organic compounds
N-(4-Aminophenyl)-1,8-naphthalimide hemihydrate
aNew Materials and Functional Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
*Correspondence e-mail: ffj2003@163169.net
The title compound, C18H12N2O2·0.5H2O, was prepared by the reaction of 1,4-phenylenediamine with 1,8-naphthalic anhydride in refluxing dimethylformamide. The structure is stabilized by N—H⋯O and O—H⋯O hydrogen bonds. There are π–π stacking interactions [centroid-centroid distances of 3.718 (2), 3.510 (2) and 3.546 (2) Å] and C—H⋯π interactions between the molecules. 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
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Data collection
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell 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).
Supporting information
https://doi.org/10.1107/S160053680706583X/ez2108sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706583X/ez2108Isup2.hkl
The title compound was obtained by reaction of 1,4-phenylenediamine (0.1 mol) with 1,8-naphthalic anhydride (0.1 mol) in refluxing DMF (50 ml) for 4 h. Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from a DMF solution at room temperature.
The two hydrogen atoms in the water molecule were found to be disordered, each with 50% site occupancies. H atoms were fixed geometrically and allowed to ride on their attached atoms, with N—H=0.86, O—H=0.85, C—H=0.93 Å, and with Uiso=1.2Ueq. In the absence of significant
effects Friedel pairs have been merged.Recently combinatorial and high throughput stategies have emerged as efficient methods to prepare large numbers of potential receptors (Cederfur et al., 2003). Since the naphthyl group has the potential to be a good receptor (Lavin & Shimizu, 2006), we have studied 1,8-naphthalimide derivatives, such as the pure compound (I) described here.
In the title compound (Fig. 1), the bond lengths and angles in the 1,8-naphthalenedicarboximide group and benzene ring are normal (Ofir, 2006), including the two C?O bond lengths (Table 1). The dihedral angle formed by the benzene ring (C13—C18) and naphthalic ring (N1/C1—C12) is 72.5 (2)°.
The crystal packing is realised by N2—H2A···O1w, N2—H2B···O1, O1W—H11W···O1 and C7- H7A···O2 hydrogen bonds (Table 2 and Fig 2). C—H···π interactions exist between C15—H15A and Cg(1)i, the centroid of the benzene ring C13—C18 [symmetry code: (i) –X,1/2-Y,1/2+Z]. There are π-stacking interactions between the naphthylamide groups, with distances between ring centroids of 3.718 (2), 3.510 (2) and 3.546 (2) Å, for Cg(2)···Cg(3)ii, Cg(3)···Cg(2)iii and Cg(2)···Cg(4)ii, respectively [Cg(2) = C2—C6/C11, Cg(3) = C1—C2/N1/C10—C12, Cg(4)=C6—C11; symmetry codes: (ii) 1/2-X,Y,-1/2 + z; (iii) 1/2-X,Y,1/2 + z].
For related literature, see: Ofir (2006); Cederfur et al. (2003); Lavin & Shimizu (2006).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); 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).Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level. Only one of the disorder positions is shown for the water H atoms. | |
Fig. 2. The packing of (I), viewed down the c axis, showing one layer of molecules connected by N—H···O and O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted. |
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 = 2–22° |
b = 17.930 (4) Å | µ = 0.10 mm−1 |
c = 6.836 (1) Å | T = 295 K |
V = 2810 (1) Å3 | Block, yellow |
Z = 8 | 0.40 × 0.40 × 0.20 mm |
F(000) = 1240 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.027 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = −27→23 |
ω scans | k = −20→21 |
5656 measured reflections | l = −8→7 |
1359 independent reflections | 3 standard reflections every 200 reflections |
1308 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.33 | w = 1/[σ2(Fo2) + (0.062P)2 + 2.2916P] where P = (Fo2 + 2Fc2)/3 |
1359 reflections | (Δ/σ)max < 0.001 |
204 parameters | Δρmax = 0.24 e Å−3 |
1 restraint | Δρmin = −0.21 e Å−3 |
C18H12N2O2·0.5H2O | V = 2810 (1) Å3 |
Mr = 297.31 | Z = 8 |
Orthorhombic, Aba2 | Mo Kα radiation |
a = 22.926 (5) Å | µ = 0.10 mm−1 |
b = 17.930 (4) Å | T = 295 K |
c = 6.836 (1) Å | 0.40 × 0.40 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.027 |
5656 measured reflections | 3 standard reflections every 200 reflections |
1359 independent reflections | intensity decay: none |
1308 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.069 | 1 restraint |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.33 | Δρmax = 0.24 e Å−3 |
1359 reflections | Δρmin = −0.21 e Å−3 |
204 parameters |
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 |
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) −x+1, −y+1/2, z+1/2; (iii) x, y, z−1; (iv) −x+1, −y, z−1; (v) −x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H12N2O2·0.5H2O |
Mr | 297.31 |
Crystal system, space group | Orthorhombic, Aba2 |
Temperature (K) | 295 |
a, b, c (Å) | 22.926 (5), 17.930 (4), 6.836 (1) |
V (Å3) | 2810 (1) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5656, 1359, 1308 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.164, 1.33 |
No. of reflections | 1359 |
No. of parameters | 204 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.21 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1Wi | 0.86 | 2.19 | 3.046 (6) | 171.5 |
N2—H2B···O1ii | 0.86 | 2.24 | 3.099 (5) | 178.4 |
O1W—H1W1···O1iii | 0.85 | 2.30 | 2.800 (5) | 117.6 |
O1W—H2W1···O1iv | 0.85 | 2.12 | 2.800 (5) | 136.4 |
C15—H15A···Cg1v | 0.93 | 2.96 | . | 139.88 |
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) −x+1, −y+1/2, z+1/2; (iii) x, y, z−1; (iv) −x+1, −y, z−1; (v) −x, −y+1/2, z+1/2. |
Acknowledgements
The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2005B04).
References
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Recently combinatorial and high throughput stategies have emerged as efficient methods to prepare large numbers of potential receptors (Cederfur et al., 2003). Since the naphthyl group has the potential to be a good receptor (Lavin & Shimizu, 2006), we have studied 1,8-naphthalimide derivatives, such as the pure compound (I) described here.
In the title compound (Fig. 1), the bond lengths and angles in the 1,8-naphthalenedicarboximide group and benzene ring are normal (Ofir, 2006), including the two C?O bond lengths (Table 1). The dihedral angle formed by the benzene ring (C13—C18) and naphthalic ring (N1/C1—C12) is 72.5 (2)°.
The crystal packing is realised by N2—H2A···O1w, N2—H2B···O1, O1W—H11W···O1 and C7- H7A···O2 hydrogen bonds (Table 2 and Fig 2). C—H···π interactions exist between C15—H15A and Cg(1)i, the centroid of the benzene ring C13—C18 [symmetry code: (i) –X,1/2-Y,1/2+Z]. There are π-stacking interactions between the naphthylamide groups, with distances between ring centroids of 3.718 (2), 3.510 (2) and 3.546 (2) Å, for Cg(2)···Cg(3)ii, Cg(3)···Cg(2)iii and Cg(2)···Cg(4)ii, respectively [Cg(2) = C2—C6/C11, Cg(3) = C1—C2/N1/C10—C12, Cg(4)=C6—C11; symmetry codes: (ii) 1/2-X,Y,-1/2 + z; (iii) 1/2-X,Y,1/2 + z].