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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.
Supporting information
CCDC reference: 189378
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.5 × 0.4 × 0.2 mm |
Z = 1 | |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.1488P)2 + 0.0774P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—O2i | 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) | O2i—O2—C2 | 114.5 (2) |
| | | |
O2—C2—C4—N1 | 171 (5) | C4—C2—O2—O2i | 4.7 (3) |
C3—C2—C4—N1 | 52 (5) | C3—C2—O2—O2i | 125.0 (3) |
C1—C2—C4—N1 | −71 (5) | C1—C2—O2—O2i | −116.2 (3) |
Symmetry code: (i) −x+1, −y+2, −z. |
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