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

Chen, H.; Li, L.; Liu, S.; Chen, S.; Jin, S.

doi:10.1107/S1600536810002813

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o452

https://doi.org/10.1107/S1600536810002813

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10-Formyl-2,4,6,8,12-pentanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0^5,9.0^3,11]dodecane acetone solvate

Huaxiong Chen,^a,^b Lijie Li,^a Sufen Liu,^a Shusen Chen ^a and Shaohua Jin ^a ^*

^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

(Received 10 January 2010; accepted 22 January 2010; online 27 January 2010)

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[5.5.0.0^5,9.0^3,11]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

C₇H₇N₁₁O₁₁·C₃H₆O
M_r = 479.31
Monoclinic, P 2₁
a = 10.432 (3) Å
b = 7.9230 (19) Å
c = 12.191 (3) Å
β = 113.493 (2)°
V = 924.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 93 K
0.60 × 0.27 × 0.17 mm

Data collection

Rigaku Saturn724+ diffractometer
7388 measured reflections
2257 independent reflections
2056 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.066
S = 1.00
2257 reflections
301 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810002813/bg2324sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002813/bg2324Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 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 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 column chromatography 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 crystal structure of PNMFIW solvate was determined by single-crystal X-ray diffraction.

Structure description top

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).

Computing details top

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

Figures top

Fig. 1. Molecular structure of PNMFIW-acetone with labelling and displacement ellipsoids drawn at the 30% probability level.

10-Formyl-2,4,6,8,12-pentanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0^5,9.0^3,11]dodecane acetone solvate top

Crystal data top

C₇H₇N₁₁O₁₁·C₃H₆O	F(000) = 492
M_r = 479.31	D_x = 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

Data collection top

Rigaku Saturn724+ diffractometer	2056 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.033
Graphite monochromator	θ_max = 27.5°, θ_min = 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 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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0252P)² + 0.266P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2257 reflections	Δρ_max = 0.37 e Å⁻³
301 parameters	Δρ_min = −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)

Crystal data top

C₇H₇N₁₁O₁₁·C₃H₆O	V = 924.1 (4) Å³
M_r = 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)°

Data collection top

Rigaku Saturn724+ diffractometer	2056 reflections with I > 2σ(I)
7388 measured reflections	R_int = 0.033
2257 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.066	H-atom parameters constrained
S = 1.00	Δρ_max = 0.37 e Å⁻³
2257 reflections	Δρ_min = −0.25 e Å⁻³
301 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	0.5840 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.25

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

References

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