4-Phenyl­semicarbazide

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

doi:10.1107/S1600536809035284

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2360

doi:10.1107/S1600536809035284

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4-Phenylsemicarbazide

Uzma Ashiq,^a ^* Rifat Ara Jamal,^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: uzzmma@yahoo.com

(Received 11 August 2009; accepted 1 September 2009; online 5 September 2009)

The title compound, C₇H₉N₃O, crystallizes with two independent molecules per asymmetric unit. The structure is stabilized by four distinct intermolecular N—H⋯O hydrogen bonds. Four intramolecular interactions of the N—H⋯N and C—H⋯O types are also observed.

Related literature

For related structures see: Ashiq, Jamal et al. (2008 , 2009 ); 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

C₇H₉N₃O
M_r = 151.17
Monoclinic, P 2₁ /c
a = 16.5984 (10) Å
b = 8.8862 (4) Å
c = 10.3518 (6) Å
β = 91.359 (3)°
V = 1526.43 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.43 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.979, T_max = 0.990
15394 measured reflections
3500 independent reflections
2258 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.107
S = 1.03
3500 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11N⋯N13	0.849 (16)	2.130 (15)	2.6149 (19)	116.0 (13)
N12—H12N⋯O21ⁱ	0.872 (15)	2.071 (15)	2.9386 (15)	172.8 (14)
N13—H14N⋯O11ⁱⁱ	0.887 (18)	2.383 (17)	3.2149 (18)	156.1 (15)
N21—H21N⋯N23	0.852 (16)	2.130 (17)	2.6093 (19)	115.3 (14)
N22—H22N⋯O11ⁱⁱⁱ	0.901 (16)	2.079 (17)	2.9784 (17)	175.9 (14)
N23—H23N⋯O21^iv	0.919 (17)	2.203 (17)	3.0850 (18)	160.5 (15)
C12—H12⋯O11	0.93	2.33	2.9119 (18)	120
C22—H22⋯O21	0.93	2.46	2.9833 (18)	116
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035284/pk2182sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035284/pk2182Isup2.hkl

checkCIF report

Comment top

Hydrazides are known to have different biological activities (Ashiq, Ara et al., 2008; Ara et al., 2007). In order to study the biological activity of 4-phenylsemicarbazide, we undertook the synthesis of title compound and report its crystal structure in this paper. The title compound was found to be active against urease enzyme (Ara et al., 2007). 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., 2009) and para-hydroxy (Jamal et al., 2009) analogues have already been reported.

The unit cell contains two crystallographically unique molecules, whose molecular structures are presented in Fig. 1. The bond distances and bond angles are similar to the corresponding distances and angles reported in the structures quoted above. The molecular packing diagram (Fig. 2) shows the presence of four intermolecular hydrogen bonds and four intramolecular hydrogen interactions. In the crystal structure, two adjacent molecules are held together by intermolecular hydrogen bonds between the N12—H12N···O21, N13—H14N···O11, N22—H22N···O11 and N23—H23N···O21 (details are given in Table 1).

Related literature top

For related structures see: Ashiq, Jamal et al. (2008, 2009); 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 phenyl urea (34 g, 0.25 moles) in 50 ml ethanol, hydrazine hydrate (25.0 ml, 0.45 moles) was added. The mixture was refluxed for 24 h and solid 4-phenylsemicarbazide was obtained upon removal of the solvent by rotary evaporation (yield 79%).

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 Mercury (Macrae et al., 2006); 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 packing diagram viewed down the c axis showing hydrogen bonds drawn as dashed lines. Hydrogen atoms not involved in H-bonding have been omitted.

4-Phenylsemicarbazide top

Crystal data top

C₇H₉N₃O	F(000) = 640
M_r = 151.17	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3838 reflections
a = 16.5984 (10) Å	θ = 2.5–24.4°
b = 8.8862 (4) Å	µ = 0.09 mm⁻¹
c = 10.3518 (6) Å	T = 296 K
β = 91.359 (3)°	Needle, colourless
V = 1526.43 (14) Å³	0.43 × 0.15 × 0.12 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	3500 independent reflections
Radiation source: fine-focus sealed tube	2258 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→20
T_min = 0.979, T_max = 0.990	k = −6→11
15394 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0459P)² + 0.1614P] where P = (F_o² + 2F_c²)/3
3500 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₇H₉N₃O	V = 1526.43 (14) Å³
M_r = 151.17	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.5984 (10) Å	µ = 0.09 mm⁻¹
b = 8.8862 (4) Å	T = 296 K
c = 10.3518 (6) Å	0.43 × 0.15 × 0.12 mm
β = 91.359 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3500 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2258 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.990	R_int = 0.030
15394 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.16 e Å⁻³
3500 reflections	Δρ_min = −0.15 e Å⁻³
223 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.01604 (6)	0.79747 (12)	0.48141 (10)	0.0553 (4)
N11	0.09359 (7)	0.58992 (13)	0.44101 (12)	0.0427 (4)
N12	−0.01754 (7)	0.64373 (13)	0.31698 (11)	0.0438 (4)
N13	−0.00041 (8)	0.51513 (16)	0.24513 (14)	0.0506 (5)
C11	0.15892 (8)	0.60879 (14)	0.52831 (12)	0.0354 (4)
C12	0.16095 (9)	0.71248 (16)	0.62779 (13)	0.0439 (5)
C13	0.22909 (10)	0.72368 (18)	0.70707 (15)	0.0508 (5)
C14	0.29449 (9)	0.63342 (19)	0.68932 (15)	0.0554 (6)
C15	0.29205 (10)	0.52914 (19)	0.59133 (16)	0.0572 (6)
C16	0.22502 (9)	0.51619 (17)	0.51125 (14)	0.0462 (5)
C17	0.03011 (8)	0.68266 (15)	0.41816 (13)	0.0378 (5)
O21	0.17516 (6)	0.28317 (12)	0.23819 (10)	0.0529 (4)
N21	0.28009 (7)	0.40092 (15)	0.13966 (13)	0.0500 (5)
N22	0.15623 (8)	0.38933 (15)	0.04272 (12)	0.0488 (4)
N23	0.18846 (8)	0.47117 (17)	−0.05959 (13)	0.0514 (5)
C21	0.34464 (8)	0.38042 (16)	0.22790 (14)	0.0433 (5)
C22	0.34917 (9)	0.26384 (18)	0.31535 (15)	0.0509 (5)
C23	0.41651 (9)	0.2490 (2)	0.39537 (16)	0.0593 (6)
C24	0.47943 (10)	0.3476 (2)	0.38889 (17)	0.0643 (6)
C25	0.47515 (10)	0.4626 (2)	0.30239 (18)	0.0707 (7)
C26	0.40834 (9)	0.48014 (19)	0.22223 (17)	0.0596 (6)
C27	0.20285 (8)	0.35311 (15)	0.14604 (14)	0.0405 (5)
H11N	0.0960 (9)	0.5210 (18)	0.3845 (15)	0.0510*
H12	0.11680	0.77440	0.64140	0.0530*
H12N	−0.0624 (9)	0.6927 (17)	0.3025 (14)	0.0530*
H13	0.23030	0.79400	0.77360	0.0610*
H13N	−0.0413 (10)	0.4498 (19)	0.2569 (15)	0.0610*
H14	0.34000	0.64240	0.74280	0.0660*
H14N	0.0017 (10)	0.5393 (19)	0.1621 (17)	0.0610*
H15	0.33610	0.46660	0.57900	0.0690*
H16	0.22410	0.44500	0.44540	0.0550*
H21N	0.2880 (10)	0.4551 (18)	0.0733 (16)	0.0600*
H22	0.30700	0.19530	0.32060	0.0610*
H22N	0.1043 (10)	0.3598 (17)	0.0395 (15)	0.0590*
H23	0.41900	0.17040	0.45470	0.0710*
H23N	0.1844 (10)	0.4143 (19)	−0.1336 (16)	0.0620*
H24	0.52460	0.33620	0.44290	0.0770*
H24N	0.1591 (10)	0.5550 (19)	−0.0679 (15)	0.0620*
H25	0.51780	0.53010	0.29720	0.0850*
H26	0.40610	0.55970	0.16390	0.0720*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0570 (7)	0.0548 (7)	0.0534 (7)	0.0192 (5)	−0.0156 (5)	−0.0142 (5)
N11	0.0424 (7)	0.0419 (7)	0.0434 (7)	0.0079 (6)	−0.0090 (6)	−0.0063 (5)
N12	0.0394 (7)	0.0465 (7)	0.0449 (7)	0.0100 (6)	−0.0088 (6)	−0.0061 (6)
N13	0.0484 (8)	0.0510 (8)	0.0519 (8)	0.0034 (6)	−0.0074 (7)	−0.0105 (7)
C11	0.0355 (7)	0.0362 (7)	0.0345 (7)	−0.0003 (6)	0.0002 (6)	0.0061 (6)
C12	0.0433 (8)	0.0468 (8)	0.0416 (8)	0.0066 (7)	−0.0014 (6)	−0.0018 (7)
C13	0.0546 (10)	0.0539 (9)	0.0435 (9)	−0.0006 (8)	−0.0050 (7)	−0.0052 (7)
C14	0.0438 (9)	0.0679 (11)	0.0537 (10)	0.0002 (8)	−0.0136 (7)	0.0009 (8)
C15	0.0435 (9)	0.0658 (11)	0.0619 (10)	0.0155 (8)	−0.0063 (8)	−0.0005 (8)
C16	0.0438 (8)	0.0480 (9)	0.0464 (9)	0.0087 (7)	−0.0042 (7)	−0.0025 (7)
C17	0.0372 (8)	0.0392 (8)	0.0370 (8)	0.0024 (6)	−0.0014 (6)	0.0032 (6)
O21	0.0386 (6)	0.0680 (7)	0.0520 (7)	−0.0068 (5)	−0.0024 (5)	0.0135 (5)
N21	0.0380 (7)	0.0630 (9)	0.0488 (8)	−0.0090 (6)	−0.0040 (6)	0.0102 (6)
N22	0.0372 (7)	0.0595 (8)	0.0495 (8)	−0.0050 (6)	−0.0050 (6)	0.0095 (6)
N23	0.0517 (8)	0.0591 (9)	0.0432 (8)	0.0001 (6)	−0.0026 (6)	0.0044 (7)
C21	0.0340 (8)	0.0526 (9)	0.0433 (8)	−0.0017 (6)	0.0008 (6)	−0.0063 (7)
C22	0.0384 (8)	0.0566 (10)	0.0578 (10)	−0.0019 (7)	0.0009 (7)	0.0013 (8)
C23	0.0455 (10)	0.0743 (12)	0.0579 (10)	0.0094 (8)	−0.0022 (8)	0.0068 (9)
C24	0.0405 (9)	0.0906 (13)	0.0612 (11)	0.0034 (9)	−0.0121 (8)	−0.0091 (10)
C25	0.0445 (10)	0.0823 (13)	0.0846 (13)	−0.0177 (9)	−0.0116 (9)	−0.0025 (11)
C26	0.0488 (10)	0.0628 (11)	0.0669 (11)	−0.0135 (8)	−0.0044 (8)	0.0043 (8)
C27	0.0355 (8)	0.0419 (8)	0.0440 (8)	−0.0013 (6)	−0.0016 (6)	−0.0033 (7)

Geometric parameters (Å, º) top

O11—C17	1.2375 (17)	C12—C13	1.385 (2)
O21—C27	1.2362 (17)	C13—C14	1.366 (2)
N11—C11	1.4051 (18)	C14—C15	1.374 (2)
N11—C17	1.3541 (18)	C15—C16	1.376 (2)
N12—N13	1.3964 (18)	C12—H12	0.9300
N12—C17	1.3427 (18)	C13—H13	0.9300
N11—H11N	0.849 (16)	C14—H14	0.9300
N12—H12N	0.872 (15)	C15—H15	0.9300
N13—H14N	0.887 (18)	C16—H16	0.9300
N13—H13N	0.904 (17)	C21—C22	1.377 (2)
N21—C21	1.4032 (19)	C21—C26	1.382 (2)
N21—C27	1.3537 (18)	C22—C23	1.382 (2)
N22—C27	1.3443 (19)	C23—C24	1.366 (2)
N22—N23	1.4013 (19)	C24—C25	1.360 (3)
N21—H21N	0.852 (16)	C25—C26	1.378 (2)
N22—H22N	0.901 (16)	C22—H22	0.9300
N23—H23N	0.919 (17)	C23—H23	0.9300
N23—H24N	0.893 (17)	C24—H24	0.9300
C11—C12	1.3817 (19)	C25—H25	0.9300
C11—C16	1.386 (2)	C26—H26	0.9300

C11—N11—C17	128.70 (12)	C13—C12—H12	120.00
N13—N12—C17	120.18 (12)	C14—C13—H13	119.00
C11—N11—H11N	118.8 (10)	C12—C13—H13	119.00
C17—N11—H11N	111.6 (10)	C15—C14—H14	120.00
C17—N12—H12N	119.4 (10)	C13—C14—H14	120.00
N13—N12—H12N	120.0 (10)	C16—C15—H15	120.00
N12—N13—H14N	109.3 (11)	C14—C15—H15	120.00
H13N—N13—H14N	109.5 (15)	C15—C16—H16	120.00
N12—N13—H13N	106.9 (11)	C11—C16—H16	120.00
C21—N21—C27	129.56 (13)	C22—C21—C26	118.72 (14)
N23—N22—C27	120.18 (12)	N21—C21—C22	123.69 (13)
C21—N21—H21N	117.9 (11)	N21—C21—C26	117.53 (13)
C27—N21—H21N	112.4 (11)	C21—C22—C23	119.79 (14)
C27—N22—H22N	119.5 (10)	C22—C23—C24	121.19 (16)
N23—N22—H22N	120.4 (10)	C23—C24—C25	119.10 (16)
H23N—N23—H24N	110.4 (15)	C24—C25—C26	120.69 (16)
N22—N23—H24N	106.8 (10)	C21—C26—C25	120.50 (16)
N22—N23—H23N	108.8 (11)	O21—C27—N21	124.42 (13)
C12—C11—C16	119.04 (13)	O21—C27—N22	121.12 (13)
N11—C11—C16	116.64 (12)	N21—C27—N22	114.46 (13)
N11—C11—C12	124.32 (12)	C21—C22—H22	120.00
C11—C12—C13	119.65 (14)	C23—C22—H22	120.00
C12—C13—C14	121.24 (14)	C22—C23—H23	119.00
C13—C14—C15	119.07 (15)	C24—C23—H23	119.00
C14—C15—C16	120.69 (15)	C23—C24—H24	120.00
C11—C16—C15	120.30 (14)	C25—C24—H24	120.00
N11—C17—N12	114.90 (12)	C24—C25—H25	120.00
O11—C17—N11	124.42 (13)	C26—C25—H25	120.00
O11—C17—N12	120.67 (12)	C21—C26—H26	120.00
C11—C12—H12	120.00	C25—C26—H26	120.00

C17—N11—C11—C12	14.9 (2)	C16—C11—C12—C13	1.0 (2)
C17—N11—C11—C16	−164.97 (14)	N11—C11—C16—C15	178.94 (13)
C11—N11—C17—O11	−6.6 (2)	C11—C12—C13—C14	−0.3 (2)
C11—N11—C17—N12	171.74 (13)	C12—C13—C14—C15	−0.4 (2)
N13—N12—C17—O11	179.06 (13)	C13—C14—C15—C16	0.5 (2)
N13—N12—C17—N11	0.66 (18)	C14—C15—C16—C11	0.2 (2)
C21—N21—C27—O21	2.2 (2)	N21—C21—C22—C23	177.50 (14)
C27—N21—C21—C22	24.3 (2)	C26—C21—C22—C23	0.2 (2)
C27—N21—C21—C26	−158.35 (15)	N21—C21—C26—C25	−177.24 (15)
C21—N21—C27—N22	−178.53 (14)	C22—C21—C26—C25	0.2 (2)
N23—N22—C27—N21	−0.5 (2)	C21—C22—C23—C24	−0.5 (2)
N23—N22—C27—O21	178.77 (13)	C22—C23—C24—C25	0.3 (3)
N11—C11—C12—C13	−178.84 (13)	C23—C24—C25—C26	0.1 (3)
C12—C11—C16—C15	−0.9 (2)	C24—C25—C26—C21	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···N13	0.849 (16)	2.130 (15)	2.6149 (19)	116.0 (13)
N12—H12N···O21ⁱ	0.872 (15)	2.071 (15)	2.9386 (15)	172.8 (14)
N13—H14N···O11ⁱⁱ	0.887 (18)	2.383 (17)	3.2149 (18)	156.1 (15)
N21—H21N···N23	0.852 (16)	2.130 (17)	2.6093 (19)	115.3 (14)
N22—H22N···O11ⁱⁱⁱ	0.901 (16)	2.079 (17)	2.9784 (17)	175.9 (14)
N23—H23N···O21^iv	0.919 (17)	2.203 (17)	3.0850 (18)	160.5 (15)
C12—H12···O11	0.93	2.33	2.9119 (18)	120
C22—H22···O21	0.93	2.46	2.9833 (18)	116

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

Experimental details

Crystal data
Chemical formula	C₇H₉N₃O
M_r	151.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.5984 (10), 8.8862 (4), 10.3518 (6)
β (°)	91.359 (3)
V (Å³)	1526.43 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.15 × 0.12

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	15394, 3500, 2258
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 1.03
No. of reflections	3500
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···N13	0.849 (16)	2.130 (15)	2.6149 (19)	116.0 (13)
N12—H12N···O21ⁱ	0.872 (15)	2.071 (15)	2.9386 (15)	172.8 (14)
N13—H14N···O11ⁱⁱ	0.887 (18)	2.383 (17)	3.2149 (18)	156.1 (15)
N21—H21N···N23	0.852 (16)	2.130 (17)	2.6093 (19)	115.3 (14)
N22—H22N···O11ⁱⁱⁱ	0.901 (16)	2.079 (17)	2.9784 (17)	175.9 (14)
N23—H23N···O21^iv	0.919 (17)	2.203 (17)	3.0850 (18)	160.5 (15)
C12—H12···O11	0.93	2.33	2.9119 (18)	120
C22—H22···O21	0.93	2.46	2.9833 (18)	116

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

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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