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In the mol­ecule of the title compound, C10H8N2O, the ring is nearly planar, but the molecule as a whole is not planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037998/hk2119sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037998/hk2119Isup2.hkl
Contains datablock I

CCDC reference: 627792

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.057
  • wR factor = 0.193
  • Data-to-parameter ratio = 20.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.34
Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C7 .. 5.94 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C6 ... 1.42 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-(2,6-Dimethyl-4H-pyran-4-ylidene)malononitrile top
Crystal data top
C10H8N2OZ = 2
Mr = 172.18F(000) = 180
Triclinic, P1Dx = 1.271 Mg m3
Hall symbol: -P 1Melting point: 471 K
a = 7.249 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.871 (1) ÅCell parameters from 659 reflections
c = 9.0350 (15) Åθ = 2.9–24.9°
α = 72.996 (8)°µ = 0.09 mm1
β = 74.362 (8)°T = 294 K
γ = 68.159 (7)°Block, colourless
V = 450.02 (11) Å30.30 × 0.22 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1525 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 26.5°, θmin = 2.4°
φ and ω scansh = 69
4494 measured reflectionsk = 99
2497 independent reflectionsl = 1110
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.193 w = 1/[σ2(Fo2) + (0.1026P)2 + 0.0324P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.004
2497 reflectionsΔρmax = 0.21 e Å3
122 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.14 (2)
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
O10.3105 (3)0.9518 (2)0.21788 (17)0.0518 (6)
N10.2270 (5)0.7865 (4)0.9104 (3)0.0873 (10)
N20.1428 (4)1.3879 (4)0.6945 (3)0.0711 (8)
C10.3648 (5)0.6282 (4)0.3026 (3)0.0634 (8)
H1A0.28140.64310.23020.095*
H1B0.34080.53530.39510.095*
H1C0.50440.58890.25360.095*
C20.3152 (4)0.8083 (4)0.3469 (3)0.0474 (7)
C30.2786 (4)0.8381 (4)0.4925 (3)0.0459 (7)
H30.28050.73800.57850.055*
C40.2373 (3)1.0188 (3)0.5175 (3)0.0413 (6)
C50.2051 (4)1.0550 (4)0.6664 (3)0.0475 (7)
C60.2159 (5)0.9074 (4)0.8029 (3)0.0600 (8)
C70.1707 (4)1.2369 (4)0.6845 (3)0.0532 (7)
C80.2243 (4)1.1663 (4)0.3797 (3)0.0465 (7)
H80.18981.28940.38910.056*
C90.2614 (4)1.1290 (4)0.2370 (3)0.0474 (7)
C100.2532 (5)1.2673 (4)0.0846 (3)0.0669 (9)
H10A0.14961.26680.03740.100*
H10B0.38131.23440.01550.100*
H10C0.22351.39000.10220.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0642 (13)0.0477 (11)0.0428 (10)0.0225 (10)0.0077 (9)0.0040 (8)
N10.114 (3)0.091 (2)0.0583 (16)0.0443 (19)0.0314 (16)0.0126 (15)
N20.086 (2)0.0619 (17)0.0655 (16)0.0188 (16)0.0159 (14)0.0173 (13)
C10.072 (2)0.0543 (18)0.0690 (18)0.0273 (16)0.0144 (16)0.0095 (14)
C20.0430 (16)0.0440 (16)0.0538 (16)0.0185 (13)0.0091 (13)0.0020 (13)
C30.0417 (16)0.0448 (15)0.0465 (14)0.0170 (13)0.0090 (12)0.0024 (12)
C40.0299 (14)0.0475 (16)0.0432 (14)0.0136 (12)0.0078 (11)0.0022 (11)
C50.0443 (16)0.0518 (17)0.0432 (14)0.0151 (14)0.0094 (12)0.0043 (12)
C60.064 (2)0.074 (2)0.0437 (15)0.0272 (17)0.0169 (15)0.0019 (15)
C70.0499 (18)0.067 (2)0.0399 (15)0.0200 (16)0.0083 (13)0.0055 (14)
C80.0457 (16)0.0443 (15)0.0450 (15)0.0142 (13)0.0082 (12)0.0035 (12)
C90.0442 (16)0.0461 (16)0.0488 (15)0.0183 (13)0.0075 (12)0.0013 (12)
C100.089 (2)0.0611 (19)0.0425 (15)0.0287 (18)0.0111 (15)0.0053 (13)
Geometric parameters (Å, º) top
O1—C91.356 (3)C4—C51.397 (3)
O1—C21.363 (3)C4—C81.430 (3)
N1—C61.140 (3)C5—C71.410 (4)
N2—C71.156 (3)C5—C61.422 (4)
C1—C21.474 (4)C8—C91.340 (3)
C1—H1A0.9600C8—H80.9300
C1—H1B0.9600C9—C101.485 (3)
C1—H1C0.9600C10—H10A0.9600
C2—C31.342 (3)C10—H10B0.9600
C3—C41.414 (3)C10—H10C0.9600
C3—H30.9300
C9—O1—C2119.5 (2)C4—C5—C6120.7 (2)
C2—C1—H1A109.5C7—C5—C6118.3 (2)
C2—C1—H1B109.5N1—C6—C5178.6 (4)
H1A—C1—H1B109.5N2—C7—C5177.9 (3)
C2—C1—H1C109.5C9—C8—C4120.7 (2)
H1A—C1—H1C109.5C9—C8—H8119.7
H1B—C1—H1C109.5C4—C8—H8119.7
C3—C2—O1121.2 (2)C8—C9—O1121.7 (2)
C3—C2—C1127.3 (2)C8—C9—C10126.5 (3)
O1—C2—C1111.5 (2)O1—C9—C10111.8 (2)
C2—C3—C4121.3 (2)C9—C10—H10A109.5
C2—C3—H3119.4C9—C10—H10B109.5
C4—C3—H3119.4H10A—C10—H10B109.5
C5—C4—C3123.2 (2)C9—C10—H10C109.5
C5—C4—C8121.3 (2)H10A—C10—H10C109.5
C3—C4—C8115.6 (2)H10B—C10—H10C109.5
C4—C5—C7120.9 (2)
C9—O1—C2—C32.2 (4)C3—C4—C5—C61.1 (4)
C9—O1—C2—C1178.1 (2)C8—C4—C5—C6179.2 (3)
O1—C2—C3—C41.1 (4)C5—C4—C8—C9178.0 (2)
C1—C2—C3—C4178.5 (3)C3—C4—C8—C93.7 (4)
C2—C3—C4—C5177.8 (2)C4—C8—C9—O10.6 (4)
C2—C3—C4—C84.0 (4)C4—C8—C9—C10179.9 (2)
C3—C4—C5—C7178.0 (2)C2—O1—C9—C82.5 (4)
C8—C4—C5—C73.9 (4)C2—O1—C9—C10176.9 (2)
 

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