Piperazin-1-ium 4-amino­benzoate monohydrate

Sivakumar, P.; Mani, A.; Sudhahar, S.; Israel, S.; Chakkaravarthi, G.

doi:10.1107/S2414314616008191

organic compounds

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ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160819

doi:10.1107/S2414314616008191

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Piperazin-1-ium 4-aminobenzoate monohydrate

P. Sivakumar,^a,^b A. Mani,^c S. Sudhahar,^d S. Israel ^e ^* and G. Chakkaravarthi ^b ^*

^aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, India, ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^cDepartment of Physics, Presidency College, Chennai 600 005, India, ^dDepartment of Physics, Alagappa University, Karaikkudi 630 003, India, and ^eDepartment of Physics, The American College, Madurai 625 002, India
^*Correspondence e-mail: , chakkaravarthi_2005@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 17 May 2016; accepted 19 May 2016; online 24 May 2016)

The asymmetric unit of the title hydrated salt, C₄H₁₁N₂⁺·C₇H₆NO₂⁻·H₂O, contains a piperazin-1-ium cation, a 4-aminobenzoate anion and a water molecule. One NH group of the piperazine ring is protonated and this ring adopts a chair conformation. The anion of this salt is generated by deprotonation of the OH group of the carboxylic acid substituent of 4-aminobenzoic acid. The benzene ring makes a dihedral angle of 2.6 (2)° with the carboxylate substituent. The anion and the solvent water molecule are linked by an N—H⋯O hydrogen bond. Additional N—H⋯O and O—H⋯O hydrogen bonds connect adjacent anions through the water molecules, generating a two-dimensional network parallel to (100), forming R₃³(12) ring motifs. Adjacent cations are linked by N—H⋯N hydrogen bonds into infinite chains along (001). These chains are linked to the two-dimensional network of anions and water molecules by another N—H⋯O hydrogen bond, forming a three-dimensional network.

Keywords: crystal structure; molecular salt; hydrogen bonding.

CCDC reference: 1480873

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Chemical scheme

Structure description

In a continuation of our studies of piperazine derivatives, which are known to exhibit anti-bacterial, antimalarial (Chaudhary et al., 2006 ) and antimicrobial (Kharb et al., 2012 ) activity, we report herein the synthesis and crystal structure of the title compound, Fig. 1.

Figure 1
The asymmetric unit of the title molecular salt, showing the atom labelling and 30% probability displacement ellipsoids.

The asymmetric unit contains a piperazin-1-ium cation, a 4-amino benzoate anion and a water molecule. In this organic salt, one NH group of the piperazine ring is protonated while the OH group of the carboxylic acid substituent of 4-amino benzoic acid is deprotonated. The bond lengths are in normal ranges and comparable to those found in a related structure (Wei, 2011 ). The piperazinium ring adopts a chair conformation, with puckering parameters Q = 0.547 (3) Å, θ = 180.0 (3), ψ = 23 (3)°. The C1–C6 benzene ring in the anion subtends a dihedral angle of 2.6 (2)° to the carboxylate (O1/C7/O2) substituent.

In the asymmetric unit, the anion and water molecule are linked via an intermolecular N1—H1B⋯O3 hydrogen bond. Additional N—H⋯O and O—H⋯O hydrogen bonds, Table 1, connect the anions through water molecules into a two-dimensional network parallel to (100) and generates an R₃³(12) ring motif, Fig. 2. The cations are linked by an N—H⋯N hydrogen bond into infinite chains along (001). These cation chains are also linked to the two-dimensional network of anions and water molecules by an N3—H3B⋯O1 hydrogen bond, forming a three-dimensional network, Fig. 3.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O3	0.86	2.19	3.027 (3)	165
N1—H1A⋯O2ⁱ	0.86	2.12	2.962 (2)	168
N2—H2A⋯N1ⁱⁱ	0.88 (1)	2.57 (2)	3.335 (3)	147 (2)
N3—H3A⋯N2ⁱⁱⁱ	0.90	1.92	2.793 (2)	165
N3—H3B⋯O1^iv	0.90	1.84	2.726 (2)	166
O3—H3C⋯O2^v	0.83 (1)	1.91 (1)	2.737 (2)	176 (4)
O3—H3D⋯O1^vi	0.83 (1)	1.95 (1)	2.776 (2)	177 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (iii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iv) x, y-1, z; (v) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (vi) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
A partial view of the crystal packing, showing the R₃³(12) ring motif. The hydrogen bonds are shown as dashed lines (see Table 1

) and C-bound H atoms have been omitted for clarity.

Figure 3
The crystal packing of the title compound, viewed along the b axis.

Synthesis and crystallization

The title compound was synthesized from 4-amino-benzoic acid (1.828 g) and piperazine (1.148 g) in an equimolar ratio. The reactants were dissolved in 10 ml of acetone and the solvent was allowed to slowly evaporate at room temperature. After one week, crystals suitable for X-ray diffraction were obtained.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₄H₁₁N₂⁺·C₇H₆NO₂⁻·H₂O
M_r	241.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	18.2964 (14), 7.1388 (6), 10.3574 (6)
V (Å³)	1352.83 (17)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.976, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	15633, 2648, 1981
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.091, 1.06
No. of reflections	2648
No. of parameters	167
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.12
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1480873

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616008191/sj4036sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616008191/sj4036Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616008191/sj4036Isup3.cml

checkCIF report

Synthesis and crystallization top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1

Experimental top

Structure description top

In a continuation of our studies of piperazine derivatives, which are known to exhibit anti-bacterial, antimalarial (Chaudhary et al., 2006) and antimicrobial (Kharb et al., 2012) activity, we report herein the synthesis and crystal structure of the title compound, Fig. 1.

The asymmetric unit contains a piperazin-1-ium cation, a 4-amino benzoate anion and a water molecule. In this organic salt, one NH group of the piperazinium ring is protonated while the OH group of the carboxylic acid substituent of 4-amino benzoic acid is deprotonated. The bond lengths are in normal ranges and comparable to those found in a related structure (Wei, 2011). The piperazinium ring adopts a chair conformation, with puckering parameters Q = 0.547 (3) Å, θ = 180.0 (3), ψ = 23 (3)°. The C1–C6 benzene ring in the anion subtends a dihedral angle of 2.6 (2)° to the carboxylate (O1/C7/O2) substituent.

In the asymmetric unit, the anion and water molecule are linked via an intermolecular N1—H1B···O3 hydrogen bond. Additional N—H···O and O—H···O hydrogen bonds, Table 1, connect the anions through water molecules into a two-dimensional network parallel to (100) and generates an R₃³(12) ring motif, Fig. 2. The cations are linked by an N—H···N hydrogen bond into infinite chains along (001). These cation chains are also linked to the two-dimensional network of anions and water molecules by an N3—H3B···O1 hydrogen bond, forming a three-dimensional network, Fig. 3.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title molecular salt, showing the atom labelling and 30% probability displacement ellipsoids.
	Fig. 2. A partial view of the crystal packing, showing the R₃³(12) ring motif. The hydrogen bonds are shown as dashed lines (see Table 1) and C-bound H atoms have been omitted for clarity.
	Fig. 3. The crystal packing of the title compound, viewed along the b axis.

Piperazin-1-ium 4-aminobenzoate monohydrate top

Crystal data top

C₄H₁₁N₂⁺·C₇H₆NO₂⁻·H₂O	F(000) = 520
M_r = 241.29	D_x = 1.185 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5261 reflections
a = 18.2964 (14) Å	θ = 2.2–25.9°
b = 7.1388 (6) Å	µ = 0.09 mm⁻¹
c = 10.3574 (6) Å	T = 295 K
V = 1352.83 (17) Å³	Block, colourless
Z = 4	0.28 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2648 independent reflections
Radiation source: fine-focus sealed tube	1981 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω and φ scan	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −22→22
T_min = 0.976, T_max = 0.983	k = −8→8
15633 measured reflections	l = −12→12

Refinement top

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0381P)² + 0.1919P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2648 reflections	Δρ_max = 0.12 e Å⁻³
167 parameters	Δρ_min = −0.12 e Å⁻³
5 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: 0.0150 (17)

Crystal data top

C₄H₁₁N₂⁺·C₇H₆NO₂⁻·H₂O	V = 1352.83 (17) Å³
M_r = 241.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 18.2964 (14) Å	µ = 0.09 mm⁻¹
b = 7.1388 (6) Å	T = 295 K
c = 10.3574 (6) Å	0.28 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2648 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1981 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.983	R_int = 0.039
15633 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	5 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.12 e Å⁻³
2648 reflections	Δρ_min = −0.12 e Å⁻³
167 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.68490 (11)	0.8943 (3)	0.39677 (18)	0.0397 (5)
C2	0.72877 (11)	0.8264 (3)	0.49587 (19)	0.0456 (5)
H2	0.7151	0.8482	0.5811	0.055*
C3	0.79165 (12)	0.7279 (3)	0.4713 (2)	0.0498 (6)
H3	0.8200	0.6843	0.5395	0.060*
C4	0.81335 (11)	0.6927 (3)	0.34408 (19)	0.0443 (5)
C5	0.77022 (11)	0.7605 (3)	0.24516 (19)	0.0468 (5)
H5	0.7837	0.7387	0.1599	0.056*
C6	0.70757 (11)	0.8600 (3)	0.27110 (19)	0.0431 (5)
H6	0.6797	0.9053	0.2028	0.052*
C7	0.61580 (11)	0.9950 (3)	0.4256 (2)	0.0421 (5)
C8	0.43405 (14)	0.4288 (4)	0.2356 (2)	0.0613 (7)
H8A	0.4465	0.3101	0.1958	0.074*
H8B	0.3846	0.4606	0.2097	0.074*
C9	0.43638 (14)	0.4070 (4)	0.3798 (2)	0.0588 (7)
H9A	0.4188	0.5208	0.4206	0.071*
H9B	0.4047	0.3048	0.4058	0.071*
C10	0.56413 (18)	0.5115 (4)	0.3763 (2)	0.0717 (8)
H10A	0.6136	0.4750	0.3989	0.086*
H10B	0.5537	0.6305	0.4175	0.086*
C11	0.55779 (16)	0.5321 (4)	0.2312 (3)	0.0713 (8)
H11A	0.5898	0.6323	0.2029	0.086*
H11B	0.5742	0.4172	0.1904	0.086*
N1	0.87752 (10)	0.5984 (3)	0.31881 (19)	0.0653 (6)
H1A	0.8913	0.5809	0.2404	0.078*
H1B	0.9038	0.5570	0.3815	0.078*
N2	0.48383 (14)	0.5724 (3)	0.18885 (18)	0.0634 (6)
N3	0.51219 (11)	0.3684 (3)	0.42236 (16)	0.0506 (5)
H3A	0.5135	0.3644	0.5092	0.061*
H3B	0.5260	0.2554	0.3925	0.061*
O1	0.57619 (8)	1.0491 (2)	0.33263 (13)	0.0584 (4)
O2	0.59834 (8)	1.0228 (3)	0.54085 (13)	0.0615 (5)
O3	0.94991 (10)	0.4935 (3)	0.57142 (17)	0.0714 (5)
H2A	0.4749 (15)	0.677 (2)	0.231 (2)	0.083 (10)*
H3C	0.9945 (6)	0.492 (5)	0.560 (4)	0.109 (12)*
H3D	0.9410 (16)	0.508 (4)	0.6489 (12)	0.084 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0390 (11)	0.0435 (12)	0.0365 (11)	−0.0028 (10)	0.0000 (9)	−0.0025 (9)
C2	0.0447 (12)	0.0605 (14)	0.0315 (11)	0.0010 (11)	0.0013 (9)	−0.0008 (10)
C3	0.0497 (13)	0.0617 (16)	0.0380 (11)	0.0075 (12)	−0.0032 (10)	0.0070 (10)
C4	0.0435 (12)	0.0434 (13)	0.0459 (12)	0.0040 (10)	0.0021 (10)	0.0007 (10)
C5	0.0494 (12)	0.0581 (15)	0.0329 (10)	0.0028 (12)	0.0040 (9)	−0.0011 (10)
C6	0.0413 (11)	0.0540 (15)	0.0341 (11)	−0.0007 (11)	−0.0039 (9)	0.0019 (9)
C7	0.0370 (12)	0.0505 (13)	0.0387 (11)	−0.0024 (10)	−0.0021 (9)	−0.0057 (10)
C8	0.0640 (15)	0.0687 (18)	0.0510 (14)	0.0107 (13)	−0.0036 (12)	0.0046 (12)
C9	0.0678 (16)	0.0578 (16)	0.0509 (13)	0.0121 (13)	0.0104 (11)	0.0066 (12)
C10	0.093 (2)	0.0741 (19)	0.0479 (14)	−0.0296 (16)	−0.0116 (13)	0.0068 (13)
C11	0.088 (2)	0.076 (2)	0.0495 (15)	−0.0304 (16)	0.0042 (14)	0.0085 (13)
N1	0.0639 (13)	0.0832 (15)	0.0486 (11)	0.0303 (12)	0.0019 (10)	0.0007 (11)
N2	0.1045 (18)	0.0488 (13)	0.0371 (10)	0.0057 (13)	0.0009 (11)	0.0033 (10)
N3	0.0736 (13)	0.0448 (10)	0.0335 (9)	0.0042 (10)	−0.0001 (9)	0.0006 (8)
O1	0.0590 (9)	0.0783 (12)	0.0379 (8)	0.0226 (8)	−0.0080 (8)	−0.0100 (8)
O2	0.0460 (8)	0.1006 (13)	0.0378 (9)	0.0128 (9)	0.0010 (7)	−0.0088 (8)
O3	0.0476 (11)	0.1231 (16)	0.0434 (10)	0.0115 (11)	−0.0006 (8)	−0.0115 (10)

Geometric parameters (Å, º) top

C1—C6	1.388 (3)	C9—N3	1.481 (3)
C1—C2	1.390 (3)	C9—H9A	0.9700
C1—C7	1.485 (3)	C9—H9B	0.9700
C2—C3	1.372 (3)	C10—N3	1.475 (3)
C2—H2	0.9300	C10—C11	1.514 (3)
C3—C4	1.399 (3)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—N1	1.379 (3)	C11—N2	1.451 (4)
C4—C5	1.381 (3)	C11—H11A	0.9700
C5—C6	1.375 (3)	C11—H11B	0.9700
C5—H5	0.9300	N1—H1A	0.8600
C6—H6	0.9300	N1—H1B	0.8600
C7—O2	1.252 (2)	N2—H2A	0.878 (10)
C7—O1	1.265 (2)	N3—H3A	0.9000
C8—N2	1.454 (3)	N3—H3B	0.9000
C8—C9	1.502 (3)	O3—H3C	0.825 (10)
C8—H8A	0.9700	O3—H3D	0.825 (10)
C8—H8B	0.9700

C6—C1—C2	117.26 (18)	C8—C9—H9A	109.7
C6—C1—C7	121.92 (17)	N3—C9—H9B	109.7
C2—C1—C7	120.80 (17)	C8—C9—H9B	109.7
C3—C2—C1	121.72 (18)	H9A—C9—H9B	108.2
C3—C2—H2	119.1	N3—C10—C11	109.8 (2)
C1—C2—H2	119.1	N3—C10—H10A	109.7
C2—C3—C4	120.33 (19)	C11—C10—H10A	109.7
C2—C3—H3	119.8	N3—C10—H10B	109.7
C4—C3—H3	119.8	C11—C10—H10B	109.7
N1—C4—C5	121.14 (18)	H10A—C10—H10B	108.2
N1—C4—C3	120.55 (19)	N2—C11—C10	113.0 (2)
C5—C4—C3	118.28 (18)	N2—C11—H11A	109.0
C6—C5—C4	120.83 (17)	C10—C11—H11A	109.0
C6—C5—H5	119.6	N2—C11—H11B	109.0
C4—C5—H5	119.6	C10—C11—H11B	109.0
C5—C6—C1	121.59 (18)	H11A—C11—H11B	107.8
C5—C6—H6	119.2	C4—N1—H1A	120.0
C1—C6—H6	119.2	C4—N1—H1B	120.0
O2—C7—O1	122.08 (19)	H1A—N1—H1B	120.0
O2—C7—C1	119.08 (18)	C11—N2—C8	110.1 (2)
O1—C7—C1	118.84 (18)	C11—N2—H2A	101.1 (19)
N2—C8—C9	112.7 (2)	C8—N2—H2A	108.4 (19)
N2—C8—H8A	109.0	C10—N3—C9	112.22 (19)
C9—C8—H8A	109.0	C10—N3—H3A	109.2
N2—C8—H8B	109.0	C9—N3—H3A	109.2
C9—C8—H8B	109.0	C10—N3—H3B	109.2
H8A—C8—H8B	107.8	C9—N3—H3B	109.2
N3—C9—C8	109.97 (19)	H3A—N3—H3B	107.9
N3—C9—H9A	109.7	H3C—O3—H3D	110 (3)

C6—C1—C2—C3	−0.5 (3)	C6—C1—C7—O2	−179.6 (2)
C7—C1—C2—C3	177.9 (2)	C2—C1—C7—O2	2.0 (3)
C1—C2—C3—C4	−0.1 (3)	C6—C1—C7—O1	0.8 (3)
C2—C3—C4—N1	178.2 (2)	C2—C1—C7—O1	−177.6 (2)
C2—C3—C4—C5	0.4 (3)	N2—C8—C9—N3	−55.7 (3)
N1—C4—C5—C6	−177.8 (2)	N3—C10—C11—N2	54.9 (3)
C3—C4—C5—C6	0.0 (3)	C10—C11—N2—C8	−55.8 (3)
C4—C5—C6—C1	−0.7 (3)	C9—C8—N2—C11	56.3 (3)
C2—C1—C6—C5	0.9 (3)	C11—C10—N3—C9	−53.9 (3)
C7—C1—C6—C5	−177.5 (2)	C8—C9—N3—C10	54.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3	0.86	2.19	3.027 (3)	165
N1—H1A···O2ⁱ	0.86	2.12	2.962 (2)	168
N2—H2A···N1ⁱⁱ	0.88 (1)	2.57 (2)	3.335 (3)	147 (2)
N3—H3A···N2ⁱⁱⁱ	0.90	1.92	2.793 (2)	165
N3—H3B···O1^iv	0.90	1.84	2.726 (2)	166
O3—H3C···O2^v	0.83 (1)	1.91 (1)	2.737 (2)	176 (4)
O3—H3D···O1^vi	0.83 (1)	1.95 (1)	2.776 (2)	177 (3)

Symmetry codes: (i) −x+3/2, y−1/2, z−1/2; (ii) x−1/2, −y+3/2, z; (iii) −x+1, −y+1, z+1/2; (iv) x, y−1, z; (v) x+1/2, −y+3/2, z; (vi) −x+3/2, y−1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3	0.86	2.19	3.027 (3)	165
N1—H1A···O2ⁱ	0.86	2.12	2.962 (2)	168
N2—H2A···N1ⁱⁱ	0.878 (10)	2.565 (17)	3.335 (3)	147 (2)
N3—H3A···N2ⁱⁱⁱ	0.90	1.92	2.793 (2)	165
N3—H3B···O1^iv	0.90	1.84	2.726 (2)	166
O3—H3C···O2^v	0.825 (10)	1.912 (11)	2.737 (2)	176 (4)
O3—H3D···O1^vi	0.825 (10)	1.951 (10)	2.776 (2)	177 (3)

Symmetry codes: (i) −x+3/2, y−1/2, z−1/2; (ii) x−1/2, −y+3/2, z; (iii) −x+1, −y+1, z+1/2; (iv) x, y−1, z; (v) x+1/2, −y+3/2, z; (vi) −x+3/2, y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₄H₁₁N₂⁺·C₇H₆NO₂⁻·H₂O
M_r	241.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	18.2964 (14), 7.1388 (6), 10.3574 (6)
V (Å³)	1352.83 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.976, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	15633, 2648, 1981
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.091, 1.06
No. of reflections	2648
No. of parameters	167
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.12

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chaudhary, P., Kumar, R., Verma, K., Singh, D., Yadav, V., Chhillar, A. K., Sharma, G. L. & Chandra, R. (2006). Bioorg. Med. Chem. 14, 1819–1826. CrossRef PubMed CAS Google Scholar
Kharb, R., Bansal, K. & Sharma, A. K. (2012). Pharma Chem. 4, 2470–2488. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, B. (2011). Acta Cryst. E67, o2811. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 1| Part 5| May 2016| x160819

doi:10.1107/S2414314616008191

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Piperazin-1-ium 4-amino­benzoate monohydrate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

Piperazin-1-ium 4-aminobenzoate monohydrate