data_xl
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C17 H34 O4'
_chemical_formula_weight          302.44
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P21
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    5.524(4)
_cell_length_b                    8.048(5)
_cell_length_c                    20.295(12)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.180(14)
_cell_angle_gamma                 90.00
_cell_volume                      895.2(10)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used                2048
_cell_measurement_theta_min                  2.25
_cell_measurement_theta_max                 64.64
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colorless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.122
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              336
_exptl_absorpt_coefficient_mu     0.618
_exptl_absorpt_correction_type         'multi-scan'
_exptl_absorpt_correction_T_min            0.1337
_exptl_absorpt_correction_T_max            1.0000
_exptl_absorpt_process_details 
;  Shape and scale corrections using equivalent reflections.
   Shape function based on spherical harmonics.
   Highest even and odd order for spherical harmonics:  6  and  1
   Laue group:  2/m (b)
   Friedel opposites are not equivalent.
;
 
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54180 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'R-AXIS-CS3 6.X, c++'
_diffrn_measurement_method        '\w scans' 
_diffrn_reflns_number             8951
_diffrn_reflns_av_R_equivalents   0.1640
_diffrn_reflns_av_sigmaI/netI     0.0061
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          4.39
_diffrn_reflns_theta_max          71.19
_reflns_number_total              2294
_reflns_number_gt                 2089
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'TwinSolve'
_computing_cell_refinement        'TwinSolve'
_computing_data_reduction         'TwinSolve'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP-III for windows (Farrugia, 1997)'
_computing_publication_material   ?  
_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^)+(0.0982P)^2^+2.2284P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.5(7)
_refine_ls_number_reflns          2294
_refine_ls_number_parameters      196
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0975
_refine_ls_R_factor_gt            0.0882
_refine_ls_wR_factor_ref          0.2358
_refine_ls_wR_factor_gt           0.2253
_refine_ls_goodness_of_fit_ref    1.071
_refine_ls_restrained_S_all       1.071
_refine_ls_shift/su_max           0.016
_refine_ls_shift/su_mean          0.003
 
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 -0.0032(8) 0.4030(5) 0.05311(17) 0.0382(10) Uani 1 1 d . . .
O2 O 0.1766(8) 0.2724(5) 0.1434(2) 0.0399(10) Uani 1 1 d . . .
HO2 H 0.285(18) 0.220(13) 0.114(5) 0.10(3) Uiso 1 1 d . . .
O3 O -0.6053(8) 0.7902(5) 0.03412(18) 0.0358(10) Uani 1 1 d . . .
HO3 H -0.7238 0.8502 0.0237 0.054 Uiso 1 1 calc R . .
O4 O -0.5414(8) 1.1326(5) 0.0653(2) 0.0377(10) Uani 1 1 d . . .
HO4 H -0.6625 1.0869 0.0458 0.057 Uiso 1 1 calc R . .
C1 C 0.0061(11) 0.3705(7) 0.1116(3) 0.0344(13) Uani 1 1 d . . .
C2 C -0.1698(11) 0.4265(8) 0.1565(3) 0.0358(13) Uani 1 1 d . . .
H2A H -0.0793 0.4815 0.1944 0.043 Uiso 1 1 calc R . .
H2B H -0.2464 0.3291 0.1730 0.043 Uiso 1 1 calc R . .
C3 C -0.3699(12) 0.5436(7) 0.1263(3) 0.0352(13) Uani 1 1 d . . .
H3A H -0.4422 0.4988 0.0840 0.042 Uiso 1 1 calc R . .
H3B H -0.4966 0.5488 0.1553 0.042 Uiso 1 1 calc R . .
C4 C -0.2793(12) 0.7174(7) 0.1156(3) 0.0360(14) Uani 1 1 d . . .
H4A H -0.1727 0.7136 0.0811 0.043 Uiso 1 1 calc R . .
H4B H -0.1822 0.7539 0.1562 0.043 Uiso 1 1 calc R . .
C5 C -0.4769(12) 0.8455(7) 0.0963(3) 0.0329(13) Uani 1 1 d . . .
C6 C -0.3595(12) 1.0113(7) 0.0852(3) 0.0365(14) Uani 1 1 d . . .
H6A H -0.2622 1.0468 0.1258 0.044 Uiso 1 1 calc R . .
H6B H -0.2521 0.9999 0.0511 0.044 Uiso 1 1 calc R . .
C7 C -0.6628(11) 0.8570(7) 0.1455(3) 0.0322(13) Uani 1 1 d . . .
H7A H -0.7453 0.7506 0.1457 0.039 Uiso 1 1 calc R . .
H7B H -0.7843 0.9386 0.1287 0.039 Uiso 1 1 calc R . .
C8 C -0.5708(11) 0.9024(8) 0.2176(3) 0.0348(13) Uani 1 1 d . . .
H8A H -0.4521 0.8207 0.2361 0.042 Uiso 1 1 calc R . .
H8B H -0.4913 1.0100 0.2190 0.042 Uiso 1 1 calc R . .
C9 C -0.7828(11) 0.9076(9) 0.2586(3) 0.0382(14) Uani 1 1 d . . .
H9A H -0.8901 0.9980 0.2424 0.046 Uiso 1 1 calc R . .
H9B H -0.8745 0.8051 0.2512 0.046 Uiso 1 1 calc R . .
C10 C -0.7149(11) 0.9298(9) 0.3329(3) 0.0400(14) Uani 1 1 d . . .
H10A H -0.6272 1.0336 0.3412 0.048 Uiso 1 1 calc R . .
H10B H -0.6075 0.8402 0.3499 0.048 Uiso 1 1 calc R . .
C11 C -0.9399(12) 0.9307(10) 0.3691(3) 0.0441(15) Uani 1 1 d . . .
H11A H -1.0338 0.8309 0.3572 0.053 Uiso 1 1 calc R . .
H11B H -1.0406 1.0252 0.3537 0.053 Uiso 1 1 calc R . .
C12 C -0.8858(12) 0.9393(10) 0.4445(3) 0.0458(17) Uani 1 1 d . . .
H12A H -0.7850 0.8451 0.4601 0.055 Uiso 1 1 calc R . .
H12B H -0.7936 1.0396 0.4567 0.055 Uiso 1 1 calc R . .
C13 C -1.1134(12) 0.9389(10) 0.4788(3) 0.0491(18) Uani 1 1 d . . .
H13A H -1.2093 1.0367 0.4649 0.059 Uiso 1 1 calc R . .
H13B H -1.2103 0.8421 0.4642 0.059 Uiso 1 1 calc R . .
C14 C -1.0650(13) 0.9372(10) 0.5533(3) 0.0473(17) Uani 1 1 d . . .
H14A H -0.9701 1.0348 0.5680 0.057 Uiso 1 1 calc R . .
H14B H -0.9676 0.8402 0.5672 0.057 Uiso 1 1 calc R . .
C15 C -1.2950(13) 0.9347(10) 0.5873(3) 0.0456(16) Uani 1 1 d . . .
H15A H -1.3889 1.0342 0.5748 0.055 Uiso 1 1 calc R . .
H15B H -1.3933 0.8399 0.5711 0.055 Uiso 1 1 calc R . .
C16 C -1.2477(13) 0.9257(10) 0.6620(3) 0.0493(17) Uani 1 1 d . . .
H16A H -1.1528 0.8267 0.6746 0.059 Uiso 1 1 calc R . .
H16B H -1.1509 1.0211 0.6783 0.059 Uiso 1 1 calc R . .
C17 C -1.4774(14) 0.9217(11) 0.6952(3) 0.0575(19) Uani 1 1 d . . .
H17A H -1.4351 0.9162 0.7424 0.086 Uiso 1 1 calc R . .
H17B H -1.5724 0.8259 0.6802 0.086 Uiso 1 1 calc R . .
H17C H -1.5708 1.0205 0.6839 0.086 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
O1 0.045(3) 0.033(2) 0.0351(19) 0.0012(17) -0.0015(16) 0.004(2)
O2 0.047(3) 0.026(2) 0.045(2) 0.0043(17) 0.0008(19) 0.005(2)
O3 0.042(3) 0.028(2) 0.0346(18) -0.0038(16) -0.0040(16) 0.0073(19)
O4 0.042(3) 0.023(2) 0.047(2) 0.0017(16) 0.0018(18) 0.0034(19)
C1 0.036(4) 0.023(3) 0.043(3) -0.002(2) -0.001(2) -0.003(2)
C2 0.040(4) 0.026(3) 0.041(3) 0.002(2) 0.002(2) 0.001(3)
C3 0.043(4) 0.026(3) 0.037(3) 0.002(2) 0.006(2) 0.001(3)
C4 0.044(4) 0.022(3) 0.041(3) 0.002(2) 0.001(3) 0.002(3)
C5 0.043(4) 0.020(3) 0.035(3) -0.0029(19) 0.000(2) 0.005(3)
C6 0.043(4) 0.022(3) 0.042(3) 0.000(2) -0.004(3) 0.002(3)
C7 0.035(4) 0.025(3) 0.036(3) 0.003(2) 0.001(2) 0.005(2)
C8 0.035(4) 0.030(3) 0.039(3) -0.002(2) 0.001(2) -0.001(3)
C9 0.038(4) 0.041(3) 0.036(3) 0.001(2) 0.006(2) 0.003(3)
C10 0.039(4) 0.047(4) 0.034(3) -0.002(3) 0.006(2) 0.000(3)
C11 0.047(4) 0.051(4) 0.035(3) -0.002(3) 0.008(2) 0.007(3)
C12 0.046(4) 0.056(4) 0.035(3) -0.005(3) 0.005(3) -0.003(4)
C13 0.057(5) 0.058(5) 0.033(3) -0.003(3) 0.006(3) 0.004(4)
C14 0.054(4) 0.057(4) 0.032(3) -0.005(3) 0.008(3) -0.005(4)
C15 0.055(4) 0.047(4) 0.035(3) -0.002(3) 0.008(3) 0.000(3)
C16 0.060(5) 0.050(4) 0.039(3) -0.007(3) 0.011(3) -0.002(4)
C17 0.071(5) 0.062(5) 0.041(3) -0.004(3) 0.013(3) 0.002(4)
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C1 1.211(7) . ?
O2 C1 1.332(7) . ?
O3 C5 1.439(7) . ?
O4 C6 1.423(7) . ?
C1 C2 1.483(8) . ?
C2 C3 1.522(8) . ?
C3 C4 1.510(8) . ?
C4 C5 1.517(8) . ?
C5 C6 1.513(8) . ?
C5 C7 1.521(8) . ?
C7 C8 1.533(7) . ?
C8 C9 1.520(8) . ?
C9 C10 1.517(7) . ?
C10 C11 1.521(8) . ?
C11 C12 1.524(8) . ?
C12 C13 1.511(8) . ?
C13 C14 1.504(7) . ?
C14 C15 1.519(9) . ?
C15 C16 1.509(8) . ?
C16 C17 1.508(9) . ?
 
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
O1 C1 O2 122.9(5) . . ?
O1 C1 C2 125.9(5) . . ?
O2 C1 C2 111.1(5) . . ?
C1 C2 C3 116.0(5) . . ?
C4 C3 C2 113.2(5) . . ?
C3 C4 C5 115.2(5) . . ?
O3 C5 C6 108.4(5) . . ?
O3 C5 C4 106.0(4) . . ?
C6 C5 C4 109.3(5) . . ?
O3 C5 C7 107.1(5) . . ?
C6 C5 C7 112.4(5) . . ?
C4 C5 C7 113.3(5) . . ?
O4 C6 C5 110.3(5) . . ?
C5 C7 C8 118.1(5) . . ?
C9 C8 C7 110.1(5) . . ?
C10 C9 C8 115.8(5) . . ?
C9 C10 C11 111.4(5) . . ?
C10 C11 C12 114.6(5) . . ?
C13 C12 C11 113.1(5) . . ?
C14 C13 C12 114.2(6) . . ?
C13 C14 C15 113.8(5) . . ?
C16 C15 C14 114.0(5) . . ?
C17 C16 C15 113.5(6) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O1 C1 C2 C3 -3.8(9) . . . . ?
O2 C1 C2 C3 178.4(5) . . . . ?
C1 C2 C3 C4 -73.6(7) . . . . ?
C2 C3 C4 C5 -170.4(5) . . . . ?
C3 C4 C5 O3 -61.5(6) . . . . ?
C3 C4 C5 C6 -178.2(5) . . . . ?
C3 C4 C5 C7 55.6(6) . . . . ?
O3 C5 C6 O4 63.3(6) . . . . ?
C4 C5 C6 O4 178.4(4) . . . . ?
C7 C5 C6 O4 -54.9(6) . . . . ?
O3 C5 C7 C8 176.0(5) . . . . ?
C6 C5 C7 C8 -65.0(7) . . . . ?
C4 C5 C7 C8 59.4(6) . . . . ?
C5 C7 C8 C9 180.0(5) . . . . ?
C7 C8 C9 C10 172.6(6) . . . . ?
C8 C9 C10 C11 -179.1(6) . . . . ?
C9 C10 C11 C12 175.6(6) . . . . ?
C10 C11 C12 C13 -179.6(6) . . . . ?
C11 C12 C13 C14 176.6(7) . . . . ?
C12 C13 C14 C15 -179.3(7) . . . . ?
C13 C14 C15 C16 177.5(6) . . . . ?
C14 C15 C16 C17 -179.5(7) . . . . ?
 
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 HO2 O4  0.98(10) 1.63(11) 2.613(6) 179(9) 1_645
O3 HO3 O1  0.82 2.07 2.771(6) 142.8 2_455
O4 HO4 O3  0.82 2.42 2.840(6) 112.4 .
 
_diffrn_measured_fraction_theta_max    0.855
_diffrn_reflns_theta_full              71.19
_diffrn_measured_fraction_theta_full   0.855
_refine_diff_density_max    0.274
_refine_diff_density_min   -0.339
_refine_diff_density_rms    0.069