2-[(1-Cyano-1-methyl­ethyl)­peroxy]-2-methyl­propane­nitrile

The title compound, C₈H₁₂N₂O₂, isolated from the reaction of cyclo­hexane­carbox­aldehyde, ethyl­amine, N-bromo­succin­imide and azobisisobutyro­nitrile, crystallizes in a centrosymmetric triclinic unit cell with one mol­ecule per unit cell. There is a centre of symmetry at the midpoint of the peroxide link. All bond lengths and angles are within expected ranges.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.230
• Data-to-parameter ratio = 16.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      1
                   O2  -C2  -C4  -N1    171.00  5.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      2
                   C3  -C2  -C4  -N1     52.00  5.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      3
                   C1  -C2  -C4  -N1    -71.00  5.00   1.555   1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

Computing details

Data collection: COLLECT; cell refinement: COLLECT (Nonius, 1998); data reduction: XCAD (McArdle, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

2-[(1-Cyano-1-methylethyl)peroxy]-2-methylpropanenitrile

Crystal data

C8H12N2O2	F(000) = 90
Mr = 168.2	Dx = 1.118 Mg m^−3
Triclinic, P1	Melting point = 339–341 K
a = 5.569 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 6.205 (3) Å	Cell parameters from 25 reflections
c = 7.875 (4) Å	θ = 9–15°
α = 77.94 (6)°	µ = 0.08 mm^−1
β = 79.17 (4)°	T = 295 K
γ = 71.29 (5)°	Rectangle, colorless
V = 249.9 (2) Å^3	0.5 × 0.4 × 0.2 mm
Z = 1

Data collection

Enraf-Nonius CAD-4 diffractometer	θmax = 25.0°, θmin = 2.7°
ω–2θ scans	h = −6→6
1088 measured reflections	k = −7→7
879 independent reflections	l = −1→9
723 reflections with I > 2σ(I)	3 standard reflections every 120 min
Rint = 0.023	intensity decay: 43%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.063	w = 1/[σ^2(Fo^2) + (0.1488P)^2 + 0.0774P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.230	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.27 e Å^−3
879 reflections	Δρmin = −0.38 e Å^−3
55 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5481 (5)	0.7857 (5)	0.3489 (4)	0.0575 (8)
H1A	0.6909	0.6552	0.3239	0.086*
H1B	0.4545	0.7472	0.4605	0.086*
H1C	0.609	0.9131	0.3517	0.086*
C2	0.3734 (4)	0.8522 (4)	0.2070 (3)	0.0430 (7)
C3	0.2791 (5)	0.6516 (5)	0.1962 (4)	0.0582 (8)
H3A	0.4229	0.521	0.1729	0.087*
H3B	0.1745	0.695	0.1035	0.087*
H3C	0.1803	0.6121	0.3052	0.087*
C4	0.1519 (5)	1.0539 (4)	0.2428 (3)	0.0548 (8)
N1	−0.0221 (5)	1.2005 (4)	0.2775 (4)	0.0852 (11)
O2	0.5333 (4)	0.9011 (3)	0.0369 (2)	0.0605 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0491 (15)	0.0646 (17)	0.0544 (15)	−0.0176 (12)	0.0047 (11)	−0.0087 (12)
C2	0.0371 (12)	0.0378 (12)	0.0458 (13)	−0.0092 (9)	0.0105 (9)	−0.0058 (9)
C3	0.0566 (15)	0.0540 (16)	0.0641 (16)	−0.0251 (13)	0.0079 (12)	−0.0101 (12)
C4	0.0490 (15)	0.0445 (14)	0.0571 (15)	−0.0117 (12)	0.0150 (11)	−0.0010 (11)
N1	0.0635 (16)	0.0554 (16)	0.099 (2)	0.0019 (13)	0.0363 (15)	−0.0042 (14)
O2	0.0544 (12)	0.0512 (11)	0.0637 (13)	−0.0133 (9)	0.0122 (9)	−0.0039 (8)

Geometric parameters (Å, º)

C1—C2	1.525 (4)	C2—C3	1.521 (3)
C1—H1A	0.96	C3—H3A	0.96
C1—H1B	0.96	C3—H3B	0.96
C1—H1C	0.96	C3—H3C	0.96
C2—C4	1.481 (3)	C4—N1	1.131 (3)
C2—O2	1.495 (3)	O2—O2^i	1.214 (4)
C2—C1—H1A	109.5	O2—C2—C1	106.59 (18)
C2—C1—H1B	109.5	C3—C2—C1	110.8 (2)
H1A—C1—H1B	109.5	C2—C3—H3A	109.5
C2—C1—H1C	109.5	C2—C3—H3B	109.5
H1A—C1—H1C	109.5	H3A—C3—H3B	109.5
H1B—C1—H1C	109.5	C2—C3—H3C	109.5
C4—C2—O2	112.11 (18)	H3A—C3—H3C	109.5
C4—C2—C3	109.6 (2)	H3B—C3—H3C	109.5
O2—C2—C3	107.34 (19)	N1—C4—C2	176.3 (2)
C4—C2—C1	110.4 (2)	O2^i—O2—C2	114.5 (2)
O2—C2—C4—N1	171 (5)	C4—C2—O2—O2^i	4.7 (3)
C3—C2—C4—N1	52 (5)	C3—C2—O2—O2^i	125.0 (3)
C1—C2—C4—N1	−71 (5)	C1—C2—O2—O2^i	−116.2 (3)

Symmetry code: (i) −x+1, −y+2, −z.