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

The geometric parameters of the title compound, C(8)H(6)N(2)O·C(6)H(3)N(3)O(7), 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 mol-ecular conformation of the picric acid is stabilized by an intra-molecular O-H⋯O hydrogen bond. The phthalazin-1(2H)-one mol-ecules are connected via N-H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

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

Crystal data

C6H3N3O7·C8H6N2O

M = 375.26

Monoclinic,

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)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 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

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063362/at2514Isup2.hkl

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

C6H3N3O7·C8H6N2O	F000 = 768
Mr = 375.26	Dx = 1.656 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 18866 reflections
a = 6.9277 (4) Å	θ = 3.5–25.7º
b = 9.2087 (8) Å	µ = 0.14 mm−1
c = 23.6900 (15) Å	T = 173 (2) K
β = 95.246 (5)º	Block, yellow
V = 1504.98 (18) Å3	0.27 × 0.25 × 0.24 mm
Z = 4

Stoe IPDSII diffractometer	2384 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Monochromator: graphite	θmax = 25.6º
T = 173(2) K	θmin = 3.4º
ω scans	h = −8→8
Absorption correction: none	k = −11→11
18938 measured reflections	l = −28→28
2819 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.1404P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.22 e Å−3
2819 reflections	Δρmin = −0.18 e Å−3
253 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0119 (17)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
O1	0.66147 (14)	0.65518 (11)	0.51988 (4)	0.0300 (2)
N1	0.67645 (17)	0.48688 (13)	0.45056 (5)	0.0272 (3)
H1	0.562 (3)	0.445 (2)	0.4613 (8)	0.044 (5)*
N2	0.75780 (17)	0.41599 (13)	0.40757 (5)	0.0292 (3)
C1	0.74820 (18)	0.60533 (15)	0.48045 (5)	0.0240 (3)
C2	0.9215 (2)	0.46716 (16)	0.39350 (6)	0.0287 (3)
H2	0.9818	0.4186	0.3644	0.034*
C3	1.01736 (19)	0.59266 (15)	0.41912 (6)	0.0258 (3)
C4	1.1946 (2)	0.64606 (17)	0.40233 (6)	0.0303 (3)
H4	1.2568	0.5978	0.3735	0.036*
C5	1.2770 (2)	0.76868 (17)	0.42798 (6)	0.0318 (3)
H5	1.3962	0.8044	0.4167	0.038*
C6	1.1867 (2)	0.84098 (16)	0.47044 (6)	0.0310 (3)
H6	1.2441	0.9261	0.4873	0.037*
C7	1.0148 (2)	0.78938 (15)	0.48800 (6)	0.0271 (3)
H7	0.9549	0.8380	0.5172	0.033*
C8	0.92916 (18)	0.66482 (15)	0.46255 (5)	0.0236 (3)
C11	0.55633 (18)	0.74695 (14)	0.68594 (6)	0.0240 (3)
C12	0.58222 (18)	0.69094 (14)	0.74195 (6)	0.0235 (3)
C13	0.44722 (18)	0.71095 (14)	0.78092 (6)	0.0239 (3)
H13	0.4688	0.6721	0.8181	0.029*
C14	0.28010 (19)	0.78865 (14)	0.76467 (6)	0.0241 (3)
C15	0.24542 (19)	0.84793 (14)	0.71086 (6)	0.0249 (3)
H15	0.1298	0.9006	0.7003	0.030*
C16	0.38311 (19)	0.82836 (14)	0.67310 (6)	0.0242 (3)
N11	0.75280 (16)	0.60220 (13)	0.76171 (5)	0.0280 (3)
N12	0.13440 (16)	0.80502 (13)	0.80526 (5)	0.0279 (3)
N13	0.34405 (18)	0.89697 (13)	0.61722 (5)	0.0287 (3)
O11	0.68359 (15)	0.71926 (12)	0.64906 (5)	0.0332 (3)
H11	0.643 (4)	0.767 (3)	0.6170 (11)	0.075 (7)*
O12	0.89061 (14)	0.59522 (13)	0.73298 (5)	0.0405 (3)
O13	0.74780 (16)	0.53924 (14)	0.80712 (5)	0.0434 (3)
O14	0.15798 (15)	0.73720 (13)	0.84986 (4)	0.0392 (3)
O15	−0.00576 (15)	0.88503 (13)	0.79219 (5)	0.0397 (3)
O16	0.18568 (17)	0.95344 (12)	0.60558 (5)	0.0410 (3)
O17	0.47424 (16)	0.89587 (12)	0.58474 (4)	0.0374 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0242 (5)	0.0360 (6)	0.0314 (5)	−0.0009 (4)	0.0101 (4)	−0.0075 (4)
N1	0.0236 (6)	0.0319 (6)	0.0271 (6)	−0.0020 (5)	0.0077 (5)	−0.0047 (5)
N2	0.0285 (6)	0.0324 (6)	0.0277 (6)	0.0001 (5)	0.0073 (5)	−0.0043 (5)
C1	0.0201 (6)	0.0283 (7)	0.0237 (6)	0.0036 (5)	0.0021 (5)	0.0005 (5)
C2	0.0292 (7)	0.0329 (7)	0.0250 (7)	0.0025 (6)	0.0083 (5)	−0.0028 (6)
C3	0.0238 (6)	0.0303 (7)	0.0234 (7)	0.0036 (5)	0.0033 (5)	0.0041 (5)
C4	0.0271 (7)	0.0381 (8)	0.0270 (7)	0.0036 (6)	0.0090 (6)	0.0049 (6)
C5	0.0238 (7)	0.0401 (8)	0.0322 (8)	−0.0028 (6)	0.0056 (6)	0.0082 (6)
C6	0.0278 (7)	0.0317 (7)	0.0329 (8)	−0.0031 (6)	−0.0006 (6)	0.0037 (6)
C7	0.0249 (6)	0.0301 (7)	0.0262 (7)	0.0028 (5)	0.0020 (5)	−0.0007 (5)
C8	0.0192 (6)	0.0291 (7)	0.0226 (6)	0.0031 (5)	0.0024 (5)	0.0030 (5)
C11	0.0225 (6)	0.0228 (6)	0.0271 (7)	−0.0038 (5)	0.0045 (5)	−0.0047 (5)
C12	0.0193 (6)	0.0234 (6)	0.0275 (7)	−0.0001 (5)	0.0010 (5)	−0.0035 (5)
C13	0.0234 (6)	0.0238 (6)	0.0242 (7)	−0.0013 (5)	0.0007 (5)	−0.0018 (5)
C14	0.0211 (6)	0.0248 (6)	0.0269 (7)	−0.0010 (5)	0.0054 (5)	−0.0035 (5)
C15	0.0227 (6)	0.0223 (6)	0.0292 (7)	0.0000 (5)	0.0006 (5)	−0.0024 (5)
C16	0.0271 (7)	0.0213 (6)	0.0240 (7)	−0.0025 (5)	0.0010 (5)	−0.0009 (5)
N11	0.0232 (6)	0.0320 (6)	0.0282 (6)	0.0030 (5)	−0.0003 (5)	−0.0058 (5)
N12	0.0239 (6)	0.0298 (6)	0.0306 (6)	0.0008 (5)	0.0064 (5)	−0.0022 (5)
N13	0.0360 (7)	0.0248 (6)	0.0250 (6)	−0.0001 (5)	0.0015 (5)	−0.0017 (5)
O11	0.0300 (5)	0.0421 (6)	0.0291 (6)	0.0055 (4)	0.0108 (4)	0.0008 (5)
O12	0.0228 (5)	0.0580 (7)	0.0415 (6)	0.0097 (5)	0.0079 (4)	−0.0005 (5)
O13	0.0417 (6)	0.0551 (7)	0.0337 (6)	0.0212 (5)	0.0044 (5)	0.0100 (5)
O14	0.0337 (6)	0.0549 (7)	0.0304 (6)	0.0046 (5)	0.0101 (4)	0.0094 (5)
O15	0.0321 (6)	0.0410 (6)	0.0478 (7)	0.0143 (5)	0.0132 (5)	0.0035 (5)
O16	0.0471 (7)	0.0412 (6)	0.0336 (6)	0.0164 (5)	−0.0028 (5)	0.0029 (5)
O17	0.0432 (6)	0.0420 (6)	0.0280 (5)	−0.0031 (5)	0.0087 (5)	0.0034 (4)

O1—C1	1.2438 (17)	C11—C12	1.4198 (19)
N1—C1	1.3688 (18)	C11—C16	1.4240 (19)
N1—N2	1.3733 (16)	C12—C13	1.385 (2)
N1—H1	0.94 (2)	C12—N11	1.4772 (17)
N2—C2	1.2990 (19)	C13—C14	1.3853 (19)
C1—C8	1.4659 (19)	C13—H13	0.9500
C2—C3	1.439 (2)	C14—C15	1.387 (2)
C2—H2	0.9500	C14—N12	1.4640 (18)
C3—C8	1.4102 (19)	C15—C16	1.378 (2)
C3—C4	1.413 (2)	C15—H15	0.9500
C4—C5	1.381 (2)	C16—N13	1.4694 (17)
C4—H4	0.9500	N11—O12	1.2238 (16)
C5—C6	1.400 (2)	N11—O13	1.2255 (17)
C5—H5	0.9500	N12—O14	1.2255 (16)
C6—C7	1.381 (2)	N12—O15	1.2356 (16)
C6—H6	0.9500	N13—O16	1.2226 (16)
C7—C8	1.4019 (19)	N13—O17	1.2381 (17)
C7—H7	0.9500	O11—H11	0.90 (3)
C11—O11	1.3214 (17)
C1—N1—N2	127.46 (12)	O11—C11—C12	120.86 (12)
C1—N1—H1	117.8 (11)	O11—C11—C16	124.09 (13)
N2—N1—H1	114.7 (11)	C12—C11—C16	115.01 (12)
C2—N2—N1	116.41 (12)	C13—C12—C11	122.63 (12)
O1—C1—N1	120.34 (12)	C13—C12—N11	115.59 (12)
O1—C1—C8	124.33 (12)	C11—C12—N11	121.74 (12)
N1—C1—C8	115.34 (12)	C12—C13—C14	118.79 (12)
N2—C2—C3	124.27 (13)	C12—C13—H13	120.6
N2—C2—H2	117.9	C14—C13—H13	120.6
C3—C2—H2	117.9	C13—C14—C15	121.91 (13)
C8—C3—C4	119.14 (13)	C13—C14—N12	118.66 (12)
C8—C3—C2	118.16 (12)	C15—C14—N12	119.41 (12)
C4—C3—C2	122.69 (13)	C16—C15—C14	118.24 (12)
C5—C4—C3	119.70 (14)	C16—C15—H15	120.9
C5—C4—H4	120.1	C14—C15—H15	120.9
C3—C4—H4	120.1	C15—C16—C11	123.37 (13)
C4—C5—C6	120.74 (13)	C15—C16—N13	116.56 (12)
C4—C5—H5	119.6	C11—C16—N13	120.06 (12)
C6—C5—H5	119.6	O12—N11—O13	123.34 (12)
C7—C6—C5	120.45 (14)	O12—N11—C12	119.68 (12)
C7—C6—H6	119.8	O13—N11—C12	116.99 (11)
C5—C6—H6	119.8	O14—N12—O15	124.04 (12)
C6—C7—C8	119.64 (13)	O14—N12—C14	117.92 (11)
C6—C7—H7	120.2	O15—N12—C14	118.04 (12)
C8—C7—H7	120.2	O16—N13—O17	123.57 (12)
C7—C8—C3	120.31 (12)	O16—N13—C16	118.27 (12)
C7—C8—C1	121.39 (12)	O17—N13—C16	118.15 (12)
C3—C8—C1	118.29 (12)	C11—O11—H11	106.6 (16)
C1—N1—N2—C2	−0.1 (2)	C11—C12—C13—C14	0.0 (2)
N2—N1—C1—O1	−177.43 (12)	N11—C12—C13—C14	−177.71 (11)
N2—N1—C1—C8	2.34 (19)	C12—C13—C14—C15	−0.7 (2)
N1—N2—C2—C3	−1.3 (2)	C12—C13—C14—N12	177.76 (12)
N2—C2—C3—C8	0.3 (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—C11	1.9 (2)
C2—C3—C4—C5	178.79 (13)	C14—C15—C16—N13	−178.00 (11)
C3—C4—C5—C6	−0.1 (2)	O11—C11—C16—C15	175.42 (13)
C4—C5—C6—C7	1.0 (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—N13	177.46 (11)
C6—C7—C8—C1	179.16 (12)	C13—C12—N11—O12	−170.29 (12)
C4—C3—C8—C7	1.09 (19)	C11—C12—N11—O12	11.95 (19)
C2—C3—C8—C7	−178.64 (12)	C13—C12—N11—O13	9.31 (18)
C4—C3—C8—C1	−178.31 (12)	C11—C12—N11—O13	−168.45 (12)
C2—C3—C8—C1	1.96 (18)	C13—C14—N12—O14	−7.04 (19)
O1—C1—C8—C7	−2.7 (2)	C15—C14—N12—O14	171.43 (13)
N1—C1—C8—C7	177.49 (12)	C13—C14—N12—O15	173.74 (12)
O1—C1—C8—C3	176.65 (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—O16	172.73 (12)
C16—C11—C12—C13	1.42 (18)	C15—C16—N13—O17	171.79 (12)
O11—C11—C12—N11	1.12 (19)	C11—C16—N13—O17	−8.08 (18)
C16—C11—C12—N11	179.02 (11)

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)

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) .