 
data_solve
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H9 Cl O7'
_chemical_formula_weight          324.66
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    C2/c
_symmetry_space_group_name_hall  '-C 2yc'
 
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'
 '-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                    16.0510(8)
_cell_length_b                    5.5590(8)
_cell_length_c                    30.980(9)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.99(2)
_cell_angle_gamma                 90.00
_cell_volume                      2743.7(9)
_cell_formula_units_Z             8
_cell_measurement_temperature     140(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.09
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.572
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1328
_exptl_absorpt_coefficient_mu     0.313
_exptl_absorpt_correction_type    none
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       140(2)
_diffrn_radiation_wavelength      0.71073
_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             1922
_diffrn_reflns_av_R_equivalents   0.0000
_diffrn_reflns_av_sigmaI/netI     0.0961
_diffrn_reflns_limit_h_min        -18
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        5
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        33
_diffrn_reflns_theta_min          2.73
_diffrn_reflns_theta_max          25.02
_reflns_number_total              1922
_reflns_number_gt                 1158
_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)+(0.1647P)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          1922
_refine_ls_number_parameters      202
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1208
_refine_ls_R_factor_gt            0.0859
_refine_ls_wR_factor_ref          0.2499
_refine_ls_wR_factor_gt           0.2277
_refine_ls_goodness_of_fit_ref    0.987
_refine_ls_restrained_S_all       0.987
_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
Cl1 Cl 0.89333(8) -0.1670(3) 0.23082(5) 0.0309(5) Uani 1 1 d . . .
O6 O 0.6542(4) 0.6771(9) 0.10473(18) 0.0618(15) Uani 1 1 d . . .
O4 O 0.4913(4) 0.5677(10) 0.1029(2) 0.0661(16) Uani 1 1 d . . .
O3 O 0.5529(3) -0.1244(9) 0.19030(19) 0.0589(15) Uani 1 1 d . . .
H1 H 0.5930 -0.2087 0.2019 0.088 Uiso 1 1 calc R . .
O5 O 0.4791(7) 0.3524(16) 0.0430(3) 0.150(5) Uani 1 1 d . . .
C5 C 0.5239(5) 0.2090(13) 0.1447(3) 0.0518(19) Uani 1 1 d . . .
H2 H 0.4660 0.1697 0.1429 0.062 Uiso 1 1 calc R . .
C14 C 0.4135(7) 0.7423(17) 0.0424(3) 0.082(3) Uani 1 1 d . . .
H3 H 0.4514 0.8739 0.0369 0.124 Uiso 1 1 calc R . .
H4 H 0.3752 0.7965 0.0627 0.124 Uiso 1 1 calc R . .
H5 H 0.3810 0.6934 0.0150 0.124 Uiso 1 1 calc R . .
O2 O 0.8139(4) 0.5557(10) 0.13455(19) 0.0667(17) Uani 1 1 d . . .
O1 O 0.7094(3) -0.2176(10) 0.21673(18) 0.0610(15) Uani 1 1 d . . .
C8 C 0.6962(4) 0.3219(13) 0.1483(2) 0.0453(17) Uani 1 1 d . . .
C4 C 0.5838(5) 0.0649(13) 0.1689(2) 0.0481(19) Uani 1 1 d . . .
C13 C 0.4632(6) 0.5352(15) 0.0614(3) 0.063(2) Uani 1 1 d . . .
C10 C 0.8469(5) 0.2143(13) 0.1772(3) 0.052(2) Uani 1 1 d . . .
H6 H 0.9054 0.2455 0.1789 0.063 Uiso 1 1 calc R . .
C3 C 0.6690(4) 0.1157(13) 0.1712(2) 0.0440(18) Uani 1 1 d . . .
C1 C 0.8195(5) 0.0247(14) 0.1978(2) 0.0492(19) Uani 1 1 d . . .
C2 C 0.7311(5) -0.0366(14) 0.1969(2) 0.0482(18) Uani 1 1 d . . .
C6 C 0.5494(5) 0.4073(13) 0.1235(2) 0.0494(19) Uani 1 1 d . . .
C9 C 0.7870(5) 0.3745(14) 0.1521(2) 0.0530(19) Uani 1 1 d . . .
C7 C 0.6359(5) 0.4646(13) 0.1256(2) 0.0482(19) Uani 1 1 d . . .
O7 O 0.7041(4) 0.4789(10) 0.05037(18) 0.0687(17) Uani 1 1 d . . .
C11 C 0.6902(5) 0.6580(16) 0.0667(2) 0.056(2) Uani 1 1 d . . .
C12 C 0.7112(9) 0.9077(18) 0.0528(4) 0.115(5) Uani 1 1 d . . .
H7 H 0.7597 0.9683 0.0720 0.173 Uiso 1 1 calc R . .
H8 H 0.6630 1.0138 0.0546 0.173 Uiso 1 1 calc R . .
H9 H 0.7246 0.9038 0.0228 0.173 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
Cl1 C1 1.814(8) . ?
O6 C11 1.378(10) . ?
O6 C7 1.395(9) . ?
O4 C13 1.322(10) . ?
O4 C6 1.388(9) . ?
O3 C4 1.368(9) . ?
O3 H1 0.8400 . ?
O5 C13 1.207(10) . ?
C5 C6 1.370(11) . ?
C5 C4 1.397(11) . ?
C5 H2 0.9500 . ?
C14 C13 1.481(12) . ?
C14 H3 0.9800 . ?
C14 H4 0.9800 . ?
C14 H5 0.9800 . ?
O2 C9 1.246(9) . ?
O1 C2 1.250(9) . ?
C8 C7 1.377(10) . ?
C8 C3 1.443(10) . ?
C8 C9 1.477(11) . ?
C4 C3 1.390(10) . ?
C10 C1 1.333(10) . ?
C10 C9 1.464(11) . ?
C10 H6 0.9500 . ?
C3 C2 1.467(10) . ?
C1 C2 1.457(10) . ?
C6 C7 1.418(11) . ?
O7 C11 1.151(9) . ?
C11 C12 1.503(13) . ?
C12 H7 0.9800 . ?
C12 H8 0.9800 . ?
C12 H9 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
C11 O6 C7 117.7(6) . . ?
C13 O4 C6 119.4(6) . . ?
C4 O3 H1 109.5 . . ?
C6 C5 C4 119.5(7) . . ?
C6 C5 H2 120.2 . . ?
C4 C5 H2 120.2 . . ?
C13 C14 H3 109.5 . . ?
C13 C14 H4 109.5 . . ?
H3 C14 H4 109.5 . . ?
C13 C14 H5 109.5 . . ?
H3 C14 H5 109.5 . . ?
H4 C14 H5 109.5 . . ?
C7 C8 C3 118.2(7) . . ?
C7 C8 C9 123.5(7) . . ?
C3 C8 C9 118.2(7) . . ?
O3 C4 C3 122.9(7) . . ?
O3 C4 C5 115.8(7) . . ?
C3 C4 C5 121.2(7) . . ?
O5 C13 O4 120.4(8) . . ?
O5 C13 C14 127.0(8) . . ?
O4 C13 C14 112.6(7) . . ?
C1 C10 C9 120.1(7) . . ?
C1 C10 H6 120.0 . . ?
C9 C10 H6 120.0 . . ?
C4 C3 C8 119.4(7) . . ?
C4 C3 C2 120.6(7) . . ?
C8 C3 C2 119.9(6) . . ?
C10 C1 C2 123.6(7) . . ?
C10 C1 Cl1 120.2(6) . . ?
C2 C1 Cl1 116.2(6) . . ?
O1 C2 C1 120.6(7) . . ?
O1 C2 C3 121.3(7) . . ?
C1 C2 C3 118.1(7) . . ?
C5 C6 O4 120.9(7) . . ?
C5 C6 C7 120.4(7) . . ?
O4 C6 C7 118.4(7) . . ?
O2 C9 C10 119.0(7) . . ?
O2 C9 C8 121.1(7) . . ?
C10 C9 C8 120.0(7) . . ?
C8 C7 O6 123.3(7) . . ?
C8 C7 C6 121.2(7) . . ?
O6 C7 C6 115.5(7) . . ?
O7 C11 O6 124.5(8) . . ?
O7 C11 C12 127.7(8) . . ?
O6 C11 C12 107.8(8) . . ?
C11 C12 H7 109.5 . . ?
C11 C12 H8 109.5 . . ?
H7 C12 H8 109.5 . . ?
C11 C12 H9 109.5 . . ?
H7 C12 H9 109.5 . . ?
H8 C12 H9 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.794
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.794
_refine_diff_density_max    1.302
_refine_diff_density_min   -0.387
_refine_diff_density_rms    0.117
