(E)-2-Hydroxy-naphthalene-1-carb-al-de-hyde semicarbazone.

The title compound, C(12)H(11)N(3)O(2), adopts an E or trans configuration with respect to the C=N bond. There is an intra-molecular O-H⋯N hydrogen bond involving the hydroxyl H atom and an N atom of the hydrazine group. In the crystal structure, mol-ecules are connected via N-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the potential pharmacological and anti­tumor properties of hydrazones and Schiff bases, see: Karthikeyan et al. (2006 ▶); Khattab (2005 ▶); Kucukguzel et al. (2006 ▶). For related structures, see: Okabe et al. (1993 ▶); Zhang et al. (1999 ▶); Xu et al. (2009 ▶).

Experimental

Crystal data

C12H11N3O2

M = 229.24

Monoclinic,

a = 16.091 (3) Å

b = 4.7350 (9) Å

c = 15.776 (3) Å

β = 114.26 (3)°

V = 1095.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 283 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.988, T max = 0.989

6629 measured reflections

2324 independent reflections

1550 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.05

2324 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901174X/su2105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901174X/su2105Isup2.hkl

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

C12H11N3O2	F(000) = 480
Mr = 229.24	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 628 reflections
a = 16.091 (3) Å	θ = 2.5–15°
b = 4.7350 (9) Å	µ = 0.10 mm−1
c = 15.776 (3) Å	T = 283 K
β = 114.26 (3)°	Block, yellow
V = 1095.8 (4) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2324 independent reflections
Radiation source: fine-focus sealed tube	1550 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.988, Tmax = 0.989	k = −6→4
6629 measured reflections	l = −19→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3
2324 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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
C1	0.23742 (8)	0.2085 (3)	0.15396 (8)	0.0367 (3)
C2	0.24256 (9)	0.1120 (3)	0.23930 (9)	0.0441 (3)
C3	0.30716 (10)	−0.0898 (3)	0.29109 (10)	0.0538 (4)
H3C	0.3094	−0.1497	0.3481	0.065*
C4	0.36618 (10)	−0.1978 (3)	0.25859 (10)	0.0530 (4)
H4A	0.4089	−0.3307	0.2939	0.064*
C5	0.36419 (8)	−0.1126 (3)	0.17185 (9)	0.0435 (3)
C6	0.42499 (10)	−0.2280 (3)	0.13721 (11)	0.0572 (4)
H6A	0.4674	−0.3622	0.1722	0.069*
C7	0.42258 (10)	−0.1462 (4)	0.05361 (12)	0.0623 (4)
H7A	0.4634	−0.2231	0.0320	0.075*
C8	0.35881 (11)	0.0531 (3)	0.00052 (11)	0.0571 (4)
H8A	0.3572	0.1088	−0.0567	0.068*
C9	0.29852 (9)	0.1678 (3)	0.03161 (9)	0.0477 (4)
H9A	0.2560	0.2989	−0.0053	0.057*
C10	0.29938 (8)	0.0915 (3)	0.11853 (9)	0.0377 (3)
C11	0.17325 (8)	0.4299 (3)	0.10430 (9)	0.0383 (3)
H11	0.1777	0.5185	0.0537	0.046*
C12	−0.01922 (9)	0.7854 (3)	0.10281 (9)	0.0405 (3)
N1	0.11062 (7)	0.5029 (2)	0.13008 (7)	0.0419 (3)
N2	0.05492 (7)	0.7251 (2)	0.08591 (7)	0.0447 (3)
H2	0.0671	0.8266	0.0473	0.054*
N3	−0.04085 (8)	0.6020 (3)	0.15536 (8)	0.0551 (4)
H3A	−0.0873	0.6333	0.1678	0.066*
H3B	−0.0083	0.4530	0.1765	0.066*
O1	0.18694 (7)	0.2086 (2)	0.27791 (7)	0.0616 (3)
H1	0.1521	0.3272	0.2436	0.092*
O2	−0.06341 (7)	1.00232 (19)	0.07058 (6)	0.0510 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0325 (6)	0.0356 (7)	0.0400 (7)	−0.0004 (5)	0.0127 (6)	0.0012 (6)
C2	0.0426 (7)	0.0456 (8)	0.0445 (7)	0.0005 (6)	0.0183 (6)	0.0036 (6)
C3	0.0547 (9)	0.0555 (9)	0.0458 (8)	0.0047 (7)	0.0151 (7)	0.0146 (7)
C4	0.0425 (8)	0.0467 (9)	0.0575 (9)	0.0073 (7)	0.0080 (7)	0.0094 (7)
C5	0.0317 (7)	0.0378 (8)	0.0543 (8)	−0.0019 (6)	0.0108 (6)	−0.0042 (6)
C6	0.0386 (8)	0.0501 (9)	0.0765 (11)	0.0066 (7)	0.0172 (7)	−0.0063 (8)
C7	0.0479 (8)	0.0625 (11)	0.0841 (12)	0.0004 (8)	0.0347 (8)	−0.0223 (9)
C8	0.0560 (9)	0.0636 (10)	0.0593 (9)	−0.0035 (8)	0.0313 (8)	−0.0097 (8)
C9	0.0436 (8)	0.0519 (9)	0.0478 (8)	0.0035 (6)	0.0191 (7)	−0.0028 (6)
C10	0.0313 (6)	0.0356 (7)	0.0438 (7)	−0.0040 (5)	0.0131 (6)	−0.0052 (6)
C11	0.0371 (7)	0.0381 (8)	0.0389 (7)	−0.0001 (6)	0.0150 (6)	0.0004 (6)
C12	0.0416 (7)	0.0368 (8)	0.0434 (7)	0.0014 (6)	0.0177 (6)	−0.0071 (6)
N1	0.0385 (6)	0.0396 (6)	0.0480 (6)	0.0057 (5)	0.0182 (5)	0.0030 (5)
N2	0.0428 (6)	0.0401 (7)	0.0560 (7)	0.0097 (5)	0.0250 (6)	0.0108 (5)
N3	0.0579 (8)	0.0484 (8)	0.0733 (8)	0.0123 (6)	0.0414 (7)	0.0112 (6)
O1	0.0642 (7)	0.0759 (8)	0.0575 (6)	0.0184 (6)	0.0378 (6)	0.0190 (5)
O2	0.0525 (6)	0.0432 (6)	0.0616 (6)	0.0139 (5)	0.0280 (5)	0.0039 (5)

C1—C2	1.3916 (17)	C8—C9	1.3667 (18)
C1—C10	1.4390 (16)	C8—H8A	0.9300
C1—C11	1.4540 (17)	C9—C10	1.4126 (18)
C2—O1	1.3525 (15)	C9—H9A	0.9300
C2—C3	1.4013 (19)	C11—N1	1.2798 (15)
C3—C4	1.352 (2)	C11—H11	0.9300
C3—H3C	0.9300	C12—O2	1.2336 (14)
C4—C5	1.414 (2)	C12—N3	1.3417 (16)
C4—H4A	0.9300	C12—N2	1.3554 (15)
C5—C6	1.4120 (19)	N1—N2	1.3719 (14)
C5—C10	1.4172 (18)	N2—H2	0.8600
C6—C7	1.360 (2)	N3—H3A	0.8600
C6—H6A	0.9300	N3—H3B	0.8600
C7—C8	1.392 (2)	O1—H1	0.8200
C7—H7A	0.9300
C2—C1—C10	118.31 (12)	C9—C8—H8A	119.7
C2—C1—C11	120.31 (11)	C7—C8—H8A	119.7
C10—C1—C11	121.34 (11)	C8—C9—C10	121.44 (14)
O1—C2—C1	122.52 (12)	C8—C9—H9A	119.3
O1—C2—C3	115.95 (12)	C10—C9—H9A	119.3
C1—C2—C3	121.53 (12)	C9—C10—C5	117.51 (11)
C4—C3—C2	120.36 (13)	C9—C10—C1	123.13 (12)
C4—C3—H3C	119.8	C5—C10—C1	119.36 (11)
C2—C3—H3C	119.8	N1—C11—C1	120.08 (11)
C3—C4—C5	121.27 (13)	N1—C11—H11	120.0
C3—C4—H4A	119.4	C1—C11—H11	120.0
C5—C4—H4A	119.4	O2—C12—N3	122.80 (12)
C6—C5—C4	121.35 (14)	O2—C12—N2	119.96 (12)
C6—C5—C10	119.48 (13)	N3—C12—N2	117.24 (12)
C4—C5—C10	119.17 (12)	C11—N1—N2	118.76 (10)
C7—C6—C5	121.13 (15)	C12—N2—N1	120.39 (10)
C7—C6—H6A	119.4	C12—N2—H2	119.8
C5—C6—H6A	119.4	N1—N2—H2	119.8
C6—C7—C8	119.79 (13)	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	120.64 (14)	C2—O1—H1	109.5
C10—C1—C2—O1	−179.71 (12)	C8—C9—C10—C1	179.65 (12)
C11—C1—C2—O1	2.7 (2)	C6—C5—C10—C9	0.63 (18)
C10—C1—C2—C3	1.2 (2)	C4—C5—C10—C9	−179.00 (12)
C11—C1—C2—C3	−176.41 (13)	C6—C5—C10—C1	179.93 (12)
O1—C2—C3—C4	−179.60 (13)	C4—C5—C10—C1	0.30 (18)
C1—C2—C3—C4	−0.4 (2)	C2—C1—C10—C9	178.15 (12)
C2—C3—C4—C5	−0.4 (2)	C11—C1—C10—C9	−4.27 (19)
C3—C4—C5—C6	−179.15 (13)	C2—C1—C10—C5	−1.10 (18)
C3—C4—C5—C10	0.5 (2)	C11—C1—C10—C5	176.48 (11)
C4—C5—C6—C7	179.75 (13)	C2—C1—C11—N1	−12.17 (19)
C10—C5—C6—C7	0.1 (2)	C10—C1—C11—N1	170.30 (11)
C5—C6—C7—C8	−0.5 (2)	C1—C11—N1—N2	175.68 (11)
C6—C7—C8—C9	0.0 (2)	O2—C12—N2—N1	172.35 (11)
C7—C8—C9—C10	0.8 (2)	N3—C12—N2—N1	−7.35 (18)
C8—C9—C10—C5	−1.1 (2)	C11—N1—N2—C12	171.46 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.5563 (15)	146
N2—H2···O2i	0.86	2.01	2.8385 (15)	163
N3—H3A···O1ii	0.86	2.14	2.9871 (15)	171
N3—H3B···O2iii	0.86	2.63	3.0957 (16)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.5563 (15)	146
N2—H2⋯O2i	0.86	2.01	2.8385 (15)	163
N3—H3A⋯O1ii	0.86	2.14	2.9871 (15)	171
N3—H3B⋯O2iii	0.86	2.63	3.0957 (16)	115

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