data_04src0995
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. I. R. Butler
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C18 H22 O2'
_chemical_formula_sum
 'C18 H22 O2'
_chemical_formula_weight          270.36
 
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    P2(1)/n
_symmetry_space_group_name_hall   '-P 2yn'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    10.8714(17)
_cell_length_b                    10.9150(8)
_cell_length_c                    13.574(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  111.897(15)
_cell_angle_gamma                 90.00
_cell_volume                      1494.5(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3543
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.26
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.18
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.202
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              584
_exptl_absorpt_coefficient_mu     0.076
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9804
_exptl_absorpt_correction_T_max   0.9864
_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             15320
_diffrn_reflns_av_R_equivalents   0.0329
_diffrn_reflns_av_sigmaI/netI     0.0291
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.55
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3404
_reflns_number_gt                 2986
_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)+(0.0356P)²+0.7484P] 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          3404
_refine_ls_number_parameters      186
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0486
_refine_ls_R_factor_gt            0.0417
_refine_ls_wR_factor_ref          0.1017
_refine_ls_wR_factor_gt           0.0976
_refine_ls_goodness_of_fit_ref    1.041
_refine_ls_restrained_S_all       1.041
_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 0.14816(11) 0.49655(10) 0.37085(9) 0.0157(2) Uani 1 1 d . . .
C2 C 0.00379(11) 0.46191(11) 0.30409(9) 0.0164(2) Uani 1 1 d . . .
C3 C -0.02013(12) 0.35288(11) 0.24572(9) 0.0201(2) Uani 1 1 d . . .
H3 H 0.0525 0.3011 0.2516 0.024 Uiso 1 1 calc R . .
C4 C -0.14631(12) 0.31845(11) 0.17981(9) 0.0212(3) Uani 1 1 d . . .
H4 H -0.1600 0.2439 0.1410 0.025 Uiso 1 1 calc R . .
C5 C -0.25284(11) 0.39354(11) 0.17071(9) 0.0185(2) Uani 1 1 d . . .
C6 C -0.23320(11) 0.49985(11) 0.23004(9) 0.0186(2) Uani 1 1 d . . .
H6 H -0.3066 0.5497 0.2259 0.022 Uiso 1 1 calc R . .
C7 C -0.10520(11) 0.53356(11) 0.29593(9) 0.0174(2) Uani 1 1 d . . .
H7 H -0.0922 0.6070 0.3361 0.021 Uiso 1 1 calc R . .
C8 C 0.22539(11) 0.49897(10) 0.29659(9) 0.0157(2) Uani 1 1 d . . .
C9 C 0.34781(11) 0.44259(11) 0.32033(9) 0.0193(2) Uani 1 1 d . . .
H9 H 0.3843 0.3955 0.3835 0.023 Uiso 1 1 calc R . .
C10 C 0.41808(12) 0.45373(12) 0.25348(9) 0.0213(3) Uani 1 1 d . . .
H10 H 0.5022 0.4155 0.2716 0.026 Uiso 1 1 calc R . .
C11 C 0.36506(11) 0.52049(11) 0.16075(9) 0.0188(2) Uani 1 1 d . . .
C12 C 0.24151(11) 0.57473(11) 0.13330(9) 0.0186(2) Uani 1 1 d . . .
H12 H 0.2037 0.6187 0.0686 0.022 Uiso 1 1 calc R . .
C13 C 0.17381(11) 0.56402(11) 0.20139(9) 0.0177(2) Uani 1 1 d . . .
H13 H 0.0896 0.6021 0.1827 0.021 Uiso 1 1 calc R . .
C14 C 0.20154(12) 0.39912(11) 0.45836(9) 0.0202(2) Uani 1 1 d . . .
H14A H 0.1986 0.3185 0.4258 0.030 Uiso 1 1 calc R . .
H14B H 0.1468 0.3980 0.5016 0.030 Uiso 1 1 calc R . .
H14C H 0.2933 0.4188 0.5034 0.030 Uiso 1 1 calc R . .
C15 C 0.15571(11) 0.62358(11) 0.42346(9) 0.0178(2) Uani 1 1 d . . .
H15A H 0.1152 0.6843 0.3663 0.021 Uiso 1 1 calc R . .
H15B H 0.0999 0.6206 0.4667 0.021 Uiso 1 1 calc R . .
C16 C 0.29319(12) 0.67201(11) 0.49457(9) 0.0209(3) Uani 1 1 d . . .
H16 H 0.3473 0.6012 0.5346 0.025 Uiso 1 1 calc R . .
C17 C 0.27657(14) 0.76201(13) 0.57453(11) 0.0309(3) Uani 1 1 d . . .
H17A H 0.3638 0.7925 0.6209 0.046 Uiso 1 1 calc R . .
H17B H 0.2340 0.7205 0.6175 0.046 Uiso 1 1 calc R . .
H17C H 0.2212 0.8309 0.5366 0.046 Uiso 1 1 calc R . .
C18 C 0.36884(13) 0.73434(12) 0.43336(11) 0.0266(3) Uani 1 1 d . . .
H18A H 0.3147 0.8006 0.3897 0.040 Uiso 1 1 calc R . .
H18B H 0.3882 0.6742 0.3875 0.040 Uiso 1 1 calc R . .
H18C H 0.4521 0.7682 0.4836 0.040 Uiso 1 1 calc R . .
O5 O -0.37610(8) 0.35890(8) 0.09880(7) 0.0230(2) Uani 1 1 d . . .
H5 H -0.4339 0.4079 0.1024 0.034 Uiso 1 1 calc R . .
O11 O 0.43862(8) 0.52844(9) 0.09738(7) 0.0249(2) Uani 1 1 d . . .
H11 H 0.3997 0.5744 0.0454 0.037 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 C8 1.5339(15) . ?
C1 C14 1.5377(16) . ?
C1 C2 1.5384(16) . ?
C1 C15 1.5478(16) . ?
C2 C7 1.3892(16) . ?
C2 C3 1.3992(16) . ?
C3 C4 1.3813(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3863(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3828(17) . ?
C5 O5 1.3841(14) . ?
C6 C7 1.3941(16) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.3906(16) . ?
C8 C13 1.3957(16) . ?
C9 C10 1.3924(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3807(17) . ?
C10 H10 0.9500 . ?
C11 O11 1.3784(14) . ?
C11 C12 1.3857(16) . ?
C12 C13 1.3846(16) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.5392(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5237(18) . ?
C16 C18 1.5295(17) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O5 H5 0.8400 . ?
O11 H11 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
C8 C1 C14 112.22(9) . . ?
C8 C1 C2 107.78(9) . . ?
C14 C1 C2 107.05(9) . . ?
C8 C1 C15 109.88(9) . . ?
C14 C1 C15 108.86(9) . . ?
C2 C1 C15 111.03(9) . . ?
C7 C2 C3 117.44(11) . . ?
C7 C2 C1 124.13(10) . . ?
C3 C2 C1 118.42(10) . . ?
C4 C3 C2 121.88(11) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.45(11) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 O5 122.58(11) . . ?
C6 C5 C4 120.12(11) . . ?
O5 C5 C4 117.27(11) . . ?
C5 C6 C7 119.70(11) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 121.34(11) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C9 C8 C13 117.32(10) . . ?
C9 C8 C1 123.45(10) . . ?
C13 C8 C1 119.20(10) . . ?
C8 C9 C10 121.38(11) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 119.75(11) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
O11 C11 C10 117.39(10) . . ?
O11 C11 C12 122.35(11) . . ?
C10 C11 C12 120.26(11) . . ?
C13 C12 C11 119.19(11) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 122.07(10) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C1 117.97(9) . . ?
C16 C15 H15A 107.8 . . ?
C1 C15 H15A 107.8 . . ?
C16 C15 H15B 107.8 . . ?
C1 C15 H15B 107.8 . . ?
H15A C15 H15B 107.2 . . ?
C17 C16 C18 109.32(11) . . ?
C17 C16 C15 108.83(10) . . ?
C18 C16 C15 113.90(10) . . ?
C17 C16 H16 108.2 . . ?
C18 C16 H16 108.2 . . ?
C15 C16 H16 108.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 O5 H5 109.5 . . ?
C11 O11 H11 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
O5 H5 O11  0.84 1.89 2.7300(13) 173.4 1_455
O11 H11 O5  0.84 2.01 2.7777(13) 150.9 3_565
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.309
_refine_diff_density_min   -0.208
_refine_diff_density_rms    0.040
