Crystal structure of 2-phenyl-ethyl-amin-ium 4-nitro-phenolate monohydrate.

In the title hydrated mol-ecular salt, C8H12N(+)·C6H4NO3 (-)·H2O, the conformation of the side chain in the cation is anti [C-C-C-N = 179.62 (12)°] and the dihedral angle between the aromatic ring and the nitro group in the anion is 3.34 (11)°. In the crystal, the components are linked by O-H⋯O and N-H⋯O hydrogen bonds, generating (10-1) sheets, which feature R 4 (4)(21) loops. The sheets inter-act by weak aromatic π-π stacking inter-actions [centroid-centroid distance = 3.896 (3) Å], forming a three-dimensional network.

Related literature

For related structures, see: Kanagathara et al. (2012 ▶); Lejon et al. (2006 ▶); Sankar et al. (2014 ▶); Smith et al. (2003 ▶).

Experimental

Crystal data

C8H12N+·C6H4NO3 −·H2O

M = 278.30

Monoclinic,

a = 30.381 (5) Å

b = 6.100 (4) Å

c = 21.357 (5) Å

β = 131.876 (5)°

V = 2947 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.982

14174 measured reflections

3675 independent reflections

2748 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.03

3675 reflections

200 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814025318/hb7318sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814025318/hb7318Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814025318/hb7318Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814025318/hb7318fig1.tif

The mol­ecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

Click here for additional data file.

b . DOI: 10.1107/S1600536814025318/hb7318fig2.tif

The packing of (I), viewed down b axis. Inter­molecular Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

CCDC reference: 1034880

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

C8H12N+·C6H4NO3−·H2O	F(000) = 1184
Mr = 278.30	Dx = 1.254 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 359 reflections
a = 30.381 (5) Å	θ = 1.8–28.4°
b = 6.100 (4) Å	µ = 0.09 mm−1
c = 21.357 (5) Å	T = 295 K
β = 131.876 (5)°	Block, colourless
V = 2947 (2) Å3	0.26 × 0.24 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3675 independent reflections
Radiation source: fine-focus sealed tube	2748 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scan	θmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −38→40
Tmin = 0.976, Tmax = 0.982	k = −7→8
14174 measured reflections	l = −28→28

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) = 0.124	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.954P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3675 reflections	Δρmax = 0.21 e Å−3
200 parameters	Δρmin = −0.19 e Å−3
6 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: 0.0031 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.32367 (5)	0.9073 (2)	0.49756 (8)	0.0480 (3)
C2	0.31910 (8)	1.1138 (3)	0.51903 (11)	0.0709 (4)
H2	0.2885	1.2063	0.4777	0.085*
C3	0.35989 (10)	1.1848 (3)	0.60213 (13)	0.0850 (5)
H3	0.3564	1.3244	0.6159	0.102*
C4	0.40509 (9)	1.0511 (4)	0.66371 (11)	0.0837 (5)
H4	0.4322	1.0990	0.7192	0.100*
C5	0.41005 (7)	0.8477 (4)	0.64310 (10)	0.0770 (5)
H5	0.4407	0.7560	0.6846	0.092*
C6	0.36972 (6)	0.7765 (3)	0.56068 (9)	0.0579 (3)
H6	0.3738	0.6369	0.5476	0.070*
C7	0.28038 (6)	0.8233 (3)	0.40816 (8)	0.0578 (3)
H7A	0.2783	0.9273	0.3719	0.069*
H7B	0.2949	0.6856	0.4052	0.069*
C8	0.21941 (6)	0.7889 (3)	0.37618 (9)	0.0606 (4)
H8A	0.2214	0.6890	0.4133	0.073*
H8B	0.2039	0.9276	0.3763	0.073*
C9	0.12653 (5)	1.0077 (2)	0.10944 (7)	0.0446 (3)
C10	0.10095 (6)	0.8472 (2)	0.04638 (8)	0.0530 (3)
H10	0.1191	0.7110	0.0601	0.064*
C11	0.04981 (6)	0.8868 (2)	−0.03490 (8)	0.0567 (3)
H11	0.0334	0.7782	−0.0756	0.068*
C12	0.02310 (5)	1.0891 (2)	−0.05554 (7)	0.0498 (3)
C13	0.04662 (5)	1.2508 (2)	0.00428 (8)	0.0521 (3)
H13	0.0281	1.3867	−0.0105	0.062*
C14	0.09722 (6)	1.2110 (2)	0.08547 (8)	0.0515 (3)
H14	0.1126	1.3203	0.1257	0.062*
N1	0.17925 (5)	0.6981 (2)	0.28992 (7)	0.0575 (3)
H1A	0.1771 (8)	0.784 (3)	0.2537 (9)	0.081 (5)*
H1B	0.1421 (5)	0.687 (3)	0.2687 (10)	0.079 (5)*
H1C	0.1932 (8)	0.567 (2)	0.2897 (12)	0.087 (6)*
N2	−0.03040 (5)	1.1357 (3)	−0.14047 (8)	0.0693 (4)
O1	0.17576 (4)	0.97214 (16)	0.18676 (5)	0.0576 (3)
O2	−0.05190 (5)	1.3215 (3)	−0.15745 (8)	0.0901 (4)
O3	−0.05367 (6)	0.9919 (3)	−0.19366 (8)	0.1055 (5)
O4	0.23008 (5)	1.3211 (2)	0.29355 (7)	0.0714 (3)
H4A	0.2588 (7)	1.359 (4)	0.2990 (14)	0.107*
H4B	0.2130 (9)	1.221 (3)	0.2576 (11)	0.107*

	U11	U22	U33	U12	U13	U23
C1	0.0467 (6)	0.0555 (7)	0.0463 (6)	−0.0004 (5)	0.0329 (6)	0.0024 (5)
C2	0.0845 (11)	0.0564 (9)	0.0748 (10)	0.0107 (8)	0.0544 (10)	0.0094 (7)
C3	0.1192 (15)	0.0617 (10)	0.0949 (12)	−0.0177 (8)	0.0801 (11)	−0.0224 (8)
C4	0.0833 (11)	0.1073 (15)	0.0598 (9)	−0.0306 (9)	0.0474 (9)	−0.0248 (8)
C5	0.0545 (8)	0.1111 (14)	0.0486 (8)	0.0072 (9)	0.0275 (7)	0.0073 (9)
C6	0.0506 (7)	0.0676 (9)	0.0533 (8)	0.0079 (6)	0.0337 (7)	0.0011 (6)
C7	0.0457 (7)	0.0815 (10)	0.0448 (7)	0.0011 (7)	0.0296 (6)	0.0002 (6)
C8	0.0491 (7)	0.0805 (10)	0.0542 (8)	0.0003 (7)	0.0353 (7)	−0.0014 (7)
C9	0.0342 (5)	0.0487 (7)	0.0426 (6)	−0.0014 (5)	0.0222 (5)	0.0067 (5)
C10	0.0499 (7)	0.0454 (7)	0.0563 (7)	0.0011 (5)	0.0324 (6)	0.0035 (6)
C11	0.0539 (7)	0.0599 (8)	0.0485 (7)	−0.0108 (6)	0.0310 (6)	−0.0067 (6)
C12	0.0355 (5)	0.0668 (8)	0.0396 (6)	−0.0029 (5)	0.0220 (5)	0.0074 (6)
C13	0.0403 (6)	0.0557 (7)	0.0517 (7)	0.0098 (5)	0.0273 (6)	0.0100 (6)
C14	0.0434 (6)	0.0512 (7)	0.0461 (7)	0.0006 (5)	0.0242 (6)	−0.0023 (5)
N1	0.0390 (6)	0.0707 (8)	0.0471 (6)	0.0026 (5)	0.0222 (5)	0.0091 (6)
N2	0.0460 (6)	0.1001 (11)	0.0440 (6)	−0.0063 (7)	0.0227 (6)	0.0111 (7)
O1	0.0395 (5)	0.0603 (6)	0.0456 (5)	0.0021 (4)	0.0170 (4)	0.0098 (4)
O2	0.0524 (6)	0.1087 (10)	0.0654 (7)	0.0168 (6)	0.0211 (6)	0.0326 (7)
O3	0.0852 (9)	0.1324 (13)	0.0444 (6)	−0.0151 (9)	0.0207 (6)	−0.0103 (7)
O4	0.0561 (6)	0.0691 (7)	0.0702 (7)	−0.0085 (5)	0.0344 (6)	−0.0119 (5)

C1—C6	1.3761 (19)	C9—C10	1.4066 (19)
C1—C2	1.379 (2)	C9—C14	1.4084 (19)
C1—C7	1.5116 (18)	C10—C11	1.3729 (19)
C2—C3	1.392 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.378 (2)
C3—C4	1.367 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.377 (2)
C4—C5	1.358 (3)	C12—N2	1.4410 (17)
C4—H4	0.9300	C13—C14	1.3677 (18)
C5—C6	1.382 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	N1—H1A	0.901 (9)
C7—C8	1.5010 (19)	N1—H1B	0.895 (9)
C7—H7A	0.9700	N1—H1C	0.908 (9)
C7—H7B	0.9700	N2—O3	1.220 (2)
C8—N1	1.4795 (19)	N2—O2	1.235 (2)
C8—H8A	0.9700	O4—H4A	0.834 (9)
C8—H8B	0.9700	O4—H4B	0.836 (10)
C9—O1	1.3091 (14)
C6—C1—C2	117.79 (14)	H8A—C8—H8B	108.0
C6—C1—C7	119.94 (13)	O1—C9—C10	121.89 (12)
C2—C1—C7	122.27 (13)	O1—C9—C14	121.15 (12)
C1—C2—C3	120.45 (16)	C10—C9—C14	116.96 (11)
C1—C2—H2	119.8	C11—C10—C9	121.59 (13)
C3—C2—H2	119.8	C11—C10—H10	119.2
C4—C3—C2	120.58 (17)	C9—C10—H10	119.2
C4—C3—H3	119.7	C10—C11—C12	119.33 (13)
C2—C3—H3	119.7	C10—C11—H11	120.3
C5—C4—C3	119.38 (16)	C12—C11—H11	120.3
C5—C4—H4	120.3	C13—C12—C11	120.97 (12)
C3—C4—H4	120.3	C13—C12—N2	118.50 (13)
C4—C5—C6	120.29 (17)	C11—C12—N2	120.53 (13)
C4—C5—H5	119.9	C14—C13—C12	119.79 (13)
C6—C5—H5	119.9	C14—C13—H13	120.1
C1—C6—C5	121.51 (15)	C12—C13—H13	120.1
C1—C6—H6	119.2	C13—C14—C9	121.35 (12)
C5—C6—H6	119.2	C13—C14—H14	119.3
C8—C7—C1	113.03 (10)	C9—C14—H14	119.3
C8—C7—H7A	109.0	C8—N1—H1A	112.1 (12)
C1—C7—H7A	109.0	C8—N1—H1B	111.8 (11)
C8—C7—H7B	109.0	H1A—N1—H1B	105.3 (16)
C1—C7—H7B	109.0	C8—N1—H1C	109.7 (12)
H7A—C7—H7B	107.8	H1A—N1—H1C	106.2 (16)
N1—C8—C7	111.13 (11)	H1B—N1—H1C	111.6 (17)
N1—C8—H8A	109.4	O3—N2—O2	121.46 (14)
C7—C8—H8A	109.4	O3—N2—C12	119.74 (16)
N1—C8—H8B	109.4	O2—N2—C12	118.79 (14)
C7—C8—H8B	109.4	H4A—O4—H4B	106 (2)
C6—C1—C2—C3	−0.3 (2)	C9—C10—C11—C12	0.6 (2)
C7—C1—C2—C3	179.97 (14)	C10—C11—C12—C13	−0.67 (19)
C1—C2—C3—C4	0.0 (3)	C10—C11—C12—N2	179.62 (12)
C2—C3—C4—C5	0.2 (3)	C11—C12—C13—C14	0.01 (19)
C3—C4—C5—C6	−0.1 (3)	N2—C12—C13—C14	179.73 (11)
C2—C1—C6—C5	0.4 (2)	C12—C13—C14—C9	0.8 (2)
C7—C1—C6—C5	−179.87 (13)	O1—C9—C14—C13	178.27 (12)
C4—C5—C6—C1	−0.2 (2)	C10—C9—C14—C13	−0.82 (19)
C6—C1—C7—C8	112.74 (15)	C13—C12—N2—O3	−176.42 (14)
C2—C1—C7—C8	−67.52 (18)	C11—C12—N2—O3	3.3 (2)
C1—C7—C8—N1	−177.62 (13)	C13—C12—N2—O2	3.03 (18)
O1—C9—C10—C11	−178.94 (12)	C11—C12—N2—O2	−177.25 (13)
C14—C9—C10—C11	0.15 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.90 (1)	1.81 (1)	2.7108 (17)	176 (18)
O4—H4B···O1	0.84 (1)	1.90 (1)	2.7262 (18)	173 (2)
N1—H1B···O2i	0.90 (1)	2.11 (1)	2.8937 (17)	145 (15)
N1—H1C···O4ii	0.91 (1)	1.84 (1)	2.742 (2)	172 (18)
O4—H4A···O1iii	0.83 (1)	1.93 (1)	2.7574 (16)	175 (2)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1AO1	0.90(1)	1.81(1)	2.7108(17)	176(18)
O4H4BO1	0.84(1)	1.90(1)	2.7262(18)	173(2)
N1H1BO2i	0.90(1)	2.11(1)	2.8937(17)	145(15)
N1H1CO4ii	0.91(1)	1.84(1)	2.742(2)	172(18)
O4H4AO1iii	0.83(1)	1.93(1)	2.7574(16)	175(2)

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