Anilinium 3-(4-hy-droxy-3-meth-oxy-phenyl)prop-2-enoate.

The structure of the title salt, C(6)H(8)N(+)·C(10)H(9)O(4) (-), is stabilized by N-H⋯O and O-H⋯O hydrogen bonding between 3-(4-hy-droxy-3-meth-oxy-phen-yl)prop-2-enoate anions and anilinium cations, which links the components into a two-dimensional array.

Related literature

For ferulic acid [3-(4-hy­droxy-3-meth­oxy­phen­yl)-2-propenoic acid] and its pharmacological activity, see: Hirabayashi et al. (1995 ▶); Liyama et al. (1994 ▶); Nomura et al. (2003 ▶); Ogiwara et al. (2002 ▶); Ou et al. (2003 ▶). For crystal structures on hydrogen-bond motifs in organic ammonium salts, see: Ni et al. (2007 ▶); Smith et al. (2004 ▶).

Experimental

Crystal data

C6H8N+·C10H9O4 −

M = 287.31

Orthorhombic,

a = 6.2047 (7) Å

b = 8.2668 (9) Å

c = 28.790 (3) Å

V = 1476.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.30 × 0.28 × 0.25 mm

Data collection

Bruker APEXII area-detector diffractometer

7666 measured reflections

1586 independent reflections

1325 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.079

S = 1.04

1586 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 datablocks I, global. DOI: 10.1107/S1600536810043412/om2374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043412/om2374Isup2.hkl

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

C6H8N+·C10H9O4−	F(000) = 608
Mr = 287.31	Dx = 1.292 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2062 reflections
a = 6.2047 (7) Å	θ = 2.6–23.1°
b = 8.2668 (9) Å	µ = 0.09 mm−1
c = 28.790 (3) Å	T = 296 K
V = 1476.7 (3) Å3	Block, colourless
Z = 4	0.30 × 0.28 × 0.25 mm

Bruker APEXII area-detector diffractometer	1325 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 25.2°, θmin = 2.6°
φ and ω scans	h = −7→7
7666 measured reflections	k = −9→6
1586 independent reflections	l = −32→34

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.170P] where P = (Fo2 + 2Fc2)/3
1586 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.11 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
C1	0.3231 (5)	0.4376 (3)	0.92787 (9)	0.0626 (7)
H1	0.2083	0.5019	0.9183	0.075*
C2	0.3238 (7)	0.2733 (4)	0.91830 (10)	0.0799 (10)
H2	0.2092	0.2272	0.9022	0.096*
C3	0.4919 (7)	0.1789 (4)	0.93232 (10)	0.0794 (10)
H3	0.4919	0.0687	0.9258	0.095*
C4	0.6609 (7)	0.2469 (4)	0.95602 (11)	0.0792 (9)
H4	0.7752	0.1823	0.9657	0.095*
C5	0.6628 (5)	0.4108 (3)	0.96573 (9)	0.0609 (7)
H5	0.7778	0.4570	0.9817	0.073*
C6	0.4920 (4)	0.5044 (3)	0.95139 (7)	0.0422 (5)
C7	0.8501 (4)	1.0202 (3)	0.79047 (7)	0.0434 (6)
C8	0.6513 (4)	1.0959 (3)	0.79226 (7)	0.0494 (6)
H8	0.5777	1.1016	0.8204	0.059*
C9	0.5597 (4)	1.1639 (3)	0.75247 (8)	0.0509 (6)
H9	0.4288	1.2185	0.7543	0.061*
C10	0.6649 (4)	1.1496 (3)	0.71042 (7)	0.0447 (6)
C11	0.8608 (4)	1.0664 (3)	0.70800 (7)	0.0417 (6)
C12	0.9540 (4)	1.0060 (3)	0.74787 (8)	0.0443 (6)
H12	1.0876	0.9553	0.7463	0.053*
C13	0.9606 (4)	0.9557 (3)	0.83187 (7)	0.0451 (6)
H13	1.1098	0.9473	0.8299	0.054*
C14	0.8738 (4)	0.9089 (3)	0.87121 (7)	0.0437 (6)
H14	0.7250	0.9167	0.8744	0.052*
C15	0.9992 (4)	0.8447 (3)	0.91045 (7)	0.0375 (5)
C16	1.1413 (5)	0.9702 (4)	0.65865 (9)	0.0711 (9)
H16A	1.1252	0.8615	0.6698	0.107*
H16B	1.2524	1.0238	0.6760	0.107*
H16C	1.1798	0.9681	0.6264	0.107*
N1	0.4930 (3)	0.6767 (2)	0.96199 (5)	0.0411 (5)
H1A	0.4750	0.6908	0.9924	0.062*
H1B	0.3863	0.7252	0.9467	0.062*
H1C	0.6184	0.7195	0.9533	0.062*
O1	1.2000 (3)	0.8328 (2)	0.90760 (5)	0.0467 (4)
O2	0.8938 (3)	0.8013 (2)	0.94615 (5)	0.0536 (5)
O3	0.5753 (3)	1.2193 (3)	0.67198 (5)	0.0578 (5)
H3A	0.6647	1.2222	0.6510	0.087*
O4	0.9441 (3)	1.0547 (2)	0.66423 (5)	0.0535 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0678 (18)	0.0590 (18)	0.0609 (16)	−0.0043 (16)	−0.0183 (15)	−0.0011 (14)
C2	0.105 (3)	0.0604 (19)	0.0737 (19)	−0.014 (2)	−0.012 (2)	−0.0107 (17)
C3	0.116 (3)	0.0483 (17)	0.074 (2)	0.002 (2)	0.025 (2)	−0.0048 (16)
C4	0.084 (2)	0.063 (2)	0.091 (2)	0.0227 (19)	0.013 (2)	0.0134 (17)
C5	0.0573 (18)	0.0609 (18)	0.0644 (16)	0.0078 (16)	−0.0051 (14)	0.0067 (15)
C6	0.0482 (14)	0.0475 (14)	0.0309 (11)	0.0000 (12)	0.0042 (11)	0.0030 (10)
C7	0.0476 (14)	0.0472 (14)	0.0353 (11)	0.0003 (12)	−0.0062 (11)	0.0048 (10)
C8	0.0545 (16)	0.0578 (15)	0.0358 (12)	0.0016 (14)	0.0036 (12)	0.0035 (12)
C9	0.0449 (14)	0.0592 (16)	0.0486 (13)	0.0042 (13)	−0.0044 (12)	0.0063 (12)
C10	0.0461 (14)	0.0510 (14)	0.0370 (12)	−0.0037 (13)	−0.0093 (11)	0.0065 (11)
C11	0.0457 (14)	0.0442 (13)	0.0352 (11)	−0.0001 (12)	−0.0049 (10)	0.0044 (11)
C12	0.0443 (14)	0.0475 (14)	0.0411 (12)	0.0034 (12)	−0.0045 (10)	0.0058 (11)
C13	0.0459 (14)	0.0503 (14)	0.0391 (11)	0.0010 (12)	−0.0033 (11)	0.0009 (11)
C14	0.0428 (14)	0.0536 (14)	0.0348 (11)	0.0025 (12)	−0.0047 (10)	−0.0010 (11)
C15	0.0464 (14)	0.0374 (12)	0.0286 (11)	−0.0038 (12)	−0.0052 (10)	−0.0022 (9)
C16	0.0608 (19)	0.101 (2)	0.0509 (15)	0.0196 (19)	0.0077 (14)	0.0040 (16)
N1	0.0404 (10)	0.0512 (12)	0.0317 (9)	0.0005 (10)	−0.0024 (8)	0.0043 (8)
O1	0.0436 (10)	0.0584 (11)	0.0381 (8)	0.0026 (9)	−0.0049 (7)	0.0040 (8)
O2	0.0523 (10)	0.0775 (12)	0.0310 (8)	−0.0123 (10)	−0.0013 (7)	0.0068 (8)
O3	0.0490 (10)	0.0807 (12)	0.0439 (9)	0.0115 (10)	−0.0081 (8)	0.0188 (10)
O4	0.0577 (11)	0.0665 (11)	0.0364 (8)	0.0128 (10)	−0.0014 (8)	0.0083 (8)

C1—C6	1.365 (4)	C10—O3	1.366 (3)
C1—C2	1.386 (4)	C10—C11	1.399 (3)
C1—H1	0.9300	C11—O4	1.365 (3)
C2—C3	1.363 (5)	C11—C12	1.379 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.372 (5)	C13—C14	1.313 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.384 (4)	C14—C15	1.470 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.375 (4)	C15—O1	1.253 (3)
C5—H5	0.9300	C15—O2	1.270 (3)
C6—N1	1.457 (3)	C16—O4	1.418 (3)
C7—C8	1.384 (4)	C16—H16A	0.9600
C7—C12	1.390 (3)	C16—H16B	0.9600
C7—C13	1.475 (3)	C16—H16C	0.9600
C8—C9	1.397 (3)	N1—H1A	0.8900
C8—H8	0.9300	N1—H1B	0.8900
C9—C10	1.381 (3)	N1—H1C	0.8900
C9—H9	0.9300	O3—H3A	0.8200
C6—C1—C2	119.5 (3)	O4—C11—C12	125.8 (2)
C6—C1—H1	120.3	O4—C11—C10	114.18 (19)
C2—C1—H1	120.3	C12—C11—C10	120.1 (2)
C3—C2—C1	120.3 (3)	C11—C12—C7	120.6 (2)
C3—C2—H2	119.8	C11—C12—H12	119.7
C1—C2—H2	119.8	C7—C12—H12	119.7
C2—C3—C4	119.8 (3)	C14—C13—C7	127.8 (2)
C2—C3—H3	120.1	C14—C13—H13	116.1
C4—C3—H3	120.1	C7—C13—H13	116.1
C3—C4—C5	120.6 (3)	C13—C14—C15	123.5 (2)
C3—C4—H4	119.7	C13—C14—H14	118.2
C5—C4—H4	119.7	C15—C14—H14	118.2
C6—C5—C4	118.9 (3)	O1—C15—O2	122.9 (2)
C6—C5—H5	120.6	O1—C15—C14	120.3 (2)
C4—C5—H5	120.6	O2—C15—C14	116.8 (2)
C1—C6—C5	120.9 (2)	O4—C16—H16A	109.5
C1—C6—N1	120.2 (2)	O4—C16—H16B	109.5
C5—C6—N1	118.9 (2)	H16A—C16—H16B	109.5
C8—C7—C12	119.0 (2)	O4—C16—H16C	109.5
C8—C7—C13	123.2 (2)	H16A—C16—H16C	109.5
C12—C7—C13	117.8 (2)	H16B—C16—H16C	109.5
C7—C8—C9	120.9 (2)	C6—N1—H1A	109.5
C7—C8—H8	119.5	C6—N1—H1B	109.5
C9—C8—H8	119.5	H1A—N1—H1B	109.5
C10—C9—C8	119.5 (2)	C6—N1—H1C	109.5
C10—C9—H9	120.3	H1A—N1—H1C	109.5
C8—C9—H9	120.3	H1B—N1—H1C	109.5
O3—C10—C9	118.8 (2)	C10—O3—H3A	109.5
O3—C10—C11	121.4 (2)	C11—O4—C16	117.76 (18)
C9—C10—C11	119.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.89	1.84	2.721 (2)	170
N1—H1B···O1ii	0.89	1.84	2.724 (2)	170
N1—H1C···O2	0.89	1.85	2.730 (3)	170
O3—H3A···O1iii	0.82	2.09	2.841 (2)	151
O3—H3A···O4	0.82	2.25	2.671 (2)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.89	1.84	2.721 (2)	170
N1—H1B⋯O1ii	0.89	1.84	2.724 (2)	170
N1—H1C⋯O2	0.89	1.85	2.730 (3)	170
O3—H3A⋯O1iii	0.82	2.09	2.841 (2)	151
O3—H3A⋯O4	0.82	2.25	2.671 (2)	112

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