4,4'-Dinon­yl-2,2'-bipyridine

The title compound, C₂₈H₄₄N₂, is one of the precursors of the amphiphilic heteroleptic ruthenium(II) sensitizer for DSC (dye-sensitized solar cells), and its molecule has a crystallographically imposed centre of symmetry. A segregated packing structure between the alk­yl chain layers and pyridine rings is observed.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.061
• wR factor = 0.154
• Data-to-parameter ratio = 21.5

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Computing details

Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

4,4'-Dinonyl-2,2'-bipyridine

Crystal data

C28H44N2	F(000) = 452
Mr = 408.65	Dx = 1.096 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2439 reflections
a = 5.5952 (5) Å	θ = 2.6–27.7°
b = 7.1862 (6) Å	µ = 0.06 mm^−1
c = 30.882 (3) Å	T = 173 K
β = 94.108 (2)°	Plate, colourless
V = 1238.52 (18) Å^3	0.45 × 0.42 × 0.11 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2949 independent reflections
Radiation source: fine-focus sealed tube	2465 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.366 pixels mm^-1	θmax = 28.0°, θmin = 2.6°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→7
Tmin = 0.962, Tmax = 0.993	l = −31→40
8628 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0658P)^2 + 0.4019P] where P = (Fo^2 + 2Fc^2)/3
2949 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.8339 (0.0058) x + 5.9598 (0.0055) y + 8.3872 (0.0172) z = 4.8263 (0.0071)

* -0.0627 (0.0011) C6 * -0.0149 (0.0012) C7 * 0.0381 (0.0014) C8 * 0.0223 (0.0013) C9 * 0.0517 (0.0014) C10 * 0.0090 (0.0013) C11 * 0.0430 (0.0014) C12 * -0.0558 (0.0013) C13 * -0.0307 (0.0012) C14

Rms deviation of fitted atoms = 0.0405

3.5000 (0.0026) x + 1.4339 (0.0046) y - 24.6170 (0.0111) z = 1.4149 (0.0040)

Angle to previous plane (with approximate e.s.d.) = 70.78 (0.06)

* -0.0024 (0.0010) N1 * 0.0069 (0.0010) C1 * -0.0049 (0.0010) C2 * -0.0013 (0.0010) C3 * 0.0056 (0.0011) C4 * -0.0039 (0.0011) C5 - 0.0123 (0.0023) C6 - 1.3296 (0.0026) C7

Rms deviation of fitted atoms = 0.0046

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.0963 (2)	0.9402 (2)	0.01068 (4)	0.0250 (3)
C2	0.2698 (2)	1.0152 (2)	0.04022 (4)	0.0261 (3)
H2	0.2653	1.1436	0.0475	0.031*
C3	0.4499 (2)	0.9014 (2)	0.05905 (4)	0.0270 (3)
C4	0.4448 (3)	0.7154 (2)	0.04722 (5)	0.0323 (4)
H4	0.5647	0.6324	0.0590	0.039*
C5	0.2636 (3)	0.6515 (2)	0.01811 (5)	0.0333 (4)
H5	0.2622	0.5232	0.0108	0.040*
C6	0.6418 (3)	0.9761 (2)	0.09116 (5)	0.0310 (4)
H6A	0.6348	1.1138	0.0908	0.037*
H6B	0.8004	0.9387	0.0818	0.037*
C7	0.6196 (2)	0.9084 (2)	0.13757 (4)	0.0277 (3)
H7A	0.4680	0.9554	0.1482	0.033*
H7B	0.6135	0.7707	0.1378	0.033*
C8	0.8295 (2)	0.9741 (2)	0.16805 (4)	0.0285 (3)
H8A	0.9806	0.9327	0.1562	0.034*
H8B	0.8303	1.1119	0.1684	0.034*
C9	0.8253 (3)	0.9042 (2)	0.21450 (5)	0.0283 (3)
H9A	0.6767	0.9479	0.2268	0.034*
H9B	0.8229	0.7664	0.2144	0.034*
C10	1.0408 (3)	0.9711 (2)	0.24323 (5)	0.0285 (3)
H10A	1.0408	1.1088	0.2435	0.034*
H10B	1.1887	0.9300	0.2303	0.034*
C11	1.0475 (3)	0.9014 (2)	0.28991 (5)	0.0284 (3)
H11A	0.9000	0.9424	0.3031	0.034*
H11B	1.0488	0.7637	0.2898	0.034*
C12	1.2649 (3)	0.9714 (2)	0.31775 (5)	0.0294 (3)
H12A	1.4117	0.9352	0.3038	0.035*
H12B	1.2595	1.1090	0.3187	0.035*
C13	1.2819 (3)	0.8977 (2)	0.36404 (5)	0.0308 (4)
H13A	1.2869	0.7600	0.3633	0.037*
H13B	1.1366	0.9351	0.3784	0.037*
C14	1.5027 (3)	0.9695 (3)	0.39065 (5)	0.0382 (4)
H14A	1.6469	0.9361	0.3762	0.057*
H14B	1.5102	0.9134	0.4196	0.057*
H14C	1.4930	1.1051	0.3932	0.057*
N1	0.0904 (2)	0.75979 (18)	−0.00028 (4)	0.0299 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0233 (7)	0.0328 (8)	0.0187 (6)	0.0016 (6)	0.0005 (5)	0.0010 (6)
C2	0.0267 (7)	0.0313 (7)	0.0203 (6)	0.0003 (6)	0.0003 (5)	−0.0008 (6)
C3	0.0234 (7)	0.0388 (8)	0.0184 (6)	−0.0009 (6)	−0.0008 (5)	0.0025 (6)
C4	0.0310 (8)	0.0383 (8)	0.0267 (7)	0.0074 (6)	−0.0041 (6)	0.0019 (6)
C5	0.0375 (8)	0.0307 (8)	0.0309 (8)	0.0048 (6)	−0.0048 (6)	−0.0030 (6)
C6	0.0255 (7)	0.0421 (9)	0.0244 (7)	−0.0040 (6)	−0.0043 (5)	0.0045 (6)
C7	0.0231 (7)	0.0365 (8)	0.0229 (7)	0.0003 (6)	−0.0017 (5)	0.0004 (6)
C8	0.0255 (7)	0.0352 (8)	0.0241 (7)	−0.0024 (6)	−0.0027 (5)	0.0006 (6)
C9	0.0262 (7)	0.0338 (8)	0.0243 (7)	−0.0017 (6)	−0.0024 (5)	0.0009 (6)
C10	0.0278 (7)	0.0336 (8)	0.0238 (7)	−0.0029 (6)	−0.0017 (5)	−0.0005 (6)
C11	0.0262 (7)	0.0335 (8)	0.0249 (7)	−0.0021 (6)	−0.0018 (5)	0.0010 (6)
C12	0.0274 (7)	0.0365 (8)	0.0239 (7)	−0.0037 (6)	−0.0017 (5)	0.0000 (6)
C13	0.0292 (7)	0.0388 (9)	0.0239 (7)	−0.0027 (6)	−0.0011 (5)	0.0019 (6)
C14	0.0350 (8)	0.0506 (10)	0.0276 (8)	−0.0050 (7)	−0.0071 (6)	0.0015 (7)
N1	0.0306 (7)	0.0332 (7)	0.0248 (6)	0.0028 (5)	−0.0045 (5)	−0.0032 (5)

Geometric parameters (Å, º)

C1—N1	1.340 (2)	C8—H8B	0.9900
C1—C2	1.3924 (19)	C9—C10	1.5230 (18)
C1—C1^i	1.494 (3)	C9—H9A	0.9900
C2—C3	1.392 (2)	C9—H9B	0.9900
C2—H2	0.9500	C10—C11	1.524 (2)
C3—C4	1.386 (2)	C10—H10A	0.9900
C3—C6	1.5073 (19)	C10—H10B	0.9900
C4—C5	1.384 (2)	C11—C12	1.5238 (19)
C4—H4	0.9500	C11—H11A	0.9900
C5—N1	1.3372 (19)	C11—H11B	0.9900
C5—H5	0.9500	C12—C13	1.521 (2)
C6—C7	1.527 (2)	C12—H12A	0.9900
C6—H6A	0.9900	C12—H12B	0.9900
C6—H6B	0.9900	C13—C14	1.524 (2)
C7—C8	1.5264 (18)	C13—H13A	0.9900
C7—H7A	0.9900	C13—H13B	0.9900
C7—H7B	0.9900	C14—H14A	0.9800
C8—C9	1.522 (2)	C14—H14B	0.9800
C8—H8A	0.9900	C14—H14C	0.9800
N1—C1—C2	122.93 (13)	C8—C9—H9A	109.1
N1—C1—C1^i	116.20 (15)	C10—C9—H9B	109.1
C2—C1—C1^i	120.88 (16)	C8—C9—H9B	109.1
C1—C2—C3	119.74 (14)	H9A—C9—H9B	107.9
C1—C2—H2	120.1	C9—C10—C11	114.34 (12)
C3—C2—H2	120.1	C9—C10—H10A	108.7
C4—C3—C2	117.13 (13)	C11—C10—H10A	108.7
C4—C3—C6	121.13 (13)	C9—C10—H10B	108.7
C2—C3—C6	121.73 (14)	C11—C10—H10B	108.7
C5—C4—C3	119.41 (14)	H10A—C10—H10B	107.6
C5—C4—H4	120.3	C12—C11—C10	112.94 (12)
C3—C4—H4	120.3	C12—C11—H11A	109.0
N1—C5—C4	123.91 (15)	C10—C11—H11A	109.0
N1—C5—H5	118.0	C12—C11—H11B	109.0
C4—C5—H5	118.0	C10—C11—H11B	109.0
C3—C6—C7	113.69 (12)	H11A—C11—H11B	107.8
C3—C6—H6A	108.8	C13—C12—C11	114.15 (12)
C7—C6—H6A	108.8	C13—C12—H12A	108.7
C3—C6—H6B	108.8	C11—C12—H12A	108.7
C7—C6—H6B	108.8	C13—C12—H12B	108.7
H6A—C6—H6B	107.7	C11—C12—H12B	108.7
C8—C7—C6	111.68 (12)	H12A—C12—H12B	107.6
C8—C7—H7A	109.3	C12—C13—C14	112.50 (13)
C6—C7—H7A	109.3	C12—C13—H13A	109.1
C8—C7—H7B	109.3	C14—C13—H13A	109.1
C6—C7—H7B	109.3	C12—C13—H13B	109.1
H7A—C7—H7B	107.9	C14—C13—H13B	109.1
C9—C8—C7	114.57 (12)	H13A—C13—H13B	107.8
C9—C8—H8A	108.6	C13—C14—H14A	109.5
C7—C8—H8A	108.6	C13—C14—H14B	109.5
C9—C8—H8B	108.6	H14A—C14—H14B	109.5
C7—C8—H8B	108.6	C13—C14—H14C	109.5
H8A—C8—H8B	107.6	H14A—C14—H14C	109.5
C10—C9—C8	112.32 (12)	H14B—C14—H14C	109.5
C10—C9—H9A	109.1	C5—N1—C1	116.86 (12)
N1—C1—C2—C3	1.2 (2)	C6—C7—C8—C9	−177.29 (13)
C1^i—C1—C2—C3	−178.79 (15)	C7—C8—C9—C10	178.98 (12)
C1—C2—C3—C4	−0.4 (2)	C8—C9—C10—C11	−178.82 (13)
C1—C2—C3—C6	179.94 (13)	C9—C10—C11—C12	−179.84 (12)
C2—C3—C4—C5	−0.6 (2)	C10—C11—C12—C13	−177.60 (13)
C6—C3—C4—C5	179.07 (14)	C11—C12—C13—C14	179.49 (13)
C3—C4—C5—N1	0.9 (2)	C4—C5—N1—C1	−0.1 (2)
C4—C3—C6—C7	−69.92 (19)	C2—C1—N1—C5	−1.0 (2)
C2—C3—C6—C7	109.72 (16)	C1^i—C1—N1—C5	179.06 (15)
C3—C6—C7—C8	175.11 (12)

Symmetry code: (i) −x, −y+2, −z.