  
data_1034 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H20 O2' 
_chemical_formula_weight          232.31 
  
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 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
  
_cell_length_a                    8.9084(7) 
_cell_length_b                    10.0653(8) 
_cell_length_c                    14.7694(11) 
_cell_angle_alpha                 84.534(2) 
_cell_angle_beta                  84.355(2) 
_cell_angle_gamma                 78.480(2) 
_cell_volume                      1287.45(17) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     223(2) 
_cell_measurement_reflns_used     3560 
_cell_measurement_theta_min       2.34 
_cell_measurement_theta_max       28.5 
  
_exptl_crystal_description        blocks 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.6 
_exptl_crystal_size_mid           0.4 
_exptl_crystal_size_min           0.3 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_diffrn     1.199 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              504 
_exptl_absorpt_coefficient_mu     0.078 
_exptl_absorpt_correction_type    'sadabs (Sheldrick, 1996)' 
_exptl_absorpt_correction_T_min   0.2197 
_exptl_absorpt_correction_T_max   0.9748 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       223(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   ? 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             15389 
_diffrn_reflns_av_R_equivalents   0.0406 
_diffrn_reflns_av_sigmaI/netI     0.0519 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        20 
_diffrn_reflns_theta_min          1.39 
_diffrn_reflns_theta_max          30.05 
_reflns_number_total              7428 
_reflns_number_gt                 4396 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker AXS, SMART' 
_computing_cell_refinement        'Bruker AXS, SAINT' 
_computing_data_reduction         'Bruker AXS, SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker AXS, SHELXTL' 
_computing_publication_material   'Bruker AXS, 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)+(0.0485P)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     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          7428 
_refine_ls_number_parameters      313 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0865 
_refine_ls_R_factor_gt            0.0566 
_refine_ls_wR_factor_ref          0.1309 
_refine_ls_wR_factor_gt           0.1213 
_refine_ls_goodness_of_fit_ref    1.005 
_refine_ls_restrained_S_all       1.005 
_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 
O1 O 0.51898(10) 0.10892(8) 0.32760(6) 0.0432(2) Uani 1 1 d . . . 
C2 C 0.56501(14) 0.20015(11) 0.25550(8) 0.0376(3) Uani 1 1 d . . . 
H2 H 0.6784 0.1889 0.2509 0.045 Uiso 1 1 calc R . . 
C3 C 0.51497(14) 0.17276(12) 0.16483(8) 0.0385(3) Uani 1 1 d . . . 
H3 H 0.4024 0.1776 0.1732 0.046 Uiso 1 1 calc R . . 
C4 C 0.58739(17) 0.02729(13) 0.14426(9) 0.0518(3) Uani 1 1 d . . . 
H4A H 0.5504 0.0053 0.0882 0.062 Uiso 1 1 calc R . . 
H4B H 0.6995 0.0173 0.1354 0.062 Uiso 1 1 calc R . . 
C5 C 0.54370(17) -0.06845(13) 0.22402(9) 0.0531(4) Uani 1 1 d . . . 
H5A H 0.4327 -0.0656 0.2278 0.064 Uiso 1 1 calc R . . 
H5B H 0.5960 -0.1617 0.2135 0.064 Uiso 1 1 calc R . . 
C6 C 0.58708(16) -0.03020(12) 0.31325(9) 0.0478(3) Uani 1 1 d . . . 
H6 H 0.7003 -0.0413 0.3111 0.057 Uiso 1 1 calc R . . 
C7 C 0.54363(14) 0.28332(12) 0.09087(8) 0.0414(3) Uani 1 1 d . . . 
O8 O 0.45173(10) 0.41280(9) 0.11873(6) 0.0490(2) Uani 1 1 d . . . 
C9 C 0.44583(13) 0.43976(12) 0.20818(8) 0.0394(3) Uani 1 1 d . . . 
C10 C 0.38100(15) 0.57271(13) 0.22714(9) 0.0478(3) Uani 1 1 d . . . 
H10 H 0.3494 0.6380 0.1795 0.057 Uiso 1 1 calc R . . 
C11 C 0.36321(16) 0.60854(13) 0.31572(10) 0.0522(4) Uani 1 1 d . . . 
H11 H 0.3187 0.6983 0.3284 0.063 Uiso 1 1 calc R . . 
C12 C 0.41019(16) 0.51389(13) 0.38594(9) 0.0513(3) Uani 1 1 d . . . 
H12 H 0.3975 0.5384 0.4465 0.062 Uiso 1 1 calc R . . 
C13 C 0.47608(14) 0.38271(13) 0.36639(9) 0.0444(3) Uani 1 1 d . . . 
H13 H 0.5087 0.3183 0.4143 0.053 Uiso 1 1 calc R . . 
C14 C 0.49554(13) 0.34333(12) 0.27782(8) 0.0369(3) Uani 1 1 d . . . 
C15 C 0.53223(18) -0.11432(13) 0.39506(10) 0.0614(4) Uani 1 1 d . . . 
H15A H 0.5653 -0.0869 0.4499 0.092 Uiso 1 1 calc R . . 
H15B H 0.5752 -0.2097 0.3886 0.092 Uiso 1 1 calc R . . 
H15C H 0.4209 -0.1005 0.3993 0.092 Uiso 1 1 calc R . . 
C16 C 0.48060(17) 0.26505(15) 0.00242(9) 0.0569(4) Uani 1 1 d . . . 
H16A H 0.3788 0.2437 0.0152 0.085 Uiso 1 1 calc R . . 
H16B H 0.5480 0.1914 -0.0277 0.085 Uiso 1 1 calc R . . 
H16C H 0.4746 0.3484 -0.0370 0.085 Uiso 1 1 calc R . . 
C17 C 0.70898(15) 0.30187(14) 0.07403(9) 0.0541(4) Uani 1 1 d . . . 
H17A H 0.7169 0.3720 0.0249 0.081 Uiso 1 1 calc R . . 
H17B H 0.7739 0.2170 0.0573 0.081 Uiso 1 1 calc R . . 
H17C H 0.7420 0.3285 0.1291 0.081 Uiso 1 1 calc R . . 
O18 O 0.97561(10) 0.41753(9) 0.18174(6) 0.0504(2) Uani 1 1 d . . . 
C19 C 1.03798(14) 0.32118(12) 0.25154(8) 0.0405(3) Uani 1 1 d . . . 
H19 H 1.1386 0.3397 0.2642 0.049 Uiso 1 1 calc R . . 
C20 C 0.93174(14) 0.33047(12) 0.33853(8) 0.0420(3) Uani 1 1 d . . . 
H20 H 0.8296 0.3205 0.3221 0.050 Uiso 1 1 calc R . . 
C21 C 0.91288(17) 0.47299(13) 0.37028(10) 0.0560(4) Uani 1 1 d . . . 
H21A H 0.8387 0.4833 0.4239 0.067 Uiso 1 1 calc R . . 
H21B H 1.0115 0.4879 0.3873 0.067 Uiso 1 1 calc R . . 
C22 C 0.85644(18) 0.57612(13) 0.29329(11) 0.0618(4) Uani 1 1 d . . . 
H22A H 0.7513 0.5693 0.2831 0.074 Uiso 1 1 calc R . . 
H22B H 0.8541 0.6679 0.3111 0.074 Uiso 1 1 calc R . . 
C23 C 0.95687(17) 0.55491(13) 0.20568(10) 0.0578(4) Uani 1 1 d . . . 
H23 H 1.0591 0.5743 0.2138 0.069 Uiso 1 1 calc R . . 
C24 C 0.98464(15) 0.21237(13) 0.40801(9) 0.0472(3) Uani 1 1 d . . . 
O25 O 0.98303(11) 0.08543(9) 0.36748(6) 0.0534(3) Uani 1 1 d . . . 
C26 C 1.03524(14) 0.07302(13) 0.27816(9) 0.0444(3) Uani 1 1 d . . . 
C27 C 1.05657(16) -0.05670(14) 0.24753(11) 0.0584(4) Uani 1 1 d . . . 
H27 H 1.0393 -0.1306 0.2884 0.070 Uiso 1 1 calc R . . 
C28 C 1.10274(17) -0.07652(16) 0.15783(12) 0.0680(5) Uani 1 1 d . . . 
H28 H 1.1179 -0.1644 0.1376 0.082 Uiso 1 1 calc R . . 
C29 C 1.12708(17) 0.03059(18) 0.09707(11) 0.0671(4) Uani 1 1 d . . . 
H29 H 1.1576 0.0167 0.0354 0.080 Uiso 1 1 calc R . . 
C30 C 1.10623(15) 0.15866(15) 0.12750(9) 0.0536(4) Uani 1 1 d . . . 
H30 H 1.1229 0.2320 0.0859 0.064 Uiso 1 1 calc R . . 
C31 C 1.06127(13) 0.18203(13) 0.21811(8) 0.0406(3) Uani 1 1 d . . . 
C32 C 0.8926(2) 0.64261(16) 0.12432(12) 0.0817(5) Uani 1 1 d . . . 
H32A H 0.9629 0.6242 0.0706 0.123 Uiso 1 1 calc R . . 
H32B H 0.8798 0.7377 0.1356 0.123 Uiso 1 1 calc R . . 
H32C H 0.7938 0.6222 0.1145 0.123 Uiso 1 1 calc R . . 
C33 C 0.86920(18) 0.21057(16) 0.49001(10) 0.0731(5) Uani 1 1 d . . . 
H33A H 0.7674 0.2173 0.4697 0.110 Uiso 1 1 calc R . . 
H33B H 0.8699 0.2869 0.5253 0.110 Uiso 1 1 calc R . . 
H33C H 0.8961 0.1263 0.5276 0.110 Uiso 1 1 calc R . . 
C34 C 1.14477(17) 0.20442(15) 0.43691(10) 0.0636(4) Uani 1 1 d . . . 
H34A H 1.1670 0.1302 0.4836 0.095 Uiso 1 1 calc R . . 
H34B H 1.1509 0.2893 0.4611 0.095 Uiso 1 1 calc R . . 
H34C H 1.2190 0.1887 0.3846 0.095 Uiso 1 1 calc R . . 
  
  
_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 C2 1.4225(14) . ? 
O1 C6 1.4373(13) . ? 
C2 C14 1.5042(15) . ? 
C2 C3 1.5183(16) . ? 
C3 C4 1.5235(16) . ? 
C3 C7 1.5244(17) . ? 
C4 C5 1.5203(18) . ? 
C5 C6 1.5136(18) . ? 
C6 C15 1.5065(18) . ? 
C7 O8 1.4655(14) . ? 
C7 C16 1.5123(17) . ? 
C7 C17 1.5150(17) . ? 
O8 C9 1.3677(14) . ? 
C9 C14 1.3870(17) . ? 
C9 C10 1.3905(16) . ? 
C10 C11 1.3760(18) . ? 
C11 C12 1.3770(18) . ? 
C12 C13 1.3787(16) . ? 
C13 C14 1.3875(16) . ? 
O18 C19 1.4209(14) . ? 
O18 C23 1.4333(15) . ? 
C19 C31 1.4980(17) . ? 
C19 C20 1.5178(17) . ? 
C20 C21 1.5239(17) . ? 
C20 C24 1.5254(17) . ? 
C21 C22 1.5174(19) . ? 
C22 C23 1.506(2) . ? 
C23 C32 1.5108(19) . ? 
C24 O25 1.4649(15) . ? 
C24 C33 1.5109(18) . ? 
C24 C34 1.5137(19) . ? 
O25 C26 1.3637(15) . ? 
C26 C31 1.3857(17) . ? 
C26 C27 1.3936(17) . ? 
C27 C28 1.369(2) . ? 
C28 C29 1.373(2) . ? 
C29 C30 1.377(2) . ? 
C30 C31 1.3869(17) . ? 
  
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 
C2 O1 C6 111.92(9) . . ? 
O1 C2 C14 108.64(9) . . ? 
O1 C2 C3 111.44(9) . . ? 
C14 C2 C3 110.04(10) . . ? 
C2 C3 C4 108.68(10) . . ? 
C2 C3 C7 111.02(9) . . ? 
C4 C3 C7 116.08(10) . . ? 
C5 C4 C3 108.68(10) . . ? 
C6 C5 C4 111.50(11) . . ? 
O1 C6 C15 106.23(10) . . ? 
O1 C6 C5 110.41(10) . . ? 
C15 C6 C5 113.12(11) . . ? 
O8 C7 C16 103.58(10) . . ? 
O8 C7 C17 107.19(10) . . ? 
C16 C7 C17 110.59(11) . . ? 
O8 C7 C3 107.79(9) . . ? 
C16 C7 C3 111.72(10) . . ? 
C17 C7 C3 115.16(11) . . ? 
C9 O8 C7 118.24(9) . . ? 
O8 C9 C14 124.08(11) . . ? 
O8 C9 C10 115.45(11) . . ? 
C14 C9 C10 120.44(12) . . ? 
C11 C10 C9 119.92(12) . . ? 
C10 C11 C12 120.51(12) . . ? 
C11 C12 C13 119.19(13) . . ? 
C12 C13 C14 121.71(12) . . ? 
C9 C14 C13 118.22(11) . . ? 
C9 C14 C2 119.39(11) . . ? 
C13 C14 C2 122.37(11) . . ? 
C19 O18 C23 112.46(10) . . ? 
O18 C19 C31 108.38(10) . . ? 
O18 C19 C20 110.82(10) . . ? 
C31 C19 C20 110.51(10) . . ? 
C19 C20 C21 108.56(11) . . ? 
C19 C20 C24 110.81(10) . . ? 
C21 C20 C24 116.48(11) . . ? 
C22 C21 C20 108.88(11) . . ? 
C23 C22 C21 112.26(12) . . ? 
O18 C23 C22 110.98(11) . . ? 
O18 C23 C32 105.40(12) . . ? 
C22 C23 C32 113.81(13) . . ? 
O25 C24 C33 103.38(12) . . ? 
O25 C24 C34 107.57(10) . . ? 
C33 C24 C34 111.02(12) . . ? 
O25 C24 C20 108.11(10) . . ? 
C33 C24 C20 111.25(11) . . ? 
C34 C24 C20 114.75(12) . . ? 
C26 O25 C24 118.93(10) . . ? 
O25 C26 C31 123.35(11) . . ? 
O25 C26 C27 116.44(12) . . ? 
C31 C26 C27 120.16(13) . . ? 
C28 C27 C26 119.98(14) . . ? 
C27 C28 C29 120.68(14) . . ? 
C28 C29 C30 119.25(14) . . ? 
C29 C30 C31 121.56(14) . . ? 
C26 C31 C30 118.36(12) . . ? 
C26 C31 C19 119.84(11) . . ? 
C30 C31 C19 121.79(12) . . ? 
  
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              30.05 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.196 
_refine_diff_density_min   -0.276 
_refine_diff_density_rms    0.050 
  
