1,3,5-Trinitro-2,4-bis­(2-phenyl­ethen­yl)benzene

Guo, Z.-R.; Li, H.-B.; Li, F.

doi:10.1107/S1600536810034732

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2486

doi:10.1107/S1600536810034732

Open

access

1,3,5-Trinitro-2,4-bis(2-phenylethenyl)benzene

Ze-Rong Guo,^a ^* Hua-Bo Li ^a and Fang Li ^a

^aState Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: guozr531408@sohu.com

(Received 25 August 2010; accepted 28 August 2010; online 4 September 2010)

In the title compound, C₂₂H₁₅N₃O₆, the central benzene ring and one of the phenyl rings are essentially parallel to each other, making a dihedral angle of 1.35 (16)°. The dihedral angle between the two phenyl rings is 83.56 (19)°. Intramolecular C—H⋯N and C—H⋯O hydrogen bonds occur. In the crystal, molecules are linked through C—H⋯O hydrogen bonds. Furthermore, offset face-to-face π–π interactions with centroid–centroid distances of 3.644 (2) Å help to stabilize the crystal structure.

Related literature

For the preparation, see: Peng et al. (1995 ). For general background to trinitrobenzene and its derivatives, see: Ott & Benziger (1987 ); Kuperman et al. (2006 ). The title compound may be useful as a high energy explosive, see: Peng et al. (1995). For a related structure, see: Bryden (1972 ).

Experimental

Crystal data

C₂₂H₁₅N₃O₆
M_r = 417.37
Triclinic, $[P \overline 1]$
a = 7.0762 (14) Å
b = 8.6625 (17) Å
c = 16.717 (3) Å
α = 101.660 (3)°
β = 92.616 (3)°
γ = 105.122 (3)°
V = 963.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.32 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.577, T_max = 1.000
5265 measured reflections
3363 independent reflections
2146 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.236
S = 0.98
3363 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2	0.93	2.60	3.398 (4)	144
C16—H16⋯N1	0.93	2.42	2.980 (4)	119
C18—H18⋯O5ⁱ	0.93	2.48	3.387 (4)	166
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034732/wn2408sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810034732/wn2408Isup2.hkl

checkCIF report

Comment top

Trinitrobenzene and its derivatives have been extensively reported for use as energetic materials (Ott & Benziger, 1987; Kuperman et al., 2006). The title compound may be useful as a high energy explosive (Peng et al., 1995), and here we present its crystal structure.

In the title compound (Fig. 1), the bond distances and bond angles are similar to those in 2,4,6-trintro-m-xylene (Bryden, 1972). The planes of two rings (C9—C14) and (C17—C22) are approximately parallel, with a dihedral angle of 1.35 (16)°. The two phenyl rings, (C1—C6) and (C17—C22), form a dihedral angle of 83.56 (19)°. The short distance of 3.644 (2) Å (symmetry code: -x,-y,1 - z) between the centroids of the two parallel rings (C9—C14) and (C17—C22) indicates the existence of offset face-to-face π-π interactions. Molecules are linked through C—H···O hydrogen bonds (Table 1), which help to stabilize the crystal structure. Intramolecular C—H···N and C—H···O hydrogen bonds are also present. There is a short intermolecular contact C15···C15 (1-x, -y, 1-z) of 3.185 (4) Å.

Related literature top

For the preparation, see: Peng et al. (1995). For general background to trinitrobenzene and its derivatives, see: Ott & Benziger (1987); Kuperman et al. (2006). The title compound may be useful as a high energy explosive, see: Peng et al. (1995). For a related structure, see: Bryden (1972).

Experimental top

The title compound was synthesized using 2,4,6-trinitro-m-xylene and benzaldehyde as the starting materials, according to the literature method (Peng et al., 1995). Single crystals suitable for X–ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed along the a-axis. Intermolecular hydrogen bonds are shown as dashed lines.

1,3,5-Trinitro-2,4-bis(2-phenylethenyl)benzene top

Crystal data top

C₂₂H₁₅N₃O₆	Z = 2
M_r = 417.37	F(000) = 432
Triclinic, P1	D_x = 1.439 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0762 (14) Å	Cell parameters from 1118 reflections
b = 8.6625 (17) Å	θ = 2.5–22.8°
c = 16.717 (3) Å	µ = 0.11 mm⁻¹
α = 101.660 (3)°	T = 293 K
β = 92.616 (3)°	Block, colorless
γ = 105.122 (3)°	0.32 × 0.28 × 0.22 mm
V = 963.5 (3) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3363 independent reflections
Radiation source: fine-focus sealed tube	2146 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −8→8
T_min = 0.577, T_max = 1.000	k = −10→9
5265 measured reflections	l = −18→19

Refinement top

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.236	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.1716P)²] where P = (F_o² + 2F_c²)/3
3363 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₂H₁₅N₃O₆	γ = 105.122 (3)°
M_r = 417.37	V = 963.5 (3) Å³
Triclinic, P1	Z = 2
a = 7.0762 (14) Å	Mo Kα radiation
b = 8.6625 (17) Å	µ = 0.11 mm⁻¹
c = 16.717 (3) Å	T = 293 K
α = 101.660 (3)°	0.32 × 0.28 × 0.22 mm
β = 92.616 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3363 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2146 reflections with I > 2σ(I)
T_min = 0.577, T_max = 1.000	R_int = 0.020
5265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.236	H-atom parameters constrained
S = 0.98	Δρ_max = 0.66 e Å⁻³
3363 reflections	Δρ_min = −0.26 e Å⁻³
280 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	0.4557 (4)	0.2087 (3)	0.37673 (15)	0.0606 (7)
O2	0.1502 (4)	0.1919 (3)	0.34477 (15)	0.0629 (7)
O3	0.0777 (6)	−0.3754 (4)	0.12446 (17)	0.1042 (13)
O4	0.0663 (6)	−0.5709 (4)	0.18422 (17)	0.0944 (11)
O5	0.2954 (4)	−0.4565 (3)	0.47219 (15)	0.0599 (7)
O6	0.1092 (4)	−0.3227 (3)	0.53578 (14)	0.0558 (7)
N1	0.2829 (5)	0.1337 (3)	0.35892 (14)	0.0450 (7)
N2	0.0966 (4)	−0.4259 (4)	0.18514 (18)	0.0576 (8)
N3	0.2018 (4)	−0.3561 (3)	0.47819 (16)	0.0413 (6)
C1	0.5959 (7)	0.1705 (4)	0.0976 (2)	0.0659 (11)
H1	0.6973	0.1494	0.1272	0.079*
C2	0.6401 (8)	0.2529 (5)	0.0357 (2)	0.0796 (13)
H2	0.7691	0.2860	0.0230	0.096*
C3	0.4936 (11)	0.2845 (6)	−0.0061 (3)	0.0892 (16)
H3	0.5228	0.3398	−0.0482	0.107*
C4	0.3043 (10)	0.2385 (6)	0.0110 (3)	0.0914 (16)
H4	0.2057	0.2629	−0.0187	0.110*
C5	0.2581 (7)	0.1525 (5)	0.0745 (2)	0.0739 (12)
H5	0.1289	0.1199	0.0869	0.089*
C6	0.4058 (6)	0.1181 (4)	0.11752 (19)	0.0533 (9)
C7	0.3715 (6)	0.0306 (4)	0.18496 (19)	0.0502 (9)
H7	0.4820	0.0413	0.2202	0.060*
C8	0.2044 (5)	−0.0607 (4)	0.20150 (18)	0.0479 (8)
H8	0.0901	−0.0756	0.1677	0.057*
C9	0.1924 (4)	−0.1401 (4)	0.27196 (18)	0.0403 (7)
C10	0.1482 (5)	−0.3101 (4)	0.26559 (18)	0.0417 (8)
C11	0.1561 (4)	−0.3773 (4)	0.33316 (18)	0.0413 (8)
H11	0.1338	−0.4899	0.3271	0.050*
C12	0.1978 (4)	−0.2745 (3)	0.40967 (17)	0.0369 (7)
C13	0.2335 (4)	−0.1039 (3)	0.42426 (17)	0.0352 (7)
C14	0.2324 (4)	−0.0458 (3)	0.35209 (17)	0.0358 (7)
C15	0.2759 (4)	−0.0028 (3)	0.50832 (17)	0.0351 (7)
H15	0.3253	−0.0496	0.5470	0.042*
C16	0.2545 (4)	0.1434 (4)	0.53706 (17)	0.0390 (7)
H16	0.2098	0.1960	0.4999	0.047*
C17	0.2962 (4)	0.2302 (3)	0.62389 (17)	0.0367 (7)
C18	0.3403 (5)	0.3997 (4)	0.6440 (2)	0.0480 (8)
H18	0.3405	0.4570	0.6026	0.058*
C19	0.3838 (6)	0.4843 (4)	0.7246 (2)	0.0557 (9)
H19	0.4147	0.5982	0.7372	0.067*
C20	0.3820 (5)	0.4014 (4)	0.7870 (2)	0.0559 (9)
H20	0.4124	0.4589	0.8414	0.067*
C21	0.3350 (5)	0.2343 (4)	0.76815 (19)	0.0519 (9)
H21	0.3313	0.1781	0.8102	0.062*
C22	0.2930 (5)	0.1474 (4)	0.68758 (18)	0.0433 (8)
H22	0.2624	0.0335	0.6757	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0682 (18)	0.0454 (14)	0.0558 (15)	−0.0073 (13)	−0.0013 (12)	0.0152 (11)
O2	0.0861 (19)	0.0507 (15)	0.0599 (16)	0.0323 (14)	0.0044 (13)	0.0132 (12)
O3	0.180 (4)	0.072 (2)	0.0320 (16)	−0.007 (2)	−0.0013 (17)	0.0030 (14)
O4	0.155 (3)	0.0493 (18)	0.0638 (19)	0.0272 (18)	−0.0128 (18)	−0.0140 (14)
O5	0.0746 (17)	0.0522 (15)	0.0633 (16)	0.0263 (13)	0.0098 (12)	0.0245 (12)
O6	0.0698 (16)	0.0471 (14)	0.0498 (15)	0.0096 (12)	0.0190 (12)	0.0151 (11)
N1	0.0638 (19)	0.0409 (15)	0.0280 (14)	0.0108 (15)	0.0040 (12)	0.0074 (11)
N2	0.068 (2)	0.0486 (19)	0.0429 (18)	0.0054 (15)	0.0006 (14)	−0.0056 (14)
N3	0.0465 (16)	0.0338 (14)	0.0398 (15)	0.0042 (12)	0.0049 (12)	0.0084 (11)
C1	0.096 (3)	0.047 (2)	0.053 (2)	0.015 (2)	0.020 (2)	0.0127 (17)
C2	0.125 (4)	0.057 (3)	0.051 (2)	0.011 (3)	0.022 (3)	0.015 (2)
C3	0.159 (5)	0.058 (3)	0.046 (2)	0.019 (3)	0.017 (3)	0.014 (2)
C4	0.147 (5)	0.075 (3)	0.057 (3)	0.041 (3)	−0.009 (3)	0.017 (2)
C5	0.110 (3)	0.065 (3)	0.053 (2)	0.030 (2)	0.006 (2)	0.020 (2)
C6	0.086 (3)	0.0400 (18)	0.0337 (18)	0.0197 (18)	0.0083 (17)	0.0050 (14)
C7	0.069 (2)	0.048 (2)	0.0352 (18)	0.0197 (18)	0.0029 (15)	0.0086 (14)
C8	0.059 (2)	0.051 (2)	0.0295 (17)	0.0140 (17)	−0.0004 (14)	0.0042 (14)
C9	0.0413 (17)	0.0392 (17)	0.0362 (17)	0.0080 (13)	0.0004 (13)	0.0038 (13)
C10	0.0440 (18)	0.0400 (17)	0.0330 (16)	0.0072 (14)	0.0008 (13)	−0.0035 (13)
C11	0.0452 (18)	0.0293 (16)	0.0442 (18)	0.0058 (13)	0.0052 (14)	0.0019 (13)
C12	0.0367 (16)	0.0353 (16)	0.0368 (17)	0.0074 (12)	0.0032 (12)	0.0074 (13)
C13	0.0317 (16)	0.0353 (16)	0.0356 (16)	0.0074 (12)	0.0013 (12)	0.0042 (12)
C14	0.0377 (17)	0.0320 (15)	0.0344 (16)	0.0067 (12)	0.0027 (12)	0.0039 (12)
C15	0.0393 (17)	0.0313 (16)	0.0318 (15)	0.0043 (12)	−0.0002 (12)	0.0083 (12)
C16	0.0436 (18)	0.0398 (17)	0.0335 (16)	0.0118 (13)	0.0001 (13)	0.0083 (13)
C17	0.0361 (16)	0.0396 (17)	0.0317 (16)	0.0097 (13)	0.0021 (12)	0.0031 (13)
C18	0.065 (2)	0.0358 (17)	0.0421 (18)	0.0130 (15)	0.0056 (15)	0.0073 (14)
C19	0.078 (2)	0.0366 (18)	0.046 (2)	0.0108 (17)	0.0036 (17)	0.0008 (15)
C20	0.072 (2)	0.050 (2)	0.0381 (19)	0.0164 (18)	−0.0009 (16)	−0.0058 (16)
C21	0.070 (2)	0.057 (2)	0.0328 (17)	0.0241 (18)	0.0047 (15)	0.0125 (15)
C22	0.055 (2)	0.0367 (16)	0.0390 (17)	0.0126 (14)	0.0058 (14)	0.0087 (13)

Geometric parameters (Å, º) top

O1—N1	1.217 (3)	C8—H8	0.9300
O2—N1	1.211 (3)	C9—C14	1.394 (4)
O3—N2	1.199 (4)	C9—C10	1.404 (4)
O4—N2	1.214 (4)	C10—C11	1.376 (4)
O5—N3	1.216 (3)	C11—C12	1.372 (4)
O6—N3	1.218 (3)	C11—H11	0.9300
N1—C14	1.481 (4)	C12—C13	1.401 (4)
N2—C10	1.472 (4)	C13—C14	1.398 (4)
N3—C12	1.465 (4)	C13—C15	1.469 (4)
C1—C2	1.376 (5)	C15—C16	1.311 (4)
C1—C6	1.382 (5)	C15—H15	0.9300
C1—H1	0.9300	C16—C17	1.471 (4)
C2—C3	1.341 (7)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.385 (4)
C3—C4	1.356 (7)	C17—C22	1.397 (4)
C3—H3	0.9300	C18—C19	1.376 (4)
C4—C5	1.420 (6)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.379 (5)
C5—C6	1.370 (5)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.364 (5)
C6—C7	1.476 (5)	C20—H20	0.9300
C7—C8	1.315 (5)	C21—C22	1.381 (4)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.475 (4)	C22—H22	0.9300

O2—N1—O1	126.0 (3)	C9—C10—N2	121.2 (3)
O2—N1—C14	117.4 (3)	C12—C11—C10	118.6 (3)
O1—N1—C14	116.5 (3)	C12—C11—H11	120.7
O3—N2—O4	122.9 (3)	C10—C11—H11	120.7
O3—N2—C10	119.5 (3)	C11—C12—C13	124.4 (3)
O4—N2—C10	117.5 (3)	C11—C12—N3	115.1 (3)
O5—N3—O6	124.5 (3)	C13—C12—N3	120.5 (2)
O5—N3—C12	116.7 (3)	C14—C13—C12	113.1 (3)
O6—N3—C12	118.8 (2)	C14—C13—C15	126.0 (3)
C2—C1—C6	122.2 (4)	C12—C13—C15	120.9 (3)
C2—C1—H1	118.9	C9—C14—C13	126.6 (3)
C6—C1—H1	118.9	C9—C14—N1	114.9 (3)
C3—C2—C1	118.7 (5)	C13—C14—N1	118.4 (2)
C3—C2—H2	120.7	C16—C15—C13	129.8 (3)
C1—C2—H2	120.7	C16—C15—H15	115.1
C2—C3—C4	122.1 (5)	C13—C15—H15	115.1
C2—C3—H3	118.9	C15—C16—C17	124.7 (3)
C4—C3—H3	118.9	C15—C16—H16	117.7
C3—C4—C5	119.3 (5)	C17—C16—H16	117.7
C3—C4—H4	120.3	C18—C17—C22	118.3 (3)
C5—C4—H4	120.3	C18—C17—C16	119.5 (3)
C6—C5—C4	119.4 (5)	C22—C17—C16	122.2 (3)
C6—C5—H5	120.3	C19—C18—C17	120.8 (3)
C4—C5—H5	120.3	C19—C18—H18	119.6
C5—C6—C1	118.3 (4)	C17—C18—H18	119.6
C5—C6—C7	123.0 (4)	C18—C19—C20	120.4 (3)
C1—C6—C7	118.6 (3)	C18—C19—H19	119.8
C8—C7—C6	128.2 (3)	C20—C19—H19	119.8
C8—C7—H7	115.9	C21—C20—C19	119.4 (3)
C6—C7—H7	115.9	C21—C20—H20	120.3
C7—C8—C9	122.1 (3)	C19—C20—H20	120.3
C7—C8—H8	118.9	C20—C21—C22	120.9 (3)
C9—C8—H8	118.9	C20—C21—H21	119.5
C14—C9—C10	114.8 (3)	C22—C21—H21	119.5
C14—C9—C8	120.5 (3)	C21—C22—C17	120.1 (3)
C10—C9—C8	124.7 (3)	C21—C22—H22	120.0
C11—C10—C9	122.3 (3)	C17—C22—H22	120.0
C11—C10—N2	116.5 (3)

C6—C1—C2—C3	0.7 (6)	C11—C12—C13—C14	−3.0 (4)
C1—C2—C3—C4	0.2 (7)	N3—C12—C13—C14	177.4 (2)
C2—C3—C4—C5	−0.6 (7)	C11—C12—C13—C15	179.6 (3)
C3—C4—C5—C6	0.1 (6)	N3—C12—C13—C15	0.0 (4)
C4—C5—C6—C1	0.7 (5)	C10—C9—C14—C13	0.4 (5)
C4—C5—C6—C7	179.5 (4)	C8—C9—C14—C13	−177.6 (3)
C2—C1—C6—C5	−1.1 (5)	C10—C9—C14—N1	178.9 (3)
C2—C1—C6—C7	−180.0 (3)	C8—C9—C14—N1	0.8 (4)
C5—C6—C7—C8	18.2 (5)	C12—C13—C14—C9	2.8 (4)
C1—C6—C7—C8	−163.0 (4)	C15—C13—C14—C9	−179.9 (3)
C6—C7—C8—C9	−179.5 (3)	C12—C13—C14—N1	−175.6 (2)
C7—C8—C9—C14	65.4 (4)	C15—C13—C14—N1	1.7 (4)
C7—C8—C9—C10	−112.4 (4)	O2—N1—C14—C9	74.1 (3)
C14—C9—C10—C11	−3.9 (4)	O1—N1—C14—C9	−104.5 (3)
C8—C9—C10—C11	174.0 (3)	O2—N1—C14—C13	−107.4 (3)
C14—C9—C10—N2	178.0 (3)	O1—N1—C14—C13	74.1 (3)
C8—C9—C10—N2	−4.0 (5)	C14—C13—C15—C16	26.2 (5)
O3—N2—C10—C11	176.3 (3)	C12—C13—C15—C16	−156.8 (3)
O4—N2—C10—C11	−0.5 (5)	C13—C15—C16—C17	177.8 (3)
O3—N2—C10—C9	−5.6 (5)	C15—C16—C17—C18	156.0 (3)
O4—N2—C10—C9	177.7 (3)	C15—C16—C17—C22	−24.0 (5)
C9—C10—C11—C12	3.8 (5)	C22—C17—C18—C19	1.4 (5)
N2—C10—C11—C12	−178.1 (3)	C16—C17—C18—C19	−178.7 (3)
C10—C11—C12—C13	−0.1 (5)	C17—C18—C19—C20	−0.8 (5)
C10—C11—C12—N3	179.5 (3)	C18—C19—C20—C21	−0.5 (6)
O5—N3—C12—C11	47.8 (4)	C19—C20—C21—C22	1.2 (5)
O6—N3—C12—C11	−130.5 (3)	C20—C21—C22—C17	−0.6 (5)
O5—N3—C12—C13	−132.5 (3)	C18—C17—C22—C21	−0.7 (5)
O6—N3—C12—C13	49.1 (4)	C16—C17—C22—C21	179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2	0.93	2.60	3.398 (4)	144
C16—H16···N1	0.93	2.42	2.980 (4)	119
C18—H18···O5ⁱ	0.93	2.48	3.387 (4)	166

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅N₃O₆
M_r	417.37
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.0762 (14), 8.6625 (17), 16.717 (3)
α, β, γ (°)	101.660 (3), 92.616 (3), 105.122 (3)
V (Å³)	963.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.28 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.577, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5265, 3363, 2146
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.236, 0.98
No. of reflections	3363
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.26

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2	0.93	2.60	3.398 (4)	144
C16—H16···N1	0.93	2.42	2.980 (4)	119
C18—H18···O5ⁱ	0.93	2.48	3.387 (4)	166

Symmetry code: (i) x, y+1, z.

Acknowledgements

This work was supported by the State Key Laboratory of Explosion Science and Technology Foundation (YBKT09–10, SKLEST–ZZ–09–10), Beijing Institute of Technology.

References

Bruker (2002). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SADABS and SAINT-Plus. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Bryden, J. H. (1972). Acta Cryst. B28, 1395–1398. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kuperman, R. G., Checkai, R. T., Simini, M., Phillips, C. T., Kolakowski, J. E. & Kurnas, C. W. (2006). Environ. Toxicol. Chem. 25, 1368–1375. Web of Science CrossRef PubMed CAS Google Scholar
Ott, D. G. & Benziger, T. M. (1987). J. Energ. Mater, 5, 343–354. CrossRef CAS Google Scholar
Peng, X. H., Chen, T. Y., Lu, C. X. & Sun, R. K. (1995). Org. Prep. Proceed. Int. 27, 475–479. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar