# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
#TrackingRef '- Complex 2c.cif'

_audit_creation_method           maXus
_publ_contact_author_name        'Khamphee Phomphrai'
_publ_contact_author_address     
;
Center for Catalysis, Department of Chemistry and
Center of Excellence for Innovation in Chemistry,
Faculty of Science, Mahidol University,
Rama 6 Road, Bangkok 10400 Thailand.
;
_publ_contact_author_email       khamphee.pho@mahidol.ac.th
_publ_contact_author_fax         ' '
_publ_contact_author_phone       ' '
_publ_section_title              
;

;
_publ_author_address             
;
Chemistry Department, Mahidol University, Bangkok, Thailand 10400
;
_publ_section_abstract           
;
We present the crystal and molecular structure of
;
_publ_section_comment            
;
The study of the titled structure was undertaken to establish its three
dimensional structure. Geometries are tabulated below. All diagrams and
calculations were performed using maXus (Bruker Nonius, Delft & MacScience,
Japan).
;
_publ_section_synopsis           
;

;
_publ_section_exptl_prep         
;

;
_publ_section_exptl_refinement   
;

;
_publ_section_figure_captions    
;

;
_publ_section_acknowledgements   
;

;
_publ_author_name                'Khamphee Phomphrai'

data_compound
_database_code_depnum_ccdc_archive 'CCDC 893746'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H44 N2 O2 Sn'
_chemical_formula_sum            'C38 H44 N2 O2 Sn'
_chemical_compound_source        Synthesis
_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_diffrn_ambient_temperature      150(2)
_cell_measurement_temperature    150

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10

_diffrn_measurement_device       KappaCCD
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ' MoK\a'

loop_
_diffrn_radiation_wavelength
0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_radiation_wavelength_id  all

_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.02415
_diffrn_orient_matrix_UB_12      0.11054
_diffrn_orient_matrix_UB_13      0.00732
_diffrn_orient_matrix_UB_21      0.00195
_diffrn_orient_matrix_UB_22      0.00340
_diffrn_orient_matrix_UB_23      -0.05780
_diffrn_orient_matrix_UB_31      -0.04197
_diffrn_orient_matrix_UB_32      0.00998
_diffrn_orient_matrix_UB_33      -0.00083

_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_special_details           
;
?
;
_chemical_formula_weight         679.472
_exptl_crystal_F_000             1408

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

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration unk
_cell_length_a                   8.8207(4)
_cell_length_b                   17.2625(5)
_cell_length_c                   23.1793(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.977(2)
_cell_angle_gamma                90.00
_cell_volume                     3528.9(2)
_diffrn_reflns_number            7069
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_full        28.71
_cell_measurement_reflns_used    3353
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      28.700
_diffrn_measurement_method       CCD
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

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'

_exptl_absorpt_coefficient_mu    0.757
_reflns_number_total             4373
_reflns_number_gt                3455
_reflns_threshold_expression     >2sigma(I)

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.067
_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^)+(0.0313P)^2^+5.5585P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4373
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.0000 0.457840(14) 0.2500 0.04265(10) Uani 1 2 d S . .
O1 O 0.1695(2) 0.53816(11) 0.24109(10) 0.0541(5) Uani 1 1 d . . .
N1 N -0.0345(3) 0.49684(12) 0.14779(10) 0.0410(5) Uani 1 1 d . . .
C8 C -0.1164(3) 0.45006(15) 0.10650(12) 0.0431(6) Uani 1 1 d . . .
C13 C -0.2718(4) 0.46226(17) 0.09671(14) 0.0505(7) Uani 1 1 d . . .
C7 C 0.0065(3) 0.56365(16) 0.13040(13) 0.0479(7) Uani 1 1 d . . .
H7 H -0.0212 0.5805 0.0922 0.057 Uiso 1 1 d R . .
C9 C -0.0377(4) 0.39228(17) 0.07715(14) 0.0517(7) Uani 1 1 d . . .
C6 C 0.0950(4) 0.62068(16) 0.16193(13) 0.0484(7) Uani 1 1 d . . .
C17 C -0.3645(4) 0.5175(2) 0.13306(16) 0.0624(9) Uani 1 1 d . . .
H17 H -0.2943 0.5454 0.1574 0.075 Uiso 1 1 d R . .
C12 C -0.3423(4) 0.4188(2) 0.05325(16) 0.0633(9) Uani 1 1 d . . .
H12 H -0.4475 0.4279 0.0444 0.076 Uiso 1 1 d R . .
C10 C -0.1155(4) 0.35011(19) 0.03497(16) 0.0615(9) Uani 1 1 d . . .
H10 H -0.0623 0.3099 0.0150 0.074 Uiso 1 1 d R . .
C14 C 0.1282(4) 0.3755(2) 0.08996(17) 0.0672(10) Uani 1 1 d . . .
H14 H 0.1626 0.4155 0.1158 0.081 Uiso 1 1 d R . .
C11 C -0.2648(4) 0.3644(2) 0.02226(16) 0.0663(9) Uani 1 1 d . . .
H11 H -0.3147 0.3359 -0.0082 0.080 Uiso 1 1 d R . .
C2 C 0.2620(4) 0.6649(2) 0.23875(17) 0.0719(11) Uani 1 1 d . . .
H2 H 0.3123 0.6573 0.2754 0.086 Uiso 1 1 d R . .
C1 C 0.1717(3) 0.60583(17) 0.21438(13) 0.0489(7) Uani 1 1 d . . .
C5 C 0.1098(5) 0.69394(19) 0.13638(17) 0.0717(10) Uani 1 1 d . . .
H5 H 0.0549 0.7056 0.1013 0.086 Uiso 1 1 d R . .
C15 C 0.1500(6) 0.2975(3) 0.1172(3) 0.141(2) Uani 1 1 d . . .
H15A H 0.2558 0.2887 0.1251 0.169 Uiso 1 1 d R . .
H15B H 0.1117 0.2576 0.0921 0.169 Uiso 1 1 d R . .
H15C H 0.0955 0.2966 0.1527 0.169 Uiso 1 1 d R . .
C4 C 0.1961(6) 0.7510(2) 0.1615(2) 0.0919(15) Uani 1 1 d . . .
H4 H 0.2051 0.8007 0.1432 0.110 Uiso 1 1 d R . .
C3 C 0.2713(6) 0.7360(2) 0.2126(2) 0.0930(15) Uani 1 1 d . . .
H3 H 0.3366 0.7753 0.2286 0.112 Uiso 1 1 d R . .
C18 C -0.4754(6) 0.4729(3) 0.1697(2) 0.1053(16) Uani 1 1 d . . .
H18A H -0.5334 0.5085 0.1922 0.126 Uiso 1 1 d R . .
H18B H -0.4197 0.4387 0.1950 0.126 Uiso 1 1 d R . .
H18C H -0.5425 0.4431 0.1454 0.126 Uiso 1 1 d R . .
C19 C -0.4500(6) 0.5772(3) 0.0980(2) 0.1107(18) Uani 1 1 d . . .
H19A H -0.5059 0.6106 0.1230 0.133 Uiso 1 1 d R . .
H19B H -0.5189 0.5512 0.0720 0.133 Uiso 1 1 d R . .
H19C H -0.3798 0.6075 0.0762 0.133 Uiso 1 1 d R . .
C16 C 0.2222(6) 0.3805(5) 0.0372(3) 0.155(3) Uani 1 1 d . . .
H16A H 0.3264 0.3698 0.0469 0.187 Uiso 1 1 d R . .
H16B H 0.2135 0.4319 0.0218 0.187 Uiso 1 1 d R . .
H16C H 0.1866 0.3438 0.0090 0.187 Uiso 1 1 d 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 0.05417(18) 0.03091(14) 0.04269(16) 0.000 -0.00402(11) 0.000
O1 0.0563(12) 0.0569(12) 0.0486(13) 0.0121(10) -0.0157(10) -0.0156(10)
N1 0.0489(13) 0.0375(11) 0.0363(13) -0.0030(9) -0.0065(10) -0.0064(9)
C8 0.0534(16) 0.0410(14) 0.0346(14) -0.0003(11) -0.0048(12) -0.0095(12)
C13 0.0549(17) 0.0562(17) 0.0402(16) -0.0042(13) -0.0077(13) -0.0065(14)
C7 0.0594(18) 0.0478(15) 0.0362(15) 0.0040(12) -0.0091(13) -0.0081(13)
C9 0.0588(19) 0.0487(16) 0.0474(18) -0.0076(13) -0.0040(14) -0.0078(13)
C6 0.0622(19) 0.0410(14) 0.0417(16) 0.0010(12) -0.0032(14) -0.0103(13)
C17 0.0526(19) 0.081(2) 0.053(2) -0.0097(17) -0.0079(15) 0.0026(16)
C12 0.057(2) 0.077(2) 0.056(2) -0.0072(18) -0.0131(16) -0.0139(17)
C10 0.071(2) 0.0568(19) 0.057(2) -0.0163(16) -0.0040(17) -0.0063(16)
C14 0.062(2) 0.069(2) 0.070(3) -0.0241(19) -0.0036(18) 0.0019(17)
C11 0.075(2) 0.066(2) 0.058(2) -0.0201(17) -0.0144(18) -0.0168(18)
C2 0.089(3) 0.071(2) 0.054(2) 0.0027(17) -0.0190(19) -0.0380(19)
C1 0.0546(18) 0.0497(16) 0.0424(17) -0.0024(13) 0.0007(13) -0.0138(13)
C5 0.106(3) 0.0540(19) 0.055(2) 0.0101(16) -0.012(2) -0.0189(19)
C15 0.104(4) 0.128(5) 0.189(7) 0.036(5) -0.016(4) 0.038(4)
C4 0.146(4) 0.051(2) 0.079(3) 0.009(2) -0.010(3) -0.040(2)
C3 0.133(4) 0.070(2) 0.076(3) -0.004(2) -0.012(3) -0.057(3)
C18 0.108(4) 0.130(4) 0.078(4) -0.002(3) 0.032(3) 0.004(3)
C19 0.145(5) 0.108(4) 0.080(4) -0.002(3) 0.002(3) 0.055(3)
C16 0.071(3) 0.289(9) 0.108(5) -0.014(5) 0.017(3) -0.040(4)

_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 2.0524(19) 2 ?
Sn1 O1 2.0524(19) . ?
Sn1 N1 2.477(2) 2 ?
Sn1 N1 2.477(2) . ?
O1 C1 1.323(3) . ?
N1 C7 1.276(3) . ?
N1 C8 1.438(3) . ?
C8 C9 1.398(4) . ?
C8 C13 1.402(4) . ?
C13 C12 1.394(4) . ?
C13 C17 1.520(5) . ?
C7 C6 1.447(4) . ?
C7 H7 0.9600 . ?
C9 C10 1.391(4) . ?
C9 C14 1.516(5) . ?
C6 C5 1.404(4) . ?
C6 C1 1.405(4) . ?
C17 C19 1.507(6) . ?
C17 C18 1.516(6) . ?
C17 H17 0.9601 . ?
C12 C11 1.372(5) . ?
C12 H12 0.9601 . ?
C10 C11 1.367(5) . ?
C10 H10 0.9599 . ?
C14 C16 1.491(6) . ?
C14 C15 1.497(6) . ?
C14 H14 0.9602 . ?
C11 H11 0.9601 . ?
C2 C3 1.371(5) . ?
C2 C1 1.407(4) . ?
C2 H2 0.9600 . ?
C5 C4 1.369(5) . ?
C5 H5 0.9601 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9599 . ?
C15 H15C 0.9599 . ?
C4 C3 1.373(6) . ?
C4 H4 0.9600 . ?
C3 H3 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9601 . ?
C18 H18C 0.9598 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9601 . ?
C19 H19C 0.9602 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9601 . ?

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 95.00(12) 2 . ?
O1 Sn1 N1 78.35(8) 2 2 ?
O1 Sn1 N1 80.48(8) . 2 ?
O1 Sn1 N1 80.48(8) 2 . ?
O1 Sn1 N1 78.35(8) . . ?
N1 Sn1 N1 148.45(10) 2 . ?
C1 O1 Sn1 131.33(19) . . ?
C7 N1 C8 116.1(2) . . ?
C7 N1 Sn1 121.14(18) . . ?
C8 N1 Sn1 122.44(16) . . ?
C9 C8 C13 121.4(3) . . ?
C9 C8 N1 118.5(3) . . ?
C13 C8 N1 120.1(3) . . ?
C12 C13 C8 117.3(3) . . ?
C12 C13 C17 120.0(3) . . ?
C8 C13 C17 122.6(3) . . ?
N1 C7 C6 127.5(3) . . ?
N1 C7 H7 119.7 . . ?
C6 C7 H7 112.8 . . ?
C10 C9 C8 118.2(3) . . ?
C10 C9 C14 120.0(3) . . ?
C8 C9 C14 121.8(3) . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 117.0(3) . . ?
C1 C6 C7 124.1(3) . . ?
C19 C17 C18 109.2(4) . . ?
C19 C17 C13 113.5(3) . . ?
C18 C17 C13 110.5(3) . . ?
C19 C17 H17 106.6 . . ?
C18 C17 H17 109.9 . . ?
C13 C17 H17 107.0 . . ?
C11 C12 C13 121.8(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 118.9 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 118.5 . . ?
C16 C14 C15 109.2(5) . . ?
C16 C14 C9 112.1(4) . . ?
C15 C14 C9 111.8(3) . . ?
C16 C14 H14 107.1 . . ?
C15 C14 H14 110.3 . . ?
C9 C14 H14 106.1 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 120.5 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 120.3 . . ?
O1 C1 C6 123.7(3) . . ?
O1 C1 C2 117.7(3) . . ?
C6 C1 C2 118.5(3) . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 119.8 . . ?
C14 C15 H15A 109.9 . . ?
C14 C15 H15B 110.3 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 108.2 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.5 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 118.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.9 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 110.0 . . ?
C17 C19 H19B 108.9 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.6 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.4 . . ?
C14 C16 H16A 110.0 . . ?
C14 C16 H16B 108.4 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.9 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?