2-Hy-droxy-4-(prop-2-yn-yloxy)benz-alde-hyde.

The asymmetric unit of the title compound, C10H8O3, contains two independent mol-ecules, both of which are almost planar (r.m.s deviations for all non-H atoms of 0.044 and 0.053 Å). The dihedral angles between the benzene ring and the prop-1-yne group are 3.47 (1) and 3.07 (1)° in the two mol-ecules, and the prop-1-yne groups adopt extended conformations. In each mol-ecule, an intra-molecular O-H⋯O hydrogen bond involving the OH and aldehyde substituents forms an S(6) ring. In the crystal, mol-ecules are linked into cyclic centrosymmetric dimers via C-H⋯O hydrogen bonds, generating R2(2)(14) ring motifs. The crystal structure is further stabilized by aromatic π-π stacking inter-actions between the benzene rings [centroid-centroid distances = 3.813 (2) and 3.843 (2) Å].

Related literature

For the biological activity of benzaldehyde derivatives, see: Zhao et al. (2007 ▶); Ley & Bertram (2001 ▶); Delogu et al. (2010 ▶). For a related structure see: Esakkiammal et al. (2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995) ▶.

Experimental

Crystal data

C10H8O3

M = 176.16

Triclinic,

a = 7.0835 (5) Å

b = 10.4059 (7) Å

c = 12.8461 (8) Å

α = 73.910 (3)°

β = 89.756 (4)°

γ = 73.436 (4)°

V = 869.16 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

15699 measured reflections

4347 independent reflections

2880 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.132

S = 1.05

4347 reflections

243 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012) ▶; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049598/sj5285sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049598/sj5285Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049598/sj5285Isup3.cml

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

C10H8O3	Z = 4
Mr = 176.16	F(000) = 368
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0835 (5) Å	Cell parameters from 4347 reflections
b = 10.4059 (7) Å	θ = 1.7–28.4°
c = 12.8461 (8) Å	µ = 0.10 mm−1
α = 73.910 (3)°	T = 293 K
β = 89.756 (4)°	Block, colourless
γ = 73.436 (4)°	0.20 × 0.20 × 0.20 mm
V = 869.16 (10) Å3

Bruker SMART APEXII area-detector diffractometer	2880 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 28.4°, θmin = 1.7°
ω and φ scans	h = −9→9
15699 measured reflections	k = −13→13
4347 independent reflections	l = −17→17

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.0997P] where P = (Fo2 + 2Fc2)/3
4347 reflections	(Δ/σ)max < 0.001
243 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.20 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
O4	0.23016 (15)	0.81458 (9)	0.55793 (7)	0.0528 (3)
C14	0.2775 (2)	0.69318 (13)	0.41998 (10)	0.0473 (3)
H14	0.3173	0.6058	0.4713	0.057*
O5	0.31664 (18)	0.58412 (11)	0.28152 (9)	0.0699 (3)
H5	0.3065	0.6028	0.2151	0.105*
C16	0.1668 (2)	0.94571 (13)	0.37621 (11)	0.0498 (3)
H16	0.1326	1.0264	0.3987	0.060*
C15	0.22699 (19)	0.81361 (13)	0.45238 (10)	0.0423 (3)
C12	0.2087 (2)	0.83519 (14)	0.23261 (10)	0.0473 (3)
O6	0.2396 (2)	0.74928 (15)	0.07950 (9)	0.0831 (4)
C13	0.2683 (2)	0.70387 (14)	0.31045 (11)	0.0467 (3)
C11	0.1590 (2)	0.95453 (14)	0.26846 (11)	0.0511 (3)
H11	0.1196	1.0423	0.2175	0.061*
C18	0.2822 (3)	0.68218 (15)	0.63841 (11)	0.0639 (4)
H18A	0.4161	0.6290	0.6314	0.077*
H18B	0.1940	0.6296	0.6284	0.077*
C19	0.2680 (2)	0.70303 (15)	0.74570 (12)	0.0546 (4)
C17	0.1995 (2)	0.84683 (19)	0.11911 (12)	0.0643 (4)
H17	0.1594	0.9367	0.0712	0.077*
C20	0.2593 (3)	0.71369 (18)	0.83353 (13)	0.0652 (4)
O1	0.27472 (15)	0.21006 (10)	0.97384 (7)	0.0556 (3)
C4	0.2102 (2)	0.31928 (13)	0.77968 (10)	0.0480 (3)
H4	0.1643	0.4086	0.7881	0.058*
C6	0.3435 (2)	0.06902 (13)	0.85818 (11)	0.0475 (3)
H6	0.3856	−0.0081	0.9192	0.057*
C5	0.27430 (19)	0.20366 (13)	0.86926 (10)	0.0426 (3)
C3	0.2154 (2)	0.30031 (13)	0.67725 (10)	0.0458 (3)
C2	0.28516 (19)	0.16624 (13)	0.66383 (10)	0.0442 (3)
C1	0.3487 (2)	0.05198 (14)	0.75674 (11)	0.0480 (3)
H1	0.3956	−0.0377	0.7491	0.058*
O2	0.15146 (18)	0.41492 (10)	0.59107 (7)	0.0675 (3)
H2	0.1609	0.3914	0.5349	0.101*
O3	0.2389 (2)	0.23901 (13)	0.47217 (8)	0.0756 (4)
C7	0.2915 (2)	0.14587 (18)	0.55809 (12)	0.0594 (4)
H7	0.3396	0.0544	0.5542	0.071*
C9	0.2226 (2)	0.32905 (16)	1.10635 (12)	0.0576 (4)
C8	0.2136 (3)	0.34536 (16)	0.99018 (12)	0.0664 (4)
H8A	0.0797	0.3946	0.9582	0.080*
H8B	0.2996	0.3995	0.9556	0.080*
C10	0.2270 (3)	0.3192 (2)	1.19909 (14)	0.0684 (5)
H10	0.230 (3)	0.3082 (19)	1.2682 (16)	0.088 (6)*
H20	0.253 (2)	0.7250 (17)	0.9014 (15)	0.078 (5)*

	U11	U22	U33	U12	U13	U23
O4	0.0719 (7)	0.0437 (5)	0.0408 (5)	−0.0109 (4)	0.0031 (4)	−0.0153 (4)
C14	0.0586 (8)	0.0379 (6)	0.0406 (7)	−0.0080 (6)	0.0023 (6)	−0.0100 (5)
O5	0.0999 (9)	0.0533 (6)	0.0531 (6)	−0.0056 (6)	0.0018 (6)	−0.0275 (5)
C16	0.0560 (8)	0.0390 (7)	0.0518 (8)	−0.0098 (6)	0.0033 (6)	−0.0134 (6)
C15	0.0445 (7)	0.0427 (7)	0.0397 (6)	−0.0110 (5)	0.0038 (5)	−0.0137 (5)
C12	0.0456 (7)	0.0545 (8)	0.0400 (7)	−0.0149 (6)	0.0048 (6)	−0.0106 (6)
O6	0.1047 (10)	0.1030 (10)	0.0461 (6)	−0.0269 (8)	0.0113 (6)	−0.0326 (7)
C13	0.0496 (8)	0.0453 (7)	0.0448 (7)	−0.0095 (6)	0.0041 (6)	−0.0170 (6)
C11	0.0547 (8)	0.0428 (7)	0.0473 (7)	−0.0116 (6)	0.0008 (6)	−0.0025 (6)
C18	0.0978 (12)	0.0474 (8)	0.0417 (7)	−0.0147 (8)	−0.0004 (7)	−0.0118 (6)
C19	0.0653 (9)	0.0533 (8)	0.0459 (8)	−0.0192 (7)	0.0014 (7)	−0.0134 (6)
C17	0.0681 (10)	0.0793 (11)	0.0416 (8)	−0.0221 (8)	0.0062 (7)	−0.0110 (8)
C20	0.0841 (12)	0.0716 (10)	0.0446 (8)	−0.0277 (9)	0.0068 (8)	−0.0195 (8)
O1	0.0775 (7)	0.0464 (5)	0.0335 (5)	−0.0063 (5)	−0.0011 (4)	−0.0091 (4)
C4	0.0655 (9)	0.0367 (6)	0.0382 (7)	−0.0110 (6)	−0.0009 (6)	−0.0093 (5)
C6	0.0544 (8)	0.0390 (6)	0.0422 (7)	−0.0094 (6)	0.0008 (6)	−0.0051 (5)
C5	0.0475 (7)	0.0426 (7)	0.0342 (6)	−0.0106 (5)	0.0010 (5)	−0.0083 (5)
C3	0.0587 (8)	0.0418 (7)	0.0359 (6)	−0.0192 (6)	−0.0013 (6)	−0.0051 (5)
C2	0.0495 (7)	0.0477 (7)	0.0412 (7)	−0.0213 (6)	0.0059 (6)	−0.0150 (5)
C1	0.0528 (8)	0.0392 (7)	0.0524 (8)	−0.0121 (6)	0.0050 (6)	−0.0154 (6)
O2	0.1155 (10)	0.0468 (6)	0.0338 (5)	−0.0239 (6)	−0.0080 (5)	−0.0015 (4)
O3	0.1107 (10)	0.0851 (8)	0.0383 (6)	−0.0384 (7)	0.0061 (6)	−0.0197 (6)
C7	0.0737 (10)	0.0662 (9)	0.0500 (8)	−0.0290 (8)	0.0105 (7)	−0.0264 (7)
C9	0.0645 (10)	0.0590 (9)	0.0495 (8)	−0.0133 (7)	0.0022 (7)	−0.0212 (7)
C8	0.0962 (12)	0.0514 (8)	0.0438 (8)	−0.0067 (8)	0.0006 (8)	−0.0167 (6)
C10	0.0784 (12)	0.0844 (12)	0.0474 (9)	−0.0227 (9)	0.0045 (8)	−0.0286 (8)

O4—C15	1.3591 (14)	O1—C5	1.3634 (14)
O4—C18	1.4237 (16)	O1—C8	1.4245 (16)
C14—C15	1.3798 (17)	C4—C5	1.3797 (17)
C14—C13	1.3806 (18)	C4—C3	1.3825 (18)
C14—H14	0.9300	C4—H4	0.9300
O5—C13	1.3493 (15)	C6—C1	1.3619 (18)
O5—H5	0.8200	C6—C5	1.3935 (17)
C16—C11	1.3619 (18)	C6—H6	0.9300
C16—C15	1.3974 (17)	C3—O2	1.3481 (15)
C16—H16	0.9300	C3—C2	1.3999 (18)
C12—C11	1.3944 (19)	C2—C1	1.3977 (18)
C12—C13	1.4010 (19)	C2—C7	1.4304 (18)
C12—C17	1.4295 (19)	C1—H1	0.9300
O6—C17	1.221 (2)	O2—H2	0.8200
C11—H11	0.9300	O3—C7	1.2251 (19)
C18—C19	1.4522 (19)	C7—H7	0.9300
C18—H18A	0.9700	C9—C10	1.167 (2)
C18—H18B	0.9700	C9—C8	1.454 (2)
C19—C20	1.164 (2)	C8—H8A	0.9700
C17—H17	0.9300	C8—H8B	0.9700
C20—H20	0.911 (18)	C10—H10	0.862 (19)
C15—O4—C18	116.91 (10)	C5—O1—C8	117.38 (10)
C15—C14—C13	119.27 (12)	C5—C4—C3	119.00 (12)
C15—C14—H14	120.4	C5—C4—H4	120.5
C13—C14—H14	120.4	C3—C4—H4	120.5
C13—O5—H5	109.5	C1—C6—C5	119.09 (11)
C11—C16—C15	118.97 (12)	C1—C6—H6	120.5
C11—C16—H16	120.5	C5—C6—H6	120.5
C15—C16—H16	120.5	O1—C5—C4	123.96 (11)
O4—C15—C14	123.91 (11)	O1—C5—C6	114.78 (10)
O4—C15—C16	115.03 (11)	C4—C5—C6	121.26 (12)
C14—C15—C16	121.06 (12)	O2—C3—C4	117.85 (12)
C11—C12—C13	118.41 (12)	O2—C3—C2	121.27 (11)
C11—C12—C17	120.70 (13)	C4—C3—C2	120.88 (12)
C13—C12—C17	120.89 (13)	C1—C2—C3	118.26 (11)
O5—C13—C14	117.79 (12)	C1—C2—C7	120.55 (12)
O5—C13—C12	121.53 (12)	C3—C2—C7	121.19 (12)
C14—C13—C12	120.67 (12)	C6—C1—C2	121.50 (12)
C16—C11—C12	121.62 (12)	C6—C1—H1	119.2
C16—C11—H11	119.2	C2—C1—H1	119.2
C12—C11—H11	119.2	C3—O2—H2	109.5
O4—C18—C19	109.46 (11)	O3—C7—C2	125.35 (14)
O4—C18—H18A	109.8	O3—C7—H7	117.3
C19—C18—H18A	109.8	C2—C7—H7	117.3
O4—C18—H18B	109.8	C10—C9—C8	178.40 (17)
C19—C18—H18B	109.8	O1—C8—C9	108.67 (12)
H18A—C18—H18B	108.2	O1—C8—H8A	110.0
C20—C19—C18	177.13 (16)	C9—C8—H8A	110.0
O6—C17—C12	125.79 (15)	O1—C8—H8B	110.0
O6—C17—H17	117.1	C9—C8—H8B	110.0
C12—C17—H17	117.1	H8A—C8—H8B	108.3
C19—C20—H20	178.1 (11)	C9—C10—H10	177.5 (13)
C18—O4—C15—C14	−2.4 (2)	C8—O1—C5—C4	−3.0 (2)
C18—O4—C15—C16	177.32 (13)	C8—O1—C5—C6	177.38 (12)
C13—C14—C15—O4	179.71 (12)	C3—C4—C5—O1	−179.63 (12)
C13—C14—C15—C16	0.0 (2)	C3—C4—C5—C6	0.0 (2)
C11—C16—C15—O4	−179.91 (12)	C1—C6—C5—O1	180.00 (12)
C11—C16—C15—C14	−0.2 (2)	C1—C6—C5—C4	0.4 (2)
C15—C14—C13—O5	−179.31 (12)	C5—C4—C3—O2	179.81 (13)
C15—C14—C13—C12	0.0 (2)	C5—C4—C3—C2	−0.3 (2)
C11—C12—C13—O5	179.36 (13)	O2—C3—C2—C1	−179.83 (13)
C17—C12—C13—O5	−0.9 (2)	C4—C3—C2—C1	0.3 (2)
C11—C12—C13—C14	0.0 (2)	O2—C3—C2—C7	0.1 (2)
C17—C12—C13—C14	179.81 (13)	C4—C3—C2—C7	−179.79 (13)
C15—C16—C11—C12	0.3 (2)	C5—C6—C1—C2	−0.4 (2)
C13—C12—C11—C16	−0.2 (2)	C3—C2—C1—C6	0.1 (2)
C17—C12—C11—C16	−179.99 (13)	C7—C2—C1—C6	−179.87 (13)
C15—O4—C18—C19	−177.04 (12)	C1—C2—C7—O3	179.84 (15)
O4—C18—C19—C20	−179 (100)	C3—C2—C7—O3	−0.1 (2)
C11—C12—C17—O6	−179.95 (16)	C5—O1—C8—C9	179.39 (13)
C13—C12—C17—O6	0.3 (3)	C10—C9—C8—O1	−162 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.92	2.6387 (16)	146
O5—H5···O6	0.82	1.93	2.6441 (16)	146
C10—H10···O3i	0.86 (2)	2.51 (2)	3.369 (2)	171.4 (2)
C18—H18A···O5ii	0.97	2.45	3.281 (2)	144
C20—H20···O6i	0.91 (2)	2.37 (2)	3.280 (2)	178.8 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.92	2.6387 (16)	146
O5—H5⋯O6	0.82	1.93	2.6441 (16)	146
C10—H10⋯O3i	0.86 (2)	2.51 (2)	3.369 (2)	171.4 (2)
C18—H18A⋯O5ii	0.97	2.45	3.281 (2)	144
C20—H20⋯O6i	0.91 (2)	2.37 (2)	3.280 (2)	178.8 (2)

Symmetry codes: (i) ; (ii) .