# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_global

_audit_creation_method           SHELXL-97

_journal_coden_Cambridge         182

_publ_contact_author_name        'Dr. Andrea Deak'
_publ_contact_author_address     
; Institute of Structural Chemistry
Chemical Research Center,Hungarian Academy of Sciences,
H-1525-Budapest,
P.O.Box 17,
Hungary
;
_publ_contact_author_email       deak@chemres.hu
_publ_contact_author_phone       00-36-1-325-7547
_publ_contact_author_fax         00-36-1-438-4141/201

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Solid-State and Melt Demethylation of the [Me3Sn(PhN2O2)]4 Tetramer into
Dimeric [Me2Sn(PhN2O2)2]2 : A Thermally Induced Methyl-Transfer
between Supramolecules
;

loop_
_publ_author_name
_publ_author_address

'Andrea Deak'
; Institute of Structural Chemistry,
Chemical Research Center,
Hungarian Academy of Sciences,
P.O. Box 17,
H-1525 Budapest,
Hungary
;
'Gabor Tarkanyi'
; Institute of Structural Chemistry,
Chemical Research Center,
Hungarian Academy of Sciences,
P.O. Box 17,
H-1525 Budapest,
Hungary
;

data_complex2
_database_code_depnum_ccdc_archive 'CCDC 272081'

_chemical_name_systematic        
;
Bis[dimethyl(N-nitroso-N-phenylhydroxylaminato)tin(IV)]
;
_chemical_name_common            Bis[dimethyl(cupferronato)tin(IV)]
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 N8 O8 Sn2'
_chemical_formula_sum            'C28 H32 N8 O8 Sn2'
_chemical_formula_weight         846.00
_chemical_compound_source        'obtained from the melt'

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'
Sn Sn -0.6537 1.4246 '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'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.408(3)
_cell_length_b                   9.439(3)
_cell_length_c                   10.739(2)
_cell_angle_alpha                64.31(2)
_cell_angle_beta                 75.94(2)
_cell_angle_gamma                78.00(2)
_cell_volume                     827.9(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      11.66
_cell_measurement_theta_max      14.56

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    1.568
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(DATCOR; Reibenspies, 1989)'
_exptl_absorpt_correction_T_min  0.4697
_exptl_absorpt_correction_T_max  0.7296

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w--2\q
_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            12298
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         32.04
_reflns_number_total             5723
_reflns_number_gt                3364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 Express (Enraf-Nonius, 1992)'
_computing_cell_refinement       'CAD4 Express'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0868P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         5723
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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 0.11666(3) 0.68550(3) 0.44571(3) 0.05716(12) Uani 1 1 d . . .
C8 C -0.0739(6) 0.8375(7) 0.3808(7) 0.0882(16) Uani 1 1 d . . .
H8A H -0.0719 0.8617 0.2839 0.123 Uiso 1 1 calc R . .
H8B H -0.0769 0.9336 0.3921 0.123 Uiso 1 1 calc R . .
H8C H -0.1599 0.7866 0.4367 0.123 Uiso 1 1 calc R . .
C7 C 0.2985(5) 0.5166(8) 0.5029(7) 0.0893(16) Uani 1 1 d . . .
H7A H 0.2746 0.4141 0.5226 0.125 Uiso 1 1 calc R . .
H7B H 0.3233 0.5151 0.5851 0.125 Uiso 1 1 calc R . .
H7C H 0.3810 0.5430 0.4274 0.125 Uiso 1 1 calc R . .
O1B O 0.0624(4) 0.7042(5) 0.6542(3) 0.0846(11) Uani 1 1 d . . .
O2B O -0.0387(3) 0.4973(4) 0.6224(3) 0.0639(7) Uani 1 1 d . . .
N1B N -0.0465(4) 0.6298(4) 0.7440(3) 0.0550(7) Uani 1 1 d . . .
N2B N -0.1018(4) 0.5232(4) 0.7347(3) 0.0532(7) Uani 1 1 d . . .
C1B C -0.1038(5) 0.6690(4) 0.8639(4) 0.0531(8) Uani 1 1 d . . .
C2B C -0.2336(6) 0.6206(6) 0.9470(4) 0.0724(12) Uani 1 1 d . . .
H2B H -0.2868 0.5618 0.9279 0.094 Uiso 1 1 calc R . .
C3B C -0.2848(7) 0.6612(7) 1.0615(5) 0.0876(16) Uani 1 1 d . . .
H3B H -0.3738 0.6298 1.1192 0.114 Uiso 1 1 calc R . .
C4B C -0.2076(8) 0.7449(7) 1.0898(5) 0.0899(17) Uani 1 1 d . . .
H4B H -0.2431 0.7704 1.1672 0.117 Uiso 1 1 calc R . .
C5B C -0.0757(8) 0.7934(7) 1.0047(6) 0.0957(19) Uani 1 1 d . . .
H5B H -0.0216 0.8507 1.0246 0.124 Uiso 1 1 calc R . .
C6B C -0.0254(6) 0.7556(6) 0.8900(5) 0.0756(13) Uani 1 1 d . . .
H6B H 0.0621 0.7894 0.8305 0.098 Uiso 1 1 calc R . .
O1A O 0.2353(4) 0.8819(5) 0.4065(3) 0.0796(10) Uani 1 1 d . . .
O2A O 0.2402(5) 0.7805(5) 0.2213(3) 0.0890(12) Uani 1 1 d . . .
N1A N 0.3293(4) 0.9252(4) 0.2867(3) 0.0615(9) Uani 1 1 d . . .
N2A N 0.3342(5) 0.8769(5) 0.1912(4) 0.0760(11) Uani 1 1 d . . .
C1A C 0.4267(5) 1.0365(5) 0.2628(4) 0.0593(9) Uani 1 1 d . . .
C6A C 0.4109(6) 1.0981(6) 0.3604(5) 0.0787(14) Uani 1 1 d . . .
H6A H 0.3390 1.0669 0.4405 0.102 Uiso 1 1 calc R . .
C3A C 0.5022(8) 1.2069(8) 0.3396(7) 0.100(2) Uani 1 1 d . . .
H3A H 0.4897 1.2522 0.4037 0.130 Uiso 1 1 calc R . .
C4A C 0.6115(7) 1.2473(7) 0.2233(7) 0.0943(18) Uani 1 1 d . . .
H4A H 0.6736 1.3198 0.2090 0.123 Uiso 1 1 calc R . .
C5A C 0.6296(7) 1.1814(8) 0.1285(6) 0.0901(17) Uani 1 1 d . . .
H5A H 0.7042 1.2090 0.0504 0.117 Uiso 1 1 calc R . .
C2A C 0.5373(5) 1.0739(6) 0.1481(5) 0.0716(12) Uani 1 1 d . . .
H2A H 0.5503 1.0278 0.0846 0.093 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
Sn1 0.05966(18) 0.0745(2) 0.04039(14) -0.02366(12) 0.00337(10) -0.02733(13)
C8 0.078(3) 0.074(3) 0.103(4) -0.026(3) -0.018(3) -0.008(3)
C7 0.052(2) 0.109(4) 0.110(5) -0.045(4) -0.016(3) -0.009(3)
O1B 0.095(2) 0.123(3) 0.0545(17) -0.0476(19) 0.0227(16) -0.066(2)
O2B 0.0707(18) 0.0852(19) 0.0451(14) -0.0337(14) 0.0088(12) -0.0339(15)
N1B 0.0609(18) 0.0678(19) 0.0355(14) -0.0187(13) 0.0009(12) -0.0219(15)
N2B 0.0578(17) 0.0633(18) 0.0397(14) -0.0204(14) -0.0015(13) -0.0188(14)
C1B 0.067(2) 0.0524(19) 0.0350(15) -0.0139(14) -0.0108(15) -0.0028(17)
C2B 0.083(3) 0.086(3) 0.046(2) -0.027(2) 0.005(2) -0.023(2)
C3B 0.099(4) 0.098(4) 0.053(3) -0.031(3) 0.013(2) -0.014(3)
C4B 0.137(5) 0.080(3) 0.051(2) -0.034(2) -0.002(3) -0.007(3)
C5B 0.150(6) 0.088(4) 0.067(3) -0.045(3) -0.009(3) -0.032(4)
C6B 0.100(4) 0.076(3) 0.057(2) -0.032(2) -0.002(2) -0.027(3)
O1A 0.098(2) 0.104(2) 0.0491(15) -0.0421(16) 0.0300(15) -0.061(2)
O2A 0.116(3) 0.119(3) 0.0497(17) -0.0439(19) 0.0200(17) -0.068(2)
N1A 0.073(2) 0.075(2) 0.0383(15) -0.0226(15) 0.0111(14) -0.0362(18)
N2A 0.097(3) 0.091(3) 0.0440(18) -0.0302(18) 0.0183(18) -0.049(2)
C1A 0.070(2) 0.062(2) 0.0401(17) -0.0150(16) 0.0060(16) -0.0282(19)
C6A 0.095(4) 0.079(3) 0.066(3) -0.038(2) 0.017(2) -0.036(3)
C3A 0.123(5) 0.097(4) 0.105(5) -0.062(4) 0.012(4) -0.052(4)
C4A 0.099(4) 0.092(4) 0.090(4) -0.031(3) 0.011(3) -0.052(3)
C5A 0.081(3) 0.112(4) 0.074(3) -0.036(3) 0.021(3) -0.050(3)
C2A 0.067(3) 0.092(3) 0.054(2) -0.030(2) 0.0105(19) -0.029(2)

_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 C7 2.091(6) . ?
Sn1 C8 2.105(6) . ?
Sn1 O1A 2.194(3) . ?
Sn1 O1B 2.248(3) . ?
Sn1 O2A 2.272(3) . ?
Sn1 O2B 2.388(3) . ?
Sn1 O2B 2.435(3) 2_566 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1B N1B 1.305(4) . ?
O2B N2B 1.309(4) . ?
O2B Sn1 2.435(3) 2_566 ?
N1B N2B 1.274(5) . ?
N1B C1B 1.442(5) . ?
C1B C6B 1.356(6) . ?
C1B C2B 1.359(6) . ?
C2B C3B 1.391(7) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.341(9) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.381(9) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.377(7) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
O1A N1A 1.321(4) . ?
O2A N2A 1.286(5) . ?
N1A N2A 1.279(5) . ?
N1A C1A 1.435(5) . ?
C1A C6A 1.370(6) . ?
C1A C2A 1.370(5) . ?
C6A C3A 1.385(7) . ?
C6A H6A 0.9300 . ?
C3A C4A 1.374(8) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.370(9) . ?
C4A H4A 0.9300 . ?
C5A C2A 1.385(7) . ?
C5A H5A 0.9300 . ?
C2A H2A 0.9300 . ?

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
C7 Sn1 C8 173.4(2) . . ?
C7 Sn1 O1A 93.0(2) . . ?
C8 Sn1 O1A 92.9(2) . . ?
C7 Sn1 O1B 92.4(2) . . ?
C8 Sn1 O1B 91.9(2) . . ?
O1A Sn1 O1B 77.31(11) . . ?
C7 Sn1 O2A 88.9(2) . . ?
C8 Sn1 O2A 90.3(2) . . ?
O1A Sn1 O2A 69.33(12) . . ?
O1B Sn1 O2A 146.63(13) . . ?
C7 Sn1 O2B 88.4(2) . . ?
C8 Sn1 O2B 88.71(19) . . ?
O1A Sn1 O2B 143.03(10) . . ?
O1B Sn1 O2B 65.72(10) . . ?
O2A Sn1 O2B 147.64(11) . . ?
C7 Sn1 O2B 86.5(2) . 2_566 ?
C8 Sn1 O2B 86.8(2) . 2_566 ?
O1A Sn1 O2B 153.63(10) . 2_566 ?
O1B Sn1 O2B 129.06(10) . 2_566 ?
O2A Sn1 O2B 84.30(11) . 2_566 ?
O2B Sn1 O2B 63.34(11) . 2_566 ?
Sn1 C8 H8A 109.5 . . ?
Sn1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Sn1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Sn1 C7 H7A 109.5 . . ?
Sn1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Sn1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1B O1B Sn1 116.5(2) . . ?
N2B O2B Sn1 117.4(2) . . ?
N2B O2B Sn1 124.0(2) . 2_566 ?
Sn1 O2B Sn1 116.66(11) . 2_566 ?
N2B N1B O1B 124.7(3) . . ?
N2B N1B C1B 118.5(3) . . ?
O1B N1B C1B 116.8(3) . . ?
N1B N2B O2B 112.3(3) . . ?
C6B C1B C2B 121.5(4) . . ?
C6B C1B N1B 118.3(4) . . ?
C2B C1B N1B 120.2(4) . . ?
C1B C2B C3B 118.3(5) . . ?
C1B C2B H2B 120.9 . . ?
C3B C2B H2B 120.9 . . ?
C4B C3B C2B 120.9(5) . . ?
C4B C3B H3B 119.5 . . ?
C2B C3B H3B 119.5 . . ?
C3B C4B C5B 120.3(5) . . ?
C3B C4B H4B 119.8 . . ?
C5B C4B H4B 119.8 . . ?
C6B C5B C4B 119.1(5) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
C1B C6B C5B 119.9(5) . . ?
C1B C6B H6B 120.1 . . ?
C5B C6B H6B 120.1 . . ?
N1A O1A Sn1 113.9(2) . . ?
N2A O2A Sn1 116.9(3) . . ?
N2A N1A O1A 123.5(3) . . ?
N2A N1A C1A 119.2(3) . . ?
O1A N1A C1A 117.3(3) . . ?
N1A N2A O2A 114.5(3) . . ?
C6A C1A C2A 121.0(4) . . ?
C6A C1A N1A 118.5(4) . . ?
C2A C1A N1A 120.4(4) . . ?
C1A C6A C3A 119.8(5) . . ?
C1A C6A H6A 120.1 . . ?
C3A C6A H6A 120.1 . . ?
C4A C3A C6A 119.4(5) . . ?
C4A C3A H3A 120.3 . . ?
C6A C3A H3A 120.3 . . ?
C5A C4A C3A 120.4(5) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C4A C5A C2A 120.4(5) . . ?
C4A C5A H5A 119.8 . . ?
C2A C5A H5A 119.8 . . ?
C1A C2A C5A 118.9(5) . . ?
C1A C2A H2A 120.5 . . ?
C5A C2A H2A 120.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2A H2A N2A 0.93 2.70 3.403(6) 133.0 2_675

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        32.04
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.071
_refine_diff_density_min         -1.374
_refine_diff_density_rms         0.146