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organic compounds
10-Formyl-2,4,6,8,12-pentanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,9.03,11]dodecane acetone solvate
aSchool of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, People's Republic of China, and bGansu Yinguang Chemical Industry Group Co. Ltd, Gansu 730900, People's Republic of China
*Correspondence e-mail: nanfei314@126.com
The title compound, C7H7N11O11·C3H6O, consisting of one molecule of 10-formyl-2,4,6,8,12-pentanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,9.03,11]dodecane (pentanitromonoformylhexaazaisowurtzitane, PNMFIW) and one acetone solvent molecule, is a member of the caged hexaazaisowurtzitane family. PNMFIW has a cage structure which is constructed from one six-membered and two five-membered rings which are linked by a C—C bond, thus creating two seven-membered rings. In the PNMFIW molecule, one formyl group is bonded to the N heteroatom of the six-membered cycle, and five nitro groups are appended to other five N heteroatom of the caged structure. The acetone solvent molecule is arranged beside a five-membered plane of PNMFIW with an O atom and an H atom close (with respect to the sum of the van der Waals radii) to the neighbouring nitro O atom [O⋯O = 2.957 (3) and 2.852 (3) Å; O⋯ H = 2.692 (2), 2.526 (3) and 2.432 (3) Å].
Related literature
For the synthesis see: Golfier et al. (1998); Liu et al. (2006
); Ou et al. (2000
). For structures with similar properties, see: Chen et al. (2010
); Jin et al. (2009
); Lu et al. (2004
).
Experimental
Crystal data
|
Data collection: CrystalClear (Rigaku, 2008); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: CrystalClear; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536810002813/bg2324sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002813/bg2324Isup2.hkl
Fuming sulfuric acid was slowly added into fuming nitric acid in a three-neck flask with stirring. After the solution of mixed acids was heated to 60 0C, tetraacetyldiformylhexaazaisowurtzitane (10 g) was added, and then the temperature was elevated to 65 0C. The solution was maintained at 65 0C for 12 h; thereafter the solution was poured into ice-water. The precipitated solid was filtered off, washed with water and then dried. The obtained solid was a mixture of polynitrohexaazaisowurtzitane derivatives with different number of nitro substitutes. Pure PNMFIW was obtained through a silica
with hexane/acetyl acetate (6/4 by volume) as mobile phase at room temperature (25 0C).Pure PNMFIW was dissolved in solvent of acetone, and then the resulted solution was placed in ambient condition (288–293 K). About a week later, single crystals was obtained by controlling the evaporation of solvent. The
of PNMFIW solvate was determined by single-crystal X-ray diffraction.All non-hydrogen atoms were obtained using the
The hydrogen atom were placed geometrically and treated by a The distances of methane and methene are 1.000 A, and the distance of carbonyl is 0.950 A. The Ueq of H is assigned 1.2 time Ueq of C linked.Title compound is a solvate of PNMFIW (I) with acetone. PNMFIW was even known as a by-product in the synthesis of hexanitrohexaazawurtzitane (HNIW) (Golfier et al., 1998; Liu et al.,2006). We determined the single structures of PNMFIW (Jin et al., 2009) and the analog of TNDFIW (Chen et al., 2010) not long ago, further the titled solvate of PNMFIW was obtained by crystallization in acetone solvent.
Figure 1 shows the molecular structure of PNMFIW solvate with acetone. The caged structure of compound (I) is constructed from one six-membered and two five-membered rings which are closed by the C1—C4 bond, thus creating two seven-membered rings. The six-membered pyrazine ring in compound (I) is shaped like a boat, while more stable conformation of six-membered ringis chair form. The two five-membered rings are also non-planar, being characterized by the torsion angles of two five-membered rings. Four nitro groups are appended to the four nitrogen atoms of the two five-membered rings, while a nitro group and a formyl are attached to the two nitrogen atoms of the six-membered ring respectively. It was observed that the acetone molecule is arranged beside a five-membered plane of compound (I) molecule and the skeleton of acetone molecule is nearly perpendicular to the five-membered plane with oxygen atom and a hydrogen atom of acetone significantly closed to the neighbouring nitro oxygen atom of compound (I). The inter molecular distance of O12 of acetone to C2, C3, O2 and O4 are 2.9378 (5), 2.9811 (3), 2.8523 (4) and 2.9567 angstrom much less than the sum of the van der Waals radii respectively,the closed intermolecular contact different from those of the common organic complex (Lu et al., 2004) results the high denstity of 1.723 g/cm3.
For the synthesis see: Golfier et al. (1998); Liu et al. (2006); Ou et al. (2000). For structures with similar properties, see: Chen et al. (2010); Jin et al. (2009); Lu et al. (2004).
Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: CrystalClear (Rigaku, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008). ![]() | Fig. 1. Molecular structure of PNMFIW-acetone with labelling and displacement ellipsoids drawn at the 30% probability level. |
C7H7N11O11·C3H6O | F(000) = 492 |
Mr = 479.31 | Dx = 1.723 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3051 reflections |
a = 10.432 (3) Å | θ = 3.2–27.5° |
b = 7.9230 (19) Å | µ = 0.16 mm−1 |
c = 12.191 (3) Å | T = 93 K |
β = 113.493 (2)° | Prism, colorless |
V = 924.1 (4) Å3 | 0.60 × 0.27 × 0.17 mm |
Z = 2 |
Rigaku Saturn724+ diffractometer | 2056 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.033 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
Detector resolution: 28.5714 pixels mm-1 | h = −12→13 |
multi–scan | k = −10→10 |
7388 measured reflections | l = −15→13 |
2257 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0252P)2 + 0.266P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
2257 reflections | Δρmax = 0.37 e Å−3 |
301 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0080 (18) |
C7H7N11O11·C3H6O | V = 924.1 (4) Å3 |
Mr = 479.31 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.432 (3) Å | µ = 0.16 mm−1 |
b = 7.9230 (19) Å | T = 93 K |
c = 12.191 (3) Å | 0.60 × 0.27 × 0.17 mm |
β = 113.493 (2)° |
Rigaku Saturn724+ diffractometer | 2056 reflections with I > 2σ(I) |
7388 measured reflections | Rint = 0.033 |
2257 independent reflections |
R[F2 > 2σ(F2)] = 0.035 | 1 restraint |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.37 e Å−3 |
2257 reflections | Δρmin = −0.25 e Å−3 |
301 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. Since the absolute configuration for the compound could not reliably be determined from Mo Kα data, the Friedel equivalents were merged before the final cycles of 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 | 0.5840 (2) | 0.7433 (3) | 0.04548 (16) | 0.0252 (5) | |
O2 | 0.6865 (2) | 0.8921 (2) | 0.20784 (17) | 0.0208 (4) | |
O3 | 0.7530 (2) | 0.3757 (3) | 0.03918 (17) | 0.0271 (5) | |
O4 | 0.9429 (2) | 0.3367 (3) | 0.19951 (17) | 0.0250 (5) | |
O5 | 0.2870 (2) | 0.5826 (3) | 0.15535 (18) | 0.0406 (7) | |
O6 | 0.3470 (2) | 0.6539 (3) | 0.34336 (18) | 0.0331 (6) | |
O7 | 0.39153 (19) | 0.0497 (3) | 0.18497 (17) | 0.0250 (5) | |
O8 | 0.54005 (18) | −0.0268 (2) | 0.36166 (16) | 0.0192 (4) | |
O9 | 0.64166 (18) | 0.7130 (3) | 0.58913 (16) | 0.0189 (4) | |
O10 | 0.99291 (18) | 0.1958 (3) | 0.44466 (16) | 0.0211 (4) | |
O11 | 0.85172 (19) | 0.0667 (3) | 0.50810 (17) | 0.0256 (5) | |
O12 | 0.9308 (2) | 0.7045 (3) | 0.23532 (19) | 0.0271 (5) | |
N1 | 0.6275 (2) | 0.6249 (3) | 0.22275 (18) | 0.0140 (5) | |
N2 | 0.7407 (2) | 0.3766 (3) | 0.21929 (18) | 0.0136 (5) | |
N3 | 0.4655 (2) | 0.4602 (3) | 0.29591 (18) | 0.0146 (5) | |
N4 | 0.5722 (2) | 0.2200 (3) | 0.28704 (18) | 0.0134 (5) | |
N5 | 0.6735 (2) | 0.5978 (3) | 0.43095 (17) | 0.0120 (4) | |
N6 | 0.7940 (2) | 0.3236 (3) | 0.42695 (18) | 0.0135 (5) | |
N7 | 0.6364 (2) | 0.7627 (3) | 0.1538 (2) | 0.0180 (5) | |
N8 | 0.8190 (2) | 0.3654 (3) | 0.1471 (2) | 0.0188 (5) | |
N9 | 0.3605 (2) | 0.5725 (3) | 0.2628 (2) | 0.0232 (5) | |
N10 | 0.4930 (2) | 0.0712 (3) | 0.27833 (19) | 0.0158 (5) | |
N11 | 0.8852 (2) | 0.1841 (3) | 0.46067 (19) | 0.0171 (5) | |
C1 | 0.6046 (3) | 0.4582 (3) | 0.1680 (2) | 0.0152 (5) | |
H1 | 0.5683 | 0.4648 | 0.0788 | 0.018* | |
C2 | 0.7369 (3) | 0.6089 (3) | 0.3454 (2) | 0.0123 (5) | |
H2 | 0.8035 | 0.7059 | 0.3646 | 0.015* | |
C3 | 0.8126 (3) | 0.4392 (3) | 0.3415 (2) | 0.0146 (5) | |
H3 | 0.9141 | 0.4587 | 0.3609 | 0.018* | |
C4 | 0.4998 (3) | 0.3609 (3) | 0.2111 (2) | 0.0155 (6) | |
H4 | 0.4139 | 0.3231 | 0.1420 | 0.019* | |
C5 | 0.5788 (2) | 0.4581 (3) | 0.4144 (2) | 0.0129 (5) | |
H5 | 0.5417 | 0.4560 | 0.4784 | 0.015* | |
C6 | 0.6499 (3) | 0.2865 (3) | 0.4086 (2) | 0.0145 (6) | |
H6 | 0.6463 | 0.2060 | 0.4705 | 0.017* | |
C7 | 0.6967 (3) | 0.7161 (3) | 0.5185 (2) | 0.0147 (5) | |
H7 | 0.7595 | 0.8058 | 0.5242 | 0.018* | |
C8 | 0.9431 (3) | 0.7608 (5) | 0.0488 (3) | 0.0360 (8) | |
H8A | 0.8787 | 0.6650 | 0.0214 | 0.043* | |
H8B | 1.0279 | 0.7365 | 0.0355 | 0.043* | |
H8C | 0.8980 | 0.8622 | 0.0040 | 0.043* | |
C9 | 0.9808 (3) | 0.7892 (4) | 0.1793 (3) | 0.0217 (6) | |
C10 | 1.0817 (3) | 0.9294 (4) | 0.2373 (3) | 0.0312 (7) | |
H10A | 1.0981 | 0.9365 | 0.3221 | 0.037* | |
H10B | 1.0427 | 1.0364 | 0.1977 | 0.037* | |
H10C | 1.1703 | 0.9071 | 0.2299 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0340 (12) | 0.0276 (12) | 0.0130 (9) | 0.0047 (10) | 0.0083 (8) | 0.0063 (9) |
O2 | 0.0290 (11) | 0.0116 (10) | 0.0263 (10) | 0.0013 (8) | 0.0157 (9) | 0.0005 (9) |
O3 | 0.0319 (11) | 0.0378 (13) | 0.0151 (9) | 0.0058 (11) | 0.0130 (8) | 0.0002 (10) |
O4 | 0.0212 (10) | 0.0296 (13) | 0.0283 (11) | 0.0079 (10) | 0.0144 (9) | 0.0010 (9) |
O5 | 0.0390 (13) | 0.0483 (17) | 0.0197 (11) | 0.0220 (13) | −0.0038 (9) | −0.0022 (11) |
O6 | 0.0302 (12) | 0.0425 (15) | 0.0235 (11) | 0.0185 (10) | 0.0075 (9) | −0.0069 (11) |
O7 | 0.0249 (10) | 0.0262 (12) | 0.0188 (10) | −0.0115 (9) | 0.0035 (8) | −0.0052 (9) |
O8 | 0.0236 (10) | 0.0142 (11) | 0.0215 (10) | 0.0010 (8) | 0.0109 (8) | 0.0034 (8) |
O9 | 0.0222 (10) | 0.0207 (10) | 0.0183 (9) | −0.0016 (9) | 0.0127 (8) | −0.0022 (8) |
O10 | 0.0135 (9) | 0.0226 (11) | 0.0288 (11) | 0.0033 (9) | 0.0101 (8) | 0.0046 (9) |
O11 | 0.0216 (10) | 0.0167 (11) | 0.0359 (12) | 0.0008 (9) | 0.0088 (9) | 0.0115 (10) |
O12 | 0.0294 (11) | 0.0256 (12) | 0.0345 (12) | 0.0029 (10) | 0.0215 (9) | 0.0088 (10) |
N1 | 0.0181 (11) | 0.0126 (11) | 0.0108 (10) | 0.0006 (9) | 0.0054 (8) | 0.0037 (9) |
N2 | 0.0145 (10) | 0.0162 (11) | 0.0122 (10) | 0.0003 (9) | 0.0075 (8) | −0.0009 (9) |
N3 | 0.0126 (10) | 0.0175 (12) | 0.0123 (10) | 0.0033 (9) | 0.0033 (8) | −0.0003 (9) |
N4 | 0.0157 (10) | 0.0096 (11) | 0.0140 (11) | −0.0030 (9) | 0.0051 (8) | −0.0008 (9) |
N5 | 0.0146 (10) | 0.0119 (11) | 0.0113 (10) | −0.0007 (9) | 0.0070 (8) | −0.0008 (9) |
N6 | 0.0119 (10) | 0.0116 (11) | 0.0157 (11) | 0.0042 (9) | 0.0040 (8) | 0.0035 (9) |
N7 | 0.0212 (12) | 0.0178 (13) | 0.0188 (12) | 0.0064 (10) | 0.0120 (10) | 0.0069 (11) |
N8 | 0.0223 (12) | 0.0176 (12) | 0.0199 (12) | 0.0035 (11) | 0.0122 (10) | −0.0006 (10) |
N9 | 0.0208 (12) | 0.0254 (14) | 0.0190 (12) | 0.0099 (11) | 0.0033 (10) | 0.0003 (11) |
N10 | 0.0172 (11) | 0.0150 (12) | 0.0182 (11) | −0.0030 (10) | 0.0103 (9) | −0.0032 (10) |
N11 | 0.0155 (11) | 0.0144 (12) | 0.0181 (11) | 0.0030 (10) | 0.0032 (9) | 0.0006 (10) |
C1 | 0.0174 (13) | 0.0147 (14) | 0.0143 (12) | 0.0014 (12) | 0.0071 (10) | −0.0008 (11) |
C2 | 0.0130 (12) | 0.0128 (14) | 0.0119 (12) | 0.0010 (11) | 0.0059 (10) | 0.0010 (10) |
C3 | 0.0154 (12) | 0.0159 (14) | 0.0122 (12) | −0.0018 (11) | 0.0049 (10) | 0.0010 (11) |
C4 | 0.0172 (13) | 0.0137 (14) | 0.0148 (12) | 0.0019 (11) | 0.0056 (10) | 0.0012 (11) |
C5 | 0.0149 (12) | 0.0128 (13) | 0.0104 (12) | 0.0002 (11) | 0.0045 (10) | −0.0003 (10) |
C6 | 0.0139 (12) | 0.0155 (14) | 0.0120 (12) | −0.0017 (11) | 0.0029 (10) | 0.0016 (10) |
C7 | 0.0146 (12) | 0.0105 (13) | 0.0173 (13) | 0.0030 (11) | 0.0044 (10) | −0.0020 (11) |
C8 | 0.0340 (18) | 0.044 (2) | 0.0315 (17) | −0.0045 (17) | 0.0144 (14) | 0.0075 (16) |
C9 | 0.0178 (14) | 0.0197 (16) | 0.0316 (16) | 0.0056 (12) | 0.0141 (12) | 0.0072 (13) |
C10 | 0.0318 (16) | 0.0246 (17) | 0.0395 (18) | 0.0004 (15) | 0.0165 (14) | 0.0046 (15) |
O1—N7 | 1.221 (3) | N5—C7 | 1.368 (3) |
O2—N7 | 1.218 (3) | N5—C5 | 1.443 (3) |
O3—N8 | 1.220 (3) | N5—C2 | 1.443 (3) |
O4—N8 | 1.213 (3) | N6—N11 | 1.409 (3) |
O5—N9 | 1.229 (3) | N6—C3 | 1.458 (3) |
O6—N9 | 1.229 (3) | N6—C6 | 1.458 (3) |
O7—N10 | 1.219 (3) | C1—C4 | 1.589 (4) |
O8—N10 | 1.216 (3) | C1—H1 | 1.0000 |
O9—C7 | 1.211 (3) | C2—C3 | 1.570 (4) |
O10—N11 | 1.218 (3) | C2—H2 | 1.0000 |
O11—N11 | 1.218 (3) | C3—H3 | 1.0000 |
O12—C9 | 1.213 (3) | C4—H4 | 1.0000 |
N1—N7 | 1.403 (3) | C5—C6 | 1.564 (4) |
N1—C1 | 1.456 (3) | C5—H5 | 1.0000 |
N1—C2 | 1.481 (3) | C6—H6 | 1.0000 |
N2—N8 | 1.423 (3) | C7—H7 | 0.9500 |
N2—C1 | 1.455 (3) | C8—C9 | 1.496 (4) |
N2—C3 | 1.462 (3) | C8—H8A | 0.9800 |
N3—N9 | 1.342 (3) | C8—H8B | 0.9800 |
N3—C4 | 1.453 (3) | C8—H8C | 0.9800 |
N3—C5 | 1.457 (3) | C9—C10 | 1.499 (4) |
N4—N10 | 1.419 (3) | C10—H10A | 0.9800 |
N4—C4 | 1.455 (3) | C10—H10B | 0.9800 |
N4—C6 | 1.474 (3) | C10—H10C | 0.9800 |
N7—N1—C1 | 117.98 (19) | C3—C2—H2 | 110.7 |
N7—N1—C2 | 117.6 (2) | N6—C3—N2 | 110.8 (2) |
C1—N1—C2 | 107.7 (2) | N6—C3—C2 | 107.71 (19) |
N8—N2—C1 | 117.7 (2) | N2—C3—C2 | 105.15 (19) |
N8—N2—C3 | 117.61 (19) | N6—C3—H3 | 111.0 |
C1—N2—C3 | 107.70 (19) | N2—C3—H3 | 111.0 |
N9—N3—C4 | 123.2 (2) | C2—C3—H3 | 111.0 |
N9—N3—C5 | 123.3 (2) | N3—C4—N4 | 100.13 (19) |
C4—N3—C5 | 111.5 (2) | N3—C4—C1 | 111.7 (2) |
N10—N4—C4 | 116.78 (19) | N4—C4—C1 | 109.3 (2) |
N10—N4—C6 | 116.27 (19) | N3—C4—H4 | 111.7 |
C4—N4—C6 | 107.7 (2) | N4—C4—H4 | 111.7 |
C7—N5—C5 | 122.2 (2) | C1—C4—H4 | 111.7 |
C7—N5—C2 | 122.2 (2) | N5—C5—N3 | 111.7 (2) |
C5—N5—C2 | 115.5 (2) | N5—C5—C6 | 111.27 (18) |
N11—N6—C3 | 115.72 (19) | N3—C5—C6 | 100.23 (19) |
N11—N6—C6 | 115.0 (2) | N5—C5—H5 | 111.1 |
C3—N6—C6 | 116.11 (19) | N3—C5—H5 | 111.1 |
O2—N7—O1 | 126.9 (2) | C6—C5—H5 | 111.1 |
O2—N7—N1 | 116.6 (2) | N6—C6—N4 | 110.3 (2) |
O1—N7—N1 | 116.2 (2) | N6—C6—C5 | 107.2 (2) |
O4—N8—O3 | 127.3 (2) | N4—C6—C5 | 106.0 (2) |
O4—N8—N2 | 116.1 (2) | N6—C6—H6 | 111.1 |
O3—N8—N2 | 116.5 (2) | N4—C6—H6 | 111.1 |
O6—N9—O5 | 126.6 (2) | C5—C6—H6 | 111.1 |
O6—N9—N3 | 116.6 (2) | O9—C7—N5 | 123.7 (2) |
O5—N9—N3 | 116.8 (2) | O9—C7—H7 | 118.2 |
O8—N10—O7 | 127.0 (2) | N5—C7—H7 | 118.2 |
O8—N10—N4 | 116.1 (2) | C9—C8—H8A | 109.5 |
O7—N10—N4 | 116.7 (2) | C9—C8—H8B | 109.5 |
O10—N11—O11 | 126.3 (2) | H8A—C8—H8B | 109.5 |
O10—N11—N6 | 116.9 (2) | C9—C8—H8C | 109.5 |
O11—N11—N6 | 116.7 (2) | H8A—C8—H8C | 109.5 |
N2—C1—N1 | 104.6 (2) | H8B—C8—H8C | 109.5 |
N2—C1—C4 | 109.0 (2) | O12—C9—C8 | 121.7 (3) |
N1—C1—C4 | 107.3 (2) | O12—C9—C10 | 121.5 (3) |
N2—C1—H1 | 111.9 | C8—C9—C10 | 116.8 (3) |
N1—C1—H1 | 111.9 | C9—C10—H10A | 109.5 |
C4—C1—H1 | 111.9 | C9—C10—H10B | 109.5 |
N5—C2—N1 | 110.14 (19) | H10A—C10—H10B | 109.5 |
N5—C2—C3 | 110.5 (2) | C9—C10—H10C | 109.5 |
N1—C2—C3 | 103.72 (19) | H10A—C10—H10C | 109.5 |
N5—C2—H2 | 110.7 | H10B—C10—H10C | 109.5 |
N1—C2—H2 | 110.7 | ||
C1—N1—N7—O2 | −163.7 (2) | C1—N2—C3—N6 | 96.0 (2) |
C2—N1—N7—O2 | −31.9 (3) | N8—N2—C3—C2 | 115.7 (2) |
C1—N1—N7—O1 | 21.3 (3) | C1—N2—C3—C2 | −20.1 (2) |
C2—N1—N7—O1 | 153.1 (2) | N5—C2—C3—N6 | 0.0 (3) |
C1—N2—N8—O4 | 162.3 (2) | N1—C2—C3—N6 | −118.0 (2) |
C3—N2—N8—O4 | 30.8 (3) | N5—C2—C3—N2 | 118.2 (2) |
C1—N2—N8—O3 | −22.0 (3) | N1—C2—C3—N2 | 0.2 (2) |
C3—N2—N8—O3 | −153.4 (2) | N9—N3—C4—N4 | −157.0 (2) |
C4—N3—N9—O6 | −176.6 (2) | C5—N3—C4—N4 | 38.7 (3) |
C5—N3—N9—O6 | −14.2 (4) | N9—N3—C4—C1 | 87.3 (3) |
C4—N3—N9—O5 | 3.9 (4) | C5—N3—C4—C1 | −76.9 (3) |
C5—N3—N9—O5 | 166.3 (3) | N10—N4—C4—N3 | 98.0 (2) |
C4—N4—N10—O8 | −160.9 (2) | C6—N4—C4—N3 | −34.9 (2) |
C6—N4—N10—O8 | −32.0 (3) | N10—N4—C4—C1 | −144.5 (2) |
C4—N4—N10—O7 | 24.3 (3) | C6—N4—C4—C1 | 82.6 (2) |
C6—N4—N10—O7 | 153.2 (2) | N2—C1—C4—N3 | 109.2 (2) |
C3—N6—N11—O10 | 20.2 (3) | N1—C1—C4—N3 | −3.5 (3) |
C6—N6—N11—O10 | 160.0 (2) | N2—C1—C4—N4 | −0.7 (3) |
C3—N6—N11—O11 | −163.0 (2) | N1—C1—C4—N4 | −113.4 (2) |
C6—N6—N11—O11 | −23.3 (3) | C7—N5—C5—N3 | 119.7 (2) |
N8—N2—C1—N1 | −103.0 (2) | C2—N5—C5—N3 | −57.4 (3) |
C3—N2—C1—N1 | 32.7 (2) | C7—N5—C5—C6 | −129.2 (2) |
N8—N2—C1—C4 | 142.5 (2) | C2—N5—C5—C6 | 53.7 (3) |
C3—N2—C1—C4 | −81.7 (2) | N9—N3—C5—N5 | −72.2 (3) |
N7—N1—C1—N2 | 103.4 (2) | C4—N3—C5—N5 | 92.0 (2) |
C2—N1—C1—N2 | −32.6 (2) | N9—N3—C5—C6 | 169.9 (2) |
N7—N1—C1—C4 | −140.9 (2) | C4—N3—C5—C6 | −25.9 (3) |
C2—N1—C1—C4 | 83.0 (2) | N11—N6—C6—N4 | −83.5 (2) |
C7—N5—C2—N1 | −117.8 (2) | C3—N6—C6—N4 | 56.1 (3) |
C5—N5—C2—N1 | 59.3 (3) | N11—N6—C6—C5 | 161.54 (19) |
C7—N5—C2—C3 | 128.1 (2) | C3—N6—C6—C5 | −58.9 (3) |
C5—N5—C2—C3 | −54.7 (3) | N10—N4—C6—N6 | 131.7 (2) |
N7—N1—C2—N5 | 125.2 (2) | C4—N4—C6—N6 | −95.1 (2) |
C1—N1—C2—N5 | −98.5 (2) | N10—N4—C6—C5 | −112.6 (2) |
N7—N1—C2—C3 | −116.5 (2) | C4—N4—C6—C5 | 20.6 (3) |
C1—N1—C2—C3 | 19.8 (2) | N5—C5—C6—N6 | 2.2 (3) |
N11—N6—C3—N2 | 82.5 (2) | N3—C5—C6—N6 | 120.5 (2) |
C6—N6—C3—N2 | −56.8 (3) | N5—C5—C6—N4 | −115.5 (2) |
N11—N6—C3—C2 | −163.00 (19) | N3—C5—C6—N4 | 2.7 (2) |
C6—N6—C3—C2 | 57.7 (3) | C5—N5—C7—O9 | 0.7 (4) |
N8—N2—C3—N6 | −128.2 (2) | C2—N5—C7—O9 | 177.6 (2) |
Experimental details
Crystal data | |
Chemical formula | C7H7N11O11·C3H6O |
Mr | 479.31 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 93 |
a, b, c (Å) | 10.432 (3), 7.9230 (19), 12.191 (3) |
β (°) | 113.493 (2) |
V (Å3) | 924.1 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.60 × 0.27 × 0.17 |
Data collection | |
Diffractometer | Rigaku Saturn724+ |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7388, 2257, 2056 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.066, 1.00 |
No. of reflections | 2257 |
No. of parameters | 301 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.25 |
Computer programs: CrystalClear (Rigaku, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
References
Chen, H., Shi, R., Chen, S., Jin, S., Li, L. & Shi, Y. (2010). Acta Cryst. E66, o338. Web of Science CSD CrossRef IUCr Journals Google Scholar
Golfier, M., Graindorge, H., Longevialle, Y. & Mace, H. (1998). Proceedings of the 29th International Annual Conference of ICT, Karlsruhe, March 1–17. Google Scholar
Jin, S., Chen, S., Chen, H., Li, L. & Shi, Y. (2009). Acta Cryst. E65, o3112. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, J., Jin, S. & Shu, Q. (2006). Chin. J. Ener. Mat. 14, 346–349. CAS Google Scholar
Lu, L.-P., Qin, S.-D., Zhu, M.-L. & Yang, P. (2004). Acta Cryst. E60, o583–o585. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ou, Y., Xu, Y., Chen, B., Liu, L. & Wang, C. (2000). Chin. J. Org. Chem. 20, 556–559 CAS Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Title compound is a solvate of PNMFIW (I) with acetone. PNMFIW was even known as a by-product in the synthesis of hexanitrohexaazawurtzitane (HNIW) (Golfier et al., 1998; Liu et al.,2006). We determined the single structures of PNMFIW (Jin et al., 2009) and the analog of TNDFIW (Chen et al., 2010) not long ago, further the titled solvate of PNMFIW was obtained by crystallization in acetone solvent.
Figure 1 shows the molecular structure of PNMFIW solvate with acetone. The caged structure of compound (I) is constructed from one six-membered and two five-membered rings which are closed by the C1—C4 bond, thus creating two seven-membered rings. The six-membered pyrazine ring in compound (I) is shaped like a boat, while more stable conformation of six-membered ringis chair form. The two five-membered rings are also non-planar, being characterized by the torsion angles of two five-membered rings. Four nitro groups are appended to the four nitrogen atoms of the two five-membered rings, while a nitro group and a formyl are attached to the two nitrogen atoms of the six-membered ring respectively. It was observed that the acetone molecule is arranged beside a five-membered plane of compound (I) molecule and the skeleton of acetone molecule is nearly perpendicular to the five-membered plane with oxygen atom and a hydrogen atom of acetone significantly closed to the neighbouring nitro oxygen atom of compound (I). The inter molecular distance of O12 of acetone to C2, C3, O2 and O4 are 2.9378 (5), 2.9811 (3), 2.8523 (4) and 2.9567 angstrom much less than the sum of the van der Waals radii respectively,the closed intermolecular contact different from those of the common organic complex (Lu et al., 2004) results the high denstity of 1.723 g/cm3.