2,2'-Dimeth-oxy-6,6'-dinitro-biphen-yl.

In the title compound, C(14)H(12)N(2)O(6), the half mol-ecule in the asymmetric unit of the cell is completed by a crystallographic twofold rotation axis, and the two benzene rings of the complete mol-ecule make a dihedral angle of 60.5 (3)°. Furthermore, inter-molecular weak C-H⋯O hydrogen bonds link adjacent mol-ecules, forming a two-dimensional sheet. These sheets are stablized by face-to-face weak π-π contacts [centroid-centroid distance = 3.682 (1) Å] between the nearly parallel [dihedral angle = 0.12 (7)°] benzene rings of the neighboring mol-ecules, resulting in a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Chen et al. (2001 ▶). For asymmetric synthesis using chiral ligands with C 2 symmetry, see: Jiang et al. (2001 ▶); García et al. (2002 ▶). For synthetic methods for chiral compounds, see: Brunel (2005 ▶); Kočovský et al. (2003 ▶). For related biphenyl structures, see: Fischer et al. (2007 ▶). For related structural data see: Yang et al. (2005 ▶).

Experimental

Crystal data

C14H12N2O6

M = 304.26

Monoclinic,

a = 18.236 (3) Å

b = 7.7826 (12) Å

c = 10.9079 (17) Å

β = 115.089 (2)°

V = 1402.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 294 K

0.30 × 0.18 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.979

5102 measured reflections

1298 independent reflections

1009 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.03

1298 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033790/si2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033790/si2193Isup2.hkl

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

C14H12N2O6	F(000) = 632
Mr = 304.26	Dx = 1.441 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1790 reflections
a = 18.236 (3) Å	θ = 2.5–25.7°
b = 7.7826 (12) Å	µ = 0.12 mm−1
c = 10.9079 (17) Å	T = 294 K
β = 115.089 (2)°	Block, yellow
V = 1402.0 (4) Å3	0.30 × 0.18 × 0.18 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1298 independent reflections
Radiation source: fine-focus sealed tube	1009 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.966, Tmax = 0.979	k = −9→9
5102 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.8036P] where P = (Fo2 + 2Fc2)/3
1298 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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
C1	0.49134 (9)	0.22562 (19)	0.67636 (14)	0.0387 (4)
C2	0.54245 (9)	0.2962 (2)	0.62577 (15)	0.0434 (4)
C3	0.52777 (12)	0.2896 (2)	0.49065 (17)	0.0546 (5)
H3	0.5639	0.3378	0.4607	0.066*
C4	0.45847 (12)	0.2102 (2)	0.40223 (17)	0.0588 (5)
H4	0.4471	0.2058	0.3107	0.071*
C5	0.40569 (11)	0.1370 (2)	0.44656 (16)	0.0540 (5)
H5	0.3589	0.0835	0.3852	0.065*
C6	0.42203 (9)	0.1426 (2)	0.58296 (15)	0.0444 (4)
C7	0.30000 (13)	−0.0071 (4)	0.5464 (2)	0.0944 (8)
H7A	0.2673	0.0767	0.4817	0.142*
H7B	0.2716	−0.0485	0.5971	0.142*
H7C	0.3110	−0.1012	0.4998	0.142*
N1	0.61559 (9)	0.3880 (2)	0.71661 (15)	0.0557 (4)
O1	0.37432 (7)	0.06986 (18)	0.63620 (11)	0.0594 (4)
O2	0.61327 (8)	0.47507 (17)	0.80791 (13)	0.0615 (4)
O3	0.67594 (9)	0.3739 (3)	0.69543 (17)	0.0967 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0399 (8)	0.0425 (8)	0.0345 (8)	0.0057 (6)	0.0166 (7)	0.0011 (6)
C2	0.0464 (9)	0.0454 (9)	0.0426 (8)	0.0044 (7)	0.0229 (7)	0.0023 (7)
C3	0.0722 (12)	0.0549 (10)	0.0508 (10)	0.0071 (9)	0.0399 (9)	0.0053 (8)
C4	0.0853 (14)	0.0566 (11)	0.0369 (8)	0.0117 (10)	0.0283 (10)	0.0036 (8)
C5	0.0610 (11)	0.0545 (10)	0.0372 (8)	0.0046 (9)	0.0119 (8)	−0.0031 (8)
C6	0.0452 (9)	0.0473 (9)	0.0388 (8)	0.0033 (7)	0.0159 (7)	0.0004 (7)
C7	0.0600 (13)	0.142 (2)	0.0750 (14)	−0.0445 (14)	0.0224 (12)	−0.0253 (15)
N1	0.0500 (8)	0.0679 (10)	0.0571 (9)	−0.0031 (7)	0.0302 (7)	0.0073 (8)
O1	0.0473 (7)	0.0794 (9)	0.0474 (7)	−0.0193 (6)	0.0162 (6)	−0.0058 (6)
O2	0.0612 (8)	0.0665 (8)	0.0570 (7)	−0.0133 (6)	0.0253 (6)	−0.0081 (7)
O3	0.0604 (9)	0.1503 (16)	0.0999 (12)	−0.0197 (10)	0.0538 (9)	−0.0120 (11)

C1—C2	1.383 (2)	C5—C6	1.389 (2)
C1—C6	1.400 (2)	C5—H5	0.9300
C1—C1i	1.500 (3)	C6—O1	1.3576 (19)
C2—C3	1.383 (2)	C7—O1	1.424 (2)
C2—N1	1.466 (2)	C7—H7A	0.9600
C3—C4	1.370 (3)	C7—H7B	0.9600
C3—H3	0.9300	C7—H7C	0.9600
C4—C5	1.371 (3)	N1—O2	1.2200 (18)
C4—H4	0.9300	N1—O3	1.2217 (18)
C2—C1—C6	116.51 (13)	C6—C5—H5	120.0
C2—C1—C1i	123.77 (15)	O1—C6—C5	124.06 (15)
C6—C1—C1i	119.63 (14)	O1—C6—C1	115.19 (13)
C1—C2—C3	123.51 (15)	C5—C6—C1	120.75 (15)
C1—C2—N1	119.86 (13)	O1—C7—H7A	109.5
C3—C2—N1	116.60 (14)	O1—C7—H7B	109.5
C4—C3—C2	118.11 (16)	H7A—C7—H7B	109.5
C4—C3—H3	120.9	O1—C7—H7C	109.5
C2—C3—H3	120.9	H7A—C7—H7C	109.5
C3—C4—C5	121.01 (15)	H7B—C7—H7C	109.5
C3—C4—H4	119.5	O2—N1—O3	123.39 (16)
C5—C4—H4	119.5	O2—N1—C2	119.06 (13)
C4—C5—C6	120.08 (17)	O3—N1—C2	117.55 (16)
C4—C5—H5	120.0	C6—O1—C7	118.46 (14)
C6—C1—C2—C3	0.7 (2)	C2—C1—C6—O1	178.01 (14)
C1i—C1—C2—C3	177.26 (13)	C1i—C1—C6—O1	1.26 (19)
C6—C1—C2—N1	178.92 (14)	C2—C1—C6—C5	−1.6 (2)
C1i—C1—C2—N1	−4.5 (2)	C1i—C1—C6—C5	−178.36 (13)
C1—C2—C3—C4	0.6 (3)	C1—C2—N1—O2	−36.5 (2)
N1—C2—C3—C4	−177.73 (16)	C3—C2—N1—O2	141.90 (16)
C2—C3—C4—C5	−0.9 (3)	C1—C2—N1—O3	144.16 (17)
C3—C4—C5—C6	0.0 (3)	C3—C2—N1—O3	−37.5 (2)
C4—C5—C6—O1	−178.25 (16)	C5—C6—O1—C7	−4.5 (3)
C4—C5—C6—C1	1.3 (3)	C1—C6—O1—C7	175.90 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O3ii	0.96	2.48	3.426 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O3i	0.96	2.48	3.426 (3)	169

Symmetry code: (i) .