 
data_an8809
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H24 O2'
_chemical_formula_weight          272.37
_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+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    7.2921(15)
_cell_length_b                    8.0475(16)
_cell_length_c                    26.378(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1547.9(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     273(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.50
_exptl_crystal_size_mid           0.48
_exptl_crystal_size_min           0.28
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.169
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              592
_exptl_absorpt_coefficient_mu     0.074
_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       273(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        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             2077
_diffrn_reflns_av_R_equivalents   0.0093
_diffrn_reflns_av_sigmaI/netI     0.0060
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        34
_diffrn_reflns_theta_min          2.65
_diffrn_reflns_theta_max          27.75
_reflns_number_total              2072
_reflns_number_gt                 1957
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_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 > 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)+(0.2000P)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          2072
_refine_ls_number_parameters      182
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1015
_refine_ls_R_factor_gt            0.0967
_refine_ls_wR_factor_ref          0.4262
_refine_ls_wR_factor_gt           0.4215
_refine_ls_goodness_of_fit_ref    2.266
_refine_ls_restrained_S_all       2.266
_refine_ls_shift/su_max           0.009
_refine_ls_shift/su_mean          0.001
 
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 0.3821(6) 0.0119(5) 0.86171(14) 0.0503(9) Uani 1 1 d . . .
H1 H 0.2715 0.0562 0.8455 0.060 Uiso 1 1 calc R . .
C2 C 0.3815(7) 0.2455(5) 0.92630(17) 0.0576(11) Uani 1 1 d . . .
H2A H 0.4587 0.3294 0.9418 0.069 Uiso 1 1 calc R . .
H2B H 0.2777 0.3018 0.9110 0.069 Uiso 1 1 calc R . .
C3 C 0.4914(5) 0.1567(5) 0.88436(14) 0.0468(9) Uani 1 1 d . . .
H3 H 0.5988 0.1076 0.9009 0.056 Uiso 1 1 calc R . .
O2 O 0.1399(11) -0.1566(7) 1.02390(16) 0.104(2) Uani 1 1 d . . .
C4 C 0.3252(6) -0.1020(5) 0.90463(15) 0.0494(9) Uani 1 1 d . . .
H4 H 0.4386 -0.1328 0.9222 0.059 Uiso 1 1 calc R . .
C5 C 0.4951(9) -0.0785(8) 0.8221(2) 0.0755(16) Uani 1 1 d . . .
H5A H 0.6012 -0.1289 0.8381 0.091 Uiso 1 1 calc R . .
H5B H 0.4222 -0.1665 0.8071 0.091 Uiso 1 1 calc R . .
C6 C 0.6627(8) 0.1852(8) 0.80349(17) 0.0663(13) Uani 1 1 d . . .
C7 C 0.2052(6) -0.0134(6) 0.94413(15) 0.0532(10) Uani 1 1 d . . .
C8 C 0.5654(7) 0.2793(6) 0.84454(17) 0.0573(11) Uani 1 1 d . . .
H8 H 0.4601 0.3356 0.8291 0.069 Uiso 1 1 calc R . .
C9 C 0.3112(8) 0.1282(6) 0.96761(17) 0.0644(12) Uani 1 1 d . . .
H9A H 0.4139 0.0845 0.9868 0.077 Uiso 1 1 calc R . .
H9B H 0.2325 0.1889 0.9908 0.077 Uiso 1 1 calc R . .
O1 O 1.0983(8) 0.3843(12) 0.8003(3) 0.128(3) Uani 1 1 d . . .
C10 C 0.0175(7) 0.0420(9) 0.9234(2) 0.0764(15) Uani 1 1 d . . .
H10A H -0.0546 0.0875 0.9505 0.115 Uiso 1 1 calc R . .
H10B H -0.0450 -0.0520 0.9091 0.115 Uiso 1 1 calc R . .
H10C H 0.0350 0.1249 0.8977 0.115 Uiso 1 1 calc R . .
C11 C 0.2245(10) -0.2648(7) 0.8939(2) 0.0757(15) Uani 1 1 d . . .
H11A H 0.3067 -0.3474 0.8797 0.091 Uiso 1 1 calc R . .
H11B H 0.1228 -0.2477 0.8708 0.091 Uiso 1 1 calc R . .
C12 C 0.8356(9) 0.2215(10) 0.7895(2) 0.0775(17) Uani 1 1 d . . .
H12 H 0.8942 0.1508 0.7668 0.093 Uiso 1 1 calc R . .
C13 C 0.1610(9) -0.1605(8) 0.9786(2) 0.0695(13) Uani 1 1 d . . .
C14 C 0.1563(11) -0.3171(7) 0.9468(2) 0.0771(16) Uani 1 1 d . . .
H14A H 0.0325 -0.3609 0.9449 0.093 Uiso 1 1 calc R . .
H14B H 0.2358 -0.4014 0.9612 0.093 Uiso 1 1 calc R . .
C15 C 0.5581(11) 0.0405(10) 0.78090(17) 0.087(2) Uani 1 1 d . . .
H15A H 0.4524 0.0819 0.7625 0.104 Uiso 1 1 calc R . .
H15B H 0.6362 -0.0181 0.7571 0.104 Uiso 1 1 calc R . .
C16 C 0.8192(11) 0.4906(11) 0.8335(3) 0.099(2) Uani 1 1 d . . .
H16A H 0.7519 0.5533 0.8081 0.119 Uiso 1 1 calc R . .
H16B H 0.8972 0.5676 0.8518 0.119 Uiso 1 1 calc R . .
C17 C 0.6863(9) 0.4125(8) 0.8696(2) 0.0768(15) Uani 1 1 d . . .
H17A H 0.7540 0.3623 0.8973 0.092 Uiso 1 1 calc R . .
H17B H 0.6082 0.4984 0.8838 0.092 Uiso 1 1 calc R . .
C18 C 0.9348(9) 0.3649(12) 0.8079(3) 0.088(2) Uani 1 1 d . . .
 
 
_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 C4 1.514(5) . ?
C1 C5 1.517(6) . ?
C1 C3 1.533(5) . ?
C1 H1 0.9800 . ?
C2 C9 1.530(6) . ?
C2 C3 1.542(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.538(5) . ?
C3 H3 0.9800 . ?
O2 C13 1.206(7) . ?
C4 C11 1.529(6) . ?
C4 C7 1.536(5) . ?
C4 H4 0.9800 . ?
C5 C15 1.520(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C12 1.346(8) . ?
C6 C8 1.500(7) . ?
C6 C15 1.514(8) . ?
C7 C9 1.509(6) . ?
C7 C13 1.527(7) . ?
C7 C10 1.540(6) . ?
C8 C17 1.538(7) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O1 C18 1.219(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C14 1.541(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C18 1.446(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.513(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C18 1.480(13) . ?
C16 C17 1.498(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
 
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
C4 C1 C5 111.9(4) . . ?
C4 C1 C3 108.1(3) . . ?
C5 C1 C3 110.5(3) . . ?
C4 C1 H1 108.7 . . ?
C5 C1 H1 108.7 . . ?
C3 C1 H1 108.7 . . ?
C9 C2 C3 113.5(3) . . ?
C9 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C9 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C8 C3 C1 113.8(3) . . ?
C8 C3 C2 112.0(3) . . ?
C1 C3 C2 111.2(3) . . ?
C8 C3 H3 106.4 . . ?
C1 C3 H3 106.4 . . ?
C2 C3 H3 106.4 . . ?
C1 C4 C11 120.8(4) . . ?
C1 C4 C7 112.5(3) . . ?
C11 C4 C7 104.5(4) . . ?
C1 C4 H4 106.0 . . ?
C11 C4 H4 106.0 . . ?
C7 C4 H4 106.0 . . ?
C15 C5 C1 110.8(5) . . ?
C15 C5 H5A 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C15 C5 H5B 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C12 C6 C8 122.1(6) . . ?
C12 C6 C15 122.0(6) . . ?
C8 C6 C15 115.7(5) . . ?
C9 C7 C13 116.7(4) . . ?
C9 C7 C10 112.5(5) . . ?
C13 C7 C10 104.3(4) . . ?
C9 C7 C4 109.7(4) . . ?
C13 C7 C4 99.4(4) . . ?
C10 C7 C4 113.6(4) . . ?
C6 C8 C3 109.6(4) . . ?
C6 C8 C17 113.0(5) . . ?
C3 C8 C17 110.7(4) . . ?
C6 C8 H8 107.8 . . ?
C3 C8 H8 107.8 . . ?
C17 C8 H8 107.8 . . ?
C7 C9 C2 110.2(3) . . ?
C7 C9 H9A 109.6 . . ?
C2 C9 H9A 109.6 . . ?
C7 C9 H9B 109.6 . . ?
C2 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 C14 102.8(4) . . ?
C4 C11 H11A 111.2 . . ?
C14 C11 H11A 111.2 . . ?
C4 C11 H11B 111.2 . . ?
C14 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C6 C12 C18 123.3(6) . . ?
C6 C12 H12 118.3 . . ?
C18 C12 H12 118.3 . . ?
O2 C13 C14 124.6(6) . . ?
O2 C13 C7 126.6(6) . . ?
C14 C13 C7 108.7(4) . . ?
C13 C14 C11 105.5(4) . . ?
C13 C14 H14A 110.6 . . ?
C11 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C11 C14 H14B 110.6 . . ?
H14A C14 H14B 108.8 . . ?
C5 C15 C6 110.8(4) . . ?
C5 C15 H15A 109.5 . . ?
C6 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C18 C16 C17 111.8(6) . . ?
C18 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C18 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C8 C17 C16 112.9(5) . . ?
C8 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C8 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
O1 C18 C12 122.4(10) . . ?
O1 C18 C16 123.0(9) . . ?
C12 C18 C16 114.5(5) . . ?
 
_diffrn_measured_fraction_theta_max    0.975
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.581
_refine_diff_density_min   -0.481
_refine_diff_density_rms    0.141
