 
data_2007may0017
 
_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   0.0000
 '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    Pna2(1)
 
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'
 
_cell_length_a                    7.8484(6)
_cell_length_b                    8.3983(7)
_cell_length_c                    24.1255(18)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1590.2(2)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     61666
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut shard'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.388
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              704
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9896
_exptl_absorpt_correction_T_max   0.9979
_exptl_absorpt_process_details    
'SADABS 2007/2 (Sheldrick, G.M., 2007)' 
 
_exptl_special_details
;
The values of Tmin and Tmax are based on the cell
dimensions only and were generated using the size 
command in SHELX. SADABS reports the ratio of minimum 
to maximum apparent transmission as 0.602185
;
 
_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 APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             15676
_diffrn_reflns_av_R_equivalents   0.0666
_diffrn_reflns_av_sigmaI/netI     0.0418
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -31
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          3.38
_diffrn_reflns_theta_max          27.50
_reflns_number_total              1831
_reflns_number_gt                 1548
_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)+(0.1420P)²+2.6350P] 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      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          1831
_refine_ls_number_parameters      225
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.1106
_refine_ls_R_factor_gt            0.0938
_refine_ls_wR_factor_ref          0.2736
_refine_ls_wR_factor_gt           0.2549
_refine_ls_goodness_of_fit_ref    1.123
_refine_ls_restrained_S_all       1.122
_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 -0.0061(10) 0.0747(8) 0.2662(3) 0.0391(16) Uani 1 1 d . . .
H1A H 0.0799 0.1496 0.2811 0.047 Uiso 1 1 calc R . .
H1B H -0.1201 0.1143 0.2771 0.047 Uiso 1 1 calc R . .
C2 C 0.0060(9) 0.0724(7) 0.2037(3) 0.0339(15) Uani 1 1 d . . .
C3 C 0.1458(10) 0.1411(8) 0.1766(3) 0.0383(16) Uani 1 1 d . . .
H3 H 0.2343 0.1893 0.1976 0.046 Uiso 1 1 calc R . .
C4 C 0.1552(10) 0.1389(8) 0.1191(4) 0.049(2) Uani 1 1 d . . .
H4 H 0.2497 0.1865 0.1009 0.059 Uiso 1 1 calc R . .
C5 C 0.0283(11) 0.0684(8) 0.0884(3) 0.0426(18) Uani 1 1 d . . .
H5 H 0.0342 0.0694 0.0490 0.051 Uiso 1 1 calc R . .
C6 C -0.1080(10) -0.0042(7) 0.1148(3) 0.0380(16) Uani 1 1 d . . .
C7 C -0.3463(12) -0.1711(12) 0.1120(4) 0.063(3) Uani 1 1 d . . .
H7A H -0.2942 -0.2757 0.1204 0.076 Uiso 1 1 calc R . .
H7B H -0.4480 -0.1901 0.0886 0.076 Uiso 1 1 calc R . .
C8 C -0.4001(12) -0.0957(12) 0.1642(4) 0.057(2) Uani 1 1 d . . .
H8A H -0.4578 0.0064 0.1560 0.068 Uiso 1 1 calc R . .
H8B H -0.4826 -0.1658 0.1834 0.068 Uiso 1 1 calc R . .
C9 C -0.1187(10) -0.0010(8) 0.1721(3) 0.0353(16) Uani 1 1 d . . .
O1 O 0.0206(7) -0.0800(5) 0.2904(2) 0.0415(12) Uani 1 1 d D . .
O2 O -0.2275(7) -0.0771(6) 0.0818(2) 0.0427(13) Uani 1 1 d . . .
O3 O -0.2553(6) -0.0666(6) 0.2001(2) 0.0392(12) Uani 1 1 d . . .
H1O H 0.120(6) -0.096(12) 0.279(4) 0.07(3) Uiso 1 1 d D . .
C10 C 0.4717(11) -0.0450(9) 0.3096(3) 0.0421(18) Uani 1 1 d . . .
H10A H 0.4520 0.0672 0.2986 0.051 Uiso 1 1 calc R . .
H10B H 0.5878 -0.0745 0.2972 0.051 Uiso 1 1 calc R . .
C11 C 0.4643(9) -0.0562(7) 0.3720(3) 0.0345(15) Uani 1 1 d . . .
C12 C 0.3359(9) -0.1355(9) 0.4007(3) 0.0426(18) Uani 1 1 d . . .
H12 H 0.2456 -0.1841 0.3807 0.051 Uiso 1 1 calc R . .
C13 C 0.3373(10) -0.1449(9) 0.4579(3) 0.0431(17) Uani 1 1 d . . .
H13 H 0.2475 -0.1982 0.4767 0.052 Uiso 1 1 calc R . .
C14 C 0.4676(10) -0.0775(8) 0.4877(3) 0.0401(17) Uani 1 1 d . . .
H14 H 0.4690 -0.0859 0.5270 0.048 Uiso 1 1 calc R . .
C15 C 0.5970(8) 0.0027(7) 0.4605(3) 0.0339(15) Uani 1 1 d . . .
C16 C 0.8355(10) 0.1759(10) 0.4617(3) 0.0433(17) Uani 1 1 d . . .
H16A H 0.9427 0.1914 0.4826 0.052 Uiso 1 1 calc R . .
H16B H 0.7807 0.2811 0.4568 0.052 Uiso 1 1 calc R . .
C17 C 0.8740(9) 0.1047(9) 0.4061(3) 0.0423(17) Uani 1 1 d . . .
H17A H 0.9575 0.1725 0.3864 0.051 Uiso 1 1 calc R . .
H17B H 0.9253 -0.0020 0.4112 0.051 Uiso 1 1 calc R . .
C18 C 0.5948(9) 0.0129(8) 0.4022(3) 0.0335(15) Uani 1 1 d . . .
O4 O 0.3524(7) -0.1426(5) 0.2815(2) 0.0415(12) Uani 1 1 d D . .
O5 O 0.7233(7) 0.0714(6) 0.4922(2) 0.0435(13) Uani 1 1 d . . .
O6 O 0.7233(6) 0.0914(6) 0.3740(2) 0.0387(12) Uani 1 1 d . . .
H2O H 0.382(12) -0.239(4) 0.284(5) 0.07(3) Uiso 1 1 d D . .
 
 
_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(8) . ?
C1 C2 1.510(11) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C9 1.385(10) . ?
C2 C3 1.402(9) . ?
C3 C4 1.390(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(11) . ?
C5 H5 0.9500 . ?
C6 O2 1.374(10) . ?
C6 C9 1.386(10) . ?
C7 O2 1.422(10) . ?
C7 C8 1.471(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O3 1.450(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O3 1.382(9) . ?
O1 H1O 0.84(2) . ?
C10 O4 1.417(9) . ?
C10 C11 1.510(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.384(10) . ?
C11 C12 1.393(10) . ?
C12 C13 1.381(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(10) . ?
C14 H14 0.9500 . ?
C15 O5 1.378(9) . ?
C15 C18 1.410(10) . ?
C16 O5 1.445(9) . ?
C16 C17 1.497(11) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O6 1.419(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O6 1.383(9) . ?
O4 H2O 0.84(2) . ?
 
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 112.6(6) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C9 C2 C3 118.7(7) . . ?
C9 C2 C1 120.7(7) . . ?
C3 C2 C1 120.6(7) . . ?
C4 C3 C2 120.1(7) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.4(7) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.0(8) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
O2 C6 C9 123.0(7) . . ?
O2 C6 C5 117.2(7) . . ?
C9 C6 C5 119.8(7) . . ?
O2 C7 C8 112.8(8) . . ?
O2 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
O2 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O3 C8 C7 111.0(8) . . ?
O3 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
O3 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O3 C9 C2 117.2(6) . . ?
O3 C9 C6 121.8(7) . . ?
C2 C9 C6 121.0(7) . . ?
C1 O1 H1O 99(7) . . ?
C6 O2 C7 113.5(6) . . ?
C9 O3 C8 112.6(6) . . ?
O4 C10 C11 114.6(6) . . ?
O4 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
O4 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C18 C11 C12 118.3(7) . . ?
C18 C11 C10 118.0(6) . . ?
C12 C11 C10 123.6(7) . . ?
C13 C12 C11 121.2(7) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 120.4(7) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.9(7) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
O5 C15 C14 117.9(7) . . ?
O5 C15 C18 122.4(6) . . ?
C14 C15 C18 119.6(7) . . ?
O5 C16 C17 109.6(6) . . ?
O5 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
O5 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O6 C17 C16 110.6(6) . . ?
O6 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
O6 C18 C11 118.7(7) . . ?
O6 C18 C15 120.7(6) . . ?
C11 C18 C15 120.5(6) . . ?
C10 O4 H2O 109(7) . . ?
C15 O5 C16 114.2(6) . . ?
C18 O6 C17 112.1(6) . . ?
 
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
O4 H2O O1  0.84(2) 1.88(4) 2.686(7) 161(9) 3_545
O1 H1O O4  0.84(2) 1.87(5) 2.665(7) 159(11) .
 
_diffrn_measured_fraction_theta_max    0.981
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.981
_refine_diff_density_max    0.495
_refine_diff_density_min   -0.382
_refine_diff_density_rms    0.085
