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The title racemate, C11H16O3, displays two different hydrogen-bonding modes in the crystal structure. The chosen asymmetric unit consists of two mol­ecules of identical handedness that differ in the rotation of their carboxyl groups and are linked by an acid-to-ketone hydrogen bond [O...O = 2.7219 (17) Å and O—H...O = 174°]. The remaining carboxyl forms a centrosymmetric dimer with a second such unit [O...O = 2.6368 (15) Å and O—H...O = 174°], while the ketones at the extremities of this four-mol­ecule aggregate remain unengaged. Five inter­molecular C—H...O close contacts were found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011609/su3004sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011609/su3004Isup2.hkl
Contains datablock I

CCDC reference: 643121

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.106
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
Author Response: _diffrn_measured_fraction_theta_full Low .......0.91. (Alert level A). Even though we collected data out to 0.83 \%A, the crystal diffracted poorly beyond 0.88 \%A resolution, where more than 40% of the missing data lie. Larger crystals were not obtainable, and since the crystals of this compound are no longer available, we can only rely on the current data set.

Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 67.85 From the CIF: _diffrn_reflns_theta_full 67.85 From the CIF: _reflns_number_total 3340 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3657 Completeness (_total/calc) 91.33% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 60 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for O2B - C9B .. 5.52 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 23 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C11 H16 O3 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C11 H16 O3
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS (Sheldrick, 1997); program(s) used to refine structure: SHELXL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2004); software used to prepare material for publication: SHELXTL.

(2S*,4aR*,8aS*)-6-Oxoperhydronaphthalene-2-carboxylic acid top
Crystal data top
C11H16O3Z = 4
Mr = 196.24F(000) = 424
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Melting point: 393 K
a = 7.4089 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 11.3743 (2) ÅCell parameters from 10147 reflections
c = 12.9478 (2) Åθ = 3.7–67.9°
α = 112.6743 (6)°µ = 0.76 mm1
β = 91.9072 (6)°T = 100 K
γ = 90.6949 (6)°Parallelepiped, colourless
V = 1005.87 (3) Å30.33 × 0.19 × 0.14 mm
Data collection top
Bruker SMART CCD APEXII area-detector
diffractometer
3340 independent reflections
Radiation source: fine-focus sealed tube3041 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 67.9°, θmin = 3.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 88
Tmin = 0.790, Tmax = 0.901k = 1313
10147 measured reflectionsl = 1513
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.6443P]
where P = (Fo2 + 2Fc2)/3
3340 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
C1A0.0155 (2)0.51481 (15)0.70850 (14)0.0229 (3)
H1A0.02090.59640.70440.027*
H1B0.12950.48970.66880.027*
O1A0.63304 (17)0.33432 (12)0.49361 (12)0.0400 (3)
C1B1.0437 (2)0.92719 (14)1.30068 (13)0.0213 (3)
H1BA1.12360.86341.24960.026*
H1BB1.01220.89841.36100.026*
O1B0.58059 (14)0.82579 (11)0.93838 (10)0.0257 (3)
C2A0.0485 (2)0.53432 (15)0.83160 (14)0.0233 (3)
H2A0.09690.45300.83240.028*
O2A0.17140 (17)0.71947 (12)0.98523 (10)0.0343 (3)
C2B1.1449 (2)1.05722 (15)1.35218 (14)0.0217 (3)
H2BA1.06461.11971.40590.026*
O2B1.45654 (14)1.01194 (11)1.37686 (9)0.0264 (3)
C3A0.1272 (2)0.55815 (16)0.89392 (14)0.0268 (4)
H3A0.10280.56020.97020.032*
H3B0.17240.64250.90140.032*
O3A0.33489 (16)0.63283 (12)0.83407 (10)0.0337 (3)
H3AA0.40690.69320.87100.051*
C3B1.1915 (2)1.10597 (15)1.26143 (14)0.0235 (4)
H3BA1.27601.04751.20950.028*
H3BB1.25141.19121.29620.028*
O3B1.27197 (15)1.04998 (13)1.51884 (10)0.0309 (3)
H3BC1.36241.02861.54770.046*
C4AA0.3057 (2)0.44284 (15)0.71365 (14)0.0242 (4)
H4AA0.34690.52690.71520.029*
C4A0.2720 (2)0.45675 (16)0.83451 (15)0.0286 (4)
H4A0.38570.47980.87490.034*
H4B0.23400.37410.83570.034*
C4BA0.9145 (2)0.98678 (14)1.14553 (13)0.0202 (3)
H4BC0.99300.92431.09030.024*
C4B1.0175 (2)1.11425 (15)1.19596 (14)0.0233 (4)
H4BA0.93861.17891.24700.028*
H4BB1.04931.14231.13520.028*
C5A0.4562 (2)0.34366 (17)0.65430 (16)0.0313 (4)
H5A0.42410.26090.65770.038*
H5B0.57000.37080.69380.038*
C5B0.7397 (2)0.99760 (15)1.08311 (14)0.0230 (4)
H5BA0.66441.06421.13510.028*
H5BB0.77001.02391.02110.028*
C6A0.4853 (2)0.32697 (15)0.53375 (16)0.0305 (4)
C6B0.6337 (2)0.87311 (15)1.03643 (14)0.0227 (4)
C7A0.3169 (2)0.30065 (18)0.46723 (16)0.0350 (4)
H7A0.34450.30450.39330.042*
H7B0.27680.21360.45440.042*
C7B0.5996 (2)0.81041 (16)1.11719 (14)0.0251 (4)
H7BA0.55190.72241.07540.030*
H7BB0.50730.85801.16980.030*
C8AA0.1314 (2)0.41249 (15)0.64969 (14)0.0232 (4)
H8AA0.08770.32950.64940.028*
C8A0.1638 (2)0.39761 (16)0.52846 (15)0.0278 (4)
H8A0.05100.37000.48800.033*
H8B0.19390.48150.52690.033*
C8BA0.8718 (2)0.93585 (14)1.23595 (13)0.0203 (3)
H8BC0.78990.99681.28980.024*
C8B0.7740 (2)0.80643 (15)1.18395 (14)0.0234 (4)
H8BA0.74350.77701.24410.028*
H8BB0.85600.74401.13340.028*
C9A0.1884 (2)0.63848 (15)0.89249 (14)0.0244 (4)
C9B1.3076 (2)1.03973 (15)1.41662 (14)0.0225 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0243 (8)0.0220 (8)0.0230 (9)0.0012 (6)0.0011 (7)0.0094 (7)
O1A0.0311 (7)0.0361 (7)0.0429 (8)0.0016 (6)0.0072 (6)0.0051 (6)
C1B0.0197 (8)0.0223 (8)0.0233 (9)0.0008 (6)0.0016 (6)0.0103 (7)
O1B0.0224 (6)0.0298 (6)0.0228 (7)0.0001 (5)0.0050 (5)0.0082 (5)
C2A0.0259 (8)0.0196 (7)0.0238 (9)0.0028 (6)0.0005 (7)0.0078 (7)
O2A0.0360 (7)0.0332 (7)0.0260 (7)0.0020 (5)0.0001 (6)0.0032 (6)
C2B0.0192 (8)0.0238 (8)0.0221 (9)0.0001 (6)0.0012 (6)0.0091 (7)
O2B0.0181 (6)0.0393 (7)0.0229 (6)0.0033 (5)0.0001 (5)0.0131 (5)
C3A0.0309 (9)0.0283 (8)0.0230 (9)0.0039 (7)0.0035 (7)0.0117 (7)
O3A0.0268 (6)0.0342 (7)0.0287 (7)0.0068 (5)0.0007 (5)0.0003 (6)
C3B0.0209 (8)0.0246 (8)0.0272 (9)0.0042 (6)0.0019 (7)0.0127 (7)
O3B0.0223 (6)0.0522 (8)0.0236 (6)0.0044 (5)0.0002 (5)0.0204 (6)
C4AA0.0240 (8)0.0210 (8)0.0284 (9)0.0000 (6)0.0036 (7)0.0103 (7)
C4A0.0289 (9)0.0298 (9)0.0299 (10)0.0022 (7)0.0077 (7)0.0142 (8)
C4BA0.0196 (8)0.0211 (7)0.0207 (8)0.0015 (6)0.0003 (6)0.0091 (7)
C4B0.0247 (8)0.0220 (8)0.0270 (9)0.0001 (6)0.0006 (7)0.0137 (7)
C5A0.0256 (9)0.0274 (9)0.0409 (11)0.0037 (7)0.0049 (8)0.0129 (8)
C5B0.0252 (8)0.0227 (8)0.0233 (9)0.0010 (6)0.0034 (7)0.0116 (7)
C6A0.0288 (9)0.0198 (8)0.0367 (11)0.0074 (7)0.0026 (8)0.0046 (8)
C6B0.0177 (7)0.0252 (8)0.0245 (9)0.0048 (6)0.0011 (7)0.0089 (7)
C7A0.0328 (10)0.0338 (9)0.0303 (10)0.0087 (8)0.0004 (8)0.0040 (8)
C7B0.0228 (8)0.0271 (8)0.0249 (9)0.0058 (7)0.0024 (7)0.0099 (7)
C8AA0.0252 (8)0.0179 (7)0.0254 (9)0.0021 (6)0.0030 (7)0.0073 (7)
C8A0.0273 (9)0.0284 (8)0.0249 (9)0.0059 (7)0.0009 (7)0.0073 (7)
C8BA0.0207 (8)0.0214 (7)0.0209 (8)0.0042 (6)0.0040 (6)0.0103 (7)
C8B0.0244 (8)0.0253 (8)0.0225 (9)0.0012 (7)0.0006 (7)0.0116 (7)
C9A0.0275 (8)0.0243 (8)0.0229 (9)0.0051 (7)0.0024 (7)0.0111 (8)
C9B0.0231 (8)0.0203 (7)0.0222 (9)0.0030 (6)0.0014 (7)0.0065 (7)
Geometric parameters (Å, º) top
C1A—C8AA1.533 (2)C4AA—H4AA1.0000
C1A—C2A1.533 (2)C4A—H4A0.9900
C1A—H1A0.9900C4A—H4B0.9900
C1A—H1B0.9900C4BA—C4B1.523 (2)
O1A—C6A1.214 (2)C4BA—C8BA1.533 (2)
C1B—C8BA1.527 (2)C4BA—C5B1.535 (2)
C1B—C2B1.541 (2)C4BA—H4BC1.0000
C1B—H1BA0.9900C4B—H4BA0.9900
C1B—H1BB0.9900C4B—H4BB0.9900
O1B—C6B1.221 (2)C5A—C6A1.506 (3)
C2A—C9A1.515 (2)C5A—H5A0.9900
C2A—C3A1.526 (2)C5A—H5B0.9900
C2A—H2A1.0000C5B—C6B1.507 (2)
O2A—C9A1.211 (2)C5B—H5BA0.9900
C2B—C9B1.502 (2)C5B—H5BB0.9900
C2B—C3B1.527 (2)C6A—C7A1.506 (2)
C2B—H2BA1.0000C6B—C7B1.501 (2)
O2B—C9B1.2261 (19)C7A—C8A1.539 (2)
C3A—C4A1.518 (2)C7A—H7A0.9900
C3A—H3A0.9900C7A—H7B0.9900
C3A—H3B0.9900C7B—C8B1.542 (2)
O3A—C9A1.332 (2)C7B—H7BA0.9900
O3A—H3AA0.8400C7B—H7BB0.9900
C3B—C4B1.543 (2)C8AA—C8A1.523 (2)
C3B—H3BA0.9900C8AA—H8AA1.0000
C3B—H3BB0.9900C8A—H8A0.9900
O3B—C9B1.319 (2)C8A—H8B0.9900
O3B—H3BC0.8400C8BA—C8B1.524 (2)
C4AA—C4A1.523 (2)C8BA—H8BC1.0000
C4AA—C8AA1.528 (2)C8B—H8BA0.9900
C4AA—C5A1.533 (2)C8B—H8BB0.9900
C8AA—C1A—C2A112.20 (13)H4BA—C4B—H4BB107.9
C8AA—C1A—H1A109.2C6A—C5A—C4AA111.60 (14)
C2A—C1A—H1A109.2C6A—C5A—H5A109.3
C8AA—C1A—H1B109.2C4AA—C5A—H5A109.3
C2A—C1A—H1B109.2C6A—C5A—H5B109.3
H1A—C1A—H1B107.9C4AA—C5A—H5B109.3
C8BA—C1B—C2B111.04 (12)H5A—C5A—H5B108.0
C8BA—C1B—H1BA109.4C6B—C5B—C4BA111.60 (12)
C2B—C1B—H1BA109.4C6B—C5B—H5BA109.3
C8BA—C1B—H1BB109.4C4BA—C5B—H5BA109.3
C2B—C1B—H1BB109.4C6B—C5B—H5BB109.3
H1BA—C1B—H1BB108.0C4BA—C5B—H5BB109.3
C9A—C2A—C3A110.81 (13)H5BA—C5B—H5BB108.0
C9A—C2A—C1A113.07 (13)O1A—C6A—C5A122.44 (17)
C3A—C2A—C1A111.49 (13)O1A—C6A—C7A122.78 (18)
C9A—C2A—H2A107.0C5A—C6A—C7A114.78 (15)
C3A—C2A—H2A107.0O1B—C6B—C7B122.26 (15)
C1A—C2A—H2A107.0O1B—C6B—C5B121.72 (14)
C9B—C2B—C3B113.47 (13)C7B—C6B—C5B116.01 (14)
C9B—C2B—C1B106.93 (12)C6A—C7A—C8A111.43 (15)
C3B—C2B—C1B110.74 (13)C6A—C7A—H7A109.3
C9B—C2B—H2BA108.5C8A—C7A—H7A109.3
C3B—C2B—H2BA108.5C6A—C7A—H7B109.3
C1B—C2B—H2BA108.5C8A—C7A—H7B109.3
C4A—C3A—C2A112.41 (14)H7A—C7A—H7B108.0
C4A—C3A—H3A109.1C6B—C7B—C8B111.26 (13)
C2A—C3A—H3A109.1C6B—C7B—H7BA109.4
C4A—C3A—H3B109.1C8B—C7B—H7BA109.4
C2A—C3A—H3B109.1C6B—C7B—H7BB109.4
H3A—C3A—H3B107.9C8B—C7B—H7BB109.4
C9A—O3A—H3AA109.5H7BA—C7B—H7BB108.0
C2B—C3B—C4B109.73 (12)C8A—C8AA—C4AA111.35 (14)
C2B—C3B—H3BA109.7C8A—C8AA—C1A110.87 (13)
C4B—C3B—H3BA109.7C4AA—C8AA—C1A110.75 (13)
C2B—C3B—H3BB109.7C8A—C8AA—H8AA107.9
C4B—C3B—H3BB109.7C4AA—C8AA—H8AA107.9
H3BA—C3B—H3BB108.2C1A—C8AA—H8AA107.9
C9B—O3B—H3BC109.5C8AA—C8A—C7A112.95 (14)
C4A—C4AA—C8AA110.91 (14)C8AA—C8A—H8A109.0
C4A—C4AA—C5A111.68 (13)C7A—C8A—H8A109.0
C8AA—C4AA—C5A111.58 (14)C8AA—C8A—H8B109.0
C4A—C4AA—H4AA107.5C7A—C8A—H8B109.0
C8AA—C4AA—H4AA107.5H8A—C8A—H8B107.8
C5A—C4AA—H4AA107.5C8B—C8BA—C1B110.67 (12)
C3A—C4A—C4AA111.41 (13)C8B—C8BA—C4BA110.51 (13)
C3A—C4A—H4A109.3C1B—C8BA—C4BA110.87 (12)
C4AA—C4A—H4A109.3C8B—C8BA—H8BC108.2
C3A—C4A—H4B109.3C1B—C8BA—H8BC108.2
C4AA—C4A—H4B109.3C4BA—C8BA—H8BC108.2
H4A—C4A—H4B108.0C8BA—C8B—C7B112.52 (13)
C4B—C4BA—C8BA111.02 (13)C8BA—C8B—H8BA109.1
C4B—C4BA—C5B111.20 (12)C7B—C8B—H8BA109.1
C8BA—C4BA—C5B110.13 (12)C8BA—C8B—H8BB109.1
C4B—C4BA—H4BC108.1C7B—C8B—H8BB109.1
C8BA—C4BA—H4BC108.1H8BA—C8B—H8BB107.8
C5B—C4BA—H4BC108.1O2A—C9A—O3A122.41 (15)
C4BA—C4B—C3B111.95 (12)O2A—C9A—C2A124.21 (15)
C4BA—C4B—H4BA109.2O3A—C9A—C2A113.37 (14)
C3B—C4B—H4BA109.2O2B—C9B—O3B123.00 (15)
C4BA—C4B—H4BB109.2O2B—C9B—C2B123.74 (14)
C3B—C4B—H4BB109.2O3B—C9B—C2B113.15 (13)
C8AA—C1A—C2A—C9A177.89 (13)C4A—C4AA—C8AA—C8A179.66 (13)
C8AA—C1A—C2A—C3A52.26 (17)C5A—C4AA—C8AA—C8A54.47 (17)
C8BA—C1B—C2B—C9B178.25 (12)C4A—C4AA—C8AA—C1A56.49 (17)
C8BA—C1B—C2B—C3B57.67 (16)C5A—C4AA—C8AA—C1A178.32 (13)
C9A—C2A—C3A—C4A179.12 (13)C2A—C1A—C8AA—C8A178.72 (13)
C1A—C2A—C3A—C4A52.24 (17)C2A—C1A—C8AA—C4AA54.59 (17)
C9B—C2B—C3B—C4B177.08 (13)C4AA—C8AA—C8A—C7A53.32 (18)
C1B—C2B—C3B—C4B56.82 (16)C1A—C8AA—C8A—C7A177.10 (14)
C2A—C3A—C4A—C4AA54.78 (18)C6A—C7A—C8A—C8AA50.4 (2)
C8AA—C4AA—C4A—C3A56.74 (17)C2B—C1B—C8BA—C8B179.19 (12)
C5A—C4AA—C4A—C3A178.13 (13)C2B—C1B—C8BA—C4BA56.20 (17)
C8BA—C4BA—C4B—C3B55.67 (17)C4B—C4BA—C8BA—C8B178.23 (12)
C5B—C4BA—C4B—C3B178.66 (13)C5B—C4BA—C8BA—C8B58.16 (16)
C2B—C3B—C4B—C4BA56.48 (17)C4B—C4BA—C8BA—C1B55.15 (16)
C4A—C4AA—C5A—C6A178.16 (14)C5B—C4BA—C8BA—C1B178.76 (12)
C8AA—C4AA—C5A—C6A53.40 (18)C1B—C8BA—C8B—C7B179.76 (13)
C4B—C4BA—C5B—C6B177.98 (13)C4BA—C8BA—C8B—C7B56.56 (17)
C8BA—C4BA—C5B—C6B54.47 (17)C6B—C7B—C8B—C8BA50.10 (18)
C4AA—C5A—C6A—O1A127.84 (17)C3A—C2A—C9A—O2A9.3 (2)
C4AA—C5A—C6A—C7A52.11 (19)C1A—C2A—C9A—O2A135.34 (16)
C4BA—C5B—C6B—O1B128.63 (15)C3A—C2A—C9A—O3A170.88 (13)
C4BA—C5B—C6B—C7B50.60 (18)C1A—C2A—C9A—O3A44.88 (18)
O1A—C6A—C7A—C8A129.77 (18)C3B—C2B—C9B—O2B30.2 (2)
C5A—C6A—C7A—C8A50.2 (2)C1B—C2B—C9B—O2B92.18 (17)
O1B—C6B—C7B—C8B131.63 (15)C3B—C2B—C9B—O3B153.51 (14)
C5B—C6B—C7B—C8B47.59 (18)C1B—C2B—C9B—O3B84.10 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H3AA···O1B0.841.892.7219 (17)174
O3B—H3BC···O2Bi0.841.802.6368 (15)174
C3B—H3BB···O1Aii0.992.563.333 (2)135
C8A—H8B···O1Aiii0.992.563.521 (2)163
C4BA—H4BC···O2Aiv1.002.603.565 (2)161
C5B—H5BA···O1Bv0.992.573.201 (2)121
C1B—H1BB···O3Bvi0.992.603.303 (2)128
Symmetry codes: (i) x+3, y+2, z+3; (ii) x+2, y+1, z+1; (iii) x1, y+1, z+1; (iv) x+1, y, z; (v) x+1, y+2, z+2; (vi) x+2, y+2, z+3.
 

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