4-Hydr­oxy-6-[(4-hydr­oxy-1-oxo-1,2-dihydro­phthalazin-6-yl)carbon­yl]phthalazin-1(2H)-one

Zhou, R.-S.; Song, J.-F.

doi:10.1107/S1600536809046509

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3050

doi:10.1107/S1600536809046509

Open

access

4-Hydroxy-6-[(4-hydroxy-1-oxo-1,2-dihydrophthalazin-6-yl)carbonyl]phthalazin-1(2H)-one

Rui-Sha Zhou ^a and Jiang-Feng Song ^a ^*

^aDepartment of Chemistry, North University of China, Taiyuan, Shanxi 030051, People's Republic of China
^*Correspondence e-mail: jfsong0129@gmail.com

(Received 16 October 2009; accepted 4 November 2009; online 11 November 2009)

In the crystal structure of the title compound, C₁₇H₁₀N₄O₅, the molecules lie on twofold axes (through the ketone bridge C and O atoms). The dihedral angle between the two phthalazine rings is 52.25 (1)°. In the crystal, intermolecular N—H⋯O and O—H⋯O interactions link the molecules.

Related literature

For the acylate reaction of polycarboxylate with hydrazine hydrate, see: Benniston et al. (1999 ); Hu et al. (2004 ).

Experimental

Crystal data

C₁₇H₁₀N₄O₅
M_r = 350.29
Monoclinic, C 2/c
a = 11.576 (3) Å
b = 10.511 (3) Å
c = 12.274 (3) Å
β = 111.718 (4)°
V = 1387.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1995 ) T_min = 0.963, T_max = 0.987
3800 measured reflections
1370 independent reflections
774 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.161
S = 0.99
1370 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.85	1.76	2.581 (3)	163
N2—H2⋯O1ⁱⁱ	0.86	2.19	3.034 (4)	168
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046509/jh2110sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046509/jh2110Isup2.hkl

checkCIF report

Comment top

In situ hydrothermal acylate reaction of multidentate aromatic polycarboxylate with hydrazine hydrate has been investigated (Benniston et al., 1999; Hu et al., 2004). We intend to select 3, 3'-4, 4'-benzophenonetetracarboxylic dianhydride as the ligand to continue the exploration of the in situ acylate reaction. However, the crystals of the title compound were obtained unintentionally as the harvested product of the hydrothermal reaction of 3, 3'-4, 4'-benzophenonetetracarboxylic dianhydride, CoCl₂ and hydrazine hydrate. In the title compound, a twofold axis lies in the C atom and O atom of the ketone bridge (Fig. 1). Each organic molecule connects six adjacent ones into a three-dimensional supramolecular network by intermolecular O—H···O (2.576 Å) and N—H···O (3.034 Å) hydrogen bonds (Fig. 2 and Fig. 3).

Related literature top

For the acylate reaction of polycarboxylate with hydrazine hydrate, see: Benniston et al. (1999); Hu et al. (2004).

Experimental top

Yellow needle-like crystals of the title compound were synthesized hydrothermally from a mixture of CoCl₂.H₂O (0.0230 g), 3, 3'-4, 4'-benzophenonetetracarboxylic dianhydride (0.0641 g), hydrazine hydrate (0.028 ml), and deionized water (15 ml) in a 23 ml Teflon-lined stainless steel autoclave under autogenous pressure heated to 170 °C for 4 days and cooled to room temperature. Crystalline product was filtered, washed with distilled water, and dried at ambient temperature.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound shown with 30% probabilty ellipsoids [symmetry code: (A) 1 - x, y, 1.5 - z].
	Fig. 2. View of the crystal packing of the title compound, with O—H···O and N—H···O hydrogen bonds drawn as dashed lines [see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity].
	Fig. 3. Three-dimensional network formed by hydrogen bonds (dashed lines).

4-Hydroxy-6-[(4-hydroxy-1-oxo-1,2-dihydrophthalazin-6-yl)carbonyl]phthalazin- 1(2H)-one top

Crystal data top

C₁₇H₁₀N₄O₅	F(000) = 720
M_r = 350.29	D_x = 1.677 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.576 (3) Å	θ = 2.7–26.0°
b = 10.511 (3) Å	µ = 0.13 mm⁻¹
c = 12.274 (3) Å	T = 293 K
β = 111.718 (4)°	Needle-like, yellow
V = 1387.4 (6) Å³	0.30 × 0.25 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	1370 independent reflections
Radiation source: fine-focus sealed tube	774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω scans	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	h = −14→12
T_min = 0.963, T_max = 0.987	k = −12→12
3800 measured reflections	l = −15→14

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0758P)²] where P = (F_o² + 2F_c²)/3
1370 reflections	(Δ/σ)_max = 0.005
120 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₁₀N₄O₅	V = 1387.4 (6) Å³
M_r = 350.29	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 11.576 (3) Å	µ = 0.13 mm⁻¹
b = 10.511 (3) Å	T = 293 K
c = 12.274 (3) Å	0.30 × 0.25 × 0.10 mm
β = 111.718 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	1370 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	774 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.987	R_int = 0.057
3800 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 0.99	Δρ_max = 0.27 e Å⁻³
1370 reflections	Δρ_min = −0.22 e Å⁻³
120 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
O3	0.5000	−0.2105 (3)	0.7500	0.0411 (9)
O1	0.1272 (2)	0.0713 (2)	0.23363 (19)	0.0468 (7)
H1	0.0902	0.1164	0.1732	0.070*
O2	0.5078 (2)	0.3361 (2)	0.5277 (2)	0.0512 (8)
N1	0.2410 (3)	0.2518 (3)	0.2824 (2)	0.0406 (8)
N2	0.3389 (3)	0.3149 (3)	0.3641 (2)	0.0367 (8)
H2	0.3513	0.3916	0.3467	0.044*
C6	0.3861 (3)	0.1464 (3)	0.5017 (3)	0.0303 (8)
C9	0.2158 (3)	0.1394 (3)	0.3114 (3)	0.0356 (9)
C5	0.2831 (3)	0.0802 (3)	0.4238 (2)	0.0314 (8)
C4	0.2480 (3)	−0.0367 (3)	0.4556 (3)	0.0362 (9)
H4	0.1781	−0.0790	0.4052	0.043*
C7	0.4564 (3)	0.0920 (3)	0.6103 (2)	0.0320 (8)
H5	0.5254	0.1346	0.6620	0.038*
C8	0.4182 (3)	0.2707 (3)	0.4689 (3)	0.0340 (8)
C3	0.3181 (3)	−0.0884 (3)	0.5624 (3)	0.0363 (9)
H3	0.2956	−0.1668	0.5835	0.044*
C1	0.5000	−0.0954 (4)	0.7500	0.0281 (10)
C2	0.4228 (3)	−0.0255 (3)	0.6404 (2)	0.0297 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.046 (2)	0.030 (2)	0.0369 (19)	0.000	0.0043 (17)	0.000
O1	0.0448 (16)	0.0439 (16)	0.0330 (14)	−0.0014 (13)	−0.0076 (12)	0.0032 (11)
O2	0.0573 (18)	0.0442 (16)	0.0328 (14)	−0.0200 (14)	−0.0057 (13)	0.0032 (12)
N1	0.0419 (18)	0.0406 (19)	0.0291 (15)	0.0021 (15)	0.0011 (14)	−0.0015 (13)
N2	0.0413 (18)	0.0273 (16)	0.0286 (15)	−0.0031 (13)	−0.0020 (14)	0.0025 (12)
C6	0.033 (2)	0.032 (2)	0.0226 (16)	−0.0007 (15)	0.0059 (16)	−0.0040 (14)
C9	0.038 (2)	0.033 (2)	0.0260 (18)	0.0018 (17)	0.0002 (17)	−0.0027 (15)
C5	0.0308 (19)	0.033 (2)	0.0254 (16)	0.0047 (16)	0.0051 (15)	−0.0033 (14)
C4	0.037 (2)	0.032 (2)	0.0297 (18)	−0.0059 (16)	0.0016 (17)	−0.0023 (15)
C7	0.0294 (19)	0.035 (2)	0.0231 (17)	−0.0043 (16)	−0.0001 (15)	−0.0035 (14)
C8	0.038 (2)	0.033 (2)	0.0254 (17)	−0.0009 (17)	0.0053 (16)	−0.0021 (15)
C3	0.039 (2)	0.033 (2)	0.0302 (18)	−0.0042 (17)	0.0050 (16)	−0.0010 (16)
C1	0.028 (3)	0.024 (3)	0.027 (2)	0.000	0.005 (2)	0.000
C2	0.035 (2)	0.030 (2)	0.0217 (17)	0.0007 (15)	0.0074 (16)	−0.0046 (13)

Geometric parameters (Å, º) top

O3—C1	1.210 (5)	C9—C5	1.450 (4)
O1—C9	1.323 (4)	C5—C4	1.394 (4)
O1—H1	0.8501	C4—C3	1.373 (4)
O2—C8	1.231 (4)	C4—H4	0.9300
N1—C9	1.298 (4)	C7—C2	1.386 (4)
N1—N2	1.374 (4)	C7—H5	0.9300
N2—C8	1.357 (4)	C3—C2	1.401 (4)
N2—H2	0.8600	C3—H3	0.9300
C6—C7	1.401 (4)	C1—C2ⁱ	1.502 (4)
C6—C5	1.406 (4)	C1—C2	1.502 (4)
C6—C8	1.455 (5)

C9—O1—H1	109.5	C5—C4—H4	120.5
C9—N1—N2	116.6 (3)	C2—C7—C6	119.7 (3)
C8—N2—N1	127.8 (3)	C2—C7—H5	120.1
C8—N2—H2	116.1	C6—C7—H5	120.1
N1—N2—H2	116.1	O2—C8—N2	119.5 (3)
C7—C6—C5	119.5 (3)	O2—C8—C6	125.8 (3)
C7—C6—C8	120.8 (3)	N2—C8—C6	114.6 (3)
C5—C6—C8	119.7 (3)	C4—C3—C2	121.5 (3)
N1—C9—O1	119.2 (3)	C4—C3—H3	119.3
N1—C9—C5	123.8 (3)	C2—C3—H3	119.3
O1—C9—C5	117.0 (3)	O3—C1—C2ⁱ	119.3 (2)
C4—C5—C6	120.5 (3)	O3—C1—C2	119.3 (2)
C4—C5—C9	122.3 (3)	C2ⁱ—C1—C2	121.5 (4)
C6—C5—C9	117.2 (3)	C7—C2—C3	119.7 (3)
C3—C4—C5	119.0 (3)	C7—C2—C1	122.8 (3)
C3—C4—H4	120.5	C3—C2—C1	117.3 (3)

C9—N1—N2—C8	4.9 (5)	N1—N2—C8—O2	173.9 (3)
N2—N1—C9—O1	−176.2 (3)	N1—N2—C8—C6	−6.8 (5)
N2—N1—C9—C5	1.1 (5)	C7—C6—C8—O2	2.4 (5)
C7—C6—C5—C4	2.4 (5)	C5—C6—C8—O2	−177.7 (3)
C8—C6—C5—C4	−177.5 (3)	C7—C6—C8—N2	−176.8 (3)
C7—C6—C5—C9	−178.3 (3)	C5—C6—C8—N2	3.1 (4)
C8—C6—C5—C9	1.8 (5)	C5—C4—C3—C2	0.8 (5)
N1—C9—C5—C4	175.2 (3)	C6—C7—C2—C3	−0.6 (5)
O1—C9—C5—C4	−7.5 (5)	C6—C7—C2—C1	174.2 (3)
N1—C9—C5—C6	−4.1 (5)	C4—C3—C2—C7	0.6 (5)
O1—C9—C5—C6	173.2 (3)	C4—C3—C2—C1	−174.4 (3)
C6—C5—C4—C3	−2.4 (5)	O3—C1—C2—C7	−148.7 (2)
C9—C5—C4—C3	178.4 (3)	C2ⁱ—C1—C2—C7	31.3 (2)
C5—C6—C7—C2	−0.9 (5)	O3—C1—C2—C3	26.2 (3)
C8—C6—C7—C2	179.0 (3)	C2ⁱ—C1—C2—C3	−153.8 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱⁱ	0.85	1.76	2.581 (3)	163
N2—H2···O1ⁱⁱⁱ	0.86	2.19	3.034 (4)	168

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀N₄O₅
M_r	350.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	11.576 (3), 10.511 (3), 12.274 (3)
β (°)	111.718 (4)
V (Å³)	1387.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1995)
T_min, T_max	0.963, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	3800, 1370, 774
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.161, 0.99
No. of reflections	1370
No. of parameters	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), 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
O1—H1···O2ⁱ	0.85	1.76	2.581 (3)	162.5
N2—H2···O1ⁱⁱ	0.86	2.19	3.034 (4)	168.3

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

Acknowledgements

This work was supported by the Doctoral Foundation of North University of China.

References

Benniston, A. C., Yufit, D. S. & Howard, J. A. K. (1999). Acta Cryst. C55, 1535–1536. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (1999). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, X. X., Xu, J. Q., Cheng, P., Chen, X. Y., Cui, X. B., Song, J. F., Yang, G. D. & Wang, T. G. (2004). Inorg. Chem. 43, 2261–2266. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1995). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. 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 65| Part 12| December 2009| Page o3050

doi:10.1107/S1600536809046509

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

4-Hydr­­oxy-6-[(4-hydr­­oxy-1-oxo-1,2-di­hydro­phthalazin-6-yl)carbon­yl]phthalazin-1(2H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Hydroxy-6-[(4-hydroxy-1-oxo-1,2-dihydrophthalazin-6-yl)carbonyl]phthalazin-1(2H)-one