2-Hydroxy­benzoic acid–purin-6-amine (3/1)

Du, L.; Zeng, W.; Liu, X.; Jian, F.-F.

doi:10.1107/S1600536809025240

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1791

doi:10.1107/S1600536809025240

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2-Hydroxybenzoic acid–purin-6-amine (3/1)

Lian-cai Du,^a Wu-lan Zeng,^b Xue-ying Liu ^a and Fang-Fang Jian ^c ^*

^aMicroscale Science Institute, Department of Biological Engineering, Weifang University, Weifang 261061, People's Republic of China, ^bMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^cMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 6 June 2009; accepted 30 June 2009; online 8 July 2009)

In the title 3:1 adduct, 3C₇H₆O₃·C₅H₅N₅, an intramolecular O—H⋯O hydrogen bond occurs in each of the three 2-hydroxybenzoic acid molecules. In the crystal, the components are linked by N—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For medicinal background, see: Forsythe & Ennis (1999 ).

Experimental

Crystal data

3C₇H₆O₃·C₅H₅N₅
M_r = 549.49
Monoclinic, P 2₁ /c
a = 10.998 (2) Å
b = 10.053 (2) Å
c = 23.490 (7) Å
β = 106.98 (3)°
V = 2483.9 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.38 × 0.22 × 0.14 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: none
22329 measured reflections
5680 independent reflections
4872 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.116
S = 1.06
5680 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯O3	0.82	1.87	2.5946 (17)	146
O4—H4B⋯O5	0.82	1.89	2.6111 (18)	146
O7—H7A⋯O9	0.82	1.89	2.6118 (15)	146
O2—H2C⋯N4ⁱ	0.82	1.87	2.6795 (18)	167
O6—H6B⋯N3ⁱⁱ	0.82	1.82	2.6305 (18)	172
O8—H8B⋯N2ⁱⁱⁱ	0.82	1.78	2.5864 (17)	168
N1—H1A⋯O9ⁱⁱⁱ	0.86	2.09	2.9302 (17)	167
N1—H1B⋯O3ⁱ	0.86	2.01	2.8593 (18)	171
N5—H5A⋯O7ⁱⁱ	0.86	2.14	2.8585 (17)	141
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+2, -z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S1600536809025240/hb5001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025240/hb5001Isup2.hkl

checkCIF report

Comment top

Adenine and its derivatives are an important class of compounds because they exhibit better pharmacological activities such as penicillins,antibiotics (Forsythe & Ennis, 1999). We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new adenine compounds with higher bioactivity.

The adenine ring system is essentially planar, with a dihedral angle of 0.37 (8) between the ring (atoms N4/N5/C24—C26) and the ring (N2/N3/C22—C25). The dihedral angles between the mean planes of the adenine system and rings (C1—C6) and rings (C8—C13) and rings (C15—C20) are 2.41 (7) and 85.83 (7)and 80.3 (7), respectively. The dihedral angle between rings(C1—C6) and rings (C8—C13) is 84.02 (8). In the crystal structure, weak inter molecular C—H···O hydrogen bonds and intramolecular O—H···O hydrogen-bond interactions to stabilize the crystal structure (Table 1). The packing (Fig.2) is further stabilized by weak O—H···O interactions.

Related literature top

For medicinal background, see: Forsythe & Ennis (1999).

Experimental top

Adenine 1.35 g(0.01 mol) and 2-hydroxybenzoic acid 4.14 g(0.03 mol) with ethanol were stirred for 18 h at 353 K. The solution was then filtered and concentrated to afford the white title compound 3.63 g (yield 70%). Colourless blocks of (I) were obtained by slow evaporation of an ethanol-water (10:1 v/v) solution at room temperature over a period of one week.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. The molecular structure of (I), drawn with 30% probability ellipsoids.

2-Hydroxybenzoic acid–purin-6-amine (3/1) top

Crystal data top

3C₇H₆O₃·C₅H₅N₅	F(000) = 1144
M_r = 549.49	D_x = 1.469 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5680 reflections
a = 10.998 (2) Å	θ = 3.0–27.5°
b = 10.053 (2) Å	µ = 0.11 mm⁻¹
c = 23.490 (7) Å	T = 293 K
β = 106.98 (3)°	Block, colourless
V = 2483.9 (10) Å³	0.38 × 0.22 × 0.14 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	4872 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −14→14
22329 measured reflections	k = −13→12
5680 independent reflections	l = −30→30

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) = 0.116	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0624P)² + 1.1319P] where P = (F_o² + 2F_c²)/3
5680 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

3C₇H₆O₃·C₅H₅N₅	V = 2483.9 (10) Å³
M_r = 549.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.998 (2) Å	µ = 0.11 mm⁻¹
b = 10.053 (2) Å	T = 293 K
c = 23.490 (7) Å	0.38 × 0.22 × 0.14 mm
β = 106.98 (3)°

Data collection top

Siemens SMART CCD diffractometer	4872 reflections with I > 2σ(I)
22329 measured reflections	R_int = 0.020
5680 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.06	Δρ_max = 0.83 e Å⁻³
5680 reflections	Δρ_min = −0.30 e Å⁻³
361 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	0.58987 (11)	0.54268 (12)	0.10882 (5)	0.0328 (3)
H1D	0.6464	0.5035	0.0993	0.049*
O2	0.70858 (10)	0.59642 (10)	−0.04308 (4)	0.0222 (2)
H2C	0.7663	0.5468	−0.0451	0.033*
O3	0.73581 (9)	0.48786 (10)	0.04287 (4)	0.0216 (2)
C1	0.42191 (15)	0.83244 (16)	−0.01407 (8)	0.0309 (3)
H1C	0.3832	0.8986	−0.0410	0.037*
C2	0.38415 (14)	0.81020 (16)	0.03701 (7)	0.0290 (3)
H2B	0.3200	0.8621	0.0440	0.035*
C3	0.44049 (14)	0.71264 (16)	0.07710 (7)	0.0258 (3)
H3B	0.4136	0.6985	0.1106	0.031*
C4	0.53780 (13)	0.63482 (14)	0.06763 (6)	0.0207 (3)
C5	0.57687 (13)	0.65547 (14)	0.01619 (6)	0.0190 (3)
C6	0.51750 (14)	0.75499 (15)	−0.02417 (7)	0.0254 (3)
H6A	0.5427	0.7691	−0.0582	0.030*
C7	0.67994 (13)	0.57290 (14)	0.00646 (6)	0.0184 (3)
O4	0.24665 (11)	0.29192 (11)	0.20033 (5)	0.0290 (2)
H4B	0.2049	0.2650	0.2217	0.043*
O5	0.18452 (10)	0.26468 (11)	0.29882 (5)	0.0279 (2)
O6	0.27892 (10)	0.39746 (11)	0.37517 (4)	0.0254 (2)
H6B	0.2255	0.3646	0.3891	0.038*
C8	0.54365 (13)	0.53292 (16)	0.29552 (7)	0.0242 (3)
H8A	0.6111	0.5862	0.3164	0.029*
C9	0.52558 (14)	0.50464 (17)	0.23539 (7)	0.0279 (3)
H9A	0.5809	0.5405	0.2162	0.033*
C10	0.42685 (15)	0.42432 (17)	0.20407 (7)	0.0277 (3)
H10A	0.4161	0.4064	0.1641	0.033*
C11	0.34292 (13)	0.36986 (15)	0.23260 (6)	0.0222 (3)
C12	0.35880 (13)	0.39957 (14)	0.29283 (6)	0.0189 (3)
C13	0.46011 (13)	0.48074 (14)	0.32360 (6)	0.0202 (3)
H13A	0.4713	0.4998	0.3635	0.024*
C14	0.26650 (13)	0.34705 (14)	0.32213 (6)	0.0199 (3)
N1	0.08652 (11)	0.72297 (12)	−0.04856 (5)	0.0205 (2)
H1A	0.0719	0.7725	−0.0797	0.025*
H1B	0.1424	0.6607	−0.0429	0.025*
N2	−0.06434 (11)	0.84210 (12)	−0.01967 (5)	0.0193 (2)
N3	−0.12090 (11)	0.80213 (12)	0.06983 (5)	0.0208 (2)
N4	0.11815 (11)	0.56210 (12)	0.06827 (5)	0.0194 (2)
N5	0.00044 (11)	0.61900 (12)	0.12747 (5)	0.0200 (2)
H5A	−0.0296	0.6176	0.1574	0.024*
C22	0.02299 (12)	0.74279 (14)	−0.00930 (6)	0.0173 (3)
C23	−0.12982 (13)	0.86541 (15)	0.01934 (6)	0.0218 (3)
H23A	−0.1886	0.9344	0.0098	0.026*
C24	−0.03382 (12)	0.70387 (14)	0.08015 (6)	0.0176 (3)
C25	0.03992 (12)	0.66798 (14)	0.04351 (5)	0.0169 (3)
C26	0.09105 (13)	0.53725 (15)	0.11826 (6)	0.0210 (3)
H26A	0.1301	0.4703	0.1446	0.025*
O7	−0.00080 (10)	1.02622 (10)	0.25745 (4)	0.0227 (2)
H7A	−0.0214	1.0709	0.2269	0.034*
O8	0.13258 (9)	0.99434 (10)	0.10831 (4)	0.0209 (2)
H8B	0.1022	1.0483	0.0818	0.031*
O9	0.00284 (10)	1.09961 (10)	0.15130 (4)	0.0226 (2)
C15	0.13464 (15)	0.84945 (15)	0.30203 (6)	0.0243 (3)
H15A	0.1073	0.8584	0.3357	0.029*
C16	0.22228 (14)	0.75286 (15)	0.30017 (7)	0.0258 (3)
H16A	0.2539	0.6973	0.3328	0.031*
C17	0.26428 (14)	0.73742 (15)	0.24987 (7)	0.0238 (3)
H17A	0.3225	0.6712	0.2486	0.029*
C18	0.21830 (13)	0.82174 (14)	0.20201 (6)	0.0193 (3)
H18A	0.2467	0.8124	0.1686	0.023*
C19	0.12974 (12)	0.92108 (13)	0.20291 (6)	0.0161 (3)
C20	0.08674 (13)	0.93391 (14)	0.25345 (6)	0.0182 (3)
C21	0.08283 (12)	1.01232 (13)	0.15196 (6)	0.0170 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0346 (6)	0.0406 (7)	0.0266 (5)	0.0103 (5)	0.0144 (5)	0.0040 (5)
O2	0.0233 (5)	0.0252 (5)	0.0210 (5)	0.0045 (4)	0.0110 (4)	0.0023 (4)
O3	0.0221 (5)	0.0234 (5)	0.0204 (5)	0.0038 (4)	0.0081 (4)	0.0015 (4)
C1	0.0284 (8)	0.0248 (8)	0.0379 (9)	0.0063 (6)	0.0070 (7)	0.0024 (6)
C2	0.0219 (7)	0.0259 (8)	0.0389 (9)	0.0027 (6)	0.0085 (6)	−0.0100 (6)
C3	0.0223 (7)	0.0301 (8)	0.0268 (7)	−0.0025 (6)	0.0103 (6)	−0.0099 (6)
C4	0.0198 (6)	0.0216 (7)	0.0199 (6)	−0.0024 (5)	0.0047 (5)	−0.0045 (5)
C5	0.0177 (6)	0.0183 (6)	0.0210 (6)	−0.0020 (5)	0.0058 (5)	−0.0039 (5)
C6	0.0250 (7)	0.0234 (7)	0.0279 (7)	0.0016 (6)	0.0081 (6)	0.0018 (6)
C7	0.0173 (6)	0.0192 (6)	0.0188 (6)	−0.0034 (5)	0.0052 (5)	−0.0031 (5)
O4	0.0315 (6)	0.0307 (6)	0.0236 (5)	0.0018 (5)	0.0063 (4)	−0.0038 (4)
O5	0.0272 (5)	0.0261 (6)	0.0307 (6)	−0.0055 (5)	0.0092 (4)	0.0005 (4)
O6	0.0258 (5)	0.0320 (6)	0.0235 (5)	−0.0064 (4)	0.0149 (4)	0.0004 (4)
C8	0.0177 (6)	0.0276 (8)	0.0283 (7)	0.0040 (6)	0.0083 (5)	0.0080 (6)
C9	0.0233 (7)	0.0367 (9)	0.0288 (7)	0.0096 (6)	0.0156 (6)	0.0135 (6)
C10	0.0307 (8)	0.0361 (9)	0.0196 (7)	0.0123 (7)	0.0123 (6)	0.0061 (6)
C11	0.0229 (7)	0.0225 (7)	0.0209 (6)	0.0081 (6)	0.0059 (5)	0.0021 (5)
C12	0.0202 (6)	0.0193 (7)	0.0187 (6)	0.0060 (5)	0.0082 (5)	0.0048 (5)
C13	0.0200 (6)	0.0219 (7)	0.0194 (6)	0.0046 (5)	0.0069 (5)	0.0051 (5)
C14	0.0196 (6)	0.0189 (6)	0.0219 (6)	0.0031 (5)	0.0072 (5)	0.0047 (5)
N1	0.0242 (6)	0.0239 (6)	0.0162 (5)	0.0061 (5)	0.0101 (4)	0.0050 (4)
N2	0.0218 (5)	0.0202 (6)	0.0172 (5)	0.0020 (5)	0.0074 (4)	0.0020 (4)
N3	0.0220 (6)	0.0245 (6)	0.0181 (5)	0.0007 (5)	0.0096 (4)	−0.0012 (4)
N4	0.0188 (5)	0.0209 (6)	0.0183 (5)	0.0004 (5)	0.0052 (4)	0.0019 (4)
N5	0.0215 (6)	0.0271 (6)	0.0128 (5)	−0.0049 (5)	0.0075 (4)	−0.0006 (4)
C22	0.0174 (6)	0.0189 (6)	0.0157 (6)	−0.0017 (5)	0.0048 (5)	−0.0007 (5)
C23	0.0229 (7)	0.0232 (7)	0.0205 (6)	0.0025 (6)	0.0081 (5)	0.0008 (5)
C24	0.0173 (6)	0.0208 (7)	0.0149 (6)	−0.0048 (5)	0.0051 (5)	−0.0019 (5)
C25	0.0177 (6)	0.0198 (6)	0.0138 (6)	−0.0024 (5)	0.0054 (5)	−0.0006 (5)
C26	0.0201 (6)	0.0238 (7)	0.0174 (6)	−0.0022 (6)	0.0029 (5)	0.0031 (5)
O7	0.0308 (5)	0.0222 (5)	0.0178 (5)	0.0063 (4)	0.0114 (4)	0.0022 (4)
O8	0.0247 (5)	0.0238 (5)	0.0165 (4)	0.0076 (4)	0.0094 (4)	0.0052 (4)
O9	0.0278 (5)	0.0235 (5)	0.0190 (5)	0.0097 (4)	0.0107 (4)	0.0047 (4)
C15	0.0324 (7)	0.0245 (7)	0.0169 (6)	−0.0010 (6)	0.0086 (6)	0.0034 (5)
C16	0.0290 (7)	0.0239 (7)	0.0215 (7)	−0.0003 (6)	0.0025 (6)	0.0089 (5)
C17	0.0208 (6)	0.0202 (7)	0.0288 (7)	0.0025 (6)	0.0048 (5)	0.0045 (6)
C18	0.0181 (6)	0.0192 (7)	0.0211 (6)	−0.0005 (5)	0.0065 (5)	0.0009 (5)
C19	0.0164 (6)	0.0162 (6)	0.0152 (6)	−0.0015 (5)	0.0037 (5)	0.0006 (5)
C20	0.0204 (6)	0.0169 (6)	0.0176 (6)	−0.0019 (5)	0.0059 (5)	−0.0010 (5)
C21	0.0180 (6)	0.0177 (6)	0.0157 (6)	−0.0009 (5)	0.0055 (5)	−0.0005 (5)

Geometric parameters (Å, º) top

O1—C4	1.3411 (18)	N1—C22	1.3247 (17)
O1—H1D	0.8201	N1—H1A	0.8601
O2—C7	1.3128 (17)	N1—H1B	0.8599
O2—H2C	0.8200	N2—C23	1.3411 (18)
O3—C7	1.2381 (17)	N2—C22	1.3572 (18)
C1—C6	1.383 (2)	N3—C23	1.3241 (18)
C1—C2	1.398 (2)	N3—C24	1.3476 (19)
C1—H1C	0.9300	N4—C26	1.3169 (18)
C2—C3	1.375 (2)	N4—C25	1.3854 (18)
C2—H2B	0.9300	N5—C26	1.3571 (19)
C3—C4	1.395 (2)	N5—C24	1.3642 (18)
C3—H3B	0.9300	N5—H5A	0.8601
C4—C5	1.4110 (19)	C22—C25	1.4155 (18)
C5—C6	1.402 (2)	C23—H23A	0.9300
C5—C7	1.4756 (19)	C24—C25	1.3916 (18)
C6—H6A	0.9300	C26—H26A	0.9300
O4—C11	1.3568 (19)	O7—C20	1.3600 (17)
O4—H4B	0.8199	O7—H7A	0.8201
O5—C14	1.2289 (18)	O8—C21	1.3082 (16)
O6—C14	1.3146 (17)	O8—H8B	0.8200
O6—H6B	0.8203	O9—C21	1.2394 (17)
C8—C13	1.381 (2)	C15—C16	1.378 (2)
C8—C9	1.397 (2)	C15—C20	1.3964 (19)
C8—H8A	0.9300	C15—H15A	0.9300
C9—C10	1.380 (2)	C16—C17	1.397 (2)
C9—H9A	0.9300	C16—H16A	0.9300
C10—C11	1.401 (2)	C17—C18	1.381 (2)
C10—H10A	0.9300	C17—H17A	0.9300
C11—C12	1.4059 (19)	C18—C19	1.3995 (19)
C12—C13	1.400 (2)	C18—H18A	0.9300
C12—C14	1.4803 (19)	C19—C20	1.4062 (18)
C13—H13A	0.9300	C19—C21	1.4762 (18)

C4—O1—H1D	109.5	C22—N1—H1B	120.1
C7—O2—H2C	109.5	H1A—N1—H1B	120.0
C6—C1—C2	119.24 (15)	C23—N2—C22	119.92 (12)
C6—C1—H1C	120.4	C23—N3—C24	112.09 (12)
C2—C1—H1C	120.4	C26—N4—C25	104.22 (11)
C3—C2—C1	120.96 (14)	C26—N5—C24	106.84 (11)
C3—C2—H2B	119.5	C26—N5—H5A	126.6
C1—C2—H2B	119.5	C24—N5—H5A	126.6
C2—C3—C4	120.26 (14)	N1—C22—N2	118.36 (12)
C2—C3—H3B	119.9	N1—C22—C25	124.68 (13)
C4—C3—H3B	119.9	N2—C22—C25	116.96 (12)
O1—C4—C3	117.27 (13)	N3—C23—N2	127.88 (13)
O1—C4—C5	123.15 (13)	N3—C23—H23A	116.1
C3—C4—C5	119.58 (14)	N2—C23—H23A	116.1
C6—C5—C4	119.08 (13)	N3—C24—N5	128.14 (12)
C6—C5—C7	121.60 (13)	N3—C24—C25	126.21 (12)
C4—C5—C7	119.32 (13)	N5—C24—C25	105.65 (12)
C1—C6—C5	120.86 (15)	N4—C25—C24	110.01 (11)
C1—C6—H6A	119.6	N4—C25—C22	133.06 (12)
C5—C6—H6A	119.6	C24—C25—C22	116.93 (12)
O3—C7—O2	122.51 (13)	N4—C26—N5	113.29 (12)
O3—C7—C5	122.02 (12)	N4—C26—H26A	123.4
O2—C7—C5	115.47 (12)	N5—C26—H26A	123.4
C11—O4—H4B	109.5	C20—O7—H7A	109.5
C14—O6—H6B	109.5	C21—O8—H8B	109.5
C13—C8—C9	119.17 (15)	C16—C15—C20	120.21 (13)
C13—C8—H8A	120.4	C16—C15—H15A	119.9
C9—C8—H8A	120.4	C20—C15—H15A	119.9
C10—C9—C8	121.02 (14)	C15—C16—C17	120.81 (13)
C10—C9—H9A	119.5	C15—C16—H16A	119.6
C8—C9—H9A	119.5	C17—C16—H16A	119.6
C9—C10—C11	119.96 (14)	C18—C17—C16	119.17 (14)
C9—C10—H10A	120.0	C18—C17—H17A	120.4
C11—C10—H10A	120.0	C16—C17—H17A	120.4
O4—C11—C10	118.31 (13)	C17—C18—C19	121.12 (13)
O4—C11—C12	122.16 (13)	C17—C18—H18A	119.4
C10—C11—C12	119.52 (14)	C19—C18—H18A	119.4
C13—C12—C11	119.32 (13)	C18—C19—C20	119.04 (12)
C13—C12—C14	121.21 (12)	C18—C19—C21	120.74 (12)
C11—C12—C14	119.45 (13)	C20—C19—C21	120.22 (12)
C8—C13—C12	120.99 (13)	O7—C20—C15	117.65 (12)
C8—C13—H13A	119.5	O7—C20—C19	122.71 (12)
C12—C13—H13A	119.5	C15—C20—C19	119.64 (13)
O5—C14—O6	122.80 (13)	O9—C21—O8	123.07 (12)
O5—C14—C12	123.13 (13)	O9—C21—C19	121.93 (12)
O6—C14—C12	114.06 (12)	O8—C21—C19	114.99 (12)
C22—N1—H1A	119.9

C6—C1—C2—C3	−0.1 (2)	C22—N2—C23—N3	0.3 (2)
C1—C2—C3—C4	0.7 (2)	C23—N3—C24—N5	179.88 (13)
C2—C3—C4—O1	179.11 (14)	C23—N3—C24—C25	−0.5 (2)
C2—C3—C4—C5	−0.9 (2)	C26—N5—C24—N3	179.76 (13)
O1—C4—C5—C6	−179.48 (13)	C26—N5—C24—C25	0.09 (14)
C3—C4—C5—C6	0.5 (2)	C26—N4—C25—C24	−0.25 (15)
O1—C4—C5—C7	−0.1 (2)	C26—N4—C25—C22	179.27 (15)
C3—C4—C5—C7	179.94 (12)	N3—C24—C25—N4	−179.58 (12)
C2—C1—C6—C5	−0.3 (2)	N5—C24—C25—N4	0.10 (15)
C4—C5—C6—C1	0.1 (2)	N3—C24—C25—C22	0.8 (2)
C7—C5—C6—C1	−179.32 (14)	N5—C24—C25—C22	−179.51 (11)
C6—C5—C7—O3	177.52 (13)	N1—C22—C25—N4	−0.4 (2)
C4—C5—C7—O3	−1.9 (2)	N2—C22—C25—N4	180.00 (13)
C6—C5—C7—O2	−2.09 (19)	N1—C22—C25—C24	179.08 (13)
C4—C5—C7—O2	178.54 (12)	N2—C22—C25—C24	−0.50 (18)
C13—C8—C9—C10	−0.8 (2)	C25—N4—C26—N5	0.31 (15)
C8—C9—C10—C11	0.0 (2)	C24—N5—C26—N4	−0.26 (16)
C9—C10—C11—O4	179.69 (13)	C20—C15—C16—C17	−0.2 (2)
C9—C10—C11—C12	1.1 (2)	C15—C16—C17—C18	1.0 (2)
O4—C11—C12—C13	−179.95 (13)	C16—C17—C18—C19	−0.6 (2)
C10—C11—C12—C13	−1.4 (2)	C17—C18—C19—C20	−0.4 (2)
O4—C11—C12—C14	−1.3 (2)	C17—C18—C19—C21	178.90 (13)
C10—C11—C12—C14	177.17 (13)	C16—C15—C20—O7	179.13 (13)
C9—C8—C13—C12	0.5 (2)	C16—C15—C20—C19	−0.9 (2)
C11—C12—C13—C8	0.6 (2)	C18—C19—C20—O7	−178.81 (12)
C14—C12—C13—C8	−177.94 (13)	C21—C19—C20—O7	1.8 (2)
C13—C12—C14—O5	−172.14 (13)	C18—C19—C20—C15	1.2 (2)
C11—C12—C14—O5	9.3 (2)	C21—C19—C20—C15	−178.15 (13)
C13—C12—C14—O6	8.60 (19)	C18—C19—C21—O9	178.77 (13)
C11—C12—C14—O6	−169.98 (12)	C20—C19—C21—O9	−1.9 (2)
C23—N2—C22—N1	−179.60 (13)	C18—C19—C21—O8	−1.68 (18)
C23—N2—C22—C25	0.01 (19)	C20—C19—C21—O8	177.67 (12)
C24—N3—C23—N2	−0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···O3	0.82	1.87	2.5946 (17)	146
O4—H4B···O5	0.82	1.89	2.6111 (18)	146
O7—H7A···O9	0.82	1.89	2.6118 (15)	146
O2—H2C···N4ⁱ	0.82	1.87	2.6795 (18)	167
O6—H6B···N3ⁱⁱ	0.82	1.82	2.6305 (18)	172
O8—H8B···N2ⁱⁱⁱ	0.82	1.78	2.5864 (17)	168
N1—H1A···O9ⁱⁱⁱ	0.86	2.09	2.9302 (17)	167
N1—H1B···O3ⁱ	0.86	2.01	2.8593 (18)	171
N5—H5A···O7ⁱⁱ	0.86	2.14	2.8585 (17)	141

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

Experimental details

Crystal data
Chemical formula	3C₇H₆O₃·C₅H₅N₅
M_r	549.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.998 (2), 10.053 (2), 23.490 (7)
β (°)	106.98 (3)
V (Å³)	2483.9 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.38 × 0.22 × 0.14

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22329, 5680, 4872
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.116, 1.06
No. of reflections	5680
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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—H1D···O3	0.82	1.87	2.5946 (17)	146
O4—H4B···O5	0.82	1.89	2.6111 (18)	146
O7—H7A···O9	0.82	1.89	2.6118 (15)	146
O2—H2C···N4ⁱ	0.82	1.87	2.6795 (18)	167
O6—H6B···N3ⁱⁱ	0.82	1.82	2.6305 (18)	172
O8—H8B···N2ⁱⁱⁱ	0.82	1.78	2.5864 (17)	168
N1—H1A···O9ⁱⁱⁱ	0.86	2.09	2.9302 (17)	167
N1—H1B···O3ⁱ	0.86	2.01	2.8593 (18)	171
N5—H5A···O7ⁱⁱ	0.86	2.14	2.8585 (17)	141

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

References

Forsythe, P. & Ennis, M. (1999). Inflam. Res. 48, 301–307. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 65| Part 8| August 2009| Page o1791

doi:10.1107/S1600536809025240

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