3-Methoxy­benzohydrazide

Jamal, R.A.; Ashiq, U.; Arshad, M.N.; Maqsood, Z.T.; Khan, I.U.

doi:10.1107/S1600536809036526

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2473

doi:10.1107/S1600536809036526

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3-Methoxybenzohydrazide

Rifat Ara Jamal,^a ^* Uzma Ashiq,^a Muhammad Nadeem Arshad,^b Zahida Tasneem Maqsood ^a and Islam Ullah Khan ^b

^aDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: rifat_jamal@yahoo.com

(Received 6 September 2009; accepted 9 September 2009; online 16 September 2009)

The title compound, C₈H₁₀N₂O₂, crystallizes with two independent molecules in an asymmetric unit. The structure is stabilized by nine intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Ashiq, Jamal et al. (2008 , 2009a ,b ); Jamal et al. (2008 , 2009 ); Kallel et al. (1992 ); Saraogi et al. (2002 ). For the biological activity of hydrazides, see: Ara et al. (2007 ); Ashiq, Ara et al. (2008 ).

Experimental

Crystal data

C₈H₁₀N₂O₂
M_r = 166.18
Monoclinic, P 2₁ /n
a = 13.1288 (8) Å
b = 7.5417 (4) Å
c = 17.0734 (10) Å
β = 92.857 (3)°
V = 1688.40 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.39 × 0.15 × 0.11 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.979, T_max = 0.990
18386 measured reflections
4200 independent reflections
1708 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.126
S = 0.95
4200 reflections
237 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11N⋯N12ⁱ	0.91 (2)	2.12 (2)	2.958 (2)	153.3 (18)
N11—H11N⋯N11ⁱ	0.91 (2)	2.63 (2)	3.191 (2)	120.9 (13)
N12—H12N⋯O11ⁱⁱ	0.95 (2)	2.30 (2)	3.193 (2)	155.2 (18)
N12—H13N⋯N22ⁱⁱⁱ	0.85 (2)	2.47 (2)	3.185 (3)	142.6 (19)
N21—H21N⋯O11^iv	0.87 (2)	1.99 (2)	2.860 (2)	172 (2)
N22—H23N⋯O21^v	0.88 (2)	2.14 (2)	3.007 (2)	168 (2)
C18—H18C⋯O21^vi	0.96	2.58	3.498 (3)	160
C22—H22⋯O11^iv	0.93	2.35	3.208 (3)	153
C26—H26⋯O21^vii	0.93	2.56	3.439 (3)	157
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2; (iii) x, y-1, z+1; (iv) x, y+1, z-1; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) -x+1, -y+1, -z+1; (vii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536809036526/pv2207sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036526/pv2207Isup2.hkl

checkCIF report

Comment top

Hydrazides constitute an important class of biologically active organic compounds (Ashiq, Ara et al., 2008; Ara et al., 2007). In searching for biologically active compounds we have synthesized the title compound, (I), and report its crystal structure in this paper.

The asymmetric unit of the title compound contains two crystallographically unique molecules (Fig. 1). The bond distances and bond angles in (I) are similar to the corresponding distances and angles reported in the structures of benzhydrazide (Kallel et al., 1992), para-chloro (Saraogi et al., 2002), para-bromo (Ashiq, Jamal et al., 2008),para-iodo (Jamal et al., 2008), para-methoxy (Ashiq, Jamal et al., 2009a), para-hydroxy (Jamal et al., 2009) and para-phenylsemicarbazide (Ashiq, Jamal et al., 2009b) analogues of (I).

In the crystal structure the molecules are held together by intermolecular hydrogen bonds of the types N—H···N, N—H···O and C—H···O (Table 1 and Fig. 2).

The title compound was found to be active against DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging and inactive against α-glucosidase enzyme (Ashiq, Ara et al., 2008).

Related literature top

For related structures, see: Ashiq, Jamal et al. (2008, 2009a,b); Jamal et al. (2008, 2009); Kallel et al. (1992); Saraogi et al. (2002). For the biological activity of hydrazides, see: Ara et al. (2007); Ashiq, Ara et al. (2008).

Experimental top

All reagent-grade chemicals were obtained from Aldrich and Sigma Chemical companies and were used without further purification. To a solution of ethyl-3-methoxybenzoate (3.6 g, 20 mmol) in 75 ml ethanol, hydrazine hydrate (5.0 ml, 100 mmol) was added. The mixture was refluxed for 5 h and a solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with hexane to afford (I) (yield 79%). Crystal of the title compound suitable for X-ray crystallographic study were grown from a solution of methanol 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 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP diagram of the title compound with the ellipsoids drawn at the 50% probability level, showing the atomic labels.
	Fig. 2. A unit cell packing diagram of (I) showing hydrogen bonds drawn by dashed lines. Hydrogen atoms not involved in H-bonding have been omitted.

3-Methoxybenzohydrazide top

Crystal data top

C₈H₁₀N₂O₂	F(000) = 704
M_r = 166.18	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2161 reflections
a = 13.1288 (8) Å	θ = 3.3–20.5°
b = 7.5417 (4) Å	µ = 0.10 mm⁻¹
c = 17.0734 (10) Å	T = 296 K
β = 92.857 (3)°	Needle, colourless
V = 1688.40 (17) Å³	0.39 × 0.15 × 0.11 mm
Z = 8

Data collection top

Bruker KAPPA APEXII CCD diffractometer	4200 independent reflections
Radiation source: fine-focus sealed tube	1708 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
T_min = 0.979, T_max = 0.990	k = −9→10
18386 measured reflections	l = −22→22

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0499P)²] where P = (F_o² + 2F_c²)/3
4200 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₈H₁₀N₂O₂	V = 1688.40 (17) Å³
M_r = 166.18	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.1288 (8) Å	µ = 0.10 mm⁻¹
b = 7.5417 (4) Å	T = 296 K
c = 17.0734 (10) Å	0.39 × 0.15 × 0.11 mm
β = 92.857 (3)°

Data collection top

Bruker KAPPA APEXII CCD diffractometer	4200 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1708 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.990	R_int = 0.066
18386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.15 e Å⁻³
4200 reflections	Δρ_min = −0.22 e Å⁻³
237 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
O11	0.43146 (11)	0.04300 (19)	1.07269 (9)	0.0607 (5)
O12	0.08143 (12)	0.4522 (2)	0.92286 (10)	0.0767 (5)
N11	0.45156 (14)	0.3134 (2)	1.02178 (10)	0.0459 (5)
H11N	0.4261 (15)	0.422 (3)	1.0077 (12)	0.055*
N12	0.55933 (15)	0.3117 (2)	1.02887 (13)	0.0525 (5)
H12N	0.5835 (16)	0.216 (3)	0.9985 (12)	0.063*
H13N	0.5782 (17)	0.271 (3)	1.0737 (13)	0.063*
C11	0.28175 (15)	0.1986 (2)	1.03161 (12)	0.0406 (5)
C12	0.23758 (16)	0.3243 (3)	0.98111 (12)	0.0470 (6)
H12	0.2785	0.4009	0.9538	0.056*
C13	0.13289 (18)	0.3352 (3)	0.97163 (13)	0.0532 (6)
C14	0.07247 (18)	0.2229 (3)	1.01231 (15)	0.0646 (7)
H14	0.0018	0.2306	1.0059	0.078*
C15	0.11629 (19)	0.0994 (3)	1.06246 (15)	0.0676 (7)
H15	0.0751	0.0245	1.0904	0.081*
C16	0.22077 (18)	0.0856 (3)	1.07168 (13)	0.0545 (6)
H16	0.2500	0.0001	1.1049	0.065*
C17	0.39396 (16)	0.1793 (3)	1.04354 (12)	0.0415 (5)
C18	0.1395 (2)	0.5781 (4)	0.88291 (17)	0.0981 (11)
H18A	0.1783	0.6490	0.9204	0.147*
H18B	0.0946	0.6531	0.8516	0.147*
H18C	0.1850	0.5177	0.8496	0.147*
O21	0.72052 (11)	0.73719 (17)	0.21668 (8)	0.0534 (4)
O22	0.27188 (11)	0.6456 (2)	0.17438 (10)	0.0692 (5)
N21	0.61560 (13)	0.9272 (2)	0.15351 (11)	0.0471 (5)
H21N	0.5565 (16)	0.954 (3)	0.1308 (12)	0.057*
N22	0.69253 (15)	1.0512 (3)	0.13927 (12)	0.0531 (6)
H23N	0.7151 (16)	1.092 (3)	0.1850 (13)	0.064*
H22N	0.7419 (17)	0.994 (3)	0.1205 (14)	0.064*
C21	0.54632 (15)	0.6517 (2)	0.20011 (11)	0.0372 (5)
C22	0.44617 (16)	0.7004 (3)	0.18400 (12)	0.0442 (5)
H22	0.4313	0.8147	0.1665	0.053*
C23	0.36779 (16)	0.5814 (3)	0.19354 (12)	0.0460 (5)
C24	0.38825 (17)	0.4133 (3)	0.21999 (13)	0.0553 (6)
H24	0.3357	0.3330	0.2268	0.066*
C25	0.48845 (19)	0.3654 (3)	0.23633 (14)	0.0640 (7)
H25	0.5030	0.2514	0.2543	0.077*
C26	0.56714 (17)	0.4813 (3)	0.22674 (13)	0.0523 (6)
H26	0.6341	0.4459	0.2380	0.063*
C27	0.63403 (16)	0.7742 (3)	0.19120 (11)	0.0382 (5)
C28	0.18800 (17)	0.5274 (3)	0.17719 (16)	0.0711 (8)
H28A	0.2005	0.4247	0.1459	0.107*
H28B	0.1272	0.5858	0.1571	0.107*
H28C	0.1796	0.4919	0.2305	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0571 (10)	0.0390 (9)	0.0842 (12)	−0.0005 (8)	−0.0140 (8)	0.0216 (8)
O12	0.0586 (11)	0.0935 (13)	0.0778 (13)	0.0257 (10)	−0.0005 (9)	0.0264 (10)
N11	0.0468 (12)	0.0323 (10)	0.0577 (12)	0.0019 (9)	−0.0059 (9)	0.0088 (9)
N12	0.0491 (13)	0.0412 (11)	0.0660 (15)	0.0008 (9)	−0.0087 (10)	0.0088 (10)
C11	0.0475 (13)	0.0319 (11)	0.0418 (13)	0.0002 (10)	−0.0044 (10)	0.0006 (10)
C12	0.0478 (15)	0.0476 (13)	0.0459 (14)	0.0062 (11)	0.0042 (11)	0.0032 (11)
C13	0.0547 (16)	0.0549 (15)	0.0498 (15)	0.0110 (13)	−0.0008 (12)	0.0053 (12)
C14	0.0481 (15)	0.0648 (17)	0.0801 (19)	−0.0026 (13)	−0.0052 (14)	0.0020 (14)
C15	0.0629 (18)	0.0576 (17)	0.082 (2)	−0.0121 (13)	0.0019 (14)	0.0150 (14)
C16	0.0579 (16)	0.0431 (13)	0.0615 (16)	−0.0066 (12)	−0.0072 (12)	0.0119 (11)
C17	0.0529 (14)	0.0315 (12)	0.0396 (13)	−0.0005 (11)	−0.0035 (10)	0.0026 (10)
C18	0.091 (2)	0.115 (3)	0.091 (2)	0.0472 (19)	0.0296 (18)	0.0613 (19)
O21	0.0428 (9)	0.0515 (10)	0.0644 (11)	0.0025 (7)	−0.0106 (8)	0.0114 (7)
O22	0.0410 (10)	0.0611 (11)	0.1053 (14)	0.0010 (8)	0.0027 (9)	0.0147 (9)
N21	0.0419 (11)	0.0390 (11)	0.0589 (13)	−0.0055 (9)	−0.0130 (9)	0.0077 (9)
N22	0.0564 (14)	0.0431 (12)	0.0585 (14)	−0.0114 (10)	−0.0096 (11)	0.0018 (10)
C21	0.0444 (13)	0.0347 (12)	0.0323 (12)	0.0042 (10)	−0.0003 (9)	−0.0027 (9)
C22	0.0490 (14)	0.0359 (12)	0.0479 (14)	0.0050 (11)	0.0030 (11)	0.0044 (10)
C23	0.0449 (14)	0.0453 (13)	0.0481 (14)	0.0048 (11)	0.0042 (11)	−0.0009 (10)
C24	0.0577 (17)	0.0415 (14)	0.0666 (16)	−0.0048 (11)	0.0038 (13)	0.0016 (12)
C25	0.0660 (18)	0.0361 (13)	0.089 (2)	0.0054 (13)	−0.0042 (14)	0.0130 (12)
C26	0.0491 (14)	0.0396 (13)	0.0670 (16)	0.0040 (11)	−0.0073 (12)	0.0050 (11)
C27	0.0451 (14)	0.0350 (12)	0.0339 (12)	0.0035 (10)	−0.0039 (10)	−0.0040 (9)
C28	0.0483 (16)	0.0705 (18)	0.095 (2)	−0.0070 (13)	0.0064 (14)	−0.0227 (15)

Geometric parameters (Å, º) top

O11—C17	1.234 (2)	O21—C27	1.228 (2)
O12—C13	1.368 (3)	O22—C23	1.373 (2)
O12—C18	1.415 (3)	O22—C28	1.419 (2)
N11—C17	1.327 (2)	N21—C27	1.337 (2)
N11—N12	1.414 (2)	N21—N22	1.407 (2)
N11—H11N	0.91 (2)	N21—H21N	0.87 (2)
N12—H12N	0.95 (2)	N22—H23N	0.88 (2)
N12—H13N	0.85 (2)	N22—H22N	0.85 (2)
C11—C16	1.374 (3)	C21—C22	1.380 (3)
C11—C12	1.389 (3)	C21—C26	1.385 (3)
C11—C17	1.484 (3)	C21—C27	1.490 (3)
C12—C13	1.378 (3)	C22—C23	1.381 (3)
C12—H12	0.9300	C22—H22	0.9300
C13—C14	1.372 (3)	C23—C24	1.368 (3)
C14—C15	1.372 (3)	C24—C25	1.379 (3)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.377 (3)	C25—C26	1.369 (3)
C15—H15	0.9300	C25—H25	0.9300
C16—H16	0.9300	C26—H26	0.9300
C18—H18A	0.9600	C28—H28A	0.9600
C18—H18B	0.9600	C28—H28B	0.9600
C18—H18C	0.9600	C28—H28C	0.9600

C13—O12—C18	117.70 (18)	C23—O22—C28	118.35 (18)
C17—N11—N12	123.42 (17)	C27—N21—N22	122.87 (18)
C17—N11—H11N	123.5 (13)	C27—N21—H21N	123.3 (13)
N12—N11—H11N	112.5 (13)	N22—N21—H21N	113.5 (13)
N11—N12—H12N	108.7 (13)	N21—N22—H23N	107.0 (15)
N11—N12—H13N	109.0 (15)	N21—N22—H22N	107.2 (15)
H12N—N12—H13N	97.3 (19)	H23N—N22—H22N	106 (2)
C16—C11—C12	119.8 (2)	C22—C21—C26	118.87 (19)
C16—C11—C17	118.03 (18)	C22—C21—C27	123.24 (18)
C12—C11—C17	122.19 (19)	C26—C21—C27	117.88 (18)
C13—C12—C11	119.8 (2)	C21—C22—C23	120.78 (19)
C13—C12—H12	120.1	C21—C22—H22	119.6
C11—C12—H12	120.1	C23—C22—H22	119.6
O12—C13—C14	115.2 (2)	C24—C23—O22	124.6 (2)
O12—C13—C12	124.7 (2)	C24—C23—C22	120.4 (2)
C14—C13—C12	120.1 (2)	O22—C23—C22	115.02 (19)
C15—C14—C13	120.0 (2)	C23—C24—C25	118.6 (2)
C15—C14—H14	120.0	C23—C24—H24	120.7
C13—C14—H14	120.0	C25—C24—H24	120.7
C14—C15—C16	120.5 (2)	C26—C25—C24	121.8 (2)
C14—C15—H15	119.8	C26—C25—H25	119.1
C16—C15—H15	119.8	C24—C25—H25	119.1
C11—C16—C15	119.9 (2)	C25—C26—C21	119.6 (2)
C11—C16—H16	120.1	C25—C26—H26	120.2
C15—C16—H16	120.1	C21—C26—H26	120.2
O11—C17—N11	121.8 (2)	O21—C27—N21	120.57 (19)
O11—C17—C11	120.67 (18)	O21—C27—C21	121.92 (18)
N11—C17—C11	117.55 (17)	N21—C27—C21	117.51 (18)
O12—C18—H18A	109.5	O22—C28—H28A	109.5
O12—C18—H18B	109.5	O22—C28—H28B	109.5
H18A—C18—H18B	109.5	H28A—C28—H28B	109.5
O12—C18—H18C	109.5	O22—C28—H28C	109.5
H18A—C18—H18C	109.5	H28A—C28—H28C	109.5
H18B—C18—H18C	109.5	H28B—C28—H28C	109.5

C16—C11—C12—C13	0.1 (3)	C26—C21—C22—C23	−0.5 (3)
C17—C11—C12—C13	179.32 (18)	C27—C21—C22—C23	−179.80 (18)
C18—O12—C13—C14	176.3 (2)	C28—O22—C23—C24	−4.2 (3)
C18—O12—C13—C12	−4.0 (3)	C28—O22—C23—C22	175.51 (19)
C11—C12—C13—O12	−179.2 (2)	C21—C22—C23—C24	0.7 (3)
C11—C12—C13—C14	0.4 (3)	C21—C22—C23—O22	−179.05 (17)
O12—C13—C14—C15	179.5 (2)	O22—C23—C24—C25	179.3 (2)
C12—C13—C14—C15	−0.1 (4)	C22—C23—C24—C25	−0.4 (3)
C13—C14—C15—C16	−0.8 (4)	C23—C24—C25—C26	0.0 (3)
C12—C11—C16—C15	−1.0 (3)	C24—C25—C26—C21	0.1 (4)
C17—C11—C16—C15	179.8 (2)	C22—C21—C26—C25	0.1 (3)
C14—C15—C16—C11	1.3 (4)	C27—C21—C26—C25	179.42 (19)
N12—N11—C17—O11	0.9 (3)	N22—N21—C27—O21	1.5 (3)
N12—N11—C17—C11	−179.15 (17)	N22—N21—C27—C21	−178.00 (18)
C16—C11—C17—O11	16.9 (3)	C22—C21—C27—O21	168.96 (19)
C12—C11—C17—O11	−162.3 (2)	C26—C21—C27—O21	−10.3 (3)
C16—C11—C17—N11	−163.0 (2)	C22—C21—C27—N21	−11.6 (3)
C12—C11—C17—N11	17.8 (3)	C26—C21—C27—N21	169.15 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···N12ⁱ	0.91 (2)	2.12 (2)	2.958 (2)	153.3 (18)
N11—H11N···N11ⁱ	0.91 (2)	2.63 (2)	3.191 (2)	120.9 (13)
N12—H12N···O11ⁱⁱ	0.95 (2)	2.30 (2)	3.193 (2)	155.2 (18)
N12—H13N···N22ⁱⁱⁱ	0.85 (2)	2.47 (2)	3.185 (3)	142.6 (19)
N21—H21N···O11^iv	0.87 (2)	1.99 (2)	2.860 (2)	172 (2)
N22—H23N···O21^v	0.88 (2)	2.14 (2)	3.007 (2)	168 (2)
C18—H18C···O21^vi	0.96	2.58	3.498 (3)	160
C22—H22···O11^iv	0.93	2.35	3.208 (3)	153
C26—H26···O21^vii	0.93	2.56	3.439 (3)	157

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

Experimental details

Crystal data
Chemical formula	C₈H₁₀N₂O₂
M_r	166.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	13.1288 (8), 7.5417 (4), 17.0734 (10)
β (°)	92.857 (3)
V (Å³)	1688.40 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.39 × 0.15 × 0.11

Data collection
Diffractometer	Bruker KAPPA APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.979, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	18386, 4200, 1708
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.126, 0.95
No. of reflections	4200
No. of parameters	237
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···N12ⁱ	0.91 (2)	2.12 (2)	2.958 (2)	153.3 (18)
N11—H11N···N11ⁱ	0.91 (2)	2.63 (2)	3.191 (2)	120.9 (13)
N12—H12N···O11ⁱⁱ	0.95 (2)	2.30 (2)	3.193 (2)	155.2 (18)
N12—H13N···N22ⁱⁱⁱ	0.85 (2)	2.47 (2)	3.185 (3)	142.6 (19)
N21—H21N···O11^iv	0.87 (2)	1.99 (2)	2.860 (2)	172 (2)
N22—H23N···O21^v	0.88 (2)	2.14 (2)	3.007 (2)	168 (2)
C18—H18C···O21^vi	0.96	2.58	3.498 (3)	160
C22—H22···O11^iv	0.93	2.35	3.208 (3)	153
C26—H26···O21^vii	0.93	2.56	3.439 (3)	157

Acknowledgements

The authors thank the Higher Education Commission, Pakistan, for providing the diffractometer at GCU, Lahore, and Bana International for their support in collecting the crystallographic data.

References

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