1-Oxoindan-6-carboxylic acid: catemeric hydrogen bonding in an aromatic δ-keto acid

The title compound, C₁₀H₈O₃, aggregates in the crystal structure as catemers, whose hydrogen bonding progresses from the carboxyl to the ketone of a neighboring screw-related mol­ecule along the b axis [O...O = 2.6481 (12) Å and O—H...O = 169°]. Four hydrogen-bonding chains in centrosymmetric pairs pass through the cell in the b-axis direction. Two inter­molecular C—H...O=C close contacts are found, involving both the ketone and acid functions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.094
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      64.79 Deg.

Author Response: diffrn reflns theta full (too) Low...64.79\%. (Alert level A) and resolution (too) Low [sin\q/\l < 0.6] (Alert level C): this problem has arisen because initially we were told by the manufacturer of our newly installed Bruker Smart Apex II unit to collect our small-molecule data to 0.85\%A resolution (with copper K\a radiation). This yields a \q max. of ca. 64.79\%, less than the 67\% required by Acta.

Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5868
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      64.79 Deg.

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker,2000); cell refinement: SAINT-Plus (Bruker,2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker,2000); software used to prepare material for publication: SHELXTL.

1-Oxoindan-6-carboxylic acid

Crystal data

C10H8O3	F(000) = 368
Mr = 176.16	Dx = 1.489 Mg m^−3
Monoclinic, P21/c	Melting point: 533 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 6.6457 (1) Å	Cell parameters from 4303 reflections
b = 17.4657 (3) Å	θ = 5.1–64.8°
c = 7.0105 (1) Å	µ = 0.93 mm^−1
β = 105.068 (1)°	T = 100 K
V = 785.74 (2) Å^3	Block, colourless
Z = 4	0.25 × 0.22 × 0.15 mm

Data collection

Bruker SMART CCD APEX-II area-detector diffractometer	1273 independent reflections
Radiation source: fine-focus sealed tube	1241 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
φ and ω scans	θmax = 64.8°, θmin = 5.1°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −7→7
Tmin = 0.799, Tmax = 0.874	k = −20→20
4303 measured reflections	l = −7→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 0.2662P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1273 reflections	Δρmax = 0.23 e Å^−3
120 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O3	0.21914 (14)	0.49240 (5)	0.81019 (14)	0.0254 (3)
H3	0.1410	0.5310	0.7904	0.038*
O1	−0.01396 (13)	0.12364 (5)	0.76269 (14)	0.0241 (3)
O2	−0.07920 (14)	0.43110 (5)	0.80164 (14)	0.0254 (3)
C7	0.1282 (2)	0.28876 (7)	0.81580 (18)	0.0178 (3)
H7	−0.0197	0.2870	0.7765	0.021*
C6	0.2326 (2)	0.35820 (7)	0.84571 (18)	0.0178 (3)
C3A	0.4618 (2)	0.22219 (7)	0.90479 (18)	0.0182 (3)
C5	0.4521 (2)	0.35944 (7)	0.90336 (18)	0.0196 (3)
H5	0.5229	0.4072	0.9211	0.024*
C7A	0.2449 (2)	0.22175 (7)	0.84457 (18)	0.0173 (3)
C8	0.1064 (2)	0.43009 (7)	0.81709 (18)	0.0186 (3)
C4	0.56642 (19)	0.29221 (7)	0.93465 (18)	0.0201 (3)
H4	0.7143	0.2937	0.9760	0.024*
C2	0.35630 (19)	0.08958 (7)	0.87338 (18)	0.0205 (3)
H2A	0.3602	0.0559	0.7608	0.025*
H2B	0.3507	0.0572	0.9878	0.025*
C3	0.54913 (19)	0.14201 (7)	0.92576 (19)	0.0208 (3)
H3A	0.6330	0.1325	1.0626	0.025*
H3B	0.6379	0.1335	0.8341	0.025*
C1	0.16934 (19)	0.14230 (7)	0.81897 (18)	0.0183 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0218 (5)	0.0133 (5)	0.0421 (6)	0.0004 (3)	0.0099 (4)	0.0007 (4)
O1	0.0184 (5)	0.0160 (5)	0.0370 (6)	−0.0013 (3)	0.0059 (4)	−0.0011 (4)
O2	0.0189 (5)	0.0178 (5)	0.0377 (6)	0.0008 (3)	0.0039 (4)	−0.0008 (4)
C7	0.0163 (6)	0.0189 (7)	0.0179 (6)	0.0002 (5)	0.0042 (5)	0.0003 (4)
C6	0.0209 (7)	0.0172 (7)	0.0159 (6)	0.0012 (5)	0.0057 (5)	0.0002 (4)
C3A	0.0193 (7)	0.0203 (7)	0.0153 (6)	0.0014 (5)	0.0049 (5)	0.0002 (4)
C5	0.0211 (7)	0.0181 (7)	0.0196 (6)	−0.0038 (5)	0.0052 (5)	−0.0018 (5)
C7A	0.0185 (6)	0.0180 (7)	0.0157 (6)	0.0005 (5)	0.0053 (5)	0.0004 (4)
C8	0.0206 (7)	0.0166 (6)	0.0177 (6)	−0.0014 (5)	0.0032 (5)	−0.0017 (4)
C4	0.0157 (6)	0.0231 (7)	0.0212 (7)	−0.0002 (5)	0.0040 (5)	−0.0008 (5)
C2	0.0220 (7)	0.0165 (6)	0.0231 (7)	0.0025 (5)	0.0063 (5)	0.0011 (5)
C3	0.0191 (7)	0.0196 (7)	0.0232 (7)	0.0033 (5)	0.0049 (5)	0.0003 (5)
C1	0.0204 (7)	0.0169 (7)	0.0186 (6)	0.0008 (5)	0.0069 (5)	0.0003 (4)

Geometric parameters (Å, º)

O3—C8	1.3290 (15)	C3A—C3	1.5083 (17)
O3—H3	0.8400	C5—C4	1.3848 (18)
O1—C1	1.2231 (16)	C5—H5	0.9500
O2—C8	1.2103 (16)	C7A—C1	1.4708 (17)
C7—C6	1.3859 (17)	C4—H4	0.9500
C7—C7A	1.3897 (17)	C2—C1	1.5135 (17)
C7—H7	0.9500	C2—C3	1.5398 (17)
C6—C5	1.4088 (19)	C2—H2A	0.9900
C6—C8	1.4941 (17)	C2—H2B	0.9900
C3A—C7A	1.3923 (19)	C3—H3A	0.9900
C3A—C4	1.3956 (18)	C3—H3B	0.9900
C8—O3—H3	109.5	C5—C4—C3A	119.20 (12)
C6—C7—C7A	118.45 (12)	C5—C4—H4	120.4
C6—C7—H7	120.8	C3A—C4—H4	120.4
C7A—C7—H7	120.8	C1—C2—C3	106.02 (10)
C7—C6—C5	119.81 (11)	C1—C2—H2A	110.5
C7—C6—C8	118.27 (11)	C3—C2—H2A	110.5
C5—C6—C8	121.92 (11)	C1—C2—H2B	110.5
C7A—C3A—C4	119.10 (11)	C3—C2—H2B	110.5
C7A—C3A—C3	111.48 (10)	H2A—C2—H2B	108.7
C4—C3A—C3	129.41 (12)	C3A—C3—C2	104.69 (10)
C4—C5—C6	121.13 (11)	C3A—C3—H3A	110.8
C4—C5—H5	119.4	C2—C3—H3A	110.8
C6—C5—H5	119.4	C3A—C3—H3B	110.8
C7—C7A—C3A	122.29 (11)	C2—C3—H3B	110.8
C7—C7A—C1	128.08 (11)	H3A—C3—H3B	108.9
C3A—C7A—C1	109.63 (10)	O1—C1—C7A	124.80 (11)
O2—C8—O3	123.77 (11)	O1—C1—C2	127.07 (11)
O2—C8—C6	123.21 (11)	C7A—C1—C2	108.13 (10)
O3—C8—C6	113.02 (11)
C7A—C7—C6—C5	0.18 (19)	C5—C6—C8—O3	13.36 (17)
C7A—C7—C6—C8	−179.24 (10)	C6—C5—C4—C3A	1.21 (19)
C7—C6—C5—C4	−1.26 (19)	C7A—C3A—C4—C5	−0.11 (19)
C8—C6—C5—C4	178.14 (11)	C3—C3A—C4—C5	179.08 (12)
C6—C7—C7A—C3A	0.93 (19)	C7A—C3A—C3—C2	−0.89 (14)
C6—C7—C7A—C1	−178.96 (11)	C4—C3A—C3—C2	179.87 (12)
C4—C3A—C7A—C7	−1.0 (2)	C1—C2—C3—C3A	1.76 (13)
C3—C3A—C7A—C7	179.70 (11)	C7—C7A—C1—O1	1.6 (2)
C4—C3A—C7A—C1	178.93 (10)	C3A—C7A—C1—O1	−178.27 (12)
C3—C3A—C7A—C1	−0.39 (15)	C7—C7A—C1—C2	−178.54 (12)
C7—C6—C8—O2	12.68 (19)	C3A—C7A—C1—C2	1.56 (14)
C5—C6—C8—O2	−166.72 (12)	C3—C2—C1—O1	177.78 (13)
C7—C6—C8—O3	−167.23 (10)	C3—C2—C1—C7A	−2.05 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^i	0.84	1.82	2.6481 (12)	169
C3—H3B···O1^ii	0.99	2.50	3.4009 (16)	152
C3—H3A···O2^iii	0.99	2.46	3.3603 (15)	152

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