 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H22 O2'
_chemical_formula_weight          210.31
 
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    P21/n
 
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                    8.9541(2)
_cell_length_b                    7.1843(2)
_cell_length_c                    19.1662(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  98.1620(10)
_cell_angle_gamma                 90.00
_cell_volume                      1220.45(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     9801
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       32.58
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.145
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              464
_exptl_absorpt_coefficient_mu     0.075
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9806
_exptl_absorpt_correction_T_max   0.9970
_exptl_absorpt_process_details    
'SADABS V2.10 (Sheldrick, 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       296(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 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             4854
_diffrn_reflns_av_R_equivalents   0.0571
_diffrn_reflns_av_sigmaI/netI     0.0790
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.03
_diffrn_reflns_theta_max          25.50
_reflns_number_total              2160
_reflns_number_gt                 1280
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0495P)²+0.0000P] 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          2160
_refine_ls_number_parameters      160
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1003
_refine_ls_R_factor_gt            0.0490
_refine_ls_wR_factor_ref          0.1134
_refine_ls_wR_factor_gt           0.1011
_refine_ls_goodness_of_fit_ref    0.945
_refine_ls_restrained_S_all       0.945
_refine_ls_shift/su_max           0.001
_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
O1 O 0.34516(13) 0.67407(15) 0.18947(6) 0.0397(4) Uani 1 1 d . . .
H1O H 0.3221 0.5644 0.1829 0.087(8) Uiso 1 1 calc R . .
O2 O 0.25388(14) 1.30053(14) 0.18670(8) 0.0520(4) Uani 1 1 d . . .
H2O H 0.2352 1.2655 0.2252 0.097(9) Uiso 1 1 calc R . .
C1 C 0.38516(18) 0.7525(2) 0.12545(9) 0.0328(4) Uani 1 1 d . . .
C2 C 0.23953(19) 0.8421(2) 0.08391(9) 0.0394(5) Uani 1 1 d . . .
C3 C 0.1873(2) 1.0008(2) 0.12739(9) 0.0375(5) Uani 1 1 d . . .
C4 C 0.3063(2) 1.1470(2) 0.14977(10) 0.0408(5) Uani 1 1 d . . .
H4 H 0.3376 1.1971 0.1065 0.039(5) Uiso 1 1 calc R . .
C5 C 0.4444(2) 1.0560(2) 0.19106(10) 0.0410(5) Uani 1 1 d . . .
H5A H 0.4180 1.0051 0.2346 0.037(5) Uiso 1 1 calc R . .
H5B H 0.5220 1.1493 0.2032 0.051(5) Uiso 1 1 calc R . .
C6 C 0.50584(19) 0.9016(2) 0.14914(10) 0.0380(5) Uani 1 1 d . . .
H6 H 0.5328 0.9588 0.1062 0.037(5) Uiso 1 1 calc R . .
C7 C 0.6503(2) 0.8167(3) 0.18843(11) 0.0506(6) Uani 1 1 d . . .
H7A H 0.7250 0.9141 0.1994 0.069(6) Uiso 1 1 calc R . .
H7B H 0.6291 0.7639 0.2325 0.048(5) Uiso 1 1 calc R . .
C8 C 0.7143(2) 0.6664(3) 0.14558(12) 0.0557(6) Uani 1 1 d . . .
H8A H 0.7453 0.7209 0.1036 0.061(6) Uiso 1 1 calc R . .
H8B H 0.8024 0.6112 0.1732 0.057(6) Uiso 1 1 calc R . .
C9 C 0.5965(2) 0.5176(2) 0.12475(12) 0.0535(6) Uani 1 1 d . . .
H9A H 0.5717 0.4564 0.1667 0.056(6) Uiso 1 1 calc R . .
H9B H 0.6369 0.4247 0.0958 0.063(6) Uiso 1 1 calc R . .
C10 C 0.4544(2) 0.6022(2) 0.08398(10) 0.0436(5) Uani 1 1 d . . .
H10A H 0.3806 0.5044 0.0717 0.037(4) Uiso 1 1 calc R . .
H10B H 0.4787 0.6555 0.0405 0.048(5) Uiso 1 1 calc R . .
C11 C 0.1162(2) 0.6933(3) 0.06737(13) 0.0614(6) Uani 1 1 d . . .
H11A H 0.1508 0.5980 0.0384 0.061(6) Uiso 1 1 calc R . .
H11B H 0.0266 0.7497 0.0428 0.066(6) Uiso 1 1 calc R . .
H11C H 0.0940 0.6393 0.1106 0.073(8) Uiso 1 1 calc R . .
C12 C 0.2689(3) 0.9229(3) 0.01225(10) 0.0578(6) Uani 1 1 d . . .
H12A H 0.2905 0.8233 -0.0182 0.075(7) Uiso 1 1 calc R . .
H12B H 0.3534 1.0064 0.0196 0.091(9) Uiso 1 1 calc R . .
H12C H 0.1811 0.9892 -0.0092 0.094(8) Uiso 1 1 calc R . .
C13 C 0.0515(3) 1.0149(3) 0.14564(12) 0.0586(6) Uani 1 1 d . . .
H13B H 0.0277 1.1154 0.1726 0.055(6) Uiso 1 1 calc R . .
H13A H -0.0207 0.9243 0.1316 0.058(6) 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
O1 C1 1.4410(17) . ?
O1 H1O 0.8200 . ?
O2 C4 1.4253(18) . ?
O2 H2O 0.8200 . ?
C1 C10 1.524(2) . ?
C1 C6 1.543(2) . ?
C1 C2 1.566(2) . ?
C2 C3 1.524(2) . ?
C2 C11 1.538(2) . ?
C2 C12 1.548(2) . ?
C3 C13 1.316(2) . ?
C3 C4 1.514(2) . ?
C4 C5 1.518(2) . ?
C4 H4 0.9800 . ?
C5 C6 1.518(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.528(2) . ?
C6 H6 0.9800 . ?
C7 C8 1.517(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.516(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.522(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13B 0.9300 . ?
C13 H13A 0.9300 . ?
 
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
C1 O1 H1O 109.5 . . ?
C4 O2 H2O 109.5 . . ?
O1 C1 C10 109.60(13) . . ?
O1 C1 C6 105.62(13) . . ?
C10 C1 C6 109.00(13) . . ?
O1 C1 C2 107.69(12) . . ?
C10 C1 C2 113.40(14) . . ?
C6 C1 C2 111.22(13) . . ?
C3 C2 C11 111.45(15) . . ?
C3 C2 C12 107.97(14) . . ?
C11 C2 C12 106.59(17) . . ?
C3 C2 C1 109.10(14) . . ?
C11 C2 C1 109.94(14) . . ?
C12 C2 C1 111.77(15) . . ?
C13 C3 C4 120.72(18) . . ?
C13 C3 C2 124.70(17) . . ?
C4 C3 C2 114.57(15) . . ?
O2 C4 C3 114.17(15) . . ?
O2 C4 C5 112.06(15) . . ?
C3 C4 C5 109.70(13) . . ?
O2 C4 H4 106.8 . . ?
C3 C4 H4 106.8 . . ?
C5 C4 H4 106.8 . . ?
C4 C5 C6 111.62(15) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 112.08(15) . . ?
C5 C6 C1 111.81(14) . . ?
C7 C6 C1 112.11(14) . . ?
C5 C6 H6 106.8 . . ?
C7 C6 H6 106.8 . . ?
C1 C6 H6 106.8 . . ?
C8 C7 C6 112.07(17) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.02(16) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 C10 110.69(15) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C1 112.81(16) . . ?
C9 C10 H10A 109.0 . . ?
C1 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13B 120.0 . . ?
C3 C13 H13A 120.0 . . ?
H13B C13 H13A 120.0 . . ?
 
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 H1O O2  0.82 2.00 2.8037(15) 168.3 1_545
O2 H2O O1  0.82 1.99 2.8004(18) 170.4 2
 
_diffrn_measured_fraction_theta_max    0.952
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.952
_refine_diff_density_max    0.174
_refine_diff_density_min   -0.152
_refine_diff_density_rms    0.037
