3-Meth­oxy-4-(prop-2-yn-1-yl­oxy)benzaldehyde

In the title compound, C₁₁H₁₀O₃, the prop-2-yn-1-yl group is inclined to the benzene ring by 69 (7)°. In the crystal, mol­ecules are linked by a pair of C—H...O hydrogen bonds, forming inversion dimers with an R₂²(12) ring motif. The dimers are linked by a second C—H...O hydrogen bond, forming sheets parallel to the (102) plane. The sheets stack along the c-axis direction with a separation of ca 3.4 Å.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

3-Methoxy-4-(prop-2-yn-1-yloxy)benzaldehyde

Crystal data

C11H10O3	F(000) = 400
Mr = 190.19	Dx = 1.313 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4115 reflections
a = 11.8560 (6) Å	θ = 2.4–28.4°
b = 11.8836 (6) Å	µ = 0.10 mm^−1
c = 6.8348 (4) Å	T = 296 K
β = 92.044 (1)°	Block, brown
V = 962.36 (9) Å^3	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer	1896 independent reflections
Radiation source: fine-focus sealed tube	1528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω and φ scan	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.961, Tmax = 0.980	k = −14→14
10764 measured reflections	l = −8→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0353P)^2 + 0.2349P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1896 reflections	Δρmax = 0.15 e Å^−3
129 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0104 (19)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.25864 (14)	0.36251 (15)	−0.2945 (3)	0.0699 (5)
H1	0.2947	0.3419	−0.4077	0.084*
C2	0.21334 (12)	0.38838 (13)	−0.1523 (3)	0.0539 (4)
C3	0.15648 (13)	0.41756 (12)	0.0269 (2)	0.0547 (4)
H3A	0.0865	0.3755	0.0317	0.066*
H3B	0.2039	0.3955	0.1390	0.066*
C4	0.22014 (11)	0.60814 (11)	0.06716 (18)	0.0383 (3)
C5	0.33237 (11)	0.57799 (12)	0.09667 (19)	0.0433 (3)
H5	0.3527	0.5024	0.0997	0.052*
C6	0.41399 (11)	0.65991 (12)	0.12150 (19)	0.0445 (3)
H6	0.4893	0.6394	0.1408	0.053*
C7	0.38435 (11)	0.77230 (11)	0.11782 (18)	0.0416 (3)
C8	0.27149 (11)	0.80274 (11)	0.09066 (18)	0.0403 (3)
H8	0.2516	0.8784	0.0902	0.048*
C9	0.18929 (11)	0.72245 (11)	0.06453 (18)	0.0379 (3)
C10	0.04141 (14)	0.85726 (13)	0.0341 (3)	0.0610 (4)
H10A	0.0620	0.8914	0.1576	0.091*
H10B	−0.0390	0.8607	0.0131	0.091*
H10C	0.0773	0.8969	−0.0691	0.091*
C11	0.46886 (14)	0.86149 (14)	0.1404 (2)	0.0579 (4)
H11	0.4424	0.9352	0.1418	0.069*
O1	0.13206 (8)	0.53520 (8)	0.03999 (15)	0.0511 (3)
O2	0.07696 (8)	0.74270 (8)	0.03513 (15)	0.0518 (3)
O3	0.56883 (10)	0.84848 (12)	0.1572 (2)	0.0815 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0562 (10)	0.0683 (12)	0.0853 (13)	−0.0013 (8)	0.0054 (9)	−0.0240 (10)
C2	0.0445 (8)	0.0405 (8)	0.0762 (11)	−0.0023 (6)	−0.0035 (7)	−0.0097 (7)
C3	0.0559 (9)	0.0348 (8)	0.0739 (10)	−0.0050 (6)	0.0070 (8)	−0.0006 (7)
C4	0.0421 (7)	0.0379 (7)	0.0349 (6)	−0.0026 (6)	0.0015 (5)	−0.0017 (5)
C5	0.0475 (8)	0.0389 (7)	0.0431 (7)	0.0049 (6)	−0.0024 (6)	−0.0015 (6)
C6	0.0402 (7)	0.0542 (9)	0.0390 (7)	0.0019 (6)	−0.0016 (5)	−0.0036 (6)
C7	0.0464 (8)	0.0466 (8)	0.0321 (6)	−0.0061 (6)	0.0052 (5)	−0.0040 (6)
C8	0.0513 (8)	0.0358 (7)	0.0341 (6)	−0.0002 (6)	0.0054 (5)	−0.0016 (5)
C9	0.0410 (7)	0.0407 (7)	0.0320 (6)	0.0030 (6)	0.0020 (5)	−0.0019 (5)
C10	0.0585 (9)	0.0513 (9)	0.0729 (11)	0.0178 (8)	−0.0019 (8)	−0.0047 (8)
C11	0.0568 (10)	0.0608 (10)	0.0568 (10)	−0.0121 (8)	0.0107 (7)	−0.0090 (7)
O1	0.0439 (6)	0.0375 (5)	0.0720 (7)	−0.0023 (4)	0.0033 (5)	−0.0072 (5)
O2	0.0434 (6)	0.0431 (6)	0.0684 (7)	0.0068 (4)	−0.0034 (5)	−0.0062 (5)
O3	0.0540 (8)	0.0867 (10)	0.1042 (10)	−0.0200 (7)	0.0096 (7)	−0.0199 (8)

Geometric parameters (Å, º)

C1—C2	1.168 (2)	C6—H6	0.9300
C1—H1	0.9300	C7—C8	1.3921 (19)
C2—C3	1.460 (2)	C7—C11	1.463 (2)
C3—O1	1.4311 (17)	C8—C9	1.3711 (18)
C3—H3A	0.9700	C8—H8	0.9300
C3—H3B	0.9700	C9—O2	1.3612 (16)
C4—O1	1.3647 (16)	C10—O2	1.4251 (17)
C4—C5	1.3858 (18)	C10—H10A	0.9600
C4—C9	1.4068 (18)	C10—H10B	0.9600
C5—C6	1.3789 (19)	C10—H10C	0.9600
C5—H5	0.9300	C11—O3	1.1968 (19)
C6—C7	1.3812 (19)	C11—H11	0.9300
C2—C1—H1	180.0	C8—C7—C11	118.51 (13)
C1—C2—C3	178.47 (18)	C9—C8—C7	120.80 (12)
O1—C3—C2	112.64 (13)	C9—C8—H8	119.6
O1—C3—H3A	109.1	C7—C8—H8	119.6
C2—C3—H3A	109.1	O2—C9—C8	125.69 (12)
O1—C3—H3B	109.1	O2—C9—C4	115.16 (11)
C2—C3—H3B	109.1	C8—C9—C4	119.15 (12)
H3A—C3—H3B	107.8	O2—C10—H10A	109.5
O1—C4—C5	125.57 (12)	O2—C10—H10B	109.5
O1—C4—C9	114.47 (11)	H10A—C10—H10B	109.5
C5—C4—C9	119.96 (12)	O2—C10—H10C	109.5
C6—C5—C4	120.10 (13)	H10A—C10—H10C	109.5
C6—C5—H5	120.0	H10B—C10—H10C	109.5
C4—C5—H5	120.0	O3—C11—C7	126.07 (16)
C5—C6—C7	120.23 (13)	O3—C11—H11	117.0
C5—C6—H6	119.9	C7—C11—H11	117.0
C7—C6—H6	119.9	C4—O1—C3	118.26 (11)
C6—C7—C8	119.76 (12)	C9—O2—C10	117.21 (11)
C6—C7—C11	121.73 (13)
C1—C2—C3—O1	−174 (100)	C5—C4—C9—O2	−179.79 (11)
O1—C4—C5—C6	179.69 (12)	O1—C4—C9—C8	179.94 (11)
C9—C4—C5—C6	−0.66 (19)	C5—C4—C9—C8	0.26 (18)
C4—C5—C6—C7	0.2 (2)	C6—C7—C11—O3	2.6 (2)
C5—C6—C7—C8	0.6 (2)	C8—C7—C11—O3	−176.98 (15)
C5—C6—C7—C11	−178.98 (12)	C5—C4—O1—C3	−4.62 (19)
C6—C7—C8—C9	−0.97 (19)	C9—C4—O1—C3	175.72 (12)
C11—C7—C8—C9	178.59 (12)	C2—C3—O1—C4	−69.00 (17)
C7—C8—C9—O2	−179.39 (11)	C8—C9—O2—C10	−0.92 (19)
C7—C8—C9—C4	0.55 (18)	C4—C9—O2—C10	179.13 (12)
O1—C4—C9—O2	−0.11 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2^i	0.97	2.42	3.374 (2)	166
C1—H1···O3^ii	0.93	2.39	3.274 (2)	158

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