# ja020615r.cif data_1 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H22 O6 ' _chemical_formula_moiety 'C22 H22 O6 ' _chemical_formula_weight 382.41 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' 'x+1/2,y+1/2,z' '-x+1/2,-y+1/2,-z' '-x,y,-z+1/2' 'x,-y,z+1/2' '-x+1/2,y+1/2,-z+1/2' 'x+1/2,-y+1/2,z+1/2' #------------------------------------------------------------------------------ _cell_length_a 36.026(3) _cell_length_b 5.6019(4) _cell_length_c 9.4840(7) _cell_angle_alpha 90 _cell_angle_beta 100.27(1) _cell_angle_gamma 90 _cell_volume 1883.4(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6583 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 203.1 #------------------------------------------------------------------------------ _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 7901 _diffrn_reflns_av_R_equivalents 0.087 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9904 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.9904 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 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 2367 _reflns_number_gt 1252 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.1040 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1269 _refine_ls_number_parameters 171 _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.005Fo^2^ + 1.000\s^2^(Fo)]' _refine_ls_shift/su_max 0.0020 _refine_diff_density_max 0.31 _refine_diff_density_min -0.25 _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' 0.006 0.003 ; 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' 0.017 0.010 ; 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 O1 O 0.0418(1) 0.1200(6) 0.1594(5) 0.093(1) Uani 1.00 1 d . . . O2 O 0.07830(7) 0.3294(5) 0.3249(3) 0.0428(8) Uani 1.00 1 d . . . O3 O 0.21650(7) 0.2905(5) 0.8345(3) 0.0433(8) Uani 1.00 1 d . . . C1 C 0.0512(1) 0.3089(8) 0.2097(4) 0.046(1) Uani 1.00 1 d . . . C2 C 0.0372(1) 0.5433(8) 0.1587(4) 0.045(1) Uani 1.00 1 d . . . C3 C 0.0100(1) 0.5858(8) 0.0468(5) 0.043(1) Uani 1.00 1 d . . . C4 C 0.0944(1) 0.1113(8) 0.3861(5) 0.045(1) Uani 1.00 1 d . . . C5 C 0.1266(1) 0.1706(7) 0.5050(4) 0.037(1) Uani 1.00 1 d . . . C6 C 0.1563(1) 0.0138(7) 0.5374(4) 0.041(1) Uani 1.00 1 d . . . C7 C 0.1855(1) 0.0573(8) 0.6484(4) 0.039(1) Uani 1.00 1 d . . . C8 C 0.1860(1) 0.2615(7) 0.7277(4) 0.035(1) Uani 1.00 1 d . . . C9 C 0.1568(1) 0.4210(8) 0.6970(4) 0.040(1) Uani 1.00 1 d . . . C10 C 0.1271(1) 0.3749(7) 0.5850(4) 0.039(1) Uani 1.00 1 d . . . C11 C 0.2178(1) 0.5005(9) 0.9179(5) 0.048(1) Uani 1.00 1 d . . . H1 H 0.047(1) 0.667(8) 0.212(4) 0.04(1) Uiso 1.00 1 c . . . H2 H 0.005(1) 0.73(1) 0.037(6) 0.07(2) Uiso 1.00 1 c . . . H3 H 0.104(1) 0.023(9) 0.321(5) 0.06(1) Uiso 1.00 1 c . . . H4 H 0.074(1) 0.043(8) 0.412(5) 0.05(1) Uiso 1.00 1 c . . . H5 H 0.156(1) -0.119(7) 0.486(4) 0.04(1) Uiso 1.00 1 c . . . H6 H 0.206(1) -0.017(8) 0.669(4) 0.04(1) Uiso 1.00 1 c . . . H7 H 0.157(1) 0.552(9) 0.749(5) 0.05(1) Uiso 1.00 1 c . . . H8 H 0.109(1) 0.508(8) 0.561(4) 0.04(1) Uiso 1.00 1 c . . . H9 H 0.241(1) 0.476(9) 0.982(6) 0.07(1) Uiso 1.00 1 c . . . H10 H 0.223(1) 0.654(9) 0.863(5) 0.07(1) Uiso 1.00 1 c . . . H11 H 0.194(2) 0.526(9) 0.964(5) 0.07(1) Uiso 1.00 1 c . . . 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 O1 0.117(3) 0.041(2) 0.091(3) 0.003(2) -0.067(2) -0.006(2) O2 0.048(2) 0.038(2) 0.035(1) 0.001(1) -0.012(1) -0.002(1) O3 0.045(2) 0.047(2) 0.032(1) 0.005(1) -0.009(1) 0.001(1) C1 0.053(2) 0.039(2) 0.038(2) -0.001(2) -0.010(2) -0.006(2) C2 0.051(2) 0.039(2) 0.038(2) -0.006(2) -0.011(2) -0.007(2) C3 0.042(2) 0.036(2) 0.046(2) 0.003(2) -0.005(2) -0.000(2) C4 0.050(2) 0.036(2) 0.041(2) 0.001(2) -0.010(2) -0.002(2) C5 0.044(2) 0.034(2) 0.030(2) -0.002(2) -0.004(2) 0.001(2) C6 0.055(2) 0.029(2) 0.036(2) 0.007(2) -0.001(2) -0.001(2) C7 0.047(2) 0.037(2) 0.031(2) 0.010(2) -0.000(2) 0.002(2) C8 0.036(2) 0.038(2) 0.028(2) -0.000(2) -0.003(1) 0.008(2) C9 0.044(2) 0.037(2) 0.037(2) 0.003(2) -0.003(2) -0.008(2) C10 0.039(2) 0.040(2) 0.035(2) 0.006(2) -0.002(2) -0.001(2) C11 0.047(2) 0.053(3) 0.037(2) -0.004(2) -0.011(2) -0.003(2) #============================================================================== _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'CrystalStructure' _computing_structure_solution 'SIR92' _computing_structure_refinement 'CRYSTALS' _computing_publication_material 'CrystalStructure Ver. 2.00' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.185(5) yes O2 . C1 . 1.335(4) yes O2 . C4 . 1.431(5) yes O3 . C8 . 1.366(4) yes O3 . C11 . 1.414(5) yes C1 . C2 . 1.458(6) yes C2 . C3 . 1.331(5) yes C2 . H1 . 0.90(4) no C3 . H2 . 0.85(6) no C4 . C5 . 1.502(5) yes C4 . H3 . 0.90(5) no C4 . H4 . 0.90(4) no C5 . C6 . 1.376(5) yes C5 . C10 . 1.372(5) yes C6 . C7 . 1.372(6) yes C6 . H5 . 0.89(4) no C7 . C8 . 1.368(5) yes C7 . H6 . 0.83(4) no C8 . C9 . 1.368(5) yes C9 . C10 . 1.392(5) yes C9 . H7 . 0.89(5) no C10 . H8 . 1.00(4) no C11 . H9 . 0.96(5) no C11 . H10 . 1.04(5) no C11 . H11 . 1.03(5) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O2 . C4 . 116.3(3) yes C8 . O3 . C11 . 117.1(3) yes O1 . C1 . O2 . 121.4(4) yes O1 . C1 . C2 . 127.9(4) yes O2 . C1 . C2 . 110.7(3) yes C1 . C2 . C3 . 125.9(4) yes C1 . C2 . H1 . 115.5(25) no C3 . C2 . H1 . 118.5(25) no C2 . C3 . H2 . 112.4(35) no O2 . C4 . C5 . 108.6(3) yes O2 . C4 . H3 . 111.2(29) no C5 . C4 . H3 . 107.9(30) no O2 . C4 . H4 . 100.6(28) no C5 . C4 . H4 . 116.5(28) no H3 . C4 . H4 . 111.9(40) no C4 . C5 . C6 . 119.5(4) yes C4 . C5 . C10 . 122.2(3) yes C6 . C5 . C10 . 118.4(3) yes C5 . C6 . C7 . 121.2(4) yes C5 . C6 . H5 . 118.3(25) no C7 . C6 . H5 . 120.5(26) no C6 . C7 . C8 . 120.1(4) yes C6 . C7 . H6 . 127.9(29) no C8 . C7 . H6 . 111.4(29) no O3 . C8 . C7 . 115.8(3) yes O3 . C8 . C9 . 124.4(4) yes C7 . C8 . C9 . 119.8(3) yes C8 . C9 . C10 . 119.8(4) yes C8 . C9 . H7 . 120.6(28) no C10 . C9 . H7 . 119.6(28) no C5 . C10 . C9 . 120.7(4) yes C5 . C10 . H8 . 123.6(23) no C9 . C10 . H8 . 115.3(23) no O3 . C11 . H9 . 100.0(31) no O3 . C11 . H10 . 113.6(26) no H9 . C11 . H10 . 103.0(40) no O3 . C11 . H11 . 113.8(29) no H9 . C11 . H11 . 117.1(41) no H10 . C11 . H11 . 108.9(38) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C4 . O2 . C1 . O1 . -1.8(9) yes C4 . O2 . C1 . C2 . 179.9(5) yes C1 . O2 . C4 . C5 . 174.8(5) yes C11 . O3 . C8 . C7 . 179.8(5) yes C11 . O3 . C8 . C9 . -0.1(9) yes O1 . C1 . C2 . C3 . 2.4(1) yes O2 . C1 . C2 . C3 . -179.4(5) yes O2 . C4 . C5 . C6 . -151.1(5) yes O2 . C4 . C5 . C10 . 30.2(6) yes C4 . C5 . C6 . C7 . -177.7(5) yes C10 . C5 . C6 . C7 . 1.1(8) yes C4 . C5 . C10 . C9 . 178.1(5) yes C6 . C5 . C10 . C9 . -0.6(8) yes C5 . C6 . C7 . C8 . -1.2(8) yes C6 . C7 . C8 . O3 . -179.1(5) yes C6 . C7 . C8 . C9 . 0.8(8) yes O3 . C8 . C9 . C10 . 179.6(4) yes C7 . C8 . C9 . C10 . -0.3(8) yes C8 . C9 . C10 . C5 . 0.2(8) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_site_symmetry_1 _geom_contact_atom_site_label_2 _geom_contact_site_symmetry_2 _geom_contact_distance _geom_contact_publ_flag O1 . O2 . 2.198(4) yes O1 . C1 . 1.185(5) yes O1 . C2 1_545 3.234(6) yes O1 . C2 . 2.377(6) yes O1 . C3 1_545 3.312(6) yes O1 . C3 . 2.971(6) yes O1 . C3 2_565 2.954(5) yes O1 . C4 . 2.601(5) yes O1 . H1 1_545 2.59(4) no O1 . H1 . 3.11(4) no O1 . H2 1_545 2.70(5) no O1 . H2 2_565 2.42(5) no O1 . H3 . 2.53(4) no O1 . H4 . 2.51(4) no O1 . H4 6_554 2.94(4) no O1 . H8 6_564 3.43(4) no O2 . C1 . 1.335(4) yes O2 . C2 . 2.297(5) yes O2 . C3 . 3.572(5) yes O2 . C3 6_565 3.542(5) yes O2 . C4 . 1.431(5) yes O2 . C5 . 2.382(4) yes O2 . C9 6_564 3.558(5) yes O2 . C10 . 2.774(4) yes O2 . C10 6_564 3.527(5) yes O2 . H1 . 2.36(4) no O2 . H3 . 1.95(5) no O2 . H4 . 1.82(5) no O2 . H7 6_564 3.10(4) no O2 . H8 . 2.52(4) no O2 . H8 6_564 3.04(4) no O3 . C6 . 3.587(5) yes O3 . C6 6_555 3.579(5) yes O3 . C7 . 2.316(5) yes O3 . C8 . 1.366(4) yes O3 . C9 . 2.419(4) yes O3 . C11 . 1.414(5) yes O3 . C11 4_557 3.435(5) yes O3 . H5 6_555 2.98(4) no O3 . H6 . 2.31(4) no O3 . H6 7_556 3.01(4) no O3 . H7 . 2.62(4) no O3 . H9 . 1.84(5) no O3 . H9 4_557 2.58(5) no O3 . H10 1_545 3.58(5) no O3 . H10 . 2.06(5) no O3 . H10 7_546 3.22(5) no O3 . H11 . 2.06(5) no C1 . C2 . 1.458(6) yes C1 . C3 . 2.485(6) yes C1 . C3 2_565 3.036(6) yes C1 . C4 . 2.350(6) yes C1 . H1 1_545 3.60(4) no C1 . H1 . 2.01(4) no C1 . H2 . 3.19(6) no C1 . H2 2_565 2.81(5) no C1 . H3 . 2.56(5) no C1 . H4 . 2.45(4) no C1 . H8 6_564 2.89(4) no C2 . C2 5_555 3.444(9) yes C2 . C3 . 1.331(5) yes C2 . C3 2_565 2.457(6) yes C2 . C3 5_555 3.529(6) yes C2 . C10 6_564 3.463(6) yes C2 . H1 . 0.90(4) no C2 . H1 5_555 3.55(4) no C2 . H2 . 1.83(6) no C2 . H2 2_565 2.67(5) no C2 . H8 6_564 2.90(4) no C3 . C3 2_565 1.416(8) yes C3 . H1 . 1.93(4) no C3 . H1 2_565 3.24(4) no C3 . H1 5_555 3.37(4) no C3 . H2 . 0.85(6) no C3 . H2 2_565 1.99(6) no C3 . H4 6_564 3.51(4) no C3 . H8 6_564 3.57(4) no C4 . C5 . 1.502(5) yes C4 . C6 . 2.486(6) yes C4 . C10 . 2.517(6) yes C4 . H1 1_545 3.29(4) no C4 . H3 . 0.90(5) no C4 . H4 . 0.90(4) no C4 . H5 . 2.59(4) no C4 . H7 6_564 3.36(5) no C4 . H8 . 2.77(4) no C5 . C6 . 1.376(5) yes C5 . C7 . 2.394(5) yes C5 . C8 . 2.772(5) yes C5 . C9 . 2.402(5) yes C5 . C10 . 1.372(5) yes C5 . H3 . 1.97(5) no C5 . H3 6_555 3.42(5) no C5 . H4 . 2.06(4) no C5 . H5 . 1.96(4) no C5 . H6 . 3.17(4) no C5 . H7 . 3.20(5) no C5 . H7 6_564 3.22(5) no C5 . H8 . 2.10(4) no C5 . H11 6_564 3.06(5) no C6 . C7 . 1.372(6) yes C6 . C8 . 2.374(5) yes C6 . C9 . 2.736(6) yes C6 . C10 . 2.359(6) yes C6 . H3 . 2.53(5) no C6 . H3 6_555 3.56(5) no C6 . H4 . 2.99(4) no C6 . H5 . 0.89(4) no C6 . H6 . 1.99(4) no C6 . H7 1_545 3.27(5) no C6 . H8 1_545 3.34(4) no C6 . H8 . 3.29(4) no C6 . H11 6_554 3.44(5) no C6 . H11 6_564 3.06(5) no C7 . C8 . 1.368(5) yes C7 . C9 . 2.367(6) yes C7 . C10 . 2.739(6) yes C7 . H5 . 1.98(4) no C7 . H5 6_555 3.57(4) no C7 . H6 . 0.83(4) no C7 . H7 1_545 3.22(5) no C7 . H7 . 3.17(5) no C7 . H9 7_546 3.14(5) no C7 . H10 1_545 3.17(5) no C7 . H10 7_546 3.37(5) no C7 . H11 6_564 2.97(5) no C8 . C9 . 1.368(5) yes C8 . C10 . 2.388(5) yes C8 . C11 . 2.371(5) yes C8 . C11 6_564 3.595(6) yes C8 . H5 . 3.18(4) no C8 . H5 6_555 2.96(4) no C8 . H6 . 1.84(4) no C8 . H7 . 1.97(5) no C8 . H8 . 3.26(4) no C8 . H9 . 3.09(5) no C8 . H10 . 2.76(5) no C8 . H10 7_546 3.60(5) no C8 . H11 . 2.65(5) no C8 . H11 6_564 2.84(5) no C9 . C10 . 1.392(5) yes C9 . C11 . 2.786(5) yes C9 . H3 6_555 3.47(5) no C9 . H5 1_565 3.26(4) no C9 . H5 6_555 3.23(4) no C9 . H6 . 3.06(4) no C9 . H7 . 0.89(5) no C9 . H8 . 2.03(4) no C9 . H10 . 2.91(5) no C9 . H11 . 2.71(5) no C9 . H11 6_564 2.81(5) no C10 . H1 6_565 3.32(4) no C10 . H3 . 3.18(5) no C10 . H3 6_555 3.37(5) no C10 . H4 . 2.95(4) no C10 . H5 . 3.15(4) no C10 . H5 1_565 3.21(4) no C10 . H6 . 3.56(4) no C10 . H7 . 1.99(5) no C10 . H7 6_564 3.56(4) no C10 . H8 . 1.00(4) no C10 . H11 6_564 2.91(6) no C11 . H5 6_555 3.24(4) no C11 . H6 1_565 3.56(4) no C11 . H6 7_556 3.02(4) no C11 . H7 . 2.50(4) no C11 . H9 . 0.96(5) no C11 . H9 4_557 3.12(5) no C11 . H9 4_567 3.34(5) no C11 . H10 . 1.04(5) no C11 . H10 4_567 3.33(5) no C11 . H11 . 1.03(5) no H1 . H2 . 2.08(6) no H1 . H2 2_565 3.54(7) no H1 . H2 5_555 3.30(7) no H1 . H3 1_565 2.90(6) no H1 . H4 1_565 2.88(6) no H1 . H4 6_564 3.56(5) no H1 . H8 6_564 3.00(5) no H2 . H2 2_565 2.71(11) no H2 . H2 2_575 3.07(12) no H2 . H4 5_565 3.43(7) no H2 . H4 6_564 3.21(7) no H3 . H4 . 1.49(6) no H3 . H5 . 2.36(6) no H3 . H7 6_564 3.19(6) no H3 . H8 . 3.53(6) no H4 . H5 . 3.04(6) no H4 . H8 1_545 3.45(6) no H4 . H8 . 3.11(6) no H5 . H6 . 2.34(6) no H5 . H7 1_545 3.10(6) no H5 . H7 6_554 3.31(6) no H5 . H8 1_545 2.86(6) no H5 . H11 6_554 2.70(7) no H6 . H7 1_545 3.16(6) no H6 . H9 4_557 3.52(6) no H6 . H9 7_546 2.58(6) no H6 . H9 6_554 3.50(7) no H6 . H10 1_545 2.60(7) no H6 . H10 7_546 2.82(6) no H6 . H11 6_554 3.44(7) no H6 . H11 6_564 3.36(7) no H7 . H8 . 2.26(6) no H7 . H9 . 3.46(7) no H7 . H10 . 2.50(6) no H7 . H11 . 2.24(7) no H7 . H11 6_564 3.27(7) no H8 . H11 6_564 3.38(7) no H9 . H9 4_557 2.62(11) no H9 . H9 4_567 3.1(1) no H9 . H10 . 1.56(7) no H9 . H10 4_567 2.73(7) no H9 . H11 . 1.69(7) no H10 . H10 4_567 3.2(1) no H10 . H11 . 1.68(6) no #===END data_2 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H22 O6 ' _chemical_formula_moiety 'C22 H22 O6 ' _chemical_formula_weight 382.41 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' 'x+1/2,y+1/2,z' '-x+1/2,-y+1/2,-z' '-x,y,-z+1/2' 'x,-y,z+1/2' '-x+1/2,y+1/2,-z+1/2' 'x+1/2,-y+1/2,z+1/2' #------------------------------------------------------------------------------ _cell_length_a 35.644(4) _cell_length_b 5.6923(4) _cell_length_c 9.7803(6) _cell_angle_alpha 90 _cell_angle_beta 100.533(3) _cell_angle_gamma 90 _cell_volume 1951.0(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6426 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.0 _cell_measurement_temperature 203.1 #------------------------------------------------------------------------------ _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.00 _diffrn_reflns_number 7791 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_theta_max 27.37 _diffrn_measured_fraction_theta_max 0.9413 _diffrn_reflns_theta_full 27.37 _diffrn_measured_fraction_theta_full 0.9413 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 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 2308 _reflns_number_gt 1720 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1000 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1726 _refine_ls_number_parameters 165 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.010Fo^2^ + 1.000\s^2^(Fo)]' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.18 _refine_diff_density_min -0.25 _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' 0.006 0.003 ; 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' 0.017 0.010 ; 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 O1 O 0.04321(6) -0.0015(3) -0.3125(2) 0.0559(5) Uani 1.00 1 d . . . O2 O 0.07796(4) 0.2480(2) -0.1648(1) 0.0365(4) Uani 1.00 1 d . . . O3 O 0.21693(4) 0.3113(3) 0.3457(1) 0.0395(4) Uani 1.00 1 d . . . C1 C 0.05119(6) 0.1960(3) -0.2754(2) 0.0328(5) Uani 1.00 1 d . . . C2 C 0.03412(6) 0.4090(3) -0.3451(2) 0.0338(5) Uani 1.00 1 d . . . C3 C 0.00878(6) 0.3971(3) -0.4644(2) 0.0335(5) Uani 1.00 1 d . . . C4 C 0.09581(7) 0.0481(4) -0.0882(2) 0.0420(5) Uani 1.00 1 d . . . C5 C 0.12763(6) 0.1331(3) 0.0243(2) 0.0319(5) Uani 1.00 1 d . . . C6 C 0.16064(6) -0.0018(3) 0.0584(2) 0.0354(5) Uani 1.00 1 d . . . C7 C 0.18973(6) 0.0618(3) 0.1657(2) 0.0349(5) Uani 1.00 1 d . . . C8 C 0.18655(5) 0.2638(3) 0.2418(2) 0.0298(4) Uani 1.00 1 d . . . C9 C 0.15400(6) 0.4033(3) 0.2091(2) 0.0343(5) Uani 1.00 1 d . . . C10 C 0.12485(6) 0.3352(4) 0.1004(2) 0.0362(5) Uani 1.00 1 d . . . C11 C 0.21499(7) 0.5154(4) 0.4274(2) 0.0436(6) Uani 1.00 1 d . . . H1 H 0.0410(7) 0.556(4) -0.299(2) 0.044(6) Uiso 1.00 1 c . . . H2 H 0.0028(8) 0.242(5) -0.510(3) 0.048(7) Uiso 1.00 1 c . . . H3 H 0.105(1) -0.050(6) -0.153(4) 0.08(1) Uiso 1.00 1 c . . . H4 H 0.0768(8) -0.062(4) -0.050(3) 0.046(6) Uiso 1.00 1 c . . . H5 H 0.16316(6) -0.1406(3) 0.0070(2) 0.042(1) Uiso 1.00 1 c . . . H6 H 0.2128(8) -0.030(4) 0.192(3) 0.048(7) Uiso 1.00 1 c . . . H7 H 0.1500(7) 0.548(4) 0.257(3) 0.042(6) Uiso 1.00 1 c . . . H8 H 0.10262(6) 0.4299(4) 0.0784(2) 0.042(1) Uiso 1.00 1 c . . . H9 H 0.238(1) 0.531(5) 0.505(3) 0.069(9) Uiso 1.00 1 c . . . H10 H 0.2134(9) 0.669(5) 0.373(3) 0.065(8) Uiso 1.00 1 c . . . H11 H 0.192(1) 0.506(6) 0.468(4) 0.09(1) Uiso 1.00 1 c . . . 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 O1 0.065(1) 0.0320(8) 0.057(1) -0.0056(7) -0.0247(9) -0.0023(7) O2 0.0400(9) 0.0310(7) 0.0322(7) -0.0009(6) -0.0104(6) -0.0001(6) O3 0.0334(8) 0.0458(9) 0.0347(7) -0.0001(6) -0.0067(6) -0.0034(6) C1 0.033(1) 0.0336(9) 0.0281(8) -0.0033(7) -0.0034(7) -0.0007(7) C2 0.032(1) 0.033(1) 0.034(1) -0.0034(7) -0.0025(7) -0.0003(8) C3 0.033(1) 0.0321(9) 0.0328(9) -0.0027(7) -0.0016(7) 0.0005(7) C4 0.048(1) 0.032(1) 0.037(1) 0.0021(9) -0.0149(9) 0.0004(8) C5 0.034(1) 0.0320(9) 0.0268(8) 0.0012(8) -0.0030(7) 0.0006(7) C6 0.045(1) 0.0280(9) 0.0310(9) 0.0092(8) 0.0005(8) 0.0006(7) C7 0.034(1) 0.036(1) 0.0325(9) 0.0096(8) 0.0007(8) 0.0028(8) C8 0.0271(9) 0.0348(9) 0.0262(9) -0.0016(7) 0.0013(7) 0.0044(7) C9 0.033(1) 0.0339(9) 0.0345(9) 0.0045(8) 0.0009(7) -0.0072(8) C10 0.031(1) 0.037(1) 0.037(1) 0.0068(8) -0.0029(8) -0.0038(8) C11 0.047(1) 0.044(1) 0.035(1) -0.011(1) -0.0033(9) -0.0048(9) #============================================================================== _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'CrystalStructure' _computing_structure_solution 'SIR92' _computing_structure_refinement 'CRYSTALS' _computing_publication_material 'CrystalStructure Ver. 2.00' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.200(2) yes O2 . C1 . 1.338(2) yes O2 . C4 . 1.445(2) yes O3 . C8 . 1.370(2) yes O3 . C11 . 1.418(3) yes C1 . C2 . 1.467(3) yes C2 . C3 . 1.340(3) yes C2 . H1 . 0.96(2) no C3 . H2 . 0.99(3) no C4 . C5 . 1.508(3) yes C4 . H3 . 0.94(4) no C4 . H4 . 1.04(3) no C5 . C6 . 1.394(3) yes C5 . C10 . 1.384(3) yes C6 . C7 . 1.381(3) yes C6 . H5 . 0.950 no C7 . C8 . 1.385(3) yes C7 . H6 . 0.97(3) no C8 . C9 . 1.394(3) yes C9 . C10 . 1.399(3) yes C9 . H7 . 0.97(3) no C10 . H8 . 0.94991(7) no C11 . H9 . 1.01(3) no C11 . H10 . 1.02(3) no C11 . H11 . 0.96(4) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O2 . C4 . 115.22(15) yes C8 . O3 . C11 . 117.79(16) yes O1 . C1 . O2 . 123.11(18) yes O1 . C1 . C2 . 125.36(18) yes O2 . C1 . C2 . 111.51(16) yes C1 . C2 . C3 . 121.26(17) yes C1 . C2 . H1 . 117.1(14) no C3 . C2 . H1 . 121.6(14) no C2 . C3 . H2 . 119.4(15) no O2 . C4 . C5 . 109.05(16) yes O2 . C4 . H3 . 107.0(21) no C5 . C4 . H3 . 112.4(22) no O2 . C4 . H4 . 113.9(14) no C5 . C4 . H4 . 112.7(14) no H3 . C4 . H4 . 101.6(25) no C4 . C5 . C6 . 119.19(17) yes C4 . C5 . C10 . 122.75(18) yes C6 . C5 . C10 . 117.99(16) yes C5 . C6 . C7 . 121.42(17) yes C5 . C6 . H5 . 119.25(11) no C7 . C6 . H5 . 119.33(11) no C6 . C7 . C8 . 120.12(18) yes C6 . C7 . H6 . 122.8(15) no C8 . C7 . H6 . 117.0(15) no O3 . C8 . C7 . 115.56(17) yes O3 . C8 . C9 . 124.73(17) yes C7 . C8 . C9 . 119.71(17) yes C8 . C9 . C10 . 119.23(17) yes C8 . C9 . H7 . 124.1(15) no C10 . C9 . H7 . 116.7(15) no C5 . C10 . C9 . 121.53(17) yes C5 . C10 . H8 . 119.22(11) no C9 . C10 . H8 . 119.25(11) no O3 . C11 . H9 . 112.3(18) no O3 . C11 . H10 . 114.1(17) no H9 . C11 . H10 . 106.3(25) no O3 . C11 . H11 . 108.7(21) no H9 . C11 . H11 . 108.3(28) no H10 . C11 . H11 . 107.0(27) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C4 . O2 . C1 . O1 . -2.5(4) yes C4 . O2 . C1 . C2 . 178.9(2) yes C1 . O2 . C4 . C5 . 174.7(2) yes C11 . O3 . C8 . C7 . -179.6(3) yes C11 . O3 . C8 . C9 . 0.9(4) yes O1 . C1 . C2 . C3 . -3.7(4) yes O2 . C1 . C2 . C3 . 174.8(2) yes O2 . C4 . C5 . C6 . -144.5(2) yes O2 . C4 . C5 . C10 . 38.7(3) yes C4 . C5 . C6 . C7 . -176.4(3) yes C10 . C5 . C6 . C7 . 0.5(4) yes C4 . C5 . C10 . C9 . 176.6(3) yes C6 . C5 . C10 . C9 . -0.3(4) yes C5 . C6 . C7 . C8 . -0.2(4) yes C6 . C7 . C8 . O3 . -179.9(2) yes C6 . C7 . C8 . C9 . -0.4(4) yes O3 . C8 . C9 . C10 . -179.9(2) yes C7 . C8 . C9 . C10 . 0.7(4) yes C8 . C9 . C10 . C5 . -0.3(4) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_site_symmetry_1 _geom_contact_atom_site_label_2 _geom_contact_site_symmetry_2 _geom_contact_distance _geom_contact_publ_flag O1 . O1 5_554 3.516(5) yes O1 . O2 . 2.2328(19) yes O1 . C1 . 1.200(2) yes O1 . C2 1_545 3.381(2) yes O1 . C2 . 2.373(2) yes O1 . C3 . 2.863(2) yes O1 . C3 2_554 3.433(3) yes O1 . C4 . 2.627(3) yes O1 . C4 6_554 3.564(4) yes O1 . H1 1_545 2.53(2) no O1 . H1 . 3.18(2) no O1 . H2 . 2.59(3) no O1 . H2 2_554 2.56(3) no O1 . H3 . 2.46(4) no O1 . H4 . 2.65(2) no O1 . H4 6_554 2.83(3) no O1 . H8 6_554 3.521(3) no O2 . C1 . 1.338(2) yes O2 . C2 . 2.320(2) yes O2 . C3 . 3.570(2) yes O2 . C4 . 1.445(2) yes O2 . C5 . 2.405(2) yes O2 . C10 . 2.860(2) yes O2 . H1 . 2.43(2) no O2 . H3 . 1.94(3) no O2 . H4 . 2.09(3) no O2 . H7 6_564 3.04(3) no O2 . H8 . 2.595(2) no O2 . H8 6_564 3.355(2) no O3 . O3 4_556 3.543(3) yes O3 . C7 . 2.331(2) yes O3 . C8 . 1.370(2) yes O3 . C9 . 2.449(2) yes O3 . C11 . 1.418(3) yes O3 . C11 4_556 3.507(3) yes O3 . H5 6_555 2.865(3) no O3 . H6 . 2.44(3) no O3 . H6 7_555 2.75(3) no O3 . H7 . 2.74(3) no O3 . H9 . 2.03(3) no O3 . H9 4_556 2.77(3) no O3 . H10 . 2.06(3) no O3 . H11 . 1.95(4) no C1 . C2 . 1.467(3) yes C1 . C3 . 2.448(3) yes C1 . C4 . 2.351(3) yes C1 . H1 . 2.08(2) no C1 . H2 . 2.62(3) no C1 . H2 2_554 3.59(3) no C1 . H3 . 2.49(4) no C1 . H4 . 2.66(2) no C1 . H4 6_554 3.09(3) no C1 . H8 6_564 3.302(3) no C2 . C2 5_554 3.321(4) yes C2 . C3 . 1.340(3) yes C2 . C3 2_564 2.447(3) yes C2 . H1 . 0.96(2) no C2 . H1 5_554 3.35(3) no C2 . H2 . 2.02(3) no C2 . H2 2_564 2.65(3) no C2 . H4 6_554 3.37(3) no C2 . H8 6_564 2.834(3) no C3 . C3 2_564 1.446(4) yes C3 . H1 . 2.01(2) no C3 . H1 2_564 2.66(2) no C3 . H1 5_554 3.51(3) no C3 . H2 . 0.99(3) no C3 . H2 2_564 2.10(3) no C3 . H4 6_554 3.31(3) no C3 . H8 6_564 3.438(3) no C4 . C5 . 1.508(3) yes C4 . C6 . 2.503(3) yes C4 . C10 . 2.539(3) yes C4 . H3 . 0.94(4) no C4 . H4 . 1.04(3) no C4 . H5 . 2.640(3) no C4 . H7 6_564 3.52(3) no C4 . H8 . 2.700(3) no C5 . C6 . 1.394(3) yes C5 . C7 . 2.420(3) yes C5 . C8 . 2.803(3) yes C5 . C9 . 2.428(2) yes C5 . C10 . 1.384(3) yes C5 . H3 . 2.06(4) no C5 . H3 6_555 3.44(4) no C5 . H4 . 2.14(3) no C5 . H5 . 2.034(3) no C5 . H6 . 3.31(3) no C5 . H7 . 3.28(3) no C5 . H7 6_564 3.39(3) no C5 . H8 . 2.025(3) no C5 . H11 6_564 3.21(4) no C6 . C7 . 1.381(3) yes C6 . C8 . 2.398(2) yes C6 . C9 . 2.770(3) yes C6 . C10 . 2.381(3) yes C6 . H3 . 2.61(4) no C6 . H4 . 3.00(3) no C6 . H5 . 0.950 no C6 . H6 . 2.07(3) no C6 . H7 1_545 3.28(2) no C6 . H8 . 3.240(3) no C6 . H10 6_564 3.42(3) no C6 . H11 6_554 3.27(4) no C6 . H11 6_564 3.22(4) no C7 . C8 . 1.385(3) yes C7 . C9 . 2.403(3) yes C7 . C10 . 2.764(3) yes C7 . C11 6_564 3.578(3) yes C7 . H5 . 2.024(3) no C7 . H6 . 0.97(3) no C7 . H7 1_545 3.44(2) no C7 . H7 . 3.30(3) no C7 . H9 7_545 3.33(3) no C7 . H9 6_564 3.43(3) no C7 . H10 1_545 3.03(3) no C7 . H10 7_545 3.59(3) no C7 . H10 6_564 3.49(3) no C7 . H11 6_564 3.14(4) no C8 . C9 . 1.394(3) yes C8 . C10 . 2.409(3) yes C8 . C11 . 2.387(3) yes C8 . H3 6_555 3.49(4) no C8 . H5 . 3.251(2) no C8 . H5 6_555 2.950(2) no C8 . H6 . 2.02(3) no C8 . H7 . 2.10(3) no C8 . H8 . 3.264(3) no C8 . H9 . 3.25(3) no C8 . H9 6_564 3.41(3) no C8 . H10 . 2.72(3) no C8 . H11 . 2.58(4) no C8 . H11 6_564 3.02(4) no C9 . C10 . 1.399(3) yes C9 . C11 . 2.828(3) yes C9 . H3 6_555 3.13(4) no C9 . H5 1_565 3.315(3) no C9 . H5 6_555 3.238(3) no C9 . H6 . 3.26(3) no C9 . H7 . 0.97(3) no C9 . H8 . 2.039(3) no C9 . H10 . 2.84(3) no C9 . H11 . 2.71(3) no C9 . H11 6_564 2.98(4) no C10 . H1 6_565 3.37(3) no C10 . H3 . 3.29(4) no C10 . H3 6_555 3.10(4) no C10 . H4 . 3.05(3) no C10 . H5 . 3.239(3) no C10 . H5 1_565 3.473(3) no C10 . H7 . 2.03(3) no C10 . H8 . 0.94991(7) no C10 . H11 6_564 3.07(4) no C11 . H5 6_555 3.016(3) no C11 . H6 1_565 3.46(3) no C11 . H6 7_555 3.03(3) no C11 . H7 . 2.60(2) no C11 . H9 . 1.01(3) no C11 . H9 4_556 3.54(3) no C11 . H9 4_566 3.09(3) no C11 . H10 . 1.02(3) no C11 . H10 4_566 3.43(3) no C11 . H11 . 0.96(4) no H1 . H1 5_554 3.24(5) no H1 . H2 . 2.87(4) no H1 . H2 2_564 2.48(4) no H1 . H2 6_565 3.55(4) no H1 . H3 1_565 3.32(4) no H1 . H4 1_565 3.34(3) no H1 . H8 6_564 2.69(3) no H2 . H2 2_554 2.78(5) no H2 . H2 2_564 2.95(5) no H2 . H4 5_554 3.46(4) no H2 . H4 6_554 2.92(4) no H3 . H4 . 1.54(4) no H3 . H5 . 2.42(4) no H3 . H7 6_554 3.45(4) no H3 . H7 6_564 3.48(4) no H3 . H8 . 3.56(4) no H3 . H8 6_554 3.39(4) no H4 . H5 . 3.06(3) no H4 . H8 1_545 3.22(3) no H4 . H8 . 3.14(3) no H5 . H6 . 2.37(2) no H5 . H7 1_545 3.13(2) no H5 . H7 6_554 3.34(2) no H5 . H8 1_545 3.417(3) no H5 . H9 6_554 3.47(3) no H5 . H11 6_554 2.39(4) no H6 . H7 1_545 3.42(4) no H6 . H9 4_556 3.16(4) no H6 . H9 7_545 2.86(4) no H6 . H9 6_554 3.59(4) no H6 . H9 6_564 3.58(4) no H6 . H10 1_545 2.46(4) no H6 . H10 7_545 3.03(4) no H6 . H11 6_554 3.48(5) no H7 . H8 . 2.30(2) no H7 . H9 . 3.59(4) no H7 . H10 . 2.43(4) no H7 . H11 . 2.33(4) no H7 . H11 6_564 3.46(5) no H8 . H11 6_564 3.58(4) no H9 . H9 4_556 3.32(6) no H9 . H9 4_566 2.65(6) no H9 . H10 . 1.62(4) no H9 . H10 4_566 2.57(5) no H9 . H11 . 1.60(5) no H9 . H11 4_566 3.60(5) no H10 . H10 4_566 3.39(6) no H10 . H11 . 1.59(5) no #===END data_3 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H22 O6 ' _chemical_formula_moiety 'C22 H22 O6 ' _chemical_formula_weight 382.41 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' #------------------------------------------------------------------------------ _cell_length_a 6.6919(1) _cell_length_b 10.784(1) _cell_length_c 14.0070(8) _cell_angle_alpha 107.237(5) _cell_angle_beta 99.272(3) _cell_angle_gamma 93.847(4) _cell_volume 945.7(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4669 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 203.1 #------------------------------------------------------------------------------ _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 7491 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9323 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.9300 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 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 4035 _reflns_number_gt 2607 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.1360 _refine_ls_wR_factor_ref 0.2090 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2635 _refine_ls_number_parameters 269 _refine_ls_goodness_of_fit_ref 2.424 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.005Fo^2^ + 1.000\s^2^(Fo)]' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 1.41 _refine_diff_density_min -0.63 _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' 0.006 0.003 ; 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' 0.017 0.010 ; 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 O1 O -0.8688(8) 0.1469(7) 0.3521(5) 0.088(2) Uani 1.00 1 d . . . O2 O -1.0649(6) 0.3121(4) 0.3653(4) 0.057(1) Uani 1.00 1 d . . . O3 O -0.2145(7) 0.1483(6) 0.5145(4) 0.070(2) Uani 1.00 1 d . . . O4 O 0.0090(6) 0.2402(4) 0.6588(3) 0.047(1) Uani 1.00 1 d . . . O5 O -1.777(1) 0.5058(9) 0.0936(6) 0.132(3) Uani 1.00 1 d . . . O6 O 0.757(1) 0.1177(9) 0.9667(6) 0.131(3) Uani 1.00 1 d . . . C1 C -0.895(1) 0.259(1) 0.3939(7) 0.069(3) Uani 1.00 1 d . . . C2 C -0.765(1) 0.3492(9) 0.4788(7) 0.077(3) Uani 1.00 1 d . . . C3 C -0.562(2) 0.3076(8) 0.5110(6) 0.082(3) Uani 1.00 1 d . . . C4 C -0.426(1) 0.386(1) 0.5897(8) 0.085(3) Uani 1.00 1 d . . . C5 C -0.256(1) 0.3558(9) 0.6270(6) 0.071(3) Uani 1.00 1 d . . . C6 C -0.1565(9) 0.2351(7) 0.5910(5) 0.050(2) Uani 1.00 1 d . . . C7 C -1.211(1) 0.2237(6) 0.2828(6) 0.065(2) Uani 1.00 1 d . . . C8 C 0.1189(9) 0.1254(5) 0.6314(4) 0.041(1) Uani 1.00 1 d . . . C9 C -1.3533(9) 0.2987(6) 0.2367(4) 0.045(2) Uani 1.00 1 d . . . C10 C -1.5601(9) 0.2590(5) 0.2153(4) 0.044(2) Uani 1.00 1 d . . . C11 C -1.6949(9) 0.3250(6) 0.1669(5) 0.050(2) Uani 1.00 1 d . . . C12 C -1.624(1) 0.4344(7) 0.1435(5) 0.055(2) Uani 1.00 1 d . . . C13 C -1.420(1) 0.4739(6) 0.1662(5) 0.059(2) Uani 1.00 1 d . . . C14 C -1.281(1) 0.4085(6) 0.2137(6) 0.057(2) Uani 1.00 1 d . . . C15 C 0.2844(8) 0.1325(5) 0.7205(4) 0.037(1) Uani 1.00 1 d . . . C16 C 0.4713(9) 0.0965(6) 0.7015(5) 0.047(2) Uani 1.00 1 d . . . C17 C 0.6251(9) 0.0908(6) 0.7801(5) 0.048(2) Uani 1.00 1 d . . . C18 C 0.592(1) 0.1235(6) 0.8792(5) 0.052(2) Uani 1.00 1 d . . . C19 C 0.402(1) 0.1622(7) 0.8976(5) 0.056(2) Uani 1.00 1 d . . . C20 C 0.2544(9) 0.1678(6) 0.8197(4) 0.047(2) Uani 1.00 1 d . . . H1 H -0.803(1) 0.4319(9) 0.5124(7) 0.101(4) Uiso 1.00 1 c . . . H2 H -0.533(9) 0.209(6) 0.461(4) 0.05(2) Uiso 1.00 1 c . . . H3 H -0.459(1) 0.471(1) 0.6211(8) 0.113(5) Uiso 1.00 1 c . . . H4 H -0.182(1) 0.4198(9) 0.6868(6) 0.095(4) Uiso 1.00 1 c . . . H5 H -1.141(1) 0.1760(6) 0.2323(6) 0.077(3) Uiso 1.00 1 c . . . H6 H -1.284(1) 0.1645(6) 0.3068(6) 0.077(3) Uiso 1.00 1 c . . . H7 H 0.202(9) 0.121(6) 0.563(4) 0.05(2) Uiso 1.00 1 c . . . H8 H 0.024(7) 0.055(5) 0.631(3) 0.02(1) Uiso 1.00 1 c . . . H9 H -1.634(8) 0.176(5) 0.224(4) 0.03(1) Uiso 1.00 1 c . . . H10 H -1.8367(9) 0.2949(6) 0.1502(5) 0.058(2) Uiso 1.00 1 c . . . H11 H -1.371(1) 0.5475(6) 0.1490(5) 0.075(3) Uiso 1.00 1 c . . . H12 H -1.14(1) 0.471(7) 0.256(5) 0.06(2) Uiso 1.00 1 c . . . H13 H 0.4958(9) 0.0743(6) 0.6338(5) 0.056(2) Uiso 1.00 1 c . . . H14 H 0.75(1) 0.061(6) 0.761(5) 0.05(2) Uiso 1.00 1 c . . . H15 H 0.377(1) 0.1864(7) 0.9651(5) 0.066(2) Uiso 1.00 1 c . . . H16 H 0.1271(9) 0.1949(6) 0.8336(4) 0.058(2) Uiso 1.00 1 c . . . 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 O1 0.067(3) 0.101(5) 0.134(5) 0.051(3) 0.043(3) 0.072(4) O2 0.043(2) 0.058(3) 0.073(3) 0.016(2) -0.002(2) 0.032(2) O3 0.057(3) 0.091(4) 0.053(3) 0.014(3) -0.010(2) 0.017(3) O4 0.042(2) 0.044(2) 0.051(2) 0.010(2) -0.002(2) 0.014(2) O5 0.144(7) 0.149(7) 0.114(6) 0.039(6) 0.006(5) 0.064(5) O6 0.140(7) 0.147(7) 0.095(5) 0.032(6) -0.014(5) 0.035(5) C1 0.050(4) 0.100(6) 0.083(5) 0.012(4) 0.019(4) 0.062(5) C2 0.069(5) 0.098(6) 0.086(5) 0.005(5) 0.006(4) 0.066(5) C3 0.135(8) 0.053(4) 0.067(5) 0.009(5) 0.050(6) 0.015(4) C4 0.054(5) 0.112(8) 0.115(7) 0.021(5) 0.013(5) 0.073(7) C5 0.060(4) 0.095(6) 0.081(5) 0.035(4) 0.024(4) 0.052(5) C6 0.042(3) 0.068(4) 0.048(4) 0.010(3) 0.008(3) 0.032(3) C7 0.053(4) 0.045(4) 0.094(5) 0.016(3) 0.001(4) 0.022(4) C8 0.047(3) 0.034(3) 0.039(3) 0.011(2) -0.001(2) 0.008(2) C9 0.045(3) 0.040(3) 0.048(3) 0.011(2) 0.009(3) 0.009(3) C10 0.052(3) 0.035(3) 0.043(3) 0.003(3) 0.014(3) 0.007(2) C11 0.043(3) 0.054(4) 0.049(3) 0.005(3) 0.003(3) 0.011(3) C12 0.060(4) 0.066(4) 0.043(3) 0.022(3) 0.005(3) 0.022(3) C13 0.073(5) 0.051(4) 0.063(4) 0.005(3) 0.013(3) 0.031(3) C14 0.046(4) 0.050(4) 0.080(5) 0.005(3) 0.009(3) 0.027(3) C15 0.040(3) 0.027(2) 0.042(3) 0.005(2) 0.004(2) 0.009(2) C16 0.047(3) 0.041(3) 0.051(3) 0.004(3) 0.016(3) 0.006(3) C17 0.037(3) 0.049(3) 0.060(4) 0.012(3) 0.007(3) 0.018(3) C18 0.052(4) 0.044(3) 0.052(4) 0.009(3) -0.005(3) 0.012(3) C19 0.069(4) 0.060(4) 0.036(3) 0.012(3) 0.010(3) 0.011(3) C20 0.046(3) 0.046(3) 0.052(3) 0.020(3) 0.014(3) 0.016(3) #============================================================================== _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'CrystalStructure' _computing_structure_solution 'SIR92' _computing_structure_refinement 'CRYSTALS' _computing_publication_material 'CrystalStructure Ver. 2.00' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.216(11) yes O2 . C1 . 1.363(8) yes O2 . C7 . 1.434(8) yes O3 . C6 . 1.183(8) yes O4 . C6 . 1.324(7) yes O4 . C8 . 1.467(7) yes O5 . C12 . 1.522(9) yes O6 . C18 . 1.530(9) yes C1 . C2 . 1.409(12) yes C2 . C3 . 1.499(13) yes C2 . H1 . 0.94998(8) no C3 . C4 . 1.333(12) yes C3 . H2 . 1.13(6) no C4 . C5 . 1.28(1) yes C4 . H3 . 0.94998(9) no C5 . C6 . 1.49(1) yes C5 . H4 . 0.95001(8) no C7 . C9 . 1.482(8) yes C7 . H5 . 0.94999(5) no C7 . H6 . 0.95005(6) no C8 . C15 . 1.509(7) yes C8 . H7 . 1.17(6) no C8 . H8 . 0.96(5) no C9 . C10 . 1.379(8) yes C9 . C14 . 1.394(8) yes C10 . C11 . 1.399(8) yes C10 . H9 . 1.05(5) no C11 . C12 . 1.387(9) yes C11 . H10 . 0.950 no C12 . C13 . 1.359(9) yes C13 . C14 . 1.407(9) yes C13 . H11 . 0.94996(7) no C14 . H12 . 1.09(7) no C15 . C16 . 1.377(8) yes C15 . C20 . 1.380(8) yes C16 . C17 . 1.401(8) yes C16 . H13 . 0.94998(6) no C17 . C18 . 1.384(9) yes C17 . H14 . 0.95(6) no C18 . C19 . 1.406(9) yes C19 . C20 . 1.366(8) yes C19 . H15 . 0.95002(6) no C20 . H16 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O2 . C7 . 114.2(6) yes C6 . O4 . C8 . 113.7(5) yes O1 . C1 . O2 . 122.7(8) yes O1 . C1 . C2 . 126.3(8) yes O2 . C1 . C2 . 110.9(8) yes C1 . C2 . C3 . 116.0(8) yes C1 . C2 . H1 . 121.6(5) no C3 . C2 . H1 . 122.4(5) no C2 . C3 . C4 . 121.0(8) yes C2 . C3 . H2 . 114.8(32) no C4 . C3 . H2 . 124.1(33) no C3 . C4 . C5 . 125.4(10) yes C3 . C4 . H3 . 117.2(6) no C5 . C4 . H3 . 117.3(7) no C4 . C5 . C6 . 129.8(9) yes C4 . C5 . H4 . 115.1(7) no C6 . C5 . H4 . 115.0(4) no O3 . C6 . O4 . 125.0(6) yes O3 . C6 . C5 . 126.0(6) yes O4 . C6 . C5 . 109.0(6) yes O2 . C7 . C9 . 109.6(5) yes O2 . C7 . H5 . 109.3(4) no C9 . C7 . H5 . 108.7(4) no O2 . C7 . H6 . 110.0(4) no C9 . C7 . H6 . 109.8(4) no H5 . C7 . H6 . 109.456(7) no O4 . C8 . C15 . 108.9(4) yes O4 . C8 . H7 . 113.2(28) no C15 . C8 . H7 . 105.7(28) no O4 . C8 . H8 . 103.8(28) no C15 . C8 . H8 . 102.1(27) no H7 . C8 . H8 . 122.2(41) no C7 . C9 . C10 . 119.9(6) yes C7 . C9 . C14 . 120.8(6) yes C10 . C9 . C14 . 119.4(5) yes C9 . C10 . C11 . 120.2(5) yes C9 . C10 . H9 . 127.3(27) no C11 . C10 . H9 . 112.2(27) no C10 . C11 . C12 . 120.8(6) yes C10 . C11 . H10 . 119.5(3) no C12 . C11 . H10 . 119.6(4) no O5 . C12 . C11 . 119.2(6) yes O5 . C12 . C13 . 122.2(6) yes C11 . C12 . C13 . 118.5(5) yes C12 . C13 . C14 . 121.9(6) yes C12 . C13 . H11 . 119.0(4) no C14 . C13 . H11 . 119.1(4) no C9 . C14 . C13 . 119.1(6) yes C9 . C14 . H12 . 122.6(34) no C13 . C14 . H12 . 113.4(35) no C8 . C15 . C16 . 118.5(5) yes C8 . C15 . C20 . 123.0(5) yes C16 . C15 . C20 . 118.5(5) yes C15 . C16 . C17 . 121.0(5) yes C15 . C16 . H13 . 119.5(3) no C17 . C16 . H13 . 119.5(3) no C16 . C17 . C18 . 120.2(5) yes C16 . C17 . H14 . 116.7(37) no C18 . C17 . H14 . 123.1(36) no O6 . C18 . C17 . 121.4(6) yes O6 . C18 . C19 . 120.5(6) yes C17 . C18 . C19 . 118.0(5) yes C18 . C19 . C20 . 120.8(5) yes C18 . C19 . H15 . 119.6(4) no C20 . C19 . H15 . 119.6(3) no C15 . C20 . C19 . 121.5(5) yes C15 . C20 . H16 . 118.9(3) no C19 . C20 . H16 . 119.6(3) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C7 . O2 . C1 . O1 . 0.7(2) yes C7 . O2 . C1 . C2 . -176.7(1) yes C1 . O2 . C7 . C9 . -162.2(1) yes C8 . O4 . C6 . O3 . -0.4(1) yes C8 . O4 . C6 . C5 . 179.6(8) yes C6 . O4 . C8 . C15 . -171.6(8) yes O1 . C1 . C2 . C3 . 8.8(2) yes O2 . C1 . C2 . C3 . -173.9(9) yes C1 . C2 . C3 . C4 . 179.3(1) yes C2 . C3 . C4 . C5 . 175.0(1) yes C3 . C4 . C5 . C6 . 5.1(2) yes C4 . C5 . C6 . O3 . 6.4(2) yes C4 . C5 . C6 . O4 . -173.6(1) yes O2 . C7 . C9 . C10 . -134.0(8) yes O2 . C7 . C9 . C14 . 46.7(1) yes O4 . C8 . C15 . C16 . -139.6(7) yes O4 . C8 . C15 . C20 . 43.3(9) yes C7 . C9 . C10 . C11 . -176.5(8) yes C14 . C9 . C10 . C11 . 2.8(1) yes C7 . C9 . C14 . C13 . 177.4(9) yes C10 . C9 . C14 . C13 . -1.9(1) yes C9 . C10 . C11 . C12 . -2.8(1) yes C10 . C11 . C12 . O5 . -178.3(8) yes C10 . C11 . C12 . C13 . 1.8(1) yes O5 . C12 . C13 . C14 . 179.1(1) yes C11 . C12 . C13 . C14 . -1.0(1) yes C12 . C13 . C14 . C9 . 1.1(1) yes C8 . C15 . C16 . C17 . -174.7(7) yes C20 . C15 . C16 . C17 . 2.5(1) yes C8 . C15 . C20 . C19 . 174.2(8) yes C16 . C15 . C20 . C19 . -3.0(1) yes C15 . C16 . C17 . C18 . -1.1(1) yes C16 . C17 . C18 . O6 . 179.8(8) yes C16 . C17 . C18 . C19 . -0.1(1) yes O6 . C18 . C19 . C20 . 179.8(9) yes C17 . C18 . C19 . C20 . -0.3(1) yes C18 . C19 . C20 . C15 . 1.9(1) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_site_symmetry_1 _geom_contact_atom_site_label_2 _geom_contact_site_symmetry_2 _geom_contact_distance _geom_contact_publ_flag O1 . O2 . 2.264(6) yes O1 . O3 1_455 3.493(7) yes O1 . C1 . 1.216(11) yes O1 . C2 . 2.344(12) yes O1 . C3 . 2.817(13) yes O1 . C7 . 2.622(8) yes O1 . C8 2_456 3.369(9) yes O1 . C10 1_655 3.422(8) yes O1 . C17 2_556 3.374(9) yes O1 . H1 . 3.176(12) no O1 . H2 . 2.43(6) no O1 . H5 . 2.375(8) no O1 . H6 . 2.784(8) no O1 . H7 1_455 3.02(6) no O1 . H8 2_456 2.44(5) no O1 . H9 1_655 2.63(5) no O1 . H13 2_556 3.589(8) no O1 . H14 2_556 2.60(7) no O2 . O3 1_455 3.333(7) yes O2 . C1 . 1.363(8) yes O2 . C2 . 2.283(9) yes O2 . C7 . 1.434(8) yes O2 . C9 . 2.383(7) yes O2 . C10 . 3.538(7) yes O2 . C14 . 2.864(8) yes O2 . H1 . 2.44(1) no O2 . H1 2_366 3.059(11) no O2 . H4 2_466 3.552(9) no O2 . H5 . 1.964(9) no O2 . H6 . 1.972(8) no O2 . H10 1_655 3.555(7) no O2 . H12 . 2.63(6) no O3 . O4 . 2.224(6) yes O3 . C1 1_655 3.297(8) yes O3 . C3 . 2.985(11) yes O3 . C4 . 3.008(12) yes O3 . C5 . 2.39(1) yes O3 . C6 . 1.183(8) yes O3 . C7 1_655 3.575(9) yes O3 . C8 . 2.619(7) yes O3 . C8 2_556 3.224(8) yes O3 . C16 2_556 3.472(8) yes O3 . H2 . 2.35(6) no O3 . H4 . 3.162(11) no O3 . H6 1_655 2.931(9) no O3 . H7 . 2.82(6) no O3 . H7 2_556 2.80(6) no O3 . H8 . 2.56(4) no O3 . H8 2_556 3.02(5) no O3 . H13 1_455 2.970(7) no O3 . H13 2_556 2.966(8) no O4 . C2 1_655 3.576(8) yes O4 . C4 . 3.534(8) yes O4 . C5 . 2.295(8) yes O4 . C6 . 1.324(7) yes O4 . C8 . 1.467(7) yes O4 . C15 . 2.421(6) yes O4 . C16 . 3.595(7) yes O4 . C20 . 2.900(7) yes O4 . H4 . 2.361(8) no O4 . H7 . 2.21(6) no O4 . H8 . 1.93(5) no O4 . H11 2_466 3.442(8) no O4 . H12 2_466 3.00(7) no O4 . H14 1_455 3.29(6) no O4 . H16 . 2.645(7) no O5 . C11 . 2.51(1) yes O5 . C12 . 1.522(9) yes O5 . C13 . 2.524(11) yes O5 . H4 2_366 3.006(11) no O5 . H10 . 2.65(1) no O5 . H11 . 2.671(11) no O5 . H11 2_265 3.584(11) no O6 . C17 . 2.542(9) yes O6 . C18 . 1.530(9) yes O6 . C19 . 2.55(1) yes O6 . H5 1_756 3.527(11) no O6 . H9 2_456 3.43(5) no O6 . H10 1_856 3.43(1) no O6 . H14 . 2.75(6) no O6 . H15 . 2.698(11) no O6 . H16 1_655 3.525(11) no C1 . C2 . 1.409(12) yes C1 . C3 . 2.467(14) yes C1 . C6 1_455 3.560(9) yes C1 . C7 . 2.35(1) yes C1 . H1 . 2.072(14) no C1 . H2 . 2.60(6) no C1 . H5 . 2.458(11) no C1 . H6 . 2.68(1) no C1 . H7 1_455 3.16(6) no C1 . H8 2_456 3.34(5) no C1 . H9 1_655 3.13(5) no C2 . C3 . 1.499(13) yes C2 . C4 . 2.467(11) yes C2 . C4 2_466 3.498(11) yes C2 . C6 1_455 3.592(9) yes C2 . C7 . 3.591(11) yes C2 . H1 . 0.94998(8) no C2 . H2 . 2.22(6) no C2 . H3 . 2.579(13) no C2 . H3 2_466 3.138(11) no C2 . H7 1_455 3.04(6) no C3 . C4 . 1.333(12) yes C3 . C5 . 2.321(14) yes C3 . C6 . 3.009(13) yes C3 . H1 . 2.162(12) no C3 . H2 . 1.13(6) no C3 . H3 . 1.959(13) no C3 . H3 2_466 3.44(1) no C3 . H4 . 3.131(14) no C3 . H7 1_455 2.81(6) no C3 . H13 1_455 3.45(1) no C4 . C5 . 1.28(1) yes C4 . C6 . 2.51(1) yes C4 . H1 . 2.72(1) no C4 . H1 2_466 3.196(11) no C4 . H2 . 2.18(7) no C4 . H3 . 0.94998(9) no C4 . H4 . 1.888(11) no C4 . H7 1_455 3.55(6) no C5 . C6 . 1.49(1) yes C5 . C12 2_366 3.59(1) yes C5 . H1 2_466 3.461(9) no C5 . H2 . 2.71(6) no C5 . H3 . 1.910(11) no C5 . H4 . 0.95001(8) no C5 . H12 2_466 3.05(7) no C5 . H13 1_455 3.40(1) no C6 . C8 . 2.339(8) yes C6 . C16 1_455 3.598(8) yes C6 . H1 1_655 3.588(9) no C6 . H2 . 2.80(6) no C6 . H3 . 3.328(11) no C6 . H4 . 2.080(11) no C6 . H7 . 2.80(6) no C6 . H8 . 2.51(5) no C6 . H12 2_466 3.51(7) no C6 . H13 1_455 3.051(8) no C6 . H14 1_455 3.55(6) no C7 . C9 . 1.482(8) yes C7 . C10 . 2.476(8) yes C7 . C14 . 2.500(9) yes C7 . H2 1_455 3.59(6) no C7 . H5 . 0.94999(5) no C7 . H6 . 0.95005(6) no C7 . H9 . 2.79(5) no C7 . H10 1_655 3.52(1) no C7 . H12 . 2.82(7) no C8 . C15 . 1.509(7) yes C8 . C16 . 2.481(8) yes C8 . C20 . 2.540(8) yes C8 . H7 . 1.17(6) no C8 . H7 2_556 3.49(6) no C8 . H8 . 0.96(5) no C8 . H8 2_556 3.54(5) no C8 . H13 . 2.614(8) no C8 . H14 1_455 3.45(6) no C8 . H16 . 2.697(8) no C9 . C10 . 1.379(8) yes C9 . C11 . 2.408(8) yes C9 . C12 . 2.804(8) yes C9 . C13 . 2.414(8) yes C9 . C14 . 1.394(8) yes C9 . H3 2_366 3.164(12) no C9 . H5 . 2.000(8) no C9 . H6 . 2.013(9) no C9 . H9 . 2.18(5) no C9 . H10 . 3.260(8) no C9 . H11 . 3.267(8) no C9 . H12 . 2.19(7) no C10 . C11 . 1.399(8) yes C10 . C12 . 2.423(8) yes C10 . C13 . 2.754(8) yes C10 . C14 . 2.393(8) yes C10 . H3 2_366 3.107(13) no C10 . H5 . 2.994(8) no C10 . H6 . 2.519(8) no C10 . H9 . 1.05(5) no C10 . H10 . 2.042(8) no C10 . H12 . 3.36(7) no C10 . H15 1_354 3.306(8) no C11 . C12 . 1.387(9) yes C11 . C13 . 2.361(9) yes C11 . C14 . 2.766(9) yes C11 . H3 2_366 3.092(13) no C11 . H4 2_366 3.157(11) no C11 . H9 . 2.04(5) no C11 . H10 . 0.950 no C11 . H11 . 3.219(9) no C11 . H15 1_354 2.912(8) no C12 . C13 . 1.359(9) yes C12 . C14 . 2.418(9) yes C12 . H3 2_366 3.092(12) no C12 . H4 2_366 2.98(1) no C12 . H9 . 3.31(5) no C12 . H10 . 2.032(9) no C12 . H11 . 2.00(1) no C12 . H12 . 3.31(7) no C12 . H15 1_354 3.073(9) no C13 . C14 . 1.407(9) yes C13 . H3 2_366 3.110(11) no C13 . H10 . 3.218(9) no C13 . H11 . 0.94996(7) no C13 . H12 . 2.10(7) no C13 . H15 1_354 3.52(1) no C14 . H3 2_366 3.146(12) no C14 . H4 2_466 3.355(11) no C14 . H5 . 2.802(9) no C14 . H6 . 3.264(9) no C14 . H9 . 3.39(5) no C14 . H10 1_655 3.438(9) no C14 . H11 . 2.044(9) no C14 . H12 . 1.09(7) no C15 . C16 . 1.377(8) yes C15 . C17 . 2.417(8) yes C15 . C18 . 2.806(8) yes C15 . C19 . 2.396(8) yes C15 . C20 . 1.380(8) yes C15 . H6 2_456 3.111(8) no C15 . H7 . 2.14(6) no C15 . H8 . 1.95(5) no C15 . H11 2_466 3.352(8) no C15 . H13 . 2.022(8) no C15 . H14 . 3.25(7) no C15 . H15 . 3.247(8) no C15 . H16 . 2.019(8) no C16 . C17 . 1.401(8) yes C16 . C18 . 2.414(9) yes C16 . C19 . 2.750(8) yes C16 . C20 . 2.369(8) yes C16 . H2 2_556 3.51(7) no C16 . H6 2_456 2.965(9) no C16 . H7 . 2.51(6) no C16 . H8 . 2.96(5) no C16 . H9 2_456 3.57(5) no C16 . H13 . 0.94998(6) no C16 . H14 . 2.01(6) no C16 . H16 . 3.224(8) no C17 . C18 . 1.384(9) yes C17 . C19 . 2.393(9) yes C17 . C20 . 2.756(8) yes C17 . H6 2_456 3.246(9) no C17 . H9 2_456 2.86(5) no C17 . H13 . 2.043(8) no C17 . H14 . 0.95(6) no C17 . H15 . 3.252(9) no C17 . H16 1_655 3.360(9) no C18 . C19 . 1.406(9) yes C18 . C20 . 2.410(8) yes C18 . H9 2_456 3.17(5) no C18 . H13 . 3.266(9) no C18 . H14 . 2.06(6) no C18 . H15 . 2.049(9) no C18 . H16 . 3.266(8) no C19 . C20 . 1.366(8) yes C19 . H11 2_466 3.395(9) no C19 . H14 . 3.27(6) no C19 . H15 . 0.95002(6) no C19 . H16 . 2.013(9) no C20 . H5 2_456 3.563(9) no C20 . H6 2_456 3.532(9) no C20 . H7 . 3.43(6) no C20 . H8 . 2.72(5) no C20 . H11 2_466 2.999(9) no C20 . H13 . 3.228(8) no C20 . H14 1_455 3.39(6) no C20 . H15 . 2.013(8) no C20 . H16 . 0.950 no H1 . H1 2_366 3.129(17) no H1 . H2 . 3.08(6) no H1 . H3 . 2.478(11) no H1 . H3 2_466 3.102(11) no H1 . H4 2_466 3.595(9) no H1 . H12 2_366 3.19(6) no H2 . H3 . 2.99(7) no H2 . H6 1_655 2.89(6) no H2 . H7 1_455 2.74(8) no H2 . H9 1_655 3.19(7) no H2 . H13 1_455 3.16(6) no H2 . H13 2_556 3.00(7) no H2 . H14 2_556 3.59(9) no H3 . H3 2_466 3.592(16) no H3 . H4 . 2.12(1) no H3 . H12 2_366 3.41(6) no H4 . H10 2_366 3.224(11) no H4 . H12 2_466 2.28(7) no H5 . H6 . 1.551 no H5 . H9 . 3.28(5) no H5 . H9 1_655 3.41(5) no H5 . H10 1_655 2.90(1) no H5 . H12 . 3.09(7) no H6 . H8 2_456 3.27(4) no H6 . H9 . 2.46(5) no H6 . H13 2_456 3.239(9) no H7 . H7 2_556 3.47(12) no H7 . H8 . 1.86(7) no H7 . H8 2_556 2.92(8) no H7 . H13 . 2.21(6) no H8 . H8 2_556 3.45(9) no H8 . H13 1_455 3.56(5) no H8 . H13 . 3.15(5) no H8 . H14 1_455 2.79(7) no H8 . H16 . 2.74(5) no H9 . H10 . 2.27(5) no H9 . H14 2_456 2.69(8) no H10 . H12 1_455 3.12(6) no H10 . H15 1_354 3.122(9) no H11 . H12 . 2.34(6) no H11 . H16 2_466 3.049(9) no H13 . H14 . 2.29(6) no H14 . H16 1_655 2.71(6) no H15 . H16 . 2.305(8) no #===END data_poly(1) #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C22 H22 O6 ' _chemical_formula_moiety 'C22 H22 O6 ' _chemical_formula_weight 382.41 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' 'x+1/2,y+1/2,z' '-x+1/2,-y+1/2,-z' '-x,y,-z+1/2' 'x,-y,z+1/2' '-x+1/2,y+1/2,-z+1/2' 'x+1/2,-y+1/2,z+1/2' #------------------------------------------------------------------------------ _cell_length_a 35.117(4) _cell_length_b 5.7980(6) _cell_length_c 9.436(1) _cell_angle_alpha 90 _cell_angle_beta 99.321(2) _cell_angle_gamma 90 _cell_volume 1895.9(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7037 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 296.1 #------------------------------------------------------------------------------ _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 6714 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_theta_max 27.46 _diffrn_measured_fraction_theta_max 0.9796 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.9796 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.0 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 2355 _reflns_number_gt 1612 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.0710 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1620 _refine_ls_number_parameters 171 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.005Fo^2^ + 1.000\s^2^(Fo)]' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.21 _refine_diff_density_min -0.22 _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' 0.006 0.003 ; 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' 0.017 0.010 ; 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 O1 O 0.03855(5) 0.4788(3) 0.6851(2) 0.0674(5) Uani 1.00 1 d . . . O2 O 0.07108(4) 0.2433(2) 0.8470(1) 0.0381(3) Uani 1.00 1 d . . . O3 O 0.21546(4) 0.1911(3) 1.3456(1) 0.0497(4) Uani 1.00 1 d . . . C1 C 0.04262(5) 0.2918(3) 0.7402(2) 0.0326(4) Uani 1.00 1 d . . . C2 C 0.01630(5) 0.0862(3) 0.7015(1) 0.0274(4) Uani 1.00 1 d . . . C3 C 0.00027(5) 0.0910(3) 0.5419(1) 0.0289(4) Uani 1.00 1 d . . . C4 C 0.09421(6) 0.4397(4) 0.9033(2) 0.0439(5) Uani 1.00 1 d . . . C5 C 0.12521(5) 0.3588(3) 1.0211(2) 0.0346(4) Uani 1.00 1 d . . . C6 C 0.15766(6) 0.4985(3) 1.0552(2) 0.0402(5) Uani 1.00 1 d . . . C7 C 0.18688(5) 0.4385(3) 1.1637(2) 0.0409(5) Uani 1.00 1 d . . . C8 C 0.18452(5) 0.2357(3) 1.2417(2) 0.0356(4) Uani 1.00 1 d . . . C9 C 0.15229(5) 0.0958(3) 1.2112(2) 0.0393(5) Uani 1.00 1 d . . . C10 C 0.12291(5) 0.1595(3) 1.1006(2) 0.0400(5) Uani 1.00 1 d . . . C11 C 0.21500(7) -0.0151(4) 1.4284(3) 0.0555(6) Uani 1.00 1 d . . . H1 H 0.0308(5) -0.055(3) 0.724(2) 0.024(4) Uiso 1.00 1 c . . . H2 H -0.0097(5) 0.236(4) 0.508(2) 0.032(5) Uiso 1.00 1 c . . . H3 H 0.0763(8) 0.547(5) 0.947(2) 0.069(8) Uiso 1.00 1 c . . . H4 H 0.1053(8) 0.507(5) 0.825(3) 0.067(7) Uiso 1.00 1 c . . . H5 H 0.1590(7) 0.637(4) 1.000(2) 0.048(6) Uiso 1.00 1 c . . . H6 H 0.2081(7) 0.537(4) 1.185(2) 0.048(6) Uiso 1.00 1 c . . . H7 H 0.1501(7) -0.041(4) 1.262(3) 0.058(7) Uiso 1.00 1 c . . . H8 H 0.1012(7) 0.066(4) 1.084(2) 0.051(6) Uiso 1.00 1 c . . . H9 H 0.2376(9) -0.008(5) 1.500(3) 0.080(8) Uiso 1.00 1 c . . . H10 H 0.190(1) -0.029(6) 1.474(3) 0.09(1) Uiso 1.00 1 c . . . H11 H 0.2160(9) -0.161(5) 1.362(3) 0.10(1) Uiso 1.00 1 c . . . 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 O1 0.078(1) 0.0453(9) 0.065(1) -0.0178(8) -0.0318(8) 0.0252(7) O2 0.0378(7) 0.0390(7) 0.0328(6) -0.0043(5) -0.0080(5) 0.0026(5) O3 0.0401(7) 0.0589(9) 0.0448(8) -0.0025(6) -0.0088(6) 0.0063(6) C1 0.0379(9) 0.0372(9) 0.0216(7) -0.0008(7) 0.0017(6) 0.0042(6) C2 0.0358(8) 0.0291(8) 0.0161(6) 0.0043(6) 0.0002(6) 0.0006(5) C3 0.0357(8) 0.0335(8) 0.0163(6) 0.0052(7) 0.0004(6) 0.0032(6) C4 0.045(1) 0.042(1) 0.0400(9) -0.0102(8) -0.0072(8) 0.0065(8) C5 0.0339(9) 0.0402(9) 0.0285(7) -0.0048(7) 0.0017(6) -0.0018(7) C6 0.046(1) 0.039(1) 0.0345(8) -0.0103(8) 0.0018(7) 0.0030(7) C7 0.0380(9) 0.045(1) 0.0378(9) -0.0132(8) 0.0006(7) -0.0031(7) C8 0.0330(9) 0.043(1) 0.0292(8) 0.0004(7) 0.0020(7) -0.0046(7) C9 0.0404(9) 0.041(1) 0.0351(9) -0.0043(8) 0.0009(7) 0.0063(7) C10 0.0339(9) 0.044(1) 0.0393(9) -0.0104(8) -0.0014(7) 0.0025(7) C11 0.050(1) 0.062(1) 0.050(1) 0.008(1) -0.007(1) 0.010(1) #============================================================================== _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'CrystalStructure' _computing_structure_solution 'SIR92' _computing_structure_refinement 'CRYSTALS' _computing_publication_material 'CrystalStructure Ver. 2.00' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.201(2) yes O2 . C1 . 1.3297(19) yes O2 . C4 . 1.449(2) yes O3 . C8 . 1.365(2) yes O3 . C11 . 1.430(3) yes C1 . C2 . 1.517(2) yes C2 . C3 . 1.5204(17) yes C2 . H1 . 0.968(18) no C3 . H2 . 0.94(2) no C4 . C5 . 1.500(2) yes C4 . H3 . 1.02(3) no C4 . H4 . 0.97(3) no C5 . C6 . 1.393(2) yes C5 . C10 . 1.388(3) yes C6 . C7 . 1.372(3) yes C6 . H5 . 0.96(2) no C7 . C8 . 1.397(3) yes C7 . H6 . 0.93(2) no C8 . C9 . 1.384(3) yes C9 . C10 . 1.393(2) yes C9 . H7 . 0.94(3) no C10 . H8 . 0.93(2) no C11 . H9 . 0.96(3) no C11 . H10 . 1.05(3) no C11 . H11 . 1.06(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O2 . C4 . 114.79(13) yes C8 . O3 . C11 . 118.20(16) yes O1 . C1 . O2 . 122.79(16) yes O1 . C1 . C2 . 125.47(15) yes O2 . C1 . C2 . 111.72(13) yes C1 . C2 . C3 . 109.73(12) yes C1 . C2 . H1 . 109.4(10) no C3 . C2 . H1 . 109.5(10) no C2 . C3 . H2 . 114.3(11) no O2 . C4 . C5 . 108.79(15) yes O2 . C4 . H3 . 106.4(15) no C5 . C4 . H3 . 108.1(13) no O2 . C4 . H4 . 107.8(16) no C5 . C4 . H4 . 110.9(16) no H3 . C4 . H4 . 114.6(22) no C4 . C5 . C6 . 117.26(16) yes C4 . C5 . C10 . 124.24(16) yes C6 . C5 . C10 . 118.46(16) yes C5 . C6 . C7 . 120.67(17) yes C5 . C6 . H5 . 118.1(14) no C7 . C6 . H5 . 121.3(14) no C6 . C7 . C8 . 120.38(16) yes C6 . C7 . H6 . 118.8(13) no C8 . C7 . H6 . 120.8(13) no O3 . C8 . C7 . 115.43(16) yes O3 . C8 . C9 . 124.54(17) yes C7 . C8 . C9 . 120.03(15) yes C8 . C9 . C10 . 118.77(17) yes C8 . C9 . H7 . 121.5(15) no C10 . C9 . H7 . 119.7(15) no C5 . C10 . C9 . 121.67(17) yes C5 . C10 . H8 . 121.0(14) no C9 . C10 . H8 . 117.3(14) no O3 . C11 . H9 . 105.6(18) no O3 . C11 . H10 . 111.9(17) no H9 . C11 . H10 . 111.8(24) no O3 . C11 . H11 . 109.7(17) no H9 . C11 . H11 . 110.6(24) no H10 . C11 . H11 . 107.3(24) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C4 . O2 . C1 . O1 . 6.8(4) yes C4 . O2 . C1 . C2 . -171.8(2) yes C1 . O2 . C4 . C5 . -179.4(2) yes C11 . O3 . C8 . C7 . -179.4(3) yes C11 . O3 . C8 . C9 . 0.6(4) yes O1 . C1 . C2 . C3 . 33.3(3) yes O2 . C1 . C2 . C3 . -148.1(2) yes O2 . C4 . C5 . C6 . 158.6(2) yes O2 . C4 . C5 . C10 . -23.7(3) yes C4 . C5 . C6 . C7 . 178.7(2) yes C10 . C5 . C6 . C7 . 0.9(4) yes C4 . C5 . C10 . C9 . -178.5(2) yes C6 . C5 . C10 . C9 . -0.9(4) yes C5 . C6 . C7 . C8 . 0.1(4) yes C6 . C7 . C8 . O3 . 179.0(2) yes C6 . C7 . C8 . C9 . -1.0(4) yes O3 . C8 . C9 . C10 . -179.0(2) yes C7 . C8 . C9 . C10 . 1.0(4) yes C8 . C9 . C10 . C5 . -0.1(4) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_site_symmetry_1 _geom_contact_atom_site_label_2 _geom_contact_site_symmetry_2 _geom_contact_distance _geom_contact_publ_flag O1 . O1 5_556 3.147(4) yes O1 . O2 . 2.2225(17) yes O1 . C1 . 1.201(2) yes O1 . C1 5_556 3.232(3) yes O1 . C2 . 2.420(2) yes O1 . C2 5_556 3.272(2) yes O1 . C3 . 2.846(2) yes O1 . C3 2_566 3.424(2) yes O1 . C4 . 2.609(2) yes O1 . C4 6_564 3.578(3) yes O1 . H1 . 3.133(18) no O1 . H1 1_565 2.749(18) no O1 . H2 . 2.595(18) no O1 . H2 2_566 2.546(19) no O1 . H2 5_556 3.517(19) no O1 . H3 . 2.64(2) no O1 . H3 6_564 2.79(3) no O1 . H4 . 2.50(3) no O2 . C1 . 1.3297(19) yes O2 . C2 . 2.3582(18) yes O2 . C2 5_556 3.162(2) yes O2 . C3 . 3.5967(18) yes O2 . C3 5_556 3.001(2) yes O2 . C4 . 1.449(2) yes O2 . C5 . 2.3977(19) yes O2 . C10 . 2.804(2) yes O2 . H1 . 2.408(17) no O2 . H2 5_556 2.737(19) no O2 . H3 . 1.99(3) no O2 . H4 . 1.97(3) no O2 . H7 6_554 3.23(2) no O2 . H8 . 2.53(2) no O2 . H8 6_554 3.37(2) no O3 . O3 4_558 3.543(3) yes O3 . C6 6_565 3.546(2) yes O3 . C7 . 2.335(2) yes O3 . C8 . 1.365(2) yes O3 . C9 . 2.434(2) yes O3 . C11 . 1.430(3) yes O3 . C11 4_558 3.515(3) yes O3 . H5 6_565 2.83(2) no O3 . H6 . 2.50(2) no O3 . H6 7_547 2.89(2) no O3 . H7 . 2.67(2) no O3 . H9 . 1.92(3) no O3 . H9 4_558 2.73(3) no O3 . H10 . 2.06(3) no O3 . H11 . 2.05(3) no O3 . H11 7_557 3.45(3) no C1 . C1 5_556 3.029(4) yes C1 . C2 . 1.517(2) yes C1 . C2 5_556 2.525(2) yes C1 . C3 . 2.484(2) yes C1 . C3 5_556 2.976(2) yes C1 . C4 . 2.342(2) yes C1 . H1 . 2.053(18) no C1 . H1 5_556 3.327(19) no C1 . H2 . 2.642(18) no C1 . H2 5_556 2.828(18) no C1 . H3 . 2.58(2) no C1 . H3 6_564 3.31(3) no C1 . H4 . 2.54(3) no C1 . H8 6_554 3.42(2) no C2 . C2 5_556 1.578(3) yes C2 . C3 . 1.5204(17) yes C2 . C3 2_556 2.497(2) yes C2 . C3 5_556 2.581(2) yes C2 . C3 6_555 3.5032(19) yes C2 . H1 . 0.968(18) no C2 . H1 5_556 2.064(18) no C2 . H2 . 2.094(18) no C2 . H2 2_556 2.699(19) no C2 . H2 5_556 2.923(18) no C2 . H8 6_554 3.46(2) no C3 . C3 2_556 1.316(3) yes C3 . H1 . 2.057(17) no C3 . H1 2_556 2.581(16) no C3 . H1 5_556 2.746(17) no C3 . H1 6_554 3.346(17) no C3 . H2 . 0.94(2) no C3 . H2 2_556 1.99(2) no C3 . H8 5_556 3.57(2) no C4 . C5 . 1.500(2) yes C4 . C6 . 2.470(2) yes C4 . C10 . 2.553(3) yes C4 . H2 5_556 3.425(19) no C4 . H3 . 1.02(3) no C4 . H4 . 0.97(3) no C4 . H5 . 2.58(2) no C4 . H7 6_554 3.44(3) no C4 . H8 . 2.74(2) no C5 . C6 . 1.393(2) yes C5 . C7 . 2.402(2) yes C5 . C8 . 2.788(2) yes C5 . C9 . 2.428(2) yes C5 . C10 . 1.388(3) yes C5 . H3 . 2.06(3) no C5 . H4 . 2.06(3) no C5 . H4 6_565 3.16(3) no C5 . H5 . 2.03(2) no C5 . H6 . 3.24(2) no C5 . H7 . 3.27(3) no C5 . H7 6_554 3.29(3) no C5 . H8 . 2.03(2) no C5 . H10 6_554 3.06(3) no C6 . C7 . 1.372(3) yes C6 . C8 . 2.402(2) yes C6 . C8 6_564 3.595(2) yes C6 . C9 . 2.783(3) yes C6 . C10 . 2.389(3) yes C6 . H3 . 2.89(3) no C6 . H4 . 2.61(3) no C6 . H4 6_565 3.37(3) no C6 . H5 . 0.96(2) no C6 . H6 . 2.00(2) no C6 . H7 1_565 3.34(2) no C6 . H8 . 3.23(2) no C6 . H10 6_554 3.09(3) no C6 . H10 6_564 3.40(3) no C6 . H11 6_554 3.55(3) no C7 . C8 . 1.397(3) yes C7 . C9 . 2.409(3) yes C7 . C10 . 2.754(2) yes C7 . C11 6_554 3.555(3) yes C7 . H4 6_565 3.47(3) no C7 . H5 . 2.04(2) no C7 . H5 6_565 3.50(2) no C7 . H6 . 0.93(2) no C7 . H7 . 3.26(3) no C7 . H7 1_565 3.47(2) no C7 . H9 7_557 3.29(3) no C7 . H9 6_554 3.56(3) no C7 . H10 6_554 2.99(3) no C7 . H11 1_565 3.05(3) no C7 . H11 7_557 3.51(3) no C7 . H11 6_554 3.56(3) no C8 . C9 . 1.384(3) yes C8 . C10 . 2.390(2) yes C8 . C11 . 2.399(3) yes C8 . C11 6_554 3.542(3) yes C8 . H4 6_565 3.36(3) no C8 . H5 . 3.28(2) no C8 . H5 6_565 2.83(2) no C8 . H6 . 2.04(2) no C8 . H7 . 2.04(3) no C8 . H8 . 3.21(2) no C8 . H9 . 3.15(3) no C8 . H9 6_554 3.43(3) no C8 . H10 . 2.66(3) no C8 . H10 6_554 2.83(3) no C8 . H11 . 2.72(3) no C9 . C10 . 1.393(2) yes C9 . C11 . 2.828(3) yes C9 . H4 6_565 3.13(3) no C9 . H5 1_545 3.35(2) no C9 . H5 6_565 3.11(2) no C9 . H6 . 3.26(2) no C9 . H7 . 0.94(3) no C9 . H8 . 2.00(2) no C9 . H10 . 2.71(3) no C9 . H10 6_554 2.80(3) no C9 . H11 . 2.86(3) no C10 . H3 . 3.01(3) no C10 . H4 . 3.27(3) no C10 . H4 6_565 3.01(3) no C10 . H5 1_545 3.47(2) no C10 . H5 . 3.25(2) no C10 . H7 . 2.03(3) no C10 . H7 6_554 3.55(2) no C10 . H8 . 0.93(2) no C10 . H10 6_554 2.91(3) no C11 . H5 6_565 3.09(2) no C11 . H6 1_545 3.45(2) no C11 . H6 7_547 3.08(2) no C11 . H7 . 2.55(2) no C11 . H9 . 0.96(3) no C11 . H9 4_548 3.24(3) no C11 . H9 4_558 3.47(3) no C11 . H10 . 1.05(3) no C11 . H11 . 1.06(3) no C11 . H11 4_548 3.43(3) no H1 . H1 5_556 2.29(4) no H1 . H2 . 2.84(3) no H1 . H2 2_556 2.43(2) no H1 . H2 5_556 3.22(3) no H1 . H2 6_555 3.39(2) no H1 . H3 1_545 3.35(3) no H1 . H8 6_554 2.99(3) no H2 . H2 2_556 2.82(4) no H2 . H2 2_566 3.15(4) no H2 . H3 5_556 3.04(3) no H2 . H3 6_564 3.40(3) no H2 . H8 5_556 3.34(3) no H3 . H4 . 1.67(3) no H3 . H4 6_565 3.56(3) no H3 . H5 . 2.91(3) no H3 . H8 . 3.14(4) no H3 . H8 1_565 3.34(4) no H4 . H5 . 2.42(3) no H4 . H7 6_554 3.23(4) no H4 . H7 6_564 3.57(4) no H4 . H8 . 3.55(4) no H4 . H8 6_564 3.35(4) no H5 . H6 . 2.32(3) no H5 . H7 1_565 3.15(3) no H5 . H7 6_564 3.23(3) no H5 . H8 1_565 3.38(3) no H5 . H9 6_564 3.50(4) no H5 . H10 6_564 2.55(4) no H6 . H7 1_565 3.34(3) no H6 . H9 4_558 3.26(4) no H6 . H9 7_557 2.80(4) no H6 . H9 6_564 3.49(4) no H6 . H10 6_554 3.56(4) no H6 . H10 6_564 3.48(4) no H6 . H11 1_565 2.40(4) no H6 . H11 7_557 3.00(4) no H7 . H8 . 2.28(3) no H7 . H9 . 3.51(4) no H7 . H10 . 2.25(4) no H7 . H10 6_554 3.28(4) no H7 . H11 . 2.45(4) no H8 . H10 6_554 3.44(4) no H9 . H9 4_548 2.94(6) no H9 . H9 4_558 3.11(6) no H9 . H10 . 1.66(4) no H9 . H11 . 1.66(4) no H9 . H11 4_548 2.71(4) no H10 . H11 . 1.69(4) no H11 . H11 4_548 3.40(6) no #===END