organic compounds
2-[(6-Nitro-1,3-benzodioxol-5-yl)methylidene]malononitrile
aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: ksethusankar@yahoo.co.in
In the title compound, C11H5N3O4, the nitro group is rotated by 29.91 (16)° out of the plane of the adjacent aryl ring. The 1,3-benzodioxole ring is nearly planar, with a maximium deviation of 0.0562 (10) Å. The dioxolene ring adopts an on the O—C—O C atom. In the crystal, molecules are linked via C—H⋯O interactions, resulting in R22(6) and R22(12) graph-set motifs.
Related literature
For applications of malononitrile derivatives, see: Brimblecombe et al. (1972). For related structure, see: Loghmani–Khouzani et al. (2009). For comparison of molecular dimensions, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975). For graph–set motif notations, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al. 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536811049816/rk2314sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049816/rk2314Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811049816/rk2314Isup3.cml
To a solution of malononitrile (0.082 g, 1.24 mmol) in dichloromethane (5 ml), pyrrolidine (0.073 g, 1.03 mmol) was added and stirred well for 10 minutes. To this solution 6–nitrobenzo[d][1,3]dioxole–5–carbaldehyde (0.2 g, 1.03 mmol) was added and stirring was continued for 12 h. After the completion of the reaction as evidenced by TLC, the reaction mixture was poured into 2 N HCl solution (10 ml) and extracted using 25 ml of dichloromethane. The organic layer thus obtained was concentrated under reduced pressure. Column purification (silica gel, mesh size: 60–120) of the crude mixture using 15% ethyl acetate in hexanes successfully provided the desired 2–((6–nitrobenzo[d][1,3]dioxol–5–yl)methylene)malononitrile in 90% yield (0.23 g).
The hydrogen atoms were placed in calculated positions with C—H = 0.93Å to 0.97Å and refined in the riding model with fixed isotropic displacement parameters: Uiso(H) = 1.2Ueq(C) for aromatic and methylene groups.
The malononitrile derivative is used to investigate a variety of possible pharmacological effects when administered by various routes to whole animals and when applied to isolated organs and tissues (Brimblecombe et al., 1972). Also, it is a component of "tear gas" commonly reffered as CS gas, which is used as a riot control agent.
In the title compound C11H5N3O4, the benzodioxole ring is nearly planar with a maximum deviation 0.0562Å for the atom O2. The O═N═O angle is much larger than the ideal tetrahedral or trigonal values, respectively, doubtless as a consequence of the substantial negative charge on the paired O atoms. The bond lengths C9—C10 = 1.4388 (16)Å and C9—C11 = 1.4342 (16)Å is significantly shorter than the expected value for a C—C single bond because of conjugation effects.
In the dioxole ring C1/O2/C2/C7/O1, the deviation of atom C1 is -0.0724 (16)Å. The dioxole ring adopts a φ2 = 36.7 (6)°. The malononitrile group (C9—C10≡N2) and (C9—C11≡N3) is almost linear, with the angle around central carbon atoms C10 and C11 being 179.14 (15)° and 179.09 (15)° respectively.
conformation on C1 with puckering parameters (Cremer & Pople, 1975): Q2 = 0.1145 (13)Å andThe values of the torsion angles C5–C4–C8–C9 = -154.85 (11)° and C4–C5–N1–O4 = -151.10 (12)° indicates that the conformation of molecule is (-)anti–periplanar. The nitro group is not co–planar to the benzodioxole ring to which it is attached, making a dihedral angle of 29.76 (4)°. The benzodioxole unit is oriented at a dihedral angle of 36.90 (4)° with respect to the malononitrile group. The triple bond distances C10≡N2 and C11≡N3 are in agreement with the literature values (1.138 (7)Å; Allen et al., 1987). The title compound exhibits structural similarities with the already reported related structures (Loghmani–Khouzani et al., 2009).
The crystal packing is stabilized by non–classical intermolecular C—H···O interactions. The molecules are linked into centrosymmetric dimers. Atom C1 acts as a donor to dioxole O1i, so forming an R22(6) graph–set motif and atom C8 acts as a donor to nitro group O4ii at forming an R22(12) graph–set motif (Bernstein, et al., 1995). Symmetry codes: (i) -x, 1-y, 2-z; (ii) -1-x, 2-y, 1-z).
For applications of malononitrile derivatives, see: Brimblecombe et al. (1972). For related structure, see: Loghmani–Khouzani et al. (2009). For comparison of molecular dimensions, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975). For graph–set motif notations, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al. 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C11H5N3O4 | Z = 2 |
Mr = 243.18 | F(000) = 248 |
Triclinic, P1 | Dx = 1.532 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0953 (2) Å | Cell parameters from 3494 reflections |
b = 8.8847 (3) Å | θ = 1.0–31.6° |
c = 9.2212 (3) Å | µ = 0.12 mm−1 |
α = 84.470 (2)° | T = 295 K |
β = 67.634 (2)° | Block, yellow |
γ = 78.874 (2)° | 0.30 × 0.28 × 0.25 mm |
V = 527.30 (3) Å3 |
Bruker Kappa APEXII CCD diffractometer | 2700 reflections with I > 2σ(I) |
Radiation source: fine–focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 31.6°, θmin = 2.3° |
ω scans | h = −10→10 |
13806 measured reflections | k = −12→12 |
3494 independent 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0779P)2 + 0.0833P] where P = (Fo2 + 2Fc2)/3 |
3494 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C11H5N3O4 | γ = 78.874 (2)° |
Mr = 243.18 | V = 527.30 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0953 (2) Å | Mo Kα radiation |
b = 8.8847 (3) Å | µ = 0.12 mm−1 |
c = 9.2212 (3) Å | T = 295 K |
α = 84.470 (2)° | 0.30 × 0.28 × 0.25 mm |
β = 67.634 (2)° |
Bruker Kappa APEXII CCD diffractometer | 2700 reflections with I > 2σ(I) |
13806 measured reflections | Rint = 0.025 |
3494 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.28 e Å−3 |
3494 reflections | Δρmin = −0.30 e Å−3 |
163 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | 0.1956 (2) | 0.45131 (18) | 0.79855 (15) | 0.0499 (3) | |
H1A | 0.2553 | 0.3433 | 0.7969 | 0.060* | |
H1B | 0.2182 | 0.4995 | 0.8792 | 0.060* | |
C2 | 0.13009 (16) | 0.60560 (13) | 0.61230 (12) | 0.0335 (2) | |
C3 | 0.13982 (17) | 0.70725 (13) | 0.48999 (12) | 0.0345 (2) | |
H3 | 0.2663 | 0.7286 | 0.4190 | 0.041* | |
C4 | −0.04642 (16) | 0.77900 (12) | 0.47404 (12) | 0.0309 (2) | |
C5 | −0.23081 (16) | 0.74097 (12) | 0.58573 (13) | 0.0331 (2) | |
C6 | −0.24088 (17) | 0.63890 (13) | 0.71134 (13) | 0.0373 (2) | |
H6 | −0.3660 | 0.6171 | 0.7842 | 0.045* | |
C7 | −0.05588 (18) | 0.57270 (13) | 0.72113 (12) | 0.0351 (2) | |
C8 | −0.04545 (17) | 0.90159 (12) | 0.35650 (13) | 0.0347 (2) | |
H8 | −0.1612 | 0.9786 | 0.3818 | 0.042* | |
C9 | 0.10476 (19) | 0.91503 (13) | 0.21576 (14) | 0.0386 (2) | |
C10 | 0.0900 (2) | 1.05218 (15) | 0.12130 (16) | 0.0478 (3) | |
C11 | 0.2814 (2) | 0.79907 (17) | 0.14691 (15) | 0.0491 (3) | |
N1 | −0.42888 (15) | 0.80802 (11) | 0.57275 (13) | 0.0417 (2) | |
N2 | 0.0804 (3) | 1.16093 (16) | 0.04706 (18) | 0.0707 (4) | |
N3 | 0.4220 (2) | 0.7081 (2) | 0.09043 (17) | 0.0760 (5) | |
O1 | −0.02108 (14) | 0.46924 (11) | 0.82958 (10) | 0.0483 (2) | |
O2 | 0.28869 (13) | 0.52328 (11) | 0.64860 (10) | 0.0457 (2) | |
O3 | −0.43369 (15) | 0.84163 (11) | 0.44228 (12) | 0.0507 (3) | |
O4 | −0.58153 (15) | 0.82535 (14) | 0.69255 (14) | 0.0674 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0424 (7) | 0.0658 (8) | 0.0332 (6) | 0.0027 (6) | −0.0132 (5) | 0.0108 (5) |
C2 | 0.0307 (5) | 0.0392 (5) | 0.0288 (5) | −0.0007 (4) | −0.0115 (4) | −0.0001 (4) |
C3 | 0.0298 (5) | 0.0412 (5) | 0.0304 (5) | −0.0058 (4) | −0.0101 (4) | 0.0036 (4) |
C4 | 0.0308 (5) | 0.0307 (5) | 0.0304 (5) | −0.0039 (4) | −0.0114 (4) | 0.0004 (4) |
C5 | 0.0279 (5) | 0.0323 (5) | 0.0367 (5) | −0.0011 (4) | −0.0111 (4) | −0.0009 (4) |
C6 | 0.0306 (5) | 0.0396 (6) | 0.0343 (5) | −0.0040 (4) | −0.0056 (4) | 0.0033 (4) |
C7 | 0.0364 (5) | 0.0372 (5) | 0.0272 (5) | −0.0026 (4) | −0.0094 (4) | 0.0024 (4) |
C8 | 0.0349 (5) | 0.0324 (5) | 0.0388 (5) | −0.0057 (4) | −0.0167 (4) | 0.0030 (4) |
C9 | 0.0410 (6) | 0.0401 (6) | 0.0386 (6) | −0.0114 (5) | −0.0190 (5) | 0.0086 (4) |
C10 | 0.0602 (8) | 0.0460 (7) | 0.0449 (7) | −0.0211 (6) | −0.0253 (6) | 0.0122 (5) |
C11 | 0.0415 (7) | 0.0632 (8) | 0.0361 (6) | −0.0077 (6) | −0.0108 (5) | 0.0109 (5) |
N1 | 0.0309 (5) | 0.0360 (5) | 0.0550 (6) | −0.0031 (4) | −0.0153 (4) | 0.0051 (4) |
N2 | 0.1052 (13) | 0.0544 (7) | 0.0656 (9) | −0.0313 (8) | −0.0436 (9) | 0.0243 (6) |
N3 | 0.0539 (8) | 0.0989 (12) | 0.0516 (8) | 0.0105 (8) | −0.0062 (6) | 0.0049 (8) |
O1 | 0.0414 (5) | 0.0590 (6) | 0.0362 (4) | −0.0034 (4) | −0.0116 (4) | 0.0164 (4) |
O2 | 0.0336 (4) | 0.0603 (6) | 0.0375 (4) | 0.0003 (4) | −0.0141 (3) | 0.0121 (4) |
O3 | 0.0472 (5) | 0.0499 (5) | 0.0639 (6) | −0.0064 (4) | −0.0329 (5) | 0.0056 (4) |
O4 | 0.0323 (5) | 0.0746 (7) | 0.0705 (7) | 0.0072 (5) | −0.0034 (5) | 0.0157 (6) |
C1—O1 | 1.4319 (17) | C5—N1 | 1.4614 (14) |
C1—O2 | 1.4334 (15) | C6—C7 | 1.3635 (15) |
C1—H1A | 0.9700 | C6—H6 | 0.9300 |
C1—H1B | 0.9700 | C7—O1 | 1.3525 (13) |
C2—O2 | 1.3547 (13) | C8—C9 | 1.3420 (16) |
C2—C3 | 1.3641 (15) | C8—H8 | 0.9300 |
C2—C7 | 1.3850 (16) | C9—C11 | 1.4342 (19) |
C3—C4 | 1.4068 (14) | C9—C10 | 1.4388 (16) |
C3—H3 | 0.9300 | C10—N2 | 1.1355 (18) |
C4—C5 | 1.4016 (15) | C11—N3 | 1.138 (2) |
C4—C8 | 1.4597 (14) | N1—O4 | 1.2145 (15) |
C5—C6 | 1.3887 (15) | N1—O3 | 1.2230 (14) |
O1—C1—O2 | 107.04 (9) | C7—C6—H6 | 122.1 |
O1—C1—H1A | 110.3 | C5—C6—H6 | 122.1 |
O2—C1—H1A | 110.3 | O1—C7—C6 | 128.09 (10) |
O1—C1—H1B | 110.3 | O1—C7—C2 | 110.03 (10) |
O2—C1—H1B | 110.3 | C6—C7—C2 | 121.87 (10) |
H1A—C1—H1B | 108.6 | C9—C8—C4 | 126.91 (10) |
O2—C2—C3 | 128.07 (10) | C9—C8—H8 | 116.5 |
O2—C2—C7 | 109.65 (9) | C4—C8—H8 | 116.5 |
C3—C2—C7 | 122.28 (10) | C8—C9—C11 | 124.80 (11) |
C2—C3—C4 | 118.30 (10) | C8—C9—C10 | 119.43 (12) |
C2—C3—H3 | 120.9 | C11—C9—C10 | 115.74 (11) |
C4—C3—H3 | 120.9 | N2—C10—C9 | 179.14 (15) |
C5—C4—C3 | 117.50 (9) | N3—C11—C9 | 179.09 (15) |
C5—C4—C8 | 121.96 (9) | O4—N1—O3 | 123.24 (11) |
C3—C4—C8 | 120.12 (9) | O4—N1—C5 | 118.09 (11) |
C6—C5—C4 | 124.20 (10) | O3—N1—C5 | 118.67 (10) |
C6—C5—N1 | 115.70 (10) | C7—O1—C1 | 105.81 (9) |
C4—C5—N1 | 120.10 (10) | C2—O2—C1 | 105.89 (9) |
C7—C6—C5 | 115.83 (10) | ||
O2—C2—C3—C4 | 179.32 (11) | C3—C2—C7—C6 | 0.79 (18) |
C7—C2—C3—C4 | −0.78 (17) | C5—C4—C8—C9 | −154.85 (11) |
C2—C3—C4—C5 | 0.01 (16) | C3—C4—C8—C9 | 32.75 (16) |
C2—C3—C4—C8 | 172.74 (10) | C4—C8—C9—C11 | 8.72 (19) |
C3—C4—C5—C6 | 0.80 (17) | C4—C8—C9—C10 | −173.31 (10) |
C8—C4—C5—C6 | −171.78 (10) | C6—C5—N1—O4 | 29.91 (16) |
C3—C4—C5—N1 | −178.10 (9) | C4—C5—N1—O4 | −151.10 (12) |
C8—C4—C5—N1 | 9.32 (16) | C6—C5—N1—O3 | −148.95 (11) |
C4—C5—C6—C7 | −0.81 (17) | C4—C5—N1—O3 | 30.04 (15) |
N1—C5—C6—C7 | 178.14 (10) | C6—C7—O1—C1 | −173.03 (12) |
C5—C6—C7—O1 | −179.34 (11) | C2—C7—O1—C1 | 7.55 (14) |
C5—C6—C7—C2 | 0.01 (17) | O2—C1—O1—C7 | −12.15 (14) |
O2—C2—C7—O1 | 0.17 (14) | C3—C2—O2—C1 | 172.11 (12) |
C3—C2—C7—O1 | −179.75 (10) | C7—C2—O2—C1 | −7.80 (14) |
O2—C2—C7—C6 | −179.29 (10) | O1—C1—O2—C2 | 12.26 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···O1i | 0.97 | 2.53 | 3.2692 (16) | 133 |
C8—H8···O4ii | 0.93 | 2.52 | 3.3640 (17) | 152 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x−1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C11H5N3O4 |
Mr | 243.18 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.0953 (2), 8.8847 (3), 9.2212 (3) |
α, β, γ (°) | 84.470 (2), 67.634 (2), 78.874 (2) |
V (Å3) | 527.30 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.30 × 0.28 × 0.25 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13806, 3494, 2700 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.737 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.142, 1.03 |
No. of reflections | 3494 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.30 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al. 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···O1i | 0.97 | 2.53 | 3.2692 (16) | 133 |
C8—H8···O4ii | 0.93 | 2.52 | 3.3640 (17) | 152 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x−1, −y+2, −z+1. |
Acknowledgements
SK and KS thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the
data collection and Dr V. Murugan, Head of the Department of Physics, RKM Vivekananda College, for providing facilities in the department for carrying out this work.References
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The malononitrile derivative is used to investigate a variety of possible pharmacological effects when administered by various routes to whole animals and when applied to isolated organs and tissues (Brimblecombe et al., 1972). Also, it is a component of "tear gas" commonly reffered as CS gas, which is used as a riot control agent.
In the title compound C11H5N3O4, the benzodioxole ring is nearly planar with a maximum deviation 0.0562Å for the atom O2. The O═N═O angle is much larger than the ideal tetrahedral or trigonal values, respectively, doubtless as a consequence of the substantial negative charge on the paired O atoms. The bond lengths C9—C10 = 1.4388 (16)Å and C9—C11 = 1.4342 (16)Å is significantly shorter than the expected value for a C—C single bond because of conjugation effects.
In the dioxole ring C1/O2/C2/C7/O1, the deviation of atom C1 is -0.0724 (16)Å. The dioxole ring adopts a envelope conformation on C1 with puckering parameters (Cremer & Pople, 1975): Q2 = 0.1145 (13)Å and φ2 = 36.7 (6)°. The malononitrile group (C9—C10≡N2) and (C9—C11≡N3) is almost linear, with the angle around central carbon atoms C10 and C11 being 179.14 (15)° and 179.09 (15)° respectively.
The values of the torsion angles C5–C4–C8–C9 = -154.85 (11)° and C4–C5–N1–O4 = -151.10 (12)° indicates that the conformation of molecule is (-)anti–periplanar. The nitro group is not co–planar to the benzodioxole ring to which it is attached, making a dihedral angle of 29.76 (4)°. The benzodioxole unit is oriented at a dihedral angle of 36.90 (4)° with respect to the malononitrile group. The triple bond distances C10≡N2 and C11≡N3 are in agreement with the literature values (1.138 (7)Å; Allen et al., 1987). The title compound exhibits structural similarities with the already reported related structures (Loghmani–Khouzani et al., 2009).
The crystal packing is stabilized by non–classical intermolecular C—H···O interactions. The molecules are linked into centrosymmetric dimers. Atom C1 acts as a donor to dioxole O1i, so forming an R22(6) graph–set motif and atom C8 acts as a donor to nitro group O4ii at forming an R22(12) graph–set motif (Bernstein, et al., 1995). Symmetry codes: (i) -x, 1-y, 2-z; (ii) -1-x, 2-y, 1-z).