data_2005src1567
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. N. Greeves
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H34 O'
_chemical_formula_sum
 'C21 H34 O'
_chemical_formula_weight          302.48
 
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            tetragonal
_symmetry_space_group_name_H-M    I-4
_symmetry_space_group_name_hall   I-4
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z'
 'y, -x, -z'
 '-y, x, -z'
 'x+1/2, y+1/2, z+1/2'
 '-x+1/2, -y+1/2, z+1/2'
 'y+1/2, -x+1/2, -z+1/2'
 '-y+1/2, x+1/2, -z+1/2'
 
_cell_length_a                    16.8137(4)
_cell_length_b                    16.8137(4)
_cell_length_c                    13.9960(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3956.68(19)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2350
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Shard
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.09
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.016
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1344
_exptl_absorpt_coefficient_mu     0.060
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9812
_exptl_absorpt_correction_T_max   0.9946
_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    '10cm confocal mirrors'
_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             16279
_diffrn_reflns_av_R_equivalents   0.0538
_diffrn_reflns_av_sigmaI/netI     0.0373
_diffrn_reflns_limit_h_min        -21
_diffrn_reflns_limit_h_max        21
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.08
_diffrn_reflns_theta_max          27.46
_reflns_number_total              2349
_reflns_number_gt                 2036
_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)+(0.0460P)²+1.5648P] 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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    ?
_refine_ls_number_reflns          2349
_refine_ls_number_parameters      235
_refine_ls_number_restraints      4
_refine_ls_R_factor_all           0.0570
_refine_ls_R_factor_gt            0.0460
_refine_ls_wR_factor_ref          0.1088
_refine_ls_wR_factor_gt           0.1039
_refine_ls_goodness_of_fit_ref    1.070
_refine_ls_restrained_S_all       1.073
_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 0.3750(2) -0.0105(2) -0.0378(3) 0.0655(10) Uani 1 1 d . . .
H1A H 0.4054 0.0151 -0.0861 0.079 Uiso 1 1 calc R . .
H1B H 0.3737 -0.0669 -0.0345 0.079 Uiso 1 1 calc R . .
C2 C 0.33486(15) 0.03209(15) 0.0242(2) 0.0423(6) Uani 1 1 d . . .
H2 H 0.3054 0.0037 0.0711 0.051 Uiso 1 1 calc R . .
C3 C 0.33078(13) 0.12114(13) 0.02856(17) 0.0303(5) Uani 1 1 d . . .
H3 H 0.3531 0.1418 -0.0328 0.036 Uiso 1 1 calc R . .
C4 C 0.24190(13) 0.14778(13) 0.03329(17) 0.0277(5) Uani 1 1 d . . .
H4 H 0.2157 0.1107 0.0795 0.033 Uiso 1 1 calc R . .
C5 C 0.20116(14) 0.13260(16) -0.06401(18) 0.0359(6) Uani 1 1 d . B .
H5A H 0.2247 0.1690 -0.1119 0.043 Uiso 1 1 calc R . .
H5B H 0.2132 0.0775 -0.0844 0.043 Uiso 1 1 calc R . .
C6 C 0.11140(14) 0.14376(17) -0.06432(19) 0.0385(6) Uani 1 1 d D . .
H6 H 0.1019 0.1951 -0.0300 0.046 Uiso 1 1 calc R A 1
C7 C 0.0767(2) 0.1558(3) -0.1645(3) 0.0340(11) Uani 0.637(8) 1 d PD B 1
H7A H 0.0189 0.1661 -0.1590 0.041 Uiso 0.637(8) 1 calc PR B 1
H7B H 0.1015 0.2034 -0.1937 0.041 Uiso 0.637(8) 1 calc PR B 1
C8 C 0.0898(2) 0.0850(3) -0.2296(3) 0.0414(13) Uani 0.637(8) 1 d PD B 1
H8A H 0.0693 0.0364 -0.1980 0.050 Uiso 0.637(8) 1 calc PR B 1
H8B H 0.1475 0.0778 -0.2404 0.050 Uiso 0.637(8) 1 calc PR B 1
C9 C 0.0482(5) 0.0956(5) -0.3252(5) 0.0520(18) Uani 0.637(8) 1 d PD B 1
H9A H -0.0093 0.0998 -0.3149 0.078 Uiso 0.637(8) 1 calc PR B 1
H9B H 0.0595 0.0497 -0.3662 0.078 Uiso 0.637(8) 1 calc PR B 1
H9C H 0.0676 0.1442 -0.3561 0.078 Uiso 0.637(8) 1 calc PR B 1
C27 C 0.0718(4) 0.1057(5) -0.1596(5) 0.034(2) Uani 0.363(8) 1 d PD B 2
H27A H 0.0963 0.0534 -0.1737 0.040 Uiso 0.363(8) 1 calc PR B 2
H27B H 0.0140 0.0979 -0.1500 0.040 Uiso 0.363(8) 1 calc PR B 2
C28 C 0.0862(5) 0.1628(4) -0.2417(5) 0.041(2) Uani 0.363(8) 1 d PD B 2
H28A H 0.1441 0.1677 -0.2534 0.049 Uiso 0.363(8) 1 calc PR B 2
H28B H 0.0654 0.2160 -0.2249 0.049 Uiso 0.363(8) 1 calc PR B 2
C29 C 0.0449(9) 0.1326(7) -0.3328(8) 0.047(3) Uani 0.363(8) 1 d PD B 2
H29A H 0.0673 0.0810 -0.3510 0.071 Uiso 0.363(8) 1 calc PR B 2
H29B H 0.0531 0.1709 -0.3847 0.071 Uiso 0.363(8) 1 calc PR B 2
H29C H -0.0123 0.1267 -0.3207 0.071 Uiso 0.363(8) 1 calc PR B 2
C10 C 0.38338(14) 0.15388(13) 0.11014(18) 0.0315(5) Uani 1 1 d . . .
H10 H 0.3733 0.2124 0.1145 0.038 Uiso 1 1 calc R . .
C11 C 0.47175(15) 0.14254(18) 0.0863(2) 0.0447(7) Uani 1 1 d . . .
H11A H 0.5043 0.1689 0.1350 0.067 Uiso 1 1 calc R . .
H11B H 0.4831 0.1659 0.0236 0.067 Uiso 1 1 calc R . .
H11C H 0.4843 0.0856 0.0851 0.067 Uiso 1 1 calc R . .
C12 C 0.36475(16) 0.11824(18) 0.2070(2) 0.0440(6) Uani 1 1 d . . .
H12A H 0.3762 0.0611 0.2059 0.066 Uiso 1 1 calc R . .
H12B H 0.3084 0.1266 0.2219 0.066 Uiso 1 1 calc R . .
H12C H 0.3976 0.1440 0.2559 0.066 Uiso 1 1 calc R . .
C13 C 0.22776(13) 0.23153(13) 0.07283(16) 0.0278(5) Uani 1 1 d . . .
C14 C 0.26179(14) 0.30031(14) 0.03233(18) 0.0335(5) Uani 1 1 d . . .
C15 C 0.24813(14) 0.37403(14) 0.07399(18) 0.0337(5) Uani 1 1 d . . .
H15 H 0.2715 0.4198 0.0458 0.040 Uiso 1 1 calc R . .
C16 C 0.20196(13) 0.38362(14) 0.15473(19) 0.0330(5) Uani 1 1 d . . .
C17 C 0.16805(13) 0.31603(13) 0.19371(18) 0.0294(5) Uani 1 1 d . . .
H17 H 0.1361 0.3210 0.2494 0.035 Uiso 1 1 calc R . .
C18 C 0.17917(12) 0.24086(13) 0.15405(17) 0.0277(5) Uani 1 1 d . . .
C19 C 0.31476(18) 0.29959(17) -0.0552(2) 0.0486(7) Uani 1 1 d . . .
H19A H 0.3258 0.3544 -0.0751 0.073 Uiso 1 1 calc R . .
H19B H 0.2879 0.2713 -0.1072 0.073 Uiso 1 1 calc R . .
H19C H 0.3649 0.2727 -0.0400 0.073 Uiso 1 1 calc R . .
C20 C 0.18654(17) 0.46473(15) 0.1972(2) 0.0458(7) Uani 1 1 d . . .
H20A H 0.2175 0.5047 0.1625 0.069 Uiso 1 1 calc R . .
H20B H 0.2023 0.4648 0.2646 0.069 Uiso 1 1 calc R . .
H20C H 0.1298 0.4773 0.1921 0.069 Uiso 1 1 calc R . .
C21 C 0.13638(14) 0.17162(14) 0.20024(19) 0.0352(5) Uani 1 1 d . . .
H21A H 0.1023 0.1913 0.2519 0.053 Uiso 1 1 calc R . .
H21B H 0.1755 0.1343 0.2264 0.053 Uiso 1 1 calc R . .
H21C H 0.1037 0.1444 0.1524 0.053 Uiso 1 1 calc R . .
O1 O 0.07863(10) 0.08367(10) -0.00390(15) 0.0407(5) Uani 1 1 d . B .
H1 H 0.0293 0.0904 0.0009 0.061 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 C2 1.313(4) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.500(3) . ?
C2 H2 0.9500 . ?
C3 C10 1.546(3) . ?
C3 C4 1.562(3) . ?
C3 H3 1.0000 . ?
C4 C13 1.531(3) . ?
C4 C5 1.546(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O1 1.428(3) . ?
C6 C7 1.532(5) . ?
C6 C27 1.621(8) . ?
C6 H6 1.0000 . ?
C7 C8 1.516(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.520(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C27 C28 1.517(10) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.538(11) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C10 C12 1.515(4) . ?
C10 C11 1.535(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.409(3) . ?
C13 C14 1.409(3) . ?
C14 C15 1.389(3) . ?
C14 C19 1.515(4) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 C20 1.510(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 C21 1.514(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O1 H1 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
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 126.5(3) . . ?
C1 C2 H2 116.8 . . ?
C3 C2 H2 116.8 . . ?
C2 C3 C10 111.05(19) . . ?
C2 C3 C4 109.38(19) . . ?
C10 C3 C4 114.46(19) . . ?
C2 C3 H3 107.2 . . ?
C10 C3 H3 107.2 . . ?
C4 C3 H3 107.2 . . ?
C13 C4 C5 113.66(18) . . ?
C13 C4 C3 115.32(18) . . ?
C5 C4 C3 109.84(18) . . ?
C13 C4 H4 105.7 . . ?
C5 C4 H4 105.7 . . ?
C3 C4 H4 105.7 . . ?
C6 C5 C4 115.0(2) . . ?
C6 C5 H5A 108.5 . . ?
C4 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
O1 C6 C5 107.1(2) . . ?
O1 C6 C7 119.3(3) . . ?
C5 C6 C7 113.4(2) . . ?
O1 C6 C27 92.8(3) . . ?
C5 C6 C27 111.2(3) . . ?
O1 C6 H6 105.3 . . ?
C5 C6 H6 105.3 . . ?
C7 C6 H6 105.3 . . ?
C27 C6 H6 132.0 . . ?
C8 C7 C6 113.0(3) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 111.7(4) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C28 C27 C6 107.9(6) . . ?
C28 C27 H27A 110.1 . . ?
C6 C27 H27A 110.1 . . ?
C28 C27 H27B 110.1 . . ?
C6 C27 H27B 110.1 . . ?
H27A C27 H27B 108.4 . . ?
C27 C28 C29 110.3(7) . . ?
C27 C28 H28A 109.6 . . ?
C29 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
C29 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C12 C10 C11 110.2(2) . . ?
C12 C10 C3 113.7(2) . . ?
C11 C10 C3 110.4(2) . . ?
C12 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C3 C10 H10 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 117.9(2) . . ?
C18 C13 C4 118.95(19) . . ?
C14 C13 C4 123.1(2) . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 C19 116.3(2) . . ?
C13 C14 C19 123.9(2) . . ?
C16 C15 C14 122.7(2) . . ?
C16 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C15 C16 C17 117.3(2) . . ?
C15 C16 C20 121.6(2) . . ?
C17 C16 C20 121.0(2) . . ?
C16 C17 C18 122.2(2) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C13 120.0(2) . . ?
C17 C18 C21 117.6(2) . . ?
C13 C18 C21 122.3(2) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C6 O1 H1 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 O1  0.84 1.91 2.732(2) 165.9 4
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.46
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.132
_refine_diff_density_min   -0.147
_refine_diff_density_rms    0.030
