4-(4-Carboxy­benz­yl)-1-methyl­piperazin-1-ium picrate

Li, H.; Hakim Al-arique, Q.N.M.; Yathirajan, H.S.; Narayana, B.; Ramesha, A.R.

doi:10.1107/S1600536809004474

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o518

doi:10.1107/S1600536809004474

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4-(4-Carboxybenzyl)-1-methylpiperazin-1-ium picrate

Hongqi Li,^a ^* Q. N. M. Hakim Al-arique,^b H. S. Yathirajan,^b B. Narayana ^c and A. R. Ramesha ^d

^aKey Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dRL Fine Chem, Bangalore 560 064, India
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 27 December 2008; accepted 7 February 2009; online 13 February 2009)

The title compound, C₁₃H₁₉N₂O₂⁺·C₆H₂N₃O₇⁻, is a salt obtained by cocrystallization of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid and picric acid. The cations adopt an `L-shaped' conformation and are linked into chains along [010] by O—H⋯N hydrogen bonds. The NH group of each piperazinium ring forms a hydrogen bond to the phenolate O atom of a picrate anion, and the picrate anions form face-to-face contacts with an interplanar separation of 3.023 (1) Å.

Related literature

For general background, see: Druker et al. (2001 ). For related structures, see: Swamy et al. (2007 ); Bindya et al. (2007 ); Sarojini et al. (2007 ); Wang & Jia (2008 ).

Experimental

Crystal data

C₁₃H₁₉N₂O₂⁺·C₆H₂N₃O₇⁻
M_r = 463.41
Triclinic, $[P \overline 1]$
a = 7.3020 (12) Å
b = 9.5993 (16) Å
c = 15.131 (3) Å
α = 86.448 (2)°
β = 79.145 (2)°
γ = 79.950 (2)°
V = 1025.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.965, T_max = 0.976
5373 measured reflections
3565 independent reflections
2745 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.06
3565 reflections
305 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯N4ⁱ	0.82	1.79	2.6006 (19)	172
N5—H5A⋯O1ⁱⁱ	0.89 (2)	1.89 (2)	2.734 (2)	156.9 (18)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004474/bi2341sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004474/bi2341Isup2.hkl

checkCIF report

Comment top

4-[(4-Methylpiperazin-1-yl)methyl]benzoic acid is an intermediate in the synthesis of Imatinib, a drug used to treat certain types of cancer. Its mesylate salt is currently marketed by Novartis as Gleevec (Druker et al., 2001). Picric acid forms salts or charge-transfer complexes with many organic compounds. Crystal structures of picrate complexes with organic compounds of pharmaceutical importance viz., desipraminium picrate (Swamy et al., 2007) and amitriptylinium picrate (Bindya et al., 2007) have been reported. A three-dimensional network in piperazine-1,4-diium-picrate-piperazine (1/2/1) is reported recently (Wang & Jia, 2008).

Related literature top

For general background, see: Druker et al. (2001). For related structures, see: Swamy et al. (2007); Bindya et al. (2007); Sarojini et al. (2007); Wang & Jia (2008).

Experimental top

The title compound was prepared by taking equimolar quantities of picric acid (0.92 g, 2 mmol) and 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid (0.47 g, 2 mmol) and dissolving them in water. The solution was stirred well at room temperature and slow evaporation of the solution resulted in the formation of the yellow coloured salt (yield 95%). Crystals suitable for single-crystal X-ray diffraction were grown from dimethyl formamide solvent.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure with displacement ellipsoids drawn at the 30% probability level for non-H atoms.

4-(4-Carboxybenzyl)-1-methylpiperazin-1-ium picrate top

Crystal data top

C₁₃H₁₉N₂O₂⁺·C₆H₂N₃O₇⁻	Z = 2
M_r = 463.41	F(000) = 484
Triclinic, P1	D_x = 1.501 Mg m⁻³
Hall symbol: -P 1	Melting point = 510–504 K
a = 7.3020 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5993 (16) Å	Cell parameters from 1962 reflections
c = 15.131 (3) Å	θ = 2.5–26.9°
α = 86.448 (2)°	µ = 0.12 mm⁻¹
β = 79.145 (2)°	T = 296 K
γ = 79.950 (2)°	Block, colourless
V = 1025.2 (3) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	3565 independent reflections
Radiation source: fine-focus sealed tube	2745 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→6
T_min = 0.965, T_max = 0.976	k = −11→9
5373 measured reflections	l = −18→18

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0447P)² + 0.2218P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3565 reflections	Δρ_max = 0.18 e Å⁻³
305 parameters	Δρ_min = −0.17 e Å⁻³
0 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: 0.023 (2)

Crystal data top

C₁₃H₁₉N₂O₂⁺·C₆H₂N₃O₇⁻	γ = 79.950 (2)°
M_r = 463.41	V = 1025.2 (3) Å³
Triclinic, P1	Z = 2
a = 7.3020 (12) Å	Mo Kα radiation
b = 9.5993 (16) Å	µ = 0.12 mm⁻¹
c = 15.131 (3) Å	T = 296 K
α = 86.448 (2)°	0.30 × 0.20 × 0.20 mm
β = 79.145 (2)°

Data collection top

Bruker SMART CCD diffractometer	3565 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2745 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.976	R_int = 0.016
5373 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.18 e Å⁻³
3565 reflections	Δρ_min = −0.17 e Å⁻³
305 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.5333 (3)	1.0778 (2)	0.14228 (14)	0.0426 (5)
C2	0.6431 (3)	1.0691 (2)	0.05175 (13)	0.0438 (5)
C3	0.7751 (3)	0.9547 (2)	0.02127 (13)	0.0430 (5)
H3	0.8395	0.9546	−0.0379	0.052*
C4	0.8126 (3)	0.8398 (2)	0.07793 (12)	0.0379 (4)
C5	0.7175 (2)	0.83776 (19)	0.16598 (12)	0.0359 (4)
H5	0.7422	0.7595	0.2039	0.043*
C6	0.5870 (3)	0.9521 (2)	0.19627 (12)	0.0372 (4)
C7	0.1636 (3)	1.33630 (19)	0.60024 (12)	0.0366 (4)
C8	0.1280 (2)	1.18702 (18)	0.60753 (11)	0.0320 (4)
C9	0.2178 (3)	1.09572 (19)	0.53938 (12)	0.0380 (4)
H9	0.2943	1.1292	0.4892	0.046*
C10	0.1949 (3)	0.95535 (19)	0.54527 (12)	0.0391 (4)
H10	0.2557	0.8954	0.4989	0.047*
C11	0.0818 (2)	0.90303 (18)	0.61993 (12)	0.0349 (4)
C12	−0.0108 (2)	0.99528 (18)	0.68722 (12)	0.0361 (4)
H12	−0.0897	0.9622	0.7367	0.043*
C13	0.0123 (2)	1.13606 (18)	0.68187 (12)	0.0348 (4)
H13	−0.0494	1.1964	0.7279	0.042*
C14	0.0608 (3)	0.74891 (19)	0.62770 (13)	0.0413 (5)
H14A	−0.0640	0.7413	0.6616	0.050*
H14B	0.0677	0.7156	0.5677	0.050*
C15	0.3984 (3)	0.6541 (2)	0.62183 (12)	0.0399 (5)
H15A	0.4281	0.7488	0.6208	0.048*
H15B	0.4063	0.6282	0.5601	0.048*
C16	0.5410 (3)	0.5522 (2)	0.66450 (12)	0.0415 (5)
H16A	0.5196	0.4562	0.6598	0.050*
H16B	0.6674	0.5591	0.6324	0.050*
C17	0.3292 (3)	0.5816 (2)	0.80965 (12)	0.0402 (5)
H17A	0.3189	0.6046	0.8721	0.048*
H17B	0.2985	0.4875	0.8083	0.048*
C18	0.1914 (3)	0.68674 (19)	0.76667 (12)	0.0375 (4)
H18A	0.0639	0.6846	0.7991	0.045*
H18B	0.2190	0.7813	0.7701	0.045*
C19	0.6653 (3)	0.4834 (2)	0.80485 (15)	0.0598 (6)
H19A	0.6595	0.5121	0.8651	0.090*
H19B	0.7903	0.4841	0.7710	0.090*
H19C	0.6355	0.3896	0.8065	0.090*
N1	0.6141 (3)	1.1856 (2)	−0.01420 (15)	0.0587 (5)
N2	0.9524 (2)	0.71935 (19)	0.04516 (11)	0.0471 (4)
N3	0.4925 (2)	0.9427 (2)	0.28970 (11)	0.0469 (4)
N4	0.2038 (2)	0.65332 (14)	0.67160 (9)	0.0340 (4)
N5	0.5264 (2)	0.58329 (17)	0.76126 (10)	0.0375 (4)
O1	0.4059 (2)	1.17657 (15)	0.17135 (11)	0.0614 (4)
O2	0.5114 (3)	1.2956 (2)	0.00975 (14)	0.0921 (6)
O3	0.6952 (3)	1.16659 (19)	−0.09220 (12)	0.0799 (6)
O4	1.0379 (2)	0.72647 (18)	−0.03240 (10)	0.0680 (5)
O5	0.9804 (2)	0.61680 (16)	0.09632 (11)	0.0649 (5)
O6	0.4639 (2)	0.82634 (18)	0.32167 (10)	0.0633 (4)
O7	0.4470 (2)	1.05126 (19)	0.33248 (10)	0.0707 (5)
O8	0.1067 (2)	1.40458 (13)	0.67570 (8)	0.0445 (4)
H8	0.1397	1.4825	0.6691	0.067*
O9	0.2400 (2)	1.38891 (15)	0.53152 (9)	0.0605 (4)
H5A	0.551 (3)	0.669 (2)	0.7674 (13)	0.045 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0386 (11)	0.0359 (11)	0.0586 (13)	−0.0106 (8)	−0.0166 (9)	−0.0054 (9)
C2	0.0462 (12)	0.0407 (11)	0.0508 (12)	−0.0163 (9)	−0.0195 (10)	0.0092 (9)
C3	0.0449 (11)	0.0537 (13)	0.0350 (10)	−0.0208 (10)	−0.0079 (9)	0.0021 (9)
C4	0.0359 (10)	0.0421 (11)	0.0355 (10)	−0.0087 (8)	−0.0032 (8)	−0.0036 (8)
C5	0.0377 (10)	0.0382 (10)	0.0345 (10)	−0.0097 (8)	−0.0102 (8)	−0.0007 (8)
C6	0.0368 (10)	0.0426 (11)	0.0348 (10)	−0.0100 (8)	−0.0079 (8)	−0.0059 (8)
C7	0.0393 (10)	0.0345 (10)	0.0353 (10)	−0.0079 (8)	−0.0036 (8)	−0.0002 (8)
C8	0.0339 (9)	0.0298 (9)	0.0334 (9)	−0.0060 (7)	−0.0086 (8)	−0.0001 (7)
C9	0.0457 (11)	0.0366 (10)	0.0307 (9)	−0.0071 (8)	−0.0045 (8)	0.0000 (8)
C10	0.0491 (11)	0.0327 (10)	0.0349 (10)	−0.0028 (8)	−0.0081 (9)	−0.0067 (8)
C11	0.0360 (10)	0.0296 (10)	0.0423 (10)	−0.0070 (7)	−0.0141 (8)	0.0004 (8)
C12	0.0311 (10)	0.0339 (10)	0.0415 (10)	−0.0064 (7)	−0.0026 (8)	0.0042 (8)
C13	0.0327 (9)	0.0311 (10)	0.0378 (10)	−0.0029 (7)	−0.0008 (8)	−0.0027 (8)
C14	0.0461 (11)	0.0317 (10)	0.0503 (11)	−0.0104 (8)	−0.0157 (9)	−0.0015 (8)
C15	0.0448 (11)	0.0371 (10)	0.0347 (10)	−0.0087 (8)	0.0013 (8)	0.0020 (8)
C16	0.0423 (11)	0.0371 (11)	0.0385 (10)	−0.0016 (8)	0.0047 (8)	−0.0018 (8)
C17	0.0392 (10)	0.0418 (11)	0.0348 (10)	−0.0040 (8)	0.0030 (8)	−0.0016 (8)
C18	0.0349 (10)	0.0371 (10)	0.0380 (10)	−0.0026 (8)	−0.0013 (8)	−0.0070 (8)
C19	0.0513 (13)	0.0579 (14)	0.0596 (14)	0.0144 (11)	−0.0087 (11)	0.0092 (11)
N1	0.0678 (13)	0.0507 (12)	0.0688 (14)	−0.0265 (10)	−0.0316 (11)	0.0184 (10)
N2	0.0420 (10)	0.0529 (11)	0.0439 (10)	−0.0091 (8)	0.0012 (8)	−0.0076 (8)
N3	0.0368 (9)	0.0614 (12)	0.0420 (9)	−0.0061 (8)	−0.0046 (7)	−0.0111 (9)
N4	0.0385 (8)	0.0289 (8)	0.0338 (8)	−0.0064 (6)	−0.0031 (6)	−0.0028 (6)
N5	0.0363 (9)	0.0317 (9)	0.0407 (9)	−0.0006 (7)	−0.0023 (7)	−0.0001 (7)
O1	0.0513 (9)	0.0413 (9)	0.0904 (12)	−0.0006 (7)	−0.0138 (8)	−0.0095 (8)
O2	0.1085 (16)	0.0526 (11)	0.1104 (16)	0.0045 (11)	−0.0328 (12)	0.0230 (11)
O3	0.1177 (16)	0.0729 (12)	0.0587 (11)	−0.0338 (11)	−0.0321 (11)	0.0242 (9)
O4	0.0656 (10)	0.0825 (12)	0.0461 (9)	−0.0069 (9)	0.0138 (8)	−0.0138 (8)
O5	0.0638 (10)	0.0524 (10)	0.0677 (10)	0.0059 (8)	−0.0006 (8)	0.0038 (8)
O6	0.0623 (10)	0.0701 (11)	0.0503 (9)	−0.0117 (8)	0.0055 (7)	0.0075 (8)
O7	0.0693 (11)	0.0822 (12)	0.0591 (10)	−0.0126 (9)	0.0035 (8)	−0.0371 (9)
O8	0.0599 (9)	0.0308 (7)	0.0409 (7)	−0.0161 (6)	0.0051 (6)	−0.0049 (6)
O9	0.0948 (12)	0.0441 (9)	0.0388 (8)	−0.0271 (8)	0.0105 (8)	0.0014 (6)

Geometric parameters (Å, º) top

C1—O1	1.244 (2)	C14—H14B	0.970
C1—C2	1.450 (3)	C15—N4	1.479 (2)
C1—C6	1.453 (3)	C15—C16	1.509 (3)
C2—C3	1.369 (3)	C15—H15A	0.970
C2—N1	1.466 (3)	C15—H15B	0.970
C3—C4	1.375 (3)	C16—N5	1.493 (2)
C3—H3	0.930	C16—H16A	0.970
C4—C5	1.382 (2)	C16—H16B	0.970
C4—N2	1.447 (2)	C17—N5	1.490 (2)
C5—C6	1.362 (2)	C17—C18	1.505 (2)
C5—H5	0.930	C17—H17A	0.970
C6—N3	1.456 (2)	C17—H17B	0.970
C7—O9	1.209 (2)	C18—N4	1.476 (2)
C7—O8	1.313 (2)	C18—H18A	0.970
C7—C8	1.494 (2)	C18—H18B	0.970
C8—C9	1.385 (2)	C19—N5	1.489 (2)
C8—C13	1.391 (2)	C19—H19A	0.960
C9—C10	1.382 (3)	C19—H19B	0.960
C9—H9	0.930	C19—H19C	0.960
C10—C11	1.390 (3)	N1—O2	1.215 (3)
C10—H10	0.930	N1—O3	1.226 (3)
C11—C12	1.386 (2)	N2—O4	1.225 (2)
C11—C14	1.509 (2)	N2—O5	1.227 (2)
C12—C13	1.386 (2)	N3—O7	1.223 (2)
C12—H12	0.930	N3—O6	1.226 (2)
C13—H13	0.930	N5—H5A	0.89 (2)
C14—N4	1.491 (2)	O8—H8	0.820
C14—H14A	0.970

O1—C1—C2	125.88 (19)	C16—C15—H15A	109.3
O1—C1—C6	122.99 (19)	N4—C15—H15B	109.3
C2—C1—C6	111.10 (16)	C16—C15—H15B	109.3
C3—C2—C1	123.83 (18)	H15A—C15—H15B	108.0
C3—C2—N1	115.70 (19)	N5—C16—C15	111.14 (14)
C1—C2—N1	120.46 (19)	N5—C16—H16A	109.4
C2—C3—C4	120.19 (18)	C15—C16—H16A	109.4
C2—C3—H3	119.9	N5—C16—H16B	109.4
C4—C3—H3	119.9	C15—C16—H16B	109.4
C3—C4—C5	120.72 (17)	H16A—C16—H16B	108.0
C3—C4—N2	119.81 (17)	N5—C17—C18	110.62 (15)
C5—C4—N2	119.47 (17)	N5—C17—H17A	109.5
C6—C5—C4	118.97 (17)	C18—C17—H17A	109.5
C6—C5—H5	120.5	N5—C17—H17B	109.5
C4—C5—H5	120.5	C18—C17—H17B	109.5
C5—C6—C1	125.15 (17)	H17A—C17—H17B	108.1
C5—C6—N3	115.99 (17)	N4—C18—C17	110.48 (14)
C1—C6—N3	118.84 (16)	N4—C18—H18A	109.6
O9—C7—O8	123.05 (17)	C17—C18—H18A	109.6
O9—C7—C8	123.12 (16)	N4—C18—H18B	109.6
O8—C7—C8	113.82 (15)	C17—C18—H18B	109.6
C9—C8—C13	119.15 (16)	H18A—C18—H18B	108.1
C9—C8—C7	118.80 (16)	N5—C19—H19A	109.5
C13—C8—C7	122.01 (15)	N5—C19—H19B	109.5
C10—C9—C8	120.65 (17)	H19A—C19—H19B	109.5
C10—C9—H9	119.7	N5—C19—H19C	109.5
C8—C9—H9	119.7	H19A—C19—H19C	109.5
C9—C10—C11	120.59 (16)	H19B—C19—H19C	109.5
C9—C10—H10	119.7	O2—N1—O3	122.7 (2)
C11—C10—H10	119.7	O2—N1—C2	119.6 (2)
C12—C11—C10	118.64 (16)	O3—N1—C2	117.7 (2)
C12—C11—C14	120.67 (16)	O4—N2—O5	123.64 (17)
C10—C11—C14	120.69 (16)	O4—N2—C4	117.71 (17)
C13—C12—C11	121.00 (17)	O5—N2—C4	118.64 (16)
C13—C12—H12	119.5	O7—N3—O6	123.34 (18)
C11—C12—H12	119.5	O7—N3—C6	118.32 (18)
C12—C13—C8	119.95 (16)	O6—N3—C6	118.34 (17)
C12—C13—H13	120.0	C18—N4—C15	110.02 (14)
C8—C13—H13	120.0	C18—N4—C14	112.50 (13)
N4—C14—C11	115.44 (15)	C15—N4—C14	111.92 (14)
N4—C14—H14A	108.4	C17—N5—C19	111.33 (15)
C11—C14—H14A	108.4	C17—N5—C16	109.59 (15)
N4—C14—H14B	108.4	C19—N5—C16	112.03 (15)
C11—C14—H14B	108.4	C17—N5—H5A	106.5 (13)
H14A—C14—H14B	107.5	C19—N5—H5A	105.9 (13)
N4—C15—C16	111.45 (14)	C16—N5—H5A	111.3 (13)
N4—C15—H15A	109.3	C7—O8—H8	109.5

O1—C1—C2—C3	−176.28 (19)	C9—C8—C13—C12	0.4 (3)
C6—C1—C2—C3	2.0 (3)	C7—C8—C13—C12	−177.54 (16)
O1—C1—C2—N1	2.5 (3)	C12—C11—C14—N4	−90.9 (2)
C6—C1—C2—N1	−179.22 (16)	C10—C11—C14—N4	88.9 (2)
C1—C2—C3—C4	−1.1 (3)	N4—C15—C16—N5	−55.9 (2)
N1—C2—C3—C4	−179.94 (17)	N5—C17—C18—N4	59.5 (2)
C2—C3—C4—C5	0.3 (3)	C3—C2—N1—O2	−173.7 (2)
C2—C3—C4—N2	−179.94 (17)	C1—C2—N1—O2	7.4 (3)
C3—C4—C5—C6	−0.7 (3)	C3—C2—N1—O3	6.7 (3)
N2—C4—C5—C6	179.59 (16)	C1—C2—N1—O3	−172.20 (18)
C4—C5—C6—C1	1.9 (3)	C3—C4—N2—O4	2.3 (3)
C4—C5—C6—N3	−179.92 (16)	C5—C4—N2—O4	−177.91 (17)
O1—C1—C6—C5	175.93 (18)	C3—C4—N2—O5	−178.37 (18)
C2—C1—C6—C5	−2.4 (3)	C5—C4—N2—O5	1.4 (3)
O1—C1—C6—N3	−2.2 (3)	C5—C6—N3—O7	146.71 (18)
C2—C1—C6—N3	179.41 (16)	C1—C6—N3—O7	−35.0 (2)
O9—C7—C8—C9	13.3 (3)	C5—C6—N3—O6	−32.8 (2)
O8—C7—C8—C9	−165.86 (16)	C1—C6—N3—O6	145.57 (18)
O9—C7—C8—C13	−168.83 (19)	C17—C18—N4—C15	−58.31 (19)
O8—C7—C8—C13	12.1 (2)	C17—C18—N4—C14	176.17 (15)
C13—C8—C9—C10	−0.7 (3)	C16—C15—N4—C18	56.68 (19)
C7—C8—C9—C10	177.30 (16)	C16—C15—N4—C14	−177.48 (15)
C8—C9—C10—C11	−0.3 (3)	C11—C14—N4—C18	64.0 (2)
C9—C10—C11—C12	1.5 (3)	C11—C14—N4—C15	−60.5 (2)
C9—C10—C11—C14	−178.33 (16)	C18—C17—N5—C19	178.02 (17)
C10—C11—C12—C13	−1.8 (3)	C18—C17—N5—C16	−57.47 (19)
C14—C11—C12—C13	178.01 (16)	C15—C16—N5—C17	55.6 (2)
C11—C12—C13—C8	0.9 (3)	C15—C16—N5—C19	179.69 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···N4ⁱ	0.82	1.79	2.6006 (19)	172
N5—H5A···O1ⁱⁱ	0.89 (2)	1.89 (2)	2.734 (2)	156.9 (18)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₉N₂O₂⁺·C₆H₂N₃O₇⁻
M_r	463.41
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.3020 (12), 9.5993 (16), 15.131 (3)
α, β, γ (°)	86.448 (2), 79.145 (2), 79.950 (2)
V (Å³)	1025.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.965, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	5373, 3565, 2745
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 1.06
No. of reflections	3565
No. of parameters	305
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···N4ⁱ	0.82	1.79	2.6006 (19)	172.0
N5—H5A···O1ⁱⁱ	0.89 (2)	1.89 (2)	2.734 (2)	156.9 (18)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z+1.

Acknowledgements

QNMHA thanks R. L. Fine Chem, Bangalore, for a gift sample of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid. HSY thanks the University of Mysore for research facilities.

References

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