The asymmetric unit of the title compound, C
11H
9NO
2, 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.
Supporting information
CCDC reference: 165654
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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%.
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.
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).
(
Z)-3-Acetonylidene-2,3-dihydro-1
H-isoindolin-1-one
top
Crystal data top
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) Å3 | Hexagonal block, colourless |
Z = 8 | 0.50 × 0.45 × 0.30 mm |
F(000) = 784 | |
Data collection top
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 top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0603P)2 + 0.6557P] where P = (Fo2 + 2Fc2)/3 |
4883 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Crystal data top
C11H9NO2 | V = 1809.71 (8) Å3 |
Mr = 187.19 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.8673 (2) Å | µ = 0.10 mm−1 |
b = 12.8243 (3) Å | T = 293 K |
c = 20.6130 (5) Å | 0.50 × 0.45 × 0.30 mm |
β = 94.520 (1)° | |
Data collection top
Bruker SMART-CCD diffractometer | 4172 reflections with I > 2σ(I) |
14180 measured reflections | Rint = 0.030 |
4883 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.36 e Å−3 |
4883 reflections | Δρmin = −0.26 e Å−3 |
255 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1Ai | 0.93 | 2.49 | 3.208 (1) | 135 |
C4B—H4B···O2Aii | 0.93 | 2.58 | 3.488 (2) | 167 |
C9B—H9B···O1Biii | 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. |
Experimental details
Crystal data |
Chemical formula | C11H9NO2 |
Mr | 187.19 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 6.8673 (2), 12.8243 (3), 20.6130 (5) |
β (°) | 94.520 (1) |
V (Å3) | 1809.71 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.45 × 0.30 |
|
Data collection |
Diffractometer | Bruker SMART-CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14180, 4883, 4172 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.693 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.121, 1.05 |
No. of reflections | 4883 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.26 |
Selected geometric parameters (Å, º) topN1A—C1A | 1.3842 (15) | N1B—C1B | 1.3863 (15) |
N1A—C8A | 1.3931 (14) | N1B—C8B | 1.3923 (13) |
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) |
| | | |
C1A—N1A—C8A | 112.57 (9) | C1B—N1B—C8B | 112.68 (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) |
| | | |
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) |
Hydrogen-bond geometry (Å, º) top
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···O1Ai | 0.93 | 2.49 | 3.208 (1) | 135 |
C4B—H4B···O2Aii | 0.93 | 2.58 | 3.488 (2) | 167 |
C9B—H9B···O1Biii | 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. |
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.