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The title compound, C18H16N2, crystallizes with Z′ = {1 \over 4}. 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014353/bg2037sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014353/bg2037Isup2.hkl
Contains datablock I

CCDC reference: 646715

Key indicators

  • Single-crystal X-ray study
  • T = 174 K
  • Mean [sigma](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

Computing details top

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
C18H16N2F(000) = 1104
Mr = 260.33Dx = 1.223 Mg m3
Orthorhombic, FdddMo Kα radiation, λ = 0.71073 Å
Hall symbol: -F 2uv 2vwCell parameters from 3571 reflections
a = 7.4694 (19) Åθ = 3.0–27.5°
b = 16.812 (4) ŵ = 0.07 mm1
c = 22.514 (6) ÅT = 174 K
V = 2827.2 (12) Å3Prism, colourless
Z = 80.25 × 0.20 × 0.15 mm
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
820 independent reflections
Radiation source: fine-focus sealed tube731 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
[SADABS (Sheldrick, 2003; Blessing, 1995)]
h = 99
Tmin = 0.91, Tmax = 0.99k = 2121
7789 measured reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H 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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.22 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.37500.37500.21881 (7)0.0223 (4)
C20.30358 (16)0.30886 (7)0.24894 (5)0.0226 (3)
C30.30765 (16)0.30979 (7)0.31068 (5)0.0238 (3)
H30.258 (2)0.2640 (9)0.3321 (6)0.028 (4)*
C40.37500.37500.34197 (7)0.0220 (4)
C50.37500.37500.15477 (8)0.0258 (4)
C60.22408 (19)0.23974 (8)0.21552 (6)0.0277 (3)
H6D0.22660.25100.17280.042*0.170 (16)
H6E0.10000.23160.22830.042*0.170 (16)
H6F0.29390.19160.22370.042*0.170 (16)
H6A0.18700.19850.24370.042*0.830 (16)
H6B0.31370.21790.18820.042*0.830 (16)
H6C0.11980.25790.19290.042*0.830 (16)
N70.37500.37500.10388 (7)0.0355 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0233 (8)0.0227 (8)0.0208 (8)0.0027 (7)0.0000.000
C20.0219 (6)0.0218 (6)0.0240 (6)0.0023 (5)0.0003 (4)0.0009 (4)
C30.0258 (7)0.0216 (6)0.0240 (6)0.0002 (5)0.0011 (5)0.0020 (5)
C40.0228 (8)0.0225 (8)0.0208 (9)0.0016 (7)0.0000.000
C50.0307 (10)0.0214 (8)0.0252 (9)0.0016 (7)0.0000.000
C60.0317 (7)0.0260 (7)0.0255 (6)0.0031 (5)0.0008 (5)0.0036 (5)
N70.0505 (11)0.0305 (9)0.0254 (8)0.0036 (8)0.0000.000
Geometric parameters (Å, º) top
C1—C21.4075 (15)C5—N71.146 (2)
C1—C51.442 (2)C6—H6D0.9800
C2—C31.3905 (17)C6—H6E0.9800
C2—C61.5063 (17)C6—H6F0.9800
C3—C41.3968 (15)C6—H6A0.9800
C3—H30.982 (15)C6—H6B0.9800
C4—C4i1.487 (3)C6—H6C0.9800
C2—C1—C2ii122.38 (15)H6E—C6—H6F109.5
C2—C1—C5118.81 (8)C2—C6—H6A109.5
C3—C2—C1117.68 (12)H6D—C6—H6A141.1
C3—C2—C6121.11 (11)H6E—C6—H6A56.3
C1—C2—C6121.21 (11)H6F—C6—H6A56.3
C2—C3—C4121.39 (12)C2—C6—H6B109.5
C2—C3—H3118.3 (8)H6D—C6—H6B56.3
C4—C3—H3120.3 (8)H6E—C6—H6B141.1
C3ii—C4—C3119.44 (15)H6F—C6—H6B56.3
C3ii—C4—C4i120.28 (8)H6A—C6—H6B109.5
N7—C5—C1180.0C2—C6—H6C109.5
C2—C6—H6D109.5H6D—C6—H6C56.3
C2—C6—H6E109.5H6E—C6—H6C56.3
H6D—C6—H6E109.5H6F—C6—H6C141.1
C2—C6—H6F109.5H6A—C6—H6C109.5
H6D—C6—H6F109.5H6B—C6—H6C109.5
C2ii—C1—C2—C30.96 (8)C1—C2—C3—C41.96 (16)
C5—C1—C2—C3179.04 (8)C6—C2—C3—C4177.54 (10)
C2ii—C1—C2—C6178.54 (13)C2—C3—C4—C3ii1.02 (8)
C5—C1—C2—C61.46 (13)C2—C3—C4—C4i178.98 (8)
Symmetry codes: (i) x+3/4, y, z+3/4; (ii) x+3/4, y+3/4, z.
 

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