 
data_05src0001
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H16 O3'
_chemical_formula_sum
 'C14 H16 O3'
_chemical_formula_weight          232.27
_chemical_absolute_configuration  unk
 
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   0.0000
 '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   0.0000
 '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)
_symmetry_space_group_name_hall   'P 2ac 2ab' 
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                    6.2521(3)
_cell_length_b                    9.3237(17)
_cell_length_c                    20.809(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1213.0(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1657
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        slab
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.34
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.272
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              496
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9705
_exptl_absorpt_correction_T_max   0.9895
_exptl_absorpt_process_details    'SADABS (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          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             27007
_diffrn_reflns_av_R_equivalents   0.0360
_diffrn_reflns_av_sigmaI/netI     0.0146
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          2.93
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1628
_reflns_number_gt                 1586
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'PLATON (Watkin, Pearce 1995)'
_computing_publication_material   SHELXL-97
 
_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)+(0.0352P)²+0.3636P] 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        0.044(7)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1628
_refine_ls_number_parameters      158
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0316
_refine_ls_R_factor_gt            0.0306
_refine_ls_wR_factor_ref          0.0802
_refine_ls_wR_factor_gt           0.0794
_refine_ls_goodness_of_fit_ref    1.142
_refine_ls_restrained_S_all       1.142
_refine_ls_shift/su_max           0.001
_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 0.9391(3) 0.74683(17) 0.89107(7) 0.0170(3) Uani 1 1 d . . .
C2 C 1.0261(3) 0.59890(17) 0.90884(7) 0.0182(3) Uani 1 1 d . . .
C3 C 1.1609(3) 0.55564(17) 0.85672(7) 0.0194(3) Uani 1 1 d . . .
H3 H 1.2366 0.4676 0.8534 0.023 Uiso 1 1 calc R . .
C4 C 1.1605(3) 0.66354(17) 0.81309(7) 0.0176(3) Uani 1 1 d . . .
C5 C 0.6987(3) 0.7394(2) 0.88127(8) 0.0227(4) Uani 1 1 d . . .
H5A H 0.6641 0.6577 0.8535 0.034 Uiso 1 1 calc R . .
H5B H 0.6490 0.8282 0.8610 0.034 Uiso 1 1 calc R . .
H5C H 0.6279 0.7275 0.9229 0.034 Uiso 1 1 calc R . .
C6 C 1.0125(3) 0.85932(17) 0.93941(7) 0.0170(3) Uani 1 1 d . . .
H6 H 0.9609 0.8300 0.9830 0.020 Uiso 1 1 calc R . .
C7 C 0.9317(3) 1.00992(17) 0.92589(8) 0.0219(4) Uani 1 1 d . . .
H7A H 0.7739 1.0080 0.9223 0.026 Uiso 1 1 calc R . .
H7B H 0.9900 1.0431 0.8842 0.026 Uiso 1 1 calc R . .
C8 C 0.9961(3) 1.11527(18) 0.97829(8) 0.0271(4) Uani 1 1 d . . .
H8A H 1.1519 1.1138 0.9835 0.041 Uiso 1 1 calc R . .
H8B H 0.9279 1.0878 1.0189 0.041 Uiso 1 1 calc R . .
H8C H 0.9501 1.2121 0.9662 0.041 Uiso 1 1 calc R . .
C9 C 1.2740(3) 0.67485(17) 0.75168(7) 0.0179(3) Uani 1 1 d . . .
C10 C 1.2259(3) 0.78523(18) 0.70865(7) 0.0210(4) Uani 1 1 d . . .
H10 H 1.1169 0.8527 0.7185 0.025 Uiso 1 1 calc R . .
C11 C 1.3385(3) 0.79576(18) 0.65135(8) 0.0247(4) Uani 1 1 d . . .
H11 H 1.3047 0.8697 0.6216 0.030 Uiso 1 1 calc R . .
C12 C 1.4998(3) 0.69900(18) 0.63727(8) 0.0251(4) Uani 1 1 d . . .
H12 H 1.5783 0.7082 0.5984 0.030 Uiso 1 1 calc R . .
C13 C 1.5474(3) 0.58858(19) 0.67975(8) 0.0244(4) Uani 1 1 d . . .
H13 H 1.6574 0.5218 0.6699 0.029 Uiso 1 1 calc R . .
C14 C 1.4335(3) 0.57645(18) 0.73647(8) 0.0217(4) Uani 1 1 d . . .
H14 H 1.4644 0.5002 0.7653 0.026 Uiso 1 1 calc R . .
O1 O 1.03780(19) 0.77696(12) 0.82886(5) 0.0176(3) Uani 1 1 d . . .
O2 O 0.9789(2) 0.53534(12) 0.95851(5) 0.0229(3) Uani 1 1 d . . .
O3 O 1.23970(19) 0.85185(14) 0.93907(6) 0.0216(3) Uani 1 1 d . . .
H3A H 1.2881 0.8923 0.9721 0.032 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 0.0159(7) 0.0200(7) 0.0149(7) 0.0001(6) 0.0011(6) 0.0007(6)
C2 0.0176(7) 0.0179(7) 0.0193(7) -0.0014(6) -0.0013(6) -0.0006(6)
C3 0.0197(8) 0.0181(7) 0.0202(7) -0.0019(6) 0.0017(6) 0.0021(6)
C4 0.0156(7) 0.0192(7) 0.0181(7) -0.0035(6) -0.0020(6) 0.0001(6)
C5 0.0174(8) 0.0258(8) 0.0250(8) -0.0016(7) -0.0026(7) -0.0002(7)
C6 0.0146(7) 0.0208(7) 0.0155(6) 0.0002(6) -0.0001(6) 0.0011(6)
C7 0.0232(8) 0.0212(8) 0.0211(7) -0.0020(6) -0.0020(6) 0.0039(7)
C8 0.0310(9) 0.0220(8) 0.0283(8) -0.0059(7) -0.0012(8) 0.0028(8)
C9 0.0184(7) 0.0197(7) 0.0155(7) -0.0032(6) -0.0009(6) -0.0020(7)
C10 0.0244(8) 0.0187(7) 0.0199(7) -0.0024(6) -0.0004(7) -0.0003(7)
C11 0.0345(10) 0.0219(8) 0.0176(7) 0.0004(6) -0.0004(7) -0.0035(8)
C12 0.0292(9) 0.0273(8) 0.0189(7) -0.0039(6) 0.0058(7) -0.0075(8)
C13 0.0240(8) 0.0263(8) 0.0230(8) -0.0053(7) 0.0029(7) -0.0002(8)
C14 0.0242(9) 0.0218(8) 0.0191(7) -0.0013(6) -0.0005(6) 0.0017(7)
O1 0.0200(6) 0.0184(5) 0.0143(5) -0.0005(4) 0.0010(4) 0.0034(5)
O2 0.0252(6) 0.0223(6) 0.0213(5) 0.0034(5) 0.0050(5) 0.0020(5)
O3 0.0156(6) 0.0266(6) 0.0227(6) -0.0051(5) -0.0023(5) 0.0028(5)
 
_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
C1 O1 1.4614(18) . ?
C1 C5 1.519(2) . ?
C1 C6 1.524(2) . ?
C1 C2 1.528(2) . ?
C2 O2 1.2275(19) . ?
C2 C3 1.432(2) . ?
C3 C4 1.355(2) . ?
C3 H3 0.9500 . ?
C4 O1 1.3469(19) . ?
C4 C9 1.466(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O3 1.422(2) . ?
C6 C7 1.518(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.522(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.391(2) . ?
C9 C10 1.397(2) . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O3 H3A 0.8400 . ?
 
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 C5 107.91(13) . . ?
O1 C1 C6 109.00(12) . . ?
C5 C1 C6 114.71(14) . . ?
O1 C1 C2 103.75(12) . . ?
C5 C1 C2 110.08(14) . . ?
C6 C1 C2 110.77(12) . . ?
O2 C2 C3 130.05(15) . . ?
O2 C2 C1 123.64(15) . . ?
C3 C2 C1 106.29(13) . . ?
C4 C3 C2 107.29(14) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
O1 C4 C3 114.88(14) . . ?
O1 C4 C9 115.58(14) . . ?
C3 C4 C9 129.54(15) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 C7 112.11(14) . . ?
O3 C6 C1 105.28(13) . . ?
C7 C6 C1 114.46(13) . . ?
O3 C6 H6 108.3 . . ?
C7 C6 H6 108.3 . . ?
C1 C6 H6 108.3 . . ?
C6 C7 C8 112.09(14) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 119.61(15) . . ?
C14 C9 C4 119.87(15) . . ?
C10 C9 C4 120.51(15) . . ?
C11 C10 C9 119.58(16) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.33(16) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.28(16) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.57(17) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C9 120.61(16) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C4 O1 C1 107.77(12) . . ?
C6 O3 H3A 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.226
_refine_diff_density_min   -0.159
_refine_diff_density_rms    0.033
