#==================== 
data_general 
  
_publ_contact_author 
; 
   Prof. Rich Givens 
   Department of Chemistry 
   University of Kansas 
   Rm 2010 Malott Hall 
   1251 Wescoe Hall Dr. 
   Lawrence, KS  66045-7582  USA 
; 
_publ_contact_author_email      givensr@ku.edu 
_publ_contact_author_fax        1(785)8645396 
_publ_contact_author_phone      1(785)8643846 
  
_publ_requested_journal         'journal name here' 
  
loop_ 
    _publ_author_name 
    _publ_author_address 
   'Elizabeth D. Cope' 
;  Department of Chemistry 
   University of Kansas 
   Rm 2010 Malott Hall 
   1251 Wescoe Hall Dr. 
   Lawrence, KS  66045-7582  USA 
; 
  
  'Rich Givens' 
;  Department of Chemistry 
   University of Kansas 
   Rm 2010 Malott Hall 
   1251 Wescoe Hall Dr. 
   Lawrence, KS  66045-7582  USA 
; 
_publ_section_title 
; 
 article title here  'article title here' 
; 
_publ_section_references 
; 
  Bruker (1998) SMART and SAINT, Bruker AXS, Inc., Madison, 
     Wisconsin, USA. 
  
  Sheldrick, G. M. (2000) SADABS, University of Göttingen, 
     Germany 
  
  Sheldrick, G. M. (1997) SHELXTL, Bruker AXS, Inc., Madison, 
     Wisconsin, USA. 
; 
_publ_section_acknowledgements 
; 
 The authors wish to thank the National Science Foundation 
 (CHE-0079282) and the University of Kansas for funds to 
 acquire the diffractometer and computers used in this work. 
; 
    
data_k85d 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C9 H8 O4' 
_chemical_formula_weight          180.15 
  
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)/c 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    8.9605(6) 
_cell_length_b                    8.3220(6) 
_cell_length_c                    10.6750(7) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  98.930(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      786.38(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     3517 
_cell_measurement_theta_min       3.12 
_cell_measurement_theta_max       30.41 
  
_exptl_crystal_description        'Rectangular parallelepiped' 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.21 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.522 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              376 
_exptl_absorpt_coefficient_mu     0.121 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.949 
_exptl_absorpt_correction_T_max   1.000 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker SMART APEX CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0.00 
_diffrn_reflns_number             9794 
_diffrn_reflns_av_R_equivalents   0.0329 
_diffrn_reflns_av_sigmaI/netI     0.0309 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          2.30 
_diffrn_reflns_theta_max          30.50 
_reflns_number_total              2389 
_reflns_number_gt                 1979 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'Bruker SHELXTL' 
_computing_structure_refinement   'Bruker SHELXTL' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_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)+(0.0721P)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          2389 
_refine_ls_number_parameters      150 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0457 
_refine_ls_R_factor_gt            0.0388 
_refine_ls_wR_factor_ref          0.1069 
_refine_ls_wR_factor_gt           0.1037 
_refine_ls_goodness_of_fit_ref    0.988 
_refine_ls_restrained_S_all       0.988 
_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 0.38906(9) 0.12555(9) 0.40415(7) 0.02467(19) Uani 1 1 d . . . 
O2 O 0.51183(9) 0.16730(9) 0.23828(7) 0.02494(19) Uani 1 1 d . . . 
O3 O 0.21680(9) 0.20191(8) 0.56755(8) 0.02361(19) Uani 1 1 d . . . 
O4 O 0.08990(9) 0.93647(9) 0.64338(8) 0.02376(18) Uani 1 1 d . . . 
H4O H 0.1278(17) 1.0059(19) 0.6021(15) 0.040(4) Uiso 1 1 d . . . 
C1 C 0.47189(12) 0.08123(13) 0.31590(10) 0.0232(2) Uani 1 1 d . . . 
H1 H 0.4906(14) -0.0351(17) 0.3247(12) 0.024(3) Uiso 1 1 d . . . 
C2 C 0.34816(12) 0.29250(11) 0.40368(10) 0.0193(2) Uani 1 1 d . . . 
H2A H 0.4402(15) 0.3589(15) 0.4164(13) 0.025(3) Uiso 1 1 d . . . 
H2B H 0.2892(14) 0.3201(14) 0.3219(13) 0.019(3) Uiso 1 1 d . . . 
C3 C 0.25540(10) 0.31734(11) 0.50955(9) 0.0167(2) Uani 1 1 d . . . 
C4 C 0.21498(10) 0.48224(11) 0.53964(9) 0.0162(2) Uani 1 1 d . . . 
C5 C 0.13419(10) 0.50575(11) 0.64101(9) 0.0168(2) Uani 1 1 d . . . 
H5 H 0.1070(13) 0.4131(16) 0.6870(11) 0.022(3) Uiso 1 1 d . . . 
C6 C 0.09348(11) 0.65763(12) 0.67411(9) 0.0180(2) Uani 1 1 d . . . 
H6 H 0.0354(17) 0.6740(17) 0.7461(15) 0.032(4) Uiso 1 1 d . . . 
C7 C 0.13250(11) 0.79018(11) 0.60606(9) 0.0174(2) Uani 1 1 d . . . 
C8 C 0.21120(11) 0.76970(12) 0.50445(9) 0.0180(2) Uani 1 1 d . . . 
H8 H 0.2385(15) 0.8615(17) 0.4587(13) 0.030(4) Uiso 1 1 d . . . 
C9 C 0.25193(11) 0.61676(12) 0.47173(9) 0.0174(2) Uani 1 1 d . . . 
H9 H 0.3018(15) 0.6005(17) 0.3988(13) 0.029(3) 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 
O1 0.0345(4) 0.0152(4) 0.0271(4) 0.0006(3) 0.0135(3) 0.0046(3) 
O2 0.0260(4) 0.0250(4) 0.0254(4) -0.0017(3) 0.0090(3) 0.0002(3) 
O3 0.0297(4) 0.0153(4) 0.0276(4) 0.0020(3) 0.0101(3) -0.0022(3) 
O4 0.0348(4) 0.0123(3) 0.0273(4) 0.0000(3) 0.0147(3) -0.0004(3) 
C1 0.0257(5) 0.0197(5) 0.0249(5) -0.0033(4) 0.0061(4) 0.0026(4) 
C2 0.0242(5) 0.0131(4) 0.0217(5) -0.0006(3) 0.0069(4) 0.0015(3) 
C3 0.0165(4) 0.0154(4) 0.0179(4) -0.0005(3) 0.0021(3) -0.0013(3) 
C4 0.0165(4) 0.0151(4) 0.0171(4) 0.0004(3) 0.0025(3) -0.0015(3) 
C5 0.0179(4) 0.0150(4) 0.0178(4) 0.0026(3) 0.0036(3) -0.0016(3) 
C6 0.0201(4) 0.0171(4) 0.0178(4) 0.0004(3) 0.0062(3) -0.0009(3) 
C7 0.0195(4) 0.0141(4) 0.0190(5) -0.0004(3) 0.0041(3) -0.0005(3) 
C8 0.0214(4) 0.0149(4) 0.0183(4) 0.0018(3) 0.0054(3) -0.0027(3) 
C9 0.0189(4) 0.0172(4) 0.0169(4) 0.0006(3) 0.0051(3) -0.0011(3) 
  
_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 1.3385(12) . ? 
O1 C2 1.4367(12) . ? 
O2 C1 1.1916(13) . ? 
O3 C3 1.2216(12) . ? 
O4 C7 1.3541(11) . ? 
O4 H4O 0.830(17) . ? 
C1 H1 0.984(14) . ? 
C2 C3 1.5173(14) . ? 
C2 H2A 0.984(13) . ? 
C2 H2B 0.975(13) . ? 
C3 C4 1.4675(13) . ? 
C4 C9 1.4011(13) . ? 
C4 C5 1.4059(13) . ? 
C5 C6 1.3768(13) . ? 
C5 H5 0.965(13) . ? 
C6 C7 1.3949(14) . ? 
C6 H6 1.002(16) . ? 
C7 C8 1.3929(14) . ? 
C8 C9 1.3838(13) . ? 
C8 H8 0.958(14) . ? 
C9 H9 0.965(14) . ? 
  
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 C2 115.66(8) . . ? 
C7 O4 H4O 108.2(11) . . ? 
O2 C1 O1 125.66(10) . . ? 
O2 C1 H1 126.3(8) . . ? 
O1 C1 H1 108.0(8) . . ? 
O1 C2 C3 107.34(8) . . ? 
O1 C2 H2A 109.6(7) . . ? 
C3 C2 H2A 111.4(8) . . ? 
O1 C2 H2B 109.5(7) . . ? 
C3 C2 H2B 110.6(7) . . ? 
H2A C2 H2B 108.5(10) . . ? 
O3 C3 C4 121.70(9) . . ? 
O3 C3 C2 120.09(8) . . ? 
C4 C3 C2 118.21(8) . . ? 
C9 C4 C5 118.58(9) . . ? 
C9 C4 C3 123.21(9) . . ? 
C5 C4 C3 118.21(8) . . ? 
C6 C5 C4 120.93(9) . . ? 
C6 C5 H5 120.3(7) . . ? 
C4 C5 H5 118.7(7) . . ? 
C5 C6 C7 119.64(9) . . ? 
C5 C6 H6 120.7(8) . . ? 
C7 C6 H6 119.6(8) . . ? 
O4 C7 C8 122.61(9) . . ? 
O4 C7 C6 116.93(9) . . ? 
C8 C7 C6 120.46(9) . . ? 
C9 C8 C7 119.63(9) . . ? 
C9 C8 H8 120.4(8) . . ? 
C7 C8 H8 120.0(8) . . ? 
C8 C9 C4 120.77(9) . . ? 
C8 C9 H9 120.4(8) . . ? 
C4 C9 H9 118.8(8) . . ? 
  
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 
C2 O1 C1 O2 -0.78(16) . . . . ? 
C1 O1 C2 C3 179.89(9) . . . . ? 
O1 C2 C3 O3 -7.16(13) . . . . ? 
O1 C2 C3 C4 172.58(8) . . . . ? 
O3 C3 C4 C9 -177.27(9) . . . . ? 
C2 C3 C4 C9 3.00(14) . . . . ? 
O3 C3 C4 C5 2.21(14) . . . . ? 
C2 C3 C4 C5 -177.52(8) . . . . ? 
C9 C4 C5 C6 -0.73(14) . . . . ? 
C3 C4 C5 C6 179.77(9) . . . . ? 
C4 C5 C6 C7 0.15(15) . . . . ? 
C5 C6 C7 O4 -179.74(9) . . . . ? 
C5 C6 C7 C8 0.50(15) . . . . ? 
O4 C7 C8 C9 179.69(9) . . . . ? 
C6 C7 C8 C9 -0.56(15) . . . . ? 
C7 C8 C9 C4 -0.03(14) . . . . ? 
C5 C4 C9 C8 0.66(14) . . . . ? 
C3 C4 C9 C8 -179.87(9) . . . . ? 
  
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 H4O O3  0.830(17) 1.877(16) 2.6671(11) 158.5(16) 1_565 
  
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              30.50 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.467 
_refine_diff_density_min   -0.236 
_refine_diff_density_rms    0.059 
