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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004774/wn6088sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004774/wn6088Isup2.hkl
Contains datablock I

CCDC reference: 183808

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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.

(I) top
Crystal data top
C11H14O5·2(H2O)Z = 2
Mr = 262.25F(000) = 280.0
Triclinic, P1Dx = 1.285 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 6.556 (8) ÅCell parameters from 25 reflections
b = 10.02 (2) Åθ = 13.9–15.0°
c = 11.37 (2) ŵ = 0.11 mm1
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 scansh = 88
3296 measured reflectionsk = 013
3117 independent reflectionsl = 1414
1362 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.016 intensity decay: 0.2%
Refinement top
Refinement on F2H-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 = 0.93Δρmax = 0.21 e Å3
3117 reflectionsΔρmin = 0.28 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.4929 (3)0.8115 (2)0.8428 (2)0.0445 (5)
O20.2408 (4)0.6319 (2)0.7628 (2)0.0592 (7)
O30.2007 (3)1.2318 (2)0.7051 (2)0.0472 (6)
O40.2191 (3)1.1344 (2)0.5939 (2)0.0510 (6)
O50.3916 (3)0.8579 (2)0.5611 (2)0.0490 (6)
O60.4788 (3)0.6329 (2)0.4406 (2)0.0522 (6)
O70.0217 (3)0.4356 (2)0.6197 (2)0.0522 (6)
C10.1685 (4)0.8583 (3)0.7227 (3)0.0363 (6)
C20.2492 (4)1.0003 (3)0.7370 (3)0.0380 (7)
C30.1185 (4)1.0913 (3)0.6925 (3)0.0361 (7)
C40.0965 (4)1.0399 (3)0.6340 (3)0.0351 (6)
C50.1769 (4)0.8983 (3)0.6183 (3)0.0367 (7)
C60.0450 (5)0.8077 (3)0.6618 (3)0.0380 (7)
C70.3006 (5)0.7554 (3)0.7756 (3)0.0398 (7)
C80.6249 (5)0.7132 (3)0.9037 (3)0.0462 (8)
C90.8386 (5)0.7963 (3)0.9681 (3)0.0445 (7)
C100.9885 (6)0.7012 (4)1.0295 (3)0.0578 (9)
C111.2121 (6)0.7820 (5)1.0924 (4)0.075 (1)
H20.39241.03380.77700.0476*
H30.10271.27180.68150.0712*
H40.33821.09630.55550.0763*
H50.41540.78270.53650.0734*
H60.09770.71340.65030.0475*
H6A0.35800.62240.41940.0712*0.50
H6B0.49320.55060.47720.0507*0.50
H6C0.57730.67420.39610.0507*
H7A0.04960.48820.66440.0712*
H7B0.00850.47570.54510.0507*0.50
H7C0.15600.43280.60250.0507*0.50
H8A0.64950.66830.84370.0581*
H8B0.55010.63970.96290.0581*
H9A0.81270.83911.02940.0560*
H9B0.90880.87300.90880.0560*
H10A1.00810.65580.96800.0720*
H10B0.91880.62671.09010.0720*
H11A1.28350.85401.03250.0935*
H11B1.29930.71661.13010.0935*
H11C1.19370.82571.15440.0935*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.034 (1)0.036 (1)0.058 (1)0.0141 (9)0.0073 (10)0.0092 (10)
O20.051 (1)0.038 (1)0.081 (2)0.015 (1)0.016 (1)0.021 (1)
O30.035 (1)0.032 (1)0.069 (1)0.0082 (9)0.0029 (10)0.014 (1)
O40.037 (1)0.039 (1)0.072 (2)0.0162 (9)0.016 (1)0.021 (1)
O50.033 (1)0.042 (1)0.068 (2)0.0119 (9)0.0147 (10)0.022 (1)
O60.040 (1)0.043 (1)0.071 (2)0.0088 (9)0.007 (1)0.012 (1)
O70.047 (1)0.041 (1)0.062 (1)0.0080 (10)0.005 (1)0.017 (1)
C10.034 (1)0.035 (1)0.038 (2)0.010 (1)0.001 (1)0.006 (1)
C20.028 (1)0.038 (2)0.043 (2)0.007 (1)0.003 (1)0.008 (1)
C30.034 (1)0.030 (1)0.041 (2)0.005 (1)0.001 (1)0.010 (1)
C40.032 (1)0.035 (1)0.037 (2)0.013 (1)0.000 (1)0.006 (1)
C50.029 (1)0.036 (1)0.040 (2)0.006 (1)0.002 (1)0.010 (1)
C60.036 (1)0.033 (1)0.043 (2)0.007 (1)0.000 (1)0.011 (1)
C70.033 (1)0.039 (2)0.044 (2)0.009 (1)0.000 (1)0.010 (1)
C80.041 (2)0.037 (2)0.057 (2)0.019 (1)0.005 (1)0.004 (1)
C90.039 (2)0.047 (2)0.043 (2)0.014 (1)0.000 (1)0.006 (1)
C100.049 (2)0.065 (2)0.055 (2)0.027 (2)0.007 (2)0.004 (2)
C110.049 (2)0.109 (3)0.060 (2)0.032 (2)0.010 (2)0.008 (2)
Geometric parameters (Å, º) top
O1—C71.334 (3)C2—C31.371 (4)
O1—C81.455 (4)C2—H20.931
O2—C71.209 (4)C3—C41.395 (4)
O3—C31.370 (3)C4—C51.389 (4)
O3—H30.819C5—C61.373 (4)
O4—C41.358 (4)C6—H60.929
O4—H40.820C8—C91.500 (4)
O5—C51.375 (3)C8—H8A0.968
O5—H50.821C8—H8B0.970
O6—H6A0.750C9—C101.516 (5)
O6—H6B0.855C9—H9A0.971
O6—H6C0.860C9—H9B0.973
O7—H7A0.782C10—C111.528 (5)
O7—H7B0.862C10—H10A0.970
O7—H7C0.847C10—H10B0.971
C1—C21.388 (4)C11—H11A0.958
C1—C61.395 (4)C11—H11B0.961
C1—C71.479 (4)C11—H11C0.960
O1···O5i3.364 (7)O5···O5iv3.430 (4)
O1···C5i3.529 (4)O5···C2v3.585 (4)
O3···O7ii2.734 (3)O6···O6vii2.754 (4)
O3···O6iii2.806 (4)O6···O7viii2.803 (4)
O4···O5iv2.736 (4)O6···C3iii3.514 (4)
O4···O7ii2.944 (3)O6···C5i3.578 (4)
O4···O6v3.196 (4)O7···O7viii2.768 (4)
O4···C6v3.583 (4)C4···C6v3.572 (4)
O5···O6vi2.715 (3)C4···C5v3.582 (5)
O5···C7vi3.320 (4)
C7—O1—C8115.8 (2)O1—C7—O2122.6 (3)
C3—O3—H3109.6O1—C7—C1113.1 (3)
C4—O4—H4109.5O2—C7—C1124.3 (2)
C5—O5—H5109.5O1—C8—C9108.1 (2)
H6A—O6—H6B105.1O1—C8—H8A110.0
H6A—O6—H6C126.1O1—C8—H8B110.0
H6B—O6—H6C110.2C9—C8—H8A110.1
H7A—O7—H7B109.3C9—C8—H8B110.0
H7A—O7—H7C114.3H8A—C8—H8B108.6
H7B—O7—H7C90.1C8—C9—C10111.0 (3)
C2—C1—C6120.2 (3)C8—C9—H9A109.6
C2—C1—C7121.6 (2)C8—C9—H9B109.4
C6—C1—C7118.1 (3)C10—C9—H9A109.6
C1—C2—C3120.2 (2)C10—C9—H9B109.4
C1—C2—H2119.9H9A—C9—H9B107.8
C3—C2—H2119.9C9—C10—C11113.1 (3)
O3—C3—C2119.8 (2)C9—C10—H10A108.9
O3—C3—C4120.7 (3)C9—C10—H10B108.8
C2—C3—C4119.6 (3)C11—C10—H10A109.1
O4—C4—C3116.9 (2)C11—C10—H10B109.1
O4—C4—C5122.7 (2)H10A—C10—H10B107.7
C3—C4—C5120.4 (3)C10—C11—H11A109.5
O5—C5—C4115.8 (3)C10—C11—H11B109.4
O5—C5—C6124.2 (3)C10—C11—H11C109.4
C4—C5—C6119.9 (2)H11A—C11—H11B109.5
C1—C6—C5119.7 (3)H11A—C11—H11C109.6
C1—C6—H6120.2H11B—C11—H11C109.4
C5—C6—H6120.1
O1—C7—C1—C24.1 (4)O5—C5—C6—C1177.6 (3)
O1—C7—C1—C6173.2 (3)C1—C2—C3—C40.7 (5)
O1—C8—C9—C10177.7 (3)C1—C6—C5—C40.6 (5)
O2—C7—O1—C81.9 (5)C1—C7—O1—C8176.4 (3)
O2—C7—C1—C2177.7 (3)C2—C1—C6—C51.3 (5)
O2—C7—C1—C65.0 (5)C2—C3—C4—C51.4 (5)
O3—C3—C2—C1178.8 (3)C3—C2—C1—C60.7 (5)
O3—C3—C4—O41.6 (4)C3—C2—C1—C7176.5 (3)
O3—C3—C4—C5178.1 (3)C3—C4—C5—C60.8 (5)
O4—C4—C3—C2178.9 (3)C5—C6—C1—C7175.9 (3)
O4—C4—C5—O51.2 (4)C7—O1—C8—C9176.7 (3)
O4—C4—C5—C6179.6 (3)C8—C9—C10—C11177.8 (3)
O5—C5—C4—C3179.2 (3)C8—C9—C10—C11177.8 (3)
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x+1, y+2, z+1; (iv) x1, y+2, z+1; (v) x, y+2, z+1; (vi) x1, y, z; (vii) x+1, y+1, z+1; (viii) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.822.272.707 (5)114
O4—H4···O50.822.292.724 (5)113
O3—H3···O7ii0.821.972.734 (5)156
O4—H4···O5iv0.822.052.736 (4)142
O5—H5···O6vi0.821.922.715 (5)164
O6—H6A···O7viii0.752.062.803 (4)172
O6—H6B···O6vii0.861.902.755 (4)179
O6—H6C···O3iii0.861.952.803 (4)180
O7—H7A···O20.781.962.739 (3)174
O7—H7B···O7viii0.861.912.768 (5)180
O7—H7C···O6viii0.851.982.803 (4)163
Symmetry codes: (ii) x, y+1, z; (iii) x+1, y+2, z+1; (iv) x1, y+2, z+1; (vi) x1, y, z; (vii) x+1, y+1, z+1; (viii) x, y+1, z+1.
 

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