 
data_2007may0002
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H10 O3'
_chemical_formula_weight          166.17
 
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            Tetragonal
_symmetry_space_group_name_H-M    I4(1)/a
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-y+3/4, x+1/4, z+1/4'
 'y+3/4, -x+3/4, z+3/4'
 'x+1/2, y+1/2, z+1/2'
 '-x+1, -y+1/2, z+1'
 '-y+5/4, x+3/4, z+3/4'
 'y+5/4, -x+5/4, z+5/4'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'y-3/4, -x-1/4, -z-1/4'
 '-y-3/4, x-3/4, -z-3/4'
 '-x+1/2, -y+1/2, -z+1/2'
 'x, y+1/2, -z'
 'y-1/4, -x+1/4, -z+1/4'
 '-y-1/4, x-1/4, -z-1/4'
 
_cell_length_a                    22.5496(4)
_cell_length_b                    22.5496(4)
_cell_length_c                    6.3581(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3233.00(13)
_cell_formula_units_Z             16
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6355
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut rod'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.366
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1408
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9699
_exptl_absorpt_correction_T_max   0.9878
_exptl_absorpt_process_details    
'SADABS 2007/2 (Sheldrick, G.M., 2007)'
 
_exptl_special_details
;
The values for Tmin and Tmax are based on cell
dimensions only and were generated using the size 
command in SHELX. SADABS estimates the minimum and maximum 
transmission as 0.5945 and 0.7456, respectively. 
;
 
_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             13180
_diffrn_reflns_av_R_equivalents   0.0690
_diffrn_reflns_av_sigmaI/netI     0.0530
_diffrn_reflns_limit_h_min        -28
_diffrn_reflns_limit_h_max        29
_diffrn_reflns_limit_k_min        -29
_diffrn_reflns_limit_k_max        29
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        7
_diffrn_reflns_theta_min          3.33
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1858
_reflns_number_gt                 1345
_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, 1997)'
_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)+(0.0509P)²+1.9821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0019(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1858
_refine_ls_number_parameters      114
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0720
_refine_ls_R_factor_gt            0.0467
_refine_ls_wR_factor_ref          0.1221
_refine_ls_wR_factor_gt           0.1089
_refine_ls_goodness_of_fit_ref    1.052
_refine_ls_restrained_S_all       1.052
_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 0.28376(8) 0.37356(8) 0.4042(3) 0.0269(4) Uani 1 1 d . . .
H1A H 0.3256 0.3818 0.4412 0.032 Uiso 1 1 calc R . .
H1B H 0.2614 0.4112 0.4130 0.032 Uiso 1 1 calc R . .
C2 C 0.28035(7) 0.34934(7) 0.1833(3) 0.0228(4) Uani 1 1 d . . .
H2 H 0.2992 0.3092 0.1815 0.027 Uiso 1 1 calc R . .
C3 C 0.18549(7) 0.31455(7) 0.2780(3) 0.0213(4) Uani 1 1 d . . .
C4 C 0.13048(7) 0.29167(7) 0.2232(3) 0.0265(4) Uani 1 1 d . . .
H4 H 0.1158 0.2971 0.0845 0.032 Uiso 1 1 calc R . .
C5 C 0.09690(8) 0.26098(8) 0.3694(3) 0.0300(4) Uani 1 1 d . . .
H5 H 0.0593 0.2453 0.3308 0.036 Uiso 1 1 calc R . .
C6 C 0.11819(8) 0.25309(8) 0.5726(3) 0.0309(4) Uani 1 1 d . . .
H6 H 0.0955 0.2313 0.6720 0.037 Uiso 1 1 calc R . .
C7 C 0.17237(8) 0.27692(7) 0.6304(3) 0.0272(4) Uani 1 1 d . . .
H7 H 0.1867 0.2718 0.7697 0.033 Uiso 1 1 calc R . .
C8 C 0.20580(7) 0.30840(7) 0.4843(3) 0.0222(4) Uani 1 1 d . . .
C9 C 0.31006(8) 0.38731(7) 0.0188(3) 0.0255(4) Uani 1 1 d . . .
H9A H 0.3532 0.3883 0.0471 0.031 Uiso 1 1 calc R . .
H9B H 0.3042 0.3688 -0.1209 0.031 Uiso 1 1 calc R . .
O1 O 0.25925(5) 0.33117(5) 0.54950(18) 0.0281(3) Uani 1 1 d . . .
O2 O 0.21848(5) 0.34293(5) 0.12580(16) 0.0237(3) Uani 1 1 d . . .
O3 O 0.28831(6) 0.44636(5) 0.0123(2) 0.0300(3) Uani 1 1 d . . .
H1O H 0.2566(11) 0.4475(10) -0.067(4) 0.059(7) Uiso 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.0294(9) 0.0301(10) 0.0213(9) 0.0017(7) -0.0011(7) -0.0076(7)
C2 0.0194(8) 0.0251(9) 0.0239(8) -0.0019(7) -0.0011(7) 0.0007(7)
C3 0.0218(8) 0.0179(8) 0.0243(9) -0.0003(6) 0.0030(7) 0.0019(7)
C4 0.0230(9) 0.0262(9) 0.0302(9) -0.0025(7) -0.0014(7) 0.0033(7)
C5 0.0204(9) 0.0270(9) 0.0424(11) -0.0059(8) 0.0056(8) -0.0008(7)
C6 0.0293(10) 0.0243(9) 0.0392(11) -0.0007(8) 0.0148(8) -0.0007(7)
C7 0.0320(10) 0.0249(9) 0.0247(9) -0.0011(7) 0.0071(7) 0.0034(7)
C8 0.0219(9) 0.0204(8) 0.0243(8) -0.0035(7) 0.0008(7) 0.0022(7)
C9 0.0255(9) 0.0273(9) 0.0237(9) 0.0002(7) -0.0004(7) -0.0017(7)
O1 0.0300(7) 0.0334(7) 0.0207(6) 0.0030(5) -0.0033(5) -0.0080(5)
O2 0.0211(6) 0.0282(7) 0.0218(6) 0.0027(5) -0.0021(5) -0.0031(5)
O3 0.0338(8) 0.0230(7) 0.0331(7) 0.0018(5) -0.0080(6) -0.0040(5)
 
_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 O1 1.440(2) . ?
C1 C2 1.509(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.4494(19) . ?
C2 C9 1.509(2) . ?
C2 H2 1.0000 . ?
C3 O2 1.3782(19) . ?
C3 C4 1.388(2) . ?
C3 C8 1.396(2) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 O1 1.3741(19) . ?
C9 O3 1.420(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O3 H1O 0.87(3) . ?
 
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 109.72(14) . . ?
O1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
O1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
O2 C2 C9 108.01(13) . . ?
O2 C2 C1 108.67(13) . . ?
C9 C2 C1 114.66(14) . . ?
O2 C2 H2 108.4 . . ?
C9 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
O2 C3 C4 118.61(14) . . ?
O2 C3 C8 121.91(14) . . ?
C4 C3 C8 119.47(15) . . ?
C5 C4 C3 120.42(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.95(16) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.14(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.92(16) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O1 C8 C7 117.67(14) . . ?
O1 C8 C3 122.28(14) . . ?
C7 C8 C3 120.02(15) . . ?
O3 C9 C2 113.51(14) . . ?
O3 C9 H9A 108.9 . . ?
C2 C9 H9A 108.9 . . ?
O3 C9 H9B 108.9 . . ?
C2 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C8 O1 C1 113.03(12) . . ?
C3 O2 C2 112.88(12) . . ?
C9 O3 H1O 109.0(16) . . ?
 
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
O3 H1O O3  0.87(3) 1.77(3) 2.6355(14) 171(2) 4_454
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.227
_refine_diff_density_min   -0.178
_refine_diff_density_rms    0.050
