1-(4,5-Dinitro-10-aza­tricyclo­[6.3.1.02,7]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoro­ethanone

Xu, H.; Quan, J.-C.; Xu, J.; Chen, J.; Wang, J.-T.

doi:10.1107/S1600536808028158

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2425

doi:10.1107/S1600536808028158

Open

access

1-(4,5-Dinitro-10-azatricyclo[6.3.1.0^2,7]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoroethanone

Hao Xu,^a ^* Ji-Cai Quan,^a Jian Xu,^a Jing Chen ^a and Jin-Tang Wang ^a

^aCollege of Science, Nanjing University of Technolgy, Xinmofan Road No.5, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: cnjyc@sohu.com

(Received 29 August 2008; accepted 3 September 2008; online 22 November 2008)

In the title compound, C₁₃H₁₀F₃N₃O₅, a derivative of andrographolide, the five-membered ring adopts an envelope conformation, while the non-planar six-membered ring has a chair conformation. An intramolecular C—H⋯F hydrogen bond results in the formation of a non-planar six-membered ring adopting a twisted conformation. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For bond-length data, see: Allen et al. (1987 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₃H₁₀F₃N₃O₅
M_r = 345.24
Monoclinic, P 2₁ /c
a = 9.6400 (19) Å
b = 7.7430 (15) Å
c = 18.687 (4) Å
β = 96.98 (3)°
V = 1384.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 294 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.955, T_max = 0.985
2673 measured reflections
2513 independent reflections
1592 reflections with I > 2σ(I)
R_int = 0.052
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.183
S = 1.02
2513 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯F2	0.97	2.34	3.002 (6)	124
C9—H9A⋯O1ⁱ	0.93	2.41	3.338 (5)	173
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028158/hk2521sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028158/hk2521Isup2.hkl

checkCIF report

Comment top

Some derivatives of andrographolide are important chemical materials. We report herein the crystal structure of the title compound.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Ring A (C8–C13) is, of course, planar. Ring B (N1/C3–C7) is not planar, having total puckering amplitude, Q_T, of 0.626 (3) and chair conformation [ϕ = -175.64 (3)° and θ = 36.12 (3)°] (Cremer & Pople, 1975), while ring C (C4–C6/C8/C13) adopts envelope conformation, with C5 atom displaced by -0.707 (3) Å from the plane of the other ring atoms. The intramolecular C—H···F hydrogen bond (Table 1) results in the formation of a nonplanar six-membered ring D (F2/C1/C2/N1/C7/H7B), having total puckering amplitude, Q_T, of 0.651 (3) and twisted conformation [ϕ = 34.96 (3)° and θ = 76.80 (2)°] (Cremer & Pople, 1975)

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title compound, 1-(4,5-diamino-10-aza-tricyclo- [6.3.1.0]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoro-ethanone (3.0 g) was hydrogenated in methanol (30 ml, 95%) under hydrogen (45 psi) over Pd-carbon catalysts (300 mg of 20wt%/C,10%wt). After 2.5 h, the reaction was filtered through a celite pad and rinsed with methanol (30 ml, 95%). The solution was concentrated to a light brown oil that crystallized. An X-ray grade crystal of the title compound (500 mg) was grown from ethyl acetate (10 ml) at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

1-(4,5-Dinitro-10-azatricyclo[6.3.1.0^2,7]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoroethanone top

Crystal data top

C₁₃H₁₀F₃N₃O₅	F(000) = 704
M_r = 345.24	D_x = 1.656 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.6400 (19) Å	θ = 10–13°
b = 7.7430 (15) Å	µ = 0.15 mm⁻¹
c = 18.687 (4) Å	T = 294 K
β = 96.98 (3)°	Red, colorless
V = 1384.5 (5) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.052
Graphite monochromator	θ_max = 25.3°, θ_min = 2.1°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.955, T_max = 0.985	l = 0→22
2673 measured reflections	3 standard reflections every 120 min
2513 independent reflections	intensity decay: none

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.05P)² + 4P] where P = (F_o² + 2F_c²)/3
2513 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₃H₁₀F₃N₃O₅	V = 1384.5 (5) Å³
M_r = 345.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6400 (19) Å	µ = 0.15 mm⁻¹
b = 7.7430 (15) Å	T = 294 K
c = 18.687 (4) Å	0.30 × 0.20 × 0.10 mm
β = 96.98 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1592 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.052
T_min = 0.955, T_max = 0.985	3 standard reflections every 120 min
2673 measured reflections	intensity decay: none
2513 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.02	Δρ_max = 0.33 e Å⁻³
2513 reflections	Δρ_min = −0.35 e Å⁻³
217 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
F1	0.3302 (4)	0.7803 (5)	0.23330 (19)	0.1036 (13)
F2	0.1596 (3)	0.6268 (5)	0.25814 (17)	0.0907 (12)
F3	0.3030 (3)	0.5239 (4)	0.19179 (13)	0.0702 (9)
O1	0.4775 (4)	0.6527 (5)	0.34298 (19)	0.0681 (10)
O2	0.1222 (4)	0.4522 (5)	0.6478 (2)	0.0812 (12)
O3	0.0247 (4)	0.2030 (5)	0.65267 (18)	0.0733 (11)
O4	−0.2298 (3)	0.1740 (6)	0.4660 (2)	0.0772 (12)
O5	−0.1736 (4)	0.3629 (5)	0.5498 (2)	0.0749 (11)
N1	0.3630 (3)	0.3999 (5)	0.34108 (16)	0.0398 (8)
N2	0.0824 (4)	0.3155 (6)	0.6213 (2)	0.0512 (10)
N3	−0.1427 (4)	0.2615 (5)	0.5031 (2)	0.0532 (10)
C1	0.2916 (5)	0.6217 (7)	0.2505 (2)	0.0557 (12)
C2	0.3865 (4)	0.5564 (6)	0.3165 (2)	0.0446 (10)
C3	0.4621 (4)	0.3471 (7)	0.4042 (2)	0.0486 (11)
H3A	0.4714	0.4406	0.4390	0.058*
H3B	0.5532	0.3272	0.3887	0.058*
C4	0.4159 (4)	0.1853 (6)	0.4403 (2)	0.0442 (10)
H4A	0.4872	0.1443	0.4784	0.053*
C5	0.3737 (5)	0.0456 (7)	0.3846 (3)	0.0569 (12)
H5A	0.3600	−0.0649	0.4072	0.068*
H5B	0.4419	0.0331	0.3509	0.068*
C6	0.2364 (4)	0.1203 (6)	0.3485 (2)	0.0476 (11)
H6A	0.1799	0.0323	0.3208	0.057*
C7	0.2679 (5)	0.2734 (7)	0.3008 (2)	0.0524 (12)
H7A	0.3105	0.2310	0.2598	0.063*
H7B	0.1811	0.3304	0.2827	0.063*
C8	0.2766 (4)	0.2163 (5)	0.4683 (2)	0.0393 (9)
C9	0.2468 (4)	0.2693 (5)	0.5352 (2)	0.0398 (10)
H9A	0.3181	0.2968	0.5715	0.048*
C10	0.1095 (4)	0.2805 (5)	0.5470 (2)	0.0391 (9)
C11	0.0006 (4)	0.2439 (5)	0.4922 (2)	0.0381 (9)
C12	0.0337 (4)	0.1944 (6)	0.4239 (2)	0.0417 (10)
H12A	−0.0365	0.1737	0.3861	0.050*
C13	0.1695 (4)	0.1778 (5)	0.4143 (2)	0.0418 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.150 (3)	0.070 (2)	0.083 (2)	0.000 (2)	−0.017 (2)	0.0327 (19)
F2	0.0614 (19)	0.134 (3)	0.076 (2)	0.042 (2)	0.0060 (15)	0.020 (2)
F3	0.0736 (19)	0.102 (2)	0.0356 (14)	0.0003 (17)	0.0089 (12)	−0.0006 (15)
O1	0.072 (2)	0.053 (2)	0.074 (2)	−0.0176 (19)	−0.0145 (18)	0.0037 (18)
O2	0.100 (3)	0.075 (3)	0.068 (2)	−0.011 (2)	0.005 (2)	−0.030 (2)
O3	0.095 (3)	0.076 (3)	0.056 (2)	−0.005 (2)	0.0403 (19)	0.009 (2)
O4	0.0338 (17)	0.108 (3)	0.087 (3)	−0.016 (2)	−0.0066 (17)	−0.001 (2)
O5	0.054 (2)	0.078 (3)	0.098 (3)	0.0127 (19)	0.029 (2)	−0.007 (2)
N1	0.0348 (17)	0.053 (2)	0.0291 (16)	−0.0060 (16)	−0.0073 (13)	−0.0019 (15)
N2	0.050 (2)	0.056 (3)	0.045 (2)	0.007 (2)	−0.0007 (17)	−0.003 (2)
N3	0.043 (2)	0.055 (3)	0.060 (2)	0.0015 (19)	0.0023 (19)	0.018 (2)
C1	0.054 (3)	0.067 (3)	0.046 (3)	0.004 (3)	0.008 (2)	0.014 (2)
C2	0.045 (2)	0.051 (3)	0.039 (2)	0.002 (2)	0.0101 (18)	0.007 (2)
C3	0.033 (2)	0.069 (3)	0.042 (2)	−0.007 (2)	−0.0008 (17)	0.009 (2)
C4	0.033 (2)	0.058 (3)	0.042 (2)	0.007 (2)	0.0055 (17)	0.010 (2)
C5	0.061 (3)	0.052 (3)	0.063 (3)	0.004 (2)	0.027 (2)	0.003 (2)
C6	0.049 (2)	0.053 (3)	0.041 (2)	−0.013 (2)	0.0063 (19)	−0.007 (2)
C7	0.053 (3)	0.071 (3)	0.033 (2)	−0.016 (2)	0.0025 (19)	−0.009 (2)
C8	0.041 (2)	0.038 (2)	0.037 (2)	0.0014 (18)	−0.0044 (17)	0.0045 (18)
C9	0.036 (2)	0.045 (2)	0.034 (2)	−0.0047 (19)	−0.0095 (16)	0.0003 (18)
C10	0.041 (2)	0.039 (2)	0.035 (2)	−0.0009 (18)	−0.0026 (17)	0.0051 (18)
C11	0.0318 (19)	0.038 (2)	0.042 (2)	0.0017 (17)	−0.0023 (16)	0.0104 (18)
C12	0.038 (2)	0.045 (3)	0.039 (2)	−0.0061 (19)	−0.0050 (17)	0.0008 (19)
C13	0.047 (2)	0.039 (2)	0.038 (2)	−0.0066 (19)	−0.0014 (18)	0.0015 (19)

Geometric parameters (Å, º) top

F1—C1	1.334 (6)	C4—C5	1.521 (6)
F2—C1	1.298 (5)	C4—H4A	0.9800
F3—C1	1.348 (6)	C5—C6	1.525 (6)
O1—C2	1.210 (5)	C5—H5A	0.9700
O2—N2	1.211 (5)	C5—H5B	0.9700
O3—N2	1.221 (5)	C6—C13	1.523 (6)
O4—N3	1.227 (5)	C6—C7	1.535 (6)
O5—N3	1.236 (5)	C6—H6A	0.9800
N1—C2	1.325 (6)	C7—H7A	0.9700
N1—C3	1.482 (5)	C7—H7B	0.9700
N1—C7	1.483 (5)	C8—C9	1.379 (6)
N2—C10	1.470 (5)	C8—C13	1.385 (5)
N3—C11	1.427 (5)	C9—C10	1.370 (5)
C1—C2	1.530 (6)	C9—H9A	0.9300
C3—C4	1.516 (6)	C10—C11	1.403 (5)
C3—H3A	0.9700	C11—C12	1.407 (6)
C3—H3B	0.9700	C12—C13	1.349 (6)
C4—C8	1.519 (5)	C12—H12A	0.9300

C2—N1—C3	114.0 (3)	C4—C5—H5B	111.7
C2—N1—C7	123.4 (3)	C6—C5—H5B	111.7
C3—N1—C7	121.4 (4)	H5A—C5—H5B	109.5
O2—N2—O3	124.6 (4)	C13—C6—C5	100.5 (3)
O2—N2—C10	117.6 (4)	C13—C6—C7	112.1 (4)
O3—N2—C10	117.8 (4)	C5—C6—C7	109.1 (4)
O4—N3—O5	122.9 (4)	C13—C6—H6A	111.5
O4—N3—C11	118.3 (4)	C5—C6—H6A	111.5
O5—N3—C11	118.8 (4)	C7—C6—H6A	111.5
F2—C1—F1	107.7 (4)	N1—C7—C6	111.6 (3)
F2—C1—F3	106.5 (4)	N1—C7—H7A	109.3
F1—C1—F3	105.6 (4)	C6—C7—H7A	109.3
F2—C1—C2	114.8 (4)	N1—C7—H7B	109.3
F1—C1—C2	110.0 (4)	C6—C7—H7B	109.3
F3—C1—C2	111.8 (4)	H7A—C7—H7B	108.0
O1—C2—N1	124.6 (4)	C9—C8—C13	120.4 (4)
O1—C2—C1	117.3 (4)	C9—C8—C4	130.6 (4)
N1—C2—C1	118.1 (4)	C13—C8—C4	109.1 (4)
N1—C3—C4	112.7 (3)	C10—C9—C8	118.4 (3)
N1—C3—H3A	109.0	C10—C9—H9A	120.8
C4—C3—H3A	109.0	C8—C9—H9A	120.8
N1—C3—H3B	109.0	C9—C10—C11	121.5 (4)
C4—C3—H3B	109.0	C9—C10—N2	116.7 (3)
H3A—C3—H3B	107.8	C11—C10—N2	121.6 (4)
C3—C4—C8	110.0 (4)	C10—C11—C12	119.0 (4)
C3—C4—C5	110.6 (3)	C10—C11—N3	121.9 (4)
C8—C4—C5	100.0 (3)	C12—C11—N3	119.0 (4)
C3—C4—H4A	111.9	C13—C12—C11	118.4 (4)
C8—C4—H4A	111.9	C13—C12—H12A	120.8
C5—C4—H4A	111.9	C11—C12—H12A	120.8
C4—C5—C6	100.3 (4)	C12—C13—C8	122.2 (4)
C4—C5—H5A	111.7	C12—C13—C6	130.3 (4)
C6—C5—H5A	111.7	C8—C13—C6	107.5 (4)

C3—N1—C2—O1	−1.8 (6)	C4—C8—C9—C10	−177.4 (4)
C7—N1—C2—O1	−169.0 (4)	C8—C9—C10—C11	−1.7 (6)
C3—N1—C2—C1	178.8 (4)	C8—C9—C10—N2	172.3 (4)
C7—N1—C2—C1	11.6 (6)	O2—N2—C10—C9	63.6 (5)
F2—C1—C2—O1	−121.0 (5)	O3—N2—C10—C9	−114.5 (5)
F1—C1—C2—O1	0.6 (6)	O2—N2—C10—C11	−122.3 (5)
F3—C1—C2—O1	117.5 (5)	O3—N2—C10—C11	59.5 (6)
F2—C1—C2—N1	58.5 (6)	C9—C10—C11—C12	0.1 (6)
F1—C1—C2—N1	−179.9 (4)	N2—C10—C11—C12	−173.6 (4)
F3—C1—C2—N1	−63.0 (5)	C9—C10—C11—N3	−177.6 (4)
C2—N1—C3—C4	168.3 (4)	N2—C10—C11—N3	8.7 (6)
C7—N1—C3—C4	−24.2 (5)	O4—N3—C11—C10	−154.4 (4)
N1—C3—C4—C8	−61.6 (5)	O5—N3—C11—C10	25.1 (6)
N1—C3—C4—C5	48.0 (5)	O4—N3—C11—C12	28.0 (6)
C3—C4—C5—C6	−71.8 (4)	O5—N3—C11—C12	−152.6 (4)
C8—C4—C5—C6	44.2 (4)	C10—C11—C12—C13	2.4 (6)
C4—C5—C6—C13	−44.6 (4)	N3—C11—C12—C13	−179.8 (4)
C4—C5—C6—C7	73.4 (4)	C11—C12—C13—C8	−3.4 (6)
C2—N1—C7—C6	−167.6 (4)	C11—C12—C13—C6	177.3 (4)
C3—N1—C7—C6	26.0 (5)	C9—C8—C13—C12	1.8 (7)
C13—C6—C7—N1	58.8 (5)	C4—C8—C13—C12	−179.6 (4)
C5—C6—C7—N1	−51.7 (5)	C9—C8—C13—C6	−178.8 (4)
C3—C4—C8—C9	−93.2 (5)	C4—C8—C13—C6	−0.2 (5)
C5—C4—C8—C9	150.4 (5)	C5—C6—C13—C12	−152.3 (5)
C3—C4—C8—C13	88.4 (4)	C7—C6—C13—C12	91.9 (5)
C5—C4—C8—C13	−28.0 (4)	C5—C6—C13—C8	28.3 (5)
C13—C8—C9—C10	0.8 (6)	C7—C6—C13—C8	−87.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···F2	0.97	2.34	3.002 (6)	124
C9—H9A···O1ⁱ	0.93	2.41	3.338 (5)	173

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀F₃N₃O₅
M_r	345.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	9.6400 (19), 7.7430 (15), 18.687 (4)
β (°)	96.98 (3)
V (Å³)	1384.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.955, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	2673, 2513, 1592
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.183, 1.02
No. of reflections	2513
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.35

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···F2	0.97	2.34	3.002 (6)	124.00
C9—H9A···O1ⁱ	0.93	2.41	3.338 (5)	173.00

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank the Center for Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2425

doi:10.1107/S1600536808028158

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(4,5-Di­nitro-10-aza­tri­cyclo­[6.3.1.02,7]dodeca-2,4,6-trien-10-yl)-2,2,2-tri­fluoro­ethanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(4,5-Dinitro-10-azatricyclo[6.3.1.0^2,7]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoroethanone