1-Chloro-4-(3,4-dichloro-phen-yl)-3,4-dihydro-naphthalene-2-carbaldehyde.

The title compound, C(17)H(11)Cl(3)O, was synthesized via the Vilsmeier-Haack reaction. The dihydro-naphthalene 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 dichloro-phenyl ring. The crystal structure features inter-molecular 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 = 337.61

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.149

S = 1.09

3006 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO CCD; 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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H11Cl3O	F(000) = 688
Mr = 337.61	Dx = 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

Oxford Diffraction Xcalibur diffractometer	3006 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2143 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 16.0839 pixels mm-1	θmax = 26.0°, θmin = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −13→13
Tmin = 0.546, Tmax = 1.000	l = −16→16
15902 measured reflections

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(Fo2) + (0.0885P)2] where P = (Fo2 + 2Fc2)/3
3006 reflections	(Δ/σ)max = 0.001
234 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) .