4-(2,4-Dichlorophenyl)-2-(1H-indol-3-yl)-6-methoxypyridine-3,5-dicarbonitrile

Ramesh, P.; Subbiahpandi, A.; Thirumurugan, P.; Perumal, P.T.; Ponnuswamy, M.N.

doi:10.1107/S1600536808027670

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1892

doi:10.1107/S1600536808027670

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4-(2,4-Dichlorophenyl)-2-(1H-indol-3-yl)-6-methoxypyridine-3,5-dicarbonitrile

P. Ramesh,^a A. Subbiahpandi,^a P. Thirumurugan,^b P. T. Perumal ^b and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 11 August 2008; accepted 28 August 2008; online 6 September 2008)

In the title compound, C₂₂H₁₂Cl₂N₄O, the indole ring system and the benzene ring form dihedral angles of 21.18 (7)° and 68.43 (8)°, respectively, with the pyridine ring. The methoxy group is coplanar with the pyridine ring. In the crystal structure N—H⋯N intermolecular hydrogen bonds link the molecules into C(10) chains running along [011]. Intramolecular C—H⋯N hydrogen bonds are also observed.

Related literature

For related literature, see: James et al. (1991 ); Kobayashi et al. (1991 ); Rajeswaran et al. (1999 ). For graph-set analysis of hydrogen-bonding patterns, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₂H₁₂Cl₂N₄O
M_r = 419.26
Triclinic, $[P \overline 1]$
a = 9.5394 (2) Å
b = 10.0358 (2) Å
c = 11.1739 (3) Å
α = 111.994 (1)°
β = 97.303 (1)°
γ = 93.715 (1)°
V = 976.46 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 (2) K
0.58 × 0.40 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.821, T_max = 0.907
10781 measured reflections
3401 independent reflections
3019 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.096
S = 1.05
3401 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N1	0.93	2.56	3.045 (2)	113
C15—H15⋯N17	0.93	2.56	3.282 (2)	135
N14—H14⋯N25ⁱ	0.83 (2)	2.22 (2)	2.996 (2)	156 (2)
Symmetry code: (i) x, y+1, z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, (1997 )); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027670/ci2655sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027670/ci2655Isup2.hkl

checkCIF report

Comment top

Spiro compounds are the naturally occurring substances which exibit many biological properties (Kobayashi et al., 1991; James et al., 1991). Indoles have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al.., 1999). In view of this an X-ray diffraction study of the title compound was carrid out.

The indole ring system is essentially planar. The indole ring system and the benzene ring form dihedral angles of 21.18 (7)° and 68.43 (8)°, respectively, with the pyridine ring. The methoxy group is coplanar with the pyridine ring, with the C26—O1—C6—N1 torsion angle being 4.9 (2)°. C—H···N type intramolecular hydrogen bonds are observed in the molecular structure.

In the crystal structure N—H···N intermolecular hydrogen bonds link the molecules into C(10) chains (Bernstein et al., 1995) running along the [0 1 1].

Related literature top

For related literature, see: James et al. (1991); Kobayashi et al. (1991); Rajeswaran et al. (1999). For graph-set analysis of hydrogen-bonding patterns, see: Bernstein et al. (1995).

Experimental top

A mixture of 3-cyanoacetyl indole (1 mmol), 2,4 dichlorobenzaldehyde (1 mmol) and sodium hydroxide (1.2 mmol) in methanol was refluxed. After 15 min malanonitrile (1 mmol) was added and the reflux was continued for 4 h. After the completion of the reaction (as monitored by TLC), it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuo. The crude product was chromatographed and isolated in 78% yield (90:10, petroleum ether: ethyl acetate). The crude product was recrystallized in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, (1997)); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

4-(2,4-Dichlorophenyl)-2-(1H-indol-3-yl)-6-methoxypyridine-3,5- dicarbonitrile top

Crystal data top

C₂₂H₁₂Cl₂N₄O	Z = 2
M_r = 419.26	F(000) = 428
Triclinic, P1	D_x = 1.426 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5394 (2) Å	Cell parameters from 2563 reflections
b = 10.0358 (2) Å	θ = 2.2–25.0°
c = 11.1739 (3) Å	µ = 0.35 mm⁻¹
α = 111.994 (1)°	T = 298 K
β = 97.303 (1)°	Block, yellow
γ = 93.715 (1)°	0.58 × 0.40 × 0.28 mm
V = 976.46 (4) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3401 independent reflections
Radiation source: fine-focus sealed tube	3019 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
T_min = 0.821, T_max = 0.907	k = −11→10
10781 measured reflections	l = −11→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0487P)² + 0.3783P] where P = (F_o² + 2F_c²)/3
3401 reflections	(Δ/σ)_max = 0.005
267 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₂H₁₂Cl₂N₄O	γ = 93.715 (1)°
M_r = 419.26	V = 976.46 (4) Å³
Triclinic, P1	Z = 2
a = 9.5394 (2) Å	Mo Kα radiation
b = 10.0358 (2) Å	µ = 0.35 mm⁻¹
c = 11.1739 (3) Å	T = 298 K
α = 111.994 (1)°	0.58 × 0.40 × 0.28 mm
β = 97.303 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3401 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3019 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.907	R_int = 0.019
10781 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.29 e Å⁻³
3401 reflections	Δρ_min = −0.37 e Å⁻³
267 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	−0.20213 (5)	0.05813 (6)	0.06721 (6)	0.06710 (19)
Cl2	0.18710 (5)	0.43669 (6)	0.01921 (5)	0.05569 (16)
O1	0.71041 (12)	0.47517 (13)	0.22771 (11)	0.0440 (3)
N1	0.60609 (13)	0.63393 (14)	0.38834 (12)	0.0322 (3)
C2	0.49048 (16)	0.66990 (16)	0.44682 (14)	0.0294 (3)
C3	0.36036 (15)	0.57682 (16)	0.39683 (14)	0.0293 (3)
C4	0.34811 (16)	0.45252 (16)	0.28224 (14)	0.0294 (3)
C5	0.46814 (16)	0.42069 (17)	0.22319 (15)	0.0332 (4)
C6	0.59570 (16)	0.51473 (17)	0.28335 (15)	0.0327 (3)
C7	0.51214 (16)	0.80627 (17)	0.55884 (15)	0.0322 (3)
C8	0.62593 (17)	0.92294 (16)	0.58897 (15)	0.0332 (3)
C9	0.73824 (19)	0.94826 (18)	0.52844 (17)	0.0417 (4)
H9	0.7519	0.8801	0.4486	0.050*
C10	0.8286 (2)	1.0759 (2)	0.5888 (2)	0.0505 (5)
H10	0.9042	1.0927	0.5493	0.061*
C11	0.8089 (2)	1.18028 (19)	0.7078 (2)	0.0516 (5)
H11	0.8719	1.2651	0.7464	0.062*
C12	0.6985 (2)	1.16004 (19)	0.76875 (18)	0.0474 (4)
H12	0.6843	1.2300	0.8474	0.057*
C13	0.60840 (18)	1.03058 (18)	0.70822 (16)	0.0380 (4)
N14	0.49146 (17)	0.98300 (16)	0.74801 (15)	0.0456 (4)
H14	0.462 (2)	1.023 (2)	0.818 (2)	0.057 (6)*
C15	0.43425 (18)	0.85081 (18)	0.66041 (16)	0.0399 (4)
H15	0.3544	0.7974	0.6671	0.048*
C16	0.23671 (17)	0.61040 (17)	0.45772 (15)	0.0349 (4)
N17	0.13813 (16)	0.63647 (17)	0.50645 (16)	0.0519 (4)
C18	0.21094 (15)	0.35534 (16)	0.22670 (14)	0.0302 (3)
C19	0.15904 (18)	0.27834 (18)	0.29551 (16)	0.0380 (4)
H19	0.2100	0.2892	0.3759	0.046*
C20	0.03299 (19)	0.18576 (19)	0.24684 (18)	0.0441 (4)
H20	0.0002	0.1335	0.2932	0.053*
C21	−0.04298 (17)	0.17221 (18)	0.12898 (18)	0.0427 (4)
C22	0.00404 (17)	0.24803 (19)	0.05835 (17)	0.0425 (4)
H22	−0.0485	0.2383	−0.0211	0.051*
C23	0.13088 (17)	0.33881 (17)	0.10799 (15)	0.0353 (4)
C24	0.46601 (17)	0.29503 (19)	0.10682 (16)	0.0404 (4)
N25	0.46376 (18)	0.19450 (19)	0.01436 (16)	0.0597 (5)
C26	0.84527 (18)	0.5613 (2)	0.29323 (18)	0.0490 (5)
H26A	0.8435	0.6564	0.2920	0.073*
H26B	0.9201	0.5162	0.2491	0.073*
H26C	0.8619	0.5687	0.3822	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0368 (3)	0.0635 (3)	0.0759 (4)	−0.0164 (2)	0.0051 (2)	0.0037 (3)
Cl2	0.0581 (3)	0.0665 (3)	0.0449 (3)	−0.0046 (2)	−0.0027 (2)	0.0297 (2)
O1	0.0292 (6)	0.0475 (7)	0.0372 (6)	0.0012 (5)	0.0101 (5)	−0.0049 (5)
N1	0.0281 (7)	0.0327 (7)	0.0266 (7)	0.0013 (5)	0.0038 (5)	0.0017 (5)
C2	0.0310 (8)	0.0295 (7)	0.0237 (7)	0.0045 (6)	0.0040 (6)	0.0058 (6)
C3	0.0292 (8)	0.0296 (8)	0.0248 (7)	0.0043 (6)	0.0047 (6)	0.0053 (6)
C4	0.0286 (8)	0.0301 (8)	0.0251 (7)	0.0030 (6)	0.0010 (6)	0.0069 (6)
C5	0.0318 (8)	0.0322 (8)	0.0261 (8)	0.0027 (6)	0.0044 (6)	0.0008 (6)
C6	0.0292 (8)	0.0354 (8)	0.0272 (8)	0.0033 (6)	0.0059 (6)	0.0049 (6)
C7	0.0315 (8)	0.0308 (8)	0.0264 (8)	0.0031 (6)	0.0025 (6)	0.0031 (6)
C8	0.0358 (8)	0.0287 (8)	0.0286 (8)	0.0041 (6)	0.0000 (6)	0.0056 (6)
C9	0.0469 (10)	0.0356 (9)	0.0391 (9)	0.0028 (7)	0.0097 (8)	0.0099 (7)
C10	0.0497 (11)	0.0440 (10)	0.0567 (12)	−0.0032 (8)	0.0108 (9)	0.0190 (9)
C11	0.0547 (11)	0.0342 (9)	0.0547 (12)	−0.0084 (8)	−0.0026 (9)	0.0104 (8)
C12	0.0556 (11)	0.0327 (9)	0.0384 (10)	−0.0009 (8)	−0.0011 (8)	0.0002 (7)
C13	0.0412 (9)	0.0329 (8)	0.0309 (8)	0.0031 (7)	0.0012 (7)	0.0040 (7)
N14	0.0491 (9)	0.0395 (8)	0.0308 (8)	0.0010 (7)	0.0124 (7)	−0.0071 (6)
C15	0.0384 (9)	0.0378 (9)	0.0308 (8)	−0.0009 (7)	0.0071 (7)	−0.0006 (7)
C16	0.0324 (8)	0.0324 (8)	0.0305 (8)	−0.0003 (6)	0.0045 (7)	0.0027 (6)
N17	0.0397 (8)	0.0519 (9)	0.0508 (9)	0.0006 (7)	0.0172 (7)	0.0026 (7)
C18	0.0278 (8)	0.0282 (7)	0.0275 (8)	0.0042 (6)	0.0051 (6)	0.0026 (6)
C19	0.0364 (9)	0.0393 (9)	0.0333 (9)	0.0022 (7)	0.0036 (7)	0.0097 (7)
C20	0.0415 (9)	0.0404 (9)	0.0474 (10)	−0.0012 (7)	0.0133 (8)	0.0126 (8)
C21	0.0287 (8)	0.0380 (9)	0.0464 (10)	−0.0009 (7)	0.0060 (7)	0.0001 (7)
C22	0.0326 (9)	0.0467 (10)	0.0352 (9)	0.0020 (7)	−0.0033 (7)	0.0045 (8)
C23	0.0339 (8)	0.0361 (8)	0.0297 (8)	0.0039 (6)	0.0029 (6)	0.0067 (7)
C24	0.0306 (8)	0.0408 (9)	0.0350 (9)	−0.0004 (7)	0.0067 (7)	−0.0017 (8)
N25	0.0475 (9)	0.0546 (10)	0.0464 (10)	−0.0016 (7)	0.0124 (7)	−0.0152 (8)
C26	0.0291 (9)	0.0586 (11)	0.0441 (10)	−0.0027 (8)	0.0088 (7)	0.0032 (8)

Geometric parameters (Å, º) top

Cl1—C21	1.7345 (16)	C11—C12	1.369 (3)
Cl2—C23	1.7418 (17)	C11—H11	0.93
O1—C6	1.3363 (19)	C12—C13	1.390 (2)
O1—C26	1.443 (2)	C12—H12	0.93
N1—C6	1.3119 (19)	C13—N14	1.373 (2)
N1—C2	1.3533 (19)	N14—C15	1.347 (2)
C2—C3	1.417 (2)	N14—H14	0.83 (2)
C2—C7	1.448 (2)	C15—H15	0.93
C3—C4	1.399 (2)	C16—N17	1.142 (2)
C3—C16	1.432 (2)	C18—C19	1.388 (2)
C4—C5	1.389 (2)	C18—C23	1.390 (2)
C4—C18	1.491 (2)	C19—C20	1.384 (2)
C5—C6	1.411 (2)	C19—H19	0.93
C5—C24	1.429 (2)	C20—C21	1.374 (3)
C7—C15	1.385 (2)	C20—H20	0.93
C7—C8	1.452 (2)	C21—C22	1.378 (3)
C8—C9	1.396 (2)	C22—C23	1.382 (2)
C8—C13	1.404 (2)	C22—H22	0.93
C9—C10	1.378 (2)	C24—N25	1.139 (2)
C9—H9	0.93	C26—H26A	0.96
C10—C11	1.395 (3)	C26—H26B	0.96
C10—H10	0.93	C26—H26C	0.96

C6—O1—C26	117.54 (12)	N14—C13—C12	129.16 (16)
C6—N1—C2	119.61 (13)	N14—C13—C8	107.90 (14)
N1—C2—C3	119.97 (13)	C12—C13—C8	122.94 (16)
N1—C2—C7	115.10 (13)	C15—N14—C13	109.99 (14)
C3—C2—C7	124.94 (13)	C15—N14—H14	122.7 (15)
C4—C3—C2	120.27 (13)	C13—N14—H14	127.0 (15)
C4—C3—C16	118.28 (13)	N14—C15—C7	109.82 (15)
C2—C3—C16	121.39 (13)	N14—C15—H15	125.1
C5—C4—C3	118.09 (14)	C7—C15—H15	125.1
C5—C4—C18	120.99 (13)	N17—C16—C3	179.60 (19)
C3—C4—C18	120.91 (13)	C19—C18—C23	117.88 (14)
C4—C5—C6	118.03 (13)	C19—C18—C4	119.46 (14)
C4—C5—C24	121.96 (14)	C23—C18—C4	122.65 (14)
C6—C5—C24	119.99 (14)	C20—C19—C18	121.33 (16)
N1—C6—O1	120.15 (13)	C20—C19—H19	119.3
N1—C6—C5	123.88 (14)	C18—C19—H19	119.3
O1—C6—C5	115.97 (13)	C21—C20—C19	119.01 (17)
C15—C7—C2	128.05 (15)	C21—C20—H20	120.5
C15—C7—C8	106.02 (13)	C19—C20—H20	120.5
C2—C7—C8	125.90 (14)	C20—C21—C22	121.45 (15)
C9—C8—C13	118.23 (15)	C20—C21—Cl1	119.68 (15)
C9—C8—C7	135.50 (14)	C22—C21—Cl1	118.87 (14)
C13—C8—C7	106.27 (14)	C21—C22—C23	118.65 (16)
C10—C9—C8	118.98 (16)	C21—C22—H22	120.7
C10—C9—H9	120.5	C23—C22—H22	120.7
C8—C9—H9	120.5	C22—C23—C18	121.66 (16)
C9—C10—C11	121.41 (18)	C22—C23—Cl2	118.11 (13)
C9—C10—H10	119.3	C18—C23—Cl2	120.21 (12)
C11—C10—H10	119.3	N25—C24—C5	179.6 (2)
C12—C11—C10	121.15 (17)	O1—C26—H26A	109.5
C12—C11—H11	119.4	O1—C26—H26B	109.5
C10—C11—H11	119.4	H26A—C26—H26B	109.5
C11—C12—C13	117.28 (16)	O1—C26—H26C	109.5
C11—C12—H12	121.4	H26A—C26—H26C	109.5
C13—C12—H12	121.4	H26B—C26—H26C	109.5

C6—N1—C2—C3	1.9 (2)	C8—C9—C10—C11	−0.8 (3)
C6—N1—C2—C7	−177.70 (14)	C9—C10—C11—C12	−0.3 (3)
N1—C2—C3—C4	−4.2 (2)	C10—C11—C12—C13	0.9 (3)
C7—C2—C3—C4	175.33 (14)	C11—C12—C13—N14	179.70 (19)
N1—C2—C3—C16	178.90 (14)	C11—C12—C13—C8	−0.5 (3)
C7—C2—C3—C16	−1.6 (2)	C9—C8—C13—N14	179.26 (15)
C2—C3—C4—C5	2.7 (2)	C7—C8—C13—N14	−0.18 (19)
C16—C3—C4—C5	179.73 (15)	C9—C8—C13—C12	−0.6 (3)
C2—C3—C4—C18	−178.57 (14)	C7—C8—C13—C12	179.97 (16)
C16—C3—C4—C18	−1.6 (2)	C12—C13—N14—C15	179.98 (19)
C3—C4—C5—C6	0.8 (2)	C8—C13—N14—C15	0.1 (2)
C18—C4—C5—C6	−177.91 (14)	C13—N14—C15—C7	0.0 (2)
C3—C4—C5—C24	179.19 (15)	C2—C7—C15—N14	177.82 (16)
C18—C4—C5—C24	0.5 (2)	C8—C7—C15—N14	−0.1 (2)
C2—N1—C6—O1	−177.39 (14)	C5—C4—C18—C19	112.23 (18)
C2—N1—C6—C5	1.9 (2)	C3—C4—C18—C19	−66.4 (2)
C26—O1—C6—N1	4.9 (2)	C5—C4—C18—C23	−68.3 (2)
C26—O1—C6—C5	−174.42 (16)	C3—C4—C18—C23	113.05 (17)
C4—C5—C6—N1	−3.3 (3)	C23—C18—C19—C20	1.2 (2)
C24—C5—C6—N1	178.32 (16)	C4—C18—C19—C20	−179.29 (15)
C4—C5—C6—O1	176.04 (15)	C18—C19—C20—C21	−1.1 (3)
C24—C5—C6—O1	−2.4 (2)	C19—C20—C21—C22	0.3 (3)
N1—C2—C7—C15	−158.09 (17)	C19—C20—C21—Cl1	−179.34 (13)
C3—C2—C7—C15	22.4 (3)	C20—C21—C22—C23	0.3 (3)
N1—C2—C7—C8	19.4 (2)	Cl1—C21—C22—C23	179.99 (12)
C3—C2—C7—C8	−160.10 (15)	C21—C22—C23—C18	−0.2 (2)
C15—C7—C8—C9	−179.15 (19)	C21—C22—C23—Cl2	−178.73 (13)
C2—C7—C8—C9	2.9 (3)	C19—C18—C23—C22	−0.5 (2)
C15—C7—C8—C13	0.16 (18)	C4—C18—C23—C22	179.96 (14)
C2—C7—C8—C13	−177.80 (15)	C19—C18—C23—Cl2	177.97 (12)
C13—C8—C9—C10	1.2 (3)	C4—C18—C23—Cl2	−1.5 (2)
C7—C8—C9—C10	−179.58 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1	0.93	2.56	3.045 (2)	113
C15—H15···N17	0.93	2.56	3.282 (2)	135
N14—H14···N25ⁱ	0.83 (2)	2.22 (2)	2.996 (2)	156 (2)

Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₂Cl₂N₄O
M_r	419.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.5394 (2), 10.0358 (2), 11.1739 (3)
α, β, γ (°)	111.994 (1), 97.303 (1), 93.715 (1)
V (Å³)	976.46 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.58 × 0.40 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.821, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	10781, 3401, 3019
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.05
No. of reflections	3401
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.37

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, (1997)), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1	0.93	2.56	3.045 (2)	113
C15—H15···N17	0.93	2.56	3.282 (2)	135
N14—H14···N25ⁱ	0.83 (2)	2.22 (2)	2.996 (2)	156 (2)

Symmetry code: (i) x, y+1, z+1.

Acknowledgements

PR thanks V. Ramkumar, Department of Chemistry, IIT-Madras, Chennai, India, for his help with the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
James, D., Kunz, H. B. & Faulkner, D. (1991). J. Nat. Prod. 54, 1137–1140. CrossRef PubMed CAS Web of Science Google Scholar
Kobayashi, J., Tsuda, M., Agmi, K., Shigmori, H., Ishibashi, M., Sasaki, T. & Mikami, Y. (1991). Tetrahedron, 47, 6617–6622. CrossRef CAS Web of Science Google Scholar
Rajeswaran, W. G., Labroo, R. B., Cohen, L. A. & King, M. M. (1999). J. Org. Chem. 64, 1369–1371. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 10| October 2008| Page o1892

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

4-(2,4-Di­chloro­phenyl)-2-(1H-indol-3-yl)-6-methoxypyridine-3,5-dicarbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(2,4-Dichlorophenyl)-2-(1H-indol-3-yl)-6-methoxypyridine-3,5-dicarbonitrile