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The title compound, C9H6O2, contains two moderate C—H...O hydrogen bonds. That involving the terminal alkyne gives rise to chains along the b axis. The other hydrogen bond occurs over a centre of symmetry, leading to dimers. The combination of the two interactions gives rise to rings, each comprising six mol­ecules, which are part of infinite sheets in the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100019909/gd1130sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100019909/gd1130Isup2.hkl
Contains datablock I

CCDC reference: 163906

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and PLATON.

4-Ethynyl-1,2-methylenedioxybenzene top
Crystal data top
C9H6O2Dx = 1.411 Mg m3
Mr = 146.14Melting point: 260 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.318 (3) ÅCell parameters from 40 reflections
b = 15.867 (10) Åθ = 10.2–12.6°
c = 7.571 (4) ŵ = 0.10 mm1
β = 115.03 (3)°T = 150 K
V = 687.7 (7) Å3Needle, pale yellow
Z = 40.19 × 0.11 × 0.08 mm
F(000) = 304
Data collection top
Stoe Stadi-4 four-circle
diffractometer
Rint = 0.196
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 2.6°
Planar graphite monochromatorh = 77
ω/θ scansk = 1919
5424 measured reflectionsl = 99
1356 independent reflections3 standard reflections every 60 min
729 reflections with I > 2σ(I) intensity decay: 9.6%
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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + 1.647P]
where P = (Fo2 + 2Fc2)/3
1356 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.35 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 > 2σ(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
C10.5011 (8)0.6364 (3)0.3161 (7)0.0200 (10)
C20.5051 (8)0.5596 (3)0.2221 (7)0.0217 (11)
H20.61270.55020.16660.026*
C30.3461 (8)0.4997 (3)0.2152 (7)0.0207 (11)
C40.1872 (8)0.5128 (3)0.2944 (7)0.0202 (10)
C50.1790 (9)0.5859 (3)0.3864 (8)0.0264 (12)
H50.06950.59410.44040.032*
C60.3405 (8)0.6479 (3)0.3966 (7)0.0246 (12)
H60.34150.69960.46020.029*
C70.6634 (8)0.7028 (3)0.3289 (7)0.0218 (11)
C80.7933 (9)0.7584 (3)0.3412 (7)0.0287 (12)
H80.89770.80310.35110.034*
O90.3145 (6)0.4212 (2)0.1324 (5)0.0275 (9)
C100.1292 (8)0.3822 (3)0.1671 (8)0.0294 (12)
H10A0.00090.36480.04210.035*
H10B0.18850.33160.24990.035*
O110.0461 (6)0.4430 (2)0.2634 (5)0.0296 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.019 (2)0.021 (3)0.020 (3)0.003 (2)0.008 (2)0.003 (2)
C20.026 (3)0.026 (3)0.017 (3)0.000 (2)0.014 (2)0.001 (2)
C30.022 (2)0.019 (3)0.023 (3)0.001 (2)0.012 (2)0.003 (2)
C40.021 (2)0.022 (3)0.018 (3)0.002 (2)0.008 (2)0.005 (2)
C50.027 (3)0.028 (3)0.032 (3)0.007 (2)0.020 (2)0.004 (2)
C60.027 (3)0.022 (3)0.026 (3)0.007 (2)0.013 (2)0.003 (2)
C70.020 (2)0.022 (3)0.023 (3)0.004 (2)0.009 (2)0.001 (2)
C80.027 (3)0.029 (3)0.032 (3)0.000 (2)0.014 (2)0.001 (3)
O90.035 (2)0.0222 (18)0.034 (2)0.0075 (16)0.0227 (18)0.0065 (16)
C100.031 (3)0.027 (3)0.034 (3)0.007 (2)0.017 (3)0.004 (2)
O110.0311 (19)0.032 (2)0.034 (2)0.0039 (17)0.0217 (18)0.0023 (17)
Geometric parameters (Å, º) top
C1—C61.399 (6)C4—C51.365 (7)
C1—C21.416 (6)C4—O111.378 (6)
C1—C71.444 (6)C5—C61.396 (7)
C2—C31.368 (6)C7—C81.182 (7)
C3—O91.371 (5)O9—C101.443 (5)
C3—C41.385 (6)C10—O111.435 (6)
C6—C1—C2120.1 (4)C5—C4—C3122.6 (4)
C6—C1—C7120.0 (4)O11—C4—C3109.9 (4)
C2—C1—C7119.9 (4)C4—C5—C6116.3 (4)
C3—C2—C1116.6 (4)C5—C6—C1122.1 (5)
C2—C3—O9127.7 (4)C8—C7—C1178.3 (5)
C2—C3—C4122.3 (4)C3—O9—C10106.2 (3)
O9—C3—C4110.0 (4)O11—C10—O9107.7 (4)
C5—C4—O11127.5 (4)C4—O11—C10106.1 (3)
C6—C1—C2—C30.2 (7)C4—C5—C6—C10.5 (7)
C7—C1—C2—C3179.9 (4)C2—C1—C6—C50.6 (7)
C1—C2—C3—O9179.6 (5)C7—C1—C6—C5179.4 (5)
C1—C2—C3—C40.4 (7)C2—C3—O9—C10179.0 (5)
C2—C3—C4—C50.6 (7)C4—C3—O9—C101.7 (5)
O9—C3—C4—C5180.0 (5)C3—O9—C10—O113.2 (5)
C2—C3—C4—O11178.8 (5)C5—C4—O11—C10178.1 (5)
O9—C3—C4—O110.5 (5)C3—C4—O11—C102.5 (5)
O11—C4—C5—C6179.2 (5)O9—C10—O11—C43.5 (5)
C3—C4—C5—C60.1 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O9i0.952.583.526 (7)178
C2—H2···O9ii0.952.533.344 (7)143
C5—H5···O11iii0.952.703.529 (7)146
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1, y+1, z; (iii) x, y+1, z+1.
 

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