2-(1-Methyl-2-oxoindolin-3-yl-idene)malono-nitrile.

The title mol-ecule, C12H7N3O, is almost planar, with an r.m.s. deviation of 0.026 Å. No directional interactions could be detected in the crystal.

Related literature

For background literature, see: Demchuk et al. (2011 ▶). For the crystal structure of a related compound, see: Spencer et al. (2010) ▶.

Experimental

Crystal data

C12H7N3O

M = 209.21

Monoclinic,

a = 6.9720 (14) Å

b = 9.929 (2) Å

c = 15.084 (3) Å

β = 100.25 (3)°

V = 1027.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.973, T max = 0.991

2056 measured reflections

1896 independent reflections

1278 reflections with I > 2σ(I)

R int = 0.081

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.176

S = 1.00

1896 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016012/pv2634sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016012/pv2634Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016012/pv2634Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H7N3O	F(000) = 432
Mr = 209.21	Dx = 1.352 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 6.9720 (14) Å	θ = 9–13°
b = 9.929 (2) Å	µ = 0.09 mm−1
c = 15.084 (3) Å	T = 293 K
β = 100.25 (3)°	Block, yellow
V = 1027.5 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1278 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
Graphite monochromator	θmax = 25.4°, θmin = 2.5°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.973, Tmax = 0.991	l = −18→17
2056 measured reflections	3 standard reflections every 200 reflections
1896 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.1P)2 + 0.150P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1896 reflections	Δρmax = 0.18 e Å−3
146 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.082 (11)

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.

	x	y	z	Uiso*/Ueq
O	0.0898 (3)	0.2173 (2)	0.80717 (13)	0.0706 (7)
C1	0.0975 (4)	−0.0799 (3)	0.83219 (16)	0.0473 (7)
N1	0.1159 (4)	−0.3343 (3)	0.86555 (18)	0.0819 (9)
C2	0.1095 (4)	−0.2216 (3)	0.85071 (18)	0.0553 (7)
N2	−0.0627 (5)	−0.0331 (3)	0.66758 (18)	0.0853 (9)
C3	0.0117 (4)	−0.0467 (3)	0.74109 (18)	0.0583 (8)
N3	0.2174 (3)	0.2233 (2)	0.95933 (14)	0.0526 (6)
C4	0.1582 (3)	0.0124 (2)	0.89713 (16)	0.0439 (6)
C5	0.1483 (4)	0.1621 (3)	0.87912 (17)	0.0505 (7)
C6	0.2761 (3)	0.1273 (2)	1.02696 (16)	0.0452 (6)
C7	0.3584 (4)	0.1494 (3)	1.11602 (17)	0.0535 (7)
H7A	0.3832	0.2361	1.1385	0.064*
C8	0.4027 (4)	0.0373 (3)	1.17050 (18)	0.0560 (7)
H8A	0.4573	0.0493	1.2309	0.067*
C9	0.3678 (4)	−0.0923 (3)	1.13745 (17)	0.0572 (7)
H9A	0.3983	−0.1654	1.1759	0.069*
C10	0.2876 (4)	−0.1141 (3)	1.04742 (16)	0.0492 (7)
H10A	0.2649	−0.2010	1.0250	0.059*
C11	0.2423 (3)	−0.0029 (2)	0.99178 (15)	0.0427 (6)
C12	0.2311 (5)	0.3684 (3)	0.9719 (2)	0.0769 (10)
H12A	0.1816	0.4126	0.9159	0.115*
H12B	0.3649	0.3933	0.9917	0.115*
H12C	0.1558	0.3951	1.0164	0.115*

	U11	U22	U33	U12	U13	U23
O	0.1073 (17)	0.0532 (12)	0.0506 (12)	0.0063 (10)	0.0123 (11)	0.0123 (9)
C1	0.0525 (15)	0.0477 (16)	0.0421 (14)	0.0037 (11)	0.0098 (11)	0.0010 (11)
N1	0.119 (2)	0.0507 (17)	0.0754 (19)	0.0038 (15)	0.0144 (16)	−0.0016 (14)
C2	0.0689 (18)	0.0507 (17)	0.0453 (15)	0.0021 (13)	0.0077 (12)	−0.0035 (13)
N2	0.116 (2)	0.089 (2)	0.0472 (15)	0.0060 (17)	0.0046 (14)	0.0044 (14)
C3	0.077 (2)	0.0517 (16)	0.0466 (17)	0.0008 (14)	0.0122 (14)	−0.0018 (13)
N3	0.0735 (15)	0.0372 (12)	0.0488 (13)	0.0004 (10)	0.0155 (11)	0.0023 (10)
C4	0.0474 (13)	0.0426 (14)	0.0429 (13)	0.0025 (10)	0.0112 (10)	0.0025 (11)
C5	0.0622 (16)	0.0464 (15)	0.0452 (15)	0.0013 (12)	0.0155 (12)	0.0052 (12)
C6	0.0472 (14)	0.0453 (15)	0.0451 (14)	0.0006 (11)	0.0135 (10)	0.0006 (11)
C7	0.0581 (16)	0.0550 (16)	0.0482 (15)	−0.0048 (12)	0.0118 (12)	−0.0078 (13)
C8	0.0581 (16)	0.0666 (19)	0.0415 (14)	0.0021 (13)	0.0042 (11)	−0.0007 (13)
C9	0.0619 (17)	0.0606 (18)	0.0477 (16)	0.0066 (13)	0.0060 (12)	0.0107 (13)
C10	0.0545 (15)	0.0454 (15)	0.0475 (14)	0.0045 (11)	0.0089 (11)	0.0044 (11)
C11	0.0436 (13)	0.0444 (14)	0.0408 (13)	0.0025 (10)	0.0095 (10)	0.0011 (11)
C12	0.122 (3)	0.0415 (17)	0.072 (2)	−0.0048 (16)	0.0294 (18)	−0.0016 (14)

O—C5	1.220 (3)	C6—C11	1.402 (3)
C1—C4	1.353 (4)	C7—C8	1.386 (4)
C1—C2	1.434 (4)	C7—H7A	0.9300
C1—C3	1.436 (4)	C8—C9	1.386 (4)
N1—C2	1.140 (4)	C8—H8A	0.9300
N2—C3	1.146 (3)	C9—C10	1.390 (4)
N3—C5	1.363 (3)	C9—H9A	0.9300
N3—C6	1.403 (3)	C10—C11	1.388 (3)
N3—C12	1.455 (4)	C10—H10A	0.9300
C4—C11	1.452 (3)	C12—H12A	0.9600
C4—C5	1.510 (4)	C12—H12B	0.9600
C6—C7	1.381 (3)	C12—H12C	0.9600
C4—C1—C2	121.6 (2)	C8—C7—H7A	121.3
C4—C1—C3	124.1 (2)	C9—C8—C7	121.8 (3)
C2—C1—C3	114.3 (2)	C9—C8—H8A	119.1
N1—C2—C1	178.9 (3)	C7—C8—H8A	119.1
N2—C3—C1	173.3 (3)	C8—C9—C10	120.7 (3)
C5—N3—C6	110.7 (2)	C8—C9—H9A	119.7
C5—N3—C12	124.2 (2)	C10—C9—H9A	119.7
C6—N3—C12	125.1 (2)	C11—C10—C9	118.4 (3)
C1—C4—C11	131.3 (2)	C11—C10—H10A	120.8
C1—C4—C5	122.5 (2)	C9—C10—H10A	120.8
C11—C4—C5	106.1 (2)	C10—C11—C6	120.0 (2)
O—C5—N3	126.8 (3)	C10—C11—C4	133.4 (2)
O—C5—C4	126.9 (2)	C6—C11—C4	106.7 (2)
N3—C5—C4	106.3 (2)	N3—C12—H12A	109.5
C7—C6—C11	121.9 (2)	N3—C12—H12B	109.5
C7—C6—N3	128.0 (2)	H12A—C12—H12B	109.5
C11—C6—N3	110.1 (2)	N3—C12—H12C	109.5
C6—C7—C8	117.3 (3)	H12A—C12—H12C	109.5
C6—C7—H7A	121.3	H12B—C12—H12C	109.5
C2—C1—C4—C11	0.1 (4)	C11—C6—C7—C8	−1.5 (4)
C3—C1—C4—C11	178.2 (2)	N3—C6—C7—C8	179.4 (2)
C2—C1—C4—C5	179.6 (2)	C6—C7—C8—C9	0.5 (4)
C3—C1—C4—C5	−2.3 (4)	C7—C8—C9—C10	0.4 (4)
C6—N3—C5—O	−178.5 (3)	C8—C9—C10—C11	−0.4 (4)
C12—N3—C5—O	0.5 (4)	C9—C10—C11—C6	−0.5 (4)
C6—N3—C5—C4	1.6 (3)	C9—C10—C11—C4	−179.6 (2)
C12—N3—C5—C4	−179.4 (2)	C7—C6—C11—C10	1.6 (4)
C1—C4—C5—O	−1.0 (4)	N3—C6—C11—C10	−179.3 (2)
C11—C4—C5—O	178.6 (2)	C7—C6—C11—C4	−179.1 (2)
C1—C4—C5—N3	178.9 (2)	N3—C6—C11—C4	0.0 (3)
C11—C4—C5—N3	−1.5 (3)	C1—C4—C11—C10	−0.4 (5)
C5—N3—C6—C7	178.0 (2)	C5—C4—C11—C10	−179.9 (3)
C12—N3—C6—C7	−0.9 (4)	C1—C4—C11—C6	−179.6 (2)
C5—N3—C6—C11	−1.1 (3)	C5—C4—C11—C6	0.9 (3)
C12—N3—C6—C11	179.9 (2)