N-(3-Chloro-4-fluoro­phen­yl)-2-(naphthalen-1-yl)acetamide

Praveen, A.S.; Jasinski, J.P.; Golen, J.A.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811024597

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1826

doi:10.1107/S1600536811024597

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N-(3-Chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide

A. S. Praveen,^a Jerry P. Jasinski,^b ^* James A. Golen,^b B. Narayana ^c and H. S. Yathirajan ^a

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 21 June 2011; accepted 22 June 2011; online 25 June 2011)

In the title compound, C₁₈H₁₃ClFNO, the dihedral angle between the mean planes of the chloro- and fluoro-substituted benzene ring and the naphthalene ring system is 60.5 (8)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming a zigzag chain along [101].

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: Davis & Healy (2010 ); Li et al. (2010 ); Li & Wu (2010 ); Wang et al. (2010 ); Xiao et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₃ClFNO
M_r = 313.74
Monoclinic, P 2₁ /n
a = 8.096 (6) Å
b = 23.323 (6) Å
c = 8.404 (3) Å
β = 110.83 (5)°
V = 1483.4 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 173 K
0.30 × 0.18 × 0.10 mm

Data collection

Oxford Diffraction Oxford Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.924, T_max = 0.974
13979 measured reflections
3679 independent reflections
2947 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.04
3679 reflections
202 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.85 (1)	2.12 (2)	2.914 (2)	157 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024597/is2737sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024597/is2737Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024597/is2737Isup3.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 et al., 2006, 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-(3-chloro-4-hydroxyphenyl)acetamide (Davis & Healy, 2010), 2-(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yloxy)-N-(o-tolyl)acetamide (Li et al., 2010), N-benzyl-2-(2-bromophenyl)-2-(2-nitrophenoxy) acetamide (Li & Wu, 2010) and N-(4-chlorophenyl)-2-(8-quinolyloxy)acetamide monohydrate (Wang et al., 2010) have been reported. In view of the importance of amides, we report herein the crystal structure of the title compound, (I), C₁₈H₁₃ClFNO.

In the title compound, C₁₈H₁₃ClFNO, the dihedral angle between the mean planes of the chloro, fluoro substituted benzene ring and the naphthalene-1-yl ring is 60.5 (8)° (Fig. 2). Bond distances are in normal ranges (Allen et al., 1987). Crystal packing is stabilized by N—H···O hydrogen bonds (Fig. 3 and Table 1).

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: Davis & Healy (2010); Li et al. (2010); Li & Wu (2010); Wang et al. (2010); Xiao et al. (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Naphthalen-1-ylacetyl chloride (0.204 g, 1 mmol) and 3-chloro-4-fluoroaniline (0.145 g, 1 mmol) were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h (Fig. 1). The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which 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 (I). Single crystals were grown from toluene by the slow evaporation method (M.P.: 421 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Reaction scheme of the title compound, (I).
	Fig. 2. Molecular structure of the title compound, showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 3. Packing diagram of the title compound viewed down the c axis. Dashed lines represent N—H···O hydrogen bonds.

N-(3-Chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide top

Crystal data top

C₁₈H₁₃ClFNO	F(000) = 648
M_r = 313.74	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4655 reflections
a = 8.096 (6) Å	θ = 3.1–32.5°
b = 23.323 (6) Å	µ = 0.27 mm⁻¹
c = 8.404 (3) Å	T = 173 K
β = 110.83 (5)°	Block, colorless
V = 1483.4 (13) Å³	0.30 × 0.18 × 0.10 mm
Z = 4

Data collection top

Oxford Diffraction Oxford Xcalibur Eos Gemini diffractometer	3679 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2947 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 16.1500 pixels mm^-1	θ_max = 28.3°, θ_min = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −31→31
T_min = 0.924, T_max = 0.974	l = −10→11
13979 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0495P)² + 0.4725P] where P = (F_o² + 2F_c²)/3
3679 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₈H₁₃ClFNO	V = 1483.4 (13) Å³
M_r = 313.74	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.096 (6) Å	µ = 0.27 mm⁻¹
b = 23.323 (6) Å	T = 173 K
c = 8.404 (3) Å	0.30 × 0.18 × 0.10 mm
β = 110.83 (5)°

Data collection top

Oxford Diffraction Oxford Xcalibur Eos Gemini diffractometer	3679 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2947 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.974	R_int = 0.024
13979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.25 e Å⁻³
3679 reflections	Δρ_min = −0.31 e Å⁻³
202 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 > 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
Cl1	0.38936 (7)	0.11723 (2)	1.00561 (6)	0.06507 (18)
F1	0.17103 (16)	0.03432 (5)	0.75440 (15)	0.0629 (3)
O1	0.21705 (14)	0.22471 (5)	0.22432 (14)	0.0486 (3)
N1	0.43807 (16)	0.20845 (6)	0.47811 (16)	0.0379 (3)
H1N	0.538 (2)	0.2204 (7)	0.544 (2)	0.046*
C1	0.4025 (2)	0.16306 (7)	0.71760 (19)	0.0380 (3)
H1B	0.4762	0.1917	0.7880	0.046*
C2	0.3379 (2)	0.11924 (7)	0.7882 (2)	0.0414 (4)
C3	0.2317 (2)	0.07766 (7)	0.6847 (2)	0.0428 (4)
C4	0.1869 (2)	0.07943 (7)	0.5115 (2)	0.0426 (4)
H4A	0.1126	0.0507	0.4417	0.051*
C5	0.2506 (2)	0.12309 (6)	0.43962 (19)	0.0385 (3)
H5A	0.2205	0.1247	0.3197	0.046*
C6	0.35908 (18)	0.16496 (6)	0.54278 (18)	0.0346 (3)
C7	0.36895 (18)	0.23348 (6)	0.32430 (18)	0.0347 (3)
C8	0.4966 (2)	0.27172 (7)	0.2798 (2)	0.0407 (3)
H8A	0.5850	0.2870	0.3858	0.049*
H8B	0.5604	0.2488	0.2209	0.049*
C9	0.40433 (19)	0.32093 (6)	0.16728 (19)	0.0373 (3)
C10	0.3683 (2)	0.31871 (8)	−0.0039 (2)	0.0460 (4)
H10A	0.4071	0.2866	−0.0507	0.055*
C11	0.2745 (2)	0.36315 (9)	−0.1131 (2)	0.0555 (5)
H11A	0.2509	0.3606	−0.2320	0.067*
C12	0.2185 (2)	0.40899 (8)	−0.0499 (2)	0.0545 (5)
H12A	0.1538	0.4383	−0.1248	0.065*
C13	0.2547 (2)	0.41419 (7)	0.1263 (2)	0.0449 (4)
C14	0.2016 (3)	0.46210 (8)	0.1974 (3)	0.0609 (5)
H14A	0.1363	0.4918	0.1247	0.073*
C15	0.2418 (3)	0.46677 (9)	0.3675 (3)	0.0695 (6)
H15A	0.2056	0.4997	0.4130	0.083*
C16	0.3361 (3)	0.42340 (9)	0.4765 (3)	0.0633 (5)
H16A	0.3648	0.4274	0.5958	0.076*
C17	0.3873 (2)	0.37576 (7)	0.4146 (2)	0.0482 (4)
H17A	0.4493	0.3463	0.4906	0.058*
C18	0.34938 (19)	0.36936 (7)	0.2373 (2)	0.0384 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0760 (4)	0.0795 (4)	0.0392 (2)	−0.0043 (3)	0.0199 (2)	0.0062 (2)
F1	0.0707 (7)	0.0521 (6)	0.0693 (7)	−0.0078 (5)	0.0291 (6)	0.0142 (5)
O1	0.0360 (6)	0.0473 (6)	0.0456 (6)	−0.0067 (5)	−0.0064 (5)	0.0111 (5)
N1	0.0282 (6)	0.0420 (7)	0.0344 (6)	−0.0039 (5)	−0.0002 (5)	0.0035 (5)
C1	0.0342 (7)	0.0390 (8)	0.0366 (7)	0.0023 (6)	0.0072 (6)	−0.0021 (6)
C2	0.0395 (8)	0.0478 (9)	0.0359 (7)	0.0078 (7)	0.0120 (6)	0.0047 (6)
C3	0.0392 (8)	0.0380 (8)	0.0522 (9)	0.0042 (6)	0.0175 (7)	0.0077 (7)
C4	0.0385 (8)	0.0351 (7)	0.0492 (9)	−0.0008 (6)	0.0096 (7)	−0.0033 (6)
C5	0.0363 (8)	0.0395 (8)	0.0353 (7)	0.0004 (6)	0.0072 (6)	−0.0018 (6)
C6	0.0273 (6)	0.0363 (7)	0.0358 (7)	0.0044 (5)	0.0060 (6)	0.0029 (6)
C7	0.0307 (7)	0.0316 (7)	0.0352 (7)	0.0031 (5)	0.0037 (6)	0.0001 (5)
C8	0.0315 (7)	0.0425 (8)	0.0433 (8)	0.0013 (6)	0.0073 (6)	0.0056 (6)
C9	0.0296 (7)	0.0401 (8)	0.0374 (7)	−0.0049 (6)	0.0058 (6)	0.0060 (6)
C10	0.0420 (9)	0.0526 (10)	0.0402 (8)	−0.0100 (7)	0.0107 (7)	−0.0010 (7)
C11	0.0505 (10)	0.0740 (13)	0.0348 (8)	−0.0145 (9)	0.0064 (7)	0.0117 (8)
C12	0.0429 (9)	0.0570 (11)	0.0527 (10)	−0.0052 (8)	0.0037 (8)	0.0241 (8)
C13	0.0333 (8)	0.0420 (8)	0.0544 (9)	−0.0035 (6)	0.0094 (7)	0.0135 (7)
C14	0.0519 (11)	0.0419 (9)	0.0868 (15)	0.0050 (8)	0.0222 (10)	0.0154 (9)
C15	0.0762 (14)	0.0506 (11)	0.0893 (16)	0.0019 (10)	0.0386 (13)	−0.0080 (11)
C16	0.0754 (14)	0.0589 (12)	0.0604 (12)	−0.0043 (10)	0.0302 (11)	−0.0072 (9)
C17	0.0509 (10)	0.0481 (9)	0.0428 (9)	−0.0026 (7)	0.0133 (8)	0.0034 (7)
C18	0.0309 (7)	0.0390 (8)	0.0414 (8)	−0.0050 (6)	0.0081 (6)	0.0063 (6)

Geometric parameters (Å, º) top

Cl1—C2	1.7242 (17)	C9—C10	1.363 (2)
F1—C3	1.3454 (19)	C9—C18	1.416 (2)
O1—C7	1.235 (2)	C10—C11	1.414 (3)
N1—C7	1.3457 (19)	C10—H10A	0.9500
N1—C6	1.407 (2)	C11—C12	1.343 (3)
N1—H1N	0.849 (14)	C11—H11A	0.9500
C1—C2	1.375 (2)	C12—C13	1.409 (3)
C1—C6	1.385 (2)	C12—H12A	0.9500
C1—H1B	0.9500	C13—C14	1.405 (3)
C2—C3	1.380 (2)	C13—C18	1.429 (2)
C3—C4	1.370 (2)	C14—C15	1.353 (3)
C4—C5	1.375 (2)	C14—H14A	0.9500
C4—H4A	0.9500	C15—C16	1.396 (3)
C5—C6	1.391 (2)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.353 (3)
C7—C8	1.510 (2)	C16—H16A	0.9500
C8—C9	1.506 (2)	C17—C18	1.418 (2)
C8—H8A	0.9900	C17—H17A	0.9500
C8—H8B	0.9900

C7—N1—C6	126.36 (13)	C10—C9—C18	119.18 (14)
C7—N1—H1N	117.4 (12)	C10—C9—C8	120.38 (15)
C6—N1—H1N	116.2 (12)	C18—C9—C8	120.41 (14)
C2—C1—C6	119.32 (14)	C9—C10—C11	121.43 (18)
C2—C1—H1B	120.3	C9—C10—H10A	119.3
C6—C1—H1B	120.3	C11—C10—H10A	119.3
C1—C2—C3	119.85 (15)	C12—C11—C10	120.37 (17)
C1—C2—Cl1	119.47 (13)	C12—C11—H11A	119.8
C3—C2—Cl1	120.68 (13)	C10—C11—H11A	119.8
F1—C3—C4	119.05 (15)	C11—C12—C13	120.77 (16)
F1—C3—C2	119.71 (15)	C11—C12—H12A	119.6
C4—C3—C2	121.24 (15)	C13—C12—H12A	119.6
C3—C4—C5	119.37 (15)	C14—C13—C12	122.34 (17)
C3—C4—H4A	120.3	C14—C13—C18	118.60 (17)
C5—C4—H4A	120.3	C12—C13—C18	119.06 (17)
C4—C5—C6	119.90 (14)	C15—C14—C13	121.24 (18)
C4—C5—H5A	120.0	C15—C14—H14A	119.4
C6—C5—H5A	120.0	C13—C14—H14A	119.4
C1—C6—C5	120.32 (14)	C14—C15—C16	120.3 (2)
C1—C6—N1	117.00 (13)	C14—C15—H15A	119.8
C5—C6—N1	122.56 (14)	C16—C15—H15A	119.8
O1—C7—N1	123.71 (15)	C17—C16—C15	120.9 (2)
O1—C7—C8	122.22 (14)	C17—C16—H16A	119.5
N1—C7—C8	114.01 (13)	C15—C16—H16A	119.5
C9—C8—C7	112.03 (13)	C16—C17—C18	120.59 (17)
C9—C8—H8A	109.2	C16—C17—H17A	119.7
C7—C8—H8A	109.2	C18—C17—H17A	119.7
C9—C8—H8B	109.2	C9—C18—C17	122.51 (14)
C7—C8—H8B	109.2	C9—C18—C13	119.17 (15)
H8A—C8—H8B	107.9	C17—C18—C13	118.31 (16)

C6—C1—C2—C3	0.3 (2)	C18—C9—C10—C11	−1.2 (2)
C6—C1—C2—Cl1	−179.17 (11)	C8—C9—C10—C11	176.99 (15)
C1—C2—C3—F1	178.93 (14)	C9—C10—C11—C12	0.1 (3)
Cl1—C2—C3—F1	−1.6 (2)	C10—C11—C12—C13	1.1 (3)
C1—C2—C3—C4	−0.8 (2)	C11—C12—C13—C14	178.56 (17)
Cl1—C2—C3—C4	178.65 (13)	C11—C12—C13—C18	−1.1 (2)
F1—C3—C4—C5	−179.02 (14)	C12—C13—C14—C15	−178.31 (18)
C2—C3—C4—C5	0.7 (2)	C18—C13—C14—C15	1.4 (3)
C3—C4—C5—C6	−0.1 (2)	C13—C14—C15—C16	−0.6 (3)
C2—C1—C6—C5	0.3 (2)	C14—C15—C16—C17	−0.8 (3)
C2—C1—C6—N1	−175.86 (14)	C15—C16—C17—C18	1.3 (3)
C4—C5—C6—C1	−0.4 (2)	C10—C9—C18—C17	−177.71 (15)
C4—C5—C6—N1	175.56 (14)	C8—C9—C18—C17	4.1 (2)
C7—N1—C6—C1	−150.76 (15)	C10—C9—C18—C13	1.2 (2)
C7—N1—C6—C5	33.2 (2)	C8—C9—C18—C13	−177.05 (13)
C6—N1—C7—O1	6.9 (3)	C16—C17—C18—C9	178.35 (17)
C6—N1—C7—C8	−170.51 (14)	C16—C17—C18—C13	−0.5 (2)
O1—C7—C8—C9	33.6 (2)	C14—C13—C18—C9	−179.71 (15)
N1—C7—C8—C9	−148.94 (14)	C12—C13—C18—C9	0.0 (2)
C7—C8—C9—C10	−100.15 (18)	C14—C13—C18—C17	−0.8 (2)
C7—C8—C9—C18	78.05 (18)	C12—C13—C18—C17	178.91 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.85 (1)	2.12 (2)	2.914 (2)	157 (2)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃ClFNO
M_r	313.74
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	8.096 (6), 23.323 (6), 8.404 (3)
β (°)	110.83 (5)
V (Å³)	1483.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.18 × 0.10

Data collection
Diffractometer	Oxford Diffraction Oxford Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.924, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	13979, 3679, 2947
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.04
No. of reflections	3679
No. of parameters	202
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.31

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.849 (14)	2.115 (15)	2.914 (2)	156.6 (17)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

ASP thanks the UOM for research facilities. BN thanks Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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