Propyl 4-hydroxy­benzoate

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

doi:10.1107/S1600536810000139

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o485

https://doi.org/10.1107/S1600536810000139

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Propyl 4-hydroxybenzoate

Yiwen Zhou,^a Guzalnur Matsadiq,^a Yanling Wu,^a Jing Xiao ^a and Jing Cheng ^a ^*

^aKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: mdchengjing@126.com

(Received 4 December 2009; accepted 4 January 2010; online 30 January 2010)

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 π–π interactions between benzene rings [centroid–centroid distance = 4.040 (2) Å].

Related literature

For the structure of another p-hydroxybenzoate, see: Mandal & Kadirvelraj (1996 ).

Experimental

Crystal data

C₁₀H₁₂O₃
M_r = 180.20
Monoclinic, P 2₁ /c
a = 12.0634 (12) Å
b = 13.8419 (14) Å
c = 11.7982 (11) Å
β = 108.625 (2)°
V = 1866.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
10603 measured reflections
3271 independent reflections
2960 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.189
S = 1.27
3271 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5ⁱ	0.82	1.93	2.730 (3)	167
O1—H1⋯O2ⁱⁱ	0.82	1.91	2.720 (3)	171
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810000139/fk2009sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000139/fk2009Isup2.hkl

checkCIF report

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.

Structure description top

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

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

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

	Fig. 1. Molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing of (I), with O-H···O hydrogen bonds shown as dashed lines.

Propyl 4-hydroxybenzoate top

Crystal data top

C₁₀H₁₂O₃	F(000) = 768
M_r = 180.20	D_x = 1.282 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4791 reflections
a = 12.0634 (12) Å	θ = 2.3–28.3°
b = 13.8419 (14) Å	µ = 0.09 mm⁻¹
c = 11.7982 (11) Å	T = 298 K
β = 108.625 (2)°	Block, colourless
V = 1866.9 (3) Å³	0.30 × 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 tube	R_int = 0.027
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
0.3° wide ω exposures scans	h = −14→12
10603 measured reflections	k = −16→16
3271 independent reflections	l = −11→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.083	Hydrogen site location: geom and difmap
wR(F²) = 0.189	H-atom parameters constrained
S = 1.27	w = 1/[σ²(F_o²) + (0.0626P)² + 1.2781P] where P = (F_o² + 2F_c²)/3
3271 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₀H₁₂O₃	V = 1866.9 (3) Å³
M_r = 180.20	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0634 (12) Å	µ = 0.09 mm⁻¹
b = 13.8419 (14) Å	T = 298 K
c = 11.7982 (11) Å	0.30 × 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 reflections	R_int = 0.027
3271 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.27	Δρ_max = 0.24 e Å⁻³
3271 reflections	Δρ_min = −0.30 e Å⁻³
237 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.9740 (2)	0.97287 (14)	0.3245 (2)	0.0657 (7)
H1	1.0093	0.9797	0.2760	0.098*
O2	0.9063 (2)	0.51536 (14)	0.3293 (2)	0.0608 (6)
O3	0.82019 (18)	0.56944 (13)	0.45749 (18)	0.0488 (5)
C1	0.9519 (3)	0.87795 (19)	0.3346 (3)	0.0447 (7)
C2	0.8980 (3)	0.8521 (2)	0.4176 (3)	0.0545 (8)
H2	0.8777	0.8996	0.4631	0.065*
C3	0.8744 (3)	0.75689 (19)	0.4330 (3)	0.0461 (7)
H3	0.8381	0.7403	0.4890	0.055*
C4	0.9044 (2)	0.68486 (19)	0.3652 (2)	0.0370 (6)
C5	0.9577 (3)	0.7118 (2)	0.2820 (3)	0.0460 (7)
H5	0.9781	0.6646	0.2362	0.055*
C6	0.9810 (3)	0.8072 (2)	0.2660 (3)	0.0467 (7)
H6	1.0162	0.8242	0.2093	0.056*
C7	0.8785 (2)	0.5822 (2)	0.3806 (3)	0.0403 (7)
C8	0.7870 (3)	0.4715 (2)	0.4759 (3)	0.0527 (8)
H8A	0.8560	0.4335	0.5156	0.063*
H8B	0.7463	0.4414	0.3997	0.063*
C9	0.7087 (4)	0.4766 (2)	0.5519 (3)	0.0672 (10)
H9A	0.7509	0.5067	0.6277	0.081*
H9B	0.6418	0.5170	0.5124	0.081*
C10	0.6668 (4)	0.3798 (3)	0.5749 (4)	0.0862 (13)
H10A	0.6203	0.3516	0.5006	0.129*
H10B	0.6202	0.3864	0.6270	0.129*
H10C	0.7327	0.3389	0.6120	0.129*
O4	0.5717 (2)	0.61479 (15)	0.7201 (2)	0.0742 (8)
H4	0.5298	0.6082	0.7622	0.111*
O5	0.5895 (2)	1.07375 (15)	0.6687 (2)	0.0594 (6)
O6	0.68661 (18)	1.01843 (13)	0.55031 (18)	0.0492 (5)
C11	0.5838 (3)	0.7104 (2)	0.7005 (3)	0.0482 (7)
C12	0.6369 (3)	0.7352 (2)	0.6165 (3)	0.0610 (9)
H12	0.6633	0.6871	0.5766	0.073*
C13	0.6507 (3)	0.8303 (2)	0.5919 (3)	0.0497 (8)
H13	0.6860	0.8462	0.5349	0.060*
C14	0.6125 (2)	0.9033 (2)	0.6512 (2)	0.0385 (6)
C15	0.5595 (3)	0.8775 (2)	0.7353 (3)	0.0441 (7)
H15	0.5335	0.9256	0.7757	0.053*
C16	0.5447 (3)	0.7818 (2)	0.7602 (3)	0.0470 (7)
H16	0.5088	0.7656	0.8166	0.056*
C17	0.6265 (2)	1.0062 (2)	0.6259 (2)	0.0403 (7)
C18	0.7092 (3)	1.11661 (19)	0.5211 (3)	0.0476 (7)
H18A	0.7597	1.1491	0.5916	0.057*
H18B	0.6365	1.1524	0.4918	0.057*
C19	0.7673 (3)	1.1111 (2)	0.4270 (3)	0.0526 (8)
H19A	0.7162	1.0776	0.3577	0.063*
H19B	0.8390	1.0741	0.4571	0.063*
C20	0.7954 (3)	1.2110 (2)	0.3895 (3)	0.0672 (10)
H20A	0.7243	1.2470	0.3571	0.101*
H20B	0.8337	1.2047	0.3300	0.101*
H20C	0.8461	1.2443	0.4579	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1019 (19)	0.0285 (11)	0.0922 (17)	−0.0029 (11)	0.0670 (15)	0.0030 (11)
O2	0.0824 (16)	0.0342 (11)	0.0856 (16)	−0.0030 (10)	0.0544 (14)	−0.0113 (11)
O3	0.0671 (14)	0.0298 (10)	0.0629 (13)	−0.0052 (9)	0.0393 (11)	−0.0006 (9)
C1	0.0551 (18)	0.0306 (14)	0.0554 (18)	−0.0010 (12)	0.0275 (15)	0.0017 (12)
C2	0.078 (2)	0.0349 (15)	0.069 (2)	0.0015 (15)	0.0485 (18)	−0.0054 (14)
C3	0.0614 (19)	0.0340 (15)	0.0558 (18)	−0.0001 (13)	0.0370 (16)	0.0031 (12)
C4	0.0394 (15)	0.0325 (14)	0.0419 (15)	−0.0006 (11)	0.0168 (12)	−0.0009 (11)
C5	0.0575 (18)	0.0392 (15)	0.0520 (17)	−0.0024 (13)	0.0325 (15)	−0.0083 (13)
C6	0.0606 (19)	0.0425 (16)	0.0486 (17)	−0.0022 (14)	0.0337 (15)	0.0032 (13)
C7	0.0398 (15)	0.0372 (15)	0.0479 (16)	0.0008 (12)	0.0198 (13)	−0.0033 (12)
C8	0.068 (2)	0.0302 (15)	0.066 (2)	−0.0044 (14)	0.0305 (17)	0.0049 (13)
C9	0.101 (3)	0.0448 (18)	0.072 (2)	−0.0123 (18)	0.051 (2)	−0.0045 (16)
C10	0.121 (4)	0.063 (2)	0.099 (3)	−0.018 (2)	0.070 (3)	0.000 (2)
O4	0.107 (2)	0.0348 (12)	0.111 (2)	−0.0041 (12)	0.0776 (17)	0.0060 (12)
O5	0.0821 (16)	0.0367 (12)	0.0756 (15)	0.0051 (10)	0.0478 (13)	−0.0039 (10)
O6	0.0660 (13)	0.0292 (10)	0.0655 (13)	−0.0020 (9)	0.0395 (11)	−0.0008 (9)
C11	0.0502 (17)	0.0375 (15)	0.0637 (19)	−0.0021 (13)	0.0279 (15)	0.0039 (14)
C12	0.079 (2)	0.0347 (16)	0.093 (3)	0.0007 (15)	0.061 (2)	−0.0071 (16)
C13	0.0618 (19)	0.0394 (16)	0.065 (2)	−0.0035 (14)	0.0435 (17)	−0.0034 (14)
C14	0.0347 (14)	0.0397 (15)	0.0427 (15)	−0.0020 (11)	0.0145 (12)	−0.0007 (12)
C15	0.0544 (18)	0.0368 (15)	0.0475 (16)	0.0010 (13)	0.0254 (14)	−0.0052 (12)
C16	0.0520 (17)	0.0494 (17)	0.0483 (17)	0.0005 (14)	0.0281 (15)	0.0023 (14)
C17	0.0412 (15)	0.0390 (15)	0.0422 (15)	0.0020 (12)	0.0154 (13)	−0.0028 (12)
C18	0.0585 (19)	0.0271 (14)	0.0614 (19)	−0.0043 (12)	0.0250 (15)	−0.0014 (13)
C19	0.063 (2)	0.0368 (16)	0.067 (2)	−0.0039 (14)	0.0330 (17)	−0.0001 (14)
C20	0.081 (3)	0.0498 (19)	0.084 (3)	−0.0122 (18)	0.045 (2)	0.0050 (18)

Geometric parameters (Å, º) top

O1—C1	1.353 (3)	O4—C11	1.360 (3)
O1—H1	0.8206	O4—H4	0.8191
O2—C7	1.210 (3)	O5—C17	1.213 (3)
O3—C7	1.326 (3)	O6—C17	1.328 (3)
O3—C8	1.449 (3)	O6—C18	1.449 (3)
C1—C2	1.384 (4)	C11—C16	1.381 (4)
C1—C6	1.385 (4)	C11—C12	1.383 (4)
C2—C3	1.374 (4)	C12—C13	1.369 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.397 (4)	C13—C14	1.389 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.386 (4)	C14—C15	1.387 (4)
C4—C7	1.478 (4)	C14—C17	1.476 (4)
C5—C6	1.375 (4)	C15—C16	1.381 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300
C8—C9	1.497 (4)	C18—C19	1.492 (4)
C8—H8A	0.9700	C18—H18A	0.9700
C8—H8B	0.9700	C18—H18B	0.9700
C9—C10	1.488 (5)	C19—C20	1.523 (4)
C9—H9A	0.9700	C19—H19A	0.9700
C9—H9B	0.9700	C19—H19B	0.9700
C10—H10A	0.9600	C20—H20A	0.9600
C10—H10B	0.9600	C20—H20B	0.9600
C10—H10C	0.9600	C20—H20C	0.9600

C1—O1—H1	109.5	C11—O4—H4	109.5
C7—O3—C8	117.4 (2)	C17—O6—C18	117.6 (2)
O1—C1—C2	117.5 (3)	O4—C11—C16	122.4 (3)
O1—C1—C6	122.8 (3)	O4—C11—C12	117.6 (3)
C2—C1—C6	119.7 (3)	C16—C11—C12	120.0 (3)
C3—C2—C1	120.4 (3)	C13—C12—C11	120.4 (3)
C3—C2—H2	119.8	C13—C12—H12	119.8
C1—C2—H2	119.8	C11—C12—H12	119.8
C2—C3—C4	120.4 (3)	C12—C13—C14	120.7 (3)
C2—C3—H3	119.8	C12—C13—H13	119.7
C4—C3—H3	119.8	C14—C13—H13	119.7
C5—C4—C3	118.5 (2)	C15—C14—C13	118.4 (3)
C5—C4—C7	120.6 (2)	C15—C14—C17	120.1 (2)
C3—C4—C7	120.8 (2)	C13—C14—C17	121.5 (2)
C6—C5—C4	121.2 (3)	C16—C15—C14	121.3 (3)
C6—C5—H5	119.4	C16—C15—H15	119.3
C4—C5—H5	119.4	C14—C15—H15	119.3
C5—C6—C1	119.8 (3)	C15—C16—C11	119.3 (3)
C5—C6—H6	120.1	C15—C16—H16	120.4
C1—C6—H6	120.1	C11—C16—H16	120.4
O2—C7—O3	122.2 (3)	O5—C17—O6	122.3 (3)
O2—C7—C4	124.8 (3)	O5—C17—C14	125.3 (3)
O3—C7—C4	113.0 (2)	O6—C17—C14	112.4 (2)
O3—C8—C9	107.6 (2)	O6—C18—C19	107.3 (2)
O3—C8—H8A	110.2	O6—C18—H18A	110.3
C9—C8—H8A	110.2	C19—C18—H18A	110.3
O3—C8—H8B	110.2	O6—C18—H18B	110.3
C9—C8—H8B	110.2	C19—C18—H18B	110.3
H8A—C8—H8B	108.5	H18A—C18—H18B	108.5
C10—C9—C8	112.5 (3)	C18—C19—C20	111.8 (3)
C10—C9—H9A	109.1	C18—C19—H19A	109.3
C8—C9—H9A	109.1	C20—C19—H19A	109.3
C10—C9—H9B	109.1	C18—C19—H19B	109.3
C8—C9—H9B	109.1	C20—C19—H19B	109.3
H9A—C9—H9B	107.8	H19A—C19—H19B	107.9
C9—C10—H10A	109.5	C19—C20—H20A	109.5
C9—C10—H10B	109.5	C19—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C9—C10—H10C	109.5	C19—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ⁱ	0.82	1.93	2.730 (3)	167
O1—H1···O2ⁱⁱ	0.82	1.91	2.720 (3)	171

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂O₃
M_r	180.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.0634 (12), 13.8419 (14), 11.7982 (11)
β (°)	108.625 (2)
V (Å³)	1866.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10603, 3271, 2960
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.189, 1.27
No. of reflections	3271
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.30

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ⁱ	0.82	1.93	2.730 (3)	166.7
O1—H1···O2ⁱⁱ	0.82	1.91	2.720 (3)	171.4

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+1/2.

Acknowledgements

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.

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