# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_16sept
_database_code_depnum_ccdc_archive 'CCDC 878312'
_audit_update_record             
;
2012-04-24 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_FaizAhmedKhan_1335240264.16sept.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 Cl4 O2'
_chemical_formula_sum            'C11 H8 Cl4 O2'
_chemical_formula_weight         313.97

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   'P 21/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                   8.932(5)
_cell_length_b                   11.791(5)
_cell_length_c                   11.668(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.317(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1212.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8936
_exptl_absorpt_correction_T_max  0.9102
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        2
_diffrn_reflns_number            2272
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2129
_reflns_number_gt                1599
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  ?

_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)+(0.0435P)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       0.0106(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2129
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.65141(8) -0.21789(5) 0.71617(6) 0.0383(2) Uani 1 1 d . . .
Cl2 Cl 0.82758(8) -0.19537(6) 0.48950(6) 0.0382(2) Uani 1 1 d . . .
Cl3 Cl 0.47051(7) 0.02926(6) 0.70362(6) 0.0374(2) Uani 1 1 d . . .
Cl4 Cl 0.61661(9) 0.20934(6) 0.56526(6) 0.0439(2) Uani 1 1 d . . .
O5 O 0.9670(2) -0.09070(17) 0.88522(17) 0.0431(5) Uani 1 1 d . . .
O6 O 0.8476(2) 0.06825(16) 0.45695(15) 0.0380(5) Uani 1 1 d . . .
C7 C 0.7027(3) -0.0947(2) 0.6587(2) 0.0256(6) Uani 1 1 d . . .
C8 C 0.9152(3) -0.0066(2) 0.8356(2) 0.0299(6) Uani 1 1 d . . .
C9 C 0.7429(3) 0.1042(2) 0.6332(2) 0.0263(5) Uani 1 1 d . . .
C10 C 0.7563(3) 0.0421(2) 0.8368(2) 0.0267(5) Uani 1 1 d . . .
C11 C 0.7724(3) -0.0862(2) 0.5670(2) 0.0263(6) Uani 1 1 d . . .
C12 C 0.8684(3) 0.1598(2) 0.7210(2) 0.0331(6) Uani 1 1 d . . .
H12 H 0.9057 0.2319 0.6948 0.040 Uiso 1 1 calc R . .
C13 C 0.7901(3) 0.1697(2) 0.8271(2) 0.0330(6) Uani 1 1 d . . .
H13A H 0.6985 0.2152 0.8124 0.040 Uiso 1 1 calc R . .
H13B H 0.8571 0.1984 0.8946 0.040 Uiso 1 1 calc R . .
C14 C 0.7965(3) 0.0325(2) 0.5383(2) 0.0269(6) Uani 1 1 d . . .
C15 C 0.6831(3) 0.0019(3) 0.9369(2) 0.0405(7) Uani 1 1 d . . .
H15A H 0.5842 0.0353 0.9317 0.061 Uiso 1 1 calc R . .
H15B H 0.7445 0.0239 1.0087 0.061 Uiso 1 1 calc R . .
H15C H 0.6738 -0.0792 0.9341 0.061 Uiso 1 1 calc R . .
C16 C 0.9933(3) 0.0730(2) 0.7630(2) 0.0340(6) Uani 1 1 d . . .
H16A H 1.0258 0.0337 0.6983 0.041 Uiso 1 1 calc R . .
H16B H 1.0805 0.1090 0.8093 0.041 Uiso 1 1 calc R . .
C17 C 0.6711(3) 0.0173(2) 0.7107(2) 0.0246(5) Uani 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
Cl1 0.0500(4) 0.0249(4) 0.0410(4) 0.0063(3) 0.0102(3) -0.0059(3)
Cl2 0.0454(4) 0.0325(4) 0.0384(4) -0.0125(3) 0.0116(3) 0.0019(3)
Cl3 0.0264(3) 0.0417(4) 0.0451(4) 0.0006(3) 0.0084(3) 0.0029(3)
Cl4 0.0536(5) 0.0330(4) 0.0462(4) 0.0140(3) 0.0117(3) 0.0143(3)
O5 0.0405(11) 0.0434(13) 0.0442(12) 0.0046(9) 0.0030(9) 0.0071(9)
O6 0.0453(12) 0.0414(11) 0.0302(10) 0.0053(9) 0.0150(9) -0.0029(9)
C7 0.0271(13) 0.0215(13) 0.0271(13) 0.0007(10) 0.0013(11) -0.0025(10)
C8 0.0319(13) 0.0312(14) 0.0258(13) -0.0078(11) 0.0026(11) -0.0033(12)
C9 0.0305(14) 0.0212(12) 0.0277(13) 0.0037(10) 0.0061(11) 0.0022(11)
C10 0.0307(13) 0.0285(13) 0.0219(12) -0.0014(10) 0.0080(10) -0.0002(11)
C11 0.0272(13) 0.0245(14) 0.0266(13) -0.0046(10) 0.0031(11) 0.0018(10)
C12 0.0405(15) 0.0249(13) 0.0358(14) -0.0020(12) 0.0120(12) -0.0085(12)
C13 0.0405(15) 0.0285(14) 0.0311(14) -0.0082(11) 0.0090(12) -0.0032(12)
C14 0.0268(12) 0.0289(14) 0.0249(13) 0.0007(11) 0.0042(11) -0.0012(11)
C15 0.0467(16) 0.0489(18) 0.0285(15) -0.0017(13) 0.0142(13) -0.0019(14)
C16 0.0279(13) 0.0419(16) 0.0327(14) -0.0063(12) 0.0065(11) -0.0086(12)
C17 0.0239(12) 0.0251(13) 0.0254(13) -0.0001(10) 0.0060(10) 0.0002(10)

_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 C7 1.694(2) . ?
Cl2 C11 1.692(2) . ?
Cl3 C17 1.786(3) . ?
Cl4 C9 1.774(2) . ?
O5 C8 1.202(3) . ?
O6 C14 1.194(3) . ?
C7 C11 1.326(4) . ?
C7 C17 1.499(3) . ?
C8 C16 1.509(4) . ?
C8 C10 1.533(4) . ?
C9 C14 1.531(3) . ?
C9 C12 1.537(4) . ?
C9 C17 1.570(3) . ?
C10 C15 1.505(4) . ?
C10 C13 1.542(4) . ?
C10 C17 1.570(3) . ?
C11 C14 1.463(3) . ?
C12 C13 1.522(3) . ?
C12 C16 1.535(4) . ?

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 C7 C17 113.8(2) . . ?
C11 C7 Cl1 125.2(2) . . ?
C17 C7 Cl1 120.97(18) . . ?
O5 C8 C16 127.4(3) . . ?
O5 C8 C10 126.1(2) . . ?
C16 C8 C10 106.5(2) . . ?
C14 C9 C12 115.9(2) . . ?
C14 C9 C17 105.2(2) . . ?
C12 C9 C17 102.50(19) . . ?
C14 C9 Cl4 108.25(17) . . ?
C12 C9 Cl4 110.00(18) . . ?
C17 C9 Cl4 115.09(17) . . ?
C15 C10 C8 114.1(2) . . ?
C15 C10 C13 118.6(2) . . ?
C8 C10 C13 99.9(2) . . ?
C15 C10 C17 117.6(2) . . ?
C8 C10 C17 103.36(19) . . ?
C13 C10 C17 100.59(19) . . ?
C7 C11 C14 111.3(2) . . ?
C7 C11 Cl2 126.1(2) . . ?
C14 C11 Cl2 122.63(19) . . ?
C13 C12 C16 101.3(2) . . ?
C13 C12 C9 101.1(2) . . ?
C16 C12 C9 110.1(2) . . ?
C12 C13 C10 96.07(19) . . ?
O6 C14 C11 127.5(2) . . ?
O6 C14 C9 125.8(2) . . ?
C11 C14 C9 106.7(2) . . ?
C8 C16 C12 102.5(2) . . ?
C7 C17 C9 102.74(19) . . ?
C7 C17 C10 116.6(2) . . ?
C9 C17 C10 103.71(19) . . ?
C7 C17 Cl3 107.70(17) . . ?
C9 C17 Cl3 114.97(17) . . ?
C10 C17 Cl3 111.05(16) . . ?

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
O5 C8 C10 C15 20.1(4) . . . . ?
C16 C8 C10 C15 -158.4(2) . . . . ?
O5 C8 C10 C13 147.8(3) . . . . ?
C16 C8 C10 C13 -30.8(2) . . . . ?
O5 C8 C10 C17 -108.7(3) . . . . ?
C16 C8 C10 C17 72.7(2) . . . . ?
C17 C7 C11 C14 -1.6(3) . . . . ?
Cl1 C7 C11 C14 178.45(18) . . . . ?
C17 C7 C11 Cl2 178.73(18) . . . . ?
Cl1 C7 C11 Cl2 -1.2(4) . . . . ?
C14 C9 C12 C13 -152.9(2) . . . . ?
C17 C9 C12 C13 -39.0(2) . . . . ?
Cl4 C9 C12 C13 83.9(2) . . . . ?
C14 C9 C12 C16 -46.3(3) . . . . ?
C17 C9 C12 C16 67.6(2) . . . . ?
Cl4 C9 C12 C16 -169.54(17) . . . . ?
C16 C12 C13 C10 -55.4(2) . . . . ?
C9 C12 C13 C10 57.9(2) . . . . ?
C15 C10 C13 C12 176.7(2) . . . . ?
C8 C10 C13 C12 52.1(2) . . . . ?
C17 C10 C13 C12 -53.7(2) . . . . ?
C7 C11 C14 O6 -175.1(3) . . . . ?
Cl2 C11 C14 O6 4.5(4) . . . . ?
C7 C11 C14 C9 4.7(3) . . . . ?
Cl2 C11 C14 C9 -175.66(17) . . . . ?
C12 C9 C14 O6 -73.4(3) . . . . ?
C17 C9 C14 O6 174.2(2) . . . . ?
Cl4 C9 C14 O6 50.7(3) . . . . ?
C12 C9 C14 C11 106.8(2) . . . . ?
C17 C9 C14 C11 -5.6(2) . . . . ?
Cl4 C9 C14 C11 -129.11(18) . . . . ?
O5 C8 C16 C12 178.2(3) . . . . ?
C10 C8 C16 C12 -3.2(3) . . . . ?
C13 C12 C16 C8 36.8(2) . . . . ?
C9 C12 C16 C8 -69.6(2) . . . . ?
C11 C7 C17 C9 -2.0(3) . . . . ?
Cl1 C7 C17 C9 177.91(16) . . . . ?
C11 C7 C17 C10 -114.7(2) . . . . ?
Cl1 C7 C17 C10 65.3(3) . . . . ?
C11 C7 C17 Cl3 119.7(2) . . . . ?
Cl1 C7 C17 Cl3 -60.3(2) . . . . ?
C14 C9 C17 C7 4.6(2) . . . . ?
C12 C9 C17 C7 -117.0(2) . . . . ?
Cl4 C9 C17 C7 123.61(18) . . . . ?
C14 C9 C17 C10 126.5(2) . . . . ?
C12 C9 C17 C10 4.9(2) . . . . ?
Cl4 C9 C17 C10 -114.51(18) . . . . ?
C14 C9 C17 Cl3 -112.1(2) . . . . ?
C12 C9 C17 Cl3 126.30(19) . . . . ?
Cl4 C9 C17 Cl3 6.9(2) . . . . ?
C15 C10 C17 C7 -87.3(3) . . . . ?
C8 C10 C17 C7 39.3(3) . . . . ?
C13 C10 C17 C7 142.3(2) . . . . ?
C15 C10 C17 C9 160.6(2) . . . . ?
C8 C10 C17 C9 -72.8(2) . . . . ?
C13 C10 C17 C9 30.2(2) . . . . ?
C15 C10 C17 Cl3 36.5(3) . . . . ?
C8 C10 C17 Cl3 163.23(17) . . . . ?
C13 C10 C17 Cl3 -93.78(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.062


