organic compounds
4,4′-Dicyanobiphenyl, C14H8N2, has a normal structure with a twist angle of 31.8 (2)°. The molecules stack with overlapping π systems and form chains held together by antiparallel C—NC—N interactions. In addition, there are a number of C—HN interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023274/om6185sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023274/om6185Isup2.hkl |
CCDC reference: 227034
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
4,4'-dicyanobiphenyl top
Crystal data top
C14H8N2 | F(000) = 212 |
Mr = 204.22 | Dx = 1.310 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2992 reflections |
a = 3.7798 (10) Å | θ = 2.5–27.3° |
b = 11.368 (4) Å | µ = 0.08 mm−1 |
c = 12.089 (4) Å | T = 173 K |
β = 94.54 (3)° | Needle, colorless |
V = 517.8 (3) Å3 | 0.30 × 0.10 × 0.05 mm |
Z = 2 |
Data collection top
Bruker SMART area-detector diffractometer | 1249 independent reflections |
Radiation source: fine-focus sealed tube | 1099 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002; Blessing, 1995) | h = −4→4 |
Tmin = 0.970, Tmax = 0.996 | k = −14→14 |
5937 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.044P)2 + 0.111P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max = 0.001 |
1249 reflections | Δρmax = 0.16 e Å−3 |
146 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: The absolute structure could not be determined. |
Primary atom site location: structure-invariant direct methods |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.6875 (10) | 0.1773 (3) | 0.8296 (3) | 0.0346 (9) | |
C2 | 0.7995 (11) | 0.2705 (4) | 0.8998 (3) | 0.0374 (9) | |
H2 | 0.9257 | 0.2552 | 0.9694 | 0.045* | |
C3 | 0.7248 (11) | 0.3849 (3) | 0.8671 (3) | 0.0350 (8) | |
H3 | 0.8001 | 0.4481 | 0.9147 | 0.042* | |
C4 | 0.5400 (10) | 0.4089 (3) | 0.7649 (3) | 0.0324 (8) | |
C5 | 0.4355 (10) | 0.3160 (3) | 0.6961 (3) | 0.0356 (9) | |
H5 | 0.3132 | 0.3316 | 0.6260 | 0.043* | |
C6 | 0.5058 (10) | 0.1998 (3) | 0.7276 (3) | 0.0359 (9) | |
H6 | 0.4302 | 0.1369 | 0.6798 | 0.043* | |
C7 | 0.4497 (9) | 0.5315 (3) | 0.7321 (3) | 0.0333 (9) | |
C8 | 0.3814 (10) | 0.6166 (3) | 0.8114 (3) | 0.0384 (9) | |
H8 | 0.4064 | 0.5966 | 0.8880 | 0.046* | |
C9 | 0.2783 (11) | 0.7292 (3) | 0.7801 (3) | 0.0400 (9) | |
H9 | 0.2305 | 0.7861 | 0.8346 | 0.048* | |
C10 | 0.2452 (10) | 0.7584 (3) | 0.6686 (3) | 0.0354 (8) | |
C11 | 0.3151 (11) | 0.6765 (4) | 0.5890 (3) | 0.0414 (9) | |
H11 | 0.2907 | 0.6971 | 0.5126 | 0.050* | |
C12 | 0.4210 (12) | 0.5644 (3) | 0.6210 (3) | 0.0375 (9) | |
H12 | 0.4750 | 0.5088 | 0.5661 | 0.045* | |
C13 | 0.7612 (11) | 0.0553 (4) | 0.8656 (3) | 0.0383 (9) | |
N13 | 0.8126 (11) | −0.0352 (4) | 0.8954 (3) | 0.0520 (10) | |
C14 | 0.1245 (11) | 0.8768 (4) | 0.6332 (3) | 0.0384 (9) | |
N14 | 0.0291 (11) | 0.9644 (4) | 0.6073 (3) | 0.0520 (9) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0327 (18) | 0.0335 (19) | 0.039 (2) | 0.0046 (17) | 0.0099 (16) | 0.0008 (17) |
C2 | 0.037 (2) | 0.044 (2) | 0.0313 (18) | 0.0046 (18) | 0.0036 (16) | 0.0022 (17) |
C3 | 0.037 (2) | 0.0309 (19) | 0.038 (2) | −0.0028 (17) | 0.0074 (17) | −0.0068 (15) |
C4 | 0.0306 (17) | 0.0318 (19) | 0.0354 (19) | −0.0005 (16) | 0.0060 (16) | −0.0058 (16) |
C5 | 0.035 (2) | 0.039 (2) | 0.0326 (19) | 0.0049 (18) | 0.0040 (16) | 0.0006 (16) |
C6 | 0.038 (2) | 0.034 (2) | 0.037 (2) | 0.0020 (16) | 0.0034 (17) | −0.0121 (15) |
C7 | 0.0258 (17) | 0.035 (2) | 0.040 (2) | −0.0010 (16) | 0.0054 (16) | 0.0016 (17) |
C8 | 0.043 (2) | 0.039 (2) | 0.0341 (19) | 0.0020 (19) | 0.0052 (16) | −0.0056 (17) |
C9 | 0.047 (2) | 0.0328 (19) | 0.040 (2) | 0.0017 (18) | 0.0067 (18) | −0.0022 (16) |
C10 | 0.0326 (18) | 0.033 (2) | 0.040 (2) | −0.0012 (16) | 0.0022 (16) | 0.0040 (16) |
C11 | 0.047 (2) | 0.041 (2) | 0.036 (2) | 0.002 (2) | 0.0032 (17) | 0.0063 (18) |
C12 | 0.043 (2) | 0.036 (2) | 0.0343 (18) | 0.0033 (17) | 0.0094 (18) | −0.0043 (16) |
C13 | 0.038 (2) | 0.049 (3) | 0.0279 (18) | 0.0044 (19) | 0.0020 (16) | −0.0032 (17) |
N13 | 0.060 (2) | 0.048 (2) | 0.047 (2) | 0.008 (2) | −0.0020 (19) | 0.0065 (19) |
C14 | 0.035 (2) | 0.036 (2) | 0.045 (2) | −0.0054 (17) | 0.0052 (17) | −0.0050 (19) |
N14 | 0.059 (2) | 0.049 (2) | 0.048 (2) | −0.003 (2) | 0.0006 (17) | 0.0044 (18) |
Geometric parameters (Å, º) top
C1—C6 | 1.387 (5) | C7—C8 | 1.401 (5) |
C1—C2 | 1.403 (5) | C8—C9 | 1.382 (5) |
C1—C13 | 1.473 (6) | C8—H8 | 0.9500 |
C2—C3 | 1.382 (6) | C9—C10 | 1.384 (5) |
C2—H2 | 0.9500 | C9—H9 | 0.9500 |
C3—C4 | 1.397 (5) | C10—C11 | 1.380 (6) |
C3—H3 | 0.9500 | C10—C14 | 1.474 (6) |
C4—C5 | 1.382 (5) | C11—C12 | 1.382 (6) |
C4—C7 | 1.482 (4) | C11—H11 | 0.9500 |
C5—C6 | 1.394 (6) | C12—H12 | 0.9500 |
C5—H5 | 0.9500 | C13—N13 | 1.102 (6) |
C6—H6 | 0.9500 | C14—N14 | 1.096 (6) |
C7—C12 | 1.390 (5) | ||
C6—C1—C2 | 120.2 (3) | C12—C7—C4 | 120.6 (3) |
C6—C1—C13 | 120.4 (3) | C8—C7—C4 | 121.2 (3) |
C2—C1—C13 | 119.4 (3) | C9—C8—C7 | 121.0 (4) |
C3—C2—C1 | 119.5 (3) | C9—C8—H8 | 119.5 |
C3—C2—H2 | 120.2 | C7—C8—H8 | 119.5 |
C1—C2—H2 | 120.2 | C8—C9—C10 | 119.4 (3) |
C2—C3—C4 | 120.9 (4) | C8—C9—H9 | 120.3 |
C2—C3—H3 | 119.6 | C10—C9—H9 | 120.3 |
C4—C3—H3 | 119.6 | C11—C10—C9 | 120.7 (3) |
C5—C4—C3 | 118.8 (3) | C11—C10—C14 | 119.1 (4) |
C5—C4—C7 | 120.6 (3) | C9—C10—C14 | 120.2 (3) |
C3—C4—C7 | 120.6 (3) | C10—C11—C12 | 119.6 (4) |
C4—C5—C6 | 121.4 (3) | C10—C11—H11 | 120.2 |
C4—C5—H5 | 119.3 | C12—C11—H11 | 120.2 |
C6—C5—H5 | 119.3 | C11—C12—C7 | 121.1 (4) |
C1—C6—C5 | 119.2 (3) | C11—C12—H12 | 119.4 |
C1—C6—H6 | 120.4 | C7—C12—H12 | 119.4 |
C5—C6—H6 | 120.4 | N13—C13—C1 | 178.0 (4) |
C12—C7—C8 | 118.2 (4) | N14—C14—C10 | 178.8 (5) |
Distances and angles (Å, °) in the C—H···N≡C contacts top
H | X | C—H | C—H···N | H···N | H..N≡C | C···N |
H3 | N13i | 0.95 | 151 | 2.63 | 115 | 3.366 (2) |
H6 | N14ii | 0.95 | 157 | 2.59 | 115 | 3.481 (6) |
H9 | N13iii | 0.95 | 148 | 2.71 | 135 | 3.550 (6) |
H12 | N14iiii | 0.95 | 119 | 2.77 | 125 | 3.325 (6) |
Symmetry codes: (i) 2-x, 1/2+y, 2-z; (ii) x, -1+y, z; (iii) -1+x, 1+y, z; (iiii) -x. -1/2+y, 1-z |