10-Formyl-2,4,6,8,12-penta­nitro-2,4,6,8,10,12-hexa­azatetra­cyclo­[5.5.0.03,11.05,9]dodeca­ne

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

doi:10.1107/S1600536809047138

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3112

doi:10.1107/S1600536809047138

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10-Formyl-2,4,6,8,12-pentanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0^3,11.0^5,9]dodecane

Shaohua Jin,^a Shusen Chen,^a ^* Huaxiong Chen,^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: chx314@126.com

(Received 14 October 2009; accepted 7 November 2009; online 18 November 2009)

The title compound, C₇H₇N₁₁O₁₁ (PNMFIW), is a caged heterocycle substituted with five nitro and one 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 a nitro group and a formyl are attached to the two N atoms of the six-membered ring.

Related literature

The title compound (PNMFIW) was reported as a by-product in the synthesis of hexanitrohexaazawurtzitane (HNIW), see: Golfier et al. (1998 ). Liu et al. (2006 ). For quantum calculations on HNIW and PNMFIW, see: Wu et al. (2003 ). For factors affecting the detonation performance of energetic compounds, see: Singh & Felix (2003 ); Zeman & Krupka (2003 ).

Experimental

Crystal data

C₇H₇N₁₁O₁₁
M_r = 421.24
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.8000 (18) Å
b = 12.534 (2) Å
c = 12.829 (3) Å
V = 1415.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 93 K
0.33 × 0.30 × 0.20 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: none
11499 measured reflections
1865 independent reflections
1773 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 1.00
1865 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrystalClear (Rigaku, 2002 ); 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: 10.1107/S1600536809047138/nk2008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047138/nk2008Isup2.hkl

checkCIF report

Comment top

The title compound, pentanitromonoformylhexaazaisowurtzitane (PNMFIW), was reported as a by-product in the synthesis of hexanitrohexaazawurtzitane (HNIW) (Golfier et al., 1998; Liu et al.,2006). We theoretically studied PNMFIW with quantum calculation and found that PNMFIW has a similar crystal structure and density but lower sensitivity compared with HNIW (Wu et al., 2003). The crystal structure of an energetic compound is very important, because detonation performance such as detonation velocity and pressure, depends largely on density which is identified by its crystal structure, while the sensitivity closely correlates with the crystal structure (Singh et al., 2003; Zeman et al., 2003). To now, the crystal structure and properties of PNMFIW have not been reported. We synthesized PNMFIW through the nitrolysis of tetraacetyldiformylhexaazaisowurtzitane (TADFIW) in mixed nitric and sulfuric acids and obtained single crystals of PNMFIW by controlled evaporation.

The main geometric parameters of PNMFIW are listed in Tables 1 and 2, and the molecular structure is illustrated in Fig.1. The cage structure of PNMFIW 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 PNMFIW boat-shaped , while more stable conformation of six-membered ring is in the 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. Due to cage structure of PNMFIW the bond length of N—N (1.369–1.436 Å) is much longer than common nitramine (1.360 Å). The bond length of C—C (1.561–1.587 Å) of PNMFIW is also much longer than common C—C bond (1.54 Å). Bond angles of N(4)—C(5)—C(6) (112.7°), C(7)—N(1)—C(1)(122.2°) and C(2)—N(2)—C(3) (117.5°) on caged structure are much bigger than normal angle of sp³ hybrid bond. From the molecular structure analysis above, we know that PNMFIW molecule has high tensile force and energy.

Related literature top

The title compound (PNMFIW) was reported as a by-product in the synthesis of hexanitrohexaazawurtzitane (HNIW), see: Golfier et al. (1998). Liu et al. (2006). For quantum calculations on HNIW and PNMFIW, see: Wu et al. (2003). For factors affecting the detonation performance of energetic compounds, see: Singh & Felix (2003); Zeman & Krupka (2003).

Experimental top

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 °C, tetraacetyldiformylhexaazaisowurtzitane (10 g) was added, and then the temperature was elevated to 65 °C. The solution was maintained at 65 °C 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 column chromatography with hexane/acetyl acetate (6/4 by volume) as mobile phase at room temperature (25 °C).

Pure PNMFIW was dissolved in mixed solvents of acetone and n-hexane, and then the resulted solution was placed in ambient condition (288–293 K). A week later, single crystals was obtained by controlling the evaporation of solvent. Elemental analysis, FT—IR, MS and ¹H NMR are in agreement with the structure of PNMFIW.

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); 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 PNMFIW with displacement ellipsoids drawn at the 50% probability level.

10-Formyl-2,4,6,8,12-pentanitro-2,4,6,8,10,12- hexaazatetracyclo[5.5.0.0^3,11.0^5,9]dodecane top

Crystal data top

C₇H₇N₁₁O₁₁	D_x = 1.977 Mg m⁻³
M_r = 421.24	Melting point: 247 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5010 reflections
a = 8.8000 (18) Å	θ = 3.2–27.5°
b = 12.534 (2) Å	µ = 0.19 mm⁻¹
c = 12.829 (3) Å	T = 93 K
V = 1415.1 (5) Å³	Prism, colourless
Z = 4	0.33 × 0.30 × 0.20 mm
F(000) = 856

Data collection top

Rigaku Saturn724+ diffractometer	1773 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.036
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
Detector resolution: 28.5714 pixels mm^-1	h = −11→10
Multi–scan	k = −16→14
11499 measured reflections	l = −16→16
1865 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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0486P)² + 0.596P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
1865 reflections	Δρ_max = 0.36 e Å⁻³
263 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
10 constraints	Extinction coefficient: 0.0821 (10)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₇H₇N₁₁O₁₁	V = 1415.1 (5) Å³
M_r = 421.24	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.8000 (18) Å	µ = 0.19 mm⁻¹
b = 12.534 (2) Å	T = 93 K
c = 12.829 (3) Å	0.33 × 0.30 × 0.20 mm

Data collection top

Rigaku Saturn724+ diffractometer	1773 reflections with I > 2σ(I)
11499 measured reflections	R_int = 0.036
1865 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.00	Δρ_max = 0.36 e Å⁻³
1865 reflections	Δρ_min = −0.27 e Å⁻³
263 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. 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	0.4007 (2)	0.13038 (16)	0.12911 (15)	0.0191 (4)
O2	0.3409 (2)	0.08809 (15)	0.28944 (15)	0.0179 (4)
O3	0.1006 (2)	0.45094 (16)	0.01761 (14)	0.0191 (4)
O4	−0.0499 (2)	0.50366 (16)	0.14359 (15)	0.0199 (4)
O5	0.6743 (2)	0.34574 (17)	0.13169 (16)	0.0222 (5)
O6	0.6994 (2)	0.37181 (16)	0.29844 (16)	0.0202 (4)
O7	0.4174 (2)	0.56954 (17)	0.04576 (14)	0.0223 (5)
O8	0.3477 (2)	0.66003 (15)	0.18230 (16)	0.0216 (5)
O9	0.4369 (3)	0.28833 (17)	0.52530 (16)	0.0239 (5)
O10	−0.0814 (2)	0.51961 (18)	0.37613 (17)	0.0265 (5)
O11	0.1111 (2)	0.62630 (16)	0.38019 (17)	0.0248 (5)
N1	0.2231 (3)	0.22215 (17)	0.21233 (17)	0.0130 (4)
N2	0.0880 (2)	0.35693 (18)	0.16357 (16)	0.0126 (5)
N3	0.4655 (2)	0.34315 (18)	0.23254 (17)	0.0132 (5)
N4	0.3187 (3)	0.48471 (17)	0.18203 (17)	0.0128 (4)
N5	0.3024 (2)	0.30228 (17)	0.37498 (17)	0.0126 (4)
N6	0.1429 (3)	0.45977 (17)	0.32082 (17)	0.0135 (5)
N7	0.3299 (3)	0.14247 (17)	0.21021 (18)	0.0148 (5)
N8	0.0428 (3)	0.44415 (18)	0.10471 (17)	0.0155 (5)
N9	0.6262 (3)	0.35696 (18)	0.21936 (19)	0.0162 (5)
N10	0.3673 (3)	0.57783 (18)	0.13405 (18)	0.0158 (5)
N11	0.0508 (3)	0.54120 (18)	0.36035 (18)	0.0173 (5)
C1	0.2300 (3)	0.3052 (2)	0.1333 (2)	0.0128 (5)
H1	0.2235	0.2746	0.0614	0.015*
C2	0.1756 (3)	0.2665 (2)	0.31371 (19)	0.0124 (5)
H2	0.1133	0.2136	0.3534	0.015*
C3	0.0756 (3)	0.3640 (2)	0.27868 (19)	0.0132 (5)
H3	−0.0321	0.3556	0.3021	0.016*
C4	0.3729 (3)	0.3812 (2)	0.1456 (2)	0.0130 (5)
H4	0.4327	0.3871	0.0795	0.016*
C5	0.3971 (3)	0.3834 (2)	0.33015 (19)	0.0122 (5)
H5	0.4779	0.4058	0.3804	0.015*
C6	0.2991 (3)	0.4819 (2)	0.29537 (19)	0.0126 (5)
H6	0.3352	0.5493	0.3288	0.015*
C7	0.3332 (3)	0.2587 (2)	0.4713 (2)	0.0160 (6)
H7	0.2699	0.2028	0.4962	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0186 (10)	0.0190 (10)	0.0197 (9)	0.0025 (8)	0.0057 (8)	−0.0027 (8)
O2	0.0180 (10)	0.0136 (9)	0.0221 (9)	0.0009 (8)	−0.0018 (8)	0.0041 (8)
O3	0.0227 (11)	0.0224 (10)	0.0121 (8)	−0.0001 (9)	−0.0025 (8)	0.0020 (7)
O4	0.0164 (9)	0.0197 (10)	0.0237 (10)	0.0058 (8)	−0.0005 (9)	0.0022 (8)
O5	0.0185 (10)	0.0264 (11)	0.0217 (10)	−0.0001 (9)	0.0084 (9)	−0.0004 (9)
O6	0.0128 (9)	0.0199 (10)	0.0278 (11)	−0.0016 (8)	−0.0045 (8)	0.0039 (9)
O7	0.0298 (12)	0.0221 (10)	0.0150 (9)	−0.0062 (10)	0.0022 (8)	0.0041 (8)
O8	0.0288 (11)	0.0113 (9)	0.0247 (10)	−0.0010 (8)	−0.0034 (9)	−0.0003 (8)
O9	0.0279 (11)	0.0241 (11)	0.0196 (10)	0.0030 (10)	−0.0095 (9)	−0.0009 (8)
O10	0.0213 (11)	0.0316 (12)	0.0267 (10)	0.0032 (9)	0.0019 (9)	−0.0012 (10)
O11	0.0291 (12)	0.0140 (10)	0.0312 (11)	0.0037 (9)	−0.0051 (10)	−0.0073 (9)
N1	0.0127 (10)	0.0120 (10)	0.0142 (10)	0.0011 (9)	0.0016 (9)	−0.0004 (9)
N2	0.0143 (11)	0.0129 (11)	0.0105 (10)	0.0017 (9)	−0.0015 (8)	0.0006 (8)
N3	0.0081 (10)	0.0152 (11)	0.0161 (11)	−0.0009 (9)	0.0007 (8)	0.0000 (9)
N4	0.0164 (11)	0.0089 (10)	0.0132 (10)	−0.0019 (9)	0.0011 (9)	0.0007 (8)
N5	0.0113 (10)	0.0144 (11)	0.0123 (10)	−0.0008 (9)	−0.0014 (9)	0.0006 (8)
N6	0.0122 (11)	0.0132 (11)	0.0152 (10)	0.0015 (9)	0.0007 (9)	−0.0045 (9)
N7	0.0134 (11)	0.0111 (10)	0.0198 (11)	−0.0014 (9)	−0.0012 (9)	−0.0012 (9)
N8	0.0137 (11)	0.0167 (11)	0.0160 (11)	−0.0002 (9)	−0.0039 (9)	0.0012 (9)
N9	0.0117 (10)	0.0126 (11)	0.0242 (11)	−0.0011 (9)	0.0003 (10)	0.0038 (10)
N10	0.0174 (11)	0.0141 (11)	0.0159 (10)	−0.0025 (9)	−0.0029 (10)	0.0006 (9)
N11	0.0162 (11)	0.0187 (12)	0.0171 (11)	0.0058 (10)	−0.0012 (10)	0.0003 (9)
C1	0.0126 (12)	0.0125 (12)	0.0131 (11)	0.0003 (10)	−0.0036 (10)	−0.0011 (10)
C2	0.0121 (12)	0.0145 (12)	0.0107 (11)	0.0001 (10)	0.0015 (9)	−0.0018 (10)
C3	0.0121 (12)	0.0146 (12)	0.0129 (11)	0.0000 (10)	0.0011 (10)	−0.0003 (10)
C4	0.0117 (12)	0.0133 (12)	0.0139 (11)	0.0007 (10)	−0.0015 (10)	0.0001 (10)
C5	0.0108 (12)	0.0132 (12)	0.0126 (11)	−0.0007 (10)	−0.0008 (10)	−0.0011 (9)
C6	0.0119 (12)	0.0132 (12)	0.0127 (11)	0.0014 (10)	−0.0021 (10)	−0.0025 (10)
C7	0.0194 (14)	0.0139 (13)	0.0146 (12)	0.0015 (11)	−0.0012 (11)	0.0011 (11)

Geometric parameters (Å, º) top

O1—N7	1.222 (3)	N4—N10	1.387 (3)
O2—N7	1.228 (3)	N4—C4	1.460 (3)
O3—N8	1.231 (3)	N4—C6	1.465 (3)
O4—N8	1.212 (3)	N5—C7	1.378 (3)
O5—N9	1.210 (3)	N5—C5	1.435 (3)
O6—N9	1.216 (3)	N5—C2	1.436 (3)
O7—N10	1.220 (3)	N6—N11	1.398 (3)
O8—N10	1.214 (3)	N6—C6	1.440 (3)
O9—C7	1.205 (3)	N6—C3	1.444 (3)
O10—N11	1.211 (3)	C1—C4	1.586 (3)
O11—N11	1.218 (3)	C1—H1	1.0000
N1—N7	1.372 (3)	C2—C3	1.571 (4)
N1—C1	1.454 (3)	C2—H2	1.0000
N1—C2	1.475 (3)	C3—H3	1.0000
N2—N8	1.387 (3)	C4—H4	1.0000
N2—C1	1.460 (3)	C5—C6	1.570 (4)
N2—C3	1.483 (3)	C5—H5	1.0000
N3—N9	1.435 (3)	C6—H6	1.0000
N3—C4	1.461 (3)	C7—H7	0.9500
N3—C5	1.478 (3)

N7—N1—C1	118.6 (2)	N1—C1—H1	111.5
N7—N1—C2	119.1 (2)	N2—C1—H1	111.5
C1—N1—C2	110.9 (2)	C4—C1—H1	111.5
N8—N2—C1	116.8 (2)	N5—C2—N1	112.4 (2)
N8—N2—C3	118.3 (2)	N5—C2—C3	110.4 (2)
C1—N2—C3	110.7 (2)	N1—C2—C3	101.50 (19)
N9—N3—C4	114.8 (2)	N5—C2—H2	110.7
N9—N3—C5	117.4 (2)	N1—C2—H2	110.7
C4—N3—C5	108.0 (2)	C3—C2—H2	110.7
N10—N4—C4	120.3 (2)	N6—C3—N2	113.1 (2)
N10—N4—C6	119.8 (2)	N6—C3—C2	108.1 (2)
C4—N4—C6	109.6 (2)	N2—C3—C2	101.38 (19)
C7—N5—C5	121.7 (2)	N6—C3—H3	111.3
C7—N5—C2	121.3 (2)	N2—C3—H3	111.3
C5—N5—C2	116.9 (2)	C2—C3—H3	111.3
N11—N6—C6	119.7 (2)	N4—C4—N3	103.1 (2)
N11—N6—C3	120.4 (2)	N4—C4—C1	107.9 (2)
C6—N6—C3	117.8 (2)	N3—C4—C1	108.8 (2)
O1—N7—O2	126.6 (2)	N4—C4—H4	112.2
O1—N7—N1	117.2 (2)	N3—C4—H4	112.2
O2—N7—N1	116.2 (2)	C1—C4—H4	112.2
O4—N8—O3	127.5 (2)	N5—C5—N3	109.5 (2)
O4—N8—N2	117.0 (2)	N5—C5—C6	110.6 (2)
O3—N8—N2	115.5 (2)	N3—C5—C6	104.5 (2)
O5—N9—O6	127.5 (2)	N5—C5—H5	110.7
O5—N9—N3	116.1 (2)	N3—C5—H5	110.7
O6—N9—N3	116.2 (2)	C6—C5—H5	110.7
O8—N10—O7	126.7 (2)	N6—C6—N4	110.0 (2)
O8—N10—N4	116.4 (2)	N6—C6—C5	108.0 (2)
O7—N10—N4	116.9 (2)	N4—C6—C5	103.7 (2)
O10—N11—O11	125.4 (2)	N6—C6—H6	111.6
O10—N11—N6	117.0 (2)	N4—C6—H6	111.6
O11—N11—N6	117.6 (2)	C5—C6—H6	111.6
N1—C1—N2	95.6 (2)	O9—C7—N5	122.8 (3)
N1—C1—C4	113.2 (2)	O9—C7—H7	118.6
N2—C1—C4	112.7 (2)	N5—C7—H7	118.6

C1—N1—N7—O1	−17.6 (3)	C1—N2—C3—N6	88.6 (3)
C2—N1—N7—O1	−157.8 (2)	N8—N2—C3—C2	−165.5 (2)
C1—N1—N7—O2	164.7 (2)	C1—N2—C3—C2	−26.8 (3)
C2—N1—N7—O2	24.5 (3)	N5—C2—C3—N6	−0.7 (3)
C1—N2—N8—O4	−161.3 (2)	N1—C2—C3—N6	−120.0 (2)
C3—N2—N8—O4	−25.1 (3)	N5—C2—C3—N2	118.4 (2)
C1—N2—N8—O3	19.8 (3)	N1—C2—C3—N2	−0.9 (2)
C3—N2—N8—O3	156.0 (2)	N10—N4—C4—N3	112.9 (2)
C4—N3—N9—O5	−35.7 (3)	C6—N4—C4—N3	−32.2 (3)
C5—N3—N9—O5	−164.2 (2)	N10—N4—C4—C1	−132.1 (2)
C4—N3—N9—O6	148.8 (2)	C6—N4—C4—C1	82.8 (2)
C5—N3—N9—O6	20.3 (3)	N9—N3—C4—N4	−100.2 (2)
C4—N4—N10—O8	−163.1 (2)	C5—N3—C4—N4	32.8 (2)
C6—N4—N10—O8	−21.6 (3)	N9—N3—C4—C1	145.4 (2)
C4—N4—N10—O7	20.8 (3)	C5—N3—C4—C1	−81.5 (2)
C6—N4—N10—O7	162.4 (2)	N1—C1—C4—N4	−108.5 (2)
C6—N6—N11—O10	176.8 (2)	N2—C1—C4—N4	−1.5 (3)
C3—N6—N11—O10	13.9 (3)	N1—C1—C4—N3	2.7 (3)
C6—N6—N11—O11	−6.2 (3)	N2—C1—C4—N3	109.7 (2)
C3—N6—N11—O11	−169.1 (2)	C7—N5—C5—N3	117.4 (2)
N7—N1—C1—N2	173.7 (2)	C2—N5—C5—N3	−61.1 (3)
C2—N1—C1—N2	−43.1 (2)	C7—N5—C5—C6	−128.0 (2)
N7—N1—C1—C4	−68.7 (3)	C2—N5—C5—C6	53.5 (3)
C2—N1—C1—C4	74.5 (3)	N9—N3—C5—N5	−131.2 (2)
N8—N2—C1—N1	−178.4 (2)	C4—N3—C5—N5	97.1 (2)
C3—N2—C1—N1	42.3 (2)	N9—N3—C5—C6	110.3 (2)
N8—N2—C1—C4	63.6 (3)	C4—N3—C5—C6	−21.5 (3)
C3—N2—C1—C4	−75.7 (3)	N11—N6—C6—N4	−107.2 (3)
C7—N5—C2—N1	−119.4 (2)	C3—N6—C6—N4	56.2 (3)
C5—N5—C2—N1	59.1 (3)	N11—N6—C6—C5	140.3 (2)
C7—N5—C2—C3	128.1 (2)	C3—N6—C6—C5	−56.4 (3)
C5—N5—C2—C3	−53.4 (3)	N10—N4—C6—N6	118.3 (2)
N7—N1—C2—N5	53.7 (3)	C4—N4—C6—N6	−96.4 (2)
C1—N1—C2—N5	−89.3 (2)	N10—N4—C6—C5	−126.4 (2)
N7—N1—C2—C3	171.6 (2)	C4—N4—C6—C5	18.8 (3)
C1—N1—C2—C3	28.6 (3)	N5—C5—C6—N6	0.6 (3)
N11—N6—C3—N2	108.3 (3)	N3—C5—C6—N6	118.4 (2)
C6—N6—C3—N2	−54.9 (3)	N5—C5—C6—N4	−116.1 (2)
N11—N6—C3—C2	−140.3 (2)	N3—C5—C6—N4	1.7 (3)
C6—N6—C3—C2	56.4 (3)	C5—N5—C7—O9	3.0 (4)
N8—N2—C3—N6	−50.1 (3)	C2—N5—C7—O9	−178.6 (3)

Experimental details

Crystal data
Chemical formula	C₇H₇N₁₁O₁₁
M_r	421.24
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	93
a, b, c (Å)	8.8000 (18), 12.534 (2), 12.829 (3)
V (Å³)	1415.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.33 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11499, 1865, 1773
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 1.00
No. of reflections	1865
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.27

Computer programs: CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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