Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004902/cf6240sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004902/cf6240Isup2.hkl |
CCDC reference: 209924
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.
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.
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).
C10H12O4 | F(000) = 416 |
Mr = 196.20 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 541 reflections |
a = 14.258 (4) Å | θ = 6.2–21.1° |
b = 7.185 (2) Å | µ = 0.10 mm−1 |
c = 9.773 (3) Å | T = 293 K |
β = 94.157 (5)° | Prism, colourless |
V = 998.5 (5) Å3 | 0.6 × 0.55 × 0.55 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2193 independent reflections |
Radiation source: sealed tube | 1842 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ϕ and ω scans | θmax = 27.7°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −18→17 |
Tmin = 0.942, Tmax = 0.947 | k = −9→9 |
7814 measured reflections | l = −12→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | All 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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C10H12O4 | V = 998.5 (5) Å3 |
Mr = 196.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.258 (4) Å | µ = 0.10 mm−1 |
b = 7.185 (2) Å | T = 293 K |
c = 9.773 (3) Å | 0.6 × 0.55 × 0.55 mm |
β = 94.157 (5)° |
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 = 0.947 | Rint = 0.017 |
7814 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.109 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.22 e Å−3 |
2193 reflections | Δρmin = −0.19 e Å−3 |
175 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O4 | 0.05686 (6) | 0.08731 (13) | 0.37292 (10) | 0.0524 (3) | |
O3 | 0.19015 (7) | −0.15530 (13) | 0.38786 (10) | 0.0537 (3) | |
O2 | 0.42284 (9) | 0.52537 (16) | 0.11977 (13) | 0.0660 (3) | |
O1 | 0.49630 (8) | 0.31528 (15) | 0.25209 (14) | 0.0674 (3) | |
C5 | 0.20414 (9) | −0.00555 (17) | 0.30601 (13) | 0.0407 (3) | |
C6 | 0.13107 (8) | 0.12518 (18) | 0.29682 (13) | 0.0419 (3) | |
C4 | 0.28339 (9) | 0.02352 (19) | 0.23579 (13) | 0.0432 (3) | |
C3 | 0.29067 (9) | 0.17998 (18) | 0.15331 (13) | 0.0433 (3) | |
C8 | 0.21777 (10) | 0.3052 (2) | 0.14208 (14) | 0.0487 (3) | |
C7 | 0.13817 (10) | 0.2782 (2) | 0.21382 (15) | 0.0488 (3) | |
C2 | 0.37941 (11) | 0.2133 (2) | 0.07927 (17) | 0.0543 (4) | |
C1 | 0.43961 (9) | 0.35295 (19) | 0.15782 (16) | 0.0494 (3) | |
C9 | 0.25876 (14) | −0.2985 (2) | 0.3933 (2) | 0.0662 (5) | |
C10 | −0.01135 (12) | 0.2301 (3) | 0.3832 (2) | 0.0655 (5) | |
H4 | 0.3329 (11) | −0.063 (2) | 0.2420 (14) | 0.050 (4)* | |
H2B | 0.4142 (12) | 0.099 (2) | 0.0750 (16) | 0.059 (4)* | |
H8 | 0.2201 (11) | 0.416 (2) | 0.0855 (16) | 0.059 (4)* | |
H2A | 0.3630 (11) | 0.261 (2) | −0.0145 (18) | 0.067 (5)* | |
H7 | 0.0875 (11) | 0.365 (2) | 0.2051 (16) | 0.057 (4)* | |
H9A | 0.2648 (14) | −0.345 (3) | 0.298 (2) | 0.086 (6)* | |
H10C | −0.0545 (13) | 0.182 (3) | 0.4458 (19) | 0.072 (5)* | |
H10A | 0.0215 (13) | 0.344 (3) | 0.4186 (19) | 0.076 (5)* | |
H9B | 0.3205 (16) | −0.251 (3) | 0.438 (2) | 0.097 (7)* | |
H9C | 0.2338 (14) | −0.396 (3) | 0.450 (2) | 0.084 (6)* | |
H10B | −0.0419 (14) | 0.256 (3) | 0.297 (2) | 0.086 (6)* | |
H20 | 0.4596 (17) | 0.611 (3) | 0.174 (2) | 0.114 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0425 (5) | 0.0475 (6) | 0.0685 (6) | 0.0019 (4) | 0.0132 (4) | 0.0083 (5) |
O3 | 0.0579 (6) | 0.0415 (5) | 0.0629 (6) | 0.0051 (4) | 0.0117 (5) | 0.0132 (4) |
O2 | 0.0686 (7) | 0.0452 (6) | 0.0828 (8) | −0.0019 (5) | −0.0034 (6) | 0.0048 (5) |
O1 | 0.0575 (6) | 0.0451 (6) | 0.0977 (9) | −0.0053 (5) | −0.0080 (6) | 0.0069 (6) |
C5 | 0.0436 (6) | 0.0367 (6) | 0.0413 (6) | −0.0024 (5) | −0.0004 (5) | 0.0007 (5) |
C6 | 0.0383 (6) | 0.0416 (7) | 0.0456 (7) | −0.0029 (5) | 0.0016 (5) | −0.0003 (5) |
C4 | 0.0411 (6) | 0.0407 (7) | 0.0476 (7) | 0.0017 (5) | 0.0018 (5) | −0.0049 (5) |
C3 | 0.0457 (7) | 0.0429 (7) | 0.0416 (7) | −0.0070 (5) | 0.0048 (5) | −0.0065 (5) |
C8 | 0.0542 (8) | 0.0434 (7) | 0.0481 (7) | −0.0042 (6) | 0.0018 (6) | 0.0078 (6) |
C7 | 0.0431 (7) | 0.0440 (7) | 0.0592 (8) | 0.0043 (6) | 0.0019 (6) | 0.0071 (6) |
C2 | 0.0573 (8) | 0.0525 (9) | 0.0553 (9) | −0.0057 (7) | 0.0184 (7) | −0.0068 (7) |
C1 | 0.0425 (7) | 0.0449 (7) | 0.0629 (8) | −0.0015 (6) | 0.0173 (6) | 0.0017 (6) |
C9 | 0.0757 (11) | 0.0451 (8) | 0.0782 (12) | 0.0122 (8) | 0.0077 (9) | 0.0131 (8) |
C10 | 0.0512 (9) | 0.0614 (10) | 0.0863 (13) | 0.0116 (8) | 0.0209 (9) | 0.0111 (9) |
O4—C6 | 1.3641 (15) | C3—C2 | 1.5213 (19) |
O4—C10 | 1.4223 (18) | C8—C7 | 1.390 (2) |
O3—C5 | 1.3640 (15) | C8—H8 | 0.973 (17) |
O3—C9 | 1.4182 (19) | C7—H7 | 0.953 (16) |
O2—C1 | 1.3104 (18) | C2—C1 | 1.496 (2) |
O2—H20 | 0.95 (3) | C2—H2B | 0.962 (18) |
O1—C1 | 1.2114 (18) | C2—H2A | 0.989 (18) |
C5—C4 | 1.3799 (18) | C9—H9A | 1.00 (2) |
C5—C6 | 1.4007 (18) | C9—H9B | 1.01 (2) |
C6—C7 | 1.3745 (19) | C9—H9C | 0.97 (2) |
C4—C3 | 1.3915 (19) | C10—H10C | 0.961 (19) |
C4—H4 | 0.941 (15) | C10—H10A | 0.99 (2) |
C3—C8 | 1.373 (2) | C10—H10B | 0.94 (2) |
C6—O4—C10 | 117.13 (11) | C1—C2—C3 | 109.12 (12) |
C5—O3—C9 | 117.69 (12) | C1—C2—H2B | 108.4 (10) |
C1—O2—H20 | 112.0 (15) | C3—C2—H2B | 109.6 (10) |
O3—C5—C4 | 124.81 (12) | C1—C2—H2A | 109.5 (10) |
O3—C5—C6 | 115.27 (11) | C3—C2—H2A | 110.2 (10) |
C4—C5—C6 | 119.92 (12) | H2B—C2—H2A | 109.9 (14) |
O4—C6—C7 | 125.07 (12) | O1—C1—O2 | 121.66 (14) |
O4—C6—C5 | 115.72 (11) | O1—C1—C2 | 124.55 (14) |
C7—C6—C5 | 119.21 (12) | O2—C1—C2 | 113.72 (14) |
C5—C4—C3 | 120.57 (12) | O3—C9—H9A | 108.2 (12) |
C5—C4—H4 | 120.3 (9) | O3—C9—H9B | 110.4 (13) |
C3—C4—H4 | 119.1 (9) | H9A—C9—H9B | 112.3 (17) |
C8—C3—C4 | 119.20 (12) | O3—C9—H9C | 105.3 (12) |
C8—C3—C2 | 120.63 (13) | H9A—C9—H9C | 110.4 (16) |
C4—C3—C2 | 120.16 (13) | H9B—C9—H9C | 110.0 (17) |
C3—C8—C7 | 120.61 (13) | O4—C10—H10C | 105.0 (11) |
C3—C8—H8 | 121.7 (9) | O4—C10—H10A | 108.0 (11) |
C7—C8—H8 | 117.7 (9) | H10C—C10—H10A | 112.3 (15) |
C6—C7—C8 | 120.47 (13) | O4—C10—H10B | 110.7 (13) |
C6—C7—H7 | 119.2 (9) | H10C—C10—H10B | 111.4 (16) |
C8—C7—H7 | 120.3 (9) | H10A—C10—H10B | 109.3 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H20···O1i | 0.94 (3) | 1.73 (3) | 2.651 (2) | 163 (3) |
C4—H4···O1ii | 0.940 (15) | 2.583 (16) | 3.473 (2) | 158.2 (12) |
C8—H8···O3iii | 0.977 (15) | 2.592 (15) | 3.537 (2) | 162.7 (13) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H12O4 |
Mr | 196.20 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.258 (4), 7.185 (2), 9.773 (3) |
β (°) | 94.157 (5) |
V (Å3) | 998.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.6 × 0.55 × 0.55 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.942, 0.947 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7814, 2193, 1842 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.655 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.109, 1.04 |
No. of reflections | 2193 |
No. of parameters | 175 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H20···O1i | 0.94 (3) | 1.73 (3) | 2.651 (2) | 163 (3) |
C4—H4···O1ii | 0.940 (15) | 2.583 (16) | 3.473 (2) | 158.2 (12) |
C8—H8···O3iii | 0.977 (15) | 2.592 (15) | 3.537 (2) | 162.7 (13) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2. |
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).