μ-Hydroxo-bis­{[2-(dimethyl­amino­meth­yl)­phen­yl]dimethyl­tin(IV)} iodide

The cation of the title compound, [Sn₂(CH₃)₄(OH)(C₉H₁₂N)₂]I, consists of two [2-(Me₂NCH₂)C₆H₄]SnMe₂ units bridged by a hydr­oxy group, located on a twofold rotation axis. Both Sn atoms are penta­coordinated in a distorted trigonal–bipyramidal coordination geometry as the result of a strong intra­molecular N→Sn inter­action trans to the Sn—O bond [N—Sn—O = 168.70 (7)°]. The iodide ion also lies on a twofold rotation axis.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C)= 0.005 Å
• R factor = 0.025
• wR factor = 0.060
• Data-to-parameter ratio = 20.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; 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, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

µ-Hydroxo-bis{2-(dimethylaminomethyl)phenyl]dimethyltin(IV)} iodide

Crystal data

[Sn2(CH3)4(OH)(C9H12N)2]I	F(000) = 1376
Mr = 709.86	Dx = 1.791 Mg m^−3
Monoclinic, C2/c	Melting point: 106 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 9.4994 (14) Å	Cell parameters from 5156 reflections
b = 18.762 (3) Å	θ = 2.4–27.5°
c = 14.778 (2) Å	µ = 3.09 mm^−1
β = 92.240 (2)°	T = 297 K
V = 2631.8 (7) Å^3	Block, colourless
Z = 4	0.42 × 0.35 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2697 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.293, Tmax = 0.537	k = −23→23
10450 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0274P)^2 + 2.4944P] where P = (Fo^2 + 2Fc^2)/3
2697 reflections	(Δ/σ)max = 0.002
134 parameters	Δρmax = 0.51 e Å^−3
1 restraint	Δρmin = −0.61 e Å^−3

Special details

Experimental. Bruker(2000).SADABS+. Version 2.03, Bruker AXS Inc., Madison, Wisconsin, USA.

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 (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.17039 (2)	0.348767 (10)	0.675117 (13)	0.03611 (8)
N1	0.3372 (3)	0.39061 (16)	0.56249 (19)	0.0513 (7)
O1	0.0000	0.30677 (16)	0.7500	0.0423 (7)
H1	0.0000	0.2638 (11)	0.7500	0.043 (13)*
I1	0.5000	0.616037 (17)	0.7500	0.05580 (11)
C1	0.0463 (3)	0.35862 (16)	0.5529 (2)	0.0392 (7)
C2	0.1062 (4)	0.39831 (18)	0.4846 (2)	0.0502 (8)
C3	0.0310 (5)	0.4073 (2)	0.4022 (3)	0.0696 (11)
H3	0.0714	0.4326	0.3557	0.083*
C4	−0.1013 (5)	0.3793 (2)	0.3891 (3)	0.0695 (11)
H4	−0.1500	0.3855	0.3338	0.083*
C5	−0.1622 (4)	0.3420 (2)	0.4569 (3)	0.0638 (11)
H5	−0.2529	0.3240	0.4483	0.077*
C6	−0.0884 (4)	0.33129 (18)	0.5385 (2)	0.0499 (8)
H6	−0.1296	0.3055	0.5842	0.060*
C7	0.2478 (4)	0.4338 (2)	0.5027 (3)	0.0613 (9)
H7A	0.2936	0.4410	0.4459	0.074*
H7B	0.2339	0.4801	0.5301	0.074*
C8	0.3896 (5)	0.3277 (2)	0.5109 (3)	0.0703 (11)
H8A	0.3109	0.3004	0.4875	0.105*
H8B	0.4474	0.2984	0.5506	0.105*
H8C	0.4441	0.3441	0.4616	0.105*
C9	0.4607 (4)	0.4290 (3)	0.5987 (3)	0.0778 (13)
H9A	0.5257	0.4362	0.5514	0.117*
H9B	0.5055	0.4016	0.6466	0.117*
H9C	0.4322	0.4743	0.6219	0.117*
C10	0.1933 (4)	0.44260 (18)	0.7554 (2)	0.0536 (8)
H10A	0.1410	0.4808	0.7270	0.080*
H10B	0.2911	0.4554	0.7611	0.080*
H10C	0.1582	0.4339	0.8144	0.080*
C11	0.3035 (3)	0.2622 (2)	0.7125 (3)	0.0581 (9)
H11A	0.2747	0.2206	0.6788	0.087*
H11B	0.2971	0.2530	0.7761	0.087*
H11C	0.3990	0.2739	0.6995	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.03701 (13)	0.03570 (12)	0.03577 (12)	−0.00249 (8)	0.00340 (8)	−0.00279 (8)
N1	0.0499 (16)	0.0547 (17)	0.0500 (16)	−0.0190 (13)	0.0107 (13)	−0.0042 (13)
O1	0.0472 (17)	0.0331 (16)	0.0476 (17)	0.000	0.0155 (13)	0.000
I1	0.0623 (2)	0.04385 (18)	0.0615 (2)	0.000	0.00545 (16)	0.000
C1	0.0432 (17)	0.0367 (15)	0.0379 (15)	−0.0008 (12)	0.0027 (13)	−0.0044 (12)
C2	0.059 (2)	0.0452 (18)	0.0470 (18)	−0.0039 (15)	0.0036 (15)	0.0068 (15)
C3	0.093 (3)	0.064 (2)	0.051 (2)	−0.008 (2)	−0.007 (2)	0.0210 (19)
C4	0.091 (3)	0.059 (2)	0.056 (2)	0.002 (2)	−0.027 (2)	0.0053 (19)
C5	0.062 (2)	0.059 (2)	0.068 (3)	−0.0044 (18)	−0.020 (2)	−0.0082 (19)
C6	0.0483 (19)	0.0497 (19)	0.0514 (19)	−0.0065 (15)	−0.0002 (15)	−0.0038 (15)
C7	0.068 (2)	0.053 (2)	0.063 (2)	−0.0145 (18)	0.0119 (18)	0.0114 (17)
C8	0.071 (3)	0.073 (3)	0.068 (3)	−0.008 (2)	0.030 (2)	−0.011 (2)
C9	0.062 (2)	0.086 (3)	0.086 (3)	−0.034 (2)	0.008 (2)	0.002 (2)
C10	0.059 (2)	0.0478 (19)	0.054 (2)	−0.0081 (16)	0.0045 (16)	−0.0116 (16)
C11	0.0427 (19)	0.057 (2)	0.075 (2)	0.0069 (16)	0.0017 (17)	0.0083 (18)

Geometric parameters (Å, º)

Sn1—C1	2.126 (3)	C5—C6	1.386 (5)
Sn1—C10	2.130 (3)	C5—H5	0.9300
Sn1—C11	2.118 (3)	C6—H6	0.9300
O1—Sn1^i	2.1459 (11)	C7—H7A	0.9700
Sn1—O1	2.1459 (11)	C7—H7B	0.9700
Sn1—N1	2.470 (3)	C8—H8A	0.9600
N1—C7	1.449 (5)	C8—H8B	0.9600
N1—C9	1.460 (5)	C8—H8C	0.9600
N1—C8	1.501 (5)	C9—H9A	0.9600
O1—H1	0.807 (19)	C9—H9B	0.9600
C1—C6	1.386 (4)	C9—H9C	0.9600
C1—C2	1.393 (4)	C10—H10A	0.9600
C2—C3	1.398 (5)	C10—H10B	0.9600
C2—C7	1.516 (5)	C10—H10C	0.9600
C3—C4	1.369 (6)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.369 (6)	C11—H11C	0.9600
C4—H4	0.9300
C11—Sn1—C1	126.43 (14)	C5—C6—C1	120.8 (3)
C11—Sn1—C10	116.19 (15)	C5—C6—H6	119.6
C1—Sn1—C10	116.29 (13)	C1—C6—H6	119.6
C11—Sn1—O1	92.22 (12)	N1—C7—C2	110.9 (3)
C1—Sn1—O1	93.76 (8)	N1—C7—H7A	109.5
C10—Sn1—O1	94.52 (11)	C2—C7—H7A	109.5
C11—Sn1—N1	91.56 (12)	N1—C7—H7B	109.5
C1—Sn1—N1	75.46 (11)	C2—C7—H7B	109.5
C10—Sn1—N1	93.36 (12)	H7A—C7—H7B	108.1
O1—Sn1—N1	168.70 (7)	N1—C8—H8A	109.5
C7—N1—C9	113.0 (3)	N1—C8—H8B	109.5
C7—N1—C8	109.2 (3)	H8A—C8—H8B	109.5
C9—N1—C8	107.2 (3)	N1—C8—H8C	109.5
C7—N1—Sn1	102.3 (2)	H8A—C8—H8C	109.5
C9—N1—Sn1	115.9 (2)	H8B—C8—H8C	109.5
C8—N1—Sn1	109.1 (2)	N1—C9—H9A	109.5
Sn1—O1—Sn1^i	136.92 (15)	N1—C9—H9B	109.5
Sn1—O1—H1	111.54 (7)	H9A—C9—H9B	109.5
Sn1^i—O1—H1	111.54 (7)	N1—C9—H9C	109.5
C6—C1—C2	119.2 (3)	H9A—C9—H9C	109.5
C6—C1—Sn1	125.1 (2)	H9B—C9—H9C	109.5
C2—C1—Sn1	115.7 (2)	Sn1—C10—H10A	109.5
C1—C2—C3	119.1 (3)	Sn1—C10—H10B	109.5
C1—C2—C7	119.5 (3)	H10A—C10—H10B	109.5
C3—C2—C7	121.4 (3)	Sn1—C10—H10C	109.5
C4—C3—C2	120.8 (4)	H10A—C10—H10C	109.5
C4—C3—H3	119.6	H10B—C10—H10C	109.5
C2—C3—H3	119.6	Sn1—C11—H11A	109.5
C5—C4—C3	120.3 (4)	Sn1—C11—H11B	109.5
C5—C4—H4	119.9	H11A—C11—H11B	109.5
C3—C4—H4	119.9	Sn1—C11—H11C	109.5
C4—C5—C6	119.9 (4)	H11A—C11—H11C	109.5
C4—C5—H5	120.1	H11B—C11—H11C	109.5
C6—C5—H5	120.1
C11—Sn1—N1—C7	159.0 (2)	C11—Sn1—C1—C2	−96.7 (3)
C1—Sn1—N1—C7	31.6 (2)	C10—Sn1—C1—C2	70.8 (3)
C10—Sn1—N1—C7	−84.7 (2)	O1—Sn1—C1—C2	167.7 (2)
O1—Sn1—N1—C7	49.5 (6)	N1—Sn1—C1—C2	−15.7 (2)
C11—Sn1—N1—C9	−77.6 (3)	C6—C1—C2—C3	−2.4 (5)
C1—Sn1—N1—C9	155.0 (3)	Sn1—C1—C2—C3	−179.9 (3)
C10—Sn1—N1—C9	38.7 (3)	C6—C1—C2—C7	174.6 (3)
O1—Sn1—N1—C9	172.9 (5)	Sn1—C1—C2—C7	−3.0 (4)
C11—Sn1—N1—C8	43.4 (3)	C1—C2—C3—C4	1.8 (6)
C1—Sn1—N1—C8	−83.9 (3)	C7—C2—C3—C4	−175.2 (4)
C10—Sn1—N1—C8	159.8 (3)	C2—C3—C4—C5	0.2 (7)
O1—Sn1—N1—C8	−66.1 (6)	C3—C4—C5—C6	−1.5 (6)
C11—Sn1—O1—Sn1^i	147.14 (11)	C4—C5—C6—C1	0.8 (6)
C1—Sn1—O1—Sn1^i	−86.12 (8)	C2—C1—C6—C5	1.1 (5)
C10—Sn1—O1—Sn1^i	30.65 (10)	Sn1—C1—C6—C5	178.4 (3)
N1—Sn1—O1—Sn1^i	−103.4 (5)	C9—N1—C7—C2	−166.8 (3)
C11—Sn1—C1—C6	85.9 (3)	C8—N1—C7—C2	74.0 (4)
C10—Sn1—C1—C6	−106.6 (3)	Sn1—N1—C7—C2	−41.4 (3)
O1—Sn1—C1—C6	−9.7 (3)	C1—C2—C7—N1	34.6 (5)
N1—Sn1—C1—C6	166.9 (3)	C3—C2—C7—N1	−148.5 (4)

Symmetry code: (i) −x, y, −z+3/2.