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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302926X/cf6318sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302926X/cf6318Isup2.hkl
Contains datablock I

CCDC reference: 234835

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.119
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT355_ALERT_3_A Long O-H Bond (0.82A) O2 - H2 = 1.24 Ang.
Author Response: Explained in the comment section.

Alert level C PLAT417_ALERT_2_C Short Inter D-H..H-D H2 .. H2 = 2.14 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

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
C12H14O4F(000) = 472
Mr = 222.23Dx = 1.279 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4888 reflections
a = 10.832 (4) Åθ = 2.9–27.5°
b = 8.845 (3) ŵ = 0.10 mm1
c = 12.922 (4) ÅT = 173 K
β = 111.22 (2)°Prism, colorless
V = 1154.1 (7) Å30.22 × 0.20 × 0.18 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1629 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 27.5°, θmin = 2.9°
ω and φ scansh = 1414
4888 measured reflectionsk = 1111
2619 independent reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H 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 reflectionsΔρmax = 0.14 e Å3
149 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.063 (16)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.42823 (11)0.17726 (12)0.96727 (8)0.0424 (3)
O20.36064 (11)0.04886 (11)0.88903 (8)0.0393 (3)
H20.4626 (16)0.1042 (18)0.9583 (12)0.047*
O30.20334 (12)0.03960 (14)0.57153 (9)0.0592 (4)
O40.37952 (10)0.08162 (12)0.69047 (8)0.0383 (3)
C10.22193 (14)0.16152 (16)0.81782 (11)0.0327 (4)
C20.17245 (15)0.12852 (17)0.70385 (11)0.0355 (4)
C30.04595 (16)0.17780 (18)0.63886 (13)0.0459 (5)
H30.01130.15490.56180.055*
C40.02973 (18)0.2597 (2)0.68516 (15)0.0534 (5)
H40.11650.29130.64030.064*
C50.02097 (18)0.2955 (2)0.79662 (16)0.0536 (5)
H50.03040.35340.82820.064*
C60.14623 (17)0.24755 (19)0.86238 (13)0.0444 (4)
H60.18090.27370.93890.053*
C70.34648 (15)0.09332 (17)0.89528 (11)0.0324 (4)
C80.25126 (16)0.04583 (17)0.64819 (11)0.0373 (4)
C90.46500 (17)0.0037 (2)0.64255 (13)0.0483 (5)
H9A0.43830.02880.56280.058*
H9B0.45770.10710.64970.058*
C100.60476 (17)0.05420 (19)0.70424 (13)0.0478 (5)
H10A0.60860.16570.69950.057*
H10B0.66240.01150.66710.057*
C110.65921 (17)0.0083 (2)0.82540 (14)0.0472 (4)
H11A0.60410.05490.86340.057*
H11B0.65190.10280.83040.057*
C120.80235 (18)0.0540 (2)0.88569 (16)0.0600 (5)
H12A0.83120.02060.96310.090*
H12B0.81020.16430.88330.090*
H12C0.85810.00680.84960.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0424 (7)0.0421 (6)0.0357 (6)0.0016 (5)0.0056 (5)0.0050 (5)
O20.0431 (7)0.0349 (6)0.0366 (6)0.0035 (5)0.0104 (5)0.0009 (4)
O30.0556 (8)0.0700 (9)0.0414 (7)0.0028 (6)0.0050 (6)0.0190 (6)
O40.0385 (7)0.0427 (6)0.0366 (6)0.0018 (5)0.0170 (5)0.0033 (5)
C10.0317 (9)0.0311 (8)0.0358 (8)0.0006 (6)0.0128 (6)0.0025 (6)
C20.0331 (9)0.0348 (8)0.0373 (8)0.0009 (7)0.0110 (7)0.0054 (6)
C30.0364 (10)0.0490 (10)0.0444 (9)0.0013 (8)0.0050 (7)0.0119 (8)
C40.0344 (10)0.0548 (11)0.0686 (12)0.0084 (8)0.0156 (9)0.0199 (9)
C50.0448 (11)0.0498 (10)0.0735 (13)0.0142 (8)0.0303 (10)0.0115 (9)
C60.0446 (11)0.0434 (9)0.0500 (9)0.0050 (8)0.0229 (8)0.0005 (8)
C70.0360 (9)0.0358 (8)0.0279 (7)0.0001 (7)0.0144 (6)0.0005 (7)
C80.0393 (10)0.0395 (9)0.0274 (7)0.0008 (7)0.0053 (7)0.0050 (7)
C90.0535 (12)0.0565 (11)0.0409 (9)0.0099 (9)0.0241 (8)0.0039 (8)
C100.0497 (11)0.0503 (10)0.0549 (10)0.0075 (8)0.0327 (9)0.0047 (8)
C110.0444 (11)0.0465 (10)0.0553 (10)0.0005 (8)0.0233 (8)0.0033 (8)
C120.0470 (12)0.0636 (12)0.0716 (12)0.0002 (9)0.0240 (10)0.0020 (10)
Geometric parameters (Å, º) top
O1—C71.267 (2)C5—C61.382 (2)
O2—C71.273 (2)C5—H50.950
O2—H21.24 (2)C6—H60.950
O3—C81.204 (2)C9—C101.501 (2)
O4—C81.334 (2)C9—H9A0.990
O4—C91.460 (2)C9—H9B0.990
C1—C61.387 (2)C10—C111.515 (2)
C1—C21.404 (2)C10—H10A0.990
C1—C71.486 (2)C10—H10B0.990
C2—C31.393 (2)C11—C121.517 (2)
C2—C81.492 (2)C11—H11A0.990
C3—C41.382 (2)C11—H11B0.990
C3—H30.950C12—H12A0.980
C4—C51.380 (3)C12—H12B0.980
C4—H40.950C12—H12C0.980
C7—O2—H2116.1 (7)O4—C8—C2112.27 (13)
C8—O4—C9116.14 (12)O4—C9—C10107.85 (13)
C6—C1—C2119.41 (14)O4—C9—H9A110.1
C6—C1—C7118.16 (13)C10—C9—H9A110.1
C2—C1—C7122.08 (13)O4—C9—H9B110.1
C3—C2—C1119.09 (15)C10—C9—H9B110.1
C3—C2—C8118.20 (14)H9A—C9—H9B108.4
C1—C2—C8122.69 (13)C9—C10—C11114.18 (14)
C4—C3—C2120.75 (15)C9—C10—H10A108.7
C4—C3—H3119.6C11—C10—H10A108.7
C2—C3—H3119.6C9—C10—H10B108.7
C5—C4—C3119.86 (16)C11—C10—H10B108.7
C5—C4—H4120.1H10A—C10—H10B107.6
C3—C4—H4120.1C12—C11—C10113.75 (15)
C6—C5—C4120.18 (17)C12—C11—H11A108.8
C6—C5—H5119.9C10—C11—H11A108.8
C4—C5—H5119.9C12—C11—H11B108.8
C5—C6—C1120.64 (15)C10—C11—H11B108.8
C5—C6—H6119.7H11A—C11—H11B107.7
C1—C6—H6119.7C11—C12—H12A109.5
O1—C7—O2123.88 (13)C11—C12—H12B109.5
O1—C7—C1118.66 (13)H12A—C12—H12B109.5
O2—C7—C1117.33 (13)C11—C12—H12C109.5
O3—C8—O4124.12 (15)H12A—C12—H12C109.5
O3—C8—C2123.57 (15)H12B—C12—H12C109.5
C6—C1—C2—C32.6 (2)C2—C1—C7—O1136.32 (15)
C7—C1—C2—C3170.44 (14)C6—C1—C7—O2125.46 (15)
C6—C1—C2—C8175.74 (14)C2—C1—C7—O247.7 (2)
C7—C1—C2—C811.2 (2)C9—O4—C8—O33.5 (2)
C1—C2—C3—C40.8 (2)C9—O4—C8—C2178.78 (12)
C8—C2—C3—C4177.65 (15)C3—C2—C8—O335.5 (2)
C2—C3—C4—C51.1 (3)C1—C2—C8—O3146.16 (16)
C3—C4—C5—C61.1 (3)C3—C2—C8—O4142.28 (14)
C4—C5—C6—C10.8 (3)C1—C2—C8—O436.1 (2)
C2—C1—C6—C52.6 (2)C8—O4—C9—C10177.58 (12)
C7—C1—C6—C5170.70 (15)O4—C9—C10—C1164.92 (18)
C6—C1—C7—O150.6 (2)C9—C10—C11—C12177.50 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i1.24 (2)1.39 (2)2.626 (2)175.4 (14)
Symmetry code: (i) x+1, y, z+2.
 

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