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The title compound, C
11H
8O
3, displays catemeric aggregation, involving hydrogen bonds progressing from the carboxyl of one molecule to the ketone of a glide-related neighbor [O
O = 2.6952 (12) Å and O—H
O = 177.7 (16)°]. The molecule is highly planar and inherently achiral, but a slight conformational enantiomerism generated by the packing creates alternating conformational chirality in the chain units. Hydrogen-bonding chains, all aligned in the
a-axis direction, occur in parallel counter-directional pairs related by centrosymmetry. Significant overlap of the aromatic rings occurs in the molecular stacking, at an average distance of 3.354 Å. Two C—H
O=C close contacts exist.
Supporting information
CCDC reference: 647271
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.033
- wR factor = 0.091
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C1 .. 5.20 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2004); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(
E)-(1-Oxoindan-2-ylidene)acetic acid
top
Crystal data top
C11H8O3 | Dx = 1.460 Mg m−3 |
Mr = 188.17 | Melting point: 483 K |
Orthorhombic, Pbcn | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 9727 reflections |
a = 14.9634 (2) Å | θ = 5.6–67.9° |
b = 7.1821 (1) Å | µ = 0.89 mm−1 |
c = 15.9359 (2) Å | T = 100 K |
V = 1712.61 (4) Å3 | Block, light yellow |
Z = 8 | 0.26 × 0.26 × 0.16 mm |
F(000) = 784 | |
Data collection top
Bruker SMART CCD APEXII area-detector diffractometer | 1548 independent reflections |
Radiation source: fine-focus sealed tube | 1473 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 67.9°, θmin = 5.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −17→17 |
Tmin = 0.802, Tmax = 0.871 | k = −8→8 |
9720 measured reflections | l = −19→18 |
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)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.6492P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1548 reflections | Δρmax = 0.26 e Å−3 |
131 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0017 (3) |
Special details top
Experimental. crystal mounted on cryoloop using Paratone-N |
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 | Uiso*/Ueq | |
O1 | 0.69765 (6) | 0.22077 (12) | 0.55161 (5) | 0.0212 (2) | |
C1 | 0.74819 (8) | 0.16486 (15) | 0.60691 (7) | 0.0172 (3) | |
C2 | 0.84824 (8) | 0.16378 (15) | 0.60089 (7) | 0.0172 (3) | |
O2 | 1.03870 (6) | 0.16788 (13) | 0.57946 (5) | 0.0258 (3) | |
O3 | 1.01774 (6) | 0.29483 (13) | 0.45257 (5) | 0.0236 (2) | |
H3C | 1.0787 (13) | 0.289 (2) | 0.4526 (10) | 0.035* | |
C3A | 0.80285 (8) | 0.04851 (15) | 0.73346 (7) | 0.0178 (3) | |
C3 | 0.88559 (8) | 0.08512 (16) | 0.68159 (7) | 0.0188 (3) | |
H3A | 0.9254 | 0.1759 | 0.7096 | 0.023* | |
H3B | 0.9192 | −0.0314 | 0.6712 | 0.023* | |
C4 | 0.79747 (8) | −0.01894 (16) | 0.81539 (7) | 0.0205 (3) | |
H4A | 0.8501 | −0.0463 | 0.8464 | 0.025* | |
C5 | 0.71367 (9) | −0.04506 (17) | 0.85047 (8) | 0.0226 (3) | |
H5A | 0.7091 | −0.0929 | 0.9059 | 0.027* | |
C6 | 0.63548 (9) | −0.00242 (17) | 0.80602 (8) | 0.0225 (3) | |
H6A | 0.5789 | −0.0211 | 0.8317 | 0.027* | |
C7A | 0.72490 (8) | 0.09073 (15) | 0.68958 (7) | 0.0174 (3) | |
C7 | 0.64006 (8) | 0.06651 (16) | 0.72522 (7) | 0.0196 (3) | |
H7A | 0.5874 | 0.0965 | 0.6948 | 0.024* | |
C8 | 0.89050 (8) | 0.22630 (16) | 0.53244 (7) | 0.0185 (3) | |
H8A | 0.8561 | 0.2728 | 0.4869 | 0.022* | |
C9 | 0.98920 (8) | 0.22526 (15) | 0.52537 (7) | 0.0187 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0159 (5) | 0.0298 (5) | 0.0179 (4) | 0.0013 (3) | −0.0019 (3) | 0.0022 (3) |
C1 | 0.0171 (6) | 0.0170 (5) | 0.0175 (5) | −0.0003 (4) | 0.0000 (4) | −0.0030 (4) |
C2 | 0.0160 (6) | 0.0176 (5) | 0.0180 (6) | 0.0003 (4) | −0.0013 (4) | −0.0025 (4) |
O2 | 0.0159 (4) | 0.0374 (5) | 0.0240 (5) | 0.0006 (4) | −0.0015 (3) | 0.0062 (4) |
O3 | 0.0158 (5) | 0.0344 (5) | 0.0207 (5) | −0.0002 (4) | 0.0022 (3) | 0.0039 (4) |
C3A | 0.0198 (6) | 0.0152 (5) | 0.0186 (6) | −0.0007 (4) | −0.0007 (4) | −0.0037 (4) |
C3 | 0.0168 (6) | 0.0209 (6) | 0.0186 (6) | 0.0001 (5) | −0.0014 (4) | −0.0005 (4) |
C4 | 0.0242 (6) | 0.0189 (6) | 0.0185 (6) | −0.0003 (5) | −0.0040 (5) | −0.0015 (4) |
C5 | 0.0316 (7) | 0.0201 (6) | 0.0162 (6) | −0.0016 (5) | 0.0024 (5) | −0.0004 (4) |
C6 | 0.0236 (6) | 0.0216 (6) | 0.0222 (6) | −0.0023 (5) | 0.0057 (5) | −0.0013 (5) |
C7A | 0.0191 (6) | 0.0158 (5) | 0.0172 (6) | −0.0001 (4) | −0.0004 (4) | −0.0025 (4) |
C7 | 0.0181 (6) | 0.0198 (6) | 0.0210 (6) | −0.0005 (4) | 0.0008 (5) | −0.0015 (4) |
C8 | 0.0172 (6) | 0.0204 (6) | 0.0178 (6) | 0.0012 (4) | −0.0021 (4) | −0.0010 (4) |
C9 | 0.0191 (6) | 0.0184 (6) | 0.0188 (6) | −0.0010 (4) | 0.0006 (5) | −0.0015 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.2288 (15) | C3—H3B | 0.9900 |
C1—C7A | 1.4630 (16) | C4—C5 | 1.3857 (18) |
C1—C2 | 1.5003 (16) | C4—H4A | 0.9500 |
C2—C8 | 1.3384 (17) | C5—C6 | 1.4016 (18) |
C2—C3 | 1.5117 (16) | C5—H5A | 0.9500 |
O2—C9 | 1.2089 (15) | C6—C7 | 1.3812 (17) |
O3—C9 | 1.3333 (14) | C6—H6A | 0.9500 |
O3—H3C | 0.91 (2) | C7A—C7 | 1.4016 (17) |
C3A—C7A | 1.3934 (17) | C7—H7A | 0.9500 |
C3A—C4 | 1.3949 (17) | C8—C9 | 1.4812 (17) |
C3A—C3 | 1.5118 (16) | C8—H8A | 0.9500 |
C3—H3A | 0.9900 | | |
| | | |
O1—C1—C7A | 128.18 (11) | C4—C5—C6 | 121.46 (11) |
O1—C1—C2 | 124.75 (10) | C4—C5—H5A | 119.3 |
C7A—C1—C2 | 107.06 (10) | C6—C5—H5A | 119.3 |
C8—C2—C1 | 121.46 (10) | C7—C6—C5 | 120.54 (12) |
C8—C2—C3 | 130.09 (11) | C7—C6—H6A | 119.7 |
C1—C2—C3 | 108.45 (9) | C5—C6—H6A | 119.7 |
C9—O3—H3C | 107.6 (10) | C3A—C7A—C7 | 121.85 (11) |
C7A—C3A—C4 | 119.81 (11) | C3A—C7A—C1 | 109.38 (11) |
C7A—C3A—C3 | 111.92 (10) | C7—C7A—C1 | 128.74 (11) |
C4—C3A—C3 | 128.27 (11) | C6—C7—C7A | 117.85 (12) |
C2—C3—C3A | 103.14 (9) | C6—C7—H7A | 121.1 |
C2—C3—H3A | 111.1 | C7A—C7—H7A | 121.1 |
C3A—C3—H3A | 111.1 | C2—C8—C9 | 122.10 (11) |
C2—C3—H3B | 111.1 | C2—C8—H8A | 118.9 |
C3A—C3—H3B | 111.1 | C9—C8—H8A | 118.9 |
H3A—C3—H3B | 109.1 | O2—C9—O3 | 123.49 (12) |
C5—C4—C3A | 118.47 (11) | O2—C9—C8 | 123.94 (11) |
C5—C4—H4A | 120.8 | O3—C9—C8 | 112.56 (10) |
C3A—C4—H4A | 120.8 | | |
| | | |
O1—C1—C2—C8 | 0.14 (17) | C4—C3A—C7A—C1 | 177.93 (10) |
C7A—C1—C2—C8 | −179.12 (10) | C3—C3A—C7A—C1 | −2.11 (13) |
O1—C1—C2—C3 | 179.88 (11) | O1—C1—C7A—C3A | −178.34 (11) |
C7A—C1—C2—C3 | 0.62 (12) | C2—C1—C7A—C3A | 0.89 (12) |
C8—C2—C3—C3A | 177.97 (12) | O1—C1—C7A—C7 | −0.2 (2) |
C1—C2—C3—C3A | −1.73 (11) | C2—C1—C7A—C7 | 179.02 (11) |
C7A—C3A—C3—C2 | 2.38 (13) | C5—C6—C7—C7A | 0.42 (17) |
C4—C3A—C3—C2 | −177.65 (11) | C3A—C7A—C7—C6 | −0.40 (17) |
C7A—C3A—C4—C5 | 1.07 (17) | C1—C7A—C7—C6 | −178.32 (11) |
C3—C3A—C4—C5 | −178.89 (11) | C1—C2—C8—C9 | −179.68 (10) |
C3A—C4—C5—C6 | −1.06 (18) | C3—C2—C8—C9 | 0.64 (19) |
C4—C5—C6—C7 | 0.31 (18) | C2—C8—C9—O2 | 0.52 (18) |
C4—C3A—C7A—C7 | −0.36 (17) | C2—C8—C9—O3 | −179.45 (10) |
C3—C3A—C7A—C7 | 179.61 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3C···O1i | 0.91 (2) | 1.78 (2) | 2.6952 (12) | 177.7 (16) |
C4—H4A···O2ii | 0.95 | 2.56 | 3.2584 (15) | 131 |
C5—H5A···O1iii | 0.95 | 2.50 | 3.4531 (15) | 180 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+2, y, −z+3/2; (iii) x, −y, z+1/2. |
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