4,4′-Di­cyano­bi­phenyl

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—N...C—N interactions. In addition, there are a number of C—H...N interactions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.116
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C13      =       1.47 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C14      =       1.47 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.54
           From the CIF: _reflns_number_total               1249
           Count of symmetry unique reflns         1253
           Completeness (_total/calc)             99.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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

Crystal data

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) Å^3	0.30 × 0.10 × 0.05 mm
Z = 2

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 0.111P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)