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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006156/qa0267sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006156/qa0267Isup2.hkl
Contains datablock I

CCDC reference: 146099

Computing details top

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) top
Crystal data top
C9H12N4Dx = 1.162 Mg m3
Mr = 176.23Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 474 reflections
a = 8.1341 (12) Åθ = 3.7–13.1°
b = 13.4171 (19) ŵ = 0.08 mm1
c = 9.2291 (14) ÅT = 293 K
V = 1007.2 (3) Å3Block, colourless
Z = 40.25 × 0.20 × 0.05 mm
F(000) = 376
Data collection top
Bruker Smart 1K CCD area-detector
diffractometer
2178 independent reflections
Radiation source: fine-focus sealed tube1691 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 27.1°, θmin = 2.7°
Absorption correction: multi-scan
(Blessing, 1995)
h = 710
Tmin = 0.981, Tmax = 0.996k = 1317
5674 measured reflectionsl = 1111
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)] = 0.033H-atom parameters constrained
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0426P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2178 reflectionsΔρmax = 0.10 e Å3
118 parametersΔρmin = 0.09 e Å3
1 restraintAbsolute structure: Flack (1983); 1005 Friedel
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (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
N10.22719 (12)0.96841 (7)0.23400 (13)0.0447 (3)
N20.3196 (2)0.75500 (12)0.0148 (2)0.1014 (6)
N30.0109 (2)1.27562 (12)0.0459 (2)0.0923 (5)
N40.68069 (17)0.96697 (11)0.2505 (2)0.0767 (4)
C10.09911 (15)0.89195 (9)0.2309 (2)0.0538 (3)
H1A0.03090.90140.14580.065*
H1B0.02970.89890.31580.065*
C20.17264 (19)0.78770 (10)0.2280 (2)0.0598 (4)
H2A0.25000.78060.30730.072*
H2B0.08600.73890.24130.072*
C30.2559 (2)0.76889 (11)0.0924 (2)0.0660 (5)
C40.18644 (17)1.05584 (10)0.14946 (17)0.0487 (3)
H4A0.16311.03480.05100.058*
H4B0.28241.09870.14590.058*
C50.03997 (17)1.11792 (10)0.20426 (17)0.0550 (4)
H5A0.05961.07820.19960.066*
H5B0.05821.13650.30460.066*
C60.0200 (2)1.20680 (12)0.1174 (2)0.0633 (4)
C70.28214 (15)0.98861 (11)0.38171 (17)0.0511 (4)
H7A0.29880.92570.43140.061*
H7B0.19611.02450.43250.061*
C80.43900 (17)1.04849 (11)0.38951 (17)0.0571 (4)
H8A0.41901.11430.34990.068*
H8B0.47021.05640.49030.068*
C90.57433 (19)1.00265 (12)0.31120 (18)0.0540 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0416 (5)0.0421 (6)0.0505 (7)0.0019 (4)0.0003 (6)0.0011 (6)
N20.1145 (15)0.0806 (11)0.1092 (15)0.0149 (10)0.0361 (12)0.0322 (10)
N30.1081 (13)0.0679 (9)0.1009 (13)0.0216 (9)0.0027 (10)0.0182 (10)
N40.0545 (8)0.0909 (10)0.0846 (11)0.0023 (8)0.0007 (8)0.0023 (9)
C10.0431 (7)0.0461 (7)0.0723 (10)0.0011 (6)0.0031 (8)0.0035 (8)
C20.0579 (8)0.0436 (7)0.0779 (11)0.0024 (6)0.0067 (9)0.0001 (8)
C30.0640 (9)0.0460 (8)0.0880 (14)0.0039 (7)0.0071 (10)0.0128 (8)
C40.0501 (8)0.0490 (7)0.0469 (7)0.0019 (6)0.0013 (6)0.0014 (6)
C50.0609 (8)0.0463 (7)0.0578 (10)0.0019 (6)0.0012 (7)0.0046 (7)
C60.0697 (10)0.0490 (9)0.0712 (11)0.0085 (8)0.0066 (9)0.0031 (9)
C70.0496 (8)0.0545 (8)0.0494 (8)0.0031 (6)0.0058 (7)0.0021 (7)
C80.0561 (9)0.0611 (9)0.0540 (9)0.0013 (7)0.0046 (8)0.0110 (7)
C90.0458 (8)0.0608 (9)0.0555 (9)0.0047 (7)0.0061 (7)0.0001 (7)
Geometric parameters (Å, º) top
N1—C41.4473 (18)C1—C21.5215 (19)
N1—C71.4600 (19)C2—C31.445 (3)
N1—C11.4624 (15)C4—C51.5391 (19)
N2—C31.133 (3)C5—C61.446 (2)
N3—C61.137 (2)C7—C81.509 (2)
N4—C91.136 (2)C8—C91.453 (2)
C4—N1—C7115.03 (11)N1—C4—C5116.02 (12)
C4—N1—C1113.25 (10)C6—C5—C4110.55 (13)
C7—N1—C1111.51 (12)N3—C6—C5176.85 (19)
N1—C1—C2111.41 (11)N1—C7—C8113.71 (11)
C3—C2—C1111.09 (14)C9—C8—C7113.03 (12)
N2—C3—C2179.0 (2)N4—C9—C8179.66 (19)
 

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