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

Dutkiewicz, G.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.; Kubicki, M.

doi:10.1107/S1600536809050508

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3255-o3256

doi:10.1107/S1600536809050508

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

Grzegorz Dutkiewicz,^a S. Samshuddin,^b B. Narayana,^b H. S. Yathirajan ^c and Maciej Kubicki ^a ^*

^aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Mysore 570 006, India
^*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 13 November 2009; accepted 24 November 2009; online 28 November 2009)

In the title compound, C₁₉H₁₃ClO, the benzene ring and the naphthalene system, are twisted by 12.3 (3) and 36.1 (2)°, respectively, and in opposite directions with respect to the central propenone bridge. The bond-angle pattern within the benzene ring is influence by both substituents; these influences are almost additive. In the crystal, the molecules are linked by C—H⋯O and C—H⋯Cl interactions.

Related literature

For chalcones, see: Dhar (1981 ); Di Carlo et al. (1999 ); Dimmock et al. (1999 ); Goto et al. (1991 ); Indira et al. (2002 ); Sarojini et al. (2006 ); Satyanarayana et al. (2004 ); Uchida et al. (1998 ); Yarishkin (2008 ). For the 1-naphtyl analogue, see: Eswaramoorthy et al. (1994 ). For the influence of substituents on the geometry of the phenyl ring, see: Domenicano (1988 $[Domenicano, A. (1988). In Stereochemical Applications of gas-phase electron diffraction, edited by I. Hargittai & M. Hargittai, pp. 281-324. New York: VCH.]$ ). For a description of the Cambridge Crystallographic Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₉H₁₃ClO
M_r = 292.74
Monoclinic, P c
a = 12.0392 (14) Å
b = 8.0544 (5) Å
c = 7.8472 (6) Å
β = 98.091 (10)°
V = 753.36 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.666, T_max = 1.000
2481 measured reflections
1866 independent reflections
1440 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.083
S = 0.96
1866 reflections
190 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ), 423 Friedel pairs
Flack parameter: 0.08 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O12ⁱ	0.93	2.42	3.180 (4)	139
C3—H3⋯Cl21ⁱⁱ	0.93	2.92	3.703 (3)	143
C8—H8⋯O12ⁱⁱⁱ	0.93	2.64	3.546 (4)	163
Symmetry codes: (i) x, y+1, z; (ii) $[x-1, -y+2, z-{\script{1\over 2}}]$ ; (iii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050508/fk2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050508/fk2008Isup2.hkl

checkCIF report

Comment top

Chalcones constitute an important family of flavonoids. 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). Some chalcones demonstrated the ability to block voltage-dependent potassium channels (Yarishkin et al., 2008). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006). Chalcone derivatives are recognized material in the NLO applications because of their excellent blue light transmittance and good crystallization ability (Goto et al.,1991; Uchida et al.,1998; Indira et al., 2002). Chemically chalcones consists of open-chain flavonoids in which the two aromatic rings are joined by α,\&s-unsaturated carbonyl system. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using these compounds or chalcone rich plant extracts as drugs or food preservatives (Di Carlo et al., 1999). As a part of our efforts on the synthesis of naphthyl chalcones, this paper describes the crystal structure of a new naphthyl chalcone, (2E)-3-(4-Chlorophenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (I, Scheme 1). There are 298 structures in the Cambridge Crystallographic Database (Allen, 2002: Ver. 5.30, Nov. 2008, last update Sep. 2009) that posses two aromatic moieties connected via CH=CH—CO– fragment, but only 10 of them are naphthyl chalcones, and the single one example with 1-naphthalene substituent (1-(1-Naphthalenyl)-3-(4-nitrophenyl)-2-propenone, Eswaramoorthy et al., 1994). It might be noted, that this structure apparently has errors: one of the torsion angles in the aromatic ring is as large as 5°.

The molecule of I is built of three approximately planar fragments (Fig. 1): the phenyl ring (A, maximum deviation form the least-squares plane is 0.006 (3) Å), propenone fragment C=C—C=O (B, 0.014 (2) Å), and the naphtalene ring system (C). This last fragment however is significantly folded, even though both individual rings are almost planar, the dihedral angle between these planes is as high as 5.05 (13)°. The overall conformation of I can be described in terms of dihedral angles between these fragments: A/B 36.1 (2)°, B/C 12.3 (3)°, and A/C 25.51 (9)°. These values show that the terminal planes are twisted in opposite sense with respect to the central bridging fragment. This situation is relatively rare, the majority of chalcones found in the CDB shows the same sense of rotation with respect to the central bridge.

The bond lengths within the conjugated linear fragment suggest the large degree of localization: C—C bond length of 1.480 (4) Å, C=C of 1.329 (4)Å and C=O 1.232 (3) Å. The bond angles within the phenyl ring are influenced by both Cl and C=C– substituents, and these influences are almost additive, as suggested e.g., by Domenicano (1988). The distribution is almost symmetrical with respect to the C15···C18 line, and the values are close to those calculated by summing the effects of both substituents.

In the crystal structure there is one relatively short C—H···O potential hydrogen bond, C17—H17···O12(x,1 + y,z), that link molecules into infinite chains along y direction, and few weak C—H···O and C—H···π contacts, which can stabilize the packing otherwise determined by the van der Waals interactions and close packing requirements (Fig. 2).

Related literature top

For chalcones, see: Dhar (1981); Di Carlo et al. (1999); Dimmock et al. (1999); Goto et al. (1991); Indira et al. (2002); Sarojini et al. (2006); Satyanarayana et al. (2004); Uchida et al. (1998); Yarishkin (2008). For the 1-naphtyl analogue, see: Eswaramoorthy et al. (1994). For the influence of substituents on the geometry of the phenyl ring, see: Domenicano (1988). For a description of the Cambridge Crystallographic Database, see: Allen (2002).

Experimental top

To a mixture of 1-acetonaphthone (1.7 g, 0.01 mol) and p-chlorobenzaldehyde (1.4 g, 0.01 mol) in 30 ml e thanol, 10 ml of 10% sodium hydroxide solution was added and stirred at 5–10 ^oC for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from DMF by slow evaporation method and yield of the compound was 82%. (m.p. 360–362 K). Analytical data: Found (Calculated): C %: 76.89 (77.95); H %: 4.23 (4.48).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Anisotropic ellipsoid representation of the compound I together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii.
	Fig. 2. The crystal packing of I as seen along z direction; weak C—H···O bonds are shown as dashed lines.
	Fig. 3. The formation of the title compound.

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

Crystal data top

C₁₉H₁₃ClO	F(000) = 304
M_r = 292.74	D_x = 1.291 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 1288 reflections
a = 12.0392 (14) Å	θ = 2.5–26.6°
b = 8.0544 (5) Å	µ = 0.25 mm⁻¹
c = 7.8472 (6) Å	T = 295 K
β = 98.091 (10)°	Block, colourless
V = 753.36 (11) Å³	0.30 × 0.20 × 0.15 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer	1866 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1440 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Detector resolution: 8.1929 pixels mm^-1	θ_max = 26.6°, θ_min = 2.5°
ω scan	h = −14→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→4
T_min = 0.667, T_max = 1.000	l = −9→6
2481 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.050P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.001
1866 reflections	Δρ_max = 0.12 e Å⁻³
190 parameters	Δρ_min = −0.13 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 423 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (7)

Crystal data top

C₁₉H₁₃ClO	V = 753.36 (11) Å³
M_r = 292.74	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 12.0392 (14) Å	µ = 0.25 mm⁻¹
b = 8.0544 (5) Å	T = 295 K
c = 7.8472 (6) Å	0.30 × 0.20 × 0.15 mm
β = 98.091 (10)°

Data collection top

Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer	1866 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1440 reflections with I > 2σ(I)
T_min = 0.667, T_max = 1.000	R_int = 0.014
2481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.083	Δρ_max = 0.12 e Å⁻³
S = 0.96	Δρ_min = −0.13 e Å⁻³
1866 reflections	Absolute structure: Flack (1983), 423 Friedel pairs
190 parameters	Absolute structure parameter: 0.08 (7)
2 restraints

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
C1	0.0117 (2)	0.4299 (3)	0.5052 (3)	0.0451 (6)
C2	−0.0556 (2)	0.5690 (3)	0.4967 (3)	0.0543 (7)
H2	−0.0256	0.6681	0.5435	0.065*
C3	−0.1681 (2)	0.5651 (4)	0.4195 (4)	0.0618 (7)
H3	−0.2119	0.6605	0.4154	0.074*
C4	−0.2124 (2)	0.4207 (4)	0.3508 (4)	0.0617 (7)
H4	−0.2879	0.4175	0.3048	0.074*
C5	−0.1473 (2)	0.2754 (3)	0.3471 (3)	0.0521 (6)
C6	−0.1908 (2)	0.1292 (4)	0.2642 (4)	0.0657 (7)
H6	−0.2661	0.1256	0.2173	0.079*
C7	−0.1260 (3)	−0.0057 (4)	0.2513 (4)	0.0753 (9)
H7	−0.1567	−0.1010	0.1967	0.090*
C8	−0.0125 (3)	−0.0015 (4)	0.3204 (4)	0.0697 (8)
H8	0.0325	−0.0934	0.3084	0.084*
C9	0.0335 (2)	0.1362 (3)	0.4058 (4)	0.0563 (7)
H9	0.1088	0.1355	0.4528	0.068*
C10	−0.0321 (2)	0.2793 (3)	0.4233 (3)	0.0469 (6)
C11	0.1246 (2)	0.4368 (3)	0.6114 (3)	0.0526 (6)
O12	0.16532 (16)	0.3125 (2)	0.6876 (3)	0.0740 (6)
C13	0.1853 (2)	0.5973 (3)	0.6331 (3)	0.0562 (7)
H13	0.1563	0.6890	0.5698	0.067*
C14	0.2804 (2)	0.6132 (3)	0.7411 (4)	0.0581 (7)
H14	0.3076	0.5175	0.7989	0.070*
C15	0.3469 (2)	0.7639 (4)	0.7790 (4)	0.0543 (7)
C16	0.3072 (2)	0.9202 (3)	0.7270 (4)	0.0637 (8)
H16	0.2357	0.9297	0.6651	0.076*
C17	0.3705 (2)	1.0620 (4)	0.7642 (4)	0.0682 (9)
H17	0.3421	1.1656	0.7282	0.082*
C18	0.4770 (2)	1.0472 (4)	0.8560 (4)	0.0674 (9)
C19	0.5195 (2)	0.8945 (4)	0.9109 (4)	0.0711 (8)
H19	0.5912	0.8856	0.9723	0.085*
C20	0.4540 (2)	0.7544 (4)	0.8731 (4)	0.0674 (8)
H20	0.4821	0.6514	0.9115	0.081*
Cl21	0.55687 (8)	1.22525 (11)	0.90310 (13)	0.1042 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0455 (14)	0.0522 (15)	0.0381 (14)	0.0023 (11)	0.0074 (11)	0.0011 (12)
C2	0.0602 (17)	0.0538 (15)	0.0500 (16)	0.0043 (12)	0.0113 (13)	−0.0061 (13)
C3	0.0541 (17)	0.0693 (18)	0.0619 (18)	0.0165 (13)	0.0081 (14)	−0.0018 (16)
C4	0.0477 (15)	0.085 (2)	0.0521 (16)	0.0047 (14)	0.0058 (12)	0.0001 (16)
C5	0.0527 (15)	0.0656 (17)	0.0384 (15)	−0.0037 (13)	0.0074 (12)	0.0013 (14)
C6	0.0662 (18)	0.077 (2)	0.0528 (17)	−0.0111 (17)	0.0052 (14)	−0.0025 (17)
C7	0.102 (3)	0.066 (2)	0.057 (2)	−0.0178 (18)	0.0114 (18)	−0.0110 (16)
C8	0.104 (3)	0.0555 (17)	0.0522 (17)	0.0068 (16)	0.0217 (17)	−0.0032 (15)
C9	0.0653 (18)	0.0581 (15)	0.0469 (16)	0.0059 (13)	0.0126 (13)	0.0024 (14)
C10	0.0550 (16)	0.0516 (14)	0.0364 (14)	0.0008 (12)	0.0144 (12)	0.0049 (12)
C11	0.0533 (16)	0.0559 (16)	0.0491 (16)	0.0055 (12)	0.0090 (12)	0.0026 (13)
O12	0.0674 (13)	0.0677 (12)	0.0812 (15)	0.0034 (10)	−0.0100 (11)	0.0117 (12)
C13	0.0557 (17)	0.0613 (16)	0.0510 (16)	0.0029 (12)	0.0059 (14)	0.0043 (13)
C14	0.0491 (15)	0.0708 (17)	0.0544 (17)	0.0051 (13)	0.0071 (13)	0.0069 (15)
C15	0.0413 (15)	0.073 (2)	0.0478 (16)	−0.0009 (13)	0.0049 (12)	0.0011 (13)
C16	0.0448 (16)	0.079 (2)	0.065 (2)	−0.0034 (14)	−0.0015 (13)	0.0077 (16)
C17	0.0483 (17)	0.077 (2)	0.078 (2)	−0.0085 (13)	0.0042 (15)	0.0113 (16)
C18	0.0488 (18)	0.089 (2)	0.065 (2)	−0.0120 (15)	0.0101 (15)	−0.0020 (17)
C19	0.0420 (16)	0.096 (2)	0.073 (2)	0.0000 (15)	−0.0023 (14)	−0.0061 (19)
C20	0.0532 (17)	0.080 (2)	0.066 (2)	0.0088 (14)	−0.0019 (14)	0.0034 (16)
Cl21	0.0772 (5)	0.1122 (7)	0.1174 (8)	−0.0353 (5)	−0.0068 (5)	−0.0004 (6)

Geometric parameters (Å, º) top

C1—C2	1.379 (3)	C9—H9	0.9300
C1—C10	1.438 (3)	C11—O12	1.232 (3)
C1—C11	1.491 (3)	C11—C13	1.483 (4)
C2—C3	1.404 (4)	C13—C14	1.331 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.359 (4)	C14—C15	1.462 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.410 (4)	C15—C16	1.387 (4)
C4—H4	0.9300	C15—C20	1.395 (4)
C5—C6	1.410 (4)	C16—C17	1.382 (4)
C5—C10	1.431 (3)	C16—H16	0.9300
C6—C7	1.350 (4)	C17—C18	1.385 (4)
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.398 (4)	C18—C19	1.378 (4)
C7—H7	0.9300	C18—Cl21	1.737 (3)
C8—C9	1.371 (4)	C19—C20	1.385 (4)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.415 (3)	C20—H20	0.9300

C2—C1—C10	119.2 (2)	C5—C10—C1	118.6 (2)
C2—C1—C11	118.7 (2)	O12—C11—C13	119.8 (3)
C10—C1—C11	122.0 (2)	O12—C11—C1	120.6 (2)
C1—C2—C3	121.9 (3)	C13—C11—C1	119.5 (2)
C1—C2—H2	119.1	C14—C13—C11	121.5 (3)
C3—C2—H2	119.1	C14—C13—H13	119.2
C4—C3—C2	119.4 (3)	C11—C13—H13	119.2
C4—C3—H3	120.3	C13—C14—C15	127.3 (3)
C2—C3—H3	120.3	C13—C14—H14	116.3
C3—C4—C5	122.0 (2)	C15—C14—H14	116.3
C3—C4—H4	119.0	C16—C15—C20	117.4 (3)
C5—C4—H4	119.0	C16—C15—C14	122.5 (2)
C4—C5—C6	122.1 (2)	C20—C15—C14	120.1 (3)
C4—C5—C10	118.8 (2)	C17—C16—C15	122.1 (3)
C6—C5—C10	119.1 (2)	C17—C16—H16	119.0
C7—C6—C5	121.7 (3)	C15—C16—H16	119.0
C7—C6—H6	119.1	C16—C17—C18	118.8 (3)
C5—C6—H6	119.1	C16—C17—H17	120.6
C6—C7—C8	119.7 (3)	C18—C17—H17	120.6
C6—C7—H7	120.1	C19—C18—C17	121.0 (3)
C8—C7—H7	120.1	C19—C18—Cl21	120.0 (2)
C9—C8—C7	121.0 (3)	C17—C18—Cl21	118.9 (3)
C9—C8—H8	119.5	C18—C19—C20	119.0 (3)
C7—C8—H8	119.5	C18—C19—H19	120.5
C8—C9—C10	120.9 (3)	C20—C19—H19	120.5
C8—C9—H9	119.5	C19—C20—C15	121.6 (3)
C10—C9—H9	119.5	C19—C20—H20	119.2
C9—C10—C5	117.6 (2)	C15—C20—H20	119.2
C9—C10—C1	123.7 (2)

C10—C1—C2—C3	4.0 (4)	C11—C1—C10—C5	170.1 (2)
C11—C1—C2—C3	−171.1 (2)	C2—C1—C11—O12	146.6 (3)
C1—C2—C3—C4	−0.1 (4)	C10—C1—C11—O12	−28.3 (4)
C2—C3—C4—C5	−3.1 (4)	C2—C1—C11—C13	−29.9 (3)
C3—C4—C5—C6	−175.0 (3)	C10—C1—C11—C13	155.1 (2)
C3—C4—C5—C10	2.1 (4)	O12—C11—C13—C14	−3.9 (4)
C4—C5—C6—C7	175.5 (3)	C1—C11—C13—C14	172.7 (2)
C10—C5—C6—C7	−1.6 (4)	C11—C13—C14—C15	−178.0 (3)
C5—C6—C7—C8	−0.4 (4)	C13—C14—C15—C16	11.7 (4)
C6—C7—C8—C9	1.9 (4)	C13—C14—C15—C20	−169.2 (3)
C7—C8—C9—C10	−1.3 (4)	C20—C15—C16—C17	0.6 (4)
C8—C9—C10—C5	−0.7 (3)	C14—C15—C16—C17	179.7 (3)
C8—C9—C10—C1	−177.5 (2)	C15—C16—C17—C18	0.2 (4)
C4—C5—C10—C9	−175.1 (2)	C16—C17—C18—C19	−0.4 (4)
C6—C5—C10—C9	2.1 (3)	C16—C17—C18—Cl21	−180.0 (2)
C4—C5—C10—C1	1.9 (3)	C17—C18—C19—C20	−0.1 (4)
C6—C5—C10—C1	179.1 (2)	Cl21—C18—C19—C20	179.4 (2)
C2—C1—C10—C9	171.9 (2)	C18—C19—C20—C15	0.9 (4)
C11—C1—C10—C9	−13.2 (4)	C16—C15—C20—C19	−1.2 (4)
C2—C1—C10—C5	−4.8 (3)	C14—C15—C20—C19	179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O12ⁱ	0.93	2.42	3.180 (4)	139
C3—H3···Cl21ⁱⁱ	0.93	2.92	3.703 (3)	143
C8—H8···O12ⁱⁱⁱ	0.93	2.64	3.546 (4)	163

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃ClO
M_r	292.74
Crystal system, space group	Monoclinic, Pc
Temperature (K)	295
a, b, c (Å)	12.0392 (14), 8.0544 (5), 7.8472 (6)
β (°)	98.091 (10)
V (Å³)	753.36 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.667, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	2481, 1866, 1440
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.083, 0.96
No. of reflections	1866
No. of parameters	190
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.13
Absolute structure	Flack (1983), 423 Friedel pairs
Absolute structure parameter	0.08 (7)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), Stereochemical Workstation Operation Manual (Siemens, 1989).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O12ⁱ	0.93	2.42	3.180 (4)	139.3
C3—H3···Cl21ⁱⁱ	0.93	2.92	3.703 (3)	142.6
C8—H8···O12ⁱⁱⁱ	0.93	2.64	3.546 (4)	163.3

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

Acknowledgements

SS thanks Mangalore University for the research facilitie.

References

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