Methyl 3-[(E)-(2-hy-droxy-1-naphth-yl)methyl-idene]carbazate.

The title compound, C(13)H(12)N(2)O(3), has an E configuration with respect to the C=N bond: the conformation is stabilized by an intramolecular O-H⋯N hydrogen bond. In the crystal, an N-H⋯O interaction links the molecules into a C(4) chain along [100].

Related literature

For the naphthalene group as a fluoro­phore, see: Li et al. (2010 ▶); Iijima et al. (2010 ▶). For a related structure and bond length, see: Xu et al. (2009 ▶). For the synthetic method, see: Zhang et al. (1999 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For applications of Schiff base–metal complexes, see: Cozzi (2004 ▶).

Experimental

Crystal data

C13H12N2O3

M = 244.25

Orthorhombic,

a = 5.1754 (3) Å

b = 9.2787 (5) Å

c = 23.6766 (12) Å

V = 1136.97 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 291 K

0.40 × 0.36 × 0.30 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.960, T max = 0.970

6329 measured reflections

1562 independent reflections

1120 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.058

S = 1.09

1562 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.13 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044041/bx2318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044041/bx2318Isup2.hkl

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

C13H12N2O3	F(000) = 512
Mr = 244.25	Dx = 1.427 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2986 reflections
a = 5.1754 (3) Å	θ = 3.4–29.1°
b = 9.2787 (5) Å	µ = 0.10 mm−1
c = 23.6766 (12) Å	T = 291 K
V = 1136.97 (11) Å3	Block, yellow
Z = 4	0.40 × 0.36 × 0.30 mm

Oxford Diffraction Gemini S Ultra diffractometer	1562 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1120 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 15.9149 pixels mm-1	θmax = 27.9°, θmin = 3.4°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.960, Tmax = 0.970	l = −30→29
6329 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0239P)2] where P = (Fo2 + 2Fc2)/3
1562 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Experimental. Absorption correction: CrysAlisPro,(Oxford Diffraction 2009). Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.7358 (4)	0.2360 (2)	0.64442 (8)	0.0492 (5)
H1A	0.8342	0.2851	0.6711	0.059*
C2	0.7869 (4)	0.2539 (2)	0.58880 (8)	0.0538 (5)
H2A	0.9175	0.3163	0.5774	0.065*
C3	0.6428 (4)	0.1785 (2)	0.54858 (8)	0.0529 (5)
H3	0.6800	0.1901	0.5104	0.064*
C4	0.4483 (4)	0.0881 (2)	0.56460 (7)	0.0460 (5)
H4	0.3539	0.0397	0.5371	0.055*
C5	0.3871 (3)	0.06633 (18)	0.62220 (7)	0.0363 (4)
C6	0.5348 (3)	0.14347 (18)	0.66256 (7)	0.0402 (4)
C7	0.4774 (4)	0.1259 (2)	0.72052 (7)	0.0478 (5)
H7	0.5710	0.1780	0.7471	0.057*
C8	0.2899 (4)	0.0355 (2)	0.73821 (7)	0.0476 (5)
H8	0.2564	0.0256	0.7766	0.057*
C9	0.1459 (3)	−0.04352 (19)	0.69896 (7)	0.0406 (4)
C10	0.1867 (3)	−0.02866 (18)	0.64118 (7)	0.0354 (4)
C11	0.0239 (3)	−0.10114 (18)	0.60072 (6)	0.0396 (4)
H11	0.0471	−0.0813	0.5626	0.047*
C12	−0.4938 (4)	−0.33819 (19)	0.57803 (6)	0.0397 (4)
C13	−0.7307 (4)	−0.4828 (2)	0.64025 (8)	0.0554 (5)
H13A	−0.8917	−0.4395	0.6294	0.083*
H13B	−0.7372	−0.5087	0.6795	0.083*
H13C	−0.7014	−0.5677	0.6179	0.083*
N1	−0.1522 (3)	−0.19204 (16)	0.61512 (6)	0.0410 (4)
N2	−0.2962 (3)	−0.24594 (17)	0.57083 (5)	0.0455 (4)
H2	−0.2578	−0.2193	0.5371	0.055*
O1	−0.0360 (3)	−0.13205 (14)	0.72081 (5)	0.0553 (4)
H1	−0.1165	−0.1705	0.6951	0.083*
O2	−0.6293 (2)	−0.37715 (15)	0.53872 (5)	0.0548 (4)
O3	−0.5234 (2)	−0.38178 (12)	0.63113 (4)	0.0462 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (11)	0.0476 (11)	0.0551 (11)	−0.0007 (12)	−0.0054 (9)	−0.0056 (10)
C2	0.0448 (11)	0.0570 (12)	0.0597 (12)	−0.0065 (12)	0.0032 (11)	0.0074 (11)
C3	0.0487 (12)	0.0657 (14)	0.0443 (10)	−0.0078 (12)	−0.0017 (10)	0.0070 (10)
C4	0.0413 (11)	0.0562 (12)	0.0404 (9)	−0.0019 (11)	−0.0027 (9)	0.0043 (9)
C5	0.0347 (9)	0.0353 (9)	0.0388 (9)	0.0067 (9)	−0.0037 (8)	0.0020 (8)
C6	0.0385 (10)	0.0368 (10)	0.0453 (9)	0.0044 (11)	−0.0051 (9)	0.0009 (9)
C7	0.0546 (11)	0.0499 (11)	0.0390 (9)	−0.0025 (13)	−0.0065 (10)	−0.0068 (9)
C8	0.0570 (12)	0.0542 (12)	0.0315 (9)	0.0008 (12)	−0.0029 (9)	−0.0013 (9)
C9	0.0406 (10)	0.0410 (10)	0.0404 (10)	0.0028 (10)	−0.0001 (9)	0.0058 (9)
C10	0.0359 (10)	0.0358 (9)	0.0346 (9)	0.0044 (10)	−0.0040 (8)	0.0002 (8)
C11	0.0401 (10)	0.0427 (10)	0.0359 (9)	0.0007 (12)	0.0000 (8)	0.0025 (8)
C12	0.0427 (10)	0.0428 (10)	0.0336 (9)	0.0023 (11)	−0.0029 (9)	−0.0007 (8)
C13	0.0492 (12)	0.0622 (12)	0.0547 (11)	−0.0121 (13)	−0.0041 (10)	0.0117 (10)
N1	0.0422 (9)	0.0446 (9)	0.0362 (7)	−0.0021 (9)	−0.0076 (7)	−0.0017 (7)
N2	0.0503 (9)	0.0556 (9)	0.0305 (7)	−0.0110 (10)	−0.0022 (7)	0.0015 (7)
O1	0.0580 (8)	0.0671 (9)	0.0406 (6)	−0.0135 (9)	0.0007 (7)	0.0059 (7)
O2	0.0601 (8)	0.0684 (9)	0.0360 (6)	−0.0118 (9)	−0.0126 (6)	0.0004 (7)
O3	0.0506 (7)	0.0528 (7)	0.0352 (6)	−0.0126 (8)	−0.0053 (6)	0.0075 (6)

C1—C2	1.353 (2)	C9—O1	1.3523 (19)
C1—C6	1.416 (2)	C9—C10	1.391 (2)
C1—H1A	0.9300	C10—C11	1.442 (2)
C2—C3	1.397 (3)	C11—N1	1.288 (2)
C2—H2A	0.9300	C11—H11	0.9300
C3—C4	1.364 (2)	C12—O2	1.2203 (19)
C3—H3	0.9300	C12—O3	1.3294 (19)
C4—C5	1.414 (2)	C12—N2	1.344 (2)
C4—H4	0.9300	C13—O3	1.441 (2)
C5—C6	1.418 (2)	C13—H13A	0.9600
C5—C10	1.433 (2)	C13—H13B	0.9600
C6—C7	1.413 (2)	C13—H13C	0.9600
C7—C8	1.350 (2)	N1—N2	1.3804 (18)
C7—H7	0.9300	N2—H2	0.8600
C8—C9	1.399 (2)	O1—H1	0.8200
C8—H8	0.9300
C2—C1—C6	120.88 (18)	O1—C9—C10	122.83 (16)
C2—C1—H1A	119.6	O1—C9—C8	115.79 (15)
C6—C1—H1A	119.6	C10—C9—C8	121.38 (17)
C1—C2—C3	119.82 (19)	C9—C10—C5	118.63 (16)
C1—C2—H2A	120.1	C9—C10—C11	121.23 (16)
C3—C2—H2A	120.1	C5—C10—C11	120.08 (14)
C4—C3—C2	120.82 (17)	N1—C11—C10	122.89 (14)
C4—C3—H3	119.6	N1—C11—H11	118.6
C2—C3—H3	119.6	C10—C11—H11	118.6
C3—C4—C5	121.39 (17)	O2—C12—O3	124.41 (18)
C3—C4—H4	119.3	O2—C12—N2	121.93 (15)
C5—C4—H4	119.3	O3—C12—N2	113.66 (15)
C4—C5—C6	117.21 (16)	O3—C13—H13A	109.5
C4—C5—C10	123.50 (16)	O3—C13—H13B	109.5
C6—C5—C10	119.29 (15)	H13A—C13—H13B	109.5
C7—C6—C1	121.25 (17)	O3—C13—H13C	109.5
C7—C6—C5	118.88 (17)	H13A—C13—H13C	109.5
C1—C6—C5	119.87 (15)	H13B—C13—H13C	109.5
C8—C7—C6	121.60 (17)	C11—N1—N2	114.73 (13)
C8—C7—H7	119.2	C12—N2—N1	123.02 (13)
C6—C7—H7	119.2	C12—N2—H2	118.5
C7—C8—C9	120.18 (16)	N1—N2—H2	118.5
C7—C8—H8	119.9	C9—O1—H1	109.5
C9—C8—H8	119.9	C12—O3—C13	115.17 (14)
C6—C1—C2—C3	−1.1 (3)	C5—C10—C9—O1	−179.05 (14)
C1—C2—C3—C4	0.9 (3)	C5—C10—C9—C8	2.1 (2)
C5—C4—C3—C2	−0.6 (3)	C11—C10—C9—O1	4.0 (3)
C6—C5—C4—C3	0.6 (3)	C11—C10—C9—C8	−174.82 (16)
C10—C5—C4—C3	−179.27 (16)	C9—C10—C5—C4	178.98 (18)
C2—C1—C6—C7	−178.94 (18)	C9—C10—C5—C6	−0.9 (2)
C2—C1—C6—C5	1.1 (3)	C11—C10—C5—C4	−4.0 (2)
C4—C5—C6—C7	179.26 (17)	C11—C10—C5—C6	176.13 (15)
C10—C5—C6—C7	−0.9 (2)	C9—C10—C11—N1	−6.0 (2)
C4—C5—C6—C1	−0.8 (2)	C5—C10—C11—N1	177.12 (14)
C10—C5—C6—C1	179.04 (15)	N2—N1—C11—C10	177.35 (15)
C1—C6—C7—C8	−178.46 (16)	N1—N2—C12—O2	175.09 (16)
C5—C6—C7—C8	1.5 (3)	N1—N2—C12—O3	−5.3 (2)
C9—C8—C7—C6	−0.2 (3)	C12—N2—N1—C11	−177.71 (15)
C7—C8—C9—O1	179.49 (16)	C13—O3—C12—O2	0.6 (3)
C7—C8—C9—C10	−1.6 (3)	C13—O3—C12—N2	−178.95 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.91	2.6332 (18)	146
N2—H2···O2i	0.86	2.11	2.9626 (18)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.91	2.6332 (18)	146
N2—H2⋯O2i	0.86	2.11	2.9626 (18)	170

Symmetry code: (i) .