2,4,6-Tri-nitro-phenyl furan-2-carboxyl-ate.

In the title carboxyl-ate derivative, C11H5N3O9, the picryl ring forms an angle of 75.79 (7)° with the ester fragment, indicating a near perpendicular disposition. The nitro substituents are variously oriented with respect to the picryl ring [dihedral angles = 3.22 (10), 16.03 (12) and 36.63 (10)°]. In the crystal, mol-ecules form helical chains sustained by C-H⋯O inter-actions along [010]. The furanyl residue is disordered, having two coplanar slightly displaced orientations [major component = 0.730 (9)].

Related literature

For similar esters, see: Moreno-Fuquen et al. (2012 ▶, 2013 ▶). For hydrogen bonding, see: Nardelli (1995 ▶).

Experimental

Crystal data

C11H5N3O9

M = 323.18

Orthorhombic,

a = 7.0982 (3) Å

b = 8.4931 (4) Å

c = 20.4970 (9) Å

V = 1235.68 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 123 K

0.35 × 0.22 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

4861 measured reflections

2669 independent reflections

2395 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.095

S = 1.06

2669 reflections

224 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813028274/tk5263sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028274/tk5263Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028274/tk5263Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H5N3O9	Dx = 1.737 Mg m−3
Mr = 323.18	Melting point: 435(1) K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4861 reflections
a = 7.0982 (3) Å	θ = 3.0–27.0°
b = 8.4931 (4) Å	µ = 0.16 mm−1
c = 20.4970 (9) Å	T = 123 K
V = 1235.68 (10) Å3	Block, pale-yellow
Z = 4	0.35 × 0.22 × 0.11 mm
F(000) = 656

Oxford Diffraction Xcalibur E diffractometer	2395 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 27.0°, θmin = 3.0°
ω scans	h = −9→9
4861 measured reflections	k = −10→8
2669 independent reflections	l = −26→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.1241P] where P = (Fo2 + 2Fc2)/3
2669 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.27 e Å−3
12 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.18433 (19)	0.8534 (2)	0.26898 (7)	0.0305 (4)
O2	−0.1529 (2)	0.8749 (2)	0.37311 (8)	0.0363 (5)
O3	0.4160 (2)	0.7394 (3)	0.48267 (7)	0.0428 (5)
O4	0.6111 (2)	0.5845 (2)	0.43352 (8)	0.0375 (4)
O5	0.5765 (2)	0.53627 (19)	0.19586 (8)	0.0293 (4)
O6	0.4404 (2)	0.7359 (2)	0.15032 (7)	0.0401 (5)
O7	0.08707 (19)	0.73046 (16)	0.19797 (6)	0.0204 (3)
O8	0.11722 (19)	0.99352 (16)	0.18492 (7)	0.0215 (3)
N1	−0.0930 (2)	0.8411 (2)	0.31894 (8)	0.0215 (4)
N2	0.4759 (2)	0.6722 (2)	0.43417 (8)	0.0253 (4)
N3	0.4676 (2)	0.6478 (2)	0.19627 (8)	0.0225 (4)
C1	0.1840 (3)	0.7368 (2)	0.25609 (9)	0.0164 (4)
C2	0.1026 (3)	0.7816 (2)	0.31521 (9)	0.0178 (4)
C3	0.1979 (3)	0.7648 (3)	0.37363 (10)	0.0194 (4)
H3	0.1425	0.7973	0.4136	0.023*
C4	0.3760 (3)	0.6994 (2)	0.37219 (9)	0.0199 (4)
C5	0.4643 (3)	0.6543 (2)	0.31504 (9)	0.0188 (4)
H5	0.5859	0.6077	0.3153	0.023*
C6	0.3678 (3)	0.6802 (2)	0.25754 (9)	0.0182 (4)
C7	0.0627 (3)	0.8691 (2)	0.16480 (9)	0.0169 (4)
C8A	−0.032 (7)	0.8401 (19)	0.1031 (12)	0.020 (2)	0.730 (9)
O9A	−0.0526 (9)	0.9683 (6)	0.0630 (3)	0.0319 (8)	0.730 (9)
C9A	−0.1062 (9)	0.7071 (7)	0.0776 (2)	0.0194 (10)	0.730 (9)
H9	−0.1115	0.6058	0.0972	0.023*	0.730 (9)
C10A	−0.1754 (5)	0.7519 (7)	0.0143 (2)	0.0298 (12)	0.730 (9)
H10	−0.2333	0.6848	−0.0169	0.036*	0.730 (9)
C11A	−0.1425 (7)	0.9074 (7)	0.0077 (2)	0.0316 (11)	0.730 (9)
H11	−0.1758	0.9678	−0.0296	0.038*	0.730 (9)
C8B	−0.044 (19)	0.835 (5)	0.105 (3)	0.020 (2)	0.270 (9)
O9B	−0.077 (3)	0.9350 (19)	0.0532 (8)	0.0319 (8)	0.270 (9)
C9B	−0.103 (3)	0.687 (2)	0.0960 (7)	0.0194 (10)	0.270 (9)
H9B	−0.0902	0.5978	0.1238	0.023*	0.270 (9)
C10B	−0.1880 (18)	0.6968 (18)	0.0363 (6)	0.0298 (12)	0.270 (9)
H10B	−0.2524	0.6115	0.0163	0.036*	0.270 (9)
C11B	−0.171 (2)	0.840 (2)	0.0088 (7)	0.0316 (11)	0.270 (9)
H11B	−0.2151	0.8698	−0.0332	0.038*	0.270 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0175 (7)	0.0428 (11)	0.0313 (8)	0.0018 (8)	−0.0020 (6)	0.0103 (8)
O2	0.0285 (8)	0.0485 (12)	0.0320 (9)	0.0119 (8)	0.0068 (7)	−0.0089 (9)
O3	0.0451 (10)	0.0646 (13)	0.0187 (8)	0.0105 (11)	−0.0038 (7)	−0.0073 (9)
O4	0.0357 (9)	0.0426 (11)	0.0341 (9)	0.0117 (9)	−0.0114 (8)	0.0043 (8)
O5	0.0273 (7)	0.0241 (8)	0.0364 (9)	0.0105 (7)	0.0031 (7)	−0.0032 (7)
O6	0.0455 (10)	0.0491 (11)	0.0256 (8)	0.0213 (10)	0.0083 (7)	0.0133 (9)
O7	0.0236 (7)	0.0165 (7)	0.0212 (7)	0.0004 (6)	−0.0081 (6)	−0.0001 (6)
O8	0.0218 (7)	0.0184 (8)	0.0243 (8)	−0.0004 (6)	−0.0002 (7)	−0.0004 (7)
N1	0.0178 (8)	0.0186 (8)	0.0280 (9)	−0.0005 (7)	0.0033 (7)	0.0012 (9)
N2	0.0263 (10)	0.0300 (11)	0.0196 (9)	−0.0045 (8)	−0.0051 (7)	0.0023 (9)
N3	0.0205 (8)	0.0255 (10)	0.0215 (9)	0.0041 (8)	−0.0007 (7)	−0.0002 (8)
C1	0.0185 (9)	0.0115 (10)	0.0191 (9)	−0.0028 (8)	−0.0032 (8)	0.0023 (8)
C2	0.0148 (8)	0.0128 (9)	0.0257 (10)	−0.0009 (7)	0.0016 (8)	0.0030 (8)
C3	0.0214 (10)	0.0171 (10)	0.0198 (9)	−0.0040 (8)	0.0033 (8)	−0.0019 (9)
C4	0.0209 (9)	0.0180 (11)	0.0208 (10)	−0.0039 (8)	−0.0048 (8)	0.0027 (8)
C5	0.0158 (8)	0.0159 (9)	0.0247 (10)	−0.0013 (7)	−0.0035 (8)	0.0022 (10)
C6	0.0192 (9)	0.0154 (10)	0.0200 (10)	−0.0006 (8)	0.0018 (8)	0.0010 (8)
C7	0.0127 (8)	0.0189 (11)	0.0191 (9)	0.0027 (8)	0.0016 (7)	0.0009 (8)
C8A	0.017 (6)	0.0232 (14)	0.0196 (17)	0.0038 (12)	0.002 (3)	0.0022 (11)
O9A	0.039 (2)	0.032 (3)	0.025 (2)	0.0024 (17)	−0.0090 (14)	−0.0029 (16)
C9A	0.0214 (10)	0.018 (2)	0.018 (3)	0.0009 (13)	−0.009 (2)	−0.004 (2)
C10A	0.0299 (14)	0.036 (3)	0.023 (3)	0.002 (2)	−0.0067 (18)	−0.005 (2)
C11A	0.034 (2)	0.042 (3)	0.0184 (14)	0.006 (2)	−0.0097 (13)	−0.001 (2)
C8B	0.017 (6)	0.0232 (14)	0.0196 (17)	0.0038 (12)	0.002 (3)	0.0022 (11)
O9B	0.039 (2)	0.032 (3)	0.025 (2)	0.0024 (17)	−0.0090 (14)	−0.0029 (16)
C9B	0.0214 (10)	0.018 (2)	0.018 (3)	0.0009 (13)	−0.009 (2)	−0.004 (2)
C10B	0.0299 (14)	0.036 (3)	0.023 (3)	0.002 (2)	−0.0067 (18)	−0.005 (2)
C11B	0.034 (2)	0.042 (3)	0.0184 (14)	0.006 (2)	−0.0097 (13)	−0.001 (2)

O1—N1	1.216 (2)	C5—H5	0.9500
O2—N1	1.223 (2)	C7—C8A	1.453 (7)
O3—N2	1.223 (2)	C7—C8B	1.471 (17)
O4—N2	1.215 (2)	C8A—C9A	1.352 (7)
O5—N3	1.223 (2)	C8A—O9A	1.372 (6)
O6—N3	1.218 (2)	O9A—C11A	1.400 (5)
O7—C7	1.371 (2)	C9A—C10A	1.439 (5)
O7—C1	1.377 (2)	C9A—H9	0.9500
O8—C7	1.198 (2)	C10A—C11A	1.348 (5)
N1—C2	1.479 (2)	C10A—H10	0.9500
N2—C4	1.473 (2)	C11A—H11	0.9500
N3—C6	1.468 (2)	C8B—C9B	1.345 (18)
C1—C6	1.391 (3)	C8B—O9B	1.376 (10)
C1—C2	1.395 (3)	O9B—C11B	1.388 (9)
C2—C3	1.383 (3)	C9B—C10B	1.365 (12)
C3—C4	1.381 (3)	C9B—H9B	0.9500
C3—H3	0.9500	C10B—C11B	1.344 (13)
C4—C5	1.383 (3)	C10B—H10B	0.9500
C5—C6	1.381 (3)	C11B—H11B	0.9500
C7—O7—C1	117.29 (15)	O7—C7—C8A	110.1 (4)
O1—N1—O2	123.95 (16)	O8—C7—C8B	128.7 (12)
O1—N1—C2	119.09 (16)	O7—C7—C8B	108.1 (10)
O2—N1—C2	116.96 (16)	C9A—C8A—O9A	113.0 (5)
O4—N2—O3	124.75 (18)	C9A—C8A—C7	131.2 (6)
O4—N2—C4	117.84 (17)	O9A—C8A—C7	115.8 (6)
O3—N2—C4	117.40 (18)	C8A—O9A—C11A	103.9 (5)
O6—N3—O5	124.81 (17)	C8A—C9A—C10A	105.1 (4)
O6—N3—C6	118.03 (17)	C8A—C9A—H9	127.5
O5—N3—C6	117.13 (17)	C10A—C9A—H9	127.5
O7—C1—C6	118.28 (17)	C11A—C10A—C9A	106.9 (4)
O7—C1—C2	123.73 (17)	C11A—C10A—H10	126.6
C6—C1—C2	117.64 (17)	C9A—C10A—H10	126.6
C3—C2—C1	121.45 (17)	C10A—C11A—O9A	111.1 (4)
C3—C2—N1	116.71 (17)	C10A—C11A—H11	124.5
C1—C2—N1	121.77 (17)	O9A—C11A—H11	124.5
C4—C3—C2	118.07 (18)	C9B—C8B—O9B	114.8 (15)
C4—C3—H3	121.0	C9B—C8B—C7	117.3 (16)
C2—C3—H3	121.0	O9B—C8B—C7	127.7 (18)
C3—C4—C5	123.00 (18)	C8B—O9B—C11B	103.2 (13)
C3—C4—N2	119.04 (18)	C8B—C9B—C10B	101.5 (13)
C5—C4—N2	117.95 (17)	C8B—C9B—H9B	129.3
C6—C5—C4	117.01 (16)	C10B—C9B—H9B	129.3
C6—C5—H5	121.5	C11B—C10B—C9B	113.3 (13)
C4—C5—H5	121.5	C11B—C10B—H10B	123.4
C5—C6—C1	122.59 (18)	C9B—C10B—H10B	123.4
C5—C6—N3	117.46 (16)	C10B—C11B—O9B	107.1 (13)
C1—C6—N3	119.95 (17)	C10B—C11B—H11B	126.5
O8—C7—O7	123.08 (17)	O9B—C11B—H11B	126.5
O8—C7—C8A	126.8 (4)
C7—O7—C1—C6	−105.5 (2)	C1—O7—C7—O8	−1.9 (3)
C7—O7—C1—C2	81.4 (2)	C1—O7—C7—C8A	177 (2)
O7—C1—C2—C3	170.67 (19)	C1—O7—C7—C8B	−180 (6)
C6—C1—C2—C3	−2.5 (3)	O8—C7—C8A—C9A	−176 (3)
O7—C1—C2—N1	−6.0 (3)	O7—C7—C8A—C9A	5 (6)
C6—C1—C2—N1	−179.10 (17)	C8B—C7—C8A—C9A	−55 (71)
O1—N1—C2—C3	−177.87 (19)	O8—C7—C8A—O9A	3 (5)
O2—N1—C2—C3	2.0 (3)	O7—C7—C8A—O9A	−175 (3)
O1—N1—C2—C1	−1.1 (3)	C8B—C7—C8A—O9A	125 (80)
O2—N1—C2—C1	178.8 (2)	C9A—C8A—O9A—C11A	−2 (4)
C1—C2—C3—C4	−1.2 (3)	C7—C8A—O9A—C11A	179 (3)
N1—C2—C3—C4	175.64 (18)	O9A—C8A—C9A—C10A	2 (4)
C2—C3—C4—C5	1.8 (3)	C7—C8A—C9A—C10A	−178 (4)
C2—C3—C4—N2	−176.63 (19)	C8A—C9A—C10A—C11A	−2 (3)
O4—N2—C4—C3	164.0 (2)	C9A—C10A—C11A—O9A	0.8 (6)
O3—N2—C4—C3	−15.7 (3)	C8A—O9A—C11A—C10A	0 (2)
O4—N2—C4—C5	−14.5 (3)	O8—C7—C8B—C9B	−174 (6)
O3—N2—C4—C5	165.8 (2)	O7—C7—C8B—C9B	4 (13)
C3—C4—C5—C6	1.3 (3)	C8A—C7—C8B—C9B	125 (87)
N2—C4—C5—C6	179.71 (18)	O8—C7—C8B—O9B	12 (18)
C4—C5—C6—C1	−5.2 (3)	O7—C7—C8B—O9B	−170 (11)
C4—C5—C6—N3	173.92 (19)	C8A—C7—C8B—O9B	−49 (64)
O7—C1—C6—C5	−167.74 (19)	C9B—C8B—O9B—C11B	2 (12)
C2—C1—C6—C5	5.8 (3)	C7—C8B—O9B—C11B	176 (11)
O7—C1—C6—N3	13.2 (3)	O9B—C8B—C9B—C10B	−3 (12)
C2—C1—C6—N3	−173.29 (18)	C7—C8B—C9B—C10B	−178 (9)
O6—N3—C6—C5	−142.3 (2)	C8B—C9B—C10B—C11B	4 (7)
O5—N3—C6—C5	35.7 (3)	C9B—C10B—C11B—O9B	−3 (2)
O6—N3—C6—C1	36.8 (3)	C8B—O9B—C11B—C10B	1 (7)
O5—N3—C6—C1	−145.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O8i	0.95	2.32	3.270 (2)	180

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O8i	0.95	2.32	3.270 (2)	180

Symmetry code: (i) .