(E)-2-Hydroxy­naphthalene-1-carb­al­de­hyde semicarbazone

The title compound, C₁₂H₁₁N₃O₂, adopts an E or trans configuration with respect to the C=N bond. There is an intra­molecular O—H...N hydrogen bond involving the hydroxyl H atom and an N atom of the hydrazine group. In the crystal structure, mol­ecules are connected via N—H...O hydrogen bonds, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 283 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.107
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   283.000
            Value of melting point given =     0.000
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B    ..  O2      ..       2.63 Ang.

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). As we are interested in this field of research (Xu et al. 2009), we report herein on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1 and geometrical parameters are given in the archived CIF. The molecule has a trans configuration about the C=N bond. There is an intramolecular O-H···N hydrogen bond involving the naphthalene hydroxyl sunstituent and atom N1 of the hydrazine group (Table 1).

In the crystal structure symmetry related molecules are connected via N-H···O hydrogen bonds so forming a three-dimensional structure (Table 1 and Fig. 2).

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).

S2. Experimental

The ligand H₂L was prepared according to the reported procedure (Zhang et al., 1999). A solution of semicarbazide hydrochloride (0.112 g, 1 mmol) in 5 ml of ethanol was added slowly to a solution of 2-hydro-1- naphthaldehyde (0.172 g,1 mmol) in 15 ml absolute ethanol, under heating and stirring. The mixture was refluxed for 3 h, then cooled to rt and left to stand in air for 5 days. Yellow block-shaped crystals were formed on slow evaporation of the solvent.

S3. Refinement

All the H-atoms were placed in calculated positions [O—H = 0.82 Å, N—H = 0.86 Å, C—H = 0.93 Å] and treated as riding [U_iso(H) = 1.5U_eq(parent O-atom) and = 1.2U_eq(parent C-atom and N-atom)].

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids (H-atoms have been omitted for clarity).
	Fig. 2. Crystal packing of the title compound viewed along the b axis. The intra- and intermolecular hydrogen bonds are shown as dashed lines (details are given in Table 1).

(E)-2-Hydroxynaphthalene-1-carbaldehyde semicarbazone

Crystal data

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) Å^3	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2324 independent reflections
Radiation source: fine-focus sealed tube	1550 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0607P)^2] where P = (Fo^2 + 2Fc^2)/3
2324 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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···O2^i	0.86	2.01	2.8385 (15)	163
N3—H3A···O1^ii	0.86	2.14	2.9871 (15)	171
N3—H3B···O2^iii	0.86	2.63	3.0957 (16)	115

Symmetry codes: (i) −x, −y+2, −z; (ii) −x, y+1/2, −z+1/2; (iii) x, y−1, z.