data_04sjc0831
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H20 O5'
_chemical_formula_weight          268.30
 
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    Pbca
 
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'
 '-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                    16.4963(18)
_cell_length_b                    8.325(3)
_cell_length_c                    20.061(6)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2755.0(14)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3533
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.17
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.294
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1152
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9760
_exptl_absorpt_correction_T_max   0.9981
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   '10cm confocal mirrors'
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             20102
_diffrn_reflns_av_R_equivalents   0.0905
_diffrn_reflns_av_sigmaI/netI     0.0670
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -26
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          2.92
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3155
_reflns_number_gt                 1990
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0458P)²+0.9768P] 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        0.0049(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3155
_refine_ls_number_parameters      173
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0977
_refine_ls_R_factor_gt            0.0487
_refine_ls_wR_factor_ref          0.1192
_refine_ls_wR_factor_gt           0.1008
_refine_ls_goodness_of_fit_ref    0.974
_refine_ls_restrained_S_all       0.974
_refine_ls_shift/su_max           0.024
_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
C1 C 0.10650(11) 0.6028(2) 0.15602(9) 0.0265(4) Uani 1 1 d . . .
C2 C 0.07667(12) 0.6156(2) 0.09181(10) 0.0346(5) Uani 1 1 d . . .
H2 H 0.0274 0.6713 0.0837 0.042 Uiso 1 1 calc R . .
C3 C 0.11916(13) 0.5466(3) 0.03925(10) 0.0414(5) Uani 1 1 d . . .
H3 H 0.0986 0.5546 -0.0049 0.050 Uiso 1 1 calc R . .
C4 C 0.19043(12) 0.4672(3) 0.05067(10) 0.0390(5) Uani 1 1 d . . .
H4 H 0.2188 0.4203 0.0144 0.047 Uiso 1 1 calc R . .
C5 C 0.22184(11) 0.4543(2) 0.11478(10) 0.0326(5) Uani 1 1 d . . .
H5 H 0.2715 0.3992 0.1223 0.039 Uiso 1 1 calc R . .
C6 C 0.18018(10) 0.5223(2) 0.16750(9) 0.0253(4) Uani 1 1 d . . .
C7 C -0.01388(11) 0.7071(2) 0.20599(9) 0.0300(4) Uani 1 1 d . . .
H7A H -0.0461 0.6209 0.1847 0.036 Uiso 1 1 calc R . .
H7B H -0.0184 0.8053 0.1784 0.036 Uiso 1 1 calc R . .
C8 C -0.04430(11) 0.7387(2) 0.27450(9) 0.0320(5) Uani 1 1 d . . .
H8A H -0.0061 0.8102 0.2984 0.038 Uiso 1 1 calc R . .
H8B H -0.0977 0.7928 0.2723 0.038 Uiso 1 1 calc R . .
C9 C -0.06303(11) 0.6089(3) 0.37886(9) 0.0335(5) Uani 1 1 d . . .
H9A H -0.0920 0.5139 0.3965 0.040 Uiso 1 1 calc R . .
H9B H -0.0973 0.7045 0.3870 0.040 Uiso 1 1 calc R . .
C10 C 0.01605(11) 0.6282(2) 0.41580(9) 0.0317(5) Uani 1 1 d . . .
H10A H 0.0478 0.7175 0.3963 0.038 Uiso 1 1 calc R . .
H10B H 0.0055 0.6532 0.4633 0.038 Uiso 1 1 calc R . .
C11 C 0.14053(11) 0.4944(2) 0.43276(10) 0.0330(5) Uani 1 1 d . . .
H11A H 0.1414 0.5122 0.4815 0.040 Uiso 1 1 calc R . .
H11B H 0.1675 0.5867 0.4109 0.040 Uiso 1 1 calc R . .
C12 C 0.18465(12) 0.3416(2) 0.41604(10) 0.0345(5) Uani 1 1 d . . .
H12A H 0.2370 0.3404 0.4402 0.041 Uiso 1 1 calc R . .
H12B H 0.1522 0.2494 0.4321 0.041 Uiso 1 1 calc R . .
C13 C 0.27036(11) 0.4037(2) 0.32405(10) 0.0335(5) Uani 1 1 d . . .
H13A H 0.3198 0.3469 0.3392 0.040 Uiso 1 1 calc R . .
H13B H 0.2715 0.5141 0.3423 0.040 Uiso 1 1 calc R . .
C14 C 0.26840(10) 0.4094(2) 0.24999(10) 0.0311(5) Uani 1 1 d . . .
H14A H 0.3207 0.4495 0.2323 0.037 Uiso 1 1 calc R . .
H14B H 0.2582 0.3011 0.2315 0.037 Uiso 1 1 calc R . .
O1 O 0.06936(7) 0.65908(15) 0.21157(6) 0.0291(3) Uani 1 1 d . . .
O2 O -0.05174(7) 0.59002(15) 0.30918(6) 0.0299(3) Uani 1 1 d . . .
O3 O 0.05977(7) 0.48216(16) 0.41035(6) 0.0315(3) Uani 1 1 d . . .
O4 O 0.19986(7) 0.32128(15) 0.34725(6) 0.0316(3) Uani 1 1 d . . .
O5 O 0.20375(7) 0.51684(14) 0.23245(6) 0.0270(3) Uani 1 1 d . . .
 
 
_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 O1 1.355(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 O5 1.361(2) . ?
C7 O1 1.435(2) . ?
C7 C8 1.487(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.425(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O2 1.419(2) . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O3 1.418(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.410(2) . ?
C11 C12 1.503(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O4 1.413(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O4 1.428(2) . ?
C13 C14 1.487(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O5 1.436(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 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
O1 C1 C2 125.33(17) . . ?
O1 C1 C6 114.87(16) . . ?
C2 C1 C6 119.78(17) . . ?
C1 C2 C3 119.67(19) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.83(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.37(19) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
O5 C6 C5 125.22(17) . . ?
O5 C6 C1 114.81(15) . . ?
C5 C6 C1 119.95(17) . . ?
O1 C7 C8 107.48(14) . . ?
O1 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O1 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
O2 C8 C7 109.07(15) . . ?
O2 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
O2 C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O2 C9 C10 112.47(15) . . ?
O2 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
O2 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
O3 C10 C9 108.09(15) . . ?
O3 C10 H10A 110.1 . . ?
C9 C10 H10A 110.1 . . ?
O3 C10 H10B 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
O3 C11 C12 108.99(15) . . ?
O3 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O3 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O4 C12 C11 113.91(16) . . ?
O4 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
O4 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O4 C13 C14 108.87(15) . . ?
O4 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
O4 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O5 C14 C13 106.33(15) . . ?
O5 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
O5 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C1 O1 C7 117.71(14) . . ?
C9 O2 C8 113.31(14) . . ?
C11 O3 C10 113.21(14) . . ?
C12 O4 C13 113.92(14) . . ?
C6 O5 C14 117.90(14) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.212
_refine_diff_density_min   -0.186
_refine_diff_density_rms    0.048
