4-Phenyl-piperazin-1-ium dihydrogen phosphate.

The title compound, C(10)H(15)N(2) (+)·H(2)PO(4) (-), is built up from 4-phenyl-piperazin-1-ium cations and dihydrogen phosphate anions. The inter-connection between two adjacent anions is assured by two strong O-H⋯O hydrogen bonds, which lead to the formation of infinite wave-like chains which spread along the a axis. The organic cations connect these chains via N-H⋯O hydrogen bonds. The crystal cohesion and stability are ensured by electrostatic and van der Waals inter-actions which, together with N-H⋯O and O-H⋯O hydrogen bonds, build up a two-dimensional network.

Related literature

For the pharmacological properties of phenyl­piperazines and their derivatives, see: Cohen et al. (1982 ▶); Conrado et al. (2008 ▶); Neves et al. (2003 ▶); Hanano et al. (2000 ▶). For related structures, see: Zouari et al. (1995 ▶); Ben Gharbia et al. (2005 ▶). For a discussion of hydrogen bonding, see: Brown (1976 ▶); Blessing (1986 ▶). For tetra­hedral distortions, see: Baur (1974 ▶). For structural discussion, see: Ferraris & Ivaldi (1984 ▶); Janiak (2000 ▶).

Experimental

Crystal data

C10H15N2 +·H2PO4 −

M = 260.23

Orthorhombic,

a = 6.175 (3) Å

b = 8.276 (3) Å

c = 24.408 (9) Å

V = 1247.3 (9) Å3

Z = 4

Ag Kα radiation

λ = 0.56083 Å

μ = 0.12 mm−1

T = 293 K

0.50 × 0.40 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4505 measured reflections

4296 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.029

2 standard reflections every 120 min intensity decay: 6%

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.127

S = 0.94

4296 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 812 Friedel pairs

Flack parameter: −0.1 (2)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030813/dn2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030813/dn2592Isup2.hkl

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

C10H15N2+·H2PO4−	F(000) = 552
Mr = 260.23	Dx = 1.386 Mg m−3
Orthorhombic, P212121	Ag Kα radiation, λ = 0.56083 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.175 (3) Å	θ = 9–11°
b = 8.276 (3) Å	µ = 0.12 mm−1
c = 24.408 (9) Å	T = 293 K
V = 1247.3 (9) Å3	Prism, colourless
Z = 4	0.50 × 0.40 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.029
Radiation source: Enraf Nonius FR590	θmax = 28.0°, θmin = 2.6°
graphite	h = 0→10
non–profiled ω scans	k = 0→13
4505 measured reflections	l = −10→40
4296 independent reflections	2 standard reflections every 120 min
2134 reflections with I > 2σ(I)	intensity decay: 6%

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0539P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
4296 reflections	Δρmax = 0.44 e Å−3
154 parameters	Δρmin = −0.27 e Å−3
0 restraints	Absolute structure: Flack (1983), 812 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.1 (2)

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 > 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	0.9900 (5)	0.0405 (3)	0.07656 (13)	0.0538 (8)
H1C	1.0834	−0.0497	0.0858	0.065*
H1D	0.9118	0.0128	0.0434	0.065*
C2	0.8320 (5)	0.0668 (4)	0.12197 (12)	0.0540 (8)
H2A	0.7262	0.1468	0.1107	0.065*
H2B	0.7557	−0.0333	0.1293	0.065*
C3	1.0653 (6)	0.2676 (3)	0.16155 (12)	0.0529 (7)
H3A	1.1387	0.2996	0.1950	0.063*
H3B	0.9697	0.3549	0.1507	0.063*
C4	1.2291 (5)	0.2386 (4)	0.11736 (13)	0.0525 (8)
H4A	1.3089	0.3375	0.1105	0.063*
H4B	1.3313	0.1570	0.1294	0.063*
C5	0.8136 (4)	0.1192 (3)	0.21995 (12)	0.0413 (6)
C6	0.6143 (5)	0.0404 (4)	0.22358 (14)	0.0516 (8)
H6	0.5592	−0.0117	0.1929	0.062*
C7	0.4984 (6)	0.0382 (4)	0.27123 (16)	0.0647 (10)
H7	0.3657	−0.0149	0.2721	0.078*
C8	0.5724 (7)	0.1121 (4)	0.31782 (16)	0.0705 (10)
H8	0.4907	0.1116	0.3498	0.085*
C9	0.7710 (8)	0.1870 (5)	0.31582 (15)	0.0769 (12)
H9	0.8261	0.2352	0.3473	0.092*
C10	0.8895 (6)	0.1921 (4)	0.26826 (13)	0.0588 (8)
H10	1.0225	0.2448	0.2680	0.071*
N1	1.1243 (4)	0.1849 (3)	0.06624 (10)	0.0396 (5)
H1A	1.2262	0.1615	0.0411	0.047*
H1B	1.0409	0.2649	0.0529	0.047*
N2	0.9374 (4)	0.1210 (2)	0.17176 (9)	0.0406 (5)
P1	0.95373 (11)	0.58755 (7)	0.02154 (3)	0.03303 (15)
O1	1.1831 (3)	0.5806 (2)	0.04795 (8)	0.0458 (5)
H1	1.2422	0.6688	0.0448	0.069*
O2	0.8135 (3)	0.6752 (3)	0.06613 (8)	0.0484 (5)
H2	0.6912	0.6906	0.0542	0.073*
O3	0.8824 (3)	0.4159 (2)	0.01488 (9)	0.0521 (5)
O4	0.9544 (3)	0.6870 (2)	−0.03041 (7)	0.0418 (4)

	U11	U22	U33	U12	U13	U23
C1	0.069 (2)	0.0385 (12)	0.0542 (18)	−0.0065 (13)	0.0118 (16)	−0.0106 (12)
C2	0.0533 (16)	0.0602 (18)	0.0485 (16)	−0.0178 (16)	0.0073 (14)	−0.0121 (15)
C3	0.0628 (17)	0.0529 (15)	0.0428 (15)	−0.0225 (17)	0.0014 (16)	−0.0069 (13)
C4	0.0454 (15)	0.0566 (17)	0.0555 (18)	−0.0096 (14)	−0.0052 (15)	0.0093 (15)
C5	0.0455 (14)	0.0342 (13)	0.0441 (15)	0.0061 (10)	0.0024 (13)	0.0034 (11)
C6	0.0549 (17)	0.0519 (17)	0.0480 (17)	−0.0019 (13)	0.0034 (15)	0.0042 (14)
C7	0.061 (2)	0.066 (2)	0.067 (2)	0.0014 (15)	0.0155 (19)	0.0143 (18)
C8	0.091 (3)	0.0611 (19)	0.059 (2)	0.017 (2)	0.028 (2)	0.0121 (18)
C9	0.123 (4)	0.062 (2)	0.0452 (19)	−0.005 (3)	0.008 (2)	−0.0109 (17)
C10	0.075 (2)	0.0543 (16)	0.0471 (17)	−0.0141 (16)	0.0025 (17)	−0.0121 (15)
N1	0.0432 (11)	0.0319 (9)	0.0436 (12)	0.0102 (9)	0.0062 (11)	0.0050 (10)
N2	0.0445 (11)	0.0364 (10)	0.0410 (12)	−0.0047 (10)	0.0008 (11)	−0.0046 (9)
P1	0.0347 (3)	0.0253 (2)	0.0391 (3)	−0.0019 (3)	−0.0063 (3)	0.0030 (3)
O1	0.0424 (9)	0.0369 (9)	0.0582 (12)	−0.0069 (9)	−0.0132 (9)	0.0143 (9)
O2	0.0507 (11)	0.0541 (11)	0.0403 (10)	0.0097 (10)	0.0004 (9)	0.0037 (9)
O3	0.0599 (10)	0.0271 (7)	0.0693 (13)	−0.0028 (8)	−0.0286 (11)	0.0008 (10)
O4	0.0392 (8)	0.0443 (8)	0.0418 (10)	0.0089 (9)	0.0007 (9)	0.0084 (8)

C1—N1	1.476 (4)	C6—C7	1.366 (5)
C1—C2	1.492 (4)	C6—H6	0.9300
C1—H1C	0.9700	C7—C8	1.370 (6)
C1—H1D	0.9700	C7—H7	0.9300
C2—N2	1.450 (4)	C8—C9	1.375 (6)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—C10	1.373 (5)
C3—N2	1.469 (3)	C9—H9	0.9300
C3—C4	1.498 (5)	C10—H10	0.9300
C3—H3A	0.9700	N1—H1A	0.9000
C3—H3B	0.9700	N1—H1B	0.8998
C4—N1	1.474 (4)	P1—O3	1.496 (2)
C4—H4A	0.9700	P1—O4	1.5114 (19)
C4—H4B	0.9700	P1—O1	1.5572 (19)
C5—C6	1.395 (4)	P1—O2	1.569 (2)
C5—N2	1.403 (4)	O1—H1	0.8197
C5—C10	1.405 (4)	O2—H2	0.8194
N1—C1—C2	112.1 (2)	C6—C7—C8	121.7 (3)
N1—C1—H1C	109.2	C6—C7—H7	119.1
C2—C1—H1C	109.2	C8—C7—H7	119.1
N1—C1—H1D	109.2	C7—C8—C9	118.0 (3)
C2—C1—H1D	109.2	C7—C8—H8	121.0
H1C—C1—H1D	107.9	C9—C8—H8	121.0
N2—C2—C1	112.0 (2)	C10—C9—C8	121.3 (4)
N2—C2—H2A	109.2	C10—C9—H9	119.4
C1—C2—H2A	109.2	C8—C9—H9	119.4
N2—C2—H2B	109.2	C9—C10—C5	121.2 (3)
C1—C2—H2B	109.2	C9—C10—H10	119.4
H2A—C2—H2B	107.9	C5—C10—H10	119.4
N2—C3—C4	110.7 (2)	C4—N1—C1	110.3 (2)
N2—C3—H3A	109.5	C4—N1—H1A	109.6
C4—C3—H3A	109.5	C1—N1—H1A	109.6
N2—C3—H3B	109.5	C4—N1—H1B	109.6
C4—C3—H3B	109.5	C1—N1—H1B	109.6
H3A—C3—H3B	108.1	H1A—N1—H1B	108.2
N1—C4—C3	111.2 (2)	C5—N2—C2	117.0 (2)
N1—C4—H4A	109.4	C5—N2—C3	116.4 (2)
C3—C4—H4A	109.4	C2—N2—C3	110.8 (2)
N1—C4—H4B	109.4	O3—P1—O4	115.26 (11)
C3—C4—H4B	109.4	O3—P1—O1	106.11 (11)
H4A—C4—H4B	108.0	O4—P1—O1	111.40 (11)
C6—C5—N2	122.6 (3)	O3—P1—O2	110.60 (12)
C6—C5—C10	116.2 (3)	O4—P1—O2	109.38 (11)
N2—C5—C10	121.1 (3)	O1—P1—O2	103.41 (12)
C7—C6—C5	121.5 (3)	P1—O1—H1	109.5
C7—C6—H6	119.2	P1—O2—H2	109.5
C5—C6—H6	119.2

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.81	2.587 (3)	158
O2—H2···O4ii	0.82	1.87	2.642 (3)	156
N1—H1B···O3	0.90	1.84	2.731 (3)	171
N1—H1A···O3iii	0.90	1.79	2.675 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.81	2.587 (3)	158
O2—H2⋯O4ii	0.82	1.87	2.642 (3)	156
N1—H1B⋯O3	0.90	1.84	2.731 (3)	171
N1—H1A⋯O3iii	0.90	1.79	2.675 (3)	167

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