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The mol­ecular structure of the title compound, [SnBr2(C9H12N)(C9H13N)][SnBr4(C9H12N)], consists of a dibromo­bis[2-(dimethyl­aminomethyl)phenyl][2-dimethylammoniomethyl)phenyl]tin(IV) cation and a tetra­bromo­[2-(dimethyl­aminomethyl)phenyl]tin(IV) anion. As a result of strong intra­molecular N→Sn inter­actions, distorted trigonal–bipy­ramidal and octa­hedral coordination geometries are established for the metal centres of the diorganotin(IV) and monoorganotin(IV) fragments, respectively. The cation and anion are linked together by two Br...H contacts, while three additional similar contacts result in a dimeric fragment which repeats in a two-dimensional supra­molecular arrangement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010605150X/av3053sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010605150X/av3053Isup2.hkl
Contains datablock I

CCDC reference: 638301

Comment top

During our work on organotin(IV) halides containing the [2-(Me2NCH2)C6H4] group (Varga et al., 2001, 2005, 2006), we isolated the title compound, (I), in which two ionic organotin(IV) fragments are present (Fig. 1). The structure is similar to that of the chloride derivative (Novak et al., 2006), but for the latter no intra- or intermolecular interactions were discussed.

The cationic fragment of compound (I) contains an Sn atom with a trigonal–bipyramidal coordination geometry, due to the strong intramolecular NSn interaction established by the N atom of the pendant arm from one organic ligand [Sn2—N2 = 2.421 (8) Å], while the other pendant arm is protonated at the N atom and is twisted away from the Sn centre. The anion has a hexacoordinated Sn, atom with the C atom of the ligand and the N atom from the intramolecularly coordinated NMe2 group [Sn1—N1 = 2.425 (6) Å] in cis positions.

Both the (C,N)CSnBr2 and (C,N)SnBr4 cores are distorted from ideal geometry as a consequence of the small `bite' of the pendant arm ligand [C10—Sn2—N2 = 75.5 (3)° and C1—Sn1—N1 = 78.4 (3)°]. The deviation of the metal atom (Sn2) from the equatorial plane (C10/C19/Br6) is 0.23 Å towards atom Br5 in the case of cation, while in the anion, atom C1 is 0.55 Å out of the best plane determined by Sn1/Br3/Br2/Br4, towards the pendant arm.

The intramolecular NSn interaction induces planar chirality at the metal centre (Varga et al., 2005, 2006) and the title compound crystallizes as a racemate, i.e. a mixture of SN2RN1 and RN2SN1 isomers.

The anion and cation of (I) are linked together by a hydrogen contact between one Br atom from the SN1-[{2-(Me2NCH2)C6H4}SnBr4]- anion and the H atom from the protonated pendant arm of the RN2-[{2-(Me2NCH2)C6H4}{2-(Me2NHCH2)C6H4}SnBr2]+ cation [Br4···H3Ai = 2.54 (5) Å; symmetry code: (i) 1 - x, 1 - y, -z]. Also, another hydrogen-bond type of interaction is formed between the RN2SN1 and SN2RN1 units [Br4···H26A = 3.116 Å], leading to a dimeric fragment (Fig. 2). This fragment is repeated in a two-dimensional supramolecular arrangement through the weak Br···H contacts [range 2.94–3.11 Å] (Fig. 3).

By contrast, a different supramolecular arrangement based on Cl···H contacts is observed for the chloride analogue (Novak et al., 2006). On the basis of the CIF file kindly provided by the Cambridge Crystallographic Data Centre, we found that in this case the anion and cation are connected through two Cl···H interactions (Cl1···H17B = 2.81 and Cl3···H17C = 2.82 Å), while three other interactions (Cl1···H12' = 2.78, Cl1···H16B = 2.98 and Cl4···H1' = 2.39 Å; symmetry code: (') -x, -y, 1 - z] lead to the formation of a dimeric structure. An interaction between the dimeric units (Cl2···H18C = 2.89 Å) connects them into a polymeric chain.

Related literature top

For related literature, see: Novak et al. (2006); Varga et al. (2001, 2005, 2006).

Experimental top

The title compound was obtained by the reaction between [{2-(Me2NCH2)C6H4}{2-(Me2NHCH2)C6H4}SnCl2]+[{2-(Me2NCH2)C6H4}SnC4]- and excess KBr in a CH2Cl2–H2O mixture (Ratio of solvents?). Crystals of (I) suitable for X-ray diffraction were obtained from a solution in a CH2Cl2n-hexane mixture (Ratio of solvents?).

Refinement top

All H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.93–0.97 Å [Please check added text], and with Uiso(H) = 1.5Ueq(C) for methyl H or 1.2Ueq(C) for aryl H atoms. The methyl groups were allowed to rotate but not to tip. Atom H3A bonded to N3 was calculated and fixed at the standard N—H distance of 0.87 (5) Å.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2006).

Figures top
[Figure 1] Fig. 1. : View of compound (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. : The hydrogen-bonding (dashed lines) in crystal structure of compound (I). [Symmetry code: (') 1 - x, 1 - y, - z; ('') 2 - x, 1 - y, 1 - z; (''') 1 - x, 1 - y, 1 - z; ('''') -1 + x, y, - 1 + z; (''''') x, y, -1 + z.]
[Figure 3] Fig. 3. : Supramolecular arrangement of (I). Hydrogen bonding shown with dashed lines.
dibromobis[2-(dimethylamino)methyl]tin(IV) tetrabromo[2-(dimethylamino)methyl]tin(IV) top
Crystal data top
[SnBr2(C9H12N)2][SnBr4(C9H12N)]F(000) = 2120
Mr = 1120.44Dx = 2.133 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4671 reflections
a = 9.5330 (5) Åθ = 2.2–22.7°
b = 36.635 (2) ŵ = 8.33 mm1
c = 10.0344 (6) ÅT = 297 K
β = 95.479 (1)°Block, colourless
V = 3488.4 (3) Å30.24 × 0.21 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6137 independent reflections
Radiation source: fine-focus sealed tube5141 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1111
Tmin = 0.141, Tmax = 0.368k = 4342
25246 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0501P)2 + 13.0613P]
where P = (Fo2 + 2Fc2)/3
6137 reflections(Δ/σ)max = 0.001
353 parametersΔρmax = 1.10 e Å3
1 restraintΔρmin = 0.98 e Å3
Crystal data top
[SnBr2(C9H12N)2][SnBr4(C9H12N)]V = 3488.4 (3) Å3
Mr = 1120.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.5330 (5) ŵ = 8.33 mm1
b = 36.635 (2) ÅT = 297 K
c = 10.0344 (6) Å0.24 × 0.21 × 0.12 mm
β = 95.479 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
6137 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
5141 reflections with I > 2σ(I)
Tmin = 0.141, Tmax = 0.368Rint = 0.048
25246 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0531 restraint
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0501P)2 + 13.0613P]
where P = (Fo2 + 2Fc2)/3
6137 reflectionsΔρmax = 1.10 e Å3
353 parametersΔρmin = 0.98 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.45399 (9)0.43640 (3)0.20347 (9)0.0497 (2)
Br20.72725 (11)0.49177 (3)0.06030 (9)0.0540 (3)
Br30.70387 (11)0.39449 (3)0.01387 (9)0.0581 (3)
Br40.74413 (9)0.47849 (2)0.42327 (8)0.0468 (2)
C10.7793 (9)0.3864 (2)0.3139 (8)0.0409 (19)
C20.9253 (10)0.3803 (3)0.3399 (10)0.058 (3)
C30.9685 (13)0.3463 (3)0.3881 (11)0.077 (3)
H31.06420.34110.40260.092*
C40.8705 (15)0.3202 (3)0.4150 (12)0.082 (4)
H40.90130.29770.44930.098*
C50.7335 (14)0.3266 (3)0.3927 (11)0.074 (3)
H50.66930.30860.41080.089*
C60.6856 (11)0.3598 (3)0.3427 (10)0.063 (3)
H60.58930.36430.32840.076*
C71.0245 (10)0.4133 (3)0.3300 (11)0.075 (3)
H7A1.02750.42730.41230.090*
H7B1.11910.40460.32050.090*
C81.0463 (11)0.4732 (3)0.2422 (13)0.082 (4)
H8A1.01190.48430.31940.124*
H8B1.02300.48830.16520.124*
H8C1.14680.47050.25670.124*
C91.0307 (11)0.4239 (4)0.0935 (11)0.079 (4)
H9A1.13160.42200.10430.119*
H9B1.00290.44100.02330.119*
H9C0.99050.40050.07090.119*
N10.9803 (7)0.43670 (19)0.2192 (7)0.0423 (16)
Sn10.72496 (5)0.434562 (14)0.20284 (5)0.03062 (15)
Br50.64191 (13)0.67775 (4)0.47850 (12)0.0798 (4)
Br60.86476 (12)0.73173 (3)0.25672 (14)0.0775 (4)
C100.5011 (8)0.6955 (2)0.1426 (10)0.045 (2)
C110.4985 (10)0.7084 (2)0.0144 (12)0.059 (3)
C120.3707 (11)0.7212 (3)0.0497 (13)0.073 (3)
H120.36850.73010.13670.088*
C130.2503 (12)0.7208 (3)0.0122 (16)0.084 (4)
H130.16560.72860.03220.101*
C140.2563 (11)0.7087 (3)0.1404 (15)0.079 (4)
H140.17490.70970.18450.095*
C150.3779 (10)0.6951 (2)0.2084 (12)0.062 (3)
H150.37800.68600.29490.074*
C160.6323 (10)0.7107 (3)0.0535 (11)0.059 (3)
H16A0.61060.70950.14980.071*
H16B0.67910.73370.03180.071*
C170.6689 (10)0.6456 (2)0.0668 (9)0.051 (2)
H17A0.66680.64690.16250.077*
H17B0.57500.64200.04220.077*
H17C0.72750.62560.03410.077*
C180.8708 (9)0.6860 (3)0.0465 (10)0.057 (2)
H18A0.86840.68660.14230.086*
H18B0.93070.66640.01230.086*
H18C0.90680.70870.01000.086*
C190.8353 (8)0.6317 (2)0.2496 (8)0.0387 (19)
C200.7922 (7)0.5944 (2)0.2438 (7)0.0317 (17)
C210.8938 (9)0.5675 (2)0.2645 (8)0.043 (2)
H210.86640.54320.25900.052*
C221.0337 (9)0.5757 (2)0.2929 (9)0.045 (2)
H221.09900.55700.30980.054*
C231.0770 (9)0.6106 (3)0.2963 (10)0.053 (2)
H231.17240.61610.31150.063*
C240.9785 (9)0.6383 (2)0.2772 (9)0.049 (2)
H241.00950.66240.28310.058*
C250.6412 (8)0.5834 (2)0.2101 (8)0.0383 (18)
H25A0.63110.57250.12160.046*
H25B0.58240.60510.20760.046*
C260.4527 (8)0.5405 (3)0.2609 (9)0.050 (2)
H26A0.38320.55940.24750.075*
H26B0.42500.52350.32620.075*
H26C0.46070.52800.17780.075*
C270.5888 (12)0.5725 (3)0.4452 (9)0.071 (3)
H27A0.57300.55350.50760.106*
H27B0.51480.59030.44510.106*
H27C0.67780.58400.47100.106*
H3A0.646 (6)0.5384 (13)0.327 (7)0.03 (2)*
N20.7261 (7)0.68006 (18)0.0076 (8)0.0477 (18)
N30.5902 (7)0.55679 (18)0.3088 (7)0.0373 (15)
Sn20.70216 (6)0.678224 (15)0.23036 (7)0.04434 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0368 (5)0.0539 (6)0.0579 (6)0.0008 (4)0.0027 (4)0.0052 (4)
Br20.0672 (6)0.0466 (5)0.0469 (5)0.0040 (4)0.0011 (4)0.0065 (4)
Br30.0668 (6)0.0589 (6)0.0479 (5)0.0018 (5)0.0018 (4)0.0090 (5)
Br40.0543 (5)0.0491 (5)0.0367 (5)0.0063 (4)0.0033 (4)0.0026 (4)
C10.043 (5)0.040 (5)0.039 (5)0.011 (4)0.001 (4)0.000 (4)
C20.056 (6)0.057 (6)0.060 (6)0.017 (5)0.005 (5)0.017 (5)
C30.078 (8)0.084 (8)0.067 (7)0.048 (7)0.002 (6)0.022 (6)
C40.120 (11)0.050 (7)0.073 (8)0.021 (7)0.006 (7)0.020 (6)
C50.088 (9)0.050 (7)0.082 (8)0.004 (6)0.004 (7)0.021 (6)
C60.067 (7)0.045 (6)0.075 (7)0.002 (5)0.006 (5)0.024 (5)
C70.044 (6)0.120 (10)0.061 (7)0.010 (6)0.003 (5)0.007 (7)
C80.044 (6)0.087 (9)0.115 (10)0.003 (6)0.002 (6)0.026 (7)
C90.051 (6)0.125 (11)0.066 (7)0.016 (6)0.020 (5)0.018 (7)
N10.033 (4)0.050 (4)0.045 (4)0.007 (3)0.011 (3)0.004 (3)
Sn10.0305 (3)0.0310 (3)0.0302 (3)0.0030 (2)0.0021 (2)0.0011 (2)
Br50.0741 (8)0.0919 (9)0.0768 (8)0.0123 (6)0.0244 (6)0.0130 (7)
Br60.0594 (6)0.0479 (6)0.1284 (11)0.0124 (5)0.0253 (6)0.0342 (6)
C100.032 (4)0.026 (4)0.078 (7)0.004 (3)0.012 (4)0.006 (4)
C110.046 (5)0.031 (5)0.101 (8)0.003 (4)0.010 (5)0.001 (5)
C120.058 (7)0.055 (6)0.104 (9)0.004 (5)0.007 (6)0.006 (6)
C130.044 (6)0.062 (7)0.145 (13)0.001 (5)0.001 (7)0.003 (8)
C140.038 (6)0.062 (7)0.140 (12)0.005 (5)0.022 (7)0.025 (8)
C150.046 (6)0.038 (5)0.104 (8)0.004 (4)0.021 (5)0.013 (5)
C160.056 (6)0.046 (6)0.079 (7)0.008 (4)0.017 (5)0.020 (5)
C170.061 (6)0.036 (5)0.058 (6)0.001 (4)0.015 (5)0.000 (4)
C180.046 (5)0.055 (6)0.074 (7)0.004 (4)0.020 (5)0.009 (5)
C190.032 (4)0.039 (5)0.048 (5)0.004 (3)0.017 (4)0.002 (4)
C200.029 (4)0.039 (4)0.026 (4)0.000 (3)0.000 (3)0.001 (3)
C210.046 (5)0.036 (5)0.048 (5)0.001 (4)0.003 (4)0.000 (4)
C220.037 (5)0.044 (5)0.054 (5)0.008 (4)0.007 (4)0.001 (4)
C230.028 (4)0.061 (6)0.070 (6)0.003 (4)0.005 (4)0.008 (5)
C240.044 (5)0.036 (5)0.067 (6)0.005 (4)0.012 (4)0.008 (4)
C250.045 (5)0.031 (4)0.038 (4)0.007 (4)0.000 (4)0.004 (3)
C260.038 (5)0.053 (6)0.059 (6)0.013 (4)0.006 (4)0.006 (5)
C270.077 (7)0.095 (8)0.042 (5)0.022 (6)0.015 (5)0.016 (5)
N20.043 (4)0.031 (4)0.072 (5)0.001 (3)0.018 (4)0.004 (4)
N30.033 (4)0.038 (4)0.041 (4)0.002 (3)0.003 (3)0.007 (3)
Sn20.0339 (3)0.0310 (3)0.0699 (4)0.0004 (2)0.0141 (3)0.0094 (3)
Geometric parameters (Å, º) top
Br1—Sn12.5847 (10)C13—C141.356 (18)
Br2—Sn12.5386 (10)C13—H130.9300
Br3—Sn12.6154 (10)C14—C151.380 (15)
Br4—Sn12.7274 (10)C14—H140.9300
Br5—Sn22.6083 (14)C15—H150.9300
Br6—Sn22.4975 (11)C16—N21.481 (11)
N1—Sn12.425 (6)C16—H16A0.9700
N2—Sn22.421 (8)C16—H16B0.9700
C1—Sn12.125 (8)C17—N21.476 (11)
C10—Sn22.128 (8)C17—H17A0.9600
C19—Sn22.123 (8)C17—H17B0.9600
C1—C61.369 (12)C17—H17C0.9600
C1—C21.409 (12)C18—N21.484 (10)
C2—C31.384 (13)C18—H18A0.9600
C2—C71.545 (15)C18—H18B0.9600
C3—C41.382 (17)C18—H18C0.9600
C3—H30.9300C19—C241.388 (11)
C4—C51.325 (16)C19—C201.425 (11)
C4—H40.9300C20—C211.384 (11)
C5—C61.378 (13)C20—C251.502 (10)
C5—H50.9300C21—C221.370 (11)
C6—H60.9300C21—H210.9300
C7—N11.434 (12)C22—C231.343 (12)
C7—H7A0.9700C22—H220.9300
C7—H7B0.9700C23—C241.383 (12)
C8—N11.486 (12)C23—H230.9300
C8—H8A0.9600C24—H240.9300
C8—H8B0.9600C25—N31.503 (10)
C8—H8C0.9600C25—H25A0.9700
C9—N11.468 (11)C25—H25B0.9700
C9—H9A0.9600C26—N31.478 (10)
C9—H9B0.9600C26—H26A0.9600
C9—H9C0.9600C26—H26B0.9600
C10—C111.368 (14)C26—H26C0.9600
C10—C151.401 (12)C27—N31.487 (11)
C11—C121.403 (14)C27—H27A0.9600
C11—C161.505 (13)C27—H27B0.9600
C12—C131.357 (16)C27—H27C0.9600
C12—H120.9300N3—H3A0.86 (2)
C6—C1—C2120.1 (8)N2—C16—H16A109.8
C6—C1—Sn1124.7 (6)C11—C16—H16A109.8
C2—C1—Sn1114.5 (6)N2—C16—H16B109.8
C3—C2—C1117.6 (10)C11—C16—H16B109.8
C3—C2—C7124.3 (10)H16A—C16—H16B108.3
C1—C2—C7117.7 (8)N2—C17—H17A109.5
C4—C3—C2120.5 (10)N2—C17—H17B109.5
C4—C3—H3119.8H17A—C17—H17B109.5
C2—C3—H3119.8N2—C17—H17C109.5
C5—C4—C3121.2 (10)H17A—C17—H17C109.5
C5—C4—H4119.4H17B—C17—H17C109.5
C3—C4—H4119.4N2—C18—H18A109.5
C4—C5—C6120.4 (11)N2—C18—H18B109.5
C4—C5—H5119.8H18A—C18—H18B109.5
C6—C5—H5119.8N2—C18—H18C109.5
C1—C6—C5120.3 (10)H18A—C18—H18C109.5
C1—C6—H6119.9H18B—C18—H18C109.5
C5—C6—H6119.9C24—C19—C20116.7 (7)
N1—C7—C2112.4 (8)C24—C19—Sn2116.5 (6)
N1—C7—H7A109.1C20—C19—Sn2126.7 (5)
C2—C7—H7A109.1C21—C20—C19118.7 (7)
N1—C7—H7B109.1C21—C20—C25119.0 (7)
C2—C7—H7B109.1C19—C20—C25122.2 (7)
H7A—C7—H7B107.9C22—C21—C20122.0 (8)
N1—C8—H8A109.5C22—C21—H21119.0
N1—C8—H8B109.5C20—C21—H21119.0
H8A—C8—H8B109.5C23—C22—C21120.3 (8)
N1—C8—H8C109.5C23—C22—H22119.9
H8A—C8—H8C109.5C21—C22—H22119.9
H8B—C8—H8C109.5C22—C23—C24119.5 (8)
N1—C9—H9A109.5C22—C23—H23120.3
N1—C9—H9B109.5C24—C23—H23120.3
H9A—C9—H9B109.5C23—C24—C19122.8 (8)
N1—C9—H9C109.5C23—C24—H24118.6
H9A—C9—H9C109.5C19—C24—H24118.6
H9B—C9—H9C109.5C20—C25—N3112.9 (6)
C7—N1—C9112.3 (8)C20—C25—H25A109.0
C7—N1—C8109.1 (8)N3—C25—H25A109.0
C9—N1—C8104.5 (8)C20—C25—H25B109.0
C7—N1—Sn1104.6 (5)N3—C25—H25B109.0
C9—N1—Sn1109.9 (6)H25A—C25—H25B107.8
C8—N1—Sn1116.6 (5)N3—C26—H26A109.5
C1—Sn1—N178.4 (3)N3—C26—H26B109.5
C1—Sn1—Br2165.1 (2)H26A—C26—H26B109.5
N1—Sn1—Br287.07 (17)N3—C26—H26C109.5
C1—Sn1—Br1102.3 (2)H26A—C26—H26C109.5
N1—Sn1—Br1174.79 (16)H26B—C26—H26C109.5
Br2—Sn1—Br192.42 (4)N3—C27—H27A109.5
C1—Sn1—Br388.0 (2)N3—C27—H27B109.5
N1—Sn1—Br394.09 (16)H27A—C27—H27B109.5
Br2—Sn1—Br389.94 (4)N3—C27—H27C109.5
Br1—Sn1—Br391.10 (3)H27A—C27—H27C109.5
C1—Sn1—Br494.1 (2)H27B—C27—H27C109.5
N1—Sn1—Br486.39 (16)C17—N2—C16109.5 (7)
Br2—Sn1—Br488.07 (3)C17—N2—C18109.6 (7)
Br1—Sn1—Br488.41 (3)C16—N2—C18110.9 (7)
Br3—Sn1—Br4177.93 (4)C17—N2—Sn2107.9 (5)
C11—C10—C15120.4 (9)C16—N2—Sn2102.5 (5)
C11—C10—Sn2115.2 (6)C18—N2—Sn2116.1 (6)
C15—C10—Sn2124.4 (8)C26—N3—C27111.7 (7)
C10—C11—C12118.9 (10)C26—N3—C25112.4 (6)
C10—C11—C16120.3 (9)C27—N3—C25112.7 (7)
C12—C11—C16120.6 (10)C26—N3—H3A105 (5)
C13—C12—C11121.5 (12)C27—N3—H3A100 (5)
C13—C12—H12119.3C25—N3—H3A114 (5)
C11—C12—H12119.3C19—Sn2—C10141.6 (3)
C14—C13—C12118.5 (11)C19—Sn2—N290.0 (3)
C14—C13—H13120.8C10—Sn2—N275.5 (3)
C12—C13—H13120.8C19—Sn2—Br6105.1 (2)
C13—C14—C15122.9 (11)C10—Sn2—Br6109.6 (2)
C13—C14—H14118.5N2—Sn2—Br688.09 (17)
C15—C14—H14118.5C19—Sn2—Br595.3 (2)
C14—C15—C10117.8 (11)C10—Sn2—Br597.2 (3)
C14—C15—H15121.1N2—Sn2—Br5172.63 (17)
C10—C15—H15121.1Br6—Sn2—Br595.46 (5)
N2—C16—C11109.2 (7)
C6—C1—C2—C33.3 (14)C11—C10—C15—C141.3 (13)
Sn1—C1—C2—C3167.7 (8)Sn2—C10—C15—C14177.2 (7)
C6—C1—C2—C7169.1 (9)C10—C11—C16—N234.0 (12)
Sn1—C1—C2—C720.0 (11)C12—C11—C16—N2149.5 (9)
C1—C2—C3—C42.8 (16)C24—C19—C20—C210.5 (11)
C7—C2—C3—C4168.9 (11)Sn2—C19—C20—C21177.1 (6)
C2—C3—C4—C51.5 (19)C24—C19—C20—C25177.8 (7)
C3—C4—C5—C60.4 (19)Sn2—C19—C20—C255.5 (11)
C2—C1—C6—C52.3 (15)C19—C20—C21—C221.3 (12)
Sn1—C1—C6—C5167.6 (8)C25—C20—C21—C22178.7 (7)
C4—C5—C6—C10.9 (18)C20—C21—C22—C232.6 (13)
C3—C2—C7—N1148.2 (10)C21—C22—C23—C243.0 (14)
C1—C2—C7—N140.1 (13)C22—C23—C24—C192.3 (14)
C2—C7—N1—C984.2 (10)C20—C19—C24—C231.0 (13)
C2—C7—N1—C8160.3 (8)Sn2—C19—C24—C23178.0 (7)
C2—C7—N1—Sn134.9 (9)C21—C20—C25—N353.1 (10)
C6—C1—Sn1—N1170.3 (8)C19—C20—C25—N3129.6 (7)
C2—C1—Sn1—N10.2 (6)C11—C16—N2—C1772.1 (10)
C6—C1—Sn1—Br2157.9 (7)C11—C16—N2—C18166.8 (8)
C2—C1—Sn1—Br212.5 (13)C11—C16—N2—Sn242.2 (9)
C6—C1—Sn1—Br115.0 (8)C20—C25—N3—C26168.4 (7)
C2—C1—Sn1—Br1174.5 (6)C20—C25—N3—C2764.3 (9)
C6—C1—Sn1—Br375.7 (8)C24—C19—Sn2—C10156.8 (6)
C2—C1—Sn1—Br394.8 (6)C20—C19—Sn2—C1026.6 (10)
C6—C1—Sn1—Br4104.3 (8)C24—C19—Sn2—N290.5 (6)
C2—C1—Sn1—Br485.3 (6)C20—C19—Sn2—N292.8 (7)
C7—N1—Sn1—C120.1 (6)C24—C19—Sn2—Br62.5 (7)
C9—N1—Sn1—C1100.7 (7)C20—C19—Sn2—Br6179.1 (6)
C8—N1—Sn1—C1140.6 (7)C24—C19—Sn2—Br594.6 (6)
C7—N1—Sn1—Br2163.1 (6)C20—C19—Sn2—Br582.0 (7)
C9—N1—Sn1—Br276.2 (7)C11—C10—Sn2—C1988.5 (8)
C8—N1—Sn1—Br242.5 (7)C15—C10—Sn2—C1993.0 (8)
C7—N1—Sn1—Br3107.2 (6)C11—C10—Sn2—N217.5 (6)
C9—N1—Sn1—Br313.6 (7)C15—C10—Sn2—N2164.0 (8)
C8—N1—Sn1—Br3132.2 (7)C11—C10—Sn2—Br665.1 (7)
C7—N1—Sn1—Br474.8 (6)C15—C10—Sn2—Br6113.4 (7)
C9—N1—Sn1—Br4164.4 (7)C11—C10—Sn2—Br5163.6 (6)
C8—N1—Sn1—Br445.7 (7)C15—C10—Sn2—Br514.9 (7)
C15—C10—C11—C120.1 (13)C17—N2—Sn2—C1082.6 (5)
Sn2—C10—C11—C12178.5 (7)C16—N2—Sn2—C1032.9 (5)
C15—C10—C11—C16176.6 (8)C18—N2—Sn2—C10154.0 (6)
Sn2—C10—C11—C161.9 (11)C17—N2—Sn2—Br6166.6 (5)
C10—C11—C12—C130.5 (16)C16—N2—Sn2—Br677.9 (5)
C16—C11—C12—C13177.0 (10)C18—N2—Sn2—Br643.2 (5)
C11—C12—C13—C142.0 (18)C17—N2—Sn2—Br574.5 (14)
C12—C13—C14—C153.3 (18)C16—N2—Sn2—Br541.0 (16)
C13—C14—C15—C102.9 (16)C18—N2—Sn2—Br5162.1 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Br40.86 (5)2.54 (5)3.373 (7)161 (5)
C21—H21···Br20.932.963.714 (7)139
C26—H26C···Br2i0.962.943.698 (9)137
C26—H26A···Br3i0.962.943.652 (10)132
C17—H17B···Br3i0.963.073.999 (10)162
C3—H3···Br5ii0.933.023.926 (12)166
C26—H26B···Br4iii0.963.113.897 (9)140
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[SnBr2(C9H12N)2][SnBr4(C9H12N)]
Mr1120.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)297
a, b, c (Å)9.5330 (5), 36.635 (2), 10.0344 (6)
β (°) 95.479 (1)
V3)3488.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)8.33
Crystal size (mm)0.24 × 0.21 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.141, 0.368
No. of measured, independent and
observed [I > 2σ(I)] reflections
25246, 6137, 5141
Rint0.048
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.122, 1.11
No. of reflections6137
No. of parameters353
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0501P)2 + 13.0613P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.10, 0.98

Computer programs: SMART (Bruker, 2000), SMART, SAINT-Plus (Bruker, 2000), SHELXTL (Bruker, 2001), SHELXTL, ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2006).

Selected geometric parameters (Å, º) top
Br1—Sn12.5847 (10)N1—Sn12.425 (6)
Br2—Sn12.5386 (10)N2—Sn22.421 (8)
Br3—Sn12.6154 (10)C1—Sn12.125 (8)
Br4—Sn12.7274 (10)C10—Sn22.128 (8)
Br5—Sn22.6083 (14)C19—Sn22.123 (8)
Br6—Sn22.4975 (11)
C1—Sn1—N178.4 (3)Br1—Sn1—Br488.41 (3)
C1—Sn1—Br2165.1 (2)Br3—Sn1—Br4177.93 (4)
N1—Sn1—Br287.07 (17)C19—Sn2—C10141.6 (3)
C1—Sn1—Br1102.3 (2)C19—Sn2—N290.0 (3)
N1—Sn1—Br1174.79 (16)C10—Sn2—N275.5 (3)
Br2—Sn1—Br192.42 (4)C19—Sn2—Br6105.1 (2)
C1—Sn1—Br388.0 (2)C10—Sn2—Br6109.6 (2)
N1—Sn1—Br394.09 (16)N2—Sn2—Br688.09 (17)
Br2—Sn1—Br389.94 (4)C19—Sn2—Br595.3 (2)
Br1—Sn1—Br391.10 (3)C10—Sn2—Br597.2 (3)
C1—Sn1—Br494.1 (2)N2—Sn2—Br5172.63 (17)
N1—Sn1—Br486.39 (16)Br6—Sn2—Br595.46 (5)
Br2—Sn1—Br488.07 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Br40.86 (5)2.54 (5)3.373 (7)161 (5)
C21—H21···Br20.932.963.714 (7)139
C26—H26C···Br2i0.962.943.698 (9)137
C26—H26A···Br3i0.962.943.652 (10)132
C17—H17B···Br3i0.963.073.999 (10)162
C3—H3···Br5ii0.933.023.926 (12)166
C26—H26B···Br4iii0.963.113.897 (9)140
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+1.
 

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