4-(2,4-Dichlorophenyl)-2-(1H-indol-3-yl)-6-(2-pyridyl)-1,4-dihydropyridine-4-carbonitrile.

The title compound, C(25)H(16)Cl(2)N(4), has intra-molecular N-H⋯N and C-H⋯Cl hydrogen bonds. In the crystal structure, mol-ecules are linked through N-H⋯N hydrogen bonds, forming a centrosymmetric R(2) (2)(16) dimer.

Related literature

For related literature, see: Beddoes et al. (1986 ▶); Bernstein et al. (1995 ▶); Harris & Uhle (1960 ▶); Ho et al. (1986 ▶); Rajeswaran et al. (1999 ▶); Stevenson et al. (2000 ▶).

Experimental

Crystal data

C25H16Cl2N4

M = 443.32

Triclinic,

a = 8.0158 (9) Å

b = 10.0261 (12) Å

c = 14.3653 (17) Å

α = 72.260 (6)°

β = 79.420 (6)°

γ = 78.224 (6)°

V = 1067.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 298 (2) K

0.35 × 0.32 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.895, T max = 0.915

12383 measured reflections

3707 independent reflections

3172 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.140

S = 1.08

3707 reflections

288 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.64 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/S1600536808027669/bt2767sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027669/bt2767Isup2.hkl

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

C25H16Cl2N4	Z = 2
Mr = 443.32	F(000) = 456
Triclinic, P1	Dx = 1.379 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0158 (9) Å	Cell parameters from 2900 reflections
b = 10.0261 (12) Å	θ = 2.2–25.0°
c = 14.3653 (17) Å	µ = 0.33 mm−1
α = 72.260 (6)°	T = 298 K
β = 79.420 (6)°	Block, yellow
γ = 78.224 (6)°	0.35 × 0.32 × 0.28 mm
V = 1067.3 (2) Å3

Bruker APEX2 CCD area-detector diffractometer	3707 independent reflections
Radiation source: fine-focus sealed tube	3172 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→7
Tmin = 0.895, Tmax = 0.915	k = −11→11
12383 measured reflections	l = −17→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0719P)2 + 0.5551P] where P = (Fo2 + 2Fc2)/3
3707 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.64 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	0.65524 (10)	0.88516 (11)	0.55182 (6)	0.0861 (3)
Cl2	1.32340 (10)	0.67807 (10)	0.50447 (5)	0.0832 (3)
N1	0.7936 (2)	0.98325 (19)	0.91511 (14)	0.0411 (4)
H1	0.821 (3)	0.993 (3)	0.966 (2)	0.055 (8)*
C2	0.7078 (3)	0.8757 (2)	0.92099 (15)	0.0342 (4)
C3	0.6640 (3)	0.8668 (2)	0.83578 (15)	0.0362 (5)
C4	0.7222 (3)	0.9620 (2)	0.73464 (15)	0.0373 (5)
H4	0.6248	0.9910	0.6966	0.045*
C5	0.7668 (3)	1.0937 (2)	0.74732 (16)	0.0412 (5)
H5	0.7692	1.1738	0.6936	0.049*
C6	0.8027 (3)	1.0996 (2)	0.83236 (15)	0.0359 (5)
C7	0.6707 (3)	0.7807 (2)	1.01918 (15)	0.0357 (5)
C8	0.6776 (3)	0.8008 (2)	1.11452 (15)	0.0355 (4)
C9	0.7107 (3)	0.9087 (2)	1.14899 (17)	0.0426 (5)
H9	0.7337	0.9946	1.1049	0.051*
C10	0.7087 (3)	0.8860 (3)	1.24827 (18)	0.0515 (6)
H10	0.7316	0.9572	1.2709	0.062*
C11	0.6732 (3)	0.7589 (3)	1.31624 (18)	0.0553 (6)
H11	0.6743	0.7465	1.3830	0.066*
C12	0.6369 (3)	0.6519 (3)	1.28621 (17)	0.0523 (6)
H12	0.6108	0.5677	1.3314	0.063*
C13	0.6405 (3)	0.6741 (2)	1.18565 (16)	0.0408 (5)
N14	0.6121 (3)	0.5841 (2)	1.13699 (14)	0.0475 (5)
H14	0.586 (3)	0.503 (3)	1.1635 (19)	0.050 (7)*
C15	0.6302 (3)	0.6468 (2)	1.03934 (16)	0.0430 (5)
H15	0.6172	0.6054	0.9919	0.052*
C16	0.5542 (3)	0.7736 (2)	0.83477 (16)	0.0433 (5)
N17	0.4654 (3)	0.7028 (2)	0.82628 (17)	0.0636 (6)
C18	0.8703 (3)	0.8858 (2)	0.67753 (15)	0.0365 (5)
C19	0.8534 (3)	0.8496 (3)	0.59441 (17)	0.0455 (5)
C20	0.9908 (3)	0.7851 (3)	0.54127 (18)	0.0548 (6)
H20	0.9761	0.7629	0.4853	0.066*
C21	1.1491 (3)	0.7547 (3)	0.57292 (17)	0.0522 (6)
C22	1.1726 (3)	0.7853 (3)	0.65559 (18)	0.0537 (6)
H22	1.2802	0.7628	0.6770	0.064*
C23	1.0333 (3)	0.8503 (3)	0.70659 (17)	0.0474 (6)
H23	1.0492	0.8713	0.7628	0.057*
C24	0.8451 (3)	1.2263 (2)	0.85058 (16)	0.0382 (5)
C25	0.8700 (4)	1.3490 (2)	0.77569 (19)	0.0540 (6)
H25	0.8621	1.3543	0.7108	0.065*
C26	0.9063 (4)	1.4627 (3)	0.7986 (2)	0.0614 (7)
H26	0.9234	1.5458	0.7495	0.074*
C27	0.9171 (3)	1.4520 (3)	0.8944 (2)	0.0580 (7)
H27	0.9407	1.5276	0.9119	0.070*
C28	0.8923 (3)	1.3271 (3)	0.9640 (2)	0.0560 (6)
H28	0.9000	1.3201	1.0292	0.067*
N29	0.8574 (3)	1.2145 (2)	0.94397 (14)	0.0465 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0591 (4)	0.1440 (8)	0.0794 (5)	0.0098 (4)	−0.0343 (4)	−0.0684 (6)
Cl2	0.0690 (5)	0.1084 (7)	0.0464 (4)	0.0200 (4)	0.0061 (3)	−0.0138 (4)
N1	0.0546 (11)	0.0394 (10)	0.0346 (10)	−0.0202 (8)	−0.0125 (8)	−0.0056 (8)
C2	0.0346 (10)	0.0320 (10)	0.0376 (11)	−0.0075 (8)	−0.0042 (8)	−0.0106 (8)
C3	0.0383 (11)	0.0334 (11)	0.0389 (11)	−0.0084 (8)	−0.0066 (9)	−0.0105 (9)
C4	0.0413 (11)	0.0390 (11)	0.0337 (11)	−0.0072 (9)	−0.0105 (8)	−0.0094 (9)
C5	0.0524 (13)	0.0329 (11)	0.0370 (12)	−0.0100 (9)	−0.0069 (9)	−0.0051 (9)
C6	0.0386 (11)	0.0312 (10)	0.0374 (11)	−0.0092 (8)	−0.0032 (8)	−0.0074 (9)
C7	0.0372 (11)	0.0341 (10)	0.0370 (11)	−0.0086 (8)	−0.0029 (8)	−0.0109 (9)
C8	0.0335 (10)	0.0361 (11)	0.0363 (11)	−0.0051 (8)	−0.0006 (8)	−0.0115 (9)
C9	0.0443 (12)	0.0427 (12)	0.0435 (12)	−0.0110 (10)	0.0017 (9)	−0.0175 (10)
C10	0.0494 (13)	0.0661 (16)	0.0489 (14)	−0.0139 (12)	0.0008 (10)	−0.0314 (12)
C11	0.0545 (14)	0.0778 (18)	0.0368 (13)	−0.0136 (13)	0.0003 (10)	−0.0224 (12)
C12	0.0555 (14)	0.0582 (15)	0.0368 (12)	−0.0130 (12)	0.0014 (10)	−0.0054 (11)
C13	0.0429 (12)	0.0410 (12)	0.0377 (12)	−0.0095 (9)	0.0002 (9)	−0.0109 (9)
N14	0.0648 (13)	0.0363 (10)	0.0413 (11)	−0.0213 (9)	−0.0015 (9)	−0.0049 (8)
C15	0.0532 (13)	0.0388 (12)	0.0398 (12)	−0.0147 (10)	−0.0043 (10)	−0.0115 (9)
C16	0.0558 (13)	0.0381 (12)	0.0395 (12)	−0.0119 (10)	−0.0126 (10)	−0.0092 (9)
N17	0.0899 (17)	0.0533 (13)	0.0592 (14)	−0.0350 (12)	−0.0293 (12)	−0.0053 (10)
C18	0.0427 (11)	0.0357 (11)	0.0320 (11)	−0.0119 (9)	−0.0076 (8)	−0.0054 (8)
C19	0.0463 (12)	0.0546 (14)	0.0384 (12)	−0.0064 (10)	−0.0130 (10)	−0.0138 (10)
C20	0.0632 (16)	0.0678 (16)	0.0349 (12)	−0.0037 (13)	−0.0084 (11)	−0.0195 (11)
C21	0.0511 (14)	0.0557 (15)	0.0375 (13)	−0.0017 (11)	0.0017 (10)	−0.0040 (11)
C22	0.0407 (12)	0.0694 (17)	0.0472 (14)	−0.0072 (11)	−0.0095 (10)	−0.0094 (12)
C23	0.0466 (13)	0.0585 (14)	0.0413 (12)	−0.0136 (11)	−0.0109 (10)	−0.0137 (11)
C24	0.0368 (11)	0.0352 (11)	0.0431 (12)	−0.0078 (9)	−0.0011 (9)	−0.0129 (9)
C25	0.0737 (17)	0.0415 (13)	0.0481 (14)	−0.0196 (12)	−0.0043 (12)	−0.0095 (11)
C26	0.0767 (18)	0.0367 (13)	0.0698 (18)	−0.0200 (12)	−0.0008 (14)	−0.0111 (12)
C27	0.0606 (16)	0.0446 (14)	0.0786 (19)	−0.0162 (12)	−0.0004 (13)	−0.0313 (13)
C28	0.0643 (16)	0.0558 (15)	0.0594 (16)	−0.0184 (12)	−0.0043 (12)	−0.0293 (13)
N29	0.0549 (11)	0.0451 (11)	0.0461 (11)	−0.0165 (9)	−0.0044 (9)	−0.0178 (9)

Cl1—C19	1.737 (2)	C12—H12	0.9300
Cl2—C21	1.740 (2)	C13—N14	1.372 (3)
N1—C2	1.367 (3)	N14—C15	1.345 (3)
N1—C6	1.392 (3)	N14—H14	0.84 (3)
N1—H1	0.84 (3)	C15—H15	0.9300
C2—C3	1.366 (3)	C16—N17	1.147 (3)
C2—C7	1.459 (3)	C18—C19	1.385 (3)
C3—C16	1.413 (3)	C18—C23	1.388 (3)
C3—C4	1.526 (3)	C19—C20	1.384 (3)
C4—C5	1.506 (3)	C20—C21	1.371 (4)
C4—C18	1.524 (3)	C20—H20	0.9300
C4—H4	0.9800	C21—C22	1.367 (4)
C5—C6	1.326 (3)	C22—C23	1.379 (3)
C5—H5	0.9300	C22—H22	0.9300
C6—C24	1.487 (3)	C23—H23	0.9300
C7—C15	1.377 (3)	C24—N29	1.331 (3)
C7—C8	1.456 (3)	C24—C25	1.388 (3)
C8—C9	1.407 (3)	C25—C26	1.376 (3)
C8—C13	1.413 (3)	C25—H25	0.9300
C9—C10	1.372 (3)	C26—C27	1.364 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.395 (4)	C27—C28	1.369 (4)
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.370 (4)	C28—N29	1.339 (3)
C11—H11	0.9300	C28—H28	0.9300
C12—C13	1.389 (3)
C2—N1—C6	122.28 (18)	C15—N14—C13	109.48 (19)
C2—N1—H1	120.3 (19)	C15—N14—H14	124.8 (17)
C6—N1—H1	115.6 (19)	C13—N14—H14	125.8 (17)
C3—C2—N1	117.87 (18)	N14—C15—C7	110.8 (2)
C3—C2—C7	125.98 (18)	N14—C15—H15	124.6
N1—C2—C7	116.15 (18)	C7—C15—H15	124.6
C2—C3—C16	122.62 (19)	N17—C16—C3	174.7 (2)
C2—C3—C4	122.64 (17)	C19—C18—C23	116.2 (2)
C16—C3—C4	114.67 (18)	C19—C18—C4	123.25 (19)
C5—C4—C18	111.94 (17)	C23—C18—C4	120.57 (19)
C5—C4—C3	108.98 (16)	C20—C19—C18	122.5 (2)
C18—C4—C3	112.45 (17)	C20—C19—Cl1	116.87 (17)
C5—C4—H4	107.8	C18—C19—Cl1	120.65 (18)
C18—C4—H4	107.8	C21—C20—C19	118.6 (2)
C3—C4—H4	107.8	C21—C20—H20	120.7
C6—C5—C4	122.38 (19)	C19—C20—H20	120.7
C6—C5—H5	118.8	C22—C21—C20	121.4 (2)
C4—C5—H5	118.8	C22—C21—Cl2	119.8 (2)
C5—C6—N1	120.15 (18)	C20—C21—Cl2	118.7 (2)
C5—C6—C24	125.28 (19)	C21—C22—C23	118.6 (2)
N1—C6—C24	114.49 (18)	C21—C22—H22	120.7
C15—C7—C8	105.65 (18)	C23—C22—H22	120.7
C15—C7—C2	125.51 (19)	C22—C23—C18	122.7 (2)
C8—C7—C2	128.75 (18)	C22—C23—H23	118.6
C9—C8—C13	117.36 (19)	C18—C23—H23	118.6
C9—C8—C7	136.58 (19)	N29—C24—C25	122.0 (2)
C13—C8—C7	106.06 (18)	N29—C24—C6	115.44 (18)
C10—C9—C8	119.2 (2)	C25—C24—C6	122.6 (2)
C10—C9—H9	120.4	C26—C25—C24	119.1 (2)
C8—C9—H9	120.4	C26—C25—H25	120.4
C9—C10—C11	121.7 (2)	C24—C25—H25	120.4
C9—C10—H10	119.1	C27—C26—C25	119.2 (2)
C11—C10—H10	119.1	C27—C26—H26	120.4
C12—C11—C10	121.0 (2)	C25—C26—H26	120.4
C12—C11—H11	119.5	C26—C27—C28	118.2 (2)
C10—C11—H11	119.5	C26—C27—H27	120.9
C11—C12—C13	117.3 (2)	C28—C27—H27	120.9
C11—C12—H12	121.3	N29—C28—C27	123.9 (2)
C13—C12—H12	121.3	N29—C28—H28	118.0
N14—C13—C12	128.7 (2)	C27—C28—H28	118.0
N14—C13—C8	107.98 (19)	C24—N29—C28	117.5 (2)
C12—C13—C8	123.3 (2)
C6—N1—C2—C3	15.0 (3)	C8—C13—N14—C15	0.3 (3)
C6—N1—C2—C7	−164.76 (19)	C13—N14—C15—C7	−0.2 (3)
N1—C2—C3—C16	−170.6 (2)	C8—C7—C15—N14	0.0 (3)
C7—C2—C3—C16	9.1 (3)	C2—C7—C15—N14	176.8 (2)
N1—C2—C3—C4	6.2 (3)	C2—C3—C16—N17	173 (3)
C7—C2—C3—C4	−174.09 (19)	C4—C3—C16—N17	−4(3)
C2—C3—C4—C5	−22.1 (3)	C5—C4—C18—C19	−126.6 (2)
C16—C3—C4—C5	154.91 (19)	C3—C4—C18—C19	110.4 (2)
C2—C3—C4—C18	102.6 (2)	C5—C4—C18—C23	52.5 (3)
C16—C3—C4—C18	−80.4 (2)	C3—C4—C18—C23	−70.6 (2)
C18—C4—C5—C6	−104.9 (2)	C23—C18—C19—C20	−1.6 (3)
C3—C4—C5—C6	20.1 (3)	C4—C18—C19—C20	177.5 (2)
C4—C5—C6—N1	−2.5 (3)	C23—C18—C19—Cl1	178.79 (17)
C4—C5—C6—C24	−179.03 (19)	C4—C18—C19—Cl1	−2.1 (3)
C2—N1—C6—C5	−17.2 (3)	C18—C19—C20—C21	0.7 (4)
C2—N1—C6—C24	159.66 (19)	Cl1—C19—C20—C21	−179.7 (2)
C3—C2—C7—C15	19.2 (3)	C19—C20—C21—C22	0.7 (4)
N1—C2—C7—C15	−161.1 (2)	C19—C20—C21—Cl2	−178.27 (19)
C3—C2—C7—C8	−164.7 (2)	C20—C21—C22—C23	−1.1 (4)
N1—C2—C7—C8	15.0 (3)	Cl2—C21—C22—C23	177.89 (19)
C15—C7—C8—C9	180.0 (2)	C21—C22—C23—C18	0.1 (4)
C2—C7—C8—C9	3.3 (4)	C19—C18—C23—C22	1.2 (3)
C15—C7—C8—C13	0.2 (2)	C4—C18—C23—C22	−177.9 (2)
C2—C7—C8—C13	−176.5 (2)	C5—C6—C24—N29	172.5 (2)
C13—C8—C9—C10	1.2 (3)	N1—C6—C24—N29	−4.2 (3)
C7—C8—C9—C10	−178.6 (2)	C5—C6—C24—C25	−7.3 (4)
C8—C9—C10—C11	−0.6 (4)	N1—C6—C24—C25	176.0 (2)
C9—C10—C11—C12	−0.8 (4)	N29—C24—C25—C26	−0.8 (4)
C10—C11—C12—C13	1.4 (4)	C6—C24—C25—C26	179.0 (2)
C11—C12—C13—N14	178.8 (2)	C24—C25—C26—C27	0.0 (4)
C11—C12—C13—C8	−0.7 (4)	C25—C26—C27—C28	0.5 (4)
C9—C8—C13—N14	179.84 (19)	C26—C27—C28—N29	−0.2 (4)
C7—C8—C13—N14	−0.3 (2)	C25—C24—N29—C28	1.1 (3)
C9—C8—C13—C12	−0.6 (3)	C6—C24—N29—C28	−178.8 (2)
C7—C8—C13—C12	179.3 (2)	C27—C28—N29—C24	−0.6 (4)
C12—C13—N14—C15	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N29	0.85 (3)	2.21 (3)	2.638 (2)	111 (2)
C4—H4···Cl1	0.98	2.56	3.114 (2)	116.
N14—H14···N17i	0.84 (3)	2.14 (3)	2.937 (3)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N29	0.85 (3)	2.21 (3)	2.638 (2)	111 (2)
C4—H4⋯Cl1	0.98	2.56	3.114 (2)	116
N14—H14⋯N17i	0.84 (3)	2.14 (3)	2.937 (3)	158 (2)

Symmetry code: (i) .