4-[(2,5-Dimethyl­anilino)acet­yl]-3,4-di­hydro­quinoxalin-2(1H)-one

Nasir, W.; Munawar, M.A.; Ahmad, S.; Nadeem, S.; Shahid, M.

doi:10.1107/S1600536809045991

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3006

doi:10.1107/S1600536809045991

Open

access

4-[(2,5-Dimethylanilino)acetyl]-3,4-dihydroquinoxalin-2(1H)-one

Waqar Nasir,^a Munawar Ali Munawar,^a ^* Saeed Ahmad,^b Sohail Nadeem ^a and Muhammad Shahid ^a

^aInstitute of Chemistry, University of the Punjab, New Campus, Lahore, Pakistan, and ^bInstitute of Chemistry, Gomal University, D. I. Khan, Pakistan
^*Correspondence e-mail: munawaralimunawar@yahoo.com

(Received 1 November 2009; accepted 2 November 2009; online 7 November 2009)

In the title compound, C₁₈H₁₉N₃O₂, the dihedral angle between the benzene rings is 20.47 (10)° and an intramolecular N—H⋯O hydrogen bond occurs, generating an S(5) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds lead to R₂²(8) loops.

Related literature

For background to the biological activity of quinoxalines, see: Khan (2008 ); Miyashiro et al. (2009 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₉N₃O₂
M_r = 309.36
Triclinic, $[P \overline 1]$
a = 5.3806 (2) Å
b = 12.3580 (6) Å
c = 13.2812 (6) Å
α = 62.878 (2)°
β = 84.135 (2)°
γ = 80.835 (3)°
V = 775.53 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.38 × 0.17 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.967, T_max = 0.995
16710 measured reflections
3803 independent reflections
2277 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.02
3803 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 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
N3—H2N⋯O2	0.85 (2)	2.20 (2)	2.620 (2)	110.0 (16)
N1—H1N⋯O1ⁱ	0.91 (2)	1.93 (2)	2.8405 (19)	176.9 (18)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045991/hb5210sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045991/hb5210Isup2.hkl

checkCIF report

Comment top

Quinoxalines represent an important class of nitrogen hetrocycles possessing wide range of biological activities (e.g. Khan, 2008). Moreover, several quinoxalines have been reported as inhibitors of, e.g. poly(ADP-ribose)polymerase-1 (Miyashiro et al., 2009). During our research we tried to synthesize novel quinoxaline derivatives which may possess enhanced biological activities.

The pyrazinone ring in the quinoxaline system have gained envelop shape to some extent with the r.m.s. deviation (0.1637 A°). The intramolecular hydrogen bonding present in the molecule give rise to the formation of five membered ring motif S(5) (Bernstein, et al., 1995) which is oriented at a dihedral angle of 28.13 (0.24) ° with respect to pyrazinone ring. The dihedral angle between planar p-xylene and pyrazinone ring is 21.31 (0.09) °. Further more symmetry related N–H···O type hydrogen bonding helps to stabilize the crystal structure of the molecule by forming eight membered ring motif R₂²8.

Related literature top

For background to the biological activity of quinoxalines, see: Khan (2008); Miyashiro et al. (2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

2,5 Dimethyl aniline (0.67 g, 5.57 mmol) added to the suspension of 4-(Chloroacetyl)-3,4-dihydroquinoxalin-2 (1H)-one (1.25 g, 5.57 mmol and NaHCO₃ (0.7 g, 8.35 mmol) in 2-propanol. The reaction mixture was refluxed for 8 h. Then reaction was monitored by TLC (CHCl₃ and ethylacetate). The solid obtained on cooling was filtered, washed with chloroform and methanol. Colourless chunks of (I) were grown from an acetone DMF mixture by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids.
	Fig. 2. Packing diagram for (I) showing the intermolecular and intramolecular hydrogen bonding using dashed lines. The hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

4-[(2,5-Dimethylanilino)acetyl]-3,4-dihydroquinoxalin-2(1H)-one top

Crystal data top

C₁₈H₁₉N₃O₂	Z = 2
M_r = 309.36	F(000) = 328
Triclinic, P1	D_x = 1.325 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3806 (2) Å	Cell parameters from 3605 reflections
b = 12.3580 (6) Å	θ = 3.1–25.1°
c = 13.2812 (6) Å	µ = 0.09 mm⁻¹
α = 62.878 (2)°	T = 296 K
β = 84.135 (2)°	Chunk, colourless
γ = 80.835 (3)°	0.38 × 0.17 × 0.06 mm
V = 775.53 (6) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3803 independent reflections
Radiation source: fine-focus sealed tube	2277 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 28.3°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→7
T_min = 0.967, T_max = 0.995	k = −16→16
16710 measured reflections	l = −17→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0583P)² + 0.1485P] where P = (F_o² + 2F_c²)/3
3803 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₉N₃O₂	γ = 80.835 (3)°
M_r = 309.36	V = 775.53 (6) Å³
Triclinic, P1	Z = 2
a = 5.3806 (2) Å	Mo Kα radiation
b = 12.3580 (6) Å	µ = 0.09 mm⁻¹
c = 13.2812 (6) Å	T = 296 K
α = 62.878 (2)°	0.38 × 0.17 × 0.06 mm
β = 84.135 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3803 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2277 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.995	R_int = 0.032
16710 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.21 e Å⁻³
3803 reflections	Δρ_min = −0.17 e Å⁻³
216 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.3267 (3)	−0.03248 (15)	0.21118 (13)	0.0375 (4)
C2	0.2304 (3)	−0.09075 (17)	0.15875 (15)	0.0474 (4)
H2	0.2528	−0.0632	0.0809	0.057*
C3	0.1012 (4)	−0.18983 (18)	0.22234 (17)	0.0565 (5)
H3	0.0350	−0.2283	0.1870	0.068*
C4	0.0695 (4)	−0.23204 (18)	0.33759 (17)	0.0595 (5)
H4	−0.0191	−0.2984	0.3798	0.071*
C5	0.1690 (3)	−0.17607 (17)	0.39049 (15)	0.0527 (5)
H5	0.1486	−0.2050	0.4685	0.063*
C6	0.2993 (3)	−0.07679 (15)	0.32755 (13)	0.0402 (4)
C7	0.5923 (3)	0.04788 (16)	0.33477 (14)	0.0432 (4)
C8	0.6625 (3)	0.07691 (18)	0.21398 (13)	0.0478 (5)
H8A	0.7148	0.1581	0.1760	0.057*
H8B	0.8051	0.0190	0.2119	0.057*
C9	0.3822 (3)	0.16519 (16)	0.05055 (13)	0.0394 (4)
C10	0.5334 (3)	0.27254 (16)	−0.00272 (13)	0.0441 (4)
H10A	0.5118	0.3170	0.0424	0.053*
H10B	0.7110	0.2433	−0.0060	0.053*
C11	0.5571 (3)	0.45478 (16)	−0.18728 (14)	0.0446 (4)
C12	0.4976 (3)	0.51241 (17)	−0.30190 (15)	0.0487 (4)
C13	0.6002 (4)	0.61824 (19)	−0.37152 (17)	0.0605 (5)
H13	0.5629	0.6575	−0.4478	0.073*
C14	0.7563 (4)	0.66854 (19)	−0.33251 (18)	0.0630 (6)
H14	0.8178	0.7415	−0.3819	0.076*
C15	0.8211 (3)	0.61092 (17)	−0.22080 (17)	0.0521 (5)
C16	0.7209 (3)	0.50364 (17)	−0.14910 (15)	0.0487 (4)
H16	0.7643	0.4633	−0.0735	0.058*
C17	0.9978 (4)	0.6614 (2)	−0.1771 (2)	0.0713 (6)
H17A	0.9490	0.6454	−0.1005	0.107*
H17B	0.9907	0.7483	−0.2235	0.107*
H17C	1.1664	0.6229	−0.1795	0.107*
C18	0.3267 (4)	0.4598 (2)	−0.34590 (16)	0.0609 (5)
H18A	0.3982	0.3782	−0.3324	0.091*
H18B	0.3080	0.5101	−0.4257	0.091*
H18C	0.1648	0.4573	−0.3077	0.091*
N1	0.4033 (3)	−0.02041 (14)	0.38128 (12)	0.0479 (4)
N2	0.4571 (2)	0.07258 (12)	0.15222 (11)	0.0388 (3)
N3	0.4475 (3)	0.35148 (15)	−0.11433 (13)	0.0580 (5)
O1	0.7078 (2)	0.08343 (13)	0.38634 (10)	0.0589 (4)
O2	0.2018 (2)	0.16278 (12)	0.00335 (10)	0.0550 (4)
H1N	0.366 (4)	−0.0432 (18)	0.4561 (19)	0.066*
H2N	0.339 (4)	0.3255 (19)	−0.1377 (17)	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0355 (8)	0.0409 (9)	0.0372 (9)	−0.0074 (7)	−0.0020 (6)	−0.0174 (7)
C2	0.0535 (10)	0.0532 (11)	0.0437 (10)	−0.0114 (8)	−0.0022 (8)	−0.0272 (9)
C3	0.0680 (12)	0.0528 (11)	0.0600 (12)	−0.0194 (10)	−0.0072 (9)	−0.0305 (10)
C4	0.0696 (13)	0.0527 (12)	0.0557 (12)	−0.0274 (10)	−0.0070 (10)	−0.0167 (10)
C5	0.0595 (11)	0.0560 (12)	0.0393 (10)	−0.0209 (9)	−0.0047 (8)	−0.0137 (9)
C6	0.0400 (9)	0.0454 (10)	0.0383 (9)	−0.0101 (7)	−0.0055 (7)	−0.0191 (8)
C7	0.0443 (9)	0.0476 (10)	0.0390 (9)	−0.0101 (8)	−0.0091 (7)	−0.0175 (8)
C8	0.0396 (9)	0.0648 (12)	0.0395 (10)	−0.0183 (8)	−0.0044 (7)	−0.0194 (9)
C9	0.0400 (9)	0.0481 (10)	0.0342 (9)	−0.0092 (7)	−0.0001 (7)	−0.0211 (8)
C10	0.0457 (9)	0.0514 (11)	0.0371 (9)	−0.0142 (8)	−0.0029 (7)	−0.0187 (8)
C11	0.0459 (10)	0.0438 (10)	0.0424 (10)	−0.0066 (8)	−0.0030 (7)	−0.0173 (8)
C12	0.0508 (10)	0.0496 (11)	0.0418 (10)	−0.0020 (8)	−0.0040 (8)	−0.0181 (8)
C13	0.0656 (13)	0.0581 (12)	0.0431 (11)	−0.0049 (10)	−0.0028 (9)	−0.0106 (9)
C14	0.0669 (13)	0.0493 (12)	0.0608 (13)	−0.0165 (10)	0.0107 (10)	−0.0142 (10)
C15	0.0487 (10)	0.0501 (11)	0.0614 (12)	−0.0123 (8)	0.0078 (9)	−0.0284 (10)
C16	0.0520 (10)	0.0515 (11)	0.0437 (10)	−0.0136 (9)	−0.0019 (8)	−0.0200 (9)
C17	0.0663 (13)	0.0734 (15)	0.0898 (17)	−0.0316 (11)	0.0121 (12)	−0.0459 (13)
C18	0.0656 (12)	0.0696 (14)	0.0475 (11)	−0.0066 (10)	−0.0132 (9)	−0.0247 (10)
N1	0.0548 (9)	0.0629 (10)	0.0327 (8)	−0.0240 (8)	0.0006 (6)	−0.0224 (7)
N2	0.0381 (7)	0.0471 (8)	0.0331 (7)	−0.0131 (6)	−0.0024 (5)	−0.0169 (6)
N3	0.0679 (11)	0.0545 (10)	0.0456 (9)	−0.0250 (8)	−0.0165 (8)	−0.0090 (8)
O1	0.0667 (8)	0.0757 (9)	0.0453 (7)	−0.0334 (7)	−0.0050 (6)	−0.0283 (7)
O2	0.0546 (7)	0.0619 (8)	0.0449 (7)	−0.0206 (6)	−0.0148 (6)	−0.0140 (6)

Geometric parameters (Å, º) top

C1—C6	1.385 (2)	C10—H10A	0.9700
C1—C2	1.386 (2)	C10—H10B	0.9700
C1—N2	1.4290 (19)	C11—N3	1.383 (2)
C2—C3	1.380 (2)	C11—C16	1.392 (2)
C2—H2	0.9300	C11—C12	1.402 (2)
C3—C4	1.375 (3)	C12—C13	1.376 (3)
C3—H3	0.9300	C12—C18	1.502 (2)
C4—C5	1.377 (2)	C13—C14	1.382 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.384 (2)	C14—C15	1.376 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—N1	1.402 (2)	C15—C16	1.388 (2)
C7—O1	1.2233 (18)	C15—C17	1.504 (3)
C7—N1	1.341 (2)	C16—H16	0.9300
C7—C8	1.496 (2)	C17—H17A	0.9600
C8—N2	1.4632 (18)	C17—H17B	0.9600
C8—H8A	0.9700	C17—H17C	0.9600
C8—H8B	0.9700	C18—H18A	0.9600
C9—O2	1.2192 (17)	C18—H18B	0.9600
C9—N2	1.361 (2)	C18—H18C	0.9600
C9—C10	1.514 (2)	N1—H1N	0.91 (2)
C10—N3	1.429 (2)	N3—H2N	0.85 (2)

C6—C1—C2	119.61 (15)	C16—C11—C12	119.56 (16)
C6—C1—N2	116.51 (13)	C13—C12—C11	117.64 (17)
C2—C1—N2	123.89 (15)	C13—C12—C18	121.72 (17)
C3—C2—C1	119.81 (16)	C11—C12—C18	120.64 (16)
C3—C2—H2	120.1	C12—C13—C14	122.58 (18)
C1—C2—H2	120.1	C12—C13—H13	118.7
C4—C3—C2	120.47 (16)	C14—C13—H13	118.7
C4—C3—H3	119.8	C15—C14—C13	120.20 (18)
C2—C3—H3	119.8	C15—C14—H14	119.9
C3—C4—C5	120.01 (17)	C13—C14—H14	119.9
C3—C4—H4	120.0	C14—C15—C16	118.20 (17)
C5—C4—H4	120.0	C14—C15—C17	121.24 (18)
C4—C5—C6	119.99 (17)	C16—C15—C17	120.56 (18)
C4—C5—H5	120.0	C15—C16—C11	121.77 (17)
C6—C5—H5	120.0	C15—C16—H16	119.1
C5—C6—C1	120.08 (15)	C11—C16—H16	119.1
C5—C6—N1	120.15 (15)	C15—C17—H17A	109.5
C1—C6—N1	119.77 (14)	C15—C17—H17B	109.5
O1—C7—N1	123.53 (16)	H17A—C17—H17B	109.5
O1—C7—C8	120.51 (15)	C15—C17—H17C	109.5
N1—C7—C8	115.94 (14)	H17A—C17—H17C	109.5
N2—C8—C7	113.34 (13)	H17B—C17—H17C	109.5
N2—C8—H8A	108.9	C12—C18—H18A	109.5
C7—C8—H8A	108.9	C12—C18—H18B	109.5
N2—C8—H8B	108.9	H18A—C18—H18B	109.5
C7—C8—H8B	108.9	C12—C18—H18C	109.5
H8A—C8—H8B	107.7	H18A—C18—H18C	109.5
O2—C9—N2	122.03 (15)	H18B—C18—H18C	109.5
O2—C9—C10	120.83 (15)	C7—N1—C6	122.90 (15)
N2—C9—C10	117.14 (13)	C7—N1—H1N	116.9 (12)
N3—C10—C9	108.72 (12)	C6—N1—H1N	118.9 (12)
N3—C10—H10A	109.9	C9—N2—C1	122.08 (12)
C9—C10—H10A	109.9	C9—N2—C8	123.03 (13)
N3—C10—H10B	109.9	C1—N2—C8	114.71 (13)
C9—C10—H10B	109.9	C11—N3—C10	122.78 (14)
H10A—C10—H10B	108.3	C11—N3—H2N	120.7 (14)
N3—C11—C16	121.54 (16)	C10—N3—H2N	115.9 (14)
N3—C11—C12	118.89 (16)

C6—C1—C2—C3	2.1 (3)	C13—C14—C15—C17	177.88 (19)
N2—C1—C2—C3	−178.28 (16)	C14—C15—C16—C11	−0.6 (3)
C1—C2—C3—C4	−0.7 (3)	C17—C15—C16—C11	−179.95 (17)
C2—C3—C4—C5	−0.6 (3)	N3—C11—C16—C15	−176.58 (18)
C3—C4—C5—C6	0.5 (3)	C12—C11—C16—C15	2.3 (3)
C4—C5—C6—C1	0.9 (3)	O1—C7—N1—C6	−169.54 (17)
C4—C5—C6—N1	−179.29 (17)	C8—C7—N1—C6	8.9 (3)
C2—C1—C6—C5	−2.2 (3)	C5—C6—N1—C7	158.51 (17)
N2—C1—C6—C5	178.14 (15)	C1—C6—N1—C7	−21.7 (3)
C2—C1—C6—N1	178.03 (16)	O2—C9—N2—C1	−1.1 (3)
N2—C1—C6—N1	−1.6 (2)	C10—C9—N2—C1	179.09 (14)
O1—C7—C8—N2	−157.17 (17)	O2—C9—N2—C8	−175.90 (16)
N1—C7—C8—N2	24.4 (2)	C10—C9—N2—C8	4.3 (2)
O2—C9—C10—N3	−7.3 (2)	C6—C1—N2—C9	−140.30 (16)
N2—C9—C10—N3	172.49 (15)	C2—C1—N2—C9	40.0 (2)
N3—C11—C12—C13	177.03 (18)	C6—C1—N2—C8	34.9 (2)
C16—C11—C12—C13	−1.9 (3)	C2—C1—N2—C8	−144.75 (17)
N3—C11—C12—C18	−2.7 (3)	C7—C8—N2—C9	129.03 (17)
C16—C11—C12—C18	178.41 (17)	C7—C8—N2—C1	−46.1 (2)
C11—C12—C13—C14	−0.2 (3)	C16—C11—N3—C10	−14.3 (3)
C18—C12—C13—C14	179.55 (19)	C12—C11—N3—C10	166.82 (18)
C12—C13—C14—C15	1.9 (3)	C9—C10—N3—C11	−176.65 (17)
C13—C14—C15—C16	−1.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2N···O2	0.85 (2)	2.20 (2)	2.620 (2)	110.0 (16)
N1—H1N···O1ⁱ	0.91 (2)	1.93 (2)	2.8405 (19)	176.9 (18)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₃O₂
M_r	309.36
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.3806 (2), 12.3580 (6), 13.2812 (6)
α, β, γ (°)	62.878 (2), 84.135 (2), 80.835 (3)
V (Å³)	775.53 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.17 × 0.06

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.967, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	16710, 3803, 2277
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.02
No. of reflections	3803
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2N···O2	0.85 (2)	2.20 (2)	2.620 (2)	110.0 (16)
N1—H1N···O1ⁱ	0.91 (2)	1.93 (2)	2.8405 (19)	176.9 (18)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

WN acknowledges the Higher Education Commission, Pakistan, for providing funding for this research.

References

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
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Khan, A. S. (2008). Eur. J. Med. Chem. 43, 2040–2044. Web of Science CrossRef PubMed CAS Google Scholar
Miyashiro, J., Woods, K. W., Park, C. H., Liu, X., Shi, Y., Johnson, E. F., Bouska, J. J., Olson, A. M., Luo, Y., Fry, E. H., Giranda, V. L. & Penning, T. D. (2009). Bioorg. Med. Chem. Lett. 19, 4050-4054. Web of Science CrossRef PubMed 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