1-Methyl­piperazine-1,4-dium bis­(hydrogen oxalate)

Essid, M.; Marouani, H.; Rzaigui, M.

doi:10.1107/S1600536814003559

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o326-o327

doi:10.1107/S1600536814003559

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1-Methylpiperazine-1,4-dium bis(hydrogen oxalate)

Manel Essid,^a ^* Houda Marouani ^a and Mohamed Rzaigui ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
^*Correspondence e-mail: essidmanel@voila.fr

(Received 12 February 2014; accepted 17 February 2014; online 22 February 2014)

In the crystal structure of the title compound, C₅H₁₄N₂²⁺·2HC₂O₄⁻, the two crystallographically independent hydrogen oxalate anions are linked by strong intermolecular O—H⋯O hydrogen bonds, forming two independent corrugated chains parallel to the b axis. These chains are further connected by N—H⋯O and C—H⋯O hydrogen bonds originating from the organic cations, forming a three-dimensional network. The diprotonated piperazine ring adopts a chair conformation, with the methyl group occupying an equatorial position.

CCDC reference: 987380

Related literature

For the biological activity of piperazines, see: Conrado et al. (2008 ); Brockunier et al. (2004 ); Bogatcheva et al. (2006 ). For related structures, see: Essid et al. (2013 ); Dutkiewicz et al. (2011 ); Vaidhyanathan et al. (2002 ); Ejsmont & Zaleski (2006 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₅H₁₄N₂²⁺·2C₂HO₄⁻
M_r = 280.24
Monoclinic, C 2/c
a = 15.649 (2) Å
b = 5.681 (3) Å
c = 27.230 (2) Å
β = 104.05 (2)°
V = 2348.4 (13) Å³
Z = 8
Ag Kα radiation
λ = 0.56083 Å
μ = 0.08 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
7879 measured reflections
5758 independent reflections
3621 reflections with I > 2σ(I)
R_int = 0.027
2 standard reflections every 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.162
S = 1.01
5757 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.82	1.72	2.5242 (17)	167
O5—H5⋯O8ⁱⁱ	0.82	1.74	2.5467 (16)	169
N1—H1⋯O4	0.91	1.92	2.7452 (15)	151
N1—H1⋯O2	0.91	2.27	2.9085 (13)	127
N2—H2C⋯O8ⁱⁱⁱ	0.90	2.03	2.8080 (14)	144
N2—H2C⋯O6ⁱⁱⁱ	0.90	2.51	3.2564 (19)	141
N2—H2D⋯O7^iv	0.90	1.93	2.7633 (16)	154
N2—H2D⋯O5^iv	0.90	2.32	2.9243 (13)	125
C1—H1B⋯O3^v	0.96	2.45	3.2653 (19)	142
C2—H2A⋯O4ⁱ	0.97	2.44	3.3533 (18)	157
C3—H3A⋯O6^vi	0.97	2.49	3.4334 (18)	163
C3—H3B⋯O8ⁱⁱ	0.97	2.29	3.2319 (15)	164
C4—H4B⋯O7^vii	0.97	2.43	3.3665 (18)	163
C5—H5A⋯O3^viii	0.97	2.28	3.2269 (16)	165
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) $[-x+1, y-1, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (v) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ ; (vi) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (vii) $[x+{\script{1\over 2}}, y-{\script{3\over 2}}, z]$ ; (viii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 987380

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814003559/zl2578sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003559/zl2578Isup2.hkl

checkCIF report

Comment top

Piperazine and its derivatives have been intensively investigated owing to their interesting pharmacological, cardiovascular and autonomic properties (Conrado et al., 2008). Piperazine derivatives are found in biologically active compounds across a number of different therapeutic areas such as antifungal, antibacterial, antimalarial, antipsychotic, antidepressant and antitumour activity against colon, prostate, breast, lung and leukemia tumors (Brockunier et al., 2004; Bogatcheva et al., 2006; Essid et al., 2013). In the present work, we report the preparation and the crystal structure of an organic proton transfer salt (C₅H₁₄N₂)²⁺·2(HC₂O₄)^-, (I). The asymmetric unit of (I) contains one 1-methylpiperazin-1,4-diium dication and two semi-oxalate anions (Fig. 1). 1-Methylpiperazine is diprotonated at atom N1 and N2 and oxalic acid is mono-deprotonated. The oxalate monoanions are essentially planar, with dihedral angles between the carboxylate groups of less than 4°. Two strong O–H···O (Table 1) hydrogen bonds generate linear oxalate chains running parallel to the b axis (Fig. 2). The geometrical parameters of these chains correlate well with the corresponding values found in related crystal structures (Essid et al., 2013; Vaidhyanathan et al., 2002; Ejsmont & Zaleski, 2006). Bond distances around atom C7 and C8 indicate a carboxylate group with delocalization of the negative charge between atoms O3 and O4, and between O7 and O8. In the hydrogenoxalate anion HC₂O₄^-, the H atoms are located at O2 and O5. The position of protonation is also indicated by elongation of the corresponding C–O distances [O2–C6 = 1.306 (2) Å, O5–C9 = 1.306 (1) Å]. The bond lengths of C6–C7 and C8–C9 are relatively long [1.553 (2) Å, 1.544 (2) Å] as expected for an oxalate anion. Geometrical parameters of the methylpiperazin-1,4-dium dications are found to be in agreement with those of another similar structure of methylpiperazin-1,4-diium dipicrate (Dutkiewicz et al., 2011). The cyclic amine adopts a chair conformation with the methyl group occupying an equatorial position, with puckering parameters: Q = 0.5772 (11) A, θ = 2.85 (11)° and φ = -174 (2)° (Cremer & Pople, 1975) and atoms N1 and N2 deviating by -0.308 (2) and 0.333 (2) Å from the least-squares plane defined by the remaining atoms in the ring. In addition, the crystal structure of [C₅H₁₄N₂](HC₂O₄)₂ is stabilized by ionic interactions between the 1-methylpiperazin-1,4-dium dications and the oxalate monoanions chains, as well as by a network of N–H···O and C–H···O hydrogen bonds (Fig. 3 and Table 1) such that all the hydrogen atoms bonded to nitrogen atoms participate in the formation of these hydrogen bonds, with donor-acceptor distances between 2.745 (2) and 3.433 (2) Å (Table 1).

Related literature top

For the biological activity of piperazines, see: Conrado et al. (2008); Brockunier et al. (2004); Bogatcheva et al. (2006). For related structures, see: Essid et al. (2013); Dutkiewicz et al. (2011); Vaidhyanathan et al. (2002); Ejsmont & Zaleski, (2006). For puckering parameters, see Cremer & Pople (1975).

Experimental top

An aqueous solution containing 2 mmol of H₂C₂O₄ in 20 ml of water was added to 1 mmol of 1-methylpiperazine in 10 ml of ethanol. The obtained solution was stirred at 333 K. When the solution became homogeneous it was cooled slowly and kept at room temperature. After several days, transparent colourless crystals formed. Crystals of the title compound, which remained stable under normal conditions of temperature and humidity, were isolated and subjected to X-ray diffraction analysis. M.p. 260°C. Main IR bands (KBr disc, cm^-1): (vs = very strong; s = strong; w = weak) 3025 w, 1619 s, 1470 s, 1410 s, 1356 vs, 1269 vs, 1203 w, 1050 vs, 1022 s, 985 s, 713 s.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. An ORTEP view of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 45% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Projection of the corrugated hydrogen oxalate chains along the a axis.
	Fig. 3. Projection of (I) along the b axis. The H-atoms not involved in H-bonding are omitted.

1-Methylpiperazine-1,4-dium bis(hydrogen oxalate) top

Crystal data top

C₅H₁₄N₂²⁺·2C₂HO₄⁻	F(000) = 1184
M_r = 280.24	D_x = 1.585 Mg m⁻³
Monoclinic, C2/c	Ag Kα radiation, λ = 0.56083 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 15.649 (2) Å	θ = 9–11°
b = 5.681 (3) Å	µ = 0.08 mm⁻¹
c = 27.230 (2) Å	T = 293 K
β = 104.05 (2)°	Prism, colourless
V = 2348.4 (13) Å³	0.35 × 0.25 × 0.15 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.027
Radiation source: fine-focus sealed tube	θ_max = 28.0°, θ_min = 2.1°
Graphite monochromator	h = −26→25
non–profiled ω scans	k = −2→9
7879 measured reflections	l = −1→45
5758 independent reflections	2 standard reflections every 120 min
3621 reflections with I > 2σ(I)	intensity decay: none

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0887P)² + 0.6525P] where P = (F_o² + 2F_c²)/3
5757 reflections	(Δ/σ)_max = 0.006
175 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₅H₁₄N₂²⁺·2C₂HO₄⁻	V = 2348.4 (13) Å³
M_r = 280.24	Z = 8
Monoclinic, C2/c	Ag Kα radiation, λ = 0.56083 Å
a = 15.649 (2) Å	µ = 0.08 mm⁻¹
b = 5.681 (3) Å	T = 293 K
c = 27.230 (2) Å	0.35 × 0.25 × 0.15 mm
β = 104.05 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.027
7879 measured reflections	2 standard reflections every 120 min
5758 independent reflections	intensity decay: none
3621 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
5757 reflections	Δρ_min = −0.40 e Å⁻³
175 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
O5	0.26348 (5)	0.43588 (15)	0.19137 (4)	0.02858 (19)
H5	0.2892	0.3099	0.1980	0.043*
O6	0.39346 (6)	0.58784 (19)	0.23195 (5)	0.0436 (3)
O7	0.19490 (5)	0.86264 (16)	0.17619 (4)	0.02856 (19)
O8	0.32494 (5)	1.02361 (15)	0.21317 (4)	0.02746 (18)
C8	0.27389 (6)	0.85255 (19)	0.19799 (4)	0.02018 (18)
C9	0.31747 (7)	0.60820 (19)	0.20900 (4)	0.02266 (19)
O1	0.12751 (6)	−0.01254 (18)	0.05548 (4)	0.0373 (2)
O2	0.26291 (6)	0.13819 (16)	0.08184 (4)	0.0348 (2)
H2	0.2366	0.2642	0.0780	0.052*
O3	0.20184 (6)	−0.45041 (16)	0.06515 (4)	0.0331 (2)
O4	0.33311 (5)	−0.28288 (16)	0.09557 (4)	0.0334 (2)
C6	0.20627 (7)	−0.03411 (19)	0.07029 (5)	0.0231 (2)
C7	0.25214 (7)	−0.27840 (19)	0.07768 (4)	0.02206 (19)
N1	0.45019 (6)	0.07065 (18)	0.09040 (4)	0.02256 (18)
H1	0.4022	−0.0041	0.0963	0.027*
N2	0.57669 (6)	0.01455 (19)	0.18579 (4)	0.0264 (2)
H2C	0.5933	−0.0381	0.2179	0.032*
H2D	0.6228	0.0897	0.1786	0.032*
C1	0.42704 (10)	0.1657 (3)	0.03769 (5)	0.0418 (3)
H1A	0.3819	0.2830	0.0347	0.063*
H1B	0.4060	0.0401	0.0143	0.063*
H1C	0.4783	0.2351	0.0302	0.063*
C2	0.47453 (7)	0.2672 (2)	0.12710 (5)	0.0261 (2)
H2A	0.4245	0.3722	0.1237	0.031*
H2B	0.5225	0.3562	0.1193	0.031*
C3	0.50225 (7)	0.1799 (2)	0.18088 (5)	0.0270 (2)
H3A	0.5198	0.3118	0.2037	0.032*
H3B	0.4532	0.1011	0.1899	0.032*
C4	0.55098 (8)	−0.1872 (2)	0.15092 (5)	0.0298 (2)
H4A	0.5024	−0.2710	0.1593	0.036*
H4B	0.6002	−0.2952	0.1547	0.036*
C5	0.52395 (7)	−0.1014 (2)	0.09704 (5)	0.0284 (2)
H5A	0.5739	−0.0274	0.0881	0.034*
H5B	0.5057	−0.2342	0.0746	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0224 (3)	0.0150 (3)	0.0441 (5)	0.0008 (3)	−0.0001 (3)	−0.0021 (3)
O6	0.0219 (4)	0.0272 (5)	0.0706 (7)	0.0024 (3)	−0.0106 (4)	0.0053 (5)
O7	0.0187 (3)	0.0206 (4)	0.0417 (5)	0.0014 (3)	−0.0019 (3)	0.0026 (3)
O8	0.0244 (4)	0.0164 (3)	0.0378 (5)	−0.0035 (3)	0.0001 (3)	−0.0013 (3)
C8	0.0195 (4)	0.0160 (4)	0.0237 (4)	0.0000 (3)	0.0026 (3)	0.0004 (3)
C9	0.0187 (4)	0.0172 (4)	0.0299 (5)	0.0003 (3)	0.0016 (3)	0.0008 (4)
O1	0.0189 (4)	0.0270 (5)	0.0608 (6)	0.0032 (3)	−0.0003 (4)	0.0064 (4)
O2	0.0218 (4)	0.0144 (3)	0.0647 (6)	−0.0003 (3)	0.0039 (4)	−0.0006 (4)
O3	0.0243 (4)	0.0166 (4)	0.0532 (6)	−0.0030 (3)	−0.0006 (4)	−0.0024 (4)
O4	0.0180 (3)	0.0194 (4)	0.0588 (6)	0.0012 (3)	0.0011 (3)	0.0037 (4)
C6	0.0204 (4)	0.0166 (4)	0.0308 (5)	0.0008 (3)	0.0032 (4)	0.0021 (4)
C7	0.0196 (4)	0.0146 (4)	0.0304 (5)	−0.0001 (3)	0.0029 (3)	0.0002 (4)
N1	0.0172 (3)	0.0229 (4)	0.0255 (4)	−0.0018 (3)	0.0012 (3)	0.0008 (3)
N2	0.0183 (4)	0.0270 (5)	0.0298 (5)	−0.0009 (3)	−0.0022 (3)	0.0022 (4)
C1	0.0363 (6)	0.0563 (10)	0.0291 (6)	−0.0029 (7)	0.0009 (5)	0.0108 (6)
C2	0.0234 (4)	0.0174 (4)	0.0347 (6)	0.0014 (4)	0.0018 (4)	−0.0006 (4)
C3	0.0220 (4)	0.0276 (5)	0.0298 (5)	0.0005 (4)	0.0034 (4)	−0.0054 (4)
C4	0.0229 (5)	0.0185 (5)	0.0437 (7)	0.0031 (4)	−0.0006 (4)	0.0006 (5)
C5	0.0221 (4)	0.0259 (5)	0.0367 (6)	0.0013 (4)	0.0061 (4)	−0.0075 (5)

Geometric parameters (Å, º) top

O5—C9	1.3061 (14)	N2—C4	1.4805 (17)
O5—H5	0.8200	N2—H2C	0.9000
O6—C9	1.2070 (13)	N2—H2D	0.9000
O7—C8	1.2358 (12)	C1—H1A	0.9600
O8—C8	1.2622 (13)	C1—H1B	0.9600
C8—C9	1.5437 (16)	C1—H1C	0.9600
O1—C6	1.2063 (13)	C2—C3	1.5068 (18)
O2—C6	1.3067 (14)	C2—H2A	0.9700
O2—H2	0.8200	C2—H2B	0.9700
O3—C7	1.2493 (14)	C3—H3A	0.9700
O4—C7	1.2424 (13)	C3—H3B	0.9700
C6—C7	1.5530 (16)	C4—C5	1.5059 (19)
N1—C2	1.4854 (16)	C4—H4A	0.9700
N1—C5	1.4897 (15)	C4—H4B	0.9700
N1—C1	1.4934 (17)	C5—H5A	0.9700
N1—H1	0.9100	C5—H5B	0.9700
N2—C3	1.4770 (15)

C9—O5—H5	109.5	H1A—C1—H1B	109.5
O7—C8—O8	126.96 (10)	N1—C1—H1C	109.5
O7—C8—C9	118.57 (9)	H1A—C1—H1C	109.5
O8—C8—C9	114.46 (9)	H1B—C1—H1C	109.5
O6—C9—O5	125.91 (11)	N1—C2—C3	111.87 (10)
O6—C9—C8	121.33 (10)	N1—C2—H2A	109.2
O5—C9—C8	112.75 (9)	C3—C2—H2A	109.2
C6—O2—H2	109.5	N1—C2—H2B	109.2
O1—C6—O2	125.63 (11)	C3—C2—H2B	109.2
O1—C6—C7	122.46 (10)	H2A—C2—H2B	107.9
O2—C6—C7	111.90 (9)	N2—C3—C2	109.40 (10)
O4—C7—O3	127.31 (10)	N2—C3—H3A	109.8
O4—C7—C6	117.67 (9)	C2—C3—H3A	109.8
O3—C7—C6	115.01 (9)	N2—C3—H3B	109.8
C2—N1—C5	110.32 (9)	C2—C3—H3B	109.8
C2—N1—C1	109.73 (11)	H3A—C3—H3B	108.2
C5—N1—C1	110.72 (11)	N2—C4—C5	110.04 (10)
C2—N1—H1	108.7	N2—C4—H4A	109.7
C5—N1—H1	108.7	C5—C4—H4A	109.7
C1—N1—H1	108.7	N2—C4—H4B	109.7
C3—N2—C4	110.41 (9)	C5—C4—H4B	109.7
C3—N2—H2C	109.6	H4A—C4—H4B	108.2
C4—N2—H2C	109.6	N1—C5—C4	110.90 (10)
C3—N2—H2D	109.6	N1—C5—H5A	109.5
C4—N2—H2D	109.6	C4—C5—H5A	109.5
H2C—N2—H2D	108.1	N1—C5—H5B	109.5
N1—C1—H1A	109.5	C4—C5—H5B	109.5
N1—C1—H1B	109.5	H5A—C5—H5B	108.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.72	2.5242 (17)	167
O5—H5···O8ⁱⁱ	0.82	1.74	2.5467 (16)	169
N1—H1···O4	0.91	1.92	2.7452 (15)	151
N1—H1···O2	0.91	2.27	2.9085 (13)	127
N2—H2C···O8ⁱⁱⁱ	0.90	2.03	2.8080 (14)	144
N2—H2C···O6ⁱⁱⁱ	0.90	2.51	3.2564 (19)	141
N2—H2D···O7^iv	0.90	1.93	2.7633 (16)	154
N2—H2D···O5^iv	0.90	2.32	2.9243 (13)	125
C1—H1B···O3^v	0.96	2.45	3.2653 (19)	142
C2—H2A···O4ⁱ	0.97	2.44	3.3533 (18)	157
C3—H3A···O6^vi	0.97	2.49	3.4334 (18)	163
C3—H3B···O8ⁱⁱ	0.97	2.29	3.2319 (15)	164
C4—H4B···O7^vii	0.97	2.43	3.3665 (18)	163
C5—H5A···O3^viii	0.97	2.28	3.2269 (16)	165

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.72	2.5242 (17)	166.9
O5—H5···O8ⁱⁱ	0.82	1.74	2.5467 (16)	169.3
N1—H1···O4	0.91	1.92	2.7452 (15)	150.7
N1—H1···O2	0.91	2.27	2.9085 (13)	127.0
N2—H2C···O8ⁱⁱⁱ	0.90	2.03	2.8080 (14)	144.0
N2—H2C···O6ⁱⁱⁱ	0.90	2.51	3.2564 (19)	140.9
N2—H2D···O7^iv	0.90	1.93	2.7633 (16)	153.6
N2—H2D···O5^iv	0.90	2.32	2.9243 (13)	124.9
C1—H1B···O3^v	0.96	2.45	3.2653 (19)	142.3
C2—H2A···O4ⁱ	0.97	2.44	3.3533 (18)	157.2
C3—H3A···O6^vi	0.97	2.49	3.4334 (18)	163.3
C3—H3B···O8ⁱⁱ	0.97	2.29	3.2319 (15)	163.6
C4—H4B···O7^vii	0.97	2.43	3.3665 (18)	162.6
C5—H5A···O3^viii	0.97	2.28	3.2269 (16)	165.4

Acknowledgements

This work was supported by the Tunisian Ministry of High Education Scientific Research.

References

Bogatcheva, E., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Barbosa, F., Einck, L., Nacy, C. A. & Protopopova, M. (2006). J. Med. Chem. 49, 3045–3048. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Brockunier, L. L., He, J., Colwell, L. F. Jr, Habulihaz, B., He, H., Leiting, B., Lyons, K. A., Marsilio, F., Patel, R. A., Teffera, Y., Wu, J. K., Thornberry, N. A., Weber, A. E. & Parmee, E. R. (2004). Bioorg. Med. Chem. Lett. 14, 4763–4766. Web of Science CrossRef PubMed CAS Google Scholar
Conrado, D. J., Verli, H., Neves, G., Fraga, C. A., Barreiro, E. J., Rates, S. M. & Dalla-Costa, T. (2008). J. Pharm. Pharmacol. 60, 699–707. Web of Science CrossRef PubMed CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dutkiewicz, G., Samshuddin, S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2011). Acta Cryst. E67, o390–o391. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ejsmont, K. & Zaleski, J. (2006). Acta Cryst. E62, o3879–o3880. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Essid, M., Marouani, H., Al-Deyab, S. S. & Rzaigui, M. (2013). Acta Cryst. E69, o1279. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vaidhyanathan, R., Natarajan, S. & Rao, C. N. R. (2002). J. Mol. Struct. 608, 123–133. Web of Science CSD CrossRef CAS Google Scholar