(E)-4-Amino-N′-(5-chloro-2-hy­droxy­benzyl­idene)benzohydrazide

Kargar, H.; Kia, R.; Tahir, M.N.

doi:10.1107/S1600536812025974

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2118-o2119

https://doi.org/10.1107/S1600536812025974

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(E)-4-Amino-N′-(5-chloro-2-hydroxybenzylidene)benzohydrazide

Hadi Kargar,^a ^* Reza Kia ^b ‡ and Muhammad Nawaz Tahir ^c ^*

^aDepartment of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, I. R. of IRAN, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^cDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: h.kargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 3 June 2012; accepted 7 June 2012; online 16 June 2012)

In the title hydrazide Schiff base compound, C₁₄H₁₂ClN₃O₂, the conformation around the C=N double bond is E. The dihedral angle between the benzene rings is 41.57 (14) Å. An intramolecular O—H⋯N hydrogen bond makes an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O (bifurcated acceptor) and N—H⋯N hydrogen bonds, forming chains along the a axis. The interesting feature of the crystal structure is the short intermolecular C⋯O [3.216 (3), 3.170 (3), and 2.992 (3) Å] contacts, one of which is significantly shorter than the sum of the van der Waals radii of these atoms [3.22 Å].

Related literature

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006 ); Karthikeyan et al. (2006 ). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012 ); Shi & Li (2012 ); Bakir & Green (2002 ). For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For van der Waals radii, see: Bondi (1964 ).

Experimental

Crystal data

C₁₄H₁₂ClN₃O₂
M_r = 289.72
Orthorhombic, P n a 2₁
a = 9.4243 (8) Å
b = 9.7975 (9) Å
c = 14.1924 (10) Å
V = 1310.45 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.916, T_max = 0.938
5390 measured reflections
2157 independent reflections
1871 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.084
S = 1.04
2157 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1661 Friedel pairs
Flack parameter: −0.02 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.584 (3)	145
N2—H2⋯O2ⁱ	0.98	1.98	2.951 (3)	169
N3—H3B⋯O2ⁱⁱ	0.96	2.09	3.004 (3)	159
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) $[-x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025974/su2449sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025974/su2449Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025974/su2449Isup3.cml

checkCIF report

Comment top

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and magnetism, and supramolecular architectures (Karthikeyan et al., 2006; Kucukguzel et al., 2006). Structures of Schiff bases derived from substituted 4-aminobenzohydrazide have been reported earlier (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002). In order to explore the structure of new Schiff base derivatives, the title compound was prepared and characterized crystallographically.

The title molecule, Fig. 1, has an E conformation around C═N double bond. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002). The dihedral angle between the substituted phenyl rings is 41.57 (14)Å. An intramolecular O—H···N hydrogen bond makes an S(6) ring motif (Bernstein et al., 1995).

In the crystal, molecules are linked through N—H···O (bifurcated acceptor) and N—H···N hydrogen bonds forming one-dimensional chains along the a axis. An interesting feature of the crystal structure is the short intermolecular C1···O1ⁱⁱⁱ [3.216 (3) Å; (iii) -1/2 + x, 3/2 - y, z], C6···O1ⁱⁱⁱ [3.170 (3) Å], and C7···O1ⁱⁱⁱ [2.992 (3) Å] contacts, in which one of them is significantly shorter than the sum of the van der Waals radii of these atoms [3.22Å; Bondi, 1964].

Related literature top

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006); Karthikeyan et al. (2006). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012); Shi & Li (2012); Bakir & Green (2002). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For van der Waals radii, see: Bondi (1964).

Experimental top

The title compound was synthesized by adding 1 mmol of methyl 4-aminobenzoate to a solution of 5-chlorosalicylaldehyde (1 mmol) in methanol (30 ml). The mixture was refluxed with stirring for 30 min and after cooling to room temperature a light-yellow precipitate was filtered and washed with diethylether and dried in air. Light-yellow prismatic crystals of the title compound, suitable for X-ray structure analysis, were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Structure description top

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006); Karthikeyan et al. (2006). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012); Shi & Li (2012); Bakir & Green (2002). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For van der Waals radii, see: Bondi (1964).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atom numbering. The dashed lines show the intramolecular O-H···N hydrogen bonds (see Table 1 for details).
	Fig. 2. A view along the a axis of crystal packing of the title compound, showing how the molecules are linked via N—H···O hydrogen bonds (dashed lines; see Table 1 for details). Only the H atoms involved in these interactions are shown.

(E)-4-Amino-N'-(5-chloro-2-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₂ClN₃O₂	F(000) = 600
M_r = 289.72	D_x = 1.468 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1125 reflections
a = 9.4243 (8) Å	θ = 2.5–27.4°
b = 9.7975 (9) Å	µ = 0.30 mm⁻¹
c = 14.1924 (10) Å	T = 296 K
V = 1310.45 (19) Å³	Prism, light-yellow
Z = 4	0.30 × 0.25 × 0.22 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2157 independent reflections
Radiation source: fine-focus sealed tube	1871 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 27.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→12
T_min = 0.916, T_max = 0.938	k = −12→9
5390 measured reflections	l = −14→17

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0457P)² + 0.1075P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2157 reflections	Δρ_max = 0.25 e Å⁻³
182 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1661 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (8)

Crystal data top

C₁₄H₁₂ClN₃O₂	V = 1310.45 (19) Å³
M_r = 289.72	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.4243 (8) Å	µ = 0.30 mm⁻¹
b = 9.7975 (9) Å	T = 296 K
c = 14.1924 (10) Å	0.30 × 0.25 × 0.22 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2157 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1871 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.938	R_int = 0.023
5390 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 0.25 e Å⁻³
S = 1.04	Δρ_min = −0.28 e Å⁻³
2157 reflections	Absolute structure: Flack (1983), 1661 Friedel pairs
182 parameters	Absolute structure parameter: −0.02 (8)
1 restraint

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
Cl1	0.25011 (8)	0.53141 (8)	−0.12609 (6)	0.0608 (2)
O1	−0.18920 (19)	0.6731 (2)	0.14787 (13)	0.0576 (6)
H1	−0.1557	0.6890	0.2001	0.086*
O2	−0.14326 (17)	0.8456 (2)	0.38803 (12)	0.0433 (5)
N1	0.0101 (2)	0.6912 (2)	0.27231 (13)	0.0357 (5)
N2	0.0530 (2)	0.7181 (2)	0.36316 (14)	0.0348 (5)
H2	0.1501	0.6912	0.3791	0.042*
N3	0.1425 (3)	0.8793 (3)	0.79456 (16)	0.0608 (7)
H3A	0.1989	0.8266	0.8306	0.073*
H3B	0.1185	0.9611	0.8284	0.073*
C1	0.0540 (3)	0.6151 (3)	0.11808 (16)	0.0343 (6)
C2	−0.0834 (3)	0.6413 (3)	0.08747 (18)	0.0401 (6)
C3	−0.1161 (3)	0.6341 (3)	−0.00784 (18)	0.0452 (7)
H3	−0.2084	0.6516	−0.0277	0.054*
C4	−0.0146 (3)	0.6016 (3)	−0.07299 (17)	0.0436 (7)
H4	−0.0368	0.5995	−0.1368	0.052*
C5	0.1210 (3)	0.5721 (3)	−0.04292 (18)	0.0409 (6)
C6	0.1556 (3)	0.5765 (3)	0.05102 (18)	0.0413 (6)
H6	0.2469	0.5538	0.0703	0.050*
C7	0.0965 (3)	0.6349 (3)	0.21540 (17)	0.0371 (6)
H7	0.1856	0.6069	0.2359	0.045*
C8	−0.0326 (3)	0.7949 (3)	0.41874 (17)	0.0337 (6)
C9	0.0153 (2)	0.8152 (3)	0.51641 (17)	0.0327 (6)
C10	0.1079 (3)	0.7271 (3)	0.56124 (18)	0.0451 (7)
H10	0.1439	0.6526	0.5284	0.054*
C11	0.1479 (3)	0.7471 (3)	0.65323 (18)	0.0492 (7)
H11	0.2087	0.6851	0.6820	0.059*
C12	0.0986 (3)	0.8585 (3)	0.70364 (17)	0.0397 (6)
C13	0.0065 (3)	0.9481 (3)	0.65961 (18)	0.0422 (6)
H13	−0.0274	1.0237	0.6922	0.051*
C14	−0.0354 (3)	0.9260 (3)	0.56763 (19)	0.0408 (6)
H14	−0.0987	0.9863	0.5394	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0686 (4)	0.0770 (5)	0.0367 (3)	0.0182 (4)	0.0054 (4)	−0.0052 (4)
O1	0.0410 (10)	0.0937 (18)	0.0380 (11)	0.0132 (11)	−0.0035 (9)	−0.0045 (12)
O2	0.0346 (9)	0.0579 (12)	0.0375 (11)	0.0050 (8)	−0.0085 (8)	0.0032 (10)
N1	0.0394 (11)	0.0443 (13)	0.0233 (10)	−0.0043 (9)	−0.0059 (9)	0.0007 (9)
N2	0.0343 (10)	0.0477 (13)	0.0223 (10)	0.0009 (10)	−0.0055 (9)	0.0001 (10)
N3	0.0859 (18)	0.0627 (19)	0.0338 (13)	0.0048 (14)	−0.0158 (12)	−0.0128 (13)
C1	0.0382 (14)	0.0355 (14)	0.0291 (13)	−0.0005 (11)	−0.0069 (11)	0.0009 (12)
C2	0.0394 (14)	0.0466 (18)	0.0342 (13)	−0.0009 (13)	−0.0055 (12)	0.0016 (13)
C3	0.0443 (16)	0.0535 (18)	0.0377 (15)	0.0016 (13)	−0.0122 (13)	−0.0011 (13)
C4	0.0592 (18)	0.0452 (16)	0.0265 (13)	0.0014 (13)	−0.0117 (12)	−0.0025 (13)
C5	0.0526 (16)	0.0383 (16)	0.0317 (13)	0.0027 (12)	−0.0010 (12)	−0.0010 (13)
C6	0.0414 (15)	0.0480 (16)	0.0345 (14)	0.0057 (13)	−0.0091 (11)	−0.0008 (13)
C7	0.0324 (13)	0.0469 (17)	0.0320 (13)	0.0001 (12)	−0.0075 (11)	0.0028 (13)
C8	0.0327 (13)	0.0370 (14)	0.0313 (13)	−0.0053 (11)	−0.0050 (11)	0.0045 (12)
C9	0.0303 (13)	0.0398 (14)	0.0279 (12)	−0.0013 (11)	−0.0008 (10)	0.0000 (11)
C10	0.0593 (17)	0.0438 (17)	0.0323 (15)	0.0127 (14)	−0.0052 (13)	−0.0053 (13)
C11	0.0669 (18)	0.0450 (16)	0.0357 (14)	0.0155 (14)	−0.0133 (14)	0.0005 (13)
C12	0.0451 (15)	0.0457 (17)	0.0283 (12)	−0.0045 (13)	0.0010 (12)	−0.0025 (13)
C13	0.0424 (14)	0.0446 (15)	0.0395 (15)	0.0015 (13)	0.0030 (12)	−0.0095 (14)
C14	0.0367 (13)	0.0452 (16)	0.0406 (15)	0.0060 (13)	−0.0019 (12)	0.0021 (13)

Geometric parameters (Å, º) top

Cl1—C5	1.742 (3)	C4—C5	1.378 (4)
O1—C2	1.351 (3)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.373 (3)
O2—C8	1.235 (3)	C6—H6	0.9300
N1—C7	1.272 (3)	C7—H7	0.9300
N1—N2	1.377 (3)	C8—C9	1.471 (3)
N2—C8	1.357 (3)	C9—C10	1.382 (4)
N2—H2	0.9783	C9—C14	1.392 (4)
N3—C12	1.370 (3)	C10—C11	1.373 (4)
N3—H3A	0.9001	C10—H10	0.9300
N3—H3B	0.9616	C11—C12	1.385 (4)
C1—C2	1.390 (3)	C11—H11	0.9300
C1—C6	1.402 (3)	C12—C13	1.383 (4)
C1—C7	1.451 (3)	C13—C14	1.381 (4)
C2—C3	1.389 (4)	C13—H13	0.9300
C3—C4	1.368 (4)	C14—H14	0.9300
C3—H3	0.9300

C2—O1—H1	109.5	C1—C6—H6	119.8
C7—N1—N2	119.3 (2)	N1—C7—C1	119.1 (2)
C8—N2—N1	118.43 (19)	N1—C7—H7	120.5
C8—N2—H2	124.8	C1—C7—H7	120.5
N1—N2—H2	116.1	O2—C8—N2	121.4 (2)
C12—N3—H3A	128.9	O2—C8—C9	122.5 (2)
C12—N3—H3B	121.5	N2—C8—C9	116.1 (2)
H3A—N3—H3B	109.5	C10—C9—C14	117.6 (2)
C2—C1—C6	118.3 (2)	C10—C9—C8	122.9 (2)
C2—C1—C7	122.0 (2)	C14—C9—C8	119.5 (2)
C6—C1—C7	119.6 (2)	C11—C10—C9	121.5 (3)
O1—C2—C3	117.8 (2)	C11—C10—H10	119.3
O1—C2—C1	122.1 (2)	C9—C10—H10	119.3
C3—C2—C1	120.1 (2)	C10—C11—C12	120.8 (3)
C4—C3—C2	121.0 (2)	C10—C11—H11	119.6
C4—C3—H3	119.5	C12—C11—H11	119.6
C2—C3—H3	119.5	N3—C12—C13	121.4 (3)
C3—C4—C5	119.2 (2)	N3—C12—C11	120.2 (3)
C3—C4—H4	120.4	C13—C12—C11	118.5 (2)
C5—C4—H4	120.4	C14—C13—C12	120.5 (3)
C6—C5—C4	121.0 (2)	C14—C13—H13	119.8
C6—C5—Cl1	119.9 (2)	C12—C13—H13	119.8
C4—C5—Cl1	119.1 (2)	C13—C14—C9	121.2 (2)
C5—C6—C1	120.4 (2)	C13—C14—H14	119.4
C5—C6—H6	119.8	C9—C14—H14	119.4

C7—N1—N2—C8	170.8 (2)	N1—N2—C8—O2	−3.4 (3)
C6—C1—C2—O1	177.0 (3)	N1—N2—C8—C9	177.3 (2)
C7—C1—C2—O1	−7.1 (4)	O2—C8—C9—C10	157.6 (3)
C6—C1—C2—C3	−2.4 (4)	N2—C8—C9—C10	−23.1 (3)
C7—C1—C2—C3	173.6 (3)	O2—C8—C9—C14	−21.3 (4)
O1—C2—C3—C4	−179.6 (3)	N2—C8—C9—C14	158.0 (2)
C1—C2—C3—C4	−0.2 (5)	C14—C9—C10—C11	0.5 (4)
C2—C3—C4—C5	1.8 (4)	C8—C9—C10—C11	−178.4 (3)
C3—C4—C5—C6	−0.8 (4)	C9—C10—C11—C12	−1.4 (5)
C3—C4—C5—Cl1	−179.8 (2)	C10—C11—C12—N3	−178.2 (3)
C4—C5—C6—C1	−1.8 (4)	C10—C11—C12—C13	1.0 (4)
Cl1—C5—C6—C1	177.2 (2)	N3—C12—C13—C14	179.4 (3)
C2—C1—C6—C5	3.4 (4)	C11—C12—C13—C14	0.3 (4)
C7—C1—C6—C5	−172.7 (3)	C12—C13—C14—C9	−1.1 (4)
N2—N1—C7—C1	−175.9 (2)	C10—C9—C14—C13	0.7 (4)
C2—C1—C7—N1	−7.4 (4)	C8—C9—C14—C13	179.7 (2)
C6—C1—C7—N1	168.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.584 (3)	145
N2—H2···O2ⁱ	0.98	1.98	2.951 (3)	169
N3—H3B···O2ⁱⁱ	0.96	2.09	3.004 (3)	159

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClN₃O₂
M_r	289.72
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	9.4243 (8), 9.7975 (9), 14.1924 (10)
V (Å³)	1310.45 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.30 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.916, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	5390, 2157, 1871
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.084, 1.04
No. of reflections	2157
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28
Absolute structure	Flack (1983), 1661 Friedel pairs
Absolute structure parameter	−0.02 (8)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008)', SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.584 (3)	145
N2—H2···O2ⁱ	0.98	1.98	2.951 (3)	169
N3—H3B···O2ⁱⁱ	0.96	2.09	3.004 (3)	159

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

Footnotes

‡Present address: Structural Dynamics of (Bio)Chemical Systems, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany.

Acknowledgements

HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for the research facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bakir, M. & Green, O. (2002). Acta Cryst. C58, o263–o265. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bondi, A. (1964). J. Phys. Chem. 68, 441-452. Web of Science CrossRef CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482–7489. Web of Science CrossRef PubMed CAS Google Scholar
Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahi, F. & Gulluce, M. (2006). Eur. J. Med. Chem. 41, 353–359. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Z.-F. & Li, J.-M. (2012). Acta Cryst. E68, o1546–o1547. CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, S.-Q. (2012). Acta Cryst. E68, o1320. CSD CrossRef IUCr Journals Google Scholar