 
data_resolve
 
_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            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
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                    11.336(9)
_cell_length_b                    12.996(3)
_cell_length_c                    11.379(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  108.85(4)
_cell_angle_gamma                 90.00
_cell_volume                      1586.5(13)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.35
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.391
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              704
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type    none
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source     	  'rotating anode generator'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type     'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number           'None'
_diffrn_standards_interval_count   'N/A'
_diffrn_standards_interval_time    'N/A'
_diffrn_standards_decay_%          'N/A'
_diffrn_reflns_number             2394
_diffrn_reflns_av_R_equivalents   0.4766
_diffrn_reflns_av_sigmaI/netI     0.1212
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        -2
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        0
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.98
_diffrn_reflns_theta_max          27.15
_reflns_number_total              2136
_reflns_number_gt                 1245
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0469P)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        0
_refine_ls_number_reflns          2136
_refine_ls_number_parameters      221
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0938
_refine_ls_R_factor_gt            0.0456
_refine_ls_wR_factor_ref          0.1073
_refine_ls_wR_factor_gt           0.0933
_refine_ls_goodness_of_fit_ref    0.898
_refine_ls_restrained_S_all       0.898
_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
O6 O 0.69462(13) -0.02933(13) 0.53905(14) 0.0251(4) Uani 1 1 d . . .
O2 O 0.89742(14) -0.02091(14) 0.83378(16) 0.0347(5) Uani 1 1 d . . .
O3 O 0.80446(13) 0.03753(13) 0.96134(14) 0.0267(4) Uani 1 1 d . . .
O5 O 0.59885(13) -0.09000(14) 0.66361(14) 0.0301(4) Uani 1 1 d . . .
O4 O 0.55947(16) 0.39180(14) 0.71223(17) 0.0370(5) Uani 1 1 d . . .
H4 H 0.5173 0.3970 0.7606 0.055 Uiso 1 1 calc R . .
O1 O 0.97936(16) 0.45842(15) 0.82581(17) 0.0398(5) Uani 1 1 d . . .
H1 H 1.0152 0.4640 0.7721 0.060 Uiso 1 1 calc R . .
C15 C 0.6278(2) 0.2684(2) 0.6027(2) 0.0284(6) Uani 1 1 d . . .
H15 H 0.6509 0.3219 0.5575 0.034 Uiso 1 1 calc R . .
C13 C 0.61403(18) 0.08962(19) 0.6419(2) 0.0221(6) Uani 1 1 d . . .
C7 C 0.8676(2) 0.0512(2) 0.8844(2) 0.0246(6) Uani 1 1 d . . .
C14 C 0.64653(19) 0.16927(19) 0.5782(2) 0.0250(6) Uani 1 1 d . . .
H14 H 0.6828 0.1540 0.5157 0.030 Uiso 1 1 calc R . .
C4 C 0.89465(18) 0.15788(19) 0.8687(2) 0.0223(6) Uani 1 1 d . . .
C17 C 0.7172(2) -0.13362(19) 0.5103(2) 0.0284(6) Uani 1 1 d . . .
H17A H 0.6383 -0.1733 0.4844 0.034 Uiso 1 1 calc R . .
H17B H 0.7762 -0.1675 0.5838 0.034 Uiso 1 1 calc R . .
C6 C 0.8946(2) 0.3357(2) 0.9215(2) 0.0318(6) Uani 1 1 d . . .
H6 H 0.8745 0.3884 0.9697 0.038 Uiso 1 1 calc R . .
C2 C 0.97900(19) 0.2834(2) 0.7669(2) 0.0273(6) Uani 1 1 d . . .
H2 H 1.0177 0.3002 0.7068 0.033 Uiso 1 1 calc R . .
C11 C 0.5429(2) 0.2148(2) 0.7564(2) 0.0255(6) Uani 1 1 d . . .
H11 H 0.5061 0.2308 0.8183 0.031 Uiso 1 1 calc R . .
C18 C 0.7704(2) -0.1282(2) 0.4082(2) 0.0367(7) Uani 1 1 d . . .
H18A H 0.7130 -0.0911 0.3379 0.055 Uiso 1 1 calc R . .
H18B H 0.7833 -0.1980 0.3821 0.055 Uiso 1 1 calc R . .
H18C H 0.8505 -0.0919 0.4367 0.055 Uiso 1 1 calc R . .
C8 C 0.7743(2) -0.0670(2) 0.9803(2) 0.0293(6) Uani 1 1 d . . .
H8A H 0.8513 -0.1081 1.0148 0.035 Uiso 1 1 calc R . .
H8B H 0.7236 -0.0983 0.9007 0.035 Uiso 1 1 calc R . .
C10 C 0.5760(2) 0.2922(2) 0.6917(2) 0.0243(6) Uani 1 1 d . . .
C1 C 0.9513(2) 0.3594(2) 0.8364(2) 0.0285(6) Uani 1 1 d . . .
C3 C 0.95157(19) 0.1843(2) 0.7834(2) 0.0267(6) Uani 1 1 d . . .
H3 H 0.9721 0.1320 0.7350 0.032 Uiso 1 1 calc R . .
C9 C 0.7035(3) -0.0645(2) 1.0681(3) 0.0456(8) Uani 1 1 d . . .
H9A H 0.7537 -0.0311 1.1453 0.068 Uiso 1 1 calc R . .
H9B H 0.6835 -0.1349 1.0860 0.068 Uiso 1 1 calc R . .
H9C H 0.6261 -0.0257 1.0315 0.068 Uiso 1 1 calc R . .
C12 C 0.56252(18) 0.11468(19) 0.73218(19) 0.0244(6) Uani 1 1 d . . .
H12 H 0.5403 0.0615 0.7783 0.029 Uiso 1 1 calc R . .
C16 C 0.6339(2) -0.0168(2) 0.6180(2) 0.0238(6) Uani 1 1 d . . .
C5 C 0.86699(19) 0.2363(2) 0.9370(2) 0.0269(6) Uani 1 1 d . . .
H5 H 0.8274 0.2202 0.9967 0.032 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O6 C16 1.306(3) . ?
O6 C17 1.436(3) . ?
O2 C7 1.204(3) . ?
O3 C7 1.310(3) . ?
O3 C8 1.434(3) . ?
O5 C16 1.211(3) . ?
O4 C10 1.340(3) . ?
O4 H4 0.8400 . ?
O1 C1 1.340(3) . ?
O1 H1 0.8400 . ?
C15 C14 1.349(3) . ?
C15 C10 1.360(3) . ?
C15 H15 0.9500 . ?
C13 C12 1.374(3) . ?
C13 C14 1.381(3) . ?
C13 C16 1.442(3) . ?
C7 C4 1.444(4) . ?
C14 H14 0.9500 . ?
C4 C3 1.371(3) . ?
C4 C5 1.378(3) . ?
C17 C18 1.475(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C6 C5 1.354(4) . ?
C6 C1 1.360(3) . ?
C6 H6 0.9500 . ?
C2 C3 1.353(4) . ?
C2 C1 1.364(4) . ?
C2 H2 0.9500 . ?
C11 C12 1.363(3) . ?
C11 C10 1.369(3) . ?
C11 H11 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C8 C9 1.470(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C3 H3 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 H12 0.9500 . ?
C5 H5 0.9500 . ?
 
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
C16 O6 C17 116.48(19) . . ?
C7 O3 C8 115.9(2) . . ?
C10 O4 H4 109.5 . . ?
C1 O1 H1 109.5 . . ?
C14 C15 C10 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C12 C13 C14 117.7(2) . . ?
C12 C13 C16 119.9(2) . . ?
C14 C13 C16 122.4(2) . . ?
O2 C7 O3 120.9(2) . . ?
O2 C7 C4 125.8(2) . . ?
O3 C7 C4 113.4(2) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C3 C4 C5 117.3(2) . . ?
C3 C4 C7 119.7(2) . . ?
C5 C4 C7 123.0(2) . . ?
O6 C17 C18 106.4(2) . . ?
O6 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O6 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C8 C9 106.8(2) . . ?
O3 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O3 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
O4 C10 C15 117.9(2) . . ?
O4 C10 C11 122.6(2) . . ?
C15 C10 C11 119.5(2) . . ?
O1 C1 C6 117.5(2) . . ?
O1 C1 C2 122.5(2) . . ?
C6 C1 C2 120.0(3) . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
O5 C16 O6 121.1(2) . . ?
O5 C16 C13 125.4(2) . . ?
O6 C16 C13 113.5(2) . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
 
_diffrn_measured_fraction_theta_max    0.607
_diffrn_reflns_theta_full              27.15
_diffrn_measured_fraction_theta_full   0.607
_refine_diff_density_max    0.206
_refine_diff_density_min   -0.207
_refine_diff_density_rms    0.053
