{2,6-Bis­[(di­methyl­amino)­methyl]­phenyl-N²,C¹,N⁶}di­phenyl­tin(II) bromide monohydrate

In the title compound, [Sn(C₆H₅)₂(C₁₂H₁₉N₂)]Br·H₂O, the Sn^IV atom lies on a twofold axis and is coordinated by a C and two N atoms from the 2,6-bis­[(di­methyl­amino)­methyl]­phenyl ligand in a tridentate fashion and by two phenyl groups. The resulting geometry is intermediate between square pyramidal and trigonal bipyramidal, with three C atoms in equatorial and the two N atoms in axial positions. The main deformation from ideal trigonal-bipyramidal geometry is seen for the N-Sn-N angle [152.18 (7)°]. The Br^- anion and the water solvate mol­ecule are on an inversion centre and twofold axis, respectively. They form an infinite chain of Br...H-O-H...Br hydrogen bonds [Br...O 3.529 (2) Å] without contributing to the primary coordination sphere of the Sn atom.

Computing details

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and PLATON.

[1,6-bis(dimethylamino)methyl]phenyl}diphenyltin bromine monohydrate

Crystal data

[Sn(C6H5)2(C12H19N2)]Br·H2O	F(000) = 1128
Mr = 562.11	Dx = 1.566 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.8520 (3) Å	Cell parameters from 15656 reflections
b = 20.0760 (4) Å	θ = 1.0–27.5°
c = 10.4740 (2) Å	µ = 2.77 mm^−1
β = 125.0660 (12)°	T = 150 K
V = 2384.05 (8) Å^3	Prism, colorless
Z = 4	0.2 × 0.2 × 0.1 mm

Data collection

Nonius KappaCCD area detector diffractometer	2688 independent reflections
Radiation source: fine-focus sealed tube	2612 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
φ and ω scans to fill the Ewald sphere	h = −17→17
Absorption correction: empirical (using intensity measurements) (SORTAV; Blessing 1997)	k = −25→26
Tmin = 0.521, Tmax = 0.659	l = −13→13
23135 measured reflections

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)] = 0.020	Hydrogen site location: difference Fourier map
wR(F^2) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0239P)^2 + 2.3842P] where P = (Fo^2 + 2Fc^2)/3
2688 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.80 e Å^−3

Special details

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. Four strong reflections 020, 110, -111, 021 were omitted from the final refinement due inaccuracy in measurement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.0000	0.366077 (7)	0.7500	0.01590 (6)
Br1	0.2500	0.2500	0.5000	0.04973 (11)
N1	−0.07421 (12)	0.33686 (7)	0.48226 (16)	0.0212 (3)
C1	0.0000	0.26184 (11)	0.7500	0.0189 (4)
C2	−0.01541 (14)	0.22839 (8)	0.6222 (2)	0.0229 (3)
C3	−0.01502 (16)	0.15877 (9)	0.6233 (3)	0.0341 (4)
H3	−0.0247	0.1352	0.5402	0.037 (7)*
C4	0.0000	0.12493 (13)	0.7500	0.0383 (7)
H4	0.0000	0.0786	0.7500	0.036 (8)*
C5	−0.02655 (16)	0.26894 (9)	0.4920 (2)	0.0265 (4)
H51	0.0503	0.2728	0.5103	0.031 (6)*
H52	−0.0785	0.2460	0.3935	0.027 (5)*
C6	−0.20579 (14)	0.33304 (10)	0.3919 (2)	0.0259 (4)
H61	−0.2272	0.3045	0.4455	0.031 (6)*
H62	−0.2374	0.3153	0.2900	0.036 (6)*
H63	−0.2372	0.3768	0.3823	0.036 (6)*
C7	−0.04388 (18)	0.38221 (12)	0.3978 (2)	0.0345 (4)
H71	−0.0741	0.4259	0.3922	0.039 (6)*
H72	−0.0782	0.3656	0.2942	0.044 (7)*
H73	0.0403	0.3843	0.4525	0.036 (6)*
C8	0.14644 (14)	0.42717 (8)	0.80708 (19)	0.0195 (3)
C9	0.16362 (16)	0.48699 (9)	0.8871 (2)	0.0257 (4)
H9	0.1115	0.4989	0.9121	0.039 (6)*
C10	0.25819 (17)	0.52875 (9)	0.9294 (2)	0.0328 (4)
H10	0.2692	0.5681	0.9832	0.046 (7)*
C11	0.33563 (16)	0.51152 (10)	0.8913 (2)	0.0347 (5)
H11	0.3980	0.5397	0.9186	0.043 (7)*
C12	0.32062 (16)	0.45246 (11)	0.8127 (2)	0.0320 (4)
H12	0.3729	0.4411	0.7875	0.045 (7)*
C13	0.22657 (15)	0.41005 (9)	0.7713 (2)	0.0240 (3)
H13	0.2172	0.3703	0.7198	0.035 (6)*
O1	0.0000	0.15005 (14)	0.2500	0.0595 (7)
H1	0.055 (3)	0.1741 (15)	0.306 (4)	0.060 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01443 (9)	0.01512 (9)	0.01957 (9)	0.000	0.01059 (7)	0.000
Br1	0.02538 (16)	0.0933 (3)	0.03608 (18)	0.01450 (15)	0.02093 (14)	0.01933 (16)
N1	0.0162 (6)	0.0290 (7)	0.0186 (7)	−0.0008 (5)	0.0102 (6)	0.0000 (5)
C1	0.0146 (10)	0.0159 (10)	0.0259 (12)	0.000	0.0114 (9)	0.000
C2	0.0134 (7)	0.0232 (8)	0.0291 (9)	0.0003 (6)	0.0104 (7)	−0.0061 (7)
C3	0.0194 (8)	0.0248 (9)	0.0494 (12)	−0.0002 (7)	0.0147 (8)	−0.0134 (8)
C4	0.0218 (13)	0.0173 (12)	0.064 (2)	0.000	0.0178 (14)	0.000
C5	0.0211 (8)	0.0355 (10)	0.0249 (9)	0.0014 (7)	0.0144 (7)	−0.0084 (7)
C6	0.0159 (8)	0.0359 (10)	0.0224 (8)	−0.0009 (7)	0.0089 (7)	−0.0030 (7)
C7	0.0298 (10)	0.0521 (12)	0.0226 (9)	−0.0063 (9)	0.0156 (8)	0.0058 (8)
C8	0.0157 (7)	0.0199 (7)	0.0205 (7)	−0.0025 (6)	0.0089 (6)	0.0025 (6)
C9	0.0251 (9)	0.0229 (8)	0.0278 (9)	−0.0015 (7)	0.0145 (7)	−0.0001 (7)
C10	0.0321 (10)	0.0238 (9)	0.0292 (10)	−0.0082 (7)	0.0098 (8)	0.0004 (7)
C11	0.0210 (9)	0.0373 (10)	0.0305 (10)	−0.0099 (8)	0.0060 (8)	0.0126 (8)
C12	0.0175 (8)	0.0491 (12)	0.0276 (9)	0.0001 (8)	0.0119 (7)	0.0121 (8)
C13	0.0183 (8)	0.0298 (9)	0.0223 (8)	0.0012 (7)	0.0108 (7)	0.0031 (7)
O1	0.081 (2)	0.0370 (13)	0.082 (2)	0.000	0.059 (2)	0.000

Geometric parameters (Å, º)

Sn1—C1	2.093 (2)	C6—H61	0.9600
Sn1—C8	2.1408 (15)	C6—H62	0.9600
Sn1—C8^i	2.1408 (15)	C6—H63	0.9600
Sn1—N1^i	2.4397 (14)	C7—H71	0.9600
Sn1—N1	2.4398 (14)	C7—H72	0.9600
N1—C7	1.489 (2)	C7—H73	0.9600
N1—C5	1.493 (2)	C8—C13	1.403 (2)
N1—C6	1.497 (2)	C8—C9	1.404 (2)
C1—C2	1.400 (2)	C9—C10	1.396 (3)
C1—C2^i	1.400 (2)	C9—H9	0.9300
C2—C3	1.398 (3)	C10—C11	1.386 (3)
C2—C5	1.519 (3)	C10—H10	0.9300
C3—C4	1.396 (3)	C11—C12	1.390 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C3^i	1.396 (3)	C12—C13	1.401 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—H51	0.9700	C13—H13	0.9300
C5—H52	0.9700	O1—H1	0.80 (3)
C1—Sn1—C8	124.95 (4)	C2—C5—H52	109.4
C1—Sn1—C8^i	124.95 (4)	H51—C5—H52	108.0
C8—Sn1—C8^i	110.09 (9)	N1—C6—H61	109.5
C1—Sn1—N1^i	76.09 (3)	N1—C6—H62	109.5
C8—Sn1—N1^i	96.36 (5)	H61—C6—H62	109.5
C8^i—Sn1—N1^i	99.48 (5)	N1—C6—H63	109.5
C1—Sn1—N1	76.09 (3)	H61—C6—H63	109.5
C8—Sn1—N1	99.48 (5)	H62—C6—H63	109.5
C8^i—Sn1—N1	96.36 (5)	N1—C7—H71	109.5
N1^i—Sn1—N1	152.18 (7)	N1—C7—H72	109.5
C7—N1—C5	109.53 (14)	H71—C7—H72	109.5
C7—N1—C6	108.21 (14)	N1—C7—H73	109.5
C5—N1—C6	109.05 (13)	H71—C7—H73	109.5
C7—N1—Sn1	117.38 (11)	H72—C7—H73	109.5
C5—N1—Sn1	105.28 (10)	C13—C8—C9	118.70 (15)
C6—N1—Sn1	107.16 (10)	C13—C8—Sn1	123.58 (12)
C2—C1—C2^i	122.7 (2)	C9—C8—Sn1	117.72 (12)
C2—C1—Sn1	118.67 (11)	C10—C9—C8	120.63 (17)
C2^i—C1—Sn1	118.67 (11)	C10—C9—H9	119.7
C3—C2—C1	118.34 (18)	C8—C9—H9	119.7
C3—C2—C5	122.74 (17)	C11—C10—C9	119.93 (18)
C1—C2—C5	118.87 (15)	C11—C10—H10	120.0
C4—C3—C2	119.45 (19)	C9—C10—H10	120.0
C4—C3—H3	120.3	C10—C11—C12	120.45 (17)
C2—C3—H3	120.3	C10—C11—H11	119.8
C3^i—C4—C3	121.8 (2)	C12—C11—H11	119.8
C3^i—C4—H4	119.1	C11—C12—C13	119.86 (18)
C3—C4—H4	119.1	C11—C12—H12	120.1
N1—C5—C2	111.31 (13)	C13—C12—H12	120.1
N1—C5—H51	109.4	C12—C13—C8	120.42 (17)
C2—C5—H51	109.4	C12—C13—H13	119.8
N1—C5—H52	109.4	C8—C13—H13	119.8
C1—Sn1—N1—C7	−146.91 (13)	C1—C2—C3—C4	0.3 (2)
C8—Sn1—N1—C7	−23.05 (13)	C5—C2—C3—C4	177.61 (13)
C8^i—Sn1—N1—C7	88.60 (13)	C2—C3—C4—C3^i	−0.16 (11)
N1^i—Sn1—N1—C7	−146.91 (13)	C7—N1—C5—C2	159.57 (14)
C1—Sn1—N1—C5	−24.79 (9)	C6—N1—C5—C2	−82.19 (16)
C8—Sn1—N1—C5	99.06 (11)	Sn1—N1—C5—C2	32.51 (15)
C8^i—Sn1—N1—C5	−149.28 (10)	C3—C2—C5—N1	156.20 (15)
N1^i—Sn1—N1—C5	−24.79 (9)	C1—C2—C5—N1	−26.51 (19)
C1—Sn1—N1—C6	91.21 (10)	C1—Sn1—C8—C13	34.63 (15)
C8—Sn1—N1—C6	−144.93 (11)	C8^i—Sn1—C8—C13	−145.37 (15)
C8^i—Sn1—N1—C6	−33.28 (12)	N1^i—Sn1—C8—C13	112.08 (14)
N1^i—Sn1—N1—C6	91.22 (10)	N1—Sn1—C8—C13	−44.96 (14)
C8—Sn1—C1—C2	−79.31 (9)	C1—Sn1—C8—C9	−144.23 (11)
C8^i—Sn1—C1—C2	100.69 (9)	C8^i—Sn1—C8—C9	35.77 (11)
N1^i—Sn1—C1—C2	−167.37 (8)	N1^i—Sn1—C8—C9	−66.78 (13)
N1—Sn1—C1—C2	12.63 (8)	N1—Sn1—C8—C9	136.18 (13)
C8—Sn1—C1—C2^i	100.69 (9)	C13—C8—C9—C10	0.3 (3)
C8^i—Sn1—C1—C2^i	−79.31 (9)	Sn1—C8—C9—C10	179.25 (13)
N1^i—Sn1—C1—C2^i	12.63 (8)	C8—C9—C10—C11	0.5 (3)
N1—Sn1—C1—C2^i	−167.37 (8)	C9—C10—C11—C12	−0.7 (3)
C2^i—C1—C2—C3	−0.15 (11)	C10—C11—C12—C13	0.1 (3)
Sn1—C1—C2—C3	179.85 (11)	C11—C12—C13—C8	0.8 (3)
C2^i—C1—C2—C5	−177.56 (16)	C9—C8—C13—C12	−1.0 (2)
Sn1—C1—C2—C5	2.44 (16)	Sn1—C8—C13—C12	−179.83 (12)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Br1	0.80 (3)	2.73 (3)	3.5293 (16)	176 (3)