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

In the title compound, C(22)H(12)Cl(2)N(4)O, 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 meth-oxy group is coplanar with the pyridine ring. In the crystal structure N-H⋯N inter-molecular hydrogen bonds link the mol-ecules into C(10) chains running along [011]. Intramolec-ular 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 = 419.26

Triclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.05

3401 reflections

267 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.37 e Å−3

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 ▶).

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

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

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

C22H12Cl2N4O	Z = 2
Mr = 419.26	F(000) = 428
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0487P)2 + 0.3783P] where P = (Fo2 + 2Fc2)/3
3401 reflections	(Δ/σ)max = 0.005
267 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.37 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	−0.20213 (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*

	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)

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)

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)

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) .