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

Nasir, W.; Munawar, M.A.; Nadeem, S.; Amjad, R.; Adnan, A.

doi:10.1107/S1600536811008178

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o848

doi:10.1107/S1600536811008178

Open

access

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

Waqar Nasir,^a Munawar Ali Munawar,^a ^* Sohail Nadeem,^a Rana Amjad ^a and Ahmad Adnan ^b

^aInstitute of Chemistry, University of the Punjab, Lahore, Pakistan, and ^bDepartment of Chemistry, GC University, Lahore 54000, Pakistan
^*Correspondence e-mail: munawaralimunawar@yahoo.com

(Received 8 February 2011; accepted 3 March 2011; online 12 March 2011)

In the title compound, C₁₇H₁₆N₂O₂S, the pyrazinone ring is non-planar (r.m.s. deviation = 0.1595 Å), with maximum deviations for the 4-position N atom and the adjacent non-fused-ring C atom of 0.2557 (15) and −0.2118 (16) Å, respectively. The dihedral angle between the benzyl ring and pyrazinone rings is 30.45 (18)°. Intermolecular N—H⋯O hydrogen-bonding interactions forms inversion dimers which lead to eight-membered R₂²(8) ring motifs. The dimers are further connected by C—H⋯O interactions.

Related literature

For the biological activity of quinoxalines, see: Ali et al. (2000 ); Moustafa & Yameda (2001 ). For related structures see: Nasir et al. (2009). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₆N₂O₂S
M_r = 312.38
Orthorhombic, P c c n
a = 13.9502 (8) Å
b = 32.2588 (17) Å
c = 6.9728 (3) Å
V = 3137.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.47 × 0.23 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.906, T_max = 0.985
16363 measured reflections
3892 independent reflections
2412 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.183
S = 1.00
3889 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4ⁱ	0.93	2.60	3.452 (3)	153
C10—H10B⋯O4ⁱ	0.97	2.45	3.202 (3)	134
N2—H1N⋯O3ⁱⁱ	0.85 (3)	2.02 (3)	2.875 (3)	175 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -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 for Windows (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/S1600536811008178/hg2799sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008178/hg2799Isup2.hkl

checkCIF report

Comment top

Annulated pyrazines like quinoxalinones represents an important class of nitrogen containing heterocyclic compounds possessing wide variety of biological and industrial applications. The synthetic and naturally occurring quinoxalines compounds have been reported to show antibacterial (Ali et al., 2000) and antitumor (Moustafa & Yameda, 2001). In the present project we aimed to synthesize novel quinoxalinone derivatives which may have enhanced biological and pharmaceutical application.

The title compound (I) is in continuation of previously published work on the analoguous structure, 4-[(2,5-dimethylanilino)acetyl]-3,4- dihydroquinoxalin-2(1H)-one (II) (Nasir, et al., 2009). The dihedral angle between the aromatic ring (C1/C2/C3/C4/C5/C6) and pyrazinone (C1/C6/N2/C8/C7/N1)is 14.01 (12)°. Unlike (II) no intramolecular hydrogen bonding have been observed in (I). The N—H···O type intermolecular hydrogen bonding developed from the cyclic amido functional group forms the inversion dimers and produce eight membered ring motif R₂²(8) (Bernstein et al., 1995). Another C—H···O type hydrogen bonding interaction connects these dimers to another molecule Fig. 2. The benzyl ring (C12/C13/C14/C15/C16/C17) is oriented at dihedral angle of 14.01 (12)° and 30.45 (18)° with respect to aromatic and pyrazinone rings.

Related literature top

For the biological activity of quinoxalines, see: Ali et al. (2000); Moustafa & Yameda (2001). For related structures see: Nasir et al. (2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a suspension of 4-(chloroacetyl)-3,4-dihydroquinoxalin-2(1H)-2-one (2.0 g, 8.9 mmoles) in absolute ethanol (60 mL) fine powdered sodium bicarbonate (1.5 g, 17.8 mmole) was added along with phenylmethanethiol (1.1 mL, 9.0 mmoles). The reaction mixture was heated under reflux for 8-10 h, the progress of the reaction was monitored by TLC (chloroform:ethyl acetate, 7:3 v/v). The reaction mixture was concentrated to half of the original volume under reduced pressure and the precipitate of the product which formed on cooling was filtered, washed with cold ethanol and recrystallized in ethanol.

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 for Windows (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 labelled diagram of structure of (I) with thermal ellipsoids drawn at the 50% probability level.
	Fig. 2. The unit cell packing diagram of (I) showing the hydrogen bondings with dashed lines.

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

Crystal data top

C₁₇H₁₆N₂O₂S	F(000) = 1312
M_r = 312.38	D_x = 1.322 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2915 reflections
a = 13.9502 (8) Å	θ = 3.2–23.1°
b = 32.2588 (17) Å	µ = 0.22 mm⁻¹
c = 6.9728 (3) Å	T = 296 K
V = 3137.9 (3) Å³	Plate, colorless
Z = 8	0.47 × 0.23 × 0.07 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3892 independent reflections
Radiation source: fine-focus sealed tube	2412 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→17
T_min = 0.906, T_max = 0.985	k = −23→43
16363 measured reflections	l = −9→9

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.108P)² + 0.1052P] where P = (F_o² + 2F_c²)/3
3889 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₆N₂O₂S	V = 3137.9 (3) Å³
M_r = 312.38	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.9502 (8) Å	µ = 0.22 mm⁻¹
b = 32.2588 (17) Å	T = 296 K
c = 6.9728 (3) Å	0.47 × 0.23 × 0.07 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3892 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2412 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.985	R_int = 0.044
16363 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.27 e Å⁻³
3889 reflections	Δρ_min = −0.20 e Å⁻³
203 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
S1	0.67947 (5)	0.701430 (18)	0.13947 (11)	0.0539 (3)
O4	0.77529 (11)	0.61610 (5)	0.1173 (2)	0.0439 (4)
N1	0.63517 (13)	0.58234 (5)	0.0968 (3)	0.0364 (4)
O3	0.63199 (12)	0.50899 (5)	0.4824 (2)	0.0530 (5)
C1	0.47960 (15)	0.55216 (6)	0.1309 (3)	0.0377 (5)
C9	0.69061 (15)	0.61743 (6)	0.0743 (3)	0.0331 (5)
C8	0.60499 (16)	0.52927 (7)	0.3446 (3)	0.0399 (5)
C7	0.67595 (15)	0.54813 (7)	0.2064 (3)	0.0400 (5)
H7A	0.7311	0.5581	0.2775	0.048*
H7B	0.6980	0.5269	0.1184	0.048*
N2	0.51165 (14)	0.53532 (6)	0.3046 (3)	0.0442 (5)
C10	0.64388 (16)	0.65674 (7)	0.0037 (3)	0.0394 (5)
H10A	0.5748	0.6537	0.0112	0.047*
H10B	0.6607	0.6610	−0.1299	0.047*
C5	0.51272 (19)	0.58963 (8)	−0.1586 (4)	0.0490 (6)
H5	0.5557	0.6032	−0.2391	0.059*
C12	0.50134 (19)	0.69134 (8)	0.3071 (4)	0.0514 (6)
C6	0.54236 (15)	0.57563 (6)	0.0199 (3)	0.0364 (5)
C3	0.35632 (19)	0.56161 (9)	−0.1015 (4)	0.0581 (7)
H3	0.2931	0.5579	−0.1402	0.070*
C2	0.38689 (17)	0.54535 (7)	0.0697 (4)	0.0477 (6)
H2	0.3451	0.5297	0.1445	0.057*
C11	0.6058 (2)	0.69568 (9)	0.3512 (4)	0.0577 (7)
H11A	0.6269	0.6714	0.4217	0.069*
H11B	0.6150	0.7197	0.4332	0.069*
C4	0.4191 (2)	0.58341 (8)	−0.2165 (4)	0.0592 (7)
H4	0.3983	0.5940	−0.3334	0.071*
C13	0.4534 (3)	0.65588 (11)	0.3446 (5)	0.0776 (9)
H13	0.4853	0.6339	0.4025	0.093*
C16	0.3583 (3)	0.7183 (2)	0.1691 (9)	0.156 (3)
H16	0.3267	0.7396	0.1054	0.188*
C14	0.3569 (3)	0.65185 (15)	0.2976 (7)	0.1123 (16)
H14	0.3240	0.6275	0.3254	0.135*
C17	0.4533 (2)	0.72278 (13)	0.2194 (7)	0.1095 (15)
H17	0.4849	0.7475	0.1932	0.131*
C15	0.3119 (3)	0.6836 (2)	0.2115 (7)	0.133 (2)
H15	0.2473	0.6812	0.1811	0.160*
H1N	0.471 (2)	0.5207 (9)	0.367 (4)	0.060 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0418 (4)	0.0307 (3)	0.0892 (6)	−0.0038 (2)	0.0018 (3)	−0.0011 (3)
O4	0.0330 (9)	0.0376 (8)	0.0611 (10)	−0.0068 (7)	−0.0027 (7)	0.0045 (7)
N1	0.0310 (10)	0.0358 (10)	0.0424 (10)	−0.0056 (8)	−0.0005 (8)	0.0066 (8)
O3	0.0451 (10)	0.0577 (11)	0.0561 (11)	−0.0119 (8)	−0.0068 (8)	0.0193 (9)
C1	0.0321 (11)	0.0339 (11)	0.0473 (13)	−0.0016 (9)	0.0012 (10)	0.0006 (10)
C9	0.0322 (11)	0.0316 (10)	0.0356 (11)	−0.0031 (9)	0.0043 (9)	−0.0004 (9)
C8	0.0380 (12)	0.0360 (11)	0.0456 (13)	−0.0075 (10)	0.0005 (10)	0.0048 (10)
C7	0.0315 (11)	0.0358 (11)	0.0527 (13)	−0.0028 (9)	0.0015 (10)	0.0092 (10)
N2	0.0336 (11)	0.0494 (11)	0.0495 (12)	−0.0061 (9)	0.0057 (9)	0.0140 (10)
C10	0.0355 (12)	0.0381 (12)	0.0447 (12)	−0.0009 (10)	0.0063 (10)	0.0042 (10)
C5	0.0462 (15)	0.0544 (15)	0.0464 (14)	−0.0109 (12)	−0.0015 (11)	0.0093 (11)
C12	0.0476 (15)	0.0572 (15)	0.0495 (14)	0.0108 (12)	0.0027 (11)	−0.0060 (12)
C6	0.0302 (11)	0.0332 (10)	0.0459 (12)	−0.0037 (9)	−0.0009 (9)	−0.0002 (9)
C3	0.0391 (13)	0.0587 (16)	0.0765 (19)	−0.0109 (13)	−0.0155 (13)	−0.0009 (14)
C2	0.0338 (12)	0.0452 (13)	0.0642 (16)	−0.0086 (11)	0.0019 (11)	0.0022 (12)
C11	0.0540 (17)	0.0592 (16)	0.0599 (16)	0.0099 (13)	−0.0070 (13)	−0.0154 (13)
C4	0.0557 (17)	0.0663 (17)	0.0558 (16)	−0.0097 (14)	−0.0181 (13)	0.0063 (13)
C13	0.068 (2)	0.075 (2)	0.090 (2)	−0.0013 (18)	0.0167 (18)	−0.0014 (18)
C16	0.062 (3)	0.211 (6)	0.197 (6)	0.044 (3)	0.011 (3)	0.093 (5)
C14	0.076 (3)	0.135 (4)	0.126 (4)	−0.044 (3)	0.031 (3)	−0.041 (3)
C17	0.053 (2)	0.099 (3)	0.176 (4)	0.028 (2)	0.007 (2)	0.054 (3)
C15	0.050 (2)	0.241 (7)	0.109 (4)	0.011 (3)	−0.010 (2)	−0.007 (4)

Geometric parameters (Å, º) top

S1—C10	1.795 (2)	C5—H5	0.9300
S1—C11	1.808 (3)	C12—C13	1.351 (4)
O4—C9	1.219 (3)	C12—C17	1.361 (4)
N1—C9	1.380 (3)	C12—C11	1.496 (4)
N1—C6	1.418 (3)	C3—C2	1.372 (4)
N1—C7	1.458 (3)	C3—C4	1.380 (4)
O3—C8	1.222 (3)	C3—H3	0.9300
C1—C2	1.380 (3)	C2—H2	0.9300
C1—C6	1.393 (3)	C11—H11A	0.9700
C1—N2	1.400 (3)	C11—H11B	0.9700
C9—C10	1.508 (3)	C4—H4	0.9300
C8—N2	1.346 (3)	C13—C14	1.392 (5)
C8—C7	1.509 (3)	C13—H13	0.9300
C7—H7A	0.9700	C16—C15	1.327 (8)
C7—H7B	0.9700	C16—C17	1.379 (6)
N2—H1N	0.85 (3)	C16—H16	0.9300
C10—H10A	0.9700	C14—C15	1.342 (7)
C10—H10B	0.9700	C14—H14	0.9300
C5—C4	1.382 (4)	C17—H17	0.9300
C5—C6	1.387 (3)	C15—H15	0.9300

C10—S1—C11	101.02 (12)	C5—C6—C1	119.2 (2)
C9—N1—C6	126.45 (18)	C5—C6—N1	124.2 (2)
C9—N1—C7	117.51 (17)	C1—C6—N1	116.55 (19)
C6—N1—C7	116.03 (17)	C2—C3—C4	120.2 (2)
C2—C1—C6	120.3 (2)	C2—C3—H3	119.9
C2—C1—N2	120.3 (2)	C4—C3—H3	119.9
C6—C1—N2	119.4 (2)	C3—C2—C1	120.0 (2)
O4—C9—N1	119.08 (19)	C3—C2—H2	120.0
O4—C9—C10	121.91 (19)	C1—C2—H2	120.0
N1—C9—C10	118.98 (19)	C12—C11—S1	113.29 (19)
O3—C8—N2	122.6 (2)	C12—C11—H11A	108.9
O3—C8—C7	121.0 (2)	S1—C11—H11A	108.9
N2—C8—C7	116.3 (2)	C12—C11—H11B	108.9
N1—C7—C8	112.57 (18)	S1—C11—H11B	108.9
N1—C7—H7A	109.1	H11A—C11—H11B	107.7
C8—C7—H7A	109.1	C3—C4—C5	120.3 (3)
N1—C7—H7B	109.1	C3—C4—H4	119.9
C8—C7—H7B	109.1	C5—C4—H4	119.9
H7A—C7—H7B	107.8	C12—C13—C14	120.8 (4)
C8—N2—C1	123.0 (2)	C12—C13—H13	119.6
C8—N2—H1N	117.0 (19)	C14—C13—H13	119.6
C1—N2—H1N	116.3 (19)	C15—C16—C17	120.0 (5)
C9—C10—S1	112.54 (16)	C15—C16—H16	120.0
C9—C10—H10A	109.1	C17—C16—H16	120.0
S1—C10—H10A	109.1	C15—C14—C13	119.1 (4)
C9—C10—H10B	109.1	C15—C14—H14	120.4
S1—C10—H10B	109.1	C13—C14—H14	120.4
H10A—C10—H10B	107.8	C12—C17—C16	120.7 (4)
C4—C5—C6	119.8 (2)	C12—C17—H17	119.7
C4—C5—H5	120.1	C16—C17—H17	119.7
C6—C5—H5	120.1	C16—C15—C14	121.1 (4)
C13—C12—C17	118.3 (3)	C16—C15—H15	119.5
C13—C12—C11	121.4 (3)	C14—C15—H15	119.5
C17—C12—C11	120.2 (3)

C6—N1—C9—O4	−166.4 (2)	C9—N1—C6—C5	36.4 (3)
C7—N1—C9—O4	12.1 (3)	C7—N1—C6—C5	−142.1 (2)
C6—N1—C9—C10	15.7 (3)	C9—N1—C6—C1	−145.9 (2)
C7—N1—C9—C10	−165.86 (19)	C7—N1—C6—C1	35.6 (3)
C9—N1—C7—C8	136.4 (2)	C4—C3—C2—C1	2.5 (4)
C6—N1—C7—C8	−44.9 (3)	C6—C1—C2—C3	0.2 (4)
O3—C8—C7—N1	−159.2 (2)	N2—C1—C2—C3	−179.4 (2)
N2—C8—C7—N1	22.2 (3)	C13—C12—C11—S1	114.1 (3)
O3—C8—N2—C1	−168.6 (2)	C17—C12—C11—S1	−62.9 (4)
C7—C8—N2—C1	10.0 (3)	C10—S1—C11—C12	−54.1 (2)
C2—C1—N2—C8	158.4 (2)	C2—C3—C4—C5	−1.1 (4)
C6—C1—N2—C8	−21.2 (3)	C6—C5—C4—C3	−3.1 (4)
O4—C9—C10—S1	−43.2 (3)	C17—C12—C13—C14	−1.1 (5)
N1—C9—C10—S1	134.71 (18)	C11—C12—C13—C14	−178.1 (3)
C11—S1—C10—C9	−78.50 (18)	C12—C13—C14—C15	1.0 (6)
C4—C5—C6—C1	5.8 (4)	C13—C12—C17—C16	−0.4 (6)
C4—C5—C6—N1	−176.6 (2)	C11—C12—C17—C16	176.6 (4)
C2—C1—C6—C5	−4.4 (3)	C15—C16—C17—C12	2.1 (9)
N2—C1—C6—C5	175.2 (2)	C17—C16—C15—C14	−2.3 (10)
C2—C1—C6—N1	177.8 (2)	C13—C14—C15—C16	0.7 (8)
N2—C1—C6—N1	−2.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4ⁱ	0.93	2.60	3.452 (3)	153
C10—H10B···O4ⁱ	0.97	2.45	3.202 (3)	134
N2—H1N···O3ⁱⁱ	0.85 (3)	2.02 (3)	2.875 (3)	175 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₂S
M_r	312.38
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	296
a, b, c (Å)	13.9502 (8), 32.2588 (17), 6.9728 (3)
V (Å³)	3137.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.47 × 0.23 × 0.07

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.906, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	16363, 3892, 2412
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.183, 1.00
No. of reflections	3889
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.20

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (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
C5—H5···O4ⁱ	0.93	2.60	3.452 (3)	153
C10—H10B···O4ⁱ	0.97	2.45	3.202 (3)	134
N2—H1N···O3ⁱⁱ	0.85 (3)	2.02 (3)	2.875 (3)	175 (3)

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Pakistan, for providing funding for this research.

References

Ali, A. A., Ismail, M. M. F., El-Gaby, M. S. A., Zahran, M. A. & Ammar, Y. A. (2000). Molecules, 5, 864–873. CrossRef CAS 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
Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Moustafa, O. S. & Yameda, Y. (2001). J. Heterocycl. Chem. 38, 809–811. CrossRef CAS Google Scholar
Nasir, W., Munawar, M. A., Ahmad, S., Nadeem, S. & Shahid, M. (2009). Acta Cryst. E65, o3006. Web of Science CSD CrossRef IUCr Journals 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