4-(4-Bromo-phen-yl)-6-(1H-indol-3-yl)-2,2'-bipyridine-5-carbonitrile.

In the title compound, C(25)H(15)BrN(4), the two pyridine rings lie in a common plane [r.m.s. deviation = 0.023 (2) Å], whereas the bromo-phenyl and indole rings are twisted away from this plane by 52.82 (12) and 28.02 (10)°, respectively. The crystal structure is stabilized by inter-molecular N-H⋯N inter-actions.

Related literature

Compounds having an indole ring system have been shown to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶);

Experimental

Crystal data

C25H15BrN4

M = 451.32

Orthorhombic,

a = 14.7393 (4) Å

b = 10.7465 (3) Å

c = 25.4251 (7) Å

V = 4027.23 (19) Å3

Z = 8

Mo Kα radiation

μ = 2.06 mm−1

T = 293 (2) K

0.29 × 0.26 × 0.22 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.556, T max = 0.635

47903 measured reflections

5545 independent reflections

3138 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 0.99

5545 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001354/bt2842sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001354/bt2842Isup2.hkl

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

C25H15BrN4	F(000) = 1824
Mr = 451.32	Dx = 1.489 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5842 reflections
a = 14.7393 (4) Å	θ = 1.6–29.4°
b = 10.7465 (3) Å	µ = 2.06 mm−1
c = 25.4251 (7) Å	T = 293 K
V = 4027.23 (19) Å3	Block, colorless
Z = 8	0.29 × 0.26 × 0.22 mm

Bruker Kappa APEXII area-detector diffractometer	5545 independent reflections
Radiation source: fine-focus sealed tube	3138 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω and φ scans	θmax = 29.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −17→20
Tmin = 0.556, Tmax = 0.635	k = −14→14
47903 measured reflections	l = −35→35

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0524P)2 + 1.6981P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
5545 reflections	Δρmax = 0.42 e Å−3
272 parameters	Δρmin = −0.58 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (2)

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
Br1	0.24258 (2)	0.41762 (4)	0.228490 (11)	0.07539 (16)
N1	0.40577 (13)	0.47359 (16)	0.56512 (7)	0.0397 (4)
C2	0.41263 (15)	0.3612 (2)	0.54258 (9)	0.0385 (5)
C3	0.38681 (16)	0.3440 (2)	0.48975 (9)	0.0399 (5)
C4	0.35912 (16)	0.4449 (2)	0.45926 (9)	0.0391 (5)
C5	0.35655 (16)	0.5595 (2)	0.48331 (9)	0.0426 (5)
H5	0.3406	0.6298	0.4641	0.051*
C6	0.37776 (15)	0.5701 (2)	0.53619 (9)	0.0387 (5)
C7	0.44948 (15)	0.2632 (2)	0.57570 (9)	0.0400 (5)
C8	0.44917 (15)	0.2595 (2)	0.63245 (9)	0.0402 (5)
C9	0.41165 (18)	0.3326 (2)	0.67203 (10)	0.0490 (6)
H9	0.3769	0.4021	0.6637	0.059*
C10	0.4265 (2)	0.3010 (3)	0.72342 (10)	0.0591 (7)
H10	0.4022	0.3503	0.7499	0.071*
C11	0.4771 (2)	0.1972 (3)	0.73681 (11)	0.0640 (8)
H11	0.4861	0.1783	0.7721	0.077*
C12	0.5139 (2)	0.1223 (3)	0.69920 (11)	0.0596 (7)
H12	0.5473	0.0521	0.7082	0.072*
C13	0.49973 (16)	0.1545 (2)	0.64702 (10)	0.0463 (6)
N14	0.52963 (15)	0.09858 (18)	0.60195 (9)	0.0533 (5)
H14	0.5626	0.0327	0.6007	0.064*
C15	0.49954 (16)	0.1625 (2)	0.55983 (10)	0.0485 (6)
H15	0.5111	0.1413	0.5250	0.058*
C16	0.38817 (18)	0.2223 (2)	0.46641 (10)	0.0480 (6)
N17	0.38837 (19)	0.1271 (2)	0.44684 (10)	0.0694 (7)
C18	0.33250 (16)	0.4340 (2)	0.40326 (9)	0.0403 (5)
C19	0.26769 (17)	0.3498 (2)	0.38682 (10)	0.0504 (6)
H19	0.2413	0.2960	0.4110	0.060*
C20	0.24170 (18)	0.3450 (2)	0.33465 (11)	0.0530 (7)
H20	0.1982	0.2879	0.3237	0.064*
C21	0.28003 (18)	0.4241 (2)	0.29947 (10)	0.0481 (6)
C22	0.34485 (19)	0.5078 (3)	0.31444 (10)	0.0562 (7)
H22	0.3712	0.5608	0.2899	0.067*
C23	0.37058 (19)	0.5126 (2)	0.36651 (10)	0.0523 (6)
H23	0.4143	0.5697	0.3770	0.063*
C24	0.36885 (16)	0.6912 (2)	0.56355 (9)	0.0410 (5)
N25	0.33924 (15)	0.78608 (18)	0.53415 (8)	0.0516 (5)
C26	0.32987 (19)	0.8957 (2)	0.55752 (12)	0.0562 (7)
H26	0.3101	0.9624	0.5373	0.067*
C27	0.3474 (2)	0.9165 (2)	0.60946 (12)	0.0595 (7)
H27	0.3388	0.9947	0.6243	0.071*
C28	0.3779 (3)	0.8194 (3)	0.63905 (12)	0.0756 (9)
H28	0.3908	0.8304	0.6746	0.091*
C29	0.3895 (2)	0.7051 (2)	0.61584 (10)	0.0624 (8)
H29	0.4110	0.6381	0.6353	0.075*

	U11	U22	U33	U12	U13	U23
Br1	0.0741 (2)	0.1126 (3)	0.03942 (16)	0.02193 (18)	−0.00909 (13)	0.00200 (15)
N1	0.0451 (11)	0.0356 (10)	0.0385 (10)	0.0036 (8)	0.0000 (8)	0.0014 (8)
C2	0.0390 (13)	0.0360 (12)	0.0403 (12)	0.0018 (9)	0.0016 (10)	0.0024 (10)
C3	0.0419 (13)	0.0357 (12)	0.0420 (13)	0.0005 (10)	0.0031 (10)	−0.0014 (10)
C4	0.0422 (13)	0.0380 (12)	0.0370 (12)	0.0002 (10)	0.0033 (10)	0.0030 (10)
C5	0.0528 (14)	0.0342 (12)	0.0408 (13)	0.0033 (10)	−0.0002 (10)	0.0050 (10)
C6	0.0411 (12)	0.0357 (11)	0.0395 (12)	0.0005 (9)	0.0029 (10)	0.0020 (10)
C7	0.0410 (13)	0.0346 (11)	0.0444 (13)	0.0009 (10)	−0.0015 (10)	0.0008 (10)
C8	0.0428 (13)	0.0337 (11)	0.0442 (13)	−0.0045 (10)	−0.0066 (10)	0.0054 (10)
C9	0.0578 (16)	0.0416 (13)	0.0477 (14)	−0.0040 (12)	0.0001 (12)	0.0020 (11)
C10	0.0737 (19)	0.0608 (17)	0.0427 (15)	−0.0128 (14)	−0.0027 (13)	0.0005 (12)
C11	0.074 (2)	0.0704 (19)	0.0475 (15)	−0.0201 (16)	−0.0152 (14)	0.0149 (14)
C12	0.0648 (18)	0.0527 (15)	0.0613 (17)	−0.0053 (13)	−0.0194 (14)	0.0189 (14)
C13	0.0463 (14)	0.0390 (13)	0.0537 (15)	−0.0028 (10)	−0.0091 (12)	0.0059 (11)
N14	0.0550 (13)	0.0400 (11)	0.0648 (14)	0.0130 (10)	−0.0099 (11)	0.0043 (10)
C15	0.0511 (15)	0.0430 (13)	0.0513 (14)	0.0073 (11)	−0.0027 (12)	−0.0010 (11)
C16	0.0553 (15)	0.0438 (14)	0.0450 (14)	0.0084 (11)	−0.0056 (11)	−0.0008 (11)
N17	0.0931 (19)	0.0476 (13)	0.0675 (16)	0.0163 (12)	−0.0173 (14)	−0.0139 (12)
C18	0.0479 (14)	0.0375 (12)	0.0354 (11)	0.0036 (10)	0.0013 (10)	0.0011 (10)
C19	0.0563 (16)	0.0490 (14)	0.0458 (14)	−0.0095 (12)	−0.0059 (12)	0.0126 (11)
C20	0.0556 (16)	0.0533 (15)	0.0502 (15)	−0.0060 (12)	−0.0131 (12)	0.0009 (12)
C21	0.0544 (15)	0.0538 (14)	0.0360 (12)	0.0118 (13)	−0.0038 (11)	0.0011 (11)
C22	0.0705 (18)	0.0571 (16)	0.0412 (14)	−0.0020 (14)	0.0107 (13)	0.0090 (12)
C23	0.0626 (17)	0.0472 (14)	0.0472 (14)	−0.0133 (12)	0.0042 (12)	0.0015 (12)
C24	0.0433 (13)	0.0354 (12)	0.0442 (13)	0.0003 (10)	0.0044 (10)	0.0021 (10)
N25	0.0663 (14)	0.0373 (10)	0.0511 (13)	0.0095 (10)	−0.0024 (11)	−0.0019 (9)
C26	0.0650 (18)	0.0387 (13)	0.0648 (18)	0.0103 (12)	0.0007 (14)	0.0007 (12)
C27	0.0716 (18)	0.0421 (14)	0.0647 (18)	0.0018 (13)	0.0102 (14)	−0.0117 (13)
C28	0.122 (3)	0.0565 (18)	0.0484 (17)	0.0025 (18)	−0.0037 (17)	−0.0114 (14)
C29	0.099 (2)	0.0438 (14)	0.0446 (15)	0.0048 (14)	−0.0079 (15)	0.0001 (12)

Br1—C21	1.888 (2)	N14—C15	1.347 (3)
N1—C6	1.336 (3)	N14—H14	0.8600
N1—C2	1.341 (3)	C15—H15	0.9300
C2—C3	1.408 (3)	C16—N17	1.138 (3)
C2—C7	1.453 (3)	C18—C23	1.379 (3)
C3—C4	1.394 (3)	C18—C19	1.381 (3)
C3—C16	1.437 (3)	C19—C20	1.382 (3)
C4—C5	1.376 (3)	C19—H19	0.9300
C4—C18	1.482 (3)	C20—C21	1.357 (4)
C5—C6	1.385 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.367 (4)
C6—C24	1.481 (3)	C22—C23	1.378 (3)
C7—C15	1.371 (3)	C22—H22	0.9300
C7—C8	1.443 (3)	C23—H23	0.9300
C8—C9	1.391 (3)	C24—N25	1.338 (3)
C8—C13	1.403 (3)	C24—C29	1.372 (3)
C9—C10	1.368 (3)	N25—C26	1.327 (3)
C9—H9	0.9300	C26—C27	1.364 (4)
C10—C11	1.383 (4)	C26—H26	0.9300
C10—H10	0.9300	C27—C28	1.363 (4)
C11—C12	1.363 (4)	C27—H27	0.9300
C11—H11	0.9300	C28—C29	1.373 (4)
C12—C13	1.387 (3)	C28—H28	0.9300
C12—H12	0.9300	C29—H29	0.9300
C13—N14	1.367 (3)
C6—N1—C2	119.15 (19)	C13—N14—H14	125.2
N1—C2—C3	120.32 (19)	N14—C15—C7	110.2 (2)
N1—C2—C7	115.66 (19)	N14—C15—H15	124.9
C3—C2—C7	124.0 (2)	C7—C15—H15	124.9
C4—C3—C2	120.5 (2)	N17—C16—C3	178.4 (3)
C4—C3—C16	118.8 (2)	C23—C18—C19	118.5 (2)
C2—C3—C16	120.6 (2)	C23—C18—C4	119.7 (2)
C5—C4—C3	117.2 (2)	C19—C18—C4	121.7 (2)
C5—C4—C18	119.4 (2)	C18—C19—C20	120.5 (2)
C3—C4—C18	123.4 (2)	C18—C19—H19	119.8
C4—C5—C6	119.9 (2)	C20—C19—H19	119.8
C4—C5—H5	120.0	C21—C20—C19	119.6 (2)
C6—C5—H5	120.0	C21—C20—H20	120.2
N1—C6—C5	122.7 (2)	C19—C20—H20	120.2
N1—C6—C24	116.8 (2)	C20—C21—C22	121.3 (2)
C5—C6—C24	120.5 (2)	C20—C21—Br1	119.0 (2)
C15—C7—C8	105.9 (2)	C22—C21—Br1	119.64 (19)
C15—C7—C2	127.0 (2)	C21—C22—C23	119.0 (2)
C8—C7—C2	126.7 (2)	C21—C22—H22	120.5
C9—C8—C13	118.3 (2)	C23—C22—H22	120.5
C9—C8—C7	135.1 (2)	C22—C23—C18	121.1 (2)
C13—C8—C7	106.5 (2)	C22—C23—H23	119.5
C10—C9—C8	119.1 (2)	C18—C23—H23	119.5
C10—C9—H9	120.4	N25—C24—C29	122.0 (2)
C8—C9—H9	120.4	N25—C24—C6	115.9 (2)
C9—C10—C11	121.4 (3)	C29—C24—C6	122.1 (2)
C9—C10—H10	119.3	C26—N25—C24	117.4 (2)
C11—C10—H10	119.3	N25—C26—C27	124.0 (2)
C12—C11—C10	121.2 (3)	N25—C26—H26	118.0
C12—C11—H11	119.4	C27—C26—H26	118.0
C10—C11—H11	119.4	C28—C27—C26	118.1 (2)
C11—C12—C13	117.6 (3)	C28—C27—H27	120.9
C11—C12—H12	121.2	C26—C27—H27	120.9
C13—C12—H12	121.2	C27—C28—C29	119.2 (3)
N14—C13—C12	130.1 (2)	C27—C28—H28	120.4
N14—C13—C8	107.7 (2)	C29—C28—H28	120.4
C12—C13—C8	122.2 (2)	C24—C29—C28	119.1 (3)
C15—N14—C13	109.6 (2)	C24—C29—H29	120.4
C15—N14—H14	125.2	C28—C29—H29	120.4
C6—N1—C2—C3	−2.8 (3)	C7—C8—C13—C12	179.7 (2)
C6—N1—C2—C7	175.9 (2)	C12—C13—N14—C15	−179.7 (3)
N1—C2—C3—C4	4.0 (3)	C8—C13—N14—C15	−0.7 (3)
C7—C2—C3—C4	−174.6 (2)	C13—N14—C15—C7	0.5 (3)
N1—C2—C3—C16	−175.8 (2)	C8—C7—C15—N14	−0.2 (3)
C7—C2—C3—C16	5.6 (4)	C2—C7—C15—N14	173.8 (2)
C2—C3—C4—C5	−1.3 (3)	C4—C3—C16—N17	−4(11)
C16—C3—C4—C5	178.4 (2)	C2—C3—C16—N17	176 (100)
C2—C3—C4—C18	179.0 (2)	C5—C4—C18—C23	50.8 (3)
C16—C3—C4—C18	−1.3 (3)	C3—C4—C18—C23	−129.5 (3)
C3—C4—C5—C6	−2.3 (3)	C5—C4—C18—C19	−126.8 (3)
C18—C4—C5—C6	177.4 (2)	C3—C4—C18—C19	52.9 (3)
C2—N1—C6—C5	−1.0 (3)	C23—C18—C19—C20	−0.1 (4)
C2—N1—C6—C24	178.2 (2)	C4—C18—C19—C20	177.5 (2)
C4—C5—C6—N1	3.6 (4)	C18—C19—C20—C21	−0.3 (4)
C4—C5—C6—C24	−175.5 (2)	C19—C20—C21—C22	0.8 (4)
N1—C2—C7—C15	−149.1 (2)	C19—C20—C21—Br1	−179.2 (2)
C3—C2—C7—C15	29.6 (4)	C20—C21—C22—C23	−0.8 (4)
N1—C2—C7—C8	23.7 (3)	Br1—C21—C22—C23	179.1 (2)
C3—C2—C7—C8	−157.7 (2)	C21—C22—C23—C18	0.4 (4)
C15—C7—C8—C9	−179.9 (3)	C19—C18—C23—C22	0.0 (4)
C2—C7—C8—C9	6.1 (4)	C4—C18—C23—C22	−177.7 (2)
C15—C7—C8—C13	−0.3 (3)	N1—C6—C24—N25	−178.9 (2)
C2—C7—C8—C13	−174.2 (2)	C5—C6—C24—N25	0.3 (3)
C13—C8—C9—C10	1.1 (4)	N1—C6—C24—C29	1.0 (4)
C7—C8—C9—C10	−179.3 (3)	C5—C6—C24—C29	−179.8 (3)
C8—C9—C10—C11	−0.8 (4)	C29—C24—N25—C26	−0.3 (4)
C9—C10—C11—C12	−0.1 (4)	C6—C24—N25—C26	179.5 (2)
C10—C11—C12—C13	0.7 (4)	C24—N25—C26—C27	−0.9 (4)
C11—C12—C13—N14	178.6 (3)	N25—C26—C27—C28	1.2 (5)
C11—C12—C13—C8	−0.3 (4)	C26—C27—C28—C29	−0.2 (5)
C9—C8—C13—N14	−179.7 (2)	N25—C24—C29—C28	1.2 (4)
C7—C8—C13—N14	0.6 (3)	C6—C24—C29—C28	−178.7 (3)
C9—C8—C13—C12	−0.6 (4)	C27—C28—C29—C24	−0.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···N17i	0.86	2.22	2.980 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14⋯N17i	0.86	2.22	2.980 (3)	147

Symmetry code: (i) .