(S)-2-Oxotetra-hydro-furan-3-aminium bromide.

In the title HBr salt of (S)-homoserine lactone, C(4)H(8)NO(2) (+)·Br(-), the five-membered ring has an envelope conformation, with the -CH(2)- C atom adjacent to the N-substituted C atom at the flap position. The four-atom mean plane (r.m.s. deviation = 0.005 Å) of the envelope forms a dihedral angle of 32.12 (9)° with the three-atom flap plane. The distorted square-pyramidal coordination about the anion involves five surrounding cations, with the square base defined by three N-H⋯Br hydrogen bonds [Br⋯N = 3.3046 (10), 3.3407 (12) and 3.3644 (13) Å] and near-contact with an H atom attached to C [Br⋯C = 3.739 (1) Å]. Another Br⋯C contact of 3.427 (1) Å defines the apex. There is also an N-H⋯O hydrogen bond present linking the cations.

Related literature

For related crystal structures, see: Bocelli & Grenier-Loustalot (1981 ▶); Papaioannou et al. (1990 ▶). For the synthesis of the title compound, see: Armstrong (1948 ▶); Cowell (1996 ▶). For the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C4H8NO2 +·Br−

M = 182.02

Orthorhombic,

a = 6.1425 (1) Å

b = 9.4196 (2) Å

c = 11.0394 (3) Å

V = 638.74 (2) Å3

Z = 4

Mo Kα radiation

μ = 6.35 mm−1

T = 90 K

0.25 × 0.25 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.300, T max = 0.336

4072 measured reflections

4072 independent reflections

3915 reflections with I > 2σ(I)

R int = 0

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.049

S = 1.07

4072 reflections

76 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.74 e Å−3

Absolute structure: Flack (1983 ▶) and Hooft et al. (2008 ▶), with 1724 Friedel pairs

Flack parameter: 0.030 (7)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: IDEAL (Gould et al., 1988 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032552/zq2176sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032552/zq2176Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032552/zq2176Isup3.cml

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

C4H8NO2+·Br−	Dx = 1.893 Mg m−3
Mr = 182.02	Melting point: 514 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2320 reflections
a = 6.1425 (1) Å	θ = 2.6–41.2°
b = 9.4196 (2) Å	µ = 6.35 mm−1
c = 11.0394 (3) Å	T = 90 K
V = 638.74 (2) Å3	Prism, colourless
Z = 4	0.25 × 0.25 × 0.22 mm
F(000) = 360

Nonius KappaCCD diffractometer	4072 independent reflections
Radiation source: sealed tube	3915 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0
Detector resolution: 9 pixels mm-1	θmax = 40.8°, θmin = 2.8°
CCD rotation images, thick slices scans	h = −11→11
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −16→17
Tmin = 0.300, Tmax = 0.336	l = −20→20
4072 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.022	w = 1/[σ2(Fo2) + (0.0124P)2 + 0.6239P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.049	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.68 e Å−3
4072 reflections	Δρmin = −0.74 e Å−3
76 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0198 (9)
0 constraints	Absolute structure: Flack (1983) and Hooft et al. (2008), with 1724 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.030 (7)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
Br1	0.398524 (19)	−0.035758 (13)	−0.012904 (11)	0.00918 (3)
C1	0.73144 (19)	−0.01395 (12)	0.23546 (12)	0.00862 (18)
C2	0.64286 (18)	0.13091 (12)	0.27008 (11)	0.00776 (17)
H2	0.505	0.1494	0.2246	0.009*
C3	0.8183 (2)	0.23236 (13)	0.22670 (12)	0.01110 (19)
H3A	0.9319	0.2468	0.2891	0.013*
H3B	0.7564	0.3254	0.2032	0.013*
C4	0.9071 (3)	0.15234 (14)	0.11731 (11)	0.01289 (19)
H4A	0.8245	0.1772	0.0433	0.015*
H4B	1.0626	0.1752	0.1042	0.015*
N1	0.5994 (2)	0.13823 (11)	0.40235 (9)	0.00966 (14)
H1A	0.4755	0.0892	0.4197	0.014*
H1B	0.5828	0.2305	0.4249	0.014*
H1C	0.7131	0.0994	0.4435	0.014*
O1	0.87958 (17)	0.00107 (10)	0.14696 (9)	0.01107 (15)
O2	0.68198 (18)	−0.12734 (10)	0.27816 (10)	0.01255 (16)

	U11	U22	U33	U12	U13	U23
Br1	0.00741 (4)	0.00830 (4)	0.01182 (4)	−0.00006 (4)	−0.00068 (3)	0.00165 (3)
C1	0.0080 (4)	0.0070 (5)	0.0109 (4)	−0.0001 (3)	−0.0007 (3)	−0.0011 (3)
C2	0.0082 (4)	0.0052 (4)	0.0099 (4)	0.0006 (3)	0.0002 (3)	−0.0001 (3)
C3	0.0133 (5)	0.0066 (4)	0.0134 (5)	−0.0012 (4)	0.0025 (4)	0.0011 (3)
C4	0.0159 (5)	0.0101 (4)	0.0126 (4)	−0.0012 (5)	0.0040 (5)	0.0010 (3)
N1	0.0093 (3)	0.0084 (3)	0.0112 (4)	−0.0007 (4)	0.0026 (4)	−0.0013 (3)
O1	0.0120 (4)	0.0086 (3)	0.0126 (3)	0.0003 (3)	0.0033 (3)	−0.0017 (3)
O2	0.0132 (4)	0.0063 (3)	0.0181 (4)	−0.0017 (3)	−0.0006 (3)	0.0009 (3)

C1—O2	1.2063 (15)	C3—H3B	0.99
C1—O1	1.3427 (16)	C4—O1	1.4717 (16)
C1—C2	1.5179 (17)	C4—H4A	0.99
C2—N1	1.4861 (16)	C4—H4B	0.99
C2—C3	1.5178 (17)	N1—H1A	0.91
C2—H2	1	N1—H1B	0.91
C3—C4	1.5244 (18)	N1—H1C	0.91
C3—H3A	0.99
O2—C1—O1	123.25 (12)	C4—C3—H3B	111.6
O2—C1—C2	127.40 (12)	H3A—C3—H3B	109.4
O1—C1—C2	109.35 (10)	O1—C4—C3	105.16 (10)
O2—C1—Br1	96.27 (8)	O1—C4—H4A	110.7
O1—C1—Br1	80.12 (7)	C3—C4—H4A	110.7
C2—C1—Br1	92.37 (7)	O1—C4—H4B	110.7
N1—C2—C1	110.70 (10)	C3—C4—H4B	110.7
N1—C2—C3	114.11 (10)	H4A—C4—H4B	108.8
C1—C2—C3	103.42 (10)	C2—N1—H1A	109.5
N1—C2—H2	109.5	C2—N1—H1B	109.5
C1—C2—H2	109.5	H1A—N1—H1B	109.5
C3—C2—H2	109.5	C2—N1—H1C	109.5
C2—C3—C4	101.11 (10)	H1A—N1—H1C	109.5
C2—C3—H3A	111.6	H1B—N1—H1C	109.5
C4—C3—H3A	111.6	C1—O1—C4	109.98 (10)
C2—C3—H3B	111.6
O2—C1—C2—N1	35.80 (17)	C1—C2—C3—C4	31.16 (13)
O1—C1—C2—N1	−144.09 (10)	C2—C3—C4—O1	−31.04 (14)
Br1—C1—C2—N1	135.54 (8)	O2—C1—O1—C4	−178.50 (13)
O2—C1—C2—C3	158.41 (13)	C2—C1—O1—C4	1.40 (14)
O1—C1—C2—C3	−21.48 (13)	Br1—C1—O1—C4	90.45 (9)
Br1—C1—C2—C3	−101.84 (8)	C3—C4—O1—C1	19.30 (15)
N1—C2—C3—C4	151.48 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1i	0.91	2.47	3.3407 (12)	161
N1—H1B···Br1ii	0.91	2.41	3.3046 (10)	168
N1—H1C···Br1iii	0.91	2.51	3.3644 (13)	157
N1—H1C···O1iii	0.91	2.5	3.0050 (14)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1i	0.91	2.47	3.3407 (12)	161
N1—H1B⋯Br1ii	0.91	2.41	3.3046 (10)	168
N1—H1C⋯Br1iii	0.91	2.51	3.3644 (13)	157
N1—H1C⋯O1iii	0.91	2.5	3.0050 (14)	115

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