In the title compound, C
11H
9N
3O, the three cyano groups, the C atom of one of the three methyl groups and the dihydrofuran ring atoms lie on a crystallographic mirror plane. A weak C—H
N interaction results in one-dimensional chains.
Supporting information
CCDC reference: 277255
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.065
- wR factor = 0.213
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.148
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.15
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C8 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C6 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C7 ... 1.42 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Crystal data top
C11H9N3O | F(000) = 208 |
Mr = 199.21 | Dx = 1.203 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb | Cell parameters from 738 reflections |
a = 9.485 (2) Å | θ = 2.5–22.4° |
b = 6.8022 (16) Å | µ = 0.08 mm−1 |
c = 9.681 (2) Å | T = 298 K |
β = 118.263 (3)° | Block, colourless |
V = 550.1 (2) Å3 | 0.40 × 0.36 × 0.26 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1182 independent reflections |
Radiation source: fine-focus sealed tube | 804 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.148 |
ω scans | θmax = 26.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→7 |
Tmin = 0.968, Tmax = 0.979 | k = −7→8 |
3143 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.213 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.128P)2] where P = (Fo2 + 2Fc2)/3 |
1182 reflections | (Δ/σ)max < 0.001 |
88 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.9773 (2) | 0.2500 | 0.1568 (2) | 0.0673 (7) | |
N1 | 0.5580 (5) | 0.2500 | −0.0750 (4) | 0.1362 (18) | |
N2 | 0.6580 (4) | 0.2500 | 0.4133 (4) | 0.0980 (11) | |
N3 | 1.0602 (4) | 0.2500 | 0.6821 (3) | 0.0862 (10) | |
C1 | 0.9260 (3) | 0.2500 | 0.2634 (3) | 0.0545 (7) | |
C2 | 1.0632 (3) | 0.2500 | 0.4180 (3) | 0.0524 (7) | |
C3 | 1.1980 (3) | 0.2500 | 0.4049 (3) | 0.0542 (8) | |
C4 | 1.1545 (3) | 0.2500 | 0.2346 (3) | 0.0614 (8) | |
C5 | 0.7666 (3) | 0.2500 | 0.2172 (3) | 0.0609 (8) | |
C6 | 0.6514 (4) | 0.2500 | 0.0544 (4) | 0.0860 (11) | |
C7 | 0.7072 (4) | 0.2500 | 0.3268 (4) | 0.0686 (9) | |
C8 | 1.0582 (4) | 0.2500 | 0.5644 (3) | 0.0609 (8) | |
C9 | 1.3652 (3) | 0.2500 | 0.5304 (4) | 0.0711 (9) | |
H9A | 1.3674 | 0.2500 | 0.6305 | 0.107* | |
H9B | 1.4186 | 0.3652 | 0.5212 | 0.107* | 0.50 |
0H9C | 1.4186 | 0.1348 | 0.5212 | 0.107* | 0.50 |
C10 | 1.2054 (3) | 0.0643 (4) | 0.1858 (3) | 0.0896 (9) | |
H10A | 1.1690 | −0.0476 | 0.2206 | 0.134* | |
H10B | 1.3200 | 0.0611 | 0.2321 | 0.134* | |
H10C | 1.1595 | 0.0611 | 0.0737 | 0.134* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0437 (11) | 0.0985 (16) | 0.0501 (11) | 0.000 | 0.0143 (9) | 0.000 |
N1 | 0.067 (2) | 0.237 (5) | 0.074 (2) | 0.000 | 0.0083 (18) | 0.000 |
N2 | 0.080 (2) | 0.124 (3) | 0.104 (2) | 0.000 | 0.056 (2) | 0.000 |
N3 | 0.096 (2) | 0.101 (2) | 0.0635 (17) | 0.000 | 0.0396 (17) | 0.000 |
C1 | 0.0504 (16) | 0.0544 (16) | 0.0525 (14) | 0.000 | 0.0193 (12) | 0.000 |
C2 | 0.0526 (16) | 0.0427 (14) | 0.0530 (15) | 0.000 | 0.0177 (12) | 0.000 |
C3 | 0.0469 (15) | 0.0486 (15) | 0.0567 (15) | 0.000 | 0.0160 (12) | 0.000 |
C4 | 0.0398 (14) | 0.082 (2) | 0.0536 (15) | 0.000 | 0.0149 (12) | 0.000 |
C5 | 0.0459 (16) | 0.0701 (18) | 0.0586 (16) | 0.000 | 0.0182 (13) | 0.000 |
C6 | 0.0483 (18) | 0.126 (3) | 0.070 (2) | 0.000 | 0.0177 (16) | 0.000 |
C7 | 0.0531 (18) | 0.075 (2) | 0.077 (2) | 0.000 | 0.0298 (17) | 0.000 |
C8 | 0.0608 (18) | 0.0535 (16) | 0.0585 (17) | 0.000 | 0.0201 (14) | 0.000 |
C9 | 0.0484 (17) | 0.084 (2) | 0.0632 (18) | 0.000 | 0.0117 (14) | 0.000 |
C10 | 0.0652 (15) | 0.114 (2) | 0.0817 (17) | 0.0044 (14) | 0.0285 (13) | −0.0272 (14) |
Geometric parameters (Å, º) top
C1—O1 | 1.333 (4) | C4—C10 | 1.506 (3) |
C4—O1 | 1.481 (3) | C4—C10i | 1.506 (3) |
C6—N1 | 1.142 (5) | C5—C7 | 1.417 (5) |
C7—N2 | 1.136 (4) | C5—C6 | 1.431 (4) |
C8—N3 | 1.130 (4) | C9—H9A | 0.9600 |
C1—C5 | 1.359 (4) | C9—H9B | 0.9600 |
C1—C2 | 1.445 (4) | C9—0H9C | 0.9600 |
C2—C3 | 1.343 (4) | C10—H10A | 0.9600 |
C2—C8 | 1.441 (4) | C10—H10B | 0.9600 |
C3—C9 | 1.472 (4) | C10—H10C | 0.9600 |
C3—C4 | 1.498 (4) | | |
| | | |
C1—O1—C4 | 110.4 (2) | C1—C5—C6 | 120.8 (3) |
O1—C1—C5 | 120.2 (3) | C7—C5—C6 | 117.3 (3) |
O1—C1—C2 | 108.8 (2) | N1—C6—C5 | 179.1 (4) |
C5—C1—C2 | 131.0 (3) | N2—C7—C5 | 179.3 (3) |
C3—C2—C8 | 124.7 (3) | N3—C8—C2 | 177.5 (3) |
C3—C2—C1 | 109.4 (3) | C3—C9—H9A | 109.5 |
C8—C2—C1 | 125.9 (3) | C3—C9—H9B | 109.5 |
C2—C3—C9 | 128.6 (3) | H9A—C9—H9B | 109.5 |
C2—C3—C4 | 109.0 (2) | C3—C9—0H9C | 109.5 |
C9—C3—C4 | 122.4 (3) | H9A—C9—0H9C | 109.5 |
O1—C4—C3 | 102.4 (2) | H9B—C9—0H9C | 109.5 |
O1—C4—C10 | 107.18 (15) | C4—C10—H10A | 109.5 |
C3—C4—C10 | 112.53 (16) | C4—C10—H10B | 109.5 |
O1—C4—C10i | 107.18 (15) | H10A—C10—H10B | 109.5 |
C3—C4—C10i | 112.53 (16) | C4—C10—H10C | 109.5 |
C10—C4—C10i | 114.0 (3) | H10A—C10—H10C | 109.5 |
C1—C5—C7 | 121.9 (3) | H10B—C10—H10C | 109.5 |
| | | |
C4—O1—C1—C5 | 180.0 | C1—O1—C4—C10i | −118.59 (19) |
C4—O1—C1—C2 | 0.0 | C2—C3—C4—O1 | 0.0 |
O1—C1—C2—C3 | 0.0 | C9—C3—C4—O1 | 180.0 |
C5—C1—C2—C3 | 180.0 | C2—C3—C4—C10 | −114.74 (19) |
O1—C1—C2—C8 | 180.0 | C9—C3—C4—C10 | 65.26 (19) |
C5—C1—C2—C8 | 0.0 | C2—C3—C4—C10i | 114.74 (19) |
C8—C2—C3—C9 | 0.0 | C9—C3—C4—C10i | −65.26 (19) |
C1—C2—C3—C9 | 180.0 | O1—C1—C5—C7 | 180.0 |
C8—C2—C3—C4 | 180.0 | C2—C1—C5—C7 | 0.0 |
C1—C2—C3—C4 | 0.0 | O1—C1—C5—C6 | 0.0 |
C1—O1—C4—C3 | 0.0 | C2—C1—C5—C6 | 180.0 |
C1—O1—C4—C10 | 118.59 (19) | | |
Symmetry code: (i) x, −y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···N1ii | 0.96 | 2.55 | 3.365 (5) | 143 |
Symmetry code: (ii) x+1, y, z+1. |