(E)-1-[(2-Hy-droxy-1-naphth-yl)methyl-idene-amino]-imidazolidine-2,4-dione.

The title compound, C(14)H(11)N(3)O(3), adopts an E or trans configuration with respect to the C=N bond. In the mol-ecule there is an intra-molecular O-H⋯N hydrogen bond involving the hy-droxy substituent at the 2-positon of the naphthalene ring and the adjacent methyl-ene-amino N atom. The mol-ecule is roughly planar, the dihedral angle between the naphthalene and imidazolidine-2,4-dione mean planes being 8.4 (1)°. In the crystal, pairs of N-H⋯O hydrogen bonds link mol-ecules into inversion dimers. These dimers are futher linked via C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For the naphthalene group as a fluoro­phore, see: Li et al. (2010 ▶); Iijima et al. (2010 ▶). For a related structure, see: Xu et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11N3O3

M = 269.26

Monoclinic,

a = 11.5122 (7) Å

b = 6.0233 (3) Å

c = 17.9955 (10) Å

β = 96.773 (5)°

V = 1239.13 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.40 × 0.30 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.959, T max = 0.969

4288 measured reflections

2136 independent reflections

1053 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.067

S = 0.72

2136 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020118/su2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020118/su2180Isup2.hkl

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

C14H11N3O3	F(000) = 560
Mr = 269.26	Dx = 1.443 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1596 reflections
a = 11.5122 (7) Å	θ = 3.1–29.0°
b = 6.0233 (3) Å	µ = 0.11 mm−1
c = 17.9955 (10) Å	T = 293 K
β = 96.773 (5)°	Block, yellow
V = 1239.13 (12) Å3	0.40 × 0.30 × 0.30 mm
Z = 4

Oxford Diffraction Gemini S Ultra diffractometer	2136 independent reflections
Radiation source: fine-focus sealed tube	1053 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 15.9149 pixels mm-1	θmax = 25.0°, θmin = 3.6°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = 0→6
Tmin = 0.959, Tmax = 0.969	l = 0→21
4288 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 0.72	w = 1/[σ2(Fo2) + (0.0266P)2] where P = (Fo2 + 2Fc2)/3
2136 reflections	(Δ/σ)max = 0.002
186 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm CrysAlisPro (Oxford Diffraction, 2009).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.59888 (11)	0.25607 (18)	0.48396 (8)	0.0491 (5)
O2	0.40014 (13)	0.1526 (2)	0.68676 (8)	0.0710 (7)
O3	0.80499 (13)	0.8397 (2)	0.49453 (8)	0.0645 (6)
N1	0.67397 (13)	0.6177 (2)	0.57838 (9)	0.0420 (6)
N2	0.59925 (13)	0.4517 (2)	0.59460 (9)	0.0425 (6)
N3	0.48790 (15)	0.1552 (3)	0.57835 (10)	0.0454 (7)
C1	0.79653 (19)	1.2321 (3)	0.80751 (14)	0.0665 (10)
C2	0.8627 (2)	1.4184 (4)	0.79511 (16)	0.0705 (10)
C3	0.90328 (19)	1.4454 (3)	0.72772 (16)	0.0626 (9)
C4	0.87808 (17)	1.2884 (3)	0.66974 (14)	0.0504 (9)
C5	0.80840 (16)	1.1006 (3)	0.68128 (12)	0.0434 (8)
C6	0.77027 (17)	1.0762 (3)	0.75298 (13)	0.0549 (9)
C7	0.91986 (18)	1.3147 (3)	0.59955 (15)	0.0606 (10)
C8	0.89532 (17)	1.1653 (4)	0.54362 (13)	0.0589 (9)
C9	0.82579 (17)	0.9788 (3)	0.55419 (13)	0.0495 (9)
C10	0.78023 (16)	0.9449 (3)	0.62117 (12)	0.0413 (8)
C11	0.70303 (15)	0.7611 (3)	0.63076 (11)	0.0436 (7)
C12	0.56648 (16)	0.2867 (3)	0.54520 (12)	0.0398 (8)
C13	0.46509 (18)	0.2336 (3)	0.64613 (12)	0.0503 (9)
C14	0.53798 (18)	0.4406 (3)	0.66051 (11)	0.0496 (8)
H1	0.76960	1.21310	0.85380	0.0800*
H2	0.87910	1.52400	0.83260	0.0850*
H3	0.94840	1.56920	0.71970	0.0750*
H3N	0.4590 (16)	0.028 (3)	0.5590 (11)	0.065 (7)*
H4	0.76770	0.73180	0.50630	0.0970*
H6	0.72670	0.95210	0.76300	0.0660*
H7	0.96540	1.43790	0.59150	0.0730*
H8	0.92460	1.18630	0.49810	0.0710*
H11	0.67310	0.74520	0.67630	0.0520*
H14A	0.48920	0.57040	0.66440	0.0600*
H14B	0.59220	0.42690	0.70580	0.0600*

	U11	U22	U33	U12	U13	U23
O1	0.0538 (10)	0.0529 (8)	0.0415 (10)	−0.0044 (7)	0.0094 (8)	−0.0084 (7)
O2	0.0901 (13)	0.0776 (10)	0.0488 (11)	−0.0257 (9)	0.0233 (9)	0.0057 (9)
O3	0.0725 (12)	0.0686 (10)	0.0544 (11)	−0.0094 (8)	0.0156 (9)	−0.0054 (9)
N1	0.0401 (10)	0.0373 (9)	0.0473 (12)	−0.0016 (8)	0.0000 (9)	−0.0017 (9)
N2	0.0467 (11)	0.0387 (10)	0.0424 (12)	−0.0071 (9)	0.0067 (9)	−0.0046 (9)
N3	0.0522 (12)	0.0420 (11)	0.0421 (13)	−0.0091 (9)	0.0061 (10)	−0.0013 (10)
C1	0.0649 (16)	0.0670 (16)	0.0662 (18)	−0.0015 (14)	0.0014 (14)	−0.0187 (14)
C2	0.0648 (18)	0.0583 (16)	0.083 (2)	0.0033 (13)	−0.0137 (16)	−0.0216 (15)
C3	0.0477 (15)	0.0391 (13)	0.095 (2)	−0.0026 (11)	−0.0162 (15)	−0.0068 (15)
C4	0.0383 (14)	0.0375 (13)	0.0718 (18)	0.0023 (11)	−0.0083 (12)	0.0001 (13)
C5	0.0343 (12)	0.0361 (12)	0.0576 (16)	0.0059 (10)	−0.0042 (11)	−0.0009 (11)
C6	0.0523 (15)	0.0508 (14)	0.0602 (17)	−0.0031 (11)	0.0014 (13)	−0.0107 (13)
C7	0.0455 (15)	0.0441 (14)	0.090 (2)	−0.0063 (11)	−0.0017 (15)	0.0105 (14)
C8	0.0478 (14)	0.0590 (15)	0.0704 (18)	−0.0027 (12)	0.0097 (13)	0.0143 (14)
C9	0.0432 (14)	0.0457 (13)	0.0586 (17)	0.0027 (11)	0.0013 (12)	−0.0004 (12)
C10	0.0328 (12)	0.0372 (12)	0.0532 (15)	−0.0012 (10)	0.0017 (11)	0.0029 (11)
C11	0.0457 (13)	0.0405 (11)	0.0441 (14)	0.0024 (11)	0.0037 (11)	−0.0020 (11)
C12	0.0377 (13)	0.0386 (13)	0.0417 (14)	0.0016 (10)	−0.0010 (11)	0.0013 (11)
C13	0.0601 (16)	0.0494 (14)	0.0406 (15)	−0.0026 (12)	0.0029 (12)	0.0028 (12)
C14	0.0585 (15)	0.0488 (13)	0.0410 (14)	−0.0022 (11)	0.0036 (12)	−0.0052 (10)

O1—C12	1.219 (3)	C5—C10	1.440 (3)
O2—C13	1.209 (3)	C5—C6	1.419 (3)
O3—C9	1.361 (3)	C7—C8	1.355 (3)
O3—H4	0.8200	C8—C9	1.405 (3)
N1—N2	1.3726 (19)	C9—C10	1.385 (3)
N1—C11	1.293 (2)	C10—C11	1.443 (3)
N2—C12	1.357 (2)	C13—C14	1.508 (3)
N2—C14	1.451 (3)	C1—H1	0.9300
N3—C13	1.362 (3)	C2—H2	0.9300
N3—C12	1.389 (3)	C3—H3	0.9300
N3—H3N	0.890 (18)	C6—H6	0.9300
C1—C6	1.366 (3)	C7—H7	0.9300
C1—C2	1.389 (3)	C8—H8	0.9300
C2—C3	1.360 (4)	C11—H11	0.9300
C3—C4	1.413 (3)	C14—H14A	0.9700
C4—C7	1.413 (4)	C14—H14B	0.9700
C4—C5	1.416 (3)
C9—O3—H4	109.00	N2—C12—N3	106.33 (17)
N2—N1—C11	116.51 (16)	O1—C12—N2	127.76 (17)
N1—N2—C14	125.77 (14)	O1—C12—N3	125.91 (18)
C12—N2—C14	112.17 (15)	O2—C13—N3	126.88 (18)
N1—N2—C12	121.80 (16)	O2—C13—C14	126.97 (19)
C12—N3—C13	113.02 (17)	N3—C13—C14	106.15 (17)
C13—N3—H3N	123.1 (13)	N2—C14—C13	102.24 (15)
C12—N3—H3N	123.7 (13)	C2—C1—H1	119.00
C2—C1—C6	121.3 (2)	C6—C1—H1	119.00
C1—C2—C3	119.5 (2)	C1—C2—H2	120.00
C2—C3—C4	121.1 (2)	C3—C2—H2	120.00
C3—C4—C5	119.8 (2)	C2—C3—H3	119.00
C3—C4—C7	121.57 (18)	C4—C3—H3	119.00
C5—C4—C7	118.64 (19)	C1—C6—H6	119.00
C4—C5—C10	119.44 (19)	C5—C6—H6	119.00
C4—C5—C6	117.23 (19)	C4—C7—H7	119.00
C6—C5—C10	123.33 (17)	C8—C7—H7	119.00
C1—C6—C5	121.07 (18)	C7—C8—H8	120.00
C4—C7—C8	121.78 (19)	C9—C8—H8	120.00
C7—C8—C9	120.2 (2)	N1—C11—H11	119.00
C8—C9—C10	121.05 (19)	C10—C11—H11	119.00
O3—C9—C10	123.12 (17)	N2—C14—H14A	111.00
O3—C9—C8	115.82 (19)	N2—C14—H14B	111.00
C5—C10—C9	118.88 (17)	C13—C14—H14A	111.00
C5—C10—C11	119.83 (18)	C13—C14—H14B	111.00
C9—C10—C11	121.27 (18)	H14A—C14—H14B	109.00
N1—C11—C10	122.37 (18)
C11—N1—N2—C12	−177.23 (16)	C7—C4—C5—C10	−1.2 (3)
C11—N1—N2—C14	9.1 (2)	C3—C4—C7—C8	−179.6 (2)
N2—N1—C11—C10	−179.57 (16)	C5—C4—C7—C8	−0.2 (3)
N1—N2—C12—O1	2.8 (3)	C4—C5—C6—C1	2.3 (3)
N1—N2—C12—N3	−177.61 (15)	C10—C5—C6—C1	−178.07 (19)
C14—N2—C12—O1	177.26 (19)	C4—C5—C10—C9	2.3 (3)
C14—N2—C12—N3	−3.1 (2)	C4—C5—C10—C11	−175.93 (17)
N1—N2—C14—C13	176.87 (16)	C6—C5—C10—C9	−177.34 (18)
C12—N2—C14—C13	2.7 (2)	C6—C5—C10—C11	4.4 (3)
C13—N3—C12—O1	−178.02 (19)	C4—C7—C8—C9	0.6 (3)
C13—N3—C12—N2	2.4 (2)	C7—C8—C9—O3	179.31 (19)
C12—N3—C13—O2	179.8 (2)	C7—C8—C9—C10	0.6 (3)
C12—N3—C13—C14	−0.7 (2)	O3—C9—C10—C5	179.36 (17)
C6—C1—C2—C3	−0.7 (3)	O3—C9—C10—C11	−2.4 (3)
C2—C1—C6—C5	−0.9 (3)	C8—C9—C10—C5	−2.1 (3)
C1—C2—C3—C4	0.8 (3)	C8—C9—C10—C11	176.19 (18)
C2—C3—C4—C5	0.7 (3)	C5—C10—C11—N1	179.33 (17)
C2—C3—C4—C7	−179.9 (2)	C9—C10—C11—N1	1.1 (3)
C3—C4—C5—C6	−2.2 (3)	O2—C13—C14—N2	178.40 (19)
C3—C4—C5—C10	178.15 (18)	N3—C13—C14—N2	−1.1 (2)
C7—C4—C5—C6	178.47 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1i	0.890 (18)	1.962 (18)	2.851 (2)	177.9 (19)
O3—H4···N1	0.82	1.91	2.622 (2)	145
C6—H6···O2ii	0.93	2.55	3.469 (2)	169
C14—H14B···O2ii	0.97	2.36	3.038 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1i	0.890 (18)	1.962 (18)	2.851 (2)	177.9 (19)
O3—H4⋯N1	0.82	1.91	2.622 (2)	145
C6—H6⋯O2ii	0.93	2.55	3.469 (2)	169
C14—H14B⋯O2ii	0.97	2.36	3.038 (2)	127

Symmetry codes: (i) ; (ii) .