6-Bromo-pyridine-2-carbaldehyde phenyl-hydrazone.

The title compound, C(12)H(10)BrN(3), is essentially planar (r.m.s. deviation of all non-H atoms = 0.0174 Å), with a dihedral angle of 0.5 (2)° between the two aromatic rings. In the crystal, mol-ecules are linked by weak N-H⋯N inter-actions, forming a zigzag chain running parallel to [001].

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Yu et al. (2005 ▶); Fun et al. (2012 ▶). For the design of mol­ecular dynamic systems, see: Hirose (2010 ▶). For the principles of synthetic mol­ecular structures with dynamic properties, see: Kay et al. (2007 ▶). For configurational changes by UV light and heat, see: Chaur et al. (2011 ▶); Lehn (2006 ▶); Dugave & Demange (2003 ▶). For graph-set notation, see: Etter (1990 ▶).

Experimental

Crystal data

C12H10BrN3

M = 276.13

Orthorhombic,

a = 14.6418 (3) Å

b = 7.8407 (1) Å

c = 20.0645 (4) Å

V = 2303.44 (7) Å3

Z = 8

Mo Kα radiation

μ = 3.54 mm−1

T = 295 K

0.33 × 0.30 × 0.23 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.382, T max = 0.544

28166 measured reflections

2339 independent reflections

1903 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.03

2339 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.72 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812026517/gg2083sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026517/gg2083Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026517/gg2083Isup3.cml

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

C12H10BrN3	Dx = 1.593 Mg m−3
Mr = 276.13	Melting point: 497(1) K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9233 reflections
a = 14.6418 (3) Å	θ = 3.6–26.4°
b = 7.8407 (1) Å	µ = 3.54 mm−1
c = 20.0645 (4) Å	T = 295 K
V = 2303.44 (7) Å3	Block, black
Z = 8	0.33 × 0.30 × 0.23 mm
F(000) = 1104

Nonius KappaCCD diffractometer	2339 independent reflections
Radiation source: fine-focus sealed tube	1903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
CCD rotation images, thick slices scans	θmax = 26.4°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→17
Tmin = 0.382, Tmax = 0.544	k = −9→9
28166 measured reflections	l = −24→25

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.052P)2 + 1.6466P] where P = (Fo2 + 2Fc2)/3
2339 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.82948 (2)	1.00944 (4)	0.314727 (18)	0.07300 (18)
N1	1.06677 (16)	0.1846 (3)	0.32501 (10)	0.0535 (5)
H1	1.0780	0.2044	0.2837	0.064*
N2	1.01869 (15)	0.2984 (3)	0.36079 (10)	0.0506 (5)
N3	0.91170 (14)	0.6977 (3)	0.33261 (10)	0.0468 (5)
C1	0.86323 (18)	0.8132 (3)	0.36454 (13)	0.0496 (6)
C2	0.8363 (2)	0.8049 (4)	0.43023 (14)	0.0620 (7)
H2	0.8017	0.8907	0.4499	0.074*
C3	0.8635 (2)	0.6620 (4)	0.46526 (14)	0.0674 (8)
H3	0.8471	0.6495	0.5098	0.081*
C4	0.9144 (2)	0.5390 (4)	0.43455 (13)	0.0577 (7)
H4	0.9332	0.4428	0.4579	0.069*
C5	0.93799 (17)	0.5597 (3)	0.36750 (12)	0.0467 (5)
C7	0.99160 (18)	0.4341 (4)	0.33110 (12)	0.0506 (6)
H7	1.0061	0.4522	0.2865	0.061*
C8	1.09823 (17)	0.0360 (3)	0.35418 (12)	0.0460 (5)
C9	1.0819 (2)	−0.0034 (3)	0.42067 (14)	0.0568 (7)
H9	1.0468	0.0692	0.4469	0.068*
C10	1.1179 (2)	−0.1504 (4)	0.44746 (15)	0.0696 (8)
H10	1.1073	−0.1750	0.4921	0.084*
C11	1.1688 (2)	−0.2614 (4)	0.41011 (18)	0.0704 (8)
H11	1.1925	−0.3603	0.4289	0.084*
C12	1.1841 (2)	−0.2232 (4)	0.34413 (17)	0.0670 (8)
H12	1.2184	−0.2976	0.3181	0.080*
C13	1.14946 (19)	−0.0769 (4)	0.31608 (13)	0.0553 (7)
H13	1.1604	−0.0533	0.2714	0.066*

	U11	U22	U33	U12	U13	U23
Br1	0.0783 (3)	0.0622 (2)	0.0785 (3)	0.01901 (15)	−0.00590 (15)	0.00948 (14)
N1	0.0623 (14)	0.0528 (13)	0.0454 (11)	0.0095 (11)	0.0048 (9)	−0.0002 (10)
N2	0.0556 (12)	0.0466 (12)	0.0495 (11)	0.0035 (10)	−0.0006 (10)	−0.0039 (10)
N3	0.0477 (11)	0.0483 (12)	0.0444 (10)	−0.0002 (9)	−0.0039 (9)	−0.0015 (9)
C1	0.0487 (13)	0.0479 (14)	0.0521 (14)	0.0009 (11)	−0.0069 (11)	−0.0008 (11)
C2	0.0704 (19)	0.0600 (17)	0.0557 (16)	0.0063 (14)	0.0061 (13)	−0.0107 (13)
C3	0.088 (2)	0.0676 (19)	0.0460 (14)	0.0066 (17)	0.0106 (14)	−0.0021 (14)
C4	0.0731 (18)	0.0524 (14)	0.0475 (14)	0.0013 (14)	0.0007 (13)	0.0024 (12)
C5	0.0491 (13)	0.0472 (13)	0.0440 (13)	−0.0023 (11)	−0.0036 (10)	−0.0007 (11)
C7	0.0548 (15)	0.0530 (14)	0.0439 (12)	0.0004 (12)	−0.0016 (11)	−0.0019 (12)
C8	0.0439 (13)	0.0461 (13)	0.0479 (13)	−0.0012 (10)	−0.0028 (10)	−0.0045 (11)
C9	0.0661 (17)	0.0505 (16)	0.0539 (15)	0.0015 (12)	0.0063 (13)	−0.0007 (11)
C10	0.091 (2)	0.0568 (17)	0.0607 (17)	0.0001 (16)	0.0024 (16)	0.0107 (14)
C11	0.077 (2)	0.0480 (16)	0.086 (2)	0.0088 (14)	−0.0138 (16)	0.0051 (15)
C12	0.0624 (17)	0.0590 (18)	0.080 (2)	0.0144 (14)	−0.0061 (15)	−0.0181 (16)
C13	0.0539 (15)	0.0590 (17)	0.0530 (15)	0.0080 (13)	−0.0020 (12)	−0.0096 (12)

Br1—C1	1.900 (3)	C5—C7	1.455 (4)
N1—C8	1.383 (3)	C7—H7	0.9300
N1—H1	0.8600	C8—C13	1.389 (4)
N2—C7	1.282 (3)	C8—C9	1.390 (4)
N2—N1	1.344 (3)	C9—C10	1.376 (4)
N3—C1	1.317 (3)	C9—H9	0.9300
N3—C5	1.345 (3)	C10—C11	1.369 (4)
C1—C2	1.377 (4)	C10—H10	0.9300
C2—C3	1.381 (4)	C11—C12	1.375 (5)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.366 (4)	C12—C13	1.375 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.398 (4)	C13—H13	0.9300
C4—H4	0.9300
C7—N2—N1	117.7 (2)	N2—C7—H7	120.2
N2—N1—C8	120.5 (2)	C5—C7—H7	120.2
N2—N1—H1	119.7	N1—C8—C13	118.9 (2)
C8—N1—H1	119.7	N1—C8—C9	122.4 (2)
C1—N3—C5	117.0 (2)	C13—C8—C9	118.7 (3)
N3—C1—C2	125.9 (3)	C10—C9—C8	119.7 (3)
N3—C1—Br1	116.18 (19)	C10—C9—H9	120.2
C2—C1—Br1	117.9 (2)	C8—C9—H9	120.2
C1—C2—C3	116.3 (3)	C11—C10—C9	121.8 (3)
C1—C2—H2	121.8	C11—C10—H10	119.1
C3—C2—H2	121.8	C9—C10—H10	119.1
C4—C3—C2	120.0 (3)	C10—C11—C12	118.5 (3)
C4—C3—H3	120.0	C10—C11—H11	120.7
C2—C3—H3	120.0	C12—C11—H11	120.7
C3—C4—C5	119.1 (3)	C13—C12—C11	121.0 (3)
C3—C4—H4	120.4	C13—C12—H12	119.5
C5—C4—H4	120.4	C11—C12—H12	119.5
N3—C5—C4	121.5 (2)	C12—C13—C8	120.4 (3)
N3—C5—C7	115.9 (2)	C12—C13—H13	119.8
C4—C5—C7	122.5 (2)	C8—C13—H13	119.8
N2—C7—C5	119.7 (2)
C7—N2—N1—C8	179.8 (2)	N3—C5—C7—N2	−179.5 (2)
C5—N3—C1—C2	−0.6 (4)	C4—C5—C7—N2	0.2 (4)
C5—N3—C1—Br1	178.54 (17)	N2—N1—C8—C13	−178.5 (2)
N3—C1—C2—C3	0.3 (4)	N2—N1—C8—C9	0.3 (4)
Br1—C1—C2—C3	−178.8 (2)	N1—C8—C9—C10	−177.6 (3)
C1—C2—C3—C4	0.2 (5)	C13—C8—C9—C10	1.2 (4)
C2—C3—C4—C5	−0.3 (5)	C8—C9—C10—C11	−0.9 (5)
C1—N3—C5—C4	0.4 (4)	C9—C10—C11—C12	0.2 (5)
C1—N3—C5—C7	−179.9 (2)	C10—C11—C12—C13	0.2 (5)
C3—C4—C5—N3	0.0 (4)	C11—C12—C13—C8	0.1 (5)
C3—C4—C5—C7	−179.6 (3)	N1—C8—C13—C12	178.0 (3)
N1—N2—C7—C5	179.0 (2)	C9—C8—C13—C12	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.86	2.34	3.180 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.86	2.34	3.180 (3)	166

Symmetry code: (i) .