1-(4-{2-[(E)-3-(4-Chloro­phen­yl)-3-oxo­prop-1-en-1-yl]phen­oxy}but­yl)-1H-indole-3-carbaldehyde

Paramasivam, S.; Purushothaman, S.; Seshadri, P.R.; Raghunathan, R.

doi:10.1107/S1600536813002456

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o314-o315

doi:10.1107/S1600536813002456

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1-(4-{2-[(E)-3-(4-Chlorophenyl)-3-oxoprop-1-en-1-yl]phenoxy}butyl)-1H-indole-3-carbaldehyde

S. Paramasivam,^a Santhanagopalan Purushothaman,^b P. R. Seshadri ^a ^* and Raghavachary Raghunathan ^b

^aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 15 January 2013; accepted 24 January 2013; online 31 January 2013)

In the title compound, C₂₈H₂₄ClNO₃, 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 molecular structure is stabilized by a weak intramolecular C—H⋯O interaction. In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules into inversion dimers with an R₂²(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_r = 457.93
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.145
S = 1.03
5782 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.46 e Å⁻³

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) -x, -y+1, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813002456/kp2444sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813002456/kp2444Isup3.cml

checkCIF report

Comment top

Indole derivatives exhibit antioxidant (Olgen & Coban, 2003), central nervous system depressant and muscle relaxant properties (Ho et al., 1986), antifungicidal (Joshi & Chand, 1982), antimicrobial, antiinflammatory and antiimplantation (Rodriguez et al., 1985), antibacterial (Okabe & Adachi, 1998) and antihypertensive (Merck, 1973) activities. Against this background, the title compound was chosen for X-ray structure analysis (Fig. 1).

The indole ring is planar and it makes the dihedral angle with the chlorophenyl ring of 78.62 (05)°.

The sum of the bond angles around N1 [359.94 (44)°] indicates sp² hybridization (Beddoes et al., 1986). The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Paramasivam et al., 2012).

The molecular structure is stabilised by a weak C—H···O intramolecular interaction and the crystal packing reveals a weak C—H···O hydrogen bonds (Fig. 2). In the crystal structure, the molecules at (x, y, z) and (- x, - y + 1, - z + 2) are linked by C20—H20···O1 hydrogen bond, generating a centrosymmetric dimeric ring motif R₂²(14) (Bernstein et al., 1995).

Related literature top

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 top

2 g (13.7 mmol) of 1H-indole-3-carbaldehyde in 25 mL dry DMF and anhydrous potassium carbonate (2 g, 13.7 mmol) were stirred for 15 min at room temperature followed by addition of 5.4 g (13.7 mmol) of (E)-3-(2-(4-bromobutoxy)phenyl)-1-(4-chlorophenyl)prop-2-en-1-one in 30 mL dry DMF with continued stirring for about 3 h at room temperature. After the completion of the reaction as evidenced from TLC, the solvent was filtered into crushed ice and extracted with chloroform. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the residue eluting with hexane/ethyl acetate mixture (8:2) gave pure (E)-1-(4-(2-(3-(4-chlorophenyl)-3-oxoprop-1-enyl)phenoxy)butyl)-1H-indole-3-carbaldehyde in good yield.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown by dashed lines.

1-(4-{2-[(E)-3-(4-Chlorophenyl)-3-oxoprop-1-en-1-yl]phenoxy}butyl)-1H-indole-3-carbaldehyde top

Crystal data top

C₂₈H₂₄ClNO₃	F(000) = 960
M_r = 457.93	monoclinic
Monoclinic, P2₁/n	D_x = 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

Data collection top

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

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0591P)² + 0.7822P] where P = (F_o² + 2F_c²)/3
5782 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₈H₂₄ClNO₃	V = 2318.89 (13) Å³
M_r = 457.93	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7126 (3) Å	µ = 0.20 mm⁻¹
b = 19.1311 (6) Å	T = 298 K
c = 13.9338 (4) Å	0.20 × 0.20 × 0.20 mm
β = 93.198 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	4060 reflections with I > 2σ(I)
22253 measured reflections	R_int = 0.026
5782 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.03	Δρ_max = 0.39 e Å⁻³
5782 reflections	Δρ_min = −0.46 e Å⁻³
298 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄ClNO₃
M_r	457.93
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.7126 (3), 19.1311 (6), 13.9338 (4)
β (°)	93.198 (2)
V (Å³)	2318.89 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22253, 5782, 4060
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.145, 1.03
No. of reflections	5782
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.46

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windowa (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.93	2.26	2.850 (2)	120.8
C20—H20···O1ⁱ	0.93	2.52	3.374 (2)	152.0

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797. CSD CrossRef Google Scholar
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Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 69| Part 2| February 2013| Pages o314-o315

doi:10.1107/S1600536813002456

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

1-(4-{2-[(E)-3-(4-Chloro­phen­yl)-3-oxo­prop-1-en-1-yl]phen­­oxy}but­yl)-1H-indole-3-carbaldehyde

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(4-{2-[(E)-3-(4-Chlorophenyl)-3-oxoprop-1-en-1-yl]phenoxy}butyl)-1H-indole-3-carbaldehyde