 
data_2008src1140
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C15 H22 O3'
_chemical_formula_weight          250.33
 
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    P212121
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    5.25570(10)
_cell_length_b                    10.3241(4)
_cell_length_c                    24.6007(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1334.84(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     9636
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        blade
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.62
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.246
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              544
_exptl_absorpt_coefficient_mu     0.085
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9492
_exptl_absorpt_correction_T_max   0.9949
_exptl_absorpt_process_details    'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
 ?
;
 
_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 Roper 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             10722
_diffrn_reflns_av_R_equivalents   0.0467
_diffrn_reflns_av_sigmaI/netI     0.0371
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -30
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          3.31
_diffrn_reflns_theta_max          27.47
_reflns_number_total              1796
_reflns_number_gt                 1592
_reflns_threshold_expression      >2σ(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     ?
_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)+(0.0398P)²+0.2489P] 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    10(10)
_refine_ls_number_reflns          1796
_refine_ls_number_parameters      163
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0479
_refine_ls_R_factor_gt            0.0392
_refine_ls_wR_factor_ref          0.0887
_refine_ls_wR_factor_gt           0.0847
_refine_ls_goodness_of_fit_ref    1.054
_refine_ls_restrained_S_all       1.054
_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 0.4790(4) 0.53406(18) 0.15979(7) 0.0199(4) Uani 1 1 d . . .
H1 H 0.6316 0.5844 0.1718 0.024 Uiso 1 1 calc R . .
C2 C 0.3799(4) 0.45906(19) 0.20800(7) 0.0255(4) Uani 1 1 d . . .
H2A H 0.5198 0.4077 0.2242 0.031 Uiso 1 1 calc R . .
H2B H 0.3169 0.5201 0.2359 0.031 Uiso 1 1 calc R . .
C4 C 0.2077(4) 0.24552(19) 0.20098(7) 0.0230(4) Uani 1 1 d . . .
C5 C -0.0112(4) 0.1660(2) 0.18047(9) 0.0284(5) Uani 1 1 d . . .
H5A H -0.1633 0.1858 0.2027 0.034 Uiso 1 1 calc R . .
H5B H 0.0295 0.0732 0.1857 0.034 Uiso 1 1 calc R . .
C6 C -0.0764(4) 0.18842(19) 0.12046(8) 0.0281(5) Uani 1 1 d . . .
H6A H -0.2173 0.1300 0.1099 0.034 Uiso 1 1 calc R . .
H6B H -0.1355 0.2787 0.1156 0.034 Uiso 1 1 calc R . .
C7 C 0.1467(4) 0.16460(19) 0.08403(8) 0.0273(5) Uani 1 1 d . . .
H7 H 0.2040 0.0776 0.0811 0.033 Uiso 1 1 calc R . .
C8 C 0.2725(4) 0.2526(2) 0.05541(7) 0.0271(5) Uani 1 1 d . . .
H8 H 0.4119 0.2223 0.0344 0.032 Uiso 1 1 calc R . .
C9 C 0.2179(4) 0.39508(19) 0.05278(8) 0.0256(5) Uani 1 1 d . . .
H9A H 0.0779 0.4156 0.0783 0.031 Uiso 1 1 calc R . .
H9B H 0.1594 0.4171 0.0157 0.031 Uiso 1 1 calc R . .
C10 C 0.4479(4) 0.47861(19) 0.06680(7) 0.0226(4) Uani 1 1 d . . .
H10 H 0.5792 0.4684 0.0377 0.027 Uiso 1 1 calc R . .
C11 C 0.3821(3) 0.62198(18) 0.07266(7) 0.0200(4) Uani 1 1 d . . .
H11 H 0.2398 0.6461 0.0476 0.024 Uiso 1 1 calc R . .
C12 C 0.6156(4) 0.70731(19) 0.06225(8) 0.0258(4) Uani 1 1 d . . .
H12A H 0.7649 0.6686 0.0806 0.031 Uiso 1 1 calc R . .
H12B H 0.6512 0.7091 0.0227 0.031 Uiso 1 1 calc R . .
C13 C 0.5801(4) 0.84542(19) 0.08249(8) 0.0283(5) Uani 1 1 d . . .
H13A H 0.4393 0.8871 0.0623 0.034 Uiso 1 1 calc R . .
H13B H 0.7372 0.8958 0.0757 0.034 Uiso 1 1 calc R . .
C14 C 0.5199(4) 0.8463(2) 0.14327(8) 0.0262(5) Uani 1 1 d . . .
H14A H 0.6673 0.8114 0.1636 0.031 Uiso 1 1 calc R . .
H14B H 0.4914 0.9366 0.1554 0.031 Uiso 1 1 calc R . .
C15 C 0.2848(4) 0.76543(18) 0.15603(7) 0.0229(4) Uani 1 1 d . . .
H15A H 0.1329 0.8104 0.1415 0.028 Uiso 1 1 calc R . .
H15B H 0.2652 0.7595 0.1960 0.028 Uiso 1 1 calc R . .
C16 C 0.2941(3) 0.62788(19) 0.13237(7) 0.0194(4) Uani 1 1 d . . .
H16 H 0.1193 0.5900 0.1346 0.023 Uiso 1 1 calc R . .
O3 O 0.1749(3) 0.37301(13) 0.19152(5) 0.0262(3) Uani 1 1 d . . .
O4 O 0.3893(3) 0.20128(14) 0.22439(6) 0.0355(4) Uani 1 1 d . . .
O17 O 0.5586(2) 0.44394(13) 0.11846(5) 0.0241(3) 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 O17 1.440(2) . ?
C1 C2 1.509(3) . ?
C1 C16 1.529(2) . ?
C1 H1 1.0000 . ?
C2 O3 1.454(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 O4 1.205(2) . ?
C4 O3 1.348(2) . ?
C4 C5 1.501(3) . ?
C5 C6 1.533(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.496(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.326(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.500(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.524(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O17 1.443(2) . ?
C10 C11 1.527(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.532(3) . ?
C11 C16 1.541(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.528(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.524(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.535(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 1.0000 . ?
 
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
O17 C1 C2 108.88(15) . . ?
O17 C1 C16 106.41(13) . . ?
C2 C1 C16 116.90(16) . . ?
O17 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
C16 C1 H1 108.1 . . ?
O3 C2 C1 110.50(15) . . ?
O3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
O3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O4 C4 O3 123.63(19) . . ?
O4 C4 C5 124.10(19) . . ?
O3 C4 C5 112.24(17) . . ?
C4 C5 C6 114.36(17) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C5 112.14(16) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 126.60(19) . . ?
C8 C7 H7 116.7 . . ?
C6 C7 H7 116.7 . . ?
C7 C8 C9 126.82(19) . . ?
C7 C8 H8 116.6 . . ?
C9 C8 H8 116.6 . . ?
C8 C9 C10 113.15(17) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
O17 C10 C9 112.25(16) . . ?
O17 C10 C11 104.41(14) . . ?
C9 C10 C11 112.96(16) . . ?
O17 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C10 C11 C12 111.11(15) . . ?
C10 C11 C16 101.32(14) . . ?
C12 C11 C16 112.13(15) . . ?
C10 C11 H11 110.7 . . ?
C12 C11 H11 110.7 . . ?
C16 C11 H11 110.7 . . ?
C13 C12 C11 112.70(16) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 110.54(16) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C13 111.48(17) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 113.73(16) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C1 C16 C15 116.04(15) . . ?
C1 C16 C11 101.82(14) . . ?
C15 C16 C11 114.04(16) . . ?
C1 C16 H16 108.2 . . ?
C15 C16 H16 108.2 . . ?
C11 C16 H16 108.2 . . ?
C4 O3 C2 117.00(16) . . ?
C1 O17 C10 110.14(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.201
_refine_diff_density_min   -0.208
_refine_diff_density_rms    0.065
