data_05src0006
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. A. K. Croft
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H22 O2'
_chemical_formula_sum
 'C21 H22 O2'
_chemical_formula_weight          306.39
 
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                    6.252(2)
_cell_length_b                    9.968(8)
_cell_length_c                    14.606(6)
_cell_angle_alpha                 70.840(7)
_cell_angle_beta                  85.920(6)
_cell_angle_gamma                 72.330(6)
_cell_volume                      818.8(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3723
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Rod
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.09
_exptl_crystal_size_mid           0.03
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.243
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              328
_exptl_absorpt_coefficient_mu     0.078
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9930
_exptl_absorpt_correction_T_max   0.9984
_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             16188
_diffrn_reflns_av_R_equivalents   0.0801
_diffrn_reflns_av_sigmaI/netI     0.0805
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.77
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3718
_reflns_number_gt                 2225
_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)+(0.0458P)²+0.4788P] 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        0.066(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3718
_refine_ls_number_parameters      277
_refine_ls_number_restraints      363
_refine_ls_R_factor_all           0.1431
_refine_ls_R_factor_gt            0.0792
_refine_ls_wR_factor_ref          0.1754
_refine_ls_wR_factor_gt           0.1531
_refine_ls_goodness_of_fit_ref    1.094
_refine_ls_restrained_S_all       1.071
_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 0.7702(4) 0.4737(3) 0.83578(18) 0.0416(6) Uani 1 1 d DU . .
H1 H 0.6025 0.5114 0.8307 0.050 Uiso 1 1 calc R A 1
C2 C 0.8592(4) 0.3447(3) 0.92641(17) 0.0386(6) Uani 1 1 d DU C .
C3 C 0.7347(4) 0.2842(3) 1.00123(18) 0.0434(6) Uani 1 1 d DU . .
H3 H 0.5762 0.3256 0.9998 0.052 Uiso 1 1 calc R C .
C4 C 0.8432(4) 0.1624(3) 1.07866(18) 0.0433(6) Uani 1 1 d DU C .
H4 H 0.7568 0.1200 1.1298 0.052 Uiso 1 1 calc R . .
C5 C 1.0734(4) 0.1010(3) 1.08323(17) 0.0406(6) Uani 1 1 d DU . .
C6 C 1.1973(4) 0.1635(2) 1.00744(18) 0.0403(6) Uani 1 1 d DU C .
H6 H 1.3560 0.1227 1.0092 0.048 Uiso 1 1 calc R . .
C7 C 1.0916(4) 0.2845(2) 0.92963(17) 0.0372(6) Uani 1 1 d DU . .
C8 C 1.2032(4) 0.3629(3) 0.84202(18) 0.0416(6) Uani 1 1 d DU C .
H8 H 1.3699 0.3170 0.8477 0.050 Uiso 1 1 calc R B 1
C9 C 1.1116(18) 0.358(3) 0.7530(11) 0.039(2) Uani 0.593(6) 1 d PDU C 1
C10 C 1.2353(11) 0.2996(12) 0.6860(6) 0.0381(16) Uani 0.593(6) 1 d PDU C 1
H10 H 1.3944 0.2612 0.6919 0.046 Uiso 0.593(6) 1 calc PR C 1
C11 C 1.1169(10) 0.2990(9) 0.6096(5) 0.0383(16) Uani 0.593(6) 1 d PDU C 1
H11 H 1.1972 0.2615 0.5611 0.046 Uiso 0.593(6) 1 calc PR C 1
C12 C 0.8856(10) 0.3516(9) 0.6019(5) 0.036(2) Uani 0.593(6) 1 d PDU C 1
C13 C 0.7684(11) 0.4127(9) 0.6708(5) 0.0354(15) Uani 0.593(6) 1 d PDU C 1
H13 H 0.6097 0.4534 0.6638 0.043 Uiso 0.593(6) 1 calc PR C 1
C14 C 0.8790(18) 0.416(2) 0.7501(10) 0.039(2) Uani 0.593(6) 1 d PDU C 1
C18 C 0.7609(8) 0.3443(5) 0.5195(3) 0.0509(14) Uani 0.593(6) 1 d PDU C 1
H18A H 0.7571 0.4304 0.4620 0.076 Uiso 0.593(6) 1 calc PR C 1
H18B H 0.6070 0.3451 0.5384 0.076 Uiso 0.593(6) 1 calc PR C 1
H18C H 0.8378 0.2526 0.5048 0.076 Uiso 0.593(6) 1 calc PR C 1
C31 C 0.832(3) 0.428(3) 0.7513(14) 0.048(4) Uani 0.407(6) 1 d PDU C 2
C32 C 0.6822(17) 0.4444(14) 0.6817(8) 0.042(3) Uani 0.407(6) 1 d PDU C 2
H32 H 0.5253 0.4887 0.6847 0.050 Uiso 0.407(6) 1 calc PR C 2
C33 C 0.7746(16) 0.3919(12) 0.6065(7) 0.044(2) Uani 0.407(6) 1 d PDU C 2
H33 H 0.6792 0.4009 0.5557 0.053 Uiso 0.407(6) 1 calc PR C 2
C34 C 1.0025(16) 0.3267(12) 0.6042(6) 0.040(3) Uani 0.407(6) 1 d PDU C 2
C35 C 1.1442(16) 0.3160(16) 0.6772(8) 0.043(3) Uani 0.407(6) 1 d PDU C 2
H35 H 1.3014 0.2745 0.6731 0.052 Uiso 0.407(6) 1 calc PR C 2
C36 C 1.063(2) 0.364(4) 0.7565(17) 0.044(4) Uani 0.407(6) 1 d PDU C 2
C37 C 1.0928(14) 0.2690(8) 0.5214(5) 0.062(2) Uani 0.407(6) 1 d PDU C 2
H37A H 1.0529 0.1781 0.5294 0.094 Uiso 0.407(6) 1 calc PR C 2
H37B H 1.2566 0.2469 0.5211 0.094 Uiso 0.407(6) 1 calc PR C 2
H37C H 1.0275 0.3444 0.4600 0.094 Uiso 0.407(6) 1 calc PR C 2
C15 C 0.8827(4) 0.5945(3) 0.83413(18) 0.0409(6) Uani 1 1 d U C .
H15 H 0.8388 0.6240 0.8936 0.049 Uiso 1 1 calc R . .
C16 C 1.1395(4) 0.5282(3) 0.83748(19) 0.0431(6) Uani 1 1 d U . .
H16A H 1.2040 0.5350 0.8952 0.052 Uiso 1 1 calc R C .
H16B H 1.2027 0.5855 0.7790 0.052 Uiso 1 1 calc R . .
C17 C 1.1885(5) -0.0328(3) 1.1672(2) 0.0537(7) Uani 1 1 d DU C .
H17A H 1.1118 -0.0258 1.2271 0.081 Uiso 1 1 calc R . .
H17B H 1.3453 -0.0361 1.1732 0.081 Uiso 1 1 calc R . .
H17C H 1.1834 -0.1234 1.1559 0.081 Uiso 1 1 calc R . .
C19 C 0.7972(5) 0.7298(3) 0.7469(2) 0.0447(6) Uani 1 1 d U . .
C20 C 0.4671(6) 0.9198(3) 0.6717(2) 0.0651(9) Uani 1 1 d U . .
H20A H 0.5744 0.9752 0.6402 0.078 Uiso 1 1 calc R C .
H20B H 0.3401 0.9880 0.6941 0.078 Uiso 1 1 calc R . .
C21 C 0.3830(6) 0.8683(4) 0.6010(3) 0.0810(11) Uani 1 1 d U C .
H21A H 0.5096 0.8035 0.5774 0.121 Uiso 1 1 calc R . .
H21B H 0.3061 0.9545 0.5463 0.121 Uiso 1 1 calc R . .
H21C H 0.2777 0.8130 0.6326 0.121 Uiso 1 1 calc R . .
O1 O 0.9029(3) 0.7762(2) 0.67925(15) 0.0622(6) Uani 1 1 d U C .
O2 O 0.5778(3) 0.7935(2) 0.75425(14) 0.0572(6) Uani 1 1 d U C .
 
 
_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 C31 1.440(10) . ?
C1 C2 1.506(4) . ?
C1 C15 1.561(3) . ?
C1 C14 1.574(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.376(4) . ?
C2 C7 1.391(3) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 C17 1.507(4) . ?
C6 C7 1.380(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.511(4) . ?
C8 C9 1.478(7) . ?
C8 C16 1.552(3) . ?
C8 C36 1.570(10) . ?
C8 H8 1.0000 . ?
C9 C10 1.374(7) . ?
C9 C14 1.390(7) . ?
C10 C11 1.385(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(7) . ?
C12 C18 1.512(6) . ?
C13 C14 1.404(7) . ?
C13 H13 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C31 C32 1.369(9) . ?
C31 C36 1.387(8) . ?
C32 C33 1.384(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.378(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.391(8) . ?
C34 C37 1.508(7) . ?
C35 C36 1.401(8) . ?
C35 H35 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C15 C19 1.503(4) . ?
C15 C16 1.537(4) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 O1 1.192(3) . ?
C19 O2 1.338(3) . ?
C20 O2 1.453(4) . ?
C20 C21 1.482(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
 
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
C31 C1 C2 110.3(12) . . ?
C31 C1 C15 109.4(12) . . ?
C2 C1 C15 106.3(2) . . ?
C2 C1 C14 104.8(7) . . ?
C15 C1 C14 104.5(7) . . ?
C31 C1 H1 104.0 . . ?
C2 C1 H1 113.4 . . ?
C15 C1 H1 113.4 . . ?
C14 C1 H1 113.4 . . ?
C3 C2 C7 120.0(2) . . ?
C3 C2 C1 126.6(2) . . ?
C7 C2 C1 113.4(2) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 C17 121.0(2) . . ?
C6 C5 C17 120.5(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 C8 126.5(2) . . ?
C2 C7 C8 113.5(2) . . ?
C9 C8 C7 109.8(10) . . ?
C9 C8 C16 107.9(10) . . ?
C7 C8 C16 106.7(2) . . ?
C7 C8 C36 101.7(14) . . ?
C16 C8 C36 104.8(14) . . ?
C9 C8 H8 110.8 . . ?
C7 C8 H8 110.8 . . ?
C16 C8 H8 110.8 . . ?
C36 C8 H8 120.9 . . ?
C10 C9 C14 125.3(7) . . ?
C10 C9 C8 125.5(8) . . ?
C14 C9 C8 109.2(7) . . ?
C9 C10 C11 116.8(6) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
C12 C11 C10 121.8(6) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.0(6) . . ?
C11 C12 C18 120.5(6) . . ?
C13 C12 C18 120.5(5) . . ?
C12 C13 C14 121.7(5) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C9 C14 C13 115.3(6) . . ?
C9 C14 C1 117.0(7) . . ?
C13 C14 C1 127.6(7) . . ?
C32 C31 C36 128.3(9) . . ?
C32 C31 C1 124.2(11) . . ?
C36 C31 C1 107.5(10) . . ?
C31 C32 C33 115.5(8) . . ?
C31 C32 H32 122.3 . . ?
C33 C32 H32 122.3 . . ?
C34 C33 C32 121.2(8) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C35 119.9(7) . . ?
C33 C34 C37 118.7(8) . . ?
C35 C34 C37 121.4(7) . . ?
C34 C35 C36 122.4(7) . . ?
C34 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C31 C36 C35 112.8(8) . . ?
C31 C36 C8 119.3(10) . . ?
C35 C36 C8 127.8(10) . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C19 C15 C16 112.9(2) . . ?
C19 C15 C1 109.8(2) . . ?
C16 C15 C1 109.5(2) . . ?
C19 C15 H15 108.2 . . ?
C16 C15 H15 108.2 . . ?
C1 C15 H15 108.2 . . ?
C15 C16 C8 110.0(2) . . ?
C15 C16 H16A 109.7 . . ?
C8 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C8 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C19 O2 123.1(3) . . ?
O1 C19 C15 126.7(3) . . ?
O2 C19 C15 110.1(2) . . ?
O2 C20 C21 110.2(3) . . ?
O2 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
O2 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 O2 C20 116.5(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.215
_refine_diff_density_min   -0.203
_refine_diff_density_rms    0.040
