Tris(2-cyano­ethyl)­amine

In the title compound, N(CH₂CH₂CN)₃, (I), the three cyano­ethyl groups adopt a conformation with the CN groups oriented in the same direction, suggesting the compound may behave as a potential tripodal ligand.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C9H12N4	Dx = 1.162 Mg m^−3
Mr = 176.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 474 reflections
a = 8.1341 (12) Å	θ = 3.7–13.1°
b = 13.4171 (19) Å	µ = 0.08 mm^−1
c = 9.2291 (14) Å	T = 293 K
V = 1007.2 (3) Å^3	Block, colourless
Z = 4	0.25 × 0.20 × 0.05 mm
F(000) = 376

Data collection

Bruker Smart 1K CCD area-detector diffractometer	2178 independent reflections
Radiation source: fine-focus sealed tube	1691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.1°, θmin = 2.7°
Absorption correction: multi-scan (Blessing, 1995)	h = −7→10
Tmin = 0.981, Tmax = 0.996	k = −13→17
5674 measured reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0426P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2178 reflections	Δρmax = 0.10 e Å^−3
118 parameters	Δρmin = −0.09 e Å^−3
1 restraint	Absolute structure: Flack (1983); 1005 Friedel
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.22719 (12)	0.96841 (7)	0.23400 (13)	0.0447 (3)
N2	0.3196 (2)	0.75500 (12)	−0.0148 (2)	0.1014 (6)
N3	0.0109 (2)	1.27562 (12)	0.0459 (2)	0.0923 (5)
N4	0.68069 (17)	0.96697 (11)	0.2505 (2)	0.0767 (4)
C1	0.09911 (15)	0.89195 (9)	0.2309 (2)	0.0538 (3)
H1A	0.0309	0.9014	0.1458	0.065*
H1B	0.0297	0.8989	0.3158	0.065*
C2	0.17264 (19)	0.78770 (10)	0.2280 (2)	0.0598 (4)
H2A	0.2500	0.7806	0.3073	0.072*
H2B	0.0860	0.7389	0.2413	0.072*
C3	0.2559 (2)	0.76889 (11)	0.0924 (2)	0.0660 (5)
C4	0.18644 (17)	1.05584 (10)	0.14946 (17)	0.0487 (3)
H4A	0.1631	1.0348	0.0510	0.058*
H4B	0.2824	1.0987	0.1459	0.058*
C5	0.03997 (17)	1.11792 (10)	0.20426 (17)	0.0550 (4)
H5A	−0.0596	1.0782	0.1996	0.066*
H5B	0.0582	1.1365	0.3046	0.066*
C6	0.0200 (2)	1.20680 (12)	0.1174 (2)	0.0633 (4)
C7	0.28214 (15)	0.98861 (11)	0.38171 (17)	0.0511 (4)
H7A	0.2988	0.9257	0.4314	0.061*
H7B	0.1961	1.0245	0.4325	0.061*
C8	0.43900 (17)	1.04849 (11)	0.38951 (17)	0.0571 (4)
H8A	0.4190	1.1143	0.3499	0.068*
H8B	0.4702	1.0564	0.4903	0.068*
C9	0.57433 (19)	1.00265 (12)	0.31120 (18)	0.0540 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0416 (5)	0.0421 (6)	0.0505 (7)	−0.0019 (4)	0.0003 (6)	−0.0011 (6)
N2	0.1145 (15)	0.0806 (11)	0.1092 (15)	−0.0149 (10)	0.0361 (12)	−0.0322 (10)
N3	0.1081 (13)	0.0679 (9)	0.1009 (13)	0.0216 (9)	−0.0027 (10)	0.0182 (10)
N4	0.0545 (8)	0.0909 (10)	0.0846 (11)	0.0023 (8)	0.0007 (8)	−0.0023 (9)
C1	0.0431 (7)	0.0461 (7)	0.0723 (10)	−0.0011 (6)	0.0031 (8)	−0.0035 (8)
C2	0.0579 (8)	0.0436 (7)	0.0779 (11)	−0.0024 (6)	0.0067 (9)	−0.0001 (8)
C3	0.0640 (9)	0.0460 (8)	0.0880 (14)	−0.0039 (7)	0.0071 (10)	−0.0128 (8)
C4	0.0501 (8)	0.0490 (7)	0.0469 (7)	−0.0019 (6)	0.0013 (6)	0.0014 (6)
C5	0.0609 (8)	0.0463 (7)	0.0578 (10)	0.0019 (6)	0.0012 (7)	−0.0046 (7)
C6	0.0697 (10)	0.0490 (9)	0.0712 (11)	0.0085 (8)	−0.0066 (9)	−0.0031 (9)
C7	0.0496 (8)	0.0545 (8)	0.0494 (8)	0.0031 (6)	0.0058 (7)	0.0021 (7)
C8	0.0561 (9)	0.0611 (9)	0.0540 (9)	−0.0013 (7)	−0.0046 (8)	−0.0110 (7)
C9	0.0458 (8)	0.0608 (9)	0.0555 (9)	−0.0047 (7)	−0.0061 (7)	0.0001 (7)

Geometric parameters (Å, º)

N1—C4	1.4473 (18)	C1—C2	1.5215 (19)
N1—C7	1.4600 (19)	C2—C3	1.445 (3)
N1—C1	1.4624 (15)	C4—C5	1.5391 (19)
N2—C3	1.133 (3)	C5—C6	1.446 (2)
N3—C6	1.137 (2)	C7—C8	1.509 (2)
N4—C9	1.136 (2)	C8—C9	1.453 (2)
C4—N1—C7	115.03 (11)	N1—C4—C5	116.02 (12)
C4—N1—C1	113.25 (10)	C6—C5—C4	110.55 (13)
C7—N1—C1	111.51 (12)	N3—C6—C5	176.85 (19)
N1—C1—C2	111.41 (11)	N1—C7—C8	113.71 (11)
C3—C2—C1	111.09 (14)	C9—C8—C7	113.03 (12)
N2—C3—C2	179.0 (2)	N4—C9—C8	179.66 (19)