2-Benzyl­isoindoline-1,3-dione: a monoclinic polymorph

Jiang, Z.; Wang, J.-D.; Chen, N.-S.; Huang, J.-L.

doi:10.1107/S1600536807065336

organic compounds

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Volume 64| Part 1| January 2008| Page o324

https://doi.org/10.1107/S1600536807065336

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2-Benzylisoindoline-1,3-dione: a monoclinic polymorph

Zhou Jiang,^a Jun-Dong Wang,^a ^* Nai-Sheng Chen ^a and Jin-Ling Huang ^a

^aInstitute of Research on Functional Materials, Department of Chemistry, University of FuZhou, Fuzhou 350002, People's Republic of China
^*Correspondence e-mail: wangjd@fzu.edu.cn

(Received 29 November 2007; accepted 4 December 2007; online 21 December 2007)

In the molecule of the title compound, C₁₅H₁₁NO₂, the dihedral angle between the ring systems is 81.3 (2)°. In the crystal structure, molecules are held together via C—H⋯O interactions.

Related literature

For the crystal structure of the triclinic form, see: Warzecha, Lex & Griesbeck (2006 ). For related literature, see: Warzecha, Görner & Griesbeck (2006 ); Orzeszko et al. (2000 ).

Experimental

Crystal data

C₁₅H₁₁NO₂
M_r = 237.25
Monoclinic, P 2₁ /n
a = 8.8324 (6) Å
b = 5.3656 (4) Å
c = 25.1926 (18) Å
β = 98.851 (3)°
V = 1179.69 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.8 × 0.2 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: none
3668 measured reflections
2083 independent reflections
1439 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.097
wR(F²) = 0.192
S = 1.26
2083 reflections
208 parameters
All H-atom parameters refined
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H7⋯O1ⁱ	1.03 (6)	2.43 (6)	3.425 (6)	161 (5)
C3—H1⋯O2ⁱⁱ	0.98 (5)	2.54 (5)	3.363 (7)	142 (4)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku, 2006 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807065336/tk2231sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065336/tk2231Isup2.hkl

checkCIF report

Comment top

The title compound, N-Benzylphthalimide (2-benzylisoindoline-1,3-dione) (I), plays an important role in photoinduced electron transfer (PET) reactions (Warzecha, Görner & Griesbeck, 2006). Warzecha, Lex & Griesbeck (2006) also reported the crystal structure of the triclinic form of (I). Herein, the crystal structure of a monoclinic form is described.

The molecular structure of (I), Fig. 1, shows two planar subunits, i.e. a phthalimide moiety and a phenyl ring, being linked by a methylene-C9 atom with a N1—C9—C10 bond angle of 114.2 (5)°. The dihedral angle formed between the least-squares planes through each of the subunits is 81.3 (2)°. The C8—N1—C9—C10 and C7—N1—C9—C10 torsion angles of 91.3 (6)Å and -88.0 (6)°, respectively, highlight the orthogonal relationship within the molecule.

The crystal packing is stabilized by C—H···O interactions (Table 1).

Related literature top

For related literature, see: Warzecha, Görner & Griesbeck (2006); Warzecha, Lex & Griesbeck (2006>); Orzeszko et al. (2000).

Experimental top

Compound (I) was purified by silica-gel column chromatography with alcohol-hexane (v/v = 3/7) as eluent. Single crystals were obtained by slow evaporation of the eluting solution at room temperature.

Structure description top

The crystal packing is stabilized by C—H···O interactions (Table 1).

For related literature, see: Warzecha, Görner & Griesbeck (2006); Warzecha, Lex & Griesbeck (2006>); Orzeszko et al. (2000).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 35% probability level.

2-Benzylisoindoline-1,3-dione top

Crystal data top

C₁₅H₁₁NO₂	F(000) = 496
M_r = 237.25	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 3962 reflections
a = 8.8324 (6) Å	θ = 1.2–25.0°
b = 5.3656 (4) Å	µ = 0.09 mm⁻¹
c = 25.1926 (18) Å	T = 298 K
β = 98.851 (3)°	Needle, colorless
V = 1179.69 (15) Å³	0.8 × 0.2 × 0.1 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1439 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode generator	R_int = 0.048
Graphite Monochromator monochromator	θ_max = 25.0°, θ_min = 1.6°
ω scans	h = −10→9
3668 measured reflections	k = −6→6
2083 independent reflections	l = −29→13

Refinement top

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)] = 0.097	All H-atom parameters refined
wR(F²) = 0.192	w = 1/[σ²(F_o²) + (0.0216P)² + 2.0256P] where P = (F_o² + 2F_c²)/3
S = 1.26	(Δ/σ)_max < 0.001
2083 reflections	Δρ_max = 0.24 e Å⁻³
208 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Crystal data top

C₁₅H₁₁NO₂	V = 1179.69 (15) Å³
M_r = 237.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.8324 (6) Å	µ = 0.09 mm⁻¹
b = 5.3656 (4) Å	T = 298 K
c = 25.1926 (18) Å	0.8 × 0.2 × 0.1 mm
β = 98.851 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1439 reflections with I > 2σ(I)
3668 measured reflections	R_int = 0.048
2083 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.097	0 restraints
wR(F²) = 0.192	All H-atom parameters refined
S = 1.26	Δρ_max = 0.24 e Å⁻³
2083 reflections	Δρ_min = −0.19 e Å⁻³
208 parameters

Special details top

Experimental. collimator diameter: 0.800000 mm

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

	x	y	z	U_iso*/U_eq
O2	0.5810 (4)	0.7318 (7)	0.08609 (13)	0.0656 (10)
N1	0.7327 (4)	1.0824 (8)	0.09212 (14)	0.0520 (11)
O1	0.8908 (4)	1.4018 (7)	0.07261 (13)	0.0679 (11)
H1	0.579 (6)	0.595 (10)	−0.030 (2)	0.081*
H5	0.631 (6)	1.076 (10)	0.1573 (18)	0.070 (15)*
H10	1.040 (6)	1.130 (11)	0.309 (2)	0.085*
H4	0.895 (6)	1.300 (11)	−0.042 (2)	0.085*
H6	0.717 (7)	1.326 (13)	0.149 (2)	0.11 (2)*
H11	0.834 (6)	1.292 (12)	0.244 (2)	0.10 (2)*
H9	1.167 (6)	0.743 (11)	0.291 (2)	0.090 (18)*
H2	0.666 (6)	0.677 (11)	−0.112 (2)	0.082 (17)*
H3	0.815 (6)	1.037 (10)	−0.120 (2)	0.081 (16)*
H8	1.099 (7)	0.588 (12)	0.204 (2)	0.10 (2)*
H7	0.905 (7)	0.729 (12)	0.140 (2)	0.115*
C1	0.7860 (5)	1.0946 (9)	0.00582 (17)	0.0476 (12)
C2	0.6932 (5)	0.8927 (9)	0.00966 (17)	0.0483 (12)
C3	0.6470 (6)	0.7357 (11)	−0.0330 (2)	0.0599 (14)
C4	0.6984 (7)	0.7930 (12)	−0.0809 (2)	0.0670 (15)
C5	0.7910 (6)	0.9958 (12)	−0.0849 (2)	0.0676 (16)
C6	0.8377 (6)	1.1518 (11)	−0.0419 (2)	0.0600 (14)
C7	0.8157 (5)	1.2218 (9)	0.05865 (18)	0.0495 (12)
C8	0.6581 (5)	0.8804 (10)	0.06590 (18)	0.0509 (12)
C9	0.7296 (7)	1.1484 (13)	0.1487 (2)	0.0620 (14)
C10	0.8568 (5)	1.0365 (9)	0.18740 (17)	0.0495 (12)
C11	0.8977 (7)	1.1438 (12)	0.2375 (2)	0.0652 (15)
C12	1.0108 (8)	1.0414 (13)	0.2747 (2)	0.0787 (19)
C13	1.0886 (7)	0.8336 (13)	0.2625 (2)	0.0744 (17)
C14	1.0491 (7)	0.7241 (13)	0.2137 (2)	0.0711 (16)
C15	0.9351 (6)	0.8245 (10)	0.1757 (2)	0.0581 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.069 (2)	0.063 (2)	0.066 (2)	−0.012 (2)	0.0146 (17)	0.0088 (19)
N1	0.058 (2)	0.052 (3)	0.046 (2)	0.001 (2)	0.0091 (18)	−0.002 (2)
O1	0.073 (2)	0.054 (2)	0.077 (2)	−0.012 (2)	0.0135 (18)	−0.015 (2)
C1	0.045 (2)	0.041 (3)	0.056 (3)	0.003 (2)	0.007 (2)	0.004 (2)
C2	0.048 (2)	0.049 (3)	0.047 (2)	0.008 (2)	0.0045 (19)	0.005 (2)
C3	0.058 (3)	0.064 (4)	0.056 (3)	−0.003 (3)	0.004 (2)	−0.002 (3)
C4	0.075 (4)	0.068 (4)	0.057 (3)	0.004 (3)	0.008 (3)	−0.008 (3)
C5	0.070 (3)	0.083 (4)	0.052 (3)	0.013 (3)	0.016 (3)	0.008 (3)
C6	0.058 (3)	0.064 (4)	0.060 (3)	0.000 (3)	0.017 (2)	0.006 (3)
C7	0.048 (3)	0.041 (3)	0.059 (3)	0.005 (2)	0.004 (2)	−0.004 (2)
C8	0.049 (3)	0.051 (3)	0.053 (3)	0.004 (3)	0.005 (2)	0.004 (3)
C9	0.069 (3)	0.064 (4)	0.055 (3)	0.010 (3)	0.017 (2)	−0.005 (3)
C10	0.060 (3)	0.047 (3)	0.045 (2)	−0.007 (3)	0.017 (2)	0.001 (2)
C11	0.080 (4)	0.065 (4)	0.052 (3)	−0.005 (3)	0.014 (3)	−0.008 (3)
C12	0.101 (5)	0.088 (5)	0.044 (3)	−0.017 (4)	0.002 (3)	−0.005 (3)
C13	0.074 (4)	0.080 (5)	0.067 (4)	−0.002 (4)	0.004 (3)	0.013 (4)
C14	0.072 (4)	0.067 (4)	0.074 (4)	0.007 (3)	0.011 (3)	0.003 (3)
C15	0.064 (3)	0.055 (3)	0.056 (3)	−0.001 (3)	0.012 (2)	−0.001 (3)

Geometric parameters (Å, º) top

O2—C8	1.210 (5)	C6—H4	0.94 (6)
N1—C8	1.383 (6)	C9—C10	1.496 (7)
N1—C7	1.413 (6)	C9—H5	1.01 (5)
N1—C9	1.473 (6)	C9—H6	0.96 (7)
O1—C7	1.193 (5)	C10—C11	1.383 (6)
C1—C2	1.371 (6)	C10—C15	1.386 (7)
C1—C6	1.384 (6)	C11—C12	1.376 (8)
C1—C7	1.483 (6)	C11—H11	1.00 (6)
C2—C3	1.377 (7)	C12—C13	1.370 (8)
C2—C8	1.498 (6)	C12—H10	0.99 (5)
C3—C4	1.388 (7)	C13—C14	1.359 (8)
C3—H1	0.98 (5)	C13—H9	1.04 (6)
C4—C5	1.374 (8)	C14—C15	1.385 (7)
C4—H2	1.00 (5)	C14—H8	0.91 (6)
C5—C6	1.382 (7)	C15—H7	1.03 (6)
C5—H3	0.97 (5)

C8—N1—C7	112.5 (4)	N1—C8—C2	105.3 (4)
C8—N1—C9	124.9 (4)	N1—C9—C10	114.2 (4)
C7—N1—C9	122.6 (4)	N1—C9—H5	105 (3)
C2—C1—C6	121.1 (4)	C10—C9—H5	107 (3)
C2—C1—C7	109.0 (4)	N1—C9—H6	105 (4)
C6—C1—C7	129.8 (5)	C10—C9—H6	118 (4)
C1—C2—C3	122.5 (4)	H5—C9—H6	106 (5)
C1—C2—C8	108.3 (4)	C11—C10—C15	117.8 (5)
C3—C2—C8	129.2 (5)	C11—C10—C9	119.5 (5)
C2—C3—C4	116.5 (5)	C15—C10—C9	122.7 (4)
C2—C3—H1	122 (3)	C12—C11—C10	121.1 (6)
C4—C3—H1	122 (3)	C12—C11—H11	124 (3)
C5—C4—C3	121.1 (5)	C10—C11—H11	114 (3)
C5—C4—H2	123 (3)	C13—C12—C11	120.5 (6)
C3—C4—H2	116 (3)	C13—C12—H10	121 (3)
C4—C5—C6	122.1 (5)	C11—C12—H10	118 (3)
C4—C5—H3	117 (3)	C14—C13—C12	119.2 (6)
C6—C5—H3	120 (3)	C14—C13—H9	118 (3)
C5—C6—C1	116.7 (5)	C12—C13—H9	122 (3)
C5—C6—H4	127 (3)	C13—C14—C15	121.0 (6)
C1—C6—H4	116 (3)	C13—C14—H8	122 (4)
O1—C7—N1	124.6 (4)	C15—C14—H8	117 (4)
O1—C7—C1	130.6 (5)	C14—C15—C10	120.4 (5)
N1—C7—C1	104.8 (4)	C14—C15—H7	118 (3)
O2—C8—N1	125.0 (4)	C10—C15—H7	122 (3)
O2—C8—C2	129.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H7···O1ⁱ	1.03 (6)	2.43 (6)	3.425 (6)	161 (5)
C3—H1···O2ⁱⁱ	0.98 (5)	2.54 (5)	3.363 (7)	142 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO₂
M_r	237.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.8324 (6), 5.3656 (4), 25.1926 (18)
β (°)	98.851 (3)
V (Å³)	1179.69 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.8 × 0.2 × 0.1

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3668, 2083, 1439
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.097, 0.192, 1.26
No. of reflections	2083
No. of parameters	208
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: RAPID-AUTO (Rigaku, 2006), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H7···O1ⁱ	1.03 (6)	2.43 (6)	3.425 (6)	161 (5)
C3—H1···O2ⁱⁱ	0.98 (5)	2.54 (5)	3.363 (7)	142 (4)

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

Acknowledgements

This work was supported by the Young Scientist Innovation Foundation of Fujian Province of China (No. 2006F3071).

References

McArdle, P. (1995). J. Appl. Cryst. 28, 65. CrossRef IUCr Journals Google Scholar
Orzeszko, A., Kaminska, B., Orzesko, G. & Starosciak, J. (2000). Il Farmaco, 55, 619-623. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2006). RAPID-AUTO. Version 3.0. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Warzecha, K.-D., Görner, H. & Griesbeck, A. G. (2006). J. Phys. Chem. A, 110, 3356–3363. Web of Science CrossRef PubMed CAS Google Scholar
Warzecha, K.-D., Lex, J. & Griesbeck, A. G. (2006). Acta Cryst. E62, o2367–o2368. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar