(E)-3-(2-Chloro­phen­yl)-1-(4-nitro­phen­yl)prop-2-en-1-one

Fun, H.-K.; Chantrapromma, S.; Patil, P.S.; Dharmaprakash, S.M.

doi:10.1107/S160053680801218X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o958-o959

doi:10.1107/S160053680801218X

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(E)-3-(2-Chlorophenyl)-1-(4-nitrophenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ‡ P. S. Patil ^c and S. M. Dharmaprakash ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 24 April 2008; accepted 27 April 2008; online 3 May 2008)

In the title compound, C₁₅H₁₀ClNO₃, a substituted chalcone, the 2-chlorophenyl and 4-nitrophenyl rings make a dihedral angle of 26.48 (6)°. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Weak intramolecular C—H⋯O and C—H⋯Cl interactions involving the enone groups generate S(5) ring motifs, which help to stabilize the planarity of the 3-(2-chlorophenyl)prop-2-en-1-one segment of the molecule. In the crystal structure, adjacent molecules are stacked in a head-to-tail fashion into columns along the a axis by π–π interactions [centroid–centroid distance = 3.6955 (8) Å]. Neighbouring columns are linked by weak C—H⋯O interactions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see, for example: Fun et al. (2007 ); Patil et al. (2006b ; 2007a ,b ,c ). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ); Gu et al. (2008 ); Patil et al. (2006a , 2007c,d ).

Experimental

Crystal data

C₁₅H₁₀ClNO₃
M_r = 287.69
Monoclinic, C 2/c
a = 13.7003 (2) Å
b = 7.3659 (1) Å
c = 25.9954 (4) Å
β = 102.290 (1)°
V = 2563.21 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100.0 (1) K
0.36 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.899, T_max = 0.957
27534 measured reflections
3736 independent reflections
3008 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.103
S = 1.07
3736 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.93	2.58	3.4284 (18)	152
C5—H5⋯O1ⁱⁱ	0.93	2.59	3.2996 (17)	134
C7—H7⋯Cl1	0.93	2.60	3.0531 (14)	110
C7—H7⋯O1	0.93	2.47	2.7981 (16)	101
C12—H12⋯O1ⁱⁱⁱ	0.93	2.56	3.3298 (17)	141
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801218X/sj2489sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801218X/sj2489Isup2.hkl

checkCIF report

Comment top

Chalcone derivatives have been extensively studied in attempts to obtain non-linear optical (NLO) materials (Agrinskaya et al., 1999; Patil et al., 2006a, 2007c, 2007d). We have previously synthesized and crystallized several chalcone derivatives to study their non-linear optical properties (Agrinskaya et al., 1999; Fun et al., 2007; Patil et al., 2006a, 2007a, 2007b, 2007c, 2007d). As part of our studies on structure-property relationships of chalcones and the importance of substituted chalcones in nonlinear optics (Agrinskaya et al., 1999; Patil et al., 2006a, 2007c, 2007d), the title compound was synthesized and its crystal structure is reported here. Unfortunately this crystal does not have second-order NLO properties because it crystallizes in the centrosymmetric C2/c space group.

The molecular structure of the title compound (Fig. 1) is not planar as indicated by the dihedral angle between the 4-nitrobenzene and 2-chlorobenzene rings being 26.48 (6)°. The propene unit (C7/C8/C9) is co-planar with the 2-chlorobenzene ring with the torsion angle C6–C7–C8–C9 = -178.41 (12)°. Atoms O1, C8, C9 and C10 lie on a plane and the least-squares plane through this moiety makes dihedral angles of 8.69 (7)° and 26.48 (6)° with the 4-nitrobenzene and 2-chlorolbenzene rings, repectively. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Bond lengths and angles shown normal values (Allen et al., 1987) and are comparable to those in related structures (Fun et al., 2007; Patil et al., 2006b; 2007a; 2007b; 2007c; 2007d). In the structure of the title compound, weak intramolecular C7—H7···O1 and C7—H7···Cl1 interactions generate S(5) ring motifs (Bernstein et al., 1995) (Fig. 1 and Table 1) which help to stabilize the planarity of the (2-chlorophenyl)prop-2-en-1-one segment of the molecule.

In the crystal structure (Fig. 2), adjacent molecules are stacked in a head to tail fashion into columns along the a-axis by π···π interactions with the distances of Cg₁···Cg₂ = 3.6955 (8) Å: symmetry code 1/2 - x, 1/2 + y, 1/2 - z Cg₁ and Cg₂ are the centroids of C1–C6 and C10–C15, respectively. The neighbouring columns are linked by weak C—H···O interactions (Table 1).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see, for example: Fun et al. (2007); Patil et al. (2006b; 2007a,b,c). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999); Gu et al. (2008); Patil et al. (2006a, 2007c,d).

Experimental top

The title compound was synthesized by the condensation of 2-chlorobenzaldehyde (0.01 mol) with 4-nitroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 4 hr, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 hr. The resulting crude solid was filtered and dried. Colorless single crystals of the title compound suitable for x-ray structure determination were recrystallized from N,N-dimethylformamide (DMF).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Weak intramolecular C—H···O and C—H···Cl interactions are drawn as dashed lines.
	Fig. 2. The crystal packing of (I), viewed along the b axis showing the stacking of the molecules along the a axis. Hydrogen bonds are drawn as dashed lines.

(E)-3-(2-Chlorophenyl)-1-(4-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀ClNO₃	F(000) = 1184
M_r = 287.69	D_x = 1.491 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3736 reflections
a = 13.7003 (2) Å	θ = 1.6–30.0°
b = 7.3659 (1) Å	µ = 0.30 mm⁻¹
c = 25.9954 (4) Å	T = 100 K
β = 102.290 (1)°	Block, colorless
V = 2563.21 (7) Å³	0.36 × 0.22 × 0.14 mm
Z = 8

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	3736 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.6°
ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
T_min = 0.899, T_max = 0.957	l = −36→36
27534 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0472P)² + 1.7337P] where P = (F_o² + 2F_c²)/3
3736 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₀ClNO₃	V = 2563.21 (7) Å³
M_r = 287.69	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 13.7003 (2) Å	µ = 0.30 mm⁻¹
b = 7.3659 (1) Å	T = 100 K
c = 25.9954 (4) Å	0.36 × 0.22 × 0.14 mm
β = 102.290 (1)°

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	3736 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3008 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.957	R_int = 0.043
27534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.07	Δρ_max = 0.42 e Å⁻³
3736 reflections	Δρ_min = −0.26 e Å⁻³
181 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment

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
Cl1	0.51146 (3)	1.13027 (5)	0.327931 (14)	0.02471 (10)
O1	0.26191 (7)	0.90593 (14)	0.17879 (4)	0.0253 (2)
O2	0.07873 (8)	0.27115 (15)	−0.01091 (4)	0.0305 (3)
O3	0.18728 (9)	0.07688 (15)	0.02905 (4)	0.0321 (3)
N1	0.14644 (9)	0.22581 (17)	0.02587 (4)	0.0224 (2)
C1	0.51251 (10)	0.91188 (19)	0.35378 (5)	0.0193 (3)
C2	0.57265 (10)	0.8810 (2)	0.40322 (5)	0.0227 (3)
H2	0.6106	0.9747	0.4213	0.027*
C3	0.57562 (10)	0.7097 (2)	0.42526 (5)	0.0235 (3)
H3	0.6157	0.6881	0.4583	0.028*
C4	0.51884 (10)	0.5699 (2)	0.39809 (6)	0.0228 (3)
H4	0.5207	0.4548	0.4130	0.027*
C5	0.45951 (10)	0.60253 (19)	0.34883 (5)	0.0210 (3)
H5	0.4218	0.5080	0.3310	0.025*
C6	0.45467 (9)	0.77387 (18)	0.32502 (5)	0.0181 (3)
C7	0.39252 (9)	0.80876 (19)	0.27284 (5)	0.0191 (3)
H7	0.3918	0.9272	0.2604	0.023*
C8	0.33667 (10)	0.68819 (19)	0.24123 (5)	0.0211 (3)
H8	0.3334	0.5685	0.2521	0.025*
C9	0.28008 (9)	0.74551 (18)	0.18885 (5)	0.0183 (3)
C10	0.24532 (9)	0.60468 (18)	0.14738 (5)	0.0173 (3)
C11	0.27549 (9)	0.42431 (19)	0.15364 (5)	0.0192 (3)
H11	0.3174	0.3876	0.1849	0.023*
C12	0.24381 (10)	0.29833 (19)	0.11385 (5)	0.0198 (3)
H12	0.2642	0.1778	0.1178	0.024*
C13	0.18098 (9)	0.35820 (18)	0.06821 (5)	0.0181 (3)
C14	0.14839 (10)	0.53630 (19)	0.06062 (5)	0.0206 (3)
H14	0.1051	0.5715	0.0296	0.025*
C15	0.18190 (10)	0.65985 (19)	0.10033 (5)	0.0203 (3)
H15	0.1622	0.7807	0.0958	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02953 (18)	0.01723 (17)	0.02609 (18)	−0.00492 (13)	0.00304 (13)	−0.00086 (13)
O1	0.0278 (5)	0.0189 (5)	0.0263 (5)	0.0027 (4)	−0.0008 (4)	−0.0011 (4)
O2	0.0343 (6)	0.0307 (6)	0.0211 (5)	−0.0001 (5)	−0.0059 (4)	−0.0018 (5)
O3	0.0397 (6)	0.0234 (5)	0.0297 (6)	0.0052 (5)	−0.0002 (5)	−0.0072 (5)
N1	0.0254 (6)	0.0224 (6)	0.0188 (5)	−0.0022 (5)	0.0034 (4)	−0.0015 (5)
C1	0.0208 (6)	0.0175 (6)	0.0202 (6)	0.0004 (5)	0.0056 (5)	−0.0017 (5)
C2	0.0230 (6)	0.0246 (7)	0.0195 (6)	−0.0026 (5)	0.0025 (5)	−0.0050 (5)
C3	0.0221 (6)	0.0297 (8)	0.0181 (6)	0.0043 (6)	0.0028 (5)	−0.0015 (6)
C4	0.0242 (6)	0.0214 (7)	0.0227 (7)	0.0031 (5)	0.0049 (5)	0.0026 (5)
C5	0.0223 (6)	0.0185 (6)	0.0215 (6)	−0.0013 (5)	0.0032 (5)	−0.0005 (5)
C6	0.0175 (5)	0.0183 (6)	0.0188 (6)	−0.0002 (5)	0.0043 (5)	−0.0016 (5)
C7	0.0199 (6)	0.0165 (6)	0.0209 (6)	−0.0003 (5)	0.0042 (5)	0.0006 (5)
C8	0.0271 (6)	0.0170 (6)	0.0179 (6)	−0.0020 (5)	0.0019 (5)	0.0006 (5)
C9	0.0179 (5)	0.0180 (6)	0.0191 (6)	−0.0005 (5)	0.0042 (5)	0.0000 (5)
C10	0.0162 (5)	0.0184 (6)	0.0171 (6)	−0.0004 (5)	0.0034 (4)	0.0010 (5)
C11	0.0188 (6)	0.0205 (6)	0.0166 (6)	0.0006 (5)	0.0000 (5)	0.0018 (5)
C12	0.0218 (6)	0.0171 (6)	0.0197 (6)	0.0020 (5)	0.0026 (5)	0.0007 (5)
C13	0.0188 (6)	0.0193 (6)	0.0159 (6)	−0.0018 (5)	0.0032 (4)	−0.0015 (5)
C14	0.0219 (6)	0.0205 (7)	0.0175 (6)	0.0021 (5)	0.0003 (5)	0.0031 (5)
C15	0.0218 (6)	0.0182 (6)	0.0195 (6)	0.0013 (5)	0.0017 (5)	0.0029 (5)

Geometric parameters (Å, º) top

Cl1—C1	1.7422 (14)	C7—C8	1.3348 (19)
O1—C9	1.2243 (16)	C7—H7	0.9300
O2—N1	1.2283 (15)	C8—C9	1.4777 (18)
O3—N1	1.2263 (16)	C8—H8	0.9300
N1—C13	1.4712 (17)	C9—C10	1.4989 (18)
C1—C2	1.3898 (19)	C10—C11	1.3906 (19)
C1—C6	1.4029 (18)	C10—C15	1.4012 (18)
C2—C3	1.382 (2)	C11—C12	1.3886 (19)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.389 (2)	C12—C13	1.3814 (18)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.3839 (19)	C13—C14	1.3863 (19)
C4—H4	0.9300	C14—C15	1.3795 (19)
C5—C6	1.4010 (19)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.4627 (18)

O3—N1—O2	123.63 (12)	C7—C8—C9	119.78 (13)
O3—N1—C13	118.24 (11)	C7—C8—H8	120.1
O2—N1—C13	118.13 (12)	C9—C8—H8	120.1
C2—C1—C6	122.04 (13)	O1—C9—C8	121.04 (12)
C2—C1—Cl1	117.55 (11)	O1—C9—C10	119.69 (12)
C6—C1—Cl1	120.41 (10)	C8—C9—C10	119.28 (12)
C3—C2—C1	119.48 (13)	C11—C10—C15	119.53 (12)
C3—C2—H2	120.3	C11—C10—C9	122.41 (11)
C1—C2—H2	120.3	C15—C10—C9	118.04 (12)
C2—C3—C4	120.10 (13)	C12—C11—C10	120.88 (12)
C2—C3—H3	119.9	C12—C11—H11	119.6
C4—C3—H3	119.9	C10—C11—H11	119.6
C5—C4—C3	119.79 (14)	C13—C12—C11	117.72 (13)
C5—C4—H4	120.1	C13—C12—H12	121.1
C3—C4—H4	120.1	C11—C12—H12	121.1
C4—C5—C6	121.89 (13)	C12—C13—C14	123.19 (13)
C4—C5—H5	119.1	C12—C13—N1	118.25 (12)
C6—C5—H5	119.1	C14—C13—N1	118.56 (12)
C5—C6—C1	116.69 (12)	C15—C14—C13	118.16 (12)
C5—C6—C7	122.10 (12)	C15—C14—H14	120.9
C1—C6—C7	121.21 (12)	C13—C14—H14	120.9
C8—C7—C6	126.75 (13)	C14—C15—C10	120.51 (13)
C8—C7—H7	116.6	C14—C15—H15	119.7
C6—C7—H7	116.6	C10—C15—H15	119.7

C6—C1—C2—C3	−0.4 (2)	C8—C9—C10—C11	−8.89 (19)
Cl1—C1—C2—C3	179.90 (10)	O1—C9—C10—C15	−7.99 (19)
C1—C2—C3—C4	0.0 (2)	C8—C9—C10—C15	172.55 (12)
C2—C3—C4—C5	0.2 (2)	C15—C10—C11—C12	0.2 (2)
C3—C4—C5—C6	0.1 (2)	C9—C10—C11—C12	−178.36 (12)
C4—C5—C6—C1	−0.5 (2)	C10—C11—C12—C13	−0.5 (2)
C4—C5—C6—C7	179.65 (13)	C11—C12—C13—C14	−0.2 (2)
C2—C1—C6—C5	0.67 (19)	C11—C12—C13—N1	−179.66 (12)
Cl1—C1—C6—C5	−179.69 (10)	O3—N1—C13—C12	−11.92 (19)
C2—C1—C6—C7	−179.46 (12)	O2—N1—C13—C12	168.59 (12)
Cl1—C1—C6—C7	0.19 (18)	O3—N1—C13—C14	168.59 (13)
C5—C6—C7—C8	−2.1 (2)	O2—N1—C13—C14	−10.89 (19)
C1—C6—C7—C8	178.04 (13)	C12—C13—C14—C15	1.1 (2)
C6—C7—C8—C9	−178.41 (12)	N1—C13—C14—C15	−179.41 (12)
C7—C8—C9—O1	−19.1 (2)	C13—C14—C15—C10	−1.4 (2)
C7—C8—C9—C10	160.38 (12)	C11—C10—C15—C14	0.8 (2)
O1—C9—C10—C11	170.56 (13)	C9—C10—C15—C14	179.38 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.58	3.4284 (18)	152
C5—H5···O1ⁱⁱ	0.93	2.59	3.2996 (17)	134
C7—H7···Cl1	0.93	2.60	3.0531 (14)	110
C7—H7···O1	0.93	2.47	2.7981 (16)	101
C12—H12···O1ⁱⁱⁱ	0.93	2.56	3.3298 (17)	141

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClNO₃
M_r	287.69
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	13.7003 (2), 7.3659 (1), 25.9954 (4)
β (°)	102.290 (1)
V (Å³)	2563.21 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.36 × 0.22 × 0.14

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.899, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	27534, 3736, 3008
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.103, 1.07
No. of reflections	3736
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.58	3.4284 (18)	152
C5—H5···O1ⁱⁱ	0.93	2.59	3.2996 (17)	134
C7—H7···Cl1	0.93	2.60	3.0531 (14)	110
C7—H7···O1	0.93	2.47	2.7981 (16)	101
C12—H12···O1ⁱⁱⁱ	0.93	2.56	3.3298 (17)	141

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

PSP thanks the DRDO, Government of India, for a Senior Research Fellowship (SRF). This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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