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The title compound, C10H12O4, also known as homovaretic acid, forms hydrogen bonds, which generate chains rather than dimers in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004902/cf6240sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004902/cf6240Isup2.hkl
Contains datablock I

CCDC reference: 209924

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.109
  • Data-to-parameter ratio = 12.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.73 From the CIF: _reflns_number_total 2193 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2349 Completeness (_total/calc) 93.36% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title compound, (I), can be used as the starting material for the synthesis of a large number of 1,2,3,4-tetrahydroisoquinoline compounds (Nagarajan et al., 1985). The molecules (Fig. 1) form O—H···O hydrogen bonds, resulting in an infinite chain along the crystallographic b axis (Figs. 2 and 3). It is noteworthy that 3-methoxyphenylacetic acid crystallizes in the same space group, but forms O—H···O hydrogen-bonded dimers (Choudhury & Guru Row, 2002). The torsion angles C4—C3—C2—C1 [−100.1 (1)°], C3—C2—C1—01 [86.2 (2)°] and C3—C2—C1—O2 [−90.8 (2)°] differ from those in 3-methoxyphenylacetic acid [88.1 (2), −0.2 (2) and 179.6 (1)°, respectively]. The two methoxy groups point away from each other [torsion angles C9—O3—C5— C6 = 175.6 (1)°, C10—O4—C6—C5 = 170.4 (1)° and O3—C5—C6—O4 = 1.3 (2)°]. The packing also involves two C—H···O hydrogen bonds (Table 2).

Experimental top

The 98% pure compound was purchased from Sigma Aldrich. Single crystals were grown from a mixture of ethyl acetate and hexane at 283 K by slow evaporation.

Refinement top

H atoms were located in a difference map and were refined isotropically. C—H distances are in the range 0.94 (2)–1.01 (2) Å and O—H is 0.95 (3) Å.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, shown with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed down the b axis.
[Figure 3] Fig. 3. The hydrogen-bonded chains in (I), viewed down the c axis.
3,4-dimethoxyphenyl acetic acid top
Crystal data top
C10H12O4F(000) = 416
Mr = 196.20Dx = 1.305 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 541 reflections
a = 14.258 (4) Åθ = 6.2–21.1°
b = 7.185 (2) ŵ = 0.10 mm1
c = 9.773 (3) ÅT = 293 K
β = 94.157 (5)°Prism, colourless
V = 998.5 (5) Å30.6 × 0.55 × 0.55 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2193 independent reflections
Radiation source: sealed tube1842 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ϕ and ω scansθmax = 27.7°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1817
Tmin = 0.942, Tmax = 0.947k = 99
7814 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0519P)2 + 0.196P]
where P = (Fo2 + 2Fc2)/3
2193 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C10H12O4V = 998.5 (5) Å3
Mr = 196.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.258 (4) ŵ = 0.10 mm1
b = 7.185 (2) ÅT = 293 K
c = 9.773 (3) Å0.6 × 0.55 × 0.55 mm
β = 94.157 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2193 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
1842 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.947Rint = 0.017
7814 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.109All H-atom parameters refined
S = 1.04Δρmax = 0.22 e Å3
2193 reflectionsΔρmin = 0.19 e Å3
175 parameters
Special details top

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
O40.05686 (6)0.08731 (13)0.37292 (10)0.0524 (3)
O30.19015 (7)0.15530 (13)0.38786 (10)0.0537 (3)
O20.42284 (9)0.52537 (16)0.11977 (13)0.0660 (3)
O10.49630 (8)0.31528 (15)0.25209 (14)0.0674 (3)
C50.20414 (9)0.00555 (17)0.30601 (13)0.0407 (3)
C60.13107 (8)0.12518 (18)0.29682 (13)0.0419 (3)
C40.28339 (9)0.02352 (19)0.23579 (13)0.0432 (3)
C30.29067 (9)0.17998 (18)0.15331 (13)0.0433 (3)
C80.21777 (10)0.3052 (2)0.14208 (14)0.0487 (3)
C70.13817 (10)0.2782 (2)0.21382 (15)0.0488 (3)
C20.37941 (11)0.2133 (2)0.07927 (17)0.0543 (4)
C10.43961 (9)0.35295 (19)0.15782 (16)0.0494 (3)
C90.25876 (14)0.2985 (2)0.3933 (2)0.0662 (5)
C100.01135 (12)0.2301 (3)0.3832 (2)0.0655 (5)
H40.3329 (11)0.063 (2)0.2420 (14)0.050 (4)*
H2B0.4142 (12)0.099 (2)0.0750 (16)0.059 (4)*
H80.2201 (11)0.416 (2)0.0855 (16)0.059 (4)*
H2A0.3630 (11)0.261 (2)0.0145 (18)0.067 (5)*
H70.0875 (11)0.365 (2)0.2051 (16)0.057 (4)*
H9A0.2648 (14)0.345 (3)0.298 (2)0.086 (6)*
H10C0.0545 (13)0.182 (3)0.4458 (19)0.072 (5)*
H10A0.0215 (13)0.344 (3)0.4186 (19)0.076 (5)*
H9B0.3205 (16)0.251 (3)0.438 (2)0.097 (7)*
H9C0.2338 (14)0.396 (3)0.450 (2)0.084 (6)*
H10B0.0419 (14)0.256 (3)0.297 (2)0.086 (6)*
H200.4596 (17)0.611 (3)0.174 (2)0.114 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0425 (5)0.0475 (6)0.0685 (6)0.0019 (4)0.0132 (4)0.0083 (5)
O30.0579 (6)0.0415 (5)0.0629 (6)0.0051 (4)0.0117 (5)0.0132 (4)
O20.0686 (7)0.0452 (6)0.0828 (8)0.0019 (5)0.0034 (6)0.0048 (5)
O10.0575 (6)0.0451 (6)0.0977 (9)0.0053 (5)0.0080 (6)0.0069 (6)
C50.0436 (6)0.0367 (6)0.0413 (6)0.0024 (5)0.0004 (5)0.0007 (5)
C60.0383 (6)0.0416 (7)0.0456 (7)0.0029 (5)0.0016 (5)0.0003 (5)
C40.0411 (6)0.0407 (7)0.0476 (7)0.0017 (5)0.0018 (5)0.0049 (5)
C30.0457 (7)0.0429 (7)0.0416 (7)0.0070 (5)0.0048 (5)0.0065 (5)
C80.0542 (8)0.0434 (7)0.0481 (7)0.0042 (6)0.0018 (6)0.0078 (6)
C70.0431 (7)0.0440 (7)0.0592 (8)0.0043 (6)0.0019 (6)0.0071 (6)
C20.0573 (8)0.0525 (9)0.0553 (9)0.0057 (7)0.0184 (7)0.0068 (7)
C10.0425 (7)0.0449 (7)0.0629 (8)0.0015 (6)0.0173 (6)0.0017 (6)
C90.0757 (11)0.0451 (8)0.0782 (12)0.0122 (8)0.0077 (9)0.0131 (8)
C100.0512 (9)0.0614 (10)0.0863 (13)0.0116 (8)0.0209 (9)0.0111 (9)
Geometric parameters (Å, º) top
O4—C61.3641 (15)C3—C21.5213 (19)
O4—C101.4223 (18)C8—C71.390 (2)
O3—C51.3640 (15)C8—H80.973 (17)
O3—C91.4182 (19)C7—H70.953 (16)
O2—C11.3104 (18)C2—C11.496 (2)
O2—H200.95 (3)C2—H2B0.962 (18)
O1—C11.2114 (18)C2—H2A0.989 (18)
C5—C41.3799 (18)C9—H9A1.00 (2)
C5—C61.4007 (18)C9—H9B1.01 (2)
C6—C71.3745 (19)C9—H9C0.97 (2)
C4—C31.3915 (19)C10—H10C0.961 (19)
C4—H40.941 (15)C10—H10A0.99 (2)
C3—C81.373 (2)C10—H10B0.94 (2)
C6—O4—C10117.13 (11)C1—C2—C3109.12 (12)
C5—O3—C9117.69 (12)C1—C2—H2B108.4 (10)
C1—O2—H20112.0 (15)C3—C2—H2B109.6 (10)
O3—C5—C4124.81 (12)C1—C2—H2A109.5 (10)
O3—C5—C6115.27 (11)C3—C2—H2A110.2 (10)
C4—C5—C6119.92 (12)H2B—C2—H2A109.9 (14)
O4—C6—C7125.07 (12)O1—C1—O2121.66 (14)
O4—C6—C5115.72 (11)O1—C1—C2124.55 (14)
C7—C6—C5119.21 (12)O2—C1—C2113.72 (14)
C5—C4—C3120.57 (12)O3—C9—H9A108.2 (12)
C5—C4—H4120.3 (9)O3—C9—H9B110.4 (13)
C3—C4—H4119.1 (9)H9A—C9—H9B112.3 (17)
C8—C3—C4119.20 (12)O3—C9—H9C105.3 (12)
C8—C3—C2120.63 (13)H9A—C9—H9C110.4 (16)
C4—C3—C2120.16 (13)H9B—C9—H9C110.0 (17)
C3—C8—C7120.61 (13)O4—C10—H10C105.0 (11)
C3—C8—H8121.7 (9)O4—C10—H10A108.0 (11)
C7—C8—H8117.7 (9)H10C—C10—H10A112.3 (15)
C6—C7—C8120.47 (13)O4—C10—H10B110.7 (13)
C6—C7—H7119.2 (9)H10C—C10—H10B111.4 (16)
C8—C7—H7120.3 (9)H10A—C10—H10B109.3 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H20···O1i0.94 (3)1.73 (3)2.651 (2)163 (3)
C4—H4···O1ii0.940 (15)2.583 (16)3.473 (2)158.2 (12)
C8—H8···O3iii0.977 (15)2.592 (15)3.537 (2)162.7 (13)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC10H12O4
Mr196.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.258 (4), 7.185 (2), 9.773 (3)
β (°) 94.157 (5)
V3)998.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.6 × 0.55 × 0.55
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.942, 0.947
No. of measured, independent and
observed [I > 2σ(I)] reflections
7814, 2193, 1842
Rint0.017
(sin θ/λ)max1)0.655
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.109, 1.04
No. of reflections2193
No. of parameters175
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.22, 0.19

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 1990).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H20···O1i0.94 (3)1.73 (3)2.651 (2)163 (3)
C4—H4···O1ii0.940 (15)2.583 (16)3.473 (2)158.2 (12)
C8—H8···O3iii0.977 (15)2.592 (15)3.537 (2)162.7 (13)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x, y+1/2, z1/2.
 

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