Propyl 4-hydroxy-benzoate.

There are two mol-ecules in the asymmetric unit of the title compound, C(10)H(12)O(3). In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds into chains running along [010]. Adjacent chains are joined together by weak π-π inter-actions 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 = 180.20

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.189

S = 1.27

3271 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000139/fk2009Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H12O3	F(000) = 768
Mr = 180.20	Dx = 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

Bruker SMART APEX CCD area-detector diffractometer	2960 reflections with I > 2σ(I)
Radiation source: fine focus sealed Siemens Mo tube	Rint = 0.027
graphite	θmax = 25.0°, θmin = 2.3°
0.3° wide ω exposures scans	h = −14→12
10603 measured reflections	k = −16→16
3271 independent reflections	l = −11→14

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(Fo2) + (0.0626P)2 + 1.2781P] where P = (Fo2 + 2Fc2)/3
3271 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) .