 
data_01sot039
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H20 O4' 
_chemical_formula_weight          264.31 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    P2(1)2(1)2(1) 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 
_cell_length_a                    7.5556(3) 
_cell_length_b                    8.0446(3) 
_cell_length_c                    22.9549(8) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1395.24(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     3618 
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       26.02 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.25 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.258 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              568 
_exptl_absorpt_coefficient_mu     0.090 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9778 
_exptl_absorpt_correction_T_max   0.9928 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans' 
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             3873 
_diffrn_reflns_av_R_equivalents   0.0609 
_diffrn_reflns_av_sigmaI/netI     0.0650 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        7 
_diffrn_reflns_limit_l_min        -25 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          3.23 
_diffrn_reflns_theta_max          23.25 
_reflns_number_total              1860 
_reflns_number_gt                 1668 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)' 
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'  
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'  
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0959P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.016(9) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1.9(17) 
_refine_ls_number_reflns          1860 
_refine_ls_number_parameters      175 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0565 
_refine_ls_R_factor_gt            0.0507 
_refine_ls_wR_factor_ref          0.1368 
_refine_ls_wR_factor_gt           0.1298 
_refine_ls_goodness_of_fit_ref    1.033 
_refine_ls_restrained_S_all       1.033 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.2736(4) 0.6913(4) 0.10427(12) 0.0370(7) Uani 1 1 d . . . 
C2 C 0.1755(4) 0.6411(4) 0.05535(12) 0.0438(7) Uani 1 1 d . . . 
H2 H 0.1459 0.5273 0.0503 0.053 Uiso 1 1 calc R . . 
C3 C 0.1218(4) 0.7566(5) 0.01454(13) 0.0513(8) Uani 1 1 d . . . 
H3 H 0.0549 0.7218 -0.0183 0.062 Uiso 1 1 calc R . . 
C4 C 0.1645(4) 0.9217(4) 0.02106(13) 0.0494(8) Uani 1 1 d . . . 
H4 H 0.1290 1.0000 -0.0076 0.059 Uiso 1 1 calc R . . 
C5 C 0.2593(4) 0.9740(4) 0.06941(12) 0.0454(7) Uani 1 1 d . . . 
H5 H 0.2872 1.0883 0.0741 0.055 Uiso 1 1 calc R . . 
C6 C 0.3131(4) 0.8598(4) 0.11070(12) 0.0396(7) Uani 1 1 d . . . 
H6 H 0.3776 0.8963 0.1438 0.048 Uiso 1 1 calc R . . 
C7 C 0.3336(4) 0.5615(4) 0.14589(12) 0.0375(6) Uani 1 1 d . . . 
C8 C 0.4678(4) 0.6064(3) 0.19284(11) 0.0377(7) Uani 1 1 d . . . 
H8 H 0.4362 0.7167 0.2100 0.045 Uiso 1 1 calc R . . 
C9 C 0.6510(4) 0.6181(4) 0.16362(12) 0.0390(7) Uani 1 1 d . . . 
H9 H 0.6576 0.7235 0.1406 0.047 Uiso 1 1 calc R . . 
C10 C 0.8070(4) 0.6119(4) 0.20643(14) 0.0459(8) Uani 1 1 d . . . 
H10A H 0.9069 0.6811 0.1926 0.055 Uiso 1 1 calc R . . 
H10B H 0.7711 0.6497 0.2457 0.055 Uiso 1 1 calc R . . 
C11 C 0.8556(4) 0.4280(4) 0.20649(13) 0.0441(7) Uani 1 1 d . . . 
H11A H 0.9823 0.4120 0.2158 0.053 Uiso 1 1 calc R . . 
H11B H 0.7830 0.3656 0.2350 0.053 Uiso 1 1 calc R . . 
C12 C 0.8153(4) 0.3735(4) 0.14472(12) 0.0389(7) Uani 1 1 d . . . 
H12 H 0.9219 0.3947 0.1200 0.047 Uiso 1 1 calc R . . 
C13 C 0.7572(4) 0.1959(4) 0.13576(11) 0.0400(7) Uani 1 1 d . . . 
C14 C 0.8904(4) 0.0761(4) 0.16310(15) 0.0518(8) Uani 1 1 d . . . 
H14A H 0.8509 -0.0386 0.1569 0.078 Uiso 1 1 calc R . . 
H14B H 0.8991 0.0981 0.2050 0.078 Uiso 1 1 calc R . . 
H14C H 1.0066 0.0919 0.1450 0.078 Uiso 1 1 calc R . . 
C15 C 0.7308(5) 0.1569(4) 0.07108(13) 0.0538(8) Uani 1 1 d . . . 
H15A H 0.6929 0.0411 0.0667 0.081 Uiso 1 1 calc R . . 
H15B H 0.8425 0.1739 0.0502 0.081 Uiso 1 1 calc R . . 
H15C H 0.6400 0.2308 0.0550 0.081 Uiso 1 1 calc R . . 
O1 O 0.2827(2) 0.4173(3) 0.14196(9) 0.0492(6) Uani 1 1 d . . . 
O2 O 0.4660(3) 0.4844(3) 0.23708(8) 0.0463(6) Uani 1 1 d . . . 
H2A H 0.4484 0.5301 0.2695 0.070 Uiso 1 1 calc R . . 
O3 O 0.6736(2) 0.4792(2) 0.12492(8) 0.0386(5) Uani 1 1 d . . . 
O4 O 0.5913(2) 0.1663(3) 0.16547(8) 0.0406(5) Uani 1 1 d . . . 
H4A H 0.5262 0.2504 0.1622 0.061 Uiso 1 1 calc R . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
C1 0.0293(14) 0.0461(16) 0.0356(15) -0.0020(12) 0.0015(10) 0.0000(12) 
C2 0.0359(13) 0.0545(17) 0.0409(16) -0.0037(15) -0.0020(12) -0.0031(15) 
C3 0.0435(18) 0.069(2) 0.0410(18) -0.0021(17) -0.0064(13) 0.0007(17) 
C4 0.0445(16) 0.061(2) 0.0430(16) 0.0074(15) -0.0002(14) 0.0063(16) 
C5 0.0383(15) 0.0486(17) 0.0494(16) 0.0004(14) 0.0024(13) 0.0037(14) 
C6 0.0355(15) 0.0466(16) 0.0366(15) -0.0023(13) -0.0006(11) 0.0042(13) 
C7 0.0300(13) 0.0413(16) 0.0412(15) -0.0030(12) 0.0063(12) 0.0009(13) 
C8 0.0419(15) 0.0405(16) 0.0308(14) -0.0040(12) -0.0010(11) 0.0053(13) 
C9 0.0383(14) 0.0392(15) 0.0394(15) 0.0006(13) -0.0048(12) -0.0035(13) 
C10 0.0411(17) 0.0439(17) 0.0528(18) 0.0005(14) -0.0145(13) -0.0031(14) 
C11 0.0362(16) 0.0457(16) 0.0505(17) 0.0031(14) -0.0098(12) -0.0042(13) 
C12 0.0290(13) 0.0436(16) 0.0439(15) 0.0050(13) 0.0035(11) 0.0024(12) 
C13 0.0408(15) 0.0442(16) 0.0350(14) 0.0023(13) 0.0046(13) -0.0009(13) 
C14 0.0496(18) 0.0453(17) 0.060(2) 0.0028(16) 0.0050(14) 0.0060(15) 
C15 0.0655(19) 0.0521(19) 0.0438(17) -0.0053(15) 0.0079(15) -0.0026(16) 
O1 0.0415(12) 0.0483(13) 0.0578(13) 0.0051(10) -0.0071(10) -0.0060(10) 
O2 0.0570(13) 0.0482(12) 0.0339(10) 0.0016(9) 0.0042(9) 0.0083(11) 
O3 0.0354(10) 0.0444(11) 0.0359(9) 0.0002(9) -0.0011(7) 0.0033(9) 
O4 0.0379(10) 0.0428(11) 0.0411(10) 0.0024(10) 0.0032(8) -0.0052(9) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 C6 1.396(4) . ? 
C1 C2 1.405(4) . ? 
C1 C7 1.486(4) . ? 
C2 C3 1.380(5) . ? 
C3 C4 1.375(5) . ? 
C4 C5 1.386(4) . ? 
C5 C6 1.381(4) . ? 
C7 O1 1.225(4) . ? 
C7 C8 1.523(4) . ? 
C8 O2 1.413(3) . ? 
C8 C9 1.541(4) . ? 
C9 O3 1.438(3) . ? 
C9 C10 1.536(4) . ? 
C10 C11 1.524(4) . ? 
C11 C12 1.515(4) . ? 
C12 O3 1.441(3) . ? 
C12 C13 1.509(4) . ? 
C13 O4 1.447(3) . ? 
C13 C14 1.528(4) . ? 
C13 C15 1.530(4) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C6 C1 C2 118.4(3) . . ? 
C6 C1 C7 123.3(2) . . ? 
C2 C1 C7 118.2(3) . . ? 
C3 C2 C1 120.3(3) . . ? 
C4 C3 C2 120.5(3) . . ? 
C3 C4 C5 120.1(3) . . ? 
C6 C5 C4 120.0(3) . . ? 
C5 C6 C1 120.7(3) . . ? 
O1 C7 C1 121.5(3) . . ? 
O1 C7 C8 119.1(3) . . ? 
C1 C7 C8 119.4(2) . . ? 
O2 C8 C7 109.7(2) . . ? 
O2 C8 C9 111.3(2) . . ? 
C7 C8 C9 107.7(2) . . ? 
O3 C9 C10 106.2(2) . . ? 
O3 C9 C8 109.1(2) . . ? 
C10 C9 C8 114.2(2) . . ? 
C11 C10 C9 102.5(2) . . ? 
C12 C11 C10 103.4(2) . . ? 
O3 C12 C13 107.4(2) . . ? 
O3 C12 C11 105.9(2) . . ? 
C13 C12 C11 117.4(2) . . ? 
O4 C13 C12 110.1(2) . . ? 
O4 C13 C14 105.8(2) . . ? 
C12 C13 C14 110.5(2) . . ? 
O4 C13 C15 108.1(2) . . ? 
C12 C13 C15 111.4(2) . . ? 
C14 C13 C15 110.8(3) . . ? 
C9 O3 C12 110.6(2) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O2 H2A O4  0.84 1.88 2.708(3) 170.2 3_655 
O4 H4A O3  0.84 2.32 2.755(3) 113.0 . 
O4 H4A O1  0.84 2.32 3.132(3) 161.2 . 
O4 H4A O2  0.84 2.59 3.185(3) 129.0 . 
 
_diffrn_measured_fraction_theta_max    0.976 
_diffrn_reflns_theta_full              23.25 
_diffrn_measured_fraction_theta_full   0.976 
_refine_diff_density_max    0.192 
_refine_diff_density_min   -0.239 
_refine_diff_density_rms    0.043 
