 
data_shelx

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            '5-Hydroxyisophthalic Acid-Acetone 1:1 Solvate'
_chemical_formula_moiety         'C8 H6 O5, C3 H6 O'
_chemical_formula_sum            'C11 H12 O6'
_exptl_crystal_recrystallization_method evaporation
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      173(2)
_diffrn_ambient_pressure         101.3
_chemical_formula_weight         240.21

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9655(7)
_cell_length_b                   11.2080(11)
_cell_length_c                   15.6562(16)
_cell_angle_alpha                83.613(3)
_cell_angle_beta                 85.272(3)
_cell_angle_gamma                76.055(2)
_cell_volume                     1176.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11601
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.41
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   'multi-scan'
_exptl_absorpt_correction_T_min  0.7461
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   'abscor Higashi RIGAKU'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'fine-focus rotating anode x-ray'
_diffrn_source_type              RIGAKU
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       'ω-scan'
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11601
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.41
_reflns_number_total             5310
_reflns_number_gt                2546
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO'
_computing_cell_refinement       'RAPID-AUTO'
_computing_data_reduction        'RAPID-AUTO'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0700P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5310
_refine_ls_number_parameters     336
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.996
_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
O1 O -0.1871(3) 0.93817(14) 0.81492(12) 0.0547(5) Uani 1 1 d . . .
H1 H -0.159(4) 0.970(3) 0.757(2) 0.066 Uiso 1 1 d . . .
C2 C -0.1607(3) 0.81385(19) 0.81890(15) 0.0350(5) Uani 1 1 d . . .
C3 C -0.0802(3) 0.74610(19) 0.74975(14) 0.0322(5) Uani 1 1 d . . .
H3 H -0.0437 0.7871 0.6967 0.039 Uiso 1 1 calc R . .
C4 C -0.0532(3) 0.61863(19) 0.75837(13) 0.0287(5) Uani 1 1 d . . .
C5 C 0.0368(3) 0.54913(19) 0.68420(14) 0.0294(5) Uani 1 1 d . . .
O6 O 0.0838(2) 0.60263(14) 0.61541(10) 0.0382(4) Uani 1 1 d . . .
O7 O 0.0609(3) 0.42938(14) 0.69712(10) 0.0423(4) Uani 1 1 d . . .
H7 H 0.142(4) 0.390(2) 0.6508(18) 0.051 Uiso 1 1 d . . .
C8 C -0.1073(3) 0.5570(2) 0.83563(14) 0.0305(5) Uani 1 1 d . . .
H8 H -0.0883 0.4697 0.8414 0.037 Uiso 1 1 calc R . .
C9 C -0.1895(3) 0.6254(2) 0.90384(13) 0.0296(5) Uani 1 1 d . . .
C10 C -0.2509(3) 0.5600(2) 0.98581(14) 0.0319(5) Uani 1 1 d . . .
O11 O -0.2300(3) 0.44472(14) 0.98971(10) 0.0433(4) Uani 1 1 d . . .
O12 O -0.3215(3) 0.62442(15) 1.04884(11) 0.0438(5) Uani 1 1 d . . .
H12 H -0.352(4) 0.574(2) 1.0984(18) 0.053 Uiso 1 1 d . . .
C13 C -0.2166(3) 0.7528(2) 0.89590(14) 0.0340(5) Uani 1 1 d . . .
H13 H -0.2734 0.7984 0.9431 0.041 Uiso 1 1 calc R . .
O14 O 0.5907(3) -0.00720(15) 0.37206(11) 0.0482(5) Uani 1 1 d . . .
H14 H 0.660(4) -0.042(3) 0.3289(19) 0.058 Uiso 1 1 d . . .
C15 C 0.5493(3) 0.1181(2) 0.36036(15) 0.0363(5) Uani 1 1 d . . .
C16 C 0.6011(3) 0.1835(2) 0.28418(14) 0.0332(5) Uani 1 1 d . . .
H16 H 0.6687 0.1401 0.2375 0.040 Uiso 1 1 calc R . .
C17 C 0.5540(3) 0.3118(2) 0.27649(14) 0.0307(5) Uani 1 1 d . . .
C18 C 0.6045(3) 0.3810(2) 0.19414(14) 0.0310(5) Uani 1 1 d . . .
O19 O 0.5746(2) 0.49705(15) 0.19058(10) 0.0435(4) Uani 1 1 d . . .
O20 O 0.6772(2) 0.31757(16) 0.13083(10) 0.0413(4) Uani 1 1 d . . .
H20 H 0.703(4) 0.367(2) 0.0822(18) 0.050 Uiso 1 1 d . . .
C21 C 0.4571(3) 0.3773(2) 0.34405(14) 0.0311(5) Uani 1 1 d . . .
H21 H 0.4268 0.4650 0.3388 0.037 Uiso 1 1 calc R . .
C22 C 0.4050(3) 0.3111(2) 0.41997(13) 0.0303(5) Uani 1 1 d . . .
C23 C 0.2993(3) 0.3783(2) 0.49334(14) 0.0332(5) Uani 1 1 d . . .
O24 O 0.2562(3) 0.32332(14) 0.56198(10) 0.0431(4) Uani 1 1 d . . .
O25 O 0.2581(3) 0.49871(15) 0.47947(10) 0.0429(4) Uani 1 1 d . . .
H25 H 0.191(4) 0.534(2) 0.5264(18) 0.051 Uiso 1 1 d . . .
C26 C 0.4491(3) 0.1831(2) 0.42820(14) 0.0339(5) Uani 1 1 d . . .
H26 H 0.4112 0.1396 0.4799 0.041 Uiso 1 1 calc R . .
C27 C -0.3053(5) 1.2148(3) 0.6732(2) 0.0778(10) Uani 1 1 d . . .
H27A H -0.3357 1.1754 0.7302 0.117 Uiso 1 1 calc R . .
H27B H -0.4272 1.2443 0.6424 0.117 Uiso 1 1 calc R . .
H27C H -0.2480 1.2847 0.6799 0.117 Uiso 1 1 calc R . .
C28 C -0.1617(4) 1.1241(3) 0.62379(19) 0.0563(8) Uani 1 1 d . . .
C29 C -0.0938(6) 1.1668(3) 0.5350(2) 0.0842(12) Uani 1 1 d . . .
H29A H 0.0014 1.0985 0.5099 0.126 Uiso 1 1 calc R . .
H29B H -0.0304 1.2353 0.5378 0.126 Uiso 1 1 calc R . .
H29C H -0.2080 1.1947 0.4992 0.126 Uiso 1 1 calc R . .
O30 O -0.1005(3) 1.01771(17) 0.65347(13) 0.0637(6) Uani 1 1 d . . .
C31 C 1.0237(5) -0.1856(3) 0.1145(2) 0.0753(10) Uani 1 1 d . A .
H31A H 0.9875 -0.2354 0.0736 0.113 Uiso 1 1 calc R . .
H31B H 1.1087 -0.2398 0.1569 0.113 Uiso 1 1 calc R . .
H31C H 1.0953 -0.1271 0.0835 0.113 Uiso 1 1 calc R . .
C32 C 0.8396(5) -0.1158(3) 0.1599(2) 0.0616(8) Uani 1 1 d D . .
C33A C 0.659(2) -0.055(2) 0.1119(9) 0.106(5) Uani 0.64(4) 1 d PD A 1
H33A H 0.5546 -0.0140 0.1520 0.159 Uiso 0.64(4) 1 calc PR A 1
H33B H 0.6132 -0.1166 0.0850 0.159 Uiso 0.64(4) 1 calc PR A 1
H33C H 0.6921 0.0072 0.0673 0.159 Uiso 0.64(4) 1 calc PR A 1
C33B C 0.736(5) -0.0133(18) 0.0982(10) 0.086(6) Uani 0.36(4) 1 d PD A 2
H33D H 0.6149 0.0331 0.1270 0.129 Uiso 0.36(4) 1 calc PR A 2
H33E H 0.7010 -0.0479 0.0484 0.129 Uiso 0.36(4) 1 calc PR A 2
H33F H 0.8235 0.0421 0.0789 0.129 Uiso 0.36(4) 1 calc PR A 2
O34 O 0.8245(3) -0.12179(19) 0.23817(15) 0.0727(7) Uani 1 1 d . A .


_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 C2 1.356(3) . ?
O1 H1 0.95(3) . ?
C2 C3 1.393(3) . ?
C2 C13 1.393(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C8 1.395(3) . ?
C4 C5 1.481(3) . ?
C5 O6 1.233(2) . ?
C5 O7 1.307(2) . ?
O7 H7 0.96(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C13 1.387(3) . ?
C9 C10 1.490(3) . ?
C10 O11 1.259(2) . ?
C10 O12 1.283(3) . ?
O12 H12 0.95(3) . ?
C13 H13 0.9500 . ?
O14 C15 1.359(3) . ?
O14 H14 0.87(3) . ?
C15 C26 1.397(3) . ?
C15 C16 1.397(3) . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 C21 1.389(3) . ?
C17 C18 1.490(3) . ?
C18 O19 1.262(3) . ?
C18 O20 1.283(3) . ?
O20 H20 0.92(3) . ?
C21 C22 1.399(3) . ?
C21 H21 0.9500 . ?
C22 C26 1.387(3) . ?
C22 C23 1.488(3) . ?
C23 O24 1.230(2) . ?
C23 O25 1.308(3) . ?
O25 H25 0.91(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.480(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O30 1.218(3) . ?
C28 C29 1.495(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 C32 1.500(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 O34 1.217(4) . ?
C32 C33A 1.496(7) . ?
C32 C33B 1.498(9) . ?
C33A H33A 0.9800 . ?
C33A H33B 0.9800 . ?
C33A H33C 0.9800 . ?
C33B H33D 0.9800 . ?
C33B H33E 0.9800 . ?
C33B H33F 0.9800 . ?

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
C2 O1 H1 109.5(17) . . ?
O1 C2 C3 122.72(19) . . ?
O1 C2 C13 117.85(19) . . ?
C3 C2 C13 119.43(19) . . ?
C4 C3 C2 120.00(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C8 120.72(19) . . ?
C3 C4 C5 118.62(17) . . ?
C8 C4 C5 120.66(18) . . ?
O6 C5 O7 123.32(19) . . ?
O6 C5 C4 121.23(19) . . ?
O7 C5 C4 115.45(17) . . ?
C5 O7 H7 110.5(14) . . ?
C9 C8 C4 118.87(19) . . ?
C9 C8 H8 120.6 . . ?
C4 C8 H8 120.6 . . ?
C13 C9 C8 120.82(18) . . ?
C13 C9 C10 120.28(18) . . ?
C8 C9 C10 118.90(18) . . ?
O11 C10 O12 123.59(18) . . ?
O11 C10 C9 118.49(18) . . ?
O12 C10 C9 117.92(19) . . ?
C10 O12 H12 111.2(16) . . ?
C9 C13 C2 120.2(2) . . ?
C9 C13 H13 119.9 . . ?
C2 C13 H13 119.9 . . ?
C15 O14 H14 112.8(18) . . ?
O14 C15 C26 117.58(18) . . ?
O14 C15 C16 123.1(2) . . ?
C26 C15 C16 119.3(2) . . ?
C17 C16 C15 120.10(19) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C21 C17 C16 121.04(19) . . ?
C21 C17 C18 119.12(19) . . ?
C16 C17 C18 119.84(19) . . ?
O19 C18 O20 124.00(19) . . ?
O19 C18 C17 118.84(19) . . ?
O20 C18 C17 117.16(19) . . ?
C18 O20 H20 111.8(16) . . ?
C17 C21 C22 118.5(2) . . ?
C17 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C26 C22 C21 121.13(19) . . ?
C26 C22 C23 118.96(18) . . ?
C21 C22 C23 119.91(19) . . ?
O24 C23 O25 123.1(2) . . ?
O24 C23 C22 121.8(2) . . ?
O25 C23 C22 115.14(18) . . ?
C23 O25 H25 110.6(16) . . ?
C22 C26 C15 119.93(18) . . ?
C22 C26 H26 120.0 . . ?
C15 C26 H26 120.0 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O30 C28 C27 121.7(3) . . ?
O30 C28 C29 120.4(3) . . ?
C27 C28 C29 117.8(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O34 C32 C33A 117.9(7) . . ?
O34 C32 C33B 127.2(8) . . ?
C33A C32 C33B 30.5(6) . . ?
O34 C32 C31 120.2(3) . . ?
C33A C32 C31 121.1(6) . . ?
C33B C32 C31 108.6(11) . . ?
C32 C33A H33A 109.5 . . ?
C32 C33A H33B 109.5 . . ?
H33A C33A H33B 109.5 . . ?
C32 C33A H33C 109.5 . . ?
H33A C33A H33C 109.5 . . ?
H33B C33A H33C 109.5 . . ?
C32 C33B H33D 109.5 . . ?
C32 C33B H33E 109.5 . . ?
H33D C33B H33E 109.5 . . ?
C32 C33B H33F 109.5 . . ?
H33D C33B H33F 109.5 . . ?
H33E C33B H33F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 178.7(2) . . . . ?
C13 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C8 0.5(3) . . . . ?
C2 C3 C4 C5 -178.7(2) . . . . ?
C3 C4 C5 O6 -1.4(3) . . . . ?
C8 C4 C5 O6 179.4(2) . . . . ?
C3 C4 C5 O7 178.9(2) . . . . ?
C8 C4 C5 O7 -0.3(3) . . . . ?
C3 C4 C8 C9 0.2(3) . . . . ?
C5 C4 C8 C9 179.4(2) . . . . ?
C4 C8 C9 C13 -0.4(3) . . . . ?
C4 C8 C9 C10 178.8(2) . . . . ?
C13 C9 C10 O11 177.7(2) . . . . ?
C8 C9 C10 O11 -1.5(3) . . . . ?
C13 C9 C10 O12 -2.7(3) . . . . ?
C8 C9 C10 O12 178.1(2) . . . . ?
C8 C9 C13 C2 -0.2(3) . . . . ?
C10 C9 C13 C2 -179.4(2) . . . . ?
O1 C2 C13 C9 -178.9(2) . . . . ?
C3 C2 C13 C9 0.9(4) . . . . ?
O14 C15 C16 C17 179.9(2) . . . . ?
C26 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C21 0.6(3) . . . . ?
C15 C16 C17 C18 -178.2(2) . . . . ?
C21 C17 C18 O19 6.6(3) . . . . ?
C16 C17 C18 O19 -174.6(2) . . . . ?
C21 C17 C18 O20 -173.7(2) . . . . ?
C16 C17 C18 O20 5.2(3) . . . . ?
C16 C17 C21 C22 -0.9(3) . . . . ?
C18 C17 C21 C22 178.0(2) . . . . ?
C17 C21 C22 C26 0.2(3) . . . . ?
C17 C21 C22 C23 -179.4(2) . . . . ?
C26 C22 C23 O24 2.5(3) . . . . ?
C21 C22 C23 O24 -177.8(2) . . . . ?
C26 C22 C23 O25 -178.1(2) . . . . ?
C21 C22 C23 O25 1.6(3) . . . . ?
C21 C22 C26 C15 0.8(3) . . . . ?
C23 C22 C26 C15 -179.6(2) . . . . ?
O14 C15 C26 C22 179.3(2) . . . . ?
C16 C15 C26 C22 -1.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.069

