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Adipo­nitrile, C6H8N2, is a key inter­mediate in the synthesis of the polyamide Nylon 66 and is produced industrially on a large scale. We have determined the crystal and mol­ecular structure of adipo­nitrile by single-crystal X-ray analysis at 100 K, a suitable crystal (m.p. 275 K) having been grown from the melt at low temperature. The compound crystallizes in the monoclinic space group P21/c with Z = 2. In the crystal structure, the mol­ecule adopts an exact Ci-symmetric gaucheantigauche conformation of the C—C—C—C skeleton about an inversion centre. The mol­ecules are densely packed, with short intermolecular contacts between the α-H and nitrile N atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617014620/sk3672sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014620/sk3672Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2053229617014620/sk3672Isup3.mol
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617014620/sk3672sup4.pdf
Infrared spectrum of adiponitrile at room temperature.

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617014620/sk3672Isup5.cml
Supplementary material

CCDC reference: 1579139

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2014); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Hexane-1,6-dinitrile top
Crystal data top
C6H8N2Dx = 1.153 Mg m3
Mr = 108.14Melting point: 275 K
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 4.5031 (11) ÅCell parameters from 2360 reflections
b = 6.5860 (16) Åθ = 4.2–71.6°
c = 10.572 (3) ŵ = 0.57 mm1
β = 96.540 (6)°T = 100 K
V = 311.51 (13) Å3Cylinder, colourless
Z = 21.60 × 0.50 × 0.50 mm
F(000) = 116
Data collection top
Bruker X8 Proteum
diffractometer
604 independent reflections
Radiation source: rotating-anode X-ray tube593 reflections with I > 2σ(I)
Montel graded multilayer optics monochromatorRint = 0.042
Detector resolution: 66.67 pixels mm-1θmax = 72.0°, θmin = 7.9°
φ and ω scansh = 55
Absorption correction: gaussian
(SADABS; Bruker, 2012)
k = 78
Tmin = 0.597, Tmax = 0.783l = 1212
4525 measured reflections
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0706P)2 + 0.0851P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
604 reflectionsΔρmax = 0.19 e Å3
38 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL2017 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: dualExtinction coefficient: 0.20 (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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.1132 (3)0.62026 (19)0.19625 (11)0.0365 (5)
C10.2346 (3)0.6812 (2)0.28969 (12)0.0299 (5)
C20.3942 (3)0.7541 (2)0.40971 (12)0.0315 (5)
H2A0.2470750.8021550.4658120.038*
H2B0.5214090.8709680.3919410.038*
C30.5900 (3)0.5893 (2)0.47906 (11)0.0292 (5)
H3A0.7336030.5391560.4220130.035*
H3B0.7063370.6497910.5548870.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0440 (8)0.0359 (8)0.0285 (7)0.0028 (5)0.0002 (5)0.0020 (4)
C10.0328 (7)0.0290 (8)0.0280 (7)0.0017 (5)0.0043 (5)0.0044 (5)
C20.0373 (8)0.0297 (8)0.0270 (7)0.0027 (5)0.0014 (5)0.0002 (5)
C30.0282 (7)0.0336 (8)0.0253 (7)0.0041 (5)0.0004 (5)0.0010 (5)
Geometric parameters (Å, º) top
N1—C11.1458 (17)C2—H2B0.9900
C1—C21.4662 (18)C3—C3i1.523 (2)
C2—C31.5316 (18)C3—H3A0.9900
C2—H2A0.9900C3—H3B0.9900
N1—C1—C2178.49 (14)C3i—C3—C2112.98 (13)
C1—C2—C3112.39 (11)C3i—C3—H3A109.0
C1—C2—H2A109.1C2—C3—H3A109.0
C3—C2—H2A109.1C3i—C3—H3B109.0
C1—C2—H2B109.1C2—C3—H3B109.0
C3—C2—H2B109.1H3A—C3—H3B107.8
H2A—C2—H2B107.9
C1—C2—C3—C3i63.88 (17)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···N1ii0.992.633.5123 (18)149
C2—H2B···N1iii0.992.573.5436 (19)167
Symmetry codes: (ii) x, y+3/2, z+1/2; (iii) x+1, y+1/2, z+1/2.
 

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