# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_im41
_database_code_depnum_ccdc_archive 'CCDC 930737'
_audit_update_record             
;
2013-03-23 deposited with the CCDC.
2015-01-29 downloaded from the CCDC.
;
#TrackingRef '18798_web_deposit_cif_file_0_FarukhArjmand_1364027878.im41.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H17 Cl4 N3 O4 Sn'
_chemical_formula_weight         479.74

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'
N N 0.0061 0.0033 '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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Ima2

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

_cell_length_a                   13.9718(3)
_cell_length_b                   9.8400(2)
_cell_length_c                   11.9523(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1643.23(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4076
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.118
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    2.218
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.75246
_exptl_absorpt_correction_T_max  0.82193
_exptl_absorpt_process_details   'Alcock(1970) crystallographic computing,p271'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'CCD Saphire 3 Xcalibur'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1852
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6402
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1852
_reflns_number_gt                1782
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_cell_refinement       
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.35.11'
_computing_data_reduction        
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.35.11'

_computing_structure_solution    'SIR-97_(Altomare & al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY 2.4.5(CCDC, 2011)'
_computing_publication_material  'WINGX (Farrugia, 1999)'

_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)+(0.0179P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_number_reflns         1852
_refine_ls_number_parameters     97
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0388
_refine_ls_wR_factor_gt          0.0386
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_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
Sn1 Sn 0.7500 0.98610(2) 0.36423(3) 0.01892(7) Uani 1 2 d S . .
Cl1 Cl 0.62479(6) 1.12394(8) 0.43437(7) 0.0372(2) Uani 1 1 d . . .
Cl2 Cl 0.7500 0.81350(11) 0.50025(9) 0.0360(3) Uani 1 2 d S . .
Cl3 Cl 0.7500 0.41488(9) 0.27577(10) 0.0302(2) Uani 1 2 d S . .
O1 O 0.65011(13) 0.87614(17) 0.27079(17) 0.0250(5) Uani 1 1 d . . .
O2 O 0.56205(14) 0.8701(2) 0.11760(17) 0.0276(5) Uani 1 1 d . . .
N1 N 0.7500 1.0994(3) 0.2035(3) 0.0177(7) Uani 1 2 d S . .
H1 H 0.7500 1.1921 0.2185 0.021 Uiso 1 2 calc SR . .
N2 N 0.57207(16) 0.6019(2) 0.2568(2) 0.0260(6) Uani 1 1 d . . .
H2A H 0.5904 0.6917 0.2570 0.031 Uiso 1 1 calc R . .
H2B H 0.6266 0.5494 0.2569 0.031 Uiso 1 1 calc R . .
C1 C 0.6610(2) 1.0641(3) 0.1423(3) 0.0247(7) Uani 1 1 d . . .
H1A H 0.6746 1.0635 0.0610 0.030 Uiso 1 1 calc R . .
H1B H 0.6124 1.1352 0.1566 0.030 Uiso 1 1 calc R . .
C2 C 0.6200(2) 0.9264(3) 0.1759(2) 0.0216(6) Uani 1 1 d . . .
C3 C 0.5156(2) 0.5729(2) 0.3584(4) 0.0310(7) Uani 1 1 d . . .
H3A H 0.4587 0.6328 0.3607 0.037 Uiso 1 1 calc R . .
H3B H 0.5548 0.5914 0.4257 0.037 Uiso 1 1 calc R . .
C4 C 0.5163(2) 0.5734(3) 0.1544(2) 0.0237(7) Uani 1 1 d . . .
H4A H 0.5563 0.5911 0.0876 0.028 Uiso 1 1 calc R . .
H4B H 0.4599 0.6342 0.1512 0.028 Uiso 1 1 calc R . .


_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
Sn1 O1 2.0894(19) . ?
Sn1 O1 2.0894(19) 3_655 ?
Sn1 N1 2.222(3) . ?
Sn1 Cl2 2.3510(10) . ?
Sn1 Cl1 2.3670(8) 3_655 ?
Sn1 Cl1 2.3670(8) . ?
O1 C2 1.307(3) . ?
O2 C2 1.204(3) . ?
N1 C1 1.483(3) . ?
N1 C1 1.483(3) 3_655 ?
N1 H1 0.9300 . ?
N2 C4 1.477(3) . ?
N2 C3 1.476(5) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
C1 C2 1.525(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C3 1.498(5) 2_665 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C4 1.515(5) 2_665 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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 Sn1 O1 83.82(11) . 3_655 ?
O1 Sn1 N1 78.32(7) . . ?
O1 Sn1 N1 78.32(7) 3_655 . ?
O1 Sn1 Cl2 89.74(5) . . ?
O1 Sn1 Cl2 89.74(5) 3_655 . ?
N1 Sn1 Cl2 163.87(8) . . ?
O1 Sn1 Cl1 168.43(6) . 3_655 ?
O1 Sn1 Cl1 89.56(6) 3_655 3_655 ?
N1 Sn1 Cl1 91.08(5) . 3_655 ?
Cl2 Sn1 Cl1 99.73(3) . 3_655 ?
O1 Sn1 Cl1 89.56(6) . . ?
O1 Sn1 Cl1 168.43(6) 3_655 . ?
N1 Sn1 Cl1 91.08(5) . . ?
Cl2 Sn1 Cl1 99.73(3) . . ?
Cl1 Sn1 Cl1 95.30(5) 3_655 . ?
C2 O1 Sn1 118.86(16) . . ?
C1 N1 C1 113.9(3) . 3_655 ?
C1 N1 Sn1 108.00(16) . . ?
C1 N1 Sn1 108.00(16) 3_655 . ?
C1 N1 H1 109.0 . . ?
C1 N1 H1 109.0 3_655 . ?
Sn1 N1 H1 109.0 . . ?
C4 N2 C3 111.2(2) . . ?
C4 N2 H2A 109.4 . . ?
C3 N2 H2A 109.4 . . ?
C4 N2 H2B 109.4 . . ?
C3 N2 H2B 109.4 . . ?
H2A N2 H2B 108.0 . . ?
N1 C1 C2 113.1(2) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
O2 C2 O1 123.0(3) . . ?
O2 C2 C1 120.6(2) . . ?
O1 C2 C1 116.4(2) . . ?
N2 C3 C3 109.92(18) . 2_665 ?
N2 C3 H3A 109.7 . . ?
C3 C3 H3A 109.7 2_665 . ?
N2 C3 H3B 109.7 . . ?
C3 C3 H3B 109.7 2_665 . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C4 109.86(19) . 2_665 ?
N2 C4 H4A 109.7 . . ?
C4 C4 H4A 109.7 2_665 . ?
N2 C4 H4B 109.7 . . ?
C4 C4 H4B 109.7 2_665 . ?
H4A C4 H4B 108.2 . . ?

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
O1 Sn1 O1 C2 -89.92(18) 3_655 . . . ?
N1 Sn1 O1 C2 -10.61(18) . . . . ?
Cl2 Sn1 O1 C2 -179.69(18) . . . . ?
Cl1 Sn1 O1 C2 -34.5(4) 3_655 . . . ?
Cl1 Sn1 O1 C2 80.58(18) . . . . ?
O1 Sn1 N1 C1 18.78(18) . . . . ?
O1 Sn1 N1 C1 104.79(19) 3_655 . . . ?
Cl2 Sn1 N1 C1 61.79(18) . . . . ?
Cl1 Sn1 N1 C1 -165.88(18) 3_655 . . . ?
Cl1 Sn1 N1 C1 -70.55(18) . . . . ?
O1 Sn1 N1 C1 -104.79(19) . . . 3_655 ?
O1 Sn1 N1 C1 -18.78(18) 3_655 . . 3_655 ?
Cl2 Sn1 N1 C1 -61.79(18) . . . 3_655 ?
Cl1 Sn1 N1 C1 70.55(18) 3_655 . . 3_655 ?
Cl1 Sn1 N1 C1 165.88(18) . . . 3_655 ?
C1 N1 C1 C2 95.3(3) 3_655 . . . ?
Sn1 N1 C1 C2 -24.6(3) . . . . ?
Sn1 O1 C2 O2 -179.4(2) . . . . ?
Sn1 O1 C2 C1 -0.5(3) . . . . ?
N1 C1 C2 O2 -163.0(3) . . . . ?
N1 C1 C2 O1 18.1(4) . . . . ?
C4 N2 C3 C3 58.5(3) . . . 2_665 ?
C3 N2 C4 C4 -57.7(3) . . . 2_665 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.061
