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The title compound, C
18H
16N
2, crystallizes with
Z′ =
. The molecule exhibits 222 symmetry, with its centre at the intersection of three twofold axes, one of which traverses the molecule through the nitrile groups and the
ipso and
para ring atoms. The torsion angle between the rings is 50.3 (1)°. Adjacent molecules are involved in antiparallel CN
CN interactions and weak C—H
N hydrogen bonds.
Supporting information
CCDC reference: 646715
Key indicators
- Single-crystal X-ray study
- T = 174 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.113
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C5 ... 1.44 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); 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.
3,3',5,5'-Tetramethylbiphenyl-4,4'-dicarbonitrile
top
Crystal data top
C18H16N2 | F(000) = 1104 |
Mr = 260.33 | Dx = 1.223 Mg m−3 |
Orthorhombic, Fddd | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -F 2uv 2vw | Cell parameters from 3571 reflections |
a = 7.4694 (19) Å | θ = 3.0–27.5° |
b = 16.812 (4) Å | µ = 0.07 mm−1 |
c = 22.514 (6) Å | T = 174 K |
V = 2827.2 (12) Å3 | Prism, colourless |
Z = 8 | 0.25 × 0.20 × 0.15 mm |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 820 independent reflections |
Radiation source: fine-focus sealed tube | 731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan [SADABS (Sheldrick, 2003; Blessing, 1995)] | h = −9→9 |
Tmin = 0.91, Tmax = 0.99 | k = −21→21 |
7789 measured reflections | l = −28→28 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.05P)2 + 4.02P], where P = (Fo2 + 2Fc2)/3 |
820 reflections | (Δ/σ)max = 0.001 |
55 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.3750 | 0.3750 | 0.21881 (7) | 0.0223 (4) | |
C2 | 0.30358 (16) | 0.30886 (7) | 0.24894 (5) | 0.0226 (3) | |
C3 | 0.30765 (16) | 0.30979 (7) | 0.31068 (5) | 0.0238 (3) | |
H3 | 0.258 (2) | 0.2640 (9) | 0.3321 (6) | 0.028 (4)* | |
C4 | 0.3750 | 0.3750 | 0.34197 (7) | 0.0220 (4) | |
C5 | 0.3750 | 0.3750 | 0.15477 (8) | 0.0258 (4) | |
C6 | 0.22408 (19) | 0.23974 (8) | 0.21552 (6) | 0.0277 (3) | |
H6D | 0.2266 | 0.2510 | 0.1728 | 0.042* | 0.170 (16) |
H6E | 0.1000 | 0.2316 | 0.2283 | 0.042* | 0.170 (16) |
H6F | 0.2939 | 0.1916 | 0.2237 | 0.042* | 0.170 (16) |
H6A | 0.1870 | 0.1985 | 0.2437 | 0.042* | 0.830 (16) |
H6B | 0.3137 | 0.2179 | 0.1882 | 0.042* | 0.830 (16) |
H6C | 0.1198 | 0.2579 | 0.1929 | 0.042* | 0.830 (16) |
N7 | 0.3750 | 0.3750 | 0.10388 (7) | 0.0355 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0233 (8) | 0.0227 (8) | 0.0208 (8) | 0.0027 (7) | 0.000 | 0.000 |
C2 | 0.0219 (6) | 0.0218 (6) | 0.0240 (6) | 0.0023 (5) | −0.0003 (4) | −0.0009 (4) |
C3 | 0.0258 (7) | 0.0216 (6) | 0.0240 (6) | −0.0002 (5) | 0.0011 (5) | 0.0020 (5) |
C4 | 0.0228 (8) | 0.0225 (8) | 0.0208 (9) | 0.0016 (7) | 0.000 | 0.000 |
C5 | 0.0307 (10) | 0.0214 (8) | 0.0252 (9) | 0.0016 (7) | 0.000 | 0.000 |
C6 | 0.0317 (7) | 0.0260 (7) | 0.0255 (6) | −0.0031 (5) | −0.0008 (5) | −0.0036 (5) |
N7 | 0.0505 (11) | 0.0305 (9) | 0.0254 (8) | 0.0036 (8) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
C1—C2 | 1.4075 (15) | C5—N7 | 1.146 (2) |
C1—C5 | 1.442 (2) | C6—H6D | 0.9800 |
C2—C3 | 1.3905 (17) | C6—H6E | 0.9800 |
C2—C6 | 1.5063 (17) | C6—H6F | 0.9800 |
C3—C4 | 1.3968 (15) | C6—H6A | 0.9800 |
C3—H3 | 0.982 (15) | C6—H6B | 0.9800 |
C4—C4i | 1.487 (3) | C6—H6C | 0.9800 |
| | | |
C2—C1—C2ii | 122.38 (15) | H6E—C6—H6F | 109.5 |
C2—C1—C5 | 118.81 (8) | C2—C6—H6A | 109.5 |
C3—C2—C1 | 117.68 (12) | H6D—C6—H6A | 141.1 |
C3—C2—C6 | 121.11 (11) | H6E—C6—H6A | 56.3 |
C1—C2—C6 | 121.21 (11) | H6F—C6—H6A | 56.3 |
C2—C3—C4 | 121.39 (12) | C2—C6—H6B | 109.5 |
C2—C3—H3 | 118.3 (8) | H6D—C6—H6B | 56.3 |
C4—C3—H3 | 120.3 (8) | H6E—C6—H6B | 141.1 |
C3ii—C4—C3 | 119.44 (15) | H6F—C6—H6B | 56.3 |
C3ii—C4—C4i | 120.28 (8) | H6A—C6—H6B | 109.5 |
N7—C5—C1 | 180.0 | C2—C6—H6C | 109.5 |
C2—C6—H6D | 109.5 | H6D—C6—H6C | 56.3 |
C2—C6—H6E | 109.5 | H6E—C6—H6C | 56.3 |
H6D—C6—H6E | 109.5 | H6F—C6—H6C | 141.1 |
C2—C6—H6F | 109.5 | H6A—C6—H6C | 109.5 |
H6D—C6—H6F | 109.5 | H6B—C6—H6C | 109.5 |
| | | |
C2ii—C1—C2—C3 | −0.96 (8) | C1—C2—C3—C4 | 1.96 (16) |
C5—C1—C2—C3 | 179.04 (8) | C6—C2—C3—C4 | −177.54 (10) |
C2ii—C1—C2—C6 | 178.54 (13) | C2—C3—C4—C3ii | −1.02 (8) |
C5—C1—C2—C6 | −1.46 (13) | C2—C3—C4—C4i | 178.98 (8) |
Symmetry codes: (i) −x+3/4, y, −z+3/4; (ii) −x+3/4, −y+3/4, z. |
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