# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_197cut_a
_database_code_depnum_ccdc_archive 'CCDC 1438353'
_audit_update_record             
;
2015-11-23 deposited with the CCDC.
2016-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H5 Cl2 O3 Tl'
_chemical_formula_weight         424.39

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'
Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.903(2)
_cell_length_b                   3.9651(5)
_cell_length_c                   13.9329(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.904(4)
_cell_angle_gamma                90
_cell_volume                     977.1(2)
_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       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.885
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    17.049
_shelx_estimated_absorpt_T_min   0.043
_shelx_estimated_absorpt_T_max   0.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2283
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71120   13.885    3.951   17.844   89.865   98.729   90.259
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3238
_diffrn_reflns_av_unetI/netI     0.0873
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.888
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.888
_reflns_number_total             1748
_reflns_number_gt                1362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       BrukerAPEX2
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1091P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1748
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tl1 Tl 0.05469(3) 0.84810(14) 0.13750(4) 0.0328(3) Uani 1 1 d . . . . .
C1 C 0.0953(9) 0.942(3) 0.4034(10) 0.027(3) Uani 1 1 d . . . . .
C2 C 0.1751(8) 0.808(4) 0.4213(9) 0.023(3) Uani 1 1 d . . . . .
H2A H 0.2097 0.9932 0.4402 0.028 Uiso 1 1 calc R U . . .
H2B H 0.1801 0.6489 0.4749 0.028 Uiso 1 1 calc R U . . .
C3 C 0.2689(7) 0.525(3) 0.3485(10) 0.024(3) Uani 1 1 d . . . . .
C4 C 0.2904(9) 0.379(3) 0.2665(10) 0.028(3) Uani 1 1 d . . . . .
C5 C 0.3624(9) 0.247(4) 0.2693(11) 0.031(4) Uani 1 1 d . . . . .
H5 H 0.3772 0.1508 0.2144 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4110(9) 0.263(4) 0.3553(11) 0.032(3) Uani 1 1 d . . . . .
C7 C 0.3901(10) 0.401(3) 0.4374(11) 0.033(3) Uani 1 1 d . . . . .
H7 H 0.4236 0.4045 0.4955 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3201(9) 0.534(4) 0.4323(11) 0.033(3) Uani 1 1 d . . . . .
H8 H 0.3062 0.6331 0.4874 0.040 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2272(3) 0.3596(10) 0.1583(3) 0.0414(10) Uani 1 1 d . . . . .
Cl2 Cl 0.5025(2) 0.0991(11) 0.3604(3) 0.0465(11) Uani 1 1 d . . . . .
O1 O 0.0821(6) 1.131(3) 0.4716(8) 0.038(3) Uani 1 1 d . . . . .
O2 O 0.0511(6) 0.861(3) 0.3311(7) 0.036(3) Uani 1 1 d . . . . .
O3 O 0.1958(6) 0.647(2) 0.3390(7) 0.031(2) 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
Tl1 O2 2.708(10) . ?
Tl1 O2 2.786(10) 2_545 ?
C1 O2 1.223(18) . ?
C1 O1 1.261(16) . ?
C1 C2 1.51(2) . ?
C2 O3 1.412(14) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.37(2) . ?
C3 O3 1.381(16) . ?
C3 C4 1.386(18) . ?
C4 C5 1.39(2) . ?
C4 Cl1 1.740(16) . ?
C5 C6 1.37(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.37(2) . ?
C6 Cl2 1.754(15) . ?
C7 C8 1.35(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
O2 Tl1 2.787(10) 2 ?

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
O2 Tl1 O2 74.7(3) . 2_545 ?
O2 C1 O1 127.1(15) . . ?
O2 C1 C2 121.3(12) . . ?
O1 C1 C2 111.6(13) . . ?
O3 C2 C1 112.7(12) . . ?
O3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
O3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C8 C3 O3 124.9(12) . . ?
C8 C3 C4 118.6(13) . . ?
O3 C3 C4 116.5(13) . . ?
C3 C4 C5 120.7(14) . . ?
C3 C4 Cl1 120.4(12) . . ?
C5 C4 Cl1 118.9(11) . . ?
C6 C5 C4 118.0(13) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C7 122.0(15) . . ?
C5 C6 Cl2 118.8(12) . . ?
C7 C6 Cl2 119.2(14) . . ?
C8 C7 C6 118.8(17) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C3 121.9(14) . . ?
C7 C8 H8 119.1 . . ?
C3 C8 H8 119.1 . . ?
C1 O2 Tl1 135.6(9) . . ?
C1 O2 Tl1 93.3(9) . 2 ?
Tl1 O2 Tl1 106.9(4) . 2 ?
C3 O3 C2 116.3(11) . . ?

_refine_diff_density_max         4.271
_refine_diff_density_min         -3.016
_refine_diff_density_rms         0.392



