2,5-Dimethyl-4'-nitro­biphen­yl

The title compound, C₁₄H₁₃NO₂, is a non-planar biphenyl derivative, in which the dihedral angle between the benzene rings is 62.65 (5) °.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.044
• wR factor = 0.123
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Bruker, 2004); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97; PLATON (Spek, 2003).

2,5-dimethyl-4'-nitrobiphenyl

Crystal data

C14H13NO2	F(000) = 480
Mr = 227.25	Dx = 1.311 Mg m^−3
Monoclinic, P21/c	Melting point: 371-372 K K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 6.7173 (1) Å	Cell parameters from 2901 reflections
b = 22.2902 (5) Å	θ = 0.9–68.3°
c = 7.8542 (2) Å	µ = 0.71 mm^−1
β = 101.711 (2)°	T = 173 K
V = 1151.53 (4) Å^3	Block, orange
Z = 4	0.40 × 0.35 × 0.20 mm

Data collection

Bruker Kappa APEX-II CCD diffractometer	1974 independent reflections
Radiation source: fine-focus sealed tube	1727 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 66.8°, θmin = 4.0°
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.764, Tmax = 0.871	k = −25→26
5271 measured reflections	l = −9→8

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)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0653P)^2 + 0.3546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
1974 reflections	Δρmax = 0.24 e Å^−3
157 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
O1	0.3356 (2)	0.57883 (6)	0.07224 (16)	0.0475 (4)
O2	0.28237 (18)	0.50827 (6)	−0.12031 (15)	0.0423 (4)
N1	0.28989 (19)	0.52715 (6)	0.02749 (17)	0.0350 (4)
C1	0.0864 (2)	0.36683 (7)	0.5346 (2)	0.0307 (4)
C2	−0.1115 (2)	0.34480 (7)	0.5261 (2)	0.0328 (4)
C3	−0.1435 (3)	0.30734 (7)	0.6590 (2)	0.0380 (4)
H3	−0.2769	0.2929	0.6572	0.046*
C4	0.0128 (3)	0.29020 (7)	0.7946 (2)	0.0386 (4)
H4	−0.0148	0.2641	0.8825	0.046*
C5	0.2090 (3)	0.31105 (7)	0.8025 (2)	0.0356 (4)
C6	0.2421 (2)	0.35017 (7)	0.6733 (2)	0.0331 (4)
H6	0.3745	0.3661	0.6794	0.040*
C7	0.1376 (2)	0.40818 (7)	0.4006 (2)	0.0298 (4)
C8	0.1171 (2)	0.39061 (7)	0.2275 (2)	0.0335 (4)
H8	0.0663	0.3517	0.1932	0.040*
C9	0.1696 (2)	0.42884 (7)	0.1048 (2)	0.0331 (4)
H9	0.1581	0.4164	−0.0125	0.040*
C10	0.2390 (2)	0.48541 (7)	0.1574 (2)	0.0300 (4)
C11	0.2617 (2)	0.50458 (7)	0.3270 (2)	0.0346 (4)
H11	0.3101	0.5438	0.3597	0.042*
C12	0.2124 (2)	0.46538 (7)	0.4486 (2)	0.0336 (4)
H12	0.2297	0.4776	0.5665	0.040*
C13	−0.2858 (2)	0.36077 (8)	0.3793 (2)	0.0414 (4)
H13A	−0.2830	0.3347	0.2794	0.062*
H13B	−0.2729	0.4027	0.3456	0.062*
H13C	−0.4148	0.3553	0.4174	0.062*
C14	0.3828 (3)	0.29178 (9)	0.9462 (2)	0.0470 (5)
H14A	0.3284	0.2731	1.0402	0.071*
H14B	0.4644	0.3269	0.9913	0.071*
H14C	0.4682	0.2628	0.9003	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0571 (8)	0.0405 (7)	0.0446 (8)	−0.0099 (6)	0.0096 (6)	0.0056 (6)
O2	0.0456 (7)	0.0533 (8)	0.0288 (7)	0.0033 (5)	0.0096 (5)	0.0038 (5)
N1	0.0305 (7)	0.0418 (8)	0.0322 (8)	0.0015 (6)	0.0053 (5)	0.0049 (6)
C1	0.0367 (8)	0.0279 (8)	0.0279 (8)	0.0012 (6)	0.0079 (6)	−0.0033 (6)
C2	0.0378 (8)	0.0289 (8)	0.0316 (9)	−0.0003 (6)	0.0071 (7)	−0.0045 (6)
C3	0.0413 (9)	0.0352 (9)	0.0389 (9)	−0.0070 (7)	0.0115 (7)	−0.0036 (7)
C4	0.0549 (10)	0.0300 (9)	0.0328 (9)	−0.0038 (7)	0.0133 (8)	0.0020 (7)
C5	0.0465 (10)	0.0296 (8)	0.0302 (8)	0.0027 (7)	0.0068 (7)	−0.0012 (7)
C6	0.0352 (8)	0.0325 (8)	0.0311 (9)	0.0009 (6)	0.0056 (7)	−0.0011 (6)
C7	0.0264 (7)	0.0334 (8)	0.0290 (8)	0.0032 (6)	0.0042 (6)	−0.0001 (6)
C8	0.0380 (9)	0.0306 (8)	0.0317 (9)	−0.0010 (7)	0.0066 (7)	−0.0028 (7)
C9	0.0358 (8)	0.0381 (9)	0.0255 (8)	0.0025 (7)	0.0061 (6)	−0.0028 (6)
C10	0.0274 (8)	0.0356 (9)	0.0273 (8)	0.0032 (6)	0.0061 (6)	0.0047 (6)
C11	0.0356 (9)	0.0331 (9)	0.0345 (9)	−0.0042 (7)	0.0059 (7)	−0.0032 (7)
C12	0.0370 (8)	0.0369 (9)	0.0261 (8)	−0.0020 (7)	0.0048 (6)	−0.0026 (6)
C13	0.0361 (9)	0.0455 (10)	0.0412 (10)	−0.0047 (7)	0.0044 (7)	−0.0004 (8)
C14	0.0542 (11)	0.0461 (11)	0.0381 (10)	0.0060 (8)	0.0030 (8)	0.0104 (8)

Geometric parameters (Å, º)

O1—N1	1.2252 (19)	C7—C8	1.394 (2)
O2—N1	1.2261 (17)	C8—C9	1.385 (2)
N1—C10	1.472 (2)	C8—H8	0.950
C1—C6	1.399 (2)	C9—C10	1.378 (2)
C1—C2	1.406 (2)	C9—H9	0.950
C1—C7	1.491 (2)	C10—C11	1.377 (2)
C2—C3	1.387 (2)	C11—C12	1.383 (2)
C2—C13	1.510 (2)	C11—H11	0.950
C3—C4	1.389 (2)	C12—H12	0.950
C3—H3	0.950	C13—H13A	0.980
C4—C5	1.387 (2)	C13—H13B	0.980
C4—H4	0.950	C13—H13C	0.980
C5—C6	1.389 (2)	C14—H14A	0.980
C5—C14	1.512 (2)	C14—H14B	0.980
C6—H6	0.950	C14—H14C	0.980
C7—C12	1.394 (2)
O1—N1—O2	123.64 (14)	C7—C8—H8	119.4
O1—N1—C10	118.38 (13)	C10—C9—C8	118.19 (14)
O2—N1—C10	117.97 (14)	C10—C9—H9	120.9
C6—C1—C2	119.62 (15)	C8—C9—H9	120.9
C6—C1—C7	118.09 (14)	C11—C10—C9	122.56 (15)
C2—C1—C7	122.29 (14)	C11—C10—N1	118.61 (14)
C3—C2—C1	117.64 (15)	C9—C10—N1	118.82 (14)
C3—C2—C13	120.16 (15)	C10—C11—C12	118.47 (15)
C1—C2—C13	122.19 (14)	C10—C11—H11	120.8
C2—C3—C4	122.31 (15)	C12—C11—H11	120.8
C2—C3—H3	118.8	C11—C12—C7	120.97 (15)
C4—C3—H3	118.8	C11—C12—H12	119.5
C5—C4—C3	120.36 (15)	C7—C12—H12	119.5
C5—C4—H4	119.8	C2—C13—H13A	109.5
C3—C4—H4	119.8	C2—C13—H13B	109.5
C4—C5—C6	117.99 (15)	H13A—C13—H13B	109.5
C4—C5—C14	121.38 (16)	C2—C13—H13C	109.5
C6—C5—C14	120.63 (16)	H13A—C13—H13C	109.5
C5—C6—C1	122.02 (15)	H13B—C13—H13C	109.5
C5—C6—H6	119.0	C5—C14—H14A	109.5
C1—C6—H6	119.0	C5—C14—H14B	109.5
C12—C7—C8	118.66 (14)	H14A—C14—H14B	109.5
C12—C7—C1	119.78 (14)	C5—C14—H14C	109.5
C8—C7—C1	121.55 (14)	H14A—C14—H14C	109.5
C9—C8—C7	121.13 (15)	H14B—C14—H14C	109.5
C9—C8—H8	119.4
C6—C1—C2—C3	0.5 (2)	C2—C1—C7—C8	−62.8 (2)
C7—C1—C2—C3	−178.98 (14)	C12—C7—C8—C9	0.0 (2)
C6—C1—C2—C13	−179.60 (15)	C1—C7—C8—C9	−178.48 (14)
C7—C1—C2—C13	0.9 (2)	C7—C8—C9—C10	−1.3 (2)
C1—C2—C3—C4	−1.7 (2)	C8—C9—C10—C11	1.4 (2)
C13—C2—C3—C4	178.42 (16)	C8—C9—C10—N1	−178.30 (13)
C2—C3—C4—C5	0.8 (3)	O1—N1—C10—C11	−5.5 (2)
C3—C4—C5—C6	1.3 (2)	O2—N1—C10—C11	175.11 (14)
C3—C4—C5—C14	−178.39 (16)	O1—N1—C10—C9	174.16 (14)
C4—C5—C6—C1	−2.5 (2)	O2—N1—C10—C9	−5.2 (2)
C14—C5—C6—C1	177.20 (15)	C9—C10—C11—C12	−0.1 (2)
C2—C1—C6—C5	1.6 (2)	N1—C10—C11—C12	179.55 (13)
C7—C1—C6—C5	−178.89 (14)	C10—C11—C12—C7	−1.2 (2)
C6—C1—C7—C12	−60.8 (2)	C8—C7—C12—C11	1.3 (2)
C2—C1—C7—C12	118.68 (17)	C1—C7—C12—C11	179.80 (14)
C6—C1—C7—C8	117.65 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O1^i	0.98	2.60	3.468 (2)	148
C12—H12···O2^ii	0.95	2.51	3.457 (2)	179

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1.