1-(4-{2-[(E)-3-(4-Chloro-phen-yl)-3-oxo-prop-1-en-1-yl]phen-oxy}but-yl)-1H-indole-3-carbaldehyde.

In the title compound, C(28)H(24)ClNO(3), the dihedral angles between the central benzene ring and the indole ring system and the chlorobenzene ring are 70.81 (5) and 78.62 (5)°, respectively. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O inter-action. In the crystal, pairs of C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers with an R(2) (2)(14) motif.

Related literature

For the biological activity of indole derivatives, see: Olgen & Coban (2003 ▶); Ho et al. (1986 ▶); Joshi & Chand (1982 ▶); Rodriguez et al. (1985 ▶); Okabe & Adachi (1998 ▶); Merck (1973 ▶). For N-atom hybridization, see: Beddoes et al. (1986 ▶). For a related structure, see: Paramasivam et al. (2012 ▶). For graph-set notation see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H24ClNO3

M = 457.93

Monoclinic,

a = 8.7126 (3) Å

b = 19.1311 (6) Å

c = 13.9338 (4) Å

β = 93.198 (2)°

V = 2318.89 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

22253 measured reflections

5782 independent reflections

4060 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.145

S = 1.03

5782 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windowa (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002456/kp2444sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002456/kp2444Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002456/kp2444Isup3.cml

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

C28H24ClNO3	F(000) = 960
Mr = 457.93	monoclinic
Monoclinic, P21/n	Dx = 1.312 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.7126 (3) Å	Cell parameters from 5782 reflections
b = 19.1311 (6) Å	θ = 1.8–28.3°
c = 13.9338 (4) Å	µ = 0.20 mm−1
β = 93.198 (2)°	T = 298 K
V = 2318.89 (13) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.20 mm

Bruker SMART APEXII area-detector diffractometer	4060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 28.3°, θmin = 1.8°
ω and φ scans	h = −8→11
22253 measured reflections	k = −25→21
5782 independent reflections	l = −18→18

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.7822P] where P = (Fo2 + 2Fc2)/3
5782 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.46 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
C1	−0.0037 (3)	0.70610 (12)	0.90463 (15)	0.0675 (5)
C2	0.0110 (3)	0.63646 (12)	0.88447 (16)	0.0743 (6)
H2	−0.0351	0.6177	0.8284	0.089*
C3	0.0951 (3)	0.59454 (11)	0.94836 (14)	0.0656 (5)
H3	0.1071	0.5474	0.9341	0.079*
C4	0.1623 (2)	0.62099 (10)	1.03343 (13)	0.0526 (4)
C5	0.1383 (3)	0.69100 (11)	1.05371 (16)	0.0700 (6)
H5	0.1781	0.7095	1.1116	0.084*
C6	0.0566 (3)	0.73364 (12)	0.98970 (18)	0.0776 (7)
H6	0.0423	0.7806	1.0039	0.093*
C7	0.2526 (2)	0.57743 (10)	1.10492 (13)	0.0559 (4)
C8	0.3047 (2)	0.50761 (10)	1.07578 (13)	0.0552 (4)
H8	0.2842	0.4926	1.0129	0.066*
C9	0.3803 (2)	0.46590 (9)	1.13797 (12)	0.0488 (4)
H9	0.3943	0.4842	1.1997	0.059*
C10	0.44511 (19)	0.39676 (9)	1.12663 (11)	0.0450 (4)
C11	0.5351 (2)	0.36906 (10)	1.20364 (12)	0.0535 (4)
H11	0.5511	0.3958	1.2590	0.064*
C12	0.6008 (3)	0.30409 (11)	1.20085 (14)	0.0647 (5)
H12	0.6605	0.2874	1.2533	0.078*
C13	0.5775 (3)	0.26396 (11)	1.11985 (15)	0.0688 (6)
H13	0.6221	0.2199	1.1174	0.083*
C14	0.4884 (3)	0.28835 (10)	1.04196 (13)	0.0609 (5)
H14	0.4723	0.2604	0.9878	0.073*
C15	0.4230 (2)	0.35419 (9)	1.04394 (11)	0.0472 (4)
C16	0.2994 (3)	0.33837 (10)	0.88721 (13)	0.0632 (5)
H16A	0.2491	0.2958	0.9063	0.076*
H16B	0.3921	0.3260	0.8558	0.076*
C17	0.1931 (3)	0.38074 (11)	0.82024 (13)	0.0612 (5)
H17A	0.1520	0.3506	0.7690	0.073*
H17B	0.1074	0.3973	0.8556	0.073*
C18	0.2704 (2)	0.44254 (11)	0.77648 (12)	0.0571 (5)
H18A	0.3509	0.4258	0.7370	0.068*
H18B	0.3183	0.4708	0.8276	0.068*
C19	0.1603 (2)	0.48804 (10)	0.71534 (12)	0.0583 (5)
H19A	0.0824	0.5064	0.7556	0.070*
H19B	0.2167	0.5274	0.6911	0.070*
C20	−0.0653 (2)	0.43252 (9)	0.62598 (12)	0.0485 (4)
H20	−0.1354	0.4400	0.6729	0.058*
C21	−0.09949 (19)	0.40123 (9)	0.53853 (11)	0.0445 (4)
C22	−0.2501 (2)	0.37870 (11)	0.50518 (14)	0.0564 (5)
H22	−0.3284	0.3832	0.5475	0.068*
C23	0.04045 (18)	0.39990 (8)	0.48909 (11)	0.0404 (3)
C24	0.15337 (18)	0.43141 (8)	0.55073 (11)	0.0420 (3)
C25	0.3043 (2)	0.43976 (10)	0.52522 (13)	0.0526 (4)
H25	0.3779	0.4609	0.5665	0.063*
C26	0.3401 (2)	0.41551 (11)	0.43653 (14)	0.0596 (5)
H26	0.4400	0.4207	0.4172	0.071*
C27	0.2308 (2)	0.38327 (11)	0.37477 (13)	0.0583 (5)
H27	0.2594	0.3668	0.3155	0.070*
C28	0.0807 (2)	0.37520 (10)	0.39963 (11)	0.0492 (4)
H28	0.0082	0.3538	0.3578	0.059*
N1	0.08465 (17)	0.45088 (7)	0.63409 (9)	0.0469 (3)
O1	0.2827 (2)	0.59973 (9)	1.18603 (10)	0.0837 (5)
O2	0.33578 (16)	0.38163 (6)	0.96938 (8)	0.0570 (3)
O3	−0.28421 (16)	0.35426 (9)	0.42671 (11)	0.0757 (4)
Cl1	−0.10168 (10)	0.76018 (4)	0.82139 (5)	0.1058 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0800 (14)	0.0584 (12)	0.0639 (12)	0.0172 (11)	0.0030 (10)	−0.0019 (10)
C2	0.0966 (17)	0.0648 (14)	0.0599 (12)	0.0149 (12)	−0.0089 (11)	−0.0127 (10)
C3	0.0897 (15)	0.0488 (11)	0.0576 (11)	0.0095 (10)	−0.0022 (10)	−0.0117 (9)
C4	0.0585 (10)	0.0466 (10)	0.0532 (9)	0.0020 (8)	0.0097 (8)	−0.0081 (8)
C5	0.0835 (15)	0.0548 (12)	0.0704 (13)	0.0083 (11)	−0.0079 (11)	−0.0187 (10)
C6	0.0954 (17)	0.0479 (12)	0.0880 (16)	0.0151 (11)	−0.0086 (13)	−0.0162 (11)
C7	0.0657 (11)	0.0528 (11)	0.0494 (9)	0.0014 (9)	0.0058 (8)	−0.0109 (8)
C8	0.0714 (12)	0.0496 (11)	0.0441 (9)	0.0032 (9)	−0.0005 (8)	−0.0074 (8)
C9	0.0542 (10)	0.0505 (10)	0.0416 (8)	−0.0067 (8)	0.0022 (7)	−0.0085 (7)
C10	0.0502 (9)	0.0462 (9)	0.0384 (7)	−0.0065 (7)	0.0006 (6)	−0.0016 (7)
C11	0.0612 (11)	0.0578 (11)	0.0405 (8)	−0.0055 (9)	−0.0066 (7)	−0.0034 (8)
C12	0.0793 (14)	0.0593 (12)	0.0532 (10)	0.0047 (10)	−0.0170 (9)	0.0061 (9)
C13	0.0935 (15)	0.0495 (12)	0.0615 (11)	0.0115 (11)	−0.0135 (11)	0.0028 (9)
C14	0.0893 (14)	0.0453 (10)	0.0466 (9)	0.0052 (10)	−0.0090 (9)	−0.0045 (8)
C15	0.0603 (10)	0.0439 (9)	0.0369 (7)	−0.0039 (8)	−0.0040 (7)	0.0006 (7)
C16	0.0968 (15)	0.0458 (10)	0.0446 (9)	−0.0043 (10)	−0.0178 (9)	−0.0066 (8)
C17	0.0779 (13)	0.0559 (12)	0.0475 (9)	−0.0123 (10)	−0.0173 (9)	−0.0022 (8)
C18	0.0674 (11)	0.0611 (12)	0.0414 (8)	−0.0094 (9)	−0.0101 (8)	−0.0029 (8)
C19	0.0799 (13)	0.0482 (11)	0.0452 (9)	−0.0041 (9)	−0.0111 (9)	−0.0047 (8)
C20	0.0539 (10)	0.0498 (10)	0.0417 (8)	0.0056 (8)	0.0022 (7)	0.0074 (7)
C21	0.0471 (9)	0.0440 (9)	0.0415 (8)	0.0005 (7)	−0.0035 (6)	0.0086 (7)
C22	0.0489 (10)	0.0632 (12)	0.0565 (10)	−0.0022 (8)	−0.0014 (8)	0.0116 (9)
C23	0.0458 (8)	0.0368 (8)	0.0377 (7)	0.0003 (6)	−0.0057 (6)	0.0084 (6)
C24	0.0482 (9)	0.0373 (8)	0.0397 (7)	0.0006 (7)	−0.0046 (6)	0.0060 (6)
C25	0.0482 (9)	0.0525 (11)	0.0560 (10)	−0.0046 (8)	−0.0082 (7)	0.0065 (8)
C26	0.0476 (10)	0.0700 (13)	0.0613 (11)	0.0019 (9)	0.0047 (8)	0.0082 (10)
C27	0.0614 (11)	0.0666 (13)	0.0473 (9)	0.0066 (9)	0.0075 (8)	0.0010 (8)
C28	0.0569 (10)	0.0498 (10)	0.0401 (8)	0.0007 (8)	−0.0051 (7)	0.0022 (7)
N1	0.0575 (8)	0.0443 (8)	0.0380 (7)	0.0004 (6)	−0.0065 (6)	0.0009 (6)
O1	0.1221 (14)	0.0712 (10)	0.0562 (8)	0.0217 (9)	−0.0091 (8)	−0.0221 (7)
O2	0.0842 (9)	0.0449 (7)	0.0396 (6)	0.0066 (6)	−0.0160 (6)	−0.0055 (5)
O3	0.0594 (8)	0.1004 (12)	0.0651 (9)	−0.0151 (8)	−0.0157 (7)	−0.0039 (8)
Cl1	0.1481 (7)	0.0834 (5)	0.0832 (4)	0.0471 (5)	−0.0170 (4)	−0.0014 (3)

C1—C2	1.369 (3)	C16—C17	1.513 (3)
C1—C6	1.374 (3)	C16—H16A	0.9700
C1—Cl1	1.742 (2)	C16—H16B	0.9700
C2—C3	1.378 (3)	C17—C18	1.506 (3)
C2—H2	0.9300	C17—H17A	0.9700
C3—C4	1.388 (3)	C17—H17B	0.9700
C3—H3	0.9300	C18—C19	1.520 (3)
C4—C5	1.387 (3)	C18—H18A	0.9700
C4—C7	1.489 (3)	C18—H18B	0.9700
C5—C6	1.377 (3)	C19—N1	1.462 (2)
C5—H5	0.9300	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—O1	1.223 (2)	C20—N1	1.352 (2)
C7—C8	1.475 (3)	C20—C21	1.375 (2)
C8—C9	1.326 (3)	C20—H20	0.9300
C8—H8	0.9300	C21—C23	1.434 (2)
C9—C10	1.450 (3)	C21—C22	1.434 (2)
C9—H9	0.9300	C22—O3	1.211 (2)
C10—C11	1.398 (2)	C22—H22	0.9300
C10—C15	1.415 (2)	C23—C28	1.396 (2)
C11—C12	1.370 (3)	C23—C24	1.405 (2)
C11—H11	0.9300	C24—N1	1.387 (2)
C12—C13	1.371 (3)	C24—C25	1.390 (2)
C12—H12	0.9300	C25—C26	1.372 (3)
C13—C14	1.380 (3)	C25—H25	0.9300
C13—H13	0.9300	C26—C27	1.392 (3)
C14—C15	1.383 (3)	C26—H26	0.9300
C14—H14	0.9300	C27—C28	1.380 (3)
C15—O2	1.3583 (19)	C27—H27	0.9300
C16—O2	1.434 (2)	C28—H28	0.9300
C2—C1—C6	121.0 (2)	H16A—C16—H16B	108.6
C2—C1—Cl1	119.29 (18)	C18—C17—C16	113.45 (17)
C6—C1—Cl1	119.75 (17)	C18—C17—H17A	108.9
C1—C2—C3	119.1 (2)	C16—C17—H17A	108.9
C1—C2—H2	120.5	C18—C17—H17B	108.9
C3—C2—H2	120.5	C16—C17—H17B	108.9
C2—C3—C4	121.55 (19)	H17A—C17—H17B	107.7
C2—C3—H3	119.2	C17—C18—C19	113.20 (16)
C4—C3—H3	119.2	C17—C18—H18A	108.9
C5—C4—C3	117.70 (19)	C19—C18—H18A	108.9
C5—C4—C7	118.95 (17)	C17—C18—H18B	108.9
C3—C4—C7	123.30 (17)	C19—C18—H18B	108.9
C6—C5—C4	121.2 (2)	H18A—C18—H18B	107.8
C6—C5—H5	119.4	N1—C19—C18	113.48 (15)
C4—C5—H5	119.4	N1—C19—H19A	108.9
C1—C6—C5	119.4 (2)	C18—C19—H19A	108.9
C1—C6—H6	120.3	N1—C19—H19B	108.9
C5—C6—H6	120.3	C18—C19—H19B	108.9
O1—C7—C8	121.14 (18)	H19A—C19—H19B	107.7
O1—C7—C4	120.06 (17)	N1—C20—C21	110.35 (15)
C8—C7—C4	118.80 (15)	N1—C20—H20	124.8
C9—C8—C7	120.95 (16)	C21—C20—H20	124.8
C9—C8—H8	119.5	C20—C21—C23	106.59 (14)
C7—C8—H8	119.5	C20—C21—C22	124.54 (17)
C8—C9—C10	131.29 (16)	C23—C21—C22	128.79 (16)
C8—C9—H9	114.4	O3—C22—C21	125.64 (18)
C10—C9—H9	114.4	O3—C22—H22	117.2
C11—C10—C15	116.86 (16)	C21—C22—H22	117.2
C11—C10—C9	117.85 (15)	C28—C23—C24	119.25 (15)
C15—C10—C9	125.28 (15)	C28—C23—C21	134.26 (15)
C12—C11—C10	122.66 (17)	C24—C23—C21	106.49 (14)
C12—C11—H11	118.7	N1—C24—C25	129.92 (15)
C10—C11—H11	118.7	N1—C24—C23	107.87 (14)
C11—C12—C13	119.26 (18)	C25—C24—C23	122.20 (15)
C11—C12—H12	120.4	C26—C25—C24	117.22 (17)
C13—C12—H12	120.4	C26—C25—H25	121.4
C12—C13—C14	120.61 (19)	C24—C25—H25	121.4
C12—C13—H13	119.7	C25—C26—C27	121.62 (18)
C14—C13—H13	119.7	C25—C26—H26	119.2
C13—C14—C15	120.43 (17)	C27—C26—H26	119.2
C13—C14—H14	119.8	C28—C27—C26	121.32 (17)
C15—C14—H14	119.8	C28—C27—H27	119.3
O2—C15—C14	123.39 (15)	C26—C27—H27	119.3
O2—C15—C10	116.42 (15)	C27—C28—C23	118.38 (16)
C14—C15—C10	120.19 (16)	C27—C28—H28	120.8
O2—C16—C17	106.49 (16)	C23—C28—H28	120.8
O2—C16—H16A	110.4	C20—N1—C24	108.69 (14)
C17—C16—H16A	110.4	C20—N1—C19	125.67 (15)
O2—C16—H16B	110.4	C24—N1—C19	125.58 (15)
C17—C16—H16B	110.4	C15—O2—C16	118.49 (14)
C6—C1—C2—C3	−3.7 (4)	C17—C18—C19—N1	−60.3 (2)
Cl1—C1—C2—C3	176.83 (19)	N1—C20—C21—C23	0.29 (19)
C1—C2—C3—C4	1.4 (4)	N1—C20—C21—C22	−176.78 (16)
C2—C3—C4—C5	1.9 (3)	C20—C21—C22—O3	176.1 (2)
C2—C3—C4—C7	179.3 (2)	C23—C21—C22—O3	−0.3 (3)
C3—C4—C5—C6	−2.9 (3)	C20—C21—C23—C28	179.59 (18)
C7—C4—C5—C6	179.5 (2)	C22—C21—C23—C28	−3.5 (3)
C2—C1—C6—C5	2.7 (4)	C20—C21—C23—C24	−0.24 (18)
Cl1—C1—C6—C5	−177.9 (2)	C22—C21—C23—C24	176.67 (17)
C4—C5—C6—C1	0.7 (4)	C28—C23—C24—N1	−179.75 (14)
C5—C4—C7—O1	12.0 (3)	C21—C23—C24—N1	0.11 (17)
C3—C4—C7—O1	−165.4 (2)	C28—C23—C24—C25	0.9 (2)
C5—C4—C7—C8	−167.82 (19)	C21—C23—C24—C25	−179.28 (15)
C3—C4—C7—C8	14.8 (3)	N1—C24—C25—C26	−179.55 (17)
O1—C7—C8—C9	2.8 (3)	C23—C24—C25—C26	−0.3 (3)
C4—C7—C8—C9	−177.42 (18)	C24—C25—C26—C27	−0.6 (3)
C7—C8—C9—C10	−178.63 (18)	C25—C26—C27—C28	0.9 (3)
C8—C9—C10—C11	172.6 (2)	C26—C27—C28—C23	−0.3 (3)
C8—C9—C10—C15	−8.3 (3)	C24—C23—C28—C27	−0.5 (2)
C15—C10—C11—C12	0.3 (3)	C21—C23—C28—C27	179.67 (18)
C9—C10—C11—C12	179.50 (18)	C21—C20—N1—C24	−0.22 (19)
C10—C11—C12—C13	−0.3 (3)	C21—C20—N1—C19	177.14 (15)
C11—C12—C13—C14	−0.3 (4)	C25—C24—N1—C20	179.39 (17)
C12—C13—C14—C15	0.9 (4)	C23—C24—N1—C20	0.06 (18)
C13—C14—C15—O2	179.22 (19)	C25—C24—N1—C19	2.0 (3)
C13—C14—C15—C10	−0.9 (3)	C23—C24—N1—C19	−177.31 (15)
C11—C10—C15—O2	−179.82 (15)	C18—C19—N1—C20	109.0 (2)
C9—C10—C15—O2	1.1 (3)	C18—C19—N1—C24	−74.1 (2)
C11—C10—C15—C14	0.3 (3)	C14—C15—O2—C16	5.0 (3)
C9—C10—C15—C14	−178.79 (18)	C10—C15—O2—C16	−174.84 (17)
O2—C16—C17—C18	68.2 (2)	C17—C16—O2—C15	176.03 (16)
C16—C17—C18—C19	−175.60 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.93	2.26	2.850 (2)	121
C9—H9···O1	0.93	2.42	2.791 (2)	104
C20—H20···O1i	0.93	2.52	3.374 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2	0.93	2.26	2.850 (2)	121
C20—H20⋯O1i	0.93	2.52	3.374 (2)	152

Symmetry code: (i) .