4-(3,4-Dichloro­phen­yl)-3,4-dihydronaphthalen-1(2H)-one

Ding, H.; Wang, X.; Liu, D.-Z.; Li, A.-J.

doi:10.1107/S1600536807043231

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o128

https://doi.org/10.1107/S1600536807043231

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4-(3,4-Dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-one

Hui Ding,^a Xin Wang,^a Dong-Zhi Liu ^a and Ai-Jun Li ^a ^*

^aSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: liaj@yeah.net

(Received 24 July 2007; accepted 4 September 2007; online 6 December 2007)

The title compound, C₁₆H₁₂Cl₂O, was synthesized from 1-naphthol and 1,2-dichlorobenzene with anhydrous aluminium chloride as a cataylst. In the molecule, the two ring systems are approximately perpendicular to one other with a dihedral angle of 82.06 (4)°. There are two CH-type hydrogen bonds.

Related literature

Synthesis: Taber et al. (2004 ); Vukics et al. (2002 ); Quallich (2005 ).

Experimental

Crystal data

C₁₆H₁₂Cl₂O
M_r = 291.16
Monoclinic, P 2₁ /n
a = 10.7705 (14) Å
b = 10.7317 (14) Å
c = 12.3765 (16) Å
β = 111.359 (6)°
V = 1332.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 113 (2) K
0.22 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.903, T_max = 0.920
16212 measured reflections
3172 independent reflections
2676 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.11
3172 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1ⁱ	0.95	2.40	3.3469 (17)	172
C9—H9⋯Cl1ⁱⁱ	0.95	2.91	3.6984 (16)	142
C16—H16⋯Cl1ⁱⁱⁱ	0.95	2.91	3.7705 (15)	151
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CHEMDRAW (Cambridgesoft, 2003 ); software used to prepare material for publication: CrystalStructure (Rigaku, 2005).

Supporting information

Crystal structure: contains datablocks DS, I. DOI: https://doi.org/10.1107/S1600536807043231/fl2151sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807043231/fl2151Isup2.hkl

checkCIF report

Comment top

The title compound (I) is an intermediate for the synthesis of sertraline hydrochloride. Sertraline hydrochloride is an inhibitor of synaptosomal serotonin uptake makng it an important pharmaceutical agent for the treatment of depression and other anxiety-related disorders.

The molecular structure of the title compound is illustrated in Fig. 1. In the molecule, the angle between the two benzene ring planes is 82.06(0.04). In the molecule, the two ring systems are approximately perpendicular to one other with a dihedral angle of 82.06 (4). There are two CH type hydrogen bonds (Cl···H at 2.9Å and O..H of 2.4 Å).

Related literature top

Synthesis: Taber et al. (2004); Vukics et al. (2002); Quallich (2005).

Experimental top

To a stirred solution of 1-naphthol(21.62 g, 0.15 mol) in 1,2-dichlorobenzene(160 ml) anhydrous AlCl3(53.3 g, 0.4 mol)was added. The reaction mixture was heated to 110¡ae and stirred at this temperature for 3 h. The mixture was then cooled to room temperature and poured into ice(300 g) and concentrated hydrochloric acid(80 ml), followed by addition of CH2Cl2(300 ml). The organic layer was separated, and washed with water(300 ml). The solvents were evaporated in vacuum. To the oily residue methanol(50 ml) was added. The product was crystallized, filtered,and then washed twice with methanol(50 ml). Yield:32.0 g(73.4%). (Taber et al., 2004; Vukics et al., 2002; Quallich, 2005). Crystals suitable for X-ray analysis were white by slow evaporation of an absolute methanol and acetone solution at room temperature over 15 days.

Structure description top

Synthesis: Taber et al. (2004); Vukics et al. (2002); Quallich (2005).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CHEMDRAW (Cambridgesoft, 2003); software used to prepare material for publication: CrystalStructure (Rigaku, 2005).

Figures top

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	Fig. 2. The crystal structure of (I), viewed along a axis

4-(3,4-Dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-one top

Crystal data top

C₁₆H₁₂Cl₂O	F(000) = 600
M_r = 291.16	D_x = 1.452 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71070 Å
a = 10.7705 (14) Å	Cell parameters from 3625 reflections
b = 10.7317 (14) Å	θ = 2.6–25.0°
c = 12.3765 (16) Å	µ = 0.47 mm⁻¹
β = 111.359 (6)°	T = 113 K
V = 1332.3 (3) Å³	Prism, colorless
Z = 4	0.22 × 0.20 × 0.18 mm

Data collection top

Rigaku Saturn diffractometer	3172 independent reflections
Radiation source: rotating anode	2676 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.035
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.903, T_max = 0.920	l = −16→16
16212 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0489P)² + 0.1288P] where P = (F_o² + 2F_c²)/3
3172 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₂Cl₂O	V = 1332.3 (3) Å³
M_r = 291.16	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7705 (14) Å	µ = 0.47 mm⁻¹
b = 10.7317 (14) Å	T = 113 K
c = 12.3765 (16) Å	0.22 × 0.20 × 0.18 mm
β = 111.359 (6)°

Data collection top

Rigaku Saturn diffractometer	3172 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2676 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.920	R_int = 0.035
16212 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.11	Δρ_max = 0.44 e Å⁻³
3172 reflections	Δρ_min = −0.23 e Å⁻³
173 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
Cl1	0.43486 (4)	0.71805 (3)	0.50411 (3)	0.01997 (10)
Cl2	0.22276 (4)	0.54210 (3)	0.54838 (3)	0.02382 (11)
O1	0.47445 (10)	0.26530 (10)	−0.12559 (9)	0.0211 (2)
C1	0.45158 (13)	0.30731 (13)	−0.04246 (12)	0.0154 (3)
C2	0.53907 (14)	0.27547 (13)	0.08047 (11)	0.0180 (3)
H2A	0.6217	0.3257	0.1024	0.022*
H2B	0.5647	0.1866	0.0838	0.022*
C3	0.47278 (14)	0.29863 (13)	0.16876 (12)	0.0180 (3)
H3A	0.5383	0.2851	0.2482	0.022*
H3B	0.3985	0.2391	0.1555	0.022*
C4	0.41922 (14)	0.43295 (13)	0.15738 (11)	0.0155 (3)
H4	0.4967	0.4897	0.1693	0.019*
C5	0.32019 (13)	0.45560 (12)	0.03435 (11)	0.0150 (3)
C6	0.33808 (13)	0.39489 (12)	−0.05995 (11)	0.0148 (3)
C7	0.24896 (14)	0.41618 (13)	−0.17352 (12)	0.0177 (3)
H7	0.2617	0.3743	−0.2363	0.021*
C8	0.14277 (15)	0.49738 (15)	−0.19542 (13)	0.0223 (3)
H8	0.0826	0.5114	−0.2725	0.027*
C9	0.12560 (15)	0.55839 (15)	−0.10222 (13)	0.0234 (3)
H9	0.0531	0.6144	−0.1162	0.028*
C10	0.21314 (15)	0.53833 (14)	0.01059 (13)	0.0201 (3)
H10	0.2002	0.5815	0.0727	0.024*
C11	0.36440 (14)	0.46337 (13)	0.25172 (11)	0.0154 (3)
C12	0.41425 (13)	0.56497 (13)	0.32404 (11)	0.0153 (3)
H12	0.4787	0.6176	0.3116	0.018*
C13	0.37027 (14)	0.59043 (13)	0.41504 (11)	0.0151 (3)
C14	0.27583 (14)	0.51357 (13)	0.43366 (12)	0.0167 (3)
C15	0.22341 (14)	0.41266 (14)	0.36055 (12)	0.0187 (3)
H15	0.1581	0.3607	0.3724	0.022*
C16	0.26752 (14)	0.38851 (14)	0.26993 (12)	0.0186 (3)
H16	0.2312	0.3201	0.2196	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0274 (2)	0.01779 (18)	0.01560 (17)	−0.00214 (14)	0.00882 (14)	−0.00271 (13)
Cl2	0.0328 (2)	0.0250 (2)	0.02175 (19)	0.00121 (15)	0.01954 (16)	0.00068 (14)
O1	0.0258 (6)	0.0237 (5)	0.0172 (5)	0.0048 (4)	0.0119 (4)	−0.0016 (4)
C1	0.0169 (7)	0.0145 (7)	0.0163 (7)	−0.0020 (5)	0.0076 (6)	−0.0007 (5)
C2	0.0203 (7)	0.0187 (7)	0.0160 (7)	0.0050 (6)	0.0079 (6)	0.0009 (5)
C3	0.0217 (7)	0.0196 (7)	0.0136 (6)	0.0034 (6)	0.0074 (6)	0.0020 (5)
C4	0.0175 (7)	0.0178 (7)	0.0125 (6)	−0.0002 (5)	0.0072 (5)	−0.0010 (5)
C5	0.0166 (7)	0.0155 (7)	0.0141 (6)	−0.0021 (5)	0.0069 (5)	0.0002 (5)
C6	0.0159 (7)	0.0148 (7)	0.0144 (6)	−0.0018 (5)	0.0064 (5)	0.0004 (5)
C7	0.0190 (7)	0.0204 (7)	0.0150 (7)	−0.0016 (6)	0.0077 (6)	−0.0022 (5)
C8	0.0199 (7)	0.0300 (8)	0.0147 (7)	0.0035 (6)	0.0034 (6)	0.0018 (6)
C9	0.0213 (7)	0.0267 (8)	0.0222 (7)	0.0091 (6)	0.0079 (6)	0.0019 (6)
C10	0.0231 (7)	0.0225 (8)	0.0167 (7)	0.0040 (6)	0.0097 (6)	−0.0007 (6)
C11	0.0162 (6)	0.0178 (7)	0.0118 (6)	0.0028 (5)	0.0048 (5)	0.0005 (5)
C12	0.0162 (7)	0.0168 (7)	0.0132 (6)	0.0007 (5)	0.0058 (5)	0.0027 (5)
C13	0.0177 (7)	0.0141 (6)	0.0123 (6)	0.0020 (5)	0.0041 (5)	0.0004 (5)
C14	0.0196 (7)	0.0189 (7)	0.0142 (7)	0.0047 (6)	0.0094 (6)	0.0038 (5)
C15	0.0176 (7)	0.0197 (7)	0.0202 (7)	−0.0017 (6)	0.0084 (6)	0.0020 (6)
C16	0.0184 (7)	0.0204 (7)	0.0162 (7)	−0.0018 (6)	0.0055 (6)	−0.0024 (6)

Geometric parameters (Å, º) top

Cl1—C13	1.7367 (14)	C7—C8	1.384 (2)
Cl2—C14	1.7400 (14)	C7—H7	0.9500
O1—C1	1.2276 (16)	C8—C9	1.396 (2)
C1—C6	1.4939 (19)	C8—H8	0.9500
C1—C2	1.5083 (19)	C9—C10	1.388 (2)
C2—C3	1.5278 (18)	C9—H9	0.9500
C2—H2A	0.9900	C10—H10	0.9500
C2—H2B	0.9900	C11—C12	1.3886 (19)
C3—C4	1.5399 (19)	C11—C16	1.399 (2)
C3—H3A	0.9900	C12—C13	1.3985 (18)
C3—H3B	0.9900	C12—H12	0.9500
C4—C11	1.5234 (18)	C13—C14	1.392 (2)
C4—C5	1.5272 (18)	C14—C15	1.392 (2)
C4—H4	1.0000	C15—C16	1.3924 (19)
C5—C10	1.399 (2)	C15—H15	0.9500
C5—C6	1.4098 (18)	C16—H16	0.9500
C6—C7	1.4024 (19)

O1—C1—C6	120.86 (12)	C6—C7—H7	119.5
O1—C1—C2	121.32 (12)	C7—C8—C9	118.83 (13)
C6—C1—C2	117.79 (11)	C7—C8—H8	120.6
C1—C2—C3	113.68 (11)	C9—C8—H8	120.6
C1—C2—H2A	108.8	C10—C9—C8	120.84 (14)
C3—C2—H2A	108.8	C10—C9—H9	119.6
C1—C2—H2B	108.8	C8—C9—H9	119.6
C3—C2—H2B	108.8	C9—C10—C5	121.05 (13)
H2A—C2—H2B	107.7	C9—C10—H10	119.5
C2—C3—C4	110.11 (11)	C5—C10—H10	119.5
C2—C3—H3A	109.6	C12—C11—C16	118.89 (12)
C4—C3—H3A	109.6	C12—C11—C4	119.70 (12)
C2—C3—H3B	109.6	C16—C11—C4	121.37 (12)
C4—C3—H3B	109.6	C11—C12—C13	120.51 (13)
H3A—C3—H3B	108.2	C11—C12—H12	119.7
C11—C4—C5	113.90 (11)	C13—C12—H12	119.7
C11—C4—C3	111.55 (11)	C14—C13—C12	119.97 (13)
C5—C4—C3	110.03 (11)	C14—C13—Cl1	120.66 (11)
C11—C4—H4	107.0	C12—C13—Cl1	119.36 (11)
C5—C4—H4	107.0	C15—C14—C13	120.07 (13)
C3—C4—H4	107.0	C15—C14—Cl2	119.42 (11)
C10—C5—C6	118.03 (12)	C13—C14—Cl2	120.51 (11)
C10—C5—C4	122.23 (12)	C14—C15—C16	119.45 (13)
C6—C5—C4	119.70 (12)	C14—C15—H15	120.3
C7—C6—C5	120.29 (12)	C16—C15—H15	120.3
C7—C6—C1	118.23 (12)	C15—C16—C11	121.08 (13)
C5—C6—C1	121.48 (12)	C15—C16—H16	119.5
C8—C7—C6	120.93 (13)	C11—C16—H16	119.5
C8—C7—H7	119.5

O1—C1—C2—C3	−160.86 (13)	C8—C9—C10—C5	−0.6 (2)
C6—C1—C2—C3	20.89 (17)	C6—C5—C10—C9	1.2 (2)
C1—C2—C3—C4	−52.96 (16)	C4—C5—C10—C9	179.15 (14)
C2—C3—C4—C11	−174.50 (11)	C5—C4—C11—C12	−110.85 (14)
C2—C3—C4—C5	58.08 (15)	C3—C4—C11—C12	123.85 (14)
C11—C4—C5—C10	23.18 (19)	C5—C4—C11—C16	71.33 (17)
C3—C4—C5—C10	149.28 (13)	C3—C4—C11—C16	−53.97 (17)
C11—C4—C5—C6	−158.88 (12)	C16—C11—C12—C13	1.3 (2)
C3—C4—C5—C6	−32.78 (16)	C4—C11—C12—C13	−176.57 (12)
C10—C5—C6—C7	−1.1 (2)	C11—C12—C13—C14	0.0 (2)
C4—C5—C6—C7	−179.11 (12)	C11—C12—C13—Cl1	179.87 (11)
C10—C5—C6—C1	178.62 (13)	C12—C13—C14—C15	−1.1 (2)
C4—C5—C6—C1	0.60 (19)	Cl1—C13—C14—C15	179.05 (11)
O1—C1—C6—C7	7.5 (2)	C12—C13—C14—Cl2	178.62 (10)
C2—C1—C6—C7	−174.23 (12)	Cl1—C13—C14—Cl2	−1.21 (17)
O1—C1—C6—C5	−172.20 (13)	C13—C14—C15—C16	0.8 (2)
C2—C1—C6—C5	6.05 (19)	Cl2—C14—C15—C16	−178.90 (11)
C5—C6—C7—C8	0.5 (2)	C14—C15—C16—C11	0.5 (2)
C1—C6—C7—C8	−179.25 (13)	C12—C11—C16—C15	−1.6 (2)
C6—C7—C8—C9	0.1 (2)	C4—C11—C16—C15	176.25 (13)
C7—C8—C9—C10	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.95	2.40	3.3469 (17)	172
C9—H9···Cl1ⁱⁱ	0.95	2.91	3.6984 (16)	142
C16—H16···Cl1ⁱⁱⁱ	0.95	2.91	3.7705 (15)	151

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂Cl₂O
M_r	291.16
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	10.7705 (14), 10.7317 (14), 12.3765 (16)
β (°)	111.359 (6)
V (Å³)	1332.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.903, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections	16212, 3172, 2676
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.11
No. of reflections	3172
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.23

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CHEMDRAW (Cambridgesoft, 2003), CrystalStructure (Rigaku, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.95	2.40	3.3469 (17)	172.0
C9—H9···Cl1ⁱⁱ	0.95	2.91	3.6984 (16)	141.5
C16—H16···Cl1ⁱⁱⁱ	0.95	2.91	3.7705 (15)	151.4

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the National Science Foundation of China (No. 20576094)

References

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