# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
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data_r131217f1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl2 O4'
_chemical_formula_weight         339.16

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7369(15)
_cell_length_b                   7.9449(16)
_cell_length_c                   12.788(3)
_cell_angle_alpha                104.35(3)
_cell_angle_beta                 97.85(3)
_cell_angle_gamma                92.83(3)
_cell_volume                     751.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2241
_cell_measurement_theta_min      1.6635
_cell_measurement_theta_max      29.1664

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9160
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10081
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         29.20
_reflns_number_total             3946
_reflns_number_gt                2477
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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)+(0.0524P)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     SHELXL
_refine_ls_extinction_coef       0.043(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3946
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 -0.45583(6) 0.45292(7) -0.20333(4) 0.04867(18) Uani 1 1 d . . .
Cl2 Cl 0.15218(7) 1.16679(7) 0.69569(4) 0.04430(17) Uani 1 1 d . . .
O1 O 0.36164(16) 0.81860(19) -0.00702(11) 0.0471(4) Uani 1 1 d . . .
O2 O 0.22296(15) 0.92717(17) 0.13423(9) 0.0330(3) Uani 1 1 d . . .
O3 O 0.31129(16) 1.00195(15) 0.36396(10) 0.0336(3) Uani 1 1 d . . .
O4 O 0.2795(2) 1.22204(17) 0.50319(12) 0.0557(4) Uani 1 1 d . . .
C1 C 0.0520(2) 0.6094(2) -0.11834(14) 0.0332(4) Uani 1 1 d . . .
H1 H 0.1576 0.5825 -0.1466 0.040 Uiso 1 1 calc R . .
C2 C -0.1052(2) 0.5199(2) -0.17396(15) 0.0366(4) Uani 1 1 d . . .
H2 H -0.1083 0.4315 -0.2398 0.044 Uiso 1 1 calc R . .
C3 C -0.2574(2) 0.5616(2) -0.13179(15) 0.0314(4) Uani 1 1 d . . .
C4 C -0.2558(2) 0.6869(2) -0.03593(15) 0.0326(4) Uani 1 1 d . . .
H4 H -0.3616 0.7127 -0.0077 0.039 Uiso 1 1 calc R . .
C5 C -0.0978(2) 0.7752(2) 0.01907(14) 0.0303(4) Uani 1 1 d . . .
H5 H -0.0952 0.8621 0.0855 0.036 Uiso 1 1 calc R . .
C6 C 0.0572(2) 0.7377(2) -0.02217(13) 0.0266(4) Uani 1 1 d . . .
C7 C 0.2293(2) 0.8294(2) 0.03348(15) 0.0307(4) Uani 1 1 d . . .
C8 C 0.3873(2) 1.0202(2) 0.19376(14) 0.0328(4) Uani 1 1 d . . .
H8A H 0.4341 1.0982 0.1528 0.039 Uiso 1 1 calc R . .
H8B H 0.4748 0.9369 0.2047 0.039 Uiso 1 1 calc R . .
C9 C 0.3497(2) 1.1241(2) 0.30124(15) 0.0324(4) Uani 1 1 d . . .
H9A H 0.4523 1.2058 0.3400 0.039 Uiso 1 1 calc R . .
H9B H 0.2483 1.1925 0.2904 0.039 Uiso 1 1 calc R . .
C10 C 0.2786(2) 1.0694(2) 0.46487(14) 0.0287(4) Uani 1 1 d . . .
C11 C 0.2441(2) 0.9289(2) 0.52065(14) 0.0263(4) Uani 1 1 d . . .
C12 C 0.2710(2) 0.7576(2) 0.46958(15) 0.0327(4) Uani 1 1 d . . .
H12 H 0.3129 0.7336 0.4014 0.039 Uiso 1 1 calc R . .
C13 C 0.2380(3) 0.6225(2) 0.51609(17) 0.0416(5) Uani 1 1 d . . .
H13 H 0.2566 0.5066 0.4800 0.050 Uiso 1 1 calc R . .
C14 C 0.1778(3) 0.6565(3) 0.61518(17) 0.0452(5) Uani 1 1 d . . .
H14 H 0.1531 0.5634 0.6468 0.054 Uiso 1 1 calc R . .
C15 C 0.1534(2) 0.8237(3) 0.66847(16) 0.0406(5) Uani 1 1 d . . .
H15 H 0.1143 0.8465 0.7375 0.049 Uiso 1 1 calc R . .
C16 C 0.1857(2) 0.9600(2) 0.62160(14) 0.0307(4) Uani 1 1 d . . .


_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
Cl1 C3 1.7417(19) . ?
Cl2 C16 1.7328(19) . ?
O1 C7 1.207(2) . ?
O2 C7 1.338(2) . ?
O2 C8 1.451(2) . ?
O3 C10 1.333(2) . ?
O3 C9 1.448(2) . ?
O4 C10 1.190(2) . ?
C1 C6 1.384(3) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(3) . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.483(2) . ?
C8 C9 1.492(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.497(2) . ?
C11 C16 1.394(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 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
C7 O2 C8 115.79(13) . . ?
C10 O3 C9 116.81(13) . . ?
C6 C1 C2 120.78(17) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 118.72(17) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 121.70(17) . . ?
C4 C3 Cl1 119.50(14) . . ?
C2 C3 Cl1 118.79(15) . . ?
C3 C4 C5 119.02(16) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 120.55(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.22(16) . . ?
C1 C6 C7 118.30(16) . . ?
C5 C6 C7 122.48(16) . . ?
O1 C7 O2 123.01(17) . . ?
O1 C7 C6 124.17(17) . . ?
O2 C7 C6 112.82(15) . . ?
O2 C8 C9 106.89(14) . . ?
O2 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
O3 C9 C8 107.25(14) . . ?
O3 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
O4 C10 O3 122.76(16) . . ?
O4 C10 C11 126.18(17) . . ?
O3 C10 C11 111.06(14) . . ?
C16 C11 C12 117.82(16) . . ?
C16 C11 C10 123.36(16) . . ?
C12 C11 C10 118.82(16) . . ?
C13 C12 C11 121.33(18) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.64(19) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.47(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.02(19) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.70(17) . . ?
C15 C16 Cl2 116.54(15) . . ?
C11 C16 Cl2 122.75(14) . . ?

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
C6 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 Cl1 178.44(14) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
Cl1 C3 C4 C5 -178.61(13) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C7 -179.83(16) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.67(16) . . . . ?
C8 O2 C7 O1 -0.5(3) . . . . ?
C8 O2 C7 C6 179.76(14) . . . . ?
C1 C6 C7 O1 11.5(3) . . . . ?
C5 C6 C7 O1 -168.94(18) . . . . ?
C1 C6 C7 O2 -168.81(15) . . . . ?
C5 C6 C7 O2 10.8(2) . . . . ?
C7 O2 C8 C9 178.25(14) . . . . ?
C10 O3 C9 C8 178.17(14) . . . . ?
O2 C8 C9 O3 69.70(17) . . . . ?
C9 O3 C10 O4 0.3(3) . . . . ?
C9 O3 C10 C11 -179.06(14) . . . . ?
O4 C10 C11 C16 8.7(3) . . . . ?
O3 C10 C11 C16 -172.04(15) . . . . ?
O4 C10 C11 C12 -171.48(19) . . . . ?
O3 C10 C11 C12 7.8(2) . . . . ?
C16 C11 C12 C13 1.2(3) . . . . ?
C10 C11 C12 C13 -178.67(16) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C14 C15 C16 Cl2 -179.65(15) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C10 C11 C16 C15 178.96(16) . . . . ?
C12 C11 C16 Cl2 178.35(13) . . . . ?
C10 C11 C16 Cl2 -1.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        29.20
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 1009912'
