supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2010). E66, o485    [ doi:10.1107/S1600536810000139 ]

Propyl 4-hydroxybenzoate

Y. Zhou, G. Matsadiq, Y. Wu, J. Xiao and J. Cheng

Abstract top

There are two molecules in the asymmetric unit of the title compound, C10H12O3. In the crystal, molecules are linked by O-H...O hydrogen bonds into chains running along [010]. Adjacent chains are joined together by weak [pi]-[pi] interactions between benzene rings [centroid-centroid distance = 4.040 (2) Å].

Comment top

The propyl 4-hydroxybenzoate is a kind of p-hydroxybenzoates, which are also known as Nipagin esters. Nipagin ester is a preservative of large consumption in the world. Due to the high antibacterial activity and low toxicity of Nipagin ester, it becomes an inevitable trend that Nipagin ester replaces the traditional preservative. Here, we report the crystal structure of propyl 4-hydroxybenzoate.

There are two molecules in the asymmetric unit (Fig. 1). All bond lengths and bond angles lie in expected ranges.

As shown in Fig.2, molecules are linked by O—H···O hydrogen bonds into one-dimensional chains running along the [010] direction. Adjacent chains are further linked together by weak π–π interactions between two phenyl rings (centroid-to-centroid distance is 4.040 Å).

Related literature top

For related literature [on what subject?], see: Mandal & Kadirvelraj (1996).

Experimental top

1H-NMR (C3D6O,600MHZ):δ7.916(d,2H,aromatic),δ6.933(d,2H,aromatic), δ4.208(t,2H,-COOCH2-),δ2.096(s,1H,-OH),δ1.752(q,2H,-CH2-), δ1.004(t,3H,-CH3);

Crystals appropriate for data collection were obtained by slow evaporation of an ethanol solution at room temperature.

Refinement top

All the H atoms attached to carbon atoms were located from geometrical considerations with C—H= 0.93Å (aromatic), 0.97Å (methylene) and 0.96Å (methyl), and Ueq(H)=1.2Ueq(aromatic, methylene C) and 1.5Ueq(methyl C). Hydrogen atoms H1 and H4 were found from difference maps and then placed at their ideal positions with O—H=0.82Å and Uiso(H)=1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing of (I), with O-H···O hydrogen bonds shown as dashed lines.
Propyl 4-hydroxybenzoate top
Crystal data top
C10H12O3F(000) = 768
Mr = 180.20Dx = 1.282 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4791 reflections
a = 12.0634 (12) Åθ = 2.3–28.3°
b = 13.8419 (14) ŵ = 0.09 mm−1
c = 11.7982 (11) ÅT = 298 K
β = 108.625 (2)°Block, colourless
V = 1866.9 (3) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2960 reflections with I > 2σ(I)
Radiation source: fine focus sealed Siemens Mo tubeRint = 0.027
graphiteθmax = 25.0°, θmin = 2.3°
0.3° wide ω exposures scansh = −14→12
10603 measured reflectionsk = −16→16
3271 independent reflectionsl = −11→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.083Hydrogen site location: geom and difmap
wR(F2) = 0.189H-atom parameters constrained
S = 1.27 w = 1/[σ2(Fo2) + (0.0626P)2 + 1.2781P]
where P = (Fo2 + 2Fc2)/3
3271 reflections(Δ/σ)max = 0.001
237 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C10H12O3V = 1866.9 (3) Å3
Mr = 180.20Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.0634 (12) ŵ = 0.09 mm−1
b = 13.8419 (14) ÅT = 298 K
c = 11.7982 (11) Å0.30 × 0.20 × 0.20 mm
β = 108.625 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2960 reflections with I > 2σ(I)
10603 measured reflectionsRint = 0.027
3271 independent reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.083H-atom parameters constrained
wR(F2) = 0.189Δρmax = 0.24 e Å−3
S = 1.27Δρmin = −0.29 e Å−3
3271 reflectionsAbsolute structure: ?
237 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.9740 (2)0.97287 (14)0.3245 (2)0.0657 (7)
H11.00930.97970.27600.098*
O20.9063 (2)0.51536 (14)0.3293 (2)0.0608 (6)
O30.82019 (18)0.56944 (13)0.45749 (18)0.0488 (5)
C10.9519 (3)0.87795 (19)0.3346 (3)0.0447 (7)
C20.8980 (3)0.8521 (2)0.4176 (3)0.0545 (8)
H20.87770.89960.46310.065*
C30.8744 (3)0.75689 (19)0.4330 (3)0.0461 (7)
H30.83810.74030.48900.055*
C40.9044 (2)0.68486 (19)0.3652 (2)0.0370 (6)
C50.9577 (3)0.7118 (2)0.2820 (3)0.0460 (7)
H50.97810.66460.23620.055*
C60.9810 (3)0.8072 (2)0.2660 (3)0.0467 (7)
H61.01620.82420.20930.056*
C70.8785 (2)0.5822 (2)0.3806 (3)0.0403 (7)
C80.7870 (3)0.4715 (2)0.4759 (3)0.0527 (8)
H8A0.85600.43350.51560.063*
H8B0.74630.44140.39970.063*
C90.7087 (4)0.4766 (2)0.5519 (3)0.0672 (10)
H9A0.75090.50670.62770.081*
H9B0.64180.51700.51240.081*
C100.6668 (4)0.3798 (3)0.5749 (4)0.0862 (13)
H10A0.62030.35160.50060.129*
H10B0.62020.38640.62700.129*
H10C0.73270.33890.61200.129*
O40.5717 (2)0.61479 (15)0.7201 (2)0.0742 (8)
H40.52980.60820.76220.111*
O50.5895 (2)1.07375 (15)0.6687 (2)0.0594 (6)
O60.68661 (18)1.01843 (13)0.55031 (18)0.0492 (5)
C110.5838 (3)0.7104 (2)0.7005 (3)0.0482 (7)
C120.6369 (3)0.7352 (2)0.6165 (3)0.0610 (9)
H120.66330.68710.57660.073*
C130.6507 (3)0.8303 (2)0.5919 (3)0.0497 (8)
H130.68600.84620.53490.060*
C140.6125 (2)0.9033 (2)0.6512 (2)0.0385 (6)
C150.5595 (3)0.8775 (2)0.7353 (3)0.0441 (7)
H150.53350.92560.77570.053*
C160.5447 (3)0.7818 (2)0.7602 (3)0.0470 (7)
H160.50880.76560.81660.056*
C170.6265 (2)1.0062 (2)0.6259 (2)0.0403 (7)
C180.7092 (3)1.11661 (19)0.5211 (3)0.0476 (7)
H18A0.75971.14910.59160.057*
H18B0.63651.15240.49180.057*
C190.7673 (3)1.1111 (2)0.4270 (3)0.0526 (8)
H19A0.71621.07760.35770.063*
H19B0.83901.07410.45710.063*
C200.7954 (3)1.2110 (2)0.3895 (3)0.0672 (10)
H20A0.72431.24700.35710.101*
H20B0.83371.20470.33000.101*
H20C0.84611.24430.45790.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1019 (19)0.0285 (11)0.0922 (17)−0.0029 (11)0.0670 (15)0.0030 (11)
O20.0824 (16)0.0342 (11)0.0856 (16)−0.0030 (10)0.0544 (14)−0.0113 (11)
O30.0671 (14)0.0298 (10)0.0629 (13)−0.0052 (9)0.0393 (11)−0.0006 (9)
C10.0551 (18)0.0306 (14)0.0554 (18)−0.0010 (12)0.0275 (15)0.0017 (12)
C20.078 (2)0.0349 (15)0.069 (2)0.0015 (15)0.0485 (18)−0.0054 (14)
C30.0614 (19)0.0340 (15)0.0558 (18)−0.0001 (13)0.0370 (16)0.0031 (12)
C40.0394 (15)0.0325 (14)0.0419 (15)−0.0006 (11)0.0168 (12)−0.0009 (11)
C50.0575 (18)0.0392 (15)0.0520 (17)−0.0024 (13)0.0325 (15)−0.0083 (13)
C60.0606 (19)0.0425 (16)0.0486 (17)−0.0022 (14)0.0337 (15)0.0032 (13)
C70.0398 (15)0.0372 (15)0.0479 (16)0.0008 (12)0.0198 (13)−0.0033 (12)
C80.068 (2)0.0302 (15)0.066 (2)−0.0044 (14)0.0305 (17)0.0049 (13)
C90.101 (3)0.0448 (18)0.072 (2)−0.0123 (18)0.051 (2)−0.0045 (16)
C100.121 (4)0.063 (2)0.099 (3)−0.018 (2)0.070 (3)0.000 (2)
O40.107 (2)0.0348 (12)0.111 (2)−0.0041 (12)0.0776 (17)0.0060 (12)
O50.0821 (16)0.0367 (12)0.0756 (15)0.0051 (10)0.0478 (13)−0.0039 (10)
O60.0660 (13)0.0292 (10)0.0655 (13)−0.0020 (9)0.0395 (11)−0.0008 (9)
C110.0502 (17)0.0375 (15)0.0637 (19)−0.0021 (13)0.0279 (15)0.0039 (14)
C120.079 (2)0.0347 (16)0.093 (3)0.0007 (15)0.061 (2)−0.0071 (16)
C130.0618 (19)0.0394 (16)0.065 (2)−0.0035 (14)0.0435 (17)−0.0034 (14)
C140.0347 (14)0.0397 (15)0.0427 (15)−0.0020 (11)0.0145 (12)−0.0007 (12)
C150.0544 (18)0.0368 (15)0.0475 (16)0.0010 (13)0.0254 (14)−0.0052 (12)
C160.0520 (17)0.0494 (17)0.0483 (17)0.0005 (14)0.0281 (15)0.0023 (14)
C170.0412 (15)0.0390 (15)0.0422 (15)0.0020 (12)0.0154 (13)−0.0028 (12)
C180.0585 (19)0.0271 (14)0.0614 (19)−0.0043 (12)0.0250 (15)−0.0014 (13)
C190.063 (2)0.0368 (16)0.067 (2)−0.0039 (14)0.0330 (17)−0.0001 (14)
C200.081 (3)0.0498 (19)0.084 (3)−0.0122 (18)0.045 (2)0.0050 (18)
Geometric parameters (Å, °) top
O1—C11.353 (3)O4—C111.360 (3)
O1—H10.8206O4—H40.8191
O2—C71.210 (3)O5—C171.213 (3)
O3—C71.326 (3)O6—C171.328 (3)
O3—C81.449 (3)O6—C181.449 (3)
C1—C21.384 (4)C11—C161.381 (4)
C1—C61.385 (4)C11—C121.383 (4)
C2—C31.374 (4)C12—C131.369 (4)
C2—H20.9300C12—H120.9300
C3—C41.397 (4)C13—C141.389 (4)
C3—H30.9300C13—H130.9300
C4—C51.386 (4)C14—C151.387 (4)
C4—C71.478 (4)C14—C171.476 (4)
C5—C61.375 (4)C15—C161.381 (4)
C5—H50.9300C15—H150.9300
C6—H60.9300C16—H160.9300
C8—C91.497 (4)C18—C191.492 (4)
C8—H8A0.9700C18—H18A0.9700
C8—H8B0.9700C18—H18B0.9700
C9—C101.488 (5)C19—C201.523 (4)
C9—H9A0.9700C19—H19A0.9700
C9—H9B0.9700C19—H19B0.9700
C10—H10A0.9600C20—H20A0.9600
C10—H10B0.9600C20—H20B0.9600
C10—H10C0.9600C20—H20C0.9600
C1—O1—H1109.5C11—O4—H4109.5
C7—O3—C8117.4 (2)C17—O6—C18117.6 (2)
O1—C1—C2117.5 (3)O4—C11—C16122.4 (3)
O1—C1—C6122.8 (3)O4—C11—C12117.6 (3)
C2—C1—C6119.7 (3)C16—C11—C12120.0 (3)
C3—C2—C1120.4 (3)C13—C12—C11120.4 (3)
C3—C2—H2119.8C13—C12—H12119.8
C1—C2—H2119.8C11—C12—H12119.8
C2—C3—C4120.4 (3)C12—C13—C14120.7 (3)
C2—C3—H3119.8C12—C13—H13119.7
C4—C3—H3119.8C14—C13—H13119.7
C5—C4—C3118.5 (2)C15—C14—C13118.4 (3)
C5—C4—C7120.6 (2)C15—C14—C17120.1 (2)
C3—C4—C7120.8 (2)C13—C14—C17121.5 (2)
C6—C5—C4121.2 (3)C16—C15—C14121.3 (3)
C6—C5—H5119.4C16—C15—H15119.3
C4—C5—H5119.4C14—C15—H15119.3
C5—C6—C1119.8 (3)C15—C16—C11119.3 (3)
C5—C6—H6120.1C15—C16—H16120.4
C1—C6—H6120.1C11—C16—H16120.4
O2—C7—O3122.2 (3)O5—C17—O6122.3 (3)
O2—C7—C4124.8 (3)O5—C17—C14125.3 (3)
O3—C7—C4113.0 (2)O6—C17—C14112.4 (2)
O3—C8—C9107.6 (2)O6—C18—C19107.3 (2)
O3—C8—H8A110.2O6—C18—H18A110.3
C9—C8—H8A110.2C19—C18—H18A110.3
O3—C8—H8B110.2O6—C18—H18B110.3
C9—C8—H8B110.2C19—C18—H18B110.3
H8A—C8—H8B108.5H18A—C18—H18B108.5
C10—C9—C8112.5 (3)C18—C19—C20111.8 (3)
C10—C9—H9A109.1C18—C19—H19A109.3
C8—C9—H9A109.1C20—C19—H19A109.3
C10—C9—H9B109.1C18—C19—H19B109.3
C8—C9—H9B109.1C20—C19—H19B109.3
H9A—C9—H9B107.8H19A—C19—H19B107.9
C9—C10—H10A109.5C19—C20—H20A109.5
C9—C10—H10B109.5C19—C20—H20B109.5
H10A—C10—H10B109.5H20A—C20—H20B109.5
C9—C10—H10C109.5C19—C20—H20C109.5
H10A—C10—H10C109.5H20A—C20—H20C109.5
H10B—C10—H10C109.5H20B—C20—H20C109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O5i0.821.932.730 (3)167
O1—H1···O2ii0.821.912.720 (3)171
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O5i0.821.932.730 (3)167
O1—H1···O2ii0.821.912.720 (3)171
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+1/2.
Acknowledgements top

We would like to thank the National Nature Science Foundation of China (30971948) and Wuhan's program in science and technology (200760423155) for financial support for this work. We also wish to express our thanks to Meng Xianggao for his warmest help and patience.

references
References top

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.

Mandal, S. S. & Kadirvelraj, R. (1996). Chem. Commun. pp. 2725–2726.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.