Pyridine-4-carbaldehyde 4-phenylsemicarbazone.

In the title compound, C(13)H(12)N(4)O, the semicarbazone fragment links a benzene and a pyridine ring in the structure. The crystal packing is stabilized by strong inter-molecular N-H⋯O hydrogen bonds, which connect two mol-ecules to form a synthon unit, and by N-H⋯N hydrogen bonds and weak C-H⋯π inter-actions. The mol-ecular conformation is stabil-ized by intra-molecular N-H⋯N and C-H⋯O inter-actions.

Related literature

For related compounds and their biological activity, see: Pavan et al. (2010 ▶); Yogeeswari et al. (2005 ▶).

Experimental

Crystal data

C13H12N4O

M = 240.27

Monoclinic,

a = 9.2794 (6) Å

b = 10.3384 (8) Å

c = 12.8244 (8) Å

β = 100.744 (6)°

V = 1208.73 (15) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 295 K

0.30 × 0.11 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Gemini R diffractometer

Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.888, T max = 1.000

7257 measured reflections

2310 independent reflections

1702 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.143

S = 1.06

2310 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶), PLATON (Spek, 2009) ▶ and PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013134/fy2007sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013134/fy2007Isup2.hkl

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

C13H12N4O	F(000) = 504
Mr = 240.27	Dx = 1.320 Mg m−3
Monoclinic, P21/c	Melting point: 493.15 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54180 Å
a = 9.2794 (6) Å	Cell parameters from 2114 reflections
b = 10.3384 (8) Å	θ = 3.5–70.7°
c = 12.8244 (8) Å	µ = 0.72 mm−1
β = 100.744 (6)°	T = 295 K
V = 1208.73 (15) Å3	Rod, white
Z = 4	0.30 × 0.11 × 0.06 mm

Oxford Diffraction Xcalibur Gemini R diffractometer	2310 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1702 reflections with I > 2σ(I)
graphite	Rint = 0.066
Detector resolution: 10.2673 pixels mm-1	θmax = 70.8°, θmin = 4.9°
ω scans	h = −10→11
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→11
Tmin = 0.888, Tmax = 1.000	l = −15→15
7257 measured reflections

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.0647P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2310 reflections	Δρmax = 0.20 e Å−3
176 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (8)

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 > 2sigma(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
O1	0.31018 (14)	0.04113 (16)	0.96710 (10)	0.0562 (4)
N2	0.47959 (17)	−0.03751 (17)	0.75432 (12)	0.0474 (4)
N3	0.45910 (18)	−0.01377 (19)	0.85540 (13)	0.0524 (5)
N4	0.23363 (17)	0.07764 (18)	0.78923 (13)	0.0478 (4)
N1	0.7010 (2)	−0.1407 (2)	0.43544 (14)	0.0619 (5)
C7	0.3301 (2)	0.0358 (2)	0.87508 (14)	0.0443 (5)
C4	0.5324 (2)	−0.1475 (2)	0.55575 (16)	0.0505 (5)
H4	0.4383	−0.1666	0.5665	0.061*
C3	0.5689 (2)	−0.1643 (2)	0.45723 (16)	0.0557 (5)
H3	0.4964	−0.1940	0.4024	0.067*
C8	0.0926 (2)	0.1288 (2)	0.79070 (15)	0.0467 (5)
C5	0.6378 (2)	−0.1016 (2)	0.63847 (15)	0.0466 (5)
C9	0.0279 (2)	0.2034 (2)	0.70528 (16)	0.0551 (5)
H9	0.0782	0.2193	0.6502	0.066*
C6	0.6074 (2)	−0.0739 (2)	0.74389 (16)	0.0489 (5)
C13	0.0161 (2)	0.1054 (2)	0.87145 (16)	0.0575 (6)
H13	0.0572	0.0541	0.9289	0.069*
C10	−0.1102 (3)	0.2545 (3)	0.70086 (19)	0.0672 (7)
H10	−0.1528	0.3038	0.6425	0.081*
C2	0.8014 (2)	−0.0989 (3)	0.51620 (18)	0.0657 (6)
H2	0.8949	−0.0817	0.5034	0.079*
C1	0.7765 (2)	−0.0794 (2)	0.61736 (17)	0.0571 (6)
H1	0.8519	−0.0516	0.6709	0.069*
C12	−0.1218 (2)	0.1586 (3)	0.86654 (19)	0.0687 (7)
H12	−0.1722	0.1434	0.9216	0.082*
C11	−0.1858 (3)	0.2335 (3)	0.7820 (2)	0.0712 (7)
H11	−0.2783	0.2692	0.7796	0.085*
H6	0.686 (2)	−0.083 (2)	0.8069 (17)	0.058 (6)*
H3N	0.533 (3)	−0.031 (2)	0.9132 (19)	0.065 (7)*
H4N	0.266 (2)	0.080 (2)	0.7265 (18)	0.053 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0482 (8)	0.0824 (11)	0.0385 (7)	0.0050 (7)	0.0096 (6)	−0.0017 (7)
N2	0.0489 (9)	0.0571 (10)	0.0367 (8)	0.0029 (7)	0.0089 (7)	−0.0020 (7)
N3	0.0444 (9)	0.0765 (13)	0.0358 (8)	0.0107 (8)	0.0066 (7)	−0.0017 (8)
N4	0.0439 (9)	0.0619 (11)	0.0388 (8)	0.0066 (7)	0.0110 (7)	0.0011 (7)
N1	0.0681 (12)	0.0707 (13)	0.0507 (10)	0.0103 (9)	0.0212 (9)	0.0032 (9)
C7	0.0430 (10)	0.0525 (12)	0.0373 (10)	−0.0012 (8)	0.0076 (7)	−0.0035 (8)
C4	0.0517 (11)	0.0529 (12)	0.0482 (11)	0.0021 (9)	0.0124 (9)	−0.0005 (9)
C3	0.0614 (13)	0.0577 (14)	0.0473 (12)	0.0047 (10)	0.0081 (9)	−0.0026 (9)
C8	0.0447 (10)	0.0521 (12)	0.0437 (10)	0.0019 (8)	0.0092 (8)	−0.0038 (8)
C5	0.0484 (10)	0.0497 (12)	0.0423 (10)	0.0084 (8)	0.0103 (8)	0.0044 (8)
C9	0.0580 (12)	0.0613 (14)	0.0472 (11)	0.0101 (10)	0.0127 (9)	0.0036 (10)
C6	0.0430 (10)	0.0603 (13)	0.0428 (10)	0.0061 (9)	0.0065 (8)	0.0024 (9)
C13	0.0521 (11)	0.0751 (16)	0.0479 (11)	0.0077 (10)	0.0159 (9)	0.0106 (10)
C10	0.0679 (14)	0.0759 (17)	0.0579 (14)	0.0233 (11)	0.0116 (11)	0.0102 (11)
C2	0.0568 (13)	0.0857 (18)	0.0597 (13)	0.0021 (11)	0.0239 (11)	0.0007 (12)
C1	0.0464 (11)	0.0726 (15)	0.0530 (12)	0.0040 (10)	0.0105 (9)	−0.0012 (10)
C12	0.0568 (13)	0.0924 (19)	0.0611 (14)	0.0139 (12)	0.0219 (10)	0.0058 (13)
C11	0.0586 (14)	0.0851 (19)	0.0725 (16)	0.0239 (12)	0.0193 (12)	0.0045 (13)

O1—C7	1.229 (2)	C8—C9	1.382 (3)
N2—C6	1.275 (2)	C5—C1	1.383 (3)
N2—N3	1.367 (2)	C5—C6	1.460 (3)
N3—N2	1.367 (2)	C9—C10	1.378 (3)
N3—C7	1.368 (2)	C9—H9	0.9300
N3—H3N	0.93 (2)	C6—H6	0.99 (2)
N4—C7	1.354 (2)	C13—C12	1.384 (3)
N4—C8	1.415 (2)	C13—H13	0.9300
N4—H4N	0.91 (2)	C10—C11	1.376 (3)
N1—C3	1.329 (3)	C10—H10	0.9300
N1—C2	1.329 (3)	C2—C1	1.374 (3)
C4—C3	1.379 (3)	C2—H2	0.9300
C4—C5	1.386 (3)	C1—H1	0.9300
C4—H4	0.9300	C12—C11	1.373 (3)
C3—H3	0.9300	C12—H12	0.9300
C8—C13	1.381 (3)	C11—H11	0.9300
C6—N2—N3	116.68 (16)	C10—C9—H9	119.7
N2—N3—C7	121.56 (16)	C8—C9—H9	119.7
N2—N3—H3N	120.5 (14)	N2—C6—C5	119.94 (17)
C7—N3—H3N	117.9 (14)	N2—C6—H6	120.3 (12)
C7—N4—C8	125.56 (16)	C5—C6—H6	119.8 (12)
C7—N4—H4N	116.7 (13)	C8—C13—C12	119.8 (2)
C8—N4—H4N	117.4 (13)	C8—C13—H13	120.1
C3—N1—C2	115.80 (18)	C12—C13—H13	120.1
O1—C7—N4	124.85 (17)	C11—C10—C9	120.6 (2)
O1—C7—N3	119.15 (17)	C11—C10—H10	119.7
N4—C7—N3	115.99 (16)	C9—C10—H10	119.7
C3—C4—C5	119.03 (19)	N1—C2—C1	124.5 (2)
C3—C4—H4	120.5	N1—C2—H2	117.7
N1—C3—C4	124.3 (2)	C1—C2—H2	117.7
N1—C3—H3	117.9	C2—C1—C5	119.1 (2)
C4—C3—H3	117.9	C2—C1—H1	120.4
C13—C8—C9	118.96 (18)	C5—C1—H1	120.4
C13—C8—N4	123.37 (18)	C11—C12—C13	121.3 (2)
C9—C8—N4	117.65 (18)	C11—C12—H12	119.3
C1—C5—C4	117.19 (18)	C13—C12—H12	119.3
C1—C5—C6	119.74 (18)	C12—C11—C10	118.7 (2)
C4—C5—C6	123.05 (18)	C12—C11—H11	120.7
C10—C9—C8	120.6 (2)	C10—C11—H11	120.7
C6—N2—N3—C7	174.5 (2)	N3—N2—C6—C5	179.75 (18)
C8—N4—C7—O1	−2.8 (3)	C1—C5—C6—N2	148.6 (2)
C8—N4—C7—N3	178.13 (19)	C4—C5—C6—N2	−30.0 (3)
N2—N3—C7—O1	171.39 (19)	C9—C8—C13—C12	−1.2 (3)
N2—N3—C7—N4	−9.5 (3)	N4—C8—C13—C12	−179.6 (2)
C2—N1—C3—C4	0.3 (3)	C8—C9—C10—C11	0.7 (4)
C5—C4—C3—N1	0.8 (3)	C3—N1—C2—C1	−0.1 (4)
C7—N4—C8—C13	−21.7 (3)	N1—C2—C1—C5	−1.3 (4)
C7—N4—C8—C9	159.8 (2)	C4—C5—C1—C2	2.3 (3)
C3—C4—C5—C1	−2.1 (3)	C6—C5—C1—C2	−176.3 (2)
C3—C4—C5—C6	176.49 (19)	C8—C13—C12—C11	0.8 (4)
C13—C8—C9—C10	0.4 (3)	C13—C12—C11—C10	0.3 (4)
N4—C8—C9—C10	179.0 (2)	C9—C10—C11—C12	−1.1 (4)

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1i	0.93 (2)	1.91 (2)	2.833 (2)	172 (2)
N4—H4N···N1ii	0.91 (2)	2.24 (2)	3.122 (3)	161.8 (19)
N4—H4N···N2	0.91 (2)	2.29 (2)	2.685 (2)	105.4 (16)
C13—H13···O1	0.93	2.31	2.854 (2)	117
C1—H1···Cg2iii	0.93	2.88	3.644 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1i	0.93 (2)	1.91 (2)	2.833 (2)	172 (2)
N4—H4N⋯N1ii	0.91 (2)	2.24 (2)	3.122 (3)	161.8 (19)
N4—H4N⋯N2	0.91 (2)	2.29 (2)	2.685 (2)	105.4 (16)
C13—H13⋯O1	0.93	2.31	2.854 (2)	117
C1—H1⋯Cg2iii	0.93	2.88	3.644 (2)	140

Symmetry codes: (i) ; (ii) ; (iii) .