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Hexanitrostilbene (HNS) is an energetic material with wide application and excellent comprehensive performance. cis-HNS is successfully prepared using crude HNS with a purity of 95% as the raw material and N-methyl pyrrolidone (NMP) as the solvent. After separation and purification, acetone is used as a solvent to obtain light-yellow crystals at room temperature. The molecular structure of cis-HNS is determined through analysis of Fourier transform infrared, 13C NMR and 1H NMR spectroscopy and single-crystal X-ray diffraction data. The thermal decomposition properties of cis and trans-HNS are studied using differential scanning calorimetry (DSC). When the heating rate is low, cis-HNS will undergo a crystal transformation after melting, from liquid cis-HNS to liquid trans-HNS, and then it will solidify and release heat. According to the results of DSC data, the apparent kinetic parameters of thermal decomposition of cis- and trans-HNS were obtained by Kissinger method [Kissinger (1957). Anal. Chem. 29, 1702–1706] and Ozawa method [Ozawa (1965). Bull. Chem. Soc. Jpn. 38, 1881–1886], respectively. The spontaneous combustion temperature and self-accelerating decomposition temperature of cis and trans-HNS are calculated by the Zhang-Hu-Xie-Li method [Zhang et al. (1994). Thermochim. Acta, 244, 171–176].
Supporting information
CCDC reference: 2017990
Cell refinement: SAINT V8.38A (?, 2016); data reduction: SAINT V8.38A (?, 2016); program(s) used to solve structure: ShelXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
Crystal data top
C14H6N6O12 | F(000) = 1824 |
Mr = 450.25 | Dx = 1.815 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.2210 (6) Å | Cell parameters from 6085 reflections |
b = 10.3080 (3) Å | θ = 2.2–26.3° |
c = 19.4134 (5) Å | µ = 0.16 mm−1 |
β = 129.087 (1)° | T = 170 K |
V = 3296.17 (16) Å3 | Block, colourless |
Z = 8 | 0.15 × 0.08 × 0.05 mm |
Data collection top
D8 VENTURE diffractometer | Rint = 0.088 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0842 before and 0.0479 after correction. The Ratio of minimum to maximum transmission is 0.9408. The λ/2 correction factor is Not present. | θmax = 26.5°, θmin = 2.2° |
Tmin = 0.701, Tmax = 0.745 | h = −26→26 |
17600 measured reflections | k = −12→12 |
3373 independent reflections | l = −24→24 |
2698 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0482P)2 + 3.4414P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3373 reflections | Δρmax = 0.29 e Å−3 |
298 parameters | Δρmin = −0.28 e Å−3 |
301 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O6 | 0.75656 (9) | 0.74827 (14) | 0.40818 (9) | 0.0324 (3) | |
O4 | 0.93226 (9) | 0.79655 (13) | 0.53960 (9) | 0.0317 (3) | |
O7 | 0.91740 (9) | 0.33299 (16) | 0.39913 (10) | 0.0365 (4) | |
O11 | 0.46780 (9) | 0.41969 (15) | 0.14686 (10) | 0.0353 (4) | |
O10 | 0.72633 (10) | 0.53469 (14) | 0.09454 (9) | 0.0334 (4) | |
O12 | 0.47955 (9) | 0.37459 (15) | 0.04638 (9) | 0.0361 (4) | |
O8 | 0.79229 (9) | 0.29173 (14) | 0.34001 (9) | 0.0341 (4) | |
O9 | 0.82602 (9) | 0.45615 (16) | 0.22315 (10) | 0.0362 (4) | |
O1 | 0.83129 (11) | 0.21228 (16) | 0.62521 (12) | 0.0465 (4) | |
O2 | 0.92088 (11) | 0.33393 (18) | 0.73719 (11) | 0.0474 (5) | |
O5 | 0.70945 (11) | 0.58492 (17) | 0.43374 (10) | 0.0442 (4) | |
N4 | 0.50520 (10) | 0.42001 (15) | 0.11851 (11) | 0.0247 (4) | |
N6 | 0.85907 (10) | 0.33946 (15) | 0.39724 (10) | 0.0243 (4) | |
N5 | 0.75780 (10) | 0.50229 (15) | 0.17035 (11) | 0.0241 (4) | |
N2 | 0.93302 (10) | 0.72497 (16) | 0.58937 (10) | 0.0286 (4) | |
N3 | 0.72232 (10) | 0.64347 (16) | 0.38901 (10) | 0.0249 (4) | |
N1 | 0.87753 (12) | 0.30498 (18) | 0.65845 (13) | 0.0344 (4) | |
C11 | 0.61741 (11) | 0.52981 (17) | 0.25466 (12) | 0.0205 (4) | |
H11 | 0.586001 | 0.532172 | 0.274032 | 0.025* | |
C12 | 0.58702 (11) | 0.47618 (17) | 0.17417 (12) | 0.0207 (4) | |
C13 | 0.63158 (11) | 0.47012 (17) | 0.14458 (12) | 0.0210 (4) | |
H13 | 0.609220 | 0.435334 | 0.088014 | 0.025* | |
C9 | 0.74601 (11) | 0.57442 (16) | 0.28371 (11) | 0.0180 (4) | |
O3 | 0.9443 (2) | 0.7628 (4) | 0.6570 (2) | 0.0451 (9) | 0.75 |
C8 | 0.82967 (11) | 0.62663 (17) | 0.33614 (11) | 0.0198 (4) | |
H8 | 0.840302 | 0.676894 | 0.303456 | 0.024* | |
C4 | 0.86181 (11) | 0.32986 (19) | 0.52342 (12) | 0.0241 (4) | |
H4 | 0.843144 | 0.242830 | 0.507686 | 0.029* | |
C1 | 0.91002 (11) | 0.58709 (18) | 0.56482 (12) | 0.0216 (4) | |
C7 | 0.89197 (11) | 0.61363 (17) | 0.42198 (11) | 0.0202 (4) | |
H7 | 0.940985 | 0.656821 | 0.443962 | 0.024* | |
C6 | 0.89143 (10) | 0.53722 (18) | 0.48651 (11) | 0.0198 (4) | |
C14 | 0.70953 (11) | 0.51666 (17) | 0.20068 (11) | 0.0193 (4) | |
C10 | 0.69528 (11) | 0.58025 (17) | 0.30650 (11) | 0.0193 (4) | |
C5 | 0.87004 (11) | 0.40667 (18) | 0.47128 (12) | 0.0212 (4) | |
C3 | 0.88205 (12) | 0.38592 (19) | 0.59942 (13) | 0.0259 (4) | |
C2 | 0.90706 (12) | 0.51313 (19) | 0.62216 (12) | 0.0255 (4) | |
H2 | 0.921819 | 0.548945 | 0.675650 | 0.031* | |
O0AA | 0.9790 (6) | 0.7473 (12) | 0.6695 (6) | 0.041 (3) | 0.25 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O6 | 0.0381 (8) | 0.0240 (7) | 0.0343 (8) | −0.0032 (6) | 0.0224 (7) | −0.0083 (6) |
O4 | 0.0421 (9) | 0.0257 (7) | 0.0292 (7) | −0.0052 (6) | 0.0234 (7) | −0.0019 (6) |
O7 | 0.0318 (8) | 0.0469 (9) | 0.0353 (8) | 0.0099 (7) | 0.0232 (7) | −0.0007 (7) |
O11 | 0.0278 (8) | 0.0429 (9) | 0.0433 (9) | −0.0099 (6) | 0.0264 (7) | −0.0095 (7) |
O10 | 0.0515 (10) | 0.0333 (8) | 0.0302 (8) | −0.0017 (7) | 0.0328 (8) | 0.0008 (6) |
O12 | 0.0286 (8) | 0.0453 (9) | 0.0297 (8) | −0.0136 (7) | 0.0162 (7) | −0.0141 (7) |
O8 | 0.0333 (8) | 0.0267 (7) | 0.0316 (8) | −0.0083 (6) | 0.0154 (7) | −0.0080 (6) |
O9 | 0.0230 (8) | 0.0547 (10) | 0.0340 (8) | −0.0040 (7) | 0.0195 (7) | −0.0104 (7) |
O1 | 0.0479 (10) | 0.0393 (9) | 0.0728 (12) | 0.0085 (8) | 0.0478 (10) | 0.0213 (8) |
O2 | 0.0672 (12) | 0.0524 (10) | 0.0434 (10) | 0.0200 (9) | 0.0447 (10) | 0.0196 (8) |
O5 | 0.0562 (11) | 0.0589 (11) | 0.0342 (8) | −0.0159 (9) | 0.0364 (8) | −0.0094 (8) |
N4 | 0.0220 (8) | 0.0239 (8) | 0.0277 (8) | −0.0021 (7) | 0.0154 (7) | −0.0016 (7) |
N6 | 0.0268 (9) | 0.0190 (8) | 0.0256 (8) | 0.0038 (7) | 0.0157 (7) | 0.0016 (6) |
N5 | 0.0297 (9) | 0.0242 (8) | 0.0263 (8) | −0.0077 (7) | 0.0214 (8) | −0.0076 (7) |
N2 | 0.0310 (9) | 0.0304 (9) | 0.0194 (8) | −0.0026 (7) | 0.0135 (7) | −0.0043 (7) |
N3 | 0.0259 (8) | 0.0289 (9) | 0.0234 (8) | 0.0010 (7) | 0.0172 (7) | −0.0032 (7) |
N1 | 0.0398 (10) | 0.0353 (10) | 0.0472 (11) | 0.0182 (9) | 0.0365 (10) | 0.0184 (9) |
C11 | 0.0224 (9) | 0.0194 (9) | 0.0243 (9) | 0.0017 (7) | 0.0168 (8) | 0.0019 (7) |
C12 | 0.0192 (9) | 0.0189 (9) | 0.0216 (9) | −0.0009 (7) | 0.0117 (8) | 0.0015 (7) |
C13 | 0.0235 (9) | 0.0192 (9) | 0.0181 (9) | −0.0020 (7) | 0.0121 (8) | −0.0001 (7) |
C9 | 0.0205 (9) | 0.0157 (8) | 0.0183 (8) | 0.0003 (7) | 0.0124 (7) | 0.0028 (7) |
O3 | 0.066 (2) | 0.0404 (16) | 0.0294 (15) | −0.0062 (19) | 0.0304 (18) | −0.0113 (12) |
C8 | 0.0246 (9) | 0.0183 (8) | 0.0220 (9) | −0.0050 (7) | 0.0174 (8) | −0.0021 (7) |
C4 | 0.0193 (9) | 0.0217 (9) | 0.0317 (10) | 0.0042 (7) | 0.0163 (8) | 0.0049 (8) |
C1 | 0.0195 (9) | 0.0233 (9) | 0.0203 (9) | 0.0004 (7) | 0.0118 (8) | 0.0002 (7) |
C7 | 0.0210 (9) | 0.0209 (9) | 0.0215 (9) | −0.0040 (7) | 0.0147 (8) | −0.0035 (7) |
C6 | 0.0148 (8) | 0.0243 (9) | 0.0191 (8) | 0.0018 (7) | 0.0101 (7) | 0.0009 (7) |
C14 | 0.0242 (9) | 0.0187 (9) | 0.0206 (9) | −0.0014 (7) | 0.0168 (8) | 0.0002 (7) |
C10 | 0.0231 (9) | 0.0170 (8) | 0.0172 (8) | 0.0018 (7) | 0.0124 (8) | 0.0011 (7) |
C5 | 0.0182 (9) | 0.0240 (9) | 0.0210 (9) | 0.0029 (7) | 0.0122 (7) | 0.0002 (7) |
C3 | 0.0254 (10) | 0.0301 (10) | 0.0312 (10) | 0.0100 (8) | 0.0222 (9) | 0.0115 (8) |
C2 | 0.0241 (10) | 0.0321 (10) | 0.0213 (9) | 0.0072 (8) | 0.0148 (8) | 0.0039 (8) |
O0AA | 0.058 (6) | 0.036 (5) | 0.022 (3) | −0.014 (5) | 0.022 (4) | −0.011 (3) |
Geometric parameters (Å, º) top
O6—N3 | 1.222 (2) | C11—C12 | 1.376 (2) |
O4—N2 | 1.208 (2) | C11—C10 | 1.384 (3) |
O7—N6 | 1.217 (2) | C12—C13 | 1.383 (3) |
O11—N4 | 1.218 (2) | C13—H13 | 0.9500 |
O10—N5 | 1.218 (2) | C13—C14 | 1.371 (3) |
O12—N4 | 1.231 (2) | C9—C8 | 1.483 (2) |
O8—N6 | 1.224 (2) | C9—C14 | 1.407 (2) |
O9—N5 | 1.225 (2) | C9—C10 | 1.400 (2) |
O1—N1 | 1.222 (3) | C8—H8 | 0.9500 |
O2—N1 | 1.224 (2) | C8—C7 | 1.328 (3) |
O5—N3 | 1.221 (2) | C4—H4 | 0.9500 |
N4—C12 | 1.467 (2) | C4—C5 | 1.380 (3) |
N6—C5 | 1.476 (2) | C4—C3 | 1.377 (3) |
N5—C14 | 1.476 (2) | C1—C6 | 1.405 (2) |
N2—O3 | 1.240 (4) | C1—C2 | 1.383 (3) |
N2—C1 | 1.481 (2) | C7—H7 | 0.9500 |
N2—O0AA | 1.229 (9) | C7—C6 | 1.486 (2) |
N3—C10 | 1.470 (2) | C6—C5 | 1.391 (3) |
N1—C3 | 1.469 (2) | C3—C2 | 1.379 (3) |
C11—H11 | 0.9500 | C2—H2 | 0.9500 |
| | | |
O11—N4—O12 | 124.49 (16) | C10—C9—C14 | 113.78 (16) |
O11—N4—C12 | 118.30 (15) | C9—C8—H8 | 115.2 |
O12—N4—C12 | 117.20 (15) | C7—C8—C9 | 129.67 (16) |
O7—N6—O8 | 125.36 (16) | C7—C8—H8 | 115.2 |
O7—N6—C5 | 117.61 (15) | C5—C4—H4 | 121.7 |
O8—N6—C5 | 117.00 (15) | C3—C4—H4 | 121.7 |
O10—N5—O9 | 125.16 (16) | C3—C4—C5 | 116.54 (18) |
O10—N5—C14 | 117.68 (16) | C6—C1—N2 | 120.67 (16) |
O9—N5—C14 | 117.14 (15) | C2—C1—N2 | 116.30 (16) |
O4—N2—O3 | 123.5 (3) | C2—C1—C6 | 123.02 (17) |
O4—N2—C1 | 119.57 (15) | C8—C7—H7 | 117.3 |
O4—N2—O0AA | 119.9 (6) | C8—C7—C6 | 125.48 (17) |
O3—N2—C1 | 116.6 (3) | C6—C7—H7 | 117.3 |
O0AA—N2—C1 | 115.1 (6) | C1—C6—C7 | 124.89 (16) |
O6—N3—C10 | 118.21 (15) | C5—C6—C1 | 114.53 (16) |
O5—N3—O6 | 125.23 (16) | C5—C6—C7 | 120.57 (16) |
O5—N3—C10 | 116.55 (16) | C13—C14—N5 | 116.17 (15) |
O1—N1—O2 | 124.80 (18) | C13—C14—C9 | 125.09 (16) |
O1—N1—C3 | 117.25 (19) | C9—C14—N5 | 118.73 (16) |
O2—N1—C3 | 117.94 (19) | C11—C10—N3 | 115.19 (15) |
C12—C11—H11 | 121.1 | C11—C10—C9 | 123.88 (16) |
C12—C11—C10 | 117.81 (16) | C9—C10—N3 | 120.93 (16) |
C10—C11—H11 | 121.1 | C4—C5—N6 | 115.45 (16) |
C11—C12—N4 | 119.00 (16) | C4—C5—C6 | 125.06 (17) |
C11—C12—C13 | 122.43 (17) | C6—C5—N6 | 119.41 (16) |
C13—C12—N4 | 118.54 (16) | C4—C3—N1 | 117.90 (18) |
C12—C13—H13 | 121.5 | C4—C3—C2 | 122.63 (17) |
C14—C13—C12 | 116.90 (16) | C2—C3—N1 | 119.46 (18) |
C14—C13—H13 | 121.5 | C1—C2—H2 | 121.0 |
C14—C9—C8 | 119.73 (15) | C3—C2—C1 | 118.05 (17) |
C10—C9—C8 | 126.44 (15) | C3—C2—H2 | 121.0 |
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