1,3-Dimethyl-1H-indole-2-carbonitrile.

The title compound, C(11)H(10)N(2), crystallizes with two mol-ecules in the asymmetric unit, both of which are essentially planar (r.m.s. deviations = 0.014 and 0.016 Å). In the crystal, aromatic π-π stacking inter-actions occur [shortest centroid-centroid separation = 3.5569 (11) Å].

Related literature

For the synthesis, see: Snyder & Eliel (1948 ▶).

Experimental

Crystal data

C11H10N2

M = 170.21

Monoclinic,

a = 8.8066 (18) Å

b = 15.359 (3) Å

c = 13.480 (3) Å

β = 95.67 (3)°

V = 1814.4 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.985, T max = 0.990

16175 measured reflections

4303 independent reflections

3462 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.03

4303 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024817/hb5013sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024817/hb5013Isup2.hkl

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

C11H10N2	F(000) = 720
Mr = 170.21	Dx = 1.246 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5208 reflections
a = 8.8066 (18) Å	θ = 2.0–27.9°
b = 15.359 (3) Å	µ = 0.08 mm−1
c = 13.480 (3) Å	T = 113 K
β = 95.67 (3)°	Block, colourless
V = 1814.4 (7) Å3	0.20 × 0.18 × 0.14 mm
Z = 8

Rigaku Saturn CCD area-detector diffractometer	4303 independent reflections
Radiation source: rotating anode	3462 reflections with I > 2σ(I)
confocla	Rint = 0.035
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.0°
ω and φ scans	h = −11→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −20→20
Tmin = 0.985, Tmax = 0.990	l = −17→17
16175 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0783P)2 + 0.2443P] where P = (Fo2 + 2Fc2)/3
4303 reflections	(Δ/σ)max = 0.003
238 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
N1	0.82816 (12)	0.53565 (7)	0.89373 (8)	0.0220 (2)
N2	0.54466 (13)	0.37505 (8)	0.91305 (9)	0.0323 (3)
N3	0.68373 (12)	0.02746 (7)	0.89897 (8)	0.0234 (3)
N4	0.88484 (17)	−0.16898 (9)	0.90325 (11)	0.0447 (4)
C1	0.94864 (16)	0.30650 (8)	0.85689 (11)	0.0294 (3)
H1A	1.0143	0.2841	0.9142	0.044*
H1B	0.9950	0.2936	0.7954	0.044*
H1C	0.8482	0.2786	0.8544	0.044*
C2	0.93090 (14)	0.40280 (8)	0.86704 (9)	0.0210 (3)
C3	1.04387 (14)	0.46744 (8)	0.85879 (9)	0.0201 (3)
C4	1.19845 (15)	0.46347 (8)	0.84089 (9)	0.0237 (3)
H4	1.2462	0.4092	0.8308	0.028*
C5	1.27868 (15)	0.54002 (9)	0.83840 (10)	0.0286 (3)
H5	1.3834	0.5382	0.8271	0.034*
C6	1.20941 (16)	0.62085 (9)	0.85218 (10)	0.0285 (3)
H6	1.2680	0.6725	0.8488	0.034*
C7	1.05797 (15)	0.62722 (8)	0.87060 (9)	0.0247 (3)
H7	1.0114	0.6820	0.8800	0.030*
C8	0.97653 (14)	0.54941 (8)	0.87480 (9)	0.0200 (3)
C9	0.80186 (14)	0.44673 (8)	0.88817 (9)	0.0211 (3)
C10	0.65833 (15)	0.40909 (8)	0.90293 (10)	0.0242 (3)
C11	0.71576 (15)	0.60235 (9)	0.91016 (10)	0.0278 (3)
H11A	0.7664	0.6514	0.9463	0.042*
H11B	0.6382	0.5779	0.9495	0.042*
H11C	0.6670	0.6226	0.8458	0.042*
C12	0.43756 (19)	−0.16808 (9)	0.85253 (11)	0.0339 (3)
H12A	0.4196	−0.1801	0.7825	0.051*
H12B	0.3426	−0.1699	0.8818	0.051*
H12C	0.5057	−0.2110	0.8837	0.051*
C13	0.50716 (16)	−0.07991 (8)	0.86744 (9)	0.0239 (3)
C14	0.43132 (15)	0.00185 (8)	0.86448 (9)	0.0223 (3)
C15	0.27685 (15)	0.02613 (9)	0.84775 (9)	0.0258 (3)
H15	0.1994	−0.0167	0.8352	0.031*
C16	0.24020 (16)	0.11338 (9)	0.85001 (10)	0.0280 (3)
H16	0.1363	0.1307	0.8392	0.034*
C17	0.35452 (16)	0.17728 (9)	0.86808 (10)	0.0277 (3)
H17	0.3258	0.2369	0.8689	0.033*
C18	0.50620 (16)	0.15567 (8)	0.88453 (10)	0.0244 (3)
H18	0.5827	0.1991	0.8961	0.029*
C19	0.54362 (14)	0.06698 (8)	0.88352 (9)	0.0205 (3)
C20	0.66012 (16)	−0.06165 (8)	0.88826 (9)	0.0241 (3)
C21	0.78416 (17)	−0.12122 (9)	0.89733 (11)	0.0306 (3)
C22	0.83057 (15)	0.07062 (9)	0.91704 (11)	0.0300 (3)
H22A	0.8496	0.1053	0.8585	0.045*
H22B	0.9112	0.0268	0.9295	0.045*
H22C	0.8301	0.1088	0.9753	0.045*

	U11	U22	U33	U12	U13	U23
N1	0.0207 (5)	0.0209 (5)	0.0245 (6)	0.0012 (4)	0.0027 (4)	−0.0009 (4)
N2	0.0231 (6)	0.0319 (6)	0.0425 (7)	−0.0034 (5)	0.0063 (5)	−0.0043 (5)
N3	0.0229 (6)	0.0213 (5)	0.0262 (6)	0.0001 (4)	0.0027 (4)	0.0008 (4)
N4	0.0502 (9)	0.0360 (7)	0.0480 (9)	0.0171 (7)	0.0053 (7)	0.0000 (6)
C1	0.0278 (7)	0.0219 (6)	0.0387 (8)	0.0004 (5)	0.0039 (6)	0.0009 (5)
C2	0.0196 (6)	0.0219 (6)	0.0211 (6)	−0.0003 (5)	0.0001 (5)	0.0009 (5)
C3	0.0202 (6)	0.0211 (6)	0.0189 (6)	−0.0001 (5)	0.0007 (5)	0.0012 (4)
C4	0.0210 (6)	0.0268 (6)	0.0232 (6)	0.0013 (5)	0.0023 (5)	0.0017 (5)
C5	0.0211 (6)	0.0385 (8)	0.0264 (7)	−0.0046 (6)	0.0028 (5)	0.0034 (6)
C6	0.0296 (7)	0.0278 (7)	0.0277 (7)	−0.0104 (6)	0.0010 (6)	0.0027 (5)
C7	0.0283 (7)	0.0212 (6)	0.0242 (7)	−0.0019 (5)	0.0008 (5)	−0.0004 (5)
C8	0.0202 (6)	0.0220 (6)	0.0174 (6)	0.0005 (5)	0.0001 (5)	0.0007 (4)
C9	0.0199 (6)	0.0222 (6)	0.0210 (6)	−0.0018 (5)	0.0011 (5)	0.0010 (5)
C10	0.0226 (6)	0.0245 (6)	0.0254 (7)	0.0011 (5)	0.0022 (5)	−0.0022 (5)
C11	0.0246 (7)	0.0275 (6)	0.0321 (7)	0.0058 (5)	0.0064 (6)	−0.0014 (5)
C12	0.0435 (9)	0.0250 (7)	0.0330 (8)	−0.0067 (6)	0.0024 (6)	−0.0010 (5)
C13	0.0305 (7)	0.0211 (6)	0.0201 (6)	−0.0028 (5)	0.0028 (5)	0.0001 (5)
C14	0.0252 (7)	0.0236 (6)	0.0182 (6)	−0.0034 (5)	0.0030 (5)	−0.0010 (5)
C15	0.0237 (7)	0.0317 (7)	0.0220 (7)	−0.0034 (6)	0.0015 (5)	−0.0013 (5)
C16	0.0234 (7)	0.0355 (7)	0.0248 (7)	0.0037 (6)	0.0013 (5)	0.0005 (5)
C17	0.0300 (7)	0.0254 (6)	0.0276 (7)	0.0055 (6)	0.0024 (6)	0.0018 (5)
C18	0.0266 (7)	0.0213 (6)	0.0252 (7)	−0.0016 (5)	0.0019 (5)	0.0010 (5)
C19	0.0204 (6)	0.0220 (6)	0.0192 (6)	−0.0001 (5)	0.0018 (5)	0.0009 (4)
C20	0.0296 (7)	0.0200 (6)	0.0231 (6)	0.0026 (5)	0.0045 (5)	0.0013 (5)
C21	0.0382 (8)	0.0249 (6)	0.0292 (7)	0.0052 (6)	0.0053 (6)	−0.0001 (5)
C22	0.0216 (7)	0.0292 (7)	0.0384 (8)	−0.0025 (6)	−0.0013 (6)	0.0030 (6)

N1—C8	1.3722 (16)	C9—C10	1.4217 (17)
N1—C9	1.3860 (16)	C11—H11A	0.9800
N1—C11	1.4566 (16)	C11—H11B	0.9800
N2—C10	1.1493 (17)	C11—H11C	0.9800
N3—C19	1.3724 (16)	C12—C13	1.4917 (18)
N3—C20	1.3897 (16)	C12—H12A	0.9600
N3—C22	1.4522 (17)	C12—H12B	0.9600
N4—C21	1.1474 (19)	C12—H12C	0.9600
C1—C2	1.4949 (17)	C13—C20	1.3774 (19)
C1—H1A	0.9800	C13—C14	1.4211 (18)
C1—H1B	0.9800	C14—C15	1.4071 (19)
C1—H1C	0.9800	C14—C19	1.4123 (18)
C2—C9	1.3754 (17)	C15—C16	1.3794 (19)
C2—C3	1.4177 (17)	C15—H15	0.9500
C3—C4	1.4072 (18)	C16—C17	1.410 (2)
C3—C8	1.4172 (17)	C16—H16	0.9500
C4—C5	1.3739 (19)	C17—C18	1.3730 (19)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.404 (2)	C18—C19	1.4019 (17)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.384 (2)	C20—C21	1.4209 (19)
C6—H6	0.9500	C22—H22A	0.9800
C7—C8	1.3978 (17)	C22—H22B	0.9800
C7—H7	0.9500	C22—H22C	0.9800
C8—N1—C9	107.39 (10)	N1—C11—H11C	109.5
C8—N1—C11	126.43 (11)	H11A—C11—H11C	109.5
C9—N1—C11	126.07 (11)	H11B—C11—H11C	109.5
C19—N3—C20	107.26 (11)	C13—C12—H12A	109.4
C19—N3—C22	126.58 (11)	C13—C12—H12B	109.5
C20—N3—C22	126.05 (11)	H12A—C12—H12B	109.5
C2—C1—H1A	109.5	C13—C12—H12C	109.5
C2—C1—H1B	109.5	H12A—C12—H12C	109.5
H1A—C1—H1B	109.5	H12B—C12—H12C	109.5
C2—C1—H1C	109.5	C20—C13—C14	105.86 (11)
H1A—C1—H1C	109.5	C20—C13—C12	126.36 (12)
H1B—C1—H1C	109.5	C14—C13—C12	127.78 (13)
C9—C2—C3	105.86 (11)	C15—C14—C19	119.34 (12)
C9—C2—C1	126.89 (12)	C15—C14—C13	133.08 (12)
C3—C2—C1	127.24 (11)	C19—C14—C13	107.58 (12)
C4—C3—C8	119.41 (11)	C16—C15—C14	118.59 (12)
C4—C3—C2	132.95 (11)	C16—C15—H15	120.7
C8—C3—C2	107.62 (11)	C14—C15—H15	120.7
C5—C4—C3	118.40 (12)	C15—C16—C17	121.03 (13)
C5—C4—H4	120.8	C15—C16—H16	119.5
C3—C4—H4	120.8	C17—C16—H16	119.5
C4—C5—C6	121.49 (13)	C18—C17—C16	121.76 (12)
C4—C5—H5	119.3	C18—C17—H17	119.1
C6—C5—H5	119.3	C16—C17—H17	119.1
C7—C6—C5	121.70 (12)	C17—C18—C19	117.34 (12)
C7—C6—H6	119.2	C17—C18—H18	121.3
C5—C6—H6	119.2	C19—C18—H18	121.3
C6—C7—C8	117.01 (12)	N3—C19—C18	129.57 (12)
C6—C7—H7	121.5	N3—C19—C14	108.50 (11)
C8—C7—H7	121.5	C18—C19—C14	121.94 (12)
N1—C8—C7	129.87 (11)	C13—C20—N3	110.79 (11)
N1—C8—C3	108.18 (10)	C13—C20—C21	127.91 (12)
C7—C8—C3	121.96 (12)	N3—C20—C21	121.29 (12)
C2—C9—N1	110.94 (11)	N4—C21—C20	178.97 (16)
C2—C9—C10	126.43 (12)	N3—C22—H22A	109.5
N1—C9—C10	122.63 (11)	N3—C22—H22B	109.5
N2—C10—C9	176.77 (14)	H22A—C22—H22B	109.5
N1—C11—H11A	109.5	N3—C22—H22C	109.5
N1—C11—H11B	109.5	H22A—C22—H22C	109.5
H11A—C11—H11B	109.5	H22B—C22—H22C	109.5
C9—C2—C3—C4	178.15 (14)	C20—C13—C14—C15	−179.38 (13)
C1—C2—C3—C4	−0.8 (2)	C12—C13—C14—C15	−0.1 (2)
C9—C2—C3—C8	−0.48 (14)	C20—C13—C14—C19	0.25 (14)
C1—C2—C3—C8	−179.42 (12)	C12—C13—C14—C19	179.58 (13)
C8—C3—C4—C5	−0.77 (19)	C19—C14—C15—C16	0.34 (18)
C2—C3—C4—C5	−179.27 (13)	C13—C14—C15—C16	179.94 (13)
C3—C4—C5—C6	−0.7 (2)	C14—C15—C16—C17	0.36 (19)
C4—C5—C6—C7	1.1 (2)	C15—C16—C17—C18	−0.3 (2)
C5—C6—C7—C8	−0.1 (2)	C16—C17—C18—C19	−0.5 (2)
C9—N1—C8—C7	179.28 (12)	C20—N3—C19—C18	−178.96 (13)
C11—N1—C8—C7	2.9 (2)	C22—N3—C19—C18	−2.4 (2)
C9—N1—C8—C3	−0.91 (14)	C20—N3—C19—C14	0.89 (14)
C11—N1—C8—C3	−177.24 (11)	C22—N3—C19—C14	177.41 (12)
C6—C7—C8—N1	178.39 (12)	C17—C18—C19—N3	−178.95 (12)
C6—C7—C8—C3	−1.40 (19)	C17—C18—C19—C14	1.23 (19)
C4—C3—C8—N1	−177.98 (11)	C15—C14—C19—N3	178.98 (11)
C2—C3—C8—N1	0.87 (14)	C13—C14—C19—N3	−0.71 (14)
C4—C3—C8—C7	1.85 (19)	C15—C14—C19—C18	−1.17 (19)
C2—C3—C8—C7	−179.30 (11)	C13—C14—C19—C18	179.14 (11)
C3—C2—C9—N1	−0.08 (14)	C14—C13—C20—N3	0.30 (14)
C1—C2—C9—N1	178.86 (12)	C12—C13—C20—N3	−179.04 (12)
C3—C2—C9—C10	179.90 (12)	C14—C13—C20—C21	−178.78 (13)
C1—C2—C9—C10	−1.2 (2)	C12—C13—C20—C21	1.9 (2)
C8—N1—C9—C2	0.62 (14)	C19—N3—C20—C13	−0.75 (14)
C11—N1—C9—C2	176.97 (12)	C22—N3—C20—C13	−177.29 (12)
C8—N1—C9—C10	−179.36 (11)	C19—N3—C20—C21	178.41 (12)
C11—N1—C9—C10	−3.01 (19)	C22—N3—C20—C21	1.86 (19)
C2—C9—C10—N2	−13 (3)	C13—C20—C21—N4	103 (10)
N1—C9—C10—N2	167 (3)	N3—C20—C21—N4	−76 (10)