6,6′-Dimeth­oxy-2,2′,3,3′,5-penta­nitro-1,1′-biphen­yl

Jiang, Y.-Y.; Miao, S.-B.; Deng, D.-S.; Ji, B.-M.

doi:10.1107/S1600536808011926

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o951

doi:10.1107/S1600536808011926

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6,6′-Dimethoxy-2,2′,3,3′,5-pentanitro-1,1′-biphenyl

Yuan-Yuan Jiang,^a Shao-Bin Miao,^b Dong-Sheng Deng ^b and Bao-Ming Ji ^b ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
^*Correspondence e-mail: lyhxxjbm@126.com

(Received 8 April 2008; accepted 24 April 2008; online 3 May 2008)

In the axially chiral title compound, C₁₄H₉N₅O₁₂, the dihedral angle between the two benzene rings is 86.0 (8)°. In the crystal structure, the molecules display a two-dimensional framework formed by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Chen et al. (2001 ); Fischer et al. (2007 ); Narayanan et al. (2005 ); Saito & Koizumi (2005 ); Xiao et al. (2007 ); Yang et al. (2005 ).

Experimental

Crystal data

C₁₄H₉N₅O₁₂
M_r = 439.26
Triclinic, $[P \overline 1]$
a = 10.3765 (13) Å
b = 10.4423 (13) Å
c = 10.4429 (13) Å
α = 82.5650 (10)°
β = 62.2850 (10)°
γ = 60.5200 (10)°
V = 864.73 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 291 (2) K
0.41 × 0.34 × 0.29 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.940, T_max = 0.958
6598 measured reflections
3194 independent reflections
2686 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.117
S = 1.02
3194 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O3	0.96	2.45	2.926 (3)	111
C14—H14B⋯O10ⁱ	0.96	2.55	3.502 (3)	174
C14—H14C⋯O8ⁱⁱ	0.96	2.58	3.371 (3)	140
Symmetry codes: (i) x+1, y-1, z; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011926/si2086sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011926/si2086Isup2.hkl

checkCIF report

Comment top

Nitro compounds, specially aromatic nitro compounds have been widely studied owing to their potential application in, for example, pathology (Narayanan, et al., 2005), materials science (Saito & Koizumi, 2005). On the other hand, in our search for chiral compounds, the title related chiral 6,6'-dimethoxy-2,3,2',5'-tetranitro-1,1'-biphenyl compound was synthesized by Xiao et al., (2007). Herein, as an extension to our previous investigation, we report the synthesis and structural characterization of the title compound.

In contrast to our highly substituted biphenyl compounds, the unsubstituted biphenyl groups in compounds synthesized by Fischer et al., (2007) were found to be approximately planar. The molecular geometry in the title compound displays special behavior, the dihedral angle between the benzene rings is 94.0 (8)°, and all the nitro groups at positions 2,3,5,2',3' are twisted out of the corresponding rings which is 45.5 (3)°, 13.5 (5)°, 98.4 (3)°, 6.6 (4)° and 83.5 (5)°, respectively, as depicted in Fig.1. Bond lengths and angles are in good agreement with the dinitrophenyl group in the structure of 1-(2,4-dinitrophenyl)azo-1-nitrocyclohexane, reported by Yang et al., (2005). One intramolecular C—H···O hydrogen bond is observed in the title molecule, and the two intermolecular C—H···O hydrogen bonding contacts (Table 1) form closed two-dimensional grid motifs (Fig. 2).

Related literature top

For related literature, see: Chen et al. (2001); Fischer et al. (2007); Narayanan et al. (2005); Saito & Koizumi (2005); Xiao et al. (2007); Yang et al. (2005).

Experimental top

All chemicals and solvents purchased were of reagent grade and used without further purification. The precursor 6,6'-Dimethoxy-2,2'-dinitro-1,1'-biphenyl was prepared according to the reported procedure (Chen et al., 2001). However, the title compound was obtained by chance when we tried to prepare the 6,6'-Dimethoxy-2,3,5,2',3',5'-hexanitro-1,1'-biphenyl compound. That is, the title compound was synthesized by the nitration reaction of the precursor (0.5 mmol) in 10 ml of concentrated nitric acid at room temperature for 24 h. The resulting solution was poured into 30 ml of ice water and the resulting precipitate was collected by filtration and recrystallized from ethyl acetate to obtain the title crystals, which were suitable for X-ray diffraction analysis. Cautious, the title compound has potential explosive property.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Atom numbering scheme for the title compound with 30% probability displacement ellipsoids.
	Fig. 2. View of the two-dimensional sheet structure. (C—H···O interactions are represented as broken lines).

6,6'-Dimethoxy-2,2',3,3',5-pentanitro-1,1'-biphenyl top

Crystal data top

C₁₄H₉N₅O₁₂	Z = 2
M_r = 439.26	F(000) = 448
Triclinic, P1	D_x = 1.687 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3765 (13) Å	Cell parameters from 2971 reflections
b = 10.4423 (13) Å	θ = 2.4–25.5°
c = 10.4429 (13) Å	µ = 0.15 mm⁻¹
α = 82.565 (1)°	T = 291 K
β = 62.285 (1)°	Block, yellow
γ = 60.520 (1)°	0.41 × 0.34 × 0.29 mm
V = 864.73 (19) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3194 independent reflections
Radiation source: fine-focus sealed tube	2686 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.940, T_max = 0.958	k = −12→12
6598 measured reflections	l = −12→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.059P)² + 0.3851P] where P = (F_o² + 2F_c²)/3
3194 reflections	(Δ/σ)_max < 0.001
282 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₉N₅O₁₂	γ = 60.520 (1)°
M_r = 439.26	V = 864.73 (19) Å³
Triclinic, P1	Z = 2
a = 10.3765 (13) Å	Mo Kα radiation
b = 10.4423 (13) Å	µ = 0.15 mm⁻¹
c = 10.4429 (13) Å	T = 291 K
α = 82.565 (1)°	0.41 × 0.34 × 0.29 mm
β = 62.285 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3194 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2686 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.958	R_int = 0.013
6598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
3194 reflections	Δρ_min = −0.22 e Å⁻³
282 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	0.36354 (18)	0.70656 (16)	0.19497 (14)	0.0448 (3)
O2	0.69388 (15)	0.72440 (14)	0.24022 (14)	0.0382 (3)
O3	0.4217 (2)	0.40331 (19)	0.2500 (2)	0.0678 (5)
O4	0.1905 (2)	0.4489 (2)	0.4428 (3)	0.0852 (6)
O5	0.2186 (3)	0.6187 (2)	0.84423 (19)	0.0803 (6)
O6	0.2172 (2)	0.8273 (2)	0.83302 (16)	0.0648 (5)
O7	0.5003 (2)	0.8533 (2)	0.57692 (17)	0.0582 (4)
O8	0.2549 (2)	1.03379 (17)	0.61824 (19)	0.0640 (5)
O9	0.2989 (2)	1.33902 (17)	0.06894 (18)	0.0571 (4)
O10	0.0962 (2)	1.3106 (2)	0.2303 (2)	0.0846 (7)
O11	0.0882 (2)	1.0384 (2)	0.2635 (2)	0.0761 (6)
O12	0.04620 (19)	1.1239 (2)	0.46358 (18)	0.0702 (5)
N1	0.3036 (2)	0.4748 (2)	0.3675 (2)	0.0507 (5)
N2	0.2378 (2)	0.7181 (2)	0.77767 (18)	0.0484 (4)
N3	0.3645 (2)	0.90493 (19)	0.58132 (16)	0.0404 (4)
N4	0.2444 (2)	1.26902 (17)	0.15879 (17)	0.0391 (4)
N5	0.1327 (2)	1.06936 (18)	0.3386 (2)	0.0433 (4)
C1	0.3442 (2)	0.69672 (19)	0.33107 (19)	0.0316 (4)
C2	0.3056 (2)	0.59612 (19)	0.4225 (2)	0.0351 (4)
C3	0.2736 (2)	0.6019 (2)	0.5661 (2)	0.0371 (4)
H3	0.2441	0.5362	0.6249	0.045*
C4	0.2859 (2)	0.7060 (2)	0.62141 (19)	0.0351 (4)
C5	0.3359 (2)	0.80022 (19)	0.52985 (19)	0.0314 (4)
C6	0.3661 (2)	0.79704 (18)	0.38642 (18)	0.0283 (4)
C7	0.4211 (2)	0.89880 (18)	0.28967 (17)	0.0280 (4)
C8	0.5928 (2)	0.85656 (18)	0.21610 (18)	0.0287 (4)
C9	0.6454 (2)	0.9505 (2)	0.12600 (18)	0.0330 (4)
H9	0.7584	0.9224	0.0769	0.040*
C10	0.5303 (2)	1.08464 (19)	0.10979 (18)	0.0331 (4)
H10	0.5660	1.1471	0.0507	0.040*
C11	0.3623 (2)	1.12714 (18)	0.18047 (18)	0.0308 (4)
C12	0.3096 (2)	1.03275 (19)	0.26904 (18)	0.0302 (4)
C13	0.2548 (4)	0.6888 (3)	0.1570 (3)	0.0651 (7)
H13A	0.3124	0.5908	0.1070	0.098*
H13B	0.2243	0.7609	0.0946	0.098*
H13C	0.1559	0.7028	0.2442	0.098*
C14	0.8715 (2)	0.6715 (2)	0.1654 (3)	0.0536 (6)
H14A	0.9102	0.6645	0.0619	0.080*
H14B	0.9285	0.5755	0.1910	0.080*
H14C	0.8939	0.7394	0.1934	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0591 (9)	0.0572 (9)	0.0359 (7)	−0.0397 (8)	−0.0238 (7)	0.0089 (6)
O2	0.0289 (6)	0.0334 (7)	0.0451 (7)	−0.0130 (5)	−0.0157 (6)	0.0099 (5)
O3	0.0824 (13)	0.0479 (9)	0.0718 (12)	−0.0313 (9)	−0.0322 (10)	−0.0061 (8)
O4	0.0745 (13)	0.0756 (13)	0.1234 (17)	−0.0582 (11)	−0.0347 (12)	0.0068 (12)
O5	0.1272 (17)	0.1048 (15)	0.0559 (10)	−0.0899 (15)	−0.0508 (11)	0.0482 (10)
O6	0.0882 (13)	0.0741 (12)	0.0384 (8)	−0.0475 (10)	−0.0264 (8)	0.0091 (8)
O7	0.0600 (10)	0.0829 (12)	0.0526 (9)	−0.0446 (9)	−0.0309 (8)	0.0070 (8)
O8	0.0900 (13)	0.0396 (9)	0.0696 (11)	−0.0276 (9)	−0.0460 (10)	0.0029 (7)
O9	0.0681 (10)	0.0444 (8)	0.0624 (10)	−0.0317 (8)	−0.0342 (8)	0.0286 (7)
O10	0.0399 (9)	0.0592 (11)	0.1113 (16)	−0.0129 (8)	−0.0246 (10)	0.0458 (11)
O11	0.0482 (10)	0.0769 (12)	0.1132 (16)	−0.0263 (9)	−0.0453 (10)	−0.0055 (11)
O12	0.0383 (8)	0.0812 (12)	0.0476 (10)	−0.0124 (8)	−0.0077 (7)	0.0123 (9)
N1	0.0541 (11)	0.0396 (9)	0.0703 (13)	−0.0277 (9)	−0.0332 (10)	0.0094 (9)
N2	0.0543 (11)	0.0646 (12)	0.0385 (9)	−0.0381 (10)	−0.0243 (8)	0.0213 (9)
N3	0.0540 (10)	0.0481 (10)	0.0313 (8)	−0.0321 (9)	−0.0224 (7)	0.0098 (7)
N4	0.0467 (10)	0.0305 (8)	0.0402 (9)	−0.0181 (7)	−0.0226 (8)	0.0103 (7)
N5	0.0327 (8)	0.0344 (9)	0.0536 (11)	−0.0137 (7)	−0.0189 (8)	0.0149 (7)
C1	0.0280 (8)	0.0314 (9)	0.0333 (9)	−0.0139 (7)	−0.0132 (7)	0.0033 (7)
C2	0.0309 (9)	0.0296 (9)	0.0464 (10)	−0.0163 (7)	−0.0173 (8)	0.0042 (8)
C3	0.0335 (9)	0.0347 (10)	0.0450 (11)	−0.0203 (8)	−0.0185 (8)	0.0158 (8)
C4	0.0338 (9)	0.0400 (10)	0.0328 (9)	−0.0198 (8)	−0.0162 (8)	0.0116 (8)
C5	0.0305 (9)	0.0312 (9)	0.0340 (9)	−0.0153 (7)	−0.0166 (7)	0.0064 (7)
C6	0.0247 (8)	0.0257 (8)	0.0322 (9)	−0.0112 (7)	−0.0132 (7)	0.0055 (7)
C7	0.0317 (9)	0.0279 (8)	0.0263 (8)	−0.0158 (7)	−0.0136 (7)	0.0036 (6)
C8	0.0308 (9)	0.0288 (8)	0.0281 (8)	−0.0143 (7)	−0.0147 (7)	0.0022 (7)
C9	0.0314 (9)	0.0375 (9)	0.0306 (9)	−0.0202 (8)	−0.0109 (7)	0.0026 (7)
C10	0.0427 (10)	0.0336 (9)	0.0288 (9)	−0.0250 (8)	−0.0146 (8)	0.0060 (7)
C11	0.0383 (9)	0.0271 (8)	0.0288 (8)	−0.0156 (7)	−0.0177 (7)	0.0048 (7)
C12	0.0303 (9)	0.0311 (9)	0.0281 (8)	−0.0153 (7)	−0.0127 (7)	0.0037 (7)
C13	0.098 (2)	0.0792 (18)	0.0680 (15)	−0.0620 (16)	−0.0593 (15)	0.0260 (13)
C14	0.0295 (10)	0.0445 (12)	0.0705 (15)	−0.0120 (9)	−0.0182 (10)	0.0085 (10)

Geometric parameters (Å, º) top

O1—C1	1.337 (2)	C2—C3	1.380 (3)
O1—C13	1.451 (3)	C3—C4	1.379 (3)
O2—C8	1.341 (2)	C3—H3	0.9300
O2—C14	1.443 (2)	C4—C5	1.396 (2)
O3—N1	1.225 (3)	C5—C6	1.382 (2)
O4—N1	1.211 (2)	C6—C7	1.503 (2)
O5—N2	1.220 (2)	C7—C12	1.379 (2)
O6—N2	1.223 (2)	C7—C8	1.414 (2)
O7—N3	1.215 (2)	C8—C9	1.399 (2)
O8—N3	1.214 (2)	C9—C10	1.377 (3)
O9—N4	1.212 (2)	C9—H9	0.9300
O10—N4	1.212 (2)	C10—C11	1.381 (3)
O11—N5	1.218 (2)	C10—H10	0.9300
O12—N5	1.197 (2)	C11—C12	1.396 (2)
N1—C2	1.470 (2)	C13—H13A	0.9600
N2—C4	1.470 (2)	C13—H13B	0.9600
N3—C5	1.481 (2)	C13—H13C	0.9600
N4—C11	1.459 (2)	C14—H14A	0.9600
N5—C12	1.478 (2)	C14—H14B	0.9600
C1—C2	1.405 (2)	C14—H14C	0.9600
C1—C6	1.413 (2)

C1—O1—C13	120.36 (16)	C5—C6—C7	120.87 (15)
C8—O2—C14	118.30 (14)	C1—C6—C7	119.98 (15)
O4—N1—O3	124.87 (19)	C12—C7—C8	118.36 (15)
O4—N1—C2	118.4 (2)	C12—C7—C6	122.25 (15)
O3—N1—C2	116.66 (17)	C8—C7—C6	119.39 (14)
O5—N2—O6	124.23 (18)	O2—C8—C9	125.08 (15)
O5—N2—C4	117.39 (18)	O2—C8—C7	115.04 (14)
O6—N2—C4	118.38 (16)	C9—C8—C7	119.88 (15)
O8—N3—O7	126.09 (18)	C10—C9—C8	120.20 (16)
O8—N3—C5	117.95 (16)	C10—C9—H9	119.9
O7—N3—C5	115.89 (17)	C8—C9—H9	119.9
O9—N4—O10	122.95 (17)	C9—C10—C11	120.58 (16)
O9—N4—C11	118.70 (16)	C9—C10—H10	119.7
O10—N4—C11	118.34 (15)	C11—C10—H10	119.7
O12—N5—O11	125.41 (19)	C10—C11—C12	119.36 (16)
O12—N5—C12	118.04 (18)	C10—C11—N4	118.98 (15)
O11—N5—C12	116.54 (17)	C12—C11—N4	121.66 (16)
O1—C1—C2	126.17 (16)	C7—C12—C11	121.61 (16)
O1—C1—C6	116.23 (15)	C7—C12—N5	117.27 (15)
C2—C1—C6	117.61 (16)	C11—C12—N5	121.06 (15)
C3—C2—C1	122.38 (16)	O1—C13—H13A	109.5
C3—C2—N1	116.34 (16)	O1—C13—H13B	109.5
C1—C2—N1	121.24 (17)	H13A—C13—H13B	109.5
C2—C3—C4	119.28 (16)	O1—C13—H13C	109.5
C2—C3—H3	120.4	H13A—C13—H13C	109.5
C4—C3—H3	120.4	H13B—C13—H13C	109.5
C3—C4—C5	119.40 (16)	O2—C14—H14A	109.5
C3—C4—N2	118.23 (16)	O2—C14—H14B	109.5
C5—C4—N2	122.31 (17)	H14A—C14—H14B	109.5
C6—C5—C4	121.87 (16)	O2—C14—H14C	109.5
C6—C5—N3	116.95 (15)	H14A—C14—H14C	109.5
C4—C5—N3	121.15 (15)	H14B—C14—H14C	109.5
C5—C6—C1	119.15 (15)

C13—O1—C1—C2	39.2 (3)	C2—C1—C6—C7	175.07 (15)
C13—O1—C1—C6	−141.22 (19)	C5—C6—C7—C12	−95.4 (2)
O1—C1—C2—C3	−174.24 (17)	C1—C6—C7—C12	84.4 (2)
C6—C1—C2—C3	6.2 (3)	C5—C6—C7—C8	84.9 (2)
O1—C1—C2—N1	8.1 (3)	C1—C6—C7—C8	−95.26 (19)
C6—C1—C2—N1	−171.47 (16)	C14—O2—C8—C9	−1.7 (3)
O4—N1—C2—C3	45.1 (3)	C14—O2—C8—C7	178.11 (16)
O3—N1—C2—C3	−132.0 (2)	C12—C7—C8—O2	−179.37 (14)
O4—N1—C2—C1	−137.1 (2)	C6—C7—C8—O2	0.3 (2)
O3—N1—C2—C1	45.8 (3)	C12—C7—C8—C9	0.4 (2)
C1—C2—C3—C4	−2.5 (3)	C6—C7—C8—C9	−179.88 (15)
N1—C2—C3—C4	175.21 (16)	O2—C8—C9—C10	−179.60 (15)
C2—C3—C4—C5	−2.2 (3)	C7—C8—C9—C10	0.6 (2)
C2—C3—C4—N2	175.03 (16)	C8—C9—C10—C11	−0.9 (3)
O5—N2—C4—C3	12.9 (3)	C9—C10—C11—C12	0.0 (2)
O6—N2—C4—C3	−166.04 (19)	C9—C10—C11—N4	−179.06 (15)
O5—N2—C4—C5	−170.01 (19)	O9—N4—C11—C10	6.8 (2)
O6—N2—C4—C5	11.1 (3)	O10—N4—C11—C10	−174.16 (19)
C3—C4—C5—C6	3.1 (3)	O9—N4—C11—C12	−172.27 (17)
N2—C4—C5—C6	−173.96 (16)	O10—N4—C11—C12	6.8 (3)
C3—C4—C5—N3	−174.78 (16)	C8—C7—C12—C11	−1.3 (2)
N2—C4—C5—N3	8.2 (3)	C6—C7—C12—C11	179.06 (15)
O8—N3—C5—C6	81.7 (2)	C8—C7—C12—N5	175.72 (15)
O7—N3—C5—C6	−95.50 (19)	C6—C7—C12—N5	−3.9 (2)
O8—N3—C5—C4	−100.3 (2)	C10—C11—C12—C7	1.0 (2)
O7—N3—C5—C4	82.5 (2)	N4—C11—C12—C7	−179.88 (15)
C4—C5—C6—C1	0.6 (3)	C10—C11—C12—N5	−175.84 (16)
N3—C5—C6—C1	178.61 (15)	N4—C11—C12—N5	3.2 (2)
C4—C5—C6—C7	−179.53 (15)	O12—N5—C12—C7	84.0 (2)
N3—C5—C6—C7	−1.6 (2)	O11—N5—C12—C7	−94.7 (2)
O1—C1—C6—C5	175.27 (15)	O12—N5—C12—C11	−99.0 (2)
C2—C1—C6—C5	−5.1 (2)	O11—N5—C12—C11	82.3 (2)
O1—C1—C6—C7	−4.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O3	0.96	2.45	2.926 (3)	111
C14—H14B···O10ⁱ	0.96	2.55	3.502 (3)	174
C14—H14C···O8ⁱⁱ	0.96	2.58	3.371 (3)	140

Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₉N₅O₁₂
M_r	439.26
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	10.3765 (13), 10.4423 (13), 10.4429 (13)
α, β, γ (°)	82.565 (1), 62.285 (1), 60.520 (1)
V (Å³)	864.73 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.41 × 0.34 × 0.29

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.940, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	6598, 3194, 2686
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.02
No. of reflections	3194
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O3	0.96	2.45	2.926 (3)	110.7
C14—H14B···O10ⁱ	0.96	2.55	3.502 (3)	173.9
C14—H14C···O8ⁱⁱ	0.96	2.58	3.371 (3)	140.2

Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by the Henan Innovation Project for University Prominent Research Talents (No. 2005 KYCX021), and the Natural Science Foundation of Henan Province.

References

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