Bis[2-(ethoxy-carbonyl-amino)ethan-aminium] hexa-bromidostannate.

In the title salt, (C(5)H(13)N(2)O(2))(2)[SnBr(6)], the Sn atom (site symmetry ) exists in a slightly distorted octa-hedral geometry. The cation is non-planar as the terminal CH(2)NH(3) (+) residue lies below the plane defined by the remaining non-H atoms. In the crystal, cations associate via N-H⋯O hydrogen bonds involving the ammonium and carbonyl residues, forming a 14-membered {⋯HNC(2)NCO}(2) synthon. The cations and anions are arranged in alternating layers arranged along the a-axis direction, the major association between them being N-H⋯Br contacts.

Related literature

For background to the synthesis of the title salt, see: Duschinsky (1950 ▶); Kita et al. (1980 ▶); Smith et al. (1998 ▶); Tavridou et al. (1995 ▶); Wilson & Nowick (1998 ▶).

Experimental

Crystal data

(C5H13N2O2)2[SnBr6]

M = 864.48

Monoclinic,

a = 21.8907 (5) Å

b = 7.4428 (2) Å

c = 15.5318 (4) Å

β = 105.934 (2)°

V = 2433.34 (11) Å3

Z = 4

Mo Kα radiation

μ = 10.92 mm−1

T = 120 K

0.38 × 0.32 × 0.22 mm

Data collection

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.355, T max = 0.746

15137 measured reflections

2777 independent reflections

2450 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.070

S = 1.12

2777 reflections

120 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −1.35 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904687X/hb5214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904687X/hb5214Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C5H13N2O2)2[SnBr6]	F(000) = 1624
Mr = 864.48	Dx = 2.360 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 11507 reflections
a = 21.8907 (5) Å	θ = 2.9–27.5°
b = 7.4428 (2) Å	µ = 10.92 mm−1
c = 15.5318 (4) Å	T = 120 K
β = 105.934 (2)°	Block, light-yellow
V = 2433.34 (11) Å3	0.38 × 0.32 × 0.22 mm
Z = 4

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	2777 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2450 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.1°
φ and ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
Tmin = 0.355, Tmax = 0.746	l = −20→20
15137 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0263P)2 + 9.0406P] where P = (Fo2 + 2Fc2)/3
2777 reflections	(Δ/σ)max = 0.001
120 parameters	Δρmax = 0.87 e Å−3
1 restraint	Δρmin = −1.35 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Sn	0.2500	0.2500	0.5000	0.01268 (10)
Br1	0.220893 (18)	0.02595 (5)	0.61162 (3)	0.02190 (11)
Br2	0.135158 (17)	0.22636 (5)	0.39826 (3)	0.02122 (11)
Br3	0.284421 (16)	−0.01941 (5)	0.41692 (3)	0.01712 (11)
O1	−0.02161 (12)	0.3062 (4)	0.6285 (2)	0.0235 (6)
O2	0.01221 (13)	0.2554 (4)	0.5051 (2)	0.0224 (6)
N1	0.08208 (14)	0.3322 (5)	0.6316 (2)	0.0200 (7)
H1N	0.1073	0.3259	0.5963	0.024*
N2	0.14598 (16)	0.2592 (4)	0.8785 (2)	0.0183 (7)
H2N	0.1749	0.3501	0.8905	0.027*
H3N	0.1627	0.1606	0.9111	0.027*
H4N	0.1103	0.2942	0.8931	0.027*
C1	−0.0502 (2)	0.1802 (6)	0.3600 (3)	0.0277 (10)
H1A	−0.0323	0.2857	0.3379	0.042*
H1B	−0.0933	0.1584	0.3219	0.042*
H1C	−0.0235	0.0751	0.3584	0.042*
C2	−0.05232 (18)	0.2130 (6)	0.4539 (3)	0.0212 (9)
H2A	−0.0812	0.3143	0.4561	0.025*
H2B	−0.0677	0.1047	0.4785	0.025*
C3	0.02071 (18)	0.2985 (5)	0.5912 (3)	0.0163 (8)
C4	0.10453 (17)	0.3786 (5)	0.7254 (3)	0.0187 (8)
H4A	0.0693	0.4315	0.7455	0.022*
H4B	0.1387	0.4695	0.7339	0.022*
C5	0.1296 (2)	0.2146 (6)	0.7810 (3)	0.0227 (9)
H5A	0.0971	0.1185	0.7674	0.027*
H5B	0.1679	0.1695	0.7657	0.027*

	U11	U22	U33	U12	U13	U23
Sn	0.01042 (17)	0.01213 (17)	0.0158 (2)	0.00012 (12)	0.00415 (14)	−0.00043 (13)
Br1	0.0233 (2)	0.01857 (19)	0.0286 (2)	0.00387 (15)	0.01518 (17)	0.00774 (16)
Br2	0.01230 (18)	0.0248 (2)	0.0236 (2)	0.00109 (15)	−0.00008 (16)	−0.00413 (16)
Br3	0.01406 (18)	0.01542 (18)	0.0230 (2)	−0.00038 (14)	0.00701 (15)	−0.00511 (15)
O1	0.0150 (13)	0.0372 (16)	0.0200 (16)	−0.0028 (12)	0.0075 (11)	−0.0051 (13)
O2	0.0141 (13)	0.0355 (17)	0.0170 (15)	0.0003 (11)	0.0034 (12)	−0.0037 (12)
N1	0.0116 (14)	0.0328 (19)	0.0161 (18)	−0.0009 (14)	0.0046 (13)	0.0002 (15)
N2	0.0125 (14)	0.0211 (16)	0.0195 (18)	0.0017 (12)	0.0016 (13)	−0.0030 (13)
C1	0.031 (2)	0.026 (2)	0.023 (2)	0.0041 (19)	0.0008 (18)	−0.0024 (18)
C2	0.0159 (18)	0.026 (2)	0.017 (2)	0.0009 (16)	−0.0038 (16)	−0.0016 (17)
C3	0.0164 (18)	0.0160 (17)	0.016 (2)	0.0001 (15)	0.0044 (15)	−0.0005 (15)
C4	0.0158 (17)	0.0199 (18)	0.019 (2)	−0.0042 (15)	0.0034 (15)	−0.0015 (16)
C5	0.0205 (19)	0.028 (2)	0.017 (2)	0.0045 (17)	−0.0002 (16)	−0.0079 (17)

Sn—Br2i	2.5820 (4)	N2—H3N	0.9100
Sn—Br2	2.5820 (4)	N2—H4N	0.9100
Sn—Br3	2.6053 (4)	C1—C2	1.493 (6)
Sn—Br3i	2.6053 (4)	C1—H1A	0.9800
Sn—Br1i	2.6075 (4)	C1—H1B	0.9800
Sn—Br1	2.6075 (4)	C1—H1C	0.9800
O1—C3	1.222 (5)	C2—H2A	0.9900
O2—C3	1.339 (5)	C2—H2B	0.9900
O2—C2	1.453 (5)	C4—C5	1.509 (6)
N1—C3	1.341 (5)	C4—H4A	0.9900
N1—C4	1.445 (5)	C4—H4B	0.9900
N1—H1N	0.8800	C5—H5A	0.9900
N2—C5	1.494 (5)	C5—H5B	0.9900
N2—H2N	0.9100
Br2i—Sn—Br2	180.000 (10)	C2—C1—H1B	109.5
Br2i—Sn—Br3	89.437 (12)	H1A—C1—H1B	109.5
Br2—Sn—Br3	90.563 (12)	C2—C1—H1C	109.5
Br2i—Sn—Br3i	90.563 (12)	H1A—C1—H1C	109.5
Br2—Sn—Br3i	89.437 (12)	H1B—C1—H1C	109.5
Br3—Sn—Br3i	180.0	O2—C2—C1	106.4 (3)
Br2i—Sn—Br1i	89.357 (13)	O2—C2—H2A	110.4
Br2—Sn—Br1i	90.643 (13)	C1—C2—H2A	110.4
Br3—Sn—Br1i	90.355 (12)	O2—C2—H2B	110.4
Br3i—Sn—Br1i	89.645 (12)	C1—C2—H2B	110.4
Br2i—Sn—Br1	90.643 (13)	H2A—C2—H2B	108.6
Br2—Sn—Br1	89.357 (13)	O1—C3—O2	124.8 (3)
Br3—Sn—Br1	89.646 (12)	O1—C3—N1	124.2 (4)
Br3i—Sn—Br1	90.354 (12)	O2—C3—N1	111.0 (3)
Br1i—Sn—Br1	180.000 (16)	N1—C4—C5	110.7 (3)
C3—O2—C2	116.5 (3)	N1—C4—H4A	109.5
C3—N1—C4	122.4 (3)	C5—C4—H4A	109.5
C3—N1—H1N	114.7	N1—C4—H4B	109.5
C4—N1—H1N	122.9	C5—C4—H4B	109.5
C5—N2—H2N	109.5	H4A—C4—H4B	108.1
C5—N2—H3N	109.5	N2—C5—C4	110.4 (3)
H2N—N2—H3N	109.5	N2—C5—H5A	109.6
C5—N2—H4N	109.5	C4—C5—H5A	109.6
H2N—N2—H4N	109.5	N2—C5—H5B	109.6
H3N—N2—H4N	109.5	C4—C5—H5B	109.6
C2—C1—H1A	109.5	H5A—C5—H5B	108.1
C3—O2—C2—C1	176.8 (3)	C4—N1—C3—O2	−178.8 (3)
C2—O2—C3—O1	−0.8 (6)	C3—N1—C4—C5	96.4 (4)
C2—O2—C3—N1	179.1 (3)	N1—C4—C5—N2	−173.7 (3)
C4—N1—C3—O1	1.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···Br3i	0.88	2.83	3.501 (3)	134
N2—H2n···Br1ii	0.91	2.64	3.495 (3)	157
N2—H3n···Br3iii	0.91	2.84	3.425 (3)	123
N2—H4n···O1iv	0.91	1.88	2.717 (5)	152

Table 1

Selected bond lengths (Å)

Sn—Br2	2.5820 (4)
Sn—Br3	2.6053 (4)
Sn—Br1	2.6075 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯Br3i	0.88	2.83	3.501 (3)	134
N2—H2n⋯Br1ii	0.91	2.64	3.495 (3)	157
N2—H3n⋯Br3iii	0.91	2.84	3.425 (3)	123
N2—H4n⋯O1iv	0.91	1.88	2.717 (5)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .