(E)-2-{(2-Hydroxy-naphthalen-1-yl)methyl-ene}hydrazinecarboxamide.

In the title mol-ecule, C(12)H(11)N(3)O(2), the dihedral angle between the mean planes of the naphthalene and carboxamide groups is 28.9 (8)°. The hydrazine N atoms are twisted slightly out of the plane of the carboxamide group [C-C-N-N torsion angle = -175.06 (13)°]. The crystal packing is influenced by N-H⋯O hydrogen bonding which includes a bifurcated hydrogen bond between the amide N atom and nearby carboxyl and hydroxyl O atoms. A second bifurcated hydrogen bond occurs between the hydroxyl O atom and nearby amide (inter-molecular) and hydrazine (intra-molecular) N atoms. As a result, mol-ecules are linked into a co-operative hydrogen-bonded network of infinite one-dimensional O-H⋯O-H⋯O-H chains along the (101) plane of the unit cell in a zigzag pattern, the dihedral angle between the mean planes of the naphthalene groups of adjacent mol-ecules in the chain being 86.9 (2)°. A MOPAC PM3 calculation provides support to these observations.

Related literature

For related semicarbazones, see: Noblia et al. (2005 ▶). For the bioactivity of semicarbazones, see: Beraldo & Gambino (2004 ▶). For their applications in polymers, see: Khuhawar et al. (2004 ▶) and in sensors, see: Oter et al. (2007 ▶).

Experimental

Crystal data

C12H11N3O2

M = 229.24

Monoclinic,

a = 16.0886 (4) Å

b = 4.72900 (10) Å

c = 15.6452 (4) Å

β = 114.647 (3)°

V = 1081.89 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.82 mm−1

T = 200 K

0.57 × 0.22 × 0.12 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.819, T max = 0.907

7383 measured reflections

2135 independent reflections

1724 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.124

S = 1.03

2135 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and WebMOPro (Schmidt & Polik, 2007 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014561/rk2136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014561/rk2136Isup2.hkl

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

C12H11N3O2	F(000) = 480
Mr = 229.24	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4156 reflections
a = 16.0886 (4) Å	θ = 5.2–73.5°
b = 4.7290 (1) Å	µ = 0.82 mm−1
c = 15.6452 (4) Å	T = 200 K
β = 114.647 (3)°	Needle, pale yellow
V = 1081.89 (5) Å3	0.57 × 0.22 × 0.12 mm
Z = 4

Oxford Diffraction Gemini R diffractometer	2135 independent reflections
Radiation source: Fine–focus sealed tube	1724 reflections with I > 2σ(I)
Graphite	Rint = 0.031
Detector resolution: 10.5081 pixels mm-1	θmax = 73.5°, θmin = 5.7°
φ and ω scans	h = −18→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −4→5
Tmin = 0.819, Tmax = 0.907	l = −19→19
7383 measured reflections

Refinement on F2	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: Geom
wR(F2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0706P)2 + 0.3033P] where P = (Fo2 + 2Fc2)/3
2135 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.31323 (8)	0.7964 (3)	0.22177 (8)	0.0437 (3)
H1O	0.3498	0.6774	0.2579	0.052*
O2	0.56353 (8)	−0.0031 (2)	0.42849 (8)	0.0369 (3)
N1	0.38963 (8)	0.4986 (3)	0.37070 (9)	0.0317 (3)
N2	0.44479 (9)	0.2745 (3)	0.41411 (9)	0.0332 (3)
H2A	0.4322	0.1678	0.4533	0.040*
N3	0.54082 (10)	0.4022 (3)	0.34432 (10)	0.0391 (4)
H3A	0.5881	0.3706	0.3312	0.047*
H3B	0.5076	0.5557	0.3231	0.047*
C1	0.26235 (9)	0.7936 (3)	0.34640 (10)	0.0280 (3)
C2	0.25746 (10)	0.8928 (4)	0.26045 (10)	0.0325 (4)
C3	0.19255 (11)	1.0963 (4)	0.20808 (11)	0.0391 (4)
H3C	0.1902	1.1586	0.1494	0.047*
C4	0.13328 (11)	1.2044 (4)	0.24071 (12)	0.0386 (4)
H4A	0.0896	1.3413	0.2044	0.046*
C5	0.13540 (10)	1.1162 (3)	0.32839 (11)	0.0325 (4)
C6	0.07427 (11)	1.2315 (4)	0.36314 (12)	0.0408 (4)
H6A	0.0312	1.3707	0.3274	0.049*
C7	0.07638 (12)	1.1455 (4)	0.44726 (13)	0.0438 (4)
H7A	0.0345	1.2225	0.4694	0.053*
C8	0.14048 (12)	0.9437 (4)	0.50068 (12)	0.0414 (4)
H8A	0.1419	0.8849	0.5593	0.050*
C9	0.20126 (10)	0.8293 (4)	0.46977 (11)	0.0348 (4)
H9A	0.2447	0.6942	0.5077	0.042*
C10	0.20044 (9)	0.9091 (3)	0.38214 (10)	0.0287 (3)
C11	0.32667 (10)	0.5704 (3)	0.39663 (10)	0.0291 (3)
H11A	0.3220	0.4782	0.4484	0.035*
C12	0.51931 (10)	0.2162 (3)	0.39678 (10)	0.0303 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0468 (7)	0.0513 (8)	0.0418 (6)	0.0135 (6)	0.0272 (5)	0.0132 (5)
O2	0.0394 (6)	0.0298 (6)	0.0446 (6)	0.0091 (5)	0.0208 (5)	0.0026 (5)
N1	0.0305 (6)	0.0290 (7)	0.0354 (6)	0.0038 (5)	0.0135 (5)	0.0024 (5)
N2	0.0337 (7)	0.0283 (7)	0.0408 (7)	0.0063 (5)	0.0187 (6)	0.0074 (5)
N3	0.0418 (7)	0.0330 (8)	0.0523 (8)	0.0081 (6)	0.0293 (6)	0.0057 (6)
C1	0.0251 (7)	0.0271 (8)	0.0302 (7)	−0.0010 (6)	0.0098 (6)	0.0006 (6)
C2	0.0321 (8)	0.0330 (9)	0.0334 (7)	0.0003 (6)	0.0145 (6)	0.0011 (6)
C3	0.0410 (9)	0.0404 (10)	0.0333 (8)	0.0023 (7)	0.0129 (7)	0.0090 (7)
C4	0.0319 (8)	0.0347 (9)	0.0408 (8)	0.0056 (7)	0.0068 (6)	0.0065 (7)
C5	0.0252 (7)	0.0282 (8)	0.0400 (8)	−0.0020 (6)	0.0095 (6)	−0.0039 (6)
C6	0.0293 (8)	0.0355 (9)	0.0531 (10)	0.0042 (7)	0.0127 (7)	−0.0048 (7)
C7	0.0355 (8)	0.0447 (10)	0.0569 (10)	−0.0011 (7)	0.0249 (8)	−0.0148 (8)
C8	0.0410 (9)	0.0459 (10)	0.0426 (9)	−0.0037 (8)	0.0226 (7)	−0.0081 (8)
C9	0.0332 (8)	0.0363 (9)	0.0352 (8)	0.0024 (6)	0.0146 (6)	−0.0016 (6)
C10	0.0247 (7)	0.0263 (8)	0.0333 (7)	−0.0036 (6)	0.0103 (6)	−0.0045 (6)
C11	0.0293 (7)	0.0279 (8)	0.0296 (7)	−0.0002 (6)	0.0119 (6)	0.0002 (6)
C12	0.0305 (7)	0.0289 (8)	0.0310 (7)	0.0008 (6)	0.0125 (6)	−0.0044 (6)

O1—C2	1.3534 (19)	C3—H3C	0.9500
O1—H1O	0.8400	C4—C5	1.421 (2)
O2—C12	1.2386 (18)	C4—H4A	0.9500
N1—C11	1.284 (2)	C5—C6	1.416 (2)
N1—N2	1.3674 (18)	C5—C10	1.424 (2)
N2—C12	1.3630 (19)	C6—C7	1.364 (3)
N2—H2A	0.8800	C6—H6A	0.9500
N3—C12	1.343 (2)	C7—C8	1.398 (3)
N3—H3A	0.8800	C7—H7A	0.9500
N3—H3B	0.8800	C8—C9	1.370 (2)
C1—C2	1.395 (2)	C8—H8A	0.9500
C1—C10	1.438 (2)	C9—C10	1.417 (2)
C1—C11	1.457 (2)	C9—H9A	0.9500
C2—C3	1.405 (2)	C11—H11A	0.9500
C3—C4	1.355 (2)
C2—O1—H1O	109.5	C4—C5—C10	119.23 (14)
C11—N1—N2	118.82 (13)	C7—C6—C5	120.90 (16)
C12—N2—N1	120.02 (13)	C7—C6—H6A	119.6
C12—N2—H2A	120.0	C5—C6—H6A	119.6
N1—N2—H2A	120.0	C6—C7—C8	119.71 (16)
C12—N3—H3A	120.0	C6—C7—H7A	120.1
C12—N3—H3B	120.0	C8—C7—H7A	120.1
H3A—N3—H3B	120.0	C9—C8—C7	121.05 (16)
C2—C1—C10	118.52 (13)	C9—C8—H8A	119.5
C2—C1—C11	120.34 (14)	C7—C8—H8A	119.5
C10—C1—C11	121.10 (13)	C8—C9—C10	121.09 (15)
O1—C2—C1	122.44 (14)	C8—C9—H9A	119.5
O1—C2—C3	116.10 (14)	C10—C9—H9A	119.5
C1—C2—C3	121.45 (14)	C9—C10—C5	117.57 (14)
C4—C3—C2	120.48 (15)	C9—C10—C1	123.14 (14)
C4—C3—H3C	119.8	C5—C10—C1	119.29 (14)
C2—C3—H3C	119.8	N1—C11—C1	119.82 (13)
C3—C4—C5	121.03 (15)	N1—C11—H11A	120.1
C3—C4—H4A	119.5	C1—C11—H11A	120.1
C5—C4—H4A	119.5	O2—C12—N3	122.81 (14)
C6—C5—C4	121.10 (15)	O2—C12—N2	119.71 (14)
C6—C5—C10	119.67 (15)	N3—C12—N2	117.48 (14)
C11—N1—N2—C12	−171.55 (13)	C8—C9—C10—C5	1.2 (2)
C10—C1—C2—O1	179.81 (14)	C8—C9—C10—C1	−179.55 (15)
C11—C1—C2—O1	−2.4 (2)	C6—C5—C10—C9	−0.6 (2)
C10—C1—C2—C3	−1.4 (2)	C4—C5—C10—C9	179.18 (14)
C11—C1—C2—C3	176.35 (15)	C6—C5—C10—C1	−179.86 (14)
O1—C2—C3—C4	179.62 (15)	C4—C5—C10—C1	−0.1 (2)
C1—C2—C3—C4	0.8 (3)	C2—C1—C10—C9	−178.19 (14)
C2—C3—C4—C5	0.2 (3)	C11—C1—C10—C9	4.1 (2)
C3—C4—C5—C6	179.19 (15)	C2—C1—C10—C5	1.1 (2)
C3—C4—C5—C10	−0.5 (2)	C11—C1—C10—C5	−176.66 (13)
C4—C5—C6—C7	179.81 (15)	N2—N1—C11—C1	−175.06 (13)
C10—C5—C6—C7	−0.5 (2)	C2—C1—C11—N1	12.1 (2)
C5—C6—C7—C8	0.9 (3)	C10—C1—C11—N1	−170.23 (13)
C6—C7—C8—C9	−0.3 (3)	N1—N2—C12—O2	−172.55 (13)
C7—C8—C9—C10	−0.8 (3)	N1—N2—C12—N3	6.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.84	1.82	2.5562 (17)	146
N2—H2A···O2i	0.88	1.98	2.8290 (17)	161
N3—H3A···O1ii	0.88	2.10	2.9762 (18)	171
N3—H3B···O2iii	0.88	2.58	3.0618 (18)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.84	1.82	2.5562 (17)	146
N2—H2A⋯O2i	0.88	1.98	2.8290 (17)	161
N3—H3A⋯O1ii	0.88	2.10	2.9762 (18)	171
N3—H3B⋯O2iii	0.88	2.58	3.0618 (18)	116

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