organic compounds
The molecules of the title compound, C12H14O4, form dimeric pairs about inversion centers through hydrogen-bonding interactions between carboxylic acid groups. These hydrogen-bonding interactions can be described in terms of the graph-set notation R22(8).
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302926X/cf6318sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680302926X/cf6318Isup2.hkl |
CCDC reference: 234835
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Butylhydrogenphthalate top
Crystal data top
C12H14O4 | F(000) = 472 |
Mr = 222.23 | Dx = 1.279 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4888 reflections |
a = 10.832 (4) Å | θ = 2.9–27.5° |
b = 8.845 (3) Å | µ = 0.10 mm−1 |
c = 12.922 (4) Å | T = 173 K |
β = 111.22 (2)° | Prism, colorless |
V = 1154.1 (7) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 |
Data collection top
Nonius KappaCCD diffractometer | 1629 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 27.5°, θmin = 2.9° |
ω and φ scans | h = −14→14 |
4888 measured reflections | k = −11→11 |
2619 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.057P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.01 |
2619 reflections | Δρmax = 0.14 e Å−3 |
149 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.063 (16) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.42823 (11) | 0.17726 (12) | 0.96727 (8) | 0.0424 (3) | |
O2 | 0.36064 (11) | −0.04886 (11) | 0.88903 (8) | 0.0393 (3) | |
H2 | 0.4626 (16) | −0.1042 (18) | 0.9583 (12) | 0.047* | |
O3 | 0.20334 (12) | −0.03960 (14) | 0.57153 (9) | 0.0592 (4) | |
O4 | 0.37952 (10) | 0.08162 (12) | 0.69047 (8) | 0.0383 (3) | |
C1 | 0.22193 (14) | 0.16152 (16) | 0.81782 (11) | 0.0327 (4) | |
C2 | 0.17245 (15) | 0.12852 (17) | 0.70385 (11) | 0.0355 (4) | |
C3 | 0.04595 (16) | 0.17780 (18) | 0.63886 (13) | 0.0459 (5) | |
H3 | 0.0113 | 0.1549 | 0.5618 | 0.055* | |
C4 | −0.02973 (18) | 0.2597 (2) | 0.68516 (15) | 0.0534 (5) | |
H4 | −0.1165 | 0.2913 | 0.6403 | 0.064* | |
C5 | 0.02097 (18) | 0.2955 (2) | 0.79662 (16) | 0.0536 (5) | |
H5 | −0.0304 | 0.3534 | 0.8282 | 0.064* | |
C6 | 0.14623 (17) | 0.24755 (19) | 0.86238 (13) | 0.0444 (4) | |
H6 | 0.1809 | 0.2737 | 0.9389 | 0.053* | |
C7 | 0.34648 (15) | 0.09332 (17) | 0.89528 (11) | 0.0324 (4) | |
C8 | 0.25126 (16) | 0.04583 (17) | 0.64819 (11) | 0.0373 (4) | |
C9 | 0.46500 (17) | 0.0037 (2) | 0.64255 (13) | 0.0483 (5) | |
H9A | 0.4383 | 0.0288 | 0.5628 | 0.058* | |
H9B | 0.4577 | −0.1071 | 0.6497 | 0.058* | |
C10 | 0.60476 (17) | 0.05420 (19) | 0.70424 (13) | 0.0478 (5) | |
H10A | 0.6086 | 0.1657 | 0.6995 | 0.057* | |
H10B | 0.6624 | 0.0115 | 0.6671 | 0.057* | |
C11 | 0.65921 (17) | 0.0083 (2) | 0.82540 (14) | 0.0472 (4) | |
H11A | 0.6041 | 0.0549 | 0.8634 | 0.057* | |
H11B | 0.6519 | −0.1028 | 0.8304 | 0.057* | |
C12 | 0.80235 (18) | 0.0540 (2) | 0.88569 (16) | 0.0600 (5) | |
H12A | 0.8312 | 0.0206 | 0.9631 | 0.090* | |
H12B | 0.8102 | 0.1643 | 0.8833 | 0.090* | |
H12C | 0.8581 | 0.0068 | 0.8496 | 0.090* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0424 (7) | 0.0421 (6) | 0.0357 (6) | −0.0016 (5) | 0.0056 (5) | −0.0050 (5) |
O2 | 0.0431 (7) | 0.0349 (6) | 0.0366 (6) | 0.0035 (5) | 0.0104 (5) | 0.0009 (4) |
O3 | 0.0556 (8) | 0.0700 (9) | 0.0414 (7) | −0.0028 (6) | 0.0050 (6) | −0.0190 (6) |
O4 | 0.0385 (7) | 0.0427 (6) | 0.0366 (6) | 0.0018 (5) | 0.0170 (5) | −0.0033 (5) |
C1 | 0.0317 (9) | 0.0311 (8) | 0.0358 (8) | −0.0006 (6) | 0.0128 (6) | 0.0025 (6) |
C2 | 0.0331 (9) | 0.0348 (8) | 0.0373 (8) | −0.0009 (7) | 0.0110 (7) | 0.0054 (6) |
C3 | 0.0364 (10) | 0.0490 (10) | 0.0444 (9) | −0.0013 (8) | 0.0050 (7) | 0.0119 (8) |
C4 | 0.0344 (10) | 0.0548 (11) | 0.0686 (12) | 0.0084 (8) | 0.0156 (9) | 0.0199 (9) |
C5 | 0.0448 (11) | 0.0498 (10) | 0.0735 (13) | 0.0142 (8) | 0.0303 (10) | 0.0115 (9) |
C6 | 0.0446 (11) | 0.0434 (9) | 0.0500 (9) | 0.0050 (8) | 0.0229 (8) | 0.0005 (8) |
C7 | 0.0360 (9) | 0.0358 (8) | 0.0279 (7) | −0.0001 (7) | 0.0144 (6) | 0.0005 (7) |
C8 | 0.0393 (10) | 0.0395 (9) | 0.0274 (7) | 0.0008 (7) | 0.0053 (7) | 0.0050 (7) |
C9 | 0.0535 (12) | 0.0565 (11) | 0.0409 (9) | 0.0099 (9) | 0.0241 (8) | −0.0039 (8) |
C10 | 0.0497 (11) | 0.0503 (10) | 0.0549 (10) | 0.0075 (8) | 0.0327 (9) | 0.0047 (8) |
C11 | 0.0444 (11) | 0.0465 (10) | 0.0553 (10) | 0.0005 (8) | 0.0233 (8) | 0.0033 (8) |
C12 | 0.0470 (12) | 0.0636 (12) | 0.0716 (12) | −0.0002 (9) | 0.0240 (10) | −0.0020 (10) |
Geometric parameters (Å, º) top
O1—C7 | 1.267 (2) | C5—C6 | 1.382 (2) |
O2—C7 | 1.273 (2) | C5—H5 | 0.950 |
O2—H2 | 1.24 (2) | C6—H6 | 0.950 |
O3—C8 | 1.204 (2) | C9—C10 | 1.501 (2) |
O4—C8 | 1.334 (2) | C9—H9A | 0.990 |
O4—C9 | 1.460 (2) | C9—H9B | 0.990 |
C1—C6 | 1.387 (2) | C10—C11 | 1.515 (2) |
C1—C2 | 1.404 (2) | C10—H10A | 0.990 |
C1—C7 | 1.486 (2) | C10—H10B | 0.990 |
C2—C3 | 1.393 (2) | C11—C12 | 1.517 (2) |
C2—C8 | 1.492 (2) | C11—H11A | 0.990 |
C3—C4 | 1.382 (2) | C11—H11B | 0.990 |
C3—H3 | 0.950 | C12—H12A | 0.980 |
C4—C5 | 1.380 (3) | C12—H12B | 0.980 |
C4—H4 | 0.950 | C12—H12C | 0.980 |
C7—O2—H2 | 116.1 (7) | O4—C8—C2 | 112.27 (13) |
C8—O4—C9 | 116.14 (12) | O4—C9—C10 | 107.85 (13) |
C6—C1—C2 | 119.41 (14) | O4—C9—H9A | 110.1 |
C6—C1—C7 | 118.16 (13) | C10—C9—H9A | 110.1 |
C2—C1—C7 | 122.08 (13) | O4—C9—H9B | 110.1 |
C3—C2—C1 | 119.09 (15) | C10—C9—H9B | 110.1 |
C3—C2—C8 | 118.20 (14) | H9A—C9—H9B | 108.4 |
C1—C2—C8 | 122.69 (13) | C9—C10—C11 | 114.18 (14) |
C4—C3—C2 | 120.75 (15) | C9—C10—H10A | 108.7 |
C4—C3—H3 | 119.6 | C11—C10—H10A | 108.7 |
C2—C3—H3 | 119.6 | C9—C10—H10B | 108.7 |
C5—C4—C3 | 119.86 (16) | C11—C10—H10B | 108.7 |
C5—C4—H4 | 120.1 | H10A—C10—H10B | 107.6 |
C3—C4—H4 | 120.1 | C12—C11—C10 | 113.75 (15) |
C6—C5—C4 | 120.18 (17) | C12—C11—H11A | 108.8 |
C6—C5—H5 | 119.9 | C10—C11—H11A | 108.8 |
C4—C5—H5 | 119.9 | C12—C11—H11B | 108.8 |
C5—C6—C1 | 120.64 (15) | C10—C11—H11B | 108.8 |
C5—C6—H6 | 119.7 | H11A—C11—H11B | 107.7 |
C1—C6—H6 | 119.7 | C11—C12—H12A | 109.5 |
O1—C7—O2 | 123.88 (13) | C11—C12—H12B | 109.5 |
O1—C7—C1 | 118.66 (13) | H12A—C12—H12B | 109.5 |
O2—C7—C1 | 117.33 (13) | C11—C12—H12C | 109.5 |
O3—C8—O4 | 124.12 (15) | H12A—C12—H12C | 109.5 |
O3—C8—C2 | 123.57 (15) | H12B—C12—H12C | 109.5 |
C6—C1—C2—C3 | −2.6 (2) | C2—C1—C7—O1 | 136.32 (15) |
C7—C1—C2—C3 | 170.44 (14) | C6—C1—C7—O2 | 125.46 (15) |
C6—C1—C2—C8 | 175.74 (14) | C2—C1—C7—O2 | −47.7 (2) |
C7—C1—C2—C8 | −11.2 (2) | C9—O4—C8—O3 | −3.5 (2) |
C1—C2—C3—C4 | 0.8 (2) | C9—O4—C8—C2 | 178.78 (12) |
C8—C2—C3—C4 | −177.65 (15) | C3—C2—C8—O3 | −35.5 (2) |
C2—C3—C4—C5 | 1.1 (3) | C1—C2—C8—O3 | 146.16 (16) |
C3—C4—C5—C6 | −1.1 (3) | C3—C2—C8—O4 | 142.28 (14) |
C4—C5—C6—C1 | −0.8 (3) | C1—C2—C8—O4 | −36.1 (2) |
C2—C1—C6—C5 | 2.6 (2) | C8—O4—C9—C10 | −177.58 (12) |
C7—C1—C6—C5 | −170.70 (15) | O4—C9—C10—C11 | 64.92 (18) |
C6—C1—C7—O1 | −50.6 (2) | C9—C10—C11—C12 | 177.50 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 1.24 (2) | 1.39 (2) | 2.626 (2) | 175.4 (14) |
Symmetry code: (i) −x+1, −y, −z+2. |