 
data_solution
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety           'C14 H24 O4'
_chemical_formula_sum
 'C14 H24 O4'
_chemical_formula_weight          256.33
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.910(6)
_cell_length_b                    27.07(3)
_cell_length_c                    5.947(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  101.01(16)
_cell_angle_gamma                 90.00
_cell_volume                      1408(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unk
_exptl_crystal_colour             unk
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.2
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.209
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              560
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             3701
_diffrn_reflns_av_R_equivalents   0.0632
_diffrn_reflns_av_sigmaI/netI     0.1869
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        31
_diffrn_reflns_limit_l_min        -6
_diffrn_reflns_limit_l_max        6
_diffrn_reflns_theta_min          3.01
_diffrn_reflns_theta_max          25.01
_reflns_number_total              2043
_reflns_number_gt                 1000
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0000P)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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2043
_refine_ls_number_parameters      164
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0885
_refine_ls_R_factor_gt            0.0500
_refine_ls_wR_factor_ref          0.1558
_refine_ls_wR_factor_gt           0.1123
_refine_ls_goodness_of_fit_ref    0.584
_refine_ls_restrained_S_all       0.584
_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
O2 O 0.0306(2) 0.07138(9) 0.9888(4) 0.0381(6) Uani 1 1 d . . .
O3 O -0.7082(3) 0.15335(9) 0.8913(4) 0.0439(7) Uani 1 1 d . . .
O1 O -0.1771(3) 0.04299(9) 0.4343(4) 0.0419(6) Uani 1 1 d . . .
O4 O -0.0665(3) 0.13906(9) 0.7938(4) 0.0436(6) Uani 1 1 d . . .
C2 C -0.1514(4) 0.04451(12) 0.6420(6) 0.0334(8) Uani 1 1 d . . .
C3 C -0.5503(4) 0.14265(13) 0.9769(5) 0.0343(8) Uani 1 1 d . . .
H3 H -0.4893 0.1530 0.8601 0.041 Uiso 1 1 calc R . .
C4 C -0.5614(4) 0.05864(13) 0.7794(6) 0.0358(8) Uani 1 1 d . . .
H4A H -0.6549 0.0708 0.6769 0.043 Uiso 1 1 calc R . .
H4B H -0.5776 0.0233 0.8112 0.043 Uiso 1 1 calc R . .
C5 C -0.5407(4) 0.08715(13) 1.0044(5) 0.0359(8) Uani 1 1 d . . .
H5A H -0.6200 0.0763 1.0896 0.043 Uiso 1 1 calc R . .
H5B H -0.4398 0.0786 1.0981 0.043 Uiso 1 1 calc R . .
C6 C -0.2794(3) 0.03993(13) 0.7772(5) 0.0344(8) Uani 1 1 d . . .
H6A H -0.2968 0.0046 0.8059 0.041 Uiso 1 1 calc R . .
H6B H -0.2478 0.0564 0.9275 0.041 Uiso 1 1 calc R . .
C17 C -0.4930(4) 0.17060(14) 1.1981(6) 0.0412(9) Uani 1 1 d . . .
H1A H -0.5425 0.1568 1.3197 0.049 Uiso 1 1 calc R . .
H1B H -0.5246 0.2056 1.1760 0.049 Uiso 1 1 calc R . .
C8 C 0.0121(4) 0.04741(14) 0.7695(6) 0.0391(9) Uani 1 1 d . . .
H8A H 0.0537 0.0135 0.7921 0.047 Uiso 1 1 calc R . .
H8B H 0.0733 0.0654 0.6735 0.047 Uiso 1 1 calc R . .
C9 C 0.0117(4) 0.14354(13) 1.2060(6) 0.0390(9) Uani 1 1 d . . .
H9A H 0.1227 0.1456 1.2685 0.047 Uiso 1 1 calc R . .
H9B H -0.0346 0.1222 1.3098 0.047 Uiso 1 1 calc R . .
C10 C -0.0116(4) 0.11979(13) 0.9748(6) 0.0349(8) Uani 1 1 d . . .
C11 C -0.4271(4) 0.06270(13) 0.6531(5) 0.0349(8) Uani 1 1 d . . .
H11A H -0.4565 0.0466 0.5017 0.042 Uiso 1 1 calc R . .
H11B H -0.4087 0.0981 0.6259 0.042 Uiso 1 1 calc R . .
C12 C -0.2305(4) 0.19835(14) 1.1292(6) 0.0440(9) Uani 1 1 d . . .
H12A H -0.2586 0.1864 0.9693 0.053 Uiso 1 1 calc R . .
H12B H -0.2617 0.2334 1.1309 0.053 Uiso 1 1 calc R . .
C13 C -0.7340(4) 0.19841(14) 0.7696(7) 0.0498(10) Uani 1 1 d . . .
H13A H -0.6941 0.2258 0.8712 0.075 Uiso 1 1 calc R . .
H13B H -0.8440 0.2029 0.7144 0.075 Uiso 1 1 calc R . .
H13C H -0.6817 0.1977 0.6389 0.075 Uiso 1 1 calc R . .
C14 C -0.3194(4) 0.16854(14) 1.2788(6) 0.0410(9) Uani 1 1 d . . .
H14A H -0.2860 0.1336 1.2809 0.049 Uiso 1 1 calc R . .
H14B H -0.2938 0.1812 1.4378 0.049 Uiso 1 1 calc R . .
C15 C -0.0568(4) 0.19515(14) 1.2051(6) 0.0454(10) Uani 1 1 d . . .
H15A H -0.0091 0.2163 1.1027 0.055 Uiso 1 1 calc R . .
H15B H -0.0289 0.2090 1.3617 0.055 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O2 C10 1.361(4) . ?
O2 C8 1.437(4) . ?
O3 C13 1.414(4) . ?
O3 C3 1.431(4) . ?
O1 C2 1.213(4) . ?
O4 C10 1.212(4) . ?
C2 C8 1.510(5) . ?
C2 C6 1.521(5) . ?
C3 C5 1.512(5) . ?
C3 C17 1.519(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.525(5) . ?
C4 C11 1.533(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.512(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 C14 1.530(5) . ?
C17 H1A 0.9900 . ?
C17 H1B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.496(5) . ?
C9 C15 1.524(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C15 1.529(5) . ?
C12 C14 1.530(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
 
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
C10 O2 C8 113.4(3) . . ?
C13 O3 C3 114.1(3) . . ?
O1 C2 C8 119.3(3) . . ?
O1 C2 C6 121.4(3) . . ?
C8 C2 C6 119.2(3) . . ?
O3 C3 C5 105.7(3) . . ?
O3 C3 C17 110.6(3) . . ?
C5 C3 C17 113.5(3) . . ?
O3 C3 H3 109.0 . . ?
C5 C3 H3 109.0 . . ?
C17 C3 H3 109.0 . . ?
C5 C4 C11 114.8(3) . . ?
C5 C4 H4A 108.6 . . ?
C11 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C11 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C3 C5 C4 114.4(3) . . ?
C3 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C3 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C11 C6 C2 112.3(3) . . ?
C11 C6 H6A 109.1 . . ?
C2 C6 H6A 109.1 . . ?
C11 C6 H6B 109.1 . . ?
C2 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C3 C17 C14 114.0(3) . . ?
C3 C17 H1A 108.8 . . ?
C14 C17 H1A 108.8 . . ?
C3 C17 H1B 108.8 . . ?
C14 C17 H1B 108.8 . . ?
H1A C17 H1B 107.7 . . ?
O2 C8 C2 114.3(3) . . ?
O2 C8 H8A 108.7 . . ?
C2 C8 H8A 108.7 . . ?
O2 C8 H8B 108.7 . . ?
C2 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C15 113.9(3) . . ?
C10 C9 H9A 108.8 . . ?
C15 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C15 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O4 C10 O2 121.9(3) . . ?
O4 C10 C9 126.4(3) . . ?
O2 C10 C9 111.7(3) . . ?
C6 C11 C4 114.8(3) . . ?
C6 C11 H11A 108.6 . . ?
C4 C11 H11A 108.6 . . ?
C6 C11 H11B 108.6 . . ?
C4 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C15 C12 C14 113.9(3) . . ?
C15 C12 H12A 108.8 . . ?
C14 C12 H12A 108.8 . . ?
C15 C12 H12B 108.8 . . ?
C14 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C14 C12 113.8(3) . . ?
C17 C14 H14A 108.8 . . ?
C12 C14 H14A 108.8 . . ?
C17 C14 H14B 108.8 . . ?
C12 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C9 C15 C12 115.8(3) . . ?
C9 C15 H15A 108.3 . . ?
C12 C15 H15A 108.3 . . ?
C9 C15 H15B 108.3 . . ?
C12 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
 
_diffrn_measured_fraction_theta_max    0.826
_diffrn_reflns_theta_full              25.01
_diffrn_measured_fraction_theta_full   0.826
_refine_diff_density_max    0.224
_refine_diff_density_min   -0.152
_refine_diff_density_rms    0.047
