2-[(E)-4-(Dimethyl-amino)-benzyl-idene]indan-1-one.

In the title compound, C(18)H(17)NO, the dihydro-indene ring system is approximately planar, with a maximum deviation of 0.041 (2) Å. This ring system is almost coplanar with the benzene ring, making a dihedral angle of 5.22 (9)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains along the b axis.

Related literature

For the background to dihydro­indene and its derivatives, see: Kohlhagen et al. (1998 ▶); Prasad et al. (2006 ▶); Tomar et al. (2007 ▶); Bhat et al. (2005 ▶); Trivedi et al. (2007 ▶); Solankee et al. (2010 ▶); Liu et al. (2003 ▶); Trivedi et al. (2008 ▶); Cheng et al. (2008 ▶). For a closely related structure, see: Ali et al. (2010 ▶).

Experimental

Crystal data

C18H17NO

M = 263.33

Orthorhombic,

a = 30.024 (5) Å

b = 5.9898 (9) Å

c = 7.6862 (11) Å

V = 1382.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 297 K

0.46 × 0.33 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.965, T max = 0.995

8530 measured reflections

2147 independent reflections

1657 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 1.08

2147 reflections

183 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102664X/wn2441sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102664X/wn2441Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102664X/wn2441Isup3.cml

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

C18H17NO	F(000) = 560
Mr = 263.33	Dx = 1.265 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2132 reflections
a = 30.024 (5) Å	θ = 2.7–23.6°
b = 5.9898 (9) Å	µ = 0.08 mm−1
c = 7.6862 (11) Å	T = 297 K
V = 1382.3 (4) Å3	Plate, yellow
Z = 4	0.46 × 0.33 × 0.06 mm

Bruker SMART APEXII DUO CCD area-detector diffractometer	2147 independent reflections
Radiation source: fine-focus sealed tube	1657 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −42→42
Tmin = 0.965, Tmax = 0.995	k = −7→8
8530 measured reflections	l = −10→10

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.062P] where P = (Fo2 + 2Fc2)/3
2147 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.12 e Å−3
1 restraint	Δρmin = −0.12 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
O1	0.33515 (5)	0.7381 (2)	0.9621 (3)	0.0591 (4)
N1	0.58774 (5)	0.0911 (3)	0.8681 (3)	0.0523 (4)
C1	0.49445 (7)	0.4669 (3)	0.9738 (3)	0.0466 (5)
H1A	0.4900	0.6005	1.0329	0.056*
C2	0.53678 (7)	0.3789 (3)	0.9663 (3)	0.0474 (5)
H2A	0.5601	0.4536	1.0207	0.057*
C3	0.54532 (6)	0.1784 (3)	0.8779 (3)	0.0409 (4)
C4	0.50852 (6)	0.0695 (3)	0.8021 (3)	0.0428 (4)
H4A	0.5127	−0.0657	0.7449	0.051*
C5	0.46634 (6)	0.1601 (3)	0.8111 (3)	0.0418 (4)
H5A	0.4428	0.0843	0.7595	0.050*
C6	0.45795 (6)	0.3632 (3)	0.8959 (2)	0.0391 (4)
C7	0.41495 (6)	0.4734 (3)	0.9089 (3)	0.0414 (4)
H7A	0.4157	0.6095	0.9671	0.050*
C8	0.37449 (6)	0.4142 (3)	0.8522 (3)	0.0405 (4)
C9	0.35932 (6)	0.2075 (3)	0.7567 (3)	0.0443 (4)
H9A	0.3664	0.0736	0.8221	0.053*
H9B	0.3731	0.1979	0.6427	0.053*
C10	0.30926 (6)	0.2391 (3)	0.7417 (3)	0.0426 (4)
C11	0.27778 (6)	0.0936 (4)	0.6759 (3)	0.0502 (5)
H11A	0.2863	−0.0435	0.6298	0.060*
C12	0.23334 (7)	0.1555 (4)	0.6796 (3)	0.0556 (5)
H12A	0.2119	0.0594	0.6343	0.067*
C13	0.22019 (7)	0.3589 (4)	0.7499 (3)	0.0572 (5)
H13A	0.1902	0.3971	0.7518	0.069*
C14	0.25135 (7)	0.5039 (3)	0.8169 (3)	0.0536 (5)
H14A	0.2427	0.6401	0.8643	0.064*
C15	0.29614 (6)	0.4420 (3)	0.8119 (3)	0.0431 (4)
C16	0.33507 (6)	0.5593 (3)	0.8853 (3)	0.0433 (4)
C17	0.62544 (7)	0.2311 (4)	0.9114 (4)	0.0648 (7)
H17A	0.6243	0.2695	1.0326	0.097*
H17B	0.6245	0.3649	0.8426	0.097*
H17C	0.6526	0.1519	0.8876	0.097*
C18	0.59698 (7)	−0.0926 (4)	0.7520 (4)	0.0626 (6)
H18A	0.5777	−0.2155	0.7792	0.094*
H18B	0.6274	−0.1382	0.7654	0.094*
H18C	0.5920	−0.0462	0.6340	0.094*

	U11	U22	U33	U12	U13	U23
O1	0.0587 (9)	0.0423 (8)	0.0762 (11)	0.0033 (6)	0.0014 (8)	−0.0079 (8)
N1	0.0402 (8)	0.0582 (10)	0.0585 (11)	0.0032 (7)	−0.0044 (8)	−0.0105 (9)
C1	0.0468 (11)	0.0445 (10)	0.0485 (11)	−0.0034 (8)	−0.0011 (9)	−0.0097 (9)
C2	0.0422 (10)	0.0517 (11)	0.0484 (11)	−0.0068 (8)	−0.0055 (9)	−0.0099 (10)
C3	0.0397 (9)	0.0456 (9)	0.0375 (9)	−0.0028 (7)	−0.0002 (8)	0.0006 (8)
C4	0.0441 (10)	0.0387 (9)	0.0457 (11)	−0.0029 (7)	−0.0001 (8)	−0.0041 (8)
C5	0.0394 (9)	0.0399 (9)	0.0462 (10)	−0.0074 (7)	−0.0027 (8)	−0.0035 (8)
C6	0.0391 (9)	0.0397 (9)	0.0384 (10)	−0.0046 (7)	0.0014 (8)	0.0010 (8)
C7	0.0459 (10)	0.0365 (9)	0.0419 (11)	−0.0027 (7)	0.0037 (8)	0.0009 (8)
C8	0.0404 (9)	0.0376 (9)	0.0437 (10)	−0.0016 (7)	0.0037 (8)	0.0023 (8)
C9	0.0388 (9)	0.0434 (9)	0.0507 (11)	−0.0009 (7)	0.0016 (8)	−0.0020 (9)
C10	0.0400 (9)	0.0463 (10)	0.0415 (10)	−0.0026 (7)	−0.0001 (8)	0.0061 (9)
C11	0.0499 (11)	0.0533 (11)	0.0474 (11)	−0.0051 (9)	−0.0020 (9)	0.0017 (10)
C12	0.0455 (11)	0.0691 (14)	0.0523 (12)	−0.0102 (10)	−0.0053 (10)	0.0080 (12)
C13	0.0401 (10)	0.0709 (14)	0.0606 (13)	0.0029 (9)	−0.0030 (10)	0.0141 (12)
C14	0.0477 (10)	0.0536 (10)	0.0597 (13)	0.0070 (9)	0.0015 (10)	0.0096 (11)
C15	0.0414 (9)	0.0437 (9)	0.0442 (10)	−0.0005 (7)	0.0016 (8)	0.0078 (9)
C16	0.0451 (10)	0.0373 (9)	0.0476 (11)	0.0003 (7)	0.0037 (9)	0.0072 (9)
C17	0.0396 (10)	0.0734 (15)	0.0815 (18)	−0.0012 (10)	−0.0097 (11)	−0.0083 (14)
C18	0.0513 (12)	0.0626 (13)	0.0738 (16)	0.0101 (10)	0.0024 (12)	−0.0112 (13)

O1—C16	1.223 (2)	C9—H9A	0.9700
N1—C3	1.379 (2)	C9—H9B	0.9700
N1—C18	1.444 (3)	C10—C11	1.382 (3)
N1—C17	1.448 (3)	C10—C15	1.387 (3)
C1—C2	1.377 (3)	C11—C12	1.385 (3)
C1—C6	1.394 (3)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.390 (3)
C2—C3	1.403 (3)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.377 (3)
C3—C4	1.409 (3)	C13—H13A	0.9300
C4—C5	1.380 (2)	C14—C15	1.396 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.403 (3)	C15—C16	1.476 (3)
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.454 (2)	C17—H17B	0.9600
C7—C8	1.339 (2)	C17—H17C	0.9600
C7—H7A	0.9300	C18—H18A	0.9600
C8—C16	1.490 (2)	C18—H18B	0.9600
C8—C9	1.510 (3)	C18—H18C	0.9600
C9—C10	1.519 (3)
C3—N1—C18	120.01 (17)	C11—C10—C15	120.07 (18)
C3—N1—C17	119.35 (17)	C11—C10—C9	128.74 (18)
C18—N1—C17	115.67 (18)	C15—C10—C9	111.15 (16)
C2—C1—C6	122.48 (19)	C10—C11—C12	118.9 (2)
C2—C1—H1A	118.8	C10—C11—H11A	120.6
C6—C1—H1A	118.8	C12—C11—H11A	120.6
C1—C2—C3	121.07 (17)	C11—C12—C13	121.1 (2)
C1—C2—H2A	119.5	C11—C12—H12A	119.5
C3—C2—H2A	119.5	C13—C12—H12A	119.5
N1—C3—C2	121.30 (16)	C14—C13—C12	120.4 (2)
N1—C3—C4	121.75 (17)	C14—C13—H13A	119.8
C2—C3—C4	116.95 (17)	C12—C13—H13A	119.8
C5—C4—C3	121.12 (18)	C13—C14—C15	118.5 (2)
C5—C4—H4A	119.4	C13—C14—H14A	120.8
C3—C4—H4A	119.4	C15—C14—H14A	120.8
C4—C5—C6	121.96 (16)	C10—C15—C14	121.14 (18)
C4—C5—H5A	119.0	C10—C15—C16	109.94 (16)
C6—C5—H5A	119.0	C14—C15—C16	128.78 (19)
C1—C6—C5	116.40 (16)	O1—C16—C15	127.09 (17)
C1—C6—C7	117.79 (17)	O1—C16—C8	126.27 (17)
C5—C6—C7	125.81 (16)	C15—C16—C8	106.62 (16)
C8—C7—C6	131.55 (17)	N1—C17—H17A	109.5
C8—C7—H7A	114.2	N1—C17—H17B	109.5
C6—C7—H7A	114.2	H17A—C17—H17B	109.5
C7—C8—C16	120.69 (17)	N1—C17—H17C	109.5
C7—C8—C9	130.51 (16)	H17A—C17—H17C	109.5
C16—C8—C9	108.78 (15)	H17B—C17—H17C	109.5
C8—C9—C10	103.47 (15)	N1—C18—H18A	109.5
C8—C9—H9A	111.1	N1—C18—H18B	109.5
C10—C9—H9A	111.1	H18A—C18—H18B	109.5
C8—C9—H9B	111.1	N1—C18—H18C	109.5
C10—C9—H9B	111.1	H18A—C18—H18C	109.5
H9A—C9—H9B	109.0	H18B—C18—H18C	109.5
C6—C1—C2—C3	0.3 (3)	C8—C9—C10—C15	2.3 (2)
C18—N1—C3—C2	−169.1 (2)	C15—C10—C11—C12	0.7 (3)
C17—N1—C3—C2	−15.2 (3)	C9—C10—C11—C12	178.2 (2)
C18—N1—C3—C4	11.7 (3)	C10—C11—C12—C13	−0.7 (3)
C17—N1—C3—C4	165.7 (2)	C11—C12—C13—C14	0.3 (4)
C1—C2—C3—N1	179.1 (2)	C12—C13—C14—C15	0.1 (3)
C1—C2—C3—C4	−1.7 (3)	C11—C10—C15—C14	−0.3 (3)
N1—C3—C4—C5	−179.24 (19)	C9—C10—C15—C14	−178.2 (2)
C2—C3—C4—C5	1.6 (3)	C11—C10—C15—C16	175.67 (19)
C3—C4—C5—C6	−0.2 (3)	C9—C10—C15—C16	−2.2 (2)
C2—C1—C6—C5	1.1 (3)	C13—C14—C15—C10	−0.1 (3)
C2—C1—C6—C7	−178.73 (19)	C13—C14—C15—C16	−175.3 (2)
C4—C5—C6—C1	−1.2 (3)	C10—C15—C16—O1	−177.3 (2)
C4—C5—C6—C7	178.63 (19)	C14—C15—C16—O1	−1.7 (4)
C1—C6—C7—C8	−178.3 (2)	C10—C15—C16—C8	1.1 (2)
C5—C6—C7—C8	1.8 (3)	C14—C15—C16—C8	176.7 (2)
C6—C7—C8—C16	179.24 (19)	C7—C8—C16—O1	0.4 (3)
C6—C7—C8—C9	1.3 (4)	C9—C8—C16—O1	178.8 (2)
C7—C8—C9—C10	176.6 (2)	C7—C8—C16—C15	−178.01 (18)
C16—C8—C9—C10	−1.5 (2)	C9—C8—C16—C15	0.4 (2)
C8—C9—C10—C11	−175.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.97	2.47	3.305 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.97	2.47	3.305 (3)	145

Symmetry code: (i) .