1-Chloro-4-(3,4-dichloro­phen­yl)-3,4-dihydro­naphthalene-2-carbaldehyde

Devarajegowda, H.C.; Nagendra, P.; Jeyaseelan, S.; Chidananda, N.; Poojary, B.

doi:10.1107/S160053681100105X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o378

doi:10.1107/S160053681100105X

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1-Chloro-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalene-2-carbaldehyde

H. C. Devarajegowda,^a ^* P. Nagendra,^b S. Jeyaseelan,^a N. Chidananda ^c and Boja Poojary ^c

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bDepartment of Chemistry, Bharathi College, Bharathinagar 571 422, Mandya District, Karnataka, India, and ^cDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 7 November 2010; accepted 7 January 2011; online 15 January 2011)

The title compound, C₁₇H₁₁Cl₃O, was synthesized via the Vilsmeier–Haack reaction. The dihydronaphthalene ring system is non-planar, the dihedral angle between the two fused rings being 10.87 (13)°; it forms a dihedral angle of 81.45 (10)° with the dichlorophenyl ring. The crystal structure features intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background to 4-(3,4-dichlorophenyl)-3,4- dihydronaphthalen-1(2H)-one, see: Zhengxu et al. (2007 ); Jerussi et al. (2004 ); Taber et al. (2004 ); Ray et al. (2003 ); Meth-Cohn & Stanforth (1991 ); Hurd & Webb (1941 ); Mallegol et al. (2005 ). For the synthesis, see Vilsmeier et al. (1937 ). For a related structure, see: Gowda et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₁Cl₃O
M_r = 337.61
Monoclinic, P 2₁ /c
a = 10.2969 (5) Å
b = 10.8849 (5) Å
c = 13.6144 (7) Å
β = 91.436 (5)°
V = 1525.43 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 293 K
0.22 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.546, T_max = 1.000
15902 measured reflections
3006 independent reflections
2143 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.149
S = 1.09
3006 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O4ⁱ	0.90 (3)	2.58 (3)	3.201 (3)	128 (2)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100105X/bv2168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100105X/bv2168Isup2.hkl

checkCIF report

Comment top

Recently drug candidates for blocking the monoamine reuptake trasporters have considerable interest in the pharmaceutical industry for treatment of central nervous system disorders (Zhengxu et al., 2007). 1,2,3,4-tetrahydronaphthalene derivatives are for the treatment of central nervous system disorders (Jerussi et al., 2004; Taber et al., 2004). Tetrahydronaphthalene derivatives are also used in liquid crystal display elements (Ray et al., 2003). Potent pharmaceutically active 1-chloro-4-(3,4-dichlorophenyl)-3, 4-dihydronaphthalene-2-carbaldehyde was prepared by the Vilsmeier- Haack reaction (Vilsmeier et al., 1937; Meth-Cohn et al. , 1991; Hurd et al., 1941; Mallegol et al., 2005) of 4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-one.

The asymmetric unit of the 1-chloro-4-(3,4-dichlorophenyl)-3,4- dihydronaphthalene-2-carbaldehyde contains one molecule (Fig. 1). The dihydronaphthalene ring system is non-planar; the dihedral angle between the two ring system of the naphthalene ring is 10.87 (13)° and also the dihedral angle between the dihydronaphthalene ring system and the dichlorophenyl ring is 81.45 (10)°. The crystal structure shows intramolecular C5—H5···Cl1, C9—H9···Cl1, C15—H15B···O4 and C18—H18···O4 intermolecular hydrogen bonds. Bond distances within the aromatic rings are in agreement with those observed related structures (Gowda et al., 2008). The packing of the molecules shows when viewed along the a axis (Fig.2).

Related literature top

For general background to 4-(3,4-dichlorophenyl)-3,4- dihydronaphthalen-1(2H)-one, see: Zhengxu et al. (2007); Jerussi et al. (2004); Taber et al. (2004); Ray et al. (2003); Meth-Cohn & Stanforth (1991); Hurd & Webb (1941); Mallegol et al. (2005). For the synthesis, see Vilsmeier et al. (1937). For a related structure, see: Gowda et al. (2008).

Experimental top

To the Vilsmeier-Haack complex prepared from DMF and POCl₃ (0.03 mol) at 0°C, the compound 4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-one (0.01 mol) was added and the reaction mixture was stirred at 65°C for 4 h. The reaction completion was monitored by TLC. The contents were cooled, poured in to ice-cold water and neutralized using Na₂CO₃ solution. The product that separated was filtered and dried. X-ray quality crystals were obtained from an ethyl acetate solution.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2010); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.Dashed lines indicate hydrogen bonds
	Fig. 2. A view of the structure down the axis a.

1-Chloro-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalene-2-carbaldehyde top

Crystal data top

C₁₇H₁₁Cl₃O	F(000) = 688
M_r = 337.61	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 383 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.2969 (5) Å	Cell parameters from 3006 reflections
b = 10.8849 (5) Å	θ = 2.4–26.0°
c = 13.6144 (7) Å	µ = 0.60 mm⁻¹
β = 91.436 (5)°	T = 293 K
V = 1525.43 (13) Å³	Plate, colourless
Z = 4	0.22 × 0.15 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	3006 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2143 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 16.0839 pixels mm^-1	θ_max = 26.0°, θ_min = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.546, T_max = 1.000	l = −16→16
15902 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0885P)²] where P = (F_o² + 2F_c²)/3
3006 reflections	(Δ/σ)_max = 0.001
234 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₇H₁₁Cl₃O	V = 1525.43 (13) Å³
M_r = 337.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2969 (5) Å	µ = 0.60 mm⁻¹
b = 10.8849 (5) Å	T = 293 K
c = 13.6144 (7) Å	0.22 × 0.15 × 0.12 mm
β = 91.436 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	3006 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	2143 reflections with I > 2σ(I)
T_min = 0.546, T_max = 1.000	R_int = 0.043
15902 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.52 e Å⁻³
3006 reflections	Δρ_min = −0.33 e Å⁻³
234 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01–2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

¹H NMR (CDCl₃, 400 MHz): δ, 10.33 (s, 1H, -CHO), 6.92-8.00 (m, 7H, Ar-H), 4.13 (t, 1H, –CH proton of fused cyclohexane ring, J=10.0 Hz), 2.86-3.01(m, 2H, –CH₂ proton of fused cyclohexane ring)

IR (KBr, cm^-1): 3443.28 (-CHO), 1662.34 (C=O of aldehyde), 1595.81(C=C,aromatic), 838.883 (C-Cl), 1255.43 (C-H stretch).

FAB MASS: m/z = 337, mol. formulae: C₁₇H₁₁Cl₃O).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.40177 (8)	0.17987 (7)	0.18417 (6)	0.0642 (3)
Cl2	1.03593 (8)	0.22018 (9)	−0.40674 (6)	0.0809 (3)
Cl3	1.07383 (9)	0.35613 (9)	−0.20272 (7)	0.0853 (3)
O4	0.3558 (2)	0.4375 (2)	−0.04817 (19)	0.0873 (8)
C5	0.3745 (3)	0.3618 (3)	0.0142 (3)	0.0654 (8)
C6	0.4835 (3)	0.2751 (2)	0.01503 (19)	0.0461 (6)
C7	0.5053 (2)	0.1922 (2)	0.08561 (18)	0.0410 (6)
C8	0.6168 (2)	0.1084 (2)	0.08586 (17)	0.0389 (6)
C9	0.6561 (3)	0.0405 (2)	0.16846 (19)	0.0474 (6)
C10	0.7619 (3)	−0.0361 (3)	0.1655 (2)	0.0604 (8)
C11	0.8291 (3)	−0.0479 (3)	0.0801 (2)	0.0595 (8)
C12	0.7912 (3)	0.0171 (2)	−0.0023 (2)	0.0520 (7)
C13	0.6860 (2)	0.0965 (2)	−0.00149 (17)	0.0409 (6)
C14	0.6365 (3)	0.1633 (2)	−0.09391 (19)	0.0462 (6)
C15	0.5787 (3)	0.2861 (3)	−0.0664 (2)	0.0539 (7)
C16	0.7379 (2)	0.1794 (2)	−0.17227 (19)	0.0433 (6)
C17	0.7223 (3)	0.1248 (2)	−0.26254 (19)	0.0447 (6)
C18	0.8128 (3)	0.1384 (2)	−0.3336 (2)	0.0475 (6)
C19	0.9213 (3)	0.2083 (2)	−0.31643 (19)	0.0451 (6)
C20	0.9393 (3)	0.2661 (2)	−0.2272 (2)	0.0476 (6)
C21	0.8493 (3)	0.2513 (2)	−0.1548 (2)	0.0503 (7)
H5	0.327 (3)	0.359 (3)	0.067 (2)	0.080 (11)*
H9	0.616 (3)	0.050 (2)	0.224 (2)	0.061 (8)*
H10	0.792 (3)	−0.082 (3)	0.218 (2)	0.088 (11)*
H11	0.904 (3)	−0.096 (2)	0.0799 (18)	0.050 (7)*
H12	0.836 (3)	0.009 (2)	−0.054 (2)	0.057 (8)*
H14	0.561 (2)	0.111 (2)	−0.1275 (17)	0.040 (6)*
H17	0.653 (3)	0.068 (2)	−0.2739 (18)	0.049 (7)*
H18	0.807 (3)	0.103 (2)	−0.393 (2)	0.055 (8)*
H15A	0.668 (4)	0.339 (3)	−0.040 (3)	0.101 (12)*
H15B	0.536 (3)	0.324 (2)	−0.121 (2)	0.057 (8)*
H21	0.867 (3)	0.291 (3)	−0.090 (2)	0.061 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0575 (5)	0.0748 (5)	0.0613 (5)	0.0080 (3)	0.0232 (4)	0.0094 (4)
Cl2	0.0618 (5)	0.1218 (8)	0.0600 (5)	0.0032 (5)	0.0216 (4)	0.0190 (5)
Cl3	0.0590 (5)	0.0868 (6)	0.1103 (8)	−0.0339 (4)	0.0057 (5)	−0.0100 (5)
O4	0.0824 (17)	0.0849 (16)	0.0945 (18)	0.0370 (13)	−0.0004 (14)	0.0272 (14)
C5	0.0517 (19)	0.073 (2)	0.072 (2)	0.0171 (15)	0.0058 (17)	0.0092 (18)
C6	0.0425 (14)	0.0474 (14)	0.0484 (15)	0.0052 (11)	−0.0004 (12)	0.0029 (11)
C7	0.0372 (13)	0.0438 (13)	0.0421 (13)	−0.0044 (11)	0.0042 (11)	−0.0034 (11)
C8	0.0386 (13)	0.0339 (12)	0.0442 (13)	−0.0052 (10)	0.0001 (11)	−0.0009 (10)
C9	0.0547 (17)	0.0480 (14)	0.0396 (14)	0.0000 (12)	0.0037 (13)	0.0049 (12)
C10	0.071 (2)	0.0574 (17)	0.0522 (17)	0.0116 (15)	−0.0045 (16)	0.0149 (14)
C11	0.0551 (18)	0.0571 (17)	0.0664 (19)	0.0192 (14)	0.0034 (15)	0.0116 (14)
C12	0.0526 (17)	0.0517 (15)	0.0521 (17)	0.0102 (13)	0.0116 (14)	0.0049 (13)
C13	0.0409 (13)	0.0389 (13)	0.0430 (13)	−0.0027 (10)	0.0021 (11)	0.0042 (10)
C14	0.0415 (14)	0.0513 (15)	0.0458 (14)	−0.0039 (12)	0.0028 (12)	0.0036 (12)
C15	0.0569 (18)	0.0555 (16)	0.0496 (16)	0.0149 (14)	0.0075 (14)	0.0144 (13)
C16	0.0392 (14)	0.0436 (13)	0.0472 (15)	0.0002 (11)	0.0037 (11)	0.0098 (11)
C17	0.0467 (15)	0.0380 (13)	0.0493 (15)	−0.0048 (11)	−0.0035 (12)	0.0064 (11)
C18	0.0510 (16)	0.0484 (14)	0.0430 (15)	0.0036 (12)	−0.0020 (12)	0.0014 (12)
C19	0.0425 (14)	0.0483 (14)	0.0446 (14)	0.0042 (11)	0.0053 (12)	0.0112 (12)
C20	0.0395 (14)	0.0460 (14)	0.0570 (17)	−0.0077 (11)	−0.0005 (12)	0.0046 (12)
C21	0.0529 (16)	0.0534 (15)	0.0444 (15)	−0.0016 (12)	−0.0017 (13)	−0.0031 (13)

Geometric parameters (Å, º) top

Cl1—C7	1.740 (2)	C12—C13	1.386 (3)
Cl2—C19	1.731 (2)	C12—H12	0.86 (3)
Cl3—C20	1.722 (3)	C13—C14	1.530 (3)
O4—C5	1.195 (4)	C14—C15	1.514 (4)
C5—C6	1.466 (4)	C14—C16	1.521 (3)
C5—H5	0.88 (3)	C14—H14	1.06 (2)
C6—C7	1.333 (3)	C15—H15A	1.14 (4)
C6—C15	1.503 (3)	C15—H15B	0.94 (3)
C7—C8	1.465 (3)	C16—C17	1.371 (4)
C8—C9	1.398 (3)	C16—C21	1.404 (4)
C8—C13	1.408 (3)	C17—C18	1.368 (4)
C9—C10	1.373 (4)	C17—H17	0.95 (3)
C9—H9	0.88 (3)	C18—C19	1.367 (4)
C10—C11	1.374 (4)	C18—H18	0.89 (3)
C10—H10	0.92 (3)	C19—C20	1.377 (4)
C11—C12	1.375 (4)	C20—C21	1.379 (4)
C11—H11	0.93 (3)	C21—H21	0.99 (3)

O4—C5—C6	123.9 (3)	C16—C14—C13	114.3 (2)
O4—C5—H5	121 (2)	C15—C14—H14	106.9 (12)
C6—C5—H5	115 (2)	C16—C14—H14	105.6 (12)
C7—C6—C5	123.8 (2)	C13—C14—H14	109.1 (12)
C7—C6—C15	119.0 (2)	C6—C15—C14	112.3 (2)
C5—C6—C15	117.1 (2)	C6—C15—H15A	110.4 (19)
C6—C7—C8	122.7 (2)	C14—C15—H15A	101.8 (18)
C6—C7—Cl1	120.84 (19)	C6—C15—H15B	108.2 (16)
C8—C7—Cl1	116.44 (17)	C14—C15—H15B	111.5 (16)
C9—C8—C13	119.2 (2)	H15A—C15—H15B	113 (2)
C9—C8—C7	122.8 (2)	C17—C16—C21	118.1 (2)
C13—C8—C7	117.9 (2)	C17—C16—C14	120.8 (2)
C10—C9—C8	120.8 (2)	C21—C16—C14	121.2 (2)
C10—C9—H9	119.4 (19)	C18—C17—C16	121.4 (3)
C8—C9—H9	119.7 (19)	C18—C17—H17	118.4 (15)
C9—C10—C11	119.9 (3)	C16—C17—H17	119.8 (15)
C9—C10—H10	124 (2)	C19—C18—C17	120.5 (3)
C11—C10—H10	116 (2)	C19—C18—H18	115.4 (18)
C10—C11—C12	120.2 (3)	C17—C18—H18	124.1 (18)
C10—C11—H11	119.2 (16)	C18—C19—C20	119.8 (2)
C12—C11—H11	120.4 (16)	C18—C19—Cl2	119.3 (2)
C11—C12—C13	121.3 (3)	C20—C19—Cl2	120.9 (2)
C11—C12—H12	117.9 (19)	C19—C20—C21	119.9 (2)
C13—C12—H12	120.7 (19)	C19—C20—Cl3	121.4 (2)
C12—C13—C8	118.5 (2)	C21—C20—Cl3	118.7 (2)
C12—C13—C14	122.3 (2)	C20—C21—C16	120.3 (3)
C8—C13—C14	119.1 (2)	C20—C21—H21	118.3 (17)
C15—C14—C16	110.7 (2)	C16—C21—H21	121.3 (17)
C15—C14—C13	110.0 (2)

O4—C5—C6—C7	178.8 (3)	C12—C13—C14—C16	−24.0 (3)
O4—C5—C6—C15	2.0 (5)	C8—C13—C14—C16	160.9 (2)
C5—C6—C7—C8	−178.5 (3)	C7—C6—C15—C14	34.9 (4)
C15—C6—C7—C8	−1.7 (4)	C5—C6—C15—C14	−148.1 (3)
C5—C6—C7—Cl1	0.6 (4)	C16—C14—C15—C6	−176.7 (2)
C15—C6—C7—Cl1	177.4 (2)	C13—C14—C15—C6	−49.5 (3)
C6—C7—C8—C9	165.8 (3)	C15—C14—C16—C17	−118.7 (3)
Cl1—C7—C8—C9	−13.4 (3)	C13—C14—C16—C17	116.5 (3)
C6—C7—C8—C13	−14.4 (4)	C15—C14—C16—C21	60.7 (3)
Cl1—C7—C8—C13	166.37 (17)	C13—C14—C16—C21	−64.1 (3)
C13—C8—C9—C10	0.8 (4)	C21—C16—C17—C18	0.7 (4)
C7—C8—C9—C10	−179.4 (2)	C14—C16—C17—C18	−179.9 (2)
C8—C9—C10—C11	−1.0 (5)	C16—C17—C18—C19	−0.6 (4)
C9—C10—C11—C12	0.2 (5)	C17—C18—C19—C20	−0.4 (4)
C10—C11—C12—C13	0.6 (5)	C17—C18—C19—Cl2	178.27 (19)
C11—C12—C13—C8	−0.8 (4)	C18—C19—C20—C21	1.3 (4)
C11—C12—C13—C14	−175.9 (3)	Cl2—C19—C20—C21	−177.3 (2)
C9—C8—C13—C12	0.1 (4)	C18—C19—C20—Cl3	−179.4 (2)
C7—C8—C13—C12	−179.7 (2)	Cl2—C19—C20—Cl3	1.9 (3)
C9—C8—C13—C14	175.4 (2)	C19—C20—C21—C16	−1.3 (4)
C7—C8—C13—C14	−4.4 (3)	Cl3—C20—C21—C16	179.5 (2)
C12—C13—C14—C15	−149.2 (3)	C17—C16—C21—C20	0.3 (4)
C8—C13—C14—C15	35.7 (3)	C14—C16—C21—C20	−179.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cl1	0.88 (3)	2.62 (3)	3.053 (4)	111 (2)
C9—H9···Cl1	0.88 (3)	2.66 (3)	3.039 (3)	107 (2)
C15—H15B···O4	0.94 (3)	2.46 (3)	2.841 (4)	103.8 (19)
C18—H18···O4ⁱ	0.90 (3)	2.58 (3)	3.201 (3)	128 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁Cl₃O
M_r	337.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.2969 (5), 10.8849 (5), 13.6144 (7)
β (°)	91.436 (5)
V (Å³)	1525.43 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.22 × 0.15 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)
T_min, T_max	0.546, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15902, 3006, 2143
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.149, 1.09
No. of reflections	3006
No. of parameters	234
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.33

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2010), CrysAlis PRO CCD (Oxford Diffraction, 2010), CrysAlis PRO RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O4ⁱ	0.90 (3)	2.58 (3)	3.201 (3)	128 (2)

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

Acknowledgements

The authors thank Professor T. N. Guru Row and Mr Venkatesha R. Hathwar, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help with the data collection.

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