 
data_25_0m 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C14 H18 O3'
_chemical_formula_sum 
 'C14 H18 O3' 
_chemical_formula_weight          234.28 
 
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            triclinic
_symmetry_space_group_name_H-M    'P -1'
_symmetry_space_group_name_hall   '-P 1'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    6.57590(10) 
_cell_length_b                    7.08190(10) 
_cell_length_c                    13.0369(3) 
_cell_angle_alpha                 90.6670(10) 
_cell_angle_beta                  99.8020(10) 
_cell_angle_gamma                 100.1960(10) 
_cell_volume                      588.269(18) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     6624
_cell_measurement_theta_min       2.9252
_cell_measurement_theta_max       28.2750
 
_exptl_crystal_description        lamellar
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.1 
_exptl_crystal_density_meas       'not measured'  
_exptl_crystal_density_diffrn     1.323 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              252 
_exptl_absorpt_coefficient_mu     0.092 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details    'SADABS V2008/1 (Bruker AXS Inc.)' 
_exptl_absorpt_correction_T_min   0.7182 
_exptl_absorpt_correction_T_max   0.7457 

 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             10548 
_diffrn_reflns_av_R_equivalents   0.0149 
_diffrn_reflns_av_sigmaI/netI     0.0163 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        8 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          1.59 
_diffrn_reflns_theta_max          28.28 
_reflns_number_total              2909 
_reflns_number_gt                 2589 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection         'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction         'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material   'SHELXTL'
 
_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)+(0.0582P)²+0.1481P] where P=(Fo²+2Fc²)/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_number_reflns          2909 
_refine_ls_number_parameters      154 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0412 
_refine_ls_R_factor_gt            0.0370 
_refine_ls_wR_factor_ref          0.1017 
_refine_ls_wR_factor_gt           0.0980 
_refine_ls_goodness_of_fit_ref    1.064 
_refine_ls_restrained_S_all       1.064 
_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 -0.13584(17) 1.18864(15) 0.27389(8) 0.0199(2) Uani 1 1 d . . . 
C2 C -0.02051(16) 1.06589(15) 0.31774(8) 0.0179(2) Uani 1 1 d . . . 
C3 C 0.17128(15) 1.02376(14) 0.28022(8) 0.0149(2) Uani 1 1 d . . . 
C4 C 0.16236(14) 0.80993(13) 0.25267(7) 0.01161(19) Uani 1 1 d . . . 
C5 C -0.02766(14) 0.73713(14) 0.16581(7) 0.0139(2) Uani 1 1 d . . . 
C6 C 0.05227(15) 0.76548(14) 0.06342(7) 0.0140(2) Uani 1 1 d . . . 
C7 C 0.29014(14) 0.82367(14) 0.08495(7) 0.0140(2) Uani 1 1 d . . . 
C8 C 0.35154(14) 0.78128(13) 0.20016(7) 0.01202(19) Uani 1 1 d . . . 
C9 C 0.37564(15) 0.57348(14) 0.22264(7) 0.0142(2) Uani 1 1 d . . . 
C10 C 0.33655(14) 0.55537(14) 0.33479(7) 0.01295(19) Uani 1 1 d . . . 
C11 C 0.16756(14) 0.67594(13) 0.34724(7) 0.01269(19) Uani 1 1 d . . . 
C12 C 0.24621(16) 0.76674(15) 0.45696(8) 0.0175(2) Uani 1 1 d . . . 
C13 C 0.52707(15) 0.65303(14) 0.41182(7) 0.0152(2) Uani 1 1 d . . . 
C14 C 0.39585(16) 0.73155(16) 0.00720(8) 0.0198(2) Uani 1 1 d . . . 
O1 O 0.47289(11) 0.77478(11) 0.47799(5) 0.01876(17) Uani 1 1 d . . . 
O2 O 0.70675(11) 0.63199(12) 0.41758(6) 0.02256(19) Uani 1 1 d . . . 
O3 O -0.05636(11) 0.74323(12) -0.02256(6) 0.02151(18) Uani 1 1 d . . . 
H18 H 0.2658 0.4812 0.1723 0.025 Uiso 1 1 d . . . 
H17 H 0.0304 0.5967 0.3481 0.017 Uiso 1 1 d . . . 
H16 H -0.1500 0.8056 0.1625 0.033 Uiso 1 1 d . . . 
H15 H 0.1875 0.6848 0.5063 0.023 Uiso 1 1 d . . . 
H14 H 0.3026 0.4245 0.3580 0.027 Uiso 1 1 d . . . 
H13 H 0.4864 0.8726 0.2325 0.020 Uiso 1 1 d . . . 
H12 H 0.3188 0.9634 0.0789 0.026 Uiso 1 1 d . . . 
H11 H 0.1910 1.0989 0.2120 0.019 Uiso 1 1 d . . . 
H10 H -0.0841 0.5945 0.1653 0.018 Uiso 1 1 d . . . 
H9 H 0.5536 0.7635 0.0237 0.025 Uiso 1 1 d . . . 
H8 H 0.2269 0.9017 0.4695 0.014 Uiso 1 1 d . . . 
H7 H 0.2965 1.0674 0.3342 0.024 Uiso 1 1 d . . . 
H6 H 0.5167 0.5441 0.2110 0.017 Uiso 1 1 d . . . 
H5 H -0.2597 1.2187 0.3052 0.023 Uiso 1 1 d . . . 
H4 H 0.3514 0.7758 -0.0632 0.027 Uiso 1 1 d . . . 
H3 H -0.1007 1.2550 0.2104 0.027 Uiso 1 1 d . . . 
H2 H 0.3524 0.5860 0.0043 0.029 Uiso 1 1 d . . . 
H1 H -0.0570 0.9940 0.3795 0.029 Uiso 1 1 d . . . 
 
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 0.0214(5) 0.0174(5) 0.0199(5) -0.0023(4) -0.0007(4) 0.0051(4) 
C2 0.0225(5) 0.0160(5) 0.0163(5) -0.0003(4) 0.0040(4) 0.0058(4) 
C3 0.0170(4) 0.0118(4) 0.0157(5) -0.0002(3) 0.0015(4) 0.0033(3) 
C4 0.0115(4) 0.0121(4) 0.0105(4) 0.0000(3) 0.0005(3) 0.0017(3) 
C5 0.0118(4) 0.0159(5) 0.0129(4) 0.0004(3) 0.0007(3) 0.0014(3) 
C6 0.0145(4) 0.0131(4) 0.0139(4) 0.0003(3) 0.0009(3) 0.0029(3) 
C7 0.0134(4) 0.0158(5) 0.0120(4) 0.0017(3) 0.0014(3) 0.0014(3) 
C8 0.0110(4) 0.0131(4) 0.0114(4) 0.0007(3) 0.0013(3) 0.0011(3) 
C9 0.0157(4) 0.0143(5) 0.0134(4) 0.0006(3) 0.0030(3) 0.0042(3) 
C10 0.0138(4) 0.0119(4) 0.0131(4) 0.0020(3) 0.0015(3) 0.0027(3) 
C11 0.0133(4) 0.0132(4) 0.0118(4) 0.0015(3) 0.0023(3) 0.0028(3) 
C12 0.0201(5) 0.0210(5) 0.0126(4) 0.0017(4) 0.0015(4) 0.0085(4) 
C13 0.0169(4) 0.0145(5) 0.0135(4) 0.0048(4) 0.0010(3) 0.0025(4) 
C14 0.0167(5) 0.0292(6) 0.0142(5) 0.0017(4) 0.0042(4) 0.0049(4) 
O1 0.0197(4) 0.0191(4) 0.0155(4) -0.0017(3) -0.0028(3) 0.0040(3) 
O2 0.0149(3) 0.0300(4) 0.0225(4) 0.0068(3) 0.0009(3) 0.0054(3) 
O3 0.0178(4) 0.0312(4) 0.0137(4) 0.0007(3) -0.0016(3) 0.0036(3) 
 
_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 C2 1.3248(14) . ? 
C2 C3 1.5029(14) . ? 
C3 C4 1.5409(13) . ? 
C4 C5 1.5447(13) . ? 
C4 C8 1.5600(13) . ? 
C4 C11 1.5639(13) . ? 
C5 C6 1.5185(13) . ? 
C6 O3 1.2145(12) . ? 
C6 C7 1.5215(13) . ? 
C7 C14 1.5236(14) . ? 
C7 C8 1.5350(13) . ? 
C8 C9 1.5341(13) . ? 
C9 C10 1.5300(13) . ? 
C10 C13 1.5183(13) . ? 
C10 C11 1.5442(13) . ? 
C11 C12 1.5284(13) . ? 
C12 O1 1.4597(12) . ? 
C13 O2 1.2068(12) . ? 
C13 O1 1.3456(12) . ? 
 
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 
C1 C2 C3 123.80(9) . . ? 
C2 C3 C4 114.24(8) . . ? 
C3 C4 C5 109.91(8) . . ? 
C3 C4 C8 111.16(7) . . ? 
C5 C4 C8 102.43(7) . . ? 
C3 C4 C11 115.14(8) . . ? 
C5 C4 C11 111.69(7) . . ? 
C8 C4 C11 105.71(7) . . ? 
C6 C5 C4 106.23(7) . . ? 
O3 C6 C5 125.36(9) . . ? 
O3 C6 C7 125.10(9) . . ? 
C5 C6 C7 109.53(8) . . ? 
C6 C7 C14 113.05(8) . . ? 
C6 C7 C8 103.81(7) . . ? 
C14 C7 C8 117.03(8) . . ? 
C9 C8 C7 115.82(8) . . ? 
C9 C8 C4 103.79(7) . . ? 
C7 C8 C4 105.86(7) . . ? 
C10 C9 C8 102.60(7) . . ? 
C13 C10 C9 111.18(8) . . ? 
C13 C10 C11 103.51(8) . . ? 
C9 C10 C11 107.15(7) . . ? 
C12 C11 C10 102.12(7) . . ? 
C12 C11 C4 118.59(8) . . ? 
C10 C11 C4 104.83(7) . . ? 
O1 C12 C11 106.53(8) . . ? 
O2 C13 O1 121.26(9) . . ? 
O2 C13 C10 127.85(9) . . ? 
O1 C13 C10 110.90(8) . . ? 
C13 O1 C12 110.09(7) . . ? 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              28.28 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.386 
_refine_diff_density_min   -0.199 
_refine_diff_density_rms    0.045 
