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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o119
https://doi.org/10.1107/S1600536807063362

Phthalazin-1(2H)-one–picric acid (1/1)

H. S. Yathirajan,a B. Narayana,b M. T. Swamy,c B. K. Sarojinid and Michael Boltee*

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, cDepartment of Chemistry, Sambhram Institute of Technology, Bangalore 560 097, India, dDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India, and eInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str.7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 22 November 2007; accepted 26 November 2007; online 6 December 2007)

The geometric parameters of the title compound, C8H6N2O·C6H3N3O7, are in the usual ranges. The three nitro groups are almost coplanar with the aromatic picrate ring [dihedral angles 10.2 (2)°, 7.62 (16) and 8.08 (17)°]. The mol­ecular conformation of the picric acid is stabilized by an intra­molecular O—H⋯O hydrogen bond. The phthalazin-1(2H)-one mol­ecules are connected via N—H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For related literature, see: Büyükgüngör, Odabaşoğlu, Narayana, et al. (2007[Büyükgüngör, O., Odabaşoğlu, M., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3198.]); Büyükgüngör, Odabaşoğlu, Vijesh & Yathirajan (2007[Büyükgüngör, O., Odabaşoğlu, M., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4084-o4085.]); Balogh-Hergovich et al. (1997[Balogh-Hergovich, E., Kaizer, J. & Speier, G. (1997). Inorg. Chim. Acta, 256, 9-14.]); Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Vijesh, A. M. & Narayana, B. (2007). Acta Cryst. E63, o3674.]); Cheng et al. (1999[Cheng, Y., Ma, B. & Wuld, F. (1999). J. Mat. Chem. 9, 2183-2188.]); Coates (1999[Coates, W. J. (1999). In Comprehensive Heterocyclic Chemistry II, Vol. 6, edited by A. R. Katritzky, C. W. Rees & E. F. V. Scriven. Oxford: Pergamon Press.]); Harrison et al. (2007[Harrison, W. T. A., Ashok, M. A., Yathirajan, H. S. & Narayana Achar, B. (2007). Acta Cryst. E63, o3322.]); Li et al. (2006[Li, Y. X., Luo, Y. P., Xi, Z., Niu, C., He, Y. Z. & Yang, G. F. (2006). J. Agric. Food Chem. 54, 9135-9139.]); Porter (1979[Porter, A. E. A. (1979). In Comprehensive Organic Chemistry, Vol. 4, edited by A. R. Katritzky, D. Barton & W. D. Ollis. Oxford: Pergamon Press.]); Sarojini et al. (2007[Sarojini, B. K., Narayana, B., Swamy, M. T., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o4181.]); Shubin et al. (2004[Shubin, K. M., Kuznestsov, V. A. & Galishev, V. A. (2004). Tetrahedron Lett. 45, 1407-1408.]); Yatani et al. (2001[Yatani, A., Fuji, M., Nakao, Y., Kashino, S., Kinoshita, M., Mori, W. & Suzuki, S. (2001). Inorg. Chim. Acta, 316, 127-131.]).

[Scheme 1]

Experimental

Crystal data

  • C6H3N3O7·C8H6N2O

  • Mr = 375.26

  • Monoclinic, P 21 /n

  • a = 6.9277 (4) Å

  • b = 9.2087 (8) Å

  • c = 23.6900 (15) Å

  • β = 95.246 (5)°

  • V = 1504.98 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.14 mm−1

  • T = 173 (2) K

  • 0.27 × 0.25 × 0.24 mm
Data collection

  • Stoe IPDSII diffractometer

  • Absorption correction: none

  • 18938 measured reflections

  • 2819 independent reflections

  • 2384 reflections with I > 2σ(I)

  • Rint = 0.043
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.091

  • S = 1.02

  • 2819 reflections

  • 253 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.94 (2) 1.89 (2) 2.8252 (16) 175.2 (17)
O11—H11⋯O17 0.90 (3) 1.79 (3) 2.5819 (16) 146 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990[Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807063362/at2514sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063362/at2514Isup2.hkl

checkCIF report


Comment top

Phthalazines, also called benzo-orthodiazines or benzopyridazines, are a group of heterocyclic compounds isomeric with the cinnolines. The practical interest upon phthalazine derivatives is based on their widespread applications (Coates, 1999). Phthalazines, like others members of the isomeric diazine series, have found wide applications as therapeutic agents (Porter, 1979). Phthalazines are also commonly used as ligands in transition metal catalysis (Balogh-Hergovich et al., 1997 & Yatani et al., 2001), as chemiluminescent materials (Shubin et al., 2004) and for optical applications (Cheng et al., 1999). 2-Substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives are used as herbicides (Li et al., 2006). Structures of phthalazin-1(2H)-one (

Büyükgüngör, Odabaşoğlu, Narayana, Vijesh & Yathirajan, 2007), (1Z)-phthalazin-1(2H)-one isopropylidenehydrazone (Büyükgüngör, Odabaşoğlu, Vijesh & Yathirajan, 2007), 4-methoxybenzaldehyde (phthalazin-1-ylidene)hydrazone (Butcher et al., 2007) have been published. A similar structure was observed with phenothiazine-picric acid (Harrison et al., 2007). In continuation to our studies on the structures of picrates (Sarojini et al., 2007), a new cocrystal of phthalazin-1(2H)-one with picric acid was obtained when we prepared the picrate using the usual procedure and its crystal structure is reported.

Geometric parameters of the title compound are in the usual ranges. The three nitrogroups are almost coplanar with the aromatic picrate ring [dihedral angles 10.2 (2)°, 7.62 (16) and 8.08 (17)°]. The molecular conformation of the picric acid is stabilized by an intramolecular O—H···O hydrogen bond. The phthalazin-1(2H)-one molecules are connected via N—-H···O hydrogen bonds to form centrosymmetric dimers.

Related literature top

For related literature, see: Büyükgüngör, Odabaşoğlu, Narayana, et al. (2007); Büyükgüngör, Odabaşoğlu, Vijesh & Yathirajan (2007); Balogh-Hergovich et al. (1997); Butcher et al. (2007); Cheng et al. (1999); Coates (1999); Harrison et al. (2007); Li et al. (2006); Porter (1979); Sarojini et al. (2007); Shubin et al. (2004); Yatani et al. (2001).

Experimental top

Phthalazin-1(2H)-one (1.46 g, 0.01 mol) was dissolved in 25 ml of ethanol. Picric acid (2.29 g, 0.01 mol) was dissolved in 10 ml of water. Both the solutions were mixed and to this 5 ml of 5 M HCl was added and stirred for few minutes. The precipitate formed was filtered, dried and x-ray quality crystals were obtained by slow evaporation from absolute ethanol [m. p.: 403–405 K]. Composition: Found (Calculated): C 44.72 (44.81), H 2.39 (2.42), N 18.60% (18.66%).

Refinement top

H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [Uiso(H) = 1.2 Ueq(C)] using a riding model with C—H = 0.95 Å. H atoms bonded to N and O were freely refined.

Structure description top

Phthalazines, also called benzo-orthodiazines or benzopyridazines, are a group of heterocyclic compounds isomeric with the cinnolines. The practical interest upon phthalazine derivatives is based on their widespread applications (Coates, 1999). Phthalazines, like others members of the isomeric diazine series, have found wide applications as therapeutic agents (Porter, 1979). Phthalazines are also commonly used as ligands in transition metal catalysis (Balogh-Hergovich et al., 1997 & Yatani et al., 2001), as chemiluminescent materials (Shubin et al., 2004) and for optical applications (Cheng et al., 1999). 2-Substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives are used as herbicides (Li et al., 2006). Structures of phthalazin-1(2H)-one (

Büyükgüngör, Odabaşoğlu, Narayana, Vijesh & Yathirajan, 2007), (1Z)-phthalazin-1(2H)-one isopropylidenehydrazone (Büyükgüngör, Odabaşoğlu, Vijesh & Yathirajan, 2007), 4-methoxybenzaldehyde (phthalazin-1-ylidene)hydrazone (Butcher et al., 2007) have been published. A similar structure was observed with phenothiazine-picric acid (Harrison et al., 2007). In continuation to our studies on the structures of picrates (Sarojini et al., 2007), a new cocrystal of phthalazin-1(2H)-one with picric acid was obtained when we prepared the picrate using the usual procedure and its crystal structure is reported.

Geometric parameters of the title compound are in the usual ranges. The three nitrogroups are almost coplanar with the aromatic picrate ring [dihedral angles 10.2 (2)°, 7.62 (16) and 8.08 (17)°]. The molecular conformation of the picric acid is stabilized by an intramolecular O—H···O hydrogen bond. The phthalazin-1(2H)-one molecules are connected via N—-H···O hydrogen bonds to form centrosymmetric dimers.

For related literature, see: Büyükgüngör, Odabaşoğlu, Narayana, et al. (2007); Büyükgüngör, Odabaşoğlu, Vijesh & Yathirajan (2007); Balogh-Hergovich et al. (1997); Butcher et al. (2007); Cheng et al. (1999); Coates (1999); Harrison et al. (2007); Li et al. (2006); Porter (1979); Sarojini et al. (2007); Shubin et al. (2004); Yatani et al. (2001).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. The intramolecular hydrogen bond is shown as a dashed line.
Phthalazin-1(2H)-one–picric acid (1/1) top
Crystal data top
C6H3N3O7·C8H6N2OF(000) = 768
Mr = 375.26Dx = 1.656 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 18866 reflections
a = 6.9277 (4) Åθ = 3.5–25.7°
b = 9.2087 (8) ŵ = 0.14 mm−1
c = 23.6900 (15) ÅT = 173 K
β = 95.246 (5)°Block, yellow
V = 1504.98 (18) Å30.27 × 0.25 × 0.24 mm
Z = 4
Data collection top
Stoe IPDSII
diffractometer		2384 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 25.6°, θmin = 3.4°
ω scansh = −8→8
18938 measured reflectionsk = −11→11
2819 independent reflectionsl = −28→28
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0623P)2 + 0.1404P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2819 reflectionsΔρmax = 0.22 e Å−3
253 parametersΔρmin = −0.18 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0119 (17)
Crystal data top
C6H3N3O7·C8H6N2OV = 1504.98 (18) Å3
Mr = 375.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.9277 (4) ŵ = 0.14 mm−1
b = 9.2087 (8) ÅT = 173 K
c = 23.6900 (15) Å0.27 × 0.25 × 0.24 mm
β = 95.246 (5)°
Data collection top
Stoe IPDSII
diffractometer		2384 reflections with I > 2σ(I)
18938 measured reflectionsRint = 0.043
2819 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.22 e Å−3
2819 reflectionsΔρmin = −0.18 e Å−3
253 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
xyzUiso*/Ueq
O10.66147 (14)0.65518 (11)0.51988 (4)0.0300 (2)
N10.67645 (17)0.48688 (13)0.45056 (5)0.0272 (3)
H10.562 (3)0.445 (2)0.4613 (8)0.044 (5)*
N20.75780 (17)0.41599 (13)0.40757 (5)0.0292 (3)
C10.74820 (18)0.60533 (15)0.48045 (5)0.0240 (3)
C20.9215 (2)0.46716 (16)0.39350 (6)0.0287 (3)
H20.98180.41860.36440.034*
C31.01736 (19)0.59266 (15)0.41912 (6)0.0258 (3)
C41.1946 (2)0.64606 (17)0.40233 (6)0.0303 (3)
H41.25680.59780.37350.036*
C51.2770 (2)0.76868 (17)0.42798 (6)0.0318 (3)
H51.39620.80440.41670.038*
C61.1867 (2)0.84098 (16)0.47044 (6)0.0310 (3)
H61.24410.92610.48730.037*
C71.0148 (2)0.78938 (15)0.48800 (6)0.0271 (3)
H70.95490.83800.51720.033*
C80.92916 (18)0.66482 (15)0.46255 (5)0.0236 (3)
C110.55633 (18)0.74695 (14)0.68594 (6)0.0240 (3)
C120.58222 (18)0.69094 (14)0.74195 (6)0.0235 (3)
C130.44722 (18)0.71095 (14)0.78092 (6)0.0239 (3)
H130.46880.67210.81810.029*
C140.28010 (19)0.78865 (14)0.76467 (6)0.0241 (3)
C150.24542 (19)0.84793 (14)0.71086 (6)0.0249 (3)
H150.12980.90060.70030.030*
C160.38311 (19)0.82836 (14)0.67310 (6)0.0242 (3)
N110.75280 (16)0.60220 (13)0.76171 (5)0.0280 (3)
N120.13440 (16)0.80502 (13)0.80526 (5)0.0279 (3)
N130.34405 (18)0.89697 (13)0.61722 (5)0.0287 (3)
O110.68359 (15)0.71926 (12)0.64906 (5)0.0332 (3)
H110.643 (4)0.767 (3)0.6170 (11)0.075 (7)*
O120.89061 (14)0.59522 (13)0.73298 (5)0.0405 (3)
O130.74780 (16)0.53924 (14)0.80712 (5)0.0434 (3)
O140.15798 (15)0.73720 (13)0.84986 (4)0.0392 (3)
O15−0.00576 (15)0.88503 (13)0.79219 (5)0.0397 (3)
O160.18568 (17)0.95344 (12)0.60558 (5)0.0410 (3)
O170.47424 (16)0.89587 (12)0.58474 (4)0.0374 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0242 (5)0.0360 (6)0.0314 (5)−0.0009 (4)0.0101 (4)−0.0075 (4)
N10.0236 (6)0.0319 (6)0.0271 (6)−0.0020 (5)0.0077 (5)−0.0047 (5)
N20.0285 (6)0.0324 (6)0.0277 (6)0.0001 (5)0.0073 (5)−0.0043 (5)
C10.0201 (6)0.0283 (7)0.0237 (6)0.0036 (5)0.0021 (5)0.0005 (5)
C20.0292 (7)0.0329 (7)0.0250 (7)0.0025 (6)0.0083 (5)−0.0028 (6)
C30.0238 (6)0.0303 (7)0.0234 (7)0.0036 (5)0.0033 (5)0.0041 (5)
C40.0271 (7)0.0381 (8)0.0270 (7)0.0036 (6)0.0090 (6)0.0049 (6)
C50.0238 (7)0.0401 (8)0.0322 (8)−0.0028 (6)0.0056 (6)0.0082 (6)
C60.0278 (7)0.0317 (7)0.0329 (8)−0.0031 (6)−0.0006 (6)0.0037 (6)
C70.0249 (6)0.0301 (7)0.0262 (7)0.0028 (5)0.0020 (5)−0.0007 (5)
C80.0192 (6)0.0291 (7)0.0226 (6)0.0031 (5)0.0024 (5)0.0030 (5)
C110.0225 (6)0.0228 (6)0.0271 (7)−0.0038 (5)0.0045 (5)−0.0047 (5)
C120.0193 (6)0.0234 (6)0.0275 (7)−0.0001 (5)0.0010 (5)−0.0035 (5)
C130.0234 (6)0.0238 (6)0.0242 (7)−0.0013 (5)0.0007 (5)−0.0018 (5)
C140.0211 (6)0.0248 (6)0.0269 (7)−0.0010 (5)0.0054 (5)−0.0035 (5)
C150.0227 (6)0.0223 (6)0.0292 (7)0.0000 (5)0.0006 (5)−0.0024 (5)
C160.0271 (7)0.0213 (6)0.0240 (7)−0.0025 (5)0.0010 (5)−0.0009 (5)
N110.0232 (6)0.0320 (6)0.0282 (6)0.0030 (5)−0.0003 (5)−0.0058 (5)
N120.0239 (6)0.0298 (6)0.0306 (6)0.0008 (5)0.0064 (5)−0.0022 (5)
N130.0360 (7)0.0248 (6)0.0250 (6)−0.0001 (5)0.0015 (5)−0.0017 (5)
O110.0300 (5)0.0421 (6)0.0291 (6)0.0055 (4)0.0108 (4)0.0008 (5)
O120.0228 (5)0.0580 (7)0.0415 (6)0.0097 (5)0.0079 (4)−0.0005 (5)
O130.0417 (6)0.0551 (7)0.0337 (6)0.0212 (5)0.0044 (5)0.0100 (5)
O140.0337 (6)0.0549 (7)0.0304 (6)0.0046 (5)0.0101 (4)0.0094 (5)
O150.0321 (6)0.0410 (6)0.0478 (7)0.0143 (5)0.0132 (5)0.0035 (5)
O160.0471 (7)0.0412 (6)0.0336 (6)0.0164 (5)−0.0028 (5)0.0029 (5)
O170.0432 (6)0.0420 (6)0.0280 (5)−0.0031 (5)0.0087 (5)0.0034 (4)
Geometric parameters (Å, º) top
O1—C11.2438 (17)C11—C121.4198 (19)
N1—C11.3688 (18)C11—C161.4240 (19)
N1—N21.3733 (16)C12—C131.385 (2)
N1—H10.94 (2)C12—N111.4772 (17)
N2—C21.2990 (19)C13—C141.3853 (19)
C1—C81.4659 (19)C13—H130.9500
C2—C31.439 (2)C14—C151.387 (2)
C2—H20.9500C14—N121.4640 (18)
C3—C81.4102 (19)C15—C161.378 (2)
C3—C41.413 (2)C15—H150.9500
C4—C51.381 (2)C16—N131.4694 (17)
C4—H40.9500N11—O121.2238 (16)
C5—C61.400 (2)N11—O131.2255 (17)
C5—H50.9500N12—O141.2255 (16)
C6—C71.381 (2)N12—O151.2356 (16)
C6—H60.9500N13—O161.2226 (16)
C7—C81.4019 (19)N13—O171.2381 (17)
C7—H70.9500O11—H110.90 (3)
C11—O111.3214 (17)
C1—N1—N2127.46 (12)O11—C11—C12120.86 (12)
C1—N1—H1117.8 (11)O11—C11—C16124.09 (13)
N2—N1—H1114.7 (11)C12—C11—C16115.01 (12)
C2—N2—N1116.41 (12)C13—C12—C11122.63 (12)
O1—C1—N1120.34 (12)C13—C12—N11115.59 (12)
O1—C1—C8124.33 (12)C11—C12—N11121.74 (12)
N1—C1—C8115.34 (12)C12—C13—C14118.79 (12)
N2—C2—C3124.27 (13)C12—C13—H13120.6
N2—C2—H2117.9C14—C13—H13120.6
C3—C2—H2117.9C13—C14—C15121.91 (13)
C8—C3—C4119.14 (13)C13—C14—N12118.66 (12)
C8—C3—C2118.16 (12)C15—C14—N12119.41 (12)
C4—C3—C2122.69 (13)C16—C15—C14118.24 (12)
C5—C4—C3119.70 (14)C16—C15—H15120.9
C5—C4—H4120.1C14—C15—H15120.9
C3—C4—H4120.1C15—C16—C11123.37 (13)
C4—C5—C6120.74 (13)C15—C16—N13116.56 (12)
C4—C5—H5119.6C11—C16—N13120.06 (12)
C6—C5—H5119.6O12—N11—O13123.34 (12)
C7—C6—C5120.45 (14)O12—N11—C12119.68 (12)
C7—C6—H6119.8O13—N11—C12116.99 (11)
C5—C6—H6119.8O14—N12—O15124.04 (12)
C6—C7—C8119.64 (13)O14—N12—C14117.92 (11)
C6—C7—H7120.2O15—N12—C14118.04 (12)
C8—C7—H7120.2O16—N13—O17123.57 (12)
C7—C8—C3120.31 (12)O16—N13—C16118.27 (12)
C7—C8—C1121.39 (12)O17—N13—C16118.15 (12)
C3—C8—C1118.29 (12)C11—O11—H11106.6 (16)
C1—N1—N2—C2−0.1 (2)C11—C12—C13—C140.0 (2)
N2—N1—C1—O1−177.43 (12)N11—C12—C13—C14−177.71 (11)
N2—N1—C1—C82.34 (19)C12—C13—C14—C15−0.7 (2)
N1—N2—C2—C3−1.3 (2)C12—C13—C14—N12177.76 (12)
N2—C2—C3—C80.3 (2)C13—C14—C15—C16−0.2 (2)
N2—C2—C3—C4−179.38 (13)N12—C14—C15—C16−178.67 (12)
C8—C3—C4—C5−0.9 (2)C14—C15—C16—C111.9 (2)
C2—C3—C4—C5178.79 (13)C14—C15—C16—N13−178.00 (11)
C3—C4—C5—C6−0.1 (2)O11—C11—C16—C15175.42 (13)
C4—C5—C6—C71.0 (2)C12—C11—C16—C15−2.40 (19)
C5—C6—C7—C8−0.8 (2)O11—C11—C16—N13−4.7 (2)
C6—C7—C8—C3−0.22 (19)C12—C11—C16—N13177.46 (11)
C6—C7—C8—C1179.16 (12)C13—C12—N11—O12−170.29 (12)
C4—C3—C8—C71.09 (19)C11—C12—N11—O1211.95 (19)
C2—C3—C8—C7−178.64 (12)C13—C12—N11—O139.31 (18)
C4—C3—C8—C1−178.31 (12)C11—C12—N11—O13−168.45 (12)
C2—C3—C8—C11.96 (18)C13—C14—N12—O14−7.04 (19)
O1—C1—C8—C7−2.7 (2)C15—C14—N12—O14171.43 (13)
N1—C1—C8—C7177.49 (12)C13—C14—N12—O15173.74 (12)
O1—C1—C8—C3176.65 (12)C15—C14—N12—O15−7.79 (19)
N1—C1—C8—C3−3.12 (17)C15—C16—N13—O16−7.40 (18)
O11—C11—C12—C13−176.48 (12)C11—C16—N13—O16172.73 (12)
C16—C11—C12—C131.42 (18)C15—C16—N13—O17171.79 (12)
O11—C11—C12—N111.12 (19)C11—C16—N13—O17−8.08 (18)
C16—C11—C12—N11179.02 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.94 (2)1.89 (2)2.8252 (16)175.2 (17)
O11—H11···O170.90 (3)1.79 (3)2.5819 (16)146 (2)
Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC6H3N3O7·C8H6N2O
Mr375.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)6.9277 (4), 9.2087 (8), 23.6900 (15)
β (°) 95.246 (5)
V (Å3)1504.98 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.14
Crystal size (mm)0.27 × 0.25 × 0.24
Data collection
DiffractometerStoe IPDSII
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		18938, 2819, 2384
Rint0.043
(sin θ/λ)max (Å−1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.091, 1.02
No. of reflections2819
No. of parameters253
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.22, −0.18

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.94 (2)1.89 (2)2.8252 (16)175.2 (17)
O11—H11···O170.90 (3)1.79 (3)2.5819 (16)146 (2)
Symmetry code: (i) −x+1, −y+1, −z+1.
 

Acknowledgements

HSY thanks the University of Mysore for research facilities.

References

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o119
https://doi.org/10.1107/S1600536807063362
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