N-(Imidazol-1-ylmeth­yl)phthalimide

Wang, S.-Q.; Jian, F.-F.; Liu, H.-Q.

doi:10.1107/S1600536808025154

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1750

doi:10.1107/S1600536808025154

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N-(Imidazol-1-ylmethyl)phthalimide

Su-Qing Wang,^a Fang-Fang Jian ^a ^* and Huan-Qiang Liu ^b

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 24 July 2008; accepted 5 August 2008; online 13 August 2008)

The title compound [systematic name: 2-(imidazol-1-ylmethyl)isoindole-1,3-dione], C₁₂H₉N₃O₂, was prepared by reaction of N-(bromomethyl)phthalimide and imidazole in chloroform solution. The crystal structure is stabilized by weak intermolecular C—H⋯π interactions and intermolecular π–π interactions with centroid–centroid distances in the range 3.6469 (8)–3.8831 (9) Å.

Related literature

For related literature, see: Brooks & Davidson (1960 ); Zhao et al. (2000 ); Barszcz et al. (2004 ); Jian et al. (2004 ).

Experimental

Crystal data

C₁₂H₉N₃O₂
M_r = 227.22
Monoclinic, P 2₁ /c
a = 7.9905 (6) Å
b = 19.8096 (15) Å
c = 6.9229 (5) Å
β = 105.5540 (10)°
V = 1055.69 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.2 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
6792 measured reflections
2556 independent reflections
1868 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 1.03
2556 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Selected interatomic distances (Å)

Cg1, Cg2 and Cg3 are the centroids of the N1/N3/C1–C3, N3/C5/C6/C11/C12 and C6–C11 rings, respectively.

Cg1⋯Cg1ⁱ	3.8831 (9)
Cg2⋯Cg3ⁱⁱ	3.6985 (8)
Cg2⋯Cg3ⁱⁱⁱ	3.6469 (8)
Cg3⋯Cg3ⁱⁱ	3.7214 (8)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N3/C1–C3 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg1^iv	0.93	2.94	3.6105 (15)	130
Symmetry code: (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025154/at2605sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025154/at2605Isup2.hkl

checkCIF report

Comment top

The imidazole and its derivatives are of considerable interest as the ligands in many biological systems in which they provide the potential binding site for metal ions (Brooks et al., 1960). In our search for new ligands of this type, we have synthesized the title compound (I), and describe its structure here.

In the crystal structure of (I) (Fig. 1), the C═O bond lengths are 1.2030 (15) and 1.2026 (15) Å. The C—N bond lengths are in agreement with those observed before (Zhao et al., 2000). The dihedral angles formed by the N1/N2/C1-C3 and N3/C5/C6/C11/C12 rings, with the C6-C12 ring, are 70.95 (7) ang 0.44 (7)°, respectively.

The crystal structure is stabilized by weak intermolecular C—H···π interactions and intermolecular π–π interactions with centroid-to-centroid distances of 3.6469 (8)–3.8831 (9) Å (Table 1). The crystal packing of the title compound is shown in Fig. 2, viewed down the a axis.

Related literature top

For related literature, see: Brooks & Davidson (1960); Zhao et al. (2000); Barszcz et al. (2004); Jian et al. (2004). Cg1, Cg2 and Cg3 are the centroids of the N1/N3/C1–C3, N3/C5/C6/C11/C12 and C6–C11 rings, respectively.

Experimental top

N-bromomethyl phthalic imidine 7.2 g (0.03 mol) and imidazole 2.04 g (0.03 mol) were dissolved in 20 ml chloroform. The solution was cooled to 283 K. Then, 3 g (0.03 mol) triethylamine was added dropwise via cannula into the well stirred solution.The reaction mixture was stirred at 283 K for 6 h. Then the solution was continued to stir at room temperature about 17 h. 20 ml water was added into the solution, the organic phase was seperated and dryed with anhydrous potassium carbonate. The colourless organic phase was evaporated. The title compound is afforded in 65% yield. The colourless crystals of suitable for X-ray determination were obtained from anhydrous ethanol at room temperature after two days.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I), viewed down the a axis.

2-(Imidazol-1-ylmethyl)isoindole-1,3-dione top

Crystal data top

C₁₂H₉N₃O₂	F(000) = 472
M_r = 227.22	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2256 reflections
a = 7.9905 (6) Å	θ = 2.1–28.3°
b = 19.8096 (15) Å	µ = 0.10 mm⁻¹
c = 6.9229 (5) Å	T = 273 K
β = 105.554 (1)°	Bar, colourless
V = 1055.69 (14) Å³	0.2 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1868 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 28.3°, θ_min = 2.1°
ϕ and ω scans	h = −7→10
6792 measured reflections	k = −25→26
2556 independent reflections	l = −8→9

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0428P)² + 0.1392P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2556 reflections	Δρ_max = 0.24 e Å⁻³
155 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), 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

C₁₂H₉N₃O₂	V = 1055.69 (14) Å³
M_r = 227.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9905 (6) Å	µ = 0.10 mm⁻¹
b = 19.8096 (15) Å	T = 273 K
c = 6.9229 (5) Å	0.2 × 0.15 × 0.15 mm
β = 105.554 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1868 reflections with I > 2σ(I)
6792 measured reflections	R_int = 0.027
2556 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2556 reflections	Δρ_min = −0.15 e Å⁻³
155 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

	x	y	z	U_iso*/U_eq
O1	0.38144 (13)	0.59386 (5)	0.45690 (16)	0.0582 (3)
O2	0.88708 (13)	0.71264 (5)	0.64832 (19)	0.0713 (3)
N1	0.79858 (19)	0.51519 (6)	0.1175 (2)	0.0656 (4)
N2	0.80767 (14)	0.55831 (5)	0.41391 (16)	0.0424 (3)
N3	0.65627 (13)	0.63862 (5)	0.56497 (15)	0.0407 (3)
C1	0.7178 (2)	0.52112 (7)	0.2578 (2)	0.0535 (4)
H1B	0.6103	0.5018	0.2505	0.064*
C2	0.9506 (2)	0.55038 (7)	0.1900 (3)	0.0604 (4)
H2A	1.0367	0.5550	0.1234	0.073*
C3	0.95804 (18)	0.57721 (7)	0.3700 (2)	0.0518 (4)
H3A	1.0472	0.6033	0.4488	0.062*
C4	0.75385 (19)	0.57605 (6)	0.5912 (2)	0.0471 (3)
H4A	0.8558	0.5806	0.7042	0.057*
H4B	0.6827	0.5400	0.6216	0.057*
C5	0.47554 (17)	0.64220 (6)	0.49665 (18)	0.0402 (3)
C6	0.43317 (15)	0.71539 (6)	0.48572 (17)	0.0382 (3)
C7	0.27516 (18)	0.74781 (7)	0.4294 (2)	0.0510 (3)
H7A	0.1717	0.7237	0.3900	0.061*
C8	0.2764 (2)	0.81774 (8)	0.4338 (2)	0.0582 (4)
H8A	0.1715	0.8410	0.3980	0.070*
C9	0.4295 (2)	0.85355 (7)	0.4899 (2)	0.0540 (4)
H9A	0.4259	0.9005	0.4911	0.065*
C10	0.58863 (18)	0.82107 (7)	0.54462 (18)	0.0476 (3)
H10A	0.6922	0.8452	0.5817	0.057*
C11	0.58717 (16)	0.75136 (6)	0.54189 (17)	0.0387 (3)
C12	0.73314 (17)	0.70263 (6)	0.59332 (19)	0.0441 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0538 (6)	0.0424 (6)	0.0806 (8)	−0.0112 (4)	0.0217 (5)	−0.0014 (5)
O2	0.0410 (6)	0.0627 (7)	0.1006 (9)	−0.0031 (5)	0.0027 (6)	−0.0102 (6)
N1	0.0894 (10)	0.0504 (7)	0.0696 (9)	−0.0025 (7)	0.0429 (8)	−0.0105 (6)
N2	0.0453 (6)	0.0332 (5)	0.0525 (6)	0.0058 (4)	0.0200 (5)	0.0031 (5)
N3	0.0417 (6)	0.0354 (6)	0.0464 (6)	0.0046 (4)	0.0141 (5)	−0.0016 (4)
C1	0.0633 (9)	0.0393 (7)	0.0639 (9)	−0.0074 (6)	0.0273 (7)	−0.0080 (6)
C2	0.0676 (10)	0.0490 (8)	0.0787 (11)	0.0133 (7)	0.0439 (9)	0.0093 (8)
C3	0.0412 (8)	0.0447 (7)	0.0723 (10)	0.0066 (6)	0.0200 (7)	0.0079 (7)
C4	0.0543 (8)	0.0416 (7)	0.0480 (7)	0.0114 (6)	0.0184 (6)	0.0063 (6)
C5	0.0440 (7)	0.0390 (7)	0.0411 (7)	−0.0014 (5)	0.0173 (5)	0.0002 (5)
C6	0.0425 (7)	0.0377 (6)	0.0353 (6)	0.0014 (5)	0.0122 (5)	−0.0005 (5)
C7	0.0437 (8)	0.0503 (8)	0.0565 (8)	0.0053 (6)	0.0090 (6)	−0.0003 (6)
C8	0.0590 (9)	0.0540 (9)	0.0558 (9)	0.0200 (7)	0.0054 (7)	0.0026 (7)
C9	0.0767 (11)	0.0362 (7)	0.0453 (7)	0.0095 (7)	0.0095 (7)	0.0013 (6)
C10	0.0610 (9)	0.0378 (7)	0.0421 (7)	−0.0048 (6)	0.0109 (6)	−0.0034 (5)
C11	0.0448 (7)	0.0378 (7)	0.0339 (6)	0.0002 (5)	0.0111 (5)	−0.0029 (5)
C12	0.0428 (7)	0.0439 (7)	0.0444 (7)	−0.0018 (6)	0.0095 (6)	−0.0055 (5)

Geometric parameters (Å, º) top

O1—C5	1.2030 (15)	C4—H4A	0.9700
O2—C12	1.2026 (15)	C4—H4B	0.9700
N1—C1	1.3075 (18)	C5—C6	1.4861 (17)
N1—C2	1.373 (2)	C6—C7	1.3764 (18)
N2—C1	1.3455 (17)	C6—C11	1.3843 (17)
N2—C3	1.3683 (16)	C7—C8	1.386 (2)
N2—C4	1.4487 (16)	C7—H7A	0.9300
N3—C5	1.3957 (17)	C8—C9	1.377 (2)
N3—C12	1.3996 (16)	C8—H8A	0.9300
N3—C4	1.4496 (15)	C9—C10	1.3845 (19)
C1—H1B	0.9300	C9—H9A	0.9300
C2—C3	1.341 (2)	C10—C11	1.3810 (18)
C2—H2A	0.9300	C10—H10A	0.9300
C3—H3A	0.9300	C11—C12	1.4820 (18)

Cg1···Cg1ⁱ	3.8831 (9)	Cg3···Cg2ⁱⁱⁱ	3.6985 (8)
Cg2···Cg3ⁱⁱ	3.6985 (8)	Cg3···Cg3ⁱⁱ	3.7214 (8)
Cg2···Cg3ⁱⁱⁱ	3.6469 (8)	Cg3···Cg3ⁱⁱⁱ	3.7214 (8)
Cg3···Cg2ⁱⁱ	3.6469 (8)

C1—N1—C2	104.28 (13)	O1—C5—C6	130.18 (13)
C1—N2—C3	106.40 (12)	N3—C5—C6	105.53 (10)
C1—N2—C4	126.73 (12)	C7—C6—C11	121.21 (12)
C3—N2—C4	126.86 (12)	C7—C6—C5	130.44 (12)
C5—N3—C12	112.14 (10)	C11—C6—C5	108.34 (11)
C5—N3—C4	123.97 (11)	C6—C7—C8	117.36 (13)
C12—N3—C4	123.78 (11)	C6—C7—H7A	121.3
N1—C1—N2	112.51 (13)	C8—C7—H7A	121.3
N1—C1—H1B	123.7	C9—C8—C7	121.47 (13)
N2—C1—H1B	123.7	C9—C8—H8A	119.3
C3—C2—N1	110.84 (13)	C7—C8—H8A	119.3
C3—C2—H2A	124.6	C8—C9—C10	121.27 (13)
N1—C2—H2A	124.6	C8—C9—H9A	119.4
C2—C3—N2	105.96 (13)	C10—C9—H9A	119.4
C2—C3—H3A	127.0	C11—C10—C9	117.21 (13)
N2—C3—H3A	127.0	C11—C10—H10A	121.4
N2—C4—N3	111.91 (10)	C9—C10—H10A	121.4
N2—C4—H4A	109.2	C10—C11—C6	121.47 (12)
N3—C4—H4A	109.2	C10—C11—C12	130.15 (12)
N2—C4—H4B	109.2	C6—C11—C12	108.38 (11)
N3—C4—H4B	109.2	O2—C12—N3	124.54 (12)
H4A—C4—H4B	107.9	O2—C12—C11	129.87 (13)
O1—C5—N3	124.30 (12)	N3—C12—C11	105.59 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cg1^iv	0.93	2.94	3.6105 (15)	130

Symmetry code: (iv) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₃O₂
M_r	227.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	7.9905 (6), 19.8096 (15), 6.9229 (5)
β (°)	105.554 (1)
V (Å³)	1055.69 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.2 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6792, 2556, 1868
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.03
No. of reflections	2556
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.15

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top

Cg1···Cg1ⁱ	3.8831 (9)	Cg3···Cg2ⁱⁱⁱ	3.6985 (8)
Cg2···Cg3ⁱⁱ	3.6985 (8)	Cg3···Cg3ⁱⁱ	3.7214 (8)
Cg2···Cg3ⁱⁱⁱ	3.6469 (8)	Cg3···Cg3ⁱⁱⁱ	3.7214 (8)
Cg3···Cg2ⁱⁱ	3.6469 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cg1^iv	0.93	2.94	3.6105 (15)	130

Symmetry code: (iv) −x+1, y−1/2, −z+1/2.

References

Barszcz, B., Glowiak, T., Jezierska, J. & Tomkiewicz, A. (2004). Polyhedron, 23, 1309–1316. Web of Science CSD CrossRef CAS Google Scholar
Brooks, P. & Davidson, N. (1960). J. Am. Chem. Soc. 82, 2118–2123. CrossRef CAS Web of Science Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jian, F.-F., Xiao, H.-L., Qin, Y.-Q. & Xu, L.-Z. (2004). Acta Cryst. C60, o492–o493. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, P. S., Jian, F. F., Lu, L. D., Yang, X. J. & Wang, X. (2000). Chinese J. Inorg. Chem. 16, 964–968. CAS Google Scholar

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doi:10.1107/S1600536808025154

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