# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_pf16

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Cl3 O2 S4 Zn'
_chemical_formula_weight         499.18

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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                   8.1418(8)
_cell_length_b                   8.9239(9)
_cell_length_c                   13.7644(13)
_cell_angle_alpha                73.404(3)
_cell_angle_beta                 79.141(3)
_cell_angle_gamma                75.735(3)
_cell_volume                     921.33(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4333
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      28.37

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    2.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5718
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10488
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         28.32
_reflns_number_total             4491
_reflns_number_gt                3850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0610P)²+0.7467P] 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       ?
_refine_ls_number_reflns         4491
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_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
Zn1 Zn 0.28641(4) -0.04061(4) 0.27744(3) 0.01716(12) Uani 1 1 d . . .
Cl1 Cl 0.81382(12) 0.46881(11) 0.72183(10) 0.0480(3) Uani 1 1 d . . .
Cl2 Cl 1.14659(12) 0.54394(13) 0.65690(8) 0.0450(3) Uani 1 1 d . . .
Cl3 Cl 0.96776(19) 0.57350(16) 0.85571(10) 0.0685(4) Uani 1 1 d . . .
S1 S 0.43172(10) -0.26554(9) 0.38045(6) 0.01837(17) Uani 1 1 d . . .
S2 S 0.30952(10) -0.04712(10) 0.67575(6) 0.02083(18) Uani 1 1 d . . .
S3 S 0.12092(10) -0.01975(10) 0.15523(6) 0.02291(19) Uani 1 1 d . . .
S4 S 0.45317(11) 0.29468(9) -0.11908(6) 0.02238(18) Uani 1 1 d . . .
O1 O 0.2019(3) 0.0488(2) 0.39616(16) 0.0176(4) Uani 1 1 d . . .
O2 O 0.4138(3) 0.1110(2) 0.17631(16) 0.0187(4) Uani 1 1 d . . .
C1 C 0.2711(4) -0.0313(3) 0.4793(2) 0.0151(6) Uani 1 1 d . . .
C2 C 0.3877(4) -0.1828(3) 0.4844(2) 0.0138(5) Uani 1 1 d . . .
C3 C 0.4703(4) -0.2661(4) 0.5714(2) 0.0183(6) Uani 1 1 d . . .
H3 H 0.5481 -0.3641 0.5690 0.022 Uiso 1 1 calc R . .
C4 C 0.4460(4) -0.2155(4) 0.6593(2) 0.0217(6) Uani 1 1 d . . .
H4 H 0.5094 -0.2788 0.7135 0.026 Uiso 1 1 calc R . .
C5 C 0.2266(4) 0.0347(4) 0.5645(2) 0.0181(6) Uani 1 1 d . . .
C6 C 0.1022(4) 0.1914(4) 0.5592(3) 0.0236(7) Uani 1 1 d . . .
H6A H 0.1513 0.2766 0.5090 0.035 Uiso 1 1 calc R . .
H6B H 0.0785 0.2146 0.6265 0.035 Uiso 1 1 calc R . .
H6C H -0.0044 0.1852 0.5387 0.035 Uiso 1 1 calc R . .
C7 C 0.3798(4) 0.1466(3) 0.0828(2) 0.0155(6) Uani 1 1 d . . .
C8 C 0.2401(4) 0.0940(3) 0.0592(2) 0.0164(6) Uani 1 1 d . . .
C9 C 0.2012(4) 0.1322(4) -0.0418(2) 0.0201(6) Uani 1 1 d . . .
H9 H 0.1084 0.0945 -0.0527 0.024 Uiso 1 1 calc R . .
C10 C 0.2867(4) 0.2190(4) -0.1247(2) 0.0230(7) Uani 1 1 d . . .
H10 H 0.2502 0.2379 -0.1895 0.028 Uiso 1 1 calc R . .
C11 C 0.4801(4) 0.2379(4) 0.0063(2) 0.0183(6) Uani 1 1 d . . .
C12 C 0.6248(4) 0.2900(4) 0.0320(3) 0.0263(7) Uani 1 1 d . . .
H12A H 0.5802 0.3573 0.0801 0.039 Uiso 1 1 calc R . .
H12B H 0.6821 0.3510 -0.0305 0.039 Uiso 1 1 calc R . .
H12C H 0.7067 0.1958 0.0632 0.039 Uiso 1 1 calc R . .
C13 C 0.9467(5) 0.5939(4) 0.7279(3) 0.0336(8) Uani 1 1 d . . .
H13 H 0.8934 0.7073 0.6972 0.040 Uiso 1 1 calc R . .

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
Zn1 0.0204(2) 0.01839(19) 0.01478(19) -0.00463(14) -0.00361(14) -0.00626(14)
Cl1 0.0239(5) 0.0265(5) 0.0882(9) -0.0069(5) 0.0013(5) -0.0104(4)
Cl2 0.0265(5) 0.0544(6) 0.0453(6) 0.0092(5) -0.0032(4) -0.0186(4)
Cl3 0.0823(10) 0.0570(8) 0.0595(8) -0.0343(6) -0.0219(7) 0.0308(7)
S1 0.0241(4) 0.0154(3) 0.0174(4) -0.0067(3) -0.0037(3) -0.0035(3)
S2 0.0228(4) 0.0274(4) 0.0166(4) -0.0094(3) -0.0014(3) -0.0095(3)
S3 0.0219(4) 0.0313(4) 0.0193(4) -0.0033(3) -0.0058(3) -0.0136(3)
S4 0.0292(4) 0.0222(4) 0.0158(4) -0.0039(3) -0.0012(3) -0.0077(3)
O1 0.0205(11) 0.0157(10) 0.0167(10) -0.0038(8) -0.0048(8) -0.0025(8)
O2 0.0236(11) 0.0216(11) 0.0149(10) -0.0041(8) -0.0057(8) -0.0104(9)
C1 0.0154(13) 0.0170(14) 0.0154(14) -0.0055(11) 0.0005(11) -0.0082(11)
C2 0.0147(13) 0.0149(13) 0.0141(13) -0.0035(11) -0.0010(11) -0.0080(11)
C3 0.0193(15) 0.0185(14) 0.0189(15) -0.0032(12) -0.0031(12) -0.0085(12)
C4 0.0233(16) 0.0240(16) 0.0190(15) -0.0009(12) -0.0056(12) -0.0103(13)
C5 0.0176(14) 0.0210(15) 0.0188(15) -0.0066(12) 0.0003(11) -0.0097(12)
C6 0.0240(16) 0.0232(16) 0.0249(17) -0.0122(13) 0.0000(13) -0.0022(13)
C7 0.0173(14) 0.0151(13) 0.0155(14) -0.0070(11) -0.0024(11) -0.0022(11)
C8 0.0160(14) 0.0155(13) 0.0194(15) -0.0077(12) -0.0049(11) -0.0007(11)
C9 0.0194(15) 0.0214(15) 0.0226(16) -0.0081(13) -0.0079(12) -0.0029(12)
C10 0.0275(17) 0.0238(16) 0.0186(16) -0.0079(13) -0.0084(13) 0.0003(13)
C11 0.0230(15) 0.0162(14) 0.0170(15) -0.0065(12) -0.0025(12) -0.0037(12)
C12 0.0309(18) 0.0285(17) 0.0244(17) -0.0050(14) -0.0031(14) -0.0175(14)
C13 0.0318(19) 0.0199(16) 0.047(2) -0.0039(16) -0.0078(17) -0.0051(14)

_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
Zn1 O1 1.957(2) . ?
Zn1 O2 1.979(2) . ?
Zn1 S3 2.2871(8) . ?
Zn1 S1 2.2968(8) . ?
Cl1 C13 1.763(4) . ?
Cl2 C13 1.759(4) . ?
Cl3 C13 1.752(4) . ?
S1 C2 1.732(3) . ?
S2 C4 1.679(3) . ?
S2 C5 1.686(3) . ?
S3 C8 1.720(3) . ?
S4 C10 1.679(3) . ?
S4 C11 1.695(3) . ?
O1 C1 1.309(3) . ?
O2 C7 1.301(3) . ?
C1 C5 1.409(4) . ?
C1 C2 1.440(4) . ?
C2 C3 1.410(4) . ?
C3 C4 1.374(4) . ?
C5 C6 1.503(4) . ?
C7 C11 1.398(4) . ?
C7 C8 1.452(4) . ?
C8 C9 1.411(4) . ?
C9 C10 1.360(5) . ?
C11 C12 1.500(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
O1 Zn1 O2 106.80(9) . . ?
O1 Zn1 S3 123.38(6) . . ?
O2 Zn1 S3 88.79(6) . . ?
O1 Zn1 S1 89.48(6) . . ?
O2 Zn1 S1 119.95(7) . . ?
S3 Zn1 S1 129.30(3) . . ?
C2 S1 Zn1 93.12(10) . . ?
C4 S2 C5 105.01(15) . . ?
C8 S3 Zn1 94.13(10) . . ?
C10 S4 C11 104.70(16) . . ?
C1 O1 Zn1 115.30(18) . . ?
C7 O2 Zn1 115.82(17) . . ?
O1 C1 C5 117.9(3) . . ?
O1 C1 C2 121.4(3) . . ?
C5 C1 C2 120.7(3) . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 S1 118.4(2) . . ?
C1 C2 S1 119.6(2) . . ?
C4 C3 C2 124.6(3) . . ?
C3 C4 S2 123.2(3) . . ?
C1 C5 C6 120.4(3) . . ?
C1 C5 S2 124.4(2) . . ?
C6 C5 S2 115.1(2) . . ?
O2 C7 C11 118.1(2) . . ?
O2 C7 C8 120.7(3) . . ?
C11 C7 C8 121.2(3) . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 S3 118.9(2) . . ?
C7 C8 S3 119.8(2) . . ?
C10 C9 C8 124.8(3) . . ?
C9 C10 S4 123.8(2) . . ?
C7 C11 C12 120.5(3) . . ?
C7 C11 S4 124.2(2) . . ?
C12 C11 S4 115.3(2) . . ?
Cl3 C13 Cl2 111.2(2) . . ?
Cl3 C13 Cl1 109.8(2) . . ?
Cl2 C13 Cl1 109.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.367
_refine_diff_density_min         -1.135
_refine_diff_density_rms         0.174
_database_code_depnum_ccdc_archive 'CCDC 1000544'
