Allyl-ammonium hydrogen oxalate hemihydrate.

In the title hydrated mol-ecular salt, C3H8N(+)·C2HO4 (-)·0.5H2O, the water O atom lies on a crystallographic twofold axis. The C=C-C-N torsion angle in the cation is 2.8 (3)° and the dihedral angle between the CO2 and CO2H planes in the anion is 1.0 (4)°. In the crystal, the hydrogen oxalate ions are linked by O-H⋯O hydrogen bonds, generating [010] chains. The allyl-ammonium cations bond to the chains through N-H⋯O and N-H⋯(O,O) hydrogen bonds. The water mol-ecule accepts two N-H⋯O hydrogen bonds and makes two O-H⋯O hydrogen bonds. Together, the hydrogen bonds generate (100) sheets.

Related literature

For the crystal structures of oxalic acid salts with aliphatic amines, see: Ejsmont (2006 ▶), (2007 ▶); Ejsmont & Zaleski (2006a ▶,b ▶); Vaidhyanathan et al. (2001 ▶, 2002 ▶); MacDonald et al. (2001 ▶) For information on the Cambridge Database, see: Allen (2002 ▶).

Experimental

Crystal data

C3H8N+·C2HO4 −·0.5H2O

M = 156.14

Monoclinic,

a = 21.578 (3) Å

b = 5.6521 (4) Å

c = 13.8629 (17) Å

β = 118.415 (17)°

V = 1487.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.33 × 0.18 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

4525 measured reflections

1376 independent reflections

958 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.098

S = 0.90

1376 reflections

136 parameters

All H-atom parameters refined

Δρmax = 0.26 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814015190/hb7243sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015190/hb7243Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015190/hb7243Isup3.cml

CCDC reference: 1010915

Additional supporting information: crystallographic information; 3D view; checkCIF report

C3H8N+·C2HO4−·0.5H2O	F(000) = 664
Mr = 156.14	Dx = 1.395 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4525 reflections
a = 21.578 (3) Å	θ = 3.3–25.5°
b = 5.6521 (4) Å	µ = 0.12 mm−1
c = 13.8629 (17) Å	T = 100 K
β = 118.415 (17)°	Prism, colourless
V = 1487.0 (3) Å3	0.33 × 0.18 × 0.14 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer	958 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 25.5°, θmin = 3.3°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1	h = −26→26
ω–scan	k = −6→5
4525 measured reflections	l = −16→16
1376 independent 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	All H-atom parameters refined
S = 0.90	w = 1/[σ2(Fo2) + (0.0628P)2] where P = (Fo2 + 2Fc2)/3
1376 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.40092 (10)	0.2394 (3)	0.23240 (15)	0.0196 (4)
H1A	0.4411 (13)	0.348 (4)	0.2556 (19)	0.033 (6)*
H1B	0.4018 (14)	0.132 (5)	0.177 (2)	0.050 (8)*
H1C	0.4052 (14)	0.154 (5)	0.291 (2)	0.046 (8)*
C2	0.33560 (12)	0.3802 (4)	0.18227 (19)	0.0231 (5)
H2A	0.3367 (11)	0.466 (4)	0.1271 (18)	0.021 (5)*
H2B	0.3376 (12)	0.486 (4)	0.233 (2)	0.032 (6)*
C3	0.27053 (13)	0.2364 (4)	0.13940 (19)	0.0284 (5)
H3	0.2311 (12)	0.325 (4)	0.1035 (18)	0.026 (6)*
C4	0.26561 (15)	0.0080 (5)	0.1452 (2)	0.0327 (6)
H4A	0.2203 (14)	−0.075 (4)	0.111 (2)	0.042 (7)*
H4B	0.3053 (13)	−0.085 (4)	0.1769 (19)	0.028 (6)*
C5	0.41682 (10)	0.1591 (3)	−0.03835 (16)	0.0167 (5)
C6	0.41572 (10)	−0.0892 (3)	0.00740 (16)	0.0177 (5)
O7	0.41788 (8)	0.3311 (2)	0.02573 (11)	0.0211 (4)
H7	0.4173 (16)	0.482 (6)	−0.002 (3)	0.077 (10)*
O8	0.41599 (8)	0.1838 (2)	−0.12581 (11)	0.0228 (4)
O9	0.41549 (8)	−0.1043 (2)	0.09658 (11)	0.0231 (4)
O10	0.41539 (8)	−0.2570 (2)	−0.05214 (11)	0.0221 (4)
O11	0.5000	0.5720 (4)	0.2500	0.0199 (5)
H11	0.5269 (14)	0.672 (5)	0.302 (2)	0.055 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0289 (11)	0.0222 (10)	0.0119 (8)	−0.0017 (8)	0.0133 (8)	0.0000 (8)
C2	0.0356 (13)	0.0234 (12)	0.0166 (11)	0.0039 (10)	0.0175 (10)	0.0007 (10)
C3	0.0273 (14)	0.0331 (14)	0.0255 (12)	0.0051 (11)	0.0132 (11)	0.0020 (10)
C4	0.0290 (14)	0.0362 (15)	0.0294 (13)	−0.0024 (12)	0.0110 (11)	0.0021 (12)
C5	0.0189 (11)	0.0201 (10)	0.0113 (10)	−0.0001 (8)	0.0073 (8)	−0.0027 (8)
C6	0.0202 (11)	0.0194 (10)	0.0136 (10)	0.0009 (8)	0.0082 (9)	−0.0002 (8)
O7	0.0383 (9)	0.0158 (7)	0.0148 (7)	−0.0003 (7)	0.0172 (7)	0.0003 (6)
O8	0.0394 (9)	0.0224 (8)	0.0128 (7)	−0.0011 (6)	0.0173 (7)	0.0005 (6)
O9	0.0416 (9)	0.0222 (8)	0.0145 (8)	0.0049 (6)	0.0206 (7)	0.0037 (6)
O10	0.0395 (9)	0.0172 (7)	0.0148 (7)	−0.0003 (6)	0.0170 (7)	−0.0014 (6)
O11	0.0283 (12)	0.0207 (11)	0.0119 (10)	0.000	0.0107 (9)	0.000

N1—C2	1.473 (3)	C4—H4A	0.98 (3)
N1—H1A	0.98 (3)	C4—H4B	0.92 (2)
N1—H1B	0.98 (3)	C5—O8	1.212 (2)
N1—H1C	0.91 (3)	C5—O7	1.309 (2)
C2—C3	1.480 (3)	C5—C6	1.545 (3)
C2—H2A	0.92 (2)	C6—O9	1.242 (2)
C2—H2B	0.91 (2)	C6—O10	1.255 (2)
C3—C4	1.301 (3)	O7—H7	0.94 (3)
C3—H3	0.91 (2)	O11—H11	0.88 (3)
C2—N1—H1A	108.3 (13)	C4—C3—H3	120.1 (14)
C2—N1—H1B	109.5 (15)	C2—C3—H3	112.3 (14)
H1A—N1—H1B	108 (2)	C3—C4—H4A	122.4 (14)
C2—N1—H1C	112.2 (17)	C3—C4—H4B	120.8 (14)
H1A—N1—H1C	110 (2)	H4A—C4—H4B	116.6 (19)
H1B—N1—H1C	109 (2)	O8—C5—O7	125.49 (18)
N1—C2—C3	113.87 (18)	O8—C5—C6	121.27 (17)
N1—C2—H2A	106.4 (13)	O7—C5—C6	113.24 (15)
C3—C2—H2A	110.6 (13)	O9—C6—O10	126.98 (18)
N1—C2—H2B	108.0 (14)	O9—C6—C5	118.63 (16)
C3—C2—H2B	111.1 (15)	O10—C6—C5	114.39 (16)
H2A—C2—H2B	106.5 (19)	C5—O7—H7	113.9 (19)
C4—C3—C2	127.6 (2)
N1—C2—C3—C4	2.8 (3)	O8—C5—C6—O10	1.4 (3)
O8—C5—C6—O9	−178.8 (2)	O7—C5—C6—O10	−179.34 (17)
O7—C5—C6—O9	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O9	0.98 (3)	1.86 (3)	2.825 (2)	169 (2)
N1—H1A···O11	0.98 (3)	1.82 (3)	2.769 (2)	161 (2)
N1—H1C···O8i	0.91 (3)	2.19 (3)	3.014 (2)	151 (2)
N1—H1C···O10i	0.91 (3)	2.16 (3)	2.853 (2)	132 (2)
O7—H7···O10ii	0.94 (3)	1.62 (3)	2.5563 (19)	179 (4)
O11—H11···O9iii	0.88 (3)	1.86 (3)	2.739 (2)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O9	0.98 (3)	1.86 (3)	2.825 (2)	169 (2)
N1—H1A⋯O11	0.98 (3)	1.82 (3)	2.769 (2)	161 (2)
N1—H1C⋯O8i	0.91 (3)	2.19 (3)	3.014 (2)	151 (2)
N1—H1C⋯O10i	0.91 (3)	2.16 (3)	2.853 (2)	132 (2)
O7—H7⋯O10ii	0.94 (3)	1.62 (3)	2.5563 (19)	179 (4)
O11—H11⋯O9iii	0.88 (3)	1.86 (3)	2.739 (2)	176 (3)

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