4-Acetamido-anilinium nitrate monohydrate.

In the title hydrated salt, C(8)H(11)N(2)O(+)·NO(3) (-)·H(2)O, the N-C bond distances [1.349 (2) and 1.413 (2) Å] along with the sum of the angles (359.88°) around the acetamide N atom clearly indicate that the heteroatom has an sp(2) character. The ammonium group is involved in a total of three N-H⋯O hydrogen bonds, two of these are with a water mol-ecule, which forms two O-H⋯O hydrogen bonds. All these hydrogen bonds link the ionic units and the water mol-ecule into infinite planar layers parallel to (100). The remaining two N-H⋯O inter-actions in which the ammoniun group is involved link these layers into an infinite three-dimensional network.

Related literature

For the structural diversity of <span class="Chemical">amine salts, see: Tooke et al. (2004 ▶). For related <span class="Chemical">nitrate compounds, see: Dai & Chen (2011 ▶); Pourayoubi et al. (2011 ▶); Berrah et al. (2011 ▶). For <span class="Chemical">hydrogen-bond patterns in related compounds, see: Flores-Alamo et al. (2010 ▶). For details of graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8<span class="Species">H11N2O+·<span class="Chemical">NO3 −·H2O

M = 231.21

Monoclinic,

a = 4.1059 (1) Å

b = 23.1112 (5) Å

c = 11.4702 (3) Å

β = 92.942 (1)°

V = 1087.00 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.41 × 0.32 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer

4741 measured reflections

2606 independent reflections

1885 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.142

S = 1.06

2606 reflections

197 parameters

All H-atom parameters refined

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 1997 ▶); cell refinement: DEn class="Chemical">NZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019393/lr2060sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019393/lr2060Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019393/lr2060Isup3.cml

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

C8H11N2O+·NO3−·H2O	F(000) = 488
Mr = 231.21	Dx = 1.413 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4741 reflections
a = 4.1059 (1) Å	θ = 3.0–28.0°
b = 23.1112 (5) Å	µ = 0.12 mm−1
c = 11.4702 (3) Å	T = 295 K
β = 92.942 (1)°	Prismatic, pale yellow
V = 1087.00 (5) Å3	0.41 × 0.32 × 0.25 mm
Z = 4

Nonius KappaCCD diffractometer	1885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 28.0°, θmin = 3.7°
φ scans and ω scans	h = −5→5
4741 measured reflections	k = −30→27
2606 independent reflections	l = −15→15

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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F2) = 0.142	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0773P)2 + 0.1041P] where P = (Fo2 + 2Fc2)/3
2606 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 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
O1	0.1624 (3)	0.11922 (5)	0.45863 (11)	0.0662 (4)
O2	0.6017 (4)	0.36949 (6)	0.53827 (14)	0.0878 (5)
O3	0.3474 (5)	0.30471 (6)	0.63123 (12)	0.0866 (5)
O4	0.3293 (4)	0.30565 (6)	0.44397 (12)	0.0766 (4)
O1W	0.2790 (3)	0.18436 (6)	0.65055 (11)	0.0570 (3)
N1	−0.0860 (3)	0.09798 (5)	0.28298 (12)	0.0500 (3)
N2	0.2062 (4)	−0.13752 (6)	0.21089 (16)	0.0543 (4)
N3	0.4244 (3)	0.32626 (5)	0.53870 (12)	0.0515 (3)
C1	0.0001 (3)	0.03922 (6)	0.27013 (12)	0.0431 (3)
C2	0.1814 (4)	0.00752 (7)	0.35317 (14)	0.0515 (4)
C3	0.2493 (4)	−0.05022 (7)	0.33325 (15)	0.0518 (4)
C4	0.1367 (3)	−0.07607 (6)	0.23129 (13)	0.0447 (3)
C5	−0.0431 (4)	−0.04540 (7)	0.14791 (15)	0.0524 (4)
C6	−0.1123 (4)	0.01213 (7)	0.16734 (14)	0.0519 (4)
C7	−0.0072 (4)	0.13406 (6)	0.37245 (13)	0.0480 (4)
C8	−0.1396 (5)	0.19416 (8)	0.3608 (2)	0.0621 (5)
H1	0.259 (4)	0.0238 (8)	0.4267 (17)	0.061 (5)*
H2	0.369 (5)	−0.0731 (9)	0.3872 (18)	0.065 (5)*
H3	−0.205 (5)	0.1131 (9)	0.2208 (18)	0.060 (5)*
H4	0.374 (5)	−0.1507 (9)	0.2619 (18)	0.067 (5)*
H5	0.243 (6)	−0.1417 (13)	0.135 (3)	0.103 (9)*
H6	0.040 (6)	−0.1603 (12)	0.239 (2)	0.095 (8)*
H7	−0.229 (4)	0.0345 (9)	0.1086 (19)	0.065 (5)*
H8	−0.123 (5)	−0.0614 (9)	0.0796 (18)	0.064 (5)*
H9	−0.251 (9)	0.2023 (17)	0.290 (4)	0.141 (12)*
H10	0.017 (8)	0.2231 (14)	0.371 (3)	0.115 (9)*
H11	−0.272 (8)	0.2008 (15)	0.415 (3)	0.124 (11)*
H1W	0.219 (6)	0.1691 (11)	0.578 (2)	0.087 (7)*
H2W	0.288 (6)	0.2175 (13)	0.639 (2)	0.088 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0952 (9)	0.0479 (7)	0.0534 (7)	0.0049 (6)	−0.0168 (6)	−0.0067 (5)
O2	0.1177 (12)	0.0606 (8)	0.0825 (10)	−0.0398 (8)	−0.0211 (8)	0.0080 (7)
O3	0.1328 (13)	0.0705 (9)	0.0578 (8)	−0.0060 (8)	0.0158 (8)	0.0140 (7)
O4	0.0939 (10)	0.0746 (9)	0.0600 (8)	−0.0196 (7)	−0.0086 (7)	−0.0111 (6)
O1W	0.0760 (8)	0.0460 (7)	0.0485 (7)	−0.0006 (5)	−0.0023 (5)	0.0004 (5)
N1	0.0605 (7)	0.0410 (7)	0.0475 (7)	0.0017 (5)	−0.0055 (6)	−0.0018 (5)
N2	0.0544 (8)	0.0424 (7)	0.0662 (10)	0.0028 (6)	0.0025 (7)	−0.0084 (6)
N3	0.0673 (8)	0.0381 (6)	0.0479 (7)	−0.0029 (5)	−0.0074 (6)	0.0047 (5)
C1	0.0473 (7)	0.0393 (7)	0.0428 (7)	−0.0037 (5)	0.0037 (6)	−0.0003 (6)
C2	0.0631 (9)	0.0466 (8)	0.0438 (8)	0.0018 (7)	−0.0059 (7)	−0.0036 (6)
C3	0.0599 (9)	0.0475 (8)	0.0472 (8)	0.0040 (7)	−0.0039 (7)	0.0018 (7)
C4	0.0451 (7)	0.0393 (7)	0.0505 (8)	−0.0025 (5)	0.0082 (6)	−0.0028 (6)
C5	0.0603 (9)	0.0493 (8)	0.0469 (9)	−0.0030 (7)	−0.0046 (7)	−0.0075 (7)
C6	0.0619 (9)	0.0460 (8)	0.0467 (8)	0.0008 (7)	−0.0074 (7)	0.0005 (7)
C7	0.0531 (8)	0.0422 (8)	0.0487 (8)	−0.0052 (6)	0.0022 (6)	−0.0018 (6)
C8	0.0674 (11)	0.0448 (9)	0.0731 (13)	0.0038 (8)	−0.0067 (10)	−0.0086 (8)

O1—C7	1.2286 (19)	C1—C6	1.393 (2)
O2—N3	1.2363 (18)	C2—C3	1.385 (2)
O3—N3	1.2284 (19)	C2—H1	0.96 (2)
O4—N3	1.2314 (18)	C3—C4	1.372 (2)
O1W—H1W	0.93 (3)	C3—H2	0.93 (2)
O1W—H2W	0.78 (3)	C4—C5	1.375 (2)
N1—C7	1.349 (2)	C5—C6	1.380 (2)
N1—C1	1.4129 (19)	C5—H8	0.91 (2)
N1—H3	0.91 (2)	C6—H7	0.96 (2)
N2—C4	1.4698 (19)	C7—C8	1.495 (2)
N2—H4	0.93 (2)	C8—H9	0.93 (4)
N2—H5	0.89 (3)	C8—H10	0.93 (3)
N2—H6	0.93 (3)	C8—H11	0.86 (4)
C1—C2	1.387 (2)
H1W—O1W—H2W	103 (2)	C4—C3—H2	117.5 (13)
C7—N1—C1	128.48 (14)	C2—C3—H2	122.6 (13)
C7—N1—H3	117.0 (12)	C3—C4—C5	120.93 (14)
C1—N1—H3	114.4 (12)	C3—C4—N2	119.78 (14)
C4—N2—H4	111.1 (13)	C5—C4—N2	119.29 (14)
C4—N2—H5	107.7 (19)	C4—C5—C6	119.47 (15)
H4—N2—H5	115 (2)	C4—C5—H8	123.0 (13)
C4—N2—H6	109.9 (16)	C6—C5—H8	117.5 (13)
H4—N2—H6	97.5 (19)	C5—C6—C1	120.52 (15)
H5—N2—H6	116 (2)	C5—C6—H7	120.4 (12)
O3—N3—O4	121.44 (15)	C1—C6—H7	119.0 (12)
O3—N3—O2	120.58 (15)	O1—C7—N1	122.92 (14)
O4—N3—O2	117.98 (14)	O1—C7—C8	121.34 (15)
C2—C1—C6	119.12 (14)	N1—C7—C8	115.75 (15)
C2—C1—N1	124.34 (14)	C7—C8—H9	115 (2)
C6—C1—N1	116.53 (13)	C7—C8—H10	114.1 (18)
C3—C2—C1	120.07 (15)	H9—C8—H10	106 (3)
C3—C2—H1	117.5 (11)	C7—C8—H11	110 (2)
C1—C2—H1	122.4 (11)	H9—C8—H11	107 (3)
C4—C3—C2	119.89 (15)	H10—C8—H11	104 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1	0.93 (3)	1.79 (3)	2.689 (2)	161 (3)
O1W—H2W···O3	0.78 (3)	2.03 (3)	2.805 (2)	172 (3)
N1—H3···O2i	0.91 (2)	2.24 (2)	3.117 (2)	161 (2)
N2—H4···O1Wii	0.93 (2)	1.87 (2)	2.796 (2)	173 (2)
N2—H5···O2iii	0.89 (3)	2.14 (3)	3.008 (2)	165 (3)
N2—H6···O1Wiv	0.93 (3)	1.95 (2)	2.827 (2)	156 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1	0.93 (3)	1.79 (3)	2.689 (2)	161 (3)
O1W—H2W⋯O3	0.78 (3)	2.03 (3)	2.805 (2)	172 (3)
N1—H3⋯O2i	0.91 (2)	2.24 (2)	3.117 (2)	161 (2)
N2—H4⋯O1Wii	0.93 (2)	1.87 (2)	2.796 (2)	173 (2)
N2—H5⋯O2iii	0.89 (3)	2.14 (3)	3.008 (2)	165 (3)
N2—H6⋯O1Wiv	0.93 (3)	1.95 (2)	2.827 (2)	156 (2)

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