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In the title mol­ecule, C10H8O2, all bond lengths and angles are normal. In the propyne group, the C atoms are almost collinear, making a C—C—C angle of 177.71 (18)°. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042127/cv2136sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042127/cv2136Isup2.hkl
Contains datablock I

CCDC reference: 627475

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.131
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-(prop-2-ynyloxy)benzaldehyde top
Crystal data top
C10H8O2Z = 2
Mr = 160.16F(000) = 168
Triclinic, P1Dx = 1.298 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.4758 (16) ÅCell parameters from 2774 reflections
b = 10.043 (4) Åθ = 2.4–22.6°
c = 10.057 (4) ŵ = 0.09 mm1
α = 66.980 (4)°T = 298 K
β = 80.218 (5)°Block, colourless
γ = 87.632 (5)°0.50 × 0.36 × 0.34 mm
V = 409.9 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1416 independent reflections
Radiation source: fine-focus sealed tube1158 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 55
Tmin = 0.956, Tmax = 0.970k = 1111
2066 measured reflectionsl = 1110
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0739P)2 + 0.0349P]
where P = (Fo2 + 2Fc2)/3
1416 reflections(Δ/σ)max < 0.001
113 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
O10.5167 (3)0.38679 (13)0.76502 (15)0.0747 (5)
O20.1836 (3)0.69206 (12)0.90225 (12)0.0601 (4)
C10.2338 (4)0.59947 (16)0.71858 (18)0.0471 (4)
C20.1718 (4)0.60703 (19)0.5850 (2)0.0567 (5)
H2A0.24970.53760.54970.068*
C30.0004 (5)0.7136 (2)0.5043 (2)0.0627 (5)
H3A0.03700.71760.41450.075*
C40.1195 (4)0.8153 (2)0.5576 (2)0.0625 (5)
H4A0.23980.88720.50390.075*
C50.0630 (4)0.81210 (18)0.6892 (2)0.0573 (5)
H5A0.14330.88190.72350.069*
C60.1139 (4)0.70445 (16)0.77052 (17)0.0477 (4)
C70.4233 (4)0.48508 (18)0.7999 (2)0.0586 (5)
H7A0.47580.48800.88430.070*
C80.0804 (5)0.80090 (19)0.95746 (19)0.0594 (5)
H8A0.10670.76751.05910.071*
H8B0.13460.81420.95430.071*
C90.2414 (4)0.9400 (2)0.87474 (19)0.0553 (5)
C100.3692 (5)1.0517 (3)0.8132 (2)0.0691 (6)
H80.473 (6)1.139 (3)0.767 (3)0.107 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0939 (11)0.0513 (8)0.0866 (10)0.0146 (7)0.0101 (8)0.0383 (7)
O20.0838 (10)0.0474 (7)0.0578 (7)0.0133 (6)0.0136 (6)0.0300 (6)
C10.0473 (10)0.0389 (9)0.0560 (10)0.0086 (7)0.0024 (7)0.0231 (7)
C20.0587 (11)0.0524 (10)0.0652 (11)0.0080 (8)0.0006 (9)0.0332 (9)
C30.0686 (13)0.0638 (12)0.0600 (11)0.0095 (10)0.0112 (9)0.0275 (9)
C40.0641 (12)0.0526 (11)0.0710 (12)0.0014 (9)0.0189 (9)0.0209 (9)
C50.0609 (11)0.0452 (10)0.0698 (11)0.0034 (8)0.0074 (9)0.0286 (8)
C60.0524 (10)0.0396 (9)0.0517 (9)0.0062 (7)0.0004 (7)0.0212 (7)
C70.0711 (13)0.0451 (10)0.0641 (11)0.0014 (8)0.0045 (9)0.0286 (9)
C80.0759 (13)0.0526 (10)0.0557 (10)0.0086 (9)0.0032 (9)0.0315 (8)
C90.0656 (12)0.0521 (11)0.0591 (10)0.0107 (9)0.0107 (9)0.0341 (9)
C100.0775 (15)0.0609 (14)0.0784 (14)0.0005 (11)0.0104 (11)0.0380 (11)
Geometric parameters (Å, º) top
O1—C71.208 (2)C4—C51.377 (2)
O2—C61.370 (2)C4—H4A0.9300
O2—C81.4362 (19)C5—C61.386 (3)
C1—C21.390 (3)C5—H5A0.9300
C1—C61.400 (2)C7—H7A0.9300
C1—C71.459 (3)C8—C91.461 (3)
C2—C31.365 (3)C8—H8A0.9700
C2—H2A0.9300C8—H8B0.9700
C3—C41.379 (3)C9—C101.165 (3)
C3—H3A0.9300C10—H80.92 (3)
C6—O2—C8118.43 (13)C6—C5—H5A120.1
C2—C1—C6118.43 (16)O2—C6—C5124.23 (15)
C2—C1—C7119.84 (15)O2—C6—C1115.88 (15)
C6—C1—C7121.72 (16)C5—C6—C1119.89 (16)
C3—C2—C1121.75 (17)O1—C7—C1124.47 (18)
C3—C2—H2A119.1O1—C7—H7A117.8
C1—C2—H2A119.1C1—C7—H7A117.8
C2—C3—C4119.11 (17)O2—C8—C9113.00 (14)
C2—C3—H3A120.4O2—C8—H8A109.0
C4—C3—H3A120.4C9—C8—H8A109.0
C5—C4—C3121.04 (18)O2—C8—H8B109.0
C5—C4—H4A119.5C9—C8—H8B109.0
C3—C4—H4A119.5H8A—C8—H8B107.8
C4—C5—C6119.77 (17)C10—C9—C8177.71 (18)
C4—C5—H5A120.1C9—C10—H8178.4 (17)
C6—C1—C2—C30.2 (3)C4—C5—C6—C10.1 (3)
C7—C1—C2—C3178.95 (15)C2—C1—C6—O2179.69 (14)
C1—C2—C3—C40.9 (3)C7—C1—C6—O20.5 (2)
C2—C3—C4—C51.1 (3)C2—C1—C6—C50.3 (2)
C3—C4—C5—C60.6 (3)C7—C1—C6—C5179.44 (16)
C8—O2—C6—C53.2 (2)C2—C1—C7—O15.7 (3)
C8—O2—C6—C1176.79 (14)C6—C1—C7—O1175.12 (16)
C4—C5—C6—O2179.85 (15)C6—O2—C8—C971.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H8···O1i0.92 (3)2.50 (3)3.286 (3)144 (2)
Symmetry code: (i) x, y+1, z.
 

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