4,10-Diformyl-2,6,8,12-tetra­nitro-2,4,6,8,10,12-hexa­azatetra­cyclo­[5.5.0.05,9.03,11]dodeca­ne

Chen, H.; Shi, R.; Chen, S.; Jin, S.; Li, L.; Shi, Y.

doi:10.1107/S1600536809055676

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o338

https://doi.org/10.1107/S1600536809055676

Open

access

4,10-Diformyl-2,6,8,12-tetranitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0^5,9.0^3,11]dodecane

Huaxiong Chen,^a Rui Shi,^a Shusen Chen,^a Shaohua Jin,^a ^* Lijie Li ^a and Yanshan Shi ^a

^aSchool of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: nanfei314@126.com

(Received 21 October 2009; accepted 29 December 2009; online 13 January 2010)

The title compound TNDFIW, C₈H₈N₁₀O₁₀, is a caged heterocycle substituted with four nitro and two formyl groups. It is related to the hexaazaisowurtzitane family of high-density high-energy polycyclic cage compounds. Four nitro groups are appended to the four N atoms of the two five-membered rings, while the other two formyl groups are attached to the two N atoms of the six-membered ring, which adopts a boat conformation. The compound has a cage structure which is constructed from one six-membered and two five-membered rings which are closed by a C—C bond, thus creating two seven-membered rings. There are a number of close intermolecular contacts [O⋯O = 2.827 (5), 2.853 (4) and 2.891 (5) Å; O⋯N = 2.746 (2) and 2.895 (2) Å] The calculated density of TNDFIW is 1.891 Mg m⁻³.

Related literature

For the synthesis, structure and properties of a related compound, see: Keshavarz et al. (2009 ); Liu et al. (2006 ); Ou et al. (2000 ); Jin et al. (2009 ). For sp³ bond angles, see: Zarychta et al. (2005 ).

Experimental

Crystal data

C₈H₈N₁₀O₁₀
M_r = 404.24
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.7794 (15) Å
b = 12.715 (2) Å
c = 12.716 (2) Å
V = 1419.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 93 K
0.20 × 0.13 × 0.09 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
11584 measured reflections
1866 independent reflections
1786 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.094
S = 1.00
1866 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809055676/fl2282sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055676/fl2282Isup2.hkl

checkCIF report

Comment top

The title compound, TNDFIW, is an incompletely nitrated product of tetraacyl-diformyl-hexaazaisowurtzitane (TADFIW). Another incompletely-nitrated product of TADFIW, pentanitro-monoformyl-hexaazaisowurtzitane (PNMFIW), is a by-product formed in the synthesis of hexanitro-hexaazaisowurtzitane (HNIW) (Ou et al., 2000; Liu et al., 2006). The single-crystal structure of PNMFIW has been reported recently (Jin et al., 2009). Slight variations of the structure of PNMFIW may result in a large decrease of sensitivity but with little loss of energy density according to the initiation mechanism (Keshavarz, et al., 2009). Therefore, the HNIW derivatives substituted by fewer nitro groups such as PNMFIW and TNDFIW may have much lower sensitivity than HNIW but have similar energy.

The caged structure of HNIW 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 has a boat conformation, while the more stable conformation of a six-membered ring is the chair form. Four nitro groups are appended to the four nitrogen atoms of the two five-membered rings, while two formyl groups are attached to the two nitrogen atoms of the six-membered ring. Due to caged structure of TNDFIW, the N—N (1.374–1.43 Å) bond length is much longer than that found in common nitramines (1.360 Å). The C—C bond lengths of TNDFIW (1.56–1.59 Å) are also much longer than normal C—C single bonds (1.54 Å). Bond angles in caged structures are also usually much larger than normal sp3 hybrid bond angles (Zarychta et al., 2005). There are a number of close intermolecular contacts less than the van der Waals radii, such as O1···O3 (2.827 Å), O6···O8 (2.853 Å), O2···O4 (2.891 Å); O2···N9 (2.895 Å), and O8···N9 (2.746 Å). From the above analysis, we know that TNDFIW has high tensile force and energy.

Related literature top

For the synthesis, structure and properties of a related compound, see: Keshavarz et al. (2009); Liu et al. (2006); Ou et al. (2000); Jin et al. (2009). For sp³ bond angles, see: Zarychta et al. (2005).

Experimental top

Due to the higher electronic density of five-membered rings than six-membered rings, N atoms on the 2, 6, 8, 12-positions of the two five-membered rings are more reactive than the N atoms on the 8 and 10-positions of the six-membered ring. Therefore, the four acetyls on on the five-membered rings are cleaved first and replaced by nitro groups in the nitrolysis of TADFIW with mixed sulfuric and nitric acids as the nitrating agent.

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 40 ⁰C, tetraacetyl-diformylhexaazaisowurtzitane (10 g) was added, and then the temperature was elevated to 45 ⁰C. The solution was maintained at 45 ⁰C for 8 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 numbers of nitro substitutes.

Pure TNDFIW was obtained using silica column chromatography with hexane/acetyl acetate (6/4 by volume) as the mobile phase at room temperature (25 ⁰C). Pure TNDFIW was dissolved in dry acetyl acetate, and then several drops of hexane was added. The resulting solution wasallowed to sit at ambient conditions (15–20 ^oC). A week later, single crystals was obtained by controlling the evaporation of the solvent. Element analysis, FT—IR, MS and ¹H NMR were in agreement with the structure of TNDFIW.

Structure description top

For the synthesis, structure and properties of a related compound, see: Keshavarz et al. (2009); Liu et al. (2006); Ou et al. (2000); Jin et al. (2009). For sp³ bond angles, see: Zarychta et al. (2005).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of PTNDFIW, with displacement ellipsoids drawn at the 50% probability level.

4,10-Diformyl-2,6,8,12-tetranitro-2,4,6,8,10,12- hexaazatetracyclo[5.5.0.0^5,9.0^3,11]dodecane top

Crystal data top

C₈H₈N₁₀O₁₀	F(000) = 824
M_r = 404.24	D_x = 1.891 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4366 reflections
a = 8.7794 (15) Å	θ = 3.2–27.5°
b = 12.715 (2) Å	µ = 0.17 mm⁻¹
c = 12.716 (2) Å	T = 93 K
V = 1419.6 (4) Å³	Prism, colorless
Z = 4	0.20 × 0.13 × 0.09 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	1786 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.047
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
Detector resolution: 28.5714 pixels mm^-1	h = −11→11
Multi–scan	k = −16→15
11584 measured reflections	l = −16→16
1866 independent reflections

Refinement top

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0526P)² + 0.616P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
1866 reflections	Δρ_max = 0.25 e Å⁻³
254 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0059 (19)

Crystal data top

C₈H₈N₁₀O₁₀	V = 1419.6 (4) Å³
M_r = 404.24	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.7794 (15) Å	µ = 0.17 mm⁻¹
b = 12.715 (2) Å	T = 93 K
c = 12.716 (2) Å	0.20 × 0.13 × 0.09 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	1786 reflections with I > 2σ(I)
11584 measured reflections	R_int = 0.047
1866 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.00	Δρ_max = 0.25 e Å⁻³
1866 reflections	Δρ_min = −0.22 e Å⁻³
254 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.4082 (3)	0.85128 (17)	0.61717 (16)	0.0240 (5)
O2	0.3469 (3)	0.90661 (16)	0.77458 (17)	0.0216 (5)
O3	0.0964 (3)	0.53590 (17)	0.52348 (15)	0.0199 (5)
O4	−0.0683 (2)	0.49964 (16)	0.64766 (17)	0.0211 (5)
O5	0.6678 (2)	0.63739 (16)	0.65467 (17)	0.0210 (5)
O6	0.6745 (2)	0.61863 (16)	0.82517 (17)	0.0209 (5)
O7	0.4006 (3)	0.41001 (17)	0.57581 (16)	0.0233 (5)
O8	0.3173 (3)	0.33820 (16)	0.72066 (18)	0.0256 (5)
O9	0.4078 (2)	0.73460 (18)	1.03162 (16)	0.0227 (5)
O10	0.0492 (3)	0.40004 (17)	0.91506 (17)	0.0239 (5)
N1	0.2201 (3)	0.77417 (18)	0.70425 (19)	0.0156 (5)
N2	0.0774 (3)	0.64219 (18)	0.66086 (18)	0.0143 (5)
N3	0.4504 (3)	0.65013 (19)	0.74559 (18)	0.0149 (5)
N4	0.2978 (3)	0.51090 (18)	0.70091 (18)	0.0143 (5)
N5	0.2786 (3)	0.70758 (17)	0.87793 (18)	0.0142 (5)
N6	0.1089 (3)	0.55208 (18)	0.82910 (18)	0.0149 (5)
N7	0.3337 (3)	0.84824 (18)	0.69836 (19)	0.0177 (5)
N8	0.0326 (3)	0.55254 (19)	0.60750 (19)	0.0163 (5)
N9	0.6093 (3)	0.63184 (18)	0.7414 (2)	0.0164 (5)
N10	0.3446 (3)	0.41296 (19)	0.66374 (19)	0.0179 (5)
C1	0.2262 (3)	0.6855 (2)	0.6321 (2)	0.0152 (6)
H1	0.2281	0.7093	0.5572	0.018*
C2	0.1599 (3)	0.7422 (2)	0.8080 (2)	0.0166 (6)
H2	0.0984	0.7998	0.8404	0.020*
C3	0.0559 (3)	0.6462 (2)	0.7767 (2)	0.0147 (6)
H3	−0.0530	0.6606	0.7947	0.018*
C4	0.3630 (3)	0.6075 (2)	0.6572 (2)	0.0148 (6)
H4	0.4281	0.5937	0.5942	0.018*
C5	0.3705 (3)	0.6206 (2)	0.8431 (2)	0.0146 (6)
H5	0.4451	0.5999	0.8989	0.018*
C6	0.2672 (3)	0.5255 (2)	0.8130 (2)	0.0148 (6)
H6	0.2958	0.4613	0.8540	0.018*
C7	0.3069 (4)	0.7593 (2)	0.9714 (2)	0.0190 (6)
H7	0.2439	0.8173	0.9895	0.023*
C8	0.0109 (4)	0.4835 (2)	0.8771 (2)	0.0195 (6)
H8	−0.0937	0.5025	0.8810	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0279 (12)	0.0256 (11)	0.0184 (10)	−0.0046 (10)	0.0081 (9)	0.0027 (9)
O2	0.0257 (12)	0.0141 (9)	0.0251 (11)	−0.0016 (9)	−0.0003 (9)	−0.0051 (9)
O3	0.0234 (12)	0.0236 (10)	0.0127 (9)	0.0024 (9)	0.0006 (9)	−0.0024 (8)
O4	0.0173 (11)	0.0193 (10)	0.0266 (11)	−0.0033 (9)	0.0003 (9)	−0.0016 (9)
O5	0.0170 (11)	0.0245 (11)	0.0217 (11)	0.0005 (9)	0.0064 (9)	−0.0007 (9)
O6	0.0191 (11)	0.0209 (10)	0.0226 (11)	0.0008 (9)	−0.0067 (9)	−0.0013 (8)
O7	0.0289 (12)	0.0235 (11)	0.0175 (10)	0.0060 (11)	0.0033 (9)	−0.0041 (9)
O8	0.0360 (14)	0.0130 (10)	0.0278 (12)	0.0012 (10)	0.0008 (11)	0.0026 (9)
O9	0.0232 (11)	0.0282 (11)	0.0167 (10)	−0.0023 (10)	−0.0049 (9)	−0.0026 (9)
O10	0.0285 (12)	0.0212 (11)	0.0221 (11)	−0.0076 (10)	−0.0001 (10)	0.0030 (9)
N1	0.0186 (12)	0.0131 (10)	0.0151 (11)	−0.0028 (10)	0.0005 (10)	−0.0001 (9)
N2	0.0156 (12)	0.0135 (11)	0.0136 (11)	−0.0018 (10)	−0.0010 (10)	−0.0035 (9)
N3	0.0118 (12)	0.0176 (11)	0.0152 (11)	0.0000 (10)	−0.0005 (10)	−0.0005 (9)
N4	0.0164 (12)	0.0116 (10)	0.0148 (11)	0.0008 (10)	0.0020 (9)	−0.0007 (9)
N5	0.0161 (12)	0.0137 (11)	0.0129 (11)	−0.0010 (9)	−0.0006 (10)	−0.0015 (9)
N6	0.0158 (12)	0.0142 (11)	0.0146 (11)	−0.0004 (9)	−0.0015 (10)	0.0025 (9)
N7	0.0169 (13)	0.0144 (11)	0.0218 (12)	0.0020 (10)	−0.0007 (11)	0.0021 (10)
N8	0.0176 (12)	0.0152 (11)	0.0161 (11)	0.0004 (10)	−0.0039 (10)	−0.0001 (9)
N9	0.0146 (12)	0.0128 (11)	0.0217 (12)	−0.0002 (10)	0.0014 (10)	−0.0017 (10)
N10	0.0203 (13)	0.0150 (11)	0.0184 (12)	0.0043 (10)	−0.0023 (11)	−0.0015 (10)
C1	0.0178 (14)	0.0135 (12)	0.0144 (13)	−0.0016 (11)	0.0009 (11)	0.0014 (10)
C2	0.0199 (15)	0.0145 (13)	0.0154 (13)	0.0006 (12)	−0.0001 (12)	−0.0004 (11)
C3	0.0132 (13)	0.0162 (13)	0.0146 (12)	0.0006 (11)	−0.0011 (11)	0.0011 (11)
C4	0.0174 (14)	0.0135 (12)	0.0134 (13)	0.0018 (11)	0.0000 (11)	−0.0008 (11)
C5	0.0141 (14)	0.0182 (13)	0.0116 (12)	0.0002 (11)	0.0005 (11)	0.0007 (10)
C6	0.0147 (14)	0.0173 (13)	0.0125 (13)	−0.0005 (11)	−0.0018 (11)	−0.0002 (10)
C7	0.0218 (15)	0.0174 (13)	0.0178 (14)	−0.0035 (12)	0.0014 (12)	−0.0040 (12)
C8	0.0211 (15)	0.0217 (15)	0.0156 (13)	−0.0087 (13)	−0.0013 (12)	0.0005 (12)

Geometric parameters (Å, º) top

O1—N7	1.223 (3)	N4—C6	1.462 (4)
O2—N7	1.226 (3)	N4—C4	1.464 (3)
O3—N8	1.225 (3)	N5—C7	1.381 (4)
O4—N8	1.224 (3)	N5—C5	1.439 (3)
O5—N9	1.218 (3)	N5—C2	1.439 (4)
O6—N9	1.221 (3)	N6—C8	1.369 (4)
O7—N10	1.222 (3)	N6—C6	1.445 (4)
O8—N10	1.219 (3)	N6—C3	1.446 (4)
O9—C7	1.212 (3)	C1—C4	1.590 (4)
O10—C8	1.213 (4)	C1—H1	1.0000
N1—N7	1.374 (3)	C2—C3	1.575 (4)
N1—C1	1.454 (3)	C2—H2	1.0000
N1—C2	1.478 (4)	C3—H3	1.0000
N2—N8	1.384 (3)	C4—H4	1.0000
N2—C1	1.464 (4)	C5—C6	1.559 (4)
N2—C3	1.486 (3)	C5—H5	1.0000
N3—N9	1.415 (3)	C6—H6	1.0000
N3—C4	1.465 (3)	C7—H7	0.9500
N3—C5	1.474 (3)	C8—H8	0.9500
N4—N10	1.394 (3)

N7—N1—C1	118.1 (2)	N5—C2—N1	112.1 (2)
N7—N1—C2	119.8 (2)	N5—C2—C3	109.8 (2)
C1—N1—C2	111.3 (2)	N1—C2—C3	101.3 (2)
N8—N2—C1	116.2 (2)	N5—C2—H2	111.1
N8—N2—C3	118.6 (2)	N1—C2—H2	111.1
C1—N2—C3	110.4 (2)	C3—C2—H2	111.1
N9—N3—C4	115.3 (2)	N6—C3—N2	112.8 (2)
N9—N3—C5	117.3 (2)	N6—C3—C2	109.8 (2)
C4—N3—C5	107.6 (2)	N2—C3—C2	101.7 (2)
N10—N4—C6	119.9 (2)	N6—C3—H3	110.7
N10—N4—C4	120.4 (2)	N2—C3—H3	110.7
C6—N4—C4	109.6 (2)	C2—C3—H3	110.7
C7—N5—C5	122.0 (2)	N4—C4—N3	102.9 (2)
C7—N5—C2	121.1 (2)	N4—C4—C1	107.7 (2)
C5—N5—C2	116.8 (2)	N3—C4—C1	108.6 (2)
C8—N6—C6	121.3 (2)	N4—C4—H4	112.4
C8—N6—C3	122.0 (2)	N3—C4—H4	112.4
C6—N6—C3	116.0 (2)	C1—C4—H4	112.4
O1—N7—O2	126.7 (2)	N5—C5—N3	109.3 (2)
O1—N7—N1	117.1 (2)	N5—C5—C6	110.2 (2)
O2—N7—N1	116.1 (2)	N3—C5—C6	105.5 (2)
O4—N8—O3	126.9 (3)	N5—C5—H5	110.6
O4—N8—N2	117.0 (2)	N3—C5—H5	110.6
O3—N8—N2	116.1 (2)	C6—C5—H5	110.6
O5—N9—O6	126.9 (2)	N6—C6—N4	110.2 (2)
O5—N9—N3	116.1 (2)	N6—C6—C5	110.1 (2)
O6—N9—N3	116.8 (2)	N4—C6—C5	103.4 (2)
O8—N10—O7	126.8 (3)	N6—C6—H6	111.0
O8—N10—N4	115.9 (2)	N4—C6—H6	111.0
O7—N10—N4	117.1 (2)	C5—C6—H6	111.0
N1—C1—N2	95.8 (2)	O9—C7—N5	123.5 (3)
N1—C1—C4	112.6 (2)	O9—C7—H7	118.2
N2—C1—C4	112.9 (2)	N5—C7—H7	118.2
N1—C1—H1	111.5	O10—C8—N6	124.1 (3)
N2—C1—H1	111.5	O10—C8—H8	118.0
C4—C1—H1	111.5	N6—C8—H8	118.0

C1—N1—N7—O1	19.1 (3)	N5—C2—C3—N6	1.0 (3)
C2—N1—N7—O1	160.2 (3)	N1—C2—C3—N6	119.7 (2)
C1—N1—N7—O2	−162.8 (2)	N5—C2—C3—N2	−118.7 (2)
C2—N1—N7—O2	−21.7 (4)	N1—C2—C3—N2	0.0 (3)
C1—N2—N8—O4	161.1 (2)	N10—N4—C4—N3	−112.6 (3)
C3—N2—N8—O4	25.9 (4)	C6—N4—C4—N3	32.6 (3)
C1—N2—N8—O3	−20.4 (3)	N10—N4—C4—C1	132.8 (3)
C3—N2—N8—O3	−155.6 (2)	C6—N4—C4—C1	−82.0 (3)
C4—N3—N9—O5	38.0 (3)	N9—N3—C4—N4	100.9 (3)
C5—N3—N9—O5	166.3 (2)	C5—N3—C4—N4	−32.1 (3)
C4—N3—N9—O6	−146.3 (2)	N9—N3—C4—C1	−145.1 (2)
C5—N3—N9—O6	−18.0 (3)	C5—N3—C4—C1	81.9 (3)
C6—N4—N10—O8	19.8 (4)	N1—C1—C4—N4	108.5 (2)
C4—N4—N10—O8	161.4 (3)	N2—C1—C4—N4	1.3 (3)
C6—N4—N10—O7	−164.2 (3)	N1—C1—C4—N3	−2.3 (3)
C4—N4—N10—O7	−22.5 (4)	N2—C1—C4—N3	−109.5 (3)
N7—N1—C1—N2	−173.1 (2)	C7—N5—C5—N3	−115.4 (3)
C2—N1—C1—N2	42.6 (3)	C2—N5—C5—N3	61.5 (3)
N7—N1—C1—C4	69.1 (3)	C7—N5—C5—C6	129.1 (3)
C2—N1—C1—C4	−75.2 (3)	C2—N5—C5—C6	−54.0 (3)
N8—N2—C1—N1	179.2 (2)	N9—N3—C5—N5	130.0 (2)
C3—N2—C1—N1	−42.1 (3)	C4—N3—C5—N5	−98.1 (3)
N8—N2—C1—C4	−63.2 (3)	N9—N3—C5—C6	−111.5 (3)
C3—N2—C1—C4	75.4 (3)	C4—N3—C5—C6	20.4 (3)
C7—N5—C2—N1	118.5 (3)	C8—N6—C6—N4	111.2 (3)
C5—N5—C2—N1	−58.4 (3)	C3—N6—C6—N4	−58.9 (3)
C7—N5—C2—C3	−129.8 (3)	C8—N6—C6—C5	−135.4 (3)
C5—N5—C2—C3	53.4 (3)	C3—N6—C6—C5	54.4 (3)
N7—N1—C2—N5	−54.2 (3)	N10—N4—C6—N6	−117.0 (3)
C1—N1—C2—N5	89.3 (3)	C4—N4—C6—N6	97.6 (3)
N7—N1—C2—C3	−171.2 (2)	N10—N4—C6—C5	125.5 (3)
C1—N1—C2—C3	−27.7 (3)	C4—N4—C6—C5	−19.9 (3)
C8—N6—C3—N2	−112.2 (3)	N5—C5—C6—N6	−0.2 (3)
C6—N6—C3—N2	57.9 (3)	N3—C5—C6—N6	−118.1 (2)
C8—N6—C3—C2	135.2 (3)	N5—C5—C6—N4	117.4 (2)
C6—N6—C3—C2	−54.7 (3)	N3—C5—C6—N4	−0.4 (3)
N8—N2—C3—N6	47.3 (3)	C5—N5—C7—O9	−1.5 (4)
C1—N2—C3—N6	−90.3 (3)	C2—N5—C7—O9	−178.2 (3)
N8—N2—C3—C2	164.8 (2)	C6—N6—C8—O10	4.8 (4)
C1—N2—C3—C2	27.2 (3)	C3—N6—C8—O10	174.3 (3)

Experimental details

Crystal data
Chemical formula	C₈H₈N₁₀O₁₀
M_r	404.24
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	93
a, b, c (Å)	8.7794 (15), 12.715 (2), 12.716 (2)
V (Å³)	1419.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.20 × 0.13 × 0.09

Data collection
Diffractometer	Rigaku AFC10/Saturn724+
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11584, 1866, 1786
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.094, 1.00
No. of reflections	1866
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Zarychta, B., Daszkiewicz, Z. & Zaleski, J. (2005). Acta Cryst. E61, o1897–o1899. Web of Science CSD CrossRef IUCr Journals 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
Keshavarz, M. H., Zali, A. & Shokrolahi, A. (2009). J. Hazard. Mater. 166, 1115–1119. Web of Science CrossRef PubMed CAS Google Scholar
Liu, J., Jin, S. & Shu, Q. (2006). Chin. J. Ener. Mater. 14, 346–349. CAS 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.