Ammonium (E)-3-(4-hy-droxy-3-meth-oxy-phen-yl)prop-2-enoate monohydrate.

In structure of the title compound ammonium ferulate monohydrate, NH(4) (+)·C(10)H(9)O(4) (-)·H(2)O, O-H⋯O and N-H⋯O hydrogen bonds link the ammonium cations, ferulate anions and water mol-ecules into a three-dimensional array. The ferulate anion is approximately planar, with a maximum deviation of 0.307 (2) Å.

Related literature

For the biological activity of ferulic acid, see: Hirabayashi et al. (1995 ▶); Liyama et al. (1994 ▶); Nomura et al. (2003 ▶); Ogiwara et al. (2002 ▶); Ou et al. (2003 ▶).

Experimental

Crystal data

NH4 +·C10H9O4 −·H2O

M = 229.23

Monoclinic,

a = 8.6613 (19) Å

b = 8.3282 (18) Å

c = 16.457 (4) Å

β = 100.525 (3)°

V = 1167.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.30 × 0.27 × 0.26 mm

Data collection

Bruker APEXII diffractometer

5831 measured reflections

2090 independent reflections

1348 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.01

2090 reflections

166 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.18 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/S1600536810042777/gk2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042777/gk2311Isup2.hkl

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

NH4+·C10H9O4−·H2O	F(000) = 488
Mr = 229.23	Dx = 1.305 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1012 reflections
a = 8.6613 (19) Å	θ = 2.5–21.0°
b = 8.3282 (18) Å	µ = 0.11 mm−1
c = 16.457 (4) Å	T = 296 K
β = 100.525 (3)°	Block, colourless
V = 1167.1 (5) Å3	0.30 × 0.27 × 0.26 mm
Z = 4

Bruker APEXII diffractometer	1348 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 25.2°, θmin = 2.5°
φ and ω scan	h = −9→10
5831 measured reflections	k = −9→9
2090 independent reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.106P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2090 reflections	Δρmax = 0.18 e Å−3
166 parameters	Δρmin = −0.18 e Å−3
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

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	0.9208 (2)	−0.0647 (2)	0.33845 (13)	0.0374 (5)
C2	0.9382 (2)	0.0503 (2)	0.27793 (12)	0.0361 (5)
C3	0.8765 (2)	0.2015 (2)	0.28226 (13)	0.0413 (5)
H3	0.8884	0.2782	0.2428	0.050*
C4	0.7969 (2)	0.2398 (3)	0.34519 (14)	0.0432 (6)
H4	0.7547	0.3421	0.3470	0.052*
C5	0.7786 (2)	0.1292 (2)	0.40548 (13)	0.0387 (5)
C6	0.8419 (2)	−0.0247 (2)	0.40114 (13)	0.0402 (5)
H6	0.8306	−0.1007	0.4410	0.048*
C7	0.9605 (3)	−0.3375 (3)	0.38312 (16)	0.0617 (7)
H7A	1.0047	−0.3081	0.4389	0.093*
H7B	1.0094	−0.4342	0.3687	0.093*
H7C	0.8496	−0.3550	0.3785	0.093*
C8	0.6979 (2)	0.1798 (3)	0.47158 (13)	0.0438 (6)
H8	0.6529	0.2815	0.4650	0.053*
C9	0.6790 (2)	0.1034 (3)	0.53912 (13)	0.0438 (6)
H9	0.7113	−0.0031	0.5454	0.053*
C10	0.6093 (3)	0.1780 (3)	0.60560 (14)	0.0413 (5)
O1	0.98669 (18)	−0.21136 (16)	0.32848 (9)	0.0492 (4)
O2	1.01519 (18)	0.00231 (17)	0.21705 (9)	0.0479 (4)
H2	1.0125	0.0744	0.1829	0.072*
O3	0.5464 (2)	0.31626 (18)	0.59297 (9)	0.0557 (5)
O4	0.61918 (18)	0.10581 (17)	0.67298 (9)	0.0503 (4)
N1	0.6808 (3)	0.7821 (2)	0.69610 (14)	0.0506 (5)
H10	0.674 (3)	0.894 (2)	0.6905 (15)	0.076*
H11	0.595 (2)	0.740 (3)	0.7154 (16)	0.076*
H12	0.685 (3)	0.733 (3)	0.6460 (12)	0.076*
H13	0.764 (2)	0.748 (3)	0.7335 (14)	0.076*
O1W	0.3143 (2)	0.3867 (2)	0.45407 (11)	0.0698 (6)
H1W	0.381 (3)	0.358 (3)	0.4970 (14)	0.105*
H2W	0.340 (3)	0.481 (2)	0.4400 (18)	0.105*

	U11	U22	U33	U12	U13	U23
C1	0.0408 (12)	0.0330 (12)	0.0394 (13)	−0.0007 (9)	0.0098 (10)	−0.0022 (9)
C2	0.0411 (12)	0.0403 (12)	0.0302 (12)	−0.0040 (10)	0.0150 (10)	−0.0019 (9)
C3	0.0522 (14)	0.0365 (12)	0.0379 (13)	0.0032 (10)	0.0157 (11)	0.0069 (10)
C4	0.0514 (14)	0.0374 (12)	0.0436 (14)	0.0050 (10)	0.0160 (11)	0.0022 (10)
C5	0.0458 (13)	0.0380 (12)	0.0351 (12)	0.0004 (10)	0.0146 (10)	−0.0029 (10)
C6	0.0506 (13)	0.0395 (12)	0.0325 (12)	−0.0025 (10)	0.0128 (10)	0.0036 (10)
C7	0.0783 (19)	0.0395 (14)	0.0704 (19)	0.0025 (12)	0.0220 (15)	0.0129 (12)
C8	0.0524 (14)	0.0392 (12)	0.0431 (14)	0.0014 (10)	0.0171 (11)	−0.0034 (10)
C9	0.0572 (14)	0.0362 (12)	0.0414 (14)	0.0010 (11)	0.0182 (11)	−0.0016 (10)
C10	0.0491 (14)	0.0399 (13)	0.0374 (13)	−0.0037 (11)	0.0143 (11)	−0.0042 (11)
O1	0.0673 (10)	0.0356 (9)	0.0503 (10)	0.0052 (7)	0.0253 (8)	0.0039 (7)
O2	0.0635 (10)	0.0432 (9)	0.0443 (10)	0.0073 (8)	0.0290 (8)	0.0043 (7)
O3	0.0868 (13)	0.0443 (10)	0.0416 (10)	0.0147 (8)	0.0259 (9)	0.0026 (7)
O4	0.0731 (11)	0.0449 (9)	0.0375 (9)	0.0043 (8)	0.0223 (8)	0.0025 (7)
N1	0.0660 (15)	0.0430 (12)	0.0436 (13)	−0.0077 (11)	0.0120 (11)	0.0037 (10)
O1W	0.0854 (14)	0.0635 (12)	0.0582 (13)	0.0016 (11)	0.0068 (10)	−0.0008 (10)

C1—O1	1.371 (2)	C7—H7C	0.9600
C1—C6	1.378 (3)	C8—C9	1.317 (3)
C1—C2	1.409 (3)	C8—H8	0.9300
C2—O2	1.361 (2)	C9—C10	1.480 (3)
C2—C3	1.375 (3)	C9—H9	0.9300
C3—C4	1.383 (3)	C10—O4	1.250 (2)
C3—H3	0.9300	C10—O3	1.274 (2)
C4—C5	1.384 (3)	O2—H2	0.8200
C4—H4	0.9300	N1—H10	0.942 (17)
C5—C6	1.401 (3)	N1—H11	0.927 (17)
C5—C8	1.458 (3)	N1—H12	0.926 (17)
C6—H6	0.9300	N1—H13	0.903 (17)
C7—O1	1.428 (2)	O1W—H1W	0.863 (16)
C7—H7A	0.9600	O1W—H2W	0.863 (16)
C7—H7B	0.9600
O1—C1—C6	125.42 (19)	O1—C7—H7C	109.5
O1—C1—C2	114.84 (18)	H7A—C7—H7C	109.5
C6—C1—C2	119.74 (19)	H7B—C7—H7C	109.5
O2—C2—C3	123.65 (18)	C9—C8—C5	129.8 (2)
O2—C2—C1	116.80 (18)	C9—C8—H8	115.1
C3—C2—C1	119.54 (18)	C5—C8—H8	115.1
C2—C3—C4	120.12 (19)	C8—C9—C10	123.5 (2)
C2—C3—H3	119.9	C8—C9—H9	118.3
C4—C3—H3	119.9	C10—C9—H9	118.3
C3—C4—C5	121.45 (19)	O4—C10—O3	122.48 (19)
C3—C4—H4	119.3	O4—C10—C9	118.9 (2)
C5—C4—H4	119.3	O3—C10—C9	118.6 (2)
C4—C5—C6	118.34 (19)	C1—O1—C7	117.54 (17)
C4—C5—C8	118.43 (19)	C2—O2—H2	109.5
C6—C5—C8	123.21 (19)	H10—N1—H11	111 (2)
C1—C6—C5	120.79 (19)	H10—N1—H12	111 (2)
C1—C6—H6	119.6	H11—N1—H12	108 (2)
C5—C6—H6	119.6	H10—N1—H13	114 (2)
O1—C7—H7A	109.5	H11—N1—H13	104 (2)
O1—C7—H7B	109.5	H12—N1—H13	108 (2)
H7A—C7—H7B	109.5	H1W—O1W—H2W	108 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O3i	0.86 (2)	2.07 (2)	2.918 (2)	167 (3)
O1W—H1W···O3	0.86 (2)	1.96 (2)	2.817 (2)	173 (3)
N1—H13···O4ii	0.90 (2)	2.06 (2)	2.904 (3)	156 (2)
N1—H12···O1Wi	0.93 (2)	1.93 (2)	2.850 (3)	175 (2)
N1—H11···O1iii	0.93 (2)	2.25 (2)	3.043 (3)	144 (2)
N1—H11···O2iii	0.93 (2)	2.14 (2)	2.823 (2)	130 (2)
N1—H10···O4iv	0.94 (2)	1.83 (2)	2.761 (3)	169 (2)
O2—H2···O3v	0.82	1.81	2.594 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯O3i	0.86 (2)	2.07 (2)	2.918 (2)	167 (3)
O1W—H1W⋯O3	0.86 (2)	1.96 (2)	2.817 (2)	173 (3)
N1—H13⋯O4ii	0.90 (2)	2.06 (2)	2.904 (3)	156 (2)
N1—H12⋯O1Wi	0.93 (2)	1.93 (2)	2.850 (3)	175 (2)
N1—H11⋯O1iii	0.93 (2)	2.25 (2)	3.043 (3)	144 (2)
N1—H11⋯O2iii	0.93 (2)	2.14 (2)	2.823 (2)	130 (2)
N1—H10⋯O4iv	0.94 (2)	1.83 (2)	2.761 (3)	169 (2)
O2—H2⋯O3v	0.82	1.81	2.594 (2)	160

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