Crystal structure of allyl-ammonium hydrogen succinate at 100 K.

The asymmetric unit of the title compound, C2H8N(+)·C4H5O4 (-), consists of two allyl-ammonium cations and two hydrogen succinate anions (Z' = 2). One of the cations has a near-perfect syn-periplanar (cis) conformation with an N-C-C-C torsion angle of 0.4 (3)°, while the other is characterized by a gauche conformation and a torsion angle of 102.5 (3)°. Regarding the anions, three out of four carboxilic groups are twisted with respect to the central C-CH2-CH2-C group [dihedral angles = 24.4 (2), 31.2 (2) and 40.4 (2)°], the remaining one being instead almost coplanar, with a dihedral angle of 4.0 (2)°. In the crystal, there are two very short, near linear O-H⋯O hydrogen bonds between anions, with the H atoms shifted notably from the donor O towards the O⋯O midpoint. These O-H⋯O hydrogen bonds form helical chains along the [011] which are further linked to each other through N-H⋯O hydrogen bonds (involving all the available NH groups), forming layers lying parallel to (100).

Related literature

For other crystal structures of succinate salts with amines, see: Bhardwaj et al. (2013 ▶); Bruni et al. (2013 ▶); Khorasani & Fernandes (2012 ▶). For the characteristic structural motifs in ammonium di­carboxyl­ate salts, see: Kashino et al. (1998 ▶); Barnes & Weakley (2000 ▶); MacDonald et al. (2001 ▶); Vaidhyanathan et al. (2001 ▶, 2002 ▶); Saraswathi & Vijayan (2002 ▶); Ejsmont (2007 ▶). Salts of succinic acid and amines have strong N—H⋯O and O—H⋯O hydrogen bonds and are thus used as building blocks for the construction of supra­molecular structures, see: Khorasani et al. (2012 ▶); Lemmerer (2011 ▶). For hydrogen bonding, see: Steiner (2002 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C3H8N+·C4H5O4 −

M = 175.19

Triclinic,

a = 8.5649 (3) Å

b = 9.4364 (3) Å

c = 10.8051 (4) Å

α = 88.838 (3)°

β = 87.482 (3)°

γ = 82.843 (3)°

V = 865.55 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.30 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

5454 measured reflections

3013 independent reflections

2373 reflections with I > 2σI)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.093

S = 1.10

3013 reflections

249 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.50 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/S1600536814015633/bg2532sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015633/bg2532Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015633/bg2532Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814015633/bg2532fig1.tif

The mol­ecular structure of (I), showing 50% displacement ellipsoids. Hydrogen bonds are shown as dotted lines.

Click here for additional data file.

b . DOI: 10.1107/S1600536814015633/bg2532fig2.tif

Packing diagram of (I) viewed along the b axis, showing (sideways) the (100) 2D structure defined by the hydrogen-bonding network (dotted lines).

CCDC reference: 1012134

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

C3H8N+·C4H5O4−	Z = 4
Mr = 175.19	F(000) = 376
Triclinic, P1	Dx = 1.344 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5649 (3) Å	Cell parameters from 5943 reflections
b = 9.4364 (3) Å	θ = 2.9–26.0°
c = 10.8051 (4) Å	µ = 0.11 mm−1
α = 88.838 (3)°	T = 100 K
β = 87.482 (3)°	Prism, colourless
γ = 82.843 (3)°	0.30 × 0.20 × 0.15 mm
V = 865.55 (5) Å3

Oxford Diffraction Xcalibur diffractometer	2373 reflections with I > 2σI)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 25.0°, θmin = 2.9°
ω–scan	h = −10→10
5454 measured reflections	k = −11→11
3013 independent reflections	l = −8→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.1223P] where P = (Fo2 + 2Fc2)/3
3013 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.50 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
N11	0.22162 (17)	0.36564 (17)	0.68154 (14)	0.0143 (3)
H11A	0.240 (2)	0.444 (2)	0.7297 (18)	0.022 (5)*
H11B	0.263 (2)	0.387 (2)	0.601 (2)	0.026 (5)*
H11C	0.275 (3)	0.284 (2)	0.711 (2)	0.035 (6)*
C12	0.0522 (2)	0.34987 (19)	0.67065 (15)	0.0171 (4)
H12A	0.0440	0.2616	0.6284	0.021*
H12B	0.0041	0.4279	0.6199	0.021*
C13	−0.0375 (2)	0.34861 (19)	0.79193 (16)	0.0195 (4)
H13	−0.1441	0.3396	0.7890	0.023*
C14	0.0178 (2)	0.35885 (19)	0.90250 (16)	0.0213 (4)
H14A	0.1236	0.3681	0.9107	0.026*
H14B	−0.0491	0.3569	0.9726	0.026*
N21	0.72616 (18)	0.81019 (17)	0.70187 (15)	0.0163 (3)
H21A	0.670 (3)	0.729 (3)	0.699 (2)	0.053 (7)*
H21B	0.675 (2)	0.880 (2)	0.7549 (18)	0.023 (5)*
H21C	0.734 (3)	0.847 (2)	0.623 (2)	0.037 (6)*
C22	0.8872 (2)	0.7596 (2)	0.74249 (19)	0.0266 (5)
H22A	0.9356	0.6839	0.6888	0.032*
H22B	0.8813	0.7213	0.8263	0.032*
C23	0.9854 (3)	0.8799 (3)	0.7381 (3)	0.0480 (7)
H23	1.0230	0.9037	0.6593	0.058*
C24	1.0244 (3)	0.9520 (3)	0.8213 (3)	0.0649 (9)
H24A	0.9915	0.9347	0.9028	0.078*
H24B	1.0869	1.0241	0.8033	0.078*
O31	0.56273 (14)	0.40484 (12)	0.67627 (10)	0.0164 (3)
O32	0.70239 (14)	0.54666 (12)	0.56148 (10)	0.0167 (3)
C33	0.64907 (19)	0.43020 (17)	0.58151 (15)	0.0129 (4)
C34	0.6844 (2)	0.31171 (17)	0.48796 (15)	0.0156 (4)
H34A	0.6139	0.3315	0.4202	0.019*
H34B	0.7911	0.3127	0.4543	0.019*
C35	0.6679 (2)	0.16362 (18)	0.53950 (16)	0.0195 (4)
H35A	0.7512	0.1369	0.5966	0.023*
H35B	0.5683	0.1670	0.5864	0.023*
C36	0.6745 (2)	0.04877 (18)	0.44309 (15)	0.0142 (4)
O37	0.60445 (14)	0.08573 (12)	0.34227 (10)	0.0178 (3)
H37	0.614 (3)	−0.012 (3)	0.275 (2)	0.060 (7)*
O38	0.73921 (15)	−0.07378 (12)	0.46355 (11)	0.0199 (3)
O41	0.62286 (14)	0.88262 (12)	1.20228 (10)	0.0168 (3)
O42	0.39008 (14)	0.97603 (12)	1.13231 (10)	0.0177 (3)
C43	0.5051 (2)	0.88300 (18)	1.13021 (14)	0.0135 (4)
C44	0.5199 (2)	0.76104 (17)	1.04077 (15)	0.0153 (4)
H44A	0.5367	0.6717	1.0871	0.018*
H44B	0.6118	0.7668	0.9860	0.018*
C45	0.3767 (2)	0.75980 (18)	0.96308 (15)	0.0159 (4)
H45A	0.2854	0.7521	1.0181	0.019*
H45B	0.3586	0.8503	0.9186	0.019*
C46	0.3904 (2)	0.64079 (18)	0.87107 (15)	0.0145 (4)
O47	0.53341 (14)	0.60086 (13)	0.82691 (11)	0.0182 (3)
H47	0.543 (3)	0.518 (3)	0.758 (3)	0.084 (10)*
O48	0.27396 (14)	0.58861 (13)	0.83964 (11)	0.0193 (3)

	U11	U22	U33	U12	U13	U23
N11	0.0163 (8)	0.0133 (8)	0.0138 (8)	−0.0028 (6)	−0.0011 (6)	−0.0018 (6)
C12	0.0158 (9)	0.0179 (9)	0.0181 (9)	−0.0025 (7)	−0.0045 (7)	−0.0022 (7)
C13	0.0149 (9)	0.0204 (10)	0.0235 (10)	−0.0042 (7)	0.0008 (8)	−0.0010 (8)
C14	0.0201 (10)	0.0238 (10)	0.0211 (10)	−0.0081 (8)	0.0034 (8)	0.0000 (8)
N21	0.0194 (8)	0.0115 (8)	0.0177 (8)	−0.0008 (7)	−0.0016 (7)	−0.0008 (7)
C22	0.0207 (10)	0.0257 (11)	0.0321 (11)	0.0027 (8)	−0.0028 (8)	0.0018 (9)
C23	0.0229 (12)	0.0636 (17)	0.0608 (16)	−0.0184 (12)	0.0116 (11)	−0.0269 (14)
C24	0.0543 (18)	0.0384 (16)	0.104 (2)	−0.0198 (13)	0.0227 (17)	−0.0188 (16)
O31	0.0208 (7)	0.0143 (6)	0.0147 (6)	−0.0052 (5)	0.0034 (5)	−0.0038 (5)
O32	0.0240 (7)	0.0115 (6)	0.0155 (6)	−0.0061 (5)	−0.0002 (5)	−0.0009 (5)
C33	0.0129 (8)	0.0136 (9)	0.0125 (8)	−0.0008 (7)	−0.0043 (7)	−0.0006 (7)
C34	0.0190 (9)	0.0133 (9)	0.0146 (9)	−0.0026 (7)	0.0022 (7)	−0.0022 (7)
C35	0.0311 (11)	0.0140 (9)	0.0136 (9)	−0.0027 (8)	−0.0036 (8)	−0.0015 (7)
C36	0.0150 (9)	0.0144 (9)	0.0137 (9)	−0.0042 (7)	0.0015 (7)	−0.0004 (7)
O37	0.0251 (7)	0.0123 (6)	0.0161 (6)	0.0000 (5)	−0.0060 (5)	−0.0037 (5)
O38	0.0294 (7)	0.0124 (6)	0.0169 (6)	0.0024 (5)	−0.0022 (5)	−0.0007 (5)
O41	0.0213 (7)	0.0137 (6)	0.0158 (6)	−0.0016 (5)	−0.0057 (5)	−0.0031 (5)
O42	0.0197 (7)	0.0157 (6)	0.0174 (6)	0.0010 (5)	−0.0019 (5)	−0.0045 (5)
C43	0.0186 (9)	0.0118 (8)	0.0109 (8)	−0.0061 (7)	0.0017 (7)	0.0009 (7)
C44	0.0215 (9)	0.0108 (8)	0.0136 (8)	−0.0021 (7)	−0.0013 (7)	−0.0007 (7)
C45	0.0177 (9)	0.0162 (9)	0.0147 (9)	−0.0053 (7)	0.0015 (7)	−0.0037 (7)
C46	0.0199 (9)	0.0123 (9)	0.0118 (8)	−0.0041 (7)	−0.0002 (7)	0.0020 (7)
O47	0.0195 (7)	0.0168 (7)	0.0188 (6)	−0.0047 (5)	0.0026 (5)	−0.0060 (5)
O48	0.0207 (7)	0.0194 (7)	0.0196 (6)	−0.0087 (5)	−0.0007 (5)	−0.0051 (5)

N11—C12	1.487 (2)	O32—C33	1.253 (2)
N11—H11A	0.94 (2)	C33—C34	1.516 (2)
N11—H11B	0.95 (2)	C34—C35	1.515 (2)
N11—H11C	0.90 (2)	C34—H34A	0.9700
C12—C13	1.490 (2)	C34—H34B	0.9700
C12—H12A	0.9700	C35—C36	1.513 (2)
C12—H12B	0.9700	C35—H35A	0.9700
C13—C14	1.314 (2)	C35—H35B	0.9700
C13—H13	0.9300	C36—O38	1.239 (2)
C14—H14A	0.9300	C36—O37	1.288 (2)
C14—H14B	0.9300	O37—H37	1.18 (3)
N21—C22	1.484 (2)	O41—C43	1.301 (2)
N21—H21A	0.95 (3)	O42—C43	1.235 (2)
N21—H21B	0.93 (2)	C43—C44	1.508 (2)
N21—H21C	0.92 (2)	C44—C45	1.518 (2)
C22—C23	1.494 (3)	C44—H44A	0.9700
C22—H22A	0.9700	C44—H44B	0.9700
C22—H22B	0.9700	C45—C46	1.505 (2)
C23—C24	1.220 (4)	C45—H45A	0.9700
C23—H23	0.9300	C45—H45B	0.9700
C24—H24A	0.9300	C46—O48	1.230 (2)
C24—H24B	0.9300	C46—O47	1.308 (2)
O31—C33	1.273 (2)	O47—H47	1.08 (3)
O31—H47	1.39 (3)
C12—N11—H11A	113.9 (12)	O32—C33—C34	119.48 (14)
C12—N11—H11B	107.5 (12)	O31—C33—C34	116.77 (14)
H11A—N11—H11B	104.3 (16)	C35—C34—C33	114.54 (14)
C12—N11—H11C	110.7 (14)	C35—C34—H34A	108.6
H11A—N11—H11C	110.4 (17)	C33—C34—H34A	108.6
H11B—N11—H11C	109.9 (18)	C35—C34—H34B	108.6
N11—C12—C13	113.82 (14)	C33—C34—H34B	108.6
N11—C12—H12A	108.8	H34A—C34—H34B	107.6
C13—C12—H12A	108.8	C36—C35—C34	114.80 (14)
N11—C12—H12B	108.8	C36—C35—H35A	108.6
C13—C12—H12B	108.8	C34—C35—H35A	108.6
H12A—C12—H12B	107.7	C36—C35—H35B	108.6
C14—C13—C12	127.08 (17)	C34—C35—H35B	108.6
C14—C13—H13	116.5	H35A—C35—H35B	107.5
C12—C13—H13	116.5	O38—C36—O37	123.12 (15)
C13—C14—H14A	120.0	O38—C36—C35	121.04 (15)
C13—C14—H14B	120.0	O37—C36—C35	115.80 (15)
H14A—C14—H14B	120.0	C36—O37—H37	110.1 (12)
C22—N21—H21A	108.0 (14)	O42—C43—O41	123.53 (15)
C22—N21—H21B	111.4 (12)	O42—C43—C44	121.67 (15)
H21A—N21—H21B	111.1 (19)	O41—C43—C44	114.79 (14)
C22—N21—H21C	108.6 (14)	C43—C44—C45	113.51 (14)
H21A—N21—H21C	108 (2)	C43—C44—H44A	108.9
H21B—N21—H21C	110.0 (18)	C45—C44—H44A	108.9
N21—C22—C23	110.26 (17)	C43—C44—H44B	108.9
N21—C22—H22A	109.6	C45—C44—H44B	108.9
C23—C22—H22A	109.6	H44A—C44—H44B	107.7
N21—C22—H22B	109.6	C46—C45—C44	114.39 (14)
C23—C22—H22B	109.6	C46—C45—H45A	108.7
H22A—C22—H22B	108.1	C44—C45—H45A	108.7
C24—C23—C22	130.4 (3)	C46—C45—H45B	108.7
C24—C23—H23	114.8	C44—C45—H45B	108.7
C22—C23—H23	114.8	H45A—C45—H45B	107.6
C23—C24—H24A	120.0	O48—C46—O47	123.71 (15)
C23—C24—H24B	120.0	O48—C46—C45	121.43 (15)
H24A—C24—H24B	120.0	O47—C46—C45	114.85 (15)
C33—O31—H47	112.0 (12)	C46—O47—H47	115.2 (16)
O32—C33—O31	123.73 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O48	0.94 (2)	1.89 (2)	2.8275 (19)	174.4 (17)
N11—H11B···O32i	0.95 (2)	1.88 (2)	2.8107 (19)	166.9 (18)
N11—H11C···O41ii	0.90 (2)	1.95 (2)	2.844 (2)	172 (2)
N21—H21A···O32	0.95 (3)	2.28 (3)	2.972 (2)	128.5 (19)
N21—H21A···O47	0.95 (3)	2.21 (3)	2.994 (2)	138.7 (19)
N21—H21B···O42iii	0.93 (2)	1.86 (2)	2.786 (2)	169.2 (17)
N21—H21C···O38iv	0.92 (2)	1.86 (2)	2.7809 (19)	177 (2)
O37—H37···O41v	1.18 (3)	1.28 (3)	2.4510 (15)	180 (3)
O47—H47···O31	1.08 (3)	1.39 (3)	2.4707 (15)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11A⋯O48	0.94 (2)	1.89 (2)	2.8275 (19)	174.4 (17)
N11—H11B⋯O32i	0.95 (2)	1.88 (2)	2.8107 (19)	166.9 (18)
N11—H11C⋯O41ii	0.90 (2)	1.95 (2)	2.844 (2)	172 (2)
N21—H21A⋯O32	0.95 (3)	2.28 (3)	2.972 (2)	128.5 (19)
N21—H21A⋯O47	0.95 (3)	2.21 (3)	2.994 (2)	138.7 (19)
N21—H21B⋯O42iii	0.93 (2)	1.86 (2)	2.786 (2)	169.2 (17)
N21—H21C⋯O38iv	0.92 (2)	1.86 (2)	2.7809 (19)	177 (2)
O37—H37⋯O41v	1.18 (3)	1.28 (3)	2.4510 (15)	180 (3)
O47—H47⋯O31	1.08 (3)	1.39 (3)	2.4707 (15)	176 (3)

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