Crystal structure of (E)-2-(4-chloro­benzyl­idene)-3,4-di­hydro­naphthalen-1(2H)-one: a second monoclinic polymorph

Haroon, M.; Akhtar, T.; Tahir, M.N.

doi:10.1107/S2056989015016151

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o741-o742

doi:10.1107/S2056989015016151

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Crystal structure of (E)-2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one: a second monoclinic polymorph

Muhammad Haroon,^a Tashfeen Akhtar ^a and Muhammad Nawaz Tahir ^b ^*

^aDepartment of Chemistry, Mirpur University of Science and Technology (MUST), Mirpur, Azad Jammu and Kashmir, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 21 August 2015; accepted 28 August 2015; online 12 September 2015)

The title compound, C₁₇H₁₃ClO, is the second monoclinic polymorph to crystallize in the space group P2₁/c. The first polymorph crystallized with two independent molecules in the asymmetric unit [Bolognesi et al. (1975 ). Acta Cryst. A31, S119; Z′ = 2; no atomic coordinates available], whereas the title compound has Z′ = 1. In the title polymorph, the dihedral angle between the plane of the benzene ring of the tetralone moiety and that of the 4-chlorobenzyl ring is 52.21 (11)°. The cyclohex-2-en-1-one ring of the tetralone moiety has a screw-boat conformation. In the crystal, molecules are liked by pairs of C—H⋯π interactions forming inversion dimers. There are no other significant intermolecular interactions present.

Keywords: crystal structure; α-tetralone; C—H⋯π interactions.

CCDC reference: 1421217

1. Related literature

For a brief description of the first monoclinic polymorph of the title compound, see: Bolognesi et al. (1975). For the crystal structures of related compounds, see: Asiri et al. (2012 ); Dimmock et al. (2002 ); Oloo et al. (2002 ). For the synthesis, see: Kerbal et al. (1988 ).

2. Experimental

2.1. Crystal data

C₁₇H₁₃ClO
M_r = 268.72
Monoclinic, P 2₁ /c
a = 13.3791 (8) Å
b = 14.9352 (10) Å
c = 6.7849 (3) Å
β = 93.968 (3)°
V = 1352.51 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.38 × 0.30 × 0.26 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.906, T_max = 0.930
11640 measured reflections
2954 independent reflections
1901 reflections with I > 2σ(I)
R_int = 0.029

2.3. Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.170
S = 1.05
2954 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cg1ⁱ	0.93	2.86	3.552 (2)	132
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.

Supporting information

CCDC reference: 1421217

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015016151/su5197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016151/su5197Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015016151/su5197Isup3.cml

checkCIF report

Comments top

The crystal structure of 2-(p-chlorobenzylidene)-tetral-1-one (Bolognesi et al., 1975) is the first monoclinic polymorph of the title compound, however no atomic coordinates were reported. The crystal structures of the related structures 2-(2,4-dichlorophenylmethylene)-1- tetralone (Oloo et al., 2002), 2-[(E)-4-methoxybenzylidene]-1,2,3,4-tetrahydronaphthalen-1-one (Asiri et al., 2012), and 2-(3,4-dichlorophenylmethylene)-1-tetralone (Dimmock et al., 2002) have been published.

The molecular structure of the title polymorph is illustrated in Fig. 1. The benzene ring (C2–C7) of tetralone (systematic name: 3,4-dihydronaphthalen-1(2H)-one) and the mean plane of part of the 4-chlorobenzylidene (C11–C17/Cl1) moiety are inclined to one another by 52.03 (6)°. The cyclohex-2-en-1-one ring, (C1/C2/C7–C10), has puckering amplitude (Q) = 0.471 (2) Å, and θ = 65.6 (2)° and φ = 210.5 (3)°, and can be described as having a screw-boat conformation.

In the crystal, molecules are liked by pairs of C—H···π interactions forming inversion dimers (Table 1). There are no other significant intermolecular interactions present.

Synthesis and crystallization top

The synthesis of the title compound was carried out following a published procedure (Kerbal et al., 1988), viz. by a condensation of equimolar amounts of 4-chlorobenzaldehyde and α-tetralone using sodium hydroxide in methanol (yield; 87%; m.p.: 426–428 K). The synthesized compound was crystallized in tetrahydrofuran under slow evaporation yielding light-orange prismatic crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H-atoms were positioned geometrically (C–H = 0.93–0.97 Å) and refined as riding with U_iso(H) = 1.2U_eq(C).

Related literature top

For a brief description of the first monoclinic polymorph of the title compound, see: Bolognesi et al. (1975). For the crystal structures of related compounds, see: Asiri et al. (2012); Dimmock et al. (2002); Oloo et al. (2002). For the synthesis, see: Kerbal et al. (1988).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

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

Crystal data top

C₁₇H₁₃ClO	F(000) = 560
M_r = 268.72	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.3791 (8) Å	Cell parameters from 1901 reflections
b = 14.9352 (10) Å	θ = 2.7–27.0°
c = 6.7849 (3) Å	µ = 0.27 mm⁻¹
β = 93.968 (3)°	T = 296 K
V = 1352.51 (14) Å³	Prism, light orange
Z = 4	0.38 × 0.30 × 0.26 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2954 independent reflections
Radiation source: fine-focus sealed tube	1901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 7.70 pixels mm^-1	θ_max = 27.0°, θ_min = 2.7°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −19→18
T_min = 0.906, T_max = 0.930	l = −8→8
11640 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0931P)² + 0.1261P] where P = (F_o² + 2F_c²)/3
2954 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₃ClO	V = 1352.51 (14) Å³
M_r = 268.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3791 (8) Å	µ = 0.27 mm⁻¹
b = 14.9352 (10) Å	T = 296 K
c = 6.7849 (3) Å	0.38 × 0.30 × 0.26 mm
β = 93.968 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2954 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1901 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.930	R_int = 0.029
11640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.05	Δρ_max = 0.37 e Å⁻³
2954 reflections	Δρ_min = −0.18 e Å⁻³
172 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	−0.45111 (6)	0.12595 (6)	0.64763 (13)	0.1115 (4)
O1	0.01032 (15)	0.14379 (12)	−0.1910 (2)	0.0905 (6)
C1	0.04921 (18)	0.13078 (12)	−0.0242 (3)	0.0592 (5)
C2	0.15886 (18)	0.13063 (12)	0.0132 (3)	0.0594 (5)
C3	0.2190 (2)	0.16509 (15)	−0.1286 (4)	0.0758 (7)
H3	0.1893	0.1867	−0.2471	0.091*
C4	0.3206 (2)	0.16757 (17)	−0.0960 (5)	0.0903 (8)
H4	0.3597	0.1910	−0.1918	0.108*
C5	0.3657 (2)	0.13533 (18)	0.0791 (5)	0.0947 (9)
H5	0.4350	0.1373	0.1021	0.114*
C6	0.3064 (2)	0.09969 (16)	0.2216 (4)	0.0767 (7)
H6	0.3369	0.0774	0.3389	0.092*
C7	0.20322 (18)	0.09703 (13)	0.1913 (3)	0.0597 (5)
C8	0.13788 (16)	0.05948 (14)	0.3412 (3)	0.0638 (6)
H8A	0.1739	0.0605	0.4703	0.077*
H8B	0.1220	−0.0024	0.3086	0.077*
C9	0.04115 (17)	0.11253 (13)	0.3489 (3)	0.0588 (5)
H9A	−0.0018	0.0835	0.4390	0.071*
H9B	0.0564	0.1721	0.3992	0.071*
C10	−0.01328 (17)	0.11966 (12)	0.1487 (3)	0.0550 (5)
C11	−0.11281 (18)	0.11818 (12)	0.1126 (3)	0.0599 (6)
H11	−0.1350	0.1175	−0.0203	0.072*
C12	−0.19169 (17)	0.11744 (12)	0.2505 (3)	0.0572 (5)
C13	−0.28306 (18)	0.07683 (15)	0.1952 (3)	0.0736 (6)
H13	−0.2913	0.0487	0.0729	0.088*
C14	−0.36166 (18)	0.07709 (18)	0.3162 (4)	0.0859 (8)
H14	−0.4212	0.0477	0.2782	0.103*
C15	−0.3506 (2)	0.12143 (16)	0.4938 (4)	0.0779 (7)
C16	−0.26219 (17)	0.16368 (14)	0.5526 (3)	0.0689 (6)
H16	−0.2559	0.1942	0.6723	0.083*
C17	−0.18321 (17)	0.16064 (13)	0.4338 (3)	0.0614 (5)
H17	−0.1229	0.1878	0.4760	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0757 (5)	0.1284 (7)	0.1334 (8)	0.0051 (4)	0.0296 (5)	−0.0236 (5)
O1	0.1112 (14)	0.1190 (15)	0.0393 (8)	−0.0036 (11)	−0.0092 (8)	0.0101 (8)
C1	0.0875 (16)	0.0509 (11)	0.0383 (10)	−0.0005 (10)	−0.0030 (9)	0.0017 (8)
C2	0.0872 (15)	0.0442 (10)	0.0469 (10)	0.0026 (9)	0.0066 (10)	0.0004 (8)
C3	0.103 (2)	0.0587 (13)	0.0674 (14)	0.0112 (12)	0.0194 (13)	0.0091 (10)
C4	0.103 (2)	0.0666 (15)	0.105 (2)	0.0074 (14)	0.0359 (16)	0.0120 (14)
C5	0.0834 (19)	0.0756 (17)	0.126 (3)	0.0051 (14)	0.0139 (18)	−0.0056 (16)
C6	0.0839 (18)	0.0650 (14)	0.0801 (16)	0.0072 (12)	−0.0013 (13)	−0.0022 (12)
C7	0.0798 (15)	0.0456 (10)	0.0529 (11)	0.0036 (9)	−0.0008 (10)	−0.0052 (8)
C8	0.0849 (15)	0.0601 (12)	0.0446 (10)	0.0039 (10)	−0.0093 (9)	0.0068 (9)
C9	0.0785 (14)	0.0581 (11)	0.0387 (9)	−0.0024 (10)	−0.0037 (9)	0.0037 (8)
C10	0.0790 (15)	0.0441 (10)	0.0404 (10)	−0.0013 (9)	−0.0070 (9)	0.0016 (7)
C11	0.0843 (16)	0.0474 (11)	0.0453 (10)	0.0016 (9)	−0.0137 (10)	−0.0023 (8)
C12	0.0691 (13)	0.0440 (10)	0.0563 (11)	0.0052 (8)	−0.0109 (9)	−0.0017 (8)
C13	0.0747 (15)	0.0690 (14)	0.0740 (14)	0.0063 (12)	−0.0172 (12)	−0.0173 (11)
C14	0.0631 (15)	0.0827 (17)	0.109 (2)	0.0007 (12)	−0.0133 (14)	−0.0218 (15)
C15	0.0698 (16)	0.0701 (15)	0.0940 (18)	0.0099 (11)	0.0064 (13)	−0.0040 (13)
C16	0.0787 (16)	0.0575 (12)	0.0696 (13)	0.0069 (11)	−0.0009 (11)	−0.0084 (10)
C17	0.0744 (14)	0.0477 (11)	0.0607 (12)	−0.0011 (9)	−0.0068 (10)	−0.0051 (9)

Geometric parameters (Å, º) top

Cl1—C15	1.759 (3)	C8—H8B	0.9700
O1—C1	1.227 (2)	C9—C10	1.500 (3)
C1—C2	1.471 (3)	C9—H9A	0.9700
C1—C10	1.496 (3)	C9—H9B	0.9700
C2—C3	1.394 (3)	C10—C11	1.337 (3)
C2—C7	1.402 (3)	C11—C12	1.458 (3)
C3—C4	1.363 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.393 (3)
C4—C5	1.382 (4)	C12—C17	1.399 (3)
C4—H4	0.9300	C13—C14	1.378 (3)
C5—C6	1.398 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.374 (4)
C6—C7	1.383 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—C16	1.376 (3)
C7—C8	1.495 (3)	C16—C17	1.373 (3)
C8—C9	1.521 (3)	C16—H16	0.9300
C8—H8A	0.9700	C17—H17	0.9300

O1—C1—C2	120.87 (19)	C8—C9—H9A	109.3
O1—C1—C10	121.1 (2)	C10—C9—H9B	109.3
C2—C1—C10	117.97 (16)	C8—C9—H9B	109.3
C3—C2—C7	119.8 (2)	H9A—C9—H9B	108.0
C3—C2—C1	119.8 (2)	C11—C10—C1	117.49 (17)
C7—C2—C1	120.46 (18)	C11—C10—C9	125.41 (19)
C4—C3—C2	121.0 (2)	C1—C10—C9	117.09 (19)
C4—C3—H3	119.5	C10—C11—C12	129.69 (18)
C2—C3—H3	119.5	C10—C11—H11	115.2
C3—C4—C5	120.1 (3)	C12—C11—H11	115.2
C3—C4—H4	120.0	C13—C12—C17	117.1 (2)
C5—C4—H4	120.0	C13—C12—C11	119.44 (18)
C4—C5—C6	119.5 (3)	C17—C12—C11	123.31 (19)
C4—C5—H5	120.2	C14—C13—C12	122.0 (2)
C6—C5—H5	120.2	C14—C13—H13	119.0
C7—C6—C5	121.1 (2)	C12—C13—H13	119.0
C7—C6—H6	119.4	C15—C14—C13	119.0 (2)
C5—C6—H6	119.4	C15—C14—H14	120.5
C6—C7—C2	118.5 (2)	C13—C14—H14	120.5
C6—C7—C8	122.29 (19)	C14—C15—C16	120.9 (2)
C2—C7—C8	119.2 (2)	C14—C15—Cl1	119.9 (2)
C7—C8—C9	111.51 (16)	C16—C15—Cl1	119.2 (2)
C7—C8—H8A	109.3	C17—C16—C15	119.8 (2)
C9—C8—H8A	109.3	C17—C16—H16	120.1
C7—C8—H8B	109.3	C15—C16—H16	120.1
C9—C8—H8B	109.3	C16—C17—C12	121.2 (2)
H8A—C8—H8B	108.0	C16—C17—H17	119.4
C10—C9—C8	111.52 (17)	C12—C17—H17	119.4
C10—C9—H9A	109.3

O1—C1—C2—C3	14.6 (3)	C2—C1—C10—C11	−178.76 (17)
C10—C1—C2—C3	−162.05 (18)	O1—C1—C10—C9	−174.51 (19)
O1—C1—C2—C7	−166.10 (19)	C2—C1—C10—C9	2.2 (2)
C10—C1—C2—C7	17.2 (3)	C8—C9—C10—C11	143.7 (2)
C7—C2—C3—C4	−0.7 (3)	C8—C9—C10—C1	−37.3 (2)
C1—C2—C3—C4	178.6 (2)	C1—C10—C11—C12	−173.08 (18)
C2—C3—C4—C5	0.3 (4)	C9—C10—C11—C12	5.9 (3)
C3—C4—C5—C6	0.4 (4)	C10—C11—C12—C13	−151.1 (2)
C4—C5—C6—C7	−0.7 (4)	C10—C11—C12—C17	33.0 (3)
C5—C6—C7—C2	0.3 (3)	C17—C12—C13—C14	−1.3 (3)
C5—C6—C7—C8	−179.9 (2)	C11—C12—C13—C14	−177.4 (2)
C3—C2—C7—C6	0.4 (3)	C12—C13—C14—C15	2.3 (4)
C1—C2—C7—C6	−178.84 (19)	C13—C14—C15—C16	−1.1 (4)
C3—C2—C7—C8	−179.42 (18)	C13—C14—C15—Cl1	177.9 (2)
C1—C2—C7—C8	1.3 (3)	C14—C15—C16—C17	−0.9 (4)
C6—C7—C8—C9	142.9 (2)	Cl1—C15—C16—C17	180.00 (17)
C2—C7—C8—C9	−37.3 (3)	C15—C16—C17—C12	1.9 (3)
C7—C8—C9—C10	54.1 (2)	C13—C12—C17—C16	−0.8 (3)
O1—C1—C10—C11	4.6 (3)	C11—C12—C17—C16	175.17 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg1ⁱ	0.93	2.86	3.552 (2)	132

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg1ⁱ	0.93	2.86	3.552 (2)	132

Symmetry code: (i) −x, −y, −z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o741-o742

doi:10.1107/S2056989015016151

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (E)-2-(4-chloro­benzyl­­idene)-3,4-di­hydro­naphthalen-1(2H)-one: a second monoclinic polymorph

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one: a second monoclinic polymorph