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The title compound, C19H12N2O4, was synthesized by dehydrative condensation of maleic anhydride and N-benzyl-4-amino­phthal­imide. In the structure, the male­imide ring is rotated by 43.8 (3)° with respect to the phthal­imide plane. The dihedral angle between the mean planes of the phthal­imide and benzyl groups is 91.0 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014181/lh6074sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014181/lh6074Isup2.hkl
Contains datablock I

CCDC reference: 217622

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.115
  • Data-to-parameter ratio = 11.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

N-Substituted maleimides are among such types of organic compounds with numerous applications in synthetic and polymer chemistry. A search of the literature revealed that some N-substituted maleimide have important biological properties, such as, antimicrobial activity (Zentz et al., 2002), antibacterial activity (Filho et al., 1994) and antitumor activity (Kratz et al., 1997). Some phthalimide derivatives had cytotoxicity (Hall et al., 1995) and anti-HIV activity (Van Derpoorten et al., 1997). It was assumed that compounds having both phthalimide and maleimide residues in the same molecule may possess some attractive biological activities. With this in mind, the synthesis and structure determination of the title compound, (I), was undertaken.

The phthalimide group is planar, the mean deviation from the least-squares plane being 0.010 (3) Å. This observation is in good agreement with our previous report in ethyl N-(2-butyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl) carbamate (Shi et al., 2003). The maleimide moiety is also planar, the mean deviation of the atoms from this plane is 0.008 (3) Å. The dihedral angle between the mean planes of the phthalimide plane and maleimide ring is 43.8 (3)°, which is somewhat different from the corresponding angles found in bis(4-maleimidophenyl)methane, viz. 52.1 (1)° (Usman et al., 2003) and N-(4-hydroxyphenyl)maleimide, viz. 52.8 (5)° (Rodriguez et al., 2002). The benzyl group and phthalimide group are folded towards each other, making an angle of 91.0 (2)°.

Experimental top

To a stirred solution of maleic anhydride (22 mmol) in 20 ml of acetone was added dropwise a solution of N-benzyl-4-aminophthalimide (20 mmol) in 30 ml of acetone. After an addition time of 1 h, the maleamic acid separated almost immediately at room temperature. After stirring for 3 h to insure complete reaction, 0.3 ml of triethylamine and 4 ml of acetic anhydride was added. The mixture was heated to 323 K and kept at this temperature for 1 h. Then, the mixture was diluted with four volumes of cold water, thereby precipitating (I) as fine white feathery needles. M.p. 426–428 K; IR (KBr): 3080 (C—H), 1730 (CO) cm−1; 1H NMR (CDCl3, p.p.m.): 4.86 (2H, s), 6.93 (2H, s), 7.26–7.43 (5H, m), 7.78 (1H, d), 7.92–7.95 (2H, m). Compound (I) (50 mg) was dissolved in chloroform (15 ml) and the solution was kept at room temperature for 3 d, yielding colorless single crystals.

Refinement top

All H atoms were placed in calculated positions with C—H distances of 0.93 (sp2) and 0.97 Å (sp3), and included in the refinement in riding-motion approximation, with Uiso = 1.2Ueq of the carrier atom.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal structure of (I), viewed along the a axis.
2-Benzyl-5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2,3-dihydro- 1H-isoindole-1,3-dione top
Crystal data top
C19H12N2O4Z = 2
Mr = 332.31F(000) = 344
Triclinic, P1Dx = 1.428 Mg m3
Dm = not mesaured Mg m3
Dm measured by none
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.061 (2) ÅCell parameters from 997 reflections
b = 11.803 (4) Åθ = 3.1–26.3°
c = 14.186 (5) ŵ = 0.10 mm1
α = 112.607 (6)°T = 293 K
β = 94.050 (6)°Plate, colorless
γ = 95.755 (6)°0.25 × 0.20 × 0.15 mm
V = 772.8 (5) Å3
Data collection top
Bruker SMART CCD
diffractometer
2700 independent reflections
Radiation source: fine-focus sealed tube2082 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ϕ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 56
Tmin = 0.976, Tmax = 0.985k = 1014
3218 measured reflectionsl = 1616
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0604P)2 + 0.1101P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.17 e Å3
2700 reflectionsΔρmin = 0.20 e Å3
226 parameters
Crystal data top
C19H12N2O4γ = 95.755 (6)°
Mr = 332.31V = 772.8 (5) Å3
Triclinic, P1Z = 2
a = 5.061 (2) ÅMo Kα radiation
b = 11.803 (4) ŵ = 0.10 mm1
c = 14.186 (5) ÅT = 293 K
α = 112.607 (6)°0.25 × 0.20 × 0.15 mm
β = 94.050 (6)°
Data collection top
Bruker SMART CCD
diffractometer
2700 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2082 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.985Rint = 0.014
3218 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.06Δρmax = 0.17 e Å3
2700 reflectionsΔρmin = 0.20 e Å3
226 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.2581 (3)0.95332 (12)0.03582 (12)0.0541 (4)
O20.1897 (4)0.53200 (13)0.07670 (12)0.0703 (5)
O30.4487 (3)0.56491 (13)0.30525 (11)0.0582 (4)
O41.1962 (3)0.85166 (14)0.39137 (12)0.0584 (4)
N10.2824 (3)0.74661 (13)0.00293 (12)0.0403 (4)
N20.8442 (3)0.69878 (14)0.36710 (12)0.0420 (4)
C10.1916 (4)0.84475 (18)0.01689 (15)0.0420 (5)
C20.0020 (4)0.7862 (2)0.11143 (16)0.0527 (5)
H20.09460.82880.14320.063*
C30.0225 (5)0.6654 (2)0.14331 (16)0.0569 (6)
H30.13130.60880.20120.068*
C40.1553 (4)0.63295 (18)0.07246 (15)0.0484 (5)
C50.4677 (4)0.76075 (16)0.08860 (13)0.0361 (4)
C60.6924 (4)0.85051 (17)0.11607 (14)0.0402 (4)
H60.71830.89920.07840.048*
C70.8772 (4)0.86784 (17)0.19883 (15)0.0417 (5)
H71.02800.92710.21710.050*
C80.8309 (3)0.79450 (16)0.25334 (13)0.0365 (4)
C90.9886 (4)0.79070 (17)0.34436 (15)0.0417 (4)
C100.6109 (4)0.64521 (16)0.30038 (14)0.0410 (5)
C110.6050 (4)0.70617 (15)0.22588 (13)0.0362 (4)
C120.4192 (4)0.68696 (16)0.14388 (14)0.0390 (4)
H120.26850.62770.12610.047*
C130.9164 (4)0.67065 (18)0.45678 (15)0.0467 (5)
H13A1.10270.70310.48270.056*
H13B0.89650.58150.43600.056*
C140.7450 (4)0.72543 (16)0.54179 (14)0.0398 (4)
C150.6449 (4)0.65706 (18)0.59523 (15)0.0493 (5)
H150.68360.57670.57870.059*
C160.4883 (5)0.7074 (2)0.67279 (17)0.0575 (6)
H160.42240.66090.70820.069*
C170.4292 (5)0.8259 (2)0.69785 (17)0.0571 (6)
H170.32240.85940.74970.069*
C180.5291 (5)0.89469 (19)0.64582 (17)0.0555 (6)
H180.49120.97520.66310.067*
C190.6849 (4)0.84494 (18)0.56838 (16)0.0491 (5)
H190.75060.89210.53340.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0522 (9)0.0411 (8)0.0706 (10)0.0046 (6)0.0018 (7)0.0259 (7)
O20.0978 (13)0.0408 (9)0.0602 (10)0.0156 (8)0.0105 (9)0.0086 (7)
O30.0688 (10)0.0499 (8)0.0587 (9)0.0105 (7)0.0060 (8)0.0315 (7)
O40.0487 (9)0.0658 (9)0.0620 (10)0.0065 (7)0.0096 (8)0.0328 (8)
N10.0458 (9)0.0388 (8)0.0371 (9)0.0079 (7)0.0026 (7)0.0156 (7)
N20.0480 (10)0.0419 (9)0.0388 (9)0.0056 (7)0.0007 (7)0.0196 (7)
C10.0394 (11)0.0477 (12)0.0465 (11)0.0083 (8)0.0080 (9)0.0259 (9)
C20.0520 (13)0.0617 (14)0.0506 (13)0.0093 (10)0.0004 (10)0.0295 (11)
C30.0639 (15)0.0604 (14)0.0404 (12)0.0070 (11)0.0061 (10)0.0158 (10)
C40.0585 (13)0.0421 (11)0.0396 (11)0.0106 (9)0.0038 (10)0.0101 (9)
C50.0396 (10)0.0365 (9)0.0329 (10)0.0109 (8)0.0060 (8)0.0127 (8)
C60.0415 (11)0.0421 (10)0.0437 (11)0.0089 (8)0.0100 (9)0.0224 (9)
C70.0376 (10)0.0433 (10)0.0468 (11)0.0035 (8)0.0075 (9)0.0207 (9)
C80.0357 (10)0.0363 (9)0.0379 (10)0.0094 (8)0.0070 (8)0.0137 (8)
C90.0416 (11)0.0405 (10)0.0435 (11)0.0078 (8)0.0055 (9)0.0165 (9)
C100.0509 (12)0.0335 (10)0.0383 (10)0.0058 (8)0.0042 (9)0.0141 (8)
C110.0413 (10)0.0317 (9)0.0357 (10)0.0089 (8)0.0073 (8)0.0119 (7)
C120.0416 (11)0.0335 (9)0.0403 (10)0.0038 (8)0.0045 (9)0.0131 (8)
C130.0544 (12)0.0462 (11)0.0449 (11)0.0112 (9)0.0012 (9)0.0241 (9)
C140.0421 (11)0.0402 (10)0.0354 (10)0.0019 (8)0.0068 (8)0.0159 (8)
C150.0628 (13)0.0425 (11)0.0454 (12)0.0060 (9)0.0026 (10)0.0223 (9)
C160.0711 (15)0.0607 (14)0.0498 (13)0.0044 (11)0.0100 (11)0.0326 (11)
C170.0626 (14)0.0598 (14)0.0479 (12)0.0082 (11)0.0102 (11)0.0195 (10)
C180.0658 (15)0.0418 (11)0.0575 (13)0.0099 (10)0.0094 (11)0.0169 (10)
C190.0571 (13)0.0419 (11)0.0515 (12)0.0025 (9)0.0066 (10)0.0229 (9)
Geometric parameters (Å, º) top
O1—C11.207 (2)C7—H70.9300
O2—C41.201 (2)C8—C111.390 (3)
O3—C101.216 (2)C8—C91.487 (3)
O4—C91.203 (2)C10—C111.490 (2)
N1—C11.404 (2)C11—C121.374 (3)
N1—C41.409 (2)C12—H120.9300
N1—C51.427 (2)C13—C141.512 (3)
N2—C101.386 (3)C13—H13A0.9700
N2—C91.400 (2)C13—H13B0.9700
N2—C131.465 (2)C14—C191.385 (3)
C1—C21.484 (3)C14—C151.387 (3)
C2—C31.310 (3)C15—C161.381 (3)
C2—H20.9300C15—H150.9300
C3—C41.484 (3)C16—C171.374 (3)
C3—H30.9300C16—H160.9300
C5—C121.394 (2)C17—C181.375 (3)
C5—C61.395 (3)C17—H170.9300
C6—C71.385 (3)C18—C191.376 (3)
C6—H60.9300C18—H180.9300
C7—C81.379 (2)C19—H190.9300
C1—N1—C4109.52 (16)O3—C10—N2124.77 (17)
C1—N1—C5124.88 (15)O3—C10—C11128.95 (19)
C4—N1—C5125.56 (15)N2—C10—C11106.27 (15)
C10—N2—C9112.12 (15)C12—C11—C8122.29 (16)
C10—N2—C13123.58 (16)C12—C11—C10130.08 (17)
C9—N2—C13124.05 (17)C8—C11—C10107.62 (16)
O1—C1—N1125.19 (19)C11—C12—C5116.69 (17)
O1—C1—C2128.94 (18)C11—C12—H12121.7
N1—C1—C2105.85 (16)C5—C12—H12121.7
C3—C2—C1109.50 (19)N2—C13—C14112.12 (15)
C3—C2—H2125.2N2—C13—H13A109.2
C1—C2—H2125.2C14—C13—H13A109.2
C2—C3—C4109.33 (19)N2—C13—H13B109.2
C2—C3—H3125.3C14—C13—H13B109.2
C4—C3—H3125.3H13A—C13—H13B107.9
O2—C4—N1125.68 (19)C19—C14—C15118.46 (18)
O2—C4—C3128.52 (19)C19—C14—C13120.88 (17)
N1—C4—C3105.80 (17)C15—C14—C13120.66 (16)
C12—C5—C6121.51 (17)C16—C15—C14120.48 (18)
C12—C5—N1119.82 (16)C16—C15—H15119.8
C6—C5—N1118.66 (16)C14—C15—H15119.8
C7—C6—C5120.71 (17)C17—C16—C15120.34 (19)
C7—C6—H6119.6C17—C16—H16119.8
C5—C6—H6119.6C15—C16—H16119.8
C8—C7—C6117.98 (17)C16—C17—C18119.6 (2)
C8—C7—H7121.0C16—C17—H17120.2
C6—C7—H7121.0C18—C17—H17120.2
C7—C8—C11120.81 (17)C19—C18—C17120.32 (19)
C7—C8—C9130.76 (17)C19—C18—H18119.8
C11—C8—C9108.42 (16)C17—C18—H18119.8
O4—C9—N2125.07 (18)C18—C19—C14120.81 (19)
O4—C9—C8129.39 (18)C18—C19—H19119.6
N2—C9—C8105.54 (16)C14—C19—H19119.6
C4—N1—C1—O1177.81 (18)C11—C8—C9—N20.35 (19)
C5—N1—C1—O10.1 (3)C9—N2—C10—O3178.54 (18)
C4—N1—C1—C20.6 (2)C13—N2—C10—O34.1 (3)
C5—N1—C1—C2178.44 (16)C9—N2—C10—C111.1 (2)
O1—C1—C2—C3178.1 (2)C13—N2—C10—C11175.54 (15)
N1—C1—C2—C30.2 (2)C7—C8—C11—C120.4 (3)
C1—C2—C3—C40.2 (2)C9—C8—C11—C12179.78 (15)
C1—N1—C4—O2179.8 (2)C7—C8—C11—C10178.84 (15)
C5—N1—C4—O22.0 (3)C9—C8—C11—C101.02 (19)
C1—N1—C4—C30.7 (2)O3—C10—C11—C120.8 (3)
C5—N1—C4—C3178.54 (17)N2—C10—C11—C12179.56 (17)
C2—C3—C4—O2180.0 (2)O3—C10—C11—C8178.33 (19)
C2—C3—C4—N10.5 (2)N2—C10—C11—C81.33 (19)
C1—N1—C5—C12135.55 (18)C8—C11—C12—C50.1 (2)
C4—N1—C5—C1242.0 (2)C10—C11—C12—C5179.06 (16)
C1—N1—C5—C643.3 (2)C6—C5—C12—C110.7 (2)
C4—N1—C5—C6139.11 (19)N1—C5—C12—C11179.56 (15)
C12—C5—C6—C70.9 (3)C10—N2—C13—C1471.9 (2)
N1—C5—C6—C7179.81 (15)C9—N2—C13—C14101.8 (2)
C5—C6—C7—C80.5 (3)N2—C13—C14—C1943.1 (3)
C6—C7—C8—C110.1 (3)N2—C13—C14—C15137.13 (18)
C6—C7—C8—C9179.96 (17)C19—C14—C15—C160.2 (3)
C10—N2—C9—O4179.28 (19)C13—C14—C15—C16180.0 (2)
C13—N2—C9—O44.9 (3)C14—C15—C16—C170.1 (3)
C10—N2—C9—C80.53 (19)C15—C16—C17—C180.6 (3)
C13—N2—C9—C8174.90 (15)C16—C17—C18—C190.7 (3)
C7—C8—C9—O40.3 (3)C17—C18—C19—C140.3 (3)
C11—C8—C9—O4179.9 (2)C15—C14—C19—C180.1 (3)
C7—C8—C9—N2179.50 (17)C13—C14—C19—C18179.9 (2)

Experimental details

Crystal data
Chemical formulaC19H12N2O4
Mr332.31
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.061 (2), 11.803 (4), 14.186 (5)
α, β, γ (°)112.607 (6), 94.050 (6), 95.755 (6)
V3)772.8 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.976, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
3218, 2700, 2082
Rint0.014
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.115, 1.06
No. of reflections2700
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.20

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C11.207 (2)N1—C51.427 (2)
O2—C41.201 (2)N2—C131.465 (2)
O3—C101.216 (2)C2—C31.310 (3)
O4—C91.203 (2)
C1—N1—C4109.52 (16)C2—C3—C4109.33 (19)
C10—N2—C9112.12 (15)C6—C5—N1118.66 (16)
C10—N2—C13123.58 (16)N2—C13—C14112.12 (15)
C4—N1—C5—C1242.0 (2)N2—C13—C14—C1943.1 (3)
C1—N1—C5—C643.3 (2)N2—C13—C14—C15137.13 (18)
 

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