# 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_h14kcm7
_audit_block_doi                 10.5517/cc1j0hkl
_database_code_depnum_ccdc_archive 'CCDC 1400659'
_audit_update_record             
;
2015-05-13 deposited with the CCDC.
2015-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H30 O6 P2 Sn'
_chemical_formula_sum            'C12 H30 O6 P2 Sn'
_chemical_formula_weight         451.01

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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.2504(4)
_cell_length_b                   8.6355(7)
_cell_length_c                   10.3202(8)
_cell_angle_alpha                86.763(5)
_cell_angle_beta                 85.077(5)
_cell_angle_gamma                82.392(4)
_cell_volume                     461.60(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14792
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      30.034

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             230
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.577
_shelx_estimated_absorpt_T_min   0.451
_shelx_estimated_absorpt_T_max   0.743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  0.729
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_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  'Nonius Kappa CCD'
_diffrn_measurement_method       '270 2.0 degree images with φ and ω scans'
_diffrn_reflns_number            8779
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.968
_diffrn_reflns_theta_max         30.013
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2708
_reflns_number_gt                2125
_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2013 (Sheldrick, 2013)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'SHELXL-2013 (Sheldrick, 2013)
;

_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)+(0.0358P)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         2603
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0782
_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_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
Sn Sn 0.0000 1.0000 0.0000 0.01629(11) Uani 1 2 d S . P . .
P P 0.56166(14) 0.79793(9) -0.14438(8) 0.01536(18) Uani 1 1 d . . . . .
O1 O 0.2981(4) 0.8899(2) -0.1411(2) 0.0184(5) Uani 1 1 d . . . . .
O2 O 0.5410(4) 0.6169(2) -0.1176(2) 0.0228(5) Uani 1 1 d . . . . .
O3 O 0.7397(4) 0.8347(2) -0.0476(2) 0.0205(5) Uani 1 1 d . . . . .
C1 C 0.7068(7) 0.8169(4) -0.3057(3) 0.0299(8) Uani 1 1 d . . . . .
H1A H 0.8832 0.7627 -0.3099 0.045 Uiso 1 1 calc R U . . .
H1B H 0.7104 0.9279 -0.3304 0.045 Uiso 1 1 calc R U . . .
H1C H 0.6066 0.7706 -0.3658 0.045 Uiso 1 1 calc R U . . .
C2 C 0.3324(7) 0.5474(4) -0.1631(4) 0.0297(8) Uani 1 1 d . . . . .
H2A H 0.3435 0.4375 -0.1322 0.045 Uiso 1 1 calc R U . . .
H2B H 0.3441 0.5538 -0.2585 0.045 Uiso 1 1 calc R U . . .
H2C H 0.1675 0.6036 -0.1296 0.045 Uiso 1 1 calc R U . . .
C3 C 0.1301(6) 0.8299(4) 0.1462(3) 0.0182(7) Uani 1 1 d . . . . .
H3A H 0.1776 0.7282 0.1050 0.022 Uiso 1 1 calc R U . . .
H3B H 0.2889 0.8600 0.1775 0.022 Uiso 1 1 calc R U . . .
C4 C -0.0584(6) 0.8065(4) 0.2635(3) 0.0208(7) Uani 1 1 d . . . . .
H4A H -0.2240 0.7861 0.2329 0.025 Uiso 1 1 calc R U . . .
H4B H -0.0916 0.9041 0.3115 0.025 Uiso 1 1 calc R U . . .
C5 C 0.0385(6) 0.6719(4) 0.3562(3) 0.0256(8) Uani 1 1 d . . . . .
H5A H -0.1067 0.6467 0.4179 0.031 Uiso 1 1 calc R U . . .
H5B H 0.0986 0.5783 0.3053 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2562(7) 0.7071(5) 0.4327(4) 0.0325(9) Uani 1 1 d . . . . .
H6A H 0.3053 0.6180 0.4924 0.049 Uiso 1 1 calc R U . . .
H6B H 0.1991 0.8004 0.4826 0.049 Uiso 1 1 calc R U . . .
H6C H 0.4049 0.7258 0.3725 0.049 Uiso 1 1 calc R U . . .


_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
Sn C3 2.136(3) . ?
Sn C3 2.136(3) 2_575 ?
Sn O1 2.201(2) . ?
Sn O1 2.201(2) 2_575 ?
Sn O3 2.204(2) 1_455 ?
Sn O3 2.204(2) 2_675 ?
P O3 1.499(2) . ?
P O1 1.500(2) . ?
P O2 1.589(2) . ?
P C1 1.779(3) . ?
O2 C2 1.441(4) . ?
O3 Sn 2.204(2) 1_655 ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.519(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.515(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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
C3 Sn C3 180.00(13) . 2_575 ?
C3 Sn O1 89.56(10) . . ?
C3 Sn O1 90.44(10) 2_575 . ?
C3 Sn O1 90.44(10) . 2_575 ?
C3 Sn O1 89.56(10) 2_575 2_575 ?
O1 Sn O1 180.00(8) . 2_575 ?
C3 Sn O3 86.68(10) . 1_455 ?
C3 Sn O3 93.32(10) 2_575 1_455 ?
O1 Sn O3 89.33(8) . 1_455 ?
O1 Sn O3 90.67(8) 2_575 1_455 ?
C3 Sn O3 93.32(10) . 2_675 ?
C3 Sn O3 86.68(10) 2_575 2_675 ?
O1 Sn O3 90.67(8) . 2_675 ?
O1 Sn O3 89.33(8) 2_575 2_675 ?
O3 Sn O3 180.00(11) 1_455 2_675 ?
O3 P O1 117.48(13) . . ?
O3 P O2 104.34(12) . . ?
O1 P O2 110.43(12) . . ?
O3 P C1 110.55(15) . . ?
O1 P C1 107.55(15) . . ?
O2 P C1 105.93(15) . . ?
P O1 Sn 139.77(13) . . ?
C2 O2 P 120.8(2) . . ?
P O3 Sn 144.84(13) . 1_655 ?
P C1 H1A 109.5 . . ?
P C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
P C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 Sn 116.5(2) . . ?
C4 C3 H3A 108.2 . . ?
Sn C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
Sn C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C3 C4 C5 113.1(3) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 113.5(3) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
O3 P O1 Sn -33.9(2) . . . . ?
O2 P O1 Sn 85.6(2) . . . . ?
C1 P O1 Sn -159.3(2) . . . . ?
O3 P O2 C2 161.5(3) . . . . ?
O1 P O2 C2 34.4(3) . . . . ?
C1 P O2 C2 -81.7(3) . . . . ?
O1 P O3 Sn -77.7(3) . . . 1_655 ?
O2 P O3 Sn 159.7(2) . . . 1_655 ?
C1 P O3 Sn 46.2(3) . . . 1_655 ?
Sn C3 C4 C5 174.1(2) . . . . ?
C3 C4 C5 C6 71.9(4) . . . . ?

_refine_diff_density_max         0.659
_refine_diff_density_min         -1.982
_refine_diff_density_rms         0.163

_shelxl_version_number           2013-4



