 
data_2009src0664
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety
 'C17 H14 O'
_chemical_formula_sum
 'C17 H14 O'
_chemical_formula_weight          234.28
 
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    'C 2/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                    13.3991(5)
_cell_length_b                    8.2341(3)
_cell_length_c                    22.8014(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.356(2)
_cell_angle_gamma                 90.00
_cell_volume                      2500.20(16)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     24100
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.245
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              992
_exptl_absorpt_coefficient_mu     0.076
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9776
_exptl_absorpt_correction_T_max   0.9925
_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             17562
_diffrn_reflns_av_R_equivalents   0.0602
_diffrn_reflns_av_sigmaI/netI     0.0440
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          27.47
_reflns_number_total              2874
_reflns_number_gt                 2077
_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     'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.0925P)²+1.0572P] 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          2874
_refine_ls_number_parameters      165
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0821
_refine_ls_R_factor_gt            0.0553
_refine_ls_wR_factor_ref          0.1638
_refine_ls_wR_factor_gt           0.1463
_refine_ls_goodness_of_fit_ref    1.046
_refine_ls_restrained_S_all       1.046
_refine_ls_shift/su_max           0.002
_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 0.63120(12) 0.3436(2) 0.66115(7) 0.0252(4) Uani 1 1 d . . .
C2 C 0.59131(13) 0.4631(2) 0.69332(7) 0.0301(4) Uani 1 1 d . . .
H2 H 0.5211 0.4641 0.6961 0.036 Uiso 1 1 calc R . .
C3 C 0.65196(14) 0.5838(2) 0.72209(7) 0.0333(4) Uani 1 1 d . . .
H3 H 0.6228 0.6652 0.7443 0.040 Uiso 1 1 calc R . .
C4 C 0.75283(14) 0.5845(2) 0.71825(7) 0.0320(4) Uani 1 1 d . . .
H4 H 0.7938 0.6657 0.7383 0.038 Uiso 1 1 calc R . .
C5 C 0.90222(13) 0.4677(2) 0.68100(7) 0.0303(4) Uani 1 1 d . . .
H5 H 0.9419 0.5521 0.7000 0.036 Uiso 1 1 calc R . .
C6 C 0.94690(13) 0.3510(2) 0.65066(7) 0.0312(4) Uani 1 1 d . . .
H6 H 1.0174 0.3536 0.6488 0.037 Uiso 1 1 calc R . .
C7 C 0.88810(13) 0.2258(2) 0.62192(7) 0.0284(4) Uani 1 1 d . . .
H7 H 0.9202 0.1440 0.6014 0.034 Uiso 1 1 calc R . .
C8 C 0.78569(12) 0.21914(19) 0.62281(7) 0.0231(4) Uani 1 1 d . . .
C9 C 0.73710(12) 0.33973(19) 0.65469(6) 0.0218(4) Uani 1 1 d . . .
C10 C 0.79686(13) 0.4651(2) 0.68464(6) 0.0255(4) Uani 1 1 d . . .
C11 C 0.73182(12) 0.08046(19) 0.59069(7) 0.0235(4) Uani 1 1 d . . .
C12 C 0.73932(13) -0.0760(2) 0.61442(7) 0.0282(4) Uani 1 1 d . . .
H12 H 0.7763 -0.0930 0.6519 0.034 Uiso 1 1 calc R . .
C13 C 0.69361(13) -0.2067(2) 0.58410(7) 0.0288(4) Uani 1 1 d . . .
H13 H 0.6995 -0.3118 0.6013 0.035 Uiso 1 1 calc R . .
C14 C 0.63907(13) -0.1873(2) 0.52877(7) 0.0266(4) Uani 1 1 d . . .
C15 C 0.63186(13) -0.0315(2) 0.50476(7) 0.0290(4) Uani 1 1 d . . .
H15 H 0.5954 -0.0151 0.4671 0.035 Uiso 1 1 calc R . .
C16 C 0.67718(13) 0.0998(2) 0.53505(7) 0.0278(4) Uani 1 1 d . . .
H16 H 0.6711 0.2048 0.5178 0.033 Uiso 1 1 calc R . .
C17 C 0.58913(14) -0.3307(2) 0.49711(8) 0.0359(5) Uani 1 1 d . . .
H17A H 0.6355 -0.4231 0.4999 0.054 Uiso 1 1 calc R . .
H17B H 0.5708 -0.3031 0.4555 0.054 Uiso 1 1 calc R . .
H17C H 0.5285 -0.3595 0.5152 0.054 Uiso 1 1 calc R . .
O1 O 0.56484(9) 0.22958(15) 0.63758(6) 0.0347(4) Uani 1 1 d . . .
H1 H 0.5954 0.1596 0.6196 0.052 Uiso 1 1 calc R . .
 
 
_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 O1 1.362(2) . ?
C1 C2 1.371(2) . ?
C1 C9 1.443(2) . ?
C2 C3 1.400(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(3) . ?
C3 H3 0.9500 . ?
C4 C10 1.415(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.361(3) . ?
C5 C10 1.423(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.429(2) . ?
C8 C11 1.498(2) . ?
C9 C10 1.432(2) . ?
C11 C12 1.396(2) . ?
C11 C16 1.402(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 C17 1.503(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O1 C1 C2 115.46(15) . . ?
O1 C1 C9 123.42(14) . . ?
C2 C1 C9 121.10(16) . . ?
C1 C2 C3 121.31(16) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.06(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C10 120.49(16) . . ?
C3 C4 H4 119.8 . . ?
C10 C4 H4 119.8 . . ?
C6 C5 C10 120.92(16) . . ?
C6 C5 H5 119.5 . . ?
C10 C5 H5 119.5 . . ?
C5 C6 C7 119.77(16) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 121.87(16) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 119.41(15) . . ?
C7 C8 C11 116.79(14) . . ?
C9 C8 C11 123.79(14) . . ?
C8 C9 C10 118.75(14) . . ?
C8 C9 C1 125.15(15) . . ?
C10 C9 C1 116.07(14) . . ?
C4 C10 C5 119.79(16) . . ?
C4 C10 C9 120.95(15) . . ?
C5 C10 C9 119.26(15) . . ?
C12 C11 C16 117.60(15) . . ?
C12 C11 C8 120.24(14) . . ?
C16 C11 C8 122.07(14) . . ?
C13 C12 C11 120.98(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.34(15) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 117.88(15) . . ?
C15 C14 C17 121.80(16) . . ?
C13 C14 C17 120.32(16) . . ?
C16 C15 C14 120.96(15) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 121.23(16) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 O1 H1 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.47
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.270
_refine_diff_density_min   -0.284
_refine_diff_density_rms    0.059
