4-(4-Bromo­phen­yl)-6-(1H-indol-3-yl)-2,2′-bipyridine-5-carbonitrile

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

doi:10.1107/S1600536809001354

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o450

doi:10.1107/S1600536809001354

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4-(4-Bromophenyl)-6-(1H-indol-3-yl)-2,2′-bipyridine-5-carbonitrile

P. Ramesh,^a A. Subbiahpandi,^a P. Thirumurugan,^b Paramasivan 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 20 December 2008; accepted 12 January 2009; online 4 February 2009)

In the title compound, C₂₅H₁₅BrN₄, the two pyridine rings lie in a common plane [r.m.s. deviation = 0.023 (2) Å], whereas the bromophenyl and indole rings are twisted away from this plane by 52.82 (12) and 28.02 (10)°, respectively. The crystal structure is stabilized by intermolecular N—H⋯N interactions.

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_r = 451.32
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.120
S = 0.99
5545 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.58 e Å⁻³

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

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 ).

Supporting information

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

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

checkCIF report

Comment top

Compounds having indole ring system are proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). Against this background and to ascertain the detailed conformation, the crystal structure determination of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig. 1. The two pyridine rings lie in the same plane as can be seen from the dihedral angle of 3.61 (13)°. The bromophenyl and indole rings are twisted away from the bipyridine ring by 52.82 (12)° and 28.02 (10)°, respectively. The sum of the bond angles at N14 (360.0°) in the indole ring is in accordance with sp² hybridization. The bond angle of C3—C16—N17 [178.4 (3)°] shows the linearity of the cyano group, a feature observed in carbonitrile compounds.

The crystal packing is controlled by C—H···N intermolecular interactions in addition to van der Waals forces. Atom N14 (x, y, z) donates one proton to N17 at (-x + 1,-y,-z + 1) which connects the molecules to form a R₂² (16) dimer (Bernstein et al., 1995).

Related literature top

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 top

A mixture of 3-cyanoacetyl indole (1 mmol), 4-bromobenzaldehyde (1 mmol) and 2-acetyl pyridine (1 mmol) in 5 gm of ammonium acetate under neat condition was refluxed 6–8 hrs. 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 80% yield (90:10, petroleum ether: ethyl acetate) and recrystallized in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (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. Perspective view of the molecule showing the displacement ellipsoids at 50% probability level. The H atoms are shown as small circles of arbitrary radii.
	Fig. 2. The crystal packing of the molecules viewed down the b axis. H atoms not involved in hydrogen bonding are omitted for clarity.

4-(4-Bromophenyl)-6-(1H-indol-3-yl)-2,2'-bipyridine-5-carbonitrile top

Crystal data top

C₂₅H₁₅BrN₄	F(000) = 1824
M_r = 451.32	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0524P)² + 1.6981P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
5545 reflections	Δρ_max = 0.42 e Å⁻³
272 parameters	Δρ_min = −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)

Crystal data top

C₂₅H₁₅BrN₄	V = 4027.23 (19) Å³
M_r = 451.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.7393 (4) Å	µ = 2.06 mm⁻¹
b = 10.7465 (3) Å	T = 293 K
c = 25.4251 (7) Å	0.29 × 0.26 × 0.22 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	5545 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3138 reflections with I > 2σ(I)
T_min = 0.556, T_max = 0.635	R_int = 0.057
47903 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 0.99	Δρ_max = 0.42 e Å⁻³
5545 reflections	Δρ_min = −0.58 e Å⁻³
272 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₅BrN₄
M_r	451.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	14.7393 (4), 10.7465 (3), 25.4251 (7)
V (Å³)	4027.23 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.06
Crystal size (mm)	0.29 × 0.26 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.556, 0.635
No. of measured, independent and observed [I > 2σ(I)] reflections	47903, 5545, 3138
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.691

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 0.99
No. of reflections	5545
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.58

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
N14—H14···N17ⁱ	0.86	2.22	2.980 (3)	147.3

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

PR thanks Dr Babu Varghese, SAIF, IIT–Madras, India, for his help with the data collection.

References

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