data_2005src1571
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. N. Greeves
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H32 O2'
_chemical_formula_weight          304.46
 
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            monoclinic
_symmetry_space_group_name_H-M    C2/c
_symmetry_space_group_name_hall   '-C 2yc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    26.6843(11)
_cell_length_b                    16.3545(7)
_cell_length_c                    8.6878(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  98.881(2)
_cell_angle_gamma                 90.00
_cell_volume                      3746.0(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4374
_cell_measurement_theta_min       0.998
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Needle
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.36
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.080
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1344
_exptl_absorpt_coefficient_mu     0.067
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9762
_exptl_absorpt_correction_T_max   0.9980
_exptl_absorpt_process_details       'SADABS V2.10 (Sheldrick, G.M., 2003)'

_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    'graphite'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             23971
_diffrn_reflns_av_R_equivalents   0.1177
_diffrn_reflns_av_sigmaI/netI     0.1089
_diffrn_reflns_limit_h_min        -31
_diffrn_reflns_limit_h_max        31
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          3.44
_diffrn_reflns_theta_max          25.00
_reflns_number_total              3290
_reflns_number_gt                 2217
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_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)+(0.0190P)²+7.6688P] 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        0.0034(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3290
_refine_ls_number_parameters      207
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1435
_refine_ls_R_factor_gt            0.0914
_refine_ls_wR_factor_ref          0.1244
_refine_ls_wR_factor_gt           0.1113
_refine_ls_goodness_of_fit_ref    1.090
_refine_ls_restrained_S_all       1.090
_refine_ls_shift/su_max           0.007
_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 -0.05911(10) 0.08541(16) 0.0071(3) 0.0222(7) Uani 1 1 d . . .
H1A H -0.0962 0.0922 0.0009 0.027 Uiso 1 1 calc R . .
H1B H -0.0525 0.0584 -0.0899 0.027 Uiso 1 1 calc R . .
C2 C -0.03368(10) 0.16853(16) 0.0215(3) 0.0217(7) Uani 1 1 d . . .
H2A H -0.0398 0.1939 0.1204 0.026 Uiso 1 1 calc R . .
H2B H -0.0502 0.2035 -0.0646 0.026 Uiso 1 1 calc R . .
C3 C 0.02326(10) 0.16852(16) 0.0183(3) 0.0188(6) Uani 1 1 d . . .
H3 H 0.0405 0.1377 0.1111 0.023 Uiso 1 1 calc R . .
C4 C 0.04381(10) 0.25545(16) 0.0251(3) 0.0206(7) Uani 1 1 d . . .
H4A H 0.0347 0.2826 0.1189 0.025 Uiso 1 1 calc R . .
H4B H 0.0268 0.2857 -0.0670 0.025 Uiso 1 1 calc R . .
C5 C 0.10160(10) 0.26228(16) 0.0298(3) 0.0191(6) Uani 1 1 d . . .
H5 H 0.1099 0.2258 -0.0551 0.023 Uiso 1 1 calc R . .
C6 C 0.11654(10) 0.35052(16) -0.0151(3) 0.0214(7) Uani 1 1 d . . .
H6 H 0.1008 0.3898 0.0515 0.026 Uiso 1 1 calc R . .
C7 C 0.09437(10) 0.36738(18) -0.1820(3) 0.0261(7) Uani 1 1 d . . .
H7 H 0.1005 0.3280 -0.2573 0.031 Uiso 1 1 calc R . .
C8 C 0.06724(12) 0.4316(2) -0.2329(4) 0.0381(8) Uani 1 1 d . . .
H8A H 0.0601 0.4726 -0.1619 0.046 Uiso 1 1 calc R . .
H8B H 0.0547 0.4371 -0.3409 0.046 Uiso 1 1 calc R . .
C9 C 0.17442(11) 0.36568(17) 0.0139(3) 0.0274(7) Uani 1 1 d . . .
H9 H 0.1879 0.3427 0.1188 0.033 Uiso 1 1 calc R . .
C10 C 0.20194(12) 0.3226(2) -0.1048(4) 0.0401(9) Uani 1 1 d . . .
H10A H 0.1919 0.2649 -0.1122 0.060 Uiso 1 1 calc R . .
H10B H 0.2387 0.3265 -0.0715 0.060 Uiso 1 1 calc R . .
H10C H 0.1929 0.3487 -0.2069 0.060 Uiso 1 1 calc R . .
C11 C 0.18693(12) 0.45681(19) 0.0179(4) 0.0390(9) Uani 1 1 d . . .
H11A H 0.2235 0.4643 0.0491 0.058 Uiso 1 1 calc R . .
H11B H 0.1688 0.4842 0.0931 0.058 Uiso 1 1 calc R . .
H11C H 0.1765 0.4804 -0.0858 0.058 Uiso 1 1 calc R . .
C12 C 0.13174(10) 0.22871(16) 0.1813(3) 0.0189(6) Uani 1 1 d . . .
C13 C 0.15778(10) 0.15356(16) 0.1787(3) 0.0205(7) Uani 1 1 d . . .
C14 C 0.18692(10) 0.12394(18) 0.3151(3) 0.0253(7) Uani 1 1 d . . .
H14 H 0.2043 0.0735 0.3110 0.030 Uiso 1 1 calc R . .
C15 C 0.19138(10) 0.16522(18) 0.4558(3) 0.0248(7) Uani 1 1 d . . .
C16 C 0.16470(11) 0.23774(17) 0.4570(3) 0.0251(7) Uani 1 1 d . . .
H16 H 0.1667 0.2668 0.5524 0.030 Uiso 1 1 calc R . .
C17 C 0.13501(10) 0.27016(16) 0.3249(3) 0.0217(7) Uani 1 1 d . . .
C18 C 0.15645(11) 0.10189(17) 0.0332(3) 0.0279(7) Uani 1 1 d . . .
H18A H 0.1212 0.0891 -0.0096 0.042 Uiso 1 1 calc R . .
H18B H 0.1752 0.0510 0.0595 0.042 Uiso 1 1 calc R . .
H18C H 0.1721 0.1322 -0.0443 0.042 Uiso 1 1 calc R . .
C19 C 0.22309(12) 0.13273(19) 0.6016(3) 0.0361(8) Uani 1 1 d . . .
H19A H 0.2415 0.1779 0.6589 0.054 Uiso 1 1 calc R . .
H19B H 0.2474 0.0926 0.5734 0.054 Uiso 1 1 calc R . .
H19C H 0.2010 0.1065 0.6672 0.054 Uiso 1 1 calc R . .
C20 C 0.10951(11) 0.35130(17) 0.3458(3) 0.0299(8) Uani 1 1 d . . .
H20A H 0.1092 0.3611 0.4569 0.045 Uiso 1 1 calc R . .
H20B H 0.0746 0.3500 0.2905 0.045 Uiso 1 1 calc R . .
H20C H 0.1283 0.3953 0.3034 0.045 Uiso 1 1 calc R . .
O1 O -0.04020(8) 0.03521(12) 0.1383(2) 0.0348(5) Uani 1 1 d . . .
H1 H -0.0382 -0.0135 0.1090 0.052 Uiso 1 1 calc R . .
O2 O 0.03489(7) 0.12978(11) -0.12003(19) 0.0238(5) Uani 1 1 d . . .
H2 H 0.0124 0.1416 -0.1956 0.036 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
C1 O1 1.432(3) . ?
C1 C2 1.516(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.524(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.435(3) . ?
C3 C4 1.522(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.540(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.534(3) . ?
C5 C6 1.563(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.504(4) . ?
C6 C9 1.546(4) . ?
C6 H6 1.0000 . ?
C7 C8 1.313(4) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C11 1.526(4) . ?
C9 C10 1.528(4) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.411(4) . ?
C12 C13 1.414(4) . ?
C13 C14 1.399(4) . ?
C13 C18 1.517(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(4) . ?
C15 C19 1.507(4) . ?
C16 C17 1.394(4) . ?
C16 H16 0.9500 . ?
C17 C20 1.515(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1 H1 0.8400 . ?
O2 H2 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 C2 110.5(2) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 C3 115.7(2) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.4 . . ?
O2 C3 C4 108.8(2) . . ?
O2 C3 C2 111.1(2) . . ?
C4 C3 C2 110.7(2) . . ?
O2 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C3 C4 C5 115.0(2) . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
C12 C5 C4 112.7(2) . . ?
C12 C5 C6 115.1(2) . . ?
C4 C5 C6 110.7(2) . . ?
C12 C5 H5 105.8 . . ?
C4 C5 H5 105.8 . . ?
C6 C5 H5 105.8 . . ?
C7 C6 C9 111.2(2) . . ?
C7 C6 C5 109.4(2) . . ?
C9 C6 C5 113.2(2) . . ?
C7 C6 H6 107.6 . . ?
C9 C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
C8 C7 C6 125.9(3) . . ?
C8 C7 H7 117.1 . . ?
C6 C7 H7 117.1 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C11 C9 C10 109.9(2) . . ?
C11 C9 C6 111.7(2) . . ?
C10 C9 C6 112.8(2) . . ?
C11 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
C6 C9 H9 107.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 117.9(2) . . ?
C17 C12 C5 122.6(2) . . ?
C13 C12 C5 119.4(2) . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 C18 116.8(2) . . ?
C12 C13 C18 123.3(2) . . ?
C15 C14 C13 122.6(3) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C16 C15 C14 116.8(2) . . ?
C16 C15 C19 121.2(3) . . ?
C14 C15 C19 122.0(3) . . ?
C15 C16 C17 123.2(3) . . ?
C15 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C16 C17 C12 119.6(3) . . ?
C16 C17 C20 116.3(2) . . ?
C12 C17 C20 124.0(2) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O1 H1 O2  0.84 1.91 2.708(3) 159.3 5
O2 H2 O2  0.84 1.89 2.696(3) 160.3 2_554
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.251
_refine_diff_density_min   -0.364
_refine_diff_density_rms    0.045
