N-(3,5-Dichloro­phen­yl)-2-(naphthalen-1-yl)acetamide

Fun, H.-K.; Quah, C.K.; Narayana, B.; Nayak, P.S.; Sarojini, B.K.

doi:10.1107/S1600536811041468

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2941-o2942

doi:10.1107/S1600536811041468

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N-(3,5-Dichlorophenyl)-2-(naphthalen-1-yl)acetamide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § B. Narayana,^b Prakash S. Nayak ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Montepadavu, P.O., Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 3 October 2011; accepted 8 October 2011; online 12 October 2011)

In the title compound, C₁₈H₁₃Cl₂NO, the naphthalene ring system [maximum deviation = 0.038 (4) Å] and the benzene ring form dihedral angles of 69.5 (2) and 37.2 (2)°, respectively, with the essentially planar acetamide unit [maximum deviation = 0.004 (4) Å]. The naphthalene ring system forms a dihedral angle of 52.36 (18)° with the benzene ring. In the crystal, molecules are linked via intermolecular N—H⋯O hydrogen bonds, forming chains along [001].

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ); Mijin et al. (2008 ). For the coordination abilities of amides, see: Wu et al. (2008 , 2010 ). For related structures, see: Fun et al. (2010 , 2011 ); Li & Wu (2010 ); Xiao et al. (2010 ); Praveen et al. (2011 ); Wang et al. (2010 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₃Cl₂NO
M_r = 330.19
Monoclinic, P 2₁ /c
a = 7.8090 (14) Å
b = 24.811 (4) Å
c = 9.6783 (13) Å
β = 125.05 (1)°
V = 1535.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 296 K
0.38 × 0.29 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.855, T_max = 0.974
16035 measured reflections
4453 independent reflections
2621 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.198
S = 1.03
4453 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.80 (4)	2.12 (4)	2.911 (4)	170 (4)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041468/lh5351sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041468/lh5351Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041468/lh5351Isup3.cml

checkCIF report

Comment top

N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin & Marinkovic, 2006; Mijin et al., 2008). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008, 2010). Crystal structures of some acetamide derivatives, viz., 2-(4-bromophenyl)-N-(2-methoxyphenyl)acetamide (Xiao et al., 2010), N-benzyl-2-(2-bromophenyl)-2-(2-nitrophenoxy) acetamide (Li & Wu, 2010) and N-(3-chloro-4-fluorophenyl)-2- (naphthalen-1-yl)acetamide (Praveen et al., 2011)have been reported. In view of the importance of amides, we report herein the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2010, 2011; Wang et al., 2010). The naphthalene ring system (C9-C18, maximum deviation of 0.038 (4) Å at atom C9) and the benzene ring (C1-C6) form dihedral angles of 69.5 (2) and 37.2 (2)°, respectively, with the acetamide moiety (O1/N1/C7/C8, maximum deviation of 0.004 (4) Å at atom C7). The naphthalene ring system forms a dihedral angle of 52.36 (18)° with the benzene ring.

In the crystal, (Fig. 2), molecules are linked via intermolecular N1–H1N1···O1ⁱ hydrogen bonds (Table 1) to form one-dimensional chains along [001].

Related literature top

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For the coordination abilities of amides, see: Wu et al. (2008, 2010). For related structures, see: Fun et al. (2010, 2011); Li & Wu (2010); Xiao et al. (2010); Praveen et al. (2011); Wang et al. (2010). For standard bond-length data, see: Allen et al. (1987).

Experimental top

Naphthalen-1-acetic acid (0.186g, 1 mmol) and 3,5-dichloroaniline (0.162g, 1 mmol) were dissolved in dichloromethane (20 ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, and was extracted thrice with dichloromethane. Organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Single crystals were grown from toluene and acetone mixture by the slow evaporation method (m.p.: 422-425 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N-(3,5-Dichlorophenyl)-2-(naphthalen-1-yl)acetamide top

Crystal data top

C₁₈H₁₃Cl₂NO	F(000) = 680
M_r = 330.19	D_x = 1.429 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3344 reflections
a = 7.8090 (14) Å	θ = 2.7–29.8°
b = 24.811 (4) Å	µ = 0.42 mm⁻¹
c = 9.6783 (13) Å	T = 296 K
β = 125.05 (1)°	Plate, colourless
V = 1535.1 (4) Å³	0.38 × 0.29 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4453 independent reflections
Radiation source: fine-focus sealed tube	2621 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→8
T_min = 0.855, T_max = 0.974	k = −33→34
16035 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0681P)² + 1.5936P] where P = (F_o² + 2F_c²)/3
4453 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₈H₁₃Cl₂NO	V = 1535.1 (4) Å³
M_r = 330.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8090 (14) Å	µ = 0.42 mm⁻¹
b = 24.811 (4) Å	T = 296 K
c = 9.6783 (13) Å	0.38 × 0.29 × 0.06 mm
β = 125.05 (1)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	4453 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2621 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.974	R_int = 0.051
16035 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.46 e Å⁻³
4453 reflections	Δρ_min = −0.33 e Å⁻³
203 parameters

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	0.6802 (2)	0.95869 (4)	0.44624 (14)	0.0775 (4)
Cl2	0.27251 (17)	0.91840 (5)	−0.21419 (12)	0.0771 (3)
O1	0.8282 (4)	0.75802 (9)	0.4568 (3)	0.0637 (7)
N1	0.8058 (4)	0.78590 (10)	0.2249 (3)	0.0414 (6)
C1	0.7351 (5)	0.86778 (12)	0.3249 (4)	0.0420 (6)
H1A	0.8298	0.8575	0.4369	0.050*
C2	0.6296 (5)	0.91611 (12)	0.2847 (4)	0.0485 (7)
C3	0.4862 (5)	0.93244 (13)	0.1200 (4)	0.0511 (8)
H3A	0.4155	0.9651	0.0954	0.061*
C4	0.4521 (5)	0.89863 (13)	−0.0058 (4)	0.0488 (7)
C5	0.5533 (5)	0.85030 (12)	0.0274 (4)	0.0440 (7)
H5A	0.5265	0.8282	−0.0606	0.053*
C6	0.6960 (4)	0.83471 (11)	0.1934 (3)	0.0377 (6)
C7	0.8686 (5)	0.75141 (12)	0.3535 (4)	0.0438 (7)
C8	0.9966 (6)	0.70397 (14)	0.3588 (5)	0.0580 (9)
H8A	0.9423	0.6935	0.2440	0.070*
H8B	1.1401	0.7156	0.4125	0.070*
C9	0.9946 (5)	0.65549 (13)	0.4519 (4)	0.0484 (7)
C10	0.8751 (6)	0.61214 (15)	0.3661 (6)	0.0665 (10)
H10A	0.7960	0.6125	0.2488	0.080*
C11	0.8659 (7)	0.56650 (17)	0.4478 (7)	0.0776 (13)
H11A	0.7824	0.5373	0.3852	0.093*
C12	0.9787 (8)	0.56556 (16)	0.6169 (8)	0.0826 (14)
H12A	0.9710	0.5356	0.6707	0.099*
C13	1.1104 (5)	0.60953 (14)	0.7160 (5)	0.0558 (9)
C14	1.2266 (8)	0.6089 (2)	0.8930 (7)	0.0880 (15)
H14A	1.2177	0.5794	0.9480	0.106*
C15	1.3489 (8)	0.6501 (3)	0.9818 (7)	0.0930 (16)
H15A	1.4222	0.6496	1.0987	0.112*
C16	1.3700 (6)	0.6941 (2)	0.9035 (6)	0.0808 (13)
H16A	1.4621	0.7217	0.9691	0.097*
C17	1.2573 (5)	0.69744 (16)	0.7315 (5)	0.0622 (9)
H17A	1.2705	0.7274	0.6807	0.075*
C18	1.1179 (5)	0.65423 (13)	0.6294 (4)	0.0464 (7)
H1N1	0.822 (5)	0.7771 (14)	0.154 (5)	0.055 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1246 (9)	0.0497 (5)	0.0709 (6)	0.0016 (5)	0.0636 (7)	−0.0107 (4)
Cl2	0.0783 (6)	0.0938 (8)	0.0501 (5)	0.0249 (5)	0.0315 (5)	0.0248 (5)
O1	0.1054 (19)	0.0600 (15)	0.0634 (15)	0.0303 (13)	0.0705 (15)	0.0228 (12)
N1	0.0576 (15)	0.0437 (14)	0.0380 (13)	0.0069 (11)	0.0363 (12)	0.0059 (10)
C1	0.0505 (16)	0.0400 (16)	0.0393 (14)	−0.0035 (12)	0.0280 (13)	0.0014 (12)
C2	0.0622 (19)	0.0408 (17)	0.0527 (18)	−0.0036 (14)	0.0388 (16)	−0.0025 (14)
C3	0.0610 (19)	0.0444 (18)	0.058 (2)	0.0096 (14)	0.0401 (17)	0.0085 (14)
C4	0.0522 (17)	0.0537 (19)	0.0464 (17)	0.0050 (14)	0.0318 (15)	0.0125 (14)
C5	0.0535 (17)	0.0475 (18)	0.0398 (15)	−0.0035 (13)	0.0319 (14)	0.0020 (12)
C6	0.0445 (15)	0.0372 (15)	0.0384 (14)	−0.0011 (11)	0.0279 (13)	0.0029 (11)
C7	0.0585 (17)	0.0451 (16)	0.0429 (15)	0.0079 (13)	0.0380 (15)	0.0071 (12)
C8	0.082 (2)	0.058 (2)	0.061 (2)	0.0252 (17)	0.057 (2)	0.0190 (16)
C9	0.0566 (18)	0.0458 (18)	0.0555 (19)	0.0134 (14)	0.0395 (16)	0.0054 (14)
C10	0.063 (2)	0.057 (2)	0.081 (3)	0.0047 (17)	0.042 (2)	−0.017 (2)
C11	0.083 (3)	0.050 (2)	0.119 (4)	−0.0045 (19)	0.069 (3)	−0.018 (2)
C12	0.106 (3)	0.047 (2)	0.141 (5)	0.020 (2)	0.098 (4)	0.020 (3)
C13	0.0616 (19)	0.054 (2)	0.069 (2)	0.0263 (16)	0.0474 (18)	0.0243 (17)
C14	0.101 (4)	0.105 (4)	0.084 (3)	0.050 (3)	0.068 (3)	0.045 (3)
C15	0.072 (3)	0.134 (5)	0.066 (3)	0.033 (3)	0.035 (2)	0.022 (3)
C16	0.047 (2)	0.114 (4)	0.064 (3)	−0.002 (2)	0.0219 (19)	−0.014 (3)
C17	0.0520 (19)	0.073 (2)	0.067 (2)	0.0016 (17)	0.0376 (18)	−0.0055 (19)
C18	0.0479 (16)	0.0506 (18)	0.0517 (17)	0.0164 (13)	0.0350 (15)	0.0117 (14)

Geometric parameters (Å, º) top

Cl1—C2	1.734 (3)	C9—C10	1.352 (5)
Cl2—C4	1.740 (3)	C9—C18	1.407 (4)
O1—C7	1.220 (3)	C10—C11	1.406 (6)
N1—C7	1.349 (4)	C10—H10A	0.9300
N1—C6	1.412 (4)	C11—C12	1.341 (7)
N1—H1N1	0.80 (4)	C11—H11A	0.9300
C1—C2	1.378 (4)	C12—C13	1.426 (6)
C1—C6	1.393 (4)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.405 (6)
C2—C3	1.381 (5)	C13—C18	1.411 (4)
C3—C4	1.373 (5)	C14—C15	1.325 (7)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.369 (4)	C15—C16	1.392 (7)
C5—C6	1.385 (4)	C15—H15A	0.9300
C5—H5A	0.9300	C16—C17	1.367 (6)
C7—C8	1.526 (4)	C16—H16A	0.9300
C8—C9	1.509 (5)	C17—C18	1.441 (5)
C8—H8A	0.9700	C17—H17A	0.9300
C8—H8B	0.9700

C7—N1—C6	126.6 (2)	C10—C9—C18	118.6 (3)
C7—N1—H1N1	118 (3)	C10—C9—C8	120.5 (3)
C6—N1—H1N1	115 (3)	C18—C9—C8	120.8 (3)
C2—C1—C6	118.2 (3)	C9—C10—C11	122.4 (4)
C2—C1—H1A	120.9	C9—C10—H10A	118.8
C6—C1—H1A	120.9	C11—C10—H10A	118.8
C1—C2—C3	122.6 (3)	C12—C11—C10	119.4 (4)
C1—C2—Cl1	119.1 (2)	C12—C11—H11A	120.3
C3—C2—Cl1	118.4 (2)	C10—C11—H11A	120.3
C4—C3—C2	117.4 (3)	C11—C12—C13	121.4 (4)
C4—C3—H3A	121.3	C11—C12—H12A	119.3
C2—C3—H3A	121.3	C13—C12—H12A	119.3
C5—C4—C3	122.4 (3)	C14—C13—C18	121.0 (4)
C5—C4—Cl2	119.4 (3)	C14—C13—C12	121.5 (4)
C3—C4—Cl2	118.2 (3)	C18—C13—C12	117.5 (4)
C4—C5—C6	119.2 (3)	C15—C14—C13	120.2 (5)
C4—C5—H5A	120.4	C15—C14—H14A	119.9
C6—C5—H5A	120.4	C13—C14—H14A	119.9
C5—C6—C1	120.3 (3)	C14—C15—C16	121.3 (5)
C5—C6—N1	118.3 (3)	C14—C15—H15A	119.4
C1—C6—N1	121.4 (3)	C16—C15—H15A	119.4
O1—C7—N1	122.9 (3)	C17—C16—C15	121.0 (5)
O1—C7—C8	123.3 (3)	C17—C16—H16A	119.5
N1—C7—C8	113.8 (2)	C15—C16—H16A	119.5
C9—C8—C7	113.8 (3)	C16—C17—C18	119.7 (4)
C9—C8—H8A	108.8	C16—C17—H17A	120.2
C7—C8—H8A	108.8	C18—C17—H17A	120.2
C9—C8—H8B	108.8	C9—C18—C13	120.6 (3)
C7—C8—H8B	108.8	C9—C18—C17	122.6 (3)
H8A—C8—H8B	107.7	C13—C18—C17	116.8 (3)

C6—C1—C2—C3	0.7 (5)	C8—C9—C10—C11	−178.9 (3)
C6—C1—C2—Cl1	−178.5 (2)	C9—C10—C11—C12	0.2 (6)
C1—C2—C3—C4	−0.6 (5)	C10—C11—C12—C13	−0.9 (6)
Cl1—C2—C3—C4	178.6 (2)	C11—C12—C13—C14	179.2 (4)
C2—C3—C4—C5	0.4 (5)	C11—C12—C13—C18	−0.1 (5)
C2—C3—C4—Cl2	−179.9 (2)	C18—C13—C14—C15	−1.3 (6)
C3—C4—C5—C6	−0.2 (5)	C12—C13—C14—C15	179.4 (4)
Cl2—C4—C5—C6	−180.0 (2)	C13—C14—C15—C16	−1.7 (7)
C4—C5—C6—C1	0.3 (4)	C14—C15—C16—C17	3.1 (7)
C4—C5—C6—N1	−177.1 (3)	C15—C16—C17—C18	−1.4 (6)
C2—C1—C6—C5	−0.5 (4)	C10—C9—C18—C13	−2.6 (4)
C2—C1—C6—N1	176.8 (3)	C8—C9—C18—C13	177.9 (3)
C7—N1—C6—C5	−146.4 (3)	C10—C9—C18—C17	177.1 (3)
C7—N1—C6—C1	36.2 (4)	C8—C9—C18—C17	−2.4 (4)
C6—N1—C7—O1	3.1 (5)	C14—C13—C18—C9	−177.4 (3)
C6—N1—C7—C8	−176.2 (3)	C12—C13—C18—C9	1.9 (4)
O1—C7—C8—C9	23.7 (5)	C14—C13—C18—C17	2.9 (5)
N1—C7—C8—C9	−157.1 (3)	C12—C13—C18—C17	−177.9 (3)
C7—C8—C9—C10	103.2 (4)	C16—C17—C18—C9	178.8 (3)
C7—C8—C9—C18	−77.3 (4)	C16—C17—C18—C13	−1.5 (5)
C18—C9—C10—C11	1.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.80 (4)	2.12 (4)	2.911 (4)	170 (4)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Cl₂NO
M_r	330.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.8090 (14), 24.811 (4), 9.6783 (13)
β (°)	125.05 (1)
V (Å³)	1535.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.38 × 0.29 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.855, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	16035, 4453, 2621
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.198, 1.03
No. of reflections	4453
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)	0.46, −0.33

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
N1—H1N1···O1ⁱ	0.80 (4)	2.12 (4)	2.911 (4)	170 (4)

Symmetry code: (i) x, −y+3/2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC-New Delhi, Government of India, for financial assistance for the purchase of chemicals through a BSR one-time grant.

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