(E)-Ethyl 2-cyano-3-(furan-2-yl)acrylate

Kalkhambkar, R.G.; Gayathri, D.; Gupta, V.K.; Kant, R.; Jeong, Y.T.

doi:10.1107/S1600536812016510

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1482

doi:10.1107/S1600536812016510

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(E)-Ethyl 2-cyano-3-(furan-2-yl)acrylate

Rajesh G. Kalkhambkar,^a D. Gayathri,^b Vivek K. Gupta,^c Rajni Kant ^c and Yeon Tae Jeong ^d ^*

^aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad 580 001, Karnataka, India, ^bDepartment of Biotechnology, Dr. M.G.R. Educational and Research Institute, Dr. M.G.R. University, Maduravoyal, Chennai 600 095, India, ^cPost Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^dDepartment of Image Science and Engineering, Pukyong National University, Busan 608 739, Republic of Korea
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 12 April 2012; accepted 16 April 2012; online 21 April 2012)

There are two independent molecules in the asymmetric unit of the title compound, C₁₀H₉NO₃, in both of which, all non-H atoms except for the methyl C atom lie nearly in the same plane [maximum deviations = 0.094 (3) and 0.043 (2) Å]. In the crystal, each independent molecules is linked by pairs of C—H⋯O interactions, generating inversion dimers with R₂²(10) ring motifs.

Related literature

For the synthesis of related compounds, see: Yadav et al. (2004 ). For related structures, see: Wang & Jian (2008 ); Zhang et al. (2009 ); Ye et al. (2009 ); Yuvaraj et al. (2011 ).

Experimental

Crystal data

C₁₀H₉NO₃
M_r = 191.18
Monoclinic, P 2₁ /n
a = 4.6611 (2) Å
b = 19.8907 (9) Å
c = 20.9081 (9) Å
β = 91.988 (4)°
V = 1937.28 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.933, T_max = 0.990
12870 measured reflections
4568 independent reflections
2407 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.209
S = 1.04
4568 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5A—H5A⋯O2Aⁱ	0.93	2.40	3.242 (3)	151
C5B—H5B⋯O2Bⁱⁱ	0.93	2.46	3.320 (3)	153
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y, -z+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: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016510/is5119sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016510/is5119Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016510/is5119Isup3.cml

checkCIF report

Comment top

Knoevenagel condensation is an important carbon-carbon bond forming reaction in organic synthesis (Yadav et al., 2004). In continuation of our work on nitrogen and oxygen based heterocycles, we herein report the crystal structure of the title compound.

The title compound crystallizes in monoclinic system with two molecules in the asymmetric unit. Bond lengths and bond angles are comparable with the similar crystal structures solved earlier (Zhang et al., 2009; Wang & Jian, 2008; Ye et al., 2009; Yuvaraj et al., 2011). All the non-hydrogen atoms, except the methyl group, lie nearly in the same plane with a maximum out-of-plane deviation of 0.094 (3) and 0.043 (2) Å (r.m.s deviation = 0.04 and 0.024 Å), respectively, for molecules A and B. Difference in the torsion angles C7A—O3A—C8A—C9A [-167.4 (3)°] and C7B—O3B—C8B—C9B [125.3 (4)°] has been observed, indicating the flexibility of the methyl group. The crystal packing is stabilized by C—H···O intermolecular interactions generating the centrosymmetric dimer of R₂²(10) ring motif.

Related literature top

For the synthesis of related compounds, see: Yadav et al. (2004). For related structures, see: Wang & Jian (2008); Zhang et al. (2009); Ye et al. (2009); Yuvaraj et al. (2011).

Experimental top

A solution of furan-2-aldehyde (1 mol), ethyl cyanoacetate (1.2 mol) and piperidine (0.1 ml) in ethanol (20 ml) was stirred at room temperature for 8 h. After removal of the volatiles in vacuo, orange solid was obtained in quantitative yield. A sample for analysis was obtained by recrystallization from EtOAc as pale yellow needles: ¹H NMR (300 MHz, CDCl₃) δ p.p.m.: 1.42 (t, 3H, CH₃), 4.40 (q, 2H, CH₂), 6.61 (m, 1H, CH), 6.80 (m, 1H, CH), 7.28 (m, 1H, CH), 7.98 (s, 1H, HC=C).

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: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. A molecular packing view of the title compound, showing intermolecular interactions. For clarity, hydrogen atoms not involved in the hydrogen bonding have been omitted.

(E)-Ethyl 2-cyano-3-(furan-2-yl)acrylate top

Crystal data top

C₁₀H₉NO₃	F(000) = 800
M_r = 191.18	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4295 reflections
a = 4.6611 (2) Å	θ = 3.6–29.1°
b = 19.8907 (9) Å	µ = 0.10 mm⁻¹
c = 20.9081 (9) Å	T = 293 K
β = 91.988 (4)°	Needle, pale yellow
V = 1937.28 (15) Å³	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4568 independent reflections
Radiation source: fine-focus sealed tube	2407 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.1049 pixels mm^-1	θ_max = 29.2°, θ_min = 3.6°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −26→24
T_min = 0.933, T_max = 0.990	l = −27→27
12870 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.209	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0908P)² + 0.185P] where P = (F_o² + 2F_c²)/3
4568 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₀H₉NO₃	V = 1937.28 (15) Å³
M_r = 191.18	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.6611 (2) Å	µ = 0.10 mm⁻¹
b = 19.8907 (9) Å	T = 293 K
c = 20.9081 (9) Å	0.30 × 0.20 × 0.10 mm
β = 91.988 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4568 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2407 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.990	R_int = 0.034
12870 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.209	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
4568 reflections	Δρ_min = −0.24 e Å⁻³
253 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
O1A	1.1671 (4)	0.14995 (9)	0.41737 (9)	0.0642 (5)
O2A	0.5561 (4)	0.03506 (10)	0.58448 (9)	0.0724 (6)
O3A	0.8013 (4)	0.10818 (9)	0.64695 (8)	0.0617 (5)
N1A	1.2730 (5)	0.19852 (12)	0.56530 (12)	0.0695 (7)
C1A	0.9635 (5)	0.10093 (13)	0.41935 (12)	0.0524 (6)
C2A	0.9058 (6)	0.07717 (15)	0.35931 (13)	0.0658 (8)
H2A	0.7747	0.0437	0.3478	0.079*
C3A	1.0809 (7)	0.11270 (15)	0.31803 (14)	0.0709 (8)
H3A	1.0900	0.1074	0.2740	0.085*
C4A	1.2328 (7)	0.15591 (16)	0.35497 (14)	0.0747 (9)
H4A	1.3663	0.1861	0.3397	0.090*
C5A	0.8457 (5)	0.08207 (13)	0.47874 (12)	0.0520 (6)
H5A	0.7104	0.0477	0.4761	0.062*
C6A	0.9001 (5)	0.10636 (12)	0.53795 (11)	0.0468 (6)
C7A	0.7339 (6)	0.07857 (13)	0.59153 (12)	0.0516 (6)
C8A	0.6382 (7)	0.08504 (17)	0.70119 (14)	0.0781 (9)
H8A1	0.4352	0.0835	0.6894	0.094*
H8A2	0.6995	0.0402	0.7137	0.094*
C9A	0.6886 (10)	0.13165 (19)	0.75412 (17)	0.1063 (13)
H9A1	0.5820	0.1173	0.7902	0.159*
H9A2	0.6274	0.1759	0.7413	0.159*
H9A3	0.8896	0.1324	0.7658	0.159*
C10A	1.1070 (6)	0.15760 (13)	0.55250 (12)	0.0511 (6)
O1B	1.1874 (4)	0.12570 (9)	0.88858 (9)	0.0650 (5)
O2B	0.5452 (4)	−0.07433 (10)	0.94337 (10)	0.0763 (6)
O3B	0.7859 (4)	−0.11775 (9)	0.86263 (10)	0.0737 (6)
N1B	1.2343 (6)	−0.00911 (12)	0.79884 (12)	0.0752 (8)
C1B	0.9833 (5)	0.11024 (13)	0.93153 (12)	0.0526 (6)
C2B	0.9368 (6)	0.16376 (14)	0.96945 (14)	0.0654 (8)
H2B	0.8081	0.1659	1.0024	0.078*
C3B	1.1182 (7)	0.21538 (15)	0.95001 (15)	0.0717 (8)
H3B	1.1340	0.2584	0.9672	0.086*
C4B	1.2645 (7)	0.19017 (15)	0.90153 (17)	0.0732 (8)
H4B	1.4018	0.2139	0.8795	0.088*
C5B	0.8538 (5)	0.04531 (13)	0.93108 (12)	0.0545 (7)
H5B	0.7222	0.0384	0.9629	0.065*
C6B	0.8908 (5)	−0.00742 (13)	0.89236 (11)	0.0492 (6)
C7B	0.7208 (6)	−0.06891 (14)	0.90287 (13)	0.0571 (7)
C8B	0.6333 (9)	−0.18142 (18)	0.86891 (18)	0.0999 (12)
H8B1	0.7679	−0.2160	0.8829	0.120*
H8B2	0.4903	−0.1769	0.9013	0.120*
C9B	0.4999 (11)	−0.2007 (2)	0.8116 (2)	0.1386 (19)
H9B1	0.4030	−0.2428	0.8173	0.208*
H9B2	0.6412	−0.2057	0.7796	0.208*
H9B3	0.3631	−0.1671	0.7981	0.208*
C10B	1.0847 (6)	−0.00751 (13)	0.84084 (12)	0.0541 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0780 (12)	0.0690 (13)	0.0461 (11)	−0.0191 (10)	0.0102 (9)	−0.0059 (9)
O2A	0.0919 (14)	0.0708 (13)	0.0550 (12)	−0.0275 (11)	0.0091 (10)	0.0000 (10)
O3A	0.0759 (12)	0.0698 (12)	0.0399 (10)	−0.0140 (10)	0.0093 (8)	−0.0011 (8)
N1A	0.0813 (16)	0.0642 (16)	0.0636 (16)	−0.0126 (14)	0.0113 (13)	−0.0078 (12)
C1A	0.0597 (15)	0.0511 (15)	0.0467 (15)	0.0011 (12)	0.0061 (11)	−0.0023 (11)
C2A	0.0812 (19)	0.0655 (18)	0.0510 (16)	−0.0147 (15)	0.0053 (14)	−0.0076 (13)
C3A	0.091 (2)	0.079 (2)	0.0434 (16)	−0.0073 (17)	0.0117 (15)	−0.0046 (14)
C4A	0.095 (2)	0.081 (2)	0.0499 (17)	−0.0172 (17)	0.0225 (16)	−0.0014 (15)
C5A	0.0601 (15)	0.0480 (15)	0.0480 (15)	−0.0011 (12)	0.0049 (11)	−0.0014 (11)
C6A	0.0537 (14)	0.0419 (14)	0.0450 (14)	0.0002 (11)	0.0042 (11)	−0.0007 (10)
C7A	0.0632 (16)	0.0495 (15)	0.0421 (14)	−0.0021 (13)	0.0044 (11)	0.0029 (11)
C8A	0.098 (2)	0.091 (2)	0.0464 (17)	−0.0161 (18)	0.0209 (15)	0.0028 (15)
C9A	0.150 (4)	0.111 (3)	0.060 (2)	−0.021 (3)	0.036 (2)	−0.0106 (19)
C10A	0.0634 (15)	0.0515 (16)	0.0390 (13)	0.0055 (13)	0.0098 (11)	0.0003 (11)
O1B	0.0693 (12)	0.0633 (13)	0.0633 (13)	−0.0045 (10)	0.0132 (9)	−0.0107 (9)
O2B	0.0828 (14)	0.0810 (14)	0.0665 (14)	−0.0095 (11)	0.0257 (11)	0.0105 (11)
O3B	0.1015 (15)	0.0592 (12)	0.0617 (13)	−0.0246 (11)	0.0199 (11)	−0.0061 (10)
N1B	0.0915 (18)	0.0755 (18)	0.0601 (16)	−0.0159 (14)	0.0255 (14)	−0.0079 (13)
C1B	0.0568 (15)	0.0572 (17)	0.0438 (14)	0.0064 (13)	0.0024 (11)	−0.0014 (11)
C2B	0.0736 (18)	0.0630 (19)	0.0596 (18)	0.0083 (15)	0.0041 (14)	−0.0094 (14)
C3B	0.085 (2)	0.0586 (18)	0.071 (2)	0.0061 (16)	−0.0049 (16)	−0.0118 (15)
C4B	0.0759 (19)	0.0613 (19)	0.083 (2)	−0.0098 (16)	0.0064 (16)	−0.0059 (16)
C5B	0.0578 (15)	0.0630 (18)	0.0429 (15)	0.0028 (13)	0.0027 (11)	0.0000 (12)
C6B	0.0553 (14)	0.0531 (15)	0.0392 (13)	−0.0010 (12)	0.0028 (10)	0.0030 (11)
C7B	0.0659 (17)	0.0623 (17)	0.0433 (15)	−0.0005 (14)	0.0016 (12)	0.0049 (13)
C8B	0.151 (3)	0.075 (2)	0.074 (2)	−0.051 (2)	0.011 (2)	0.0059 (18)
C9B	0.220 (5)	0.098 (3)	0.096 (3)	−0.083 (3)	−0.014 (3)	0.009 (2)
C10B	0.0702 (17)	0.0485 (15)	0.0438 (15)	−0.0059 (12)	0.0039 (12)	−0.0017 (11)

Geometric parameters (Å, º) top

O1A—C4A	1.356 (3)	O1B—C4B	1.357 (3)
O1A—C1A	1.362 (3)	O1B—C1B	1.366 (3)
O2A—C7A	1.204 (3)	O2B—C7B	1.203 (3)
O3A—C7A	1.328 (3)	O3B—C7B	1.327 (3)
O3A—C8A	1.461 (3)	O3B—C8B	1.461 (4)
N1A—C10A	1.148 (3)	N1B—C10B	1.140 (3)
C1A—C2A	1.360 (3)	C1B—C2B	1.349 (4)
C1A—C5A	1.425 (3)	C1B—C5B	1.425 (4)
C2A—C3A	1.400 (4)	C2B—C3B	1.399 (4)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.341 (4)	C3B—C4B	1.338 (4)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.345 (3)	C5B—C6B	1.340 (3)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C10A	1.429 (4)	C6B—C10B	1.430 (3)
C6A—C7A	1.490 (3)	C6B—C7B	1.478 (4)
C8A—C9A	1.457 (4)	C8B—C9B	1.385 (5)
C8A—H8A1	0.9700	C8B—H8B1	0.9700
C8A—H8A2	0.9700	C8B—H8B2	0.9700
C9A—H9A1	0.9600	C9B—H9B1	0.9600
C9A—H9A2	0.9600	C9B—H9B2	0.9600
C9A—H9A3	0.9600	C9B—H9B3	0.9600

C4A—O1A—C1A	105.8 (2)	C4B—O1B—C1B	105.5 (2)
C7A—O3A—C8A	115.1 (2)	C7B—O3B—C8B	117.1 (2)
C2A—C1A—O1A	109.7 (2)	C2B—C1B—O1B	109.8 (2)
C2A—C1A—C5A	130.0 (3)	C2B—C1B—C5B	130.0 (3)
O1A—C1A—C5A	120.3 (2)	O1B—C1B—C5B	120.3 (2)
C1A—C2A—C3A	107.0 (3)	C1B—C2B—C3B	107.3 (3)
C1A—C2A—H2A	126.5	C1B—C2B—H2B	126.4
C3A—C2A—H2A	126.5	C3B—C2B—H2B	126.4
C4A—C3A—C2A	106.0 (3)	C4B—C3B—C2B	105.9 (3)
C4A—C3A—H3A	127.0	C4B—C3B—H3B	127.1
C2A—C3A—H3A	127.0	C2B—C3B—H3B	127.1
C3A—C4A—O1A	111.5 (3)	C3B—C4B—O1B	111.5 (3)
C3A—C4A—H4A	124.3	C3B—C4B—H4B	124.2
O1A—C4A—H4A	124.3	O1B—C4B—H4B	124.2
C6A—C5A—C1A	129.9 (2)	C6B—C5B—C1B	130.5 (2)
C6A—C5A—H5A	115.1	C6B—C5B—H5B	114.7
C1A—C5A—H5A	115.1	C1B—C5B—H5B	114.7
C5A—C6A—C10A	123.8 (2)	C5B—C6B—C10B	123.7 (2)
C5A—C6A—C7A	118.2 (2)	C5B—C6B—C7B	118.5 (2)
C10A—C6A—C7A	118.0 (2)	C10B—C6B—C7B	117.9 (2)
O2A—C7A—O3A	124.5 (2)	O2B—C7B—O3B	123.8 (3)
O2A—C7A—C6A	123.2 (2)	O2B—C7B—C6B	124.1 (3)
O3A—C7A—C6A	112.2 (2)	O3B—C7B—C6B	112.1 (2)
C9A—C8A—O3A	108.3 (3)	C9B—C8B—O3B	111.6 (3)
C9A—C8A—H8A1	110.0	C9B—C8B—H8B1	109.3
O3A—C8A—H8A1	110.0	O3B—C8B—H8B1	109.3
C9A—C8A—H8A2	110.0	C9B—C8B—H8B2	109.3
O3A—C8A—H8A2	110.0	O3B—C8B—H8B2	109.3
H8A1—C8A—H8A2	108.4	H8B1—C8B—H8B2	108.0
C8A—C9A—H9A1	109.5	C8B—C9B—H9B1	109.5
C8A—C9A—H9A2	109.5	C8B—C9B—H9B2	109.5
H9A1—C9A—H9A2	109.5	H9B1—C9B—H9B2	109.5
C8A—C9A—H9A3	109.5	C8B—C9B—H9B3	109.5
H9A1—C9A—H9A3	109.5	H9B1—C9B—H9B3	109.5
H9A2—C9A—H9A3	109.5	H9B2—C9B—H9B3	109.5
N1A—C10A—C6A	178.8 (3)	N1B—C10B—C6B	177.9 (3)

C4A—O1A—C1A—C2A	0.1 (3)	C4B—O1B—C1B—C2B	0.1 (3)
C4A—O1A—C1A—C5A	−179.9 (2)	C4B—O1B—C1B—C5B	179.8 (2)
O1A—C1A—C2A—C3A	0.1 (3)	O1B—C1B—C2B—C3B	0.0 (3)
C5A—C1A—C2A—C3A	−179.9 (3)	C5B—C1B—C2B—C3B	−179.7 (3)
C1A—C2A—C3A—C4A	−0.3 (3)	C1B—C2B—C3B—C4B	−0.1 (3)
C2A—C3A—C4A—O1A	0.4 (4)	C2B—C3B—C4B—O1B	0.2 (4)
C1A—O1A—C4A—C3A	−0.3 (4)	C1B—O1B—C4B—C3B	−0.2 (3)
C2A—C1A—C5A—C6A	−178.9 (3)	C2B—C1B—C5B—C6B	177.4 (3)
O1A—C1A—C5A—C6A	1.1 (4)	O1B—C1B—C5B—C6B	−2.2 (4)
C1A—C5A—C6A—C10A	−2.1 (4)	C1B—C5B—C6B—C10B	0.5 (4)
C1A—C5A—C6A—C7A	177.5 (2)	C1B—C5B—C6B—C7B	−179.0 (2)
C8A—O3A—C7A—O2A	−1.0 (4)	C8B—O3B—C7B—O2B	−0.2 (4)
C8A—O3A—C7A—C6A	177.8 (2)	C8B—O3B—C7B—C6B	179.4 (3)
C5A—C6A—C7A—O2A	0.8 (4)	C5B—C6B—C7B—O2B	1.7 (4)
C10A—C6A—C7A—O2A	−179.5 (2)	C10B—C6B—C7B—O2B	−177.8 (3)
C5A—C6A—C7A—O3A	−178.0 (2)	C5B—C6B—C7B—O3B	−177.9 (2)
C10A—C6A—C7A—O3A	1.6 (3)	C10B—C6B—C7B—O3B	2.6 (3)
C7A—O3A—C8A—C9A	−167.4 (3)	C7B—O3B—C8B—C9B	125.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A···O2Aⁱ	0.93	2.40	3.242 (3)	151
C5B—H5B···O2Bⁱⁱ	0.93	2.46	3.320 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₃
M_r	191.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	4.6611 (2), 19.8907 (9), 20.9081 (9)
β (°)	91.988 (4)
V (Å³)	1937.28 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.933, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	12870, 4568, 2407
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.209, 1.04
No. of reflections	4568
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.24

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A···O2Aⁱ	0.93	2.40	3.242 (3)	151
C5B—H5B···O2Bⁱⁱ	0.93	2.46	3.320 (3)	153

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

Acknowledgements

YTJ is thankful for the support provided by the second stage of the BK-21 program. The authors thank the Director, USIC University of Jammu, Jammu Tawi, India, for the X-ray data collection.

References

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