# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#
#                 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 
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data_h11alj14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H30 N4 O2 Sn'
_chemical_formula_weight         405.11

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

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

_cell_length_a                   8.6700(3)
_cell_length_b                   9.4020(3)
_cell_length_c                   12.4160(3)
_cell_angle_alpha                79.878(2)
_cell_angle_beta                 84.754(2)
_cell_angle_gamma                70.462(2)
_cell_volume                     938.39(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14456
_cell_measurement_theta_min      7.87
_cell_measurement_theta_max      30.51

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    1.371
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7256
_exptl_absorpt_correction_T_max  0.9346
_exptl_absorpt_process_details   '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  'Bruker Kappa CCD Diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14456
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         7.87
_diffrn_reflns_theta_max         30.51
_reflns_number_total             5596
_reflns_number_gt                5118
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Kappa CCD'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0237P)^2^+0.3245P] 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         5596
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0556
_refine_ls_wR_factor_gt          0.0539
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.020042(12) 0.223476(11) -0.127376(8) 0.02237(4) Uani 1 1 d . . .
N1 N 0.21511(18) 0.25442(17) -0.43267(12) 0.0293(3) Uani 1 1 d . . .
N2 N -0.17034(18) 0.48888(15) -0.13146(11) 0.0267(3) Uani 1 1 d . . .
N11 N 0.13810(16) 0.09925(14) -0.27456(11) 0.0219(2) Uani 1 1 d . . .
N21 N -0.22790(16) 0.29324(14) -0.18395(11) 0.0227(2) Uani 1 1 d . . .
O11 O 0.09242(14) 0.34631(12) -0.27719(10) 0.0262(2) Uani 1 1 d . . .
O21 O -0.38735(18) 0.54208(14) -0.24930(12) 0.0416(3) Uani 1 1 d . . .
C1 C 0.2447(2) 0.4002(2) -0.46899(18) 0.0399(4) Uani 1 1 d . . .
H1A H 0.1440 0.4773 -0.4982 0.060 Uiso 1 1 calc R . .
H1B H 0.3317 0.3877 -0.5263 0.060 Uiso 1 1 calc R . .
H1C H 0.2780 0.4332 -0.4069 0.060 Uiso 1 1 calc R . .
C2 C 0.1714(2) 0.1910(2) -0.51984(15) 0.0378(4) Uani 1 1 d . . .
H2A H 0.1399 0.1012 -0.4882 0.057 Uiso 1 1 calc R . .
H2B H 0.2656 0.1612 -0.5708 0.057 Uiso 1 1 calc R . .
H2C H 0.0794 0.2681 -0.5592 0.057 Uiso 1 1 calc R . .
C3 C -0.2541(3) 0.5161(2) -0.02476(15) 0.0372(4) Uani 1 1 d . . .
H3A H -0.1810 0.5352 0.0226 0.056 Uiso 1 1 calc R . .
H3B H -0.2835 0.4262 0.0096 0.056 Uiso 1 1 calc R . .
H3C H -0.3535 0.6051 -0.0354 0.056 Uiso 1 1 calc R . .
C4 C -0.1325(3) 0.6260(2) -0.18646(16) 0.0373(4) Uani 1 1 d . . .
H4A H -0.2347 0.7105 -0.2019 0.056 Uiso 1 1 calc R . .
H4B H -0.0708 0.6047 -0.2553 0.056 Uiso 1 1 calc R . .
H4C H -0.0667 0.6539 -0.1388 0.056 Uiso 1 1 calc R . .
C11 C 0.15026(18) 0.22906(17) -0.32921(13) 0.0223(3) Uani 1 1 d . . .
C12 C 0.2448(2) -0.05933(18) -0.28386(14) 0.0270(3) Uani 1 1 d . . .
C13 C 0.4109(2) -0.0711(2) -0.34220(16) 0.0316(3) Uani 1 1 d . . .
H13A H 0.3953 -0.0338 -0.4206 0.047 Uiso 1 1 calc R . .
H13B H 0.4819 -0.1780 -0.3318 0.047 Uiso 1 1 calc R . .
H13C H 0.4619 -0.0091 -0.3116 0.047 Uiso 1 1 calc R . .
C14 C 0.1585(3) -0.1450(2) -0.3383(2) 0.0464(5) Uani 1 1 d . . .
H14A H 0.0534 -0.1398 -0.2998 0.070 Uiso 1 1 calc R . .
H14B H 0.2275 -0.2521 -0.3351 0.070 Uiso 1 1 calc R . .
H14C H 0.1395 -0.0979 -0.4150 0.070 Uiso 1 1 calc R . .
C15 C 0.2785(3) -0.1395(2) -0.16598(17) 0.0465(5) Uani 1 1 d . . .
H15A H 0.3377 -0.0892 -0.1304 0.070 Uiso 1 1 calc R . .
H15B H 0.3448 -0.2468 -0.1662 0.070 Uiso 1 1 calc R . .
H15C H 0.1744 -0.1340 -0.1258 0.070 Uiso 1 1 calc R . .
C21 C -0.2768(2) 0.44522(18) -0.19724(13) 0.0264(3) Uani 1 1 d . . .
C22 C -0.32209(19) 0.21215(18) -0.22758(14) 0.0246(3) Uani 1 1 d . . .
C23 C -0.3054(3) 0.2322(2) -0.35221(15) 0.0357(4) Uani 1 1 d . . .
H23A H -0.3523 0.3406 -0.3823 0.053 Uiso 1 1 calc R . .
H23B H -0.3638 0.1736 -0.3797 0.053 Uiso 1 1 calc R . .
H23C H -0.1893 0.1952 -0.3747 0.053 Uiso 1 1 calc R . .
C24 C -0.2500(2) 0.0437(2) -0.17865(18) 0.0357(4) Uani 1 1 d . . .
H24A H -0.1329 0.0067 -0.1985 0.054 Uiso 1 1 calc R . .
H24B H -0.3060 -0.0159 -0.2073 0.054 Uiso 1 1 calc R . .
H24C H -0.2648 0.0324 -0.0988 0.054 Uiso 1 1 calc R . .
C25 C -0.5025(2) 0.2680(2) -0.18956(18) 0.0384(4) Uani 1 1 d . . .
H25A H -0.5103 0.2569 -0.1095 0.058 Uiso 1 1 calc R . .
H25B H -0.5607 0.2070 -0.2143 0.058 Uiso 1 1 calc R . .
H25C H -0.5520 0.3757 -0.2206 0.058 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 0.02637(6) 0.01896(5) 0.01994(6) -0.00223(3) -0.00272(4) -0.00484(4)
N1 0.0309(7) 0.0278(7) 0.0262(7) 0.0018(5) 0.0031(5) -0.0097(6)
N2 0.0371(7) 0.0176(6) 0.0248(6) -0.0054(5) -0.0023(5) -0.0067(5)
N11 0.0228(6) 0.0195(6) 0.0230(6) -0.0032(4) 0.0021(5) -0.0070(5)
N21 0.0239(6) 0.0167(5) 0.0252(6) -0.0048(4) -0.0011(5) -0.0029(5)
O11 0.0286(5) 0.0192(5) 0.0296(6) -0.0024(4) 0.0018(4) -0.0078(4)
O21 0.0467(8) 0.0215(6) 0.0501(8) -0.0052(5) -0.0200(6) 0.0020(5)
C1 0.0358(9) 0.0324(9) 0.0432(11) 0.0096(8) 0.0077(8) -0.0102(7)
C2 0.0368(9) 0.0466(11) 0.0241(8) -0.0042(7) 0.0008(7) -0.0071(8)
C3 0.0480(11) 0.0334(9) 0.0285(9) -0.0138(7) 0.0021(8) -0.0073(8)
C4 0.0559(11) 0.0193(7) 0.0375(10) -0.0009(6) -0.0079(8) -0.0134(8)
C11 0.0190(6) 0.0229(7) 0.0237(7) -0.0018(5) -0.0003(5) -0.0061(5)
C12 0.0292(7) 0.0190(7) 0.0312(8) -0.0061(6) 0.0068(6) -0.0067(6)
C13 0.0258(7) 0.0262(8) 0.0389(10) -0.0037(6) 0.0039(7) -0.0052(6)
C14 0.0444(11) 0.0368(10) 0.0680(14) -0.0275(10) 0.0177(10) -0.0215(9)
C15 0.0591(13) 0.0226(8) 0.0373(10) 0.0052(7) 0.0125(9) 0.0052(8)
C21 0.0310(8) 0.0195(7) 0.0261(8) -0.0063(5) -0.0019(6) -0.0031(6)
C22 0.0228(7) 0.0219(7) 0.0289(8) -0.0070(6) 0.0004(6) -0.0059(5)
C23 0.0451(10) 0.0406(10) 0.0283(9) -0.0106(7) 0.0003(7) -0.0209(8)
C24 0.0331(9) 0.0218(7) 0.0532(11) -0.0042(7) -0.0053(8) -0.0099(7)
C25 0.0254(8) 0.0408(10) 0.0503(12) -0.0182(8) 0.0042(7) -0.0083(7)

_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 O11 2.1688(11) . ?
Sn1 N21 2.1715(13) . ?
Sn1 N11 2.3151(13) . ?
Sn1 N2 2.4839(13) . ?
N1 C11 1.369(2) . ?
N1 C2 1.457(3) . ?
N1 C1 1.464(2) . ?
N2 C3 1.472(2) . ?
N2 C4 1.472(2) . ?
N2 C21 1.482(2) . ?
N11 C11 1.3202(19) . ?
N11 C12 1.487(2) . ?
N21 C21 1.3318(19) . ?
N21 C22 1.478(2) . ?
O11 C11 1.3058(19) . ?
O21 C21 1.220(2) . ?
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 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C12 C15 1.529(3) . ?
C12 C13 1.530(2) . ?
C12 C14 1.534(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C22 C23 1.525(2) . ?
C22 C24 1.529(2) . ?
C22 C25 1.533(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
O11 Sn1 N21 90.11(5) . . ?
O11 Sn1 N11 59.15(4) . . ?
N21 Sn1 N11 94.47(5) . . ?
O11 Sn1 N2 76.27(4) . . ?
N21 Sn1 N2 57.90(5) . . ?
N11 Sn1 N2 127.90(4) . . ?
C11 N1 C2 119.15(15) . . ?
C11 N1 C1 118.19(15) . . ?
C2 N1 C1 114.17(16) . . ?
C3 N2 C4 110.06(14) . . ?
C3 N2 C21 108.33(14) . . ?
C4 N2 C21 112.07(14) . . ?
C3 N2 Sn1 112.60(11) . . ?
C4 N2 Sn1 124.32(12) . . ?
C21 N2 Sn1 86.42(8) . . ?
C11 N11 C12 128.58(13) . . ?
C11 N11 Sn1 89.35(9) . . ?
C12 N11 Sn1 133.40(10) . . ?
C21 N21 C22 121.09(13) . . ?
C21 N21 Sn1 104.19(10) . . ?
C22 N21 Sn1 133.17(9) . . ?
C11 O11 Sn1 96.33(9) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O11 C11 N11 115.16(13) . . ?
O11 C11 N1 116.99(14) . . ?
N11 C11 N1 127.84(14) . . ?
N11 C12 C15 105.27(13) . . ?
N11 C12 C13 114.53(13) . . ?
C15 C12 C13 107.13(16) . . ?
N11 C12 C14 112.02(15) . . ?
C15 C12 C14 108.04(17) . . ?
C13 C12 C14 109.46(15) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O21 C21 N21 131.57(16) . . ?
O21 C21 N2 121.00(14) . . ?
N21 C21 N2 107.42(13) . . ?
N21 C22 C23 110.41(13) . . ?
N21 C22 C24 106.28(13) . . ?
C23 C22 C24 110.45(15) . . ?
N21 C22 C25 110.86(13) . . ?
C23 C22 C25 110.83(15) . . ?
C24 C22 C25 107.89(15) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 952206'