Buy article online - an online subscription or single-article purchase is required to access this article.
In the crystal structure of the title compound, 3,4,5-trihydroxybenzoic acid n-butyl ester dihydrate, C11H14O5·2H2O, the molecule is essentially in a planar conformation with a fully extended trans zigzag butyl ester group. There are two intramolecular hydrogen bonds between hydroxyl groups. The crystal structure is stabilized by the stacking interactions between gallate head groups, i.e. the 3,4,5-trihydroxybenzene part of butyl gallate, the hydrophobic interactions between alkyl groups, and all available intermolecular hydrogen bonds.
Supporting information
CCDC reference: 183808
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.048
- wR factor = 0.185
- Data-to-parameter ratio = 19.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.108
Value of mu given = 0.110
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and
Rigaku Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation and Rigaku Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
C11H14O5·2(H2O) | Z = 2 |
Mr = 262.25 | F(000) = 280.0 |
Triclinic, P1 | Dx = 1.285 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 6.556 (8) Å | Cell parameters from 25 reflections |
b = 10.02 (2) Å | θ = 13.9–15.0° |
c = 11.37 (2) Å | µ = 0.11 mm−1 |
α = 76.5 (1)° | T = 296 K |
β = 104.1 (1)° | Pillar, colorless |
γ = 108.2 (1)° | 0.50 × 0.20 × 0.10 mm |
V = 678 (2) Å3 | |
Data collection top
Rigaku AFC5R diffractometer | θmax = 27.5° |
ω–2θ scans | h = −8→8 |
3296 measured reflections | k = 0→13 |
3117 independent reflections | l = −14→14 |
1362 reflections with I > 2σ(I) | 3 standard reflections every 150 reflections |
Rint = 0.016 | intensity decay: 0.2% |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.185 | (Δ/σ)max = 0.001 |
S = 0.93 | Δρmax = 0.21 e Å−3 |
3117 reflections | Δρmin = −0.28 e Å−3 |
163 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.4929 (3) | 0.8115 (2) | 0.8428 (2) | 0.0445 (5) | |
O2 | 0.2408 (4) | 0.6319 (2) | 0.7628 (2) | 0.0592 (7) | |
O3 | 0.2007 (3) | 1.2318 (2) | 0.7051 (2) | 0.0472 (6) | |
O4 | −0.2191 (3) | 1.1344 (2) | 0.5939 (2) | 0.0510 (6) | |
O5 | −0.3916 (3) | 0.8579 (2) | 0.5611 (2) | 0.0490 (6) | |
O6 | 0.4788 (3) | 0.6329 (2) | 0.4406 (2) | 0.0522 (6) | |
O7 | −0.0217 (3) | 0.4356 (2) | 0.6197 (2) | 0.0522 (6) | |
C1 | 0.1685 (4) | 0.8583 (3) | 0.7227 (3) | 0.0363 (6) | |
C2 | 0.2492 (4) | 1.0003 (3) | 0.7370 (3) | 0.0380 (7) | |
C3 | 0.1185 (4) | 1.0913 (3) | 0.6925 (3) | 0.0361 (7) | |
C4 | −0.0965 (4) | 1.0399 (3) | 0.6340 (3) | 0.0351 (6) | |
C5 | −0.1769 (4) | 0.8983 (3) | 0.6183 (3) | 0.0367 (7) | |
C6 | −0.0450 (5) | 0.8077 (3) | 0.6618 (3) | 0.0380 (7) | |
C7 | 0.3006 (5) | 0.7554 (3) | 0.7756 (3) | 0.0398 (7) | |
C8 | 0.6249 (5) | 0.7132 (3) | 0.9037 (3) | 0.0462 (8) | |
C9 | 0.8386 (5) | 0.7963 (3) | 0.9681 (3) | 0.0445 (7) | |
C10 | 0.9885 (6) | 0.7012 (4) | 1.0295 (3) | 0.0578 (9) | |
C11 | 1.2121 (6) | 0.7820 (5) | 1.0924 (4) | 0.075 (1) | |
H2 | 0.3924 | 1.0338 | 0.7770 | 0.0476* | |
H3 | 0.1027 | 1.2718 | 0.6815 | 0.0712* | |
H4 | −0.3382 | 1.0963 | 0.5555 | 0.0763* | |
H5 | −0.4154 | 0.7827 | 0.5365 | 0.0734* | |
H6 | −0.0977 | 0.7134 | 0.6503 | 0.0475* | |
H6A | 0.3580 | 0.6224 | 0.4194 | 0.0712* | 0.50 |
H6B | 0.4932 | 0.5506 | 0.4772 | 0.0507* | 0.50 |
H6C | 0.5773 | 0.6742 | 0.3961 | 0.0507* | |
H7A | 0.0496 | 0.4882 | 0.6644 | 0.0712* | |
H7B | −0.0085 | 0.4757 | 0.5451 | 0.0507* | 0.50 |
H7C | −0.1560 | 0.4328 | 0.6025 | 0.0507* | 0.50 |
H8A | 0.6495 | 0.6683 | 0.8437 | 0.0581* | |
H8B | 0.5501 | 0.6397 | 0.9629 | 0.0581* | |
H9A | 0.8127 | 0.8391 | 1.0294 | 0.0560* | |
H9B | 0.9088 | 0.8730 | 0.9088 | 0.0560* | |
H10A | 1.0081 | 0.6558 | 0.9680 | 0.0720* | |
H10B | 0.9188 | 0.6267 | 1.0901 | 0.0720* | |
H11A | 1.2835 | 0.8540 | 1.0325 | 0.0935* | |
H11B | 1.2993 | 0.7166 | 1.1301 | 0.0935* | |
H11C | 1.1937 | 0.8257 | 1.1544 | 0.0935* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.034 (1) | 0.036 (1) | 0.058 (1) | 0.0141 (9) | −0.0073 (10) | −0.0092 (10) |
O2 | 0.051 (1) | 0.038 (1) | 0.081 (2) | 0.015 (1) | −0.016 (1) | −0.021 (1) |
O3 | 0.035 (1) | 0.032 (1) | 0.069 (1) | 0.0082 (9) | −0.0029 (10) | −0.014 (1) |
O4 | 0.037 (1) | 0.039 (1) | 0.072 (2) | 0.0162 (9) | −0.016 (1) | −0.021 (1) |
O5 | 0.033 (1) | 0.042 (1) | 0.068 (2) | 0.0119 (9) | −0.0147 (10) | −0.022 (1) |
O6 | 0.040 (1) | 0.043 (1) | 0.071 (2) | 0.0088 (9) | 0.007 (1) | −0.012 (1) |
O7 | 0.047 (1) | 0.041 (1) | 0.062 (1) | 0.0080 (10) | −0.005 (1) | −0.017 (1) |
C1 | 0.034 (1) | 0.035 (1) | 0.038 (2) | 0.010 (1) | 0.001 (1) | −0.006 (1) |
C2 | 0.028 (1) | 0.038 (2) | 0.043 (2) | 0.007 (1) | −0.003 (1) | −0.008 (1) |
C3 | 0.034 (1) | 0.030 (1) | 0.041 (2) | 0.005 (1) | 0.001 (1) | −0.010 (1) |
C4 | 0.032 (1) | 0.035 (1) | 0.037 (2) | 0.013 (1) | 0.000 (1) | −0.006 (1) |
C5 | 0.029 (1) | 0.036 (1) | 0.040 (2) | 0.006 (1) | −0.002 (1) | −0.010 (1) |
C6 | 0.036 (1) | 0.033 (1) | 0.043 (2) | 0.007 (1) | 0.000 (1) | −0.011 (1) |
C7 | 0.033 (1) | 0.039 (2) | 0.044 (2) | 0.009 (1) | 0.000 (1) | −0.010 (1) |
C8 | 0.041 (2) | 0.037 (2) | 0.057 (2) | 0.019 (1) | −0.005 (1) | −0.004 (1) |
C9 | 0.039 (2) | 0.047 (2) | 0.043 (2) | 0.014 (1) | 0.000 (1) | −0.006 (1) |
C10 | 0.049 (2) | 0.065 (2) | 0.055 (2) | 0.027 (2) | −0.007 (2) | −0.004 (2) |
C11 | 0.049 (2) | 0.109 (3) | 0.060 (2) | 0.032 (2) | −0.010 (2) | −0.008 (2) |
Geometric parameters (Å, º) top
O1—C7 | 1.334 (3) | C2—C3 | 1.371 (4) |
O1—C8 | 1.455 (4) | C2—H2 | 0.931 |
O2—C7 | 1.209 (4) | C3—C4 | 1.395 (4) |
O3—C3 | 1.370 (3) | C4—C5 | 1.389 (4) |
O3—H3 | 0.819 | C5—C6 | 1.373 (4) |
O4—C4 | 1.358 (4) | C6—H6 | 0.929 |
O4—H4 | 0.820 | C8—C9 | 1.500 (4) |
O5—C5 | 1.375 (3) | C8—H8A | 0.968 |
O5—H5 | 0.821 | C8—H8B | 0.970 |
O6—H6A | 0.750 | C9—C10 | 1.516 (5) |
O6—H6B | 0.855 | C9—H9A | 0.971 |
O6—H6C | 0.860 | C9—H9B | 0.973 |
O7—H7A | 0.782 | C10—C11 | 1.528 (5) |
O7—H7B | 0.862 | C10—H10A | 0.970 |
O7—H7C | 0.847 | C10—H10B | 0.971 |
C1—C2 | 1.388 (4) | C11—H11A | 0.958 |
C1—C6 | 1.395 (4) | C11—H11B | 0.961 |
C1—C7 | 1.479 (4) | C11—H11C | 0.960 |
| | | |
O1···O5i | 3.364 (7) | O5···O5iv | 3.430 (4) |
O1···C5i | 3.529 (4) | O5···C2v | 3.585 (4) |
O3···O7ii | 2.734 (3) | O6···O6vii | 2.754 (4) |
O3···O6iii | 2.806 (4) | O6···O7viii | 2.803 (4) |
O4···O5iv | 2.736 (4) | O6···C3iii | 3.514 (4) |
O4···O7ii | 2.944 (3) | O6···C5i | 3.578 (4) |
O4···O6v | 3.196 (4) | O7···O7viii | 2.768 (4) |
O4···C6v | 3.583 (4) | C4···C6v | 3.572 (4) |
O5···O6vi | 2.715 (3) | C4···C5v | 3.582 (5) |
O5···C7vi | 3.320 (4) | | |
| | | |
C7—O1—C8 | 115.8 (2) | O1—C7—O2 | 122.6 (3) |
C3—O3—H3 | 109.6 | O1—C7—C1 | 113.1 (3) |
C4—O4—H4 | 109.5 | O2—C7—C1 | 124.3 (2) |
C5—O5—H5 | 109.5 | O1—C8—C9 | 108.1 (2) |
H6A—O6—H6B | 105.1 | O1—C8—H8A | 110.0 |
H6A—O6—H6C | 126.1 | O1—C8—H8B | 110.0 |
H6B—O6—H6C | 110.2 | C9—C8—H8A | 110.1 |
H7A—O7—H7B | 109.3 | C9—C8—H8B | 110.0 |
H7A—O7—H7C | 114.3 | H8A—C8—H8B | 108.6 |
H7B—O7—H7C | 90.1 | C8—C9—C10 | 111.0 (3) |
C2—C1—C6 | 120.2 (3) | C8—C9—H9A | 109.6 |
C2—C1—C7 | 121.6 (2) | C8—C9—H9B | 109.4 |
C6—C1—C7 | 118.1 (3) | C10—C9—H9A | 109.6 |
C1—C2—C3 | 120.2 (2) | C10—C9—H9B | 109.4 |
C1—C2—H2 | 119.9 | H9A—C9—H9B | 107.8 |
C3—C2—H2 | 119.9 | C9—C10—C11 | 113.1 (3) |
O3—C3—C2 | 119.8 (2) | C9—C10—H10A | 108.9 |
O3—C3—C4 | 120.7 (3) | C9—C10—H10B | 108.8 |
C2—C3—C4 | 119.6 (3) | C11—C10—H10A | 109.1 |
O4—C4—C3 | 116.9 (2) | C11—C10—H10B | 109.1 |
O4—C4—C5 | 122.7 (2) | H10A—C10—H10B | 107.7 |
C3—C4—C5 | 120.4 (3) | C10—C11—H11A | 109.5 |
O5—C5—C4 | 115.8 (3) | C10—C11—H11B | 109.4 |
O5—C5—C6 | 124.2 (3) | C10—C11—H11C | 109.4 |
C4—C5—C6 | 119.9 (2) | H11A—C11—H11B | 109.5 |
C1—C6—C5 | 119.7 (3) | H11A—C11—H11C | 109.6 |
C1—C6—H6 | 120.2 | H11B—C11—H11C | 109.4 |
C5—C6—H6 | 120.1 | | |
| | | |
O1—C7—C1—C2 | 4.1 (4) | O5—C5—C6—C1 | −177.6 (3) |
O1—C7—C1—C6 | −173.2 (3) | C1—C2—C3—C4 | 0.7 (5) |
O1—C8—C9—C10 | −177.7 (3) | C1—C6—C5—C4 | 0.6 (5) |
O2—C7—O1—C8 | −1.9 (5) | C1—C7—O1—C8 | 176.4 (3) |
O2—C7—C1—C2 | −177.7 (3) | C2—C1—C6—C5 | −1.3 (5) |
O2—C7—C1—C6 | 5.0 (5) | C2—C3—C4—C5 | −1.4 (5) |
O3—C3—C2—C1 | −178.8 (3) | C3—C2—C1—C6 | 0.7 (5) |
O3—C3—C4—O4 | −1.6 (4) | C3—C2—C1—C7 | −176.5 (3) |
O3—C3—C4—C5 | 178.1 (3) | C3—C4—C5—C6 | 0.8 (5) |
O4—C4—C3—C2 | 178.9 (3) | C5—C6—C1—C7 | 175.9 (3) |
O4—C4—C5—O5 | −1.2 (4) | C7—O1—C8—C9 | 176.7 (3) |
O4—C4—C5—C6 | −179.6 (3) | C8—C9—C10—C11 | 177.8 (3) |
O5—C5—C4—C3 | 179.2 (3) | C8—C9—C10—C11 | 177.8 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) −x−1, −y+2, −z+1; (v) −x, −y+2, −z+1; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+1; (viii) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.82 | 2.27 | 2.707 (5) | 114 |
O4—H4···O5 | 0.82 | 2.29 | 2.724 (5) | 113 |
O3—H3···O7ii | 0.82 | 1.97 | 2.734 (5) | 156 |
O4—H4···O5iv | 0.82 | 2.05 | 2.736 (4) | 142 |
O5—H5···O6vi | 0.82 | 1.92 | 2.715 (5) | 164 |
O6—H6A···O7viii | 0.75 | 2.06 | 2.803 (4) | 172 |
O6—H6B···O6vii | 0.86 | 1.90 | 2.755 (4) | 179 |
O6—H6C···O3iii | 0.86 | 1.95 | 2.803 (4) | 180 |
O7—H7A···O2 | 0.78 | 1.96 | 2.739 (3) | 174 |
O7—H7B···O7viii | 0.86 | 1.91 | 2.768 (5) | 180 |
O7—H7C···O6viii | 0.85 | 1.98 | 2.803 (4) | 163 |
Symmetry codes: (ii) x, y+1, z; (iii) −x+1, −y+2, −z+1; (iv) −x−1, −y+2, −z+1; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+1; (viii) −x, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.