In the crystal of the title molecular salt, the pyridinium cation and the 3-hydroxy-2,4,6-trinitrophenolate anion are linked through bifurcated N—H⋯(O,O) hydrogen bonds forming an 
(6) ring motif. Impact, friction sensitivity tests and TGA/DTA studies on this compound imply that it is an insensitive high-energy-density material.
Keywords: crystal structure, pyridinium, styphnate, TGA/DTA studies, hydrogen bonding
Abstract
In the crystal structure of the title molecular salt, C5H6N+·C6H2N3O8 − (systematic name: pyridinium 3-hydroxy-2,4,6-trinitrophenolate), the pyridinium cation and the 3-hydroxy-2,4,6-trinitrophenolate anion are linked through bifurcated N—H⋯(O,O) hydrogen bonds, forming an R 1 2(6) ring motif. The nitro group para with respect to phenolate ion forms an intramolecular hydrogen bond with the adjacent phenolic –OH group, which results in an S(6) ring motif. The nitro group flanked by the phenolate ion and the phenolic –OH group deviates noticeably from the benzene ring, subtending a dihedral angle of 89.2 (4)°. The other two nitro groups deviate only slightly from the plane of the benzene ring, making dihedral angles of 2.8 (4) and 3.4 (3)°. In the crystal, the 3-hydroxy-2,4,6-trinitrophenolate anions are linked through O—H⋯O hydrogen bonds, forming chains along [100]. These anionic chains, to which the cations are attached, are linked via C—H⋯O hydrogen bonds, forming a three-dimensional structure. Impact friction sensitivity tests and TGA/DTA studies on the title molecular salt imply that it is an insensitive high-energy-density material.
Chemical context
A number of crystalline styphnate salts with inorganic metal cations have been reported in recent years (Cui et al., 2008a
▸,b
▸; Hu et al., 2005 ▸; Liu et al., 2009 ▸; Orbovic & Codoceo, 2008 ▸; Zhang et al., 2011a
▸,b
▸; Zheng et al., 2006a
▸,b
▸; Zhu & Xiao, 2009 ▸). In spite of the fact that styphnates with protonated organic amine cations crystallize with difficulty (Vogel, 1978 ▸), they have received attention because of their high thermal stability (Abashev et al., 2001a
▸,b
▸; Deblitz et al., 2012 ▸; Kalaivani & Malarvizhi, 2010 ▸; Kalaivani et al., 2011 ▸; Kazheva et al., 2002 ▸; Liu et al., 2008 ▸; Refat et al., 2013 ▸; Tang et al., 2012 ▸; Zhang et al., 2012 ▸; Wu et al., 2013a
▸,b
▸,c
▸). Amorphous pyridinium styphnate has found applications in the preparation of chloropicryl chloride (Feuer & Harban, 1954 ▸). We report herein on the crystal structure of the title molecular salt.
Structural commentary
The molecular structure of the title molecular salt is depicted in Fig. 1 ▸. The asymmetric unit is comprised of one phenolate anion and a pyridinium cation. The loss of a single proton of the styphnate anion is confirmed by the increase in the bond lengths of the C—C bonds adjacent to the phenolate ion (C1—C2 and C2—C3), which are 1.439 (4) and 1.420 (4) Å, respectively. There is an increase of the value of the bond angles C2—C1—C6 and C2—C3—C4 in the benzene ring to 122.4 (3) and 126.3 (3)°, respectively, and a decrease of the C4—C5—C6 bond angle to 120.5 (2)° compared to the values observed for free styphic acid (Pierce-Butler, 1982 ▸). The nitro group (N3/O5/O6) flanked by the phenolate ion and the phenolic –OH group deviates noticeably from the benzene ring plane, subtending a dihedral angle of 89.2 (4)°. The other two nitro groups, O1/N1/O2 and O3/N2/O4, lie close to the plane of the attached benzene ring, making dihedral angles of 2.8 (4) and 3.4 (3) °, respectively. The nitro group (N2/O3/O4) para with respect to the phenolate O atom, O7, forms an intramolecular hydrogen bond with the adjacent phenolic –OH group (O8—H8), which results in an S(6) ring motif (Fig. 1 ▸ and Table 1 ▸).
Figure 1.
A view of the molecular structure of the title molecular salt, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines (see Table 1 ▸ for details).
Table 1. Hydrogen-bond geometry (, ).
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| N4H4AO1 | 0.90(2) | 2.22(4) | 2.946(4) | 137(4) |
| N4H4AO7 | 0.90(2) | 1.88(4) | 2.625(3) | 138(5) |
| O8H8AN2 | 0.82 | 2.48 | 2.905(3) | 113 |
| O8H8AO4 | 0.82 | 1.87 | 2.563(3) | 141 |
| O8H8AO6i | 0.82 | 2.63 | 3.110(4) | 119 |
| C8H8O6ii | 0.93 | 2.58 | 3.352(5) | 141 |
| C8H8O8iii | 0.93 | 2.63 | 3.405(4) | 141 |
| C10H10O2iv | 0.93 | 2.43 | 3.139(4) | 133 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
.
Supramolecular features
In the crystal, the cation and anion are linked via bifurcated N—H⋯(O,O) hydrogen bonds forming an (6) ring motif (Table 1 ▸ and Figs. 1 ▸ and 2 ▸). Inversion-related anions are connected through pairs of C—H⋯O hydrogen bonds, forming dimers enclosing an 
(10) ring motif. The phenolate oxygen, O7, is also bifurcated and forms hydrogen bonds with the protonated nitrogen atom, N4, of the pyridinium moiety and the C—H H atom adjacent to the protonated nitrogen atom, forming an 
(5) ring motif. The combination of these various N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds leads to the formation of a three-dimensional structure (Table 1 ▸ and Figs. 2 ▸ and 3 ▸).
Figure 2.
A view along the a axis of the crystal packing of the title molecular salt. Hydrogen bonds are shown as dashed lines (see Table 1 ▸ for details).
Figure 3.
A view along the b axis of the crystal packing of the title molecular salt. Hydrogen bonds are shown as dashed lines (see Table 1 ▸ for details).
Database survey
A search of the Cambridge Structural Database (Version 5.35, May 214; Groom & Allen, 2014 ▸) for 3-hydroxy-2,4,6-trinitrophenolates gave 14 hits. Six concern metal-complex cations, and the remaining eight concern organic cations. Amongst the latter are two compounds, referred to above in §1 for their high thermal stability, viz. 2-methoxyanilinium 3-hydroxy-2,4,6-trinitrophenolate (Kalaivani et al., 2011 ▸) and morpholinium 3-hydroxy-2,4,6-trinitrophenolate (Kalaivani & Malarvizhi, 2010 ▸).
Thermal behaviour and friction sensitivity
As styphnic acid derivatives are energetic salts, the thermal behaviour of the title molecular salt has also been examined. The exothermic decomposition has been observed at four different heating rates (5 K/min, 10 K/min, 20 K/min and 40 K/min). The title molecular salt decomposes (70–80%) in two stages. For each stage, the energy of activation was determined employing Kissinger (1957 ▸) [stage I: 27.2 kcal/mol; stage II: 50.5 kcal/mol] and Ozawa (1965 ▸) methods [stage I: 28.5 kcal/mol; stage II: 51.8 kcal/mol]. The title molecular salt was observed to be insensitive towards the impact of a 2 kg mass hammer up to the height limit (160 cm) of the instrument, even at the maximum energy level of 31.392 J (Meyer & Kohler, 1993a ▸). The friction sensitivity was determined under defined conditions according to the BAM method (Meyer & Kohler, 1993b ▸). The title molecular salt was insensitive at the maximum force of 360 Newton. The title molecular salt is an insensitive high-energy-density material, confirmed through the impact, friction-sensitivity test, and the energy of activation from TGA/DTA curves.
Synthesis and crystallization
Styphnic acid (2.45 g, 0.01 mol) dissolved in 25 mL of absolute alcohol was mixed with pyridine (0.79 g, 0.01 mol) and stirred continuously for 6 hrs and then kept aside for 2 h. The yellow-coloured amorphous solid obtained was filtered, washed with 30 ml of dry ether and recrystallized from ethylene glycol. Yellow crystals formed in an ethylene glycol solution after slow evaporation at 298 K over a period of 2 weeks (m.p: 455 K; yield: 80%).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The NH H atom was located from a difference Fourier map and freely refined. The OH and C-bound H atoms were included in calculated positions and treated as riding atoms: O—H = 0.82, C—H = 0.93 Å, with U iso(H) = 1.5U eq(O) for the hydroxyl H atom and = 1.2U eq(C) for the other H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C5H6N+C6H2N3O8 |
| M r | 324.21 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 296 |
| a, b, c () | 5.9506(2), 8.1608(3), 27.0175(10) |
| () | 90.379(5) |
| V (3) | 1311.99(8) |
| Z | 4 |
| Radiation type | Mo K |
| (mm1) | 0.14 |
| Crystal size (mm) | 0.35 0.35 0.30 |
| Data collection | |
| Diffractometer | Bruker Kappa APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2004 ▸) |
| T min, T max | 0.951, 0.959 |
| No. of measured, independent and observed [I > 2(I)] reflections | 14733, 2296, 1771 |
| R int | 0.047 |
| (sin /)max (1) | 0.595 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.059, 0.198, 1.14 |
| No. of reflections | 2296 |
| No. of parameters | 212 |
| No. of restraints | 1 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| max, min (e 3) | 0.32, 0.34 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027704/su5046sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027704/su5046Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014027704/su5046Isup3.cml
CCDC reference: 1006492
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are grateful to the UGC for financial support and the SAIF, IIT Madras, for the data collection.
supplementary crystallographic information
Crystal data
| C5H6N+·C6H2N3O8− | F(000) = 664 |
| Mr = 324.21 | Dx = 1.641 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 5354 reflections |
| a = 5.9506 (2) Å | θ = 2.6–26.1° |
| b = 8.1608 (3) Å | µ = 0.14 mm−1 |
| c = 27.0175 (10) Å | T = 296 K |
| β = 90.379 (5)° | Block, yellow |
| V = 1311.99 (8) Å3 | 0.35 × 0.35 × 0.30 mm |
| Z = 4 |
Data collection
| Bruker Kappa APEXII CCD diffractometer | 2296 independent reflections |
| Radiation source: fine-focus sealed tube | 1771 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.047 |
| ω and φ scan | θmax = 25.0°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −5→7 |
| Tmin = 0.951, Tmax = 0.959 | k = −9→9 |
| 14733 measured reflections | l = −32→32 |
Refinement
| 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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.198 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.14 | w = 1/[σ2(Fo2) + (0.1017P)2 + 0.9268P] where P = (Fo2 + 2Fc2)/3 |
| 2296 reflections | (Δ/σ)max < 0.001 |
| 212 parameters | Δρmax = 0.32 e Å−3 |
| 1 restraint | Δρmin = −0.34 e Å−3 |
Special details
| 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. |
| 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.5386 (5) | 0.1613 (3) | 0.08054 (10) | 0.0338 (6) | |
| C2 | 0.6344 (5) | 0.1587 (3) | 0.12957 (10) | 0.0335 (6) | |
| C3 | 0.5003 (5) | 0.0711 (3) | 0.16385 (10) | 0.0330 (6) | |
| C4 | 0.3031 (4) | −0.0084 (3) | 0.15364 (10) | 0.0331 (6) | |
| C5 | 0.2257 (4) | −0.0036 (3) | 0.10427 (10) | 0.0342 (7) | |
| C6 | 0.3424 (5) | 0.0820 (4) | 0.06890 (10) | 0.0372 (7) | |
| H6 | 0.2873 | 0.0862 | 0.0366 | 0.045* | |
| C7 | 1.2035 (5) | 0.4297 (4) | 0.17352 (12) | 0.0451 (8) | |
| H7 | 1.1200 | 0.3709 | 0.1964 | 0.054* | |
| C8 | 1.3941 (6) | 0.5094 (4) | 0.18837 (12) | 0.0485 (8) | |
| H8 | 1.4407 | 0.5063 | 0.2213 | 0.058* | |
| C9 | 1.5148 (6) | 0.5936 (4) | 0.15407 (12) | 0.0476 (8) | |
| H9 | 1.6461 | 0.6474 | 0.1635 | 0.057* | |
| C10 | 1.4438 (6) | 0.5993 (4) | 0.10590 (12) | 0.0488 (8) | |
| H10 | 1.5250 | 0.6577 | 0.0825 | 0.059* | |
| C11 | 1.2528 (6) | 0.5186 (4) | 0.09267 (12) | 0.0471 (8) | |
| H11 | 1.2027 | 0.5209 | 0.0600 | 0.057* | |
| N1 | 0.6481 (5) | 0.2501 (3) | 0.04118 (9) | 0.0477 (7) | |
| N2 | 0.0254 (4) | −0.0877 (3) | 0.09001 (10) | 0.0445 (7) | |
| N3 | 0.5834 (4) | 0.0636 (3) | 0.21455 (9) | 0.0436 (7) | |
| N4 | 1.1371 (4) | 0.4356 (3) | 0.12684 (10) | 0.0419 (6) | |
| O1 | 0.8179 (5) | 0.3281 (4) | 0.04960 (9) | 0.0730 (9) | |
| O2 | 0.5667 (5) | 0.2440 (5) | 0.00022 (10) | 0.0953 (12) | |
| O3 | −0.0431 (5) | −0.0774 (4) | 0.04783 (9) | 0.0732 (8) | |
| O4 | −0.0736 (4) | −0.1705 (3) | 0.12168 (9) | 0.0589 (7) | |
| O5 | 0.5195 (6) | 0.1641 (3) | 0.24370 (9) | 0.0800 (10) | |
| O6 | 0.7049 (5) | −0.0493 (5) | 0.22574 (10) | 0.0913 (11) | |
| O7 | 0.8146 (3) | 0.2234 (3) | 0.14326 (8) | 0.0493 (6) | |
| O8 | 0.1994 (4) | −0.0845 (3) | 0.19071 (8) | 0.0478 (6) | |
| H8A | 0.0816 | −0.1247 | 0.1805 | 0.072* | |
| H4A | 1.006 (6) | 0.388 (7) | 0.1186 (18) | 0.118 (19)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0332 (15) | 0.0309 (14) | 0.0374 (15) | −0.0026 (12) | 0.0065 (12) | −0.0001 (11) |
| C2 | 0.0283 (14) | 0.0298 (13) | 0.0424 (15) | 0.0001 (11) | 0.0028 (12) | −0.0035 (11) |
| C3 | 0.0324 (15) | 0.0339 (14) | 0.0327 (14) | −0.0014 (12) | −0.0003 (11) | −0.0011 (11) |
| C4 | 0.0317 (15) | 0.0281 (13) | 0.0397 (15) | −0.0009 (11) | 0.0066 (12) | −0.0007 (11) |
| C5 | 0.0261 (14) | 0.0323 (14) | 0.0441 (16) | −0.0023 (11) | −0.0006 (12) | −0.0039 (12) |
| C6 | 0.0367 (16) | 0.0374 (15) | 0.0374 (15) | 0.0010 (12) | −0.0014 (12) | −0.0043 (12) |
| C7 | 0.0468 (19) | 0.0385 (16) | 0.0503 (18) | −0.0043 (14) | 0.0104 (14) | 0.0022 (13) |
| C8 | 0.053 (2) | 0.0475 (18) | 0.0455 (17) | −0.0064 (16) | −0.0028 (15) | 0.0011 (14) |
| C9 | 0.0424 (18) | 0.0414 (17) | 0.059 (2) | −0.0093 (14) | −0.0024 (15) | −0.0018 (15) |
| C10 | 0.0491 (19) | 0.0419 (17) | 0.055 (2) | −0.0082 (15) | 0.0100 (15) | 0.0081 (14) |
| C11 | 0.053 (2) | 0.0450 (17) | 0.0432 (17) | −0.0018 (15) | −0.0018 (15) | 0.0019 (14) |
| N1 | 0.0497 (16) | 0.0525 (16) | 0.0408 (15) | −0.0080 (13) | 0.0037 (12) | 0.0065 (12) |
| N2 | 0.0343 (14) | 0.0446 (14) | 0.0544 (16) | −0.0056 (12) | 0.0010 (12) | −0.0080 (12) |
| N3 | 0.0395 (15) | 0.0515 (16) | 0.0398 (14) | −0.0069 (12) | 0.0005 (11) | 0.0036 (12) |
| N4 | 0.0349 (14) | 0.0362 (13) | 0.0547 (16) | −0.0041 (11) | 0.0008 (12) | −0.0050 (11) |
| O1 | 0.0702 (18) | 0.091 (2) | 0.0575 (15) | −0.0443 (16) | 0.0055 (13) | 0.0103 (14) |
| O2 | 0.092 (2) | 0.147 (3) | 0.0465 (15) | −0.054 (2) | −0.0129 (15) | 0.0350 (17) |
| O3 | 0.0594 (17) | 0.102 (2) | 0.0584 (16) | −0.0280 (15) | −0.0190 (13) | −0.0023 (15) |
| O4 | 0.0472 (14) | 0.0603 (15) | 0.0692 (16) | −0.0234 (12) | 0.0075 (12) | −0.0048 (12) |
| O5 | 0.133 (3) | 0.0616 (16) | 0.0453 (14) | 0.0037 (17) | −0.0071 (15) | −0.0118 (13) |
| O6 | 0.089 (2) | 0.124 (3) | 0.0600 (17) | 0.052 (2) | −0.0210 (15) | 0.0014 (17) |
| O7 | 0.0364 (12) | 0.0594 (14) | 0.0521 (13) | −0.0177 (10) | −0.0026 (10) | 0.0031 (10) |
| O8 | 0.0440 (13) | 0.0533 (13) | 0.0464 (12) | −0.0163 (10) | 0.0059 (10) | 0.0059 (10) |
Geometric parameters (Å, º)
| C1—C6 | 1.369 (4) | C8—H8 | 0.9300 |
| C1—C2 | 1.439 (4) | C9—C10 | 1.366 (4) |
| C1—N1 | 1.445 (4) | C9—H9 | 0.9300 |
| C2—O7 | 1.249 (3) | C10—C11 | 1.359 (5) |
| C2—C3 | 1.420 (4) | C10—H10 | 0.9300 |
| C3—C4 | 1.367 (4) | C11—N4 | 1.339 (4) |
| C3—N3 | 1.454 (4) | C11—H11 | 0.9300 |
| C4—O8 | 1.333 (3) | N1—O2 | 1.206 (4) |
| C4—C5 | 1.409 (4) | N1—O1 | 1.215 (4) |
| C5—C6 | 1.376 (4) | N2—O3 | 1.211 (3) |
| C5—N2 | 1.426 (4) | N2—O4 | 1.242 (3) |
| C6—H6 | 0.9300 | N3—O5 | 1.200 (4) |
| C7—N4 | 1.320 (4) | N3—O6 | 1.208 (4) |
| C7—C8 | 1.366 (5) | N4—H4A | 0.90 (2) |
| C7—H7 | 0.9300 | O8—H8A | 0.8200 |
| C8—C9 | 1.362 (5) | ||
| C6—C1—C2 | 122.4 (3) | C7—C8—H8 | 120.6 |
| C6—C1—N1 | 117.1 (3) | C8—C9—C10 | 120.3 (3) |
| C2—C1—N1 | 120.5 (2) | C8—C9—H9 | 119.9 |
| O7—C2—C3 | 120.3 (3) | C10—C9—H9 | 119.9 |
| O7—C2—C1 | 126.9 (3) | C11—C10—C9 | 119.1 (3) |
| C3—C2—C1 | 112.8 (2) | C11—C10—H10 | 120.4 |
| C4—C3—C2 | 126.3 (3) | C9—C10—H10 | 120.4 |
| C4—C3—N3 | 117.1 (2) | N4—C11—C10 | 119.8 (3) |
| C2—C3—N3 | 116.5 (2) | N4—C11—H11 | 120.1 |
| O8—C4—C3 | 118.1 (2) | C10—C11—H11 | 120.1 |
| O8—C4—C5 | 125.0 (2) | O2—N1—O1 | 121.5 (3) |
| C3—C4—C5 | 116.9 (2) | O2—N1—C1 | 118.3 (3) |
| C6—C5—C4 | 120.5 (2) | O1—N1—C1 | 120.2 (3) |
| C6—C5—N2 | 118.8 (3) | O3—N2—O4 | 121.9 (3) |
| C4—C5—N2 | 120.7 (3) | O3—N2—C5 | 119.8 (3) |
| C1—C6—C5 | 120.9 (3) | O4—N2—C5 | 118.4 (3) |
| C1—C6—H6 | 119.5 | O5—N3—O6 | 123.2 (3) |
| C5—C6—H6 | 119.5 | O5—N3—C3 | 118.8 (3) |
| N4—C7—C8 | 120.4 (3) | O6—N3—C3 | 117.8 (3) |
| N4—C7—H7 | 119.8 | C7—N4—C11 | 121.7 (3) |
| C8—C7—H7 | 119.8 | C7—N4—H4A | 118 (3) |
| C9—C8—C7 | 118.7 (3) | C11—N4—H4A | 120 (3) |
| C9—C8—H8 | 120.6 | C4—O8—H8A | 109.5 |
| C6—C1—C2—O7 | 178.0 (3) | N2—C5—C6—C1 | −178.3 (3) |
| N1—C1—C2—O7 | −2.3 (4) | N4—C7—C8—C9 | −0.6 (5) |
| C6—C1—C2—C3 | −2.0 (4) | C7—C8—C9—C10 | 0.8 (5) |
| N1—C1—C2—C3 | 177.7 (2) | C8—C9—C10—C11 | −0.7 (5) |
| O7—C2—C3—C4 | −178.4 (3) | C9—C10—C11—N4 | 0.3 (5) |
| C1—C2—C3—C4 | 1.6 (4) | C6—C1—N1—O2 | −3.0 (5) |
| O7—C2—C3—N3 | 0.6 (4) | C2—C1—N1—O2 | 177.3 (3) |
| C1—C2—C3—N3 | −179.4 (2) | C6—C1—N1—O1 | 177.1 (3) |
| C2—C3—C4—O8 | −179.9 (3) | C2—C1—N1—O1 | −2.6 (4) |
| N3—C3—C4—O8 | 1.1 (4) | C6—C5—N2—O3 | −2.8 (4) |
| C2—C3—C4—C5 | 0.3 (4) | C4—C5—N2—O3 | 177.3 (3) |
| N3—C3—C4—C5 | −178.7 (2) | C6—C5—N2—O4 | 177.0 (3) |
| O8—C4—C5—C6 | 178.3 (3) | C4—C5—N2—O4 | −2.9 (4) |
| C3—C4—C5—C6 | −1.9 (4) | C4—C3—N3—O5 | −87.2 (4) |
| O8—C4—C5—N2 | −1.8 (4) | C2—C3—N3—O5 | 93.7 (3) |
| C3—C4—C5—N2 | 178.0 (2) | C4—C3—N3—O6 | 89.1 (4) |
| C2—C1—C6—C5 | 0.6 (4) | C2—C3—N3—O6 | −90.0 (4) |
| N1—C1—C6—C5 | −179.2 (3) | C8—C7—N4—C11 | 0.2 (5) |
| C4—C5—C6—C1 | 1.5 (4) | C10—C11—N4—C7 | 0.0 (5) |
Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N4—H4A···O1 | 0.90 (2) | 2.22 (4) | 2.946 (4) | 137 (4) |
| N4—H4A···O7 | 0.90 (2) | 1.88 (4) | 2.625 (3) | 138 (5) |
| O8—H8A···N2 | 0.82 | 2.48 | 2.905 (3) | 113 |
| O8—H8A···O4 | 0.82 | 1.87 | 2.563 (3) | 141 |
| O8—H8A···O6i | 0.82 | 2.63 | 3.110 (4) | 119 |
| C8—H8···O6ii | 0.93 | 2.58 | 3.352 (5) | 141 |
| C8—H8···O8iii | 0.93 | 2.63 | 3.405 (4) | 141 |
| C10—H10···O2iv | 0.93 | 2.43 | 3.139 (4) | 133 |
Symmetry codes: (i) x−1, y, z; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+2, −y+1, −z.
References
- Abashev, G. G., Gritsenko, V. V., Kazheva, O. N., Tenishev, A. G., Canadell, E. & Dyachenk, O. A. (2001b). Z. Kristallogr. 216, 623–628.
- Abashev, G. G., Kazheva, O. N., Dyachenk, O. A., Gritsenko, V. V., Tenishev, A. G., Nishimura, K. & Saito, G. (2001a). Mendeleev Commun. 4, 125–127.
- Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350.
- Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
- Cui, Y., Zhang, T. L., Zhang, J. G. & Yang, L. (2008a). Chin. J. Chem. 26, 2021–2028.
- Cui, Y., Zhang, T. L., Zhang, J. G., Yang, L., Hu, X. C. & Zhang, J. (2008b). J. Mol. Struct. 889, 177–185.
- Deblitz, R., Hrib, C. G., Plenikowski, G. & Edelmann, F. T. (2012). Crystals, 2, 34–42.
- Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
- Feuer, H. & Harban, A. A. (1954). US Patent 2679538 A.
- Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. [DOI] [PubMed]
- Hu, R., Chen, S., Gao, S., Zhao, F., Luo, Y., Gao, H., Shi, Q., Zhao, H., Yao, P. & Li, J. (2005). J. Hazard. Mater. 117, 346–350. [DOI] [PubMed]
- Kalaivani, D. & Malarvizhi, R. (2010). Acta Cryst. E66, o2698. [DOI] [PMC free article] [PubMed]
- Kalaivani, D., Malarvizhi, R., Thanigaimani, K. & Muthiah, P. T. (2011). Acta Cryst. E67, o686. [DOI] [PMC free article] [PubMed]
- Kazheva, O. N., Canadell, E., Shilov, G. V., Abashev, G. G., Tenishev, A. G. & Dyachenk, O. A. (2002). Phys. E Low Dimens. Syst. Nanostruct. 13, 1268–1270.
- Kissinger, H. E. (1957). Anal. Chem. 29, 1702–1706.
- Liu, Z. H., Ao, G. J., Zhang, T. L., Yang, L., Zhang, J. G. & Zhang, Y. (2008). Wuji Huaxue Xuebao, 24, 1155–1159.
- Liu, J. W., Zhang, J. G., Zhang, T. L., Zheng, H., Yang, L. & Yu, K. B. (2009). Struct. Chem. 20, 387–392.
- Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.
- Meyer, R. & Kohler, J. (1993a). Editors. Explosives, 4th ed., revised and extended, p. 149. New York: VCH Publishers.
- Meyer, R. & Kohler, J. (1993b). Editors. Explosives, 4th ed., revised and extended, p. 197. New York: VCH Publishers.
- Orbovic, N. & Codoceo, C. L. (2008). Prop. Explos. Pyrotech. 33, 459–466.
- Ozawa, T. (1965). Bull. Chem. Soc. Jpn, 38, 1881–1886.
- Pierce-Butler, M. A. (1982). Acta Cryst. B38, 3097–3100.
- Refat, M. S., Saad, H. A., EI-Sayed, M. Y., Adam, A. M. A., Yeşilel, O. Z. & Taş, M. (2013). J. Chem. 2013, article ID 107515, 8 pages. 10.1155/2013/107515.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Tang, Z., Yang, L., Qiao, X. J., Wu, B. D., Zhang, T. L., Zhou, Z. N. & Yu, K. B. (2012). Chem. Res. Chin. Univ. 28, 4-8.
- Vogel, A. I. (1978). Textbook of Practical Organic Chemistry, 4th ed., p. 1093. London: Longman.
- Wu, J. T., Zhang, J. G., Sun, M., Yin, X. & Zhang, T. L. (2013b). New Trends Res. Energ. Mater. pp. 433–440.
- Wu, J. T., Zhang, J. G., Sun, M., Yin, X. & Zhang, T. L. (2013c). Cent. Eur. J. Energ. Mater. 10, 481–493.
- Wu, J. T., Zhang, J. G., Yin, X., Sun, M. & Zhang, T. L. (2013a). Z. Anorg. Allg. Chem. 639, 2354–2358.
- Zhang, J. G., Liang, Y. H., Feng, J. L., Wang, K., Zhang, T. L., Zhou, Z. N. & Yang, L. (2012). Z. Anorg. Allg. Chem. 638, 1212–1218.
- Zhang, J. G., Wang, K., Li, Z. M., Zheng, H., Zhang, T. L. & Yang, L. (2011a). Main Group Chem. 10, 205–213.
- Zhang, J., Wei, L., Cui, Y., Zhang, T., Zhou, Z. & Yong, L. (2011b). Z. Anorg. Allg. Chem. 637, 1527–1532.
- Zheng, H., Zhang, T. L., Zhang, J. G., Qiao, X. L., Yang, L. & Yu, K. B. (2006a). Wuji Huaxue Xuebao 22, 346–350.
- Zheng, H., Zhang, T. L., Zhang, J. G., Qiao, X. L., Yang, L. & Yu, K. B. (2006b). Chin. J. Chem. 24, 845–848.
- Zhu, W. & Xiao, H. (2009). J. Phys. Chem. B, 113, 10315–10321. [DOI] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027704/su5046sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027704/su5046Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989014027704/su5046Isup3.cml
CCDC reference: 1006492
Additional supporting information: crystallographic information; 3D view; checkCIF report