Download citation
Download citation
link to html
The title compound, C11H18O4, also known as piliformic acid, was isolated from the endophytic fungus Xylariasp sp. No. 2508 from mangrove trees from the coast of the South China Sea. The two carboxyl groups form inter­molecular O—H...O hydrogen bonds, which link the mol­ecules into infinite chains extending along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018253/cv2055sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018253/cv2055Isup2.hkl
Contains datablock I

CCDC reference: 610750

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.066
  • wR factor = 0.224
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.793 0.988 Tmin(prime) and Tmax expected: 0.973 0.987 RR(prime) = 0.814 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.29 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.54 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 25.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C3 - C5 ... 1.32 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Hexylidene-3-methylsuccinic acid top
Crystal data top
C11H18O4Z = 2
Mr = 214.25F(000) = 232
Triclinic, P1Dx = 1.109 Mg m3
a = 6.7208 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.488 (2) ÅCell parameters from 1921 reflections
c = 10.139 (2) Åθ = 2.0–26.0°
α = 85.994 (4)°µ = 0.08 mm1
β = 89.221 (4)°T = 294 K
γ = 84.457 (4)°Plate, colourless
V = 641.9 (2) Å30.32 × 0.24 × 0.16 mm
Data collection top
Bruker CCD area-detector
diffractometer
2497 independent reflections
Radiation source: fine-focus sealed tube1402 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.793, Tmax = 0.988k = 1111
5098 measured reflectionsl = 1212
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.224H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.114P)2 + 0.1365P]
where P = (Fo2 + 2Fc2)/3
2497 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.24 e Å3
178 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. The compound identity was conformed by the 1H NMR,13C NMR spectra and FAB mass spectrum. 1H NMR in DMSO-d6 (500 MHz): 12.03 (brs, 2H), 6.66 (t, 7.5 Hz, 1H), 3.52 (q, 7.0 Hz, 1H), 2.24–2.10 (m, 2H), 1.39 (dt, 7.0 Hz, 7.0 Hz, 2H), 1.34–1.20 (m, 4H), 1.18 (d, 7.0 Hz, 3H), 0.86 (t, 7.0 Hz, 3H). 13C NMR in DMSO-d6 (125 MHz): 174.3 (C), 167.3 (C), 142.2 (CH), 133.0 (C), 39.0 (CH2), 36.8 (C), 30.7 (CH2), 27.6 (CH2), 27.5 (CH2), 21.7 (CH2), 15.7 (CH3), 13.6 (CH3).

The FAB mass spectrum showed M + 1 ions at 215.

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*/UeqOcc. (<1)
O11.2879 (3)0.5941 (2)0.03452 (19)0.0730 (6)
O21.3895 (3)0.3756 (2)0.1144 (2)0.0793 (7)
H21.48590.38810.06610.119*
O31.3725 (4)0.5459 (3)0.3607 (2)0.0864 (8)
O41.3343 (4)0.3667 (3)0.5093 (2)0.0902 (8)
H41.43930.39010.53730.135*
C11.2646 (4)0.4893 (3)0.1072 (2)0.0596 (7)
C21.0787 (4)0.4776 (3)0.1911 (3)0.0691 (8)
H2A0.99280.42090.14340.083*
C31.1218 (4)0.3968 (4)0.3236 (3)0.0697 (8)
C41.2864 (5)0.4419 (4)0.4007 (3)0.0705 (8)
C51.0155 (5)0.2960 (4)0.3743 (3)0.0941 (11)
H51.05590.25400.45650.113*
C110.9598 (5)0.6218 (4)0.2037 (4)0.0962 (12)
H11A0.93680.66810.11730.144*
H11B1.03410.67930.25540.144*
H11C0.83400.60840.24630.144*
C60.8405 (7)0.2425 (5)0.3160 (5)0.1216 (14)0.520 (8)
H6A0.72750.31310.32450.146*0.520 (8)
H6B0.86670.23570.22220.146*0.520 (8)
C70.7809 (15)0.1057 (9)0.3700 (12)0.136 (3)0.520 (8)
H7A0.76940.10770.46530.163*0.520 (8)
H7B0.88600.03230.35120.163*0.520 (8)
C80.5906 (15)0.0667 (13)0.3183 (12)0.152 (3)0.520 (8)
H8A0.51630.02170.38940.182*0.520 (8)
H8B0.51060.15190.28460.182*0.520 (8)
C90.627 (2)0.0305 (15)0.2121 (15)0.174 (4)0.520 (8)
H9A0.73090.10410.24030.209*0.520 (8)
H9B0.67680.02180.13500.209*0.520 (8)
C100.449 (2)0.0995 (17)0.1726 (17)0.176 (5)0.520 (8)
H10A0.48900.16820.10980.265*0.520 (8)
H10B0.35180.02880.13320.265*0.520 (8)
H10C0.39210.14580.24920.265*0.520 (8)
C6'0.8405 (7)0.2425 (5)0.3160 (5)0.1216 (14)0.480 (8)
H6'A0.79180.30820.24330.146*0.480 (8)
H6'B0.73500.23910.38200.146*0.480 (8)
C7'0.8854 (18)0.0999 (10)0.2668 (14)0.150 (3)0.480 (8)
H7'A0.94130.03570.33840.180*0.480 (8)
H7'B0.98620.10480.19760.180*0.480 (8)
C8'0.7057 (19)0.0400 (16)0.2131 (14)0.167 (4)0.480 (8)
H8'A0.64030.11440.15380.200*0.480 (8)
H8'B0.75740.03520.15820.200*0.480 (8)
C9'0.544 (2)0.0186 (19)0.2967 (16)0.181 (4)0.480 (8)
H9'A0.49070.05610.35170.217*0.480 (8)
H9'B0.60760.09400.35560.217*0.480 (8)
C10'0.368 (3)0.076 (2)0.237 (2)0.196 (6)0.480 (8)
H10D0.27910.10550.30640.294*0.480 (8)
H10E0.41410.15630.18820.294*0.480 (8)
H10F0.29940.00400.17910.294*0.480 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0661 (13)0.0882 (14)0.0598 (12)0.0081 (10)0.0029 (9)0.0097 (11)
O20.0714 (14)0.0915 (15)0.0689 (13)0.0110 (12)0.0034 (10)0.0116 (11)
O30.0902 (16)0.1136 (18)0.0570 (12)0.0282 (14)0.0231 (11)0.0125 (12)
O40.0849 (16)0.132 (2)0.0529 (12)0.0208 (14)0.0236 (10)0.0179 (12)
C10.0534 (15)0.0829 (19)0.0405 (13)0.0033 (14)0.0146 (11)0.0009 (13)
C20.0511 (15)0.103 (2)0.0511 (15)0.0016 (15)0.0135 (12)0.0011 (14)
C30.0555 (16)0.102 (2)0.0505 (15)0.0066 (15)0.0073 (12)0.0024 (14)
C40.0634 (17)0.106 (2)0.0401 (13)0.0008 (16)0.0078 (12)0.0022 (14)
C50.075 (2)0.133 (3)0.072 (2)0.019 (2)0.0212 (17)0.023 (2)
C110.075 (2)0.133 (3)0.072 (2)0.024 (2)0.0024 (16)0.0102 (19)
C60.106 (3)0.142 (3)0.117 (3)0.035 (2)0.029 (2)0.022 (2)
C70.124 (5)0.141 (5)0.148 (5)0.047 (4)0.013 (4)0.003 (4)
C80.141 (5)0.153 (5)0.169 (6)0.048 (4)0.006 (5)0.018 (4)
C90.164 (6)0.176 (6)0.189 (6)0.041 (5)0.002 (5)0.034 (5)
C100.179 (8)0.172 (8)0.190 (9)0.056 (7)0.012 (7)0.045 (7)
C6'0.106 (3)0.142 (3)0.117 (3)0.035 (2)0.029 (2)0.022 (2)
C7'0.148 (5)0.156 (5)0.146 (5)0.008 (4)0.034 (5)0.009 (4)
C8'0.171 (6)0.161 (6)0.174 (6)0.027 (5)0.029 (5)0.021 (5)
C9'0.189 (6)0.181 (7)0.176 (7)0.028 (5)0.010 (5)0.030 (5)
C10'0.183 (9)0.201 (9)0.211 (10)0.046 (7)0.001 (8)0.023 (8)
Geometric parameters (Å, º) top
O1—C11.217 (3)C7—H7B0.9700
O2—C11.300 (3)C8—C91.469 (7)
O2—H20.8200C8—H8A0.9700
O3—C41.233 (4)C8—H8B0.9700
O4—C41.297 (3)C9—C101.488 (7)
O4—H40.8200C9—H9A0.9700
C1—C21.511 (4)C9—H9B0.9700
C2—C31.516 (4)C10—H10A0.9600
C2—C111.528 (5)C10—H10B0.9600
C2—H2A0.9800C10—H10C0.9600
C3—C51.320 (5)C7'—C8'1.507 (7)
C3—C41.476 (4)C7'—H7'A0.9700
C5—C61.472 (6)C7'—H7'B0.9700
C5—H50.9300C8'—C9'1.496 (7)
C11—H11A0.9600C8'—H8'A0.9700
C11—H11B0.9600C8'—H8'B0.9700
C11—H11C0.9600C9'—C10'1.498 (7)
C6—C71.464 (6)C9'—H9'A0.9700
C6—H6A0.9700C9'—H9'B0.9700
C6—H6B0.9700C10'—H10D0.9600
C7—C81.478 (7)C10'—H10E0.9600
C7—H7A0.9700C10'—H10F0.9600
C1—O2—H2109.5C9—C8—H8A109.4
C4—O4—H4109.5C7—C8—H8A109.4
O1—C1—O2123.7 (3)C9—C8—H8B109.4
O1—C1—C2122.1 (3)C7—C8—H8B109.4
O2—C1—C2114.1 (3)H8A—C8—H8B108.0
C1—C2—C3112.6 (2)C8—C9—C10115.0 (12)
C1—C2—C11112.1 (3)C8—C9—H9A108.5
C3—C2—C11113.0 (3)C10—C9—H9A108.5
C1—C2—H2A106.2C8—C9—H9B108.5
C3—C2—H2A106.2C10—C9—H9B108.5
C11—C2—H2A106.2H9A—C9—H9B107.5
C5—C3—C4119.7 (3)C9—C10—H10A109.5
C5—C3—C2123.9 (3)C9—C10—H10B109.5
C4—C3—C2116.3 (3)H10A—C10—H10B109.5
O3—C4—O4123.0 (3)C9—C10—H10C109.5
O3—C4—C3120.3 (2)H10A—C10—H10C109.5
O4—C4—C3116.8 (3)H10B—C10—H10C109.5
C3—C5—C6127.5 (3)C8'—C7'—H7'A108.8
C3—C5—H5116.3C8'—C7'—H7'B108.8
C6—C5—H5116.3H7'A—C7'—H7'B107.7
C2—C11—H11A109.5C9'—C8'—C7'124.4 (14)
C2—C11—H11B109.5C9'—C8'—H8'A106.2
H11A—C11—H11B109.5C7'—C8'—H8'A106.2
C2—C11—H11C109.5C9'—C8'—H8'B106.2
H11A—C11—H11C109.5C7'—C8'—H8'B106.2
H11B—C11—H11C109.5H8'A—C8'—H8'B106.4
C7—C6—C5117.7 (5)C8'—C9'—C10'121.9 (14)
C7—C6—H6A107.9C8'—C9'—H9'A106.8
C5—C6—H6A107.9C10'—C9'—H9'A106.8
C7—C6—H6B107.9C8'—C9'—H9'B106.8
C5—C6—H6B107.9C10'—C9'—H9'B106.8
H6A—C6—H6B107.2H9'A—C9'—H9'B106.7
C6—C7—C8114.8 (8)C9'—C10'—H10D109.5
C6—C7—H7A108.6C9'—C10'—H10E109.5
C8—C7—H7A108.6H10D—C10'—H10E109.5
C6—C7—H7B108.6C9'—C10'—H10F109.5
C8—C7—H7B108.6H10D—C10'—H10F109.5
H7A—C7—H7B107.5H10E—C10'—H10F109.5
C9—C8—C7111.0 (10)
O1—C1—C2—C3144.9 (3)C5—C3—C4—O48.4 (5)
O2—C1—C2—C338.7 (4)C2—C3—C4—O4175.0 (3)
O1—C1—C2—C1116.3 (4)C4—C3—C5—C6176.5 (4)
O2—C1—C2—C11167.4 (3)C2—C3—C5—C60.2 (7)
C1—C2—C3—C5133.6 (4)C3—C5—C6—C7163.1 (7)
C11—C2—C3—C598.2 (4)C5—C6—C7—C8172.9 (8)
C1—C2—C3—C449.9 (4)C6—C7—C8—C998.3 (14)
C11—C2—C3—C478.3 (3)C7—C8—C9—C10167.9 (12)
C5—C3—C4—O3172.1 (3)C7'—C8'—C9'—C10'179.8 (15)
C2—C3—C4—O34.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.832.652 (3)176
O4—H4···O3ii0.821.822.617 (3)164
Symmetry codes: (i) x+3, y+1, z; (ii) x+3, y+1, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds