2,6-Diphenyl­pyridine

In the title compound, C₁₇H₁₃N, the dihedral angles between the pyridine ring and the phenyl rings are 29.68 (18) and 26.58 (17)°. In the crystal structure, the mol­ecules are linked by a weak C—H...π inter­action, leading to [01] chains. There are no further significant inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.055
• wR factor = 0.163
• Data-to-parameter ratio = 9.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

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           27.50
           From the CIF: _reflns_number_total               1596
           Count of symmetry unique reflns         1598
           Completeness (_total/calc)             99.87%
           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
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The bonds and angles are in agreement with those found for related structures described by Crispini & Neve. (2002) and Silva et al.(1997). The angles between the mean planes of the pyridine rings and the phenyl rings are 29.68 (18)° (ring attached to C2), and 26.58 (17)° (ring attached to C6). The molecules are linked into chains along [011] by a weak C—H..π interaction (Fig. 2 and Table 1); C64—H64.·Cg1(-x + 1/2, y + 1/2, z - 1/2), where Cg1 is the centroid of the pyridine ring. There are no further intermolecular interactions.

Related literature

For related literature see: Crispini & Neve (2002); Silva et al.(1997). For a previous synthesis, see: Miyaura & Suzuki (1995).

S2. Experimental

The title compound was synthesized by adapting the procedure described by Miyaura & Suzuki (1995). A solution of 2,6-dibromopyridine (1.9 g), palladium(II) acetate (0.02 g) and phenylboronic acid (5.5 g) in N,N'-dimethylformamide was added to an aqueous solution of potassium carbonate (4.3 g). The mixture was refluxed for 5 h at 373 K. The cooled solution was extracted with 4 × 50 ml e thyl acetate/acetone (5:1 v/v) and the extract was filtered out. The solvent was evaporated under low pressure at 353 K. The resulting solid was recrystallized from ethanol to yield colourless blocks of (I). Found (%w) for C₁₇H₁₃N: C 88.97, H 5.32, N 5.71; calculated (%w): C 88.28, H 5.67, N 6.06. m.p. 351 K.

S3. Refinement

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. H atoms were treated as riding atoms with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: FLIPPER (Oszlányi & Süto, 2004, 2005; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick 1997) and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. A view of (I) with isplacement ellipsoids drawn at the 30% probability level (arbitrary spheres for the H atoms).
	Fig. 2. A stereoscopic view of symmetry related chains of molecules linked by the C—H..π interaction. H atoms not involved in the interaction are omitted for clarity.

2,6-Diphenylpyridine

Crystal data

C17H13N	Dx = 1.206 Mg m^−3
Mr = 231.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 1596 reflections
a = 16.1368 (16) Å	θ = 3.5–27.5°
b = 12.5371 (14) Å	µ = 0.07 mm^−1
c = 6.2969 (4) Å	T = 120 K
V = 1273.9 (2) Å^3	Block, colourless
Z = 4	0.70 × 0.32 × 0.14 mm
F(000) = 488

Data collection

Bruker–Nonius CCD diffractometer	1596 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1147 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.5°
π & ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −16→16
Tmin = 0.953, Tmax = 0.990	l = −8→8
29987 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0775P)^2 + 0.6523P] where P = (Fo^2 + 2Fc^2)/3
1596 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.25 e Å^−3

Special details

Experimental. The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.40272 (15)	0.4122 (2)	0.3621 (5)	0.0353 (6)
C2	0.4510 (2)	0.3407 (3)	0.4621 (6)	0.0356 (8)
C3	0.4702 (2)	0.3502 (3)	0.6756 (6)	0.0412 (8)
C4	0.4376 (2)	0.4338 (3)	0.7908 (7)	0.0443 (9)
C5	0.3893 (2)	0.5073 (3)	0.6890 (6)	0.0406 (8)
C6	0.37309 (19)	0.4956 (2)	0.4725 (6)	0.0345 (7)
C21	0.4814 (2)	0.2503 (3)	0.3325 (6)	0.0407 (8)
C22	0.5556 (2)	0.1994 (3)	0.3788 (8)	0.0503 (10)
C23	0.5826 (3)	0.1144 (3)	0.2567 (9)	0.0624 (13)
C24	0.5356 (3)	0.0782 (3)	0.0889 (9)	0.0635 (12)
C25	0.4618 (3)	0.1281 (3)	0.0410 (8)	0.0594 (12)
C26	0.4351 (3)	0.2137 (3)	0.1592 (6)	0.0468 (9)
C61	0.32310 (19)	0.5744 (3)	0.3538 (6)	0.0386 (8)
C62	0.3186 (2)	0.6797 (3)	0.4181 (7)	0.0512 (10)
C63	0.2743 (3)	0.7541 (3)	0.3035 (9)	0.0613 (12)
C64	0.2330 (2)	0.7237 (4)	0.1205 (9)	0.0629 (13)
C65	0.2361 (2)	0.6181 (3)	0.0548 (8)	0.0556 (11)
C66	0.2814 (2)	0.5446 (3)	0.1690 (6)	0.0434 (9)
H3	0.5055	0.2996	0.7421	0.049*
H4	0.4486	0.4402	0.9385	0.053*
H5	0.3668	0.5659	0.7652	0.049*
H22	0.5881	0.2231	0.4953	0.060*
H23	0.6338	0.0808	0.2888	0.075*
H24	0.5539	0.0192	0.0067	0.076*
H25	0.4292	0.1032	−0.0744	0.071*
H26	0.3846	0.2483	0.1229	0.056*
H62	0.3466	0.7013	0.5437	0.061*
H63	0.2721	0.8261	0.3500	0.074*
H64	0.2028	0.7748	0.0405	0.076*
H65	0.2069	0.5965	−0.0691	0.067*
H66	0.2842	0.4728	0.1214	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0342 (13)	0.0336 (14)	0.0381 (15)	−0.0040 (11)	0.0018 (14)	0.0020 (13)
C2	0.0335 (16)	0.0326 (16)	0.0408 (19)	−0.0040 (13)	0.0022 (15)	0.0032 (16)
C3	0.0344 (16)	0.049 (2)	0.041 (2)	−0.0077 (15)	−0.0038 (16)	0.0062 (18)
C4	0.0417 (18)	0.052 (2)	0.039 (2)	−0.0110 (16)	−0.0035 (17)	0.0011 (18)
C5	0.0391 (17)	0.0454 (19)	0.0371 (19)	−0.0072 (15)	0.0058 (16)	−0.0080 (17)
C6	0.0311 (15)	0.0338 (17)	0.0384 (19)	−0.0021 (13)	0.0009 (15)	−0.0015 (16)
C21	0.0453 (18)	0.0320 (15)	0.045 (2)	0.0002 (14)	0.0075 (18)	0.0058 (16)
C22	0.049 (2)	0.0365 (18)	0.066 (3)	0.0026 (15)	0.006 (2)	0.012 (2)
C23	0.063 (2)	0.039 (2)	0.085 (3)	0.0123 (18)	0.019 (3)	0.013 (2)
C24	0.090 (3)	0.0358 (18)	0.065 (3)	0.011 (2)	0.024 (3)	0.003 (2)
C25	0.088 (3)	0.0359 (19)	0.054 (3)	0.005 (2)	0.006 (3)	0.0004 (19)
C26	0.061 (2)	0.0344 (18)	0.045 (2)	0.0022 (16)	0.000 (2)	0.0007 (17)
C61	0.0307 (14)	0.0407 (17)	0.0444 (19)	0.0019 (13)	0.0034 (17)	−0.0021 (16)
C62	0.050 (2)	0.045 (2)	0.059 (3)	0.0085 (17)	0.0038 (19)	−0.005 (2)
C63	0.056 (2)	0.048 (2)	0.079 (4)	0.0154 (18)	0.011 (2)	0.000 (2)
C64	0.0384 (19)	0.068 (3)	0.083 (4)	0.0231 (19)	0.003 (2)	0.017 (3)
C65	0.0374 (19)	0.073 (3)	0.057 (3)	0.0057 (19)	−0.0049 (19)	0.005 (2)
C66	0.0331 (16)	0.0495 (19)	0.048 (2)	0.0032 (15)	0.0001 (18)	0.0013 (19)

Geometric parameters (Å, º)

N1—C6	1.344 (4)	C24—C25	1.378 (7)
N1—C2	1.344 (4)	C24—H24	0.95
C2—C3	1.385 (5)	C25—C26	1.376 (5)
C2—C21	1.481 (5)	C25—H25	0.95
C3—C4	1.378 (5)	C26—H26	0.95
C3—H3	0.95	C61—C62	1.383 (5)
C4—C5	1.368 (5)	C61—C66	1.395 (5)
C4—H4	0.95	C62—C63	1.379 (6)
C5—C6	1.395 (5)	C62—H62	0.95
C5—H5	0.95	C63—C64	1.384 (7)
C6—C61	1.478 (5)	C63—H63	0.95
C21—C22	1.387 (5)	C64—C65	1.388 (6)
C21—C26	1.400 (5)	C64—H64	0.95
C22—C23	1.384 (6)	C65—C66	1.380 (5)
C22—H22	0.95	C65—H65	0.95
C23—C24	1.378 (8)	C66—H66	0.95
C23—H23	0.95
C6—N1—C2	118.9 (3)	C25—C24—H24	120.2
N1—C2—C3	121.8 (3)	C23—C24—H24	120.2
N1—C2—C21	116.4 (3)	C26—C25—C24	120.5 (5)
C3—C2—C21	121.8 (3)	C26—C25—H25	119.8
C4—C3—C2	119.4 (4)	C24—C25—H25	119.8
C4—C3—H3	120.3	C25—C26—C21	120.6 (4)
C2—C3—H3	120.3	C25—C26—H26	119.7
C5—C4—C3	118.9 (4)	C21—C26—H26	119.7
C5—C4—H4	120.6	C62—C61—C66	118.3 (3)
C3—C4—H4	120.6	C62—C61—C6	121.2 (3)
C4—C5—C6	119.6 (3)	C66—C61—C6	120.4 (3)
C4—C5—H5	120.2	C63—C62—C61	121.3 (4)
C6—C5—H5	120.2	C63—C62—H62	119.3
N1—C6—C5	121.3 (3)	C61—C62—H62	119.3
N1—C6—C61	116.9 (3)	C62—C63—C64	119.9 (4)
C5—C6—C61	121.7 (3)	C62—C63—H63	120.0
C22—C21—C26	118.3 (4)	C64—C63—H63	120.0
C22—C21—C2	121.5 (4)	C63—C64—C65	119.6 (4)
C26—C21—C2	120.2 (3)	C63—C64—H64	120.2
C23—C22—C21	120.6 (4)	C65—C64—H64	120.2
C23—C22—H22	119.7	C66—C65—C64	120.0 (4)
C21—C22—H22	119.7	C66—C65—H65	120.0
C24—C23—C22	120.4 (4)	C64—C65—H65	120.0
C24—C23—H23	119.8	C65—C66—C61	120.8 (4)
C22—C23—H23	119.8	C65—C66—H66	119.6
C25—C24—C23	119.6 (4)	C61—C66—H66	119.6
C6—N1—C2—C3	0.7 (5)	C22—C23—C24—C25	0.9 (7)
C6—N1—C2—C21	179.7 (3)	C23—C24—C25—C26	0.1 (7)
N1—C2—C3—C4	1.4 (5)	C24—C25—C26—C21	−1.2 (6)
C21—C2—C3—C4	−177.5 (3)	C22—C21—C26—C25	1.3 (5)
C2—C3—C4—C5	−2.1 (5)	C2—C21—C26—C25	−178.4 (4)
C3—C4—C5—C6	0.8 (5)	N1—C6—C61—C62	−152.9 (3)
C2—N1—C6—C5	−2.1 (4)	C5—C6—C61—C62	26.8 (5)
C2—N1—C6—C61	177.6 (3)	N1—C6—C61—C66	25.0 (4)
C4—C5—C6—N1	1.4 (5)	C5—C6—C61—C66	−155.3 (3)
C4—C5—C6—C61	−178.3 (3)	C66—C61—C62—C63	−0.1 (6)
N1—C2—C21—C22	151.8 (3)	C6—C61—C62—C63	177.7 (4)
C3—C2—C21—C22	−29.2 (5)	C61—C62—C63—C64	0.2 (6)
N1—C2—C21—C26	−28.5 (5)	C62—C63—C64—C65	0.5 (6)
C3—C2—C21—C26	150.5 (3)	C63—C64—C65—C66	−1.3 (6)
C26—C21—C22—C23	−0.2 (5)	C64—C65—C66—C61	1.4 (6)
C2—C21—C22—C23	179.4 (4)	C62—C61—C66—C65	−0.7 (5)
C21—C22—C23—C24	−0.8 (6)	C6—C61—C66—C65	−178.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C64—H64···Cg1^i	0.95	2.74	3.534 (4)	142

Symmetry code: (i) −x+1/2, y+1/2, z−1/2.