N-(2-Hydroxy­benzyl­ideneamino)-1,8-naphthalimide

The title compound, C₁₉H₁₂N₂O₃, was prepared by the reaction of hydrazine and salicylaldehyde with 1,8-naphthoic anhydride in refluxing dimethyl­formamide. The structure is stabilized by an intra­molecular O—H...N hydrogen bond and the crystal packing exhibits C—H...O hydrogen bonds. The dihedral angle formed by the benzene and naphthalimide systems is 175.9°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.060
• wR factor = 0.175
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

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Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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S1. Comment

1,8-Naphthlimide derivatives are an important class of compounds. 1,8-Naphthalimides exhibit hydrogen-bonding (Niemz et al., 1997) and cation-dependent (Poteau et al., 2000; De Silva et al., 1996) fluorescence.

In the title compound, the bond lengths and angles are normal (Ofir et al., 2006). The bond lengths of two C═O are little different, with 1.212 (4) Å for C19—O1 and 1.208 (4) Å for C8–02, respectively. The dihedral angle formed by the phenyl ring and naphthalimide moiety is 80.6 (3)°. The molecular conformation is stabilized by a O—H···N hydrogen bond and the crystal packing shows, CH···O hydrogen bonds (Table 2).

Related literature

For related literature, see: Niemz & Rotello (1997); Ofir (2006); Poteau et al. (2000); De Silva et al. (1996).

S2. Experimental

The single crystals of the title compound were obtained by the reaction hydrazine (0.1 mmol), 1,8-naphthalic anhydride (0.1 mmol) with salicylaldehyde (0.1 mmol) in refluxing DMF. Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from a DMF solution at room temperature.

S3. Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H=0.93 Å, and with U_iso=1.2U_eq. The hydroxyl H atom was freely refined.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1990; software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. The molecular structure and atom-labeling scheme for the title compound, with displacement ellipsoids drawn at the 30% probability level.

N-(2-Hydroxybenzylideneamino)-1,8-naphthalimide

Crystal data

C19H12N2O3	F(000) = 656
Mr = 316.31	Dx = 1.466 Mg m^−3
Monoclinic, P21/c	Melting point: 220 K
Hall symbol: -P 2y bc	Mo Kα radiation, λ = 0.71073 Å
a = 11.285 (2) Å	θ = 0–25°
b = 18.310 (4) Å	µ = 0.10 mm^−1
c = 6.9540 (14) Å	T = 295 K
β = 94.39 (3)°	Block, yellow
V = 1432.7 (5) Å^3	0.30 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1873 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
phi and ω scans	h = −13→13
7451 measured reflections	k = −17→21
2526 independent reflections	l = −7→8

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 1.5868P] where P = (Fo^2 + 2Fc^2)/3
2526 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.21 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
O1	0.3228 (2)	0.20728 (13)	0.6655 (4)	0.0573 (7)
O2	0.0289 (2)	0.04509 (12)	0.7451 (4)	0.0676 (8)
O3	0.3368 (2)	−0.01677 (15)	0.4076 (4)	0.0571 (7)
N1	0.1751 (2)	0.12810 (13)	0.7147 (4)	0.0425 (7)
N2	0.2506 (3)	0.07138 (14)	0.6572 (4)	0.0485 (7)
C1	0.4126 (3)	−0.07501 (18)	0.9058 (6)	0.0518 (9)
H1A	0.3999	−0.0616	1.0316	0.062*
C2	0.4805 (3)	−0.1357 (2)	0.8730 (7)	0.0617 (11)
H2B	0.5136	−0.1633	0.9758	0.074*
C3	0.4986 (3)	−0.1551 (2)	0.6859 (7)	0.0597 (11)
H3B	0.5442	−0.1961	0.6635	0.072*
C4	0.4514 (3)	−0.11538 (19)	0.5336 (6)	0.0553 (10)
H4A	0.4651	−0.1294	0.4087	0.066*
C5	0.3827 (3)	−0.05398 (17)	0.5628 (6)	0.0447 (8)
C6	0.3629 (3)	−0.03349 (16)	0.7522 (5)	0.0430 (8)
C7	0.2908 (3)	0.02979 (17)	0.7936 (5)	0.0426 (8)
H7A	0.2743	0.0398	0.9199	0.051*
C8	0.0574 (3)	0.10867 (16)	0.7415 (5)	0.0423 (8)
C9	−0.0255 (3)	0.16947 (16)	0.7623 (4)	0.0372 (7)
C10	−0.1421 (3)	0.15537 (19)	0.7914 (5)	0.0476 (9)
H10A	−0.1687	0.1074	0.7969	0.057*
C11	−0.2206 (3)	0.2130 (2)	0.8128 (5)	0.0507 (9)
H11A	−0.2995	0.2030	0.8329	0.061*
C12	−0.1842 (3)	0.28320 (19)	0.8049 (5)	0.0451 (8)
H12A	−0.2383	0.3207	0.8196	0.054*
C13	−0.0651 (3)	0.30016 (16)	0.7746 (4)	0.0386 (7)
C14	−0.0231 (3)	0.37226 (17)	0.7648 (5)	0.0457 (8)
H14A	−0.0751	0.4109	0.7792	0.055*
C15	0.0915 (3)	0.38627 (17)	0.7348 (5)	0.0451 (8)
H15A	0.1174	0.4344	0.7297	0.054*
C16	0.1716 (3)	0.32912 (17)	0.7113 (5)	0.0416 (8)
H16A	0.2501	0.3395	0.6889	0.050*
C17	0.1350 (3)	0.25784 (16)	0.7212 (4)	0.0345 (7)
C18	0.0156 (3)	0.24226 (15)	0.7523 (4)	0.0323 (7)
C19	0.2195 (3)	0.19840 (16)	0.6968 (5)	0.0393 (7)
H3A	0.297 (5)	0.026 (3)	0.432 (8)	0.13 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0383 (13)	0.0475 (15)	0.087 (2)	0.0010 (11)	0.0099 (13)	−0.0127 (13)
O2	0.0728 (18)	0.0271 (13)	0.106 (2)	−0.0027 (12)	0.0247 (16)	−0.0003 (13)
O3	0.0655 (17)	0.0497 (16)	0.0564 (17)	0.0107 (13)	0.0056 (13)	−0.0027 (13)
N1	0.0478 (16)	0.0285 (14)	0.0520 (17)	0.0096 (12)	0.0091 (13)	−0.0012 (12)
N2	0.0565 (18)	0.0345 (15)	0.0550 (19)	0.0149 (13)	0.0073 (14)	−0.0033 (13)
C1	0.0470 (19)	0.045 (2)	0.062 (2)	0.0022 (16)	−0.0014 (17)	0.0040 (18)
C2	0.044 (2)	0.044 (2)	0.095 (3)	0.0043 (16)	−0.007 (2)	0.011 (2)
C3	0.0362 (18)	0.0365 (19)	0.106 (4)	0.0048 (15)	0.005 (2)	−0.008 (2)
C4	0.0396 (18)	0.041 (2)	0.086 (3)	−0.0004 (16)	0.0107 (19)	−0.015 (2)
C5	0.0326 (16)	0.0341 (17)	0.068 (2)	−0.0033 (13)	0.0059 (16)	−0.0062 (16)
C6	0.0329 (16)	0.0300 (16)	0.066 (2)	−0.0019 (13)	0.0051 (15)	−0.0032 (15)
C7	0.0415 (17)	0.0335 (17)	0.053 (2)	0.0023 (14)	0.0025 (15)	−0.0044 (15)
C8	0.053 (2)	0.0287 (17)	0.046 (2)	0.0023 (14)	0.0090 (15)	0.0006 (14)
C9	0.0418 (17)	0.0329 (16)	0.0372 (18)	0.0002 (13)	0.0043 (14)	−0.0016 (13)
C10	0.051 (2)	0.0408 (19)	0.052 (2)	−0.0077 (16)	0.0110 (16)	0.0007 (16)
C11	0.0382 (18)	0.060 (2)	0.054 (2)	0.0011 (16)	0.0090 (16)	0.0023 (18)
C12	0.0426 (18)	0.049 (2)	0.0438 (19)	0.0119 (15)	0.0052 (15)	0.0028 (16)
C13	0.0423 (17)	0.0360 (17)	0.0369 (18)	0.0100 (14)	−0.0007 (14)	−0.0019 (14)
C14	0.052 (2)	0.0311 (17)	0.053 (2)	0.0129 (15)	−0.0020 (16)	−0.0036 (15)
C15	0.055 (2)	0.0258 (16)	0.053 (2)	−0.0012 (14)	−0.0073 (16)	−0.0031 (14)
C16	0.0412 (17)	0.0376 (18)	0.0450 (19)	−0.0043 (14)	−0.0032 (14)	−0.0025 (14)
C17	0.0361 (16)	0.0308 (16)	0.0356 (17)	0.0012 (12)	−0.0037 (13)	−0.0045 (13)
C18	0.0389 (16)	0.0294 (15)	0.0283 (15)	0.0016 (12)	−0.0002 (12)	−0.0009 (12)
C19	0.0401 (18)	0.0353 (17)	0.0416 (19)	0.0025 (14)	−0.0015 (14)	−0.0065 (14)

Geometric parameters (Å, º)

O1—C19	1.212 (4)	C8—C9	1.469 (4)
O2—C8	1.208 (4)	C9—C10	1.370 (4)
O3—C5	1.346 (4)	C9—C18	1.414 (4)
O3—H3A	0.92 (6)	C10—C11	1.393 (5)
N1—C19	1.391 (4)	C10—H10A	0.9300
N1—C8	1.401 (4)	C11—C12	1.352 (5)
N1—N2	1.420 (3)	C11—H11A	0.9300
N2—C7	1.273 (4)	C12—C13	1.410 (5)
C1—C2	1.379 (5)	C12—H12A	0.9300
C1—C6	1.394 (5)	C13—C14	1.406 (4)
C1—H1A	0.9300	C13—C18	1.414 (4)
C2—C3	1.378 (6)	C14—C15	1.350 (5)
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.360 (6)	C15—C16	1.401 (4)
C3—H3B	0.9300	C15—H15A	0.9300
C4—C5	1.389 (5)	C16—C17	1.372 (4)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.403 (5)	C17—C18	1.410 (4)
C6—C7	1.457 (4)	C17—C19	1.466 (4)
C7—H7A	0.9300
C5—O3—H3A	117 (4)	C18—C9—C8	119.7 (3)
C19—N1—C8	126.8 (2)	C9—C10—C11	119.9 (3)
C19—N1—N2	115.1 (3)	C9—C10—H10A	120.0
C8—N1—N2	116.5 (2)	C11—C10—H10A	120.0
C7—N2—N1	114.5 (3)	C12—C11—C10	121.2 (3)
C2—C1—C6	120.6 (4)	C12—C11—H11A	119.4
C2—C1—H1A	119.7	C10—C11—H11A	119.4
C6—C1—H1A	119.7	C11—C12—C13	120.8 (3)
C3—C2—C1	119.2 (4)	C11—C12—H12A	119.6
C3—C2—H2B	120.4	C13—C12—H12A	119.6
C1—C2—H2B	120.4	C14—C13—C12	122.9 (3)
C4—C3—C2	121.4 (3)	C14—C13—C18	118.4 (3)
C4—C3—H3B	119.3	C12—C13—C18	118.7 (3)
C2—C3—H3B	119.3	C15—C14—C13	121.1 (3)
C3—C4—C5	120.5 (4)	C15—C14—H14A	119.5
C3—C4—H4A	119.7	C13—C14—H14A	119.5
C5—C4—H4A	119.7	C14—C15—C16	120.7 (3)
O3—C5—C4	118.5 (3)	C14—C15—H15A	119.6
O3—C5—C6	122.6 (3)	C16—C15—H15A	119.6
C4—C5—C6	119.0 (3)	C17—C16—C15	120.3 (3)
C1—C6—C5	119.3 (3)	C17—C16—H16A	119.8
C1—C6—C7	118.7 (3)	C15—C16—H16A	119.8
C5—C6—C7	122.0 (3)	C16—C17—C18	119.7 (3)
N2—C7—C6	120.1 (3)	C16—C17—C19	119.9 (3)
N2—C7—H7A	120.0	C18—C17—C19	120.4 (3)
C6—C7—H7A	120.0	C17—C18—C13	119.8 (3)
O2—C8—N1	120.3 (3)	C17—C18—C9	121.2 (3)
O2—C8—C9	123.7 (3)	C13—C18—C9	119.0 (3)
N1—C8—C9	116.0 (3)	O1—C19—N1	119.9 (3)
C10—C9—C18	120.4 (3)	O1—C19—C17	124.4 (3)
C10—C9—C8	119.9 (3)	N1—C19—C17	115.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.91 (4)	1.88 (4)	2.612 (4)	134 (4)
C3—H3B···O1^i	0.93	2.55	3.341 (4)	143
C14—H14A···O2^ii	0.93	2.52	3.166 (4)	127

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2.