(1E,4E)-1-(3-Nitro­phen­yl)-5-phenyl­penta-1,4-dien-3-one

Samshuddin, S.; Butcher, R.J.; Akkurt, M.; Narayana, B.; Sarojini, B.K.; Yathirajan, H.S.

doi:10.1107/S1600536811052548

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o74-o75

doi:10.1107/S1600536811052548

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(1E,4E)-1-(3-Nitrophenyl)-5-phenylpenta-1,4-dien-3-one

S. Samshuddin,^a Ray J. Butcher,^b Mehmet Akkurt,^c ^* B. Narayana,^a B. K. Sarojini ^d and H. S. Yathirajan ^e

^aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Chemistry, P. A. College of Engineering, Nadupadav, Mangalore-574 153, India, and ^eDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 5 December 2011; accepted 6 December 2011; online 10 December 2011)

In the title compound, C₁₇H₁₃NO₃, the dihedral angle between the benzene rings is 31.21 (5)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds occur. A C—H⋯π interaction is also indicated.

Related literature

For the pharmacological importance of chalcones and bis chalcones, see: Sarojini et al. (2006 ); Dhar (1981 ); Dimmock et al. (1999 ); Satyanarayana et al. (2004 ). For our work on synthesis of different derivatives of chalcones, see: Baktır et al. (2011 ); Fun et al. (2010 ); Jasinski et al. (2010 ); Samshuddin et al. (2011a ,b ,c ). For related structures, see: Butcher et al. (2006a ,b ; 2007a ,b ,c ); Harrison et al. (2006 ); Hu et al. (2004 ); Fischer et al. (2007 ); Patil et al. (2007 ); Zhao et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₃NO₃
M_r = 279.28
Monoclinic, P 2₁ /c
a = 11.9806 (6) Å
b = 9.8955 (4) Å
c = 12.5562 (7) Å
β = 114.992 (7)°
V = 1349.21 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.44 × 0.34 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.969, T_max = 1.000
7835 measured reflections
3746 independent reflections
2453 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.128
S = 1.02
3746 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3ⁱ	0.93	2.59	3.412 (2)	147
C5—H5A⋯Cg1ⁱⁱ	0.93	2.62	3.3915 (19)	141
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ), PARST (Nardelli, 1983 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811052548/tk5031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052548/tk5031Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052548/tk5031Isup3.cml

checkCIF report

Comment top

Chalcones are highly reactive substances of varied nature. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006). The basic skeleton of chalcones which possess α,β-unsaturated carbonyl group is useful for the synthesis of various biodynamic cyclic derivatives such as pyrazoline, benzodiazepine, 2,4,6-triaryl pyridine, isoxazoline and cyclohexenone derivatives (Samshuddin et al., 2011a,b,c; Fun et al., 2010; Jasinski et al., 2010; Baktır et al., 2011).

The crystal structures of some bis-chalcones viz., 2,6-bis(4-methoxybenzylidene)cyclohexanone (Butcher et al., 2006a), 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al., 2006b), 1,5-bis(3,4-dimethoxyphenyl)penta-1,4-dien-3-one (Butcher et al., 2007a), 1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one (Butcher et al., 2007b), 2,5-bis(3,4-dimethoxybenzylidene)cyclopentanone (Butcher et al., 2007c), 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one (Harrison et al., 2006), 2,4-dimethyl-1,5-diphenylpenta-1,4-dien-3-one (Hu et al., 2004) have been reported. In continuation of our work on synthesis of chalcone derivatives, the title compound (I) was prepared and its crystal structure is reported.

In the title molecule (I), (Fig. 1), bond lengths and angles are comparable to closely related structures (Patil et al., 2007; Zhao et al., 2007; Fischer et al., 2007; Butcher et al. (2006a,b, 2007a,b,c); Harrison et al. (2006); Hu et al. (2004). The least-squares plane through the C7–C11/O3 group makes dihedral angles of 8.22 (6) and 32.14 (6)° with the C1–C6 benzene ring and the C12–C17 phenyl ring, respectively. The dihedral angle between these rings is 31.21 (5)° and the nitro group at C3 lies close to the C1–C6 ring plane, with O1–N1–C3–C2 and O2–N1–C3–C4 torsion angles of 6.3 (3) and 7.4 (3)°, respectively.

The molecular packing of (I) shown in Fig. 2 is stabilized by C—H···O interactions (Table 1), which lead to the formation of a centrosymmetric dimer, and is further consolidated by C—H···π interactions (Table 1) involving the C12–C17 phenyl ring.

Related literature top

For the pharmacological importance of chalcones and bis chalcones, see: Sarojini et al. (2006); Dhar (1981); Dimmock et al. (1999); Satyanarayana et al. (2004). For our work on synthesis of different derivatives of chalcones, see: Baktır et al. (2011); Fun et al. (2010); Jasinski et al. (2010); Samshuddin et al. (2011a,b,c). For related structures, see: Butcher et al. (2006a,b; 2007a,b,c); Harrison et al. (2006); Hu et al. (2004); Fischer et al. (2007); Patil et al. (2007); Zhao et al. (2007).

Experimental top

Synthesis of title compound was carried out by stirring a mixture of benzylidene acetone (1.46 g, 0.01 mol) and 3-nitrobenzaldehyde (1.51 g, 0.01 mol) in 40 ml of ethanolic sodium hydroxide at 278–283 K for 3 h. The precipitate was collected by filtration and purified by recrystallization from ethanol. The single crystal was grown from 1,4-dioxane by the slow evaporation method and yield of the compound was 80%. (M.pt. 414 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1983) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

(1E,4E)-1-(3-Nitrophenyl)-5-phenylpenta-1,4-dien-3-one top

Crystal data top

C₁₇H₁₃NO₃	F(000) = 584
M_r = 279.28	D_x = 1.375 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2209 reflections
a = 11.9806 (6) Å	θ = 3.1–30.9°
b = 9.8955 (4) Å	µ = 0.10 mm⁻¹
c = 12.5562 (7) Å	T = 293 K
β = 114.992 (7)°	Plate, colourless
V = 1349.21 (14) Å³	0.44 × 0.34 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3746 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 10.5081 pixels mm^-1	θ_max = 30.9°, θ_min = 3.3°
ω scans	h = −17→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −13→14
T_min = 0.969, T_max = 1.000	l = −11→18
7835 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.047P)² + 0.2703P] where P = (F_o² + 2F_c²)/3
3746 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₁₃NO₃	V = 1349.21 (14) Å³
M_r = 279.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9806 (6) Å	µ = 0.10 mm⁻¹
b = 9.8955 (4) Å	T = 293 K
c = 12.5562 (7) Å	0.44 × 0.34 × 0.08 mm
β = 114.992 (7)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3746 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2453 reflections with I > 2σ(I)
T_min = 0.969, T_max = 1.000	R_int = 0.033
7835 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
3746 reflections	Δρ_min = −0.26 e Å⁻³
190 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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	0.17385 (11)	0.14120 (12)	0.04941 (10)	0.0346 (4)
O2	0.11627 (15)	0.33639 (14)	−0.03094 (11)	0.0526 (5)
O3	0.54296 (11)	0.04578 (11)	0.67363 (10)	0.0288 (4)
N1	0.16833 (13)	0.26465 (15)	0.05501 (12)	0.0291 (4)
C1	0.34756 (14)	0.30928 (16)	0.37830 (13)	0.0208 (4)
C2	0.29603 (14)	0.25023 (16)	0.26714 (13)	0.0211 (4)
C3	0.22682 (14)	0.32911 (16)	0.17068 (13)	0.0226 (5)
C4	0.20852 (15)	0.46592 (17)	0.17935 (14)	0.0248 (5)
C5	0.26174 (15)	0.52505 (17)	0.28955 (14)	0.0247 (5)
C6	0.32965 (15)	0.44777 (16)	0.38746 (14)	0.0242 (5)
C7	0.41680 (14)	0.22370 (16)	0.48051 (14)	0.0225 (5)
C8	0.46170 (14)	0.26055 (16)	0.59296 (14)	0.0227 (5)
C9	0.53494 (14)	0.16722 (16)	0.68958 (14)	0.0225 (5)
C10	0.60212 (14)	0.23207 (16)	0.80546 (13)	0.0221 (5)
C11	0.70265 (14)	0.17661 (16)	0.88844 (13)	0.0226 (5)
C12	0.78098 (14)	0.23472 (16)	1.00356 (13)	0.0211 (4)
C13	0.74719 (15)	0.34930 (17)	1.04775 (14)	0.0256 (5)
C14	0.82268 (16)	0.39866 (17)	1.15834 (15)	0.0296 (5)
C15	0.93264 (16)	0.33433 (18)	1.22672 (15)	0.0307 (5)
C16	0.96719 (15)	0.22128 (18)	1.18395 (15)	0.0288 (5)
C17	0.89256 (15)	0.17173 (17)	1.07295 (14)	0.0258 (5)
H2A	0.30800	0.15890	0.25790	0.0250*
H4A	0.16180	0.51670	0.11310	0.0300*
H5A	0.25180	0.61710	0.29780	0.0300*
H6A	0.36420	0.48870	0.46100	0.0290*
H7A	0.43070	0.13480	0.46530	0.0270*
H8A	0.44660	0.34770	0.61140	0.0270*
H10A	0.57350	0.31380	0.82090	0.0260*
H11A	0.72550	0.09230	0.87160	0.0270*
H13A	0.67340	0.39290	1.00270	0.0310*
H14A	0.79940	0.47530	1.18680	0.0360*
H15A	0.98280	0.36730	1.30110	0.0370*
H16A	1.04090	0.17790	1.22970	0.0350*
H17A	0.91710	0.09590	1.04460	0.0310*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0408 (8)	0.0265 (6)	0.0284 (7)	−0.0001 (6)	0.0068 (6)	−0.0062 (6)
O2	0.0800 (11)	0.0377 (8)	0.0184 (7)	−0.0015 (8)	−0.0003 (7)	0.0065 (6)
O3	0.0347 (7)	0.0216 (6)	0.0241 (6)	0.0027 (5)	0.0066 (5)	−0.0001 (5)
N1	0.0322 (8)	0.0298 (8)	0.0206 (7)	−0.0031 (7)	0.0066 (6)	−0.0004 (7)
C1	0.0195 (7)	0.0224 (8)	0.0202 (8)	0.0009 (6)	0.0082 (7)	0.0004 (7)
C2	0.0216 (7)	0.0183 (7)	0.0243 (8)	0.0010 (6)	0.0107 (7)	0.0001 (7)
C3	0.0240 (8)	0.0249 (8)	0.0171 (8)	−0.0039 (7)	0.0070 (7)	−0.0009 (7)
C4	0.0270 (8)	0.0251 (8)	0.0211 (8)	0.0029 (7)	0.0091 (7)	0.0067 (7)
C5	0.0307 (9)	0.0199 (8)	0.0270 (9)	0.0024 (7)	0.0156 (7)	0.0023 (7)
C6	0.0278 (8)	0.0259 (8)	0.0199 (8)	−0.0011 (7)	0.0112 (7)	−0.0032 (7)
C7	0.0216 (8)	0.0207 (8)	0.0226 (8)	0.0013 (7)	0.0068 (7)	−0.0001 (7)
C8	0.0228 (8)	0.0211 (8)	0.0230 (8)	0.0016 (7)	0.0085 (7)	−0.0001 (7)
C9	0.0204 (8)	0.0240 (8)	0.0222 (8)	−0.0003 (7)	0.0081 (7)	0.0012 (7)
C10	0.0253 (8)	0.0207 (8)	0.0192 (8)	0.0012 (7)	0.0084 (7)	0.0014 (7)
C11	0.0268 (8)	0.0206 (8)	0.0215 (8)	−0.0006 (7)	0.0112 (7)	0.0010 (7)
C12	0.0223 (8)	0.0227 (8)	0.0177 (7)	−0.0028 (7)	0.0079 (7)	0.0029 (7)
C13	0.0239 (8)	0.0259 (8)	0.0238 (8)	−0.0001 (7)	0.0071 (7)	0.0027 (7)
C14	0.0334 (9)	0.0262 (9)	0.0274 (9)	−0.0039 (8)	0.0111 (8)	−0.0043 (8)
C15	0.0310 (9)	0.0338 (10)	0.0223 (9)	−0.0092 (8)	0.0064 (8)	−0.0038 (8)
C16	0.0209 (8)	0.0352 (10)	0.0253 (9)	−0.0005 (7)	0.0050 (7)	0.0049 (8)
C17	0.0251 (8)	0.0264 (8)	0.0255 (8)	0.0006 (7)	0.0104 (7)	0.0010 (7)

Geometric parameters (Å, º) top

O1—N1	1.2270 (19)	C13—C14	1.387 (2)
O2—N1	1.2202 (19)	C14—C15	1.386 (3)
O3—C9	1.2287 (19)	C15—C16	1.378 (3)
N1—C3	1.465 (2)	C16—C17	1.389 (2)
C1—C2	1.394 (2)	C2—H2A	0.9300
C1—C6	1.399 (2)	C4—H4A	0.9300
C1—C7	1.467 (2)	C5—H5A	0.9300
C2—C3	1.384 (2)	C6—H6A	0.9300
C3—C4	1.383 (2)	C7—H7A	0.9300
C4—C5	1.385 (2)	C8—H8A	0.9300
C5—C6	1.383 (2)	C10—H10A	0.9300
C7—C8	1.332 (2)	C11—H11A	0.9300
C8—C9	1.482 (2)	C13—H13A	0.9300
C9—C10	1.479 (2)	C14—H14A	0.9300
C10—C11	1.333 (2)	C15—H15A	0.9300
C11—C12	1.468 (2)	C16—H16A	0.9300
C12—C13	1.395 (2)	C17—H17A	0.9300
C12—C17	1.397 (2)

O1—N1—O2	123.25 (14)	C12—C17—C16	120.61 (16)
O1—N1—C3	118.38 (13)	C1—C2—H2A	120.00
O2—N1—C3	118.36 (14)	C3—C2—H2A	120.00
C2—C1—C6	118.32 (14)	C3—C4—H4A	121.00
C2—C1—C7	118.78 (14)	C5—C4—H4A	121.00
C6—C1—C7	122.89 (14)	C4—C5—H5A	120.00
C1—C2—C3	119.22 (15)	C6—C5—H5A	120.00
N1—C3—C2	118.73 (14)	C1—C6—H6A	119.00
N1—C3—C4	118.61 (14)	C5—C6—H6A	119.00
C2—C3—C4	122.65 (14)	C1—C7—H7A	117.00
C3—C4—C5	118.09 (15)	C8—C7—H7A	117.00
C4—C5—C6	120.27 (15)	C7—C8—H8A	119.00
C1—C6—C5	121.43 (15)	C9—C8—H8A	119.00
C1—C7—C8	126.52 (15)	C9—C10—H10A	119.00
C7—C8—C9	122.11 (15)	C11—C10—H10A	119.00
O3—C9—C8	122.43 (14)	C10—C11—H11A	117.00
O3—C9—C10	122.50 (15)	C12—C11—H11A	117.00
C8—C9—C10	115.02 (14)	C12—C13—H13A	120.00
C9—C10—C11	121.79 (15)	C14—C13—H13A	120.00
C10—C11—C12	126.80 (15)	C13—C14—H14A	120.00
C11—C12—C13	122.53 (15)	C15—C14—H14A	120.00
C11—C12—C17	118.99 (15)	C14—C15—H15A	120.00
C13—C12—C17	118.46 (14)	C16—C15—H15A	120.00
C12—C13—C14	120.55 (16)	C15—C16—H16A	120.00
C13—C14—C15	120.36 (16)	C17—C16—H16A	120.00
C14—C15—C16	119.65 (16)	C12—C17—H17A	120.00
C15—C16—C17	120.37 (17)	C16—C17—H17A	120.00

O1—N1—C3—C2	6.3 (3)	C1—C7—C8—C9	−177.47 (17)
O1—N1—C3—C4	−172.40 (17)	C7—C8—C9—O3	−11.3 (3)
O2—N1—C3—C2	−173.88 (18)	C7—C8—C9—C10	166.11 (17)
O2—N1—C3—C4	7.4 (3)	O3—C9—C10—C11	21.9 (3)
C6—C1—C2—C3	−1.6 (3)	C8—C9—C10—C11	−155.48 (17)
C7—C1—C2—C3	177.69 (17)	C9—C10—C11—C12	176.13 (16)
C2—C1—C6—C5	0.6 (3)	C10—C11—C12—C13	10.4 (3)
C7—C1—C6—C5	−178.66 (18)	C10—C11—C12—C17	−170.91 (18)
C2—C1—C7—C8	−173.22 (18)	C11—C12—C13—C14	178.32 (17)
C6—C1—C7—C8	6.1 (3)	C17—C12—C13—C14	−0.3 (3)
C1—C2—C3—N1	−177.19 (16)	C11—C12—C17—C16	−177.90 (16)
C1—C2—C3—C4	1.5 (3)	C13—C12—C17—C16	0.8 (3)
N1—C3—C4—C5	178.43 (17)	C12—C13—C14—C15	−0.3 (3)
C2—C3—C4—C5	−0.2 (3)	C13—C14—C15—C16	0.4 (3)
C3—C4—C5—C6	−0.8 (3)	C14—C15—C16—C17	0.0 (3)
C4—C5—C6—C1	0.6 (3)	C15—C16—C17—C12	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C12–C17 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.93	2.59	3.412 (2)	147
C7—H7A···O3	0.93	2.54	2.858 (2)	100
C11—H11A···O3	0.93	2.57	2.8724 (19)	100
C5—H5A···Cg1ⁱⁱ	0.93	2.62	3.3915 (19)	141

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃NO₃
M_r	279.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.9806 (6), 9.8955 (4), 12.5562 (7)
β (°)	114.992 (7)
V (Å³)	1349.21 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.44 × 0.34 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.969, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7835, 3746, 2453
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.723

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.128, 1.02
No. of reflections	3746
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.26

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999), PARST (Nardelli, 1983) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C12–C17 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.93	2.59	3.412 (2)	147
C5—H5A···Cg1ⁱⁱ	0.93	2.62	3.3915 (19)	141

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

Acknowledgements

BN thanks the UGC for financial assistance through SAP and BSR one-time grants for the purchase of chemicals. HSY thanks the University of Mysore for research facilities. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

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Volume 68| Part 1| January 2012| Pages o74-o75

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