Crystal structure of (E)-2-(4-chloro-benzyl-idene)-3,4-di-hydro-naphthalen-1(2H)-one: a second monoclinic polymorph.

The title compound, C17H13ClO, is the second monoclinic polymorph to crystallize in the space group P21/c. The first polymorph crystallized with two independent mol-ecules 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 tetra-lone moiety and that of the 4-chloro-benzyl ring is 52.21 (11)°. The cyclo-hex-2-en-1-one ring of the tetra-lone moiety has a screw-boat conformation. In the crystal, mol-ecules are liked by pairs of C-H⋯π inter-actions forming inversion dimers. There are no other significant inter-molecular inter-actions present.

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 ▸).

Experimental

Crystal data

C17H13ClO

M = 268.72

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.170

S = 1.05

2954 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.19 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015016151/su5197sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S2056989015016151/su5197fig1.tif

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

CCDC reference: 1421217

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H13ClO	F(000) = 560
Mr = 268.72	Dx = 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

Bruker Kappa APEXII CCD diffractometer	2954 independent reflections
Radiation source: fine-focus sealed tube	1901 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 7.70 pixels mm-1	θmax = 27.0°, θmin = 2.7°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −19→18
Tmin = 0.906, Tmax = 0.930	l = −8→8
11640 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0931P)2 + 0.1261P] where P = (Fo2 + 2Fc2)/3
2954 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C2C7 ring.

DHA	DH	HA	D A	DHA
C13H13Cg1i	0.93	2.86	3.552(2)	132

Symmetry code: (i) .