Dimethyl 2,2'-di-nitro-biphenyl-4,4'-di-carboxyl-ate.

The title compound, C16H12N2O8, exhibits two near-planar aromatic ester groups with ar-yl-ester dihedral angles of 2.1 (2) and 4.2 (3)°. The dihedral angle between the aromatic rings is 58.0 (1)°. The two nitro groups are tilted slightly from the plane of the aromatic rings, making dihedral angles of 14.1 (1) and 8.2 (2)°. In the crystal, mol-ecules are connected by weak C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Ol’khovik et al. (2008 ▶). For the structure of 2,2′-di­nitro­biphenyl-4,4′-di­carb­oxy­lic acid, see: Wu et al. (2010 ▶). For metal-organic frameworks and coordination polymers featuring this linker, see: Qu (2007 ▶); Li, Zhou et al. (2011 ▶); Li, Li et al. (2011 ▶); Li, Zhang et al. (2011 ▶); Zhang, Ma et al. (2011 ▶); Zhang, Jing et al. (2011 ▶); Li, Yang et al. (2012 ▶); Zhang, Li et al. (2012 ▶).

Experimental

Crystal data

C16H12N2O8

M = 360.28

Triclinic,

a = 8.0520 (5) Å

b = 10.4193 (7) Å

c = 10.5310 (11) Å

α = 108.423 (4)°

β = 95.142 (4)°

γ = 111.617 (3)°

V = 757.71 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 90 K

0.28 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.981

9906 measured reflections

2787 independent reflections

2297 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.02

2787 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814003067/ff2126sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003067/ff2126Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003067/ff2126Isup3.cml

CCDC reference: 986204

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H12N2O8	Z = 2
Mr = 360.28	F(000) = 372
Triclinic, P1	Dx = 1.579 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0520 (5) Å	Cell parameters from 5153 reflections
b = 10.4193 (7) Å	θ = 2.8–25.4°
c = 10.5310 (11) Å	µ = 0.13 mm−1
α = 108.423 (4)°	T = 90 K
β = 95.142 (4)°	BLOCK, yellow
γ = 111.617 (3)°	0.28 × 0.20 × 0.15 mm
V = 757.71 (11) Å3

Bruker APEXII CCD diffractometer	2787 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.965, Tmax = 0.981	k = −12→12
9906 measured reflections	l = −12→12

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.234P] where P = (Fo2 + 2Fc2)/3
2787 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 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 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	0.28379 (14)	−0.04398 (11)	0.86338 (10)	0.0223 (3)
O2	0.02811 (15)	−0.01405 (13)	0.81152 (11)	0.0283 (3)
O3	0.80395 (15)	0.15657 (14)	0.70622 (13)	0.0350 (3)
O4	0.80373 (15)	0.23016 (13)	0.53753 (11)	0.0283 (3)
O5	0.72326 (16)	0.49239 (12)	0.69694 (11)	0.0327 (3)
O6	0.93059 (15)	0.61445 (13)	0.61157 (11)	0.0323 (3)
O7	0.80462 (15)	0.55730 (12)	0.14341 (11)	0.0292 (3)
O8	0.56913 (17)	0.35679 (13)	−0.01199 (11)	0.0355 (3)
N1	0.72907 (16)	0.18850 (13)	0.62186 (13)	0.0196 (3)
N2	0.78359 (17)	0.51402 (14)	0.59936 (12)	0.0206 (3)
C1	0.1936 (2)	−0.12748 (18)	0.94307 (16)	0.0253 (4)
H1A	0.2829	−0.1467	0.9949	0.038*
H1B	0.0943	−0.2224	0.8810	0.038*
H1C	0.1427	−0.0698	1.0072	0.038*
C2	0.1814 (2)	0.00368 (16)	0.79992 (15)	0.0199 (3)
C3	0.2780 (2)	0.07985 (15)	0.71294 (14)	0.0181 (3)
C4	0.4574 (2)	0.10299 (15)	0.70668 (14)	0.0182 (3)
H4A	0.5234	0.0717	0.7606	0.022*
C5	0.53980 (19)	0.17125 (15)	0.62247 (15)	0.0179 (3)
C6	0.4489 (2)	0.21904 (15)	0.53960 (15)	0.0181 (3)
C7	0.2683 (2)	0.19281 (16)	0.54750 (15)	0.0199 (3)
H7A	0.2004	0.2214	0.4919	0.024*
C8	0.1845 (2)	0.12668 (16)	0.63336 (15)	0.0201 (3)
H8A	0.0622	0.1132	0.6379	0.024*
C9	0.5175 (2)	0.28358 (16)	0.43647 (15)	0.0186 (3)
C10	0.6699 (2)	0.41620 (16)	0.45972 (15)	0.0187 (3)
C11	0.7209 (2)	0.46404 (16)	0.35496 (15)	0.0196 (3)
H11A	0.8284	0.5524	0.3740	0.024*
C12	0.6138 (2)	0.38191 (16)	0.22211 (15)	0.0208 (3)
C13	0.4585 (2)	0.25263 (17)	0.19660 (16)	0.0232 (3)
H13A	0.3833	0.1967	0.1060	0.028*
C14	0.4123 (2)	0.20443 (16)	0.30184 (15)	0.0217 (3)
H14A	0.3060	0.1149	0.2819	0.026*
C15	0.6575 (2)	0.42811 (17)	0.10439 (16)	0.0239 (4)
C16	0.8490 (3)	0.6119 (2)	0.03466 (17)	0.0354 (4)
H16A	0.9564	0.7083	0.0729	0.053*
H16B	0.7443	0.6240	−0.0062	0.053*
H16C	0.8765	0.5404	−0.0362	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0235 (6)	0.0248 (6)	0.0241 (6)	0.0100 (5)	0.0094 (4)	0.0154 (5)
O2	0.0227 (6)	0.0362 (7)	0.0344 (7)	0.0134 (5)	0.0140 (5)	0.0205 (5)
O3	0.0253 (6)	0.0526 (8)	0.0442 (7)	0.0200 (6)	0.0117 (5)	0.0348 (6)
O4	0.0251 (6)	0.0383 (7)	0.0328 (6)	0.0153 (5)	0.0158 (5)	0.0230 (6)
O5	0.0419 (7)	0.0275 (6)	0.0197 (6)	0.0035 (5)	0.0098 (5)	0.0099 (5)
O6	0.0255 (6)	0.0306 (6)	0.0274 (6)	−0.0018 (5)	0.0033 (5)	0.0109 (5)
O7	0.0336 (7)	0.0274 (6)	0.0213 (6)	0.0032 (5)	0.0068 (5)	0.0140 (5)
O8	0.0512 (8)	0.0268 (6)	0.0189 (6)	0.0071 (6)	0.0035 (5)	0.0088 (5)
N1	0.0185 (7)	0.0177 (6)	0.0228 (7)	0.0066 (5)	0.0056 (5)	0.0087 (5)
N2	0.0227 (7)	0.0186 (6)	0.0208 (7)	0.0072 (6)	0.0059 (5)	0.0095 (5)
C1	0.0312 (9)	0.0242 (8)	0.0245 (8)	0.0097 (7)	0.0113 (7)	0.0149 (7)
C2	0.0200 (8)	0.0174 (7)	0.0190 (8)	0.0060 (6)	0.0042 (6)	0.0050 (6)
C3	0.0196 (8)	0.0153 (7)	0.0173 (7)	0.0064 (6)	0.0051 (6)	0.0042 (6)
C4	0.0207 (8)	0.0158 (7)	0.0170 (7)	0.0074 (6)	0.0029 (6)	0.0057 (6)
C5	0.0168 (7)	0.0160 (7)	0.0194 (7)	0.0065 (6)	0.0050 (6)	0.0049 (6)
C6	0.0213 (8)	0.0130 (7)	0.0173 (7)	0.0054 (6)	0.0044 (6)	0.0045 (6)
C7	0.0195 (8)	0.0194 (8)	0.0228 (8)	0.0094 (6)	0.0041 (6)	0.0090 (6)
C8	0.0184 (8)	0.0191 (8)	0.0223 (8)	0.0080 (6)	0.0066 (6)	0.0065 (6)
C9	0.0198 (8)	0.0174 (7)	0.0223 (8)	0.0106 (6)	0.0069 (6)	0.0083 (6)
C10	0.0200 (8)	0.0180 (7)	0.0183 (8)	0.0086 (6)	0.0042 (6)	0.0062 (6)
C11	0.0210 (8)	0.0160 (7)	0.0233 (8)	0.0078 (6)	0.0069 (6)	0.0087 (6)
C12	0.0263 (8)	0.0187 (8)	0.0203 (8)	0.0113 (7)	0.0069 (6)	0.0083 (6)
C13	0.0272 (8)	0.0191 (8)	0.0203 (8)	0.0074 (7)	0.0021 (6)	0.0073 (6)
C14	0.0218 (8)	0.0173 (7)	0.0248 (8)	0.0068 (6)	0.0040 (6)	0.0087 (6)
C15	0.0309 (9)	0.0197 (8)	0.0223 (9)	0.0111 (7)	0.0069 (7)	0.0089 (7)
C16	0.0409 (10)	0.0378 (10)	0.0272 (9)	0.0071 (8)	0.0099 (8)	0.0225 (8)

O1—C2	1.3363 (18)	C5—C6	1.405 (2)
O1—C1	1.4469 (17)	C6—C7	1.393 (2)
O2—C2	1.2024 (18)	C6—C9	1.494 (2)
O3—N1	1.2256 (16)	C7—C8	1.381 (2)
O4—N1	1.2188 (16)	C7—H7A	0.9500
O5—N2	1.2239 (16)	C8—H8A	0.9500
O6—N2	1.2197 (16)	C9—C14	1.392 (2)
O7—C15	1.3315 (19)	C9—C10	1.399 (2)
O7—C16	1.4486 (18)	C10—C11	1.383 (2)
O8—C15	1.1995 (19)	C11—C12	1.384 (2)
N1—C5	1.4682 (18)	C11—H11A	0.9500
N2—C10	1.4708 (19)	C12—C13	1.385 (2)
C1—H1A	0.9800	C12—C15	1.491 (2)
C1—H1B	0.9800	C13—C14	1.381 (2)
C1—H1C	0.9800	C13—H13A	0.9500
C2—C3	1.485 (2)	C14—H14A	0.9500
C3—C8	1.387 (2)	C16—H16A	0.9800
C3—C4	1.385 (2)	C16—H16B	0.9800
C4—C5	1.374 (2)	C16—H16C	0.9800
C4—H4A	0.9500
C2—O1—C1	115.18 (11)	C6—C7—H7A	118.9
C15—O7—C16	115.00 (12)	C3—C8—C7	120.31 (14)
O4—N1—O3	122.78 (12)	C3—C8—H8A	119.8
O4—N1—C5	119.80 (12)	C7—C8—H8A	119.8
O3—N1—C5	117.40 (12)	C14—C9—C10	116.34 (13)
O6—N2—O5	123.65 (13)	C14—C9—C6	115.67 (13)
O6—N2—C10	118.19 (12)	C10—C9—C6	127.94 (13)
O5—N2—C10	118.13 (12)	C11—C10—C9	122.64 (13)
O1—C1—H1A	109.5	C11—C10—N2	116.29 (13)
O1—C1—H1B	109.5	C9—C10—N2	121.07 (13)
H1A—C1—H1B	109.5	C12—C11—C10	119.37 (14)
O1—C1—H1C	109.5	C12—C11—H11A	120.3
H1A—C1—H1C	109.5	C10—C11—H11A	120.3
H1B—C1—H1C	109.5	C11—C12—C13	119.30 (14)
O2—C2—O1	123.67 (14)	C11—C12—C15	122.49 (14)
O2—C2—C3	124.01 (14)	C13—C12—C15	118.20 (14)
O1—C2—C3	112.32 (12)	C14—C13—C12	120.55 (14)
C8—C3—C4	118.93 (13)	C14—C13—H13A	119.7
C8—C3—C2	118.95 (13)	C12—C13—H13A	119.7
C4—C3—C2	122.11 (13)	C13—C14—C9	121.72 (14)
C5—C4—C3	120.01 (14)	C13—C14—H14A	119.1
C5—C4—H4A	120.0	C9—C14—H14A	119.1
C3—C4—H4A	120.0	O8—C15—O7	124.10 (14)
C4—C5—C6	122.65 (13)	O8—C15—C12	123.56 (14)
C4—C5—N1	115.70 (13)	O7—C15—C12	112.33 (13)
C6—C5—N1	121.64 (13)	O7—C16—H16A	109.5
C7—C6—C5	115.81 (13)	O7—C16—H16B	109.5
C7—C6—C9	116.20 (13)	H16A—C16—H16B	109.5
C5—C6—C9	127.81 (13)	O7—C16—H16C	109.5
C8—C7—C6	122.27 (14)	H16A—C16—H16C	109.5
C8—C7—H7A	118.9	H16B—C16—H16C	109.5
C1—O1—C2—O2	3.3 (2)	C7—C6—C9—C10	122.53 (16)
C1—O1—C2—C3	−176.29 (11)	C5—C6—C9—C10	−62.6 (2)
O2—C2—C3—C8	−3.9 (2)	C14—C9—C10—C11	−3.2 (2)
O1—C2—C3—C8	175.74 (12)	C6—C9—C10—C11	179.48 (14)
O2—C2—C3—C4	177.44 (14)	C14—C9—C10—N2	175.83 (13)
O1—C2—C3—C4	−2.96 (19)	C6—C9—C10—N2	−1.5 (2)
C8—C3—C4—C5	−0.1 (2)	O6—N2—C10—C11	−12.78 (19)
C2—C3—C4—C5	178.64 (13)	O5—N2—C10—C11	165.42 (13)
C3—C4—C5—C6	−0.5 (2)	O6—N2—C10—C9	168.14 (13)
C3—C4—C5—N1	−179.15 (12)	O5—N2—C10—C9	−13.7 (2)
O4—N1—C5—C4	170.63 (13)	C9—C10—C11—C12	2.8 (2)
O3—N1—C5—C4	−7.86 (19)	N2—C10—C11—C12	−176.24 (13)
O4—N1—C5—C6	−8.1 (2)	C10—C11—C12—C13	−0.6 (2)
O3—N1—C5—C6	173.45 (13)	C10—C11—C12—C15	178.61 (13)
C4—C5—C6—C7	−0.1 (2)	C11—C12—C13—C14	−1.1 (2)
N1—C5—C6—C7	178.50 (12)	C15—C12—C13—C14	179.67 (13)
C4—C5—C6—C9	−174.94 (13)	C12—C13—C14—C9	0.6 (2)
N1—C5—C6—C9	3.7 (2)	C10—C9—C14—C13	1.4 (2)
C5—C6—C7—C8	1.2 (2)	C6—C9—C14—C13	179.09 (13)
C9—C6—C7—C8	176.70 (13)	C16—O7—C15—O8	2.6 (2)
C4—C3—C8—C7	1.2 (2)	C16—O7—C15—C12	−177.15 (13)
C2—C3—C8—C7	−177.57 (13)	C11—C12—C15—O8	178.12 (15)
C6—C7—C8—C3	−1.8 (2)	C13—C12—C15—O8	−2.7 (2)
C7—C6—C9—C14	−54.82 (18)	C11—C12—C15—O7	−2.1 (2)
C5—C6—C9—C14	120.00 (16)	C13—C12—C15—O7	177.07 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O3i	0.98	2.50	3.253 (2)	134
C1—H1C···O2ii	0.98	2.57	3.5214 (19)	164
C14—H14A···O2iii	0.95	2.47	3.2399 (19)	138
C8—H8A···O3iv	0.95	2.41	3.3239 (19)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O3i	0.98	2.50	3.253 (2)	134
C1—H1C⋯O2ii	0.98	2.57	3.5214 (19)	164
C14—H14A⋯O2iii	0.95	2.47	3.2399 (19)	138
C8—H8A⋯O3iv	0.95	2.41	3.3239 (19)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .