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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Forsythe, P. & Ennis, M. (1999). Inflam. Res. 48, 301-307.]).

[Scheme 1]

Experimental

Crystal data
  • 3C7H6O3·C5H5N5

  • Mr = 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)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.116

  • S = 1.06

  • 5680 reflections

  • 361 parameters

  • H-atom parameters constrained

  • Δρmax = 0.83 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

The H atoms were located geometrically (C—H = 0.93–0.97 Å, N—H = 0.86Å, O—H = 0.82Å) and refined as riding with Uiso(H) = 1.2 Ueq(carrier). The highest difference peak is 0.45Å from H6A and might indicate unmodelled positional disorder of O1.

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
[Figure 1] 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·C5H5N5F(000) = 1144
Mr = 549.49Dx = 1.469 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5680 reflections
a = 10.998 (2) Åθ = 3.0–27.5°
b = 10.053 (2) ŵ = 0.11 mm1
c = 23.490 (7) ÅT = 293 K
β = 106.98 (3)°Block, colourless
V = 2483.9 (10) Å30.38 × 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 tubeRint = 0.020
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
ω scansh = 1414
22329 measured reflectionsk = 1312
5680 independent reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0624P)2 + 1.1319P]
where P = (Fo2 + 2Fc2)/3
5680 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.83 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
3C7H6O3·C5H5N5V = 2483.9 (10) Å3
Mr = 549.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.998 (2) ŵ = 0.11 mm1
b = 10.053 (2) ÅT = 293 K
c = 23.490 (7) Å0.38 × 0.22 × 0.14 mm
β = 106.98 (3)°
Data collection top
Siemens SMART CCD
diffractometer
4872 reflections with I > 2σ(I)
22329 measured reflectionsRint = 0.020
5680 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.06Δρmax = 0.83 e Å3
5680 reflectionsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
O10.58987 (11)0.54268 (12)0.10882 (5)0.0328 (3)
H1D0.64640.50350.09930.049*
O20.70858 (10)0.59642 (10)0.04308 (4)0.0222 (2)
H2C0.76630.54680.04510.033*
O30.73581 (9)0.48786 (10)0.04287 (4)0.0216 (2)
C10.42191 (15)0.83244 (16)0.01407 (8)0.0309 (3)
H1C0.38320.89860.04100.037*
C20.38415 (14)0.81020 (16)0.03701 (7)0.0290 (3)
H2B0.32000.86210.04400.035*
C30.44049 (14)0.71264 (16)0.07710 (7)0.0258 (3)
H3B0.41360.69850.11060.031*
C40.53780 (13)0.63482 (14)0.06763 (6)0.0207 (3)
C50.57687 (13)0.65547 (14)0.01619 (6)0.0190 (3)
C60.51750 (14)0.75499 (15)0.02417 (7)0.0254 (3)
H6A0.54270.76910.05820.030*
C70.67994 (13)0.57290 (14)0.00646 (6)0.0184 (3)
O40.24665 (11)0.29192 (11)0.20033 (5)0.0290 (2)
H4B0.20490.26500.22170.043*
O50.18452 (10)0.26468 (11)0.29882 (5)0.0279 (2)
O60.27892 (10)0.39746 (11)0.37517 (4)0.0254 (2)
H6B0.22550.36460.38910.038*
C80.54365 (13)0.53292 (16)0.29552 (7)0.0242 (3)
H8A0.61110.58620.31640.029*
C90.52558 (14)0.50464 (17)0.23539 (7)0.0279 (3)
H9A0.58090.54050.21620.033*
C100.42685 (15)0.42432 (17)0.20407 (7)0.0277 (3)
H10A0.41610.40640.16410.033*
C110.34292 (13)0.36986 (15)0.23260 (6)0.0222 (3)
C120.35880 (13)0.39957 (14)0.29283 (6)0.0189 (3)
C130.46011 (13)0.48074 (14)0.32360 (6)0.0202 (3)
H13A0.47130.49980.36350.024*
C140.26650 (13)0.34705 (14)0.32213 (6)0.0199 (3)
N10.08652 (11)0.72297 (12)0.04856 (5)0.0205 (2)
H1A0.07190.77250.07970.025*
H1B0.14240.66070.04290.025*
N20.06434 (11)0.84210 (12)0.01967 (5)0.0193 (2)
N30.12090 (11)0.80213 (12)0.06983 (5)0.0208 (2)
N40.11815 (11)0.56210 (12)0.06827 (5)0.0194 (2)
N50.00044 (11)0.61900 (12)0.12747 (5)0.0200 (2)
H5A0.02960.61760.15740.024*
C220.02299 (12)0.74279 (14)0.00930 (6)0.0173 (3)
C230.12982 (13)0.86541 (15)0.01934 (6)0.0218 (3)
H23A0.18860.93440.00980.026*
C240.03382 (12)0.70387 (14)0.08015 (6)0.0176 (3)
C250.03992 (12)0.66798 (14)0.04351 (5)0.0169 (3)
C260.09105 (13)0.53725 (15)0.11826 (6)0.0210 (3)
H26A0.13010.47030.14460.025*
O70.00080 (10)1.02622 (10)0.25745 (4)0.0227 (2)
H7A0.02141.07090.22690.034*
O80.13258 (9)0.99434 (10)0.10831 (4)0.0209 (2)
H8B0.10221.04830.08180.031*
O90.00284 (10)1.09961 (10)0.15130 (4)0.0226 (2)
C150.13464 (15)0.84945 (15)0.30203 (6)0.0243 (3)
H15A0.10730.85840.33570.029*
C160.22228 (14)0.75286 (15)0.30017 (7)0.0258 (3)
H16A0.25390.69730.33280.031*
C170.26428 (14)0.73742 (15)0.24987 (7)0.0238 (3)
H17A0.32250.67120.24860.029*
C180.21830 (13)0.82174 (14)0.20201 (6)0.0193 (3)
H18A0.24670.81240.16860.023*
C190.12974 (12)0.92108 (13)0.20291 (6)0.0161 (3)
C200.08674 (13)0.93391 (14)0.25345 (6)0.0182 (3)
C210.08283 (12)1.01232 (13)0.15196 (6)0.0170 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0346 (6)0.0406 (7)0.0266 (5)0.0103 (5)0.0144 (5)0.0040 (5)
O20.0233 (5)0.0252 (5)0.0210 (5)0.0045 (4)0.0110 (4)0.0023 (4)
O30.0221 (5)0.0234 (5)0.0204 (5)0.0038 (4)0.0081 (4)0.0015 (4)
C10.0284 (8)0.0248 (8)0.0379 (9)0.0063 (6)0.0070 (7)0.0024 (6)
C20.0219 (7)0.0259 (8)0.0389 (9)0.0027 (6)0.0085 (6)0.0100 (6)
C30.0223 (7)0.0301 (8)0.0268 (7)0.0025 (6)0.0103 (6)0.0099 (6)
C40.0198 (6)0.0216 (7)0.0199 (6)0.0024 (5)0.0047 (5)0.0045 (5)
C50.0177 (6)0.0183 (6)0.0210 (6)0.0020 (5)0.0058 (5)0.0039 (5)
C60.0250 (7)0.0234 (7)0.0279 (7)0.0016 (6)0.0081 (6)0.0018 (6)
C70.0173 (6)0.0192 (6)0.0188 (6)0.0034 (5)0.0052 (5)0.0031 (5)
O40.0315 (6)0.0307 (6)0.0236 (5)0.0018 (5)0.0063 (4)0.0038 (4)
O50.0272 (5)0.0261 (6)0.0307 (6)0.0055 (5)0.0092 (4)0.0005 (4)
O60.0258 (5)0.0320 (6)0.0235 (5)0.0064 (4)0.0149 (4)0.0004 (4)
C80.0177 (6)0.0276 (8)0.0283 (7)0.0040 (6)0.0083 (5)0.0080 (6)
C90.0233 (7)0.0367 (9)0.0288 (7)0.0096 (6)0.0156 (6)0.0135 (6)
C100.0307 (8)0.0361 (9)0.0196 (7)0.0123 (7)0.0123 (6)0.0061 (6)
C110.0229 (7)0.0225 (7)0.0209 (6)0.0081 (6)0.0059 (5)0.0021 (5)
C120.0202 (6)0.0193 (7)0.0187 (6)0.0060 (5)0.0082 (5)0.0048 (5)
C130.0200 (6)0.0219 (7)0.0194 (6)0.0046 (5)0.0069 (5)0.0051 (5)
C140.0196 (6)0.0189 (6)0.0219 (6)0.0031 (5)0.0072 (5)0.0047 (5)
N10.0242 (6)0.0239 (6)0.0162 (5)0.0061 (5)0.0101 (4)0.0050 (4)
N20.0218 (5)0.0202 (6)0.0172 (5)0.0020 (5)0.0074 (4)0.0020 (4)
N30.0220 (6)0.0245 (6)0.0181 (5)0.0007 (5)0.0096 (4)0.0012 (4)
N40.0188 (5)0.0209 (6)0.0183 (5)0.0004 (5)0.0052 (4)0.0019 (4)
N50.0215 (6)0.0271 (6)0.0128 (5)0.0049 (5)0.0075 (4)0.0006 (4)
C220.0174 (6)0.0189 (6)0.0157 (6)0.0017 (5)0.0048 (5)0.0007 (5)
C230.0229 (7)0.0232 (7)0.0205 (6)0.0025 (6)0.0081 (5)0.0008 (5)
C240.0173 (6)0.0208 (7)0.0149 (6)0.0048 (5)0.0051 (5)0.0019 (5)
C250.0177 (6)0.0198 (6)0.0138 (6)0.0024 (5)0.0054 (5)0.0006 (5)
C260.0201 (6)0.0238 (7)0.0174 (6)0.0022 (6)0.0029 (5)0.0031 (5)
O70.0308 (5)0.0222 (5)0.0178 (5)0.0063 (4)0.0114 (4)0.0022 (4)
O80.0247 (5)0.0238 (5)0.0165 (4)0.0076 (4)0.0094 (4)0.0052 (4)
O90.0278 (5)0.0235 (5)0.0190 (5)0.0097 (4)0.0107 (4)0.0047 (4)
C150.0324 (7)0.0245 (7)0.0169 (6)0.0010 (6)0.0086 (6)0.0034 (5)
C160.0290 (7)0.0239 (7)0.0215 (7)0.0003 (6)0.0025 (6)0.0089 (5)
C170.0208 (6)0.0202 (7)0.0288 (7)0.0025 (6)0.0048 (5)0.0045 (6)
C180.0181 (6)0.0192 (7)0.0211 (6)0.0005 (5)0.0065 (5)0.0009 (5)
C190.0164 (6)0.0162 (6)0.0152 (6)0.0015 (5)0.0037 (5)0.0006 (5)
C200.0204 (6)0.0169 (6)0.0176 (6)0.0019 (5)0.0059 (5)0.0010 (5)
C210.0180 (6)0.0177 (6)0.0157 (6)0.0009 (5)0.0055 (5)0.0005 (5)
Geometric parameters (Å, º) top
O1—C41.3411 (18)N1—C221.3247 (17)
O1—H1D0.8201N1—H1A0.8601
O2—C71.3128 (17)N1—H1B0.8599
O2—H2C0.8200N2—C231.3411 (18)
O3—C71.2381 (17)N2—C221.3572 (18)
C1—C61.383 (2)N3—C231.3241 (18)
C1—C21.398 (2)N3—C241.3476 (19)
C1—H1C0.9300N4—C261.3169 (18)
C2—C31.375 (2)N4—C251.3854 (18)
C2—H2B0.9300N5—C261.3571 (19)
C3—C41.395 (2)N5—C241.3642 (18)
C3—H3B0.9300N5—H5A0.8601
C4—C51.4110 (19)C22—C251.4155 (18)
C5—C61.402 (2)C23—H23A0.9300
C5—C71.4756 (19)C24—C251.3916 (18)
C6—H6A0.9300C26—H26A0.9300
O4—C111.3568 (19)O7—C201.3600 (17)
O4—H4B0.8199O7—H7A0.8201
O5—C141.2289 (18)O8—C211.3082 (16)
O6—C141.3146 (17)O8—H8B0.8200
O6—H6B0.8203O9—C211.2394 (17)
C8—C131.381 (2)C15—C161.378 (2)
C8—C91.397 (2)C15—C201.3964 (19)
C8—H8A0.9300C15—H15A0.9300
C9—C101.380 (2)C16—C171.397 (2)
C9—H9A0.9300C16—H16A0.9300
C10—C111.401 (2)C17—C181.381 (2)
C10—H10A0.9300C17—H17A0.9300
C11—C121.4059 (19)C18—C191.3995 (19)
C12—C131.400 (2)C18—H18A0.9300
C12—C141.4803 (19)C19—C201.4062 (18)
C13—H13A0.9300C19—C211.4762 (18)
C4—O1—H1D109.5C22—N1—H1B120.1
C7—O2—H2C109.5H1A—N1—H1B120.0
C6—C1—C2119.24 (15)C23—N2—C22119.92 (12)
C6—C1—H1C120.4C23—N3—C24112.09 (12)
C2—C1—H1C120.4C26—N4—C25104.22 (11)
C3—C2—C1120.96 (14)C26—N5—C24106.84 (11)
C3—C2—H2B119.5C26—N5—H5A126.6
C1—C2—H2B119.5C24—N5—H5A126.6
C2—C3—C4120.26 (14)N1—C22—N2118.36 (12)
C2—C3—H3B119.9N1—C22—C25124.68 (13)
C4—C3—H3B119.9N2—C22—C25116.96 (12)
O1—C4—C3117.27 (13)N3—C23—N2127.88 (13)
O1—C4—C5123.15 (13)N3—C23—H23A116.1
C3—C4—C5119.58 (14)N2—C23—H23A116.1
C6—C5—C4119.08 (13)N3—C24—N5128.14 (12)
C6—C5—C7121.60 (13)N3—C24—C25126.21 (12)
C4—C5—C7119.32 (13)N5—C24—C25105.65 (12)
C1—C6—C5120.86 (15)N4—C25—C24110.01 (11)
C1—C6—H6A119.6N4—C25—C22133.06 (12)
C5—C6—H6A119.6C24—C25—C22116.93 (12)
O3—C7—O2122.51 (13)N4—C26—N5113.29 (12)
O3—C7—C5122.02 (12)N4—C26—H26A123.4
O2—C7—C5115.47 (12)N5—C26—H26A123.4
C11—O4—H4B109.5C20—O7—H7A109.5
C14—O6—H6B109.5C21—O8—H8B109.5
C13—C8—C9119.17 (15)C16—C15—C20120.21 (13)
C13—C8—H8A120.4C16—C15—H15A119.9
C9—C8—H8A120.4C20—C15—H15A119.9
C10—C9—C8121.02 (14)C15—C16—C17120.81 (13)
C10—C9—H9A119.5C15—C16—H16A119.6
C8—C9—H9A119.5C17—C16—H16A119.6
C9—C10—C11119.96 (14)C18—C17—C16119.17 (14)
C9—C10—H10A120.0C18—C17—H17A120.4
C11—C10—H10A120.0C16—C17—H17A120.4
O4—C11—C10118.31 (13)C17—C18—C19121.12 (13)
O4—C11—C12122.16 (13)C17—C18—H18A119.4
C10—C11—C12119.52 (14)C19—C18—H18A119.4
C13—C12—C11119.32 (13)C18—C19—C20119.04 (12)
C13—C12—C14121.21 (12)C18—C19—C21120.74 (12)
C11—C12—C14119.45 (13)C20—C19—C21120.22 (12)
C8—C13—C12120.99 (13)O7—C20—C15117.65 (12)
C8—C13—H13A119.5O7—C20—C19122.71 (12)
C12—C13—H13A119.5C15—C20—C19119.64 (13)
O5—C14—O6122.80 (13)O9—C21—O8123.07 (12)
O5—C14—C12123.13 (13)O9—C21—C19121.93 (12)
O6—C14—C12114.06 (12)O8—C21—C19114.99 (12)
C22—N1—H1A119.9
C6—C1—C2—C30.1 (2)C22—N2—C23—N30.3 (2)
C1—C2—C3—C40.7 (2)C23—N3—C24—N5179.88 (13)
C2—C3—C4—O1179.11 (14)C23—N3—C24—C250.5 (2)
C2—C3—C4—C50.9 (2)C26—N5—C24—N3179.76 (13)
O1—C4—C5—C6179.48 (13)C26—N5—C24—C250.09 (14)
C3—C4—C5—C60.5 (2)C26—N4—C25—C240.25 (15)
O1—C4—C5—C70.1 (2)C26—N4—C25—C22179.27 (15)
C3—C4—C5—C7179.94 (12)N3—C24—C25—N4179.58 (12)
C2—C1—C6—C50.3 (2)N5—C24—C25—N40.10 (15)
C4—C5—C6—C10.1 (2)N3—C24—C25—C220.8 (2)
C7—C5—C6—C1179.32 (14)N5—C24—C25—C22179.51 (11)
C6—C5—C7—O3177.52 (13)N1—C22—C25—N40.4 (2)
C4—C5—C7—O31.9 (2)N2—C22—C25—N4180.00 (13)
C6—C5—C7—O22.09 (19)N1—C22—C25—C24179.08 (13)
C4—C5—C7—O2178.54 (12)N2—C22—C25—C240.50 (18)
C13—C8—C9—C100.8 (2)C25—N4—C26—N50.31 (15)
C8—C9—C10—C110.0 (2)C24—N5—C26—N40.26 (16)
C9—C10—C11—O4179.69 (13)C20—C15—C16—C170.2 (2)
C9—C10—C11—C121.1 (2)C15—C16—C17—C181.0 (2)
O4—C11—C12—C13179.95 (13)C16—C17—C18—C190.6 (2)
C10—C11—C12—C131.4 (2)C17—C18—C19—C200.4 (2)
O4—C11—C12—C141.3 (2)C17—C18—C19—C21178.90 (13)
C10—C11—C12—C14177.17 (13)C16—C15—C20—O7179.13 (13)
C9—C8—C13—C120.5 (2)C16—C15—C20—C190.9 (2)
C11—C12—C13—C80.6 (2)C18—C19—C20—O7178.81 (12)
C14—C12—C13—C8177.94 (13)C21—C19—C20—O71.8 (2)
C13—C12—C14—O5172.14 (13)C18—C19—C20—C151.2 (2)
C11—C12—C14—O59.3 (2)C21—C19—C20—C15178.15 (13)
C13—C12—C14—O68.60 (19)C18—C19—C21—O9178.77 (13)
C11—C12—C14—O6169.98 (12)C20—C19—C21—O91.9 (2)
C23—N2—C22—N1179.60 (13)C18—C19—C21—O81.68 (18)
C23—N2—C22—C250.01 (19)C20—C19—C21—O8177.67 (12)
C24—N3—C23—N20.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1D···O30.821.872.5946 (17)146
O4—H4B···O50.821.892.6111 (18)146
O7—H7A···O90.821.892.6118 (15)146
O2—H2C···N4i0.821.872.6795 (18)167
O6—H6B···N3ii0.821.822.6305 (18)172
O8—H8B···N2iii0.821.782.5864 (17)168
N1—H1A···O9iii0.862.092.9302 (17)167
N1—H1B···O3i0.862.012.8593 (18)171
N5—H5A···O7ii0.862.142.8585 (17)141
Symmetry codes: (i) x+1, y+1, z; (ii) x, y1/2, z+1/2; (iii) x, y+2, z.

Experimental details

Crystal data
Chemical formula3C7H6O3·C5H5N5
Mr549.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.998 (2), 10.053 (2), 23.490 (7)
β (°) 106.98 (3)
V3)2483.9 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.38 × 0.22 × 0.14
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
22329, 5680, 4872
Rint0.020
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.116, 1.06
No. of reflections5680
No. of parameters361
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1D···O30.821.872.5946 (17)146
O4—H4B···O50.821.892.6111 (18)146
O7—H7A···O90.821.892.6118 (15)146
O2—H2C···N4i0.821.872.6795 (18)167
O6—H6B···N3ii0.821.822.6305 (18)172
O8—H8B···N2iii0.821.782.5864 (17)168
N1—H1A···O9iii0.862.092.9302 (17)167
N1—H1B···O3i0.862.012.8593 (18)171
N5—H5A···O7ii0.862.142.8585 (17)141
Symmetry codes: (i) x+1, y+1, z; (ii) x, y1/2, z+1/2; (iii) x, y+2, z.
 

References

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds