N-(4-Amino-phen-yl)-1,8-naphthalimide hemihydrate.

The title compound, C(18)H(12)N(2)O(2)·0.5H(2)O, was prepared by the reaction of 1,4-phenyl-enediamine with 1,8-naphthalic anhydride in refluxing dimethyl-formamide. The structure is stabilized by N-H⋯O and O-H⋯O hydrogen bonds. There are π-π stacking inter-actions [centroid-centroid distances of 3.718 (2), 3.510 (2) and 3.546 (2) Å] and C-H⋯π inter-actions between the mol-ecules. The water molecule lies on a twofold rotation axis. Its two H atoms are disordered equally over two positions.

Related literature

For related literature, see: Ofir (2006 ▶); Cederfur et al. (2003 ▶); Lavin & Shimizu (2006 ▶).

Experimental

Crystal data

C18H12N2O2·0.5H2O

M = 297.31

Orthorhombic,

a = 22.926 (5) Å

b = 17.930 (4) Å

c = 6.836 (1) Å

V = 2810 (1) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.40 × 0.40 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

5656 measured reflections

1359 independent reflections

1308 reflections with I > 2σ(I)

R int = 0.027

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.164

S = 1.33

1359 reflections

204 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 1990 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706583X/ez2108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706583X/ez2108Isup2.hkl

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

C18H12N2O2·0.5H2O	Dx = 1.406 Mg m−3
Mr = 297.31	Melting point: 286 K
Orthorhombic, Aba2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: A2 -2ac	Cell parameters from 512 reflections
a = 22.926 (5) Å	θ = 2–22º
b = 17.930 (4) Å	µ = 0.10 mm−1
c = 6.836 (1) Å	T = 295 (2) K
V = 2810 (1) Å3	Block, yellow
Z = 8	0.40 × 0.40 × 0.20 mm
F000 = 1240

Enraf–Nonius CAD-4 diffractometer	Rint = 0.027
Radiation source: fine-focus sealed tube	θmax = 25.0º
Monochromator: graphite	θmin = 2.3º
T = 295(2) K	h = −27→23
ω scans	k = −20→21
Absorption correction: none	l = −8→7
5656 measured reflections	3 standard reflections
1359 independent reflections	every 200 reflections
1308 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069	H-atom parameters constrained
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.062P)2 + 2.2916P] where P = (Fo2 + 2Fc2)/3
S = 1.33	(Δ/σ)max < 0.001
1359 reflections	Δρmax = 0.24 e Å−3
204 parameters	Δρmin = −0.21 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
O1	0.42928 (16)	0.07821 (19)	0.8275 (7)	0.0704 (12)
O2	0.27279 (15)	0.22571 (18)	0.9326 (8)	0.0675 (12)
N1	0.35109 (17)	0.15181 (19)	0.8761 (6)	0.0447 (10)
N2	0.4972 (2)	0.3999 (3)	0.9511 (11)	0.095 (2)
H2A	0.5002	0.4314	0.8566	0.115*
H2B	0.5170	0.4064	1.0567	0.115*
C1	0.2903 (2)	0.1646 (3)	0.8953 (8)	0.0502 (13)
C2	0.2527 (2)	0.0997 (2)	0.8651 (7)	0.0481 (12)
C3	0.1932 (2)	0.1090 (3)	0.8646 (8)	0.0609 (15)
H3A	0.1772	0.1563	0.8800	0.073*
C4	0.1569 (3)	0.0475 (4)	0.8411 (10)	0.080 (2)
H4A	0.1167	0.0543	0.8394	0.096*
C5	0.1787 (3)	−0.0214 (4)	0.8208 (10)	0.080 (2)
H5A	0.1533	−0.0616	0.8090	0.096*
C6	0.2396 (3)	−0.0341 (3)	0.8168 (9)	0.0641 (16)
C7	0.2649 (4)	−0.1041 (3)	0.7944 (10)	0.082 (2)
H7A	0.2409	−0.1457	0.7839	0.099*
C8	0.3234 (4)	−0.1134 (3)	0.7875 (11)	0.083 (2)
H8A	0.3391	−0.1610	0.7732	0.100*
C9	0.3604 (3)	−0.0517 (3)	0.8017 (9)	0.0669 (16)
H9A	0.4005	−0.0581	0.7927	0.080*
C10	0.3376 (3)	0.0183 (3)	0.8289 (8)	0.0538 (13)
C11	0.2765 (2)	0.0281 (3)	0.8369 (8)	0.0509 (12)
C12	0.3765 (2)	0.0826 (2)	0.8410 (8)	0.0512 (13)
C13	0.3889 (2)	0.2158 (3)	0.8965 (9)	0.0522 (14)
C14	0.4212 (2)	0.2260 (3)	1.0623 (10)	0.0602 (15)
H14A	0.4190	0.1914	1.1632	0.072*
C15	0.4569 (3)	0.2869 (3)	1.0813 (11)	0.0629 (15)
H15A	0.4787	0.2932	1.1949	0.075*
C16	0.4609 (2)	0.3390 (3)	0.9330 (10)	0.0577 (14)
C17	0.4289 (2)	0.3279 (3)	0.7643 (9)	0.0565 (14)
H17A	0.4319	0.3619	0.6619	0.068*
C18	0.3928 (2)	0.2670 (3)	0.7466 (9)	0.0544 (14)
H18A	0.3710	0.2603	0.6332	0.065*
O1W	0.5000	0.0000	0.0917 (13)	0.089 (2)
H1W1	0.4830	0.0421	0.0966	0.107*	0.50
H2W1	0.5239	0.0012	−0.0033	0.107*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.055 (2)	0.063 (2)	0.094 (3)	0.0129 (17)	0.011 (3)	0.010 (2)
O2	0.067 (2)	0.0447 (18)	0.091 (3)	0.0124 (16)	−0.001 (3)	0.000 (2)
N1	0.053 (2)	0.0357 (18)	0.046 (2)	−0.0006 (16)	−0.004 (2)	0.0032 (18)
N2	0.102 (4)	0.079 (3)	0.106 (5)	−0.039 (3)	−0.022 (4)	0.011 (4)
C1	0.055 (3)	0.045 (2)	0.050 (3)	0.009 (2)	−0.003 (3)	0.005 (2)
C2	0.055 (3)	0.055 (2)	0.034 (3)	−0.004 (2)	−0.004 (2)	0.010 (2)
C3	0.063 (3)	0.078 (4)	0.042 (3)	−0.004 (3)	−0.004 (3)	0.009 (3)
C4	0.065 (4)	0.116 (5)	0.060 (4)	−0.028 (4)	−0.001 (3)	0.021 (4)
C5	0.097 (5)	0.087 (4)	0.056 (4)	−0.044 (4)	−0.012 (4)	0.018 (4)
C6	0.090 (5)	0.059 (3)	0.043 (3)	−0.027 (3)	−0.005 (3)	0.013 (3)
C7	0.136 (7)	0.052 (3)	0.058 (4)	−0.030 (4)	−0.018 (4)	0.013 (3)
C8	0.142 (7)	0.042 (3)	0.065 (4)	0.002 (4)	−0.006 (5)	−0.001 (3)
C9	0.102 (4)	0.047 (3)	0.052 (4)	0.008 (3)	0.001 (3)	0.001 (3)
C10	0.079 (4)	0.037 (2)	0.045 (3)	0.003 (2)	0.006 (3)	0.011 (2)
C11	0.072 (3)	0.048 (3)	0.032 (2)	−0.007 (2)	−0.002 (3)	0.008 (2)
C12	0.060 (3)	0.043 (3)	0.050 (3)	0.010 (2)	0.001 (3)	0.007 (2)
C13	0.053 (3)	0.038 (2)	0.066 (4)	0.004 (2)	0.001 (3)	0.004 (3)
C14	0.063 (3)	0.055 (3)	0.063 (4)	−0.002 (3)	−0.015 (3)	0.012 (3)
C15	0.061 (3)	0.058 (3)	0.071 (4)	−0.006 (3)	−0.016 (3)	−0.003 (3)
C16	0.053 (3)	0.045 (3)	0.075 (4)	−0.007 (2)	0.000 (3)	−0.007 (3)
C17	0.067 (3)	0.039 (2)	0.063 (4)	−0.003 (2)	−0.006 (3)	0.012 (3)
C18	0.059 (3)	0.044 (3)	0.060 (4)	0.000 (2)	−0.007 (3)	0.001 (3)
O1W	0.098 (5)	0.093 (4)	0.078 (4)	0.028 (4)	0.000	0.000

O1—C12	1.217 (6)	C7—H7A	0.9300
O2—C1	1.194 (6)	C8—C9	1.397 (9)
N1—C12	1.391 (6)	C8—H8A	0.9300
N1—C1	1.419 (6)	C9—C10	1.372 (7)
N1—C13	1.445 (6)	C9—H9A	0.9300
N2—C16	1.379 (6)	C10—C11	1.413 (7)
N2—H2A	0.8600	C10—C12	1.461 (7)
N2—H2B	0.8600	C13—C14	1.366 (8)
C1—C2	1.462 (7)	C13—C18	1.379 (7)
C2—C3	1.375 (8)	C14—C15	1.371 (7)
C2—C11	1.408 (7)	C14—H14A	0.9300
C3—C4	1.391 (8)	C15—C16	1.381 (8)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.340 (9)	C16—C17	1.381 (8)
C4—H4A	0.9300	C17—C18	1.375 (7)
C5—C6	1.416 (9)	C17—H17A	0.9300
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.391 (8)	O1W—H1W1	0.8501
C6—C11	1.406 (6)	O1W—H2W1	0.8501
C7—C8	1.353 (10)
C12—N1—C1	124.8 (4)	C10—C9—H9A	119.9
C12—N1—C13	118.3 (4)	C8—C9—H9A	119.9
C1—N1—C13	116.9 (4)	C9—C10—C11	119.8 (5)
C16—N2—H2A	120.0	C9—C10—C12	119.8 (5)
C16—N2—H2B	120.0	C11—C10—C12	120.3 (4)
H2A—N2—H2B	120.0	C6—C11—C2	120.3 (5)
O2—C1—N1	119.8 (4)	C6—C11—C10	119.5 (5)
O2—C1—C2	124.2 (5)	C2—C11—C10	120.2 (5)
N1—C1—C2	115.9 (4)	O1—C12—N1	119.2 (4)
C3—C2—C11	119.6 (5)	O1—C12—C10	123.5 (4)
C3—C2—C1	119.2 (5)	N1—C12—C10	117.3 (4)
C11—C2—C1	121.1 (5)	C14—C13—C18	119.5 (5)
C2—C3—C4	119.9 (6)	C14—C13—N1	120.8 (5)
C2—C3—H3A	120.1	C18—C13—N1	119.7 (5)
C4—C3—H3A	120.1	C13—C14—C15	120.6 (6)
C5—C4—C3	121.3 (6)	C13—C14—H14A	119.7
C5—C4—H4A	119.4	C15—C14—H14A	119.7
C3—C4—H4A	119.4	C14—C15—C16	120.5 (6)
C4—C5—C6	121.2 (6)	C14—C15—H15A	119.7
C4—C5—H5A	119.4	C16—C15—H15A	119.7
C6—C5—H5A	119.4	N2—C16—C17	120.6 (6)
C7—C6—C11	118.5 (6)	N2—C16—C15	120.6 (6)
C7—C6—C5	123.9 (6)	C17—C16—C15	118.8 (5)
C11—C6—C5	117.6 (5)	C18—C17—C16	120.4 (5)
C8—C7—C6	121.9 (6)	C18—C17—H17A	119.8
C8—C7—H7A	119.1	C16—C17—H17A	119.8
C6—C7—H7A	119.1	C17—C18—C13	120.2 (5)
C7—C8—C9	120.1 (6)	C17—C18—H18A	119.9
C7—C8—H8A	120.0	C13—C18—H18A	119.9
C9—C8—H8A	120.0	H1W1—O1W—H2W1	107.7
C10—C9—C8	120.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1Wi	0.86	2.19	3.046 (6)	172
N2—H2B···O1ii	0.86	2.24	3.099 (5)	178
O1W—H1W1···O1iii	0.85	2.30	2.800 (5)	118
O1W—H2W1···O1iv	0.85	2.12	2.800 (5)	136
C15—H15A···Cg1v	0.93	2.96	.	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring C13–C18.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1Wi	0.86	2.19	3.046 (6)	172
N2—H2B⋯O1ii	0.86	2.24	3.099 (5)	178
O1W—H1W1⋯O1iii	0.85	2.30	2.800 (5)	118
O1W—H2W1⋯O1iv	0.85	2.12	2.800 (5)	136
C15—H15A⋯Cg1v	0.93	2.96	3.717	140

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