2,2'-Dimethoxy-biphen-yl.

The mol-ecule of the title compound, C(14)H(14)O(2), lies on a crystallographic twofold axis perpendicular to the central C-C bond; there is one half-mol-ecule in the asymmetric unit. The angle between the least-squares planes of the two aromatic rings is 66.94 (7)°. The meth-oxy group, with a twist angle of 10.69 (8)°, is slightly out of the plane of the benzene ring. In the crystal structure, C-H⋯π inter-actions are observed between adjacent mol-ecules along the c-axis direction.

Related literature

For related literature, see: Hargreaves et al. (1961 ▶); Yonezawa et al. (1993 ▶, 2000 ▶, 2003 ▶); Iyoda et al. (1990 ▶).

Experimental

Crystal data

C14H14O2

M = 214.25

Tetragonal,

a = 7.39307 (13) Å

c = 20.1623 (4) Å

V = 1102.02 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 193 K

0.40 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.813, T max = 0.934

20356 measured reflections

651 independent reflections

640 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.071

S = 1.14

651 reflections

75 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025178/fl2209sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025178/fl2209Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H14O2	Z = 4
Mr = 214.25	F000 = 456
Tetragonal, P41212	Dx = 1.291 Mg m−3
Hall symbol: P 4abw 2nw	Melting point = 427.0–427.5 K
a = 7.39307 (13) Å	Cu Kα radiation λ = 1.54187 Å
b = 7.39307 (13) Å	Cell parameters from 19640 reflections
c = 20.1623 (4) Å	θ = 4.4–68.2º
α = 90º	µ = 0.68 mm−1
β = 90º	T = 193 K
γ = 90º	Block, colorless
V = 1102.02 (4) Å3	0.40 × 0.20 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	651 independent reflections
Radiation source: rotating anode	640 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
Detector resolution: 10.00 pixels mm-1	θmax = 68.2º
T = 193 K	θmin = 6.4º
ω scans	h = −8→8
Absorption correction: numerical(NUMABS; Higashi, 1999)	k = −8→8
Tmin = 0.813, Tmax = 0.934	l = −24→24
20356 measured reflections

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.024	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.1367P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.071	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.15 e Å−3
651 reflections	Δρmin = −0.11 e Å−3
75 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0079 (11)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
O1	0.41372 (12)	0.38528 (13)	0.07663 (4)	0.0307 (3)
C1	0.64788 (17)	0.51523 (17)	0.01376 (5)	0.0237 (3)
C2	0.59201 (17)	0.38066 (18)	0.05852 (6)	0.0249 (3)
C3	0.71465 (19)	0.25505 (19)	0.08287 (6)	0.0297 (3)
H3	0.6753	0.1627	0.1123	0.036*
C4	0.89583 (18)	0.2648 (2)	0.06399 (7)	0.0332 (4)
H4	0.9793	0.1774	0.0800	0.040*
C5	0.95499 (19)	0.4005 (2)	0.02208 (6)	0.0338 (4)
H5	1.0792	0.4093	0.0105	0.041*
C6	0.83034 (18)	0.52435 (19)	−0.00291 (6)	0.0290 (3)
H6	0.8708	0.6171	−0.0320	0.035*
C7	0.3605 (2)	0.2711 (2)	0.13032 (7)	0.0364 (4)
H7A	0.2347	0.2969	0.1423	0.044*
H7B	0.4388	0.2939	0.1686	0.044*
H7C	0.3715	0.1442	0.1169	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0242 (5)	0.0351 (6)	0.0327 (5)	0.0000 (4)	0.0018 (4)	0.0101 (4)
C1	0.0259 (7)	0.0252 (7)	0.0201 (6)	−0.0028 (5)	−0.0028 (5)	−0.0028 (5)
C2	0.0244 (6)	0.0274 (7)	0.0229 (6)	−0.0016 (5)	−0.0030 (5)	−0.0025 (5)
C3	0.0327 (7)	0.0281 (7)	0.0282 (6)	−0.0012 (6)	−0.0051 (5)	0.0031 (6)
C4	0.0299 (7)	0.0359 (8)	0.0339 (7)	0.0067 (6)	−0.0073 (6)	−0.0019 (6)
C5	0.0238 (7)	0.0462 (9)	0.0313 (7)	0.0004 (6)	−0.0014 (5)	−0.0038 (6)
C6	0.0284 (7)	0.0350 (8)	0.0237 (6)	−0.0048 (6)	−0.0004 (6)	−0.0009 (6)
C7	0.0351 (8)	0.0410 (9)	0.0331 (6)	−0.0020 (6)	0.0055 (6)	0.0094 (6)

O1—C2	1.3682 (16)	C4—C5	1.383 (2)
O1—C7	1.4279 (16)	C4—H4	0.9500
C1—C6	1.3918 (18)	C5—C6	1.393 (2)
C1—C2	1.4053 (18)	C5—H5	0.9500
C1—C1i	1.494 (3)	C6—H6	0.9500
C2—C3	1.3876 (18)	C7—H7A	0.9800
C3—C4	1.3944 (19)	C7—H7B	0.9800
C3—H3	0.9500	C7—H7C	0.9800
C2—O1—C7	116.93 (11)	C4—C5—C6	119.25 (14)
C6—C1—C2	118.31 (12)	C4—C5—H5	120.4
C6—C1—C1i	120.99 (10)	C6—C5—H5	120.4
C2—C1—C1i	120.69 (10)	C1—C6—C5	121.46 (13)
O1—C2—C3	123.49 (12)	C1—C6—H6	119.3
O1—C2—C1	115.90 (11)	C5—C6—H6	119.3
C3—C2—C1	120.60 (12)	O1—C7—H7A	109.5
C2—C3—C4	119.78 (13)	O1—C7—H7B	109.5
C2—C3—H3	120.1	H7A—C7—H7B	109.5
C4—C3—H3	120.1	O1—C7—H7C	109.5
C5—C4—C3	120.53 (13)	H7A—C7—H7C	109.5
C5—C4—H4	119.7	H7B—C7—H7C	109.5
C3—C4—H4	119.7
C7—O1—C2—C3	9.30 (18)	C1—C2—C3—C4	1.5 (2)
C7—O1—C2—C1	−169.45 (11)	C2—C3—C4—C5	1.1 (2)
C6—C1—C2—O1	175.77 (11)	C3—C4—C5—C6	−2.1 (2)
C1i—C1—C2—O1	−2.66 (18)	C2—C1—C6—C5	2.0 (2)
C6—C1—C2—C3	−3.02 (18)	C1i—C1—C6—C5	−179.53 (12)
C1i—C1—C2—C3	178.54 (12)	C4—C5—C6—C1	0.5 (2)
O1—C2—C3—C4	−177.22 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ii	0.95	2.85	3.7266 (14)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1i	0.95	2.85	3.7266 (14)	154

Symmetry code: (i) . Cg1 is the centroid of atoms C1–C6.