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organic compounds
| CRYSTALLOGRAPHIC COMMUNICATIONS |
access3,3′,5,5′-Tetranitrobiphenyl
aUniversity of Mississippi, Department of Medicinal Chemistry, 417 Faser Hall, University, MS 38677, USA, bNational Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA, and cDepartment of Chemistry and Biochemistry, University of Mississippi, University, MS 38677, USA
*Correspondence e-mail: mavery@olemiss.edu
The title compound, C12H6N4O8, is a biphenyl system that was synthesized as a building block for a new series of antimalarial compounds. The aromatic rings are oriented at a dihedral angle of 45.5 (2)°, and intermolecular short O⋯O contacts form a chain along the b axis. The strength of the interactions involved in this chain cause one of the rings to be slightly distorted, with the torsion angle between the nitro groups being 23.4 (2)°, whereas, in the other ring, both nitro systems are parallel, forming an angle of 9.6 (2)° with the plane of the aromatic ring to which they are bound. Furthermore, the three ring C atoms around the ring–ring linkage belong to a plane inclined by 4.5 (1)° in relation to the plane containing the other three C atoms, i.e. (NO2–)C—C—C(NO2). This distortion of the ring causes uncommonly short intermolecular O⋯O [3.038 (2) Å] and O⋯C [3.000 (4) and 3.214 (1) Å] contacts.
Related literature
For the previous synthesis of the title compound and its stability studies, see Case (1942![[Case, F. H. (1942). J. Am. Chem. Soc. 64, 1848-1852.]](../../../../../../logos/arrows/e_arr.gif "Case, F. H. (1942). J. Am. Chem. Soc. 64, 1848-1852.")
) and Hoffsommer & McCullough (1968). For the use of polynitroaromatic compounds as explosives, see Davis (1941) and Keshavarz & Pouretedal (2005). For their mutagenic and carcinogenic properties, see Debnath et al. (1991). For previous studies showing distortions induced in aromatic rings, see Murray-Rust (1982), Allen et al. (1998), and Khrustalev et al. (2005). For the preparation, see: Goossen et al. (2007).
![[Scheme 1]](im2105scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2008); cell 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.
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536809011088/im2105sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536809011088/im2105Isup2.hkl
The title compound was prepared by decarboxylative coupling as previously published (Goossen et al., 2007). Briefly, 1-bromo-3,5-dinitrobenzene (247 mg, 1 mmol), 3,5-dinitrobenzoic acid (211 mg, 1 mmol), copper(II) bromide (180 mg, 0.8 mmol), 1,2-dimethoxyethane (3 ml), [tetrakis(triphenylphosphine)palladium(0)] (100 mg, 0.086 mmol), [dichlorobis(triphenylphospine)palladium (II)] (60 mg, 0.86 mmol), potassium carbonate (495 mg, 3 mmol) and water (1 ml) were added together in a microwave vial and microwaved at 160°C for 30 minutes while stirring, in a Biotage InitiatorTM Sixty, with variable microwave output. To keep the programmed temperature, the initial output was 100 W for 5 minutes, then varying between 0 and 30 W for the next 25 minutes. The reaction mixture was shaken 3 times with water, then brine and dried over magnesium sulfate and concentrated. The resulting residue was purified by on silica gel, eluting with ethyl acetate/hexanes (90:10) to afford 62 mg (20% yield) of the title compound. 3,3',5,5'-Tetranitrobiphenyl was recrystallized from MeOH:CHCl3 (5:95) by slow evaporation of the solvent at room temperature.
All H atoms were located in difference maps, and treated as riding atoms, except H2' (C—H = 0.95 Å) and H4' (C—H = 0.94 Å), with the following distance restraints: C—H = 0.93 Å, Uiso=1.2Ueq (C) for Csp2.
Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008).
![[Figure 1]](./im2105fig1thm.gif) | Fig. 1. Molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./im2105fig2thm.gif) | Fig. 2. Partial view of the crystal packing of the title compound viewed along the b axis, showing molecules linked into chains by short intermolecular O1'···O4' interactions. |
| C12H6N4O8 | Dx = 1.745 Mg m−3 |
| Mr = 334.21 | Melting point: not measured K |
| Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54178 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 9828 reflections |
| a = 10.0683 (1) Å | θ = 3.9–67.6° |
| b = 15.4640 (2) Å | µ = 1.32 mm−1 |
| c = 16.3436 (2) Å | T = 100 K |
| V = 2544.64 (5) Å3 | Block, yellow |
| Z = 8 | 0.18 × 0.15 × 0.11 mm |
| F(000) = 1360 |
| Bruker APEXII CCD diffractometer | 2294 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.021 |
| Graphite monochromator | θmax = 68.0°, θmin = 5.4° |
| ϕ and ω scans | h = −12→12 |
| 30954 measured reflections | k = −18→18 |
| 2315 independent reflections | l = −19→19 |
| 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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.09 | w = 1/[σ2(Fo2) + (0.0431P)2 + 1.2464P] where P = (Fo2 + 2Fc2)/3 |
| 2315 reflections | (Δ/σ)max < 0.001 |
| 225 parameters | Δρmax = 0.22 e Å−3 |
| 0 restraints | Δρmin = −0.31 e Å−3 |
| 0 constraints |
| C12H6N4O8 | V = 2544.64 (5) Å3 |
| Mr = 334.21 | Z = 8 |
| Orthorhombic, Pbca | Cu Kα radiation |
| a = 10.0683 (1) Å | µ = 1.32 mm−1 |
| b = 15.4640 (2) Å | T = 100 K |
| c = 16.3436 (2) Å | 0.18 × 0.15 × 0.11 mm |
| Bruker APEXII CCD diffractometer | 2294 reflections with I > 2σ(I) |
| 30954 measured reflections | Rint = 0.021 |
| 2315 independent reflections |
| R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
| wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.09 | Δρmax = 0.22 e Å−3 |
| 2315 reflections | Δρmin = −0.31 e Å−3 |
| 225 parameters |
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 | ||
| C1 | 0.34665 (12) | 0.30780 (8) | 0.43269 (7) | 0.0157 (3) | |
| C2 | 0.33233 (12) | 0.30138 (8) | 0.51737 (7) | 0.0156 (3) | |
| H2 | 0.2894 | 0.3448 | 0.5466 | 0.019* | |
| C3 | 0.38272 (12) | 0.22966 (8) | 0.55741 (7) | 0.0162 (3) | |
| C4 | 0.44841 (12) | 0.16333 (8) | 0.51778 (8) | 0.0168 (3) | |
| H4 | 0.4828 | 0.1160 | 0.5458 | 0.020* | |
| C5 | 0.45990 (12) | 0.17162 (8) | 0.43369 (8) | 0.0165 (3) | |
| C6 | 0.41093 (12) | 0.24155 (8) | 0.39006 (7) | 0.0162 (3) | |
| H6 | 0.4206 | 0.2443 | 0.3335 | 0.019* | |
| N1 | 0.37026 (10) | 0.22503 (7) | 0.64699 (6) | 0.0182 (2) | |
| N2 | 0.52978 (10) | 0.10245 (7) | 0.38839 (7) | 0.0189 (2) | |
| O1 | 0.30268 (11) | 0.28031 (6) | 0.68111 (5) | 0.0259 (2) | |
| O2 | 0.42893 (10) | 0.16675 (6) | 0.68273 (5) | 0.0236 (2) | |
| O3 | 0.58781 (10) | 0.04674 (6) | 0.42849 (6) | 0.0276 (2) | |
| O4 | 0.52572 (10) | 0.10442 (6) | 0.31365 (6) | 0.0253 (2) | |
| C1' | 0.30389 (12) | 0.38719 (8) | 0.38844 (7) | 0.0155 (3) | |
| C2' | 0.33837 (12) | 0.46789 (8) | 0.42007 (7) | 0.0162 (3) | |
| H2' | 0.3828 (15) | 0.4741 (10) | 0.4712 (9) | 0.018 (4)* | |
| C3' | 0.31428 (12) | 0.54092 (8) | 0.37355 (7) | 0.0156 (3) | |
| C4' | 0.25353 (12) | 0.53897 (8) | 0.29759 (7) | 0.0159 (3) | |
| H4' | 0.2391 (15) | 0.5895 (9) | 0.2666 (9) | 0.018 (4)* | |
| C5' | 0.21448 (12) | 0.45823 (8) | 0.27031 (7) | 0.0160 (3) | |
| C6' | 0.23899 (12) | 0.38234 (8) | 0.31302 (7) | 0.0161 (3) | |
| H6' | 0.2127 | 0.3292 | 0.2918 | 0.019* | |
| N1' | 0.36202 (10) | 0.62466 (7) | 0.40437 (6) | 0.0169 (2) | |
| N2' | 0.14792 (10) | 0.45304 (7) | 0.18984 (6) | 0.0177 (2) | |
| O1' | 0.38516 (9) | 0.63076 (6) | 0.47790 (5) | 0.0231 (2) | |
| O2' | 0.37639 (9) | 0.68355 (6) | 0.35486 (6) | 0.0212 (2) | |
| O3' | 0.12418 (9) | 0.52096 (6) | 0.15399 (5) | 0.0233 (2) | |
| O4' | 0.12047 (10) | 0.38108 (6) | 0.16341 (6) | 0.0246 (2) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0138 (6) | 0.0161 (6) | 0.0173 (6) | −0.0029 (5) | −0.0013 (4) | 0.0007 (5) |
| C2 | 0.0155 (6) | 0.0143 (6) | 0.0171 (6) | −0.0015 (5) | 0.0002 (5) | −0.0013 (5) |
| C3 | 0.0170 (6) | 0.0179 (6) | 0.0137 (6) | −0.0044 (5) | −0.0009 (4) | 0.0009 (5) |
| C4 | 0.0162 (6) | 0.0149 (6) | 0.0193 (6) | −0.0018 (5) | −0.0024 (5) | 0.0028 (5) |
| C5 | 0.0148 (6) | 0.0154 (6) | 0.0192 (6) | −0.0021 (5) | 0.0010 (5) | −0.0025 (5) |
| C6 | 0.0163 (6) | 0.0183 (6) | 0.0140 (6) | −0.0035 (5) | −0.0005 (4) | −0.0003 (5) |
| N1 | 0.0214 (5) | 0.0174 (5) | 0.0158 (5) | −0.0039 (4) | 0.0003 (4) | 0.0015 (4) |
| N2 | 0.0167 (5) | 0.0169 (5) | 0.0230 (6) | −0.0012 (4) | 0.0017 (4) | −0.0019 (4) |
| O1 | 0.0409 (6) | 0.0193 (5) | 0.0175 (5) | 0.0015 (4) | 0.0061 (4) | −0.0017 (4) |
| O2 | 0.0248 (5) | 0.0269 (5) | 0.0191 (5) | 0.0004 (4) | −0.0015 (4) | 0.0084 (4) |
| O3 | 0.0309 (5) | 0.0200 (5) | 0.0320 (5) | 0.0079 (4) | 0.0017 (4) | 0.0022 (4) |
| O4 | 0.0263 (5) | 0.0304 (5) | 0.0193 (5) | 0.0025 (4) | 0.0033 (4) | −0.0057 (4) |
| C1' | 0.0137 (6) | 0.0173 (6) | 0.0155 (6) | 0.0000 (4) | 0.0026 (4) | 0.0011 (5) |
| C2' | 0.0146 (6) | 0.0194 (6) | 0.0147 (6) | 0.0005 (5) | 0.0003 (5) | 0.0008 (5) |
| C3' | 0.0138 (6) | 0.0154 (6) | 0.0177 (6) | −0.0008 (4) | 0.0017 (5) | −0.0011 (5) |
| C4' | 0.0138 (5) | 0.0173 (6) | 0.0166 (6) | 0.0018 (5) | 0.0024 (5) | 0.0030 (5) |
| C5' | 0.0133 (6) | 0.0206 (6) | 0.0141 (6) | 0.0006 (5) | 0.0001 (4) | 0.0007 (5) |
| C6' | 0.0154 (6) | 0.0164 (6) | 0.0165 (6) | −0.0005 (5) | 0.0021 (5) | −0.0004 (5) |
| N1' | 0.0144 (5) | 0.0172 (5) | 0.0192 (5) | 0.0008 (4) | −0.0004 (4) | 0.0003 (4) |
| N2' | 0.0165 (5) | 0.0211 (5) | 0.0155 (5) | 0.0003 (4) | −0.0004 (4) | 0.0013 (4) |
| O1' | 0.0283 (5) | 0.0236 (5) | 0.0175 (5) | −0.0042 (4) | −0.0031 (4) | −0.0022 (4) |
| O2' | 0.0246 (5) | 0.0154 (4) | 0.0236 (5) | −0.0015 (4) | −0.0009 (4) | 0.0042 (4) |
| O3' | 0.0274 (5) | 0.0222 (5) | 0.0205 (5) | 0.0013 (4) | −0.0059 (4) | 0.0063 (4) |
| O4' | 0.0314 (5) | 0.0213 (5) | 0.0210 (5) | −0.0028 (4) | −0.0074 (4) | −0.0024 (4) |
| C1—C1' | 1.4885 (17) | C5'—N2' | 1.4783 (16) |
| C1'—C2' | 1.3947 (17) | C5—N2 | 1.4790 (16) |
| C1'—C6' | 1.3971 (18) | C6—C1 | 1.3978 (17) |
| C2—C1 | 1.3950 (17) | C6—C5 | 1.3860 (17) |
| C2—C3 | 1.3842 (17) | C6—H6 | 0.9300 |
| C2—H2 | 0.9300 | C6'—H6' | 0.9300 |
| C2'—H2' | 0.953 (15) | N1'—C3' | 1.4702 (15) |
| C3'—C2' | 1.3828 (17) | N1—O1 | 1.2266 (14) |
| C3—C4 | 1.3816 (18) | N1'—O1' | 1.2278 (14) |
| C3—N1 | 1.4712 (15) | N1—O2 | 1.2257 (14) |
| C4'—C3' | 1.3843 (17) | N1'—O2' | 1.2268 (14) |
| C4—H4 | 0.9300 | N2'—O3' | 1.2263 (14) |
| C4'—H4' | 0.942 (15) | N2—O3 | 1.2301 (14) |
| C5'—C4' | 1.3828 (17) | N2—O4 | 1.2226 (15) |
| C5—C4 | 1.3851 (18) | N2'—O4' | 1.2252 (14) |
| C5'—C6' | 1.3876 (17) | ||
| C1—C2—H2 | 120.4 | C4—C5—N2 | 118.00 (11) |
| C1'—C2'—H2' | 122.1 (9) | C5'—C4'—C3' | 115.76 (11) |
| C1'—C6'—H6' | 120.6 | C5—C4—H4 | 122.1 |
| C1—C6—H6 | 120.7 | C5'—C4'—H4' | 122.1 (9) |
| C2'—C1'—C1 | 119.08 (11) | C5—C6—C1 | 118.69 (11) |
| C2—C1—C1' | 120.71 (11) | C5'—C6'—C1' | 118.79 (11) |
| C2—C1—C6 | 119.36 (11) | C5'—C6'—H6' | 120.6 |
| C2'—C1'—C6' | 119.44 (11) | C5—C6—H6 | 120.7 |
| C2'—C3'—C4' | 123.55 (11) | C6—C1—C1' | 119.75 (11) |
| C2'—C3'—N1' | 118.27 (11) | C6'—C1'—C1 | 121.31 (11) |
| C2—C3—N1 | 118.57 (11) | C6—C5—N2 | 118.42 (11) |
| C3'—C2'—C1' | 118.90 (11) | C6'—C5'—N2' | 118.84 (11) |
| C3—C2—C1 | 119.21 (11) | O1'—N1'—C3' | 117.71 (10) |
| C3'—C2'—H2' | 118.9 (9) | O1—N1—C3 | 117.76 (10) |
| C3—C2—H2 | 120.4 | O2'—N1'—C3' | 117.81 (10) |
| C3—C4—C5 | 115.88 (11) | O2—N1—C3 | 117.96 (10) |
| C3—C4—H4 | 122.1 | O2—N1—O1 | 124.27 (10) |
| C3'—C4'—H4' | 122.2 (9) | O2'—N1'—O1' | 124.48 (11) |
| C4—C3—C2 | 123.28 (11) | O3—N2—C5 | 117.76 (10) |
| C4'—C3'—N1' | 118.09 (10) | O3'—N2'—C5' | 117.84 (10) |
| C4—C3—N1 | 118.11 (11) | O4'—N2'—C5' | 117.72 (10) |
| C4'—C5'—C6' | 123.42 (11) | O4—N2—C5 | 117.79 (10) |
| C4—C5—C6 | 123.57 (11) | O4'—N2'—O3' | 124.44 (10) |
| C4'—C5'—N2' | 117.70 (10) | O4—N2—O3 | 124.45 (11) |
| C1—C1'—C2'—C3' | 171.43 (11) | C5'—C4'—C3'—C2' | 1.28 (18) |
| C1—C1'—C6'—C5' | −172.98 (11) | C5'—C4'—C3'—N1' | 177.92 (10) |
| C1—C2—C3—C4 | 0.57 (18) | C5—C6—C1—C1' | 174.55 (11) |
| C1—C2—C3—N1 | 178.25 (11) | C5—C6—C1—C2 | −0.67 (17) |
| C1—C6—C5—C4 | 0.20 (18) | C6—C1—C1'—C2' | −129.65 (12) |
| C1—C6—C5—N2 | −178.99 (10) | C6—C1—C1'—C6' | 45.44 (17) |
| C2—C1—C1'—C2' | 45.51 (17) | C6'—C1'—C2'—C3' | −3.76 (18) |
| C2—C1—C1'—C6' | −139.40 (12) | C6—C5—C4—C3 | 0.62 (18) |
| C2'—C1'—C6'—C5' | 2.09 (18) | C6'—C5'—C4'—C3' | −3.07 (18) |
| C2—C3—C4—C5 | −1.01 (18) | C6—C5—N2—O3 | 170.62 (11) |
| C2—C3—N1—O1 | 7.99 (17) | C6'—C5'—N2'—O3' | 178.23 (11) |
| C2—C3—N1—O2 | −171.36 (11) | C6'—C5'—N2'—O4' | −1.94 (17) |
| C3—C2—C1—C1' | −174.87 (11) | C6—C5—N2—O4 | −9.53 (16) |
| C3—C2—C1—C6 | 0.31 (18) | N1'—C3'—C2'—C1' | −174.56 (11) |
| C4'—C3'—C2'—C1' | 2.08 (19) | N1—C3—C4—C5 | −178.70 (10) |
| C4—C3—N1—O1 | −174.20 (11) | N2'—C5'—C4'—C3' | 179.39 (10) |
| C4—C3—N1—O2 | 6.44 (16) | N2—C5—C4—C3 | 179.81 (10) |
| C4'—C5'—C6'—C1' | 1.44 (19) | N2'—C5'—C6'—C1' | 178.95 (10) |
| C4'—C5'—N2'—O3' | −4.12 (16) | O1'—N1'—C3'—C2' | −20.79 (16) |
| C4—C5—N2—O3 | −8.62 (16) | O1'—N1'—C3'—C4' | 162.39 (11) |
| C4—C5—N2—O4 | 171.23 (11) | O2'—N1'—C3'—C2' | 158.99 (11) |
| C4'—C5'—N2'—O4' | 175.71 (11) | O2'—N1'—C3'—C4' | −17.83 (16) |
Experimental details
| Crystal data | |
| Chemical formula | C12H6N4O8 |
| Mr | 334.21 |
| Crystal system, space group | Orthorhombic, Pbca |
| Temperature (K) | 100 |
| a, b, c (Å) | 10.0683 (1), 15.4640 (2), 16.3436 (2) |
| V (Å3) | 2544.64 (5) |
| Z | 8 |
| Radiation type | Cu Kα |
| µ (mm−1) | 1.32 |
| Crystal size (mm) | 0.18 × 0.15 × 0.11 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD diffractometer |
| Absorption correction | – |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 30954, 2315, 2294 |
| Rint | 0.021 |
| (sin θ/λ)max (Å−1) | 0.601 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.081, 1.09 |
| No. of reflections | 2315 |
| No. of parameters | 225 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.22, −0.31 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The authors thank the Center for Disease Control and Prevention, USA, for providing financial assistance (CDC cooperative agreements 1UO1 CI000211-03 and 1UO1 CI000362-01). This investigation was conducted in a facility constructed with support from Research Facilities Improvement Program grant No. C06Rr-14503-01 from the National Center for Research Resources, National Institutes of Health.
References
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Synthesis of the 3,3',5,5'-tetranitrobiphenyl has previously been reported by Case (1942), from the reaction of 3,5-dinitroiodobenzene and copper at 270°C. This paper reports the crystal structure of the title compound, obtained by reaction of 1-bromo-3,5-dinitrobenzene and 3,5-dinitrobenzoic acid in a sealed microwave tube in 1,2-dimethoxyethane. It was found to have activity against Plasmodium falciparum with an IC50 of 5.7 µM against the chloroquine resistant D6 clone and 3.9µM against the W2 clone.