2,4-Bis[(prop-2-yn-yl)-oxy]benzaldehyde.

In the title compound, C(13)H(10)O(3), two prop-2-yn-yloxy groups are attached to the benzaldehyde ring at positions 2 and 6. The crystal packing features C-H⋯O inter-actions.

Related literature

For the biological activity of benzaldehyde derivatives, see: Zhao et al. (2007 ▶). For related literature, see: Delogu et al. (2010 ▶); Ley & Bertram (2001 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10O3

M = 214.21

Monoclinic,

a = 4.9219 (2) Å

b = 16.8705 (7) Å

c = 13.4326 (6) Å

β = 98.236 (3)°

V = 1103.87 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.982, T max = 0.982

10446 measured reflections

2754 independent reflections

2177 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.04

2754 reflections

154 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031637/bt5961sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031637/bt5961Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031637/bt5961Isup3.cml

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

C13H10O3	F(000) = 448
Mr = 214.21	Dx = 1.289 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2754 reflections
a = 4.9219 (2) Å	θ = 2.0–28.4°
b = 16.8705 (7) Å	µ = 0.09 mm−1
c = 13.4326 (6) Å	T = 293 K
β = 98.236 (3)°	Block, colourless
V = 1103.87 (8) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	2754 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
Tmin = 0.982, Tmax = 0.982	k = −22→22
10446 measured reflections	l = −16→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.1741P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2754 reflections	Δρmax = 0.25 e Å−3
154 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (4)

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
O2	0.05286 (17)	0.31557 (5)	0.65108 (6)	0.0445 (2)
O3	0.68295 (18)	0.16361 (5)	0.49674 (7)	0.0501 (3)
O1	0.0285 (2)	0.15987 (5)	0.87280 (7)	0.0554 (3)
C6	0.3759 (2)	0.23786 (7)	0.57231 (9)	0.0396 (3)
H6	0.3799	0.2751	0.5214	0.047*
C2	0.2097 (2)	0.19456 (6)	0.72497 (8)	0.0376 (3)
C3	0.3673 (2)	0.12642 (7)	0.72331 (9)	0.0430 (3)
H3	0.3642	0.0890	0.7739	0.052*
C4	0.5284 (2)	0.11234 (7)	0.64902 (9)	0.0447 (3)
H4	0.6320	0.0662	0.6492	0.054*
C9	−0.1318 (3)	0.43691 (7)	0.59180 (9)	0.0447 (3)
C7	0.2148 (2)	0.25048 (6)	0.64716 (8)	0.0361 (2)
C5	0.5317 (2)	0.16901 (7)	0.57387 (9)	0.0398 (3)
C12	0.9705 (3)	0.09766 (8)	0.40030 (11)	0.0554 (3)
C1	0.0455 (3)	0.20717 (7)	0.80598 (9)	0.0459 (3)
H1	−0.0521	0.2544	0.8063	0.055*
C10	−0.2730 (3)	0.49054 (8)	0.60585 (11)	0.0539 (3)
C11	0.8314 (3)	0.09202 (8)	0.48871 (10)	0.0495 (3)
H11A	0.7066	0.0472	0.4822	0.059*
H11B	0.9646	0.0844	0.5485	0.059*
C8	0.0455 (3)	0.37140 (7)	0.57073 (9)	0.0453 (3)
H8A	−0.0264	0.3465	0.5073	0.054*
H8B	0.2290	0.3907	0.5663	0.054*
C13	1.0861 (4)	0.10046 (11)	0.33041 (14)	0.0791 (5)
H10	−0.379 (4)	0.5352 (11)	0.6156 (14)	0.087 (6)*
H13	1.176 (5)	0.1042 (13)	0.2780 (18)	0.114 (7)*

	U11	U22	U33	U12	U13	U23
O2	0.0548 (5)	0.0381 (4)	0.0443 (5)	0.0099 (4)	0.0197 (4)	0.0088 (3)
O3	0.0517 (5)	0.0511 (5)	0.0520 (5)	0.0140 (4)	0.0224 (4)	0.0074 (4)
O1	0.0824 (7)	0.0460 (5)	0.0421 (5)	−0.0069 (4)	0.0231 (5)	0.0041 (4)
C6	0.0420 (6)	0.0392 (6)	0.0391 (6)	0.0024 (5)	0.0107 (5)	0.0070 (5)
C2	0.0419 (6)	0.0363 (6)	0.0351 (5)	−0.0024 (4)	0.0070 (4)	0.0019 (4)
C3	0.0493 (7)	0.0398 (6)	0.0400 (6)	0.0020 (5)	0.0068 (5)	0.0085 (5)
C4	0.0453 (6)	0.0406 (6)	0.0484 (7)	0.0091 (5)	0.0081 (5)	0.0052 (5)
C9	0.0512 (7)	0.0403 (6)	0.0432 (6)	0.0027 (5)	0.0090 (5)	0.0061 (5)
C7	0.0376 (5)	0.0335 (5)	0.0377 (6)	0.0004 (4)	0.0072 (4)	0.0020 (4)
C5	0.0361 (5)	0.0439 (6)	0.0402 (6)	0.0021 (4)	0.0089 (4)	0.0009 (5)
C12	0.0588 (8)	0.0540 (8)	0.0555 (8)	0.0105 (6)	0.0152 (6)	−0.0073 (6)
C1	0.0597 (7)	0.0398 (6)	0.0409 (6)	−0.0003 (5)	0.0158 (5)	0.0017 (5)
C10	0.0645 (8)	0.0434 (7)	0.0551 (8)	0.0106 (6)	0.0129 (6)	0.0036 (6)
C11	0.0487 (7)	0.0486 (7)	0.0533 (7)	0.0094 (5)	0.0146 (6)	−0.0023 (6)
C8	0.0520 (7)	0.0425 (6)	0.0437 (6)	0.0085 (5)	0.0147 (5)	0.0105 (5)
C13	0.0998 (13)	0.0800 (12)	0.0659 (10)	0.0122 (10)	0.0402 (10)	−0.0076 (9)

O2—C7	1.3622 (13)	C4—C5	1.3922 (16)
O2—C8	1.4292 (14)	C4—H4	0.9300
O3—C5	1.3626 (13)	C9—C10	1.1722 (18)
O3—C11	1.4235 (14)	C9—C8	1.4608 (16)
O1—C1	1.2127 (14)	C12—C13	1.166 (2)
C6—C7	1.3832 (15)	C12—C11	1.4565 (18)
C6—C5	1.3905 (15)	C1—H1	0.9300
C6—H6	0.9300	C10—H10	0.935 (19)
C2—C3	1.3886 (16)	C11—H11A	0.9700
C2—C7	1.4109 (15)	C11—H11B	0.9700
C2—C1	1.4611 (15)	C8—H8A	0.9700
C3—C4	1.3814 (17)	C8—H8B	0.9700
C3—H3	0.9300	C13—H13	0.89 (2)
C7—O2—C8	116.99 (8)	C6—C5—C4	121.39 (10)
C5—O3—C11	117.16 (9)	C13—C12—C11	178.21 (17)
C7—C6—C5	119.35 (10)	O1—C1—C2	124.02 (11)
C7—C6—H6	120.3	O1—C1—H1	118.0
C5—C6—H6	120.3	C2—C1—H1	118.0
C3—C2—C7	118.20 (10)	C9—C10—H10	176.8 (12)
C3—C2—C1	120.16 (10)	O3—C11—C12	108.22 (11)
C7—C2—C1	121.65 (10)	O3—C11—H11A	110.1
C4—C3—C2	122.26 (11)	C12—C11—H11A	110.1
C4—C3—H3	118.9	O3—C11—H11B	110.1
C2—C3—H3	118.9	C12—C11—H11B	110.1
C3—C4—C5	118.25 (11)	H11A—C11—H11B	108.4
C3—C4—H4	120.9	O2—C8—C9	107.67 (9)
C5—C4—H4	120.9	O2—C8—H8A	110.2
C10—C9—C8	177.88 (13)	C9—C8—H8A	110.2
O2—C7—C6	123.48 (9)	O2—C8—H8B	110.2
O2—C7—C2	115.97 (9)	C9—C8—H8B	110.2
C6—C7—C2	120.55 (10)	H8A—C8—H8B	108.5
O3—C5—C6	113.87 (10)	C12—C13—H13	178.1 (16)
O3—C5—C4	124.74 (10)
C7—C2—C3—C4	0.52 (18)	C11—O3—C5—C4	4.98 (17)
C1—C2—C3—C4	−179.18 (11)	C7—C6—C5—O3	−179.57 (10)
C2—C3—C4—C5	0.20 (19)	C7—C6—C5—C4	0.22 (18)
C8—O2—C7—C6	2.28 (16)	C3—C4—C5—O3	179.19 (11)
C8—O2—C7—C2	−177.39 (10)	C3—C4—C5—C6	−0.58 (18)
C5—C6—C7—O2	−179.13 (10)	C3—C2—C1—O1	−2.48 (19)
C5—C6—C7—C2	0.53 (17)	C7—C2—C1—O1	177.83 (12)
C3—C2—C7—O2	178.80 (10)	C5—O3—C11—C12	178.25 (10)
C1—C2—C7—O2	−1.51 (16)	C13—C12—C11—O3	166 (6)
C3—C2—C7—C6	−0.89 (16)	C7—O2—C8—C9	−178.20 (10)
C1—C2—C7—C6	178.81 (11)	C10—C9—C8—O2	−177 (100)
C11—O3—C5—C6	−175.24 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.48	3.3616 (14)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.48	3.3616 (14)	159

Symmetry code: (i) .