# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_bd87

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 O4'
_symmetry_space_group_name_Hall  -P2ybc
_chemical_formula_sum            'C10 H6 O4'
_chemical_formula_weight         190.15

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                   6.1142(12)
_cell_length_b                   12.283(3)
_cell_length_c                   5.6061(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.70(3)
_cell_angle_gamma                90.00
_cell_volume                     401.09(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8956
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      37.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             196
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9901
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_process_details   'Bruker SHELXTL'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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 Kappa Apex2 CCD'
_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_%        ?
_diffrn_reflns_number            8689
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         37.44
_reflns_number_total             2073
_reflns_number_gt                1791
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'Bruker Apex2'
_computing_data_reduction        'Bruker Apex2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0743P)²+0.0226P] 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         2073
_refine_ls_number_parameters     76
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.35901(8) 0.62813(4) -0.00069(8) 0.01743(11) Uani 1 1 d . . .
O2 O 0.20684(9) 0.34776(4) 0.46220(10) 0.02376(12) Uani 1 1 d . . .
C1 C 0.41964(9) 0.52258(4) 0.05706(10) 0.01376(11) Uani 1 1 d . . .
C2 C 0.30784(9) 0.48254(4) 0.21825(10) 0.01421(11) Uani 1 1 d . . .
C3 C 0.17079(10) 0.57063(5) 0.26261(11) 0.01671(11) Uani 1 1 d . . .
H3 H 0.069(2) 0.5669(9) 0.366(2) 0.027(3) Uiso 1 1 d . . .
C4 C 0.20683(10) 0.65572(5) 0.12668(11) 0.01824(12) Uani 1 1 d . . .
H4 H 0.1424(19) 0.7259(9) 0.095(2) 0.029(3) Uiso 1 1 d . . .
C5 C 0.31505(10) 0.37286(5) 0.31991(11) 0.01746(12) Uani 1 1 d . . .
H5 H 0.4076(18) 0.3173(10) 0.273(2) 0.028(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 0.0217(2) 0.01409(19) 0.0203(2) 0.00199(13) 0.01198(15) 0.00365(14)
O2 0.0278(2) 0.0216(2) 0.0284(2) 0.00355(17) 0.01827(19) -0.00153(17)
C1 0.0155(2) 0.0126(2) 0.0148(2) -0.00036(15) 0.00698(16) 0.00060(15)
C2 0.0152(2) 0.0138(2) 0.0154(2) -0.00099(15) 0.00732(16) -0.00065(15)
C3 0.0172(2) 0.0170(2) 0.0186(2) -0.00175(17) 0.00939(18) 0.00065(17)
C4 0.0205(2) 0.0165(2) 0.0209(2) -0.00033(18) 0.01093(19) 0.00361(18)
C5 0.0201(2) 0.0151(2) 0.0200(2) 0.00003(17) 0.01037(19) -0.00159(17)

_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 1.3602(7) . ?
O1 C4 1.3765(8) . ?
O2 C5 1.2208(8) . ?
C1 C2 1.3789(8) . ?
C1 C1 1.4370(11) 3_665 ?
C2 C3 1.4358(8) . ?
C2 C5 1.4582(9) . ?
C3 C4 1.3505(9) . ?
C3 H3 0.971(12) . ?
C4 H4 0.942(11) . ?
C5 H5 0.973(12) . ?

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 C4 106.83(4) . . ?
O1 C1 C2 110.02(5) . . ?
O1 C1 C1 115.83(6) . 3_665 ?
C2 C1 C1 134.15(7) . 3_665 ?
C1 C2 C3 106.05(5) . . ?
C1 C2 C5 128.57(5) . . ?
C3 C2 C5 125.34(5) . . ?
C4 C3 C2 106.35(5) . . ?
C4 C3 H3 128.1(7) . . ?
C2 C3 H3 125.5(7) . . ?
C3 C4 O1 110.74(5) . . ?
C3 C4 H4 133.1(7) . . ?
O1 C4 H4 116.0(7) . . ?
O2 C5 C2 122.06(6) . . ?
O2 C5 H5 118.4(7) . . ?
C2 C5 H5 119.5(7) . . ?

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
C4 O1 C1 C2 0.22(6) . . . . ?
C4 O1 C1 C1 -179.71(6) . . . 3_665 ?
O1 C1 C2 C3 -0.43(6) . . . . ?
C1 C1 C2 C3 179.49(8) 3_665 . . . ?
O1 C1 C2 C5 177.40(5) . . . . ?
C1 C1 C2 C5 -2.69(12) 3_665 . . . ?
C1 C2 C3 C4 0.47(6) . . . . ?
C5 C2 C3 C4 -177.44(5) . . . . ?
C2 C3 C4 O1 -0.36(7) . . . . ?
C1 O1 C4 C3 0.10(7) . . . . ?
C1 C2 C5 O2 -179.98(6) . . . . ?
C3 C2 C5 O2 -2.54(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        37.44
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 970220'
