(Z)-3-Acetonyl­idene-2,3-di­hydro-1H-isoindolin-1-one

The asymmetric unit of the title compound, C₁₁H₉NO₂, contains two mol­ecules which are related by a pseudo-inversion centre and form an N—H...O hydrogen-bonded dimer. The least-squares planes through the non-H atoms of the mol­ecules illustrate the overall molecular planarity. The mol­ecules assume Z configurations about the exocyclic C=C bond. In the crystal, intermolecular hydrogen bonds link the mol­ecules into infinite chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.121
• Data-to-parameter ratio = 19.1

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry

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S1. Comment

The isoindolinone skeleton is present in a number of natural products (Tamaoki et al., 1986; Valencia et al., 1985). Many isoindolinone derivatives exhibit biological activity as potential antiviral, antileukemic, anti-inflammatory, antipsychotic and antiulcer agents (Zhuang et al., 1998; Taylor et al., 1997; De Clercq, 1995; Pendrak et al., 1994). As part of our ongoing studies on the synthesis and characterization of new heterocyclic systems containing an isoindolinone moiety (Mukherjee et al., 2000; Kundu, Khan & Mukhopadhyay, 1999), the structure determination of (Z)-3-acetonylidene-2,3-dihydro-1H-isoindolin-1-one, (I), was undertaken.

The two approximately parallel molecules (A and B) in the asymmetric unit related by a pseudo-inversion centre at (1/2, 0.38, 1/4), can be described as an N—H···O bonded dimer (Fig. 1). The dihedral angle between the nearly planar molecules A and B is 2.45 (2)°. The Z configuration of the molecules are established by the N1—C8—C9—C10 torsion angles of -4.6 (2)° in A and 4.3 (2)° in B. The angles between the five- and six-membered rings of the isoindolinone system in A and B are 1.92 (6) and 1.54 (6)°, respectively. The bond distances and angles in (I) are similar to those reported for substituted isoindoline structures (Kundu, Khan, Guha & Mukherjee, 1999; Khan et al., 1998; McNab et al., 1997). In the solid state, weak intermolecular C9—H9···O1 hydrogen bonds link the dimers to form infinite chains which are cross-linked in the c direction by weak intermolecular C4B—H4B···O2A hydrogen bonds (Table 2), to form a network.

S2. Experimental

2-[(Trimethylsilyl)ethynyl]benzamide (TEB) was prepared by stirring a mixture of o-iodobenzamide (1 mmol), (trimethylsilyl)acetylene (2 mmol), (PPh₃)₂PdCl₂ (3.5 mol%), CuI (8 mol%) and triethylamine (4 mmol) in dimethylformamide at room temperature under a nitrogen atmosphere for 24 h. The reaction of TEB (1 mmol) with CH₃COCl (acetyl chloride, 1.2 mmol) in the presence of anhydrous AlCl₃ (4 mmol) and tetrachloroethane (10 ml) at 273 K yielded the title compound, (I) (m.p. 381 K). Single crystals suitable for X-ray analysis were obtained by slow crystallization from a dilute solution of (I) in ethanol. Elemental analysis, calculated for C₁₁H₉NO₂: C 70.58, H 4.81, N 7.48%; found: C 70.53, H 4.89, N 7.24%.

S3. Refinement

The H atoms were refined using a riding model and their isotropic displacement parameters were set to 1.2 times (1.5 times for CH₃ groups) the equivalent displacement parameters of their parent atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: MULTAN88 (Debaerdemaeker et al., 1988); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: SHELXL97).

Figures

Fig. 1. ZORTEP view (50% probability level) of the two hydrogen-bonded molecules of (I).

(Z)-3-Acetonylidene-2,3-dihydro-1H-isoindolin-1-one

Crystal data

C11H9NO2	Dx = 1.374 Mg m^−3
Mr = 187.19	Melting point: 381K K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.8673 (2) Å	Cell parameters from 922 reflections
b = 12.8243 (3) Å	θ = 5.4–31.7°
c = 20.6130 (5) Å	µ = 0.10 mm^−1
β = 94.520 (1)°	T = 293 K
V = 1809.71 (8) Å^3	Hexagonal block, colourless
Z = 8	0.50 × 0.45 × 0.30 mm
F(000) = 784

Data collection

Bruker SMART-CCD diffractometer	4172 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 29.5°, θmin = 1.9°
ω scans	h = −9→9
14180 measured reflections	k = −17→17
4883 independent reflections	l = −19→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.6557P] where P = (Fo^2 + 2Fc^2)/3
4883 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.40859 (13)	0.35498 (6)	0.31497 (4)	0.02396 (19)
O2A	0.33134 (15)	0.20346 (7)	0.10029 (5)	0.0297 (2)
N1A	0.38726 (14)	0.22831 (7)	0.23425 (5)	0.0195 (2)
H1A	0.3915	0.2686	0.2010	0.023*
C1A	0.39536 (16)	0.26384 (8)	0.29782 (6)	0.0189 (2)
C2A	0.38352 (15)	0.16893 (8)	0.33865 (6)	0.0181 (2)
C3A	0.37951 (16)	0.16001 (9)	0.40544 (6)	0.0223 (2)
H3A	0.3859	0.2184	0.4323	0.027*
C4A	0.36540 (17)	0.05950 (10)	0.43089 (6)	0.0256 (3)
H4A	0.3608	0.0507	0.4755	0.031*
C5A	0.35806 (17)	−0.02797 (10)	0.39027 (6)	0.0256 (3)
H5A	0.3502	−0.0940	0.4085	0.031*
C6A	0.36229 (17)	−0.01821 (9)	0.32289 (6)	0.0221 (2)
H6A	0.3576	−0.0764	0.2959	0.026*
C7A	0.37386 (15)	0.08210 (8)	0.29771 (5)	0.0180 (2)
C8A	0.37139 (15)	0.12019 (8)	0.23004 (5)	0.0181 (2)
C9A	0.34699 (17)	0.06292 (9)	0.17497 (6)	0.0210 (2)
H9A	0.3478	−0.0094	0.1786	0.025*
C10A	0.31921 (17)	0.10896 (10)	0.10969 (6)	0.0230 (2)
C11A	0.2705 (2)	0.03339 (11)	0.05472 (6)	0.0305 (3)
H11A	0.2261	0.0713	0.0162	0.046*
H11B	0.1696	−0.0132	0.0664	0.046*
H11C	0.3849	−0.0060	0.0466	0.046*
O1B	0.60061 (13)	0.40219 (6)	0.16643 (4)	0.02467 (19)
O2B	0.67865 (14)	0.54109 (7)	0.38522 (4)	0.0288 (2)
N1B	0.62001 (14)	0.52358 (7)	0.25031 (5)	0.0195 (2)
H1B	0.6194	0.4809	0.2825	0.023*
C1B	0.61157 (16)	0.49231 (9)	0.18577 (6)	0.0191 (2)
C2B	0.61878 (16)	0.59041 (9)	0.14732 (6)	0.0191 (2)
C3B	0.61986 (17)	0.60550 (10)	0.08076 (6)	0.0233 (2)
H3B	0.6151	0.5493	0.0521	0.028*
C4B	0.62839 (18)	0.70799 (10)	0.05812 (6)	0.0268 (3)
H4B	0.6299	0.7206	0.0137	0.032*
C5B	0.63468 (18)	0.79181 (10)	0.10166 (7)	0.0271 (3)
H5B	0.6405	0.8594	0.0856	0.033*
C6B	0.63251 (17)	0.77652 (9)	0.16850 (6)	0.0230 (2)
H6B	0.6358	0.8326	0.1972	0.028*
C7B	0.62526 (15)	0.67412 (8)	0.19077 (6)	0.0189 (2)
C8B	0.62954 (15)	0.63147 (8)	0.25736 (6)	0.0185 (2)
C9B	0.64692 (16)	0.68553 (9)	0.31378 (6)	0.0207 (2)
H9B	0.6428	0.7579	0.3117	0.025*
C10B	0.67191 (17)	0.63633 (9)	0.37822 (6)	0.0224 (2)
C11B	0.6919 (2)	0.70922 (10)	0.43578 (6)	0.0292 (3)
H11D	0.7435	0.6717	0.4736	0.044*
H11E	0.5660	0.7372	0.4434	0.044*
H11F	0.7788	0.7652	0.4269	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0275 (4)	0.0155 (4)	0.0293 (4)	0.0007 (3)	0.0052 (3)	−0.0014 (3)
O2A	0.0388 (5)	0.0261 (4)	0.0243 (4)	−0.0040 (4)	0.0025 (4)	0.0043 (3)
N1A	0.0226 (5)	0.0154 (4)	0.0207 (5)	−0.0006 (3)	0.0031 (4)	0.0028 (3)
C1A	0.0158 (5)	0.0174 (5)	0.0236 (5)	0.0014 (4)	0.0026 (4)	0.0018 (4)
C2A	0.0149 (5)	0.0168 (5)	0.0225 (5)	0.0004 (4)	0.0013 (4)	0.0025 (4)
C3A	0.0193 (5)	0.0259 (6)	0.0215 (5)	0.0006 (4)	0.0004 (4)	0.0012 (4)
C4A	0.0219 (5)	0.0316 (6)	0.0230 (5)	0.0006 (5)	−0.0003 (4)	0.0081 (5)
C5A	0.0221 (5)	0.0234 (5)	0.0308 (6)	0.0000 (4)	−0.0004 (4)	0.0112 (5)
C6A	0.0195 (5)	0.0176 (5)	0.0289 (6)	−0.0004 (4)	0.0012 (4)	0.0036 (4)
C7A	0.0149 (5)	0.0174 (5)	0.0215 (5)	0.0002 (4)	0.0009 (4)	0.0026 (4)
C8A	0.0155 (5)	0.0159 (5)	0.0232 (5)	−0.0003 (4)	0.0028 (4)	0.0018 (4)
C9A	0.0217 (5)	0.0181 (5)	0.0236 (5)	−0.0017 (4)	0.0038 (4)	0.0002 (4)
C10A	0.0218 (5)	0.0262 (6)	0.0214 (5)	−0.0017 (4)	0.0049 (4)	−0.0005 (4)
C11A	0.0365 (7)	0.0324 (7)	0.0232 (6)	−0.0009 (5)	0.0059 (5)	−0.0053 (5)
O1B	0.0290 (4)	0.0164 (4)	0.0290 (4)	0.0008 (3)	0.0052 (3)	−0.0016 (3)
O2B	0.0385 (5)	0.0223 (4)	0.0255 (4)	−0.0010 (4)	0.0024 (4)	0.0021 (3)
N1B	0.0226 (5)	0.0141 (4)	0.0217 (5)	−0.0001 (3)	0.0017 (3)	0.0023 (3)
C1B	0.0168 (5)	0.0165 (5)	0.0241 (5)	0.0006 (4)	0.0027 (4)	0.0015 (4)
C2B	0.0157 (5)	0.0176 (5)	0.0238 (5)	−0.0001 (4)	0.0009 (4)	0.0025 (4)
C3B	0.0195 (5)	0.0268 (6)	0.0237 (6)	−0.0007 (4)	0.0009 (4)	0.0015 (4)
C4B	0.0219 (6)	0.0330 (6)	0.0254 (6)	−0.0006 (5)	0.0004 (4)	0.0093 (5)
C5B	0.0244 (6)	0.0228 (6)	0.0338 (7)	−0.0003 (4)	0.0007 (5)	0.0111 (5)
C6B	0.0212 (5)	0.0166 (5)	0.0311 (6)	−0.0009 (4)	0.0005 (4)	0.0039 (4)
C7B	0.0150 (5)	0.0170 (5)	0.0244 (5)	−0.0009 (4)	0.0004 (4)	0.0030 (4)
C8B	0.0149 (5)	0.0154 (5)	0.0251 (5)	−0.0003 (4)	0.0009 (4)	0.0029 (4)
C9B	0.0200 (5)	0.0172 (5)	0.0250 (5)	−0.0009 (4)	0.0020 (4)	0.0004 (4)
C10B	0.0201 (5)	0.0235 (5)	0.0235 (5)	−0.0011 (4)	0.0020 (4)	−0.0004 (4)
C11B	0.0343 (7)	0.0286 (6)	0.0246 (6)	0.0014 (5)	0.0012 (5)	−0.0046 (5)

Geometric parameters (Å, º)

O1A—C1A	1.2224 (14)	O1B—C1B	1.2229 (14)
O2A—C10A	1.2312 (15)	O2B—C10B	1.2302 (15)
N1A—C1A	1.3842 (15)	N1B—C1B	1.3863 (15)
N1A—C8A	1.3931 (14)	N1B—C8B	1.3923 (13)
N1A—H1A	0.8600	N1B—H1B	0.8600
C1A—C2A	1.4857 (15)	C1B—C2B	1.4898 (15)
C2A—C3A	1.3840 (16)	C2B—C3B	1.3862 (16)
C2A—C7A	1.3955 (15)	C2B—C7B	1.3965 (16)
C3A—C4A	1.3979 (17)	C3B—C4B	1.3975 (17)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.3982 (19)	C4B—C5B	1.3989 (19)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.3972 (17)	C5B—C6B	1.3929 (18)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.3918 (15)	C6B—C7B	1.3934 (15)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.4768 (15)	C7B—C8B	1.4757 (15)
C8A—C9A	1.3513 (16)	C8B—C9B	1.3512 (16)
C9A—C10A	1.4682 (16)	C9B—C10B	1.4682 (16)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.5082 (17)	C10B—C11B	1.5083 (17)
C11A—H11A	0.9600	C11B—H11D	0.9600
C11A—H11B	0.9600	C11B—H11E	0.9600
C11A—H11C	0.9600	C11B—H11F	0.9600
C1A—N1A—C8A	112.57 (9)	C1B—N1B—C8B	112.68 (9)
C1A—N1A—H1A	123.7	C1B—N1B—H1B	123.7
C8A—N1A—H1A	123.7	C8B—N1B—H1B	123.7
O1A—C1A—N1A	125.81 (10)	O1B—C1B—N1B	125.66 (10)
O1A—C1A—C2A	128.73 (11)	O1B—C1B—C2B	128.93 (11)
N1A—C1A—C2A	105.46 (9)	N1B—C1B—C2B	105.41 (9)
C3A—C2A—C7A	122.13 (10)	C3B—C2B—C7B	121.67 (10)
C3A—C2A—C1A	129.61 (10)	C3B—C2B—C1B	130.35 (11)
C7A—C2A—C1A	108.26 (10)	C7B—C2B—C1B	107.98 (10)
C2A—C3A—C4A	117.19 (11)	C2B—C3B—C4B	117.74 (11)
C2A—C3A—H3A	121.4	C2B—C3B—H3B	121.1
C4A—C3A—H3A	121.4	C4B—C3B—H3B	121.1
C3A—C4A—C5A	121.02 (11)	C3B—C4B—C5B	120.56 (11)
C3A—C4A—H4A	119.5	C3B—C4B—H4B	119.7
C5A—C4A—H4A	119.5	C5B—C4B—H4B	119.7
C6A—C5A—C4A	121.38 (11)	C6B—C5B—C4B	121.62 (11)
C6A—C5A—H5A	119.3	C6B—C5B—H5B	119.2
C4A—C5A—H5A	119.3	C4B—C5B—H5B	119.2
C7A—C6A—C5A	117.37 (11)	C5B—C6B—C7B	117.52 (11)
C7A—C6A—H6A	121.3	C5B—C6B—H6B	121.2
C5A—C6A—H6A	121.3	C7B—C6B—H6B	121.2
C6A—C7A—C2A	120.89 (11)	C6B—C7B—C2B	120.89 (11)
C6A—C7A—C8A	131.39 (10)	C6B—C7B—C8B	131.08 (11)
C2A—C7A—C8A	107.68 (9)	C2B—C7B—C8B	107.99 (9)
C9A—C8A—N1A	126.67 (10)	C9B—C8B—N1B	126.87 (11)
C9A—C8A—C7A	127.24 (10)	C9B—C8B—C7B	127.19 (10)
N1A—C8A—C7A	105.98 (9)	N1B—C8B—C7B	105.90 (9)
C8A—C9A—C10A	123.37 (11)	C8B—C9B—C10B	123.66 (11)
C8A—C9A—H9A	118.3	C8B—C9B—H9B	118.2
C10A—C9A—H9A	118.3	C10B—C9B—H9B	118.2
O2A—C10A—C9A	122.31 (11)	O2B—C10B—C9B	122.23 (11)
O2A—C10A—C11A	121.87 (11)	O2B—C10B—C11B	121.52 (11)
C9A—C10A—C11A	115.80 (11)	C9B—C10B—C11B	116.24 (11)
C10A—C11A—H11A	109.5	C10B—C11B—H11D	109.5
C10A—C11A—H11B	109.5	C10B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
C10A—C11A—H11C	109.5	C10B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
C8A—N1A—C1A—O1A	−179.69 (10)	C8B—N1B—C1B—O1B	−179.29 (11)
C8A—N1A—C1A—C2A	0.01 (12)	C8B—N1B—C1B—C2B	0.72 (12)
O1A—C1A—C2A—C3A	1.8 (2)	O1B—C1B—C2B—C3B	−1.8 (2)
N1A—C1A—C2A—C3A	−177.86 (11)	N1B—C1B—C2B—C3B	178.21 (11)
O1A—C1A—C2A—C7A	−178.89 (11)	O1B—C1B—C2B—C7B	178.31 (11)
N1A—C1A—C2A—C7A	1.42 (12)	N1B—C1B—C2B—C7B	−1.71 (12)
C7A—C2A—C3A—C4A	0.05 (17)	C7B—C2B—C3B—C4B	0.22 (17)
C1A—C2A—C3A—C4A	179.25 (11)	C1B—C2B—C3B—C4B	−179.69 (11)
C2A—C3A—C4A—C5A	0.74 (17)	C2B—C3B—C4B—C5B	−0.28 (17)
C3A—C4A—C5A—C6A	−0.74 (18)	C3B—C4B—C5B—C6B	−0.06 (19)
C4A—C5A—C6A—C7A	−0.08 (17)	C4B—C5B—C6B—C7B	0.46 (18)
C5A—C6A—C7A—C2A	0.86 (16)	C5B—C6B—C7B—C2B	−0.52 (17)
C5A—C6A—C7A—C8A	−176.59 (11)	C5B—C6B—C7B—C8B	177.08 (11)
C3A—C2A—C7A—C6A	−0.87 (17)	C3B—C2B—C7B—C6B	0.19 (17)
C1A—C2A—C7A—C6A	179.78 (10)	C1B—C2B—C7B—C6B	−179.89 (10)
C3A—C2A—C7A—C8A	177.13 (10)	C3B—C2B—C7B—C8B	−177.91 (10)
C1A—C2A—C7A—C8A	−2.23 (12)	C1B—C2B—C7B—C8B	2.01 (12)
C1A—N1A—C8A—C9A	175.11 (11)	C1B—N1B—C8B—C9B	−177.17 (11)
C1A—N1A—C8A—C7A	−1.34 (12)	C1B—N1B—C8B—C7B	0.48 (12)
C6A—C7A—C8A—C9A	3.5 (2)	C6B—C7B—C8B—C9B	−1.8 (2)
C2A—C7A—C8A—C9A	−174.22 (11)	C2B—C7B—C8B—C9B	176.06 (11)
C6A—C7A—C8A—N1A	179.91 (11)	C6B—C7B—C8B—N1B	−179.41 (11)
C2A—C7A—C8A—N1A	2.20 (12)	C2B—C7B—C8B—N1B	−1.57 (12)
N1A—C8A—C9A—C10A	−4.56 (18)	N1B—C8B—C9B—C10B	4.26 (18)
C7A—C8A—C9A—C10A	171.14 (10)	C7B—C8B—C9B—C10B	−172.90 (10)
C8A—C9A—C10A—O2A	5.77 (19)	C8B—C9B—C10B—O2B	−0.05 (18)
C8A—C9A—C10A—C11A	−172.99 (11)	C8B—C9B—C10B—C11B	179.11 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2A	0.86	2.25	2.776 (1)	120
N1A—H1A···O1B	0.86	2.38	3.065 (1)	137
N1B—H1B···O1A	0.86	2.30	2.977 (1)	135
N1B—H1B···O2B	0.86	2.26	2.787 (1)	120
C9A—H9A···O1A^i	0.93	2.49	3.208 (1)	135
C4B—H4B···O2A^ii	0.93	2.58	3.488 (2)	167
C9B—H9B···O1B^iii	0.93	2.57	3.283 (1)	134

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