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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1791.
Published online 2009 July 8. doi:  10.1107/S1600536809025240
PMCID: PMC2977431

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

Abstract

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 [triangle]).

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Object name is e-65-o1791-scheme1.jpg

Experimental

Crystal data

  • 3C7H6O3·C5H5N5
  • M r = 549.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1791-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 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

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025240/hb5001sup1.cif

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

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.
The molecular structure of (I), drawn with 30% probability ellipsoids.

Crystal data

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

Siemens SMART CCD diffractometer4872 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
graphiteθmax = 27.5°, θmin = 3.0°
ω scansh = −14→14
22329 measured reflectionsk = −13→12
5680 independent reflectionsl = −30→30

Refinement

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 = 1.06w = 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

Special details

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)

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)
H2C0.76630.5468−0.04510.033*
O30.73581 (9)0.48786 (10)0.04287 (4)0.0216 (2)
C10.42191 (15)0.83244 (16)−0.01407 (8)0.0309 (3)
H1C0.38320.8986−0.04100.037*
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)
H6A0.54270.7691−0.05820.030*
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)
H1A0.07190.7725−0.07970.025*
H1B0.14240.6607−0.04290.025*
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)
N40.11815 (11)0.56210 (12)0.06827 (5)0.0194 (2)
N50.00044 (11)0.61900 (12)0.12747 (5)0.0200 (2)
H5A−0.02960.61760.15740.024*
C220.02299 (12)0.74279 (14)−0.00930 (6)0.0173 (3)
C23−0.12982 (13)0.86541 (15)0.01934 (6)0.0218 (3)
H23A−0.18860.93440.00980.026*
C24−0.03382 (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*
O7−0.00080 (10)1.02622 (10)0.25745 (4)0.0227 (2)
H7A−0.02141.07090.22690.034*
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)

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, °)

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—C3−0.1 (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—C25−0.5 (2)
C2—C3—C4—C5−0.9 (2)C26—N5—C24—N3179.76 (13)
O1—C4—C5—C6−179.48 (13)C26—N5—C24—C250.09 (14)
C3—C4—C5—C60.5 (2)C26—N4—C25—C24−0.25 (15)
O1—C4—C5—C7−0.1 (2)C26—N4—C25—C22179.27 (15)
C3—C4—C5—C7179.94 (12)N3—C24—C25—N4−179.58 (12)
C2—C1—C6—C5−0.3 (2)N5—C24—C25—N40.10 (15)
C4—C5—C6—C10.1 (2)N3—C24—C25—C220.8 (2)
C7—C5—C6—C1−179.32 (14)N5—C24—C25—C22−179.51 (11)
C6—C5—C7—O3177.52 (13)N1—C22—C25—N4−0.4 (2)
C4—C5—C7—O3−1.9 (2)N2—C22—C25—N4180.00 (13)
C6—C5—C7—O2−2.09 (19)N1—C22—C25—C24179.08 (13)
C4—C5—C7—O2178.54 (12)N2—C22—C25—C24−0.50 (18)
C13—C8—C9—C10−0.8 (2)C25—N4—C26—N50.31 (15)
C8—C9—C10—C110.0 (2)C24—N5—C26—N4−0.26 (16)
C9—C10—C11—O4179.69 (13)C20—C15—C16—C17−0.2 (2)
C9—C10—C11—C121.1 (2)C15—C16—C17—C181.0 (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—C21178.90 (13)
C10—C11—C12—C14177.17 (13)C16—C15—C20—O7179.13 (13)
C9—C8—C13—C120.5 (2)C16—C15—C20—C19−0.9 (2)
C11—C12—C13—C80.6 (2)C18—C19—C20—O7−178.81 (12)
C14—C12—C13—C8−177.94 (13)C21—C19—C20—O71.8 (2)
C13—C12—C14—O5−172.14 (13)C18—C19—C20—C151.2 (2)
C11—C12—C14—O59.3 (2)C21—C19—C20—C15−178.15 (13)
C13—C12—C14—O68.60 (19)C18—C19—C21—O9178.77 (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—C250.01 (19)C20—C19—C21—O8177.67 (12)
C24—N3—C23—N2−0.1 (2)

Hydrogen-bond geometry (Å, °)

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, y−1/2, −z+1/2; (iii) −x, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5001).

References

  • Forsythe, P. & Ennis, M. (1999). Inflam. Res.48, 301–307. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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