 d . . . C15 C 0.2678(3) 0.6466(3) 0.47271(17) 0.0214(6) Uani 1 1 d . . . C16 C 0.3152(2) 0.0745(3) 0.21155(16) 0.0169(6) Uani 1 1 d . . . C17 C 0.4465(3) 0.0562(3) 0.25989(17) 0.0184(6) Uani 1 1 d . . . C18 C 0.5706(3) 0.0726(3) 0.22675(17) 0.0209(6) Uani 1 1 d . . . C19 C 0.5652(3) 0.1063(3) 0.14295(18) 0.0205(6) Uani 1 1 d . . . C20 C 0.4225(3) 0.1537(3) -0.00056(17) 0.0194(6) Uani 1 1 d . . . C21 C 0.2952(3) 0.1709(3) -0.05345(17) 0.0208(6) Uani 1 1 d . . . C22 C 0.1710(3) 0.1565(3) -0.01988(17) 0.0210(6) Uani 1 1 d . . . C23 C 0.1751(2) 0.1268(3) 0.06540(17) 0.0170(6) Uani 1 1 d . . . C24 C 0.3062(2) 0.1081(3) 0.12221(16) 0.0161(5) Uani 1 1 d . . . C25 C 0.4315(2) 0.1237(3) 0.08851(16) 0.0167(5) Uani 1 1 d . . . C26 C -0.0410(2) -0.3777(3) 0.18228(16) 0.0165(6) Uani 1 1 d . . . C27 C 0.0629(3) -0.4392(3) 0.15595(17) 0.0194(6) Uani 1 1 d . . . C28 C 0.0226(3) -0.5623(3) 0.10077(18) 0.0186(6) Uani 1 1 d . . . C29 C -0.1254(2) -0.6303(3) 0.07041(17) 0.0185(6) Uani 1 1 d . . . C30 C -0.2302(3) -0.5733(3) 0.09830(18) 0.0212(6) Uani 1 1 d . . . C31 C -0.1874(3) -0.4484(3) 0.15358(17) 0.0200(6) Uani 1 1 d . . . C32 C 0.4407(3) 0.4709(3) 0.1703(2) 0.0273(7) Uani 1 1 d . . . C33 C 0.4447(3) 0.5994(3) 0.1634(2) 0.0305(8) Uani 1 1 d . . . C34 C 0.5009(3) 0.6992(4) 0.2408(3) 0.0391(9) Uani 1 1 d . . . C35 C 0.5531(4) 0.6685(4) 0.3269(3) 0.0430(9) Uani 1 1 d . . . C36 C 0.5490(3) 0.5397(4) 0.3335(2) 0.0369(8) Uani 1 1 d . . . C37 C 0.4935(3) 0.4405(3) 0.2553(2) 0.0291(7) Uani 1 1 d . . . H1 H -0.085(3) 0.380(3) 0.2992(19) 0.023(7) Uiso 1 1 d . . . H2 H -0.035(3) 0.145(3) 0.3170(19) 0.023(7) Uiso 1 1 d . . . H3 H -0.055(3) 0.171(3) 0.2185(19) 0.018(7) Uiso 1 1 d . . . H4 H 0.193(3) 0.265(3) 0.2439(19) 0.025(7) Uiso 1 1 d . . . H5 H 0.097(3) 0.019(3) 0.1980(18) 0.016(7) Uiso 1 1 d . . . H6 H 0.272(3) 0.010(3) 0.3758(18) 0.019(7) Uiso 1 1 d . . . H7 H 0.100(3) -0.014(3) 0.3519(18) 0.021(7) Uiso 1 1 d . . . H8 H 0.200(3) -0.180(3) 0.2245(19) 0.019(7) Uiso 1 1 d . . . H9 H 0.196(3) -0.229(3) 0.3218(19) 0.024(7) Uiso 1 1 d . . . H10 H -0.087(3) 0.557(3) 0.3896(17) 0.014(6) Uiso 1 1 d . . . H11 H -0.059(3) 0.786(3) 0.4653(18) 0.021(7) Uiso 1 1 d . . . H12 H 0.386(3) 0.836(3) 0.542(2) 0.030(8) Uiso 1 1 d . . . H13 H 0.354(3) 0.613(3) 0.473(2) 0.031(8) Uiso 1 1 d . . . H14 H 0.457(3) 0.039(3) 0.322(2) 0.025(7) Uiso 1 1 d . . . H15 H 0.664(3) 0.058(3) 0.264(2) 0.035(8) Uiso 1 1 d . . . H16 H 0.649(3) 0.118(3) 0.1220(17) 0.013(6) Uiso 1 1 d . . . H17 H 0.508(3) 0.162(3) -0.0222(17) 0.012(6) Uiso 1 1 d . . . H18 H 0.291(3) 0.183(3) -0.1178(18) 0.015(6) Uiso 1 1 d . . . H19 H 0.077(3) 0.163(3) -0.058(2) 0.033(8) Uiso 1 1 d . . . H20 H 0.088(3) 0.117(3) 0.0886(17) 0.011(6) Uiso 1 1 d . . . H21 H 0.161(3) -0.391(3) 0.1757(18) 0.021(7) Uiso 1 1 d . . . H22 H 0.090(3) -0.599(3) 0.0840(19) 0.024(7) Uiso 1 1 d . . . H23 H -0.333(3) -0.622(3) 0.079(2) 0.033(8) Uiso 1 1 d . . . H24 H -0.255(4) -0.409(4) 0.173(2) 0.038(9) Uiso 1 1 d . . . H25 H 0.402(3) 0.396(4) 0.117(2) 0.035(9) Uiso 1 1 d . . . H26 H 0.415(4) 0.614(4) 0.106(2) 0.043(9) Uiso 1 1 d . . . H27 H 0.504(3) 0.783(4) 0.241(2) 0.036(9) Uiso 1 1 d . . . H28 H 0.591(4) 0.735(4) 0.379(3) 0.047(10) Uiso 1 1 d . . . H29 H 0.590(4) 0.522(4) 0.397(3) 0.058(11) Uiso 1 1 d . . . H30 H 0.491(3) 0.350(4) 0.258(2) 0.033(9) 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 Cl1 0.0311(4) 0.0243(4) 0.0268(4) 0.0122(3) 0.0046(3) 0.0159(3) Cl2 0.0163(3) 0.0237(4) 0.0309(4) 0.0084(3) 0.0078(2) 0.0060(3) O1 0.0190(8) 0.0227(12) 0.0223(9) 0.0092(8) 0.0010(7) 0.0140(8) O2 0.0171(8) 0.0259(13) 0.0287(10) 0.0092(9) 0.0010(7) 0.0130(8) O3 0.0189(8) 0.0285(13) 0.0298(10) 0.0114(9) 0.0042(7) 0.0142(8) C1 0.0155(11) 0.0304(18) 0.0210(12) 0.0176(12) 0.0069(9) 0.0150(11) C2 0.0151(11) 0.0250(18) 0.0237(13) 0.0147(12) 0.0063(9) 0.0111(11) C3 0.0138(11) 0.0265(18) 0.0234(13) 0.0113(12) 0.0040(10) 0.0083(11) C4 0.0135(11) 0.0195(16) 0.0235(13) 0.0123(12) 0.0054(9) 0.0061(10) C5 0.0125(11) 0.0221(17) 0.0227(12) 0.0133(12) 0.0067(9) 0.0065(10) C6 0.0140(11) 0.0180(16) 0.0182(12) 0.0103(11) 0.0034(9) 0.0052(10) C7 0.0174(11) 0.0204(17) 0.0211(12) 0.0118(11) 0.0062(10) 0.0058(11) C8 0.0174(11) 0.0217(17) 0.0206(12) 0.0135(12) 0.0061(9) 0.0077(11) C9 0.0182(12) 0.0226(17) 0.0188(12) 0.0163(12) 0.0058(9) 0.0109(11) C10 0.0205(12) 0.0225(17) 0.0182(12) 0.0154(11) 0.0078(9) 0.0127(11) C11 0.0175(12) 0.0294(18) 0.0225(13) 0.0169(12) 0.0071(10) 0.0113(12) C12 0.0235(12) 0.0235(17) 0.0235(13) 0.0163(12) 0.0098(10) 0.0147(12) C13 0.0252(13) 0.0283(18) 0.0175(12) 0.0134(12) 0.0058(10) 0.0141(12) C14 0.0201(12) 0.0241(18) 0.0263(14) 0.0113(12) 0.0015(10) 0.0112(12) C15 0.0194(12) 0.0266(18) 0.0230(13) 0.0125(12) 0.0033(10) 0.0140(12) C16 0.0148(11) 0.0164(16) 0.0214(12) 0.0099(11) 0.0042(9) 0.0049(10) C17 0.0194(12) 0.0182(16) 0.0213(13) 0.0109(11) 0.0041(9) 0.0098(11) C18 0.0164(11) 0.0236(17) 0.0262(13) 0.0120(12) 0.0035(10) 0.0104(11) C19 0.0152(12) 0.0239(18) 0.0275(13) 0.0121(12) 0.0075(10) 0.0093(11) C20 0.0143(11) 0.0246(17) 0.0236(13) 0.0110(12) 0.0082(9) 0.0064(11) C21 0.0206(12) 0.0243(18) 0.0214(13) 0.0123(12) 0.0057(10) 0.0089(11) C22 0.0149(11) 0.0263(18) 0.0247(13) 0.0124(12) 0.0036(9) 0.0085(11) C23 0.0137(11) 0.0184(16) 0.0217(13) 0.0090(11) 0.0049(9) 0.0067(10) C24 0.0146(11) 0.0146(16) 0.0221(12) 0.0092(11) 0.0050(9) 0.0062(10) C25 0.0162(11) 0.0147(15) 0.0215(12) 0.0076(11) 0.0051(9) 0.0061(10) C26 0.0143(11) 0.0198(16) 0.0208(12) 0.0144(11) 0.0049(9) 0.0083(10) C27 0.0129(11) 0.0229(17) 0.0246(13) 0.0124(12) 0.0047(9) 0.0047(11) C28 0.0150(11) 0.0194(17) 0.0261(13) 0.0103(12) 0.0075(10) 0.0081(11) C29 0.0161(11) 0.0225(17) 0.0214(12) 0.0132(12) 0.0060(9) 0.0076(11) C30 0.0124(11) 0.0244(18) 0.0298(14) 0.0129(13) 0.0050(10) 0.0067(11) C31 0.0164(12) 0.0232(17) 0.0265(14) 0.0125(12) 0.0073(10) 0.0116(11) C32 0.0152(12) 0.036(2) 0.0322(16) 0.0081(15) 0.0076(11) 0.0069(12) C33 0.0194(12) 0.043(2) 0.0403(17) 0.0250(17) 0.0129(12) 0.0161(13) C34 0.0288(15) 0.022(2) 0.082(3) 0.0251(19) 0.0297(16) 0.0117(14) C35 0.0352(17) 0.045(3) 0.043(2) -0.0037(18) 0.0147(14) 0.0010(16) C36 0.0322(15) 0.046(3) 0.0343(17) 0.0188(17) 0.0085(12) 0.0060(15) C37 0.0201(13) 0.027(2) 0.0455(18) 0.0191(15) 0.0111(12) 0.0060(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C13 1.736(3) . ? Cl2 C29 1.726(3) . ? O1 C5 1.368(3) . ? O1 C1 1.411(3) . ? O2 C5 1.204(3) . ? O3 C9 1.221(3) . ? C1 C2 1.328(4) . ? C1 C10 1.459(4) . ? C2 C3 1.495(4) . ? C2 H1 0.97(3) . ? C3 C4 1.535(3) . ? C3 H2 0.99(3) . ? C3 H3 0.99(3) . ? C4 C5 1.513(4) . ? C4 C6 1.539(4) . ? C4 H4 1.01(3) . ? C6 C16 1.526(3) . ? C6 C7 1.547(3) . ? C6 H5 1.00(3) . ? C7 C8 1.515(4) . ? C7 H6 1.01(3) . ? C7 H7 1.02(3) . ? C8 C9 1.521(3) . ? C8 H8 1.00(3) . ? C8 H9 1.05(3) . ? C9 C26 1.489(4) . ? C10 C15 1.397(4) . ? C10 C11 1.413(3) . ? C11 C12 1.368(4) . ? C11 H10 1.00(3) . ? C12 C13 1.391(4) . ? C12 H11 0.97(3) . ? C13 C14 1.392(4) . ? C14 C15 1.375(4) . ? C14 H12 1.00(3) . ? C15 H13 0.97(3) . ? C16 C17 1.379(3) . ? C16 C24 1.445(3) . ? C17 C18 1.402(4) . ? C17 H14 0.97(3) . ? C18 C19 1.368(4) . ? C18 H15 1.01(3) . ? C19 C25 1.427(3) . ? C19 H16 0.93(3) . ? C20 C21 1.368(3) . ? C20 C25 1.426(3) . ? C20 H17 0.95(3) . ? C21 C22 1.408(4) . ? C21 H18 1.00(3) . ? C22 C23 1.375(3) . ? C22 H19 0.98(3) . ? C23 C24 1.427(3) . ? C23 H20 0.98(3) . ? C24 C25 1.418(4) . ? C26 C31 1.399(3) . ? C26 C27 1.404(4) . ? C27 C28 1.365(4) . ? C27 H21 0.94(3) . ? C28 C29 1.405(3) . ? C28 H22 0.89(3) . ? C29 C30 1.395(4) . ? C30 C31 1.381(4) . ? C30 H23 0.98(3) . ? C31 H24 0.93(4) . ? C32 C33 1.368(5) . ? C32 C37 1.386(4) . ? C32 H25 0.99(4) . ? C33 C34 1.378(5) . ? C33 H26 0.90(3) . ? C34 C35 1.400(5) . ? C34 H27 0.88(4) . ? C35 C36 1.369(5) . ? C35 H28 0.92(4) . ? C36 C37 1.381(5) . ? C36 H29 1.02(4) . ? C37 H30 0.96(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 C5 O1 C1 121.5(2) . . ? C2 C1 O1 120.3(3) . . ? C2 C1 C10 129.7(2) . . ? O1 C1 C10 109.9(2) . . ? C1 C2 C3 120.9(2) . . ? C1 C2 H1 116.1(18) . . ? C3 C2 H1 122.9(18) . . ? C2 C3 C4 109.8(2) . . ? C2 C3 H2 111.2(18) . . ? C4 C3 H2 111.3(16) . . ? C2 C3 H3 114.2(17) . . ? C4 C3 H3 108.1(16) . . ? H2 C3 H3 102(2) . . ? C5 C4 C3 110.4(2) . . ? C5 C4 C6 113.74(19) . . ? C3 C4 C6 113.9(2) . . ? C5 C4 H4 102.9(16) . . ? C3 C4 H4 105.2(16) . . ? C6 C4 H4 109.8(18) . . ? O2 C5 O1 116.5(2) . . ? O2 C5 C4 126.4(3) . . ? O1 C5 C4 117.08(19) . . ? C16 C6 C4 111.0(2) . . ? C16 C6 C7 113.90(19) . . ? C4 C6 C7 113.8(2) . . ? C16 C6 H5 105.5(15) . . ? C4 C6 H5 108.1(16) . . ? C7 C6 H5 103.8(15) . . ? C8 C7 C6 111.7(2) . . ? C8 C7 H6 114.2(17) . . ? C6 C7 H6 109.5(16) . . ? C8 C7 H7 109.6(17) . . ? C6 C7 H7 108.7(15) . . ? H6 C7 H7 103(2) . . ? C7 C8 C9 113.9(2) . . ? C7 C8 H8 112.6(17) . . ? C9 C8 H8 104.6(15) . . ? C7 C8 H9 115.6(16) . . ? C9 C8 H9 101.7(15) . . ? H8 C8 H9 107(2) . . ? O3 C9 C26 120.4(2) . . ? O3 C9 C8 120.5(3) . . ? C26 C9 C8 119.0(2) . . ? C15 C10 C11 117.5(3) . . ? C15 C10 C1 120.9(2) . . ? C11 C10 C1 121.6(2) . . ? C12 C11 C10 121.4(2) . . ? C12 C11 H10 125.5(16) . . ? C10 C11 H10 113.1(16) . . ? C11 C12 C13 119.7(2) . . ? C11 C12 H11 121.4(18) . . ? C13 C12 H11 118.9(17) . . ? C12 C13 C14 120.3(3) . . ? C12 C13 Cl1 120.1(2) . . ? C14 C13 Cl1 119.5(2) . . ? C15 C14 C13 119.5(2) . . ? C15 C14 H12 121.2(19) . . ? C13 C14 H12 119.1(19) . . ? C14 C15 C10 121.6(2) . . ? C14 C15 H13 119(2) . . ? C10 C15 H13 119.7(19) . . ? C17 C16 C24 117.8(2) . . ? C17 C16 C6 122.3(2) . . ? C24 C16 C6 119.89(19) . . ? C16 C17 C18 122.6(2) . . ? C16 C17 H14 119.4(17) . . ? C18 C17 H14 117.8(16) . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H15 119.1(17) . . ? C17 C18 H15 120.2(17) . . ? C18 C19 C25 119.5(2) . . ? C18 C19 H16 119.8(15) . . ? C25 C19 H16 120.6(15) . . ? C21 C20 C25 120.9(2) . . ? C21 C20 H17 120.9(14) . . ? C25 C20 H17 118.2(14) . . ? C20 C21 C22 119.4(2) . . ? C20 C21 H18 118.4(14) . . ? C22 C21 H18 121.9(14) . . ? C23 C22 C21 121.4(2) . . ? C23 C22 H19 117.8(17) . . ? C21 C22 H19 120.7(17) . . ? C22 C23 C24 120.6(2) . . ? C22 C23 H20 121.1(14) . . ? C24 C23 H20 118.3(14) . . ? C25 C24 C23 117.8(2) . . ? C25 C24 C16 119.6(2) . . ? C23 C24 C16 122.6(2) . . ? C24 C25 C20 119.9(2) . . ? C24 C25 C19 119.9(2) . . ? C20 C25 C19 120.2(2) . . ? C31 C26 C27 118.1(3) . . ? C31 C26 C9 118.7(2) . . ? C27 C26 C9 123.2(2) . . ? C28 C27 C26 121.4(2) . . ? C28 C27 H21 121.1(19) . . ? C26 C27 H21 117.5(19) . . ? C27 C28 C29 119.7(2) . . ? C27 C28 H22 120(2) . . ? C29 C28 H22 120(2) . . ? C30 C29 C28 120.0(3) . . ? C30 C29 Cl2 119.9(2) . . ? C28 C29 Cl2 120.0(2) . . ? C31 C30 C29 119.4(2) . . ? C31 C30 H23 120(2) . . ? C29 C30 H23 120(2) . . ? C30 C31 C26 121.3(2) . . ? C30 C31 H24 121(2) . . ? C26 C31 H24 118(2) . . ? C33 C32 C37 120.0(3) . . ? C33 C32 H25 123.0(19) . . ? C37 C32 H25 117.0(19) . . ? C32 C33 C34 120.3(3) . . ? C32 C33 H26 116(2) . . ? C34 C33 H26 123(2) . . ? C33 C34 C35 119.7(3) . . ? C33 C34 H27 124(2) . . ? C35 C34 H27 116(2) . . ? C36 C35 C34 119.8(4) . . ? C36 C35 H28 120(2) . . ? C34 C35 H28 120(2) . . ? C35 C36 C37 120.0(3) . . ? C35 C36 H29 117(2) . . ? C37 C36 H29 123(2) . . ? C36 C37 C32 120.1(3) . . ? C36 C37 H30 121.4(19) . . ? C32 C37 H30 118.5(19) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.755 _refine_diff_density_min -0.763 _refine_diff_density_rms 0.084 #============================================================================== data__3,4-Dihydro-2H-pyran-2-one/8a _database_code_depnum_ccdc_archive 'CCDC 825848' #TrackingRef '- Product 8a .cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C17 H20 O3 ' _chemical_formula_moiety 'C17 H20 O3 ' _chemical_formula_weight 272.34 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 9.3438(6) _cell_length_b 17.6011(12) _cell_length_c 10.3662(8) _cell_angle_alpha 90.0000 _cell_angle_beta 118.673(2) _cell_angle_gamma 90.0000 _cell_volume 1495.78(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9356 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 200.1 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584.00 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 14380 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _diffrn_ambient_temperature 200 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3417 _reflns_number_gt 7572 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0653 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 7572 _refine_ls_number_parameters 201 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0026Fo^2^ + 1.0000\s(Fo^2^)]' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.002 _refine_diff_density_min -0.001 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 0.96403(9) 0.16019(4) 1.23727(9) 0.0406(2) Uani 1.00 1 d . . . O(2) O 0.80948(9) 0.25649(4) 1.11513(9) 0.0441(2) Uani 1.00 1 d . . . O(3) O 0.47688(12) -0.00647(5) 0.81978(12) 0.0623(3) Uani 1.00 1 d . . . C(1) C 0.87445(13) 0.19893(6) 1.10849(12) 0.0349(2) Uani 1.00 1 d . . . C(2) C 0.85740(12) 0.16253(6) 0.96912(12) 0.0336(2) Uani 1.00 1 d . . . C(3) C 1.02465(13) 0.13245(7) 0.99691(13) 0.0398(3) Uani 1.00 1 d . . . C(4) C 1.11168(14) 0.09196(7) 1.14105(14) 0.0444(3) Uani 1.00 1 d . . . C(5) C 1.07884(14) 0.10454(6) 1.24929(14) 0.0426(3) Uani 1.00 1 d . . . C(6) C 1.15433(18) 0.06994(8) 1.39819(16) 0.0613(4) Uani 1.00 1 d . . . C(7) C 0.73721(13) 0.09534(6) 0.93362(13) 0.0360(2) Uani 1.00 1 d . . . C(8) C 0.57209(13) 0.11637(6) 0.91967(14) 0.0408(3) Uani 1.00 1 d . . . C(9) C 0.44513(14) 0.05520(7) 0.85068(13) 0.0433(3) Uani 1.00 1 d . . . C(10) C 0.27718(15) 0.07567(9) 0.82390(18) 0.0661(4) Uani 1.00 1 d . . . C(11) C 0.79238(14) 0.22272(6) 0.84480(13) 0.0365(3) Uani 1.00 1 d . . . C(12) C 0.77883(13) 0.19578(6) 0.70075(13) 0.0373(3) Uani 1.00 1 d . . . C(13) C 0.64699(14) 0.15270(7) 0.60113(13) 0.0408(3) Uani 1.00 1 d . . . C(14) C 0.63752(15) 0.12759(7) 0.47026(14) 0.0467(3) Uani 1.00 1 d . . . C(15) C 0.75814(16) 0.14592(7) 0.43514(15) 0.0499(3) Uani 1.00 1 d . . . C(16) C 0.88853(17) 0.18945(8) 0.53168(15) 0.0522(3) Uani 1.00 1 d . . . C(17) C 0.89898(15) 0.21387(7) 0.66296(14) 0.0453(3) Uani 1.00 1 d . . . H(1) H 1.0089 0.0982 0.9203 0.049 Uiso 1.00 1 c R . . H(2) H 1.0895 0.1740 0.9971 0.050 Uiso 1.00 1 c R . . H(3) H 1.1935 0.0559 1.1550 0.052 Uiso 1.00 1 c R . . H(4) H 1.2488 0.0980 1.4624 0.073 Uiso 1.00 1 c R . . H(5) H 1.1840 0.0189 1.3928 0.073 Uiso 1.00 1 c R . . H(6) H 1.0784 0.0708 1.4346 0.072 Uiso 1.00 1 c R . . H(7) H 0.7189 0.0735 0.8432 0.043 Uiso 1.00 1 c R . . H(8) H 0.7868 0.0588 1.0100 0.042 Uiso 1.00 1 c R . . H(9) H 0.5865 0.1265 1.0152 0.051 Uiso 1.00 1 c R . . H(10) H 0.5336 0.1608 0.8610 0.052 Uiso 1.00 1 c R . . H(11) H 0.2168 0.0970 0.7285 0.081 Uiso 1.00 1 c R . . H(12) H 0.2850 0.1116 0.8954 0.080 Uiso 1.00 1 c R . . H(13) H 0.2234 0.0313 0.8309 0.079 Uiso 1.00 1 c R . . H(14) H 0.6870 0.2381 0.8272 0.044 Uiso 1.00 1 c R . . H(15) H 0.8641 0.2651 0.8777 0.044 Uiso 1.00 1 c R . . H(16) H 0.5621 0.1403 0.6230 0.049 Uiso 1.00 1 c R . . H(17) H 0.5473 0.0976 0.4045 0.053 Uiso 1.00 1 c R . . H(18) H 0.7515 0.1288 0.3455 0.061 Uiso 1.00 1 c R . . H(19) H 0.9717 0.2028 0.5080 0.067 Uiso 1.00 1 c R . . H(20) H 0.9899 0.2435 0.7285 0.056 Uiso 1.00 1 c R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0437(4) 0.0419(4) 0.0372(4) 0.0048(3) 0.0201(3) -0.0004(3) O(2) 0.0506(4) 0.0380(4) 0.0474(5) 0.0067(3) 0.0265(4) -0.0065(3) O(3) 0.0641(6) 0.0552(5) 0.0648(7) -0.0195(4) 0.0288(5) -0.0197(4) C(1) 0.0357(5) 0.0348(5) 0.0367(6) -0.0033(4) 0.0194(4) -0.0017(4) C(2) 0.0361(5) 0.0322(5) 0.0354(6) 0.0022(4) 0.0194(4) -0.0030(4) C(3) 0.0388(5) 0.0407(5) 0.0437(7) 0.0018(5) 0.0227(5) -0.0051(5) C(4) 0.0403(6) 0.0396(6) 0.0498(7) 0.0068(5) 0.0187(5) -0.0044(5) C(5) 0.0436(6) 0.0349(6) 0.0429(7) 0.0036(5) 0.0156(5) -0.0008(5) C(6) 0.0698(8) 0.0537(7) 0.0509(8) 0.0083(7) 0.0213(6) 0.0087(6) C(7) 0.0421(5) 0.0316(5) 0.0341(6) -0.0001(4) 0.0182(4) -0.0016(4) C(8) 0.0445(6) 0.0383(6) 0.0443(7) -0.0038(5) 0.0251(5) -0.0032(5) C(9) 0.0438(6) 0.0509(7) 0.0328(6) -0.0063(5) 0.0164(5) 0.0029(5) C(10) 0.0433(6) 0.0822(10) 0.0692(10) -0.0071(7) 0.0240(6) 0.0135(8) C(11) 0.0409(5) 0.0321(5) 0.0378(6) 0.0000(4) 0.0199(5) -0.0020(4) C(12) 0.0428(6) 0.0351(5) 0.0351(6) 0.0043(4) 0.0196(5) 0.0040(4) C(13) 0.0406(5) 0.0427(6) 0.0391(6) 0.0019(5) 0.0192(5) 0.0021(5) C(14) 0.0484(6) 0.0481(6) 0.0367(7) 0.0036(5) 0.0149(5) -0.0027(5) C(15) 0.0613(7) 0.0556(7) 0.0368(7) 0.0101(6) 0.0268(6) 0.0019(5) C(16) 0.0585(7) 0.0612(8) 0.0480(8) 0.0011(6) 0.0345(6) 0.0049(6) C(17) 0.0464(6) 0.0486(7) 0.0438(7) -0.0027(5) 0.0239(5) 0.0027(5) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(1) 1.3694(12) yes . . O(1) C(5) 1.4133(14) yes . . O(2) C(1) 1.1999(14) yes . . O(3) C(9) 1.2083(16) yes . . C(1) C(2) 1.5173(18) yes . . C(2) C(3) 1.5406(17) yes . . C(2) C(7) 1.5487(15) yes . . C(2) C(11) 1.5495(15) yes . . C(3) C(4) 1.4952(16) yes . . C(4) C(5) 1.316(2) yes . . C(5) C(6) 1.4853(19) yes . . C(7) C(8) 1.5245(18) yes . . C(8) C(9) 1.5046(15) yes . . C(9) C(10) 1.501(2) yes . . C(11) C(12) 1.5130(19) yes . . C(12) C(13) 1.3922(14) yes . . C(12) C(17) 1.392(2) yes . . C(13) C(14) 1.389(2) yes . . C(14) C(15) 1.379(2) yes . . C(15) C(16) 1.3794(16) yes . . C(16) C(17) 1.385(2) yes . . C(3) H(1) 0.950 no . . C(3) H(2) 0.950 no . . C(4) H(3) 0.950 no . . C(6) H(4) 0.950 no . . C(6) H(5) 0.950 no . . C(6) H(6) 0.950 no . . C(7) H(7) 0.950 no . . C(7) H(8) 0.950 no . . C(8) H(9) 0.950 no . . C(8) H(10) 0.950 no . . C(10) H(11) 0.950 no . . C(10) H(12) 0.950 no . . C(10) H(13) 0.950 no . . C(11) H(14) 0.950 no . . C(11) H(15) 0.950 no . . C(13) H(16) 0.950 no . . C(14) H(17) 0.950 no . . C(15) H(18) 0.950 no . . C(16) H(19) 0.950 no . . C(17) H(20) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(1) O(1) C(5) 120.94(11) yes . . . O(1) C(1) O(2) 116.99(11) yes . . . O(1) C(1) C(2) 116.99(9) yes . . . O(2) C(1) C(2) 125.89(9) yes . . . C(1) C(2) C(3) 109.48(8) yes . . . C(1) C(2) C(7) 106.35(11) yes . . . C(1) C(2) C(11) 108.87(9) yes . . . C(3) C(2) C(7) 109.69(9) yes . . . C(3) C(2) C(11) 110.38(11) yes . . . C(7) C(2) C(11) 111.98(7) yes . . . C(2) C(3) C(4) 111.54(12) yes . . . C(3) C(4) C(5) 122.29(11) yes . . . O(1) C(5) C(4) 121.26(10) yes . . . O(1) C(5) C(6) 109.74(13) yes . . . C(4) C(5) C(6) 128.92(12) yes . . . C(2) C(7) C(8) 115.00(9) yes . . . C(7) C(8) C(9) 113.74(10) yes . . . O(3) C(9) C(8) 122.07(12) yes . . . O(3) C(9) C(10) 122.32(11) yes . . . C(8) C(9) C(10) 115.61(11) yes . . . C(2) C(11) C(12) 114.85(9) yes . . . C(11) C(12) C(13) 121.87(13) yes . . . C(11) C(12) C(17) 120.61(9) yes . . . C(13) C(12) C(17) 117.51(12) yes . . . C(12) C(13) C(14) 121.13(13) yes . . . C(13) C(14) C(15) 120.43(10) yes . . . C(14) C(15) C(16) 119.19(15) yes . . . C(15) C(16) C(17) 120.43(16) yes . . . C(12) C(17) C(16) 121.29(11) yes . . . C(2) C(3) H(1) 109.0 no . . . C(2) C(3) H(2) 109.0 no . . . C(4) C(3) H(1) 109.0 no . . . C(4) C(3) H(2) 109.0 no . . . H(1) C(3) H(2) 109.5 no . . . C(3) C(4) H(3) 118.9 no . . . C(5) C(4) H(3) 118.9 no . . . C(5) C(6) H(4) 109.5 no . . . C(5) C(6) H(5) 109.5 no . . . C(5) C(6) H(6) 109.5 no . . . H(4) C(6) H(5) 109.5 no . . . H(4) C(6) H(6) 109.5 no . . . H(5) C(6) H(6) 109.5 no . . . C(2) C(7) H(7) 108.1 no . . . C(2) C(7) H(8) 108.1 no . . . C(8) C(7) H(7) 108.1 no . . . C(8) C(7) H(8) 108.1 no . . . H(7) C(7) H(8) 109.5 no . . . C(7) C(8) H(9) 108.4 no . . . C(7) C(8) H(10) 108.4 no . . . C(9) C(8) H(9) 108.4 no . . . C(9) C(8) H(10) 108.4 no . . . H(9) C(8) H(10) 109.5 no . . . C(9) C(10) H(11) 109.5 no . . . C(9) C(10) H(12) 109.5 no . . . C(9) C(10) H(13) 109.5 no . . . H(11) C(10) H(12) 109.5 no . . . H(11) C(10) H(13) 109.5 no . . . H(12) C(10) H(13) 109.5 no . . . C(2) C(11) H(14) 108.1 no . . . C(2) C(11) H(15) 108.1 no . . . C(12) C(11) H(14) 108.1 no . . . C(12) C(11) H(15) 108.1 no . . . H(14) C(11) H(15) 109.5 no . . . C(12) C(13) H(16) 119.4 no . . . C(14) C(13) H(16) 119.4 no . . . C(13) C(14) H(17) 119.8 no . . . C(15) C(14) H(17) 119.8 no . . . C(14) C(15) H(18) 120.4 no . . . C(16) C(15) H(18) 120.4 no . . . C(15) C(16) H(19) 119.8 no . . . C(17) C(16) H(19) 119.8 no . . . C(12) C(17) H(20) 119.4 no . . . C(16) C(17) H(20) 119.4 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(1) O(1) C(5) C(4) 4.86(15) ? . . . . C(1) O(1) C(5) C(6) -178.21(9) ? . . . . C(5) O(1) C(1) O(2) -162.84(10) ? . . . . C(5) O(1) C(1) C(2) 21.02(14) ? . . . . O(1) C(1) C(2) C(3) -44.87(14) ? . . . . O(1) C(1) C(2) C(7) 73.56(11) ? . . . . O(1) C(1) C(2) C(11) -165.61(9) ? . . . . O(2) C(1) C(2) C(3) 139.38(12) ? . . . . O(2) C(1) C(2) C(7) -102.19(13) ? . . . . O(2) C(1) C(2) C(11) 18.63(16) ? . . . . C(1) C(2) C(3) C(4) 43.99(12) ? . . . . C(1) C(2) C(7) C(8) 55.54(11) ? . . . . C(1) C(2) C(11) C(12) 176.44(9) ? . . . . C(3) C(2) C(7) C(8) 173.84(10) ? . . . . C(7) C(2) C(3) C(4) -72.35(12) ? . . . . C(3) C(2) C(11) C(12) 56.26(11) ? . . . . C(11) C(2) C(3) C(4) 163.81(9) ? . . . . C(7) C(2) C(11) C(12) -66.25(14) ? . . . . C(11) C(2) C(7) C(8) -63.26(15) ? . . . . C(2) C(3) C(4) C(5) -22.78(15) ? . . . . C(3) C(4) C(5) O(1) -3.13(17) ? . . . . C(3) C(4) C(5) C(6) -179.42(11) ? . . . . C(2) C(7) C(8) C(9) 166.20(10) ? . . . . C(7) C(8) C(9) O(3) 5.01(19) ? . . . . C(7) C(8) C(9) C(10) -175.41(12) ? . . . . C(2) C(11) C(12) C(13) 80.81(13) ? . . . . C(2) C(11) C(12) C(17) -99.52(12) ? . . . . C(11) C(12) C(13) C(14) -179.15(10) ? . . . . C(11) C(12) C(17) C(16) 179.82(10) ? . . . . C(13) C(12) C(17) C(16) -0.49(16) ? . . . . C(17) C(12) C(13) C(14) 1.17(16) ? . . . . C(12) C(13) C(14) C(15) -0.98(17) ? . . . . C(13) C(14) C(15) C(16) 0.08(16) ? . . . . C(14) C(15) C(16) C(17) 0.60(18) ? . . . . C(15) C(16) C(17) C(12) -0.39(18) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) O(2) 2.1925(9) ? . . O(1) C(2) 2.4624(14) ? . . O(1) C(3) 2.8499(18) ? . . O(1) C(4) 2.3793(18) ? . . O(1) C(6) 2.3709(14) ? . . O(1) C(7) 3.0497(12) ? . . O(1) C(11) 3.4089(13) ? . 4_555 O(1) C(15) 3.429(2) ? . 1_556 O(1) C(16) 3.485(2) ? . 1_556 O(2) O(1) 2.1925(9) ? . . O(2) C(2) 2.4242(15) ? . . O(2) C(3) 3.5602(17) ? . . O(2) C(5) 3.4731(12) ? . . O(2) C(7) 3.2897(13) ? . . O(2) C(8) 3.2856(12) ? . . O(2) C(11) 2.7932(17) ? . . O(3) O(3) 3.5567(18) ? . 3_657 O(3) C(7) 2.7868(14) ? . . O(3) C(8) 2.3779(13) ? . . O(3) C(8) 3.5259(19) ? . 3_657 O(3) C(9) 3.2477(18) ? . 3_657 O(3) C(10) 2.377(2) ? . . O(3) C(10) 3.5018(17) ? . 3_657 O(3) C(14) 3.4122(16) ? . 3_656 O(3) C(15) 3.5016(14) ? . 3_656 C(1) C(3) 2.497(2) ? . . C(1) C(4) 2.8026(17) ? . . C(1) C(5) 2.4213(14) ? . . C(1) C(7) 2.4544(14) ? . . C(1) C(8) 2.9356(13) ? . . C(1) C(11) 2.4947(18) ? . . C(2) O(1) 2.4624(14) ? . . C(2) O(2) 2.4242(15) ? . . C(2) C(4) 2.5101(14) ? . . C(2) C(5) 2.8269(14) ? . . C(2) C(8) 2.5920(17) ? . . C(2) C(12) 2.5809(18) ? . . C(2) C(13) 3.3541(15) ? . . C(2) C(17) 3.496(2) ? . . C(3) O(1) 2.8499(18) ? . . C(3) O(2) 3.5602(17) ? . . C(3) C(1) 2.497(2) ? . . C(3) C(5) 2.464(2) ? . . C(3) C(7) 2.5258(17) ? . . C(3) C(11) 2.5371(14) ? . . C(3) C(12) 3.0293(14) ? . . C(3) C(17) 3.3935(18) ? . . C(4) O(1) 2.3793(18) ? . . C(4) C(1) 2.8026(17) ? . . C(4) C(2) 2.5101(14) ? . . C(4) C(6) 2.529(2) ? . . C(4) C(7) 3.1065(14) ? . . C(5) O(2) 3.4731(12) ? . . C(5) C(1) 2.4213(14) ? . . C(5) C(2) 2.8269(14) ? . . C(5) C(3) 2.464(2) ? . . C(5) C(7) 3.3015(13) ? . . C(5) C(11) 3.5085(15) ? . 4_555 C(6) O(1) 2.3709(14) ? . . C(6) C(4) 2.529(2) ? . . C(7) O(1) 3.0497(12) ? . . C(7) O(2) 3.2897(13) ? . . C(7) O(3) 2.7868(14) ? . . C(7) C(1) 2.4544(14) ? . . C(7) C(3) 2.5258(17) ? . . C(7) C(4) 3.1065(14) ? . . C(7) C(5) 3.3015(13) ? . . C(7) C(9) 2.5367(17) ? . . C(7) C(11) 2.5682(17) ? . . C(7) C(12) 3.1630(19) ? . . C(7) C(13) 3.2896(18) ? . . C(8) O(2) 3.2856(12) ? . . C(8) O(3) 2.3779(13) ? . . C(8) O(3) 3.5259(19) ? . 3_657 C(8) C(1) 2.9356(13) ? . . C(8) C(2) 2.5920(17) ? . . C(8) C(10) 2.5430(17) ? . . C(8) C(11) 3.1426(19) ? . . C(9) O(3) 3.2477(18) ? . 3_657 C(9) C(7) 2.5367(17) ? . . C(9) C(9) 3.3712(18) ? . 3_657 C(10) O(3) 2.377(2) ? . . C(10) O(3) 3.5018(17) ? . 3_657 C(10) C(8) 2.5430(17) ? . . C(11) O(1) 3.4089(13) ? . 4_454 C(11) O(2) 2.7932(17) ? . . C(11) C(1) 2.4947(18) ? . . C(11) C(3) 2.5371(14) ? . . C(11) C(5) 3.5085(15) ? . 4_454 C(11) C(7) 2.5682(17) ? . . C(11) C(8) 3.1426(19) ? . . C(11) C(13) 2.5400(16) ? . . C(11) C(17) 2.524(2) ? . . C(12) C(2) 2.5809(18) ? . . C(12) C(3) 3.0293(14) ? . . C(12) C(7) 3.1630(19) ? . . C(12) C(14) 2.4218(16) ? . . C(12) C(15) 2.807(2) ? . . C(12) C(16) 2.420(2) ? . . C(13) C(2) 3.3541(15) ? . . C(13) C(7) 3.2896(18) ? . . C(13) C(11) 2.5400(16) ? . . C(13) C(15) 2.402(2) ? . . C(13) C(16) 2.755(2) ? . . C(13) C(17) 2.3803(18) ? . . C(14) O(3) 3.4122(16) ? . 3_656 C(14) C(12) 2.4218(16) ? . . C(14) C(16) 2.379(2) ? . . C(14) C(17) 2.7535(15) ? . . C(15) O(1) 3.429(2) ? . 1_554 C(15) O(3) 3.5016(14) ? . 3_656 C(15) C(12) 2.807(2) ? . . C(15) C(13) 2.402(2) ? . . C(15) C(17) 2.3994(17) ? . . C(16) O(1) 3.485(2) ? . 1_554 C(16) C(12) 2.420(2) ? . . C(16) C(13) 2.755(2) ? . . C(16) C(14) 2.379(2) ? . . C(17) C(2) 3.496(2) ? . . C(17) C(3) 3.3935(18) ? . . C(17) C(11) 2.524(2) ? . . C(17) C(13) 2.3803(18) ? . . C(17) C(14) 2.7535(15) ? . . C(17) C(15) 2.3994(17) ? . . O(1) H(2) 3.231 ? . . O(1) H(3) 3.233 ? . . O(1) H(4) 2.787 ? . . O(1) H(5) 3.135 ? . . O(1) H(6) 2.388 ? . . O(1) H(8) 2.781 ? . . O(1) H(9) 3.209 ? . . O(1) H(10) 3.345 ? . 4_555 O(1) H(14) 2.560 ? . 4_555 O(1) H(15) 3.550 ? . 4_555 O(1) H(18) 2.765 ? . 1_556 O(1) H(19) 2.872 ? . 1_556 O(2) H(4) 2.920 ? . 4_454 O(2) H(9) 2.928 ? . . O(2) H(10) 3.147 ? . . O(2) H(10) 2.806 ? . 4_555 O(2) H(11) 3.123 ? . 4_555 O(2) H(14) 2.655 ? . . O(2) H(14) 3.138 ? . 4_555 O(2) H(15) 2.747 ? . . O(2) H(16) 2.948 ? . 4_555 O(2) H(18) 3.506 ? . 1_556 O(2) H(19) 2.889 ? . 4_455 O(3) H(3) 3.088 ? . 3_757 O(3) H(7) 2.575 ? . . O(3) H(8) 2.849 ? . . O(3) H(9) 2.940 ? . . O(3) H(9) 2.952 ? . 3_657 O(3) H(10) 2.987 ? . . O(3) H(11) 2.813 ? . . O(3) H(12) 3.082 ? . . O(3) H(12) 3.285 ? . 3_657 O(3) H(13) 2.516 ? . . O(3) H(13) 3.379 ? . 3_657 O(3) H(17) 2.743 ? . 3_656 O(3) H(18) 2.936 ? . 3_656 C(1) H(1) 3.298 ? . . C(1) H(2) 2.792 ? . . C(1) H(7) 3.274 ? . . C(1) H(8) 2.644 ? . . C(1) H(9) 2.702 ? . . C(1) H(10) 3.055 ? . . C(1) H(10) 3.379 ? . 4_555 C(1) H(14) 2.673 ? . . C(1) H(14) 2.923 ? . 4_555 C(1) H(15) 2.621 ? . . C(1) H(16) 3.294 ? . 4_555 C(1) H(18) 3.404 ? . 1_556 C(2) H(1) 2.056 ? . . C(2) H(2) 2.056 ? . . C(2) H(3) 3.360 ? . . C(2) H(7) 2.053 ? . . C(2) H(8) 2.053 ? . . C(2) H(9) 2.863 ? . . C(2) H(10) 2.675 ? . . C(2) H(14) 2.054 ? . . C(2) H(15) 2.054 ? . . C(2) H(16) 3.337 ? . . C(2) H(20) 3.571 ? . . C(3) H(3) 2.124 ? . . C(3) H(7) 2.722 ? . . C(3) H(8) 2.632 ? . . C(3) H(12) 3.101 ? . 1_655 C(3) H(13) 3.556 ? . 1_655 C(3) H(14) 3.343 ? . . C(3) H(15) 2.729 ? . . C(3) H(20) 3.287 ? . . C(4) H(1) 2.015 ? . . C(4) H(1) 3.492 ? . 3_757 C(4) H(2) 2.015 ? . . C(4) H(4) 2.942 ? . . C(4) H(5) 2.689 ? . . C(4) H(6) 3.225 ? . . C(4) H(7) 3.498 ? . . C(4) H(7) 3.281 ? . 3_757 C(4) H(8) 2.728 ? . . C(4) H(8) 3.438 ? . 3_757 C(4) H(14) 3.445 ? . 4_555 C(4) H(15) 3.515 ? . 4_555 C(5) H(1) 3.151 ? . . C(5) H(2) 2.931 ? . . C(5) H(3) 1.960 ? . . C(5) H(4) 2.012 ? . . C(5) H(5) 2.012 ? . . C(5) H(6) 2.012 ? . . C(5) H(8) 2.784 ? . . C(5) H(13) 3.483 ? . 3_657 C(5) H(14) 2.927 ? . 4_555 C(5) H(15) 3.277 ? . 4_555 C(6) H(3) 2.727 ? . . C(6) H(11) 3.221 ? . 1_656 C(6) H(14) 3.503 ? . 4_555 C(6) H(15) 3.566 ? . 4_555 C(6) H(16) 3.600 ? . 1_656 C(6) H(19) 3.396 ? . 1_556 C(7) H(1) 2.608 ? . . C(7) H(2) 3.333 ? . . C(7) H(3) 2.987 ? . 3_757 C(7) H(9) 2.035 ? . . C(7) H(10) 2.035 ? . . C(7) H(13) 3.194 ? . 3_657 C(7) H(14) 2.693 ? . . C(7) H(15) 3.366 ? . . C(7) H(16) 2.935 ? . . C(8) H(7) 2.031 ? . . C(8) H(8) 2.031 ? . . C(8) H(11) 2.958 ? . . C(8) H(12) 2.572 ? . . C(8) H(13) 3.291 ? . . C(8) H(13) 3.515 ? . 3_657 C(8) H(14) 2.766 ? . . C(8) H(16) 3.060 ? . . C(8) H(19) 3.561 ? . 4_455 C(9) H(7) 2.616 ? . . C(9) H(8) 2.804 ? . . C(9) H(9) 2.017 ? . . C(9) H(9) 3.556 ? . 3_657 C(9) H(10) 2.017 ? . . C(9) H(11) 2.026 ? . . C(9) H(12) 2.026 ? . . C(9) H(13) 2.026 ? . . C(9) H(16) 3.388 ? . . C(10) H(1) 3.138 ? . 1_455 C(10) H(2) 3.509 ? . 1_455 C(10) H(6) 3.543 ? . 1_454 C(10) H(8) 3.149 ? . 3_657 C(10) H(9) 2.755 ? . . C(10) H(10) 2.693 ? . . C(11) H(1) 2.826 ? . . C(11) H(2) 2.594 ? . . C(11) H(4) 3.476 ? . 4_454 C(11) H(7) 2.713 ? . . C(11) H(8) 3.368 ? . . C(11) H(9) 3.598 ? . . C(11) H(10) 2.729 ? . . C(11) H(16) 2.697 ? . . C(11) H(20) 2.670 ? . . C(12) H(1) 2.838 ? . . C(12) H(2) 3.075 ? . . C(12) H(2) 3.042 ? . 4_454 C(12) H(7) 2.814 ? . . C(12) H(10) 3.470 ? . . C(12) H(14) 2.021 ? . . C(12) H(15) 2.021 ? . . C(12) H(16) 2.035 ? . . C(12) H(17) 3.275 ? . . C(12) H(19) 3.273 ? . . C(12) H(20) 2.034 ? . . C(13) H(1) 3.545 ? . . C(13) H(2) 3.193 ? . 4_454 C(13) H(4) 3.421 ? . 1_454 C(13) H(5) 3.394 ? . 3_757 C(13) H(7) 2.660 ? . . C(13) H(10) 3.337 ? . . C(13) H(14) 2.655 ? . . C(13) H(15) 3.266 ? . . C(13) H(15) 2.927 ? . 4_454 C(13) H(17) 2.035 ? . . C(13) H(18) 3.261 ? . . C(13) H(20) 3.242 ? . . C(14) H(2) 3.548 ? . 4_454 C(14) H(5) 3.028 ? . 3_757 C(14) H(15) 2.943 ? . 4_454 C(14) H(16) 2.032 ? . . C(14) H(18) 2.032 ? . . C(14) H(19) 3.238 ? . . C(14) H(20) 3.164 ? . 4_454 C(15) H(5) 3.311 ? . 3_757 C(15) H(6) 3.274 ? . 1_554 C(15) H(16) 3.254 ? . . C(15) H(17) 2.026 ? . . C(15) H(19) 2.027 ? . . C(15) H(20) 3.251 ? . . C(15) H(20) 3.083 ? . 4_454 C(16) H(2) 3.570 ? . 4_454 C(16) H(6) 3.199 ? . 1_554 C(16) H(11) 3.196 ? . 1_655 C(16) H(17) 3.238 ? . . C(16) H(18) 2.033 ? . . C(16) H(20) 2.028 ? . . C(17) H(1) 3.112 ? . . C(17) H(2) 3.121 ? . . C(17) H(2) 3.231 ? . 4_454 C(17) H(11) 3.402 ? . 1_655 C(17) H(14) 3.199 ? . . C(17) H(15) 2.563 ? . . C(17) H(16) 3.242 ? . . C(17) H(18) 3.258 ? . . C(17) H(19) 2.032 ? . . H(1) C(1) 3.298 ? . . H(1) C(2) 2.056 ? . . H(1) C(4) 2.015 ? . . H(1) C(4) 3.492 ? . 3_757 H(1) C(5) 3.151 ? . . H(1) C(7) 2.608 ? . . H(1) C(10) 3.138 ? . 1_655 H(1) C(11) 2.826 ? . . H(1) C(12) 2.838 ? . . H(1) C(13) 3.545 ? . . H(1) C(17) 3.112 ? . . H(1) H(2) 1.551 ? . . H(1) H(3) 2.329 ? . . H(1) H(3) 3.183 ? . 3_757 H(1) H(5) 3.524 ? . 3_757 H(1) H(7) 2.468 ? . . H(1) H(8) 2.739 ? . . H(1) H(8) 3.238 ? . 3_757 H(1) H(11) 3.382 ? . 1_655 H(1) H(12) 2.724 ? . 1_655 H(1) H(13) 2.837 ? . 1_655 H(1) H(15) 3.175 ? . . H(1) H(20) 3.192 ? . . H(2) O(1) 3.231 ? . . H(2) C(1) 2.792 ? . . H(2) C(2) 2.056 ? . . H(2) C(4) 2.015 ? . . H(2) C(5) 2.931 ? . . H(2) C(7) 3.333 ? . . H(2) C(10) 3.509 ? . 1_655 H(2) C(11) 2.594 ? . . H(2) C(12) 3.075 ? . . H(2) C(12) 3.042 ? . 4_555 H(2) C(13) 3.193 ? . 4_555 H(2) C(14) 3.548 ? . 4_555 H(2) C(16) 3.570 ? . 4_555 H(2) C(17) 3.121 ? . . H(2) C(17) 3.231 ? . 4_555 H(2) H(1) 1.551 ? . . H(2) H(3) 2.534 ? . . H(2) H(7) 3.517 ? . . H(2) H(8) 3.535 ? . . H(2) H(12) 2.739 ? . 1_655 H(2) H(13) 3.593 ? . 1_655 H(2) H(14) 3.487 ? . . H(2) H(14) 3.456 ? . 4_555 H(2) H(15) 2.457 ? . . H(2) H(16) 3.574 ? . 4_555 H(2) H(20) 2.762 ? . . H(3) O(1) 3.233 ? . . H(3) O(3) 3.088 ? . 3_757 H(3) C(2) 3.360 ? . . H(3) C(3) 2.124 ? . . H(3) C(5) 1.960 ? . . H(3) C(6) 2.727 ? . . H(3) C(7) 2.987 ? . 3_757 H(3) H(1) 2.329 ? . . H(3) H(1) 3.183 ? . 3_757 H(3) H(2) 2.534 ? . . H(3) H(4) 3.064 ? . . H(3) H(5) 2.592 ? . . H(3) H(6) 3.552 ? . . H(3) H(7) 2.417 ? . 3_757 H(3) H(8) 3.350 ? . . H(3) H(8) 2.709 ? . 3_757 H(3) H(12) 3.338 ? . 1_655 H(3) H(13) 3.529 ? . 1_655 H(3) H(17) 3.155 ? . 1_656 H(4) O(1) 2.787 ? . . H(4) O(2) 2.920 ? . 4_555 H(4) C(4) 2.942 ? . . H(4) C(5) 2.012 ? . . H(4) C(11) 3.476 ? . 4_555 H(4) C(13) 3.421 ? . 1_656 H(4) H(3) 3.064 ? . . H(4) H(5) 1.551 ? . . H(4) H(6) 1.551 ? . . H(4) H(11) 2.914 ? . 1_656 H(4) H(14) 3.138 ? . 4_555 H(4) H(15) 2.940 ? . 4_555 H(4) H(16) 2.686 ? . 1_656 H(4) H(17) 3.122 ? . 1_656 H(4) H(19) 3.391 ? . 1_556 H(5) O(1) 3.135 ? . . H(5) C(4) 2.689 ? . . H(5) C(5) 2.012 ? . . H(5) C(13) 3.394 ? . 3_757 H(5) C(14) 3.028 ? . 3_757 H(5) C(15) 3.311 ? . 3_757 H(5) H(1) 3.524 ? . 3_757 H(5) H(3) 2.592 ? . . H(5) H(4) 1.551 ? . . H(5) H(6) 1.551 ? . . H(5) H(7) 3.403 ? . 3_757 H(5) H(13) 3.490 ? . 3_657 H(5) H(17) 3.139 ? . 3_757 H(5) H(18) 3.593 ? . 3_757 H(6) O(1) 2.388 ? . . H(6) C(4) 3.225 ? . . H(6) C(5) 2.012 ? . . H(6) C(10) 3.543 ? . 1_656 H(6) C(15) 3.274 ? . 1_556 H(6) C(16) 3.199 ? . 1_556 H(6) H(3) 3.552 ? . . H(6) H(4) 1.551 ? . . H(6) H(5) 1.551 ? . . H(6) H(6) 3.480 ? . 3_758 H(6) H(11) 2.718 ? . 1_656 H(6) H(13) 3.363 ? . 3_657 H(6) H(18) 2.918 ? . 1_556 H(6) H(19) 2.774 ? . 1_556 H(7) O(3) 2.575 ? . . H(7) C(1) 3.274 ? . . H(7) C(2) 2.053 ? . . H(7) C(3) 2.722 ? . . H(7) C(4) 3.498 ? . . H(7) C(4) 3.281 ? . 3_757 H(7) C(8) 2.031 ? . . H(7) C(9) 2.616 ? . . H(7) C(11) 2.713 ? . . H(7) C(12) 2.814 ? . . H(7) C(13) 2.660 ? . . H(7) H(1) 2.468 ? . . H(7) H(2) 3.517 ? . . H(7) H(3) 2.417 ? . 3_757 H(7) H(5) 3.403 ? . 3_757 H(7) H(8) 1.551 ? . . H(7) H(9) 2.775 ? . . H(7) H(10) 2.388 ? . . H(7) H(14) 2.909 ? . . H(7) H(15) 3.588 ? . . H(7) H(16) 2.351 ? . . H(8) O(1) 2.781 ? . . H(8) O(3) 2.849 ? . . H(8) C(1) 2.644 ? . . H(8) C(2) 2.053 ? . . H(8) C(3) 2.632 ? . . H(8) C(4) 2.728 ? . . H(8) C(4) 3.438 ? . 3_757 H(8) C(5) 2.784 ? . . H(8) C(8) 2.031 ? . . H(8) C(9) 2.804 ? . . H(8) C(10) 3.149 ? . 3_657 H(8) C(11) 3.368 ? . . H(8) H(1) 2.739 ? . . H(8) H(1) 3.238 ? . 3_757 H(8) H(2) 3.535 ? . . H(8) H(3) 3.350 ? . . H(8) H(3) 2.709 ? . 3_757 H(8) H(7) 1.551 ? . . H(8) H(9) 2.241 ? . . H(8) H(10) 2.775 ? . . H(8) H(12) 3.323 ? . 3_657 H(8) H(13) 2.323 ? . 3_657 H(8) H(14) 3.566 ? . . H(9) O(1) 3.209 ? . . H(9) O(2) 2.928 ? . . H(9) O(3) 2.940 ? . . H(9) O(3) 2.952 ? . 3_657 H(9) C(1) 2.702 ? . . H(9) C(2) 2.863 ? . . H(9) C(7) 2.035 ? . . H(9) C(9) 2.017 ? . . H(9) C(9) 3.556 ? . 3_657 H(9) C(10) 2.755 ? . . H(9) C(11) 3.598 ? . . H(9) H(7) 2.775 ? . . H(9) H(8) 2.241 ? . . H(9) H(10) 1.551 ? . . H(9) H(11) 3.344 ? . . H(9) H(12) 2.488 ? . . H(9) H(13) 3.428 ? . . H(9) H(13) 3.271 ? . 3_657 H(9) H(14) 3.208 ? . . H(9) H(18) 3.006 ? . 1_556 H(9) H(19) 3.179 ? . 4_455 H(9) H(20) 3.584 ? . 4_455 H(10) O(1) 3.345 ? . 4_454 H(10) O(2) 3.147 ? . . H(10) O(2) 2.806 ? . 4_454 H(10) O(3) 2.987 ? . . H(10) C(1) 3.055 ? . . H(10) C(1) 3.379 ? . 4_454 H(10) C(2) 2.675 ? . . H(10) C(7) 2.035 ? . . H(10) C(9) 2.017 ? . . H(10) C(10) 2.693 ? . . H(10) C(11) 2.729 ? . . H(10) C(12) 3.470 ? . . H(10) C(13) 3.337 ? . . H(10) H(7) 2.388 ? . . H(10) H(8) 2.775 ? . . H(10) H(9) 1.551 ? . . H(10) H(11) 2.830 ? . . H(10) H(12) 2.659 ? . . H(10) H(13) 3.582 ? . . H(10) H(14) 2.123 ? . . H(10) H(15) 3.524 ? . . H(10) H(16) 2.629 ? . . H(10) H(19) 3.044 ? . 4_455 H(11) O(2) 3.123 ? . 4_454 H(11) O(3) 2.813 ? . . H(11) C(6) 3.221 ? . 1_454 H(11) C(8) 2.958 ? . . H(11) C(9) 2.026 ? . . H(11) C(16) 3.196 ? . 1_455 H(11) C(17) 3.402 ? . 1_455 H(11) H(1) 3.382 ? . 1_455 H(11) H(4) 2.914 ? . 1_454 H(11) H(6) 2.718 ? . 1_454 H(11) H(9) 3.344 ? . . H(11) H(10) 2.830 ? . . H(11) H(12) 1.551 ? . . H(11) H(13) 1.551 ? . . H(11) H(19) 2.985 ? . 1_455 H(11) H(20) 3.338 ? . 1_455 H(12) O(3) 3.082 ? . . H(12) O(3) 3.285 ? . 3_657 H(12) C(3) 3.101 ? . 1_455 H(12) C(8) 2.572 ? . . H(12) C(9) 2.026 ? . . H(12) H(1) 2.724 ? . 1_455 H(12) H(2) 2.739 ? . 1_455 H(12) H(3) 3.338 ? . 1_455 H(12) H(8) 3.323 ? . 3_657 H(12) H(9) 2.488 ? . . H(12) H(10) 2.659 ? . . H(12) H(11) 1.551 ? . . H(12) H(13) 1.551 ? . . H(12) H(20) 3.378 ? . 1_455 H(13) O(3) 2.516 ? . . H(13) O(3) 3.379 ? . 3_657 H(13) C(3) 3.556 ? . 1_455 H(13) C(5) 3.483 ? . 3_657 H(13) C(7) 3.194 ? . 3_657 H(13) C(8) 3.291 ? . . H(13) C(8) 3.515 ? . 3_657 H(13) C(9) 2.026 ? . . H(13) H(1) 2.837 ? . 1_455 H(13) H(2) 3.593 ? . 1_455 H(13) H(3) 3.529 ? . 1_455 H(13) H(5) 3.490 ? . 3_657 H(13) H(6) 3.363 ? . 3_657 H(13) H(8) 2.323 ? . 3_657 H(13) H(9) 3.428 ? . . H(13) H(9) 3.271 ? . 3_657 H(13) H(10) 3.582 ? . . H(13) H(11) 1.551 ? . . H(13) H(12) 1.551 ? . . H(13) H(18) 3.428 ? . 3_656 H(14) O(1) 2.560 ? . 4_454 H(14) O(2) 2.655 ? . . H(14) O(2) 3.138 ? . 4_454 H(14) C(1) 2.673 ? . . H(14) C(1) 2.923 ? . 4_454 H(14) C(2) 2.054 ? . . H(14) C(3) 3.343 ? . . H(14) C(4) 3.445 ? . 4_454 H(14) C(5) 2.927 ? . 4_454 H(14) C(6) 3.503 ? . 4_454 H(14) C(7) 2.693 ? . . H(14) C(8) 2.766 ? . . H(14) C(12) 2.021 ? . . H(14) C(13) 2.655 ? . . H(14) C(17) 3.199 ? . . H(14) H(2) 3.487 ? . . H(14) H(2) 3.456 ? . 4_454 H(14) H(4) 3.138 ? . 4_454 H(14) H(7) 2.909 ? . . H(14) H(8) 3.566 ? . . H(14) H(9) 3.208 ? . . H(14) H(10) 2.123 ? . . H(14) H(15) 1.551 ? . . H(14) H(16) 2.536 ? . . H(14) H(19) 3.502 ? . 4_455 H(14) H(20) 3.442 ? . . H(15) O(1) 3.550 ? . 4_454 H(15) O(2) 2.747 ? . . H(15) C(1) 2.621 ? . . H(15) C(2) 2.054 ? . . H(15) C(3) 2.729 ? . . H(15) C(4) 3.515 ? . 4_454 H(15) C(5) 3.277 ? . 4_454 H(15) C(6) 3.566 ? . 4_454 H(15) C(7) 3.366 ? . . H(15) C(12) 2.021 ? . . H(15) C(13) 3.266 ? . . H(15) C(13) 2.927 ? . 4_555 H(15) C(14) 2.943 ? . 4_555 H(15) C(17) 2.563 ? . . H(15) H(1) 3.175 ? . . H(15) H(2) 2.457 ? . . H(15) H(4) 2.940 ? . 4_454 H(15) H(7) 3.588 ? . . H(15) H(10) 3.524 ? . . H(15) H(14) 1.551 ? . . H(15) H(16) 3.551 ? . . H(15) H(16) 2.855 ? . 4_555 H(15) H(17) 2.897 ? . 4_555 H(15) H(20) 2.380 ? . . H(16) O(2) 2.948 ? . 4_454 H(16) C(1) 3.294 ? . 4_454 H(16) C(2) 3.337 ? . . H(16) C(6) 3.600 ? . 1_454 H(16) C(7) 2.935 ? . . H(16) C(8) 3.060 ? . . H(16) C(9) 3.388 ? . . H(16) C(11) 2.697 ? . . H(16) C(12) 2.035 ? . . H(16) C(14) 2.032 ? . . H(16) C(15) 3.254 ? . . H(16) C(17) 3.242 ? . . H(16) H(2) 3.574 ? . 4_454 H(16) H(4) 2.686 ? . 1_454 H(16) H(7) 2.351 ? . . H(16) H(10) 2.629 ? . . H(16) H(14) 2.536 ? . . H(16) H(15) 3.551 ? . . H(16) H(15) 2.855 ? . 4_454 H(16) H(17) 2.327 ? . . H(17) O(3) 2.743 ? . 3_656 H(17) C(12) 3.275 ? . . H(17) C(13) 2.035 ? . . H(17) C(15) 2.026 ? . . H(17) C(16) 3.238 ? . . H(17) H(3) 3.155 ? . 1_454 H(17) H(4) 3.122 ? . 1_454 H(17) H(5) 3.139 ? . 3_757 H(17) H(15) 2.897 ? . 4_454 H(17) H(16) 2.327 ? . . H(17) H(18) 2.331 ? . . H(17) H(20) 3.240 ? . 4_454 H(18) O(1) 2.765 ? . 1_554 H(18) O(2) 3.506 ? . 1_554 H(18) O(3) 2.936 ? . 3_656 H(18) C(1) 3.404 ? . 1_554 H(18) C(13) 3.261 ? . . H(18) C(14) 2.032 ? . . H(18) C(16) 2.033 ? . . H(18) C(17) 3.258 ? . . H(18) H(5) 3.593 ? . 3_757 H(18) H(6) 2.918 ? . 1_554 H(18) H(9) 3.006 ? . 1_554 H(18) H(13) 3.428 ? . 3_656 H(18) H(17) 2.331 ? . . H(18) H(19) 2.332 ? . . H(18) H(20) 3.107 ? . 4_454 H(19) O(1) 2.872 ? . 1_554 H(19) O(2) 2.889 ? . 4_554 H(19) C(6) 3.396 ? . 1_554 H(19) C(8) 3.561 ? . 4_554 H(19) C(12) 3.273 ? . . H(19) C(14) 3.238 ? . . H(19) C(15) 2.027 ? . . H(19) C(17) 2.032 ? . . H(19) H(4) 3.391 ? . 1_554 H(19) H(6) 2.774 ? . 1_554 H(19) H(9) 3.179 ? . 4_554 H(19) H(10) 3.044 ? . 4_554 H(19) H(11) 2.985 ? . 1_655 H(19) H(14) 3.502 ? . 4_554 H(19) H(18) 2.332 ? . . H(19) H(20) 2.323 ? . . H(20) C(2) 3.571 ? . . H(20) C(3) 3.287 ? . . H(20) C(11) 2.670 ? . . H(20) C(12) 2.034 ? . . H(20) C(13) 3.242 ? . . H(20) C(14) 3.164 ? . 4_555 H(20) C(15) 3.251 ? . . H(20) C(15) 3.083 ? . 4_555 H(20) C(16) 2.028 ? . . H(20) H(1) 3.192 ? . . H(20) H(2) 2.762 ? . . H(20) H(9) 3.584 ? . 4_554 H(20) H(11) 3.338 ? . 1_655 H(20) H(12) 3.378 ? . 1_655 H(20) H(14) 3.442 ? . . H(20) H(15) 2.380 ? . . H(20) H(17) 3.240 ? . 4_555 H(20) H(18) 3.107 ? . 4_555 H(20) H(19) 2.323 ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================