N'-[(E)-Furan-2-yl-methyl-idene]pyridine-3-carbohydrazide.

The title compound, C(11)H(9)N(3)O(2), exists in the E conformation with respect to the azomethane C=N bond, and has the keto form. There are two independent mol-ecules in the asymmetric unit and each of these features a slight slanting of the pyridine and furan rings, which form a dihedral angle of 14.96 (10)° in one of the mol-ecules and 5.53 (10)° in the other. The crystal structure is stabilized by N-H⋯O and N-H⋯N hydrogen bonds, weak C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π inter-actions and π-π inter-actions [shortest centroid-centroid distance = 3.7864 (15) Å].

Related literature

For applications of carbohydrazide in non-linear optics and mol­ecular sensing, see: Bakir & Brown (2002 ▶). For the synthesis of related compounds, see: Fun et al. (2008 ▶); Neema & Kurup (2011 ▶). For similar structures, see: Nancy et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H9N3O2

M = 215.21

Triclinic,

a = 9.441 (2) Å

b = 10.237 (3) Å

c = 11.023 (2) Å

α = 75.10 (2)°

β = 85.413 (19)°

γ = 84.11 (2)°

V = 1022.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.26 × 0.21 × 0.18 mm

Data collection

Bruker P4 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.975, T max = 0.982

9430 measured reflections

3589 independent reflections

2702 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.117

S = 1.09

3589 reflections

298 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046381/tk5012sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046381/tk5012Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046381/tk5012Isup3.cml

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

C11H9N3O2	Z = 4
Mr = 215.21	F(000) = 448
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.441 (2) Å	Cell parameters from 2702 reflections
b = 10.237 (3) Å	θ = 3.0–25.0°
c = 11.023 (2) Å	µ = 0.10 mm−1
α = 75.10 (2)°	T = 150 K
β = 85.413 (19)°	Block, light-green
γ = 84.11 (2)°	0.26 × 0.21 × 0.18 mm
V = 1022.5 (4) Å3

Bruker P4 diffractometer	3589 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2702 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 8.33 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −12→11
Tmin = 0.975, Tmax = 0.982	l = −12→13
9430 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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.0667P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3589 reflections	Δρmax = 0.22 e Å−3
298 parameters	Δρmin = −0.29 e Å−3
2 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: 0.008 (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
O1	0.61774 (13)	−0.01358 (13)	0.71738 (12)	0.0408 (4)
O2	1.11415 (15)	0.10175 (14)	0.58530 (13)	0.0488 (4)
O3	0.76963 (14)	0.26997 (12)	0.97572 (11)	0.0373 (3)
O4	0.43780 (16)	0.54591 (14)	0.67271 (14)	0.0557 (4)
N1	0.32366 (15)	0.25812 (14)	0.94601 (14)	0.0331 (4)
N2	0.71582 (15)	0.15648 (15)	0.76984 (13)	0.0293 (4)
N3	0.84450 (15)	0.13134 (15)	0.70761 (13)	0.0306 (4)
N4	1.00763 (16)	0.47023 (16)	1.23845 (14)	0.0368 (4)
N5	0.70930 (14)	0.49236 (15)	0.96475 (13)	0.0268 (3)
N6	0.62315 (15)	0.50278 (15)	0.86641 (13)	0.0283 (3)
C1	0.2301 (2)	0.16377 (19)	0.97664 (17)	0.0355 (4)
H1	0.1473	0.1808	1.0237	0.043*
C2	0.24961 (19)	0.04281 (18)	0.94233 (17)	0.0329 (4)
H2	0.1806	−0.0191	0.9640	0.039*
C3	0.37305 (18)	0.01569 (17)	0.87553 (16)	0.0307 (4)
H3	0.3890	−0.0656	0.8516	0.037*
C4	0.47390 (18)	0.10983 (17)	0.84378 (15)	0.0267 (4)
C5	0.44343 (18)	0.23048 (17)	0.88037 (16)	0.0300 (4)
H5	0.5096	0.2951	0.8581	0.036*
C6	0.60870 (18)	0.07795 (17)	0.77142 (16)	0.0288 (4)
C7	0.94024 (19)	0.21070 (18)	0.71100 (16)	0.0316 (4)
H7	0.9194	0.2776	0.7546	0.038*
C8	1.07818 (19)	0.19826 (19)	0.64918 (16)	0.0337 (4)
C9	1.18880 (17)	0.27331 (18)	0.64346 (15)	0.0294 (4)
H9	1.1906	0.3450	0.6806	0.035*
C10	1.3003 (2)	0.2241 (2)	0.57180 (17)	0.0404 (5)
H10	1.3897	0.2571	0.5519	0.049*
C11	1.2542 (2)	0.1210 (2)	0.53733 (18)	0.0458 (5)
H11	1.3072	0.0695	0.4886	0.055*
C12	1.0577 (2)	0.3466 (2)	1.30061 (17)	0.0386 (5)
H12	1.1209	0.3400	1.3629	0.046*
C13	1.0218 (2)	0.2281 (2)	1.27846 (18)	0.0397 (5)
H13	1.0602	0.1442	1.3241	0.048*
C14	0.92747 (19)	0.23689 (18)	1.18683 (16)	0.0340 (4)
H14	0.9003	0.1585	1.1706	0.041*
C15	0.87333 (17)	0.36337 (17)	1.11913 (15)	0.0262 (4)
C16	0.91764 (18)	0.47580 (18)	1.14965 (16)	0.0318 (4)
H16	0.8819	0.5611	1.1048	0.038*
C17	0.77872 (18)	0.37120 (17)	1.01468 (15)	0.0267 (4)
C18	0.57217 (18)	0.62304 (18)	0.81434 (16)	0.0293 (4)
H18	0.5977	0.6954	0.8421	0.035*
C19	0.47684 (18)	0.64921 (18)	0.71446 (16)	0.0316 (4)
C20	0.41102 (18)	0.76644 (18)	0.65139 (15)	0.0302 (4)
H20	0.4195	0.8518	0.6636	0.036*
C21	0.32700 (19)	0.7377 (2)	0.56365 (17)	0.0369 (5)
H21	0.2697	0.7994	0.5068	0.044*
C22	0.3457 (2)	0.6057 (2)	0.5781 (2)	0.0546 (6)
H22	0.3028	0.5586	0.5312	0.066*
H2N	0.7125 (19)	0.2127 (17)	0.8202 (16)	0.035 (5)*
H5N	0.713 (2)	0.5638 (17)	0.9912 (18)	0.043 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0418 (8)	0.0409 (8)	0.0502 (8)	−0.0061 (6)	0.0002 (6)	−0.0300 (7)
O2	0.0606 (9)	0.0428 (9)	0.0435 (8)	−0.0036 (7)	−0.0011 (7)	−0.0126 (7)
O3	0.0526 (8)	0.0267 (7)	0.0372 (7)	−0.0020 (6)	−0.0121 (6)	−0.0139 (6)
O4	0.0671 (10)	0.0386 (9)	0.0648 (10)	−0.0073 (7)	−0.0282 (8)	−0.0108 (7)
N1	0.0369 (9)	0.0286 (9)	0.0363 (9)	0.0003 (7)	−0.0034 (7)	−0.0137 (7)
N2	0.0332 (8)	0.0302 (9)	0.0293 (8)	−0.0044 (7)	−0.0002 (6)	−0.0158 (7)
N3	0.0342 (8)	0.0318 (9)	0.0273 (8)	−0.0021 (7)	−0.0019 (6)	−0.0105 (6)
N4	0.0373 (9)	0.0377 (10)	0.0394 (9)	−0.0021 (7)	−0.0085 (7)	−0.0152 (8)
N5	0.0296 (8)	0.0256 (9)	0.0286 (8)	−0.0016 (6)	−0.0047 (6)	−0.0126 (7)
N6	0.0290 (8)	0.0300 (9)	0.0282 (8)	−0.0037 (6)	−0.0042 (6)	−0.0105 (6)
C1	0.0370 (10)	0.0353 (11)	0.0354 (10)	−0.0026 (9)	0.0004 (8)	−0.0118 (9)
C2	0.0356 (10)	0.0267 (10)	0.0360 (10)	−0.0059 (8)	−0.0032 (8)	−0.0057 (8)
C3	0.0394 (10)	0.0224 (10)	0.0327 (10)	−0.0017 (8)	−0.0051 (8)	−0.0107 (8)
C4	0.0340 (10)	0.0250 (9)	0.0230 (9)	−0.0010 (7)	−0.0075 (7)	−0.0081 (7)
C5	0.0325 (10)	0.0282 (10)	0.0317 (10)	−0.0041 (8)	−0.0060 (8)	−0.0102 (8)
C6	0.0351 (10)	0.0265 (10)	0.0272 (9)	−0.0011 (8)	−0.0061 (7)	−0.0102 (8)
C7	0.0375 (10)	0.0317 (10)	0.0282 (10)	−0.0046 (8)	−0.0023 (8)	−0.0110 (8)
C8	0.0403 (11)	0.0367 (11)	0.0250 (9)	−0.0016 (8)	−0.0045 (8)	−0.0090 (8)
C9	0.0281 (9)	0.0377 (11)	0.0271 (9)	−0.0072 (8)	−0.0001 (7)	−0.0151 (8)
C10	0.0329 (10)	0.0528 (13)	0.0329 (10)	−0.0011 (9)	−0.0028 (8)	−0.0065 (9)
C11	0.0503 (13)	0.0470 (13)	0.0343 (11)	0.0125 (10)	0.0017 (9)	−0.0076 (10)
C12	0.0370 (11)	0.0459 (13)	0.0347 (11)	0.0010 (9)	−0.0094 (8)	−0.0132 (9)
C13	0.0501 (12)	0.0345 (11)	0.0344 (10)	0.0041 (9)	−0.0126 (9)	−0.0084 (8)
C14	0.0433 (11)	0.0295 (11)	0.0319 (10)	−0.0020 (8)	−0.0030 (8)	−0.0127 (8)
C15	0.0268 (9)	0.0270 (10)	0.0262 (9)	−0.0006 (7)	0.0017 (7)	−0.0105 (7)
C16	0.0348 (10)	0.0290 (10)	0.0329 (10)	−0.0011 (8)	−0.0060 (8)	−0.0098 (8)
C17	0.0309 (9)	0.0252 (10)	0.0256 (9)	−0.0040 (7)	0.0025 (7)	−0.0101 (7)
C18	0.0313 (9)	0.0289 (11)	0.0292 (10)	−0.0036 (8)	0.0001 (7)	−0.0103 (8)
C19	0.0312 (10)	0.0342 (11)	0.0302 (10)	−0.0073 (8)	0.0014 (7)	−0.0086 (8)
C20	0.0329 (10)	0.0320 (10)	0.0276 (9)	0.0022 (8)	−0.0036 (7)	−0.0125 (8)
C21	0.0351 (11)	0.0438 (13)	0.0311 (10)	−0.0036 (9)	−0.0056 (8)	−0.0067 (9)
C22	0.0612 (15)	0.0515 (15)	0.0581 (14)	−0.0118 (11)	−0.0262 (11)	−0.0167 (11)

O1—C6	1.2258 (19)	C5—H5	0.9300
O2—C8	1.356 (2)	C7—C8	1.430 (2)
O2—C11	1.398 (2)	C7—H7	0.9300
O3—C17	1.2325 (19)	C8—C9	1.347 (2)
O4—C19	1.350 (2)	C9—C10	1.396 (2)
O4—C22	1.388 (3)	C9—H9	0.9300
N1—C1	1.337 (2)	C10—C11	1.333 (3)
N1—C5	1.338 (2)	C10—H10	0.9300
N2—C6	1.351 (2)	C11—H11	0.9300
N2—N3	1.381 (2)	C12—C13	1.377 (3)
N2—H2N	0.893 (14)	C12—H12	0.9300
N3—C7	1.285 (2)	C13—C14	1.379 (3)
N4—C12	1.333 (2)	C13—H13	0.9300
N4—C16	1.333 (2)	C14—C15	1.387 (2)
N5—C17	1.346 (2)	C14—H14	0.9300
N5—N6	1.383 (2)	C15—C16	1.390 (2)
N5—H5N	0.858 (15)	C15—C17	1.494 (2)
N6—C18	1.279 (2)	C16—H16	0.9300
C1—C2	1.376 (2)	C18—C19	1.432 (3)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.371 (2)	C19—C20	1.340 (2)
C2—H2	0.9300	C20—C21	1.403 (2)
C3—C4	1.385 (2)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.314 (3)
C4—C5	1.391 (2)	C21—H21	0.9300
C4—C6	1.499 (2)	C22—H22	0.9300
C8—O2—C11	105.59 (15)	C11—C10—C9	106.90 (17)
C19—O4—C22	105.42 (15)	C11—C10—H10	126.6
C1—N1—C5	117.26 (15)	C9—C10—H10	126.6
C6—N2—N3	119.18 (14)	C10—C11—O2	109.84 (16)
C6—N2—H2N	121.8 (12)	C10—C11—H11	125.1
N3—N2—H2N	117.9 (12)	O2—C11—H11	125.1
C7—N3—N2	114.99 (14)	N4—C12—C13	124.17 (18)
C12—N4—C16	116.25 (16)	N4—C12—H12	117.9
C17—N5—N6	118.33 (14)	C13—C12—H12	117.9
C17—N5—H5N	124.5 (14)	C12—C13—C14	118.32 (18)
N6—N5—H5N	117.2 (14)	C12—C13—H13	120.8
C18—N6—N5	115.34 (14)	C14—C13—H13	120.8
N1—C1—C2	123.62 (17)	C13—C14—C15	119.56 (17)
N1—C1—H1	118.2	C13—C14—H14	120.2
C2—C1—H1	118.2	C15—C14—H14	120.2
C3—C2—C1	118.45 (17)	C14—C15—C16	116.92 (16)
C3—C2—H2	120.8	C14—C15—C17	118.80 (15)
C1—C2—H2	120.8	C16—C15—C17	124.18 (16)
C2—C3—C4	119.73 (15)	N4—C16—C15	124.78 (17)
C2—C3—H3	120.1	N4—C16—H16	117.6
C4—C3—H3	120.1	C15—C16—H16	117.6
C3—C4—C5	117.67 (15)	O3—C17—N5	122.79 (16)
C3—C4—C6	118.95 (14)	O3—C17—C15	119.94 (15)
C5—C4—C6	123.37 (15)	N5—C17—C15	117.25 (14)
N1—C5—C4	123.25 (16)	N6—C18—C19	121.73 (16)
N1—C5—H5	118.4	N6—C18—H18	119.1
C4—C5—H5	118.4	C19—C18—H18	119.1
O1—C6—N2	123.49 (16)	C20—C19—O4	109.62 (16)
O1—C6—C4	120.77 (15)	C20—C19—C18	130.05 (17)
N2—C6—C4	115.74 (14)	O4—C19—C18	120.31 (16)
N3—C7—C8	121.36 (16)	C19—C20—C21	107.93 (17)
N3—C7—H7	119.3	C19—C20—H20	126.0
C8—C7—H7	119.3	C21—C20—H20	126.0
C9—C8—O2	109.95 (15)	C22—C21—C20	106.02 (18)
C9—C8—C7	128.47 (17)	C22—C21—H21	127.0
O2—C8—C7	121.59 (16)	C20—C21—H21	127.0
C8—C9—C10	107.72 (16)	C21—C22—O4	111.01 (18)
C8—C9—H9	126.1	C21—C22—H22	124.5
C10—C9—H9	126.1	O4—C22—H22	124.5
C6—N2—N3—C7	−179.93 (16)	C8—O2—C11—C10	0.4 (2)
C17—N5—N6—C18	−172.91 (14)	C16—N4—C12—C13	−0.2 (3)
C5—N1—C1—C2	−1.3 (3)	N4—C12—C13—C14	−0.4 (3)
N1—C1—C2—C3	1.6 (3)	C12—C13—C14—C15	0.8 (3)
C1—C2—C3—C4	−0.4 (3)	C13—C14—C15—C16	−0.7 (2)
C2—C3—C4—C5	−0.9 (2)	C13—C14—C15—C17	176.09 (15)
C2—C3—C4—C6	179.60 (16)	C12—N4—C16—C15	0.4 (3)
C1—N1—C5—C4	−0.1 (3)	C14—C15—C16—N4	0.1 (3)
C3—C4—C5—N1	1.2 (3)	C17—C15—C16—N4	−176.49 (15)
C6—C4—C5—N1	−179.32 (16)	N6—N5—C17—O3	0.7 (2)
N3—N2—C6—O1	−2.0 (3)	N6—N5—C17—C15	178.83 (13)
N3—N2—C6—C4	178.51 (14)	C14—C15—C17—O3	−12.5 (2)
C3—C4—C6—O1	15.9 (2)	C16—C15—C17—O3	163.98 (16)
C5—C4—C6—O1	−163.54 (17)	C14—C15—C17—N5	169.29 (15)
C3—C4—C6—N2	−164.56 (15)	C16—C15—C17—N5	−14.2 (2)
C5—C4—C6—N2	16.0 (2)	N5—N6—C18—C19	−177.59 (14)
N2—N3—C7—C8	−179.07 (15)	C22—O4—C19—C20	1.1 (2)
C11—O2—C8—C9	−0.6 (2)	C22—O4—C19—C18	179.52 (16)
C11—O2—C8—C7	179.48 (16)	N6—C18—C19—C20	178.28 (17)
N3—C7—C8—C9	179.63 (18)	N6—C18—C19—O4	0.2 (2)
N3—C7—C8—O2	−0.5 (3)	O4—C19—C20—C21	−0.8 (2)
O2—C8—C9—C10	0.6 (2)	C18—C19—C20—C21	−179.05 (17)
C7—C8—C9—C10	−179.48 (18)	C19—C20—C21—C22	0.2 (2)
C8—C9—C10—C11	−0.4 (2)	C20—C21—C22—O4	0.5 (2)
C9—C10—C11—O2	0.0 (2)	C19—O4—C22—C21	−1.0 (2)

Cg1 and Cg2 are the centroids of the O4/C19–C22 and O2/C8–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N1i	0.86 (2)	2.10 (2)	2.944 (2)	169.(2)
N2—H2N···O3	0.89 (1)	2.08 (2)	2.9017 (19)	154.(2)
C21—H21···N3ii	0.93	2.58	3.410 (3)	149.
C16—H16···N1i	0.93	2.53	3.370 (3)	150.
C11—H11···O1iii	0.93	2.51	3.365 (2)	153.
C2—H2···O3iv	0.93	2.49	3.116 (2)	125.
C10—H10···Cg1v	0.93	2.78	3.594 (2)	146
C12—H12···Cg2vi	0.93	2.75	3.520 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the O4/C19–C22 and O2/C8–C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯N1i	0.86 (2)	2.10 (2)	2.944 (2)	169 (2)
N2—H2N⋯O3	0.89 (1)	2.08 (2)	2.9017 (19)	154 (2)
C21—H21⋯N3ii	0.93	2.58	3.410 (3)	149
C16—H16⋯N1i	0.93	2.53	3.370 (3)	150
C11—H11⋯O1iii	0.93	2.51	3.365 (2)	153
C2—H2⋯O3iv	0.93	2.49	3.116 (2)	125
C10—H10⋯Cg1v	0.93	2.78	3.594 (2)	146
C12—H12⋯Cg2vi	0.93	2.75	3.520 (2)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .